Poly[(acetato-κ(2)O,O')aqua-(μ(4)-1H-benzimidazole-5,6-dicarboxyl-ato-κ(6)N(3):O(5),O(5'):O(5),O(6):O(6'))cerium(III)].

In the title compound, [Ce(C(9)H(4)N(2)O(4))(C(2)H(3)O(2))(H(2)O)](n), the Ce(III) ion is coordinated by five O atoms and one N atom from four 1H-benzimidazole-5,6-dicarboxyl-ato (L) ligands and by two O atoms from an acetate ligand and one aqua ligand, forming a slightly distorted tricapped trigonal-prismatic geometry. The L ligands are bridging, forming a layered polymer parallel to (010). In the crystal, O-H⋯O and N-H⋯O hydrogen bonds connect the polymer layers into a three-dimensional network.

Related literature

For background to 1H-benzimidazole-5,6-dicarboxyl­ate complexes and for related structures, see: Gao et al. (2008 ▶); Yao et al. (2008 ▶); Song, Wang, Hu et al. (2009 ▶); Song, Wang, Li et al. (2009 ▶).

Experimental

Crystal data

[Ce(C9H4N2O4)(C2H3O2)(H2O)]

M = 421.32

Triclinic,

a = 7.4577 (15) Å

b = 9.0399 (19) Å

c = 9.792 (2) Å

α = 86.895 (2)°

β = 86.510 (2)°

γ = 84.707 (2)°

V = 655.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 3.51 mm−1

T = 293 K

0.17 × 0.13 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.584, T max = 0.680

3390 measured reflections

2366 independent reflections

2194 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.054

S = 1.05

2321 reflections

203 parameters

130 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.74 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017503/lh5440sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017503/lh5440Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ce(C9H4N2O4)(C2H3O2)(H2O)]	Z = 2
Mr = 421.32	F(000) = 406
Triclinic, P1	Dx = 2.135 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4577 (15) Å	Cell parameters from 2613 reflections
b = 9.0399 (19) Å	θ = 2.1–25.2°
c = 9.792 (2) Å	µ = 3.51 mm−1
α = 86.895 (2)°	T = 293 K
β = 86.510 (2)°	Block, colorless
γ = 84.707 (2)°	0.17 × 0.13 × 0.11 mm
V = 655.3 (2) Å3

Bruker APEXII CCD diffractometer	2366 independent reflections
Radiation source: fine-focus sealed tube	2194 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.584, Tmax = 0.680	k = −10→7
3390 measured reflections	l = −11→10

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0217P)2 + 1.2938P] where P = (Fo2 + 2Fc2)/3
2321 reflections	(Δ/σ)max = 0.004
203 parameters	Δρmax = 0.74 e Å−3
130 restraints	Δρmin = −0.59 e Å−3

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.The number of independent reflections and the number of reflections used in the refinement are not the same,because we used 'omit -3 50' to enhance the '_diffrn_measured_fraction_theta_full'.

	x	y	z	Uiso*/Ueq
Ce1	0.35253 (3)	0.35579 (2)	0.893484 (19)	0.01339 (8)
O6	0.3692 (4)	0.0660 (3)	0.8693 (3)	0.0242 (6)
O5	0.5196 (3)	0.1955 (3)	0.7120 (3)	0.0224 (6)
O3	0.1354 (3)	0.5879 (3)	0.8893 (3)	0.0198 (6)
O4	0.1202 (3)	0.2775 (3)	1.0582 (2)	0.0181 (5)
O7	0.6258 (4)	0.2197 (3)	1.0107 (3)	0.0277 (7)
O1	0.4775 (3)	0.5295 (3)	0.7017 (3)	0.0235 (6)
O2	0.6399 (3)	0.5169 (3)	0.8819 (2)	0.0169 (5)
N1	0.1240 (4)	0.3026 (3)	0.7095 (3)	0.0185 (7)
N2	−0.1340 (4)	0.2436 (4)	0.6341 (3)	0.0199 (7)
C4	0.1286 (5)	0.3230 (4)	0.5663 (3)	0.0152 (7)
C5	−0.0343 (5)	0.2557 (4)	0.7418 (4)	0.0189 (8)
H5	−0.0745	0.2328	0.8315	0.023*
C6	−0.0331 (5)	0.2865 (4)	0.5188 (4)	0.0157 (7)
C7	−0.0694 (5)	0.3027 (4)	0.3812 (4)	0.0175 (8)
H7	−0.1804	0.2823	0.3516	0.021*
C3	0.2613 (5)	0.3736 (4)	0.4746 (4)	0.0147 (7)
H3	0.3695	0.3983	0.5059	0.018*
C2	0.2310 (5)	0.3871 (4)	0.3353 (3)	0.0130 (7)
C8	0.0645 (5)	0.3502 (4)	0.2889 (4)	0.0141 (7)
C10	0.4720 (5)	0.0728 (4)	0.7632 (4)	0.0235 (9)
C1	0.6200 (5)	0.5515 (4)	0.7549 (3)	0.0129 (7)
C9	−0.0166 (5)	0.6502 (4)	0.8595 (3)	0.0139 (7)
C11	0.5451 (11)	−0.0663 (6)	0.6954 (7)	0.084 (3)
H11A	0.6391	−0.1166	0.7478	0.126*
H11B	0.5930	−0.0413	0.6047	0.126*
H11C	0.4501	−0.1302	0.6901	0.126*
H7B	0.629 (6)	0.133 (3)	1.043 (5)	0.037 (14)*
H7A	0.717 (5)	0.259 (4)	1.032 (5)	0.045 (15)*
H2	−0.239 (3)	0.212 (5)	0.635 (5)	0.045 (15)*

	U11	U22	U33	U12	U13	U23
Ce1	0.01261 (12)	0.01670 (12)	0.01084 (11)	−0.00151 (8)	0.00020 (7)	−0.00120 (7)
O6	0.0253 (15)	0.0189 (14)	0.0274 (16)	−0.0020 (11)	0.0036 (12)	0.0014 (11)
O5	0.0166 (14)	0.0236 (15)	0.0257 (15)	0.0007 (11)	0.0058 (11)	−0.0019 (11)
O3	0.0172 (13)	0.0229 (14)	0.0189 (14)	0.0031 (11)	−0.0064 (11)	−0.0008 (11)
O4	0.0163 (13)	0.0249 (14)	0.0136 (13)	−0.0032 (11)	0.0028 (10)	−0.0062 (11)
O7	0.0244 (16)	0.0199 (15)	0.0401 (18)	−0.0023 (12)	−0.0165 (13)	0.0038 (13)
O1	0.0175 (14)	0.0368 (17)	0.0175 (14)	−0.0121 (12)	−0.0027 (11)	0.0062 (12)
O2	0.0178 (13)	0.0223 (14)	0.0114 (13)	−0.0066 (10)	−0.0004 (10)	0.0007 (10)
N1	0.0183 (16)	0.0247 (17)	0.0127 (15)	−0.0045 (13)	−0.0003 (12)	0.0010 (12)
N2	0.0151 (17)	0.0302 (19)	0.0146 (16)	−0.0066 (14)	0.0024 (13)	0.0016 (13)
C4	0.0174 (18)	0.0187 (18)	0.0090 (17)	0.0005 (14)	0.0004 (14)	−0.0010 (13)
C5	0.022 (2)	0.025 (2)	0.0090 (17)	−0.0024 (16)	0.0026 (14)	0.0013 (14)
C6	0.0124 (18)	0.0185 (19)	0.0153 (18)	−0.0013 (14)	0.0044 (14)	0.0015 (14)
C7	0.0126 (18)	0.024 (2)	0.0168 (19)	−0.0046 (15)	−0.0010 (14)	−0.0016 (15)
C3	0.0118 (17)	0.0191 (19)	0.0137 (18)	−0.0014 (14)	−0.0022 (14)	−0.0027 (14)
C2	0.0127 (17)	0.0126 (17)	0.0134 (17)	0.0004 (13)	0.0004 (14)	−0.0008 (13)
C8	0.0107 (17)	0.0172 (18)	0.0135 (18)	0.0037 (13)	−0.0006 (13)	−0.0003 (14)
C10	0.025 (2)	0.021 (2)	0.024 (2)	0.0016 (16)	0.0007 (17)	−0.0019 (16)
C1	0.0138 (18)	0.0101 (16)	0.0145 (18)	0.0017 (13)	−0.0010 (14)	−0.0013 (13)
C9	0.0136 (18)	0.0158 (18)	0.0127 (18)	−0.0054 (14)	0.0003 (14)	0.0019 (14)
C11	0.139 (7)	0.025 (3)	0.079 (5)	0.006 (3)	0.060 (5)	−0.014 (3)

Ce1—O4	2.422 (2)	N2—C5	1.342 (5)
Ce1—O3	2.529 (3)	N2—C6	1.376 (4)
Ce1—O2i	2.543 (2)	N2—H2	0.857 (10)
Ce1—O5	2.547 (3)	C4—C3	1.388 (5)
Ce1—O1	2.568 (2)	C4—C6	1.392 (5)
Ce1—O7	2.580 (3)	C5—H5	0.9300
Ce1—O6	2.634 (3)	C6—C7	1.388 (5)
Ce1—N1	2.646 (3)	C7—C8	1.388 (5)
Ce1—O2	2.693 (2)	C7—H7	0.9300
Ce1—C10	2.960 (4)	C3—C2	1.394 (5)
Ce1—C1	3.002 (3)	C3—H3	0.9300
O6—C10	1.256 (5)	C2—C8	1.422 (5)
O5—C10	1.265 (5)	C2—C1iii	1.505 (5)
O3—C9	1.262 (4)	C8—C9iv	1.518 (5)
O4—C9ii	1.249 (4)	C10—C11	1.496 (6)
O7—H7B	0.830 (18)	C1—C2iii	1.505 (5)
O7—H7A	0.837 (18)	C9—O4ii	1.249 (4)
O1—C1	1.248 (4)	C9—C8iv	1.518 (5)
O2—C1	1.280 (4)	C11—H11A	0.9600
O2—Ce1i	2.543 (2)	C11—H11B	0.9600
N1—C5	1.306 (5)	C11—H11C	0.9600
N1—C4	1.403 (5)
O4—Ce1—O3	80.07 (8)	C9—O3—Ce1	148.6 (2)
O4—Ce1—O2i	68.71 (8)	C9ii—O4—Ce1	131.1 (2)
O3—Ce1—O2i	70.91 (8)	Ce1—O7—H7B	124 (3)
O4—Ce1—O5	125.69 (8)	Ce1—O7—H7A	126 (3)
O3—Ce1—O5	134.99 (8)	H7B—O7—H7A	110 (3)
O2i—Ce1—O5	148.20 (8)	C1—O1—Ce1	97.7 (2)
O4—Ce1—O1	153.50 (9)	C1—O2—Ce1i	139.2 (2)
O3—Ce1—O1	74.17 (9)	C1—O2—Ce1	90.97 (19)
O2i—Ce1—O1	107.59 (8)	Ce1i—O2—Ce1	109.06 (8)
O5—Ce1—O1	71.89 (9)	C5—N1—C4	104.1 (3)
O4—Ce1—O7	97.53 (9)	C5—N1—Ce1	123.3 (2)
O3—Ce1—O7	144.86 (9)	C4—N1—Ce1	132.5 (2)
O2i—Ce1—O7	75.57 (9)	C5—N2—C6	107.0 (3)
O5—Ce1—O7	74.44 (9)	C5—N2—H2	127 (3)
O1—Ce1—O7	107.06 (9)	C6—N2—H2	126 (3)
O4—Ce1—O6	76.55 (8)	C3—C4—C6	120.0 (3)
O3—Ce1—O6	142.29 (8)	C3—C4—N1	130.5 (3)
O2i—Ce1—O6	125.00 (8)	C6—C4—N1	109.5 (3)
O5—Ce1—O6	50.21 (8)	N1—C5—N2	114.1 (3)
O1—Ce1—O6	121.56 (9)	N1—C5—H5	122.9
O7—Ce1—O6	68.14 (9)	N2—C5—H5	122.9
O4—Ce1—N1	84.39 (9)	N2—C6—C7	132.6 (3)
O3—Ce1—N1	76.65 (9)	N2—C6—C4	105.3 (3)
O2i—Ce1—N1	140.60 (9)	C7—C6—C4	122.0 (3)
O5—Ce1—N1	71.10 (9)	C8—C7—C6	118.1 (3)
O1—Ce1—N1	83.75 (9)	C8—C7—H7	121.0
O7—Ce1—N1	138.34 (10)	C6—C7—H7	121.0
O6—Ce1—N1	72.00 (9)	C4—C3—C2	119.4 (3)
O4—Ce1—O2	139.30 (8)	C4—C3—H3	120.3
O3—Ce1—O2	91.88 (8)	C2—C3—H3	120.3
O2i—Ce1—O2	70.94 (9)	C3—C2—C8	119.8 (3)
O5—Ce1—O2	87.74 (8)	C3—C2—C1iii	115.2 (3)
O1—Ce1—O2	49.17 (8)	C8—C2—C1iii	124.9 (3)
O7—Ce1—O2	67.05 (8)	C7—C8—C2	120.7 (3)
O6—Ce1—O2	124.89 (8)	C7—C8—C9iv	113.4 (3)
N1—Ce1—O2	132.72 (8)	C2—C8—C9iv	125.8 (3)
O4—Ce1—C10	101.21 (10)	O6—C10—O5	121.6 (4)
O3—Ce1—C10	146.18 (10)	O6—C10—C11	120.3 (4)
O2i—Ce1—C10	141.48 (9)	O5—C10—C11	118.1 (4)
O5—Ce1—C10	25.14 (10)	O6—C10—Ce1	62.8 (2)
O1—Ce1—C10	96.82 (10)	O5—C10—Ce1	58.8 (2)
O7—Ce1—C10	68.91 (10)	C11—C10—Ce1	176.0 (4)
O6—Ce1—C10	25.08 (9)	O1—C1—O2	120.3 (3)
N1—Ce1—C10	69.91 (10)	O1—C1—C2iii	118.3 (3)
O2—Ce1—C10	106.88 (10)	O2—C1—C2iii	121.4 (3)
O4—Ce1—C1	158.49 (9)	O1—C1—Ce1	57.99 (18)
O3—Ce1—C1	85.24 (9)	O2—C1—Ce1	63.79 (17)
O2i—Ce1—C1	91.70 (9)	C2iii—C1—Ce1	164.7 (2)
O5—Ce1—C1	75.70 (9)	O4ii—C9—O3	123.6 (3)
O1—Ce1—C1	24.32 (9)	O4ii—C9—C8iv	119.0 (3)
O7—Ce1—C1	85.50 (9)	O3—C9—C8iv	117.0 (3)
O6—Ce1—C1	123.78 (9)	C10—C11—H11A	109.5
N1—Ce1—C1	107.48 (9)	C10—C11—H11B	109.5
O2—Ce1—C1	25.24 (8)	H11A—C11—H11B	109.5
C10—Ce1—C1	99.75 (10)	C10—C11—H11C	109.5
C10—O6—Ce1	92.2 (2)	H11A—C11—H11C	109.5
C10—O5—Ce1	96.0 (2)	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5v	0.86 (3)	1.93 (3)	2.716 (4)	153 (4)
O7—H7A···O3i	0.84 (4)	2.05 (4)	2.850 (4)	158 (3)
O7—H7B···O6vi	0.83 (3)	1.95 (3)	2.777 (4)	176 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5i	0.86 (3)	1.93 (3)	2.716 (4)	153 (4)
O7—H7A⋯O3ii	0.84 (4)	2.05 (4)	2.850 (4)	158 (3)
O7—H7B⋯O6iii	0.83 (3)	1.95 (3)	2.777 (4)	176 (6)

Symmetry codes: (i) ; (ii) ; (iii) .