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

Teerawatananond, T.; Kerdsamut, C.; Kokpol, S.; Muangsin, N.

doi:10.1107/S1600536812015814

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 (C-C) = 0.003 Å
R = 0.044
wR = 0.127
Data-to-parameter ratio = 16.4
Details

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

Thapong Teerawatananond,^a Chiaranan Kerdsamut,^b Sirirat Kokpol ^c and Nongnuj Muangsin ^d ^*

^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-HO interactions link the molecules into ribbons in [100].

Related literature

For background to the structures of anthraquinones and their biological activity, see: Zielske (1987); Yatsenko et al. (2000); Huang et al. (2004); Meng et al. (2005); García-Sosa et al. (2006); Cho et al. (2006); Carland et al. (2010). For related structures, see: Swaminathan & Nigam (1967); Cao et al. (2007).

Experimental

Crystal data

C₂₈H₂₀O₈S₂
M_r = 548.56
Triclinic, $[P \overline 1]$
a = 9.6796 (2) Å
b = 10.9426 (3) Å
c = 13.1833 (4) Å
= 111.122 (1)°
= 90.961 (1)°
= 107.190 (1)°
V = 1232.41 (6) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.912, T_max = 0.948
12983 measured reflections
5616 independent reflections
3997 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.127
S = 1.02
5616 reflections
343 parameters
346 restraints
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7O4ⁱ	0.93	2.48	3.333 (3)	153
C3-H3O8ⁱⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
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.
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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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Swaminathan, S. & Nigam, G. D. (1967). Curr. Sci. 36, 541.
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Yatsenko, A. V., Chernyshev, V. V., Popov, S. I., Sonneveld, E. J. & Schenk, H. (2000). Dyes Pigm. 45, 169-176.
Zielske, A. G. (1987). J. Org. Chem. 52, 1305-1309.

organic compounds