Synthesis and Crystal Structure of N-(1,3,4-Thiadiazol-2-yl)-1-[1-(6-chloropyridin-3-yl)methy]-5-methyl-1H-[1,2,3]triazol-4-carboxamide

The crystal structure of the title compound (C12H10ClN7OS, M-r = 335.78) has been determined by single-crystal X-ray diffraction. The crystal is of triclinic, space group P (1) over bar with a = 8,4093(11), b = 9.4430(12), c = 11.1454(14) angstrom, alpha = 95.508(2), beta = 111.366(2), gamma = 115.259(2)degrees, V = 711.42(16) angstrom(3), Z = 2, D-c = 1.568 g/cm(3), F(000) = 344, mu(MoK alpha) = 0.428 mm(-1), the final R = 0.0476 and wR = 0.1243 for 2353 observed reflections (I > 2 sigma(I)). The dihedral angles between the pyridine and triazole, thiazole and triazole, and pyridine and thiazole rings are 69.2(1), 9.2(1) and 72.7(1)degrees, respectively. Intramolecular C(8)-H(8B)center dot center dot center dot O(1) and N(5)-H(5A)center dot center dot center dot N(4) as well as intermolecular C(5)-H(5)center dot center dot center dot S(1), C(3)-H(3)center dot center dot center dot N(6) and N(5)-H(5A)center dot center dot center dot N(1) hydrogen bonds together with weak C-H center dot center dot center dot pi hydrogen-bonding and pi-pi stacking interactions contribute to the stability of the structure. There is also evidence for significant electron delocalization in the triazolyl system.