In the present study we will apply this methodology to explore a more complex reaction system, involving a ternary halogen-bonded cocrystal composed of 1,3,5-trifluoro-2,4,6-triodobenzene (tftib) acting as a halogen bond donor, combined with two halogen bond acceptors: pyrazine (pyr) and triphenylphosphine sulphide (tpss) (Fig. ). In addition to the ternary cocrystal, the abovementioned molecules also form two binary cocrystals, namely (tftib)(tpss) and (tftib)(pyr)1/2. Furthermore, the (tftib)(tpss) cocrystal exists in two polymorphic forms (CSD refcodes RUWVEN and RUWPUX), however all our mechanochemical reactions resulted in the formation of only one polymorph, RUWVEN (See ESI Fig. ), therefore throughout this manuscript, we will be referring to this specific polymorph as (tftib)(tpss). We will explore the thermodynamic stability of the ternary cocrystal with respect to the individual coformers and binary cocrystals, by using a combination of periodic DFT calculations and dissolution calorimetry measurements. We will then investigate the role of individual supramolecular interactions found in binary and ternary cocrystal structures in order to provide insights on how these interactions contribute to the overall cocrystal stability.