Comparison of the hydrogen-bond patterns in 2-amino-1,3,4-thiadiazolium hydrogen oxalate, 2-amino-1,3,4-thiadiazole–succinic acid (1/2), 2-amino-1,3,4-thiadiazole–glutaric acid (1/1) and 2-amino-1,3,4-thiadiazole–adipic acid (1/1)

摘要

The X-ray single-crystal structure determinations of the chemically related compounds 2-amino-1,3,4-thiadiazolium hydrogen oxalate, C2H4N3S+·C2HO4?, (I), 2-amino-1,3,4-thiadiazole–succinic acid (1/2), C2H3N3S·2C4H6O4, (II), 2-amino-1,3,4-thiadiazole–glutaric acid (1/1), C2H3N3S·C5H8O4, (III), and 2-amino-1,3,4-thiadiazole–adipic acid (1/1), C2H3N3S·C6H10O4, (IV), are reported and their hydrogen-bonding patterns are compared. The hydrogen bonds are of the types N—H...O or O—H...N and are of moderate strength. In some cases, weak C—H...O interactions are also present. Compound (II) differs from the others not only in the molar ratio of base and acid (1:2), but also in its hydrogen-bonding pattern, which is based on chain motifs. In (I), (III) and (IV), the most prominent feature is the presence of an R22(8) graph-set motif formed by N—H...O and O—H...N hydrogen bonds, which are present in all structures except for (I), where only a pair of N—H...O hydrogen bonds is present, in agreement with the greater acidity of oxalic acid. There are nonbonding S...O interactions present in all four structures. The difference electron-density maps show a lack of electron density about the S atom along the S...O vector. In all four structures, the carboxylic acid H atoms are present in a rare configuration with a C—C—O—H torsion angle of ～0°. In the structures of (II)–(IV), the C—C—O—H torsion angle of the second carboxylic acid group has the more common value of ～|180|°. The dicarboxylic acid molecules are situated on crystallographic inversion centres in (II). The Raman and IR spectra of the title compounds are presented and analysed.