Literature DB >> 21587366

Dichloridobis[2-(2-fur-yl)-1-(2-furylmeth-yl)-1H-benzimidazole-κN]cadmium(II).

Xia Wang1, Yu-Xian Li, Yan-Ju Liu, Huai-Xia Yang, Cong-Cong Zhang.   

Abstract

In the title complex, [CdCl(2)(C(16)n class="Species">H(12)N(2)O(2))(2)], the Cd(II) ion exhibits site symmetry 2. It shows a distorted tetra-hedral coordination defined by two N atoms from symmetry-related 2-(2-fur-yl)-1-(2-furylmeth-yl)-1H-benzimidazole ligands and by two symmetry-related Cl atoms. Intra-molecular C-H⋯O hydrogen bonds stabilize the mol-ecular configuration. Adjacent mol-ecules are linked through C-H⋯Cl hydrogen bonds into a network structure.

Entities:  

Year:  2010        PMID： 21587366      PMCID： PMC2983315          DOI： 10.1107/S1600536810034409

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to benzimidazoles, see: Shen & Yuan (2006 ▶); Yang et al. (2008 ▶). For background to n class="Chemical">CdII complexes, see: Meng et al. (2004 ▶); Yang et al. (2010 ▶).

Experimental

Crystal data

[CdCl2(n class="CellLine">C16H12N2O2)2] M = 711.85 Monoclinic, 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 ▶) 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 ▶); 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. 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
[CdCl2(C16H12N2O2)2]F(000) = 1432
Mr = 711.85Dx = 1.576 Mg m−3
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 mm−1
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
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 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 Å−3
0 restraintsΔρmin = −0.47 e Å−3
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.
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*
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)
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)
D—H···AD—HH···AD···AD—H···A
C5—H5A···Cl1ii0.932.823.694 (5)156
C9—H9A···O20.932.493.256 (6)140
Cd1—N12.252 (3)
Cd1—Cl12.4513 (12)
N1i—Cd1—N1118.17 (15)
N1i—Cd1—Cl1109.08 (8)
N1—Cd1—Cl1106.27 (8)
Cl1i—Cd1—Cl1107.57 (6)

Symmetry code: (i) .

Table 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 code: (ii) .

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