Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 3 (March 2013)

organic compounds

Acta Cryst. (2013). E69, o332    [ doi:10.1107/S1600536813002201 ]

N-[(1,3-Benzodioxol-5-yl)meth­yl]-4-methyl­benzamide: an analogue of capsaicin

S. H. Maganhi, M. C. F. C. B. Damião, M. T. Tavares and R. Parise Filho

Abstract: 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-H...O hydrogen bonds. These chains are connected into a layer in the ac plane by C-H...[pi] inter­actions.

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