Crystal structure of (E)-N-{[3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methylidene}hydroxylamine
Identifieur interne : 001110 ( Pmc/Checkpoint ); précédent : 001109; suivant : 001111Crystal structure of (E)-N-{[3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methylidene}hydroxylamine
Auteurs : Joel T. Mague [États-Unis] ; Shaaban K. Mohamed [Égypte] ; Mehmet Akkurt [Turquie] ; Talaat I. El-Emary [Égypte] ; Mustafa R. Albayati [Iraq]Source :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2014.
Abstract
The title compound, C15H14N4O, crystallizes with two molecules in the asymmetric unit with similar conformations (r.m.s. overlay fit for the 20 non-H atoms = 0.175 Å). In the first molecule, the dihedral angles between the planes of the central pyrazole ring and the pendant phenyl and pyrrole rings are 42.69 (8) and 51.88 (6)°, respectively, with corresponding angles of 54.49 (7) and 49.61 (9)°, respectively, in the second molecule. In the crystal, the two molecules, together with their inversion-symmetry counterparts, are linked into tetramers by O—H⋯N hydrogen bonds. The tetramers form layers parallel to (211) through pairwise C—H⋯π interactions.
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DOI: 10.1107/S1600536814023514
PubMed: 25484837
PubMed Central: 4257281
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Crystal structure of (<italic>E</italic>)-<italic>N</italic>-{[3-methyl-1-phenyl-5-(1<italic>H</italic>-pyrrol-1-yl)-1<italic>H</italic>-pyrazol-4-yl]methylidene}hydroxylamine</title><author><name sortKey="Mague, Joel T" sort="Mague, Joel T" uniqKey="Mague J" first="Joel T." last="Mague">Joel T. Mague</name><affiliation wicri:level="1"><nlm:aff id="a">Department of Chemistry, Tulane University, New Orleans, LA 70118,<country>USA</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Mohamed, Shaaban K" sort="Mohamed, Shaaban K" uniqKey="Mohamed S" first="Shaaban K." last="Mohamed">Shaaban K. Mohamed</name><affiliation><nlm:aff id="b">Chemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD,<country>England</country></nlm:aff><wicri:noCountry code="nlm country">England</wicri:noCountry></affiliation><affiliation wicri:level="1"><nlm:aff id="c">Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia,<country>Egypt</country></nlm:aff><country xml:lang="fr">Égypte</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Akkurt, Mehmet" sort="Akkurt, Mehmet" uniqKey="Akkurt M" first="Mehmet" last="Akkurt">Mehmet Akkurt</name><affiliation wicri:level="1"><nlm:aff id="d">Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri,<country>Turkey</country></nlm:aff><country xml:lang="fr">Turquie</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="El Emary, Talaat I" sort="El Emary, Talaat I" uniqKey="El Emary T" first="Talaat I." last="El-Emary">Talaat I. El-Emary</name><affiliation wicri:level="1"><nlm:aff id="e">Department of Chemistry, Faculty of Science, Assiut University, 71515 Assiut,<country>Egypt</country></nlm:aff><country xml:lang="fr">Égypte</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Albayati, Mustafa R" sort="Albayati, Mustafa R" uniqKey="Albayati M" first="Mustafa R." last="Albayati">Mustafa R. Albayati</name><affiliation wicri:level="1"><nlm:aff id="f">Kirkuk University, College of Science, Department of Chemistry, Kirkuk,<country>Iraq</country></nlm:aff><country xml:lang="fr">Iraq</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">25484837</idno><idno type="pmc">4257281</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257281</idno><idno type="RBID">PMC:4257281</idno><idno type="doi">10.1107/S1600536814023514</idno><date when="2014">2014</date><idno type="wicri:Area/Pmc/Corpus">000997</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000997</idno><idno type="wicri:Area/Pmc/Curation">000997</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000997</idno><idno type="wicri:Area/Pmc/Checkpoint">001110</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">001110</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Crystal structure of (<italic>E</italic>)-<italic>N</italic>-{[3-methyl-1-phenyl-5-(1<italic>H</italic>-pyrrol-1-yl)-1<italic>H</italic>-pyrazol-4-yl]methylidene}hydroxylamine</title><author><name sortKey="Mague, Joel T" sort="Mague, Joel T" uniqKey="Mague J" first="Joel T." last="Mague">Joel T. Mague</name><affiliation wicri:level="1"><nlm:aff id="a">Department of Chemistry, Tulane University, New Orleans, LA 70118,<country>USA</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Mohamed, Shaaban K" sort="Mohamed, Shaaban K" uniqKey="Mohamed S" first="Shaaban K." last="Mohamed">Shaaban K. Mohamed</name><affiliation><nlm:aff id="b">Chemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD,<country>England</country></nlm:aff><wicri:noCountry code="nlm country">England</wicri:noCountry></affiliation><affiliation wicri:level="1"><nlm:aff id="c">Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia,<country>Egypt</country></nlm:aff><country xml:lang="fr">Égypte</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Akkurt, Mehmet" sort="Akkurt, Mehmet" uniqKey="Akkurt M" first="Mehmet" last="Akkurt">Mehmet Akkurt</name><affiliation wicri:level="1"><nlm:aff id="d">Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri,<country>Turkey</country></nlm:aff><country xml:lang="fr">Turquie</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="El Emary, Talaat I" sort="El Emary, Talaat I" uniqKey="El Emary T" first="Talaat I." last="El-Emary">Talaat I. El-Emary</name><affiliation wicri:level="1"><nlm:aff id="e">Department of Chemistry, Faculty of Science, Assiut University, 71515 Assiut,<country>Egypt</country></nlm:aff><country xml:lang="fr">Égypte</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Albayati, Mustafa R" sort="Albayati, Mustafa R" uniqKey="Albayati M" first="Mustafa R." last="Albayati">Mustafa R. Albayati</name><affiliation wicri:level="1"><nlm:aff id="f">Kirkuk University, College of Science, Department of Chemistry, Kirkuk,<country>Iraq</country></nlm:aff><country xml:lang="fr">Iraq</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></analytic><series><title level="j">Acta Crystallographica Section E: Structure Reports Online</title><idno type="eISSN">1600-5368</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The title compound, C<sub>15</sub>H<sub>14</sub>N<sub>4</sub>O, crystallizes with two molecules in the asymmetric unit with similar conformations (r.m.s. overlay fit for the 20 non-H atoms = 0.175 Å). In the first molecule, the dihedral angles between the planes of the central pyrazole ring and the pendant phenyl and pyrrole rings are 42.69 (8) and 51.88 (6)°, respectively, with corresponding angles of 54.49 (7) and 49.61 (9)°, respectively, in the second molecule. In the crystal, the two molecules, together with their inversion-symmetry counterparts, are linked into tetramers by O—H⋯N hydrogen bonds. The tetramers form layers parallel to (211) through pairwise C—H⋯π interactions.</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></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="iso-abbrev">Acta Crystallogr Sect E Struct Rep Online</journal-id><journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id><journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title></journal-title-group><issn pub-type="epub">1600-5368</issn><publisher><publisher-name>International Union of Crystallography</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">25484837</article-id><article-id pub-id-type="pmc">4257281</article-id><article-id pub-id-type="publisher-id">hb7307</article-id><article-id pub-id-type="doi">10.1107/S1600536814023514</article-id><article-id pub-id-type="coden">ACSEBH</article-id><article-id pub-id-type="pii">S1600536814023514</article-id><article-categories><subj-group subj-group-type="heading"><subject>Data Reports</subject></subj-group></article-categories><title-group><article-title>Crystal structure of (<italic>E</italic>)-<italic>N</italic>-{[3-methyl-1-phenyl-5-(1<italic>H</italic>-pyrrol-1-yl)-1<italic>H</italic>-pyrazol-4-yl]methylidene}hydroxylamine</article-title><alt-title><italic>C<sub>15</sub>H<sub>14</sub>N<sub>4</sub>O</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Mague</surname><given-names>Joel T.</given-names></name><xref ref-type="aff" rid="a">a</xref></contrib><contrib contrib-type="author"><name><surname>Mohamed</surname><given-names>Shaaban K.</given-names></name><xref ref-type="aff" rid="b">b</xref><xref ref-type="aff" rid="c">c</xref></contrib><contrib contrib-type="author"><name><surname>Akkurt</surname><given-names>Mehmet</given-names></name><xref ref-type="aff" rid="d">d</xref></contrib><contrib contrib-type="author"><name><surname>El-Emary</surname><given-names>Talaat I.</given-names></name><xref ref-type="aff" rid="e">e</xref></contrib><contrib contrib-type="author"><name><surname>Albayati</surname><given-names>Mustafa R.</given-names></name><xref ref-type="aff" rid="f">f</xref><xref ref-type="corresp" rid="cor">*</xref></contrib><aff id="a"><label>a</label>Department of Chemistry, Tulane University, New Orleans, LA 70118,<country>USA</country></aff><aff id="b"><label>b</label>Chemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD,<country>England</country></aff><aff id="c"><label>c</label>Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia,<country>Egypt</country></aff><aff id="d"><label>d</label>Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri,<country>Turkey</country></aff><aff id="e"><label>e</label>Department of Chemistry, Faculty of Science, Assiut University, 71515 Assiut,<country>Egypt</country></aff><aff id="f"><label>f</label>Kirkuk University, College of Science, Department of Chemistry, Kirkuk,<country>Iraq</country></aff></contrib-group><author-notes><corresp id="cor">Correspondence e-mail: <email>shaabankamel@yahoo.com</email></corresp></author-notes><pub-date pub-type="collection"><day>01</day><month>11</month><year>2014</year></pub-date><pub-date pub-type="epub"><day>31</day><month>10</month><year>2014</year></pub-date><pub-date pub-type="pmc-release"><day>31</day><month>10</month><year>2014</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
<volume>70</volume><issue>Pt 11</issue><issue-id pub-id-type="publisher-id">e141100</issue-id><fpage>o1216</fpage><lpage>o1217</lpage><history><date date-type="received"><day>25</day><month>10</month><year>2014</year></date><date date-type="accepted"><day>25</day><month>10</month><year>2014</year></date></history><permissions><copyright-statement>© Mague et al. 2014</copyright-statement><copyright-year>2014</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/S1600536814023514">A full version of this article is available from Crystallography Journals Online.</self-uri><abstract><p>The title compound, C<sub>15</sub>H<sub>14</sub>N<sub>4</sub>O, crystallizes with two molecules in the asymmetric unit with similar conformations (r.m.s. overlay fit for the 20 non-H atoms = 0.175 Å). In the first molecule, the dihedral angles between the planes of the central pyrazole ring and the pendant phenyl and pyrrole rings are 42.69 (8) and 51.88 (6)°, respectively, with corresponding angles of 54.49 (7) and 49.61 (9)°, respectively, in the second molecule. In the crystal, the two molecules, together with their inversion-symmetry counterparts, are linked into tetramers by O—H⋯N hydrogen bonds. The tetramers form layers parallel to (211) through pairwise C—H⋯π interactions.</p></abstract><kwd-group><kwd>crystal structure</kwd><kwd>pyrrole ring</kwd><kwd>hydrogen bonding</kwd><kwd>hydroxylamine</kwd></kwd-group></article-meta></front><floats-group><table-wrap id="table1" position="float"><label>Table 1</label><caption><title>Hydrogen-bond geometry (, )</title><p><italic>Cg</italic> is centroid of C1C6 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 style="" rowspan="1" colspan="1" align="left" valign="top">O2H2<italic>A</italic>N2<sup>i</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.84</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.95</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.7835(19)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">174</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O1H1<italic>A</italic>N6<sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.84</td><td style="" rowspan="1" colspan="1" align="left" valign="top">1.99</td><td style="" rowspan="1" colspan="1" align="left" valign="top">2.8277(19)</td><td style="" rowspan="1" colspan="1" align="left" valign="top">172</td></tr><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C11H11<italic>Cg</italic><sup>ii</sup></td><td style="" rowspan="1" colspan="1" align="left" valign="top">0.95</td><td style="" rowspan="1" colspan="1" align="left" valign="top">3.45</td><td style="" rowspan="1" colspan="1" align="left" valign="top">?</td><td style="" rowspan="1" colspan="1" align="left" valign="top">170</td></tr></tbody></table><table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-70-o1216-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>; (ii) <inline-formula><inline-graphic xlink:href="e-70-o1216-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>.</p></table-wrap-foot></table-wrap></floats-group></pmc><affiliations><list><country><li>Iraq</li><li>Turquie</li><li>Égypte</li><li>États-Unis</li></country></list><tree><country name="États-Unis"><noRegion><name sortKey="Mague, Joel T" sort="Mague, Joel T" uniqKey="Mague J" first="Joel T." last="Mague">Joel T. Mague</name></noRegion></country><country name="Égypte"><noRegion><name sortKey="Mohamed, Shaaban K" sort="Mohamed, Shaaban K" uniqKey="Mohamed S" first="Shaaban K." last="Mohamed">Shaaban K. Mohamed</name></noRegion><name sortKey="El Emary, Talaat I" sort="El Emary, Talaat I" uniqKey="El Emary T" first="Talaat I." last="El-Emary">Talaat I. El-Emary</name></country><country name="Turquie"><noRegion><name sortKey="Akkurt, Mehmet" sort="Akkurt, Mehmet" uniqKey="Akkurt M" first="Mehmet" last="Akkurt">Mehmet Akkurt</name></noRegion></country><country name="Iraq"><noRegion><name sortKey="Albayati, Mustafa R" sort="Albayati, Mustafa R" uniqKey="Albayati M" first="Mustafa R." last="Albayati">Mustafa R. Albayati</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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