Poly[diaqua(μ2-oxalato-κ4O1,O2:O1′,O2′)(μ2-pyrazine-2-carboxyl­ato-κ3N1,O:O′)cerium(III)]

Wang, Y.; Wang, C.

doi:10.1107/S1600536808029164

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages m1282-m1283

doi:10.1107/S1600536808029164

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Poly[diaqua(μ₂-oxalato-κ⁴O¹,O²:O^1′,O^2′)(μ₂-pyrazine-2-carboxylato-κ³N¹,O:O′)cerium(III)]

Yuanlan Wang ^a and Chongchen Wang ^b ^*

^aResearch Institute of Applied Chemistry, Central South University of Forestry and Technology, 412006 Zhuzhou, Hunan, People's Republic of China, and ^bSchool of Environmental and Energy Engineering, Beijing University of Civil Engineering and Architecture, 100044 Beijing, People's Republic of China
^*Correspondence e-mail: chongchenwang@126.com

(Received 20 August 2008; accepted 11 September 2008; online 20 September 2008)

In the hydrothermally synthesized title compound, [Ce(C₅H₃N₂O₂)(C₂O₄)(H₂O)₂]_n, the Ce^III ion is coordinated by four O atoms from two different oxalate ligands, three O atoms from two symmetry-related pyrazine-2-carboxylate ligands, two O atoms from two water melecules and one N atom from a pyrazine-2-carboxylate ligand in a distorted bicapped square-antiprismatic coordination geometry. The oxalate and pyrazine-2-carboxylate ligands bridge the Ce^III ions, forming a two-dimensional structure. In addition, intermolecular O—H⋯O and O—H⋯N hydrogen bonds connect the two-dimensional structure into a three-dimensional network.

Related literature

For background information, see: Eliseeva et al. (2004 ); Wang et al. (2007 ); Zou et al. (1999 ); Zheng et al. (2002 ).

Experimental

Crystal data

[Ce(C₅H₃N₂O₂)(C₂O₄)(H₂O)₂]
M_r = 387.27
Triclinic, $[P \overline 1]$
a = 8.0298 (7) Å
b = 8.7161 (9) Å
c = 8.8201 (9) Å
α = 115.514 (2)°
β = 101.747 (1)°
γ = 95.999 (1)°
V = 532.38 (9) Å³
Z = 2
Mo Kα radiation
μ = 4.31 mm⁻¹
T = 298 (2) K
0.24 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.424, T_max = 0.672
2790 measured reflections
1858 independent reflections
1760 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.049
S = 1.09
1858 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Table 1
Selected bond lengths (Å)

Ce1—O8	2.506 (2)
Ce1—O4ⁱ	2.521 (2)
Ce1—O5	2.530 (2)
Ce1—O3	2.538 (2)
Ce1—O6ⁱⁱ	2.540 (2)
Ce1—O1	2.578 (2)
Ce1—O7	2.595 (3)
Ce1—O1ⁱⁱⁱ	2.614 (2)
Ce1—N1	2.815 (3)
Ce1—O2ⁱⁱⁱ	2.897 (3)
Symmetry codes: (i) -x+1, -y+2, -z+3; (ii) -x, -y+1, -z+2; (iii) -x+1, -y+1, -z+3.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O5^iv	0.85	2.10	2.836 (4)	145
O7—H7B⋯O2^v	0.85	1.94	2.738 (4)	156
O8—H8A⋯N2^vi	0.85	1.96	2.799 (4)	169
O8—H8B⋯O3ⁱⁱⁱ	0.85	2.05	2.873 (3)	163
Symmetry codes: (iii) -x+1, -y+1, -z+3; (iv) -x+1, -y+1, -z+2; (v) x, y, z-1; (vi) x, y-1, z-1.

Data collection: SMART (Bruker, 1996 ); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536808029164/lh2687sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029164/lh2687Isup2.hkl

checkCIF report

Comment top

Rare metal coordination polymers of one-, two- and three-dimensional extended frameworks are an attractive research area because of the diverse structures available (Zheng, 2002; Eliseeva et al., 2004). Pyrazine-2,3-dicaboxylic acid is a good ligand with a versatitle coordination mode, which is widely used in self-assembled polymeric coordination synthesis (Zou et al., 1999; Wang et al., 2007). The title compound, [Ce(C₅H₃N₂O₂)(C₂O₄)(H₂O)₂]_n, was obtained unintentionally as the harvested product of the hydrothermal reaction of pyrazine-2,3-dicaboxylic acid and Ce₂(C₂O₄)₃.10H₂O. We report here the crystal structure of the title compound, a 2-D polymeric structure consisting of pyrazine-2-dicaboxylate and oxalate ligands.

The coordination environment of the Ce^III ion can be described as a distorted bicapped square-antiprism, in which the Ce^III ion is ten-coordinated by four oxygen atoms from two different oxalate ligands, three oxygen atoms from two different pyrazine -2-carboxylic acid ligands, two oxygen atoms from two water molecules, and one nitrogen atom from a pyrazine-2-carboxylate ligand, as shown in the Fig. 1. The oxalate ligands and pyrazine-2-carboxylate ligands bridge Ce^III ions to form a two-dimensional structure. The Ce—O bond lengths range from 2.506 (2) to 2.897 (3) Å. In the crystal structure, intermolecular O—H···O and O—H···N hydrogen bonds connect the two-dimensional structure into a three dimensional network.

Related literature top

For background information, see: Eliseeva et al. (2004); Wang et al. (2007); Zou et al. (1999); Zheng et al. (2002).

Experimental top

Colorless block-shaped crystals of the title compound were obtained by a hydrothermal reaction of Ce₂(C₂O₄)₃.10H₂O (0.10 mmol, 0.0710 g), pyrazine-2,3-dicarboxylic acid (0.10 mmol, 0.0168 g) and deionized water (15 ml) in a 23 ml teflon-lined reaction vesset at 423 K for 120 h followed by slow cooling to room temperature (yield 77% based on initial input of pyrazine-2,3-dicarboxylic acid).

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996; 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. The asymmetric unit of the title compound with symmetry related atoms included to show the coordination environment of Ce1. Displacement ellipsoids are drawn at the 40% probability level [Symmetry codes: (A) -x + 1, -y + 2, -z + 3, (B) -x+1, -y+2, -z+3, (C) -x, -y+1, -z+2].
	Fig. 2. Part of the crystal structure showing hydrogen bonds as dashed lines.

Poly[diaqua(µ₂-oxalato- κ⁴O¹,O²:O^1',O^2')(µ₂-pyrazine- 2-carboxylato-κ³N¹,O:O')cerium(III)] top

Crystal data top

[Ce(C₅H₃N₂O₂)(C₂O₄)(H₂O)₂]	Z = 2
M_r = 387.27	F(000) = 370
Triclinic, P1	D_x = 2.416 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0298 (7) Å	Cell parameters from 2791 reflections
b = 8.7161 (9) Å	θ = 2.7–28.5°
c = 8.8201 (9) Å	µ = 4.31 mm⁻¹
α = 115.514 (2)°	T = 298 K
β = 101.747 (1)°	Block, colourless
γ = 95.999 (1)°	0.24 × 0.15 × 0.10 mm
V = 532.38 (9) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	1858 independent reflections
Radiation source: fine-focus sealed tube	1760 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→9
T_min = 0.424, T_max = 0.672	k = −10→10
2790 measured reflections	l = −10→8

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0274P)² + 0.3347P] where P = (F_o² + 2F_c²)/3
1858 reflections	(Δ/σ)_max = 0.002
163 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.95 e Å⁻³

Crystal data top

[Ce(C₅H₃N₂O₂)(C₂O₄)(H₂O)₂]	γ = 95.999 (1)°
M_r = 387.27	V = 532.38 (9) Å³
Triclinic, P1	Z = 2
a = 8.0298 (7) Å	Mo Kα radiation
b = 8.7161 (9) Å	µ = 4.31 mm⁻¹
c = 8.8201 (9) Å	T = 298 K
α = 115.514 (2)°	0.24 × 0.15 × 0.10 mm
β = 101.747 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1858 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1760 reflections with I > 2σ(I)
T_min = 0.424, T_max = 0.672	R_int = 0.013
2790 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.049	H-atom parameters constrained
S = 1.09	Δρ_max = 0.68 e Å⁻³
1858 reflections	Δρ_min = −0.95 e Å⁻³
163 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
Ce1	0.33921 (2)	0.58558 (2)	1.32325 (2)	0.01398 (8)
N1	0.1921 (4)	0.7628 (4)	1.5966 (4)	0.0211 (6)
N2	0.1556 (4)	1.0173 (4)	1.9097 (4)	0.0265 (7)
O1	0.3927 (3)	0.5389 (3)	1.5971 (3)	0.0193 (5)
O2	0.4946 (3)	0.6763 (4)	1.8853 (3)	0.0287 (6)
O3	0.5575 (3)	0.8498 (3)	1.5730 (3)	0.0214 (5)
O4	0.6890 (3)	1.1263 (3)	1.6700 (3)	0.0224 (5)
O5	0.2132 (3)	0.4771 (4)	0.9986 (3)	0.0257 (6)
O6	−0.0157 (3)	0.4293 (4)	0.7792 (3)	0.0257 (6)
O7	0.5757 (3)	0.6984 (3)	1.2121 (3)	0.0251 (6)
H7A	0.6535	0.6401	1.1878	0.030*
H7B	0.5255	0.7040	1.1205	0.030*
O8	0.2021 (3)	0.2812 (3)	1.2493 (3)	0.0228 (5)
H8A	0.1736	0.2001	1.1447	0.027*
H8B	0.2566	0.2414	1.3126	0.027*
C1	0.3960 (4)	0.6567 (4)	1.7474 (5)	0.0186 (7)
C2	0.2763 (4)	0.7791 (4)	1.7518 (5)	0.0194 (7)
C3	0.2585 (5)	0.9048 (5)	1.9071 (5)	0.0258 (8)
H3	0.3192	0.9114	2.0122	0.031*
C4	0.0669 (5)	0.9965 (5)	1.7544 (5)	0.0273 (8)
H4	−0.0092	1.0689	1.7502	0.033*
C5	0.0845 (5)	0.8704 (5)	1.5992 (5)	0.0264 (8)
H5	0.0197	0.8603	1.4939	0.032*
C6	0.5713 (4)	0.9932 (4)	1.5705 (4)	0.0159 (7)
C7	0.0567 (4)	0.4734 (4)	0.9350 (4)	0.0187 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ce1	0.01536 (12)	0.01406 (12)	0.01362 (12)	0.00340 (8)	0.00329 (8)	0.00769 (9)
N1	0.0232 (16)	0.0251 (16)	0.0198 (16)	0.0104 (13)	0.0082 (12)	0.0127 (13)
N2	0.0270 (17)	0.0240 (16)	0.0273 (18)	0.0080 (13)	0.0117 (14)	0.0084 (14)
O1	0.0259 (13)	0.0191 (12)	0.0190 (13)	0.0111 (10)	0.0106 (10)	0.0108 (10)
O2	0.0305 (15)	0.0407 (16)	0.0213 (14)	0.0144 (12)	0.0069 (11)	0.0185 (12)
O3	0.0258 (13)	0.0179 (12)	0.0206 (13)	0.0034 (10)	0.0015 (10)	0.0115 (10)
O4	0.0215 (13)	0.0180 (12)	0.0264 (14)	0.0034 (10)	0.0006 (11)	0.0120 (11)
O5	0.0162 (13)	0.0410 (16)	0.0198 (13)	0.0090 (11)	0.0044 (10)	0.0138 (12)
O6	0.0200 (13)	0.0389 (15)	0.0165 (13)	0.0077 (11)	0.0033 (10)	0.0118 (12)
O7	0.0266 (14)	0.0329 (15)	0.0230 (14)	0.0106 (11)	0.0128 (11)	0.0157 (12)
O8	0.0283 (14)	0.0169 (12)	0.0202 (13)	0.0021 (10)	0.0042 (11)	0.0077 (11)
C1	0.0210 (18)	0.0223 (18)	0.0204 (19)	0.0057 (14)	0.0096 (14)	0.0151 (15)
C2	0.0201 (18)	0.0201 (17)	0.0225 (18)	0.0069 (14)	0.0087 (14)	0.0120 (15)
C3	0.026 (2)	0.028 (2)	0.0213 (19)	0.0070 (16)	0.0066 (15)	0.0098 (16)
C4	0.030 (2)	0.027 (2)	0.032 (2)	0.0126 (16)	0.0133 (17)	0.0166 (17)
C5	0.030 (2)	0.032 (2)	0.026 (2)	0.0148 (17)	0.0102 (16)	0.0180 (17)
C6	0.0176 (17)	0.0146 (17)	0.0178 (17)	0.0049 (13)	0.0068 (14)	0.0085 (14)
C7	0.0201 (18)	0.0203 (18)	0.0183 (18)	0.0038 (14)	0.0060 (15)	0.0109 (15)

Geometric parameters (Å, º) top

Ce1—O8	2.506 (2)	O3—C6	1.254 (4)
Ce1—O4ⁱ	2.521 (2)	O4—C6	1.251 (4)
Ce1—O5	2.530 (2)	O4—Ce1ⁱ	2.521 (2)
Ce1—O3	2.538 (2)	O5—C7	1.259 (4)
Ce1—O6ⁱⁱ	2.540 (2)	O6—C7	1.244 (4)
Ce1—O1	2.578 (2)	O6—Ce1ⁱⁱ	2.540 (2)
Ce1—O7	2.595 (3)	O7—H7A	0.8500
Ce1—O1ⁱⁱⁱ	2.614 (2)	O7—H7B	0.8500
Ce1—N1	2.815 (3)	O8—H8A	0.8500
Ce1—O2ⁱⁱⁱ	2.897 (3)	O8—H8B	0.8500
N1—C5	1.337 (5)	C1—C2	1.502 (5)
N1—C2	1.337 (5)	C2—C3	1.384 (5)
N2—C4	1.333 (5)	C3—H3	0.9300
N2—C3	1.343 (5)	C4—C5	1.385 (5)
O1—C1	1.273 (4)	C4—H4	0.9300
O1—Ce1ⁱⁱⁱ	2.614 (2)	C5—H5	0.9300
O2—C1	1.240 (4)	C6—C6ⁱ	1.564 (6)
O2—Ce1ⁱⁱⁱ	2.897 (3)	C7—C7ⁱⁱ	1.554 (7)

O8—Ce1—O4ⁱ	149.92 (8)	O7—Ce1—O2ⁱⁱⁱ	64.80 (8)
O8—Ce1—O5	82.87 (9)	O1ⁱⁱⁱ—Ce1—O2ⁱⁱⁱ	46.97 (7)
O4ⁱ—Ce1—O5	81.64 (8)	N1—Ce1—O2ⁱⁱⁱ	157.52 (8)
O8—Ce1—O3	139.44 (8)	C5—N1—C2	116.2 (3)
O4ⁱ—Ce1—O3	64.55 (7)	C5—N1—Ce1	126.2 (2)
O5—Ce1—O3	136.12 (8)	C2—N1—Ce1	114.7 (2)
O8—Ce1—O6ⁱⁱ	76.91 (9)	C4—N2—C3	116.2 (3)
O4ⁱ—Ce1—O6ⁱⁱ	73.14 (8)	C1—O1—Ce1	122.9 (2)
O5—Ce1—O6ⁱⁱ	63.80 (8)	C1—O1—Ce1ⁱⁱⁱ	100.9 (2)
O3—Ce1—O6ⁱⁱ	124.88 (8)	Ce1—O1—Ce1ⁱⁱⁱ	119.65 (9)
O8—Ce1—O1	68.68 (8)	C1—O2—Ce1ⁱⁱⁱ	88.3 (2)
O4ⁱ—Ce1—O1	123.57 (8)	C6—O3—Ce1	119.4 (2)
O5—Ce1—O1	151.55 (9)	C6—O4—Ce1ⁱ	120.1 (2)
O3—Ce1—O1	71.80 (8)	C7—O5—Ce1	121.5 (2)
O6ⁱⁱ—Ce1—O1	107.92 (8)	C7—O6—Ce1ⁱⁱ	121.0 (2)
O8—Ce1—O7	130.61 (8)	Ce1—O7—H7A	117.4
O4ⁱ—Ce1—O7	67.79 (8)	Ce1—O7—H7B	108.6
O5—Ce1—O7	72.58 (8)	H7A—O7—H7B	107.4
O3—Ce1—O7	69.25 (8)	Ce1—O8—H8A	120.9
O6ⁱⁱ—Ce1—O7	124.39 (8)	Ce1—O8—H8B	114.4
O1—Ce1—O7	126.31 (8)	H8A—O8—H8B	106.6
O8—Ce1—O1ⁱⁱⁱ	77.10 (8)	O2—C1—O1	123.3 (3)
O4ⁱ—Ce1—O1ⁱⁱⁱ	132.90 (8)	O2—C1—C2	120.1 (3)
O5—Ce1—O1ⁱⁱⁱ	114.25 (8)	O1—C1—C2	116.6 (3)
O3—Ce1—O1ⁱⁱⁱ	75.86 (7)	N1—C2—C3	122.0 (3)
O6ⁱⁱ—Ce1—O1ⁱⁱⁱ	153.96 (9)	N1—C2—C1	115.8 (3)
O1—Ce1—O1ⁱⁱⁱ	60.35 (9)	C3—C2—C1	122.2 (3)
O7—Ce1—O1ⁱⁱⁱ	75.23 (8)	N2—C3—C2	121.6 (4)
O8—Ce1—N1	97.71 (9)	N2—C3—H3	119.2
O4ⁱ—Ce1—N1	72.66 (9)	C2—C3—H3	119.2
O5—Ce1—N1	128.42 (8)	N2—C4—C5	122.1 (3)
O3—Ce1—N1	68.56 (9)	N2—C4—H4	119.0
O6ⁱⁱ—Ce1—N1	66.20 (8)	C5—C4—H4	119.0
O1—Ce1—N1	58.85 (8)	N1—C5—C4	121.8 (3)
O7—Ce1—N1	131.17 (9)	N1—C5—H5	119.1
O1ⁱⁱⁱ—Ce1—N1	116.07 (8)	C4—C5—H5	119.1
O8—Ce1—O2ⁱⁱⁱ	66.33 (8)	O4—C6—O3	126.0 (3)
O4ⁱ—Ce1—O2ⁱⁱⁱ	129.05 (8)	O4—C6—C6ⁱ	117.0 (3)
O5—Ce1—O2ⁱⁱⁱ	67.54 (8)	O3—C6—C6ⁱ	117.0 (4)
O3—Ce1—O2ⁱⁱⁱ	112.59 (8)	O6—C7—O5	126.5 (3)
O6ⁱⁱ—Ce1—O2ⁱⁱⁱ	121.33 (8)	O6—C7—C7ⁱⁱ	117.4 (4)
O1—Ce1—O2ⁱⁱⁱ	99.44 (7)	O5—C7—C7ⁱⁱ	116.1 (4)

O8—Ce1—N1—C5	−117.5 (3)	O1ⁱⁱⁱ—Ce1—O3—C6	142.2 (3)
O4ⁱ—Ce1—N1—C5	33.2 (3)	N1—Ce1—O3—C6	−91.9 (2)
O5—Ce1—N1—C5	−30.5 (4)	O2ⁱⁱⁱ—Ce1—O3—C6	112.3 (2)
O3—Ce1—N1—C5	102.1 (3)	O8—Ce1—O5—C7	82.8 (3)
O6ⁱⁱ—Ce1—N1—C5	−45.6 (3)	O4ⁱ—Ce1—O5—C7	−71.3 (3)
O1—Ce1—N1—C5	−176.8 (3)	O3—Ce1—O5—C7	−110.1 (3)
O7—Ce1—N1—C5	70.2 (3)	O6ⁱⁱ—Ce1—O5—C7	3.9 (3)
O1ⁱⁱⁱ—Ce1—N1—C5	163.1 (3)	O1—Ce1—O5—C7	83.1 (3)
O2ⁱⁱⁱ—Ce1—N1—C5	−160.4 (3)	O7—Ce1—O5—C7	−140.6 (3)
O8—Ce1—N1—C2	82.8 (3)	O1ⁱⁱⁱ—Ce1—O5—C7	155.2 (3)
O4ⁱ—Ce1—N1—C2	−126.4 (3)	N1—Ce1—O5—C7	−11.4 (3)
O5—Ce1—N1—C2	169.8 (2)	O2ⁱⁱⁱ—Ce1—O5—C7	150.1 (3)
O3—Ce1—N1—C2	−57.6 (2)	Ce1ⁱⁱⁱ—O2—C1—O1	6.9 (3)
O6ⁱⁱ—Ce1—N1—C2	154.8 (3)	Ce1ⁱⁱⁱ—O2—C1—C2	−171.1 (3)
O1—Ce1—N1—C2	23.5 (2)	Ce1—O1—C1—O2	−144.3 (3)
O7—Ce1—N1—C2	−89.5 (3)	Ce1ⁱⁱⁱ—O1—C1—O2	−7.8 (4)
O1ⁱⁱⁱ—Ce1—N1—C2	3.4 (3)	Ce1—O1—C1—C2	33.8 (4)
O2ⁱⁱⁱ—Ce1—N1—C2	39.9 (4)	Ce1ⁱⁱⁱ—O1—C1—C2	170.3 (3)
O8—Ce1—O1—C1	−144.1 (3)	C5—N1—C2—C3	−2.5 (5)
O4ⁱ—Ce1—O1—C1	4.7 (3)	Ce1—N1—C2—C3	159.3 (3)
O5—Ce1—O1—C1	−144.4 (2)	C5—N1—C2—C1	179.6 (3)
O3—Ce1—O1—C1	45.2 (2)	Ce1—N1—C2—C1	−18.6 (4)
O6ⁱⁱ—Ce1—O1—C1	−76.6 (3)	O2—C1—C2—N1	171.3 (3)
O7—Ce1—O1—C1	90.4 (3)	O1—C1—C2—N1	−6.8 (5)
O1ⁱⁱⁱ—Ce1—O1—C1	129.0 (3)	O2—C1—C2—C3	−6.6 (5)
N1—Ce1—O1—C1	−30.3 (2)	O1—C1—C2—C3	175.3 (3)
O2ⁱⁱⁱ—Ce1—O1—C1	156.0 (3)	C4—N2—C3—C2	2.5 (6)
O8—Ce1—O1—Ce1ⁱⁱⁱ	86.94 (11)	N1—C2—C3—N2	−0.1 (6)
O4ⁱ—Ce1—O1—Ce1ⁱⁱⁱ	−124.21 (10)	C1—C2—C3—N2	177.7 (3)
O5—Ce1—O1—Ce1ⁱⁱⁱ	86.64 (18)	C3—N2—C4—C5	−2.4 (6)
O3—Ce1—O1—Ce1ⁱⁱⁱ	−83.76 (11)	C2—N1—C5—C4	2.6 (6)
O6ⁱⁱ—Ce1—O1—Ce1ⁱⁱⁱ	154.49 (10)	Ce1—N1—C5—C4	−156.8 (3)
O7—Ce1—O1—Ce1ⁱⁱⁱ	−38.53 (14)	N2—C4—C5—N1	−0.2 (6)
O1ⁱⁱⁱ—Ce1—O1—Ce1ⁱⁱⁱ	0.0	Ce1ⁱ—O4—C6—O3	−168.9 (3)
N1—Ce1—O1—Ce1ⁱⁱⁱ	−159.23 (14)	Ce1ⁱ—O4—C6—C6ⁱ	11.3 (5)
O2ⁱⁱⁱ—Ce1—O1—Ce1ⁱⁱⁱ	27.05 (11)	Ce1—O3—C6—O4	−169.0 (3)
O8—Ce1—O3—C6	−168.2 (2)	Ce1—O3—C6—C6ⁱ	10.8 (5)
O4ⁱ—Ce1—O3—C6	−11.6 (2)	Ce1ⁱⁱ—O6—C7—O5	176.2 (3)
O5—Ce1—O3—C6	31.8 (3)	Ce1ⁱⁱ—O6—C7—C7ⁱⁱ	−2.7 (5)
O6ⁱⁱ—Ce1—O3—C6	−55.2 (3)	Ce1—O5—C7—O6	176.9 (3)
O1—Ce1—O3—C6	−154.8 (3)	Ce1—O5—C7—C7ⁱⁱ	−4.2 (5)
O7—Ce1—O3—C6	62.9 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O5^iv	0.85	2.10	2.836 (4)	145
O7—H7B···O2^v	0.85	1.94	2.738 (4)	156
O8—H8A···N2^vi	0.85	1.96	2.799 (4)	169
O8—H8B···O3ⁱⁱⁱ	0.85	2.05	2.873 (3)	163

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

Experimental details

Crystal data
Chemical formula	[Ce(C₅H₃N₂O₂)(C₂O₄)(H₂O)₂]
M_r	387.27
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.0298 (7), 8.7161 (9), 8.8201 (9)
α, β, γ (°)	115.514 (2), 101.747 (1), 95.999 (1)
V (Å³)	532.38 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.31
Crystal size (mm)	0.24 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.424, 0.672
No. of measured, independent and observed [I > 2σ(I)] reflections	2790, 1858, 1760
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.049, 1.09
No. of reflections	1858
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.95

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), SAINT (Bruker, 1996, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ce1—O8	2.506 (2)	Ce1—O1	2.578 (2)
Ce1—O4ⁱ	2.521 (2)	Ce1—O7	2.595 (3)
Ce1—O5	2.530 (2)	Ce1—O1ⁱⁱⁱ	2.614 (2)
Ce1—O3	2.538 (2)	Ce1—N1	2.815 (3)
Ce1—O6ⁱⁱ	2.540 (2)	Ce1—O2ⁱⁱⁱ	2.897 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O5^iv	0.85	2.10	2.836 (4)	145.3
O7—H7B···O2^v	0.85	1.94	2.738 (4)	155.7
O8—H8A···N2^vi	0.85	1.96	2.799 (4)	169.1
O8—H8B···O3ⁱⁱⁱ	0.85	2.05	2.873 (3)	162.8

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

Acknowledgements

The authors gratefully acknowledge the financial support of the Research Fund of Beijing University of Civil Engineering and Architecture (grant No. 100700502) and the Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of Beijing Municipality (grant No. BJE10016200611).

References

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