Cocrystallates of fullerene C60 and antiaromatic planar tetraoxaisophlorins have been characterized by single crystal X-ray diffraction analysis. The ring-juncture bonds of C60 are found to be at a very close distance to the plane of the antiaromatic isophlorins. NMR measurements and MALDI-TOF mass spectrometry show that this interaction can persist in both solution and gaseous states, which can be attributed to van der Waals dispersion forces.