Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate

Abstract

The title compound, C10H8BrN3OS2, a brominated dithiocarbazate imine derivative, was obtained from the condensation reaction of S-methyldithiocarbazate (SMDTC) and 5-bromoisatin. The essentially planar molecule exhibits a Z configuration, with the dithiocarbazate and 5-bromoisatin fragments located on the same sides of the C=N azomethine bond, which allows for the formation of an intramolecular N—H...Ob (b = bromoisatin) hydrogen bond generating an S(6) ring motif. In the crystal, adjacent molecules are linked by pairs of N—H...O hydrogen bonds, forming dimers characterized by an R 2 2(8) loop motif. In the extended structure, molecules are linked into a three-dimensional network by C—H...S and C—H...Br hydrogen bonds, C—Br...S halogen bonds and aromatic π–π stacking.