Syntheses, crystal structures and Hirshfeld surface analysis of 4-(4-nitrophenyl)piperazin-1-ium trifluoroacetate and 4-(4-nitrophenyl)piperazin-1-ium trichloroacetate

Abstract

The synthesis and crystal structures of the molecular salts of 4-(4-nitrophenyl)piperazine with trifluoroacetate, namely, 4-(4-nitrophenyl)piperazin-1-ium trifluoroacetate, C10H14N3O2+·C2F3O2− (I), and with trichloroacetate, namely, 4-(4-nitrophenyl)piperazin-1-ium trichloroacetate, C10H14N3O2+·C2Cl3O2−, (II), are reported and compared. A partial positional disorder of the anions was found. In both structures, the piperazine rings adopt a chair conformation, whereas the positions of the nitrophenyl group on the piperazine ring differ from bisectional in (I) to equatorial in (II). In both structures, the supramolecular assemblies are mono-periodic on the basis of the chain-of-rings motifs supported by aromatic π–π interactions. Hirshfeld surface analysis was used to explore the intermolecular close contacts in both crystals. The most dominant contacts of the Hirshfeld surface of the cation–anion pairs of the asymmetric units are O...H/H...O, and those with a contribution of halogen atoms: F...H/H...F in (I) and Cl...H/H...Cl in (II), respectively.

Keywords

• crystal structure
• piperazine
• hydrogen bonding
• chain of rings
• supramolecular assembly