2-[(4-Chlorophenyl)aminomethyl]phenol

In the title molecule, C13H12ClNO, the two benzene rings are twisted from each other by a dihedral angle of 68.60 (8)°. In the crystal structure, the hydroxy and amino H atoms are involved in intermolecular hydrogen bonds, O—H⋯N and N—H⋯O, respectively, resulting in R 4 4(8) loops about inversion centers.

In the title molecule, C 13 H 12 ClNO, the two benzene rings are twisted from each other by a dihedral angle of 68.60 (8) . In the crystal structure, the hydroxy and amino H atoms are involved in intermolecular hydrogen bonds, O-HÁ Á ÁN and N-HÁ Á ÁO, respectively, resulting in R 4 4 (8) loops about inversion centers.

Related literature
For the properties and structures of related amino compounds, see: Fu et al. (2007Fu et al. ( , 2009 ;. For a description of ring motifs, see: Bernstein et al. (1995).   Table 1 Hydrogen-bond geometry (Å , ).  (Fu et al., 2007;Fu et al., 2009). With the purpose of obtaining phase transition crystals of amino compounds, various amines have been studied and we have developed a series of new organic molecules. In this article, we describe the crystal structure of the title compound.

Crystal data
In the title molecule ( Fig. 1), the two benzene rings are twisted from each other by a dihedral angle of 68.60 (8)°. In the crystal structure, the hydroxyl and amino H atoms are involved in intermolecular hydrogen bonds, O1-H1···N1 and N1-H1A···O1, respectively, resulting in a R 4 4 (8) ring motif (Bernstein et al., 1995) about inversion centers, which plays an important role in stabilizing the crystal structure. The R 4 4 (8) motif units are further linked into a one-dimentional chain along the b axis (Table 1 and Fig. 2).

Experimental
The commercial 2-((4-chlorophenylamino)methyl)phenol (3 mmol) was dissolved in water/EtOH (1:1 v/v) solution. The solvent was slowly evaporated in air affording colourless block-shaped crystals of the title compound suitable for X-ray analysis.

Refinement
The H atoms were fixed geometrically and treated as riding with N-H = 0.89), O-H = 0.82 and C-H = 0.93 and 0.97 Å for aryl and methylene H-atoms, respectively, in riding mode on their parent atoms with U iso (H) = 1.2U eq (C/N/O). Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

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 > 2sigma(F 2 ) is used only for calculating R-factors(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.