Structures of alkyl-substituted Tröger's base derivatives illustrate the importance of Z' for packing in the absence of strong crystal synthons

Acta Crystallographica. Section B, Structural Science
Christophe M L Vande VeldeSergey Sergeyev

Abstract

Crystal structures of Tröger's base (5,11-methano-2,8-dimethyl-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine) analogues with the methyl groups replaced by ethyl, iso-propyl and tert-butyl groups were studied. The incidence of Z' > 1 structures increases to rather conspicuous levels. The reasons behind this trend are expanded upon, and a possible explanation is given in the flexibility of the alkyl substituents and van der Waals stabilization. In combination these effects allow for an additional stabilization of the packing by small changes in the molecular conformations, thus expanding the size of the asymmetric unit.

References

May 31, 2002·Acta Crystallographica. Section B, Structural Science·Frank H Allen
May 31, 2002·Acta Crystallographica. Section B, Structural Science·Ian J BrunoRobin Taylor
Oct 31, 2003·Acta Crystallographica. Section B, Structural Science·Elna PidcockJason C Cole
Mar 18, 2005·Acta Crystallographica. Section B, Structural Science·Xiang HaoCarolyn Pratt Brock
Mar 23, 2006·Acta Crystallographica. Section B, Structural Science·Elna Pidcock
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
May 23, 2009·Acta Crystallographica. Section B, Structural Science·Trixie Wagner, Andreas Schönleber

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Citations

Feb 27, 2018·Journal of Chemical Theory and Computation·Farren CurtisNoa Marom

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