Received 28 August 2013
aDepartment of Materials Science, School of Engineering, The University of Shiga Prefecture, 2500 Hassaka-cho, Hikone, Shiga 522-8533, Japan, and bDepartment of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan
Correspondence e-mail: email@example.com
The asymmetric unit of the title compound, C14H6O4, contains three independent molecules (A, B and C). In molecule C, there are two disordered sets of two carbonyl O atoms [occupancies = 0.643 (11) and 0.357 (11)]. All three molecules are non-planar due to repulsion between two O atoms in peri positions on the anthracene ring, showing a slight difference in deviation of the carbonyl O atoms. The intramolecular distances between the two nearest O atoms are in the range of 2.685 (10)-2.766 (10) Å. In the crystal, molecules are linked by C-HO and - [centroid-centroid distances = 3.615 (2), 3.844 (2) and 3.921 (2) Å] interactions, which lead to the formation of a herringbone-like arrangement.
For the synthesis of the title compound, see: Yoshino et al. (1981). For applications of 1,4,9,10-anthracenetetraone (quinizarindiquinone) derivatives, see: Isikli & Díaz (2012); Adeva et al. (1997); Jin et al. (1998).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2198 ).
This work was supported by a Grant-in-Aid for Scientific Research (C) (No. 23550161) from the JSPS.
Adeva, M., Caballero, E., García, F., Medarde, M., Sahagún, H. & Tomé, F. (1997). Tetrahedron Lett. 38, 6893-6896.
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Isikli, S. & Díaz, R. (2012). J. Power Sources, 206, 53-58.
Jin, G.-Z., Kim, Y., Chung, J.-H., Sok, D.-E. & Ahn, B.-Z. (1998). Arch. Pharm. 331, 380-384.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yoshino, S., Hayakawa, K. & Kanematsu, K. (1981). J. Org. Chem. 46, 3841-3846.