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

• Main Authors: Hoong-Kun Fun, Wan-Sin Loh, Nithinchandra, Balakrishna Kalluraya
• Format: Article
• Language: English
• Published: International Union of Crystallography 2011-05-01
• Series: Acta Crystallographica Section E
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S1600536811013900

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) Å] and forms dihedral angles of 34.76 (4) and 48.67 (4)° with the benzene rings. An intramolecular C—H...O hydrogen bond stabilizes the molecular structure and forms an S(6) ring motif. In the crystal packing, intermolecular N—H...N hydrogen bonds link centrosymmetrically related molecules into dimers, generating R22(8) ring motifs. The dimers are then linked into a three-dimensional network by intermolecular C—H...O and C—H...Cl hydrogen bonds, and by C—H...π interactions. Further stabilization is provided by π–π interactions involving the sydnone rings, with centroid–centroid separations of 3.4198 (5) Å.