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

The title compound, C(22)H(18)N(4)OS, 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).