Date Published: May 01, 2009
Publisher: International Union of Crystallography
Author(s): B. Thimme Gowda, Miroslav Tokarčík, Jozef Kožíšek, B. P. Sowmya, Hartmut Fuess.
The conformation of the N—H bond in the structure of the title compound, C15H15NO, is anti to the ortho and meta-methyl substituents in the aniline benzene ring, in contrast to the syn conformation observed with respect to the ortho and meta-chloro substituents in N-(2,3-dichlorophenyl)benzamide. Furthermore, the conformations of N—H and C=O bonds in the amide group are anti to each other, similar to those observed in other benzanilides. The dihedral angle between the benzoyl and aniline rings is 84.1 (2)°. The amide group is twisted by 23.0 (3)° out of the plane of the benzoyl ring. The structure exhibits positional disorder over the aniline ring, with site occupancies of 0.80 (1) and 0.20 (1) for the major and minor components, respectively. In the crystal, molecules are connected through N—H⋯O hydrogen bonds into chains running along the b axis. An intramolecular C—H⋯O close contact occurs.
For related structures, see Azumaya et al. (1994 ▶); Gowda et al. (2003 ▶, 2007 ▶, 2008a ▶,b ▶).