Received 21 January 2013
In the title compound, C16H15NO3, the five-membered 1,3-dioxole ring is in an envelope conformation with the methylene C atom as the flap atom [lying 0.202 (3) Å out of the plane formed by the other four atoms]. The benzene ring makes a dihedral angle of 84.65 (4)° with the best least-squares plane through the 1,3-benzodioxole fused-ring system, which substitutes the 2-methoxyphenol moiety in capsaicin. In the crystal, molecules are connected into a zigzag supramolecular chain along the c-axis direction by N-HO hydrogen bonds. These chains are connected into a layer in the ac plane by C-H interactions.
For the biological activity of capsaicin, see: Okamoto et al. (2011). For ring conformational analysis, see: Cremer & Pople (1975).
Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Marvinsketch (Chemaxon, 2010) and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5191 ).
We thank the Brazilian agencies CNPq (140925/2009-0 to SHM), FAPESP and CAPES for financial support. We also thank Professor Carlos A. De Simone for the data collection.
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