1-(2-Chloro-1,3-thiazol-5-ylmethyl)-3,5-dimethyl-2-nitrimino-1,2,3,4,5,6-hexahydro-1,3,5-triazine

In the title compound, C9H13ClN6O2S, all bond lengths and angles are normal. The 1,3,5-triazine ring exhibits a half-chair conformation. In the crystal structure, weak intermolecular C—H⋯N and C—H⋯O hydrogen bonds link the molecules into layers parallel to the bc plane.

In the title compound, C 9 H 13 ClN 6 O 2 S, all bond lengths and angles are normal. The 1,3,5-triazine ring exhibits a half-chair conformation. In the crystal structure, weak intermolecular C-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds link the molecules into layers parallel to the bc plane.

Related literature
For synthesis of the title compound, see: Frank et al. (1990). For related crystal structures, see: Zurn et al. (1982). For useful applications of related compounds, see: Motohiro (2000).

Experimental
Crystal data  Table 1 Hydrogen-bond geometry (Å , ). 1-(2-Chloro-1,3-thiazol-5-ylmethyl)-3,5-dimethyl-2-nitrimino-1,2,3,4,5,6-hexahydro-1,3,5-triazine represented by imidacloprid, the only major new class of chemical insecticides of the last three decades. They are increasingly utilized throughout the world (billion-dollar-a-year market), and seven neonicotinoid insecticide are commercialized or nearly on the market at present and expected to become fourth major insecticide group following the organophosphates, methylcarbamates and pyrethroids (Motohiro, 2000). Clothianidin is a neonicotinoid insecticide that was synthesized in Japan by Takeda Chemical. The title compound (I) was synthesized as an intermediate for the synthesis of clothianidin. We report here the crystal structure of (I).
Experimental 1,5-Dimethyl-2-nitroiminohexahydro-1,3,5-triazine1.72 g (0.01 mol) was dissolved in 20 ml of dried DMF. To the solution, 60% sodium hydride 0.28 g(0.012 mol) was added portionwise with cooling. The mixture was stirred for 1 h at room temperature until evolution of hydrogen was ceased and then the mixture was heated with strring further for 1 h at 50° C. To the mixture, a solution of 2-chloro-5-thiazolymethylchloride1.72 g (0.01 mol) in 8 ml of dried DMF was added dropwise at 40-50° C. After this additon,the reaction mixture was heated with strring for two hours at 70-80° C. The mixture was poured into ice-water and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and dichloromethane was distilled off. The residue was purified by a column chromatography to obtain the title compound(0.82 g, yield 27%)· (Frank et al., 1990). Single crystals suitable for X-ray measurement were obtained by recrystallization from dichloromethane at room temperature.

Refinement
All H atoms were placed in idealized positions and constrained to ride on their parent atoms (C-H 0.93-0.97 Å), with U iso (H) values set at 1.5 U eq (C)(for CH3) or 1.2 U eq (C)(for CH2, thiazole CH).