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

Lv, Y.-K.; Gan, L.-H.; Xu, L.; Zheng, H.-W.; Liu, C.

doi:10.1107/S1600536811019209

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages m837-m838

doi:10.1107/S1600536811019209

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

Yao-Kang Lv,^a Li-Hua Gan,^a ^* Liang Xu,^a Hao-Wen Zheng ^a and Cao Liu ^a

^aDepartment of Chemistry, Tongji University, Shanghai 200092, People's Republic of China
^*Correspondence e-mail: ganlh@tongji.edu.cn

(Received 11 May 2011; accepted 20 May 2011; online 4 June 2011)

The title complex, {(C₂H₈N)[Y(C₂O₄)₂(H₂O)]·3H₂O}_n, was obtained accidentally under hydrothermal conditions. The Y^III atom is chelated by four oxalate ligands and one water molecule resulting in a distorted tricapped trigonal–prismatic geometry. Each oxalate ligand bridges two Y^III atoms, thus generating a three-dimensional network with cavities in which the ammonium cations and lattice water molecules reside. Various O—H⋯O and N—H⋯O hydrogen-bonding interactions stabilize the crystal structure. The title complex is isotypic with the Eu and Dy analogues.

Related literature

For general background to the rational design and synthesis of metal-organic polymers, see: Lv et al. (2010 , 2011 ). For related structures, see: Platel et al. (2009 ); Gao & Cui (2008 ); Deguenon et al. (1990 ). The structure of the isotypic Eu^III compound was reported by Yang et al. (2005 ), and that of the Dy^III compound by Ye & Lin (2010 ). For decomposition products obtained under hydrothermal conditions, see: Song et al. (2004 ).

Experimental

Crystal data

(C₂H₈N)[Y(C₂O₄)₂(H₂O)]·3H₂O
M_r = 383.11
Monoclinic, P 2₁ /c
a = 9.6008 (1) Å
b = 11.5422 (2) Å
c = 14.2886 (2) Å
β = 122.460 (1)°
V = 1336.00 (3) Å³
Z = 4
Mo Kα radiation
μ = 4.43 mm⁻¹
T = 293 K
0.31 × 0.20 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.36, T_max = 0.43
11935 measured reflections
3040 independent reflections
2384 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.082
S = 1.00
3040 reflections
207 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2Wⁱ	0.83 (2)	1.93 (2)	2.742 (4)	167 (4)
O1W—H1WB⋯O2Wⁱⁱ	0.72 (2)	2.20 (2)	2.861 (4)	152 (4)
O2W—H2WA⋯O6ⁱⁱⁱ	0.81 (2)	2.38 (2)	3.143 (4)	158 (5)
O2W—H2WA⋯O7^iv	0.81 (2)	2.45 (5)	2.944 (4)	121 (5)
O2W—H2WB⋯O3W^v	0.79 (2)	2.38 (3)	2.963 (7)	131 (4)
O2W—H2WB⋯O4W	0.79 (2)	2.44 (3)	3.194 (6)	159 (5)
O3W—H3WA⋯O2	0.88 (2)	2.36 (7)	2.830 (5)	114 (6)
O3W—H3WB⋯O4W^iv	0.86 (2)	1.90 (3)	2.735 (6)	161 (6)
O4W—H4WA⋯O1^vi	0.82 (2)	2.13 (2)	2.943 (4)	172 (5)
O4W—H4WB⋯O3^vii	0.83 (2)	2.08 (3)	2.857 (4)	155 (6)
N1—H1A⋯O8^vi	0.90	2.00	2.869 (4)	163
N1—H1A⋯O1W^vi	0.90	2.54	3.107 (4)	122
N1—H1B⋯O3W	0.90	1.90	2.784 (6)	166
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x-1, y, z-1; (iii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (vii) x+1, y, z+1.

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: DIAMOND (Brandenburg & Putz, 2004 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019209/wm2489sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019209/wm2489Isup2.hkl

checkCIF report

Comment top

Rational design and synthesis of metal-organic polymers have attracted much attention in the field of supramolecular chemistry and crystal engineering (Lv et al., 2010; 2011). Oxalate, which usually represent one of the products of the degradation of some organic compounds, is one of the simplest multidentate organic ligands potentially able to bridge metal ions in a bidentate chelating manner (Deguenon et al., 1990). Herein, we report the synthesis and structure of a novel yttrium(III) complex, (C₂H₈N)[Y(C₂O₄)₂(H₂O)]^.3H₂O, (I).

Complex (I) is isotypic with its Eu(III) (Yang et al., 2005) and Dy(III) (Ye & Lin, 2010) analogues. As shown in Fig. 1, the Y^III atom is chelated by four oxalate ligands and one water molecule resulting in a distorted tricapped trigonal-prismatic coordination environment. The Y—O bond lengths fall in the range of 2.374 (2)-2.459 (2) Å, which is in agreement with comparable values reported elsewhere (Platel et al., 2009; Gao & Cui, 2008). Each oxalate ligand bridges two Y^III atoms, thus generating a three-dimensional network with cavities where the ammonium cations and lattice water molecules reside (Fig. 2). Furthermore, there are various hydrogen-bonding interactions (N—H···O and O—H···O), involving the lattice water molecules and the cations, which give rise to a tightly held network structure.

Related literature top

For general background to the rational design and synthesis of metal-organic polymers, see: Lv et al. (2010, 2011). For related structures, see: Platel et al. (2009); Gao & Cui, (2008); Deguenon et al. (1990). The structure of the isotypic Eu^III compound was reported by Yang et al. (2005), and that of the Dy^III compound by Ye & Lin (2010). For decomposition products obtained under hydrothermal conditions, see: Song et al. (2004).

Experimental top

A mixture of D-saccharic acid potassium salt (0.248 g, 1.0 mmol), Y(NO₃)₃^.6H₂O (0.191 g, 0.5 mmol) and N,N-dimethylformamide (20 ml) was stirred and heated at 373 K for 1 hour. The resulted colorless solution was kept at 293 K. Colorless block-shaped crystals of the title compound suitable for X-ray crystallographic study were obtained via slow evaporation within 2 weeks.

It is most likely that the oxalate ligands in this complex originates from the decomposition of the potassium salt of D-saccharic acid, and the protonated dimethylamine cations compensating the negative charge of the anionic network are believed to result from decomposition of the N,N-dimethylformamide solvent (Song et al., 2004; Ye & Lin, 2010).

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: DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. An expanded vioew of the asymmetric unit of (I), showing the coordination of the Y^III atom, and the presence of the lattice water molecules and the ammonium cation. All hydrogen atoms were omitted for clarity. [Symmetry codes: (i) -x + 1, y + 1/2, -z + 1/2; (ii) -x + 1, -y + 2, -z + 1; (iii) -x + 2, -y + 2, -z + 1.]
	Fig. 2. View of the three-dimensional framework of (I). All hydrogen atoms are omitted for clarity. Hydrogen bonding between donator and acceptor atoms is indicated by dashed lines.

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

Crystal data top

(C₂H₈N)[Y(C₂O₄)₂(H₂O)]·3H₂O	F(000) = 776
M_r = 383.11	D_x = 1.905 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2287 reflections
a = 9.6008 (1) Å	θ = 2.0–28.0°
b = 11.5422 (2) Å	µ = 4.43 mm⁻¹
c = 14.2886 (2) Å	T = 293 K
β = 122.460 (1)°	Block, colourless
V = 1336.00 (3) Å³	0.31 × 0.20 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3040 independent reflections
Radiation source: fine-focus sealed tube	2384 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.36, T_max = 0.43	k = −14→14
11935 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0359P)² + 1.2217P] where P = (F_o² + 2F_c²)/3
3040 reflections	(Δ/σ)_max = 0.001
207 parameters	Δρ_max = 0.70 e Å⁻³
13 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

(C₂H₈N)[Y(C₂O₄)₂(H₂O)]·3H₂O	V = 1336.00 (3) Å³
M_r = 383.11	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6008 (1) Å	µ = 4.43 mm⁻¹
b = 11.5422 (2) Å	T = 293 K
c = 14.2886 (2) Å	0.31 × 0.20 × 0.19 mm
β = 122.460 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	3040 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2384 reflections with I > 2σ(I)
T_min = 0.36, T_max = 0.43	R_int = 0.044
11935 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	13 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.70 e Å⁻³
3040 reflections	Δρ_min = −0.58 e Å⁻³
207 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
Y1	0.61770 (3)	0.98846 (2)	0.33257 (2)	0.01817 (10)
O1	0.7049 (3)	0.78990 (17)	0.34286 (19)	0.0270 (5)
O2	0.6167 (3)	0.60733 (18)	0.2950 (2)	0.0304 (6)
O3	0.3054 (3)	0.68334 (17)	0.17013 (18)	0.0231 (5)
O4	0.3959 (3)	0.86535 (17)	0.20743 (19)	0.0259 (5)
O6	0.5198 (3)	0.88268 (18)	0.4319 (2)	0.0293 (5)
O7	0.5387 (3)	1.11238 (19)	0.4367 (2)	0.0320 (6)
O8	0.8892 (3)	0.99123 (17)	0.35640 (19)	0.0245 (5)
O9	0.8389 (3)	0.98964 (18)	0.52152 (19)	0.0278 (5)
O1W	0.6044 (3)	0.9808 (2)	0.1578 (2)	0.0348 (6)
H1WA	0.617 (5)	1.039 (2)	0.129 (3)	0.042*
H1WB	0.568 (4)	0.931 (2)	0.122 (3)	0.042*
O2W	1.3774 (5)	0.8468 (3)	0.9672 (3)	0.0649 (10)
H2WA	1.386 (6)	0.785 (3)	0.946 (4)	0.078*
H2WB	1.293 (4)	0.850 (4)	0.965 (5)	0.078*
O3W	0.8383 (7)	0.5082 (4)	0.5055 (4)	0.1038 (17)
H3WA	0.857 (10)	0.539 (5)	0.457 (5)	0.125*
H3WB	0.889 (8)	0.444 (3)	0.512 (6)	0.125*
O4W	1.0523 (5)	0.7844 (3)	0.9661 (3)	0.0861 (13)
H4WA	0.959 (3)	0.758 (5)	0.936 (4)	0.103*
H4WB	1.103 (6)	0.758 (5)	1.030 (2)	0.103*
N1	0.9245 (4)	0.6326 (3)	0.6962 (3)	0.0585 (11)
H1A	0.8928	0.6007	0.7394	0.070*
H1B	0.8808	0.5895	0.6341	0.070*
C1	0.5960 (4)	0.7148 (2)	0.2919 (3)	0.0222 (7)
C2	0.4163 (4)	0.7587 (2)	0.2166 (3)	0.0195 (6)
C3	0.4947 (4)	0.9335 (3)	0.4984 (3)	0.0243 (7)
C4	1.0151 (4)	1.0005 (2)	0.4524 (3)	0.0202 (6)
C5	1.0993 (6)	0.6253 (6)	0.7531 (5)	0.0864 (19)
H5A	1.1314	0.5459	0.7567	0.104*
H5B	1.1476	0.6553	0.8269	0.104*
H5C	1.1370	0.6699	0.7141	0.104*
C6	0.8547 (8)	0.7488 (5)	0.6652 (5)	0.0897 (19)
H6A	0.7365	0.7442	0.6254	0.108*
H6B	0.8872	0.7841	0.6190	0.108*
H6C	0.8944	0.7946	0.7309	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Y1	0.01775 (15)	0.01434 (15)	0.01968 (16)	−0.00007 (11)	0.00824 (12)	−0.00024 (11)
O1	0.0193 (12)	0.0194 (11)	0.0322 (14)	−0.0013 (8)	0.0071 (11)	−0.0044 (9)
O2	0.0264 (12)	0.0173 (11)	0.0332 (14)	0.0029 (9)	0.0066 (11)	−0.0002 (9)
O3	0.0203 (11)	0.0193 (10)	0.0265 (13)	−0.0017 (8)	0.0105 (10)	−0.0016 (9)
O4	0.0232 (12)	0.0170 (10)	0.0285 (13)	0.0016 (8)	0.0079 (10)	0.0003 (9)
O6	0.0347 (13)	0.0252 (12)	0.0331 (15)	−0.0039 (9)	0.0216 (12)	−0.0047 (10)
O7	0.0424 (14)	0.0252 (12)	0.0402 (16)	0.0045 (10)	0.0301 (13)	0.0060 (10)
O8	0.0195 (10)	0.0307 (12)	0.0205 (11)	0.0009 (9)	0.0088 (9)	−0.0019 (9)
O9	0.0209 (11)	0.0368 (13)	0.0265 (12)	−0.0014 (9)	0.0132 (10)	−0.0004 (10)
O1W	0.0408 (14)	0.0346 (14)	0.0265 (14)	−0.0076 (12)	0.0165 (12)	−0.0043 (11)
O2W	0.080 (3)	0.0390 (17)	0.069 (2)	0.0025 (16)	0.036 (2)	0.0072 (16)
O3W	0.112 (4)	0.095 (3)	0.061 (3)	0.031 (3)	0.017 (3)	−0.013 (2)
O4W	0.070 (3)	0.061 (2)	0.069 (3)	−0.0094 (19)	−0.001 (2)	0.0154 (19)
N1	0.045 (2)	0.071 (3)	0.058 (3)	−0.0039 (18)	0.027 (2)	0.022 (2)
C1	0.0233 (16)	0.0187 (15)	0.0242 (17)	0.0003 (11)	0.0124 (14)	−0.0014 (12)
C2	0.0236 (17)	0.0206 (15)	0.0165 (16)	−0.0012 (11)	0.0121 (14)	−0.0026 (12)
C3	0.0184 (14)	0.0272 (17)	0.0257 (17)	−0.0012 (12)	0.0108 (13)	−0.0008 (13)
C4	0.0205 (14)	0.0145 (14)	0.0222 (16)	0.0004 (11)	0.0092 (13)	−0.0013 (12)
C5	0.046 (3)	0.144 (6)	0.066 (4)	−0.004 (3)	0.028 (3)	0.027 (4)
C6	0.110 (5)	0.073 (4)	0.103 (5)	0.024 (3)	0.068 (4)	0.029 (3)

Geometric parameters (Å, º) top

Y1—O3ⁱ	2.374 (2)	O2W—H2WA	0.805 (19)
Y1—O9	2.376 (2)	O2W—H2WB	0.794 (19)
Y1—O4	2.380 (2)	O3W—H3WA	0.88 (2)
Y1—O6	2.413 (2)	O3W—H3WB	0.86 (2)
Y1—O1	2.417 (2)	O4W—H4WA	0.82 (2)
Y1—O2ⁱ	2.422 (2)	O4W—H4WB	0.83 (2)
Y1—O1W	2.432 (3)	N1—C5	1.421 (6)
Y1—O8	2.441 (2)	N1—C6	1.458 (6)
Y1—O7	2.459 (2)	N1—H1A	0.9000
O1—C1	1.247 (3)	N1—H1B	0.9000
O2—C1	1.254 (3)	C1—C2	1.548 (4)
O2—Y1ⁱⁱ	2.422 (2)	C3—O7ⁱⁱⁱ	1.250 (4)
O3—C2	1.254 (3)	C3—C3ⁱⁱⁱ	1.536 (6)
O3—Y1ⁱⁱ	2.374 (2)	C4—O9^iv	1.248 (4)
O4—C2	1.243 (3)	C4—C4^iv	1.535 (6)
O6—C3	1.246 (4)	C5—H5A	0.9600
O7—C3ⁱⁱⁱ	1.250 (4)	C5—H5B	0.9600
O8—C4	1.255 (4)	C5—H5C	0.9600
O9—C4^iv	1.248 (4)	C6—H6A	0.9600
O1W—H1WA	0.828 (18)	C6—H6B	0.9600
O1W—H1WB	0.720 (17)	C6—H6C	0.9600

O3ⁱ—Y1—O9	85.24 (7)	C3—O6—Y1	120.4 (2)
O3ⁱ—Y1—O4	135.57 (7)	C3ⁱⁱⁱ—O7—Y1	119.2 (2)
O9—Y1—O4	138.66 (8)	C4—O8—Y1	118.9 (2)
O3ⁱ—Y1—O6	135.37 (8)	C4^iv—O9—Y1	121.0 (2)
O9—Y1—O6	74.17 (8)	Y1—O1W—H1WA	122 (3)
O4—Y1—O6	70.48 (8)	Y1—O1W—H1WB	119 (3)
O3ⁱ—Y1—O1	143.01 (7)	H1WA—O1W—H1WB	117 (3)
O9—Y1—O1	82.37 (7)	H2WA—O2W—H2WB	110 (3)
O4—Y1—O1	67.70 (7)	H3WA—O3W—H3WB	95 (7)
O6—Y1—O1	73.50 (8)	H4WA—O4W—H4WB	106 (3)
O3ⁱ—Y1—O2ⁱ	67.82 (7)	C5—N1—C6	115.9 (5)
O9—Y1—O2ⁱ	139.01 (8)	C5—N1—H1A	108.3
O4—Y1—O2ⁱ	71.18 (7)	C6—N1—H1A	108.3
O6—Y1—O2ⁱ	103.39 (8)	C5—N1—H1B	108.3
O1—Y1—O2ⁱ	137.25 (7)	C6—N1—H1B	108.3
O3ⁱ—Y1—O1W	82.13 (8)	H1A—N1—H1B	107.4
O9—Y1—O1W	133.57 (8)	O1—C1—O2	126.8 (3)
O4—Y1—O1W	70.99 (8)	O1—C1—C2	116.8 (2)
O6—Y1—O1W	139.75 (8)	O2—C1—C2	116.4 (3)
O1—Y1—O1W	81.59 (8)	O4—C2—O3	126.2 (3)
O2ⁱ—Y1—O1W	74.46 (9)	O4—C2—C1	116.8 (3)
O3ⁱ—Y1—O8	70.84 (7)	O3—C2—C1	117.0 (3)
O9—Y1—O8	66.75 (7)	O6—C3—O7ⁱⁱⁱ	126.7 (3)
O4—Y1—O8	124.78 (8)	O6—C3—C3ⁱⁱⁱ	117.1 (4)
O6—Y1—O8	130.44 (8)	O7ⁱⁱⁱ—C3—C3ⁱⁱⁱ	116.2 (4)
O1—Y1—O8	72.24 (7)	O9^iv—C4—O8	127.1 (3)
O2ⁱ—Y1—O8	126.06 (8)	O9^iv—C4—C4^iv	116.9 (3)
O1W—Y1—O8	66.89 (8)	O8—C4—C4^iv	116.0 (3)
O3ⁱ—Y1—O7	70.02 (7)	N1—C5—H5A	109.5
O9—Y1—O7	71.75 (8)	N1—C5—H5B	109.5
O4—Y1—O7	111.09 (8)	H5A—C5—H5B	109.5
O6—Y1—O7	66.06 (8)	N1—C5—H5C	109.5
O1—Y1—O7	136.38 (8)	H5A—C5—H5C	109.5
O2ⁱ—Y1—O7	70.27 (8)	H5B—C5—H5C	109.5
O1W—Y1—O7	141.16 (8)	N1—C6—H6A	109.5
O8—Y1—O7	124.12 (8)	N1—C6—H6B	109.5
C1—O1—Y1	117.95 (18)	H6A—C6—H6B	109.5
C1—O2—Y1ⁱⁱ	117.94 (19)	N1—C6—H6C	109.5
C2—O3—Y1ⁱⁱ	118.85 (19)	H6A—C6—H6C	109.5
C2—O4—Y1	119.03 (19)	H6B—C6—H6C	109.5

O3ⁱ—Y1—O1—C1	−146.8 (2)	O3ⁱ—Y1—O8—C4	87.9 (2)
O9—Y1—O1—C1	141.7 (2)	O9—Y1—O8—C4	−5.14 (19)
O4—Y1—O1—C1	−9.2 (2)	O4—Y1—O8—C4	−139.29 (19)
O6—Y1—O1—C1	66.0 (2)	O6—Y1—O8—C4	−46.0 (2)
O2ⁱ—Y1—O1—C1	−26.0 (3)	O1—Y1—O8—C4	−94.3 (2)
O1W—Y1—O1—C1	−82.0 (2)	O2ⁱ—Y1—O8—C4	129.6 (2)
O8—Y1—O1—C1	−150.3 (3)	O1W—Y1—O8—C4	177.4 (2)
O7—Y1—O1—C1	88.5 (3)	O7—Y1—O8—C4	40.2 (2)
O3ⁱ—Y1—O4—C2	156.4 (2)	O3ⁱ—Y1—O9—C4^iv	−65.9 (2)
O9—Y1—O4—C2	−35.0 (3)	O4—Y1—O9—C4^iv	122.1 (2)
O6—Y1—O4—C2	−67.7 (2)	O6—Y1—O9—C4^iv	154.1 (2)
O1—Y1—O4—C2	11.9 (2)	O1—Y1—O9—C4^iv	79.1 (2)
O2ⁱ—Y1—O4—C2	179.9 (3)	O2ⁱ—Y1—O9—C4^iv	−113.6 (2)
O1W—Y1—O4—C2	100.4 (2)	O1W—Y1—O9—C4^iv	8.5 (3)
O8—Y1—O4—C2	58.5 (3)	O8—Y1—O9—C4^iv	5.23 (19)
O7—Y1—O4—C2	−121.0 (2)	O7—Y1—O9—C4^iv	−136.5 (2)
O3ⁱ—Y1—O6—C3	2.2 (3)	Y1—O1—C1—O2	−173.7 (3)
O9—Y1—O6—C3	68.0 (2)	Y1—O1—C1—C2	6.4 (4)
O4—Y1—O6—C3	−133.8 (3)	Y1ⁱⁱ—O2—C1—O1	−172.3 (3)
O1—Y1—O6—C3	154.5 (3)	Y1ⁱⁱ—O2—C1—C2	7.6 (4)
O2ⁱ—Y1—O6—C3	−69.7 (2)	Y1—O4—C2—O3	167.4 (2)
O1W—Y1—O6—C3	−151.3 (2)	Y1—O4—C2—C1	−13.2 (4)
O8—Y1—O6—C3	106.6 (2)	Y1ⁱⁱ—O3—C2—O4	165.7 (3)
O7—Y1—O6—C3	−8.7 (2)	Y1ⁱⁱ—O3—C2—C1	−13.8 (4)
O3ⁱ—Y1—O7—C3ⁱⁱⁱ	−163.4 (3)	O1—C1—C2—O4	4.4 (4)
O9—Y1—O7—C3ⁱⁱⁱ	−71.8 (2)	O2—C1—C2—O4	−175.5 (3)
O4—Y1—O7—C3ⁱⁱⁱ	64.3 (3)	O1—C1—C2—O3	−176.1 (3)
O6—Y1—O7—C3ⁱⁱⁱ	8.5 (2)	O2—C1—C2—O3	4.0 (4)
O1—Y1—O7—C3ⁱⁱⁱ	−15.1 (3)	Y1—O6—C3—O7ⁱⁱⁱ	−171.9 (3)
O2ⁱ—Y1—O7—C3ⁱⁱⁱ	123.9 (3)	Y1—O6—C3—C3ⁱⁱⁱ	8.3 (5)
O1W—Y1—O7—C3ⁱⁱⁱ	149.8 (2)	Y1—O8—C4—O9^iv	−175.3 (2)
O8—Y1—O7—C3ⁱⁱⁱ	−115.3 (2)	Y1—O8—C4—C4^iv	4.7 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2W^iv	0.83 (2)	1.93 (2)	2.742 (4)	167 (4)
O1W—H1WB···O2W^v	0.72 (2)	2.20 (2)	2.861 (4)	152 (4)
O2W—H2WA···O6^vi	0.81 (2)	2.38 (2)	3.143 (4)	158 (5)
O2W—H2WA···O7^vii	0.81 (2)	2.45 (5)	2.944 (4)	121 (5)
O2W—H2WB···O3W^viii	0.79 (2)	2.38 (3)	2.963 (7)	131 (4)
O2W—H2WB···O4W	0.79 (2)	2.44 (3)	3.194 (6)	159 (5)
O3W—H3WA···O2	0.88 (2)	2.36 (7)	2.830 (5)	114 (6)
O3W—H3WB···O4W^vii	0.86 (2)	1.90 (3)	2.735 (6)	161 (6)
O4W—H4WA···O1^ix	0.82 (2)	2.13 (2)	2.943 (4)	172 (5)
O4W—H4WB···O3^x	0.83 (2)	2.08 (3)	2.857 (4)	155 (6)
N1—H1A···O8^ix	0.90	2.00	2.869 (4)	163
N1—H1A···O1W^ix	0.90	2.54	3.107 (4)	122
N1—H1B···O3W	0.90	1.90	2.784 (6)	166

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

Experimental details

Crystal data
Chemical formula	(C₂H₈N)[Y(C₂O₄)₂(H₂O)]·3H₂O
M_r	383.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.6008 (1), 11.5422 (2), 14.2886 (2)
β (°)	122.460 (1)
V (Å³)	1336.00 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.43
Crystal size (mm)	0.31 × 0.20 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.36, 0.43
No. of measured, independent and observed [I > 2σ(I)] reflections	11935, 3040, 2384
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.082, 1.00
No. of reflections	3040
No. of parameters	207
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.58

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2Wⁱ	0.828 (18)	1.93 (2)	2.742 (4)	167 (4)
O1W—H1WB···O2Wⁱⁱ	0.720 (17)	2.20 (2)	2.861 (4)	152 (4)
O2W—H2WA···O6ⁱⁱⁱ	0.805 (19)	2.38 (2)	3.143 (4)	158 (5)
O2W—H2WA···O7^iv	0.805 (19)	2.45 (5)	2.944 (4)	121 (5)
O2W—H2WB···O3W^v	0.794 (19)	2.38 (3)	2.963 (7)	131 (4)
O2W—H2WB···O4W	0.794 (19)	2.44 (3)	3.194 (6)	159 (5)
O3W—H3WA···O2	0.88 (2)	2.36 (7)	2.830 (5)	114 (6)
O3W—H3WB···O4W^iv	0.86 (2)	1.90 (3)	2.735 (6)	161 (6)
O4W—H4WA···O1^vi	0.82 (2)	2.13 (2)	2.943 (4)	172 (5)
O4W—H4WB···O3^vii	0.83 (2)	2.08 (3)	2.857 (4)	155 (6)
N1—H1A···O8^vi	0.90	2.00	2.869 (4)	163
N1—H1A···O1W^vi	0.90	2.54	3.107 (4)	122
N1—H1B···O3W	0.90	1.90	2.784 (6)	166

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

Acknowledgements

The present work was supported financially by the National Natural Science Foundation of China (No. 20973127) and Shanghai Nanotechnology Promotion Center (No. 0952nm00800).

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