(Z)-3-[(2-Fluoroanilino)carbonyl]prop-2-enoic acid

In the title molecule, C10H8FNO3, the dihedral angle between the fluorophenyl group and the essentially planar [within 0.064 (3) Å] COC=CCOOH unit, which has a Z configuration, is 19.99 (14)°. There is an intramolecular O—H⋯O bond in the molecule involving the acid –OH group and the adjacent carbonyl O atom. In the crystal, intermolecular N—H⋯O bonds lead to the formation of polymer chains propagating along [011].

In the title molecule, C 10 H 8 FNO 3 , the dihedral angle between the fluorophenyl group and the essentially planar [within 0.064 (3) Å ] COC CCOOH unit, which has a Z configuration, is 19.99 (14) . There is an intramolecular O-HÁ Á ÁO bond in the molecule involving the acid -OH group and the adjacent carbonyl O atom. In the crystal, intermolecular N-HÁ Á ÁO bonds lead to the formation of polymer chains propagating along [011].

Experimental
SA is thankful to Quaid-i-Azam University, Islamabad, Pakistan, for financial support. The Swedish Research Council (VR) is acknowledged for providing funding for the singlecrystal diffractometer. Carboxylic acids are used for therapeutic purposes and for other biological applications as well. Those carboxylic acids which contain N atoms are widely used as antibiotics (Gould et al., 1980). Compounds containing NH and carboxyl groups are of great interest for the synthesis of drugs due to their coordination to biological systems. Compounds containing keto, ester and imide are good anti-HCV agents (Chen et al., 2009). Carboxylic acids are also used as anti-inflammatories (Shen & Walford, 1980) and enzymetic inhibitors (Shen & Walford, 1972). We therefore used maleic anhydride to synthesize the title compound, by condensation with 2-fluoroaniline.

Structure Reports Online
The molecular structure of the title compound is illustrated in Fig. 1. The bond distances and angles are close to those observed in simlar compounds; 3-[(4-bromoanilino)carbonyl]prop-2-enoic acid ) and 3-[(2,4,6-Tricholoroanilino)carbonyl]prop-2-enoic acid . In the molecule there is an intramolecular O-H···O hydrogen bond involving the acid OH group and the adjacent carbonyl O-atom (

Experimental
A solution of maleic anhydride (5 g, 1 mmol) in (300 ml glacial acetic acid) was added to a solution of 2-fluoroaniline (5 ml, 1 mmol) (150 ml glacial acetic acid) in 500 ml beaker at room temperature and the mixture was stirred in fuming hood at room temperature overnight. The light yellow precipitates formed were filtered off, washed with cold distilled H 2 O (200 ml) and air dried. The yellow crystals, suitable for X-ray diffraction analysis, were obtained by recrystallization in acetone:n-hexane (1:1).

Refinement
In the final cycles of refinement, in the absence of significant anomalous scattering effects, 719 Friedel pairs were merged and Δf " set to zero. The OH and NH H-atoms were located from a difference Fourier map and were freely refined: O3-H3B   Table 1 for details).

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles 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 Rfactors(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.