Poly[[hexa­aqua­(μ2-oxalato-κ4O1,O2:O1′,O2′)bis(μ3-pyridine-2,4-dicarboxyl­ato-κ4N,O1:O1′:O4)dicerium(III)] monohydrate]

Shen, F.M.; Lush, S.F.

doi:10.1107/S1600536811051956

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages m21-m22

doi:10.1107/S1600536811051956

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Poly[[hexaaqua(μ₂-oxalato-κ⁴O¹,O²:O^1′,O^2′)bis(μ₃-pyridine-2,4-dicarboxylato-κ⁴N,O¹:O^1′:O⁴)dicerium(III)] monohydrate]

Fwu Ming Shen ^a and Shie Fu Lush ^b ^*

^aDepartment of Biotechnology, Yuanpei University, HsinChu 30015, Taiwan, and ^bDepartment of General Education Center, Yuanpei University, HsinChu 30015, Taiwan
^*Correspondence e-mail: lush@mail.ypu.edu.tw

(Received 28 November 2011; accepted 1 December 2011; online 7 December 2011)

In the polymeric title compound, {[Ce₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O}_n, the Ce³⁺ cation is nine-coordinated in a distorted CeNO₈ tricapped trigonal–prismatic geometry, formed by three pyridine-2,4-dicarboxylate anions, one oxalate anion and three water molecules. The mid-point of the oxalate anion is located on an inversion center. The oxalate and pyridine-2,4-dicarboxylate anions bridge the Ce³⁺ cations, forming a two-dimensional polymeric complex parallel to (010). Intermolecular classical O—H⋯O hydrogen bonding and weak C—H⋯O hydrogen bonding are present in the crystal structure and π–π stacking [centroid–centroid distance = 3.558 (2) Å] is observed between parallel pyridine rings of adjacent molecules. The uncoordinated water molecule shows an occupancy of 0.5.

Related literature

For the isotypic La³⁺ complex, see: Shen & Lush (2011 ). For related pyridine-2,4-dicarboxylate complexes, see: Aghabozorg et al. (2011 ); Li et al. (2007 ); Wang et al. (2009 ).

Experimental

Crystal data

[Ce₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O
M_r = 824.58
Triclinic, $[P \overline 1]$
a = 6.4160 (5) Å
b = 6.6486 (6) Å
c = 13.9920 (12) Å
α = 89.917 (1)°
β = 85.588 (1)°
γ = 73.676 (1)°
V = 570.98 (8) Å³
Z = 1
Mo Kα radiation
μ = 4.04 mm⁻¹
T = 294 K
0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.639, T_max = 0.937
6072 measured reflections
2664 independent reflections
2416 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.081
S = 1.10
2664 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 2.75 e Å⁻³
Δρ_min = −2.70 e Å⁻³

Table 1
Selected bond lengths (Å)

Ce—N1	2.684 (3)
Ce—O1ⁱ	2.409 (4)
Ce—O3ⁱⁱ	2.505 (3)
Ce—O4	2.511 (3)
Ce—O5	2.508 (3)
Ce—O6ⁱⁱⁱ	2.515 (3)
Ce—O7	2.568 (5)
Ce—O8	2.515 (4)
Ce—O9	2.582 (5)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O4ⁱⁱ	0.86	2.03	2.879 (6)	171
O7—H7B⋯O10^iv	0.83	1.84	2.569 (10)	146
O8—H8A⋯O6^v	0.92	2.00	2.910 (5)	170
O8—H8B⋯O2^vi	0.86	1.84	2.655 (6)	159
O9—H9A⋯O6^v	0.99	2.01	2.987 (6)	169
O9—H9B⋯O10	0.84	1.93	2.440 (10)	118
O10—H10A⋯O5ⁱⁱ	0.84	2.12	2.844 (9)	143
O10—H10A⋯O8ⁱⁱ	0.84	2.39	2.913 (10)	121
O10—H10B⋯O9^vii	0.94	1.63	2.501 (11)	153
C5—H5A⋯O3ⁱⁱ	0.93	2.46	3.131 (5)	129
Symmetry codes: (ii) x-1, y, z; (iv) x, y+1, z; (v) -x+1, -y, -z+2; (vi) -x+2, -y, -z+1; (vii) -x, -y, -z+2.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051956/xu5400sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051956/xu5400Isup2.hkl

checkCIF report

Comment top

The pyridine-2,4-dicarboxylic acid (pdcH2) has important coordination functions to metals by either carboxylate bridges between metal centers, to form dimeric complexes or tridentate (O, N, O') chelation to metal ions. Some pydc complexes have been reported (Li et al., 2007; Wang et al., 2009; Aghabozorg et al., 2011).

The title complex is isomorphous with the La³⁺ complex (Shen & Lush, 2011). The Ce^III is nine-coordinated in a distorted tricapped trigonal prismatic geometry formed by N and O atoms from a pydc ligand, two O atoms from two pydc ligands, two O atoms from one oxalate ligand and three O atoms from coordinated water molecules (shown as Fig. 1, Table 1). The mid-point of the oxalate anion is located on an inversion center. The oxalate and pyridinedicarboxylate anions bridge the Ce³⁺ cations to form the polymeric complex (Fig. 2).

The crystal structure contains O—H···O and weak C—H···O hydrogen bonds. The π-π stacking between two pyridine rings of (pydc) anion fragments with centroids distance of 3.558 (2) Å (1 - x, 1 - y, 1 - z) are observed. The uncoordinated water molecule shows half-occupation.

Related literature top

For the isotypic La³⁺ complex, see: Shen & Lush (2011). For related pyridine-2,4-dicarboxylate complexes, see: Aghabozorg et al. (2011); Li et al. (2007); Wang et al. (2009).

Experimental top

Ce(NO₃)₃.6H2O (0.1086 g, 0.25 mmole), pydridine-2,4-dicarboxylic acid (0.0418 g, 0.25 mmol) and 4,4'-dipyridine (0.0464 g, 0.25 mmol) were mixed in 10 ml of deionized water. After stirring for 30 min, the mixture was placed in a 23 ml Teflon-lined reactor which was heated under autogenous pressure to 418 K for 48 h and then allowed to cool to room temperature. The colorless transparent single crystals were obtained in 35.6% yield (based on Ce).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. All H atoms have been omitted for clarity. [Symmetry code: (i) x - 1, y, z; (ii) -x + 1, -y + 1, -z + 1; (iii) -x + 1, -y + 1, -z + 2.]
	Fig. 2. The crystal packing of (I) viewed along the c axis. Hydrogen bonds are shown as dashed lines.

Poly[[hexaaqua(µ₂-oxalato- κ⁴O¹,O²:O^1',O^2')bis(µ₃-pyridine- 2,4-dicarboxylato- κ⁴N,O¹:O^1':O⁴)dicerium(III)] monohydrate] top

Crystal data top

[Ce₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O	Z = 1
M_r = 824.58	F(000) = 398
Triclinic, P1	D_x = 2.398 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4160 (5) Å	Cell parameters from 4490 reflections
b = 6.6486 (6) Å	θ = 2.5–25.0°
c = 13.9920 (12) Å	µ = 4.04 mm⁻¹
α = 89.917 (1)°	T = 294 K
β = 85.588 (1)°	Columnar, colorless
γ = 73.676 (1)°	0.30 × 0.10 × 0.10 mm
V = 570.98 (8) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2664 independent reflections
Radiation source: fine-focus sealed tube	2416 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 9 pixels mm^-1	θ_max = 27.8°, θ_min = 1.5°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −8→8
T_min = 0.639, T_max = 0.937	l = −18→18
6072 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0523P)² + 0.4154P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.019
2664 reflections	Δρ_max = 2.75 e Å⁻³
177 parameters	Δρ_min = −2.70 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (15)

Crystal data top

[Ce₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O	γ = 73.676 (1)°
M_r = 824.58	V = 570.98 (8) Å³
Triclinic, P1	Z = 1
a = 6.4160 (5) Å	Mo Kα radiation
b = 6.6486 (6) Å	µ = 4.04 mm⁻¹
c = 13.9920 (12) Å	T = 294 K
α = 89.917 (1)°	0.30 × 0.10 × 0.10 mm
β = 85.588 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2664 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2416 reflections with I > 2σ(I)
T_min = 0.639, T_max = 0.937	R_int = 0.030
6072 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.10	Δρ_max = 2.75 e Å⁻³
2664 reflections	Δρ_min = −2.70 e Å⁻³
177 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	Occ. (<1)
Ce	0.36484 (3)	0.33000 (3)	0.80343 (1)	0.0198 (1)
O1	0.7620 (6)	0.3463 (6)	0.2798 (2)	0.0356 (11)
O2	1.0901 (6)	0.2177 (7)	0.3373 (3)	0.0438 (13)
O3	1.0817 (5)	0.2746 (6)	0.7009 (2)	0.0350 (10)
O4	0.7595 (5)	0.3214 (7)	0.7822 (2)	0.0380 (13)
O5	0.5054 (7)	0.2476 (5)	0.9655 (2)	0.0408 (13)
O6	0.5773 (6)	0.3678 (5)	1.1047 (2)	0.0360 (10)
O7	0.0036 (8)	0.5134 (8)	0.8992 (4)	0.0729 (14)
O8	0.5654 (6)	−0.0533 (6)	0.7844 (3)	0.0419 (11)
O9	0.1789 (8)	0.0870 (8)	0.8994 (4)	0.0729 (14)
N1	0.5723 (5)	0.2600 (6)	0.6274 (2)	0.0208 (9)
C1	0.7770 (7)	0.2748 (6)	0.6150 (3)	0.0218 (11)
C2	0.5683 (7)	0.2406 (7)	0.4556 (3)	0.0248 (11)
C3	0.7772 (7)	0.2622 (7)	0.4439 (3)	0.0227 (11)
C4	0.8836 (7)	0.2747 (7)	0.5250 (3)	0.0251 (11)
C5	0.4745 (7)	0.2392 (7)	0.5484 (3)	0.0256 (12)
C6	0.8875 (8)	0.2745 (7)	0.3451 (3)	0.0275 (12)
C7	0.8828 (7)	0.2921 (7)	0.7052 (3)	0.0246 (11)
C8	0.5247 (7)	0.3884 (6)	1.0201 (3)	0.0237 (11)
O10	−0.1094 (13)	−0.0862 (13)	0.9223 (7)	0.050 (3)	0.500
H2A	0.49300	0.22740	0.40290	0.039 (15)*
H4A	1.02630	0.28290	0.51910	0.0300*
H5A	0.33490	0.22280	0.55600	0.0300*
H7A	−0.07800	0.47060	0.86320	0.0800*
H7B	−0.02500	0.63680	0.88280	0.0800*
H8A	0.53670	−0.16200	0.81820	0.0800*
H8B	0.65420	−0.09500	0.73490	0.0800*
H9A	0.24360	−0.06740	0.89420	0.0800*
H9B	0.06500	0.09050	0.87300	0.0800*
H10A	−0.21970	0.00790	0.90760	0.0800*	0.500
H10B	−0.12520	−0.12960	0.98560	0.0800*	0.500

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ce	0.0191 (2)	0.0294 (2)	0.0134 (1)	−0.0113 (1)	−0.0006 (1)	0.0005 (1)
O1	0.0380 (19)	0.044 (2)	0.0238 (16)	−0.0092 (16)	−0.0055 (14)	0.0092 (14)
O2	0.0270 (18)	0.064 (3)	0.0303 (19)	0.0011 (17)	0.0068 (15)	0.0078 (17)
O3	0.0199 (15)	0.061 (2)	0.0274 (17)	−0.0163 (15)	−0.0040 (13)	−0.0028 (15)
O4	0.0268 (17)	0.075 (3)	0.0185 (15)	−0.0250 (17)	−0.0004 (13)	−0.0012 (16)
O5	0.074 (3)	0.0266 (17)	0.0225 (16)	−0.0142 (17)	−0.0080 (17)	−0.0003 (13)
O6	0.058 (2)	0.0306 (17)	0.0222 (16)	−0.0141 (16)	−0.0143 (15)	0.0071 (13)
O7	0.055 (2)	0.061 (2)	0.088 (3)	−0.0018 (16)	0.0304 (19)	0.0251 (19)
O8	0.048 (2)	0.0333 (19)	0.041 (2)	−0.0115 (16)	0.0176 (17)	−0.0007 (15)
O9	0.055 (2)	0.061 (2)	0.088 (3)	−0.0018 (16)	0.0304 (19)	0.0251 (19)
N1	0.0174 (16)	0.0268 (17)	0.0193 (16)	−0.0077 (13)	−0.0030 (13)	0.0001 (13)
C1	0.0197 (19)	0.024 (2)	0.022 (2)	−0.0068 (16)	−0.0017 (15)	0.0017 (15)
C2	0.028 (2)	0.030 (2)	0.0179 (19)	−0.0099 (17)	−0.0049 (16)	−0.0011 (16)
C3	0.024 (2)	0.025 (2)	0.0162 (18)	−0.0024 (16)	−0.0005 (15)	0.0042 (15)
C4	0.0172 (19)	0.035 (2)	0.022 (2)	−0.0057 (17)	−0.0003 (16)	0.0045 (17)
C5	0.022 (2)	0.031 (2)	0.026 (2)	−0.0110 (17)	−0.0029 (16)	0.0014 (17)
C6	0.033 (2)	0.029 (2)	0.017 (2)	−0.0045 (18)	0.0037 (17)	−0.0004 (16)
C7	0.0196 (19)	0.033 (2)	0.025 (2)	−0.0129 (17)	−0.0041 (16)	0.0032 (17)
C8	0.028 (2)	0.023 (2)	0.0189 (19)	−0.0052 (16)	−0.0027 (16)	0.0009 (15)
O10	0.037 (4)	0.042 (4)	0.072 (6)	−0.010 (3)	−0.013 (4)	0.009 (4)

Geometric parameters (Å, º) top

Ce—N1	2.684 (3)	O8—H8B	0.8600
Ce—O1ⁱ	2.409 (4)	O9—H9B	0.8400
Ce—O3ⁱⁱ	2.505 (3)	O9—H9A	0.9900
Ce—O4	2.511 (3)	O10—H10A	0.8400
Ce—O5	2.508 (3)	O10—H10B	0.9400
Ce—O6ⁱⁱⁱ	2.515 (3)	N1—C5	1.338 (5)
Ce—O7	2.568 (5)	N1—C1	1.343 (6)
Ce—O8	2.515 (4)	C1—C4	1.386 (6)
Ce—O9	2.582 (5)	C1—C7	1.498 (6)
O1—C6	1.268 (6)	C2—C3	1.385 (7)
O2—C6	1.244 (7)	C2—C5	1.390 (6)
O3—C7	1.245 (6)	C3—C6	1.517 (6)
O4—C7	1.268 (5)	C3—C4	1.383 (6)
O5—C8	1.248 (5)	C8—C8ⁱⁱⁱ	1.543 (5)
O6—C8	1.253 (5)	C2—H2A	0.9300
O7—H7B	0.8300	C4—H4A	0.9300
O7—H7A	0.8600	C5—H5A	0.9300
O8—H8A	0.9200

O4—Ce—O5	74.74 (12)	Ce—O5—C8	121.3 (3)
O4—Ce—O7	142.54 (15)	Ceⁱⁱⁱ—O6—C8	120.9 (3)
O4—Ce—O8	75.62 (14)	Ce—O7—H7B	105.00
O4—Ce—O9	130.01 (15)	H7A—O7—H7B	99.00
O4—Ce—N1	61.02 (10)	Ce—O7—H7A	96.00
O3ⁱⁱ—Ce—O4	137.32 (10)	Ce—O8—H8A	127.00
O1ⁱ—Ce—O4	94.76 (13)	H8A—O8—H8B	113.00
O4—Ce—O6ⁱⁱⁱ	70.50 (13)	Ce—O8—H8B	119.00
O5—Ce—O7	84.31 (15)	Ce—O9—H9A	120.00
O5—Ce—O8	78.05 (12)	H9A—O9—H9B	96.00
O5—Ce—O9	67.22 (15)	Ce—O9—H9B	107.00
O5—Ce—N1	130.72 (12)	H10A—O10—H10B	112.00
O3ⁱⁱ—Ce—O5	141.57 (12)	Ce—N1—C5	123.6 (3)
O1ⁱ—Ce—O5	132.71 (11)	Ce—N1—C1	118.7 (2)
O5—Ce—O6ⁱⁱⁱ	64.05 (10)	C1—N1—C5	117.1 (3)
O7—Ce—O8	130.23 (15)	N1—C1—C4	122.5 (4)
O7—Ce—O9	64.30 (16)	N1—C1—C7	115.4 (4)
O7—Ce—N1	144.66 (14)	C4—C1—C7	122.1 (4)
O3ⁱⁱ—Ce—O7	76.31 (14)	C3—C2—C5	118.1 (4)
O1ⁱ—Ce—O7	76.97 (15)	C2—C3—C6	121.4 (4)
O6ⁱⁱⁱ—Ce—O7	72.47 (15)	C4—C3—C6	120.3 (4)
O8—Ce—O9	65.94 (15)	C2—C3—C4	118.3 (4)
O8—Ce—N1	71.24 (12)	C1—C4—C3	119.8 (4)
O3ⁱⁱ—Ce—O8	89.53 (13)	N1—C5—C2	124.1 (4)
O1ⁱ—Ce—O8	144.86 (12)	O1—C6—O2	127.1 (4)
O6ⁱⁱⁱ—Ce—O8	134.19 (12)	O2—C6—C3	116.8 (4)
O9—Ce—N1	127.54 (14)	O1—C6—C3	116.0 (4)
O3ⁱⁱ—Ce—O9	74.47 (14)	O4—C7—C1	116.2 (4)
O1ⁱ—Ce—O9	134.92 (15)	O3—C7—C1	119.4 (4)
O6ⁱⁱⁱ—Ce—O9	116.36 (14)	O3—C7—O4	124.4 (4)
O3ⁱⁱ—Ce—N1	76.35 (10)	O5—C8—O6	126.7 (4)
O1ⁱ—Ce—N1	74.55 (11)	O5—C8—C8ⁱⁱⁱ	116.7 (4)
O6ⁱⁱⁱ—Ce—N1	114.97 (11)	O6—C8—C8ⁱⁱⁱ	116.6 (4)
O1ⁱ—Ce—O3ⁱⁱ	74.72 (12)	C5—C2—H2A	121.00
O3ⁱⁱ—Ce—O6ⁱⁱⁱ	136.22 (12)	C3—C2—H2A	121.00
O1ⁱ—Ce—O6ⁱⁱⁱ	68.95 (11)	C1—C4—H4A	120.00
Ceⁱ—O1—C6	138.2 (3)	C3—C4—H4A	120.00
Ce^iv—O3—C7	140.1 (3)	N1—C5—H5A	118.00
Ce—O4—C7	127.9 (3)	C2—C5—H5A	118.00

O5—Ce—O4—C7	158.0 (4)	N1—Ce—O1ⁱ—C6ⁱ	73.5 (5)
O7—Ce—O4—C7	−143.7 (4)	O4—Ce—O6ⁱⁱⁱ—C8ⁱⁱⁱ	−87.9 (4)
O8—Ce—O4—C7	76.7 (4)	O5—Ce—O6ⁱⁱⁱ—C8ⁱⁱⁱ	−5.9 (3)
O9—Ce—O4—C7	116.9 (4)	O7—Ce—O6ⁱⁱⁱ—C8ⁱⁱⁱ	86.3 (4)
N1—Ce—O4—C7	0.5 (4)	O8—Ce—O6ⁱⁱⁱ—C8ⁱⁱⁱ	−43.3 (4)
O3ⁱⁱ—Ce—O4—C7	3.6 (5)	O9—Ce—O6ⁱⁱⁱ—C8ⁱⁱⁱ	37.9 (4)
O1ⁱ—Ce—O4—C7	−68.9 (4)	N1—Ce—O6ⁱⁱⁱ—C8ⁱⁱⁱ	−130.9 (3)
O6ⁱⁱⁱ—Ce—O4—C7	−134.6 (4)	Ceⁱ—O1—C6—O2	−76.7 (7)
O4—Ce—O5—C8	80.8 (4)	Ceⁱ—O1—C6—C3	101.7 (5)
O7—Ce—O5—C8	−67.9 (4)	Ce^iv—O3—C7—O4	−12.4 (8)
O8—Ce—O5—C8	158.9 (4)	Ce^iv—O3—C7—C1	168.6 (3)
O9—Ce—O5—C8	−132.4 (4)	Ce—O4—C7—O3	−174.5 (3)
N1—Ce—O5—C8	106.9 (4)	Ce—O4—C7—C1	4.5 (6)
O3ⁱⁱ—Ce—O5—C8	−127.4 (4)	Ce—O5—C8—O6	174.3 (4)
O1ⁱ—Ce—O5—C8	−1.5 (5)	Ce—O5—C8—C8ⁱⁱⁱ	−4.7 (6)
O6ⁱⁱⁱ—Ce—O5—C8	5.4 (4)	Ceⁱⁱⁱ—O6—C8—O5	175.0 (4)
O4—Ce—N1—C1	−6.1 (3)	Ceⁱⁱⁱ—O6—C8—C8ⁱⁱⁱ	−6.0 (5)
O4—Ce—N1—C5	−176.6 (4)	Ce—N1—C1—C4	−169.4 (3)
O5—Ce—N1—C1	−35.2 (4)	Ce—N1—C1—C7	10.5 (5)
O5—Ce—N1—C5	154.3 (3)	C5—N1—C1—C4	1.7 (6)
O7—Ce—N1—C1	135.9 (3)	C5—N1—C1—C7	−178.4 (4)
O7—Ce—N1—C5	−34.6 (5)	Ce—N1—C5—C2	168.0 (3)
O8—Ce—N1—C1	−89.7 (3)	C1—N1—C5—C2	−2.7 (7)
O8—Ce—N1—C5	99.8 (4)	N1—C1—C4—C3	1.0 (6)
O9—Ce—N1—C1	−126.2 (3)	C7—C1—C4—C3	−178.8 (4)
O9—Ce—N1—C5	63.3 (4)	N1—C1—C7—O3	169.2 (4)
O3ⁱⁱ—Ce—N1—C1	176.1 (3)	N1—C1—C7—O4	−9.8 (6)
O3ⁱⁱ—Ce—N1—C5	5.6 (3)	C4—C1—C7—O3	−11.0 (6)
O1ⁱ—Ce—N1—C1	98.5 (3)	C4—C1—C7—O4	170.0 (4)
O1ⁱ—Ce—N1—C5	−72.0 (3)	C5—C2—C3—C4	2.0 (6)
O6ⁱⁱⁱ—Ce—N1—C1	41.2 (3)	C5—C2—C3—C6	−177.4 (4)
O6ⁱⁱⁱ—Ce—N1—C5	−129.3 (3)	C3—C2—C5—N1	0.9 (7)
O4—Ce—O3ⁱⁱ—C7ⁱⁱ	−172.6 (4)	C2—C3—C4—C1	−2.8 (7)
O5—Ce—O3ⁱⁱ—C7ⁱⁱ	49.5 (6)	C6—C3—C4—C1	176.5 (4)
O7—Ce—O3ⁱⁱ—C7ⁱⁱ	−12.4 (5)	C2—C3—C6—O1	27.1 (6)
O8—Ce—O3ⁱⁱ—C7ⁱⁱ	119.4 (5)	C2—C3—C6—O2	−154.4 (5)
O9—Ce—O3ⁱⁱ—C7ⁱⁱ	54.3 (5)	C4—C3—C6—O1	−152.3 (4)
N1—Ce—O3ⁱⁱ—C7ⁱⁱ	−169.8 (5)	C4—C3—C6—O2	26.3 (6)
O4—Ce—O1ⁱ—C6ⁱ	131.6 (5)	O5—C8—C8ⁱⁱⁱ—O5ⁱⁱⁱ	−180.0 (5)
O5—Ce—O1ⁱ—C6ⁱ	−154.8 (4)	O5—C8—C8ⁱⁱⁱ—O6ⁱⁱⁱ	−0.9 (6)
O7—Ce—O1ⁱ—C6ⁱ	−85.4 (5)	O6—C8—C8ⁱⁱⁱ—O5ⁱⁱⁱ	0.9 (6)
O8—Ce—O1ⁱ—C6ⁱ	60.0 (6)	O6—C8—C8ⁱⁱⁱ—O6ⁱⁱⁱ	180.0 (4)
O9—Ce—O1ⁱ—C6ⁱ	−54.6 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱⁱ	0.86	2.03	2.879 (6)	171.00
O7—H7B···O10^v	0.83	1.84	2.569 (10)	146.00
O8—H8A···O6^vi	0.92	2.00	2.910 (5)	170.00
O8—H8B···O2^vii	0.86	1.84	2.655 (6)	159.00
O9—H9A···O6^vi	0.99	2.01	2.987 (6)	169.00
O9—H9B···O10	0.84	1.93	2.440 (10)	118.00
O10—H10A···O5ⁱⁱ	0.84	2.12	2.844 (9)	143.00
O10—H10A···O8ⁱⁱ	0.84	2.39	2.913 (10)	121.00
O10—H10B···O9^viii	0.94	1.63	2.501 (11)	153.00
C5—H5A···O3ⁱⁱ	0.93	2.46	3.131 (5)	129

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

Experimental details

Crystal data
Chemical formula	[Ce₂(C₇H₃NO₄)₂(C₂O₄)(H₂O)₆]·H₂O
M_r	824.58
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	6.4160 (5), 6.6486 (6), 13.9920 (12)
α, β, γ (°)	89.917 (1), 85.588 (1), 73.676 (1)
V (Å³)	570.98 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	4.04
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.639, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	6072, 2664, 2416
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.656

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.081, 1.10
No. of reflections	2664
No. of parameters	177
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.75, −2.70

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top

Ce—N1	2.684 (3)	Ce—O6ⁱⁱⁱ	2.515 (3)
Ce—O1ⁱ	2.409 (4)	Ce—O7	2.568 (5)
Ce—O3ⁱⁱ	2.505 (3)	Ce—O8	2.515 (4)
Ce—O4	2.511 (3)	Ce—O9	2.582 (5)
Ce—O5	2.508 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱⁱ	0.86	2.03	2.879 (6)	171.00
O7—H7B···O10^iv	0.83	1.84	2.569 (10)	146.00
O8—H8A···O6^v	0.92	2.00	2.910 (5)	170.00
O8—H8B···O2^vi	0.86	1.84	2.655 (6)	159.00
O9—H9A···O6^v	0.99	2.01	2.987 (6)	169.00
O9—H9B···O10	0.84	1.93	2.440 (10)	118.00
O10—H10A···O5ⁱⁱ	0.84	2.12	2.844 (9)	143.00
O10—H10A···O8ⁱⁱ	0.84	2.39	2.913 (10)	121.00
O10—H10B···O9^vii	0.94	1.63	2.501 (11)	153.00
C5—H5A···O3ⁱⁱ	0.93	2.46	3.131 (5)	129.00

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

Acknowledgements

This work was supported financially by Yuanpei University, Taiwan.

References

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