4-(Hydroxymethyl)phenol

In the molecule of the title compound, C7H8O2, the phenol O and hydroxymethyl C atoms lie in the ring plane [deviations of −0.015 (3) and and 0.013 (3) Å, respectively]. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link molecules into a network. A weak C—H⋯π interaction is also found.

In the molecule of the title compound, C 7 H 8 O 2 , the phenol O and hydroxymethyl C atoms lie in the ring plane [deviations of À0.015 (3) and and 0.013 (3) Å , respectively]. In the crystal structure, intermolecular O-HÁ Á ÁO hydrogen bonds link molecules into a network. A weak C-HÁ Á Á interaction is also found.

Related literature
For a related structure, see: Tale et al. (2003). For bond-length data, see: Allen et al. (1987).

Comment
The reduction of carboxylic acids to alcohols is a key synthetic transformation in organic chemistry. There are several ways to bring about this transformation. It is conventionally carried out using sodium borohydride as a reducing agent. We report herein the crystal structure of the title compound.
In the crystal structure, intermolecular O-H···O hydrogen bonds (Table 1) link the molecules into a network, in which they may be effective in the stabilization of the structure. There also exists a weak C-H···π interaction (Table 1).

Experimental
The title compound was prepared by reducing corresponding carboxylic acid using sodium borohydride in THF solution according to a literatue method (Tale et al., 2003). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

Refinement
H atoms were positioned geometrically, with O-H = 0.82 Å (for OH) and C-H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms, with U iso (H) = xU eq (C,O), where x = 1.5 for OH H and x = 1.2 for all other H atoms. The absolute structure could not be determined reliably, and 605 Friedel pairs were averaged before the last cycle of refinement. Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance mat- 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.