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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1349.
Published online 2008 September 30. doi:  10.1107/S1600536808030845
PMCID: PMC2959319

Dibromidobis[2-(dicyclo­hexyl­phosphan­yl)­biphenyl-κP]palladium(II)

Abstract

The title compound, [PdBr2(C24H31P)2], has a distorted trans square-planar coordination of the Pd atom, which occupies an inversion centre. The most important bond distances include Pd—P of 2.380 (2) Å and Pd—Br of 2.515 (2) Å. Weak inter­molecular π–π inter­actions between the benzene rings of adjacent mol­ecules [centroid–centroid distance = 3.949 (6) Å] are present via crystallographic inversion centres, resulting in a one-dimensional supra­molecular architecture.

Related literature

For related literature, see: Barder et al. (2005 [triangle]); Christmann et al. (2006 [triangle]); Stark & Whitmire (1997 [triangle]); Tomori et al. (2000 [triangle]); Tsuji (1995 [triangle]); Xu et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1349-scheme1.jpg

Experimental

Crystal data

  • [PdBr2(C24H31P)2]
  • M r = 967.14
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1349-efi1.jpg
  • a = 9.817 (8) Å
  • b = 9.827 (8) Å
  • c = 11.957 (10) Å
  • α = 91.582 (11)°
  • β = 108.822 (10)°
  • γ = 103.713 (10)°
  • V = 1053.9 (15) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 2.44 mm−1
  • T = 291 (2) K
  • 0.14 × 0.10 × 0.09 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.723, T max = 0.803
  • 7316 measured reflections
  • 3811 independent reflections
  • 2810 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.180
  • S = 1.10
  • 3811 reflections
  • 241 parameters
  • H-atom parameters constrained
  • Δρmax = 0.71 e Å−3
  • Δρmin = −1.42 e Å−3

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]) and SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030845/si2114sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030845/si2114Isup2.hkl

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

Acknowledgments

This work was supported by the Doctoral Foundation of Luoyang Normal University, People’s Republic of China.

supplementary crystallographic information

Comment

Phosphine complexes of palladium have widely been used as catalysts for various reactions (Tsuji, 1995). These complexes are easily prepared from palladium(II) salts and an excess of phosphine ligands. Among them, monophosphinobiaryl complexes of palladium are one of the most important ones (Barder et al., 2005; Christmann et al., 2006; Xu et al., 2007).

The title complex has crystallographic inversion symmetry Ci (Fig.1). The Pd atom is in a square-planar environment, while the trans 2-(Dicyclohexylphosphanyl)biphenyl ligands are in an eclipsed conformation. The dihedral angles of the benzene rings are 60.8 (2)°. The Pd—P [2.380 (2) Å] and Pd—Br [2.515 (5) Å] bond lengths are longer than the related triphenylphosphine complex of palladium [2.336 (2)Å and 2.4169 (13) Å](Stark & Whitmire, 1997) possibly due to the steric bulk of the ligand. Weak intermolecular π···π interactions between the benzene rings C19 - C24 (Cg4) of inversion related adjacent molecules [centroid-centroid distance Cg4···Cg4ii is 3.949 (6) Å, the perpendicular distance Cg4 on ring Cg4ii is 3.582 Å, and the slippage is 1.663 Å, symmetry code ii = 1 - x, 1 - y, 1 - z] were calculated for the structure of the title complex with the programme PLATON (Spek, 2003), resulting in a one-dimensional supramolecular architecture.

Experimental

2-(Dicyclohexylphosphanyl)biphenyl was prepared as described in the literature (Tomori et al., 2000). A solution of PdBr2(PhCN)2 (1 mmol) and 2-(Dicyclohexylphosphanyl)biphenyl (2 mmol) in dry benzene (5 ml) was stirred for 1 day, removal of solvent resulted in a yellow powder that was recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired product as yellow crystals suitable for single-crystal X-ray diffraction.

Refinement

H atoms were placed in calculated positions (Csp2—H = 0.93 Å, Csp3—H = 0.97 -0.98 Å) and refined as riding on their carriers with isotropic displacement parameters Uiso(H) = 1.2 times Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound with displacement ellipsoids of the non-hydrogen atoms drawn at the 30% probability level. Inversion related atoms are labelled with an A.(Symmetry code: 2 - x, 1 - y, 1 - z).
Fig. 2.
Partial view of the crystal packing showing the formation of the chain motif of molecules formed by the intermolecular π···π interactions, extending along the a axis.

Crystal data

[PdBr2(C24H31P)2]Z = 1
Mr = 967.14F(000) = 496
Triclinic, P1Dx = 1.524 Mg m3
a = 9.817 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.827 (8) ÅCell parameters from 1503 reflections
c = 11.957 (10) Åθ = 2.4–21.7°
α = 91.582 (11)°µ = 2.45 mm1
β = 108.822 (10)°T = 291 K
γ = 103.713 (10)°Block, yellow
V = 1053.9 (15) Å30.14 × 0.10 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer3811 independent reflections
Radiation source: fine-focus sealed tube2810 reflections with I > 2σ(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.723, Tmax = 0.803k = −11→11
7316 measured reflectionsl = −14→14

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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0609P)2 + 7.3363P] where P = (Fo2 + 2Fc2)/3
3811 reflections(Δ/σ)max < 0.001
241 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = −1.42 e Å3

Special details

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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)

xyzUiso*/Ueq
Pd11.00000.50000.50000.0252 (2)
Br10.96825 (13)0.71510 (13)0.59715 (10)0.0612 (4)
P10.8353 (2)0.5540 (2)0.32229 (17)0.0267 (5)
C10.7959 (9)0.4354 (9)0.1852 (7)0.0306 (18)
H10.77030.33920.20600.037*
C20.6642 (9)0.4454 (10)0.0766 (7)0.038 (2)
H2A0.57630.43780.09900.045*
H2B0.68700.53580.04680.045*
C30.6343 (10)0.3264 (10)−0.0199 (8)0.044 (2)
H3A0.60210.23660.00780.053*
H3B0.55460.3355−0.09030.053*
C40.7702 (10)0.3287 (10)−0.0518 (8)0.045 (2)
H4A0.79450.4131−0.08930.054*
H4B0.74880.2479−0.10900.054*
C50.9032 (10)0.3258 (9)0.0551 (8)0.038 (2)
H5A0.99030.33440.03150.046*
H5B0.88430.23690.08790.046*
C60.9318 (9)0.4476 (9)0.1490 (7)0.0362 (19)
H6A1.01670.44560.21800.043*
H6B0.95460.53660.11710.043*
C70.9148 (9)0.7385 (9)0.2981 (7)0.0330 (18)
H70.90690.79810.36160.040*
C80.8334 (10)0.7900 (9)0.1839 (8)0.044 (2)
H8A0.84070.73750.11710.052*
H8B0.72880.77240.17510.052*
C90.8963 (11)0.9454 (10)0.1819 (10)0.056 (3)
H9A0.84710.97230.10480.067*
H9B0.87610.99870.24150.067*
C101.0617 (11)0.9819 (11)0.2059 (10)0.057 (3)
H10A1.08080.94100.13960.068*
H10B1.09931.08350.21240.068*
C111.1426 (10)0.9292 (10)0.3177 (10)0.054 (3)
H11A1.13450.97940.38530.064*
H11B1.24740.94820.32680.064*
C121.0801 (9)0.7721 (9)0.3166 (8)0.039 (2)
H12A1.13220.74190.39140.047*
H12B1.09570.72100.25310.047*
C130.6373 (9)0.2210 (10)0.3590 (8)0.043 (2)
H130.70630.27130.42960.052*
C140.6340 (11)0.0838 (10)0.3309 (9)0.048 (2)
H140.70070.04220.38320.058*
C150.5362 (12)0.0082 (11)0.2291 (10)0.055 (3)
H150.5373−0.08410.21070.066*
C160.4362 (12)0.0670 (11)0.1533 (9)0.056 (3)
H160.36890.01480.08290.067*
C170.4337 (10)0.2035 (10)0.1801 (8)0.047 (2)
H170.36180.24120.12920.056*
C180.5374 (9)0.2858 (9)0.2823 (7)0.0338 (19)
C190.5333 (9)0.4319 (9)0.3139 (7)0.0324 (18)
C200.4018 (9)0.4472 (10)0.3274 (8)0.043 (2)
H200.32190.36780.31140.051*
C210.3852 (10)0.5738 (11)0.3630 (8)0.047 (2)
H210.29670.57950.37330.056*
C220.4983 (11)0.6902 (11)0.3831 (8)0.046 (2)
H220.48710.77700.40560.056*
C230.6325 (10)0.6814 (10)0.3703 (8)0.040 (2)
H230.71040.76260.38620.048*
C240.6521 (9)0.5536 (9)0.3340 (7)0.0306 (18)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pd10.0260 (5)0.0262 (5)0.0248 (5)0.0099 (4)0.0083 (3)0.0043 (3)
Br10.0626 (7)0.0682 (8)0.0511 (7)0.0210 (6)0.0141 (5)0.0072 (5)
P10.0255 (10)0.0281 (11)0.0275 (10)0.0093 (8)0.0084 (8)0.0049 (8)
C10.032 (4)0.035 (5)0.031 (4)0.014 (4)0.014 (3)0.007 (3)
C20.032 (4)0.046 (5)0.036 (5)0.015 (4)0.007 (4)0.004 (4)
C30.043 (5)0.054 (6)0.029 (5)0.009 (4)0.007 (4)0.000 (4)
C40.051 (6)0.045 (6)0.036 (5)−0.001 (4)0.021 (4)−0.005 (4)
C50.047 (5)0.036 (5)0.043 (5)0.015 (4)0.028 (4)0.004 (4)
C60.038 (5)0.038 (5)0.034 (4)0.012 (4)0.013 (4)0.005 (4)
C70.032 (4)0.035 (5)0.036 (5)0.014 (4)0.012 (4)0.007 (4)
C80.040 (5)0.034 (5)0.056 (6)0.010 (4)0.013 (4)0.020 (4)
C90.047 (6)0.039 (6)0.077 (7)0.012 (5)0.013 (5)0.024 (5)
C100.056 (6)0.041 (6)0.072 (7)0.007 (5)0.023 (6)0.019 (5)
C110.033 (5)0.050 (6)0.073 (7)0.002 (4)0.019 (5)0.013 (5)
C120.031 (4)0.037 (5)0.051 (5)0.010 (4)0.015 (4)0.014 (4)
C130.031 (5)0.059 (6)0.039 (5)0.016 (4)0.008 (4)0.010 (4)
C140.052 (6)0.037 (6)0.059 (6)0.020 (5)0.017 (5)0.013 (5)
C150.059 (6)0.032 (6)0.068 (7)0.005 (5)0.021 (6)−0.002 (5)
C160.055 (6)0.046 (6)0.052 (6)−0.005 (5)0.011 (5)−0.004 (5)
C170.037 (5)0.045 (6)0.044 (5)0.001 (4)0.002 (4)0.007 (4)
C180.030 (4)0.031 (5)0.039 (5)0.003 (3)0.015 (4)0.003 (4)
C190.029 (4)0.034 (5)0.035 (4)0.010 (3)0.011 (3)0.004 (4)
C200.027 (4)0.048 (6)0.052 (6)0.010 (4)0.012 (4)0.007 (4)
C210.030 (5)0.067 (7)0.053 (6)0.023 (5)0.018 (4)0.009 (5)
C220.055 (6)0.051 (6)0.051 (6)0.034 (5)0.026 (5)0.012 (5)
C230.038 (5)0.040 (5)0.047 (5)0.015 (4)0.019 (4)0.005 (4)
C240.033 (4)0.034 (5)0.029 (4)0.014 (4)0.012 (3)0.006 (3)

Geometric parameters (Å, °)

Pd1—P1i2.380 (2)C9—H9B0.9700
Pd1—P12.380 (2)C10—C111.495 (14)
Pd1—Br1i2.515 (2)C10—H10A0.9700
Pd1—Br12.515 (2)C10—H10B0.9700
P1—C241.848 (8)C11—C121.518 (13)
P1—C11.862 (8)C11—H11A0.9700
P1—C71.866 (8)C11—H11B0.9700
C1—C61.510 (11)C12—H12A0.9700
C1—C21.533 (11)C12—H12B0.9700
C1—H10.9800C13—C141.371 (13)
C2—C31.527 (12)C13—C181.398 (12)
C2—H2A0.9700C13—H130.9300
C2—H2B0.9700C14—C151.347 (14)
C3—C41.496 (12)C14—H140.9300
C3—H3A0.9700C15—C161.358 (14)
C3—H3B0.9700C15—H150.9300
C4—C51.511 (12)C16—C171.378 (14)
C4—H4A0.9700C16—H160.9300
C4—H4B0.9700C17—C181.391 (12)
C5—C61.527 (11)C17—H170.9300
C5—H5A0.9700C18—C191.488 (12)
C5—H5B0.9700C19—C201.393 (11)
C6—H6A0.9700C19—C241.410 (11)
C6—H6B0.9700C20—C211.367 (13)
C7—C81.512 (11)C20—H200.9300
C7—C121.518 (11)C21—C221.345 (14)
C7—H70.9800C21—H210.9300
C8—C91.509 (12)C22—C231.396 (12)
C8—H8A0.9700C22—H220.9300
C8—H8B0.9700C23—C241.394 (12)
C9—C101.505 (14)C23—H230.9300
C9—H9A0.9700
P1i—Pd1—P1180.0C10—C9—C8111.9 (8)
P1i—Pd1—Br1i85.15 (7)C10—C9—H9A109.2
P1—Pd1—Br1i94.85 (7)C8—C9—H9A109.2
P1i—Pd1—Br194.85 (7)C10—C9—H9B109.2
P1—Pd1—Br185.15 (7)C8—C9—H9B109.2
Br1i—Pd1—Br1180.000 (2)H9A—C9—H9B107.9
C24—P1—C1106.1 (4)C11—C10—C9111.8 (8)
C24—P1—C7104.9 (4)C11—C10—H10A109.2
C1—P1—C7108.6 (4)C9—C10—H10A109.2
C24—P1—Pd1112.3 (3)C11—C10—H10B109.2
C1—P1—Pd1115.8 (3)C9—C10—H10B109.2
C7—P1—Pd1108.5 (3)H10A—C10—H10B107.9
C6—C1—C2109.2 (7)C10—C11—C12111.6 (8)
C6—C1—P1112.5 (6)C10—C11—H11A109.3
C2—C1—P1116.7 (5)C12—C11—H11A109.3
C6—C1—H1105.9C10—C11—H11B109.3
C2—C1—H1105.9C12—C11—H11B109.3
P1—C1—H1105.9H11A—C11—H11B108.0
C3—C2—C1109.1 (7)C11—C12—C7110.5 (7)
C3—C2—H2A109.9C11—C12—H12A109.6
C1—C2—H2A109.9C7—C12—H12A109.6
C3—C2—H2B109.9C11—C12—H12B109.6
C1—C2—H2B109.9C7—C12—H12B109.6
H2A—C2—H2B108.3H12A—C12—H12B108.1
C4—C3—C2111.7 (7)C14—C13—C18120.4 (9)
C4—C3—H3A109.3C14—C13—H13119.8
C2—C3—H3A109.3C18—C13—H13119.8
C4—C3—H3B109.3C15—C14—C13121.4 (9)
C2—C3—H3B109.3C15—C14—H14119.3
H3A—C3—H3B107.9C13—C14—H14119.3
C3—C4—C5112.5 (7)C14—C15—C16119.8 (10)
C3—C4—H4A109.1C14—C15—H15120.1
C5—C4—H4A109.1C16—C15—H15120.1
C3—C4—H4B109.1C15—C16—C17120.4 (10)
C5—C4—H4B109.1C15—C16—H16119.8
H4A—C4—H4B107.8C17—C16—H16119.8
C4—C5—C6109.5 (7)C16—C17—C18120.9 (9)
C4—C5—H5A109.8C16—C17—H17119.6
C6—C5—H5A109.8C18—C17—H17119.6
C4—C5—H5B109.8C17—C18—C13117.0 (8)
C6—C5—H5B109.8C17—C18—C19121.4 (8)
H5A—C5—H5B108.2C13—C18—C19121.4 (8)
C1—C6—C5110.0 (7)C20—C19—C24118.2 (8)
C1—C6—H6A109.7C20—C19—C18116.4 (7)
C5—C6—H6A109.7C24—C19—C18125.4 (7)
C1—C6—H6B109.7C21—C20—C19122.8 (9)
C5—C6—H6B109.7C21—C20—H20118.6
H6A—C6—H6B108.2C19—C20—H20118.6
C8—C7—C12109.9 (7)C22—C21—C20119.2 (8)
C8—C7—P1117.0 (6)C22—C21—H21120.4
C12—C7—P1113.5 (5)C20—C21—H21120.4
C8—C7—H7105.1C21—C22—C23120.5 (9)
C12—C7—H7105.1C21—C22—H22119.8
P1—C7—H7105.1C23—C22—H22119.8
C9—C8—C7111.9 (8)C24—C23—C22121.3 (9)
C9—C8—H8A109.2C24—C23—H23119.3
C7—C8—H8A109.2C22—C23—H23119.3
C9—C8—H8B109.2C23—C24—C19117.9 (7)
C7—C8—H8B109.2C23—C24—P1117.6 (6)
H8A—C8—H8B107.9C19—C24—P1124.5 (6)
P1i—Pd1—P1—C24103 (35)C9—C10—C11—C1254.5 (12)
Br1i—Pd1—P1—C24120.1 (3)C10—C11—C12—C7−57.0 (11)
Br1—Pd1—P1—C24−59.9 (3)C8—C7—C12—C1157.1 (10)
P1i—Pd1—P1—C1−20 (33)P1—C7—C12—C11−169.7 (7)
Br1i—Pd1—P1—C1−2.1 (3)C18—C13—C14—C150.5 (15)
Br1—Pd1—P1—C1177.9 (3)C13—C14—C15—C16−1.5 (16)
P1i—Pd1—P1—C7−142 (33)C14—C15—C16—C17−0.2 (16)
Br1i—Pd1—P1—C7−124.4 (3)C15—C16—C17—C182.9 (15)
Br1—Pd1—P1—C755.6 (3)C16—C17—C18—C13−3.7 (14)
C24—P1—C1—C6168.1 (6)C16—C17—C18—C19−178.3 (9)
C7—P1—C1—C655.8 (6)C14—C13—C18—C172.1 (13)
Pd1—P1—C1—C6−66.5 (6)C14—C13—C18—C19176.6 (8)
C24—P1—C1—C240.7 (7)C17—C18—C19—C2057.9 (11)
C7—P1—C1—C2−71.6 (7)C13—C18—C19—C20−116.4 (9)
Pd1—P1—C1—C2166.1 (5)C17—C18—C19—C24−123.8 (9)
C6—C1—C2—C359.6 (9)C13—C18—C19—C2461.9 (12)
P1—C1—C2—C3−171.5 (6)C24—C19—C20—C21−2.3 (13)
C1—C2—C3—C4−55.9 (10)C18—C19—C20—C21176.1 (8)
C2—C3—C4—C554.7 (11)C19—C20—C21—C221.9 (14)
C3—C4—C5—C6−55.3 (10)C20—C21—C22—C23−1.4 (14)
C2—C1—C6—C5−61.9 (9)C21—C22—C23—C241.5 (14)
P1—C1—C6—C5166.9 (6)C22—C23—C24—C19−1.8 (12)
C4—C5—C6—C158.9 (9)C22—C23—C24—P1−179.1 (7)
C24—P1—C7—C8−64.7 (7)C20—C19—C24—C232.2 (12)
C1—P1—C7—C848.4 (7)C18—C19—C24—C23−176.0 (8)
Pd1—P1—C7—C8175.1 (6)C20—C19—C24—P1179.2 (6)
C24—P1—C7—C12165.6 (6)C18—C19—C24—P11.0 (12)
C1—P1—C7—C12−81.3 (7)C1—P1—C24—C23−139.6 (6)
Pd1—P1—C7—C1245.3 (7)C7—P1—C24—C23−24.7 (7)
C12—C7—C8—C9−56.0 (10)Pd1—P1—C24—C2393.0 (6)
P1—C7—C8—C9172.6 (7)C1—P1—C24—C1943.4 (8)
C7—C8—C9—C1054.0 (12)C7—P1—C24—C19158.3 (7)
C8—C9—C10—C11−52.8 (13)Pd1—P1—C24—C19−84.1 (7)

Symmetry codes: (i) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2114).

References

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