Acta Cryst. (2013). C69, 1541-1544 [ doi:10.1107/S0108270113030771 ]
Abstract: The title compound, C24H16O4, crystallized with two independent molecules in the asymmetric unit. Both carbonyl groups in these molecules form intramolecular O-HO=C hydrogen bonds with neighbouring hydroxy groups, affording six-membered cyclic structures. In the crystal, dimeric aggregates arise from two intermolecular O-HO=C hydrogen bonds between both independent molecules, forming head-to-tail square-shaped cyclic OHOH hydrogen bonds. These dimeric aggregates are connected into layers in the bc plane by intermolecular (naphthalene)C-HO=C interactions. On the other hand, the analogous compound bearing methoxy groups at the 2- and 7-positions of the naphthalene ring, namely 1,8-dibenzoyl-2,7-dimethoxynaphthalene [Nakaema et al. (2008). Acta Cryst. E64, o807], forms a three-dimensional molecular network via C-HO=C and - interactions between the benzoyl groups. These results show that the intramolecular O-HO=C hydrogen bonds in the title compound control the orientations of the benzoyl groups and thus promote the formation of the cyclic intermolecular O-HO=C interactions involving the same donor and acceptor groups in pairs of molecules.
CCDC reference: 971138
Keywords: crystal structure; cyclic hydrogen bonds; 1,8-dibenzoyl-2,7-dihydroxynaphthalene; O-HO=C hydrogen bonds.
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