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Acta Crystallogr Sect E Struct Rep Online. 2013 Mar 1;69(Pt 3):o332. doi: 10.1107/S1600536813002201. Epub 2013 Feb 2.

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

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Departmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil.


In the title compound, C16H15NO3, the five-membered 1,3-dioxole ring is in an envelope conformation with the methyl-ene 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, mol-ecules are connected into a zigzag supra-molecular 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 inter-actions.

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