The influence of substitution and weak interactions on the crystal structures of a series of 2,6-disubstituted N-arylthioamides

The synthesis and single crystal X-ray diffraction structures of five 2,6-disubstituted N-arylthioamides, viz. 2,6-difluorophenylthioamide (1), 2,6-dichlorophenylthioamide (2), 2,6-dibromophenylthioamide (3), 2,6-dimethylphenylthioamide (4) and 2-chloro-6-methylphenylthioamide (5), are reported. The primary hydrogen-bonding motif consists of 1-D ribbons of molecules connected by N-H center dot center dot center dot S=C hydrogen bonds and weak C-H/S center dot center dot center dot C interactions. All five N-arylthioamide molecules adopt the cis conformation in the solid state, defined as the conformation where the amine proton is on the same side as the sulfur atom. The chains and ribbons of the five compounds feature a variety of weak intermolecular interactions, including C-H center dot center dot center dot S, C-X center dot center dot center dot p and pi center dot center dot center dot pi interactions.