(E)-N′-(4-Methoxybenzylidene)-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide

In the title compound, C14H15N5O4, the central –C=N—N—C(=O)—C– bridge is nearly planar [maximum deviation = 0.037 (1) Å] and forms dihedral angles of 7.37 (9) and 73.33 (5)°, respectively, with the benzene and imidazole rings. The dihedral angle between the benzene and imidazole rings is 66.08 (9)°. The methoxy and nitro groups are nearly coplanar with the benzene and imidazole rings, respectively, with a C—O—C—C torsion angle of 5.9 (2)° and an O—N—C—C angle of −0.2 (2)°. In the crystal, molecules are linked by a pair of N—H⋯O hydrogen bonds with an R 2 2(8) ring motif, forming an inversion dimer. The dimers are further interconnected by C—H⋯O hydrogen bonds into a sheet parallel to the (111) plane. A C—H⋯π interaction is also observed between the sheets.

In the title compound, C 14 H 15 N 5 O 4 , the central -C N-N-C( O)-C-bridge is nearly planar [maximum deviation = 0.037 (1) Å ] and forms dihedral angles of 7.37 (9) and 73.33 (5) , respectively, with the benzene and imidazole rings. The dihedral angle between the benzene and imidazole rings is 66.08 (9) . The methoxy and nitro groups are nearly coplanar with the benzene and imidazole rings, respectively, with a C-O-C-C torsion angle of 5.9 (2) and an O-N-C-C angle of À0.2 (2) . In the crystal, molecules are linked by a pair of N-HÁ Á ÁO hydrogen bonds with an R 2 2 (8) ring motif, forming an inversion dimer. The dimers are further interconnected by C-HÁ Á ÁO hydrogen bonds into a sheet parallel to the (111) plane. A C-HÁ Á Á interaction is also observed between the sheets.
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  polymerizing agents, drugs, herbicides and fungicides (Frank & Kalluraya, 2005). Imidazole derivatives show promising antiallergic (Gauthier & Duceppe, 1984), anti-inflammatory, analgesic (Khan & Nandan, 1997) and antibacterial (Khabnadideh et al., 2003) activities. Imidazole derivatives are also useful for the treatment of rheumatoid arthritis and inflammatory diseases (Dobler, 2003). In view of the apparent importance of imidazole derivatives as potential pharmacological agents, and in continuation of our research work in the field of biologically active imidazole derivatives, we report herein the crystal structure of the title compound.

Experimental
The title compound was synthesized by refluxing a mixture of 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide (0.1 mol) and 1-(4-methoxyphenyl)ethanone (0.1 mol) in glacial acetic acid for 1 h. On cooling the reaction mixture to room temperature and evaporation of the solvent under reduced pressure, the solid that separated out was filtered, washed with water and dried. Yellow plate-shaped crystals were grown from ethanol-dioxane mixture by slow evaporation method (m.p. 505 K).

Refinement
The N-bound H atom was located in a difference Fourier map and refined freely [N2-H1N2 = 0.88 (2) Å]. The remaining H atoms were positioned geometrically (C-H = 0.95, 0.98 and 0.99 Å) and refined using a riding model with U iso (H) = 1.2 or 1.5U eq (C). A rotating group model was applied to the methyl group.

Figure 1
The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.  The crystal packing of the title compound viewed along the [101] axis. The dashed lines represent the hydrogen bonds.
For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.  (Cosier & Glazer, 1986) operating at 100.0 (1) K. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.