(4-Hydroxy-3,5-dimethylphenyl)(phenyl)methanone

In the molecule of the title compound, C15H14O2, the dihedral angle between the benzene and phenyl rings is 61.27 (8)°. In the crystal, O—H⋯O and weak C—H⋯O hydrogen bonds link the molecules into chains extending along the c-axis direction.


Comment
Benzophenone and its derivatives show various biological activities such as anti-fungal and anti-inflamatory (Naldoni et al., 2009 andSelvi et al., 2003). The presence of various substituents in the benzophenone nucleus is essential in determining the quantitative structure-activity relationships for 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 these compounds exhibit antifungal properties (Naveen et al., 2006) In view of its extensive background, the title compound, C 15 H 14 O 2 , was prepared and characterized by single-crystal X-ray diffraction and the structure is reported herein.
In the molecular structure of this compound (Fig. 1), bond lengths and angles do not show large deviations from and are comparable with those reported for a similar structure (Mahendra et al., 2005). The dihedral angle between the two benzene rings is 61.27 (8)°. The crystal structure is stabilized by intermolecular O-H···O and weak C-H···O hydrogen bonds, forming one-dimensional chains extending along the c axis in the unit cell (Fig. 2).

Experimental
(4-Hydroxy-3,5-dimethyl-phenyl)phenyl-methanone was synthesized by the Fries rearrangement. 2,6-Dimethylphenyl benzoate (0.022 mol) was mixed with anhydrous aluminium chloride (0.044 mol) and fused at 150-170 °C under dry conditions for about 2-3 h. The reaction mixture was then cooled to room temperature and quenched with 6 M HCl in the presence of ice water. The reaction mixture was stirred for about 2-3 h, then filtered and the product was recrystallized from ethanol to obtain colourless crystals.

Refinement
All H-atoms were located from difference maps but were then positioned geometrically and refined using a riding model, with C-H = 0.93-0.96 Å and and O-H = 0.82 Å, with U iso (H) = 1.2U eq (C) (aromatic) or 1.5U eq (C) (methyl or O). One reflection (0 2 0) was considered to be seriously affected by beamstop interference and was omitted from the data set.   Packing diagram of the molecule in the unit cell viewed down the a axis.  (6) 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 esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq O5 0.0022 (