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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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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. |
format | Online Article Text |
id | pubmed-3379212 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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