Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis
The title compound, C10H8ClNO5S, which has potential analgesic activity, crystallizes in space group P21/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.....
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2020-10-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989020012566 |
| _version_ | 1818321574589104128 |
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| author | Svitlana V. Shishkina Lidiya A. Petrushova Kateryna O. Burian Andrii I. Fedosov Igor V. Ukrainets |
| author_facet | Svitlana V. Shishkina Lidiya A. Petrushova Kateryna O. Burian Andrii I. Fedosov Igor V. Ukrainets |
| author_sort | Svitlana V. Shishkina |
| collection | DOAJ |
| description | The title compound, C10H8ClNO5S, which has potential analgesic activity, crystallizes in space group P21/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(SO2) 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%. |
| first_indexed | 2024-12-13T10:43:04Z |
| format | Article |
| id | doaj.art-45391d17d89e4e8b901bc9c428dfca7e |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-13T10:43:04Z |
| publishDate | 2020-10-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-45391d17d89e4e8b901bc9c428dfca7e2022-12-21T23:50:22ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-10-0176101657166010.1107/S2056989020012566pk2647Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysisSvitlana V. Shishkina0Lidiya A. Petrushova1Kateryna O. Burian2Andrii I. Fedosov3Igor V. Ukrainets4SSI Institute for Single Crystals' National Academy of Science of Ukraine, 60 Nauky ave., Kharkiv 61001, UkraineNational University of Pharmacy, 4 Valentynivska St, Kharkiv 61168, UkraineNational University of Pharmacy, 4 Valentynivska St, Kharkiv 61168, UkraineNational University of Pharmacy, 4 Valentynivska St, Kharkiv 61168, UkraineNational University of Pharmacy, 4 Valentynivska St, Kharkiv 61168, UkraineThe title compound, C10H8ClNO5S, which has potential analgesic activity, crystallizes in space group P21/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(SO2) 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%.http://scripts.iucr.org/cgi-bin/paper?S2056989020012566benzothiazine derivativemolecular structurecrystal structurehirshfeld surface analysis |
| spellingShingle | Svitlana V. Shishkina Lidiya A. Petrushova Kateryna O. Burian Andrii I. Fedosov Igor V. Ukrainets Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis Acta Crystallographica Section E: Crystallographic Communications benzothiazine derivative molecular structure crystal structure hirshfeld surface analysis |
| title | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_full | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_fullStr | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_full_unstemmed | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_short | Methyl 5-chloro-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate: structure and Hirshfeld surface analysis |
| title_sort | methyl 5 chloro 4 hydroxy 2 2 dioxo 1h 2λ6 1 benzothiazine 3 carboxylate structure and hirshfeld surface analysis |
| topic | benzothiazine derivative molecular structure crystal structure hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989020012566 |
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