2-(phenylaminomethylidene)cyclohexane-1,3-dione.
In the title compound, C(13)H(13)NO(2), there is polarization of pi-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 pi 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.
Kettmann
Viktor
V
Faculty of Pharmacy, Comenius University, Odbojarov 10, Bratislava 83232, Slovak Republic. kettmann@fpharm.uniba.sk
Lokaj
Jan
J
Milata
Viktor
V
Marko
Milan
M
Stvrtecká
Magdaléna
M
D000814:Aniline Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003512:Cyclohexanones / Q000737:chemistry*; D015394:Molecular Structure; D038761:Photobleaching / Q000187:drug effects
D000814:Aniline Compounds; D003512:Cyclohexanones