1-Fluoro-4-[(E)-2-nitrovinyl]benzene

The title compound, C8H6FNO2, is almost planar (r.m.s. deviation for the non-H atoms = 0.019 Å) and the conformation across the C=C bond is trans. The C and H atoms of the side chain are disordered over two sets of sites in a 0.56 (3):0.44 (3) ratio. In the crystal, molecules are linked by C—H⋯O interactions, thus forming C(5) chains propagating in [001].

The title compound, C 8 H 6 FNO 2 , is almost planar (r.m.s. deviation for the non-H atoms = 0.019 Å ) and the conformation across the C C bond is trans. The C and H atoms of the side chain are disordered over two sets of sites in a 0.56 (3):0.44 (3) ratio. In the crystal, molecules are linked by C-HÁ Á ÁO interactions, thus forming C(5) chains propagating in [001].

Introduction
Fluorinated aromatic compounds exhibit different biological activities such as antibacterial, analgesic, anticancer, diuretic, anticonvulsant, insecticidal, antifungal and antiviral (Belestskaya et al., 2000). Further, halogenated aromatic derivatives act as a potent peptide deformylase inhibiter. As part of our studies in this area, the title compound was synthesized and its crystal structure determined.

Experimental
The title compound was synthesized by using the method reported in literature (Heck et al., 1968).

Synthesis and crystallization
1-Bromo-4-fluorobenzene (5.7 mmol), tetrabutylammoniumbromide (11.4 mmol), cesium carbonate (17.1 mmol) and palladium acetate (5.0 mmol) were taken in N,N-dimethylformamide (DMF) (20 mL) and stirred for 30 minutes. To this, nitroethene (8.5 mmol) was added and the reaction mixture was stirred at 353K for 14 h under nitrogen atmosphere. The confirmation of the reaction was confirmed by TLC. The organic layer was filtered and DMF was removed under vacuum. The crude product obtained was purified by column chromatography using petroleum ether and ethyl acetate (7:3) as eluent.
Colourless prisms of the title compound was obtained from slow evaporation of the solvent system: petroleum ether : ethyl acetate (8:2).

Refinement
The H atoms were positioned with idealized geometry using a riding model with C-H = 0.93 Å. The isotropic displacement parameters for all H atoms were set to 1.2 times Ueq(C).

Results and discussion
The title compound, C 8 H 6 FNO 2 , is almost planar (r.m.s. deviation for the non-H atoms = 0.019 Å) and the conformation across the C=C bond is trans. The two carbon atoms of the side chain are disordered over two sets of sites with  Molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level. Only major components of the disordered atoms are shown.

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