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

In the title compound, C28H19BrF2O2, the central benzene ring makes dihedral angles of 62.51 (18), 46.23 (18) and 48.19 (18)° with the bromo-substituted benzene ring and two terminal fluoro-substituted benzene rings, respectively. In the crystal, molecules are linked by C—H⋯F hydrogen bonds into infinite chains along [110]. Weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.683 (2) Å] also occur and short intermolecular F⋯F contacts [2.833 (4) Å] are observed.


Related literature
For related structures and background to terphenyl chalcones, see: Fun et al. (2011aFun et al. ( ,b, 2012. For reference bond lengths, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 Table 1 Hydrogen-bond geometry (Å , ).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009  In continuation of our work on the synthesis and structures of terphenyl chalcones (Fun et al., 2011a,b), the title compound (I) is now described. The starting material of the title compound was prepared from 4,4′-difluoro chalcone by several steps (Fun et al., 2012).
Colourless needles were grown from DMF solution by slow evaporation method and yield of the compound was 79%.

Refinement
All H atoms were positioned geometrically [C-H = 0.93 and 0.96 Å] and refined using a riding model with U iso (H) = 1.2 or 1.5U eq (C). A rotating group model was applied to the methyl group.

Computing details
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009  The molecular structure of the title compound with 50% probability displacement ellipsoids.  The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.  (Cosier & Glazer, 1986) operating at 100.0 (1) K. 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.