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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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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
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author Shyshkina, Mariia O.
Lega, Dmitry A.
Goryachiy, Volodymyr D.
Shemchuk, Ludmila M.
Levashov, Dmitriy V.
Shemchuk, Leonid A.
author_facet Shyshkina, Mariia O.
Lega, Dmitry A.
Goryachiy, Volodymyr D.
Shemchuk, Ludmila M.
Levashov, Dmitriy V.
Shemchuk, Leonid A.
author_sort Shyshkina, Mariia O.
collection PubMed
description 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.
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spelling pubmed-80610962021-05-04 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 Shyshkina, Mariia O. Lega, Dmitry A. Goryachiy, Volodymyr D. Shemchuk, Ludmila M. Levashov, Dmitriy V. Shemchuk, Leonid A. Acta Crystallogr E Crystallogr Commun Research Communications 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. International Union of Crystallography 2021-02-26 /pmc/articles/PMC8061096/ /pubmed/33953954 http://dx.doi.org/10.1107/S2056989021002085 Text en © Shyshkina et al. 2021 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Shyshkina, Mariia O.
Lega, Dmitry A.
Goryachiy, Volodymyr D.
Shemchuk, Ludmila M.
Levashov, Dmitriy V.
Shemchuk, Leonid A.
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8061096/
https://www.ncbi.nlm.nih.gov/pubmed/33953954
http://dx.doi.org/10.1107/S2056989021002085
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