2-[(2-Chlorophenyl)(hydroxy)methyl]phenol

In the title compound, C13H11ClO2, the dihedral angle between the mean planes of the 2-chlorophenyl and phenol rings is 87.4 (9)°. The methyl hydroxy group lies nearly perpendicular to the plane of its attached benzene ring [O—C—C—C torsion angle = 84.3 (3)°]. The two hydroxy groups lie on the same side of the molecule and are in a slightly twisted gauche conformation [O—C—C—O torsion angle = 77.1 (8)°] to each other. In the crystal, O—H⋯O hydrogen bonds between nearby methylhydroxy groups form dimers in alternating pairs aligned diagonally along the b axis. A view along the c axis reveals a hexameric aggregate mediated by a ring of six O—H⋯O hydrogen bonds generating an R 6 6(12) motif loop.

In the title compound, C 13 H 11 ClO 2 , the dihedral angle between the mean planes of the 2-chlorophenyl and phenol rings is 87.4 (9) . The methyl hydroxy group lies nearly perpendicular to the plane of its attached benzene ring [O-C-C-C torsion angle = 84.3 (3) ]. The two hydroxy groups lie on the same side of the molecule and are in a slightly twisted gauche conformation [O-C-C-O torsion angle = 77.1 (8) ] to each other. In the crystal, O-HÁ Á ÁO hydrogen bonds between nearby methylhydroxy groups form dimers in alternating pairs aligned diagonally along the b axis. A view along the c axis reveals a hexameric aggregate mediated by a ring of six O-HÁ Á ÁO hydrogen bonds generating an R 6 6 (12) motif loop.
GP thanks the UOM for research facilities to complete MSc dissertation work. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer. intermediates for the synthesis of pharmaceuticals (Ohkuma et al., 2000), including drugs such as diphenhydramine, orphenadrine, diphenidol and phenyltoloxamine. The crystal structures and hydrogen bonding in some diphenylmethanols have been reported (Ferguson et al., 1995). The title compound, 2-[(2-chlorophenyl) hydroxymethyl]phenol, (I), is a derivative of diphenylmethanol and it is used in the perfume and pharmaceutical industries (Meguro et al., 1985).
In (I), the dihedral angle between the mean planes of the 2-chlorophenyl and phenol rings is 87.4 (9)° (

Experimental
The title compound was obtained as a gift sample from R. L. Fine Chem, Bengaluru, India. X-ray quality crystals were obtained from benzene solution by slow evaporation. (m.p.: 368-373 K).

Refinement
H2 was located by a difference map and refined isotropically. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom-H lengths of 0.95Å or 1.00 (CH), or 0.84° (OH).
Isotropic displacement parameters for these atoms were set to 1.2 (CH) or 1.5 (OH) times U eq of the parent atom.