The title compound, C40H22Cl2O4, was formed by a Michael-Aldol domino reaction sequence, which coupled acenaphthenequinone with 4-chloroaceto-phenone 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 22(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.
|Number of pages||4|
|Journal||Acta Crystallographica Section E: Structure Reports Online|
|Publication status||Published - 1 Jan 2015|
Bibliographical noteJPJ and CK are obliged to Dr S. Prathapan for introducing them to the field of domino reactions. SAIF (STIC) CUSAT, Kochi, India, provided spectroscopic, analytical and single crystal X-ray diffraction data.
- Crystal structure
- Domino reaction
- Hydrogen bonding