A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine.
Identifieur interne : 001E39 ( PubMed/Corpus ); précédent : 001E38; suivant : 001E40A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine.
Auteurs : Kurt MereiterSource :
- Acta crystallographica. Section E, Structure reports online [ 1600-5368 ] ; 2011.
Abstract
The herbicide triflusulfuron-methyl (systematic name: methyl 2-{[4-dimethyl-amino-6-(2,2,2-trifluoro-eth-oxy)-1,3,5-triazin-2-yl]carbamoylsulfamo-yl}-3-methyl-benzoate) and its degradation product triazine amine [systematic name: 2-amino-4-dimethyl-amino-6-(2,2,2-trifluoro-eth-oxy)-1,3,5-triazine] form a triclinic 1:1 co-crystal of the title compound, C(7)H(10)F(3)N(5)O·C(17)H(19)F(3)N(6)O(6)S, in which its two components are connected via a pair of complementary N-H⋯N hydrogen bonds, similar to the monoclinic crystal structure of the parent compound triflusulfuron-methyl [Mereiter (2011 ▶). Acta Cryst. E67, o1778-o1779] in which a pair of mol-ecules related by a twofold axis are linked by two N-H⋯N bonds. The triflusulfuron-methyl mol-ecules of both crystal structures are similar in geometric parameters and conformation, which is due to stiffening by a short intra-molecular N-H⋯N bond [N⋯N = 2.620 (4) Å] and an intra-molecular dipole-dipole inter-action between the sulfamide and the carboxyl moieties, with O(s)⋯C(c) = 2.802 (5) Å and O(c)⋯N(s) = 2.846 (4) Å. Inter-molecular N-H⋯O hydrogen bonds and slipped π-π stacking inter-actions between the diamino-triazine moieties [perpendicular distances of 3.25 Å within hydrogen-bonded tetra-mers and 3.27 Å between adjacent tetra-mers] link the two constituents of the co-crystal into columns parallel to the a axis. An intra-molecular C-H⋯O hydrogen bond occurs in the triflusulfuron-methyl mol-ecule and inter-molecular C-H⋯O inter-actions between triflusulfuron-methyl mol-ecules 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(3) group is partly orientationally disordered.
DOI: 10.1107/S1600536811031631
PubMed: 22058947
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<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><nlm:affiliation>Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria.</nlm:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2011">2011</date><idno type="RBID">pubmed:22058947</idno><idno type="pmid">22058947</idno><idno type="doi">10.1107/S1600536811031631</idno><idno type="wicri:Area/PubMed/Corpus">001E39</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001E39</idno></publicationStmt><sourceDesc><biblStruct><analytic><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><nlm:affiliation>Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria.</nlm:affiliation></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" type="published">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The herbicide triflusulfuron-methyl (systematic name: methyl 2-{[4-dimethyl-amino-6-(2,2,2-trifluoro-eth-oxy)-1,3,5-triazin-2-yl]carbamoylsulfamo-yl}-3-methyl-benzoate) and its degradation product triazine amine [systematic name: 2-amino-4-dimethyl-amino-6-(2,2,2-trifluoro-eth-oxy)-1,3,5-triazine] form a triclinic 1:1 co-crystal of the title compound, C(7)H(10)F(3)N(5)O·C(17)H(19)F(3)N(6)O(6)S, in which its two components are connected via a pair of complementary N-H⋯N hydrogen bonds, similar to the monoclinic crystal structure of the parent compound triflusulfuron-methyl [Mereiter (2011 ▶). Acta Cryst. E67, o1778-o1779] in which a pair of mol-ecules related by a twofold axis are linked by two N-H⋯N bonds. The triflusulfuron-methyl mol-ecules of both crystal structures are similar in geometric parameters and conformation, which is due to stiffening by a short intra-molecular N-H⋯N bond [N⋯N = 2.620 (4) Å] and an intra-molecular dipole-dipole inter-action between the sulfamide and the carboxyl moieties, with O(s)⋯C(c) = 2.802 (5) Å and O(c)⋯N(s) = 2.846 (4) Å. Inter-molecular N-H⋯O hydrogen bonds and slipped π-π stacking inter-actions between the diamino-triazine moieties [perpendicular distances of 3.25 Å within hydrogen-bonded tetra-mers and 3.27 Å between adjacent tetra-mers] link the two constituents of the co-crystal into columns parallel to the a axis. An intra-molecular C-H⋯O hydrogen bond occurs in the triflusulfuron-methyl mol-ecule and inter-molecular C-H⋯O inter-actions between triflusulfuron-methyl mol-ecules 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(3) group is partly orientationally disordered.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">22058947</PMID><DateCompleted><Year>2011</Year><Month>11</Month><Day>10</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1600-5368</ISSN><JournalIssue CitedMedium="Internet"><Volume>67</Volume><Issue>Pt 9</Issue><PubDate><Year>2011</Year><Month>Sep</Month><Day>01</Day></PubDate></JournalIssue><Title>Acta crystallographica. Section E, Structure reports online</Title><ISOAbbreviation>Acta Crystallogr Sect E Struct Rep Online</ISOAbbreviation></Journal><ArticleTitle>A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine.</ArticleTitle><Pagination><MedlinePgn>o2321-2</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1107/S1600536811031631</ELocationID><Abstract><AbstractText>The herbicide triflusulfuron-methyl (systematic name: methyl 2-{[4-dimethyl-amino-6-(2,2,2-trifluoro-eth-oxy)-1,3,5-triazin-2-yl]carbamoylsulfamo-yl}-3-methyl-benzoate) and its degradation product triazine amine [systematic name: 2-amino-4-dimethyl-amino-6-(2,2,2-trifluoro-eth-oxy)-1,3,5-triazine] form a triclinic 1:1 co-crystal of the title compound, C(7)H(10)F(3)N(5)O·C(17)H(19)F(3)N(6)O(6)S, in which its two components are connected via a pair of complementary N-H⋯N hydrogen bonds, similar to the monoclinic crystal structure of the parent compound triflusulfuron-methyl [Mereiter (2011 ▶). Acta Cryst. E67, o1778-o1779] in which a pair of mol-ecules related by a twofold axis are linked by two N-H⋯N bonds. The triflusulfuron-methyl mol-ecules of both crystal structures are similar in geometric parameters and conformation, which is due to stiffening by a short intra-molecular N-H⋯N bond [N⋯N = 2.620 (4) Å] and an intra-molecular dipole-dipole inter-action between the sulfamide and the carboxyl moieties, with O(s)⋯C(c) = 2.802 (5) Å and O(c)⋯N(s) = 2.846 (4) Å. Inter-molecular N-H⋯O hydrogen bonds and slipped π-π stacking inter-actions between the diamino-triazine moieties [perpendicular distances of 3.25 Å within hydrogen-bonded tetra-mers and 3.27 Å between adjacent tetra-mers] link the two constituents of the co-crystal into columns parallel to the a axis. An intra-molecular C-H⋯O hydrogen bond occurs in the triflusulfuron-methyl mol-ecule and inter-molecular C-H⋯O inter-actions between triflusulfuron-methyl mol-ecules 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(3) group is partly orientationally disordered.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Mereiter</LastName><ForeName>Kurt</ForeName><Initials>K</Initials><AffiliationInfo><Affiliation>Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2011</Year><Month>08</Month><Day>11</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Acta Crystallogr Sect E Struct Rep Online</MedlineTA><NlmUniqueID>101089178</NlmUniqueID><ISSNLinking>1600-5368</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2011</Year><Month>07</Month><Day>05</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2011</Year><Month>08</Month><Day>04</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2011</Year><Month>11</Month><Day>8</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2011</Year><Month>11</Month><Day>8</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2011</Year><Month>11</Month><Day>8</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">22058947</ArticleId><ArticleId IdType="doi">10.1107/S1600536811031631</ArticleId><ArticleId IdType="pii">pk2336</ArticleId><ArticleId IdType="pmc">PMC3200658</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22</Citation><ArticleIdList><ArticleId IdType="pubmed">18156677</ArticleId></ArticleIdList></Reference><Reference><Citation>Acta Crystallogr Sect E Struct Rep Online. 2011 Jul 1;67(Pt 7):o1778-9</Citation><ArticleIdList><ArticleId IdType="pubmed">21837154</ArticleId></ArticleIdList></Reference><Reference><Citation>Acta Crystallogr D Biol Crystallogr. 2009 Feb;65(Pt 2):148-55</Citation><ArticleIdList><ArticleId IdType="pubmed">19171970</ArticleId></ArticleIdList></Reference></ReferenceList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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