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2-(Phenyl­amino­methyl­idene)­cyclo­hexane-1,3-dione

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Abstract:

In the title compound, C13H13NO2, there is polarization of -electron density from the amine N atom to the acceptor carbonyl groups: as a result, the mol­ecule exists predominantly in an azomethino-1,3-diketone tautomeric form. There is crystallographic evidence that the phenyl ring, although roughly coplanar with the rest of the mol­ecule, is deconjugated with the adjacent  system of the mol­ecule. The cyclo­hexane ring adopts an unsymmetrical half-chair conformation and converts between two inversion-related conformers. The mol­ecule is stabilized by an intramolecular hydrogen bond, while the intermolecular packing is dominated by a number of short C—H…O contacts.

Document Type: Research Article

DOI: http://dx.doi.org/10.1107/S0108270104003610

Publication date: April 1, 2004

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