catena-Poly[[[tetraaqua(3,5-dinitro-4-oxidopyridine N-oxide-κO1)neodymium(III)]-μ-oxalato-κ4O1,O2:O1′,O2′] tetrahydrate]

Han, Y.-F.; Ng, S.W.

doi:10.1107/S1600536810041139

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages m1431-m1432

https://doi.org/10.1107/S1600536810041139

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catena-Poly[[[tetraaqua(3,5-dinitro-4-oxidopyridine N-oxide-κO¹)neodymium(III)]-μ-oxalato-κ⁴O¹,O²:O^1′,O^2′] tetrahydrate]

Yin-Feng Han ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Science, Baoji 721013, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 September 2010; accepted 13 October 2010; online 23 October 2010)

In the title coordination polymer, {[Nd(C₅H₂N₃O₆)(C₂O₄)(H₂O)₄]·4H₂O}_n, the oxalate dianions link adjacent nine-coordinate, tricapped trigonal-prismatic Nd(III) atoms into a chain running along the b axis. The 3,5-dinitropyridin-4-oxido N-oxide ligand is formally a zwitterionic anion; the anion binds to the metal atom through the N-oxide O atom. The chains are connected into a three-dimensional network by O—H⋯O hydrogen bonds involving the coordinated and uncoordinated water molecules.

Related literature

For a related Nd(III) structure, see: Wang et al. (2010 ).

Experimental

Crystal data

[Nd(C₅H₂N₃O₆)(C₂O₄)(H₂O)₄]·4H₂O
M_r = 576.48
Triclinic, $[P \overline 1]$
a = 6.7695 (7) Å
b = 9.9695 (11) Å
c = 14.6269 (16) Å
α = 73.719 (1)°
β = 88.137 (1)°
γ = 76.693 (1)°
V = 921.58 (17) Å³
Z = 2
Mo Kα radiation
μ = 2.92 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.429, T_max = 0.868
7952 measured reflections
4147 independent reflections
4005 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.050
S = 1.06
4147 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Table 1
Selected bond lengths (Å)

Nd1—O1	2.5266 (16)
Nd1—O7	2.5124 (16)
Nd1—O8ⁱ	2.4972 (16)
Nd1—O9	2.5243 (16)
Nd1—O10ⁱⁱ	2.4897 (16)
Nd1—O1W	2.4798 (16)
Nd1—O2W	2.5080 (17)
Nd1—O3W	2.5241 (17)
Nd1—O4W	2.5153 (16)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O4ⁱⁱⁱ	0.84	1.99	2.809 (2)	166
O1w—H12⋯O5w	0.84	1.89	2.736 (3)	178
O2w—H21⋯O8^iv	0.84	2.06	2.890 (2)	174
O2w—H22⋯O7w	0.84	1.97	2.806 (3)	174
O3w—H31⋯O7^iv	0.85	2.07	2.908 (2)	170
O3w—H32⋯O8w^iv	0.84	2.03	2.841 (3)	161
O4w—H41⋯O4ⁱⁱⁱ	0.84	1.97	2.759 (2)	155
O4w—H42⋯O6w^v	0.83	2.02	2.851 (3)	177
O5w—H51⋯O6w	0.84	2.06	2.893 (3)	171
O5w—H52⋯O3ⁱⁱⁱ	0.82	2.43	2.956 (3)	123
O6w—H61⋯O10	0.84	2.09	2.915 (3)	168
O6w—H62⋯O8wⁱⁱ	0.85	2.13	2.942 (3)	160
O7w—H71⋯O1ⁱⁱ	0.84	1.93	2.766 (2)	172
O7w—H72⋯O9^vi	0.84	2.13	2.953 (2)	168
O8w—H81⋯O6ⁱⁱ	0.85	2.46	3.310 (4)	174
O8w—H82⋯O7w	0.84	2.02	2.816 (3)	160
Symmetry codes: (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z+2; (iv) -x+2, -y+1, -z+1; (v) x, y-1, z; (vi) -x+2, -y+2, -z+1.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810041139/xu5029sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041139/xu5029Isup2.hkl

checkCIF report

Comment top

Lanthanum(III) oxalates adopt open-framework architectures whose cavities are occupied by the templating agent, typically an ammonium counterion. The reaction of neodymium nitrate and adipic acid in the presence of 3,5-dinitro-4-hydroxypyridine N-oxide gave an unexpected neodymium oxalate, whose positive charge is balanced by the deprotonated 3,5-dinitropyridin-4-olate-N-oxide unit. The oxalate part of the coordination polymer, [Nd(H₂O)₄(C₅H₂N₃O₆)(C₂O₄)^.H₂O]_n (Scheme I, Fig. 1), links adjacent nine-coordinate, tricapped-trigonal-prismatic Nd(III) centers (Fig. 2) into a linear chain running along the b axis of the triclinic unit cell. The 3,5-dinitropyridin-4-olate-N-oxide part is formally a zwitterionic anion; the anion binds through the N-oxide O atom. The chains are connected by O–H···O hydrogen bonds that involve the coordinated and lattice water molecules into a three-dimensional network.

This study continues from the only report of a metal derivative of 3,5-dinitro-4-hydroxypyridine N-oxide; the deprotonated ligand is also unidentate in the tris-ethanol adduct of the same metal (Wang et al., 2010).

Related literature top

For a related Nd(III) structure, see: Wang et al. (2010).

Experimental top

3,5-Dinitro-4-hydroxypyridine N-oxide (0.183 g), a commercially available chemical, was dissolved in water (25 ml) at 333 K. Neodymium nitrate hexahydrate (0.441 g) was added and the mixture heated for 6 h. Adipic acid (0.091 g) was added and the mixture heated for another 2 h. The solution was filtered and the water removed by evaporation. The residue was recrystallzed from ethanol solution to furnish violet-colored prisms. These were washed with water.

Structure description top

For a related Nd(III) structure, see: Wang et al. (2010).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of the chain motif of [Nd(H₂O)₄(C₅H₂N₃O₆)(C₂O₄)^.H₂O]_n at the 50% probability level; hydrogen atoms are shown as spheres of arbitrary radius. Symmetry codes: i = 1 - x, 1 - y, 1 - z; ii = 1 - y, 2 - y, 1 - z.
	Fig. 2. Nine-coordinate geometry of Nd.

catena-Poly[[[tetraaqua(3,5-dinitro-4-oxidopyridine N-oxide-κO¹)neodymium(III)]-µ-oxalato- κ⁴O¹,O²:O^1',O^2'] tetrahydrate] top

Crystal data top

[Nd(C₅H₂N₃O₆)(C₂O₄)(H₂O)₄]·4H₂O	Z = 2
M_r = 576.48	F(000) = 570
Triclinic, P1	D_x = 2.077 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7695 (7) Å	Cell parameters from 6995 reflections
b = 9.9695 (11) Å	θ = 2.3–28.2°
c = 14.6269 (16) Å	µ = 2.92 mm⁻¹
α = 73.719 (1)°	T = 293 K
β = 88.137 (1)°	Prism, violet
γ = 76.693 (1)°	0.35 × 0.25 × 0.05 mm
V = 921.58 (17) Å³

Data collection top

Bruker SMART APEX diffraractometer diffractometer	4147 independent reflections
Radiation source: fine-focus sealed tube	4005 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
φ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.429, T_max = 0.868	k = −12→12
7952 measured reflections	l = −18→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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.050	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.031P)² + 0.4577P] where P = (F_o² + 2F_c²)/3
4147 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.94 e Å⁻³

Crystal data top

[Nd(C₅H₂N₃O₆)(C₂O₄)(H₂O)₄]·4H₂O	γ = 76.693 (1)°
M_r = 576.48	V = 921.58 (17) Å³
Triclinic, P1	Z = 2
a = 6.7695 (7) Å	Mo Kα radiation
b = 9.9695 (11) Å	µ = 2.92 mm⁻¹
c = 14.6269 (16) Å	T = 293 K
α = 73.719 (1)°	0.35 × 0.25 × 0.05 mm
β = 88.137 (1)°

Data collection top

Bruker SMART APEX diffraractometer diffractometer	4147 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4005 reflections with I > 2σ(I)
T_min = 0.429, T_max = 0.868	R_int = 0.015
7952 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.050	H-atom parameters constrained
S = 1.06	Δρ_max = 0.48 e Å⁻³
4147 reflections	Δρ_min = −0.94 e Å⁻³
262 parameters

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

	x	y	z	U_iso*/U_eq
Nd1	0.671311 (14)	0.671999 (10)	0.625076 (7)	0.01518 (5)
N1	0.3029 (3)	0.7237 (2)	0.78523 (13)	0.0226 (4)
N2	0.2172 (3)	0.3827 (2)	0.93382 (15)	0.0299 (4)
N3	0.2733 (4)	0.8438 (2)	1.00008 (16)	0.0403 (6)
O1	0.3422 (3)	0.77791 (18)	0.69178 (11)	0.0261 (3)
O1W	0.7817 (3)	0.69793 (18)	0.77798 (11)	0.0292 (4)
H11	0.7867	0.6312	0.8283	0.044*
H12	0.7757	0.7744	0.7930	0.044*
O2	0.2029 (5)	0.3315 (3)	0.86815 (16)	0.0645 (8)
O2W	0.9719 (3)	0.75337 (19)	0.54317 (15)	0.0383 (4)
H21	1.0937	0.7091	0.5550	0.057*
H22	0.9657	0.8251	0.4958	0.057*
O3	0.2085 (4)	0.3157 (2)	1.01719 (14)	0.0471 (5)
O3W	1.0000 (3)	0.48281 (19)	0.66002 (13)	0.0340 (4)
H31	1.0649	0.4802	0.6098	0.051*
H32	1.0039	0.3978	0.6927	0.051*
O4	0.2421 (3)	0.5451 (2)	1.07188 (12)	0.0361 (4)
O4W	0.6382 (3)	0.44826 (18)	0.75126 (12)	0.0284 (4)
H41	0.6831	0.4230	0.8078	0.043*
H42	0.6051	0.3790	0.7399	0.043*
O5	0.2961 (8)	0.7979 (3)	1.08425 (18)	0.1165 (17)
O5W	0.7576 (5)	0.9490 (3)	0.82384 (19)	0.0745 (9)
H51	0.6753	1.0248	0.7945	0.112*
H52	0.7493	0.9288	0.8820	0.112*
O6	0.2434 (7)	0.9714 (3)	0.96151 (19)	0.0894 (12)
O6W	0.5130 (3)	1.2177 (2)	0.70856 (15)	0.0448 (5)
H61	0.5106	1.2141	0.6518	0.067*
H62	0.4016	1.2031	0.7331	0.067*
O7	0.7357 (2)	0.5438 (2)	0.49783 (13)	0.0303 (4)
O7W	0.9661 (3)	0.98025 (19)	0.37762 (14)	0.0361 (4)
H71	0.8719	1.0540	0.3619	0.054*
H72	1.0779	1.0030	0.3739	0.054*
O8	0.6186 (2)	0.41980 (19)	0.41502 (13)	0.0270 (3)
O8W	0.9041 (4)	0.8190 (2)	0.25538 (16)	0.0513 (6)
H81	0.8735	0.8759	0.1999	0.077*
H82	0.9535	0.8569	0.2908	0.077*
O9	0.6495 (2)	0.93475 (16)	0.60571 (11)	0.0248 (3)
O10	0.5087 (3)	1.16112 (17)	0.52372 (12)	0.0306 (4)
C1	0.2625 (3)	0.5922 (2)	0.81517 (16)	0.0227 (4)
H1	0.2476	0.5435	0.7710	0.027*
C2	0.2433 (3)	0.5296 (2)	0.91041 (16)	0.0222 (4)
C3	0.2536 (3)	0.6000 (2)	0.98472 (16)	0.0236 (4)
C4	0.2774 (4)	0.7458 (2)	0.94198 (16)	0.0260 (5)
C5	0.3056 (4)	0.8018 (2)	0.84657 (17)	0.0260 (5)
H5	0.3266	0.8943	0.8243	0.031*
C6	0.6016 (3)	0.4897 (2)	0.47487 (15)	0.0197 (4)
C7	0.5458 (3)	1.0272 (2)	0.53784 (15)	0.0209 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Nd1	0.01768 (7)	0.01469 (7)	0.01310 (6)	−0.00390 (4)	−0.00032 (4)	−0.00356 (4)
N1	0.0235 (9)	0.0255 (9)	0.0170 (8)	−0.0038 (7)	0.0025 (7)	−0.0049 (7)
N2	0.0405 (11)	0.0271 (10)	0.0236 (10)	−0.0120 (9)	0.0007 (8)	−0.0063 (8)
N3	0.0708 (17)	0.0278 (11)	0.0241 (11)	−0.0114 (11)	−0.0001 (11)	−0.0096 (9)
O1	0.0309 (8)	0.0277 (8)	0.0163 (7)	−0.0035 (7)	0.0063 (6)	−0.0041 (6)
O1W	0.0431 (10)	0.0254 (8)	0.0193 (8)	−0.0061 (7)	−0.0061 (7)	−0.0071 (6)
O2	0.131 (3)	0.0454 (13)	0.0338 (11)	−0.0453 (15)	0.0084 (13)	−0.0179 (10)
O2W	0.0260 (8)	0.0279 (9)	0.0506 (12)	−0.0042 (7)	0.0098 (8)	0.0028 (8)
O3	0.0825 (16)	0.0360 (11)	0.0251 (9)	−0.0260 (11)	0.0002 (10)	−0.0019 (8)
O3W	0.0295 (9)	0.0278 (9)	0.0340 (9)	0.0009 (7)	0.0082 (7)	0.0015 (7)
O4	0.0581 (12)	0.0327 (10)	0.0181 (8)	−0.0146 (9)	−0.0014 (8)	−0.0045 (7)
O4W	0.0374 (9)	0.0250 (8)	0.0223 (8)	−0.0126 (7)	−0.0011 (7)	−0.0011 (6)
O5	0.289 (6)	0.0440 (15)	0.0247 (12)	−0.051 (2)	−0.018 (2)	−0.0095 (10)
O5W	0.143 (3)	0.0332 (12)	0.0434 (14)	−0.0063 (15)	−0.0147 (16)	−0.0135 (10)
O6	0.196 (4)	0.0310 (13)	0.0439 (14)	−0.0246 (17)	0.0042 (19)	−0.0161 (11)
O6W	0.0596 (13)	0.0429 (11)	0.0366 (11)	−0.0140 (10)	−0.0045 (10)	−0.0163 (9)
O7	0.0230 (8)	0.0416 (10)	0.0379 (10)	−0.0121 (7)	0.0062 (7)	−0.0264 (8)
O7W	0.0364 (10)	0.0282 (9)	0.0418 (10)	−0.0110 (7)	−0.0046 (8)	−0.0035 (8)
O8	0.0240 (8)	0.0359 (9)	0.0300 (9)	−0.0120 (7)	0.0066 (7)	−0.0200 (7)
O8W	0.0771 (16)	0.0401 (12)	0.0403 (12)	−0.0189 (11)	−0.0021 (11)	−0.0123 (9)
O9	0.0309 (8)	0.0195 (7)	0.0222 (8)	−0.0056 (6)	−0.0070 (6)	−0.0022 (6)
O10	0.0488 (10)	0.0176 (8)	0.0240 (8)	−0.0041 (7)	−0.0123 (7)	−0.0049 (6)
C1	0.0215 (10)	0.0253 (11)	0.0215 (10)	−0.0038 (8)	0.0016 (8)	−0.0083 (8)
C2	0.0223 (10)	0.0236 (11)	0.0207 (10)	−0.0055 (8)	0.0008 (8)	−0.0061 (8)
C3	0.0250 (10)	0.0254 (11)	0.0198 (10)	−0.0041 (8)	−0.0006 (8)	−0.0067 (8)
C4	0.0333 (12)	0.0242 (11)	0.0218 (11)	−0.0055 (9)	0.0002 (9)	−0.0095 (9)
C5	0.0312 (11)	0.0216 (11)	0.0256 (11)	−0.0062 (9)	0.0028 (9)	−0.0071 (9)
C6	0.0191 (10)	0.0205 (10)	0.0202 (10)	−0.0034 (8)	0.0015 (8)	−0.0078 (8)
C7	0.0238 (10)	0.0197 (10)	0.0187 (10)	−0.0053 (8)	−0.0011 (8)	−0.0043 (8)

Geometric parameters (Å, º) top

Nd1—O1	2.5266 (16)	O4—C3	1.246 (3)
Nd1—O7	2.5124 (16)	O4W—H41	0.8391
Nd1—O8ⁱ	2.4972 (16)	O4W—H42	0.8323
Nd1—O9	2.5243 (16)	O5W—H51	0.8401
Nd1—O10ⁱⁱ	2.4897 (16)	O5W—H52	0.8205
Nd1—O1W	2.4798 (16)	O6W—H61	0.8420
Nd1—O2W	2.5080 (17)	O6W—H62	0.8503
Nd1—O3W	2.5241 (17)	O7—C6	1.255 (3)
Nd1—O4W	2.5153 (16)	O7W—H71	0.8363
N1—C5	1.346 (3)	O7W—H72	0.8351
N1—C1	1.350 (3)	O8—C6	1.251 (3)
N1—O1	1.364 (2)	O8W—H81	0.8498
N2—O2	1.223 (3)	O8W—H82	0.8376
N2—O3	1.222 (3)	O9—C7	1.250 (3)
N2—C2	1.459 (3)	O10—C7	1.258 (3)
N3—O5	1.189 (3)	C1—C2	1.373 (3)
N3—O6	1.210 (3)	C1—H1	0.9300
N3—C4	1.459 (3)	C2—C3	1.461 (3)
O1W—H11	0.8381	C3—C4	1.456 (3)
O1W—H12	0.8435	C4—C5	1.375 (3)
O2W—H21	0.8386	C5—H5	0.9300
O2W—H22	0.8392	C6—C6ⁱ	1.538 (4)
O3W—H31	0.8474	C7—C7ⁱⁱ	1.563 (4)
O3W—H32	0.8431

O1W—Nd1—O10ⁱⁱ	135.33 (5)	O6—N3—C4	119.1 (2)
O1W—Nd1—O8ⁱ	131.00 (6)	N1—O1—Nd1	119.90 (12)
O10ⁱⁱ—Nd1—O8ⁱ	70.29 (6)	Nd1—O1W—H11	120.2
O1W—Nd1—O2W	91.36 (6)	Nd1—O1W—H12	127.9
O10ⁱⁱ—Nd1—O2W	81.90 (6)	H11—O1W—H12	108.0
O8ⁱ—Nd1—O2W	137.49 (6)	Nd1—O2W—H21	125.7
O1W—Nd1—O7	148.48 (6)	Nd1—O2W—H22	125.1
O10ⁱⁱ—Nd1—O7	72.57 (6)	H21—O2W—H22	108.9
O8ⁱ—Nd1—O7	64.62 (5)	Nd1—O3W—H31	111.6
O2W—Nd1—O7	76.89 (6)	Nd1—O3W—H32	121.7
O1W—Nd1—O4W	73.70 (6)	H31—O3W—H32	108.4
O10ⁱⁱ—Nd1—O4W	139.35 (6)	Nd1—O4W—H41	126.0
O8ⁱ—Nd1—O4W	69.18 (6)	Nd1—O4W—H42	123.9
O2W—Nd1—O4W	132.51 (6)	H41—O4W—H42	108.6
O7—Nd1—O4W	92.70 (6)	H51—O5W—H52	114.0
O1W—Nd1—O9	71.57 (5)	H61—O6W—H62	108.1
O10ⁱⁱ—Nd1—O9	65.01 (5)	C6—O7—Nd1	120.14 (14)
O8ⁱ—Nd1—O9	122.97 (6)	H71—O7W—H72	110.0
O2W—Nd1—O9	67.67 (6)	C6—O8—Nd1ⁱ	121.03 (14)
O7—Nd1—O9	127.25 (6)	H81—O8W—H82	111.9
O4W—Nd1—O9	140.03 (6)	C7—O9—Nd1	119.52 (14)
O1W—Nd1—O3W	79.37 (6)	C7—O10—Nd1ⁱⁱ	121.18 (14)
O10ⁱⁱ—Nd1—O3W	134.04 (6)	N1—C1—C2	120.4 (2)
O8ⁱ—Nd1—O3W	112.90 (6)	N1—C1—H1	119.8
O2W—Nd1—O3W	65.61 (6)	C2—C1—H1	119.8
O7—Nd1—O3W	69.13 (6)	C1—C2—N2	114.8 (2)
O4W—Nd1—O3W	67.38 (6)	C1—C2—C3	123.9 (2)
O9—Nd1—O3W	123.39 (6)	N2—C2—C3	121.22 (19)
O1W—Nd1—O1	76.77 (6)	O4—C3—C4	124.5 (2)
O10ⁱⁱ—Nd1—O1	79.67 (6)	O4—C3—C2	125.6 (2)
O8ⁱ—Nd1—O1	67.82 (6)	C4—C3—C2	109.93 (19)
O2W—Nd1—O1	138.53 (6)	C5—C4—N3	115.0 (2)
O7—Nd1—O1	130.56 (5)	C5—C4—C3	124.1 (2)
O4W—Nd1—O1	82.50 (6)	N3—C4—C3	120.9 (2)
O9—Nd1—O1	70.89 (5)	N1—C5—C4	120.4 (2)
O3W—Nd1—O1	145.78 (5)	N1—C5—H5	119.8
C5—N1—C1	120.8 (2)	C4—C5—H5	119.8
C5—N1—O1	119.60 (19)	O8—C6—O7	125.9 (2)
C1—N1—O1	119.60 (18)	O8—C6—C6ⁱ	116.9 (2)
O2—N2—O3	122.3 (2)	O7—C6—C6ⁱ	117.2 (2)
O2—N2—C2	118.1 (2)	O9—C7—O10	126.3 (2)
O3—N2—C2	119.6 (2)	O9—C7—C7ⁱⁱ	117.4 (2)
O5—N3—O6	121.0 (3)	O10—C7—C7ⁱⁱ	116.2 (2)
O5—N3—C4	119.9 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O4ⁱⁱⁱ	0.84	1.99	2.809 (2)	166
O1w—H12···O5w	0.84	1.89	2.736 (3)	178
O2w—H21···O8^iv	0.84	2.06	2.890 (2)	174
O2w—H22···O7w	0.84	1.97	2.806 (3)	174
O3w—H31···O7^iv	0.85	2.07	2.908 (2)	170
O3w—H32···O8w^iv	0.84	2.03	2.841 (3)	161
O4w—H41···O4ⁱⁱⁱ	0.84	1.97	2.759 (2)	155
O4w—H42···O6w^v	0.83	2.02	2.851 (3)	177
O5w—H51···O6w	0.84	2.06	2.893 (3)	171
O5w—H52···O3ⁱⁱⁱ	0.82	2.43	2.956 (3)	123
O6w—H61···O10	0.84	2.09	2.915 (3)	168
O6w—H62···O8wⁱⁱ	0.85	2.13	2.942 (3)	160
O7w—H71···O1ⁱⁱ	0.84	1.93	2.766 (2)	172
O7w—H72···O9^vi	0.84	2.13	2.953 (2)	168
O8w—H81···O6ⁱⁱ	0.85	2.46	3.310 (4)	174
O8w—H82···O7w	0.84	2.02	2.816 (3)	160

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

Experimental details

Crystal data
Chemical formula	[Nd(C₅H₂N₃O₆)(C₂O₄)(H₂O)₄]·4H₂O
M_r	576.48
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.7695 (7), 9.9695 (11), 14.6269 (16)
α, β, γ (°)	73.719 (1), 88.137 (1), 76.693 (1)
V (Å³)	921.58 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.92
Crystal size (mm)	0.35 × 0.25 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffraractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.429, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	7952, 4147, 4005
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.050, 1.06
No. of reflections	4147
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.94

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Nd1—O1	2.5266 (16)	Nd1—O1W	2.4798 (16)
Nd1—O7	2.5124 (16)	Nd1—O2W	2.5080 (17)
Nd1—O8ⁱ	2.4972 (16)	Nd1—O3W	2.5241 (17)
Nd1—O9	2.5243 (16)	Nd1—O4W	2.5153 (16)
Nd1—O10ⁱⁱ	2.4897 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O4ⁱⁱⁱ	0.84	1.99	2.809 (2)	166
O1w—H12···O5w	0.84	1.89	2.736 (3)	178
O2w—H21···O8^iv	0.84	2.06	2.890 (2)	174
O2w—H22···O7w	0.84	1.97	2.806 (3)	174
O3w—H31···O7^iv	0.85	2.07	2.908 (2)	170
O3w—H32···O8w^iv	0.84	2.03	2.841 (3)	161
O4w—H41···O4ⁱⁱⁱ	0.84	1.97	2.759 (2)	155
O4w—H42···O6w^v	0.83	2.02	2.851 (3)	177
O5w—H51···O6w	0.84	2.06	2.893 (3)	171
O5w—H52···O3ⁱⁱⁱ	0.82	2.43	2.956 (3)	123
O6w—H61···O10	0.84	2.09	2.915 (3)	168
O6w—H62···O8wⁱⁱ	0.85	2.13	2.942 (3)	160
O7w—H71···O1ⁱⁱ	0.84	1.93	2.766 (2)	172
O7w—H72···O9^vi	0.84	2.13	2.953 (2)	168
O8w—H81···O6ⁱⁱ	0.85	2.46	3.310 (4)	174
O8w—H82···O7w	0.84	2.02	2.816 (3)	160

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

Acknowledgements

We thank Baoji University of Arts and Sciences (Key Research Project No. ZK08114) and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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Wang, J.-G., Zhou, Q.-P., Zhang, G.-F., Li, P., Chen, B.-H., Zhao, F.-Q., Li, J.-Z. & Fan, X.-Z. (2010). J. Coord. Chem. 63, 1379–1389. Web of Science CSD CrossRef CAS Google Scholar
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