Shape mimicry as a design tool in crystal engineering

James K. Whitesell, Raymond E. Davis, Man Shing Wong, Ning Leh Chang

Research output: Contribution to journalJournal articlepeer-review

2 Citations (Scopus)


The pseudosymmetric chiral sulphoxide 1 was designed with two segments of nearly identical shape but with significantly different electron- donor/acceptor properties. Based on the known high statistical preference for organics to pack in one of the centrosymmetric space groups, formation of molecular crystals of enantiomerically pure 1 was predicted to occur with pseudocentrosymmetry, with 1 also playing the role of its enantiomer and packing as would the racemate. Such a packing motif would lack true centrosymmetry, resulting in a polar axis for the crystal and net additivity of the vectors from nitrogen to sulphur (the direction of polarizability for the molecules). Enantiomeric sulphoxide 1 does form molecular crystals with false centrosymmetry, mimicking P2,/c, and with a substantial net directionality of polarizability vectors. In contrast, enantiomeric sulphoxides 3 and 4 form molecular crystals where the vectors from nitrogen to sulphur in neighbouring molecules are essentially opposed.

Original languageEnglish
Pages (from-to)B32-B34
Number of pages3
JournalJournal of Physics D: Applied Physics
Issue number8B
Publication statusPublished - 14 Aug 1993

Scopus Subject Areas

  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics
  • Acoustics and Ultrasonics
  • Surfaces, Coatings and Films


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