Three new fluorinated N-phenyl-substituted pentacyclic ethanoanthracenedicarboximides.

Diels-Alder reaction between maleimides featuring 3,5-di-, 2,4,6-tri- and pentafluorinated N-phenyl substituents and anthracene yields the corresponding pentacyclic ethanoanthracenedicarboximide compounds, namely N-(3,5-difluorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide, C(24)H(15)F(2)NO(2), (IIa), N-(2,4,6-trifluorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide, C(24)H(14)F(3)NO(2), (IIb), N-(2,3,4,5,6-pentafluorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide, C(24)H(12)F(5)NO(2), (IIc). The crystal structures of (IIa)-(IIc) reveal an expected molecular geometry with a `V'-shape of the anthracene-derived tricyclic moiety. The crystal packings of (IIa) and (IIb) are dominated by π-π and C-H···O/F interactions, while F···F and C-H···π contacts are absent. In contrast, (IIc) shows F···F and C-H···O/F contacts, but no π-involved contacts of relevance.