During attempts to achieve inter-action between 2-amino-5-ethyl-1,3,4-thia-diazole with oxalyl chloride and 5-mercapto-3-phenyl-1,3,4-thia-diazol-2-thione with various diacid anhydrides, we obtained two co-crystals (organic salts), namely, 2-amino-5-ethyl-1,3,4-thia-diazol-3-ium hemioxalate, C4H8N3S+·0.5C2O4 2-, (I), and 4-(di-methyl-amino)-pyridin-1-ium 4-phenyl-5-sulfanyl-idene-4,5-di-hydro-1,3,4-thia-diazole-2-thiol-ate, C7H11N2 +·C8H5N2S3 -, (II). Both solids were investigated by single-crystal X-ray diffraction and by Hirshfeld surface analysis. An infinite one-dimensional chain along [100] is generated through O-H⋯O inter-actions between the oxalate anion and two 2-amino-5-ethyl-1,3,4-thia-diazol-3-ium cations in compound (I), and a three-dimensional supra-molecular framework is generated through C-H⋯O and π-π inter-actions. In compound (II), an organic salt is formed by a 4-phenyl-5-sulfanyl-idene-4,5-di-hydro-1,3,4-thia-diazole-2-thiol-ate anion and a 4-(di-methyl-amino)-pyridin-1-ium cation, which are combined by an N-H⋯S hydrogen-bonding inter-action, forming a zero-dimensional structural unit. As a result of inter-molecular π-π inter-actions, the structural units are combined into a one-dimensional chain running along the a-axis direction.
Keywords: 1,3,4-thiadiazole derivatives; crystal structure; hydrogen bonding; organic salt.
© Izotova et al. 2023.