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

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ISSN: 2056-9890

Aceto­nitrile­[2-(1-{bis­­[2,4,6-tris­­(tri­fluoro­meth­yl)phen­yl]phosphan­yl­oxy}-1-methyl­eth­yl)pyridine]­methyl­palladium(II) hexa­fluorido­anti­monate di­chloro­methane hemisolvate

aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and bDepartment of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA
*Correspondence e-mail: haoay@sdu.edu.cn

(Received 23 December 2010; accepted 12 February 2011; online 23 February 2011)

In the title compound, [Pd(CH3)(C26H14F18NOP)(C2H3N)][SbF6]·0.5CH2Cl2, the Pd2+ cation has a distorted square-planar environment, being coordinated by the acetonitrile [Pd—N = 2.078 (8) Å] and methyl [Pd—C = 2.052 (9) Å] groups and the bidentate ligand 2-(1-{bis­[2,4,6-tris­(trifluoro­meth­yl)phen­yl]phosphan­yloxy}-1-methyl­eth­yl)pyridine (L). In L, one –CF3 group is rotationally disordered between two orientations in a 1:1 ratio. The solvent mol­ecule was treated as disordered between two positions related by an inversion center with occupancies fixed at 0.5. The crystal packing exhibits weak inter­molecular C—H⋯F contacts.

Related literature

For general background to the chemistry of phosphine-imine ligands and palladium complexes, see: Batsanov et al. (2002[Batsanov, A., Cornet, S. M., Dillon, K. B., Goeta, A. E., Hazendonk, P. & Thompson, A. L. (2002). J. Chem. Soc. Dalton Trans. pp. 4622-4628.]); Chen et al. (2003[Chen, H.-P., Liu, Y.-H., Peng, S.-M. & Liu, S.-T. (2003). Organometallics, 22, 4893-4899.]); Doherty et al. (2007[Doherty, M. D., Trudeau, S., White, P. S., Morken, J. P. & Brookhart, M. S. (2007). Organometallics, 26, 1261-1269.]); Flapper et al. (2009a[Flapper, J., Kooijman, H., Lutz, M., Spek, A. L., van Leeuwen, P. W. N. M., Elsevier, C. J. & Kamer, P. C. J. (2009a). Organometallics, 28, 3272-3281.],b[Flapper, J., van Leeuwen, P. W. N. M., Elsevier, C. J. & Kamer, P. C. J. (2009b). Organometallics, 28, 3264-3271.]); Guan & Marshall (2002[Guan, Z. & Marshall, W. J. (2002). Organometallics, 21, 3580-3586.]); Kermagoret & Braunstein (2008[Kermagoret, A. & Braunstein, P. (2008). Organometallics, 27, 88-99.]); Speiser et al. (2004[Speiser, F., Braunstein, P., Saussine, L. & Welter, R. (2004). Inorg. Chem. 43, 1649-1658.]).

[Scheme 1]

Experimental

Crystal data
  • [Pd(CH3)(C26H14F18NOP)(C2H3N)][SbF6]·0.5CH2Cl2

  • Mr = 1170.05

  • Triclinic, [P \overline 1]

  • a = 8.8635 (8) Å

  • b = 12.1336 (12) Å

  • c = 19.107 (2) Å

  • α = 79.166 (8)°

  • β = 80.147 (8)°

  • γ = 78.266 (8)°

  • V = 1957.2 (3) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 11.56 mm−1

  • T = 100 K

  • 0.15 × 0.10 × 0.05 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: numerical (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.276, Tmax = 0.596

  • 12653 measured reflections

  • 6232 independent reflections

  • 4802 reflections with I > 2σ(I)

  • Rint = 0.052

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.191

  • S = 1.02

  • 6232 reflections

  • 590 parameters

  • 63 restraints

  • H-atom parameters constrained

  • Δρmax = 2.34 e Å−3

  • Δρmin = −0.95 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4B⋯F1i 0.98 2.40 3.365 (13) 166
C12—H12⋯F5i 0.95 2.60 3.276 (11) 129
C4—H4A⋯F4 0.98 2.53 3.464 (13) 158
C4—H4C⋯F2ii 0.98 2.30 3.225 (13) 155
C11—H11C⋯F5iii 0.98 2.49 3.352 (11) 146
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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

The oligomerization of ethylene is one of the most important industrial processes to obtain linear alpha-olefins (Chen et al., 2003; Guan et al.,2002). Bidentate phosphine-imine ligands (P^N ligands) have attracted considerable concerns in the field of transition metal catalysis. Palladium and nickel complexes with P^N ligands have been widely applied in the oligomerization and polymerization of ethylene(Doherty et al., 2007; Flapper et al., 2009a,b; Kermagoret et al., 2008; Speiser et al., 2004). Herein, we report the synthesis and characterization of cationic palladium complex, with electron-poor bulky ligand bearing tris(trifluoromethyl) phenyl phosphine, which can be synthesized according to the literature (Batsanov et al., 2002; Speiser et al., 2004), [(CH3N)(CH3)LPd]+ [SbF6]- 0.5(CH2Cl2), where L = [2-ethyl-(1'-methyl-1'-oxy(bis(2,4,6-tris(trifluoromethyl) phenyl)phosphino)]pyridine.

In the title compound, each Pd center has a distorted square-planar environment being coordinated by acetonitrile [Pd—N 2.078 (8) Å], methyl [Pd—C 2.052 (9) Å] and bidentate ligand L. In L, one CF3 group is rotationally disordered between two orientations in a ratio 1:1. The solvent molecule has been treated as disordered between two positions related by inversion center with occupancies fixed to 0.5 each. The crystal packing exhibits weak intermolecular C—H···F contacts (Table 1).

Related literature top

For general background to the chemistry of phosphine-imine ligands and palladium complexes, see: Batsanov et al. (2002); Chen et al. (2003); Doherty et al. (2007); Flapper et al. (2009a,b); Guan et al. (2002); Kermagoret et al. (2008); Speiser et al. (2004).

Experimental top

All manipulations of air- and/or moisture-sensitive compounds were conducted using standard Schlenk techniques. Argon was purified by passage through columns of BASF R3–11 catalyst (Chemalog) and 4Å molecular sieves. All solvents were deoxygenated, dried and distilled using common techniques. 2-Pyridin-2-ylpropan-2-ol and di[tris(trifluoromethyl)phenyl]phosphine chloride were prepared according to the literature procedures(Batsanov et al., 2002; Speiser et al., 2004). A flame-dried Schlenk flask was charged with 2-pyridin-2-ylpropan-2-ol (280 mg, 1.30 mmol) and dried THF (5 ml). The solution was cooled to -78°C, and 2.5 mol/l n-BuLi in hexane (0.52 ml, 1.30 mmol) was added slowly. After stirring of 2.0 hrs at -78°C, 800 mg in THF(2 ml) was added slowly. Stirring for 1 day, 30 ml degassed saturated NaCl solution was charged for hydrolysis. After separation, dry and column purification, the ligand of 2-ethyl-[1'-methyl-1'-oxy(di(2, 4, 6-tris(trifluoromethyl) phenyl)phosphino)] pyridine was obtained. The cationic complex was prepared by reaction of the above ligand (1.0 equiv.), (COD)PdMeCl (1.0 equiv.), and AgSbF6 (1.0 equiv.) at RT, and the single-crystal was cultivated by recrystallization of CH2Cl2 and pentane. Calcd for C29H20F24N2OPPdSb: C, 30.89; H, 1.79; N, 2.48. Found: C, 30.89; H, 1.59; N, 2.21.

Refinement top

All H atoms were geometrically positioned (C—H 0.95-0.99 Å) and refined as riding, with Uiso(H) = 1.2-1.5 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (I) showing the atom-numbering scheme and 50% probabilty displacement ellipsoids. Only one part of the disordered CF3 group is shown. The H atoms and solvent molecules were omitted for clarity.
Acetonitrile[2-(1-{bis[2,4,6-tris(trifluoromethyl)phenyl]phosphanyloxy}- 1-methylethyl)pyridine]methylpalladium(II) hexafluoridoantimonate dichloromethane hemisolvate top
Crystal data top
[Pd(CH3)(C26H14F18NOP)(C2H3N)][SbF6]·0.5CH2Cl2Z = 2
Mr = 1170.05F(000) = 1130
Triclinic, P1Dx = 1.985 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 8.8635 (8) ÅCell parameters from 3085 reflections
b = 12.1336 (12) Åθ = 2.4–66.3°
c = 19.107 (2) ŵ = 11.56 mm1
α = 79.166 (8)°T = 100 K
β = 80.147 (8)°Prism, colourless
γ = 78.266 (8)°0.15 × 0.10 × 0.05 mm
V = 1957.2 (3) Å3
Data collection top
Bruker APEXII CCD
diffractometer
6232 independent reflections
Radiation source: fine-focus sealed tube4802 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ϕ and ω scansθmax = 67.3°, θmin = 2.4°
Absorption correction: numerical
(SADABS; Bruker, 2007)
h = 1010
Tmin = 0.276, Tmax = 0.596k = 1413
12653 measured reflectionsl = 2222
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1096P)2 + 11.4198P]
where P = (Fo2 + 2Fc2)/3
6232 reflections(Δ/σ)max < 0.001
590 parametersΔρmax = 2.34 e Å3
63 restraintsΔρmin = 0.95 e Å3
Crystal data top
[Pd(CH3)(C26H14F18NOP)(C2H3N)][SbF6]·0.5CH2Cl2γ = 78.266 (8)°
Mr = 1170.05V = 1957.2 (3) Å3
Triclinic, P1Z = 2
a = 8.8635 (8) ÅCu Kα radiation
b = 12.1336 (12) ŵ = 11.56 mm1
c = 19.107 (2) ÅT = 100 K
α = 79.166 (8)°0.15 × 0.10 × 0.05 mm
β = 80.147 (8)°
Data collection top
Bruker APEXII CCD
diffractometer
6232 independent reflections
Absorption correction: numerical
(SADABS; Bruker, 2007)
4802 reflections with I > 2σ(I)
Tmin = 0.276, Tmax = 0.596Rint = 0.052
12653 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06663 restraints
wR(F2) = 0.191H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1096P)2 + 11.4198P]
where P = (Fo2 + 2Fc2)/3
6232 reflectionsΔρmax = 2.34 e Å3
590 parametersΔρmin = 0.95 e Å3
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*/UeqOcc. (<1)
Pd10.39331 (7)0.28306 (5)0.20297 (4)0.0287 (2)
P10.2317 (2)0.17257 (18)0.26378 (12)0.0271 (5)
C10.3238 (12)0.3978 (8)0.2736 (5)0.038 (2)
H1A0.41540.41360.28960.058*
H1B0.25610.36580.31530.058*
H1C0.26680.46870.24960.058*
C30.5856 (11)0.4644 (8)0.1041 (6)0.035 (2)
C40.6566 (13)0.5542 (9)0.0576 (6)0.044 (2)
H4A0.58300.62650.05690.066*
H4B0.68420.53570.00870.066*
H4C0.75070.56120.07570.066*
N50.5278 (9)0.3961 (7)0.1395 (4)0.0329 (17)
O60.1387 (7)0.1455 (5)0.2067 (3)0.0279 (13)
C70.2062 (10)0.1351 (8)0.1295 (5)0.0293 (19)
C80.3807 (10)0.0855 (8)0.1224 (5)0.0290 (19)
N90.4740 (9)0.1537 (7)0.1327 (4)0.0301 (16)
C100.1082 (11)0.0593 (9)0.1097 (5)0.035 (2)
H10A0.00230.08950.12270.052*
H10B0.13360.01820.13580.052*
H10C0.13020.05780.05780.052*
C110.1809 (11)0.2512 (8)0.0820 (5)0.034 (2)
H11A0.22970.24400.03260.052*
H11B0.22770.30470.10030.052*
H11C0.06910.27960.08250.052*
C120.6264 (10)0.1235 (8)0.1163 (5)0.0307 (19)
H120.69130.17440.12090.037*
C130.6963 (11)0.0210 (9)0.0926 (5)0.037 (2)
H130.80620.00180.08150.045*
C140.6010 (12)0.0513 (9)0.0857 (5)0.038 (2)
H140.64430.12370.07190.046*
C150.4404 (12)0.0178 (8)0.0991 (5)0.036 (2)
H150.37270.06520.09230.044*
C160.0614 (11)0.2221 (7)0.3317 (5)0.032 (2)
C170.0542 (11)0.1885 (8)0.4067 (5)0.032 (2)
C180.0813 (12)0.2128 (8)0.4534 (6)0.038 (2)
H180.08230.18750.50370.045*
C190.2166 (12)0.2743 (9)0.4271 (6)0.040 (2)
C200.2084 (11)0.3147 (8)0.3550 (6)0.036 (2)
H200.29840.36040.33720.043*
C210.0762 (11)0.2923 (8)0.3076 (6)0.034 (2)
C220.1891 (12)0.1192 (9)0.4428 (6)0.039 (2)
C230.3671 (13)0.2958 (11)0.4782 (6)0.049 (3)
C240.0904 (11)0.3491 (8)0.2309 (6)0.037 (2)
F250.1962 (7)0.0064 (5)0.4459 (3)0.0479 (15)
F260.3246 (6)0.1442 (5)0.4090 (3)0.0425 (13)
F270.1776 (8)0.1381 (6)0.5101 (3)0.0548 (17)
F280.346 (2)0.323 (2)0.5373 (11)0.081 (5)0.50
F290.4321 (18)0.1986 (15)0.4936 (10)0.068 (4)0.50
F300.4754 (19)0.3697 (17)0.4483 (9)0.070 (4)0.50
F28A0.354 (2)0.2539 (18)0.5459 (9)0.072 (5)0.50
F29A0.476 (3)0.263 (3)0.4619 (14)0.103 (7)0.50
F30A0.411 (2)0.4029 (17)0.4800 (12)0.091 (6)0.50
F310.1953 (7)0.4478 (5)0.2306 (3)0.0470 (15)
F320.1387 (7)0.2859 (5)0.1925 (3)0.0404 (13)
F330.0422 (6)0.3815 (5)0.1958 (3)0.0382 (12)
C340.3269 (10)0.0207 (8)0.2948 (5)0.0274 (18)
C350.4889 (11)0.0100 (8)0.2957 (5)0.033 (2)
C360.5675 (12)0.1170 (9)0.2856 (5)0.041 (2)
H360.67710.13420.28510.049*
C370.4903 (13)0.1995 (8)0.2763 (6)0.043 (3)
C380.3305 (13)0.1775 (9)0.2834 (6)0.041 (2)
H380.27570.23600.28110.049*
C390.2482 (12)0.0697 (8)0.2941 (5)0.035 (2)
C400.5991 (11)0.0602 (9)0.3100 (6)0.039 (2)
C410.5765 (16)0.3156 (10)0.2601 (8)0.060 (4)
C420.0767 (12)0.0694 (8)0.3098 (5)0.037 (2)
F430.5466 (7)0.1693 (5)0.3180 (3)0.0430 (13)
F440.7231 (7)0.0620 (6)0.2587 (3)0.0486 (15)
F450.6537 (7)0.0103 (6)0.3723 (3)0.0490 (15)
F460.7237 (11)0.3168 (7)0.2408 (8)0.121 (5)
F470.5548 (11)0.3967 (6)0.3154 (5)0.080 (3)
F480.5253 (16)0.3471 (8)0.2071 (6)0.114 (4)
F490.0470 (7)0.1512 (5)0.3669 (3)0.0488 (15)
F500.0170 (7)0.0935 (5)0.2562 (3)0.0456 (14)
F510.0107 (6)0.0275 (5)0.3278 (3)0.0381 (13)
Sb10.13293 (7)0.70526 (5)0.07820 (4)0.0384 (2)
F10.2407 (9)0.5556 (5)0.0969 (4)0.0581 (18)
F20.0566 (8)0.6539 (8)0.0901 (4)0.068 (2)
F30.0296 (10)0.8560 (6)0.0551 (5)0.078 (3)
F40.3226 (8)0.7596 (7)0.0633 (5)0.071 (2)
F50.1630 (7)0.6941 (6)0.0202 (3)0.0465 (14)
F60.1099 (11)0.7165 (9)0.1756 (4)0.085 (3)
C520.026 (3)0.411 (3)0.6363 (14)0.077 (8)0.50
H52A0.01070.34780.67660.093*0.50
H52B0.03130.47930.65620.093*0.50
Cl10.1188 (19)0.4375 (15)0.5867 (9)0.169 (6)0.50
Cl20.190 (2)0.374 (3)0.5796 (15)0.273 (13)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0282 (3)0.0193 (3)0.0379 (4)0.0050 (3)0.0009 (3)0.0052 (3)
P10.0243 (10)0.0179 (10)0.0382 (12)0.0025 (9)0.0017 (9)0.0058 (9)
C10.048 (6)0.025 (5)0.043 (5)0.006 (4)0.002 (4)0.014 (4)
C30.031 (5)0.023 (5)0.050 (6)0.001 (4)0.001 (4)0.014 (4)
C40.050 (6)0.025 (5)0.054 (6)0.013 (5)0.008 (5)0.006 (4)
N50.029 (4)0.023 (4)0.046 (4)0.008 (4)0.003 (3)0.002 (3)
O60.023 (3)0.023 (3)0.038 (3)0.002 (2)0.001 (2)0.008 (2)
C70.030 (4)0.033 (5)0.027 (4)0.007 (4)0.004 (3)0.007 (4)
C80.029 (4)0.028 (5)0.030 (4)0.004 (4)0.000 (3)0.008 (4)
N90.032 (4)0.029 (4)0.027 (4)0.001 (3)0.000 (3)0.009 (3)
C100.028 (4)0.038 (5)0.043 (5)0.006 (4)0.001 (4)0.020 (4)
C110.031 (5)0.034 (5)0.037 (5)0.002 (4)0.007 (4)0.005 (4)
C120.022 (4)0.025 (5)0.044 (5)0.008 (4)0.000 (4)0.004 (4)
C130.033 (5)0.035 (5)0.039 (5)0.001 (4)0.002 (4)0.004 (4)
C140.043 (5)0.028 (5)0.042 (5)0.002 (4)0.003 (4)0.015 (4)
C150.041 (5)0.027 (5)0.040 (5)0.009 (4)0.000 (4)0.005 (4)
C160.034 (5)0.016 (4)0.048 (5)0.006 (4)0.004 (4)0.009 (4)
C170.033 (5)0.024 (4)0.038 (5)0.004 (4)0.002 (4)0.010 (4)
C180.041 (5)0.029 (5)0.042 (5)0.005 (4)0.005 (4)0.007 (4)
C190.034 (5)0.036 (6)0.052 (6)0.003 (4)0.002 (4)0.019 (5)
C200.027 (5)0.021 (5)0.056 (6)0.009 (4)0.006 (4)0.013 (4)
C210.030 (5)0.023 (5)0.049 (6)0.001 (4)0.002 (4)0.013 (4)
C220.036 (5)0.033 (5)0.044 (6)0.002 (4)0.005 (4)0.007 (4)
C230.038 (5)0.059 (6)0.047 (5)0.002 (5)0.001 (4)0.019 (5)
C240.030 (5)0.026 (5)0.050 (6)0.007 (4)0.002 (4)0.010 (4)
F250.051 (3)0.035 (3)0.049 (3)0.001 (3)0.003 (3)0.003 (3)
F260.034 (3)0.047 (4)0.048 (3)0.005 (3)0.009 (2)0.010 (3)
F270.054 (4)0.067 (5)0.039 (3)0.008 (3)0.010 (3)0.014 (3)
F280.078 (9)0.093 (9)0.070 (8)0.011 (8)0.012 (7)0.037 (8)
F290.048 (7)0.059 (7)0.083 (8)0.010 (6)0.021 (6)0.008 (6)
F300.048 (7)0.074 (8)0.067 (7)0.014 (6)0.008 (6)0.001 (6)
F28A0.062 (7)0.075 (8)0.055 (7)0.009 (7)0.017 (6)0.004 (7)
F29A0.088 (10)0.125 (11)0.106 (10)0.030 (9)0.002 (8)0.041 (9)
F30A0.075 (8)0.074 (9)0.097 (9)0.018 (7)0.031 (7)0.021 (7)
F310.044 (3)0.033 (3)0.053 (4)0.012 (3)0.004 (3)0.004 (3)
F320.039 (3)0.038 (3)0.045 (3)0.003 (3)0.009 (2)0.010 (3)
F330.038 (3)0.028 (3)0.044 (3)0.001 (2)0.004 (2)0.000 (2)
C340.029 (4)0.023 (4)0.029 (4)0.006 (4)0.003 (3)0.005 (3)
C350.034 (5)0.030 (5)0.033 (5)0.006 (4)0.005 (4)0.003 (4)
C360.033 (5)0.034 (6)0.042 (5)0.009 (4)0.006 (4)0.002 (4)
C370.050 (6)0.021 (5)0.046 (6)0.004 (5)0.012 (5)0.004 (4)
C380.050 (6)0.026 (5)0.043 (6)0.011 (5)0.004 (4)0.005 (4)
C390.046 (6)0.023 (5)0.034 (5)0.007 (4)0.004 (4)0.003 (4)
C400.027 (5)0.038 (6)0.045 (5)0.004 (4)0.005 (4)0.000 (4)
C410.063 (8)0.025 (6)0.074 (9)0.006 (6)0.020 (6)0.003 (5)
C420.044 (5)0.025 (5)0.041 (5)0.003 (4)0.001 (4)0.008 (4)
F430.041 (3)0.036 (3)0.054 (3)0.011 (3)0.009 (3)0.004 (3)
F440.032 (3)0.058 (4)0.054 (4)0.011 (3)0.002 (3)0.006 (3)
F450.046 (3)0.048 (4)0.050 (4)0.006 (3)0.014 (3)0.003 (3)
F460.061 (5)0.036 (4)0.237 (14)0.002 (4)0.065 (7)0.033 (6)
F470.093 (6)0.024 (3)0.096 (6)0.009 (4)0.023 (5)0.003 (3)
F480.167 (11)0.063 (6)0.106 (7)0.033 (7)0.023 (7)0.052 (6)
F490.046 (3)0.039 (3)0.054 (4)0.011 (3)0.009 (3)0.002 (3)
F500.045 (3)0.043 (3)0.054 (4)0.018 (3)0.002 (3)0.019 (3)
F510.025 (3)0.028 (3)0.061 (4)0.005 (2)0.002 (2)0.013 (3)
Sb10.0345 (4)0.0292 (4)0.0533 (4)0.0007 (3)0.0098 (3)0.0143 (3)
F10.076 (5)0.024 (3)0.068 (4)0.013 (3)0.024 (4)0.003 (3)
F20.040 (3)0.106 (7)0.063 (4)0.035 (4)0.001 (3)0.008 (4)
F30.079 (5)0.037 (4)0.123 (7)0.027 (4)0.048 (5)0.033 (4)
F40.048 (4)0.055 (4)0.120 (7)0.021 (4)0.034 (4)0.002 (4)
F50.044 (3)0.049 (4)0.044 (3)0.006 (3)0.004 (3)0.004 (3)
F60.088 (6)0.124 (8)0.046 (4)0.011 (5)0.014 (4)0.045 (5)
C520.082 (12)0.069 (11)0.090 (12)0.023 (9)0.008 (9)0.030 (9)
Cl10.186 (10)0.154 (9)0.173 (9)0.001 (8)0.025 (8)0.071 (8)
Cl20.272 (15)0.281 (16)0.277 (15)0.060 (10)0.038 (10)0.059 (10)
Geometric parameters (Å, º) top
Pd1—C12.052 (9)C22—F271.332 (12)
Pd1—N52.078 (8)C22—F251.348 (12)
Pd1—N92.187 (7)C23—F29A1.23 (3)
Pd1—P12.197 (2)C23—F30A1.28 (2)
P1—O61.591 (6)C23—F281.29 (2)
P1—C161.891 (9)C23—F301.30 (2)
P1—C341.894 (9)C23—F28A1.31 (2)
C1—H1A0.9800C23—F291.38 (2)
C1—H1B0.9800C24—F321.328 (12)
C1—H1C0.9800C24—F331.343 (11)
C3—N51.118 (13)C24—F311.358 (11)
C3—C41.448 (14)F28—F28A0.84 (2)
C4—H4A0.9800F28—F30A1.43 (3)
C4—H4B0.9800F29—F29A0.95 (3)
C4—H4C0.9800F29—F28A1.61 (3)
O6—C71.513 (10)F30—F30A1.08 (3)
C7—C101.519 (12)F30—F29A1.28 (3)
C7—C111.523 (13)C34—C351.410 (13)
C7—C81.533 (12)C34—C391.418 (14)
C8—N91.343 (12)C35—C361.374 (14)
C8—C151.381 (13)C35—C401.507 (15)
N9—C121.324 (12)C36—C371.375 (16)
C10—H10A0.9800C36—H360.9500
C10—H10B0.9800C37—C381.375 (16)
C10—H10C0.9800C37—C411.520 (14)
C11—H11A0.9800C38—C391.394 (14)
C11—H11B0.9800C38—H380.9500
C11—H11C0.9800C39—C421.498 (14)
C12—C131.392 (14)C40—F431.340 (12)
C12—H120.9500C40—F441.342 (12)
C13—C141.373 (15)C40—F451.351 (12)
C13—H130.9500C41—F461.292 (16)
C14—C151.392 (14)C41—F471.318 (14)
C14—H140.9500C41—F481.322 (19)
C15—H150.9500C42—F501.332 (12)
C16—C171.409 (14)C42—F511.338 (11)
C16—C211.430 (14)C42—F491.359 (12)
C17—C181.384 (14)Sb1—F61.865 (7)
C17—C221.507 (14)Sb1—F21.872 (7)
C18—C191.396 (15)Sb1—F11.873 (6)
C18—H180.9500Sb1—F31.880 (7)
C19—C201.367 (16)Sb1—F51.880 (6)
C19—C231.519 (14)Sb1—F41.887 (7)
C20—C211.367 (14)C52—Cl11.666 (18)
C20—H200.9500C52—Cl21.692 (18)
C21—C241.512 (15)C52—H52A0.9900
C22—F261.327 (12)C52—H52B0.9900
C1—Pd1—N588.1 (4)F28—C23—F28A37.6 (12)
C1—Pd1—N9176.6 (4)F30—C23—F28A131.5 (13)
N5—Pd1—N993.3 (3)F29A—C23—F2942.4 (15)
C1—Pd1—P191.8 (3)F30A—C23—F29138.1 (15)
N5—Pd1—P1174.1 (2)F28—C23—F29109.0 (16)
N9—Pd1—P187.0 (2)F30—C23—F29101.6 (15)
O6—P1—C1699.1 (4)F28A—C23—F2973.5 (15)
O6—P1—C3497.4 (4)F29A—C23—C19114.1 (14)
C16—P1—C34111.1 (4)F30A—C23—C19110.6 (13)
O6—P1—Pd1106.3 (3)F28—C23—C19112.6 (13)
C16—P1—Pd1123.4 (3)F30—C23—C19112.9 (12)
C34—P1—Pd1114.5 (3)F28A—C23—C19114.2 (12)
Pd1—C1—H1A109.5F29—C23—C19108.7 (11)
Pd1—C1—H1B109.5F32—C24—F33109.1 (8)
H1A—C1—H1B109.5F32—C24—F31106.8 (8)
Pd1—C1—H1C109.5F33—C24—F31104.3 (8)
H1A—C1—H1C109.5F32—C24—C21113.5 (9)
H1B—C1—H1C109.5F33—C24—C21112.8 (8)
N5—C3—C4178.6 (11)F31—C24—C21109.8 (8)
C3—C4—H4A109.5F28A—F28—C2373 (2)
C3—C4—H4B109.5F28A—F28—F30A124 (3)
H4A—C4—H4B109.5C23—F28—F30A55.9 (14)
C3—C4—H4C109.5F29A—F29—C2360.4 (19)
H4A—C4—H4C109.5F29A—F29—F28A104 (2)
H4B—C4—H4C109.5C23—F29—F28A51.4 (10)
C3—N5—Pd1172.5 (8)F30A—F30—F29A117 (2)
C7—O6—P1124.2 (5)F30A—F30—C2364.4 (15)
O6—C7—C10102.8 (7)F29A—F30—C2356.8 (14)
O6—C7—C11110.2 (7)F28—F28A—C2370 (2)
C10—C7—C11109.1 (8)F28—F28A—F29122 (3)
O6—C7—C8111.6 (7)C23—F28A—F2955.1 (12)
C10—C7—C8113.7 (8)F29—F29A—C2377 (2)
C11—C7—C8109.2 (8)F29—F29A—F30137 (3)
N9—C8—C15121.5 (9)C23—F29A—F3062.7 (16)
N9—C8—C7116.1 (8)F30—F30A—C2366.3 (17)
C15—C8—C7122.1 (9)F30—F30A—F28116 (2)
C12—N9—C8118.8 (8)C23—F30A—F2856.2 (12)
C12—N9—Pd1117.0 (6)C35—C34—C39115.7 (9)
C8—N9—Pd1121.8 (6)C35—C34—P1121.8 (7)
C7—C10—H10A109.5C39—C34—P1119.1 (7)
C7—C10—H10B109.5C36—C35—C34121.6 (10)
H10A—C10—H10B109.5C36—C35—C40110.1 (9)
C7—C10—H10C109.5C34—C35—C40128.3 (9)
H10A—C10—H10C109.5C35—C36—C37121.1 (10)
H10B—C10—H10C109.5C35—C36—H36119.4
C7—C11—H11A109.5C37—C36—H36119.4
C7—C11—H11B109.5C38—C37—C36119.2 (9)
H11A—C11—H11B109.5C38—C37—C41119.0 (11)
C7—C11—H11C109.5C36—C37—C41121.8 (11)
H11A—C11—H11C109.5C37—C38—C39120.4 (10)
H11B—C11—H11C109.5C37—C38—H38119.8
N9—C12—C13123.4 (9)C39—C38—H38119.8
N9—C12—H12118.3C38—C39—C34121.1 (10)
C13—C12—H12118.3C38—C39—C42111.1 (9)
C14—C13—C12117.7 (9)C34—C39—C42127.6 (8)
C14—C13—H13121.2F43—C40—F44105.3 (9)
C12—C13—H13121.2F43—C40—F45104.7 (8)
C13—C14—C15119.4 (9)F44—C40—F45106.7 (7)
C13—C14—H14120.3F43—C40—C35119.5 (8)
C15—C14—H14120.3F44—C40—C35111.8 (9)
C8—C15—C14119.1 (10)F45—C40—C35108.0 (8)
C8—C15—H15120.5F46—C41—F47109.7 (12)
C14—C15—H15120.5F46—C41—F48106.4 (12)
C17—C16—C21115.5 (9)F47—C41—F48104.6 (13)
C17—C16—P1124.5 (7)F46—C41—C37112.0 (12)
C21—C16—P1119.9 (7)F47—C41—C37111.6 (10)
C18—C17—C16122.2 (9)F48—C41—C37112.2 (12)
C18—C17—C22114.2 (9)F50—C42—F51106.5 (8)
C16—C17—C22123.5 (8)F50—C42—F49105.6 (8)
C17—C18—C19120.3 (10)F51—C42—F49105.2 (8)
C17—C18—H18119.9F50—C42—C39113.9 (8)
C19—C18—H18119.9F51—C42—C39115.3 (8)
C20—C19—C18118.1 (9)F49—C42—C39109.4 (8)
C20—C19—C23121.7 (10)F6—Sb1—F291.6 (4)
C18—C19—C23120.1 (10)F6—Sb1—F190.2 (4)
C21—C20—C19122.8 (9)F2—Sb1—F191.3 (4)
C21—C20—H20118.6F6—Sb1—F392.2 (4)
C19—C20—H20118.6F2—Sb1—F389.8 (4)
C20—C21—C16120.7 (10)F1—Sb1—F3177.4 (4)
C20—C21—C24114.2 (9)F6—Sb1—F5178.2 (3)
C16—C21—C24125.1 (9)F2—Sb1—F590.2 (3)
F26—C22—F27106.9 (8)F1—Sb1—F589.2 (3)
F26—C22—F25107.4 (8)F3—Sb1—F588.4 (3)
F27—C22—F25107.1 (8)F6—Sb1—F489.9 (4)
F26—C22—C17112.2 (8)F2—Sb1—F4178.2 (4)
F27—C22—C17111.1 (8)F1—Sb1—F489.8 (3)
F25—C22—C17111.9 (9)F3—Sb1—F489.0 (4)
F29A—C23—F30A106 (2)F5—Sb1—F488.3 (3)
F29A—C23—F28131.4 (17)Cl1—C52—Cl2105.5 (14)
F30A—C23—F2867.9 (16)Cl1—C52—H52A110.6
F29A—C23—F3060.5 (16)Cl2—C52—H52A110.6
F30A—C23—F3049.3 (13)Cl1—C52—H52B110.6
F28—C23—F30111.3 (16)Cl2—C52—H52B110.6
F29A—C23—F28A108.2 (19)H52A—C52—H52B108.8
F30A—C23—F28A102.4 (16)
C1—Pd1—P1—O6130.4 (4)F29A—C23—F29—F28A144 (2)
N5—Pd1—P1—O641 (2)F30A—C23—F29—F28A90 (3)
N9—Pd1—P1—O652.8 (3)F28—C23—F29—F28A12.6 (14)
C1—Pd1—P1—C1617.5 (5)F30—C23—F29—F28A130.1 (14)
N5—Pd1—P1—C1672 (2)C19—C23—F29—F28A110.5 (13)
N9—Pd1—P1—C16165.7 (4)F29A—C23—F30—F30A156 (2)
C1—Pd1—P1—C34123.3 (4)F28—C23—F30—F30A29.8 (19)
N5—Pd1—P1—C34147 (2)F28A—C23—F30—F30A67 (3)
N9—Pd1—P1—C3453.5 (4)F29—C23—F30—F30A145.7 (17)
C4—C3—N5—Pd112 (50)C19—C23—F30—F30A98.0 (17)
C1—Pd1—N5—C368 (6)F30A—C23—F30—F29A156 (2)
N9—Pd1—N5—C3115 (6)F28—C23—F30—F29A126 (2)
P1—Pd1—N5—C322 (8)F28A—C23—F30—F29A89 (3)
C16—P1—O6—C7161.2 (6)F29—C23—F30—F29A10.6 (16)
C34—P1—O6—C785.9 (7)C19—C23—F30—F29A105.7 (17)
Pd1—P1—O6—C732.4 (7)F30A—F28—F28A—C2325 (2)
P1—O6—C7—C10155.1 (6)C23—F28—F28A—F2919 (2)
P1—O6—C7—C1188.7 (8)F30A—F28—F28A—F296 (4)
P1—O6—C7—C832.9 (10)F29A—C23—F28A—F28136 (3)
O6—C7—C8—N970.3 (10)F30A—C23—F28A—F2823 (2)
C10—C7—C8—N9174.0 (8)F30—C23—F28A—F2869 (3)
C11—C7—C8—N951.8 (10)F29—C23—F28A—F28160 (2)
O6—C7—C8—C15116.6 (9)C19—C23—F28A—F2896 (2)
C10—C7—C8—C150.9 (13)F29A—C23—F28A—F2924.7 (16)
C11—C7—C8—C15121.2 (10)F30A—C23—F28A—F29136.9 (16)
C15—C8—N9—C123.8 (13)F28—C23—F28A—F29160 (2)
C7—C8—N9—C12169.4 (8)F30—C23—F28A—F2991 (2)
C15—C8—N9—Pd1158.1 (7)C19—C23—F28A—F29103.5 (13)
C7—C8—N9—Pd128.7 (10)F29A—F29—F28A—F2810 (3)
C1—Pd1—N9—C1264 (6)C23—F29—F28A—F2822 (2)
N5—Pd1—N9—C1252.0 (7)F29A—F29—F28A—C2331.9 (19)
P1—Pd1—N9—C12133.9 (7)F28A—F29—F29A—C2328.3 (15)
C1—Pd1—N9—C898 (6)C23—F29—F29A—F3020 (3)
N5—Pd1—N9—C8145.8 (7)F28A—F29—F29A—F308 (4)
P1—Pd1—N9—C828.3 (7)F30A—C23—F29A—F29146.0 (19)
C8—N9—C12—C133.9 (14)F28—C23—F29A—F2971 (3)
Pd1—N9—C12—C13158.9 (8)F30—C23—F29A—F29165 (2)
N9—C12—C13—C140.4 (15)F28A—C23—F29A—F2937 (2)
C12—C13—C14—C153.0 (15)C19—C23—F29A—F2992 (2)
N9—C8—C15—C140.4 (14)F30A—C23—F29A—F3018.6 (17)
C7—C8—C15—C14172.3 (9)F28—C23—F29A—F3093 (3)
C13—C14—C15—C83.1 (15)F28A—C23—F29A—F30128.0 (16)
O6—P1—C16—C17135.4 (8)F29—C23—F29A—F30165 (2)
C34—P1—C16—C1733.8 (9)C19—C23—F29A—F30103.7 (15)
Pd1—P1—C16—C17108.1 (8)F30A—F30—F29A—F292 (5)
O6—P1—C16—C2140.0 (8)C23—F30—F29A—F2923 (3)
C34—P1—C16—C21141.6 (7)F30A—F30—F29A—C2324 (2)
Pd1—P1—C16—C2176.5 (8)F29A—F30—F30A—C2322.2 (19)
C21—C16—C17—C185.7 (14)F29A—F30—F30A—F285 (3)
P1—C16—C17—C18169.9 (8)C23—F30—F30A—F2827.4 (15)
C21—C16—C17—C22177.1 (9)F29A—C23—F30A—F3021 (2)
P1—C16—C17—C227.3 (14)F28—C23—F30A—F30150.0 (19)
C16—C17—C18—C191.2 (16)F28A—C23—F30A—F30134.9 (17)
C22—C17—C18—C19178.5 (9)F29—C23—F30A—F3056 (3)
C17—C18—C19—C203.7 (15)C19—C23—F30A—F30103.0 (16)
C17—C18—C19—C23177.1 (10)F29A—C23—F30A—F28128.6 (19)
C18—C19—C20—C213.7 (16)F30—C23—F30A—F28150.0 (19)
C23—C19—C20—C21177.1 (10)F28A—C23—F30A—F2815.1 (16)
C19—C20—C21—C161.2 (16)F29—C23—F30A—F2894 (3)
C19—C20—C21—C24177.7 (10)C19—C23—F30A—F28106.9 (15)
C17—C16—C21—C205.7 (14)F28A—F28—F30A—F302 (4)
P1—C16—C21—C20170.1 (8)C23—F28—F30A—F3030.5 (17)
C17—C16—C21—C24173.0 (9)F28A—F28—F30A—C2329 (3)
P1—C16—C21—C2411.2 (13)O6—P1—C34—C35127.6 (8)
C18—C17—C22—F26148.1 (9)C16—P1—C34—C35129.6 (8)
C16—C17—C22—F2634.6 (13)Pd1—P1—C34—C3515.9 (8)
C18—C17—C22—F2728.5 (13)O6—P1—C34—C3930.7 (7)
C16—C17—C22—F27154.2 (9)C16—P1—C34—C3972.0 (8)
C18—C17—C22—F2591.1 (10)Pd1—P1—C34—C39142.4 (6)
C16—C17—C22—F2586.2 (11)C39—C34—C35—C369.2 (13)
C20—C19—C23—F29A57 (2)P1—C34—C35—C36149.8 (8)
C18—C19—C23—F29A124 (2)C39—C34—C35—C40167.8 (9)
C20—C19—C23—F30A63.4 (19)P1—C34—C35—C4033.1 (13)
C18—C19—C23—F30A115.8 (17)C34—C35—C36—C371.8 (15)
C20—C19—C23—F28137.2 (16)C40—C35—C36—C37175.7 (9)
C18—C19—C23—F2842 (2)C35—C36—C37—C385.7 (16)
C20—C19—C23—F3010 (2)C35—C36—C37—C41175.7 (10)
C18—C19—C23—F30169.1 (15)C36—C37—C38—C395.2 (16)
C20—C19—C23—F28A178.3 (15)C41—C37—C38—C39176.2 (10)
C18—C19—C23—F28A1 (2)C37—C38—C39—C342.7 (15)
C20—C19—C23—F29101.9 (15)C37—C38—C39—C42172.7 (9)
C18—C19—C23—F2978.9 (15)C35—C34—C39—C389.6 (13)
C20—C21—C24—F3290.2 (10)P1—C34—C39—C38150.0 (8)
C16—C21—C24—F3291.0 (11)C35—C34—C39—C42164.9 (9)
C20—C21—C24—F33145.1 (9)P1—C34—C39—C4235.4 (13)
C16—C21—C24—F3333.7 (13)C36—C35—C40—F43177.0 (9)
C20—C21—C24—F3129.2 (12)C34—C35—C40—F435.7 (15)
C16—C21—C24—F31149.6 (9)C36—C35—C40—F4453.4 (11)
F29A—C23—F28—F28A62 (3)C34—C35—C40—F44129.3 (10)
F30A—C23—F28—F28A155 (3)C36—C35—C40—F4563.7 (10)
F30—C23—F28—F28A131 (2)C34—C35—C40—F45113.6 (10)
F29—C23—F28—F28A20 (2)C38—C37—C41—F46167.1 (13)
C19—C23—F28—F28A101 (2)C36—C37—C41—F4614.3 (18)
F29A—C23—F28—F30A93 (3)C38—C37—C41—F4769.5 (17)
F30—C23—F28—F30A24.0 (16)C36—C37—C41—F47109.1 (14)
F28A—C23—F28—F30A155 (3)C38—C37—C41—F4847.5 (15)
F29—C23—F28—F30A135.3 (16)C36—C37—C41—F48133.9 (13)
C19—C23—F28—F30A104.0 (16)C38—C39—C42—F5062.7 (11)
F30A—C23—F29—F29A54 (3)C34—C39—C42—F50122.4 (10)
F28—C23—F29—F29A131 (2)C38—C39—C42—F51173.7 (9)
F30—C23—F29—F29A14 (2)C34—C39—C42—F511.3 (15)
F28A—C23—F29—F29A144 (2)C38—C39—C42—F4955.3 (11)
C19—C23—F29—F29A106 (2)C34—C39—C42—F49119.7 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···F1i0.982.403.365 (13)166
C12—H12···F5i0.952.603.276 (11)129
C4—H4A···F40.982.533.464 (13)158
C4—H4C···F2ii0.982.303.225 (13)155
C11—H11C···F5iii0.982.493.352 (11)146
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Pd(CH3)(C26H14F18NOP)(C2H3N)][SbF6]·0.5CH2Cl2
Mr1170.05
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)8.8635 (8), 12.1336 (12), 19.107 (2)
α, β, γ (°)79.166 (8), 80.147 (8), 78.266 (8)
V3)1957.2 (3)
Z2
Radiation typeCu Kα
µ (mm1)11.56
Crystal size (mm)0.15 × 0.10 × 0.05
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionNumerical
(SADABS; Bruker, 2007)
Tmin, Tmax0.276, 0.596
No. of measured, independent and
observed [I > 2σ(I)] reflections
12653, 6232, 4802
Rint0.052
(sin θ/λ)max1)0.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.191, 1.02
No. of reflections6232
No. of parameters590
No. of restraints63
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.1096P)2 + 11.4198P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)2.34, 0.95

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···F1i0.982.403.365 (13)166
C12—H12···F5i0.952.603.276 (11)129
C4—H4A···F40.982.533.464 (13)158
C4—H4C···F2ii0.982.303.225 (13)155
C11—H11C···F5iii0.982.493.352 (11)146
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x, y+1, z.
 

Acknowledgements

We thank Professor Maurice S. Brookhart for helpful discussions.

References

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