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Crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (3)
The three title compounds, C(26)H(19)NO(3)S, (1), C(27)H(20)N(2)O(8)S, (2), and C(30)H(19)NO(3)S, (3), are carbazole derivatives, where (1) and (3) are heterocycle-containing carbazoles with a benzofuran moiety fused to a carbazole unit. In (2), a dimethoxynitrophenyl ring is attached to the ca...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5137599/ https://www.ncbi.nlm.nih.gov/pubmed/27980821 http://dx.doi.org/10.1107/S2056989016016819 |
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author | Gangadharan, Rajeswari Narayanan, P. Sethusankar, K. Saravanan, Velu Mohanakrishnan, Arasambattu K. |
author_facet | Gangadharan, Rajeswari Narayanan, P. Sethusankar, K. Saravanan, Velu Mohanakrishnan, Arasambattu K. |
author_sort | Gangadharan, Rajeswari |
collection | PubMed |
description | The three title compounds, C(26)H(19)NO(3)S, (1), C(27)H(20)N(2)O(8)S, (2), and C(30)H(19)NO(3)S, (3), are carbazole derivatives, where (1) and (3) are heterocycle-containing carbazoles with a benzofuran moiety fused to a carbazole unit. In (2), a dimethoxynitrophenyl ring is attached to the carbazole moiety. In the three derivatives, a phenylsulfonyl group is attached to the N atom of the carbazole unit. Compound (1) crystallizes with two independent molecules in the asymmetric unit (A and B). The carbazole skeleton in the three compounds is essentially planar. In compound (1), the benzene ring of the phenylsulfonyl moiety is almost orthogonal to the carbazole moiety, with dihedral angles of 85.42 (9) and 84.52 (9)° in molecules A and B, respectively. The benzene ring of the phenylsulfonyl group in compounds (2) and (3) are inclined to the carbazole moiety, making dihedral angles of 70.73 (13) and 81.73 (12)°, respectively. The S atom has a distorted tetrahedral configuration in all three compounds. In the crystals, C—H⋯O hydrogen bonds give rise to R (2) (2)(12) inversion dimers for compound (1), and to R (2) (2)(24) inversion dimers and R (4) (4)(40) ring motifs for compound (2). The crystal packing in (1) also features C—H⋯π and π–π interactions [shortest intercentroid distance = 3.684 (1) Å], leading to supramolecular three-dimensional aggregation. In the crystal of compound (2), the combination of the various C—H⋯O hydrogen bonds leads to the formation of a three-dimensional network. In the crystal of compound (3), molecules are linked by C—H⋯O hydrogen bonds, forming chains running parallel to the a axis, and the chains are linked by C—H⋯π interactions, forming corrugated sheets parallel to the ab plane. |
format | Online Article Text |
id | pubmed-5137599 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-51375992016-12-15 Crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (3) Gangadharan, Rajeswari Narayanan, P. Sethusankar, K. Saravanan, Velu Mohanakrishnan, Arasambattu K. Acta Crystallogr E Crystallogr Commun Research Communications The three title compounds, C(26)H(19)NO(3)S, (1), C(27)H(20)N(2)O(8)S, (2), and C(30)H(19)NO(3)S, (3), are carbazole derivatives, where (1) and (3) are heterocycle-containing carbazoles with a benzofuran moiety fused to a carbazole unit. In (2), a dimethoxynitrophenyl ring is attached to the carbazole moiety. In the three derivatives, a phenylsulfonyl group is attached to the N atom of the carbazole unit. Compound (1) crystallizes with two independent molecules in the asymmetric unit (A and B). The carbazole skeleton in the three compounds is essentially planar. In compound (1), the benzene ring of the phenylsulfonyl moiety is almost orthogonal to the carbazole moiety, with dihedral angles of 85.42 (9) and 84.52 (9)° in molecules A and B, respectively. The benzene ring of the phenylsulfonyl group in compounds (2) and (3) are inclined to the carbazole moiety, making dihedral angles of 70.73 (13) and 81.73 (12)°, respectively. The S atom has a distorted tetrahedral configuration in all three compounds. In the crystals, C—H⋯O hydrogen bonds give rise to R (2) (2)(12) inversion dimers for compound (1), and to R (2) (2)(24) inversion dimers and R (4) (4)(40) ring motifs for compound (2). The crystal packing in (1) also features C—H⋯π and π–π interactions [shortest intercentroid distance = 3.684 (1) Å], leading to supramolecular three-dimensional aggregation. In the crystal of compound (2), the combination of the various C—H⋯O hydrogen bonds leads to the formation of a three-dimensional network. In the crystal of compound (3), molecules are linked by C—H⋯O hydrogen bonds, forming chains running parallel to the a axis, and the chains are linked by C—H⋯π interactions, forming corrugated sheets parallel to the ab plane. International Union of Crystallography 2016-11-04 /pmc/articles/PMC5137599/ /pubmed/27980821 http://dx.doi.org/10.1107/S2056989016016819 Text en © Gangadharan et al. 2016 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Gangadharan, Rajeswari Narayanan, P. Sethusankar, K. Saravanan, Velu Mohanakrishnan, Arasambattu K. Crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (3) |
title | Crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (3) |
title_full | Crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (3) |
title_fullStr | Crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (3) |
title_full_unstemmed | Crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (3) |
title_short | Crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole, (3) |
title_sort | crystal structures of three carbazole derivatives: 12-ethyl-7-phenylsulfonyl-7h-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimethoxy-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9h-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenylsulfonyl-7h-benzofuro[2,3-b]carbazole, (3) |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5137599/ https://www.ncbi.nlm.nih.gov/pubmed/27980821 http://dx.doi.org/10.1107/S2056989016016819 |
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