Received 19 February 2013
The title compound, C32H32O6, crystallized with two independent molecules in the asymmetric unit. Each molecule has essentially the same feature of non-coplanar aromatic rings whereby the two 4-isopropoxybenzoyl groups are twisted in a perpendicular manner to the naphthalene ring and oriented in the same direction (syn-orientation). The benzene rings of the aroyl groups make dihedral angles of 16.13 (7) and 25.31 (7)° in the two molecules. These benzene rings make dihedral angles of 88.38 (8) and 75.32 (7)° with the naphthalene ring system in one molecule, and 89.71 (7) and 82.11 (7)° in the other. In the crystal, molecules are linked via C-HO hydrogen bonds, forming a three-dimensional network. In one independent molecule, the 2-propyl groups of both isopropoxy groups are disordered over two positions with site occupancies of 0.512 (3) and 0.488 (3).
For the synthesis of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For structures of closely related compounds, see: Hijikata et al. (2010); Sasagawa et al. (2011, 2012a,b, 2013).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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: SU2564 ).
The authors express their gratitude to Atsushi Nagasawa and Toyokazu Muto, Department of Organic and Polymer Materials Chemistry, Graduate School, Tokyo University of Agriculture & Technology, and Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for their technical advice. This work was partially supported by the Shorai Foundation for Science and Technology (Tokyo, Japan).
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridgeational Laboratory, Tennessee, USA.
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.
Okamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283-1284.
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012a). Acta Cryst. E68, o2596.
Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012b). Acta Cryst. E68, o3348.
Sasagawa, K., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.
Sasagawa, K., Sakamoto, R., Kusakabe, T., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o146.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.