Methyl N-(3-cyanopicolinoyl)-l-tryptophanate
Identifieur interne : 000174 ( Pmc/Curation ); précédent : 000173; suivant : 000175Methyl N-(3-cyanopicolinoyl)-l-tryptophanate
Auteurs : Olga Ovdiichuk [Ukraine] ; Olga Hordiyenko [Ukraine] ; Zoia Voitenko [Ukraine] ; Axelle Arrault [France] ; Volodymyr Medviediev [Ukraine]Source :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2013.
Abstract
In the title compound, C19H16N4O3, the stereocenter has an
Url:
DOI: 10.1107/S160053681303153X
PubMed: 24454241
PubMed Central: 3885065
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Methyl <italic>N</italic>
-(3-cyanopicolinoyl)-<sc>l</sc>
-tryptophanate</title>
<author><name sortKey="Ovdiichuk, Olga" sort="Ovdiichuk, Olga" uniqKey="Ovdiichuk O" first="Olga" last="Ovdiichuk">Olga Ovdiichuk</name>
<affiliation wicri:level="1"><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country>
</nlm:aff>
<country xml:lang="fr">Ukraine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Hordiyenko, Olga" sort="Hordiyenko, Olga" uniqKey="Hordiyenko O" first="Olga" last="Hordiyenko">Olga Hordiyenko</name>
<affiliation wicri:level="1"><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country>
</nlm:aff>
<country xml:lang="fr">Ukraine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Voitenko, Zoia" sort="Voitenko, Zoia" uniqKey="Voitenko Z" first="Zoia" last="Voitenko">Zoia Voitenko</name>
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<author><name sortKey="Arrault, Axelle" sort="Arrault, Axelle" uniqKey="Arrault A" first="Axelle" last="Arrault">Axelle Arrault</name>
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</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Medviediev, Volodymyr" sort="Medviediev, Volodymyr" uniqKey="Medviediev V" first="Volodymyr" last="Medviediev">Volodymyr Medviediev</name>
<affiliation wicri:level="1"><nlm:aff id="c">STC "Institute for Single Crystals", National Academy of Science of Ukraine, Lenina ave. 60, 61001, Khar’kov,<country>Ukraine</country>
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<country xml:lang="fr">Ukraine</country>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Methyl <italic>N</italic>
-(3-cyanopicolinoyl)-<sc>l</sc>
-tryptophanate</title>
<author><name sortKey="Ovdiichuk, Olga" sort="Ovdiichuk, Olga" uniqKey="Ovdiichuk O" first="Olga" last="Ovdiichuk">Olga Ovdiichuk</name>
<affiliation wicri:level="1"><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country>
</nlm:aff>
<country xml:lang="fr">Ukraine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Hordiyenko, Olga" sort="Hordiyenko, Olga" uniqKey="Hordiyenko O" first="Olga" last="Hordiyenko">Olga Hordiyenko</name>
<affiliation wicri:level="1"><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country>
</nlm:aff>
<country xml:lang="fr">Ukraine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Voitenko, Zoia" sort="Voitenko, Zoia" uniqKey="Voitenko Z" first="Zoia" last="Voitenko">Zoia Voitenko</name>
<affiliation wicri:level="1"><nlm:aff id="a">Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country>
</nlm:aff>
<country xml:lang="fr">Ukraine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Arrault, Axelle" sort="Arrault, Axelle" uniqKey="Arrault A" first="Axelle" last="Arrault">Axelle Arrault</name>
<affiliation wicri:level="1"><nlm:aff id="b">Laboratoire de Chimie Physique Macromoleculaire, UMR 7568, ENSIC, BP 451, 54001 Nancy,<country>France</country>
</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Medviediev, Volodymyr" sort="Medviediev, Volodymyr" uniqKey="Medviediev V" first="Volodymyr" last="Medviediev">Volodymyr Medviediev</name>
<affiliation wicri:level="1"><nlm:aff id="c">STC "Institute for Single Crystals", National Academy of Science of Ukraine, Lenina ave. 60, 61001, Khar’kov,<country>Ukraine</country>
</nlm:aff>
<country xml:lang="fr">Ukraine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<series><title level="j">Acta Crystallographica Section E: Structure Reports Online</title>
<idno type="eISSN">1600-5368</idno>
<imprint><date when="2013">2013</date>
</imprint>
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<front><div type="abstract" xml:lang="en"><p>In the title compound, C<sub>19</sub>
H<sub>16</sub>
N<sub>4</sub>
O<sub>3</sub>
, the stereocenter has an <sc>l</sc>
configuration; <sc>l</sc>
-tryptophan methyl ester hydrochloride being used as a starting material. The indole ring system and the pyridine ring are inclined to one another by 13.55 (14)°. In the crystal, adjacent molecules are linked <italic>via</italic>
N—H⋯O hydrogen bonds, forming chains propagating along the <italic>c</italic>
-axis direction.</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
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<biblStruct></biblStruct>
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<biblStruct></biblStruct>
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<biblStruct></biblStruct>
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<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">24454241</article-id>
<article-id pub-id-type="pmc">3885065</article-id>
<article-id pub-id-type="publisher-id">su2666</article-id>
<article-id pub-id-type="doi">10.1107/S160053681303153X</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S160053681303153X</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject>
</subj-group>
</article-categories>
<title-group><article-title>Methyl <italic>N</italic>
-(3-cyanopicolinoyl)-<sc>l</sc>
-tryptophanate</article-title>
<alt-title><italic>C<sub>19</sub>
H<sub>16</sub>
N<sub>4</sub>
O<sub>3</sub>
</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Ovdiichuk</surname>
<given-names>Olga</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Hordiyenko</surname>
<given-names>Olga</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Voitenko</surname>
<given-names>Zoia</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Arrault</surname>
<given-names>Axelle</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Medviediev</surname>
<given-names>Volodymyr</given-names>
</name>
<xref ref-type="aff" rid="c">c</xref>
<xref ref-type="corresp" rid="cor">*</xref>
</contrib>
<aff id="a"><label>a</label>
Kyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv,<country>Ukraine</country>
</aff>
<aff id="b"><label>b</label>
Laboratoire de Chimie Physique Macromoleculaire, UMR 7568, ENSIC, BP 451, 54001 Nancy,<country>France</country>
</aff>
<aff id="c"><label>c</label>
STC "Institute for Single Crystals", National Academy of Science of Ukraine, Lenina ave. 60, 61001, Khar’kov,<country>Ukraine</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>vmedvedev@xray.isc.kharkov.com</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>12</month>
<year>2013</year>
</pub-date>
<pub-date pub-type="epub"><day>23</day>
<month>11</month>
<year>2013</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>23</day>
<month>11</month>
<year>2013</year>
</pub-date>
<volume>69</volume>
<issue>Pt 12</issue>
<issue-id pub-id-type="publisher-id">e131200</issue-id>
<fpage>o1810</fpage>
<lpage>o1810</lpage>
<history><date date-type="received"><day>13</day>
<month>11</month>
<year>2013</year>
</date>
<date date-type="accepted"><day>19</day>
<month>11</month>
<year>2013</year>
</date>
</history>
<permissions><copyright-statement>© Ovdiichuk et al. 2013</copyright-statement>
<copyright-year>2013</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/S160053681303153X">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract><p>In the title compound, C<sub>19</sub>
H<sub>16</sub>
N<sub>4</sub>
O<sub>3</sub>
, the stereocenter has an <sc>l</sc>
configuration; <sc>l</sc>
-tryptophan methyl ester hydrochloride being used as a starting material. The indole ring system and the pyridine ring are inclined to one another by 13.55 (14)°. In the crystal, adjacent molecules are linked <italic>via</italic>
N—H⋯O hydrogen bonds, forming chains propagating along the <italic>c</italic>
-axis direction.</p>
</abstract>
</article-meta>
</front>
<floats-group><table-wrap id="table1" position="float"><label>Table 1</label>
<caption><title>Hydrogen-bond geometry (Å, °)</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N4—H4⋯O1<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.86</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.29</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.987 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">138</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-69-o1810-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>
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