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 R22(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.

Keywords

• crystal structure
• dithiocarbazate
• 5-bromoisatin
• z configuration
• hydrogen bonding
• halogen bond