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

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...π interactions.