The title molecular salt, C5H10N3
+·Cl−, was obtained as by-product in the attempted synthesis of a histamine derivative. The terminal amino group of the starting material is protonated. The Cimidazole—C—C—N(H3)+ group in the cation is in an anti conformation with a torsion angle of 176.22 (10)°. In the crystal, cations and anions are linked via N—H⋯N and N—H—Cl hydrogen bonds, forming a two-dimensional network parallel to (10-1). A single weak C—H⋯Cl hydrogen bond completes a three-dimensional network.
The crystal structure of the title molecular salt, C5H11N3
+·2Cl−, was redetermined. In comparison with the previous study [Bonnet et al. (1975 ▸). Bull. Soc. Fr. Mineral. Crist.
98, 208–213.], the positions of some H atoms were corrected, allowing a more accurate description of the hydrogen-bonding scheme. In addition, the absolute structure was also determined. The maximum differences in terms of bond lengths and angles between the two determinations are 0.022 Å and 1.43°, respectively. The organic cation display a anti conformation of the protonated amine function and the imidazolium ring. The dihedral angle between the imidazolium plane and the plane through the C—C—N side chain is 29.58 (3)°. In the crystal, the organic cations and Cl− anions are stacked alternatively into layers parallel to (100). N—H⋯Cl hydrogen bonds between all H atoms of the ammonium group and both N—H groups of the imidazolium ring and the Cl− acceptor anions lead to the linkage of organic and inorganic layers into a three-dimensional network.
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