(E)-N-[(5-Methyl-2-furyl)methylene]-3-nitroaniline

The asymmetric unit of the title compound, C12H10N2O3, contains two crystallographically independent molecules, in which the furan and benzene rings are oriented at dihedral angles of 46.09 (3) and 39.98 (3)°. In the crystal structure, weak intermolecular C—H⋯N hydrogen bonds link the molecules into chains running nearly parallel to the a axis.

The asymmetric unit of the title compound, C 12 H 10 N 2 O 3 , contains two crystallographically independent molecules, in which the furan and benzene rings are oriented at dihedral angles of 46.09 (3) and 39.98 (3) . In the crystal structure, weak intermolecular C-HÁ Á ÁN hydrogen bonds link the molecules into chains running nearly parallel to the a axis.   Table 1 Hydrogen-bond geometry (Å , ).
Schiff base complexes are of great interests for inorganic and bioinorganic chemists. To the best of our knowledge, in the past two decades, Schiff base complexes derived from furaldehydes have been less reported (Li & Zhang, 2005). Furaldehydes are raw materials used for preparing many medicines and industrial products, and some of furfural derivatives have a strong bactericidal ability and their antibacterial activities are fairly broad (Antal et al., 1991;Basta & EI-Saied, 2003). As an extension of our work on the structural characterizations of Schiff bases of furaldehyde derivatives, we report herein the crystal structure of the title compound.
The asymmetric unit of the title compound contains two crystallographically independent molecules ( In the crystal structure, weak intermolecular C-H···N hydrogen bonds (Table 1) link the molecules into chains nearly parallel to the a-axis (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental
For the preparation of the title compound, 5-methyl-2-furaldehyde (11.0 mg, 0.1 mmol) and 3-nitrobenzenamine (13.8 mg, 0.1 mmol) were dissolved in methanol (10 ml). The mixture was stirred for 1 h at room temperature, and then filtered. After allowing the filtrate to stand in air for 7 d, yellow block-shaped crystals of the title compound were obtained. They were collected, washed with methanol and dried in a vacuum desiccator using anhydrous CaCl 2 (yield; 60%).

Refinement
H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with U iso (H) = xU eq (C), where x = 1.2 for aromatic H and x = 1.5 for methyl H atoms. Friedel pairs were merged. Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.   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 Rfactors(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.