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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Bis[1-benzyl-2-(1,3-thiazol-4-yl)-1<italic>H</italic>-benzimidazole-κ<sup>2</sup><italic>N</italic><sup>2</sup>,<italic>N</italic><sup>3</sup>]dichloridocobalt(II)</title><author><name sortKey="Gueddar, Hicham" sort="Gueddar, Hicham" uniqKey="Gueddar H" first="Hicham" last="Gueddar">Hicham Gueddar</name><affiliation><nlm:aff id="a">Laboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat,<country>Morocco</country></nlm:aff></affiliation><affiliation><nlm:aff id="b">Institute of Nanomaterials and Nanotechnology, MAScIR, Avenue de l’Armée Royale, Rabat,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Bouhfid, Rachid" sort="Bouhfid, Rachid" uniqKey="Bouhfid R" first="Rachid" last="Bouhfid">Rachid Bouhfid</name><affiliation><nlm:aff id="b">Institute of Nanomaterials and Nanotechnology, MAScIR, Avenue de l’Armée Royale, Rabat,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Essassi, El Mokhtar" sort="Essassi, El Mokhtar" uniqKey="Essassi E" first="El Mokhtar" last="Essassi">El Mokhtar Essassi</name><affiliation><nlm:aff id="a">Laboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat,<country>Morocco</country></nlm:aff></affiliation><affiliation><nlm:aff id="b">Institute of Nanomaterials and Nanotechnology, MAScIR, Avenue de l’Armée Royale, Rabat,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="El Brahmi, Nabil" sort="El Brahmi, Nabil" uniqKey="El Brahmi N" first="Nabil" last="El Brahmi">Nabil El Brahmi</name><affiliation><nlm:aff id="c">Laboratoire de Chimie Organique Hétérocyclique, URAC 21, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></nlm:aff></affiliation><affiliation><nlm:aff id="d">Laboratoire de Chimie de Coordination, Équipe Dendrimères et Hétérochimie, Toulouse,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="El Ammari, Lahcen" sort="El Ammari, Lahcen" uniqKey="El Ammari L" first="Lahcen" last="El Ammari">Lahcen El Ammari</name><affiliation><nlm:aff id="e">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">23476345</idno><idno type="pmc">3588380</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588380</idno><idno type="RBID">PMC:3588380</idno><idno type="doi">10.1107/S1600536812048751</idno><date when="2012">2012</date><idno type="wicri:Area/Pmc/Corpus">000362</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000362</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Bis[1-benzyl-2-(1,3-thiazol-4-yl)-1<italic>H</italic>-benzimidazole-κ<sup>2</sup><italic>N</italic><sup>2</sup>,<italic>N</italic><sup>3</sup>]dichloridocobalt(II)</title><author><name sortKey="Gueddar, Hicham" sort="Gueddar, Hicham" uniqKey="Gueddar H" first="Hicham" last="Gueddar">Hicham Gueddar</name><affiliation><nlm:aff id="a">Laboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat,<country>Morocco</country></nlm:aff></affiliation><affiliation><nlm:aff id="b">Institute of Nanomaterials and Nanotechnology, MAScIR, Avenue de l’Armée Royale, Rabat,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Bouhfid, Rachid" sort="Bouhfid, Rachid" uniqKey="Bouhfid R" first="Rachid" last="Bouhfid">Rachid Bouhfid</name><affiliation><nlm:aff id="b">Institute of Nanomaterials and Nanotechnology, MAScIR, Avenue de l’Armée Royale, Rabat,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Essassi, El Mokhtar" sort="Essassi, El Mokhtar" uniqKey="Essassi E" first="El Mokhtar" last="Essassi">El Mokhtar Essassi</name><affiliation><nlm:aff id="a">Laboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat,<country>Morocco</country></nlm:aff></affiliation><affiliation><nlm:aff id="b">Institute of Nanomaterials and Nanotechnology, MAScIR, Avenue de l’Armée Royale, Rabat,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="El Brahmi, Nabil" sort="El Brahmi, Nabil" uniqKey="El Brahmi N" first="Nabil" last="El Brahmi">Nabil El Brahmi</name><affiliation><nlm:aff id="c">Laboratoire de Chimie Organique Hétérocyclique, URAC 21, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></nlm:aff></affiliation><affiliation><nlm:aff id="d">Laboratoire de Chimie de Coordination, Équipe Dendrimères et Hétérochimie, Toulouse,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="El Ammari, Lahcen" sort="El Ammari, Lahcen" uniqKey="El Ammari L" first="Lahcen" last="El Ammari">Lahcen El Ammari</name><affiliation><nlm:aff id="e">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></nlm:aff></affiliation></author></analytic><series><title level="j">Acta Crystallographica Section E: Structure Reports Online</title><idno type="eISSN">1600-5368</idno><imprint><date when="2012">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>In the title compound, [CoCl<sub>2</sub>(C<sub>17</sub>H<sub>13</sub>N<sub>3</sub>S)<sub>2</sub>], the Co<sup>II</sup> atom exhibits a distorted octahedral coordination geometry involving two chloride ligands, one of which is split over two positions [refined site-occupancy ratio = 0.847 (18):0.153 (18)], and four N-atom donors from two 1-benzyl-2-(1,3-thiazol-4-yl)-1<italic>H</italic>-benzimidazole ligands. The two chelate rings including the Co<sup>II</sup> atom are essentially planar, the maximum deviations from the mean planes being 0.080 (2) and 0.046 (2) Å; the dihedral angle between them is 74.1 (1)°. In both ligands, the thiazole and benzimidazole rings are nearly coplanar, as indicated by the dihedral angles between their planes of 1.16 (8) and 6.29 (7)°. Each pendant benzene ring is almost perpendicular to the benzimidazole molecule to which it is attached; the dihedral angles between their planes are 75.94 (9) and 75.55 (10)°. The crystal structure is stabilized by non-classical C—H⋯Cl hydrogen bonding forming a three-dimensional network.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="iso-abbrev">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id><journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title></journal-title-group><issn pub-type="epub">1600-5368</issn><publisher><publisher-name>International Union of Crystallography</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">23476345</article-id><article-id pub-id-type="pmc">3588380</article-id><article-id pub-id-type="publisher-id">bt6860</article-id><article-id pub-id-type="doi">10.1107/S1600536812048751</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536812048751</article-id><article-categories><subj-group subj-group-type="heading"><subject>Metal-Organic Papers</subject></subj-group></article-categories><title-group><article-title>Bis[1-benzyl-2-(1,3-thiazol-4-yl)-1<italic>H</italic>-benzimidazole-κ<sup>2</sup><italic>N</italic><sup>2</sup>,<italic>N</italic><sup>3</sup>]dichloridocobalt(II)</article-title><alt-title><italic>[CoCl<sub>2</sub>(C<sub>17</sub>H<sub>13</sub>N<sub>3</sub>S)<sub>2</sub>]</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Gueddar</surname><given-names>Hicham</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="aff" rid="b">b</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><contrib contrib-type="author"><name><surname>Bouhfid</surname><given-names>Rachid</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Essassi</surname><given-names>El Mokhtar</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>El Brahmi</surname><given-names>Nabil</given-names></name><xref ref-type="aff" rid="c">c</xref><xref ref-type="aff" rid="d">d</xref></contrib><contrib contrib-type="author"><name><surname>El Ammari</surname><given-names>Lahcen</given-names></name><xref ref-type="aff" rid="e">e</xref></contrib><aff id="a"><label>a</label>Laboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat,<country>Morocco</country></aff><aff id="b"><label>b</label>Institute of Nanomaterials and Nanotechnology, MAScIR, Avenue de l’Armée Royale, Rabat,<country>Morocco</country></aff><aff id="c"><label>c</label>Laboratoire de Chimie Organique Hétérocyclique, URAC 21, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></aff><aff id="d"><label>d</label>Laboratoire de Chimie de Coordination, Équipe Dendrimères et Hétérochimie, Toulouse,<country>France</country></aff><aff id="e"><label>e</label>Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>h_gueddar@yahoo.fr</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>1</month><year>2013</year></pub-date><pub-date pub-type="epub"><day>05</day><month>12</month><year>2012</year></pub-date><pub-date pub-type="pmc-release"><day>05</day><month>12</month><year>2012</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>69</volume><issue>Pt 1</issue><issue-id pub-id-type="publisher-id">e130100</issue-id><fpage>m5</fpage><lpage>m6</lpage><history><date date-type="received"><day>16</day><month>11</month><year>2012</year></date><date date-type="accepted"><day>27</day><month>11</month><year>2012</year></date></history><permissions><copyright-statement>© Gueddar et al. 2013</copyright-statement><copyright-year>2013</copyright-year><license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/uk/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p></license></permissions><self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536812048751">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>In the title compound, [CoCl<sub>2</sub>(C<sub>17</sub>H<sub>13</sub>N<sub>3</sub>S)<sub>2</sub>], the Co<sup>II</sup> atom exhibits a distorted octahedral coordination geometry involving two chloride ligands, one of which is split over two positions [refined site-occupancy ratio = 0.847 (18):0.153 (18)], and four N-atom donors from two 1-benzyl-2-(1,3-thiazol-4-yl)-1<italic>H</italic>-benzimidazole ligands. The two chelate rings including the Co<sup>II</sup> atom are essentially planar, the maximum deviations from the mean planes being 0.080 (2) and 0.046 (2) Å; the dihedral angle between them is 74.1 (1)°. In both ligands, the thiazole and benzimidazole rings are nearly coplanar, as indicated by the dihedral angles between their planes of 1.16 (8) and 6.29 (7)°. Each pendant benzene ring is almost perpendicular to the benzimidazole molecule to which it is attached; the dihedral angles between their planes are 75.94 (9) and 75.55 (10)°. The crystal structure is stabilized by non-classical C—H⋯Cl hydrogen bonding forming a three-dimensional network.</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature
</title><p>For background of the biochemical properties of thiabendazole [2-(4′-thiazolyl)benzimidazole], see: Devereux <italic>et al.</italic> (2007<xref ref-type="bibr" rid="bb2"> ▶</xref>); Kowala <italic>et al.</italic> (1971<xref ref-type="bibr" rid="bb4"> ▶</xref>); Yan-Jua & Guang-Ganga (2009<xref ref-type="bibr" rid="bb8"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-69-000m5-scheme1.jpg" position="float"></graphic></chem-struct></p></sec><sec id="sec2"><title>Experimental
</title><sec id="sec2.1"><title></title><sec id="sec2.1.1"><title>Crystal data
</title><p><list list-type="simple"><list-item><p>[CoCl<sub>2</sub>(C<sub>17</sub>H<sub>13</sub>N<sub>3</sub>S)<sub>2</sub>]</p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 712.56</p></list-item><list-item><p>Triclinic, <inline-formula><inline-graphic xlink:href="e-69-000m5-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 10.1311 (3) Å</p></list-item><list-item><p><italic>b</italic> = 11.9582 (4) Å</p></list-item><list-item><p><italic>c</italic> = 14.2633 (5) Å</p></list-item><list-item><p>α = 76.033 (3)°</p></list-item><list-item><p>β = 75.536 (3)°</p></list-item><list-item><p>γ = 69.707 (3)°</p></list-item><list-item><p><italic>V</italic> = 1546.43 (9) Å<sup>3</sup></p></list-item><list-item><p><italic>Z</italic> = 2</p></list-item><list-item><p>Mo <italic>K</italic>α radiation</p></list-item><list-item><p>μ = 0.90 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 193 K</p></list-item><list-item><p>0.40 × 0.40 × 0.20 mm</p></list-item></list></p></sec><sec id="sec2.1.2"><title>Data collection
</title><p><list list-type="simple"><list-item><p>Bruker Kappa APEXII Quazar area-detector diffractometer</p></list-item><list-item><p>Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2009<xref ref-type="bibr" rid="bb1"> ▶</xref>) <italic>T</italic><sub>min</sub> = 0.682, <italic>T</italic><sub>max</sub> = 0.840</p></list-item><list-item><p>11578 measured reflections</p></list-item><list-item><p>6284 independent reflections</p></list-item><list-item><p>5601 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.011</p></list-item></list></p></sec><sec id="sec2.1.3"><title>Refinement
</title><p><list list-type="simple"><list-item><p><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.030</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.080</p></list-item><list-item><p><italic>S</italic> = 1.05</p></list-item><list-item><p>6284 reflections</p></list-item><list-item><p>417 parameters</p></list-item><list-item><p>H-atom parameters constrained</p></list-item><list-item><p>Δρ<sub>max</sub> = 0.95 e Å<sup>−3</sup></p></list-item><list-item><p>Δρ<sub>min</sub> = −0.68 e Å<sup>−3</sup></p></list-item></list></p></sec></sec><sec id="d5e491"><title></title><p>Data collection: <italic>APEX2</italic> (Bruker, 2009<xref ref-type="bibr" rid="bb1"> ▶</xref>); cell refinement: <italic>SAINT</italic> (Bruker, 2009<xref ref-type="bibr" rid="bb1"> ▶</xref>); data reduction: <italic>SAINT</italic>; program(s) used to solve structure: <italic>SHELXS97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb5"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb5"> ▶</xref>); molecular graphics: <italic>ORTEP-3 for Windows</italic> (Farrugia, 2012<xref ref-type="bibr" rid="bb3"> ▶</xref>); software used to prepare material for publication: <italic>PLATON</italic> (Spek, 2009<xref ref-type="bibr" rid="bb6"> ▶</xref>) and <italic>publCIF</italic> (Westrip, 2010<xref ref-type="bibr" rid="bb7"> ▶</xref>).</p></sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data"><media xlink:href="e-69-000m5-sup1.cif" mimetype="text" mime-subtype="plain"><caption><p>Click here for additional data file.</p></caption></media><p>Crystal structure: contains datablock(s) I, global. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536812048751/bt6860sup1.cif">10.1107/S1600536812048751/bt6860sup1.cif</ext-link></p><media xlink:href="e-69-000m5-sup1.cif" xlink:type="simple" id="d34e187" position="anchor" mimetype="text" mime-subtype="plain"></media></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-69-000m5-Isup2.hkl" mimetype="text" mime-subtype="plain"><caption><p>Click here for additional data file.</p></caption></media><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S1600536812048751/bt6860Isup2.hkl">10.1107/S1600536812048751/bt6860Isup2.hkl</ext-link></p><media xlink:href="e-69-000m5-Isup2.hkl" xlink:type="simple" id="d34e194" position="anchor" mimetype="text" mime-subtype="plain"></media></supplementary-material><supplementary-material content-type="local-data"><p>Additional supplementary materials: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?bt6860&file=bt6860sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?bt6860sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?bt6860&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><fn-group><fn id="fnu1"><p>Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsup?bt6860">BT6860</ext-link>).</p></fn></fn-group><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>Comment </title><p>The thiabendazole or (2-(4'-thiazolyl)benzimidazole), is an antimicrobial drug
belonging to the benzimidazole derivatives which are ubiquitous in biology and
biomedicine (Devereux <italic>et al.</italic> 2007), Beside its biological
properties,
thiabendazole is an effective ligand to coordinate transition metal ions
(Kowala <italic>et al.</italic>, 1971; Yan-Jua and Guang-Ganga, 2009).</p><p>The crystal structure of the title compound, show that the Co<sup>II</sup> ion adopts a
distorted octahedral coordination arising from two bidentate ligands and a two
Cl<sup>-</sup> anion of which one (Cl2) is splited over two positions (Cl2a and Cl2b)
and four nitrogen donors from the ligands. Indeed, the refined occupancy rate
of Cl2a and Cl2b sites shows that the first is occupied at 95 (2) % and the
remainder in the second site respectively (Fig.1). The two heterocyclic
ligands (S1N1C1C2C3) and (N2N3C4 to C10); (S2N4C18C1920) and (N5N6C21 TO C27)
are nearly coplanar with dihedral angles between them of 1.16 (8) ° and
6.26 (9)° respectively. The dihedral angle between the both thiabendazole
molecules surrounding the cobalt atom is of 74.1 (1)°. Each benzene ring (C12
to C17 and C29 to C34) is virtually perpendicular to the benzimidazole
molecule (N2N3C5 to C10 and N5N6C21 to C27) to which it is fixed and the
dihedral angle between them is 75.94 (9) for the first system and 75.55 (10) for
the second.</p><p>The crystal strucrure is further stabilized by an intermolecular C—H···Cl no
classic hydrogen bonds (Table 2).</p></sec><sec id="experimental"><title>Experimental </title><p>Thiabendazole (1.22 g, 6.02 mmol) was dissolved in 20 ml of ethanol, and
CoCl<sub>2</sub>.6H<sub>2</sub>O (0.48 g, 3.02 mmol) dissolved in 1 ml of water were added.
After 3 days of stirring at room temperature, a single-crystal precipitated
and was separated by filtration and dried at 333 K for 24 h.</p></sec><sec id="refinement"><title>Refinement </title><p>The highest peak (2.04) and the deepest hole (-1.02) in the final Fourier map
are at 0.92 Å and 0.65 Å from Cl2. The refinement of the structure in the
space group P1 with a twinning model has not led to the desired result. The
splitting of one chlorine position (Cl2) in the centrosymmetric group and the
refinement of the occupancy rate of each position has led to a slight
improvement of the refinement and there is no longer remains electronic
density near the chlorine. Indeed, the refined occupancy rate of Cl2a and Cl2b
sites shows that the first is occupied at 91.8 (2) % and the remainder in the
second site respectively. Now, the highest peak (O.95) and the deepest hole
(-0.68) in the final Fourier map are at 0.82 Å and 0.68 Å from Co1. H
atoms were located in a difference map and treated as riding with N—H = 0.86 Å, C—H = 0.93 Å (aromatic), and C—H = 0.97 Å (methylene). with
<italic>U</italic><sub>iso</sub>(H) = 1.2 <italic>U</italic><sub>eq</sub> (aromatic, methylene).</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.</p></caption><graphic xlink:href="e-69-000m5-fig1"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e124"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">[CoCl<sub>2</sub>(C<sub>17</sub>H<sub>13</sub>N<sub>3</sub>S)<sub>2</sub>]</td><td rowspan="1" colspan="1"><italic>Z</italic> = 2</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 712.56</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 730</td></tr><tr><td rowspan="1" colspan="1">Triclinic, <italic>P</italic>1</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.530 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Hall symbol: -p 1</td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation, λ = 0.71073 Å</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 10.1311 (3) Å</td><td rowspan="1" colspan="1">Cell parameters from 6245 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 11.9582 (4) Å</td><td rowspan="1" colspan="1">θ = 5.1–26.4°</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 14.2633 (5) Å</td><td rowspan="1" colspan="1">µ = 0.90 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">α = 76.033 (3)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 193 K</td></tr><tr><td rowspan="1" colspan="1">β = 75.536 (3)°</td><td rowspan="1" colspan="1">Block, pink</td></tr><tr><td rowspan="1" colspan="1">γ = 69.707 (3)°</td><td rowspan="1" colspan="1">0.40 × 0.40 × 0.20 mm</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1546.43 (9) Å<sup>3</sup></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e264"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">Bruker Kappa APEXII Quazar area-detector diffractometer</td><td rowspan="1" colspan="1">6284 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: microfocus sealed tube</td><td rowspan="1" colspan="1">5601 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">Multilayer optics monochromator</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.011</td></tr><tr><td rowspan="1" colspan="1">φ and ω scans</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 26.4°, θ<sub>min</sub> = 5.1°</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2009)</td><td rowspan="1" colspan="1"><italic>h</italic> = −12→11</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.682, <italic>T</italic><sub>max</sub> = 0.840</td><td rowspan="1" colspan="1"><italic>k</italic> = −14→14</td></tr><tr><td rowspan="1" colspan="1">11578 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −17→16</td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e381"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic><sup>2</sup></td><td rowspan="1" colspan="1">Secondary atom site location: difference Fourier map</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.030</td><td rowspan="1" colspan="1">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.080</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0362<italic>P</italic>)<sup>2</sup> + 1.3427<italic>P</italic>] where <italic>P</italic> = (<italic>F</italic><sub>o</sub><sup>2</sup> + 2<italic>F</italic><sub>c</sub><sup>2</sup>)/3</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.05</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.001</td></tr><tr><td rowspan="1" colspan="1">6284 reflections</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.95 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">417 parameters</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.68 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">0 restraints</td><td rowspan="1" colspan="1">Extinction correction: <italic>SHELXL97</italic> (Sheldrick, 2008), Fc<sup>*</sup>=kFc[1+0.001xFc<sup>2</sup>λ<sup>3</sup>/sin(2θ)]<sup>-1/4</sup></td></tr><tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td><td rowspan="1" colspan="1">Extinction coefficient: 0.0040 (5)</td></tr></table></table-wrap></sec><sec id="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e562"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.</td></tr><tr><td rowspan="1" colspan="1">Refinement. Refinement of <italic>F</italic><sup>2</sup> against all reflections. The weighted <italic>R</italic>-factor
<italic>wR</italic> and goodness of fit <italic>S</italic> are based on <italic>F</italic><sup>2</sup>, conventional
<italic>R</italic>-factors <italic>R</italic> are based on <italic>F</italic>, with <italic>F</italic> set to zero for
negative <italic>F</italic><sup>2</sup>. The threshold expression of <italic>F</italic><sup>2</sup> >
2σ(<italic>F</italic><sup>2</sup>) is used only for calculating <italic>R</italic>-factors(gt) <italic>etc</italic>.
and is not relevant to the choice of reflections for refinement.
<italic>R</italic>-factors based on <italic>F</italic><sup>2</sup> are statistically about twice as large
as those based on <italic>F</italic>, and <italic>R</italic>- factors based on all data will be
even larger.</td></tr></table></table-wrap></sec><sec id="tablewrapcoords"><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e661"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"><italic>x</italic></td><td rowspan="1" colspan="1"><italic>y</italic></td><td rowspan="1" colspan="1"><italic>z</italic></td><td rowspan="1" colspan="1"><italic>U</italic><sub>iso</sub>*/<italic>U</italic><sub>eq</sub></td><td rowspan="1" colspan="1">Occ. (<1)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.6603 (2)</td><td rowspan="1" colspan="1">0.37010 (19)</td><td rowspan="1" colspan="1">0.43804 (14)</td><td rowspan="1" colspan="1">0.0281 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">0.6306</td><td rowspan="1" colspan="1">0.4540</td><td rowspan="1" colspan="1">0.4409</td><td rowspan="1" colspan="1">0.034*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.7805 (2)</td><td rowspan="1" colspan="1">0.1569 (2)</td><td rowspan="1" colspan="1">0.44040 (15)</td><td rowspan="1" colspan="1">0.0327 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.8419</td><td rowspan="1" colspan="1">0.0759</td><td rowspan="1" colspan="1">0.4434</td><td rowspan="1" colspan="1">0.039*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.64845 (19)</td><td rowspan="1" colspan="1">0.19650 (17)</td><td rowspan="1" colspan="1">0.41692 (13)</td><td rowspan="1" colspan="1">0.0223 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.56253 (19)</td><td rowspan="1" colspan="1">0.13517 (16)</td><td rowspan="1" colspan="1">0.39322 (13)</td><td rowspan="1" colspan="1">0.0214 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.3835 (2)</td><td rowspan="1" colspan="1">0.11633 (17)</td><td rowspan="1" colspan="1">0.35002 (13)</td><td rowspan="1" colspan="1">0.0236 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.2527 (2)</td><td rowspan="1" colspan="1">0.13165 (19)</td><td rowspan="1" colspan="1">0.32592 (14)</td><td rowspan="1" colspan="1">0.0289 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6</td><td rowspan="1" colspan="1">0.1811</td><td rowspan="1" colspan="1">0.2082</td><td rowspan="1" colspan="1">0.3214</td><td rowspan="1" colspan="1">0.035*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.2314 (3)</td><td rowspan="1" colspan="1">0.0305 (2)</td><td rowspan="1" colspan="1">0.30877 (15)</td><td rowspan="1" colspan="1">0.0366 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7</td><td rowspan="1" colspan="1">0.1435</td><td rowspan="1" colspan="1">0.0381</td><td rowspan="1" colspan="1">0.2918</td><td rowspan="1" colspan="1">0.044*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.3360 (3)</td><td rowspan="1" colspan="1">−0.0824 (2)</td><td rowspan="1" colspan="1">0.31586 (16)</td><td rowspan="1" colspan="1">0.0388 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H8</td><td rowspan="1" colspan="1">0.3176</td><td rowspan="1" colspan="1">−0.1493</td><td rowspan="1" colspan="1">0.3027</td><td rowspan="1" colspan="1">0.047*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.4642 (3)</td><td rowspan="1" colspan="1">−0.09957 (19)</td><td rowspan="1" colspan="1">0.34126 (15)</td><td rowspan="1" colspan="1">0.0346 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9</td><td rowspan="1" colspan="1">0.5349</td><td rowspan="1" colspan="1">−0.1765</td><td rowspan="1" colspan="1">0.3467</td><td rowspan="1" colspan="1">0.041*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.4850 (2)</td><td rowspan="1" colspan="1">0.00220 (17)</td><td rowspan="1" colspan="1">0.35870 (13)</td><td rowspan="1" colspan="1">0.0260 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.7263 (2)</td><td rowspan="1" colspan="1">−0.08140 (17)</td><td rowspan="1" colspan="1">0.40841 (15)</td><td rowspan="1" colspan="1">0.0301 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11A</td><td rowspan="1" colspan="1">0.7035</td><td rowspan="1" colspan="1">−0.1588</td><td rowspan="1" colspan="1">0.4266</td><td rowspan="1" colspan="1">0.036*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11B</td><td rowspan="1" colspan="1">0.7546</td><td rowspan="1" colspan="1">−0.0691</td><td rowspan="1" colspan="1">0.4659</td><td rowspan="1" colspan="1">0.036*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.8512 (2)</td><td rowspan="1" colspan="1">−0.09147 (16)</td><td rowspan="1" colspan="1">0.32447 (13)</td><td rowspan="1" colspan="1">0.0226 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.9687 (2)</td><td rowspan="1" colspan="1">−0.19429 (17)</td><td rowspan="1" colspan="1">0.33241 (15)</td><td rowspan="1" colspan="1">0.0292 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.9665</td><td rowspan="1" colspan="1">−0.2561</td><td rowspan="1" colspan="1">0.3884</td><td rowspan="1" colspan="1">0.035*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">1.0883 (2)</td><td rowspan="1" colspan="1">−0.20696 (19)</td><td rowspan="1" colspan="1">0.25942 (18)</td><td rowspan="1" colspan="1">0.0364 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H14</td><td rowspan="1" colspan="1">1.1685</td><td rowspan="1" colspan="1">−0.2774</td><td rowspan="1" colspan="1">0.2651</td><td rowspan="1" colspan="1">0.044*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">1.0916 (2)</td><td rowspan="1" colspan="1">−0.11754 (19)</td><td rowspan="1" colspan="1">0.17831 (17)</td><td rowspan="1" colspan="1">0.0345 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15</td><td rowspan="1" colspan="1">1.1748</td><td rowspan="1" colspan="1">−0.1259</td><td rowspan="1" colspan="1">0.1285</td><td rowspan="1" colspan="1">0.041*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.9753 (2)</td><td rowspan="1" colspan="1">−0.01644 (18)</td><td rowspan="1" colspan="1">0.16905 (15)</td><td rowspan="1" colspan="1">0.0299 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16</td><td rowspan="1" colspan="1">0.9776</td><td rowspan="1" colspan="1">0.0445</td><td rowspan="1" colspan="1">0.1124</td><td rowspan="1" colspan="1">0.036*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.8548 (2)</td><td rowspan="1" colspan="1">−0.00304 (17)</td><td rowspan="1" colspan="1">0.24201 (14)</td><td rowspan="1" colspan="1">0.0256 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17</td><td rowspan="1" colspan="1">0.7744</td><td rowspan="1" colspan="1">0.0671</td><td rowspan="1" colspan="1">0.2355</td><td rowspan="1" colspan="1">0.031*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.0728 (2)</td><td rowspan="1" colspan="1">0.47264 (19)</td><td rowspan="1" colspan="1">0.31938 (17)</td><td rowspan="1" colspan="1">0.0328 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18</td><td rowspan="1" colspan="1">0.0335</td><td rowspan="1" colspan="1">0.4909</td><td rowspan="1" colspan="1">0.3837</td><td rowspan="1" colspan="1">0.039*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.1212 (2)</td><td rowspan="1" colspan="1">0.4361 (2)</td><td rowspan="1" colspan="1">0.15296 (17)</td><td rowspan="1" colspan="1">0.0370 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19</td><td rowspan="1" colspan="1">0.1224</td><td rowspan="1" colspan="1">0.4249</td><td rowspan="1" colspan="1">0.0890</td><td rowspan="1" colspan="1">0.044*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.2387 (2)</td><td rowspan="1" colspan="1">0.41930 (17)</td><td rowspan="1" colspan="1">0.18986 (15)</td><td rowspan="1" colspan="1">0.0258 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">0.3907 (2)</td><td rowspan="1" colspan="1">0.38422 (16)</td><td rowspan="1" colspan="1">0.14785 (13)</td><td rowspan="1" colspan="1">0.0221 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C22</td><td rowspan="1" colspan="1">0.61612 (19)</td><td rowspan="1" colspan="1">0.34029 (15)</td><td rowspan="1" colspan="1">0.14499 (13)</td><td rowspan="1" colspan="1">0.0211 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C23</td><td rowspan="1" colspan="1">0.7512 (2)</td><td rowspan="1" colspan="1">0.31937 (16)</td><td rowspan="1" colspan="1">0.16493 (14)</td><td rowspan="1" colspan="1">0.0251 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H23</td><td rowspan="1" colspan="1">0.7639</td><td rowspan="1" colspan="1">0.3202</td><td rowspan="1" colspan="1">0.2285</td><td rowspan="1" colspan="1">0.030*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C24</td><td rowspan="1" colspan="1">0.8657 (2)</td><td rowspan="1" colspan="1">0.29749 (18)</td><td rowspan="1" colspan="1">0.08846 (16)</td><td rowspan="1" colspan="1">0.0314 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H24</td><td rowspan="1" colspan="1">0.9593</td><td rowspan="1" colspan="1">0.2821</td><td rowspan="1" colspan="1">0.0999</td><td rowspan="1" colspan="1">0.038*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C25</td><td rowspan="1" colspan="1">0.8473 (2)</td><td rowspan="1" colspan="1">0.29740 (19)</td><td rowspan="1" colspan="1">−0.00575 (16)</td><td rowspan="1" colspan="1">0.0349 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H25</td><td rowspan="1" colspan="1">0.9291</td><td rowspan="1" colspan="1">0.2818</td><td rowspan="1" colspan="1">−0.0565</td><td rowspan="1" colspan="1">0.042*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C26</td><td rowspan="1" colspan="1">0.7144 (2)</td><td rowspan="1" colspan="1">0.31922 (18)</td><td rowspan="1" colspan="1">−0.02687 (15)</td><td rowspan="1" colspan="1">0.0308 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H26</td><td rowspan="1" colspan="1">0.7020</td><td rowspan="1" colspan="1">0.3200</td><td rowspan="1" colspan="1">−0.0909</td><td rowspan="1" colspan="1">0.037*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C27</td><td rowspan="1" colspan="1">0.5995 (2)</td><td rowspan="1" colspan="1">0.34003 (16)</td><td rowspan="1" colspan="1">0.05055 (14)</td><td rowspan="1" colspan="1">0.0236 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C28</td><td rowspan="1" colspan="1">0.3882 (2)</td><td rowspan="1" colspan="1">0.37895 (18)</td><td rowspan="1" colspan="1">−0.02866 (14)</td><td rowspan="1" colspan="1">0.0287 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H28A</td><td rowspan="1" colspan="1">0.4548</td><td rowspan="1" colspan="1">0.3952</td><td rowspan="1" colspan="1">−0.0904</td><td rowspan="1" colspan="1">0.034*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H28B</td><td rowspan="1" colspan="1">0.3003</td><td rowspan="1" colspan="1">0.4492</td><td rowspan="1" colspan="1">−0.0273</td><td rowspan="1" colspan="1">0.034*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C29</td><td rowspan="1" colspan="1">0.3500 (2)</td><td rowspan="1" colspan="1">0.26816 (18)</td><td rowspan="1" colspan="1">−0.02967 (14)</td><td rowspan="1" colspan="1">0.0268 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C30</td><td rowspan="1" colspan="1">0.3025 (3)</td><td rowspan="1" colspan="1">0.2664 (2)</td><td rowspan="1" colspan="1">−0.11220 (17)</td><td rowspan="1" colspan="1">0.0370 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H30</td><td rowspan="1" colspan="1">0.2987</td><td rowspan="1" colspan="1">0.3317</td><td rowspan="1" colspan="1">−0.1658</td><td rowspan="1" colspan="1">0.044*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C31</td><td rowspan="1" colspan="1">0.2607 (3)</td><td rowspan="1" colspan="1">0.1699 (2)</td><td rowspan="1" colspan="1">−0.11673 (18)</td><td rowspan="1" colspan="1">0.0454 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H31</td><td rowspan="1" colspan="1">0.2260</td><td rowspan="1" colspan="1">0.1699</td><td rowspan="1" colspan="1">−0.1728</td><td rowspan="1" colspan="1">0.055*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C32</td><td rowspan="1" colspan="1">0.2692 (3)</td><td rowspan="1" colspan="1">0.0738 (2)</td><td rowspan="1" colspan="1">−0.04062 (18)</td><td rowspan="1" colspan="1">0.0462 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H32</td><td rowspan="1" colspan="1">0.2412</td><td rowspan="1" colspan="1">0.0071</td><td rowspan="1" colspan="1">−0.0442</td><td rowspan="1" colspan="1">0.055*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C33</td><td rowspan="1" colspan="1">0.3181 (3)</td><td rowspan="1" colspan="1">0.0742 (2)</td><td rowspan="1" colspan="1">0.04040 (19)</td><td rowspan="1" colspan="1">0.0531 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H33</td><td rowspan="1" colspan="1">0.3247</td><td rowspan="1" colspan="1">0.0075</td><td rowspan="1" colspan="1">0.0929</td><td rowspan="1" colspan="1">0.064*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C34</td><td rowspan="1" colspan="1">0.3580 (3)</td><td rowspan="1" colspan="1">0.1720 (2)</td><td rowspan="1" colspan="1">0.04607 (17)</td><td rowspan="1" colspan="1">0.0441 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H34</td><td rowspan="1" colspan="1">0.3912</td><td rowspan="1" colspan="1">0.1721</td><td rowspan="1" colspan="1">0.1027</td><td rowspan="1" colspan="1">0.053*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.58202 (16)</td><td rowspan="1" colspan="1">0.31923 (14)</td><td rowspan="1" colspan="1">0.41412 (11)</td><td rowspan="1" colspan="1">0.0224 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.43504 (16)</td><td rowspan="1" colspan="1">0.19849 (13)</td><td rowspan="1" colspan="1">0.37231 (11)</td><td rowspan="1" colspan="1">0.0208 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.59824 (17)</td><td rowspan="1" colspan="1">0.01613 (14)</td><td rowspan="1" colspan="1">0.38752 (12)</td><td rowspan="1" colspan="1">0.0253 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.20969 (16)</td><td rowspan="1" colspan="1">0.43936 (14)</td><td rowspan="1" colspan="1">0.28531 (12)</td><td rowspan="1" colspan="1">0.0253 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.48317 (16)</td><td rowspan="1" colspan="1">0.36795 (13)</td><td rowspan="1" colspan="1">0.20426 (11)</td><td rowspan="1" colspan="1">0.0208 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N6</td><td rowspan="1" colspan="1">0.45439 (17)</td><td rowspan="1" colspan="1">0.36890 (14)</td><td rowspan="1" colspan="1">0.05423 (11)</td><td rowspan="1" colspan="1">0.0240 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.82050 (6)</td><td rowspan="1" colspan="1">0.27380 (6)</td><td rowspan="1" colspan="1">0.46385 (4)</td><td rowspan="1" colspan="1">0.03746 (14)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S2</td><td rowspan="1" colspan="1">−0.02965 (6)</td><td rowspan="1" colspan="1">0.48051 (6)</td><td rowspan="1" colspan="1">0.23841 (5)</td><td rowspan="1" colspan="1">0.04537 (16)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Cl1</td><td rowspan="1" colspan="1">0.42867 (5)</td><td rowspan="1" colspan="1">0.58768 (4)</td><td rowspan="1" colspan="1">0.30588 (4)</td><td rowspan="1" colspan="1">0.03220 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Cl2A</td><td rowspan="1" colspan="1">0.23855 (17)</td><td rowspan="1" colspan="1">0.40676 (12)</td><td rowspan="1" colspan="1">0.5152 (2)</td><td rowspan="1" colspan="1">0.0232 (5)</td><td rowspan="1" colspan="1">0.847 (18)</td></tr><tr><td rowspan="1" colspan="1">Cl2B</td><td rowspan="1" colspan="1">0.215 (2)</td><td rowspan="1" colspan="1">0.444 (4)</td><td rowspan="1" colspan="1">0.485 (2)</td><td rowspan="1" colspan="1">0.060 (6)</td><td rowspan="1" colspan="1">0.153 (18)</td></tr><tr><td rowspan="1" colspan="1">Co1</td><td rowspan="1" colspan="1">0.39016 (2)</td><td rowspan="1" colspan="1">0.39444 (2)</td><td rowspan="1" colspan="1">0.355093 (18)</td><td rowspan="1" colspan="1">0.02006 (8)</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapadps"><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e1632"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"><italic>U</italic><sup>11</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>22</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>33</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>12</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>13</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>23</sup></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0262 (9)</td><td rowspan="1" colspan="1">0.0369 (11)</td><td rowspan="1" colspan="1">0.0278 (10)</td><td rowspan="1" colspan="1">−0.0143 (8)</td><td rowspan="1" colspan="1">−0.0031 (8)</td><td rowspan="1" colspan="1">−0.0125 (8)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0277 (10)</td><td rowspan="1" colspan="1">0.0361 (11)</td><td rowspan="1" colspan="1">0.0330 (11)</td><td rowspan="1" colspan="1">−0.0096 (8)</td><td rowspan="1" colspan="1">−0.0084 (8)</td><td rowspan="1" colspan="1">−0.0009 (9)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0231 (9)</td><td rowspan="1" colspan="1">0.0251 (9)</td><td rowspan="1" colspan="1">0.0182 (8)</td><td rowspan="1" colspan="1">−0.0092 (7)</td><td rowspan="1" colspan="1">−0.0003 (7)</td><td rowspan="1" colspan="1">−0.0038 (7)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0232 (9)</td><td rowspan="1" colspan="1">0.0223 (9)</td><td rowspan="1" colspan="1">0.0179 (8)</td><td rowspan="1" colspan="1">−0.0088 (7)</td><td rowspan="1" colspan="1">0.0017 (7)</td><td rowspan="1" colspan="1">−0.0049 (7)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0313 (10)</td><td rowspan="1" colspan="1">0.0254 (9)</td><td rowspan="1" colspan="1">0.0181 (8)</td><td rowspan="1" colspan="1">−0.0162 (8)</td><td rowspan="1" colspan="1">0.0022 (7)</td><td rowspan="1" colspan="1">−0.0066 (7)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0363 (11)</td><td rowspan="1" colspan="1">0.0312 (10)</td><td rowspan="1" colspan="1">0.0258 (9)</td><td rowspan="1" colspan="1">−0.0186 (9)</td><td rowspan="1" colspan="1">−0.0055 (8)</td><td rowspan="1" colspan="1">−0.0046 (8)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0499 (13)</td><td rowspan="1" colspan="1">0.0449 (13)</td><td rowspan="1" colspan="1">0.0290 (10)</td><td rowspan="1" colspan="1">−0.0316 (11)</td><td rowspan="1" colspan="1">−0.0084 (9)</td><td rowspan="1" colspan="1">−0.0051 (9)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0610 (15)</td><td rowspan="1" colspan="1">0.0334 (11)</td><td rowspan="1" colspan="1">0.0332 (11)</td><td rowspan="1" colspan="1">−0.0302 (11)</td><td rowspan="1" colspan="1">−0.0008 (10)</td><td rowspan="1" colspan="1">−0.0107 (9)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0485 (13)</td><td rowspan="1" colspan="1">0.0253 (10)</td><td rowspan="1" colspan="1">0.0311 (10)</td><td rowspan="1" colspan="1">−0.0185 (9)</td><td rowspan="1" colspan="1">0.0061 (9)</td><td rowspan="1" colspan="1">−0.0100 (8)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0327 (10)</td><td rowspan="1" colspan="1">0.0243 (9)</td><td rowspan="1" colspan="1">0.0213 (9)</td><td rowspan="1" colspan="1">−0.0140 (8)</td><td rowspan="1" colspan="1">0.0049 (7)</td><td rowspan="1" colspan="1">−0.0070 (7)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0350 (11)</td><td rowspan="1" colspan="1">0.0207 (9)</td><td rowspan="1" colspan="1">0.0263 (10)</td><td rowspan="1" colspan="1">−0.0045 (8)</td><td rowspan="1" colspan="1">−0.0004 (8)</td><td rowspan="1" colspan="1">0.0001 (7)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0255 (9)</td><td rowspan="1" colspan="1">0.0199 (9)</td><td rowspan="1" colspan="1">0.0240 (9)</td><td rowspan="1" colspan="1">−0.0066 (7)</td><td rowspan="1" colspan="1">−0.0052 (7)</td><td rowspan="1" colspan="1">−0.0066 (7)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0319 (10)</td><td rowspan="1" colspan="1">0.0217 (9)</td><td rowspan="1" colspan="1">0.0356 (11)</td><td rowspan="1" colspan="1">−0.0061 (8)</td><td rowspan="1" colspan="1">−0.0129 (8)</td><td rowspan="1" colspan="1">−0.0041 (8)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0229 (10)</td><td rowspan="1" colspan="1">0.0282 (10)</td><td rowspan="1" colspan="1">0.0582 (14)</td><td rowspan="1" colspan="1">−0.0025 (8)</td><td rowspan="1" colspan="1">−0.0070 (9)</td><td rowspan="1" colspan="1">−0.0161 (10)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0291 (10)</td><td rowspan="1" colspan="1">0.0311 (11)</td><td rowspan="1" colspan="1">0.0464 (12)</td><td rowspan="1" colspan="1">−0.0140 (9)</td><td rowspan="1" colspan="1">0.0067 (9)</td><td rowspan="1" colspan="1">−0.0197 (9)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.0362 (11)</td><td rowspan="1" colspan="1">0.0258 (10)</td><td rowspan="1" colspan="1">0.0290 (10)</td><td rowspan="1" colspan="1">−0.0139 (8)</td><td rowspan="1" colspan="1">0.0027 (8)</td><td rowspan="1" colspan="1">−0.0092 (8)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.0286 (10)</td><td rowspan="1" colspan="1">0.0204 (9)</td><td rowspan="1" colspan="1">0.0255 (9)</td><td rowspan="1" colspan="1">−0.0053 (7)</td><td rowspan="1" colspan="1">−0.0027 (8)</td><td rowspan="1" colspan="1">−0.0051 (7)</td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.0215 (9)</td><td rowspan="1" colspan="1">0.0289 (10)</td><td rowspan="1" colspan="1">0.0474 (12)</td><td rowspan="1" colspan="1">−0.0078 (8)</td><td rowspan="1" colspan="1">−0.0027 (9)</td><td rowspan="1" colspan="1">−0.0087 (9)</td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.0327 (11)</td><td rowspan="1" colspan="1">0.0465 (13)</td><td rowspan="1" colspan="1">0.0368 (11)</td><td rowspan="1" colspan="1">−0.0206 (10)</td><td rowspan="1" colspan="1">−0.0141 (9)</td><td rowspan="1" colspan="1">0.0044 (10)</td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.0253 (9)</td><td rowspan="1" colspan="1">0.0224 (9)</td><td rowspan="1" colspan="1">0.0333 (10)</td><td rowspan="1" colspan="1">−0.0118 (7)</td><td rowspan="1" colspan="1">−0.0085 (8)</td><td rowspan="1" colspan="1">−0.0014 (8)</td></tr><tr><td rowspan="1" colspan="1">C21</td><td rowspan="1" colspan="1">0.0259 (9)</td><td rowspan="1" colspan="1">0.0180 (8)</td><td rowspan="1" colspan="1">0.0262 (9)</td><td rowspan="1" colspan="1">−0.0109 (7)</td><td rowspan="1" colspan="1">−0.0057 (7)</td><td rowspan="1" colspan="1">−0.0034 (7)</td></tr><tr><td rowspan="1" colspan="1">C22</td><td rowspan="1" colspan="1">0.0242 (9)</td><td rowspan="1" colspan="1">0.0151 (8)</td><td rowspan="1" colspan="1">0.0238 (9)</td><td rowspan="1" colspan="1">−0.0072 (7)</td><td rowspan="1" colspan="1">−0.0014 (7)</td><td rowspan="1" colspan="1">−0.0040 (7)</td></tr><tr><td rowspan="1" colspan="1">C23</td><td rowspan="1" colspan="1">0.0246 (9)</td><td rowspan="1" colspan="1">0.0215 (9)</td><td rowspan="1" colspan="1">0.0281 (9)</td><td rowspan="1" colspan="1">−0.0078 (7)</td><td rowspan="1" colspan="1">−0.0034 (7)</td><td rowspan="1" colspan="1">−0.0029 (7)</td></tr><tr><td rowspan="1" colspan="1">C24</td><td rowspan="1" colspan="1">0.0247 (10)</td><td rowspan="1" colspan="1">0.0253 (10)</td><td rowspan="1" colspan="1">0.0404 (11)</td><td rowspan="1" colspan="1">−0.0075 (8)</td><td rowspan="1" colspan="1">−0.0003 (8)</td><td rowspan="1" colspan="1">−0.0047 (8)</td></tr><tr><td rowspan="1" colspan="1">C25</td><td rowspan="1" colspan="1">0.0350 (11)</td><td rowspan="1" colspan="1">0.0267 (10)</td><td rowspan="1" colspan="1">0.0353 (11)</td><td rowspan="1" colspan="1">−0.0078 (8)</td><td rowspan="1" colspan="1">0.0089 (9)</td><td rowspan="1" colspan="1">−0.0097 (8)</td></tr><tr><td rowspan="1" colspan="1">C26</td><td rowspan="1" colspan="1">0.0409 (11)</td><td rowspan="1" colspan="1">0.0238 (9)</td><td rowspan="1" colspan="1">0.0269 (10)</td><td rowspan="1" colspan="1">−0.0107 (8)</td><td rowspan="1" colspan="1">0.0016 (8)</td><td rowspan="1" colspan="1">−0.0093 (8)</td></tr><tr><td rowspan="1" colspan="1">C27</td><td rowspan="1" colspan="1">0.0319 (10)</td><td rowspan="1" colspan="1">0.0150 (8)</td><td rowspan="1" colspan="1">0.0249 (9)</td><td rowspan="1" colspan="1">−0.0093 (7)</td><td rowspan="1" colspan="1">−0.0033 (7)</td><td rowspan="1" colspan="1">−0.0037 (7)</td></tr><tr><td rowspan="1" colspan="1">C28</td><td rowspan="1" colspan="1">0.0415 (11)</td><td rowspan="1" colspan="1">0.0254 (10)</td><td rowspan="1" colspan="1">0.0246 (9)</td><td rowspan="1" colspan="1">−0.0142 (8)</td><td rowspan="1" colspan="1">−0.0125 (8)</td><td rowspan="1" colspan="1">−0.0015 (7)</td></tr><tr><td rowspan="1" colspan="1">C29</td><td rowspan="1" colspan="1">0.0308 (10)</td><td rowspan="1" colspan="1">0.0275 (10)</td><td rowspan="1" colspan="1">0.0268 (9)</td><td rowspan="1" colspan="1">−0.0125 (8)</td><td rowspan="1" colspan="1">−0.0048 (8)</td><td rowspan="1" colspan="1">−0.0080 (8)</td></tr><tr><td rowspan="1" colspan="1">C30</td><td rowspan="1" colspan="1">0.0461 (13)</td><td rowspan="1" colspan="1">0.0391 (12)</td><td rowspan="1" colspan="1">0.0344 (11)</td><td rowspan="1" colspan="1">−0.0170 (10)</td><td rowspan="1" colspan="1">−0.0156 (10)</td><td rowspan="1" colspan="1">−0.0072 (9)</td></tr><tr><td rowspan="1" colspan="1">C31</td><td rowspan="1" colspan="1">0.0549 (15)</td><td rowspan="1" colspan="1">0.0564 (15)</td><td rowspan="1" colspan="1">0.0425 (13)</td><td rowspan="1" colspan="1">−0.0287 (12)</td><td rowspan="1" colspan="1">−0.0153 (11)</td><td rowspan="1" colspan="1">−0.0164 (11)</td></tr><tr><td rowspan="1" colspan="1">C32</td><td rowspan="1" colspan="1">0.0615 (16)</td><td rowspan="1" colspan="1">0.0519 (15)</td><td rowspan="1" colspan="1">0.0437 (13)</td><td rowspan="1" colspan="1">−0.0398 (13)</td><td rowspan="1" colspan="1">0.0016 (11)</td><td rowspan="1" colspan="1">−0.0201 (11)</td></tr><tr><td rowspan="1" colspan="1">C33</td><td rowspan="1" colspan="1">0.094 (2)</td><td rowspan="1" colspan="1">0.0456 (14)</td><td rowspan="1" colspan="1">0.0383 (13)</td><td rowspan="1" colspan="1">−0.0476 (15)</td><td rowspan="1" colspan="1">−0.0124 (13)</td><td rowspan="1" colspan="1">−0.0008 (11)</td></tr><tr><td rowspan="1" colspan="1">C34</td><td rowspan="1" colspan="1">0.0774 (18)</td><td rowspan="1" colspan="1">0.0400 (13)</td><td rowspan="1" colspan="1">0.0310 (11)</td><td rowspan="1" colspan="1">−0.0352 (13)</td><td rowspan="1" colspan="1">−0.0170 (11)</td><td rowspan="1" colspan="1">−0.0023 (9)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0217 (7)</td><td rowspan="1" colspan="1">0.0267 (8)</td><td rowspan="1" colspan="1">0.0225 (7)</td><td rowspan="1" colspan="1">−0.0105 (6)</td><td rowspan="1" colspan="1">−0.0014 (6)</td><td rowspan="1" colspan="1">−0.0094 (6)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0241 (8)</td><td rowspan="1" colspan="1">0.0209 (7)</td><td rowspan="1" colspan="1">0.0199 (7)</td><td rowspan="1" colspan="1">−0.0105 (6)</td><td rowspan="1" colspan="1">−0.0005 (6)</td><td rowspan="1" colspan="1">−0.0064 (6)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0273 (8)</td><td rowspan="1" colspan="1">0.0198 (8)</td><td rowspan="1" colspan="1">0.0264 (8)</td><td rowspan="1" colspan="1">−0.0089 (6)</td><td rowspan="1" colspan="1">0.0030 (6)</td><td rowspan="1" colspan="1">−0.0050 (6)</td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.0198 (7)</td><td rowspan="1" colspan="1">0.0219 (8)</td><td rowspan="1" colspan="1">0.0358 (9)</td><td rowspan="1" colspan="1">−0.0076 (6)</td><td rowspan="1" colspan="1">−0.0030 (6)</td><td rowspan="1" colspan="1">−0.0085 (7)</td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.0223 (7)</td><td rowspan="1" colspan="1">0.0189 (7)</td><td rowspan="1" colspan="1">0.0233 (7)</td><td rowspan="1" colspan="1">−0.0089 (6)</td><td rowspan="1" colspan="1">−0.0036 (6)</td><td rowspan="1" colspan="1">−0.0042 (6)</td></tr><tr><td rowspan="1" colspan="1">N6</td><td rowspan="1" colspan="1">0.0313 (8)</td><td rowspan="1" colspan="1">0.0212 (7)</td><td rowspan="1" colspan="1">0.0246 (8)</td><td rowspan="1" colspan="1">−0.0126 (6)</td><td rowspan="1" colspan="1">−0.0072 (6)</td><td rowspan="1" colspan="1">−0.0042 (6)</td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.0308 (3)</td><td rowspan="1" colspan="1">0.0532 (3)</td><td rowspan="1" colspan="1">0.0371 (3)</td><td rowspan="1" colspan="1">−0.0197 (2)</td><td rowspan="1" colspan="1">−0.0136 (2)</td><td rowspan="1" colspan="1">−0.0056 (2)</td></tr><tr><td rowspan="1" colspan="1">S2</td><td rowspan="1" colspan="1">0.0221 (3)</td><td rowspan="1" colspan="1">0.0555 (4)</td><td rowspan="1" colspan="1">0.0574 (4)</td><td rowspan="1" colspan="1">−0.0146 (2)</td><td rowspan="1" colspan="1">−0.0140 (2)</td><td rowspan="1" colspan="1">0.0036 (3)</td></tr><tr><td rowspan="1" colspan="1">Cl1</td><td rowspan="1" colspan="1">0.0315 (2)</td><td rowspan="1" colspan="1">0.0200 (2)</td><td rowspan="1" colspan="1">0.0489 (3)</td><td rowspan="1" colspan="1">−0.00923 (18)</td><td rowspan="1" colspan="1">−0.0090 (2)</td><td rowspan="1" colspan="1">−0.0089 (2)</td></tr><tr><td rowspan="1" colspan="1">Cl2A</td><td rowspan="1" colspan="1">0.0228 (4)</td><td rowspan="1" colspan="1">0.0248 (8)</td><td rowspan="1" colspan="1">0.0240 (7)</td><td rowspan="1" colspan="1">−0.0103 (4)</td><td rowspan="1" colspan="1">0.0029 (3)</td><td rowspan="1" colspan="1">−0.0110 (4)</td></tr><tr><td rowspan="1" colspan="1">Cl2B</td><td rowspan="1" colspan="1">0.039 (4)</td><td rowspan="1" colspan="1">0.108 (13)</td><td rowspan="1" colspan="1">0.050 (8)</td><td rowspan="1" colspan="1">−0.038 (7)</td><td rowspan="1" colspan="1">0.011 (5)</td><td rowspan="1" colspan="1">−0.041 (10)</td></tr><tr><td rowspan="1" colspan="1">Co1</td><td rowspan="1" colspan="1">0.01664 (13)</td><td rowspan="1" colspan="1">0.02009 (13)</td><td rowspan="1" colspan="1">0.02660 (14)</td><td rowspan="1" colspan="1">−0.00703 (9)</td><td rowspan="1" colspan="1">−0.00087 (9)</td><td rowspan="1" colspan="1">−0.01077 (10)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e2617"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">C1—N1</td><td rowspan="1" colspan="1">1.298 (2)</td><td rowspan="1" colspan="1">C19—S2</td><td rowspan="1" colspan="1">1.710 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—S1</td><td rowspan="1" colspan="1">1.701 (2)</td><td rowspan="1" colspan="1">C19—H19</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C1—H1</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C20—N4</td><td rowspan="1" colspan="1">1.381 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.354 (3)</td><td rowspan="1" colspan="1">C20—C21</td><td rowspan="1" colspan="1">1.456 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—S1</td><td rowspan="1" colspan="1">1.708 (2)</td><td rowspan="1" colspan="1">C21—N5</td><td rowspan="1" colspan="1">1.318 (2)</td></tr><tr><td rowspan="1" colspan="1">C2—H2</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C21—N6</td><td rowspan="1" colspan="1">1.356 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—N1</td><td rowspan="1" colspan="1">1.382 (2)</td><td rowspan="1" colspan="1">C22—N5</td><td rowspan="1" colspan="1">1.377 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.456 (3)</td><td rowspan="1" colspan="1">C22—C23</td><td rowspan="1" colspan="1">1.392 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—N2</td><td rowspan="1" colspan="1">1.317 (2)</td><td rowspan="1" colspan="1">C22—C27</td><td rowspan="1" colspan="1">1.400 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—N3</td><td rowspan="1" colspan="1">1.359 (2)</td><td rowspan="1" colspan="1">C23—C24</td><td rowspan="1" colspan="1">1.378 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—N2</td><td rowspan="1" colspan="1">1.389 (2)</td><td rowspan="1" colspan="1">C23—H23</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.392 (3)</td><td rowspan="1" colspan="1">C24—C25</td><td rowspan="1" colspan="1">1.402 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C10</td><td rowspan="1" colspan="1">1.394 (3)</td><td rowspan="1" colspan="1">C24—H24</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C6—C7</td><td rowspan="1" colspan="1">1.385 (3)</td><td rowspan="1" colspan="1">C25—C26</td><td rowspan="1" colspan="1">1.376 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—H6</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C25—H25</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.397 (3)</td><td rowspan="1" colspan="1">C26—C27</td><td rowspan="1" colspan="1">1.388 (3)</td></tr><tr><td rowspan="1" colspan="1">C7—H7</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C26—H26</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.369 (3)</td><td rowspan="1" colspan="1">C27—N6</td><td rowspan="1" colspan="1">1.379 (2)</td></tr><tr><td rowspan="1" colspan="1">C8—H8</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C28—N6</td><td rowspan="1" colspan="1">1.460 (2)</td></tr><tr><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.392 (3)</td><td rowspan="1" colspan="1">C28—C29</td><td rowspan="1" colspan="1">1.508 (3)</td></tr><tr><td rowspan="1" colspan="1">C9—H9</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C28—H28A</td><td rowspan="1" colspan="1">0.9900</td></tr><tr><td rowspan="1" colspan="1">C10—N3</td><td rowspan="1" colspan="1">1.383 (3)</td><td rowspan="1" colspan="1">C28—H28B</td><td rowspan="1" colspan="1">0.9900</td></tr><tr><td rowspan="1" colspan="1">C11—N3</td><td rowspan="1" colspan="1">1.452 (2)</td><td rowspan="1" colspan="1">C29—C34</td><td rowspan="1" colspan="1">1.370 (3)</td></tr><tr><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.502 (3)</td><td rowspan="1" colspan="1">C29—C30</td><td rowspan="1" colspan="1">1.386 (3)</td></tr><tr><td rowspan="1" colspan="1">C11—H11A</td><td rowspan="1" colspan="1">0.9900</td><td rowspan="1" colspan="1">C30—C31</td><td rowspan="1" colspan="1">1.380 (3)</td></tr><tr><td rowspan="1" colspan="1">C11—H11B</td><td rowspan="1" colspan="1">0.9900</td><td rowspan="1" colspan="1">C30—H30</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C12—C17</td><td rowspan="1" colspan="1">1.381 (3)</td><td rowspan="1" colspan="1">C31—C32</td><td rowspan="1" colspan="1">1.372 (4)</td></tr><tr><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.388 (3)</td><td rowspan="1" colspan="1">C31—H31</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C13—C14</td><td rowspan="1" colspan="1">1.376 (3)</td><td rowspan="1" colspan="1">C32—C33</td><td rowspan="1" colspan="1">1.368 (3)</td></tr><tr><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C32—H32</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.375 (3)</td><td rowspan="1" colspan="1">C33—C34</td><td rowspan="1" colspan="1">1.388 (3)</td></tr><tr><td rowspan="1" colspan="1">C14—H14</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C33—H33</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.371 (3)</td><td rowspan="1" colspan="1">C34—H34</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C15—H15</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">N1—Co1</td><td rowspan="1" colspan="1">2.1297 (15)</td></tr><tr><td rowspan="1" colspan="1">C16—C17</td><td rowspan="1" colspan="1">1.382 (3)</td><td rowspan="1" colspan="1">N2—Co1</td><td rowspan="1" colspan="1">2.1901 (15)</td></tr><tr><td rowspan="1" colspan="1">C16—H16</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">N4—Co1</td><td rowspan="1" colspan="1">2.1429 (16)</td></tr><tr><td rowspan="1" colspan="1">C17—H17</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">N5—Co1</td><td rowspan="1" colspan="1">2.1739 (15)</td></tr><tr><td rowspan="1" colspan="1">C18—N4</td><td rowspan="1" colspan="1">1.300 (3)</td><td rowspan="1" colspan="1">Cl1—Co1</td><td rowspan="1" colspan="1">2.3855 (5)</td></tr><tr><td rowspan="1" colspan="1">C18—S2</td><td rowspan="1" colspan="1">1.703 (2)</td><td rowspan="1" colspan="1">Cl2A—Cl2B</td><td rowspan="1" colspan="1">0.57 (5)</td></tr><tr><td rowspan="1" colspan="1">C18—H18</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">Cl2A—Co1</td><td rowspan="1" colspan="1">2.4181 (19)</td></tr><tr><td rowspan="1" colspan="1">C19—C20</td><td rowspan="1" colspan="1">1.352 (3)</td><td rowspan="1" colspan="1">Cl2B—Co1</td><td rowspan="1" colspan="1">2.261 (9)</td></tr><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1—C1—S1</td><td rowspan="1" colspan="1">114.29 (16)</td><td rowspan="1" colspan="1">C26—C25—H25</td><td rowspan="1" colspan="1">119.0</td></tr><tr><td rowspan="1" colspan="1">N1—C1—H1</td><td rowspan="1" colspan="1">122.9</td><td rowspan="1" colspan="1">C24—C25—H25</td><td rowspan="1" colspan="1">119.0</td></tr><tr><td rowspan="1" colspan="1">S1—C1—H1</td><td rowspan="1" colspan="1">122.9</td><td rowspan="1" colspan="1">C25—C26—C27</td><td rowspan="1" colspan="1">116.32 (19)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—S1</td><td rowspan="1" colspan="1">110.12 (16)</td><td rowspan="1" colspan="1">C25—C26—H26</td><td rowspan="1" colspan="1">121.8</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H2</td><td rowspan="1" colspan="1">124.9</td><td rowspan="1" colspan="1">C27—C26—H26</td><td rowspan="1" colspan="1">121.8</td></tr><tr><td rowspan="1" colspan="1">S1—C2—H2</td><td rowspan="1" colspan="1">124.9</td><td rowspan="1" colspan="1">N6—C27—C26</td><td rowspan="1" colspan="1">131.34 (18)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—N1</td><td rowspan="1" colspan="1">114.08 (17)</td><td rowspan="1" colspan="1">N6—C27—C22</td><td rowspan="1" colspan="1">106.17 (16)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">132.60 (18)</td><td rowspan="1" colspan="1">C26—C27—C22</td><td rowspan="1" colspan="1">122.42 (18)</td></tr><tr><td rowspan="1" colspan="1">N1—C3—C4</td><td rowspan="1" colspan="1">113.32 (16)</td><td rowspan="1" colspan="1">N6—C28—C29</td><td rowspan="1" colspan="1">114.23 (16)</td></tr><tr><td rowspan="1" colspan="1">N2—C4—N3</td><td rowspan="1" colspan="1">113.06 (16)</td><td rowspan="1" colspan="1">N6—C28—H28A</td><td rowspan="1" colspan="1">108.7</td></tr><tr><td rowspan="1" colspan="1">N2—C4—C3</td><td rowspan="1" colspan="1">119.16 (16)</td><td rowspan="1" colspan="1">C29—C28—H28A</td><td rowspan="1" colspan="1">108.7</td></tr><tr><td rowspan="1" colspan="1">N3—C4—C3</td><td rowspan="1" colspan="1">127.76 (17)</td><td rowspan="1" colspan="1">N6—C28—H28B</td><td rowspan="1" colspan="1">108.7</td></tr><tr><td rowspan="1" colspan="1">N2—C5—C6</td><td rowspan="1" colspan="1">130.57 (18)</td><td rowspan="1" colspan="1">C29—C28—H28B</td><td rowspan="1" colspan="1">108.7</td></tr><tr><td rowspan="1" colspan="1">N2—C5—C10</td><td rowspan="1" colspan="1">109.28 (17)</td><td rowspan="1" colspan="1">H28A—C28—H28B</td><td rowspan="1" colspan="1">107.6</td></tr><tr><td rowspan="1" colspan="1">C6—C5—C10</td><td rowspan="1" colspan="1">120.10 (17)</td><td rowspan="1" colspan="1">C34—C29—C30</td><td rowspan="1" colspan="1">119.26 (19)</td></tr><tr><td rowspan="1" colspan="1">C7—C6—C5</td><td rowspan="1" colspan="1">117.1 (2)</td><td rowspan="1" colspan="1">C34—C29—C28</td><td rowspan="1" colspan="1">123.75 (18)</td></tr><tr><td rowspan="1" colspan="1">C7—C6—H6</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">C30—C29—C28</td><td rowspan="1" colspan="1">116.99 (18)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—H6</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">C31—C30—C29</td><td rowspan="1" colspan="1">120.2 (2)</td></tr><tr><td rowspan="1" colspan="1">C6—C7—C8</td><td rowspan="1" colspan="1">121.7 (2)</td><td rowspan="1" colspan="1">C31—C30—H30</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C6—C7—H7</td><td rowspan="1" colspan="1">119.1</td><td rowspan="1" colspan="1">C29—C30—H30</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C8—C7—H7</td><td rowspan="1" colspan="1">119.1</td><td rowspan="1" colspan="1">C32—C31—C30</td><td rowspan="1" colspan="1">120.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—C7</td><td rowspan="1" colspan="1">121.93 (19)</td><td rowspan="1" colspan="1">C32—C31—H31</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C9—C8—H8</td><td rowspan="1" colspan="1">119.0</td><td rowspan="1" colspan="1">C30—C31—H31</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C7—C8—H8</td><td rowspan="1" colspan="1">119.0</td><td rowspan="1" colspan="1">C33—C32—C31</td><td rowspan="1" colspan="1">119.8 (2)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—C10</td><td rowspan="1" colspan="1">116.2 (2)</td><td rowspan="1" colspan="1">C33—C32—H32</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">C8—C9—H9</td><td rowspan="1" colspan="1">121.9</td><td rowspan="1" colspan="1">C31—C32—H32</td><td rowspan="1" colspan="1">120.1</td></tr><tr><td rowspan="1" colspan="1">C10—C9—H9</td><td rowspan="1" colspan="1">121.9</td><td rowspan="1" colspan="1">C32—C33—C34</td><td rowspan="1" colspan="1">120.2 (2)</td></tr><tr><td rowspan="1" colspan="1">N3—C10—C9</td><td rowspan="1" colspan="1">131.1 (2)</td><td rowspan="1" colspan="1">C32—C33—H33</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">N3—C10—C5</td><td rowspan="1" colspan="1">105.95 (16)</td><td rowspan="1" colspan="1">C34—C33—H33</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C9—C10—C5</td><td rowspan="1" colspan="1">122.9 (2)</td><td rowspan="1" colspan="1">C29—C34—C33</td><td rowspan="1" colspan="1">120.3 (2)</td></tr><tr><td rowspan="1" colspan="1">N3—C11—C12</td><td rowspan="1" colspan="1">114.20 (15)</td><td rowspan="1" colspan="1">C29—C34—H34</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">N3—C11—H11A</td><td rowspan="1" colspan="1">108.7</td><td rowspan="1" colspan="1">C33—C34—H34</td><td rowspan="1" colspan="1">119.9</td></tr><tr><td rowspan="1" colspan="1">C12—C11—H11A</td><td rowspan="1" colspan="1">108.7</td><td rowspan="1" colspan="1">C1—N1—C3</td><td rowspan="1" colspan="1">111.49 (16)</td></tr><tr><td rowspan="1" colspan="1">N3—C11—H11B</td><td rowspan="1" colspan="1">108.7</td><td rowspan="1" colspan="1">C1—N1—Co1</td><td rowspan="1" colspan="1">131.34 (14)</td></tr><tr><td rowspan="1" colspan="1">C12—C11—H11B</td><td rowspan="1" colspan="1">108.7</td><td rowspan="1" colspan="1">C3—N1—Co1</td><td rowspan="1" colspan="1">116.57 (12)</td></tr><tr><td rowspan="1" colspan="1">H11A—C11—H11B</td><td rowspan="1" colspan="1">107.6</td><td rowspan="1" colspan="1">C4—N2—C5</td><td rowspan="1" colspan="1">105.28 (15)</td></tr><tr><td rowspan="1" colspan="1">C17—C12—C13</td><td rowspan="1" colspan="1">119.35 (18)</td><td rowspan="1" colspan="1">C4—N2—Co1</td><td rowspan="1" colspan="1">113.82 (12)</td></tr><tr><td rowspan="1" colspan="1">C17—C12—C11</td><td rowspan="1" colspan="1">123.18 (17)</td><td rowspan="1" colspan="1">C5—N2—Co1</td><td rowspan="1" colspan="1">139.41 (13)</td></tr><tr><td rowspan="1" colspan="1">C13—C12—C11</td><td rowspan="1" colspan="1">117.45 (17)</td><td rowspan="1" colspan="1">C4—N3—C10</td><td rowspan="1" colspan="1">106.42 (16)</td></tr><tr><td rowspan="1" colspan="1">C14—C13—C12</td><td rowspan="1" colspan="1">120.21 (19)</td><td rowspan="1" colspan="1">C4—N3—C11</td><td rowspan="1" colspan="1">128.90 (17)</td></tr><tr><td rowspan="1" colspan="1">C14—C13—H13</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">C10—N3—C11</td><td rowspan="1" colspan="1">124.67 (16)</td></tr><tr><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">C18—N4—C20</td><td rowspan="1" colspan="1">111.57 (17)</td></tr><tr><td rowspan="1" colspan="1">C15—C14—C13</td><td rowspan="1" colspan="1">119.97 (19)</td><td rowspan="1" colspan="1">C18—N4—Co1</td><td rowspan="1" colspan="1">131.45 (15)</td></tr><tr><td rowspan="1" colspan="1">C15—C14—H14</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">C20—N4—Co1</td><td rowspan="1" colspan="1">116.63 (12)</td></tr><tr><td rowspan="1" colspan="1">C13—C14—H14</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">C21—N5—C22</td><td rowspan="1" colspan="1">105.84 (15)</td></tr><tr><td rowspan="1" colspan="1">C16—C15—C14</td><td rowspan="1" colspan="1">120.30 (19)</td><td rowspan="1" colspan="1">C21—N5—Co1</td><td rowspan="1" colspan="1">115.38 (12)</td></tr><tr><td rowspan="1" colspan="1">C16—C15—H15</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">C22—N5—Co1</td><td rowspan="1" colspan="1">138.75 (12)</td></tr><tr><td rowspan="1" colspan="1">C14—C15—H15</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">C21—N6—C27</td><td rowspan="1" colspan="1">106.33 (15)</td></tr><tr><td rowspan="1" colspan="1">C15—C16—C17</td><td rowspan="1" colspan="1">120.08 (19)</td><td rowspan="1" colspan="1">C21—N6—C28</td><td rowspan="1" colspan="1">128.80 (17)</td></tr><tr><td rowspan="1" colspan="1">C15—C16—H16</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">C27—N6—C28</td><td rowspan="1" colspan="1">124.88 (16)</td></tr><tr><td rowspan="1" colspan="1">C17—C16—H16</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">C1—S1—C2</td><td rowspan="1" colspan="1">89.98 (10)</td></tr><tr><td rowspan="1" colspan="1">C12—C17—C16</td><td rowspan="1" colspan="1">120.09 (18)</td><td rowspan="1" colspan="1">C18—S2—C19</td><td rowspan="1" colspan="1">90.14 (10)</td></tr><tr><td rowspan="1" colspan="1">C12—C17—H17</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">Cl2B—Cl2A—Co1</td><td rowspan="1" colspan="1">67.3 (11)</td></tr><tr><td rowspan="1" colspan="1">C16—C17—H17</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">Cl2A—Cl2B—Co1</td><td rowspan="1" colspan="1">99 (2)</td></tr><tr><td rowspan="1" colspan="1">N4—C18—S2</td><td rowspan="1" colspan="1">114.02 (17)</td><td rowspan="1" colspan="1">N1—Co1—N4</td><td rowspan="1" colspan="1">169.37 (6)</td></tr><tr><td rowspan="1" colspan="1">N4—C18—H18</td><td rowspan="1" colspan="1">123.0</td><td rowspan="1" colspan="1">N1—Co1—N5</td><td rowspan="1" colspan="1">98.02 (6)</td></tr><tr><td rowspan="1" colspan="1">S2—C18—H18</td><td rowspan="1" colspan="1">123.0</td><td rowspan="1" colspan="1">N4—Co1—N5</td><td rowspan="1" colspan="1">75.45 (6)</td></tr><tr><td rowspan="1" colspan="1">C20—C19—S2</td><td rowspan="1" colspan="1">109.95 (17)</td><td rowspan="1" colspan="1">N1—Co1—N2</td><td rowspan="1" colspan="1">75.58 (6)</td></tr><tr><td rowspan="1" colspan="1">C20—C19—H19</td><td rowspan="1" colspan="1">125.0</td><td rowspan="1" colspan="1">N4—Co1—N2</td><td rowspan="1" colspan="1">94.82 (6)</td></tr><tr><td rowspan="1" colspan="1">S2—C19—H19</td><td rowspan="1" colspan="1">125.0</td><td rowspan="1" colspan="1">N5—Co1—N2</td><td rowspan="1" colspan="1">79.86 (5)</td></tr><tr><td rowspan="1" colspan="1">C19—C20—N4</td><td rowspan="1" colspan="1">114.31 (18)</td><td rowspan="1" colspan="1">N1—Co1—Cl2B</td><td rowspan="1" colspan="1">104.7 (9)</td></tr><tr><td rowspan="1" colspan="1">C19—C20—C21</td><td rowspan="1" colspan="1">132.2 (2)</td><td rowspan="1" colspan="1">N4—Co1—Cl2B</td><td rowspan="1" colspan="1">81.7 (8)</td></tr><tr><td rowspan="1" colspan="1">N4—C20—C21</td><td rowspan="1" colspan="1">113.53 (16)</td><td rowspan="1" colspan="1">N5—Co1—Cl2B</td><td rowspan="1" colspan="1">157.1 (8)</td></tr><tr><td rowspan="1" colspan="1">N5—C21—N6</td><td rowspan="1" colspan="1">112.85 (16)</td><td rowspan="1" colspan="1">N2—Co1—Cl2B</td><td rowspan="1" colspan="1">102.9 (11)</td></tr><tr><td rowspan="1" colspan="1">N5—C21—C20</td><td rowspan="1" colspan="1">118.58 (17)</td><td rowspan="1" colspan="1">N1—Co1—Cl1</td><td rowspan="1" colspan="1">91.26 (4)</td></tr><tr><td rowspan="1" colspan="1">N6—C21—C20</td><td rowspan="1" colspan="1">128.53 (17)</td><td rowspan="1" colspan="1">N4—Co1—Cl1</td><td rowspan="1" colspan="1">96.61 (4)</td></tr><tr><td rowspan="1" colspan="1">N5—C22—C23</td><td rowspan="1" colspan="1">130.57 (17)</td><td rowspan="1" colspan="1">N5—Co1—Cl1</td><td rowspan="1" colspan="1">86.27 (4)</td></tr><tr><td rowspan="1" colspan="1">N5—C22—C27</td><td rowspan="1" colspan="1">108.81 (16)</td><td rowspan="1" colspan="1">N2—Co1—Cl1</td><td rowspan="1" colspan="1">159.21 (4)</td></tr><tr><td rowspan="1" colspan="1">C23—C22—C27</td><td rowspan="1" colspan="1">120.57 (17)</td><td rowspan="1" colspan="1">Cl2B—Co1—Cl1</td><td rowspan="1" colspan="1">95.9 (9)</td></tr><tr><td rowspan="1" colspan="1">C24—C23—C22</td><td rowspan="1" colspan="1">117.13 (18)</td><td rowspan="1" colspan="1">N1—Co1—Cl2A</td><td rowspan="1" colspan="1">93.31 (8)</td></tr><tr><td rowspan="1" colspan="1">C24—C23—H23</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">N4—Co1—Cl2A</td><td rowspan="1" colspan="1">91.82 (8)</td></tr><tr><td rowspan="1" colspan="1">C22—C23—H23</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">N5—Co1—Cl2A</td><td rowspan="1" colspan="1">164.99 (7)</td></tr><tr><td rowspan="1" colspan="1">C23—C24—C25</td><td rowspan="1" colspan="1">121.7 (2)</td><td rowspan="1" colspan="1">N2—Co1—Cl2A</td><td rowspan="1" colspan="1">93.56 (5)</td></tr><tr><td rowspan="1" colspan="1">C23—C24—H24</td><td rowspan="1" colspan="1">119.2</td><td rowspan="1" colspan="1">Cl2B—Co1—Cl2A</td><td rowspan="1" colspan="1">13.4 (12)</td></tr><tr><td rowspan="1" colspan="1">C25—C24—H24</td><td rowspan="1" colspan="1">119.2</td><td rowspan="1" colspan="1">Cl1—Co1—Cl2A</td><td rowspan="1" colspan="1">103.35 (3)</td></tr><tr><td rowspan="1" colspan="1">C26—C25—C24</td><td rowspan="1" colspan="1">121.90 (19)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e3699"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="5"><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1"><italic>D</italic>—H···<italic>A</italic></td><td rowspan="1" colspan="1"><italic>D</italic>—H</td><td rowspan="1" colspan="1">H···<italic>A</italic></td><td rowspan="1" colspan="1"><italic>D</italic>···<italic>A</italic></td><td rowspan="1" colspan="1"><italic>D</italic>—H···<italic>A</italic></td></tr><tr><td rowspan="1" colspan="1">C11—H11<italic>A</italic>···Cl2<italic>A</italic><sup>i</sup></td><td rowspan="1" colspan="1">0.99</td><td rowspan="1" colspan="1">2.77</td><td rowspan="1" colspan="1">3.693 (2)</td><td rowspan="1" colspan="1">155</td></tr><tr><td rowspan="1" colspan="1">C14—H14···Cl1<sup>ii</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.69</td><td rowspan="1" colspan="1">3.584 (2)</td><td rowspan="1" colspan="1">157</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+1, −<italic>y</italic>, −<italic>z</italic>+1; (ii) <italic>x</italic>+1, <italic>y</italic>−1, <italic>z</italic>.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Bruker (2009). <italic>APEX2</italic>, <italic>SAINT</italic> and <italic>SADABS</italic> Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Devereux, M. O., Shea, D., Kellett, A., McCann, M., Walsh, M., Egan, D., Deegan, C., Kędziora, K., Rosair, G. & Müller-Bunz, H. (2007). <italic>J. Inorg. Biochem.</italic><bold>101</bold>, 881–892.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Farrugia, L. J. (2012). <italic>J. Appl. Cryst.</italic><bold>45</bold>, 849–854.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Kowala, C., Murray, K. S., Swan, J. M. & West, B. O. (1971). <italic>Aust. J. Chem.</italic><bold>24</bold>, 1369–1375.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Spek, A. L. (2009). <italic>Acta Cryst.</italic> D<bold>65</bold>, 148–155.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Westrip, S. P. (2010). <italic>J. Appl. Cryst.</italic><bold>43</bold>, 920–925.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Yan-Jua, C. U. & Guang-Ganga, L. I. (2009). <italic>Chin. J. Struct. Chem.</italic><bold>28</bold>, 434–438.</mixed-citation></ref></ref-list></back><floats-group><table-wrap id="table1" position="float"><label>Table 1</label><caption><title>Hydrogen-bond geometry (Å, °)</title></caption><table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H</th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th></tr></thead><tbody valign="top"><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C11—H11<italic>A</italic>⋯Cl2<italic>A</italic><sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.99</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.77</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.693 (2)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">155</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C14—H14⋯Cl1<sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.95</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.69</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.584 (2)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">157</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-69-000m5-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-69-000m5-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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