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2-Azido­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole

In the title compound, C(16)H(14)N(4)O(2)S, the plane of the indole ring is twisted by 70.4 (2)° with respect to the plane of the azidomethyl­ substituent. As a result of the electron-withdrawing character of the phenyl­sulfonyl groups, the N—C bond lengths are slightly longer than the anti­cipated...

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Autores principales: Karthikeyan, S., Sethusankar, K., Rajeswaran, Ganesan Gobi, Mohanakrishnan, Arasambattu K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3200696/
https://www.ncbi.nlm.nih.gov/pubmed/22065043
http://dx.doi.org/10.1107/S1600536811030601
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author Karthikeyan, S.
Sethusankar, K.
Rajeswaran, Ganesan Gobi
Mohanakrishnan, Arasambattu K.
author_facet Karthikeyan, S.
Sethusankar, K.
Rajeswaran, Ganesan Gobi
Mohanakrishnan, Arasambattu K.
author_sort Karthikeyan, S.
collection PubMed
description In the title compound, C(16)H(14)N(4)O(2)S, the plane of the indole ring is twisted by 70.4 (2)° with respect to the plane of the azidomethyl­ substituent. As a result of the electron-withdrawing character of the phenyl­sulfonyl groups, the N—C bond lengths are slightly longer than the anti­cipated value of approximately 1.355 Å for an N atom with a planar configuration. The indole ring is essentially planar, with a maximum deviation of 0.0296 Å. The azide group is almost linear, the N—N—N angle being 171.4 (3)°. The methyl group on the azide-substituted C atom is in a flagpole position. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 87.07 (10)° with the best plane of the indole moiety. The crystal packing is stabilized by inter­molecular C—H⋯O inter­actions, which link the mol­ecules into infinite chains running parallel to the b axis. The crystal packing is further stabilized by C—H⋯π inter­actions.
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spelling pubmed-32006962011-11-06 2-Azido­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole Karthikeyan, S. Sethusankar, K. Rajeswaran, Ganesan Gobi Mohanakrishnan, Arasambattu K. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(16)H(14)N(4)O(2)S, the plane of the indole ring is twisted by 70.4 (2)° with respect to the plane of the azidomethyl­ substituent. As a result of the electron-withdrawing character of the phenyl­sulfonyl groups, the N—C bond lengths are slightly longer than the anti­cipated value of approximately 1.355 Å for an N atom with a planar configuration. The indole ring is essentially planar, with a maximum deviation of 0.0296 Å. The azide group is almost linear, the N—N—N angle being 171.4 (3)°. The methyl group on the azide-substituted C atom is in a flagpole position. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 87.07 (10)° with the best plane of the indole moiety. The crystal packing is stabilized by inter­molecular C—H⋯O inter­actions, which link the mol­ecules into infinite chains running parallel to the b axis. The crystal packing is further stabilized by C—H⋯π inter­actions. International Union of Crystallography 2011-08-06 /pmc/articles/PMC3200696/ /pubmed/22065043 http://dx.doi.org/10.1107/S1600536811030601 Text en © Karthikeyan et al. 2011 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 Organic Papers
Karthikeyan, S.
Sethusankar, K.
Rajeswaran, Ganesan Gobi
Mohanakrishnan, Arasambattu K.
2-Azido­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole
title 2-Azido­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole
title_full 2-Azido­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole
title_fullStr 2-Azido­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole
title_full_unstemmed 2-Azido­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole
title_short 2-Azido­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole
title_sort 2-azido­methyl-3-methyl-1-phenyl­sulfonyl-1h-indole
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3200696/
https://www.ncbi.nlm.nih.gov/pubmed/22065043
http://dx.doi.org/10.1107/S1600536811030601
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