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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2021
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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. |
format | Online Article Text |
id | pubmed-8061096 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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