Poly[[diaqua­[μ2-3-carb­oxy-5-(pyridine-4-carboxamido)­benzoato][μ4-5-(pyridine-4-carboxamido)­isophthalato]cerium(III)] monohydrate]

Deng, Y.-F.; Nie, X.

doi:10.1107/S1600536812013402

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m530

doi:10.1107/S1600536812013402

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Poly[[diaqua[μ₂-3-carboxy-5-(pyridine-4-carboxamido)benzoato][μ₄-5-(pyridine-4-carboxamido)isophthalato]cerium(III)] monohydrate]

Yi-Fang Deng ^a ^* and Xue Nie ^a

^aDepartment of Chemistry and Materials Science, Hengyang Normal University, Hengyang 421008, People's Republic of China
^*Correspondence e-mail: yifang7124@163.com

(Received 16 March 2012; accepted 28 March 2012; online 4 April 2012)

In the title compound, {[Ce(C₁₄H₉N₂O₅)(C₁₄H₈N₂O₅)(H₂O)₂]·H₂O}_n, three carboxyl groups of two independent isophthalate anions are deprotonated and they bridge the Ce^III cations, forming a two-dimensional polymeric structure parallel to (001); another carboxyl group is not deprotonated and links with the adjacent pyridine ring via an O—H⋯N hydrogen bond. The Ce^III cation is coordinated by six O atoms from carboxyl groups and two O atoms from coordinated water molecules in a distorted square-antiprismatic arrangement. Extensive O—H⋯O and O—H⋯N hydrogen bonding occurs in the crystal structure.

Related literature

For applications of lanthanide complexes with carboxyl ligands, see: Chin et al. (1994 ); Singh et al. (2002 ). For related complexes, see: Chen et al. (2011 ); Deng (2011 ); Qiu et al. (2007 ); Gubina et al. (2000 ); Wang et al. (2003 ).

Experimental

Crystal data

[Ce(C₁₄H₉N₂O₅)(C₁₄H₈N₂O₅)(H₂O)₂]·H₂O
M_r = 763.62
Triclinic, $[P \overline 1]$
a = 9.6742 (8) Å
b = 10.6187 (8) Å
c = 15.8542 (12) Å
α = 81.443 (1)°
β = 78.753 (2)°
γ = 64.166 (2)°
V = 1433.98 (19) Å³
Z = 2
Mo Kα radiation
μ = 1.67 mm⁻¹
T = 293 K
0.18 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.754, T_max = 0.878
7189 measured reflections
4972 independent reflections
4669 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.086
S = 1.04
4972 reflections
416 parameters
H-atom parameters constrained
Δρ_max = 1.26 e Å⁻³
Δρ_min = −1.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯N2ⁱ	0.85	2.21	2.756 (5)	122
O2W—H2WB⋯O1Wⁱⁱ	0.85	2.53	3.297 (5)	150
O2W—H2WA⋯O3Wⁱⁱⁱ	0.85	2.07	2.728 (6)	133
O3W—H3WA⋯O10^iv	0.85	2.06	2.856 (8)	157
O3W—H3WB⋯O5^v	0.85	1.92	2.742 (6)	161
O3—H3⋯N4^vi	0.82	1.81	2.583 (5)	156
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+2, -y+2, -z+1; (iii) x, y+1, z; (iv) x-1, y, z; (v) -x+1, -y+1, -z+1; (vi) -x+3, -y+2, -z+1.

Data collection: APEX2 (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: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812013402/xu5485sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013402/xu5485Isup2.hkl

checkCIF report

Comment top

Recently, lanthanide-carboxylic acid complexes have been widely studied and applied in many fields due to their excellent luminescent properties (Chin et al., 1994; Singh et al., 2002). Distinct structure features with various lanthanides (Qiu et al., 2007; Gubina et al., 2000) or ligands (Wang et al., 2003) have been reported.

The title compound, (I) was synthesized and its structure was determined by X-ray diffraction. Similar crystal structure with 5-isonicotinamidoisophthalic acid as ligand has been reported recently (Chen et al., 2011; Deng, 2011).

In the title compound, the central Ce^III ion is eight-coordinated by two O atoms from two water molecules, two carboxylate O atoms from two partial-deprotonated HL^- ligands and four other O atoms from four different L^2- ligands, which forming a distorted square-antiprismatic geometry (Fig. 1). Moreover, the HL^- anions adopt µ₂-η¹:η¹ bridging coordination mode, while two carboxylate groups of each L^2- ligand have different coordination modes, one is µ₂-η¹:η¹ bridging and the other one acts as µ₂-η²:η¹-bridging coordination mode, whereas the pyridyl group is free of coordination. Such a coordination mode makes (I) into an infinite two-dimensional network (Fig. 2). The pyridyl groups are free. Adjacent molecules are linked through O—H···N and O—H···O hydrogen bonds into a three-dimensional network.

Related literature top

For applications of lanthanide complexes with carboxyl ligands, see: Chin et al. (1994); Singh et al. (2002). For related complexes, see: Chen et al. (2011); Deng (2011); Qiu et al. (2007); Gubina et al. (2000); Wang et al. (2003).

Experimental top

A mixture of 0.05 mmol Ce(NO₃)₃.6H₂O (21.2 mg. 0.05 mmol), 5-isonicotinamidoisophthalic acid (28.7 mg, 0.1 mmol), NaOH (6.0 mg, 0.15 mmol), MeOH (5 ml) and water (5 ml) was heated in a 16 ml capacity Teflon-lined reaction vessel at 453 K for 3 d, the reaction mixture then was cooled to room temperature over a period of 40 h. The product was collected by filtration.

Computing details top

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The ORTEP drawing of the title compound (I). Displacement ellipsoids are drawn at 30% probability level. [Symmetry codes: (i) 1 - x,2 - y,1 - z (ii) 2 - x,2 - y,1 - z (iii) -1 + x,1 + y,z (iv) 2 - x,1 - y,1 - z.]
	Fig. 2. Projection showing the two-dimensional structure of the compound, all pyridyl groups are omitted for clarity.

Poly[[diaqua[µ₂-3-carboxy-5-(pyridine-4-carboxamido)benzoato][µ₄- 5-(pyridine-4-carboxamido)isophthalato]cerium(III)] monohydrate] top

Crystal data top

[Ce(C₁₄H₉N₂O₅)(C₁₄H₈N₂O₅)(H₂O)₂]·H₂O	Z = 2
M_r = 763.62	F(000) = 762
Triclinic, P1	D_x = 1.769 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6742 (8) Å	Cell parameters from 4972 reflections
b = 10.6187 (8) Å	θ = 2.1–25.0°
c = 15.8542 (12) Å	µ = 1.67 mm⁻¹
α = 81.443 (1)°	T = 293 K
β = 78.753 (2)°	Block, colorless
γ = 64.166 (2)°	0.18 × 0.14 × 0.08 mm
V = 1433.98 (19) Å³

Data collection top

Bruker APEXII CCD diffractometer	4972 independent reflections
Radiation source: fine-focus sealed tube	4669 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.754, T_max = 0.878	k = −10→12
7189 measured reflections	l = −16→18

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0565P)²] where P = (F_o² + 2F_c²)/3
4972 reflections	(Δ/σ)_max = 0.002
416 parameters	Δρ_max = 1.26 e Å⁻³
0 restraints	Δρ_min = −1.23 e Å⁻³

Crystal data top

[Ce(C₁₄H₉N₂O₅)(C₁₄H₈N₂O₅)(H₂O)₂]·H₂O	γ = 64.166 (2)°
M_r = 763.62	V = 1433.98 (19) Å³
Triclinic, P1	Z = 2
a = 9.6742 (8) Å	Mo Kα radiation
b = 10.6187 (8) Å	µ = 1.67 mm⁻¹
c = 15.8542 (12) Å	T = 293 K
α = 81.443 (1)°	0.18 × 0.14 × 0.08 mm
β = 78.753 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4972 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4669 reflections with I > 2σ(I)
T_min = 0.754, T_max = 0.878	R_int = 0.071
7189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.04	Δρ_max = 1.26 e Å⁻³
4972 reflections	Δρ_min = −1.23 e Å⁻³
416 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	0.731679 (19)	0.960889 (17)	0.503370 (11)	0.01875 (9)
C7	0.5111 (4)	1.0993 (4)	0.3253 (2)	0.0249 (7)
C3	0.5318 (4)	1.1620 (4)	0.2339 (2)	0.0259 (7)
C2	0.4389 (4)	1.1697 (4)	0.1751 (2)	0.0288 (8)
H2	0.3671	1.1309	0.1903	0.035*
C1	0.4534 (4)	1.2359 (4)	0.0934 (2)	0.0299 (8)
C6	0.5503 (5)	1.3043 (4)	0.0741 (2)	0.0353 (9)
H6	0.5531	1.3560	0.0215	0.042*
C5	0.6427 (5)	1.2962 (4)	0.1326 (2)	0.0323 (8)
C4	0.6388 (4)	1.2197 (4)	0.2109 (2)	0.0299 (8)
H4	0.7079	1.2070	0.2481	0.036*
C9	0.3250 (5)	1.1435 (5)	0.0155 (3)	0.0385 (9)
C10	0.2671 (5)	1.1588 (4)	−0.0677 (2)	0.0364 (9)
C14	0.1640 (6)	1.1015 (5)	−0.0707 (3)	0.0480 (11)
H14	0.1281	1.0590	−0.0213	0.058*
C13	0.1153 (6)	1.1087 (6)	−0.1486 (3)	0.0575 (13)
H13	0.0458	1.0705	−0.1502	0.069*
C12	0.2624 (7)	1.2209 (6)	−0.2179 (3)	0.0562 (13)
H12	0.2969	1.2615	−0.2687	0.067*
C11	0.3175 (6)	1.2199 (5)	−0.1436 (3)	0.0496 (11)
H11	0.3869	1.2593	−0.1445	0.059*
C8	0.7431 (5)	1.3750 (5)	0.1128 (3)	0.0398 (10)
C21	1.1064 (4)	0.7882 (3)	0.5569 (2)	0.0212 (7)
C17	1.2354 (4)	0.6476 (3)	0.5727 (2)	0.0210 (7)
C16	1.3614 (4)	0.6391 (4)	0.6063 (2)	0.0254 (7)
H16	1.3649	0.7207	0.6183	0.031*
C15	1.4816 (4)	0.5108 (4)	0.6220 (2)	0.0267 (7)
C20	1.4817 (4)	0.3891 (4)	0.6011 (2)	0.0267 (8)
H20	1.5633	0.3028	0.6113	0.032*
C19	1.3580 (4)	0.3973 (4)	0.5645 (2)	0.0230 (7)
C18	1.2335 (4)	0.5254 (3)	0.5521 (2)	0.0223 (7)
H18	1.1491	0.5296	0.5301	0.027*
C23	1.6591 (5)	0.4429 (4)	0.7281 (3)	0.0389 (9)
C24	1.7777 (4)	0.4767 (4)	0.7573 (3)	0.0337 (9)
C28	1.8537 (5)	0.5516 (5)	0.7061 (3)	0.0429 (10)
H28	1.8401	0.5784	0.6487	0.052*
C27	1.9499 (5)	0.5854 (5)	0.7425 (3)	0.0487 (12)
H27	1.9997	0.6369	0.7083	0.058*
C26	1.9051 (5)	0.4746 (5)	0.8713 (3)	0.0410 (10)
H26	1.9236	0.4468	0.9280	0.049*
C25	1.8059 (5)	0.4367 (5)	0.8415 (3)	0.0388 (10)
H25	1.7583	0.3848	0.8773	0.047*
C22	1.3639 (4)	0.2695 (4)	0.5316 (2)	0.0266 (7)
N1	0.3669 (4)	1.2433 (4)	0.0286 (2)	0.0359 (8)
H2A	0.4223	1.2574	−0.0215	0.043*
N2	0.1632 (5)	1.1672 (5)	−0.2205 (3)	0.0572 (11)
N3	1.6082 (4)	0.5117 (3)	0.6555 (2)	0.0326 (7)
H3A	1.6550	0.5606	0.6263	0.039*
N4	1.9759 (4)	0.5488 (4)	0.8236 (2)	0.0443 (9)
O1	0.3837 (3)	1.0938 (3)	0.35242 (16)	0.0368 (6)
O2	0.6201 (3)	1.0635 (3)	0.36808 (16)	0.0342 (6)
O3	0.8519 (5)	1.3290 (5)	0.1605 (3)	0.0757 (13)
H3	0.8914	1.3846	0.1553	0.114*
O4	0.7212 (4)	1.4718 (4)	0.0589 (2)	0.0537 (9)
O5	0.3353 (5)	1.0419 (4)	0.0661 (2)	0.0589 (10)
O6	0.9822 (3)	0.7910 (2)	0.54280 (17)	0.0303 (6)
O7	1.1291 (3)	0.8947 (2)	0.56132 (17)	0.0300 (6)
O8	1.4778 (3)	0.1545 (3)	0.53961 (18)	0.0381 (6)
O9	1.2553 (4)	0.2827 (3)	0.4946 (3)	0.0585 (10)
O10	1.6089 (5)	0.3622 (5)	0.7707 (2)	0.0748 (13)
O1W	0.9238 (4)	0.8370 (3)	0.37514 (18)	0.0537 (8)
H1WB	0.8907	0.7774	0.3687	0.064*
H1WA	0.9094	0.8880	0.3282	0.064*
O2W	0.7983 (3)	1.0672 (3)	0.61536 (17)	0.0369 (6)
H2WB	0.8768	1.0855	0.5974	0.044*
H2WA	0.8080	1.0189	0.6634	0.044*
O3W	0.7921 (9)	0.0666 (7)	0.7882 (3)	0.141 (3)
H3WA	0.7410	0.1497	0.7680	0.169*
H3WB	0.7469	0.0249	0.8251	0.169*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ce1	0.01952 (13)	0.01527 (12)	0.02393 (13)	−0.00835 (9)	−0.00774 (8)	0.00066 (8)
C7	0.0299 (19)	0.0230 (18)	0.0252 (17)	−0.0131 (15)	−0.0082 (14)	0.0005 (14)
C3	0.0283 (19)	0.0244 (18)	0.0276 (18)	−0.0127 (15)	−0.0074 (14)	0.0006 (14)
C2	0.032 (2)	0.032 (2)	0.0277 (18)	−0.0182 (17)	−0.0085 (15)	0.0009 (15)
C1	0.036 (2)	0.032 (2)	0.0289 (18)	−0.0183 (17)	−0.0137 (16)	0.0009 (15)
C6	0.044 (2)	0.040 (2)	0.0303 (19)	−0.026 (2)	−0.0115 (17)	0.0070 (17)
C5	0.038 (2)	0.037 (2)	0.0312 (19)	−0.0241 (18)	−0.0091 (16)	0.0024 (16)
C4	0.034 (2)	0.032 (2)	0.0304 (19)	−0.0181 (17)	−0.0119 (16)	0.0007 (15)
C9	0.047 (2)	0.044 (2)	0.036 (2)	−0.028 (2)	−0.0153 (18)	0.0044 (19)
C10	0.046 (2)	0.038 (2)	0.032 (2)	−0.0217 (19)	−0.0141 (17)	0.0011 (17)
C14	0.058 (3)	0.059 (3)	0.042 (2)	−0.035 (3)	−0.018 (2)	0.000 (2)
C13	0.062 (3)	0.064 (3)	0.058 (3)	−0.027 (3)	−0.026 (3)	−0.016 (3)
C12	0.070 (3)	0.068 (3)	0.032 (2)	−0.027 (3)	−0.016 (2)	−0.001 (2)
C11	0.062 (3)	0.056 (3)	0.040 (2)	−0.034 (3)	−0.012 (2)	0.001 (2)
C8	0.051 (3)	0.051 (3)	0.035 (2)	−0.037 (2)	−0.0121 (19)	0.0044 (19)
C21	0.0236 (17)	0.0231 (17)	0.0196 (16)	−0.0112 (14)	−0.0054 (13)	−0.0020 (13)
C17	0.0207 (17)	0.0190 (17)	0.0262 (17)	−0.0101 (14)	−0.0072 (13)	0.0006 (13)
C16	0.0284 (19)	0.0244 (18)	0.0305 (18)	−0.0159 (15)	−0.0086 (14)	−0.0013 (14)
C15	0.0250 (18)	0.0271 (19)	0.0315 (18)	−0.0121 (15)	−0.0116 (15)	0.0016 (15)
C20	0.0250 (18)	0.0212 (18)	0.0341 (19)	−0.0086 (15)	−0.0094 (15)	0.0008 (14)
C19	0.0227 (17)	0.0216 (17)	0.0273 (17)	−0.0114 (14)	−0.0059 (14)	0.0006 (14)
C18	0.0204 (17)	0.0209 (17)	0.0302 (18)	−0.0115 (14)	−0.0069 (14)	−0.0018 (14)
C23	0.040 (2)	0.040 (2)	0.046 (2)	−0.023 (2)	−0.0188 (19)	0.0057 (19)
C24	0.029 (2)	0.034 (2)	0.042 (2)	−0.0148 (17)	−0.0149 (17)	0.0018 (17)
C28	0.043 (2)	0.060 (3)	0.037 (2)	−0.030 (2)	−0.0140 (18)	0.006 (2)
C27	0.046 (3)	0.071 (3)	0.046 (2)	−0.041 (3)	−0.015 (2)	0.008 (2)
C26	0.039 (2)	0.053 (3)	0.036 (2)	−0.023 (2)	−0.0123 (18)	0.0020 (19)
C25	0.038 (2)	0.045 (2)	0.041 (2)	−0.024 (2)	−0.0171 (18)	0.0103 (19)
C22	0.0270 (19)	0.0203 (18)	0.0343 (19)	−0.0124 (15)	−0.0035 (15)	−0.0009 (14)
N1	0.049 (2)	0.045 (2)	0.0279 (16)	−0.0308 (17)	−0.0168 (15)	0.0070 (14)
N2	0.068 (3)	0.060 (3)	0.042 (2)	−0.014 (2)	−0.026 (2)	−0.0129 (19)
N3	0.0294 (17)	0.0320 (17)	0.0443 (18)	−0.0168 (14)	−0.0195 (14)	0.0048 (14)
N4	0.043 (2)	0.064 (2)	0.0414 (19)	−0.035 (2)	−0.0151 (16)	0.0026 (17)
O1	0.0304 (15)	0.0464 (17)	0.0334 (14)	−0.0189 (13)	−0.0077 (11)	0.0105 (12)
O2	0.0380 (15)	0.0454 (16)	0.0303 (13)	−0.0250 (13)	−0.0175 (12)	0.0055 (12)
O3	0.088 (3)	0.102 (3)	0.083 (3)	−0.080 (3)	−0.057 (2)	0.047 (2)
O4	0.074 (2)	0.061 (2)	0.0481 (18)	−0.0527 (19)	−0.0203 (16)	0.0207 (16)
O5	0.099 (3)	0.059 (2)	0.0472 (18)	−0.057 (2)	−0.0355 (19)	0.0185 (16)
O6	0.0256 (13)	0.0224 (13)	0.0483 (15)	−0.0106 (11)	−0.0172 (12)	−0.0009 (11)
O7	0.0316 (14)	0.0194 (12)	0.0454 (15)	−0.0148 (11)	−0.0152 (12)	0.0045 (11)
O8	0.0426 (17)	0.0220 (14)	0.0433 (16)	−0.0051 (12)	−0.0116 (13)	−0.0035 (11)
O9	0.051 (2)	0.0288 (16)	0.111 (3)	−0.0155 (14)	−0.041 (2)	−0.0168 (17)
O10	0.089 (3)	0.099 (3)	0.076 (2)	−0.076 (3)	−0.051 (2)	0.042 (2)
O1W	0.069 (2)	0.0480 (19)	0.0349 (16)	−0.0105 (17)	−0.0130 (15)	−0.0133 (14)
O2W	0.0388 (16)	0.0416 (16)	0.0379 (15)	−0.0226 (13)	−0.0083 (12)	−0.0033 (12)
O3W	0.230 (8)	0.154 (6)	0.076 (3)	−0.129 (6)	−0.007 (4)	0.011 (4)

Geometric parameters (Å, º) top

Ce1—O1ⁱ	2.446 (2)	C17—C16	1.385 (5)
Ce1—O2	2.477 (2)	C17—C18	1.393 (5)
Ce1—O6	2.442 (2)	C16—C15	1.379 (5)
Ce1—O7ⁱⁱ	2.452 (2)	C16—H16	0.9300
Ce1—O8ⁱⁱⁱ	2.447 (3)	C15—C20	1.381 (5)
Ce1—O9^iv	2.530 (3)	C15—N3	1.431 (4)
Ce1—O1W	2.552 (3)	C20—C19	1.394 (5)
Ce1—O2W	2.553 (3)	C20—H20	0.9300
C7—O1	1.248 (4)	C19—C18	1.387 (5)
C7—O2	1.252 (4)	C19—C22	1.498 (5)
C7—C3	1.517 (5)	C18—H18	0.9300
C3—C4	1.385 (5)	C23—O10	1.220 (5)
C3—C2	1.386 (5)	C23—N3	1.326 (5)
C2—C1	1.392 (5)	C23—C24	1.508 (5)
C2—H2	0.9300	C24—C25	1.382 (5)
C1—C6	1.385 (5)	C24—C28	1.384 (6)
C1—N1	1.419 (4)	C28—C27	1.374 (6)
C6—C5	1.377 (5)	C28—H28	0.9300
C6—H6	0.9300	C27—N4	1.326 (6)
C5—C4	1.383 (5)	C27—H27	0.9300
C5—C8	1.501 (5)	C26—N4	1.324 (6)
C4—H4	0.9300	C26—C25	1.369 (6)
C9—O5	1.224 (5)	C26—H26	0.9300
C9—N1	1.344 (5)	C25—H25	0.9300
C9—C10	1.492 (5)	C22—O9	1.247 (4)
C10—C11	1.386 (6)	C22—O8	1.248 (4)
C10—C14	1.387 (6)	N1—H2A	0.8998
C14—C13	1.386 (6)	N3—H3A	0.8600
C14—H14	0.9300	O1—Ce1ⁱ	2.446 (2)
C13—N2	1.316 (7)	O3—H3	0.8200
C13—H13	0.9300	O7—Ce1ⁱⁱ	2.452 (2)
C12—N2	1.322 (7)	O8—Ce1^v	2.447 (3)
C12—C11	1.381 (6)	O9—Ce1^iv	2.530 (3)
C12—H12	0.9300	O1W—H1WB	0.8499
C11—H11	0.9300	O1W—H1WA	0.8495
C8—O4	1.205 (5)	O2W—H2WB	0.8506
C8—O3	1.291 (5)	O2W—H2WA	0.8495
C21—O6	1.252 (4)	O3W—H3WA	0.8496
C21—O7	1.256 (4)	O3W—H3WB	0.8500
C21—C17	1.496 (5)

O6—Ce1—O1ⁱ	87.00 (9)	O4—C8—O3	124.6 (4)
O6—Ce1—O8ⁱⁱⁱ	150.29 (9)	O4—C8—C5	122.7 (4)
O1ⁱ—Ce1—O8ⁱⁱⁱ	71.37 (9)	O3—C8—C5	112.8 (4)
O6—Ce1—O7ⁱⁱ	85.08 (8)	O6—C21—O7	124.9 (3)
O1ⁱ—Ce1—O7ⁱⁱ	137.06 (9)	O6—C21—C17	117.5 (3)
O8ⁱⁱⁱ—Ce1—O7ⁱⁱ	96.89 (9)	O7—C21—C17	117.6 (3)
O6—Ce1—O2	136.56 (9)	C16—C17—C18	119.4 (3)
O1ⁱ—Ce1—O2	131.89 (9)	C16—C17—C21	119.3 (3)
O8ⁱⁱⁱ—Ce1—O2	72.04 (9)	C18—C17—C21	121.3 (3)
O7ⁱⁱ—Ce1—O2	77.34 (8)	C15—C16—C17	120.6 (3)
O6—Ce1—O9^iv	71.67 (9)	C15—C16—H16	119.7
O1ⁱ—Ce1—O9^iv	72.84 (12)	C17—C16—H16	119.7
O8ⁱⁱⁱ—Ce1—O9^iv	118.35 (10)	C16—C15—C20	120.5 (3)
O7ⁱⁱ—Ce1—O9^iv	141.86 (11)	C16—C15—N3	117.0 (3)
O2—Ce1—O9^iv	98.94 (10)	C20—C15—N3	122.4 (3)
O6—Ce1—O1W	66.88 (9)	C15—C20—C19	119.2 (3)
O1ⁱ—Ce1—O1W	140.12 (10)	C15—C20—H20	120.4
O8ⁱⁱⁱ—Ce1—O1W	141.96 (9)	C19—C20—H20	120.4
O7ⁱⁱ—Ce1—O1W	72.58 (10)	C18—C19—C20	120.4 (3)
O2—Ce1—O1W	70.00 (10)	C18—C19—C22	119.1 (3)
O9^iv—Ce1—O1W	70.61 (12)	C20—C19—C22	120.3 (3)
O6—Ce1—O2W	72.59 (9)	C19—C18—C17	119.8 (3)
O1ⁱ—Ce1—O2W	70.31 (9)	C19—C18—H18	120.1
O8ⁱⁱⁱ—Ce1—O2W	80.89 (9)	C17—C18—H18	120.1
O7ⁱⁱ—Ce1—O2W	67.04 (9)	O10—C23—N3	122.6 (4)
O2—Ce1—O2W	131.79 (9)	O10—C23—C24	121.9 (4)
O9^iv—Ce1—O2W	129.14 (10)	N3—C23—C24	115.5 (3)
O1W—Ce1—O2W	124.10 (10)	C25—C24—C28	118.2 (4)
O1—C7—O2	125.7 (3)	C25—C24—C23	117.8 (4)
O1—C7—C3	116.8 (3)	C28—C24—C23	123.9 (3)
O2—C7—C3	117.4 (3)	C27—C28—C24	118.2 (4)
C4—C3—C2	119.9 (3)	C27—C28—H28	120.9
C4—C3—C7	119.1 (3)	C24—C28—H28	120.9
C2—C3—C7	120.8 (3)	N4—C27—C28	123.8 (4)
C3—C2—C1	119.7 (3)	N4—C27—H27	118.1
C3—C2—H2	120.1	C28—C27—H27	118.1
C1—C2—H2	120.1	N4—C26—C25	123.4 (4)
C6—C1—C2	119.6 (3)	N4—C26—H26	118.3
C6—C1—N1	117.3 (3)	C25—C26—H26	118.3
C2—C1—N1	123.1 (3)	C26—C25—C24	119.0 (4)
C5—C6—C1	120.2 (4)	C26—C25—H25	120.5
C5—C6—H6	119.9	C24—C25—H25	120.5
C1—C6—H6	119.9	O9—C22—O8	121.8 (3)
C6—C5—C4	120.1 (3)	O9—C22—C19	118.4 (3)
C6—C5—C8	120.1 (3)	O8—C22—C19	119.8 (3)
C4—C5—C8	119.8 (3)	C9—N1—C1	125.9 (3)
C5—C4—C3	119.9 (3)	C9—N1—H2A	105.5
C5—C4—H4	120.0	C1—N1—H2A	105.1
C3—C4—H4	120.0	C13—N2—C12	118.3 (4)
O5—C9—N1	124.0 (4)	C23—N3—C15	125.0 (3)
O5—C9—C10	119.6 (4)	C23—N3—H3A	117.5
N1—C9—C10	116.4 (3)	C15—N3—H3A	117.5
C11—C10—C14	118.0 (4)	C26—N4—C27	117.4 (4)
C11—C10—C9	123.6 (4)	C7—O1—Ce1ⁱ	131.8 (2)
C14—C10—C9	118.3 (4)	C7—O2—Ce1	149.8 (2)
C13—C14—C10	118.9 (5)	C8—O3—H3	109.5
C13—C14—H14	120.5	C21—O6—Ce1	139.3 (2)
C10—C14—H14	120.5	C21—O7—Ce1ⁱⁱ	147.2 (2)
N2—C13—C14	122.8 (5)	C22—O8—Ce1^v	159.1 (3)
N2—C13—H13	118.6	C22—O9—Ce1^iv	106.3 (2)
C14—C13—H13	118.6	Ce1—O1W—H1WB	101.1
N2—C12—C11	123.5 (5)	Ce1—O1W—H1WA	112.4
N2—C12—H12	118.3	H1WB—O1W—H1WA	101.8
C11—C12—H12	118.3	Ce1—O2W—H2WB	113.4
C12—C11—C10	118.5 (5)	Ce1—O2W—H2WA	113.3
C12—C11—H11	120.8	H2WB—O2W—H2WA	110.7
C10—C11—H11	120.8	H3WA—O3W—H3WB	120.4

O1—C7—C3—C4	155.7 (4)	N3—C23—C24—C28	−12.3 (6)
O2—C7—C3—C4	−21.2 (5)	C25—C24—C28—C27	−1.7 (7)
O1—C7—C3—C2	−20.4 (5)	C23—C24—C28—C27	174.8 (4)
O2—C7—C3—C2	162.7 (3)	C24—C28—C27—N4	0.9 (8)
C4—C3—C2—C1	−0.2 (6)	N4—C26—C25—C24	0.3 (7)
C7—C3—C2—C1	175.9 (3)	C28—C24—C25—C26	1.2 (6)
C3—C2—C1—C6	−5.8 (6)	C23—C24—C25—C26	−175.5 (4)
C3—C2—C1—N1	177.5 (4)	C18—C19—C22—O9	−0.5 (5)
C2—C1—C6—C5	6.0 (6)	C20—C19—C22—O9	−175.7 (4)
N1—C1—C6—C5	−177.1 (4)	C18—C19—C22—O8	177.5 (3)
C1—C6—C5—C4	−0.1 (6)	C20—C19—C22—O8	2.3 (5)
C1—C6—C5—C8	−177.7 (4)	O5—C9—N1—C1	11.9 (7)
C6—C5—C4—C3	−5.9 (6)	C10—C9—N1—C1	−166.3 (4)
C8—C5—C4—C3	171.6 (4)	C6—C1—N1—C9	148.1 (4)
C2—C3—C4—C5	6.0 (6)	C2—C1—N1—C9	−35.2 (6)
C7—C3—C4—C5	−170.1 (3)	C14—C13—N2—C12	0.2 (8)
O5—C9—C10—C11	−147.1 (5)	C11—C12—N2—C13	−0.5 (8)
N1—C9—C10—C11	31.2 (7)	O10—C23—N3—C15	5.8 (7)
O5—C9—C10—C14	29.0 (7)	C24—C23—N3—C15	−171.2 (3)
N1—C9—C10—C14	−152.7 (4)	C16—C15—N3—C23	123.6 (4)
C11—C10—C14—C13	−0.4 (7)	C20—C15—N3—C23	−60.1 (5)
C9—C10—C14—C13	−176.8 (5)	C25—C26—N4—C27	−1.1 (7)
C10—C14—C13—N2	0.3 (8)	C28—C27—N4—C26	0.5 (8)
N2—C12—C11—C10	0.3 (8)	O2—C7—O1—Ce1ⁱ	7.2 (6)
C14—C10—C11—C12	0.2 (7)	C3—C7—O1—Ce1ⁱ	−169.5 (2)
C9—C10—C11—C12	176.3 (5)	O1—C7—O2—Ce1	4.2 (8)
C6—C5—C8—O4	18.6 (7)	C3—C7—O2—Ce1	−179.1 (3)
C4—C5—C8—O4	−158.9 (4)	O6—Ce1—O2—C7	134.9 (5)
C6—C5—C8—O3	−162.3 (4)	O1ⁱ—Ce1—O2—C7	−12.8 (5)
C4—C5—C8—O3	20.1 (6)	O8ⁱⁱⁱ—Ce1—O2—C7	−54.9 (5)
O6—C21—C17—C16	−166.5 (3)	O7ⁱⁱ—Ce1—O2—C7	−156.5 (5)
O7—C21—C17—C16	11.6 (5)	O9^iv—Ce1—O2—C7	62.2 (5)
O6—C21—C17—C18	15.4 (5)	O1W—Ce1—O2—C7	127.6 (5)
O7—C21—C17—C18	−166.6 (3)	O2W—Ce1—O2—C7	−114.0 (5)
C18—C17—C16—C15	−2.2 (5)	O7—C21—O6—Ce1	7.3 (6)
C21—C17—C16—C15	179.6 (3)	C17—C21—O6—Ce1	−174.9 (2)
C17—C16—C15—C20	2.8 (5)	O1ⁱ—Ce1—O6—C21	−112.6 (4)
C17—C16—C15—N3	179.1 (3)	O8ⁱⁱⁱ—Ce1—O6—C21	−70.1 (4)
C16—C15—C20—C19	−0.5 (5)	O7ⁱⁱ—Ce1—O6—C21	25.2 (3)
N3—C15—C20—C19	−176.6 (3)	O2—Ce1—O6—C21	90.9 (4)
C15—C20—C19—C18	−2.4 (5)	O9^iv—Ce1—O6—C21	174.5 (4)
C15—C20—C19—C22	172.8 (3)	O1W—Ce1—O6—C21	98.3 (4)
C20—C19—C18—C17	3.0 (5)	O2W—Ce1—O6—C21	−42.3 (3)
C22—C19—C18—C17	−172.2 (3)	O6—C21—O7—Ce1ⁱⁱ	−112.8 (4)
C16—C17—C18—C19	−0.7 (5)	C17—C21—O7—Ce1ⁱⁱ	69.4 (5)
C21—C17—C18—C19	177.5 (3)	O9—C22—O8—Ce1^v	85.9 (8)
O10—C23—C24—C25	−12.8 (7)	C19—C22—O8—Ce1^v	−92.0 (8)
N3—C23—C24—C25	164.2 (4)	O8—C22—O9—Ce1^iv	20.5 (5)
O10—C23—C24—C28	170.6 (5)	C19—C22—O9—Ce1^iv	−161.5 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N2^vi	0.85	2.21	2.756 (5)	122
O2W—H2WB···O1Wⁱⁱ	0.85	2.53	3.297 (5)	150
O2W—H2WA···O3W^vii	0.85	2.07	2.728 (6)	133
O3W—H3WA···O10^viii	0.85	2.06	2.856 (8)	157
O3W—H3WB···O5^ix	0.85	1.92	2.742 (6)	161
O3—H3···N4^x	0.82	1.81	2.583 (5)	156

Symmetry codes: (ii) −x+2, −y+2, −z+1; (vi) −x+1, −y+2, −z; (vii) x, y+1, z; (viii) x−1, y, z; (ix) −x+1, −y+1, −z+1; (x) −x+3, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ce(C₁₄H₉N₂O₅)(C₁₄H₈N₂O₅)(H₂O)₂]·H₂O
M_r	763.62
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.6742 (8), 10.6187 (8), 15.8542 (12)
α, β, γ (°)	81.443 (1), 78.753 (2), 64.166 (2)
V (Å³)	1433.98 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.67
Crystal size (mm)	0.18 × 0.14 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.754, 0.878
No. of measured, independent and observed [I > 2σ(I)] reflections	7189, 4972, 4669
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.086, 1.04
No. of reflections	4972
No. of parameters	416
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.26, −1.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N2ⁱ	0.85	2.21	2.756 (5)	122.1
O2W—H2WB···O1Wⁱⁱ	0.85	2.53	3.297 (5)	150.4
O2W—H2WA···O3Wⁱⁱⁱ	0.85	2.07	2.728 (6)	133.3
O3W—H3WA···O10^iv	0.85	2.06	2.856 (8)	156.8
O3W—H3WB···O5^v	0.85	1.92	2.742 (6)	161.0
O3—H3···N4^vi	0.82	1.81	2.583 (5)	155.6

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

Acknowledgements

This work was supported by the Hengyang Bureau of Science & Technology, China (grant No. 2009 K J28).

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