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

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

doi:10.1107/S160053681001319X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page m522

https://doi.org/10.1107/S160053681001319X

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

A. Ahmida Aziza,^a Ulrich Flörke,^a ^* Hans Egold ^a and Gerald Henkel ^a

^aDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, 33098 Paderborn, Germany
^*Correspondence e-mail: ulrich.floerke@upb.de

(Received 16 March 2010; accepted 9 April 2010; online 14 April 2010)

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 Pd^II atom, which lies 0.212 (1) Å above the coordination plane. The sum of the bond angles at Pd^II 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.

Related literature

For the structures of related Pd^II 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

Crystal data

[Pd(C₁₉H₂₁N₂P)₂](PF₆)₂·2.85C₂H₃N
M_r = 1130.45
Triclinic, $[P \overline 1]$
a = 11.114 (2) Å
b = 11.343 (2) Å
c = 20.243 (4) Å
α = 77.490 (4)°
β = 83.580 (5)°
γ = 85.301 (4)°
V = 2471.4 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 120 K
0.42 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.790, T_max = 0.891
20500 measured reflections
10802 independent reflections
9025 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.129
S = 1.05
10802 reflections
584 parameters
H-atom parameters constrained
Δρ_max = 0.90 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Pd1—C31	2.031 (3)
Pd1—C1	2.033 (3)
Pd1—P1	2.3085 (9)
Pd1—P2	2.3100 (9)

C31—Pd1—C1	173.56 (13)
C31—Pd1—P1	94.24 (9)
C1—Pd1—P1	84.03 (10)
C31—Pd1—P2	83.54 (9)
C1—Pd1—P2	96.46 (10)
P1—Pd1—P2	164.44 (3)

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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 I, global. DOI: https://doi.org/10.1107/S160053681001319X/wm2316sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001319X/wm2316Isup2.hkl

checkCIF report

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 Pd^II 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.

Structure description top

For the structures of related Pd^II 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).

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

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)₂·2.85C₂H₃N	Z = 2
M_r = 1130.45	F(000) = 1150
Triclinic, P1	D_x = 1.519 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.114 (2) Å	Cell parameters from 1002 reflections
b = 11.343 (2) Å	θ = 2.3–28.1°
c = 20.243 (4) Å	µ = 0.59 mm⁻¹
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 tube	9025 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 27.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→14
T_min = 0.790, T_max = 0.891	k = −14→14
20500 measured reflections	l = −24→25

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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0605P)² + 3.077P] where P = (F_o² + 2F_c²)/3
10802 reflections	(Δ/σ)_max < 0.001
584 parameters	Δρ_max = 0.90 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Pd(C₁₉H₂₁N₂P)₂](PF₆)₂·2.85C₂H₃N	γ = 85.301 (4)°
M_r = 1130.45	V = 2471.4 (8) Å³
Triclinic, P1	Z = 2
a = 11.114 (2) Å	Mo Kα radiation
b = 11.343 (2) Å	µ = 0.59 mm⁻¹
c = 20.243 (4) Å	T = 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)
T_min = 0.790, T_max = 0.891	R_int = 0.032
20500 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	Δρ_max = 0.90 e Å⁻³
10802 reflections	Δρ_min = −0.56 e Å⁻³
584 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pd1	0.14297 (2)	0.58147 (2)	0.214403 (12)	0.01778 (8)
P1	0.10291 (8)	0.69609 (8)	0.29654 (4)	0.02250 (19)
P2	0.14709 (8)	0.50588 (8)	0.11694 (4)	0.02037 (18)
N1	−0.0082 (3)	0.3656 (3)	0.29190 (14)	0.0242 (6)
N2	−0.1052 (3)	0.5386 (3)	0.28212 (14)	0.0233 (6)
N3	0.3767 (3)	0.7229 (2)	0.16884 (14)	0.0216 (6)
N4	0.2425 (2)	0.7651 (2)	0.09788 (14)	0.0215 (6)
C1	0.0041 (3)	0.4847 (3)	0.26744 (16)	0.0220 (7)
C2	0.0877 (4)	0.2695 (3)	0.28886 (19)	0.0318 (8)
H2A	0.1630	0.3058	0.2653	0.038*
H2B	0.0633	0.2136	0.2621	0.038*
C3	0.1126 (4)	0.1990 (4)	0.3589 (2)	0.0424 (10)
H3A	0.1764	0.1354	0.3547	0.064*
H3B	0.0384	0.1622	0.3822	0.064*
H3C	0.1390	0.2537	0.3851	0.064*
C4	−0.1260 (3)	0.3454 (3)	0.32047 (17)	0.0280 (8)
H4A	−0.1578	0.2692	0.3406	0.034*
C5	−0.1863 (3)	0.4538 (3)	0.31420 (17)	0.0256 (7)
H5A	−0.2691	0.4692	0.3290	0.031*
C6	−0.1331 (3)	0.6692 (3)	0.26246 (18)	0.0267 (7)
H6A	−0.2208	0.6868	0.2738	0.032*
H6B	−0.1152	0.6955	0.2126	0.032*
C7	−0.0607 (3)	0.7417 (3)	0.2980 (2)	0.0299 (8)
H7A	−0.0954	0.7329	0.3459	0.036*
H7B	−0.0703	0.8284	0.2759	0.036*
C11	0.1811 (3)	0.8350 (3)	0.2794 (2)	0.0301 (8)
C12	0.2725 (4)	0.8492 (4)	0.3179 (2)	0.0412 (10)
H12A	0.2886	0.7895	0.3572	0.049*
C13	0.3400 (5)	0.9504 (5)	0.2990 (3)	0.0581 (14)
H13A	0.4010	0.9612	0.3261	0.070*
C14	0.3197 (5)	1.0347 (4)	0.2416 (3)	0.0620 (16)
H14A	0.3678	1.1030	0.2285	0.074*
C15	0.2303 (4)	1.0217 (4)	0.2027 (3)	0.0551 (14)
H15A	0.2168	1.0810	0.1628	0.066*
C16	0.1588 (4)	0.9219 (3)	0.2213 (2)	0.0396 (10)
H16A	0.0960	0.9135	0.1948	0.047*
C21	0.1273 (3)	0.6228 (3)	0.38290 (17)	0.0273 (7)
C22	0.0872 (4)	0.6806 (4)	0.4361 (2)	0.0399 (10)
H22A	0.0465	0.7585	0.4270	0.048*
C23	0.1068 (5)	0.6240 (6)	0.5024 (2)	0.0529 (13)
H23A	0.0802	0.6635	0.5387	0.063*
C24	0.1641 (5)	0.5121 (5)	0.5151 (2)	0.0538 (13)
H24A	0.1756	0.4733	0.5606	0.065*
C25	0.2059 (5)	0.4536 (5)	0.4633 (2)	0.0493 (12)
H25A	0.2468	0.3758	0.4731	0.059*
C26	0.1879 (4)	0.5092 (4)	0.39648 (19)	0.0352 (9)
H26A	0.2167	0.4697	0.3604	0.042*
C31	0.2673 (3)	0.6927 (3)	0.15747 (16)	0.0200 (6)
C32	0.4479 (3)	0.6611 (3)	0.22448 (18)	0.0294 (8)
H32A	0.3963	0.6051	0.2581	0.035*
H32B	0.4742	0.7216	0.2477	0.035*
C33	0.5575 (3)	0.5912 (3)	0.1988 (2)	0.0334 (8)
H33A	0.6026	0.5504	0.2371	0.050*
H33B	0.6096	0.6468	0.1664	0.050*
H33C	0.5315	0.5308	0.1761	0.050*
C34	0.4190 (3)	0.8157 (3)	0.11711 (18)	0.0263 (7)
H34A	0.4934	0.8534	0.1139	0.032*
C35	0.3350 (3)	0.8424 (3)	0.07238 (18)	0.0257 (7)
H35A	0.3384	0.9023	0.0315	0.031*
C36	0.1317 (3)	0.7596 (3)	0.06651 (18)	0.0252 (7)
H36A	0.1286	0.8249	0.0253	0.030*
H36B	0.0605	0.7732	0.0986	0.030*
C37	0.1246 (4)	0.6381 (3)	0.04706 (17)	0.0281 (8)
H37A	0.1869	0.6319	0.0088	0.034*
H37B	0.0443	0.6354	0.0308	0.034*
C41	0.0274 (3)	0.4071 (3)	0.11525 (17)	0.0230 (7)
C42	−0.0919 (3)	0.4487 (3)	0.13059 (17)	0.0267 (7)
H42A	−0.1088	0.5300	0.1356	0.032*
C43	−0.1864 (3)	0.3721 (4)	0.13863 (19)	0.0322 (8)
H43A	−0.2674	0.4003	0.1499	0.039*
C44	−0.1616 (4)	0.2546 (4)	0.13016 (19)	0.0352 (9)
H44A	−0.2257	0.2016	0.1365	0.042*
C45	−0.0438 (4)	0.2132 (3)	0.1125 (2)	0.0353 (9)
H45A	−0.0276	0.1330	0.1056	0.042*
C46	0.0501 (4)	0.2903 (3)	0.10514 (19)	0.0287 (8)
H46A	0.1307	0.2624	0.0930	0.034*
C51	0.2878 (3)	0.4266 (3)	0.09389 (17)	0.0238 (7)
C52	0.3191 (4)	0.4080 (4)	0.0279 (2)	0.0356 (9)
H52A	0.2669	0.4395	−0.0067	0.043*
C53	0.4262 (4)	0.3436 (4)	0.0130 (2)	0.0443 (10)
H53A	0.4468	0.3311	−0.0319	0.053*
C54	0.5031 (4)	0.2975 (4)	0.0622 (2)	0.0396 (10)
H54A	0.5763	0.2534	0.0513	0.047*
C55	0.4740 (4)	0.3153 (3)	0.1277 (2)	0.0335 (8)
H55A	0.5274	0.2843	0.1617	0.040*
C56	0.3655 (3)	0.3792 (3)	0.14365 (18)	0.0262 (7)
H56A	0.3448	0.3903	0.1888	0.031*
P10	0.78890 (8)	0.89315 (8)	0.08279 (5)	0.0250 (2)
F11	0.7426 (2)	1.03165 (19)	0.07981 (13)	0.0408 (6)
F12	0.8351 (2)	0.7545 (2)	0.08694 (13)	0.0425 (6)
F13	0.6962 (2)	0.8529 (2)	0.14901 (11)	0.0391 (5)
F14	0.6869 (2)	0.8796 (2)	0.03586 (12)	0.0380 (5)
F15	0.8896 (2)	0.9069 (2)	0.13115 (12)	0.0383 (5)
F16	0.8808 (2)	0.9332 (2)	0.01755 (12)	0.0446 (6)
P20	0.49733 (11)	0.28058 (11)	0.35088 (6)	0.0413 (3)
F21	0.5132 (3)	0.4160 (3)	0.35538 (17)	0.0684 (9)
F22	0.6133 (3)	0.2418 (3)	0.38990 (17)	0.0776 (10)
F23	0.5813 (3)	0.3003 (3)	0.28115 (14)	0.0584 (7)
F24	0.3828 (3)	0.3256 (5)	0.31074 (19)	0.1052 (15)
F25	0.4106 (3)	0.2649 (4)	0.42035 (17)	0.0807 (11)
F26	0.4822 (5)	0.1461 (4)	0.3489 (3)	0.134 (2)
N200	0.8799 (7)	0.0600 (8)	0.3056 (6)	0.149 (4)
C201	0.7923 (8)	0.0335 (5)	0.2890 (4)	0.083 (2)
C202	0.6818 (7)	0.0013 (7)	0.2705 (4)	0.095 (2)
H20A	0.6639	−0.0804	0.2956	0.143*
H20B	0.6895	0.0032	0.2215	0.143*
H20C	0.6158	0.0589	0.2814	0.143*
N300	0.6186 (8)	0.7019 (8)	0.3728 (4)	0.115 (4)	0.852 (11)
C301	0.5552 (7)	0.6772 (10)	0.4114 (4)	0.094 (3)	0.852 (11)
C302	0.4552 (18)	0.6296 (16)	0.4684 (10)	0.226 (9)*	0.852 (11)
H30A	0.4254	0.6941	0.4924	0.340*	0.852 (11)
H30B	0.4888	0.5606	0.5004	0.340*	0.852 (11)
H30C	0.3880	0.6041	0.4483	0.340*	0.852 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.01780 (13)	0.02025 (13)	0.01547 (12)	−0.00351 (9)	−0.00124 (9)	−0.00340 (9)
P1	0.0217 (4)	0.0254 (4)	0.0219 (4)	−0.0036 (3)	−0.0001 (3)	−0.0083 (3)
P2	0.0215 (4)	0.0236 (4)	0.0166 (4)	−0.0023 (3)	−0.0028 (3)	−0.0046 (3)
N1	0.0255 (16)	0.0276 (14)	0.0201 (14)	−0.0059 (12)	−0.0026 (11)	−0.0044 (11)
N2	0.0201 (15)	0.0308 (15)	0.0194 (14)	−0.0036 (12)	−0.0037 (11)	−0.0046 (11)
N3	0.0177 (14)	0.0252 (14)	0.0219 (14)	−0.0021 (11)	−0.0013 (11)	−0.0048 (11)
N4	0.0154 (14)	0.0252 (14)	0.0220 (14)	−0.0003 (11)	−0.0003 (11)	−0.0018 (11)
C1	0.0240 (17)	0.0262 (16)	0.0161 (15)	−0.0055 (13)	−0.0041 (13)	−0.0026 (12)
C2	0.036 (2)	0.0240 (17)	0.033 (2)	−0.0044 (15)	0.0054 (16)	−0.0044 (15)
C3	0.040 (2)	0.040 (2)	0.041 (2)	0.0041 (18)	−0.0026 (19)	0.0013 (18)
C4	0.0293 (19)	0.0350 (19)	0.0197 (16)	−0.0143 (15)	−0.0004 (14)	−0.0025 (14)
C5	0.0194 (17)	0.0381 (19)	0.0191 (16)	−0.0084 (14)	−0.0014 (13)	−0.0029 (14)
C6	0.0195 (17)	0.0313 (18)	0.0280 (18)	0.0004 (14)	−0.0037 (14)	−0.0037 (14)
C7	0.0233 (19)	0.0316 (18)	0.037 (2)	0.0020 (14)	0.0004 (15)	−0.0144 (16)
C11	0.0280 (19)	0.0268 (17)	0.038 (2)	−0.0044 (15)	0.0049 (16)	−0.0161 (15)
C12	0.039 (2)	0.041 (2)	0.049 (3)	−0.0104 (19)	−0.0021 (19)	−0.0183 (19)
C13	0.051 (3)	0.045 (3)	0.085 (4)	−0.019 (2)	−0.001 (3)	−0.025 (3)
C14	0.055 (3)	0.029 (2)	0.103 (5)	−0.016 (2)	0.015 (3)	−0.020 (3)
C15	0.042 (3)	0.029 (2)	0.085 (4)	0.0002 (19)	0.010 (3)	0.000 (2)
C16	0.041 (2)	0.0262 (18)	0.048 (2)	−0.0008 (17)	0.0039 (19)	−0.0055 (17)
C21	0.0233 (18)	0.040 (2)	0.0210 (17)	−0.0080 (15)	−0.0005 (14)	−0.0111 (15)
C22	0.031 (2)	0.061 (3)	0.032 (2)	−0.0025 (19)	−0.0003 (17)	−0.021 (2)
C23	0.046 (3)	0.093 (4)	0.025 (2)	−0.013 (3)	0.0034 (19)	−0.025 (2)
C24	0.051 (3)	0.088 (4)	0.023 (2)	−0.019 (3)	−0.0053 (19)	−0.005 (2)
C25	0.054 (3)	0.056 (3)	0.037 (2)	−0.009 (2)	−0.014 (2)	0.001 (2)
C26	0.038 (2)	0.043 (2)	0.0251 (19)	−0.0060 (18)	−0.0043 (16)	−0.0071 (16)
C31	0.0152 (15)	0.0223 (15)	0.0224 (16)	0.0003 (12)	−0.0001 (12)	−0.0059 (13)
C32	0.029 (2)	0.0331 (18)	0.0267 (18)	−0.0038 (15)	−0.0117 (15)	−0.0027 (15)
C33	0.0221 (19)	0.035 (2)	0.041 (2)	−0.0003 (15)	−0.0095 (16)	−0.0027 (17)
C34	0.0209 (17)	0.0271 (17)	0.0292 (18)	−0.0048 (14)	0.0022 (14)	−0.0031 (14)
C35	0.0190 (17)	0.0252 (16)	0.0294 (18)	−0.0053 (13)	0.0014 (14)	0.0013 (14)
C36	0.0231 (18)	0.0273 (17)	0.0237 (17)	−0.0033 (14)	−0.0059 (14)	0.0006 (13)
C37	0.035 (2)	0.0307 (18)	0.0183 (16)	−0.0052 (15)	−0.0068 (14)	−0.0004 (14)
C41	0.0206 (17)	0.0292 (17)	0.0208 (16)	−0.0055 (13)	−0.0052 (13)	−0.0056 (13)
C42	0.0280 (19)	0.0326 (18)	0.0224 (17)	−0.0025 (15)	−0.0049 (14)	−0.0108 (14)
C43	0.0185 (18)	0.050 (2)	0.0310 (19)	−0.0053 (16)	−0.0038 (15)	−0.0132 (17)
C44	0.037 (2)	0.040 (2)	0.0292 (19)	−0.0187 (18)	−0.0048 (16)	−0.0021 (16)
C45	0.045 (2)	0.0256 (18)	0.036 (2)	−0.0063 (16)	−0.0165 (18)	−0.0016 (15)
C46	0.0286 (19)	0.0278 (17)	0.0307 (19)	0.0002 (14)	−0.0114 (15)	−0.0046 (14)
C51	0.0209 (17)	0.0302 (17)	0.0222 (16)	−0.0044 (14)	−0.0019 (13)	−0.0090 (14)
C52	0.033 (2)	0.050 (2)	0.0253 (19)	0.0013 (18)	−0.0042 (16)	−0.0124 (17)
C53	0.042 (3)	0.058 (3)	0.035 (2)	0.004 (2)	0.0067 (19)	−0.021 (2)
C54	0.023 (2)	0.050 (2)	0.047 (2)	0.0045 (17)	0.0025 (17)	−0.019 (2)
C55	0.0247 (19)	0.036 (2)	0.042 (2)	0.0003 (15)	−0.0078 (16)	−0.0120 (17)
C56	0.0204 (17)	0.0314 (18)	0.0274 (18)	−0.0026 (14)	−0.0020 (14)	−0.0076 (14)
P10	0.0195 (4)	0.0224 (4)	0.0318 (5)	−0.0031 (3)	−0.0055 (4)	−0.0006 (4)
F11	0.0470 (15)	0.0263 (11)	0.0493 (14)	0.0035 (10)	−0.0139 (12)	−0.0057 (10)
F12	0.0409 (14)	0.0265 (11)	0.0612 (16)	0.0034 (10)	−0.0146 (12)	−0.0085 (11)
F13	0.0283 (12)	0.0513 (14)	0.0342 (12)	−0.0092 (10)	0.0001 (10)	−0.0005 (10)
F14	0.0313 (12)	0.0439 (13)	0.0414 (13)	−0.0072 (10)	−0.0152 (10)	−0.0065 (10)
F15	0.0304 (12)	0.0381 (12)	0.0483 (14)	−0.0049 (10)	−0.0179 (10)	−0.0049 (10)
F16	0.0357 (14)	0.0526 (15)	0.0412 (14)	−0.0110 (11)	0.0058 (11)	−0.0023 (11)
P20	0.0336 (6)	0.0489 (6)	0.0426 (6)	−0.0133 (5)	−0.0027 (5)	−0.0088 (5)
F21	0.079 (2)	0.0559 (18)	0.070 (2)	−0.0091 (16)	0.0168 (17)	−0.0225 (16)
F22	0.060 (2)	0.099 (3)	0.061 (2)	0.0021 (18)	−0.0164 (16)	0.0151 (18)
F23	0.0574 (18)	0.0743 (19)	0.0451 (16)	−0.0043 (15)	0.0051 (13)	−0.0207 (14)
F24	0.045 (2)	0.204 (5)	0.070 (2)	−0.003 (2)	−0.0208 (17)	−0.031 (3)
F25	0.064 (2)	0.102 (3)	0.064 (2)	−0.0207 (19)	0.0251 (17)	0.0010 (19)
F26	0.142 (4)	0.080 (3)	0.194 (5)	−0.070 (3)	0.053 (4)	−0.070 (3)
N200	0.083 (5)	0.134 (7)	0.256 (12)	−0.020 (5)	−0.010 (6)	−0.094 (7)
C201	0.107 (6)	0.046 (3)	0.090 (5)	0.000 (4)	0.019 (4)	−0.018 (3)
C202	0.083 (5)	0.089 (5)	0.125 (7)	−0.010 (4)	0.006 (5)	−0.053 (5)
N300	0.104 (6)	0.121 (7)	0.088 (5)	0.024 (5)	0.051 (5)	0.008 (5)
C301	0.053 (5)	0.179 (10)	0.059 (5)	−0.013 (5)	0.005 (4)	−0.047 (6)

Geometric parameters (Å, º) top

Pd1—C31	2.031 (3)	C32—C33	1.504 (5)
Pd1—C1	2.033 (3)	C32—H32A	0.9900
Pd1—P1	2.3085 (9)	C32—H32B	0.9900
Pd1—P2	2.3100 (9)	C33—H33A	0.9800
P1—C21	1.806 (4)	C33—H33B	0.9800
P1—C11	1.811 (4)	C33—H33C	0.9800
P1—C7	1.848 (4)	C34—C35	1.344 (5)
P2—C51	1.805 (4)	C34—H34A	0.9500
P2—C41	1.815 (3)	C35—H35A	0.9500
P2—C37	1.847 (3)	C36—C37	1.523 (5)
N1—C1	1.347 (4)	C36—H36A	0.9900
N1—C4	1.387 (5)	C36—H36B	0.9900
N1—C2	1.467 (5)	C37—H37A	0.9900
N2—C1	1.347 (5)	C37—H37B	0.9900
N2—C5	1.379 (4)	C41—C46	1.383 (5)
N2—C6	1.466 (4)	C41—C42	1.395 (5)
N3—C31	1.348 (4)	C42—C43	1.391 (5)
N3—C34	1.386 (4)	C42—H42A	0.9500
N3—C32	1.467 (4)	C43—C44	1.381 (6)
N4—C31	1.347 (4)	C43—H43A	0.9500
N4—C35	1.387 (4)	C44—C45	1.389 (6)
N4—C36	1.459 (4)	C44—H44A	0.9500
C2—C3	1.512 (6)	C45—C46	1.391 (5)
C2—H2A	0.9900	C45—H45A	0.9500
C2—H2B	0.9900	C46—H46A	0.9500
C3—H3A	0.9800	C51—C56	1.391 (5)
C3—H3B	0.9800	C51—C52	1.400 (5)
C3—H3C	0.9800	C52—C53	1.383 (6)
C4—C5	1.339 (5)	C52—H52A	0.9500
C4—H4A	0.9500	C53—C54	1.375 (6)
C5—H5A	0.9500	C53—H53A	0.9500
C6—C7	1.528 (5)	C54—C55	1.382 (6)
C6—H6A	0.9900	C54—H54A	0.9500
C6—H6B	0.9900	C55—C56	1.397 (5)
C7—H7A	0.9900	C55—H55A	0.9500
C7—H7B	0.9900	C56—H56A	0.9500
C11—C12	1.386 (6)	P10—F16	1.584 (2)
C11—C16	1.392 (6)	P10—F14	1.595 (2)
C12—C13	1.384 (6)	P10—F12	1.601 (2)
C12—H12A	0.9500	P10—F13	1.603 (2)
C13—C14	1.362 (8)	P10—F11	1.603 (2)
C13—H13A	0.9500	P10—F15	1.605 (2)
C14—C15	1.371 (8)	P20—F26	1.558 (4)
C14—H14A	0.9500	P20—F22	1.569 (3)
C15—C16	1.396 (6)	P20—F24	1.577 (4)
C15—H15A	0.9500	P20—F21	1.583 (3)
C16—H16A	0.9500	P20—F23	1.586 (3)
C21—C22	1.391 (5)	P20—F25	1.598 (3)
C21—C26	1.392 (6)	N200—C201	1.147 (10)
C22—C23	1.390 (6)	C201—C202	1.421 (11)
C22—H22A	0.9500	C202—H20A	0.9800
C23—C24	1.359 (8)	C202—H20B	0.9800
C23—H23A	0.9500	C202—H20C	0.9800
C24—C25	1.378 (7)	N300—C301	1.000 (9)
C24—H24A	0.9500	C301—C302	1.549 (19)
C25—C26	1.391 (6)	C302—H30A	0.9800
C25—H25A	0.9500	C302—H30B	0.9800
C26—H26A	0.9500	C302—H30C	0.9800

C31—Pd1—C1	173.56 (13)	C33—C32—H32B	109.4
C31—Pd1—P1	94.24 (9)	H32A—C32—H32B	108.0
C1—Pd1—P1	84.03 (10)	C32—C33—H33A	109.5
C31—Pd1—P2	83.54 (9)	C32—C33—H33B	109.5
C1—Pd1—P2	96.46 (10)	H33A—C33—H33B	109.5
P1—Pd1—P2	164.44 (3)	C32—C33—H33C	109.5
C21—P1—C11	105.73 (18)	H33A—C33—H33C	109.5
C21—P1—C7	105.68 (18)	H33B—C33—H33C	109.5
C11—P1—C7	106.11 (17)	C35—C34—N3	107.0 (3)
C21—P1—Pd1	117.44 (13)	C35—C34—H34A	126.5
C11—P1—Pd1	115.02 (12)	N3—C34—H34A	126.5
C7—P1—Pd1	105.96 (12)	C34—C35—N4	106.4 (3)
C51—P2—C41	106.27 (16)	C34—C35—H35A	126.8
C51—P2—C37	107.06 (17)	N4—C35—H35A	126.8
C41—P2—C37	105.51 (16)	N4—C36—C37	111.9 (3)
C51—P2—Pd1	115.17 (11)	N4—C36—H36A	109.2
C41—P2—Pd1	115.95 (11)	C37—C36—H36A	109.2
C37—P2—Pd1	106.15 (12)	N4—C36—H36B	109.2
C1—N1—C4	110.3 (3)	C37—C36—H36B	109.2
C1—N1—C2	125.6 (3)	H36A—C36—H36B	107.9
C4—N1—C2	124.1 (3)	C36—C37—P2	114.2 (2)
C1—N2—C5	110.7 (3)	C36—C37—H37A	108.7
C1—N2—C6	123.4 (3)	P2—C37—H37A	108.7
C5—N2—C6	125.8 (3)	C36—C37—H37B	108.7
C31—N3—C34	110.5 (3)	P2—C37—H37B	108.7
C31—N3—C32	125.8 (3)	H37A—C37—H37B	107.6
C34—N3—C32	123.5 (3)	C46—C41—C42	119.2 (3)
C31—N4—C35	110.9 (3)	C46—C41—P2	123.0 (3)
C31—N4—C36	122.6 (3)	C42—C41—P2	117.6 (3)
C35—N4—C36	126.5 (3)	C43—C42—C41	120.5 (3)
N1—C1—N2	105.3 (3)	C43—C42—H42A	119.8
N1—C1—Pd1	133.2 (3)	C41—C42—H42A	119.8
N2—C1—Pd1	121.5 (2)	C44—C43—C42	119.5 (4)
N1—C2—C3	111.9 (3)	C44—C43—H43A	120.2
N1—C2—H2A	109.2	C42—C43—H43A	120.2
C3—C2—H2A	109.2	C43—C44—C45	120.7 (4)
N1—C2—H2B	109.2	C43—C44—H44A	119.7
C3—C2—H2B	109.2	C45—C44—H44A	119.7
H2A—C2—H2B	107.9	C44—C45—C46	119.3 (4)
C2—C3—H3A	109.5	C44—C45—H45A	120.3
C2—C3—H3B	109.5	C46—C45—H45A	120.3
H3A—C3—H3B	109.5	C41—C46—C45	120.8 (4)
C2—C3—H3C	109.5	C41—C46—H46A	119.6
H3A—C3—H3C	109.5	C45—C46—H46A	119.6
H3B—C3—H3C	109.5	C56—C51—C52	119.0 (3)
C5—C4—N1	106.9 (3)	C56—C51—P2	119.1 (3)
C5—C4—H4A	126.6	C52—C51—P2	121.9 (3)
N1—C4—H4A	126.6	C53—C52—C51	119.9 (4)
C4—C5—N2	106.9 (3)	C53—C52—H52A	120.0
C4—C5—H5A	126.6	C51—C52—H52A	120.0
N2—C5—H5A	126.6	C54—C53—C52	120.9 (4)
N2—C6—C7	112.6 (3)	C54—C53—H53A	119.5
N2—C6—H6A	109.1	C52—C53—H53A	119.5
C7—C6—H6A	109.1	C53—C54—C55	120.0 (4)
N2—C6—H6B	109.1	C53—C54—H54A	120.0
C7—C6—H6B	109.1	C55—C54—H54A	120.0
H6A—C6—H6B	107.8	C54—C55—C56	119.7 (4)
C6—C7—P1	114.3 (2)	C54—C55—H55A	120.1
C6—C7—H7A	108.7	C56—C55—H55A	120.1
P1—C7—H7A	108.7	C51—C56—C55	120.4 (3)
C6—C7—H7B	108.7	C51—C56—H56A	119.8
P1—C7—H7B	108.7	C55—C56—H56A	119.8
H7A—C7—H7B	107.6	F16—P10—F14	90.43 (14)
C12—C11—C16	119.9 (4)	F16—P10—F12	90.52 (14)
C12—C11—P1	121.1 (3)	F14—P10—F12	90.56 (13)
C16—C11—P1	118.5 (3)	F16—P10—F13	179.76 (15)
C13—C12—C11	119.8 (5)	F14—P10—F13	89.78 (13)
C13—C12—H12A	120.1	F12—P10—F13	89.59 (14)
C11—C12—H12A	120.1	F16—P10—F11	90.12 (14)
C14—C13—C12	120.4 (5)	F14—P10—F11	89.97 (13)
C14—C13—H13A	119.8	F12—P10—F11	179.17 (14)
C12—C13—H13A	119.8	F13—P10—F11	89.78 (14)
C13—C14—C15	120.4 (4)	F16—P10—F15	90.59 (14)
C13—C14—H14A	119.8	F14—P10—F15	178.91 (14)
C15—C14—H14A	119.8	F12—P10—F15	89.80 (13)
C14—C15—C16	120.5 (5)	F13—P10—F15	89.20 (13)
C14—C15—H15A	119.8	F11—P10—F15	89.66 (13)
C16—C15—H15A	119.8	F26—P20—F22	90.2 (3)
C11—C16—C15	118.9 (5)	F26—P20—F24	92.2 (3)
C11—C16—H16A	120.5	F22—P20—F24	177.4 (3)
C15—C16—H16A	120.5	F26—P20—F21	178.2 (3)
C22—C21—C26	119.7 (4)	F22—P20—F21	88.5 (2)
C22—C21—P1	120.1 (3)	F24—P20—F21	89.0 (2)
C26—C21—P1	120.2 (3)	F26—P20—F23	91.7 (2)
C23—C22—C21	119.9 (5)	F22—P20—F23	89.29 (18)
C23—C22—H22A	120.1	F24—P20—F23	89.78 (19)
C21—C22—H22A	120.1	F21—P20—F23	89.62 (17)
C24—C23—C22	119.8 (4)	F26—P20—F25	89.6 (2)
C24—C23—H23A	120.1	F22—P20—F25	91.9 (2)
C22—C23—H23A	120.1	F24—P20—F25	88.9 (2)
C23—C24—C25	121.4 (4)	F21—P20—F25	89.04 (19)
C23—C24—H24A	119.3	F23—P20—F25	178.2 (2)
C25—C24—H24A	119.3	N200—C201—C202	178.2 (9)
C24—C25—C26	119.5 (5)	C201—C202—H20A	109.5
C24—C25—H25A	120.2	C201—C202—H20B	109.5
C26—C25—H25A	120.2	H20A—C202—H20B	109.5
C25—C26—C21	119.6 (4)	C201—C202—H20C	109.5
C25—C26—H26A	120.2	H20A—C202—H20C	109.5
C21—C26—H26A	120.2	H20B—C202—H20C	109.5
N4—C31—N3	105.2 (3)	N300—C301—C302	175.1 (14)
N4—C31—Pd1	121.4 (2)	C301—C302—H30A	109.5
N3—C31—Pd1	133.0 (2)	C301—C302—H30B	109.5
N3—C32—C33	111.4 (3)	H30A—C302—H30B	109.5
N3—C32—H32A	109.4	C301—C302—H30C	109.5
C33—C32—H32A	109.4	H30A—C302—H30C	109.5
N3—C32—H32B	109.4	H30B—C302—H30C	109.5

C31—Pd1—P1—C21	−121.77 (16)	Pd1—P1—C21—C26	11.0 (4)
C1—Pd1—P1—C21	64.46 (16)	C26—C21—C22—C23	−0.6 (6)
P2—Pd1—P1—C21	157.10 (16)	P1—C21—C22—C23	−179.7 (3)
C31—Pd1—P1—C11	3.65 (18)	C21—C22—C23—C24	−0.6 (7)
C1—Pd1—P1—C11	−170.13 (18)	C22—C23—C24—C25	1.4 (8)
P2—Pd1—P1—C11	−77.49 (19)	C23—C24—C25—C26	−0.9 (7)
C31—Pd1—P1—C7	120.51 (16)	C24—C25—C26—C21	−0.3 (7)
C1—Pd1—P1—C7	−53.27 (16)	C22—C21—C26—C25	1.0 (6)
P2—Pd1—P1—C7	39.38 (19)	P1—C21—C26—C25	−179.9 (3)
C31—Pd1—P2—C51	67.33 (16)	C35—N4—C31—N3	−1.1 (4)
C1—Pd1—P2—C51	−119.15 (16)	C36—N4—C31—N3	178.9 (3)
P1—Pd1—P2—C51	149.91 (16)	C35—N4—C31—Pd1	173.0 (2)
C31—Pd1—P2—C41	−167.71 (16)	C36—N4—C31—Pd1	−7.0 (4)
C1—Pd1—P2—C41	5.81 (16)	C34—N3—C31—N4	1.2 (4)
P1—Pd1—P2—C41	−85.13 (17)	C32—N3—C31—N4	−173.9 (3)
C31—Pd1—P2—C37	−50.94 (16)	C34—N3—C31—Pd1	−171.9 (3)
C1—Pd1—P2—C37	122.58 (16)	C32—N3—C31—Pd1	13.0 (5)
P1—Pd1—P2—C37	31.64 (19)	P1—Pd1—C31—N4	−107.3 (3)
C4—N1—C1—N2	1.3 (4)	P2—Pd1—C31—N4	57.2 (3)
C2—N1—C1—N2	−179.1 (3)	P1—Pd1—C31—N3	64.8 (3)
C4—N1—C1—Pd1	−175.5 (3)	P2—Pd1—C31—N3	−130.6 (3)
C2—N1—C1—Pd1	4.1 (5)	C31—N3—C32—C33	108.9 (4)
C5—N2—C1—N1	−1.3 (4)	C34—N3—C32—C33	−65.6 (4)
C6—N2—C1—N1	−178.1 (3)	C31—N3—C34—C35	−0.8 (4)
C5—N2—C1—Pd1	175.9 (2)	C32—N3—C34—C35	174.4 (3)
C6—N2—C1—Pd1	−0.9 (4)	N3—C34—C35—N4	0.1 (4)
P1—Pd1—C1—N1	−130.2 (3)	C31—N4—C35—C34	0.6 (4)
P2—Pd1—C1—N1	65.4 (3)	C36—N4—C35—C34	−179.4 (3)
P1—Pd1—C1—N2	53.4 (3)	C31—N4—C36—C37	−63.7 (4)
P2—Pd1—C1—N2	−110.9 (3)	C35—N4—C36—C37	116.4 (4)
C1—N1—C2—C3	120.2 (4)	N4—C36—C37—P2	52.2 (4)
C4—N1—C2—C3	−60.2 (5)	C51—P2—C37—C36	−113.4 (3)
C1—N1—C4—C5	−0.8 (4)	C41—P2—C37—C36	133.7 (3)
C2—N1—C4—C5	179.6 (3)	Pd1—P2—C37—C36	10.2 (3)
N1—C4—C5—N2	−0.1 (4)	C51—P2—C41—C46	6.3 (3)
C1—N2—C5—C4	0.9 (4)	C37—P2—C41—C46	119.8 (3)
C6—N2—C5—C4	177.6 (3)	Pd1—P2—C41—C46	−123.1 (3)
C1—N2—C6—C7	−65.3 (4)	C51—P2—C41—C42	−179.2 (3)
C5—N2—C6—C7	118.4 (4)	C37—P2—C41—C42	−65.8 (3)
N2—C6—C7—P1	46.9 (4)	Pd1—P2—C41—C42	51.4 (3)
C21—P1—C7—C6	−109.5 (3)	C46—C41—C42—C43	2.8 (5)
C11—P1—C7—C6	138.5 (3)	P2—C41—C42—C43	−171.8 (3)
Pd1—P1—C7—C6	15.8 (3)	C41—C42—C43—C44	−1.1 (5)
C21—P1—C11—C12	20.4 (4)	C42—C43—C44—C45	−1.2 (6)
C7—P1—C11—C12	132.4 (3)	C43—C44—C45—C46	1.6 (6)
Pd1—P1—C11—C12	−110.9 (3)	C42—C41—C46—C45	−2.4 (5)
C21—P1—C11—C16	−167.6 (3)	P2—C41—C46—C45	172.0 (3)
C7—P1—C11—C16	−55.7 (3)	C44—C45—C46—C41	0.2 (6)
Pd1—P1—C11—C16	61.1 (3)	C41—P2—C51—C56	−107.9 (3)
C16—C11—C12—C13	0.8 (6)	C37—P2—C51—C56	139.7 (3)
P1—C11—C12—C13	172.6 (4)	Pd1—P2—C51—C56	21.9 (3)
C11—C12—C13—C14	−1.8 (7)	C41—P2—C51—C52	69.9 (3)
C12—C13—C14—C15	1.4 (8)	C37—P2—C51—C52	−42.5 (4)
C13—C14—C15—C16	0.0 (8)	Pd1—P2—C51—C52	−160.2 (3)
C12—C11—C16—C15	0.6 (6)	C56—C51—C52—C53	−0.2 (6)
P1—C11—C16—C15	−171.4 (3)	P2—C51—C52—C53	−178.1 (3)
C14—C15—C16—C11	−1.0 (7)	C51—C52—C53—C54	−0.2 (7)
C11—P1—C21—C22	60.2 (3)	C52—C53—C54—C55	−0.1 (7)
C7—P1—C21—C22	−52.0 (3)	C53—C54—C55—C56	0.7 (6)
Pd1—P1—C21—C22	−169.9 (3)	C52—C51—C56—C55	0.8 (5)
C11—P1—C21—C26	−118.9 (3)	P2—C51—C56—C55	178.8 (3)
C7—P1—C21—C26	128.9 (3)	C54—C55—C56—C51	−1.1 (6)

Experimental details

Crystal data
Chemical formula	[Pd(C₁₉H₂₁N₂P)₂](PF₆)₂·2.85C₂H₃N
M_r	1130.45
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	11.114 (2), 11.343 (2), 20.243 (4)
α, β, γ (°)	77.490 (4), 83.580 (5), 85.301 (4)
V (Å³)	2471.4 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.42 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.790, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	20500, 10802, 9025
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.129, 1.05
No. of reflections	10802
No. of parameters	584
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −0.56

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Pd1—C31	2.031 (3)	Pd1—P1	2.3085 (9)
Pd1—C1	2.033 (3)	Pd1—P2	2.3100 (9)

C31—Pd1—C1	173.56 (13)	C31—Pd1—P2	83.54 (9)
C31—Pd1—P1	94.24 (9)	C1—Pd1—P2	96.46 (10)
C1—Pd1—P1	84.03 (10)	P1—Pd1—P2	164.44 (3)

References

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