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

ABSTRACT: 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.

SUBMITTER: Akhter S 

PROVIDER: S-EPMC6659326 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature