Research Article: N-(3,4-Difluoro­phen­yl)-2,2-diphenyl­acetamide

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Hoong-Kun Fun, Chin Wei Ooi, Prakash S. Nayak, B. Narayana, B. K. Sarojini.


In the title compound, C20H15F2NO, the mean plane of the acetamide group makes dihedral angles of 88.26 (6), 78.30 (7) and 9.83 (6)° with the two terminal benzene rings and difluoro-substituted benzene ring, respectively. One F atom is disordered over two orientations rotated by 180°, with a site-occupancy ratio of 0.557 (2):0.443 (2). An intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked via N—H⋯O hydrogen bonds into chains along the c axis. The crystal structure is further consolidated by C—H⋯π inter­actions.

Partial Text

For the structural similarity of N-substituted 2-aryl­acetamides to the lateral chain of natural benzyl­penicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For the coordination abilities of amides, see: Wu et al. (2008 ▶, 2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Praveen et al. (2011a ▶,b ▶,c ▶); Fun et al. (2011a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).