Sodium quercetin-8-sulfonate trihydrate.

The organic anion of the title compound, {[Na(C(15)H(9)O(10)S)(H(2)O)(2)]·H(2)O}(n) {systematic name: poly[[diaqua-[μ-2-(3,4-dihy-droxy-phen-yl)-3,5,7-trihy-droxy-4-oxo-4H-chromene-8-sulfon-ato]-sodium] monohydrate]}, has a nearly planar structure. The Na atom is six-coordinated by O atoms, two from water mol-ecules and four from the anion. The dihedral angle between the ring systems in the anion is 10.1 (1)°. Intra-molecular O-H⋯S and O-H⋯O inter-actions occur. In the crystal structure, an extensive network of classical inter-molecular 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 ▶, 1983 ▶); Cheng (2006 ▶); Wang (2007 ▶); Liu et al. (2009 ▶). For the anti-HIV properties of flavonoids and their derivatives, see: Kashiwada et al. (2005 ▶); Lameira et al. (2006 ▶); Reutrakul et al. (2007 ▶); Li et al. (2010 ▶).

Experimental

Crystal data

[Na(C15H9O10S)(H2O)2]·H2O

M = 458.33

Triclinic,

a = 7.595 (3) Å

b = 10.157 (3) Å

c = 12.183 (4) Å

α = 76.576 (4)°

β = 81.031 (4)°

γ = 77.385 (3)°

V = 886.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.101

S = 1.01

2994 reflections

289 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810029570/rk2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029570/rk2218Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[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

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)

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)

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) ; (ii) .

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) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .