1-{(Z)-[(2,3-Dihydroxypropyl)amino]methylidene}naphthalen-2(1H)-one

In the title molecule, C14H15NO3, the ring system is essentially planar, with an r.m.s. deviation of 0.003 Å. The atoms of the ethane-1,2-diol group were refined as disordered over two sets of sites in a ratio of 0.815 (3):0.185 (3). The molecular conformation is stabilized in part by an intramolecular N—H⋯O hydrogen bond, which forms an S(6) ring. In the crystal, molecules are connected by N—H⋯O and O—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100). The network also features weak C—H⋯O hydrogen bonds. Weak C—H⋯π interactions also observed.

In the title molecule, C 14 H 15 NO 3 , the ring system is essentially planar, with an r.m.s. deviation of 0.003 Å . The atoms of the ethane-1,2-diol group were refined as disordered over two sets of sites in a ratio of 0.815 (3):0.185 (3). The molecular conformation is stabilized in part by an intramolecular N-HÁ Á ÁO hydrogen bond, which forms an S(6) ring. In the crystal, molecules are connected by N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds, forming a two-dimensional network parallel to (100). The network also features weak C-HÁ Á ÁO hydrogen bonds. Weak C-HÁ Á Á interactions also observed.
This work was supported by the Ministry of Higher Education of Egypt under the collaporative PhD program 2012. The EPSRC National Crystallography Service is gratefully acknowledged for the X-ray diffraction measurementss. The authors are thankful to Manchester Metropolitan University, Sohag University and Erciyes Universitry for supporting this study. Azomethine compounds, which were named as Schiff's bases in 1864 are extensively incoporated in many pharmaceutical and food industry applications (Prakash & Adhikari, 2011). Elimination of excess drugs from the bloodstream or body is an essential process to protect against potential toxicity. In most cases the more hydrophilic drugs/pharmacophores are the more they are readily excreted by the kidneys in urine (Lin & Lu, 1997). The existance of conjugated double bonds and more hydroxylic groups in bioactive molecules increases not only their hydrophilicity but also the rate of their membrane absorption. Based on such facts we herein report the crystal structure of a potential bioactive hydrophilic azomethine derivative.
The molecluar structure of the title compound (I) is shown in Fig. 1. The naphthalene ring system (C1-C10) is essentially planar with an r.m.s. deviation of 0.003Å. The bond lengths (Allen et al., 1987) and angles are within normal ranges. In the crystal, molecules are connected by N-H···O and O-H···O hydrogen bonds to form a two-dimensional network parallel to (100). The network is further stabilized by weak C-H···O hydrogen bonds. Weak C-H···π interactions also observed. The O-H groups of the minor component of disorder are not considered in the description of the hydrogen bonding.

Experimental
A mixture of 1 mmol (172 mg) 2-hydroxynaphthalene-1-carbaldehyde and 1 mmol (91 mg) 3-aminopropane-1,2-diol in 40 ml ethanol was refluxed and monitored by TLC till completion after 12 h. On cooling of the reaction mixture at room temperature a quantitaive solid product was deposited, filtered and washed with cold ethanol. The crude product was crystallized from ethanol to afford x-ray quality yellow plates (m.p 505 K) in an excellent yield (90.6%) on a slow evaporation at room temperature for 24 h.

Figure 2
Crystal packing of (I) viewed along the b axis. Only the major component of disorder is shown. The hydrogen atoms not involved in the hydrogen bonds have been omitted for clarity. 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. (