title: 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).
abstract: 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 R2(2)(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.
authors.affiliation: Faculty of Science, Charles University in Prague, Hlavova 2030/8, 128 43 Praha 2, Czech Republic.
authors.forename: Irena
authors.initials: I
authors.lastname: Matulková
authors.affiliation: Faculty of Science, Charles University in Prague, Hlavova 2030/8, 128 43 Praha 2, Czech Republic.
authors.forename: Ivana
authors.initials: I
authors.lastname: Císařová
authors.affiliation: Faculty of Science, Charles University in Prague, Hlavova 2030/8, 128 43 Praha 2, Czech Republic.
authors.forename: Ivan
authors.initials: I
authors.lastname: Němec
authors.affiliation: Institute of Physics, Czech Academy of Sciences, Na Slovance 2, 182 21 Praha 8, Czech Republic.
authors.forename: Jan
authors.initials: J
authors.lastname: Fábry
keywords: aminothiadiazoles; crystal structure; hydrogen bonding; organic acids; oxalate salt; thiadiazole–diacid cocrystals