2-Chloro-1-(3-fluorobenzyloxy)-4-nitrobenzene

In the title compound, C13H9ClFNO3, the benzene rings are oriented at a dihedral angle of 41.23 (5)°. In the crystal structure, intermolecular C—H⋯O interactions link the molecules in a herring-bone arrangement along the b axis and weak π–π contacts between the benzene rings [centroid–centroid distance = 3.881 (1) Å] may further stabilize the structure.


Crystal data
The title compound is one kind of important pharmaceutical intermediates, which is dual ErbB-1/ErbB-2 tyrosine kinase inhibitior (Petrov et al., 2006). We report herein its crystal structure.
In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. In the crystal structure, intermolecular C-H···O interactions link the molecules in herring-bone arrangement along the b axis and π-π contact between the benzene rings, Cg1-Cg2 i , [symmetry code: (i) x, 1/2 -y, 1/2 + z, where Cg1 and Cg2 are centroids of the rings A (C1-C6) and B (C8-C13), respectively] may further stabilize the structure, with centroid-centroid distance of 3.881 (1) Å.

Experimental
For the preparation of the title compound, in the presence of sodium carbonate (10 g), 2-chloro-4-nitrophenol (1 mmol) and 1-(bromomethyl)-3-fluorobenzene (1 mmol) in acetonitrile (25 ml) were stirred at 313 K for 8 h. Sodium carbonate was filtered off and the filtrate was washed with brine. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product, which was crystallized from ethyl acetate to give the title compound. Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.1 g) in ethyl acetate (10 ml) and evaporating the solvent slowly at room temperature for 3 d.

Refinement
H atoms were positioned geometrically with C-H = 0.93 and 0.97 Å for aromatic and methylene H atoms, respectively, and constrained to ride on their parent atoms, with U iso (H) = 1.2U eq (C). Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.