Issue 14, 2022

Control of supramolecular chirality in co-crystals of achiral molecules via stacking interactions and hydrogen bonding

Abstract

An approach is proposed to obtain non-centrosymmetric crystal structures using co-crystallization of specific achiral molecules. The co-formers, donors and acceptors of electron density are selected in such a way that they can form two types of supramolecular synthons: infinite H-bonded chains along a 2-fold screw axis and π-stacks propagating by translation. Geometry analysis shows that combination of these synthons in a co-crystal with a 1 : 1 molar ratio of the co-formers leads to a preference for the crystallization in two Sohncke space groups, P21 and P212121, or, probably, in a polar Pna21 space group. Experimental data confirming this suggestion was obtained for co-crystals of 1H-3,5-dinitropyridine-2-one with five polyaromatic hyrdocarbons with different numbers of aromatic rings connected in a different manner. From seven crystal structures, three with a 1 : 1 composition crystallize in Sohncke groups, while four structures with different stoichiometries, including two polymorphs with anthracene, crystallize in the P21/c (or equivalent P21/n) group. The influence of molecular size and crystal composition on the geometry of supramolecular synthons and total crystal packing is discussed. The suggested approach allows constructing crystal structures not only with a specific packing pattern and symmetry, but, to some extent, with a predefined unit cell.

Graphical abstract: Control of supramolecular chirality in co-crystals of achiral molecules via stacking interactions and hydrogen bonding

Supplementary files

Article information

Article type
Paper
Submitted
17 Jan 2022
Accepted
23 Feb 2022
First published
24 Feb 2022

CrystEngComm, 2022,24, 2591-2601

Control of supramolecular chirality in co-crystals of achiral molecules via stacking interactions and hydrogen bonding

I. V. Fedyanin, CrystEngComm, 2022, 24, 2591 DOI: 10.1039/D2CE00081D

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