Hydrogen-bonded sheets in 2-(2-aminophenyl)-1H-benzimidazol-3-ium dihydrogen phosphate

Abstract

The title salt, C(13)H(12)N(3)(+).H(2)PO(4)(-), contains a nonplanar 2-(2-aminophenyl)-1H-benzimidazol-3-ium cation and two different dihydrogen phosphate anions, both situated on twofold rotation axes in the space group C2. The anions are linked by O-H...O hydrogen bonds into chains of R(2)(2)(8) rings. The anion chains are linked by the cations, via hydrogen-bonding complementarities and electrostatic interactions, giving rise to a sheet structure with alternating rows of organic cations and inorganic anions. Comparison of this structure with that of the pure amine reveals that the two compounds generate characteristically different sheet structures. The anion-anion chain serves as a template for the assembly of the cations, suggesting a possible application in the design of solid-state materials.

Dihydrogen phosphate mediated supramolecular frameworks in 2- and 4-chloroanilinium dihydrogen phosphate salts

“…Orthophosphoric acid (H 3 PO 4 ), an inorganic oxy-acid, forms dihydrogen phosphate salts with organic amines, resulting in organicinorganic hybrid systems with potentially powerful hydrogenbonded D/A moieties. The dihydrogen phosphate anions (H 2 PO 4 À ) form substructures in these compounds, generating anionic networks via O-HÁ Á ÁO hydrogen bonds which act as a template for the assembly of cations (Shylaja et al, 2008). A considerable number of dihydrogen phosphate salts are recorded in the Cambridge Structural Database (CSD, Version 5.28; Allen, 2002).…”

Hantzsch 1,4-dihydropyridine esters and analogs: candidates for generating reproducible one-dimensional packing motifs

“…Identifying molecules or chemical groups that generate reproducible packing motifs is one of the challenging areas in engineering solid-state materials (Desiraju & Steiner, 1999;Desiraju, 2007). Anions with the combined strength of electrostatic and hydrogen-bonding interactions are one such system (Braga & Grepioni, 2007;Shylaja et al, 2008). These motifs then could be employed as building modules for the design of novel solid materials with the desired structure and properties.…”

Crystal structure of bis(2-aminoanilinium) hydrogen phosphate

“…Non-covalent interactions, such as hydrogen bonding and other weak interactions, represent the basic set of tools for the construction of elaborate supramolecular architectures of organic or inorganic-organic compounds. In this respect, the potential of monohydrogen and dihydrogen phosphate anions as useful building blocks has been investigated structurally (Shylaja et al, 2008;Oueslati et al, 2007;Jagan et al, 2015;Trojette et al, 1998;Soumhi & Jouini, 1995). Here we report the structure and the self-assembled supramolecular architecture exhibited through the formation of O-HÁ Á ÁO, N-HÁ Á ÁO and N-HÁ Á ÁN hydrogen bonds in bis(2-aminoanilinium) hydrogen phosphate.…”