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 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 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 Os⋯Cc = 2.802 (5) Å and Oc⋯Ns = 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 a 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 CF3 group is partly orientationally disordered.
Highlights
Acta Crystallographica Section E herbicidal properties of triflusulfuron-methyl, see: Moon (1989); Peeples et al (1991); Wittenbach et al (1994)
2-{[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2yl]carbamoylsulfamoyl}-3-methylbenzoate) and its degradation product triazine amine [systematic name: 2-amino-4dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine] form a triclinic 1:1 co-crystal of the title compound, C7H10F3N5OC17H19F3N6O6S, 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)
In case of the title compound the cocrystal formation is interesting, but is not desirable on following grounds: The triazine amine as one of the two components of the cocrystal of (I) has unwanted biocidal properties, and the cocrystal formation may probably impede the purification of triazine amine contaminated triflusulfuron-methyl by industrial batch crystallization
Summary
E67, 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 Os Cc = 2.802 (5) Å and Oc Ns = 2.846 (4) Å. Intermolecular N—H O hydrogen bonds and slipped – 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 a axis. H O interactions between triflusulfuron-methyl molecules occur in the crystal structure.
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