Syntheses, crystal structures and Hirshfeld surface analysis of three salts of 1-(4-nitro­phenyl)­piperazine

Archana, S. D. and Foro, Sabine and Yathirajan, H. S. and Kiran Kumar, H. and Balerao, Rishik and Butcher, Ray J. (2023) Syntheses, crystal structures and Hirshfeld surface analysis of three salts of 1-(4-nitro­phenyl)­piperazine. Acta Crystallographica Section E, 79 (4). pp. 373-379. ISSN 2056-9890

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Abstract

The structures and Hirshfeld surface analysis of three salts of 1-(4-nitro­phenyl)­piperazine are discussed. In 4-(4-nitro­phen­yl)piperazin-1-ium salicylate (C10H14N3O2+·C7H5O3−), there are strong hydrogen bonds between cation and anion and the 4-nitro­phenyl substituent occupies an equatorial position in the piperazinium ring. The cation and anion are linked together by supra­molecular inter­actions [graph-set notation of hydrogen bonding [C_{2}^{2}](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 inter­action between a hydrogen atom on the piperazine ring and the phenyl ring within the salicyclate anion. In bis­[4-(4-nitro­phen­yl)piperazin-1-ium] bis­(4-fluoro­benzoate) trihydrate (2C10H14N3O2+·2C7H4FO2−·3H2O), there are two cations, two anions, and three water mol­ecules of solvation in the asymmetric unit, all linked by hydrogen bonds [graph-set notation of hydrogen bonding R22(20) between adjacent cations and R33(9) between a cation and its adjacent anion]. In the anion, the 4-nitro­phenyl 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 inter­action. Additionally, there is a C—H⋯π inter­action between a hydrogen atom on the phenyl ring within a cation and the phenyl ring within an anion. In 4-(4-nitro­phen­yl)piperazin-1-ium 3,5-di­nitro­benzoate (C10H14N3O2+·C7H4N2O6−), there is a strong N—H⋯O hydrogen bond linking the cation and anion and the 4-nitro­phenyl 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 R22(8), R44(12) and R44(20) rings propogating in the a-axis direction. The nitro­phenyl group is disordered with occupancies of 0.806 (10) and 0.194 (10).

Item Type:	Article
Uncontrolled Keywords:	crystal structure, piperazinium salt, Hirshfeld surface analysis, salicylate, graph-set notation, axial and equatorial substitution patterns in piperazinium rings
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	C Swapna Library Assistant
Date Deposited:	01 Apr 2023 06:14
Last Modified:	01 Apr 2023 06:14
URI:	http://eprints.uni-mysore.ac.in/id/eprint/17467

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