Poly[(μ4-3-carb-oxy-pyrazine-2-carboxyl-ato)(μ4-nitrato)dilithium].

In the title compound, [Li2(C6H3N2O4)2(NO3)] n , the two symmetry-independent Li(I) ions are each in a trigonal-bipyramidal coordination and are bridged by N,O-bonding ligands, forming mol-ecular ribbons propagating in [010]. Each Li(I) ion is also coordinated by two O atoms from nitrate ions, connecting the ribbons into a three-dimensional network. Very strong intra-molecular O-H⋯O hydrogen bonds occur between the carboxyl and the carboxylate group.

Related literature

For three structures of lithium(I) complexes with pyrazine-2,3-dicarboxyl­ate and water ligands, see: Tombul et al. (2008 ▶); Tombul & Güven (2009) ▶; Starosta & Leciejewicz (2011 ▶). For structures of calcium(II) complexes with the title ligand, see: Ptasiewicz-Bąk & Leciejewicz (1997 ▶); Starosta & Leciejewicz (2004 ▶, 2005a ▶,b ▶).

Experimental

Crystal data

[Li2(C6H3N2O4)2(NO3)]

M = 241.99

Monoclinic,

a = 4.6273 (1) Å

b = 15.8565 (3) Å

c = 6.1719 (2) Å

β = 95.598 (2)°

V = 450.69 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 293 K

0.20 × 0.14 × 0.12 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.936, T max = 1.000

4032 measured reflections

2572 independent reflections

2401 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.084

S = 1.10

2572 reflections

167 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050738/kp2442sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050738/kp2442Isup2.hkl

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

[Li2(C6H3N2O4)2(NO3)]	F(000) = 242
Mr = 241.99	Dx = 1.783 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2509 reflections
a = 4.6273 (1) Å	θ = 3.3–30.7°
b = 15.8565 (3) Å	µ = 0.16 mm−1
c = 6.1719 (2) Å	T = 293 K
β = 95.598 (2)°	Block, colourless
V = 450.69 (2) Å3	0.20 × 0.14 × 0.12 mm
Z = 2

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer	2572 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2401 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.015
Detector resolution: 16.0131 pixels mm-1	θmax = 30.7°, θmin = 3.3°
ω scans	h = −5→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −21→22
Tmin = 0.936, Tmax = 1.000	l = −5→8
4032 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0337P)2 + 0.0702P] where P = (Fo2 + 2Fc2)/3
2572 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.20 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	0.5316 (3)	0.40681 (8)	0.6101 (2)	0.0322 (3)
O5	0.4586 (3)	0.48672 (8)	0.0630 (2)	0.0297 (3)
C2	0.4874 (4)	0.27654 (10)	0.4273 (3)	0.0223 (3)
N4	0.5051 (4)	0.14644 (9)	0.2348 (2)	0.0279 (3)
N1	0.6499 (3)	0.31421 (9)	0.2871 (2)	0.0278 (3)
N2	0.1867 (3)	0.47658 (9)	0.0539 (2)	0.0243 (3)
O2	0.2330 (4)	0.31513 (9)	0.7378 (3)	0.0427 (4)
C8	0.2425 (4)	0.13507 (11)	0.5462 (3)	0.0261 (3)
C3	0.4152 (4)	0.19074 (10)	0.4027 (3)	0.0228 (3)
O7	0.0838 (3)	0.43786 (9)	0.2022 (3)	0.0393 (3)
O6	0.0354 (3)	0.50501 (10)	−0.1046 (2)	0.0388 (3)
C5	0.6615 (4)	0.18550 (12)	0.0970 (3)	0.0326 (4)
H5	0.7223	0.1559	−0.0205	0.039*
C7	0.4118 (4)	0.33782 (11)	0.6048 (3)	0.0267 (3)
C6	0.7368 (5)	0.27000 (11)	0.1245 (3)	0.0338 (4)
H6	0.8500	0.2957	0.0269	0.041*
Li1	0.7058 (7)	0.44849 (19)	0.3298 (5)	0.0289 (6)
Li2	0.3903 (7)	0.0133 (2)	0.2244 (5)	0.0300 (6)
O3	0.2524 (3)	0.05895 (8)	0.5143 (2)	0.0329 (3)
O4	0.1008 (4)	0.16985 (8)	0.6880 (3)	0.0444 (4)
H1	0.153 (8)	0.252 (2)	0.713 (6)	0.093 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0444 (8)	0.0222 (6)	0.0311 (7)	−0.0058 (6)	0.0086 (6)	−0.0054 (5)
O5	0.0184 (5)	0.0402 (7)	0.0307 (6)	−0.0033 (5)	0.0045 (4)	0.0052 (5)
C2	0.0242 (7)	0.0194 (7)	0.0236 (7)	0.0013 (6)	0.0044 (6)	0.0004 (6)
N4	0.0352 (8)	0.0224 (7)	0.0275 (8)	−0.0012 (6)	0.0092 (6)	−0.0022 (6)
N1	0.0337 (8)	0.0208 (6)	0.0303 (8)	−0.0019 (6)	0.0103 (6)	0.0006 (6)
N2	0.0223 (6)	0.0230 (6)	0.0285 (7)	−0.0014 (5)	0.0073 (5)	−0.0009 (5)
O2	0.0596 (9)	0.0274 (6)	0.0463 (9)	−0.0092 (7)	0.0320 (7)	−0.0110 (6)
C8	0.0308 (9)	0.0230 (8)	0.0249 (9)	−0.0012 (7)	0.0039 (7)	0.0008 (6)
C3	0.0237 (8)	0.0214 (7)	0.0239 (8)	0.0003 (6)	0.0050 (6)	0.0017 (6)
O7	0.0332 (7)	0.0416 (8)	0.0461 (8)	0.0019 (6)	0.0197 (6)	0.0144 (6)
O6	0.0280 (7)	0.0479 (8)	0.0392 (7)	−0.0007 (6)	−0.0036 (6)	0.0101 (6)
C5	0.0433 (10)	0.0271 (9)	0.0301 (9)	0.0005 (8)	0.0173 (8)	−0.0051 (7)
C7	0.0322 (9)	0.0217 (7)	0.0265 (8)	0.0010 (6)	0.0045 (7)	−0.0022 (6)
C6	0.0426 (11)	0.0258 (8)	0.0356 (10)	−0.0016 (8)	0.0171 (8)	0.0032 (7)
Li1	0.0342 (16)	0.0249 (14)	0.0288 (15)	0.0009 (12)	0.0097 (12)	0.0000 (12)
Li2	0.0382 (16)	0.0234 (13)	0.0287 (15)	0.0015 (13)	0.0052 (13)	0.0008 (12)
O3	0.0495 (8)	0.0207 (6)	0.0293 (6)	−0.0037 (5)	0.0085 (6)	0.0027 (5)
O4	0.0629 (10)	0.0275 (7)	0.0488 (9)	−0.0113 (7)	0.0359 (8)	−0.0059 (6)

O1—C7	1.225 (2)	O2—C7	1.273 (2)
O1—Li2i	1.989 (3)	O2—H1	1.07 (4)
Li1—O1	2.086 (3)	C8—O3	1.224 (2)
O5—N2	1.2643 (18)	C8—O4	1.269 (2)
Li1—O5	2.005 (3)	C8—C3	1.530 (2)
Li1—N1	2.158 (3)	O7—Li1iv	1.994 (3)
Li1—O7ii	1.994 (3)	O6—Li2v	2.040 (4)
Li1—O3i	1.999 (3)	C5—C6	1.391 (3)
O5—Li2iii	2.014 (3)	C5—H5	0.9300
C2—N1	1.341 (2)	C6—H6	0.9300
C2—C3	1.406 (2)	Li1—Li2i	3.011 (4)
C2—C7	1.530 (2)	Li2—O1vi	1.989 (3)
N4—C5	1.324 (2)	Li2—O5vii	2.014 (3)
N4—C3	1.351 (2)	Li2—O6viii	2.040 (4)
Li2—N4	2.176 (3)	Li2—O3	2.086 (3)
N1—C6	1.319 (2)	Li2—Li1vi	3.011 (4)
N2—O6	1.231 (2)	O3—Li1vi	1.999 (3)
N2—O7	1.2359 (19)	O4—H1	1.34 (4)
C7—O1—Li2i	146.19 (15)	C5—C6—H6	119.5
C7—O1—Li1	118.12 (15)	O7ii—Li1—O3i	102.51 (15)
Li2i—O1—Li1	95.24 (14)	O7ii—Li1—O5	98.83 (14)
N2—O5—Li1	118.93 (13)	O3i—Li1—O5	98.69 (14)
N2—O5—Li2iii	114.63 (14)	O7ii—Li1—O1	136.49 (18)
Li1—O5—Li2iii	124.59 (14)	O3i—Li1—O1	84.57 (13)
N1—C2—C3	120.27 (14)	O5—Li1—O1	122.78 (17)
N1—C2—C7	111.15 (14)	O7ii—Li1—N1	88.16 (13)
C3—C2—C7	128.55 (15)	O3i—Li1—N1	158.15 (18)
C5—N4—C3	118.59 (14)	O5—Li1—N1	98.41 (14)
C5—N4—Li2	125.60 (15)	O1—Li1—N1	74.76 (11)
C3—N4—Li2	115.76 (14)	O7ii—Li1—Li2i	127.08 (16)
C6—N1—C2	119.08 (15)	O3i—Li1—Li2i	43.67 (9)
C6—N1—Li1	125.14 (14)	O5—Li1—Li2i	121.60 (15)
C2—N1—Li1	115.41 (13)	O1—Li1—Li2i	41.13 (9)
O6—N2—O7	122.70 (15)	N1—Li1—Li2i	114.95 (13)
O6—N2—O5	118.37 (14)	O1vi—Li2—O5vii	102.31 (15)
O7—N2—O5	118.93 (15)	O1vi—Li2—O6viii	104.59 (16)
C7—O2—H1	114 (2)	O5vii—Li2—O6viii	94.18 (14)
O3—C8—O4	124.69 (17)	O1vi—Li2—O3	84.81 (13)
O3—C8—C3	116.47 (15)	O5vii—Li2—O3	171.64 (18)
O4—C8—C3	118.83 (14)	O6viii—Li2—O3	88.17 (14)
N4—C3—C2	119.89 (14)	O1vi—Li2—N4	141.01 (18)
N4—C3—C8	111.18 (14)	O5vii—Li2—N4	97.16 (14)
C2—C3—C8	128.92 (14)	O6viii—Li2—N4	107.32 (15)
N2—O7—Li1iv	131.81 (15)	O3—Li2—N4	74.49 (12)
N2—O6—Li2v	139.98 (15)	O1vi—Li2—Li1vi	43.63 (9)
N4—C5—C6	121.23 (16)	O5vii—Li2—Li1vi	145.93 (15)
N4—C5—H5	119.4	O6viii—Li2—Li1vi	94.92 (13)
C6—C5—H5	119.4	O3—Li2—Li1vi	41.41 (9)
O1—C7—O2	123.79 (16)	N4—Li2—Li1vi	111.21 (14)
O1—C7—C2	116.83 (15)	C8—O3—Li1vi	142.15 (15)
O2—C7—C2	119.38 (15)	C8—O3—Li2	119.94 (14)
N1—C6—C5	120.92 (17)	Li1vi—O3—Li2	94.92 (14)
N1—C6—H6	119.5	C8—O4—H1	113.8 (17)
C3—C2—N1—C6	1.0 (3)	N2—O5—Li1—Li2i	−57.2 (2)
C7—C2—N1—C6	179.39 (16)	Li2iii—O5—Li1—Li2i	139.21 (19)
C3—C2—N1—Li1	174.35 (15)	C7—O1—Li1—O7ii	−88.5 (3)
C7—C2—N1—Li1	−7.3 (2)	Li2i—O1—Li1—O7ii	97.2 (3)
Li1—O5—N2—O6	175.52 (16)	C7—O1—Li1—O3i	168.99 (15)
Li2iii—O5—N2—O6	−19.3 (2)	Li2i—O1—Li1—O3i	−5.28 (15)
Li1—O5—N2—O7	−5.3 (2)	C7—O1—Li1—O5	72.1 (2)
Li2iii—O5—N2—O7	159.91 (16)	Li2i—O1—Li1—O5	−102.13 (19)
C5—N4—C3—C2	0.3 (3)	C7—O1—Li1—N1	−18.14 (18)
Li2—N4—C3—C2	177.86 (16)	Li2i—O1—Li1—N1	167.59 (13)
C5—N4—C3—C8	−179.02 (17)	C7—O1—Li1—Li2i	174.3 (2)
Li2—N4—C3—C8	−1.4 (2)	C6—N1—Li1—O7ii	−34.8 (2)
N1—C2—C3—N4	−1.3 (3)	C2—N1—Li1—O7ii	152.34 (15)
C7—C2—C3—N4	−179.31 (17)	C6—N1—Li1—O3i	−155.0 (4)
N1—C2—C3—C8	177.86 (17)	C2—N1—Li1—O3i	32.2 (6)
C7—C2—C3—C8	−0.2 (3)	C6—N1—Li1—O5	63.8 (2)
O3—C8—C3—N4	12.0 (2)	C2—N1—Li1—O5	−109.00 (16)
O4—C8—C3—N4	−167.97 (17)	C6—N1—Li1—O1	−174.35 (17)
O3—C8—C3—C2	−167.18 (17)	C2—N1—Li1—O1	12.80 (17)
O4—C8—C3—C2	12.8 (3)	C6—N1—Li1—Li2i	−165.38 (18)
O6—N2—O7—Li1iv	−32.3 (3)	C2—N1—Li1—Li2i	21.8 (2)
O5—N2—O7—Li1iv	148.58 (19)	C5—N4—Li2—O1vi	112.0 (3)
O7—N2—O6—Li2v	1.3 (3)	C3—N4—Li2—O1vi	−65.4 (3)
O5—N2—O6—Li2v	−179.55 (19)	C5—N4—Li2—O5vii	−7.8 (2)
C3—N4—C5—C6	0.9 (3)	C3—N4—Li2—O5vii	174.83 (14)
Li2—N4—C5—C6	−176.40 (18)	C5—N4—Li2—O6viii	−104.4 (2)
Li2i—O1—C7—O2	9.4 (4)	C3—N4—Li2—O6viii	78.16 (19)
Li1—O1—C7—O2	−160.34 (19)	C5—N4—Li2—O3	172.54 (18)
Li2i—O1—C7—C2	−170.2 (2)	C3—N4—Li2—O3	−4.88 (16)
Li1—O1—C7—C2	20.1 (2)	C5—N4—Li2—Li1vi	153.02 (18)
N1—C2—C7—O1	−7.9 (2)	C3—N4—Li2—Li1vi	−24.4 (2)
C3—C2—C7—O1	170.27 (18)	O4—C8—O3—Li1vi	−43.1 (4)
N1—C2—C7—O2	172.51 (18)	C3—C8—O3—Li1vi	136.9 (2)
C3—C2—C7—O2	−9.3 (3)	O4—C8—O3—Li2	162.41 (19)
C2—N1—C6—C5	0.2 (3)	C3—C8—O3—Li2	−17.6 (2)
Li1—N1—C6—C5	−172.44 (19)	O1vi—Li2—O3—C8	159.34 (16)
N4—C5—C6—N1	−1.2 (3)	O5vii—Li2—O3—C8	10.7 (14)
N2—O5—Li1—O7ii	158.55 (14)	O6viii—Li2—O3—C8	−95.84 (18)
Li2iii—O5—Li1—O7ii	−5.1 (2)	N4—Li2—O3—C8	12.71 (19)
N2—O5—Li1—O3i	−97.24 (17)	Li1vi—Li2—O3—C8	164.6 (2)
Li2iii—O5—Li1—O3i	99.13 (17)	O1vi—Li2—O3—Li1vi	−5.27 (15)
N2—O5—Li1—O1	−8.1 (2)	O5vii—Li2—O3—Li1vi	−153.9 (13)
Li2iii—O5—Li1—O1	−171.75 (15)	O6viii—Li2—O3—Li1vi	99.55 (14)
N2—O5—Li1—N1	69.12 (17)	N4—Li2—O3—Li1vi	−151.90 (13)
Li2iii—O5—Li1—N1	−94.52 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O4	1.07 (4)	1.34 (4)	2.3955 (19)	170 (4)

Table 1

Selected bond lengths (Å)

Li1—O1	2.086 (3)
Li1—O5	2.005 (3)
Li1—N1	2.158 (3)
Li1—O7i	1.994 (3)
Li1—O3ii	1.999 (3)
Li2—N4	2.176 (3)
Li2—O1iii	1.989 (3)
Li2—O5iv	2.014 (3)
Li2—O6v	2.040 (4)
Li2—O3	2.086 (3)

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

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O4	1.07 (4)	1.34 (4)	2.3955 (19)	170 (4)