N-(2-Oxo-2H-chromen-3-yl)cyclohexanecarboxamide

Abstract

In the title compound, C16H17NO3, the coumarin moiety is essentially planar [maximum deviation from the mean plane formed by the C and O atoms of the coumarin = 0.0183 (12) Å] and that the cyclohexane ring adopts the usual chair conformation. The dihedral angle between the mean plane of the coumarin residue and the plane of the amide residue (defined as the N, C and O atoms) is 18.9 (2)°. There are two intramolecular hydrogen bonds involving the amide group. In one, the N atom acts as donor to the ketonic O atom and in the other, the amide O atom acts as acceptor of a C—H group of the coumarin. In the crystal, molecules are linked into inversion dimers by pairs of N—H...O contacts and these dimers are linked into pairs by weak C—H...O hydrogen bonds. The combination of these interactions creates a chain of rings which runs parallel to [2-10]. C—H...π and π–π [centroid–centroid distance = 3.8654 (10) Å] interactions are also observed.