(E)-N-Butyl-3-(3,4-dihy-droxy-phen-yl)acryl-amide hemihydrate.

ABSTRACT: In the title compound, C(13)H(17)NO(3)·0.5H(2)O, a new caffeic acid amide derivative, the solvent water mol-ecule lies on a twofold axis and the terminal ethyl group appears disordered with occupancy factors of 0.525?(6) and 0.475?(6). The benzene ring makes an angle of 17.3?(2)° with the C=C-C-O linker. The presence of an ethyl-enic spacer in the caffeic acid amide mol-ecule allows the formation of a conjugated system, strongly stabilized through ?-electron delocalization. The C=C double bond in the linker is trans, similar to those previously reported in caffeic esters. The crystal is stabilized by O-H?O, N-H?O and C-H?O hydrogen bonds. The mol-ecules of the caffeic acid amide form a supermolecular planar structure through O-H?O hydrogen bonds between a hy-droxy group of one caffeic acid mol-ecule and a carbonyl O atom of another. These planes inter-act via C-H?O, O-H?O and N-H?O hydrogen bonds to form a three-dimensional network.

SUBMITTER: Han Y 

PROVIDER: S-EPMC3295498 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature