Crystal structure and antimycobacterial evaluation of 2-(cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one
The title compound, C15H15F3N2O3S, crystallizes in the monoclinic system, space group I2/a, with Z = 8. As expected, the nine-membered heterobicyclic system is virtually planar and the cyclohexyl group adopts a chair conformation. There is structural evidence for intramolecular N—S...O chalcogen bon...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-12-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989023010137 |
| _version_ | 1797403904116260864 |
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| author | Adrian Richter Richard Goddard Peter Imming Rüdiger W. Seidel |
| author_facet | Adrian Richter Richard Goddard Peter Imming Rüdiger W. Seidel |
| author_sort | Adrian Richter |
| collection | DOAJ |
| description | The title compound, C15H15F3N2O3S, crystallizes in the monoclinic system, space group I2/a, with Z = 8. As expected, the nine-membered heterobicyclic system is virtually planar and the cyclohexyl group adopts a chair conformation. There is structural evidence for intramolecular N—S...O chalcogen bonding between the benzisothiazolinone S atom and one O atom of the nitro group, approximately aligned along the extension of the covalent N—S bond [N—S...O = 162.7 (1)°]. In the crystal, the molecules form centrosymmetric dimers through C—H...O weak hydrogen bonding between a C—H group of the electron-deficient benzene ring and the benzothiazolinone carbonyl O atom with an R22(10) motif. In contrast to the previously described N-acyl 7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-ones, the title N-cyclohexylmethyl analogue does not inhibit growth of Mycobacterium aurum and Mycobacterium smegmatis in vitro. |
| first_indexed | 2024-03-09T02:45:18Z |
| format | Article |
| id | doaj.art-6158fe0e49f6401e957ae0b343676661 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-03-09T02:45:18Z |
| publishDate | 2023-12-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-6158fe0e49f6401e957ae0b3436766612023-12-05T17:04:07ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-12-0179121194119810.1107/S2056989023010137vm2292Crystal structure and antimycobacterial evaluation of 2-(cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-oneAdrian Richter0Richard Goddard1Peter Imming2Rüdiger W. Seidel3Institut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120 Halle (Saale), GermanyMax-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, GermanyInstitut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120 Halle (Saale), GermanyInstitut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120 Halle (Saale), GermanyThe title compound, C15H15F3N2O3S, crystallizes in the monoclinic system, space group I2/a, with Z = 8. As expected, the nine-membered heterobicyclic system is virtually planar and the cyclohexyl group adopts a chair conformation. There is structural evidence for intramolecular N—S...O chalcogen bonding between the benzisothiazolinone S atom and one O atom of the nitro group, approximately aligned along the extension of the covalent N—S bond [N—S...O = 162.7 (1)°]. In the crystal, the molecules form centrosymmetric dimers through C—H...O weak hydrogen bonding between a C—H group of the electron-deficient benzene ring and the benzothiazolinone carbonyl O atom with an R22(10) motif. In contrast to the previously described N-acyl 7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-ones, the title N-cyclohexylmethyl analogue does not inhibit growth of Mycobacterium aurum and Mycobacterium smegmatis in vitro.http://scripts.iucr.org/cgi-bin/paper?S2056989023010137benzisothiazolinonebenzothiazinonemycobacteriahydrogen bondingcrystal structure |
| spellingShingle | Adrian Richter Richard Goddard Peter Imming Rüdiger W. Seidel Crystal structure and antimycobacterial evaluation of 2-(cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one Acta Crystallographica Section E: Crystallographic Communications benzisothiazolinone benzothiazinone mycobacteria hydrogen bonding crystal structure |
| title | Crystal structure and antimycobacterial evaluation of 2-(cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one |
| title_full | Crystal structure and antimycobacterial evaluation of 2-(cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one |
| title_fullStr | Crystal structure and antimycobacterial evaluation of 2-(cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one |
| title_full_unstemmed | Crystal structure and antimycobacterial evaluation of 2-(cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one |
| title_short | Crystal structure and antimycobacterial evaluation of 2-(cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one |
| title_sort | crystal structure and antimycobacterial evaluation of 2 cyclohexylmethyl 7 nitro 5 trifluoromethyl benzo d isothiazol 3 2h one |
| topic | benzisothiazolinone benzothiazinone mycobacteria hydrogen bonding crystal structure |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989023010137 |
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