Three ammonium salts of sulfathiazole: crystallography and anti-microbial assay

Abstract

The crystal and molecular structures of three ammonium salts derived from sulfathiazole are described. In each case, the anion is in the azanide form, features an intramolecular S←O interaction, and adopts a U-shape. The structures of two cations, [R(HOCH 2 CH 2 )NH 2 ] + , namely for R = Me (1) and iPr (2), are unprecedented in the crystallographic literature. Extensive hydrogen bonding is observed in all crystal structures and leads to a two-dimensional array for 1, and three-dimensional architectures for each of 2 and 3 (R = CH 2 CH 2 OH). The salts exhibited anti-microbial activity against a range of Gram-positive and Gram-negative bacteria, and proved bactericidal toward Vibrio parahaemolyticus, but had no advantage over sulfathiazole itself.