Crystal structure and Hirshfeld surface analysis of N-(2-chloro­phenyl­carbamo­thio­yl)-4-fluoro­benzamide and N-(4-bromo­phenyl­carbamo­thio­yl)-4-fluoro­benzamide

摘要

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 intra­molecular bifurcated N—H⋯(O,Cl) link due to the presence of the ortho-Cl atom on the benzene ring, whereas >2 features an intra­molecular 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 inter­action 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.