2-Methyl-3-nitro-N-{(E)-[5-(4-nitrophenyl)furan-2-yl]methylidene}aniline

In the title Schiff-base type compound, C18H13N3O5, the central furan ring makes dihedral angles of 12.80 (7) and 51.43 (4)° with the terminal benzene rings. The dihedral angle between the benzene rings is 45.43 (3)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into layers parallel to (010). In addition, there are π–π stacking interactions within the layer [centroid–centroid distance = 3.584 (1) Å] and between the layers [centroid–centroid distance 3.751 (1) Å].


2-Methyl
In the title compound (Fig 1), the molecule presents an E configuration with the 2-(4-nitrophenyl)furan group opposite to 1-methyl-2-nitrobenzene group about the N2 ═C11 double bond. This N2 ═C11 double bond distance [1.2783 (19) Å] is longer than the N ═C typical bond distance (Allen et al., 1987), probably due to π conjugation along all the molecule.
In the crystal, C-H···O intermolecular interactions are observed (Table 1)

Refinement
All H atoms were positioned geometrically and refined using a riding model with C-H = 0.93-0.96 Å and U iso (H) = 1.2 or 1.5 U eq (C). A rotating-group model was applied for the methyl groups.  View of the molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level for non-hydrogen atoms. The intramolecular interaction is shown as a dashed line.

Figure 2
The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

2-Methyl-3-nitro-N-{(E)-[5-(4-nitrophenyl)furan-2-yl]methylidene}aniline
Crystal data 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.