(4-Hydroxy-3-methylphenyl)(phenyl)methanone

In the title compound, C14H12O2, the benzene rings make a dihedral angle of 58.84 (12)°. In the crystal, molecules are linked into chains along the b-axis direction by O—H⋯O hydrogen bonds. These chains are further linked by C—H⋯O hydrogen bonds, forming layers parallel to the bc plane.

In the title compound, C 14 H 12 O 2 , the benzene rings make a dihedral angle of 58.84 (12) . In the crystal, molecules are linked into chains along the b-axis direction by O-HÁ Á ÁO hydrogen bonds. These chains are further linked by C-HÁ Á ÁO hydrogen bonds, forming layers parallel to the bc plane. 147 parameters H-atom parameters constrained Á max = 0.14 e Å À3 Á min = À0.15 e Å À3 Table 1 Hydrogen-bond geometry (Å , ).

Comment
Benzophenone and related compounds have a wide variety of biological activities such as anti-fungal and antiinflammatory (Khanum et al., 2004;Selvi et al., 2003). The presence of various substituents in the benzophenone nucleus is essential to determining the quantitative structure-activity relationships of these systems. The competence of benzophenones as chemotherapeutic agents, especially as inhibitors of HIV-1 reverse transcriptase RT, cancer and inflammation, is well established and their chemistry has been studied extensively. In addition, methyl-substituted benzophenones exhibit chemotherapeutical activity against fungi. Some studies were carried out to show that methylsubstituted benzophenones exhibit anti-fungal properties (Naveen et al., 2006). In view of its extensive background, the title compound was prepared and characterized by single-crystal X-ray diffraction.
In the molecular structure of the title compound ( Fig. 1), bond lengths and angles do not show large deviations and are comparable with those reported for a similar structure (Mahendra et al., 2005). The dihedral angle between the two benzene rings (C1-C6) and (C9-C16) is 58.84 (12)°. The crystal structure is stabilized by intermolecular C-H···O and O -H···O hydrogen bonds (Table 1 & Fig. 2).

Experimental
The title compound was synthesized by Fries rearrangement. 3-Methylphenylbenzoate was treated with anhydrous aluminium chloride (0.002 mol) as a catalyst at 150-170 °C under without solvent condition for about 2-3 h. Then the reaction mixture was cooled to room temperature and quenched with 6 N HCl in the presence of ice water. The reaction mixture was stirred for about 2-4 h, and the solid was filtered and recrystallized with acetonitrile to obtain the title compound.

Refinement
All H-atoms were located in a difference map and then were positioned geometrically (C-H = 0.93-0.96 Å and O-H = 0.82 Å). They were refined using a riding model with U iso (H) = 1.2U eq (C) or 1.5U eq (O, C methyl ) .

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.