Syntheses, crystal structures and Hirshfeld surface analyses of N-arylsulfonyl derivatives of cytisine
By arylsulfonylation of cytisine in the presence of triethylamine, three new compounds have been obtained in good yields: (7R,9R)-N-[(4-ethylphenyl)sulfonyl]cytisine, C19H22N2O3S (I) {systematic name: (1R,5R)-3-[(4-ethylphenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-...
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| Natura: | Articolo |
| Lingua: | English |
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International Union of Crystallography
2023-04-01
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| Serie: | Acta Crystallographica Section E: Crystallographic Communications |
| Soggetti: | |
| Accesso online: | http://scripts.iucr.org/cgi-bin/paper?S2056989023001950 |
| _version_ | 1827971760967909376 |
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| author | Rasul Ya. Okmanov Manzura I. Olimova Surayyo B. Karabaeva Frunza A. Sapaev Kudaybergen B. Abdireymov |
| author_facet | Rasul Ya. Okmanov Manzura I. Olimova Surayyo B. Karabaeva Frunza A. Sapaev Kudaybergen B. Abdireymov |
| author_sort | Rasul Ya. Okmanov |
| collection | DOAJ |
| description | By arylsulfonylation of cytisine in the presence of triethylamine, three new compounds have been obtained in good yields: (7R,9R)-N-[(4-ethylphenyl)sulfonyl]cytisine, C19H22N2O3S (I) {systematic name: (1R,5R)-3-[(4-ethylphenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one}, (7R,9R)-N-[(4-chlorophenyl)sulfonyl]cytisine, C17H17ClN2O3S (II) {systematic name: (1R,5R)-3-[(4-chlorophenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one} and (7R,9R)-N-[(3-nitrophenyl)sulfonyl]cytisine, C17H17N3O5S (III) {systematic name: (1R,5R)-3-[(3-nitrophenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one}. The crystal structures of the compounds were determined on the basis of single-crystal X-ray diffraction data. The crystal structures of (I)–(III) are distinguished by the arrangement of two fragments of the molecule around the sulfonyl site. For all structures, weak C—H...O hydrogen bonds are developed. Hirshfeld surface analysis shows that H...H (for I and II) and H...O/O...H (for III) interactions make the most important contribution to the crystal packing. |
| first_indexed | 2024-04-09T19:13:08Z |
| format | Article |
| id | doaj.art-062603dc2c2d40cf83a7dfbac363356f |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-09T19:13:08Z |
| publishDate | 2023-04-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-062603dc2c2d40cf83a7dfbac363356f2023-04-06T09:42:30ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-04-0179431331810.1107/S2056989023001950wm5674Syntheses, crystal structures and Hirshfeld surface analyses of N-arylsulfonyl derivatives of cytisineRasul Ya. Okmanov0Manzura I. Olimova1Surayyo B. Karabaeva2Frunza A. Sapaev3Kudaybergen B. Abdireymov4S. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent, 100170, UzbekistanS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent, 100170, UzbekistanNational University of Uzbekistan named after Mirzo Ulugbek, massif Universitet shakharchasi 4, Tashkent, 100174, UzbekistanNational University of Uzbekistan named after Mirzo Ulugbek, massif Universitet shakharchasi 4, Tashkent, 100174, UzbekistanKara-Kalpak State University, acad. Abdirov Str., 1, Nukus, 742000, UzbekistanBy arylsulfonylation of cytisine in the presence of triethylamine, three new compounds have been obtained in good yields: (7R,9R)-N-[(4-ethylphenyl)sulfonyl]cytisine, C19H22N2O3S (I) {systematic name: (1R,5R)-3-[(4-ethylphenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one}, (7R,9R)-N-[(4-chlorophenyl)sulfonyl]cytisine, C17H17ClN2O3S (II) {systematic name: (1R,5R)-3-[(4-chlorophenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one} and (7R,9R)-N-[(3-nitrophenyl)sulfonyl]cytisine, C17H17N3O5S (III) {systematic name: (1R,5R)-3-[(3-nitrophenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one}. The crystal structures of the compounds were determined on the basis of single-crystal X-ray diffraction data. The crystal structures of (I)–(III) are distinguished by the arrangement of two fragments of the molecule around the sulfonyl site. For all structures, weak C—H...O hydrogen bonds are developed. Hirshfeld surface analysis shows that H...H (for I and II) and H...O/O...H (for III) interactions make the most important contribution to the crystal packing.http://scripts.iucr.org/cgi-bin/paper?S2056989023001950alkaloidcytisinearylsulfonylationsynthesiscrystal structurehirshfeld surface analysis |
| spellingShingle | Rasul Ya. Okmanov Manzura I. Olimova Surayyo B. Karabaeva Frunza A. Sapaev Kudaybergen B. Abdireymov Syntheses, crystal structures and Hirshfeld surface analyses of N-arylsulfonyl derivatives of cytisine Acta Crystallographica Section E: Crystallographic Communications alkaloid cytisine arylsulfonylation synthesis crystal structure hirshfeld surface analysis |
| title | Syntheses, crystal structures and Hirshfeld surface analyses of N-arylsulfonyl derivatives of cytisine |
| title_full | Syntheses, crystal structures and Hirshfeld surface analyses of N-arylsulfonyl derivatives of cytisine |
| title_fullStr | Syntheses, crystal structures and Hirshfeld surface analyses of N-arylsulfonyl derivatives of cytisine |
| title_full_unstemmed | Syntheses, crystal structures and Hirshfeld surface analyses of N-arylsulfonyl derivatives of cytisine |
| title_short | Syntheses, crystal structures and Hirshfeld surface analyses of N-arylsulfonyl derivatives of cytisine |
| title_sort | syntheses crystal structures and hirshfeld surface analyses of n arylsulfonyl derivatives of cytisine |
| topic | alkaloid cytisine arylsulfonylation synthesis crystal structure hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989023001950 |
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