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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

In the title compound, C(22)H(22)ClN(3)O(4)S, 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...

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Detalles Bibliográficos
Autores principales: Shyshkina, Mariia O., Lega, Dmitry A., Goryachiy, Volodymyr D., Shemchuk, Ludmila M., Levashov, Dmitriy V., Shemchuk, Leonid A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8061096/
https://www.ncbi.nlm.nih.gov/pubmed/33953954
http://dx.doi.org/10.1107/S2056989021002085
Descripción
Sumario:In the title compound, C(22)H(22)ClN(3)O(4)S, 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.