1-{(Z)-[3-(1-Hydroxyethyl)anilino]methylidene}naphthalen-2(1H)-one

In the title compound, C19H17NO2, the dihedral angle between the benzene ring and the naphthalene ring system is 9.72 (5)°, while the torsion angle of the C—N—C—C bridging group is 179.24 (17)°. The methyl group of the 1-phenylethanol moiety is disordered over two positions with a refined occupancy ratio of 0.775 (5):0.225 (5). The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming zigzag chains propagating along the c-axis direction. Neighbouring chains are linked via C—H⋯O interactions, forming a two-dimensional slab-like network parallel to the bc plane.

In the title compound, C 19 H 17 NO 2 , the dihedral angle between the benzene ring and the naphthalene ring system is 9.72 (5) , while the torsion angle of the C-N-C-C bridging group is 179.24 (17) . The methyl group of the 1-phenylethanol moiety is disordered over two positions with a refined occupancy ratio of 0.775 (5):0.225 (5). The molecular conformation is stabilized by an intramolecular N-HÁ Á ÁO hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by O-HÁ Á ÁO hydrogen bonds, forming zigzag chains propagating along the c-axis direction. Neighbouring chains are linked via C-HÁ Á ÁO interactions, forming a twodimensional slab-like network parallel to the bc plane.

Experimental
Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), PARST (Nardelli, 1995) and PLATON (Spek, 2009  With the increasing incidence of deep mycosis, there has been intense emphasis on the screening of new and more effective antimicrobial drugs with low toxicity. A considerable number of Schiff-base complexes have potential biological interest, being used as more or less successful models of biological compounds (Suslick & Reinert, 1988). Not only have they played a seminal role in the development of modern coordination chemistry (Singh & Adhikari, 2012), but they can also be found at key points in the development of inorganic biochemistry, catalysis and optical materials (Tisato et al., 1994). Further to our on going study on synthesis of versatile bioactive molecules we herein report the synthesis and crystal structure of the title compound.
In the title molecule, Fig.1, the C12-C17 benzene ring and the C1-C10 naphthalene ring system make a dihedral angle of 9.72 (5) °. The torsion angle of the C12-N1-C11-C1 bridging group between these rings is 179.24 (17)°. The bond lengths and angles are within the normal range (Allen et al., 1987). The molecular conformation of is stabilized by an intramolecular N-H···O hydrogen bond generating an S(6) ring motif (Table 1; Bernstein et al., 1995).
In the crystal, molecules are linked by C-H···O and O-H···O hydrogen bonds (Table 1 and Fig. 2), forming zigzag chains running parallel to the ac plane along the c axis direction. These chains are linked via C-H···O interactions forming a two-dimensional slab-like network lying parallel to the bc plane.

Experimental
A mixture of 1 mmol (172 mg) 2-hydroxynaphthalene-1-carbaldehyde and 1 mmol (122 mg) 1-phenylethanol in 50 ml ethanol was refluxed for 5 h at 350 K. The reaction mixture was left to cool down at ambient temperature for 24 h when a solid precipitate was deposited. The reddish crude product was crystallized from ethanol to afford a good yield (195 mg; 67%) of high quality orange plate-like crystals suitable for X-ray diffraction analysis.

Figure 1
The molecular structure of the title molecule, with atom numbering. The displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered methyl group, C19, is shown.   Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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 Occ. (