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 antiinflammatory 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—HO and N—HCl hydrogen bonds. Neighbouring chains are linked by C—HN, C—HO and – stacking interactions. Hirshfeld surface analysis was used to investigate the importance of the different types of intermolecular interactions whose contributions are: HH = 44.7%, OH/HO = 21.8%, NH/HN = 11.9%, CH/HC = 9.5%, ClH/HCl = 7.2%. Parts of the molecule, viz. the phenyl ring and the ethyl side chain, are equally disordered over two sets of sites.