Poly[aqua(μ3-5-aza­niumylisophthalato)­(μ-oxalato)neodymium(III)]

Yin, X.; Xiao, T.-T.; Fan, J.; Zheng, S.-R.; Zhang, W.-G.

doi:10.1107/S1600536812013554

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m537

doi:10.1107/S1600536812013554

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Poly[aqua(μ₃-5-azaniumylisophthalato)(μ-oxalato)neodymium(III)]

Xia Yin,^a Tian-Tian Xiao,^a Jun Fan,^a ^* Sheng-Run Zheng ^a and Wei-Guang Zhang ^a

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: fanj@scnu.edu.cn

(Received 27 March 2012; accepted 28 March 2012; online 4 April 2012)

The title compound, [Nd(C₈H₆NO₄)(C₂O₄)(H₂O)]_n, is a layer-like coordination polymer. The Nd^III ion is coordinated by four carboxylate O atoms from three bridging 5-azaniumylisophthalate (Haip) ligands, four carboxylate O atoms from two oxalate (ox) anions and one ligated water molecule in a tricapped trigonal–prismatic geometry. The Haip anion acts as a μ₃-bridge, connecting three Nd^III ions through two carboxylate groups; the ox anion adopts a bis-bidentate-bridging mode, linking two Nd^III ions. The layer framework is further extended to a three-dimensional supramolecular structure through N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For isotypic complexes, see: Liu et al. (2008 ); Yan et al. (2009 ).

Experimental

Crystal data

[Nd(C₈H₆NO₄)(C₂O₄)(H₂O)]
M_r = 430.41
Monoclinic, C 2/c
a = 20.047 (4) Å
b = 9.592 (2) Å
c = 13.670 (3) Å
β = 117.810 (2)°
V = 2325.0 (9) Å³
Z = 8
Mo Kα radiation
μ = 4.52 mm⁻¹
T = 298 K
0.28 × 0.22 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.364, T_max = 0.551
5839 measured reflections
2104 independent reflections
1792 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.056
S = 1.03
2104 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O5ⁱ	0.89	1.91	2.795 (5)	172
N1—H1C⋯O8ⁱⁱ	0.89	2.05	2.872 (5)	154
O1W—H1W⋯O3ⁱⁱⁱ	0.82	2.06	2.812 (4)	153
O1W—H2W⋯O1^iv	0.82	1.97	2.750 (4)	159
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+1, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-1, -z+{\script{1\over 2}}]$ ; (iv) $[-x, y, -z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013554/ng5259sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013554/ng5259Isup2.hkl

checkCIF report

Comment top

The 5-aminoisophthalate (aip) anion adopts various coordination modes in lanthanide complexes. In this work, we present the synthesis and structure of a new neodymium coordination polymer with 5-aminoisophthalate and oxalate, [Nd(Haip)(ox)(H₂O)], which is isostructural with those reported previously (Liu et al., 2008; Yan et al., 2009).

In the title compound, the asymmetric unit comprises one Nd^III ion, one Haip ligand, one oxalate anion and one ligated water molecule (Fig. 1). The neodymium ion is nine-coordinated by four carboxylate O atoms [O1, O2, O3ⁱ, and O4ⁱⁱ, symmetry codes: (i) -x, 1 - y, -z; (ii) x, -1 + y, z] from three Haip ligands, four carboxylate O atoms [O5, O6, O7ⁱⁱⁱ, and O8ⁱⁱⁱ, symmetry codes: (iii) 1/2 - x, 1/2 + y, 1/2 - z] from two oxalate ions and one coordinated water molecule. The geometry is a tricapped trigonal prism configuration (Fig. 2). The Nd—O bond distances are in the range of 2.417 (3)–2.603 (3) Å.

The Haip anion acts as µ₃-bridge to connect three Nd^III ions through two carboxylate groups and the amino group exists as an –NH₃⁺ unit. The oxalate anion adopts a bis-bidenatate-bridging mode to link two Nd^III ions with a Nd···Nd separation of 6.3821 (10) Å. The coordination of the metal ions and organic ligands (Haip and ox) results in the formation of a layer-like framework in the ab plane (Fig. 3).

In addition, there are O–H···O [O···O distances, 2.750 (4) and 2.812 (4) Å] and N–H···O hydrogen bonds (Table 1). The layers are further linked via these hydrogen bonds to form a three-dimensional supramolecular architecture (Fig. 4).

Related literature top

For isotypic complexes, see: Liu et al. (2008); Yan et al. (2009).

Experimental top

A mixture of 5-aminoisophthalic acid (0.50 mmol, 90.6 mg), Nd(NO₃)₃.6H₂O (0.30 mmol, 131.5 mg,) oxalic acid (0.50 mmol, 45.0 mg) and 10 ml H₂O was sealed in a 15 ml Teflon-lined stainless steel reactor and heated at 423 K under autogenous pressure for 72 h. After the sample had been slowly cooled to room temperature at a rate of 5 K/h, block-shaped pale-purple crystals were isolated (yield 52%). IR (KBr pellet, ν cm^-1): 3423 (m), 1631 (s), 1570 (s), 1466 (m), 1394 (s), 1326 (m), 1116 (m), 914 (w), 769 (s), 596 (m).

Computing details top

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

Figures top

	Fig. 1. A fragment of the polymeric structure, with displacement ellipsoids drawn at the 30% probability level. [Symmetry codes: (i) -x, 1 - y, -z; (ii) x, -1 + y, z; (iii) 1/2 - x, 1/2 + y, 1/2 - z].
	Fig. 2. Geometry of the nine-coordinated Nd^III ion in the title compound.
	Fig. 3. A packing diagram of the title compound, showing a layer-like structure in the ab plane.
	Fig. 4. . A packing diagram, showing a three-dimensional supramolecular network driven by hydrogen bonds (dashed lines).

Poly[aqua(µ₃-5-azaniumylisophthalato)(µ-oxalato)neodymium(III)] top

Crystal data top

[Nd(C₈H₆NO₄)(C₂O₄)(H₂O)]	F(000) = 1656
M_r = 430.41	D_x = 2.459 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -c 2yc	Cell parameters from 2699 reflections
a = 20.047 (4) Å	θ = 2.3–28.1°
b = 9.592 (2) Å	µ = 4.52 mm⁻¹
c = 13.670 (3) Å	T = 298 K
β = 117.810 (2)°	Block, pale-purple
V = 2325.0 (9) Å³	0.28 × 0.22 × 0.15 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	2104 independent reflections
Radiation source: fine-focus sealed tube	1792 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scan	θ_max = 25.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −24→23
T_min = 0.364, T_max = 0.551	k = −6→11
5839 measured reflections	l = −16→15

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.056	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0254P)²] where P = (F_o² + 2F_c²)/3
2104 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Nd(C₈H₆NO₄)(C₂O₄)(H₂O)]	V = 2325.0 (9) Å³
M_r = 430.41	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.047 (4) Å	µ = 4.52 mm⁻¹
b = 9.592 (2) Å	T = 298 K
c = 13.670 (3) Å	0.28 × 0.22 × 0.15 mm
β = 117.810 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2104 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1792 reflections with I > 2σ(I)
T_min = 0.364, T_max = 0.551	R_int = 0.033
5839 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.056	H-atom parameters constrained
S = 1.03	Δρ_max = 0.71 e Å⁻³
2104 reflections	Δρ_min = −0.53 e Å⁻³
191 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
C1	0.0410 (3)	0.3120 (5)	0.1508 (3)	0.0193 (10)
C2	−0.0121 (3)	0.4328 (4)	0.1225 (4)	0.0191 (10)
C3	−0.0873 (3)	0.4068 (5)	0.0894 (3)	0.0202 (10)
H3	−0.1043	0.3155	0.0846	0.024*
C4	−0.1372 (2)	0.5164 (4)	0.0632 (3)	0.0172 (10)
C5	−0.1136 (2)	0.6520 (4)	0.0653 (3)	0.0184 (10)
H5	−0.1480	0.7249	0.0465	0.022*
C6	−0.0386 (2)	0.6794 (4)	0.0956 (3)	0.0154 (9)
C7	0.0131 (2)	0.5702 (4)	0.1271 (3)	0.0181 (10)
H7	0.0639	0.5882	0.1511	0.022*
C8	−0.0168 (3)	0.8255 (5)	0.0841 (4)	0.0200 (10)
C9	0.2271 (2)	−0.2176 (5)	0.1774 (4)	0.0180 (10)
C10	0.2346 (2)	−0.2223 (5)	0.2950 (4)	0.0191 (10)
N1	−0.2164 (2)	0.4895 (4)	0.0294 (3)	0.0238 (9)
H1A	−0.2248	0.3981	0.0228	0.036*
H1B	−0.2448	0.5306	−0.0353	0.036*
H1C	−0.2282	0.5235	0.0800	0.036*
Nd1	0.131834 (12)	0.06274 (2)	0.184227 (18)	0.01456 (9)
O1	0.01407 (17)	0.1908 (3)	0.1433 (3)	0.0254 (7)
O2	0.10891 (17)	0.3304 (3)	0.1781 (2)	0.0278 (8)
O3	−0.06874 (17)	0.9033 (3)	0.0145 (2)	0.0203 (7)
O4	0.05001 (17)	0.8623 (3)	0.1427 (3)	0.0258 (8)
O5	0.20791 (17)	−0.1221 (3)	0.3242 (2)	0.0232 (7)
O6	0.19047 (18)	−0.1178 (3)	0.1175 (2)	0.0240 (7)
O7	0.25959 (17)	−0.3114 (3)	0.1530 (2)	0.0264 (8)
O8	0.26728 (17)	−0.3267 (3)	0.3532 (2)	0.0235 (7)
O1W	0.10490 (18)	0.0638 (3)	0.3446 (3)	0.0276 (8)
H1W	0.1092	0.0089	0.3930	0.041*
H2W	0.0717	0.1186	0.3396	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.026 (3)	0.018 (3)	0.015 (2)	0.004 (2)	0.011 (2)	0.0035 (19)
C2	0.023 (2)	0.017 (3)	0.019 (2)	0.008 (2)	0.010 (2)	0.0066 (19)
C3	0.025 (3)	0.018 (3)	0.018 (2)	−0.0024 (19)	0.011 (2)	0.0026 (19)
C4	0.019 (2)	0.015 (2)	0.016 (2)	−0.0019 (19)	0.0066 (19)	−0.0008 (19)
C5	0.018 (2)	0.014 (2)	0.022 (2)	0.0044 (18)	0.008 (2)	0.0010 (19)
C6	0.015 (2)	0.015 (2)	0.017 (2)	−0.0006 (18)	0.0076 (19)	0.0005 (19)
C7	0.014 (2)	0.021 (3)	0.018 (2)	0.0002 (19)	0.0065 (19)	−0.0005 (19)
C8	0.025 (3)	0.017 (3)	0.021 (2)	−0.002 (2)	0.014 (2)	−0.002 (2)
C9	0.010 (2)	0.018 (3)	0.023 (2)	−0.0036 (18)	0.007 (2)	−0.006 (2)
C10	0.016 (2)	0.019 (3)	0.023 (2)	−0.0017 (19)	0.010 (2)	0.002 (2)
N1	0.023 (2)	0.018 (2)	0.028 (2)	−0.0009 (17)	0.0108 (18)	−0.0036 (17)
Nd1	0.01452 (14)	0.01069 (14)	0.01771 (14)	0.00055 (10)	0.00688 (10)	0.00072 (10)
O1	0.0239 (18)	0.0142 (18)	0.040 (2)	0.0040 (14)	0.0170 (16)	0.0043 (15)
O2	0.0174 (18)	0.0239 (19)	0.039 (2)	0.0046 (14)	0.0104 (15)	0.0028 (15)
O3	0.0251 (18)	0.0131 (17)	0.0175 (16)	0.0024 (13)	0.0055 (14)	0.0022 (13)
O4	0.0208 (18)	0.0158 (18)	0.0324 (18)	−0.0050 (14)	0.0054 (15)	0.0014 (14)
O5	0.0280 (19)	0.0191 (17)	0.0234 (17)	0.0092 (14)	0.0128 (15)	−0.0022 (14)
O6	0.0337 (19)	0.0192 (18)	0.0240 (18)	0.0091 (15)	0.0175 (16)	0.0057 (14)
O7	0.0238 (18)	0.027 (2)	0.0259 (17)	0.0093 (15)	0.0096 (15)	−0.0052 (15)
O8	0.0238 (18)	0.0200 (19)	0.0296 (18)	0.0066 (14)	0.0149 (15)	0.0089 (14)
O1W	0.0317 (19)	0.028 (2)	0.0304 (19)	0.0082 (15)	0.0204 (16)	0.0084 (14)

Geometric parameters (Å, º) top

C1—O2	1.245 (5)	C9—C10	1.544 (6)
C1—O1	1.265 (5)	C10—O5	1.253 (5)
C1—C2	1.498 (6)	C10—O8	1.256 (5)
C2—C3	1.379 (6)	N1—H1A	0.8900
C2—C7	1.402 (6)	N1—H1B	0.8900
C3—C4	1.379 (6)	N1—H1C	0.8900
C3—H3	0.9300	Nd1—O4ⁱ	2.417 (3)
C4—C5	1.380 (6)	Nd1—O3ⁱⁱ	2.425 (3)
C4—N1	1.454 (5)	Nd1—O1	2.482 (3)
C5—C6	1.387 (6)	Nd1—O1W	2.491 (3)
C5—H5	0.9300	Nd1—O6	2.492 (3)
C6—C7	1.392 (6)	Nd1—O5	2.532 (3)
C6—C8	1.497 (6)	Nd1—O8ⁱⁱⁱ	2.538 (3)
C7—H7	0.9300	Nd1—O7ⁱⁱⁱ	2.575 (3)
C8—O4	1.248 (5)	Nd1—O2	2.603 (3)
C8—O3	1.274 (5)	O1W—H1W	0.8182
C9—O7	1.244 (5)	O1W—H2W	0.8249
C9—O6	1.252 (5)

O2—C1—O1	121.3 (4)	O4ⁱ—Nd1—O6	75.26 (11)
O2—C1—C2	120.9 (4)	O3ⁱⁱ—Nd1—O6	76.82 (10)
O1—C1—C2	117.7 (4)	O1—Nd1—O6	145.34 (10)
C3—C2—C7	120.1 (4)	O1W—Nd1—O6	131.15 (10)
C3—C2—C1	118.7 (4)	O4ⁱ—Nd1—O5	73.98 (10)
C7—C2—C1	121.2 (4)	O3ⁱⁱ—Nd1—O5	139.16 (10)
C4—C3—C2	119.8 (4)	O1—Nd1—O5	133.70 (10)
C4—C3—H3	120.1	O1W—Nd1—O5	68.83 (10)
C2—C3—H3	120.1	O6—Nd1—O5	64.51 (9)
C3—C4—C5	120.9 (4)	O4ⁱ—Nd1—O8ⁱⁱⁱ	143.36 (10)
C3—C4—N1	120.0 (4)	O3ⁱⁱ—Nd1—O8ⁱⁱⁱ	76.48 (10)
C5—C4—N1	119.1 (4)	O1—Nd1—O8ⁱⁱⁱ	120.75 (10)
C4—C5—C6	119.9 (4)	O1W—Nd1—O8ⁱⁱⁱ	134.10 (10)
C4—C5—H5	120.0	O6—Nd1—O8ⁱⁱⁱ	70.15 (10)
C6—C5—H5	120.0	O5—Nd1—O8ⁱⁱⁱ	100.92 (10)
C5—C6—C7	119.7 (4)	O4ⁱ—Nd1—O7ⁱⁱⁱ	141.60 (10)
C5—C6—C8	118.4 (4)	O3ⁱⁱ—Nd1—O7ⁱⁱⁱ	133.95 (10)
C7—C6—C8	121.7 (4)	O1—Nd1—O7ⁱⁱⁱ	107.11 (10)
C6—C7—C2	119.5 (4)	O1W—Nd1—O7ⁱⁱⁱ	71.34 (10)
C6—C7—H7	120.2	O6—Nd1—O7ⁱⁱⁱ	106.82 (10)
C2—C7—H7	120.2	O5—Nd1—O7ⁱⁱⁱ	72.95 (10)
O4—C8—O3	124.9 (4)	O8ⁱⁱⁱ—Nd1—O7ⁱⁱⁱ	63.03 (10)
O4—C8—C6	118.4 (4)	O4ⁱ—Nd1—O2	133.39 (10)
O3—C8—C6	116.7 (4)	O3ⁱⁱ—Nd1—O2	80.76 (9)
O7—C9—O6	126.7 (4)	O1—Nd1—O2	50.92 (10)
O7—C9—C10	116.8 (4)	O1W—Nd1—O2	85.21 (10)
O6—C9—C10	116.5 (4)	O6—Nd1—O2	141.25 (10)
O5—C10—O8	125.7 (4)	O5—Nd1—O2	138.60 (9)
O5—C10—C9	117.5 (4)	O8ⁱⁱⁱ—Nd1—O2	74.13 (10)
O8—C10—C9	116.8 (4)	O7ⁱⁱⁱ—Nd1—O2	68.31 (10)
C4—N1—H1A	109.5	C1—O1—Nd1	96.4 (3)
C4—N1—H1B	109.5	C1—O2—Nd1	91.2 (3)
H1A—N1—H1B	109.5	C8—O3—Nd1ⁱⁱ	137.1 (3)
C4—N1—H1C	109.5	C8—O4—Nd1^iv	141.5 (3)
H1A—N1—H1C	109.5	C10—O5—Nd1	119.5 (3)
H1B—N1—H1C	109.5	C9—O6—Nd1	121.7 (3)
O4ⁱ—Nd1—O3ⁱⁱ	84.35 (10)	C9—O7—Nd1^v	116.4 (3)
O4ⁱ—Nd1—O1	82.57 (10)	C10—O8—Nd1^v	115.8 (3)
O3ⁱⁱ—Nd1—O1	74.75 (10)	Nd1—O1W—H1W	136.4
O4ⁱ—Nd1—O1W	78.94 (10)	Nd1—O1W—H2W	115.3
O3ⁱⁱ—Nd1—O1W	140.51 (11)	H1W—O1W—H2W	104.8
O1—Nd1—O1W	67.81 (10)

O2—C1—C2—C3	178.0 (4)	O4ⁱ—Nd1—O2—C1	2.9 (3)
O1—C1—C2—C3	−0.4 (6)	O3ⁱⁱ—Nd1—O2—C1	76.0 (3)
O2—C1—C2—C7	−0.7 (7)	O1—Nd1—O2—C1	−1.9 (2)
O1—C1—C2—C7	−179.0 (4)	O1W—Nd1—O2—C1	−67.0 (3)
C7—C2—C3—C4	−1.5 (7)	O6—Nd1—O2—C1	131.1 (3)
C1—C2—C3—C4	179.8 (4)	O5—Nd1—O2—C1	−117.0 (3)
C2—C3—C4—C5	2.7 (7)	O8ⁱⁱⁱ—Nd1—O2—C1	154.4 (3)
C2—C3—C4—N1	−179.3 (4)	O7ⁱⁱⁱ—Nd1—O2—C1	−138.8 (3)
C3—C4—C5—C6	−1.0 (6)	O4—C8—O3—Nd1ⁱⁱ	100.8 (5)
N1—C4—C5—C6	−178.9 (4)	C6—C8—O3—Nd1ⁱⁱ	−79.5 (5)
C4—C5—C6—C7	−2.1 (6)	O3—C8—O4—Nd1^iv	2.2 (8)
C4—C5—C6—C8	172.9 (4)	C6—C8—O4—Nd1^iv	−177.5 (3)
C5—C6—C7—C2	3.3 (6)	O8—C10—O5—Nd1	−173.2 (3)
C8—C6—C7—C2	−171.5 (4)	C9—C10—O5—Nd1	7.0 (5)
C3—C2—C7—C6	−1.5 (7)	O4ⁱ—Nd1—O5—C10	75.8 (3)
C1—C2—C7—C6	177.2 (4)	O3ⁱⁱ—Nd1—O5—C10	15.1 (4)
C5—C6—C8—O4	156.3 (4)	O1—Nd1—O5—C10	138.4 (3)
C7—C6—C8—O4	−28.9 (6)	O1W—Nd1—O5—C10	159.9 (3)
C5—C6—C8—O3	−23.5 (6)	O6—Nd1—O5—C10	−5.2 (3)
C7—C6—C8—O3	151.4 (4)	O8ⁱⁱⁱ—Nd1—O5—C10	−66.8 (3)
O7—C9—C10—O5	173.9 (4)	O7ⁱⁱⁱ—Nd1—O5—C10	−124.0 (3)
O6—C9—C10—O5	−4.4 (6)	O2—Nd1—O5—C10	−145.2 (3)
O7—C9—C10—O8	−6.0 (6)	O7—C9—O6—Nd1	−178.6 (3)
O6—C9—C10—O8	175.8 (4)	C10—C9—O6—Nd1	−0.6 (5)
O2—C1—O1—Nd1	−3.5 (4)	O4ⁱ—Nd1—O6—C9	−76.3 (3)
C2—C1—O1—Nd1	174.9 (3)	O3ⁱⁱ—Nd1—O6—C9	−163.8 (3)
O4ⁱ—Nd1—O1—C1	−174.7 (3)	O1—Nd1—O6—C9	−128.3 (3)
O3ⁱⁱ—Nd1—O1—C1	−88.6 (3)	O1W—Nd1—O6—C9	−15.8 (4)
O1W—Nd1—O1—C1	104.3 (3)	O5—Nd1—O6—C9	2.7 (3)
O6—Nd1—O1—C1	−124.5 (3)	O8ⁱⁱⁱ—Nd1—O6—C9	116.0 (3)
O5—Nd1—O1—C1	125.9 (2)	O7ⁱⁱⁱ—Nd1—O6—C9	63.8 (3)
O8ⁱⁱⁱ—Nd1—O1—C1	−24.9 (3)	O2—Nd1—O6—C9	139.9 (3)
O7ⁱⁱⁱ—Nd1—O1—C1	43.4 (3)	O6—C9—O7—Nd1^v	156.9 (4)
O2—Nd1—O1—C1	1.8 (2)	C10—C9—O7—Nd1^v	−21.2 (5)
O1—C1—O2—Nd1	3.3 (4)	O5—C10—O8—Nd1^v	−149.6 (4)
C2—C1—O2—Nd1	−175.0 (4)	C9—C10—O8—Nd1^v	30.3 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O5^vi	0.89	1.91	2.795 (5)	172
N1—H1C···O8^vii	0.89	2.05	2.872 (5)	154
O1W—H1W···O3^viii	0.82	2.06	2.812 (4)	153
O1W—H2W···O1^ix	0.82	1.97	2.750 (4)	159

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

Experimental details

Crystal data
Chemical formula	[Nd(C₈H₆NO₄)(C₂O₄)(H₂O)]
M_r	430.41
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	20.047 (4), 9.592 (2), 13.670 (3)
β (°)	117.810 (2)
V (Å³)	2325.0 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.52
Crystal size (mm)	0.28 × 0.22 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.364, 0.551
No. of measured, independent and observed [I > 2σ(I)] reflections	5839, 2104, 1792
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.056, 1.03
No. of reflections	2104
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.53

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O5ⁱ	0.89	1.91	2.795 (5)	171.5
N1—H1C···O8ⁱⁱ	0.89	2.05	2.872 (5)	154.1
O1W—H1W···O3ⁱⁱⁱ	0.82	2.06	2.812 (4)	152.8
O1W—H2W···O1^iv	0.82	1.97	2.750 (4)	158.5

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

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (grant Nos. 21171059 and 21003053) and Guangdong Science and Technology Department (grant Nos. 2010B090300031 and 2011B010400023).

References

Bruker (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, C. B., Wen, H. L., Tan, S. S. & Yi, X. G. (2008). J. Mol. Struct. 879, 25–29. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yan, L.-S., Huang, D.-H. & Liu, C.-B. (2009). Acta Cryst. E65, m750. Web of Science CSD CrossRef IUCr Journals Google Scholar