Ordered Crystals of Fullerenes Produced by Cocrystallization with Halogenated Azatriquinacenes

The growth and structures of three new cocrystalsC9Cl6Br3N·C60, C9Cl6Br3N·C70, and C9Cl6H3N·3C70·3C6H5Cl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 Cl6 surface of the halogenated azatriquinacene molecule cups a fullerene. In C9Cl6Br3N·C60 and C9Cl6Br3N·C70, the molecules are arranged alternately in columns with the lower Br3 face of the azatriquinacene also interacting with a neighboring fullerene. In C9H3Cl6N·3C70·3C6H5Cl, one of the fullerenes is cupped by the upper surface of the azatriquinacene, while four chlorobenzene molecules also form a belt around it.