Crystal structure of 2-(1H-imidazol-4-yl)ethanaminium chloride

Abstract

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.

Histamine perchlorate

“…The three C3-C4-C5-N3 torsion angles are À64.3 (5), 59.4 (7), and À50 (2) . These values are in contrast to the values reported in the two structures containing histamine cations where these torsion angles are 177.3 (Prout et al, 1974) and 176.22 (10) (Belfilali et al, 2015).…”

“…Histamines are of interest spanning a wide variety of topics, including drug therapeutics (Zlomuzica et al, 2016), cancer (Martinel Lamas et al, 2015), addictions (Nuutinen et al, 2016, and autoimmune (Abiuso et al, 2014) and anxiety disorders (Cacabelos et al, 2016). In view of this interest in histamine, several structures of histamine salts have been determined through X-ray crystallography previously containing both histamine dications (Veidis et al, 1969;Yamane et al, 1973) and histamine cations (Prout et al, 1974;Belfilali et al, 2015).…”

Characterizations of crystalline structure and catalytic activity of zwitterionic imidazole derivatives

“…While the exocyclic angles are obtuse smallest being 117.7(11)° for C 28 -N 32 -H 32 and the largest 131.1(10)° for C 11 -N 12 -H 12 (Fig.1). Our results are in good agreement with those of literature [35].…”