International Union of Crystallography, Acta Crystallographica Section E: Crystallographic Communications, 7(75), p. 1026-1029, 2019
DOI: 10.1107/s2056989019008569
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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.