Abstract

In the cation of the title salt [systematic name: 4-(2H-1,3-benzodioxol-5-ylmeth­yl)piperazin-1-ium 2,4,6-tri­nitro­phen­o­late], C12H17N2O2 +·C6H2N3O7 −, the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N—C—C—C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions inter­act through N—H⋯O hydrogen bonds and a weak C—H⋯O inter­action. Weak C—H⋯O inter­actions are also observed between the anions, forming R 2 2(10) graph-set ring motifs. In addition, a weak centroid–centroid π–π stacking inter­action between the aromatic rings of the cation and the anion, with an inter­centroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1).

Highlights

  • In the cation of the title salt [systematic name: 4-(2H-1,3benzodioxol-5-ylmethyl)piperazin-1-ium 2,4,6-trinitrophenolate], C12H17N2O2+C6H2N3O7, the piperazine ring adopts a slightly disordered chair conformation

  • The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N—C—C—C torsion angle of 40.7 (2)

  • The dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)

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Summary

Crystal data

The dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8). The nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1). The cations and anions interact through N—H O hydrogen bonds and a weak C—H O interaction. H O interactions are observed between the anions, forming R22(10) graph-set ring motifs. A weak centroid–centroid – stacking interaction between the aromatic rings of the cation and the anion, with an intercentroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (101)

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