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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Cyclohexanaminium trichloroacetate</title><author><name sortKey="Shahwar, Durre" sort="Shahwar, Durre" uniqKey="Shahwar D" first="Durre" last="Shahwar">Durre Shahwar</name><affiliation><nlm:aff id="a">Department of Chemistry, Government College University, Lahore,<country>Pakistan</country></nlm:aff></affiliation></author><author><name sortKey="Tahir, M Nawaz" sort="Tahir, M Nawaz" uniqKey="Tahir M" first="M. Nawaz" last="Tahir">M. Nawaz Tahir</name><affiliation><nlm:aff id="b">Department of Physics, University of Sargodha, Sargodha,<country>Pakistan</country></nlm:aff></affiliation></author><author><name sortKey="Ahmad, Naeem" sort="Ahmad, Naeem" uniqKey="Ahmad N" first="Naeem" last="Ahmad">Naeem Ahmad</name><affiliation><nlm:aff id="a">Department of Chemistry, Government College University, Lahore,<country>Pakistan</country></nlm:aff></affiliation></author><author><name sortKey="Khan, Muhammad Akmal" sort="Khan, Muhammad Akmal" uniqKey="Khan M" first="Muhammad Akmal" last="Khan">Muhammad Akmal Khan</name><affiliation><nlm:aff id="a">Department of Chemistry, Government College University, Lahore,<country>Pakistan</country></nlm:aff></affiliation></author><author><name sortKey="Saeed, Afifa" sort="Saeed, Afifa" uniqKey="Saeed A" first="Afifa" last="Saeed">Afifa Saeed</name><affiliation><nlm:aff id="a">Department of Chemistry, Government College University, Lahore,<country>Pakistan</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">21583170</idno><idno type="pmc">2969657</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969657</idno><idno type="RBID">PMC:2969657</idno><idno type="doi">10.1107/S1600536809017504</idno><date when="2009">2009</date><idno type="wicri:Area/Pmc/Corpus">000A13</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A13</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Cyclohexanaminium trichloroacetate</title><author><name sortKey="Shahwar, Durre" sort="Shahwar, Durre" uniqKey="Shahwar D" first="Durre" last="Shahwar">Durre Shahwar</name><affiliation><nlm:aff id="a">Department of Chemistry, Government College University, Lahore,<country>Pakistan</country></nlm:aff></affiliation></author><author><name sortKey="Tahir, M Nawaz" sort="Tahir, M Nawaz" uniqKey="Tahir M" first="M. Nawaz" last="Tahir">M. Nawaz Tahir</name><affiliation><nlm:aff id="b">Department of Physics, University of Sargodha, Sargodha,<country>Pakistan</country></nlm:aff></affiliation></author><author><name sortKey="Ahmad, Naeem" sort="Ahmad, Naeem" uniqKey="Ahmad N" first="Naeem" last="Ahmad">Naeem Ahmad</name><affiliation><nlm:aff id="a">Department of Chemistry, Government College University, Lahore,<country>Pakistan</country></nlm:aff></affiliation></author><author><name sortKey="Khan, Muhammad Akmal" sort="Khan, Muhammad Akmal" uniqKey="Khan M" first="Muhammad Akmal" last="Khan">Muhammad Akmal Khan</name><affiliation><nlm:aff id="a">Department of Chemistry, Government College University, Lahore,<country>Pakistan</country></nlm:aff></affiliation></author><author><name sortKey="Saeed, Afifa" sort="Saeed, Afifa" uniqKey="Saeed A" first="Afifa" last="Saeed">Afifa Saeed</name><affiliation><nlm:aff id="a">Department of Chemistry, Government College University, Lahore,<country>Pakistan</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="2009">2009</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>In the crystal of the title compound, C<sub>6</sub>H<sub>14</sub>N<sup>+</sup>·C<sub>2</sub>Cl<sub>3</sub>O<sub>2</sub><sup>−</sup>, centrosymmetric assemblies of two cyclohexanaminium cations and two trichloroacetate ions are linked by N—H⋯O hydrogen bonds, thereby forming <italic>R</italic><sub>4</sub><sup>4</sup>(12) ring motifs. Further N—H⋯O interactions link the tetramers into chains propagating along the <italic>a</italic> axis.</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></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">21583170</article-id><article-id pub-id-type="pmc">2969657</article-id><article-id pub-id-type="publisher-id">hb2970</article-id><article-id pub-id-type="doi">10.1107/S1600536809017504</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536809017504</article-id><article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject></subj-group></article-categories><title-group><article-title>Cyclohexanaminium trichloroacetate</article-title><alt-title><italic>C<sub>6</sub>H<sub>14</sub>N<sup>+</sup>·C<sub>2</sub>Cl<sub>3</sub>O<sub>2</sub><sup>−</sup></italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Shahwar</surname><given-names>Durre</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Tahir</surname><given-names>M. Nawaz</given-names></name><xref ref-type="aff" rid="b">b</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><contrib contrib-type="author"><name><surname>Ahmad</surname><given-names>Naeem</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Khan</surname><given-names>Muhammad Akmal</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Saeed</surname><given-names>Afifa</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><aff id="a"><label>a</label>Department of Chemistry, Government College University, Lahore,<country>Pakistan</country></aff><aff id="b"><label>b</label>Department of Physics, University of Sargodha, Sargodha,<country>Pakistan</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>dmntahir_uos@yahoo.com</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>6</month><year>2009</year></pub-date><pub-date pub-type="epub"><day>20</day><month>5</month><year>2009</year></pub-date><pub-date pub-type="pmc-release"><day>20</day><month>5</month><year>2009</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>65</volume><issue>Pt 6</issue><issue-id pub-id-type="publisher-id">e090600</issue-id><fpage>o1313</fpage><lpage>o1313</lpage><history><date date-type="received"><day>09</day><month>5</month><year>2009</year></date><date date-type="accepted"><day>10</day><month>5</month><year>2009</year></date></history><permissions><copyright-statement>© Shahwar et al. 2009</copyright-statement><copyright-year>2009</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/S1600536809017504">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>In the crystal of the title compound, C<sub>6</sub>H<sub>14</sub>N<sup>+</sup>·C<sub>2</sub>Cl<sub>3</sub>O<sub>2</sub><sup>−</sup>, centrosymmetric assemblies of two cyclohexanaminium cations and two trichloroacetate ions are linked by N—H⋯O hydrogen bonds, thereby forming <italic>R</italic><sub>4</sub><sup>4</sup>(12) ring motifs. Further N—H⋯O interactions link the tetramers into chains propagating along the <italic>a</italic> axis.</p></abstract></article-meta></front><body><sec id="sec1"><title>Related literature</title><p>For related structures, see: Shahwar <italic>et al.</italic> (2009<xref ref-type="bibr" rid="bb8"> ▶</xref>); Wang <italic>et al.</italic> (2005<xref ref-type="bibr" rid="bb11"> ▶</xref>); Jones & Ahrens (1998<xref ref-type="bibr" rid="bb7"> ▶</xref>). For reference structural data, see: Allen <italic>et al.</italic> (1987<xref ref-type="bibr" rid="bb1"> ▶</xref>). For graph-set notation, see: Bernstein <italic>et al.</italic> (1995<xref ref-type="bibr" rid="bb2"> ▶</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-65-o1313-scheme1.jpg" position="float"></graphic></chem-struct></p></sec><sec sec-type="" 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>6</sub>H<sub>14</sub>N<sup>+</sup>·C<sub>2</sub>Cl<sub>3</sub>O<sub>2</sub><sup>−</sup></p></list-item><list-item><p><italic>M</italic><italic><sub>r</sub></italic> = 262.55</p></list-item><list-item><p>Monoclinic, <inline-formula><inline-graphic xlink:href="e-65-o1313-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></p></list-item><list-item><p><italic>a</italic> = 6.7217 (4) Å</p></list-item><list-item><p><italic>b</italic> = 21.2482 (15) Å</p></list-item><list-item><p><italic>c</italic> = 10.6908 (6) Å</p></list-item><list-item><p>β = 126.590 (3)°</p></list-item><list-item><p><italic>V</italic> = 1225.98 (14) Å<sup>3</sup></p></list-item><list-item><p><italic>Z</italic> = 4</p></list-item><list-item><p>Mo <italic>K</italic>α radiation</p></list-item><list-item><p>μ = 0.72 mm<sup>−1</sup></p></list-item><list-item><p><italic>T</italic> = 296 K</p></list-item><list-item><p>0.25 × 0.18 × 0.12 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 CCD diffractometer</p></list-item><list-item><p>Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2005<xref ref-type="bibr" rid="bb3"> ▶</xref>) <italic>T</italic><sub>min</sub> = 0.853, <italic>T</italic><sub>max</sub> = 0.919</p></list-item><list-item><p>13379 measured reflections</p></list-item><list-item><p>2910 independent reflections</p></list-item><list-item><p>1710 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</p></list-item><list-item><p><italic>R</italic><sub>int</sub> = 0.038</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>)] = 0.066</p></list-item><list-item><p><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.215</p></list-item><list-item><p><italic>S</italic> = 1.05</p></list-item><list-item><p>2910 reflections</p></list-item><list-item><p>139 parameters</p></list-item><list-item><p>H atoms treated by a mixture of independent and constrained refinement</p></list-item><list-item><p>Δρ<sub>max</sub> = 0.73 e Å<sup>−3</sup></p></list-item><list-item><p>Δρ<sub>min</sub> = −0.37 e Å<sup>−3</sup></p></list-item></list></p></sec></sec><sec id="d5e500"><title></title><p>Data collection: <italic>APEX2</italic> (Bruker, 2007<xref ref-type="bibr" rid="bb4"> ▶</xref>); cell refinement: <italic>SAINT</italic> (Bruker, 2007<xref ref-type="bibr" rid="bb4"> ▶</xref>); data reduction: <italic>SAINT</italic>; program(s) used to solve structure: <italic>SHELXS97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb9"> ▶</xref>); program(s) used to refine structure: <italic>SHELXL97</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb9"> ▶</xref>); molecular graphics: <italic>ORTEP-3 for Windows</italic> (Farrugia, 1997<xref ref-type="bibr" rid="bb5"> ▶</xref>) and <italic>PLATON</italic> (Spek, 2009<xref ref-type="bibr" rid="bb10"> ▶</xref>); software used to prepare material for publication: <italic>WinGX</italic> (Farrugia, 1999<xref ref-type="bibr" rid="bb6"> ▶</xref>) and <italic>PLATON</italic>.</p></sec></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data" xlink:href="e-65-o1313-sup1.cif" position="float" xlink:type="simple"><p>Crystal structure: contains datablocks global, I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536809017504/hb2970sup1.cif">10.1107/S1600536809017504/hb2970sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-65-o1313-sup1.cif" position="float" xlink:type="simple"></media></supplementary-material><supplementary-material content-type="local-data" xlink:href="e-65-o1313-Isup2.hkl" position="float" xlink:type="simple"><p>Structure factors: contains datablocks I. DOI: <ext-link ext-link-type="uri" xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536809017504/hb2970Isup2.hkl">10.1107/S1600536809017504/hb2970Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-65-o1313-Isup2.hkl" position="float" xlink:type="simple"></media></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?hb2970&file=hb2970sup0.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?hb2970sup1&Qmime=cif" xlink:type="simple">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?hb2970&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?hb2970">HB2970</ext-link>).</p></fn></fn-group><ack><p>NA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN 042–120599-PS2–156).</p></ack><app-group><app><title>supplementary crystallographic
information</title><sec id="comment"><title>Comment </title><p>In continuation of synthesizing various organic ammonium salts (Shahwar <italic>et
al.</italic>, 2009), the title compound (I), (Fig. 1) is being reported.
The crystal structures of (II) Cyclohexylammonium dichloroacetate (Wang <italic>et
al.</italic>, 2005) and (III) Cyclohexylamine cyclohexylammonium chloride
(Jones &
Ahrens, 1998) have been reported.</p><p>In (I), the bond distance and bond angles
are within normal ranges (Allen <italic>et al.</italic>, 1987). In the title
compound,
two cyclohexanaminium ions and two trichloroacetate ions are interlinked
through intermolecular H-bonding of N—H···O type (Table 1) forming ring
motifs <italic>R</italic><sub>4</sub><sup>4</sup>(12) (Bernstein <italic>et al.</italic>, 1995) (Fig. 2).
The ring motifs are
further connected through the same along the <italic>a</italic> axis resulting in
one-dimensional polymeric chains. The cyclohexanaminium ions are in chair
confirmations with N-atoms at a distance of 0.628 (9)Å from the central
plane.</p></sec><sec id="experimental"><title>Experimental </title><p>A solution of trichloroacetic acid (1.635 g, 0.01 mol) in 20 ml of
dichloromethane was prepared. To this solution cyclohexyl amine (1.14 ml, 0.01 mol) was added dropwise and stirred for 30 min. The precipitate were filtered
out and recrystallized in hot chloroform to yield colourless rods of (I).</p></sec><sec id="refinement"><title>Refinement </title><p>The coordinates of H-atoms attached to N1 and C1 were refined.
The other H atoms were positioned geometrically (C—H = 0.97 Å)
and refined as riding. The constraint U<sub>iso</sub>(H) =
1.2U<sub>eq</sub>(carrier) was applied for all H atoms.</p></sec><sec id="figures"><title>Figures</title><fig id="Fap1"><label>Fig. 1.</label><caption><p>View of (I) with displacement ellipsoids drawn at the 30% probability level. H-atoms are shown by small spheres of arbitrary radius.</p></caption><graphic xlink:href="e-65-o1313-fig1"></graphic></fig><fig id="Fap2"><label>Fig. 2.</label><caption><p>The partial packing in (I) showing intermolecular H-bonding between NH3 and trichloroacetate ions and the resulting ring motif.</p></caption><graphic xlink:href="e-65-o1313-fig2"></graphic></fig></sec><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e128"><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>6</sub>H<sub>14</sub>N<sup>+</sup>·C<sub>2</sub>Cl<sub>3</sub>O<sub>2</sub><sup>−</sup></td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 544</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 262.55</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 1.422 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 2910 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 6.7217 (4) Å</td><td rowspan="1" colspan="1">θ = 2.6–27.9°</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 21.2482 (15) Å</td><td rowspan="1" colspan="1">µ = 0.72 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 10.6908 (6) Å</td><td rowspan="1" colspan="1"><italic>T</italic> = 296 K</td></tr><tr><td rowspan="1" colspan="1">β = 126.590 (3)°</td><td rowspan="1" colspan="1">Rod, colorless</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1225.98 (14) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.25 × 0.18 × 0.12 mm</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 4</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e268"><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 CCD diffractometer</td><td rowspan="1" colspan="1">2910 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">1710 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> = 0.038</td></tr><tr><td rowspan="1" colspan="1">Detector resolution: 7.50 pixels mm<sup>-1</sup></td><td rowspan="1" colspan="1">θ<sub>max</sub> = 27.9°, θ<sub>min</sub> = 2.6°</td></tr><tr><td rowspan="1" colspan="1">ω scans</td><td rowspan="1" colspan="1"><italic>h</italic> = −8→8</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (<italic>SADABS</italic>; Bruker, 2005)</td><td rowspan="1" colspan="1"><italic>k</italic> = −27→26</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.853, <italic>T</italic><sub>max</sub> = 0.919</td><td rowspan="1" colspan="1"><italic>l</italic> = −12→14</td></tr><tr><td rowspan="1" colspan="1">13379 measured reflections</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e388"><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>)] = 0.066</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>) = 0.215</td><td rowspan="1" colspan="1">H atoms treated by a mixture of independent and constrained refinement</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.05</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.1089<italic>P</italic>)<sup>2</sup> + 0.5776<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">2910 reflections</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1">139 parameters</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.73 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> = −0.37 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="d1e545"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. Bond distances, angles <italic>etc</italic>. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles</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="d1e647"><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">N1</td><td rowspan="1" colspan="1">0.2904 (5)</td><td rowspan="1" colspan="1">0.05714 (15)</td><td rowspan="1" colspan="1">0.0547 (4)</td><td rowspan="1" colspan="1">0.0480 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.4574 (6)</td><td rowspan="1" colspan="1">0.08854 (16)</td><td rowspan="1" colspan="1">0.2093 (4)</td><td rowspan="1" colspan="1">0.0463 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.7215 (6)</td><td rowspan="1" colspan="1">0.06696 (19)</td><td rowspan="1" colspan="1">0.2878 (5)</td><td rowspan="1" colspan="1">0.0568 (11)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.8922 (7)</td><td rowspan="1" colspan="1">0.0967 (2)</td><td rowspan="1" colspan="1">0.4465 (5)</td><td rowspan="1" colspan="1">0.0731 (15)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.8100 (8)</td><td rowspan="1" colspan="1">0.0827 (3)</td><td rowspan="1" colspan="1">0.5472 (6)</td><td rowspan="1" colspan="1">0.0816 (18)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.5457 (8)</td><td rowspan="1" colspan="1">0.1032 (2)</td><td rowspan="1" colspan="1">0.4704 (5)</td><td rowspan="1" colspan="1">0.0764 (17)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.3726 (7)</td><td rowspan="1" colspan="1">0.0733 (2)</td><td rowspan="1" colspan="1">0.3100 (5)</td><td rowspan="1" colspan="1">0.0626 (15)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Cl1</td><td rowspan="1" colspan="1">0.9294 (2)</td><td rowspan="1" colspan="1">0.30601 (6)</td><td rowspan="1" colspan="1">0.38465 (15)</td><td rowspan="1" colspan="1">0.0791 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Cl2</td><td rowspan="1" colspan="1">0.7598 (3)</td><td rowspan="1" colspan="1">0.28803 (6)</td><td rowspan="1" colspan="1">0.57059 (16)</td><td rowspan="1" colspan="1">0.1029 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Cl3</td><td rowspan="1" colspan="1">0.4167 (2)</td><td rowspan="1" colspan="1">0.28226 (6)</td><td rowspan="1" colspan="1">0.23280 (17)</td><td rowspan="1" colspan="1">0.0950 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.7893 (5)</td><td rowspan="1" colspan="1">0.42783 (12)</td><td rowspan="1" colspan="1">0.4227 (4)</td><td rowspan="1" colspan="1">0.0711 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.4297 (5)</td><td rowspan="1" colspan="1">0.40429 (14)</td><td rowspan="1" colspan="1">0.3696 (3)</td><td rowspan="1" colspan="1">0.0680 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.6272 (5)</td><td rowspan="1" colspan="1">0.39152 (15)</td><td rowspan="1" colspan="1">0.3948 (3)</td><td rowspan="1" colspan="1">0.0406 (9)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.6778 (7)</td><td rowspan="1" colspan="1">0.32022 (15)</td><td rowspan="1" colspan="1">0.3937 (4)</td><td rowspan="1" colspan="1">0.0488 (10)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">0.432 (7)</td><td rowspan="1" colspan="1">0.1331 (19)</td><td rowspan="1" colspan="1">0.186 (4)</td><td rowspan="1" colspan="1">0.0553*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1A</td><td rowspan="1" colspan="1">0.141 (8)</td><td rowspan="1" colspan="1">0.0678 (19)</td><td rowspan="1" colspan="1">0.011 (5)</td><td rowspan="1" colspan="1">0.0575*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1B</td><td rowspan="1" colspan="1">0.333 (7)</td><td rowspan="1" colspan="1">0.0632 (19)</td><td rowspan="1" colspan="1">−0.002 (5)</td><td rowspan="1" colspan="1">0.0575*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1C</td><td rowspan="1" colspan="1">0.285 (7)</td><td rowspan="1" colspan="1">0.010 (2)</td><td rowspan="1" colspan="1">0.071 (4)</td><td rowspan="1" colspan="1">0.0575*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2A</td><td rowspan="1" colspan="1">0.72989</td><td rowspan="1" colspan="1">0.02151</td><td rowspan="1" colspan="1">0.29833</td><td rowspan="1" colspan="1">0.0680*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H2B</td><td rowspan="1" colspan="1">0.77440</td><td rowspan="1" colspan="1">0.07841</td><td rowspan="1" colspan="1">0.22401</td><td rowspan="1" colspan="1">0.0680*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3A</td><td rowspan="1" colspan="1">1.05899</td><td rowspan="1" colspan="1">0.08085</td><td rowspan="1" colspan="1">0.49682</td><td rowspan="1" colspan="1">0.0877*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3B</td><td rowspan="1" colspan="1">0.89524</td><td rowspan="1" colspan="1">0.14188</td><td rowspan="1" colspan="1">0.43499</td><td rowspan="1" colspan="1">0.0877*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4A</td><td rowspan="1" colspan="1">0.91813</td><td rowspan="1" colspan="1">0.10433</td><td rowspan="1" colspan="1">0.64607</td><td rowspan="1" colspan="1">0.0973*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4B</td><td rowspan="1" colspan="1">0.82413</td><td rowspan="1" colspan="1">0.03787</td><td rowspan="1" colspan="1">0.56795</td><td rowspan="1" colspan="1">0.0973*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5A</td><td rowspan="1" colspan="1">0.53487</td><td rowspan="1" colspan="1">0.14865</td><td rowspan="1" colspan="1">0.46040</td><td rowspan="1" colspan="1">0.0919*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5B</td><td rowspan="1" colspan="1">0.49516</td><td rowspan="1" colspan="1">0.09095</td><td rowspan="1" colspan="1">0.53505</td><td rowspan="1" colspan="1">0.0919*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6A</td><td rowspan="1" colspan="1">0.20568</td><td rowspan="1" colspan="1">0.08903</td><td rowspan="1" colspan="1">0.25991</td><td rowspan="1" colspan="1">0.0753*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6B</td><td rowspan="1" colspan="1">0.37023</td><td rowspan="1" colspan="1">0.02808</td><td rowspan="1" colspan="1">0.32080</td><td rowspan="1" colspan="1">0.0753*</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="d1e1023"><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">N1</td><td rowspan="1" colspan="1">0.0401 (14)</td><td rowspan="1" colspan="1">0.0439 (17)</td><td rowspan="1" colspan="1">0.0601 (19)</td><td rowspan="1" colspan="1">0.0011 (12)</td><td rowspan="1" colspan="1">0.0300 (14)</td><td rowspan="1" colspan="1">0.0040 (13)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0436 (16)</td><td rowspan="1" colspan="1">0.0341 (17)</td><td rowspan="1" colspan="1">0.057 (2)</td><td rowspan="1" colspan="1">0.0007 (13)</td><td rowspan="1" colspan="1">0.0278 (16)</td><td rowspan="1" colspan="1">0.0035 (14)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0426 (17)</td><td rowspan="1" colspan="1">0.063 (2)</td><td rowspan="1" colspan="1">0.066 (2)</td><td rowspan="1" colspan="1">0.0015 (16)</td><td rowspan="1" colspan="1">0.0331 (17)</td><td rowspan="1" colspan="1">0.0043 (18)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0463 (19)</td><td rowspan="1" colspan="1">0.084 (3)</td><td rowspan="1" colspan="1">0.072 (3)</td><td rowspan="1" colspan="1">−0.0074 (19)</td><td rowspan="1" colspan="1">0.026 (2)</td><td rowspan="1" colspan="1">−0.002 (2)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.066 (2)</td><td rowspan="1" colspan="1">0.093 (4)</td><td rowspan="1" colspan="1">0.064 (3)</td><td rowspan="1" colspan="1">−0.002 (2)</td><td rowspan="1" colspan="1">0.027 (2)</td><td rowspan="1" colspan="1">−0.007 (2)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.079 (3)</td><td rowspan="1" colspan="1">0.088 (3)</td><td rowspan="1" colspan="1">0.068 (3)</td><td rowspan="1" colspan="1">0.003 (2)</td><td rowspan="1" colspan="1">0.047 (2)</td><td rowspan="1" colspan="1">−0.010 (2)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0508 (19)</td><td rowspan="1" colspan="1">0.072 (3)</td><td rowspan="1" colspan="1">0.074 (3)</td><td rowspan="1" colspan="1">−0.0019 (18)</td><td rowspan="1" colspan="1">0.042 (2)</td><td rowspan="1" colspan="1">−0.001 (2)</td></tr><tr><td rowspan="1" colspan="1">Cl1</td><td rowspan="1" colspan="1">0.0779 (7)</td><td rowspan="1" colspan="1">0.0700 (7)</td><td rowspan="1" colspan="1">0.0894 (8)</td><td rowspan="1" colspan="1">0.0142 (5)</td><td rowspan="1" colspan="1">0.0499 (7)</td><td rowspan="1" colspan="1">−0.0143 (6)</td></tr><tr><td rowspan="1" colspan="1">Cl2</td><td rowspan="1" colspan="1">0.1635 (14)</td><td rowspan="1" colspan="1">0.0733 (8)</td><td rowspan="1" colspan="1">0.0817 (9)</td><td rowspan="1" colspan="1">0.0174 (8)</td><td rowspan="1" colspan="1">0.0784 (10)</td><td rowspan="1" colspan="1">0.0311 (6)</td></tr><tr><td rowspan="1" colspan="1">Cl3</td><td rowspan="1" colspan="1">0.0748 (7)</td><td rowspan="1" colspan="1">0.0673 (8)</td><td rowspan="1" colspan="1">0.0937 (9)</td><td rowspan="1" colspan="1">−0.0196 (5)</td><td rowspan="1" colspan="1">0.0236 (7)</td><td rowspan="1" colspan="1">−0.0294 (6)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0498 (14)</td><td rowspan="1" colspan="1">0.0401 (14)</td><td rowspan="1" colspan="1">0.111 (2)</td><td rowspan="1" colspan="1">−0.0005 (11)</td><td rowspan="1" colspan="1">0.0413 (15)</td><td rowspan="1" colspan="1">0.0006 (14)</td></tr><tr><td rowspan="1" colspan="1">O2</td><td rowspan="1" colspan="1">0.0564 (15)</td><td rowspan="1" colspan="1">0.0762 (19)</td><td rowspan="1" colspan="1">0.0787 (19)</td><td rowspan="1" colspan="1">0.0110 (13)</td><td rowspan="1" colspan="1">0.0442 (15)</td><td rowspan="1" colspan="1">0.0000 (14)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0409 (16)</td><td rowspan="1" colspan="1">0.0400 (17)</td><td rowspan="1" colspan="1">0.0342 (15)</td><td rowspan="1" colspan="1">0.0016 (13)</td><td rowspan="1" colspan="1">0.0187 (13)</td><td rowspan="1" colspan="1">0.0004 (12)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0579 (19)</td><td rowspan="1" colspan="1">0.0354 (17)</td><td rowspan="1" colspan="1">0.0418 (17)</td><td rowspan="1" colspan="1">−0.0009 (14)</td><td rowspan="1" colspan="1">0.0236 (16)</td><td rowspan="1" colspan="1">0.0005 (13)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, °)</title><table-wrap position="anchor" id="d1e1303"><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">Cl1—C8</td><td rowspan="1" colspan="1">1.776 (6)</td><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.523 (6)</td></tr><tr><td rowspan="1" colspan="1">Cl2—C8</td><td rowspan="1" colspan="1">1.762 (4)</td><td rowspan="1" colspan="1">C1—H1</td><td rowspan="1" colspan="1">0.97 (4)</td></tr><tr><td rowspan="1" colspan="1">Cl3—C8</td><td rowspan="1" colspan="1">1.758 (4)</td><td rowspan="1" colspan="1">C2—H2B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">O1—C7</td><td rowspan="1" colspan="1">1.218 (5)</td><td rowspan="1" colspan="1">C2—H2A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">O2—C7</td><td rowspan="1" colspan="1">1.217 (5)</td><td rowspan="1" colspan="1">C3—H3A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">N1—C1</td><td rowspan="1" colspan="1">1.492 (5)</td><td rowspan="1" colspan="1">C3—H3B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">N1—H1A</td><td rowspan="1" colspan="1">0.85 (6)</td><td rowspan="1" colspan="1">C4—H4A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">N1—H1C</td><td rowspan="1" colspan="1">1.02 (4)</td><td rowspan="1" colspan="1">C4—H4B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">N1—H1B</td><td rowspan="1" colspan="1">0.82 (5)</td><td rowspan="1" colspan="1">C5—H5B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C1—C6</td><td rowspan="1" colspan="1">1.523 (7)</td><td rowspan="1" colspan="1">C5—H5A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.513 (7)</td><td rowspan="1" colspan="1">C6—H6B</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.508 (6)</td><td rowspan="1" colspan="1">C6—H6A</td><td rowspan="1" colspan="1">0.9700</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.504 (8)</td><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.554 (5)</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.510 (9)</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">C1—N1—H1C</td><td rowspan="1" colspan="1">109 (2)</td><td rowspan="1" colspan="1">H3A—C3—H3B</td><td rowspan="1" colspan="1">108.00</td></tr><tr><td rowspan="1" colspan="1">C1—N1—H1A</td><td rowspan="1" colspan="1">111 (3)</td><td rowspan="1" colspan="1">C3—C4—H4A</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">C1—N1—H1B</td><td rowspan="1" colspan="1">113 (3)</td><td rowspan="1" colspan="1">C3—C4—H4B</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">H1B—N1—H1C</td><td rowspan="1" colspan="1">110 (4)</td><td rowspan="1" colspan="1">C5—C4—H4A</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">H1A—N1—H1B</td><td rowspan="1" colspan="1">112 (5)</td><td rowspan="1" colspan="1">C5—C4—H4B</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">H1A—N1—H1C</td><td rowspan="1" colspan="1">102 (4)</td><td rowspan="1" colspan="1">H4A—C4—H4B</td><td rowspan="1" colspan="1">108.00</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2</td><td rowspan="1" colspan="1">109.8 (3)</td><td rowspan="1" colspan="1">C4—C5—H5A</td><td rowspan="1" colspan="1">110.00</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C6</td><td rowspan="1" colspan="1">109.7 (4)</td><td rowspan="1" colspan="1">C4—C5—H5B</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6</td><td rowspan="1" colspan="1">110.7 (3)</td><td rowspan="1" colspan="1">C6—C5—H5A</td><td rowspan="1" colspan="1">110.00</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3</td><td rowspan="1" colspan="1">110.6 (4)</td><td rowspan="1" colspan="1">C6—C5—H5B</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4</td><td rowspan="1" colspan="1">111.4 (4)</td><td rowspan="1" colspan="1">H5A—C5—H5B</td><td rowspan="1" colspan="1">108.00</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5</td><td rowspan="1" colspan="1">111.6 (4)</td><td rowspan="1" colspan="1">C1—C6—H6A</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6</td><td rowspan="1" colspan="1">110.7 (4)</td><td rowspan="1" colspan="1">C1—C6—H6B</td><td rowspan="1" colspan="1">110.00</td></tr><tr><td rowspan="1" colspan="1">C1—C6—C5</td><td rowspan="1" colspan="1">110.5 (4)</td><td rowspan="1" colspan="1">C5—C6—H6A</td><td rowspan="1" colspan="1">109.00</td></tr><tr><td rowspan="1" colspan="1">N1—C1—H1</td><td rowspan="1" colspan="1">105 (2)</td><td rowspan="1" colspan="1">C5—C6—H6B</td><td rowspan="1" colspan="1">110.00</td></tr><tr><td rowspan="1" colspan="1">C2—C1—H1</td><td rowspan="1" colspan="1">114 (3)</td><td rowspan="1" colspan="1">H6A—C6—H6B</td><td rowspan="1" colspan="1">108.00</td></tr><tr><td rowspan="1" colspan="1">C6—C1—H1</td><td rowspan="1" colspan="1">108 (3)</td><td rowspan="1" colspan="1">O1—C7—O2</td><td rowspan="1" colspan="1">127.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2A</td><td rowspan="1" colspan="1">110.00</td><td rowspan="1" colspan="1">O1—C7—C8</td><td rowspan="1" colspan="1">116.8 (4)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—H2B</td><td rowspan="1" colspan="1">110.00</td><td rowspan="1" colspan="1">O2—C7—C8</td><td rowspan="1" colspan="1">115.5 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H2A</td><td rowspan="1" colspan="1">110.00</td><td rowspan="1" colspan="1">Cl1—C8—Cl2</td><td rowspan="1" colspan="1">107.1 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—H2B</td><td rowspan="1" colspan="1">110.00</td><td rowspan="1" colspan="1">Cl1—C8—Cl3</td><td rowspan="1" colspan="1">107.2 (2)</td></tr><tr><td rowspan="1" colspan="1">H2A—C2—H2B</td><td rowspan="1" colspan="1">108.00</td><td rowspan="1" colspan="1">Cl1—C8—C7</td><td rowspan="1" colspan="1">112.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3A</td><td rowspan="1" colspan="1">109.00</td><td rowspan="1" colspan="1">Cl2—C8—Cl3</td><td rowspan="1" colspan="1">111.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3B</td><td rowspan="1" colspan="1">109.00</td><td rowspan="1" colspan="1">Cl2—C8—C7</td><td rowspan="1" colspan="1">107.5 (2)</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3A</td><td rowspan="1" colspan="1">109.00</td><td rowspan="1" colspan="1">Cl3—C8—C7</td><td rowspan="1" colspan="1">111.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3B</td><td rowspan="1" colspan="1">109.00</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">N1—C1—C2—C3</td><td rowspan="1" colspan="1">−178.3 (3)</td><td rowspan="1" colspan="1">C4—C5—C6—C1</td><td rowspan="1" colspan="1">−55.8 (5)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2—C3</td><td rowspan="1" colspan="1">−57.1 (4)</td><td rowspan="1" colspan="1">O1—C7—C8—Cl1</td><td rowspan="1" colspan="1">−15.1 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C6—C5</td><td rowspan="1" colspan="1">178.2 (3)</td><td rowspan="1" colspan="1">O1—C7—C8—Cl2</td><td rowspan="1" colspan="1">102.6 (4)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td><td rowspan="1" colspan="1">56.9 (4)</td><td rowspan="1" colspan="1">O1—C7—C8—Cl3</td><td rowspan="1" colspan="1">−135.5 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">56.5 (5)</td><td rowspan="1" colspan="1">O2—C7—C8—Cl1</td><td rowspan="1" colspan="1">165.9 (2)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">−55.9 (6)</td><td rowspan="1" colspan="1">O2—C7—C8—Cl2</td><td rowspan="1" colspan="1">−76.4 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td><td rowspan="1" colspan="1">55.4 (6)</td><td rowspan="1" colspan="1">O2—C7—C8—Cl3</td><td rowspan="1" colspan="1">45.6 (4)</td></tr></table></table-wrap></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, °)</title><table-wrap position="anchor" id="d1e1766"><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">N1—H1A···O1<sup>i</sup></td><td rowspan="1" colspan="1">0.85 (6)</td><td rowspan="1" colspan="1">1.96 (6)</td><td rowspan="1" colspan="1">2.788 (6)</td><td rowspan="1" colspan="1">167 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—H1B···O2<sup>ii</sup></td><td rowspan="1" colspan="1">0.82 (5)</td><td rowspan="1" colspan="1">1.96 (5)</td><td rowspan="1" colspan="1">2.770 (5)</td><td rowspan="1" colspan="1">168 (4)</td></tr><tr><td rowspan="1" colspan="1">N1—H1C···O1<sup>iii</sup></td><td rowspan="1" colspan="1">1.02 (4)</td><td rowspan="1" colspan="1">1.83 (4)</td><td rowspan="1" colspan="1">2.837 (4)</td><td rowspan="1" colspan="1">169 (4)</td></tr></table></table-wrap><p>Symmetry codes: (i) <italic>x</italic>−1, −<italic>y</italic>+1/2, <italic>z</italic>−1/2; (ii) <italic>x</italic>, −<italic>y</italic>+1/2, <italic>z</italic>−1/2; (iii) −<italic>x</italic>+1, <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">Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). <italic>J. Chem. Soc. Perkin Trans. 2</italic>, pp. S1–19.</mixed-citation></ref><ref id="bb2"><mixed-citation publication-type="other">Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). <italic>Angew. Chem. Int. Ed. Engl.</italic><bold>34</bold>, 1555–1573.</mixed-citation></ref><ref id="bb3"><mixed-citation publication-type="other">Bruker (2005). <italic>SADABS</italic> Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation></ref><ref id="bb4"><mixed-citation publication-type="other">Bruker (2007). <italic>APEX2</italic> and <italic>SAINT</italic> Bruker AXS Inc., Madison, Wisconsin, USA.</mixed-citation></ref><ref id="bb5"><mixed-citation publication-type="other">Farrugia, L. J. (1997). <italic>J. Appl. Cryst.</italic><bold>30</bold>, 565.</mixed-citation></ref><ref id="bb6"><mixed-citation publication-type="other">Farrugia, L. J. (1999). <italic>J. Appl. Cryst.</italic><bold>32</bold>, 837–838.</mixed-citation></ref><ref id="bb7"><mixed-citation publication-type="other">Jones, P. G. & Ahrens, B. (1998). <italic>Eur. J. Org. Chem.</italic><bold>8</bold>, 1687-1688.</mixed-citation></ref><ref id="bb8"><mixed-citation publication-type="other">Shahwar, D., Tahir, M. N., Ahmad, N., Khan, M. A. & Yasmeen, A. (2009). <italic>Acta Cryst.</italic> E<bold>65</bold>, o1312.</mixed-citation></ref><ref id="bb9"><mixed-citation publication-type="other">Sheldrick, G. M. (2008). <italic>Acta Cryst.</italic> A<bold>64</bold>, 112–122.</mixed-citation></ref><ref id="bb10"><mixed-citation publication-type="other">Spek, A. L. (2009). <italic>Acta Cryst.</italic> D<bold>65</bold>, 148–155.</mixed-citation></ref><ref id="bb11"><mixed-citation publication-type="other">Wang, J.-P., Cheng, X.-X., Wang, J.-G. & Chen, Q.-H. (2005). <italic>Acta Cryst.</italic> E<bold>61</bold>, o4006–o4007.</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">N1—H1<italic>A</italic>⋯O1<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.85 (6)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.96 (6)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.788 (6)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">167 (4)</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>B</italic>⋯O2<sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.82 (5)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.96 (5)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.770 (5)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">168 (4)</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>C</italic>⋯O1<sup>iii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.02 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.83 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.837 (4)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">169 (4)</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-65-o1313-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-65-o1313-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iii) <inline-formula><inline-graphic xlink:href="e-65-o1313-efi4.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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