Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole
The title compounds were synthesized by alkylation of 5-[(4-dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiol with benzyl chloride or 2-chloro-6-fluorobenzyl chloride in the presence of potassium carbonate. The yields of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C17H17N3OS (I), a...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-06-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989023004164 |
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| author | Rasul Ya. Okmanov Abdukhakim A. Ziyaev Azimboy Sh. Abdukarimov Turdibek T. Toshmurodov Tursunali S. Kholikov |
| author_facet | Rasul Ya. Okmanov Abdukhakim A. Ziyaev Azimboy Sh. Abdukarimov Turdibek T. Toshmurodov Tursunali S. Kholikov |
| author_sort | Rasul Ya. Okmanov |
| collection | DOAJ |
| description | The title compounds were synthesized by alkylation of 5-[(4-dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiol with benzyl chloride or 2-chloro-6-fluorobenzyl chloride in the presence of potassium carbonate. The yields of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C17H17N3OS (I), and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C17H15ClFN3OS (II), were 96 and 92%, respectively. In the crystal structures of (I) and (II), C–H...π interactions are observed between neighboring molecules. Hirshfeld surface analysis indicates that H...H and H...C/C...H interactions make the most important contributions to the crystal packing. |
| first_indexed | 2024-03-12T02:25:54Z |
| format | Article |
| id | doaj.art-4cae3d8081734256b97a7982462336ae |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-03-12T02:25:54Z |
| publishDate | 2023-06-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-4cae3d8081734256b97a7982462336ae2023-09-05T13:04:47ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-06-0179655255610.1107/S2056989023004164dx2051Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazoleRasul Ya. Okmanov0Abdukhakim A. Ziyaev1Azimboy Sh. Abdukarimov2Turdibek T. Toshmurodov3Tursunali S. Kholikov4S. 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, University Str. 4, Tashkent, 100174, 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, University Str. 4, Tashkent, 100174, UzbekistanThe title compounds were synthesized by alkylation of 5-[(4-dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiol with benzyl chloride or 2-chloro-6-fluorobenzyl chloride in the presence of potassium carbonate. The yields of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C17H17N3OS (I), and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C17H15ClFN3OS (II), were 96 and 92%, respectively. In the crystal structures of (I) and (II), C–H...π interactions are observed between neighboring molecules. Hirshfeld surface analysis indicates that H...H and H...C/C...H interactions make the most important contributions to the crystal packing.http://scripts.iucr.org/cgi-bin/paper?S2056989023004164synthesis1,3,4-oxadiazolecrystal structurehirshfeld surface analysis |
| spellingShingle | Rasul Ya. Okmanov Abdukhakim A. Ziyaev Azimboy Sh. Abdukarimov Turdibek T. Toshmurodov Tursunali S. Kholikov Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole Acta Crystallographica Section E: Crystallographic Communications synthesis 1,3,4-oxadiazole crystal structure hirshfeld surface analysis |
| title | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_full | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_fullStr | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_full_unstemmed | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_short | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_sort | syntheses crystal structures and hirshfeld surface analysis of 2 benzylsulfanyl 5 4 dimethylamino phenyl 1 3 4 oxadiazole and 2 2 chloro 6 fluorobenzyl sulfanyl 5 4 dimethylamino phenyl 1 3 4 oxadiazole |
| topic | synthesis 1,3,4-oxadiazole crystal structure hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989023004164 |
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