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

The title compound, C19H15ClN6O3S, exists in trans and cis configurations with respect to the acyclic C=N bonds. The 3,6-dihydro-2H-1,3,4-thiadiazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.013 (1) angstrom] and forms dihedral angles of 34.76 (4) and 48.67 (4)degrees with the benzene rings. An intramolecular C-H center dot center dot center dot O hydrogen bond stabilizes the molecular structure and forms an S(6) ring motif. In the crystal packing, intermolecular N-H center dot center dot center dot N hydrogen bonds link centrosymmetrically related molecules into dimers, generating R-2(2) (8) ring motifs. The dimers are then linked into a three-dimensional network by intermolecular C-H center dot center dot center dot O and C-H center dot center dot center dot Cl hydrogen bonds, and by C-H center dot center dot center dot pi interactions. Further stabilization is provided by pi-pi interactions involving the sydnone rings, with centroid-centroid separations of 3.4198 (5) angstrom.