In the initial dimer conformation, prior to structural optimization, benzene and imidazole occupy the same position relative to a given binding site, specifically at 3.55±0.05 Å parallel to the site. A similar distance was used in the generation procedure of S66x8 dataset . Here, the aromatic ring of the small monomer was aligned with that of the binding site, ensuring that the distance between the corresponding pair of heavy atoms on the two rings remained within a margin of 0.05 Å. Each dimer was then optimized using non-empirical hybrid density functional theory (DFT) with many-body dispersion approach (range-separated self-consistent screening, MBD@rsSCS), namely PBE0+MBD, in conjunction with tightly-converged numeric atom-centered orbitals ("tight settings"), as implemented in the FHI-aims 72 software. We classify the resulting structures into three categories based on their shape: 'Linear', where the original chain-like geometry is mainly preserved; 'Semi-Folded', where parts of the large monomer bend while other sections remain linear; and 'Folded', where the large monomer encases the smaller ones. Following this classification, the first letter of the dimer names corresponds to the structural category: 'F' for Folded, 'SF' for Semi-Folded, and 'L' for Linear. The small monomer is indicated by the letter 'B' for benzene or 'I' for imidazole, while the number that follows indicates the binding site (in QUID dimers as found viable post-optimization). The chemical diversity of the equilibrium QUID dimers (represented by the counts of non-H elements) is plotted in Fig. of the SI against the radius of gyration, illustrating the spread of the three structural categories. Furthermore, we acknowledge that modeling ligand-pocket systems would be incomplete without computing nonequilibrium dimer conformations, which are crucial for understanding the binding of drugs to protein pockets. To this end, we generated eight optimized out-of-equilibrium structures along the reaction pathway of the non-covalent bond for 16 representative molecular dimers (F2B1, F2I1, F2B2, F2I2, SF2B1, SF2I1, SF2B2, SF2I2, SF2B3, SF2I3, L2B1, L2I1, L2B2, L2I2, L2B3, L2I3). These non-equilibrium conformations were constructed with inter-monomer distances ranging from 3.2Å to 7.1Å, defined by a dimensionless multiplicative factor q, which represents the ratio of the inter-monomer distance in a given conformation to that in its equilibrium state. The chosen values of q are 0.90, 0.95, 1.00, 1.05, 1.10, 1.25, 1.50, 1.75, and 2.00, as shown in Fig. . For the π-π interactions between aromatic rings, the dissociation vector was defined as the distance between the plane of the aromatic ring on the large monomer and the center of mass of the small monomer. In the case of H-bonds, dissociation was measured between the proton acceptor and donor atoms. All the non-equilibrium geometries were also optimized at PBE0+MBD level with "tight" settings using FHI-Aims (version 221103). Unlike the equilibrium dimers, the heavy atoms of the binding site and small monomer were kept frozen in their respective positions during optimization. An example of the dissociation geometries for one of the non-equilibrium dimers is shown in Fig. .