(E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide

The title compound, C17H15N3OS, crystallizes with two unique molecules, denoted 1 and 2, in the asymmetric unit. The two molecules are closely similar and overlay with an r.m.s. deviation of 0.053 angstrom. Both molecules adopt E configurations with respect to the C=N bonds. The dihedral angles between the benzothiophene groups and N-bound phenyl rings are 36.36 (9)degrees for molecule 1 and 29.71 (9)degrees for molecule 2. The C=N-NH-C(O)NH ethylidene-hydrazinecarboxamide units are also reasonably planar, with r.m.s. deviations of 0.061 and 0.056 angstrom, respectively, for the two molecules. The methyl substituents lie 0.338 (3) and 0.396 (3) angstrom, respectively, from these planes. The C=N-NH-C(O)NH planes are inclined to the phenyl rings at 13.65 (11) and 15.56 (11)degrees, respectively, in molecules 1 and 2. This conformation is enhanced by weak intramolecular C-H center dot center dot center dot O hydrogen bonds between ortho-H atoms of the two phenyl rings and the carbonyl O atoms, which generate S(6) rings in each molecule. In the crystal, pairs of molecules are linked by pairs of intermolecular N-H center dot center dot center dot O hydrogen bonds into dimers. Alternating dimers are further interconnected by weak C-H center dot center dot center dot O contacts into zigzag rows along b. The rows are stacked along a by C-H center dot center dot center dot pi contacts involving the benzene ring from molecule 2 and the thiophene ring from molecule 1 of adjacent benzothiophene units.