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N-[(1,3-Benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin
The title compound, C(14)H(13)NO(4)S, an analogue of capsaicin, differs from the latter by having a 1,3-benzodioxole ring rather than a 2-methoxyphenol moiety, and having a benzenesulfonamide group instead of an aliphatic amide chain. The five-membered ring is in an envelope conformation with the...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3884350/ https://www.ncbi.nlm.nih.gov/pubmed/24454126 http://dx.doi.org/10.1107/S1600536813028481 |
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author | Maganhi, Stella H. Tavares, Maurício T. Damião, Mariana C. F. C. B. Parise Filho, Roberto |
author_facet | Maganhi, Stella H. Tavares, Maurício T. Damião, Mariana C. F. C. B. Parise Filho, Roberto |
author_sort | Maganhi, Stella H. |
collection | PubMed |
description | The title compound, C(14)H(13)NO(4)S, an analogue of capsaicin, differs from the latter by having a 1,3-benzodioxole ring rather than a 2-methoxyphenol moiety, and having a benzenesulfonamide group instead of an aliphatic amide chain. The five-membered ring is in an envelope conformation with the methylene C atom lying 0.221 (6) Å out of the plane formed by the other four atoms. The dihedral angle between the phenyl ring and the mean plane of the 1,3-benzodioxole fused-ring system is 84.65 (4)°. In the crystal, molecules aggregate into supramolecular layers in the ac plane through C—H⋯O, N—H⋯O and C—H⋯π interactions. |
format | Online Article Text |
id | pubmed-3884350 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-38843502014-01-17 N-[(1,3-Benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin Maganhi, Stella H. Tavares, Maurício T. Damião, Mariana C. F. C. B. Parise Filho, Roberto Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(14)H(13)NO(4)S, an analogue of capsaicin, differs from the latter by having a 1,3-benzodioxole ring rather than a 2-methoxyphenol moiety, and having a benzenesulfonamide group instead of an aliphatic amide chain. The five-membered ring is in an envelope conformation with the methylene C atom lying 0.221 (6) Å out of the plane formed by the other four atoms. The dihedral angle between the phenyl ring and the mean plane of the 1,3-benzodioxole fused-ring system is 84.65 (4)°. In the crystal, molecules aggregate into supramolecular layers in the ac plane through C—H⋯O, N—H⋯O and C—H⋯π interactions. International Union of Crystallography 2013-10-23 /pmc/articles/PMC3884350/ /pubmed/24454126 http://dx.doi.org/10.1107/S1600536813028481 Text en © Maganhi et al. 2013 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 Maganhi, Stella H. Tavares, Maurício T. Damião, Mariana C. F. C. B. Parise Filho, Roberto N-[(1,3-Benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin |
title |
N-[(1,3-Benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin |
title_full |
N-[(1,3-Benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin |
title_fullStr |
N-[(1,3-Benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin |
title_full_unstemmed |
N-[(1,3-Benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin |
title_short |
N-[(1,3-Benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin |
title_sort | n-[(1,3-benzodioxol-5-yl)methyl]benzenesulfonamide: an analogue of capsaicin |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3884350/ https://www.ncbi.nlm.nih.gov/pubmed/24454126 http://dx.doi.org/10.1107/S1600536813028481 |
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