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Volume 69 
Part 11 
Page o1597  
November 2013  

Received 28 August 2013
Accepted 24 September 2013
Online 2 October 2013

Key indicators
Single-crystal X-ray study
T = 223 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.070
wR = 0.204
Data-to-parameter ratio = 13.9
Details
Open access

Anthracene-1,4,9,10-tetra­one

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: kitamura.c@mat.usp.ac.jp

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-H...O and [pi]-[pi] [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.

Related literature

For the synthesis of the title compound, see: Yoshino et al. (1981[Yoshino, S., Hayakawa, K. & Kanematsu, K. (1981). J. Org. Chem. 46, 3841-3846.]). For applications of 1,4,9,10-anthracene­tetra­one (quinizarindi­quinone) derivatives, see: Isikli & Díaz (2012[Isikli, S. & Díaz, R. (2012). J. Power Sources, 206, 53-58.]); Adeva et al. (1997[Adeva, M., Caballero, E., García, F., Medarde, M., Sahagún, H. & Tomé, F. (1997). Tetrahedron Lett. 38, 6893-6896.]); Jin et al. (1998[Jin, G.-Z., Kim, Y., Chung, J.-H., Sok, D.-E. & Ahn, B.-Z. (1998). Arch. Pharm. 331, 380-384.]).

[Scheme 1]

Experimental

Crystal data
  • C14H6O4

  • Mr = 238.19

  • Monoclinic, C 2/c

  • a = 39.450 (4) Å

  • b = 5.4465 (5) Å

  • c = 32.787 (3) Å

  • [beta] = 119.185 (9)°

  • V = 6150.4 (11) Å3

  • Z = 24

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 223 K

  • 0.55 × 0.08 × 0.04 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • 27613 measured reflections

  • 7016 independent reflections

  • 3239 reflections with I > 2[sigma](I)

  • Rint = 0.126

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.204

  • S = 0.99

  • 7016 reflections

  • 506 parameters

  • 4 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4C-H4C...O1Ai 0.94 2.45 3.373 (5) 169
C5C-H5C...O2Ai 0.94 2.33 3.112 (5) 140
C11A-H11A...O1Cii 0.94 2.55 3.262 (7) 133
C11C-H11C...O3Biii 0.94 2.52 3.113 (4) 121
C12C-H12C...O3Biii 0.94 2.49 3.095 (5) 122
Symmetry codes: (i) -x, -y-4, -z+1; (ii) [x+{\script{1\over 2}}, -y-{\script{5\over 2}}, z+{\script{1\over 2}}]; (iii) [-x, y+1, -z+{\script{1\over 2}}].

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005[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.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2198 ).


Acknowledgements

This work was supported by a Grant-in-Aid for Scientific Research (C) (No. 23550161) from the JSPS.

References

Adeva, M., Caballero, E., García, F., Medarde, M., Sahagún, H. & Tomé, F. (1997). Tetrahedron Lett. 38, 6893-6896.  [CrossRef] [ChemPort] [Web of Science]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Isikli, S. & Díaz, R. (2012). J. Power Sources, 206, 53-58.  [Web of Science] [CrossRef] [ChemPort]
Jin, G.-Z., Kim, Y., Chung, J.-H., Sok, D.-E. & Ahn, B.-Z. (1998). Arch. Pharm. 331, 380-384.  [CrossRef] [ChemPort]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Yoshino, S., Hayakawa, K. & Kanematsu, K. (1981). J. Org. Chem. 46, 3841-3846.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1597  [ doi:10.1107/S1600536813026342 ]

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