The reaction between 5-fluoroisatin and hydroxylamine hydrochloride in acidic ethanol yields the title compound, C₈H₅FN₂O₂, whose molecular structure matches the asymmetric unit and is nearly planar with an r.m.s. deviation for the mean plane through all non-H atoms of 0.0363 Å. In the crystal, the molecules are linked by N—H...N, N—H...O and O—H...O hydrogen-bonding interactions into a two-dimensional network along the (100) plane, forming rings withR₂²(8) andR₁²(5) graph-set motifs. The crystal packing also features weak π–π interactions along the [100] direction [centroid-to-centroid distance 3.9860 (5) Å]. Additionally, the Hirshfeld surface analysis indicates that the major contributions for the crystal structure are the O...H (28.50%) and H...F (16.40%) interactions. Anin silicoevaluation of the title compound with the vascular endothelial growth factor receptor-2 (VEGFR-2) was carried out. The title compound and the selected biological target VEGFR-2 show the N—H...O(GLU94), (CYS96)N—H...O(isatine) and (PHE95)N—H...O(isatine) intermolecular interactions, which suggests a solid theoretical structure–activity relationship.