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

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

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 CoII 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 CoII 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[Jin, C. M., Lu, H., Wu, L. Y. & Huang, J. (2006). Chem. Commun. pp. 5039-5041.]); Li et al. (2010[Li, Z. X., Hu, T. L., Ma, H., Zeng, Y. F., Li, C. J., Tong, M. L. & Bu, X. H. (2010). Cryst. Growth Des. 10, 1138-1144.]); Su et al. (2003[Su, C. Y., Cai, Y. P., Chen, C. L., Smith, M. D., Kaim, W. & zur Loye, H. C. (2003). J. Am. Chem. Soc. 125, 8595-8613.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(C2H3O2)2(C26H18N4)]

  • Mr = 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.828, Tmax = 0.873

  • 21778 measured reflections

  • 2150 independent reflections

  • 2101 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.083

  • S = 1.10

  • 2150 reflections

  • 178 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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 CoII 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 CoII 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).

Refinement top

C-bound H atoms were positioned geometrically and refined in the riding-model approximation, with C—H = 0.93Å and Uiso(H) = 1.2Ueq.

Structure description 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 CoII 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 CoII center is bridged by the linear ligand L to form an infinite one-dimensional architecture.

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
[Figure 1] 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.
[Figure 2] Fig. 2. The crystal packing for (I).
catena-Poly[[bis(acetato-κ2O,O')cobalt(II)]-µ- 4,4'-bis(benzimidazol-1-yl)biphenyl-κ2N3:N3'] top
Crystal data top
[Co(C2H3O2)2(C26H18N4)]Dx = 1.542 Mg m3
Mr = 563.46Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 6002 reflections
a = 13.078 (3) Åθ = 2.0–27.9°
b = 16.348 (3) ŵ = 0.75 mm1
c = 11.354 (2) ÅT = 293 K
V = 2427.5 (8) Å3Block, purple
Z = 40.25 × 0.22 × 0.18 mm
F(000) = 1164
Data collection top
Rigaku CCD area-detector
diffractometer
2150 independent reflections
Radiation source: fine-focus sealed tube2101 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 2.7°
ω scansh = 1515
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1919
Tmin = 0.828, Tmax = 0.873l = 1313
21778 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0367P)2 + 2.7447P]
where P = (Fo2 + 2Fc2)/3
2150 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
[Co(C2H3O2)2(C26H18N4)]V = 2427.5 (8) Å3
Mr = 563.46Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 13.078 (3) ŵ = 0.75 mm1
b = 16.348 (3) ÅT = 293 K
c = 11.354 (2) Å0.25 × 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)
Tmin = 0.828, Tmax = 0.873Rint = 0.038
21778 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.083H-atom parameters constrained
S = 1.10Δρmax = 0.27 e Å3
2150 reflectionsΔρmin = 0.41 e Å3
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
xyzUiso*/Ueq
Co10.00000.40968 (2)0.25000.01345 (14)
O10.08394 (11)0.37040 (10)0.39033 (14)0.0268 (4)
C110.45996 (14)0.51680 (12)0.20359 (17)0.0138 (4)
C120.44299 (15)0.44856 (12)0.13277 (18)0.0160 (4)
H120.48000.40090.14610.019*
C70.23045 (15)0.58691 (12)0.15147 (17)0.0134 (4)
C30.11760 (15)0.61095 (13)0.31741 (17)0.0163 (4)
H30.06330.59560.36550.020*
N20.24267 (12)0.52419 (10)0.06971 (14)0.0140 (4)
N10.11225 (12)0.48650 (10)0.18429 (14)0.0148 (4)
C100.40024 (15)0.58655 (13)0.18495 (18)0.0171 (4)
H100.40960.63220.23270.021*
C130.37154 (15)0.45080 (12)0.04256 (18)0.0162 (4)
H130.36180.40540.00550.019*
C80.31481 (14)0.52118 (12)0.02460 (17)0.0144 (4)
C90.32729 (15)0.58878 (12)0.09655 (18)0.0164 (4)
H90.28720.63510.08570.020*
C140.02557 (15)0.31459 (12)0.42490 (18)0.0163 (4)
O20.06065 (12)0.30382 (10)0.38106 (15)0.0292 (4)
C40.17056 (15)0.68295 (13)0.33635 (18)0.0184 (4)
H40.15170.71650.39890.022*
C10.17101 (15)0.46685 (12)0.09472 (17)0.0153 (4)
H10.16410.41840.05260.018*
C150.06315 (17)0.25921 (14)0.5229 (2)0.0249 (5)
H15A0.06360.28890.59580.037*
H15B0.13120.24080.50520.037*
H15C0.01850.21280.52970.037*
C20.14891 (15)0.56223 (12)0.22333 (17)0.0140 (4)
C60.28339 (15)0.65947 (12)0.16999 (17)0.0162 (4)
H60.33720.67530.12160.019*
C50.25205 (16)0.70673 (13)0.26368 (18)0.0176 (4)
H50.28580.75570.27920.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0112 (2)0.0150 (2)0.0141 (2)0.0000.00353 (14)0.000
O10.0208 (8)0.0286 (9)0.0311 (9)0.0010 (7)0.0001 (7)0.0116 (7)
C110.0112 (9)0.0182 (11)0.0121 (9)0.0018 (8)0.0014 (8)0.0006 (8)
C120.0148 (10)0.0151 (10)0.0182 (10)0.0020 (8)0.0026 (8)0.0013 (8)
C70.0132 (10)0.0144 (10)0.0126 (9)0.0016 (7)0.0007 (8)0.0005 (8)
C30.0146 (10)0.0214 (11)0.0131 (10)0.0008 (8)0.0029 (8)0.0006 (8)
N20.0134 (8)0.0153 (8)0.0133 (8)0.0009 (6)0.0049 (7)0.0002 (7)
N10.0145 (8)0.0154 (9)0.0146 (8)0.0018 (7)0.0037 (7)0.0016 (7)
C100.0173 (10)0.0173 (11)0.0167 (10)0.0001 (8)0.0041 (8)0.0032 (8)
C130.0176 (10)0.0144 (10)0.0166 (10)0.0023 (8)0.0035 (8)0.0012 (8)
C80.0109 (9)0.0189 (10)0.0135 (10)0.0017 (8)0.0042 (8)0.0012 (8)
C90.0141 (10)0.0166 (10)0.0184 (10)0.0031 (8)0.0036 (8)0.0001 (8)
C140.0138 (10)0.0187 (10)0.0165 (10)0.0023 (8)0.0040 (8)0.0055 (8)
O20.0279 (9)0.0226 (8)0.0372 (9)0.0004 (7)0.0079 (8)0.0027 (7)
C40.0200 (11)0.0197 (11)0.0154 (10)0.0025 (8)0.0005 (8)0.0043 (8)
C10.0139 (10)0.0159 (10)0.0162 (10)0.0007 (8)0.0038 (8)0.0009 (8)
C150.0237 (12)0.0244 (12)0.0265 (12)0.0012 (9)0.0015 (9)0.0031 (10)
C20.0126 (9)0.0151 (10)0.0144 (10)0.0010 (8)0.0004 (8)0.0007 (8)
C60.0129 (9)0.0176 (10)0.0180 (10)0.0015 (8)0.0020 (8)0.0019 (8)
C50.0162 (10)0.0147 (10)0.0220 (11)0.0014 (8)0.0022 (8)0.0016 (8)
Geometric parameters (Å, º) top
Co1—O1i2.0386 (16)N1—C11.315 (3)
Co1—O12.0386 (16)N1—C21.400 (3)
Co1—O22.4163 (18)C10—C91.385 (3)
Co1—O2i2.4163 (18)C10—H100.9300
Co1—N12.0709 (16)C13—C81.384 (3)
Co1—N1i2.0709 (16)C13—H130.9300
O1—C141.253 (3)C8—C91.384 (3)
C11—C121.393 (3)C9—H90.9300
C11—C101.398 (3)C14—O21.245 (3)
C11—C11ii1.486 (4)C14—C151.516 (3)
C12—C131.387 (3)C4—C51.403 (3)
C12—H120.9300C4—H40.9300
C7—C61.390 (3)C1—H10.9300
C7—N21.392 (2)C15—H15A0.9600
C7—C21.402 (3)C15—H15B0.9600
C3—C41.383 (3)C15—H15C0.9600
C3—C21.394 (3)C6—C51.377 (3)
C3—H30.9300C6—H60.9300
N2—C11.356 (3)C5—H50.9300
N2—C81.428 (2)
O1i—Co1—O1143.29 (10)C9—C8—C13120.90 (18)
O1i—Co1—N1106.93 (7)C9—C8—N2119.55 (17)
O1—Co1—N195.21 (6)C13—C8—N2119.55 (17)
O1i—Co1—N1i95.21 (6)C8—C9—C10119.21 (18)
O1—Co1—N1i106.93 (7)C8—C9—H9120.4
N1—Co1—N1i105.34 (9)C10—C9—H9120.4
C14—O1—Co198.41 (13)O2—C14—O1122.0 (2)
C12—C11—C10118.47 (18)O2—C14—C15120.16 (19)
C12—C11—C11ii121.45 (13)O1—C14—C15117.86 (18)
C10—C11—C11ii120.07 (13)C3—C4—C5121.67 (19)
C13—C12—C11120.84 (18)C3—C4—H4119.2
C13—C12—H12119.6C5—C4—H4119.2
C11—C12—H12119.6N1—C1—N2113.41 (18)
C6—C7—N2132.25 (18)N1—C1—H1123.3
C6—C7—C2122.45 (18)N2—C1—H1123.3
N2—C7—C2105.27 (17)C14—C15—H15A109.5
C4—C3—C2117.29 (18)C14—C15—H15B109.5
C4—C3—H3121.4H15A—C15—H15B109.5
C2—C3—H3121.4C14—C15—H15C109.5
C1—N2—C7106.87 (16)H15A—C15—H15C109.5
C1—N2—C8126.16 (17)H15B—C15—H15C109.5
C7—N2—C8126.95 (16)C3—C2—N1130.35 (18)
C1—N1—C2105.12 (16)C3—C2—C7120.32 (19)
C1—N1—Co1123.02 (14)N1—C2—C7109.32 (17)
C2—N1—Co1131.69 (13)C5—C6—C7116.59 (18)
C9—C10—C11121.05 (19)C5—C6—H6121.7
C9—C10—H10119.5C7—C6—H6121.7
C11—C10—H10119.5C6—C5—C4121.67 (19)
C8—C13—C12119.46 (18)C6—C5—H5119.2
C8—C13—H13120.3C4—C5—H5119.2
C12—C13—H13120.3
O1i—Co1—O1—C1443.39 (12)C13—C8—C9—C102.3 (3)
N1—Co1—O1—C14171.08 (13)N2—C8—C9—C10177.49 (18)
N1i—Co1—O1—C1481.14 (14)C11—C10—C9—C81.1 (3)
C10—C11—C12—C132.7 (3)Co1—O1—C14—O26.9 (2)
C11ii—C11—C12—C13176.7 (2)Co1—O1—C14—C15172.84 (15)
C6—C7—N2—C1178.2 (2)C2—C3—C4—C50.5 (3)
C2—C7—N2—C10.0 (2)C2—N1—C1—N21.1 (2)
C6—C7—N2—C83.3 (3)Co1—N1—C1—N2176.94 (13)
C2—C7—N2—C8178.53 (18)C7—N2—C1—N10.7 (2)
O1i—Co1—N1—C149.07 (17)C8—N2—C1—N1177.81 (17)
O1—Co1—N1—C1101.29 (16)C4—C3—C2—N1178.6 (2)
N1i—Co1—N1—C1149.55 (18)C4—C3—C2—C70.5 (3)
O1i—Co1—N1—C2136.34 (17)C1—N1—C2—C3178.1 (2)
O1—Co1—N1—C273.29 (18)Co1—N1—C2—C32.8 (3)
N1i—Co1—N1—C235.86 (15)C1—N1—C2—C71.1 (2)
C12—C11—C10—C91.4 (3)Co1—N1—C2—C7176.39 (13)
C11ii—C11—C10—C9178.0 (2)C6—C7—C2—C30.2 (3)
C11—C12—C13—C81.5 (3)N2—C7—C2—C3178.57 (17)
C12—C13—C8—C91.0 (3)C6—C7—C2—N1179.06 (18)
C12—C13—C8—N2178.74 (17)N2—C7—C2—N10.7 (2)
C1—N2—C8—C9131.6 (2)N2—C7—C6—C5177.7 (2)
C7—N2—C8—C946.6 (3)C2—C7—C6—C50.2 (3)
C1—N2—C8—C1348.6 (3)C7—C6—C5—C40.3 (3)
C7—N2—C8—C13133.1 (2)C3—C4—C5—C60.1 (3)
Symmetry codes: (i) x, y, z+1/2; (ii) x+1, y, z1/2.

Experimental details

Crystal data
Chemical formula[Co(C2H3O2)2(C26H18N4)]
Mr563.46
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)293
a, b, c (Å)13.078 (3), 16.348 (3), 11.354 (2)
V3)2427.5 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.75
Crystal size (mm)0.25 × 0.22 × 0.18
Data collection
DiffractometerRigaku CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.828, 0.873
No. of measured, independent and
observed [I > 2σ(I)] reflections
21778, 2150, 2101
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.083, 1.10
No. of reflections2150
No. of parameters178
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—O12.0386 (16)Co1—N12.0709 (16)
Co1—O22.4163 (18)
 

References

First citationJin, C. M., Lu, H., Wu, L. Y. & Huang, J. (2006). Chem. Commun. pp. 5039–5041.  Web of Science CSD CrossRef Google Scholar
First citationLi, Z. X., Hu, T. L., Ma, H., Zeng, Y. F., Li, C. J., Tong, M. L. & Bu, X. H. (2010). Cryst. Growth Des. 10, 1138–1144.  Web of Science CSD CrossRef CAS Google Scholar
First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSu, C. Y., Cai, Y. P., Chen, C. L., Smith, M. D., Kaim, W. & zur Loye, H. C. (2003). J. Am. Chem. Soc. 125, 8595–8613.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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