catena-Poly[[bis­(acetato-κ2O,O′)cobalt(II)]-μ-4,4′-bis­(benzimidazol-1-yl)biphenyl-κ2N3:N3′]

Huang, P.-Y.; Wang, J.-G.

doi:10.1107/S160053681004715X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1638

https://doi.org/10.1107/S160053681004715X

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catena-Poly[[bis(acetato-κ²O,O′)cobalt(II)]-μ-4,4′-bis(benzimidazol-1-yl)biphenyl-κ²N³:N^3′]

Ping-Yun Huang ^a ^* and Jin-Guo Wang ^a

^aCollege of Science, Chang'an University, Xi'an 710064, Shaanxi, People's Republic of China
^*Correspondence e-mail: jtxb2010@163.com

(Received 26 October 2010; accepted 14 November 2010; online 24 November 2010)

In the title one-dimensional coordination polymer, [Co(C₂H₃O₂)₂(C₂₆H₁₈N₄)]_n, the Co^II atom (site symmetry 2) is coordinated by two O,O′-bidentate acetate ions and two 4,4′-bis(benzimidazol-1-yl)biphenyl ligands in a distorted cis-CoN₂O₄ octahedral geometry. The bridging ligand, which is completed by crystallographic twofold symmetry, links the Co^II atoms into [10 $[\overline{1}]$ ] chains. Within the ligand, the dihedral angle between the benzene and benzimidazole rings is 48.31 (8)°.

Related literature

For background to benzimidazole-derived ligands in coordination polymers, see: Jin et al. (2006 ); Li et al. (2010 ); Su et al. (2003 ).

Experimental

Crystal data

[Co(C₂H₃O₂)₂(C₂₆H₁₈N₄)]
M_r = 563.46
Orthorhombic, P b c n
a = 13.078 (3) Å
b = 16.348 (3) Å
c = 11.354 (2) Å
V = 2427.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.18 mm

Data collection

Rigaku CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.828, T_max = 0.873
21778 measured reflections
2150 independent reflections
2101 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.083
S = 1.10
2150 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O1	2.0386 (16)
Co1—O2	2.4163 (18)
Co1—N1	2.0709 (16)

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S160053681004715X/hb5708sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004715X/hb5708Isup2.hkl

checkCIF report

Comment top

Benzoimidazole has been well used in crystal engineering, and a large number of benzoimidazole-containing flexible ligands have been extensively studied (Su et al.,2003; Jin et al.,2006). However, to our knowledge, the research on benzoimidazole ligands bearing rigid spacers is still less developed (Li et al.,2010).

Single-crystal X-ray diffraction analysis reveals that the title compound (I) crystallizes in the orthorhombic space group Pbcn. The geometry of the Co^II ion is surrounded by two benzoiimidazole rings of distinct L ligands and two chelated acetate anions, which illustrates a slightly distorted octahedral coordination environment (Fig. 1). Notably, as shown in Fig. 2, the six-coordinated Co^II center is bridged by the linear ligand L to form an infinite one-dimensional architecture.

Related literature top

For background to benzimidazole-derived ligands in coordination polymers, see: Jin et al. (2006); Li et al. (2010); Su et al. (2003).

Experimental top

A mixture of CH₃OH and CHCl₃ (1:1, 8 ml), as a buffer layer, was carefully layered over a solution of 4,4'-bis(benzoimidazol-1-yl)terphenyl (L, 0.06 mmol) in CHCl₃ (6 ml). Then a solution of Co(CH₃COO)₂ (0.02 mmol) in CH₃OH (6 ml) was layered over the buffer layer, and the resultant reaction was left to stand at room temperature. After ca three weeks, purple blocks of (I) appeared at the boundary. Yield: ~25% (based on L).

Structure description top

For background to benzimidazole-derived ligands in coordination polymers, see: Jin et al. (2006); Li et al. (2010); Su et al. (2003).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The crystal packing for (I).

catena-Poly[[bis(acetato-κ²O,O')cobalt(II)]-µ- 4,4'-bis(benzimidazol-1-yl)biphenyl-κ²N³:N^3'] top

Crystal data top

[Co(C₂H₃O₂)₂(C₂₆H₁₈N₄)]	D_x = 1.542 Mg m⁻³
M_r = 563.46	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 6002 reflections
a = 13.078 (3) Å	θ = 2.0–27.9°
b = 16.348 (3) Å	µ = 0.75 mm⁻¹
c = 11.354 (2) Å	T = 293 K
V = 2427.5 (8) Å³	Block, purple
Z = 4	0.25 × 0.22 × 0.18 mm
F(000) = 1164

Data collection top

Rigaku CCD area-detector diffractometer	2150 independent reflections
Radiation source: fine-focus sealed tube	2101 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 2.7°
ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −19→19
T_min = 0.828, T_max = 0.873	l = −13→13
21778 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0367P)² + 2.7447P] where P = (F_o² + 2F_c²)/3
2150 reflections	(Δ/σ)_max < 0.001
178 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Co(C₂H₃O₂)₂(C₂₆H₁₈N₄)]	V = 2427.5 (8) Å³
M_r = 563.46	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 13.078 (3) Å	µ = 0.75 mm⁻¹
b = 16.348 (3) Å	T = 293 K
c = 11.354 (2) Å	0.25 × 0.22 × 0.18 mm

Data collection top

Rigaku CCD area-detector diffractometer	2150 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2101 reflections with I > 2σ(I)
T_min = 0.828, T_max = 0.873	R_int = 0.038
21778 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.10	Δρ_max = 0.27 e Å⁻³
2150 reflections	Δρ_min = −0.41 e Å⁻³
178 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
Co1	0.0000	0.40968 (2)	0.2500	0.01345 (14)
O1	0.08394 (11)	0.37040 (10)	0.39033 (14)	0.0268 (4)
C11	0.45996 (14)	0.51680 (12)	−0.20359 (17)	0.0138 (4)
C12	0.44299 (15)	0.44856 (12)	−0.13277 (18)	0.0160 (4)
H12	0.4800	0.4009	−0.1461	0.019*
C7	0.23045 (15)	0.58691 (12)	0.15147 (17)	0.0134 (4)
C3	0.11760 (15)	0.61095 (13)	0.31741 (17)	0.0163 (4)
H3	0.0633	0.5956	0.3655	0.020*
N2	0.24267 (12)	0.52419 (10)	0.06971 (14)	0.0140 (4)
N1	0.11225 (12)	0.48650 (10)	0.18429 (14)	0.0148 (4)
C10	0.40024 (15)	0.58655 (13)	−0.18495 (18)	0.0171 (4)
H10	0.4096	0.6322	−0.2327	0.021*
C13	0.37154 (15)	0.45080 (12)	−0.04256 (18)	0.0162 (4)
H13	0.3618	0.4054	0.0055	0.019*
C8	0.31481 (14)	0.52118 (12)	−0.02460 (17)	0.0144 (4)
C9	0.32729 (15)	0.58878 (12)	−0.09655 (18)	0.0164 (4)
H9	0.2872	0.6351	−0.0857	0.020*
C14	0.02557 (15)	0.31459 (12)	0.42490 (18)	0.0163 (4)
O2	−0.06065 (12)	0.30382 (10)	0.38106 (15)	0.0292 (4)
C4	0.17056 (15)	0.68295 (13)	0.33635 (18)	0.0184 (4)
H4	0.1517	0.7165	0.3989	0.022*
C1	0.17101 (15)	0.46685 (12)	0.09472 (17)	0.0153 (4)
H1	0.1641	0.4184	0.0526	0.018*
C15	0.06315 (17)	0.25921 (14)	0.5229 (2)	0.0249 (5)
H15A	0.0636	0.2889	0.5958	0.037*
H15B	0.1312	0.2408	0.5052	0.037*
H15C	0.0185	0.2128	0.5297	0.037*
C2	0.14891 (15)	0.56223 (12)	0.22333 (17)	0.0140 (4)
C6	0.28339 (15)	0.65947 (12)	0.16999 (17)	0.0162 (4)
H6	0.3372	0.6753	0.1216	0.019*
C5	0.25205 (16)	0.70673 (13)	0.26368 (18)	0.0176 (4)
H5	0.2858	0.7557	0.2792	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0112 (2)	0.0150 (2)	0.0141 (2)	0.000	0.00353 (14)	0.000
O1	0.0208 (8)	0.0286 (9)	0.0311 (9)	−0.0010 (7)	0.0001 (7)	0.0116 (7)
C11	0.0112 (9)	0.0182 (11)	0.0121 (9)	−0.0018 (8)	0.0014 (8)	−0.0006 (8)
C12	0.0148 (10)	0.0151 (10)	0.0182 (10)	0.0020 (8)	0.0026 (8)	−0.0013 (8)
C7	0.0132 (10)	0.0144 (10)	0.0126 (9)	0.0016 (7)	0.0007 (8)	0.0005 (8)
C3	0.0146 (10)	0.0214 (11)	0.0131 (10)	0.0008 (8)	0.0029 (8)	0.0006 (8)
N2	0.0134 (8)	0.0153 (8)	0.0133 (8)	−0.0009 (6)	0.0049 (7)	−0.0002 (7)
N1	0.0145 (8)	0.0154 (9)	0.0146 (8)	−0.0018 (7)	0.0037 (7)	−0.0016 (7)
C10	0.0173 (10)	0.0173 (11)	0.0167 (10)	0.0001 (8)	0.0041 (8)	0.0032 (8)
C13	0.0176 (10)	0.0144 (10)	0.0166 (10)	−0.0023 (8)	0.0035 (8)	0.0012 (8)
C8	0.0109 (9)	0.0189 (10)	0.0135 (10)	−0.0017 (8)	0.0042 (8)	−0.0012 (8)
C9	0.0141 (10)	0.0166 (10)	0.0184 (10)	0.0031 (8)	0.0036 (8)	0.0001 (8)
C14	0.0138 (10)	0.0187 (10)	0.0165 (10)	0.0023 (8)	0.0040 (8)	−0.0055 (8)
O2	0.0279 (9)	0.0226 (8)	0.0372 (9)	−0.0004 (7)	−0.0079 (8)	−0.0027 (7)
C4	0.0200 (11)	0.0197 (11)	0.0154 (10)	0.0025 (8)	0.0005 (8)	−0.0043 (8)
C1	0.0139 (10)	0.0159 (10)	0.0162 (10)	−0.0007 (8)	0.0038 (8)	−0.0009 (8)
C15	0.0237 (12)	0.0244 (12)	0.0265 (12)	0.0012 (9)	0.0015 (9)	0.0031 (10)
C2	0.0126 (9)	0.0151 (10)	0.0144 (10)	0.0010 (8)	0.0004 (8)	0.0007 (8)
C6	0.0129 (9)	0.0176 (10)	0.0180 (10)	−0.0015 (8)	0.0020 (8)	0.0019 (8)
C5	0.0162 (10)	0.0147 (10)	0.0220 (11)	−0.0014 (8)	−0.0022 (8)	−0.0016 (8)

Geometric parameters (Å, º) top

Co1—O1ⁱ	2.0386 (16)	N1—C1	1.315 (3)
Co1—O1	2.0386 (16)	N1—C2	1.400 (3)
Co1—O2	2.4163 (18)	C10—C9	1.385 (3)
Co1—O2ⁱ	2.4163 (18)	C10—H10	0.9300
Co1—N1	2.0709 (16)	C13—C8	1.384 (3)
Co1—N1ⁱ	2.0709 (16)	C13—H13	0.9300
O1—C14	1.253 (3)	C8—C9	1.384 (3)
C11—C12	1.393 (3)	C9—H9	0.9300
C11—C10	1.398 (3)	C14—O2	1.245 (3)
C11—C11ⁱⁱ	1.486 (4)	C14—C15	1.516 (3)
C12—C13	1.387 (3)	C4—C5	1.403 (3)
C12—H12	0.9300	C4—H4	0.9300
C7—C6	1.390 (3)	C1—H1	0.9300
C7—N2	1.392 (2)	C15—H15A	0.9600
C7—C2	1.402 (3)	C15—H15B	0.9600
C3—C4	1.383 (3)	C15—H15C	0.9600
C3—C2	1.394 (3)	C6—C5	1.377 (3)
C3—H3	0.9300	C6—H6	0.9300
N2—C1	1.356 (3)	C5—H5	0.9300
N2—C8	1.428 (2)

O1ⁱ—Co1—O1	143.29 (10)	C9—C8—C13	120.90 (18)
O1ⁱ—Co1—N1	106.93 (7)	C9—C8—N2	119.55 (17)
O1—Co1—N1	95.21 (6)	C13—C8—N2	119.55 (17)
O1ⁱ—Co1—N1ⁱ	95.21 (6)	C8—C9—C10	119.21 (18)
O1—Co1—N1ⁱ	106.93 (7)	C8—C9—H9	120.4
N1—Co1—N1ⁱ	105.34 (9)	C10—C9—H9	120.4
C14—O1—Co1	98.41 (13)	O2—C14—O1	122.0 (2)
C12—C11—C10	118.47 (18)	O2—C14—C15	120.16 (19)
C12—C11—C11ⁱⁱ	121.45 (13)	O1—C14—C15	117.86 (18)
C10—C11—C11ⁱⁱ	120.07 (13)	C3—C4—C5	121.67 (19)
C13—C12—C11	120.84 (18)	C3—C4—H4	119.2
C13—C12—H12	119.6	C5—C4—H4	119.2
C11—C12—H12	119.6	N1—C1—N2	113.41 (18)
C6—C7—N2	132.25 (18)	N1—C1—H1	123.3
C6—C7—C2	122.45 (18)	N2—C1—H1	123.3
N2—C7—C2	105.27 (17)	C14—C15—H15A	109.5
C4—C3—C2	117.29 (18)	C14—C15—H15B	109.5
C4—C3—H3	121.4	H15A—C15—H15B	109.5
C2—C3—H3	121.4	C14—C15—H15C	109.5
C1—N2—C7	106.87 (16)	H15A—C15—H15C	109.5
C1—N2—C8	126.16 (17)	H15B—C15—H15C	109.5
C7—N2—C8	126.95 (16)	C3—C2—N1	130.35 (18)
C1—N1—C2	105.12 (16)	C3—C2—C7	120.32 (19)
C1—N1—Co1	123.02 (14)	N1—C2—C7	109.32 (17)
C2—N1—Co1	131.69 (13)	C5—C6—C7	116.59 (18)
C9—C10—C11	121.05 (19)	C5—C6—H6	121.7
C9—C10—H10	119.5	C7—C6—H6	121.7
C11—C10—H10	119.5	C6—C5—C4	121.67 (19)
C8—C13—C12	119.46 (18)	C6—C5—H5	119.2
C8—C13—H13	120.3	C4—C5—H5	119.2
C12—C13—H13	120.3

O1ⁱ—Co1—O1—C14	−43.39 (12)	C13—C8—C9—C10	−2.3 (3)
N1—Co1—O1—C14	−171.08 (13)	N2—C8—C9—C10	177.49 (18)
N1ⁱ—Co1—O1—C14	81.14 (14)	C11—C10—C9—C8	1.1 (3)
C10—C11—C12—C13	−2.7 (3)	Co1—O1—C14—O2	−6.9 (2)
C11ⁱⁱ—C11—C12—C13	176.7 (2)	Co1—O1—C14—C15	172.84 (15)
C6—C7—N2—C1	178.2 (2)	C2—C3—C4—C5	0.5 (3)
C2—C7—N2—C1	0.0 (2)	C2—N1—C1—N2	−1.1 (2)
C6—C7—N2—C8	−3.3 (3)	Co1—N1—C1—N2	−176.94 (13)
C2—C7—N2—C8	178.53 (18)	C7—N2—C1—N1	0.7 (2)
O1ⁱ—Co1—N1—C1	−49.07 (17)	C8—N2—C1—N1	−177.81 (17)
O1—Co1—N1—C1	101.29 (16)	C4—C3—C2—N1	178.6 (2)
N1ⁱ—Co1—N1—C1	−149.55 (18)	C4—C3—C2—C7	−0.5 (3)
O1ⁱ—Co1—N1—C2	136.34 (17)	C1—N1—C2—C3	−178.1 (2)
O1—Co1—N1—C2	−73.29 (18)	Co1—N1—C2—C3	−2.8 (3)
N1ⁱ—Co1—N1—C2	35.86 (15)	C1—N1—C2—C7	1.1 (2)
C12—C11—C10—C9	1.4 (3)	Co1—N1—C2—C7	176.39 (13)
C11ⁱⁱ—C11—C10—C9	−178.0 (2)	C6—C7—C2—C3	0.2 (3)
C11—C12—C13—C8	1.5 (3)	N2—C7—C2—C3	178.57 (17)
C12—C13—C8—C9	1.0 (3)	C6—C7—C2—N1	−179.06 (18)
C12—C13—C8—N2	−178.74 (17)	N2—C7—C2—N1	−0.7 (2)
C1—N2—C8—C9	131.6 (2)	N2—C7—C6—C5	−177.7 (2)
C7—N2—C8—C9	−46.6 (3)	C2—C7—C6—C5	0.2 (3)
C1—N2—C8—C13	−48.6 (3)	C7—C6—C5—C4	−0.3 (3)
C7—N2—C8—C13	133.1 (2)	C3—C4—C5—C6	−0.1 (3)

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

Experimental details

Crystal data
Chemical formula	[Co(C₂H₃O₂)₂(C₂₆H₁₈N₄)]
M_r	563.46
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	13.078 (3), 16.348 (3), 11.354 (2)
V (Å³)	2427.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.25 × 0.22 × 0.18

Data collection
Diffractometer	Rigaku CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.828, 0.873
No. of measured, independent and observed [I > 2σ(I)] reflections	21778, 2150, 2101
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.083, 1.10
No. of reflections	2150
No. of parameters	178
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.41

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O1	2.0386 (16)	Co1—N1	2.0709 (16)
Co1—O2	2.4163 (18)

References

Jin, C. M., Lu, H., Wu, L. Y. & Huang, J. (2006). Chem. Commun. pp. 5039–5041. Web of Science CSD CrossRef Google Scholar
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