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

DOI: 10.1107/s2056989019008569

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

Journal article published in 2019 by Sidra Akhter, Muhammad Iqbal Choudhary, Hina Siddiqui ORCID, Sammer Yousuf ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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 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.