2-(4-Bromophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole

The title compound, C26H25BrN2, is isomorphous with the chloro derivative [2-(4-chlorophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole; Mohamed et al. (2013 ▶). Acta Cryst. E69, o846–o847]. The two phenyl rings and the 4-bromophenyl ring are oriented at dihedral angles of 30.1 (2), 64.3 (3) and 42.0 (2)°, respectively, with respect to the imidazole ring. In the crystal, molecules stack in columns along the b-axis direction, however, there are no significant intermolecular interactions present.


Comment
Many substituted imidazoles exhibit diverse pharmaceutical properties and are known inhibitors of fungicides and herbicides, plant growth regulators and therapeutic agents (Maier et al., 1989a,b). Moreover, they are of interest for environmental and green chemistry applications, and have been prepared and used as a large class of ionic liquids and Lewis base catalysts (Welton, 1999;Hermann & Kocher, 1997). As part of our ongoing study of the synthesis (Akkurt et al., 2013;Mohamed et al., 2013;Simpson et al., 2013) and biological applications of tetrasubstituted imidazoles, we herein report on the synthesize and crystal structure of the title compound.
The title compound, Fig. 1, and the chloro derivative, 2-(4-Chlorophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole, whose crystal structure has been reported by (Mohamed et al., 2013), are isomorphous. In the title compound the phenyl rings In the crystal, the molecules stack in columns along the b axis direction however, there are no significant intermolecular interactions present (Fig. 2).

Experimental
The title compound was synthesized following our previously reported procedure (Mohamed et al., 2013). Colourless plates of the title compound (M.p. 396-398 K) were collected with 84% yield. Crystals of sufficient quality for the X-ray diffraction study were obtained by slow evaporation of an ethanol solution of the title compound.

Refinement
All H atoms were placed in geometrically idealized positions with C-H = 0.95 -0.99 Å and refined using a riding model with U iso (H) = 1.5U eq (C-methyl) and = 1.2U eq (C) for other H atoms. The R int value is rather high probably due to the fact that the crystal diffracted weakly beyond 22° in θ. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
The crystal packing of the title compound, viewed along the b axis.  where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.61 e Å −3 Δρ min = −1.05 e Å −3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.