Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 12 (December 2013)


organic compounds



Acta Cryst. (2013). C69, 1541-1544    [ doi:10.1107/S0108270113030771 ]

Head-to-tail square-shaped cyclic hydrogen bonds leading to dimeric aggregates: 1,8-dibenzoyl-2,7-di­hydroxy­naphthalene and a comparison with its analogous benzoyl­naphthalene

S. Mohri, S. Yoshiwaka, K. Isozaki, N. Yonezawa and A. Okamoto

Abstract: The title compound, C24H16O4, crystallized with two independent mol­ecules in the asymmetric unit. Both carbonyl groups in these mol­ecules form intra­molecular O-H...O=C hydrogen bonds with neighbouring hy­droxy groups, affording six-membered cyclic structures. In the crystal, dimeric aggre­gates arise from two intermolecular O-H...O=C hydrogen bonds between both independent molecules, forming head-to-tail square-shaped cyclic ...O...H...O...H... hydrogen bonds. These dimeric aggregates are connected into layers in the bc plane by inter­molecular (naphthalene)C-H...O=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-H...O=C and [pi]-[pi] inter­actions between the benzoyl groups. These results show that the intramolecular O-H...O=C hydrogen bonds in the title compound control the orientations of the benzoyl groups and thus promote the formation of the cyclic intermolecular O-H...O=C interactions involving the same donor and acceptor groups in pairs of molecules.

CCDC reference: 971138

Formula: C24H16O4

Keywords: crystal structure; cyclic hydrogen bonds; 1,8-dibenzoyl-2,7-di­hydroxy­naphthalene; O-H...O=C hydrogen bonds.


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