(E)-3-(2-Chlorophenyl)-1-(4,4′′-difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one

The title compound, C28H19ClF2O2, is a polysubstituted terphenyl derivative bearing a Michael system in which the C=C double bond has an E conformation. In the crystal, C—H⋯Cl and C—H⋯O contacts connect the molecules into layers lying perpendicular to the a axis. The shortest intercentroid distance between symmetry-related 4-fluorophenyl groups is 3.7547 (16) Å.

The title compound, C 28 H 19 ClF 2 O 2 , is a polysubstituted terphenyl derivative bearing a Michael system in which the C C double bond has an E conformation. In the crystal, C-HÁ Á ÁCl and C-HÁ Á ÁO contacts connect the molecules into layers lying perpendicular to the a axis. The shortest intercentroid distance between symmetry-related 4-fluorophenyl groups is 3.7547 (16) Å .
Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009  Terphenyl derivatives exhibit a considerable range of biological activities and show anticoagulant, immunosuppressant, antithrombotic, neuroprotective, specific 5-lipoxygenase inhibitory and cytotoxic activity effects (Liu, 2006). Due to their promising biological activities terphenyls have received increasing research interest. Therefore, synthesis of polysubstituted aromatics has been a fascinating area in the field of organic chemistry (Astrue, 2002). The molecular and crystal structures of several terphenyl derivatives (Samshuddin et al., 2011;Betz et al., 2011a,b,c,d,e) have already been reported. In view of the importance of these derivatives, the title compound was prepared and its molecular and crystal structure is reported.
In the crystal, two different C-H···Cl contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating are observed ( Fig. 2 and Table 1). These are supported by two different hydrogen atoms of the terphenyl moiety. Apart from these, a C-H···O contact involving a hydrogen atom from one of the para-fluoro phenyl ring (C41-C46) and the ketonic oxygen atom O1 is apparent ( Fig. 2 and Table 1). In terms of graph-set analysis (Etter et al., 1990;Bernstein et al., 1995), the descriptor for the C-H···F contacts is C 1 1 (10)C 1 1 (12) on the unary level while the C-H···O contacts necessitate a C 1 1 (10) descriptor on the same level. In total, the molecules are connected to form layers lying perpendicular to the a axis (Fig. 3).
Single crystals were grown from DMF by slow evaporation at room temperature. The yield of the title compound was 81% (m.p.: 452 K).

Refinement
Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation: C-H = 0.95 Å for aromatic and vinylic H atoms and 0.98 Å for methyl H atoms, with U iso (H) = k × U eq (C), where k = 1.5 for methyl H atoms and = 1.2 for other H atoms. The CH 3 H atoms were allowed to rotate with a fixed angle around the C-C bond to best fit the experimental electron density (HFIX 137 in the SHELXL; Sheldrick, 2008).