Crystal structure of benzyl 3-(3-methylphenyl)dithiocarbazate

Abstract

In the title compound, C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4)° with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)°. The conformation about the N—N bond is gauche [C—N—N—C = −117.48 (15)°]. Overall, the molecule has the shape of the letter L. In the crystal packing, supramolecular chains along the a axis are formed by N—H...S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered {...HNCS}2 and 10-membered {...HNNH...S}2 synthons. The chains are connected into layers by phenyl–tolyl C—H...π interactions; the layers stack along the c axis with no specific interactions between them.

Keywords

• crystal structure
• hydrogen bonding
• C—H...π interactions
• S-substituted dithiocarbazate