Although these supramolecular interactions produce chirality within the cage, our results showed that a racemic mixture of the propeller orientations form on crystallisation, instead of crystallising into a homochiral crystal structure, which is in agreement with the experimental crystal structure. However, chiral interactions may be able to be designed into cage structures such that we can target a cage which forms an enantiopure crystal instead of racemic. For example, by placing hydrogen bonding groups on the vertices where the hydrogen bonding network results in preferential isomers in the crystal structure. The results from this paper are therefore a first step toward creating design strategies for realising chiral phenomena in cages such as circularly polarized luminescence for spintronics. By varying the molecular shape and the types of chiral interactions abstractly through coarse-grained models, we could help to inform design principles for targeted solid-state phase behaviour.