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N-Hexyl-3-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)propanamide

In the title compound, C(17)H(27)NO(4), which is an hydro­sinapic acid derivative with increased lipophilicity conferred by an additional alkyl chain, the central and the hexyl linear chains contain slightly shorter bond lengths [C—N = 1.316 (2) Å; average linear chain C—C = 1.487 (6) Å] than report...

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Autores principales: Andrade, L. C. R., Paixão, J. A., de Almeida, M. J. M., Tavares da Silva, E. J., Fernandes Roleira, F. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379212/
https://www.ncbi.nlm.nih.gov/pubmed/22719410
http://dx.doi.org/10.1107/S1600536812019022
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author Andrade, L. C. R.
Paixão, J. A.
de Almeida, M. J. M.
Tavares da Silva, E. J.
Fernandes Roleira, F. M.
author_facet Andrade, L. C. R.
Paixão, J. A.
de Almeida, M. J. M.
Tavares da Silva, E. J.
Fernandes Roleira, F. M.
author_sort Andrade, L. C. R.
collection PubMed
description In the title compound, C(17)H(27)NO(4), which is an hydro­sinapic acid derivative with increased lipophilicity conferred by an additional alkyl chain, the central and the hexyl linear chains contain slightly shorter bond lengths [C—N = 1.316 (2) Å; average linear chain C—C = 1.487 (6) Å] than reported average values [Csp (2)—N = 1.334, C—C for CH(2)—CH(2) = 1.524 and 1.513 Å for CH(2)—CH(3)]. The 4-hy­droxy-3,5-dimeth­oxy­phenyl plane [r.m.s. deviation 0.055 (12) Å] makes an angle of 59.89 (5)° with the central plane of the mol­ecule (composed of the N atom, the carbonyl group and the two methyl­ene C atoms linking the carbonyl group and the ring, [r.m.s. deviation 0.0026 (10) Å], which, in turn, makes an angle of 64.24 (13)° with the essentially planar hexyl chain [r.m.s. deviation 0.035 (18) Å]. The N—H group of the amide group is involved in a bifurcated hydrogen bond towards the hy­droxy and one of the meth­oxy O atoms of the 4-hy­droxy-3,5-dimeth­oxy­phenyl substituent of a neighbouring mol­ecule, forming a two-dimensional network in the (100) plane. In addition, the same hy­droxy group acts as a donor towards the carbonyl O atom of another neighbouring mol­ecule, forming chains running along the b axis.
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spelling pubmed-33792122012-06-20 N-Hexyl-3-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)propanamide Andrade, L. C. R. Paixão, J. A. de Almeida, M. J. M. Tavares da Silva, E. J. Fernandes Roleira, F. M. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(17)H(27)NO(4), which is an hydro­sinapic acid derivative with increased lipophilicity conferred by an additional alkyl chain, the central and the hexyl linear chains contain slightly shorter bond lengths [C—N = 1.316 (2) Å; average linear chain C—C = 1.487 (6) Å] than reported average values [Csp (2)—N = 1.334, C—C for CH(2)—CH(2) = 1.524 and 1.513 Å for CH(2)—CH(3)]. The 4-hy­droxy-3,5-dimeth­oxy­phenyl plane [r.m.s. deviation 0.055 (12) Å] makes an angle of 59.89 (5)° with the central plane of the mol­ecule (composed of the N atom, the carbonyl group and the two methyl­ene C atoms linking the carbonyl group and the ring, [r.m.s. deviation 0.0026 (10) Å], which, in turn, makes an angle of 64.24 (13)° with the essentially planar hexyl chain [r.m.s. deviation 0.035 (18) Å]. The N—H group of the amide group is involved in a bifurcated hydrogen bond towards the hy­droxy and one of the meth­oxy O atoms of the 4-hy­droxy-3,5-dimeth­oxy­phenyl substituent of a neighbouring mol­ecule, forming a two-dimensional network in the (100) plane. In addition, the same hy­droxy group acts as a donor towards the carbonyl O atom of another neighbouring mol­ecule, forming chains running along the b axis. International Union of Crystallography 2012-05-02 /pmc/articles/PMC3379212/ /pubmed/22719410 http://dx.doi.org/10.1107/S1600536812019022 Text en © Andrade et al. 2012 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
Andrade, L. C. R.
Paixão, J. A.
de Almeida, M. J. M.
Tavares da Silva, E. J.
Fernandes Roleira, F. M.
N-Hexyl-3-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)propanamide
title N-Hexyl-3-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)propanamide
title_full N-Hexyl-3-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)propanamide
title_fullStr N-Hexyl-3-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)propanamide
title_full_unstemmed N-Hexyl-3-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)propanamide
title_short N-Hexyl-3-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)propanamide
title_sort n-hexyl-3-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)propanamide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379212/
https://www.ncbi.nlm.nih.gov/pubmed/22719410
http://dx.doi.org/10.1107/S1600536812019022
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