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Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole
In the title indole derivatives, C(22)H(16)N(2)O(5)S, (I) and C(20)H(15)NO(3)S(2), (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16)°, respectively. In both compounds, the sulfonyl S atom has a distorted tet...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5730317/ https://www.ncbi.nlm.nih.gov/pubmed/29250380 http://dx.doi.org/10.1107/S2056989017012804 |
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author | Dhanalakshmi, G. Saravanan, Velu Mohanakrishnan, Arasambattu K. Aravindhan, S. |
author_facet | Dhanalakshmi, G. Saravanan, Velu Mohanakrishnan, Arasambattu K. Aravindhan, S. |
author_sort | Dhanalakshmi, G. |
collection | PubMed |
description | In the title indole derivatives, C(22)H(16)N(2)O(5)S, (I) and C(20)H(15)NO(3)S(2), (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16)°, respectively. In both compounds, the sulfonyl S atom has a distorted tetrahedral geometry [O—S—O = 119.98 (9) and N—S—C = 104.01 (8)° for compound (I) and O—S—O = 120.08 (18) and N—S—C = 104.91 (14)° for compound (II)] and the sum of the bond angles at N indicates sp (2) hybridization. The molecules of both (I) and (II) feature intramolecular C—H⋯O hydrogen bonds that generate S(6) ring motifs with the sulfone O atom. In the crystals, molecules of (I) are linked by C—H—O hydrogen bonds, forming R (4) (4)(18) ring motifs while molecules of (II) are linked by C—H—O and C—H—S hydrogen bonds, forming R (2) (2)(12) ring motifs. Compound (II) was refined as an inversion twin. |
format | Online Article Text |
id | pubmed-5730317 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-57303172017-12-15 Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole Dhanalakshmi, G. Saravanan, Velu Mohanakrishnan, Arasambattu K. Aravindhan, S. Acta Crystallogr E Crystallogr Commun Research Communications In the title indole derivatives, C(22)H(16)N(2)O(5)S, (I) and C(20)H(15)NO(3)S(2), (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16)°, respectively. In both compounds, the sulfonyl S atom has a distorted tetrahedral geometry [O—S—O = 119.98 (9) and N—S—C = 104.01 (8)° for compound (I) and O—S—O = 120.08 (18) and N—S—C = 104.91 (14)° for compound (II)] and the sum of the bond angles at N indicates sp (2) hybridization. The molecules of both (I) and (II) feature intramolecular C—H⋯O hydrogen bonds that generate S(6) ring motifs with the sulfone O atom. In the crystals, molecules of (I) are linked by C—H—O hydrogen bonds, forming R (4) (4)(18) ring motifs while molecules of (II) are linked by C—H—O and C—H—S hydrogen bonds, forming R (2) (2)(12) ring motifs. Compound (II) was refined as an inversion twin. International Union of Crystallography 2017-09-29 /pmc/articles/PMC5730317/ /pubmed/29250380 http://dx.doi.org/10.1107/S2056989017012804 Text en © Dhanalakshmi et al. 2017 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 Dhanalakshmi, G. Saravanan, Velu Mohanakrishnan, Arasambattu K. Aravindhan, S. Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole |
title | Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole |
title_full | Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole |
title_fullStr | Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole |
title_full_unstemmed | Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole |
title_short | Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole |
title_sort | crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1h-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1h-indole |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5730317/ https://www.ncbi.nlm.nih.gov/pubmed/29250380 http://dx.doi.org/10.1107/S2056989017012804 |
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