A one-dimensional ladder-like coordination polymer: poly[[hexa­aqua­bis(μ-5-nitro­benzene-1,3-dicarboxyl­ato-κ3O,O′,O′′)(μ-oxalato-κ4O,O′:O′′,O′′′)diyttrium(III)] trihydrate]

Fu, Z.; Lin, Y.; Zhou, Y.-Y.; Zhang, H.-T.

doi:10.1107/S1600536807064306

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages m120-m121

https://doi.org/10.1107/S1600536807064306

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A one-dimensional ladder-like coordination polymer: poly[[hexaaquabis(μ-5-nitrobenzene-1,3-dicarboxylato-κ³O,O′,O′′)(μ-oxalato-κ⁴O,O′:O′′,O′′′)diyttrium(III)] trihydrate]

Zhong Fu,^a Ying Lin,^a Yun-You Zhou ^a and Hong-Tao Zhang ^a ^*

^aCollege of Chemistry and Materials Science, Anhui Key Laboratory of Functional Molecular Solids, Anhui Normal University, Wuhu 241000, People's Republic of China
^*Correspondence e-mail: zht2006@mail.ahnu.edu.cn

(Received 14 November 2007; accepted 29 November 2007; online 6 December 2007)

In the crystal structure of the title one-dimensional coordination polymer, [Y₂(C₈H₃NO₆)₂(C₂O₄)(H₂O)₆]·3H₂O, each Y^III ion is bridged to its neighbours by two 5-nitrobenzene-1,3-dicarboxylate (nbdc) dianions and one oxalate dianion (located on an inversion centre) to form a ladder-like polymeric structure. The two carboxylate groups of nbdc assume different modes of coordination, one is chelating whereas the other is monodentate. Three water molecules coordinate to the Y^III ion to complete an eight-coordinate distorted dodecahedral geometry. The ladder-like polymers are assembled together by hydrogen bonding and π–π stacking [centrio–centriod distance = 3.819 (9) Å] in the crystal structure.

Related literature

For general background, see: Biradha (2003 ); Braga et al. (2005 ); Burrows et al. (2003 ); Kongshaug & Fjellvag (2006 ); Moulton & Zaworotko (2001 ); Ohmori et al. (2004 ); Tang et al. (2006 ); Janiak (2003 ). For related structures, see: Thomas et al. (2002 ); Nordell et al. (2003 ); Janiak (2000 ). For related literature, see: Ren et al. (2006 ); Si et al. (2004 ).

Experimental

Crystal data

[Y₂(C₈H₃NO₆)₂(C₂O₄)(H₂O)₆]·3H₂O
M_r = 846.21
Triclinic, $[P \overline 1]$
a = 7.4270 (15) Å
b = 9.2070 (18) Å
c = 11.522 (2) Å
α = 74.16 (3)°
β = 71.76 (3)°
γ = 80.01 (2)°
V = 716.5 (3) Å³
Z = 1
Mo Kα radiation
μ = 4.14 mm⁻¹
T = 298 (2) K
0.20 × 0.15 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 ) T_min = 0.48, T_max = 0.60
3018 measured reflections
2785 independent reflections
2260 reflections with I > 2σ(I)
R_int = 0.097
3 standard reflections every 200 reflections intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.112
S = 1.05
2785 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Selected bond lengths (Å)

O1—Y	2.414 (4)
O2—Y	2.424 (4)
O3—Yⁱ	2.299 (3)
O7—Yⁱⁱ	2.365 (3)
O8—Y	2.361 (3)
O9—Y	2.314 (4)
O10—Y	2.336 (4)
O11—Y	2.311 (4)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9A⋯O2ⁱⁱⁱ	0.85	2.14	2.735 (5)	127
O9—H9B⋯O4^iv	0.85	2.07	2.726 (5)	134
O10—H10A⋯O6ⁱⁱⁱ	0.85	2.36	3.115 (7)	148
O10—H10B⋯O12ⁱⁱ	0.85	2.30	2.778 (6)	116
O10—H10B⋯O12ⁱⁱ	0.85	2.30	2.778 (6)	116
O11—H11A⋯O4^v	0.85	2.09	2.694 (5)	127
O11—H11B⋯O5^vi	0.85	2.57	2.987 (6)	111
O11—H11B⋯O7^vii	0.85	2.23	2.784 (5)	123
O12—H12A⋯O1	0.85	2.11	2.841 (6)	144
O12—H12B⋯O10ⁱ	0.85	2.21	2.953 (6)	147
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1; (iii) -x+1, -y, -z; (iv) x+1, y-1, z; (v) x, y-1, z; (vi) -x, -y+1, -z; (vii) x-1, y, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807064306/xu2377sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064306/xu2377Isup2.hkl

checkCIF report

Comment top

There is an intense research interest for the crystal engineering of coordination polymers owing to their intriguing molecular topologies, such as molecular grids, ladders, rings, diamondoids and honeycombs, and potential applications as functional materials (Biradha, 2003; Braga et al., 2005; Janiak, 2003; Ohmori et al., 2004). In order to construct the infinite structure, plentiful multidentate organic ligands are used to bridge metal ions (Moulton & Zaworotko, 2001). Among them, V-shape molecules, such as isophthalic acid and 5-amino-isophthalic acid, have received much attention because such a molecular geometry can result in unexpected structure comparing with that constructed by linear ligands (Burrows et al., 2003; Tang et al., 2006; Kongshaug & Fjellvag, 2006; Si et al., 2004; Ren et al., 2006). Herein, we present a novel ladder-like coordination polymer (I): Y₂(C₈H₃NO₆)₂(C₂O₄)(H₂O)₆.3(H₂O), in which metal ions are bridged by a V-shape ligand, 5-nitrobenzene-1,3-dicarboxylate (5-nitroisophthalate, abbreviated as 5-NIP), and oxalate ligands.

As shown in Figure 1, the Y(III) ion adopts an eight-coordinate geometry which may be described as a distorted dodecahedron (Table 1): it is bounded to three water oxygen atoms (O9, O10 and O11) and five carboxylate oxygen atoms, in which O1, O2 and O3ⁱⁱⁱ [symmetry code: (iii) x, y - 1, z] are from two 5-NIP ligands and O7ⁱ, O8 [symmetry code: (i) 1 - x, -y, 1 - z] are from one oxalate ligand. The H13A/O13/H13B water molecule has a fractional site occupancy of 0.50. The ligand 5-NIP chelates the Y(III) ion via its O1/C1/O2 carboxylate group, while its another O3/C8/O4 carboxylate group coordinates to a symmetry related Y(III) ion in monodentate fashion via the atom O3. The O5/N1/O6 nitro group is almost coplanar with the phenyl ring (C2/C3/C4/C5/C6/C7). The O1/C1/O2 carboxylate group is slightly twisted from the phenyl ring with the dihedral angel of 10.26 (41)° based on the phenyl (C2/C3/C4/C5/C6/C7) and the carboxyl (O1/C1/O2) planes. The O3/C8/O4 carboxylate group is out of the phenyl plane with the dihedral angel of 44.41 (36)° based on the phenyl (C2/C3/C4/C5/C6/C7) and the carboxyl (O3/C8/O4) planes. Both two carboxylate groups of the oxalate ligand bridge two symmetry related Y(III) ions in η¹:η¹:µ₂ mode. The oxalate is almost perpendicular to the phenyl plane of 5-NIP with the dihedral angel of 87.42 (26)° based on the phenyl (C2/C3/C4/C5/C6/C7) and the oxalate (O7/C9/O8/C9ⁱ/O7ⁱ/O8ⁱ) [symmetry code: (i) 1 - x, -y, 1 - z] planes. The bond distance of two sp² C9—C9ⁱ [symmetry code: (i) 1 - x, -y, 1 - z] in oxalate is elongated similar with other coordination compounds containing oxalate (Thomas et al., 2002; Nordell et al., 2003). Thus, the ligands 5-NIP link the neighbouring Y(III) ions in the head-to-tail mode to construct an infinite zigzag chain which runs along the b axis direction. Two adjacent zigzag chains are connected via oxalate bridging in the c axis direction to form a ladder-like structure with a grid of 9.207 (11)Å × 6.138 (17)Å based on the intra-ladder intervals of Yttrium (III) ions.

(Burrows et al., 2003; Tang et al., 2006; Kongshaug & Fjellvag, 2006).

All ladders are assembled together through a number of hydrogen bonding (Table 2) between 5-NIP carboxyl O atoms (O1, O2 and O4), nitro O atoms (O5 and O6), oxalate O7 atom and coordination water O atoms (O9, O10 and O11) as well as lattice water molecules (O12 and O13). Among them, H10A and H11B atoms are involved in a three-centered hydrogen bond, respectively. Moreover, the center-center distance between two adjacent phenyl rings of the different ladders is 3.819 (9) Å. It indicates the presence of π-π staking between two adjacent inter-ladder 5-NIP (Janiak et al., 2000). Therefore all ladders are packing via hydrogen bonding and the π-π interactions in the crystal.

Related literature top

For general background, see: Biradha (2003); Braga et al. (2005); Burrows et al. (2003); Kongshaug & Fjellvag (2006); Moulton & Zaworotko (2001); Ohmori et al. (2004); Tang et al. (2006); Janiak (2003). For related structures, see: Thomas et al. (2002); Nordell et al. (2003); Janiak (2000).

For related literature, see: Ren et al. (2006); Si et al. (2004).

Experimental top

Y₂O₃ (22.5 mg, 0.10 mmol), 5-nitro-isophthalic acid (42.2 mg, 0.20 mmol) and Na₂C₂O₄ (26.8 mg, 0.20 mmol) were dissolved in 13 ml water. The mixture was placed in a Teflon-lined stainless steel vessel (25 ml). The vessel was sealed and heated at 443 K for 1 week, then cooled to room temperature. Colorless block crystals were collected by filtration, followed by washing with water and ethanol in 45% yield (38.5 mg). The crystals becam opaque when exposed for a long time in air.

Structure description top

(Burrows et al., 2003; Tang et al., 2006; Kongshaug & Fjellvag, 2006).

For general background, see: Biradha (2003); Braga et al. (2005); Burrows et al. (2003); Kongshaug & Fjellvag (2006); Moulton & Zaworotko (2001); Ohmori et al. (2004); Tang et al. (2006); Janiak (2003). For related structures, see: Thomas et al. (2002); Nordell et al. (2003); Janiak (2000).

For related literature, see: Ren et al. (2006); Si et al. (2004).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), a drawing of the asymmetric unit (solid line portion) with displacement ellipsoids at the 30% probability level, H Atoms have been omitted for clarity [symmetry code: (i) 1 - x, -y, 1 - z; (iii) x, y - 1, z].
	Fig. 2. Two adjacent zigzag chains connected via oxalate bridging to generate a ladder-like structure with a grid of 9.207 (11)Å × 6.138 (17) Å. All hydrogen atoms and the lattice water molecules have been omitted for clarity.
	Fig. 3. A packing diagram of the title compound viewed down the c axis. All hydrogen atoms have been omitted for clarity.

poly[[hexaaquabis(µ-5-nitrobenzene-1,3-dicarboxylato-κ³O,O',O'')(µ- oxalato-κ⁴O,O':O'',O''')diyttrium(III)] trihydrate] top

Crystal data top

[Y₂(C₈H₃NO₆)₂(C₂O₄)(H₂O)₆]·3H₂O	Z = 1
M_r = 846.21	F(000) = 424
Triclinic, P1	D_x = 1.961 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4270 (15) Å	Cell parameters from 25 reflections
b = 9.2070 (18) Å	θ = 2.3–15.0°
c = 11.522 (2) Å	µ = 4.14 mm⁻¹
α = 74.16 (3)°	T = 298 K
β = 71.76 (3)°	Block, colorless
γ = 80.01 (2)°	0.20 × 0.15 × 0.12 mm
V = 716.5 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2260 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.097
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = −11→11
T_min = 0.48, T_max = 0.60	l = −13→14
3018 measured reflections	3 standard reflections every 200 reflections
2785 independent reflections	intensity decay: 1.0%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0432P)² + 2.6078P] where P = (F_o² + 2F_c²)/3
2785 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[Y₂(C₈H₃NO₆)₂(C₂O₄)(H₂O)₆]·3H₂O	γ = 80.01 (2)°
M_r = 846.21	V = 716.5 (3) Å³
Triclinic, P1	Z = 1
a = 7.4270 (15) Å	Mo Kα radiation
b = 9.2070 (18) Å	µ = 4.14 mm⁻¹
c = 11.522 (2) Å	T = 298 K
α = 74.16 (3)°	0.20 × 0.15 × 0.12 mm
β = 71.76 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2260 reflections with I > 2σ(I)
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	R_int = 0.097
T_min = 0.48, T_max = 0.60	3 standard reflections every 200 reflections
3018 measured reflections	intensity decay: 1.0%
2785 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	Δρ_max = 0.67 e Å⁻³
2785 reflections	Δρ_min = −0.64 e Å⁻³
220 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	Occ. (<1)
C1	0.3395 (7)	0.2400 (6)	0.1373 (5)	0.0176 (10)
C2	0.2913 (7)	0.3978 (6)	0.0685 (5)	0.0182 (10)
C3	0.2644 (7)	0.4243 (6)	−0.0506 (5)	0.0200 (11)
H3	0.2853	0.3461	−0.0909	0.024*
C4	0.2095 (7)	0.5698 (6)	−0.1067 (5)	0.0188 (10)
C5	0.1769 (7)	0.6925 (6)	−0.0509 (5)	0.0187 (10)
H5	0.1321	0.7878	−0.0904	0.022*
C6	0.2101 (7)	0.6653 (6)	0.0648 (5)	0.0181 (10)
C7	0.2687 (7)	0.5187 (6)	0.1238 (5)	0.0201 (11)
H7	0.2862	0.4994	0.2030	0.024*
C8	0.1873 (7)	0.7916 (6)	0.1298 (5)	0.0187 (10)
C9	0.6051 (7)	−0.0058 (6)	0.4632 (5)	0.0177 (10)
N1	0.1769 (7)	0.5962 (5)	−0.2319 (4)	0.0265 (10)
O1	0.3821 (6)	0.2183 (4)	0.2395 (3)	0.0261 (9)
O2	0.3332 (5)	0.1288 (4)	0.0962 (3)	0.0228 (8)
O3	0.3182 (5)	0.7902 (4)	0.1793 (3)	0.0223 (8)
O4	0.0460 (5)	0.8849 (4)	0.1325 (4)	0.0251 (8)
O5	0.1269 (9)	0.7245 (5)	−0.2819 (5)	0.0564 (15)
O6	0.1979 (8)	0.4894 (5)	−0.2778 (4)	0.0461 (12)
O7	0.7221 (5)	0.0136 (4)	0.5150 (3)	0.0214 (8)
O8	0.6444 (5)	−0.0325 (4)	0.3571 (3)	0.0232 (8)
O9	0.6774 (5)	−0.0796 (4)	0.1250 (3)	0.0244 (8)
H9A	0.6641	−0.0316	0.0534	0.029*
H9B	0.7642	−0.0428	0.1386	0.029*
O10	0.4350 (6)	−0.3006 (4)	0.3988 (4)	0.0326 (10)
H10A	0.5526	−0.3322	0.3807	0.039*
H10B	0.3968	−0.3009	0.4765	0.039*
O11	0.0652 (5)	−0.0383 (5)	0.3376 (4)	0.0318 (10)
H11B	0.0191	0.0193	0.3884	0.038*
H11A	0.0252	−0.0036	0.2728	0.038*
O12	0.3768 (8)	0.3842 (5)	0.4156 (5)	0.0492 (13)
H12B	0.3942	0.4764	0.3793	0.059*
H12A	0.4299	0.3285	0.3639	0.059*
O13	0.0067 (15)	0.3583 (14)	0.5020 (11)	0.068 (3)	0.50
H13A	0.0037	0.2670	0.5003	0.081*	0.50
H13B	−0.1035	0.3933	0.5392	0.081*	0.50
Y	0.39399 (7)	−0.05405 (6)	0.27921 (5)	0.01386 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.018 (2)	0.018 (3)	0.017 (2)	−0.0018 (19)	−0.005 (2)	−0.004 (2)
C2	0.019 (3)	0.017 (3)	0.019 (3)	−0.002 (2)	−0.005 (2)	−0.005 (2)
C3	0.020 (3)	0.020 (3)	0.022 (3)	−0.002 (2)	−0.007 (2)	−0.008 (2)
C4	0.020 (3)	0.024 (3)	0.015 (2)	−0.004 (2)	−0.004 (2)	−0.007 (2)
C5	0.024 (3)	0.012 (2)	0.022 (3)	−0.002 (2)	−0.011 (2)	−0.002 (2)
C6	0.021 (3)	0.018 (3)	0.020 (3)	−0.004 (2)	−0.009 (2)	−0.006 (2)
C7	0.022 (3)	0.021 (3)	0.020 (3)	−0.002 (2)	−0.009 (2)	−0.005 (2)
C8	0.017 (2)	0.020 (3)	0.018 (2)	−0.004 (2)	−0.002 (2)	−0.006 (2)
C9	0.018 (3)	0.016 (3)	0.019 (3)	−0.0011 (19)	−0.006 (2)	−0.003 (2)
N1	0.034 (3)	0.027 (3)	0.021 (2)	−0.004 (2)	−0.013 (2)	−0.004 (2)
O1	0.044 (2)	0.0195 (19)	0.0213 (19)	−0.0005 (17)	−0.0204 (17)	−0.0047 (15)
O2	0.037 (2)	0.0142 (18)	0.0217 (19)	−0.0004 (15)	−0.0135 (16)	−0.0062 (15)
O3	0.0254 (19)	0.0190 (19)	0.033 (2)	0.0032 (15)	−0.0188 (17)	−0.0132 (16)
O4	0.0216 (19)	0.025 (2)	0.036 (2)	0.0056 (15)	−0.0149 (17)	−0.0160 (17)
O5	0.113 (5)	0.028 (3)	0.036 (3)	0.007 (3)	−0.046 (3)	0.000 (2)
O6	0.078 (4)	0.038 (3)	0.034 (2)	0.007 (2)	−0.029 (2)	−0.020 (2)
O7	0.0161 (17)	0.036 (2)	0.0171 (18)	−0.0056 (15)	−0.0082 (14)	−0.0089 (16)
O8	0.0213 (19)	0.037 (2)	0.0159 (18)	−0.0030 (16)	−0.0066 (15)	−0.0118 (16)
O9	0.0205 (19)	0.039 (2)	0.0171 (18)	−0.0029 (16)	−0.0058 (15)	−0.0124 (16)
O10	0.046 (3)	0.028 (2)	0.028 (2)	0.0010 (19)	−0.0182 (19)	−0.0061 (17)
O11	0.0196 (19)	0.057 (3)	0.028 (2)	0.0038 (18)	−0.0103 (16)	−0.027 (2)
O12	0.079 (4)	0.036 (3)	0.044 (3)	−0.008 (2)	−0.033 (3)	−0.008 (2)
O13	0.045 (6)	0.075 (8)	0.074 (8)	−0.031 (6)	−0.011 (6)	0.006 (6)
Y	0.0155 (2)	0.0154 (2)	0.0136 (2)	−0.00013 (16)	−0.00695 (17)	−0.00552 (17)

Geometric parameters (Å, º) top

C1—O2	1.253 (6)	N1—O6	1.204 (6)
C1—O1	1.269 (6)	N1—O5	1.215 (6)
C1—C2	1.495 (7)	O1—Y	2.414 (4)
C1—Y	2.790 (5)	O2—Y	2.424 (4)
C2—C7	1.388 (7)	O3—Yⁱⁱ	2.299 (3)
C2—C3	1.398 (7)	O7—Yⁱ	2.365 (3)
C3—C4	1.372 (7)	O8—Y	2.361 (3)
C3—H3	0.9264	O9—Y	2.314 (4)
C4—C5	1.397 (7)	O9—H9A	0.8500
C4—N1	1.484 (7)	O9—H9B	0.8501
C5—C6	1.380 (7)	O10—Y	2.336 (4)
C5—H5	0.9288	O10—H10A	0.8500
C6—C7	1.398 (7)	O10—H10B	0.8501
C6—C8	1.507 (7)	O11—Y	2.311 (4)
C7—H7	0.9274	O11—H11B	0.8500
C8—O4	1.233 (6)	O11—H11A	0.8498
C8—O3	1.268 (6)	O12—H12B	0.8499
C9—O8	1.247 (6)	O12—H12A	0.8500
C9—O7	1.258 (6)	O13—H13A	0.8500
C9—C9ⁱ	1.527 (9)	O13—H13B	0.8500

O2—C1—O1	119.8 (5)	H10A—O10—H10B	108.3
O2—C1—C2	120.3 (4)	Y—O11—H11B	110.1
O1—C1—C2	119.9 (4)	Y—O11—H11A	109.8
O2—C1—Y	60.2 (3)	H11B—O11—H11A	109.8
O1—C1—Y	59.8 (3)	H12B—O12—H12A	109.7
C2—C1—Y	174.6 (3)	H13A—O13—H13B	109.5
C7—C2—C3	119.5 (5)	O3ⁱⁱⁱ—Y—O11	74.28 (13)
C7—C2—C1	120.2 (4)	O3ⁱⁱⁱ—Y—O9	78.95 (13)
C3—C2—C1	120.3 (4)	O11—Y—O9	147.86 (13)
C4—C3—C2	118.1 (5)	O3ⁱⁱⁱ—Y—O10	74.18 (13)
C4—C3—H3	121.0	O11—Y—O10	95.62 (16)
C2—C3—H3	120.8	O9—Y—O10	93.86 (15)
C3—C4—C5	123.7 (5)	O3ⁱⁱⁱ—Y—O8	138.88 (13)
C3—C4—N1	117.7 (4)	O11—Y—O8	139.85 (13)
C5—C4—N1	118.6 (4)	O9—Y—O8	72.16 (12)
C6—C5—C4	117.4 (5)	O10—Y—O8	79.18 (14)
C6—C5—H5	122.0	O3ⁱⁱⁱ—Y—O7ⁱ	133.63 (13)
C4—C5—H5	120.5	O11—Y—O7ⁱ	71.41 (12)
C5—C6—C7	120.3 (5)	O9—Y—O7ⁱ	140.67 (12)
C5—C6—C8	121.3 (5)	O10—Y—O7ⁱ	79.12 (14)
C7—C6—C8	118.4 (4)	O8—Y—O7ⁱ	68.51 (12)
C2—C7—C6	120.9 (5)	O3ⁱⁱⁱ—Y—O1	132.35 (12)
C2—C7—H7	118.6	O11—Y—O1	90.19 (15)
C6—C7—H7	120.4	O9—Y—O1	94.96 (14)
O4—C8—O3	125.6 (5)	O10—Y—O1	153.26 (13)
O4—C8—C6	119.0 (4)	O8—Y—O1	79.61 (13)
O3—C8—C6	115.4 (4)	O7ⁱ—Y—O1	78.08 (13)
O8—C9—O7	126.2 (4)	O3ⁱⁱⁱ—Y—O2	79.18 (12)
O8—C9—C9ⁱ	117.0 (5)	O11—Y—O2	80.27 (14)
O7—C9—C9ⁱ	116.8 (5)	O9—Y—O2	77.50 (13)
O6—N1—O5	123.2 (5)	O10—Y—O2	153.13 (13)
O6—N1—C4	118.6 (5)	O8—Y—O2	120.73 (13)
O5—N1—C4	118.2 (5)	O7ⁱ—Y—O2	123.38 (13)
C1—O1—Y	93.2 (3)	O1—Y—O2	53.60 (12)
C1—O2—Y	93.2 (3)	O3ⁱⁱⁱ—Y—C1	105.48 (14)
C8—O3—Yⁱⁱ	136.0 (3)	O11—Y—C1	83.57 (15)
C9—O7—Yⁱ	118.6 (3)	O9—Y—C1	86.78 (14)
C9—O8—Y	119.0 (3)	O10—Y—C1	179.19 (14)
Y—O9—H9A	109.9	O8—Y—C1	101.50 (14)
Y—O9—H9B	109.8	O7ⁱ—Y—C1	100.69 (14)
H9A—O9—H9B	108.4	O1—Y—C1	27.01 (13)
Y—O10—H10A	109.3	O2—Y—C1	26.64 (13)
Y—O10—H10B	109.8

O2—C1—C2—C7	169.7 (5)	C9—O8—Y—O3ⁱⁱⁱ	−134.9 (4)
O1—C1—C2—C7	−8.3 (7)	C9—O8—Y—O11	1.1 (5)
O2—C1—C2—C3	−8.9 (7)	C9—O8—Y—O9	177.5 (4)
O1—C1—C2—C3	173.0 (5)	C9—O8—Y—O10	−84.8 (4)
C7—C2—C3—C4	−2.3 (7)	C9—O8—Y—O7ⁱ	−2.3 (4)
C1—C2—C3—C4	176.3 (4)	C9—O8—Y—O1	78.8 (4)
C2—C3—C4—C5	−0.8 (8)	C9—O8—Y—O2	114.6 (4)
C2—C3—C4—N1	−178.6 (4)	C9—O8—Y—C1	94.7 (4)
C3—C4—C5—C6	2.9 (8)	C1—O1—Y—O3ⁱⁱⁱ	−6.7 (4)
N1—C4—C5—C6	−179.3 (4)	C1—O1—Y—O11	−75.3 (3)
C4—C5—C6—C7	−1.8 (7)	C1—O1—Y—O9	72.9 (3)
C4—C5—C6—C8	177.3 (4)	C1—O1—Y—O10	−178.3 (3)
C3—C2—C7—C6	3.3 (8)	C1—O1—Y—O8	143.7 (3)
C1—C2—C7—C6	−175.3 (4)	C1—O1—Y—O7ⁱ	−146.3 (3)
C5—C6—C7—C2	−1.2 (8)	C1—O1—Y—O2	2.4 (3)
C8—C6—C7—C2	179.7 (4)	C1—O2—Y—O3ⁱⁱⁱ	170.8 (3)
C5—C6—C8—O4	44.6 (7)	C1—O2—Y—O11	95.1 (3)
C7—C6—C8—O4	−136.2 (5)	C1—O2—Y—O9	−108.3 (3)
C5—C6—C8—O3	−136.3 (5)	C1—O2—Y—O10	178.3 (3)
C7—C6—C8—O3	42.8 (7)	C1—O2—Y—O8	−48.1 (3)
C3—C4—N1—O6	0.8 (7)	C1—O2—Y—O7ⁱ	35.1 (3)
C5—C4—N1—O6	−177.1 (5)	C1—O2—Y—O1	−2.4 (3)
C3—C4—N1—O5	179.5 (5)	O2—C1—Y—O3ⁱⁱⁱ	−9.4 (3)
C5—C4—N1—O5	1.5 (8)	O1—C1—Y—O3ⁱⁱⁱ	174.9 (3)
O2—C1—O1—Y	−4.3 (5)	O2—C1—Y—O11	−81.1 (3)
C2—C1—O1—Y	173.8 (4)	O1—C1—Y—O11	103.2 (3)
O1—C1—O2—Y	4.3 (5)	O2—C1—Y—O9	68.2 (3)
C2—C1—O2—Y	−173.8 (4)	O1—C1—Y—O9	−107.5 (3)
O4—C8—O3—Yⁱⁱ	−6.0 (8)	O2—C1—Y—O8	139.3 (3)
C6—C8—O3—Yⁱⁱ	175.0 (3)	O1—C1—Y—O8	−36.4 (3)
O8—C9—O7—Yⁱ	−177.9 (4)	O2—C1—Y—O7ⁱ	−150.8 (3)
C9ⁱ—C9—O7—Yⁱ	2.7 (7)	O1—C1—Y—O7ⁱ	33.5 (3)
O7—C9—O8—Y	−177.5 (4)	O2—C1—Y—O1	175.7 (5)
C9ⁱ—C9—O8—Y	1.9 (7)	O1—C1—Y—O2	−175.7 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O2^iv	0.85	2.14	2.735 (5)	127
O9—H9B···O4^v	0.85	2.07	2.726 (5)	134
O10—H10A···O6^iv	0.85	2.36	3.115 (7)	148
O10—H10B···O12ⁱ	0.85	2.30	2.778 (6)	116
O10—H10B···O12ⁱ	0.85	2.30	2.778 (6)	116
O11—H11A···O4ⁱⁱⁱ	0.85	2.09	2.694 (5)	127
O11—H11B···O5^vi	0.85	2.57	2.987 (6)	111
O11—H11B···O7^vii	0.85	2.23	2.784 (5)	123
O12—H12A···O1	0.85	2.11	2.841 (6)	144
O12—H12B···O10ⁱⁱ	0.85	2.21	2.953 (6)	147
C3—H3···O9^iv	0.93	2.54	3.432 (6)	161

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

Experimental details

Crystal data
Chemical formula	[Y₂(C₈H₃NO₆)₂(C₂O₄)(H₂O)₆]·3H₂O
M_r	846.21
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.4270 (15), 9.2070 (18), 11.522 (2)
α, β, γ (°)	74.16 (3), 71.76 (3), 80.01 (2)
V (Å³)	716.5 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	4.14
Crystal size (mm)	0.20 × 0.15 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (XCAD4; Harms & Wocadlo, 1995)
T_min, T_max	0.48, 0.60
No. of measured, independent and observed [I > 2σ(I)] reflections	3018, 2785, 2260
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.112, 1.05
No. of reflections	2785
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.64

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2000), SHELXTL.

Selected bond lengths (Å) top

O1—Y	2.414 (4)	O8—Y	2.361 (3)
O2—Y	2.424 (4)	O9—Y	2.314 (4)
O3—Yⁱ	2.299 (3)	O10—Y	2.336 (4)
O7—Yⁱⁱ	2.365 (3)	O11—Y	2.311 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O2ⁱⁱⁱ	0.85	2.14	2.735 (5)	126.5
O9—H9B···O4^iv	0.85	2.07	2.726 (5)	133.7
O10—H10A···O6ⁱⁱⁱ	0.85	2.36	3.115 (7)	148.3
O10—H10B···O12ⁱⁱ	0.85	2.30	2.778 (6)	115.7
O10—H10B···O12ⁱⁱ	0.85	2.30	2.778 (6)	115.7
O11—H11A···O4^v	0.85	2.09	2.694 (5)	127.2
O11—H11B···O5^vi	0.85	2.57	2.987 (6)	111.3
O11—H11B···O7^vii	0.85	2.23	2.784 (5)	122.7
O12—H12A···O1	0.85	2.11	2.841 (6)	144.0
O12—H12B···O10ⁱ	0.85	2.21	2.953 (6)	146.5

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

Acknowledgements

This work was funded by the Doctoral Research Launch Foundation of Anhui Normal University and the Youth Research Foundation of Anhui Normal University (grant No. 2006xqn64).

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