The relevance of chirality in space group analysis: A database study of common hydrogen-bonding motifs and their symmetry preferences

Abstract

Datasets of common hydrogen bonding motifs have been generated using the functionality available in the Materials Module of Mercury 2.0. These datasets were divided on the grounds of space group type (centrosymmetric, Sohncke and non-centrosymmetric/non-Sohncke) and chirality. Comparisons of the populations of the subsets revealed interesting correlations between motif symmetry and space group population. Carboxylic acid and cis-amide dimers prefer centrosymmetric space groups irrespective of the chirality of the molecule. Structures containing an amide chain motif or a hydroxy–hydroxy interaction were found in the Sohncke space groups more often than expected, even when the molecule was achiral.