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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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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. |
format | Online Article Text |
id | pubmed-3200696 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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