(E)-N′-(3-Ethoxy-4-hydroxybenzylidene)-4-methoxybenzohydrazide

In the molecule of the title benzohydrazide derivative, C17H18N2O4, the dihedral angle between the benzene rings is 6.86 (11)°. The methoxy group of the 4-methoxyphenyl fragment deviates slightly [Cmethyl—O—C—C = 10.0 (4)°] with respect to the benzene ring, whereas the ethoxy group of the 3-ethoxy-4-hydroxyphenyl fragment is is almost coplanar [C—O—C—Cmethyl = 178.5 (2)°]. In the crystal, molecules are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional network parallel to the ab plane. C—H⋯π interactions and C⋯O [2.980 (3) Å] short contacts are also observed.

In the molecule of the title benzohydrazide derivative, C 17 H 18 N 2 O 4 , the dihedral angle between the benzene rings is 6.86 (11) . The methoxy group of the 4-methoxyphenyl fragment deviates slightly [C methyl -O-C-C = 10.0 (4) ] with respect to the benzene ring, whereas the ethoxy group of the 3-ethoxy-4-hydroxyphenyl fragment is is almost coplanar [C-O-C-C methyl = 178.5 (2) ]. In the crystal, molecules are linked by N-HÁ Á ÁO, O-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds into a two-dimensional network parallel to the ab plane. C-HÁ Á Á interactions and CÁ Á ÁO [2.980 (3) Å ] short contacts are also observed.
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009  During the course of our on-going research on benzohydrazide derivatives, which have been reported to possess various biological properties such as antibacterial and antifungal (Loncle et al., 2004), antitubercular (Bedia et al., 2006 and antiproliferative (Raj et al., 2007) activities, the synthesis and crystal structures of benzohydrazide derivatives have been reported Horkaew et al., 2011;Promdet et al., 2011). The title compound was synthesized and tested for its antioxidant and antibacterial activities and found to be inactive. An intramolecular O4-H1O4···O3 hydrogen bond generates a S(5) ring motif (Bernstein et al., 1995). Bond distances are of normal values (Allen et al., 1987) and are comparable with those found in related structures Horkaew et al., 2011;Promdet et al., 2011).
The mixture was refluxed for about 5 h and a white solid appeared. The mixture was then cooled to room temperature and filtered. Colourless needle-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from methanol by slow evaporation of the solvent at room temperature after several days. M. p. to be 1.5U eq (C, N, O) for methyl, hydroxy and amine H atoms and 1.2U eq (C) for the remaining H atoms. A rotating group model was used for the methyl groups. 1879 Friedel pairs were merged. Three outliers (2 1 1, 1 4 0, 3 2 12) were omitted for the final refinement.

Figure 1
The molecular structure of the title compound, showing 45% probability displacement ellipsoids. Hydrogen bond are drawn as dashed line.

Figure 2
The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are drawn as dashed lines. 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.