2-(4-Fluorophenyl)-1-(4-methoxyphenyl)-1H-phenanthro[9,10-d]imidazole

In the title compound, C28H19FN2O, the phenanthrene fused with an imidazole ring, constituting an essentially planar tetracyclic system [maximum deviation = 0.032 (2) Å], makes dihedral angles of 60.83 (4) and 80.55 (4)° with the fluorobenzene and methoxybenzene rings, respectively. The dihedral angle between the the methoxybenzene and fluorobenzene rings is 69.45 (6)°. In the crystal, C—H⋯O hydrogen bonds connect the molecules into infinite strands along the b axis. The crystal structure is further consolidated by C—H⋯π interactions.

In the title compound, C 28 H 19 FN 2 O, the phenanthrene fused with an imidazole ring, constituting an essentially planar tetracyclic system [maximum deviation = 0.032 (2) Å ], makes dihedral angles of 60.83 (4) and 80.55 (4) with the fluorobenzene and methoxybenzene rings, respectively. The dihedral angle between the the methoxybenzene and fluorobenzene rings is 69.45 (6) . In the crystal, C-HÁ Á ÁO hydrogen bonds connect the molecules into infinite strands along the b axis. The crystal structure is further consolidated by C-HÁ Á Á interactions.
The bond lengths and bond angles in the title compound ( Fig. 1) are normal and agree very well with the corresponding bond lengths and bond angles reported for closely related compounds (Yuan et al., 2011;Krebs et al., 2001). The tetracyclic ring system is essentially planar (maximum deviation = 0.032 (2) Å). The dihedral angle between the fluorobenzene ring and the phenanthrene tetracyclic system is 60.83 (4)° and to that of the benzene ring of methoxybenzene is 80.55 (5)°. The dihedral angle between the methoxybenzene and the fluorobenzene rings is 69.45 (6)°. The maximum deviation of C8 atom from the mean plane of the methoxy benzene is -0.021° and that of C7 atom from that of fluorobenzene is 0.059 Å.
In the crystal packing, the molecules are linked by C-H···O intermolecular interactions into infinite chains running paralell to the b axis. The crystal structure is further stabilized by C-H···Cg interactions (Table 1), where Cg1 is the centre of gravity of N1/C7/N2/C15/C16, Cg2 is the center of gravity of C1-C6 and Cg3 is the center of gravity of C15/C16/C17/C22/C23/C28.
Yield: 0.84 g(50%). The compound was dissolved in dimethyl sulfoxide and allowed to evaporate slowly, until single crystals were grown.

Refinement
The hydrogen atoms were placed in calculated positions with C-H = 0.93 Å to 0.96 Å, refined in the riding model with fixed isotropic displacement parameters: U iso (H) = 1.5U eq (C)for methyl group and U iso (H) = 1.2U eq (C)for other groups.

Figure 2
A unit cell packing diagram for the title compound. Intermolecular hydrogen bonds are shown as dashed lines.