catena-Poly[[[2-(2-pyrid­yl)-1H-benz­imidazole]cadmium(II)]-μ-benzene-1,4-dicarboxyl­ato]

Liu, H.-Y.; Zhao, D.-W.; Sun, H.-M.

doi:10.1107/S1600536809026890

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m919

doi:10.1107/S1600536809026890

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catena-Poly[[[2-(2-pyridyl)-1H-benzimidazole]cadmium(II)]-μ-benzene-1,4-dicarboxylato]

Hai-Yan Liu,^a ^* Da-Wei Zhao ^a and Hong-Mei Sun ^a

^aDepartment of Chemistry and Pharmaceutical Engineering, Suihua University, Suihua 152061, People's Republic of China
^*Correspondence e-mail: lhy4486@yahoo.com.cn

(Received 27 June 2009; accepted 9 July 2009; online 15 July 2009)

In the title compound, [Cd(C₈H₄O₄)(C₁₂H₉N₃)]_n, each Cd^II ion is six-coordinated in a distorted octahedral geometry by four carboxylate O atoms from two benzene-1,4-dicarboxylate anions (L), and two N atoms from one 2-(2-pyridyl)benzimidazole ligand. The neighboring Cd^II ions are bridged by the L ligands, forming a zigzag polymeric chain structure. The chains are further extended into a three-dimensional supramolecular structure through intermolecular N—H⋯O hydrogen bonds.

Related literature

For metal-dicarboxylate complexes with aromatic N-donor chelating ligands, see: Robl (1992 ); Wang et al. (2006 ); Liu et al. (2008 ); Xia et al. (2007 ). For the synthesis, see: Addison & Burke (1981 ).

Experimental

Crystal data

[Cd(C₈H₄O₄)(C₁₂H₉N₃)]
M_r = 471.73
Monoclinic, P 2₁ /c
a = 7.378 (5) Å
b = 20.860 (5) Å
c = 11.546 (5) Å
β = 93.362 (5)°
V = 1773.9 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.26 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.16 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.750, T_max = 0.815
8112 measured reflections
3624 independent reflections
1967 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.052
S = 0.76
3624 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—O3ⁱ	2.271 (3)
Cd1—N1	2.278 (3)
Cd1—O2	2.318 (3)
Cd1—N2	2.322 (3)
Cd1—O1	2.338 (3)
Cd1—O4ⁱ	2.357 (3)
Symmetry code: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1A⋯O2ⁱⁱ	0.83 (2)	2.17 (3)	2.882 (5)	144 (4)
N3—H1A⋯O3ⁱⁱⁱ	0.83 (2)	2.46 (4)	2.988 (5)	123 (4)
Symmetry codes: (ii) -x+1, -y, -z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026890/ci2840sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026890/ci2840Isup2.hkl

checkCIF report

Comment top

In recent years, studies on metal-dicarboxylate complexes with aromatic N-donor chelating ligands have attracted special attention because of their interesting structural and chemical properties (Robl, 1992; Wang et al., 2006; Liu et al., 2008; Xia et al., 2007). Herein, we present a new cadmium-dicarboxylate complex (I), namely, [Cd(PyBM)L]_n, where PyBM is 2-(2-pyridyl)benzimidazole and L is benzene-1,4-dicarboxylic acid.

Selected bond distances are listed in Table 1. Each Cd^II center is six-coordinated by two N atoms of the chelating PyBM ligand and four O atoms from two L ions. The neighboring Cd^II ions are bridged by L ligands to form a zigzag polymeric chain structure (Fig. 2).

In the crystal structure, the adjacent chains are linked via N—H···O hydrogen bonds (Table 2) resulting in the formation of a three-dimensional supramolecular structure.

Related literature top

For metal-dicarboxylate complexes with aromatic N-donor chelating ligands, see: Robl (1992); Wang et al. (2006); Liu et al. (2008); Xia et al. (2007). For the synthesis, see: Addison et al. (1981).

Experimental top

2-(2-Pyridyl)benzimidazole was synthesized according to the literature method of Addison et al., (1981). A solution of Cd(CH₃COO)₂.2H₂O (0.133 g, 0.5 mmol), 2-(2-pyridyl)benzimidazole (0.097 g, 0.5 mmol), benzene-1,4-dicarboxylic acid (0.083 g, 0.5 mmol) in H₂O (10 ml) and CH₃OH (5 ml) was stirred under ambient conditions, then sealed in a Teflon-lined steel vessel, heated at 443 K for 3 d, and cooled to room temperature. The resulting product was recovered by filtration, washed with distilled water and dried in air (65% yield).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The coordination environment of the Cd^II ion in the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) 1 + x, 1/2 -y, 1/2 + z.
	Fig. 2. Part of the polymeric chain in the title compound.

catena-Poly[[[2-(2-pyridyl)-1H-benzimidazole]cadmium(II)]-µ- benzene-1,4-dicarboxylato] top

Crystal data top

[Cd(C₈H₄O₄)(C₁₂H₉N₃)]	F(000) = 936
M_r = 471.73	D_x = 1.766 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3624 reflections
a = 7.378 (5) Å	θ = 2.0–26.5°
b = 20.860 (5) Å	µ = 1.26 mm⁻¹
c = 11.546 (5) Å	T = 293 K
β = 93.362 (5)°	Block, colourless
V = 1773.9 (15) Å³	0.24 × 0.20 × 0.16 mm
Z = 4

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	3624 independent reflections
Radiation source: fine-focus sealed tube	1967 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.5°, θ_min = 2.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −20→25
T_min = 0.750, T_max = 0.815	l = −9→14
8112 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.052	H atoms treated by a mixture of independent and constrained refinement
S = 0.76	w = 1/[σ²(F_o²) + (0.0138P)²] where P = (F_o² + 2F_c²)/3
3624 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.47 e Å⁻³
1 restraint	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Cd(C₈H₄O₄)(C₁₂H₉N₃)]	V = 1773.9 (15) Å³
M_r = 471.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.378 (5) Å	µ = 1.26 mm⁻¹
b = 20.860 (5) Å	T = 293 K
c = 11.546 (5) Å	0.24 × 0.20 × 0.16 mm
β = 93.362 (5)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	3624 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1967 reflections with I > 2σ(I)
T_min = 0.750, T_max = 0.815	R_int = 0.052
8112 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.052	H atoms treated by a mixture of independent and constrained refinement
S = 0.76	Δρ_max = 0.47 e Å⁻³
3624 reflections	Δρ_min = −0.39 e Å⁻³
257 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
Cd1	0.79275 (4)	0.109528 (16)	0.34633 (3)	0.03417 (10)
C1	0.5456 (5)	0.14696 (17)	0.1841 (4)	0.0286 (10)
C2	0.4090 (5)	0.17967 (17)	0.1042 (3)	0.0256 (9)
C3	0.2232 (5)	0.17395 (19)	0.1229 (3)	0.0330 (11)
H3	0.1850	0.1461	0.1795	0.040*
C4	0.0980 (5)	0.20935 (18)	0.0576 (3)	0.0341 (10)
H4	−0.0251	0.2041	0.0685	0.041*
C5	0.1527 (5)	0.25280 (17)	−0.0243 (4)	0.0293 (10)
C6	0.3364 (5)	0.25629 (17)	−0.0456 (4)	0.0316 (10)
H6	0.3742	0.2834	−0.1034	0.038*
C7	0.4622 (5)	0.22008 (18)	0.0176 (3)	0.0318 (10)
H7	0.5842	0.2228	0.0020	0.038*
C8	0.0192 (5)	0.29813 (19)	−0.0795 (3)	0.0302 (10)
C9	0.7918 (6)	−0.0301 (2)	0.2117 (4)	0.0487 (13)
H9	0.8198	−0.0058	0.1477	0.058*
C10	0.7574 (6)	−0.0939 (2)	0.1950 (4)	0.0581 (14)
H10	0.7656	−0.1127	0.1225	0.070*
C11	0.7105 (6)	−0.1293 (2)	0.2886 (5)	0.0556 (14)
H11	0.6836	−0.1726	0.2800	0.067*
C12	0.7032 (5)	−0.1004 (2)	0.3951 (4)	0.0451 (11)
H12	0.6712	−0.1238	0.4593	0.054*
C13	0.7440 (5)	−0.03626 (19)	0.4051 (4)	0.0327 (10)
C14	0.7435 (5)	−0.00048 (19)	0.5139 (4)	0.0303 (10)
C15	0.7579 (5)	0.0770 (2)	0.6369 (4)	0.0333 (11)
C16	0.7781 (5)	0.1363 (2)	0.6920 (4)	0.0436 (12)
H16	0.7981	0.1737	0.6507	0.052*
C17	0.7668 (6)	0.1367 (2)	0.8101 (4)	0.0506 (14)
H17	0.7789	0.1756	0.8493	0.061*
C18	0.7379 (6)	0.0815 (2)	0.8736 (4)	0.0582 (14)
H18	0.7312	0.0842	0.9537	0.070*
C19	0.7192 (6)	0.0225 (2)	0.8197 (4)	0.0490 (13)
H19	0.6998	−0.0148	0.8613	0.059*
C20	0.7307 (5)	0.02185 (19)	0.7012 (4)	0.0339 (11)
N1	0.7647 (4)	0.06143 (15)	0.5215 (3)	0.0329 (8)
N2	0.7879 (4)	−0.00038 (16)	0.3145 (3)	0.0378 (9)
N3	0.7210 (5)	−0.02713 (18)	0.6197 (3)	0.0400 (10)
O1	0.7077 (4)	0.14386 (12)	0.1581 (3)	0.0435 (7)
O2	0.4940 (3)	0.12531 (12)	0.2787 (2)	0.0371 (8)
O3	0.0764 (3)	0.34878 (12)	−0.1266 (2)	0.0354 (7)
O4	−0.1483 (3)	0.28802 (12)	−0.0740 (2)	0.0403 (8)
H1A	0.701 (6)	−0.0642 (12)	0.642 (4)	0.080 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.03531 (15)	0.03201 (15)	0.03438 (19)	−0.00389 (19)	−0.00479 (12)	0.0038 (2)
C1	0.035 (2)	0.024 (2)	0.026 (3)	0.0038 (19)	−0.002 (2)	−0.0041 (19)
C2	0.031 (2)	0.024 (2)	0.022 (3)	0.0032 (18)	0.0023 (18)	0.0007 (19)
C3	0.034 (2)	0.036 (2)	0.029 (3)	−0.004 (2)	0.004 (2)	0.013 (2)
C4	0.028 (2)	0.045 (3)	0.029 (3)	−0.001 (2)	0.002 (2)	0.005 (2)
C5	0.032 (2)	0.025 (2)	0.031 (3)	0.0029 (19)	−0.0011 (19)	0.0009 (19)
C6	0.037 (2)	0.032 (2)	0.027 (3)	−0.004 (2)	0.006 (2)	0.004 (2)
C7	0.027 (2)	0.041 (3)	0.028 (3)	−0.004 (2)	0.005 (2)	−0.003 (2)
C8	0.036 (3)	0.033 (2)	0.021 (3)	0.000 (2)	−0.001 (2)	−0.008 (2)
C9	0.057 (3)	0.044 (3)	0.045 (4)	0.005 (2)	0.002 (2)	−0.004 (3)
C10	0.072 (3)	0.054 (4)	0.047 (4)	0.015 (3)	−0.004 (3)	−0.021 (3)
C11	0.062 (3)	0.036 (3)	0.067 (4)	0.007 (2)	−0.013 (3)	−0.020 (3)
C12	0.052 (3)	0.032 (3)	0.050 (3)	0.005 (2)	−0.005 (2)	0.001 (2)
C13	0.034 (2)	0.030 (3)	0.033 (3)	0.011 (2)	−0.005 (2)	−0.002 (2)
C14	0.026 (2)	0.030 (3)	0.034 (3)	0.0012 (19)	−0.003 (2)	0.005 (2)
C15	0.026 (2)	0.039 (3)	0.036 (3)	0.003 (2)	0.005 (2)	−0.003 (2)
C16	0.050 (3)	0.038 (3)	0.044 (4)	−0.003 (2)	0.008 (2)	−0.008 (2)
C17	0.052 (3)	0.058 (3)	0.043 (4)	−0.002 (3)	0.010 (3)	−0.020 (3)
C18	0.070 (4)	0.071 (4)	0.034 (4)	−0.004 (3)	0.007 (3)	−0.013 (3)
C19	0.055 (3)	0.060 (3)	0.032 (3)	−0.005 (2)	0.007 (2)	0.008 (3)
C20	0.031 (2)	0.037 (3)	0.034 (3)	0.003 (2)	0.002 (2)	−0.003 (2)
N1	0.041 (2)	0.028 (2)	0.029 (3)	−0.0010 (17)	0.0010 (17)	−0.0043 (17)
N2	0.046 (2)	0.041 (2)	0.025 (3)	−0.0010 (17)	−0.0062 (19)	−0.0089 (19)
N3	0.047 (2)	0.039 (2)	0.033 (3)	−0.003 (2)	0.001 (2)	0.004 (2)
O1	0.0297 (14)	0.0664 (18)	0.0346 (19)	0.0045 (16)	0.0043 (13)	0.0090 (17)
O2	0.0307 (14)	0.046 (2)	0.035 (2)	−0.0055 (13)	0.0037 (14)	0.0123 (15)
O3	0.0336 (16)	0.0359 (17)	0.037 (2)	0.0027 (13)	0.0036 (14)	0.0105 (14)
O4	0.0291 (16)	0.0356 (17)	0.056 (2)	−0.0032 (14)	−0.0015 (15)	0.0059 (15)

Geometric parameters (Å, º) top

Cd1—O3ⁱ	2.271 (3)	C9—H9	0.9300
Cd1—N1	2.278 (3)	C10—C11	1.369 (6)
Cd1—O2	2.318 (3)	C10—H10	0.9300
Cd1—N2	2.322 (3)	C11—C12	1.374 (6)
Cd1—O1	2.338 (3)	C11—H11	0.9300
Cd1—O4ⁱ	2.357 (3)	C12—C13	1.375 (5)
Cd1—C1	2.654 (4)	C12—H12	0.9300
Cd1—C8ⁱ	2.658 (4)	C13—N2	1.341 (5)
C1—O1	1.252 (4)	C13—C14	1.461 (6)
C1—O2	1.261 (4)	C14—N1	1.303 (4)
C1—C2	1.491 (5)	C14—N3	1.361 (5)
C2—C7	1.382 (5)	C15—N1	1.375 (5)
C2—C3	1.405 (5)	C15—C20	1.389 (5)
C3—C4	1.373 (5)	C15—C16	1.396 (5)
C3—H3	0.9300	C16—C17	1.372 (6)
C4—C5	1.387 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.389 (6)
C5—C6	1.394 (5)	C17—H17	0.9300
C5—C8	1.482 (5)	C18—C19	1.383 (6)
C6—C7	1.373 (5)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.376 (6)
C7—H7	0.9300	C19—H19	0.9300
C8—O4	1.259 (4)	C20—N3	1.387 (5)
C8—O3	1.272 (4)	N3—H1A	0.829 (19)
C8—Cd1ⁱⁱ	2.658 (4)	O3—Cd1ⁱⁱ	2.271 (3)
C9—N2	1.342 (5)	O4—Cd1ⁱⁱ	2.357 (3)
C9—C10	1.366 (5)

O3ⁱ—Cd1—N1	100.24 (11)	O3—C8—C5	119.0 (3)
O3ⁱ—Cd1—O2	147.38 (10)	O4—C8—Cd1ⁱⁱ	62.44 (19)
N1—Cd1—O2	103.14 (10)	O3—C8—Cd1ⁱⁱ	58.55 (19)
O3ⁱ—Cd1—N2	113.93 (11)	C5—C8—Cd1ⁱⁱ	171.9 (3)
N1—Cd1—N2	72.79 (12)	N2—C9—C10	124.2 (5)
O2—Cd1—N2	94.67 (10)	N2—C9—H9	117.9
O3ⁱ—Cd1—O1	101.85 (10)	C10—C9—H9	117.9
N1—Cd1—O1	157.89 (10)	C9—C10—C11	117.9 (5)
O2—Cd1—O1	56.34 (9)	C9—C10—H10	121.1
N2—Cd1—O1	98.89 (11)	C11—C10—H10	121.1
O3ⁱ—Cd1—O4ⁱ	56.74 (9)	C10—C11—C12	119.7 (4)
N1—Cd1—O4ⁱ	94.44 (11)	C10—C11—H11	120.2
O2—Cd1—O4ⁱ	98.78 (9)	C12—C11—H11	120.2
N2—Cd1—O4ⁱ	163.31 (11)	C11—C12—C13	118.8 (4)
O1—Cd1—O4ⁱ	96.78 (10)	C11—C12—H12	120.6
O3ⁱ—Cd1—C1	125.02 (11)	C13—C12—H12	120.6
N1—Cd1—C1	131.42 (12)	N2—C13—C12	122.6 (4)
O2—Cd1—C1	28.37 (9)	N2—C13—C14	113.5 (4)
N2—Cd1—C1	100.09 (11)	C12—C13—C14	123.9 (4)
O1—Cd1—C1	28.15 (10)	N1—C14—N3	111.4 (4)
O4ⁱ—Cd1—C1	96.43 (10)	N1—C14—C13	123.9 (4)
O3ⁱ—Cd1—C8ⁱ	28.54 (10)	N3—C14—C13	124.7 (4)
N1—Cd1—C8ⁱ	96.98 (11)	N1—C15—C20	109.7 (4)
O2—Cd1—C8ⁱ	124.94 (11)	N1—C15—C16	129.9 (4)
N2—Cd1—C8ⁱ	140.36 (12)	C20—C15—C16	120.4 (4)
O1—Cd1—C8ⁱ	101.92 (10)	C17—C16—C15	116.6 (4)
O4ⁱ—Cd1—C8ⁱ	28.26 (9)	C17—C16—H16	121.7
C1—Cd1—C8ⁱ	114.01 (12)	C15—C16—H16	121.7
O1—C1—O2	122.0 (4)	C16—C17—C18	122.7 (4)
O1—C1—C2	119.7 (4)	C16—C17—H17	118.7
O2—C1—C2	118.2 (3)	C18—C17—H17	118.7
O1—C1—Cd1	61.8 (2)	C19—C18—C17	121.0 (5)
O2—C1—Cd1	60.87 (19)	C19—C18—H18	119.5
C2—C1—Cd1	169.4 (3)	C17—C18—H18	119.5
C7—C2—C3	118.9 (4)	C20—C19—C18	116.5 (4)
C7—C2—C1	121.1 (3)	C20—C19—H19	121.7
C3—C2—C1	119.8 (3)	C18—C19—H19	121.7
C4—C3—C2	120.1 (3)	C19—C20—N3	132.7 (4)
C4—C3—H3	120.0	C19—C20—C15	122.8 (4)
C2—C3—H3	120.0	N3—C20—C15	104.5 (4)
C3—C4—C5	120.8 (3)	C14—N1—C15	106.7 (3)
C3—C4—H4	119.6	C14—N1—Cd1	113.2 (3)
C5—C4—H4	119.6	C15—N1—Cd1	140.1 (3)
C4—C5—C6	118.7 (4)	C13—N2—C9	116.8 (4)
C4—C5—C8	119.8 (4)	C13—N2—Cd1	115.5 (3)
C6—C5—C8	121.3 (4)	C9—N2—Cd1	126.6 (3)
C7—C6—C5	120.7 (4)	C14—N3—C20	107.7 (4)
C7—C6—H6	119.6	C14—N3—H1A	134 (4)
C5—C6—H6	119.6	C20—N3—H1A	119 (4)
C6—C7—C2	120.6 (4)	C1—O1—Cd1	90.1 (2)
C6—C7—H7	119.7	C1—O2—Cd1	90.8 (2)
C2—C7—H7	119.7	C8—O3—Cd1ⁱⁱ	92.9 (2)
O4—C8—O3	120.8 (4)	C8—O4—Cd1ⁱⁱ	89.3 (2)
O4—C8—C5	120.1 (4)

O3ⁱ—Cd1—C1—O1	38.9 (3)	C20—C15—N1—C14	−0.2 (4)
N1—Cd1—C1—O1	−165.9 (2)	C16—C15—N1—C14	178.1 (4)
O2—Cd1—C1—O1	−171.1 (4)	C20—C15—N1—Cd1	177.6 (3)
N2—Cd1—C1—O1	−90.0 (2)	C16—C15—N1—Cd1	−4.1 (7)
O4ⁱ—Cd1—C1—O1	92.4 (2)	O3ⁱ—Cd1—N1—C14	−118.0 (3)
C8ⁱ—Cd1—C1—O1	69.3 (2)	O2—Cd1—N1—C14	84.9 (3)
O3ⁱ—Cd1—C1—O2	−150.07 (19)	N2—Cd1—N1—C14	−6.0 (3)
N1—Cd1—C1—O2	5.1 (3)	O1—Cd1—N1—C14	64.6 (4)
N2—Cd1—C1—O2	81.0 (2)	O4ⁱ—Cd1—N1—C14	−175.0 (3)
O1—Cd1—C1—O2	171.1 (4)	C1—Cd1—N1—C14	82.4 (3)
O4ⁱ—Cd1—C1—O2	−96.6 (2)	C8ⁱ—Cd1—N1—C14	−146.7 (3)
C8ⁱ—Cd1—C1—O2	−119.6 (2)	O3ⁱ—Cd1—N1—C15	64.3 (4)
O3ⁱ—Cd1—C1—C2	−62.2 (16)	O2—Cd1—N1—C15	−92.8 (4)
N1—Cd1—C1—C2	93.0 (16)	N2—Cd1—N1—C15	176.3 (4)
O2—Cd1—C1—C2	87.9 (16)	O1—Cd1—N1—C15	−113.1 (4)
N2—Cd1—C1—C2	168.9 (16)	O4ⁱ—Cd1—N1—C15	7.3 (4)
O1—Cd1—C1—C2	−101.1 (16)	C1—Cd1—N1—C15	−95.3 (4)
O4ⁱ—Cd1—C1—C2	−8.7 (16)	C8ⁱ—Cd1—N1—C15	35.6 (4)
C8ⁱ—Cd1—C1—C2	−31.8 (16)	C12—C13—N2—C9	−0.5 (6)
O1—C1—C2—C7	−16.2 (6)	C14—C13—N2—C9	179.7 (3)
O2—C1—C2—C7	161.1 (4)	C12—C13—N2—Cd1	168.0 (3)
Cd1—C1—C2—C7	79.0 (17)	C14—C13—N2—Cd1	−11.8 (4)
O1—C1—C2—C3	169.3 (4)	C10—C9—N2—C13	−1.2 (6)
O2—C1—C2—C3	−13.4 (5)	C10—C9—N2—Cd1	−168.2 (3)
Cd1—C1—C2—C3	−95.5 (16)	O3ⁱ—Cd1—N2—C13	103.7 (3)
C7—C2—C3—C4	−1.6 (6)	N1—Cd1—N2—C13	9.9 (3)
C1—C2—C3—C4	173.0 (4)	O2—Cd1—N2—C13	−92.5 (3)
C2—C3—C4—C5	−2.4 (6)	O1—Cd1—N2—C13	−149.1 (3)
C3—C4—C5—C6	5.0 (6)	O4ⁱ—Cd1—N2—C13	51.2 (5)
C3—C4—C5—C8	−169.8 (4)	C1—Cd1—N2—C13	−120.6 (3)
C4—C5—C6—C7	−3.6 (6)	C8ⁱ—Cd1—N2—C13	89.8 (3)
C8—C5—C6—C7	171.1 (4)	O3ⁱ—Cd1—N2—C9	−89.2 (3)
C5—C6—C7—C2	−0.4 (6)	N1—Cd1—N2—C9	177.0 (4)
C3—C2—C7—C6	3.0 (6)	O2—Cd1—N2—C9	74.7 (3)
C1—C2—C7—C6	−171.6 (3)	O1—Cd1—N2—C9	18.1 (4)
C4—C5—C8—O4	−16.7 (6)	O4ⁱ—Cd1—N2—C9	−141.6 (4)
C6—C5—C8—O4	168.7 (4)	C1—Cd1—N2—C9	46.6 (4)
C4—C5—C8—O3	159.5 (4)	C8ⁱ—Cd1—N2—C9	−103.0 (4)
C6—C5—C8—O3	−15.1 (6)	N1—C14—N3—C20	−0.7 (5)
N2—C9—C10—C11	2.1 (7)	C13—C14—N3—C20	179.3 (4)
C9—C10—C11—C12	−1.3 (7)	C19—C20—N3—C14	−179.2 (4)
C10—C11—C12—C13	−0.2 (6)	C15—C20—N3—C14	0.5 (4)
C11—C12—C13—N2	1.1 (6)	O2—C1—O1—Cd1	−9.2 (4)
C11—C12—C13—C14	−179.1 (4)	C2—C1—O1—Cd1	168.0 (3)
N2—C13—C14—N1	6.8 (6)	O3ⁱ—Cd1—O1—C1	−148.3 (2)
C12—C13—C14—N1	−173.0 (4)	N1—Cd1—O1—C1	29.0 (4)
N2—C13—C14—N3	−173.2 (4)	O2—Cd1—O1—C1	5.1 (2)
C12—C13—C14—N3	7.0 (6)	N2—Cd1—O1—C1	94.8 (2)
N1—C15—C16—C17	−179.1 (4)	O4ⁱ—Cd1—O1—C1	−91.0 (2)
C20—C15—C16—C17	−0.9 (6)	C8ⁱ—Cd1—O1—C1	−119.1 (2)
C15—C16—C17—C18	0.4 (7)	O1—C1—O2—Cd1	9.3 (4)
C16—C17—C18—C19	0.1 (7)	C2—C1—O2—Cd1	−167.9 (3)
C17—C18—C19—C20	0.0 (7)	O3ⁱ—Cd1—O2—C1	49.3 (3)
C18—C19—C20—N3	179.1 (4)	N1—Cd1—O2—C1	−176.0 (2)
C18—C19—C20—C15	−0.6 (6)	N2—Cd1—O2—C1	−102.6 (2)
N1—C15—C20—C19	179.6 (4)	O1—Cd1—O2—C1	−5.1 (2)
C16—C15—C20—C19	1.1 (6)	O4ⁱ—Cd1—O2—C1	87.3 (2)
N1—C15—C20—N3	−0.2 (4)	C8ⁱ—Cd1—O2—C1	75.6 (3)
C16—C15—C20—N3	−178.7 (4)	O4—C8—O3—Cd1ⁱⁱ	5.2 (4)
N3—C14—N1—C15	0.6 (4)	C5—C8—O3—Cd1ⁱⁱ	−171.0 (3)
C13—C14—N1—C15	−179.4 (3)	O3—C8—O4—Cd1ⁱⁱ	−5.0 (4)
N3—C14—N1—Cd1	−177.9 (2)	C5—C8—O4—Cd1ⁱⁱ	171.2 (3)
C13—C14—N1—Cd1	2.1 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1A···O2ⁱⁱⁱ	0.83 (2)	2.17 (3)	2.882 (5)	144 (4)
N3—H1A···O3^iv	0.83 (2)	2.46 (4)	2.988 (5)	123 (4)

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

Experimental details

Crystal data
Chemical formula	[Cd(C₈H₄O₄)(C₁₂H₉N₃)]
M_r	471.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.378 (5), 20.860 (5), 11.546 (5)
β (°)	93.362 (5)
V (Å³)	1773.9 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.26
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.750, 0.815
No. of measured, independent and observed [I > 2σ(I)] reflections	8112, 3624, 1967
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.052, 0.76
No. of reflections	3624
No. of parameters	257
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.39

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Selected bond lengths (Å) top

Cd1—O3ⁱ	2.271 (3)	Cd1—N2	2.322 (3)
Cd1—N1	2.278 (3)	Cd1—O1	2.338 (3)
Cd1—O2	2.318 (3)	Cd1—O4ⁱ	2.357 (3)

Symmetry code: (i) x+1, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1A···O2ⁱⁱ	0.83 (2)	2.17 (3)	2.882 (5)	144 (4)
N3—H1A···O3ⁱⁱⁱ	0.83 (2)	2.46 (4)	2.988 (5)	123 (4)

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

Acknowledgements

The authors thank the Science Foundation of Suihua University (grant No. K081001) for supporting this work.

References

Addison, A. W. & Burke, P. J. (1981). J. Heterocycl. Chem. 18, 803–805. CrossRef CAS Google Scholar
Liu, G.-X., Huang, R.-Y., Xu, H., Kong, X.-J., Huang, L.-F., Zhu, K. & Ren, X.-M. (2008). Polyhedron, 27, 2327–2336. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Robl, C. (1992). Mater. Res. Bull. 27, 99–107. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, X.-L., Qin, C., Wang, E.-B. & Xu, L. (2006). Cryst. Growth Des. 6, 2061–2065. Web of Science CSD CrossRef CAS Google Scholar
Xia, C.-K., Wu, W., Chen, Q.-Y. & Xie, J.-M. (2007). Acta Cryst. E63, m2726. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page m919

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

catena-Poly[[[2-(2-pyrid­yl)-1H-benz­imidazole]cadmium(II)]-μ-benzene-1,4-di­carboxyl­ato]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[[[2-(2-pyridyl)-1H-benzimidazole]cadmium(II)]-μ-benzene-1,4-dicarboxylato]