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

Date Published: June 01, 2012

Publisher: International Union of Crystallography

Author(s): L. C. R. Andrade, J. A. Paixão, M. J. M. de Almeida, E. J. Tavares da Silva, F. M. Fernandes Roleira.


In the title compound, C17H27NO4, 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 [Csp2—N = 1.334, C—C for CH2—CH2 = 1.524 and 1.513 Å for CH2—CH3]. 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.

Partial Text

For the dependence on their structural characteristics of the anti­cancer activity of phenolic acids and their derivatives, see: Gomes et al. (2003 ▶). For restrictions on protection of lipophilic systems due to the hydro­philic nature of mol­ecules in aqueous media, see: Gao & Hu (2010 ▶). For the synthesis, see: Roleira et al. (2010 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).




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