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-({bis­[2,4,6-tris­­(tri­fluorido­meth­yl)phen­yl]phosphan­yl­oxy}meth­yl)pyridine]­meth­ylpalladium(II) hexa­fluoro­anti­monate 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 27 January 2011; accepted 16 February 2011; online 23 February 2011)

In the title compound, [Pd(CH3)(C24H10F18NOP)(CH3CN)][SbF6]·0.5CH2Cl2, the PdII atom has a distorted square-planar environment being coordinated by an acetonitrile N atom [Pd—N = 2.079 (3) Å], a methyl C atom [Pd—C = 2.047 (4) Å] and the bidentate ligand 2-({[2,4,6-tris­(trifluoro­meth­yl)phen­yl]phosphan­yloxy}meth­yl)pyridine (L). In L, the short distance of 3.621 (3) Å between the centroids of pyridine and benzene rings indicates the presence of a ππ inter­action. The crystal packing exhibits weak inter­molecular C—H⋯F contacts. The solvent mol­ecule has been treated as disordered between two positions of equal occupancy related by an inversion center.

Related literature

For related compounds, see: Li et al. (2011[Li, L., White, P. S. & Hao, A. (2011). Acta Cryst. E67, m365.]) and references therein. Di[tris­(trifluoro­meth­yl)phen­yl]phosphine chloride was prepared according to 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.]).

[Scheme 1]

Experimental

Crystal data
  • [Pd(CH3)(C24H10F18NOP)(C2H3N)][SbF6]·0.5CH2Cl2

  • Mr = 1142.00

  • Triclinic, [P \overline 1]

  • a = 8.6993 (4) Å

  • b = 11.8120 (5) Å

  • c = 18.1494 (8) Å

  • α = 78.557 (2)°

  • β = 82.007 (2)°

  • γ = 79.526 (2)°

  • V = 1787.14 (14) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 12.64 mm−1

  • T = 100 K

  • 0.38 × 0.13 × 0.11 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 = 0.086, Tmax = 0.348

  • 19130 measured reflections

  • 6422 independent reflections

  • 5830 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.093

  • S = 1.05

  • 6422 reflections

  • 534 parameters

  • 3 restraints

  • H-atom parameters constrained

  • Δρmax = 1.46 e Å−3

  • Δρmin = −0.88 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4C⋯F16i 0.98 2.44 3.310 (10) 148
C11—H11B⋯F11 0.99 2.58 3.489 (9) 154
C9—H9⋯F11 0.95 2.47 3.345 (9) 152
Symmetry code: (i) x+1, 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

In continuation of our structural study of Pd complexes with phosphine-imine ligands (Li et al., 2011), we present here the title compound (I). In (I) (Fig. 1), each Pd center has a distorted square-planar environment being coordinated by acetonitrile [Pd—N 2.079 (3) Å], methyl [Pd—C 2.047 (4) Å] and bidentate ligand L. 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 related compounds, see: Li et al. (2011) and references therein. Di[tris(trifluoromethyl)phenyl]phosphine chloride was prepared according to Batsanov et al. (2002).

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. Di[tris(trifluoromethyl)phenyl]phosphine chloride were prepared according to the literature procedures(Batsanov et al., 2002). A flame-dried Schlenk flask was charged with purified 2-pyridyl-carbinal (138 mg, 1.27 mmol) and dried THF (5 ml). The solution was cooled to -78°C and stirred for 30 min, 1.6 mol/l n-BuLi in hexane (0.8 ml, 1.28 mmol) was added slowly. After stirring of 1.0 hrs at -78°C, 800 mg of di[tris(trifluoromethyl)phenyl]phosphine chloride in THF(2 ml) was added slowly. Stirring for 1 day at -78°C, and brought it to room temperature and stirred overnight. 3.0 ml degassed saturated NaCl solution was charged for hydrolysis. After separation, dry and column purification, the ligand of 2- methoxy(di(2,4,6-tris(trifluoromethyl) phenyl)phosphino)] pyridine(0.45 g) was obtained. The yield is 50%. The neutral complex was prepared by reaction of the above ligand (1.0 equiv.) and (COD)PdMeCl (1.0 equiv.) at RT, and the cationic complex was obtained by reacting the neutral complex(1.0 equiv) with AgSbF6 (1.0 equiv.) at RT. Single crystal of the cationic complex was cultivated by recrystallization of CH2Cl2 and pentane. Anal. Calcd for C27H16F24N2OPPdSb: C, 29.49; H, 1.47; N, 2.55. Found: C, 29.52; H, 1.30; N, 2.27.

Refinement top

C-bound 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. The H atoms and solvent molecules are omitted for clarity
Acetonitrile[2-({bis[2,4,6- tris(trifluoromethyl)phenyl]phosphanyloxy}methyl)pyridine]methylpalladium(II) hexafluoridoantimonate dichloromethane hemisolvate top
Crystal data top
[Pd(CH3)(C24H10F18NOP)(C2H3N)][SbF6]·0.5CH2Cl2Z = 2
Mr = 1142.00F(000) = 1098
Triclinic, P1Dx = 2.122 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 8.6993 (4) ÅCell parameters from 8055 reflections
b = 11.8120 (5) Åθ = 2.5–69.1°
c = 18.1494 (8) ŵ = 12.64 mm1
α = 78.557 (2)°T = 100 K
β = 82.007 (2)°Block, colourless
γ = 79.526 (2)°0.38 × 0.13 × 0.11 mm
V = 1787.14 (14) Å3
Data collection top
Bruker APEXII CCD
diffractometer
6422 independent reflections
Radiation source: fine-focus sealed tube5830 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ϕ and ω scansθmax = 69.7°, θmin = 2.5°
Absorption correction: numerical
(SAINT; Bruker, 2007)
h = 1010
Tmin = 0.086, Tmax = 0.348k = 1414
19130 measured reflectionsl = 2121
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0539P)2 + 2.2192P]
where P = (Fo2 + 2Fc2)/3
6422 reflections(Δ/σ)max = 0.043
534 parametersΔρmax = 1.46 e Å3
3 restraintsΔρmin = 0.88 e Å3
Crystal data top
[Pd(CH3)(C24H10F18NOP)(C2H3N)][SbF6]·0.5CH2Cl2γ = 79.526 (2)°
Mr = 1142.00V = 1787.14 (14) Å3
Triclinic, P1Z = 2
a = 8.6993 (4) ÅCu Kα radiation
b = 11.8120 (5) ŵ = 12.64 mm1
c = 18.1494 (8) ÅT = 100 K
α = 78.557 (2)°0.38 × 0.13 × 0.11 mm
β = 82.007 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
6422 independent reflections
Absorption correction: numerical
(SAINT; Bruker, 2007)
5830 reflections with I > 2σ(I)
Tmin = 0.086, Tmax = 0.348Rint = 0.035
19130 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0363 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 1.05Δρmax = 1.46 e Å3
6422 reflectionsΔρmin = 0.88 e Å3
534 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*/UeqOcc. (<1)
Pd10.88403 (6)0.79572 (4)0.19133 (3)0.02224 (17)
P10.7299 (2)0.67699 (15)0.26210 (10)0.0200 (4)
C10.8178 (10)0.9157 (7)0.2617 (5)0.0305 (17)
H1A0.91040.94640.26970.046*
H1B0.76980.87810.31030.046*
H1C0.74150.98010.23870.046*
N21.0136 (8)0.9151 (6)0.1220 (4)0.0279 (14)
C31.0826 (9)0.9841 (7)0.0885 (4)0.0251 (15)
C41.1735 (10)1.0729 (7)0.0447 (5)0.0316 (17)
H4A1.10141.14150.02320.047*
H4B1.24231.04060.00390.047*
H4C1.23741.09600.07800.047*
N50.9618 (7)0.6603 (6)0.1231 (3)0.0251 (13)
C61.1173 (9)0.6238 (7)0.1095 (4)0.0283 (16)
H61.18770.67520.11220.034*
C71.1789 (10)0.5154 (8)0.0918 (4)0.0318 (17)
H71.28930.49310.08200.038*
C81.0768 (10)0.4392 (8)0.0886 (5)0.0322 (17)
H81.11610.36260.07880.039*
C90.9161 (10)0.4774 (7)0.0999 (4)0.0295 (16)
H90.84410.42780.09620.035*
C100.8615 (9)0.5875 (7)0.1165 (4)0.0253 (15)
C110.6888 (9)0.6356 (7)0.1274 (4)0.0266 (16)
H11A0.67040.71600.09800.032*
H11B0.62920.58720.10680.032*
O120.6279 (6)0.6381 (4)0.2067 (3)0.0228 (10)
C130.5605 (8)0.7290 (6)0.3291 (4)0.0207 (14)
C140.4259 (9)0.7999 (6)0.2991 (4)0.0225 (14)
C150.2888 (9)0.8282 (6)0.3458 (4)0.0255 (15)
H150.19990.87550.32430.031*
C160.2801 (9)0.7889 (7)0.4226 (4)0.0272 (16)
C170.4112 (9)0.7274 (6)0.4540 (4)0.0259 (15)
H170.40760.70500.50740.031*
C180.5494 (9)0.6975 (6)0.4090 (4)0.0243 (15)
C190.4112 (9)0.8531 (7)0.2163 (4)0.0259 (15)
F200.3435 (5)0.7874 (4)0.1823 (2)0.0305 (10)
F210.5456 (5)0.8716 (4)0.1750 (2)0.0297 (10)
F220.3187 (6)0.9577 (4)0.2110 (3)0.0355 (11)
C230.1304 (10)0.8149 (8)0.4732 (5)0.0348 (18)
F240.0112 (6)0.8704 (6)0.4348 (3)0.0530 (15)
F250.1458 (8)0.8773 (8)0.5225 (5)0.084 (3)
F260.0838 (7)0.7169 (6)0.5117 (4)0.0626 (18)
C270.6838 (10)0.6287 (7)0.4516 (4)0.0306 (17)
F280.6692 (6)0.6487 (5)0.5223 (3)0.0436 (13)
F290.6908 (6)0.5127 (4)0.4572 (3)0.0388 (11)
F300.8222 (5)0.6545 (4)0.4194 (3)0.0348 (10)
C310.8327 (8)0.5257 (6)0.2986 (4)0.0207 (14)
C320.7605 (9)0.4264 (7)0.2976 (4)0.0260 (15)
C330.8487 (10)0.3176 (7)0.2930 (5)0.0304 (17)
H330.79810.25400.29030.036*
C341.0100 (10)0.3012 (7)0.2922 (5)0.0338 (19)
C351.0823 (9)0.3903 (7)0.3014 (5)0.0318 (17)
H351.19210.37650.30540.038*
C360.9955 (9)0.5019 (7)0.3047 (4)0.0263 (15)
C370.5854 (9)0.4261 (7)0.3027 (4)0.0275 (16)
F380.4982 (5)0.5129 (4)0.3348 (2)0.0268 (9)
F390.5506 (6)0.3264 (4)0.3475 (3)0.0340 (10)
F400.5333 (5)0.4294 (4)0.2367 (3)0.0334 (10)
C411.1054 (12)0.1834 (8)0.2817 (6)0.047 (2)
F421.0618 (9)0.0980 (5)0.3320 (4)0.076 (2)
F431.0811 (9)0.1564 (6)0.2159 (4)0.074 (2)
F441.2567 (7)0.1820 (6)0.2777 (5)0.076 (2)
C451.1009 (9)0.5837 (7)0.3185 (5)0.0292 (16)
F461.1596 (5)0.5423 (4)0.3843 (3)0.0351 (11)
F471.2226 (5)0.5887 (5)0.2645 (3)0.0364 (11)
F481.0343 (5)0.6941 (4)0.3209 (3)0.0317 (10)
Sb10.60710 (6)0.23126 (4)0.07962 (3)0.02735 (18)
F110.5822 (6)0.3936 (4)0.0756 (3)0.0385 (11)
F120.6312 (8)0.2064 (5)0.1830 (3)0.0544 (15)
F130.6346 (8)0.0698 (5)0.0829 (4)0.0577 (17)
F140.5886 (7)0.2566 (6)0.0242 (3)0.0483 (14)
F150.8255 (6)0.2283 (5)0.0575 (3)0.0467 (13)
F160.3891 (6)0.2383 (5)0.0997 (4)0.0528 (15)
Cl10.5356 (9)0.0251 (5)0.4168 (5)0.153 (3)
C500.390 (4)0.059 (2)0.481 (2)0.106 (13)0.50
H50A0.29310.03230.47290.127*0.50
H50B0.36700.14480.47950.127*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0200 (3)0.0197 (3)0.0254 (3)0.0038 (2)0.0024 (2)0.0004 (2)
P10.0169 (8)0.0179 (8)0.0230 (8)0.0007 (6)0.0016 (6)0.0008 (7)
C10.035 (4)0.022 (4)0.035 (4)0.004 (3)0.006 (3)0.004 (3)
N20.025 (3)0.027 (3)0.030 (3)0.006 (3)0.003 (3)0.000 (3)
C30.023 (4)0.025 (4)0.027 (4)0.002 (3)0.004 (3)0.004 (3)
C40.033 (4)0.028 (4)0.033 (4)0.011 (3)0.000 (3)0.000 (3)
N50.025 (3)0.025 (3)0.023 (3)0.005 (3)0.001 (2)0.000 (3)
C60.024 (4)0.033 (4)0.026 (4)0.006 (3)0.003 (3)0.001 (3)
C70.023 (4)0.039 (5)0.029 (4)0.003 (3)0.005 (3)0.003 (3)
C80.034 (4)0.030 (4)0.030 (4)0.000 (3)0.002 (3)0.007 (3)
C90.030 (4)0.033 (4)0.026 (4)0.008 (3)0.003 (3)0.007 (3)
C100.026 (4)0.030 (4)0.020 (3)0.007 (3)0.002 (3)0.004 (3)
C110.024 (4)0.034 (4)0.021 (3)0.006 (3)0.002 (3)0.002 (3)
O120.018 (2)0.025 (3)0.024 (2)0.003 (2)0.0003 (19)0.004 (2)
C130.017 (3)0.016 (3)0.027 (3)0.001 (3)0.001 (3)0.003 (3)
C140.024 (4)0.015 (3)0.029 (4)0.003 (3)0.006 (3)0.003 (3)
C150.024 (4)0.019 (4)0.033 (4)0.000 (3)0.006 (3)0.005 (3)
C160.028 (4)0.020 (4)0.034 (4)0.004 (3)0.003 (3)0.010 (3)
C170.033 (4)0.019 (4)0.025 (3)0.003 (3)0.002 (3)0.003 (3)
C180.025 (4)0.020 (4)0.028 (4)0.003 (3)0.003 (3)0.004 (3)
C190.023 (4)0.024 (4)0.028 (4)0.001 (3)0.003 (3)0.003 (3)
F200.028 (2)0.036 (3)0.028 (2)0.0051 (19)0.0070 (18)0.0070 (19)
F210.025 (2)0.029 (2)0.030 (2)0.0036 (18)0.0027 (18)0.0046 (19)
F220.038 (3)0.028 (2)0.035 (2)0.011 (2)0.007 (2)0.002 (2)
C230.027 (4)0.039 (5)0.035 (4)0.003 (4)0.001 (3)0.008 (4)
F240.029 (3)0.067 (4)0.046 (3)0.014 (3)0.006 (2)0.001 (3)
F250.046 (4)0.136 (7)0.091 (5)0.017 (4)0.020 (4)0.085 (6)
F260.043 (3)0.057 (4)0.065 (4)0.003 (3)0.024 (3)0.012 (3)
C270.032 (4)0.028 (4)0.026 (4)0.005 (3)0.004 (3)0.000 (3)
F280.043 (3)0.057 (3)0.026 (2)0.013 (2)0.010 (2)0.008 (2)
F290.039 (3)0.028 (2)0.040 (3)0.006 (2)0.004 (2)0.006 (2)
F300.025 (2)0.043 (3)0.036 (2)0.002 (2)0.0054 (19)0.006 (2)
C310.018 (3)0.019 (3)0.021 (3)0.000 (3)0.002 (3)0.001 (3)
C320.022 (4)0.025 (4)0.027 (4)0.003 (3)0.005 (3)0.002 (3)
C330.030 (4)0.023 (4)0.034 (4)0.004 (3)0.010 (3)0.002 (3)
C340.027 (4)0.024 (4)0.042 (5)0.003 (3)0.011 (3)0.000 (4)
C350.020 (4)0.028 (4)0.039 (4)0.002 (3)0.004 (3)0.004 (3)
C360.023 (4)0.025 (4)0.027 (4)0.001 (3)0.001 (3)0.001 (3)
C370.026 (4)0.022 (4)0.034 (4)0.005 (3)0.004 (3)0.006 (3)
F380.019 (2)0.025 (2)0.035 (2)0.0022 (17)0.0041 (17)0.0083 (19)
F390.030 (2)0.025 (2)0.044 (3)0.0108 (19)0.010 (2)0.004 (2)
F400.031 (2)0.037 (3)0.035 (2)0.010 (2)0.0001 (19)0.012 (2)
C410.037 (5)0.028 (5)0.062 (6)0.007 (4)0.020 (4)0.005 (4)
F420.086 (5)0.026 (3)0.089 (5)0.013 (3)0.036 (4)0.006 (3)
F430.087 (5)0.050 (4)0.076 (5)0.019 (4)0.004 (4)0.028 (4)
F440.034 (3)0.043 (3)0.148 (8)0.012 (3)0.005 (4)0.033 (4)
C450.019 (4)0.031 (4)0.032 (4)0.002 (3)0.003 (3)0.005 (3)
F460.029 (2)0.040 (3)0.033 (2)0.002 (2)0.0103 (19)0.004 (2)
F470.023 (2)0.048 (3)0.037 (3)0.012 (2)0.0014 (19)0.002 (2)
F480.026 (2)0.025 (2)0.043 (3)0.0037 (18)0.0132 (19)0.002 (2)
Sb10.0290 (3)0.0234 (3)0.0279 (3)0.0051 (2)0.0026 (2)0.0033 (2)
F110.035 (3)0.024 (2)0.056 (3)0.004 (2)0.004 (2)0.005 (2)
F120.083 (4)0.045 (3)0.028 (3)0.007 (3)0.006 (3)0.004 (2)
F130.083 (5)0.024 (3)0.063 (4)0.013 (3)0.017 (3)0.013 (3)
F140.050 (3)0.068 (4)0.030 (3)0.013 (3)0.007 (2)0.010 (3)
F150.025 (3)0.049 (3)0.060 (3)0.001 (2)0.001 (2)0.004 (3)
F160.029 (3)0.055 (3)0.074 (4)0.018 (3)0.015 (3)0.018 (3)
Cl10.147 (5)0.104 (4)0.221 (8)0.059 (4)0.011 (5)0.035 (5)
C500.09 (2)0.044 (14)0.19 (4)0.035 (15)0.02 (2)0.05 (2)
Geometric parameters (Å, º) top
Pd1—C12.047 (8)C19—F211.327 (9)
Pd1—N22.079 (7)C19—F201.336 (9)
Pd1—N52.170 (6)C19—F221.340 (9)
Pd1—P12.2146 (18)C23—F251.301 (11)
P1—O121.609 (5)C23—F261.328 (11)
P1—C131.870 (7)C23—F241.328 (10)
P1—C311.883 (7)C27—F301.324 (10)
C1—H1A0.9800C27—F281.335 (9)
C1—H1B0.9800C27—F291.344 (10)
C1—H1C0.9800C31—C361.408 (11)
N2—C31.128 (10)C31—C321.432 (10)
C3—C41.467 (11)C32—C331.383 (11)
C4—H4A0.9800C32—C371.513 (11)
C4—H4B0.9800C33—C341.379 (12)
C4—H4C0.9800C33—H330.9500
N5—C61.347 (10)C34—C351.367 (12)
N5—C101.363 (10)C34—C411.517 (11)
C6—C71.377 (12)C35—C361.403 (11)
C6—H60.9500C35—H350.9500
C7—C81.388 (12)C36—C451.523 (11)
C7—H70.9500C37—F401.329 (9)
C8—C91.388 (12)C37—F381.341 (9)
C8—H80.9500C37—F391.349 (9)
C9—C101.378 (11)C41—F421.294 (11)
C9—H90.9500C41—F441.305 (12)
C10—C111.507 (11)C41—F431.347 (14)
C11—O121.467 (8)C45—F461.332 (9)
C11—H11A0.9900C45—F481.334 (9)
C11—H11B0.9900C45—F471.340 (9)
C13—C141.418 (10)Sb1—F131.868 (5)
C13—C181.418 (10)Sb1—F161.870 (5)
C14—C151.394 (11)Sb1—F141.873 (5)
C14—C191.523 (10)Sb1—F121.876 (5)
C15—C161.374 (11)Sb1—F111.879 (5)
C15—H150.9500Sb1—F111.879 (5)
C16—C171.367 (11)Sb1—F151.881 (5)
C16—C231.506 (11)Cl1—C501.65 (2)
C17—C181.388 (11)C50—H50A0.9900
C17—H170.9500C50—H50B0.9900
C18—C271.510 (11)
C1—Pd1—N287.5 (3)F25—C23—F24107.8 (8)
C1—Pd1—N5176.1 (3)F26—C23—F24105.3 (7)
N2—Pd1—N594.4 (2)F25—C23—C16112.5 (7)
C1—Pd1—P191.4 (2)F26—C23—C16111.1 (7)
N2—Pd1—P1175.69 (19)F24—C23—C16112.6 (7)
N5—Pd1—P186.99 (17)F30—C27—F28106.8 (7)
O12—P1—C1396.7 (3)F30—C27—F29107.1 (6)
O12—P1—C3196.4 (3)F28—C27—F29106.2 (7)
C13—P1—C31112.8 (3)F30—C27—C18112.7 (7)
O12—P1—Pd1107.5 (2)F28—C27—C18111.7 (6)
C13—P1—Pd1122.6 (2)F29—C27—C18112.0 (7)
C31—P1—Pd1115.0 (2)C36—C31—C32115.5 (7)
Pd1—C1—H1A109.5C36—C31—P1122.0 (6)
Pd1—C1—H1B109.5C32—C31—P1119.5 (6)
H1A—C1—H1B109.5C33—C32—C31121.6 (7)
Pd1—C1—H1C109.5C33—C32—C37112.9 (7)
H1A—C1—H1C109.5C31—C32—C37125.5 (7)
H1B—C1—H1C109.5C34—C33—C32120.3 (8)
C3—N2—Pd1175.1 (6)C34—C33—H33119.9
N2—C3—C4179.5 (9)C32—C33—H33119.9
C3—C4—H4A109.5C35—C34—C33120.0 (8)
C3—C4—H4B109.5C35—C34—C41120.6 (8)
H4A—C4—H4B109.5C33—C34—C41119.3 (8)
C3—C4—H4C109.5C34—C35—C36120.5 (8)
H4A—C4—H4C109.5C34—C35—H35119.8
H4B—C4—H4C109.5C36—C35—H35119.8
C6—N5—C10118.0 (7)C35—C36—C31121.4 (7)
C6—N5—Pd1118.4 (5)C35—C36—C45110.3 (7)
C10—N5—Pd1119.8 (5)C31—C36—C45128.2 (7)
N5—C6—C7123.0 (7)F40—C37—F38108.0 (6)
N5—C6—H6118.5F40—C37—F39106.2 (6)
C7—C6—H6118.5F38—C37—F39105.4 (6)
C6—C7—C8118.8 (7)F40—C37—C32114.0 (6)
C6—C7—H7120.6F38—C37—C32113.5 (6)
C8—C7—H7120.6F39—C37—C32109.1 (7)
C9—C8—C7118.6 (8)F42—C41—F44111.0 (9)
C9—C8—H8120.7F42—C41—F43103.6 (9)
C7—C8—H8120.7F44—C41—F43105.5 (8)
C10—C9—C8119.8 (7)F42—C41—C34112.8 (7)
C10—C9—H9120.1F44—C41—C34112.9 (8)
C8—C9—H9120.1F43—C41—C34110.3 (9)
N5—C10—C9121.5 (7)F46—C45—F48106.3 (7)
N5—C10—C11115.9 (7)F46—C45—F47107.4 (6)
C9—C10—C11122.5 (7)F48—C45—F47106.3 (6)
O12—C11—C10113.5 (6)F46—C45—C36109.5 (6)
O12—C11—H11A108.9F48—C45—C36116.7 (6)
C10—C11—H11A108.9F47—C45—C36110.2 (7)
O12—C11—H11B108.9F13—Sb1—F1691.2 (3)
C10—C11—H11B108.9F13—Sb1—F1490.0 (3)
H11A—C11—H11B107.7F16—Sb1—F1489.7 (3)
C11—O12—P1120.4 (4)F13—Sb1—F1290.2 (3)
C14—C13—C18115.7 (6)F16—Sb1—F1291.8 (3)
C14—C13—P1118.6 (5)F14—Sb1—F12178.5 (3)
C18—C13—P1125.5 (5)F13—Sb1—F11179.2 (3)
C15—C14—C13121.0 (7)F16—Sb1—F1189.6 (2)
C15—C14—C19112.6 (6)F14—Sb1—F1189.8 (3)
C13—C14—C19126.3 (7)F12—Sb1—F1190.0 (2)
C16—C15—C14121.0 (7)F13—Sb1—F11179.2 (3)
C16—C15—H15119.5F16—Sb1—F1189.6 (2)
C14—C15—H15119.5F14—Sb1—F1189.8 (3)
C17—C16—C15119.4 (7)F12—Sb1—F1190.0 (2)
C17—C16—C23119.1 (7)F11—Sb1—F110.0 (3)
C15—C16—C23121.5 (7)F13—Sb1—F1590.1 (3)
C16—C17—C18120.8 (7)F16—Sb1—F15178.4 (3)
C16—C17—H17119.6F14—Sb1—F1589.3 (3)
C18—C17—H17119.6F12—Sb1—F1589.2 (3)
C17—C18—C13121.7 (7)F11—Sb1—F1589.1 (2)
C17—C18—C27114.9 (7)F11—Sb1—F1589.1 (2)
C13—C18—C27123.4 (7)F11—F11—Sb10 (10)
F21—C19—F20107.6 (6)C50—Cl1—C50i74.4 (19)
F21—C19—F22105.9 (6)Cl1—C50—Cl1i105.6 (19)
F20—C19—F22106.3 (6)Cl1—C50—H50A110.6
F21—C19—C14114.9 (6)Cl1i—C50—H50A110.6
F20—C19—C14111.7 (6)Cl1—C50—H50B110.6
F22—C19—C14109.8 (6)Cl1i—C50—H50B110.6
F25—C23—F26107.0 (8)H50A—C50—H50B108.7
C1—Pd1—P1—O12130.9 (3)C15—C14—C19—F21153.5 (6)
N2—Pd1—P1—O1257 (3)C13—C14—C19—F2126.5 (10)
N5—Pd1—P1—O1252.7 (3)C15—C14—C19—F2083.6 (8)
C1—Pd1—P1—C1320.6 (4)C13—C14—C19—F2096.5 (8)
N2—Pd1—P1—C1354 (3)C15—C14—C19—F2234.2 (9)
N5—Pd1—P1—C13163.0 (3)C13—C14—C19—F22145.7 (7)
C1—Pd1—P1—C31123.1 (3)C17—C16—C23—F2560.7 (11)
N2—Pd1—P1—C31163 (3)C15—C16—C23—F25117.5 (9)
N5—Pd1—P1—C3153.3 (3)C17—C16—C23—F2659.3 (10)
C1—Pd1—N2—C315 (8)C15—C16—C23—F26122.5 (8)
N5—Pd1—N2—C3162 (8)C17—C16—C23—F24177.2 (7)
P1—Pd1—N2—C389 (8)C15—C16—C23—F244.6 (11)
Pd1—N2—C3—C4132 (100)C17—C18—C27—F30145.4 (7)
C1—Pd1—N5—C662 (4)C13—C18—C27—F3035.2 (10)
N2—Pd1—N5—C656.6 (6)C17—C18—C27—F2825.3 (10)
P1—Pd1—N5—C6127.5 (6)C13—C18—C27—F28155.4 (7)
C1—Pd1—N5—C1096 (4)C17—C18—C27—F2993.7 (8)
N2—Pd1—N5—C10145.5 (6)C13—C18—C27—F2985.6 (9)
P1—Pd1—N5—C1030.4 (5)O12—P1—C31—C36134.8 (6)
C10—N5—C6—C72.2 (11)C13—P1—C31—C36125.2 (6)
Pd1—N5—C6—C7156.1 (6)Pd1—P1—C31—C3622.1 (7)
N5—C6—C7—C80.7 (12)O12—P1—C31—C3225.0 (6)
C6—C7—C8—C92.9 (12)C13—P1—C31—C3275.1 (6)
C7—C8—C9—C102.1 (12)Pd1—P1—C31—C32137.7 (5)
C6—N5—C10—C93.0 (11)C36—C31—C32—C338.2 (11)
Pd1—N5—C10—C9155.0 (6)P1—C31—C32—C33152.8 (6)
C6—N5—C10—C11176.2 (6)C36—C31—C32—C37170.7 (7)
Pd1—N5—C10—C1125.8 (8)P1—C31—C32—C3728.2 (10)
C8—C9—C10—N50.8 (12)C31—C32—C33—C342.7 (12)
C8—C9—C10—C11178.3 (7)C37—C32—C33—C34176.4 (7)
N5—C10—C11—O1275.3 (8)C32—C33—C34—C354.6 (13)
C9—C10—C11—O12105.5 (8)C32—C33—C34—C41175.9 (8)
C10—C11—O12—P140.9 (8)C33—C34—C35—C365.8 (13)
C13—P1—O12—C11154.3 (5)C41—C34—C35—C36174.7 (8)
C31—P1—O12—C1191.7 (6)C34—C35—C36—C310.3 (12)
Pd1—P1—O12—C1127.0 (6)C34—C35—C36—C45177.6 (7)
O12—P1—C13—C1445.0 (6)C32—C31—C36—C357.0 (11)
C31—P1—C13—C14144.8 (5)P1—C31—C36—C35153.5 (6)
Pd1—P1—C13—C1470.7 (6)C32—C31—C36—C45170.4 (7)
O12—P1—C13—C18130.7 (6)P1—C31—C36—C4529.1 (11)
C31—P1—C13—C1830.9 (7)C33—C32—C37—F4079.3 (9)
Pd1—P1—C13—C18113.5 (6)C31—C32—C37—F40101.7 (9)
C18—C13—C14—C154.7 (10)C33—C32—C37—F38156.4 (7)
P1—C13—C14—C15171.4 (5)C31—C32—C37—F3822.6 (11)
C18—C13—C14—C19175.2 (7)C33—C32—C37—F3939.2 (9)
P1—C13—C14—C198.6 (9)C31—C32—C37—F39139.8 (7)
C13—C14—C15—C160.4 (11)C35—C34—C41—F42122.7 (11)
C19—C14—C15—C16179.5 (7)C33—C34—C41—F4256.8 (14)
C14—C15—C16—C174.3 (11)C35—C34—C41—F444.1 (14)
C14—C15—C16—C23177.5 (7)C33—C34—C41—F44176.3 (9)
C15—C16—C17—C184.5 (11)C35—C34—C41—F43121.9 (10)
C23—C16—C17—C18177.2 (7)C33—C34—C41—F4358.5 (11)
C16—C17—C18—C130.0 (11)C35—C36—C45—F4661.1 (8)
C16—C17—C18—C27179.4 (7)C31—C36—C45—F46116.6 (8)
C14—C13—C18—C174.5 (10)C35—C36—C45—F48178.2 (7)
P1—C13—C18—C17171.3 (6)C31—C36—C45—F484.2 (12)
C14—C13—C18—C27176.1 (7)C35—C36—C45—F4756.8 (8)
P1—C13—C18—C278.0 (10)C31—C36—C45—F47125.5 (8)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4C···F16ii0.982.443.310 (10)148
C11—H11B···F110.992.583.489 (9)154
C9—H9···F110.952.473.345 (9)152
Symmetry code: (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Pd(CH3)(C24H10F18NOP)(C2H3N)][SbF6]·0.5CH2Cl2
Mr1142.00
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)8.6993 (4), 11.8120 (5), 18.1494 (8)
α, β, γ (°)78.557 (2), 82.007 (2), 79.526 (2)
V3)1787.14 (14)
Z2
Radiation typeCu Kα
µ (mm1)12.64
Crystal size (mm)0.38 × 0.13 × 0.11
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionNumerical
(SAINT; Bruker, 2007)
Tmin, Tmax0.086, 0.348
No. of measured, independent and
observed [I > 2σ(I)] reflections
19130, 6422, 5830
Rint0.035
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.093, 1.05
No. of reflections6422
No. of parameters534
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.46, 0.88

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—H4C···F16i0.982.443.310 (10)148
C11—H11B···F110.992.583.489 (9)154
C9—H9···F110.952.473.345 (9)152
Symmetry code: (i) x+1, y+1, z.
 

Acknowledgements

We thank Professor Maurice S. Brookhart for helpful discussions.

References

First citationBatsanov, A., Cornet, S. M., Dillon, K. B., Goeta, A. E., Hazendonk, P. & Thompson, A. L. (2002). J. Chem. Soc. Dalton Trans. pp. 4622–4628.  Web of Science CSD CrossRef Google Scholar
First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, L., White, P. S. & Hao, A. (2011). Acta Cryst. E67, m365.  Web of Science CSD CrossRef IUCr Journals 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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