supplementary materials


wm2316 scheme

Acta Cryst. (2010). E66, m522    [ doi:10.1107/S160053681001319X ]

Bis{1-[2-(diphenylphosphino)ethyl]-3-ethylimidazol-2-ylidene}palladium(II) bis(hexafluoridophosphate) acetonitrile 2.85-solvate

A. A. Aziza, U. Flörke, H. Egold and G. Henkel

Abstract top

In the structure of the title compound, [Pd(C19H21N2P)2](PF6)2·2.85CH3CN, the two six-membered NHC-phosphane chelate rings form a distorted square-planar coordination geometry around the PdII atom, which lies 0.212 (1) Å above the coordination plane. The sum of the bond angles at PdII is 358.3°, with C-Pd-P bite angles of 84.03 (10) and 83.54 (9)°. The structure includes three acetonitrile solvent molecules, one with partial site occupation and one with severe disorder, which was eventually excluded from the refinement.

Comment top

The two six-membered NHC-phosphane chelate rings form a distorted square-planar coordination geometry around the palladium(II) atom which lies 0.212 (1) Å above the coordination plane. The sum of bond angles at Pd is 358.3° with C1—Pd1—P1 and C31—Pd1—P2 bite angles of 84.03 (10)° and 83.54 (9)°, respectively. The trans C1—Pd1—C31 and P1—Pd1—P2 bond angles are 173.56 (13)° and 164.44 (3)° and thus deviate clearly from linearity. The Pd—C bond lengths (2.031 (3) and 2.033 (3) Å) are within the expected range and the Pd—P bond lengths of 2.3085 (9) and 2.3100 (9) Å also are comparable to those in other complexes containing Pd-NHC phosphane ligands (e.g. Chiu et al. (2005); Lee et al. (2004a,b); Navarro et al. (2004); Tsoureas et al. (2003)). There are no intermolecular contacts shorter than the van der Waals distances.

Related literature top

For the structures of related PdII complexes, see: Chiu et al. (2005); Lee et al. (2004a,b); Navarro et al. (2004); Tsoureas et al. (2003). For refinement aspects, see: Spek (2009).

Experimental top

To a solution of 3-[2-(diphenylphosphino)ethyl]-1-ethylimidazolium-hexafluoridophosphate (195 mg, 0.46 mmol) in THF (10 ml) was added KN(SiMe3)2 (118 mg, 0.46 mmol + 30%) and the mixture was stirred at room temperature under N2 for 30 min. Then [Pd(COD)Cl2] (66 mg, 0.230 mmol; COD = 1,5-cyclooctadiene) was added to the reaction mixture and the colour changed from pale yellow to yellow–orange. The reaction mixture was stirred for another 2 h and then the solvent was removed under vacuum. Yellow crystals were obtained from an acetonitrile solution by diethyl ether diffusion.

Refinement top

For the final refinement, data were cut off at θ = 27.1° in order to get 99% completeness. H atoms were clearly identified in difference Fourier syntheses, idealized and refined at calculated positions riding on the C atoms with isotropic displacement parameters Uiso(H) = 1.2U(Ceq) or 1.5U(-CH3). All methyl H atoms were allowed to rotate but not to tip. There are three acetonitrile solvent molecules per asymmetric unit. Two of these could be refined easily, the N300 one with an occupation factor of 0.85 (1). It was, however, not possible to refine successfully the third heavily distorted acetonitrile molecule. After treatment of the data with the SQUEEZE facility of PLATON (Spek, 2009) refinement then proceeded smoothly.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. For clarity, the N300 solvent molecule with partial site occupation was omitted.
Bis{1-[2-(diphenylphosphino)ethyl]-3-ethyl-imidazol-2-ylidene}palladium(II) bis(hexafluoridophosphate) acetonitrile 2.85-solvate top
Crystal data top
[Pd(C19H21N2P)2](PF6)2·2.85C2H3NZ = 2
Mr = 1130.45F(000) = 1150
Triclinic, P1Dx = 1.519 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.114 (2) ÅCell parameters from 1002 reflections
b = 11.343 (2) Åθ = 2.3–28.1°
c = 20.243 (4) ŵ = 0.59 mm1
α = 77.490 (4)°T = 120 K
β = 83.580 (5)°Prism, pale-yellow
γ = 85.301 (4)°0.42 × 0.20 × 0.20 mm
V = 2471.4 (8) Å3
Data collection top
Bruker SMART APEX
diffractometer
10802 independent reflections
Radiation source: sealed tube9025 reflections with I > 2σ(I)
graphiteRint = 0.032
φ and ω scansθmax = 27.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1414
Tmin = 0.790, Tmax = 0.891k = 1414
20500 measured reflectionsl = 2425
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)] = 0.047Hydrogen site location: difference Fourier map
wR(F2) = 0.129H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0605P)2 + 3.077P]
where P = (Fo2 + 2Fc2)/3
10802 reflections(Δ/σ)max < 0.001
584 parametersΔρmax = 0.90 e Å3
0 restraintsΔρmin = 0.56 e Å3
Crystal data top
[Pd(C19H21N2P)2](PF6)2·2.85C2H3Nγ = 85.301 (4)°
Mr = 1130.45V = 2471.4 (8) Å3
Triclinic, P1Z = 2
a = 11.114 (2) ÅMo Kα radiation
b = 11.343 (2) ŵ = 0.59 mm1
c = 20.243 (4) ÅT = 120 K
α = 77.490 (4)°0.42 × 0.20 × 0.20 mm
β = 83.580 (5)°
Data collection top
Bruker SMART APEX
diffractometer
10802 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
9025 reflections with I > 2σ(I)
Tmin = 0.790, Tmax = 0.891Rint = 0.032
20500 measured reflectionsθmax = 27.1°
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.129Δρmax = 0.90 e Å3
S = 1.05Δρmin = 0.56 e Å3
10802 reflectionsAbsolute structure: ?
584 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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 > 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*/UeqOcc. (<1)
Pd10.14297 (2)0.58147 (2)0.214403 (12)0.01778 (8)
P10.10291 (8)0.69609 (8)0.29654 (4)0.02250 (19)
P20.14709 (8)0.50588 (8)0.11694 (4)0.02037 (18)
N10.0082 (3)0.3656 (3)0.29190 (14)0.0242 (6)
N20.1052 (3)0.5386 (3)0.28212 (14)0.0233 (6)
N30.3767 (3)0.7229 (2)0.16884 (14)0.0216 (6)
N40.2425 (2)0.7651 (2)0.09788 (14)0.0215 (6)
C10.0041 (3)0.4847 (3)0.26744 (16)0.0220 (7)
C20.0877 (4)0.2695 (3)0.28886 (19)0.0318 (8)
H2A0.16300.30580.26530.038*
H2B0.06330.21360.26210.038*
C30.1126 (4)0.1990 (4)0.3589 (2)0.0424 (10)
H3A0.17640.13540.35470.064*
H3B0.03840.16220.38220.064*
H3C0.13900.25370.38510.064*
C40.1260 (3)0.3454 (3)0.32047 (17)0.0280 (8)
H4A0.15780.26920.34060.034*
C50.1863 (3)0.4538 (3)0.31420 (17)0.0256 (7)
H5A0.26910.46920.32900.031*
C60.1331 (3)0.6692 (3)0.26246 (18)0.0267 (7)
H6A0.22080.68680.27380.032*
H6B0.11520.69550.21260.032*
C70.0607 (3)0.7417 (3)0.2980 (2)0.0299 (8)
H7A0.09540.73290.34590.036*
H7B0.07030.82840.27590.036*
C110.1811 (3)0.8350 (3)0.2794 (2)0.0301 (8)
C120.2725 (4)0.8492 (4)0.3179 (2)0.0412 (10)
H12A0.28860.78950.35720.049*
C130.3400 (5)0.9504 (5)0.2990 (3)0.0581 (14)
H13A0.40100.96120.32610.070*
C140.3197 (5)1.0347 (4)0.2416 (3)0.0620 (16)
H14A0.36781.10300.22850.074*
C150.2303 (4)1.0217 (4)0.2027 (3)0.0551 (14)
H15A0.21681.08100.16280.066*
C160.1588 (4)0.9219 (3)0.2213 (2)0.0396 (10)
H16A0.09600.91350.19480.047*
C210.1273 (3)0.6228 (3)0.38290 (17)0.0273 (7)
C220.0872 (4)0.6806 (4)0.4361 (2)0.0399 (10)
H22A0.04650.75850.42700.048*
C230.1068 (5)0.6240 (6)0.5024 (2)0.0529 (13)
H23A0.08020.66350.53870.063*
C240.1641 (5)0.5121 (5)0.5151 (2)0.0538 (13)
H24A0.17560.47330.56060.065*
C250.2059 (5)0.4536 (5)0.4633 (2)0.0493 (12)
H25A0.24680.37580.47310.059*
C260.1879 (4)0.5092 (4)0.39648 (19)0.0352 (9)
H26A0.21670.46970.36040.042*
C310.2673 (3)0.6927 (3)0.15747 (16)0.0200 (6)
C320.4479 (3)0.6611 (3)0.22448 (18)0.0294 (8)
H32A0.39630.60510.25810.035*
H32B0.47420.72160.24770.035*
C330.5575 (3)0.5912 (3)0.1988 (2)0.0334 (8)
H33A0.60260.55040.23710.050*
H33B0.60960.64680.16640.050*
H33C0.53150.53080.17610.050*
C340.4190 (3)0.8157 (3)0.11711 (18)0.0263 (7)
H34A0.49340.85340.11390.032*
C350.3350 (3)0.8424 (3)0.07238 (18)0.0257 (7)
H35A0.33840.90230.03150.031*
C360.1317 (3)0.7596 (3)0.06651 (18)0.0252 (7)
H36A0.12860.82490.02530.030*
H36B0.06050.77320.09860.030*
C370.1246 (4)0.6381 (3)0.04706 (17)0.0281 (8)
H37A0.18690.63190.00880.034*
H37B0.04430.63540.03080.034*
C410.0274 (3)0.4071 (3)0.11525 (17)0.0230 (7)
C420.0919 (3)0.4487 (3)0.13059 (17)0.0267 (7)
H42A0.10880.53000.13560.032*
C430.1864 (3)0.3721 (4)0.13863 (19)0.0322 (8)
H43A0.26740.40030.14990.039*
C440.1616 (4)0.2546 (4)0.13016 (19)0.0352 (9)
H44A0.22570.20160.13650.042*
C450.0438 (4)0.2132 (3)0.1125 (2)0.0353 (9)
H45A0.02760.13300.10560.042*
C460.0501 (4)0.2903 (3)0.10514 (19)0.0287 (8)
H46A0.13070.26240.09300.034*
C510.2878 (3)0.4266 (3)0.09389 (17)0.0238 (7)
C520.3191 (4)0.4080 (4)0.0279 (2)0.0356 (9)
H52A0.26690.43950.00670.043*
C530.4262 (4)0.3436 (4)0.0130 (2)0.0443 (10)
H53A0.44680.33110.03190.053*
C540.5031 (4)0.2975 (4)0.0622 (2)0.0396 (10)
H54A0.57630.25340.05130.047*
C550.4740 (4)0.3153 (3)0.1277 (2)0.0335 (8)
H55A0.52740.28430.16170.040*
C560.3655 (3)0.3792 (3)0.14365 (18)0.0262 (7)
H56A0.34480.39030.18880.031*
P100.78890 (8)0.89315 (8)0.08279 (5)0.0250 (2)
F110.7426 (2)1.03165 (19)0.07981 (13)0.0408 (6)
F120.8351 (2)0.7545 (2)0.08694 (13)0.0425 (6)
F130.6962 (2)0.8529 (2)0.14901 (11)0.0391 (5)
F140.6869 (2)0.8796 (2)0.03586 (12)0.0380 (5)
F150.8896 (2)0.9069 (2)0.13115 (12)0.0383 (5)
F160.8808 (2)0.9332 (2)0.01755 (12)0.0446 (6)
P200.49733 (11)0.28058 (11)0.35088 (6)0.0413 (3)
F210.5132 (3)0.4160 (3)0.35538 (17)0.0684 (9)
F220.6133 (3)0.2418 (3)0.38990 (17)0.0776 (10)
F230.5813 (3)0.3003 (3)0.28115 (14)0.0584 (7)
F240.3828 (3)0.3256 (5)0.31074 (19)0.1052 (15)
F250.4106 (3)0.2649 (4)0.42035 (17)0.0807 (11)
F260.4822 (5)0.1461 (4)0.3489 (3)0.134 (2)
N2000.8799 (7)0.0600 (8)0.3056 (6)0.149 (4)
C2010.7923 (8)0.0335 (5)0.2890 (4)0.083 (2)
C2020.6818 (7)0.0013 (7)0.2705 (4)0.095 (2)
H20A0.66390.08040.29560.143*
H20B0.68950.00320.22150.143*
H20C0.61580.05890.28140.143*
N3000.6186 (8)0.7019 (8)0.3728 (4)0.115 (4)0.852 (11)
C3010.5552 (7)0.6772 (10)0.4114 (4)0.094 (3)0.852 (11)
C3020.4552 (18)0.6296 (16)0.4684 (10)0.226 (9)*0.852 (11)
H30A0.42540.69410.49240.340*0.852 (11)
H30B0.48880.56060.50040.340*0.852 (11)
H30C0.38800.60410.44830.340*0.852 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01780 (13)0.02025 (13)0.01547 (12)0.00351 (9)0.00124 (9)0.00340 (9)
P10.0217 (4)0.0254 (4)0.0219 (4)0.0036 (3)0.0001 (3)0.0083 (3)
P20.0215 (4)0.0236 (4)0.0166 (4)0.0023 (3)0.0028 (3)0.0046 (3)
N10.0255 (16)0.0276 (14)0.0201 (14)0.0059 (12)0.0026 (11)0.0044 (11)
N20.0201 (15)0.0308 (15)0.0194 (14)0.0036 (12)0.0037 (11)0.0046 (11)
N30.0177 (14)0.0252 (14)0.0219 (14)0.0021 (11)0.0013 (11)0.0048 (11)
N40.0154 (14)0.0252 (14)0.0220 (14)0.0003 (11)0.0003 (11)0.0018 (11)
C10.0240 (17)0.0262 (16)0.0161 (15)0.0055 (13)0.0041 (13)0.0026 (12)
C20.036 (2)0.0240 (17)0.033 (2)0.0044 (15)0.0054 (16)0.0044 (15)
C30.040 (2)0.040 (2)0.041 (2)0.0041 (18)0.0026 (19)0.0013 (18)
C40.0293 (19)0.0350 (19)0.0197 (16)0.0143 (15)0.0004 (14)0.0025 (14)
C50.0194 (17)0.0381 (19)0.0191 (16)0.0084 (14)0.0014 (13)0.0029 (14)
C60.0195 (17)0.0313 (18)0.0280 (18)0.0004 (14)0.0037 (14)0.0037 (14)
C70.0233 (19)0.0316 (18)0.037 (2)0.0020 (14)0.0004 (15)0.0144 (16)
C110.0280 (19)0.0268 (17)0.038 (2)0.0044 (15)0.0049 (16)0.0161 (15)
C120.039 (2)0.041 (2)0.049 (3)0.0104 (19)0.0021 (19)0.0183 (19)
C130.051 (3)0.045 (3)0.085 (4)0.019 (2)0.001 (3)0.025 (3)
C140.055 (3)0.029 (2)0.103 (5)0.016 (2)0.015 (3)0.020 (3)
C150.042 (3)0.029 (2)0.085 (4)0.0002 (19)0.010 (3)0.000 (2)
C160.041 (2)0.0262 (18)0.048 (2)0.0008 (17)0.0039 (19)0.0055 (17)
C210.0233 (18)0.040 (2)0.0210 (17)0.0080 (15)0.0005 (14)0.0111 (15)
C220.031 (2)0.061 (3)0.032 (2)0.0025 (19)0.0003 (17)0.021 (2)
C230.046 (3)0.093 (4)0.025 (2)0.013 (3)0.0034 (19)0.025 (2)
C240.051 (3)0.088 (4)0.023 (2)0.019 (3)0.0053 (19)0.005 (2)
C250.054 (3)0.056 (3)0.037 (2)0.009 (2)0.014 (2)0.001 (2)
C260.038 (2)0.043 (2)0.0251 (19)0.0060 (18)0.0043 (16)0.0071 (16)
C310.0152 (15)0.0223 (15)0.0224 (16)0.0003 (12)0.0001 (12)0.0059 (13)
C320.029 (2)0.0331 (18)0.0267 (18)0.0038 (15)0.0117 (15)0.0027 (15)
C330.0221 (19)0.035 (2)0.041 (2)0.0003 (15)0.0095 (16)0.0027 (17)
C340.0209 (17)0.0271 (17)0.0292 (18)0.0048 (14)0.0022 (14)0.0031 (14)
C350.0190 (17)0.0252 (16)0.0294 (18)0.0053 (13)0.0014 (14)0.0013 (14)
C360.0231 (18)0.0273 (17)0.0237 (17)0.0033 (14)0.0059 (14)0.0006 (13)
C370.035 (2)0.0307 (18)0.0183 (16)0.0052 (15)0.0068 (14)0.0004 (14)
C410.0206 (17)0.0292 (17)0.0208 (16)0.0055 (13)0.0052 (13)0.0056 (13)
C420.0280 (19)0.0326 (18)0.0224 (17)0.0025 (15)0.0049 (14)0.0108 (14)
C430.0185 (18)0.050 (2)0.0310 (19)0.0053 (16)0.0038 (15)0.0132 (17)
C440.037 (2)0.040 (2)0.0292 (19)0.0187 (18)0.0048 (16)0.0021 (16)
C450.045 (2)0.0256 (18)0.036 (2)0.0063 (16)0.0165 (18)0.0016 (15)
C460.0286 (19)0.0278 (17)0.0307 (19)0.0002 (14)0.0114 (15)0.0046 (14)
C510.0209 (17)0.0302 (17)0.0222 (16)0.0044 (14)0.0019 (13)0.0090 (14)
C520.033 (2)0.050 (2)0.0253 (19)0.0013 (18)0.0042 (16)0.0124 (17)
C530.042 (3)0.058 (3)0.035 (2)0.004 (2)0.0067 (19)0.021 (2)
C540.023 (2)0.050 (2)0.047 (2)0.0045 (17)0.0025 (17)0.019 (2)
C550.0247 (19)0.036 (2)0.042 (2)0.0003 (15)0.0078 (16)0.0120 (17)
C560.0204 (17)0.0314 (18)0.0274 (18)0.0026 (14)0.0020 (14)0.0076 (14)
P100.0195 (4)0.0224 (4)0.0318 (5)0.0031 (3)0.0055 (4)0.0006 (4)
F110.0470 (15)0.0263 (11)0.0493 (14)0.0035 (10)0.0139 (12)0.0057 (10)
F120.0409 (14)0.0265 (11)0.0612 (16)0.0034 (10)0.0146 (12)0.0085 (11)
F130.0283 (12)0.0513 (14)0.0342 (12)0.0092 (10)0.0001 (10)0.0005 (10)
F140.0313 (12)0.0439 (13)0.0414 (13)0.0072 (10)0.0152 (10)0.0065 (10)
F150.0304 (12)0.0381 (12)0.0483 (14)0.0049 (10)0.0179 (10)0.0049 (10)
F160.0357 (14)0.0526 (15)0.0412 (14)0.0110 (11)0.0058 (11)0.0023 (11)
P200.0336 (6)0.0489 (6)0.0426 (6)0.0133 (5)0.0027 (5)0.0088 (5)
F210.079 (2)0.0559 (18)0.070 (2)0.0091 (16)0.0168 (17)0.0225 (16)
F220.060 (2)0.099 (3)0.061 (2)0.0021 (18)0.0164 (16)0.0151 (18)
F230.0574 (18)0.0743 (19)0.0451 (16)0.0043 (15)0.0051 (13)0.0207 (14)
F240.045 (2)0.204 (5)0.070 (2)0.003 (2)0.0208 (17)0.031 (3)
F250.064 (2)0.102 (3)0.064 (2)0.0207 (19)0.0251 (17)0.0010 (19)
F260.142 (4)0.080 (3)0.194 (5)0.070 (3)0.053 (4)0.070 (3)
N2000.083 (5)0.134 (7)0.256 (12)0.020 (5)0.010 (6)0.094 (7)
C2010.107 (6)0.046 (3)0.090 (5)0.000 (4)0.019 (4)0.018 (3)
C2020.083 (5)0.089 (5)0.125 (7)0.010 (4)0.006 (5)0.053 (5)
N3000.104 (6)0.121 (7)0.088 (5)0.024 (5)0.051 (5)0.008 (5)
C3010.053 (5)0.179 (10)0.059 (5)0.013 (5)0.005 (4)0.047 (6)
Geometric parameters (Å, °) top
Pd1—C312.031 (3)C32—C331.504 (5)
Pd1—C12.033 (3)C32—H32A0.9900
Pd1—P12.3085 (9)C32—H32B0.9900
Pd1—P22.3100 (9)C33—H33A0.9800
P1—C211.806 (4)C33—H33B0.9800
P1—C111.811 (4)C33—H33C0.9800
P1—C71.848 (4)C34—C351.344 (5)
P2—C511.805 (4)C34—H34A0.9500
P2—C411.815 (3)C35—H35A0.9500
P2—C371.847 (3)C36—C371.523 (5)
N1—C11.347 (4)C36—H36A0.9900
N1—C41.387 (5)C36—H36B0.9900
N1—C21.467 (5)C37—H37A0.9900
N2—C11.347 (5)C37—H37B0.9900
N2—C51.379 (4)C41—C461.383 (5)
N2—C61.466 (4)C41—C421.395 (5)
N3—C311.348 (4)C42—C431.391 (5)
N3—C341.386 (4)C42—H42A0.9500
N3—C321.467 (4)C43—C441.381 (6)
N4—C311.347 (4)C43—H43A0.9500
N4—C351.387 (4)C44—C451.389 (6)
N4—C361.459 (4)C44—H44A0.9500
C2—C31.512 (6)C45—C461.391 (5)
C2—H2A0.9900C45—H45A0.9500
C2—H2B0.9900C46—H46A0.9500
C3—H3A0.9800C51—C561.391 (5)
C3—H3B0.9800C51—C521.400 (5)
C3—H3C0.9800C52—C531.383 (6)
C4—C51.339 (5)C52—H52A0.9500
C4—H4A0.9500C53—C541.375 (6)
C5—H5A0.9500C53—H53A0.9500
C6—C71.528 (5)C54—C551.382 (6)
C6—H6A0.9900C54—H54A0.9500
C6—H6B0.9900C55—C561.397 (5)
C7—H7A0.9900C55—H55A0.9500
C7—H7B0.9900C56—H56A0.9500
C11—C121.386 (6)P10—F161.584 (2)
C11—C161.392 (6)P10—F141.595 (2)
C12—C131.384 (6)P10—F121.601 (2)
C12—H12A0.9500P10—F131.603 (2)
C13—C141.362 (8)P10—F111.603 (2)
C13—H13A0.9500P10—F151.605 (2)
C14—C151.371 (8)P20—F261.558 (4)
C14—H14A0.9500P20—F221.569 (3)
C15—C161.396 (6)P20—F241.577 (4)
C15—H15A0.9500P20—F211.583 (3)
C16—H16A0.9500P20—F231.586 (3)
C21—C221.391 (5)P20—F251.598 (3)
C21—C261.392 (6)N200—C2011.147 (10)
C22—C231.390 (6)C201—C2021.421 (11)
C22—H22A0.9500C202—H20A0.9800
C23—C241.359 (8)C202—H20B0.9800
C23—H23A0.9500C202—H20C0.9800
C24—C251.378 (7)N300—C3011.000 (9)
C24—H24A0.9500C301—C3021.549 (19)
C25—C261.391 (6)C302—H30A0.9800
C25—H25A0.9500C302—H30B0.9800
C26—H26A0.9500C302—H30C0.9800
C31—Pd1—C1173.56 (13)C33—C32—H32B109.4
C31—Pd1—P194.24 (9)H32A—C32—H32B108.0
C1—Pd1—P184.03 (10)C32—C33—H33A109.5
C31—Pd1—P283.54 (9)C32—C33—H33B109.5
C1—Pd1—P296.46 (10)H33A—C33—H33B109.5
P1—Pd1—P2164.44 (3)C32—C33—H33C109.5
C21—P1—C11105.73 (18)H33A—C33—H33C109.5
C21—P1—C7105.68 (18)H33B—C33—H33C109.5
C11—P1—C7106.11 (17)C35—C34—N3107.0 (3)
C21—P1—Pd1117.44 (13)C35—C34—H34A126.5
C11—P1—Pd1115.02 (12)N3—C34—H34A126.5
C7—P1—Pd1105.96 (12)C34—C35—N4106.4 (3)
C51—P2—C41106.27 (16)C34—C35—H35A126.8
C51—P2—C37107.06 (17)N4—C35—H35A126.8
C41—P2—C37105.51 (16)N4—C36—C37111.9 (3)
C51—P2—Pd1115.17 (11)N4—C36—H36A109.2
C41—P2—Pd1115.95 (11)C37—C36—H36A109.2
C37—P2—Pd1106.15 (12)N4—C36—H36B109.2
C1—N1—C4110.3 (3)C37—C36—H36B109.2
C1—N1—C2125.6 (3)H36A—C36—H36B107.9
C4—N1—C2124.1 (3)C36—C37—P2114.2 (2)
C1—N2—C5110.7 (3)C36—C37—H37A108.7
C1—N2—C6123.4 (3)P2—C37—H37A108.7
C5—N2—C6125.8 (3)C36—C37—H37B108.7
C31—N3—C34110.5 (3)P2—C37—H37B108.7
C31—N3—C32125.8 (3)H37A—C37—H37B107.6
C34—N3—C32123.5 (3)C46—C41—C42119.2 (3)
C31—N4—C35110.9 (3)C46—C41—P2123.0 (3)
C31—N4—C36122.6 (3)C42—C41—P2117.6 (3)
C35—N4—C36126.5 (3)C43—C42—C41120.5 (3)
N1—C1—N2105.3 (3)C43—C42—H42A119.8
N1—C1—Pd1133.2 (3)C41—C42—H42A119.8
N2—C1—Pd1121.5 (2)C44—C43—C42119.5 (4)
N1—C2—C3111.9 (3)C44—C43—H43A120.2
N1—C2—H2A109.2C42—C43—H43A120.2
C3—C2—H2A109.2C43—C44—C45120.7 (4)
N1—C2—H2B109.2C43—C44—H44A119.7
C3—C2—H2B109.2C45—C44—H44A119.7
H2A—C2—H2B107.9C44—C45—C46119.3 (4)
C2—C3—H3A109.5C44—C45—H45A120.3
C2—C3—H3B109.5C46—C45—H45A120.3
H3A—C3—H3B109.5C41—C46—C45120.8 (4)
C2—C3—H3C109.5C41—C46—H46A119.6
H3A—C3—H3C109.5C45—C46—H46A119.6
H3B—C3—H3C109.5C56—C51—C52119.0 (3)
C5—C4—N1106.9 (3)C56—C51—P2119.1 (3)
C5—C4—H4A126.6C52—C51—P2121.9 (3)
N1—C4—H4A126.6C53—C52—C51119.9 (4)
C4—C5—N2106.9 (3)C53—C52—H52A120.0
C4—C5—H5A126.6C51—C52—H52A120.0
N2—C5—H5A126.6C54—C53—C52120.9 (4)
N2—C6—C7112.6 (3)C54—C53—H53A119.5
N2—C6—H6A109.1C52—C53—H53A119.5
C7—C6—H6A109.1C53—C54—C55120.0 (4)
N2—C6—H6B109.1C53—C54—H54A120.0
C7—C6—H6B109.1C55—C54—H54A120.0
H6A—C6—H6B107.8C54—C55—C56119.7 (4)
C6—C7—P1114.3 (2)C54—C55—H55A120.1
C6—C7—H7A108.7C56—C55—H55A120.1
P1—C7—H7A108.7C51—C56—C55120.4 (3)
C6—C7—H7B108.7C51—C56—H56A119.8
P1—C7—H7B108.7C55—C56—H56A119.8
H7A—C7—H7B107.6F16—P10—F1490.43 (14)
C12—C11—C16119.9 (4)F16—P10—F1290.52 (14)
C12—C11—P1121.1 (3)F14—P10—F1290.56 (13)
C16—C11—P1118.5 (3)F16—P10—F13179.76 (15)
C13—C12—C11119.8 (5)F14—P10—F1389.78 (13)
C13—C12—H12A120.1F12—P10—F1389.59 (14)
C11—C12—H12A120.1F16—P10—F1190.12 (14)
C14—C13—C12120.4 (5)F14—P10—F1189.97 (13)
C14—C13—H13A119.8F12—P10—F11179.17 (14)
C12—C13—H13A119.8F13—P10—F1189.78 (14)
C13—C14—C15120.4 (4)F16—P10—F1590.59 (14)
C13—C14—H14A119.8F14—P10—F15178.91 (14)
C15—C14—H14A119.8F12—P10—F1589.80 (13)
C14—C15—C16120.5 (5)F13—P10—F1589.20 (13)
C14—C15—H15A119.8F11—P10—F1589.66 (13)
C16—C15—H15A119.8F26—P20—F2290.2 (3)
C11—C16—C15118.9 (5)F26—P20—F2492.2 (3)
C11—C16—H16A120.5F22—P20—F24177.4 (3)
C15—C16—H16A120.5F26—P20—F21178.2 (3)
C22—C21—C26119.7 (4)F22—P20—F2188.5 (2)
C22—C21—P1120.1 (3)F24—P20—F2189.0 (2)
C26—C21—P1120.2 (3)F26—P20—F2391.7 (2)
C23—C22—C21119.9 (5)F22—P20—F2389.29 (18)
C23—C22—H22A120.1F24—P20—F2389.78 (19)
C21—C22—H22A120.1F21—P20—F2389.62 (17)
C24—C23—C22119.8 (4)F26—P20—F2589.6 (2)
C24—C23—H23A120.1F22—P20—F2591.9 (2)
C22—C23—H23A120.1F24—P20—F2588.9 (2)
C23—C24—C25121.4 (4)F21—P20—F2589.04 (19)
C23—C24—H24A119.3F23—P20—F25178.2 (2)
C25—C24—H24A119.3N200—C201—C202178.2 (9)
C24—C25—C26119.5 (5)C201—C202—H20A109.5
C24—C25—H25A120.2C201—C202—H20B109.5
C26—C25—H25A120.2H20A—C202—H20B109.5
C25—C26—C21119.6 (4)C201—C202—H20C109.5
C25—C26—H26A120.2H20A—C202—H20C109.5
C21—C26—H26A120.2H20B—C202—H20C109.5
N4—C31—N3105.2 (3)N300—C301—C302175.1 (14)
N4—C31—Pd1121.4 (2)C301—C302—H30A109.5
N3—C31—Pd1133.0 (2)C301—C302—H30B109.5
N3—C32—C33111.4 (3)H30A—C302—H30B109.5
N3—C32—H32A109.4C301—C302—H30C109.5
C33—C32—H32A109.4H30A—C302—H30C109.5
N3—C32—H32B109.4H30B—C302—H30C109.5
C31—Pd1—P1—C21121.77 (16)Pd1—P1—C21—C2611.0 (4)
C1—Pd1—P1—C2164.46 (16)C26—C21—C22—C230.6 (6)
P2—Pd1—P1—C21157.10 (16)P1—C21—C22—C23179.7 (3)
C31—Pd1—P1—C113.65 (18)C21—C22—C23—C240.6 (7)
C1—Pd1—P1—C11170.13 (18)C22—C23—C24—C251.4 (8)
P2—Pd1—P1—C1177.49 (19)C23—C24—C25—C260.9 (7)
C31—Pd1—P1—C7120.51 (16)C24—C25—C26—C210.3 (7)
C1—Pd1—P1—C753.27 (16)C22—C21—C26—C251.0 (6)
P2—Pd1—P1—C739.38 (19)P1—C21—C26—C25179.9 (3)
C31—Pd1—P2—C5167.33 (16)C35—N4—C31—N31.1 (4)
C1—Pd1—P2—C51119.15 (16)C36—N4—C31—N3178.9 (3)
P1—Pd1—P2—C51149.91 (16)C35—N4—C31—Pd1173.0 (2)
C31—Pd1—P2—C41167.71 (16)C36—N4—C31—Pd17.0 (4)
C1—Pd1—P2—C415.81 (16)C34—N3—C31—N41.2 (4)
P1—Pd1—P2—C4185.13 (17)C32—N3—C31—N4173.9 (3)
C31—Pd1—P2—C3750.94 (16)C34—N3—C31—Pd1171.9 (3)
C1—Pd1—P2—C37122.58 (16)C32—N3—C31—Pd113.0 (5)
P1—Pd1—P2—C3731.64 (19)P1—Pd1—C31—N4107.3 (3)
C4—N1—C1—N21.3 (4)P2—Pd1—C31—N457.2 (3)
C2—N1—C1—N2179.1 (3)P1—Pd1—C31—N364.8 (3)
C4—N1—C1—Pd1175.5 (3)P2—Pd1—C31—N3130.6 (3)
C2—N1—C1—Pd14.1 (5)C31—N3—C32—C33108.9 (4)
C5—N2—C1—N11.3 (4)C34—N3—C32—C3365.6 (4)
C6—N2—C1—N1178.1 (3)C31—N3—C34—C350.8 (4)
C5—N2—C1—Pd1175.9 (2)C32—N3—C34—C35174.4 (3)
C6—N2—C1—Pd10.9 (4)N3—C34—C35—N40.1 (4)
P1—Pd1—C1—N1130.2 (3)C31—N4—C35—C340.6 (4)
P2—Pd1—C1—N165.4 (3)C36—N4—C35—C34179.4 (3)
P1—Pd1—C1—N253.4 (3)C31—N4—C36—C3763.7 (4)
P2—Pd1—C1—N2110.9 (3)C35—N4—C36—C37116.4 (4)
C1—N1—C2—C3120.2 (4)N4—C36—C37—P252.2 (4)
C4—N1—C2—C360.2 (5)C51—P2—C37—C36113.4 (3)
C1—N1—C4—C50.8 (4)C41—P2—C37—C36133.7 (3)
C2—N1—C4—C5179.6 (3)Pd1—P2—C37—C3610.2 (3)
N1—C4—C5—N20.1 (4)C51—P2—C41—C466.3 (3)
C1—N2—C5—C40.9 (4)C37—P2—C41—C46119.8 (3)
C6—N2—C5—C4177.6 (3)Pd1—P2—C41—C46123.1 (3)
C1—N2—C6—C765.3 (4)C51—P2—C41—C42179.2 (3)
C5—N2—C6—C7118.4 (4)C37—P2—C41—C4265.8 (3)
N2—C6—C7—P146.9 (4)Pd1—P2—C41—C4251.4 (3)
C21—P1—C7—C6109.5 (3)C46—C41—C42—C432.8 (5)
C11—P1—C7—C6138.5 (3)P2—C41—C42—C43171.8 (3)
Pd1—P1—C7—C615.8 (3)C41—C42—C43—C441.1 (5)
C21—P1—C11—C1220.4 (4)C42—C43—C44—C451.2 (6)
C7—P1—C11—C12132.4 (3)C43—C44—C45—C461.6 (6)
Pd1—P1—C11—C12110.9 (3)C42—C41—C46—C452.4 (5)
C21—P1—C11—C16167.6 (3)P2—C41—C46—C45172.0 (3)
C7—P1—C11—C1655.7 (3)C44—C45—C46—C410.2 (6)
Pd1—P1—C11—C1661.1 (3)C41—P2—C51—C56107.9 (3)
C16—C11—C12—C130.8 (6)C37—P2—C51—C56139.7 (3)
P1—C11—C12—C13172.6 (4)Pd1—P2—C51—C5621.9 (3)
C11—C12—C13—C141.8 (7)C41—P2—C51—C5269.9 (3)
C12—C13—C14—C151.4 (8)C37—P2—C51—C5242.5 (4)
C13—C14—C15—C160.0 (8)Pd1—P2—C51—C52160.2 (3)
C12—C11—C16—C150.6 (6)C56—C51—C52—C530.2 (6)
P1—C11—C16—C15171.4 (3)P2—C51—C52—C53178.1 (3)
C14—C15—C16—C111.0 (7)C51—C52—C53—C540.2 (7)
C11—P1—C21—C2260.2 (3)C52—C53—C54—C550.1 (7)
C7—P1—C21—C2252.0 (3)C53—C54—C55—C560.7 (6)
Pd1—P1—C21—C22169.9 (3)C52—C51—C56—C550.8 (5)
C11—P1—C21—C26118.9 (3)P2—C51—C56—C55178.8 (3)
C7—P1—C21—C26128.9 (3)C54—C55—C56—C511.1 (6)
Table 1
Selected geometric parameters (Å, °)
top
Pd1—C312.031 (3)Pd1—P12.3085 (9)
Pd1—C12.033 (3)Pd1—P22.3100 (9)
C31—Pd1—C1173.56 (13)C31—Pd1—P283.54 (9)
C31—Pd1—P194.24 (9)C1—Pd1—P296.46 (10)
C1—Pd1—P184.03 (10)P1—Pd1—P2164.44 (3)
references
References top

Bruker (2002). SMART, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Chiu, P. L., Lai, C. L., Chang, C. F., Hu, C. H. & Lee, H. M. (2005). Organometallics, 24, 6169–6178.

Lee, H. M., Chiu, P. L. & Zeng, J. Y. (2004a). Inorg. Chim. Acta, 357, 4313–4321.

Lee, H. M., Zeng, J. Y., Hu, C.-H. & Lee, M.-T. (2004b). Inorg. Chem. 43, 6822–6829.

Navarro, O., Kaur, H., Mahjoor, P. & Nolan, S. P. (2004). J. Org. Chem. 69, 3171–3180.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Tsoureas, N., Danpoulos, A. A., Tulloch, A. A. D. & Light, M. E. (2003). Organometallics, 22, 4750–4758.