N-(4,4′-Dibromo-[1,1′-biphenyl]-2-yl)benzamide

In the title compound, C19H13Br2NO, the dihedral angle between the rings of the biphenyl group is 53.59 (14)°. The ring of the benzamide group is inclined to the phenyl rings of the biphenyl group by 23.87 (15) and 75.89 (15)°. There are no significant intermolecular interactions in the crystal structure.

In the title compound, C 19 H 13 Br 2 NO, the dihedral angle between the rings of the biphenyl group is 53.59 (14) . The ring of the benzamide group is inclined to the phenyl rings of the biphenyl group by 23.87 (15) and 75.89 (15) . There are no significant intermolecular interactions in the crystal structure. Experimental Crystal data C 19 H 13 Br 2 NO M r = 431.12 Monoclinic, P2 1 =c a = 9.0188 (5) Å b = 11.6415 (9) Å c = 16.0068 (12)  Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009). substituted biphenyl derivatives are commonly used to develop antiparasitic agents for the treatment of African sleeping sickness disease (Libman & Slack, 1951;Mandadapu et al., 2009;Youn & Bihn, 2009;Yulan et al., 2010). Benzamides are recognized as one of the important bioactive skeletons and exhibit various potent pharmaceutical activities. As part of our studies on the substituent effects on the structures and other aspects of dibromo biphenyl derivatives, 4,4′-Dibromo-2nitrobiphenyl (Novina et al., 2012), in the present work we report herein on the synthesis and crystal structure of the title compound.
In the crystal, there are no significant interactions and the structure is stabilized by Van der Waals interactions (Fig. 2).

Experimental
To a dry THF solution of 4,4′-dibromo-[1,1′-biphenyl]-2-amine (3.27 g, 10 mmol) and triethylamine (3 ml) was added drop wise a dry THF solution (40 ml) of benzoyl chloride at 273 K. After stirring at room temperature for 20 h, the solution was poured into water (80 ml) and extracted with dichloromethane (2 × 50 ml). The combined organic extracts were dried over anhydrous Na 2 SO 4 and evaporated to dryness. This gave white solid which was further recrystallized

Figure 1
The molecular structure of the title molecule, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.  Crystal packing of the title compound viewed along the b axis.

N-(4,4′-Dibromo-[1,1′-biphenyl]-2-yl)benzamide
Crystal data  165.1, 136.0, 135.8, 134.1, 133.7, 32.6, 131.1, 130.8, 130.2, 130.1, 129.0, 128.5, 127.7, 126.8, 124.6, 122.9, 122.7. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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