S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]-dithiocarbazate: Crystal structure and Hirshfeld surface analysis

Abstract

In the title dithiocarbazate ester, C16H17N3S2 (systematic name: (Z)-{[(benzylsulfanyl) methanethioyl]amino}[1-(6-methylpyridin-2-yl)ethylidene]amine), the central methylidenehydrazinecarbodithioate (C2N2S2) core is almost planar (r.m.s. deviation = 0.0111 A ) and forms dihedral angles of 71.67 (3) with the approximately orthogonally inclined thioester phenyl ring, and 7.16 (7) with the approximately coplanar substituted pyridyl ring. The latter arrangement and the Z configuration about the imine-C N bond allows for the formation of an intramolecular hydrazine-N-HN(pyridyl) hydrogen bond that closes an S(6) loop. In the crystal, phenyl-C-HS(thione), methylene-C-H(pyridyl), methylene- and phenyl-C-H(phenyl) contacts connect molecules into supramolecular layers propagating in the bc plane; the layers stack along the a axis with no directional interactions between them. The analysis of the Hirshfeld surface indicates the relative importance of an intralayer phenyl-HH(pyridyl) contact upon the molecular packing.