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

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 coumari...

Full description

Bibliographic Details
Main Authors: Matos, Maria J., Santana, Lourdes, Uriarte, Eugenio
Format: Online
Language:English
Published: International Union of Crystallography 2012
Online Access:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3589025/
Description
Summary: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.