2-(4-Methoxyphenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole

The asymmetric unit of the title compound, C25H22N2O, contains two independent molecules (A and B), with significantly different conformations. In molecule A, the central imidazole ring makes dihedral angles of 88.26 (10) and 12.74 (11)° with the two phenyl rings, and 22.06 (9)° with the benzene ring. In molecule B, one of the phenyl rings is disordered over two sites, each having an occupancy of 0.5. Here the central imidazole ring forms dihedral angles of 79.24 (10)° with the ordered phenyl ring, and 3.5 (5) and 22.6 (5)° with the two parts of the disordered phenyl ring. The dihedral angle involving the benzene ring is 67.49 (10)°. The —N—C(H2)—C(H)—C(H2) torsion angles of the prop-1-ene group in the two molecules are very similar, 0.5 (3) and 1.3 (4)° for molecules A and B, respectively. The crystal structure is stabilized by C—H⋯π interactions.


Gurbanov Comment
Imidazole derivatives are a great class of heterocyclic compounds due to their wide range of pharmacological and biological activities They exhibited as inhibitors of p38 MAP kinase, fungicides, herbicides, plant growth regulators, antibacterial, antitumour, pesticides and therapeutic agents (Bhatnagar et al. (2011);Puratchikody & Doble 2007;Wang et al., 2002 andAntolini, et al., 1999). They also serve as useful building blocks for synthesis of diverse class of bioactive molecules. Further to our study on synthesis of bioactive heterocyclic molecules we herein report the crystal structure of the title compound.
The molecular structure of the two independent molecules (A and B) of the title compound are illustrated in Fig. 1 Both molecules have a similar conformation. The -N-C(H 2 )-C(H)-C(H 2 ) torsion angles of the prop-1-ene group are 0.5 (3) and 1.3 (4)° in molecules A and B, respectively. The bond lengths and angles of both molecules are comparable and similar to the values reported in the literature (Allen et al., 1987).
In the crystal, there is no classical hydrogen bonds; the molecules are linked via C-H···π interactions (Table 1 and Fig. 2).

Experimental
The title compound was prepared, among series of imidazole derivatives, according to our reported method (Mohamed et al., 2012) in 88% yield. Suitable single crystals were obtained by slow evaporation of a solution in ethanol M.p. 385-387 K.

Refinement
H atoms were positioned geometrically, C-H = 0.93 Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene) H atoms, respectively, and refined as riding with U iso (H) = 1.2U eq (C) or 1.5U eq (C) for methyl H atoms. Each atom of the disordered phenyl ring [one part C38-C43 and the other C38′-C43′] of molecule B have an occupancy of 0.5. Their displacement parameters were restrained using ISOR. The C30-C38 and C30-C38′ distances were restrained to be equal using the command SADI. Their anisotropic displacement parameters were also made equal using the EADP constraint. Two

2-(4-Methoxyphenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole
Crystal data 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.