1-(4-Methoxyphenyl)-2-[4-(trifluoromethyl)phenyl]-1H-phenanthro[9,10-d]imidazole

In the title compound, C29H19F3N2O, a phenanthroline-fused imidazole tetracyclic system, the fused benzene rings deviate slightly from the central ring and make dihedral angles with this ring of 3.47 (8) and 3.05 (8)°. The trifluoromethylphenyl ring is roughly coplanar with the phenanthroline-fused imidazole tetracyclic system [dihedral angle = 11.02 (6)°], while the methoxyphenyl ring is almost perpendicular [dihedral angle = 87.65 (6)°]. There are intramolecular C—H ⋯π interactions involving the methoxyphenyl ring and the central phenanthroline ring, as well as an intermolecular C—H⋯π interaction involving the phenanthroline ring. In addition, there is an intermolecular π–π interaction involving the central phenanthroline ring and the trifluoromethylphenyl ring [centroid–centroid distance = 3.685 (2) Å], as well as C—H⋯N interactions linking the molecules into dimers.

In the title compound, C 29 H 19 F 3 N 2 O, a phenanthroline-fused imidazole tetracyclic system, the fused benzene rings deviate slightly from the central ring and make dihedral angles with this ring of 3.47 (8) and 3.05 (8) . The trifluoromethylphenyl ring is roughly coplanar with the phenanthroline-fused imidazole tetracyclic system [dihedral angle = 11.02 (6) ], while the methoxyphenyl ring is almost perpendicular [dihedral angle = 87.65 (6) ]. There are intramolecular C-H Á Á Á interactions involving the methoxyphenyl ring and the central phenanthroline ring, as well as an intermolecular C-HÁ Á Á interaction involving the phenanthroline ring. In addition, there is an intermolecularinteraction involving the central phenanthroline ring and the trifluoromethylphenyl ring [centroid-centroid distance = 3.685 (2) Å ], as well as C-HÁ Á ÁN interactions linking the molecules into dimers.
In this phenanthroline triclinic ring system, the phenyl rings on either end are slightly deviated from the central ring and make the dihedral angles with this ring of 3.47 (8)° and 3.05 (8)° respectively. The trifluromethyl phenyl ring is almost coplanar with the phenanthroline fused imidazole tetracyclic system (dihedral angle of 11.02 (6)°) while methoxy phenyl ring is almost perpendicular (dihedral angle of 87.65 (6)°).
The maximum deviation of C9 atom from the mean plane of the tetracyclic phenantherene fused imidazole ring is 0.078 (2)° and that of C29 atom from the methoxy phenyl ring is -0.043 (3)°. The C22 atom of the trifluromethyl phenyl ring is deviated by -0.040 (2)°.
There is an intermolecular π-π interaction involving the central ring phenanthroline ring and the trifluoromethyl phenyl ring (Cg···Cg 3.685 Å, 1-x, -y, 2-z). In addition there C-H···N out-of-plane interactions linking the molecules into dimers as shown in Fig. 2.
The reaction was monitored by TLC and purified by column chromatography using petroleum ether:ethyl acetate (9:1) as the eluent.Yield: 0.74 g (51%)

Refinement
All the hydrogen atoms were geometrically fixed and allowed to ride on their parent atoms with C-H= 0.93 -0.97 Å,and U iso (H) = 1.3U eq (C)

Figure 1
The molecular structure and labelling scheme for (I) with displacement ellipsoids for non-H atoms are drawn at the 30% probability level.  shown. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.18 e Å −3 Δρ min = −0.24 e Å −3 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.