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N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin
In the title compound, C(16)H(15)NO(3), the five-membered 1,3-dioxole ring is in an envelope conformation with the methylene C atom as the flap atom [lying 0.202 (3) Å out of the plane formed by the other four atoms]. The benzene ring makes a dihedral angle of 84.65 (4)° with the best least-squares...
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/PMC3588503/ https://www.ncbi.nlm.nih.gov/pubmed/23476527 http://dx.doi.org/10.1107/S1600536813002201 |
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author | Maganhi, Stella H. Damião, Mariana C. F. C. B. Tavares, Maurício T. Parise Filho, Roberto |
author_facet | Maganhi, Stella H. Damião, Mariana C. F. C. B. Tavares, Maurício T. Parise Filho, Roberto |
author_sort | Maganhi, Stella H. |
collection | PubMed |
description | In the title compound, C(16)H(15)NO(3), the five-membered 1,3-dioxole ring is in an envelope conformation with the methylene C atom as the flap atom [lying 0.202 (3) Å out of the plane formed by the other four atoms]. The benzene ring makes a dihedral angle of 84.65 (4)° with the best least-squares plane through the 1,3-benzodioxole fused-ring system, which substitutes the 2-methoxyphenol moiety in capsaicin. In the crystal, molecules are connected into a zigzag supramolecular chain along the c-axis direction by N—H⋯O hydrogen bonds. These chains are connected into a layer in the ac plane by C—H⋯π interactions. |
format | Online Article Text |
id | pubmed-3588503 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-35885032013-03-08 N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin Maganhi, Stella H. Damião, Mariana C. F. C. B. Tavares, Maurício T. Parise Filho, Roberto Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(16)H(15)NO(3), the five-membered 1,3-dioxole ring is in an envelope conformation with the methylene C atom as the flap atom [lying 0.202 (3) Å out of the plane formed by the other four atoms]. The benzene ring makes a dihedral angle of 84.65 (4)° with the best least-squares plane through the 1,3-benzodioxole fused-ring system, which substitutes the 2-methoxyphenol moiety in capsaicin. In the crystal, molecules are connected into a zigzag supramolecular chain along the c-axis direction by N—H⋯O hydrogen bonds. These chains are connected into a layer in the ac plane by C—H⋯π interactions. International Union of Crystallography 2013-02-02 /pmc/articles/PMC3588503/ /pubmed/23476527 http://dx.doi.org/10.1107/S1600536813002201 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. Damião, Mariana C. F. C. B. Tavares, Maurício T. Parise Filho, Roberto N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin |
title |
N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin |
title_full |
N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin |
title_fullStr |
N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin |
title_full_unstemmed |
N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin |
title_short |
N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin |
title_sort | n-[(1,3-benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588503/ https://www.ncbi.nlm.nih.gov/pubmed/23476527 http://dx.doi.org/10.1107/S1600536813002201 |
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