Research Article: 3-(4-Chloro­anilino)-2,5-dimethyl­cyclo­hex-2-en-1-one

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.

Partial Text

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 ▶).




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