A wide variety of common TD-DFT methods predict that chiral cyclophane 1 should exhibit a specific rotation ranging from large ([ α ] D ∼ 1000) to unreasonably large ([ α ] D > 1,000,000) with numerous estimates between these values. Compound 1 was prepared in two steps from 1,8-dichloroanthraquinone, and its X-ray structure showed it to be, as expected, a C 2 -symmetric, roughly triangular macrocycle. Compound 1 was resolved into nearly pure enantiomers by chromatography on a chiral support, and the specific rotations of the two components were determined to be [ α ] D 23 = +1520 and [ α ] D 23 = −1470. These values are large, but not exceptionally so, and the wildly inaccurate TD-DFT estimates of the specific rotation of compound 1 are shown to be closely related to the failure of the same TD-DFT methods to predict accurately the absorption spectrum of 1 .