Received 11 June 2010
In the title compound, C17H16ClNO3, the 4-hydroxy-3-methoxybenzyl group is planar [maximum atomic deviation = 0.0138 (16) Å] and is nearly perpendicular to the chlorobenzene ring, making a dihedral angle of 84.67 (4)°. The chlorobenzene and amide groups are located on the opposite sides of the C=C bond, showing an E configuration. The relatively long C=O bond distance of 1.2364 (19) Å and the short C-N bond distance of 1.341 (2) Å suggest electron delocalization in the amide fragment. Intermolecular O-HO, N-HO and weak C-HO hydrogen bonding is present in the crystal structure.
The title compound is a derivative of capsaicin. For the biological activity of capsaicin, see: Kaga et al. (1989). For a related structure, see: Huang et al. (2010). For electron delocalization in amide groups, see: Xia et al. (2009).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2783 ).
The work was supported by the Natural Science Foundation of Zhejiang Province, China (No. M203027).
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