Abstract
The title compound, C40H22Cl2O4, was formed by a Michael-Aldol domino reaction sequence, which coupled acenaphthene-quinone with 4-chloro-aceto-phenone in the presence of KOH in methanol. The dihedral angles between the central cyclo-penta-[a]ace-naphthyl-ene fused-ring system (r.m.s. deviation = 0.066 Å) and the 4-chloro-benzoyl 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 intra-molecular aromatic π-π stacking inter-action between the 4-chloro-benzoyl and naphthoic acid rings, with centroid-centroid distances of 3.4533 (16) and 3.5311 (16) Å, and a C-H⋯π inter-action between one of the H atoms of the central moiety and the 4-chloro-benzoyl ring with an H⋯π distance of 2.57 Å. In the crystal, carb-oxy-lic 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 inter-actions, generating a three-dimensional architecture.
Highlights
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
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 – stacking interaction between the 4-chlorobenzoyl and naphthoic acid rings, with centroid–centroid distances of 3.4533 (16) and
Summary
Domino reactions (Sousa et al, 2014; Kumar & Perumal 2014; Pokhodylo et al, 2014; Feng et al 2014; Ramachandran et al., 2014; Basetti et al, 2014), called cascade or tandem reactions, are usually carried out to enable the efficient construction of complex molecules from simple substrates with high atom economy. 4-chloroacetophenone (2) in the presence of methanolic KOH (Fig. 1)
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