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Volume 66 
Part 8 
Pages m1036-m1037  
August 2010  

Received 30 June 2010
Accepted 25 July 2010
Online 31 July 2010

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Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.101
Data-to-parameter ratio = 10.4
Details
Open access

Sodium quercetin-8-sulfonate trihydrate

Xian Zhang,a Yueqing Li,a* Pingping Chen,a Tianjiao Hana and Weijie Zhaoa

aSchool of Pharmaceutical Science and Technology, Dalian Unversity of Technology, PO Box 90, Zhongshan Road 158, Dalian 116012, People's Republic of China
Correspondence e-mail: yueqingli@dlut.edu.cn

The organic anion of the title compound, {[Na(C15H9O10S)(H2O)2]·H2O}n {systematic name: poly[[diaqua[[mu]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4-oxo-4H-chromene-8-sulfonato]sodium] monohydrate]}, has a nearly planar structure. The Na atom is six-coordinated by O atoms, two from water molecules and four from the anion. The dihedral angle between the ring systems in the anion is 10.1 (1)°. Intramolecular O-H...S and O-H...O interactions occur. In the crystal structure, an extensive network of classical intermolecular O-H...S and O-H...O hydrogen bonds forms layers along the c axis.

Related literature

The title compound is of interest for its potential anti-inflammatory and antiviral properties. For the synthesis and structures of analogues of the title compound, see: Kopacz et al. (1978[Kopacz, M. & Nitka, B. (1978). Inst. Chem. Anal. (Wars.), 23, 343-349.], 1983[Kopacz, M., Nitka, B., Pusz, J. & Kopacz, S. (1983). Zh. Org. Khim. 19, 1681-1684.]); Cheng (2006[Cheng, X.-L. (2006). Masters Thesis, Shanxi Normal University, Xian, China.]); Wang (2007[Wang, Y.-C. (2007). Masters Thesis, Shanxi Normal University, Xian, China.]); Liu et al. (2009[Liu, B. & Yang, B.-L. (2009). Chin. J. Struct. Chem. 28, 1112-1120.]). For the anti-HIV properties of flavonoids and their derivatives, see: Kashiwada et al. (2005[Kashiwada Y., Aoshima A., Ikeshiro Y. & Chen, Y.-Pan. (2005). Bioorg. Med. Chem. 13, 443-448.]); Lameira et al. (2006[Lameira, J., Medeiros, I. G., Reis, M. & Santos, A. S. (2006). Bioorg. Med. Chem. 14, 7105-7112.]); Reutrakul et al. (2007[Reutrakul, V., Ningnuek, N., Pohmakotr, M. & Yoosook, C. (2007). Planta Med. 73, 683-688.]); Li et al. (2010[Li, Z.-L., Zhao, W.-J., Yang, Y.-S. & Li, Y.-Q. (2010). CN Patent CN101653437.]).

[Scheme 1]

Experimental

Crystal data

  • [Na(C15H9O10S)(H2O)2]·H2O

  • Mr = 458.33

  • Triclinic, [P \overline 1]

  • a = 7.595 (3) Å

  • b = 10.157 (3) Å

  • c = 12.183 (4) Å

  • [alpha] = 76.576 (4)°

  • [beta] = 81.031 (4)°

  • [gamma] = 77.385 (3)°

  • V = 886.6 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 295 K

  • 0.60 × 0.31 × 0.24 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • 4109 measured reflections

  • 2994 independent reflections

  • 2691 reflections with I > 2[sigma](I)

  • Rint = 0.013
Refinement

  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.101

  • S = 1.01

  • 2994 reflections

  • 289 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Selected bond lengths (Å)

Na1-O2i 2.3517 (16)
Na1-O6ii 2.3784 (16)
Na1-O1ii 2.3919 (17)
Na1-O13 2.4070 (18)
Na1-O12 2.555 (2)
Na1-O9 2.4074 (15)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y, z-1.

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O13iii 0.82 1.88 2.677 (2) 164
O4-H4A...O2i 0.82 1.97 2.786 (2) 170
O4-H4A...S1i 0.82 2.97 3.7139 (18) 152
O5-H5B...O9 0.82 1.89 2.619 (2) 148
O6-H6A...O12i 0.82 1.87 2.688 (2) 177
O8-H8B...O3 0.82 1.85 2.596 (2) 152
O8-H8B...S1 0.82 2.65 3.1344 (16) 120
O13-H13A...O11iv 0.85 (3) 1.95 (3) 2.799 (3) 174 (3)
O13-H13B...O7v 0.79 (3) 2.22 (3) 2.983 (2) 161 (3)
O13-H13B...O9 0.79 (3) 2.64 (3) 3.017 (2) 111 (2)
O13-H13B...S1v 0.79 (3) 3.02 (3) 3.7333 (18) 152 (3)
O12-H12A...O11vi 0.83 (3) 2.07 (3) 2.850 (3) 155 (3)
O12-H12B...O7i 0.90 (3) 1.87 (3) 2.767 (2) 172 (3)
O12-H12B...S1i 0.90 (3) 2.74 (3) 3.494 (2) 142 (2)
O11-H11A...O5vii 0.86 (4) 2.10 (4) 2.914 (3) 158 (3)
O11-H11B...O3 0.87 (4) 1.99 (4) 2.832 (2) 163 (3)
Symmetry codes: (i) -x+1, -y, -z+1; (iii) -x+1, -y+1, -z+1; (iv) x, y+1, z-1; (v) -x+2, -y, -z+1; (vi) x-1, y+1, z-1; (vii) -x+2, -y-1, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: RK2218 ).

Acknowledgements

We thank Dr Cheng He for his help during the refinement. This work was supported by the Fundamental Research Funds of the Central Universities of China.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Cheng, X.-L. (2006). Masters Thesis, Shanxi Normal University, Xian, China.
Kashiwada Y., Aoshima A., Ikeshiro Y. & Chen, Y.-Pan. (2005). Bioorg. Med. Chem. 13, 443-448.
Kopacz, M. & Nitka, B. (1978). Inst. Chem. Anal. (Wars.), 23, 343-349.
Kopacz, M., Nitka, B., Pusz, J. & Kopacz, S. (1983). Zh. Org. Khim. 19, 1681-1684.
Lameira, J., Medeiros, I. G., Reis, M. & Santos, A. S. (2006). Bioorg. Med. Chem. 14, 7105-7112.  [CrossRef] [PubMed]
Li, Z.-L., Zhao, W.-J., Yang, Y.-S. & Li, Y.-Q. (2010). CN Patent CN101653437.
Liu, B. & Yang, B.-L. (2009). Chin. J. Struct. Chem. 28, 1112-1120.
Reutrakul, V., Ningnuek, N., Pohmakotr, M. & Yoosook, C. (2007). Planta Med. 73, 683-688.  [ISI] [CrossRef] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, Y.-C. (2007). Masters Thesis, Shanxi Normal University, Xian, China.

Acta Cryst (2010). E66, m1036-m1037   [ doi:10.1107/S1600536810029570 ]

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