Poly[(μ4-benzene-1,3,5-tricarboxyl­ato)bis­(N,N-dimethyl­formamide)­cerium(III)]

Li, Z.; Liu, K.

doi:10.1107/S160053681102277X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1020

doi:10.1107/S160053681102277X

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Poly[(μ₄-benzene-1,3,5-tricarboxylato)bis(N,N-dimethylformamide)cerium(III)]

Zhongyue Li ^a ^* and Kun Liu ^a

^aThe Department of Physics–Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China
^*Correspondence e-mail: lizhongyue@hpu.edu.cn

(Received 3 June 2011; accepted 13 June 2011; online 6 July 2011)

The asymmetric unit of the title rare earth coordination polymer, [Ce(C₉H₃O₆)(C₃H₇NO)₂]_n, contains one eight-coordinated Ce³⁺ ion, one benzene-1,3,5-tricarboxylate (BTC) ligand and two coordinated N,N-dimethylformamide (DMF) molecules. The Ce³⁺ ion is coordinated by six O atoms from four carboxylate groups of the BTC ligands and by two O atoms from two terminal DMF molecules.

Related literature

Metal-organic framework (MOF) design and construction is currently a flourishing field of research owing to the intriguing molecular topologies and the potentially exploitable adsorption, catalytic, fluorescence, and magnetic properties, see: Chen et al. (2006 ); Serre et al. (2007 ); Zhang et al. (2007 ). As functional metal centers, rare earth metals are attracting increasing attention from synthesis chemists for their coordination properties and special chemical characteristics arising from 4f electrons and their propensity to form isostructural complexes, see: Thirumurugan et al. (2004 ); Long et al. (2001 ).

Experimental

Crystal data

[Ce(C₉H₃O₆)(C₃H₇NO)₂]
M_r = 493.43
Monoclinic, P 2₁ /n
a = 10.6994 (11) Å
b = 13.6773 (14) Å
c = 12.1961 (13) Å
β = 101.574 (2)°
V = 1748.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.65 mm⁻¹
T = 298 K
0.8 × 0.6 × 0.5 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.226, T_max = 0.351
9223 measured reflections
3087 independent reflections
2516 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.076
S = 1.02
3087 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 1.14 e Å⁻³
Δρ_min = −1.05 e Å⁻³

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681102277X/qm2010sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102277X/qm2010Isup2.hkl

checkCIF report

Related literature top

Metal-organic framework (MOF) design and construction is currently a flourishing field of research owing to the intriguing molecular topologies and the potentially exploitable adsorption, catalytic, fluorescence, and magnetic properties, see: Chen et al. (2006); Serre et al. (2007); Zhang et al. (2007). As functional metal centers, rare earth metals are attracting increasing attention from synthesis chemists for their coordination properties and special chemical characteristics arising from 4f electrons and their propensity to form isostructural complexes, see: Thirumurugan et al.( 2004); Long et al. (2001).

Experimental top

All reagents were of analytical grade. A mixture of cerium nitrate (40 mg, 0.10 mmol) and µ₃-benzene-1,3,5-tricarboxylate acid(H₃BTC) (10 mg, 0.05 mmol) was dissolved in N,N'-dimethylformamide (DMF) (10 mL) and isopropanol (2 mL) at room temperature, two drops of triethylamine was added, then some nitric acid(2M) was added utill the solution is clear. This mixture was placed in a 20 mL test tube. Then a small vial containing triethylamine (0.1 mL) and DMF (1.5 mL) was put in the test tube. The test tube was left undisturbed at room temprature for 15 days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Coordination environment of Ce in the compound with nonhydrogen atoms represented by thermal ellipsoids draw at 30 % probability level.

Poly[(µ₄-benzene-1,3,5-tricarboxylato)bis(N,N- dimethylformamide)cerium(III)] top

Crystal data top

[Ce(C₉H₃O₆)(C₃H₇NO)₂]	Z = 4
M_r = 493.43	F(000) = 972
Monoclinic, P2₁/n	D_x = 1.874 Mg m⁻³
a = 10.6994 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.6773 (14) Å	µ = 2.65 mm⁻¹
c = 12.1961 (13) Å	T = 298 K
β = 101.574 (2)°	Rod, colorless
V = 1748.5 (3) Å³	0.8 × 0.6 × 0.5 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3087 independent reflections
Radiation source: fine-focus sealed tube	2516 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→12
T_min = 0.226, T_max = 0.351	k = −16→16
9223 measured reflections	l = −13→14

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) = 0.076	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0173P)²] where P = (F_o² + 2F_c²)/3
3087 reflections	(Δ/σ)_max = 0.008
239 parameters	Δρ_max = 1.14 e Å⁻³
0 restraints	Δρ_min = −1.05 e Å⁻³

Crystal data top

[Ce(C₉H₃O₆)(C₃H₇NO)₂]	V = 1748.5 (3) Å³
M_r = 493.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.6994 (11) Å	µ = 2.65 mm⁻¹
b = 13.6773 (14) Å	T = 298 K
c = 12.1961 (13) Å	0.8 × 0.6 × 0.5 mm
β = 101.574 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3087 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2516 reflections with I > 2σ(I)
T_min = 0.226, T_max = 0.351	R_int = 0.059
9223 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	Δρ_max = 1.14 e Å⁻³
3087 reflections	Δρ_min = −1.05 e Å⁻³
239 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	0.62306 (3)	1.03609 (3)	0.39566 (3)	0.01481 (11)
C1	0.6993 (6)	0.9240 (4)	0.6584 (5)	0.0170 (15)
C2	0.8218 (6)	0.8724 (4)	0.7133 (6)	0.0188 (15)
C3	0.9313 (6)	0.8882 (4)	0.6695 (5)	0.0189 (15)
H3	0.9285	0.9309	0.6096	0.023*
C4	1.0448 (6)	0.8403 (4)	0.7153 (5)	0.0174 (15)
C5	1.0469 (6)	0.7730 (4)	0.7994 (5)	0.0179 (15)
H5	1.1210	0.7378	0.8264	0.021*
C6	0.9388 (6)	0.7571 (4)	0.8446 (5)	0.0178 (15)
C7	0.8280 (6)	0.8097 (4)	0.8014 (5)	0.0206 (15)
H7	0.7567	0.8018	0.8334	0.025*
C8	0.9393 (6)	0.6846 (5)	0.9368 (6)	0.0184 (15)
C9	0.8386 (6)	1.1342 (4)	0.3310 (6)	0.0189 (15)
C10	0.8855 (7)	0.8868 (5)	0.3589 (7)	0.0347 (19)
H10	0.9423	0.8752	0.4260	0.042*
C11	0.8492 (8)	0.9013 (7)	0.1589 (7)	0.068 (3)
H11A	0.7749	0.9368	0.1690	0.102*
H11B	0.8236	0.8408	0.1212	0.102*
H11C	0.8959	0.9396	0.1148	0.102*
C12	1.0614 (7)	0.8523 (6)	0.2683 (8)	0.061 (3)
H12A	1.1029	0.9018	0.2327	0.091*
H12B	1.0622	0.7915	0.2290	0.091*
H12C	1.1057	0.8444	0.3445	0.091*
C13	0.4387 (8)	0.9287 (5)	0.1597 (7)	0.038 (2)
H13	0.3729	0.9378	0.1982	0.046*
C14	0.2840 (8)	0.8444 (6)	0.0187 (8)	0.068 (3)
H14A	0.2850	0.7743	0.0206	0.102*
H14B	0.2575	0.8662	−0.0573	0.102*
H14C	0.2255	0.8684	0.0627	0.102*
C15	0.5082 (8)	0.8594 (6)	0.0012 (7)	0.053 (2)
H15A	0.5838	0.8965	0.0303	0.080*
H15B	0.4775	0.8761	−0.0759	0.080*
H15C	0.5278	0.7909	0.0072	0.080*
N1	0.9291 (6)	0.8814 (4)	0.2665 (6)	0.0356 (16)
N2	0.4117 (6)	0.8815 (4)	0.0643 (5)	0.0374 (16)
O1	0.7104 (4)	0.9890 (3)	0.5883 (4)	0.0250 (11)
O2	0.5978 (4)	0.9001 (3)	0.6867 (4)	0.0263 (11)
O3	0.8522 (4)	1.1009 (3)	0.4277 (4)	0.0268 (11)
O4	0.7289 (4)	1.1428 (3)	0.2671 (4)	0.0289 (12)
O5	0.5116 (4)	0.8900 (3)	0.4415 (4)	0.0241 (11)
O6	0.6335 (4)	1.1973 (3)	0.4976 (4)	0.0270 (12)
O7	0.7738 (5)	0.9063 (3)	0.3633 (4)	0.0406 (14)
O8	0.5433 (4)	0.9618 (4)	0.2023 (4)	0.0342 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ce1	0.01096 (19)	0.01648 (19)	0.0170 (2)	−0.00043 (18)	0.00285 (13)	−0.00011 (19)
C1	0.012 (4)	0.018 (4)	0.019 (4)	0.001 (3)	−0.001 (3)	−0.005 (3)
C2	0.012 (4)	0.017 (4)	0.026 (4)	0.001 (3)	0.000 (3)	−0.002 (3)
C3	0.020 (4)	0.016 (3)	0.021 (4)	−0.001 (3)	0.004 (3)	0.006 (3)
C4	0.020 (4)	0.011 (3)	0.021 (4)	−0.001 (3)	0.005 (3)	0.002 (3)
C5	0.010 (4)	0.017 (4)	0.025 (4)	0.000 (3)	−0.001 (3)	0.004 (3)
C6	0.016 (4)	0.015 (4)	0.022 (4)	0.002 (3)	0.003 (3)	0.003 (3)
C7	0.016 (4)	0.026 (4)	0.021 (4)	0.001 (3)	0.005 (3)	0.005 (3)
C8	0.013 (4)	0.016 (4)	0.026 (4)	−0.005 (3)	0.003 (3)	−0.002 (3)
C9	0.015 (4)	0.015 (4)	0.029 (4)	−0.004 (3)	0.009 (3)	0.000 (3)
C10	0.032 (5)	0.024 (4)	0.047 (6)	0.007 (4)	0.004 (4)	−0.011 (4)
C11	0.068 (7)	0.096 (8)	0.037 (6)	0.023 (6)	0.006 (5)	−0.025 (6)
C12	0.032 (5)	0.060 (6)	0.097 (8)	0.011 (4)	0.029 (5)	−0.020 (6)
C13	0.044 (5)	0.041 (5)	0.029 (5)	0.003 (4)	0.004 (4)	0.001 (4)
C14	0.069 (7)	0.071 (7)	0.053 (7)	−0.018 (5)	−0.014 (5)	−0.015 (5)
C15	0.075 (7)	0.043 (5)	0.039 (6)	−0.004 (4)	0.006 (5)	−0.006 (4)
N1	0.029 (4)	0.030 (4)	0.049 (5)	0.005 (3)	0.011 (3)	−0.013 (3)
N2	0.043 (4)	0.040 (4)	0.024 (4)	−0.005 (3)	−0.004 (3)	−0.005 (3)
O1	0.023 (3)	0.024 (3)	0.025 (3)	0.002 (2)	−0.002 (2)	0.010 (2)
O2	0.012 (3)	0.039 (3)	0.029 (3)	0.003 (2)	0.005 (2)	0.008 (2)
O3	0.021 (3)	0.036 (3)	0.026 (3)	−0.002 (2)	0.008 (2)	0.004 (2)
O4	0.012 (3)	0.042 (3)	0.032 (3)	0.003 (2)	0.003 (2)	0.009 (2)
O5	0.019 (3)	0.019 (3)	0.035 (3)	−0.004 (2)	0.007 (2)	−0.007 (2)
O6	0.030 (3)	0.025 (3)	0.030 (3)	−0.008 (2)	0.016 (2)	−0.007 (2)
O7	0.028 (3)	0.036 (3)	0.060 (4)	0.003 (2)	0.015 (3)	−0.012 (3)
O8	0.031 (3)	0.036 (3)	0.031 (3)	0.002 (3)	−0.002 (2)	−0.011 (3)

Geometric parameters (Å, º) top

Ce1—O1	2.434 (4)	C9—O3	1.245 (8)
Ce1—O5	2.448 (4)	C9—O4	1.278 (7)
Ce1—O7	2.483 (5)	C9—C4ⁱⁱⁱ	1.511 (8)
Ce1—O6	2.522 (4)	C10—O7	1.236 (7)
Ce1—O2ⁱ	2.531 (4)	C10—N1	1.306 (9)
Ce1—O8	2.553 (5)	C10—H10	0.9300
Ce1—O3	2.562 (4)	C11—N1	1.441 (10)
Ce1—O4	2.565 (4)	C11—H11A	0.9600
Ce1—O5ⁱ	2.862 (4)	C11—H11B	0.9600
Ce1—C9	2.910 (6)	C11—H11C	0.9600
Ce1—C8ⁱⁱ	3.049 (6)	C12—N1	1.466 (8)
Ce1—Ce1ⁱ	4.1322 (7)	C12—H12A	0.9600
C1—O2	1.247 (7)	C12—H12B	0.9600
C1—O1	1.256 (7)	C12—H12C	0.9600
C1—C2	1.520 (8)	C13—O8	1.222 (8)
C2—C7	1.367 (8)	C13—N2	1.311 (9)
C2—C3	1.399 (8)	C13—H13	0.9300
C3—C4	1.394 (8)	C14—N2	1.459 (9)
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.374 (8)	C14—H14B	0.9600
C4—C9ⁱⁱⁱ	1.511 (8)	C14—H14C	0.9600
C5—C6	1.394 (8)	C15—N2	1.438 (9)
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.397 (8)	C15—H15B	0.9600
C6—C8	1.498 (8)	C15—H15C	0.9600
C7—H7	0.9300	O2—Ce1ⁱ	2.531 (4)
C8—O6^iv	1.236 (7)	O5—C8^vi	1.276 (7)
C8—O5^v	1.276 (7)	O5—Ce1ⁱ	2.862 (4)
C8—Ce1^iv	3.049 (6)	O6—C8ⁱⁱ	1.236 (7)

O1—Ce1—O5	70.96 (14)	C4—C3—H3	119.9
O1—Ce1—O7	80.11 (16)	C2—C3—H3	119.9
O5—Ce1—O7	79.29 (15)	C5—C4—C3	119.8 (6)
O1—Ce1—O6	77.59 (14)	C5—C4—C9ⁱⁱⁱ	122.9 (6)
O5—Ce1—O6	125.18 (13)	C3—C4—C9ⁱⁱⁱ	117.3 (6)
O7—Ce1—O6	137.51 (16)	C4—C5—C6	120.6 (6)
O1—Ce1—O2ⁱ	128.43 (14)	C4—C5—H5	119.7
O5—Ce1—O2ⁱ	85.03 (14)	C6—C5—H5	119.7
O7—Ce1—O2ⁱ	140.18 (16)	C5—C6—C7	118.7 (6)
O6—Ce1—O2ⁱ	80.79 (15)	C5—C6—C8	121.4 (5)
O1—Ce1—O8	141.15 (15)	C7—C6—C8	119.9 (5)
O5—Ce1—O8	78.37 (15)	C2—C7—C6	121.5 (6)
O7—Ce1—O8	71.08 (16)	C2—C7—H7	119.2
O6—Ce1—O8	140.98 (15)	C6—C7—H7	119.2
O2ⁱ—Ce1—O8	70.00 (14)	O6^iv—C8—O5^v	122.6 (6)
O1—Ce1—O3	76.95 (14)	O6^iv—C8—C6	119.1 (6)
O5—Ce1—O3	137.95 (14)	O5^v—C8—C6	118.3 (5)
O7—Ce1—O3	68.89 (15)	O6^iv—C8—Ce1^iv	53.7 (3)
O6—Ce1—O3	71.07 (14)	O5^v—C8—Ce1^iv	69.4 (3)
O2ⁱ—Ce1—O3	136.88 (14)	C6—C8—Ce1^iv	167.4 (4)
O8—Ce1—O3	114.27 (14)	O3—C9—O4	122.0 (6)
O1—Ce1—O4	127.54 (14)	O3—C9—C4ⁱⁱⁱ	119.4 (6)
O5—Ce1—O4	153.98 (15)	O4—C9—C4ⁱⁱⁱ	118.5 (6)
O7—Ce1—O4	85.95 (15)	O3—C9—Ce1	61.5 (3)
O6—Ce1—O4	79.79 (14)	O4—C9—Ce1	61.7 (3)
O2ⁱ—Ce1—O4	93.02 (14)	C4ⁱⁱⁱ—C9—Ce1	165.2 (4)
O8—Ce1—O4	76.61 (15)	O7—C10—N1	124.5 (8)
O3—Ce1—O4	50.97 (14)	O7—C10—H10	117.8
O1—Ce1—O5ⁱ	64.72 (13)	N1—C10—H10	117.8
O5—Ce1—O5ⁱ	78.09 (14)	N1—C11—H11A	109.5
O7—Ce1—O5ⁱ	142.78 (15)	N1—C11—H11B	109.5
O6—Ce1—O5ⁱ	47.78 (12)	H11A—C11—H11B	109.5
O2ⁱ—Ce1—O5ⁱ	66.03 (13)	N1—C11—H11C	109.5
O8—Ce1—O5ⁱ	131.33 (13)	H11A—C11—H11C	109.5
O3—Ce1—O5ⁱ	111.80 (13)	H11B—C11—H11C	109.5
O4—Ce1—O5ⁱ	124.65 (13)	N1—C12—H12A	109.5
O1—Ce1—C9	102.23 (17)	N1—C12—H12B	109.5
O5—Ce1—C9	152.48 (15)	H12A—C12—H12B	109.5
O7—Ce1—C9	73.23 (16)	N1—C12—H12C	109.5
O6—Ce1—C9	76.78 (15)	H12A—C12—H12C	109.5
O2ⁱ—Ce1—C9	117.46 (17)	H12B—C12—H12C	109.5
O8—Ce1—C9	93.97 (17)	O8—C13—N2	125.4 (7)
O3—Ce1—C9	25.29 (16)	O8—C13—H13	117.3
O4—Ce1—C9	26.02 (16)	N2—C13—H13	117.3
O5ⁱ—Ce1—C9	124.18 (15)	N2—C14—H14A	109.5
O1—Ce1—C8ⁱⁱ	67.83 (15)	N2—C14—H14B	109.5
O5—Ce1—C8ⁱⁱ	102.05 (15)	H14A—C14—H14B	109.5
O7—Ce1—C8ⁱⁱ	145.03 (17)	N2—C14—H14C	109.5
O6—Ce1—C8ⁱⁱ	23.26 (14)	H14A—C14—H14C	109.5
O2ⁱ—Ce1—C8ⁱⁱ	73.98 (16)	H14B—C14—H14C	109.5
O8—Ce1—C8ⁱⁱ	143.82 (16)	N2—C15—H15A	109.5
O3—Ce1—C8ⁱⁱ	89.90 (15)	N2—C15—H15B	109.5
O4—Ce1—C8ⁱⁱ	102.32 (16)	H15A—C15—H15B	109.5
O5ⁱ—Ce1—C8ⁱⁱ	24.66 (13)	N2—C15—H15C	109.5
C9—Ce1—C8ⁱⁱ	99.56 (17)	H15A—C15—H15C	109.5
O1—Ce1—Ce1ⁱ	60.72 (10)	H15B—C15—H15C	109.5
O5—Ce1—Ce1ⁱ	42.67 (9)	C10—N1—C11	121.7 (7)
O7—Ce1—Ce1ⁱ	116.20 (11)	C10—N1—C12	120.9 (7)
O6—Ce1—Ce1ⁱ	82.87 (9)	C11—N1—C12	117.3 (6)
O2ⁱ—Ce1—Ce1ⁱ	70.56 (10)	C13—N2—C15	121.6 (7)
O8—Ce1—Ce1ⁱ	109.76 (11)	C13—N2—C14	122.2 (7)
O3—Ce1—Ce1ⁱ	134.19 (10)	C15—N2—C14	116.2 (7)
O4—Ce1—Ce1ⁱ	157.85 (10)	C1—O1—Ce1	140.8 (4)
O5ⁱ—Ce1—Ce1ⁱ	35.43 (8)	C1—O2—Ce1ⁱ	126.5 (4)
C9—Ce1—Ce1ⁱ	156.13 (14)	C9—O3—Ce1	93.2 (4)
C8ⁱⁱ—Ce1—Ce1ⁱ	59.61 (12)	C9—O4—Ce1	92.3 (4)
O2—C1—O1	125.5 (6)	C8^vi—O5—Ce1	164.1 (4)
O2—C1—C2	118.6 (6)	C8^vi—O5—Ce1ⁱ	85.9 (3)
O1—C1—C2	115.9 (5)	Ce1—O5—Ce1ⁱ	101.90 (14)
C7—C2—C3	119.0 (6)	C8ⁱⁱ—O6—Ce1	103.0 (4)
C7—C2—C1	122.6 (5)	C10—O7—Ce1	145.6 (4)
C3—C2—C1	118.3 (6)	C13—O8—Ce1	130.4 (5)
C4—C3—C2	120.2 (6)

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

Experimental details

Crystal data
Chemical formula	[Ce(C₉H₃O₆)(C₃H₇NO)₂]
M_r	493.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.6994 (11), 13.6773 (14), 12.1961 (13)
β (°)	101.574 (2)
V (Å³)	1748.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.65
Crystal size (mm)	0.8 × 0.6 × 0.5

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.226, 0.351
No. of measured, independent and observed [I > 2σ(I)] reflections	9223, 3087, 2516
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.076, 1.02
No. of reflections	3087
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.14, −1.05

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We thank the Open Research Fund of the State Key Laboratory of Inorganic Synthesis and Preparative Chemistry (grant No. 2011–08).

References

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