{Bis[2-(diphenyl­phosphino)eth­yl]phenyl­phosphine-κ3P,P′,P′′}chloridopalladium(II) hexa­fluoridophosphate

Vorce, P.R.; Miller, S.M.; Helm, M.L.

doi:10.1107/S1600536809022417

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m792

doi:10.1107/S1600536809022417

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{Bis[2-(diphenylphosphino)ethyl]phenylphosphine-κ³P,P′,P′′}chloridopalladium(II) hexafluoridophosphate

Paul R. Vorce,^a Susie M. Miller ^b and Monte L. Helm ^a ^*

^aChemistry Department, Fort Lewis College, 1000 Rim Drive, Durango, CO 81301, USA, and ^bChemistry Department, Colorado State University, Fort Collins, CO 80523, USA
^*Correspondence e-mail: helm_m@fortlewis.edu

(Received 28 May 2009; accepted 11 June 2009; online 20 June 2009)

In the title compound, [PdCl(C₃₄H₃₃P₃)]PF₆, the Pd^II atom adopts a distorted PdP₃Cl square-planar geometry arising from the P,P′,P′′-tridentate triphos ligand and a chloride ion.

Related literature

For the synthesis, see: King et al. (1971 ). The corresponding complex with a Pt^II metal center is concurently published (Heston et al., 2009 ). The corresponding Pd^II complex has been previously reported as a trifluoromethanesulfonate salt (Müller et al., 2000 ). The corresponding complexes with both Pt^II and Pd^II have been previously reported as chloride and diphenyltetrachloridostannate(IV) salts (Sevillano et al., 1999a ; Garcia-Seijo et al., 2001 ; Housecroft et al., 1990 ). For other group 10–triphos complexes, see: Sevillano et al. (1999b ); Fernadez et al. (2005); Aizawa et al. (2002 ); Bertinsson et al. (1983 ); Autissier et al. (2005 ); Fernandez et al. (2005 ).

Experimental

Crystal data

[PdCl(C₃₄H₃₃P₃)]PF₆
M_r = 821.33
Triclinic, $[P \overline 1]$
a = 11.2465 (5) Å
b = 11.8182 (5) Å
c = 15.5093 (7) Å
α = 69.029 (2)°
β = 70.439 (2)°
γ = 69.697 (2)°
V = 1752.27 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.84 mm⁻¹
T = 100 K
0.47 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.693, T_max = 0.917
48576 measured reflections
13341 independent reflections
10917 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.067
S = 1.03
13341 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Selected bond lengths (Å)

Pd1—P1	2.2176 (4)
Pd1—P2	2.3178 (4)
Pd1—P3	2.3329 (4)
Pd1—Cl1	2.3441 (4)

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022417/hb2992sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022417/hb2992Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title compound, (I), consists of a [Pd(triphos)Cl]⁺ cation and PF₆^- anion (Fig. 1). The cation shows a distorted square planar geometry around the metal center and the charge is balanced by a non-coordinating PF₆^- anion.

Related literature top

For the synthesis, see: King et al. (1971). The corresponding complex with a Pt(II) metal center is concurently published (Heston et al., 2009). The corresponding Pd^II complex has been previously reported as a trifluoromethanesulfonate salt (Muller et al., 2000). The corresponding complexes with both Pt(II) and Pd^II have been previously reported as chloride and diphenyltetrachlorostannate(IV) salts (Sevillano et al., 1999a; Garcia-Seijo et al., 2001; Housecroft et al., 1990). For other group 10–triphos complexes, see: Sevillano et al. (1999b); Fernadez et al. (2005); Aizawa et al. (2002); Bertinsson et al. (1983); Autissier et al. (2005). For related literature, see: Fernandez et al. (2005).

Experimental top

The title compound was prepared by a previously reported proceedure (King, et al., 1971). Colourless rods of (I) were grown by slow solvent evaporation of a saturated dichloromethane solution.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006; 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

	Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids.
	Fig. 2. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.

{Bis[2-(diphenylphosphino)ethyl]phenylphosphine-κ³P,P',P''}chloridopalladium(II) hexafluoridophosphate top

Crystal data top

[PdCl(C₃₄H₃₃P₃)]PF₆	Z = 2
M_r = 821.33	F(000) = 828
Triclinic, P1	D_x = 1.557 Mg m⁻³
Hall symbol: -P 1	Melting point: not measured K
a = 11.2465 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8182 (5) Å	Cell parameters from 9890 reflections
c = 15.5093 (7) Å	θ = 2.7–33.3°
α = 69.029 (2)°	µ = 0.84 mm⁻¹
β = 70.439 (2)°	T = 100 K
γ = 69.697 (2)°	Rod, colourless
V = 1752.27 (13) Å³	0.47 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	13341 independent reflections
Radiation source: fine-focus sealed tube	10917 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 33.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→17
T_min = 0.693, T_max = 0.917	k = −18→18
48576 measured reflections	l = −23→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0249P)² + 0.7353P] where P = (F_o² + 2F_c²)/3
13341 reflections	(Δ/σ)_max = 0.002
415 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[PdCl(C₃₄H₃₃P₃)]PF₆	γ = 69.697 (2)°
M_r = 821.33	V = 1752.27 (13) Å³
Triclinic, P1	Z = 2
a = 11.2465 (5) Å	Mo Kα radiation
b = 11.8182 (5) Å	µ = 0.84 mm⁻¹
c = 15.5093 (7) Å	T = 100 K
α = 69.029 (2)°	0.47 × 0.15 × 0.10 mm
β = 70.439 (2)°

Data collection top

Bruker APEXII CCD diffractometer	13341 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	10917 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.917	R_int = 0.030
48576 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.03	Δρ_max = 0.71 e Å⁻³
13341 reflections	Δρ_min = −0.67 e Å⁻³
415 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

	x	y	z	U_iso*/U_eq
Pd1	0.543690 (10)	0.544468 (10)	0.728992 (7)	0.01221 (3)
Cl1	0.66556 (3)	0.69224 (3)	0.64082 (3)	0.01911 (7)
P1	0.41725 (3)	0.41349 (3)	0.80705 (3)	0.01332 (7)
P2	0.34703 (3)	0.69724 (3)	0.73350 (3)	0.01374 (7)
P3	0.71382 (3)	0.36524 (3)	0.75901 (3)	0.01384 (7)
C1	0.63963 (14)	0.23211 (14)	0.82230 (11)	0.0178 (3)
H1A	0.6334	0.1964	0.7756	0.021*
H1B	0.6956	0.1658	0.8631	0.021*
C2	0.50294 (14)	0.27458 (14)	0.88395 (11)	0.0177 (3)
H2A	0.5089	0.2948	0.9388	0.021*
H2B	0.4566	0.2077	0.9082	0.021*
C3	0.26481 (14)	0.49798 (14)	0.87132 (11)	0.0182 (3)
H3A	0.2009	0.4465	0.9003	0.022*
H3B	0.2800	0.5191	0.9224	0.022*
C4	0.21432 (13)	0.61759 (14)	0.79763 (11)	0.0184 (3)
H4A	0.1379	0.6736	0.8297	0.022*
H4B	0.1869	0.5962	0.7523	0.022*
C5	0.32177 (14)	0.80673 (14)	0.79914 (10)	0.0156 (3)
C6	0.19906 (14)	0.89177 (15)	0.81373 (11)	0.0197 (3)
H6A	0.1315	0.8893	0.7911	0.024*
C7	0.17601 (16)	0.97952 (16)	0.86117 (12)	0.0242 (3)
H7A	0.0925	1.0370	0.8713	0.029*
C8	0.27491 (17)	0.98361 (16)	0.89391 (12)	0.0261 (4)
H8A	0.2591	1.0444	0.9260	0.031*
C9	0.39634 (16)	0.89942 (17)	0.87998 (12)	0.0250 (3)
H9A	0.4634	0.9022	0.9029	0.030*
C10	0.42046 (15)	0.81067 (15)	0.83243 (11)	0.0207 (3)
H10A	0.5039	0.7531	0.8228	0.025*
C11	0.31785 (13)	0.79486 (14)	0.61900 (10)	0.0158 (3)
C12	0.35593 (15)	0.90719 (15)	0.57975 (11)	0.0193 (3)
H12A	0.3897	0.9338	0.6156	0.023*
C13	0.34469 (16)	0.97972 (16)	0.48887 (12)	0.0259 (4)
H13A	0.3710	1.0557	0.4625	0.031*
C14	0.29516 (17)	0.94151 (18)	0.43648 (12)	0.0305 (4)
H14A	0.2872	0.9913	0.3742	0.037*
C15	0.25735 (19)	0.8311 (2)	0.47485 (13)	0.0337 (4)
H15A	0.2228	0.8055	0.4389	0.040*
C16	0.26919 (17)	0.75693 (18)	0.56544 (13)	0.0271 (4)
H16A	0.2441	0.6803	0.5909	0.033*
C17	0.79995 (13)	0.37155 (14)	0.83702 (10)	0.0156 (3)
C18	0.81699 (16)	0.48626 (15)	0.82975 (12)	0.0222 (3)
H18A	0.7779	0.5608	0.7880	0.027*
C19	0.89105 (16)	0.49210 (16)	0.88346 (13)	0.0245 (3)
H19A	0.9026	0.5705	0.8781	0.029*
C20	0.94768 (14)	0.38410 (15)	0.94455 (11)	0.0200 (3)
H20A	0.9981	0.3883	0.9812	0.024*
C21	0.93115 (15)	0.26977 (16)	0.95254 (11)	0.0211 (3)
H21A	0.9708	0.1956	0.9943	0.025*
C22	0.85680 (15)	0.26298 (15)	0.89975 (11)	0.0201 (3)
H22A	0.8446	0.1845	0.9062	0.024*
C23	0.84173 (13)	0.31713 (15)	0.66107 (11)	0.0173 (3)
C24	0.85893 (17)	0.40133 (16)	0.57143 (12)	0.0253 (3)
H24A	0.8039	0.4843	0.5612	0.030*
C25	0.95762 (18)	0.36365 (18)	0.49618 (13)	0.0327 (4)
H25A	0.9700	0.4211	0.4347	0.039*
C26	1.03721 (16)	0.24272 (18)	0.51127 (14)	0.0304 (4)
H26A	1.1042	0.2173	0.4600	0.037*
C27	1.01997 (16)	0.15849 (18)	0.60052 (13)	0.0286 (4)
H27A	1.0747	0.0754	0.6102	0.034*
C28	0.92312 (15)	0.19491 (16)	0.67579 (12)	0.0231 (3)
H28A	0.9119	0.1372	0.7372	0.028*
C29	0.37076 (14)	0.36381 (14)	0.72824 (11)	0.0170 (3)
C30	0.43949 (16)	0.37635 (18)	0.63357 (12)	0.0264 (4)
H30A	0.5137	0.4095	0.6100	0.032*
C31	0.40025 (19)	0.3407 (2)	0.57341 (13)	0.0337 (4)
H31A	0.4483	0.3484	0.5091	0.040*
C32	0.29116 (19)	0.29404 (19)	0.60692 (13)	0.0313 (4)
H32A	0.2642	0.2702	0.5655	0.038*
C33	0.2214 (2)	0.2821 (2)	0.70068 (14)	0.0359 (5)
H33A	0.1459	0.2511	0.7233	0.043*
C34	0.26129 (17)	0.31525 (18)	0.76138 (12)	0.0289 (4)
H34A	0.2142	0.3050	0.8260	0.035*
P4	0.21871 (4)	0.13320 (4)	1.11479 (3)	0.01765 (8)
F1	0.14268 (9)	0.04474 (9)	1.10733 (7)	0.0233 (2)
F2	0.23404 (11)	0.04420 (10)	1.21717 (7)	0.0334 (2)
F3	0.35426 (8)	0.05090 (9)	1.06650 (7)	0.0241 (2)
F4	0.29314 (10)	0.22256 (10)	1.12031 (9)	0.0334 (3)
F5	0.20332 (10)	0.22185 (10)	1.01037 (8)	0.0341 (3)
F6	0.08134 (9)	0.21610 (10)	1.16043 (9)	0.0359 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.01063 (5)	0.00951 (5)	0.01375 (5)	−0.00185 (3)	−0.00232 (3)	−0.00135 (4)
Cl1	0.01759 (15)	0.01486 (17)	0.02136 (17)	−0.00688 (13)	−0.00301 (13)	0.00013 (13)
P1	0.01253 (15)	0.01079 (17)	0.01399 (16)	−0.00290 (13)	−0.00164 (12)	−0.00189 (13)
P2	0.01197 (15)	0.01054 (17)	0.01684 (17)	−0.00140 (12)	−0.00385 (13)	−0.00272 (13)
P3	0.01189 (15)	0.01076 (17)	0.01771 (17)	−0.00135 (13)	−0.00379 (13)	−0.00387 (14)
C1	0.0156 (6)	0.0118 (7)	0.0239 (7)	−0.0031 (5)	−0.0050 (5)	−0.0026 (6)
C2	0.0174 (6)	0.0135 (7)	0.0188 (7)	−0.0043 (5)	−0.0045 (5)	−0.0001 (5)
C3	0.0151 (6)	0.0159 (7)	0.0193 (7)	−0.0039 (5)	0.0005 (5)	−0.0044 (6)
C4	0.0133 (6)	0.0129 (7)	0.0255 (7)	−0.0031 (5)	−0.0019 (5)	−0.0041 (6)
C5	0.0170 (6)	0.0122 (7)	0.0156 (6)	−0.0024 (5)	−0.0044 (5)	−0.0025 (5)
C6	0.0180 (6)	0.0178 (7)	0.0232 (7)	−0.0020 (6)	−0.0060 (6)	−0.0072 (6)
C7	0.0242 (7)	0.0193 (8)	0.0272 (8)	−0.0009 (6)	−0.0040 (6)	−0.0107 (7)
C8	0.0322 (8)	0.0220 (8)	0.0270 (8)	−0.0052 (7)	−0.0079 (7)	−0.0112 (7)
C9	0.0268 (8)	0.0274 (9)	0.0263 (8)	−0.0076 (7)	−0.0105 (6)	−0.0092 (7)
C10	0.0198 (7)	0.0208 (8)	0.0218 (7)	−0.0023 (6)	−0.0081 (6)	−0.0059 (6)
C11	0.0137 (6)	0.0138 (7)	0.0189 (7)	−0.0003 (5)	−0.0066 (5)	−0.0040 (5)
C12	0.0211 (7)	0.0158 (7)	0.0201 (7)	−0.0033 (6)	−0.0065 (6)	−0.0038 (6)
C13	0.0264 (8)	0.0199 (8)	0.0229 (8)	−0.0027 (6)	−0.0062 (6)	0.0010 (6)
C14	0.0279 (8)	0.0363 (10)	0.0194 (8)	−0.0009 (7)	−0.0116 (7)	−0.0002 (7)
C15	0.0347 (9)	0.0471 (12)	0.0274 (9)	−0.0119 (9)	−0.0166 (8)	−0.0099 (9)
C16	0.0310 (8)	0.0294 (9)	0.0278 (9)	−0.0122 (7)	−0.0122 (7)	−0.0067 (7)
C17	0.0130 (6)	0.0133 (7)	0.0179 (7)	−0.0010 (5)	−0.0030 (5)	−0.0043 (5)
C18	0.0245 (7)	0.0138 (7)	0.0293 (8)	−0.0023 (6)	−0.0129 (6)	−0.0037 (6)
C19	0.0258 (8)	0.0186 (8)	0.0347 (9)	−0.0047 (6)	−0.0128 (7)	−0.0094 (7)
C20	0.0162 (6)	0.0237 (8)	0.0213 (7)	−0.0029 (6)	−0.0053 (5)	−0.0091 (6)
C21	0.0212 (7)	0.0205 (8)	0.0199 (7)	−0.0038 (6)	−0.0082 (6)	−0.0022 (6)
C22	0.0227 (7)	0.0145 (7)	0.0229 (7)	−0.0045 (6)	−0.0080 (6)	−0.0029 (6)
C23	0.0136 (6)	0.0197 (7)	0.0224 (7)	−0.0052 (5)	−0.0033 (5)	−0.0100 (6)
C24	0.0296 (8)	0.0197 (8)	0.0252 (8)	−0.0102 (7)	0.0011 (6)	−0.0080 (7)
C25	0.0392 (10)	0.0307 (10)	0.0258 (9)	−0.0207 (8)	0.0096 (7)	−0.0098 (8)
C26	0.0206 (7)	0.0380 (11)	0.0365 (10)	−0.0127 (7)	0.0074 (7)	−0.0228 (8)
C27	0.0181 (7)	0.0313 (10)	0.0370 (10)	0.0007 (7)	−0.0048 (7)	−0.0188 (8)
C28	0.0186 (7)	0.0244 (8)	0.0251 (8)	0.0008 (6)	−0.0076 (6)	−0.0093 (7)
C29	0.0179 (6)	0.0135 (7)	0.0188 (7)	−0.0043 (5)	−0.0056 (5)	−0.0022 (5)
C30	0.0228 (7)	0.0368 (10)	0.0224 (8)	−0.0134 (7)	−0.0001 (6)	−0.0107 (7)
C31	0.0355 (9)	0.0511 (13)	0.0214 (8)	−0.0196 (9)	−0.0027 (7)	−0.0136 (8)
C32	0.0380 (10)	0.0370 (11)	0.0283 (9)	−0.0175 (8)	−0.0132 (7)	−0.0071 (8)
C33	0.0402 (10)	0.0468 (12)	0.0322 (10)	−0.0302 (9)	−0.0076 (8)	−0.0065 (9)
C34	0.0325 (9)	0.0381 (11)	0.0220 (8)	−0.0231 (8)	−0.0022 (7)	−0.0055 (7)
P4	0.01521 (16)	0.01243 (18)	0.0248 (2)	−0.00147 (14)	−0.00703 (14)	−0.00449 (15)
F1	0.0217 (4)	0.0182 (5)	0.0329 (5)	−0.0076 (4)	−0.0095 (4)	−0.0054 (4)
F2	0.0469 (6)	0.0305 (6)	0.0226 (5)	−0.0058 (5)	−0.0139 (5)	−0.0061 (4)
F3	0.0169 (4)	0.0213 (5)	0.0338 (5)	−0.0021 (4)	−0.0041 (4)	−0.0118 (4)
F4	0.0237 (5)	0.0232 (5)	0.0630 (8)	−0.0036 (4)	−0.0147 (5)	−0.0214 (5)
F5	0.0362 (6)	0.0240 (5)	0.0363 (6)	−0.0103 (5)	−0.0185 (5)	0.0098 (5)
F6	0.0185 (4)	0.0226 (5)	0.0633 (8)	0.0007 (4)	−0.0014 (5)	−0.0216 (5)

Geometric parameters (Å, º) top

Pd1—P1	2.2176 (4)	C15—C16	1.387 (3)
Pd1—P2	2.3178 (4)	C15—H15A	0.9500
Pd1—P3	2.3329 (4)	C16—H16A	0.9500
Pd1—Cl1	2.3441 (4)	C17—C18	1.394 (2)
P1—C29	1.8073 (16)	C17—C22	1.398 (2)
P1—C3	1.8193 (14)	C18—C19	1.392 (2)
P1—C2	1.8211 (15)	C18—H18A	0.9500
P2—C11	1.8037 (15)	C19—C20	1.381 (2)
P2—C5	1.8126 (15)	C19—H19A	0.9500
P2—C4	1.8476 (15)	C20—C21	1.384 (2)
P3—C23	1.8132 (15)	C20—H20A	0.9500
P3—C17	1.8185 (16)	C21—C22	1.389 (2)
P3—C1	1.8418 (15)	C21—H21A	0.9500
C1—C2	1.534 (2)	C22—H22A	0.9500
C1—H1A	0.9900	C23—C24	1.387 (2)
C1—H1B	0.9900	C23—C28	1.401 (2)
C2—H2A	0.9900	C24—C25	1.398 (2)
C2—H2B	0.9900	C24—H24A	0.9500
C3—C4	1.532 (2)	C25—C26	1.383 (3)
C3—H3A	0.9900	C25—H25A	0.9500
C3—H3B	0.9900	C26—C27	1.383 (3)
C4—H4A	0.9900	C26—H26A	0.9500
C4—H4B	0.9900	C27—C28	1.385 (2)
C5—C10	1.392 (2)	C27—H27A	0.9500
C5—C6	1.399 (2)	C28—H28A	0.9500
C6—C7	1.384 (2)	C29—C30	1.393 (2)
C6—H6A	0.9500	C29—C34	1.402 (2)
C7—C8	1.389 (2)	C30—C31	1.388 (3)
C7—H7A	0.9500	C30—H30A	0.9500
C8—C9	1.384 (2)	C31—C32	1.385 (3)
C8—H8A	0.9500	C31—H31A	0.9500
C9—C10	1.393 (2)	C32—C33	1.384 (3)
C9—H9A	0.9500	C32—H32A	0.9500
C10—H10A	0.9500	C33—C34	1.382 (3)
C11—C16	1.390 (2)	C33—H33A	0.9500
C11—C12	1.399 (2)	C34—H34A	0.9500
C12—C13	1.384 (2)	P4—F1	1.6158 (10)
C12—H12A	0.9500	P4—F2	1.5872 (11)
C13—C14	1.384 (3)	P4—F3	1.5997 (10)
C13—H13A	0.9500	P4—F4	1.5967 (11)
C14—C15	1.378 (3)	P4—F6	1.6005 (10)
C14—H14A	0.9500	P4—F5	1.6117 (11)

P1—Pd1—P2	83.905 (14)	C14—C15—H15A	120.1
P1—Pd1—P3	84.262 (14)	C16—C15—H15A	120.1
P2—Pd1—P3	166.221 (13)	C15—C16—C11	119.90 (17)
P1—Pd1—Cl1	175.897 (14)	C15—C16—H16A	120.1
P2—Pd1—Cl1	92.644 (14)	C11—C16—H16A	120.1
P3—Pd1—Cl1	99.430 (14)	C18—C17—C22	119.14 (15)
C29—P1—C3	105.15 (7)	C18—C17—P3	119.17 (12)
C29—P1—C2	108.28 (7)	C22—C17—P3	121.56 (12)
C3—P1—C2	113.38 (7)	C19—C18—C17	120.29 (15)
C29—P1—Pd1	112.53 (5)	C19—C18—H18A	120.1
C3—P1—Pd1	107.87 (5)	C17—C18—H18A	120.1
C2—P1—Pd1	109.64 (5)	C20—C19—C18	120.05 (15)
C11—P2—C5	104.67 (7)	C20—C19—H19A	120.1
C11—P2—C4	108.65 (7)	C18—C19—H19A	120.1
C5—P2—C4	104.60 (7)	C19—C20—C21	120.16 (15)
C11—P2—Pd1	115.24 (5)	C19—C20—H20A	120.1
C5—P2—Pd1	115.29 (5)	C21—C20—H20A	120.1
C4—P2—Pd1	107.76 (5)	C20—C21—C22	120.26 (15)
C23—P3—C17	104.71 (7)	C20—C21—H21A	120.1
C23—P3—C1	105.01 (7)	C22—C21—H21A	120.1
C17—P3—C1	106.71 (7)	C21—C22—C17	120.09 (15)
C23—P3—Pd1	120.12 (5)	C21—C22—H22A	120.1
C17—P3—Pd1	112.42 (5)	C17—C22—H22A	120.1
C1—P3—Pd1	106.97 (5)	C24—C23—C28	119.94 (14)
C1—C2—H2A	109.7	C24—C23—P3	119.98 (12)
P1—C2—H2A	111.0	C28—C23—P3	120.07 (12)
C1—C2—H2B	109.7	C23—C24—C25	119.72 (16)
P1—C2—H2B	111.0	C23—C24—H24A	120.1
C2—C1—P3	110.54 (10)	C25—C24—H24A	120.1
C2—C1—H1A	109.7	C26—C25—C24	119.95 (17)
P3—C1—H1A	109.7	C26—C25—H25A	120.1
C2—C1—H1B	109.7	C24—C25—H25A	120.1
P3—C1—H1B	109.7	C25—C26—C27	120.43 (15)
C1—C2—P1	106.09 (10)	C25—C26—H26A	120.1
C4—C3—P1	106.05 (10)	C27—C26—H26A	120.1
C4—C3—H3A	109.7	C26—C27—C28	120.18 (17)
P1—C3—H3A	111.0	C26—C27—H27A	120.1
C4—C3—H3B	109.7	C28—C27—H27A	120.1
P1—C3—H3B	111.0	C27—C28—C23	119.77 (16)
C3—C4—P2	108.46 (10)	C27—C28—H28A	120.1
C3—C4—H4A	109.7	C23—C28—H28A	120.1
P2—C4—H4A	111.0	C30—C29—C34	118.84 (15)
C3—C4—H4B	109.7	C30—C29—P1	121.20 (12)
P3—C4—H4B	103.0	C34—C29—P1	119.94 (12)
C10—C5—C6	119.82 (14)	C31—C30—C29	120.39 (15)
C10—C5—P2	122.34 (11)	C31—C30—H30A	120.1
C6—C5—P2	117.82 (12)	C29—C30—H30A	120.1
C7—C6—C5	120.02 (15)	C32—C31—C30	120.12 (16)
C7—C6—H6A	120.1	C32—C31—H31A	120.1
C5—C6—H6A	120.1	C30—C31—H31A	120.1
C6—C7—C8	120.02 (15)	C33—C32—C31	120.01 (17)
C6—C7—H7A	120.1	C33—C32—H32A	120.1
C8—C7—H7A	120.1	C31—C32—H32A	120.1
C9—C8—C7	120.21 (16)	C34—C33—C32	120.17 (16)
C9—C8—H8A	120.1	C34—C33—H33A	120.1
C7—C8—H8A	120.1	C32—C33—H33A	120.1
C8—C9—C10	120.21 (16)	C33—C34—C29	120.46 (16)
C8—C9—H9A	120.1	C33—C34—H34A	120.1
C10—C9—H9A	120.1	C29—C34—H34A	120.1
C5—C10—C9	119.72 (15)	F2—P4—F4	91.25 (6)
C5—C10—H10A	120.1	F2—P4—F3	90.49 (6)
C9—C10—H10A	120.1	F4—P4—F3	90.41 (5)
C16—C11—C12	119.14 (14)	F2—P4—F6	90.92 (6)
C16—C11—P2	121.99 (12)	F4—P4—F6	90.63 (6)
C12—C11—P2	118.63 (12)	F3—P4—F6	178.24 (6)
C13—C12—C11	120.33 (15)	F2—P4—F5	179.18 (6)
C13—C12—H12A	120.1	F4—P4—F5	89.44 (6)
C11—C12—H12A	120.1	F3—P4—F5	89.06 (6)
C14—C13—C12	120.02 (16)	F6—P4—F5	89.53 (6)
C14—C13—H13A	120.1	F2—P4—F1	89.86 (6)
C12—C13—H13A	120.1	F4—P4—F1	178.88 (6)
C15—C14—C13	119.87 (16)	F3—P4—F1	89.74 (5)
C15—C14—H14A	120.1	F6—P4—F1	89.19 (5)
C13—C14—H14A	120.1	F5—P4—F1	89.45 (6)
C14—C15—C16	120.72 (17)

Experimental details

Crystal data
Chemical formula	[PdCl(C₃₄H₃₃P₃)]PF₆
M_r	821.33
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	11.2465 (5), 11.8182 (5), 15.5093 (7)
α, β, γ (°)	69.029 (2), 70.439 (2), 69.697 (2)
V (Å³)	1752.27 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.47 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.693, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	48576, 13341, 10917
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.773

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.067, 1.03
No. of reflections	13341
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.67

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SAINT (Bruker, 2006, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Pd1—P1	2.2176 (4)	Pd1—P3	2.3329 (4)
Pd1—P2	2.3178 (4)	Pd1—Cl1	2.3441 (4)

Acknowledgements

We thank Research Corporation Cottrell Science Award (No. 7293) for funding supporting this study.

References

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