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Volume 69 
Part 7 
Page o1172  
July 2013  

Received 7 June 2013
Accepted 23 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.059
wR = 0.146
Data-to-parameter ratio = 13.9
Details
Open access

N,N'-Diphenyl-9,10-dioxo-9,10-dihydroanthracene-2,7-disulfonamide

aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, School of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
Correspondence e-mail: yuanweiguan_1@cwnu.edu.cn

The title molecule, C26H18N2O6S2, has an overall Z-shaped conformation, in which the benzene rings are inclined to the anthraquinone mean plane by 60.60 (9) and 50.66 (13)°. In the crystal, N-H...O and C-H...O hydrogen bonds link the molecules into layers parallel to the bc plane.

Related literature

For applications of sulfonamide derivitives, see: Valeur & Leray (2000[Valeur, B. & Leray, I. (2000). Coord Chem. Rev. 205, 3-40.]); Chen et al. (2000[Chen, L. P., Yang, L. T., Li, H. W., Gao, Y., Deng, D. Y., Wu, Y. Q. & Ma, L. J. (2000). Inorg. Chem. 50, 10028-0032.]); Kuljit & Subodh (2011[Kuljit, K. & Subodh, K. (2011). Dalton Trans. 40, 2451-2458.]). For applications of anthraquinone derivitives, see: Lu et al. (2006[Lu, Z. K., Lord, S. J., Wang, H., Moerner, W. E. & Twieg, R. J. (2006). J. Org. Chem. 71, 9651-9657.]); Liu et al. (2011[Liu, Y. L., Sun, Y., Du, J., Lv, X., Zhao, Y., Chen, M. L., Wang, P. & Guo, W. (2011). Org. Biomol. Chem. 9, 432-437.]). For details of the synthesis, see: Kuljit & Subodh (2011[Kuljit, K. & Subodh, K. (2011). Dalton Trans. 40, 2451-2458.]); Zeng & King (2002[Zeng, B. B. & King, S. B. (2002). Synthesis, 16, 2335-2337.]). For a related structure, see: Li et al. (2009[Li, H. W., Li, Y., Dang, Y. Q., Ma, L. J., Wu, Y. Q. & Hou, G. F. (2009). Chem. Commun. 29, 4453-4455.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C26H18N2O6S2

  • Mr = 518.54

  • Monoclinic, P 21 /c

  • a = 10.247 (4) Å

  • b = 6.395 (2) Å

  • c = 36.265 (12) Å

  • [beta] = 104.511 (12)°

  • V = 2300.6 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 293 K

  • 0.26 × 0.17 × 0.14 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 = 0.931, Tmax = 0.962

  • 12233 measured reflections

  • 4512 independent reflections

  • 1965 reflections with I > 2[sigma](I)

  • Rint = 0.088

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.146

  • S = 1.00

  • 4512 reflections

  • 325 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2B...O4i 0.86 2.55 3.110 (4) 123
N1-H1B...O2ii 0.86 2.32 2.952 (5) 131
C19-H19A...O6iii 0.93 2.35 3.164 (5) 146
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y+3, -z+2.

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: 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: CV5417 ).


Acknowledgements

The authors thank the Scientific Researching Fund Projects of China West Normal University (grant No. 06B003).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, L. P., Yang, L. T., Li, H. W., Gao, Y., Deng, D. Y., Wu, Y. Q. & Ma, L. J. (2000). Inorg. Chem. 50, 10028-0032.
Kuljit, K. & Subodh, K. (2011). Dalton Trans. 40, 2451-2458.  [PubMed]
Li, H. W., Li, Y., Dang, Y. Q., Ma, L. J., Wu, Y. Q. & Hou, G. F. (2009). Chem. Commun. 29, 4453-4455.  [CrossRef]
Liu, Y. L., Sun, Y., Du, J., Lv, X., Zhao, Y., Chen, M. L., Wang, P. & Guo, W. (2011). Org. Biomol. Chem. 9, 432-437.  [CrossRef] [ChemPort] [PubMed]
Lu, Z. K., Lord, S. J., Wang, H., Moerner, W. E. & Twieg, R. J. (2006). J. Org. Chem. 71, 9651-9657.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Valeur, B. & Leray, I. (2000). Coord Chem. Rev. 205, 3-40.  [CrossRef] [ChemPort]
Zeng, B. B. & King, S. B. (2002). Synthesis, 16, 2335-2337.


Acta Cryst (2013). E69, o1172  [ doi:10.1107/S1600536813017303 ]

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