2,3-Dimethyl-1 H-imidazol-3-ium benzene-sulfonate-1,2-dimethyl-1 H-imidazole co-crystal

Noah Cyr; Matthias Zeller; Patrick C Hillesheim; Arsalan Mirjafari

doi:10.1107/S2414314620006896

2,3-Dimethyl-1 H-imidazol-3-ium benzene-sulfonate-1,2-dimethyl-1 H-imidazole co-crystal

IUCrdata. 2020 May 27;5(Pt 5):x200689. doi: 10.1107/S2414314620006896. eCollection 2020 May.

Authors

Noah Cyr¹, Matthias Zeller², Patrick C Hillesheim³, Arsalan Mirjafari¹

Affiliations

¹ Department of Chemistry and Physics, Florida Gulf Coast University, 10501 FGCU Blvd. South, Fort Myers, FL, 33965, USA.
² Purdue University, Department of Chemistry, 560 Oval Drive, West Lafayette, Indiana USA, 47907, USA.
³ Ave Maria University, Department of Chemistry and Physics, 5050 Ave Maria Blvd, Ave Maria FL, 34142, USA.

Abstract

In the title co-crystal, C₅H₉N₂ ⁺·C₆H₅O₃S^-·C₅H₈N₂, the two 1,2-di-methyl-imidazole rings exist as partially protonated moieties in the asymmetric unit as a two-part disordered unit wherein the acidic hydrogen atom is bound to each ring. The two imidazolium cations share a strong hydrogen bond via the acidic hydrogen atom, which is disordered between two positions, being bonded to the first versus second imidazole ring in a 0.33 (2) to 0.67 (2) ratio. A benzene sulfonate anion is present for charge balance and inter-acts with the aromatic H atoms on both imidazole rings as well as with the methyl groups on the rings.

Keywords: crystal structure; imidazolium; ionic crystal; tosylate.

Grants and funding

Funding for this research was provided by: National Science Foundation (grant No. CHE 11625543); American Chemical Society Petroleum Research Fund (grant No. PRF 58975-UR4); Ave Maria University Department of Chemistry and Physics .