Crystal Structure Generation and Optimisation. CSP was performed using the Global Lattice Energy Explorer (GLEE) package, which uses quasi-random sampling of crystal packing variables to generate trial crystal structures uniformly distributed across the lattice energy landscape, followed by rigid-molecule lattice energy minimisation using an anisotropic atom-atom intermolecular force field. All resulting local energy minima are treated as possible crystal structures of the molecule. Space group symmetry is used to reduce the dimensionality of the search space, so that only the position and orientation of molecules in the asymmetric unit are sampled, with all other molecules in the unit cell generated by symmetry. In this study, we restrict ourselves to generating crystal structures with one independent molecule in the asymmetric unit (Z = 1). We sampled the 26 most commonly observed space groups for organic molecular crystals (listed in Supporting Information); these space groups cover over 99.4% of Z ≤ 1 structures in the CSD. These space groups were sampled equally, irrespective of their observed frequency in the CSD: quasi-random structures are generated and lattice energy minimised until 10,000 successfully energy minimised crystal structures were found in each space group (260,000 structures per molecule). The CSP process is highly parallelisable, as each crystal structure structure is independent. Trial crystal that passed geometric checks were lattice energy-minimised in three stages. Non-electrostatic interactions (principally intermolecular dispersion and exchangerepulsion) were described by the FIT exp -6 force field , supplemented by fluorine parameters from Williams and Houpt.(59) At the final stage of optimisation, performed using DMACRYS, the FIT potential was applied with atomic multipole electrostatics. Full details are provided in Supporting Information. It is commonplace that multiple unique initial configurations optimise to the same local energy minimum. We remove these duplicates by fast comparison of simulated powder Xray diffraction patterns, followed by structural comparisons using the COMPACK (60) algorithm as implemented in the CSD Python API.