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Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate
The title compounds, C(17)H(13)NO(2)S, (I), C(17)H(13)NO(3)S, (II), and C(24)H(17)ClN(2)O(5)S·CHCl(3), (III), are indole derivatives. Compounds (I) and (II) crystalize with two independent molecules in the asymmetric unit. The indole ring systems in all three structures deviate only slightly from p...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2015
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4555396/ https://www.ncbi.nlm.nih.gov/pubmed/26396842 http://dx.doi.org/10.1107/S2056989015014917 |
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author | Gopinath, S. Sethusankar, K. Ramalingam, Bose Muthu Mohanakrishnan, Arasambattu K. |
author_facet | Gopinath, S. Sethusankar, K. Ramalingam, Bose Muthu Mohanakrishnan, Arasambattu K. |
author_sort | Gopinath, S. |
collection | PubMed |
description | The title compounds, C(17)H(13)NO(2)S, (I), C(17)H(13)NO(3)S, (II), and C(24)H(17)ClN(2)O(5)S·CHCl(3), (III), are indole derivatives. Compounds (I) and (II) crystalize with two independent molecules in the asymmetric unit. The indole ring systems in all three structures deviate only slightly from planarity, with dihedral angles between the planes of the pyrrole and benzene rings spanning the tight range 0.20 (9)–1.65 (9)°. These indole ring systems, in turn, are almost orthogonal to the phenylsulfonyl rings [range of dihedral angles between mean planes = 77.21 (8)–89.26 (8)°]. In the three compounds, the molecular structure is stabilized by intramolecular C—H⋯O hydrogen bonds, generating S(6) ring motifs with the sulfone O atom. In compounds (I) and (II), the two independent molecules are linked by C—H⋯O hydrogen bonds and C—H⋯π interactions, while in compound (III), the molecules are linked by C—H⋯O hydrogen bonds, generating R (2) (2)(22) inversion dimers. |
format | Online Article Text |
id | pubmed-4555396 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45553962015-09-22 Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate Gopinath, S. Sethusankar, K. Ramalingam, Bose Muthu Mohanakrishnan, Arasambattu K. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, C(17)H(13)NO(2)S, (I), C(17)H(13)NO(3)S, (II), and C(24)H(17)ClN(2)O(5)S·CHCl(3), (III), are indole derivatives. Compounds (I) and (II) crystalize with two independent molecules in the asymmetric unit. The indole ring systems in all three structures deviate only slightly from planarity, with dihedral angles between the planes of the pyrrole and benzene rings spanning the tight range 0.20 (9)–1.65 (9)°. These indole ring systems, in turn, are almost orthogonal to the phenylsulfonyl rings [range of dihedral angles between mean planes = 77.21 (8)–89.26 (8)°]. In the three compounds, the molecular structure is stabilized by intramolecular C—H⋯O hydrogen bonds, generating S(6) ring motifs with the sulfone O atom. In compounds (I) and (II), the two independent molecules are linked by C—H⋯O hydrogen bonds and C—H⋯π interactions, while in compound (III), the molecules are linked by C—H⋯O hydrogen bonds, generating R (2) (2)(22) inversion dimers. International Union of Crystallography 2015-08-15 /pmc/articles/PMC4555396/ /pubmed/26396842 http://dx.doi.org/10.1107/S2056989015014917 Text en © Gopinath et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Gopinath, S. Sethusankar, K. Ramalingam, Bose Muthu Mohanakrishnan, Arasambattu K. Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate |
title | Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate |
title_full | Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate |
title_fullStr | Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate |
title_full_unstemmed | Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate |
title_short | Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate |
title_sort | crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1h-indole, 4-phenylsulfonyl-3h,4h-cyclopenta[b]indol-1(2h)-one and 1-{2-[(e)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1h-indol-3-yl}ethan-1-one chloroform monosolvate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4555396/ https://www.ncbi.nlm.nih.gov/pubmed/26396842 http://dx.doi.org/10.1107/S2056989015014917 |
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