A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine
Identifieur interne : 001339 ( Pmc/Checkpoint ); précédent : 001338; suivant : 001340A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine
Auteurs : Kurt Mereiter [Autriche]Source :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2011.
Abstract
The herbicide triflusulfuron-methyl (systematic name: methyl 2-{[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoylsulfamoyl}-3-methylbenzoate) and its degradation product triazine amine [systematic name: 2-amino-4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine] form a triclinic 1:1 co-crystal of the title compound, C7H10F3N5O·C17H19F3N6O6S, in which its two components are connected
Url:
DOI: 10.1107/S1600536811031631
PubMed: 22058947
PubMed Central: 3200658
Affiliations:
Links toward previous steps (curation, corpus...)
Links to Exploration step
PMC:3200658Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine</title>
<author><name sortKey="Mereiter, Kurt" sort="Mereiter, Kurt" uniqKey="Mereiter K" first="Kurt" last="Mereiter">Kurt Mereiter</name>
<affiliation wicri:level="1"><nlm:aff id="a">Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna,<country>Austria</country>
</nlm:aff>
<country xml:lang="fr">Autriche</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PMC</idno>
<idno type="pmid">22058947</idno>
<idno type="pmc">3200658</idno>
<idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3200658</idno>
<idno type="RBID">PMC:3200658</idno>
<idno type="doi">10.1107/S1600536811031631</idno>
<date when="2011">2011</date>
<idno type="wicri:Area/Pmc/Corpus">000A23</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A23</idno>
<idno type="wicri:Area/Pmc/Curation">000A23</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000A23</idno>
<idno type="wicri:Area/Pmc/Checkpoint">001339</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">001339</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine</title>
<author><name sortKey="Mereiter, Kurt" sort="Mereiter, Kurt" uniqKey="Mereiter K" first="Kurt" last="Mereiter">Kurt Mereiter</name>
<affiliation wicri:level="1"><nlm:aff id="a">Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna,<country>Austria</country>
</nlm:aff>
<country xml:lang="fr">Autriche</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="2011">2011</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"><p>The herbicide triflusulfuron-methyl (systematic name: methyl 2-{[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoylsulfamoyl}-3-methylbenzoate) and its degradation product triazine amine [systematic name: 2-amino-4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine] form a triclinic 1:1 co-crystal of the title compound, C<sub>7</sub>
H<sub>10</sub>
F<sub>3</sub>
N<sub>5</sub>
O·C<sub>17</sub>
H<sub>19</sub>
F<sub>3</sub>
N<sub>6</sub>
O<sub>6</sub>
S, in which its two components are connected <italic>via</italic>
a pair of complementary N—H⋯N hydrogen bonds, similar to the monoclinic crystal structure of the parent compound triflusulfuron-methyl [Mereiter (2011<xref ref-type="bibr" rid="bb4"> ▶</xref>
). <italic>Acta Cryst.</italic>
E<bold>67</bold>
, o1778–o1779] in which a pair of molecules related by a twofold axis are linked by two N—H⋯N bonds. The triflusulfuron-methyl molecules of both crystal structures are similar in geometric parameters and conformation, which is due to stiffening by a short intramolecular N—H⋯N bond [N⋯N = 2.620 (4) Å] and an intramolecular dipole–dipole interaction between the sulfamide and the carboxyl moieties, with O<sub>s</sub>
⋯C<sub>c</sub>
= 2.802 (5) Å and O<sub>c</sub>
⋯N<sub>s</sub>
= 2.846 (4) Å. Intermolecular N—H⋯O hydrogen bonds and slipped π–π stacking interactions between the diaminotriazine moieties [perpendicular distances of 3.25 Å within hydrogen-bonded tetramers and 3.27 Å between adjacent tetramers] link the two constituents of the co-crystal into columns parallel to the <italic>a</italic>
axis. An intramolecular C—H⋯O hydrogen bond occurs in the triflusulfuron-methyl molecule and intermolecular C—H⋯O interactions between triflusulfuron-methyl molecules occur in the crystal structure. In the triflusulfuron-methyl molecule the dihedral angle between the least-squares planes of the two rings is 75.8 (1)°. In the triazine molecule, the CF<sub>3</sub>
group is partly orientationally disordered.</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
</listBibl>
</div1>
</back>
</TEI>
<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id>
<journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id>
<journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title>
</journal-title-group>
<issn pub-type="epub">1600-5368</issn>
<publisher><publisher-name>International Union of Crystallography</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">22058947</article-id>
<article-id pub-id-type="pmc">3200658</article-id>
<article-id pub-id-type="publisher-id">pk2336</article-id>
<article-id pub-id-type="doi">10.1107/S1600536811031631</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S1600536811031631</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject>
</subj-group>
</article-categories>
<title-group><article-title>A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine</article-title>
<alt-title><italic>C<sub>7</sub>
H<sub>10</sub>
F<sub>3</sub>
N<sub>5</sub>
O·C<sub>17</sub>
H<sub>19</sub>
F<sub>3</sub>
N<sub>6</sub>
O<sub>6</sub>
S</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Mereiter</surname>
<given-names>Kurt</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>
Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna,<country>Austria</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>kurt.mereiter@tuwien.ac.at</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>9</month>
<year>2011</year>
</pub-date>
<pub-date pub-type="epub"><day>11</day>
<month>8</month>
<year>2011</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>11</day>
<month>8</month>
<year>2011</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
. </pmc-comment>
<volume>67</volume>
<issue>Pt 9</issue>
<issue-id pub-id-type="publisher-id">e110900</issue-id>
<fpage>o2321</fpage>
<lpage>o2322</lpage>
<history><date date-type="received"><day>05</day>
<month>7</month>
<year>2011</year>
</date>
<date date-type="accepted"><day>04</day>
<month>8</month>
<year>2011</year>
</date>
</history>
<permissions><copyright-statement>© Kurt Mereiter 2011</copyright-statement>
<copyright-year>2011</copyright-year>
<license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/uk/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p>
</license>
</permissions>
<self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536811031631">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract><p>The herbicide triflusulfuron-methyl (systematic name: methyl 2-{[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoylsulfamoyl}-3-methylbenzoate) and its degradation product triazine amine [systematic name: 2-amino-4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine] form a triclinic 1:1 co-crystal of the title compound, C<sub>7</sub>
H<sub>10</sub>
F<sub>3</sub>
N<sub>5</sub>
O·C<sub>17</sub>
H<sub>19</sub>
F<sub>3</sub>
N<sub>6</sub>
O<sub>6</sub>
S, in which its two components are connected <italic>via</italic>
a pair of complementary N—H⋯N hydrogen bonds, similar to the monoclinic crystal structure of the parent compound triflusulfuron-methyl [Mereiter (2011<xref ref-type="bibr" rid="bb4"> ▶</xref>
). <italic>Acta Cryst.</italic>
E<bold>67</bold>
, o1778–o1779] in which a pair of molecules related by a twofold axis are linked by two N—H⋯N bonds. The triflusulfuron-methyl molecules of both crystal structures are similar in geometric parameters and conformation, which is due to stiffening by a short intramolecular N—H⋯N bond [N⋯N = 2.620 (4) Å] and an intramolecular dipole–dipole interaction between the sulfamide and the carboxyl moieties, with O<sub>s</sub>
⋯C<sub>c</sub>
= 2.802 (5) Å and O<sub>c</sub>
⋯N<sub>s</sub>
= 2.846 (4) Å. Intermolecular N—H⋯O hydrogen bonds and slipped π–π stacking interactions between the diaminotriazine moieties [perpendicular distances of 3.25 Å within hydrogen-bonded tetramers and 3.27 Å between adjacent tetramers] link the two constituents of the co-crystal into columns parallel to the <italic>a</italic>
axis. An intramolecular C—H⋯O hydrogen bond occurs in the triflusulfuron-methyl molecule and intermolecular C—H⋯O interactions between triflusulfuron-methyl molecules occur in the crystal structure. In the triflusulfuron-methyl molecule the dihedral angle between the least-squares planes of the two rings is 75.8 (1)°. In the triazine molecule, the CF<sub>3</sub>
group is partly orientationally disordered.</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">N1—H1<italic>N</italic>
⋯N5</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.88</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.94</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.620 (4)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">133</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N2—H2<italic>N</italic>
⋯N8</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.88</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.20</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.080 (4)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">176</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">N7—H7<italic>NA</italic>
⋯N3</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.88</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.11</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.989 (5)</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">N7—H7<italic>NB</italic>
⋯O3<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.88</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.13</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.996 (4)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">167</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C5—H5⋯O2<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">2.57</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.434 (5)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">152</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C8—H8<italic>A</italic>
⋯O2<sup>iii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.98</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.43</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.398 (5)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">170</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C9—H9<italic>A</italic>
⋯O5</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.98</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.40</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.210 (5)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">140</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">C16—H16<italic>B</italic>
⋯O5<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.99</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.47</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.373 (5)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">152</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-67-o2321-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-67-o2321-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (iii) <inline-formula><inline-graphic xlink:href="e-67-o2321-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
<affiliations><list><country><li>Autriche</li>
</country>
</list>
<tree><country name="Autriche"><noRegion><name sortKey="Mereiter, Kurt" sort="Mereiter, Kurt" uniqKey="Mereiter K" first="Kurt" last="Mereiter">Kurt Mereiter</name>
</noRegion>
</country>
</tree>
</affiliations>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/MersV1/Data/Pmc/Checkpoint
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 001339 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Pmc/Checkpoint/biblio.hfd -nk 001339 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Sante |area= MersV1 |flux= Pmc |étape= Checkpoint |type= RBID |clé= PMC:3200658 |texte= A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Pmc/Checkpoint/RBID.i -Sk "pubmed:22058947" \ | HfdSelect -Kh $EXPLOR_AREA/Data/Pmc/Checkpoint/biblio.hfd \ | NlmPubMed2Wicri -a MersV1
This area was generated with Dilib version V0.6.33. |