Crystal structure of bis(azido-κN)bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ2N2,N3]cobalt(II)
Identifieur interne : 000049 ( Pmc/Corpus ); précédent : 000048; suivant : 000050Crystal structure of bis(azido-κN)bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ2N2,N3]cobalt(II)
Auteurs : Abdelhakim Laachir ; Fouad Bentiss ; Salaheddine Guesmi ; Mohamed Saadi ; Lahcen El AmmariSource :
- Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2015.
Abstract
The structure of the title compound is isotypic with that of the analogous nickel(II) complex, in which the CoN6 core shows an axially weakly compressed octahedral geometry as opposed to the almost regular geometry exhibited by the NiN6 octahedron.
Url:
DOI: 10.1107/S2056989015006544
PubMed: 25995853
PubMed Central: 4420119
Links to Exploration step
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Crystal structure of bis(azido-κ<italic>N</italic>)bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ<sup>2</sup><italic>N</italic><sup>2</sup>,<italic>N</italic><sup>3</sup>]cobalt(II)</title><author><name sortKey="Laachir, Abdelhakim" sort="Laachir, Abdelhakim" uniqKey="Laachir A" first="Abdelhakim" last="Laachir">Abdelhakim Laachir</name><affiliation><nlm:aff id="a">Laboratoire de Chimie de Coordination et d’Analytique (LCCA), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Bentiss, Fouad" sort="Bentiss, Fouad" uniqKey="Bentiss F" first="Fouad" last="Bentiss">Fouad Bentiss</name><affiliation><nlm:aff id="b">Laboratoire de Catalyse et de Corrosion de Matériaux (LCCM), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Guesmi, Salaheddine" sort="Guesmi, Salaheddine" uniqKey="Guesmi S" first="Salaheddine" last="Guesmi">Salaheddine Guesmi</name><affiliation><nlm:aff id="a">Laboratoire de Chimie de Coordination et d’Analytique (LCCA), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Saadi, Mohamed" sort="Saadi, Mohamed" uniqKey="Saadi M" first="Mohamed" last="Saadi">Mohamed Saadi</name><affiliation><nlm:aff id="c">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</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="c">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">25995853</idno><idno type="pmc">4420119</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4420119</idno><idno type="RBID">PMC:4420119</idno><idno type="doi">10.1107/S2056989015006544</idno><date when="2015">2015</date><idno type="wicri:Area/Pmc/Corpus">000049</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000049</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Crystal structure of bis(azido-κ<italic>N</italic>)bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ<sup>2</sup><italic>N</italic><sup>2</sup>,<italic>N</italic><sup>3</sup>]cobalt(II)</title><author><name sortKey="Laachir, Abdelhakim" sort="Laachir, Abdelhakim" uniqKey="Laachir A" first="Abdelhakim" last="Laachir">Abdelhakim Laachir</name><affiliation><nlm:aff id="a">Laboratoire de Chimie de Coordination et d’Analytique (LCCA), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Bentiss, Fouad" sort="Bentiss, Fouad" uniqKey="Bentiss F" first="Fouad" last="Bentiss">Fouad Bentiss</name><affiliation><nlm:aff id="b">Laboratoire de Catalyse et de Corrosion de Matériaux (LCCM), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Guesmi, Salaheddine" sort="Guesmi, Salaheddine" uniqKey="Guesmi S" first="Salaheddine" last="Guesmi">Salaheddine Guesmi</name><affiliation><nlm:aff id="a">Laboratoire de Chimie de Coordination et d’Analytique (LCCA), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Saadi, Mohamed" sort="Saadi, Mohamed" uniqKey="Saadi M" first="Mohamed" last="Saadi">Mohamed Saadi</name><affiliation><nlm:aff id="c">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</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="c">Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></nlm:aff></affiliation></author></analytic><series><title level="j">Acta Crystallographica Section E: Crystallographic Communications</title><idno type="eISSN">2056-9890</idno><imprint><date when="2015">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The structure of the title compound is isotypic with that of the analogous nickel(II) complex, in which the CoN<sub>6</sub> core shows an axially weakly compressed octahedral geometry as opposed to the almost regular geometry exhibited by the NiN<sub>6</sub> octahedron.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><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 E Crystallogr Commun</journal-id><journal-id journal-id-type="iso-abbrev">Acta Crystallogr E Crystallogr Commun</journal-id><journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id><journal-title-group><journal-title>Acta Crystallographica Section E: Crystallographic Communications</journal-title></journal-title-group><issn pub-type="epub">2056-9890</issn><publisher><publisher-name>International Union of Crystallography</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">25995853</article-id><article-id pub-id-type="pmc">4420119</article-id><article-id pub-id-type="publisher-id">rz5153</article-id><article-id pub-id-type="doi">10.1107/S2056989015006544</article-id><article-id pub-id-type="coden">ACSECI</article-id><article-id pub-id-type="pii">S2056989015006544</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject></subj-group></article-categories><title-group><article-title>Crystal structure of bis(azido-κ<italic>N</italic>)bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ<sup>2</sup><italic>N</italic><sup>2</sup>,<italic>N</italic><sup>3</sup>]cobalt(II)</article-title><alt-title><italic>[Co(N<sub>3</sub>)<sub>2</sub>(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>]</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Laachir</surname><given-names>Abdelhakim</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Bentiss</surname><given-names>Fouad</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Guesmi</surname><given-names>Salaheddine</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><contrib contrib-type="author"><name><surname>Saadi</surname><given-names>Mohamed</given-names></name><xref ref-type="aff" rid="c">c</xref></contrib><contrib contrib-type="author"><name><surname>El Ammari</surname><given-names>Lahcen</given-names></name><xref ref-type="aff" rid="c">c</xref></contrib><aff id="a"><label>a</label>Laboratoire de Chimie de Coordination et d’Analytique (LCCA), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></aff><aff id="b"><label>b</label>Laboratoire de Catalyse et de Corrosion de Matériaux (LCCM), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida,<country>Morocco</country></aff><aff id="c"><label>c</label>Laboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat,<country>Morocco</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>salaheddine_guesmi@yahoo.fr</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>5</month><year>2015</year></pub-date><pub-date pub-type="epub"><day>09</day><month>4</month><year>2015</year></pub-date><pub-date pub-type="pmc-release"><day>09</day><month>4</month><year>2015</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>71</volume><issue>Pt 5</issue><issue-id pub-id-type="publisher-id">e150500</issue-id><fpage>452</fpage><lpage>454</lpage><history><date date-type="received"><day>19</day><month>3</month><year>2015</year></date><date date-type="accepted"><day>31</day><month>3</month><year>2015</year></date></history><permissions><copyright-statement>© Laachir et al. 2015</copyright-statement><copyright-year>2015</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/S2056989015006544">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract abstract-type="toc"><p>The structure of the title compound is isotypic with that of the analogous nickel(II) complex, in which the CoN<sub>6</sub> core shows an axially weakly compressed octahedral geometry as opposed to the almost regular geometry exhibited by the NiN<sub>6</sub> octahedron.</p></abstract><abstract><p>In the mononuclear title complex, [Co(N<sub>3</sub>)<sub>2</sub>(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>], the cobalt(II) atom is located on an inversion centre and displays an axially weakly compressed octahedral coordination geometry. The equatorial positions are occupied by the N atoms of two 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole ligands, whereas the axial positions are occupied by N atoms of the azide anions. The thiadiazole and pyridine rings linked to the metal are almost coplanar, with a maximum deviation from the mean plane of 0.0273 (16) Å. The cohesion of the crystal is ensured by weak C—H⋯N hydrogen bonds and by π–π interactions between pyridine rings [intercentroid distance = 3.6356 (11) Å], forming a layered arrangement parallel to (001). The structure of the title compound is isotypic with that of the analogous nickel(II) complex [Laachir <italic>et al.</italic> (2013<xref ref-type="bibr" rid="bb8"> ▸</xref>). <italic>Acta Cryst.</italic> E<bold>69</bold>, m351–m352].</p></abstract><kwd-group><kwd>crystal structure</kwd><kwd>transition metal</kwd><kwd>2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole ligand</kwd><kwd>azide compounds</kwd><kwd>hydrogen bonding</kwd><kwd>π–π interactions</kwd></kwd-group></article-meta></front><body><sec id="sec1"><title>Chemical context </title><p>In recent years, the use of the ligand 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole has been studied for the synthesis of numerous complexes with transition-metal salts. An interesting feature of the metal–ligand chemistry of these compounds is that the resulting complexes can be mononuclear (Bentiss <italic>et al.</italic>, 2011<italic>a</italic><xref ref-type="bibr" rid="bb1"> ▸</xref>; 2012<xref ref-type="bibr" rid="bb4"> ▸</xref>; Kaase <italic>et al.</italic>, 2014<xref ref-type="bibr" rid="bb7"> ▸</xref>) or binuclear (Bentiss <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb3"> ▸</xref>; Laachir <italic>et al.</italic>, 2013<xref ref-type="bibr" rid="bb8"> ▸</xref>). Another preparation method involves the use of the organic ligand and pseudohalide ions, especially the azide ion which is known to exhibit different coordination modes (Nath & Baruah, 2012<xref ref-type="bibr" rid="bb11"> ▸</xref>; Ray <italic>et al.</italic>, 2011<xref ref-type="bibr" rid="bb12"> ▸</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-71-00452-scheme1.jpg" position="float"></graphic></chem-struct></p></sec><sec id="sec2"><title>Structural commentary </title><p>The structure of the title compound (Fig. 1<xref ref-type="fig" rid="fig1"> ▸</xref>) is isotypic with its nickel(II) analogue (Laachir <italic>et al.</italic>, 2015<xref ref-type="bibr" rid="bb9"> ▸</xref>) and similar to that of the homologous compound, [Co(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>]·2BF<sub>4</sub>, in which the water molecules are substituted by azide ions which at the same time neutralize the positive charge of Co<sup>2+</sup> (Bentiss <italic>et al.</italic>, 2011<italic>b</italic><xref ref-type="bibr" rid="bb2"> ▸</xref>). The main difference between the two structures lies in the values of the dihedral angle between the two pyridine rings: this is 18.72 (6)° in the hydrated molecule, whereas it is 3.03 (2)° in the title molecule, (I)<xref ref-type="chem" rid="scheme1"></xref>. The dihedral angles formed by the thiadiazole ring and the pyridine rings N1/C1–C4 and N2/C8–C11 in (I)<xref ref-type="chem" rid="scheme1"></xref> are 2.87 (9) and 1.1 (2)°, respectively. The cobalt cation, which is located on an inversion centre, shows an axially weakly compressed octahedral coordination geometry with the equatorial plane provided by four nitrogen atoms belonging to the pyridine and thiadiazole rings of two organic ligands [Co1—N3 = 2.1301 (14) and Co1—N4 = 2.1535 (14) Å] and the axial positions occupied by two nitrogen atoms from azide anions [Co1—N5 = 2.1132 (17) Å].</p></sec><sec id="sec3"><title>Supramolecular features </title><p>In the crystal, the molecules are linked by π–π interactions between pyridine rings [intercentroid distance = 3.6356 (11) Å] and by weak C—H⋯N hydrogen bonds (Table 1<xref ref-type="table" rid="table1"> ▸</xref>), forming a layered arrangement parallel to (001) (Fig. 2<xref ref-type="fig" rid="fig2"> ▸</xref>). The layers are connected by further C—H⋯N hydrogen bonds into a three-dimensional network.</p></sec><sec id="sec4"><title>Synthesis and crystallization </title><p>The ligand 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole (noted <italic>L</italic>) was synthesized as described previously by Lebrini <italic>et al.</italic> (2005<xref ref-type="bibr" rid="bb10"> ▸</xref>). The complex [Co<italic>L</italic><sub>2</sub>(N<sub>3</sub>)<sub>2</sub>] was synthesized in bulk quantity by dropwise addition with constant stirring at room temperature of an aqueous solution of NaN<sub>3</sub> (0.4 mmol, 26 mg) to an ethanol/water solution (1:1 <italic>v</italic>/<italic>v</italic>) of <italic>L</italic> (0.1 mmol, 24 mg) and CoCl<sub>2</sub>·6H<sub>2</sub>O (0.1 mmol, 24 mg). The red-coloured solid precipitated was filtered and washed with cold ethanol. Single crystals of the title compound suitable for X-ray data collection were obtained by slow interdiffusion of a solution of CoCl<sub>2</sub>·6H<sub>2</sub>O and <italic>L</italic> in acetonitrile into NaN<sub>3</sub> dissolved in water. Red block-shaped single crystals appeared after one month. The crystals were washed with water and dried under vacuum (yield 60%). Analysis calculated for C<sub>24</sub>H<sub>16</sub>N<sub>14</sub>CoS<sub>2</sub>: C, 46.23; H, 2.59; N, 31.45 S, 10.28. Found: C, 46.42; H, 2.63; N, 31.35; S, 10.51.</p><p><bold>CAUTION!</bold> Azide compounds are potentially explosive. Only a small amount of material should be prepared and handled with care.</p></sec><sec id="sec5"><title>Refinement </title><p>Crystal data, data collection and structure refinement details are summarized in Table 2<xref ref-type="table" rid="table2"> ▸</xref>. H atoms were located in a difference Fourier map and treated as riding, with C—H = 0.93 Å, and with <italic>U</italic><sub>iso</sub>(H) = 1.2 <italic>U</italic><sub>eq</sub>(C). Two outliers (002 and <inline-formula><inline-graphic xlink:href="e-71-00452-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>24) were omitted in the last cycles of refinement.</p></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data"><p>Crystal structure: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S2056989015006544/rz5153sup1.cif">10.1107/S2056989015006544/rz5153sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-71-00452-sup1.cif" xlink:type="simple" id="d36e173" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S2056989015006544/rz5153Isup2.hkl">10.1107/S2056989015006544/rz5153Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-71-00452-Isup2.hkl" xlink:type="simple" id="d36e180" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>CCDC reference: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1057234">1057234</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><p>Additional supporting information: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?rz5153&file=rz5153sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?rz5153sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?rz5153&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><ack><p>The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and Chouaib Doukkali University, El Jadida, Morocco, for financial support.</p></ack><app-group><app><title>supplementary crystallographic
information</title><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e36"><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">[Co(N<sub>3</sub>)<sub>2</sub>(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>]</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 634</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 623.56</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.587 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>2<sub>1</sub>/<italic>c</italic></td><td rowspan="1" colspan="1">Mo <italic>K</italic>α radiation, λ = 0.71073 Å</td></tr><tr><td rowspan="1" colspan="1">Hall symbol: -P 2ybc</td><td rowspan="1" colspan="1">Cell parameters from 3667 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 7.8004 (3) Å</td><td rowspan="1" colspan="1">θ = 2.6–29.6°</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 8.2439 (3) Å</td><td rowspan="1" colspan="1">µ = 0.86 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 20.3222 (8) Å</td><td rowspan="1" colspan="1"><italic>T</italic> = 296 K</td></tr><tr><td rowspan="1" colspan="1">β = 92.910 (2)°</td><td rowspan="1" colspan="1">Block, red</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1305.15 (9) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.39 × 0.31 × 0.18 mm</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 2</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e174"><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 APEXII CCD diffractometer</td><td rowspan="1" colspan="1">3667 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">2884 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">Graphite monochromator</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.043</td></tr><tr><td rowspan="1" colspan="1">φ and ω scans</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 29.6°, θ<sub>min</sub> = 2.6°</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> = −8→10</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.640, <italic>T</italic><sub>max</sub> = 0.747</td><td rowspan="1" colspan="1"><italic>k</italic> = −11→11</td></tr><tr><td rowspan="1" colspan="1">27415 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −28→28</td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e291"><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">Primary atom site location: structure-invariant direct methods</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1">Secondary atom site location: difference Fourier map</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.035</td><td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.088</td><td rowspan="1" colspan="1">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.03</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0381<italic>P</italic>)<sup>2</sup> + 0.5683<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">3667 reflections</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1">187 parameters</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.70 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">0 restraints</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.26 e Å<sup>−</sup><sup>3</sup></td></tr></table></table-wrap></sec><sec id="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e449"><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> >
σ(<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="d1e549"><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"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.7907 (3)</td><td rowspan="1" colspan="1">0.4986 (3)</td><td rowspan="1" colspan="1">0.07266 (12)</td><td rowspan="1" colspan="1">0.0486 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">0.8731</td><td rowspan="1" colspan="1">0.5035</td><td rowspan="1" colspan="1">0.0412</td><td rowspan="1" colspan="1">0.058*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.8166 (3)</td><td rowspan="1" colspan="1">0.5770 (3)</td><td rowspan="1" colspan="1">0.13200 (13)</td><td rowspan="1" colspan="1">0.0540 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">0.9169</td><td rowspan="1" colspan="1">0.6353</td><td rowspan="1" colspan="1">0.1416</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.6910 (3)</td><td rowspan="1" colspan="1">0.5672 (3)</td><td rowspan="1" colspan="1">0.17662 (13)</td><td rowspan="1" colspan="1">0.0568 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.7097</td><td rowspan="1" colspan="1">0.6203</td><td rowspan="1" colspan="1">0.2167</td><td rowspan="1" colspan="1">0.068*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.5445 (2)</td><td rowspan="1" colspan="1">0.4873 (2)</td><td rowspan="1" colspan="1">0.16646 (9)</td><td rowspan="1" colspan="1">0.0448 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.5212 (2)</td><td rowspan="1" colspan="1">0.4114 (2)</td><td rowspan="1" colspan="1">0.10851 (9)</td><td rowspan="1" colspan="1">0.0316 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.3585 (2)</td><td rowspan="1" colspan="1">0.3225 (2)</td><td rowspan="1" colspan="1">0.10077 (8)</td><td rowspan="1" colspan="1">0.0298 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0891 (2)</td><td rowspan="1" colspan="1">0.1991 (2)</td><td rowspan="1" colspan="1">0.11550 (8)</td><td rowspan="1" colspan="1">0.0285 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">−0.0761 (2)</td><td rowspan="1" colspan="1">0.1314 (2)</td><td rowspan="1" colspan="1">0.13257 (8)</td><td rowspan="1" colspan="1">0.0276 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">−0.1510 (2)</td><td rowspan="1" colspan="1">0.1627 (2)</td><td rowspan="1" colspan="1">0.19143 (8)</td><td rowspan="1" colspan="1">0.0338 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9</td><td rowspan="1" colspan="1">−0.0963</td><td rowspan="1" colspan="1">0.2283</td><td rowspan="1" colspan="1">0.2233</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">−0.3087 (2)</td><td rowspan="1" colspan="1">0.0943 (2)</td><td rowspan="1" colspan="1">0.20186 (9)</td><td rowspan="1" colspan="1">0.0369 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">−0.3623</td><td rowspan="1" colspan="1">0.1133</td><td rowspan="1" colspan="1">0.2410</td><td rowspan="1" colspan="1">0.044*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">−0.3856 (2)</td><td rowspan="1" colspan="1">−0.0022 (2)</td><td rowspan="1" colspan="1">0.15379 (10)</td><td rowspan="1" colspan="1">0.0382 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">−0.4920</td><td rowspan="1" colspan="1">−0.0493</td><td rowspan="1" colspan="1">0.1599</td><td rowspan="1" colspan="1">0.046*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">−0.3022 (2)</td><td rowspan="1" colspan="1">−0.0285 (2)</td><td rowspan="1" colspan="1">0.09601 (9)</td><td rowspan="1" colspan="1">0.0348 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">−0.3547</td><td rowspan="1" colspan="1">−0.0941</td><td rowspan="1" colspan="1">0.0637</td><td rowspan="1" colspan="1">0.042*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.6406 (2)</td><td rowspan="1" colspan="1">0.4123 (2)</td><td rowspan="1" colspan="1">0.06039 (10)</td><td rowspan="1" colspan="1">0.0383 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.6204</td><td rowspan="1" colspan="1">0.3565</td><td rowspan="1" colspan="1">0.0210</td><td rowspan="1" colspan="1">0.046*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.30958 (18)</td><td rowspan="1" colspan="1">0.23430 (19)</td><td rowspan="1" colspan="1">0.05046 (7)</td><td rowspan="1" colspan="1">0.0314 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.15296 (18)</td><td rowspan="1" colspan="1">0.16405 (19)</td><td rowspan="1" colspan="1">0.05884 (7)</td><td rowspan="1" colspan="1">0.0307 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">−0.14945 (18)</td><td rowspan="1" colspan="1">0.03680 (18)</td><td rowspan="1" colspan="1">0.08497 (7)</td><td rowspan="1" colspan="1">0.0285 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.1294 (2)</td><td rowspan="1" colspan="1">−0.1959 (2)</td><td rowspan="1" colspan="1">0.04761 (8)</td><td rowspan="1" colspan="1">0.0425 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N6</td><td rowspan="1" colspan="1">0.1687 (2)</td><td rowspan="1" colspan="1">−0.1872 (2)</td><td rowspan="1" colspan="1">0.10472 (8)</td><td rowspan="1" colspan="1">0.0394 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N7</td><td rowspan="1" colspan="1">0.2046 (3)</td><td rowspan="1" colspan="1">−0.1805 (3)</td><td rowspan="1" colspan="1">0.16093 (9)</td><td rowspan="1" colspan="1">0.0650 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.21579 (6)</td><td rowspan="1" colspan="1">0.32700 (6)</td><td rowspan="1" colspan="1">0.16328 (2)</td><td rowspan="1" colspan="1">0.03604 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Co1</td><td rowspan="1" colspan="1">0.0000</td><td rowspan="1" colspan="1">0.0000</td><td rowspan="1" colspan="1">0.0000</td><td rowspan="1" colspan="1">0.02677 (10)</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="d1e969"><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">0.0316 (10)</td><td rowspan="1" colspan="1">0.0552 (13)</td><td rowspan="1" colspan="1">0.0600 (14)</td><td rowspan="1" colspan="1">−0.0009 (10)</td><td rowspan="1" colspan="1">0.0134 (9)</td><td rowspan="1" colspan="1">0.0183 (11)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0366 (11)</td><td rowspan="1" colspan="1">0.0422 (12)</td><td rowspan="1" colspan="1">0.0829 (17)</td><td rowspan="1" colspan="1">−0.0157 (10)</td><td rowspan="1" colspan="1">0.0016 (11)</td><td rowspan="1" colspan="1">0.0003 (12)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0475 (13)</td><td rowspan="1" colspan="1">0.0543 (14)</td><td rowspan="1" colspan="1">0.0687 (15)</td><td rowspan="1" colspan="1">−0.0162 (11)</td><td rowspan="1" colspan="1">0.0041 (11)</td><td rowspan="1" colspan="1">−0.0261 (12)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0358 (9)</td><td rowspan="1" colspan="1">0.0484 (10)</td><td rowspan="1" colspan="1">0.0508 (10)</td><td rowspan="1" colspan="1">−0.0103 (8)</td><td rowspan="1" colspan="1">0.0086 (8)</td><td rowspan="1" colspan="1">−0.0184 (8)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0270 (8)</td><td rowspan="1" colspan="1">0.0304 (9)</td><td rowspan="1" colspan="1">0.0371 (9)</td><td rowspan="1" colspan="1">−0.0022 (7)</td><td rowspan="1" colspan="1">0.0009 (7)</td><td rowspan="1" colspan="1">0.0008 (7)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0269 (8)</td><td rowspan="1" colspan="1">0.0349 (9)</td><td rowspan="1" colspan="1">0.0278 (8)</td><td rowspan="1" colspan="1">−0.0020 (7)</td><td rowspan="1" colspan="1">0.0028 (7)</td><td rowspan="1" colspan="1">0.0002 (7)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0292 (8)</td><td rowspan="1" colspan="1">0.0349 (9)</td><td rowspan="1" colspan="1">0.0213 (7)</td><td rowspan="1" colspan="1">−0.0025 (7)</td><td rowspan="1" colspan="1">0.0004 (6)</td><td rowspan="1" colspan="1">−0.0024 (6)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0277 (8)</td><td rowspan="1" colspan="1">0.0330 (9)</td><td rowspan="1" colspan="1">0.0223 (7)</td><td rowspan="1" colspan="1">−0.0009 (7)</td><td rowspan="1" colspan="1">0.0028 (6)</td><td rowspan="1" colspan="1">0.0013 (6)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0368 (9)</td><td rowspan="1" colspan="1">0.0432 (10)</td><td rowspan="1" colspan="1">0.0216 (8)</td><td rowspan="1" colspan="1">−0.0008 (8)</td><td rowspan="1" colspan="1">0.0040 (7)</td><td rowspan="1" colspan="1">−0.0026 (7)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0371 (9)</td><td rowspan="1" colspan="1">0.0468 (11)</td><td rowspan="1" colspan="1">0.0280 (9)</td><td rowspan="1" colspan="1">0.0032 (9)</td><td rowspan="1" colspan="1">0.0118 (7)</td><td rowspan="1" colspan="1">0.0033 (8)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0308 (9)</td><td rowspan="1" colspan="1">0.0445 (11)</td><td rowspan="1" colspan="1">0.0403 (10)</td><td rowspan="1" colspan="1">−0.0032 (8)</td><td rowspan="1" colspan="1">0.0112 (8)</td><td rowspan="1" colspan="1">0.0055 (8)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0310 (9)</td><td rowspan="1" colspan="1">0.0393 (10)</td><td rowspan="1" colspan="1">0.0342 (9)</td><td rowspan="1" colspan="1">−0.0060 (8)</td><td rowspan="1" colspan="1">0.0042 (7)</td><td rowspan="1" colspan="1">−0.0026 (7)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0353 (9)</td><td rowspan="1" colspan="1">0.0443 (11)</td><td rowspan="1" colspan="1">0.0355 (10)</td><td rowspan="1" colspan="1">0.0012 (8)</td><td rowspan="1" colspan="1">0.0029 (8)</td><td rowspan="1" colspan="1">0.0038 (8)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0284 (7)</td><td rowspan="1" colspan="1">0.0407 (8)</td><td rowspan="1" colspan="1">0.0252 (7)</td><td rowspan="1" colspan="1">−0.0078 (6)</td><td rowspan="1" colspan="1">0.0032 (6)</td><td rowspan="1" colspan="1">−0.0028 (6)</td></tr><tr><td rowspan="1" colspan="1">N3</td><td rowspan="1" colspan="1">0.0281 (7)</td><td rowspan="1" colspan="1">0.0411 (8)</td><td rowspan="1" colspan="1">0.0229 (7)</td><td rowspan="1" colspan="1">−0.0064 (6)</td><td rowspan="1" colspan="1">0.0028 (6)</td><td rowspan="1" colspan="1">−0.0027 (6)</td></tr><tr><td rowspan="1" colspan="1">N4</td><td rowspan="1" colspan="1">0.0283 (7)</td><td rowspan="1" colspan="1">0.0340 (7)</td><td rowspan="1" colspan="1">0.0235 (7)</td><td rowspan="1" colspan="1">−0.0032 (6)</td><td rowspan="1" colspan="1">0.0034 (6)</td><td rowspan="1" colspan="1">−0.0012 (6)</td></tr><tr><td rowspan="1" colspan="1">N5</td><td rowspan="1" colspan="1">0.0489 (10)</td><td rowspan="1" colspan="1">0.0472 (10)</td><td rowspan="1" colspan="1">0.0316 (8)</td><td rowspan="1" colspan="1">0.0043 (8)</td><td rowspan="1" colspan="1">0.0037 (7)</td><td rowspan="1" colspan="1">0.0004 (7)</td></tr><tr><td rowspan="1" colspan="1">N6</td><td rowspan="1" colspan="1">0.0301 (8)</td><td rowspan="1" colspan="1">0.0476 (10)</td><td rowspan="1" colspan="1">0.0404 (9)</td><td rowspan="1" colspan="1">−0.0064 (7)</td><td rowspan="1" colspan="1">0.0010 (7)</td><td rowspan="1" colspan="1">0.0125 (7)</td></tr><tr><td rowspan="1" colspan="1">N7</td><td rowspan="1" colspan="1">0.0610 (13)</td><td rowspan="1" colspan="1">0.0935 (17)</td><td rowspan="1" colspan="1">0.0391 (10)</td><td rowspan="1" colspan="1">−0.0169 (12)</td><td rowspan="1" colspan="1">−0.0125 (9)</td><td rowspan="1" colspan="1">0.0198 (10)</td></tr><tr><td rowspan="1" colspan="1">S1</td><td rowspan="1" colspan="1">0.0322 (2)</td><td rowspan="1" colspan="1">0.0481 (3)</td><td rowspan="1" colspan="1">0.0282 (2)</td><td rowspan="1" colspan="1">−0.0092 (2)</td><td rowspan="1" colspan="1">0.00487 (17)</td><td rowspan="1" colspan="1">−0.01202 (19)</td></tr><tr><td rowspan="1" colspan="1">Co1</td><td rowspan="1" colspan="1">0.02599 (16)</td><td rowspan="1" colspan="1">0.03633 (19)</td><td rowspan="1" colspan="1">0.01818 (15)</td><td rowspan="1" colspan="1">−0.00561 (14)</td><td rowspan="1" colspan="1">0.00290 (11)</td><td rowspan="1" colspan="1">−0.00329 (13)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e1387"><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—C2</td><td rowspan="1" colspan="1">1.374 (3)</td><td rowspan="1" colspan="1">C9—H9</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C1—C4</td><td rowspan="1" colspan="1">1.382 (3)</td><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.374 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—H1</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.371 (3)</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.388 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—H2</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C3—N1</td><td rowspan="1" colspan="1">1.326 (3)</td><td rowspan="1" colspan="1">C12—N4</td><td rowspan="1" colspan="1">1.337 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N1—C5</td><td rowspan="1" colspan="1">1.338 (2)</td><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">C5—C4</td><td rowspan="1" colspan="1">1.384 (3)</td><td rowspan="1" colspan="1">N2—N3</td><td rowspan="1" colspan="1">1.3704 (19)</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.467 (2)</td><td rowspan="1" colspan="1">N3—Co1</td><td rowspan="1" colspan="1">2.1301 (14)</td></tr><tr><td rowspan="1" colspan="1">C6—N2</td><td rowspan="1" colspan="1">1.297 (2)</td><td rowspan="1" colspan="1">N4—Co1</td><td rowspan="1" colspan="1">2.1535 (14)</td></tr><tr><td rowspan="1" colspan="1">C6—S1</td><td rowspan="1" colspan="1">1.7317 (16)</td><td rowspan="1" colspan="1">N5—N6</td><td rowspan="1" colspan="1">1.187 (2)</td></tr><tr><td rowspan="1" colspan="1">C7—N3</td><td rowspan="1" colspan="1">1.310 (2)</td><td rowspan="1" colspan="1">N5—Co1</td><td rowspan="1" colspan="1">2.1132 (17)</td></tr><tr><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.462 (2)</td><td rowspan="1" colspan="1">N6—N7</td><td rowspan="1" colspan="1">1.164 (2)</td></tr><tr><td rowspan="1" colspan="1">C7—S1</td><td rowspan="1" colspan="1">1.7128 (17)</td><td rowspan="1" colspan="1">Co1—N5<sup>i</sup></td><td rowspan="1" colspan="1">2.1132 (17)</td></tr><tr><td rowspan="1" colspan="1">C8—N4</td><td rowspan="1" colspan="1">1.347 (2)</td><td rowspan="1" colspan="1">Co1—N3<sup>i</sup></td><td rowspan="1" colspan="1">2.1301 (14)</td></tr><tr><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.382 (2)</td><td rowspan="1" colspan="1">Co1—N4<sup>i</sup></td><td rowspan="1" colspan="1">2.1535 (14)</td></tr><tr><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.380 (3)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></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">C2—C1—C4</td><td rowspan="1" colspan="1">119.10 (19)</td><td rowspan="1" colspan="1">N4—C12—C11</td><td rowspan="1" colspan="1">122.64 (17)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—H1</td><td rowspan="1" colspan="1">120.5</td><td rowspan="1" colspan="1">N4—C12—H12</td><td rowspan="1" colspan="1">118.7</td></tr><tr><td rowspan="1" colspan="1">C4—C1—H1</td><td rowspan="1" colspan="1">120.5</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">118.7</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">118.31 (19)</td><td rowspan="1" colspan="1">C1—C4—C5</td><td rowspan="1" colspan="1">118.00 (19)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H2</td><td rowspan="1" colspan="1">120.8</td><td rowspan="1" colspan="1">C1—C4—H4</td><td rowspan="1" colspan="1">121.0</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2</td><td rowspan="1" colspan="1">120.8</td><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">121.0</td></tr><tr><td rowspan="1" colspan="1">N1—C3—C2</td><td rowspan="1" colspan="1">124.4 (2)</td><td rowspan="1" colspan="1">C6—N2—N3</td><td rowspan="1" colspan="1">111.59 (13)</td></tr><tr><td rowspan="1" colspan="1">N1—C3—H3</td><td rowspan="1" colspan="1">117.8</td><td rowspan="1" colspan="1">C7—N3—N2</td><td rowspan="1" colspan="1">113.40 (14)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">117.8</td><td rowspan="1" colspan="1">C7—N3—Co1</td><td rowspan="1" colspan="1">113.97 (11)</td></tr><tr><td rowspan="1" colspan="1">C3—N1—C5</td><td rowspan="1" colspan="1">116.54 (18)</td><td rowspan="1" colspan="1">N2—N3—Co1</td><td rowspan="1" colspan="1">132.53 (10)</td></tr><tr><td rowspan="1" colspan="1">N1—C5—C4</td><td rowspan="1" colspan="1">123.60 (17)</td><td rowspan="1" colspan="1">C12—N4—C8</td><td rowspan="1" colspan="1">117.54 (15)</td></tr><tr><td rowspan="1" colspan="1">N1—C5—C6</td><td rowspan="1" colspan="1">113.95 (15)</td><td rowspan="1" colspan="1">C12—N4—Co1</td><td rowspan="1" colspan="1">126.96 (12)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6</td><td rowspan="1" colspan="1">122.44 (17)</td><td rowspan="1" colspan="1">C8—N4—Co1</td><td rowspan="1" colspan="1">115.44 (11)</td></tr><tr><td rowspan="1" colspan="1">N2—C6—C5</td><td rowspan="1" colspan="1">125.69 (15)</td><td rowspan="1" colspan="1">N6—N5—Co1</td><td rowspan="1" colspan="1">119.66 (14)</td></tr><tr><td rowspan="1" colspan="1">N2—C6—S1</td><td rowspan="1" colspan="1">114.57 (12)</td><td rowspan="1" colspan="1">N7—N6—N5</td><td rowspan="1" colspan="1">178.7 (2)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—S1</td><td rowspan="1" colspan="1">119.72 (13)</td><td rowspan="1" colspan="1">C7—S1—C6</td><td rowspan="1" colspan="1">86.85 (8)</td></tr><tr><td rowspan="1" colspan="1">N3—C7—C8</td><td rowspan="1" colspan="1">120.22 (15)</td><td rowspan="1" colspan="1">N5—Co1—N5<sup>i</sup></td><td rowspan="1" colspan="1">180.0</td></tr><tr><td rowspan="1" colspan="1">N3—C7—S1</td><td rowspan="1" colspan="1">113.57 (13)</td><td rowspan="1" colspan="1">N5—Co1—N3<sup>i</sup></td><td rowspan="1" colspan="1">90.73 (6)</td></tr><tr><td rowspan="1" colspan="1">C8—C7—S1</td><td rowspan="1" colspan="1">126.20 (12)</td><td rowspan="1" colspan="1">N5<sup>i</sup>—Co1—N3<sup>i</sup></td><td rowspan="1" colspan="1">89.27 (6)</td></tr><tr><td rowspan="1" colspan="1">N4—C8—C9</td><td rowspan="1" colspan="1">123.13 (16)</td><td rowspan="1" colspan="1">N5—Co1—N3</td><td rowspan="1" colspan="1">89.27 (6)</td></tr><tr><td rowspan="1" colspan="1">N4—C8—C7</td><td rowspan="1" colspan="1">113.46 (14)</td><td rowspan="1" colspan="1">N5<sup>i</sup>—Co1—N3</td><td rowspan="1" colspan="1">90.73 (6)</td></tr><tr><td rowspan="1" colspan="1">C9—C8—C7</td><td rowspan="1" colspan="1">123.40 (16)</td><td rowspan="1" colspan="1">N3<sup>i</sup>—Co1—N3</td><td rowspan="1" colspan="1">180.0</td></tr><tr><td rowspan="1" colspan="1">C10—C9—C8</td><td rowspan="1" colspan="1">118.44 (17)</td><td rowspan="1" colspan="1">N5—Co1—N4</td><td rowspan="1" colspan="1">90.35 (6)</td></tr><tr><td rowspan="1" colspan="1">C10—C9—H9</td><td rowspan="1" colspan="1">120.8</td><td rowspan="1" colspan="1">N5<sup>i</sup>—Co1—N4</td><td rowspan="1" colspan="1">89.65 (6)</td></tr><tr><td rowspan="1" colspan="1">C8—C9—H9</td><td rowspan="1" colspan="1">120.8</td><td rowspan="1" colspan="1">N3<sup>i</sup>—Co1—N4</td><td rowspan="1" colspan="1">103.24 (5)</td></tr><tr><td rowspan="1" colspan="1">C11—C10—C9</td><td rowspan="1" colspan="1">119.22 (16)</td><td rowspan="1" colspan="1">N3—Co1—N4</td><td rowspan="1" colspan="1">76.76 (5)</td></tr><tr><td rowspan="1" colspan="1">C11—C10—H10</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">N5—Co1—N4<sup>i</sup></td><td rowspan="1" colspan="1">89.65 (6)</td></tr><tr><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">N5<sup>i</sup>—Co1—N4<sup>i</sup></td><td rowspan="1" colspan="1">90.34 (6)</td></tr><tr><td rowspan="1" colspan="1">C10—C11—C12</td><td rowspan="1" colspan="1">119.01 (17)</td><td rowspan="1" colspan="1">N3<sup>i</sup>—Co1—N4<sup>i</sup></td><td rowspan="1" colspan="1">76.76 (5)</td></tr><tr><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">120.5</td><td rowspan="1" colspan="1">N3—Co1—N4<sup>i</sup></td><td rowspan="1" colspan="1">103.24 (5)</td></tr><tr><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">120.5</td><td rowspan="1" colspan="1">N4—Co1—N4<sup>i</sup></td><td rowspan="1" colspan="1">180.0</td></tr></table></table-wrap><p>Symmetry code: (i) −<italic>x</italic>, −<italic>y</italic>, −<italic>z</italic>.</p></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title><table-wrap position="anchor" id="d1e1913"><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">C2—H2···N6<sup>ii</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.59</td><td rowspan="1" colspan="1">3.432 (3)</td><td rowspan="1" colspan="1">151</td></tr><tr><td rowspan="1" colspan="1">C11—H11···N7<sup>iii</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.60</td><td rowspan="1" colspan="1">3.528 (3)</td><td rowspan="1" colspan="1">173</td></tr><tr><td rowspan="1" colspan="1">C10—H10···N1<sup>iv</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.63</td><td rowspan="1" colspan="1">3.438 (2)</td><td rowspan="1" colspan="1">146</td></tr></table></table-wrap><p>Symmetry codes: (ii) <italic>x</italic>+1, <italic>y</italic>+1, <italic>z</italic>; (iii) <italic>x</italic>−1, <italic>y</italic>, <italic>z</italic>; (iv) −<italic>x</italic>, <italic>y</italic>−1/2, −<italic>z</italic>+1/2.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Bentiss, F., Capet, F., Lagrenée, M., Saadi, M. & El Ammari, L. 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Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Farrugia, L. J. (2012). <italic>J. Appl. Cryst.</italic><bold>45</bold>, 849–854.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Kaase, D. & Klingele, J. (2014). <italic>Acta Cryst.</italic> E<bold>70</bold>, m252–m253.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Laachir, A., Bentiss, F., Guesmi, S., Saadi, M. & El Ammari, L. (2013). <italic>Acta Cryst.</italic> E<bold>69</bold>, m351–m352.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Laachir, A., Bentiss, F., Guesmi, S., Saadi, M. & El Ammari, L. (2015). <italic>Acta Cryst.</italic> E<bold>71</bold>, m24–m25.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Lebrini, M., Bentiss, F. & Lagrenée, M. (2005). <italic>J. Heterocycl. Chem.</italic><bold>42</bold>, 991–994.</mixed-citation></ref><ref id="bb11"><mixed-citation publication-type="other">Nath, J. K. & Baruah, J. B. (2012). <italic>Polyhedron</italic>, <bold>36</bold>, 1–5.</mixed-citation></ref><ref id="bb12"><mixed-citation publication-type="other">Ray, A., Rosair, G. M., Pilet, G., Dede, B., Gómez-García, C. J., Signorella, S., Bellú, S. & Mitra, S. (2011). <italic>Inorg. Chim. Acta</italic>, <bold>375</bold>, 20–30.</mixed-citation></ref><ref id="bb13"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref></ref-list></back><floats-group><fig id="fig1" position="float"><label>Figure 1</label><caption><p>The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as spheres of arbitrary radius. [Symmetry code: (i) −<italic>x</italic>, −<italic>y</italic>, −<italic>z</italic>.]</p></caption><graphic xlink:href="e-71-00452-fig1"></graphic></fig><fig id="fig2" position="float"><label>Figure 2</label><caption><p>Partial crystal packing of the title compound, showing intermolecular π–π interactions between pyridine rings (dashed green lines) and intermolecular C—H⋯N hydrogen bonds (dashed blue lines).</p></caption><graphic xlink:href="e-71-00452-fig2"></graphic></fig><table-wrap id="table1" position="float"><label>Table 1</label><caption><title>Hydrogen-bond geometry (, )</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 rowspan="1" colspan="1" align="left" valign="top">C2H2N6<sup>i</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.59</td><td rowspan="1" colspan="1" align="left" valign="top">3.432(3)</td><td rowspan="1" colspan="1" align="left" valign="top">151</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C11H11N7<sup>ii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.60</td><td rowspan="1" colspan="1" align="left" valign="top">3.528(3)</td><td rowspan="1" colspan="1" align="left" valign="top">173</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C10H10N1<sup>iii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.93</td><td rowspan="1" colspan="1" align="left" valign="top">2.63</td><td rowspan="1" colspan="1" align="left" valign="top">3.438(2)</td><td rowspan="1" colspan="1" align="left" valign="top">146</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-71-00452-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-71-00452-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iii) <inline-formula><inline-graphic xlink:href="e-71-00452-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap><table-wrap id="table2" position="float"><label>Table 2</label><caption><title>Experimental details</title></caption><table frame="hsides" rules="groups"><tbody valign="top"><tr><td rowspan="1" colspan="2" align="left" valign="top">Crystal data</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Chemical formula</td><td rowspan="1" colspan="1" align="left" valign="top">[Co(N<sub>3</sub>)<sub>2</sub>(C<sub>12</sub>H<sub>8</sub>N<sub>4</sub>S)<sub>2</sub>]</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>M</italic><sub>r</sub></td><td rowspan="1" colspan="1" align="left" valign="top">623.56</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal system, space group</td><td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>2<sub>1</sub>/<italic>c</italic></td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Temperature (K)</td><td rowspan="1" colspan="1" align="left" valign="top">296</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>a</italic>, <italic>b</italic>, <italic>c</italic> ()</td><td rowspan="1" colspan="1" align="left" valign="top">7.8004(3), 8.2439(3), 20.3222(8)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"> ()</td><td rowspan="1" colspan="1" align="left" valign="top">92.910(2)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>V</italic> (<sup>3</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">1305.15(9)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>Z</italic></td><td rowspan="1" colspan="1" align="left" valign="top">2</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Radiation type</td><td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic></td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"> (mm<sup>1</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">0.86</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal size (mm)</td><td rowspan="1" colspan="1" align="left" valign="top">0.39 0.31 0.18</td></tr><tr><td rowspan="1" colspan="2" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="2" align="left" valign="top">Data collection</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Diffractometer</td><td rowspan="1" colspan="1" align="left" valign="top">Bruker APEXII CCD</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Absorption correction</td><td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>SADABS</italic>; Bruker, 2009<xref ref-type="bibr" rid="bb5"> ▸</xref>)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>T</italic><sub>min</sub>, <italic>T</italic><sub>max</sub></td><td rowspan="1" colspan="1" align="left" valign="top">0.640, 0.747</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">No. of measured, independent and observed [<italic>I</italic> > 2(<italic>I</italic>)] reflections</td><td rowspan="1" colspan="1" align="left" valign="top">27415, 3667, 2884</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic><sub>int</sub></td><td rowspan="1" colspan="1" align="left" valign="top">0.043</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">(sin /)<sub>max</sub> (<sup>1</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">0.694</td></tr><tr><td rowspan="1" colspan="2" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="2" align="left" valign="top">Refinement</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2(<italic>F</italic><sup>2</sup>)], <italic>wR</italic>(<italic>F</italic><sup>2</sup>), <italic>S</italic></td><td rowspan="1" colspan="1" align="left" valign="top">0.035, 0.088, 1.03</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">No. of reflections</td><td rowspan="1" colspan="1" align="left" valign="top">3667</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">No. of parameters</td><td rowspan="1" colspan="1" align="left" valign="top">187</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">H-atom treatment</td><td rowspan="1" colspan="1" align="left" valign="top">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><sub>max</sub>, <sub>min</sub> (e <sup>3</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">0.70, 0.26</td></tr></tbody></table><table-wrap-foot><p>Computer programs: <italic>APEX2</italic> and <italic>SAINT</italic> (Bruker, 2009<xref ref-type="bibr" rid="bb5"> ▸</xref>), <italic>SHELXS97</italic> and <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb13"> ▸</xref>), <italic>ORTEP-3 for Windows</italic> and <italic>WinGX</italic> (Farrugia, 2012<xref ref-type="bibr" rid="bb6"> ▸</xref>).</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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