Ordered Crystals of Fullerenes Produced by Cocrystallization with Halogenated Azatriquinacenes

The growth and structures of three new cocrystals C 9 Cl 6 Br 3 N·C 60, C 9 Cl 6 Br 3 N·C 70, and C 9 Cl 6 H 3 N·3C 70 ·3C 6 H 5 Cl involving fullerenes and halogenated azatriquinacenes are reported. In each case, the fullerene is completely ordered and avoids the orientational disorder found in many crystalline fullerenes and fullerene cocrystals. In each structure, the upper Cl 6 surface of the halogenated azatriquinacene molecule cups a fullerene. In C 9 Cl 6 Br 3 N·C 60 and C 9 Cl 6 Br 3 N·C 70, the molecules are arranged alternately in columns with the lower Br 3 face of the azatriquinacene also interacting with a neighboring fullerene. In C 9 H 3 Cl 6 N·3C 70 ·3C 6 H 5 Cl, one of the fullerenes is cupped by the upper surface of the azatriquinacene, while four chlorobenzene molecules also form a belt around it.