Poly[(μ4-3-carb­oxy­pyrazine-2-carboxyl­ato)(μ4-nitrato)dilithium]

Starosta, W.; Leciejewicz, J.

doi:10.1107/S1600536812050738

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page m62

https://doi.org/10.1107/S1600536812050738

Open

access

Poly[(μ₄-3-carboxypyrazine-2-carboxylato)(μ₄-nitrato)dilithium]

Wojciech Starosta ^a and Janusz Leciejewicz ^a ^*

^aInstitute of Nuclear Chemistry and Technology, ul. Dorodna 16, 03-195 Warszawa, Poland
^*Correspondence e-mail: j.leciejewicz@ichtj.waw.pl

(Received 9 December 2012; accepted 13 December 2012; online 19 December 2012)

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 molecular 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 intramolecular 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_r = 241.99
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.084
S = 1.10
2572 reflections
167 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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—O5^iv	2.014 (3)
Li2—O6^v	2.040 (4)
Li2—O3	2.086 (3)
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (v) $[-x, y-{\script{1\over 2}}, -z]$ .

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)

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812050738/kp2442sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050738/kp2442Isup2.hkl

checkCIF report

Comment top

Pyrazine-2,3-dicarboxylate dianion shows large versality in forming coordination compounds with metal ions. Depending on the adopted chemical synthesis procedures, compounds with a number of different polymeric structures have been observed, as for example, in the case of the Ca(II) ion (Ptasiewicz-Bąk & Leciejewicz, 1997; Starosta & Leciejewicz, 2004, 2005a, 2005b). Polymeric structures of three Li^I complexes with the title ligand have been reported (Tombul et al., 2008; Tombul & Güven, 2009; Starosta & Leciejewicz, 2011). Recently we have obtained a new compund with the title ligand. The asymmetric unit of the title compound contains two symmetry independent Li^I ions. Each shows a distorted trigonal-bipyramidal coordination geometry. The Li1 ion is coordinated by ligand N1,O1 bonding group, a carboxylato O3ⁱⁱ atom from the adjacent ligand and O5 and O7ⁱ atoms from two different nitrate ions. The O1, O5, O7ⁱ atoms form a base, the Li1 ion is 0.1572 (3) Å out of this plane; N1 and O3ⁱⁱ atoms are at the axial positions. The same coordination geometry shows the Li2 ion which is situated 0.3616 (3) Å out of the equatorial plane composed of N4, O1ⁱⁱⁱ and O6^v atoms, while the O3 and O5^iv atoms form the apices. The observed Li—O and Li—N bond distances are typical of Li^I complexes with diazine carboxylate ligands. Ligand carboxylate O2 and O4 atoms remain coordination inactive. Fourier maps indicate clearly, that the O2 atom is protonated acting as a donor in a low-barrier intramolecular hydrogen bond of 2.3955 (19) Å to the O4 atom suggesting a partial proton transfer(Table 2). The ligand is monovalent and with the nitrate anion maintains the charge balance in the structure. Pyrazine ring is planar with r.m.s. of 0.0051 (2) Å; carboxylate groups C7/O1/O2 and C8/O3/O4 form with it dihedral angles of 8.4 (1)° and 12.5 (1)°, respectively. Ligand molecule bridges metal ions in µ₄ mode. Li1 and Li2 ions are chelated by both N,O groups of a ligand and bidentate O1ⁱⁱ and O3ⁱⁱatoms [Fig. 1]. A dimeric moiety Li1/O1/L2ⁱⁱ/O3ⁱⁱⁱ constitutes a link in a bridging pathway formed by ligand molecules, giving rise to molecular ribbons propagating in the [010] direction. A nitrate anion with r.m.s. of 0.0016 (1) Å acts also in the µ₄ mode and forms the other bridging pathway: while the O6 atom coordinates the Li2^v and the O7 atom - the Li1^iv ion, the O5 atom acts as bidentate bridging to the Li1 and Li2ⁱⁱⁱ ions giving rise to a three-dimensional framework (Fig. 2).

Related literature top

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 top

An aqueous solution containing 1 mmol of lithium(I) nitrate and 1 mmol of pyrazine-2,3-dicarboxylic acid dihydrate was boiled with stirring under reflux for 6 h. After cooling to room temperature three drops of 1 N nitric acid were added to maintain pH of 5. Then the solution was left to evaporate to dryness. Deposited single crystal plates were washed with cold ethanol and dried in the air.

Structure description top

# Used for convenience to store draft or replaced versions # of the abstract, comment etc. # Its contents will not be output

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A fragment of the structure of the title compound with atom labelling scheme and 50% probability displacement ellipsoids. Symmetry code: (i) x + 1, y, z; (ii) -x + 1, y + 1/2, -z + 2; (iii) -x + 1, y - 1/2, -z + 2; (iv) -x + 1, y - 1/2, -z + 1; (v) -x, y - 1/2, -z + 1.
	Fig. 2. The packing of molecular ribbons in the structure of the title compound showing nitrate bridging mode.

Poly[(µ₄-3-carboxypyrazine-2-carboxylato)(µ₄-nitrato)dilithium] top

Crystal data top

[Li₂(C₆H₃N₂O₄)₂(NO₃)]	F(000) = 242
M_r = 241.99	D_x = 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

Data collection top

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	R_int = 0.015
Detector resolution: 16.0131 pixels mm^-1	θ_max = 30.7°, θ_min = 3.3°
ω scans	h = −5→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −21→22
T_min = 0.936, T_max = 1.000	l = −5→8
4032 measured reflections

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)] = 0.036	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(F_o²) + (0.0337P)² + 0.0702P] where P = (F_o² + 2F_c²)/3
2572 reflections	(Δ/σ)_max < 0.001
167 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

[Li₂(C₆H₃N₂O₄)₂(NO₃)]	V = 450.69 (2) Å³
M_r = 241.99	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.6273 (1) Å	µ = 0.16 mm⁻¹
b = 15.8565 (3) Å	T = 293 K
c = 6.1719 (2) Å	0.20 × 0.14 × 0.12 mm
β = 95.598 (2)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer	2572 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2401 reflections with I > 2σ(I)
T_min = 0.936, T_max = 1.000	R_int = 0.015
4032 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.21 e Å⁻³
2572 reflections	Δρ_min = −0.20 e Å⁻³
167 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—Li1^iv	1.994 (3)
Li1—O7ⁱⁱ	1.994 (3)	O6—Li2^v	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—O1^vi	1.989 (3)
N4—C5	1.324 (2)	Li2—O5^vii	2.014 (3)
N4—C3	1.351 (2)	Li2—O6^viii	2.040 (4)
Li2—N4	2.176 (3)	Li2—O3	2.086 (3)
N1—C6	1.319 (2)	Li2—Li1^vi	3.011 (4)
N2—O6	1.231 (2)	O3—Li1^vi	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)	O1^vi—Li2—O5^vii	102.31 (15)
O7—N2—O5	118.93 (15)	O1^vi—Li2—O6^viii	104.59 (16)
C7—O2—H1	114 (2)	O5^vii—Li2—O6^viii	94.18 (14)
O3—C8—O4	124.69 (17)	O1^vi—Li2—O3	84.81 (13)
O3—C8—C3	116.47 (15)	O5^vii—Li2—O3	171.64 (18)
O4—C8—C3	118.83 (14)	O6^viii—Li2—O3	88.17 (14)
N4—C3—C2	119.89 (14)	O1^vi—Li2—N4	141.01 (18)
N4—C3—C8	111.18 (14)	O5^vii—Li2—N4	97.16 (14)
C2—C3—C8	128.92 (14)	O6^viii—Li2—N4	107.32 (15)
N2—O7—Li1^iv	131.81 (15)	O3—Li2—N4	74.49 (12)
N2—O6—Li2^v	139.98 (15)	O1^vi—Li2—Li1^vi	43.63 (9)
N4—C5—C6	121.23 (16)	O5^vii—Li2—Li1^vi	145.93 (15)
N4—C5—H5	119.4	O6^viii—Li2—Li1^vi	94.92 (13)
C6—C5—H5	119.4	O3—Li2—Li1^vi	41.41 (9)
O1—C7—O2	123.79 (16)	N4—Li2—Li1^vi	111.21 (14)
O1—C7—C2	116.83 (15)	C8—O3—Li1^vi	142.15 (15)
O2—C7—C2	119.38 (15)	C8—O3—Li2	119.94 (14)
N1—C6—C5	120.92 (17)	Li1^vi—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—Li1^iv	−32.3 (3)	C2—N1—Li1—Li2ⁱ	21.8 (2)
O5—N2—O7—Li1^iv	148.58 (19)	C5—N4—Li2—O1^vi	112.0 (3)
O7—N2—O6—Li2^v	1.3 (3)	C3—N4—Li2—O1^vi	−65.4 (3)
O5—N2—O6—Li2^v	−179.55 (19)	C5—N4—Li2—O5^vii	−7.8 (2)
C3—N4—C5—C6	0.9 (3)	C3—N4—Li2—O5^vii	174.83 (14)
Li2—N4—C5—C6	−176.40 (18)	C5—N4—Li2—O6^viii	−104.4 (2)
Li2ⁱ—O1—C7—O2	9.4 (4)	C3—N4—Li2—O6^viii	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—Li1^vi	153.02 (18)
N1—C2—C7—O1	−7.9 (2)	C3—N4—Li2—Li1^vi	−24.4 (2)
C3—C2—C7—O1	170.27 (18)	O4—C8—O3—Li1^vi	−43.1 (4)
N1—C2—C7—O2	172.51 (18)	C3—C8—O3—Li1^vi	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)	O1^vi—Li2—O3—C8	159.34 (16)
N4—C5—C6—N1	−1.2 (3)	O5^vii—Li2—O3—C8	10.7 (14)
N2—O5—Li1—O7ⁱⁱ	158.55 (14)	O6^viii—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)	Li1^vi—Li2—O3—C8	164.6 (2)
Li2ⁱⁱⁱ—O5—Li1—O3ⁱ	99.13 (17)	O1^vi—Li2—O3—Li1^vi	−5.27 (15)
N2—O5—Li1—O1	−8.1 (2)	O5^vii—Li2—O3—Li1^vi	−153.9 (13)
Li2ⁱⁱⁱ—O5—Li1—O1	−171.75 (15)	O6^viii—Li2—O3—Li1^vi	99.55 (14)
N2—O5—Li1—N1	69.12 (17)	N4—Li2—O3—Li1^vi	−151.90 (13)
Li2ⁱⁱⁱ—O5—Li1—N1	−94.52 (18)

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

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Li₂(C₆H₃N₂O₄)₂(NO₃)]
M_r	241.99
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	4.6273 (1), 15.8565 (3), 6.1719 (2)
β (°)	95.598 (2)
V (Å³)	450.69 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.20 × 0.14 × 0.12

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Eos)
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.936, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4032, 2572, 2401
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.719

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.084, 1.10
No. of reflections	2572
No. of parameters	167
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Li1—O1	2.086 (3)	Li2—N4	2.176 (3)
Li1—O5	2.005 (3)	Li2—O1ⁱⁱⁱ	1.989 (3)
Li1—N1	2.158 (3)	Li2—O5^iv	2.014 (3)
Li1—O7ⁱ	1.994 (3)	Li2—O6^v	2.040 (4)
Li1—O3ⁱⁱ	1.999 (3)	Li2—O3	2.086 (3)

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

Hydrogen-bond geometry (Å, º) top

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)

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Ptasiewicz-Bąk, H. & Leciejewicz, J. (1997). Pol. J. Chem. 71, 1603–1610. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Starosta, W. & Leciejewicz, J. (2004). J. Coord. Chem. 57, 1151–1156. Web of Science CSD CrossRef CAS Google Scholar
Starosta, W. & Leciejewicz, J. (2005a). J. Coord. Chem. 58, 891–898. Web of Science CSD CrossRef CAS Google Scholar
Starosta, W. & Leciejewicz, J. (2005b). J. Coord. Chem. 58, 963–968. Web of Science CSD CrossRef CAS Google Scholar
Starosta, W. & Leciejewicz, J. (2011). Acta Cryst. E67, m1133–m1134. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Tombul, M. & Guven, K. (2009). Acta Cryst. E65, m1704–m1705. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Tombul, M., Güven, K. & Büyükgüngör, O. (2008). Acta Cryst. E64, m491–m492. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page m62

https://doi.org/10.1107/S1600536812050738

Open

access