1-(4-Bromophenyl)-2-(2-chlorophenoxy)ethanone

In the title compound, C14H10BrClO2, a twofold halogenated derivative of phenylated phenyloxyethanone, the least-squares planes defined by the C atoms of the aromatic rings subtend an angle of 71.31 (17)°. In the crystal, C—H⋯O contacts connect the molecules into chains along the b-axis direction.

In the title compound, C 14 H 10 BrClO 2 , a twofold halogenated derivative of phenylated phenyloxyethanone, the leastsquares planes defined by the C atoms of the aromatic rings subtend an angle of 71.31 (17) . In the crystal, C-HÁ Á ÁO contacts connect the molecules into chains along the b-axis direction.   Table 1 Hydrogen-bond geometry (Å , ).  antibacterial (Iqbal et al., 2007), analgesic (Sato et al., 2002), diuretic (Kitagawa et al., 1991Bicking et al., 1976) and growth regulatory (Osborne et al., 1955) activity. In continuation of our ongoing interest in bioactive compounds, the title compound was synthesized and its crystal structure was determined.

Related literature
The O-C-C-O dihedral angle is found at -0.8 (4) °. A statistics of values for dihedral angles of comparable compounds whose molecular and crystal structure has been deposited with the CSD (Allen, 2002) shows that this eclipsed conformation is considerably smaller than the average angle found for the majority of these compounds. The leastsquares planes defined by the carbon atoms of the two aromatic moieties enclose an angle of 71.31 (17) ° ( Fig. 1 and Fig.   2).
In the crystal, intermolecular C-H···O contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating are apparent. These are supported by one of the hydrogen atoms of the methylene group as well as the hydrogen atom in ortho position to the oxygen atom on the chlorophenyl moiety as donors and have the ketonic oxygen atom as acceptor. These connect the molecules to chains along the crystallographic b axis. Information about metrical parameters as well as the symmetry of these contacts is summarized in Table 1. In terms of graph-set analysis (Etter et al., 1990;Bernstein et al., 1995), the descriptor for these contacts is C 1 1 (4)C 1 1 (7) on the unary level. In addition, a dispersive Br···Br contact (3.583 (5) Å) was detected. The shortest intercentroid distance between two aromatic systems was measured at 4.554 (2) Å and is present between the chlorinated phenyl moiety and its symmetrygenerated equivalent as well as between the brominated phenyl moiety and its symmetry-generated equivalent (Fig. 3).
This value is in agreement with the length of cell axis b.
The packing of the title compound in the crystal structure is shown in Figure 4.

Refinement
Carbon-bound H atoms were placed in calculated positions (C-H 0.95 Å for aromatic carbon atoms and C-H 0.99 Å for methylene groups) and were included in the refinement in the riding model approximation, with U iso (H) set to 1.2U eq (C).

Figure 1
The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).