Poly[triaqua­tris­(μ4-pyridine-3,5-dicarboxyl­ato)dicerium(III)]

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

doi:10.1107/S1600536811000286

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m161-m162

doi:10.1107/S1600536811000286

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Poly[triaquatris(μ₄-pyridine-3,5-dicarboxylato)dicerium(III)]

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

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

(Received 26 December 2010; accepted 4 January 2011; online 15 January 2011)

The asymmetric unit of the title compound, [Ce₂(C₇H₃NO₄)₃(H₂O)₃]_n, contains two Ce^III cations, three pyridine-3,5-dicarboxylate (pyd) anions and three coordinated water molecules. One Ce^III cation is coordinated by seven carboxylate O atoms from six pyd anions and two water molecules in a square-face-capped square-antiprismatic geometry. Another Ce^III cation is coordinated by seven O atoms from six pdy anions and one water molecule in a bicapped trigonal–prismatic geometry. The pdy anions bridge the Ce^III cations, forming the three-dimensional polymeric structure. The crystal structure contains extensive O—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonds. π–π stacking is present in the crystal structure, the shortest centroid–centroid distance between parallel pyridine rings being 3.509 (4) Å.

Related literature

3,5-PydH₂ can be easily deprotonated to the N-donor multidentate anion (pyd²⁻), enabling the ligand to act as a bridge to 3d and/or 4f metal ions, see: Jia et al. (2006 ). For related structures, see: Guo et al. (2009 ); Li (2007 ); Yi et al. (2009 ).

Experimental

Crystal data

[Ce₂(C₇H₃NO₄)₃(H₂O)₃]
M_r = 829.60
Triclinic, $[P \overline 1]$
a = 8.959 (3) Å
b = 9.429 (3) Å
c = 14.582 (4) Å
α = 98.115 (6)°
β = 95.501 (6)°
γ = 105.030 (6)°
V = 1166.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 3.94 mm⁻¹
T = 295 K
0.15 × 0.08 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.756, T_max = 0.975
12583 measured reflections
5586 independent reflections
2847 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.076
S = 0.74
5586 reflections
370 parameters
H-atom parameters not refined
Δρ_max = 1.36 e Å⁻³
Δρ_min = −1.15 e Å⁻³

Table 1
Selected bond lengths (Å)

Ce1—O1ⁱ	2.349 (6)
Ce1—O3	2.773 (5)
Ce1—O4	2.570 (5)
Ce1—O5ⁱⁱ	2.384 (5)
Ce1—O7	2.538 (5)
Ce1—O9	2.538 (5)
Ce1—O11ⁱⁱⁱ	2.405 (5)
Ce1—O13	2.560 (5)
Ce2—O2^iv	2.404 (5)
Ce2—O3	2.594 (5)
Ce2—O6^v	2.431 (5)
Ce2—O7	2.847 (6)
Ce2—O8	2.657 (6)
Ce2—O10^vi	2.526 (5)
Ce2—O12ⁱⁱⁱ	2.444 (5)
Ce2—O14	2.606 (6)
Ce2—O15	2.646 (6)
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y+1, z; (iii) -x, -y+1, -z; (iv) -x+1, -y, -z+1; (v) x+1, y+1, z; (vi) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O13—H13A⋯O4^vii	0.82	2.28	2.901 (7)	132
O13—H13B⋯N1^viii	0.81	1.87	2.659 (9)	164
O14—H14A⋯N2^vi	0.89	2.06	2.802 (9)	140
O14—H14B⋯O10^vi	0.88	2.40	3.031 (9)	129
O15—H15A⋯O10^vi	0.82	2.40	2.853 (9)	115
O15—H15B⋯N3	0.82	2.00	2.815 (9)	174
C8—H8⋯O12^ix	0.93	2.43	3.354 (9)	172
C12—H12⋯O9	0.93	2.57	3.354 (9)	143
C15—H15⋯O7	0.93	2.38	3.258 (9)	157
Symmetry codes: (vi) x+1, y, z; (vii) -x, -y+1, -z+1; (viii) -x+1, -y+1, -z+1; (ix) -x-1, -y, -z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000286/xu5131sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000286/xu5131Isup2.hkl

checkCIF report

Comment top

3,5-PydH₂ can be easily deprotonated to get a O-donors to N-donor multidentate anion (pyd^2-), enabling the ligand to act as a bridge to 3 d and/or 4f metal ions (Jia et al., 2006). Some examples of coordination polymer with 3,5-pydH₂ have been reported (Guo et al., 2009; Li, 2007; Yi et al., 2009).

The asymmetric unit of the title compound contain two independent Ce^III atoms, three pyridine-3,5-dicarboxylate(3,5-pyd) ligands and three coordinated water molecules. One Ce^III atom is coordinated by nine O atoms from six 3,5-pyd groups and two water molecules, forming a square-face capped square antiprism. Another Ce^III atom is coordinated by seven O atoms from six 3,5-pdy groups and one O atom from one water molecule, forming a 4,4'-bicapped trigonal prism. By sharing two carboxylate O atoms via a mono atomic bridging mode, two Ce centers are connected into a binuclear unit(Table 1 and Fig.1).

The crystal structure contains an extensive network of classical O—H···O, O—H···N and weak C—H···O hydrogen bonds(full details and symmetry codes are given in Table 2 and Fig. 2).The π···π stacking interactions are also observed, the centroid-centroid distance between the pyridine rings of unbridging 3,5-pyd is 3.509 (4)Å [Cg5ⁱⁱⁱ···Cg5 (N3/C15—C19)] [symmetry code: -x, 1 - y, -z].

Related literature top

3,5-PydH₂ can be easily deprotonated to the N-donor multidentate anion (pyd^2-), enabling the ligand to act as a bridge to 3d and/or 4f metal ions, see: Jia et al. (2006). For related structures, see: Guo et al. (2009); Li (2007); Yi et al. (2009).

Experimental top

A mixture of Ce(NO₃)₃.6H₂O (0.867 g, 0.2 mmole), 3,5-pydH₂ (0.495 g, 0.3 mmol) and 10 ml H₂O was sealed in a 25 ml teflon-lined bomb at 423 K for 3 days and then cooled to room temperature. Colorless crystals were collected (yield 45%, based on Ce(NO₃)₃).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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. H atoms have been omitted for clarity.[Symmetry codes: (i) x, y + 1, z; (ii)-x, -y, -z + 1; (iii) -x, -y + 1, -z; (iv) x + 1, y, z; (v) x + 1, y + 1, z; (vi) -x + 1, -y, -z + 1.]
	Fig. 2. The molecular packing for the title compound. Hydrogen bonds are shown as dashed lines.

Poly[triaquatris(µ₄-pyridine-3,5-dicarboxylato)dicerium(III)] top

Crystal data top

[Ce₂(C₇H₃NO₄)₃(H₂O)₃]	Z = 2
M_r = 829.60	F(000) = 796
Triclinic, P1	D_x = 2.362 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.959 (3) Å	Cell parameters from 1701 reflections
b = 9.429 (3) Å	θ = 2.5–25.0°
c = 14.582 (4) Å	µ = 3.94 mm⁻¹
α = 98.115 (6)°	T = 295 K
β = 95.501 (6)°	Columnar, colorless
γ = 105.030 (6)°	0.15 × 0.08 × 0.02 mm
V = 1166.4 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5586 independent reflections
Radiation source: fine-focus sealed tube	2847 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
Detector resolution: 9 pixels mm^-1	θ_max = 28.4°, θ_min = 1.4°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −12→12
T_min = 0.756, T_max = 0.975	l = −18→19
12583 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters not refined
S = 0.74	w = 1/[σ²(F_o²) + (0.015P)²] where P = (F_o² + 2F_c²)/3
5586 reflections	(Δ/σ)_max = 0.002
370 parameters	Δρ_max = 1.36 e Å⁻³
0 restraints	Δρ_min = −1.15 e Å⁻³

Crystal data top

[Ce₂(C₇H₃NO₄)₃(H₂O)₃]	γ = 105.030 (6)°
M_r = 829.60	V = 1166.4 (6) Å³
Triclinic, P1	Z = 2
a = 8.959 (3) Å	Mo Kα radiation
b = 9.429 (3) Å	µ = 3.94 mm⁻¹
c = 14.582 (4) Å	T = 295 K
α = 98.115 (6)°	0.15 × 0.08 × 0.02 mm
β = 95.501 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5586 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2847 reflections with I > 2σ(I)
T_min = 0.756, T_max = 0.975	R_int = 0.090
12583 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.076	H-atom parameters not refined
S = 0.74	Δρ_max = 1.36 e Å⁻³
5586 reflections	Δρ_min = −1.15 e Å⁻³
370 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
Ce1	−0.04398 (5)	0.35570 (5)	0.33964 (3)	0.0181 (2)
Ce2	0.35910 (5)	0.23588 (5)	0.22599 (3)	0.0168 (2)
O1	0.2438 (6)	−0.1610 (6)	0.6274 (3)	0.0264 (17)
O2	0.4960 (6)	−0.1188 (6)	0.6760 (3)	0.0237 (17)
O3	0.2578 (5)	0.3334 (5)	0.3765 (3)	0.0215 (17)
O4	0.0764 (6)	0.2234 (5)	0.4572 (3)	0.0229 (17)
O5	−0.1974 (5)	−0.4732 (5)	0.3614 (3)	0.0217 (17)
O6	−0.4502 (6)	−0.5346 (5)	0.3038 (3)	0.0222 (17)
O7	0.0313 (6)	0.1587 (5)	0.2310 (3)	0.0222 (17)
O8	0.1594 (6)	−0.0047 (6)	0.2628 (4)	0.038 (2)
O9	−0.2542 (6)	0.2878 (6)	0.1987 (3)	0.032 (2)
O10	−0.4582 (6)	0.3168 (6)	0.1098 (3)	0.0328 (19)
O11	−0.0774 (6)	0.4892 (6)	−0.2348 (3)	0.032 (2)
O12	−0.2635 (6)	0.5672 (5)	−0.1697 (3)	0.0273 (17)
O13	0.1027 (6)	0.5939 (6)	0.4542 (3)	0.0318 (19)
O14	0.3991 (6)	−0.0037 (6)	0.1307 (4)	0.040 (2)
O15	0.2259 (7)	0.1451 (7)	0.0501 (4)	0.048 (3)
N1	0.6058 (7)	0.2665 (7)	0.5638 (4)	0.022 (2)
N2	−0.3912 (7)	−0.1665 (7)	0.1751 (4)	0.025 (2)
N3	−0.0159 (7)	0.2521 (7)	−0.0258 (4)	0.024 (2)
C1	0.5675 (9)	0.1464 (8)	0.6054 (4)	0.021 (3)
C2	0.4160 (8)	0.0545 (7)	0.5953 (4)	0.014 (2)
C3	0.3002 (8)	0.0911 (7)	0.5431 (4)	0.016 (3)
C4	0.3367 (8)	0.2156 (8)	0.4998 (5)	0.016 (3)
C5	0.4931 (9)	0.2967 (8)	0.5117 (5)	0.022 (3)
C6	0.3835 (10)	−0.0854 (8)	0.6374 (5)	0.022 (3)
C7	0.2161 (9)	0.2597 (8)	0.4410 (5)	0.022 (3)
C8	−0.4043 (9)	−0.2893 (8)	0.2140 (5)	0.026 (3)
C9	−0.2820 (8)	−0.3157 (8)	0.2669 (4)	0.017 (3)
C10	−0.1376 (8)	−0.2142 (8)	0.2774 (5)	0.019 (3)
C11	−0.1195 (8)	−0.0880 (8)	0.2375 (5)	0.016 (2)
C12	−0.2506 (9)	−0.0689 (8)	0.1882 (5)	0.024 (3)
C13	−0.3132 (8)	−0.4542 (8)	0.3137 (5)	0.016 (2)
C14	0.0358 (9)	0.0273 (9)	0.2447 (5)	0.022 (3)
C15	−0.1092 (9)	0.2494 (8)	0.0402 (5)	0.024 (3)
C16	−0.2283 (8)	0.3167 (8)	0.0422 (5)	0.019 (3)
C17	−0.2543 (8)	0.3915 (8)	−0.0296 (5)	0.018 (2)
C18	−0.1586 (8)	0.3997 (8)	−0.0992 (4)	0.015 (2)
C19	−0.0426 (8)	0.3287 (8)	−0.0939 (5)	0.020 (3)
C20	−0.3221 (9)	0.3057 (8)	0.1236 (5)	0.022 (3)
C21	−0.1691 (9)	0.4919 (8)	−0.1739 (5)	0.021 (3)
H1	0.64560	0.12380	0.64250	0.0250*
H3	0.19750	0.03280	0.53670	0.0190*
H5	0.51990	0.37760	0.48090	0.0260*
H8	−0.50090	−0.36000	0.20470	0.0310*
H10	−0.05230	−0.23090	0.31130	0.0220*
H12	−0.23990	0.01760	0.16270	0.0290*
H13A	0.05900	0.65940	0.44730	0.0800*
H13B	0.19210	0.62040	0.44390	0.0800*
H14A	0.42300	−0.08900	0.13360	0.0800*
H14B	0.47800	0.05300	0.10900	0.0800*
H15	−0.09260	0.19820	0.08850	0.0280*
H15A	0.30020	0.16410	0.02050	0.0800*
H15B	0.15980	0.18250	0.03010	0.0800*
H17	−0.33550	0.43610	−0.03150	0.0210*
H19	0.02160	0.33400	−0.14060	0.0250*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ce1	0.0143 (3)	0.0185 (3)	0.0231 (3)	0.0042 (2)	0.0029 (2)	0.0094 (2)
Ce2	0.0132 (3)	0.0182 (3)	0.0212 (3)	0.0055 (2)	0.0018 (2)	0.0091 (2)
O1	0.021 (3)	0.023 (3)	0.035 (3)	−0.002 (3)	0.008 (3)	0.017 (3)
O2	0.021 (3)	0.026 (3)	0.028 (3)	0.010 (3)	−0.001 (2)	0.014 (3)
O3	0.020 (3)	0.028 (3)	0.020 (3)	0.007 (2)	0.005 (2)	0.014 (2)
O4	0.018 (3)	0.031 (3)	0.023 (3)	0.009 (3)	0.003 (2)	0.011 (3)
O5	0.017 (3)	0.018 (3)	0.031 (3)	0.007 (2)	−0.002 (2)	0.007 (2)
O6	0.019 (3)	0.021 (3)	0.029 (3)	0.007 (2)	0.004 (2)	0.009 (2)
O7	0.019 (3)	0.016 (3)	0.031 (3)	0.002 (2)	0.002 (2)	0.008 (2)
O8	0.014 (3)	0.027 (4)	0.075 (5)	0.006 (3)	0.002 (3)	0.016 (3)
O9	0.047 (4)	0.034 (4)	0.017 (3)	0.013 (3)	0.002 (3)	0.005 (3)
O10	0.015 (3)	0.057 (4)	0.028 (3)	0.007 (3)	0.008 (3)	0.015 (3)
O11	0.035 (4)	0.044 (4)	0.027 (3)	0.016 (3)	0.013 (3)	0.022 (3)
O12	0.029 (3)	0.023 (3)	0.037 (3)	0.012 (3)	0.006 (3)	0.019 (3)
O13	0.020 (3)	0.025 (3)	0.050 (4)	0.006 (3)	0.003 (3)	0.007 (3)
O14	0.047 (4)	0.022 (4)	0.059 (4)	0.023 (3)	−0.003 (3)	0.011 (3)
O15	0.057 (4)	0.063 (5)	0.033 (4)	0.041 (4)	−0.010 (3)	0.001 (3)
N1	0.021 (4)	0.019 (4)	0.025 (4)	0.001 (3)	0.001 (3)	0.010 (3)
N2	0.021 (4)	0.019 (4)	0.036 (4)	0.008 (3)	−0.001 (3)	0.011 (3)
N3	0.027 (4)	0.031 (4)	0.019 (4)	0.014 (3)	0.004 (3)	0.007 (3)
C1	0.030 (5)	0.025 (5)	0.006 (4)	0.011 (4)	−0.008 (3)	0.001 (3)
C2	0.019 (4)	0.012 (4)	0.013 (4)	0.006 (3)	0.002 (3)	0.002 (3)
C3	0.008 (4)	0.020 (5)	0.021 (4)	0.002 (3)	0.007 (3)	0.007 (3)
C4	0.014 (4)	0.020 (5)	0.017 (4)	0.005 (3)	0.005 (3)	0.012 (3)
C5	0.022 (5)	0.019 (5)	0.024 (5)	0.004 (4)	0.005 (4)	0.005 (4)
C6	0.035 (6)	0.016 (5)	0.015 (4)	0.012 (4)	−0.003 (4)	0.001 (3)
C7	0.024 (5)	0.020 (5)	0.021 (4)	0.012 (4)	0.002 (4)	−0.005 (4)
C8	0.019 (5)	0.023 (5)	0.032 (5)	0.004 (4)	−0.001 (4)	0.002 (4)
C9	0.017 (4)	0.019 (5)	0.015 (4)	0.008 (4)	0.002 (3)	0.001 (3)
C10	0.010 (4)	0.025 (5)	0.024 (4)	0.008 (4)	0.004 (3)	0.007 (4)
C11	0.017 (4)	0.018 (4)	0.012 (4)	0.003 (3)	0.000 (3)	0.002 (3)
C12	0.031 (5)	0.016 (5)	0.027 (5)	0.006 (4)	0.005 (4)	0.009 (4)
C13	0.011 (4)	0.016 (4)	0.020 (4)	0.005 (4)	0.005 (3)	−0.006 (3)
C14	0.023 (5)	0.020 (5)	0.023 (5)	0.005 (4)	0.002 (4)	0.004 (4)
C15	0.031 (5)	0.022 (5)	0.020 (5)	0.005 (4)	0.006 (4)	0.011 (4)
C16	0.015 (4)	0.021 (5)	0.020 (4)	0.000 (4)	0.002 (3)	0.007 (4)
C17	0.015 (4)	0.018 (4)	0.024 (4)	0.012 (3)	0.001 (3)	0.004 (3)
C18	0.012 (4)	0.018 (4)	0.014 (4)	0.001 (3)	0.001 (3)	0.002 (3)
C19	0.014 (4)	0.032 (5)	0.021 (4)	0.011 (4)	0.009 (3)	0.011 (4)
C20	0.033 (5)	0.013 (4)	0.022 (5)	0.004 (4)	0.008 (4)	0.007 (3)
C21	0.026 (5)	0.011 (5)	0.027 (5)	0.004 (4)	−0.001 (4)	0.008 (4)

Geometric parameters (Å, º) top

Ce1—O1ⁱ	2.349 (6)	O15—H15A	0.8200
Ce1—O3	2.773 (5)	N1—C5	1.319 (10)
Ce1—O4	2.570 (5)	N1—C1	1.342 (9)
Ce1—O5ⁱⁱ	2.384 (5)	N2—C8	1.343 (10)
Ce1—O7	2.538 (5)	N2—C12	1.332 (10)
Ce1—O9	2.538 (5)	N3—C15	1.333 (10)
Ce1—O11ⁱⁱⁱ	2.405 (5)	N3—C19	1.346 (9)
Ce1—O13	2.560 (5)	C1—C2	1.389 (11)
Ce2—O2^iv	2.404 (5)	C2—C6	1.505 (10)
Ce2—O3	2.594 (5)	C2—C3	1.372 (10)
Ce2—O6^v	2.431 (5)	C3—C4	1.391 (10)
Ce2—O7	2.847 (6)	C4—C5	1.392 (11)
Ce2—O8	2.657 (6)	C4—C7	1.494 (11)
Ce2—O10^vi	2.526 (5)	C8—C9	1.375 (11)
Ce2—O12ⁱⁱⁱ	2.444 (5)	C9—C13	1.532 (10)
Ce2—O14	2.606 (6)	C9—C10	1.375 (10)
Ce2—O15	2.646 (6)	C10—C11	1.376 (10)
O1—C6	1.253 (10)	C11—C12	1.383 (11)
O2—C6	1.240 (10)	C11—C14	1.511 (11)
O3—C7	1.275 (9)	C15—C16	1.376 (11)
O4—C7	1.264 (10)	C16—C17	1.377 (10)
O5—C13	1.259 (9)	C16—C20	1.519 (11)
O6—C13	1.247 (9)	C17—C18	1.388 (10)
O7—C14	1.293 (10)	C18—C21	1.497 (10)
O8—C14	1.236 (10)	C18—C19	1.376 (11)
O9—C20	1.255 (9)	C1—H1	0.9300
O10—C20	1.250 (10)	C3—H3	0.9300
O11—C21	1.268 (9)	C5—H5	0.9300
O12—C21	1.238 (10)	C8—H8	0.9300
O13—H13B	0.8100	C10—H10	0.9300
O13—H13A	0.8200	C12—H12	0.9300
O14—H14A	0.8900	C15—H15	0.9300
O14—H14B	0.8800	C17—H17	0.9300
O15—H15B	0.8200	C19—H19	0.9300

O3—Ce1—O4	48.97 (15)	Ce1ⁱⁱⁱ—O11—C21	139.0 (5)
O3—Ce1—O7	63.21 (15)	Ce2ⁱⁱⁱ—O12—C21	147.9 (5)
O3—Ce1—O9	136.42 (15)	Ce1—O13—H13B	109.00
O3—Ce1—O13	74.86 (16)	H13A—O13—H13B	110.00
O3—Ce1—O5ⁱⁱ	142.09 (15)	Ce1—O13—H13A	109.00
O1ⁱ—Ce1—O3	116.29 (16)	H14A—O14—H14B	105.00
O3—Ce1—O11ⁱⁱⁱ	81.13 (16)	Ce2—O14—H14A	146.00
O4—Ce1—O7	78.59 (15)	Ce2—O14—H14B	89.00
O4—Ce1—O9	138.31 (16)	Ce2—O15—H15A	103.00
O4—Ce1—O13	84.43 (15)	H15A—O15—H15B	109.00
O4—Ce1—O5ⁱⁱ	130.62 (15)	Ce2—O15—H15B	119.00
O1ⁱ—Ce1—O4	71.74 (17)	C1—N1—C5	117.6 (7)
O4—Ce1—O11ⁱⁱⁱ	130.01 (18)	C8—N2—C12	116.8 (7)
O7—Ce1—O9	76.13 (17)	C15—N3—C19	115.7 (7)
O7—Ce1—O13	135.85 (17)	N1—C1—C2	122.7 (7)
O5ⁱⁱ—Ce1—O7	148.48 (15)	C1—C2—C3	118.5 (6)
O1ⁱ—Ce1—O7	86.99 (17)	C1—C2—C6	119.9 (7)
O7—Ce1—O11ⁱⁱⁱ	81.55 (16)	C3—C2—C6	121.6 (7)
O9—Ce1—O13	135.94 (17)	C2—C3—C4	119.9 (7)
O5ⁱⁱ—Ce1—O9	73.22 (16)	C3—C4—C5	116.8 (7)
O1ⁱ—Ce1—O9	74.33 (17)	C5—C4—C7	120.8 (7)
O9—Ce1—O11ⁱⁱⁱ	77.93 (17)	C3—C4—C7	122.3 (7)
O5ⁱⁱ—Ce1—O13	67.88 (17)	N1—C5—C4	124.4 (7)
O1ⁱ—Ce1—O13	125.59 (16)	O1—C6—C2	116.4 (7)
O11ⁱⁱⁱ—Ce1—O13	78.89 (16)	O1—C6—O2	125.6 (7)
O1ⁱ—Ce1—O5ⁱⁱ	91.67 (18)	O2—C6—C2	118.0 (7)
O5ⁱⁱ—Ce1—O11ⁱⁱⁱ	85.06 (17)	O3—C7—C4	118.9 (7)
O1ⁱ—Ce1—O11ⁱⁱⁱ	151.80 (16)	O3—C7—O4	122.2 (7)
O3—Ce2—O7	61.49 (13)	O4—C7—C4	118.9 (6)
O3—Ce2—O8	76.02 (16)	N2—C8—C9	123.3 (7)
O3—Ce2—O14	142.80 (16)	C8—C9—C10	118.4 (7)
O3—Ce2—O15	132.35 (17)	C8—C9—C13	118.8 (7)
O3—Ce2—O10^vi	142.82 (16)	C10—C9—C13	122.9 (6)
O3—Ce2—O6^v	71.96 (15)	C9—C10—C11	119.9 (7)
O3—Ce2—O12ⁱⁱⁱ	81.25 (15)	C10—C11—C12	117.5 (7)
O2^iv—Ce2—O3	86.49 (15)	C12—C11—C14	119.6 (7)
O7—Ce2—O8	47.39 (15)	C10—C11—C14	122.9 (7)
O7—Ce2—O14	103.05 (15)	N2—C12—C11	124.1 (7)
O7—Ce2—O15	73.85 (16)	O5—C13—C9	116.3 (6)
O7—Ce2—O10^vi	137.07 (15)	O6—C13—C9	117.7 (6)
O6^v—Ce2—O7	126.71 (16)	O5—C13—O6	126.1 (7)
O7—Ce2—O12ⁱⁱⁱ	73.06 (16)	O8—C14—C11	120.8 (7)
O2^iv—Ce2—O7	115.52 (16)	O7—C14—O8	122.7 (8)
O8—Ce2—O14	69.99 (17)	O7—C14—C11	116.6 (7)
O8—Ce2—O15	86.20 (19)	N3—C15—C16	124.9 (7)
O8—Ce2—O10^vi	141.16 (17)	C15—C16—C20	118.4 (7)
O6^v—Ce2—O8	141.34 (16)	C17—C16—C20	123.8 (7)
O8—Ce2—O12ⁱⁱⁱ	120.16 (17)	C15—C16—C17	117.8 (7)
O2^iv—Ce2—O8	72.51 (18)	C16—C17—C18	119.5 (7)
O14—Ce2—O15	60.51 (19)	C17—C18—C19	117.7 (6)
O10^vi—Ce2—O14	72.40 (17)	C17—C18—C21	122.5 (7)
O6^v—Ce2—O14	130.08 (18)	C19—C18—C21	119.6 (6)
O12ⁱⁱⁱ—Ce2—O14	129.11 (16)	N3—C19—C18	124.4 (7)
O2^iv—Ce2—O14	69.45 (17)	O9—C20—C16	116.5 (7)
O10^vi—Ce2—O15	66.93 (18)	O10—C20—C16	117.2 (6)
O6^v—Ce2—O15	131.76 (17)	O9—C20—O10	126.4 (7)
O12ⁱⁱⁱ—Ce2—O15	70.20 (17)	O12—C21—C18	117.4 (7)
O2^iv—Ce2—O15	129.76 (18)	O11—C21—O12	125.5 (7)
O6^v—Ce2—O10^vi	73.31 (16)	O11—C21—C18	117.1 (7)
O10^vi—Ce2—O12ⁱⁱⁱ	77.76 (17)	N1—C1—H1	119.00
O2^iv—Ce2—O10^vi	102.93 (17)	C2—C1—H1	119.00
O6^v—Ce2—O12ⁱⁱⁱ	75.75 (16)	C2—C3—H3	120.00
O2^iv—Ce2—O6^v	84.34 (17)	C4—C3—H3	120.00
O2^iv—Ce2—O12ⁱⁱⁱ	159.05 (16)	N1—C5—H5	118.00
Ce1ⁱ—O1—C6	151.9 (5)	C4—C5—H5	118.00
Ce2^iv—O2—C6	159.8 (5)	N2—C8—H8	118.00
Ce1—O3—Ce2	111.94 (16)	C9—C8—H8	118.00
Ce1—O3—C7	89.4 (4)	C9—C10—H10	120.00
Ce2—O3—C7	126.0 (4)	C11—C10—H10	120.00
Ce1—O4—C7	99.2 (4)	N2—C12—H12	118.00
Ce1^vii—O5—C13	133.9 (4)	C11—C12—H12	118.00
Ce2^viii—O6—C13	147.4 (5)	N3—C15—H15	118.00
Ce1—O7—Ce2	111.32 (17)	C16—C15—H15	118.00
Ce1—O7—C14	127.9 (4)	C16—C17—H17	120.00
Ce2—O7—C14	89.2 (5)	C18—C17—H17	120.00
Ce2—O8—C14	99.6 (5)	N3—C19—H19	118.00
Ce1—O9—C20	155.6 (5)	C18—C19—H19	118.00
Ce2^ix—O10—C20	118.3 (4)

O4—Ce1—O3—Ce2	127.0 (2)	O14—Ce2—O10^vi—C20^vi	−71.9 (5)
O4—Ce1—O3—C7	−2.0 (4)	O15—Ce2—O10^vi—C20^vi	−136.7 (6)
O7—Ce1—O3—Ce2	28.62 (16)	O3—Ce2—O6^v—C13^v	160.2 (9)
O7—Ce1—O3—C7	−100.4 (4)	O7—Ce2—O6^v—C13^v	−170.1 (8)
O9—Ce1—O3—Ce2	5.6 (3)	O8—Ce2—O6^v—C13^v	124.7 (8)
O9—Ce1—O3—C7	−123.5 (4)	O14—Ce2—O6^v—C13^v	15.1 (9)
O13—Ce1—O3—Ce2	−137.1 (2)	O15—Ce2—O6^v—C13^v	−68.5 (9)
O13—Ce1—O3—C7	93.8 (4)	O3—Ce2—O12ⁱⁱⁱ—C21ⁱⁱⁱ	−29.8 (9)
O5ⁱⁱ—Ce1—O3—Ce2	−126.3 (2)	O7—Ce2—O12ⁱⁱⁱ—C21ⁱⁱⁱ	33.0 (9)
O5ⁱⁱ—Ce1—O3—C7	104.7 (4)	O8—Ce2—O12ⁱⁱⁱ—C21ⁱⁱⁱ	38.4 (9)
O1ⁱ—Ce1—O3—Ce2	100.26 (19)	O14—Ce2—O12ⁱⁱⁱ—C21ⁱⁱⁱ	126.2 (8)
O1ⁱ—Ce1—O3—C7	−28.8 (4)	O15—Ce2—O12ⁱⁱⁱ—C21ⁱⁱⁱ	111.5 (9)
O11ⁱⁱⁱ—Ce1—O3—Ce2	−56.34 (18)	O3—Ce2—O2^iv—C6^iv	−123.2 (14)
O11ⁱⁱⁱ—Ce1—O3—C7	174.6 (4)	O7—Ce2—O2^iv—C6^iv	−179.2 (13)
O3—Ce1—O4—C7	2.1 (4)	O8—Ce2—O2^iv—C6^iv	160.3 (14)
O7—Ce1—O4—C7	66.4 (4)	O14—Ce2—O2^iv—C6^iv	85.7 (14)
O9—Ce1—O4—C7	119.9 (4)	O15—Ce2—O2^iv—C6^iv	91.0 (14)
O13—Ce1—O4—C7	−72.7 (4)	Ce1ⁱ—O1—C6—O2	12.2 (16)
O5ⁱⁱ—Ce1—O4—C7	−127.1 (4)	Ce1ⁱ—O1—C6—C2	−170.3 (7)
O1ⁱ—Ce1—O4—C7	157.0 (4)	Ce2^iv—O2—C6—O1	−20.9 (19)
O11ⁱⁱⁱ—Ce1—O4—C7	−2.2 (5)	Ce2^iv—O2—C6—C2	161.7 (10)
O3—Ce1—O7—Ce2	−25.76 (14)	Ce1—O3—C7—O4	3.7 (7)
O3—Ce1—O7—C14	80.9 (6)	Ce1—O3—C7—C4	−175.9 (6)
O4—Ce1—O7—Ce2	−75.35 (18)	Ce2—O3—C7—O4	−113.4 (7)
O4—Ce1—O7—C14	31.3 (6)	Ce2—O3—C7—C4	67.0 (8)
O9—Ce1—O7—Ce2	138.1 (2)	Ce1—O4—C7—O3	−4.0 (7)
O9—Ce1—O7—C14	−115.3 (6)	Ce1—O4—C7—C4	175.6 (6)
O13—Ce1—O7—Ce2	−5.8 (3)	Ce1^vii—O5—C13—O6	74.3 (9)
O13—Ce1—O7—C14	100.8 (6)	Ce1^vii—O5—C13—C9	−108.1 (6)
O5ⁱⁱ—Ce1—O7—Ce2	124.4 (3)	Ce2^viii—O6—C13—O5	−78.9 (11)
O5ⁱⁱ—Ce1—O7—C14	−129.0 (6)	Ce2^viii—O6—C13—C9	103.6 (9)
O1ⁱ—Ce1—O7—Ce2	−147.32 (18)	Ce1—O7—C14—O8	−106.4 (8)
O1ⁱ—Ce1—O7—C14	−40.7 (6)	Ce1—O7—C14—C11	73.6 (8)
O11ⁱⁱⁱ—Ce1—O7—Ce2	58.52 (18)	Ce2—O7—C14—O8	10.4 (7)
O11ⁱⁱⁱ—Ce1—O7—C14	165.2 (6)	Ce2—O7—C14—C11	−169.6 (6)
O3—Ce1—O9—C20	−81.5 (12)	Ce2—O8—C14—O7	−11.3 (8)
O4—Ce1—O9—C20	−156.9 (11)	Ce2—O8—C14—C11	168.7 (6)
O7—Ce1—O9—C20	−102.6 (12)	Ce1—O9—C20—O10	−119.1 (11)
O13—Ce1—O9—C20	41.3 (13)	Ce1—O9—C20—C16	60.1 (14)
O5ⁱⁱ—Ce1—O9—C20	70.0 (12)	Ce2^ix—O10—C20—O9	−16.0 (10)
O1ⁱ—Ce1—O9—C20	166.6 (12)	Ce2^ix—O10—C20—C16	164.8 (5)
O11ⁱⁱⁱ—Ce1—O9—C20	−18.5 (12)	Ce1ⁱⁱⁱ—O11—C21—O12	23.5 (12)
O3—Ce1—O5ⁱⁱ—C13ⁱⁱ	146.4 (6)	Ce1ⁱⁱⁱ—O11—C21—C18	−154.5 (5)
O4—Ce1—O5ⁱⁱ—C13ⁱⁱ	−141.4 (6)	Ce2ⁱⁱⁱ—O12—C21—O11	−9.9 (14)
O7—Ce1—O5ⁱⁱ—C13ⁱⁱ	12.8 (8)	Ce2ⁱⁱⁱ—O12—C21—C18	168.1 (5)
O9—Ce1—O5ⁱⁱ—C13ⁱⁱ	−1.1 (6)	C5—N1—C1—C2	0.2 (10)
O13—Ce1—O5ⁱⁱ—C13ⁱⁱ	157.7 (6)	C1—N1—C5—C4	2.4 (11)
O3—Ce1—O1ⁱ—C6ⁱ	−159.3 (10)	C12—N2—C8—C9	1.3 (11)
O4—Ce1—O1ⁱ—C6ⁱ	179.7 (10)	C8—N2—C12—C11	1.0 (11)
O7—Ce1—O1ⁱ—C6ⁱ	−101.3 (10)	C19—N3—C15—C16	0.7 (11)
O9—Ce1—O1ⁱ—C6ⁱ	−24.9 (10)	C15—N3—C19—C18	−1.0 (11)
O13—Ce1—O1ⁱ—C6ⁱ	110.9 (10)	N1—C1—C2—C3	−2.2 (10)
O3—Ce1—O11ⁱⁱⁱ—C21ⁱⁱⁱ	46.7 (7)	N1—C1—C2—C6	175.0 (6)
O4—Ce1—O11ⁱⁱⁱ—C21ⁱⁱⁱ	50.0 (8)	C1—C2—C3—C4	1.7 (9)
O7—Ce1—O11ⁱⁱⁱ—C21ⁱⁱⁱ	−17.4 (7)	C6—C2—C3—C4	−175.4 (6)
O9—Ce1—O11ⁱⁱⁱ—C21ⁱⁱⁱ	−94.9 (7)	C1—C2—C6—O1	178.4 (6)
O13—Ce1—O11ⁱⁱⁱ—C21ⁱⁱⁱ	122.9 (7)	C1—C2—C6—O2	−3.9 (10)
O7—Ce2—O3—Ce1	−25.70 (14)	C3—C2—C6—O1	−4.6 (10)
O7—Ce2—O3—C7	80.5 (6)	C3—C2—C6—O2	173.2 (6)
O8—Ce2—O3—Ce1	−74.50 (19)	C2—C3—C4—C5	0.7 (10)
O8—Ce2—O3—C7	31.7 (6)	C2—C3—C4—C7	179.1 (6)
O14—Ce2—O3—Ce1	−98.8 (3)	C3—C4—C5—N1	−2.8 (11)
O14—Ce2—O3—C7	7.4 (7)	C7—C4—C5—N1	178.7 (7)
O15—Ce2—O3—Ce1	−3.1 (3)	C3—C4—C7—O3	−153.3 (7)
O15—Ce2—O3—C7	103.1 (6)	C3—C4—C7—O4	27.1 (10)
O10^vi—Ce2—O3—Ce1	105.8 (3)	C5—C4—C7—O3	25.1 (10)
O10^vi—Ce2—O3—C7	−148.0 (5)	C5—C4—C7—O4	−154.5 (7)
O6^v—Ce2—O3—Ce1	127.5 (2)	N2—C8—C9—C10	−2.7 (11)
O6^v—Ce2—O3—C7	−126.3 (6)	N2—C8—C9—C13	175.7 (6)
O12ⁱⁱⁱ—Ce2—O3—Ce1	49.71 (18)	C8—C9—C10—C11	1.8 (10)
O12ⁱⁱⁱ—Ce2—O3—C7	155.9 (6)	C13—C9—C10—C11	−176.5 (7)
O2^iv—Ce2—O3—Ce1	−147.3 (2)	C8—C9—C13—O5	−180.0 (6)
O2^iv—Ce2—O3—C7	−41.1 (6)	C8—C9—C13—O6	−2.2 (10)
O3—Ce2—O7—Ce1	28.16 (15)	C10—C9—C13—O5	−1.7 (10)
O3—Ce2—O7—C14	−102.8 (4)	C10—C9—C13—O6	176.1 (7)
O8—Ce2—O7—Ce1	125.4 (3)	C9—C10—C11—C12	0.4 (11)
O8—Ce2—O7—C14	−5.5 (4)	C9—C10—C11—C14	−179.0 (7)
O14—Ce2—O7—Ce1	171.72 (18)	C10—C11—C12—N2	−1.8 (11)
O14—Ce2—O7—C14	40.8 (4)	C14—C11—C12—N2	177.6 (7)
O15—Ce2—O7—Ce1	−134.7 (2)	C10—C11—C14—O7	−159.1 (7)
O15—Ce2—O7—C14	94.4 (4)	C10—C11—C14—O8	20.9 (11)
O10^vi—Ce2—O7—Ce1	−110.2 (2)	C12—C11—C14—O7	21.5 (10)
O10^vi—Ce2—O7—C14	118.9 (4)	C12—C11—C14—O8	−158.5 (7)
O6^v—Ce2—O7—Ce1	−4.2 (2)	N3—C15—C16—C17	0.6 (12)
O6^v—Ce2—O7—C14	−135.1 (4)	N3—C15—C16—C20	−178.8 (7)
O12ⁱⁱⁱ—Ce2—O7—Ce1	−60.96 (17)	C15—C16—C17—C18	−1.6 (11)
O12ⁱⁱⁱ—Ce2—O7—C14	168.1 (4)	C20—C16—C17—C18	177.7 (7)
O2^iv—Ce2—O7—Ce1	98.5 (2)	C15—C16—C20—O9	26.0 (10)
O2^iv—Ce2—O7—C14	−32.4 (4)	C15—C16—C20—O10	−154.8 (7)
O3—Ce2—O8—C14	69.8 (5)	C17—C16—C20—O9	−153.4 (7)
O7—Ce2—O8—C14	5.9 (4)	C17—C16—C20—O10	25.9 (11)
O14—Ce2—O8—C14	−125.6 (5)	C16—C17—C18—C19	1.4 (11)
O15—Ce2—O8—C14	−65.6 (5)	C16—C17—C18—C21	−173.6 (7)
O10^vi—Ce2—O8—C14	−110.5 (5)	C17—C18—C19—N3	0.0 (11)
O6^v—Ce2—O8—C14	104.5 (5)	C21—C18—C19—N3	175.1 (7)
O12ⁱⁱⁱ—Ce2—O8—C14	−1.2 (5)	C17—C18—C21—O11	−178.9 (7)
O2^iv—Ce2—O8—C14	160.5 (5)	C17—C18—C21—O12	2.9 (11)
O3—Ce2—O10^vi—C20^vi	92.8 (6)	C19—C18—C21—O11	6.2 (10)
O7—Ce2—O10^vi—C20^vi	−162.3 (5)	C19—C18—C21—O12	−172.0 (7)
O8—Ce2—O10^vi—C20^vi	−86.8 (6)

Symmetry codes: (i) −x, −y, −z+1; (ii) x, y+1, z; (iii) −x, −y+1, −z; (iv) −x+1, −y, −z+1; (v) x+1, y+1, z; (vi) x+1, y, z; (vii) x, y−1, z; (viii) x−1, y−1, z; (ix) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13A···O4^x	0.82	2.28	2.901 (7)	132
O13—H13B···N1^xi	0.81	1.87	2.659 (9)	164
O14—H14A···N2^vi	0.89	2.06	2.802 (9)	140
O14—H14B···O10^vi	0.88	2.40	3.031 (9)	129
O15—H15A···O10^vi	0.82	2.40	2.853 (9)	115
O15—H15B···N3	0.82	2.00	2.815 (9)	174
C8—H8···O12^xii	0.93	2.43	3.354 (9)	172
C12—H12···O9	0.93	2.57	3.354 (9)	143
C15—H15···O7	0.93	2.38	3.258 (9)	157

Symmetry codes: (vi) x+1, y, z; (x) −x, −y+1, −z+1; (xi) −x+1, −y+1, −z+1; (xii) −x−1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Ce₂(C₇H₃NO₄)₃(H₂O)₃]
M_r	829.60
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.959 (3), 9.429 (3), 14.582 (4)
α, β, γ (°)	98.115 (6), 95.501 (6), 105.030 (6)
V (Å³)	1166.4 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.94
Crystal size (mm)	0.15 × 0.08 × 0.02

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.756, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	12583, 5586, 2847
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.076, 0.74
No. of reflections	5586
No. of parameters	370
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	1.36, −1.15

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top

Ce1—O1ⁱ	2.349 (6)	Ce2—O3	2.594 (5)
Ce1—O3	2.773 (5)	Ce2—O6^v	2.431 (5)
Ce1—O4	2.570 (5)	Ce2—O7	2.847 (6)
Ce1—O5ⁱⁱ	2.384 (5)	Ce2—O8	2.657 (6)
Ce1—O7	2.538 (5)	Ce2—O10^vi	2.526 (5)
Ce1—O9	2.538 (5)	Ce2—O12ⁱⁱⁱ	2.444 (5)
Ce1—O11ⁱⁱⁱ	2.405 (5)	Ce2—O14	2.606 (6)
Ce1—O13	2.560 (5)	Ce2—O15	2.646 (6)
Ce2—O2^iv	2.404 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13A···O4^vii	0.82	2.28	2.901 (7)	132
O13—H13B···N1^viii	0.81	1.87	2.659 (9)	164
O14—H14A···N2^vi	0.89	2.06	2.802 (9)	140
O14—H14B···O10^vi	0.88	2.40	3.031 (9)	129
O15—H15A···O10^vi	0.82	2.40	2.853 (9)	115
O15—H15B···N3	0.82	2.00	2.815 (9)	174
C8—H8···O12^ix	0.93	2.43	3.354 (9)	172
C12—H12···O9	0.93	2.57	3.354 (9)	143
C15—H15···O7	0.93	2.38	3.258 (9)	157

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

Acknowledgements

This work was supported financially by Yuanpei University, Taiwan.

References

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