Strong asymmetric hydrogen bonding in 2-(oxamoylamino)ethylammonium oxamate-oxamic acid (1/1)

Acta Crystallogr C. 2010 Mar;66(Pt 3):o147-50. doi: 10.1107/S0108270110004233. Epub 2010 Feb 24.

Abstract

The title compound, C(4)H(10)N(3)O(2)(+) x C(2)H(2)NO(3)(-) x C(2)H(3)NO(3), contains at least 11 distinct hydrogen-bond interactions showing a great variety of bond strengths. The shortest and strongest hydrogen bond [O...O = 2.5004 (12) A] is found between the uncharged oxamic acid molecule and the oxamate monoanion. The grouping formed by such a strong hydrogen bond can thus be considered as a hydrogen bis(oxamate) monoanion. It lacks crystallographic symmetry and the two oxamate groups have different conformations, showing an asymmetric hydrogen-bond interaction. Significantly, the asymmetry allows us to draw a direct comparison of site basicity for the two inequivalent carboxylate O atoms in the planar oxamate anion. The constituent molecular ions of (I) form ribbons, where all amide and carboxylate groups are coplanar. Graph-set analysis of the hydrogen-bonded networks reveals the R(2)(2)(10) and R(2)(2)(9) homodromic nets as important structure-directing motifs, which appear to be a common feature of many oxamate-containing compounds.

MeSH terms

  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Ions / chemistry
  • Molecular Conformation
  • Molecular Structure
  • Oxamic Acid / analogs & derivatives*
  • Oxamic Acid / chemistry*

Substances

  • 2-(oxamoylamino)ethylammonium oxamate-oxamic acid
  • Ions
  • Oxamic Acid