Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamide
In the title compounds, C22H16FNO2S2 (I) and C26H20FNO2S2 (II), the benzothiophene rings are essentially planar with maximum deviations of 0.009 (1) and 0.001 (1) Å for the carbon and sulfur atom in compounds I and II, respectively. In I, the thiophene ring system is almost orthogonal to the phenyl...
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| Format: | Article |
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International Union of Crystallography
2023-08-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989023006096 |
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| author | S. Madhan M. NizamMohideen Vinayagam Pavunkumar Arasambattu K. MohanaKrishnan |
| author_facet | S. Madhan M. NizamMohideen Vinayagam Pavunkumar Arasambattu K. MohanaKrishnan |
| author_sort | S. Madhan |
| collection | DOAJ |
| description | In the title compounds, C22H16FNO2S2 (I) and C26H20FNO2S2 (II), the benzothiophene rings are essentially planar with maximum deviations of 0.009 (1) and 0.001 (1) Å for the carbon and sulfur atom in compounds I and II, respectively. In I, the thiophene ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group, with a dihedral angle of 77.7 (1)°. In compound I, the molecular structure is stabilized by weak C—H...O intramolecular interactions formed by the sulfone oxygen atoms, which generate two S(5) ring motifs. In the crystal of I, N—H...O hydrogen bonds link the molecules into R22(8) rings, which are connected into a C(10) chain via C—H...F hydrogen bonds. Intermolecular C—H...π interactions are also observed. In compound II, the molecules are linked via C—H...O and C—H...F hydrogen bonding, generating infinite C(11) and C(13) chains running parallel to [010]. |
| first_indexed | 2024-03-12T02:26:19Z |
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| id | doaj.art-bf7c907817b44440b582ceecfbf28bd2 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-03-12T02:26:19Z |
| publishDate | 2023-08-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-bf7c907817b44440b582ceecfbf28bd22023-09-05T13:04:53ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-08-0179874174610.1107/S2056989023006096zn2029Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamideS. Madhan0M. NizamMohideen1Vinayagam Pavunkumar2Arasambattu K. MohanaKrishnan3Department of Physics, The New College, Chennai 600 014, University of Madras, Tamil Nadu, IndiaDepartment of Physics, The New College, Chennai 600 014, University of Madras, Tamil Nadu, IndiaDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-600 025, Tamilnadu, IndiaDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-600 025, Tamilnadu, IndiaIn the title compounds, C22H16FNO2S2 (I) and C26H20FNO2S2 (II), the benzothiophene rings are essentially planar with maximum deviations of 0.009 (1) and 0.001 (1) Å for the carbon and sulfur atom in compounds I and II, respectively. In I, the thiophene ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group, with a dihedral angle of 77.7 (1)°. In compound I, the molecular structure is stabilized by weak C—H...O intramolecular interactions formed by the sulfone oxygen atoms, which generate two S(5) ring motifs. In the crystal of I, N—H...O hydrogen bonds link the molecules into R22(8) rings, which are connected into a C(10) chain via C—H...F hydrogen bonds. Intermolecular C—H...π interactions are also observed. In compound II, the molecules are linked via C—H...O and C—H...F hydrogen bonding, generating infinite C(11) and C(13) chains running parallel to [010].http://scripts.iucr.org/cgi-bin/paper?S2056989023006096crystal structurethiophenebenzothiopheneflurophenylphenylsulfonamide hydrogen bondinghirshfeld surface analysis |
| spellingShingle | S. Madhan M. NizamMohideen Vinayagam Pavunkumar Arasambattu K. MohanaKrishnan Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamide Acta Crystallographica Section E: Crystallographic Communications crystal structure thiophene benzothiophene flurophenyl phenylsulfonamide hydrogen bonding hirshfeld surface analysis |
| title | Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamide |
| title_full | Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamide |
| title_fullStr | Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamide |
| title_full_unstemmed | Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamide |
| title_short | Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamide |
| title_sort | crystal structure determination and hirshfeld surface analysis of two new thiophene derivatives e n 2 2 benzo b thiophen 2 yl ethenyl 5 fluorophenyl benzenesulfonamide and e n 2 2 benzo b thiophen 2 yl ethenyl 5 fluorophenyl n but 2 yn 1 yl benzenesulfonamide |
| topic | crystal structure thiophene benzothiophene flurophenyl phenylsulfonamide hydrogen bonding hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989023006096 |
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