M Zeller

Document Type


Publication Date


Publication Title

Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials





Publisher Name

International Union of Crystallography


The oxime derivative of [1.1.1]cyclophane cyclotriveratrylene (CTV) was ring expanded utilizing a Beckmann rearrangement to provide a ten-membered N-acetyl macrocyclic amide that crystallizes as a chloroform monosolvate in columnar assemblies manifesting an unusual disorder within the crystal. Columns made up of this structure consist of infinite columnar assemblies of alternating D and L enantiomers and therefore necessarily are made up of a racemate, yet the chiralities of individual molecules in adjacent columns are independent of one another, leading to the overall formation of a two-dimensional solid solution. The random arrangement of the columns within the structure leads to the emergence of a crystallographic mirror plane not reflected by the molecular symmetry, to a change of symmetry from Pna21 to Pnma and to whole-molecule disorder of the bowl-shaped molecules within the columns.


Author Posting © International Union of Crystallography, 2009. This is the author's version of the work. It is posted here by permission of International Union of Crystallography for personal use, not for redistribution. The definitive version was published in Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, Volume B65, 2009.

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