Poly[aqua­[μ5-5-(isonicotinamido)­isophthalato][μ4-5-(isonicotinamido)­isophthalato]cerium(III)silver(I)]

Nie, X.; Qu, J.-N.

doi:10.1107/S1600536811027668

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages m1107-m1108

doi:10.1107/S1600536811027668

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Poly[aqua[μ₅-5-(isonicotinamido)isophthalato][μ₄-5-(isonicotinamido)isophthalato]cerium(III)silver(I)]

Xue Nie ^a ^* and Jing-Nian Qu ^a

^aDepartment of Chemistry and Materials Science, Hengyang, Hunan 421008, People's Republic of China
^*Correspondence e-mail: xuehuanie@126.com

(Received 22 June 2011; accepted 11 July 2011; online 23 July 2011)

The 4d–4f heteronuclear title complex, [AgCe(C₁₄H₈N₂O₅)₂(H₂O)]_n, has a three-dimensional framework structure, generated by the carboxylate and pyridyl groups of the 5-(isonicotinamido)isophthalate (INAIP) ligands bridging the metal ions. The Ce^III atom is coordinated by eight O atoms from six INAIP ligands and a water molecule in a distorted tricapped trigonal–prismatic geometry, while the Ag^I atom has a distorted trigonal–planar AgN₂O geometry. O—H⋯O and N—H⋯O hydrogen bonds and π–π interactions between the pyridine and benzene rings [centroid–centroid distances = 3.642 (4) and 3.624 (3) Å] stabilize the crystal structure.

Related literature

For background to coordination polymers, see: Abourahma et al. (2002 ); Costes et al. (2004 ); Kapoor et al. (2002 ). For background to lanthanide and transition metal heterometallic compounds, see: Chen et al. (2010 ); Cheng et al. (2006 ); Lin et al. (2009 ); Zhang et al. (2005 ).

Experimental

Crystal data

[AgCe(C₁₄H₈N₂O₅)₂(H₂O)]
M_r = 834.45
Triclinic, $[P \overline 1]$
a = 10.4869 (14) Å
b = 11.1540 (15) Å
c = 13.7276 (18) Å
α = 107.853 (1)°
β = 106.778 (2)°
γ = 102.885 (2)°
V = 1375.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.42 mm⁻¹
T = 293 K
0.20 × 0.14 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.643, T_max = 0.794
6903 measured reflections
4777 independent reflections
4178 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.081
S = 0.97
4777 reflections
406 parameters
H-atom parameters constrained
Δρ_max = 1.40 e Å⁻³
Δρ_min = −1.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O5ⁱ	0.85	2.08	2.836 (5)	147
O1W—H1WB⋯O4ⁱⁱ	0.85	2.01	2.691 (6)	137
N2—H2⋯O10ⁱⁱⁱ	0.86	2.01	2.788 (7)	149
N4—H4⋯O4ⁱ	0.86	2.08	2.926 (6)	167
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z; (iii) x, y+1, z.

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: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027668/hy2446sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027668/hy2446Isup2.hkl

checkCIF report

Comment top

In recent years, coordination polymeric frameworks have attracted great attention because of their potential applications and intriguing structure topologies (Abourahma et al., 2002; Costes et al., 2004; Kapoor et al., 2002). To obtain d-f coordination polymers is more important. In general, multidentate ligands containing both N- and O-donor atoms are usually employed in the construction of lanthanide (Ln) and transition metal (M) heterometallic structures, in keeping with the typical coordination behaviors of Ln and M ions under different reaction conditions (Cheng et al., 2006; Lin et al., 2009; Zhang et al., 2005). Compared with other N-heterocyclic acids, 5-(isonicotinamido)isophthalic acid (H₂INAIP) shows richer coordination modes due to its two carboxylate groups and one pyridyl group, and accordingly it is an excellent candidate for the construction of metal-organic frameworks (Chen et al., 2010). In this paper, we report the synthesis and structure of the title complex (Fig. 1), a 4d-4f heterometallic coordination polymer.

It is interesting that two INAIP ligands exhibit different coordination modes: one coordinated to three Ce^III atoms and two Ag^I atoms while the other coordinated to three Ce^III atoms and one Ag^I atom, originated from the different coordination modes of the carboxylate groups. If the Ag—N and Ag—O connections are neglected, a two-dimensional (4, 4) bilayer network is formed by the Ce^III–carboxylate coordination. The (4, 4) nets are linked together by Ag—N and Ag—O coordination interactions, forming a complicated three-dimensional coordination net (Fig. 2).

Related literature top

For background to coordination polymers, see: Abourahma et al. (2002); Costes et al. (2004); Kapoor et al. (2002). For background to lanthanide and transition metal heterometallic compounds, see: Chen et al. (2010); Cheng et al. (2006); Lin et al. (2009); Zhang et al. (2005).

Experimental top

A mixture of Ce(NO₃)₃.6H₂O (22.0 mg, 0.05 mmol), H₂INAIP (28.6 mg, 0.1 mmol), AgNO₃ (8.5 mg, 0.05 mmol), NaOH (6.0 mg, 0.15 mmol) and H₂O (10 ml) was heated in a 16 ml Teflon-lined reaction vessel at 453 K for 4 d. The reaction mixture was cooled to room temperature over a period of 40 h. The product was collected by filtration, washed with H₂O and air dried.

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

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (A) 1-x, 1-y, 1-z; (B) 1+x, y, z; (C) 1-x, -y, 1-z; (D) x, 1+y, z; (E) x, y, 1+z; (F) 2-x, 1-y, 3-z.]
	Fig. 2. A view of the three-dimensional framework of the title compound.

Poly[aqua[µ₅-5-(isonicotinamido)isophthalato][µ₄-5- (isonicotinamido)isophthalato]cerium(III)silver(I)] top

Crystal data top

[AgCe(C₁₄H₈N₂O₅)₂(H₂O)]	Z = 2
M_r = 834.45	F(000) = 814
Triclinic, P1	D_x = 2.015 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4869 (14) Å	Cell parameters from 4777 reflections
b = 11.1540 (15) Å	θ = 2.0–25.0°
c = 13.7276 (18) Å	µ = 2.42 mm⁻¹
α = 107.853 (1)°	T = 293 K
β = 106.778 (2)°	Block, colorless
γ = 102.885 (2)°	0.20 × 0.14 × 0.10 mm
V = 1375.2 (3) Å³

Data collection top

Bruker APEX CCD diffractometer	4777 independent reflections
Radiation source: fine-focus sealed tube	4178 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.643, T_max = 0.794	k = −11→13
6903 measured reflections	l = −16→12

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0347P)²] where P = (F_o² + 2F_c²)/3
4777 reflections	(Δ/σ)_max = 0.001
406 parameters	Δρ_max = 1.40 e Å⁻³
0 restraints	Δρ_min = −1.44 e Å⁻³

Crystal data top

[AgCe(C₁₄H₈N₂O₅)₂(H₂O)]	γ = 102.885 (2)°
M_r = 834.45	V = 1375.2 (3) Å³
Triclinic, P1	Z = 2
a = 10.4869 (14) Å	Mo Kα radiation
b = 11.1540 (15) Å	µ = 2.42 mm⁻¹
c = 13.7276 (18) Å	T = 293 K
α = 107.853 (1)°	0.20 × 0.14 × 0.10 mm
β = 106.778 (2)°

Data collection top

Bruker APEX CCD diffractometer	4777 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4178 reflections with I > 2σ(I)
T_min = 0.643, T_max = 0.794	R_int = 0.053
6903 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 0.97	Δρ_max = 1.40 e Å⁻³
4777 reflections	Δρ_min = −1.44 e Å⁻³
406 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ag1	0.88225 (5)	0.23184 (7)	1.55049 (4)	0.06266 (18)
Ce1	0.63603 (3)	0.45288 (2)	0.61285 (2)	0.01607 (9)
C1	0.3260 (5)	0.5683 (4)	0.5961 (4)	0.0200 (10)
C2	0.2981 (5)	0.5843 (4)	0.7000 (4)	0.0202 (10)
C3	0.1600 (5)	0.5553 (4)	0.6961 (4)	0.0222 (10)
H3	0.0837	0.5240	0.6288	0.027*
C4	0.1376 (5)	0.5735 (5)	0.7933 (4)	0.0234 (10)
C5	0.2530 (5)	0.6195 (5)	0.8932 (4)	0.0247 (11)
H5	0.2378	0.6312	0.9584	0.030*
C6	0.3879 (5)	0.6476 (4)	0.8964 (4)	0.0209 (10)
C7	0.4116 (5)	0.6312 (4)	0.8000 (4)	0.0223 (10)
H7	0.5037	0.6517	0.8023	0.027*
C8	−0.0077 (5)	0.5580 (5)	0.7942 (4)	0.0240 (11)
C9	0.5223 (5)	0.6542 (5)	1.0769 (4)	0.0236 (11)
C10	0.6688 (5)	0.7096 (5)	1.1656 (4)	0.0260 (11)
C11	0.6840 (6)	0.7319 (6)	1.2735 (4)	0.0398 (14)
H11	0.6052	0.7199	1.2925	0.048*
C12	0.8176 (6)	0.7723 (7)	1.3521 (4)	0.0469 (16)
H12	0.8272	0.7904	1.4252	0.056*
C13	0.9185 (6)	0.7691 (7)	1.2276 (5)	0.0481 (16)
H13	0.9993	0.7828	1.2112	0.058*
C14	0.7895 (6)	0.7313 (6)	1.1433 (4)	0.0418 (14)
H14	0.7840	0.7205	1.0721	0.050*
C15	0.6561 (5)	0.2158 (5)	0.6570 (4)	0.0240 (11)
C16	0.6919 (5)	0.1164 (4)	0.7036 (4)	0.0217 (10)
C17	0.7361 (5)	0.1512 (5)	0.8175 (4)	0.0258 (11)
H17	0.7431	0.2353	0.8638	0.031*
C18	0.7693 (5)	0.0620 (5)	0.8619 (4)	0.0252 (11)
C19	0.7550 (5)	−0.0648 (5)	0.7921 (4)	0.0241 (11)
H19	0.7773	−0.1255	0.8219	0.029*
C20	0.7076 (5)	−0.1014 (4)	0.6784 (4)	0.0215 (10)
C21	0.6768 (5)	−0.0101 (4)	0.6344 (4)	0.0223 (10)
H21	0.6460	−0.0340	0.5582	0.027*
C22	0.6810 (5)	−0.2419 (5)	0.6031 (4)	0.0212 (10)
C23	0.7450 (6)	0.0246 (5)	1.0210 (4)	0.0356 (13)
C24	0.7834 (6)	0.0781 (5)	1.1428 (4)	0.0318 (12)
C25	0.6756 (6)	0.0579 (6)	1.1812 (5)	0.0428 (14)
H25	0.5819	0.0151	1.1312	0.051*
C26	0.7064 (7)	0.1008 (6)	1.2925 (5)	0.0437 (14)
H26	0.6321	0.0865	1.3165	0.052*
C27	0.9447 (6)	0.1839 (6)	1.3330 (5)	0.0452 (15)
H27	1.0375	0.2270	1.3846	0.054*
C28	0.9196 (6)	0.1435 (6)	1.2209 (4)	0.0384 (14)
H28	0.9950	0.1608	1.1985	0.046*
N1	0.9338 (5)	0.7871 (5)	1.3303 (4)	0.0409 (12)
N2	0.5085 (4)	0.6990 (4)	0.9965 (3)	0.0249 (9)
H2	0.5787	0.7647	1.0061	0.030*
N3	0.8395 (5)	0.1627 (5)	1.3687 (4)	0.0401 (12)
N4	0.8112 (5)	0.0994 (4)	0.9783 (3)	0.0285 (10)
H4	0.8810	0.1721	1.0226	0.034*
O1	0.4458 (3)	0.5621 (3)	0.5960 (2)	0.0233 (7)
O2	0.2324 (4)	0.5616 (4)	0.5135 (3)	0.0329 (9)
O3	−0.1121 (3)	0.4777 (3)	0.7074 (3)	0.0280 (8)
O4	−0.0163 (4)	0.6309 (4)	0.8809 (3)	0.0341 (9)
O5	0.4260 (4)	0.5710 (3)	1.0791 (3)	0.0316 (8)
O6	0.6166 (4)	0.3009 (3)	0.7118 (3)	0.0280 (8)
O7	0.6661 (4)	0.2109 (3)	0.5664 (2)	0.0241 (7)
O8	0.6024 (4)	−0.2802 (3)	0.5023 (3)	0.0270 (8)
O9	0.7369 (3)	−0.3125 (3)	0.6448 (3)	0.0259 (8)
O10	0.6548 (5)	−0.0862 (4)	0.9625 (3)	0.0639 (14)
O1W	0.7032 (3)	0.5815 (3)	0.8217 (3)	0.0266 (8)
H1WB	0.7778	0.5704	0.8568	0.032*
H1WA	0.6372	0.5446	0.8383	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0349 (3)	0.1311 (5)	0.0321 (3)	0.0401 (3)	0.0142 (2)	0.0360 (3)
Ce1	0.01710 (15)	0.01732 (14)	0.01439 (14)	0.00767 (11)	0.00504 (11)	0.00675 (10)
C1	0.022 (3)	0.018 (2)	0.019 (2)	0.006 (2)	0.008 (2)	0.005 (2)
C2	0.020 (3)	0.025 (2)	0.020 (2)	0.012 (2)	0.009 (2)	0.011 (2)
C3	0.020 (3)	0.025 (2)	0.017 (2)	0.008 (2)	0.003 (2)	0.007 (2)
C4	0.022 (3)	0.027 (3)	0.021 (3)	0.009 (2)	0.008 (2)	0.009 (2)
C5	0.026 (3)	0.033 (3)	0.015 (2)	0.015 (2)	0.006 (2)	0.009 (2)
C6	0.021 (3)	0.021 (2)	0.018 (2)	0.007 (2)	0.004 (2)	0.008 (2)
C7	0.019 (3)	0.027 (3)	0.024 (3)	0.010 (2)	0.009 (2)	0.012 (2)
C8	0.022 (3)	0.030 (3)	0.020 (3)	0.009 (2)	0.006 (2)	0.013 (2)
C9	0.024 (3)	0.026 (3)	0.015 (2)	0.006 (2)	0.005 (2)	0.005 (2)
C10	0.028 (3)	0.027 (3)	0.025 (3)	0.011 (2)	0.008 (2)	0.013 (2)
C11	0.026 (3)	0.072 (4)	0.025 (3)	0.019 (3)	0.011 (2)	0.021 (3)
C12	0.035 (4)	0.081 (5)	0.023 (3)	0.024 (3)	0.006 (3)	0.020 (3)
C13	0.025 (3)	0.082 (5)	0.040 (4)	0.017 (3)	0.011 (3)	0.030 (3)
C14	0.032 (3)	0.070 (4)	0.022 (3)	0.011 (3)	0.011 (3)	0.021 (3)
C15	0.021 (3)	0.024 (3)	0.029 (3)	0.010 (2)	0.008 (2)	0.015 (2)
C16	0.022 (3)	0.019 (2)	0.026 (3)	0.008 (2)	0.008 (2)	0.012 (2)
C17	0.034 (3)	0.020 (2)	0.024 (3)	0.010 (2)	0.012 (2)	0.008 (2)
C18	0.029 (3)	0.024 (3)	0.019 (2)	0.006 (2)	0.009 (2)	0.008 (2)
C19	0.027 (3)	0.023 (2)	0.024 (3)	0.011 (2)	0.005 (2)	0.013 (2)
C20	0.023 (3)	0.018 (2)	0.024 (3)	0.007 (2)	0.008 (2)	0.010 (2)
C21	0.023 (3)	0.023 (2)	0.020 (2)	0.008 (2)	0.006 (2)	0.010 (2)
C22	0.017 (3)	0.026 (2)	0.022 (3)	0.006 (2)	0.009 (2)	0.011 (2)
C23	0.041 (3)	0.029 (3)	0.030 (3)	0.007 (3)	0.009 (3)	0.011 (3)
C24	0.040 (3)	0.030 (3)	0.028 (3)	0.011 (3)	0.013 (3)	0.015 (2)
C25	0.034 (3)	0.048 (3)	0.032 (3)	0.006 (3)	0.005 (3)	0.011 (3)
C26	0.041 (4)	0.063 (4)	0.035 (3)	0.020 (3)	0.020 (3)	0.024 (3)
C27	0.035 (4)	0.076 (4)	0.033 (3)	0.026 (3)	0.013 (3)	0.028 (3)
C28	0.041 (4)	0.058 (4)	0.028 (3)	0.023 (3)	0.018 (3)	0.024 (3)
N1	0.026 (3)	0.064 (3)	0.028 (3)	0.016 (2)	0.004 (2)	0.018 (2)
N2	0.019 (2)	0.030 (2)	0.020 (2)	0.0024 (18)	0.0017 (18)	0.0124 (18)
N3	0.043 (3)	0.061 (3)	0.030 (3)	0.029 (3)	0.018 (2)	0.023 (2)
N4	0.036 (3)	0.023 (2)	0.018 (2)	0.0039 (19)	0.0031 (19)	0.0088 (18)
O1	0.0193 (18)	0.0286 (18)	0.0219 (17)	0.0091 (15)	0.0082 (15)	0.0089 (15)
O2	0.028 (2)	0.060 (2)	0.0197 (18)	0.0253 (19)	0.0103 (16)	0.0198 (18)
O3	0.0173 (18)	0.038 (2)	0.0197 (18)	0.0067 (16)	0.0035 (15)	0.0058 (16)
O4	0.0186 (19)	0.049 (2)	0.0256 (19)	0.0095 (17)	0.0089 (16)	0.0045 (17)
O5	0.025 (2)	0.042 (2)	0.0259 (19)	0.0067 (17)	0.0073 (16)	0.0177 (17)
O6	0.043 (2)	0.0247 (18)	0.0283 (19)	0.0201 (17)	0.0185 (17)	0.0148 (16)
O7	0.032 (2)	0.0250 (17)	0.0207 (18)	0.0128 (15)	0.0115 (15)	0.0124 (15)
O8	0.031 (2)	0.0209 (17)	0.0209 (18)	0.0057 (15)	0.0036 (16)	0.0054 (15)
O9	0.0257 (19)	0.0216 (17)	0.0313 (19)	0.0120 (15)	0.0069 (16)	0.0128 (15)
O10	0.083 (4)	0.044 (2)	0.033 (2)	−0.021 (2)	0.020 (2)	0.007 (2)
O1W	0.0233 (19)	0.0369 (19)	0.0245 (18)	0.0140 (16)	0.0117 (15)	0.0134 (16)

Geometric parameters (Å, º) top

Ag1—N1ⁱ	2.239 (4)	C13—N1	1.318 (7)
Ag1—N3	2.246 (4)	C13—C14	1.374 (8)
Ag1—O7ⁱⁱ	2.306 (3)	C13—H13	0.9300
Ce1—O9ⁱⁱⁱ	2.439 (3)	C14—H14	0.9300
Ce1—O8^iv	2.483 (3)	C15—O6	1.247 (5)
Ce1—O6	2.485 (3)	C15—O7	1.264 (5)
Ce1—O3^v	2.493 (3)	C15—C16	1.503 (6)
Ce1—O2^vi	2.499 (3)	C16—C21	1.383 (6)
Ce1—O1	2.551 (3)	C16—C17	1.393 (6)
Ce1—O1W	2.576 (3)	C17—C18	1.374 (6)
Ce1—O1^vi	2.685 (3)	C17—H17	0.9300
Ce1—O7	2.690 (3)	C18—C19	1.390 (6)
C1—O2	1.237 (5)	C18—N4	1.423 (6)
C1—O1	1.274 (5)	C19—C20	1.386 (6)
C1—C2	1.503 (6)	C19—H19	0.9300
C2—C7	1.383 (6)	C20—C21	1.385 (6)
C2—C3	1.393 (6)	C20—C22	1.499 (6)
C3—C4	1.384 (6)	C21—H21	0.9300
C3—H3	0.9300	C22—O9	1.256 (5)
C4—C5	1.394 (6)	C22—O8	1.265 (5)
C4—C8	1.498 (6)	C23—O10	1.224 (6)
C5—C6	1.364 (6)	C23—N4	1.341 (6)
C5—H5	0.9300	C23—C24	1.485 (7)
C6—C7	1.382 (6)	C24—C28	1.376 (8)
C6—N2	1.416 (6)	C24—C25	1.382 (8)
C7—H7	0.9300	C25—C26	1.365 (7)
C8—O3	1.255 (6)	C25—H25	0.9300
C8—O4	1.260 (5)	C26—N3	1.343 (8)
C9—O5	1.225 (6)	C26—H26	0.9300
C9—N2	1.329 (6)	C27—N3	1.335 (7)
C9—C10	1.503 (7)	C27—C28	1.388 (7)
C10—C14	1.374 (7)	C27—H27	0.9300
C10—C11	1.378 (7)	C28—H28	0.9300
C11—C12	1.371 (7)	N2—H2	0.8600
C11—H11	0.9300	N4—H4	0.8600
C12—N1	1.324 (7)	O1W—H1WB	0.8500
C12—H12	0.9300	O1W—H1WA	0.8500

N1ⁱ—Ag1—N3	121.79 (16)	O5—C9—C10	121.0 (4)
N1ⁱ—Ag1—O7ⁱⁱ	124.05 (14)	N2—C9—C10	115.1 (4)
N3—Ag1—O7ⁱⁱ	106.74 (14)	C14—C10—C11	117.8 (5)
O9ⁱⁱⁱ—Ce1—O8^iv	133.09 (10)	C14—C10—C9	122.9 (4)
O9ⁱⁱⁱ—Ce1—O6	142.14 (11)	C11—C10—C9	119.1 (5)
O8^iv—Ce1—O6	76.29 (11)	C12—C11—C10	118.6 (5)
O9ⁱⁱⁱ—Ce1—O3^v	83.67 (11)	C12—C11—H11	120.7
O8^iv—Ce1—O3^v	141.72 (10)	C10—C11—H11	120.7
O6—Ce1—O3^v	77.23 (11)	N1—C12—C11	123.9 (5)
O9ⁱⁱⁱ—Ce1—O2^vi	77.92 (11)	N1—C12—H12	118.0
O8^iv—Ce1—O2^vi	105.14 (11)	C11—C12—H12	118.0
O6—Ce1—O2^vi	122.35 (10)	N1—C13—C14	123.5 (5)
O3^v—Ce1—O2^vi	67.59 (10)	N1—C13—H13	118.2
O9ⁱⁱⁱ—Ce1—O1	69.33 (10)	C14—C13—H13	118.2
O8^iv—Ce1—O1	69.60 (10)	C10—C14—C13	119.1 (5)
O6—Ce1—O1	113.51 (10)	C10—C14—H14	120.4
O3^v—Ce1—O1	147.60 (10)	C13—C14—H14	120.4
O2^vi—Ce1—O1	120.84 (10)	O6—C15—O7	122.8 (4)
O9ⁱⁱⁱ—Ce1—O1W	75.72 (10)	O6—C15—C16	116.8 (4)
O8^iv—Ce1—O1W	119.75 (11)	O7—C15—C16	120.4 (4)
O6—Ce1—O1W	67.66 (10)	C21—C16—C17	119.9 (4)
O3^v—Ce1—O1W	73.47 (10)	C21—C16—C15	120.7 (4)
O2^vi—Ce1—O1W	134.75 (11)	C17—C16—C15	119.4 (4)
O1—Ce1—O1W	82.50 (10)	C18—C17—C16	120.4 (4)
O9ⁱⁱⁱ—Ce1—O1^vi	79.04 (10)	C18—C17—H17	119.8
O8^iv—Ce1—O1^vi	69.80 (10)	C16—C17—H17	119.8
O6—Ce1—O1^vi	138.81 (10)	C17—C18—C19	119.6 (4)
O3^v—Ce1—O1^vi	117.28 (10)	C17—C18—N4	119.0 (4)
O2^vi—Ce1—O1^vi	49.96 (10)	C19—C18—N4	121.3 (4)
O1—Ce1—O1^vi	75.80 (10)	C20—C19—C18	120.4 (4)
O1W—Ce1—O1^vi	151.22 (9)	C20—C19—H19	119.8
O9ⁱⁱⁱ—Ce1—O7	147.39 (10)	C18—C19—H19	119.8
O8^iv—Ce1—O7	72.15 (10)	C21—C20—C19	119.7 (4)
O6—Ce1—O7	50.26 (9)	C21—C20—C22	120.2 (4)
O3^v—Ce1—O7	69.70 (10)	C19—C20—C22	120.0 (4)
O2^vi—Ce1—O7	74.76 (10)	C16—C21—C20	120.0 (4)
O1—Ce1—O7	141.32 (10)	C16—C21—H21	120.0
O1W—Ce1—O7	112.36 (9)	C20—C21—H21	120.0
O1^vi—Ce1—O7	96.35 (9)	O9—C22—O8	125.2 (4)
O9ⁱⁱⁱ—Ce1—C1^vi	77.77 (11)	O9—C22—C20	117.9 (4)
O8^iv—Ce1—C1^vi	87.39 (12)	O8—C22—C20	116.9 (4)
O6—Ce1—C1^vi	134.58 (11)	O10—C23—N4	121.8 (5)
O3^v—Ce1—C1^vi	91.94 (12)	O10—C23—C24	119.4 (5)
O2^vi—Ce1—C1^vi	24.43 (11)	N4—C23—C24	118.8 (5)
O1—Ce1—C1^vi	99.20 (11)	C28—C24—C25	117.2 (5)
O1W—Ce1—C1^vi	150.89 (12)	C28—C24—C23	124.7 (5)
O1^vi—Ce1—C1^vi	25.54 (11)	C25—C24—C23	118.1 (5)
O7—Ce1—C1^vi	84.49 (10)	C26—C25—C24	120.1 (6)
O9ⁱⁱⁱ—Ce1—Ce1^vi	70.04 (7)	C26—C25—H25	119.9
O8^iv—Ce1—Ce1^vi	63.92 (7)	C24—C25—H25	119.9
O6—Ce1—Ce1^vi	137.33 (8)	N3—C26—C25	122.7 (6)
O3^v—Ce1—Ce1^vi	144.99 (8)	N3—C26—H26	118.6
O2^vi—Ce1—Ce1^vi	84.17 (7)	C25—C26—H26	118.6
O1—Ce1—Ce1^vi	39.05 (7)	N3—C27—C28	121.9 (6)
O1W—Ce1—Ce1^vi	119.27 (7)	N3—C27—H27	119.1
O1^vi—Ce1—Ce1^vi	36.76 (6)	C28—C27—H27	119.1
O7—Ce1—Ce1^vi	123.63 (7)	C24—C28—C27	120.2 (5)
C1^vi—Ce1—Ce1^vi	60.81 (9)	C24—C28—H28	119.9
O2—C1—O1	122.0 (4)	C27—C28—H28	119.9
O2—C1—C2	119.2 (4)	C13—N1—C12	116.9 (5)
O1—C1—C2	118.8 (4)	C13—N1—Ag1ⁱ	123.5 (4)
O2—C1—Ce1^vi	56.7 (2)	C12—N1—Ag1ⁱ	116.1 (3)
O1—C1—Ce1^vi	65.3 (2)	C9—N2—C6	125.4 (4)
C2—C1—Ce1^vi	175.4 (3)	C9—N2—H2	117.3
C7—C2—C3	120.4 (4)	C6—N2—H2	117.3
C7—C2—C1	119.1 (4)	C27—N3—C26	117.9 (5)
C3—C2—C1	120.4 (4)	C27—N3—Ag1	121.3 (4)
C4—C3—C2	119.2 (4)	C26—N3—Ag1	120.8 (4)
C4—C3—H3	120.4	C23—N4—C18	122.0 (4)
C2—C3—H3	120.4	C23—N4—H4	119.0
C3—C4—C5	119.6 (4)	C18—N4—H4	119.0
C3—C4—C8	120.7 (4)	C1—O1—Ce1	152.6 (3)
C5—C4—C8	119.5 (4)	C1—O1—Ce1^vi	89.1 (3)
C6—C5—C4	120.9 (4)	Ce1—O1—Ce1^vi	104.20 (10)
C6—C5—H5	119.6	C1—O2—Ce1^vi	98.9 (3)
C4—C5—H5	119.6	C8—O3—Ce1^vii	137.7 (3)
C5—C6—C7	120.0 (4)	C15—O6—Ce1	97.7 (3)
C5—C6—N2	122.7 (4)	C15—O7—Ag1^viii	119.3 (3)
C7—C6—N2	117.2 (4)	C15—O7—Ce1	87.7 (2)
C6—C7—C2	119.9 (4)	Ag1^viii—O7—Ce1	107.58 (12)
C6—C7—H7	120.1	C22—O8—Ce1^iv	131.5 (3)
C2—C7—H7	120.1	C22—O9—Ce1^ix	129.5 (3)
O3—C8—O4	124.5 (4)	Ce1—O1W—H1WB	108.0
O3—C8—C4	118.0 (4)	Ce1—O1W—H1WA	107.2
O4—C8—C4	117.4 (4)	H1WB—O1W—H1WA	107.1
O5—C9—N2	123.9 (4)

O2—C1—C2—C7	−160.8 (4)	N1ⁱ—Ag1—N3—C26	140.5 (4)
O1—C1—C2—C7	19.1 (6)	O7ⁱⁱ—Ag1—N3—C26	−10.4 (5)
O2—C1—C2—C3	17.6 (7)	O10—C23—N4—C18	7.5 (8)
O1—C1—C2—C3	−162.4 (4)	C24—C23—N4—C18	−172.8 (4)
C7—C2—C3—C4	−0.3 (7)	C17—C18—N4—C23	124.9 (5)
C1—C2—C3—C4	−178.7 (4)	C19—C18—N4—C23	−52.0 (7)
C2—C3—C4—C5	−0.5 (7)	O2—C1—O1—Ce1	−118.1 (6)
C2—C3—C4—C8	173.2 (4)	C2—C1—O1—Ce1	62.0 (8)
C3—C4—C5—C6	0.5 (7)	Ce1^vi—C1—O1—Ce1	−120.2 (6)
C8—C4—C5—C6	−173.3 (4)	O2—C1—O1—Ce1^vi	2.1 (4)
C4—C5—C6—C7	0.3 (7)	C2—C1—O1—Ce1^vi	−177.8 (4)
C4—C5—C6—N2	177.7 (4)	O9ⁱⁱⁱ—Ce1—O1—C1	−159.6 (6)
C5—C6—C7—C2	−1.0 (7)	O8^iv—Ce1—O1—C1	43.6 (6)
N2—C6—C7—C2	−178.6 (4)	O6—Ce1—O1—C1	−20.4 (6)
C3—C2—C7—C6	1.0 (7)	O3^v—Ce1—O1—C1	−124.1 (6)
C1—C2—C7—C6	179.4 (4)	O2^vi—Ce1—O1—C1	139.5 (6)
C3—C4—C8—O3	29.7 (7)	O1W—Ce1—O1—C1	−82.1 (6)
C5—C4—C8—O3	−156.5 (4)	O1^vi—Ce1—O1—C1	117.0 (7)
C3—C4—C8—O4	−147.4 (4)	O7—Ce1—O1—C1	34.7 (7)
C5—C4—C8—O4	26.3 (6)	C1^vi—Ce1—O1—C1	127.3 (6)
O5—C9—C10—C14	139.0 (5)	Ce1^vi—Ce1—O1—C1	117.0 (7)
N2—C9—C10—C14	−38.8 (7)	O9ⁱⁱⁱ—Ce1—O1—Ce1^vi	83.44 (12)
O5—C9—C10—C11	−36.7 (7)	O8^iv—Ce1—O1—Ce1^vi	−73.38 (11)
N2—C9—C10—C11	145.5 (5)	O6—Ce1—O1—Ce1^vi	−137.43 (11)
C14—C10—C11—C12	−1.0 (8)	O3^v—Ce1—O1—Ce1^vi	118.93 (17)
C9—C10—C11—C12	174.9 (5)	O2^vi—Ce1—O1—Ce1^vi	22.50 (16)
C10—C11—C12—N1	−2.4 (10)	O1W—Ce1—O1—Ce1^vi	160.95 (12)
C11—C10—C14—C13	2.4 (8)	O1^vi—Ce1—O1—Ce1^vi	0.0
C9—C10—C14—C13	−173.4 (5)	O7—Ce1—O1—Ce1^vi	−82.34 (16)
N1—C13—C14—C10	−0.5 (10)	C1^vi—Ce1—O1—Ce1^vi	10.33 (13)
O6—C15—C16—C21	151.8 (5)	O1—C1—O2—Ce1^vi	−2.3 (5)
O7—C15—C16—C21	−28.0 (7)	C2—C1—O2—Ce1^vi	177.6 (3)
O6—C15—C16—C17	−26.0 (7)	O4—C8—O3—Ce1^vii	26.3 (8)
O7—C15—C16—C17	154.2 (5)	C4—C8—O3—Ce1^vii	−150.6 (3)
C21—C16—C17—C18	2.2 (7)	O7—C15—O6—Ce1	−13.1 (5)
C15—C16—C17—C18	180.0 (4)	C16—C15—O6—Ce1	167.0 (4)
C16—C17—C18—C19	−1.7 (8)	O9ⁱⁱⁱ—Ce1—O6—C15	−129.0 (3)
C16—C17—C18—N4	−178.7 (4)	O8^iv—Ce1—O6—C15	84.7 (3)
C17—C18—C19—C20	0.0 (7)	O3^v—Ce1—O6—C15	−67.4 (3)
N4—C18—C19—C20	176.9 (5)	O2^vi—Ce1—O6—C15	−14.7 (3)
C18—C19—C20—C21	1.2 (7)	O1—Ce1—O6—C15	144.9 (3)
C18—C19—C20—C22	−175.0 (4)	O1W—Ce1—O6—C15	−144.5 (3)
C17—C16—C21—C20	−1.0 (7)	O1^vi—Ce1—O6—C15	49.7 (4)
C15—C16—C21—C20	−178.7 (4)	O7—Ce1—O6—C15	6.7 (3)
C19—C20—C21—C16	−0.7 (7)	C1^vi—Ce1—O6—C15	12.6 (4)
C22—C20—C21—C16	175.4 (4)	Ce1^vi—Ce1—O6—C15	105.9 (3)
C21—C20—C22—O9	165.3 (4)	O6—C15—O7—Ag1^viii	121.0 (4)
C19—C20—C22—O9	−18.5 (6)	C16—C15—O7—Ag1^viii	−59.2 (5)
C21—C20—C22—O8	−15.4 (7)	O6—C15—O7—Ce1	12.0 (5)
C19—C20—C22—O8	160.8 (4)	C16—C15—O7—Ce1	−168.1 (4)
O10—C23—C24—C28	137.3 (6)	O9ⁱⁱⁱ—Ce1—O7—C15	120.7 (3)
N4—C23—C24—C28	−42.4 (8)	O8^iv—Ce1—O7—C15	−93.3 (3)
O10—C23—C24—C25	−40.9 (8)	O6—Ce1—O7—C15	−6.6 (3)
N4—C23—C24—C25	139.4 (5)	O3^v—Ce1—O7—C15	83.5 (3)
C28—C24—C25—C26	−0.8 (8)	O2^vi—Ce1—O7—C15	154.8 (3)
C23—C24—C25—C26	177.5 (5)	O1—Ce1—O7—C15	−84.5 (3)
C24—C25—C26—N3	−0.3 (9)	O1W—Ce1—O7—C15	22.2 (3)
C25—C24—C28—C27	1.4 (8)	O1^vi—Ce1—O7—C15	−159.7 (3)
C23—C24—C28—C27	−176.8 (5)	C1^vi—Ce1—O7—C15	177.6 (3)
N3—C27—C28—C24	−0.9 (9)	Ce1^vi—Ce1—O7—C15	−133.1 (3)
C14—C13—N1—C12	−2.7 (10)	O9ⁱⁱⁱ—Ce1—O7—Ag1^viii	0.7 (2)
C14—C13—N1—Ag1ⁱ	154.9 (5)	O8^iv—Ce1—O7—Ag1^viii	146.62 (14)
C11—C12—N1—C13	4.2 (10)	O6—Ce1—O7—Ag1^viii	−126.60 (18)
C11—C12—N1—Ag1ⁱ	−155.1 (5)	O3^v—Ce1—O7—Ag1^viii	−36.53 (12)
O5—C9—N2—C6	−7.6 (7)	O2^vi—Ce1—O7—Ag1^viii	34.77 (12)
C10—C9—N2—C6	170.2 (4)	O1—Ce1—O7—Ag1^viii	155.43 (12)
C5—C6—N2—C9	45.2 (7)	O1W—Ce1—O7—Ag1^viii	−97.83 (13)
C7—C6—N2—C9	−137.3 (5)	O1^vi—Ce1—O7—Ag1^viii	80.25 (12)
C28—C27—N3—C26	−0.2 (8)	C1^vi—Ce1—O7—Ag1^viii	57.59 (13)
C28—C27—N3—Ag1	−179.0 (4)	Ce1^vi—Ce1—O7—Ag1^viii	106.86 (10)
C25—C26—N3—C27	0.8 (9)	O9—C22—O8—Ce1^iv	65.6 (6)
C25—C26—N3—Ag1	179.6 (4)	C20—C22—O8—Ce1^iv	−113.6 (4)
N1ⁱ—Ag1—N3—C27	−40.7 (5)	O8—C22—O9—Ce1^ix	−41.8 (6)
O7ⁱⁱ—Ag1—N3—C27	168.3 (4)	C20—C22—O9—Ce1^ix	137.4 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5^x	0.85	2.08	2.836 (5)	147
O1W—H1WB···O4^v	0.85	2.01	2.691 (6)	137
N2—H2···O10ⁱⁱⁱ	0.86	2.01	2.788 (7)	149
N4—H4···O4^x	0.86	2.08	2.926 (6)	167

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

Experimental details

Crystal data
Chemical formula	[AgCe(C₁₄H₈N₂O₅)₂(H₂O)]
M_r	834.45
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.4869 (14), 11.1540 (15), 13.7276 (18)
α, β, γ (°)	107.853 (1), 106.778 (2), 102.885 (2)
V (Å³)	1375.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.42
Crystal size (mm)	0.20 × 0.14 × 0.10

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.643, 0.794
No. of measured, independent and observed [I > 2σ(I)] reflections	6903, 4777, 4178
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.081, 0.97
No. of reflections	4777
No. of parameters	406
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.40, −1.44

Computer programs: SMART (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···O5ⁱ	0.85	2.08	2.836 (5)	147
O1W—H1WB···O4ⁱⁱ	0.85	2.01	2.691 (6)	137
N2—H2···O10ⁱⁱⁱ	0.86	2.01	2.788 (7)	149
N4—H4···O4ⁱ	0.86	2.08	2.926 (6)	167

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

Acknowledgements

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

References

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