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

ABSTRACT: 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?? inter-actions.

SUBMITTER: Maganhi SH 

PROVIDER: S-EPMC3588503 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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

Maganhi Stella H SH   Damião Mariana C F C B MC   Tavares Maurício T MT   Parise Filho Roberto R  

Acta crystallographica. Section E, Structure reports online 20130202 Pt 3

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-axi  ...[more]

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