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.
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 ▶).