N-(4-Bromophenyl)methoxycarbothioamide

Abstract

Abstract:The synthesis, spectroscopic and crystallographic characterisation of the title compound, O-methyl-N-4-bromophenyl thiocarbamate, MeOC(=S)N(H)PhBr-4 (1), are described. Spectroscopy confirmed the formation of the compound and the molecular structure was determined crystallographically. Two independent but chemically similar molecules comprise the asymmetric unit of 1. The C-S and C-N bond lengths confirm the presence of the thioamide tautomer. The thione-S and amide-N-H atoms are syn, enabling the formation of amide-N-H . . . S(thione) hydrogen bonds between the two independent molecules that generates a two-molecule aggregate via an eight-membered { . . . HNCS} 2 synthon. The aggregates are connected into a three-dimensional architecture via weak intermolecular interactions, including Br . . . π(4-bromophenyl), S . . . π(4-bromophenyl), and weak Br . . . S halogen bonding contacts. The overall molecular conformation, thioamide tautomer, and the presence of amide-N-H . . . S(thione) hydrogen bonding in the crystal conform with expectation for this class of compound.