Poly[(μ₄-3-carb­oxy­pyrazine-2-carboxyl­ato)(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 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.084
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT303_ALERT_2_C Full Occupancy H-Atom  H1     with # Connections       2.00
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C2     -   C7     ...       1.53 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C3     -   C8     ...       1.53 Ang.
PLAT772_ALERT_2_C Suspect O-H Bond in CIF:   O4     --  H1      ..       1.34 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................         88 Perc.

Alert level G
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          3
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         82
            O5  -LI2 -O3  -C8     10.70  1.40   2.645   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         87
            O5  -LI2 -O3  -LI1  -153.90  1.30   2.645   1.555   1.555   2.646
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.28 Ratio
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         77

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   2 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

The hydrogen atom of carboxylate group was located in a difference map and was refined independently with an isotropic displacement parameter. H atoms bonded to pyrazine ring C atoms were placed in calculated positions with C—H = 0.93 and 0.96 Å and treated as riding on the parent atoms with U_iso(H)= 1.2U_eq(C).

Computing details

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

	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]

Crystal data

[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) Å^3	0.20 × 0.14 × 0.12 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0337P)^2 + 0.0702P] where P = (Fo^2 + 2Fc^2)/3
2572 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.21 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C7	1.225 (2)	O2—C7	1.273 (2)
O1—Li2^i	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—O7^ii	1.994 (3)	O6—Li2^v	2.040 (4)
Li1—O3^i	1.999 (3)	C5—C6	1.391 (3)
O5—Li2^iii	2.014 (3)	C5—H5	0.9300
C2—N1	1.341 (2)	C6—H6	0.9300
C2—C3	1.406 (2)	Li1—Li2^i	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—Li2^i	146.19 (15)	C5—C6—H6	119.5
C7—O1—Li1	118.12 (15)	O7^ii—Li1—O3^i	102.51 (15)
Li2^i—O1—Li1	95.24 (14)	O7^ii—Li1—O5	98.83 (14)
N2—O5—Li1	118.93 (13)	O3^i—Li1—O5	98.69 (14)
N2—O5—Li2^iii	114.63 (14)	O7^ii—Li1—O1	136.49 (18)
Li1—O5—Li2^iii	124.59 (14)	O3^i—Li1—O1	84.57 (13)
N1—C2—C3	120.27 (14)	O5—Li1—O1	122.78 (17)
N1—C2—C7	111.15 (14)	O7^ii—Li1—N1	88.16 (13)
C3—C2—C7	128.55 (15)	O3^i—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)	O7^ii—Li1—Li2^i	127.08 (16)
C6—N1—C2	119.08 (15)	O3^i—Li1—Li2^i	43.67 (9)
C6—N1—Li1	125.14 (14)	O5—Li1—Li2^i	121.60 (15)
C2—N1—Li1	115.41 (13)	O1—Li1—Li2^i	41.13 (9)
O6—N2—O7	122.70 (15)	N1—Li1—Li2^i	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—Li2^i	−57.2 (2)
C7—C2—N1—C6	179.39 (16)	Li2^iii—O5—Li1—Li2^i	139.21 (19)
C3—C2—N1—Li1	174.35 (15)	C7—O1—Li1—O7^ii	−88.5 (3)
C7—C2—N1—Li1	−7.3 (2)	Li2^i—O1—Li1—O7^ii	97.2 (3)
Li1—O5—N2—O6	175.52 (16)	C7—O1—Li1—O3^i	168.99 (15)
Li2^iii—O5—N2—O6	−19.3 (2)	Li2^i—O1—Li1—O3^i	−5.28 (15)
Li1—O5—N2—O7	−5.3 (2)	C7—O1—Li1—O5	72.1 (2)
Li2^iii—O5—N2—O7	159.91 (16)	Li2^i—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)	Li2^i—O1—Li1—N1	167.59 (13)
C5—N4—C3—C8	−179.02 (17)	C7—O1—Li1—Li2^i	174.3 (2)
Li2—N4—C3—C8	−1.4 (2)	C6—N1—Li1—O7^ii	−34.8 (2)
N1—C2—C3—N4	−1.3 (3)	C2—N1—Li1—O7^ii	152.34 (15)
C7—C2—C3—N4	−179.31 (17)	C6—N1—Li1—O3^i	−155.0 (4)
N1—C2—C3—C8	177.86 (17)	C2—N1—Li1—O3^i	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—Li2^i	−165.38 (18)
O6—N2—O7—Li1^iv	−32.3 (3)	C2—N1—Li1—Li2^i	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)
Li2^i—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)
Li2^i—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—O7^ii	158.55 (14)	O6^viii—Li2—O3—C8	−95.84 (18)
Li2^iii—O5—Li1—O7^ii	−5.1 (2)	N4—Li2—O3—C8	12.71 (19)
N2—O5—Li1—O3^i	−97.24 (17)	Li1^vi—Li2—O3—C8	164.6 (2)
Li2^iii—O5—Li1—O3^i	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)
Li2^iii—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)
Li2^iii—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)

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)