2-(4-Methoxyphenoxy)-3-nitropyridine

In the title molecule, C12H10N2O4, the pyridine and benzene rings are almost orthogonal [dihedral angle = 86.69 (11)°], with the pyridine N atom directed towards the centre of the benzene ring. The –NO2 [O—N—C—C = −26.1 (3)°] and –OMe [C—O—C—C = 166.5 (2)°] substituents are not coplanar with their respective aromatic rings. In the crystal, supramolecular layers in the ab plane are formed via C—H⋯π interactions involving methyl H atoms and the pyridine and benzene rings. Short N—O⋯π contacts (where the π-system is derived from the pyridine ring) occur between layers in the c-axis direction.

In the title molecule, C 12 H 10 N 2 O 4 , the pyridine and benzene rings are almost orthogonal [dihedral angle = 86.69 (11) ], with the pyridine N atom directed towards the centre of the benzene ring. The -NO 2 [O-N-C-C = À26.1 (3) ] and -OMe [C-O-C-C = 166.5 (2) ] substituents are not coplanar with their respective aromatic rings. In the crystal, supramolecular layers in the ab plane are formed via C-HÁ Á Á interactions involving methyl H atoms and the pyridine and benzene rings. Short N-OÁ Á Á contacts (where thesystem is derived from the pyridine ring) occur between layers in the c-axis direction.

Comment
Continued studies into the structural chemistry of N-heterocycle derivatives related to the title compound (Nasir et al., 2010) arise owing to interest in examining their fluorescence properties (Kawai et al. 2001;Abdullah, 2005). It was in this context that the synthesis and characterization of the title compound, (I), was investigated.
In (I), Fig. 1, the pyridine ring is orthogonal to the benzene ring [dihedral angle = 86.69 (11) °] and is orientated so that the pyridine-N atom is directed towards the centre of the benzene ring. Whereas the methoxy group is deviates from co-planarity with the benzene ring to which it is connected [the C12-O4-C9-C8 torsion angle = 166.5 (2) °], the nitro group is even further twisted out of the plane of the pyridine ring [O1-N2-C2-C1 = -26.1 (3) °].
In the crystal packing, C-H..π and N-O···π interactions contribute to the stabilization of the structure. The C-H..π interactions involve methyl-H atoms interacting with the pyridine and benzene rings, and lead to the formation of layers in the ab plane, Fig. 2 and Table 1. The layers stack along the c axis and are connected by N-O···π contacts, where the π system is derived from the pyridine ring, Fig. 3 and Table 1.
Experimental 4-Methoxyphenol (1.19 g, 96 mmol) was mixed with sodium hydroxide (0.384 g, 96 mmol) in several drops of water. The water was then evaporated. The paste was heated with 2-chloro-3-nitropyridine (1.49 g, 96 mmol) at 423-433 K for 5 h. The product was dissolved in water and the solution extracted with chloroform. The chloroform phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped colourless blocks of (I).

Refinement
Carbon-bound H-atoms were placed in calculated positions (C-H 0.93-0.96 Å) and were included in the refinement in the riding model approximation, with U iso (H) set to 1.2-1.5U equiv (C). Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.