A fluoresceinophane: 1⁹,4,16-trioxa-1(2,10)-anthracena-2(1,2)-benzenacyclohexadeca­phane-1⁷,3(1⁹H)-dione

A novel macrocycle containing fluorescein, the highly fluorescent title compound, C₃₁H₃₂O₅, has a xanthene core and a benzyl unit that are planar. The latter is rotated by 72.99 (3)° from the xanthene mean plane. The C₁₁ alkyl tether and the xanthene group adopt a cage-like structure and the xanthene adopts a quinoid-type configuration. The compound crystallizes as a racemic mixture with one mol­ecule of each isomer per unit cell. Even though the planes described by the xanthene and the benzene rings of different molecules are separated by 3.341 (4) and 3.73 (1) Å, respectively, there is insufficient overlap between the aryl units to promote [pi]-­stacking.