Crystal structure of 8-78-bis­(4-chloro­benzo­yl)-7H-cyclo­penta­aace­naphthylen-9-ylnaphthalene-1-carb­oxy­lic acid

摘要

The title compound, C40H22Cl2O4, was formed by a Michael–Aldol domino reaction sequence, which coupled acenaphthene­quinone with 4-chloro­aceto­phenone in the presence of KOH in methanol. The dihedral angles between the central cyclo­penta­[a]ace­naphthyl­ene fused-ring system (r.m.s. deviation = 0.066 Å) and the 4-chloro­benzoyl rings are 62.25 (10) and 70.19 (10)°. The dihedral angle between the central ring system and the naphthoic acid grouping is 62.46 (7)°. This twisting of the pendant rings facilitates the formation of an intra­molecular aromatic π–π stacking inter­action between the 4-chloro­benzoyl and naphthoic acid rings, with centroid–centroid distances of 3.4533 (16) and 3.5311 (16) Å, and a C—H⋯π inter­action between one of the H atoms of the central moiety and the 4-chloro­benzoyl ring with an H⋯π distance of 2.57 Å. In the crystal, carb­oxy­lic acid inversion dimers generate R 2 ²(8) loops. The dimers are linked by weak C—H⋯O and C—H⋯Cl hydrogen bonds and C—H⋯π inter­actions, generating a three-dimensional architecture.