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Crystal structures of six 4-(4-nitro-phenyl)-piperazin-1-ium salts.

ABSTRACT: Six piperazinium salts, namely 4-(4-nitro-phenyl)-piperazin-1-ium 4-bromo-ben-zo-ate dihydrate, C₁₀H₁₄N₃O₂ ⁺·C₇H₄BrO₂ ^-·2H₂O, (I), 4-(4-nitro-phenyl)-pi-per-a-zin-1-ium 4-iodo-benzoate dihydrate, C₁₀H₁₄N₃O₂ ⁺·C₇H₄IO₂ ^-·2H₂O, (II), 4-(4-nitro-phenyl)-piperazin-1-ium 4-hy-droxy-benzoate monohydrate, C₁₀H₁₄N₃O₂ ⁺·C₇H₅O₃ ^-·H₂O, (III), 4-(4-nitro-phenyl)-piperazin-1-ium 4-methyl-benzoate monohydrate, C₁₀H₁₄N₃O₂ ⁺·C₈H₇O₂ ^-·H₂O, (IV), 4-(4-nitro-phenyl)-piperazin-1-ium 4-meth-oxy-benzoate hemihydrate, 2C₁₀H₁₄N₃O₂ ⁺·2C₈H₇O₃ ^-·H₂O, (V), and 4-(4-nitro-phenyl)-piperazin-1-ium 4-eth-oxy-benzoate, 2C₁₀H₁₄N₃O₂ ⁺·2C₉H₉O₃ ^-, (VI), have been synthesized and their crystal structures solved by single-crystal X-ray diffraction, revealing that all of them crystallize in the triclinic space group P except for (V), which crystallizes in the monoclinic space group P2₁/c and has a disordered nitro group. Compounds (I) and (II) are isostructural. The crystal packing of (I)-(V) is constructed from organic chains formed by a combination of hydrogen bonds of type N-H⋯O and/or O-H⋯O and other weak inter-actions of type C-H⋯O and/or C-H⋯π, forming sheets, whereas (VI) shows a cationic and anionic-based layer structure.

SUBMITTER: Mahesha N

PROVIDER: S-EPMC9069513 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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Crystal structures of six 4-(4-nitro-phenyl)-piperazin-1-ium salts.

Mahesha Ninganayaka N Kiran Kumar Haruvegowda H Yathirajan Hemmige S HS Foro Sabine S Abdelbaky Mohammed S M MSM Garcia-Granda Santiago S

Acta crystallographica. Section E, Crystallographic communications 20220426 Pt 5

Six piperazinium salts, namely 4-(4-nitro-phenyl)-piperazin-1-ium 4-bromo-ben-zo-ate dihydrate, C10H14N3O2 +·C7H4BrO2 -·2H2O, (I), 4-(4-nitro-phenyl)-pi-per-a-zin-1-ium 4-iodo-benzoate dihydrate, C10H14N3O2 +·C7H4IO2 -·2H2O, (II), 4-(4-nitro-phenyl)-piperazin-1-ium 4-hy-droxy-ben ...[more]

PMID: 35547797

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Project description:The structures and Hirshfeld surface analysis of three salts of 1-(4-nitro-phenyl)-piperazine are discussed. In 4-(4-nitro-phen-yl)piperazin-1-ium salicylate (C10H14N3O2 +·C7H5O3 -), there are strong hydrogen bonds between cation and anion and the 4-nitro-phenyl substituent occupies an equatorial position in the piperazinium ring. The cation and anion are linked together by supra-molecular inter-actions [graph-set notation of hydrogen bonding (6) propagating in the a-axis direction]. Additionally, there is π-π stacking involving the salicylate anion and the piperazinium cation in adjacent asymmetric units as well as a C-H⋯π inter-action between a hydrogen atom on the piperazine ring and the phenyl ring within the salicyclate anion. In bis-[4-(4-nitro-phen-yl)piperazin-1-ium] bis-(4-fluoro-benzoate) trihydrate (2C10H14N3O2 +·2C7H4FO2 -·3H2O), there are two cations, two anions, and three water mol-ecules of solvation in the asymmetric unit, all linked by hydrogen bonds [graph-set notation of hydrogen bonding R 2 2(20) between adjacent cations and R 3 3(9) between a cation and its adjacent anion]. In the anion, the 4-nitro-phenyl ring occupies an axial substitution position in the piperazinium ring, which is relatively rare. Within the asymmetric unit, the phenyl groups in the cations show an offset π-π inter-action. Additionally, there is a C-H⋯π inter-action between a hydrogen atom on the phenyl ring within a cation and the phenyl ring within an anion. In 4-(4-nitro-phen-yl)piperazin-1-ium 3,5-di-nitro-benzoate (C10H14N3O2 +·C7H4N2O6 -), there is a strong N-H⋯O hydrogen bond linking the cation and anion and the 4-nitro-phenyl ring occupies an axial substitution position in the piperazinium ring, as seen in the previous structure. In the crystal, the cation and the anion form a complex three-dimensional hydrogen-bonded array involving R 2 2(8), R 4 4(12) and R 4 4(20) rings propogating in the a-axis direction. The nitro-phenyl group is disordered with occupancies of 0.806 (10) and 0.194 (10).

Dataset Information

Crystal structures of six 4-(4-nitro-phenyl)-piperazin-1-ium salts.

Publications

Crystal structures of six 4-(4-nitro-phenyl)-piperazin-1-ium salts.

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