1-[Phenyl(pyridin-2-ylamino)methyl]-2-naphthol

The title compound, C22H18N2O, was synthesized from naphthalen-2-ol, benzaldehyde and pyridin-2-amine. In the crystal, molecules are linked into centrosymmetric R 2 2(16) dimers by pairs of O—H⋯N hydrogen bonds. The molecular conformation is stabilized by an N—H⋯O hydrogen bond. The dihedral angle between the naphthylene ring system and the phenyl ring is 72.86 (12)°.

The title compound, C 22 H 18 N 2 O, was synthesized from naphthalen-2-ol, benzaldehyde and pyridin-2-amine. In the crystal, molecules are linked into centrosymmetric R 2 2 (16) dimers by pairs of O-HÁ Á ÁN hydrogen bonds. The molecular conformation is stabilized by an N-HÁ Á ÁO hydrogen bond. The dihedral angle between the naphthylene ring system and the phenyl ring is 72.86 (12) .
The mixture was stirred at 100°C for 12 h and then added ethanol (15 ml), after heated under reflux for 1 h, the precipitate was filtrated out and washed with ethanol for 3 times to give the title compound. Colourless crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution.

Refinement
All H atoms were detected in a difference map, the H-atom bonded to C1 was refined freely, but all other H-atoms were placed in calculated positions and refined using a riding motion approxmation, with C-H = 0.93-0.98 Å, with U iso (H) = 1.2U eq (C); O-H = 0.82 Å, with U iso (H) = 1.5U eq (O); N-H = 0.86 Å, with U iso (H) = 1.2U eq (N).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq O1