Poly[dimethyl­ammonium [aquadi-μ2-oxalato-dysprosate(III)] trihydrate]

Ye, S.-F.; Lin, H.

doi:10.1107/S1600536810026140

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages m901-m902

https://doi.org/10.1107/S1600536810026140

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Poly[dimethylammonium [aquadi-μ₂-oxalato-dysprosate(III)] trihydrate]

Su-Fang Ye ^a and Hong Lin ^a ^*

^aJinhua Professional Technical College, Jinhua, Zhejiang 321007, People's Republic of China
^*Correspondence e-mail: jh_ll@126.com

(Received 23 June 2010; accepted 2 July 2010; online 7 July 2010)

The title compound, {(C₂H₈N)[Dy(C₂O₄)₂(H₂O)]·3H₂O}_n, was obtained as an unexpected product under hydrothermal conditions. The Dy^III atom is chelated by four oxalate anions, two of which are situated on two different centres of inversion. The distorted tricapped trigonal-prismatic coordination sphere of the Dy^III atom is completed by a water molecule. The bridging mode of the anions results in the formation of a three-dimensional network with cavities where the ammonium cations and the uncoordinated water molecules reside. The structure is stabilized by numerous N—H⋯O and O—H⋯O hydrogen-bonding interactions.

Related literature

For decomposition mechanisms of organic ligands resulting in the formation of oxalates, see: Ghosh et al. (2004 ); Zhong et al., (2008 ). For other Dy^III oxalate compounds, see: Hansson (1973 ); Kahwa et al. (1984 ); Ollendorff et al. (1969 ). The structure of the isotypic Eu^III compound was reported by Yang et al. (2005 ).

Experimental

Crystal data

(C₂H₈N)[Dy(C₂O₄)₂(H₂O)]·3H₂O
M_r = 456.70
Monoclinic, P 2₁ /c
a = 9.6239 (2) Å
b = 11.6030 (2) Å
c = 14.3050 (2) Å
β = 122.463 (1)°
V = 1347.77 (4) Å³
Z = 4
Mo Kα radiation
μ = 5.61 mm⁻¹
T = 296 K
0.19 × 0.15 × 0.04 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.374, T_max = 0.790
20173 measured reflections
3108 independent reflections
2810 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.047
S = 1.06
3108 reflections
211 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Selected bond lengths (Å)

Dy1—O3ⁱ	2.3846 (17)
Dy1—O2	2.3883 (19)
Dy1—O5	2.390 (2)
Dy1—O6	2.427 (2)
Dy1—O1	2.4335 (18)
Dy1—O4ⁱ	2.4386 (19)
Dy1—O8	2.445 (2)
Dy1—O1W	2.451 (2)
Dy1—O7	2.464 (2)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O8	0.89 (4)	2.00 (4)	2.866 (4)	163 (4)
N1—H1A⋯O1W	0.89 (4)	2.52 (4)	3.090 (4)	122 (3)
O1W—H1WA⋯O3W	0.84 (4)	2.03 (2)	2.857 (4)	173 (3)
O4W—H4WB⋯O2W	0.82 (4)	2.06 (3)	2.767 (4)	144 (5)
N1—H1B⋯O4Wⁱⁱ	0.87 (4)	1.91 (4)	2.759 (5)	165 (4)
O1W—H1WB⋯O3Wⁱⁱⁱ	0.84 (4)	1.92 (2)	2.744 (3)	167 (3)
O2W—H2WB⋯O3^iv	0.85 (4)	2.06 (2)	2.876 (4)	161 (5)
O3W—H3WA⋯O7^v	0.85 (4)	2.24 (3)	2.959 (3)	145 (4)
O3W—H3WA⋯O6^vi	0.83 (4)	2.34 (2)	3.110 (3)	156 (4)
O3W—H3WB⋯O4W^vii	0.80 (5)	2.42 (3)	2.959 (5)	125 (4)
O3W—H3WB⋯O2W^vii	0.80 (5)	2.49 (2)	3.256 (5)	160 (4)
O4W—H4WA⋯O4^viii	0.84 (4)	2.10 (3)	2.837 (4)	147 (5)
Symmetry codes: (ii) $[-x+1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (iii) -x, -y, -z-1; (iv) $[x+1, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (vi) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vii) $[x-1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (viii) -x+1, -y-1, -z.

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: SHELXTL (Sheldrick, 2008) and DIAMOND (Crystal Impact, 2008 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810026140/wm2367sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026140/wm2367Isup2.hkl

checkCIF report

Comment top

Multidentate organic ligands are usually engaged in the construction of complexes, among which oxalate is one of the simplest imaginable connectors potentially able to bridge metal ions in a bidentate chelating manner. Some dysprosium(III) oxalate compounds, such as K₈[Dy₂(C₂O₄)₇]^.14H₂O (Kahwa et al., 1984) and [Dy₂(C₂O₄)(H₂O)₆]^.4H₂O (Ollendorff et al., 1969; Hansson 1973) have been reported. Oxalates usually represent one of the main end-products of the degradation of some organic ligands, under both oxidative and nonoxidative conditions (Ghosh et al., 2004). For example, decomposition of pyridine-2,4,6-tricarboxylic acid into oxalate has been observed in the presence of cadmium(II) compounds (Zhong et al., 2008). Herein, we report a new three-dimensional oxalate structure, (C₂H₈N)[Dy(C₂O₄)₂(H₂O)].3H₂O.

A view on the molecular structure of the title compound, (I), which is isotypic with its Eu(III) analogue (Yang et al., 2005), is presented in Fig. 1. The central Dy^III atom displays a distorted tricapped trigonal-prismatic coordination by four oxalate anions and one water molecule. Each Dy^III atom is connected to four adjacent Dy^III centres through the oxalate bridges resulting in a three-dimensional polymeric network as depicted in Fig. 2. The Dy—Dy separations are 6.2135 (2), 6.2742 (2) and 6.3164 (3) Å, respectively. The cations and solvent water molecules occupy the cavities of the network and are involved in hydrogen-bonding with each other and with the network. This gives rise to a tightly held network structure.

Related literature top

For decomposition mechanisms of organic ligands resulting in the formation of oxalates, see: Ghosh et al. (2004); Zhong et al., (2008). For other Dy^III oxalate compounds, see: Hansson (1973); Kahwa et al. (1984); Ollendorff et al. (1969). The structure of the isotypic Eu(III) compound was reported by Yang et al. (2005).

Experimental top

A mixture of 2-carboxymethylsulfanyl nicotinic acid (0.086 g, 0.40 mmol), Dy₂O₃ (0.093 g, 0.25 mmol) in DMF (5 ml)/H₂O (15 ml) was placed in a 25 ml Teflon-lined stainless steel reactor and heated at 433 K for 72 h, and then cooled to room temperature over 3 days. Colourless crystals were obtained in approximate 30% yield.

Structure description top

For decomposition mechanisms of organic ligands resulting in the formation of oxalates, see: Ghosh et al. (2004); Zhong et al., (2008). For other Dy^III oxalate compounds, see: Hansson (1973); Kahwa et al. (1984); Ollendorff et al. (1969). The structure of the isotypic Eu(III) compound was reported by Yang et al. (2005).

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: SHELXTL (Sheldrick, 2008) and DIAMOND (Crystal Impact, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (1) -x, y+0.5, -z-0.5; (2) -x, -y, -z.
	Fig. 2. A view of the three-dimensional polymeric network of the title compound.

Poly[dimethylammonium [aquadi-µ₂-oxalato-dysprosate(III)] trihydrate] top

Crystal data top

(C₂H₈N)[Dy(C₂O₄)₂(H₂O)]·3H₂O	F(000) = 884
M_r = 456.70	D_x = 2.251 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9337 reflections
a = 9.6239 (2) Å	θ = 2.4–27.6°
b = 11.6030 (2) Å	µ = 5.61 mm⁻¹
c = 14.3050 (2) Å	T = 296 K
β = 122.463 (1)°	Block, colourless
V = 1347.77 (4) Å³	0.19 × 0.15 × 0.04 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3108 independent reflections
Radiation source: fine-focus sealed tube	2810 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −12→12
T_min = 0.374, T_max = 0.790	k = −15→14
20173 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) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0236P)² + 1.0326P] where P = (F_o² + 2F_c²)/3
3108 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.84 e Å⁻³
12 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

(C₂H₈N)[Dy(C₂O₄)₂(H₂O)]·3H₂O	V = 1347.77 (4) Å³
M_r = 456.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6239 (2) Å	µ = 5.61 mm⁻¹
b = 11.6030 (2) Å	T = 296 K
c = 14.3050 (2) Å	0.19 × 0.15 × 0.04 mm
β = 122.463 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	3108 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	2810 reflections with I > 2σ(I)
T_min = 0.374, T_max = 0.790	R_int = 0.032
20173 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	12 restraints
wR(F²) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.84 e Å⁻³
3108 reflections	Δρ_min = −0.91 e Å⁻³
211 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
Dy1	0.117659 (15)	−0.013113 (10)	−0.167676 (10)	0.01672 (5)
N1	0.4246 (4)	−0.1300 (3)	−0.3049 (3)	0.0407 (7)
H1A	0.393 (5)	−0.098 (3)	−0.263 (3)	0.049*
H1B	0.378 (5)	−0.095 (3)	−0.368 (3)	0.049*
O1	0.2048 (2)	−0.21224 (15)	−0.15624 (17)	0.0250 (4)
O1W	0.1053 (3)	−0.02065 (19)	−0.34320 (18)	0.0317 (5)
H1WA	0.036 (4)	−0.061 (2)	−0.396 (2)	0.038*
H1WB	0.106 (4)	0.0401 (18)	−0.375 (2)	0.038*
O2	−0.1030 (2)	−0.13712 (15)	−0.29291 (17)	0.0232 (4)
O2W	0.5505 (4)	−0.2809 (3)	−0.0349 (3)	0.0669 (9)
H2WA	0.489 (5)	−0.291 (5)	−0.009 (3)	0.080*
H2WB	0.624 (4)	−0.238 (4)	0.016 (3)	0.080*
O3	−0.1939 (2)	−0.31830 (15)	−0.32907 (16)	0.0219 (4)
O3W	−0.1188 (4)	−0.1547 (2)	−0.5332 (3)	0.0576 (8)
H3WA	−0.090 (5)	−0.222 (2)	−0.529 (4)	0.069*
H3WB	−0.209 (3)	−0.155 (3)	−0.543 (4)	0.069*
O4	0.1169 (2)	−0.39375 (16)	−0.20338 (18)	0.0278 (5)
O4W	0.6648 (5)	−0.5050 (3)	−0.0068 (3)	0.0701 (11)
H4WA	0.694 (6)	−0.530 (4)	0.056 (3)	0.084*
H4WB	0.596 (5)	−0.456 (4)	−0.020 (4)	0.084*
O5	0.3400 (3)	−0.01122 (16)	0.02214 (18)	0.0263 (5)
O6	0.0192 (3)	−0.11779 (16)	−0.06741 (17)	0.0276 (4)
O7	0.0381 (3)	0.11134 (17)	−0.06433 (18)	0.0300 (5)
O8	0.3894 (3)	−0.01101 (15)	−0.14319 (17)	0.0226 (4)
C1	0.0965 (3)	−0.2872 (2)	−0.2069 (2)	0.0197 (5)
C2	−0.0829 (3)	−0.2435 (2)	−0.2832 (2)	0.0180 (5)
C3	0.4856 (4)	−0.0001 (2)	0.0483 (2)	0.0198 (6)
C4	−0.0055 (3)	−0.0664 (2)	−0.0010 (2)	0.0220 (6)
C5	0.3567 (6)	−0.2468 (4)	−0.3333 (4)	0.0761 (15)
H5A	0.2387	−0.2431	−0.3721	0.091*
H5B	0.3984	−0.2910	−0.2667	0.091*
H5C	0.3882	−0.2827	−0.3796	0.091*
C6	0.6030 (5)	−0.1251 (5)	−0.2451 (4)	0.0710 (14)
H6A	0.6384	−0.0464	−0.2279	0.085*
H6B	0.6396	−0.1572	−0.2901	0.085*
H6C	0.6490	−0.1686	−0.1777	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Dy1	0.01578 (8)	0.01427 (7)	0.01843 (8)	−0.00014 (4)	0.00807 (6)	−0.00013 (4)
N1	0.0347 (18)	0.0526 (18)	0.0363 (17)	0.0048 (14)	0.0200 (15)	−0.0078 (14)
O1	0.0179 (11)	0.0192 (9)	0.0295 (11)	−0.0011 (8)	0.0073 (9)	−0.0039 (8)
O1W	0.0342 (14)	0.0367 (12)	0.0218 (11)	−0.0059 (10)	0.0133 (11)	−0.0019 (9)
O2	0.0213 (11)	0.0158 (9)	0.0259 (10)	0.0016 (7)	0.0082 (9)	0.0007 (8)
O2W	0.053 (2)	0.0513 (18)	0.066 (2)	0.0025 (14)	0.0119 (17)	−0.0131 (15)
O3	0.0172 (10)	0.0179 (9)	0.0272 (11)	−0.0014 (7)	0.0096 (9)	−0.0029 (7)
O3W	0.066 (2)	0.0331 (13)	0.0650 (19)	0.0039 (13)	0.0292 (19)	0.0093 (13)
O4	0.0228 (11)	0.0161 (9)	0.0319 (11)	0.0016 (8)	0.0063 (9)	−0.0012 (8)
O4W	0.074 (3)	0.068 (2)	0.0376 (18)	0.0164 (15)	0.0098 (18)	−0.0028 (14)
O5	0.0184 (11)	0.0392 (11)	0.0218 (11)	−0.0021 (8)	0.0111 (9)	−0.0007 (8)
O6	0.0340 (12)	0.0239 (10)	0.0308 (12)	−0.0039 (8)	0.0213 (10)	−0.0040 (8)
O7	0.0389 (13)	0.0241 (10)	0.0397 (13)	0.0032 (9)	0.0294 (11)	0.0059 (9)
O8	0.0177 (11)	0.0297 (10)	0.0187 (10)	−0.0005 (7)	0.0085 (9)	−0.0015 (7)
C1	0.0209 (15)	0.0194 (12)	0.0179 (13)	0.0005 (10)	0.0098 (12)	0.0006 (10)
C2	0.0197 (15)	0.0195 (12)	0.0165 (13)	−0.0014 (10)	0.0108 (12)	−0.0012 (10)
C3	0.0205 (15)	0.0161 (11)	0.0200 (14)	0.0015 (10)	0.0090 (12)	0.0005 (9)
C4	0.0157 (14)	0.0231 (14)	0.0252 (15)	−0.0009 (10)	0.0098 (12)	0.0000 (10)
C5	0.096 (4)	0.059 (3)	0.082 (4)	−0.017 (3)	0.054 (3)	−0.020 (2)
C6	0.035 (2)	0.121 (4)	0.052 (3)	0.007 (2)	0.020 (2)	−0.019 (3)

Geometric parameters (Å, º) top

Dy1—O3ⁱ	2.3846 (17)	O3W—H3WA	0.83 (3)
Dy1—O2	2.3883 (19)	O3W—H3WB	0.80 (4)
Dy1—O5	2.390 (2)	O4—C1	1.249 (3)
Dy1—O6	2.427 (2)	O4—Dy1ⁱⁱ	2.4386 (19)
Dy1—O1	2.4335 (18)	O4W—H4WA	0.84 (3)
Dy1—O4ⁱ	2.4386 (19)	O4W—H4WB	0.82 (4)
Dy1—O8	2.445 (2)	O5—C3	1.248 (4)
Dy1—O1W	2.451 (2)	O6—C4	1.248 (3)
Dy1—O7	2.464 (2)	O7—C4ⁱⁱⁱ	1.248 (3)
N1—C6	1.451 (5)	O8—C3^iv	1.246 (4)
N1—C5	1.463 (6)	C1—C2	1.551 (4)
N1—H1A	0.89 (4)	C3—O8^iv	1.246 (4)
N1—H1B	0.87 (4)	C3—C3^iv	1.549 (6)
O1—C1	1.248 (3)	C4—O7ⁱⁱⁱ	1.248 (3)
O1W—H1WA	0.84 (4)	C4—C4ⁱⁱⁱ	1.544 (5)
O1W—H1WB	0.84 (4)	C5—H5A	0.9600
O2—C2	1.245 (3)	C5—H5B	0.9600
O2W—H2WA	0.86 (5)	C5—H5C	0.9600
O2W—H2WB	0.85 (4)	C6—H6A	0.9600
O3—C2	1.254 (3)	C6—H6B	0.9600
O3—Dy1ⁱⁱ	2.3846 (17)	C6—H6C	0.9600

O3ⁱ—Dy1—O2	135.67 (6)	C5—N1—H1B	104 (3)
O3ⁱ—Dy1—O5	85.20 (6)	H1A—N1—H1B	110 (4)
O2—Dy1—O5	138.66 (7)	C1—O1—Dy1	118.16 (17)
O3ⁱ—Dy1—O6	135.05 (6)	Dy1—O1W—H1WA	121 (2)
O2—Dy1—O6	70.73 (7)	Dy1—O1W—H1WB	121 (2)
O5—Dy1—O6	74.25 (7)	H1WA—O1W—H1WB	103 (2)
O3ⁱ—Dy1—O1	143.39 (7)	C2—O2—Dy1	119.42 (17)
O2—Dy1—O1	67.30 (6)	H2WA—O2W—H2WB	99 (2)
O5—Dy1—O1	82.32 (7)	C2—O3—Dy1ⁱⁱ	118.80 (17)
O6—Dy1—O1	73.44 (7)	H3WA—O3W—H3WB	107 (3)
O3ⁱ—Dy1—O4ⁱ	67.45 (6)	C1—O4—Dy1ⁱⁱ	118.02 (17)
O2—Dy1—O4ⁱ	71.67 (6)	H4WA—O4W—H4WB	105 (3)
O5—Dy1—O4ⁱ	139.00 (7)	C3—O5—Dy1	121.19 (19)
O6—Dy1—O4ⁱ	103.57 (7)	C4—O6—Dy1	120.35 (17)
O1—Dy1—O4ⁱ	137.38 (6)	C4ⁱⁱⁱ—O7—Dy1	119.20 (17)
O3ⁱ—Dy1—O8	71.14 (6)	C3^iv—O8—Dy1	119.36 (19)
O2—Dy1—O8	124.42 (7)	O1—C1—O4	127.0 (3)
O5—Dy1—O8	66.48 (7)	O1—C1—C2	116.6 (2)
O6—Dy1—O8	130.33 (7)	O4—C1—C2	116.4 (2)
O1—Dy1—O8	72.31 (6)	O2—C2—O3	126.2 (3)
O4ⁱ—Dy1—O8	125.97 (7)	O2—C2—C1	116.7 (2)
O3ⁱ—Dy1—O1W	81.96 (7)	O3—C2—C1	117.1 (2)
O2—Dy1—O1W	71.05 (7)	O8^iv—C3—O5	127.6 (3)
O5—Dy1—O1W	133.30 (8)	O8^iv—C3—C3^iv	116.1 (3)
O6—Dy1—O1W	140.18 (7)	O5—C3—C3^iv	116.3 (3)
O1—Dy1—O1W	81.98 (7)	O7ⁱⁱⁱ—C4—O6	126.7 (3)
O4ⁱ—Dy1—O1W	74.28 (8)	O7ⁱⁱⁱ—C4—C4ⁱⁱⁱ	116.5 (3)
O8—Dy1—O1W	66.87 (7)	O6—C4—C4ⁱⁱⁱ	116.8 (3)
O3ⁱ—Dy1—O7	69.77 (6)	N1—C5—H5A	109.5
O2—Dy1—O7	111.44 (7)	N1—C5—H5B	109.5
O5—Dy1—O7	71.94 (7)	H5A—C5—H5B	109.5
O6—Dy1—O7	65.99 (7)	N1—C5—H5C	109.5
O1—Dy1—O7	136.30 (7)	H5A—C5—H5C	109.5
O4ⁱ—Dy1—O7	70.20 (7)	H5B—C5—H5C	109.5
O8—Dy1—O7	124.13 (7)	N1—C6—H6A	109.5
O1W—Dy1—O7	140.87 (7)	N1—C6—H6B	109.5
C6—N1—C5	114.3 (4)	H6A—C6—H6B	109.5
C6—N1—H1A	108 (2)	N1—C6—H6C	109.5
C5—N1—H1A	108 (2)	H6A—C6—H6C	109.5
C6—N1—H1B	112 (3)	H6B—C6—H6C	109.5

O3ⁱ—Dy1—O1—C1	−146.82 (18)	O3ⁱ—Dy1—O7—C4ⁱⁱⁱ	−163.0 (2)
O2—Dy1—O1—C1	−9.33 (19)	O2—Dy1—O7—C4ⁱⁱⁱ	64.6 (2)
O5—Dy1—O1—C1	142.0 (2)	O5—Dy1—O7—C4ⁱⁱⁱ	−71.4 (2)
O6—Dy1—O1—C1	66.3 (2)	O6—Dy1—O7—C4ⁱⁱⁱ	8.9 (2)
O4ⁱ—Dy1—O1—C1	−25.9 (2)	O1—Dy1—O7—C4ⁱⁱⁱ	−14.4 (3)
O8—Dy1—O1—C1	−150.3 (2)	O4ⁱ—Dy1—O7—C4ⁱⁱⁱ	124.6 (2)
O1W—Dy1—O1—C1	−82.1 (2)	O8—Dy1—O7—C4ⁱⁱⁱ	−114.7 (2)
O7—Dy1—O1—C1	88.5 (2)	O1W—Dy1—O7—C4ⁱⁱⁱ	150.63 (19)
O3ⁱ—Dy1—O2—C2	156.75 (18)	O3ⁱ—Dy1—O8—C3^iv	86.85 (17)
O5—Dy1—O2—C2	−34.0 (2)	O2—Dy1—O8—C3^iv	−140.12 (16)
O6—Dy1—O2—C2	−67.6 (2)	O5—Dy1—O8—C3^iv	−6.14 (16)
O1—Dy1—O2—C2	11.96 (19)	O6—Dy1—O8—C3^iv	−46.9 (2)
O4ⁱ—Dy1—O2—C2	−179.8 (2)	O1—Dy1—O8—C3^iv	−95.32 (18)
O8—Dy1—O2—C2	58.7 (2)	O4ⁱ—Dy1—O8—C3^iv	128.38 (17)
O1W—Dy1—O2—C2	101.0 (2)	O1W—Dy1—O8—C3^iv	176.00 (19)
O7—Dy1—O2—C2	−120.7 (2)	O7—Dy1—O8—C3^iv	39.15 (19)
O3ⁱ—Dy1—O5—C3	−65.25 (18)	Dy1—O1—C1—O4	−173.8 (2)
O2—Dy1—O5—C3	122.27 (18)	Dy1—O1—C1—C2	6.6 (3)
O6—Dy1—O5—C3	155.14 (19)	Dy1ⁱⁱ—O4—C1—O1	−171.9 (2)
O1—Dy1—O5—C3	80.26 (19)	Dy1ⁱⁱ—O4—C1—C2	7.7 (3)
O4ⁱ—Dy1—O5—C3	−112.15 (19)	Dy1—O2—C2—O3	166.6 (2)
O8—Dy1—O5—C3	6.26 (17)	Dy1—O2—C2—C1	−13.2 (3)
O1W—Dy1—O5—C3	9.0 (2)	Dy1ⁱⁱ—O3—C2—O2	165.2 (2)
O7—Dy1—O5—C3	−135.52 (19)	Dy1ⁱⁱ—O3—C2—C1	−15.0 (3)
O3ⁱ—Dy1—O6—C4	1.9 (3)	O1—C1—C2—O2	4.2 (4)
O2—Dy1—O6—C4	−134.4 (2)	O4—C1—C2—O2	−175.4 (2)
O5—Dy1—O6—C4	68.0 (2)	O1—C1—C2—O3	−175.6 (2)
O1—Dy1—O6—C4	154.5 (2)	O4—C1—C2—O3	4.7 (4)
O4ⁱ—Dy1—O6—C4	−69.7 (2)	Dy1—O5—C3—O8^iv	174.11 (19)
O8—Dy1—O6—C4	106.4 (2)	Dy1—O5—C3—C3^iv	−5.9 (3)
O1W—Dy1—O6—C4	−151.28 (19)	Dy1—O6—C4—O7ⁱⁱⁱ	−171.5 (2)
O7—Dy1—O6—C4	−8.9 (2)	Dy1—O6—C4—C4ⁱⁱⁱ	8.4 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O8	0.89 (4)	2.00 (4)	2.866 (4)	163 (4)
N1—H1A···O1W	0.89 (4)	2.52 (4)	3.090 (4)	122 (3)
O1W—H1WA···O3W	0.84 (4)	2.03 (2)	2.857 (4)	173 (3)
O4W—H4WB···O2W	0.82 (4)	2.06 (3)	2.767 (4)	144 (5)
N1—H1B···O4W^v	0.87 (4)	1.91 (4)	2.759 (5)	165 (4)
O1W—H1WB···O3W^vi	0.84 (4)	1.92 (2)	2.744 (3)	167 (3)
O2W—H2WB···O3^vii	0.85 (4)	2.06 (2)	2.876 (4)	161 (5)
O3W—H3WA···O7ⁱⁱ	0.85 (4)	2.24 (3)	2.959 (3)	145 (4)
O3W—H3WA···O6^viii	0.83 (4)	2.34 (2)	3.110 (3)	156 (4)
O3W—H3WB···O4W^ix	0.80 (5)	2.42 (3)	2.959 (5)	125 (4)
O3W—H3WB···O2W^ix	0.80 (5)	2.49 (2)	3.256 (5)	160 (4)
O4W—H4WA···O4^x	0.84 (4)	2.10 (3)	2.837 (4)	147 (5)

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

Experimental details

Crystal data
Chemical formula	(C₂H₈N)[Dy(C₂O₄)₂(H₂O)]·3H₂O
M_r	456.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.6239 (2), 11.6030 (2), 14.3050 (2)
β (°)	122.463 (1)
V (Å³)	1347.77 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.61
Crystal size (mm)	0.19 × 0.15 × 0.04

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.374, 0.790
No. of measured, independent and observed [I > 2σ(I)] reflections	20173, 3108, 2810
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.047, 1.06
No. of reflections	3108
No. of parameters	211
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.91

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Crystal Impact, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Dy1—O3ⁱ	2.3846 (17)	Dy1—O4ⁱ	2.4386 (19)
Dy1—O2	2.3883 (19)	Dy1—O8	2.445 (2)
Dy1—O5	2.390 (2)	Dy1—O1W	2.451 (2)
Dy1—O6	2.427 (2)	Dy1—O7	2.464 (2)
Dy1—O1	2.4335 (18)

Symmetry code: (i) −x, 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—H1A···O8	0.89 (4)	2.00 (4)	2.866 (4)	163 (4)
N1—H1A···O1W	0.89 (4)	2.52 (4)	3.090 (4)	122 (3)
O1W—H1WA···O3W	0.84 (4)	2.027 (19)	2.857 (4)	173 (3)
O4W—H4WB···O2W	0.82 (4)	2.06 (3)	2.767 (4)	144 (5)
N1—H1B···O4Wⁱⁱ	0.87 (4)	1.91 (4)	2.759 (5)	165 (4)
O1W—H1WB···O3Wⁱⁱⁱ	0.84 (4)	1.92 (2)	2.744 (3)	167 (3)
O2W—H2WB···O3^iv	0.85 (4)	2.06 (2)	2.876 (4)	161 (5)
O3W—H3WA···O7^v	0.85 (4)	2.24 (3)	2.959 (3)	145 (4)
O3W—H3WA···O6^vi	0.83 (4)	2.34 (2)	3.110 (3)	156 (4)
O3W—H3WB···O4W^vii	0.80 (5)	2.42 (3)	2.959 (5)	125 (4)
O3W—H3WB···O2W^vii	0.80 (5)	2.49 (2)	3.256 (5)	160 (4)
O4W—H4WA···O4^viii	0.84 (4)	2.10 (3)	2.837 (4)	147 (5)

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

References

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Volume 66| Part 8| August 2010| Pages m901-m902

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