2-[2-(Hydroxymethyl)phenyl]-1-phenylethanol

The title compound, C15H16O2, has a dihedral angle of 19.10 (5)° between the mean planes of the two benzene rings. There is an intramolecular O—H⋯O hydrogen bond and the C—C—C—C torsion angle across the bridge between the two rings is 173.13 (14)°. The molecules form intermolecular O—H⋯O hydrogen-bonded chains extending along the a axis. C—H⋯π contacts are also observed between molecules within the chains.

Experimental 3-Phenylisocoumarin (1 eq.) was dissolved in 10 volumes of methanol, sodium borohydride (4 eq.) was added to it and stirred at 50° C under nitrogen atmosphere for 4 hrs. Then two more equivalents of NaBH 4 was further added and left overnight at 50° C for completion of the reaction. After TLC analysis, solvent methanol was removed, extracted with ethyl acetate.
The ethyl acetate layer was washed with water, dried with anhydrous Na 2 SO 4 , evaporated to yield the title compound, which was further purified by washing with petroleum ether. Single-crystals for the structure analysis were obtained by slow evaporation of the ethanol solution.

Refinement
All H atoms of (I) were located from a difference Fourier map and refined isotropically [C-H = 0.937 (18)

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 > σ(F 2 ) is used only for calculating Rfactors(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.