Dilithium 1,2,5-thia­diazo­lidine-3,4-dione 1,1-dioxide dihydrate

McOwen, D.W.; Delp, S.A.; Boyle, P.D.; Henderson, W.A.

doi:10.1107/S1600536812036379

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page m1228

doi:10.1107/S1600536812036379

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Dilithium 1,2,5-thiadiazolidine-3,4-dione 1,1-dioxide dihydrate

Dennis W. McOwen,^a Samuel A. Delp,^a Paul D. Boyle ^b and Wesley A. Henderson ^a ^*

^aIonic Liquids and Electrolytes for Energy Technologies (ILEET) Laboratory, Department of Chemical and Biomolecular Engineering, North Carolina State University, 911 Partners Way, Raleigh, NC 27695, USA, and ^bX-ray Structural Facility, Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, NC 27695, USA
^*Correspondence e-mail: whender@ncsu.edu

(Received 10 August 2012; accepted 20 August 2012; online 31 August 2012)

The title compound, poly[μ-aqua-aqua-μ₆-(1,1-dioxo-1λ⁶,2,5-thiadiazolidine-3,4-diolato)-dilithium], [Li₂(C₂N₂O₄S)(H₂O)₂]_n or (H₂O)₂:Li₂TDD, forms an infinite three-dimensional structure containing five-coordinate (Li/5) and six-coordinate (Li/6) Li⁺ cations. Li/5 is coordinated by three water molecules, one carbonyl O atom and one sulfuryl O atom while Li/6 is coordinated by one water molecule, three carbonyl O atoms, and two sulfuryl O atoms. Each water molecule bridges two Li⁺ cations, while also hydrogen bonding to either one endocyclic N atom and one sulfuryl O atom or two endocyclic N atoms. While the endocyclic N atoms in the anion do not coordinate the Li⁺ cations, the carbonyl and sulfuryl groups each coordinate three Li⁺ cations, which gives rise to the infinite three-dimensional structure.

Related literature

For Na salt synthesis, see: Lee & Kohn (1990 ). For Na salt, K salt, and acid form synthesis, see: Wen et al. (1975 ).

Experimental

Crystal data

[Li₂(C₂N₂O₄S)(H₂O)₂]
M_r = 198.01
Monoclinic, P 2₁ /c
a = 7.239 (3) Å
b = 11.185 (3) Å
c = 9.786 (4) Å
β = 124.27 (2)°
V = 654.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 110 K
0.41 × 0.24 × 0.24 mm

Data collection

Bruker–Nonius Kappa X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.825, T_max = 0.894
34710 measured reflections
3899 independent reflections
3575 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.065
S = 1.06
3899 reflections
134 parameters
All H-atom parameters refined
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯N2ⁱ	0.791 (16)	2.155 (16)	2.9428 (14)	175 (2)
O1W—H1WB⋯O1ⁱⁱ	0.842 (17)	2.29 (2)	2.9971 (15)	142 (2)
O2W—H2WA⋯N2ⁱⁱⁱ	0.823 (16)	2.049 (16)	2.8712 (14)	175.7 (16)
O2W—H2WB⋯N1^iv	0.79 (2)	2.01 (2)	2.7947 (14)	168.7 (17)
Symmetry codes: (i) -x+2, -y, -z+2; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036379/qm2080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036379/qm2080Isup2.hkl

checkCIF report

Comment top

Dilithium 1,2,5-thiadiazolidine-3,4-dione 1,1-dioxide (Li₂TDD) was synthesized following methods reported in the literature for the anion (Lee et al., Wen et al.). The salt forms a dihydrate in which the carbonyl and sulfuryl oxygen atoms each coordinate multiple Li⁺ cations forming a highly aggregated structure. In addition, each water molecule bridges two Li⁺ cations. The endocyclic nitrogen atoms, however, are not coordinated to the Li⁺ cations, indicating that the O atoms atoms exhibit the greatest Lewis basicity.

Related literature top

For Na salt synthesis, see: Lee et al. (1990). For Na salt, K salt, and acid form synthesis procedures, see: Wen et al. (1975).

Experimental top

Sulfamide (1.00 eq.) was dissolved in methanol and slowly added to a solution of LiMeO (2.10 eq.) at room temperature, resulting in a cloudy white solution. After addition of diethyl oxalate (1.05 eq.), the solution became clear. After gently refluxing for 20 h, the solvent was removed under vacuum and a clear viscous solution was obtained. Upon addition of deionized water, crystals suitable for characterization formed.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Asymmetric unit of the Li₂TDD dihydrate crystal structure. Thermal ellipsoids are at 50% probability (Li-purple, O-red, S-yellow, N-blue).
	Fig. 2. Packing diagram for the Li₂TDD dihydrate crystal structure (Li-purple, O-red, S-yellow, N-blue).

Poly[µ-aqua-aqua-µ₆-(1,1-dioxo-1λ⁶,2,5-thiadiazolidine-3,4-diolato)- dilithium] top

Crystal data top

[Li₂(C₂N₂O₄S)(H₂O₂)]	F(000) = 400
M_r = 198.01	D_x = 2.008 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.239 (3) Å	Cell parameters from 9851 reflections
b = 11.185 (3) Å	θ = 3.1–42.4°
c = 9.786 (4) Å	µ = 0.49 mm⁻¹
β = 124.27 (2)°	T = 110 K
V = 654.8 (4) Å³	Prism, colourless
Z = 4	0.41 × 0.24 × 0.24 mm

Data collection top

Bruker–Nonius Kappa X8 APEXII diffractometer	3899 independent reflections
Radiation source: fine-focus sealed tube	3575 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω and ϕ scans	θ_max = 42.7°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
T_min = 0.825, T_max = 0.894	k = −18→19
34710 measured reflections	l = −16→18

Refinement top

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0343P)² + 0.1822P] where P = (F_o² + 2F_c²)/3
3899 reflections	(Δ/σ)_max = 0.001
134 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Li₂(C₂N₂O₄S)(H₂O₂)]	V = 654.8 (4) Å³
M_r = 198.01	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.239 (3) Å	µ = 0.49 mm⁻¹
b = 11.185 (3) Å	T = 110 K
c = 9.786 (4) Å	0.41 × 0.24 × 0.24 mm
β = 124.27 (2)°

Data collection top

Bruker–Nonius Kappa X8 APEXII diffractometer	3899 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3575 reflections with I > 2σ(I)
T_min = 0.825, T_max = 0.894	R_int = 0.022
34710 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.065	All H-atom parameters refined
S = 1.06	Δρ_max = 0.62 e Å⁻³
3899 reflections	Δρ_min = −0.40 e Å⁻³
134 parameters

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
Li1	0.7137 (2)	0.01566 (12)	0.50356 (15)	0.0135 (2)
Li2	0.7135 (2)	0.05125 (12)	0.18236 (17)	0.0149 (2)
S1	0.89112 (2)	0.223295 (11)	0.983764 (16)	0.00633 (4)
O1	0.79819 (8)	0.19195 (4)	1.07658 (6)	0.01045 (7)
O2	0.84435 (8)	0.34610 (4)	0.92528 (6)	0.01025 (7)
N1	0.79993 (8)	0.13338 (4)	0.82836 (6)	0.00815 (8)
N2	1.16044 (8)	0.19981 (5)	1.09118 (6)	0.00814 (7)
C1	0.97800 (9)	0.08981 (5)	0.83782 (7)	0.00681 (8)
C2	1.19895 (9)	0.12853 (5)	0.99882 (7)	0.00704 (8)
O3	0.97919 (7)	0.02518 (4)	0.73492 (5)	0.00883 (7)
O4	1.38036 (7)	0.09387 (4)	1.02912 (6)	0.01080 (8)
O1W	0.56092 (8)	−0.12147 (4)	0.56167 (6)	0.01060 (7)
H1WA	0.642 (3)	−0.1436 (15)	0.654 (2)	0.038 (4)*
H1WB	0.497 (3)	−0.1828 (15)	0.504 (2)	0.037 (4)*
O2W	0.64205 (7)	−0.06718 (4)	0.30255 (6)	0.00860 (7)
H2WA	0.702 (2)	−0.1334 (14)	0.3304 (18)	0.030 (3)*
H2WB	0.512 (3)	−0.0804 (14)	0.2543 (19)	0.032 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Li1	0.0127 (5)	0.0155 (5)	0.0110 (5)	−0.0009 (4)	0.0059 (4)	−0.0018 (4)
Li2	0.0120 (5)	0.0169 (5)	0.0176 (5)	0.0033 (4)	0.0094 (5)	0.0054 (4)
S1	0.00648 (6)	0.00602 (6)	0.00737 (6)	0.00044 (3)	0.00444 (5)	−0.00002 (3)
O1	0.01270 (18)	0.01092 (17)	0.01269 (18)	0.00098 (14)	0.01016 (16)	0.00139 (13)
O2	0.01357 (18)	0.00648 (15)	0.01303 (18)	0.00244 (13)	0.00890 (16)	0.00195 (13)
N1	0.00613 (17)	0.00947 (17)	0.00851 (17)	−0.00019 (13)	0.00391 (15)	−0.00189 (14)
N2	0.00659 (17)	0.00924 (17)	0.00772 (17)	−0.00007 (14)	0.00350 (15)	−0.00125 (14)
C1	0.00696 (19)	0.00660 (18)	0.00715 (18)	0.00008 (14)	0.00413 (16)	0.00011 (14)
C2	0.00620 (18)	0.00760 (18)	0.00714 (18)	0.00043 (14)	0.00365 (16)	0.00069 (14)
O3	0.00976 (17)	0.00902 (16)	0.00814 (16)	0.00060 (13)	0.00530 (14)	−0.00166 (12)
O4	0.00685 (16)	0.01436 (18)	0.01147 (17)	0.00300 (13)	0.00532 (15)	0.00209 (14)
O1W	0.01054 (17)	0.01104 (17)	0.00911 (17)	−0.00189 (13)	0.00487 (15)	−0.00023 (13)
O2W	0.00740 (16)	0.00840 (15)	0.00953 (16)	0.00014 (12)	0.00449 (14)	0.00025 (12)

Geometric parameters (Å, º) top

Li1—O2W	1.9615 (15)	S1—N2	1.6331 (9)
Li1—O3	1.9825 (16)	O1—Li2^vii	2.1539 (14)
Li1—O1Wⁱ	2.0814 (16)	O2—Li1^viii	2.1650 (14)
Li1—O1W	2.1468 (15)	O2—Li2^viii	2.3088 (17)
Li1—O2ⁱⁱ	2.1650 (14)	N1—C1	1.3317 (9)
Li1—Li1ⁱ	3.076 (3)	N2—C2	1.3469 (8)
Li1—Li2	3.167 (2)	C1—O3	1.2435 (7)
Li1—H2WB	2.286 (16)	C1—C2	1.5460 (10)
Li2—O2W	2.0226 (14)	C2—O4	1.2346 (8)
Li2—O4ⁱⁱⁱ	2.0539 (17)	O3—Li2^iv	2.0755 (16)
Li2—O3^iv	2.0755 (16)	O4—Li2^ix	2.0539 (17)
Li2—O1^v	2.1539 (14)	O4—Li2^iv	2.4075 (17)
Li2—O2ⁱⁱ	2.3088 (17)	O1W—Li1ⁱ	2.0814 (16)
Li2—O4^iv	2.4075 (17)	O1W—H1WA	0.792 (17)
Li2—Li2^vi	3.344 (3)	O1W—H1WB	0.840 (17)
S1—O1	1.4453 (6)	O2W—H2WA	0.824 (16)
S1—O2	1.4529 (6)	O2W—H2WB	0.794 (16)
S1—N1	1.6216 (7)

O2W—Li1—O3	135.20 (8)	O1^v—Li2—Li1	136.68 (7)
O2W—Li1—O1Wⁱ	107.07 (7)	O2ⁱⁱ—Li2—Li1	43.12 (4)
O3—Li1—O1Wⁱ	117.64 (7)	O4^iv—Li2—Li1	127.63 (6)
O2W—Li1—O1W	92.49 (6)	O2W—Li2—Li2^vi	90.62 (7)
O3—Li1—O1W	92.78 (6)	O4ⁱⁱⁱ—Li2—Li2^vi	45.64 (4)
O1Wⁱ—Li1—O1W	86.66 (6)	O3^iv—Li2—Li2^vi	114.74 (8)
O2W—Li1—O2ⁱⁱ	84.50 (6)	O1^v—Li2—Li2^vi	94.57 (7)
O3—Li1—O2ⁱⁱ	91.73 (6)	O2ⁱⁱ—Li2—Li2^vi	150.02 (7)
O1Wⁱ—Li1—O2ⁱⁱ	91.01 (6)	O4^iv—Li2—Li2^vi	37.58 (4)
O1W—Li1—O2ⁱⁱ	175.48 (7)	Li1—Li2—Li2^vi	119.99 (7)
O2W—Li1—Li1ⁱ	103.23 (7)	O1—S1—O2	112.91 (3)
O3—Li1—Li1ⁱ	110.35 (8)	O1—S1—N1	110.57 (4)
O1Wⁱ—Li1—Li1ⁱ	44.16 (4)	O2—S1—N1	109.60 (4)
O1W—Li1—Li1ⁱ	42.49 (4)	O1—S1—N2	111.47 (4)
O2ⁱⁱ—Li1—Li1ⁱ	135.04 (8)	O2—S1—N2	109.54 (3)
O2W—Li1—Li2	38.02 (4)	N1—S1—N2	102.23 (3)
O3—Li1—Li2	125.81 (7)	S1—O1—Li2^vii	146.99 (5)
O1Wⁱ—Li1—Li2	99.07 (6)	S1—O2—Li1^viii	125.95 (5)
O1W—Li1—Li2	129.81 (6)	S1—O2—Li2^viii	138.18 (4)
O2ⁱⁱ—Li1—Li2	46.80 (4)	Li1^viii—O2—Li2^viii	90.08 (5)
Li1ⁱ—Li1—Li2	123.61 (7)	C1—N1—S1	107.15 (5)
O2W—Li1—H2WB	19.7 (4)	C2—N2—S1	106.65 (5)
O3—Li1—H2WB	150.4 (4)	O3—C1—N1	127.18 (6)
O1Wⁱ—Li1—H2WB	90.8 (4)	O3—C1—C2	120.88 (5)
O1W—Li1—H2WB	80.3 (4)	N1—C1—C2	111.95 (5)
O2ⁱⁱ—Li1—H2WB	95.9 (4)	O4—C2—N2	128.23 (6)
Li1ⁱ—Li1—H2WB	83.8 (4)	O4—C2—C1	120.46 (6)
Li2—Li1—H2WB	50.0 (4)	N2—C2—C1	111.31 (5)
O2W—Li2—O4ⁱⁱⁱ	89.83 (6)	C1—O3—Li1	120.78 (6)
O2W—Li2—O3^iv	94.15 (6)	C1—O3—Li2^iv	114.73 (6)
O4ⁱⁱⁱ—Li2—O3^iv	160.11 (8)	Li1—O3—Li2^iv	124.06 (6)
O2W—Li2—O1^v	173.35 (8)	C2—O4—Li2^ix	154.29 (6)
O4ⁱⁱⁱ—Li2—O1^v	90.83 (6)	C2—O4—Li2^iv	104.96 (5)
O3^iv—Li2—O1^v	87.46 (5)	Li2^ix—O4—Li2^iv	96.78 (6)
O2W—Li2—O2ⁱⁱ	79.51 (6)	Li1ⁱ—O1W—Li1	93.34 (6)
O4ⁱⁱⁱ—Li2—O2ⁱⁱ	105.58 (6)	Li1ⁱ—O1W—H1WA	119.4 (12)
O3^iv—Li2—O2ⁱⁱ	94.31 (6)	Li1—O1W—H1WA	111.6 (12)
O1^v—Li2—O2ⁱⁱ	93.94 (6)	Li1ⁱ—O1W—H1WB	100.8 (11)
O2W—Li2—O4^iv	91.01 (6)	Li1—O1W—H1WB	125.3 (11)
O4ⁱⁱⁱ—Li2—O4^iv	83.22 (6)	H1WA—O1W—H1WB	106.4 (16)
O3^iv—Li2—O4^iv	77.24 (5)	Li1—O2W—Li2	105.30 (7)
O1^v—Li2—O4^iv	95.64 (6)	Li1—O2W—H2WA	107.5 (10)
O2ⁱⁱ—Li2—O4^iv	166.89 (6)	Li2—O2W—H2WA	121.4 (10)
O2W—Li2—Li1	36.68 (4)	Li1—O2W—H2WB	103.9 (11)
O4ⁱⁱⁱ—Li2—Li1	95.63 (6)	Li2—O2W—H2WB	112.5 (11)
O3^iv—Li2—Li1	99.19 (6)	H2WA—O2W—H2WB	104.9 (15)

O3—Li1—Li2—O2W	119.85 (9)	O2—S1—N1—C1	107.86 (4)
O1Wⁱ—Li1—Li2—O2W	−106.16 (7)	N2—S1—N1—C1	−8.27 (4)
O1W—Li1—Li2—O2W	−12.94 (6)	O1—S1—N2—C2	125.58 (5)
O2ⁱⁱ—Li1—Li2—O2W	171.05 (8)	O2—S1—N2—C2	−108.72 (5)
Li1ⁱ—Li1—Li2—O2W	−66.17 (8)	N1—S1—N2—C2	7.45 (4)
O2W—Li1—Li2—O4ⁱⁱⁱ	82.11 (7)	S1—N1—C1—O3	−173.88 (5)
O3—Li1—Li2—O4ⁱⁱⁱ	−158.04 (7)	S1—N1—C1—C2	6.29 (5)
O1Wⁱ—Li1—Li2—O4ⁱⁱⁱ	−24.05 (6)	S1—N2—C2—O4	175.91 (5)
O1W—Li1—Li2—O4ⁱⁱⁱ	69.17 (9)	S1—N2—C2—C1	−4.32 (5)
O2ⁱⁱ—Li1—Li2—O4ⁱⁱⁱ	−106.84 (7)	O3—C1—C2—O4	−1.36 (8)
Li1ⁱ—Li1—Li2—O4ⁱⁱⁱ	15.94 (10)	N1—C1—C2—O4	178.47 (5)
O2W—Li1—Li2—O3^iv	−84.58 (7)	O3—C1—C2—N2	178.85 (5)
O3—Li1—Li2—O3^iv	35.28 (9)	N1—C1—C2—N2	−1.32 (6)
O1Wⁱ—Li1—Li2—O3^iv	169.26 (6)	N1—C1—O3—Li1	19.12 (9)
O1W—Li1—Li2—O3^iv	−97.52 (9)	C2—C1—O3—Li1	−161.08 (6)
O2ⁱⁱ—Li1—Li2—O3^iv	86.47 (6)	N1—C1—O3—Li2^iv	−168.10 (6)
Li1ⁱ—Li1—Li2—O3^iv	−150.75 (8)	C2—C1—O3—Li2^iv	11.71 (7)
O2W—Li1—Li2—O1^v	179.33 (11)	O2W—Li1—O3—C1	177.90 (8)
O3—Li1—Li2—O1^v	−60.82 (12)	O1Wⁱ—Li1—O3—C1	1.93 (10)
O1Wⁱ—Li1—Li2—O1^v	73.17 (10)	O1W—Li1—O3—C1	−85.75 (7)
O1W—Li1—Li2—O1^v	166.39 (7)	O2ⁱⁱ—Li1—O3—C1	93.97 (6)
O2ⁱⁱ—Li1—Li2—O1^v	−9.62 (8)	Li1ⁱ—Li1—O3—C1	−46.05 (10)
Li1ⁱ—Li1—Li2—O1^v	113.16 (10)	Li2—Li1—O3—C1	128.60 (7)
O2W—Li1—Li2—O2ⁱⁱ	−171.05 (8)	O2W—Li1—O3—Li2^iv	5.82 (13)
O3—Li1—Li2—O2ⁱⁱ	−51.20 (7)	O1Wⁱ—Li1—O3—Li2^iv	−170.16 (6)
O1Wⁱ—Li1—Li2—O2ⁱⁱ	82.79 (6)	O1W—Li1—O3—Li2^iv	102.16 (7)
O1W—Li1—Li2—O2ⁱⁱ	176.01 (9)	O2ⁱⁱ—Li1—O3—Li2^iv	−78.11 (7)
Li1ⁱ—Li1—Li2—O2ⁱⁱ	122.78 (10)	Li1ⁱ—Li1—O3—Li2^iv	141.87 (7)
O2W—Li1—Li2—O4^iv	−3.65 (6)	Li2—Li1—O3—Li2^iv	−43.48 (11)
O3—Li1—Li2—O4^iv	116.20 (8)	N2—C2—O4—Li2^ix	25.13 (16)
O1Wⁱ—Li1—Li2—O4^iv	−109.82 (7)	C1—C2—O4—Li2^ix	−154.62 (11)
O1W—Li1—Li2—O4^iv	−16.60 (11)	N2—C2—O4—Li2^iv	171.92 (6)
O2ⁱⁱ—Li1—Li2—O4^iv	167.39 (8)	C1—C2—O4—Li2^iv	−7.83 (7)
Li1ⁱ—Li1—Li2—O4^iv	−69.83 (10)	O2W—Li1—O1W—Li1ⁱ	−106.96 (7)
O2W—Li1—Li2—Li2^vi	41.08 (7)	O3—Li1—O1W—Li1ⁱ	117.54 (7)
O3—Li1—Li2—Li2^vi	160.93 (7)	O1Wⁱ—Li1—O1W—Li1ⁱ	0.0
O1Wⁱ—Li1—Li2—Li2^vi	−65.09 (9)	O2ⁱⁱ—Li1—O1W—Li1ⁱ	−58.9 (9)
O1W—Li1—Li2—Li2^vi	28.13 (11)	Li2—Li1—O1W—Li1ⁱ	−99.03 (8)
O2ⁱⁱ—Li1—Li2—Li2^vi	−147.88 (9)	O3—Li1—O2W—Li2	−93.45 (11)
Li1ⁱ—Li1—Li2—Li2^vi	−25.09 (12)	O1Wⁱ—Li1—O2W—Li2	82.82 (7)
O2—S1—O1—Li2^vii	166.26 (8)	O1W—Li1—O2W—Li2	170.08 (5)
N1—S1—O1—Li2^vii	43.06 (9)	O2ⁱⁱ—Li1—O2W—Li2	−6.54 (6)
N2—S1—O1—Li2^vii	−69.93 (9)	Li1ⁱ—Li1—O2W—Li2	128.50 (7)
O1—S1—O2—Li1^viii	12.38 (6)	O4ⁱⁱⁱ—Li2—O2W—Li1	−99.68 (6)
N1—S1—O2—Li1^viii	136.11 (6)	O3^iv—Li2—O2W—Li1	99.83 (7)
N2—S1—O2—Li1^viii	−112.48 (6)	O1^v—Li2—O2W—Li1	−4.0 (6)
O1—S1—O2—Li2^viii	−132.04 (7)	O2ⁱⁱ—Li2—O2W—Li1	6.21 (6)
N1—S1—O2—Li2^viii	−8.31 (7)	O4^iv—Li2—O2W—Li1	177.11 (5)
N2—S1—O2—Li2^viii	103.09 (7)	Li2^vi—Li2—O2W—Li1	−145.31 (6)
O1—S1—N1—C1	−127.04 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N2^x	0.791 (16)	2.155 (16)	2.9428 (14)	175 (2)
O1W—H1WB···O1^xi	0.842 (17)	2.29 (2)	2.9971 (15)	142 (2)
O2W—H2WA···N2^xii	0.823 (16)	2.049 (16)	2.8712 (14)	175.7 (16)
O2W—H2WB···N1ⁱ	0.79 (2)	2.01 (2)	2.7947 (14)	168.7 (17)

Symmetry codes: (i) −x+1, −y, −z+1; (x) −x+2, −y, −z+2; (xi) −x+1, y−1/2, −z+3/2; (xii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Li₂(C₂N₂O₄S)(H₂O₂)]
M_r	198.01
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	110
a, b, c (Å)	7.239 (3), 11.185 (3), 9.786 (4)
β (°)	124.27 (2)
V (Å³)	654.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.41 × 0.24 × 0.24

Data collection
Diffractometer	Bruker–Nonius Kappa X8 APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.825, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	34710, 3899, 3575
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.955

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.065, 1.06
No. of reflections	3899
No. of parameters	134
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N2ⁱ	0.791 (16)	2.155 (16)	2.9428 (14)	175 (2)
O1W—H1WB···O1ⁱⁱ	0.842 (17)	2.29 (2)	2.9971 (15)	142 (2)
O2W—H2WA···N2ⁱⁱⁱ	0.823 (16)	2.049 (16)	2.8712 (14)	175.7 (16)
O2W—H2WB···N1^iv	0.79 (2)	2.01 (2)	2.7947 (14)	168.7 (17)

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+1, −y, −z+1.

Acknowledgements

This work is funded by the US DOE BATT Program (contract DE—AC02–05-CH11231). PDB would like to thank the Department of Chemistry of North Carolina State University and the State of North Carolina for funding the purchase of the APEXII diffractometer.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Lee, C.-H. & Kohn, H. (1990). J. Am. Chem. Soc. 55, 6098–6104. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wen, R., Komin, A., Street, R. & Carmack, M. (1975). J. Org. Chem. 40, 2743–2748. CrossRef CAS Google Scholar