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, Mr = 335.78) has been determined by single-crystal X-ray diffraction. The crystal is of triclinic, space group P(1) with a = 8.4093(11), b = 9.4430(12), c = 11.1454(14) (A), α = 95.508(2), β = 111.366(2), γ = 115.259(2)°, V = 711.42(16) (A)3, Z = 2, Dc = 1.568 g/cm3, F(000) = 344, μ(MoKα) = 0.428 mm-1, the final R = 0.0476 and wR = 0.1243 for 2353 observed reflections (I > 2σ(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)°, respectively. Intramolecular C(8)-H(8B)…O(1) and N(5)-H(5A)…(N(4) as well as intermolecular C(5)-H(5)…(S(1), C(3)-H(3)…(N(6) and N(5)-H(5A)…(N(1) hydrogen bonds together with weak C-H…π hydrogen-bonding and π-π stacking interactions contribute to the stability of the structure. There is also evidence for significant electron delocalization in the triazolyl system.