Poly[[triaqua­(μ3-4-oxidopyridine-2,6-dicarboxyl­ato)europium(III)] monohydrate]

Lv, D.-Y.; Gao, Z.-Q.; Gu, J.-Z.

doi:10.1107/S1600536810048518

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1694-m1695

https://doi.org/10.1107/S1600536810048518

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Poly[[triaqua(μ₃-4-oxidopyridine-2,6-dicarboxylato)europium(III)] monohydrate]

Dong-Yu Lv,^a ^* Zhu-Qing Gao ^b and Jin-Zhong Gu ^a

^aKey Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China, and ^bSchool of Chemistry and Biology Engineering, Taiyuan University of Science and Technology, Taiyuan 030021, People's Republic of China
^*Correspondence e-mail: lvdy@lzu.edu.cn

(Received 11 November 2010; accepted 21 November 2010; online 30 November 2010)

In the title coordination polymer, {[Eu(C₇H₂NO₅)(H₂O)₃]·H₂O}_n, the Eu^III atom is eight-coordinated by a tridentate 4-oxidopyridine-2,6-dicarboxylate (hpc) trianion, two monodentate hpc anions and three water molecules, forming a distorted bicapped trigonal–prismatic coordination geometry. The hpc ligands bridge adjacent Eu^III ions, forming infinite double chains. Adjacent chains are further connected by hpc ligands into sheets. O—H⋯O hydrogen bonds then generate a three-dimensional supramolecular framework.

Related literature

For the structures and properties of lanthanide coordination compounds, see: He et al. (2010 ); Kustaryono et al. (2010 ); Zhu, Sun et al. (2009 ); Wong et al. (2006 ). For the use of multi-carboxylate and heterocyclic acids in coordination chemistry, see: Li et al. (2008 ); Luo et al. (2008 ) and for the dicarboxylate ligand H₃CAM (H₃CAM is 4-hydroxy-pyridine-2,6-dicarboxylic acid), see: Gao et al. (2006 , 2008 ). For the isotypic structure {[Dy(CAM)(H₂O)₃]·H₂O}_n, see: Gao et al. (2006). For bond lengths and angles in other complexes with eight-coordinate Eu^III, see: Li et al. (2008); Zhu, Ikarashi et al. (2009 )

Experimental

Crystal data

[Eu(C₇H₂NO₅)(H₂O)₃]·H₂O
M_r = 404.12
Monoclinic, P 2₁ /n
a = 10.0041 (15) Å
b = 7.5456 (11) Å
c = 15.528 (2) Å
β = 104.890 (1)°
V = 1132.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 5.58 mm⁻¹
T = 296 K
0.35 × 0.32 × 0.31 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.246, T_max = 0.277
4884 measured reflections
2023 independent reflections
1856 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.065
S = 1.06
2023 reflections
196 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.82 e Å⁻³
Δρ_min = −1.69 e Å⁻³

Table 1
Selected bond lengths (Å)

Eu1—O5ⁱ	2.327 (2)
Eu1—O8	2.401 (3)
Eu1—O7	2.416 (3)
Eu1—O1	2.432 (2)
Eu1—O2ⁱⁱ	2.433 (2)
Eu1—O3	2.440 (2)
Eu1—O6	2.445 (3)
Eu1—N1	2.498 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H1W⋯O9ⁱⁱⁱ	0.90 (2)	1.85 (3)	2.696 (3)	158 (4)
O6—H2W⋯O9^iv	0.87 (2)	2.15 (3)	2.962 (4)	156 (4)
O7—H4W⋯O3ⁱⁱⁱ	0.86 (2)	2.09 (3)	2.805 (3)	141 (4)
O8—H5W⋯O1ⁱⁱ	0.86 (2)	1.84 (2)	2.684 (4)	168 (4)
O8—H6W⋯O4^v	0.87 (2)	1.83 (2)	2.696 (4)	173 (4)
O9—H7W⋯O2^vi	0.86 (2)	2.26 (3)	3.059 (4)	155 (5)
O9—H8W⋯O4	0.86 (2)	1.84 (2)	2.692 (4)	172 (6)
Symmetry codes: (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) -x+1, -y+2, -z+2; (vi) x-1, y, z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048518/hb5735sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048518/hb5735Isup2.hkl

checkCIF report

Comment top

The design and synthesis of lanthanide coordination polymers have achieved great progress over the past decades(He et al., 2010; Kustaryono et al., 2010). These coordination polymers have shown not only their versatile architectures but also their desirable properties luminescent, magnetic, catalytic, and gas absorption and separation properties (Zhu et al., 2009; Wong et al., 2006). Many multi-carboxylate or heterocylic carboxylic acids are used for this purpose (Li et al., 2008; Luo et al., 2008). In the designed synthesis of the lanthanide coordination polymers, 4-hydroxy-pyridine-2,6-dicarboxylic acid (H₃CAM) is an excellent pyridine dicarboxylate ligand (Gao et al., 2006; Gao et al., 2008),which can afford at most one nitrogen atom and five O coordination sites. In order to extend the investigation in this field, we designed and synthesized one lanthanidecoordination polymer [Eu(CAM)(H₂O)₃]_n.nH₂O, and report its structure here.

The title compound is located on a twofold helical axis of symmetry, which is isomorphous with {[Dy(CAM)(H₂O)₃].H₂O}_n (Gao et al., 2006). As shown in Fig.1, the asymmetrical unit of the cell contains one Eu (III) ion, one CAM liangd, three coordinated water molecules, and one guest water molecule. Eu atom is eight-coordinated with seven oxygen atoms from three individual CAM ligands and three coordinated water molecules and one nitrogen atom from the CAM ligand, forming a distorted bicapped square-prismatic coordination geometry.

Important bond distances and angles are presented in Table 1. The Eu–O bond distances [2.327 (2) to 2.445 (3) Å]are shorter than the Eu–N bond distance [2.498 (3) Å], which are in good with those observed in other Eu (III) complexes (Li et al., 2008; Zhu et al., 2009). The CAM ligands adopt a µ₃-pentadentate coordination mode, as shown in Fig.1. The CAM ligands bridge the adjacent Eu^III ions to form infinite double chains (Fig.2). The adjacent chains are further connected by the coordination of the CAMligands and Eu^III ions to form two-dimensional sheet (Fig.3), which are further extended into three-dimensional supramolecular frameworks through H-bond interactions (Table 4).

Related literature top

For the structures and properties of lanthanide coordination compounds, see: He et al. (2010); Kustaryono et al. (2010); Zhu, Sun et al. (2009); Wong et al. (2006). For the use of multi-carboxylate and heterocyclic acids in coordination chemistry, see: Li et al. (2008); Luo et al. (2008) and for the dicarboxylate ligand H₃CAM (H₃CAM is 4-hydroxy-pyridine-2,6-dicarboxylic acid), see: Gao et al. (2006, 2008). For the isotypic structure {[Dy(CAM)(H₂O)₃].H₂O}_n, see: Gao et al. (2006). For bond distances and angles in other eight-coordinated Eu ^IIIcomplexes, see: Li et al. (2008); Zhu, Ikarashi et al. (2009).

Experimental top

To a solution of europium nitrate hexahydrate (0.134 g, 0.3 mmol) in water (5 ml) was added an aqueous solution (5 ml) of the ligand (0.060 g, 0.3 mmol) and a drop of triethylamine. The reactants were sealed in a 25-ml Teflon-lined, stainless-steel Parr bomb. The bomb was heated at 433 K for 3 days. The cool solution yielded colourless blocks in ca 60% yield. Anal. Calcd for C₇H₁₀EuNO₉: C, 20.80; H, 2.49; N, 3.47. Found: C, 20.51; H, 2.77; N, 3.12.

Structure description top

For the structures and properties of lanthanide coordination compounds, see: He et al. (2010); Kustaryono et al. (2010); Zhu, Sun et al. (2009); Wong et al. (2006). For the use of multi-carboxylate and heterocyclic acids in coordination chemistry, see: Li et al. (2008); Luo et al. (2008) and for the dicarboxylate ligand H₃CAM (H₃CAM is 4-hydroxy-pyridine-2,6-dicarboxylic acid), see: Gao et al. (2006, 2008). For the isotypic structure {[Dy(CAM)(H₂O)₃].H₂O}_n, see: Gao et al. (2006). For bond distances and angles in other eight-coordinated Eu ^IIIcomplexes, see: Li et al. (2008); Zhu, Ikarashi et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A drawing of the asymmetric unit in the structure of (I), showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A view along the b axis, showing a one-dimensional double chain of [Eu(CAM)(H₂O)₃].
	Fig. 3. A view along the a axis, showing a two-dimensional sheet of [Eu(CAM)(H₂O)₃].

Poly[[triaqua(µ₃-4-oxidopyridine-2,6-dicarboxylato)europium(III)] monohydrate] top

Crystal data top

[Eu(C₇H₂NO₅)(H₂O)₃]·H₂O	F(000) = 776
M_r = 404.12	D_x = 2.370 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3455 reflections
a = 10.0041 (15) Å	θ = 2.8–28.3°
b = 7.5456 (11) Å	µ = 5.58 mm⁻¹
c = 15.528 (2) Å	T = 296 K
β = 104.890 (1)°	Block, colorless
V = 1132.8 (3) Å³	0.35 × 0.32 × 0.31 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2023 independent reflections
Radiation source: fine-focus sealed tube	1856 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
φ and ω scans	θ_max = 25.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→12
T_min = 0.246, T_max = 0.277	k = −9→7
4884 measured reflections	l = −14→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.065	w = 1/[σ²(F_o²) + 0.5803P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2023 reflections	Δρ_max = 0.82 e Å⁻³
196 parameters	Δρ_min = −1.69 e Å⁻³
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0273 (8)

Crystal data top

[Eu(C₇H₂NO₅)(H₂O)₃]·H₂O	V = 1132.8 (3) Å³
M_r = 404.12	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0041 (15) Å	µ = 5.58 mm⁻¹
b = 7.5456 (11) Å	T = 296 K
c = 15.528 (2) Å	0.35 × 0.32 × 0.31 mm
β = 104.890 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2023 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1856 reflections with I > 2σ(I)
T_min = 0.246, T_max = 0.277	R_int = 0.074
4884 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	12 restraints
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.82 e Å⁻³
2023 reflections	Δρ_min = −1.69 e Å⁻³
196 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
Eu1	0.500412 (13)	0.82415 (2)	0.746168 (10)	0.01204 (13)
C1	0.7849 (3)	0.5972 (4)	0.8389 (2)	0.0179 (7)
C2	0.7266 (3)	0.6188 (4)	0.9168 (2)	0.0159 (7)
C3	0.7942 (3)	0.5648 (4)	1.0015 (2)	0.0168 (7)
H3	0.8789	0.5069	1.0112	0.020*
H5	0.5632	0.7067	1.0980	0.020*
C4	0.7362 (3)	0.5967 (4)	1.0731 (2)	0.0153 (7)
C5	0.6069 (3)	0.6829 (4)	1.0528 (2)	0.0164 (8)
C6	0.5456 (3)	0.7327 (4)	0.9664 (2)	0.0142 (7)
C7	0.4087 (3)	0.8280 (4)	0.9380 (2)	0.0163 (8)
H1W	0.492 (5)	0.543 (3)	0.609 (3)	0.073 (17)*
H2W	0.536 (5)	0.692 (5)	0.567 (3)	0.060 (17)*
H3W	0.327 (5)	0.552 (7)	0.785 (2)	0.08 (2)*
H4W	0.315 (4)	0.511 (6)	0.6919 (18)	0.071 (17)*
H5W	0.660 (4)	1.125 (6)	0.802 (2)	0.069 (17)*
H6W	0.623 (4)	1.093 (6)	0.8862 (12)	0.047 (13)*
H7W	0.034 (5)	0.735 (6)	0.899 (4)	0.11 (2)*
H8W	0.155 (2)	0.835 (6)	0.949 (4)	0.078 (19)*
N1	0.6033 (3)	0.7025 (3)	0.89845 (18)	0.0151 (6)
O1	0.7227 (3)	0.6764 (3)	0.76842 (16)	0.0270 (7)
O2	0.8922 (2)	0.5058 (3)	0.84687 (15)	0.0234 (6)
O3	0.3689 (2)	0.8704 (3)	0.85661 (15)	0.0211 (5)
O4	0.3426 (2)	0.8572 (3)	0.99465 (16)	0.0245 (6)
O5	0.8011 (2)	0.5511 (3)	1.15508 (14)	0.0202 (5)
O6	0.5004 (3)	0.6614 (3)	0.61007 (18)	0.0275 (6)
O7	0.3631 (3)	0.5587 (4)	0.73985 (19)	0.0323 (7)
O8	0.6026 (3)	1.0809 (4)	0.82870 (18)	0.0319 (7)
O9	0.0664 (3)	0.8216 (3)	0.9349 (2)	0.0367 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.01379 (17)	0.01728 (17)	0.00543 (16)	0.00006 (5)	0.00313 (11)	0.00080 (5)
C1	0.0194 (16)	0.0240 (17)	0.0107 (17)	0.0022 (14)	0.0047 (14)	−0.0012 (14)
C2	0.0192 (16)	0.0166 (16)	0.0130 (17)	0.0000 (13)	0.0060 (14)	0.0001 (14)
C3	0.0189 (16)	0.0193 (16)	0.0119 (16)	0.0030 (13)	0.0031 (14)	0.0014 (13)
C4	0.0194 (15)	0.0171 (16)	0.0079 (16)	−0.0042 (13)	0.0010 (13)	0.0026 (13)
C5	0.0186 (17)	0.0243 (18)	0.0094 (17)	−0.0032 (12)	0.0092 (14)	−0.0015 (13)
C6	0.0195 (17)	0.0153 (15)	0.0094 (16)	−0.0007 (13)	0.0068 (14)	−0.0007 (13)
C7	0.0180 (17)	0.0193 (17)	0.0109 (18)	−0.0021 (13)	0.0028 (15)	−0.0021 (13)
N1	0.0175 (14)	0.0206 (13)	0.0071 (14)	0.0027 (11)	0.0033 (12)	0.0021 (11)
O1	0.0276 (14)	0.0468 (17)	0.0090 (13)	0.0166 (11)	0.0092 (11)	0.0085 (11)
O2	0.0241 (13)	0.0330 (14)	0.0128 (12)	0.0135 (11)	0.0043 (10)	−0.0014 (11)
O3	0.0201 (11)	0.0338 (13)	0.0094 (12)	0.0077 (11)	0.0041 (10)	0.0031 (11)
O4	0.0236 (12)	0.0419 (15)	0.0110 (13)	0.0061 (11)	0.0097 (11)	−0.0009 (11)
O5	0.0206 (11)	0.0305 (13)	0.0087 (12)	−0.0030 (10)	0.0021 (10)	0.0042 (10)
O6	0.0423 (17)	0.0266 (15)	0.0169 (15)	−0.0036 (12)	0.0135 (14)	−0.0033 (11)
O7	0.0413 (16)	0.0376 (16)	0.0212 (15)	−0.0181 (13)	0.0141 (14)	−0.0058 (13)
O8	0.0451 (16)	0.0393 (16)	0.0164 (14)	−0.0194 (14)	0.0172 (13)	−0.0085 (12)
O9	0.0278 (16)	0.0311 (16)	0.049 (2)	0.0034 (12)	0.0062 (15)	0.0025 (13)

Geometric parameters (Å, º) top

Eu1—O5ⁱ	2.327 (2)	C5—C6	1.377 (4)
Eu1—O8	2.401 (3)	C5—H5	0.9344
Eu1—O7	2.416 (3)	C6—N1	1.345 (4)
Eu1—O1	2.432 (2)	C6—C7	1.509 (4)
Eu1—O2ⁱⁱ	2.433 (2)	C7—O4	1.249 (4)
Eu1—O3	2.440 (2)	C7—O3	1.264 (4)
Eu1—O6	2.445 (3)	O2—Eu1ⁱⁱⁱ	2.433 (2)
Eu1—N1	2.498 (3)	O5—Eu1^iv	2.327 (2)
C1—O2	1.255 (4)	O6—H1W	0.895 (19)
C1—O1	1.262 (4)	O6—H2W	0.867 (19)
C1—C2	1.481 (5)	O7—H3W	0.871 (19)
C2—N1	1.350 (4)	O7—H4W	0.856 (19)
C2—C3	1.376 (4)	O8—H5W	0.855 (19)
C3—C4	1.402 (5)	O8—H6W	0.868 (18)
C3—H3	0.9300	O9—H7W	0.861 (19)
C4—O5	1.317 (3)	O9—H8W	0.861 (19)
C4—C5	1.410 (4)

O5ⁱ—Eu1—O8	100.29 (9)	O2—C1—C2	119.1 (3)
O5ⁱ—Eu1—O7	85.49 (9)	O1—C1—C2	116.5 (3)
O8—Eu1—O7	148.21 (10)	N1—C2—C3	122.6 (3)
O5ⁱ—Eu1—O1	151.83 (8)	N1—C2—C1	114.1 (3)
O8—Eu1—O1	92.61 (9)	C3—C2—C1	123.2 (3)
O7—Eu1—O1	96.63 (9)	C2—C3—C4	120.4 (3)
O5ⁱ—Eu1—O2ⁱⁱ	81.44 (8)	C2—C3—H3	119.8
O8—Eu1—O2ⁱⁱ	70.73 (9)	C4—C3—H3	119.8
O7—Eu1—O2ⁱⁱ	140.91 (9)	O5—C4—C3	121.4 (3)
O1—Eu1—O2ⁱⁱ	79.36 (8)	O5—C4—C5	122.2 (3)
O5ⁱ—Eu1—O3	80.61 (8)	C3—C4—C5	116.4 (3)
O8—Eu1—O3	75.04 (9)	C6—C5—C4	119.8 (3)
O7—Eu1—O3	75.15 (9)	C6—C5—H5	120.2
O1—Eu1—O3	127.18 (8)	C4—C5—H5	120.0
O2ⁱⁱ—Eu1—O3	137.46 (8)	N1—C6—C5	123.0 (3)
O5ⁱ—Eu1—O6	82.43 (9)	N1—C6—C7	113.1 (3)
O8—Eu1—O6	140.55 (10)	C5—C6—C7	123.9 (3)
O7—Eu1—O6	71.01 (10)	O4—C7—O3	124.9 (3)
O1—Eu1—O6	71.90 (9)	O4—C7—C6	118.9 (3)
O2ⁱⁱ—Eu1—O6	70.83 (9)	O3—C7—C6	116.2 (3)
O3—Eu1—O6	143.08 (9)	C6—N1—C2	117.8 (3)
O5ⁱ—Eu1—N1	143.53 (9)	C6—N1—Eu1	121.6 (2)
O8—Eu1—N1	77.05 (9)	C2—N1—Eu1	120.3 (2)
O7—Eu1—N1	79.95 (9)	C1—O1—Eu1	124.7 (2)
O1—Eu1—N1	63.77 (9)	C1—O2—Eu1ⁱⁱⁱ	138.4 (2)
O2ⁱⁱ—Eu1—N1	129.18 (9)	C7—O3—Eu1	125.3 (2)
O3—Eu1—N1	63.42 (8)	C4—O5—Eu1^iv	127.88 (19)
O6—Eu1—N1	122.83 (9)	Eu1—O6—H1W	119 (3)
O5ⁱ—Eu1—H5W	101.3 (10)	Eu1—O6—H2W	129 (3)
O8—Eu1—H5W	17.0 (6)	H1W—O6—H2W	108 (3)
O7—Eu1—H5W	164.4 (6)	Eu1—O7—H3W	111 (3)
O1—Eu1—H5W	84.1 (10)	Eu1—O7—H4W	125 (3)
O2ⁱⁱ—Eu1—H5W	54.6 (6)	H3W—O7—H4W	115 (3)
O3—Eu1—H5W	91.9 (6)	Eu1—O8—H5W	108 (3)
O6—Eu1—H5W	123.6 (6)	Eu1—O8—H6W	126 (3)
N1—Eu1—H5W	86.4 (8)	H5W—O8—H6W	116 (3)
O2—C1—O1	124.4 (3)	H7W—O9—H8W	116 (3)

O2—C1—C2—N1	−173.0 (3)	O6—Eu1—N1—C6	−143.3 (2)
O1—C1—C2—N1	8.2 (4)	O5ⁱ—Eu1—N1—C2	170.8 (2)
O2—C1—C2—C3	9.4 (5)	O8—Eu1—N1—C2	−99.4 (2)
O1—C1—C2—C3	−169.3 (3)	O7—Eu1—N1—C2	102.7 (2)
N1—C2—C3—C4	−0.4 (5)	O1—Eu1—N1—C2	0.1 (2)
C1—C2—C3—C4	177.0 (3)	O2ⁱⁱ—Eu1—N1—C2	−48.0 (3)
C2—C3—C4—O5	−177.9 (3)	O3—Eu1—N1—C2	−178.9 (3)
C2—C3—C4—C5	0.9 (5)	O6—Eu1—N1—C2	43.2 (3)
O5—C4—C5—C6	178.0 (3)	O2—C1—O1—Eu1	172.3 (2)
C3—C4—C5—C6	−0.8 (4)	C2—C1—O1—Eu1	−9.0 (4)
C4—C5—C6—N1	0.2 (5)	O5ⁱ—Eu1—O1—C1	−163.2 (2)
C4—C5—C6—C7	−179.0 (3)	O8—Eu1—O1—C1	79.2 (3)
N1—C6—C7—O4	177.2 (3)	O7—Eu1—O1—C1	−70.3 (3)
C5—C6—C7—O4	−3.5 (5)	O2ⁱⁱ—Eu1—O1—C1	149.0 (3)
N1—C6—C7—O3	−1.8 (4)	O3—Eu1—O1—C1	6.0 (3)
C5—C6—C7—O3	177.4 (3)	O6—Eu1—O1—C1	−137.8 (3)
C5—C6—N1—C2	0.3 (5)	N1—Eu1—O1—C1	5.0 (3)
C7—C6—N1—C2	179.6 (3)	O1—C1—O2—Eu1ⁱⁱⁱ	−29.7 (5)
C5—C6—N1—Eu1	−173.3 (2)	C2—C1—O2—Eu1ⁱⁱⁱ	151.6 (2)
C7—C6—N1—Eu1	6.0 (4)	O4—C7—O3—Eu1	177.6 (2)
C3—C2—N1—C6	−0.2 (5)	C6—C7—O3—Eu1	−3.4 (4)
C1—C2—N1—C6	−177.8 (3)	O5ⁱ—Eu1—O3—C7	178.4 (3)
C3—C2—N1—Eu1	173.5 (2)	O8—Eu1—O3—C7	−78.2 (3)
C1—C2—N1—Eu1	−4.1 (4)	O7—Eu1—O3—C7	90.6 (3)
O5ⁱ—Eu1—N1—C6	−15.8 (3)	O1—Eu1—O3—C7	3.6 (3)
O8—Eu1—N1—C6	74.1 (2)	O2ⁱⁱ—Eu1—O3—C7	−115.4 (2)
O7—Eu1—N1—C6	−83.8 (2)	O6—Eu1—O3—C7	114.7 (2)
O1—Eu1—N1—C6	173.6 (3)	N1—Eu1—O3—C7	4.6 (2)
O2ⁱⁱ—Eu1—N1—C6	125.5 (2)	C3—C4—O5—Eu1^iv	69.8 (4)
O3—Eu1—N1—C6	−5.5 (2)	C5—C4—O5—Eu1^iv	−108.9 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H1W···O9^v	0.90 (2)	1.85 (3)	2.696 (3)	158 (4)
O6—H2W···O9^vi	0.87 (2)	2.15 (3)	2.962 (4)	156 (4)
O7—H4W···O3^v	0.86 (2)	2.09 (3)	2.805 (3)	141 (4)
O8—H5W···O1ⁱⁱ	0.86 (2)	1.84 (2)	2.684 (4)	168 (4)
O8—H6W···O4^vii	0.87 (2)	1.83 (2)	2.696 (4)	173 (4)
O9—H7W···O2^viii	0.86 (2)	2.26 (3)	3.059 (4)	155 (5)
O9—H8W···O4	0.86 (2)	1.84 (2)	2.692 (4)	172 (6)

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

Experimental details

Crystal data
Chemical formula	[Eu(C₇H₂NO₅)(H₂O)₃]·H₂O
M_r	404.12
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.0041 (15), 7.5456 (11), 15.528 (2)
β (°)	104.890 (1)
V (Å³)	1132.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.58
Crystal size (mm)	0.35 × 0.32 × 0.31

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.246, 0.277
No. of measured, independent and observed [I > 2σ(I)] reflections	4884, 2023, 1856
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.065, 1.06
No. of reflections	2023
No. of parameters	196
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)	0.82, −1.69

Computer programs: APEX2 (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Eu1—O5ⁱ	2.327 (2)	Eu1—O2ⁱⁱ	2.433 (2)
Eu1—O8	2.401 (3)	Eu1—O3	2.440 (2)
Eu1—O7	2.416 (3)	Eu1—O6	2.445 (3)
Eu1—O1	2.432 (2)	Eu1—N1	2.498 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H1W···O9ⁱⁱⁱ	0.895 (19)	1.85 (3)	2.696 (3)	158 (4)
O6—H2W···O9^iv	0.867 (19)	2.15 (3)	2.962 (4)	156 (4)
O7—H4W···O3ⁱⁱⁱ	0.856 (19)	2.09 (3)	2.805 (3)	141 (4)
O8—H5W···O1ⁱⁱ	0.855 (19)	1.84 (2)	2.684 (4)	168 (4)
O8—H6W···O4^v	0.868 (18)	1.833 (19)	2.696 (4)	173 (4)
O9—H7W···O2^vi	0.861 (19)	2.26 (3)	3.059 (4)	155 (5)
O9—H8W···O4	0.861 (19)	1.84 (2)	2.692 (4)	172 (6)

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

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