4-[(5-Chloro-2-hy-droxy-benzyl-idene)amino]-3-ethyl-1H-1,2,4-triazole-5(4H)-thione

Abstract

The title compound, C11H11ClN4OS, crystallizes with two mol-ecules, A and B, in the asymmetric unit in which the dihedral angles between the triazole and benzene rings are 54.6 (3) and 56.0 (3)°. Both mol-ecules feature an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring. In the crystal, A-B dimers are linked by pairs of weak C-H⋯S hydrogen bonds along with π-π stacking inter-actions between the triazole rings [centroid-centroid separations = 3.631 (3) and 3.981 (4)Å]. N-H⋯S hydrogen bonds link the dimers into [100] chains, which feature R 2 (2)(8) loops.

Fig. 1.

The view of the structure of (I) with displacement ellipsoids drawn at the 30% probability level. Dotted lines indicate hydrogen bonds and π–π interactions.

Fig. 2.

A part of the crystal structure I showing formation of a chain of R22(8) hydrogen-bonded rings and π–π stacking between Cg1 and Cg2 rings; Cg1: C1/C2/N1/N2/N3, Cg2: C12/C13/N5/N6/N7, Symmetry codes: i) x, y, z+1; ii) x, y, z-1.