Aside from supramolecular chirality, successfully determining the local interactions based on dimer calculations and using them to inform the coarse-grained model has interesting consequences for using this methodology to predict the packing behaviour of novel POCs. Our results highlight how these simulations can provide insights into disorder within the crystal structure. For example, for some of our simulations we get a mixture of layers of cage orientations, suggesting that these cages form in a statistical distribution on crystallisation instead of a completely ordered structure. Moreover, unlike many traditional techniques such as crystal structure prediction, our methodology inherently takes into account the rotational flexibility of the structures due to the geometry optimisation of the dimers. Although not necessary here, for other molecules where conformational flexibility leads to many low energy conformers, using a similar approach we could do a full conformer search and perform dimer calculations on combinations of each of the low energy conformers to find the lowest energy local interactions. This could help mitigate a long term problem in crystal structure prediction, where an increase in the number of conformers leads to a large increase in the computational expense to ensure thorough exploration of the conformational landscape. The dimer calculations presented here are relatively computationally inexpensive, and increasing the number of types of components in the HPMC simulations in order to include multiple conformers does not increase the computational expense of the simulations. Therefore, the methodology laid out in the paper could provide a computationally inexpensive route to predicting polymorphic behaviour of flexible molecules orders of magnitude faster than current computational techniques.