2-(4-Chlorophenyl)-N-(3,4-difluorophenyl)acetamide

In the title compound, C14H10ClF2NO, the dihedral angle between the mean planes of the 4-chlorophenyl and 3,4-difluorophenyl rings is 65.2 (1)°. These two planes are twisted by 83.5 (5) and 38.9 (9)°, respectively, from that of the acetamide group. In the crystal, N—H⋯O hydrogen bonds form infinite chains along [100]. Weak C—H⋯O and C—H⋯F interactions are also observed and stack molecules along the b axis.

In the title compound, C 14 H 10 ClF 2 NO, the dihedral angle between the mean planes of the 4-chlorophenyl and 3,4difluorophenyl rings is 65.2 (1) . These two planes are twisted by 83.5 (5) and 38.9 (9) , respectively, from that of the acetamide group. In the crystal, N-HÁ Á ÁO hydrogen bonds form infinite chains along [100]. Weak C-HÁ Á ÁO and C-HÁ Á ÁF interactions are also observed and stack molecules along the b axis.

D-HÁ
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009). ASP thanks the University of Mysore for research facilities. BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

Refinement
All of the H atoms were placed in their calculated positions and then refined using the riding model with atom-H lengths of 0.95Å (CH), 0.99Å (CH 2 ) or 0.88° (NH). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH 2 , NH) times U eq of the parent atom. Molecular structure of the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids.

Figure 2
Packing diagram of the title compound viewed along the b axis. Dashed lines indicate N-H···O hydrogen bonds forming infinite chains along (100). H atoms not involved in hydrogen bonding have been deleted for clarity.

Figure 3
Synthesis of (I).   Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Cl1 0.07824 (