Poly[[hemi-μ4-oxalato-hemi-μ2-oxalato-bis­(μ3-pyrazine-2-carboxyl­ato)neodymium(III)silver(I)] monohydrate]

Feng, T.-J.; Wen, Y.-M.

doi:10.1107/S160053680902128X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m833-m834

doi:10.1107/S160053680902128X

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Poly[[hemi-μ₄-oxalato-hemi-μ₂-oxalato-bis(μ₃-pyrazine-2-carboxylato)neodymium(III)silver(I)] monohydrate]

Tian-Jun Feng ^a ^* and Yan-Mei Wen ^b

^aCollege of Mathematics, Physics and Software Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bCollege of Science, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: fengtj60@126.com

(Received 28 May 2009; accepted 4 June 2009; online 27 June 2009)

In the title coordination polymer, {[AgNd(C₅H₃N₂O₂)₂(C₂O₄)]·H₂O}_n, the Nd^III atom is coordinated in a distorted monocapped square-antiprismatic geometry by two O and two N atoms of two N,O-bidentate pyrazine-2-carboxylate (2-pzc) ligands, four O atoms of two bidentate oxalate ligands, and one O atom of a monodentate carboxylate group of a 2-pzc ligand. The Ag^I ion is coordinated in a distorted tetrahedral geometry by two N atoms from two monodentate 2-pzc ligands, one O atom from one monodentate oxalate ligand and one O atom of a bridging carboxylate group of a 2-pzc ligand. The oxalate anions link neighbouring neodymium(III) metal centres into Nd–oxalate chains, which are interconnected by Ag(2-pyz)₂ units, forming a three-dimensional polymeric framework. Intermolecular O—H⋯O and C—H⋯O hydrogen bonds are observed in the crystal structure.

Related literature

For general background to coordination polymers and open-framework materials, see: Barbour (2006 ); Kepert (2006 ); Kong et al. (2008 ); Zhang et al. (2005 ); Gheorghe et al. (2002 ). For the synthesis and crystal structure of heterometallic complexes of pyrazine-2-carboxylic acid, see: Ciurtin et al. (2002 ); Dong et al. (2000 ).

Experimental

Crystal data

[AgNd(C₅H₃N₂O₂)₂(C₂O₄)]·H₂O
M_r = 604.33
Monoclinic, P 2₁ /c
a = 10.112 (2) Å
b = 18.847 (4) Å
c = 8.0359 (16) Å
β = 95.47 (3)°
V = 1524.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 4.72 mm⁻¹
T = 293 K
0.32 × 0.26 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.241, T_max = 0.370
12072 measured reflections
2747 independent reflections
1946 reflections with I > 2σ(I)
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.111
S = 1.13
2747 reflections
244 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 1.59 e Å⁻³
Δρ_min = −1.77 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O4ⁱ	0.84	2.31	2.975 (13)	137
C3—H3⋯O1ⁱⁱ	0.93	2.34	3.221 (12)	158
C3—H3⋯O8ⁱⁱ	0.93	2.49	3.150 (13)	128
C4—H4⋯O5	0.93	2.54	3.170 (13)	125
C9—H9⋯O2ⁱⁱⁱ	0.93	2.47	3.270 (15)	145
C9—H9⋯O7^iv	0.93	2.35	2.971 (15)	124
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902128X/rz2330sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902128X/rz2330Isup2.hkl

checkCIF report

Comment top

In recent years, much research work has been focused on the design and synthesis of new potentially multifunctional heterometallic materials with useful structural properties, such as porosity, gas storage abilities and ion exchange capabilities (Barbour, 2006; Kepert, 2006; Kong et al., 2008; Zhang et al., 2005; Gheorghe et al., 2002). Pyrazine-2-carboxylate (2-pzc) is such a potential multidentate ligand, which can be used to generate high-dimensional heterometallic frameworks (Ciurtin et al., 2002; Dong et al., 2000). On the basis of above considerations, we chose pyrazine-2-carboxylic acid, mixed 4d-4f metal ions and nitric acid as our building blocks. A new three-dimensional 4d-4f coordination framework resulted from the hydrothermal treatment of Nd₂O₃, AgNO₃, oxalic acid, pyrazine-2-carboxylic acid and nitric acid in water.

As depicted in Fig. 1, the asymmetric unit of the title compound contains one neodymium(III) atom, one silver(I) atom, two crystallogaphically independent 2-pzc ligands, two halves of oxalate anions and one lattice water molecule. The neodymium(III) atom is nine-coordinated in a distorted monocapped square-antiprismatic geometry by two O and two N atoms of two N,O-bidentate pyrazine-2-carboxylate (2-pzc) ligands, four O atoms of two bidentate oxalate ligands, and one O atom of a monodentate carboxylate group of a 2-pzc ligand. Each silver(I) ion can be described as having a distorted tetrahedral coordination geometry provided by two N atoms from two monodentate 2-pzc ligands, one O atom from one monodentate oxalate ligand and one O atom of a bridging carboxylate group of a 2-pzc ligand. In the crystal structure, zigzag Nd–oxalate chains are formed via the oxalate ligands, with Nd···Nd separations of 6.290 (2) Å and 6.435 (3) Å. The interconnection of the Nd–oxalate chains and Ag(2-pyz)₂ units result in the formation of a three-dimensional polymeric structure. Intermolecular O—H···O and C—H···O hydrogen bonds involving the non-coordinated water molecules are observed in the crystal structure (Table 1, Fig. 2).

Related literature top

For general background to coordination polymers and open-framework materials, see: Barbour (2006); Kepert (2006); Kong et al. (2008); Zhang et al. (2005); Gheorghe et al. (2002). For the synthesis and crystal structure of heterometallic complexes of pyrazine-2-carboxylic acid, see: Ciurtin et al. (2002); Dong et al. (2000).

Experimental top

A mixture of Nd₂O₃ (0.168 g, 0.5 mmol), AgNO₃ (0.169 g, 1 mmol), pyrazine-2-carboxylic acid (0.124 g, 1 mmol), oxalic acid (0.09 g, 1 mmol), HNO₃ (0.12 ml) and H₂O (10 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 433 K for 3 d and then cooled to room temperature at a rate of 10 K h^-1. The colourless crystals obtained were washed with water and dried in air (yield 46% based on Nd).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity. [Symmetry codes: (i) 1 - x, 2 - y, 1 - z; (ii) 1 - x, 2 - y, -z; (iii) -1 + x,1.5 - y, -1/2 + z; (iv) -1 + x, y, z; (v) x, y, 1 + z; (vi) 2 - x, 2 - y, 1 - z.]
	Fig. 2. A partial packing diagram of the title compound showing the intermolecular hydrogen bonds as dashed lines. Hydrogen atoms not involved in hydrogen bonds are omitted.

Poly[[hemi-µ₄-oxalato-hemi-µ₂-oxalato-bis(µ₃-pyrazine-2- carboxylato)neodymium(III)silver(I)] monohydrate] top

Crystal data top

[AgNd(C₅H₃N₂O₂)₂(C₂O₄)]·H₂O	F(000) = 1148
M_r = 604.33	D_x = 2.633 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2433 reflections
a = 10.112 (2) Å	θ = 1.4–28.0°
b = 18.847 (4) Å	µ = 4.72 mm⁻¹
c = 8.0359 (16) Å	T = 293 K
β = 95.47 (3)°	Block, colourless
V = 1524.6 (5) Å³	0.32 × 0.26 × 0.21 mm
Z = 4

Data collection top

Rigaku/MSC Mercury CCD diffractometer	2747 independent reflections
Radiation source: fine-focus sealed tube	1946 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ω scans	θ_max = 25.2°, θ_min = 3.3°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −12→12
T_min = 0.241, T_max = 0.370	k = −22→22
12072 measured reflections	l = −9→9

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0182P)² + 17.3537P] where P = (F_o² + 2F_c²)/3
2747 reflections	(Δ/σ)_max = 0.028
244 parameters	Δρ_max = 1.59 e Å⁻³
3 restraints	Δρ_min = −1.77 e Å⁻³

Crystal data top

[AgNd(C₅H₃N₂O₂)₂(C₂O₄)]·H₂O	V = 1524.6 (5) Å³
M_r = 604.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.112 (2) Å	µ = 4.72 mm⁻¹
b = 18.847 (4) Å	T = 293 K
c = 8.0359 (16) Å	0.32 × 0.26 × 0.21 mm
β = 95.47 (3)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	2747 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	1946 reflections with I > 2σ(I)
T_min = 0.241, T_max = 0.370	R_int = 0.093
12072 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	3 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0182P)² + 17.3537P] where P = (F_o² + 2F_c²)/3
2747 reflections	Δρ_max = 1.59 e Å⁻³
244 parameters	Δρ_min = −1.77 e Å⁻³

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
Ag1	1.15900 (9)	0.92327 (6)	0.60684 (11)	0.0369 (3)
C1	0.9481 (10)	0.9114 (6)	0.0822 (13)	0.026 (3)
N1	0.8209 (8)	0.9101 (5)	0.0274 (10)	0.027 (2)
Nd1	0.64656 (5)	0.89514 (3)	0.26047 (7)	0.02128 (18)
O1	0.8807 (6)	0.9057 (5)	0.3541 (8)	0.0298 (19)
O1W	0.9655 (10)	0.7408 (7)	0.0126 (18)	0.099 (5)
H1W	0.9199	0.7431	0.0945	0.149*
H2W	0.9262	0.7594	−0.0734	0.149*
C2	1.0449 (10)	0.9146 (6)	−0.0258 (13)	0.029 (3)
H2	1.1337	0.9136	0.0168	0.035*
N2	1.0149 (9)	0.9190 (5)	−0.1900 (11)	0.030 (2)
O2	1.0988 (7)	0.9106 (5)	0.3253 (8)	0.035 (2)
C3	0.8869 (11)	0.9176 (7)	−0.2454 (13)	0.037 (3)
H3	0.8622	0.9195	−0.3598	0.045*
O3	1.6618 (7)	0.8233 (4)	0.5173 (9)	0.034 (2)
C4	0.7896 (11)	0.9134 (7)	−0.1356 (12)	0.034 (3)
H4	0.7006	0.9130	−0.1775	0.041*
O4	1.7098 (7)	0.7193 (4)	0.6421 (10)	0.0317 (18)
C5	0.9806 (10)	0.9093 (6)	0.2720 (13)	0.027 (3)
O5	0.5044 (7)	0.9079 (4)	−0.0030 (9)	0.0309 (18)
O6	0.3693 (7)	0.9833 (4)	−0.1510 (9)	0.0304 (19)
O7	0.5658 (7)	1.0571 (4)	0.6552 (9)	0.0274 (18)
O8	0.6685 (7)	0.9827 (4)	0.4928 (8)	0.0270 (18)
N10	1.2894 (9)	0.8232 (6)	0.6898 (12)	0.039 (3)
C11	0.4622 (10)	0.9689 (6)	−0.0439 (13)	0.026 (3)
N11	1.4588 (8)	0.7064 (5)	0.7235 (10)	0.024 (2)
C12	0.5689 (10)	1.0120 (6)	0.5441 (11)	0.022 (2)
C6	1.4972 (10)	0.7674 (6)	0.6640 (13)	0.027 (3)
C7	1.4155 (11)	0.8253 (6)	0.6552 (14)	0.031 (3)
H7	1.4498	0.8685	0.6234	0.037*
C8	1.2491 (11)	0.7609 (6)	0.7402 (15)	0.034 (3)
H8	1.1617	0.7560	0.7654	0.041*
C9	1.3340 (11)	0.7018 (7)	0.7569 (14)	0.033 (3)
H9	1.3016	0.6587	0.7922	0.040*
C10	1.6348 (11)	0.7698 (7)	0.6033 (13)	0.030 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0338 (5)	0.0520 (7)	0.0262 (4)	0.0081 (4)	0.0096 (4)	0.0043 (4)
C1	0.028 (6)	0.024 (7)	0.026 (6)	−0.007 (5)	0.006 (5)	−0.004 (5)
N1	0.028 (5)	0.035 (6)	0.018 (4)	−0.008 (4)	0.002 (4)	0.001 (4)
Nd1	0.0222 (3)	0.0239 (3)	0.0182 (3)	0.0008 (3)	0.0041 (2)	−0.0008 (3)
O1	0.009 (3)	0.063 (6)	0.017 (3)	−0.001 (4)	0.001 (3)	0.002 (4)
O1W	0.052 (7)	0.092 (11)	0.155 (12)	0.000 (6)	0.020 (7)	−0.042 (9)
C2	0.019 (5)	0.040 (8)	0.028 (6)	0.009 (5)	0.003 (4)	0.009 (5)
N2	0.032 (5)	0.037 (6)	0.022 (5)	−0.001 (4)	0.008 (4)	0.004 (4)
O2	0.021 (4)	0.066 (7)	0.017 (4)	0.004 (4)	−0.004 (3)	−0.006 (4)
C3	0.033 (7)	0.064 (10)	0.014 (5)	0.016 (6)	−0.003 (5)	−0.007 (5)
O3	0.036 (5)	0.040 (6)	0.027 (4)	−0.009 (4)	0.005 (3)	0.015 (4)
C4	0.036 (7)	0.055 (9)	0.012 (5)	−0.002 (6)	0.007 (5)	−0.007 (5)
O4	0.034 (4)	0.015 (4)	0.048 (5)	−0.001 (3)	0.013 (4)	0.008 (4)
C5	0.027 (6)	0.029 (7)	0.025 (5)	−0.008 (5)	0.010 (5)	0.006 (5)
O5	0.039 (5)	0.029 (5)	0.025 (4)	−0.004 (4)	0.000 (3)	0.003 (4)
O6	0.022 (4)	0.033 (5)	0.035 (4)	0.005 (3)	−0.007 (3)	0.002 (4)
O7	0.024 (4)	0.033 (5)	0.024 (4)	−0.001 (3)	0.000 (3)	−0.008 (4)
O8	0.026 (4)	0.034 (5)	0.021 (4)	0.007 (3)	0.006 (3)	−0.007 (3)
N10	0.029 (5)	0.043 (7)	0.043 (6)	0.004 (5)	−0.001 (5)	0.004 (5)
C11	0.024 (6)	0.028 (7)	0.027 (6)	0.002 (5)	0.003 (5)	0.008 (5)
N11	0.018 (4)	0.027 (6)	0.029 (5)	0.000 (4)	0.010 (4)	0.001 (4)
C12	0.034 (6)	0.020 (6)	0.012 (5)	0.000 (5)	0.003 (4)	−0.012 (4)
C6	0.026 (6)	0.032 (7)	0.023 (5)	0.000 (5)	0.002 (4)	0.013 (5)
C7	0.034 (7)	0.016 (7)	0.043 (7)	−0.001 (5)	0.003 (5)	0.002 (5)
C8	0.033 (6)	0.022 (7)	0.050 (7)	−0.004 (5)	0.019 (6)	0.011 (6)
C9	0.038 (7)	0.029 (7)	0.032 (6)	−0.004 (5)	0.006 (5)	0.011 (5)
C10	0.044 (7)	0.029 (8)	0.019 (5)	−0.007 (6)	0.010 (5)	−0.004 (5)

Geometric parameters (Å, º) top

Ag1—N2ⁱ	2.291 (9)	C3—H3	0.9300
Ag1—O2	2.299 (7)	O3—C10	1.267 (13)
Ag1—N10	2.360 (10)	O3—Nd1^vii	2.461 (7)
C1—N1	1.320 (13)	C4—H4	0.9300
C1—C2	1.370 (14)	O4—C10	1.240 (14)
C1—C5	1.530 (14)	O4—Nd1^viii	2.465 (7)
N1—C4	1.319 (13)	O5—C11	1.259 (13)
N1—Nd1	2.707 (8)	O6—C11	1.242 (12)
Nd1—O1	2.423 (6)	O6—Nd1ⁱⁱ	2.455 (8)
Nd1—O6ⁱⁱ	2.455 (8)	O7—C12	1.235 (11)
Nd1—O5	2.456 (7)	O7—Nd1^v	2.482 (7)
Nd1—O3ⁱⁱⁱ	2.461 (7)	O8—C12	1.252 (12)
Nd1—O4^iv	2.465 (8)	N10—C8	1.319 (15)
Nd1—O7^v	2.482 (7)	N10—C7	1.332 (14)
Nd1—O8	2.486 (7)	C11—C11ⁱⁱ	1.53 (2)
Nd1—N11^iv	2.692 (9)	N11—C9	1.317 (13)
O1—C5	1.260 (12)	N11—C6	1.318 (14)
O1W—H1W	0.8400	N11—Nd1^viii	2.692 (9)
O1W—H2W	0.8405	C12—C12^v	1.57 (2)
C2—N2	1.328 (13)	C6—C7	1.367 (15)
C2—H2	0.9300	C6—C10	1.517 (15)
N2—C3	1.329 (13)	C7—H7	0.9300
N2—Ag1^vi	2.291 (9)	C8—C9	1.406 (16)
O2—C5	1.231 (12)	C8—H8	0.9300
C3—C4	1.385 (15)	C9—H9	0.9300

N2ⁱ—Ag1—O2	124.8 (3)	N2—C2—H2	119.2
N2ⁱ—Ag1—N10	98.4 (3)	C1—C2—H2	119.2
O2—Ag1—N10	106.5 (3)	C2—N2—C3	117.0 (9)
N1—C1—C2	121.5 (10)	C2—N2—Ag1^vi	127.6 (7)
N1—C1—C5	116.3 (9)	C3—N2—Ag1^vi	115.3 (7)
C2—C1—C5	122.3 (9)	C5—O2—Ag1	120.1 (7)
C1—N1—C4	117.7 (9)	N2—C3—C4	121.1 (10)
C1—N1—Nd1	116.7 (6)	N2—C3—H3	119.5
C4—N1—Nd1	125.5 (7)	C4—C3—H3	119.5
O1—Nd1—O6ⁱⁱ	93.6 (3)	C10—O3—Nd1^vii	153.6 (7)
O1—Nd1—O5	137.2 (2)	N1—C4—C3	121.1 (10)
O6ⁱⁱ—Nd1—O5	65.6 (2)	N1—C4—H4	119.4
O1—Nd1—O3ⁱⁱⁱ	78.7 (2)	C3—C4—H4	119.4
O6ⁱⁱ—Nd1—O3ⁱⁱⁱ	144.2 (3)	C10—O4—Nd1^viii	126.5 (7)
O5—Nd1—O3ⁱⁱⁱ	139.7 (3)	O2—C5—O1	128.3 (10)
O1—Nd1—O4^iv	84.8 (3)	O2—C5—C1	117.1 (9)
O6ⁱⁱ—Nd1—O4^iv	133.5 (3)	O1—C5—C1	114.6 (9)
O5—Nd1—O4^iv	84.6 (3)	C11—O5—Nd1	118.1 (7)
O3ⁱⁱⁱ—Nd1—O4^iv	81.1 (3)	C11—O6—Nd1ⁱⁱ	118.1 (7)
O1—Nd1—O7^v	136.9 (2)	C12—O7—Nd1^v	122.0 (6)
O6ⁱⁱ—Nd1—O7^v	74.4 (2)	C12—O8—Nd1	121.6 (6)
O5—Nd1—O7^v	75.5 (2)	C8—N10—C7	114.8 (10)
O3ⁱⁱⁱ—Nd1—O7^v	87.6 (3)	C8—N10—Ag1	128.1 (8)
O4^iv—Nd1—O7^v	133.3 (2)	C7—N10—Ag1	116.0 (8)
O1—Nd1—O8	72.4 (2)	O6—C11—O5	126.5 (10)
O6ⁱⁱ—Nd1—O8	69.4 (2)	O6—C11—C11ⁱⁱ	117.6 (13)
O5—Nd1—O8	125.8 (3)	O5—C11—C11ⁱⁱ	115.8 (11)
O3ⁱⁱⁱ—Nd1—O8	75.0 (3)	C9—N11—C6	116.9 (9)
O4^iv—Nd1—O8	149.6 (2)	C9—N11—Nd1^viii	127.6 (7)
O7^v—Nd1—O8	64.6 (2)	C6—N11—Nd1^viii	115.5 (6)
O1—Nd1—N11^iv	138.7 (3)	O7—C12—O8	128.2 (10)
O6ⁱⁱ—Nd1—N11^iv	127.1 (2)	O7—C12—C12^v	116.3 (11)
O5—Nd1—N11^iv	68.0 (3)	O8—C12—C12^v	115.5 (10)
O3ⁱⁱⁱ—Nd1—N11^iv	71.9 (3)	N11—C6—C7	121.2 (10)
O4^iv—Nd1—N11^iv	62.7 (3)	N11—C6—C10	117.0 (10)
O7^v—Nd1—N11^iv	70.6 (3)	C7—C6—C10	121.9 (10)
O8—Nd1—N11^iv	124.5 (2)	N10—C7—C6	123.6 (11)
O1—Nd1—N1	61.6 (2)	N10—C7—H7	118.2
O6ⁱⁱ—Nd1—N1	71.3 (3)	C6—C7—H7	118.2
O5—Nd1—N1	76.1 (2)	N10—C8—C9	122.1 (11)
O3ⁱⁱⁱ—Nd1—N1	130.2 (3)	N10—C8—H8	118.9
O4^iv—Nd1—N1	67.3 (3)	C9—C8—H8	118.9
O7^v—Nd1—N1	142.1 (3)	N11—C9—C8	121.1 (11)
O8—Nd1—N1	115.7 (3)	N11—C9—H9	119.5
N11^iv—Nd1—N1	119.8 (3)	C8—C9—H9	119.5
C5—O1—Nd1	130.6 (6)	O4—C10—O3	126.2 (11)
H1W—O1W—H2W	111.8	O4—C10—C6	117.0 (10)
N2—C2—C1	121.5 (10)	O3—C10—C6	116.8 (10)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O4^iv	0.84	2.31	2.975 (13)	137
C3—H3···O1^vi	0.93	2.34	3.221 (12)	158
C3—H3···O8^vi	0.93	2.49	3.150 (13)	128
C4—H4···O5	0.93	2.54	3.170 (13)	125
C9—H9···O2^ix	0.93	2.47	3.270 (15)	145
C9—H9···O7^x	0.93	2.35	2.971 (15)	124

Symmetry codes: (iv) x−1, −y+3/2, z−1/2; (vi) x, y, z−1; (ix) x, −y+3/2, z+1/2; (x) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[AgNd(C₅H₃N₂O₂)₂(C₂O₄)]·H₂O
M_r	604.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.112 (2), 18.847 (4), 8.0359 (16)
β (°)	95.47 (3)
V (Å³)	1524.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.72
Crystal size (mm)	0.32 × 0.26 × 0.21

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.241, 0.370
No. of measured, independent and observed [I > 2σ(I)] reflections	12072, 2747, 1946
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.13
No. of reflections	2747
No. of parameters	244
No. of restraints	3
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0182P)² + 17.3537P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.59, −1.77

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O4ⁱ	0.84	2.31	2.975 (13)	136.8
C3—H3···O1ⁱⁱ	0.93	2.34	3.221 (12)	158
C3—H3···O8ⁱⁱ	0.93	2.49	3.150 (13)	128
C4—H4···O5	0.93	2.54	3.170 (13)	125
C9—H9···O2ⁱⁱⁱ	0.93	2.47	3.270 (15)	145
C9—H9···O7^iv	0.93	2.35	2.971 (15)	124

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

Acknowledgements

The authors acknowledge Lanzhou Jiaotong University for supporting this work.

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