(18-Crown-6)-bis(tetrahydrofuran)-potassium Anthracenide: The Salt of a Free Radical Anion Crystallizing as a Kryptoracemate

Ivan Bernal, Roger A. Lalancette

Research output: Contribution to journalArticlepeer-review


K[(18-crown-6)-bis(tetrahydrofuran)anthracenide] was independently prepared by three groups, and its structure described by two of them. The third structure description, though listed in the Cambridge Crystallographic Data Centre (CSD) collection, contains no space group or atomic coordinates, but the cell constants leave no doubt that it is the same species as the two others, which were reported in 2006 and 2016. The compound crystallizes in space group P21, with Z′ = 2.0 at T = 123 K and R = 4.91% (I), and at 100 K and R = 4.44% (II); both impressive results in their individual quality and agreement, despite differences in experimental methods and the temperature of data collection. A more detailed examination of the published data for (I) and (II) reveals that the correct description for this very unusual, and thus far unique substance, is that it contains a radical anion crystallizing as a kryptoracemate rather than as a simple example of a Sohncke space group with Z′ = 2.0. The anthracenide anions present in (I) and (II) are virtually identical; in contrast, the internal pair of cationic species differ from one another in the dissymmetry of the flexible tetrahydrofuran ligands, having significantly different internal and external torsional angles. The two THF molecules attached to the K(crown-ether) cations are not centrosymmetrically related, and this is what makes this portion of the asymmetric unit responsible for the crystal being a kryptoracemate. Our presentation will be based on the more fully documented sample (II), unless specifically stated.

Original languageEnglish (US)
Pages (from-to)137-145
Number of pages9
JournalChemistry (Switzerland)
Issue number1
StatePublished - Mar 2022
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Electrochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Chemistry (miscellaneous)


  • asymmetric unit cell (Z′) of crystals
  • crown ether cations
  • crown ethers
  • crystallographic center of mass
  • enantiomorphs
  • free radicals
  • kryptoracemic crystals
  • kryptoracemic pairs
  • molecular dissymmetry
  • molecular overlay diagrams
  • potassium cations
  • radical anions
  • sohncke space groups


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