catena-Poly[[(3,5-dicarb­oxy­pyrazine-2,6-dicarboxyl­ato-κ3O2,N1,O6)lithium(I)]-μ-aqua-[triaqua­lithium(I)]-μ-aqua]

Starosta, W.; Leciejewicz, J.

doi:10.1107/S1600536810045903

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1561-m1562

https://doi.org/10.1107/S1600536810045903

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catena-Poly[[(3,5-dicarboxypyrazine-2,6-dicarboxylato-κ³O²,N¹,O⁶)lithium(I)]-μ-aqua-[triaqualithium(I)]-μ-aqua]

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 27 October 2010; accepted 8 November 2010; online 13 November 2010)

The title coordination polymer, [Li₂(C₈H₂N₂O₈)(H₂O)₅]_n contains two symmetry-independent Li⁺ ions; one is coordinated by five water O atoms, the other by an O,N,O′-tridentate doubly deprotonated pyrazine-2,3,5,6-tetracarboxylate ligand and two water O atoms. Water molecules bridge adjacent Li⁺ ions into ribbons propagating in [100]; an alternative analysis of the structure considers it to contain alternating [Li(C₈H₂N₂O₈)(H₂O)₂]⁻ anions and [Li(H₂O)₃]⁺ cations. In the polymeric model, both lithium ions show distorted trigonal–bipyramidal coordination geometries. Within the ligand, the carboxyl H atoms participate in short, almost symmetric O⋯H⋯O hydrogen bonds in which the non-coordinated carboxylate O atoms are donors and acceptors. In the crystal, the ribbons interact via a network of O—H⋯O hydrogen bonds in which the coordinated water molecules act as donors and ligand carboxylate O atoms as acceptors.

Related literature

For the crystal structures of 3d transition metal complexes with pyrazine-2,3,5,6-tetracarboxylate and water ligands, see: Alfonso et al. (2001 ); Graf et al. (1993 ); Marioni et al. (1986 ); Marioni et al. (1994 ). For the structure of a Ca(II) complex, see: Starosta & Leciejewicz (2008 ). For the structure of a Li complex with pyrazine-2,3-dicarboxylate and water ligands, see: Tombul et al. (2008 ). For a review on metal organic frameworks (MOFs), see: MacGillivray (2010 ).

Experimental

Crystal data

[Li₂(C₈H₂N₂O₈)(H₂O)₅]
M_r = 358.08
Monoclinic, P 2₁ /m
a = 6.8806 (14) Å
b = 11.767 (2) Å
c = 8.8082 (18) Å
β = 103.59 (3)°
V = 693.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.17 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008) $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England]$ T_min = 0.971, T_max = 0.975
2291 measured reflections
2136 independent reflections
1459 reflections with I > 2σ(I)
R_int = 0.012
3 standard reflections every 200 reflections intensity decay: 0.5%

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.127
S = 1.03
2136 reflections
148 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected bond lengths (Å)

Li1—N1	2.119 (4)
Li1—O4	2.1194 (13)
Li1—O8	1.997 (4)
Li1—O7	2.075 (5)
Li1—O4ⁱ	2.1194 (13)
Li2—O6	1.9412 (12)
Li2—O7	2.385 (4)
Li2—O5	2.052 (4)
Li2—O6ⁱ	1.9412 (12)
Li2—O8ⁱⁱ	2.067 (4)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z]$ ; (ii) x-1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H61⋯O2ⁱⁱⁱ	0.90 (2)	1.87 (2)	2.7597 (14)	165.4 (19)
O6—H62⋯O4^iv	0.91 (3)	1.91 (3)	2.8129 (14)	173 (2)
O8—H81⋯O2^v	0.86 (2)	1.92 (2)	2.7753 (13)	175.9 (19)
O7—H71⋯O3^iv	0.862 (19)	2.037 (19)	2.8950 (12)	173.8 (17)
O5—H51⋯O1ⁱⁱⁱ	0.903 (19)	2.010 (19)	2.9110 (13)	175.4 (17)
O1—H32⋯O3	1.19 (2)	1.21 (2)	2.3894 (15)	173 (2)
Symmetry codes: (iii) -x, -y+2, -z+1; (iv) -x+1, -y+2, -z+2; (v) x+1, y, z+1.

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: https://doi.org/10.1107/S1600536810045903/hb5710sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045903/hb5710Isup2.hkl

checkCIF report

Comment top

Multidentate organic acids are widely used as ligands in a search for coordination polymers which can find applications in such fields as hydrogen or carbon dioxide storage, catalysis and ion-exchange resins (MacGillivray, 2010). Pyrazine-2,3,5,6-tetracarboxylate ligand is a promising building block in constructing metal-organic frameworks, since it exhibits ten chelating sites: two hetero-ring N atoms and four potentially bidentate carboxylate groups. A formation of a variety of catenated and layered polymeric structures has been reported in compounds of 3 transition metal ions with the title ligand (Marioni et al., 1986; Graf et al., 1993; Marioni et al., 1994; Alfonso et al., 2001). The Ca(II) complex shows a three-dimensional polymeric structure (Starosta & Leciejewicz, 2008). The asymmetric unit cell of a Li(I) complex with the title ligand contains two symmetry independent Li1 and Li2 ions positioned on a mirror plane with y=3/4. Pyrazine-ring N1 and N2 atoms and coordinated water O5, O7, O8 atoms are also positioned on this plane (Fig.1). The Li1 ion is chelated by the N1, O4, O4ⁱ ligand bonding moiety with typical Li—N and Li—O bond distances of 2.119 (4)Å and 2.119 (1) Å, respectively and two bridging aqua O7 and O8 atoms (d_Li1—O7 =2.075 (5)° and d_Li1—O8=1.997 (4) Å). The O4 and O4ⁱ atoms are at opposite apices of a distorted trigonal bipyramid; its equatorial plane is composed of coplanar Li1 ion, hetero-ring N1 atom and the bridging O7 and O8 atoms. Pyrazine-ring atoms are coplanar with r.m.s. of 0.0009 (1) Å; their plane makes an angle of 90° with the equatorial plane. Carboxylic groups C6/O1/O2 and C5/O1/O2 make angles with pyrazine ring of 1.45 (13)° and 4.69 (14)°, respectively. Bond distances and bond angles within the ligand molecule do not differ from those observed in other complexes with the title ligand. A proton situated between carboxylate O3 and O1 atoms, clearly visible on the Fourier map, forms a symmetrical intra-molecular hydrogen bond of 2.389 (2)Å and O3—H32—O1 angle of 173 (3)°. The (2-) charge of the ligand is compensated by the (1+) charge of the Li1 ion. The resulting anion has a charge of (1-). On the other hand, the Li2 ion as coordinated only by aqua O atoms, retains its charge of (1+). The ribbons (Fig. 2) are built of Li(C₈H₂N₂O₈)(H₂O)₂]^1- anions and [Li(H₂O)₄]¹⁺cations bridged by aqua O7 and O8 atoms belonging to coordination spheres of both Li ions. The bridging pathway propagates with Li1—O7—Li2 angle of 111.19 (14)° and Li1—O8—Li2ⁱⁱⁱ angle of 103.81 (16)°. The coordination environment of the Li2 ion is composed of five aqua O atoms, two of them O7 and O8 are bridging it with the Li1 ions. The Li2 ion, O5, O7 and O8 atoms are coplanar and form an equatorial plane of a distorted trigonal bipyramid with O6 and O6ⁱ atoms at opposite apices. Li—O bond distances within this coordination polyhedron are in the range from 1.941 (1)Å to 2.067 (4) Å, the Li2—O7 bridging bond distance amounts to 2.385 (4) Å. Trigonal bipyramidal coordination geometry of a Li(I) ion has been also observed in the structure of its complex with pyrazine-2,3-dicarboxylate and water ligands (Tombul et al. 2008). Coordinated water O atoms are donors in a network of hydrogen bonds to carboxylate O atoms in adjacent ribbons which act as acceptors.

Related literature top

For the crystal structures of 3d transition metal complexes with pyrazine-2,3,5,6-tetracarboxylate and water ligands, see: Alfonso et al. (2001); Graf et al. (1993); Marioni et al. (1986); Marioni et al. (1994). For the structure of a Ca(II) complex, see: Starosta & Leciejewicz (2008). For the structure of a Li complex with pyrazine-2,3- dicarboxylate and water ligands, see: Tombul et al. (2008). For a review on MOFs, see: MacGillivray (2010).

Experimental top

50 ml of aqueous solution containing 1 mmol of pyrazine-2,3,5,6-tetracarboxylic acid was added to 50 ml of an aqueous solution containing 4 mmol of lithium hydroxide. The mixture was boiled under reflux for 3 h with conatant stirring, then left to crystallize at room temperature. After a couple of days crystals of (1) were found in the form of colourless blocks. They were dissolved in water and recrystallized three times. The final crystals were washed in metanol and dried in the air.

Structure description top

For the crystal structures of 3d transition metal complexes with pyrazine-2,3,5,6-tetracarboxylate and water ligands, see: Alfonso et al. (2001); Graf et al. (1993); Marioni et al. (1986); Marioni et al. (1994). For the structure of a Ca(II) complex, see: Starosta & Leciejewicz (2008). For the structure of a Li complex with pyrazine-2,3- dicarboxylate and water ligands, see: Tombul et al. (2008). For a review on MOFs, see: MacGillivray (2010).

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. A structural unit of (1) with atom labelling scheme and 50% probability displacement ellipsoids. Symmetry code: (i) x, -y + 3/2, z; (ii) X+1, y, z; (iii) x - 1, y, z.
	Fig. 2. Packing diagram of the structure.

catena-Poly[[(3,5-dicarboxypyrazine-2,6-dicarboxylato- κ³O²,N¹,O⁶)lithium(I)]-µ-aqua- [triaqualithium(I)]-µ-aqua] top

Crystal data top

[Li₂(C₈H₂N₂O₈)(H₂O)₅]	F(000) = 368
M_r = 358.08	D_x = 1.716 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
a = 6.8806 (14) Å	Cell parameters from 25 reflections
b = 11.767 (2) Å	θ = 6–15°
c = 8.8082 (18) Å	µ = 0.16 mm⁻¹
β = 103.59 (3)°	T = 293 K
V = 693.2 (2) Å³	Blocks, colourless
Z = 2	0.23 × 0.21 × 0.17 mm

Data collection top

Kuma KM-4 four-circle diffractometer	1459 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.012
Graphite monochromator	θ_max = 30.1°, θ_min = 2.4°
profile data from ω/2θ scans	h = 0→9
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = 0→16
T_min = 0.971, T_max = 0.975	l = −12→12
2291 measured reflections	3 standard reflections every 200 reflections
2136 independent reflections	intensity decay: 0.5%

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0886P)² + 0.040P] where P = (F_o² + 2F_c²)/3
2136 reflections	(Δ/σ)_max < 0.001
148 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Li₂(C₈H₂N₂O₈)(H₂O)₅]	V = 693.2 (2) Å³
M_r = 358.08	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 6.8806 (14) Å	µ = 0.16 mm⁻¹
b = 11.767 (2) Å	T = 293 K
c = 8.8082 (18) Å	0.23 × 0.21 × 0.17 mm
β = 103.59 (3)°

Data collection top

Kuma KM-4 four-circle diffractometer	1459 reflections with I > 2σ(I)
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	R_int = 0.012
T_min = 0.971, T_max = 0.975	3 standard reflections every 200 reflections
2291 measured reflections	intensity decay: 0.5%
2136 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.42 e Å⁻³
2136 reflections	Δρ_min = −0.32 e Å⁻³
148 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
N1	0.4556 (2)	0.7500	0.72520 (15)	0.0184 (3)
N2	0.1994 (2)	0.7500	0.44032 (15)	0.0197 (3)
O4	0.61711 (14)	0.92277 (7)	0.87982 (11)	0.0287 (2)
O2	0.06363 (16)	0.93417 (8)	0.28320 (11)	0.0354 (3)
O1	0.21919 (16)	1.05057 (7)	0.46536 (10)	0.0315 (3)
O3	0.44557 (15)	1.04935 (7)	0.71677 (11)	0.0296 (2)
C5	0.49353 (17)	0.94719 (9)	0.76029 (13)	0.0207 (2)
C3	0.26124 (16)	0.84858 (8)	0.50943 (12)	0.0178 (2)
C2	0.39451 (16)	0.84873 (8)	0.65765 (12)	0.0176 (2)
C6	0.17301 (17)	0.95080 (10)	0.41030 (13)	0.0220 (2)
O6	0.16203 (15)	0.91197 (8)	0.92116 (12)	0.0334 (3)
O8	0.9298 (2)	0.7500	1.09008 (14)	0.0276 (3)
O7	0.4555 (2)	0.7500	1.09036 (16)	0.0338 (3)
O5	−0.0754 (3)	0.7500	0.72326 (19)	0.0438 (4)
Li2	0.1189 (6)	0.7500	0.9392 (4)	0.0332 (7)
Li1	0.6568 (5)	0.7500	0.9480 (4)	0.0347 (7)
H61	0.071 (3)	0.9536 (18)	0.853 (2)	0.051 (6)*
H62	0.230 (4)	0.962 (2)	0.992 (3)	0.079 (8)*
H81	0.976 (3)	0.8072 (17)	1.148 (2)	0.054 (6)*
H71	0.484 (3)	0.8066 (16)	1.154 (2)	0.044 (5)*
H51	−0.125 (3)	0.8094 (16)	0.661 (2)	0.044 (5)*
H32	0.336 (3)	1.055 (2)	0.588 (2)	0.061 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0231 (6)	0.0119 (5)	0.0173 (5)	0.000	−0.0007 (5)	0.000
N2	0.0242 (7)	0.0148 (6)	0.0177 (6)	0.000	0.0002 (5)	0.000
O4	0.0329 (5)	0.0198 (4)	0.0261 (4)	−0.0035 (3)	−0.0079 (4)	−0.0019 (3)
O2	0.0486 (6)	0.0218 (4)	0.0254 (4)	0.0038 (4)	−0.0124 (4)	0.0033 (3)
O1	0.0485 (6)	0.0135 (4)	0.0257 (4)	0.0029 (4)	−0.0046 (4)	0.0017 (3)
O3	0.0409 (5)	0.0126 (4)	0.0290 (4)	−0.0016 (3)	−0.0047 (4)	−0.0019 (3)
C5	0.0244 (5)	0.0145 (5)	0.0211 (5)	−0.0031 (4)	0.0008 (4)	−0.0018 (4)
C3	0.0220 (5)	0.0130 (5)	0.0166 (4)	0.0011 (4)	0.0011 (4)	0.0014 (4)
C2	0.0212 (5)	0.0130 (4)	0.0168 (4)	−0.0008 (4)	0.0010 (4)	−0.0005 (3)
C6	0.0282 (6)	0.0155 (5)	0.0201 (5)	0.0029 (4)	0.0011 (4)	0.0033 (4)
O6	0.0373 (5)	0.0181 (4)	0.0354 (5)	−0.0004 (4)	−0.0104 (4)	0.0004 (4)
O8	0.0340 (7)	0.0225 (6)	0.0212 (6)	0.000	−0.0037 (5)	0.000
O7	0.0486 (9)	0.0199 (6)	0.0288 (6)	0.000	0.0005 (6)	0.000
O5	0.0585 (10)	0.0214 (7)	0.0379 (8)	0.000	−0.0160 (7)	0.000
Li2	0.0433 (18)	0.0236 (15)	0.0341 (16)	0.000	0.0117 (14)	0.000
Li1	0.0393 (17)	0.0264 (15)	0.0295 (15)	0.000	−0.0099 (13)	0.000

Geometric parameters (Å, º) top

Li1—N1	2.119 (4)	N2—C3ⁱ	1.3324 (12)
Li1—O4	2.1194 (13)	O4—C5	1.2221 (15)
Li1—O8	1.997 (4)	O2—C6	1.2091 (15)
Li1—O7	2.075 (5)	O1—C6	1.2815 (15)
Li1—O4ⁱ	2.1194 (13)	O1—H32	1.19 (2)
Li2—O6	1.9412 (12)	O3—C5	1.2811 (14)
Li2—O7	2.385 (4)	O3—H32	1.21 (2)
Li2—O5	2.052 (4)	C5—C2	1.5279 (15)
Li2—O6ⁱ	1.9412 (12)	C3—C2	1.4081 (15)
Li2—O8ⁱⁱ	2.067 (4)	C3—C6	1.5260 (14)
Li2—Li1ⁱⁱ	3.199 (5)	O6—H61	0.90 (2)
Li1—Li2ⁱⁱⁱ	3.199 (5)	O6—H62	0.91 (3)
O8—Li2ⁱⁱⁱ	2.067 (4)	O8—H81	0.86 (2)
N1—C2ⁱ	1.3277 (12)	O7—H71	0.862 (19)
N1—C2	1.3277 (12)	O5—H51	0.903 (19)
N2—C3	1.3324 (12)

C2ⁱ—N1—C2	122.10 (13)	O6—Li2—O5	90.18 (11)
C2ⁱ—N1—Li1	118.95 (6)	O6ⁱ—Li2—O5	90.18 (11)
C2—N1—Li1	118.95 (6)	O6—Li2—O8ⁱⁱ	100.61 (11)
C3—N2—C3ⁱ	121.05 (13)	O6ⁱ—Li2—O8ⁱⁱ	100.61 (11)
C5—O4—Li1	119.15 (11)	O5—Li2—O8ⁱⁱ	102.98 (18)
C6—O1—H32	116.2 (12)	O6—Li2—O7	84.17 (12)
C5—O3—H32	113.3 (11)	O6ⁱ—Li2—O7	84.17 (12)
O4—C5—O3	123.82 (10)	O5—Li2—O7	148.57 (19)
O4—C5—C2	117.04 (10)	O8ⁱⁱ—Li2—O7	108.45 (15)
O3—C5—C2	119.13 (9)	O6—Li2—Li1ⁱⁱ	100.02 (12)
N2—C3—C2	119.55 (9)	O6ⁱ—Li2—Li1ⁱⁱ	100.02 (12)
N2—C3—C6	112.55 (9)	O5—Li2—Li1ⁱⁱ	65.66 (13)
C2—C3—C6	127.91 (9)	O8ⁱⁱ—Li2—Li1ⁱⁱ	37.32 (10)
N1—C2—C3	118.88 (9)	O7—Li2—Li1ⁱⁱ	145.77 (15)
N1—C2—C5	110.38 (9)	O8—Li1—O7	106.53 (16)
C3—C2—C5	130.71 (9)	O8—Li1—O4ⁱ	102.54 (10)
O2—C6—O1	122.94 (11)	O7—Li1—O4ⁱ	96.41 (12)
O2—C6—C3	118.66 (10)	O8—Li1—O4	102.54 (10)
O1—C6—C3	118.40 (9)	O7—Li1—O4	96.40 (12)
Li2—O6—H61	119.4 (14)	O4ⁱ—Li1—O4	147.18 (17)
Li2—O6—H62	130.5 (17)	O8—Li1—N1	153.3 (2)
H61—O6—H62	106 (2)	O7—Li1—N1	100.14 (17)
Li1—O8—Li2ⁱⁱⁱ	103.81 (16)	O4ⁱ—Li1—N1	74.03 (9)
Li1—O8—H81	122.3 (13)	O4—Li1—N1	74.03 (9)
Li2ⁱⁱⁱ—O8—H81	100.2 (14)	O8—Li1—Li2ⁱⁱⁱ	38.87 (10)
Li1—O7—Li2	111.17 (14)	O7—Li1—Li2ⁱⁱⁱ	145.40 (16)
Li1—O7—H71	107.9 (13)	O4ⁱ—Li1—Li2ⁱⁱⁱ	93.19 (12)
Li2—O7—H71	114.0 (13)	O4—Li1—Li2ⁱⁱⁱ	93.19 (12)
Li2—O5—H51	129.1 (12)	N1—Li1—Li2ⁱⁱⁱ	114.46 (17)
O6—Li2—O6ⁱ	158.1 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O2^iv	0.90 (2)	1.87 (2)	2.7597 (14)	165.4 (19)
O6—H62···O4^v	0.91 (3)	1.91 (3)	2.8129 (14)	173 (2)
O8—H81···O2^vi	0.86 (2)	1.92 (2)	2.7753 (13)	175.9 (19)
O7—H71···O3^v	0.862 (19)	2.037 (19)	2.8950 (12)	173.8 (17)
O5—H51···O1^iv	0.903 (19)	2.010 (19)	2.9110 (13)	175.4 (17)
O1—H32···O3	1.19 (2)	1.21 (2)	2.3894 (15)	173 (2)

Symmetry codes: (iv) −x, −y+2, −z+1; (v) −x+1, −y+2, −z+2; (vi) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula	[Li₂(C₈H₂N₂O₈)(H₂O)₅]
M_r	358.08
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	293
a, b, c (Å)	6.8806 (14), 11.767 (2), 8.8082 (18)
β (°)	103.59 (3)
V (Å³)	693.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.23 × 0.21 × 0.17

Data collection
Diffractometer	Kuma KM-4 four-circle
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.971, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	2291, 2136, 1459
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.127, 1.03
No. of reflections	2136
No. of parameters	148
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.32

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—N1	2.119 (4)	Li2—O6	1.9412 (12)
Li1—O4	2.1194 (13)	Li2—O7	2.385 (4)
Li1—O8	1.997 (4)	Li2—O5	2.052 (4)
Li1—O7	2.075 (5)	Li2—O6ⁱ	1.9412 (12)
Li1—O4ⁱ	2.1194 (13)	Li2—O8ⁱⁱ	2.067 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O2ⁱⁱⁱ	0.90 (2)	1.87 (2)	2.7597 (14)	165.4 (19)
O6—H62···O4^iv	0.91 (3)	1.91 (3)	2.8129 (14)	173 (2)
O8—H81···O2^v	0.86 (2)	1.92 (2)	2.7753 (13)	175.9 (19)
O7—H71···O3^iv	0.862 (19)	2.037 (19)	2.8950 (12)	173.8 (17)
O5—H51···O1ⁱⁱⁱ	0.903 (19)	2.010 (19)	2.9110 (13)	175.4 (17)
O1—H32···O3	1.19 (2)	1.21 (2)	2.3894 (15)	173 (2)

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

References

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