Disodium 4,5,6-trihy-droxy-benzene-1,3-disulfonate dihydrate.

In the title compound, 2Na(+)·C(6)H(4)O(9)S(2) (2-)·2H(2)O, the benzene rings of the 4,5,6-trihy-droxy-benzene-1,3-disulfonate ions, which are stacked parallel to each other forming rods parallel to the a axis, are slightly deformed (planarity, symmetry) mainly because of the high degree of substitution. The two sodium ions, located within pockets of the anion rods, are coordinated by six and seven O atoms, resulting in octa-hedral and penta-gonal-bipyramidal coordinations, respectively. In addition to these coordinative bonds towards sodium, an extended network of intra- and inter-molecular hydrogen bonds occurs.

Related literature

For synthetic procedures for 3,4,5-trihy­droxy­benzene­sulfonic acid, see: Pješčić et al. (2000 ▶). For the properties and application of cunitic (i.e. wedge-shaped, amphiphilic) gelator molecules,, see: Beginn et al. (2008 ▶); Zhu et al. (2004 ▶, 2006 ▶); Percec et al. (2004 ▶, 2006 ▶). For oxidation processes of pyrogallol, see: Siegel & Siegel (1950 ▶).

Experimental

Crystal data

2Na+·C6H4O9S2 2−·2H2O

M = 366.22

Triclinic,

a = 6.9282 (4) Å

b = 9.1952 (5) Å

c = 10.6171 (6) Å

α = 68.303 (3)°

β = 75.984 (3)°

γ = 68.455 (2)°

V = 580.10 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.60 mm−1

T = 100 K

0.31 × 0.08 × 0.06 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.839, T max = 0.965

24130 measured reflections

2000 independent reflections

1735 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.065

S = 1.09

2000 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.40 e Å−3

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: DIAMOND (Brandenburg, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036160/im2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036160/im2221Isup2.hkl

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

2Na+·C6H4O9S22−·2H2O	Z = 2
Mr = 366.22	F(000) = 372
Triclinic, P1	Dx = 2.097 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9282 (4) Å	Cell parameters from 9296 reflections
b = 9.1952 (5) Å	θ = 2.7–27.8°
c = 10.6171 (6) Å	µ = 0.60 mm−1
α = 68.303 (3)°	T = 100 K
β = 75.984 (3)°	Needle, red
γ = 68.455 (2)°	0.31 × 0.08 × 0.06 mm
V = 580.10 (6) Å3

Bruker APEXII diffractometer	2000 independent reflections
Radiation source: fine-focus sealed tube	1735 reflections with I > 2σ(I)
graphite	Rint = 0.041
phi and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
Tmin = 0.839, Tmax = 0.965	k = −10→10
24130 measured reflections	l = −12→12

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0278P)2 + 0.5372P] where P = (Fo2 + 2Fc2)/3
2000 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
C1	0.1954 (3)	0.5924 (3)	0.1388 (2)	0.0094 (5)
C2	0.1960 (3)	0.4422 (3)	0.2347 (2)	0.0103 (5)
H2	0.1730	0.4321	0.3291	0.025 (4)*
C3	0.2296 (3)	0.3064 (3)	0.1960 (2)	0.0087 (4)
C4	0.2534 (3)	0.3218 (3)	0.0577 (2)	0.0085 (4)
C5	0.2577 (3)	0.4724 (3)	−0.0403 (2)	0.0093 (5)
C6	0.2323 (3)	0.6076 (3)	−0.0004 (2)	0.0092 (5)
O4	0.2764 (2)	0.19739 (17)	0.00969 (14)	0.0109 (3)
H4	0.2447	0.1257	0.0723	0.025 (4)*
O5	0.2915 (2)	0.47596 (18)	−0.17322 (14)	0.0114 (3)
H5	0.2801	0.5660	−0.2260	0.025 (4)*
O6	0.2426 (2)	0.75022 (17)	−0.10051 (14)	0.0120 (3)
H6	0.2476	0.8099	−0.0635	0.025 (4)*
S1	0.15178 (8)	0.75784 (6)	0.20027 (5)	0.00896 (14)
O11	−0.0728 (2)	0.83560 (18)	0.21945 (15)	0.0144 (3)
O12	0.2449 (3)	0.68521 (18)	0.32711 (16)	0.0173 (4)
O13	0.2611 (2)	0.86540 (18)	0.09335 (15)	0.0163 (4)
S3	0.25656 (8)	0.11379 (6)	0.32262 (5)	0.00844 (14)
O31	0.1976 (2)	0.14814 (18)	0.45258 (15)	0.0148 (4)
O32	0.4746 (2)	0.01570 (18)	0.30296 (15)	0.0124 (3)
O33	0.1180 (2)	0.04470 (18)	0.29754 (15)	0.0140 (4)
Na1	−0.21766 (13)	1.04339 (10)	0.32841 (8)	0.0108 (2)
Na2	0.59706 (14)	0.77666 (10)	0.22482 (8)	0.0142 (2)
O1	−0.2793 (3)	1.26461 (18)	0.40886 (15)	0.0164 (4)
H11	−0.3886	1.2910	0.4554	0.045 (5)*
H12	−0.1912	1.2450	0.4555	0.045 (5)*
O2	0.6746 (3)	0.62770 (19)	0.45172 (16)	0.0196 (4)
H21	0.7198	0.5353	0.5011	0.045 (5)*
H22	0.7376	0.6789	0.4635	0.045 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0076 (11)	0.0091 (11)	0.0130 (11)	−0.0014 (9)	−0.0017 (9)	−0.0059 (9)
C2	0.0107 (11)	0.0120 (11)	0.0087 (11)	−0.0023 (10)	−0.0006 (9)	−0.0054 (9)
C3	0.0064 (11)	0.0092 (11)	0.0098 (10)	−0.0016 (9)	−0.0010 (8)	−0.0030 (9)
C4	0.0051 (10)	0.0084 (11)	0.0133 (11)	−0.0009 (9)	−0.0011 (8)	−0.0059 (9)
C5	0.0069 (11)	0.0132 (11)	0.0087 (11)	−0.0024 (9)	−0.0008 (8)	−0.0053 (9)
C6	0.0042 (10)	0.0092 (11)	0.0127 (11)	−0.0011 (9)	−0.0011 (8)	−0.0028 (9)
O4	0.0170 (8)	0.0074 (7)	0.0102 (7)	−0.0061 (7)	0.0003 (6)	−0.0037 (6)
O5	0.0191 (8)	0.0080 (8)	0.0070 (7)	−0.0044 (7)	−0.0014 (6)	−0.0021 (6)
O6	0.0189 (9)	0.0084 (8)	0.0106 (8)	−0.0059 (7)	−0.0016 (6)	−0.0035 (6)
S1	0.0108 (3)	0.0075 (3)	0.0104 (3)	−0.0026 (2)	−0.0010 (2)	−0.0052 (2)
O11	0.0111 (8)	0.0151 (8)	0.0218 (9)	−0.0033 (7)	−0.0005 (6)	−0.0129 (7)
O12	0.0253 (9)	0.0109 (8)	0.0181 (8)	−0.0005 (7)	−0.0111 (7)	−0.0071 (7)
O13	0.0224 (9)	0.0138 (8)	0.0161 (8)	−0.0104 (7)	0.0049 (7)	−0.0081 (7)
S3	0.0103 (3)	0.0072 (3)	0.0087 (3)	−0.0028 (2)	−0.0011 (2)	−0.0033 (2)
O31	0.0238 (9)	0.0114 (8)	0.0091 (8)	−0.0051 (7)	−0.0012 (7)	−0.0042 (6)
O32	0.0091 (8)	0.0099 (8)	0.0182 (8)	−0.0014 (7)	−0.0028 (6)	−0.0053 (6)
O33	0.0125 (8)	0.0109 (8)	0.0212 (9)	−0.0044 (7)	−0.0026 (7)	−0.0066 (7)
Na1	0.0119 (4)	0.0103 (4)	0.0115 (4)	−0.0041 (4)	−0.0011 (3)	−0.0045 (3)
Na2	0.0184 (5)	0.0132 (4)	0.0135 (4)	−0.0051 (4)	0.0000 (4)	−0.0079 (4)
O1	0.0215 (9)	0.0143 (8)	0.0144 (8)	−0.0044 (7)	−0.0027 (7)	−0.0062 (7)
O2	0.0266 (10)	0.0156 (9)	0.0191 (9)	−0.0084 (8)	−0.0093 (7)	−0.0025 (7)

C1—C2	1.380 (3)	S1—O11	1.4530 (16)
C2—C3	1.379 (3)	S1—O12	1.4545 (16)
C3—C4	1.396 (3)	S1—O13	1.4644 (15)
C4—C5	1.397 (3)	O11—Na1	2.3791 (17)
C5—C6	1.396 (3)	O12—Na2	2.7178 (18)
C6—C1	1.399 (3)	O13—Na2	2.7143 (18)
C1—S1	1.770 (2)	S3—O33	1.4465 (15)
C2—H2	0.9500	S3—O31	1.4577 (16)
C3—S3	1.760 (2)	S3—O32	1.4579 (15)
C4—O4	1.361 (3)	Na1—O1	2.3495 (17)
C5—O5	1.363 (2)	Na2—O2	2.3695 (17)
C6—O6	1.363 (2)	O1—H11	0.8056
O4—H4	0.7979	O1—H12	0.8056
O5—H5	0.7979	O2—H21	0.8056
O6—H6	0.7980	O2—H22	0.8056
C2—C1—C6	119.77 (19)	C1—S1—Na2	109.02 (7)
C2—C1—S1	117.18 (16)	S1—O11—Na1	120.84 (8)
C6—C1—S1	123.04 (16)	S1—O12—Na2	96.74 (8)
C3—C2—C1	121.12 (19)	S1—O13—Na2	96.63 (8)
C3—C2—H2	119.4	O33—S3—O31	113.52 (9)
C1—C2—H2	119.4	O33—S3—O32	111.33 (9)
C4—C3—C2	119.84 (19)	O31—S3—O32	113.24 (9)
C2—C3—S3	118.86 (16)	O33—S3—C3	106.02 (9)
C4—C3—S3	121.20 (16)	O31—S3—C3	105.58 (10)
O4—C4—C3	124.23 (18)	O32—S3—C3	106.43 (9)
O4—C4—C5	116.35 (18)	O1—Na1—O11	165.05 (6)
C5—C4—C3	119.41 (19)	O1—Na1—S1	144.75 (5)
O5—C5—C6	123.60 (18)	O11—Na1—S1	21.77 (4)
O5—C5—C4	116.09 (19)	O2—Na2—O13	134.47 (6)
C6—C5—C4	120.30 (19)	O2—Na2—O12	81.64 (5)
O6—C6—C5	117.69 (18)	O13—Na2—O12	53.02 (5)
O6—C6—C1	122.94 (19)	O2—Na2—S1	108.18 (5)
C1—C6—C5	119.37 (19)	O13—Na2—S1	26.77 (3)
C4—O4—H4	107.7	O12—Na2—S1	26.57 (3)
C5—O5—H5	113.1	O2—Na2—H22	17.3
C6—O6—H6	106.5	O13—Na2—H22	146.5
O11—S1—O12	113.02 (9)	O12—Na2—H22	96.0
O11—S1—O13	112.95 (9)	S1—Na2—H22	122.3
O12—S1—O13	112.34 (9)	Na1—O1—H11	117.6
O11—S1—C1	107.38 (9)	Na1—O1—H12	110.7
O12—S1—C1	105.84 (9)	H11—O1—H12	104.6
O13—S1—C1	104.55 (9)	Na2—O2—H21	141.7
O11—S1—Na2	143.60 (6)	Na2—O2—H22	101.8
O12—S1—Na2	56.69 (7)	H21—O2—H22	104.6
O13—S1—Na2	56.60 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O33	0.80	2.28	2.975 (2)	146
O4—H4···O13i	0.80	2.28	2.882 (2)	133
O5—H5···O1ii	0.80	1.99	2.738 (2)	156
O6—H6···O13	0.80	1.94	2.686 (2)	154
O1—H11···O2iii	0.81	1.99	2.793 (2)	173
O1—H12···O31iv	0.81	2.50	3.171 (2)	141
O1—H12···O12iii	0.81	2.53	3.080 (2)	127
O2—H21···O12v	0.81	2.15	2.926 (2)	162
O2—H22···O31v	0.81	2.30	3.064 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O33	0.80	2.28	2.975 (2)	146
O4—H4⋯O13i	0.80	2.28	2.882 (2)	133
O5—H5⋯O1ii	0.80	1.99	2.738 (2)	156
O6—H6⋯O13	0.80	1.94	2.686 (2)	154
O1—H11⋯O2iii	0.81	1.99	2.793 (2)	173
O1—H12⋯O31iv	0.81	2.50	3.171 (2)	141
O1—H12⋯O12iii	0.81	2.53	3.080 (2)	127
O2—H21⋯O12v	0.81	2.15	2.926 (2)	162
O2—H22⋯O31v	0.81	2.30	3.064 (2)	159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .