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.

cmldisplay filedownload file

Chemical Markup Language (CML) file (6.8 kbytes)
[ doi:10.1107/S0108270113030771/fg3312Isup3.cml ]
Supplementary material


To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

 bibliographic record in  format

  Find reference:   Volume   Page   
  Search:     From   to      Advanced search

Copyright © International Union of Crystallography
IUCr Webmaster