3-(4-Chlorobenzoyl)-6-(4-chlorophenyl)-2,4-dimethylbenzonitrile

In the title compound, C22H15Cl2NO, the terminal chlorobenzene rings are oriented at 44.51 (15) and 86.06 (17)° with respect to the central polysubstituted benzene ring, and make a dihedral angle of 49.48 (17)°with each other. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯N interactions.

In the title compound, C 22 H 15 Cl 2 NO, the terminal chlorobenzene rings are oriented at 44.51 (15) and 86.06 (17) with respect to the central polysubstituted benzene ring, and make a dihedral angle of 49.48 (17) with each other. In the crystal, molecules are linked by weak C-HÁ Á ÁO and C-HÁ Á ÁN interactions.
supplementary materials Acta Cryst. (2012). E68, o2787 [doi:10.1107/S1600536812036409] 3-(4-Chlorobenzoyl)-6-(4-chlorophenyl)-2,4-dimethylbenzonitrile Xin Wang, Yi-Min Zhang and Xue-Fei Jia Comment It has been well documented that benzenoid compounds are ubiquitous structural units in a wide variety of naturally occurring compounds and a plethora of pharmaceuticals. On the other hand, allene derivatives are powerful synthetic intermediates toward a plethora of important organic compounds and frequent building blocks of natural products (Ma, 2003(Ma, , 2005(Ma, , 2007Hoffmann-Röder et al., 2004). In this regard, Zhang et al. have developed a novel and efficient method for the preparation of polysubstituted benzenes by one-pot double Michael addition/intramolecular aldol reaction/ decarboxylation of 1,2-allenic ketones with cyanoacetate (Zhang et al., 2011). Herein, we would like to report the structure of one of the products obtained by this method.
In the crystal structure, the molecules are connected via C-H···O and C-H···N interactions.

Experimental
A mixture of 1-(4-chlorophenyl)buta-2,3-dien-1-one (1 mmol), cyanoacetate (0.5 mmol) and K 2 CO 3 (0.5 mmol) in acetone (5 ml) was refluxed for 15 min. Upon completion, the reaction mixture was cooled to room temperature, added with water (10 ml) and extracted with ethyl acetate. The combined organic phases were washed with brine, dried, filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (1:20 v/v) to give the title compound as Colorless solids with a yield of 80%. Single crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of solvent from a petroleum ether-dichloromethane (2:1 v/v) solution.

Refinement
The H atoms were included at calculated positions and were refined as riding atoms: C-H = 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, with U iso (H) =xU eq (C), where x = 1.2 for aromatic H, and x = 1.5 for methyl H atoms.    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.