Experimental
Crystal data
[CdCl2(C16H12N2O2)2] Mr = 711.85 Monoclinic, C 2/c 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 ) Tmin = 0.825, Tmax = 0.863 10628 measured reflections 2953 independent reflections 2565 reflections with I > 2σ(I) Rint = 0.039
|
Cd1—N1 | 2.252 (3) | Cd1—Cl1 | 2.4513 (12) | | N1i—Cd1—N1 | 118.17 (15) | N1i—Cd1—Cl1 | 109.08 (8) | N1—Cd1—Cl1 | 106.27 (8) | Cl1i—Cd1—Cl1 | 107.57 (6) | Symmetry code: (i) . | |
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | C5—H5A⋯Cl1ii | 0.93 | 2.82 | 3.694 (5) | 156 | C9—H9A⋯O2 | 0.93 | 2.49 | 3.256 (6) | 140 | Symmetry code: (ii) -x+1, -y, -z. | |
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.
Supporting information
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.
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).
Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXL97 (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 (Sheldrick, 2008).
Dichloridobis[2-(2-furyl)-1-(2-furylmethyl)-1
H-benzimidazole-
κN3]cadmium(II)
top Crystal data top [CdCl2(C16H12N2O2)2] | F(000) = 1432 |
Mr = 711.85 | Dx = 1.576 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4133 reflections |
a = 18.397 (4) Å | θ = 2.3–27.9° |
b = 10.451 (2) Å | µ = 0.95 mm−1 |
c = 17.470 (3) Å | T = 293 K |
β = 116.72 (3)° | Prism, colorless |
V = 3000.2 (13) Å3 | 0.21 × 0.19 × 0.16 mm |
Z = 4 | |
Data collection top Rigaku Saturn diffractometer | 2953 independent reflections |
Radiation source: fine-focus sealed tube | 2565 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 26.0°, θmin = 2.3° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (REQAB; Jacobson, 1998) | k = −12→10 |
Tmin = 0.825, Tmax = 0.863 | l = −21→21 |
10628 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0536P)2] where P = (Fo2 + 2Fc2)/3 |
2953 reflections | (Δ/σ)max < 0.001 |
195 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
Crystal data top [CdCl2(C16H12N2O2)2] | V = 3000.2 (13) Å3 |
Mr = 711.85 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 18.397 (4) Å | µ = 0.95 mm−1 |
b = 10.451 (2) Å | T = 293 K |
c = 17.470 (3) Å | 0.21 × 0.19 × 0.16 mm |
β = 116.72 (3)° | |
Data collection top Rigaku Saturn diffractometer | 2953 independent reflections |
Absorption correction: multi-scan (REQAB; Jacobson, 1998) | 2565 reflections with I > 2σ(I) |
Tmin = 0.825, Tmax = 0.863 | Rint = 0.039 |
10628 measured reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.34 e Å−3 |
2953 reflections | Δρmin = −0.47 e Å−3 |
195 parameters | |
Special details top 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) top | x | y | z | Uiso*/Ueq | |
Cd1 | 0.5000 | −0.08924 (3) | 0.2500 | 0.04422 (17) | |
Cl1 | 0.61483 (7) | −0.22781 (11) | 0.27047 (8) | 0.0670 (3) | |
O1 | 0.6047 (2) | 0.1489 (3) | 0.2577 (2) | 0.0742 (9) | |
O2 | 0.3968 (2) | 0.4328 (3) | 0.0331 (2) | 0.0822 (11) | |
N1 | 0.46860 (17) | 0.0215 (3) | 0.12856 (19) | 0.0401 (7) | |
N2 | 0.46152 (18) | 0.1695 (3) | 0.0334 (2) | 0.0439 (7) | |
C1 | 0.4133 (2) | −0.0189 (3) | 0.0476 (2) | 0.0400 (9) | |
C2 | 0.3666 (2) | −0.1304 (4) | 0.0213 (3) | 0.0487 (10) | |
H2A | 0.3693 | −0.1927 | 0.0605 | 0.058* | |
C3 | 0.3166 (2) | −0.1443 (4) | −0.0649 (3) | 0.0552 (11) | |
H3A | 0.2846 | −0.2173 | −0.0842 | 0.066* | |
C4 | 0.3126 (3) | −0.0521 (5) | −0.1240 (3) | 0.0613 (12) | |
H4A | 0.2782 | −0.0653 | −0.1818 | 0.074* | |
C5 | 0.3582 (3) | 0.0584 (4) | −0.0994 (3) | 0.0541 (11) | |
H5A | 0.3556 | 0.1202 | −0.1388 | 0.065* | |
C6 | 0.4083 (2) | 0.0723 (3) | −0.0121 (3) | 0.0426 (9) | |
C7 | 0.4950 (2) | 0.1349 (3) | 0.1171 (2) | 0.0407 (8) | |
C8 | 0.5529 (2) | 0.2124 (4) | 0.1863 (3) | 0.0476 (9) | |
C9 | 0.5623 (3) | 0.3387 (4) | 0.1971 (3) | 0.0574 (11) | |
H9A | 0.5330 | 0.4016 | 0.1576 | 0.069* | |
C10 | 0.6258 (3) | 0.3579 (6) | 0.2805 (4) | 0.0835 (17) | |
H10A | 0.6469 | 0.4363 | 0.3060 | 0.100* | |
C11 | 0.6496 (3) | 0.2440 (7) | 0.3154 (3) | 0.0882 (17) | |
H11A | 0.6905 | 0.2294 | 0.3705 | 0.106* | |
C12 | 0.4755 (2) | 0.2850 (4) | −0.0060 (3) | 0.0520 (10) | |
H12A | 0.4817 | 0.2609 | −0.0564 | 0.062* | |
H12B | 0.5257 | 0.3254 | 0.0342 | 0.062* | |
C13 | 0.4077 (3) | 0.3782 (4) | −0.0311 (3) | 0.0532 (11) | |
C14 | 0.3522 (3) | 0.4196 (4) | −0.1061 (3) | 0.0719 (14) | |
H14A | 0.3473 | 0.3972 | −0.1597 | 0.086* | |
C15 | 0.3012 (3) | 0.5054 (5) | −0.0888 (4) | 0.0888 (19) | |
H15A | 0.2564 | 0.5498 | −0.1290 | 0.107* | |
C16 | 0.3296 (4) | 0.5097 (5) | −0.0057 (5) | 0.097 (2) | |
H16A | 0.3073 | 0.5581 | 0.0232 | 0.117* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.0472 (3) | 0.0419 (3) | 0.0376 (2) | 0.000 | 0.01378 (19) | 0.000 |
Cl1 | 0.0685 (7) | 0.0712 (8) | 0.0582 (7) | 0.0256 (6) | 0.0256 (6) | 0.0060 (6) |
O1 | 0.076 (2) | 0.082 (2) | 0.057 (2) | 0.0048 (19) | 0.0234 (18) | 0.0035 (18) |
O2 | 0.103 (3) | 0.079 (2) | 0.077 (2) | 0.046 (2) | 0.052 (2) | 0.0202 (18) |
N1 | 0.0410 (17) | 0.0379 (18) | 0.0373 (17) | 0.0028 (14) | 0.0141 (14) | 0.0035 (13) |
N2 | 0.0451 (18) | 0.0402 (18) | 0.0467 (19) | 0.0071 (15) | 0.0209 (15) | 0.0041 (15) |
C1 | 0.037 (2) | 0.042 (2) | 0.038 (2) | 0.0097 (16) | 0.0150 (17) | 0.0002 (16) |
C2 | 0.044 (2) | 0.047 (2) | 0.053 (2) | 0.0025 (18) | 0.0194 (19) | −0.0037 (19) |
C3 | 0.046 (2) | 0.061 (3) | 0.050 (3) | 0.001 (2) | 0.013 (2) | −0.017 (2) |
C4 | 0.053 (3) | 0.076 (3) | 0.038 (2) | 0.012 (2) | 0.006 (2) | −0.010 (2) |
C5 | 0.053 (3) | 0.065 (3) | 0.042 (2) | 0.018 (2) | 0.019 (2) | 0.008 (2) |
C6 | 0.040 (2) | 0.045 (2) | 0.042 (2) | 0.0131 (17) | 0.0170 (17) | 0.0022 (17) |
C7 | 0.040 (2) | 0.039 (2) | 0.041 (2) | 0.0060 (17) | 0.0168 (17) | 0.0031 (16) |
C8 | 0.043 (2) | 0.052 (2) | 0.049 (2) | −0.0006 (19) | 0.0220 (19) | 0.0009 (19) |
C9 | 0.062 (3) | 0.040 (2) | 0.063 (3) | −0.012 (2) | 0.021 (2) | −0.003 (2) |
C10 | 0.080 (4) | 0.085 (4) | 0.084 (4) | −0.045 (3) | 0.035 (3) | −0.037 (3) |
C11 | 0.060 (3) | 0.134 (5) | 0.056 (3) | −0.006 (4) | 0.013 (3) | −0.018 (4) |
C12 | 0.057 (3) | 0.049 (2) | 0.057 (3) | 0.0098 (19) | 0.033 (2) | 0.0160 (19) |
C13 | 0.059 (3) | 0.040 (2) | 0.065 (3) | 0.0088 (19) | 0.031 (2) | 0.009 (2) |
C14 | 0.079 (4) | 0.052 (3) | 0.066 (3) | 0.014 (2) | 0.016 (3) | 0.002 (2) |
C15 | 0.074 (4) | 0.051 (3) | 0.111 (5) | 0.021 (3) | 0.015 (4) | 0.008 (3) |
C16 | 0.099 (5) | 0.077 (4) | 0.125 (6) | 0.045 (3) | 0.059 (4) | 0.012 (4) |
Geometric parameters (Å, º) top Cd1—N1i | 2.252 (3) | C4—H4A | 0.9300 |
Cd1—N1 | 2.252 (3) | C5—C6 | 1.389 (5) |
Cd1—Cl1i | 2.4513 (12) | C5—H5A | 0.9300 |
Cd1—Cl1 | 2.4513 (12) | C7—C8 | 1.447 (5) |
O1—C8 | 1.354 (5) | C8—C9 | 1.334 (5) |
O1—C11 | 1.392 (6) | C9—C10 | 1.414 (7) |
O2—C13 | 1.352 (5) | C9—H9A | 0.9300 |
O2—C16 | 1.372 (6) | C10—C11 | 1.319 (7) |
N1—C7 | 1.330 (5) | C10—H10A | 0.9300 |
N1—C1 | 1.386 (4) | C11—H11A | 0.9300 |
N2—C7 | 1.356 (5) | C12—C13 | 1.484 (5) |
N2—C6 | 1.387 (5) | C12—H12A | 0.9700 |
N2—C12 | 1.469 (5) | C12—H12B | 0.9700 |
C1—C6 | 1.386 (5) | C13—C14 | 1.320 (6) |
C1—C2 | 1.396 (5) | C14—C15 | 1.424 (7) |
C2—C3 | 1.374 (6) | C14—H14A | 0.9300 |
C2—H2A | 0.9300 | C15—C16 | 1.305 (8) |
C3—C4 | 1.390 (6) | C15—H15A | 0.9300 |
C3—H3A | 0.9300 | C16—H16A | 0.9300 |
C4—C5 | 1.378 (6) | | |
| | | |
N1i—Cd1—N1 | 118.17 (15) | N1—C7—C8 | 123.6 (3) |
N1i—Cd1—Cl1i | 106.27 (8) | N2—C7—C8 | 124.0 (3) |
N1—Cd1—Cl1i | 109.08 (8) | C9—C8—O1 | 111.2 (4) |
N1i—Cd1—Cl1 | 109.08 (8) | C9—C8—C7 | 132.2 (4) |
N1—Cd1—Cl1 | 106.27 (8) | O1—C8—C7 | 116.4 (4) |
Cl1i—Cd1—Cl1 | 107.57 (6) | C8—C9—C10 | 106.3 (4) |
C8—O1—C11 | 105.1 (4) | C8—C9—H9A | 126.8 |
C13—O2—C16 | 105.9 (4) | C10—C9—H9A | 126.8 |
C7—N1—C1 | 105.5 (3) | C11—C10—C9 | 107.3 (4) |
C7—N1—Cd1 | 130.1 (2) | C11—C10—H10A | 126.4 |
C1—N1—Cd1 | 124.4 (2) | C9—C10—H10A | 126.4 |
C7—N2—C6 | 106.5 (3) | C10—C11—O1 | 110.1 (5) |
C7—N2—C12 | 129.4 (3) | C10—C11—H11A | 125.0 |
C6—N2—C12 | 124.1 (3) | O1—C11—H11A | 125.0 |
N1—C1—C6 | 109.2 (3) | N2—C12—C13 | 112.1 (3) |
N1—C1—C2 | 130.6 (4) | N2—C12—H12A | 109.2 |
C6—C1—C2 | 120.2 (4) | C13—C12—H12A | 109.2 |
C3—C2—C1 | 117.3 (4) | N2—C12—H12B | 109.2 |
C3—C2—H2A | 121.4 | C13—C12—H12B | 109.2 |
C1—C2—H2A | 121.4 | H12A—C12—H12B | 107.9 |
C2—C3—C4 | 121.8 (4) | C14—C13—O2 | 110.3 (4) |
C2—C3—H3A | 119.1 | C14—C13—C12 | 133.0 (5) |
C4—C3—H3A | 119.1 | O2—C13—C12 | 116.7 (4) |
C3—C4—C5 | 121.8 (4) | C13—C14—C15 | 106.7 (5) |
C3—C4—H4A | 119.1 | C13—C14—H14A | 126.7 |
C5—C4—H4A | 119.1 | C15—C14—H14A | 126.7 |
C4—C5—C6 | 116.2 (4) | C16—C15—C14 | 106.5 (5) |
C4—C5—H5A | 121.9 | C16—C15—H15A | 126.7 |
C6—C5—H5A | 121.9 | C14—C15—H15A | 126.7 |
N2—C6—C1 | 106.3 (3) | C15—C16—O2 | 110.5 (5) |
N2—C6—C5 | 130.9 (4) | C15—C16—H16A | 124.7 |
C1—C6—C5 | 122.7 (4) | O2—C16—H16A | 124.7 |
N1—C7—N2 | 112.4 (3) | | |
| | | |
N1i—Cd1—N1—C7 | 31.3 (3) | Cd1—N1—C7—C8 | −0.1 (5) |
Cl1i—Cd1—N1—C7 | 152.8 (3) | C6—N2—C7—N1 | 1.3 (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—C8 | 1.3 (6) |
Cl1—Cd1—N1—C1 | 90.0 (3) | C11—O1—C8—C9 | −0.9 (5) |
C7—N1—C1—C6 | 0.8 (4) | C11—O1—C8—C7 | −176.4 (4) |
Cd1—N1—C1—C6 | 179.6 (2) | N1—C7—C8—C9 | −147.9 (5) |
C7—N1—C1—C2 | −179.6 (4) | N2—C7—C8—C9 | 32.1 (7) |
Cd1—N1—C1—C2 | −0.8 (5) | N1—C7—C8—O1 | 26.4 (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—C10 | 1.3 (5) |
C1—C2—C3—C4 | 0.4 (6) | C7—C8—C9—C10 | 175.8 (5) |
C2—C3—C4—C5 | −0.3 (7) | C8—C9—C10—C11 | −1.2 (6) |
C3—C4—C5—C6 | 0.0 (6) | C9—C10—C11—O1 | 0.6 (7) |
C7—N2—C6—C1 | −0.7 (4) | C8—O1—C11—C10 | 0.1 (6) |
C12—N2—C6—C1 | 179.4 (3) | C7—N2—C12—C13 | −103.6 (5) |
C7—N2—C6—C5 | 179.8 (4) | C6—N2—C12—C13 | 76.2 (5) |
C12—N2—C6—C5 | −0.1 (6) | C16—O2—C13—C14 | 1.3 (6) |
N1—C1—C6—N2 | 0.0 (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—C5 | 179.5 (3) | N2—C12—C13—O2 | 66.1 (5) |
C2—C1—C6—C5 | −0.1 (6) | O2—C13—C14—C15 | −0.9 (6) |
C4—C5—C6—N2 | 179.6 (4) | C12—C13—C14—C15 | 177.6 (5) |
C4—C5—C6—C1 | 0.2 (6) | C13—C14—C15—C16 | 0.2 (7) |
C1—N1—C7—N2 | −1.3 (4) | C14—C15—C16—O2 | 0.6 (7) |
Cd1—N1—C7—N2 | 180.0 (2) | C13—O2—C16—C15 | −1.2 (7) |
C1—N1—C7—C8 | 178.6 (4) | | |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···Cl1ii | 0.93 | 2.82 | 3.694 (5) | 156 |
C9—H9A···O2 | 0.93 | 2.49 | 3.256 (6) | 140 |
Symmetry code: (ii) −x+1, −y, −z. |
Experimental details
Crystal data |
Chemical formula | [CdCl2(C16H12N2O2)2] |
Mr | 711.85 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 18.397 (4), 10.451 (2), 17.470 (3) |
β (°) | 116.72 (3) |
V (Å3) | 3000.2 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.95 |
Crystal size (mm) | 0.21 × 0.19 × 0.16 |
|
Data collection |
Diffractometer | Rigaku Saturn diffractometer |
Absorption correction | Multi-scan (REQAB; Jacobson, 1998) |
Tmin, Tmax | 0.825, 0.863 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10628, 2953, 2565 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.110, 1.10 |
No. of reflections | 2953 |
No. of parameters | 195 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.47 |
Selected geometric parameters (Å, º) topCd1—N1 | 2.252 (3) | Cd1—Cl1 | 2.4513 (12) |
| | | |
N1i—Cd1—N1 | 118.17 (15) | N1—Cd1—Cl1 | 106.27 (8) |
N1i—Cd1—Cl1 | 109.08 (8) | Cl1i—Cd1—Cl1 | 107.57 (6) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···Cl1ii | 0.93 | 2.82 | 3.694 (5) | 156.3 |
C9—H9A···O2 | 0.93 | 2.49 | 3.256 (6) | 139.5 |
Symmetry code: (ii) −x+1, −y, −z. |
Acknowledgements
The study was supported by the Science and Technology Department of Henan Province (082102330003).
References
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Yang, H.-X., Zhang, J., Ding, Y.-N. & Meng, X.-R. (2010). Acta Cryst. E66, m578. Web of Science CSD CrossRef IUCr Journals Google Scholar
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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.