3-[3-(2-Fluorobenzoyl)thioureido]propionic acid

In the title compound, C10H11FN3O3S, the 2-fluorobenzoyl and proponic acid groups maintain a trans–cis conformation with respect to the thiono C=S bond across their C—N bonds. The propionic acid group adopts an anti conformation about the C—C bond, with an N—C—C—C torsion angle of 173.8 (2)°. The amino groups are involved in the formation of intramolecular N—H⋯O and N—H⋯F hydrogen bonds. In the crystal, pairs of O—H⋯O hydrogen bonds link molecules into inversion dimers.

In the title compound, C 10 H 11 FN 3 O 3 S, the 2-fluorobenzoyl and proponic acid groups maintain a trans-cis conformation with respect to the thiono C S bond across their C-N bonds. The propionic acid group adopts an anti conformation about the C-C bond, with an N-C-C-C torsion angle of 173.8 (2) . The amino groups are involved in the formation of intramolecular N-HÁ Á ÁO and N-HÁ Á ÁF hydrogen bonds. In the crystal, pairs of O-HÁ Á ÁO hydrogen bonds link molecules into inversion dimers.

Comment
In continuation of our study of thiourea derivatives containing propionic acid fragments (Yusof et al., 2003;Ngah et al., 2006), we report here the crystal structure of the title compound (I).

Experimental
30 ml acetone solution of β-alanine (2.92 g, 32.80 mmol) was added into a round-bottom flask containing a solution of 2fluorobenzoylchloride (5.21 g, 32.80 mmol) and ammonium thiocyanate (2.50 g, 32.80 mmol). The solution mixture was refluxed for 5 h then filtered off into a beaker containing some ice and left to evaporate at room temperature. The yellowish precipitate obtained was washed with water and cold ethanol. The yellowish crytals were obtained by recrystallization of the precipitate in acetonitrile, suitable for X-ray analysis.

Refinement
The hydroxyl H-atom [O3-H3A] was located from Fourrier map and refined isotropically. Other H atoms were  The molecular structure of (I), with displacement ellipsods drawn at the 50% probability level. Dashed lines denote intramolecular hydrogen bonds.

Figure 2
A portion of the molecular packing of (I) viewed down the c axis. Dashed lines denote intermolecular O-H···O hydrogen bonds. 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.