Poly[di-μ(2)-aqua-μ(2)-(5-methyl-pyrazine-2-carboxyl-ato)-(5-methyl-pyrazine-2-carboxyl-ato)-μ(3)-nitrato-trilithium].

The asymmetric unit of the title compound, [Li(3)(C(6)H(5)N(2)O(2))(2)(NO(3))(H(2)O)(2)](n) contains three Li(I) ions, two ligand anions, two water mol-ecules and a nitrate anion. Related by a centre of inversion, they form a centrosymmetric mol-ecular cluster in which one of the Li(I) ions shows trigonal-bipyramidal and the other two distorted tetra-hedral coordination. Li(I) ions are bridged by water O atoms and carboxyl-ate O atoms donated by one of the ligands. The clusters, bridged by two nitrato O atoms, form mol-ecular columns along [010], which are held together by O-H⋯O and O-H⋯N hydrogen bonds and π-π inter-actions [centroid-centroid distances = 3.694 (1) and 3.796 (1) Å].

Related literature

For the structure of a lithium complex with 3-amino­pyrazine-2-carboxyl­ate and aqua ligands, see: Starosta & Leciejewicz (2010 ▶). The structures of two complexes with pyridazine carboxyl­ate ligands have been also determined, see: Starosta & Leciejewicz (2011a ▶,b ▶). For the structure of a LiI complex with pyrimidine carboxyl­ate and nitrate ligands, see: Starosta & Leciejewicz (2011c ▶).

Experimental

Crystal data

[Li3(C6H5N2O2)2(NO3)(H2O)2]

M = 393.10

Monoclinic,

a = 13.0222 (1) Å

b = 7.2288 (1) Å

c = 18.5819 (2) Å

β = 100.760 (1)°

V = 1718.45 (3) Å3

Z = 4

Cu Kα radiation

μ = 1.10 mm−1

T = 293 K

0.23 × 0.20 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.672, T max = 1.000

15696 measured reflections

3215 independent reflections

2787 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.122

S = 1.07

3215 reflections

277 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024548/kp2334sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024548/kp2334Isup2.hkl

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

[Li3(C6H5N2O2)2(NO3)(H2O)2]	Z = 4
Mr = 393.10	F(000) = 808
Monoclinic, P21/c	Dx = 1.519 Mg m−3
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 13.0222 (1) Å	µ = 1.10 mm−1
b = 7.2288 (1) Å	T = 293 K
c = 18.5819 (2) Å	Plate, yellow
β = 100.760 (1)°	0.23 × 0.20 × 0.07 mm
V = 1718.45 (3) Å3

Oxford Diffraction Xcalibur Ruby diffractometer	3215 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2787 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 10.4922 pixels mm-1	θmax = 70.1°, θmin = 3.5°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −8→7
Tmin = 0.672, Tmax = 1.000	l = −22→22
15696 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0709P)2 + 0.484P] where P = (Fo2 + 2Fc2)/3
3215 reflections	(Δ/σ)max = 0.001
277 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. (CrysAlis PRO; Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Li1	0.90455 (19)	0.0331 (4)	1.03878 (13)	0.0379 (6)
Li2	0.7564 (2)	−0.2877 (4)	0.97211 (14)	0.0373 (6)
Li3	0.6256 (2)	0.0936 (5)	0.92945 (15)	0.0486 (7)
O31	0.47521 (9)	0.15187 (19)	0.91969 (6)	0.0482 (3)
O32	0.32570 (9)	0.1336 (2)	0.83857 (6)	0.0519 (4)
N31	0.58804 (10)	0.1142 (2)	0.81387 (7)	0.0371 (3)
C32	0.48413 (11)	0.1347 (2)	0.79451 (8)	0.0324 (3)
C33	0.43759 (12)	0.1538 (2)	0.72158 (8)	0.0392 (4)
H33	0.3653	0.1662	0.7095	0.047*
N32	0.49310 (11)	0.1548 (2)	0.66817 (7)	0.0419 (3)
C35	0.59618 (13)	0.1305 (2)	0.68670 (9)	0.0378 (4)
C36	0.64232 (12)	0.1096 (2)	0.76008 (9)	0.0407 (4)
H36	0.7142	0.0918	0.7720	0.049*
C37	0.42190 (12)	0.1403 (2)	0.85605 (8)	0.0357 (4)
C38	0.65821 (16)	0.1281 (3)	0.62641 (10)	0.0541 (5)
H38A	0.7279	0.0859	0.6454	0.081*
H38B	0.6609	0.2506	0.6070	0.081*
H38C	0.6256	0.0461	0.5882	0.081*
O12	1.20280 (8)	0.20920 (18)	1.11942 (6)	0.0430 (3)
O11	1.05909 (8)	0.09788 (18)	1.04975 (6)	0.0440 (3)
N11	0.95349 (10)	0.11349 (19)	1.15973 (7)	0.0353 (3)
N1	0.77531 (11)	0.3393 (2)	0.98615 (7)	0.0428 (4)
O1	0.76826 (9)	0.16678 (16)	0.98797 (6)	0.0457 (3)
O2	0.70264 (13)	0.4302 (2)	0.95323 (9)	0.0748 (5)
O3	0.85484 (14)	0.4171 (3)	1.01733 (9)	0.0840 (6)
O5	0.61725 (8)	−0.17265 (17)	0.96171 (6)	0.0378 (3)
H51	0.5869 (17)	−0.177 (3)	0.9989 (13)	0.057*
H52	0.5778 (18)	−0.236 (3)	0.9301 (13)	0.057*
O4	0.81382 (9)	−0.18568 (16)	1.06931 (5)	0.0335 (3)
C15	0.95823 (13)	0.1348 (2)	1.28881 (8)	0.0373 (4)
C12	1.05656 (11)	0.1468 (2)	1.17399 (7)	0.0295 (3)
C16	0.90570 (12)	0.1100 (2)	1.21690 (9)	0.0401 (4)
H16	0.8339	0.0900	1.2086	0.048*
C13	1.10941 (12)	0.1720 (2)	1.24494 (8)	0.0360 (4)
H13	1.1809	0.1954	1.2531	0.043*
C17	1.11144 (11)	0.1522 (2)	1.10905 (7)	0.0302 (3)
N12	1.06118 (11)	0.1639 (2)	1.30230 (7)	0.0402 (3)
C18	0.90366 (16)	0.1308 (3)	1.35290 (10)	0.0538 (5)
H18A	0.9461	0.0659	1.3928	0.081*
H18B	0.8377	0.0688	1.3393	0.081*
H18C	0.8922	0.2551	1.3678	0.081*
H42	0.8562 (17)	−0.250 (3)	1.0999 (12)	0.050 (5)*
H41	0.7640 (17)	−0.161 (3)	1.0912 (11)	0.048 (5)*

	U11	U22	U33	U12	U13	U23
Li1	0.0343 (12)	0.0511 (16)	0.0284 (11)	−0.0012 (11)	0.0061 (9)	−0.0045 (11)
Li2	0.0387 (13)	0.0443 (15)	0.0308 (12)	−0.0021 (11)	0.0115 (10)	−0.0018 (11)
Li3	0.0405 (14)	0.073 (2)	0.0317 (13)	0.0052 (14)	0.0061 (11)	0.0076 (13)
O31	0.0377 (6)	0.0820 (9)	0.0270 (5)	0.0121 (6)	0.0111 (4)	0.0055 (5)
O32	0.0318 (6)	0.0881 (10)	0.0383 (6)	0.0059 (6)	0.0127 (5)	0.0048 (6)
N31	0.0315 (6)	0.0520 (8)	0.0286 (6)	0.0081 (6)	0.0075 (5)	0.0056 (5)
C32	0.0307 (7)	0.0395 (8)	0.0280 (7)	0.0055 (6)	0.0078 (6)	0.0043 (6)
C33	0.0318 (8)	0.0559 (10)	0.0300 (7)	0.0047 (7)	0.0061 (6)	0.0059 (7)
N32	0.0425 (8)	0.0568 (9)	0.0271 (6)	0.0027 (6)	0.0081 (5)	0.0045 (6)
C35	0.0411 (8)	0.0423 (9)	0.0327 (7)	0.0025 (7)	0.0143 (6)	0.0017 (6)
C36	0.0311 (7)	0.0565 (10)	0.0366 (8)	0.0083 (7)	0.0120 (6)	0.0049 (7)
C37	0.0332 (8)	0.0464 (9)	0.0292 (7)	0.0086 (6)	0.0102 (6)	0.0063 (6)
C38	0.0568 (11)	0.0709 (13)	0.0409 (9)	0.0036 (9)	0.0256 (8)	0.0030 (9)
O12	0.0359 (6)	0.0620 (8)	0.0335 (5)	−0.0121 (5)	0.0123 (4)	−0.0051 (5)
O11	0.0376 (6)	0.0699 (8)	0.0255 (5)	−0.0032 (5)	0.0082 (4)	−0.0126 (5)
N11	0.0322 (6)	0.0450 (8)	0.0292 (6)	−0.0065 (5)	0.0065 (5)	−0.0037 (5)
N1	0.0540 (9)	0.0426 (8)	0.0383 (7)	0.0039 (7)	0.0255 (7)	0.0003 (6)
O1	0.0556 (7)	0.0316 (6)	0.0503 (7)	0.0030 (5)	0.0106 (6)	0.0020 (5)
O2	0.0892 (11)	0.0701 (10)	0.0720 (10)	0.0418 (9)	0.0327 (8)	0.0276 (8)
O3	0.0938 (12)	0.0904 (12)	0.0750 (11)	−0.0459 (10)	0.0344 (9)	−0.0309 (9)
O5	0.0318 (5)	0.0577 (7)	0.0245 (5)	0.0002 (5)	0.0069 (4)	−0.0042 (5)
O4	0.0312 (5)	0.0455 (6)	0.0240 (5)	0.0041 (5)	0.0054 (4)	0.0039 (4)
C15	0.0459 (9)	0.0362 (8)	0.0336 (8)	−0.0085 (7)	0.0173 (7)	−0.0046 (6)
C12	0.0309 (7)	0.0318 (7)	0.0262 (7)	−0.0033 (6)	0.0067 (6)	−0.0024 (5)
C16	0.0328 (8)	0.0505 (10)	0.0389 (8)	−0.0080 (7)	0.0121 (6)	−0.0050 (7)
C13	0.0337 (8)	0.0477 (9)	0.0271 (7)	−0.0078 (7)	0.0071 (6)	−0.0064 (6)
C17	0.0322 (7)	0.0344 (8)	0.0246 (6)	0.0009 (6)	0.0065 (5)	−0.0014 (5)
N12	0.0458 (8)	0.0499 (8)	0.0257 (6)	−0.0101 (6)	0.0090 (5)	−0.0059 (5)
C18	0.0676 (12)	0.0582 (11)	0.0439 (9)	−0.0142 (9)	0.0322 (9)	−0.0076 (8)

Li1—O11i	2.029 (3)	C38—H38A	0.9600
Li1—O11	2.039 (3)	C38—H38B	0.9600
Li1—O1	2.085 (3)	C38—H38C	0.9600
Li1—O4	2.114 (3)	O12—C17	1.2397 (18)
Li1—N11	2.293 (3)	O12—Li2i	1.958 (3)
Li1—Li1i	3.134 (5)	O11—C17	1.2460 (18)
Li2—O12i	1.958 (3)	O11—Li1i	2.029 (3)
Li2—O4	1.965 (3)	N11—C16	1.328 (2)
Li2—O5	1.970 (3)	N11—C12	1.3404 (19)
Li2—O2ii	2.163 (3)	N1—O2	1.219 (2)
Li2—O3ii	2.550 (4)	N1—O3	1.225 (2)
Li2—C17i	2.677 (3)	N1—O1	1.2516 (19)
Li2—N1ii	2.715 (3)	N1—Li2iii	2.715 (3)
Li2—H52	2.34 (2)	O2—Li2iii	2.163 (3)
Li3—O31	1.978 (3)	O3—Li2iii	2.550 (4)
Li3—O5	2.025 (4)	O5—H51	0.86 (2)
Li3—O1	2.039 (3)	O5—H52	0.84 (2)
Li3—N31	2.117 (3)	O4—H42	0.85 (2)
Li3—O2	2.637 (4)	O4—H41	0.85 (2)
O31—C37	1.2573 (19)	C15—N12	1.334 (2)
O32—C37	1.2351 (19)	C15—C16	1.394 (2)
N31—C36	1.328 (2)	C15—C18	1.497 (2)
N31—C32	1.3419 (19)	C12—C13	1.381 (2)
C32—C33	1.384 (2)	C12—C17	1.5134 (18)
C32—C37	1.5205 (19)	C16—H16	0.9300
C33—N32	1.332 (2)	C13—N12	1.336 (2)
C33—H33	0.9300	C13—H13	0.9300
N32—C35	1.334 (2)	C17—Li2i	2.677 (3)
C35—C36	1.392 (2)	C18—H18A	0.9600
C35—C38	1.498 (2)	C18—H18B	0.9600
C36—H36	0.9300	C18—H18C	0.9600
O11i—Li1—O11	79.21 (10)	N31—C36—H36	118.6
O11i—Li1—O1	99.02 (11)	C35—C36—H36	118.6
O11—Li1—O1	132.82 (15)	O32—C37—O31	127.21 (13)
O11i—Li1—O4	95.45 (12)	O32—C37—C32	117.25 (13)
O11—Li1—O4	137.34 (15)	O31—C37—C32	115.53 (13)
O1—Li1—O4	89.83 (11)	C35—C38—H38A	109.5
O11i—Li1—N11	148.03 (14)	C35—C38—H38B	109.5
O11—Li1—N11	75.84 (9)	H38A—C38—H38B	109.5
O1—Li1—N11	112.56 (12)	C35—C38—H38C	109.5
O4—Li1—N11	89.63 (10)	H38A—C38—H38C	109.5
O11i—Li1—Li1i	39.72 (7)	H38B—C38—H38C	109.5
O11—Li1—Li1i	39.50 (7)	C17—O12—Li2i	111.69 (12)
O1—Li1—Li1i	122.93 (15)	C17—O11—Li1i	133.79 (12)
O4—Li1—Li1i	122.68 (16)	C17—O11—Li1	121.84 (11)
N11—Li1—Li1i	112.96 (13)	Li1i—O11—Li1	100.79 (10)
O12i—Li2—O4	124.82 (15)	C16—N11—C12	116.54 (13)
O12i—Li2—O5	100.73 (13)	C16—N11—Li1	133.87 (12)
O4—Li2—O5	96.72 (12)	C12—N11—Li1	108.90 (11)
O12i—Li2—O2ii	105.34 (13)	O2—N1—O3	119.92 (19)
O4—Li2—O2ii	123.98 (14)	O2—N1—O1	119.79 (17)
O5—Li2—O2ii	96.79 (12)	O3—N1—O1	120.29 (17)
O12i—Li2—O3ii	109.12 (12)	O2—N1—Li2iii	50.83 (12)
O4—Li2—O3ii	85.96 (11)	O3—N1—Li2iii	69.11 (13)
O5—Li2—O3ii	141.47 (14)	O1—N1—Li2iii	170.49 (13)
O2ii—Li2—O3ii	52.56 (8)	N1—O1—Li3	107.95 (14)
O12i—Li2—C17i	25.49 (5)	N1—O1—Li1	114.41 (13)
O4—Li2—C17i	101.89 (11)	Li3—O1—Li1	137.29 (14)
O5—Li2—C17i	117.81 (13)	N1—O2—Li2iii	103.26 (16)
O2ii—Li2—C17i	118.44 (11)	N1—O2—Li3	79.75 (13)
O3ii—Li2—C17i	98.94 (10)	Li2iii—O2—Li3	176.60 (12)
O12i—Li2—N1ii	109.68 (12)	N1—O3—Li2iii	84.22 (14)
O4—Li2—N1ii	105.79 (12)	Li2—O5—Li3	109.33 (13)
O5—Li2—N1ii	119.60 (13)	Li2—O5—H51	117.3 (14)
O2ii—Li2—N1ii	25.90 (6)	Li3—O5—H51	109.4 (14)
O3ii—Li2—N1ii	26.66 (5)	Li2—O5—H52	105.8 (15)
C17i—Li2—N1ii	111.17 (10)	Li3—O5—H52	111.6 (15)
O12i—Li2—H52	94.5 (6)	H51—O5—H52	103 (2)
O4—Li2—H52	115.4 (6)	Li2—O4—Li1	99.79 (11)
O5—Li2—H52	20.1 (6)	Li2—O4—H42	119.7 (14)
O2ii—Li2—H52	80.0 (6)	Li1—O4—H42	105.3 (14)
O3ii—Li2—H52	130.7 (6)	Li2—O4—H41	109.1 (14)
C17i—Li2—H52	117.2 (6)	Li1—O4—H41	119.0 (14)
N1ii—Li2—H52	105.0 (6)	H42—O4—H41	104.7 (19)
O31—Li3—O5	97.02 (14)	N12—C15—C16	119.77 (13)
O31—Li3—O1	141.39 (18)	N12—C15—C18	117.61 (15)
O5—Li3—O1	100.53 (13)	C16—C15—C18	122.62 (15)
O31—Li3—N31	81.64 (11)	N11—C12—C13	120.98 (13)
O5—Li3—N31	110.61 (16)	N11—C12—C17	116.84 (12)
O1—Li3—N31	122.54 (15)	C13—C12—C17	122.18 (13)
O31—Li3—O2	99.10 (14)	N11—C16—C15	123.00 (14)
O5—Li3—O2	150.13 (14)	N11—C16—H16	118.5
O1—Li3—O2	52.51 (9)	C15—C16—H16	118.5
N31—Li3—O2	96.54 (13)	N12—C13—C12	122.10 (14)
C37—O31—Li3	115.81 (12)	N12—C13—H13	119.0
C36—N31—C32	116.92 (13)	C12—C13—H13	119.0
C36—N31—Li3	135.00 (13)	O12—C17—O11	126.37 (13)
C32—N31—Li3	108.08 (12)	O12—C17—C12	117.84 (12)
N31—C32—C33	120.58 (13)	O11—C17—C12	115.79 (13)
N31—C32—C37	116.98 (12)	O12—C17—Li2i	42.82 (9)
C33—C32—C37	122.43 (13)	O11—C17—Li2i	85.43 (10)
N32—C33—C32	122.04 (14)	C12—C17—Li2i	155.18 (12)
N32—C33—H33	119.0	C15—N12—C13	117.58 (13)
C32—C33—H33	119.0	C15—C18—H18A	109.5
C33—N32—C35	117.83 (13)	C15—C18—H18B	109.5
N32—C35—C36	119.78 (14)	H18A—C18—H18B	109.5
N32—C35—C38	117.75 (15)	C15—C18—H18C	109.5
C36—C35—C38	122.47 (15)	H18A—C18—H18C	109.5
N31—C36—C35	122.80 (14)	H18B—C18—H18C	109.5
O5—Li3—O31—C37	−97.15 (15)	O11i—Li1—O1—Li3	59.4 (2)
O1—Li3—O31—C37	146.2 (2)	O11—Li1—O1—Li3	142.98 (18)
N31—Li3—O31—C37	12.75 (18)	O4—Li1—O1—Li3	−36.13 (18)
O2—Li3—O31—C37	108.09 (15)	N11—Li1—O1—Li3	−125.66 (17)
O31—Li3—N31—C36	174.23 (18)	Li1i—Li1—O1—Li3	93.8 (2)
O5—Li3—N31—C36	−91.4 (2)	O3—N1—O2—Li2iii	−1.90 (17)
O1—Li3—N31—C36	26.8 (3)	O1—N1—O2—Li2iii	178.05 (12)
O2—Li3—N31—C36	75.9 (2)	O3—N1—O2—Li3	179.73 (15)
O31—Li3—N31—C32	−6.47 (16)	O1—N1—O2—Li3	−0.32 (13)
O5—Li3—N31—C32	87.93 (16)	Li2iii—N1—O2—Li3	−178.38 (12)
O1—Li3—N31—C32	−153.94 (18)	O31—Li3—O2—N1	151.21 (13)
O2—Li3—N31—C32	−104.75 (13)	O5—Li3—O2—N1	29.4 (3)
C36—N31—C32—C33	−1.3 (2)	O1—Li3—O2—N1	0.22 (9)
Li3—N31—C32—C33	179.29 (17)	N31—Li3—O2—N1	−126.25 (13)
C36—N31—C32—C37	−179.90 (15)	O31—Li3—O2—Li2iii	−1(2)
Li3—N31—C32—C37	0.65 (19)	O5—Li3—O2—Li2iii	−122.9 (18)
N31—C32—C33—N32	−0.8 (3)	O1—Li3—O2—Li2iii	−152.1 (19)
C37—C32—C33—N32	177.77 (15)	N31—Li3—O2—Li2iii	81.4 (19)
C32—C33—N32—C35	2.2 (3)	O2—N1—O3—Li2iii	1.58 (14)
C33—N32—C35—C36	−1.5 (2)	O1—N1—O3—Li2iii	−178.38 (13)
C33—N32—C35—C38	178.88 (17)	O12i—Li2—O5—Li3	−46.98 (16)
C32—N31—C36—C35	1.9 (3)	O4—Li2—O5—Li3	80.43 (14)
Li3—N31—C36—C35	−178.82 (18)	O2ii—Li2—O5—Li3	−154.06 (12)
N32—C35—C36—N31	−0.5 (3)	O3ii—Li2—O5—Li3	172.38 (19)
C38—C35—C36—N31	179.02 (17)	C17i—Li2—O5—Li3	−26.82 (17)
Li3—O31—C37—O32	164.44 (18)	N1ii—Li2—O5—Li3	−167.10 (12)
Li3—O31—C37—C32	−15.7 (2)	O31—Li3—O5—Li2	176.72 (12)
N31—C32—C37—O32	−170.32 (15)	O1—Li3—O5—Li2	−37.82 (15)
C33—C32—C37—O32	11.1 (2)	N31—Li3—O5—Li2	93.04 (15)
N31—C32—C37—O31	9.8 (2)	O2—Li3—O5—Li2	−61.0 (3)
C33—C32—C37—O31	−168.76 (16)	O12i—Li2—O4—Li1	7.0 (2)
O11i—Li1—O11—C17	−161.36 (16)	O5—Li2—O4—Li1	−101.06 (12)
O1—Li1—O11—C17	106.3 (2)	O2ii—Li2—O4—Li1	156.06 (15)
O4—Li1—O11—C17	−75.0 (2)	O3ii—Li2—O4—Li1	117.56 (10)
N11—Li1—O11—C17	−1.51 (16)	C17i—Li2—O4—Li1	19.27 (13)
Li1i—Li1—O11—C17	−161.36 (16)	N1ii—Li2—O4—Li1	135.57 (11)
O11i—Li1—O11—Li1i	0.0	O11i—Li1—O4—Li2	−32.20 (13)
O1—Li1—O11—Li1i	−92.35 (18)	O11—Li1—O4—Li2	−112.19 (19)
O4—Li1—O11—Li1i	86.3 (2)	O1—Li1—O4—Li2	66.84 (12)
N11—Li1—O11—Li1i	159.85 (14)	N11—Li1—O4—Li2	179.41 (11)
O11i—Li1—N11—C16	−134.3 (3)	Li1i—Li1—O4—Li2	−63.25 (18)
O11—Li1—N11—C16	−174.07 (17)	C16—N11—C12—C13	1.3 (2)
O1—Li1—N11—C16	55.1 (2)	Li1—N11—C12—C13	−170.60 (14)
O4—Li1—N11—C16	−34.6 (2)	C16—N11—C12—C17	−179.63 (14)
Li1i—Li1—N11—C16	−160.31 (17)	Li1—N11—C12—C17	8.50 (17)
O11i—Li1—N11—C12	35.6 (3)	C12—N11—C16—C15	−1.4 (2)
O11—Li1—N11—C12	−4.18 (14)	Li1—N11—C16—C15	167.87 (16)
O1—Li1—N11—C12	−135.04 (14)	N12—C15—C16—N11	0.1 (3)
O4—Li1—N11—C12	135.30 (12)	C18—C15—C16—N11	179.94 (16)
Li1i—Li1—N11—C12	9.6 (2)	N11—C12—C13—N12	0.3 (2)
O2—N1—O1—Li3	0.43 (18)	C17—C12—C13—N12	−178.79 (14)
O3—N1—O1—Li3	−179.62 (14)	Li2i—O12—C17—O11	19.9 (2)
Li2iii—N1—O1—Li3	9.6 (7)	Li2i—O12—C17—C12	−160.09 (13)
O2—N1—O1—Li1	174.88 (13)	Li1i—O11—C17—O12	32.3 (3)
O3—N1—O1—Li1	−5.17 (19)	Li1—O11—C17—O12	−173.52 (16)
Li2iii—N1—O1—Li1	−175.9 (6)	Li1i—O11—C17—C12	−147.73 (16)
O31—Li3—O1—N1	−50.3 (3)	Li1—O11—C17—C12	6.5 (2)
O5—Li3—O1—N1	−165.93 (12)	Li1i—O11—C17—Li2i	45.70 (19)
N31—Li3—O1—N1	71.2 (2)	Li1—O11—C17—Li2i	−160.08 (14)
O2—Li3—O1—N1	−0.22 (9)	N11—C12—C17—O12	169.59 (14)
O31—Li3—O1—Li1	137.1 (2)	C13—C12—C17—O12	−11.3 (2)
O5—Li3—O1—Li1	21.5 (2)	N11—C12—C17—O11	−10.4 (2)
N31—Li3—O1—Li1	−101.4 (2)	C13—C12—C17—O11	168.67 (15)
O2—Li3—O1—Li1	−172.75 (16)	N11—C12—C17—Li2i	136.1 (2)
O11i—Li1—O1—N1	−112.83 (13)	C13—C12—C17—Li2i	−44.8 (3)
O11—Li1—O1—N1	−29.2 (2)	C16—C15—N12—C13	1.5 (2)
O4—Li1—O1—N1	151.67 (11)	C18—C15—N12—C13	−178.41 (16)
N11—Li1—O1—N1	62.14 (16)	C12—C13—N12—C15	−1.7 (2)
Li1i—Li1—O1—N1	−78.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O32iv	0.85 (2)	1.92 (2)	2.7449 (15)	165.3 (19)
O4—H42···N12v	0.85 (2)	2.03 (2)	2.8414 (17)	159.0 (19)
O5—H52···N32vi	0.84 (2)	2.05 (2)	2.8550 (17)	162 (2)
O5—H51···O31iv	0.86 (2)	1.85 (2)	2.7055 (15)	172 (2)

Table 1

Selected bond lengths (Å)

Li1—O11i	2.029 (3)
Li1—O11	2.039 (3)
Li1—O1	2.085 (3)
Li1—O4	2.114 (3)
Li1—N11	2.293 (3)
Li2—O12i	1.958 (3)
Li2—O4	1.965 (3)
Li2—O5	1.970 (3)
Li2—O2ii	2.163 (3)
Li3—O31	1.978 (3)
Li3—O5	2.025 (4)
Li3—O1	2.039 (3)
Li3—N31	2.117 (3)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O32iii	0.85 (2)	1.92 (2)	2.7449 (15)	165.3 (19)
O4—H42⋯N12iv	0.85 (2)	2.03 (2)	2.8414 (17)	159.0 (19)
O5—H52⋯N32v	0.84 (2)	2.05 (2)	2.8550 (17)	162 (2)
O5—H51⋯O31iii	0.86 (2)	1.85 (2)	2.7055 (15)	172 (2)

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