Crystal structure prediction was performed using a quasi-random sampling procedure, as implemented in our in-house Global Lattice Energy Explorer (GLEE) software (version 2). Molecules were generated via a conformation search in Maestro using the OPLS2005 forcefield (no cutoff and a dielectric of 1.0) using a mixed torsional/low-mode search with a maximum of 10000 steps allowed. Conformers with an energy less than 35 kJ mol -1 above the lowest energy structure and with an RMSD of greater than 0.3 Å were retained. Each unique conformer was re-optimized using density functional theory (DFT) at the B3LYP GD3BJ/6-311G** level of theory using Gaussian09. Redundant conformers with an RMSD < 0.3 Å were eliminated. These molecular geometries were then held rigid throughout crystal structure generation and lattice energy minimization. Initial crystal generation involves a low-discrepancy sampling of all structural variables within each space group: unit cell lengths, angles, molecular positions and orientations within the asymmetric unit. Space-group symmetry was then applied, and a geometric test was performed for overlap between molecules. Molecular clashes were removed by lattice expansion. Lattice energy calculations were performed with using DMACRYS2.2.1.0 with atom-atom repulsion and dispersion interactions modelled with the FIT intermolecular potential, in conjunction with a spline. Electrostatic interactions were modelled using an atomic multipole description of the molecular charge distribution (up to hexadecapole on all atoms) from the B3LYP/6-311G**-calculated charge density using a distributed multipole analysis (version 2). Charge-charge, charge-dipole and dipole-dipole interactions were calculated using Ewald summation; all other intermolecular interactions were summed to a cut-off between molecular centres-of-mass (15 Å for pyrene, 20 Å for TPhP and 25 Å for all others). For each structure multiple rigid lattice energy minimizations were performed.