Research Article: Evodiamide

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): Fang Cai, Jie Wu, Hai-Yan Tian, Xiao-Feng Yuan, Ren-Wang Jiang.


The title compound, C19H21N3O, was isolated from the fruits of Evodia rutaecarpa. The indole and benzene rings are both essentially planar with mean derivations of 0.0094 (4) Å and 0.0077 (3) Å, respectively. The dihedral angle between these two planes is 78.24 (9)°. The amide carbonyl plane is roughly parallel to the indole ring with a dihedral angle of 7.0 (2)°, but makes a dihedral angle of 82.9 (3)° with the benzene ring. Inter­molecular N—H⋯O hydrogen-bonding inter­actions involving the amino and carbonyl groups give rise to a three-dimensional network.

Partial Text

For previous isolation of evodiamide, see: Shoji et al. (1988 ▶); Tang et al. (1997 ▶); Zuo et al. (2003 ▶). For the LC–MS analysis, see: Zhou et al. (2006 ▶). For the crystal structure of evodiamine, see: Fujii et al. (2000 ▶). For the biological activity of Evodia rutaecarpa and related alkaloids, see: Liao et al. (2011 ▶).