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Volume 68 
Part 5 
Pages o1423-o1424  
May 2012  

Received 20 March 2012
Accepted 11 April 2012
Online 18 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.127
Data-to-parameter ratio = 16.4
Details
Open access

9,10-Dioxoanthracene-1,4-diyl bis(4-methylbenzenesulfonate)

aResearch Centre for Bioorganic Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand,bProgram of Bachelor of Science in Applied Chemistry (BSAC), Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand,cComputational Chemistry Unit Cell, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand, and dCenter of Petroleum, Petrochemicals and Advanced Materials, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand
Correspondence e-mail: nongnuj.j@chula.ac.th

The title molecule, C28H20O8S2, has a T-shaped conformation. The central 9,10-anthraquinone moiety is bow-shaped with the two outer aromatic rings being inclined to one another by 13.99 (11)°. The benzenesulfonate rings are inclined to one another by 47.35 (12)°, and by 34.51 (11) and 17.88 (11)° to the bridging aromatic ring of the 9,10-anthraquinone moiety. In the crystal, C-H...O interactions link the molecules into ribbons in [100].

Related literature

For background to the structures of anthraquinones and their biological activity, see: Zielske (1987[Zielske, A. G. (1987). J. Org. Chem. 52, 1305-1309.]); Yatsenko et al. (2000[Yatsenko, A. V., Chernyshev, V. V., Popov, S. I., Sonneveld, E. J. & Schenk, H. (2000). Dyes Pigm. 45, 169-176.]); Huang et al. (2004[Huang, S. H., Chiu, H. F., Lee, A. L., Guo, C. L. & Yuan, C. L. (2004). Bioorg. Med. Chem. 12, 6163-6170.]); Meng et al. (2005[Meng, Q., Zhang, W., Yu, J. & Huang, D. (2005). Dyes Pigm. 65, 281-283.]); García-Sosa et al. (2006[García-Sosa, K., Villarreal-Alvarez, N., Lübben, P. & Peña-Rodríguez, L. M. (2006). J. Mex. Chem. Soc. 50, 76-78.]); Cho et al. (2006[Cho, E. J., Yeo, H. M., Ryu, B. J., Jeong, H. A. & Nam, K. C. (2006). Bull. Korean Chem. Soc. 27, 1967-1968.]); Carland et al. (2010[Carland, M., Grannas, M. J., Cairns, M. J., Roknic, V. J., Denny, W. A., McFadyen, W. D. & Murray, V. (2010). J. Inorg. Biochem. 104, 815-819.]). For related structures, see: Swaminathan & Nigam (1967[Swaminathan, S. & Nigam, G. D. (1967). Curr. Sci. 36, 541.]); Cao et al. (2007[Cao, L.-P., Wang, Y.-Z., Gao, M. & Zhou, B.-H. (2007). Acta Cryst. E63, o1876-o1877.]).

[Scheme 1]

Experimental

Crystal data
  • C28H20O8S2

  • Mr = 548.56

  • Triclinic, [P \overline 1]

  • a = 9.6796 (2) Å

  • b = 10.9426 (3) Å

  • c = 13.1833 (4) Å

  • [alpha] = 111.122 (1)°

  • [beta] = 90.961 (1)°

  • [gamma] = 107.190 (1)°

  • V = 1232.41 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 296 K

  • 0.35 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker, (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.912, Tmax = 0.948

  • 12983 measured reflections

  • 5616 independent reflections

  • 3997 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.127

  • S = 1.02

  • 5616 reflections

  • 343 parameters

  • 346 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O4i 0.93 2.48 3.333 (3) 153
C3-H3...O8ii 0.93 2.49 3.245 (3) 139
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker, (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker, (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5268 ).


Acknowledgements

We thank the Organizing Commitee for a bursary to attend the XXII IUCr 2011 Congress, the American Crystallographic Association (ACA) for a scholarship to attend the 2009 ACA Summer Course in Small Molecule Crystallography, the 90th Anniversary of Chulalongkorn University Fund (Ratchadaphisek Somphot Endowment Fund), the Thai Government Stimulus Package 2 (TKK2555) project, the Center for Petroleum Petrochemicals and Advanced Materials, and the Research Centre for Bioorganic Chemistry (RCBC), Chulalongkorn University, for financial support.

References

Bruker, (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, L.-P., Wang, Y.-Z., Gao, M. & Zhou, B.-H. (2007). Acta Cryst. E63, o1876-o1877.  [CSD] [CrossRef] [details]
Carland, M., Grannas, M. J., Cairns, M. J., Roknic, V. J., Denny, W. A., McFadyen, W. D. & Murray, V. (2010). J. Inorg. Biochem. 104, 815-819.  [ISI] [CrossRef] [ChemPort] [PubMed]
Cho, E. J., Yeo, H. M., Ryu, B. J., Jeong, H. A. & Nam, K. C. (2006). Bull. Korean Chem. Soc. 27, 1967-1968.  [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
García-Sosa, K., Villarreal-Alvarez, N., Lübben, P. & Peña-Rodríguez, L. M. (2006). J. Mex. Chem. Soc. 50, 76-78.
Huang, S. H., Chiu, H. F., Lee, A. L., Guo, C. L. & Yuan, C. L. (2004). Bioorg. Med. Chem. 12, 6163-6170.  [CrossRef] [PubMed] [ChemPort]
Meng, Q., Zhang, W., Yu, J. & Huang, D. (2005). Dyes Pigm. 65, 281-283.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Swaminathan, S. & Nigam, G. D. (1967). Curr. Sci. 36, 541.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yatsenko, A. V., Chernyshev, V. V., Popov, S. I., Sonneveld, E. J. & Schenk, H. (2000). Dyes Pigm. 45, 169-176.  [CSD] [CrossRef] [ChemPort]
Zielske, A. G. (1987). J. Org. Chem. 52, 1305-1309.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o1423-o1424   [ doi:10.1107/S1600536812015814 ]

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