Poly[μ-5-ammonio­isophthalato-aqua-μ-oxalato-dysprosium(III)]

Yan, L.-S.; Huang, D.-H.; Liu, C.-B.

doi:10.1107/S1600536809019199

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m750

doi:10.1107/S1600536809019199

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Poly[μ-5-ammonioisophthalato-aqua-μ-oxalato-dysprosium(III)]

Liu-Shui Yan,^a De-He Huang ^a and Chong-Bo Liu ^a ^*

^aSchool of Environment and Chemical Engineering, Nanchang Hangkong University, Nanchang 330063, People's Republic of China
^*Correspondence e-mail: cbliu2002@163.com

(Received 1 May 2009; accepted 20 May 2009; online 6 June 2009)

The title complex, [Dy(C₈H₆NO₄)(C₂O₄)(H₂O)]_n, is a dysprosium coordination polymer with mixed anions and was obtained under hydrothermal conditions. In the structure, the oxalate and 5-aminoisophthalate ligands link the dysprosium ions, building up a two-dimensional metal–organic framework parallel to the (10 $[\overline{1}]$ ) plane. These sheets are further connected through O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional supramolecular structure.

Related literature

For related structures, see: Chen et al. (2005 ); for isotypic structures, see: Liu et al. (2008 ).

Experimental

Crystal data

[Dy(C₈H₆NO₄)(C₂O₄)(H₂O)]
M_r = 448.67
Monoclinic, C 2/c
a = 19.951 (4) Å
b = 9.3967 (18) Å
c = 13.598 (3) Å
β = 118.478 (2)°
V = 2240.8 (8) Å³
Z = 8
Mo Kα radiation
μ = 6.72 mm⁻¹
T = 296 K
0.12 × 0.11 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.499, T_max = 0.568 (expected range = 0.449–0.511)
8393 measured reflections
2089 independent reflections
1901 reflections with I > 2σ(I)
R_int = 0.109

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.063
S = 1.08
2089 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 1.29 e Å⁻³
Δρ_min = −1.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H2W⋯O3ⁱ	0.83	2.32	2.858 (4)	123
O9—H1W⋯O1ⁱⁱ	0.83	1.97	2.790 (4)	168
N1—H1B⋯O6ⁱⁱ	0.89	2.63	3.379 (5)	142
N1—H1A⋯O8ⁱⁱ	0.89	2.39	2.824 (5)	111
N1—H1A⋯O5ⁱⁱⁱ	0.89	1.99	2.840 (5)	160
N1—H1C⋯O7^iv	0.89	1.92	2.796 (6)	169
C2—H2⋯O9ⁱⁱ	0.93	2.55	3.421 (5)	157
C4—H4⋯O5^iv	0.93	2.53	3.169 (6)	126
Symmetry codes: (i) $[-x+1, y-1, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019199/dn2450sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019199/dn2450Isup2.hkl

checkCIF report

Comment top

In recent years, the chemistry of supramolecular coordination polymers with mixed carboxylates has received much attention, and our group (Liu et al., 2008) described the structure of europium and holmium coordination polymers with oxalate and 5-aminoisophthalate, the present dysprosium complex is similar to the europium and holmium complex.

In the title complex, the dysprosium ion is coordinated to nine oxygen atoms, among which one oxygen atom from one water molecule, four oxygen atoms from three HAPA ions, and the other four oxygen atoms from two oxalate ions. The two carboxylate groups of H₂APA ligands are both completely deprotonated and exhibit chelating and bridging bidentate coordination modes respectively (Fig. 1). The amino group exist as –NH₃⁺ (Chen et al., 2005) . So, each HAPA ligand links three dysprosium atoms with Dy···Dy distances of 9.786, 9.397 and 5.419 Å, each oxalate ligand chelates two Dy(III) ions with a Dy···Dy distance of 6.259 Å, as shown in Fig. 1. The carboxylate groups of HAPA ligands link the Dy³⁺ ions to the dimeric units, which are further joined to a 2-D metal-organic framework containing regular parallelograms via HAPA ligands and OX ligands along c axis, as shown in Fig. 2. O—H···O and N—H···O hydrogen bonds link these layers to form a 3-D supramolecular structure.

The structure of the title complex is similar to that of other lanthanide (europium and holmium) coordination polymers with HAPA and oxalate ligands, and the mean Dy—O distance in the title complex of 2.430Å is between that of Eu—O (2.4728 Å) and Ho—O (2.4251 Å).

Related literature top

For related structures, see: Chen et al. (2005); Liu et al. (2008).

Experimental top

DyCl₃.6H₂O (0.038 g, 0.1 mmol), 0.018 g 5-aminoisophthalic acid (0.1 mmol), 0.013 g oxalic acid (0.1 mmol), 10 ml deionized water and 0.1 mmol 0.65 M NaOH aqueous solution were sealed in a 25 ml Teflon-lined stainless reactor and heated at 393 K for 72 h under autogeneous pressure, then cooled to room temperature. Colorless crystals of 1 were obtained. Anal. Calcd. for C10H8DyNO9 (448.67): C 26.75, H 1.78, N 3.12; found C 26.46, H 2.16, N 3.43.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Coordination environment of the Dy(III) ion with the atom labeling scheme. Ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+2, -z+2; (iii) -x+1/2, y-1/2, -z+3/2; (iv) x, y+1, z; ]
	Fig. 2. Packing view showing the 2-D metal organic framework. H atoms have been omitted for clarity.

poly[µ-5-ammonioisophthalato-aqua-µ-oxalato-dysprosium(III)] top

Crystal data top

[Dy(C₈H₆NO₄)(C₂O₄)(H₂O)]	F(000) = 1704
M_r = 448.67	D_x = 2.660 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5702 reflections
a = 19.951 (4) Å	θ = 2.5–28.2°
b = 9.3967 (18) Å	µ = 6.72 mm⁻¹
c = 13.598 (3) Å	T = 296 K
β = 118.478 (2)°	Block, colourless
V = 2240.8 (8) Å³	0.12 × 0.11 × 0.10 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	2089 independent reflections
Radiation source: fine-focus sealed tube	1901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.109
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −24→24
T_min = 0.499, T_max = 0.568	k = −11→11
8393 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0094P)² + 0.8384P] where P = (F_o² + 2F_c²)/3
2089 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 1.29 e Å⁻³
0 restraints	Δρ_min = −1.56 e Å⁻³

Crystal data top

[Dy(C₈H₆NO₄)(C₂O₄)(H₂O)]	V = 2240.8 (8) Å³
M_r = 448.67	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 19.951 (4) Å	µ = 6.72 mm⁻¹
b = 9.3967 (18) Å	T = 296 K
c = 13.598 (3) Å	0.12 × 0.11 × 0.10 mm
β = 118.478 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2089 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	1901 reflections with I > 2σ(I)
T_min = 0.499, T_max = 0.568	R_int = 0.109
8393 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.08	Δρ_max = 1.29 e Å⁻³
2089 reflections	Δρ_min = −1.56 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	0.5101 (3)	0.9321 (4)	0.8770 (5)	0.0176 (11)
C2	0.5866 (3)	0.9047 (4)	0.9083 (4)	0.0168 (10)
H2	0.6038	0.8119	0.9121	0.020*
C3	0.6362 (2)	1.0187 (5)	0.9335 (4)	0.0161 (10)
C4	0.6139 (3)	1.1553 (5)	0.9341 (4)	0.0198 (10)
H4	0.6489	1.2293	0.9532	0.024*
C5	0.5376 (2)	1.1837 (4)	0.9057 (4)	0.0159 (9)
C6	0.4854 (3)	1.0707 (4)	0.8733 (4)	0.0154 (10)
H6	0.4340	1.0889	0.8492	0.018*
C7	0.4569 (3)	0.8075 (5)	0.8484 (4)	0.0170 (10)
C8	0.5160 (3)	1.3320 (4)	0.9189 (4)	0.0171 (10)
C9	0.2265 (2)	0.7844 (4)	0.6760 (4)	0.0143 (9)
C10	0.2352 (2)	0.7786 (4)	0.7938 (4)	0.0142 (9)
Dy1	0.367163 (11)	0.562032 (19)	0.814740 (18)	0.01134 (10)
N1	0.7158 (2)	0.9903 (4)	0.9663 (4)	0.0198 (9)
H1A	0.7278	1.0315	0.9178	0.030*
H1B	0.7231	0.8968	0.9667	0.030*
H1C	0.7452	1.0254	1.0344	0.030*
O1	0.48363 (19)	0.6844 (3)	0.8541 (3)	0.0234 (8)
O2	0.38806 (19)	0.8260 (3)	0.8218 (3)	0.0238 (8)
O3	0.56915 (19)	1.4094 (3)	0.9915 (3)	0.0183 (7)
O4	0.44868 (18)	1.3699 (3)	0.8570 (3)	0.0218 (8)
O5	0.26983 (18)	0.6716 (3)	0.8522 (3)	0.0200 (7)
O6	0.26011 (19)	0.6905 (3)	0.6506 (3)	0.0256 (8)
O7	0.20849 (18)	0.8801 (3)	0.8235 (3)	0.0193 (7)
O8	0.18745 (18)	0.8842 (3)	0.6150 (3)	0.0199 (7)
O9	0.3929 (2)	0.5616 (3)	0.6572 (3)	0.0240 (8)
H1W	0.4336	0.5912	0.6625	0.036*
H2W	0.3713	0.5057	0.6041	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.019 (3)	0.018 (2)	0.017 (3)	−0.0046 (17)	0.010 (2)	−0.0018 (18)
C2	0.020 (3)	0.0092 (18)	0.021 (3)	0.0011 (17)	0.009 (2)	−0.0042 (19)
C3	0.012 (2)	0.020 (2)	0.015 (3)	0.0006 (19)	0.005 (2)	0.000 (2)
C4	0.019 (2)	0.019 (2)	0.023 (3)	−0.0026 (19)	0.010 (2)	−0.001 (2)
C5	0.014 (2)	0.016 (2)	0.014 (2)	−0.0007 (18)	0.0033 (19)	−0.0011 (19)
C6	0.014 (2)	0.017 (2)	0.015 (3)	−0.0021 (17)	0.007 (2)	−0.0006 (18)
C7	0.021 (2)	0.017 (2)	0.014 (3)	−0.0022 (19)	0.009 (2)	−0.0014 (19)
C8	0.018 (2)	0.017 (2)	0.017 (3)	−0.0025 (19)	0.009 (2)	0.002 (2)
C9	0.011 (2)	0.013 (2)	0.017 (3)	−0.0031 (16)	0.005 (2)	−0.0055 (18)
C10	0.010 (2)	0.015 (2)	0.017 (3)	−0.0020 (16)	0.006 (2)	0.0007 (18)
Dy1	0.00982 (14)	0.00969 (13)	0.01363 (16)	−0.00032 (7)	0.00488 (12)	−0.00066 (7)
N1	0.017 (2)	0.0198 (19)	0.024 (3)	0.0041 (16)	0.011 (2)	0.0027 (18)
O1	0.0235 (17)	0.0157 (15)	0.033 (2)	−0.0055 (14)	0.0152 (17)	−0.0056 (16)
O2	0.0188 (16)	0.0216 (16)	0.031 (2)	−0.0024 (14)	0.0118 (15)	−0.0007 (15)
O3	0.0214 (18)	0.0152 (14)	0.016 (2)	−0.0012 (13)	0.0072 (16)	−0.0040 (14)
O4	0.0130 (17)	0.0173 (15)	0.027 (2)	0.0061 (13)	0.0032 (16)	−0.0008 (15)
O5	0.0158 (16)	0.0177 (15)	0.029 (2)	0.0055 (13)	0.0123 (15)	0.0086 (15)
O6	0.0208 (17)	0.0264 (17)	0.023 (2)	0.0051 (15)	0.0056 (16)	−0.0064 (16)
O7	0.0180 (17)	0.0205 (16)	0.017 (2)	0.0048 (13)	0.0069 (15)	−0.0020 (14)
O8	0.0205 (17)	0.0194 (16)	0.021 (2)	0.0051 (13)	0.0111 (16)	0.0044 (15)
O9	0.025 (2)	0.0261 (18)	0.029 (2)	−0.0066 (13)	0.0191 (19)	−0.0063 (14)

Geometric parameters (Å, º) top

C1—C6	1.385 (6)	C9—C10	1.528 (6)
C1—C2	1.399 (7)	C10—O7	1.250 (5)
C1—C7	1.502 (6)	C10—O5	1.263 (5)
C2—C3	1.386 (6)	Dy1—O4ⁱ	2.312 (3)
C2—H2	0.9300	Dy1—O3ⁱⁱ	2.332 (4)
C3—C4	1.359 (6)	Dy1—O1	2.413 (3)
C3—N1	1.455 (5)	Dy1—O8ⁱⁱⁱ	2.426 (3)
C4—C5	1.408 (6)	Dy1—O9	2.429 (3)
C4—H4	0.9300	Dy1—O7ⁱⁱⁱ	2.455 (3)
C5—C6	1.403 (6)	Dy1—O5	2.456 (3)
C5—C8	1.494 (6)	Dy1—O2	2.509 (3)
C6—H6	0.9300	Dy1—O6	2.541 (4)
C7—O2	1.254 (5)	N1—H1A	0.8900
C7—O1	1.260 (5)	N1—H1B	0.8900
C8—O4	1.249 (6)	N1—H1C	0.8900
C8—O3	1.277 (6)	O9—H1W	0.8287
C9—O8	1.248 (5)	O9—H2W	0.8292
C9—O6	1.252 (5)

C6—C1—C2	120.2 (4)	O1—Dy1—O7ⁱⁱⁱ	132.63 (11)
C6—C1—C7	121.9 (4)	O8ⁱⁱⁱ—Dy1—O7ⁱⁱⁱ	66.07 (11)
C2—C1—C7	118.0 (4)	O9—Dy1—O7ⁱⁱⁱ	68.59 (11)
C3—C2—C1	118.7 (4)	O4ⁱ—Dy1—O5	143.90 (11)
C3—C2—H2	120.7	O3ⁱⁱ—Dy1—O5	77.07 (11)
C1—C2—H2	120.7	O1—Dy1—O5	121.80 (11)
C4—C3—C2	122.3 (4)	O8ⁱⁱⁱ—Dy1—O5	70.08 (10)
C4—C3—N1	118.9 (4)	O9—Dy1—O5	134.73 (12)
C2—C3—N1	118.7 (4)	O7ⁱⁱⁱ—Dy1—O5	101.09 (11)
C3—C4—C5	119.4 (4)	O4ⁱ—Dy1—O2	132.70 (11)
C3—C4—H4	120.3	O3ⁱⁱ—Dy1—O2	81.48 (11)
C5—C4—H4	120.3	O1—Dy1—O2	52.80 (10)
C6—C5—C4	119.1 (4)	O8ⁱⁱⁱ—Dy1—O2	139.77 (10)
C6—C5—C8	122.0 (4)	O9—Dy1—O2	86.23 (10)
C4—C5—C8	118.7 (4)	O7ⁱⁱⁱ—Dy1—O2	138.39 (11)
C1—C6—C5	120.1 (4)	O5—Dy1—O2	73.20 (10)
C1—C6—H6	119.9	O4ⁱ—Dy1—O6	141.86 (12)
C5—C6—H6	119.9	O3ⁱⁱ—Dy1—O6	135.64 (11)
O2—C7—O1	121.2 (4)	O1—Dy1—O6	106.59 (11)
O2—C7—C1	120.5 (4)	O8ⁱⁱⁱ—Dy1—O6	109.04 (11)
O1—C7—C1	118.3 (4)	O9—Dy1—O6	70.64 (11)
O4—C8—O3	126.0 (4)	O7ⁱⁱⁱ—Dy1—O6	72.89 (10)
O4—C8—C5	117.6 (4)	O5—Dy1—O6	64.31 (11)
O3—C8—C5	116.3 (4)	O2—Dy1—O6	67.58 (11)
O8—C9—O6	126.4 (5)	C3—N1—H1A	109.5
O8—C9—C10	116.5 (4)	C3—N1—H1B	109.5
O6—C9—C10	117.2 (4)	H1A—N1—H1B	109.5
O7—C10—O5	126.4 (4)	C3—N1—H1C	109.5
O7—C10—C9	117.3 (4)	H1A—N1—H1C	109.5
O5—C10—C9	116.2 (4)	H1B—N1—H1C	109.5
O4ⁱ—Dy1—O3ⁱⁱ	82.50 (12)	C7—O1—Dy1	95.1 (3)
O4ⁱ—Dy1—O1	80.12 (11)	C7—O2—Dy1	90.7 (3)
O3ⁱⁱ—Dy1—O1	75.29 (12)	C8—O3—Dy1ⁱⁱ	138.0 (3)
O4ⁱ—Dy1—O8ⁱⁱⁱ	76.05 (11)	C8—O4—Dy1^iv	142.5 (3)
O3ⁱⁱ—Dy1—O8ⁱⁱⁱ	74.89 (11)	C10—O5—Dy1	116.9 (3)
O1—Dy1—O8ⁱⁱⁱ	143.78 (12)	C9—O6—Dy1	115.4 (3)
O4ⁱ—Dy1—O9	78.37 (12)	C10—O7—Dy1^v	119.0 (3)
O3ⁱⁱ—Dy1—O9	140.02 (12)	C9—O8—Dy1^v	120.8 (3)
O1—Dy1—O9	67.07 (12)	Dy1—O9—H1W	122.3
O8ⁱⁱⁱ—Dy1—O9	132.03 (11)	Dy1—O9—H2W	121.9
O4ⁱ—Dy1—O7ⁱⁱⁱ	75.48 (11)	H1W—O9—H2W	111.7
O3ⁱⁱ—Dy1—O7ⁱⁱⁱ	138.61 (10)

C6—C1—C2—C3	−1.0 (8)	O4ⁱ—Dy1—O2—C7	4.5 (3)
C7—C1—C2—C3	179.1 (5)	O3ⁱⁱ—Dy1—O2—C7	76.0 (3)
C1—C2—C3—C4	3.3 (7)	O1—Dy1—O2—C7	−2.0 (3)
C1—C2—C3—N1	179.9 (4)	O8ⁱⁱⁱ—Dy1—O2—C7	130.2 (3)
C2—C3—C4—C5	−1.6 (8)	O9—Dy1—O2—C7	−65.8 (3)
N1—C3—C4—C5	−178.2 (4)	O7ⁱⁱⁱ—Dy1—O2—C7	−117.2 (3)
C3—C4—C5—C6	−2.3 (8)	O5—Dy1—O2—C7	155.0 (3)
C3—C4—C5—C8	173.4 (4)	O6—Dy1—O2—C7	−136.4 (3)
C2—C1—C6—C5	−2.9 (8)	O4—C8—O3—Dy1ⁱⁱ	103.1 (5)
C7—C1—C6—C5	177.0 (5)	C5—C8—O3—Dy1ⁱⁱ	−78.5 (5)
C4—C5—C6—C1	4.6 (8)	O3—C8—O4—Dy1^iv	−0.3 (8)
C8—C5—C6—C1	−171.0 (5)	C5—C8—O4—Dy1^iv	−178.6 (3)
C6—C1—C7—O2	−1.2 (8)	O7—C10—O5—Dy1	−149.7 (4)
C2—C1—C7—O2	178.7 (5)	C9—C10—O5—Dy1	29.4 (4)
C6—C1—C7—O1	−179.7 (5)	O4ⁱ—Dy1—O5—C10	−172.7 (3)
C2—C1—C7—O1	0.2 (7)	O3ⁱⁱ—Dy1—O5—C10	130.1 (3)
C6—C5—C8—O4	−31.5 (7)	O1—Dy1—O5—C10	66.8 (4)
C4—C5—C8—O4	152.8 (4)	O8ⁱⁱⁱ—Dy1—O5—C10	−151.5 (3)
C6—C5—C8—O3	149.9 (4)	O9—Dy1—O5—C10	−21.4 (4)
C4—C5—C8—O3	−25.7 (6)	O7ⁱⁱⁱ—Dy1—O5—C10	−92.2 (3)
O8—C9—C10—O7	−6.1 (5)	O2—Dy1—O5—C10	45.3 (3)
O6—C9—C10—O7	172.8 (4)	O6—Dy1—O5—C10	−27.5 (3)
O8—C9—C10—O5	174.8 (4)	O8—C9—O6—Dy1	160.0 (4)
O6—C9—C10—O5	−6.3 (5)	C10—C9—O6—Dy1	−18.8 (4)
O2—C7—O1—Dy1	−3.7 (5)	O4ⁱ—Dy1—O6—C9	170.5 (3)
C1—C7—O1—Dy1	174.8 (4)	O3ⁱⁱ—Dy1—O6—C9	−8.6 (4)
O4ⁱ—Dy1—O1—C7	−173.2 (3)	O1—Dy1—O6—C9	−94.4 (3)
O3ⁱⁱ—Dy1—O1—C7	−88.4 (3)	O8ⁱⁱⁱ—Dy1—O6—C9	79.0 (3)
O8ⁱⁱⁱ—Dy1—O1—C7	−123.9 (3)	O9—Dy1—O6—C9	−152.0 (3)
O9—Dy1—O1—C7	105.3 (3)	O7ⁱⁱⁱ—Dy1—O6—C9	135.3 (3)
O7ⁱⁱⁱ—Dy1—O1—C7	127.2 (3)	O5—Dy1—O6—C9	23.5 (3)
O5—Dy1—O1—C7	−24.2 (3)	O2—Dy1—O6—C9	−58.0 (3)
O2—Dy1—O1—C7	2.0 (3)	O5—C10—O7—Dy1^v	−174.0 (3)
O6—Dy1—O1—C7	45.4 (3)	C9—C10—O7—Dy1^v	7.0 (5)
O1—C7—O2—Dy1	3.5 (5)	O6—C9—O8—Dy1^v	−176.7 (3)
C1—C7—O2—Dy1	−174.9 (4)	C10—C9—O8—Dy1^v	2.1 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H2W···O3^vi	0.83	2.32	2.858 (4)	123
O9—H1W···O1^vii	0.83	1.97	2.790 (4)	168
N1—H1B···O6^vii	0.89	2.63	3.379 (5)	142
N1—H1A···O8^vii	0.89	2.39	2.824 (5)	111
N1—H1A···O5^viii	0.89	1.99	2.840 (5)	160
N1—H1C···O7ⁱⁱ	0.89	1.92	2.796 (6)	169
C2—H2···O9^vii	0.93	2.55	3.421 (5)	157
C4—H4···O5ⁱⁱ	0.93	2.53	3.169 (6)	126

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

Experimental details

Crystal data
Chemical formula	[Dy(C₈H₆NO₄)(C₂O₄)(H₂O)]
M_r	448.67
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	19.951 (4), 9.3967 (18), 13.598 (3)
β (°)	118.478 (2)
V (Å³)	2240.8 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	6.72
Crystal size (mm)	0.12 × 0.11 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.499, 0.568
No. of measured, independent and observed [I > 2σ(I)] reflections	8393, 2089, 1901
R_int	0.109
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.063, 1.08
No. of reflections	2089
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.29, −1.56

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H2W···O3ⁱ	0.83	2.32	2.858 (4)	122.9
O9—H1W···O1ⁱⁱ	0.83	1.97	2.790 (4)	167.8
N1—H1B···O6ⁱⁱ	0.89	2.63	3.379 (5)	142.2
N1—H1A···O8ⁱⁱ	0.89	2.39	2.824 (5)	110.6
N1—H1A···O5ⁱⁱⁱ	0.89	1.99	2.840 (5)	160.2
N1—H1C···O7^iv	0.89	1.92	2.796 (6)	169.0
C2—H2···O9ⁱⁱ	0.93	2.55	3.421 (5)	157.0
C4—H4···O5^iv	0.93	2.53	3.169 (6)	126.0

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (20765003/B050106) and the Research Fund of Nanchang Hangkong University (No. EA200702195).

References

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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