N′-[(1E)-3-Bromo-5-chloro-2-hydroxybenzylidene]-4-tert-butylbenzohydrazide ethanol monosolvate
Identifieur interne : 000A26 ( Pmc/Corpus ); précédent : 000A25; suivant : 000A27N′-[(1E)-3-Bromo-5-chloro-2-hydroxybenzylidene]-4-tert-butylbenzohydrazide ethanol monosolvate
Auteurs : A. Thirugnanasundar ; K. Parthipan ; V. S. Xavier Anthonisamy ; G. Chakkaravarthi ; G. RajagopalSource :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2011.
Abstract
In the title compound, C18H18BrClN2O2·C2H6O, the hydroxy group forms an intramolecular O—H⋯N hydrogen bond, which influences the conformation of the Shiff base molecule, where the two aromatic rings form a dihedral angle of 21.67 (8)°. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds link two Shiff base molecules and two solvent molecules into a centrosymmetric heterotetramer. Weak intermolecular C—H⋯O interactions link further tetramers related by translation along the
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DOI: 10.1107/S160053681104027X
PubMed: 22219898
PubMed Central: 3247593
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en"><italic>N</italic>′-[(1<italic>E</italic>)-3-Bromo-5-chloro-2-hydroxybenzylidene]-4-<italic>tert</italic>-butylbenzohydrazide ethanol monosolvate</title><author><name sortKey="Thirugnanasundar, A" sort="Thirugnanasundar, A" uniqKey="Thirugnanasundar A" first="A." last="Thirugnanasundar">A. Thirugnanasundar</name><affiliation><nlm:aff id="a">Department of Chemistry, Velalar College of Engineering and Technology, Erode 638 009,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Parthipan, K" sort="Parthipan, K" uniqKey="Parthipan K" first="K." last="Parthipan">K. Parthipan</name><affiliation><nlm:aff id="b">Department of Chemistry, Pondicherry University, Pondicherry 605014,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Anthonisamy, V S Xavier" sort="Anthonisamy, V S Xavier" uniqKey="Anthonisamy V" first="V. S. Xavier" last="Anthonisamy">V. S. Xavier Anthonisamy</name><affiliation><nlm:aff id="c">Department of Chemistry, Government Arts College, Melur 625 106,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Chakkaravarthi, G" sort="Chakkaravarthi, G" uniqKey="Chakkaravarthi G" first="G." last="Chakkaravarthi">G. Chakkaravarthi</name><affiliation><nlm:aff id="d">Department of Physics, CPCL Polytechnic College, Chennai 600 068,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Rajagopal, G" sort="Rajagopal, G" uniqKey="Rajagopal G" first="G." last="Rajagopal">G. Rajagopal</name><affiliation><nlm:aff id="c">Department of Chemistry, Government Arts College, Melur 625 106,<country>India</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">22219898</idno><idno type="pmc">3247593</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247593</idno><idno type="RBID">PMC:3247593</idno><idno type="doi">10.1107/S160053681104027X</idno><date when="2011">2011</date><idno type="wicri:Area/Pmc/Corpus">000A26</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A26</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main"><italic>N</italic>′-[(1<italic>E</italic>)-3-Bromo-5-chloro-2-hydroxybenzylidene]-4-<italic>tert</italic>-butylbenzohydrazide ethanol monosolvate</title><author><name sortKey="Thirugnanasundar, A" sort="Thirugnanasundar, A" uniqKey="Thirugnanasundar A" first="A." last="Thirugnanasundar">A. Thirugnanasundar</name><affiliation><nlm:aff id="a">Department of Chemistry, Velalar College of Engineering and Technology, Erode 638 009,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Parthipan, K" sort="Parthipan, K" uniqKey="Parthipan K" first="K." last="Parthipan">K. Parthipan</name><affiliation><nlm:aff id="b">Department of Chemistry, Pondicherry University, Pondicherry 605014,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Anthonisamy, V S Xavier" sort="Anthonisamy, V S Xavier" uniqKey="Anthonisamy V" first="V. S. Xavier" last="Anthonisamy">V. S. Xavier Anthonisamy</name><affiliation><nlm:aff id="c">Department of Chemistry, Government Arts College, Melur 625 106,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Chakkaravarthi, G" sort="Chakkaravarthi, G" uniqKey="Chakkaravarthi G" first="G." last="Chakkaravarthi">G. Chakkaravarthi</name><affiliation><nlm:aff id="d">Department of Physics, CPCL Polytechnic College, Chennai 600 068,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Rajagopal, G" sort="Rajagopal, G" uniqKey="Rajagopal G" first="G." last="Rajagopal">G. Rajagopal</name><affiliation><nlm:aff id="c">Department of Chemistry, Government Arts College, Melur 625 106,<country>India</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="2011">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>In the title compound, C<sub>18</sub>H<sub>18</sub>BrClN<sub>2</sub>O<sub>2</sub>·C<sub>2</sub>H<sub>6</sub>O, the hydroxy group forms an intramolecular O—H⋯N hydrogen bond, which influences the conformation of the Shiff base molecule, where the two aromatic rings form a dihedral angle of 21.67 (8)°. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds link two Shiff base molecules and two solvent molecules into a centrosymmetric heterotetramer. Weak intermolecular C—H⋯O interactions link further tetramers related by translation along the <italic>a</italic> axis into chains.</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></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="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">22219898</article-id><article-id pub-id-type="pmc">3247593</article-id><article-id pub-id-type="publisher-id">cv5157</article-id><article-id pub-id-type="doi">10.1107/S160053681104027X</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S160053681104027X</article-id><article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject></subj-group></article-categories><title-group><article-title><italic>N</italic>′-[(1<italic>E</italic>)-3-Bromo-5-chloro-2-hydroxybenzylidene]-4-<italic>tert</italic>-butylbenzohydrazide ethanol monosolvate</article-title><alt-title><italic>C<sub>18</sub>H<sub>18</sub>BrClN<sub>2</sub>O<sub>2</sub>·C<sub>2</sub>H<sub>6</sub>O</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Thirugnanasundar</surname><given-names>A.</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Parthipan</surname><given-names>K.</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><name><surname>Anthonisamy</surname><given-names>V. S. Xavier</given-names></name><xref ref-type="aff" rid="c">c</xref></contrib><contrib contrib-type="author"><name><surname>Chakkaravarthi</surname><given-names>G.</given-names></name><xref ref-type="aff" rid="d">d</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><contrib contrib-type="author"><name><surname>Rajagopal</surname><given-names>G.</given-names></name><xref ref-type="aff" rid="c">c</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><aff id="a"><label>a</label>Department of Chemistry, Velalar College of Engineering and Technology, Erode 638 009,<country>India</country></aff><aff id="b"><label>b</label>Department of Chemistry, Pondicherry University, Pondicherry 605014,<country>India</country></aff><aff id="c"><label>c</label>Department of Chemistry, Government Arts College, Melur 625 106,<country>India</country></aff><aff id="d"><label>d</label>Department of Physics, CPCL Polytechnic College, Chennai 600 068,<country>India</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>chakkaravarthi_2005@yahoo.com</email>, <email>rajagopal18@yahoo.com</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>11</month><year>2011</year></pub-date><pub-date pub-type="epub"><day>05</day><month>10</month><year>2011</year></pub-date><pub-date pub-type="pmc-release"><day>05</day><month>10</month><year>2011</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>67</volume><issue>Pt 11</issue><issue-id pub-id-type="publisher-id">e111100</issue-id><fpage>o2857</fpage><lpage>o2857</lpage><history><date date-type="received"><day>20</day><month>9</month><year>2011</year></date><date date-type="accepted"><day>29</day><month>9</month><year>2011</year></date></history><permissions><copyright-statement>© Thirugnanasundar et al. 2011</copyright-statement><copyright-year>2011</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/S160053681104027X">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>In the title compound, C<sub>18</sub>H<sub>18</sub>BrClN<sub>2</sub>O<sub>2</sub>·C<sub>2</sub>H<sub>6</sub>O, the hydroxy group forms an intramolecular O—H⋯N hydrogen bond, which influences the conformation of the Shiff base molecule, where the two aromatic rings form a dihedral angle of 21.67 (8)°. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds link two Shiff base molecules and two solvent molecules into a centrosymmetric heterotetramer. Weak intermolecular C—H⋯O interactions link further tetramers related by translation along the <italic>a</italic> axis into chains.</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature</title><p>For the biological activity of Schiff base derivatives, see: Dao <italic>et al.</italic> (2000<xref ref-type="bibr" rid="bb2"> ▶</xref>); Karthikeyan <italic>et al.</italic> (2006<xref ref-type="bibr" rid="bb4"> ▶</xref>); Prabhakaran <italic>et al.</italic> (2006<xref ref-type="bibr" rid="bb5"> ▶</xref>); Shivakumar <italic>et al.</italic> (2008<xref ref-type="bibr" rid="bb8"> ▶</xref>). For related structures, see: Fun <italic>et al.</italic> (2008<xref ref-type="bibr" rid="bb3"> ▶</xref>); Thirugnanasundar <italic>et al.</italic> (2011<xref ref-type="bibr" rid="bb10"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-67-o2857-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>C<sub>18</sub>H<sub>18</sub>BrClN<sub>2</sub>O<sub>2</sub>·C<sub>2</sub>H<sub>6</sub>O</p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 455.77</p></list-item><list-item><p>Triclinic, <inline-formula><inline-graphic xlink:href="e-67-o2857-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 9.2478 (4) Å</p></list-item><list-item><p><italic>b</italic> = 9.4057 (4) Å</p></list-item><list-item><p><italic>c</italic> = 12.7838 (5) Å</p></list-item><list-item><p>α = 78.811 (2)°</p></list-item><list-item><p>β = 79.235 (1)°</p></list-item><list-item><p>γ = 79.469 (2)°</p></list-item><list-item><p><italic>V</italic> = 1059.17 (8) 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 = 2.09 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 295 K</p></list-item><list-item><p>0.26 × 0.22 × 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 diffractometer</p></list-item><list-item><p>Absorption correction: multi-scan (<italic>SADABS</italic>; Sheldrick, 1996<xref ref-type="bibr" rid="bb6"> ▶</xref>) <italic>T</italic><sub>min</sub> = 0.613, <italic>T</italic><sub>max</sub> = 0.680</p></list-item><list-item><p>27712 measured reflections</p></list-item><list-item><p>6728 independent reflections</p></list-item><list-item><p>3460 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.033</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>)] = 0.052</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.180</p></list-item><list-item><p><italic>S</italic> = 1.03</p></list-item><list-item><p>6728 reflections</p></list-item><list-item><p>248 parameters</p></list-item><list-item><p>1 restraint</p></list-item><list-item><p>H-atom parameters constrained</p></list-item><list-item><p>Δρ<sub>max</sub> = 0.60 e Å<sup>−3</sup></p></list-item><list-item><p>Δρ<sub>min</sub> = −0.63 e Å<sup>−3</sup></p></list-item></list></p></sec></sec><sec id="d5e523"><title></title><p>Data collection: <italic>APEX2</italic> (Bruker, 2004<xref ref-type="bibr" rid="bb1"> ▶</xref>); cell refinement: <italic>SAINT</italic> (Bruker, 2004<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="bb7"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb7"> ▶</xref>); molecular graphics: <italic>PLATON</italic> (Spek, 2009<xref ref-type="bibr" rid="bb9"> ▶</xref>); software used to prepare material for publication: <italic>SHELXL97</italic>.</p></sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data" xlink:href="e-67-o2857-sup1.cif" position="float" xlink:type="simple"><p>Crystal structure: contains datablock(s) global, I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S160053681104027X/cv5157sup1.cif">10.1107/S160053681104027X/cv5157sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-67-o2857-sup1.cif" position="float" xlink:type="simple"></media></supplementary-material><supplementary-material content-type="local-data" xlink:href="e-67-o2857-Isup2.hkl" position="float" xlink:type="simple"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S160053681104027X/cv5157Isup2.hkl">10.1107/S160053681104027X/cv5157Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-67-o2857-Isup2.hkl" position="float" xlink:type="simple"></media></supplementary-material><supplementary-material content-type="local-data" xlink:href="e-67-o2857-Isup3.cml" mimetype="chemical" mime-subtype="x-cml" position="float" xlink:type="simple"><p>Supplementary material file. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S160053681104027X/cv5157Isup3.cml">10.1107/S160053681104027X/cv5157Isup3.cml</ext-link></p></supplementary-material><supplementary-material position="float" xlink:type="simple"><p>Additional supplementary materials: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?cv5157&file=cv5157sup0.html&mime=text/html" xlink:type="simple"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?cv5157sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?cv5157&checkcif=yes" xlink:type="simple">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?cv5157">CV5157</ext-link>).</p></fn></fn-group><ack><p>The authors acknowledge SAIF, IIT, Madras, for the X-ray data collection.</p></ack><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>Comment </title><p>Schiff base compounds have been widely used as versatile ligands in
coordination chemistry (Shivakumar <italic>et al.</italic>, 2008; Prabhakaran
<italic>et al.</italic>, 2006). Schiff bases are also known to exhibit
anticancer,
antibacterial and antifungal activities (Dao <italic>et al.</italic>, 2000;
Karthikeyan
<italic>et al.</italic>, 2006). Herewith we present the title compound (I), which
is a new Schiff base.</p><p>In (I) (Fig. 1), the geometric parameters
are comparable with the those reported for similar structures
( Fun <italic>et al.</italic>, 2008;
Thirugnanasundar <italic>et al.</italic>, 2011).
The dihedral angle between the two aromatic
rings is 21.67 (8)°.
Intermolecular N—H···O and O—H···O hydrogen bonds (Table 1)
link two Shiff
base molecules and two solvent molecules into centrosymmetric
tetramer (Fig. 2).
Weak intermolecular C—H···O interactions (Table 1) link further the
tetramers related by translation along axis <italic>a</italic> into chains.</p></sec><sec id="experimental"><title>Experimental </title><p>4-<italic>tert</italic>-Butylbenzoichydrazide (5 mmol) was dissolved in 20 mL
of dry ethanol with stirring and warming over a period of 10 min.
To the warm hydrazide solution, 3-bromo-5-chloro salicylaldehyde
(5 mmol) in 20 mL of dry ethanol was added and the mixture was
stirred and slowly refluxed for 2 h. The mixture was then cooled
down to room temperature when pale yellow crystalline compound
precipitated. The compound was collected by filtration, washed
with cold ethanol and dried in vacuum. Single crystals suitable
for the X-ray diffraction were obtained by slow evaporation of
a solution of the title compound in ethanol at room temperature.
Melting Point: 498 - 500 K.</p></sec><sec id="refinement"><title>Refinement </title><p>All H atoms were positioned geometrically [C—H = 0.93-0.97)Å,
O—H = 0.82 Å, N—H = 0.86 Å] and allowed to ride on their
parent atoms, with U<sub>iso</sub>(H) = 1.2-1.5 U<sub>eq</sub> of the parent atom.
The bond distance C19-C20 was restrained to 1.540 (1)Å.</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. Dashed lines denote hydrogen bonds.</p></caption><graphic xlink:href="e-67-o2857-fig1"></graphic></fig><fig id="Fap2"><label>Fig. 2.</label><caption><p>Hydrogen-bonded (dashed lines) tetramer in (I), viewed down a axis. H atoms not involved in hydrogen bonding have been omitted.</p></caption><graphic xlink:href="e-67-o2857-fig2"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e130"><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">C<sub>18</sub>H<sub>18</sub>BrClN<sub>2</sub>O<sub>2</sub>·C<sub>2</sub>H<sub>6</sub>O</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> = 455.77</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 468</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> = 1.429 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> = 9.2478 (4) Å</td><td rowspan="1" colspan="1">Cell parameters from 5983 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 9.4057 (4) Å</td><td rowspan="1" colspan="1">θ = 2.2–25.3°</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 12.7838 (5) Å</td><td rowspan="1" colspan="1">µ = 2.09 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">α = 78.811 (2)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 295 K</td></tr><tr><td rowspan="1" colspan="1">β = 79.235 (1)°</td><td rowspan="1" colspan="1">Block, pale yellow</td></tr><tr><td rowspan="1" colspan="1">γ = 79.469 (2)°</td><td rowspan="1" colspan="1">0.26 × 0.22 × 0.20 mm</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1059.17 (8) 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="d1e274"><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 diffractometer</td><td rowspan="1" colspan="1">6728 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">3460 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">graphite</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.033</td></tr><tr><td rowspan="1" colspan="1">ω and φ scans</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 31.1°, θ<sub>min</sub> = 2.3°</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>SADABS</italic>; Sheldrick, 1996)</td><td rowspan="1" colspan="1"><italic>h</italic> = −13→13</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.613, <italic>T</italic><sub>max</sub> = 0.680</td><td rowspan="1" colspan="1"><italic>k</italic> = −13→13</td></tr><tr><td rowspan="1" colspan="1">27712 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −18→18</td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e391"><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>)] = 0.052</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>) = 0.180</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>) + (0.0879<italic>P</italic>)<sup>2</sup> + 0.2447<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">6728 reflections</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1">248 parameters</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.60 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">1 restraint</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.63 e Å<sup>−</sup><sup>3</sup></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="d1e550"><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">Br1</td><td rowspan="1" colspan="1">0.93954 (5)</td><td rowspan="1" colspan="1">0.98169 (6)</td><td rowspan="1" colspan="1">0.84703 (3)</td><td rowspan="1" colspan="1">0.1019 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Cl1</td><td rowspan="1" colspan="1">0.49673 (11)</td><td rowspan="1" colspan="1">1.20251 (9)</td><td rowspan="1" colspan="1">0.60211 (8)</td><td rowspan="1" colspan="1">0.0842 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">1.0463 (2)</td><td rowspan="1" colspan="1">0.8013 (2)</td><td rowspan="1" colspan="1">0.67203 (17)</td><td rowspan="1" colspan="1">0.0626 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">1.0757</td><td rowspan="1" colspan="1">0.7517</td><td rowspan="1" colspan="1">0.6239</td><td rowspan="1" colspan="1">0.094*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">1.2797 (2)</td><td rowspan="1" colspan="1">0.5219 (2)</td><td rowspan="1" colspan="1">0.52053 (15)</td><td rowspan="1" colspan="1">0.0637 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">1.0370 (2)</td><td rowspan="1" colspan="1">0.7096 (2)</td><td rowspan="1" colspan="1">0.49638 (17)</td><td rowspan="1" colspan="1">0.0473 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">1.1026 (2)</td><td rowspan="1" colspan="1">0.6271 (2)</td><td rowspan="1" colspan="1">0.41810 (17)</td><td rowspan="1" colspan="1">0.0465 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2</td><td rowspan="1" colspan="1">1.0646</td><td rowspan="1" colspan="1">0.6326</td><td rowspan="1" colspan="1">0.3607</td><td rowspan="1" colspan="1">0.056*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.8540 (3)</td><td rowspan="1" colspan="1">0.8951 (3)</td><td rowspan="1" colspan="1">0.5612 (2)</td><td rowspan="1" colspan="1">0.0467 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.9213 (3)</td><td rowspan="1" colspan="1">0.8912 (3)</td><td rowspan="1" colspan="1">0.6516 (2)</td><td rowspan="1" colspan="1">0.0484 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.8529 (3)</td><td rowspan="1" colspan="1">0.9868 (3)</td><td rowspan="1" colspan="1">0.7243 (2)</td><td rowspan="1" colspan="1">0.0549 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.7247 (3)</td><td rowspan="1" colspan="1">1.0821 (3)</td><td rowspan="1" colspan="1">0.7087 (2)</td><td rowspan="1" colspan="1">0.0575 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.6820</td><td rowspan="1" colspan="1">1.1453</td><td rowspan="1" colspan="1">0.7575</td><td rowspan="1" colspan="1">0.069*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.6601 (3)</td><td rowspan="1" colspan="1">1.0831 (3)</td><td rowspan="1" colspan="1">0.6197 (2)</td><td rowspan="1" colspan="1">0.0560 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.7235 (3)</td><td rowspan="1" colspan="1">0.9919 (3)</td><td rowspan="1" colspan="1">0.5463 (2)</td><td rowspan="1" colspan="1">0.0545 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6</td><td rowspan="1" colspan="1">0.6791</td><td rowspan="1" colspan="1">0.9948</td><td rowspan="1" colspan="1">0.4862</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.9190 (3)</td><td rowspan="1" colspan="1">0.8017 (3)</td><td rowspan="1" colspan="1">0.4805 (2)</td><td rowspan="1" colspan="1">0.0504 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7</td><td rowspan="1" colspan="1">0.8762</td><td rowspan="1" colspan="1">0.8085</td><td rowspan="1" colspan="1">0.4191</td><td rowspan="1" colspan="1">0.060*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">1.2312 (3)</td><td rowspan="1" colspan="1">0.5359 (3)</td><td rowspan="1" colspan="1">0.43593 (19)</td><td rowspan="1" colspan="1">0.0448 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">1.3105 (3)</td><td rowspan="1" colspan="1">0.4581 (2)</td><td rowspan="1" colspan="1">0.34618 (19)</td><td rowspan="1" colspan="1">0.0413 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">1.2420 (3)</td><td rowspan="1" colspan="1">0.4292 (3)</td><td rowspan="1" colspan="1">0.2672 (2)</td><td rowspan="1" colspan="1">0.0461 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">1.1405</td><td rowspan="1" colspan="1">0.4603</td><td rowspan="1" colspan="1">0.2676</td><td rowspan="1" colspan="1">0.055*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">1.3245 (3)</td><td rowspan="1" colspan="1">0.3540 (3)</td><td rowspan="1" colspan="1">0.1874 (2)</td><td rowspan="1" colspan="1">0.0477 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">1.2765</td><td rowspan="1" colspan="1">0.3344</td><td rowspan="1" colspan="1">0.1353</td><td rowspan="1" colspan="1">0.057*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">1.4758 (3)</td><td rowspan="1" colspan="1">0.3071 (2)</td><td rowspan="1" colspan="1">0.1826 (2)</td><td rowspan="1" colspan="1">0.0444 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">1.5416 (3)</td><td rowspan="1" colspan="1">0.3359 (3)</td><td rowspan="1" colspan="1">0.2627 (2)</td><td rowspan="1" colspan="1">0.0538 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">1.6432</td><td rowspan="1" colspan="1">0.3051</td><td rowspan="1" colspan="1">0.2620</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">1.4614 (3)</td><td rowspan="1" colspan="1">0.4091 (3)</td><td rowspan="1" colspan="1">0.3443 (2)</td><td rowspan="1" colspan="1">0.0543 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H14</td><td rowspan="1" colspan="1">1.5090</td><td rowspan="1" colspan="1">0.4254</td><td rowspan="1" colspan="1">0.3980</td><td rowspan="1" colspan="1">0.065*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">1.5690 (3)</td><td rowspan="1" colspan="1">0.2267 (3)</td><td rowspan="1" colspan="1">0.0933 (2)</td><td rowspan="1" colspan="1">0.0539 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">1.4789 (5)</td><td rowspan="1" colspan="1">0.2141 (5)</td><td rowspan="1" colspan="1">0.0085 (3)</td><td rowspan="1" colspan="1">0.0977 (13)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16A</td><td rowspan="1" colspan="1">1.4379</td><td rowspan="1" colspan="1">0.3103</td><td rowspan="1" colspan="1">−0.0238</td><td rowspan="1" colspan="1">0.146*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16B</td><td rowspan="1" colspan="1">1.3995</td><td rowspan="1" colspan="1">0.1593</td><td rowspan="1" colspan="1">0.0418</td><td rowspan="1" colspan="1">0.146*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16C</td><td rowspan="1" colspan="1">1.5423</td><td rowspan="1" colspan="1">0.1646</td><td rowspan="1" colspan="1">−0.0461</td><td rowspan="1" colspan="1">0.146*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">1.7001 (5)</td><td rowspan="1" colspan="1">0.3051 (4)</td><td rowspan="1" colspan="1">0.0402 (3)</td><td rowspan="1" colspan="1">0.0918 (13)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17A</td><td rowspan="1" colspan="1">1.6648</td><td rowspan="1" colspan="1">0.4066</td><td rowspan="1" colspan="1">0.0164</td><td rowspan="1" colspan="1">0.138*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17B</td><td rowspan="1" colspan="1">1.7520</td><td rowspan="1" colspan="1">0.2610</td><td rowspan="1" colspan="1">−0.0208</td><td rowspan="1" colspan="1">0.138*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H17C</td><td rowspan="1" colspan="1">1.7664</td><td rowspan="1" colspan="1">0.2971</td><td rowspan="1" colspan="1">0.0912</td><td rowspan="1" colspan="1">0.138*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">1.6298 (4)</td><td rowspan="1" colspan="1">0.0714 (3)</td><td rowspan="1" colspan="1">0.1443 (3)</td><td rowspan="1" colspan="1">0.0780 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18A</td><td rowspan="1" colspan="1">1.6936</td><td rowspan="1" colspan="1">0.0220</td><td rowspan="1" colspan="1">0.0898</td><td rowspan="1" colspan="1">0.117*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18B</td><td rowspan="1" colspan="1">1.5484</td><td rowspan="1" colspan="1">0.0184</td><td rowspan="1" colspan="1">0.1756</td><td rowspan="1" colspan="1">0.117*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H18C</td><td rowspan="1" colspan="1">1.6854</td><td rowspan="1" colspan="1">0.0765</td><td rowspan="1" colspan="1">0.1995</td><td rowspan="1" colspan="1">0.117*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.8792 (3)</td><td rowspan="1" colspan="1">0.6125 (3)</td><td rowspan="1" colspan="1">0.29413 (18)</td><td rowspan="1" colspan="1">0.0786 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.8295</td><td rowspan="1" colspan="1">0.5667</td><td rowspan="1" colspan="1">0.3451</td><td rowspan="1" colspan="1">0.118*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.9211 (6)</td><td rowspan="1" colspan="1">0.6211 (10)</td><td rowspan="1" colspan="1">0.1011 (4)</td><td rowspan="1" colspan="1">0.163 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19A</td><td rowspan="1" colspan="1">0.9967</td><td rowspan="1" colspan="1">0.6814</td><td rowspan="1" colspan="1">0.0944</td><td rowspan="1" colspan="1">0.244*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19B</td><td rowspan="1" colspan="1">0.8696</td><td rowspan="1" colspan="1">0.6507</td><td rowspan="1" colspan="1">0.0400</td><td rowspan="1" colspan="1">0.244*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H19C</td><td rowspan="1" colspan="1">0.9665</td><td rowspan="1" colspan="1">0.5204</td><td rowspan="1" colspan="1">0.1040</td><td rowspan="1" colspan="1">0.244*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.8100 (5)</td><td rowspan="1" colspan="1">0.6384 (8)</td><td rowspan="1" colspan="1">0.2050 (3)</td><td rowspan="1" colspan="1">0.1222 (18)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H20A</td><td rowspan="1" colspan="1">0.7549</td><td rowspan="1" colspan="1">0.7370</td><td rowspan="1" colspan="1">0.1978</td><td rowspan="1" colspan="1">0.147*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H20B</td><td rowspan="1" colspan="1">0.7393</td><td rowspan="1" colspan="1">0.5705</td><td rowspan="1" colspan="1">0.2149</td><td rowspan="1" colspan="1">0.147*</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="d1e1208"><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">Br1</td><td rowspan="1" colspan="1">0.0838 (3)</td><td rowspan="1" colspan="1">0.1505 (4)</td><td rowspan="1" colspan="1">0.0874 (3)</td><td rowspan="1" colspan="1">0.0068 (3)</td><td rowspan="1" colspan="1">−0.0185 (2)</td><td rowspan="1" colspan="1">−0.0770 (3)</td></tr><tr><td rowspan="1" colspan="1">Cl1</td><td rowspan="1" colspan="1">0.0797 (6)</td><td rowspan="1" colspan="1">0.0691 (5)</td><td rowspan="1" colspan="1">0.0899 (6)</td><td rowspan="1" colspan="1">0.0249 (4)</td><td rowspan="1" colspan="1">−0.0068 (5)</td><td rowspan="1" colspan="1">−0.0198 (4)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0522 (11)</td><td rowspan="1" colspan="1">0.0749 (12)</td><td rowspan="1" colspan="1">0.0641 (12)</td><td rowspan="1" colspan="1">0.0052 (9)</td><td rowspan="1" colspan="1">−0.0073 (9)</td><td rowspan="1" colspan="1">−0.0354 (10)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0541 (11)</td><td rowspan="1" colspan="1">0.0963 (15)</td><td rowspan="1" colspan="1">0.0461 (10)</td><td rowspan="1" colspan="1">−0.0032 (10)</td><td rowspan="1" colspan="1">−0.0084 (9)</td><td rowspan="1" colspan="1">−0.0323 (10)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0503 (12)</td><td rowspan="1" colspan="1">0.0485 (11)</td><td rowspan="1" colspan="1">0.0446 (11)</td><td rowspan="1" colspan="1">−0.0085 (9)</td><td rowspan="1" colspan="1">0.0045 (9)</td><td rowspan="1" colspan="1">−0.0216 (9)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.0493 (12)</td><td rowspan="1" colspan="1">0.0500 (11)</td><td rowspan="1" colspan="1">0.0411 (11)</td><td rowspan="1" colspan="1">−0.0020 (9)</td><td rowspan="1" colspan="1">0.0002 (9)</td><td rowspan="1" colspan="1">−0.0220 (9)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0482 (13)</td><td rowspan="1" colspan="1">0.0412 (12)</td><td rowspan="1" colspan="1">0.0482 (14)</td><td rowspan="1" colspan="1">−0.0070 (10)</td><td rowspan="1" colspan="1">0.0069 (11)</td><td rowspan="1" colspan="1">−0.0151 (10)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0495 (14)</td><td rowspan="1" colspan="1">0.0473 (13)</td><td rowspan="1" colspan="1">0.0482 (14)</td><td rowspan="1" colspan="1">−0.0119 (11)</td><td rowspan="1" colspan="1">0.0062 (11)</td><td rowspan="1" colspan="1">−0.0169 (11)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0543 (15)</td><td rowspan="1" colspan="1">0.0617 (15)</td><td rowspan="1" colspan="1">0.0511 (15)</td><td rowspan="1" colspan="1">−0.0137 (12)</td><td rowspan="1" colspan="1">0.0077 (12)</td><td rowspan="1" colspan="1">−0.0259 (12)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0598 (17)</td><td rowspan="1" colspan="1">0.0504 (14)</td><td rowspan="1" colspan="1">0.0588 (16)</td><td rowspan="1" colspan="1">−0.0089 (12)</td><td rowspan="1" colspan="1">0.0159 (13)</td><td rowspan="1" colspan="1">−0.0242 (12)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0571 (16)</td><td rowspan="1" colspan="1">0.0425 (13)</td><td rowspan="1" colspan="1">0.0598 (17)</td><td rowspan="1" colspan="1">0.0001 (11)</td><td rowspan="1" colspan="1">0.0065 (13)</td><td rowspan="1" colspan="1">−0.0101 (11)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0605 (17)</td><td rowspan="1" colspan="1">0.0486 (13)</td><td rowspan="1" colspan="1">0.0510 (15)</td><td rowspan="1" colspan="1">−0.0019 (12)</td><td rowspan="1" colspan="1">−0.0039 (12)</td><td rowspan="1" colspan="1">−0.0104 (11)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0589 (16)</td><td rowspan="1" colspan="1">0.0480 (13)</td><td rowspan="1" colspan="1">0.0443 (13)</td><td rowspan="1" colspan="1">−0.0057 (11)</td><td rowspan="1" colspan="1">−0.0001 (11)</td><td rowspan="1" colspan="1">−0.0176 (11)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0428 (13)</td><td rowspan="1" colspan="1">0.0531 (13)</td><td rowspan="1" colspan="1">0.0409 (13)</td><td rowspan="1" colspan="1">−0.0103 (10)</td><td rowspan="1" colspan="1">0.0002 (10)</td><td rowspan="1" colspan="1">−0.0170 (10)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0417 (12)</td><td rowspan="1" colspan="1">0.0429 (11)</td><td rowspan="1" colspan="1">0.0392 (12)</td><td rowspan="1" colspan="1">−0.0056 (9)</td><td rowspan="1" colspan="1">−0.0007 (9)</td><td rowspan="1" colspan="1">−0.0129 (9)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0396 (12)</td><td rowspan="1" colspan="1">0.0534 (13)</td><td rowspan="1" colspan="1">0.0459 (13)</td><td rowspan="1" colspan="1">0.0008 (10)</td><td rowspan="1" colspan="1">−0.0040 (10)</td><td rowspan="1" colspan="1">−0.0201 (11)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0468 (14)</td><td rowspan="1" colspan="1">0.0540 (13)</td><td rowspan="1" colspan="1">0.0447 (13)</td><td rowspan="1" colspan="1">0.0002 (10)</td><td rowspan="1" colspan="1">−0.0079 (11)</td><td rowspan="1" colspan="1">−0.0208 (11)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0454 (13)</td><td rowspan="1" colspan="1">0.0399 (11)</td><td rowspan="1" colspan="1">0.0456 (13)</td><td rowspan="1" colspan="1">−0.0036 (9)</td><td rowspan="1" colspan="1">0.0018 (10)</td><td rowspan="1" colspan="1">−0.0129 (10)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0358 (12)</td><td rowspan="1" colspan="1">0.0667 (16)</td><td rowspan="1" colspan="1">0.0591 (16)</td><td rowspan="1" colspan="1">0.0023 (11)</td><td rowspan="1" colspan="1">−0.0039 (11)</td><td rowspan="1" colspan="1">−0.0235 (13)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0455 (14)</td><td rowspan="1" colspan="1">0.0695 (16)</td><td rowspan="1" colspan="1">0.0521 (15)</td><td rowspan="1" colspan="1">−0.0036 (12)</td><td rowspan="1" colspan="1">−0.0103 (11)</td><td rowspan="1" colspan="1">−0.0226 (13)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.0535 (15)</td><td rowspan="1" colspan="1">0.0503 (13)</td><td rowspan="1" colspan="1">0.0554 (15)</td><td rowspan="1" colspan="1">−0.0023 (11)</td><td rowspan="1" colspan="1">0.0069 (12)</td><td rowspan="1" colspan="1">−0.0226 (12)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.093 (3)</td><td rowspan="1" colspan="1">0.124 (3)</td><td rowspan="1" colspan="1">0.082 (2)</td><td rowspan="1" colspan="1">0.017 (2)</td><td rowspan="1" colspan="1">−0.009 (2)</td><td rowspan="1" colspan="1">−0.068 (2)</td></tr><tr><td rowspan="1" colspan="1">C17</td><td rowspan="1" colspan="1">0.099 (3)</td><td rowspan="1" colspan="1">0.075 (2)</td><td rowspan="1" colspan="1">0.091 (3)</td><td rowspan="1" colspan="1">−0.0283 (19)</td><td rowspan="1" colspan="1">0.048 (2)</td><td rowspan="1" colspan="1">−0.0345 (19)</td></tr><tr><td rowspan="1" colspan="1">C18</td><td rowspan="1" colspan="1">0.077 (2)</td><td rowspan="1" colspan="1">0.0517 (16)</td><td rowspan="1" colspan="1">0.095 (3)</td><td rowspan="1" colspan="1">0.0024 (14)</td><td rowspan="1" colspan="1">0.0109 (19)</td><td rowspan="1" colspan="1">−0.0212 (16)</td></tr><tr><td rowspan="1" colspan="1">O3</td><td rowspan="1" colspan="1">0.0644 (14)</td><td rowspan="1" colspan="1">0.1174 (19)</td><td rowspan="1" colspan="1">0.0548 (12)</td><td rowspan="1" colspan="1">−0.0080 (13)</td><td rowspan="1" colspan="1">−0.0132 (10)</td><td rowspan="1" colspan="1">−0.0176 (12)</td></tr><tr><td rowspan="1" colspan="1">C19</td><td rowspan="1" colspan="1">0.104 (4)</td><td rowspan="1" colspan="1">0.311 (10)</td><td rowspan="1" colspan="1">0.079 (3)</td><td rowspan="1" colspan="1">−0.029 (5)</td><td rowspan="1" colspan="1">−0.018 (3)</td><td rowspan="1" colspan="1">−0.046 (5)</td></tr><tr><td rowspan="1" colspan="1">C20</td><td rowspan="1" colspan="1">0.096 (3)</td><td rowspan="1" colspan="1">0.195 (6)</td><td rowspan="1" colspan="1">0.079 (3)</td><td rowspan="1" colspan="1">−0.014 (3)</td><td rowspan="1" colspan="1">−0.029 (3)</td><td rowspan="1" colspan="1">−0.027 (3)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title><table-wrap position="anchor" id="d1e1779"><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">Br1—C3</td><td rowspan="1" colspan="1">1.880 (3)</td><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.376 (4)</td></tr><tr><td rowspan="1" colspan="1">Cl1—C5</td><td rowspan="1" colspan="1">1.733 (3)</td><td rowspan="1" colspan="1">C12—C15</td><td rowspan="1" colspan="1">1.532 (3)</td></tr><tr><td rowspan="1" colspan="1">O1—C2</td><td rowspan="1" colspan="1">1.338 (3)</td><td rowspan="1" colspan="1">C13—C14</td><td rowspan="1" colspan="1">1.385 (4)</td></tr><tr><td rowspan="1" colspan="1">O1—H1</td><td rowspan="1" colspan="1">0.8200</td><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">O2—C8</td><td rowspan="1" colspan="1">1.221 (3)</td><td rowspan="1" colspan="1">C14—H14</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N1—C7</td><td rowspan="1" colspan="1">1.285 (3)</td><td rowspan="1" colspan="1">C15—C17</td><td rowspan="1" colspan="1">1.516 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—N2</td><td rowspan="1" colspan="1">1.369 (3)</td><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.519 (5)</td></tr><tr><td rowspan="1" colspan="1">N2—C8</td><td rowspan="1" colspan="1">1.362 (3)</td><td rowspan="1" colspan="1">C15—C18</td><td rowspan="1" colspan="1">1.530 (4)</td></tr><tr><td rowspan="1" colspan="1">N2—H2</td><td rowspan="1" colspan="1">0.8601</td><td rowspan="1" colspan="1">C16—H16A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C1—C6</td><td rowspan="1" colspan="1">1.392 (4)</td><td rowspan="1" colspan="1">C16—H16B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.404 (4)</td><td rowspan="1" colspan="1">C16—H16C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C1—C7</td><td rowspan="1" colspan="1">1.457 (3)</td><td rowspan="1" colspan="1">C17—H17A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.402 (3)</td><td rowspan="1" colspan="1">C17—H17B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.371 (4)</td><td rowspan="1" colspan="1">C17—H17C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.378 (4)</td><td rowspan="1" colspan="1">C18—H18A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C18—H18B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.372 (4)</td><td rowspan="1" colspan="1">C18—H18C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C6—H6</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">O3—C20</td><td rowspan="1" colspan="1">1.369 (5)</td></tr><tr><td rowspan="1" colspan="1">C7—H7</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">O3—H3</td><td rowspan="1" colspan="1">0.8201</td></tr><tr><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.485 (3)</td><td rowspan="1" colspan="1">C19—C20</td><td rowspan="1" colspan="1">1.5362 (10)</td></tr><tr><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.379 (3)</td><td rowspan="1" colspan="1">C19—H19A</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C9—C14</td><td rowspan="1" colspan="1">1.385 (4)</td><td rowspan="1" colspan="1">C19—H19B</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.384 (3)</td><td rowspan="1" colspan="1">C19—H19C</td><td rowspan="1" colspan="1">0.9600</td></tr><tr><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C20—H20A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.381 (4)</td><td rowspan="1" colspan="1">C20—H20B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.9300</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—O1—H1</td><td rowspan="1" colspan="1">109.5</td><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">118.9</td></tr><tr><td rowspan="1" colspan="1">C7—N1—N2</td><td rowspan="1" colspan="1">118.4 (2)</td><td rowspan="1" colspan="1">C14—C13—H13</td><td rowspan="1" colspan="1">118.9</td></tr><tr><td rowspan="1" colspan="1">C8—N2—N1</td><td rowspan="1" colspan="1">116.5 (2)</td><td rowspan="1" colspan="1">C13—C14—C9</td><td rowspan="1" colspan="1">120.0 (2)</td></tr><tr><td rowspan="1" colspan="1">C8—N2—H2</td><td rowspan="1" colspan="1">121.8</td><td rowspan="1" colspan="1">C13—C14—H14</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">N1—N2—H2</td><td rowspan="1" colspan="1">121.8</td><td rowspan="1" colspan="1">C9—C14—H14</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2</td><td rowspan="1" colspan="1">119.7 (2)</td><td rowspan="1" colspan="1">C17—C15—C16</td><td rowspan="1" colspan="1">109.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C7</td><td rowspan="1" colspan="1">118.7 (3)</td><td rowspan="1" colspan="1">C17—C15—C18</td><td rowspan="1" colspan="1">108.2 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C7</td><td rowspan="1" colspan="1">121.5 (2)</td><td rowspan="1" colspan="1">C16—C15—C18</td><td rowspan="1" colspan="1">107.9 (3)</td></tr><tr><td rowspan="1" colspan="1">O1—C2—C3</td><td rowspan="1" colspan="1">118.6 (3)</td><td rowspan="1" colspan="1">C17—C15—C12</td><td rowspan="1" colspan="1">109.6 (2)</td></tr><tr><td rowspan="1" colspan="1">O1—C2—C1</td><td rowspan="1" colspan="1">123.5 (2)</td><td rowspan="1" colspan="1">C16—C15—C12</td><td rowspan="1" colspan="1">112.6 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">117.9 (2)</td><td rowspan="1" colspan="1">C18—C15—C12</td><td rowspan="1" colspan="1">108.6 (2)</td></tr><tr><td rowspan="1" colspan="1">C4—C3—C2</td><td rowspan="1" colspan="1">121.9 (3)</td><td rowspan="1" colspan="1">C15—C16—H16A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C4—C3—Br1</td><td rowspan="1" colspan="1">119.4 (2)</td><td rowspan="1" colspan="1">C15—C16—H16B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C2—C3—Br1</td><td rowspan="1" colspan="1">118.6 (2)</td><td rowspan="1" colspan="1">H16A—C16—H16B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5</td><td rowspan="1" colspan="1">119.1 (2)</td><td rowspan="1" colspan="1">C15—C16—H16C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C3—C4—H4</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">H16A—C16—H16C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">120.4</td><td rowspan="1" colspan="1">H16B—C16—H16C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—C5—C4</td><td rowspan="1" colspan="1">120.9 (3)</td><td rowspan="1" colspan="1">C15—C17—H17A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C6—C5—Cl1</td><td rowspan="1" colspan="1">120.5 (3)</td><td rowspan="1" colspan="1">C15—C17—H17B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C4—C5—Cl1</td><td rowspan="1" colspan="1">118.6 (2)</td><td rowspan="1" colspan="1">H17A—C17—H17B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C1</td><td rowspan="1" colspan="1">120.4 (3)</td><td rowspan="1" colspan="1">C15—C17—H17C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C5—C6—H6</td><td rowspan="1" colspan="1">119.8</td><td rowspan="1" colspan="1">H17A—C17—H17C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C1—C6—H6</td><td rowspan="1" colspan="1">119.8</td><td rowspan="1" colspan="1">H17B—C17—H17C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N1—C7—C1</td><td rowspan="1" colspan="1">118.3 (2)</td><td rowspan="1" colspan="1">C15—C18—H18A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N1—C7—H7</td><td rowspan="1" colspan="1">120.8</td><td rowspan="1" colspan="1">C15—C18—H18B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C1—C7—H7</td><td rowspan="1" colspan="1">120.8</td><td rowspan="1" colspan="1">H18A—C18—H18B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O2—C8—N2</td><td rowspan="1" colspan="1">121.4 (2)</td><td rowspan="1" colspan="1">C15—C18—H18C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">O2—C8—C9</td><td rowspan="1" colspan="1">122.2 (2)</td><td rowspan="1" colspan="1">H18A—C18—H18C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">N2—C8—C9</td><td rowspan="1" colspan="1">116.4 (2)</td><td rowspan="1" colspan="1">H18B—C18—H18C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C10—C9—C14</td><td rowspan="1" colspan="1">118.8 (2)</td><td rowspan="1" colspan="1">C20—O3—H3</td><td rowspan="1" colspan="1">109.6</td></tr><tr><td rowspan="1" colspan="1">C10—C9—C8</td><td rowspan="1" colspan="1">123.9 (2)</td><td rowspan="1" colspan="1">C20—C19—H19A</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C14—C9—C8</td><td rowspan="1" colspan="1">117.3 (2)</td><td rowspan="1" colspan="1">C20—C19—H19B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C9—C10—C11</td><td rowspan="1" colspan="1">119.9 (2)</td><td rowspan="1" colspan="1">H19A—C19—H19B</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">C20—C19—H19C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C11—C10—H10</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">H19A—C19—H19C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C11—C10</td><td rowspan="1" colspan="1">122.3 (2)</td><td rowspan="1" colspan="1">H19B—C19—H19C</td><td rowspan="1" colspan="1">109.5</td></tr><tr><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">118.9</td><td rowspan="1" colspan="1">O3—C20—C19</td><td rowspan="1" colspan="1">112.2 (4)</td></tr><tr><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">118.9</td><td rowspan="1" colspan="1">O3—C20—H20A</td><td rowspan="1" colspan="1">109.2</td></tr><tr><td rowspan="1" colspan="1">C13—C12—C11</td><td rowspan="1" colspan="1">116.8 (2)</td><td rowspan="1" colspan="1">C19—C20—H20A</td><td rowspan="1" colspan="1">109.2</td></tr><tr><td rowspan="1" colspan="1">C13—C12—C15</td><td rowspan="1" colspan="1">120.4 (2)</td><td rowspan="1" colspan="1">O3—C20—H20B</td><td rowspan="1" colspan="1">109.2</td></tr><tr><td rowspan="1" colspan="1">C11—C12—C15</td><td rowspan="1" colspan="1">122.8 (2)</td><td rowspan="1" colspan="1">C19—C20—H20B</td><td rowspan="1" colspan="1">109.2</td></tr><tr><td rowspan="1" colspan="1">C12—C13—C14</td><td rowspan="1" colspan="1">122.1 (2)</td><td rowspan="1" colspan="1">H20A—C20—H20B</td><td rowspan="1" colspan="1">107.9</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">C7—N1—N2—C8</td><td rowspan="1" colspan="1">177.0 (2)</td><td rowspan="1" colspan="1">N1—N2—C8—C9</td><td rowspan="1" colspan="1">−173.9 (2)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2—O1</td><td rowspan="1" colspan="1">179.8 (2)</td><td rowspan="1" colspan="1">O2—C8—C9—C10</td><td rowspan="1" colspan="1">157.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C7—C1—C2—O1</td><td rowspan="1" colspan="1">−1.4 (4)</td><td rowspan="1" colspan="1">N2—C8—C9—C10</td><td rowspan="1" colspan="1">−24.4 (4)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2—C3</td><td rowspan="1" colspan="1">0.0 (4)</td><td rowspan="1" colspan="1">O2—C8—C9—C14</td><td rowspan="1" colspan="1">−21.3 (4)</td></tr><tr><td rowspan="1" colspan="1">C7—C1—C2—C3</td><td rowspan="1" colspan="1">178.8 (2)</td><td rowspan="1" colspan="1">N2—C8—C9—C14</td><td rowspan="1" colspan="1">157.2 (2)</td></tr><tr><td rowspan="1" colspan="1">O1—C2—C3—C4</td><td rowspan="1" colspan="1">179.9 (2)</td><td rowspan="1" colspan="1">C14—C9—C10—C11</td><td rowspan="1" colspan="1">−0.7 (4)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">−0.3 (4)</td><td rowspan="1" colspan="1">C8—C9—C10—C11</td><td rowspan="1" colspan="1">−179.0 (2)</td></tr><tr><td rowspan="1" colspan="1">O1—C2—C3—Br1</td><td rowspan="1" colspan="1">−0.6 (3)</td><td rowspan="1" colspan="1">C9—C10—C11—C12</td><td rowspan="1" colspan="1">−0.8 (4)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—Br1</td><td rowspan="1" colspan="1">179.15 (19)</td><td rowspan="1" colspan="1">C10—C11—C12—C13</td><td rowspan="1" colspan="1">1.3 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">0.8 (4)</td><td rowspan="1" colspan="1">C10—C11—C12—C15</td><td rowspan="1" colspan="1">−178.6 (2)</td></tr><tr><td rowspan="1" colspan="1">Br1—C3—C4—C5</td><td rowspan="1" colspan="1">−178.6 (2)</td><td rowspan="1" colspan="1">C11—C12—C13—C14</td><td rowspan="1" colspan="1">−0.4 (4)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td><td rowspan="1" colspan="1">−1.0 (4)</td><td rowspan="1" colspan="1">C15—C12—C13—C14</td><td rowspan="1" colspan="1">179.5 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—Cl1</td><td rowspan="1" colspan="1">179.1 (2)</td><td rowspan="1" colspan="1">C12—C13—C14—C9</td><td rowspan="1" colspan="1">−1.1 (4)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—C1</td><td rowspan="1" colspan="1">0.8 (4)</td><td rowspan="1" colspan="1">C10—C9—C14—C13</td><td rowspan="1" colspan="1">1.6 (4)</td></tr><tr><td rowspan="1" colspan="1">Cl1—C5—C6—C1</td><td rowspan="1" colspan="1">−179.4 (2)</td><td rowspan="1" colspan="1">C8—C9—C14—C13</td><td rowspan="1" colspan="1">−180.0 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td><td rowspan="1" colspan="1">−0.3 (4)</td><td rowspan="1" colspan="1">C13—C12—C15—C17</td><td rowspan="1" colspan="1">−53.7 (4)</td></tr><tr><td rowspan="1" colspan="1">C7—C1—C6—C5</td><td rowspan="1" colspan="1">−179.1 (2)</td><td rowspan="1" colspan="1">C11—C12—C15—C17</td><td rowspan="1" colspan="1">126.2 (3)</td></tr><tr><td rowspan="1" colspan="1">N2—N1—C7—C1</td><td rowspan="1" colspan="1">−176.7 (2)</td><td rowspan="1" colspan="1">C13—C12—C15—C16</td><td rowspan="1" colspan="1">−176.2 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C7—N1</td><td rowspan="1" colspan="1">−178.0 (2)</td><td rowspan="1" colspan="1">C11—C12—C15—C16</td><td rowspan="1" colspan="1">3.7 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C7—N1</td><td rowspan="1" colspan="1">3.2 (4)</td><td rowspan="1" colspan="1">C13—C12—C15—C18</td><td rowspan="1" colspan="1">64.3 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—N2—C8—O2</td><td rowspan="1" colspan="1">4.6 (4)</td><td rowspan="1" colspan="1">C11—C12—C15—C18</td><td rowspan="1" colspan="1">−115.8 (3)</td></tr></table></table-wrap></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, °)</title><table-wrap position="anchor" id="d1e2659"><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">O1—H1···N1</td><td rowspan="1" colspan="1">0.82</td><td rowspan="1" colspan="1">1.86</td><td rowspan="1" colspan="1">2.577 (3)</td><td rowspan="1" colspan="1">145</td></tr><tr><td rowspan="1" colspan="1">N2—H2···O3</td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">2.10</td><td rowspan="1" colspan="1">2.865 (3)</td><td rowspan="1" colspan="1">147</td></tr><tr><td rowspan="1" colspan="1">O3—H3···O2<sup>i</sup></td><td rowspan="1" colspan="1">0.82</td><td rowspan="1" colspan="1">1.94</td><td rowspan="1" colspan="1">2.755 (3)</td><td rowspan="1" colspan="1">171</td></tr><tr><td rowspan="1" colspan="1">C14—H14···O2<sup>ii</sup></td><td rowspan="1" colspan="1">0.93</td><td rowspan="1" colspan="1">2.54</td><td rowspan="1" colspan="1">3.418 (3)</td><td rowspan="1" colspan="1">157</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+2, −<italic>y</italic>+1, −<italic>z</italic>+1; (ii) −<italic>x</italic>+3, −<italic>y</italic>+1, −<italic>z</italic>+1.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Bruker (2004). <italic>APEX2</italic> and <italic>SAINT</italic> Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). <italic>Eur. J. Med. Chem.</italic>
<bold>35</bold>, 805–813.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). <italic>Acta Cryst.</italic> E<bold>64</bold>, o1594–o1595.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). <italic>Bioorg. Med. Chem.</italic>
<bold>14</bold>, 7482–7489.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Prabhakaran, R., Huang, R. & Natarajan, K. (2006). <italic>Inorg. Chim. Acta</italic>, <bold>359</bold>, 3359–3362.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Sheldrick, G. M. (1996). <italic>SADABS</italic>, University of Göttingen, Germany.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Shivakumar, K., Shashidhar, T., Reddy, P. V. & Halli, M. B. (2008). <italic>J. Coord. Chem.</italic>
<bold>61</bold>, 2274–2287.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Spek, A. L. (2009). <italic>Acta Cryst.</italic> D<bold>65</bold>, 148–155.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Thirugnanasundar, A., Suresh, J., Ramu, A. & RajaGopal, G. (2011). <italic>Acta Cryst.</italic> E<bold>67</bold>, o2303.</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">O1—H1⋯N1</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.82</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.86</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.577 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">145</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N2—H2⋯O3</td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.86</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.10</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.865 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">147</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O3—H3⋯O2<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.82</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.94</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.755 (3)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">171</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C14—H14⋯O2<sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.93</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.54</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.418 (3)</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-67-o2857-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-67-o2857-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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