4,15-Dimethyl-7,12-diazo­niatri­cyclo­[ 2,7 ]hexa­deca-1(12),2,4,6,13,15-hexa­ene dibromide monohydrate

Edward J. Behrman, Alexandar L. Hansen, Chunhua Yuan, Sean Parkin

Research output: Contribution to journalArticlepeer-review


The title compound, C 16 H 20 N 2 2+ ·2Br - ·H 2 O (1) is a member of the class of compounds called viologens. Viologens are quaternary salts of di­pyridyls and are especially useful as redox indicators as a result of their large negative one-electron reduction potentials. Compound 1 consists of a dication composed of a pair of 4-methyl­pyridine rings mutually joined at the 2-position, with a dihedral angle between the pyridine rings of 62.35 (4)°. In addition, the rings are tethered via the pyridine nitro­gen atoms by a tetra­methyl­ene bridge. Charge balance is provided by a pair of bromide anions, which are hydrogen bonded to a single water mol­ecule [D O⋯Br = 3.3670 (15) and 3.3856 (15) Å]. The crystal structure of 1, details of an improved synthesis, and a full analysis of its NMR spectra are presented.

Original languageEnglish
Pages (from-to)1467-1471
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
StatePublished - Sep 1 2020

Bibliographical note

Funding Information:
Funding for this research was provided by: NSF (grant No. CHE1625732 to Sean Parkin).

Funding Information:
The D8 Venture diffractometer was funded by the NSF (MRI CHE1625732), and by the University of Kentucky.

Publisher Copyright:
© 2020 International Union of Crystallography. All rights reserved.


  • atropisomer
  • crystal structure
  • synthesis
  • viologen

ASJC Scopus subject areas

  • Chemistry (all)
  • Materials Science (all)
  • Condensed Matter Physics


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