A review of the experimental literature reveals that many calicene derivatives have been synthesized, most commonly with alkyl, aryl and halide substituents. We evaluated one synthesized derivative which is small enough to be computed at the EOM-CCSD level and found that is has a Hund's rule inversion in the S2 state (4). While bare calicene has not been synthesized, reports of the synthesis of substituted derivatives containing strong electron-withdrawing groups suggests that push-pull compounds such as those reported here may be feasible.