1. All combinations of C-H bonds from sp 2 hybridized C-atoms and directing groups (heteroatom with lone pair) in the substrate, which are between 2 and 5 bonds apart from each other, are detected with SMART patterns. These patterns are general enough to cover all directing groups that were encountered in the literature sample from Chen et al. 2. Next, we identify all relevant palladacycle complexes for the C-H activation using ortho-directing groups. For each match, a complex with the substrate and Pd is formed, here the Pd atom is bonded to the carbon atom of the reaction site and the hetero atom of the directing group, as shown in Figure . A 2D embedding for the complex is generated with RDKit, here all atoms are within a plane, this embedding is usually used only for depictions. We measure the internal bond angles between bonds of the ring involving Pd, the heteroatom of the directing group, and the carbon atom of the reaction site in the 2D embedding.