A one-dimensional triaqua­europium(III)–1H,3H-benzimidazol-3-ium-5,6-dicarboxyl­ate–sulfate polymeric structure

Cai, X.; Lin, J.-J.; Chen, H.-Z.; Chen, L.-C.; Zeng, R.-H.

doi:10.1107/S1600536811034337

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1310-m1311

doi:10.1107/S1600536811034337

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A one-dimensional triaquaeuropium(III)–1H,3H-benzimidazol-3-ium-5,6-dicarboxylate–sulfate polymeric structure

Xia Cai,^a Jing-Jun Lin,^a Hao-Zhao Chen,^a Lai-Chen Chen ^a and Rong-Hua Zeng ^a,^b ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and ^bKey Laboratory of Technology of Electrochemical Energy Storage and Power Generation in Guangdong Universities, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: zrh321@yahoo.com.cn

(Received 5 August 2011; accepted 21 August 2011; online 27 August 2011)

In the title coordination polymer, catena-poly[[[triaquaeuropium(III)]-bis(μ-1H,3H-benzimidazol-3-ium-5,6-dicarboxylato-κ³O⁵,O^5′:O⁶)-[triaquaeuropium(III)]-di-μ-sulfato-κ³O:O,O′;κ³O,O′:O′] hexahydrate], [Eu₂(C₉H₅N₂O₄)₂(SO₄)₂(H₂O)₆]·6H₂O}_n, the 1H,3H-benzimidazol-3-ium-5,6-dicarboxylate ligand is protonated at the imidazole group (H₂bdc). The Eu^III ion is coordinated by nine O atoms from two H₂bdc ligands, two sulfate anions and three water molecules, displaying a bicapped trigonal prismatic geometry. The carboxylate groups of the H₂bdc ligands and the sulfate anions link the Eu^III ions, forming a chain along [010]. These chains are further connected by N—H⋯O and O—H⋯O hydrogen bonds and π–π interactions between the imidazole and benzene rings [centroid–centroid distances = 3.997 (4), 3.829 (4) and 3.573 (4) Å] into a three-dimensional supramolecular network.

Related literature

For background to 1H-benzimidazole-5,6-dicarboxylate complexes, see: Wang et al. (2010 ); Wei et al. (2008 ); Xie et al. (2010 ); Yao et al. (2008 ).

Experimental

Crystal data

[Eu₂(C₉H₅N₂O₄)₂(SO₄)₂(H₂O)₆]·6H₂O
M_r = 1122.58
Triclinic, $[P \overline 1]$
a = 7.1261 (16) Å
b = 9.581 (2) Å
c = 12.424 (3) Å
α = 100.496 (3)°
β = 98.060 (3)°
γ = 94.979 (3)°
V = 820.3 (3) Å³
Z = 1
Mo Kα radiation
μ = 4.03 mm⁻¹
T = 298 K
0.30 × 0.26 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.310, T_max = 0.446
4076 measured reflections
2841 independent reflections
2669 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.02
2841 reflections
248 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.82 e Å⁻³
Δρ_min = −2.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O4ⁱ	0.84	1.90	2.717 (6)	165
O1W—H2W⋯O7ⁱⁱ	0.84	2.24	3.049 (6)	163
O2W—H3W⋯O5ⁱⁱ	0.84	1.96	2.775 (6)	162
O2W—H4W⋯O3ⁱⁱⁱ	0.85	1.85	2.659 (6)	159
O3W—H5W⋯O4Wⁱⁱⁱ	0.84	2.07	2.810 (6)	146
O3W—H6W⋯O2^iv	0.85	2.10	2.864 (6)	149
O4W—H7W⋯O5ⁱⁱ	0.86	2.34	3.045 (6)	139
O4W—H8W⋯O1	0.84	2.04	2.869 (6)	168
O5W—H9W⋯O6W	0.84	2.03	2.864 (8)	171
O5W—H10W⋯O6^v	0.84	2.01	2.790 (7)	154
O6W—H11W⋯O6^vi	0.84	2.37	3.165 (8)	158
O6W—H12W⋯O5ⁱⁱ	0.85	2.20	2.895 (7)	139
O6W—H12W⋯O1W	0.85	2.46	3.060 (7)	129
N1—H1A⋯O5W^vii	0.86 (8)	1.96 (8)	2.752 (8)	153 (7)
N1—H1A⋯O4W^vii	0.86 (8)	2.48 (8)	2.989 (7)	119 (6)
N2—H2⋯O6W^viii	0.86	1.91	2.734 (7)	161
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z; (iii) -x+1, -y, -z; (iv) -x+2, -y, -z; (v) x, y, z+1; (vi) -x+2, -y+1, -z; (vii) -x+2, -y, -z+1; (viii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock global. DOI: 10.1107/S1600536811034337/hy2456sup1.cif

checkCIF report

Comment top

In recent years, research on coordination polymers has made considerable progress in the fields of supramolecular chemistry and crystal engineering, because of their intriguing structural motifs and functional properties, such as molecular adsorption, magnetism and luminescence. Ligands play a key role in the construction of coordination polymers with fascinating topology, intriguing architectures and useful physical-chemical properties. Benzimidazole-5,6-dicarboxylic acid (H₃bdc) is a potential bifunctional ligand with carboxylate and N-donor functional groups and has been used to prepare such metal-organic complexes in possession of multidimensional networks and interesting properties (Wang et al., 2010; Wei et al., 2008; Xie et al., 2010; Yao et al., 2008). Recently, we obtained the title coordination polymer, which was synthesized by the hydrothermal reaction of Eu₂O₃ with H₃bdc in an aqueous solution.

The title compound has a polymeric chain architecture. As shown in Fig. 1, the Eu^III ion is in a bicapped trigonal-prismatic geometry, defined by nine O atoms from two 1H,3H-benzimidazol-3-ium-5,6-dicarboxylate ligands (H₂bdc), which are protonated at the imidazole groups, two sulfate anions and three water molecules. The H₂bdc ligands and sulfate anions link the Eu^III ions into a chain along [0 1 0] (Fig. 2). The adjacent Eu···Eu separations are 4.272 (4) and 6.663 (5) Å. The Eu—O bond lengths range from 2.376 (4) to 2.610 (4) Å and O—Eu—O bond angles vary from 52.01 (1) to 143.68 (1) °. The chains are further connected by N—H···O and O—H···O hydrogen bonds (Table 1) and π–π interactions between the imidazole and benzene rings [centroid–centroid distances = 3.997 (4), 3.829 (4) and 3.573 (4) Å] into a three-dimensional supramolecular network.

Related literature top

For background to 1H-benzimidazole-5,6-dicarboxylate complexes, see: Wang et al. (2010); Wei et al. (2008); Xie et al. (2010); Yao et al. (2008).

Experimental top

A mixture of Eu₂O₃ (0.352 g, 1 mmol), H₃bdc (0.206 g, 1 mmol), water (10 ml) in the presence of H₂SO₄ (0.038 g, 0.385 mmol) was stirred vigorously for 30 min and then sealed in a 20 ml Teflon-lined stainless-steel autoclave. The autoclave was heated and maintained at 443 K for 3 days, and then cooled to room temperature at 5 K h^-1. Colorless block crystals of the title compound were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) 2-x, -y, -z; (ii) 2-x, 1-y, -z.]
	Fig. 2. A view of the chain structure along [0 1 0].

catena-poly[[[triaquaeuropium(III)]-bis(µ-1H,3H-benzimidazol-3-ium-5,6-dicarboxylato-κ³O⁵,O^5':O⁶)-[triaquaeuropium(III)]-di-µ-sulfato-κ³O:O,O';κ³O,O':O'] hexahydrate] top

Crystal data top

[Eu₂(C₉H₅N₂O₄)₂(SO₄)₂(H₂O)₆]·6H₂O	Z = 1
M_r = 1122.58	F(000) = 552
Triclinic, P1	D_x = 2.273 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1261 (16) Å	Cell parameters from 3240 reflections
b = 9.581 (2) Å	θ = 2.5–25.2°
c = 12.424 (3) Å	µ = 4.03 mm⁻¹
α = 100.496 (3)°	T = 298 K
β = 98.060 (3)°	Block, colorless
γ = 94.979 (3)°	0.30 × 0.26 × 0.20 mm
V = 820.3 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	2841 independent reflections
Radiation source: fine-focus sealed tube	2669 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.310, T_max = 0.446	k = −10→11
4076 measured reflections	l = −14→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0656P)² + 2.2735P] where P = (F_o² + 2F_c²)/3
2841 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 1.82 e Å⁻³
0 restraints	Δρ_min = −2.51 e Å⁻³

Crystal data top

[Eu₂(C₉H₅N₂O₄)₂(SO₄)₂(H₂O)₆]·6H₂O	γ = 94.979 (3)°
M_r = 1122.58	V = 820.3 (3) Å³
Triclinic, P1	Z = 1
a = 7.1261 (16) Å	Mo Kα radiation
b = 9.581 (2) Å	µ = 4.03 mm⁻¹
c = 12.424 (3) Å	T = 298 K
α = 100.496 (3)°	0.30 × 0.26 × 0.20 mm
β = 98.060 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2841 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2669 reflections with I > 2σ(I)
T_min = 0.310, T_max = 0.446	R_int = 0.024
4076 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 1.82 e Å⁻³
2841 reflections	Δρ_min = −2.51 e Å⁻³
248 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Eu1	0.82011 (3)	0.30949 (3)	−0.00038 (2)	0.01547 (13)
S3	0.7557 (2)	0.48078 (15)	−0.19659 (11)	0.0178 (3)
O1	0.8381 (6)	0.2686 (5)	0.1916 (3)	0.0245 (9)
O2	1.0266 (6)	0.1509 (4)	0.0920 (3)	0.0235 (9)
O7	0.6411 (6)	0.3533 (5)	−0.1756 (3)	0.0255 (9)
O8	0.9029 (5)	0.5245 (4)	−0.0939 (3)	0.0197 (8)
O5	0.6331 (6)	0.5948 (5)	−0.2072 (3)	0.0274 (9)
O6	0.8483 (7)	0.4467 (5)	−0.2935 (3)	0.0286 (10)
N1	1.3014 (7)	−0.0260 (6)	0.5455 (4)	0.0249 (11)
N2	1.2981 (7)	0.2039 (6)	0.5675 (4)	0.0251 (11)
H2	1.3174	0.2932	0.5979	0.030*
C1	0.9614 (8)	0.1832 (6)	0.1807 (5)	0.0190 (12)
C2	1.0383 (8)	0.1201 (6)	0.2791 (5)	0.0194 (12)
C3	1.0338 (8)	−0.0312 (6)	0.2662 (4)	0.0164 (11)
C5	1.1219 (8)	−0.0927 (6)	0.3485 (5)	0.0198 (12)
H5	1.1239	−0.1911	0.3393	0.024*
C6	1.2079 (8)	−0.0005 (6)	0.4462 (5)	0.0218 (12)
C7	1.2050 (8)	0.1468 (6)	0.4603 (5)	0.0213 (12)
C8	1.3518 (9)	0.0977 (7)	0.6146 (5)	0.0274 (14)
H8	1.4162	0.1086	0.6866	0.033*
C9	1.1232 (8)	0.2109 (6)	0.3771 (4)	0.0189 (11)
H9	1.1250	0.3095	0.3864	0.023*
O4W	0.5121 (7)	0.1310 (5)	0.2584 (4)	0.0352 (11)
H8W	0.6008	0.1653	0.2294	0.053*
H7W	0.4457	0.2009	0.2736	0.053*
O6W	0.7298 (9)	0.5166 (6)	0.3452 (4)	0.0439 (13)
H11W	0.8442	0.5054	0.3395	0.066*
H12W	0.6655	0.4779	0.2826	0.09 (4)*
O5W	0.6913 (11)	0.3173 (6)	0.4890 (5)	0.0644 (19)
H9W	0.6934	0.3808	0.4506	0.097*
H10W	0.7710	0.3559	0.5453	0.097*
O3W	0.7114 (6)	0.0596 (4)	−0.0781 (4)	0.0283 (10)
H5W	0.6097	0.0179	−0.1180	0.042*
H6W	0.7713	−0.0084	−0.0605	0.042*
O1W	0.7080 (6)	0.5224 (4)	0.0984 (4)	0.0266 (9)
H2W	0.6011	0.5504	0.1051	0.040*
H1W	0.7804	0.5996	0.1181	0.040*
O2W	0.4946 (6)	0.2615 (5)	0.0214 (4)	0.0308 (10)
H4W	0.4110	0.1952	−0.0161	0.046*
H3W	0.4346	0.3063	0.0678	0.046*
C4	0.9079 (8)	−0.1258 (6)	0.1673 (4)	0.0179 (11)
O4	0.9655 (6)	−0.2426 (4)	0.1255 (3)	0.0226 (9)
O3	0.7505 (6)	−0.0878 (5)	0.1382 (4)	0.0290 (10)
H1A	1.323 (11)	−0.109 (9)	0.557 (6)	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.01833 (18)	0.01343 (19)	0.01383 (18)	0.00052 (11)	0.00124 (11)	0.00220 (12)
S3	0.0222 (7)	0.0163 (7)	0.0138 (6)	−0.0006 (5)	0.0006 (5)	0.0030 (5)
O1	0.031 (2)	0.026 (2)	0.018 (2)	0.0101 (18)	0.0039 (17)	0.0053 (17)
O2	0.032 (2)	0.022 (2)	0.018 (2)	0.0070 (18)	0.0074 (17)	0.0046 (17)
O7	0.027 (2)	0.021 (2)	0.024 (2)	−0.0095 (17)	−0.0053 (17)	0.0065 (17)
O8	0.021 (2)	0.020 (2)	0.0140 (19)	−0.0041 (16)	−0.0042 (15)	0.0017 (16)
O5	0.034 (2)	0.023 (2)	0.024 (2)	0.0087 (18)	−0.0010 (18)	0.0051 (18)
O6	0.042 (3)	0.025 (2)	0.018 (2)	0.0020 (19)	0.0083 (18)	0.0016 (17)
N1	0.029 (3)	0.027 (3)	0.021 (3)	0.005 (2)	0.004 (2)	0.011 (2)
N2	0.033 (3)	0.022 (3)	0.016 (2)	−0.003 (2)	0.002 (2)	−0.001 (2)
C1	0.026 (3)	0.013 (3)	0.018 (3)	0.001 (2)	0.001 (2)	0.004 (2)
C2	0.018 (3)	0.020 (3)	0.020 (3)	0.000 (2)	0.004 (2)	0.004 (2)
C3	0.019 (3)	0.013 (3)	0.017 (3)	−0.001 (2)	0.003 (2)	0.002 (2)
C5	0.024 (3)	0.013 (3)	0.024 (3)	0.002 (2)	0.007 (2)	0.002 (2)
C6	0.024 (3)	0.022 (3)	0.020 (3)	0.000 (2)	0.005 (2)	0.007 (2)
C7	0.025 (3)	0.022 (3)	0.015 (3)	−0.002 (2)	0.005 (2)	0.002 (2)
C8	0.028 (3)	0.039 (4)	0.013 (3)	0.001 (3)	−0.002 (2)	0.007 (3)
C9	0.025 (3)	0.015 (3)	0.016 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
O4W	0.035 (2)	0.037 (3)	0.039 (3)	0.003 (2)	0.012 (2)	0.014 (2)
O6W	0.067 (4)	0.036 (3)	0.024 (3)	0.016 (3)	−0.003 (2)	−0.002 (2)
O5W	0.123 (6)	0.031 (3)	0.033 (3)	0.003 (3)	−0.006 (3)	0.007 (2)
O3W	0.030 (2)	0.019 (2)	0.032 (2)	−0.0014 (18)	−0.0022 (18)	0.0008 (18)
O1W	0.024 (2)	0.014 (2)	0.043 (3)	0.0046 (16)	0.0111 (19)	0.0037 (18)
O2W	0.023 (2)	0.035 (3)	0.028 (2)	−0.0041 (18)	0.0029 (18)	−0.0072 (19)
C4	0.024 (3)	0.015 (3)	0.015 (3)	−0.003 (2)	0.007 (2)	0.002 (2)
O4	0.030 (2)	0.019 (2)	0.019 (2)	0.0003 (17)	0.0081 (17)	−0.0012 (16)
O3	0.024 (2)	0.025 (2)	0.032 (2)	0.0055 (18)	−0.0039 (18)	−0.0061 (19)

Geometric parameters (Å, º) top

Eu1—O4ⁱ	2.374 (4)	C3—C5	1.375 (8)
Eu1—O2W	2.387 (4)	C3—C4	1.510 (8)
Eu1—O3W	2.427 (4)	C5—C6	1.392 (8)
Eu1—O8ⁱⁱ	2.434 (4)	C5—H5	0.9300
Eu1—O1W	2.439 (4)	C6—C7	1.392 (9)
Eu1—O1	2.474 (4)	C7—C9	1.381 (8)
Eu1—O2	2.518 (4)	C8—H8	0.9300
Eu1—O8	2.607 (4)	C9—H9	0.9300
S3—O6	1.451 (4)	O4W—H8W	0.8415
S3—O5	1.470 (4)	O4W—H7W	0.8612
S3—O7	1.493 (4)	O6W—H11W	0.8423
S3—O8	1.502 (4)	O6W—H12W	0.8471
O1—C1	1.256 (7)	O5W—H9W	0.8390
O2—C1	1.252 (7)	O5W—H10W	0.8403
N1—C8	1.319 (8)	O3W—H5W	0.8408
N1—C6	1.390 (8)	O3W—H6W	0.8534
N1—H1A	0.86 (8)	O1W—H2W	0.8393
N2—C8	1.322 (8)	O1W—H1W	0.8396
N2—C7	1.392 (7)	O2W—H4W	0.8507
N2—H2	0.8600	O2W—H3W	0.8434
C1—C2	1.517 (8)	C4—O3	1.235 (7)
C2—C9	1.387 (8)	C4—O4	1.272 (7)
C2—C3	1.426 (8)

O4ⁱ—Eu1—O2W	140.91 (14)	C8—N1—C6	108.3 (5)
O4ⁱ—Eu1—O3W	76.22 (15)	C8—N1—H1A	127 (5)
O2W—Eu1—O3W	71.09 (15)	C6—N1—H1A	124 (5)
O4ⁱ—Eu1—O8ⁱⁱ	81.63 (13)	C8—N2—C7	108.3 (5)
O2W—Eu1—O8ⁱⁱ	137.26 (14)	C8—N2—H2	125.8
O3W—Eu1—O8ⁱⁱ	143.77 (14)	C7—N2—H2	125.8
O4ⁱ—Eu1—O1W	140.46 (14)	O2—C1—O1	122.2 (5)
O2W—Eu1—O1W	69.33 (15)	O2—C1—C2	118.8 (5)
O3W—Eu1—O1W	140.36 (14)	O1—C1—C2	119.0 (5)
O8ⁱⁱ—Eu1—O1W	71.68 (14)	C9—C2—C3	121.4 (5)
O4ⁱ—Eu1—O1	126.79 (14)	C9—C2—C1	119.3 (5)
O2W—Eu1—O1	75.86 (15)	C3—C2—C1	119.1 (5)
O3W—Eu1—O1	92.05 (14)	C5—C3—C2	121.3 (5)
O8ⁱⁱ—Eu1—O1	78.65 (13)	C5—C3—C4	119.1 (5)
O1W—Eu1—O1	76.39 (14)	C2—C3—C4	119.1 (5)
O4ⁱ—Eu1—O2	75.47 (14)	C3—C5—C6	116.7 (5)
O2W—Eu1—O2	111.08 (15)	C3—C5—H5	121.6
O3W—Eu1—O2	69.40 (14)	C6—C5—H5	121.6
O8ⁱⁱ—Eu1—O2	77.54 (13)	N1—C6—C5	131.7 (6)
O1W—Eu1—O2	124.10 (14)	N1—C6—C7	106.4 (5)
O1—Eu1—O2	52.20 (13)	C5—C6—C7	121.8 (5)
O4ⁱ—Eu1—O8	71.41 (13)	C9—C7—N2	131.6 (6)
O2W—Eu1—O8	116.64 (14)	C9—C7—C6	122.3 (5)
O3W—Eu1—O8	131.57 (13)	N2—C7—C6	106.2 (5)
O8ⁱⁱ—Eu1—O8	64.15 (14)	N1—C8—N2	110.7 (5)
O1W—Eu1—O8	70.87 (13)	N1—C8—H8	124.6
O1—Eu1—O8	136.26 (13)	N2—C8—H8	124.6
O2—Eu1—O8	131.95 (13)	C7—C9—C2	116.4 (5)
O4ⁱ—Eu1—Eu1ⁱⁱ	73.90 (10)	C7—C9—H9	121.8
O2W—Eu1—Eu1ⁱⁱ	133.79 (11)	C2—C9—H9	121.8
O3W—Eu1—Eu1ⁱⁱ	149.81 (11)	H8W—O4W—H7W	104.3
O8ⁱⁱ—Eu1—Eu1ⁱⁱ	33.30 (9)	H11W—O6W—H12W	105.6
O1W—Eu1—Eu1ⁱⁱ	67.72 (10)	H9W—O5W—H10W	101.4
O1—Eu1—Eu1ⁱⁱ	109.19 (10)	Eu1—O3W—H5W	132.6
O2—Eu1—Eu1ⁱⁱ	106.55 (10)	Eu1—O3W—H6W	122.9
O8—Eu1—Eu1ⁱⁱ	30.84 (8)	H5W—O3W—H6W	104.1
O6—S3—O5	111.0 (3)	Eu1—O1W—H2W	135.5
O6—S3—O7	112.3 (3)	Eu1—O1W—H1W	120.5
O5—S3—O7	109.6 (3)	H2W—O1W—H1W	101.5
O6—S3—O8	110.1 (3)	Eu1—O2W—H4W	128.4
O5—S3—O8	110.2 (2)	Eu1—O2W—H3W	128.4
O7—S3—O8	103.5 (2)	H4W—O2W—H3W	103.2
C1—O1—Eu1	93.8 (3)	O3—C4—O4	125.0 (5)
C1—O2—Eu1	91.8 (3)	O3—C4—C3	116.9 (5)
S3—O8—Eu1ⁱⁱ	146.0 (2)	O4—C4—C3	117.9 (5)
S3—O8—Eu1	97.84 (18)	C4—O4—Eu1ⁱ	135.3 (4)
Eu1ⁱⁱ—O8—Eu1	115.85 (14)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O4ⁱⁱⁱ	0.84	1.90	2.717 (6)	165
O1W—H2W···O7^iv	0.84	2.24	3.049 (6)	163
O2W—H3W···O5^iv	0.84	1.96	2.775 (6)	162
O2W—H4W···O3^v	0.85	1.85	2.659 (6)	159
O3W—H5W···O4W^v	0.84	2.07	2.810 (6)	146
O3W—H6W···O2ⁱ	0.85	2.10	2.864 (6)	149
O4W—H7W···O5^iv	0.86	2.34	3.045 (6)	139
O4W—H8W···O1	0.84	2.04	2.869 (6)	168
O5W—H9W···O6W	0.84	2.03	2.864 (8)	171
O5W—H10W···O6^vi	0.84	2.01	2.790 (7)	154
O6W—H11W···O6ⁱⁱ	0.84	2.37	3.165 (8)	158
O6W—H12W···O5^iv	0.85	2.20	2.895 (7)	139
O6W—H12W···O1W	0.85	2.46	3.060 (7)	129
N1—H1A···O5W^vii	0.86 (8)	1.96 (8)	2.752 (8)	153 (7)
N1—H1A···O4W^vii	0.86 (8)	2.48 (8)	2.989 (7)	119 (6)
N2—H2···O6W^viii	0.86	1.91	2.734 (7)	161

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

Experimental details

Crystal data
Chemical formula	[Eu₂(C₉H₅N₂O₄)₂(SO₄)₂(H₂O)₆]·6H₂O
M_r	1122.58
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.1261 (16), 9.581 (2), 12.424 (3)
α, β, γ (°)	100.496 (3), 98.060 (3), 94.979 (3)
V (Å³)	820.3 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	4.03
Crystal size (mm)	0.30 × 0.26 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.310, 0.446
No. of measured, independent and observed [I > 2σ(I)] reflections	4076, 2841, 2669
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.02
No. of reflections	2841
No. of parameters	248
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.82, −2.51

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O4ⁱ	0.84	1.90	2.717 (6)	165
O1W—H2W···O7ⁱⁱ	0.84	2.24	3.049 (6)	163
O2W—H3W···O5ⁱⁱ	0.84	1.96	2.775 (6)	162
O2W—H4W···O3ⁱⁱⁱ	0.85	1.85	2.659 (6)	159
O3W—H5W···O4Wⁱⁱⁱ	0.84	2.07	2.810 (6)	146
O3W—H6W···O2^iv	0.85	2.10	2.864 (6)	149
O4W—H7W···O5ⁱⁱ	0.86	2.34	3.045 (6)	139
O4W—H8W···O1	0.84	2.04	2.869 (6)	168
O5W—H9W···O6W	0.84	2.03	2.864 (8)	171
O5W—H10W···O6^v	0.84	2.01	2.790 (7)	154
O6W—H11W···O6^vi	0.84	2.37	3.165 (8)	158
O6W—H12W···O5ⁱⁱ	0.85	2.20	2.895 (7)	139
O6W—H12W···O1W	0.85	2.46	3.060 (7)	129
N1—H1A···O5W^vii	0.86 (8)	1.96 (8)	2.752 (8)	153 (7)
N1—H1A···O4W^vii	0.86 (8)	2.48 (8)	2.989 (7)	119 (6)
N2—H2···O6W^viii	0.86	1.91	2.734 (7)	161

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

Acknowledgements

The authors acknowledge the Undergraduates' Innovating Experimentation Project of Guangdong Province, the Undergraduates' Innovating Experimentation Project of South China Normal University and the Students' Extracurricular Scientific Research Project of South China Normal University for supporting this work.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z.-X., Wu, X.-F., Liu, H.-J., Shao, M., Xiao, H.-P. & Li, M.-X. (2010). CrystEngComm, 12, 1139–1146. Google Scholar
Wei, Y.-Q., Yu, Y.-F. & Wu, K.-C. (2008). Cryst. Growth Des. 8, 2087–2089. Web of Science CrossRef CAS Google Scholar
Xie, Y., Xing, Y.-H., Wang, Z., Zhao, H.-Y., Zeng, X.-Q., Ge, M.-F. & Niu, S.-Y. (2010). Inorg. Chim. Acta, 363, 918–924. Google Scholar
Yao, Y.-L., Che, Y.-X. & Zheng, J.-M. (2008). Cryst. Growth Des. 8, 2299–2306. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 9| September 2011| Pages m1310-m1311

doi:10.1107/S1600536811034337

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

A one-dimensional tri­aqua­europium(III)–1H,3H-benzimidazol-3-ium-5,6-di­carboxyl­ate–sulfate polymeric structure

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

A one-dimensional triaquaeuropium(III)–1H,3H-benzimidazol-3-ium-5,6-dicarboxylate–sulfate polymeric structure