Solid-state NMR (ssNMR) and ab initio quantum mechanical calculations are used in order to understand and to better characterize the molecular conformation and properties of [2.2]paracyclophane and 1,8-dioxa[8](2,7)pyrenophane. Both molecules are cyclophanes, consisting of an aromatic ring assembly and a cyclic aliphatic chain connected to both ends of the aromatic portion. The aliphatic chain causes curvature in the six-membered aromatic ring structures. This led us to examine how the ring strain due to curvature affects the chemical shifts. Using X-ray structures of both [2.2]paracyclophane and 1,8-dioxa[8](2,7)pyrenophane as our starting model, we calculate the chemical shielding tensors and compare these data with those collected from the C-13 ssNMR FIREMAT experiment. We define curvature of [2.2]paracyclophane and 1,8-dioxa[8](2,7)pyrenophane using the if-orbital axis vector (POAV) pyramidalization angle (theta(p)).