Abstract

The asymmetric unit of the title 1:1 salt 1,2,4-triazolium hydrogen oxalate, C2H4N3 +·C2HO4 - (I), comprises one 1,2,4-triazolium cation and one hydrogen oxalate anion. In the crystal, the hydrogen oxalate anions are linked by O-H⋯O hydrogen bonds into chains running parallel to [100]. In turn, the anionic chains are linked through the 1,2,4-triazolium cations by charge-assisted +N-H⋯O- hydrogen bonds into sheets aligned parallel to (01). The sheets are further stacked through π-π inter-actions between the 1,2,4-triazolium rings [centroid-to-centroid distance = 3.642 (3) Å, normal distance = 3.225 (3) Å, slippage 1.691 Å], resulting in the formation of a three-dimensional supra-molecular network. Hirshfeld surface analysis of the title salt suggests that the most significant contributions to the crystal packing are by H⋯O/O⋯H and H⋯N/N⋯H contacts involving the hydrogen bonds.

Highlights

  • The oxalate anion (C2O42–), i.e. the complete deprotonation product of oxalic acid (C2H2O4), is a small, rigid, planar species and has been widely used as a ligand in the formation of coordination polymers (Gruselle et al, 2006; Abraham et al, 2014)

  • The anionic chains are linked by charge-assisted +N—HÁ Á ÁOÀ hydrogen bonds involving the 1,2,4-triazolium cations into sheets extending parallel to (011)

  • In order to quantify the nature of the intermolecular interactions present in the crystal structure, Hirshfeld surfaces (McKinnon et al, 2007) and their associated two-dimensional fingerprint plots (Spackman & McKinnon, 2002) were calculated using CrystalExplorer17 (Turner et al, 2017)

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Summary

Chemical context

The oxalate anion (C2O42–), i.e. the complete deprotonation product of oxalic acid (C2H2O4), is a small, rigid, planar species and has been widely used as a ligand in the formation of coordination polymers (Gruselle et al, 2006; Abraham et al, 2014). This ligand possesses four electron-donating O atoms and can display versatile coordination modes upon metal complexation. During our synthetic efforts to develop novel lanthanide coordination polymers with rigid, short, organic ligands including the oxalate anion, the title salt C2H4N3+ÁC2HO4À (I) was obtained unexpectedly from the reaction of terbium(III) chloride hexahydrate, oxalic acid, and 1,2,4-triazole in water at room temperature. The cationic and anionic molecules are coplanar with an r.m.s. deviation of 0.020 A

Supramolecular features
Hirshfeld surface analysis
Full Text
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