Poly[μ-aqua-diaqua-(μ(2)-pyrazine-2,3-dicarboxyl-ato)dilithium(I)].

The asymmetric unit of the title compound, [Li(2)(C(6)H(2)N(2)O(4))(H(2)O)(3)](n), consists of two independent Li(+) cations, one pyrazine-2,3-dicarboxyl-ate dianion and three water mol-ecules. One of the Li(+) cations has a distorted tetra-hedral geometry, coordinated by one of the carboxyl-ate O atoms of the pyrazine-2,3-dicarboxyl-ate ligand and three O atoms from three water mol-ecules, whereas the other Li(+) cation has a distorted trigonal-bipyramidal geometry, coordinated by a carboxyl-ate O atom of a symmetry-related pyrazine-2,3-dicarboxyl-ate ligand, two water mol-ecules and a chelating pyrazine-2,3-dicarboxyl-ate ligand (by utilizing both N and O atoms) of an adjacent mol-ecule. The synthesis of a hydrated polymeric dinuclear lithium complex formed with two pyrazine-2,3-dicarboxylic acid ligands has been reported previously [Tombul et al. (2008a ▶). Acta Cryst. E64, m491-m492]. By comparision to the complex reported here, the dinuclear complex formed with two pyrazine-2,3-dicarboxylic acid ligands differs in the coordination geometry of both Li atoms. The crystal structure further features O-H⋯O and O-H⋯N hydrogen-bonding inter-actions involving the water mol-ecules and carboxyl-ate O atoms.

Related literature

For a general background to multidendate carboxylic acids, see: Erxleben (2003 ▶); Ye et al. (2005 ▶); Fei et al. (2006 ▶). For further information on pyrazine-2,3-dicarboxylic acid, see: Takusagawa & Shimada (1973 ▶); Richard et al. (1973 ▶); Nepveu et al. (1993 ▶). For further information on the synthesis of metal complexes with pyrazine-2,3-dicarboxylic acid ligand, see: Tombul & Güven (2009 ▶); Tombul et al. (2006 ▶, 2007 ▶, 2008b ▶). For a related structure of lithium with pyrazine-2,3-dicarb­oxylic acid ligand, see: Tombul et al. (2008a ▶). For Li—O bond distances, see: Chen et al. (2007 ▶); Kim et al. (2007 ▶). For Li—N bond lengths, see: Grossie et al. (2006 ▶); Boyd et al. (2002 ▶).

Experimental

Crystal data

[Li2(C6H2N2O4)(H2O)3]

M = 234.02

Monoclinic,

a = 7.487 (3) Å

b = 16.409 (8) Å

c = 7.958 (2) Å

β = 92.92 (3)°

V = 976.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 298 K

0.40 × 0.20 × 0.06 mm

Data collection

Rigaku AFC-7S diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.948, T max = 0.994

6366 measured reflections

6045 independent reflections

2427 reflections with I > 2σ(I)

R int = 0.120

3 standard reflections frequency: 150 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.211

S = 0.96

6045 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.54 e Å−3

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989 ▶); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molec­ular Structure Corporation, 1993 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050570/om2293sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050570/om2293Isup2.hkl

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

[Li2(C6H2N2O4)(H2O)3]	F(000) = 480
Mr = 234.02	Dx = 1.592 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.487 (3) Å	θ = 3.0–7.9°
b = 16.409 (8) Å	µ = 0.14 mm−1
c = 7.958 (2) Å	T = 298 K
β = 92.92 (3)°	Prism, yellow
V = 976.4 (7) Å3	0.4 × 0.2 × 0.06 mm
Z = 4

Rigaku diffractometer	2427 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.120
graphite	θmax = 40.0°, θmin = 2.7°
ω–2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→29
Tmin = 0.948, Tmax = 0.994	l = −14→14
6366 measured reflections	3 standard reflections every 150 reflections
6045 independent reflections	intensity decay: none

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0977P)2] where P = (Fo2 + 2Fc2)/3
6045 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.54 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
O1	−0.01123 (18)	0.24672 (8)	0.0505 (2)	0.0341 (3)
O2	0.06063 (17)	0.37715 (7)	0.09640 (16)	0.0236 (3)
O3	0.20616 (17)	0.43281 (7)	0.43623 (16)	0.0238 (3)
O4	0.39167 (18)	0.47554 (7)	0.24601 (18)	0.0277 (3)
O5	0.03262 (19)	0.56609 (8)	0.21735 (17)	0.0252 (3)
H5A	0.004 (4)	0.5875 (17)	0.129 (4)	0.043 (8)*
H5B	0.147 (5)	0.558 (2)	0.222 (4)	0.069 (10)*
O6	0.17467 (17)	0.58515 (8)	0.56590 (16)	0.0224 (2)
H6A	0.272 (4)	0.613 (2)	0.581 (4)	0.058 (9)*
H6B	0.206 (4)	0.5391 (19)	0.519 (3)	0.048 (8)*
O7	−0.2951 (2)	0.46974 (13)	0.0850 (2)	0.0479 (5)
H7A	−0.316 (5)	0.501 (2)	−0.004 (5)	0.082 (12)*
H7B	−0.394 (5)	0.465 (2)	0.139 (4)	0.064 (10)*
N1	0.29092 (19)	0.19673 (8)	0.21499 (19)	0.0228 (3)
N2	0.52735 (19)	0.30911 (9)	0.3651 (2)	0.0246 (3)
C1	0.0838 (2)	0.30153 (9)	0.1146 (2)	0.0195 (3)
C2	0.2524 (2)	0.27631 (9)	0.2158 (2)	0.0172 (3)
C3	0.4472 (3)	0.17365 (11)	0.2881 (3)	0.0296 (4)
H3	0.4761	0.1185	0.2920	0.036*
C4	0.5669 (2)	0.22967 (11)	0.3582 (3)	0.0300 (4)
H4	0.6777	0.2118	0.4017	0.036*
C5	0.3672 (2)	0.33240 (9)	0.2984 (2)	0.0171 (3)
C6	0.31766 (19)	0.42055 (9)	0.3264 (2)	0.0168 (3)
Li1	−0.0795 (5)	0.4524 (2)	0.2209 (4)	0.0289 (7)
Li2	−0.0490 (4)	0.63229 (18)	0.4210 (4)	0.0252 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0312 (7)	0.0205 (6)	0.0488 (9)	−0.0017 (5)	−0.0159 (6)	−0.0045 (6)
O2	0.0304 (6)	0.0161 (5)	0.0240 (6)	0.0064 (4)	−0.0028 (5)	−0.0005 (4)
O3	0.0310 (6)	0.0158 (5)	0.0257 (6)	0.0022 (4)	0.0123 (5)	0.0002 (4)
O4	0.0300 (6)	0.0176 (5)	0.0367 (7)	−0.0035 (4)	0.0129 (5)	0.0050 (5)
O5	0.0298 (6)	0.0255 (6)	0.0201 (6)	0.0068 (5)	0.0016 (5)	0.0034 (5)
O6	0.0224 (5)	0.0192 (5)	0.0253 (6)	−0.0002 (4)	−0.0005 (4)	−0.0020 (4)
O7	0.0300 (8)	0.0775 (14)	0.0371 (9)	0.0162 (8)	0.0109 (6)	0.0208 (9)
N1	0.0256 (7)	0.0129 (5)	0.0297 (7)	0.0026 (5)	−0.0004 (5)	−0.0022 (5)
N2	0.0191 (6)	0.0208 (6)	0.0334 (8)	0.0025 (5)	−0.0024 (5)	−0.0025 (5)
C1	0.0225 (7)	0.0161 (6)	0.0197 (7)	0.0025 (5)	−0.0008 (5)	−0.0017 (5)
C2	0.0178 (6)	0.0133 (5)	0.0209 (7)	0.0012 (5)	0.0024 (5)	−0.0005 (5)
C3	0.0296 (8)	0.0169 (7)	0.0417 (11)	0.0074 (6)	−0.0043 (7)	−0.0015 (7)
C4	0.0229 (7)	0.0224 (7)	0.0438 (11)	0.0083 (6)	−0.0060 (7)	−0.0020 (7)
C5	0.0180 (6)	0.0132 (5)	0.0201 (7)	0.0007 (5)	0.0022 (5)	0.0000 (5)
C6	0.0174 (6)	0.0120 (5)	0.0212 (7)	−0.0002 (4)	0.0016 (5)	0.0002 (5)
Li1	0.0367 (17)	0.0197 (13)	0.0312 (17)	0.0031 (12)	0.0100 (13)	0.0010 (12)
Li2	0.0300 (15)	0.0163 (12)	0.0294 (16)	0.0004 (11)	0.0045 (12)	0.0027 (11)

O5—Li1	2.046 (4)	N2—C4	1.338 (2)
O5—Li2	2.069 (4)	N2—C5	1.342 (2)
O5—H5B	0.87 (4)	C2—C5	1.400 (2)
O5—H5A	0.80 (3)	C2—C1	1.519 (2)
O4—C6	1.2517 (19)	C5—C6	1.513 (2)
O6—Li2	2.129 (4)	C4—C3	1.382 (3)
O6—H6A	0.87 (3)	C4—H4	0.9300
O6—H6B	0.88 (3)	C3—H3	0.9300
O1—C1	1.241 (2)	Li2—O1ii	1.942 (3)
O2—C1	1.260 (2)	Li2—O3iii	1.988 (3)
O2—Li1	1.927 (3)	Li2—N1ii	2.317 (4)
O3—C6	1.2552 (19)	Li1—O7	1.918 (4)
N1—C3	1.335 (2)	Li1—O6iii	1.973 (4)
N1—C2	1.337 (2)	O7—H7A	0.88 (4)
N1—Li2i	2.317 (4)	O7—H7B	0.88 (4)
Li1—O5—Li2	109.27 (14)	N1—C3—C4	121.58 (16)
Li1—O5—H5B	105 (2)	N1—C3—H3	119.2
Li2—O5—H5B	112 (2)	C4—C3—H3	119.2
Li1—O5—H5A	109 (2)	O1—C1—O2	126.41 (15)
Li2—O5—H5A	112 (2)	O1—C1—C2	117.66 (14)
H5B—O5—H5A	109 (3)	O2—C1—C2	115.79 (14)
Li1iii—O6—Li2	105.71 (15)	O4—C6—O3	124.60 (14)
Li1iii—O6—H6A	112 (2)	O4—C6—C5	119.72 (14)
Li2—O6—H6A	121 (2)	O3—C6—C5	115.64 (13)
Li1iii—O6—H6B	102.5 (18)	O1ii—Li2—O3iii	126.42 (18)
Li2—O6—H6B	107.5 (18)	O1ii—Li2—O5	121.53 (17)
H6A—O6—H6B	106 (3)	O3iii—Li2—O5	111.87 (15)
C1—O1—Li2i	121.88 (15)	O1ii—Li2—O6	96.70 (15)
C1—O2—Li1	130.35 (15)	O3iii—Li2—O6	88.14 (13)
C6—O3—Li2iii	138.22 (14)	O5—Li2—O6	88.74 (13)
C3—N1—C2	117.34 (14)	O1ii—Li2—N1ii	77.56 (12)
C3—N1—Li2i	136.14 (14)	O3iii—Li2—N1ii	92.34 (14)
C2—N1—Li2i	106.51 (13)	O5—Li2—N1ii	97.38 (14)
C4—N2—C5	117.17 (15)	O6—Li2—N1ii	173.18 (17)
N1—C2—C5	121.12 (14)	O7—Li1—O2	105.65 (18)
N1—C2—C1	115.90 (13)	O7—Li1—O6iii	101.58 (17)
C5—C2—C1	122.89 (13)	O2—Li1—O6iii	118.14 (18)
N2—C5—C2	120.88 (14)	O7—Li1—O5	101.05 (17)
N2—C5—C6	115.78 (13)	O2—Li1—O5	110.05 (17)
C2—C5—C6	123.27 (13)	O6iii—Li1—O5	117.60 (17)
N2—C4—C3	121.58 (16)	Li1—O7—H7A	130 (3)
N2—C4—H4	119.2	Li1—O7—H7B	115 (2)
C3—C4—H4	119.2	H7A—O7—H7B	109 (3)
C3—N1—C2—C5	−3.5 (2)	C5—C2—C1—O2	6.1 (2)
Li2i—N1—C2—C5	176.03 (15)	Li2iii—O3—C6—O4	174.97 (19)
C3—N1—C2—C1	173.33 (16)	Li2iii—O3—C6—C5	−7.5 (3)
Li2i—N1—C2—C1	−7.18 (18)	N2—C5—C6—O4	73.8 (2)
C4—N2—C5—C2	−4.0 (3)	C2—C5—C6—O4	−109.25 (19)
C4—N2—C5—C6	172.98 (16)	N2—C5—C6—O3	−103.86 (18)
N1—C2—C5—N2	6.5 (3)	C2—C5—C6—O3	73.1 (2)
C1—C2—C5—N2	−170.03 (15)	Li1—O5—Li2—O1ii	−174.09 (18)
N1—C2—C5—C6	−170.25 (15)	Li1—O5—Li2—O3iii	1.3 (2)
C1—C2—C5—C6	13.2 (2)	Li1—O5—Li2—O6	88.83 (16)
C5—N2—C4—C3	−1.1 (3)	Li1—O5—Li2—N1ii	−94.19 (16)
C2—N1—C3—C4	−1.6 (3)	Li1iii—O6—Li2—O1ii	105.93 (16)
Li2i—N1—C3—C4	179.05 (19)	Li1iii—O6—Li2—O3iii	−20.53 (16)
N2—C4—C3—N1	4.1 (3)	Li1iii—O6—Li2—O5	−132.46 (14)
Li2i—O1—C1—O2	176.24 (17)	C1—O2—Li1—O7	−101.2 (2)
Li2i—O1—C1—C2	0.7 (2)	C1—O2—Li1—O6iii	11.5 (3)
Li1—O2—C1—O1	87.8 (3)	C1—O2—Li1—O5	150.45 (16)
Li1—O2—C1—C2	−96.7 (2)	Li2—O5—Li1—O7	91.67 (18)
N1—C2—C1—O1	5.3 (2)	Li2—O5—Li1—O2	−156.99 (16)
C5—C2—C1—O1	−177.97 (16)	Li2—O5—Li1—O6iii	−17.8 (2)
N1—C2—C1—O2	−170.67 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2iv	0.81 (3)	1.92 (3)	2.723 (3)	172.60 (3)
O5—H5B···O4	0.87 (4)	2.28 (4)	3.068 (3)	152 (3)
O6—H6A···N2v	0.86 (3)	2.00 (3)	2.857 (3)	169.66 (4)
O6—H6B···O3	0.88 (3)	1.86 (3)	2.719 (3)	163 (3)
O7—H7A···O4iv	0.88 (4)	2.02 (4)	2.841 (3)	154.89 (6)
O7—H7B···O4vi	0.88 (4)	1.86 (4)	2.730 (3)	169.51 (6)

Table 1

Selected bond lengths (Å)

O5—Li1	2.046 (4)
O5—Li2	2.069 (4)
O6—Li2	2.129 (4)
O2—Li1	1.927 (3)
N1—Li2i	2.317 (4)
Li2—O1ii	1.942 (3)
Li2—O3iii	1.988 (3)
Li1—O7	1.918 (4)
Li1—O6iii	1.973 (4)

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

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2iv	0.81 (3)	1.92 (3)	2.723 (3)	172.60 (3)
O5—H5B⋯O4	0.87 (4)	2.28 (4)	3.068 (3)	152 (3)
O6—H6A⋯N2v	0.86 (3)	2.00 (3)	2.857 (3)	169.66 (4)
O6—H6B⋯O3	0.88 (3)	1.86 (3)	2.719 (3)	163 (3)
O7—H7A⋯O4iv	0.88 (4)	2.02 (4)	2.841 (3)	154.89 (6)
O7—H7B⋯O4vi	0.88 (4)	1.86 (4)	2.730 (3)	169.51 (6)

Symmetry codes: (iv) ; (v) ; (vi) .