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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1207.
Published online 2010 September 4. doi:  10.1107/S1600536810034409
PMCID: PMC2983315

Dichloridobis[2-(2-fur­yl)-1-(2-furylmeth­yl)-1H-benzimidazole-κN 3]cadmium(II)

Abstract

In the title complex, [CdCl2(C16H12N2O2)2], the CdII ion exhibits site symmetry 2. It shows a distorted tetra­hedral coordination defined by two N atoms from symmetry-related 2-(2-fur­yl)-1-(2-furylmeth­yl)-1H-benzimidazole ligands and by two symmetry-related Cl atoms. Intra­molecular C—H(...)O hydrogen bonds stabilize the mol­ecular configuration. Adjacent mol­ecules are linked through C—H(...)Cl hydrogen bonds into a network structure.

Related literature

For background to benzimidazoles, see: Shen & Yuan (2006 [triangle]); Yang et al. (2008 [triangle]). For background to CdII complexes, see: Meng et al. (2004 [triangle]); Yang et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1207-scheme1.jpg

Experimental

Crystal data

  • [CdCl2(C16H12N2O2)2]
  • M r = 711.85
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1207-efi1.jpg
  • a = 18.397 (4) Å
  • b = 10.451 (2) Å
  • c = 17.470 (3) Å
  • β = 116.72 (3)°
  • V = 3000.2 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.95 mm−1
  • T = 293 K
  • 0.21 × 0.19 × 0.16 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (REQAB; Jacobson, 1998 [triangle]) T min = 0.825, T max = 0.863
  • 10628 measured reflections
  • 2953 independent reflections
  • 2565 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.110
  • S = 1.10
  • 2953 reflections
  • 195 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.47 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034409/wm2393sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034409/wm2393Isup2.hkl

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

Acknowledgments

The study was supported by the Science and Technology Department of Henan Province (082102330003).

supplementary crystallographic information

Comment

Benzimidazole and its derivatives have attracted interest because of their biological activities as well as their abilities to bind to different metal ions (Shen & Yuan, 2006; Yang et al., 2008). The CdII ion is a good model atom to construct complexes owing to its property to form bonds with different donors simultaneously, and to its various coordination modes (Meng et al., 2004; Yang et al., 2010). In this work, we describe the synthesis and structure of the title complex, [CdCl2(C16H12N2O2)2], (I).

In the structure of (I), two 2-(furan-2-yl)-1-(furan-2-yl-methyl)-1H-1,3-benzimidazole ligands and two Cl atoms coordinate to the CdII ion which is located on a twofold rotation axis. As expected, the Cd—Cl bond length is slightly longer than the Cd—N bond length. The environment around the CdII ion can be best described as distorted tetrahedral (Fig.1).

Intramolecular C—H···O hydrogen bonds stabilize the molecular configuration and C—H···Cl hydrogen bonds between adjacent molecules consolidate the crystal packing.

Experimental

The ligand 2-(furan-2-yl)-1-(furan-2-yl-methyl)-1H-1,3-benzimidazole (0.04 mmol) in methanol (7 ml) was added dropwise to a methanol solution (5 ml) of CdCl2 (0.02 mmol). The resulting solution was allowed to stand at room temperature. After one week colorless crystals with good quality were obtained from the filtrate and dried in air.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C-H = 0.93 (aromatic) and 0.97 (CH2) Å and with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
View of the title complex, showing the labelled atoms and displacement ellipsoids at the 30% probability level. H atoms were omitted for clarity. [Symmetry code A: -x+1, y, -z+0.5.]

Crystal data

[CdCl2(C16H12N2O2)2]F(000) = 1432
Mr = 711.85Dx = 1.576 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4133 reflections
a = 18.397 (4) Åθ = 2.3–27.9°
b = 10.451 (2) ŵ = 0.95 mm1
c = 17.470 (3) ÅT = 293 K
β = 116.72 (3)°Prism, colorless
V = 3000.2 (13) Å30.21 × 0.19 × 0.16 mm
Z = 4

Data collection

Rigaku Saturn diffractometer2953 independent reflections
Radiation source: fine-focus sealed tube2565 reflections with I > 2σ(I)
graphiteRint = 0.039
Detector resolution: 28.5714 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = −22→22
Absorption correction: multi-scan (REQAB; Jacobson, 1998)k = −12→10
Tmin = 0.825, Tmax = 0.863l = −21→21
10628 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0536P)2] where P = (Fo2 + 2Fc2)/3
2953 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.47 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
Cd10.5000−0.08924 (3)0.25000.04422 (17)
Cl10.61483 (7)−0.22781 (11)0.27047 (8)0.0670 (3)
O10.6047 (2)0.1489 (3)0.2577 (2)0.0742 (9)
O20.3968 (2)0.4328 (3)0.0331 (2)0.0822 (11)
N10.46860 (17)0.0215 (3)0.12856 (19)0.0401 (7)
N20.46152 (18)0.1695 (3)0.0334 (2)0.0439 (7)
C10.4133 (2)−0.0189 (3)0.0476 (2)0.0400 (9)
C20.3666 (2)−0.1304 (4)0.0213 (3)0.0487 (10)
H2A0.3693−0.19270.06050.058*
C30.3166 (2)−0.1443 (4)−0.0649 (3)0.0552 (11)
H3A0.2846−0.2173−0.08420.066*
C40.3126 (3)−0.0521 (5)−0.1240 (3)0.0613 (12)
H4A0.2782−0.0653−0.18180.074*
C50.3582 (3)0.0584 (4)−0.0994 (3)0.0541 (11)
H5A0.35560.1202−0.13880.065*
C60.4083 (2)0.0723 (3)−0.0121 (3)0.0426 (9)
C70.4950 (2)0.1349 (3)0.1171 (2)0.0407 (8)
C80.5529 (2)0.2124 (4)0.1863 (3)0.0476 (9)
C90.5623 (3)0.3387 (4)0.1971 (3)0.0574 (11)
H9A0.53300.40160.15760.069*
C100.6258 (3)0.3579 (6)0.2805 (4)0.0835 (17)
H10A0.64690.43630.30600.100*
C110.6496 (3)0.2440 (7)0.3154 (3)0.0882 (17)
H11A0.69050.22940.37050.106*
C120.4755 (2)0.2850 (4)−0.0060 (3)0.0520 (10)
H12A0.48170.2609−0.05640.062*
H12B0.52570.32540.03420.062*
C130.4077 (3)0.3782 (4)−0.0311 (3)0.0532 (11)
C140.3522 (3)0.4196 (4)−0.1061 (3)0.0719 (14)
H14A0.34730.3972−0.15970.086*
C150.3012 (3)0.5054 (5)−0.0888 (4)0.0888 (19)
H15A0.25640.5498−0.12900.107*
C160.3296 (4)0.5097 (5)−0.0057 (5)0.097 (2)
H16A0.30730.55810.02320.117*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.0472 (3)0.0419 (3)0.0376 (2)0.0000.01378 (19)0.000
Cl10.0685 (7)0.0712 (8)0.0582 (7)0.0256 (6)0.0256 (6)0.0060 (6)
O10.076 (2)0.082 (2)0.057 (2)0.0048 (19)0.0234 (18)0.0035 (18)
O20.103 (3)0.079 (2)0.077 (2)0.046 (2)0.052 (2)0.0202 (18)
N10.0410 (17)0.0379 (18)0.0373 (17)0.0028 (14)0.0141 (14)0.0035 (13)
N20.0451 (18)0.0402 (18)0.0467 (19)0.0071 (15)0.0209 (15)0.0041 (15)
C10.037 (2)0.042 (2)0.038 (2)0.0097 (16)0.0150 (17)0.0002 (16)
C20.044 (2)0.047 (2)0.053 (2)0.0025 (18)0.0194 (19)−0.0037 (19)
C30.046 (2)0.061 (3)0.050 (3)0.001 (2)0.013 (2)−0.017 (2)
C40.053 (3)0.076 (3)0.038 (2)0.012 (2)0.006 (2)−0.010 (2)
C50.053 (3)0.065 (3)0.042 (2)0.018 (2)0.019 (2)0.008 (2)
C60.040 (2)0.045 (2)0.042 (2)0.0131 (17)0.0170 (17)0.0022 (17)
C70.040 (2)0.039 (2)0.041 (2)0.0060 (17)0.0168 (17)0.0031 (16)
C80.043 (2)0.052 (2)0.049 (2)−0.0006 (19)0.0220 (19)0.0009 (19)
C90.062 (3)0.040 (2)0.063 (3)−0.012 (2)0.021 (2)−0.003 (2)
C100.080 (4)0.085 (4)0.084 (4)−0.045 (3)0.035 (3)−0.037 (3)
C110.060 (3)0.134 (5)0.056 (3)−0.006 (4)0.013 (3)−0.018 (4)
C120.057 (3)0.049 (2)0.057 (3)0.0098 (19)0.033 (2)0.0160 (19)
C130.059 (3)0.040 (2)0.065 (3)0.0088 (19)0.031 (2)0.009 (2)
C140.079 (4)0.052 (3)0.066 (3)0.014 (2)0.016 (3)0.002 (2)
C150.074 (4)0.051 (3)0.111 (5)0.021 (3)0.015 (4)0.008 (3)
C160.099 (5)0.077 (4)0.125 (6)0.045 (3)0.059 (4)0.012 (4)

Geometric parameters (Å, °)

Cd1—N1i2.252 (3)C4—H4A0.9300
Cd1—N12.252 (3)C5—C61.389 (5)
Cd1—Cl1i2.4513 (12)C5—H5A0.9300
Cd1—Cl12.4513 (12)C7—C81.447 (5)
O1—C81.354 (5)C8—C91.334 (5)
O1—C111.392 (6)C9—C101.414 (7)
O2—C131.352 (5)C9—H9A0.9300
O2—C161.372 (6)C10—C111.319 (7)
N1—C71.330 (5)C10—H10A0.9300
N1—C11.386 (4)C11—H11A0.9300
N2—C71.356 (5)C12—C131.484 (5)
N2—C61.387 (5)C12—H12A0.9700
N2—C121.469 (5)C12—H12B0.9700
C1—C61.386 (5)C13—C141.320 (6)
C1—C21.396 (5)C14—C151.424 (7)
C2—C31.374 (6)C14—H14A0.9300
C2—H2A0.9300C15—C161.305 (8)
C3—C41.390 (6)C15—H15A0.9300
C3—H3A0.9300C16—H16A0.9300
C4—C51.378 (6)
N1i—Cd1—N1118.17 (15)N1—C7—C8123.6 (3)
N1i—Cd1—Cl1i106.27 (8)N2—C7—C8124.0 (3)
N1—Cd1—Cl1i109.08 (8)C9—C8—O1111.2 (4)
N1i—Cd1—Cl1109.08 (8)C9—C8—C7132.2 (4)
N1—Cd1—Cl1106.27 (8)O1—C8—C7116.4 (4)
Cl1i—Cd1—Cl1107.57 (6)C8—C9—C10106.3 (4)
C8—O1—C11105.1 (4)C8—C9—H9A126.8
C13—O2—C16105.9 (4)C10—C9—H9A126.8
C7—N1—C1105.5 (3)C11—C10—C9107.3 (4)
C7—N1—Cd1130.1 (2)C11—C10—H10A126.4
C1—N1—Cd1124.4 (2)C9—C10—H10A126.4
C7—N2—C6106.5 (3)C10—C11—O1110.1 (5)
C7—N2—C12129.4 (3)C10—C11—H11A125.0
C6—N2—C12124.1 (3)O1—C11—H11A125.0
N1—C1—C6109.2 (3)N2—C12—C13112.1 (3)
N1—C1—C2130.6 (4)N2—C12—H12A109.2
C6—C1—C2120.2 (4)C13—C12—H12A109.2
C3—C2—C1117.3 (4)N2—C12—H12B109.2
C3—C2—H2A121.4C13—C12—H12B109.2
C1—C2—H2A121.4H12A—C12—H12B107.9
C2—C3—C4121.8 (4)C14—C13—O2110.3 (4)
C2—C3—H3A119.1C14—C13—C12133.0 (5)
C4—C3—H3A119.1O2—C13—C12116.7 (4)
C3—C4—C5121.8 (4)C13—C14—C15106.7 (5)
C3—C4—H4A119.1C13—C14—H14A126.7
C5—C4—H4A119.1C15—C14—H14A126.7
C4—C5—C6116.2 (4)C16—C15—C14106.5 (5)
C4—C5—H5A121.9C16—C15—H15A126.7
C6—C5—H5A121.9C14—C15—H15A126.7
N2—C6—C1106.3 (3)C15—C16—O2110.5 (5)
N2—C6—C5130.9 (4)C15—C16—H16A124.7
C1—C6—C5122.7 (4)O2—C16—H16A124.7
N1—C7—N2112.4 (3)
N1i—Cd1—N1—C731.3 (3)Cd1—N1—C7—C8−0.1 (5)
Cl1i—Cd1—N1—C7152.8 (3)C6—N2—C7—N11.3 (4)
Cl1—Cd1—N1—C7−91.5 (3)C12—N2—C7—N1−178.8 (3)
N1i—Cd1—N1—C1−147.1 (3)C6—N2—C7—C8−178.6 (4)
Cl1i—Cd1—N1—C1−25.7 (3)C12—N2—C7—C81.3 (6)
Cl1—Cd1—N1—C190.0 (3)C11—O1—C8—C9−0.9 (5)
C7—N1—C1—C60.8 (4)C11—O1—C8—C7−176.4 (4)
Cd1—N1—C1—C6179.6 (2)N1—C7—C8—C9−147.9 (5)
C7—N1—C1—C2−179.6 (4)N2—C7—C8—C932.1 (7)
Cd1—N1—C1—C2−0.8 (5)N1—C7—C8—O126.4 (6)
N1—C1—C2—C3−179.7 (4)N2—C7—C8—O1−153.6 (4)
C6—C1—C2—C3−0.2 (5)O1—C8—C9—C101.3 (5)
C1—C2—C3—C40.4 (6)C7—C8—C9—C10175.8 (5)
C2—C3—C4—C5−0.3 (7)C8—C9—C10—C11−1.2 (6)
C3—C4—C5—C60.0 (6)C9—C10—C11—O10.6 (7)
C7—N2—C6—C1−0.7 (4)C8—O1—C11—C100.1 (6)
C12—N2—C6—C1179.4 (3)C7—N2—C12—C13−103.6 (5)
C7—N2—C6—C5179.8 (4)C6—N2—C12—C1376.2 (5)
C12—N2—C6—C5−0.1 (6)C16—O2—C13—C141.3 (6)
N1—C1—C6—N20.0 (4)C16—O2—C13—C12−177.5 (4)
C2—C1—C6—N2−179.7 (3)N2—C12—C13—C14−112.3 (6)
N1—C1—C6—C5179.5 (3)N2—C12—C13—O266.1 (5)
C2—C1—C6—C5−0.1 (6)O2—C13—C14—C15−0.9 (6)
C4—C5—C6—N2179.6 (4)C12—C13—C14—C15177.6 (5)
C4—C5—C6—C10.2 (6)C13—C14—C15—C160.2 (7)
C1—N1—C7—N2−1.3 (4)C14—C15—C16—O20.6 (7)
Cd1—N1—C7—N2180.0 (2)C13—O2—C16—C15−1.2 (7)
C1—N1—C7—C8178.6 (4)

Symmetry codes: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5A···Cl1ii0.932.823.694 (5)156
C9—H9A···O20.932.493.256 (6)140

Symmetry codes: (ii) −x+1, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2393).

References

  • Jacobson, R. (1998). REQAB Private communication to the Rigaku Corporation, Tokyo, Japan.
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  • Rigaku/MSC (2006). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shen, X.-P. & Yuan, A.-H. (2006). Acta Cryst. E62, m2849–m2850.
  • Yang, H.-X., Meng, X.-R., Liu, Y., Hou, H.-W., Fan, Y.-T. & Shen, X.-Q. (2008). J. Solid State Chem.181, 2178–2184.
  • Yang, H.-X., Zhang, J., Ding, Y.-N. & Meng, X.-R. (2010). Acta Cryst. E66, m578. [PMC free article] [PubMed]

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