Crystal structure and Hirshfeld surface analysis of -(2-chloro-phenyl-carbamo-thio-yl)-4-fluoro-benzamide and -(4-bromo-phenyl-carbamo-thio-yl)-4-fluoro-benzamide.

The title compounds, CHClFNOS () and CHBrFNOS (), were synthesized by two-step reactions. The dihedral angles between the aromatic rings are 31.99 (3) and 9.17 (5)° for and , respectively. Compound features an intra-molecular bifurcated N-H⋯(O,Cl) link due to the presence of the -Cl atom on the benzene ring, whereas features an intra-molecular N-H⋯O hydrogen bond. In the crystal of , inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate (8) loops. The extended structure of 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 and H⋯H (19.7%), C⋯H/H⋯C (14.8%) and Br⋯H/H⋯Br (12.4%) contacts for .