Literature DB >> 22590118

(2,2'-Biquinoline-κ(2)N,N')dibromidopalladium(II).

Kwang Ha1.   

Abstract

The Pd(II) ion in the title complex, [PdBr(2)(C(18)H(12)N(2))], is four-coordinated in a distorted square-planar environment by the two N atoms from the chelating 2,2'-biquinoline (Biqu) ligand and two mutually cis Br(-) anions. The Biqu ligand is not planar, the dihedral angle between the quinoline systems being 17.2 (2)°. In the crystal, the complex mol-ecules are connected by C-H⋯Br hydrogen bonds, forming chains along the c axis. When viewed down the b axis, successive chains are stacked in opposite directions. Intra-molecular C-H⋯Br hydrogen bonds are also observed.

Entities:  

Year:  2012        PMID： 22590118      PMCID： PMC3344352          DOI： 10.1107/S1600536812015425

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


Related literature

For the crystal structure of the related chlorido PdII complex [PdCl2(Biqu)], see: Muranishi et al. (2005 ▶).

Experimental

Crystal data

[PdBr2(C18H12N2)] M = 522.50 Triclinic, a = 8.9390 (5) Å b = 9.2187 (5) Å c = 11.1486 (6) Å α = 72.398 (1)° β = 69.318 (1)° γ = 87.258 (1)° V = 817.47 (8) Å3 Z = 2 Mo Kα radiation μ = 6.02 mm−1 T = 200 K 0.17 × 0.12 × 0.11 mm

Data collection

Bruker SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.813, T max = 1.000 5100 measured reflections 3126 independent reflections 2612 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.070 S = 1.12 3126 reflections 208 parameters H-atom parameters constrained Δρmax = 0.67 e Å−3 Δρmin = −0.65 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015425/rk2351sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015425/rk2351Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[PdBr2(C18H12N2)]Z = 2
Mr = 522.50F(000) = 500
Triclinic, P1Dx = 2.123 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9390 (5) ÅCell parameters from 3201 reflections
b = 9.2187 (5) Åθ = 2.6–26.0°
c = 11.1486 (6) ŵ = 6.02 mm−1
α = 72.398 (1)°T = 200 K
β = 69.318 (1)°Block, red
γ = 87.258 (1)°0.17 × 0.12 × 0.11 mm
V = 817.47 (8) Å3
Bruker SMART 1000 CCD diffractometer3126 independent reflections
Radiation source: fine-focus sealed tube2612 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −10→11
Tmin = 0.813, Tmax = 1.000k = −11→10
5100 measured reflectionsl = −13→13
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-atom parameters constrained
S = 1.12w = 1/[σ2(Fo2) + (0.0152P)2 + 2.2618P] where P = (Fo2 + 2Fc2)/3
3126 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.67 e Å−3
0 restraintsΔρmin = −0.65 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.
xyzUiso*/Ueq
Pd10.18588 (4)0.23543 (4)0.12682 (3)0.02511 (10)
Br10.27983 (6)0.30923 (6)0.27917 (5)0.03917 (15)
Br20.46432 (6)0.24992 (6)−0.01469 (5)0.03636 (14)
N1−0.0535 (4)0.2651 (4)0.2177 (4)0.0272 (8)
N20.0935 (4)0.2114 (4)−0.0130 (4)0.0262 (8)
C1−0.1396 (6)0.2604 (5)0.3488 (5)0.0298 (11)
C2−0.0886 (6)0.1742 (6)0.4531 (5)0.0355 (11)
H20.00830.12390.43330.043*
C3−0.1800 (7)0.1634 (6)0.5841 (5)0.0429 (13)
H3−0.14710.10230.65460.051*
C4−0.3222 (7)0.2412 (7)0.6164 (6)0.0492 (15)
H4−0.38210.23550.70730.059*
C5−0.3710 (7)0.3236 (7)0.5160 (6)0.0488 (15)
H5−0.46610.37620.53750.059*
C6−0.2853 (6)0.3342 (6)0.3796 (5)0.0340 (11)
C7−0.3393 (6)0.4086 (6)0.2740 (6)0.0428 (13)
H7−0.43150.46590.29090.051*
C8−0.2613 (6)0.3996 (5)0.1484 (6)0.0350 (12)
H8−0.30320.44270.07890.042*
C9−0.1173 (6)0.3254 (5)0.1219 (5)0.0297 (11)
C10−0.0315 (5)0.2984 (5)−0.0078 (5)0.0267 (10)
C11−0.0841 (6)0.3520 (5)−0.1181 (5)0.0358 (12)
H11−0.17390.4125−0.11250.043*
C12−0.0034 (6)0.3152 (6)−0.2328 (5)0.0386 (13)
H12−0.03030.3588−0.31080.046*
C130.1192 (6)0.2134 (6)−0.2371 (5)0.0367 (12)
C140.1985 (7)0.1614 (7)−0.3494 (5)0.0426 (14)
H140.17460.2013−0.42920.051*
C150.3082 (7)0.0553 (6)−0.3442 (6)0.0432 (13)
H150.35970.0206−0.42000.052*
C160.3463 (6)−0.0038 (6)−0.2269 (5)0.0390 (12)
H160.4214−0.0800−0.22350.047*
C170.2771 (6)0.0469 (5)−0.1187 (5)0.0327 (11)
H170.30490.0066−0.04080.039*
C180.1640 (6)0.1591 (5)−0.1213 (5)0.0293 (10)
U11U22U33U12U13U23
Pd10.02232 (19)0.03082 (19)0.02356 (19)0.00450 (14)−0.01142 (15)−0.00677 (15)
Br10.0325 (3)0.0603 (3)0.0312 (3)0.0010 (2)−0.0168 (2)−0.0163 (3)
Br20.0241 (3)0.0522 (3)0.0343 (3)0.0056 (2)−0.0098 (2)−0.0166 (2)
N10.021 (2)0.030 (2)0.031 (2)0.0009 (16)−0.0103 (17)−0.0085 (17)
N20.023 (2)0.031 (2)0.023 (2)0.0006 (16)−0.0107 (16)−0.0026 (17)
C10.024 (2)0.031 (2)0.037 (3)−0.003 (2)−0.011 (2)−0.012 (2)
C20.034 (3)0.040 (3)0.031 (3)−0.001 (2)−0.011 (2)−0.008 (2)
C30.041 (3)0.049 (3)0.032 (3)−0.009 (3)−0.007 (2)−0.008 (3)
C40.042 (3)0.061 (4)0.035 (3)−0.009 (3)0.006 (3)−0.021 (3)
C50.028 (3)0.053 (3)0.062 (4)−0.002 (3)0.000 (3)−0.032 (3)
C60.021 (2)0.035 (3)0.043 (3)−0.002 (2)−0.006 (2)−0.015 (2)
C70.029 (3)0.038 (3)0.067 (4)0.010 (2)−0.017 (3)−0.026 (3)
C80.028 (3)0.032 (3)0.050 (3)0.004 (2)−0.021 (2)−0.012 (2)
C90.028 (3)0.026 (2)0.041 (3)0.002 (2)−0.020 (2)−0.010 (2)
C100.026 (2)0.023 (2)0.033 (3)−0.0025 (19)−0.015 (2)−0.005 (2)
C110.033 (3)0.034 (3)0.048 (3)0.001 (2)−0.027 (3)−0.008 (2)
C120.046 (3)0.042 (3)0.032 (3)−0.008 (3)−0.026 (3)−0.001 (2)
C130.037 (3)0.043 (3)0.030 (3)−0.006 (2)−0.015 (2)−0.007 (2)
C140.046 (3)0.058 (4)0.023 (3)−0.018 (3)−0.013 (2)−0.007 (2)
C150.040 (3)0.053 (3)0.037 (3)−0.007 (3)−0.004 (3)−0.025 (3)
C160.035 (3)0.038 (3)0.045 (3)−0.005 (2)−0.009 (2)−0.018 (3)
C170.033 (3)0.035 (3)0.030 (3)0.000 (2)−0.010 (2)−0.011 (2)
C180.031 (3)0.033 (3)0.027 (3)−0.005 (2)−0.013 (2)−0.009 (2)
Pd1—N12.064 (4)C7—H70.9500
Pd1—N22.073 (4)C8—C91.407 (7)
Pd1—Br12.4113 (6)C8—H80.9500
Pd1—Br22.4151 (6)C9—C101.468 (7)
N1—C91.349 (6)C10—C111.413 (6)
N1—C11.378 (6)C11—C121.363 (7)
N2—C101.339 (6)C11—H110.9500
N2—C181.369 (6)C12—C131.405 (7)
C1—C21.405 (7)C12—H120.9500
C1—C61.421 (7)C13—C141.415 (7)
C2—C31.373 (7)C13—C181.425 (6)
C2—H20.9500C14—C151.355 (8)
C3—C41.416 (8)C14—H140.9500
C3—H30.9500C15—C161.411 (8)
C4—C51.350 (8)C15—H150.9500
C4—H40.9500C16—C171.357 (7)
C5—C61.415 (7)C16—H160.9500
C5—H50.9500C17—C181.413 (7)
C6—C71.404 (7)C17—H170.9500
C7—C81.352 (7)
N1—Pd1—N278.90 (15)C7—C8—C9119.2 (5)
N1—Pd1—Br196.71 (11)C7—C8—H8120.4
N2—Pd1—Br1169.85 (10)C9—C8—H8120.4
N1—Pd1—Br2167.99 (11)N1—C9—C8121.8 (5)
N2—Pd1—Br296.02 (11)N1—C9—C10114.9 (4)
Br1—Pd1—Br286.49 (2)C8—C9—C10123.1 (4)
C9—N1—C1119.3 (4)N2—C10—C11121.6 (4)
C9—N1—Pd1109.1 (3)N2—C10—C9116.2 (4)
C1—N1—Pd1130.2 (3)C11—C10—C9122.1 (4)
C10—N2—C18120.3 (4)C12—C11—C10118.7 (5)
C10—N2—Pd1107.9 (3)C12—C11—H11120.7
C18—N2—Pd1129.2 (3)C10—C11—H11120.7
N1—C1—C2119.9 (4)C11—C12—C13120.8 (5)
N1—C1—C6120.1 (4)C11—C12—H12119.6
C2—C1—C6119.9 (5)C13—C12—H12119.6
C3—C2—C1119.4 (5)C12—C13—C14123.4 (5)
C3—C2—H2120.3C12—C13—C18117.9 (5)
C1—C2—H2120.3C14—C13—C18118.7 (5)
C2—C3—C4121.6 (5)C15—C14—C13120.7 (5)
C2—C3—H3119.2C15—C14—H14119.6
C4—C3—H3119.2C13—C14—H14119.6
C5—C4—C3118.8 (5)C14—C15—C16120.3 (5)
C5—C4—H4120.6C14—C15—H15119.9
C3—C4—H4120.6C16—C15—H15119.9
C4—C5—C6122.2 (5)C17—C16—C15120.9 (5)
C4—C5—H5118.9C17—C16—H16119.6
C6—C5—H5118.9C15—C16—H16119.6
C7—C6—C5123.6 (5)C16—C17—C18120.4 (5)
C7—C6—C1118.3 (5)C16—C17—H17119.8
C5—C6—C1118.0 (5)C18—C17—H17119.8
C8—C7—C6120.6 (5)N2—C18—C17121.0 (4)
C8—C7—H7119.7N2—C18—C13120.1 (4)
C6—C7—H7119.7C17—C18—C13118.9 (4)
N2—Pd1—N1—C9−29.4 (3)C1—N1—C9—C10−168.6 (4)
Br1—Pd1—N1—C9141.3 (3)Pd1—N1—C9—C1023.2 (5)
Br2—Pd1—N1—C936.4 (7)C7—C8—C9—N1−1.0 (7)
N2—Pd1—N1—C1164.1 (4)C7—C8—C9—C10174.6 (5)
Br1—Pd1—N1—C1−25.1 (4)C18—N2—C10—C11−6.7 (7)
Br2—Pd1—N1—C1−130.0 (5)Pd1—N2—C10—C11156.5 (4)
N1—Pd1—N2—C1030.8 (3)C18—N2—C10—C9169.1 (4)
Br1—Pd1—N2—C10−34.3 (8)Pd1—N2—C10—C9−27.7 (4)
Br2—Pd1—N2—C10−138.2 (3)N1—C9—C10—N23.3 (6)
N1—Pd1—N2—C18−168.0 (4)C8—C9—C10—N2−172.6 (4)
Br1—Pd1—N2—C18126.9 (5)N1—C9—C10—C11179.1 (4)
Br2—Pd1—N2—C1823.0 (4)C8—C9—C10—C113.1 (7)
C9—N1—C1—C2168.6 (4)N2—C10—C11—C12−0.9 (7)
Pd1—N1—C1—C2−26.1 (6)C9—C10—C11—C12−176.4 (4)
C9—N1—C1—C6−7.3 (6)C10—C11—C12—C136.4 (7)
Pd1—N1—C1—C6158.0 (3)C11—C12—C13—C14174.8 (5)
N1—C1—C2—C3−176.4 (4)C11—C12—C13—C18−4.5 (7)
C6—C1—C2—C3−0.5 (7)C12—C13—C14—C15−175.5 (5)
C1—C2—C3—C4−2.1 (8)C18—C13—C14—C153.8 (8)
C2—C3—C4—C52.2 (8)C13—C14—C15—C16−0.7 (8)
C3—C4—C5—C60.3 (9)C14—C15—C16—C17−1.6 (8)
C4—C5—C6—C7174.7 (5)C15—C16—C17—C180.6 (7)
C4—C5—C6—C1−2.8 (8)C10—N2—C18—C17−169.1 (4)
N1—C1—C6—C71.1 (7)Pd1—N2—C18—C1731.7 (6)
C2—C1—C6—C7−174.7 (4)C10—N2—C18—C138.5 (6)
N1—C1—C6—C5178.7 (4)Pd1—N2—C18—C13−150.7 (4)
C2—C1—C6—C52.9 (7)C16—C17—C18—N2−179.9 (4)
C5—C6—C7—C8−172.2 (5)C16—C17—C18—C132.5 (7)
C1—C6—C7—C85.3 (7)C12—C13—C18—N2−3.0 (7)
C6—C7—C8—C9−5.3 (8)C14—C13—C18—N2177.7 (4)
C1—N1—C9—C87.4 (7)C12—C13—C18—C17174.7 (4)
Pd1—N1—C9—C8−160.8 (4)C14—C13—C18—C17−4.7 (7)
D—H···AD—HH···AD···AD—H···A
C2—H2···Br10.952.733.252 (5)116
C14—H14···Br1i0.952.903.754 (5)150
C17—H17···Br20.952.853.261 (5)107
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2⋯Br10.952.733.252 (5)116
C14—H14⋯Br1i0.952.903.754 (5)150
C17—H17⋯Br20.952.853.261 (5)107

Symmetry code: (i) .

  3 in total

1.  (2,2'-Biquinoline-kappa(2)N,N')dichloropalladium(II), -copper(II) and -zinc(II).

Authors:  Yasunori Muranishi; Yue Wang; Mamiko Odoko; Nobuo Okabe
Journal:  Acta Crystallogr C       Date:  2005-05-20       Impact factor: 1.172

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  3 in total

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