Synthesis and Crystal Structure of 5-(p-Tolyl)-4-[2-(2,4-dichlorophenoxy)acetamido]-1,2,4-triazole-3-thione Ethyl Acetate Solvate

A novel compound 5-(p-tolyl)-4-[2-(2,4-dichlorophenoxy)acetamido]-1,2,4-tria zole- 3-thione 2a has been synthesized by the reaction of 5-(p-tolyl)-4-amino-1,2,4-triazole-3-thione 1 with 2-(2,4-dichlorophenoxy)acetyl chloride. Interestingly, the title compound 2 was obtained when 2a crystallizes from a mixed solution of petroleum ether and ethyl acetate, and it has been characterized by elemental analysis, IR, 1H NMR spectra and single-crystal X-ray diffraction. The crystal belongs to the triclinic system, space group P1 with a = 9.780(5), b = 10.876(6), c = 11.615(6), α = 104.822(7), β = 94.105(6), γ = 94.305(6)°, V = 1185.7(11)3, Z = 2, μ = 0.397 mm–1, Mr = 497.39, Dx = 1.393 g/cm3, F(000) = 516, S = 1.097, the final R = 0.0730 and wR = 0.2133 for 4111 unique reflections (Rint = 0.0525) with 3212 observed ones. The dihedral angles made by the triazole ring with the methyl- and chloro-substituted benzene rings are 43.5(7) and 50.2(9)°, respectively. Some intra- and intermolecular hydrogen bonds together with C–H···π interactions existing in the lattice stabilize the crystal structure.