4-Fluoro-2-(phenylamino)benzoic acid

There are two crystallographically independent molecules in the asymmetric unit of the title compound, which are linked by pairwise O—H⋯O hydrogen bonds.

The title compound, C 13 H 10 FNO 2 , was obtained by the reaction of 2-bromo-4fluorobenzoic acid with aniline.There are two independent molecules, A and B, in the asymmetric unit, with slight conformational differences: the dihedral angles between the aromatic rings are 55.63 (5) and 52.65 (5) � .Both molecules feature an intramolecular N-H� � �O hydrogen bond.In the crystal, the molecules are linked by pairwise O-H� � �O hydrogen bonds to form A-B acid-acid dimers and weak C-H� � �F interactions further connect the dimers.

Structure description
Non-steroidal anti-inflammatory drugs are among the most commonly utilized medicines globally (Abdu et al., 2020).They exhibit anti-inflammatory, antipyretic, and analgesic properties.They are available as both prescription and over-the-counter medications and are employed to treat fever, acute or chronic pain, and various inflammatory conditions such as osteoarthritis and rheumatoid arthritis (Brennan et al., 2021).Anthranilic acid derivatives represent a crucial subset of non-steroidal anti-inflammatory drugs.

Figure 2
Packing of the molecules in the crystal (for clarity, H atoms not involved in hydrogen bonding are omitted).The C1A molecule is shown in red and the C1B molecule in blue.

Figure 1
The molecular structure of the title compound with displacement ellipsoids 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.

data reports data-2
IUCrData (2024).9, x240197 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.The positions of the H atoms attached to the N and O atoms were obtained from a difference Fourier map, which were then relocated to idealised locations.The C-bound H atoms were positioned geometrically with C-H = 0.95 Å and refined as riding atoms.The constraint U iso (H) = 1.2U eq (C,N) or 1.5U eq (O) was applied in all cases.

Table 2
Experimental details.