2-Amino-4-(4-chloro-1-ethyl-2,2-dioxo-1H-benzo[c][1,2]thiazin-3-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile: single-crystal X-ray diffraction study and Hirshfeld surface analysis

Abstract

In the title compound, C22H22ClN3O4S, which has potential non-steroidal anti-inflammatory activity, the benzothiazine and cyclohexenone rings both adopt a distorted sofa conformation while the 4H-pyrane ring adopts a very flattened sofa conformation. The two bicyclic fragments are skewed to each other, with the dihedral angle between their least-squares planes being 72.8 (1)°. In the crystal, the molecules form a hydrogen-bonded chain parallel to the a axis due to N—H...O and N—H...Cl hydrogen bonds. Neighbouring chains are linked by C—H...N, C—H...O and π–π stacking interactions. Hirshfeld surface analysis was used to investigate the importance of the different types of intermolecular interactions whose contributions are: H...H = 44.7%, O...H/H...O = 21.8%, N...H/H...N = 11.9%, C...H/H...C = 9.5%, Cl...H/H...Cl = 7.2%. Parts of the molecule, viz. the phenyl ring and the ethyl side chain, are equally disordered over two sets of sites.

Keywords

• 1h-benzo[c][1,2]thiazine
• 2,2-dioxide
• 4h-pyran
• multicomponent reaction
• molecular structure
• crystal structure
• hirshfeld surface analysis