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(IUCr) Single-crystal X-ray diffraction and NMR crystallography of a 1:1 cocrystal of dithianon and pyrimethanil
<!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.0 Transitional//EN" "https://www.w3.org/TR/xhtml1/DTD/xhtml1-transitional.dtd"> <html lang="en" xmlns="https://www.w3.org/1999/xhtml" xmlns:addthis="http:://www.addthis.com/help/api-spec"> <head> <script src="https://journals.iucr.org/javascript/analytics.js"></script> <!-- Journal c --><!-- Article df3006 --> <title>(IUCr) Single-crystal X-ray diffraction and NMR crystallography of a 1:1 cocrystal of di­thia­non and pyrimethanil</title> <link href="https://purl.org/dc/elements/1.1/" rel="schema.DC" /> <link href="https://purl.org/dc/terms/" rel="schema.DCTERMS" /> <link href="https://prismstandard.org/namespaces/1.2/basic/" rel="schema.prism" /> <meta content="text/html; charset=utf-8" http-equiv="Content-Type" /> <meta content="" name="DC.coverage" /> <meta content="urn:issn:2053-2296" name="DC.source" /> <meta content="https://creativecommons.org/licenses/by/2.0/uk" name="DC.rights" /> <meta content="Pöppler, A.-C." name="DC.creator" /> <meta content="Corlett, E.K." name="DC.creator" /> <meta content="Pearce, H." name="DC.creator" /> <meta content="Seymour, M.P." name="DC.creator" /> <meta content="Reid, M." name="DC.creator" /> <meta content="Montgomery, M.G." name="DC.creator" /> <meta content="Brown, S.P." name="DC.creator" /> <meta content="2017-02-06" name="DC.date" /> <meta content="https://creativecommons.org/licenses/by/2.0/uk" name="DC.copyright" /> <meta content="doi:10.1107/S2053229617000870" name="DC.identifier" /> <meta content="International Union of Crystallography" name="DC.publisher" /> <meta content="//journals.iucr.org/paper?df3006" name="DC.link" /> <meta content="A combined single-crystal X-ray diffraction and NMR crystallography study of a 1:1 cocrystal of two fungicides, namely di­thia­non and pyrimethanil, is presented. Specifically, the role of hydrogen bonding and C—H⋯π and S⋯O inter­molecular inter­actions is qu­anti­tatively investigated." name="DC.teaser" /> <meta content="en" name="DC.language" /> <meta content="NMR CRYSTALLOGRAPHY" name="DC.subject" /> <meta content="SOLID-STATE NMR" name="DC.subject" /> <meta content="DITHIANON" name="DC.subject" /> <meta content="PYRIMETHANIL" name="DC.subject" /> <meta content="COCRYSTAL" name="DC.subject" /> <meta content="HYDROGEN BONDING" name="DC.subject" /> <meta content="C-H...[PI] INTERACTIONS" name="DC.subject" /> <meta content="FUNGICIDES" name="DC.subject" /> <meta content="A single-crystal X-ray diffraction structure of a 1:1 cocrystal of two fungicides, namely di­thia­non (DI) and pyrimethanil (PM), is reported [systematic name: 5,10-dioxo-5H,10H-naphtho­[2,3-b][1,4]dithiine-2,3-dicarbo­nitrile–4,6-dimethyl-N-phenyl­pyrimidin-2-amine (1/1), C14H4N2O2S2·C12H13N2]. Following an NMR crystallography approach, experimental solid-state magic angle spinning (MAS) NMR spectra are presented together with GIPAW (gauge-including projector augmented wave) calculations of NMR chemical shieldings. Specifically, experimental 1H and 13C chemical shifts are determined from two-dimensional 1H–13C MAS NMR correlation spectra recorded with short and longer contact times so as to probe one-bond C—H connectivities and longer-range C⋯H proximities, whereas H⋯H proximities are identified in a 1H double-quantum (DQ) MAS NMR spectrum. The performing of separate GIPAW calculations for the full periodic crystal structure and for isolated mol­ecules allows the determination of the change in chemical shift upon going from an isolated mol­ecule to the full crystal structure. For the 1H NMR chemical shifts, changes of 3.6 and 2.0 ppm correspond to inter­molecular N—H⋯O and C—H⋯O hydrogen bonding, while changes of −2.7 and −1.5 ppm are due to ring current effects associated with C—H⋯π inter­actions. Even though there is a close inter­molecular S⋯O distance of 3.10 Å, it is of note that the mol­ecule-to-crystal chemical shifts for the involved sulfur or oxygen nuclei are small." name="DC.description" /> <meta content="Single-crystal X-ray diffraction and NMR crystallography of a 1:1 cocrystal of di­thia­non and pyrimethanil" name="description" /> <meta content="text/html" name="DC.format" /> <meta content="" name="DC.relation" /> <meta content="research papers" name="DC.type" /> <meta content="Single-crystal X-ray diffraction and NMR crystallography of a 1:1 cocrystal of di­thia­non and pyrimethanil" name="DC.title" /> <meta content="Single-crystal X-ray diffraction and NMR crystallography of a 1:1 cocrystal of di­thia­non and pyrimethanil" name="title" /> <meta content="A single-crystal X-ray diffraction structure of a 1:1 cocrystal of two fungicides, namely di­thia­non (DI) and pyrimethanil (PM), is reported [systematic name: 5,10-dioxo-5H,10H-naphtho­[2,3-b][1,4]dithiine-2,3-dicarbo­nitrile–4,6-dimethyl-N-phenyl­pyrimidin-2-amine (1/1), C14H4N2O2S2·C12H13N2]. Following an NMR crystallography approach, experimental solid-state magic angle spinning (MAS) NMR spectra are presented together with GIPAW (gauge-including projector augmented wave) calculations of NMR chemical shieldings. Specifically, experimental 1H and 13C chemical shifts are determined from two-dimensional 1H–13C MAS NMR correlation spectra recorded with short and longer contact times so as to probe one-bond C—H connectivities and longer-range C⋯H proximities, whereas H⋯H proximities are identified in a 1H double-quantum (DQ) MAS NMR spectrum. The performing of separate GIPAW calculations for the full periodic crystal structure and for isolated mol­ecules allows the determination of the change in chemical shift upon going from an isolated mol­ecule to the full crystal structure. For the 1H NMR chemical shifts, changes of 3.6 and 2.0 ppm correspond to inter­molecular N—H⋯O and C—H⋯O hydrogen bonding, while changes of −2.7 and −1.5 ppm are due to ring current effects associated with C—H⋯π inter­actions. Even though there is a close inter­molecular S⋯O distance of 3.10 Å, it is of note that the mol­ecule-to-crystal chemical shifts for the involved sulfur or oxygen nuclei are small." name="DCTERMS.abstract" /> <meta content="A single-crystal X-ray diffraction structure of a 1:1 cocrystal of two fungicides, namely di­thia­non (DI) and pyrimethanil (PM), is reported [systematic name: 5,10-dioxo-5H,10H-naphtho­[2,3-b][1,4]dithiine-2,3-dicarbo­nitrile–4,6-dimethyl-N-phenyl­pyrimidin-2-amine (1/1), C14H4N2O2S2·C12H13N2]. Following an NMR crystallography approach, experimental solid-state magic angle spinning (MAS) NMR spectra are presented together with GIPAW (gauge-including projector augmented wave) calculations of NMR chemical shieldings. Specifically, experimental 1H and 13C chemical shifts are determined from two-dimensional 1H–13C MAS NMR correlation spectra recorded with short and longer contact times so as to probe one-bond C—H connectivities and longer-range C⋯H proximities, whereas H⋯H proximities are identified in a 1H double-quantum (DQ) MAS NMR spectrum. The performing of separate GIPAW calculations for the full periodic crystal structure and for isolated mol­ecules allows the determination of the change in chemical shift upon going from an isolated mol­ecule to the full crystal structure. For the 1H NMR chemical shifts, changes of 3.6 and 2.0 ppm correspond to inter­molecular N—H⋯O and C—H⋯O hydrogen bonding, while changes of −2.7 and −1.5 ppm are due to ring current effects associated with C—H⋯π inter­actions. Even though there is a close inter­molecular S⋯O distance of 3.10 Å, it is of note that the mol­ecule-to-crystal chemical shifts for the involved sulfur or oxygen nuclei are small." name="citation_abstract" /> <meta content="3" name="prism.number" /> <meta content="73" name="prism.volume" /> <meta content="2017-02-06" name="prism.publicationDate" /> <meta content="Acta Crystallographica Section C: Structural Chemistry" name="prism.publicationName" /> <meta content="https://creativecommons.org/licenses/by/2.0/uk" name="prism.copyright" /> <meta content="2053-2296" name="prism.issn" /> <meta content="research papers" name="prism.section" /> <meta content="149" name="prism.startingPage" /> <meta content="med@iucr.org" name="prism.rightsAgent" /> <meta content="156" name="prism.endingPage" /> <meta content="2053-2296" name="prism.eissn" /> <meta content="NMR CRYSTALLOGRAPHY; SOLID-STATE NMR; DITHIANON; PYRIMETHANIL; COCRYSTAL; HYDROGEN BONDING; C-H...[PI] INTERACTIONS; FUNGICIDES" name="keywords" /> <meta content="https://creativecommons.org/licenses/by/2.0/uk" name="copyright" /> <meta content="NOARCHIVE" name="ROBOTS" /> <meta content="//journals.iucr.org/c/issues/2017/03/00/df3006/" name="citation_fulltext_url" /> <meta content="156" name="citation_lastpage" /> <meta content="73" name="citation_volume" /> <meta content="Acta Cryst C" name="citation_journal_abbrev" /> <meta content="Acta Cryst Sect C" name="citation_journal_abbrev" /> <meta content="Acta Crystallogr C" name="citation_journal_abbrev" /> <meta content="Acta Crystallogr Sect C" name="citation_journal_abbrev" /> <meta content="Acta Crystallogr C Cryst Struct Commun" name="citation_journal_abbrev" /> <meta content="Acta Crystallogr Sect C Cryst Struct Commun" name="citation_journal_abbrev" /> <meta content="3" name="citation_issue" /> <meta content="149" name="citation_firstpage" /> <meta content="2017-03-01" name="citation_date" /> <meta content="2017" name="citation_year" /> <meta content="Single-crystal X-ray diffraction and NMR crystallography of a 1:1 cocrystal of di­thia­non and pyrimethanil" name="citation_title" /> <meta content="2017-02-06" name="citation_online_date" /> <meta content="Acta Crystallographica Section C: Structural Chemistry" name="citation_journal_title" /> <meta content="Pöppler, A.-C." name="citation_author" /> <meta content="Department of Physics, University of Warwick, Coventry CV4 7AL, United Kingdom" name="citation_author_institution" /> <meta content="Department of Organic Chemistry, University of Würzburg, 97074 Würzburg, Germany" name="citation_author_institution" /> <meta content="Corlett, E.K." name="citation_author" /> <meta content="Department of Physics, University of Warwick, Coventry CV4 7AL, United Kingdom" name="citation_author_institution" /> <meta content="Molecular Analytical Science Centre for Doctoral Training, University of Warwick, Coventry CV4 7AL, United Kingdom" name="citation_author_institution" /> <meta content="Pearce, H." name="citation_author" /> <meta content="Department of Physics, University of Warwick, Coventry CV4 7AL, United Kingdom" name="citation_author_institution" /> <meta content="Molecular Analytical Science Centre for Doctoral Training, University of Warwick, Coventry CV4 7AL, United Kingdom" name="citation_author_institution" /> <meta content="h.pearce@warwick.ac.uk" name="citation_author_email" /> <meta content="Seymour, M.P." name="citation_author" /> <meta content="International Research Centre, Syngenta, Jealott's Hill, Bracknell, Berkshire RG42 6EY, United Kingdom" name="citation_author_institution" /> <meta content="mark.seymour@warwick.ac.uk" name="citation_author_email" /> <meta content="Reid, M." name="citation_author" /> <meta content="International Research Centre, Syngenta, Jealott's Hill, Bracknell, Berkshire RG42 6EY, United Kingdom" name="citation_author_institution" /> <meta content="Afton Chemical, London Road, Bracknell, Berkshire RG12 2UW, United Kingdom" name="citation_author_institution" /> <meta content="matthew.reid@aftonchemical.com" name="citation_author_email" /> <meta content="Montgomery, M.G." name="citation_author" /> <meta content="International Research Centre, Syngenta, Jealott's Hill, Bracknell, Berkshire RG42 6EY, United Kingdom" name="citation_author_institution" /> <meta content="Mark.Montgomery@syngenta.com" name="citation_author_email" /> <meta content="Brown, S.P." name="citation_author" /> <meta content="Department of Physics, University of Warwick, Coventry CV4 7AL, United Kingdom" name="citation_author_institution" /> <meta content="s.p.brown@warwick.ac.uk" name="citation_author_email" /> <meta content="citation_author=Aakeroy C. 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text-align: right; width: 100px;"> <script src="//crossmark-cdn.crossref.org/widget/v2.0/widget.js"></script> <a data-target="crossmark"><img alt="CROSSMARK_Color_square_no_text.svg" src="https://crossmark-cdn.crossref.org/widget/v2.0/logos/CROSSMARK_Color_square_no_text.svg" width="60" /></a> </div> <!-- End Crossmark 2.0 widget --> <div id="aug"> <div class="au"> <b> <a href="//scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=P%26ouml%3Bppler%2C%20A%2E%2DC%2E"><span class="au">Ann-Christin Pöppler</span></a>,<a href="#oida"><sup>a,</sup></a><a href="#oidb"><sup>b</sup></a> <a href="//scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Corlett%2C%20E%2EK%2E"><span class="au">Emily K. Corlett</span></a>,<a href="#oida"><sup>a,</sup></a><a href="#oidc"><sup>c</sup></a> <a href="//scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Pearce%2C%20H%2E"><span class="au">Harriet Pearce</span></a>,<a href="#oida"><sup>a,</sup></a><a href="#oidc"><sup>c</sup></a> <a href="//scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Seymour%2C%20M%2EP%2E"><span class="au">Mark P. Seymour</span></a>,<a href="#oidd"><sup>d</sup></a> <a href="//scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Reid%2C%20M%2E"><span class="au">Matthew Reid</span></a>,<a href="#oidd"><sup>d,</sup></a><a href="#oide"><sup>e</sup></a> <a href="//scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Montgomery%2C%20M%2EG%2E"><span class="au">Mark G. Montgomery</span></a><a href="#oidd"><sup>d</sup></a> and <a href="//scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Brown%2C%20S%2EP%2E"><span class="au">Steven P. Brown</span></a><a href="#oida"><sup>a</sup></a><a href="#cor"><sup>*</sup></a></b> </div> <div id="aff"> <p><span class="font_size_2"><a id="oida"><sup><b>a</b></sup></a>Department of Physics, University of Warwick, Coventry CV4 7AL, United Kingdom, <a id="oidb"><sup><b>b</b></sup></a>Department of Organic Chemistry, University of Würzburg, 97074 Würzburg, Germany, <a id="oidc"><sup><b>c</b></sup></a>Molecular Analytical Science Centre for Doctoral Training, University of Warwick, Coventry CV4 7AL, United Kingdom, <a id="oidd"><sup><b>d</b></sup></a>International Research Centre, Syngenta, Jealott's Hill, Bracknell, Berkshire RG42 6EY, United Kingdom, and <a id="oide"><sup><b>e</b></sup></a>Afton Chemical, London Road, Bracknell, Berkshire RG12 2UW, United Kingdom<br /><a id="cor"></a><sup>*</sup>Correspondence e-mail: <a href="mailto:s.p.brown%40warwick.ac.uk">s.p.brown@warwick.ac.uk</a></span></p> </div> </div> <div id="editdetails"><span class="editor">Edited by D. L. Bryce, University of Ottawa, Canada</span> (<span class="ed_rec">Received 30 September 2016;</span> <span class="ed_acc">accepted 17 January 2017;</span> <span class="ed_web">online 6 February 2017</span>)</div> <div id="abs"> <p>A single-crystal X-ray diffraction structure of a 1:1 cocrystal of two fungicides, namely di­thia­non (DI) and pyrimethanil (PM), is reported [systematic name: 5,10-dioxo-5<span class="it"><i>H</i></span>,10<span class="it"><i>H</i></span>-naphtho­[2,3-<span class="it"><i>b</i></span>][1,4]dithiine-2,3-dicarbo­nitrile–4,6-dimethyl-<span class="it"><i>N</i></span>-phenyl­pyrimidin-2-amine (1/1), C<span class="inf"><sub>14</sub></span>H<span class="inf"><sub>4</sub></span>N<span class="inf"><sub>2</sub></span>O<span class="inf"><sub>2</sub></span>S<span class="inf"><sub>2</sub></span>·C<span class="inf"><sub>12</sub></span>H<span class="inf"><sub>13</sub></span>N<span class="inf"><sub>2</sub></span>]. Following an NMR crystallography approach, experimental solid-state magic angle spinning (MAS) NMR spectra are presented together with GIPAW (gauge-including projector augmented wave) calculations of NMR chemical shieldings. Specifically, experimental <span class="sup"><sup>1</sup></span>H and <span class="sup"><sup>13</sup></span>C chemical shifts are determined from two-dimensional <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C MAS NMR correlation spectra recorded with short and longer contact times so as to probe one-bond C—H connectivities and longer-range C⋯H proximities, whereas H⋯H proximities are identified in a <span class="sup"><sup>1</sup></span>H double-quantum (DQ) MAS NMR spectrum. The performing of separate GIPAW calculations for the full periodic <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure</a> and for isolated mol­ecules allows the determination of the change in <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> upon going from an isolated mol­ecule to the full <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure.</a> For the <span class="sup"><sup>1</sup></span>H NMR chemical shifts, changes of 3.6 and 2.0 ppm correspond to inter­molecular N—H⋯O and C—H⋯O hydrogen bonding, while changes of −2.7 and −1.5 ppm are due to ring current effects associated with C—H⋯<span class="symbol">π</span> inter­actions. Even though there is a close inter­molecular S⋯O distance of 3.10 Å, it is of note that the mol­ecule-to-crystal chemical shifts for the involved sulfur or oxygen nuclei are small.</p> </div> <div id="kwdg"> <p><span class="kwdg_head">Keywords: </span> <a href="//scripts.iucr.org/cgi-bin/full_search?words=NMR%20crystallography&Action=Search">NMR crystallography</a>; <a href="//scripts.iucr.org/cgi-bin/full_search?words=solid%2Dstate%20NMR&Action=Search">solid-state NMR</a>; <a href="//scripts.iucr.org/cgi-bin/full_search?words=di%26%23173%3Bthia%26%23173%3Bnon&Action=Search">di­thia­non</a>; <a href="//scripts.iucr.org/cgi-bin/full_search?words=pyrimethanil&Action=Search">pyrimethanil</a>; <a href="//scripts.iucr.org/cgi-bin/full_search?words=cocrystal&Action=Search">cocrystal</a>; <a href="//scripts.iucr.org/cgi-bin/full_search?words=hydrogen%20bonding&Action=Search">hydrogen bonding</a>; <a href="//scripts.iucr.org/cgi-bin/full_search?words=C%26%238212%3BH%26%238943%3B%26%23960%3B%20inter%26%23173%3Bactions&Action=Search">C—H⋯<span class="symbol">π</span> inter­actions</a>; <a href="//scripts.iucr.org/cgi-bin/full_search?words=fungicides&Action=Search">fungicides</a>.</p></div> <div class="art_codelinks"> <div class="art_codelinks_csd"><p> <span class="art_codelinks_head">CCDC reference: </span><a href="//scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1507863">1507863</a></p></div> </div> <div class="ica_readmore"> <a href="//scripts.iucr.org/cgi-bin/similar?wordList=NMR CRYSTALLOGRAPHY%20or%20SOLID-STATE NMR%20or%20DITHIANON%20or%20PYRIMETHANIL%20or%20COCRYSTAL%20or%20HYDROGEN BONDING%20or%20C-H...[PI] INTERACTIONS%20or%20FUNGICIDES&from=df3006">Similar articles</a></div> <script src="//api.growkudos.com/widgets/article/10.1107/S2053229617000870" type="text/javascript"></script> </div> </div> <div id="body"> <div class="sec1" id="DIVSEC1"> <h3><a id="SEC1"></a>1. Introduction</h3> <p>With an increasing global population, limited availability of arable land, an increase in extreme weather events and growing pest resistance to certain existing agrochemical products, innovation in the agrochemical industry is as important as ever if we are to provide enough food for everyone. With lower usage rates, ease of use and more favourable toxicology profiles being important objectives, the search for and <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/ST06981.html' onclick="return makeSubWindow("https://goldbook.iupac.org/ST06981.html", 'Navigator')">structure-based design</a> of potential agrochemical products needs to become more efficient (Lamberth <span class="it"><i>et al.</i></span>, 2013<a id="sourceBB29"></a><a href="#BB29"><img alt="[Lamberth, C., Jeanmart, S., Luksch, T. & Plant, A. (2013). Science, 341, 742-746.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Lamberth, C., Jeanmart, S., Luksch, T. & Plant, A. (2013). Science, 341, 742-746." /></a>). One possibility in this regard is the usage of cocrystals formed between an active ingredient and coformers or other active ingredients <span class="it"><i>via</i></span> reversible noncovalent inter­actions. While this is an established procedure in the development of new active pharmaceutical ingredients, where it is used to increase the solubility and bioavailability (Blagden <span class="it"><i>et al.</i></span>, 2007<a id="sourceBB9"></a><a href="#BB9"><img alt="[Blagden, N., de Matas, M., Gavan, P. T. & York, P. (2007). Adv. Drug Deliv. Rev. 59, 617-630.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Blagden, N., de Matas, M., Gavan, P. T. & York, P. (2007). Adv. Drug Deliv. Rev. 59, 617-630." /></a>), there is also great potential to exploit cocrystals in the optimization and development of agrochemicals. For example, a reduced solubility could increase the agrochemical's residence time on the respective plant and multicomponent entities could improve the release profile (and thus absolute usage), as well as allow the simultaneous delivery of two or more active components. However, the design of suitable cocrystalline materials and prediction of their properties and formed cocrystal structures is far from being trivial. Some design strategies based on the hierarchy of inter­molecular inter­actions (Aakeroy & Salmon, 2005<a id="sourceBB1"></a><a href="#BB1"><img alt="[Aakeroy, C. B. & Salmon, D. J. (2005). CrystEngComm, 7, 439-448.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Aakeroy, C. B. & Salmon, D. J. (2005). CrystEngComm, 7, 439-448." /></a>) or the assessment of the solubilities and saturation temperatures of the pure compounds to be included in a cocrystalline arrangement (ter Horst <span class="it"><i>et al.</i></span>, 2009<a id="sourceBB26"></a><a href="#BB26"><img alt="[Horst, J. H. ter, Deij, M. A. & Cains, P. W. (2009). Cryst. Growth Des. 9, 1531-1537.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Horst, J. H. ter, Deij, M. A. & Cains, P. W. (2009). Cryst. Growth Des. 9, 1531-1537." /></a>) are available as a guideline. However, if multiple and different hydrogen-bonding donors and acceptors are present in the mol­ecules, a reliable prediction of the resulting structure becomes very difficult (Bhatt <span class="it"><i>et al.</i></span>, 2009<a id="sourceBB7"></a><a href="#BB7"><img alt="[Bhatt, P. M., Azim, Y., Thakur, T. S. & Desiraju, G. R. (2009). Cryst. Growth Des. 9, 951-957.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Bhatt, P. M., Azim, Y., Thakur, T. S. & Desiraju, G. R. (2009). Cryst. Growth Des. 9, 951-957." /></a>).</p><p>NMR crystallography, namely the combination of experimental solid-state magic angle spinning (MAS) NMR with calculation of NMR parameters, is finding important application to moderately sized organic mol­ecules (Harris, 2004<a id="sourceBB23"></a><a href="#BB23"><img alt="[Harris, R. K. (2004). Solid State Sci. 6, 1025-1037.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Harris, R. K. (2004). Solid State Sci. 6, 1025-1037." /></a>; Elena <span class="it"><i>et al.</i></span>, 2006<a id="sourceBB20"></a><a href="#BB20"><img alt="[Elena, B., Pintacuda, G., Mifsud, N. & Emsley, L. (2006). J. Am. Chem. Soc. 128, 9555-9560.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Elena, B., Pintacuda, G., Mifsud, N. & Emsley, L. (2006). J. Am. Chem. Soc. 128, 9555-9560." /></a>; Harris <span class="it"><i>et al.</i></span>, 2009<a id="sourceBB25"></a><a href="#BB25"><img alt="[Harris, R. K., Wasylishen, R. E. & Duer, M. J. (2009). Editors. NMR Crystallography. Chichester: Wiley.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Harris, R. K., Wasylishen, R. E. & Duer, M. J. (2009). Editors. NMR Crystallography. Chichester: Wiley." /></a>; Bonhomme <span class="it"><i>et al.</i></span>, 2012<a id="sourceBB10"></a><a href="#BB10"><img alt="[Bonhomme, C., Gervais, C., Babonneau, F., Coelho, C., Pourpoint, F., Azais, T., Ashbrook, S. E., Griffin, J. M., Yates, J. R., Mauri, F. & Pickard, C. J. (2012). Chem. Rev. 112, 5733-5779.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Bonhomme, C., Gervais, C., Babonneau, F., Coelho, C., Pourpoint, F., Azais, T., Ashbrook, S. E., Griffin, J. M., Yates, J. R., Mauri, F. & Pickard, C. J. (2012). Chem. Rev. 112, 5733-5779." /></a>). We present here an NMR crystallography analysis of the 1:1 cocrystal of two fungicides, namely di­thia­non (DI) and pyrimethanil (PM). Specifically, following a preparation protocol in Sowa <span class="it"><i>et al.</i></span> (2013<a id="sourceBB46"></a><a href="#BB46"><img alt="[Sowa, C., Saxell, H. E. & Vogel, R. (2013). EU Patent EP 2197278.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Sowa, C., Saxell, H. E. & Vogel, R. (2013). EU Patent EP 2197278." /></a>), a single-crystal X-ray diffraction <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Structure_determination' onclick="return makeSubWindow("https://dictionary.iucr.org/Structure_determination", 'Navigator')">structure determination</a> is reported, with this structure (after DFT geometry optimization) providing the input for a calculation, using the GIPAW (gauge-including projector augmented wave) method (Pickard & Mauri, 2001<a id="sourceBB38"></a><a href="#BB38"><img alt="[Pickard, C. J. & Mauri, F. (2001). Phys. Rev. B 63, 245101.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Pickard, C. J. & Mauri, F. (2001). Phys. Rev. B 63, 245101." /></a>; Yates <span class="it"><i>et al.</i></span>, 2007<a id="sourceBB55"></a><a href="#BB55"><img alt="[Yates, J. R., Pickard, C. J. & Mauri, F. (2007). Phys. Rev. B, 76, 024401.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Yates, J. R., Pickard, C. J. & Mauri, F. (2007). Phys. Rev. B, 76, 024401." /></a>), of the NMR chemical shieldings. The computational analysis is complemented by the recording of 1D (one-dimensional) and 2D (two-dimensional) experimental <span class="sup"><sup>1</sup></span>H and <span class="sup"><sup>13</sup></span>C MAS NMR spectra. Building upon studies of pharmaceutical cocrystals by such an NMR crystallography investigation (Tatton <span class="it"><i>et al.</i></span>, 2013<a id="sourceBB48"></a><a href="#BB48"><img alt="[Tatton, A. S., Pham, T. N., Vogt, F. G., Iuga, D., Edwards, A. J. & Brown, S. P. (2013). Mol. Pharm. 10, 999-1007.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Tatton, A. S., Pham, T. N., Vogt, F. G., Iuga, D., Edwards, A. J. & Brown, S. P. (2013). Mol. Pharm. 10, 999-1007." /></a>; Dudenko <span class="it"><i>et al.</i></span>, 2013<a id="sourceBB19"></a><a href="#BB19"><img alt="[Dudenko, D. V., Yates, J. R., Harris, K. D. M. & Brown, S. P. (2013). CrystEngComm, 15, 8797-8807.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Dudenko, D. V., Yates, J. R., Harris, K. D. M. & Brown, S. P. (2013). CrystEngComm, 15, 8797-8807." /></a>; Stevens <span class="it"><i>et al.</i></span>, 2014<a id="sourceBB47"></a><a href="#BB47"><img alt="[Stevens, J. S., Byard, S. J., Seaton, C. C., Sadiq, G., Davey, R. J. & Schroeder, S. L. M. (2014). Phys. Chem. Chem. Phys. 16, 1150-1160.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Stevens, J. S., Byard, S. J., Seaton, C. C., Sadiq, G., Davey, R. J. & Schroeder, S. L. M. (2014). Phys. Chem. Chem. Phys. 16, 1150-1160." /></a>; Kerr <span class="it"><i>et al.</i></span>, 2015<a id="sourceBB28"></a><a href="#BB28"><img alt="[Kerr, H. E., Softley, L. K., Suresh, K., Nangia, A., Hodgkinson, P. & Evans, I. R. (2015). CrystEngComm, 17, 6707-6715.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Kerr, H. E., Softley, L. K., Suresh, K., Nangia, A., Hodgkinson, P. & Evans, I. R. (2015). CrystEngComm, 17, 6707-6715." /></a>; Sardo <span class="it"><i>et al.</i></span>, 2015<a id="sourceBB41"></a><a href="#BB41"><img alt="[Sardo, M., Santos, S. M., Babaryk, A. A., Lopez, C., Alkorta, I., Elguero, J., Claramunt, R. M. & Mafra, L. (2015). Solid State Nucl. Magn. Reson. 65, 49-63.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Sardo, M., Santos, S. M., Babaryk, A. A., Lopez, C., Alkorta, I., Elguero, J., Claramunt, R. M. & Mafra, L. (2015). Solid State Nucl. Magn. Reson. 65, 49-63." /></a>; Luedeker <span class="it"><i>et al.</i></span>, 2016<a id="sourceBB31"></a><a href="#BB31"><img alt="[Luedeker, D., Gossmann, R., Langer, K. & Brunklaus, G. (2016). Cryst. Growth Des. 16, 3087-3100.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Luedeker, D., Gossmann, R., Langer, K. & Brunklaus, G. (2016). Cryst. Growth Des. 16, 3087-3100." /></a>), we present here the application of this approach to an agrochemical cocrystal.</p></div> <div class="sec1" id="DIVSEC2"> <h3><a id="SEC2"></a>2. Experimental and computational details</h3> <div class="sec2" id="DIVSEC2.1"> <h4><a id="SEC2.1"></a>2.1. Sample preparation</h4> <p>The DI–PM cocrystal was prepared according to method VII in point [0041] of Sowa <span class="it"><i>et al.</i></span> (2013<a href="#BB46"><img alt="[Sowa, C., Saxell, H. E. & Vogel, R. (2013). EU Patent EP 2197278.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Sowa, C., Saxell, H. E. & Vogel, R. (2013). EU Patent EP 2197278." /></a>), <span class="it"><i>i.e.</i></span> dry di­thia­non and pyrimethanil (both solids) were mixed thoroughly in a 1:1 molar ratio (0.5 g of pyrimethanil) and kept at 323 K under agitation. After a couple of hours, the powdery product had changed to a dark-olive-green colour.</p> <div class="scheme"><a id="SCHEME1"></a> <img alt="[Scheme 1]" src="df3006scheme1.gif" /> </div> </div> <div class="sec2" id="DIVSEC2.2"> <h4><a id="SEC2.2"></a>2.2. Single-crystal X-ray diffraction: structure solution and refinement</h4> <p>Crystal data, data collection and structure <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Refinement' onclick="return makeSubWindow("https://dictionary.iucr.org/Refinement", 'Navigator')">refinement</a> details are summarized in Table 1<a href="#TABLE1"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>. The H atoms were all located in a difference map, but those attached to C atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry [C—H = 0.93–0.98 Å and N—H = 0.86–0.89 Å, and with <span class="it"><i>U</i></span><span class="inf"><sub>iso</sub></span>(H) = 1.2–1.5<span class="it"><i>U</i></span><span class="inf"><sub>eq</sub></span>(parent)], after which the positions were refined with riding constraints (Cooper <span class="it"><i>et al.</i></span>, 2010<a id="sourceBB17"></a><a href="#BB17"><img alt="[Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107." /></a>).</p><div class="table"> <table cellpadding="2" class="bgcolor_FFCCCC" summary="Experimental details" width="100%"> <tbody> <tr> <td> <table class="bgcolor_FFCCCC tbheader" summary="Experimental details" width="100%"> <tbody> <tr> <td align="left" class="bgcolor_FFCCCC" valign="bottom"> <p><span class="font_size_3 table_number"><b><a id="TABLE1">Table 1</a></b></span><br /><span class="font_size_2 tbcaption">Experimental details</span> </p></td> </tr> </tbody> </table> <table class="bgcolor_FFCCCC tbheader" summary="Experimental details" width="100%"> <tbody> <tr> <td align="left" class="bgcolor_FFCCCC" valign="bottom"> </td> </tr> </tbody> </table> <table summary="Experimental details" width="100%"> <tbody valign="top"> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="2" rowspan="1" valign="top"><span class="font_size_2 table_entry">Crystal data</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Chemical formula</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C<span class="inf"><sub>14</sub></span>H<span class="inf"><sub>4</sub></span>N<span class="inf"><sub>2</sub></span>O<span class="inf"><sub>2</sub></span>S<span class="inf"><sub>2</sub></span>·C<span class="inf"><sub>12</sub></span>H<span class="inf"><sub>13</sub></span>N<span class="inf"><sub>3</sub></span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>M</i></span><span class="inf"><sub>r</sub></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">495.59</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Crystal system, space group</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Monoclinic, <span class="it"><i>P</i></span>2<span class="inf"><sub>1</sub></span>/<span class="it"><i>n</i></span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Temperature (K)</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">100</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>a</i></span>, <span class="it"><i>b</i></span>, <span class="it"><i>c</i></span> (Å)</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.1707 (2), 22.8006 (6), 13.8237 (4)</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="symbol">β</span> (°)</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">97.047 (3)</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>V</i></span> (Å<span class="sup"><sup>3</sup></span>)</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">2243.04 (7)</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>Z</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">4</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Radiation type</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Cu <span class="it"><i>K</i></span><span class="symbol">α</span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="symbol">μ</span> (mm<span class="sup"><sup>−1</sup></span>)</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">2.45</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Crystal size (mm)</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.60 × 0.10 × 0.02</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="2" rowspan="1" valign="top"><span class="font_size_2 table_entry"> </span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="2" rowspan="1" valign="top"><span class="font_size_2 table_entry">Data collection</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Diffractometer</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Agilent Xcalibur Onyx Ultra</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Absorption correction</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">Multi-scan (<span class="it"><i>CrysAlis PRO</i></span>; Agilent, 2014<a id="sourceBB3"></a><a href="#BB3"><img alt="[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England." /></a>)</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>T</i></span><span class="inf"><sub>min</sub></span>, <span class="it"><i>T</i></span><span class="inf"><sub>max</sub></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.596, 1.000</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">No. of measured, independent and observed [<span class="it"><i>I</i></span> > 2.0<span class="symbol">σ</span>(<span class="it"><i>I</i></span>)] reflections</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">5143, 3160, 2667</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>R</i></span><span class="inf"><sub>int</sub></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.035</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="symbol">θ</span><span class="inf"><sub>max</sub></span> (°)</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">58.9</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">(sin <span class="symbol">θ</span>/<span class="symbol">λ</span>)<span class="inf"><sub>max</sub></span> (Å<span class="sup"><sup>−1</sup></span>)</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.556</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="2" rowspan="1" valign="top"><span class="font_size_2 table_entry"> </span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="2" rowspan="1" valign="top"><span class="font_size_2 table_entry">Refinement</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>R</i></span>[<span class="it"><i>F</i></span><span class="sup"><sup>2</sup></span> > 2<span class="symbol">σ</span>(<span class="it"><i>F</i></span><span class="sup"><sup>2</sup></span>)], <span class="it"><i>wR</i></span>(<span class="it"><i>F</i></span><span class="sup"><sup>2</sup></span>), <span class="it"><i>S</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.045, 0.094, 0.98</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">No. of reflections</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">3141</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">No. of parameters</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">109</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">No. of restraints</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">3</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H-atom treatment</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H atoms treated by a mixture of independent and constrained refinement</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="symbol">Δ</span><span class="symbol">ρ</span><span class="inf"><sub>max</sub></span>, <span class="symbol">Δ</span><span class="symbol">ρ</span><span class="inf"><sub>min</sub></span> (e Å<span class="sup"><sup>−3</sup></span>)</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.43, −0.37</span></td> </tr> <tr><td colspan="2"><span class="font_size_2 tfnu"><a id="TABLE1_TFNU1"></a>Computer programs: <span class="it"><i>CrysAlis PRO</i></span> (Agilent, 2014<a href="#BB3"><img alt="[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England." /></a>), <span class="it"><i>SUPERFLIP</i></span> (Palatinus & Chapuis, 2007<a id="sourceBB36"></a><a href="#BB36"><img alt="[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790." /></a>), <span class="it"><i>CRYSTALS</i></span> (Betteridge <span class="it"><i>et al.</i></span>, 2003<a id="sourceBB6"></a><a href="#BB6"><img alt="[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487." /></a>), <span class="it"><i>CAMERON</i></span> (Watkin <span class="it"><i>et al.</i></span>, 1996<a id="sourceBB51"></a><a href="#BB51"><img alt="[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England." /></a>) and <span class="it"><i>Mercury</i></span> (Macrae <span class="it"><i>et al.</i></span>, 2006<a id="sourceBB32"></a><a href="#BB32"><img alt="[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457." /></a>). <br /></span> </td></tr></tbody> </table> </td> </tr> </tbody> </table> </div> </div> <div class="sec2" id="DIVSEC2.3"> <h4><a id="SEC2.3"></a>2.3. Solid-state NMR</h4> <p>1D <span class="sup"><sup>1</sup></span>H MAS and 1D <span class="sup"><sup>13</sup></span>C cross polarization (CP) MAS experiments were performed on a Bruker Avance III spectrometer operating at <span class="sup"><sup>1</sup></span>H and <span class="sup"><sup>13</sup></span>C Larmor frequencies of 600 and 150.9 MHz, respectively, using a 1.3 mm HXY (<span class="sup"><sup>1</sup></span>H MAS) or a 4 mm HX (<span class="sup"><sup>13</sup></span>C CP MAS) Bruker probe. In all cases, a <span class="sup"><sup>1</sup></span>H 90° <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/P04947.html' onclick="return makeSubWindow("https://goldbook.iupac.org/P04947.html", 'Navigator')">pulse duration</a> of 2.5 µs was used. 2D <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C HETCOR experiments were performed on a Bruker Avance III spectrometer, using a 4 mm HXY probe in double-resonance mode. In the HETCOR pulse sequence, the following phase cycling was employed: <span class="sup"><sup>1</sup></span>H 90° pulse (90° 270°), <span class="sup"><sup>13</sup></span>C 180° pulse (2{0°} 2{180°}), <span class="sup"><sup>13</sup></span>C CP contact pulse (4{0°} 4{180°} 4{90°} 4{270°}), receiver (0° 180° 0° 180° 180° 0° 180° 0° 90° 270° 90° 270° 270° 90° 270° 90°). For CP, a 70 to 100% ramp (Metz <span class="it"><i>et al.</i></span>, 1994<a id="sourceBB34"></a><a href="#BB34"><img alt="[Metz, G., Wu, X. L. & Smith, S. O. (1994). J. Magn. Reson. Ser. A, 110, 219-227.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Metz, G., Wu, X. L. & Smith, S. O. (1994). J. Magn. Reson. Ser. A, 110, 219-227." /></a>) on the <span class="sup"><sup>1</sup></span>H channel was used for the CP contact time. During acquisition of a <span class="sup"><sup>13</sup></span>C FID, SPINAL64 (Fung <span class="it"><i>et al.</i></span>, 2000<a id="sourceBB21"></a><a href="#BB21"><img alt="[Fung, B. M., Khitrin, A. K. & Ermolaev, K. (2000). J. Magn. Reson. 142, 97-101.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Fung, B. M., Khitrin, A. K. & Ermolaev, K. (2000). J. Magn. Reson. 142, 97-101." /></a>) <span class="sup"><sup>1</sup></span>H heteronuclear decoupling was applied with a <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/P04947.html' onclick="return makeSubWindow("https://goldbook.iupac.org/P04947.html", 'Navigator')">pulse duration</a> of 5.9 µs at a nutation frequency of 100 kHz. A 2D <span class="sup"><sup>1</sup></span>H DQ experiment with BABA recoupling (Sommer <span class="it"><i>et al.</i></span>, 1995<a id="sourceBB45"></a><a href="#BB45"><img alt="[Sommer, W., Gottwald, J., Demco, D. E. & Spiess, H. W. (1995). J. Magn. Reson. Ser. A, 113, 131-134.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Sommer, W., Gottwald, J., Demco, D. E. & Spiess, H. W. (1995). J. Magn. Reson. Ser. A, 113, 131-134." /></a>; Schnell <span class="it"><i>et al.</i></span>, 1998<a id="sourceBB43"></a><a href="#BB43"><img alt="[Schnell, I., Lupulescu, A., Hafner, S., Demco, D. E. & Spiess, H. W. (1998). J. Magn. Reson. 133, 61-69.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Schnell, I., Lupulescu, A., Hafner, S., Demco, D. E. & Spiess, H. W. (1998). J. Magn. Reson. 133, 61-69." /></a>) was performed on a Bruker Avance III spectrometer operating at a <span class="sup"><sup>1</sup></span>H Larmor frequency of 700 MHz using a 1.3 mm HXY Bruker probe. A 16-step phase cycle was used to select <span class="symbol">Δ</span><span class="it"><i>p</i></span> = ±2 on the DQ excitation block and <span class="symbol">Δ</span><span class="it"><i>p</i></span> = −1 on the <span class="it"><i>z</i></span>-filter 90° pulse, where <span class="it"><i>p</i></span> is the coherence order. In all 2D experiments, the States–TPPI method was used to achieve sign discrimination in <span class="it"><i>F</i></span><span class="inf"><sub>1</sub></span>. <span class="sup"><sup>13</sup></span>C and <span class="sup"><sup>1</sup></span>H chemical shifts are referenced with respect to TMS using <span class="scp"><!-- font_size_2 -->L<!-- end of font_size_2 --></span>-alanine at natural abundance as an external reference: 177.8 ppm for the <span class="sup"><sup>13</sup></span>C carboxyl­ate resonance and 1.1 ppm for the <span class="sup"><sup>1</sup></span>H methyl resonance. All experiments were performed at room temperature, though frictional effects due to MAS increase the actual sample temperature (Langer <span class="it"><i>et al.</i></span>, 1999<a id="sourceBB30"></a><a href="#BB30"><img alt="[Langer, B., Schnell, I., Spiess, H. W. & Grimmer, A. R. (1999). J. Magn. Reson. 138, 182-186.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Langer, B., Schnell, I., Spiess, H. W. & Grimmer, A. R. (1999). J. Magn. Reson. 138, 182-186." /></a>).</p></div> <div class="sec2" id="DIVSEC2.4"> <h4><a id="SEC2.4"></a>2.4. DFT calculations</h4> <p>Calculations were performed using <span class="it"><i>CASTEP</i></span> (Clark <span class="it"><i>et al.</i></span>, 2005<a id="sourceBB16"></a><a href="#BB16"><img alt="[Clark, S. J., Segall, M. D., Pickard, C. J., Hasnip, P. J., Probert, M. J., Refson, K. & Payne, M. C. (2005). Z. Kristallogr. 220, 567-570.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Clark, S. J., Segall, M. D., Pickard, C. J., Hasnip, P. J., Probert, M. J., Refson, K. & Payne, M. C. (2005). Z. Kristallogr. 220, 567-570." /></a>; Academic Release Version 8.0) and employed the PBE exchange-correlational functional (Perdew <span class="it"><i>et al.</i></span>, 1996<a id="sourceBB37"></a><a href="#BB37"><img alt="[Perdew, J. P., Burke, K. & Ernzerhof, M. (1996). Phys. Rev. Lett. 77, 3865-3868.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Perdew, J. P., Burke, K. & Ernzerhof, M. (1996). Phys. Rev. Lett. 77, 3865-3868." /></a>). For both geometry optimization and NMR shielding calculations, a plane-wave basis set with ultrasoft pseudopotentials (Vanderbilt, 1990<a id="sourceBB50"></a><a href="#BB50"><img alt="[Vanderbilt, D. (1990). Phys. Rev. B, 41, 7892.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Vanderbilt, D. (1990). Phys. Rev. B, 41, 7892." /></a>) with a maximum plane-wave cut-off energy of 700 eV was used. A Monkhorst–Pack grid of minimum sample spacing 0.05 × 2<span class="symbol">π</span> Å<span class="sup"><sup>−1</sup></span> was used to take integrals over the <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Brillouin_zone' onclick="return makeSubWindow("https://dictionary.iucr.org/Brillouin_zone", 'Navigator')">Brillouin zone.</a> Geometry optimization was performed with the unit-cell parameters fixed, starting from the single-crystal X-ray structure. The positions of the 208 atoms in the <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Unit_cell' onclick="return makeSubWindow("https://dictionary.iucr.org/Unit_cell", 'Navigator')">unit cell</a> (<span class="it"><i>Z</i></span> = 4, <span class="it"><i>Z</i></span>′ = 1) were relaxed and periodic boundary conditions were applied. The <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Space_group' onclick="return makeSubWindow("https://dictionary.iucr.org/Space_group", 'Navigator')">space group</a> <span class="it"><i>P</i></span>2<span class="inf"><sub>1</sub></span>/<span class="it"><i>n</i></span> was preserved. All distances and angles stated in the main text of this article are for the geometry-optimized <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure.</a> Note also that the geometry optimization within <span class="it"><i>CASTEP</i></span> causes a relabelling of the atoms – in this article, we use the <span class="it"><i>CASTEP</i></span> numbering; see Fig. S1 in the <a href="//scripts.iucr.org/cgi-bin/sendsup?df3006"><span class="it"><i>Supporting information</i></span></a> for a comparison with the numbering employed in the crystallographic <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/CIF' onclick="return makeSubWindow("https://dictionary.iucr.org/CIF", 'Navigator')">CIF</a> file. The GIPAW method (Pickard & Mauri, 2001<a href="#BB38"><img alt="[Pickard, C. J. & Mauri, F. (2001). Phys. Rev. B 63, 245101.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Pickard, C. J. & Mauri, F. (2001). Phys. Rev. B 63, 245101." /></a>; Yates <span class="it"><i>et al.</i></span>, 2007<a href="#BB55"><img alt="[Yates, J. R., Pickard, C. J. & Mauri, F. (2007). Phys. Rev. B, 76, 024401.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Yates, J. R., Pickard, C. J. & Mauri, F. (2007). Phys. Rev. B, 76, 024401." /></a>) was utilized for the NMR chemical-shielding calculations, which were performed on the geometry-optimized structure. For the isolated mol­ecule calculations, a single mol­ecule (either DI or PM) from the fully geometry optimized structure is kept in the <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Unit_cell' onclick="return makeSubWindow("https://dictionary.iucr.org/Unit_cell", 'Navigator')">unit cell,</a> whose dimensions are also increased by ∼5 Å in each direction – the NMR shieldings are then calculated without any further geometry optimization.</p></div> </div> <div class="sec1" id="DIVSEC3"> <h3><a id="SEC3"></a>3. Results and discussion</h3> <div class="sec2" id="DIVSEC3.1"> <h4><a id="SEC3.1"></a>3.1. Single-crystal X-ray diffraction structure</h4> <p>The single-crystal X-ray diffraction structure of the DI–PM cocrystal is schematically represented in Fig. 1<a href="#FIG1"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>. As shown in Fig. 1<a href="#FIG1"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>a</i></span>), a chain of mol­ecules is held together by N—H⋯O and C—H⋯O hydrogen bonds (between DI and PM mol­ecules) and by putative S⋯O inter­actions (Burling & Goldstein, 1992<a id="sourceBB15"></a><a href="#BB15"><img alt="[Burling, F. T. & Goldstein, B. M. (1992). J. Am. Chem. Soc. 114, 2313-2320.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Burling, F. T. & Goldstein, B. M. (1992). J. Am. Chem. Soc. 114, 2313-2320." /></a>) between two DI mol­ecules; note that the relative strengths of these inter­actions is investigated below (see §3.5<a href="#SEC3.5"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>) using GIPAW calculations of NMR chemical shieldings. The further packing of two chains of mol­ecules as `layers' and a `zigzag' arrangement of chains are shown in Figs. 1<a href="#FIG1"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>b</i></span>) and 1(<span class="it"><i>c</i></span>), respectively. As can be seen from the representation along the crystallographic <span class="it"><i>a</i></span> axis in Fig. 1<a href="#FIG1"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>), the packing is based on assemblies of blocks of four mol­ecules; four mol­ecules (PM–DI–DI–PM) are arranged in a layer (Fig. 1<a href="#FIG1"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>a</i></span>), forming a block that is perpendicular to an adjacent block of four mol­ecules, thus building up the `zigzag' arrangement.</p><div class="fig"> <table cellpadding="5" class="fig" summary="Figure 1" width="100%"> <tbody> <tr> <td class="td_align_center width_20"> <a href="df3006fig1.html"><img alt="[Figure 1]" class="figlnkthm img_align_middle" src="df3006fig1thm.gif" /> <br /></a> </td> <td> <span class="font_size_3"><b><a href="df3006fig1.html" id="FIG1">Figure 1</a></b></span> <br /><span class="font_size_2 caption">Representations of the crystal structure of the DI–PM cocrystal, showing (<span class="it"><i>a</i></span>) the inter­molecular inter­actions within a `chain' of mol­ecules, with displacement ellipsoids drawn at the 50% probability level, (<span class="it"><i>b</i></span>) the packing of two chains of mol­ecules as `layers' and (<span class="it"><i>c</i></span>) the `zigzag' arrangement of chains (viewed along the crystallographic <span class="it"><i>a</i></span> axis). In parts (<span class="it"><i>b</i></span>) and (<span class="it"><i>c</i></span>), the <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Unit_cell' onclick="return makeSubWindow("https://dictionary.iucr.org/Unit_cell", 'Navigator')">unit cell</a> is shown, indicating the <span class="it"><i>a</i></span>, <span class="it"><i>b</i></span> and <span class="it"><i>c</i></span> unit-cell axes.</span></td> </tr> </tbody> </table> </div> </div> <div class="sec2" id="DIVSEC3.2"> <h4><a id="SEC3.2"></a>3.2. Experimental and calculated <span class="sup"><sup>13</sup></span>C chemical shifts</h4> <p>Fig. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a> presents a <span class="sup"><sup>13</sup></span>C CP MAS NMR 1D spectrum (Fig. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>a</i></span>) of the DI–PM cocrystal, together with three stick spectra (Figs. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>b</i></span>, 2<span class="it"><i>c</i></span> and 2<span class="it"><i>d</i></span>) that represent <span class="sup"><sup>13</sup></span>C chemical shifts calculated using the GIPAW method for the DI–PM <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure.</a> Specifically, the calculated <span class="sup"><sup>13</sup></span>C chemical shifts are presented in three groups according to whether they correspond to direct one-bond C—H connectivities (Fig. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>b</i></span>, red labels) or nonprotonated C atoms (Figs. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>c</i></span> and 2<span class="it"><i>d</i></span>, blue and green labels, respectively). The distinction between Figs. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>) and 2(<span class="it"><i>d</i></span>) corresponds to whether cross peaks corresponding to a longer-range C⋯H proximity are observed in <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C 2D correlation spectra (see §3.4<a href="#SEC3.4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>).</p><div class="fig"> <table cellpadding="5" class="fig" summary="Figure 2" width="100%"> <tbody> <tr> <td class="td_align_center width_20"> <a href="df3006fig2.html"><img alt="[Figure 2]" class="figlnkthm img_align_middle" src="df3006fig2thm.gif" /> <br /></a> </td> <td> <span class="font_size_3"><b><a href="df3006fig2.html" id="FIG2">Figure 2</a></b></span> <br /><span class="font_size_2 caption">(<span class="it"><i>a</i></span>) A <span class="sup"><sup>1</sup></span>H (600 MHz)–<span class="sup"><sup>13</sup></span>C CP MAS (12.5 kHz) NMR spectrum of the DI–PM cocrystal (* denote spinning sidebands), together with (<span class="it"><i>b</i></span>)–(<span class="it"><i>d</i></span>) stick spectra corresponding to calculated (GIPAW) <span class="sup"><sup>13</sup></span>C chemical shifts (see Table 2<a href="#TABLE2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>). Separate stick spectra are presented according to whether correlation peaks corresponding to (<span class="it"><i>b</i></span>) direct C—H bonds or (<span class="it"><i>c</i></span>) longer-range C⋯H proximities are observed in the <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C 2D spectra presented in Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>, or (<span class="it"><i>d</i></span>) where no experimental correlation peaks are observed. In the CP MAS experiment, a contact time of 1.4 ms was used and 1024 transients were co-added for a recycle delay of 57 s.</span></td> </tr> </tbody> </table> </div> </div> <div class="sec2" id="DIVSEC3.3"> <h4><a id="SEC3.3"></a>3.3. One- and two-dimensional <span class="sup"><sup>1</sup></span>H MAS NMR spectra</h4> <p>Figs. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>a</i></span>) and 3(<span class="it"><i>b</i></span>) present <span class="sup"><sup>1</sup></span>H NMR spectra of the DI–PM cocrystal recorded at a fast MAS frequency of 60 kHz; specifically, a one-pulse one-dimensional spectrum in Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>a</i></span>), together with vertical lines corresponding to calculated (GIPAW) <span class="sup"><sup>1</sup></span>H chemical shifts, as well as a 2D DQ spectrum in Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>b</i></span>). In addition, Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>) presents a <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C 2D correlation spectrum of the DI–PM cocrystal; note that this spectrum has been rotated through 90° from its usual representation such that the direct (<span class="sup"><sup>13</sup></span>C) dimension is vertical. In this way, it is possible to directly compare (see vertical dashed lines) <span class="sup"><sup>1</sup></span>H chemical shifts of peaks in the <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C (Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>c</i></span>) and <span class="sup"><sup>1</sup></span>H DQ 2D (Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>b</i></span>) and <span class="sup"><sup>1</sup></span>H 1D (Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>a</i></span>) spectra. Two separate spectral regions are presented in Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>) corresponding to (top) the methyl resonances at a <span class="sup"><sup>13</sup></span>C <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> close to 25 ppm and (bottom) the aromatic CH resonances with <span class="sup"><sup>13</sup></span>C chemical shifts between 110 and 140 ppm.</p><div class="fig"> <table cellpadding="5" class="fig" summary="Figure 3" width="100%"> <tbody> <tr> <td class="td_align_center width_20"> <a href="df3006fig3.html"><img alt="[Figure 3]" class="figlnkthm img_align_middle" src="df3006fig3thm.gif" /> <br /></a> </td> <td> <span class="font_size_3"><b><a href="df3006fig3.html" id="FIG3">Figure 3</a></b></span> <br /><span class="font_size_2 caption">MAS NMR spectra of the DI–PM cocrystal, showing (<span class="it"><i>a</i></span>) a <span class="sup"><sup>1</sup></span>H (600 MHz) MAS (60 kHz) one-pulse spectrum (16 transients were co-added for a recycle delay of 15 s), (<span class="it"><i>b</i></span>) a 2D <span class="sup"><sup>1</sup></span>H (700 MHz) DQ MAS (60 kHz) spectrum (the dashed diagonal line indicates the <span class="it"><i>F</i></span><span class="inf"><sub>1</sub></span> = 2<span class="it"><i>F</i></span><span class="inf"><sub>2</sub></span> DQ–SQ diagonal) recorded using one rotor period of BABA recoupling (32 transients were co-added for each of 200 <span class="it"><i>t</i></span><span class="inf"><sub>1</sub></span> FIDs using a recycle delay of 6 s, corresponding to a total experiment time of 12 h) and (<span class="it"><i>c</i></span>) a <span class="sup"><sup>1</sup></span>H (500 MHz)–<span class="sup"><sup>13</sup></span>C HETCOR MAS (12.5 kHz) spectrum recorded using FSLG <span class="sup"><sup>1</sup></span>H homonuclear decoupling in <span class="it"><i>t</i></span><span class="inf"><sub>1</sub></span> and a short CP transfer duration of 100 µs (104 transients were co-added for each of 128 <span class="it"><i>t</i></span><span class="inf"><sub>1</sub></span> FIDs using a recycle delay of 6 s, corresponding to a total experimental time of 22 h). The vertical lines in part (<span class="it"><i>a</i></span>) correspond to calculated (GIPAW) <span class="sup"><sup>1</sup></span>H chemical shifts. For the <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C NMR spectrum in part (<span class="it"><i>c</i></span>), two separate spectral regions are presented corresponding to methyl and aromatic C—H groups; note that this spectrum has been rotated through 90° from its usual representation [the <span class="sup"><sup>13</sup></span>C dimension corresponds to direct (<span class="it"><i>t</i></span><span class="inf"><sub>2</sub></span>) acquisition]. The base contour level is at (<span class="it"><i>b</i></span>) 7% and (<span class="it"><i>c</i></span>) 20% of the maximum peak height.</span></td> </tr> </tbody> </table> </div> <p>The <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C correlation spectrum in Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>) was recorded using a short CP contact time of 100 µs to transfer magnetization from <span class="sup"><sup>1</sup></span>H to <span class="sup"><sup>13</sup></span>C, such that cross peaks correspond to one-bond C—H connectivities. The spreading of the resonances into two dimensions in Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>) allows the identification of two and ten resolved cross peaks for the CH<span class="inf"><sub>3</sub></span> and aromatic CH groups, respectively. The value of such a <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C correlation spectrum in resolving and assigning the experimental <span class="sup"><sup>1</sup></span>H chemical shifts is thus evident. Table 2<a href="#TABLE2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a> lists the calculated (GIPAW) and experimental <span class="sup"><sup>13</sup></span>C chemical shifts (sorted in order of increasing chemical shift). For directly bonded C—H connectivities, H-atom labels and calculated (GIPAW) and experimental <span class="sup"><sup>1</sup></span>H chemical shifts are presented in normal font.</p><div class="table"> <table cellpadding="2" class="bgcolor_FFCCCC" summary="Comparison of calculated (GIPAW)a and experimental 13C and 1H NMR chemical shifts (in ppm) in the DI–PM cocrystalb" width="100%"> <tbody> <tr> <td> <table class="bgcolor_FFCCCC tbheader" summary="Comparison of calculated (GIPAW)a and experimental 13C and 1H NMR chemical shifts (in ppm) in the DI–PM cocrystalb" width="100%"> <tbody> <tr> <td align="left" class="bgcolor_FFCCCC" valign="bottom"> <p><span class="font_size_3 table_number"><b><a id="TABLE2">Table 2</a></b></span><br /><span class="font_size_2 tbcaption">Comparison of calculated (GIPAW)<span class="sup"><sup><span class="it"><i>a</i></span></sup></span> and experimental <span class="sup"><sup>13</sup></span>C and <span class="sup"><sup>1</sup></span>H NMR chemical shifts (in ppm) in the DI–PM cocrystal<span class="sup"><sup><span class="it"><i>b</i></span></sup></span></span> </p></td> </tr> </tbody> </table> <table class="bgcolor_FFCCCC tbheader" summary="Comparison of calculated (GIPAW)a and experimental 13C and 1H NMR chemical shifts (in ppm) in the DI–PM cocrystalb" width="100%"> <tbody> <tr> <td align="left" class="bgcolor_FFCCCC" valign="bottom"> </td> </tr> </tbody> </table> <table summary="Comparison of calculated (GIPAW)a and experimental 13C and 1H NMR chemical shifts (in ppm) in the DI–PM cocrystalb" width="100%"> <thead valign="bottom"> <tr> <th align="center" class="bgcolor_FFFFFF" colspan="2" rowspan="1" valign="bottom"><span class="font_size_2">Atom label</span></th> <th align="center" class="bgcolor_FFFFFF" colspan="2" rowspan="1" valign="bottom"><span class="font_size_2"><span class="sup"><sup>13</sup></span>C</span></th> <th align="center" class="bgcolor_FFFFFF" colspan="2" rowspan="1" valign="bottom"><span class="font_size_2"><span class="sup"><sup>1</sup></span>H</span></th> </tr> </thead> <tbody valign="top"> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="symbol">δ</span><span class="inf"><sub>calc</sub></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="symbol">δ</span><span class="inf"><sub>expt</sub></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="symbol">δ</span><span class="inf"><sub>calc</sub></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="symbol">δ</span><span class="inf"><sub>expt</sub></span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C65</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H22/H23/H24<span class="sup"><sup><span class="it"><i>c</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">15.3</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">23.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">1.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">1.9</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C68</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H26/H27/H28<span class="sup"><sup><span class="it"><i>c</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">17.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">25.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">2.0</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">2.0</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C66</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H25</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">111.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">112.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">3.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">4.0</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">113.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">114.4<span class="sup"><sup><span class="it"><i>d</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C14</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">114.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">114.4<span class="sup"><sup><span class="it"><i>d</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">115.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">114.4<span class="sup"><sup><span class="it"><i>d</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C13</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">115.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">114.4<span class="sup"><sup><span class="it"><i>d</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C58</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H17</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">120.1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">119.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">9.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">9.1</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C62</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H21</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">120.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">120.3</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">8.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">8.0</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">126.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">125.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.4</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>H1<span class="sup"><sup><span class="it"><i>e</i></span></sup></span></i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">126.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">125.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>7.4</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>7.4</i></span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C61</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H20</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">127.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">127.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.4</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C12</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">128.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">129.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">8.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">8.2</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>H4<span class="sup"><sup><span class="it"><i>e</i></span></sup></span></i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">128.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">129.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>8.5</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>8.2</i></span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C60</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H19</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">129.3</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">130.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.3</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.8</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">130.1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">131.1<span class="sup"><sup><span class="it"><i>d</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C59</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H18</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">131.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">131.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.7</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C10</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">132.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">133.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">5.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">6.2</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C11</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H3</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">139.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">136.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.7</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C57</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>H21, H17, H29</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">138.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">141.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>8.4, 9.7, 10.5</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>8.9</i></span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C3</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">139.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">141.4<span class="sup"><sup><span class="it"><i>d</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C63</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>H29</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">155.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">160.1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>10.5</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>9.1</i></span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C67</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>H26/H27/H28, H25</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">168.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">168.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>2.0, 3.4</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>2.8</i></span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C64</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>H22/H23/H24, H25</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">168.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">168.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>1.8, 3.4</i></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry"><span class="it"><i>2.8</i></span></span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">179.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">176.5<span class="sup"><sup><span class="it"><i>d</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">C8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">179.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">178.2<span class="sup"><sup><span class="it"><i>d</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">–</span></td> </tr> <tr><td colspan="6"><span class="font_size_2 tfnu"><a id="TABLE2_TFNU2"></a>Notes: (<span class="it"><i>a</i></span>) calculated isotropic chemical shifts are determined from calculated chemical shieldings according to <span class="symbol">δ</span><span class="inf"><sub>calc</sub></span> = <span class="symbol">σ</span><span class="inf"><sub>ref</sub></span> − <span class="symbol">σ</span><span class="inf"><sub>calc</sub></span>, where <span class="symbol">σ</span><span class="inf"><sub>ref</sub></span> equals 30.0 ppm for <span class="sup"><sup>1</sup></span>H and 163.2 ppm for <span class="sup"><sup>13</sup></span>C. (<span class="it"><i>b</i></span>) H-atom labels and calculated and experimental <span class="sup"><sup>1</sup></span>H chemical shifts are presented in normal font for direct one-bond C—H connectivities, while longer-range C⋯H proximities (corresponding to cross peaks observed in the <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C spectra presented in Figs. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>b</i></span> and 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>c</i></span>) are presented in italics. (<span class="it"><i>c</i></span>) For CH<span class="inf"><sub>3</sub></span> groups, the calculated <span class="sup"><sup>1</sup></span>H chemical shifts correspond to the average over the three H atoms. (<span class="it"><i>d</i></span>) Experimental chemical shifts taken from the <span class="sup"><sup>13</sup></span>C CP MAS spectrum (Fig. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>a</i></span>) since no cross peaks are observed in the <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C spectra presented in Figs. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>b</i></span>) and 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>). (<span class="it"><i>e</i></span>) Note that the C7—H1 and C6—H4 cross peaks due to longer-range C⋯H proximities cannot be distinguished from the C9—H1 and C12—H4 cross peaks due to one-bond C—H connectivities – in the stick spectrum in Fig. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>), open bars denote the calculated (GIPAW) C7 and C6 <span class="sup"><sup>13</sup></span>C chemical shifts. <br /></span> </td></tr></tbody> </table> </td> </tr> </tbody> </table> </div> <p>Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a> compares <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C correlation spectra recorded with three different CP contact times of 100 µs (Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>a</i></span>), 500 µs (Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>b</i></span>) and 1 ms (Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>c</i></span>); Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>a</i></span>) is a copy of Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>), but presented in the normal orientation, <span class="it"><i>i.e.</i></span> with the direct (<span class="sup"><sup>13</sup></span>C) dimension horizontal. It is evident that additional cross peaks are observed for longer CP contact times – these correspond to longer-range C⋯H proximities (see italics font in Table 2<a href="#TABLE2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>). Notably, cross peaks are observed at <span class="sup"><sup>13</sup></span>C chemical shifts of 141.5 (atom C57), 160.1 (atom C63) and 168.2 ppm (atoms C64 and C67); these all correspond to intra­molecular proximities within the di­thia­non mol­ecule, <span class="it"><i>i.e.</i></span> C57 with H17 (9.1 ppm, 2.16 Å), H21 (8.0 ppm, 2.16 Å) and H29 (9.1 ppm, 2.06 Å), C63 with H29 (9.1 ppm, 2.01 Å), C64 and C67 with H25 (4.0 ppm, 2.16 and 2.17 Å) and CH<span class="inf"><sub>3</sub></span> protons (1.9 and 2.0 ppm, nearest distance 2.14 Å). Of most inter­est is the (160.1 ppm, 9.1 ppm) cross peak, which thus enables the determination of the NH <span class="sup"><sup>1</sup></span>H chemical shift.</p><div class="fig"> <table cellpadding="5" class="fig" summary="Figure 4" width="100%"> <tbody> <tr> <td class="td_align_center width_20"> <a href="df3006fig4.html"><img alt="[Figure 4]" class="figlnkthm img_align_middle" src="df3006fig4thm.gif" /> <br /></a> </td> <td> <span class="font_size_3"><b><a href="df3006fig4.html" id="FIG4">Figure 4</a></b></span> <br /><span class="font_size_2 caption"><span class="sup"><sup>1</sup></span>H (500 MHz)–<span class="sup"><sup>13</sup></span>C HETCOR MAS (12.5 kHz) spectra of the DI–PM cocrystal recorded using FSLG <span class="sup"><sup>1</sup></span>H homonuclear decoupling (Bielecki <span class="it"><i>et al.</i></span>, 1989<a id="sourceBB8"></a><a href="#BB8"><img alt="[Bielecki, A., Kolbert, A. C. & Levitt, M. H. (1989). Chem. Phys. Lett. 155, 341-346.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Bielecki, A., Kolbert, A. C. & Levitt, M. H. (1989). Chem. Phys. Lett. 155, 341-346." /></a>) in <span class="it"><i>t</i></span><span class="inf"><sub>1</sub></span> with a CP transfer duration of (<span class="it"><i>a</i></span>) 100 µs, (<span class="it"><i>b</i></span>) 500 µs and (<span class="it"><i>c</i></span>) 1 ms. The spectrum in part (<span class="it"><i>a</i></span>) is repeated from Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>c</i></span>). 104 transients were co-added for each of (<span class="it"><i>b</i></span>) 128 or (<span class="it"><i>c</i></span>) 90 <span class="it"><i>t</i></span><span class="inf"><sub>1</sub></span> FIDs using a recycle delay of (<span class="it"><i>b</i></span>) 6 or (<span class="it"><i>c</i></span>) 5.5 s, corresponding to a total experimental time of (<span class="it"><i>b</i></span>) 22 or (<span class="it"><i>c</i></span>) 14 h. The scaling factor in <span class="it"><i>F</i></span><span class="inf"><sub>1</sub></span> was determined to be (<span class="it"><i>a</i></span>) and (<span class="it"><i>b</i></span>) 1.80 or (<span class="it"><i>c</i></span>) 1.73. The base contour level is at (<span class="it"><i>a</i></span>) 20, (<span class="it"><i>b</i></span>) 13 and (<span class="it"><i>c</i></span>) 25% of the maximum peak height. Red crosses correspond to GIPAW-calculated <span class="sup"><sup>1</sup></span>H and <span class="sup"><sup>13</sup></span>C chemical shifts (see Table 2<a href="#TABLE2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>) for (<span class="it"><i>a</i></span>) one-bond C—H bonds and (<span class="it"><i>b</i></span>) and (<span class="it"><i>c</i></span>) C⋯H proximities between (<span class="it"><i>b</i></span>) 1.2 and 2.2 Å, and (<span class="it"><i>c</i></span>) 2.2 and 3.0 Å.</span></td> </tr> </tbody> </table> </div> <p>With all the <span class="sup"><sup>1</sup></span>H chemical shifts assigned, let us re-examine the <span class="sup"><sup>1</sup></span>H DQ MAS spectrum in Fig. 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>b</i></span>). In such a spectrum, cross peaks are observed in the DQ dimension at the sum of the two single-quantum (SQ) frequencies if there is a close proximity (typically up to 3.5 Å; Brown, 2007<a id="sourceBB12"></a><a href="#BB12"><img alt="[Brown, S. P. (2007). Prog. Nucl. Magn. Reson. Spectrosc. 50, 199-251.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Brown, S. P. (2007). Prog. Nucl. Magn. Reson. Spectrosc. 50, 199-251." /></a>, 2012<a id="sourceBB13"></a><a href="#BB13"><img alt="[Brown, S. P. (2012). Solid State Nucl. Magn. Reson. 41, 1-27.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Brown, S. P. (2012). Solid State Nucl. Magn. Reson. 41, 1-27." /></a>) between the corresponding two H atoms (a full listing of H⋯H proximities under 3.5 Å for the DI–PM cocrystal is given in Table S1 of the <a href="//scripts.iucr.org/cgi-bin/sendsup?df3006"><span class="it"><i>Supporting information</i></span></a>). Consider the two lowest-ppm aromatic CH protons H25 (4.0 ppm) and H2 (6.2 ppm) for which distinct <span class="sup"><sup>1</sup></span>H resonances are resolved in the <span class="sup"><sup>1</sup></span>H SQ dimension. For H25, the only DQ peak is at 4.0 + 2.0 = 6.0 ppm with the CH<span class="inf"><sub>3</sub></span> protons, since H25 is sandwiched between two methyl-group substituents on the PM mol­ecule. For H2, there is a DQ peak at 6.2 + 7.5 = 13.7 ppm corresponding to the intra­molecular H⋯H proximity with the neighbouring H1 (7.4 ppm, 2.50 Å) and H3 (7.7 ppm, 2.47 Å) DI aromatic CH protons, as well as a DQ peak at 6.2 + 2.0 = 8.2 ppm due to inter­molecular proximities to the PM CH<span class="inf"><sub>3</sub></span> H atoms (H23, H24, H28 and H22 at 2.90, 3.03, 3.12 and 3.12 Å, respectively). Considering the high-ppm region, DQ cross peaks for the overlapping PI NH H29 (9.1 ppm) and aromatic CH H17 (9.1 ppm) resonances are observed at 9.1 + 7.7 = 16.8 ppm for intra­molecular H29⋯H21 (2.21 Å) and H17⋯H18 (2.50 Å) proximities, as well as at 9.1 + 2.0 = 11.1 ppm for inter­molecular proximities to PM methyl-group protons (closest distances of H17⋯H26 = 2.48 Å and H29⋯H24 = 2.64 Å). For the other overlapping CH aromatic resonances, cross peaks due to intra­molecular proximities with other CH aromatic resonances, as well as inter­molecular proximities to the methyl protons, are also observed.</p></div> <div class="sec2" id="DIVSEC3.4"> <h4><a id="SEC3.4"></a>3.4. Comparison of experimental and calculated <span class="sup"><sup>1</sup></span>H and <span class="sup"><sup>13</sup></span>C chemical shifts</h4> <p>In the <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C correlation spectra presented in Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>, red crosses correspond to calculated (GIPAW) <span class="sup"><sup>13</sup></span>C and <span class="sup"><sup>1</sup></span>H chemical shifts. Specifically, in Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>a</i></span>), red crosses correspond to direct C—H one-bond connectivities (C—H distances under 1.2 Å), while in Figs. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>b</i></span>) and 4(<span class="it"><i>c</i></span>), red crosses are presented for C—H proximities between 1.2 and 2.2 Å (Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>b</i></span>), and between 2.2 and 3.0 Å (Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>c</i></span>). We comment here on the level of agreement between experimental and calculated (GIPAW) chemical shifts. Starting with a consideration of the aromatic CH moieties (see Fig. 4<a href="#FIG4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>a</i></span> and Table 2<a href="#TABLE2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>), the discrepancy between experiment and calculation is within 2 ppm for the <span class="sup"><sup>13</sup></span>C chemical shifts (except for C11, where the difference is 2.4 ppm); this corresponds to the established observation that the discrepancy is within 1% of the <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> range (∼200 ppm for <span class="sup"><sup>13</sup></span>C chemical shifts of diamagnetic mol­ecules). For the <span class="sup"><sup>1</sup></span>H chemical shifts, while most are within the usual 0.3 ppm, some exhibit slightly larger discrepancies, notably 0.6 ppm for atoms H17 and H25.</p><p>For the two CH<span class="inf"><sub>3</sub></span> groups (see Figs. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a> and 3<a href="#FIG3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>a</i></span>, and Table 2<a href="#TABLE2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>), there is excellent agreement for the <span class="sup"><sup>1</sup></span>H chemical shifts (within 0.1 ppm), whereas the calculated <span class="sup"><sup>13</sup></span>C chemical shifts are both 8.5 ppm lower than the experimental values, although the experimental difference in <span class="sup"><sup>13</sup></span>C chemical shifts between atoms C65 and C68 of 1.8 ppm is reproduced by the calculation (difference of 1.9 ppm). The explanation for this is well known, namely, the gradient of a plot of experimental <span class="sup"><sup>13</sup></span>C chemical shifts against calculated shielding deviates slightly from −1 (Harris <span class="it"><i>et al.</i></span>, 2007<a id="sourceBB24"></a><a href="#BB24"><img alt="[Harris, R. K., Hodgkinson, P., Pickard, C. J., Yates, J. R. & Zorin, V. (2007). Magn. Reson. Chem. 45, S174-S186.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Harris, R. K., Hodgkinson, P., Pickard, C. J., Yates, J. R. & Zorin, V. (2007). Magn. Reson. Chem. 45, S174-S186." /></a>; Ashbrook & McKay, 2016<a id="sourceBB4"></a><a href="#BB4"><img alt="[Ashbrook, S. E. & McKay, D. (2016). Chem. Commun. 52, 7186-7204.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Ashbrook, S. E. & McKay, D. (2016). Chem. Commun. 52, 7186-7204." /></a>), such that calculated <span class="sup"><sup>13</sup></span>C chemical shifts are too low and too high compared to experiment for low-ppm and high-ppm resonances if, as here (see Fig. 2<a href="#FIG2"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>), the gradient is constrained to −1 and a single reference shielding is used. An alternative approach would be to use different reference shieldings for different regions of the spectrum (Webber, Emsley <span class="it"><i>et al.</i></span>, 2010<a id="sourceBB53"></a><a href="#BB53"><img alt="[Webber, A. L., Emsley, L., Claramunt, R. M. & Brown, S. P. (2010). J. Phys. Chem. A, 114, 10435-10442.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Webber, A. L., Emsley, L., Claramunt, R. M. & Brown, S. P. (2010). J. Phys. Chem. A, 114, 10435-10442." /></a>).</p><p>Returning to the <span class="sup"><sup>1</sup></span>H chemical shifts, the biggest discrepancy is for the NH proton (H29), where the calculated <span class="sup"><sup>1</sup></span>H <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> of 10.5 ppm is 1.4 ppm higher than the experimental value of 9.1 ppm. Such a large difference is explained by a known temperature dependence (the experimental <span class="sup"><sup>1</sup></span>H <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> increases upon reducing the temperature) for hydrogen-bonded protons (Brown <span class="it"><i>et al.</i></span>, 2001<a id="sourceBB14"></a><a href="#BB14"><img alt="[Brown, S. P., Zhu, X. X., Saalwachter, K. & Spiess, H. W. (2001). J. Am. Chem. Soc. 123, 4275-4285.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Brown, S. P., Zhu, X. X., Saalwachter, K. & Spiess, H. W. (2001). J. Am. Chem. Soc. 123, 4275-4285." /></a>; Pickard <span class="it"><i>et al.</i></span>, 2007<a id="sourceBB39"></a><a href="#BB39"><img alt="[Pickard, C. J., Salager, E., Pintacuda, G., Elena, B. & Emsley, L. (2007). J. Am. Chem. Soc. 129, 8932-8933.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Pickard, C. J., Salager, E., Pintacuda, G., Elena, B. & Emsley, L. (2007). J. Am. Chem. Soc. 129, 8932-8933." /></a>; Webber, Elena <span class="it"><i>et al.</i></span>, 2010<a id="sourceBB52"></a><a href="#BB52"><img alt="[Webber, A. L., Elena, B., Griffin, J. M., Yates, J. R., Pham, T. N., Mauri, F., Pickard, C. J., Gil, A. M., Stein, R., Lesage, A., Emsley, L. & Brown, S. P. (2010). Phys. Chem. Chem. Phys. 12, 6970-6983.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Webber, A. L., Elena, B., Griffin, J. M., Yates, J. R., Pham, T. N., Mauri, F., Pickard, C. J., Gil, A. M., Stein, R., Lesage, A., Emsley, L. & Brown, S. P. (2010). Phys. Chem. Chem. Phys. 12, 6970-6983." /></a>), considering that the calculation corresponds to 0 K.</p></div> <div class="sec2" id="DIVSEC3.5"> <h4><a id="SEC3.5"></a>3.5. Calculated mol­ecule-to-crystal changes in chemical shifts</h4> <p>For cases such as the DI–PM cocrystal in this article, an NMR crystallography study is able to provide new insight by means of a comparison of chemical shifts calculated for the full <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure</a> with those calculated for an isolated mol­ecule (as extracted from the geometry-optimized crystal structure) (Yates <span class="it"><i>et al.</i></span>, 2005<a id="sourceBB54"></a><a href="#BB54"><img alt="[Yates, J. R., Pham, T. N., Pickard, C. J., Mauri, F., Amado, A. M., Gil, A. M. & Brown, S. P. (2005). J. Am. Chem. Soc. 127, 10216-10220.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Yates, J. R., Pham, T. N., Pickard, C. J., Mauri, F., Amado, A. M., Gil, A. M. & Brown, S. P. (2005). J. Am. Chem. Soc. 127, 10216-10220." /></a>; Schmidt <span class="it"><i>et al.</i></span>, 2006<a id="sourceBB42"></a><a href="#BB42"><img alt="[Schmidt, J., Hoffmann, A., Spiess, H. W. & Sebastiani, D. (2006). J. Phys. Chem. B, 110, 23204-23210.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Schmidt, J., Hoffmann, A., Spiess, H. W. & Sebastiani, D. (2006). J. Phys. Chem. B, 110, 23204-23210." /></a>; Mafra <span class="it"><i>et al.</i></span>, 2012<a id="sourceBB33"></a><a href="#BB33"><img alt="[Mafra, L., Santos, S. M., Siegel, R., Alves, I., Paz, F. A. A., Dudenko, D. & Spiess, H. W. (2012). J. Am. Chem. Soc. 134, 71-74.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Mafra, L., Santos, S. M., Siegel, R., Alves, I., Paz, F. A. A., Dudenko, D. & Spiess, H. W. (2012). J. Am. Chem. Soc. 134, 71-74." /></a>). Specifically, a mol­ecule-to-crystal difference in <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> is indicative of a combination of inter­molecular inter­actions, notably hydrogen bonding and ring currents due to C—H⋯<span class="symbol">π</span> inter­actions, whereby the latter can be separately qu­anti­fied by means of the nucleus independent <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> (NICS) (von Ragué Schleyer <span class="it"><i>et al.</i></span>, 1996<a id="sourceBB40"></a><a href="#BB40"><img alt="[Ragué Schleyer, P. von, Maerker, C., Dransfeld, A., Jiao, H. & van Eikema Hommes, N. J. R. (1996). J. Am. Chem. Soc. 118, 6317-6318.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Ragué Schleyer, P. von, Maerker, C., Dransfeld, A., Jiao, H. & van Eikema Hommes, N. J. R. (1996). J. Am. Chem. Soc. 118, 6317-6318." /></a>; Sebastiani, 2006<a id="sourceBB44"></a><a href="#BB44"><img alt="[Sebastiani, D. (2006). ChemPhysChem, 7, 164-175.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Sebastiani, D. (2006). ChemPhysChem, 7, 164-175." /></a>; Uldry <span class="it"><i>et al.</i></span>, 2008<a id="sourceBB49"></a><a href="#BB49"><img alt="[Uldry, A. C., Griffin, J. M., Yates, J. R., Perez-Torralba, M., Maria, M. D. S., Webber, A. L., Beaumont, M. L. L., Samoson, A., Claramunt, R. M., Pickard, C. J. & Brown, S. P. (2008). J. Am. Chem. Soc. 130, 945-954.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Uldry, A. C., Griffin, J. M., Yates, J. R., Perez-Torralba, M., Maria, M. D. S., Webber, A. L., Beaumont, M. L. L., Samoson, A., Claramunt, R. M., Pickard, C. J. & Brown, S. P. (2008). J. Am. Chem. Soc. 130, 945-954." /></a>; Mafra <span class="it"><i>et al.</i></span>, 2012<a href="#BB33"><img alt="[Mafra, L., Santos, S. M., Siegel, R., Alves, I., Paz, F. A. A., Dudenko, D. & Spiess, H. W. (2012). J. Am. Chem. Soc. 134, 71-74.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Mafra, L., Santos, S. M., Siegel, R., Alves, I., Paz, F. A. A., Dudenko, D. & Spiess, H. W. (2012). J. Am. Chem. Soc. 134, 71-74." /></a>). Consider Table 3<a href="#TABLE3"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>, which presents the change in <span class="sup"><sup>1</sup></span>H <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> upon going from an isolated mol­ecule to the full crystal, <span class="symbol">Δ</span><span class="symbol">δ</span><span class="inf"><sub>crystal–mol­ecule</sub></span>, for the different H atoms in the DI–PM cocrystal. The largest positive change of 3.6 ppm is observed for the NH (H29) atom that is involved in an inter­molecular N—H⋯O hydrogen bond to atom O1 (see Fig. 1<a href="#FIG1"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a><span class="it"><i>a</i></span>; the N⋯O and H⋯O distances are 2.95 and 1.96 Å, respectively, with a 162° N—H⋯O angle). Inter­estingly, <span class="symbol">Δ</span><span class="symbol">δ</span><span class="inf"><sub>crystal–mol­ecule</sub></span> = 2.0 ppm for the aromatic CH H21 atom, for which Fig. 1<a href="#FIG1"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>(<span class="it"><i>a</i></span>) identifies an inter­molecular C—H⋯O so-called weak hydrogen-bonding (Desiraju & Steiner, 1999<a id="sourceBB18"></a><a href="#BB18"><img alt="[Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford University Press.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford University Press." /></a>; Yates <span class="it"><i>et al.</i></span>, 2005<a href="#BB54"><img alt="[Yates, J. R., Pham, T. N., Pickard, C. J., Mauri, F., Amado, A. M., Gil, A. M. & Brown, S. P. (2005). J. Am. Chem. Soc. 127, 10216-10220.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Yates, J. R., Pham, T. N., Pickard, C. J., Mauri, F., Amado, A. M., Gil, A. M. & Brown, S. P. (2005). J. Am. Chem. Soc. 127, 10216-10220." /></a>; Uldry <span class="it"><i>et al.</i></span>, 2008<a href="#BB49"><img alt="[Uldry, A. C., Griffin, J. M., Yates, J. R., Perez-Torralba, M., Maria, M. D. S., Webber, A. L., Beaumont, M. L. L., Samoson, A., Claramunt, R. M., Pickard, C. J. & Brown, S. P. (2008). J. Am. Chem. Soc. 130, 945-954.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Uldry, A. C., Griffin, J. M., Yates, J. R., Perez-Torralba, M., Maria, M. D. S., Webber, A. L., Beaumont, M. L. L., Samoson, A., Claramunt, R. M., Pickard, C. J. & Brown, S. P. (2008). J. Am. Chem. Soc. 130, 945-954." /></a>) inter­action (the C⋯O and H⋯O distances are 3.24 and 2.35 Å, respectively, with a 138° C—H⋯O angle). The other H atoms, for which the magnitude of <span class="symbol">Δ</span><span class="symbol">δ</span><span class="inf"><sub>crystal–mol­ecule</sub></span> exceeds 1 ppm, are H25 (−2.7 ppm) and H2 (−1.6 ppm); as shown in Fig. 5<a href="#FIG5"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>, these marked changes in the <span class="sup"><sup>1</sup></span>H <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> are a consequence of ring current effects associated with the proton pointing towards the centre of a six-membered aromatic ring of a nearby PM mol­ecule in a C—H⋯<span class="symbol">π</span> inter­action, as has been noted previously in a number of other cases (Brouwer <span class="it"><i>et al.</i></span>, 2008<a id="sourceBB11"></a><a href="#BB11"><img alt="[Brouwer, D. H., Alavi, S. & Ripmeester, J. A. (2008). Phys. Chem. Chem. Phys. 10, 3857-3860.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Brouwer, D. H., Alavi, S. & Ripmeester, J. A. (2008). Phys. Chem. Chem. Phys. 10, 3857-3860." /></a>; Mafra <span class="it"><i>et al.</i></span>, 2012<a href="#BB33"><img alt="[Mafra, L., Santos, S. M., Siegel, R., Alves, I., Paz, F. A. A., Dudenko, D. & Spiess, H. W. (2012). J. Am. Chem. Soc. 134, 71-74.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Mafra, L., Santos, S. M., Siegel, R., Alves, I., Paz, F. A. A., Dudenko, D. & Spiess, H. W. (2012). J. Am. Chem. Soc. 134, 71-74." /></a>; Brown, 2012<a href="#BB13"><img alt="[Brown, S. P. (2012). Solid State Nucl. Magn. Reson. 41, 1-27.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Brown, S. P. (2012). Solid State Nucl. Magn. Reson. 41, 1-27." /></a>).</p><div class="table"> <table cellpadding="2" class="bgcolor_FFCCCC" summary="Comparison of experimental 1H chemical shifts with calculateda (GIPAW) values (all in ppm) for the DI–PM cocrystal for the full crystal structure and an isolated di­thia­non or pyrimethanil mol­ecule" width="100%"> <tbody> <tr> <td> <table class="bgcolor_FFCCCC tbheader" summary="Comparison of experimental 1H chemical shifts with calculateda (GIPAW) values (all in ppm) for the DI–PM cocrystal for the full crystal structure and an isolated di­thia­non or pyrimethanil mol­ecule" width="100%"> <tbody> <tr> <td align="left" class="bgcolor_FFCCCC" valign="bottom"> <p><span class="font_size_3 table_number"><b><a id="TABLE3">Table 3</a></b></span><br /><span class="font_size_2 tbcaption">Comparison of experimental <span class="sup"><sup>1</sup></span>H chemical shifts with calculated<span class="sup"><sup><span class="it"><i>a</i></span></sup></span> (GIPAW) values (all in ppm) for the DI–PM cocrystal for the full <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure</a> and an isolated di­thia­non or pyrimethanil mol­ecule</span> </p></td> </tr> </tbody> </table> <table class="bgcolor_FFCCCC tbheader" summary="Comparison of experimental 1H chemical shifts with calculateda (GIPAW) values (all in ppm) for the DI–PM cocrystal for the full crystal structure and an isolated di­thia­non or pyrimethanil mol­ecule" width="100%"> <tbody> <tr> <td align="left" class="bgcolor_FFCCCC" valign="bottom"> </td> </tr> </tbody> </table> <table summary="Comparison of experimental 1H chemical shifts with calculateda (GIPAW) values (all in ppm) for the DI–PM cocrystal for the full crystal structure and an isolated di­thia­non or pyrimethanil mol­ecule" width="100%"> <thead valign="bottom"> <tr> <th align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="bottom"><span class="font_size_2">Atom</span></th> <th align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="bottom"><span class="font_size_2"><span class="symbol">δ</span><span class="inf"><sub>exp </sub></span></span></th> <th align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="bottom"><span class="font_size_2"><span class="symbol">δ</span><span class="inf"><sub>crystal</sub></span></span></th> <th align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="bottom"><span class="font_size_2"><span class="symbol">δ</span><span class="inf"><sub>mol­ecule</sub></span></span></th> <th align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="bottom"><span class="font_size_2"><span class="symbol">Δ</span><span class="symbol">δ</span><span class="inf"><sub>crystal–mol­ecule</sub></span></span></th> </tr> </thead> <tbody valign="top"> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−0.4</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">6.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">5.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−1.5</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H3</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.2</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">8.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">8.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.7</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H17</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">9.1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">9.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">9.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.5</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H18</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.0</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.7</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H19</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.3</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">6.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.7</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H20</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">7.0</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.6</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H21</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">8.0</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">8.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">6.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">2.0</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H22/23/24<span class="sup"><sup><span class="it"><i>b</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">1.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">1.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">1.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−0.1</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H25</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">4.0</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">3.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">6.1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−2.7</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H26/27/28<span class="sup"><sup><span class="it"><i>b</i></span></sup></span></span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">2.0</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">2.0</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">1.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">0.2</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">H29</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">9.1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">10.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">6.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">3.6</span></td> </tr> <tr><td colspan="5"><span class="font_size_2 tfnu"><a id="TABLE3_TFNU3"></a>Notes: (<span class="it"><i>a</i></span>) calculated isotropic chemical shieldings are determined from calculated chemical shieldings according to <span class="symbol">δ</span><span class="inf"><sub>calc</sub></span> = <span class="symbol">σ</span><span class="inf"><sub>ref</sub></span> − <span class="symbol">σ</span><span class="inf"><sub>calc</sub></span>, where <span class="symbol">σ</span><span class="inf"><sub>ref</sub></span> equals 30.0 ppm; (<span class="it"><i>b</i></span>) for CH<span class="inf"><sub>3</sub></span> groups, the calculated <span class="sup"><sup>1</sup></span>H chemical shifts correspond to the average over the three H atoms. <br /></span> </td></tr></tbody> </table> </td> </tr> </tbody> </table> </div> <div class="fig"> <table cellpadding="5" class="fig" summary="Figure 5" width="100%"> <tbody> <tr> <td class="td_align_center width_20"> <a href="df3006fig5.html"><img alt="[Figure 5]" class="figlnkthm img_align_middle" src="df3006fig5thm.gif" /> <br /></a> </td> <td> <span class="font_size_3"><b><a href="df3006fig5.html" id="FIG5">Figure 5</a></b></span> <br /><span class="font_size_2 caption">Schematic representations showing C—H⋯<span class="symbol">π</span> inter­actions for aromatic atoms (<span class="it"><i>a</i></span>) H25 and (<span class="it"><i>b</i></span>) H2.</span></td> </tr> </tbody> </table> </div> <p>In the above discussion in §3.1<a href="#SEC3.1"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>, a close S⋯O distance, equal to 3.10 Å, between the O2 and S2 atoms of neighbouring DI mol­ecules was noted; this is less than the sum of the van der Waals radii (3.32 Å) (Beno <span class="it"><i>et al.</i></span>, 2015<a id="sourceBB5"></a><a href="#BB5"><img alt="[Beno, B. R., Yeung, K. S., Bartberger, M. D., Pennington, L. D. & Meanwell, N. A. (2015). J. Med. Chem. 58, 4383-4438.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Beno, B. R., Yeung, K. S., Bartberger, M. D., Pennington, L. D. & Meanwell, N. A. (2015). J. Med. Chem. 58, 4383-4438." /></a>; Zhang <span class="it"><i>et al.</i></span>, 2015<a id="sourceBB56"></a><a href="#BB56"><img alt="[Zhang, X., Gong, Z., Li, J. & Lu, T. (2015). J. Chem. Inf. Model. 55, 2138-2153.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Zhang, X., Gong, Z., Li, J. & Lu, T. (2015). J. Chem. Inf. Model. 55, 2138-2153." /></a>). Indeed, there is a growing literature discussing S⋯O inter­actions (Burling & Goldstein, 1992<a href="#BB15"><img alt="[Burling, F. T. & Goldstein, B. M. (1992). J. Am. Chem. Soc. 114, 2313-2320.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Burling, F. T. & Goldstein, B. M. (1992). J. Am. Chem. Soc. 114, 2313-2320." /></a>; Iwaoka <span class="it"><i>et al.</i></span>, 2002<a id="sourceBB27"></a><a href="#BB27"><img alt="[Iwaoka, M., Takemoto, S. & Tomoda, S. (2002). J. Am. Chem. Soc. 124, 10613-10620.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Iwaoka, M., Takemoto, S. & Tomoda, S. (2002). J. Am. Chem. Soc. 124, 10613-10620." /></a>; Beno <span class="it"><i>et al.</i></span>, 2015<a href="#BB5"><img alt="[Beno, B. R., Yeung, K. S., Bartberger, M. D., Pennington, L. D. & Meanwell, N. A. (2015). J. Med. Chem. 58, 4383-4438.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Beno, B. R., Yeung, K. S., Bartberger, M. D., Pennington, L. D. & Meanwell, N. A. (2015). J. Med. Chem. 58, 4383-4438." /></a>). While we have not carried out <span class="sup"><sup>17</sup></span>O or <span class="sup"><sup>33</sup></span>S solid-state NMR experiments as part of this study, an NMR crystallography approach enables the effect of such a putative S⋯O inter­action on the oxygen and sulfur NMR chemical shieldings to be investigated by means of the GIPAW calculation that reports on all nuclei in the solid-state structure. An inspection of Table 4<a href="#TABLE4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a> shows that it is inter­esting that <span class="symbol">Δ</span><span class="symbol">δ</span><span class="inf"><sub>crystal–mol­ecule</sub></span> (note that this is the negative of the difference in calculated absolute shielding, with the latter being stated in Table 4<a href="#TABLE4"><img alt="[link]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" /></a>) is much larger for O1 (−98 ppm), which is involved in a N—H⋯O inter­molecular hydrogen bonding, as compared to that for O2 (−23 ppm). Moreover, the change for S2 (13 ppm) is less than that for S1 (25 ppm), with both changes being small, though there is limited information on the range of experimentally observed solid-state NMR <span class="sup"><sup>33</sup></span>S chemical shifts (Hansen <span class="it"><i>et al.</i></span>, 2008<a id="sourceBB22"></a><a href="#BB22"><img alt="[Hansen, M. R., Brorson, M., Bildsoe, H., Skibsted, J. & Jakobsen, H. J. (2008). J. Magn. Reson. 190, 316-326.]" class="linkarrow img_align_bottom img_border_0" src="../../../../../../logos/arrows/c_arr.gif" title="Hansen, M. R., Brorson, M., Bildsoe, H., Skibsted, J. & Jakobsen, H. J. (2008). J. Magn. Reson. 190, 316-326." /></a>). We conclude that even though there is a close inter­molecular S⋯O distance of 3.10 Å in the DI–PM cocrystal, there is not a marked effect on the calculated NMR chemical shieldings for the O2 and S2 nuclei.</p><div class="table"> <table cellpadding="2" class="bgcolor_FFCCCC" summary="Comparison of calculated (GIPAW) NMR chemical shieldings (in ppm) for the DI–PM cocrystal for the full crystal structure and an isolated di­thia­non or pyrimethanil mol­ecule" width="100%"> <tbody> <tr> <td> <table class="bgcolor_FFCCCC tbheader" summary="Comparison of calculated (GIPAW) NMR chemical shieldings (in ppm) for the DI–PM cocrystal for the full crystal structure and an isolated di­thia­non or pyrimethanil mol­ecule" width="100%"> <tbody> <tr> <td align="left" class="bgcolor_FFCCCC" valign="bottom"> <p><span class="font_size_3 table_number"><b><a id="TABLE4">Table 4</a></b></span><br /><span class="font_size_2 tbcaption">Comparison of calculated (GIPAW) NMR chemical shieldings (in ppm) for the DI–PM cocrystal for the full <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure</a> and an isolated di­thia­non or pyrimethanil mol­ecule</span> </p></td> </tr> </tbody> </table> <table class="bgcolor_FFCCCC tbheader" summary="Comparison of calculated (GIPAW) NMR chemical shieldings (in ppm) for the DI–PM cocrystal for the full crystal structure and an isolated di­thia­non or pyrimethanil mol­ecule" width="100%"> <tbody> <tr> <td align="left" class="bgcolor_FFCCCC" valign="bottom"> </td> </tr> </tbody> </table> <table summary="Comparison of calculated (GIPAW) NMR chemical shieldings (in ppm) for the DI–PM cocrystal for the full crystal structure and an isolated di­thia­non or pyrimethanil mol­ecule" width="100%"> <thead valign="bottom"> <tr> <th align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="bottom"><span class="font_size_2">Atom</span></th> <th align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="bottom"><span class="font_size_2"><span class="symbol">σ</span><span class="inf"><sub>mol­ecule</sub></span></span></th> <th align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="bottom"><span class="font_size_2"><span class="symbol">σ</span><span class="inf"><sub>crystal</sub></span></span></th> <th align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="bottom"><span class="font_size_2"><span class="symbol">σ</span><span class="inf"><sub>crystal–mol­ecule</sub></span></span></th> </tr> </thead> <tbody valign="top"> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">N1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−106.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−88.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">17.5</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">N2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−107.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−88.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">18.3</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">N9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">98.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">91.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−7.4</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">N10</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−30.1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−33.0</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−2.9</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">N11</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−44.5</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−42.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">2.1</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">O1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−363.4</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−265.9</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">97.5</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">O2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−345.3</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−322.2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">23.1</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">S1</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">330.7</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">305.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−25.1</span></td> </tr> <tr> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">S2</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">333.8</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">320.6</span></td> <td align="left" class="bgcolor_FFFFFF" colspan="1" rowspan="1" valign="top"><span class="font_size_2 table_entry">−13.2</span></td> </tr> <tr><td colspan="4"></td></tr></tbody> </table> </td> </tr> </tbody> </table> </div> </div> </div> <div class="sec1" id="DIVSEC4"> <h3><a id="SEC4"></a>4. Summary</h3> <p>In summary, we have presented here an NMR crystallography study of an agrochemical cocrystal. Specifically in combination with a GIPAW calculation of the NMR shieldings, <span class="sup"><sup>1</sup></span>H–<span class="sup"><sup>13</sup></span>C 2D correlation spectra enable the resolution and assignment of the NH, aromatic CH and methyl resonances for the DI–PM cocrystal, while specific intra- and inter­molecular H⋯H proximities are identified in a <span class="sup"><sup>1</sup></span>H DQ MAS spectrum. The performing of separate GIPAW calculations for the full <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure</a> and isolated DI and PM mol­ecules yields the change in the NMR <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> upon going from the mol­ecule to the <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure,</a> thus allowing the qu­anti­tation of specific N—H⋯O, C—H⋯O and C—H⋯<span class="symbol">π</span> inter­actions.</p></div> <div class="supmat"> <a id="suppinfoanchor"></a> <h3 id="suppinfo">Supporting information</h3> <!-- supmat links inside this --> <div class="art_codelinks"> <div class="art_codelinks_csd"><p> <span class="art_codelinks_head">CCDC reference: </span><a href="//scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1507863">1507863</a></p></div> </div> <div class="file_links_other"> <p><a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">Crystal structure:</a> contains datablocks global, I. DOI: <a href="https://doi.org/10.1107/S2053229617000870/df3006sup1.cif">https://doi.org/10.1107/S2053229617000870/df3006sup1.cif</a></p> <p>Structure factors: contains datablock I. DOI: <a href="https://doi.org/10.1107/S2053229617000870/df3006Isup3.hkl">https://doi.org/10.1107/S2053229617000870/df3006Isup3.hkl</a></p> <p>CASTEP <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/CIF' onclick="return makeSubWindow("https://dictionary.iucr.org/CIF", 'Navigator')">cif</a> output. DOI: <a href="https://doi.org/10.1107/S2053229617000870/df3006sup2.txt">https://doi.org/10.1107/S2053229617000870/df3006sup2.txt</a></p> <p>magres file. DOI: <a href="https://doi.org/10.1107/S2053229617000870/df3006sup4.txt">https://doi.org/10.1107/S2053229617000870/df3006sup4.txt</a></p> <p>Additional Tables (DQ NMR data and distances as well as a comparison of experimental and calculated (GIPAW) 13C <a target='Navigator' class="ref_lookup_orange hideorange" href='https://goldbook.iupac.org/C01036.html' onclick="return makeSubWindow("https://goldbook.iupac.org/C01036.html", 'Navigator')">chemical shift</a> values) and a Figure showing the difference in the numbering schemes between the crystallographic data and the output of the GIPAW (CASTEP) calculations. DOI: <a href="https://doi.org/10.1107/S2053229617000870/df3006sup5.pdf">https://doi.org/10.1107/S2053229617000870/df3006sup5.pdf</a></p> </div> <br /> <!-- /supmat links inside this --> <div class="sup_rescomm sup_e" id="sup_imported"> <div class="computingdetails"> <a name="computingdetails"></a> <div class="heading2"> Computing details <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> </div> <!-- endheading2div --><p>Data collection: <i>CrysAlis PRO</i> (Agilent, 2014); cell <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Refinement' onclick="return makeSubWindow("https://dictionary.iucr.org/Refinement", 'Navigator')">refinement:</a> <i>CrysAlis PRO</i> (Agilent, 2014); data reduction: <i>CrysAlis PRO</i> (Agilent, 2014); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: <i>CRYSTALS</i> (Betteridge <i>et al.</i>, 2003); molecular graphics: <i>CAMERON</i> (Watkin <i>et al.</i>, 1996) and <i>Mercury</i> (Macrae <i>et al.</i>, 2006); software used to prepare material for publication: <i>CRYSTALS</i> (Betteridge <i>et al.</i>, 2003).</p> </div> <!-- endcomputingdetailsdiv --> <div class="datablock1"> <!-- datablocklabel --> <div class="actac_oldstyle"> <div class="heading2"> <a name="chemicalname1"></a>5,10-Dioxo-5<i>H</i>,10<i>H</i>-naphtho[2,3-<i>b</i>][1,4]dithiine-2,3-dicarbonitrile–4,6-dimethyl-<i>N</i>-phenylpyrimidin-2-amine (1/1) <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> </div> <!-- endheading2div --> </div> <!-- enddatablocklabel --> <div class="tablewrapcrystaldatalong"> <span class="heading3">Crystal data</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table class="tabledata" style="table-layout:fixed" summary="" width="80%"> <colgroup span="2"> <col width="50%" /> <col width="50%" /> </colgroup> <tr><td class="tabledata" width="50%">C<sub>14</sub>H<sub>4</sub>N<sub>2</sub>O<sub>2</sub>S<sub>2</sub>·C<sub>12</sub>H<sub>13</sub>N<sub>3</sub></td><td class="tabledata" width="50%"><i>F</i>(000) = 1024</td></tr><tr><td class="tabledata" width="50%"><i>M</i><i><sub>r</sub></i> = 495.59</td><td class="tabledata" width="50%"><i>D</i><sub>x</sub> = 1.467 Mg m<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td class="tabledata" width="50%">Monoclinic, <i>P</i>2<sub>1</sub>/<i>n</i></td><td class="tabledata" width="50%">Cu <i>K</i><span style="font-family:Times">α</span> radiation, <span style="font-family:Times">λ</span> = 1.54184 Å</td></tr><tr><td class="tabledata" width="50%">Hall symbol: -P 2yn</td><td class="tabledata" width="50%">Cell parameters from 2711 reflections</td></tr><tr><td class="tabledata" width="50%"><i>a</i> = 7.1707 (2) Å</td><td class="tabledata" width="50%"><span style="font-family:Times">θ</span> = 5.0–62.6°</td></tr><tr><td class="tabledata" width="50%"><i>b</i> = 22.8006 (6) Å</td><td class="tabledata" width="50%">µ = 2.45 mm<span style="font-family:Times"><sup>−</sup></span><sup>1</sup></td></tr><tr><td class="tabledata" width="50%"><i>c</i> = 13.8237 (4) Å</td><td class="tabledata" width="50%"><i>T</i> = 100 K</td></tr><tr><td class="tabledata" width="50%"><span style="font-family:Times">β</span> = 97.047 (3)°</td><td class="tabledata" width="50%">Plate, purple</td></tr><tr><td class="tabledata" width="50%"><i>V</i> = 2243.04 (7) Å<sup>3</sup></td><td class="tabledata" width="50%">0.60 × 0.10 × 0.02 mm</td></tr><tr><td class="tabledata" width="50%"><i>Z</i> = 4</td><td class="tabledata" width="50%"></td></tr></table><!-- endtabledatatable --> </div> <!-- endtablewrapcrystaldatalongdiv --> <div class="tablewrapdatacollectionlong"> <span class="heading3">Data collection</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table class="tabledata" style="table-layout:fixed" summary="" width="80%"> <colgroup span="2"> <col width="50%" /> <col width="50%" /> </colgroup> <tr><td class="tabledata" width="50%">Agilent Xcalibur Onyx Ultra <br />diffractometer</td><td class="tabledata" width="50%">2667 reflections with <i>I</i> > 2.0<span style="font-family:Times">σ</span>(<i>I</i>)</td></tr><tr><td class="tabledata" width="50%">Mirror monochromator</td><td class="tabledata" width="50%"><i>R</i><sub>int</sub> = 0.035</td></tr><tr><td class="tabledata" width="50%"><span style="font-family:Times">ω</span>/2<span style="font-family:Times">θ</span> scans</td><td class="tabledata" width="50%"><span style="font-family:Times">θ</span><sub>max</sub> = 58.9°, <span style="font-family:Times">θ</span><sub>min</sub> = 3.2°</td></tr><tr><td class="tabledata" width="50%">Absorption correction: multi-scan <br />(CrysAlis PRO; Agilent, 2014)</td><td class="tabledata" width="50%"><i>h</i> = <span style="font-family:Times">−</span>5<span style="font-family:Times">→</span>7</td></tr><tr><td class="tabledata" width="50%"><i>T</i><sub>min</sub> = 0.596, <i>T</i><sub>max</sub> = 1.000</td><td class="tabledata" width="50%"><i>k</i> = <span style="font-family:Times">−</span>25<span style="font-family:Times">→</span>25</td></tr><tr><td class="tabledata" width="50%">5143 measured reflections</td><td class="tabledata" width="50%"><i>l</i> = <span style="font-family:Times">−</span>14<span style="font-family:Times">→</span>15</td></tr><tr><td class="tabledata" width="50%">3160 independent reflections</td><td class="tabledata" width="50%"></td></tr></table><!-- endtabledatatable --> </div> <!-- endtablewrapdatacollectionlongdiv --> <div class="tablewraprefinementdatalong"> <a name="refinementdata1"></a><span class="heading3">Refinement</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table class="tabledata" style="table-layout:fixed" summary="" width="80%"> <colgroup span="2"> <col width="50%" /> <col width="50%" /> </colgroup> <tr><td class="tabledata" width="50%">Refinement on <i>F</i><sup>2</sup></td><td class="tabledata" width="50%">Primary atom site location: other</td></tr><tr><td class="tabledata" width="50%">Least-squares matrix: full</td><td class="tabledata" width="50%">Hydrogen site location: difference Fourier map</td></tr><tr><td class="tabledata" width="50%"><i>R</i>[<i>F</i><sup>2</sup> > 2<span style="font-family:Times">σ</span>(<i>F</i><sup>2</sup>)] = 0.045</td><td class="tabledata" width="50%">H atoms treated by a mixture of independent and constrained refinement</td></tr><tr><td class="tabledata" width="50%"><i>wR</i>(<i>F</i><sup>2</sup>) = 0.094</td><td class="tabledata" width="50%"> Method, part 1, Chebychev polynomial [<i>w</i>eight] = 1.0/[A<sub>0</sub>*T<sub>0</sub>(x) + A<sub>1</sub>*T<sub>1</sub>(x) ··· + A<sub>n-1</sub>]*T<sub>n-1</sub>(x)] <br />where A<sub>i</sub> are the Chebychev coefficients listed belo<i>w</i> and x = <i>F</i> /<i>F</i>max Method = Robust Weighting W = [<i>w</i>eight] * [1-(delta<i>F</i>/6*sigma<i>F</i>)<sup>2</sup>]<sup>2</sup> A<sub>i</sub> are: 0.138E + 04 0.207E + 04 0.111E + 04 326.</td></tr><tr><td class="tabledata" width="50%"><i>S</i> = 0.98</td><td class="tabledata" width="50%">(Δ/<span style="font-family:Times">σ</span>)<sub>max</sub> = 0.001</td></tr><tr><td class="tabledata" width="50%">3141 reflections</td><td class="tabledata" width="50%">Δ<span style="font-family:Times">ρ</span><sub>max</sub> = 0.43 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td class="tabledata" width="50%">109 parameters</td><td class="tabledata" width="50%">Δ<span style="font-family:Times">ρ</span><sub>min</sub> = <span style="font-family:Times">−</span>0.37 e Å<span style="font-family:Times"><sup>−</sup></span><sup>3</sup></td></tr><tr><td class="tabledata" width="50%">3 restraints</td><td class="tabledata" width="50%"></td></tr></table><!-- endtabledatatable --> </div> <!-- endtablewraprefinementdatalongdiv --> <div class="specialdetails"> <div class="tablewrap"> <a name="specialdetails1"></a><span class="heading3">Special details</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --> <table class="tabledata" style="table-layout:fixed" width="100%"> <tr><td class="tabledata"><p><b>Experimental</b>. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. </p><p>Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.</p></td></tr></table> </div> </div> <!-- endspecialdetailsdiv --> <div class="tablewrapcoords"> <a name="fractionalatomiccoordinates1"></a> <span class="heading3">Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table class="tabledata" style="table-layout:fixed" summary="" width="100%"><tr><td class="tabledata"> </td><td class="tabledata"><i>x</i></td><td class="tabledata"><i>y</i></td><td class="tabledata"><i>z</i></td><td class="tabledata"><i>U</i><sub>iso</sub>*/<i>U</i><sub>eq</sub></td><td class="tabledata"></td></tr><tr><td class="tabledata">S1</td><td class="tabledata">0.57630 (11)</td><td class="tabledata">0.51819 (3)</td><td class="tabledata">0.79844 (6)</td><td class="tabledata">0.0223</td><td class="tabledata"></td></tr><tr><td class="tabledata">C2</td><td class="tabledata">0.3685 (4)</td><td class="tabledata">0.48079 (13)</td><td class="tabledata">0.7529 (2)</td><td class="tabledata">0.0212</td><td class="tabledata"></td></tr><tr><td class="tabledata">C3</td><td class="tabledata">0.2072 (4)</td><td class="tabledata">0.47646 (13)</td><td class="tabledata">0.7926 (2)</td><td class="tabledata">0.0202</td><td class="tabledata"></td></tr><tr><td class="tabledata">S4</td><td class="tabledata">0.14929 (11)</td><td class="tabledata">0.50645 (3)</td><td class="tabledata">0.90297 (5)</td><td class="tabledata">0.0206</td><td class="tabledata"></td></tr><tr><td class="tabledata">C5</td><td class="tabledata">0.3411 (4)</td><td class="tabledata">0.55384 (12)</td><td class="tabledata">0.9352 (2)</td><td class="tabledata">0.0177</td><td class="tabledata"></td></tr><tr><td class="tabledata">C6</td><td class="tabledata">0.5006 (4)</td><td class="tabledata">0.55878 (12)</td><td class="tabledata">0.8951 (2)</td><td class="tabledata">0.0175</td><td class="tabledata"></td></tr><tr><td class="tabledata">C7</td><td class="tabledata">0.6476 (4)</td><td class="tabledata">0.60247 (12)</td><td class="tabledata">0.9342 (2)</td><td class="tabledata">0.0179</td><td class="tabledata"></td></tr><tr><td class="tabledata">O8</td><td class="tabledata">0.7809 (3)</td><td class="tabledata">0.61031 (9)</td><td class="tabledata">0.88850 (15)</td><td class="tabledata">0.0221</td><td class="tabledata"></td></tr><tr><td class="tabledata">C9</td><td class="tabledata">0.6255 (4)</td><td class="tabledata">0.63243 (12)</td><td class="tabledata">1.0265 (2)</td><td class="tabledata">0.0167</td><td class="tabledata"></td></tr><tr><td class="tabledata">C10</td><td class="tabledata">0.4604 (4)</td><td class="tabledata">0.62563 (12)</td><td class="tabledata">1.0704 (2)</td><td class="tabledata">0.0176</td><td class="tabledata"></td></tr><tr><td class="tabledata">C11</td><td class="tabledata">0.3051 (4)</td><td class="tabledata">0.58862 (13)</td><td class="tabledata">1.0216 (2)</td><td class="tabledata">0.0176</td><td class="tabledata"></td></tr><tr><td class="tabledata">O12</td><td class="tabledata">0.1533 (3)</td><td class="tabledata">0.58453 (9)</td><td class="tabledata">1.05284 (15)</td><td class="tabledata">0.0237</td><td class="tabledata"></td></tr><tr><td class="tabledata">C13</td><td class="tabledata">0.4420 (4)</td><td class="tabledata">0.65186 (13)</td><td class="tabledata">1.1586 (2)</td><td class="tabledata">0.0214</td><td class="tabledata"></td></tr><tr><td class="tabledata">C14</td><td class="tabledata">0.5889 (5)</td><td class="tabledata">0.68550 (14)</td><td class="tabledata">1.2043 (2)</td><td class="tabledata">0.0247</td><td class="tabledata"></td></tr><tr><td class="tabledata">C15</td><td class="tabledata">0.7515 (5)</td><td class="tabledata">0.69313 (13)</td><td class="tabledata">1.1606 (2)</td><td class="tabledata">0.0235</td><td class="tabledata"></td></tr><tr><td class="tabledata">C16</td><td class="tabledata">0.7717 (4)</td><td class="tabledata">0.66662 (13)</td><td class="tabledata">1.0719 (2)</td><td class="tabledata">0.0211</td><td class="tabledata"></td></tr><tr><td class="tabledata">C17</td><td class="tabledata">0.0513 (5)</td><td class="tabledata">0.44419 (13)</td><td class="tabledata">0.7438 (2)</td><td class="tabledata">0.0227</td><td class="tabledata"></td></tr><tr><td class="tabledata">N18</td><td class="tabledata"><span style="font-family:Times">−</span>0.0763 (4)</td><td class="tabledata">0.41868 (13)</td><td class="tabledata">0.7075 (2)</td><td class="tabledata">0.0334</td><td class="tabledata"></td></tr><tr><td class="tabledata">C19</td><td class="tabledata">0.3871 (5)</td><td class="tabledata">0.45136 (14)</td><td class="tabledata">0.6633 (2)</td><td class="tabledata">0.0244</td><td class="tabledata"></td></tr><tr><td class="tabledata">N20</td><td class="tabledata">0.4065 (4)</td><td class="tabledata">0.42677 (13)</td><td class="tabledata">0.5922 (2)</td><td class="tabledata">0.0372</td><td class="tabledata"></td></tr><tr><td class="tabledata">N21</td><td class="tabledata">0.1269 (3)</td><td class="tabledata">0.65896 (11)</td><td class="tabledata">0.81861 (18)</td><td class="tabledata">0.0185</td><td class="tabledata"></td></tr><tr><td class="tabledata">C22</td><td class="tabledata">0.1456 (4)</td><td class="tabledata">0.63048 (12)</td><td class="tabledata">0.7301 (2)</td><td class="tabledata">0.0193</td><td class="tabledata"></td></tr><tr><td class="tabledata">C23</td><td class="tabledata">0.3046 (5)</td><td class="tabledata">0.63170 (13)</td><td class="tabledata">0.6818 (2)</td><td class="tabledata">0.0227</td><td class="tabledata"></td></tr><tr><td class="tabledata">C24</td><td class="tabledata">0.3041 (5)</td><td class="tabledata">0.60183 (14)</td><td class="tabledata">0.5940 (2)</td><td class="tabledata">0.0281</td><td class="tabledata"></td></tr><tr><td class="tabledata">C25</td><td class="tabledata">0.1478 (5)</td><td class="tabledata">0.57112 (14)</td><td class="tabledata">0.5532 (2)</td><td class="tabledata">0.0305</td><td class="tabledata"></td></tr><tr><td class="tabledata">C26</td><td class="tabledata"><span style="font-family:Times">−</span>0.0103 (5)</td><td class="tabledata">0.56959 (14)</td><td class="tabledata">0.6017 (2)</td><td class="tabledata">0.0289</td><td class="tabledata"></td></tr><tr><td class="tabledata">C27</td><td class="tabledata"><span style="font-family:Times">−</span>0.0132 (5)</td><td class="tabledata">0.59861 (13)</td><td class="tabledata">0.6889 (2)</td><td class="tabledata">0.0227</td><td class="tabledata"></td></tr><tr><td class="tabledata">C28</td><td class="tabledata">0.2398 (4)</td><td class="tabledata">0.69992 (12)</td><td class="tabledata">0.8710 (2)</td><td class="tabledata">0.0172</td><td class="tabledata"></td></tr><tr><td class="tabledata">N29</td><td class="tabledata">0.4071 (3)</td><td class="tabledata">0.71395 (10)</td><td class="tabledata">0.84429 (17)</td><td class="tabledata">0.0189</td><td class="tabledata"></td></tr><tr><td class="tabledata">C30</td><td class="tabledata">0.5047 (4)</td><td class="tabledata">0.75525 (13)</td><td class="tabledata">0.8996 (2)</td><td class="tabledata">0.0204</td><td class="tabledata"></td></tr><tr><td class="tabledata">C31</td><td class="tabledata">0.4355 (4)</td><td class="tabledata">0.78043 (13)</td><td class="tabledata">0.9782 (2)</td><td class="tabledata">0.0240</td><td class="tabledata"></td></tr><tr><td class="tabledata">C32</td><td class="tabledata">0.2624 (5)</td><td class="tabledata">0.76203 (13)</td><td class="tabledata">1.0009 (2)</td><td class="tabledata">0.0233</td><td class="tabledata"></td></tr><tr><td class="tabledata">N33</td><td class="tabledata">0.1612 (3)</td><td class="tabledata">0.72147 (11)</td><td class="tabledata">0.94755 (18)</td><td class="tabledata">0.0203</td><td class="tabledata"></td></tr><tr><td class="tabledata">C34</td><td class="tabledata">0.1768 (5)</td><td class="tabledata">0.78633 (16)</td><td class="tabledata">1.0859 (3)</td><td class="tabledata">0.0350</td><td class="tabledata"></td></tr><tr><td class="tabledata">C35</td><td class="tabledata">0.6919 (4)</td><td class="tabledata">0.77160 (14)</td><td class="tabledata">0.8698 (2)</td><td class="tabledata">0.0256</td><td class="tabledata"></td></tr><tr><td class="tabledata">H131</td><td class="tabledata">0.3325</td><td class="tabledata">0.6473</td><td class="tabledata">1.1887</td><td class="tabledata">0.0272*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H141</td><td class="tabledata">0.5773</td><td class="tabledata">0.7037</td><td class="tabledata">1.2645</td><td class="tabledata">0.0304*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H151</td><td class="tabledata">0.8471</td><td class="tabledata">0.7168</td><td class="tabledata">1.1907</td><td class="tabledata">0.0275*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H161</td><td class="tabledata">0.8807</td><td class="tabledata">0.6722</td><td class="tabledata">1.0421</td><td class="tabledata">0.0261*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H231</td><td class="tabledata">0.4128</td><td class="tabledata">0.6519</td><td class="tabledata">0.7083</td><td class="tabledata">0.0274*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H241</td><td class="tabledata">0.4121</td><td class="tabledata">0.6020</td><td class="tabledata">0.5619</td><td class="tabledata">0.0339*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H251</td><td class="tabledata">0.1519</td><td class="tabledata">0.5519</td><td class="tabledata">0.4941</td><td class="tabledata">0.0370*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H261</td><td class="tabledata"><span style="font-family:Times">−</span>0.1170</td><td class="tabledata">0.5500</td><td class="tabledata">0.5748</td><td class="tabledata">0.0342*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H271</td><td class="tabledata"><span style="font-family:Times">−</span>0.1197</td><td class="tabledata">0.5972</td><td class="tabledata">0.7217</td><td class="tabledata">0.0260*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H311</td><td class="tabledata">0.5042</td><td class="tabledata">0.8085</td><td class="tabledata">1.0170</td><td class="tabledata">0.0294*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H342</td><td class="tabledata">0.0443</td><td class="tabledata">0.7782</td><td class="tabledata">1.0832</td><td class="tabledata">0.0544*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H341</td><td class="tabledata">0.1920</td><td class="tabledata">0.8277</td><td class="tabledata">1.0869</td><td class="tabledata">0.0549*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H343</td><td class="tabledata">0.2423</td><td class="tabledata">0.7710</td><td class="tabledata">1.1438</td><td class="tabledata">0.0548*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H352</td><td class="tabledata">0.7389</td><td class="tabledata">0.8070</td><td class="tabledata">0.9003</td><td class="tabledata">0.0411*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H353</td><td class="tabledata">0.6847</td><td class="tabledata">0.7771</td><td class="tabledata">0.8015</td><td class="tabledata">0.0418*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H351</td><td class="tabledata">0.7800</td><td class="tabledata">0.7420</td><td class="tabledata">0.8872</td><td class="tabledata">0.0415*</td><td class="tabledata"></td></tr><tr><td class="tabledata">H211</td><td class="tabledata">0.022 (3)</td><td class="tabledata">0.6531 (11)</td><td class="tabledata">0.8421 (16)</td><td class="tabledata">0.0231*</td><td class="tabledata"></td></tr></table> </div> <!-- endtablewrapcoordsdiv --> <div class="tablewrapadps"> <a name="atomicdisplacement1"></a> <span class="heading3">Atomic displacement parameters (Å<sup>2</sup>)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table class="tabledata" style="table-layout:fixed" summary="" width="100%"><tr><td class="tabledata"> </td><td class="tabledata"><i>U</i><sup>11</sup></td><td class="tabledata"><i>U</i><sup>22</sup></td><td class="tabledata"><i>U</i><sup>33</sup></td><td class="tabledata"><i>U</i><sup>12</sup></td><td class="tabledata"><i>U</i><sup>13</sup></td><td class="tabledata"><i>U</i><sup>23</sup></td></tr><tr><td class="tabledata">S1</td><td class="tabledata">0.0223</td><td class="tabledata">0.0220</td><td class="tabledata">0.0224</td><td class="tabledata"><span style="font-family:Times">−</span>0.0001</td><td class="tabledata">0.0015</td><td class="tabledata"><span style="font-family:Times">−</span>0.0055</td></tr><tr><td class="tabledata">C2</td><td class="tabledata">0.0274</td><td class="tabledata">0.0150</td><td class="tabledata">0.0197</td><td class="tabledata">0.0019</td><td class="tabledata"><span style="font-family:Times">−</span>0.0035</td><td class="tabledata">0.0014</td></tr><tr><td class="tabledata">C3</td><td class="tabledata">0.0236</td><td class="tabledata">0.0150</td><td class="tabledata">0.0203</td><td class="tabledata"><span style="font-family:Times">−</span>0.0003</td><td class="tabledata"><span style="font-family:Times">−</span>0.0043</td><td class="tabledata">0.0020</td></tr><tr><td class="tabledata">S4</td><td class="tabledata">0.0215</td><td class="tabledata">0.0185</td><td class="tabledata">0.0211</td><td class="tabledata"><span style="font-family:Times">−</span>0.0044</td><td class="tabledata">0.0004</td><td class="tabledata"><span style="font-family:Times">−</span>0.0018</td></tr><tr><td class="tabledata">C5</td><td class="tabledata">0.0202</td><td class="tabledata">0.0125</td><td class="tabledata">0.0189</td><td class="tabledata">0.0022</td><td class="tabledata"><span style="font-family:Times">−</span>0.0038</td><td class="tabledata">0.0041</td></tr><tr><td class="tabledata">C6</td><td class="tabledata">0.0214</td><td class="tabledata">0.0132</td><td class="tabledata">0.0169</td><td class="tabledata">0.0009</td><td class="tabledata"><span style="font-family:Times">−</span>0.0021</td><td class="tabledata">0.0022</td></tr><tr><td class="tabledata">C7</td><td class="tabledata">0.0197</td><td class="tabledata">0.0133</td><td class="tabledata">0.0204</td><td class="tabledata">0.0045</td><td class="tabledata">0.0009</td><td class="tabledata">0.0041</td></tr><tr><td class="tabledata">O8</td><td class="tabledata">0.0219</td><td class="tabledata">0.0229</td><td class="tabledata">0.0214</td><td class="tabledata"><span style="font-family:Times">−</span>0.0035</td><td class="tabledata">0.0027</td><td class="tabledata"><span style="font-family:Times">−</span>0.0011</td></tr><tr><td class="tabledata">C9</td><td class="tabledata">0.0188</td><td class="tabledata">0.0127</td><td class="tabledata">0.0171</td><td class="tabledata">0.0016</td><td class="tabledata"><span style="font-family:Times">−</span>0.0041</td><td class="tabledata">0.0010</td></tr><tr><td class="tabledata">C10</td><td class="tabledata">0.0199</td><td class="tabledata">0.0135</td><td class="tabledata">0.0184</td><td class="tabledata">0.0016</td><td class="tabledata"><span style="font-family:Times">−</span>0.0015</td><td class="tabledata">0.0037</td></tr><tr><td class="tabledata">C11</td><td class="tabledata">0.0187</td><td class="tabledata">0.0143</td><td class="tabledata">0.0198</td><td class="tabledata">0.0015</td><td class="tabledata">0.0023</td><td class="tabledata">0.0054</td></tr><tr><td class="tabledata">O12</td><td class="tabledata">0.0250</td><td class="tabledata">0.0224</td><td class="tabledata">0.0244</td><td class="tabledata"><span style="font-family:Times">−</span>0.0031</td><td class="tabledata">0.0062</td><td class="tabledata">0.0008</td></tr><tr><td class="tabledata">C13</td><td class="tabledata">0.0242</td><td class="tabledata">0.0199</td><td class="tabledata">0.0206</td><td class="tabledata">0.0015</td><td class="tabledata">0.0041</td><td class="tabledata">0.0008</td></tr><tr><td class="tabledata">C14</td><td class="tabledata">0.0338</td><td class="tabledata">0.0223</td><td class="tabledata">0.0175</td><td class="tabledata"><span style="font-family:Times">−</span>0.0007</td><td class="tabledata">0.0016</td><td class="tabledata"><span style="font-family:Times">−</span>0.0052</td></tr><tr><td class="tabledata">C15</td><td class="tabledata">0.0277</td><td class="tabledata">0.0184</td><td class="tabledata">0.0225</td><td class="tabledata"><span style="font-family:Times">−</span>0.0036</td><td class="tabledata"><span style="font-family:Times">−</span>0.0042</td><td class="tabledata"><span style="font-family:Times">−</span>0.0039</td></tr><tr><td class="tabledata">C16</td><td class="tabledata">0.0206</td><td class="tabledata">0.0174</td><td class="tabledata">0.0244</td><td class="tabledata">0.0004</td><td class="tabledata"><span style="font-family:Times">−</span>0.0003</td><td class="tabledata">0.0021</td></tr><tr><td class="tabledata">C17</td><td class="tabledata">0.0271</td><td class="tabledata">0.0205</td><td class="tabledata">0.0195</td><td class="tabledata"><span style="font-family:Times">−</span>0.0001</td><td class="tabledata"><span style="font-family:Times">−</span>0.0013</td><td class="tabledata">0.0002</td></tr><tr><td class="tabledata">N18</td><td class="tabledata">0.0413</td><td class="tabledata">0.0324</td><td class="tabledata">0.0255</td><td class="tabledata"><span style="font-family:Times">−</span>0.0073</td><td class="tabledata">0.0002</td><td class="tabledata"><span style="font-family:Times">−</span>0.0019</td></tr><tr><td class="tabledata">C19</td><td class="tabledata">0.0281</td><td class="tabledata">0.0203</td><td class="tabledata">0.0244</td><td class="tabledata">0.0027</td><td class="tabledata">0.0018</td><td class="tabledata">0.0001</td></tr><tr><td class="tabledata">N20</td><td class="tabledata">0.0423</td><td class="tabledata">0.0377</td><td class="tabledata">0.0314</td><td class="tabledata">0.0023</td><td class="tabledata">0.0037</td><td class="tabledata"><span style="font-family:Times">−</span>0.0076</td></tr><tr><td class="tabledata">N21</td><td class="tabledata">0.0157</td><td class="tabledata">0.0194</td><td class="tabledata">0.0204</td><td class="tabledata"><span style="font-family:Times">−</span>0.0024</td><td class="tabledata">0.0017</td><td class="tabledata"><span style="font-family:Times">−</span>0.0019</td></tr><tr><td class="tabledata">C22</td><td class="tabledata">0.0294</td><td class="tabledata">0.0114</td><td class="tabledata">0.0161</td><td class="tabledata">0.0038</td><td class="tabledata"><span style="font-family:Times">−</span>0.0013</td><td class="tabledata">0.0021</td></tr><tr><td class="tabledata">C23</td><td class="tabledata">0.0284</td><td class="tabledata">0.0181</td><td class="tabledata">0.0215</td><td class="tabledata">0.0000</td><td class="tabledata">0.0027</td><td class="tabledata">0.0018</td></tr><tr><td class="tabledata">C24</td><td class="tabledata">0.0429</td><td class="tabledata">0.0202</td><td class="tabledata">0.0223</td><td class="tabledata">0.0053</td><td class="tabledata">0.0090</td><td class="tabledata">0.0021</td></tr><tr><td class="tabledata">C25</td><td class="tabledata">0.0517</td><td class="tabledata">0.0213</td><td class="tabledata">0.0177</td><td class="tabledata">0.0021</td><td class="tabledata">0.0016</td><td class="tabledata"><span style="font-family:Times">−</span>0.0017</td></tr><tr><td class="tabledata">C26</td><td class="tabledata">0.0429</td><td class="tabledata">0.0167</td><td class="tabledata">0.0242</td><td class="tabledata"><span style="font-family:Times">−</span>0.0026</td><td class="tabledata"><span style="font-family:Times">−</span>0.0075</td><td class="tabledata"><span style="font-family:Times">−</span>0.0005</td></tr><tr><td class="tabledata">C27</td><td class="tabledata">0.0289</td><td class="tabledata">0.0183</td><td class="tabledata">0.0198</td><td class="tabledata">0.0015</td><td class="tabledata"><span style="font-family:Times">−</span>0.0020</td><td class="tabledata">0.0034</td></tr><tr><td class="tabledata">C28</td><td class="tabledata">0.0207</td><td class="tabledata">0.0113</td><td class="tabledata">0.0185</td><td class="tabledata">0.0042</td><td class="tabledata"><span style="font-family:Times">−</span>0.0016</td><td class="tabledata">0.0037</td></tr><tr><td class="tabledata">N29</td><td class="tabledata">0.0213</td><td class="tabledata">0.0152</td><td class="tabledata">0.0199</td><td class="tabledata">0.0012</td><td class="tabledata">0.0007</td><td class="tabledata">0.0033</td></tr><tr><td class="tabledata">C30</td><td class="tabledata">0.0215</td><td class="tabledata">0.0145</td><td class="tabledata">0.0238</td><td class="tabledata">0.0007</td><td class="tabledata"><span style="font-family:Times">−</span>0.0033</td><td class="tabledata">0.0047</td></tr><tr><td class="tabledata">C31</td><td class="tabledata">0.0283</td><td class="tabledata">0.0158</td><td class="tabledata">0.0267</td><td class="tabledata"><span style="font-family:Times">−</span>0.0028</td><td class="tabledata"><span style="font-family:Times">−</span>0.0013</td><td class="tabledata"><span style="font-family:Times">−</span>0.0036</td></tr><tr><td class="tabledata">C32</td><td class="tabledata">0.0270</td><td class="tabledata">0.0190</td><td class="tabledata">0.0235</td><td class="tabledata">0.0016</td><td class="tabledata">0.0019</td><td class="tabledata"><span style="font-family:Times">−</span>0.0027</td></tr><tr><td class="tabledata">N33</td><td class="tabledata">0.0224</td><td class="tabledata">0.0175</td><td class="tabledata">0.0210</td><td class="tabledata">0.0013</td><td class="tabledata">0.0029</td><td class="tabledata"><span style="font-family:Times">−</span>0.0031</td></tr><tr><td class="tabledata">C34</td><td class="tabledata">0.0366</td><td class="tabledata">0.0326</td><td class="tabledata">0.0373</td><td class="tabledata"><span style="font-family:Times">−</span>0.0031</td><td class="tabledata">0.0103</td><td class="tabledata"><span style="font-family:Times">−</span>0.0140</td></tr><tr><td class="tabledata">C35</td><td class="tabledata">0.0244</td><td class="tabledata">0.0239</td><td class="tabledata">0.0278</td><td class="tabledata"><span style="font-family:Times">−</span>0.0050</td><td class="tabledata">0.0004</td><td class="tabledata">0.0034</td></tr></table> </div> <!-- endtablewrapadpsdiv --> <div class="tablewrapgeomlong"> <a name="geometricparameters1"></a> <span class="heading3">Geometric parameters (Å, º)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><!-- startgeom --><table class="tabledata" style="table-layout:fixed" summary="" width="100%"> <colgroup span="4"> <col width="30%" /> <col width="20%" /> <col width="30%" /> <col width="20%" /> </colgroup> <tr><td class="tabledata" width="30%">S1—C2</td><td class="tabledata" width="20%">1.764 (3)</td><td class="tabledata" width="30%">N21—H211</td><td class="tabledata" width="20%">0.864 (17)</td></tr><tr><td class="tabledata" width="30%">S1—C6</td><td class="tabledata" width="20%">1.764 (3)</td><td class="tabledata" width="30%">C22—C23</td><td class="tabledata" width="20%">1.391 (4)</td></tr><tr><td class="tabledata" width="30%">C2—C3</td><td class="tabledata" width="20%">1.343 (4)</td><td class="tabledata" width="30%">C22—C27</td><td class="tabledata" width="20%">1.410 (4)</td></tr><tr><td class="tabledata" width="30%">C2—C19</td><td class="tabledata" width="20%">1.429 (4)</td><td class="tabledata" width="30%">C23—C24</td><td class="tabledata" width="20%">1.390 (4)</td></tr><tr><td class="tabledata" width="30%">C3—S4</td><td class="tabledata" width="20%">1.767 (3)</td><td class="tabledata" width="30%">C23—H231</td><td class="tabledata" width="20%">0.938</td></tr><tr><td class="tabledata" width="30%">C3—C17</td><td class="tabledata" width="20%">1.436 (4)</td><td class="tabledata" width="30%">C24—C25</td><td class="tabledata" width="20%">1.382 (5)</td></tr><tr><td class="tabledata" width="30%">S4—C5</td><td class="tabledata" width="20%">1.763 (3)</td><td class="tabledata" width="30%">C24—H241</td><td class="tabledata" width="20%">0.939</td></tr><tr><td class="tabledata" width="30%">C5—C6</td><td class="tabledata" width="20%">1.336 (4)</td><td class="tabledata" width="30%">C25—C26</td><td class="tabledata" width="20%">1.387 (5)</td></tr><tr><td class="tabledata" width="30%">C5—C11</td><td class="tabledata" width="20%">1.483 (4)</td><td class="tabledata" width="30%">C25—H251</td><td class="tabledata" width="20%">0.930</td></tr><tr><td class="tabledata" width="30%">C6—C7</td><td class="tabledata" width="20%">1.502 (4)</td><td class="tabledata" width="30%">C26—C27</td><td class="tabledata" width="20%">1.378 (4)</td></tr><tr><td class="tabledata" width="30%">C7—O8</td><td class="tabledata" width="20%">1.223 (4)</td><td class="tabledata" width="30%">C26—H261</td><td class="tabledata" width="20%">0.923</td></tr><tr><td class="tabledata" width="30%">C7—C9</td><td class="tabledata" width="20%">1.473 (4)</td><td class="tabledata" width="30%">C27—H271</td><td class="tabledata" width="20%">0.936</td></tr><tr><td class="tabledata" width="30%">C9—C10</td><td class="tabledata" width="20%">1.404 (4)</td><td class="tabledata" width="30%">C28—N29</td><td class="tabledata" width="20%">1.336 (4)</td></tr><tr><td class="tabledata" width="30%">C9—C16</td><td class="tabledata" width="20%">1.393 (4)</td><td class="tabledata" width="30%">C28—N33</td><td class="tabledata" width="20%">1.350 (4)</td></tr><tr><td class="tabledata" width="30%">C10—C11</td><td class="tabledata" width="20%">1.491 (4)</td><td class="tabledata" width="30%">N29—C30</td><td class="tabledata" width="20%">1.353 (4)</td></tr><tr><td class="tabledata" width="30%">C10—C13</td><td class="tabledata" width="20%">1.379 (4)</td><td class="tabledata" width="30%">C30—C31</td><td class="tabledata" width="20%">1.375 (4)</td></tr><tr><td class="tabledata" width="30%">C11—O12</td><td class="tabledata" width="20%">1.222 (4)</td><td class="tabledata" width="30%">C30—C35</td><td class="tabledata" width="20%">1.499 (4)</td></tr><tr><td class="tabledata" width="30%">C13—C14</td><td class="tabledata" width="20%">1.390 (4)</td><td class="tabledata" width="30%">C31—C32</td><td class="tabledata" width="20%">1.382 (5)</td></tr><tr><td class="tabledata" width="30%">C13—H131</td><td class="tabledata" width="20%">0.938</td><td class="tabledata" width="30%">C31—H311</td><td class="tabledata" width="20%">0.935</td></tr><tr><td class="tabledata" width="30%">C14—C15</td><td class="tabledata" width="20%">1.388 (5)</td><td class="tabledata" width="30%">C32—N33</td><td class="tabledata" width="20%">1.339 (4)</td></tr><tr><td class="tabledata" width="30%">C14—H141</td><td class="tabledata" width="20%">0.944</td><td class="tabledata" width="30%">C32—C34</td><td class="tabledata" width="20%">1.498 (4)</td></tr><tr><td class="tabledata" width="30%">C15—C16</td><td class="tabledata" width="20%">1.390 (4)</td><td class="tabledata" width="30%">C34—H342</td><td class="tabledata" width="20%">0.964</td></tr><tr><td class="tabledata" width="30%">C15—H151</td><td class="tabledata" width="20%">0.931</td><td class="tabledata" width="30%">C34—H341</td><td class="tabledata" width="20%">0.950</td></tr><tr><td class="tabledata" width="30%">C16—H161</td><td class="tabledata" width="20%">0.936</td><td class="tabledata" width="30%">C34—H343</td><td class="tabledata" width="20%">0.944</td></tr><tr><td class="tabledata" width="30%">C17—N18</td><td class="tabledata" width="20%">1.146 (4)</td><td class="tabledata" width="30%">C35—H352</td><td class="tabledata" width="20%">0.952</td></tr><tr><td class="tabledata" width="30%">C19—N20</td><td class="tabledata" width="20%">1.155 (4)</td><td class="tabledata" width="30%">C35—H353</td><td class="tabledata" width="20%">0.949</td></tr><tr><td class="tabledata" width="30%">N21—C22</td><td class="tabledata" width="20%">1.406 (4)</td><td class="tabledata" width="30%">C35—H351</td><td class="tabledata" width="20%">0.935</td></tr><tr><td class="tabledata" width="30%">N21—C28</td><td class="tabledata" width="20%">1.382 (4)</td><td class="tabledata"> </td><td class="tabledata"> </td></tr><tr><td class="tabledata" width="25%"></td><td class="tabledata" width="25%"></td><td class="tabledata" width="25%"></td><td class="tabledata" width="25%"></td></tr><tr><td class="tabledata" width="30%">C2—S1—C6</td><td class="tabledata" width="20%">101.45 (14)</td><td class="tabledata" width="30%">N21—C22—C27</td><td class="tabledata" width="20%">115.5 (3)</td></tr><tr><td class="tabledata" width="30%">S1—C2—C3</td><td class="tabledata" width="20%">128.4 (2)</td><td class="tabledata" width="30%">C23—C22—C27</td><td class="tabledata" width="20%">119.0 (3)</td></tr><tr><td class="tabledata" width="30%">S1—C2—C19</td><td class="tabledata" width="20%">111.8 (2)</td><td class="tabledata" width="30%">C22—C23—C24</td><td class="tabledata" width="20%">119.6 (3)</td></tr><tr><td class="tabledata" width="30%">C3—C2—C19</td><td class="tabledata" width="20%">119.7 (3)</td><td class="tabledata" width="30%">C22—C23—H231</td><td class="tabledata" width="20%">120.6</td></tr><tr><td class="tabledata" width="30%">C2—C3—S4</td><td class="tabledata" width="20%">129.0 (2)</td><td class="tabledata" width="30%">C24—C23—H231</td><td class="tabledata" width="20%">119.7</td></tr><tr><td class="tabledata" width="30%">C2—C3—C17</td><td class="tabledata" width="20%">120.4 (3)</td><td class="tabledata" width="30%">C23—C24—C25</td><td class="tabledata" width="20%">121.3 (3)</td></tr><tr><td class="tabledata" width="30%">S4—C3—C17</td><td class="tabledata" width="20%">110.6 (2)</td><td class="tabledata" width="30%">C23—C24—H241</td><td class="tabledata" width="20%">119.7</td></tr><tr><td class="tabledata" width="30%">C3—S4—C5</td><td class="tabledata" width="20%">101.35 (14)</td><td class="tabledata" width="30%">C25—C24—H241</td><td class="tabledata" width="20%">118.9</td></tr><tr><td class="tabledata" width="30%">S4—C5—C6</td><td class="tabledata" width="20%">128.9 (2)</td><td class="tabledata" width="30%">C24—C25—C26</td><td class="tabledata" width="20%">119.0 (3)</td></tr><tr><td class="tabledata" width="30%">S4—C5—C11</td><td class="tabledata" width="20%">108.9 (2)</td><td class="tabledata" width="30%">C24—C25—H251</td><td class="tabledata" width="20%">119.1</td></tr><tr><td class="tabledata" width="30%">C6—C5—C11</td><td class="tabledata" width="20%">122.2 (3)</td><td class="tabledata" width="30%">C26—C25—H251</td><td class="tabledata" width="20%">121.9</td></tr><tr><td class="tabledata" width="30%">S1—C6—C5</td><td class="tabledata" width="20%">129.0 (2)</td><td class="tabledata" width="30%">C25—C26—C27</td><td class="tabledata" width="20%">120.8 (3)</td></tr><tr><td class="tabledata" width="30%">S1—C6—C7</td><td class="tabledata" width="20%">110.7 (2)</td><td class="tabledata" width="30%">C25—C26—H261</td><td class="tabledata" width="20%">120.2</td></tr><tr><td class="tabledata" width="30%">C5—C6—C7</td><td class="tabledata" width="20%">120.3 (3)</td><td class="tabledata" width="30%">C27—C26—H261</td><td class="tabledata" width="20%">118.9</td></tr><tr><td class="tabledata" width="30%">C6—C7—O8</td><td class="tabledata" width="20%">118.0 (3)</td><td class="tabledata" width="30%">C22—C27—C26</td><td class="tabledata" width="20%">120.2 (3)</td></tr><tr><td class="tabledata" width="30%">C6—C7—C9</td><td class="tabledata" width="20%">118.3 (3)</td><td class="tabledata" width="30%">C22—C27—H271</td><td class="tabledata" width="20%">119.3</td></tr><tr><td class="tabledata" width="30%">O8—C7—C9</td><td class="tabledata" width="20%">123.6 (3)</td><td class="tabledata" width="30%">C26—C27—H271</td><td class="tabledata" width="20%">120.5</td></tr><tr><td class="tabledata" width="30%">C7—C9—C10</td><td class="tabledata" width="20%">120.6 (3)</td><td class="tabledata" width="30%">N21—C28—N29</td><td class="tabledata" width="20%">120.3 (3)</td></tr><tr><td class="tabledata" width="30%">C7—C9—C16</td><td class="tabledata" width="20%">119.7 (3)</td><td class="tabledata" width="30%">N21—C28—N33</td><td class="tabledata" width="20%">112.5 (3)</td></tr><tr><td class="tabledata" width="30%">C10—C9—C16</td><td class="tabledata" width="20%">119.7 (3)</td><td class="tabledata" width="30%">N29—C28—N33</td><td class="tabledata" width="20%">127.2 (3)</td></tr><tr><td class="tabledata" width="30%">C9—C10—C11</td><td class="tabledata" width="20%">119.3 (3)</td><td class="tabledata" width="30%">C28—N29—C30</td><td class="tabledata" width="20%">115.5 (3)</td></tr><tr><td class="tabledata" width="30%">C9—C10—C13</td><td class="tabledata" width="20%">120.7 (3)</td><td class="tabledata" width="30%">N29—C30—C31</td><td class="tabledata" width="20%">121.7 (3)</td></tr><tr><td class="tabledata" width="30%">C11—C10—C13</td><td class="tabledata" width="20%">119.9 (3)</td><td class="tabledata" width="30%">N29—C30—C35</td><td class="tabledata" width="20%">115.9 (3)</td></tr><tr><td class="tabledata" width="30%">C10—C11—C5</td><td class="tabledata" width="20%">118.2 (3)</td><td class="tabledata" width="30%">C31—C30—C35</td><td class="tabledata" width="20%">122.4 (3)</td></tr><tr><td class="tabledata" width="30%">C10—C11—O12</td><td class="tabledata" width="20%">122.1 (3)</td><td class="tabledata" width="30%">C30—C31—C32</td><td class="tabledata" width="20%">118.3 (3)</td></tr><tr><td class="tabledata" width="30%">C5—C11—O12</td><td class="tabledata" width="20%">119.6 (3)</td><td class="tabledata" width="30%">C30—C31—H311</td><td class="tabledata" width="20%">121.5</td></tr><tr><td class="tabledata" width="30%">C10—C13—C14</td><td class="tabledata" width="20%">119.5 (3)</td><td class="tabledata" width="30%">C32—C31—H311</td><td class="tabledata" width="20%">120.2</td></tr><tr><td class="tabledata" width="30%">C10—C13—H131</td><td class="tabledata" width="20%">121.3</td><td class="tabledata" width="30%">C31—C32—N33</td><td class="tabledata" width="20%">121.7 (3)</td></tr><tr><td class="tabledata" width="30%">C14—C13—H131</td><td class="tabledata" width="20%">119.3</td><td class="tabledata" width="30%">C31—C32—C34</td><td class="tabledata" width="20%">122.1 (3)</td></tr><tr><td class="tabledata" width="30%">C13—C14—C15</td><td class="tabledata" width="20%">120.1 (3)</td><td class="tabledata" width="30%">N33—C32—C34</td><td class="tabledata" width="20%">116.2 (3)</td></tr><tr><td class="tabledata" width="30%">C13—C14—H141</td><td class="tabledata" width="20%">120.0</td><td class="tabledata" width="30%">C28—N33—C32</td><td class="tabledata" width="20%">115.6 (3)</td></tr><tr><td class="tabledata" width="30%">C15—C14—H141</td><td class="tabledata" width="20%">119.9</td><td class="tabledata" width="30%">C32—C34—H342</td><td class="tabledata" width="20%">113.2</td></tr><tr><td class="tabledata" width="30%">C14—C15—C16</td><td class="tabledata" width="20%">120.9 (3)</td><td class="tabledata" width="30%">C32—C34—H341</td><td class="tabledata" width="20%">108.8</td></tr><tr><td class="tabledata" width="30%">C14—C15—H151</td><td class="tabledata" width="20%">119.4</td><td class="tabledata" width="30%">H342—C34—H341</td><td class="tabledata" width="20%">107.6</td></tr><tr><td class="tabledata" width="30%">C16—C15—H151</td><td class="tabledata" width="20%">119.7</td><td class="tabledata" width="30%">C32—C34—H343</td><td class="tabledata" width="20%">108.7</td></tr><tr><td class="tabledata" width="30%">C9—C16—C15</td><td class="tabledata" width="20%">119.1 (3)</td><td class="tabledata" width="30%">H342—C34—H343</td><td class="tabledata" width="20%">110.3</td></tr><tr><td class="tabledata" width="30%">C9—C16—H161</td><td class="tabledata" width="20%">120.1</td><td class="tabledata" width="30%">H341—C34—H343</td><td class="tabledata" width="20%">108.1</td></tr><tr><td class="tabledata" width="30%">C15—C16—H161</td><td class="tabledata" width="20%">120.8</td><td class="tabledata" width="30%">C30—C35—H352</td><td class="tabledata" width="20%">111.7</td></tr><tr><td class="tabledata" width="30%">C3—C17—N18</td><td class="tabledata" width="20%">177.7 (3)</td><td class="tabledata" width="30%">C30—C35—H353</td><td class="tabledata" width="20%">111.4</td></tr><tr><td class="tabledata" width="30%">C2—C19—N20</td><td class="tabledata" width="20%">178.1 (3)</td><td class="tabledata" width="30%">H352—C35—H353</td><td class="tabledata" width="20%">107.6</td></tr><tr><td class="tabledata" width="30%">C22—N21—C28</td><td class="tabledata" width="20%">131.0 (3)</td><td class="tabledata" width="30%">C30—C35—H351</td><td class="tabledata" width="20%">110.5</td></tr><tr><td class="tabledata" width="30%">C22—N21—H211</td><td class="tabledata" width="20%">115.8 (12)</td><td class="tabledata" width="30%">H352—C35—H351</td><td class="tabledata" width="20%">107.8</td></tr><tr><td class="tabledata" width="30%">C28—N21—H211</td><td class="tabledata" width="20%">112.8 (12)</td><td class="tabledata" width="30%">H353—C35—H351</td><td class="tabledata" width="20%">107.7</td></tr><tr><td class="tabledata" width="30%">N21—C22—C23</td><td class="tabledata" width="20%">125.5 (3)</td><td class="tabledata"> </td><td class="tabledata"> </td></tr></table> </div> <!-- endtablewrapgeomlongdiv --> <div class="tablewraphbondslong"> <a name="hydrogen-bondgeometry1"></a> <span class="heading3">Hydrogen-bond geometry (Å, º)</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table class="tabledata" style="table-layout:fixed" summary="" width="100%"> <colgroup span="5"> <col width="40%" /> <col width="15%" /> <col width="15%" /> <col width="15%" /> <col width="15%" /> </colgroup> <tr><td class="tabledata" width="40%"><i>D</i>—H···<i>A</i></td><td class="tabledata" width="15%"><i>D</i>—H</td><td class="tabledata" width="15%">H···<i>A</i></td><td class="tabledata" width="15%"><i>D</i>···<i>A</i></td><td class="tabledata" width="15%"><i>D</i>—H···<i>A</i></td></tr><tr><td class="tabledata" width="40%">C23—H231···N29</td><td class="tabledata" width="15%">0.94</td><td class="tabledata" width="15%">2.36</td><td class="tabledata" width="15%">2.950 (4)</td><td class="tabledata" width="15%">121 (1)</td></tr><tr><td class="tabledata" width="40%">C27—H271···O8<sup>i</sup></td><td class="tabledata" width="15%">0.94</td><td class="tabledata" width="15%">2.51</td><td class="tabledata" width="15%">3.296 (4)</td><td class="tabledata" width="15%">141 (1)</td></tr><tr><td class="tabledata" width="40%">N21—H211···O8<sup>i</sup></td><td class="tabledata" width="15%">0.86</td><td class="tabledata" width="15%">2.15</td><td class="tabledata" width="15%">2.985 (4)</td><td class="tabledata" width="15%">162 (2)</td></tr></table><table class="noborder" style="table-layout:fixed" width="100%"><tr><td class="tabledata">Symmetry code: (i) <i>x</i><span style="font-family:Times">−</span>1, <i>y</i>, <i>z</i>.</td></tr></table> </div> <!-- endtablewraphbondslongdiv --> </div> <!-- enddatablockdiv --> <div class="datablock999"> <div class="tablewrapxtablepubl"> <span class="heading3"><!-- <span class="tablenum"><b>Table 1</b></span><br /> -->Comparison of calculated (GIPAW)<sup>a</sup> and experimental <sup>13</sup>C and <sup>1</sup>H NMR chemical shifts (in ppm) in the DI–PM cocrystal<sup>b</sup></span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table class="tabledata" style="table-layout:fixed" summary="" width="100%"><tr><td class="tabledata" width="16%">Atom label</td><td class="tabledata" width="16%"><sup>13</sup>C</td><td class="tabledata" width="16%"><sup>1</sup>H</td><td class="tabledata" width="16%"></td><td class="tabledata" width="16%"></td><td class="tabledata" width="16%"></td></tr><tr><td class="tabledata" width="16%">C</td><td class="tabledata" width="16%">H</td><td class="tabledata" width="16%"><span style="font-family:Times">δ</span><sub>calc</sub></td><td class="tabledata" width="16%"><span style="font-family:Times">δ</span><sub>expt</sub></td><td class="tabledata" width="16%"><span style="font-family:Times">δ</span><sub>calc</sub></td><td class="tabledata" width="16%"><span style="font-family:Times">δ</span><sub>expt</sub></td></tr><tr><td class="tabledata" width="16%">C65</td><td class="tabledata" width="16%">H22/H23/H24<sup>c</sup></td><td class="tabledata" width="16%">15.3</td><td class="tabledata" width="16%">23.9</td><td class="tabledata" width="16%">1.8</td><td class="tabledata" width="16%">1.9</td></tr><tr><td class="tabledata" width="16%">C68</td><td class="tabledata" width="16%">H26/H27/H28<sup>c</sup></td><td class="tabledata" width="16%">17.2</td><td class="tabledata" width="16%">25.7</td><td class="tabledata" width="16%">2.0</td><td class="tabledata" width="16%">2.0</td></tr><tr><td class="tabledata" width="16%">C66</td><td class="tabledata" width="16%">H25</td><td class="tabledata" width="16%">111.5</td><td class="tabledata" width="16%">112.6</td><td class="tabledata" width="16%">3.4</td><td class="tabledata" width="16%">4.0</td></tr><tr><td class="tabledata" width="16%">C1</td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">113.8</td><td class="tabledata" width="16%">114.4<sup>d</sup></td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">-</td></tr><tr><td class="tabledata" width="16%">C14</td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">114.5</td><td class="tabledata" width="16%">114.4<sup>d</sup></td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">-</td></tr><tr><td class="tabledata" width="16%">C2</td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">115.5</td><td class="tabledata" width="16%">114.4<sup>d</sup></td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">-</td></tr><tr><td class="tabledata" width="16%">C13</td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">115.9</td><td class="tabledata" width="16%">114.4<sup>d</sup></td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">-</td></tr><tr><td class="tabledata" width="16%">C58</td><td class="tabledata" width="16%">H17</td><td class="tabledata" width="16%">120.1</td><td class="tabledata" width="16%">119.4</td><td class="tabledata" width="16%">9.7</td><td class="tabledata" width="16%">9.1</td></tr><tr><td class="tabledata" width="16%">C62</td><td class="tabledata" width="16%">H21</td><td class="tabledata" width="16%">120.2</td><td class="tabledata" width="16%">120.3</td><td class="tabledata" width="16%">8.4</td><td class="tabledata" width="16%">8.0</td></tr><tr><td class="tabledata" width="16%">C9</td><td class="tabledata" width="16%">H1</td><td class="tabledata" width="16%">126.7</td><td class="tabledata" width="16%">125.7</td><td class="tabledata" width="16%">7.4</td><td class="tabledata" width="16%">7.4</td></tr><tr><td class="tabledata" width="16%">C7</td><td class="tabledata" width="16%"><i>H1<sup>e</sup></i></td><td class="tabledata" width="16%">126.8</td><td class="tabledata" width="16%">125.7</td><td class="tabledata" width="16%"><i>7.4</i></td><td class="tabledata" width="16%"><i>7.4</i></td></tr><tr><td class="tabledata" width="16%">C61</td><td class="tabledata" width="16%">H20</td><td class="tabledata" width="16%">127.7</td><td class="tabledata" width="16%">127.7</td><td class="tabledata" width="16%">7.6</td><td class="tabledata" width="16%">7.4</td></tr><tr><td class="tabledata" width="16%">C12</td><td class="tabledata" width="16%">H4</td><td class="tabledata" width="16%">128.5</td><td class="tabledata" width="16%">129.8</td><td class="tabledata" width="16%">8.5</td><td class="tabledata" width="16%">8.2</td></tr><tr><td class="tabledata" width="16%">C6</td><td class="tabledata" width="16%"><i>H4<sup>e</sup></i></td><td class="tabledata" width="16%">128.6</td><td class="tabledata" width="16%">129.8</td><td class="tabledata" width="16%"><i>8.5</i></td><td class="tabledata" width="16%"><i>8.2</i></td></tr><tr><td class="tabledata" width="16%">C60</td><td class="tabledata" width="16%">H19</td><td class="tabledata" width="16%">129.3</td><td class="tabledata" width="16%">130.2</td><td class="tabledata" width="16%">7.3</td><td class="tabledata" width="16%">7.8</td></tr><tr><td class="tabledata" width="16%">C4</td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">130.1</td><td class="tabledata" width="16%">131.1<sup>d</sup></td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">-</td></tr><tr><td class="tabledata" width="16%">C59</td><td class="tabledata" width="16%">H18</td><td class="tabledata" width="16%">131.5</td><td class="tabledata" width="16%">131.2</td><td class="tabledata" width="16%">7.7</td><td class="tabledata" width="16%">7.7</td></tr><tr><td class="tabledata" width="16%">C10</td><td class="tabledata" width="16%">H2</td><td class="tabledata" width="16%">132.6</td><td class="tabledata" width="16%">133.9</td><td class="tabledata" width="16%">5.9</td><td class="tabledata" width="16%">6.2</td></tr><tr><td class="tabledata" width="16%">C11</td><td class="tabledata" width="16%">H3</td><td class="tabledata" width="16%">139.2</td><td class="tabledata" width="16%">136.8</td><td class="tabledata" width="16%">7.6</td><td class="tabledata" width="16%">7.7</td></tr><tr><td class="tabledata" width="16%">C57</td><td class="tabledata" width="16%"><i>H21, H17, H29</i></td><td class="tabledata" width="16%">138.5</td><td class="tabledata" width="16%">141.5</td><td class="tabledata" width="16%"><i>8.4, 9.7, 10.5</i></td><td class="tabledata" width="16%"><i>8.9</i></td></tr><tr><td class="tabledata" width="16%">C3</td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">139.7</td><td class="tabledata" width="16%">141.4<sup>d</sup></td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">-</td></tr><tr><td class="tabledata" width="16%">C63</td><td class="tabledata" width="16%"><i>H29</i></td><td class="tabledata" width="16%">155.5</td><td class="tabledata" width="16%">160.1</td><td class="tabledata" width="16%"><i>10.5</i></td><td class="tabledata" width="16%"><i>9.1</i></td></tr><tr><td class="tabledata" width="16%">C67</td><td class="tabledata" width="16%"><i>H26/H27/H28, H25</i></td><td class="tabledata" width="16%">168.2</td><td class="tabledata" width="16%">168.2</td><td class="tabledata" width="16%"><i>2.0, 3.4</i></td><td class="tabledata" width="16%"><i>2.8</i></td></tr><tr><td class="tabledata" width="16%">C64</td><td class="tabledata" width="16%"><i>H22/H23/H24, H25</i></td><td class="tabledata" width="16%">168.4</td><td class="tabledata" width="16%">168.2</td><td class="tabledata" width="16%"><i>1.8, 3.4</i></td><td class="tabledata" width="16%"><i>2.8</i></td></tr><tr><td class="tabledata" width="16%">C5</td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">179.7</td><td class="tabledata" width="16%">176.5<sup>d</sup></td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">-</td></tr><tr><td class="tabledata" width="16%">C8</td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">179.9</td><td class="tabledata" width="16%">178.2<sup>d</sup></td><td class="tabledata" width="16%">-</td><td class="tabledata" width="16%">-</td></tr></table><table class="noborder" style="table-layout:fixed" width="100%"><tr><td class="tabledata">Notes: (a) Calculated isotropic chemical shieldings are determined from calculated chemical shieldings according to ?calc = ?ref ? ?calc, where ?ref equals 30.0 ppm for 1H and 163.2 ppm for 13C. b H atom labels and calculated and experimental 1H chemical shifts are presented in normal font for direct one-bond CH connectivities, while longer-range C···H proximities (corresponding to cross peaks observed in the 1H-13C spectra presented in Figs. 4b and 4c) are presented in italics. c For CH3 groups, the calculated 1H chemical shifts correspond to the average over the three hydrogen atoms. d Experimental chemical shifts taken from 13C CP MAS spectrum (Fig. 2a) since no cross peaks are observed in the 1H-13C spectra presented in Figs. 4b and 4c. e Note that the C7-H1 and C6-H4 cross peaks due to longer-range C···H proximities cannot be distinguished from C9-H1 and C12-H4 cross peaks due to one-bond CH connectivities ? in the stick spectrum in Fig. 2b, open bars denote the calculated (GIPAW) C7 and C6 13C chemical shifts.</td></tr></table> </div> <!-- endtablewrapxtablepubldiv --> <div class="tablewrapxtablepubl"> <span class="heading3"><!-- <span class="tablenum"><b>Table 2</b></span><br /> -->Table 2 Comparison of experimental 1H chemical shifts with calculateda (GIPAW) values (all in ppm) for the DI–PM cocrystal for the full <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure</a> and an isolated dithianon or pyrimethanil molecule</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table class="tabledata" style="table-layout:fixed" summary="" width="100%"><tr><td class="tabledata" width="20%">Atom</td><td class="tabledata" width="20%"><span style="font-family:Times">δ</span><sub>exp</sub></td><td class="tabledata" width="20%"><span style="font-family:Times">δ</span><sub>crystal</sub></td><td class="tabledata" width="20%"><span style="font-family:Times">δ</span><sub>molecule</sub></td><td class="tabledata" width="20%">Δ<span style="font-family:Times">δ</span><sub>crystal-molecule</sub></td></tr><tr><td class="tabledata" width="20%">H1</td><td class="tabledata" width="20%">7.4</td><td class="tabledata" width="20%">7.4</td><td class="tabledata" width="20%">7.8</td><td class="tabledata" width="20%">?0.4</td></tr><tr><td class="tabledata" width="20%">H2</td><td class="tabledata" width="20%">6.2</td><td class="tabledata" width="20%">5.9</td><td class="tabledata" width="20%">7.4</td><td class="tabledata" width="20%">?1.5</td></tr><tr><td class="tabledata" width="20%">H3</td><td class="tabledata" width="20%">7.7</td><td class="tabledata" width="20%">7.6</td><td class="tabledata" width="20%">7.4</td><td class="tabledata" width="20%">0.2</td></tr><tr><td class="tabledata" width="20%">H4</td><td class="tabledata" width="20%">8.2</td><td class="tabledata" width="20%">8.5</td><td class="tabledata" width="20%">7.8</td><td class="tabledata" width="20%">0.7</td></tr><tr><td class="tabledata" width="20%">H17</td><td class="tabledata" width="20%">9.1</td><td class="tabledata" width="20%">9.7</td><td class="tabledata" width="20%">9.2</td><td class="tabledata" width="20%">0.5</td></tr><tr><td class="tabledata" width="20%">H18</td><td class="tabledata" width="20%">7.7</td><td class="tabledata" width="20%">7.7</td><td class="tabledata" width="20%">7.0</td><td class="tabledata" width="20%">0.7</td></tr><tr><td class="tabledata" width="20%">H19</td><td class="tabledata" width="20%">7.8</td><td class="tabledata" width="20%">7.3</td><td class="tabledata" width="20%">6.6</td><td class="tabledata" width="20%">0.7</td></tr><tr><td class="tabledata" width="20%">H20</td><td class="tabledata" width="20%">7.4</td><td class="tabledata" width="20%">7.6</td><td class="tabledata" width="20%">7.0</td><td class="tabledata" width="20%">0.6</td></tr><tr><td class="tabledata" width="20%">H21</td><td class="tabledata" width="20%">8.0</td><td class="tabledata" width="20%">8.4</td><td class="tabledata" width="20%">6.4</td><td class="tabledata" width="20%">2.0</td></tr><tr><td class="tabledata" width="20%">H22/23/24<sup>b</sup></td><td class="tabledata" width="20%">1.9</td><td class="tabledata" width="20%">1.8</td><td class="tabledata" width="20%">1.9</td><td class="tabledata" width="20%">?0.1</td></tr><tr><td class="tabledata" width="20%">H25</td><td class="tabledata" width="20%">4.0</td><td class="tabledata" width="20%">3.4</td><td class="tabledata" width="20%">6.1</td><td class="tabledata" width="20%">?2.7</td></tr><tr><td class="tabledata" width="20%">H26/27/28<sup>b</sup></td><td class="tabledata" width="20%">2.0</td><td class="tabledata" width="20%">2.0</td><td class="tabledata" width="20%">1.8</td><td class="tabledata" width="20%">0.2</td></tr><tr><td class="tabledata" width="20%">H29</td><td class="tabledata" width="20%">9.1</td><td class="tabledata" width="20%">10.5</td><td class="tabledata" width="20%">6.9</td><td class="tabledata" width="20%">3.6</td></tr></table><table class="noborder" style="table-layout:fixed" width="100%"><tr><td class="tabledata">Notes: (<i>a</i>) calculated isotropic chemical shieldings are determined from calculated chemical shieldings according to ?calc = ?ref ? ?calc, where ?ref equals 30.0 ppm; (<i>b</i>) For CH3 groups, the calculated 1H chemical shifts correspond to the average over the three hydrogen atoms.</td></tr></table> </div> <!-- endtablewrapxtablepubldiv --> <div class="tablewrapxtablepubl"> <span class="heading3"><!-- <span class="tablenum"><b>Table 3</b></span><br /> -->Table 3 Comparison of calculated (GIPAW) NMR chemical shieldings (in ppm) for the DI–PM cocrystal for the full <a target='Navigator' class="ref_lookup_yellow hideyellow" href='https://dictionary.iucr.org/Crystal_structure' onclick="return makeSubWindow("https://dictionary.iucr.org/Crystal_structure", 'Navigator')">crystal structure</a> and an isolated dithianon or pyrimethanil molecule</span><!-- endheading3span --> <span class="toplink"><a class="buttons" href="#top">top</a></span><!-- endtoplinkspan --><table class="tabledata" style="table-layout:fixed" summary="" width="100%"><tr><td class="tabledata" width="25%">Atom</td><td class="tabledata" width="25%"><span style="font-family:Times">σ</span><sub>molecule</sub></td><td class="tabledata" width="25%"><span style="font-family:Times">σ</span><sub>crystal</sub></td><td class="tabledata" width="25%"><span style="font-family:Times">σ</span><sub>crystal-molecule</sub></td></tr><tr><td class="tabledata" width="25%">N1</td><td class="tabledata" width="25%">?106.4</td><td class="tabledata" width="25%">?88.9</td><td class="tabledata" width="25%">17.5</td></tr><tr><td class="tabledata" width="25%">N2</td><td class="tabledata" width="25%">?107.2</td><td class="tabledata" width="25%">?88.9</td><td class="tabledata" width="25%">18.3</td></tr><tr><td class="tabledata" width="25%">N9</td><td class="tabledata" width="25%">98.9</td><td class="tabledata" width="25%">91.4</td><td class="tabledata" width="25%">?7.4</td></tr><tr><td class="tabledata" width="25%">N10</td><td class="tabledata" width="25%">?30.1</td><td class="tabledata" width="25%">?33.0</td><td class="tabledata" width="25%">?2.9</td></tr><tr><td class="tabledata" width="25%">N11</td><td class="tabledata" width="25%">?44.5</td><td class="tabledata" width="25%">?42.4</td><td class="tabledata" width="25%">2.1</td></tr><tr><td class="tabledata" width="25%">O1</td><td class="tabledata" width="25%">?363.4</td><td class="tabledata" width="25%">?265.9</td><td class="tabledata" width="25%">?97.6</td></tr><tr><td class="tabledata" width="25%">O2</td><td class="tabledata" width="25%">?345.3</td><td class="tabledata" width="25%">?322.2</td><td class="tabledata" width="25%">?23.1</td></tr><tr><td class="tabledata" width="25%">S1</td><td class="tabledata" width="25%">330.7</td><td class="tabledata" width="25%">305.6</td><td class="tabledata" width="25%">25.1</td></tr><tr><td class="tabledata" width="25%">S2</td><td class="tabledata" width="25%">333.8</td><td class="tabledata" width="25%">320.6</td><td class="tabledata" width="25%">13.2</td></tr></table> </div> <!-- endtablewrapxtablepubldiv --> </div> <!-- enddatablockdiv -->  </div> </div> </div> <div id="bm"> <div id="ack"> <h3>Acknowledgements</h3><p>ACP was supported by a Feodor Lynen Research Fellowship of the Alexander von Humboldt Foundation and a Newton Inter­national Fellowship of the Royal Society. EC and HP acknowledge funding from the Mol­ecular Analytical Sciences Centre for Doctoral Training (EPSRC grant EP/L015307/1). We thank Peter Howe (Syngenta) for helpful discussions. Computational facilities were provided by the MidPlus Regional Centre of Excellence for Computational Science, Engineering and Mathematics, under EPSRC grant EP/K000128/1, and the University of Warwick Scientific Computing Research Technology Platform. The 700 MHz NMR spectrometer was partially funded from the European Research Council under the European Union's Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement 639907 (for Dr J. R. Lewandowski, Department of Chemistry, University of Warwick). The experimental and calculated data for this study are provided as a supporting data set from WRAP, the Warwick Research Archive Portal, at <a href="https://wrap.warwick.ac.uk/85381">https://wrap.warwick.ac.uk/85381</a>.</p></div> <div id="bibl"> <h3><a id="References"></a>References</h3><p><span class="font_size_3 bb"><a href="#sourceBB1"><img alt="First citation" class="bibarrow" src="../../../../../../logos/arrows/c_uparr.gif" title="First citation" /></a><a class="bbanchor" id="BB1"></a>Aakeroy, C. B. & Salmon, D. J. 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