The crystallization of racemic eightphenone 2a from CH2Cl2/MeOH afforded a single crystal suitable for X-ray diffraction analysis, which revealed that 2a exhibits a figure-eight structure identical to that reported by Cameron and Chan (Figure ). The strain energy of 2a has been estimated to be 15.5 kcal mol -1 , based on a hypothetical homodesmotic reaction using density functional theory (DFT) calculations at the B3LYP/6-31G(d) level (Figure ).