Disodium 2,2′-dithio­bis(ethanesulfonate) trihydrate (dimesna trihydrate)

Bambagiotti-Alberti, M.; Bartolucci, G.; Bruni, B.; Di Vaira, M.; Passaponti, M.

doi:10.1107/S1600536807029273

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Disodium 2,2′-dithiobis(ethanesulfonate) trihydrate (dimesna trihydrate)

M. Bambagiotti-Alberti, G. Bartolucci, B. Bruni, M. Di Vaira and M. Passaponti

The structure of the title compound, poly[[di-μ-aqua-μ₄-[2,2′-dithiobis(ethanesulfonato)]-disodium(I)] monohydrate], {[Na₂(C₄H₈O₆S₄)(H₂O)₂]·H₂O}_n, otherwise known as dimesna trihydrate, exhibits layers formed by the anions parallel to the ab face, connected by layers formed by the Na⁺ cations and coordinating water molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029273/tk2163sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029273/tk2163Isup2.hkl Contains datablock I

CCDC reference: 651710

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.026
wR factor = 0.069
Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         84 PerFi
PLAT420_ALERT_2_B D-H Without Acceptor       O9     -   H92    ...          ?

Alert level C
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...       0.40
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.70
PLAT731_ALERT_1_C Bond    Calc     0.77(4), Rep   0.763(15) ......       2.67 su-Ra
              O7   -H71     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.77(4), Rep   0.764(15) ......       2.67 su-Ra
              O7   -H72     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.76(4), Rep   0.766(15) ......       2.67 su-Ra
              O9   -H91     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.77(4), Rep   0.764(15) ......       2.67 su-Ra
              O7   -H72     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.77(4), Rep   0.763(15) ......       2.67 su-Ra
              O7   -H71     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.76(4), Rep   0.766(15) ......       2.67 su-Ra
              O9   -H91     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.99(4), Rep   1.990(15) ......       2.67 su-Ra
              H81  -O3      1.555   1.455
PLAT736_ALERT_1_C H...A   Calc     2.03(4), Rep   2.029(17) ......       2.35 su-Ra
              H91  -O6      1.555   1.656
PLAT737_ALERT_1_C D...A   Calc    2.990(4), Rep  2.9901(15) ......       2.67 su-Ra
              O7   -O7      1.555   2.465
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.48 Ratio
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.40

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C4 H14 Na2 O9 S4
            Atom count from _chemical_formula_moiety:C4 H26 Na2 O15 S4
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.697
            Tmax scaled      0.697 Tmin scaled      0.347
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           72.22
           From the CIF: _reflns_number_total               2346
           Count of symmetry unique reflns         1383
           Completeness (_total/calc)            169.63%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       963
           Fraction of Friedel pairs measured     0.696
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          8

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

  11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Dimesna, the disulfide readily formed from mesna (Bambagiotti-Alberti et al., 2007) by oxidation (Li et al., 2003), has been shown to protect against cisplatin-induced nephrotoxicity, due to its conversion in the kidneys into the monomeric mesna which, contrary to dimesna, is effective in inactivating urotoxic metabolites from cisplatin chemotherapy (Verschraagen et al., 2004). On the other hand, direct use of mesna as an aid, instead of dimesna, is discouraged by owing to interference with chemotherapy.

Crystals of dimesna were obtained in the form of the trihydrate (I); the contents of the asymmetric unit are shown in Fig. 1. Corresponding bond distances in the two chemically equivalent parts of the anion are in substantial agreement, as they are with values previously found for mesna. The value of the S—S distance, 2.0338 (10) Å, agrees with values recently reported for this bond in similar environments [2.032 (1) Å (Ren & Zhao, 2006); 2.045 (1) Å (Bolte & Sakhaii, 2004)]. The S3 and S4 atoms are in antiperiplanar positions with respect to the connecting ethyl chain, whereas the S1 and S2 atoms in the other part of the anion are in an a-synclinal arrangement. In the crystal structure, the anionic portions of dimesna are arranged in layers parallel to the ab-face, with interposed layers formed by the cations and two of the water molecules (Fig. 2). The third water molecule (O7) occupies channels parallel to a in the anionic layer, forming chains of hydrogen-bonded water molecules which, in addition, are similarly linked to O atoms of sulfonate residues. The closest approach between S atoms of different anions in a layer is 3.845 (1) Å. Both Na⁺ cations are six-coordinated by O atoms, four of these, in both coordination spheres, belonging to different anions, whereas two are common and are provided by the O8 and O9 water molecules. The latter water O atoms, as well as the sulfonate O1 and O5 atoms, bridge between symmetry-related cations, forming chains along a, whereas the O2 and O4 (also coordinating) sulfonate O atoms provide bridges between the chains. The sulfonate O3 and O6 sulfonate atoms, are not engaged in coordination to Na, but accept hydrogen bonds from water molecules.

Related literature top

For related literature, see: Bambagiotti-Alberti et al. (2007); Bolte & Sakhaii (2004); Li et al. (2003); Ren & Zhao (2006); Verschraagen et al. (2004).

Experimental top

Samples of dimesna, in microcrystalline form, were kindly provided by SIMS (SIMS srl, Reggello Firenze, Italy). Crystals suitable for X-ray diffraction were obtained by slow evaporation from water-methanol solutions of (I).

Structure description top

For related literature, see: Bambagiotti-Alberti et al. (2007); Bolte & Sakhaii (2004); Li et al. (2003); Ren & Zhao (2006); Verschraagen et al. (2004).

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. A view of the contents of the asymmetric unit in (I). Displacement ellipsoids are drawn at the 50% probability level. Cordinative bonds to Na⁺ ions are denoted by thin lines and a hydrogen bond by a dashed line.
	Fig. 2. A view of the crystal packing in (I), viewed along the a axis. Thin lines denote cordinative bonds to Na⁺ ions and dashed lines represent hydrogen bonds.

poly[[di-µ-aqua-µ₄-[2,2'-dithiobis(ethanesulfonato)]-disodium(I)] monohydrate] top

Crystal data top

[Na₂(C₄H₈O₆S₄)(H₂O)₂]·H₂O	F(000) = 392
M_r = 380.37	D_x = 1.806 Mg m⁻³
Monoclinic, Pa	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P -2ya	Cell parameters from 2793 reflections
a = 5.7328 (2) Å	θ = 11.1–44.5°
b = 10.9152 (4) Å	µ = 7.22 mm⁻¹
c = 11.2665 (4) Å	T = 150 K
β = 97.106 (4)°	Prism, colourless
V = 699.58 (4) Å³	0.15 × 0.10 × 0.05 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur PX Ultra CCD diffractometer	2346 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
Oxford Diffraction, Enhance ULTRA assembly monochromator	R_int = 0.034
ω scans	θ_max = 72.2°, θ_min = 4.0°
Absorption correction: multi-scan [ABSPACK from CrysAlis PRO RED (Oxford Diffraction, 2006)]	h = −7→5
T_min = 0.498, T_max = 1.000	k = −13→13
8713 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0548P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2346 reflections	Δρ_max = 0.33 e Å⁻³
192 parameters	Δρ_min = −0.40 e Å⁻³
8 restraints	Absolute structure: Flack & Bernardinelli (1999); 977 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (4)

Crystal data top

[Na₂(C₄H₈O₆S₄)(H₂O)₂]·H₂O	V = 699.58 (4) Å³
M_r = 380.37	Z = 2
Monoclinic, Pa	Cu Kα radiation
a = 5.7328 (2) Å	µ = 7.22 mm⁻¹
b = 10.9152 (4) Å	T = 150 K
c = 11.2665 (4) Å	0.15 × 0.10 × 0.05 mm
β = 97.106 (4)°

Data collection top

Oxford Diffraction Xcalibur PX Ultra CCD diffractometer	2346 independent reflections
Absorption correction: multi-scan [ABSPACK from CrysAlis PRO RED (Oxford Diffraction, 2006)]	2246 reflections with I > 2σ(I)
T_min = 0.498, T_max = 1.000	R_int = 0.034
8713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.069	Δρ_max = 0.33 e Å⁻³
S = 1.04	Δρ_min = −0.40 e Å⁻³
2346 reflections	Absolute structure: Flack & Bernardinelli (1999); 977 Friedel pairs
192 parameters	Absolute structure parameter: 0.0 (4)
8 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.44292 (10)	0.31465 (5)	0.07585 (5)	0.01495 (15)
O1	0.5960 (4)	0.41544 (17)	0.12214 (18)	0.0202 (4)
O2	0.2687 (4)	0.28386 (18)	0.15533 (17)	0.0193 (4)
O3	0.5760 (4)	0.20872 (19)	0.04342 (18)	0.0219 (4)
C1	0.2838 (5)	0.3722 (2)	−0.0587 (2)	0.0180 (6)
H11	0.2401	0.4585	−0.0457	0.022*
H12	0.3883	0.3714	−0.1224	0.022*
C2	0.0601 (6)	0.2998 (3)	−0.1022 (3)	0.0228 (6)
H21	−0.0269	0.3449	−0.1700	0.027*
H22	−0.0405	0.2983	−0.0368	0.027*
S2	0.10126 (14)	0.14314 (6)	−0.14969 (7)	0.02739 (18)
S3	0.32883 (13)	0.15983 (7)	−0.27364 (6)	0.02457 (16)
C3	0.1429 (6)	0.2132 (3)	−0.4068 (3)	0.0211 (6)
H31	0.0754	0.2937	−0.3894	0.025*
H32	0.2414	0.2250	−0.4721	0.025*
C4	−0.0557 (5)	0.1259 (2)	−0.4490 (2)	0.0181 (6)
H41	−0.1568	0.1147	−0.3847	0.022*
H42	0.0102	0.0451	−0.4668	0.022*
S4	−0.22768 (11)	0.18324 (5)	−0.57943 (5)	0.01576 (15)
O4	−0.0636 (4)	0.21572 (19)	−0.66323 (17)	0.0189 (4)
O5	−0.3898 (4)	0.08517 (19)	−0.62452 (17)	0.0227 (5)
O6	−0.3523 (4)	0.2900 (2)	−0.53982 (18)	0.0240 (5)
Na1	0.22800 (19)	0.09442 (9)	0.25452 (9)	0.0182 (2)
Na2	−0.02409 (19)	0.40532 (10)	0.23478 (10)	0.0192 (2)
O7	−0.3003 (5)	0.4610 (2)	−0.3525 (3)	0.0491 (7)
H71	−0.423 (5)	0.473 (6)	−0.335 (5)	0.074*
H72	−0.325 (11)	0.398 (3)	−0.381 (5)	0.074*
O8	−0.0935 (4)	0.03360 (18)	0.11922 (19)	0.0198 (4)
H81	−0.184 (6)	0.084 (3)	0.102 (4)	0.030*
H82	−0.074 (7)	−0.014 (3)	0.072 (3)	0.030*
O9	0.3065 (4)	0.45846 (17)	0.3702 (2)	0.0212 (4)
H91	0.391 (6)	0.406 (3)	0.388 (4)	0.032*
H92	0.297 (7)	0.488 (3)	0.431 (2)	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0134 (3)	0.0140 (3)	0.0169 (3)	0.0005 (2)	−0.0004 (2)	0.0005 (2)
O1	0.0185 (11)	0.0191 (10)	0.0218 (10)	−0.0035 (8)	−0.0019 (8)	−0.0010 (8)
O2	0.0186 (11)	0.0204 (9)	0.0192 (10)	0.0000 (8)	0.0040 (9)	0.0006 (8)
O3	0.0204 (11)	0.0197 (9)	0.0256 (11)	0.0053 (9)	0.0032 (9)	−0.0008 (8)
C1	0.0193 (15)	0.0162 (13)	0.0172 (13)	0.0011 (10)	−0.0036 (11)	0.0001 (10)
C2	0.0181 (16)	0.0301 (15)	0.0191 (14)	−0.0019 (12)	−0.0017 (12)	−0.0032 (11)
S2	0.0381 (5)	0.0249 (3)	0.0179 (3)	−0.0104 (3)	−0.0015 (3)	−0.0007 (3)
S3	0.0230 (4)	0.0286 (3)	0.0202 (3)	0.0046 (3)	−0.0052 (3)	−0.0050 (3)
C3	0.0220 (15)	0.0237 (13)	0.0174 (14)	−0.0011 (12)	0.0011 (11)	0.0019 (11)
C4	0.0198 (15)	0.0189 (13)	0.0148 (13)	−0.0006 (11)	−0.0012 (11)	0.0028 (10)
S4	0.0148 (3)	0.0180 (3)	0.0142 (3)	0.0006 (2)	0.0007 (2)	0.0008 (2)
O4	0.0191 (11)	0.0206 (9)	0.0175 (10)	0.0018 (8)	0.0049 (8)	0.0022 (7)
O5	0.0206 (12)	0.0248 (10)	0.0208 (11)	−0.0052 (8)	−0.0045 (9)	0.0018 (7)
O6	0.0243 (12)	0.0270 (10)	0.0205 (10)	0.0105 (9)	0.0015 (9)	−0.0017 (9)
Na1	0.0159 (6)	0.0188 (5)	0.0197 (5)	0.0001 (4)	0.0012 (5)	−0.0005 (4)
Na2	0.0167 (6)	0.0177 (5)	0.0221 (6)	0.0006 (4)	−0.0014 (5)	0.0003 (4)
O7	0.0488 (17)	0.0285 (13)	0.0649 (19)	−0.0014 (12)	−0.0139 (15)	−0.0125 (12)
O8	0.0162 (10)	0.0190 (10)	0.0233 (10)	0.0021 (8)	−0.0020 (8)	0.0002 (7)
O9	0.0180 (10)	0.0216 (10)	0.0233 (10)	0.0029 (8)	0.0000 (8)	−0.0028 (8)

Geometric parameters (Å, º) top

S1—O3	1.457 (2)	O4—Na1ⁱⁱⁱ	2.406 (2)
S1—O2	1.461 (2)	O5—Na1^iv	2.435 (2)
S1—O1	1.4626 (19)	O5—Na1^v	2.527 (2)
S1—C1	1.784 (3)	Na1—O8	2.338 (2)
O1—Na2ⁱ	2.384 (2)	Na1—O8^vi	2.389 (2)
O1—Na2ⁱⁱ	2.476 (2)	Na1—O4^vii	2.406 (2)
O2—Na1	2.376 (2)	Na1—O5^viii	2.435 (2)
O2—Na2	2.397 (2)	Na1—O5^ix	2.527 (2)
C1—C2	1.534 (4)	Na1—Na1^x	3.5305 (12)
C1—H11	0.9900	Na1—Na1^vi	3.5305 (12)
C1—H12	0.9900	Na2—O9	2.354 (2)
C2—S2	1.816 (3)	Na2—O1^xi	2.384 (2)
C2—H21	0.9900	Na2—O4^vii	2.392 (2)
C2—H22	0.9900	Na2—O9^xii	2.419 (2)
S2—S3	2.0338 (10)	Na2—O1^xii	2.476 (2)
S3—C3	1.825 (3)	Na2—Na2ⁱⁱ	3.5339 (12)
C3—C4	1.515 (4)	Na2—Na2^xii	3.5339 (12)
C3—H31	0.9900	O7—H71	0.763 (15)
C3—H32	0.9900	O7—H72	0.764 (15)
C4—S4	1.779 (3)	O8—Na1^x	2.389 (2)
C4—H41	0.9900	O8—H81	0.763 (15)
C4—H42	0.9900	O8—H82	0.764 (15)
S4—O4	1.456 (2)	O9—Na2ⁱⁱ	2.419 (2)
S4—O6	1.465 (2)	O9—H91	0.766 (15)
S4—O5	1.467 (2)	O9—H92	0.763 (15)
O4—Na2ⁱⁱⁱ	2.392 (2)

O3—S1—O2	112.97 (12)	O8—Na1—O5^ix	83.66 (7)
O3—S1—O1	112.14 (12)	O2—Na1—O5^ix	167.79 (8)
O2—S1—O1	112.34 (12)	O8^vi—Na1—O5^ix	93.13 (8)
O3—S1—C1	107.16 (12)	O4^vii—Na1—O5^ix	88.53 (7)
O2—S1—C1	106.57 (13)	O5^viii—Na1—O5^ix	87.02 (7)
O1—S1—C1	105.04 (12)	O8—Na1—Na1^x	42.24 (6)
S1—O1—Na2ⁱ	128.56 (12)	O2—Na1—Na1^x	129.43 (6)
S1—O1—Na2ⁱⁱ	125.78 (12)	O8^vi—Na1—Na1^x	94.03 (6)
Na2ⁱ—O1—Na2ⁱⁱ	93.29 (7)	O4^vii—Na1—Na1^x	73.65 (5)
S1—O2—Na1	127.08 (12)	O5^viii—Na1—Na1^x	130.55 (6)
S1—O2—Na2	131.69 (12)	O5^ix—Na1—Na1^x	43.60 (5)
Na1—O2—Na2	101.06 (8)	O8—Na1—Na1^vi	114.13 (7)
C2—C1—S1	114.2 (2)	O2—Na1—Na1^vi	112.41 (6)
C2—C1—H11	108.7	O8^vi—Na1—Na1^vi	41.13 (6)
S1—C1—H11	108.7	O4^vii—Na1—Na1^vi	157.52 (5)
C2—C1—H12	108.7	O5^viii—Na1—Na1^vi	45.69 (5)
S1—C1—H12	108.7	O5^ix—Na1—Na1^vi	79.53 (6)
H11—C1—H12	107.6	Na1^x—Na1—Na1^vi	108.56 (5)
C1—C2—S2	116.4 (2)	O9—Na2—O1^xi	160.56 (8)
C1—C2—H21	108.2	O9—Na2—O4^vii	91.05 (8)
S2—C2—H21	108.2	O1^xi—Na2—O4^vii	99.28 (8)
C1—C2—H22	108.2	O9—Na2—O2	80.42 (8)
S2—C2—H22	108.2	O1^xi—Na2—O2	117.56 (8)
H21—C2—H22	107.3	O4^vii—Na2—O2	79.24 (7)
C2—S2—S3	103.64 (11)	O9—Na2—O9^xii	78.08 (7)
C3—S3—S2	103.52 (11)	O1^xi—Na2—O9^xii	84.01 (8)
C4—C3—S3	113.44 (19)	O4^vii—Na2—O9^xii	99.18 (8)
C4—C3—H31	108.9	O2—Na2—O9^xii	158.42 (9)
S3—C3—H31	108.9	O9—Na2—O1^xii	83.39 (8)
C4—C3—H32	108.9	O1^xi—Na2—O1^xii	89.09 (7)
S3—C3—H32	108.9	O4^vii—Na2—O1^xii	168.28 (9)
H31—C3—H32	107.7	O2—Na2—O1^xii	89.64 (7)
C3—C4—S4	110.91 (18)	O9^xii—Na2—O1^xii	89.79 (7)
C3—C4—H41	109.5	O9—Na2—Na2ⁱⁱ	42.94 (6)
S4—C4—H41	109.5	O1^xi—Na2—Na2ⁱⁱ	131.34 (6)
C3—C4—H42	109.5	O4^vii—Na2—Na2ⁱⁱ	129.14 (6)
S4—C4—H42	109.5	O2—Na2—Na2ⁱⁱ	73.63 (5)
H41—C4—H42	108.0	O9^xii—Na2—Na2ⁱⁱ	91.69 (6)
O4—S4—O6	112.47 (13)	O1^xii—Na2—Na2ⁱⁱ	42.33 (5)
O4—S4—O5	112.68 (12)	O9—Na2—Na2^xii	116.35 (6)
O6—S4—O5	111.96 (13)	O1^xi—Na2—Na2^xii	44.37 (5)
O4—S4—C4	106.54 (13)	O4^vii—Na2—Na2^xii	112.40 (6)
O6—S4—C4	105.63 (13)	O2—Na2—Na2^xii	158.24 (5)
O5—S4—C4	106.99 (12)	O9^xii—Na2—Na2^xii	41.53 (6)
S4—O4—Na2ⁱⁱⁱ	129.00 (12)	O1^xii—Na2—Na2^xii	79.32 (6)
S4—O4—Na1ⁱⁱⁱ	130.60 (12)	Na2ⁱⁱ—Na2—Na2^xii	108.41 (6)
Na2ⁱⁱⁱ—O4—Na1ⁱⁱⁱ	100.33 (8)	H71—O7—H72	97 (6)
S4—O5—Na1^iv	130.65 (12)	Na1—O8—Na1^x	96.63 (9)
S4—O5—Na1^v	123.57 (13)	Na1—O8—H81	115 (3)
Na1^iv—O5—Na1^v	90.70 (7)	Na1^x—O8—H81	104 (3)
O8—Na1—O2	93.20 (8)	Na1—O8—H82	119 (3)
O8—Na1—O8^vi	77.48 (7)	Na1^x—O8—H82	99 (3)
O2—Na1—O8^vi	97.72 (8)	H81—O8—H82	118 (4)
O8—Na1—O4^vii	82.99 (8)	Na2—O9—Na2ⁱⁱ	95.53 (9)
O2—Na1—O4^vii	79.37 (7)	Na2—O9—H91	115 (3)
O8^vi—Na1—O4^vii	160.09 (8)	Na2ⁱⁱ—O9—H91	110 (3)
O8—Na1—O5^viii	159.28 (9)	Na2—O9—H92	123 (3)
O2—Na1—O5^viii	99.53 (8)	Na2ⁱⁱ—O9—H92	113 (3)
O8^vi—Na1—O5^viii	84.62 (8)	H91—O9—H92	101 (4)
O4^vii—Na1—O5^viii	115.29 (8)

O3—S1—O1—Na2ⁱ	−32.55 (19)	Na2—O2—Na1—O8^vi	159.45 (8)
O2—S1—O1—Na2ⁱ	95.97 (16)	S1—O2—Na1—O4^vii	175.00 (14)
C1—S1—O1—Na2ⁱ	−148.59 (15)	Na2—O2—Na1—O4^vii	−0.59 (9)
O3—S1—O1—Na2ⁱⁱ	−164.23 (12)	S1—O2—Na1—O5^viii	60.84 (16)
O2—S1—O1—Na2ⁱⁱ	−35.72 (17)	Na2—O2—Na1—O5^viii	−114.75 (8)
C1—S1—O1—Na2ⁱⁱ	79.73 (16)	S1—O2—Na1—O5^ix	−177.4 (3)
O3—S1—O2—Na1	9.99 (19)	Na2—O2—Na1—O5^ix	7.0 (4)
O1—S1—O2—Na1	−118.08 (14)	S1—O2—Na1—Na1^x	−126.68 (13)
C1—S1—O2—Na1	127.41 (14)	Na2—O2—Na1—Na1^x	57.72 (10)
O3—S1—O2—Na2	−175.80 (14)	S1—O2—Na1—Na1^vi	15.03 (16)
O1—S1—O2—Na2	56.13 (19)	Na2—O2—Na1—Na1^vi	−160.57 (5)
C1—S1—O2—Na2	−58.39 (18)	S1—O2—Na2—O9	−81.77 (16)
O3—S1—C1—C2	79.0 (2)	Na1—O2—Na2—O9	93.52 (9)
O2—S1—C1—C2	−42.2 (2)	S1—O2—Na2—O1^xi	90.38 (17)
O1—S1—C1—C2	−161.6 (2)	Na1—O2—Na2—O1^xi	−94.33 (9)
S1—C1—C2—S2	−65.8 (3)	S1—O2—Na2—O4^vii	−174.69 (15)
C1—C2—S2—S3	−53.8 (2)	Na1—O2—Na2—O4^vii	0.60 (9)
C2—S2—S3—C3	−77.94 (14)	S1—O2—Na2—O9^xii	−86.9 (3)
S2—S3—C3—C4	−59.4 (2)	Na1—O2—Na2—O9^xii	88.3 (2)
S3—C3—C4—S4	−179.55 (16)	S1—O2—Na2—O1^xii	1.59 (17)
C3—C4—S4—O4	50.4 (2)	Na1—O2—Na2—O1^xii	176.88 (8)
C3—C4—S4—O6	−69.4 (2)	S1—O2—Na2—Na2ⁱⁱ	−38.18 (14)
C3—C4—S4—O5	171.12 (19)	Na1—O2—Na2—Na2ⁱⁱ	137.11 (8)
O6—S4—O4—Na2ⁱⁱⁱ	−11.5 (2)	S1—O2—Na2—Na2^xii	60.6 (3)
O5—S4—O4—Na2ⁱⁱⁱ	116.17 (15)	Na1—O2—Na2—Na2^xii	−124.15 (16)
C4—S4—O4—Na2ⁱⁱⁱ	−126.80 (15)	O2—Na1—O8—Na1^x	−152.21 (8)
O6—S4—O4—Na1ⁱⁱⁱ	171.83 (14)	O8^vi—Na1—O8—Na1^x	110.59 (12)
O5—S4—O4—Na1ⁱⁱⁱ	−60.48 (19)	O4^vii—Na1—O8—Na1^x	−73.34 (7)
C4—S4—O4—Na1ⁱⁱⁱ	56.55 (18)	O5^viii—Na1—O8—Na1^x	79.7 (3)
O4—S4—O5—Na1^iv	−88.73 (18)	O5^ix—Na1—O8—Na1^x	15.95 (8)
O6—S4—O5—Na1^iv	39.24 (19)	Na1^vi—Na1—O8—Na1^x	91.46 (8)
C4—S4—O5—Na1^iv	154.52 (15)	O1^xi—Na2—O9—Na2ⁱⁱ	−82.5 (3)
O4—S4—O5—Na1^v	37.37 (16)	O4^vii—Na2—O9—Na2ⁱⁱ	155.11 (8)
O6—S4—O5—Na1^v	165.33 (12)	O2—Na2—O9—Na2ⁱⁱ	76.21 (7)
C4—S4—O5—Na1^v	−79.39 (16)	O9^xii—Na2—O9—Na2ⁱⁱ	−105.73 (11)
S1—O2—Na1—O8	−102.75 (15)	O1^xii—Na2—O9—Na2ⁱⁱ	−14.54 (7)
Na2—O2—Na1—O8	81.66 (9)	Na2^xii—Na2—O9—Na2ⁱⁱ	−89.14 (8)
S1—O2—Na1—O8^vi	−24.95 (16)

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1, z; (iii) x, y, z−1; (iv) x−1, y, z−1; (v) x−1/2, −y, z−1; (vi) x+1/2, −y, z; (vii) x, y, z+1; (viii) x+1, y, z+1; (ix) x+1/2, −y, z+1; (x) x−1/2, −y, z; (xi) x−1, y, z; (xii) x−1/2, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H72···O6	0.76 (2)	2.14 (3)	2.806 (3)	147 (6)
O7—H71···O7^xii	0.76 (2)	2.27 (3)	2.9901 (15)	158 (6)
O8—H81···O3^xi	0.76 (2)	1.99 (2)	2.752 (3)	175 (4)
O8—H82···O3^x	0.76 (2)	2.33 (3)	2.979 (3)	144 (4)
O9—H91···O6^viii	0.77 (2)	2.03 (2)	2.783 (3)	168 (4)

Symmetry codes: (viii) x+1, y, z+1; (x) x−1/2, −y, z; (xi) x−1, y, z; (xii) x−1/2, −y+1, z.

Experimental details

Crystal data
Chemical formula	[Na₂(C₄H₈O₆S₄)(H₂O)₂]·H₂O
M_r	380.37
Crystal system, space group	Monoclinic, Pa
Temperature (K)	150
a, b, c (Å)	5.7328 (2), 10.9152 (4), 11.2665 (4)
β (°)	97.106 (4)
V (Å³)	699.58 (4)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	7.22
Crystal size (mm)	0.15 × 0.10 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur PX Ultra CCD
Absorption correction	Multi-scan [ABSPACK from CrysAlis PRO RED (Oxford Diffraction, 2006)]
T_min, T_max	0.498, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8713, 2346, 2246
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.069, 1.04
No. of reflections	2346
No. of parameters	192
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.40
Absolute structure	Flack & Bernardinelli (1999); 977 Friedel pairs
Absolute structure parameter	0.0 (4)

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2006), CrysAlis PRO CCD, CrysAlis PRO RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H72···O6	0.764 (15)	2.14 (3)	2.806 (3)	147 (6)
O7—H71···O7ⁱ	0.763 (15)	2.27 (3)	2.9901 (15)	158 (6)
O8—H81···O3ⁱⁱ	0.763 (15)	1.990 (15)	2.752 (3)	175 (4)
O8—H82···O3ⁱⁱⁱ	0.764 (15)	2.33 (3)	2.979 (3)	144 (4)
O9—H91···O6^iv	0.766 (15)	2.029 (17)	2.783 (3)	168 (4)

Symmetry codes: (i) x−1/2, −y+1, z; (ii) x−1, y, z; (iii) x−1/2, −y, z; (iv) x+1, y, z+1.

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