1-(3,3-Dichloroallyloxy)-4-methyl-2-nitrobenzene

In the title compound, C10H9Cl2NO3, the dihedral angle between the benzene ring and the plane of the nitro group is 39.1 (1)°, while that between the benzene ring and the plane through the three C and two Cl atoms of the dichloroallyloxy unit is 40.1 (1)°. In the crystal, C—H⋯O hydrogen bonds to the nitro groups form chains along the b axis. These chains are linked by inversion-related pairs of Cl⋯O interactions at a distance of 3.060 (3) Å, forming sheets approximately parallel to [-201] and generating R 2 2(18) rings. π–π contacts between benzene rings in adjacent sheets, with centroid–centroid distances of 3.671 (2) Å, stack molecules along c.

In the title compound, C 10 H 9 Cl 2 NO 3 , the dihedral angle between the benzene ring and the plane of the nitro group is 39.1 (1) , while that between the benzene ring and the plane through the three C and two Cl atoms of the dichloroallyloxy unit is 40.1 (1) . In the crystal, C-HÁ Á ÁO hydrogen bonds to the nitro groups form chains along the b axis. These chains are linked by inversion-related pairs of ClÁ Á ÁO interactions at a distance of 3.060 (3) Å , forming sheets approximately parallel to [201] and generating R 2 2 (18) rings.contacts between benzene rings in adjacent sheets, with centroid-centroid distances of 3.671 (2) Å , stack molecules along c.
This study was supported financially by the Capital University of Economics and Business (00891162721716)

Dong-mei Ren Comment
The title compound is an important intermediate in the synthesis of phenanthrenes, which can be utilized to synthesize organic semiconductors and conjugated polymers (Walker et al., 2005). These materials are of wide current interest with applications in electronic and optoelectronic devices including light-emitting diodes (Kolosov et al., 2002). We report here the crystal structure of the title compound, (I), as we have interests in this field.

Experimental
The title compound, (I) was prepared by a method reported in literature (Walker et al., 2005). The crystals were obtained by dissolving (I) (0.1 g) in methanol (30 ml) and evaporating the solvent slowly at room temperature for about 8 d.

Refinement
All H atoms were positioned geometrically and constrained to ride on their parent atoms, with C-H = 0.93 Å for aromatic H and 0.96 Å for alkyl H, respectively. The U iso (H) = xU eq (C), where x = 1.2 for aromatic H and x = 1.5 for other H.

Figure 2
A packing diagram of (I). 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq