Date Published: August 01, 2009
Publisher: International Union of Crystallography
Author(s): Liang-You Xia, Wen-Long Wang, Shan-Heng Wang, Yan-Lan Huang, Shang Shan.
In the molecular structure of the title compound, C15H15NO3, the two benzene rings are twisted with respect to each other, making a dihedral angle of 75.11 (10)°. In the amide fragment, the C=O and C—N bond distances are 1.248 (3) and 1.321 (3) Å, respectively, indicating electron delocalization. A partially ovelapped arrangement between parallel hydroxymethoxybenzene rings is observed in the crystal structure, and the face-to-face distance of 3.531 (16) Å suggests the existence of weak π–π stacking. N—H⋯O and O—H⋯O hydrogen bonding is also present in the crystal structure.
The title compound was obtained during an investigation of capsaicin and its derivatives. For the biological activity of capsaicin, see: Kaga et al. (1989 ▶). For related structures, see: Luo & Huang (2004 ▶); Tong et al. (2008 ▶).