Synthesis and crystal structure of anti-10-(4-cyano­phen­yl)-10,11,22,23-tetra­hydro-9H,21H-5,8:15,12-bis­(metheno)[1,5,11]tri­aza­cyclo­hexadecino[1,16-a:5,6-a′]di­indole di­chloro­methane monosolvate

Abstract

The title compound consists of one anti-4-(1⁹H,5⁹H-3-aza-1,5(3,9)-dicarbazola­cyclo­octa­phane-3-yl)benzo­nitrile (host mol­ecule) and one di­chloro­methane solvate mol­ecule. The host mol­ecule adopts an anti configuration, in which two carbazole rings are partially overlapped, forming an intra­molecular π–π inter­action. In the crystal, the mol­ecules are cross-linked via inter­molecular host–host and host–guest C—H⋯π inter­actions, forming a three-dimensional network.

The asymmetric unit of the title compound is composed of one host mol­ecule, anti-4-(1⁹H,5⁹H-3-aza-1,5(3,9)-dicarbazola­cyclo­octa­phane-3-yl)benzo­nitrile and one di­chloro­methane solvate mol­ecule, C₃₆H₂₈N₄·CH₂Cl₂. The host mol­ecule possesses a planar chirality but crystallizes as a racemate in the space group P2₁/c. It adopts an anti-configuration, in which two carbazole rings are partially overlapped with a parallel orientation. The two carbazole ring systems are slightly bent, and the C atoms at the 3- and 1-positions show the largest deviations from the mean planes. The dihedral angle between two carbazole rings is 9.42 (3)°, forming an intra­molecular parallel π–π inter­action [Cg⋯Cg = 3.2755 (9) Å]. In the crystal, the mol­ecules are linked via host–host and host–guest C—H⋯π inter­actions, forming chain structures along the a-axis direction. The mol­ecules are linked into a ribbon structure along the c-axis direction by further C—H⋯π inter­actions. As a result, The mol­ecules are cross-linked by C—H⋯π inter­actions into a three-dimensional network.