Synthesis and crystal structure of anti-10-butyl-10,11,22,23-tetrahydro-9H,21H-5,8:15,12-bis(metheno)[1,5,11]triazacyclohexadecino[1,16-a:5,6-a′]diindole

Abstract

The title compound, C33H33N3, is a carbazolophane, which is a cyclophane composed of two carbazole fragments. It has a planar chirality but crystallizes as a racemate in the space group P-1. The molecule adopts an anti-configuration, in which two carbazole fragments are partially overlapped. Both carbazole ring systems are slightly bent, with the C atoms at 3-positions showing the largest deviations from the mean planes. The dihedral angle between two carbazole fragments is 5.19 (3)°, allowing an intramolecular slipped π–π interaction [Cg...Cg = 3.2514 (8) Å]. In the crystal, the molecules are linked via intermolecular C—H...N hydrogen bonds and C—H...π interactions into a network sheet parallel to the ab plane. The molecules of different sheets form other C—H...π interactions, thus forming a three-dimensional network.