A molecular rotor built with a stator formed by two rigid 9 beta-mestranol units having a 90 degrees bent angle linked to a central phenylene rotator has an ideal structure to examine aromatic CH/p interactions. Energies and populations of the multiple solution conformations from quantum-mechanical calculations and molecular dynamics simulations were combined with variable-temperature (VT) H-1 NMR data to establish the enthalpy of this interaction and the entropy associated with rotation about a single bond. Rotational dynamics in the solid state were determined via VT cross-polarization magic-angle spinning C-13 NMR spectroscopy.