Acta Crystallographica Section B

Structural Science

Volume 64, Part 1 (February 2008)

research papers

Acta Cryst. (2008). B64, 50-56 [ doi:10.1107/S0108768107059629 ]

Statistical survey of hydrogen-bond motifs in crystallographic special symmetry positions, and the influence of chirality of molecules in the crystal on the formation of hydrogen-bond ring motifs

S. Eppel and J. Bernstein

Abstract: A statistical survey was carried out to examine the connection between hydrogen-bond ring motifs (synthons) and crystallographic special symmetry positions. In the first part, the probability of common hydrogen-bond ring motifs to occupy specific crystallographic symmetry positions of inversion centers, rotation axes and mirror planes was examined. In the second part the probability of the occurrence of hydrogen-bond ring motifs was compared between crystals of chiral molecules (which cannot form inversion or mirror symmetry) to crystals of achiral molecules and racemic crystals. The results show that the crystallographic inversion center is a very significant component in the formation of hydrogen-bond ring motifs.

Keywords: synthon; hydrogen bond; inversion and mirror symmetry; crystal engineering; Cambridge Structural Database; enantiomers; rotation.