Crystal structure of 4-(2-methoxyphenyl)piperazin-1-ium 3,5-dintrosalicylate

Abstract

The title salt [systematic name: 4-(2-methoxyphenyl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate], C11H17N2O+·C7H3N2O7−, exhibits secondary nitrogen atoms (N—H) in the 2-methoxyphenylpiperazine (2MeOPP) cation, which is protonated with a phenolic hydrogen atom of 3,5-dinitrosalicylic acid (DNSA). One of the oxygen atoms of the nitro group in the 3,5-dinitrosalicylate anion is disordered over two orientations with occupancy factors of 0.65 (7) and 0.35 (7) . The 2-methoxyphenylpiperazinium cation and 3,5-dinitrosalicylate anion are linked in the asymmetric unit by a bifurcated N—H...O hydrogen bond, which formed is between the H atom in the protonated piperazinium unit of the cation and the carboxylic acid group in the anion. The piperazine ring adopts a chair conformation. The crystal structure features N—H...O and C—H...O hydrogen bonds interactions, which lead to the formation of a sandwich-like arrangement. Hirshfeld surface analysis was used to determine the relative contributions of various intermolecular interactions, indicating that that H...O/O...H (38. 3%) and H...H (31. 8%) contacts are the major contributors.

Keywords

• crystal structure
• proton transfer salts
• 1-(2-methoxyphenyl)piperazinium cation
• 3,5-dinitrosalicylic acid