Structural analysis of 2-iodobenzamide and 2-iodo-N-phenylbenzamide
Identifieur interne : 000983 ( Pmc/Corpus ); précédent : 000982; suivant : 000984Structural analysis of 2-iodobenzamide and 2-iodo-N-phenylbenzamide
Auteurs : Keshab M. Bairagi ; Vipin B. S. Kumar ; Subhrajyoti Bhandary ; Katharigatta N. Venugopala ; Susanta K. NayakSource :
- Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2018.
Abstract
The molecular and crystal structures of 2-iodo benzamide and 2-iodo-
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DOI: 10.1107/S2056989018010162
PubMed: 30116577
PubMed Central: 6072987
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Structural analysis of 2-iodobenzamide and 2-iodo-<italic>N</italic>-phenylbenzamide</title><author><name sortKey="Bairagi, Keshab M" sort="Bairagi, Keshab M" uniqKey="Bairagi K" first="Keshab M." last="Bairagi">Keshab M. Bairagi</name><affiliation><nlm:aff id="a">Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440 010, Maharashtra,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Kumar, Vipin B S" sort="Kumar, Vipin B S" uniqKey="Kumar V" first="Vipin B. S." last="Kumar">Vipin B. S. Kumar</name><affiliation><nlm:aff id="a">Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440 010, Maharashtra,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Bhandary, Subhrajyoti" sort="Bhandary, Subhrajyoti" uniqKey="Bhandary S" first="Subhrajyoti" last="Bhandary">Subhrajyoti Bhandary</name><affiliation><nlm:aff id="b">Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, Madhya Pradesh,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Venugopala, Katharigatta N" sort="Venugopala, Katharigatta N" uniqKey="Venugopala K" first="Katharigatta N." last="Venugopala">Katharigatta N. Venugopala</name><affiliation><nlm:aff id="c">Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001,<country>South Africa</country></nlm:aff></affiliation></author><author><name sortKey="Nayak, Susanta K" sort="Nayak, Susanta K" uniqKey="Nayak S" first="Susanta K." last="Nayak">Susanta K. Nayak</name><affiliation><nlm:aff id="a">Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440 010, Maharashtra,<country>India</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">30116577</idno><idno type="pmc">6072987</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6072987</idno><idno type="RBID">PMC:6072987</idno><idno type="doi">10.1107/S2056989018010162</idno><date when="2018">2018</date><idno type="wicri:Area/Pmc/Corpus">000983</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000983</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Structural analysis of 2-iodobenzamide and 2-iodo-<italic>N</italic>-phenylbenzamide</title><author><name sortKey="Bairagi, Keshab M" sort="Bairagi, Keshab M" uniqKey="Bairagi K" first="Keshab M." last="Bairagi">Keshab M. Bairagi</name><affiliation><nlm:aff id="a">Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440 010, Maharashtra,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Kumar, Vipin B S" sort="Kumar, Vipin B S" uniqKey="Kumar V" first="Vipin B. S." last="Kumar">Vipin B. S. Kumar</name><affiliation><nlm:aff id="a">Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440 010, Maharashtra,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Bhandary, Subhrajyoti" sort="Bhandary, Subhrajyoti" uniqKey="Bhandary S" first="Subhrajyoti" last="Bhandary">Subhrajyoti Bhandary</name><affiliation><nlm:aff id="b">Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, Madhya Pradesh,<country>India</country></nlm:aff></affiliation></author><author><name sortKey="Venugopala, Katharigatta N" sort="Venugopala, Katharigatta N" uniqKey="Venugopala K" first="Katharigatta N." last="Venugopala">Katharigatta N. Venugopala</name><affiliation><nlm:aff id="c">Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001,<country>South Africa</country></nlm:aff></affiliation></author><author><name sortKey="Nayak, Susanta K" sort="Nayak, Susanta K" uniqKey="Nayak S" first="Susanta K." last="Nayak">Susanta K. Nayak</name><affiliation><nlm:aff id="a">Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440 010, Maharashtra,<country>India</country></nlm:aff></affiliation></author></analytic><series><title level="j">Acta Crystallographica Section E: Crystallographic Communications</title><idno type="eISSN">2056-9890</idno><imprint><date when="2018">2018</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The molecular and crystal structures of 2-iodo benzamide and 2-iodo-<italic>N</italic>-phenylbenzamide are reported. In both crystals, N—H⋯O hydrogen bonds and C—I⋯π(ring) interactions stabilize the packing with additional C—H⋯π(ring) contacts found in the latter.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr E Crystallogr Commun</journal-id><journal-id journal-id-type="iso-abbrev">Acta Crystallogr E Crystallogr Commun</journal-id><journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id><journal-title-group><journal-title>Acta Crystallographica Section E: Crystallographic Communications</journal-title></journal-title-group><issn pub-type="epub">2056-9890</issn><publisher><publisher-name>International Union of Crystallography</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">30116577</article-id><article-id pub-id-type="pmc">6072987</article-id><article-id pub-id-type="publisher-id">sj5558</article-id><article-id pub-id-type="doi">10.1107/S2056989018010162</article-id><article-id pub-id-type="coden">ACSECI</article-id><article-id pub-id-type="pii">S2056989018010162</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject></subj-group></article-categories><title-group><article-title>Structural analysis of 2-iodobenzamide and 2-iodo-<italic>N</italic>-phenylbenzamide</article-title><alt-title><italic>C<sub>7</sub>H<sub>6</sub>INO and C<sub>13</sub>H<sub>10</sub>INO</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-7996-9601</contrib-id><name><surname>Bairagi</surname><given-names>Keshab M.</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Kumar</surname><given-names>Vipin B. S.</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Bhandary</surname><given-names>Subhrajyoti</given-names></name><xref ref-type="aff" rid="b">b</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0003-0680-1549</contrib-id><name><surname>Venugopala</surname><given-names>Katharigatta N.</given-names></name><xref ref-type="aff" rid="c">c</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-3175-9007</contrib-id><name><surname>Nayak</surname><given-names>Susanta K.</given-names></name><xref ref-type="aff" rid="a">a</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><aff id="a"><label>a</label>Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur 440 010, Maharashtra,<country>India</country></aff><aff id="b"><label>b</label>Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, Madhya Pradesh,<country>India</country></aff><aff id="c"><label>c</label>Department of Biotechnology and Food Technology, Durban University of Technology, Durban 4001,<country>South Africa</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>katharigattav@dut.ac.za</email>, <email>nksusa@gmail.com</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>8</month><year>2018</year></pub-date><pub-date pub-type="epub"><day>20</day><month>7</month><year>2018</year></pub-date><pub-date pub-type="pmc-release"><day>20</day><month>7</month><year>2018</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>74</volume><issue>Pt 8</issue><issue-id pub-id-type="publisher-id">e180800</issue-id><fpage>1130</fpage><lpage>1133</lpage><history><date date-type="received"><day>11</day><month>6</month><year>2018</year></date><date date-type="accepted"><day>13</day><month>7</month><year>2018</year></date></history><permissions><copyright-statement>© Bairagi et al. 2018</copyright-statement><copyright-year>2018</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 (CC-BY) Licence, which permits unrestricted
use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p><ali:license_ref>http://creativecommons.org/licenses/by/2.0/uk/</ali:license_ref></license></permissions><self-uri xlink:href="https://doi.org/10.1107/S2056989018010162">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract abstract-type="toc"><p>The molecular and crystal structures of 2-iodo benzamide and 2-iodo-<italic>N</italic>-phenylbenzamide are reported. In both crystals, N—H⋯O hydrogen bonds and C—I⋯π(ring) interactions stabilize the packing with additional C—H⋯π(ring) contacts found in the latter.</p></abstract><abstract><p>The title compounds, 2-iodobenzamide, C<sub>7</sub>H<sub>6</sub>INO (I), and 2-iodo-<italic>N</italic>-phenylbenzamide, C<sub>13</sub>H<sub>10</sub>INO (II), were both synthesized from 2-iodobenzoic acid. In the crystal structure of (I), N—H⋯O and hydrogen bonds form two sets of closed rings, generating dimers and tetramers. These combine with C—I⋯π(ring) halogen bonds to form sheets of molecules in the <italic>bc</italic> plane. For (II), N—H⋯O hydrogen bonds form chains along the <italic>a</italic>-axis direction, while inversion-related C—I⋯π(ring) contacts supported by C—H⋯π(ring) interactions generate sheets of molecules along the <italic>ab</italic> diagonal.</p></abstract><kwd-group><kwd>crystal structure</kwd><kwd>benzamide</kwd><kwd>dimer</kwd><kwd>tetramer</kwd><kwd>hydrogen bonds</kwd><kwd>C—I⋯π(ring) interactions</kwd></kwd-group><funding-group><award-group><funding-source>Visvesvaraya Technological University</funding-source></award-group><award-group><funding-source>National Research Foundation</funding-source><award-id>91995</award-id><award-id>96807</award-id></award-group><award-group><funding-source>Durban University of Technology</funding-source></award-group><funding-statement>This work was funded by <funding-source>Visvesvaraya Technological University</funding-source> grant . <funding-source>National Research Foundation</funding-source> grants <award-id>91995</award-id> and <award-id>96807</award-id>. <funding-source>Durban University of Technology</funding-source> grant . </funding-statement></funding-group><counts><page-count count="4"></page-count></counts></article-meta></front><body><sec id="sec1"><title>Chemical context </title><p>Aromatic amides can be found in a wide range of aromatic molecules and they also serve as intermediates in the production of many pharmaceutical compounds (Suchetan <italic>et al.</italic>, 2016<xref ref-type="bibr" rid="bb22"> ▸</xref>). Aromatic amides and <italic>N</italic>-aryl amides display a wide spectrum of pharmacological properties and are used as antibacterial (Ragavan <italic>et al.</italic>, 2010<xref ref-type="bibr" rid="bb17"> ▸</xref>), analgesic (Starmer <italic>et al.</italic>, 1971<xref ref-type="bibr" rid="bb21"> ▸</xref>), antiviral (Hu <italic>et al.</italic>, 2008<xref ref-type="bibr" rid="bb7"> ▸</xref>), anti-inflammatory (Kalgutkar <italic>et al.</italic>, 2000<xref ref-type="bibr" rid="bb9"> ▸</xref>) and anti-cancer (Pradidphol <italic>et al.</italic>, 2012<xref ref-type="bibr" rid="bb16"> ▸</xref>) agents. Furthermore, <italic>N</italic>-aryl amides are known to act as anti-tumor agents against a broad spectrum of human tumors (Abdou <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb1"> ▸</xref>). In view of their potential importance, the title compounds (I)<xref ref-type="chem" rid="scheme1"></xref> and (II)<xref ref-type="chem" rid="scheme1"></xref> were synthesized and we report herein a comparison of their structures.<chem-struct id="scheme1"><graphic xlink:href="e-74-01130-scheme1.jpg" position="float" orientation="portrait"></graphic></chem-struct></p></sec><sec id="sec2"><title>Structural commentary </title><p>Both compounds (I)<xref ref-type="chem" rid="scheme1"></xref> and (II)<xref ref-type="chem" rid="scheme1"></xref> crystallize with one molecule in the asymmetric unit (<italic>Z</italic>′ = 1). The molecular structures of the molecules are shown in Figs. 1<xref ref-type="fig" rid="fig1"> ▸</xref> and 2<xref ref-type="fig" rid="fig2"> ▸</xref>, respectively. In (I)<xref ref-type="chem" rid="scheme1"></xref> the aromatic ring is inclined to the O1/C1/N1 plane of the amide by 44.37 (1)° whereas in (II)<xref ref-type="chem" rid="scheme1"></xref> the two aromatic rings are almost orthogonal with an angle of 79.84 (6)° between them. The iodobenzene ring plane is inclined to the O1/C1/N1 amide plane by 52.01 (1)°, somewhat similar to the inclination found for (I)<xref ref-type="chem" rid="scheme1"></xref>, while the phenyl ring of the amide is inclined by 28.45 (5)° to this plane.</p></sec><sec id="sec3"><title>Supramolecular features </title><p>In the crystal structure of compound (I)<xref ref-type="chem" rid="scheme1"></xref>, strong classical N1—H1<italic>A</italic>⋯O1 and N1—H1<italic>B</italic>⋯O1 hydrogen bonds, Table 1<xref ref-type="table" rid="table1"> ▸</xref>, arrange the molecules in two linked sets of closed rings, forming both dimers with an <inline-formula><inline-graphic xlink:href="e-74-01130-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8) graph-set motif and tetramers that enclose <inline-formula><inline-graphic xlink:href="e-74-01130-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>(8) rings (Etter <italic>et al.</italic>, 1990<xref ref-type="bibr" rid="bb3"> ▸</xref>). These contacts form chains of molecules along the <italic>a</italic>-axis direction (Fig. 3<xref ref-type="fig" rid="fig3"> ▸</xref>). In addition, C3—I1⋯<italic>Cg</italic>1 halogen bonds, Table 1<xref ref-type="table" rid="table1"> ▸</xref>, combine with the previously mentioned inversion dimers to generate sheets of molecules in the <italic>bc</italic> plane (Fig. 4<xref ref-type="fig" rid="fig4"> ▸</xref>).</p><p>For compound (II)<xref ref-type="chem" rid="scheme1"></xref>, the absence of a second H atom on the N1 amine nitrogen atom limits the formation of classical hydrogen bonds to N1—H1⋯O1 contacts that generate <italic>C</italic>(4) molecular chains along the <italic>a</italic>-axis direction (Fig. 5<xref ref-type="fig" rid="fig5"> ▸</xref>, Table 2<xref ref-type="table" rid="table2"> ▸</xref>). Additional weak inversion-related C3—I1⋯<italic>Cg</italic>2 interactions (Table 2<xref ref-type="table" rid="table2"> ▸</xref>), in this instance also supported by C6—H6⋯<italic>Cg</italic>2 contacts that also lie about an inversion centre, form sheets of molecules along the <italic>ab</italic> diagonal (Fig. 6<xref ref-type="fig" rid="fig6"> ▸</xref>, Table 2<xref ref-type="table" rid="table2"> ▸</xref>).</p></sec><sec id="sec4"><title>Database survey </title><p>A search for the crystal structures of 2-iodobenzamide and 2-iodo-<italic>N</italic>-phenylbenzamide was carried out in the Cambridge Structural Database (Conquest Version 1.17; CSD Version 5.39, last update November 2017; Groom <italic>et al.</italic>, 2016<xref ref-type="bibr" rid="bb6"> ▸</xref>). Compound (I)<xref ref-type="chem" rid="scheme1"></xref> was found to have been previously reported from film data (IBNZAM; Nakata <italic>et al.</italic>, 1976<xref ref-type="bibr" rid="bb13"> ▸</xref>), but there were no hits for compound (II)<xref ref-type="chem" rid="scheme1"></xref>. Four other related structures were observed: two fluorine-substituted 2-iodobenzamides, FAHSAK and FAHSIS (Nayak <italic>et al.</italic>, 2012<xref ref-type="bibr" rid="bb15"> ▸</xref>) and two nitro substituted 2-iodobenzamides, TAQBIX (Garden <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb5"> ▸</xref>) and WAWMAJ (Wardell <italic>et al.</italic>, 2005<xref ref-type="bibr" rid="bb23"> ▸</xref>).</p></sec><sec id="sec5"><title>Synthesis and crystallization </title><p>The synthesis of the title compounds was carried out using a reported procedure (Jursic & Zdravkovski, 1993<xref ref-type="bibr" rid="bb8"> ▸</xref>; Kavala <italic>et al.</italic>, 2012<xref ref-type="bibr" rid="bb10"> ▸</xref>; Mao <italic>et al.</italic>, 2012<xref ref-type="bibr" rid="bb12"> ▸</xref>). Single crystals for both compounds were grown by the slow evaporation method from dichloromethane and hexane (<italic>v</italic>/<italic>v</italic> 1:1) at low temperature for (I)<xref ref-type="chem" rid="scheme1"></xref>, whereas those for compound (II)<xref ref-type="chem" rid="scheme1"></xref> were obtained from acetonitrile solvent at room temperature. The melting points of (I)<xref ref-type="chem" rid="scheme1"></xref> and (II)<xref ref-type="chem" rid="scheme1"></xref> are 398.2 and 419.6 K, respectively. Infra-red (IR) spectra confirm the presence of various functional groups as follows: compound (I)<xref ref-type="chem" rid="scheme1"></xref> (cm<sup>−1</sup>): N—H = 3362, 3177, C=O = 1644, C=C = 1581–1470, <italic>ortho</italic>-substituted ring = 734; compound (II)<xref ref-type="chem" rid="scheme1"></xref> (cm<sup>−1</sup>): N—H = 3235, C<italic>sp</italic><sup>2</sup>—H = 3037, C=O = 1646, C=C = 1536–1488, <italic>ortho</italic>-substituted ring = 752, N—H bending = 1597.</p></sec><sec id="sec6"><title>Refinement </title><p>Crystal data, data collection and structure refinement details are summarized in Table 3<xref ref-type="table" rid="table3"> ▸</xref>. All H atoms were refined using a riding model with <italic>d</italic>(N—H) = 0.86 Å, <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(N) and <italic>d</italic>(C—H) = 0.93 Å, <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(C) for (I)<xref ref-type="chem" rid="scheme1"></xref> and <italic>d</italic>(N—H) = 0.88 Å, <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(N) and <italic>d</italic>(C—H) = 0.95 Å, <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(C) for (II)<xref ref-type="chem" rid="scheme1"></xref>.</p></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data"><p>Crystal structure: contains datablock(s) global, I, II. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018010162/sj5558sup1.cif">10.1107/S2056989018010162/sj5558sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-74-01130-sup1.cif" orientation="portrait" id="d35e168" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018010162/sj5558Isup2.hkl">10.1107/S2056989018010162/sj5558Isup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-74-01130-Isup2.hkl" orientation="portrait" id="d35e175" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) II. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018010162/sj5558IIsup3.hkl">10.1107/S2056989018010162/sj5558IIsup3.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-74-01130-IIsup3.hkl" orientation="portrait" id="d35e182" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-74-01130-Isup4.cml"><caption><p>Click here for additional data file.</p></caption></media><p>Supporting information file. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018010162/sj5558Isup4.cml">10.1107/S2056989018010162/sj5558Isup4.cml</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><media xlink:href="e-74-01130-IIsup5.cml"><caption><p>Click here for additional data file.</p></caption></media><p>Supporting information file. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989018010162/sj5558IIsup5.cml">10.1107/S2056989018010162/sj5558IIsup5.cml</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><p>CCDC references: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1855731">1855731</ext-link>, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1855730">1855730</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><p>Additional supporting information: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?sj5558&file=sj5558sup0.html&mime=text/html"> crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?sj5558sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?sj5558&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><ack><p>We thank Dr Deepak Chopra, IISER, Bhopal for the single-crystal X-ray data collection.</p></ack><app-group><app><title>supplementary crystallographic information</title><sec id="d1e151" sec-type="tablewrapcrystaldatalong"><label>2-Iodobenzamide (I) </label><title>Crystal data</title><table-wrap position="anchor" id="d1e160"><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>7</sub>H<sub>6</sub>INO</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 464</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 247.03</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 2.137 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>2<sub>1</sub>/<italic>n</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"><italic>a</italic> = 5.0531 (2) Å</td><td rowspan="1" colspan="1">Cell parameters from 1504 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 11.4478 (5) Å</td><td rowspan="1" colspan="1">θ = 2.3–26.0°</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 13.2945 (5) Å</td><td rowspan="1" colspan="1">µ = 4.10 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">β = 93.245 (1)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 296 K</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 767.81 (5) Å<sup>3</sup></td><td rowspan="1" colspan="1">Plate, colorless</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 4</td><td rowspan="1" colspan="1">0.23 × 0.22 × 0.21 mm</td></tr></table></table-wrap></sec><sec id="d1e272" sec-type="tablewrapdatacollectionlong"><label>2-Iodobenzamide (I) </label><title>Data collection</title><table-wrap position="anchor" id="d1e281"><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 DUO diffractometer</td><td rowspan="1" colspan="1">1504 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">1461 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">Graphite monochromator</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.021</td></tr><tr><td rowspan="1" colspan="1">ω scans</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 26.0°, θ<sub>min</sub> = 2.4°</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (SADABS; Bruker, 2014)</td><td rowspan="1" colspan="1"><italic>h</italic> = −6→6</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.429, <italic>T</italic><sub>max</sub> = 0.456</td><td rowspan="1" colspan="1"><italic>k</italic> = −14→11</td></tr><tr><td rowspan="1" colspan="1">5827 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −15→16</td></tr></table></table-wrap></sec><sec id="d1e383" sec-type="tablewraprefinementdatalong"><label>2-Iodobenzamide (I) </label><title>Refinement</title><table-wrap position="anchor" id="d1e392"><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">Hydrogen site location: inferred from neighbouring sites</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.014</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0075<italic>P</italic>)<sup>2</sup> + 0.6908<italic>P</italic>] where <italic>P</italic> = (<italic>F</italic><sub>o</sub><sup>2</sup> + 2<italic>F</italic><sub>c</sub><sup>2</sup>)/3</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.033</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> = 0.002</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.16</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.45 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">1504 reflections</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.35 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">92 parameters</td><td rowspan="1" colspan="1">Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc<sup>*</sup>=kFc[1+0.001xFc<sup>2</sup>λ<sup>3</sup>/sin(2θ)]<sup>-1/4</sup></td></tr><tr><td rowspan="1" colspan="1">0 restraints</td><td rowspan="1" colspan="1">Extinction coefficient: 0.0170 (5)</td></tr></table></table-wrap></sec><sec id="d1e554" sec-type="specialdetails"><label>2-Iodobenzamide (I) </label><title>Special details</title><table-wrap position="anchor" id="d1e564"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td></tr></table></table-wrap></sec><sec id="d1e573" sec-type="tablewrapcoords"><label>2-Iodobenzamide (I) </label><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e585"><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">I1</td><td rowspan="1" colspan="1">0.14922 (2)</td><td rowspan="1" colspan="1">0.55570 (2)</td><td rowspan="1" colspan="1">0.18090 (2)</td><td rowspan="1" colspan="1">0.01703 (7)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.3073 (3)</td><td rowspan="1" colspan="1">0.43218 (14)</td><td rowspan="1" colspan="1">0.39426 (11)</td><td rowspan="1" colspan="1">0.0177 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.7508 (3)</td><td rowspan="1" colspan="1">0.44020 (16)</td><td rowspan="1" colspan="1">0.41536 (14)</td><td rowspan="1" colspan="1">0.0168 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1A</td><td rowspan="1" colspan="1">0.7438</td><td rowspan="1" colspan="1">0.4650</td><td rowspan="1" colspan="1">0.4762</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1B</td><td rowspan="1" colspan="1">0.9018</td><td rowspan="1" colspan="1">0.4297</td><td rowspan="1" colspan="1">0.3900</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.6303 (4)</td><td rowspan="1" colspan="1">0.2793 (2)</td><td rowspan="1" colspan="1">0.06578 (17)</td><td rowspan="1" colspan="1">0.0219 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">0.6514</td><td rowspan="1" colspan="1">0.2473</td><td rowspan="1" colspan="1">0.0024</td><td rowspan="1" colspan="1">0.026*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.7846 (4)</td><td rowspan="1" colspan="1">0.23997 (19)</td><td rowspan="1" colspan="1">0.14775 (17)</td><td rowspan="1" colspan="1">0.0202 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6</td><td rowspan="1" colspan="1">0.9113</td><td rowspan="1" colspan="1">0.1824</td><td rowspan="1" colspan="1">0.1396</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.7504 (4)</td><td rowspan="1" colspan="1">0.28652 (19)</td><td rowspan="1" colspan="1">0.24225 (17)</td><td rowspan="1" colspan="1">0.0165 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7</td><td rowspan="1" colspan="1">0.8555</td><td rowspan="1" colspan="1">0.2598</td><td rowspan="1" colspan="1">0.2972</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.5610 (4)</td><td rowspan="1" colspan="1">0.37276 (18)</td><td rowspan="1" colspan="1">0.25648 (15)</td><td rowspan="1" colspan="1">0.0125 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.5297 (4)</td><td rowspan="1" colspan="1">0.41830 (18)</td><td rowspan="1" colspan="1">0.36086 (15)</td><td rowspan="1" colspan="1">0.0125 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.4440 (4)</td><td rowspan="1" colspan="1">0.3662 (2)</td><td rowspan="1" colspan="1">0.07746 (16)</td><td rowspan="1" colspan="1">0.0193 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">0.3416</td><td rowspan="1" colspan="1">0.3931</td><td rowspan="1" colspan="1">0.0219</td><td rowspan="1" colspan="1">0.023*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.4101 (4)</td><td rowspan="1" colspan="1">0.41317 (18)</td><td rowspan="1" colspan="1">0.17218 (16)</td><td rowspan="1" colspan="1">0.0138 (4)</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e802" sec-type="tablewrapadps"><label>2-Iodobenzamide (I) </label><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e814"><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">I1</td><td rowspan="1" colspan="1">0.01454 (9)</td><td rowspan="1" colspan="1">0.01736 (10)</td><td rowspan="1" colspan="1">0.01910 (10)</td><td rowspan="1" colspan="1">0.00237 (5)</td><td rowspan="1" colspan="1">0.00030 (5)</td><td rowspan="1" colspan="1">0.00353 (5)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0082 (7)</td><td rowspan="1" colspan="1">0.0300 (9)</td><td rowspan="1" colspan="1">0.0152 (8)</td><td rowspan="1" colspan="1">−0.0007 (6)</td><td rowspan="1" colspan="1">0.0019 (5)</td><td rowspan="1" colspan="1">−0.0026 (6)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0094 (8)</td><td rowspan="1" colspan="1">0.0280 (11)</td><td rowspan="1" colspan="1">0.0132 (9)</td><td rowspan="1" colspan="1">−0.0003 (7)</td><td rowspan="1" colspan="1">0.0021 (6)</td><td rowspan="1" colspan="1">−0.0044 (8)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0286 (12)</td><td rowspan="1" colspan="1">0.0200 (11)</td><td rowspan="1" colspan="1">0.0177 (12)</td><td rowspan="1" colspan="1">−0.0038 (9)</td><td rowspan="1" colspan="1">0.0070 (9)</td><td rowspan="1" colspan="1">−0.0071 (9)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0210 (11)</td><td rowspan="1" colspan="1">0.0125 (11)</td><td rowspan="1" colspan="1">0.0277 (12)</td><td rowspan="1" colspan="1">−0.0010 (9)</td><td rowspan="1" colspan="1">0.0085 (9)</td><td rowspan="1" colspan="1">−0.0048 (9)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0138 (9)</td><td rowspan="1" colspan="1">0.0140 (10)</td><td rowspan="1" colspan="1">0.0220 (11)</td><td rowspan="1" colspan="1">−0.0022 (8)</td><td rowspan="1" colspan="1">0.0024 (8)</td><td rowspan="1" colspan="1">0.0013 (9)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0100 (9)</td><td rowspan="1" colspan="1">0.0122 (10)</td><td rowspan="1" colspan="1">0.0154 (10)</td><td rowspan="1" colspan="1">−0.0034 (7)</td><td rowspan="1" colspan="1">0.0019 (7)</td><td rowspan="1" colspan="1">−0.0003 (8)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0118 (9)</td><td rowspan="1" colspan="1">0.0117 (9)</td><td rowspan="1" colspan="1">0.0142 (10)</td><td rowspan="1" colspan="1">−0.0002 (8)</td><td rowspan="1" colspan="1">0.0015 (7)</td><td rowspan="1" colspan="1">0.0036 (8)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0213 (10)</td><td rowspan="1" colspan="1">0.0226 (12)</td><td rowspan="1" colspan="1">0.0140 (11)</td><td rowspan="1" colspan="1">−0.0042 (9)</td><td rowspan="1" colspan="1">−0.0002 (8)</td><td rowspan="1" colspan="1">−0.0012 (9)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0120 (9)</td><td rowspan="1" colspan="1">0.0122 (10)</td><td rowspan="1" colspan="1">0.0173 (11)</td><td rowspan="1" colspan="1">−0.0019 (8)</td><td rowspan="1" colspan="1">0.0025 (8)</td><td rowspan="1" colspan="1">0.0005 (8)</td></tr></table></table-wrap></sec><sec id="d1e1030" sec-type="tablewrapgeomlong"><label>2-Iodobenzamide (I) </label><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e1040"><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">I1—C3</td><td rowspan="1" colspan="1">2.105 (2)</td><td rowspan="1" colspan="1">C6—C7</td><td rowspan="1" colspan="1">1.385 (3)</td></tr><tr><td rowspan="1" colspan="1">O1—C1</td><td rowspan="1" colspan="1">1.242 (2)</td><td rowspan="1" colspan="1">C6—H6</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N1—C1</td><td rowspan="1" colspan="1">1.321 (3)</td><td rowspan="1" colspan="1">C7—C2</td><td rowspan="1" colspan="1">1.395 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—H1A</td><td rowspan="1" colspan="1">0.8600</td><td rowspan="1" colspan="1">C7—H7</td><td rowspan="1" colspan="1">0.9300</td></tr><tr><td rowspan="1" colspan="1">N1—H1B</td><td rowspan="1" colspan="1">0.8600</td><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.398 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.379 (3)</td><td rowspan="1" colspan="1">C2—C1</td><td rowspan="1" colspan="1">1.499 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C4</td><td rowspan="1" colspan="1">1.384 (3)</td><td rowspan="1" colspan="1">C4—C3</td><td rowspan="1" colspan="1">1.389 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.9300</td><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9300</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—H1A</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">C7—C2—C3</td><td rowspan="1" colspan="1">118.20 (19)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—H1B</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">C7—C2—C1</td><td rowspan="1" colspan="1">118.73 (18)</td></tr><tr><td rowspan="1" colspan="1">H1A—N1—H1B</td><td rowspan="1" colspan="1">120.0</td><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">123.07 (18)</td></tr><tr><td rowspan="1" colspan="1">C6—C5—C4</td><td rowspan="1" colspan="1">120.2 (2)</td><td rowspan="1" colspan="1">O1—C1—N1</td><td rowspan="1" colspan="1">122.29 (19)</td></tr><tr><td rowspan="1" colspan="1">C6—C5—H5</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">O1—C1—C2</td><td rowspan="1" colspan="1">121.37 (18)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">N1—C1—C2</td><td rowspan="1" colspan="1">116.32 (16)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C7</td><td rowspan="1" colspan="1">119.8 (2)</td><td rowspan="1" colspan="1">C5—C4—C3</td><td rowspan="1" colspan="1">120.0 (2)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—H6</td><td rowspan="1" colspan="1">120.1</td><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">C7—C6—H6</td><td rowspan="1" colspan="1">120.1</td><td rowspan="1" colspan="1">C3—C4—H4</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">C6—C7—C2</td><td rowspan="1" colspan="1">121.1 (2)</td><td rowspan="1" colspan="1">C4—C3—C2</td><td rowspan="1" colspan="1">120.61 (19)</td></tr><tr><td rowspan="1" colspan="1">C6—C7—H7</td><td rowspan="1" colspan="1">119.4</td><td rowspan="1" colspan="1">C4—C3—I1</td><td rowspan="1" colspan="1">117.38 (16)</td></tr><tr><td rowspan="1" colspan="1">C2—C7—H7</td><td rowspan="1" colspan="1">119.4</td><td rowspan="1" colspan="1">C2—C3—I1</td><td rowspan="1" colspan="1">121.81 (15)</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">C4—C5—C6—C7</td><td rowspan="1" colspan="1">0.9 (3)</td><td rowspan="1" colspan="1">C6—C5—C4—C3</td><td rowspan="1" colspan="1">−0.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C6—C7—C2</td><td rowspan="1" colspan="1">0.2 (3)</td><td rowspan="1" colspan="1">C5—C4—C3—C2</td><td rowspan="1" colspan="1">−0.6 (3)</td></tr><tr><td rowspan="1" colspan="1">C6—C7—C2—C3</td><td rowspan="1" colspan="1">−1.5 (3)</td><td rowspan="1" colspan="1">C5—C4—C3—I1</td><td rowspan="1" colspan="1">174.29 (16)</td></tr><tr><td rowspan="1" colspan="1">C6—C7—C2—C1</td><td rowspan="1" colspan="1">178.91 (18)</td><td rowspan="1" colspan="1">C7—C2—C3—C4</td><td rowspan="1" colspan="1">1.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C7—C2—C1—O1</td><td rowspan="1" colspan="1">−135.1 (2)</td><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">−178.75 (18)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1—O1</td><td rowspan="1" colspan="1">45.3 (3)</td><td rowspan="1" colspan="1">C7—C2—C3—I1</td><td rowspan="1" colspan="1">−172.99 (14)</td></tr><tr><td rowspan="1" colspan="1">C7—C2—C1—N1</td><td rowspan="1" colspan="1">43.5 (3)</td><td rowspan="1" colspan="1">C1—C2—C3—I1</td><td rowspan="1" colspan="1">6.6 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1—N1</td><td rowspan="1" colspan="1">−136.1 (2)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e1323" sec-type="tablewraphbondslong"><label>2-Iodobenzamide (I) </label><title>Hydrogen-bond geometry (Å, º)</title><p>Cg1 is the centroid of the C2–C7 phenyl ring.</p><table-wrap position="anchor" id="d1e1337"><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—H1<italic>A</italic>···O1<sup>i</sup></td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">2.11</td><td rowspan="1" colspan="1">2.951 (2)</td><td rowspan="1" colspan="1">164</td></tr><tr><td rowspan="1" colspan="1">N1—H1<italic>B</italic>···O1<sup>ii</sup></td><td rowspan="1" colspan="1">0.86</td><td rowspan="1" colspan="1">2.05</td><td rowspan="1" colspan="1">2.843 (2)</td><td rowspan="1" colspan="1">154</td></tr><tr><td rowspan="1" colspan="1">C3—I1···<italic>Cg</italic>1<sup>iii</sup></td><td rowspan="1" colspan="1">2.11 (1)</td><td rowspan="1" colspan="1">3.99 (1)</td><td rowspan="1" colspan="1">5.877 (2)</td><td rowspan="1" colspan="1">148 (1)</td></tr></table></table-wrap><p>Symmetry codes: (i) −<italic>x</italic>+1, −<italic>y</italic>+1, −<italic>z</italic>+1; (ii) <italic>x</italic>+1, <italic>y</italic>, <italic>z</italic>; (iii) −<italic>x</italic>+1/2, <italic>y</italic>+1/2, −<italic>z</italic>+1/2.</p></sec><sec id="d1e1478" sec-type="tablewrapcrystaldatalong"><label>2-Iodo-<italic>N</italic>-phenylbenzamide (II) </label><title>Crystal data</title><table-wrap position="anchor" id="d1e1487"><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>13</sub>H<sub>10</sub>INO</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> = 323.12</td><td rowspan="1" colspan="1"><italic>F</italic>(000) = 312</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> = 1.829 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 5.1225 (2) Å</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>b</italic> = 10.4572 (4) Å</td><td rowspan="1" colspan="1">Cell parameters from 2309 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 12.2167 (5) Å</td><td rowspan="1" colspan="1">θ = 1.9–26.0°</td></tr><tr><td rowspan="1" colspan="1">α = 66.034 (2)°</td><td rowspan="1" colspan="1">µ = 2.71 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">β = 78.882 (2)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 120 K</td></tr><tr><td rowspan="1" colspan="1">γ = 85.760 (2)°</td><td rowspan="1" colspan="1">Plate, colorless</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 586.76 (4) Å<sup>3</sup></td><td rowspan="1" colspan="1">0.23 × 0.22 × 0.21 mm</td></tr></table></table-wrap></sec><sec id="d1e1604" sec-type="tablewrapdatacollectionlong"><label>2-Iodo-<italic>N</italic>-phenylbenzamide (II) </label><title>Data collection</title><table-wrap position="anchor" id="d1e1613"><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 DUO diffractometer</td><td rowspan="1" colspan="1">2309 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td><td rowspan="1" colspan="1">2278 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">Graphite monochromator</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.018</td></tr><tr><td rowspan="1" colspan="1">ω scans</td><td rowspan="1" colspan="1">θ<sub>max</sub> = 26.0°, θ<sub>min</sub> = 1.9°</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (SADABS; Bruker, 2014)</td><td rowspan="1" colspan="1"><italic>h</italic> = −6→6</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.546, <italic>T</italic><sub>max</sub> = 0.570</td><td rowspan="1" colspan="1"><italic>k</italic> = −12→12</td></tr><tr><td rowspan="1" colspan="1">13292 measured reflections</td><td rowspan="1" colspan="1"><italic>l</italic> = −15→14</td></tr></table></table-wrap></sec><sec id="d1e1715" sec-type="tablewraprefinementdatalong"><label>2-Iodo-<italic>N</italic>-phenylbenzamide (II) </label><title>Refinement</title><table-wrap position="anchor" id="d1e1724"><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">0 restraints</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.017</td><td rowspan="1" colspan="1">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.042</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.0207<italic>P</italic>)<sup>2</sup> + 0.7193<italic>P</italic>] where <italic>P</italic> = (<italic>F</italic><sub>o</sub><sup>2</sup> + 2<italic>F</italic><sub>c</sub><sup>2</sup>)/3</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.08</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1">2309 reflections</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.81 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">145 parameters</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −0.48 e Å<sup>−</sup><sup>3</sup></td></tr></table></table-wrap></sec><sec id="d1e1866" sec-type="specialdetails"><label>2-Iodo-<italic>N</italic>-phenylbenzamide (II) </label><title>Special details</title><table-wrap position="anchor" id="d1e1876"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td></tr></table></table-wrap></sec><sec id="d1e1885" sec-type="tablewrapcoords"><label>2-Iodo-<italic>N</italic>-phenylbenzamide (II) </label><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e1897"><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">I1</td><td rowspan="1" colspan="1">−0.30400 (3)</td><td rowspan="1" colspan="1">0.03723 (2)</td><td rowspan="1" colspan="1">0.77480 (2)</td><td rowspan="1" colspan="1">0.01972 (6)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">−0.1224 (3)</td><td rowspan="1" colspan="1">0.31161 (18)</td><td rowspan="1" colspan="1">0.51921 (14)</td><td rowspan="1" colspan="1">0.0233 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.3285 (3)</td><td rowspan="1" colspan="1">0.2852 (2)</td><td rowspan="1" colspan="1">0.49180 (16)</td><td rowspan="1" colspan="1">0.0169 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H1</td><td rowspan="1" colspan="1">0.4668</td><td rowspan="1" colspan="1">0.2731</td><td rowspan="1" colspan="1">0.5279</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0875 (4)</td><td rowspan="1" colspan="1">0.2939 (2)</td><td rowspan="1" colspan="1">0.55727 (19)</td><td rowspan="1" colspan="1">0.0161 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0968 (4)</td><td rowspan="1" colspan="1">0.2802 (2)</td><td rowspan="1" colspan="1">0.68392 (19)</td><td rowspan="1" colspan="1">0.0148 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">−0.0677 (4)</td><td rowspan="1" colspan="1">0.1861 (2)</td><td rowspan="1" colspan="1">0.7861 (2)</td><td rowspan="1" colspan="1">0.0156 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">−0.0629 (4)</td><td rowspan="1" colspan="1">0.1793 (2)</td><td rowspan="1" colspan="1">0.9014 (2)</td><td rowspan="1" colspan="1">0.0194 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H4</td><td rowspan="1" colspan="1">−0.1751</td><td rowspan="1" colspan="1">0.1151</td><td rowspan="1" colspan="1">0.9704</td><td rowspan="1" colspan="1">0.023*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.1069 (4)</td><td rowspan="1" colspan="1">0.2670 (2)</td><td rowspan="1" colspan="1">0.9157 (2)</td><td rowspan="1" colspan="1">0.0206 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">0.1091</td><td rowspan="1" colspan="1">0.2632</td><td rowspan="1" colspan="1">0.9945</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.2728 (4)</td><td rowspan="1" colspan="1">0.3597 (2)</td><td rowspan="1" colspan="1">0.8154 (2)</td><td rowspan="1" colspan="1">0.0198 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H6</td><td rowspan="1" colspan="1">0.3893</td><td rowspan="1" colspan="1">0.4191</td><td rowspan="1" colspan="1">0.8255</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.2685 (4)</td><td rowspan="1" colspan="1">0.3657 (2)</td><td rowspan="1" colspan="1">0.7005 (2)</td><td rowspan="1" colspan="1">0.0169 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H7</td><td rowspan="1" colspan="1">0.3838</td><td rowspan="1" colspan="1">0.4289</td><td rowspan="1" colspan="1">0.6321</td><td rowspan="1" colspan="1">0.020*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.3800 (4)</td><td rowspan="1" colspan="1">0.2938 (2)</td><td rowspan="1" colspan="1">0.37055 (19)</td><td rowspan="1" colspan="1">0.0159 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.2215 (4)</td><td rowspan="1" colspan="1">0.3717 (2)</td><td rowspan="1" colspan="1">0.2855 (2)</td><td rowspan="1" colspan="1">0.0180 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9</td><td rowspan="1" colspan="1">0.0683</td><td rowspan="1" colspan="1">0.4185</td><td rowspan="1" colspan="1">0.3083</td><td rowspan="1" colspan="1">0.022*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.2897 (4)</td><td rowspan="1" colspan="1">0.3802 (2)</td><td rowspan="1" colspan="1">0.1671 (2)</td><td rowspan="1" colspan="1">0.0191 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">0.1821</td><td rowspan="1" colspan="1">0.4334</td><td rowspan="1" colspan="1">0.1089</td><td rowspan="1" colspan="1">0.023*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.5124 (4)</td><td rowspan="1" colspan="1">0.3123 (2)</td><td rowspan="1" colspan="1">0.1323 (2)</td><td rowspan="1" colspan="1">0.0203 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H11</td><td rowspan="1" colspan="1">0.5579</td><td rowspan="1" colspan="1">0.3190</td><td rowspan="1" colspan="1">0.0510</td><td rowspan="1" colspan="1">0.024*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.6677 (4)</td><td rowspan="1" colspan="1">0.2343 (2)</td><td rowspan="1" colspan="1">0.2180 (2)</td><td rowspan="1" colspan="1">0.0209 (5)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H12</td><td rowspan="1" colspan="1">0.8204</td><td rowspan="1" colspan="1">0.1873</td><td rowspan="1" colspan="1">0.1952</td><td rowspan="1" colspan="1">0.025*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.6024 (4)</td><td rowspan="1" colspan="1">0.2245 (2)</td><td rowspan="1" colspan="1">0.3364 (2)</td><td rowspan="1" colspan="1">0.0192 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.7094</td><td rowspan="1" colspan="1">0.1703</td><td rowspan="1" colspan="1">0.3945</td><td rowspan="1" colspan="1">0.023*</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e2245" sec-type="tablewrapadps"><label>2-Iodo-<italic>N</italic>-phenylbenzamide (II) </label><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e2257"><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">I1</td><td rowspan="1" colspan="1">0.01580 (8)</td><td rowspan="1" colspan="1">0.01876 (9)</td><td rowspan="1" colspan="1">0.02535 (9)</td><td rowspan="1" colspan="1">−0.00291 (5)</td><td rowspan="1" colspan="1">−0.00378 (6)</td><td rowspan="1" colspan="1">−0.00904 (6)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.0114 (7)</td><td rowspan="1" colspan="1">0.0402 (10)</td><td rowspan="1" colspan="1">0.0194 (8)</td><td rowspan="1" colspan="1">−0.0006 (7)</td><td rowspan="1" colspan="1">−0.0035 (6)</td><td rowspan="1" colspan="1">−0.0126 (7)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.0106 (8)</td><td rowspan="1" colspan="1">0.0271 (10)</td><td rowspan="1" colspan="1">0.0150 (9)</td><td rowspan="1" colspan="1">0.0003 (7)</td><td rowspan="1" colspan="1">−0.0026 (7)</td><td rowspan="1" colspan="1">−0.0103 (8)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.0134 (10)</td><td rowspan="1" colspan="1">0.0183 (10)</td><td rowspan="1" colspan="1">0.0171 (10)</td><td rowspan="1" colspan="1">−0.0018 (8)</td><td rowspan="1" colspan="1">−0.0013 (8)</td><td rowspan="1" colspan="1">−0.0078 (8)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.0118 (9)</td><td rowspan="1" colspan="1">0.0171 (10)</td><td rowspan="1" colspan="1">0.0169 (10)</td><td rowspan="1" colspan="1">0.0039 (8)</td><td rowspan="1" colspan="1">−0.0035 (8)</td><td rowspan="1" colspan="1">−0.0084 (8)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.0109 (9)</td><td rowspan="1" colspan="1">0.0172 (10)</td><td rowspan="1" colspan="1">0.0214 (11)</td><td rowspan="1" colspan="1">0.0004 (8)</td><td rowspan="1" colspan="1">−0.0028 (8)</td><td rowspan="1" colspan="1">−0.0105 (9)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0178 (10)</td><td rowspan="1" colspan="1">0.0221 (11)</td><td rowspan="1" colspan="1">0.0160 (10)</td><td rowspan="1" colspan="1">0.0002 (8)</td><td rowspan="1" colspan="1">0.0004 (8)</td><td rowspan="1" colspan="1">−0.0069 (9)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0207 (11)</td><td rowspan="1" colspan="1">0.0270 (12)</td><td rowspan="1" colspan="1">0.0174 (10)</td><td rowspan="1" colspan="1">0.0026 (9)</td><td rowspan="1" colspan="1">−0.0042 (8)</td><td rowspan="1" colspan="1">−0.0124 (9)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.0186 (10)</td><td rowspan="1" colspan="1">0.0216 (11)</td><td rowspan="1" colspan="1">0.0235 (11)</td><td rowspan="1" colspan="1">0.0002 (8)</td><td rowspan="1" colspan="1">−0.0063 (9)</td><td rowspan="1" colspan="1">−0.0124 (9)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.0131 (10)</td><td rowspan="1" colspan="1">0.0180 (10)</td><td rowspan="1" colspan="1">0.0187 (10)</td><td rowspan="1" colspan="1">−0.0005 (8)</td><td rowspan="1" colspan="1">−0.0013 (8)</td><td rowspan="1" colspan="1">−0.0070 (9)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.0129 (9)</td><td rowspan="1" colspan="1">0.0206 (10)</td><td rowspan="1" colspan="1">0.0161 (10)</td><td rowspan="1" colspan="1">−0.0047 (8)</td><td rowspan="1" colspan="1">−0.0003 (8)</td><td rowspan="1" colspan="1">−0.0095 (9)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.0139 (10)</td><td rowspan="1" colspan="1">0.0213 (11)</td><td rowspan="1" colspan="1">0.0203 (11)</td><td rowspan="1" colspan="1">−0.0010 (8)</td><td rowspan="1" colspan="1">−0.0018 (8)</td><td rowspan="1" colspan="1">−0.0103 (9)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.0179 (10)</td><td rowspan="1" colspan="1">0.0220 (11)</td><td rowspan="1" colspan="1">0.0179 (10)</td><td rowspan="1" colspan="1">−0.0045 (8)</td><td rowspan="1" colspan="1">−0.0046 (8)</td><td rowspan="1" colspan="1">−0.0071 (9)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.0208 (11)</td><td rowspan="1" colspan="1">0.0247 (11)</td><td rowspan="1" colspan="1">0.0182 (10)</td><td rowspan="1" colspan="1">−0.0076 (9)</td><td rowspan="1" colspan="1">0.0010 (8)</td><td rowspan="1" colspan="1">−0.0121 (9)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.0152 (10)</td><td rowspan="1" colspan="1">0.0256 (12)</td><td rowspan="1" colspan="1">0.0259 (12)</td><td rowspan="1" colspan="1">−0.0031 (9)</td><td rowspan="1" colspan="1">0.0014 (9)</td><td rowspan="1" colspan="1">−0.0159 (10)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.0138 (10)</td><td rowspan="1" colspan="1">0.0244 (11)</td><td rowspan="1" colspan="1">0.0218 (11)</td><td rowspan="1" colspan="1">0.0004 (8)</td><td rowspan="1" colspan="1">−0.0046 (8)</td><td rowspan="1" colspan="1">−0.0109 (9)</td></tr></table></table-wrap></sec><sec id="d1e2608" sec-type="tablewrapgeomlong"><label>2-Iodo-<italic>N</italic>-phenylbenzamide (II) </label><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e2618"><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">I1—C3</td><td rowspan="1" colspan="1">2.104 (2)</td><td rowspan="1" colspan="1">C6—H6</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">O1—C1</td><td rowspan="1" colspan="1">1.225 (3)</td><td rowspan="1" colspan="1">C7—H7</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">N1—C1</td><td rowspan="1" colspan="1">1.354 (3)</td><td rowspan="1" colspan="1">C8—C13</td><td rowspan="1" colspan="1">1.392 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—C8</td><td rowspan="1" colspan="1">1.420 (3)</td><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.394 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—H1</td><td rowspan="1" colspan="1">0.8800</td><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.388 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.505 (3)</td><td rowspan="1" colspan="1">C9—H9</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C2—C7</td><td rowspan="1" colspan="1">1.395 (3)</td><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.388 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.399 (3)</td><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.387 (3)</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.388 (3)</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.390 (3)</td><td rowspan="1" colspan="1">C11—H11</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C4—H4</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.382 (3)</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.385 (3)</td><td rowspan="1" colspan="1">C12—H12</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C6—C7</td><td rowspan="1" colspan="1">1.384 (3)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1—N1—C8</td><td rowspan="1" colspan="1">126.37 (18)</td><td rowspan="1" colspan="1">C6—C7—C2</td><td rowspan="1" colspan="1">120.8 (2)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—H1</td><td rowspan="1" colspan="1">116.8</td><td rowspan="1" colspan="1">C6—C7—H7</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">C8—N1—H1</td><td rowspan="1" colspan="1">116.8</td><td rowspan="1" colspan="1">C2—C7—H7</td><td rowspan="1" colspan="1">119.6</td></tr><tr><td rowspan="1" colspan="1">O1—C1—N1</td><td rowspan="1" colspan="1">124.4 (2)</td><td rowspan="1" colspan="1">C13—C8—C9</td><td rowspan="1" colspan="1">119.80 (19)</td></tr><tr><td rowspan="1" colspan="1">O1—C1—C2</td><td rowspan="1" colspan="1">121.64 (19)</td><td rowspan="1" colspan="1">C13—C8—N1</td><td rowspan="1" colspan="1">117.79 (19)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2</td><td rowspan="1" colspan="1">113.98 (18)</td><td rowspan="1" colspan="1">C9—C8—N1</td><td rowspan="1" colspan="1">122.38 (19)</td></tr><tr><td rowspan="1" colspan="1">C7—C2—C3</td><td rowspan="1" colspan="1">118.70 (19)</td><td rowspan="1" colspan="1">C10—C9—C8</td><td rowspan="1" colspan="1">119.4 (2)</td></tr><tr><td rowspan="1" colspan="1">C7—C2—C1</td><td rowspan="1" colspan="1">119.60 (19)</td><td rowspan="1" colspan="1">C10—C9—H9</td><td rowspan="1" colspan="1">120.3</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">121.68 (18)</td><td rowspan="1" colspan="1">C8—C9—H9</td><td rowspan="1" colspan="1">120.3</td></tr><tr><td rowspan="1" colspan="1">C4—C3—C2</td><td rowspan="1" colspan="1">120.61 (19)</td><td rowspan="1" colspan="1">C11—C10—C9</td><td rowspan="1" colspan="1">121.1 (2)</td></tr><tr><td rowspan="1" colspan="1">C4—C3—I1</td><td rowspan="1" colspan="1">117.07 (16)</td><td rowspan="1" colspan="1">C11—C10—H10</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">C2—C3—I1</td><td rowspan="1" colspan="1">122.08 (15)</td><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5</td><td rowspan="1" colspan="1">119.7 (2)</td><td rowspan="1" colspan="1">C10—C11—C12</td><td rowspan="1" colspan="1">119.0 (2)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—H4</td><td rowspan="1" colspan="1">120.1</td><td rowspan="1" colspan="1">C10—C11—H11</td><td rowspan="1" colspan="1">120.5</td></tr><tr><td rowspan="1" colspan="1">C5—C4—H4</td><td rowspan="1" colspan="1">120.1</td><td rowspan="1" colspan="1">C12—C11—H11</td><td rowspan="1" colspan="1">120.5</td></tr><tr><td rowspan="1" colspan="1">C6—C5—C4</td><td rowspan="1" colspan="1">120.3 (2)</td><td rowspan="1" colspan="1">C13—C12—C11</td><td rowspan="1" colspan="1">120.7 (2)</td></tr><tr><td rowspan="1" colspan="1">C6—C5—H5</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">C13—C12—H12</td><td rowspan="1" colspan="1">119.7</td></tr><tr><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">119.9</td><td rowspan="1" colspan="1">C11—C12—H12</td><td rowspan="1" colspan="1">119.7</td></tr><tr><td rowspan="1" colspan="1">C7—C6—C5</td><td rowspan="1" colspan="1">119.9 (2)</td><td rowspan="1" colspan="1">C12—C13—C8</td><td rowspan="1" colspan="1">120.1 (2)</td></tr><tr><td rowspan="1" colspan="1">C7—C6—H6</td><td rowspan="1" colspan="1">120.1</td><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">120.0</td></tr><tr><td rowspan="1" colspan="1">C5—C6—H6</td><td rowspan="1" colspan="1">120.1</td><td rowspan="1" colspan="1">C8—C13—H13</td><td rowspan="1" colspan="1">120.0</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">C8—N1—C1—O1</td><td rowspan="1" colspan="1">−0.6 (4)</td><td rowspan="1" colspan="1">C5—C6—C7—C2</td><td rowspan="1" colspan="1">0.6 (3)</td></tr><tr><td rowspan="1" colspan="1">C8—N1—C1—C2</td><td rowspan="1" colspan="1">179.69 (19)</td><td rowspan="1" colspan="1">C3—C2—C7—C6</td><td rowspan="1" colspan="1">−1.2 (3)</td></tr><tr><td rowspan="1" colspan="1">O1—C1—C2—C7</td><td rowspan="1" colspan="1">−127.2 (2)</td><td rowspan="1" colspan="1">C1—C2—C7—C6</td><td rowspan="1" colspan="1">177.16 (19)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2—C7</td><td rowspan="1" colspan="1">52.6 (3)</td><td rowspan="1" colspan="1">C1—N1—C8—C13</td><td rowspan="1" colspan="1">−152.1 (2)</td></tr><tr><td rowspan="1" colspan="1">O1—C1—C2—C3</td><td rowspan="1" colspan="1">51.1 (3)</td><td rowspan="1" colspan="1">C1—N1—C8—C9</td><td rowspan="1" colspan="1">29.9 (3)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2—C3</td><td rowspan="1" colspan="1">−129.1 (2)</td><td rowspan="1" colspan="1">C13—C8—C9—C10</td><td rowspan="1" colspan="1">−0.7 (3)</td></tr><tr><td rowspan="1" colspan="1">C7—C2—C3—C4</td><td rowspan="1" colspan="1">0.9 (3)</td><td rowspan="1" colspan="1">N1—C8—C9—C10</td><td rowspan="1" colspan="1">177.34 (19)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">−177.47 (19)</td><td rowspan="1" colspan="1">C8—C9—C10—C11</td><td rowspan="1" colspan="1">0.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C7—C2—C3—I1</td><td rowspan="1" colspan="1">−173.28 (15)</td><td rowspan="1" colspan="1">C9—C10—C11—C12</td><td rowspan="1" colspan="1">0.3 (3)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—I1</td><td rowspan="1" colspan="1">8.4 (3)</td><td rowspan="1" colspan="1">C10—C11—C12—C13</td><td rowspan="1" colspan="1">−0.1 (3)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">0.1 (3)</td><td rowspan="1" colspan="1">C11—C12—C13—C8</td><td rowspan="1" colspan="1">−0.4 (3)</td></tr><tr><td rowspan="1" colspan="1">I1—C3—C4—C5</td><td rowspan="1" colspan="1">174.51 (16)</td><td rowspan="1" colspan="1">C9—C8—C13—C12</td><td rowspan="1" colspan="1">0.8 (3)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td><td rowspan="1" colspan="1">−0.7 (3)</td><td rowspan="1" colspan="1">N1—C8—C13—C12</td><td rowspan="1" colspan="1">−177.3 (2)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—C7</td><td rowspan="1" colspan="1">0.4 (3)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="d1e3100" sec-type="tablewraphbondslong"><label>2-Iodo-<italic>N</italic>-phenylbenzamide (II) </label><title>Hydrogen-bond geometry (Å, º)</title><p>Cg2 is the centroid of the C8–C13 benzene ring.</p><table-wrap position="anchor" id="d1e3114"><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—H1···O1<sup>i</sup></td><td rowspan="1" colspan="1">0.88</td><td rowspan="1" colspan="1">2.15</td><td rowspan="1" colspan="1">2.942 (2)</td><td rowspan="1" colspan="1">150</td></tr><tr><td rowspan="1" colspan="1">C3—I1···<italic>Cg</italic>2<sup>ii</sup></td><td rowspan="1" colspan="1">2.10 (1)</td><td rowspan="1" colspan="1">3.83 (1)</td><td rowspan="1" colspan="1">5.816 (2)</td><td rowspan="1" colspan="1">156 (1)</td></tr><tr><td rowspan="1" colspan="1">C6—H6···<italic>Cg</italic>2<sup>iii</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.81</td><td rowspan="1" colspan="1">3.627 (2)</td><td rowspan="1" colspan="1">144</td></tr></table></table-wrap><p>Symmetry codes: (i) <italic>x</italic>+1, <italic>y</italic>, <italic>z</italic>; (ii) −<italic>x</italic>, −<italic>y</italic>, −<italic>z</italic>+1; (iii) −<italic>x</italic>+1, −<italic>y</italic>+1, −<italic>z</italic>+1.</p></sec></app></app-group><ref-list><title>References</title><ref 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(2005). <italic>Acta Cryst.</italic> C<bold>61</bold>, o634–o638.</mixed-citation></ref></ref-list></back><floats-group><fig id="fig1" orientation="portrait" position="float"><label>Figure 1</label><caption><p>The molecular structure of (I)<xref ref-type="chem" rid="scheme1"></xref> showing the atom numbering with ellipsoids drawn at the 50% probability level.</p></caption><graphic xlink:href="e-74-01130-fig1"></graphic></fig><fig id="fig2" orientation="portrait" position="float"><label>Figure 2</label><caption><p>The molecular structure of (II)<xref ref-type="chem" rid="scheme1"></xref> showing the atom numbering with ellipsoids drawn at the 50% probability level.</p></caption><graphic xlink:href="e-74-01130-fig2"></graphic></fig><fig id="fig3" orientation="portrait" position="float"><label>Figure 3</label><caption><p>Chains of molecules of (I)<xref ref-type="chem" rid="scheme1"></xref> along the <italic>a</italic>-axis direction, showing the dimers and tetramers formed by N—H⋯O hydrogen bonds.</p></caption><graphic xlink:href="e-74-01130-fig3"></graphic></fig><fig id="fig4" orientation="portrait" position="float"><label>Figure 4</label><caption><p>N—H⋯O and C—I⋯π(ring) contacts forming sheets of molecules of (I)<xref ref-type="chem" rid="scheme1"></xref> in the <italic>bc</italic> plane.</p></caption><graphic xlink:href="e-74-01130-fig4"></graphic></fig><fig id="fig5" orientation="portrait" position="float"><label>Figure 5</label><caption><p>N—H⋯O hydrogen bonds forming chains of molecules of (II)<xref ref-type="chem" rid="scheme1"></xref> along the <italic>a</italic>-axis direction.</p></caption><graphic xlink:href="e-74-01130-fig5"></graphic></fig><fig id="fig6" orientation="portrait" position="float"><label>Figure 6</label><caption><p>C—I⋯π(ring) and C—H⋯π(ring) contacts generating sheets of molecules of (II)<xref ref-type="chem" rid="scheme1"></xref> along the <italic>ab</italic> diagonal</p></caption><graphic xlink:href="e-74-01130-fig6"></graphic></fig><table-wrap id="table1" orientation="portrait" position="float"><label>Table 1</label><caption><title>Hydrogen-bond geometry (Å, °) for (I)<xref ref-type="chem" rid="scheme1"></xref></title><p><italic>Cg</italic>1 is the centroid of the C2–C7 phenyl ring.</p></caption><table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H</th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th></tr></thead><tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>A</italic>⋯O1<sup>i</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.86</td><td rowspan="1" colspan="1" align="left" valign="top">2.11</td><td rowspan="1" colspan="1" align="left" valign="top">2.951 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">164</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—H1<italic>B</italic>⋯O1<sup>ii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.86</td><td rowspan="1" colspan="1" align="left" valign="top">2.05</td><td rowspan="1" colspan="1" align="left" valign="top">2.843 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">154</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C3—I1⋯<italic>Cg</italic>1<sup>iii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">2.11 (1)</td><td rowspan="1" colspan="1" align="left" valign="top">3.99 (1)</td><td rowspan="1" colspan="1" align="left" valign="top">5.877 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">148 (1)</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-74-01130-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-74-01130-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iii) <inline-formula><inline-graphic xlink:href="e-74-01130-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap><table-wrap id="table2" orientation="portrait" position="float"><label>Table 2</label><caption><title>Hydrogen-bond geometry (Å, °) for (II)<xref ref-type="chem" rid="scheme1"></xref></title><p><italic>Cg</italic>2 is the centroid of the C8–C13 benzene ring.</p></caption><table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H</th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>⋯<italic>A</italic></th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>—H⋯<italic>A</italic></th></tr></thead><tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">N1—H1⋯O1<sup>i</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.88</td><td rowspan="1" colspan="1" align="left" valign="top">2.15</td><td rowspan="1" colspan="1" align="left" valign="top">2.942 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">150</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C3—I1⋯<italic>Cg</italic>2<sup>ii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">2.10 (1)</td><td rowspan="1" colspan="1" align="left" valign="top">3.83 (1)</td><td rowspan="1" colspan="1" align="left" valign="top">5.816 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">156 (1)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">C6—H6⋯<italic>Cg</italic>2<sup>iii</sup></td><td rowspan="1" colspan="1" align="left" valign="top">0.95</td><td rowspan="1" colspan="1" align="left" valign="top">2.81</td><td rowspan="1" colspan="1" align="left" valign="top">3.627 (2)</td><td rowspan="1" colspan="1" align="left" valign="top">144</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-74-01130-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-74-01130-efi7.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (iii) <inline-formula><inline-graphic xlink:href="e-74-01130-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap><table-wrap id="table3" orientation="portrait" position="float"><label>Table 3</label><caption><title>Experimental details</title></caption><table frame="hsides" rules="groups"><thead valign="top"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top"> </th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(I)</th><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(II)</th></tr></thead><tbody valign="top"><tr><td rowspan="1" colspan="3" align="left" valign="top">Crystal data</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Chemical formula</td><td rowspan="1" colspan="1" align="left" valign="top">C<sub>7</sub>H<sub>6</sub>INO</td><td rowspan="1" colspan="1" align="left" valign="top">C<sub>13</sub>H<sub>10</sub>INO</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>M</italic><sub>r</sub></td><td rowspan="1" colspan="1" align="left" valign="top">247.03</td><td rowspan="1" colspan="1" align="left" valign="top">323.12</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal system, space group</td><td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>2<sub>1</sub>/<italic>n</italic></td><td rowspan="1" colspan="1" align="left" valign="top">Triclinic, <italic>P</italic><inline-formula><inline-graphic xlink:href="e-74-01130-efi9.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula></td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Temperature (K)</td><td rowspan="1" colspan="1" align="left" valign="top">296</td><td rowspan="1" colspan="1" align="left" valign="top">120</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>a</italic>, <italic>b</italic>, <italic>c</italic> (Å)</td><td rowspan="1" colspan="1" align="left" valign="top">5.0531 (2), 11.4478 (5), 13.2945 (5)</td><td rowspan="1" colspan="1" align="left" valign="top">5.1225 (2), 10.4572 (4), 12.2167 (5)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">α, β, γ (°)</td><td rowspan="1" colspan="1" align="left" valign="top">90, 93.245 (1), 90</td><td rowspan="1" colspan="1" align="left" valign="top">66.034 (2), 78.882 (2), 85.760 (2)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>V</italic> (Å<sup>3</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">767.81 (5)</td><td rowspan="1" colspan="1" align="left" valign="top">586.76 (4)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>Z</italic></td><td rowspan="1" colspan="1" align="left" valign="top">4</td><td rowspan="1" colspan="1" align="left" valign="top">2</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Radiation type</td><td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>α</td><td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>α</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">μ (mm<sup>−1</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">4.10</td><td rowspan="1" colspan="1" align="left" valign="top">2.71</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal size (mm)</td><td rowspan="1" colspan="1" align="left" valign="top">0.23 × 0.22 × 0.21</td><td rowspan="1" colspan="1" align="left" valign="top">0.23 × 0.22 × 0.21</td></tr><tr><td rowspan="1" colspan="3" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="3" align="left" valign="top">Data collection</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Diffractometer</td><td rowspan="1" colspan="1" align="left" valign="top">Bruker Kappa APEXII DUO</td><td rowspan="1" colspan="1" align="left" valign="top">Bruker Kappa APEXII DUO</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Absorption correction</td><td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>SADABS</italic>; Bruker, 2014<xref ref-type="bibr" rid="bb2"> ▸</xref>)</td><td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>SADABS</italic>; Bruker, 2014<xref ref-type="bibr" rid="bb2"> ▸</xref>)</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>T</italic><sub>min</sub>, <italic>T</italic><sub>max</sub></td><td rowspan="1" colspan="1" align="left" valign="top">0.429, 0.456</td><td rowspan="1" colspan="1" align="left" valign="top">0.546, 0.570</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">No. of measured, independent and observed [<italic>I</italic> > 2σ(<italic>I</italic>)] reflections</td><td rowspan="1" colspan="1" align="left" valign="top">5827, 1504, 1461</td><td rowspan="1" colspan="1" align="left" valign="top">13292, 2309, 2278</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic><sub>int</sub></td><td rowspan="1" colspan="1" align="left" valign="top">0.021</td><td rowspan="1" colspan="1" align="left" valign="top">0.018</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">(sin θ/λ)<sub>max</sub> (Å<sup>−1</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">0.617</td><td rowspan="1" colspan="1" align="left" valign="top">0.617</td></tr><tr><td rowspan="1" colspan="3" align="left" valign="top"> </td></tr><tr><td rowspan="1" colspan="3" align="left" valign="top">Refinement</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)], <italic>wR</italic>(<italic>F</italic><sup>2</sup>), <italic>S</italic></td><td rowspan="1" colspan="1" align="left" valign="top">0.014, 0.033, 1.16</td><td rowspan="1" colspan="1" align="left" valign="top">0.017, 0.042, 1.08</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">No. of reflections</td><td rowspan="1" colspan="1" align="left" valign="top">1504</td><td rowspan="1" colspan="1" align="left" valign="top">2309</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">No. of parameters</td><td rowspan="1" colspan="1" align="left" valign="top">92</td><td rowspan="1" colspan="1" align="left" valign="top">145</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">H-atom treatment</td><td rowspan="1" colspan="1" align="left" valign="top">H-atom parameters constrained</td><td rowspan="1" colspan="1" align="left" valign="top">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1" align="left" valign="top">Δρ<sub>max</sub>, Δρ<sub>min</sub> (e Å<sup>−3</sup>)</td><td rowspan="1" colspan="1" align="left" valign="top">0.45, −0.35</td><td rowspan="1" colspan="1" align="left" valign="top">0.81, −0.48</td></tr></tbody></table><table-wrap-foot><p>Computer programs: <italic>APEX2</italic> and <italic>SAINT</italic> (Bruker, 2014<xref ref-type="bibr" rid="bb2"> ▸</xref>), <italic>SHELXS14</italic> (Sheldrick, 2008<xref ref-type="bibr" rid="bb18"> ▸</xref>), <italic>SHELXL2014</italic> (Sheldrick, 2015<xref ref-type="bibr" rid="bb19"> ▸</xref>), <italic>PLATON</italic> (Spek, 2009<xref ref-type="bibr" rid="bb20"> ▸</xref>), <italic>Mercury</italic> (Macrae <italic>et al.</italic>, 2008<xref ref-type="bibr" rid="bb11"> ▸</xref>), <italic>WinGX</italic> (Farrugia, 2012<xref ref-type="bibr" rid="bb4"> ▸</xref>) and <italic>PARST</italic> (Nardelli, 1995<xref ref-type="bibr" rid="bb14"> ▸</xref>).</p></table-wrap-foot></table-wrap></floats-group></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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