catena-Poly[[(aqualithium)-μ-3-carboxypyrazine-2-carboxylato-κ4O2,N1:O3,N4] monohydrate]

Starosta, W.; Leciejewicz, J.

doi:10.1107/S160053681102887X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages m1133-m1134

doi:10.1107/S160053681102887X

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catena-Poly[[(aqualithium)-μ-3-carboxypyrazine-2-carboxylato-κ⁴O²,N¹:O³,N⁴] monohydrate]

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 11 July 2011; accepted 18 July 2011; online 23 July 2011)

The polymeric structure of the title compound {[Li(C₆H₃N₂O₄)(H₂O)]·H₂O}_n, contains two symmetry-independent Li^I complex units, both having distorted trigonal–bipyramidal coordination environments. The Li^I ions are bridged by both the N and O atoms of the ligands, generating two symmetry-independent polymeric chains propagating along the b-axis direction. In both ligands, the second carboxylato O atom remains protonated, serving as a donor in a short intramolecular O—H⋯O hydrogen bond. The coordination of each Li^I ion is completed by a water O atom. The ribbons are held together by a network of O—H⋯O hydrogen bonds in which the coordinated and uncoordinated water molecules are donors and the carboxylato O atoms act as acceptors.

Related literature

For the crystal structures of two Li^I complexes with a pyrazine-2,3-dicarboxylate ligand, see: Tombul et al. (2008 ); Tombul & Güven (2009 ). For the crystal structure of a Li^I complex with a pyrazine-2,3,5,6-tetracarboxylate ligand, see: Starosta & Leciejewicz (2010 ) and a pyrazine-2,5-dicarboxylate ligand, see: Starosta & Leciejewicz (2011 ). For the crystal structures of two structural forms of pyrazine-2,3-dicarboxylic acid dihydrate, see: Takusagawa & Shimada (1973 ); Premkumar et al. (2004 ). For the crystal structures of Zn complexes with a pyrazine-2,3-dicarboxylate ligand, see: Richard et al. (1974 ); Ptasiewicz-Bąk & Leciejewicz (1999 ); Gryz et al. (2005 ).

Experimental

Crystal data

[Li(C₆H₃N₂O₄)(H₂O)]·H₂O
M_r = 210.08
Monoclinic, P 2₁ /c
a = 12.673 (3) Å
b = 13.816 (3) Å
c = 10.956 (2) Å
β = 114.04 (3)°
V = 1752.0 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 293 K
0.32 × 0.14 × 0.09 mm

Data collection

Kuma KM4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.978, T_max = 0.984
3775 measured reflections
3595 independent reflections
1811 reflections with I > 2σ(I)
R_int = 0.064
3 standard reflections every 200 reflections intensity decay: 3.4%

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.149
S = 0.94
3595 reflections
311 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Selected bond lengths (Å)

Li1—O11	2.014 (5)
Li1—N11	2.117 (4)
Li1—O15	1.985 (6)
Li1—O14ⁱ	2.005 (5)
Li1—N12ⁱ	2.162 (4)
Li2—O21	2.003 (5)
Li2—N21	2.138 (4)
Li2—O25	2.016 (5)
Li2—O24ⁱⁱ	2.024 (5)
Li2—N22ⁱⁱ	2.162 (4)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H3⋯O24ⁱⁱ	0.83 (3)	2.12 (4)	2.943 (3)	170 (3)
O2—H4⋯O13ⁱⁱⁱ	0.93 (4)	1.93 (4)	2.841 (3)	169 (3)
O25—H251⋯O1ⁱⁱ	0.86 (3)	1.83 (4)	2.640 (3)	155 (3)
O25—H252⋯O21^iv	0.87 (4)	1.97 (4)	2.819 (3)	166 (3)
O15—H152⋯O25^v	0.97 (4)	1.93 (4)	2.837 (3)	154 (3)
O15—H151⋯O2^vi	0.72 (6)	2.11 (6)	2.816 (3)	165 (7)
O12—H131⋯O13	0.78 (6)	1.64 (6)	2.393 (3)	162 (7)
O23—H231⋯O22	0.67 (6)	1.76 (6)	2.416 (3)	170 (7)
O1—H1⋯O11	0.82 (3)	1.90 (3)	2.717 (3)	176 (3)
O1—H2⋯O22^vii	0.91 (4)	1.90 (4)	2.808 (3)	174 (3)
Symmetry codes: (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y, -z+1; (iv) -x+1, -y, -z+2; (v) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vi) x-1, y, z; (vii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: KM-4 Software (Kuma, 1996 $[Kuma (1996). KM-4 Software. Kuma Diffraction Ltd. Wrocław, Poland.]$ ); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 $[Kuma (2001). DATAPROC. Kuma Diffraction Ltd. Wrocław, Poland.]$ ); 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: 10.1107/S160053681102887X/kp2344sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102887X/kp2344Isup2.hkl

checkCIF report

Comment top

Pyrazine-2,3-dicarboxylate ligand shows a marked tendency to form metal coordination compounds depending on the conditions of chemical preparation. Three Zn^II coordination polymers with the title ligand (2,3-PZDC) showing polymeric structures are known: a triclinic complex Zn(2,3-PZDC)(H₂O)₂.H₂O (Richard et al., 1974); a monoclinic complex Zn(2,3-PZDC)(H₂O)₃. H₂O (Ptasiewicz-Bąk & Leciejewicz, 1999), and a monoclinic [(H₃O)¹⁺]₂ [Zn(2,3-PZDC)₂]^2- (Gryz, et al., 2005). Two Li^I complexes with the title ligand have been recently reported (Tombul et al., 2008; Tombul & Güven, 2009). The asymmetric unit of the title compound contains two symmetry independent Li^I ions, two ligand molecules, two coordinated and two crystal water molecules (Fig. 1, Table 1). Li^I ions and the ligands form two parallel molecular chains propagating in the b direction. In each, the Li ion shows a distorted trigonal bipyramidal coordination. The Li1 ion is 0.017 (1)Å out of the basal plane composed of carboxylato O11, O14ⁱ and aqua O15 atoms; hetero N11 and N12ⁱ atoms are at axial positions. The equatorial plane in the case of the Li2 ion consists of carboxylate O21, O24ⁱⁱ and water O25 atoms; hetero N21 and N22ⁱⁱ form the apices. The Li2 ion is 0.012 (1)Å out of the basal plane. The observed Li—O and Li—N bond distances are characteristic for Li^I complexes with diazine carboxylate ligands (Table 1). Each ligand uses both its N,O chelating sites to bridge Li^I ions. The second carboxylato O atoms do not participate in coordination but remain protonated to maintain the charge balance. In both ligands these protons are active in short intra-molecular hydrogen bonds of 2.393 (3) Å and 2.416 (3) Å (Table 2). The same effect has been also observed in another Li^I complex with the title ligand (Tombul et al., 2008), a complex with pyrazine-2,3,5,6-tetracarboxylate ligand (Starosta & Leciejewicz, 2010) and a complex with pyrazine -2,5-dicarboxylate ligand (Starosta & Leciejewicz, 2011). Bond lengths and bond angles within both pyrazine rings do not differ from those reported in the structures of two modifications of the parent acid (Takusagawa & Shimada, 1973; Premkumar, et al., 2004). Pyrazine rings are planar with r.m.s of 0.0040 (2) and 0.0094 (2) Å, for ligand 1 and 2, respectively. The carboxylate groups C17/O11/O12 and C8/O13/O14 make with the pyrazine ring 1 the dihedral angles of 4.8 (1)° and 3.8 (1)°, respectively. Dihedral angles made by the carboxylate groups C27/O21/O22 and C28/O23/O24 with the pyrazine ring 2 are 15.4 (2)° and 4.3 (1)°, respectively. Crystal and coordinated water molecules participate in a network of hydrogen bonds which connect the ribbons (Table 2, Fig. 2). They act as donors, the carboxylato O atoms as acceptors.

Related literature top

For the crystal structures of two Li^I complexes with a pyrazine-2,3-dicarboxylate ligand, see: Tombul et al. (2008); Tombul & Güven (2009). For the crystal structure of a Li^I complex with a pyrazine-2,3,5,6-tetracarboxylate ligand, see: Starosta & Leciejewicz (2010) and a pyrazine-2,5-dicarboxylate ligand, see: Starosta & Leciejewicz (2011). For the crystal structures of two structural forms of pyrazine-2,3-dicarboxylic acid dihydrate, see: Takusagawa & Shimada (1973); Premkumar et al. (2004). For the crystal structures of Zn(II) complexes with a pyrazine-2,3-dicarboxylate ligand, see: Richard et al. (1974); Ptasiewicz-Bąk & Leciejewicz (1999); Gryz et al. (2005).

Experimental top

A solution of 2 mmol s of LiOH in 50 mL of doubly distilled cold water was titrated with an aqueous solution of pyrazine-2,3-dicarboxylic acid dihydrate until the pH reached the value of 5.5. Then, the solution was boiled under reflux with stirring for 6 h. After cooling to room temperature the solution was left to crystallise. Polycrystalline material which was found after evaporation to dryness was repeatedly recrystallised from cold water until single-crystal plates appeared. They were washed with methanol and dried in air.

Computing details top

Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software (Kuma, 1996); data reduction: DATAPROC (Kuma, 2001); 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. Two structural units of the title compound with atom labelling scheme and 50% probability displacement ellipsoids. Symmetry code: (i) -x, y - 1/2,-z + 3/2; (ii) -x + 1, y + 1/2, -z + 3/2; (iii) -x + 1, y - 1/2, -z + 3/2; (iv) -x, y + 1/2, -z + 3/2.
	Fig. 2. Packing diagram of the structure viewed along the b axis.

catena-Poly[[(aqualithium)-µ-3-carboxypyrazine-2-carboxylato- κ⁴O²,N¹:O³,N⁴] monohydrate] top

Crystal data top

[Li(C₆H₃N₂O₄)(H₂O)]·H₂O	F(000) = 864
M_r = 210.08	D_x = 1.593 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.673 (3) Å	θ = 6–15°
b = 13.816 (3) Å	µ = 0.14 mm⁻¹
c = 10.956 (2) Å	T = 293 K
β = 114.04 (3)°	Plates, colourless
V = 1752.0 (6) Å³	0.32 × 0.14 × 0.09 mm
Z = 8

Data collection top

Kuma KM4 four-circle diffractometer	1811 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.064
Graphite monochromator	θ_max = 27.7°, θ_min = 1.8°
profile data from ω/2θ scans	h = 0→14
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = −18→0
T_min = 0.978, T_max = 0.984	l = −13→13
3775 measured reflections	3 standard reflections every 200 reflections
3595 independent reflections	intensity decay: 3.4%

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0987P)²] where P = (F_o² + 2F_c²)/3
3595 reflections	(Δ/σ)_max < 0.001
311 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Li(C₆H₃N₂O₄)(H₂O)]·H₂O	V = 1752.0 (6) Å³
M_r = 210.08	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.673 (3) Å	µ = 0.14 mm⁻¹
b = 13.816 (3) Å	T = 293 K
c = 10.956 (2) Å	0.32 × 0.14 × 0.09 mm
β = 114.04 (3)°

Data collection top

Kuma KM4 four-circle diffractometer	1811 reflections with I > 2σ(I)
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	R_int = 0.064
T_min = 0.978, T_max = 0.984	3 standard reflections every 200 reflections
3775 measured reflections	intensity decay: 3.4%
3595 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.28 e Å⁻³
3595 reflections	Δρ_min = −0.36 e Å⁻³
311 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
N11	−0.01503 (17)	0.17705 (13)	0.7604 (2)	0.0323 (5)
N12	0.00129 (18)	−0.02194 (13)	0.7752 (2)	0.0325 (5)
O14	0.1043 (2)	−0.12689 (12)	0.6604 (2)	0.0553 (6)
C13	0.0533 (2)	0.02779 (15)	0.7099 (2)	0.0283 (5)
O13	0.17126 (19)	−0.00377 (13)	0.5878 (2)	0.0544 (6)
O11	0.07742 (16)	0.28612 (11)	0.6413 (2)	0.0462 (5)
O12	0.1688 (2)	0.16941 (14)	0.5894 (2)	0.0540 (6)
C17	0.1009 (2)	0.19946 (16)	0.6398 (3)	0.0351 (6)
C12	0.0454 (2)	0.12986 (15)	0.7036 (2)	0.0282 (5)
C18	0.1147 (2)	−0.03926 (17)	0.6484 (3)	0.0354 (6)
C15	−0.0584 (2)	0.02637 (18)	0.8300 (3)	0.0376 (6)
H15	−0.0953	−0.0075	0.8747	0.045*
C16	−0.0671 (2)	0.12673 (18)	0.8224 (3)	0.0372 (6)
H16	−0.1101	0.1588	0.8614	0.045*
O21	0.41371 (16)	0.10101 (11)	0.8670 (2)	0.0406 (5)
N22	0.51761 (17)	0.40335 (13)	0.7446 (2)	0.0318 (5)
O24	0.39022 (18)	0.51517 (11)	0.8178 (2)	0.0496 (6)
O22	0.33218 (18)	0.22600 (12)	0.9203 (2)	0.0523 (6)
N21	0.53363 (18)	0.20579 (13)	0.7753 (2)	0.0345 (5)
O23	0.3238 (2)	0.40041 (15)	0.9029 (3)	0.0603 (7)
C28	0.3850 (2)	0.42871 (16)	0.8427 (3)	0.0374 (6)
C22	0.4624 (2)	0.25575 (15)	0.8148 (2)	0.0271 (5)
C23	0.4556 (2)	0.35762 (14)	0.8001 (2)	0.0271 (5)
C27	0.3966 (2)	0.18992 (16)	0.8712 (3)	0.0324 (6)
C26	0.5974 (2)	0.25337 (17)	0.7252 (3)	0.0404 (7)
H26	0.6494	0.2196	0.7009	0.048*
C25	0.5878 (2)	0.35298 (17)	0.7085 (3)	0.0383 (6)
H25	0.6321	0.3847	0.6708	0.046*
Li2	0.5322 (4)	0.0529 (3)	0.8042 (4)	0.0371 (10)
O25	0.66173 (18)	0.02579 (12)	0.9834 (2)	0.0389 (5)
O1	0.2117 (2)	0.38123 (13)	0.5402 (2)	0.0502 (6)
O15	−0.1887 (2)	0.31162 (16)	0.5473 (2)	0.0532 (6)
Li1	−0.0422 (4)	0.3254 (3)	0.7089 (5)	0.0416 (10)
O2	0.71760 (19)	0.12508 (13)	0.5331 (2)	0.0459 (5)
H3	0.695 (3)	0.092 (2)	0.581 (3)	0.043 (9)*
H4	0.754 (3)	0.092 (3)	0.488 (4)	0.080 (12)*
H251	0.707 (3)	−0.009 (2)	0.961 (3)	0.055 (9)*
H252	0.633 (3)	−0.004 (3)	1.033 (3)	0.064 (11)*
H152	−0.252 (3)	0.355 (3)	0.538 (4)	0.083 (12)*
H151	−0.223 (5)	0.268 (5)	0.534 (7)	0.15 (3)*
H131	0.183 (5)	0.115 (4)	0.590 (6)	0.15 (2)*
H231	0.329 (5)	0.353 (4)	0.916 (5)	0.12 (2)*
H1	0.169 (2)	0.354 (2)	0.568 (3)	0.032 (8)*
H2	0.248 (3)	0.342 (3)	0.501 (4)	0.079 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0411 (12)	0.0160 (9)	0.0441 (12)	0.0021 (8)	0.0218 (10)	0.0018 (8)
N12	0.0398 (11)	0.0159 (9)	0.0466 (13)	0.0001 (8)	0.0227 (10)	0.0039 (8)
O14	0.0881 (15)	0.0120 (8)	0.0887 (16)	−0.0007 (9)	0.0594 (13)	−0.0029 (9)
C13	0.0363 (13)	0.0097 (10)	0.0397 (13)	0.0019 (9)	0.0163 (11)	0.0003 (9)
O13	0.0865 (15)	0.0181 (9)	0.0901 (16)	0.0039 (9)	0.0680 (14)	0.0005 (9)
O11	0.0621 (12)	0.0096 (8)	0.0848 (15)	0.0024 (8)	0.0482 (12)	0.0064 (8)
O12	0.0775 (15)	0.0164 (9)	0.0968 (17)	0.0029 (9)	0.0648 (14)	0.0060 (10)
C17	0.0456 (14)	0.0131 (10)	0.0541 (17)	0.0001 (10)	0.0279 (13)	0.0036 (10)
C12	0.0354 (13)	0.0127 (10)	0.0380 (13)	0.0035 (9)	0.0164 (11)	0.0023 (9)
C18	0.0506 (16)	0.0155 (11)	0.0486 (15)	0.0026 (10)	0.0288 (13)	−0.0020 (10)
C15	0.0490 (15)	0.0209 (12)	0.0519 (16)	0.0001 (11)	0.0298 (13)	0.0058 (11)
C16	0.0474 (15)	0.0234 (12)	0.0483 (15)	0.0073 (11)	0.0272 (13)	0.0054 (11)
O21	0.0552 (11)	0.0099 (7)	0.0693 (13)	0.0023 (7)	0.0383 (10)	0.0053 (7)
N22	0.0382 (12)	0.0162 (9)	0.0433 (12)	0.0031 (8)	0.0187 (10)	0.0052 (8)
O24	0.0805 (14)	0.0101 (8)	0.0791 (15)	0.0036 (8)	0.0538 (12)	0.0022 (8)
O22	0.0747 (14)	0.0180 (8)	0.0953 (16)	0.0062 (9)	0.0666 (13)	0.0091 (9)
N21	0.0464 (12)	0.0153 (9)	0.0504 (13)	0.0069 (9)	0.0286 (11)	0.0053 (9)
O23	0.0965 (19)	0.0157 (9)	0.1049 (19)	0.0075 (10)	0.0781 (16)	0.0063 (10)
C28	0.0554 (17)	0.0122 (10)	0.0566 (17)	0.0037 (10)	0.0352 (14)	0.0018 (10)
C22	0.0348 (13)	0.0119 (10)	0.0377 (14)	0.0031 (9)	0.0182 (11)	0.0038 (9)
C23	0.0343 (12)	0.0112 (10)	0.0388 (14)	0.0022 (9)	0.0179 (11)	0.0020 (9)
C27	0.0399 (14)	0.0161 (10)	0.0458 (15)	0.0021 (10)	0.0223 (12)	0.0058 (10)
C26	0.0515 (16)	0.0216 (12)	0.0630 (18)	0.0098 (11)	0.0386 (15)	0.0085 (11)
C25	0.0473 (15)	0.0238 (13)	0.0537 (17)	0.0024 (11)	0.0307 (14)	0.0100 (11)
Li2	0.052 (3)	0.0131 (17)	0.053 (3)	0.0028 (17)	0.028 (2)	0.0018 (17)
O25	0.0508 (12)	0.0159 (8)	0.0592 (13)	0.0004 (8)	0.0319 (10)	−0.0022 (8)
O1	0.0647 (14)	0.0193 (9)	0.0889 (17)	−0.0108 (9)	0.0540 (13)	−0.0094 (10)
O15	0.0506 (13)	0.0231 (10)	0.0787 (16)	0.0043 (10)	0.0190 (11)	0.0035 (10)
Li1	0.056 (3)	0.0126 (19)	0.065 (3)	0.0019 (17)	0.033 (2)	0.0019 (18)
O2	0.0672 (14)	0.0219 (9)	0.0581 (13)	−0.0051 (9)	0.0351 (12)	−0.0045 (9)

Geometric parameters (Å, º) top

N11—C16	1.321 (3)	O24—C28	1.233 (3)
N11—C12	1.337 (3)	Li2—O24ⁱⁱ	2.024 (5)
Li1—O11	2.014 (5)	O22—C27	1.250 (3)
Li1—N11	2.117 (4)	N21—C26	1.322 (3)
Li1—O15	1.985 (6)	N21—C22	1.340 (3)
Li1—O14ⁱ	2.005 (5)	O23—C28	1.267 (3)
Li1—N12ⁱ	2.162 (4)	O23—H231	0.67 (6)
N12—C15	1.322 (3)	C28—C23	1.524 (3)
N12—C13	1.342 (3)	C22—C23	1.415 (3)
Li1—N12ⁱ	2.162 (4)	C22—C27	1.525 (3)
O14—C18	1.231 (3)	C26—C25	1.387 (3)
Li1—O14ⁱ	2.005 (5)	C26—H26	0.9300
C13—C12	1.413 (3)	C25—H25	0.9300
C13—C18	1.531 (3)	Li2—O21	2.003 (5)
O13—C18	1.258 (3)	Li2—N21	2.138 (4)
O11—C17	1.235 (3)	Li2—O25	2.016 (5)
O12—C17	1.267 (3)	Li2—O24ⁱⁱ	2.024 (5)
O12—H131	0.78 (6)	Li2—N22ⁱⁱ	2.162 (4)
C17—C12	1.519 (3)	O25—H251	0.86 (3)
C15—C16	1.391 (3)	O25—H252	0.87 (4)
C15—H15	0.9300	O1—H1	0.82 (3)
C16—H16	0.9300	O1—H2	0.91 (4)
O21—C27	1.251 (3)	O15—H152	0.97 (4)
N22—C25	1.312 (3)	O15—H151	0.72 (6)
N22—C23	1.333 (3)	O2—H3	0.83 (3)
Li2—N22ⁱⁱ	2.162 (4)	O2—H4	0.93 (4)

C16—N11—C12	118.9 (2)	C23—C22—C27	128.4 (2)
C16—N11—Li1	125.8 (2)	N22—C23—C22	120.2 (2)
C12—N11—Li1	114.20 (19)	N22—C23—C28	111.30 (18)
C15—N12—C13	118.65 (19)	C22—C23—C28	128.5 (2)
C15—N12—Li1ⁱⁱⁱ	128.2 (2)	O22—C27—O21	124.1 (2)
C13—N12—Li1ⁱⁱⁱ	112.88 (19)	O22—C27—C22	119.8 (2)
C18—O14—Li1ⁱⁱⁱ	119.3 (2)	O21—C27—C22	116.0 (2)
N12—C13—C12	119.8 (2)	N21—C26—C25	120.8 (2)
N12—C13—C18	111.86 (18)	N21—C26—H26	119.6
C12—C13—C18	128.4 (2)	C25—C26—H26	119.6
C17—O11—Li1	119.2 (2)	N22—C25—C26	121.3 (2)
C17—O12—H131	121 (5)	N22—C25—H25	119.3
O11—C17—O12	122.2 (2)	C26—C25—H25	119.3
O11—C17—C12	116.6 (2)	O21—Li2—O25	98.9 (2)
O12—C17—C12	121.1 (2)	O21—Li2—O24ⁱⁱ	161.1 (3)
N11—C12—C13	120.4 (2)	O25—Li2—O24ⁱⁱ	100.0 (2)
N11—C12—C17	111.46 (18)	O21—Li2—N21	77.02 (15)
C13—C12—C17	128.1 (2)	O25—Li2—N21	106.0 (2)
O14—C18—O13	123.3 (2)	O24ⁱⁱ—Li2—N21	96.94 (19)
O14—C18—C13	116.9 (2)	O21—Li2—N22ⁱⁱ	102.6 (2)
O13—C18—C13	119.8 (2)	O25—Li2—N22ⁱⁱ	95.94 (17)
N12—C15—C16	121.5 (2)	O24ⁱⁱ—Li2—N22ⁱⁱ	76.26 (15)
N12—C15—H15	119.3	N21—Li2—N22ⁱⁱ	157.9 (3)
C16—C15—H15	119.3	Li2—O25—H251	101 (2)
N11—C16—C15	120.7 (2)	Li2—O25—H252	108 (2)
N11—C16—H16	119.6	H251—O25—H252	114 (3)
C15—C16—H16	119.6	H1—O1—H2	116 (3)
C27—O21—Li2	120.3 (2)	Li1—O15—H152	118 (2)
C25—N22—C23	119.0 (2)	Li1—O15—H151	122 (5)
C25—N22—Li2^iv	126.7 (2)	H152—O15—H151	96 (5)
C23—N22—Li2^iv	113.48 (19)	O15—Li1—O14ⁱ	99.9 (2)
C28—O24—Li2^iv	118.7 (2)	O15—Li1—O11	102.5 (2)
C26—N21—C22	118.94 (19)	O14ⁱ—Li1—O11	157.6 (3)
C26—N21—Li2	126.6 (2)	O15—Li1—N11	97.8 (2)
C22—N21—Li2	114.44 (19)	O14ⁱ—Li1—N11	101.3 (2)
C28—O23—H231	113 (5)	O11—Li1—N11	76.82 (16)
O24—C28—O23	120.9 (2)	O15—Li1—N12ⁱ	105.8 (2)
O24—C28—C23	117.7 (2)	O14ⁱ—Li1—N12ⁱ	76.87 (16)
O23—C28—C23	121.3 (2)	O11—Li1—N12ⁱ	95.81 (19)
N21—C22—C23	119.6 (2)	N11—Li1—N12ⁱ	156.3 (3)
N21—C22—C27	112.03 (19)	H3—O2—H4	116 (3)

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x, y−1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H3···O24ⁱⁱ	0.83 (3)	2.12 (4)	2.943 (3)	170 (3)
O2—H4···O13^v	0.93 (4)	1.93 (4)	2.841 (3)	169 (3)
O25—H251···O1ⁱⁱ	0.86 (3)	1.83 (4)	2.640 (3)	155 (3)
O25—H252···O21^vi	0.87 (4)	1.97 (4)	2.819 (3)	166 (3)
O15—H152···O25^vii	0.97 (4)	1.93 (4)	2.837 (3)	154 (3)
O15—H151···O2^viii	0.72 (6)	2.11 (6)	2.816 (3)	165 (7)
O12—H131···O13	0.78 (6)	1.64 (6)	2.393 (3)	162 (7)
O23—H231···O22	0.67 (6)	1.76 (6)	2.416 (3)	170 (7)
O1—H1···O11	0.82 (3)	1.90 (3)	2.717 (3)	176 (3)
O1—H2···O22^ix	0.91 (4)	1.90 (4)	2.808 (3)	174 (3)

Symmetry codes: (ii) −x+1, y−1/2, −z+3/2; (v) −x+1, −y, −z+1; (vi) −x+1, −y, −z+2; (vii) x−1, −y+1/2, z−1/2; (viii) x−1, y, z; (ix) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Li(C₆H₃N₂O₄)(H₂O)]·H₂O
M_r	210.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.673 (3), 13.816 (3), 10.956 (2)
β (°)	114.04 (3)
V (Å³)	1752.0 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.32 × 0.14 × 0.09

Data collection
Diffractometer	Kuma KM4 four-circle diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.978, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	3775, 3595, 1811
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.149, 0.94
No. of reflections	3595
No. of parameters	311
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.36

Computer programs: KM-4 Software (Kuma, 1996), DATAPROC (Kuma, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Li1—O11	2.014 (5)	Li2—O21	2.003 (5)
Li1—N11	2.117 (4)	Li2—N21	2.138 (4)
Li1—O15	1.985 (6)	Li2—O25	2.016 (5)
Li1—O14ⁱ	2.005 (5)	Li2—O24ⁱⁱ	2.024 (5)
Li1—N12ⁱ	2.162 (4)	Li2—N22ⁱⁱ	2.162 (4)

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H3···O24ⁱⁱ	0.83 (3)	2.12 (4)	2.943 (3)	170 (3)
O2—H4···O13ⁱⁱⁱ	0.93 (4)	1.93 (4)	2.841 (3)	169 (3)
O25—H251···O1ⁱⁱ	0.86 (3)	1.83 (4)	2.640 (3)	155 (3)
O25—H252···O21^iv	0.87 (4)	1.97 (4)	2.819 (3)	166 (3)
O15—H152···O25^v	0.97 (4)	1.93 (4)	2.837 (3)	154 (3)
O15—H151···O2^vi	0.72 (6)	2.11 (6)	2.816 (3)	165 (7)
O12—H131···O13	0.78 (6)	1.64 (6)	2.393 (3)	162 (7)
O23—H231···O22	0.67 (6)	1.76 (6)	2.416 (3)	170 (7)
O1—H1···O11	0.82 (3)	1.90 (3)	2.717 (3)	176 (3)
O1—H2···O22^vii	0.91 (4)	1.90 (4)	2.808 (3)	174 (3)

Symmetry codes: (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y, −z+1; (iv) −x+1, −y, −z+2; (v) x−1, −y+1/2, z−1/2; (vi) x−1, y, z; (vii) x, −y+1/2, z−1/2.

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