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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...

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Autores principales: Dhanalakshmi, G., Saravanan, Velu, Mohanakrishnan, Arasambattu K., Aravindhan, S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
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.
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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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