2-[(E)-Phenyl(2-phenylhydrazin-1-ylidene)methyl]phenol

In the title hydrazone derivative, C19H16N2O, a twist is found between the hydroxyphenyl and N-bound phenyl rings [dihedral angle = 24.37 (7)°]. The C-bound phenyl ring is almost perpendicular to each of these planes [dihedral angles = 75.30 (7) and 86.00 (7)°, respectively]. The conformation about the imine bond [1.2935 (17) Å] is E. The hydroxy group forms an intramolecular hydrogen bond with the imine N atom. Zigzag chains along [001] mediated by N—H⋯O hydrogen bonds feature in the crystal packing.

In the title hydrazone derivative, C 19 H 16 N 2 O, a twist is found between the hydroxyphenyl and N-bound phenyl rings [dihedral angle = 24.37 (7) ]. The C-bound phenyl ring is almost perpendicular to each of these planes [dihedral angles = 75.30 (7) and 86.00 (7) , respectively]. The conformation about the imine bond [1.2935 (17) Å ] is E. The hydroxy group forms an intramolecular hydrogen bond with the imine N atom. Zigzag chains along [001] mediated by N-HÁ Á ÁO hydrogen bonds feature in the crystal packing.
In (I), Fig. 1, the hydroxy-benzene and N-bound phenyl rings are twisted, forming a dihedral angle of 24.37 (7)°. These planes form dihedral angles of 75.30 (7) and 86.00 (7)°, respectively, with the C-bound phenyl ring indicating an almost perpendicular relationship. The hydroxy group forms an intramolecular hydrogen bond with the imine-N1 atom, Table 1.
The most prominent feature of the crystal packing is the formation of zigzag chains along [001] generated by glide symmetry and mediated by N-H···O hydrogen bonds, Fig. 2 and Table 1. Chains pack in the crystal structure with no specific intermolecular interactions between them, Fig. 3.

Refinement
The C-bound H atoms were geometrically placed (C-H = 0.95 Å) and refined as riding with U iso (H) = 1.2U eq (C). The Oand N-bound H atoms were located from a difference map and refined with the distance restraints O-H = 0.84±0.01 and N-H = 0.88±0.01 Å, and with U iso (H) = zU eq (carrier atom); z = 1.5 for O and z = 1.2 for N.

Computing details
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).  The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.   Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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.