Research Article: N-(4-Hydr­oxy-3-methoxy­benz­yl)benzamide

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.

Partial Text

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 ▶).




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