Date Published: May 01, 2011
Publisher: International Union of Crystallography
Author(s): Henry North, Kwame Wutoh, M’egya K. Odoom, Pradeep Karla, Kenneth R. Scott, Ray J. Butcher.
In the title compound, C14H16ClNO, the dihedral angle between the benzene ring and the conjugated part of the cyclohexene ring is 61.7 (2)°. Part of the cyclohexene ring and one of the attached methyl groups are disordered over two orientations with occupancies of 0.602 (7) and 0.398 (7). In addition, the crystal studied was a racemic twin [Flack parameter = 0.58 (4)]. In the crystal, the molecules are linked into chains in the b-axis direction by intermolecular N—H⋯O hydrogen bonds. C—H⋯O and C—H⋯Cl interactions are also observed.
The title compound 3-(4-chlorophenylamino)-2,5-dimethylcyclohex-2-enone possesses significant anticonvulsant properties. For the anticonvulsant properties of enaminones, see: Edafiogho et al. (1992 ▶); Eddington et al. (2003 ▶); Scott et al. (1993 ▶, 1995 ▶). For related structures see: Alexander et al. (2010 ▶, 2011 ▶).