No / The separation of racemates into pure enantiomers through crystallization is an important industrial process. This study provides further validation of a novel, predictive approach for spontaneous resolution in which crystal structure prediction simulations are used to explore the relative stabilities of racemic solids versus enantiopure solids. 2-(4-Hydroxyphenyl)-2,5,5-trimethylpyrrolidine-1-oxy (compound 1) has previously been shown to be a racemic conglomerate, while a similar compound, 2-(3-hydroxyphenyl)-2,5,5-trimethylpyrrolidine-1-oxy (compound 2), was not. A conformational search using the Dreiding force field revealed 10 conformational minima for compound 1, and 20 for compound 2. Atomic charges were calculated using unrestricted DFT B3LYP 6-311G** optimized structures, and a crystal structure prediction was performed using the Dreiding force field, considering all low-energy gas-phase conformations and all relevant space groups. Analysis of the predicted crystal structures suggests that compound 1 is a racemic conglomerate, but compound 2 is not. This is in agreement with the experimental evidence.