4-{2-[2-(4-Chlorobenzylidene)hydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenylsydnone

Abstract

The title compound, C18H13ClN6O2S, exists in trans and cis configurations with respect to the acyclic C=N bonds [C=N = 1.2837 (15) and 1.3000 (14) Å, respectively]. The 3,6-dihydro-2H-1,3,4-thiadiazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.002 (1) Å] and forms dihedral angles of 50.45 (7) and 61.21 (6)° with the aromatic rings. In the crystal, intermolecular N—H...N, C—H...Cl and C—H...S hydrogen bonds link the molecules into layers parallel to ab plane. The crystal packing is stabilized by C—H...π interactions and further consolidated by π–π interactions involving the phenyl rings [centroid–centroid distance = 3.6306 (7) Å].