Racemic mefloquinium chloro-difluoro-acetate: crystal structure and Hirshfeld surface analysis.

ABSTRACT: In the racemic title mol-ecular salt, C₁₇H₁₇F₆N₂O⁺·C₂ClF₂O₃^- (systematic name: 2-{[2,8-bis-(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium chloro-difluoro-acetate), the cation, which is protonated at the piperidine N atom, has the shape of the letter, L, with the piperidin-1-ium group being approximately orthogonal to the quinolinyl residue [the C_q-C_m-C_m-N_a (q = quinolinyl; m = methine; a = ammonium) torsion angle is 177.79?(18)°]. An intra-molecular, charge-assisted ammonium-N-H?O(hydrox-yl) hydrogen bond ensures the hy-droxy-O and ammonium-N atoms lie to the same side of the mol-ecule [O_h-C_m-C_m-N_a (h = hydrox-yl) = -59.7?(2)°]. In the crystal, charge-assisted hydroxyl-O-H?O^-(carboxyl-ate) and ammonium-N⁺-H?O^-(carboxyl-ate) hydrogen bonds generate a supra-molecular chain along [010]; the chain is consolidated by C-H?O inter-actions. Links between chains to form supra-molecular layers are of the type C-Cl??(quinolinyl-C₆) and the layers thus formed stack along the a-axis direction without directional inter-actions between them. The analysis of the calculated Hirshfeld surface points to the dominance of F?H contacts to the surface (40.8%) with significant contributions from F?F (10.5%) and C?F (7.0%) contacts.

SUBMITTER: Wardell JL 

PROVIDER: S-EPMC6038619 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature