Hydro-nium bis-(tri-fluoro-methane-sulfon-yl)amide-18-crown-6 (1/1)

Atsushi Kitada; Yusuke Funasako; Kazuhiko Matsumoto; Rika Hagiwara; Makoto Inokuchi; Kazuhiro Fukami; Kuniaki Murase

doi:10.1107/S2414314620001625

Hydro-nium bis-(tri-fluoro-methane-sulfon-yl)amide-18-crown-6 (1/1)

IUCrdata. 2020 Feb 6;5(Pt 2):x200162. doi: 10.1107/S2414314620001625. eCollection 2020 Feb.

Authors

Atsushi Kitada¹, Yusuke Funasako², Kazuhiko Matsumoto³, Rika Hagiwara³, Makoto Inokuchi², Kazuhiro Fukami¹, Kuniaki Murase¹

Affiliations

¹ Department of Materials Science and Engineering, Kyoto University, 36-1, Yoshida-honmachi, Sakyo-ku, Kyoto 606-8501, Japan.
² Department of Applied Chemistry, Faculty of Engineering, Sanyo-Onoda City University, 1-1-1, Daigakudori, Sanyo-Onoda, Yamaguchi, 756-0884, Japan.
³ Department of Fundamental Energy Science, Graduate School of Energy Science, Kyoto University, 36-1, Yoshida-honmachi, Sakyo-ku, Kyoto 606-8501, Japan.

Abstract

The structure of the title compound, H₃O⁺·C₂F₆NO₄S₂ ^-·C₁₂H₂₄O₆ or [H₃O⁺·C₁₂H₂₄O₆][N(SO₂CF₃)₂ ^-], which is an ionic liquid with a melting point of 341-343 K, has been determined at 113 K. The asymmetric unit consists of two crystallographically independent 18-crown-6 mol-ecules, two hydro-nium ions and two bis-(tri-fluoro-methane-sulfon-yl)amide anions; each 18-crown-6 mol-ecule complexes with a hydro-nium ion. In one 18-crown-6 mol-ecule, a part of the ring exhibits conformational disorder over two sets of sites with an occupancy ratio of 0.533 (13):0.467 (13). One hydro-nium ion is complexed with the ordered 18-crown-6 mol-ecule via O-H⋯O hydrogen bonds with H₂OH⋯OC distances of 1.90 (6)-2.19 (7) Å, and the other hydro-nium ion with the disordered crown mol-ecule with distances of 1.85 (6)-2.36 (6) Å. The hydro-nium ions are also linked to the anions via O-H⋯F hydrogen bonds. The crystal studied was found to be a racemic twin with a component ratio of 0.55 (13):0.45 (13).

Keywords: complex cation; crown ether; crystal structure; hydronium; ionic liquid.

Grants and funding

This work was supported financially by Grants-in-Aid for Scientific Research (B) (No. 19H02490: AK) from the Japan Society for the Promotion of Science (JSPS).