1-[(Biphenyl-4-yl)(phenyl)methyl]-1H-imidazole (bifonazole)

In the title compound, C22H18N2, the dihedral angles formed by the imidazole ring with the phenyl ring and the benzene ring of the biphenyl group are 87.02 (5) and 78.20 (4)°, respectively. In the crystal, molecules interact through intermolecular C—H⋯N hydrogen bonds, forming chains parallel to the b axis. These chains are further linked into a three-dimensional network by C—H⋯π stacking interactions

In the title compound, C 22 H 18 N 2 , the dihedral angles formed by the imidazole ring with the phenyl ring and the benzene ring of the biphenyl group are 87.02 (5) and 78.20 (4) , respectively. In the crystal, molecules interact through intermolecular C-HÁ Á ÁN hydrogen bonds, forming chains parallel to the b axis. These chains are further linked into a threedimensional network by C-HÁ Á Á stacking interactions

Related literature
For a review of the antimicrobial activity of bifonazole and its therapeutic use in superficial mycoses, see: Lackner and Clissold (1989 Table 1 Hydrogen-bond geometry (Å , ).

Comment
Bifonazole is a broad-spectrum antifungal agent, mainly used by topical application in the treatment of fungal skin infections, including nail infections (Lackner & Clissold, 1989). In the crystal structure of the racemate, layers of the R and S enantiomer alternate along the c axis. Figure 1 shows the S configuration of the chiral center at atom C7. The dihedral angles between the different rings are 26.17 (8)° for the two aromatic rings of the biphenyl group, 101.80 (4)° for the imidazole ring and the benzene ring of the biphenyl group, 62.34 (5)° for the phenyl ring and the benzene ring of the biphenyl group, and 92.98 (5)°f or the imidazole ring and the phenyl ring. In the crystal structure, molecules are linked by intermolecular C-H···N hydrogen bonds (Table 1) into chains running parallel to the b axis. The chains are further connected by C-H···π stacking interactions to form a three-dimensional network.

Experimental
A saturated solution of the title compound was prepared by adding an excess of powder to 20 ml of diethyl ether. Subsequent to stirring the suspension overnight, filtration was performed using a 0.2 µm PTFE syringe filter (13 mm, VWR International, LLC, West Chester, PA, USA). The solution was transferred into a 20 ml scintillation vial in 20 ml scintillation vials (Research Products International Corp., Mt. Prospect, IL, USA) and three holes were pierced in the cap of the vial to allow the solvent to slowly evaporate. After one week, all solvent had evaporated and crystals of the title compound were obtained.

Refinement
H atoms were placed in calculated positions and treated as riding on their parent atoms with C-H = 0.95 Å (aromatic), 1.00 Å (aliphatic) and with U iso (H) = 1.2 U eq (C). Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. H atoms are presented as small spheres of arbitrary radius.  Refinement. Outlier data were removed using a local program based on the method of Prince and Nicholson.

1-[(Biphenyl-4-yl)(phenyl)methyl]-1H-imidazole
Refinement on F 2 for ALL reflections except for 0 with very negative F 2 or flagged by the user for potential systematic errors.