Crystal structure of (Z)-2-(1-benzyl-2-oxoindolin-3-ylidene)-N-phenylhydra-zine-1-carbothioamide

Abstract

The title compound, C22H18N4OS, crystallized with four independent molecules (A, B, C and D) in the asymmetric unit. All four molecules have a Z conformation about the C=N bond with the benzyl ring being inclined to the indoline ring mean planes by 73.4 (2), 77.9 (2), 73.2 (2) and 77.2 (2)° in molecules A, B, C and D, respectively. In molecules A and B, the phenyl ring is inclined to the mean plane of the indoline ring mean plane by 12.0 (2) and 12.2 (2)°, respectively. However, in molecules C and D, the same dihedral angles are larger, viz. 37.3 (2) and 36.4 (2)°, respectively. Consequently, the benzyl and phenyl rings are almost normal to one another in molecules A and B [dihedral angles = 80.3 (3) and 87.1 (3)°, respectively], while in molecules C and D, the same dihedral angles are only 48.8 (2) and 43.8 (3)°, respectively. There is an intramolecular N - H⋯O hydrogen bond in each molecule with an S(6) ring motif. There are also short intramolecular N - H⋯N and C - H⋯S contacts in each molecule. In the crystal, molecules are linked via C - H⋯S hydrogen bonds and C - H⋯π interactions, forming a three-dimensional structure. The crystal was refined as a non-merohedral twin with a final BASF value of 0.110 (1).