Additionally, CH-p interactions are also favorable at longer distances than hydrogen bonding and other electrostatic interactions. Given the range of contributions of individual CH and OH groups to the stabilization of carbohydrate-aromatic CH-p stacking interactions, we aimed to quantify the relationship between orientation and energetic contribution for all defined functional groups (Figure ). We evaluated the orientation of each galactose CH group by computing the distance of the galactose carbon atom (Cn) to the centroid (Ctr) of the nearest aromatic ring (dCn-Ctr), and the angle between the distance vector, dCn-Ctr, and the projection of Cn onto the aromatic ring plane (q Proj-Cn-Ctr), as proposed by Houser and coworkers 51 (Scheme 1). Using the previous maximum distance cutoff of 4.6 Å, we observe that the CH-p interactions in our data set preferentially occupy angles between 5° and 50° (Supporting Information Figure ). The angles and distances are linearly correlated, with shorter distances associated with more acute angles (Supporting Information Figure ).