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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...

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Autores principales: Maganhi, Stella H., Damião, Mariana C. F. C. B., Tavares, Maurício T., Parise Filho, Roberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
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.
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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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