Poly[[aqua­(μ2-oxalato)(μ2-2-oxido­pyridinium-3-carboxylato)dysprosium(III)] monohydrate]

Huang, C.-D.; Huang, J.-X.; Wu, Y.-Y.; Lian, Y.-Y.; Zeng, R.-H.

doi:10.1107/S1600536809000580

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages m177-m178

doi:10.1107/S1600536809000580

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Poly[[aqua(μ₂-oxalato)(μ₂-2-oxidopyridinium-3-carboxylato)dysprosium(III)] monohydrate]

Chun-De Huang,^a Jie-Xuan Huang,^a Yi-Yi Wu,^a Ying-Yang Lian ^a and Rong-Hua Zeng ^a,^b ^*

^aSchool of Chemistry and the Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and ^bSouth China Normal University, Key Laboratory of Technology on Electrochemical Energy Storage and Power Generation in Guangdong Universities, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: zrh321@yahoo.com.cn

(Received 20 December 2008; accepted 7 January 2009; online 10 January 2009)

In the title complex, {[Dy(C₆H₄NO₃)(C₂O₄)(H₂O)]·H₂O}_n, the Dy^III ion is coordinated by seven O atoms from two 2-oxidopyridinium-3-carboxylate ligands, two oxalate ligands and one water molecule, displaying a distorted bicapped trigonal-prismatic geometry. The carboxylate groups of the 2-oxidopyridinium-3-carboxylate and oxalate ligands link dysprosium metal centres, forming layers parallel to (100). These layers are further connected by intermolecular O—H⋯O hydrogen-bonding interactions involving the coordinated water molecules, forming a three-dimensional supramolecular network. The uncoordinated water molecule is involved in N—H⋯O and O—H⋯O hydrogen-bonding interactions within the layer.

Related literature

For background to the molecular self-assembly of supramolecular architectures, see: Moulton & Zaworotko (2001 ); Zeng et al. (2007 ).

Experimental

Crystal data

[Dy(C₆H₄NO₃)(C₂O₄)(H₂O)]·H₂O
M_r = 424.65
Triclinic, $[P \overline 1]$
a = 6.5359 (15) Å
b = 9.561 (2) Å
c = 9.734 (2) Å
α = 71.906 (2)°
β = 78.800 (3)°
γ = 80.305 (2)°
V = 563.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 6.68 mm⁻¹
T = 296 (2) K
0.17 × 0.16 × 0.14 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (APEX2; Bruker, 2004 ) T_min = 0.397, T_max = 0.455 (expected range = 0.342–0.393)
2926 measured reflections
2003 independent reflections
1888 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.077
S = 1.09
2003 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 2.29 e Å⁻³
Δρ_min = −1.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2W	0.86	1.99	2.785 (9)	154
O1W—H1W⋯O2ⁱ	0.85	1.94	2.732 (7)	155
O1W—H2W⋯O4ⁱⁱ	0.85	2.07	2.751 (7)	137
O2W—H4W⋯O1ⁱⁱⁱ	0.85	2.26	3.080 (8)	163
O2W—H4W⋯O6ⁱⁱⁱ	0.85	2.36	2.878 (8)	120
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) x+1, y, z; (iii) x, y, z-1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000580/dn2421sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000580/dn2421Isup2.hkl

checkCIF report

Comment top

Molecular self-assembly of supramolecular architectures has received much attention during recent decades (Zeng et al., 2007; Moulton & Zaworotko, 2001). The structures and properties of such systems depend on the coordination and geometric preferences of both the central metal ions and the bridging building blocks, as well as the influence of weaker non-covalent interactions, such as hydrogen bonds and π-π stacking interactions. Recently, we obtained the title coordination polymer, which was synthesized under hydrothermal conditions.

In the structure of the title compound, each Dy^III centre is in a bicapped trigonal prismatic geometry, defined by seven oxygen atoms from two 2-oxidopyridinium-3-carboxylate ligands, one oxalate ligand, and one water molecule Fig. 1. The Dy^III ions are linked by 2-oxidopyridinium-3-carboxylate ligands and oxalate ligands to form a layer in the bc plane, and the adjacent Dy···Dy separations are 5.858 (4), 6.186 (5) and 6.239 Å, respectively. The layers are further connected by ιntermolecular O—H···O hydrogen bonding interactions inolving the coordinated water molecules to form a three-dimensional supramolecular network (Table 1, Fig. 2). Within each layer, free water molecules further link the complexes through N-H···O and O-H···O bonding interactions (Table 1).

Related literature top

For background to the molecular self-assembly of supramolecular architectures, see: Moulton & Zaworotko (2001); Zeng et al. (2007).

Experimental top

A mixture of Dy₂O₃ (0.375 g; 1 mmol), 2-oxynicotinic acid (0.127 g; 1 mmol), oxalic acid (0.09 g; 1 mmol), water (10 ml) in the presence of HNO₃ (0.024 g; 0.385 mmol) was stirred vigorously for 20 min and then sealed in a Teflon-lined stainless-steel autoclave (20 ml, capacity). The autoclave was heated and maintained at 446 K for 2 days, and then cooled to room temperature at 5 K h^-1 and obtained the colorless block crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003; software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure showing the atomic-numbering scheme. Displacement ellipsoids drawn at the 30% probability level. Symmetry codes: (i)1 - x, 1 - y, 2 - z; (ii)1 - x, 2 - y, 1 - z; (iii)1 - x, 2 - y, 2 - z.
	Fig. 2. A view of the three-dimensional supramolecular network. Hydrogen bonds are shown as dashed lines.

Poly[[aqua(µ₂-oxalato)(µ₂-2-oxidopyridinium-3- carboxylato)dysprosium(III)] monohydrate] top

Crystal data top

[Dy(C₆H₄NO₃)(C₂O₄)(H₂O)]·H₂O	Z = 2
M_r = 424.65	F(000) = 402
Triclinic, P1	D_x = 2.503 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5359 (15) Å	Cell parameters from 6377 reflections
b = 9.561 (2) Å	θ = 1.7–28.0°
c = 9.734 (2) Å	µ = 6.68 mm⁻¹
α = 71.906 (2)°	T = 296 K
β = 78.800 (3)°	Block, colourless
γ = 80.305 (2)°	0.17 × 0.16 × 0.14 mm
V = 563.4 (2) Å³

Data collection top

Bruker APEXII area-detector diffractometer	2003 independent reflections
Radiation source: fine-focus sealed tube	1888 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.2°
Absorption correction: multi-scan (APEX2; Bruker, 2004)	h = −7→7
T_min = 0.397, T_max = 0.455	k = −11→9
2926 measured reflections	l = −11→7

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0379P)² + 2.6561P] where P = (F_o² + 2F_c²)/3
2003 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 2.29 e Å⁻³
0 restraints	Δρ_min = −1.55 e Å⁻³

Crystal data top

[Dy(C₆H₄NO₃)(C₂O₄)(H₂O)]·H₂O	γ = 80.305 (2)°
M_r = 424.65	V = 563.4 (2) Å³
Triclinic, P1	Z = 2
a = 6.5359 (15) Å	Mo Kα radiation
b = 9.561 (2) Å	µ = 6.68 mm⁻¹
c = 9.734 (2) Å	T = 296 K
α = 71.906 (2)°	0.17 × 0.16 × 0.14 mm
β = 78.800 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	2003 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2004)	1888 reflections with I > 2σ(I)
T_min = 0.397, T_max = 0.455	R_int = 0.021
2926 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.09	Δρ_max = 2.29 e Å⁻³
2003 reflections	Δρ_min = −1.55 e Å⁻³
172 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Dy1	0.59123 (5)	0.79001 (3)	0.80042 (3)	0.01511 (12)
O4	0.3353 (7)	0.8866 (5)	0.6354 (5)	0.0200 (10)
O1	0.7142 (8)	0.5573 (5)	0.9516 (5)	0.0228 (10)
O7	0.5714 (9)	0.9762 (6)	1.1684 (5)	0.0332 (13)
C6	0.7318 (12)	0.4932 (8)	0.6786 (8)	0.0255 (15)
O3	0.6553 (9)	0.6282 (5)	0.6621 (5)	0.0276 (11)
C8	0.5595 (11)	0.9416 (7)	1.0579 (7)	0.0205 (14)
O6	0.6333 (8)	0.8228 (5)	1.0278 (5)	0.0278 (11)
C7	0.3857 (10)	0.9806 (7)	0.5168 (7)	0.0162 (13)
O5	0.2701 (8)	1.0470 (5)	0.4234 (5)	0.0243 (11)
C1	0.7310 (10)	0.4252 (8)	0.9513 (7)	0.0204 (14)
N1	0.7737 (11)	0.4446 (7)	0.5575 (7)	0.0350 (15)
H1	0.7413	0.5052	0.4768	0.042*
C2	0.7787 (11)	0.3863 (7)	0.8109 (7)	0.0222 (14)
C3	0.8671 (14)	0.2456 (9)	0.8087 (9)	0.0353 (18)
H3	0.8970	0.1760	0.8954	0.042*
C5	0.8633 (15)	0.3065 (10)	0.5567 (10)	0.044 (2)
H5	0.8909	0.2816	0.4693	0.053*
C4	0.9127 (16)	0.2052 (10)	0.6788 (10)	0.051 (3)
H4	0.9756	0.1107	0.6775	0.061*
O2	0.7138 (8)	0.3183 (5)	1.0690 (5)	0.0232 (10)
O1W	0.9535 (9)	0.7979 (7)	0.7825 (6)	0.0398 (14)
H1W	1.0327	0.7410	0.8417	0.060*
H2W	1.0234	0.8615	0.7177	0.060*
O2W	0.7275 (12)	0.5642 (8)	0.2640 (7)	0.0591 (19)
H3W	0.6854	0.6442	0.2877	0.089*
H4W	0.7313	0.5812	0.1725	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Dy1	0.01446 (19)	0.01602 (18)	0.01286 (17)	−0.00079 (12)	−0.00214 (11)	−0.00175 (12)
O4	0.018 (3)	0.023 (2)	0.015 (2)	−0.007 (2)	−0.0030 (18)	0.0031 (18)
O1	0.029 (3)	0.020 (2)	0.017 (2)	−0.001 (2)	−0.0044 (19)	−0.0022 (19)
O7	0.046 (4)	0.029 (3)	0.027 (3)	0.009 (2)	−0.018 (2)	−0.011 (2)
C6	0.027 (4)	0.026 (4)	0.024 (4)	−0.006 (3)	0.000 (3)	−0.009 (3)
O3	0.038 (3)	0.025 (3)	0.019 (2)	0.003 (2)	−0.007 (2)	−0.008 (2)
C8	0.018 (4)	0.019 (3)	0.022 (3)	0.000 (3)	−0.002 (3)	−0.004 (3)
O6	0.035 (3)	0.023 (3)	0.026 (3)	0.008 (2)	−0.013 (2)	−0.009 (2)
C7	0.012 (4)	0.016 (3)	0.018 (3)	0.002 (3)	0.000 (2)	−0.004 (3)
O5	0.019 (3)	0.027 (3)	0.021 (2)	−0.006 (2)	−0.0065 (19)	0.005 (2)
C1	0.008 (3)	0.027 (4)	0.022 (3)	−0.006 (3)	−0.001 (2)	0.000 (3)
N1	0.041 (4)	0.037 (4)	0.028 (3)	−0.004 (3)	0.001 (3)	−0.015 (3)
C2	0.016 (4)	0.022 (3)	0.027 (4)	−0.003 (3)	0.001 (3)	−0.007 (3)
C3	0.036 (5)	0.029 (4)	0.038 (4)	−0.006 (4)	0.003 (4)	−0.009 (3)
C5	0.048 (6)	0.049 (5)	0.041 (5)	−0.006 (4)	0.006 (4)	−0.029 (4)
C4	0.063 (7)	0.034 (5)	0.053 (6)	−0.001 (5)	0.009 (5)	−0.021 (4)
O2	0.019 (3)	0.021 (2)	0.022 (2)	−0.001 (2)	−0.0043 (19)	0.0049 (19)
O1W	0.022 (3)	0.054 (4)	0.029 (3)	−0.010 (3)	−0.009 (2)	0.015 (3)
O2W	0.067 (5)	0.070 (5)	0.039 (4)	−0.019 (4)	−0.015 (3)	−0.004 (3)

Geometric parameters (Å, º) top

Dy1—O3	2.289 (5)	C7—O5	1.244 (8)
Dy1—O1W	2.352 (5)	C7—C7ⁱⁱ	1.549 (12)
Dy1—O2ⁱ	2.357 (5)	C1—O2	1.277 (8)
Dy1—O1	2.364 (4)	C1—C2	1.488 (9)
Dy1—O5ⁱⁱ	2.366 (4)	N1—C5	1.353 (11)
Dy1—O7ⁱⁱⁱ	2.391 (5)	N1—H1	0.8600
Dy1—O6	2.402 (5)	C2—C3	1.377 (11)
Dy1—O4	2.415 (4)	C3—C4	1.398 (12)
O4—C7	1.247 (8)	C3—H3	0.9300
O1—C1	1.250 (8)	C5—C4	1.336 (13)
O7—C8	1.239 (8)	C5—H5	0.9300
C6—O3	1.275 (9)	C4—H4	0.9300
C6—N1	1.361 (9)	O1W—H1W	0.8500
C6—C2	1.424 (10)	O1W—H2W	0.8490
C8—O6	1.255 (8)	O2W—H3W	0.8534
C8—C8ⁱⁱⁱ	1.547 (13)	O2W—H4W	0.8503

O3—Dy1—O1W	90.9 (2)	N1—C6—C2	115.8 (7)
O3—Dy1—O2ⁱ	90.55 (18)	C6—O3—Dy1	136.4 (4)
O1W—Dy1—O2ⁱ	148.35 (17)	O7—C8—O6	127.9 (6)
O3—Dy1—O1	73.20 (16)	O7—C8—C8ⁱⁱⁱ	116.5 (7)
O1W—Dy1—O1	75.35 (18)	O6—C8—C8ⁱⁱⁱ	115.6 (7)
O2ⁱ—Dy1—O1	74.84 (16)	C8—O6—Dy1	120.2 (4)
O3—Dy1—O5ⁱⁱ	81.96 (17)	O5—C7—O4	126.4 (6)
O1W—Dy1—O5ⁱⁱ	67.74 (17)	O5—C7—C7ⁱⁱ	116.8 (7)
O2ⁱ—Dy1—O5ⁱⁱ	143.60 (16)	O4—C7—C7ⁱⁱ	116.8 (7)
O1—Dy1—O5ⁱⁱ	134.77 (17)	C7—O5—Dy1ⁱⁱ	120.1 (4)
O3—Dy1—O7ⁱⁱⁱ	148.30 (17)	O1—C1—O2	122.5 (6)
O1W—Dy1—O7ⁱⁱⁱ	105.1 (2)	O1—C1—C2	120.4 (6)
O2ⁱ—Dy1—O7ⁱⁱⁱ	89.70 (19)	O2—C1—C2	117.1 (6)
O1—Dy1—O7ⁱⁱⁱ	136.90 (16)	C5—N1—C6	123.9 (7)
O5ⁱⁱ—Dy1—O7ⁱⁱⁱ	79.21 (18)	C5—N1—H1	118.0
O3—Dy1—O6	144.68 (17)	C6—N1—H1	118.0
O1W—Dy1—O6	75.02 (19)	C3—C2—C6	119.6 (7)
O2ⁱ—Dy1—O6	85.84 (17)	C3—C2—C1	119.9 (7)
O1—Dy1—O6	71.95 (16)	C6—C2—C1	120.5 (6)
O5ⁱⁱ—Dy1—O6	119.90 (17)	C2—C3—C4	121.4 (8)
O7ⁱⁱⁱ—Dy1—O6	66.91 (16)	C2—C3—H3	119.3
O3—Dy1—O4	77.17 (17)	C4—C3—H3	119.3
O1W—Dy1—O4	135.23 (16)	C4—C5—N1	121.4 (8)
O2ⁱ—Dy1—O4	75.68 (15)	C4—C5—H5	119.3
O1—Dy1—O4	137.50 (15)	N1—C5—H5	119.3
O5ⁱⁱ—Dy1—O4	67.92 (15)	C5—C4—C3	117.9 (8)
O7ⁱⁱⁱ—Dy1—O4	72.20 (16)	C5—C4—H4	121.0
O6—Dy1—O4	134.95 (16)	C3—C4—H4	121.0
C7—O4—Dy1	118.2 (4)	C1—O2—Dy1ⁱ	128.1 (4)
C1—O1—Dy1	136.4 (4)	Dy1—O1W—H1W	125.7
C8—O7—Dy1ⁱⁱⁱ	120.8 (4)	Dy1—O1W—H2W	124.6
O3—C6—N1	117.2 (6)	H1W—O1W—H2W	109.7
O3—C6—C2	127.0 (6)	H3W—O2W—H4W	109.6

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2W	0.86	1.99	2.785 (9)	154
O1W—H1W···O2^iv	0.85	1.94	2.732 (7)	155
O1W—H2W···O4^v	0.85	2.07	2.751 (7)	137
O2W—H4W···O1^vi	0.85	2.26	3.080 (8)	163
O2W—H4W···O6^vi	0.85	2.36	2.878 (8)	120

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

Experimental details

Crystal data
Chemical formula	[Dy(C₆H₄NO₃)(C₂O₄)(H₂O)]·H₂O
M_r	424.65
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.5359 (15), 9.561 (2), 9.734 (2)
α, β, γ (°)	71.906 (2), 78.800 (3), 80.305 (2)
V (Å³)	563.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.68
Crystal size (mm)	0.17 × 0.16 × 0.14

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (APEX2; Bruker, 2004)
T_min, T_max	0.397, 0.455
No. of measured, independent and observed [I > 2σ(I)] reflections	2926, 2003, 1888
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.077, 1.09
No. of reflections	2003
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.29, −1.55

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2W	0.86	1.99	2.785 (9)	153.9
O1W—H1W···O2ⁱ	0.85	1.94	2.732 (7)	154.8
O1W—H2W···O4ⁱⁱ	0.85	2.07	2.751 (7)	137.4
O2W—H4W···O1ⁱⁱⁱ	0.85	2.26	3.080 (8)	162.9
O2W—H4W···O6ⁱⁱⁱ	0.85	2.36	2.878 (8)	119.9

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

Acknowledgements

The authors acknowledge South China Normal University for supporting this work.

References

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