Source of materialThe title compound was prepared by the reaction of 4-amino-5-(2-ethoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione (0.002 mol) and 1-chloro-2,4-dinitrobenzene (0.002 mol) in the mixed solution of triethylamine (10 ml) and ethanol (20 ml). The triazole was synthesized following the literature method of [1]. The desired product was obtained by filtration, drying and recrystallization from ethanol. Single crystals suitable for ray data collection were obtained by slow evaporation of amethanol solution.
Experimental detailsThe H1D and H1E atoms were refined subject to the restraint d(N-H) =0.85(2) Å.The other Hatoms were positioned geometrically and allowed to ride on their parent atoms at distances.96 or 0.97 Å with U iso =1.5 U eq (parent atom). The huge Rvalues may be attributed to the too thin in one direction of the sample crystal.
DiscussionRecently, the compounds containing 1,2,4-triazole group have attracted much interest because of their exhibiting various biological activities [2-6], such as anti-inflammatory, analgesic, and anti-fungal activities. They can be used as plant growth-inhibitors [7], dyes for improved preservability and absorption characteristics [8], paints and surface active agents [9] and inhibitors of malignant cellular proliferation [10]. But thioethers of 1,2,4-triazole derivatives possess more biological activities than their matrix 1,2,4-triazoles [11,12]. In the title crystal structure, the five-membered triazole ring and the benzene ring are essentially planar, even the maximum deviation from the mean plane of the benzene ring (C3-C8) is only 0.018°. The benzene ring (C3-C8) and the triazole ring form adihedral angle of 47.2(2)°, while the dihedral angle betweent he benzene ring (C11-C16) and the triazole ring is 69.45°. And the two benzene rings make adihedral angle of 58.7(1)°. The C-N bond lengths in the five-membered triazole ring (1.305(4) -1.316(4) Å)a re longer than at ypical C=N double bond (mean 1.269 Å), but shorter than aC-N single bond (mean 1.443(4) Å) [13][14][15], indicating electron delocalization in the triazole ring.
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