Received 20 February 2010
In the title compound, C20H16O5, the dihedral angle between the naphthalene ring system and the benzene ring is 67.43 (5)°. The bridging carbonyl C-C(=O)-C plane makes dihedral angles of 82.64 (6) and 41.79 (7)°, respectively, with the naphthalene ring system and the benzene ring. The dihedral angle between the carboxy O-C(=O)-C plane and the benzene ring is 36.38 (7)° and that between the bridging carbonyl C-C(=O)-C plane and the carboxy O-C(=O)-C plane is 51.88 (8)°. The crystal structure is stabilized by intermolecular O-HO and C-HO hydrogen-bonding interactions. An intramolecular C-HO hydrogen bond occurs between a naphthalene H atom and the carbonyl O atom of the carboxy group.
For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009). For related structures, see: Mitsui, Nakaema et al. (2008); Mitsui, Noguchi et al. (2009); Watanabe, Nakaema, Muto et al. (2010); Watanabe, Nakaema, Nishijima et al. (2010); Hijikata et al. (2010).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2323 ).
The authors would express their gratitude to Professor Keiichi Noguchi for his technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Hijikata, D., Nakaema, K., Watanabe, S., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o554.
Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278.
Mitsui, R., Noguchi, K. & Yonezawa, N. (2009). Acta Cryst. E65, o543.
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Watanabe, S., Nakaema, K., Muto, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o403.
Watanabe, S., Nakaema, K., Nishijima, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o615.