A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine

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Acta crystallographica.Section E, Structure reports online

Acta Crystallogr.Sect.E.Struct.Rep.Online

1-Sep

Pt 9

o2321

LR: 20130228; JID: 101089178; OID: NLM: PMC3200658; 2011/07/05 [received]; 2011/08/04 [accepted]; 2011/08/11 [epublish]; ppublish

England

1600-5368; 1600-5368

PMID: 22058947

eng

Journal Article

10.1107/S1600536811031631 [doi]

Unknown(0)

22058947

The herbicide triflusulfuron-methyl (systematic name: methyl 2-{[4-dimethyl-amino-6-(2,2,2-trifluoro-eth-oxy)-1,3,5-triazin-2-yl]carbamoylsulf amo-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-Hcdots, three dots, centeredN 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-Hcdots, three dots, centeredN 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-Hcdots, three dots, centeredN bond [Ncdots, three dots, centeredN = 2.620 (4) A] and an intra-molecular dipole-dipole inter-action between the sulfamide and the carboxyl moieties, with O(s)cdots, three dots, centeredC(c) = 2.802 (5) A and O(c)cdots, three dots, centeredN(s) = 2.846 (4) A. Inter-molecular N-Hcdots, three dots, centeredO hydrogen bonds and slipped pi-pi stacking inter-actions between the diamino-triazine moieties [perpendicular distances of 3.25 A within hydrogen-bonded tetra-mers and 3.27 A between adjacent tetra-mers] link the two constituents of the co-crystal into columns parallel to the a axis. An intra-molecular C-Hcdots, three dots, centeredO hydrogen bond occurs in the triflusulfuron-methyl mol-ecule and inter-molecular C-Hcdots, three dots, centeredO 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) degrees . In the triazine molecule, the CF(3) group is partly orientationally disordered.

Mereiter,K.

Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria.

20110811

PMC3200658

http://vp9py7xf3h.search.serialssolutions.com/?charset=utf-8&pmid=22058947

2011