Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 11 (November 2013)


organic compounds



tk5268 scheme

Acta Cryst. (2013). E69, o1700    [ doi:10.1107/S1600536813028481 ]

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

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

Abstract: The title compound, C14H13NO4S, an analogue of capsaicin, differs from the latter by having a 1,3-benzodioxole ring rather than a 2-meth­oxy­phenol moiety, and having a benzene­sulfonamide group instead of an aliphatic amide chain. The five-membered ring is in an envelope conformation with the methyl­ene C atom lying 0.221 (6) Å out of the plane formed by the other four atoms. The dihedral angle between the phenyl ring and the mean plane of the 1,3-benzodioxole fused-ring system is 84.65 (4)°. In the crystal, mol­ecules aggregate into supra­molecular layers in the ac plane through C-H...O, N-H...O and C-H...[pi] inter­actions.


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