The title compounds, C14H10ClFN2OS (1) and C14H10BrFN2OS (2), were synthesized by two-step reactions. The dihedral angles between the aromatic rings are 31.99 (3) and 9.17 (5)° for 1 and 2, respectively. Compound 1 features an intra-molecular bifurcated N-H⋯(O,Cl) link due to the presence of the ortho-Cl atom on the benzene ring, whereas 2 features an intra-molecular N-H⋯O hydrogen bond. In the crystal of 1, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R 2 2(8) loops. The extended structure of 2 features the same motif but an additional weak C-H⋯S inter-action links the inversion dimers into [100] double columns. Hirshfeld surface analyses indicate that the most important contributors towards the crystal packing are H⋯H (26.6%), S⋯H/H.·S (13.8%) and Cl⋯H/H⋯Cl (9.5%) contacts for 1 and H⋯H (19.7%), C⋯H/H⋯C (14.8%) and Br⋯H/H⋯Br (12.4%) contacts for 2.