Crystal structure of 5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxyl-ate: an unexpected salt arising from the deca-rboxylation of both precursors

Acta Crystallogr E Crystallogr Commun. 2015 Jun 24;71(Pt 7):840-3. doi: 10.1107/S205698901501172X. eCollection 2015 Jul 1.

Abstract

Both the 3-amino-2H,4H-1,2,4-triazolium cation and the pyrazine-2-carboxyl-ate anion in the title salt, C2H5N4 (+)·C5H3N2O2 (-), were formed by an unexpected deca-rboxylation reaction, from 5-amino-1H-1,2,4-triazole-3-carb-oxy-lic acid and pyrazine-2,3-di-carb-oxy-lic acid, respectively. The dihedral angle between the pyrazine ring (r.m.s. deviation = 0.008 Å) and the carboxyl-ate group in the anion is 3.7 (3)°. The extended structure of the salt contains a supra-molecular zigzag tape in which cations and anions are engaged in strong and highly directional N-H⋯N,O hydrogen bonds, forming R 2 (2)(8) and R 2 (2)(9) graph-set motifs. The packing between the tapes is mediated by π-π stacking inter-actions between the triazole and pyrazine rings.

Keywords: crystal structure; deca­rboxylation; hydrogen bonding; ionothermal synthesis; triazolium salt; π–π stacking inter­actions.