metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

{Bis[2-(di­cyclo­hexyl­phosphino)­phen­yl]methyl­silyl-κ3P,Si,P′}chloridopalladium(II)

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
*Correspondence e-mail: liyhnju@hotmail.com

(Received 26 August 2008; accepted 10 September 2008; online 17 September 2008)

In the title compound, [Pd(C37H55P2Si)Cl], the Pd atom has a distorted square-planar geometry. The two five-membered rings adopt envelope conformations, while the four cyclo­hexane rings have chair conformations. The two planar aromatic rings are oriented at a dihedral angle of 28.79 (3)°.

Related literature

For general background, see: Moulton & Shaw (1976[Moulton, C. J. & Shaw, B. L. (1976). J. Chem. Soc. Dalton Trans. pp. 1020-1024.]); Boom & Milstein (2003[Boom, M. E. van der & Milstein, D. (2003). Chem. Rev. 103, 1759-1792.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • [Pd(C37H55P2Si)Cl]

  • Mr = 731.69

  • Monoclinic, P 21 /c

  • a = 13.079 (3) Å

  • b = 16.632 (3) Å

  • c = 17.739 (4) Å

  • β = 108.55 (3)°

  • V = 3658.3 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.72 mm−1

  • T = 153 (2) K

  • 0.49 × 0.4 × 0.4 mm

Data collection
  • Bruker P4 diffractometer

  • Absorption correction: multi-scan (CrystalClear, Rigaku, 2005[Rigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.690, Tmax = 0.758

  • 26471 measured reflections

  • 8379 independent reflections

  • 6612 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.059

  • S = 0.93

  • 8379 reflections

  • 380 parameters

  • H-atom parameters constrained

  • Δρmax = 0.83 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Selected geometric parameters (Å, °)

Pd1—P2 2.3132 (6)
Pd1—Cl1 2.4584 (6)
P1—Pd1 2.3111 (7)
Si1—Pd1 2.2829 (6)
Si1—Pd1—P1 83.42 (3)
Si1—Pd1—P2 83.56 (3)
P1—Pd1—P2 160.56 (4)
Si1—Pd1—Cl1 178.18 (4)
P1—Pd1—Cl1 94.96 (3)
P2—Pd1—Cl1 98.21 (3)

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2005[Rigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Pincer ligands incorporating two phosphine arms and a central donor site have attracted a substantial amount of interest, since the initial investigations of PCP ligands (Moulton & Shaw, 1976). Several variations of the central donor atom have been explored (Boom & Milstein, 2003). However, the "PSiP" pincer-like transition-metal complexes have rarely been reported. The title compound was obtained during our work on the phosphinoalkylsilyl complexes, and we report herein its crystal structure.

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. The Pd atom has a distorted square geometry (Table 1). Rings A (C2–C7) and D (C20–C25) are, of course, planar, and they are oriented at a dihedral angle of 28.79 (3)°. The six-membered rings B (C8–C13), C (C14–C19), E (C26–C31) and F (C32–C37) are not planar, having total puckering amplitudes, QT, of 0.570 (3), 0.580 (3), 0.566 (3) and 0.583 (3) and chair conformations [ϕ = -16.92 (2)°, θ = 2.08 (3)°; ϕ = -100.91 (3)°, θ = 1.43 (3)°; ϕ = -40.78 (2)°, θ = 2.27 (3)° and ϕ = -155.29 (3)°, θ = 176.23 (4)°, respectively] (Cremer & Pople, 1975), while rings G (Pd1/P1/Si1/C2/C7) and H (Pd1/P2/Si1/C20/C25) adopt envelope conformations, with Si1 and Pd1 atoms displaced by -0.422 (3) and 0.694 (2) Å from the planes of the other ring atoms.

Related literature top

For general background, see: Moulton & Shaw (1976); Boom & Milstein (2003). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

Dropwise addition of a solution of MeSiH(Cy2PC6H4)2 (124 mg, 0.21 mmol) in dry THF (5 ml) to a solution of [Pd(COD)Cl2] (43 mg, 0.21 mmol) in a mixture of THF (7 ml) and NEt3 (1 ml) resulted in rapid formation of a colorless precipitate. Removal of the volatiles left solid material, which after through washing left the product (yield; 130 mg, 85%). Crystals suitable for X-ray analysis were obtained by slow evaporation of a benzene (5 ml) solution of the title compound (28 mg) after 1 d.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: CrystalClear, Rigaku, 2005; cell refinement: CrystalClear, Rigaku, 2005; data reduction: CrystalStructure (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
{Bis[2-(dicyclohexylphosphino)phenyl]methylsilyl- κ3P,Si,P'}chloridopalladium(II) top
Crystal data top
[Pd(C37H55P2Si)Cl]F(000) = 1536
Mr = 731.69Dx = 1.328 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8380 reflections
a = 13.079 (3) Åθ = 2.6–27.5°
b = 16.632 (3) ŵ = 0.73 mm1
c = 17.739 (4) ÅT = 153 K
β = 108.55 (3)°Plate, colourless
V = 3658.3 (15) Å30.49 × 0.4 × 0.4 mm
Z = 4
Data collection top
Bruker P4
diffractometer
8379 independent reflections
Radiation source: fine-focus sealed tube6612 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 1.6°
ω scansh = 1616
Absorption correction: multi-scan
(CrystalClear, Rigaku, 2005)
k = 2120
Tmin = 0.690, Tmax = 0.758l = 2223
26471 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0286P)2]
where P = (Fo2 + 2Fc2)/3
8379 reflections(Δ/σ)max = 0.002
380 parametersΔρmax = 0.83 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
[Pd(C37H55P2Si)Cl]V = 3658.3 (15) Å3
Mr = 731.69Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.079 (3) ŵ = 0.73 mm1
b = 16.632 (3) ÅT = 153 K
c = 17.739 (4) Å0.49 × 0.4 × 0.4 mm
β = 108.55 (3)°
Data collection top
Bruker P4
diffractometer
8379 independent reflections
Absorption correction: multi-scan
(CrystalClear, Rigaku, 2005)
6612 reflections with I > 2σ(I)
Tmin = 0.690, Tmax = 0.758Rint = 0.029
26471 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.059H-atom parameters constrained
S = 0.93Δρmax = 0.83 e Å3
8379 reflectionsΔρmin = 0.24 e Å3
380 parameters
Special details top

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 taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used 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) top
xyzUiso*/Ueq
Pd10.776955 (11)0.199184 (8)0.842716 (8)0.01619 (5)
Cl10.74782 (4)0.10723 (3)0.94246 (3)0.02368 (11)
P10.61347 (4)0.26445 (3)0.81739 (3)0.01750 (11)
P20.92123 (4)0.13330 (3)0.82162 (3)0.01924 (11)
Si10.80048 (4)0.28746 (3)0.75107 (3)0.01937 (12)
C10.88282 (17)0.38076 (11)0.79094 (12)0.0281 (5)
H90.95660.36590.81690.042*
H100.85470.40700.82840.042*
H110.87890.41670.74780.042*
C20.66587 (16)0.33238 (11)0.69303 (11)0.0217 (4)
C30.64531 (18)0.37785 (12)0.62354 (12)0.0311 (5)
H10.69680.37980.59760.037*
C40.55014 (19)0.42001 (12)0.59254 (13)0.0355 (5)
H20.53730.44830.54520.043*
C50.47352 (17)0.42045 (11)0.63167 (12)0.0304 (5)
H30.41080.45060.61190.037*
C60.49142 (16)0.37573 (11)0.70008 (11)0.0242 (4)
H40.44030.37580.72640.029*
C70.58586 (15)0.33015 (10)0.73039 (11)0.0197 (4)
C80.58284 (16)0.32556 (11)0.89412 (11)0.0220 (4)
H520.51410.35300.86910.026*
C90.66938 (17)0.38988 (11)0.92582 (12)0.0264 (5)
H120.67350.42360.88230.032*
H130.73900.36430.94900.032*
C100.64322 (19)0.44220 (12)0.98907 (13)0.0353 (5)
H140.70140.48021.01090.042*
H150.57790.47260.96420.042*
C110.62822 (18)0.39211 (12)1.05543 (12)0.0336 (5)
H160.60600.42651.09160.040*
H170.69640.36741.08500.040*
C120.54384 (19)0.32688 (13)1.02360 (13)0.0355 (5)
H180.47390.35170.99970.043*
H190.53970.29341.06730.043*
C130.57070 (18)0.27452 (12)0.96181 (12)0.0287 (5)
H200.63730.24560.98680.034*
H210.51380.23540.94090.034*
C140.50756 (15)0.18646 (10)0.78938 (11)0.0189 (4)
H530.52100.14990.83480.023*
C150.52037 (16)0.13733 (12)0.72025 (12)0.0273 (5)
H220.50900.17200.67430.033*
H230.59330.11650.73460.033*
C160.44090 (18)0.06758 (12)0.69850 (14)0.0363 (5)
H240.44870.03960.65270.044*
H250.45700.02990.74240.044*
C170.32561 (17)0.09697 (12)0.67967 (14)0.0359 (5)
H260.30700.13070.63260.043*
H270.27690.05130.66870.043*
C180.31299 (17)0.14426 (12)0.74885 (14)0.0336 (5)
H280.32640.10940.79480.040*
H290.23970.16420.73550.040*
C190.39173 (16)0.21510 (11)0.76928 (13)0.0289 (5)
H300.37540.25170.72440.035*
H310.38300.24420.81430.035*
C200.87194 (15)0.23153 (11)0.68936 (11)0.0206 (4)
C210.87080 (16)0.25321 (12)0.61293 (12)0.0256 (4)
H50.83120.29780.58840.031*
C220.92774 (18)0.20930 (12)0.57330 (12)0.0306 (5)
H60.92510.22400.52210.037*
C230.98812 (18)0.14409 (13)0.60931 (13)0.0327 (5)
H71.02720.11540.58270.039*
C240.99120 (17)0.12082 (12)0.68487 (12)0.0288 (5)
H81.03240.07680.70910.035*
C250.93198 (15)0.16385 (11)0.72491 (11)0.0216 (4)
C261.05438 (15)0.14745 (11)0.89758 (11)0.0230 (4)
H541.04730.12790.94780.028*
C271.08270 (16)0.23684 (12)0.90993 (12)0.0281 (5)
H321.09020.25900.86140.034*
H331.02440.26510.92120.034*
C281.18724 (17)0.25026 (13)0.97816 (13)0.0363 (5)
H341.20530.30700.98150.044*
H351.17660.23461.02780.044*
C291.27954 (18)0.20260 (14)0.96696 (14)0.0410 (6)
H361.34270.20901.01350.049*
H371.29690.22350.92140.049*
C301.25193 (17)0.11356 (14)0.95408 (14)0.0399 (6)
H381.24320.09101.00210.048*
H391.31080.08550.94330.048*
C311.14817 (16)0.10098 (13)0.88463 (13)0.0330 (5)
H401.15910.11890.83570.040*
H411.13070.04410.87930.040*
C320.90634 (15)0.02306 (10)0.81022 (12)0.0215 (4)
H550.95890.00510.78490.026*
C330.93034 (16)0.02350 (11)0.88812 (12)0.0251 (4)
H421.00160.00960.92330.030*
H430.87800.00970.91440.030*
C340.92479 (17)0.11331 (11)0.86989 (13)0.0304 (5)
H440.98050.12710.84680.037*
H450.93870.14320.91910.037*
C350.81590 (18)0.13772 (12)0.81309 (14)0.0360 (5)
H460.76100.12960.83850.043*
H470.81720.19440.80060.043*
C360.78722 (18)0.08883 (12)0.73637 (13)0.0348 (5)
H480.83610.10280.70720.042*
H490.71460.10220.70340.042*
C370.79441 (16)0.00105 (11)0.75349 (12)0.0272 (5)
H500.73980.01620.77720.033*
H510.78080.03050.70410.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01625 (8)0.01725 (7)0.01517 (8)0.00036 (6)0.00515 (6)0.00109 (6)
Cl10.0337 (3)0.0213 (2)0.0204 (2)0.0042 (2)0.0148 (2)0.00410 (19)
P10.0186 (3)0.0176 (2)0.0161 (2)0.0007 (2)0.0053 (2)0.0002 (2)
P20.0161 (3)0.0211 (2)0.0207 (3)0.0011 (2)0.0061 (2)0.0003 (2)
Si10.0205 (3)0.0190 (3)0.0187 (3)0.0035 (2)0.0064 (2)0.0012 (2)
C10.0316 (12)0.0236 (10)0.0297 (12)0.0045 (9)0.0107 (10)0.0014 (9)
C20.0255 (11)0.0183 (9)0.0193 (10)0.0037 (8)0.0044 (9)0.0020 (8)
C30.0347 (13)0.0292 (11)0.0298 (12)0.0027 (10)0.0109 (10)0.0082 (9)
C40.0419 (14)0.0309 (12)0.0272 (12)0.0014 (10)0.0017 (11)0.0127 (10)
C50.0265 (12)0.0231 (11)0.0326 (12)0.0001 (9)0.0036 (10)0.0058 (9)
C60.0231 (11)0.0189 (10)0.0267 (11)0.0027 (8)0.0024 (9)0.0011 (8)
C70.0222 (11)0.0154 (9)0.0176 (10)0.0031 (8)0.0011 (8)0.0011 (8)
C80.0214 (11)0.0232 (10)0.0210 (10)0.0033 (8)0.0061 (9)0.0021 (8)
C90.0300 (12)0.0215 (10)0.0256 (11)0.0009 (9)0.0060 (9)0.0022 (9)
C100.0425 (14)0.0274 (11)0.0311 (13)0.0017 (10)0.0050 (11)0.0088 (10)
C110.0397 (14)0.0345 (12)0.0229 (12)0.0097 (10)0.0045 (10)0.0087 (10)
C120.0416 (14)0.0419 (12)0.0272 (12)0.0029 (11)0.0168 (11)0.0060 (10)
C130.0358 (13)0.0292 (11)0.0238 (11)0.0013 (9)0.0131 (10)0.0045 (9)
C140.0203 (10)0.0191 (9)0.0172 (10)0.0016 (8)0.0057 (8)0.0019 (8)
C150.0273 (12)0.0290 (11)0.0277 (12)0.0050 (9)0.0117 (10)0.0074 (9)
C160.0365 (14)0.0293 (12)0.0452 (15)0.0061 (10)0.0159 (12)0.0109 (10)
C170.0303 (13)0.0286 (11)0.0441 (14)0.0079 (10)0.0050 (11)0.0037 (10)
C180.0215 (12)0.0310 (12)0.0491 (15)0.0013 (9)0.0124 (11)0.0019 (11)
C190.0246 (12)0.0252 (11)0.0373 (13)0.0008 (9)0.0101 (10)0.0024 (9)
C200.0188 (10)0.0222 (9)0.0209 (10)0.0100 (8)0.0066 (8)0.0022 (8)
C210.0254 (11)0.0264 (11)0.0247 (11)0.0108 (9)0.0076 (9)0.0001 (9)
C220.0366 (13)0.0384 (12)0.0207 (11)0.0174 (10)0.0148 (10)0.0062 (10)
C230.0347 (13)0.0370 (12)0.0333 (13)0.0086 (10)0.0204 (11)0.0107 (10)
C240.0279 (12)0.0300 (11)0.0314 (12)0.0028 (9)0.0136 (10)0.0031 (9)
C250.0188 (10)0.0242 (10)0.0224 (11)0.0070 (8)0.0073 (8)0.0042 (8)
C260.0169 (10)0.0290 (11)0.0223 (11)0.0028 (8)0.0052 (8)0.0017 (9)
C270.0244 (12)0.0331 (11)0.0254 (11)0.0080 (9)0.0059 (9)0.0007 (9)
C280.0318 (13)0.0416 (13)0.0305 (13)0.0158 (11)0.0028 (10)0.0012 (10)
C290.0215 (12)0.0575 (15)0.0391 (14)0.0117 (11)0.0029 (10)0.0053 (12)
C300.0193 (12)0.0512 (15)0.0452 (15)0.0008 (10)0.0045 (11)0.0044 (12)
C310.0185 (11)0.0411 (12)0.0384 (13)0.0007 (10)0.0077 (10)0.0019 (11)
C320.0179 (10)0.0189 (9)0.0288 (11)0.0020 (8)0.0090 (9)0.0009 (8)
C330.0204 (11)0.0249 (10)0.0303 (12)0.0029 (8)0.0083 (9)0.0032 (9)
C340.0281 (12)0.0252 (11)0.0419 (14)0.0055 (9)0.0167 (11)0.0069 (10)
C350.0350 (14)0.0211 (11)0.0535 (16)0.0028 (10)0.0162 (12)0.0007 (10)
C360.0293 (13)0.0284 (11)0.0436 (14)0.0053 (10)0.0073 (11)0.0077 (10)
C370.0220 (11)0.0255 (10)0.0318 (12)0.0007 (9)0.0055 (9)0.0004 (9)
Geometric parameters (Å, º) top
Pd1—P22.3132 (6)C17—H260.9700
Pd1—Cl12.4584 (6)C17—H270.9700
P1—Pd12.3111 (7)C18—C191.531 (3)
P1—C81.8421 (18)C18—H280.9700
P1—C141.8468 (19)C18—H290.9700
P2—C261.847 (2)C19—H300.9700
P2—C321.8480 (18)C19—H310.9700
Si1—C21.888 (2)C20—C211.398 (3)
Si1—C11.893 (2)C20—C251.402 (3)
Si1—C201.8942 (19)C21—C221.384 (3)
Si1—Pd12.2829 (6)C21—H50.9300
C1—H90.9600C22—C231.374 (3)
C1—H100.9600C22—H60.9300
C1—H110.9600C23—C241.383 (3)
C2—C31.397 (3)C23—H70.9300
C2—C71.406 (2)C24—C251.402 (3)
C3—C41.381 (3)C24—H80.9300
C3—H10.9300C25—P21.8370 (19)
C4—C51.389 (3)C26—C311.528 (3)
C4—H20.9300C26—C271.531 (3)
C5—C61.378 (3)C26—H540.9800
C5—H30.9300C27—C281.527 (3)
C6—C71.403 (3)C27—H320.9700
C6—H40.9300C27—H330.9700
C7—P11.8307 (19)C28—C291.509 (3)
C8—C131.520 (3)C28—H340.9700
C8—C91.529 (3)C28—H350.9700
C8—H520.9800C29—C301.524 (3)
C9—C101.542 (3)C29—H360.9700
C9—H120.9700C29—H370.9700
C9—H130.9700C30—C311.530 (3)
C10—C111.505 (3)C30—H380.9700
C10—H140.9700C30—H390.9700
C10—H150.9700C31—H400.9700
C11—C121.522 (3)C31—H410.9700
C11—H160.9700C32—C331.527 (3)
C11—H170.9700C32—C371.534 (3)
C12—C131.526 (3)C32—H550.9800
C12—H180.9700C33—C341.525 (3)
C12—H190.9700C33—H420.9700
C13—H200.9700C33—H430.9700
C13—H210.9700C34—C351.515 (3)
C14—C191.518 (3)C34—H440.9700
C14—C151.527 (2)C34—H450.9700
C14—H530.9800C35—C361.526 (3)
C15—C161.523 (3)C35—H460.9700
C15—H220.9700C35—H470.9700
C15—H230.9700C36—C371.522 (3)
C16—C171.518 (3)C36—H480.9700
C16—H240.9700C36—H490.9700
C16—H250.9700C37—H500.9700
C17—C181.510 (3)C37—H510.9700
Si1—Pd1—P183.42 (3)C18—C17—H27109.6
Si1—Pd1—P283.56 (3)C16—C17—H27109.6
P1—Pd1—P2160.56 (4)H26—C17—H27108.1
Si1—Pd1—Cl1178.18 (4)C17—C18—C19110.74 (16)
P1—Pd1—Cl194.96 (3)C17—C18—H28109.5
P2—Pd1—Cl198.21 (3)C19—C18—H28109.5
C7—P1—C8105.23 (9)C17—C18—H29109.5
C7—P1—C14105.22 (9)C19—C18—H29109.5
C8—P1—C14105.40 (8)H28—C18—H29108.1
C7—P1—Pd1111.50 (7)C14—C19—C18111.10 (16)
C8—P1—Pd1121.38 (7)C14—C19—H30109.4
C14—P1—Pd1106.91 (6)C18—C19—H30109.4
C25—P2—C26108.15 (9)C14—C19—H31109.4
C25—P2—C32102.06 (9)C18—C19—H31109.4
C26—P2—C32104.38 (9)H30—C19—H31108.0
C25—P2—Pd1109.19 (7)C21—C20—C25118.34 (17)
C26—P2—Pd1116.74 (6)C21—C20—Si1125.34 (15)
C32—P2—Pd1115.13 (6)C25—C20—Si1116.30 (13)
C2—Si1—C1101.56 (9)C22—C21—C20120.99 (19)
C2—Si1—C20115.16 (9)C22—C21—H5119.5
C1—Si1—C20106.97 (8)C20—C21—H5119.5
C2—Si1—Pd1109.23 (6)C23—C22—C21120.20 (19)
C1—Si1—Pd1116.79 (7)C23—C22—H6119.9
C20—Si1—Pd1107.38 (6)C21—C22—H6119.9
Si1—C1—H9109.5C22—C23—C24120.45 (19)
Si1—C1—H10109.5C22—C23—H7119.8
H9—C1—H10109.5C24—C23—H7119.8
Si1—C1—H11109.5C23—C24—C25119.8 (2)
H9—C1—H11109.5C23—C24—H8120.1
H10—C1—H11109.5C25—C24—H8120.1
C3—C2—C7117.83 (18)C20—C25—C24120.16 (17)
C3—C2—Si1125.42 (15)C20—C25—P2116.34 (13)
C7—C2—Si1115.93 (14)C24—C25—P2123.40 (15)
C4—C3—C2121.47 (19)C31—C26—C27110.10 (16)
C4—C3—H1119.3C31—C26—P2116.21 (14)
C2—C3—H1119.3C27—C26—P2110.93 (13)
C3—C4—C5120.39 (19)C31—C26—H54106.3
C3—C4—H2119.8C27—C26—H54106.3
C5—C4—H2119.8P2—C26—H54106.3
C6—C5—C4119.32 (19)C28—C27—C26111.73 (17)
C6—C5—H3120.3C28—C27—H32109.3
C4—C5—H3120.3C26—C27—H32109.3
C5—C6—C7120.75 (18)C28—C27—H33109.3
C5—C6—H4119.6C26—C27—H33109.3
C7—C6—H4119.6H32—C27—H33107.9
C6—C7—C2120.12 (17)C29—C28—C27111.77 (19)
C6—C7—P1124.00 (14)C29—C28—H34109.3
C2—C7—P1115.87 (14)C27—C28—H34109.3
C13—C8—C9110.58 (17)C29—C28—H35109.3
C13—C8—P1112.19 (13)C27—C28—H35109.3
C9—C8—P1110.38 (13)H34—C28—H35107.9
C13—C8—H52107.8C28—C29—C30111.63 (18)
C9—C8—H52107.8C28—C29—H36109.3
P1—C8—H52107.8C30—C29—H36109.3
C8—C9—C10110.66 (16)C28—C29—H37109.3
C8—C9—H12109.5C30—C29—H37109.3
C10—C9—H12109.5H36—C29—H37108.0
C8—C9—H13109.5C29—C30—C31111.15 (19)
C10—C9—H13109.5C29—C30—H38109.4
H12—C9—H13108.1C31—C30—H38109.4
C11—C10—C9111.78 (16)C29—C30—H39109.4
C11—C10—H14109.3C31—C30—H39109.4
C9—C10—H14109.3H38—C30—H39108.0
C11—C10—H15109.3C26—C31—C30111.02 (18)
C9—C10—H15109.3C26—C31—H40109.4
H14—C10—H15107.9C30—C31—H40109.4
C10—C11—C12111.33 (18)C26—C31—H41109.4
C10—C11—H16109.4C30—C31—H41109.4
C12—C11—H16109.4H40—C31—H41108.0
C10—C11—H17109.4C33—C32—C37110.56 (16)
C12—C11—H17109.4C33—C32—P2114.83 (13)
H16—C11—H17108.0C37—C32—P2110.73 (13)
C11—C12—C13111.58 (17)C33—C32—H55106.7
C11—C12—H18109.3C37—C32—H55106.7
C13—C12—H18109.3P2—C32—H55106.7
C11—C12—H19109.3C34—C33—C32108.82 (16)
C13—C12—H19109.3C34—C33—H42109.9
H18—C12—H19108.0C32—C33—H42109.9
C8—C13—C12110.77 (16)C34—C33—H43109.9
C8—C13—H20109.5C32—C33—H43109.9
C12—C13—H20109.5H42—C33—H43108.3
C8—C13—H21109.5C35—C34—C33112.01 (17)
C12—C13—H21109.5C35—C34—H44109.2
H20—C13—H21108.1C33—C34—H44109.2
C19—C14—C15109.61 (16)C35—C34—H45109.2
C19—C14—P1116.73 (13)C33—C34—H45109.2
C15—C14—P1109.12 (12)H44—C34—H45107.9
C19—C14—H53107.0C34—C35—C36111.27 (17)
C15—C14—H53107.0C34—C35—H46109.4
P1—C14—H53107.0C36—C35—H46109.4
C16—C15—C14111.76 (16)C34—C35—H47109.4
C16—C15—H22109.3C36—C35—H47109.4
C14—C15—H22109.3H46—C35—H47108.0
C16—C15—H23109.3C37—C36—C35111.30 (18)
C14—C15—H23109.3C37—C36—H48109.4
H22—C15—H23107.9C35—C36—H48109.4
C17—C16—C15111.14 (17)C37—C36—H49109.4
C17—C16—H24109.4C35—C36—H49109.4
C15—C16—H24109.4H48—C36—H49108.0
C17—C16—H25109.4C36—C37—C32110.54 (16)
C15—C16—H25109.4C36—C37—H50109.5
H24—C16—H25108.0C32—C37—H50109.5
C18—C17—C16110.28 (19)C36—C37—H51109.5
C18—C17—H26109.6C32—C37—H51109.5
C16—C17—H26109.6H50—C37—H51108.1
Si1—Pd1—P2—C2521.40 (7)C3—C4—C5—C62.6 (3)
P1—Pd1—P2—C2526.82 (9)C4—C5—C6—C70.1 (3)
Cl1—Pd1—P2—C25159.00 (6)C5—C6—C7—C22.8 (3)
Si1—Pd1—P2—C26101.61 (7)C5—C6—C7—P1176.37 (15)
P1—Pd1—P2—C26149.83 (8)C3—C2—C7—C63.1 (3)
Cl1—Pd1—P2—C2677.98 (7)Si1—C2—C7—C6167.11 (14)
Si1—Pd1—P2—C32135.46 (7)C3—C2—C7—P1176.15 (14)
P1—Pd1—P2—C3287.24 (9)Si1—C2—C7—P113.66 (19)
Cl1—Pd1—P2—C3244.95 (7)C6—C7—P1—C848.12 (18)
C7—P1—Pd1—Si111.09 (6)C2—C7—P1—C8132.68 (15)
C8—P1—Pd1—Si1113.73 (7)C6—C7—P1—C1462.93 (17)
C14—P1—Pd1—Si1125.58 (6)C2—C7—P1—C14116.27 (15)
C7—P1—Pd1—P237.14 (9)C6—C7—P1—Pd1178.46 (14)
C8—P1—Pd1—P2161.96 (8)C2—C7—P1—Pd10.74 (16)
C14—P1—Pd1—P277.35 (8)C13—C8—C9—C1056.2 (2)
C7—P1—Pd1—Cl1169.74 (6)P1—C8—C9—C10179.03 (13)
C8—P1—Pd1—Cl165.44 (7)C8—C9—C10—C1155.2 (2)
C14—P1—Pd1—Cl155.25 (6)C9—C10—C11—C1254.3 (2)
C7—P1—C8—C13163.86 (14)C10—C11—C12—C1355.0 (2)
C14—P1—C8—C1352.94 (16)C9—C8—C13—C1257.1 (2)
Pd1—P1—C8—C1368.48 (15)P1—C8—C13—C12179.20 (15)
C7—P1—C8—C972.32 (15)C11—C12—C13—C856.4 (2)
C14—P1—C8—C9176.75 (13)C19—C14—C15—C1655.6 (2)
Pd1—P1—C8—C955.33 (15)P1—C14—C15—C16175.45 (15)
C7—P1—C14—C1961.00 (16)C14—C15—C16—C1756.0 (2)
C8—P1—C14—C1949.93 (16)C15—C16—C17—C1856.3 (2)
Pd1—P1—C14—C19179.66 (13)C16—C17—C18—C1957.3 (2)
C7—P1—C14—C1563.90 (15)C15—C14—C19—C1856.5 (2)
C8—P1—C14—C15174.84 (13)P1—C14—C19—C18178.88 (14)
Pd1—P1—C14—C1554.76 (14)C17—C18—C19—C1458.3 (2)
C25—P2—C26—C3158.80 (16)C25—C20—C21—C220.2 (3)
C32—P2—C26—C3149.33 (16)Si1—C20—C21—C22178.54 (15)
Pd1—P2—C26—C31177.66 (12)C20—C21—C22—C231.1 (3)
C25—P2—C26—C2767.95 (14)C21—C22—C23—C241.1 (3)
C32—P2—C26—C27176.08 (13)C22—C23—C24—C250.3 (3)
Pd1—P2—C26—C2755.59 (14)C21—C20—C25—C241.6 (3)
C25—P2—C32—C33161.75 (14)Si1—C20—C25—C24177.30 (15)
C26—P2—C32—C3349.19 (15)C21—C20—C25—P2174.99 (14)
Pd1—P2—C32—C3380.12 (14)Si1—C20—C25—P26.1 (2)
C25—P2—C32—C3772.17 (15)C23—C24—C25—C201.6 (3)
C26—P2—C32—C37175.27 (13)C23—C24—C25—P2174.71 (15)
Pd1—P2—C32—C3745.96 (15)C20—C25—P2—C26114.32 (15)
C2—Si1—Pd1—P116.64 (6)C24—C25—P2—C2669.22 (18)
C1—Si1—Pd1—P197.81 (8)C20—C25—P2—C32135.96 (15)
C20—Si1—Pd1—P1142.15 (7)C24—C25—P2—C3240.50 (19)
C2—Si1—Pd1—P2148.89 (6)C20—C25—P2—Pd113.67 (16)
C1—Si1—Pd1—P296.66 (8)C24—C25—P2—Pd1162.79 (15)
C20—Si1—Pd1—P223.38 (6)C31—C26—C27—C2855.6 (2)
C1—Si1—C2—C367.68 (18)P2—C26—C27—C28174.39 (14)
C20—Si1—C2—C347.5 (2)C26—C27—C28—C2954.7 (2)
Pd1—Si1—C2—C3168.37 (15)C27—C28—C29—C3054.0 (3)
C1—Si1—C2—C7101.67 (15)C28—C29—C30—C3155.0 (3)
C20—Si1—C2—C7143.16 (14)C27—C26—C31—C3056.5 (2)
Pd1—Si1—C2—C722.28 (16)P2—C26—C31—C30176.32 (14)
C2—Si1—C20—C2136.01 (19)C29—C30—C31—C2656.5 (2)
C1—Si1—C20—C2176.01 (18)C37—C32—C33—C3458.93 (19)
Pd1—Si1—C20—C21157.89 (15)P2—C32—C33—C34174.90 (13)
C2—Si1—C20—C25145.19 (14)C32—C33—C34—C3557.9 (2)
C1—Si1—C20—C25102.80 (15)C33—C34—C35—C3655.7 (2)
Pd1—Si1—C20—C2523.30 (16)C34—C35—C36—C3753.8 (2)
C7—C2—C3—C40.6 (3)C35—C36—C37—C3255.2 (2)
Si1—C2—C3—C4168.58 (16)C33—C32—C37—C3658.4 (2)
C2—C3—C4—C52.3 (3)P2—C32—C37—C36173.13 (14)

Experimental details

Crystal data
Chemical formula[Pd(C37H55P2Si)Cl]
Mr731.69
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)13.079 (3), 16.632 (3), 17.739 (4)
β (°) 108.55 (3)
V3)3658.3 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.73
Crystal size (mm)0.49 × 0.4 × 0.4
Data collection
DiffractometerBruker P4
diffractometer
Absorption correctionMulti-scan
(CrystalClear, Rigaku, 2005)
Tmin, Tmax0.690, 0.758
No. of measured, independent and
observed [I > 2σ(I)] reflections
26471, 8379, 6612
Rint0.029
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.059, 0.93
No. of reflections8379
No. of parameters380
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.83, 0.24

Computer programs: CrystalClear, Rigaku, 2005, CrystalStructure (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Pd1—P22.3132 (6)P1—Pd12.3111 (7)
Pd1—Cl12.4584 (6)Si1—Pd12.2829 (6)
Si1—Pd1—P183.42 (3)Si1—Pd1—Cl1178.18 (4)
Si1—Pd1—P283.56 (3)P1—Pd1—Cl194.96 (3)
P1—Pd1—P2160.56 (4)P2—Pd1—Cl198.21 (3)
 

Acknowledgements

The authors are grateful to the Starter Fund of Southeast University for financial support to buy the CCD X-ray diffractometer.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBoom, M. E. van der & Milstein, D. (2003). Chem. Rev. 103, 1759–1792.  Web of Science CrossRef PubMed Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationMoulton, C. J. & Shaw, B. L. (1976). J. Chem. Soc. Dalton Trans. pp. 1020–1024.  CrossRef Web of Science Google Scholar
First citationRigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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