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N-(2-Oxo-2H-chromen-3-yl)cyclo-hexane-carboxamide.

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 cyclo-hexane 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 intra-molecular 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, mol-ecules 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 inter-actions creates a chain of rings which runs parallel to [2-10]. C-H?? and ?-? [centroid-centroid distance = 3.8654?(10)?Å] inter-actions are also observed.

SUBMITTER: Matos MJ

PROVIDER: S-EPMC3589025 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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N-(2-Oxo-2H-chromen-3-yl)cyclo-hexane-carboxamide.

Matos Maria J MJ Santana Lourdes L Uriarte Eugenio E

Acta crystallographica. Section E, Structure reports online 20121124 Pt 12

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 cyclo-hexane 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 intra-molecular hydrogen bonds involving the amide group. In one, the N atom acts as donor to ...[more]

PMID: 23476261

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