Polysulfonylamine, CLI [1]. Starke und schwache Wasserstoffbrücken in den Kristallstrukturen von 8-Hydroxychinolinium- und 8-Aminochinolinium-dimesylamid / Polysulfonylamines, CLI [1]. Strong and Weak Hydrogen Bonding in the Crystal Structures of 8-Hydroxyquinolinium and 8-Aminoquinolinium Dimesylamide

In order to study hydrogen bonding networks and packing arrangements in ionic organic crystals, low-temperature X-ray structures were determined for two chemically related onium salts BH⁺(MeSO₂)₂ND, where BH⁺ is 8-hydroxyquinolinium (1; monoclinic, space group P2₁/ c, Z´ = 1) or 8-aminoquinolinium (2; monoclinic, P2₁/n, Z´ = 1). The packings are governed by strong hydrogen bonds, π-π stacking interactions and weak hydrogen bonding. In both compounds, hydrogen bonds using the NH/OH donors of the cations and O/N acceptors of the anion result in simple chain polymeric structures, which extend parallel to the y axis and are propagated by translation (1) or 2₁ transformation (2). Moreover, an intramolecular N- H···O hydrogen bond is present in the 8-hydroxyquinolinium cation. As a common feature, the anion substructures are pervaded by hexagonal channels parallel to y, each one accommodating either two separate stacks of translation related cations (1) or a unique (merged) stack of inversion related cations (2). The crystal cohesion is reinforced by numerous weak hydrogen bonds of the types C_ar-H···O=S and CH₂-H···O=S, the latter creating in each structure a topologically different double-chain ribbon of anions. All C-H···O contacts taken into consideration have normalized parameters d(H···O) ≤ 268 pm and θ(CDH···O) ≥ 126°.