(E)-4-(4-Hydr-oxy-3-methoxy-benzyl-idene-amino)-3-[1-(4-isobutyl-phen-yl)eth-yl]-1H-1,2,4-triazole-5(4H)-thione

Abstract

The asymmetric unit of the title compound, C(22)H(26)N(4)O(2)S, contains two crystallographically independent mol-ecules (A and B). The isobutyl unit of mol-ecule B is disordered over two orientations with refined occupancies of 0.785 (6) and 0.215 (6). In each mol-ecule, intra-molecular C-H⋯S hydrogen bonds generate S(6) ring motifs. The essentially planar 1,2,4-triazole rings [r.m.s. deviations of 0.004 (2) and 0.011 (2) Å, in A and B respectively] form dihedral angles of 85.86 (12), 8.38 (10)°, respectively, with the isobutyl-substituted phenyl ring and the 2-methoxy-phenol substituent in mol-ecule A [89.26 (13) and 2.46 (10)°, respectively, in B]. In the crystal structure, inter-molecular N-H⋯N and N-H⋯S hydrogen bonds link neighbouring mol-ecules, generating R(2) (2)(7) ring motifs. These molecules are further inter-connected into extended chains along [20] by inter-molecular O-H⋯O hydrogen bonds. The crystal structure is further stabilized by π-π [centroid-centroid distance = 3.6299 (13) Å] and C-H⋯π inter-actions. A short O⋯O contact of 2.781 (2) Å is also observed.

Fig. 1.

The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. Intramolecular hydrogen bonds are shown as dashed lines. Open bonds indicate the minor disorder component.

Fig. 2.

The crystal structure of the title compound, showing R22(7) ring motifs being linked into one-dimensional extended chains. Only the major disorder component is shown. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.