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Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ(6),1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis
The title compound, C(10)H(8)ClNO(5)S, which has potential analgesic activity, crystallizes in space group P2(1)/n. The benzothiazine ring system adopts an intermediate form between sofa and twist-boat conformations. The coplanarity of the ester substituent to the bicyclic fragment is stabilized...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
International Union of Crystallography
2020
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7534242/ https://www.ncbi.nlm.nih.gov/pubmed/33117584 http://dx.doi.org/10.1107/S2056989020012566 |
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| author | Shishkina, Svitlana V. Petrushova, Lidiya A. Burian, Kateryna O. Fedosov, Andrii I. Ukrainets, Igor V. |
| author_facet | Shishkina, Svitlana V. Petrushova, Lidiya A. Burian, Kateryna O. Fedosov, Andrii I. Ukrainets, Igor V. |
| author_sort | Shishkina, Svitlana V. |
| collection | PubMed |
| description | The title compound, C(10)H(8)ClNO(5)S, which has potential analgesic activity, crystallizes in space group P2(1)/n. The benzothiazine ring system adopts an intermediate form between sofa and twist-boat conformations. The coplanarity of the ester substituent to the bicyclic fragment is stabilized by an O—H⋯O intramolecular hydrogen bond. In the crystal, hydrogen bonds of type N—H⋯O(SO(2)) link the molecules into zigzag chains extending along the b-axis direction. Neighbouring chains are linked by both O—H⋯Cl and C—H⋯Cl interactions. A Hirshfeld surface analysis was used to compare different types of intermolecular interactions, giving contributions of O⋯H/H⋯O = 42.0%, C⋯H/H⋯C = 17.3%, Cl⋯H/H⋯Cl = 14.2%, H⋯H = 11.1%. |
| format | Online Article Text |
| id | pubmed-7534242 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2020 |
| publisher | International Union of Crystallography |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-75342422020-10-27 Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ(6),1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis Shishkina, Svitlana V. Petrushova, Lidiya A. Burian, Kateryna O. Fedosov, Andrii I. Ukrainets, Igor V. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(10)H(8)ClNO(5)S, which has potential analgesic activity, crystallizes in space group P2(1)/n. The benzothiazine ring system adopts an intermediate form between sofa and twist-boat conformations. The coplanarity of the ester substituent to the bicyclic fragment is stabilized by an O—H⋯O intramolecular hydrogen bond. In the crystal, hydrogen bonds of type N—H⋯O(SO(2)) link the molecules into zigzag chains extending along the b-axis direction. Neighbouring chains are linked by both O—H⋯Cl and C—H⋯Cl interactions. A Hirshfeld surface analysis was used to compare different types of intermolecular interactions, giving contributions of O⋯H/H⋯O = 42.0%, C⋯H/H⋯C = 17.3%, Cl⋯H/H⋯Cl = 14.2%, H⋯H = 11.1%. International Union of Crystallography 2020-09-18 /pmc/articles/PMC7534242/ /pubmed/33117584 http://dx.doi.org/10.1107/S2056989020012566 Text en © Shishkina et al. 2020 http://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.http://creativecommons.org/licenses/by/4.0/ |
| spellingShingle | Research Communications Shishkina, Svitlana V. Petrushova, Lidiya A. Burian, Kateryna O. Fedosov, Andrii I. Ukrainets, Igor V. Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ(6),1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ(6),1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_full | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ(6),1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_fullStr | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ(6),1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_full_unstemmed | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ(6),1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_short | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ(6),1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_sort | methyl 5-chloro-4-hydroxy-2,2-dioxo-1h-2λ(6),1-benzothiazine-3-carboxylate: structure and hirshfeld surface analysis |
| topic | Research Communications |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7534242/ https://www.ncbi.nlm.nih.gov/pubmed/33117584 http://dx.doi.org/10.1107/S2056989020012566 |
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