Acta Cryst. (2010). E66, m1036-m1037 [ doi:10.1107/S1600536810029570 ]
The organic anion of the title compound, {[Na(C15H9O10S)(H2O)2]·H2O}n {systematic name: poly[[diaqua[![[mu]](/logos/entities/mu_rmgif.gif)
-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-HO interactions occur. In the crystal structure, an extensive network of classical intermolecular O-HS and O-HO hydrogen bonds forms layers along the c axis.
The hydrogen atoms based on C were refined as riding on their parent atoms with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic H; H atoms of hydroxy groups with O—H = 0.82Å and Uiso(H) = 1.5Ueq(O). For H atoms of water molecules, positions were refined freely and Uiso(H) = 1.5Ueq(O).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./rk2218fig1thm.gif)
| Fig. 1. The synthetic route for title compound. |
![[Figure 2]](./rk2218fig2thm.gif)
| Fig. 2. The part of molecular structure of title compound, showing the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius. |
![[Figure 3]](./rk2218fig3thm.gif)
| Fig. 3. The oxygen environment of sodium cation. H atoms are omitted for clarity. Symmetry codes see in table of geometric parameters. |
![[Figure 4]](./rk2218fig4thm.gif)
| Fig. 4. A view of the packing of title compound. Dashed lines indicate O—H···O hydrogen bonds. |
| [Na(C15H9O10S)(H2O)2]·H2O | Z = 2 |
| Mr = 458.33 | F(000) = 472 |
| Triclinic, P1 | Dx = 1.717 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.595 (3) Å | Cell parameters from 3467 reflections |
| b = 10.157 (3) Å | θ = 2.3–26.2° |
| c = 12.183 (4) Å | µ = 0.28 mm−1 |
| α = 76.576 (4)° | T = 295 K |
| β = 81.031 (4)° | Needle, pale yellow |
| γ = 77.385 (3)° | 0.60 × 0.31 × 0.24 mm |
| V = 886.6 (5) Å3 |
| Bruker SMART APEX CCD diffractometer | 2691 reflections with I > 2σ(I) |
| Radiation source: fine–focus sealed tube | Rint = 0.013 |
| graphite | θmax = 25.0°, θmin = 2.4° |
| φ– and ω–scans | h = −9→8 |
| 4109 measured reflections | k = −12→10 |
| 2994 independent reflections | l = −14→9 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0667P)2 + 0.3015P] where P = (Fo2 + 2Fc2)/3 |
| 2994 reflections | (Δ/σ)max < 0.001 |
| 289 parameters | Δρmax = 0.24 e Å−3 |
| 0 restraints | Δρmin = −0.41 e Å−3 |
| [Na(C15H9O10S)(H2O)2]·H2O | γ = 77.385 (3)° |
| Mr = 458.33 | V = 886.6 (5) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.595 (3) Å | Mo Kα radiation |
| b = 10.157 (3) Å | µ = 0.28 mm−1 |
| c = 12.183 (4) Å | T = 295 K |
| α = 76.576 (4)° | 0.60 × 0.31 × 0.24 mm |
| β = 81.031 (4)° |
| Bruker SMART APEX CCD diffractometer | 2691 reflections with I > 2σ(I) |
| 4109 measured reflections | Rint = 0.013 |
| 2994 independent reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.101 | Δρmax = 0.24 e Å−3 |
| S = 1.01 | Δρmin = −0.41 e Å−3 |
| 2994 reflections | Absolute structure: ? |
| 289 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Experimental. The synthesis of title compound is shown in Fig. 1. The crude product was recrystallized by CH3OH/H2O = 3/1 in the yield of 60%. However, the single crystals were obtained in 0.9% NaCl aqueous solution at a concentration of 0.3 mg ml-1. |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F2, conventional R–factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R–factors(gt) etc. and is not relevant to the choice of reflections for refinement. R–factors based on F2 are statistically about twice as large as those based on F, and R–factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.91509 (6) | −0.29304 (4) | 0.71144 (4) | 0.02554 (15) | |
| O1 | 0.4645 (2) | 0.37543 (14) | 0.91755 (12) | 0.0410 (4) | |
| H1A | 0.4085 | 0.4545 | 0.8995 | 0.062* | |
| O2 | 0.72475 (18) | −0.29014 (14) | 0.75277 (11) | 0.0316 (3) | |
| O3 | 1.0212 (2) | −0.43287 (15) | 0.73041 (12) | 0.0423 (4) | |
| O4 | 0.5196 (2) | 0.27317 (13) | 0.40069 (11) | 0.0347 (3) | |
| H4A | 0.4517 | 0.2682 | 0.3563 | 0.052* | |
| O5 | 0.9040 (2) | −0.11772 (16) | 0.21432 (11) | 0.0427 (4) | |
| H5B | 0.8299 | −0.0458 | 0.2001 | 0.064* | |
| O6 | 0.6438 (2) | 0.11901 (14) | 0.94873 (11) | 0.0409 (4) | |
| H6A | 0.6838 | 0.0365 | 0.9526 | 0.061* | |
| O7 | 0.99190 (19) | −0.20151 (15) | 0.75754 (12) | 0.0373 (3) | |
| O8 | 1.14625 (18) | −0.43644 (14) | 0.52006 (12) | 0.0357 (3) | |
| H8B | 1.1330 | −0.4599 | 0.5895 | 0.054* | |
| O9 | 0.66041 (18) | 0.09603 (13) | 0.25617 (11) | 0.0308 (3) | |
| O10 | 0.74224 (17) | −0.02632 (12) | 0.58747 (10) | 0.0260 (3) | |
| C1 | 0.6350 (3) | 0.11097 (19) | 0.75271 (16) | 0.0276 (4) | |
| H1B | 0.6968 | 0.0200 | 0.7645 | 0.033* | |
| C2 | 0.9124 (3) | −0.1552 (2) | 0.32742 (16) | 0.0293 (4) | |
| C3 | 0.4925 (3) | 0.31432 (19) | 0.62889 (16) | 0.0297 (4) | |
| H3B | 0.4576 | 0.3606 | 0.5580 | 0.036* | |
| C4 | 0.5007 (3) | 0.31472 (19) | 0.82552 (16) | 0.0296 (4) | |
| C5 | 0.4522 (3) | 0.38082 (19) | 0.71898 (17) | 0.0317 (4) | |
| H5A | 0.3912 | 0.4720 | 0.7077 | 0.038* | |
| C6 | 0.5936 (3) | 0.17823 (19) | 0.84191 (16) | 0.0280 (4) | |
| C7 | 1.0321 (2) | −0.31769 (18) | 0.48751 (16) | 0.0267 (4) | |
| C8 | 1.0238 (3) | −0.2759 (2) | 0.37051 (17) | 0.0314 (4) | |
| H8A | 1.0939 | −0.3301 | 0.3217 | 0.038* | |
| C9 | 0.8119 (2) | −0.06762 (18) | 0.39941 (15) | 0.0244 (4) | |
| C10 | 0.8272 (2) | −0.10881 (18) | 0.51493 (15) | 0.0239 (4) | |
| C11 | 0.5857 (2) | 0.17729 (18) | 0.64382 (15) | 0.0238 (4) | |
| C12 | 0.6164 (2) | 0.14599 (18) | 0.43889 (15) | 0.0250 (4) | |
| C13 | 0.6439 (2) | 0.10360 (18) | 0.55063 (15) | 0.0239 (4) | |
| C14 | 0.6942 (2) | 0.05993 (18) | 0.35794 (15) | 0.0241 (4) | |
| C15 | 0.9291 (2) | −0.23665 (18) | 0.56233 (15) | 0.0245 (4) | |
| Na1 | 0.49543 (10) | 0.22781 (8) | 0.10033 (6) | 0.0340 (2) | |
| O13 | 0.7175 (2) | 0.36463 (15) | 0.09986 (14) | 0.0366 (3) | |
| H13A | 0.790 (4) | 0.362 (3) | 0.039 (2) | 0.055* | |
| H13B | 0.776 (4) | 0.325 (3) | 0.150 (2) | 0.055* | |
| O12 | 0.2274 (2) | 0.15022 (17) | 0.04739 (15) | 0.0459 (4) | |
| H12A | 0.182 (4) | 0.209 (3) | −0.006 (3) | 0.069* | |
| H12B | 0.151 (4) | 0.161 (3) | 0.110 (3) | 0.069* | |
| O11 | 0.9733 (3) | −0.6600 (2) | 0.91012 (15) | 0.0564 (5) | |
| H11A | 0.982 (5) | −0.731 (4) | 0.882 (3) | 0.085* | |
| H11B | 0.986 (5) | −0.582 (4) | 0.866 (3) | 0.085* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0235 (3) | 0.0283 (3) | 0.0212 (3) | −0.00011 (18) | −0.00574 (18) | −0.00029 (18) |
| O1 | 0.0618 (10) | 0.0307 (7) | 0.0262 (8) | 0.0075 (7) | −0.0099 (7) | −0.0089 (6) |
| O2 | 0.0257 (7) | 0.0430 (8) | 0.0247 (7) | −0.0058 (6) | −0.0031 (5) | −0.0045 (6) |
| O3 | 0.0463 (9) | 0.0363 (8) | 0.0297 (8) | 0.0110 (7) | −0.0030 (6) | 0.0039 (6) |
| O4 | 0.0476 (9) | 0.0261 (7) | 0.0292 (7) | 0.0043 (6) | −0.0207 (6) | −0.0031 (6) |
| O5 | 0.0553 (10) | 0.0449 (8) | 0.0197 (7) | 0.0086 (7) | −0.0050 (6) | −0.0063 (6) |
| O6 | 0.0618 (10) | 0.0324 (7) | 0.0219 (7) | 0.0103 (7) | −0.0124 (7) | −0.0051 (6) |
| O7 | 0.0377 (8) | 0.0490 (9) | 0.0286 (7) | −0.0148 (7) | −0.0095 (6) | −0.0045 (6) |
| O8 | 0.0338 (8) | 0.0335 (7) | 0.0316 (8) | 0.0091 (6) | −0.0045 (6) | −0.0042 (6) |
| O9 | 0.0346 (7) | 0.0344 (7) | 0.0214 (7) | −0.0050 (6) | −0.0085 (6) | 0.0002 (6) |
| O10 | 0.0303 (7) | 0.0240 (6) | 0.0201 (6) | 0.0031 (5) | −0.0057 (5) | −0.0027 (5) |
| C1 | 0.0314 (10) | 0.0235 (9) | 0.0250 (10) | −0.0009 (7) | −0.0059 (8) | −0.0016 (7) |
| C2 | 0.0290 (10) | 0.0354 (10) | 0.0215 (9) | −0.0047 (8) | −0.0025 (7) | −0.0035 (8) |
| C3 | 0.0321 (10) | 0.0292 (10) | 0.0253 (10) | 0.0012 (8) | −0.0099 (8) | −0.0028 (8) |
| C4 | 0.0311 (10) | 0.0292 (10) | 0.0280 (10) | −0.0023 (8) | −0.0045 (8) | −0.0073 (8) |
| C5 | 0.0347 (11) | 0.0266 (9) | 0.0299 (10) | 0.0041 (8) | −0.0083 (8) | −0.0041 (8) |
| C6 | 0.0317 (10) | 0.0293 (10) | 0.0205 (9) | −0.0021 (8) | −0.0070 (7) | −0.0008 (8) |
| C7 | 0.0220 (9) | 0.0277 (9) | 0.0286 (10) | −0.0020 (7) | −0.0034 (7) | −0.0040 (8) |
| C8 | 0.0304 (10) | 0.0341 (10) | 0.0270 (10) | −0.0008 (8) | 0.0010 (8) | −0.0088 (8) |
| C9 | 0.0232 (9) | 0.0268 (9) | 0.0225 (9) | −0.0058 (7) | −0.0040 (7) | −0.0015 (7) |
| C10 | 0.0211 (9) | 0.0268 (9) | 0.0230 (9) | −0.0041 (7) | −0.0021 (7) | −0.0046 (7) |
| C11 | 0.0226 (9) | 0.0245 (9) | 0.0244 (9) | −0.0048 (7) | −0.0051 (7) | −0.0031 (7) |
| C12 | 0.0241 (9) | 0.0244 (9) | 0.0258 (9) | −0.0048 (7) | −0.0074 (7) | −0.0005 (7) |
| C13 | 0.0213 (9) | 0.0222 (8) | 0.0266 (10) | −0.0025 (7) | −0.0064 (7) | −0.0007 (7) |
| C14 | 0.0219 (9) | 0.0285 (9) | 0.0219 (9) | −0.0092 (7) | −0.0044 (7) | 0.0004 (7) |
| C15 | 0.0223 (9) | 0.0269 (9) | 0.0224 (9) | −0.0029 (7) | −0.0040 (7) | −0.0023 (7) |
| Na1 | 0.0363 (4) | 0.0398 (4) | 0.0239 (4) | −0.0026 (3) | −0.0038 (3) | −0.0064 (3) |
| O13 | 0.0419 (9) | 0.0356 (8) | 0.0295 (8) | −0.0001 (6) | −0.0124 (6) | −0.0025 (6) |
| O12 | 0.0565 (10) | 0.0388 (8) | 0.0330 (9) | 0.0063 (7) | −0.0072 (8) | −0.0014 (7) |
| O11 | 0.0839 (14) | 0.0463 (10) | 0.0333 (9) | −0.0074 (9) | −0.0062 (9) | −0.0016 (8) |
| S1—O7 | 1.4498 (15) | C3—C11 | 1.401 (3) |
| S1—O2 | 1.4510 (15) | C3—H3B | 0.9300 |
| S1—O3 | 1.4581 (15) | C4—C5 | 1.381 (3) |
| S1—C15 | 1.7671 (19) | C4—C6 | 1.396 (3) |
| O1—C4 | 1.365 (2) | C5—H5A | 0.9300 |
| O1—Na1i | 2.3919 (17) | C7—C8 | 1.397 (3) |
| O1—H1A | 0.8200 | C7—C15 | 1.402 (3) |
| O2—Na1ii | 2.3517 (16) | C8—H8A | 0.9300 |
| O4—C12 | 1.356 (2) | C9—C10 | 1.388 (3) |
| O4—H4A | 0.8200 | C9—C14 | 1.437 (3) |
| O5—C2 | 1.349 (2) | C10—C15 | 1.404 (2) |
| O5—H5B | 0.8200 | C11—C13 | 1.462 (3) |
| O6—C6 | 1.375 (2) | C12—C13 | 1.364 (3) |
| O6—Na1i | 2.3784 (16) | C12—C14 | 1.442 (3) |
| O6—H6A | 0.8200 | Na1—O2ii | 2.3517 (16) |
| O8—C7 | 1.339 (2) | Na1—O6iii | 2.3784 (16) |
| O8—H8B | 0.8200 | Na1—O1iii | 2.3919 (17) |
| O9—C14 | 1.259 (2) | Na1—O13 | 2.4070 (18) |
| O9—Na1 | 2.4074 (15) | Na1—O12 | 2.555 (2) |
| O10—C10 | 1.353 (2) | Na1—O9 | 2.4074 (15) |
| O10—C13 | 1.378 (2) | O13—H13A | 0.85 (3) |
| C1—C6 | 1.375 (3) | O13—H13B | 0.79 (3) |
| C1—C11 | 1.409 (3) | O12—H12A | 0.83 (3) |
| C1—H1B | 0.9300 | O12—H12B | 0.90 (3) |
| C2—C8 | 1.371 (3) | O11—H11A | 0.86 (4) |
| C2—C9 | 1.414 (3) | O11—H11B | 0.87 (4) |
| C3—C5 | 1.380 (3) | ||
| O7—S1—O2 | 112.09 (8) | C10—C9—C14 | 119.29 (16) |
| O7—S1—O3 | 111.69 (9) | C2—C9—C14 | 122.76 (17) |
| O2—S1—O3 | 111.94 (9) | O10—C10—C9 | 120.78 (16) |
| O7—S1—C15 | 108.31 (8) | O10—C10—C15 | 116.87 (16) |
| O2—S1—C15 | 107.22 (8) | C9—C10—C15 | 122.35 (17) |
| O3—S1—C15 | 105.18 (8) | C3—C11—C1 | 117.98 (16) |
| C4—O1—Na1i | 117.41 (12) | C3—C11—C13 | 123.15 (16) |
| C4—O1—H1A | 109.5 | C1—C11—C13 | 118.75 (16) |
| Na1i—O1—H1A | 130.6 | O4—C12—C13 | 120.25 (16) |
| S1—O2—Na1ii | 141.71 (9) | O4—C12—C14 | 118.36 (15) |
| C12—O4—H4A | 109.5 | C13—C12—C14 | 121.35 (16) |
| C2—O5—H5B | 109.5 | C12—C13—O10 | 119.16 (16) |
| C6—O6—Na1i | 117.44 (11) | C12—C13—C11 | 129.68 (16) |
| C6—O6—H6A | 109.5 | O10—C13—C11 | 111.15 (15) |
| Na1i—O6—H6A | 126.9 | O9—C14—C9 | 122.20 (17) |
| C7—O8—H8B | 109.5 | O9—C14—C12 | 121.20 (16) |
| C14—O9—Na1 | 155.71 (12) | C9—C14—C12 | 116.61 (16) |
| C10—O10—C13 | 122.23 (14) | C7—C15—C10 | 117.60 (17) |
| C6—C1—C11 | 121.25 (16) | C7—C15—S1 | 122.63 (14) |
| C6—C1—H1B | 119.4 | C10—C15—S1 | 119.70 (14) |
| C11—C1—H1B | 119.4 | O2ii—Na1—O6iii | 160.25 (6) |
| O5—C2—C8 | 119.29 (17) | O2ii—Na1—O1iii | 115.40 (6) |
| O5—C2—C9 | 119.81 (17) | O6iii—Na1—O1iii | 67.01 (5) |
| C8—C2—C9 | 120.86 (17) | O2ii—Na1—O13 | 102.00 (6) |
| C5—C3—C11 | 120.22 (17) | O6iii—Na1—O13 | 97.74 (6) |
| C5—C3—H3B | 119.9 | O1iii—Na1—O13 | 81.25 (6) |
| C11—C3—H3B | 119.9 | O2ii—Na1—O9 | 82.95 (6) |
| O1—C4—C5 | 123.83 (17) | O6iii—Na1—O9 | 101.98 (6) |
| O1—C4—C6 | 116.98 (17) | O1iii—Na1—O9 | 154.60 (6) |
| C5—C4—C6 | 119.19 (17) | O13—Na1—O9 | 77.62 (6) |
| C3—C5—C4 | 121.35 (17) | O2ii—Na1—O12 | 81.05 (6) |
| C3—C5—H5A | 119.3 | O6iii—Na1—O12 | 80.12 (6) |
| C4—C5—H5A | 119.3 | O1iii—Na1—O12 | 80.40 (6) |
| C1—C6—O6 | 123.26 (16) | O13—Na1—O12 | 160.82 (6) |
| C1—C6—C4 | 120.01 (17) | O9—Na1—O12 | 121.53 (6) |
| O6—C6—C4 | 116.70 (16) | Na1—O13—H13A | 107.5 (19) |
| O8—C7—C8 | 115.11 (16) | Na1—O13—H13B | 106 (2) |
| O8—C7—C15 | 124.11 (17) | H13A—O13—H13B | 106 (3) |
| C8—C7—C15 | 120.77 (17) | Na1—O12—H12A | 109 (2) |
| C2—C8—C7 | 120.17 (17) | Na1—O12—H12B | 98.1 (19) |
| C2—C8—H8A | 119.9 | H12A—O12—H12B | 106 (3) |
| C7—C8—H8A | 119.9 | H11A—O11—H11B | 120 (3) |
| C10—C9—C2 | 117.94 (16) |
| Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z+1; (iii) x, y, z−1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1A···O13iv | 0.82 | 1.88 | 2.677 (2) | 164 |
| O4—H4A···O2ii | 0.82 | 1.97 | 2.786 (2) | 170 |
| O4—H4A···S1ii | 0.82 | 2.97 | 3.7139 (18) | 152 |
| O5—H5B···O9 | 0.82 | 1.89 | 2.619 (2) | 148 |
| O6—H6A···O12ii | 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···O11v | 0.85 (3) | 1.95 (3) | 2.799 (3) | 174 (3) |
| O13—H13B···O7vi | 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···S1vi | 0.79 (3) | 3.02 (3) | 3.7333 (18) | 152 (3) |
| O12—H12A···O11vii | 0.83 (3) | 2.07 (3) | 2.850 (3) | 155 (3) |
| O12—H12B···O7ii | 0.90 (3) | 1.87 (3) | 2.767 (2) | 172 (3) |
| O12—H12B···S1ii | 0.90 (3) | 2.74 (3) | 3.494 (2) | 142 (2) |
| O11—H11A···O5viii | 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: (iv) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (v) x, y+1, z−1; (vi) −x+2, −y, −z+1; (vii) x−1, y+1, z−1; (viii) −x+2, −y−1, −z+1. |
| Na1—O2i | 2.3517 (16) | Na1—O13 | 2.4070 (18) |
| Na1—O6ii | 2.3784 (16) | Na1—O12 | 2.555 (2) |
| Na1—O1ii | 2.3919 (17) | Na1—O9 | 2.4074 (15) |
| Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z−1. |
| 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: (iii) −x+1, −y+1, −z+1; (i) −x+1, −y, −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. |
We thank Dr Cheng He for his help during the refinement. This work wass supported by the Fundamental Research Funds of the Central University.
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The flavonoids and their derivants have been investigated for a long time for their notable antiviral activity especially against HIV-1 (Kashiwada et al., 2005; Lameira et al., 2006; Reutrakul et al., 2007). A great many of substituents have been applied to modify the structures to develop their solubility in water such as sulfonic group (Cheng, 2006; Kopacz, et al., 1978; Kopacz et al., 1983; Liu et al., 2009; Wang, 2007). The title compound is an excellent antagonist of Vif which has been found to be a novel hit of HIV–1 (Li et al., 2010). The crystal structure of the title compound may be helpful to the understanding of quantitative structure–activity relationship.
Quercetin–8–sulfonate sodium is synthesized from quercetin via sulfonation (Fig.1). The asymmetric unit of the title compound contains a quercetin–8–sulfonic anion, a sodium cation and three molecules of water (Fig.2). The anion structure is nearly coplanar.
In the crystal structure, sodium cation form six contacts 2.392 (2)–2.555 (2)Å (Fig.3) with oxygen atoms: two water atoms and four with other atoms of anion.
The hydrogen bonds assist crystal packing in layers along the c axis, (Table 1, Fig. 4).