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Volume 69 
Part 5 
Page o788  
May 2013  

Received 12 March 2013
Accepted 18 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.152
Data-to-parameter ratio = 11.9
Details
Open access

9,10-Dioxo-9,10-dihydroanthracene-1,4-diyl diacetate

aInstitute of Molecular Science, Chemical Biology and Molecular Engineering Laboratory of Education Ministry, University of Shanxi, Taiyuan, Shanxi 030006, People's Republic of China, and bResearch Institute of Applied Chemistry, University of Shanxi, Taiyuan, Shanxi 030006, People's Republic of China
Correspondence e-mail: yincx@sxu.edu.cn

In the title compound, C18H12O6, the anthraquinone ring system is nearly planar [maximum deviation = 0.161 (3) Å] and both acetate groups are located on the same side of the ring plane. A supramolecular architecture arises in the crystal owing to [pi]-[pi] stacking between parallel benzene rings of adjacent molecules [centroid-centroid distance = 3.883 (4) Å] and weak intermolecular C-H...O hydrogen bonding.

Related literature

For applications of the title compound, see: Mal et al. (2007[Mal, D., Ray, S. & Sharma, I. J. (2007). J. Org. Chem. 72, 4981-4984.]). For related compounds, see: Gianneschi et al. (2005[Gianneschi, N. C., Masar, M. S. & Mirkin, C. A. (2005). Acc. Chem. Res. 38, 825-837.]); Thomas (2007[Thomas, J. A. (2007). Chem. Soc. Rev. 36, 856-868.]); Lee & Lin (2008[Lee, S. J. & Lin, W. (2008). Acc. Chem. Res. 41, 521-537.]); Han et al. (2009[Han, Y.-F., Jia, W.-G., Yu, W.-B. & Jin, G.-X. (2009). Chem. Soc. Rev. 38, 3419-3434.], 2010[Han, Y.-F., Li, H. & Jin, G.-X. (2010). Chem. Commun. 46, 6879-6890.]); Lusby (2012[Lusby, P. J. (2012). Inorg. Chem. 108, 292-314.]).

[Scheme 1]

Experimental

Crystal data
  • C18H12O6

  • Mr = 324.28

  • Triclinic, [P \overline 1]

  • a = 8.208 (7) Å

  • b = 9.730 (8) Å

  • c = 9.902 (8) Å

  • [alpha] = 73.257 (16)°

  • [beta] = 79.986 (14)°

  • [gamma] = 80.770 (14)°

  • V = 740.7 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.20 × 0.15 × 0.12 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.987

  • 4006 measured reflections

  • 2610 independent reflections

  • 1616 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.152

  • S = 1.01

  • 2610 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18A...O2i 0.96 2.51 3.425 (4) 159
Symmetry code: (i) -x+3, -y+1, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5688 ).


Acknowledgements

The authors gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China (grant Nos. 21072119, 21102086), Shanxi Provincial Natural Science Foundation (grant No. 2012021009-4), Shanxi Province Foundation for Returnee (grant No. 2012-007), the Taiyuan Technology star special (grant No. 12024703) and CAS Key Laboratory of Analytical Chemistry for Living Biosystems Open Foundation (grant No. ACL201304).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gianneschi, N. C., Masar, M. S. & Mirkin, C. A. (2005). Acc. Chem. Res. 38, 825-837.  [CrossRef] [PubMed] [ChemPort]
Han, Y.-F., Jia, W.-G., Yu, W.-B. & Jin, G.-X. (2009). Chem. Soc. Rev. 38, 3419-3434.  [CrossRef] [ChemPort] [PubMed]
Han, Y.-F., Li, H. & Jin, G.-X. (2010). Chem. Commun. 46, 6879-6890.  [CrossRef] [ChemPort]
Lee, S. J. & Lin, W. (2008). Acc. Chem. Res. 41, 521-537.  [CrossRef] [PubMed] [ChemPort]
Lusby, P. J. (2012). Inorg. Chem. 108, 292-314.  [ChemPort]
Mal, D., Ray, S. & Sharma, I. J. (2007). J. Org. Chem. 72, 4981-4984.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Thomas, J. A. (2007). Chem. Soc. Rev. 36, 856-868.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o788  [ doi:10.1107/S1600536813010635 ]

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