cis-{2,6-Bis[(di-tert-butyl­phosphan­yl)meth­yl]cyclo­hexyl-κ3P,C1,P′}chloridopalladium(II)

Olsson, D.; Janse van Rensburg, J.M.; Wendt, O.F.

doi:10.1107/S1600536812047022

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1513

doi:10.1107/S1600536812047022

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cis-{2,6-Bis[(di-tert-butylphosphanyl)methyl]cyclohexyl-κ³P,C¹,P′}chloridopalladium(II)

Daniel Olsson,^a J. Marthinus Janse van Rensburg ^a and Ola F. Wendt ^a ^*

^aCentre for Analysis and Synthesis, Department of Chemistry, Lund University, PO Box 124, S-221 00 Lund, Sweden
^*Correspondence e-mail: ola.wendt@chem.lu.se

(Received 8 November 2012; accepted 15 November 2012; online 24 November 2012)

The Pd^II atom in the title compound, [Pd(C₂₄H₄₉P₂)Cl], has a distorted square-planar CClP₂ coordination geometry with the P,C,P′-tridentate ligand forming two five-membered metallacycles. The cyclohexane ring is aligned with the Pd^II coordination plane due to C—H activation in an equatorial position, giving a tri-equatorial conformation of the cyclohexyl ring.

Related literature

C(sp³)—H activated (PCP)-complexes with catalytic performance in C—C coupling reactions were reported by Ohff et al. (1997 ); Sjövall et al. (2002 ); Nilsson & Wendt (2005 ); Olsson & Wendt (2009 ). Metal complexes with (PCP)-type ligands containing an aliphatic backbone have been reported for Rh (Kuznetsov et al., 2006 ), Ni (Castonguay et al., 2006 ; Pandarus & Zargarian, 2007 ), Pt (Olsson et al. 2007a ), Ir (Arunachalampillai et al., 2009 ; Jonasson et al. 2011 ). The crystal structures of the bromide and iodide analogues of the title compound were determined by Sjövall et al. (2002) and Olsson et al. (2007b ).

Experimental

Crystal data

[Pd(C₂₄H₄₉P₂)Cl]
M_r = 541.42
Monoclinic, P 2₁ /n
a = 11.9467 (2) Å
b = 14.6159 (2) Å
c = 15.5190 (3) Å
β = 100.339 (2)°
V = 2665.80 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 293 K
0.15 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction XCalibur 3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.941, T_max = 1.000
26794 measured reflections
9297 independent reflections
6699 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.070
S = 0.96
9297 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 1.28 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (CrystalMaker, 2011 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812047022/wm2700sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047022/wm2700Isup2.hkl

checkCIF report

Comment top

In this study we report the crystal structure of {cis-1,3-bis[(di-tert-butylphosphanyl)methyl]cyclohexane}palladium(II) chloride, [PdCl(C₂₄H₄₉P₂)], (I).

Compound (I) belongs to a family of C(sp³)—H activated (PCP)-complexes, showing interesting catalytic performance in C—C coupling reactions (Ohff et al., 1997; Sjövall et al., 2002; Nilsson & Wendt, 2005; Olsson & Wendt, 2009). Structural data for the corresponding bromide and iodide analogues have been reported previously (Sjövall et al., 2002; Olsson et al., 2007b).

Aromatic backbones are by far the most commonly occurring for palladium (PCP)-complexes, but complexes based on an aliphatic backbone are receiving increasing attention. Aliphatic (PCP)-type ligands that are coordinated to transition metals have been published recently for metals such as rhodium (Kuznetsov et al., 2006), nickel (Castonguay et al., 2006; Pandarus & Zargarian, 2007), platinum (Olsson et al. 2007a) and iridium (Arunachalampillai et al., 2009; Jonasson et al. 2011).

In the structure of (I) the Pd^II atom exhibits a pseudo-square-planar coordination geometry (Fig. 1). Comparison to the analogous iodido and bromido complexes indicates the expected Pd—halogen bond lengths decrease. The Pd—P bond lengths are around 2.3 Å in all complexes with a trans orientation of the P atoms; in (I) the P1—Pd1—P2 angle is 166.495 (15) ° . The (PCP)-tridentate ligand and the Pd^II atom form two five-membered metalla rings. As is usually observed in these systems, the bis-chelating system displays two acute P—Pd—C1 angles of around 83–84°. Bond lengths are Pd1—Cl1, 2.4405 (4) Å, Pd1—P1, 2.3233 (4) Å, Pd1—P2, 2.3226 (4) Å and Pd1—C1, 2.0808 (16) Å.

The cyclohexane ring is aligned with the palladium coordination plane forming the usual tri-equatorial conformation (Fig. 1).

Related literature top

C(sp³)—H activated (PCP)-complexes with catalytic performance in C—C coupling reactions were reported by Ohff et al. (1997); Sjövall et al. (2002); Nilsson & Wendt (2005); Olsson & Wendt (2009). Metal complexes with (PCP)-type ligands containing an aliphatic backbone have been reported for Rh (Kuznetsov et al., 2006), Ni (Castonguay et al., 2006; Pandarus & Zargarian, 2007), Pt (Olsson et al. 2007a), Ir (Arunachalampillai et al., 2009; Jonasson et al. 2011). The crystal structures of the bromide and iodide analogues of the title compound were determined by Sjövall et al. (2002) and Olsson et al. (2007b).

Experimental top

All procedures were performed under vacuum or nitrogen. The (PCP)H ligand was prepared according to the published procedure (Sjövall et al., 2002). A solution of the ligand (0.536 g, 1.337 mmol) in 20 ml THF was mixed with a solution of PdCl₂(PhCN)₂ (0.500 g, 1.304 mmol) in 30 ml THF in a high-pressure glass vessel and the mixture was heated at 353 K for 8 h. Evaporation of all volatiles gave a crude, light yellow product in almost quantitative yield. Recrystallization from hexane gave 0.483 g (69%) of crystals suitable for X-ray crystallographic analysis. ¹H-NMR (benzene-d₆): δ 2.15–0.80 (m region, 13H, CH & CH₂), 1.37 (m, 36H, coalesced virtual triplets). ³¹P{¹H} NMR (benzene-d₆): δ 70.6 (s).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (CrystalMaker, 2011); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with atom labels (methyl groups labels omitted) and 40% probability displacement ellipsoids. H-atoms were omitted for clarity.

cis-{2,6-Bis[(di-tert- butylphosphanyl)methyl]cyclohexyl- κ³P,C¹,P'}chloridopalladium(II) top

Crystal data top

[Pd(C₂₄H₄₉P₂)Cl]	F(000) = 1144
M_r = 541.42	D_x = 1.349 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 14595 reflections
a = 11.9467 (2) Å	θ = 2.2–33.0°
b = 14.6159 (2) Å	µ = 0.93 mm⁻¹
c = 15.5190 (3) Å	T = 293 K
β = 100.339 (2)°	Prism, colourless
V = 2665.80 (8) Å³	0.15 × 0.10 × 0.05 mm
Z = 4

Data collection top

Oxford Diffraction XCalibur 3 diffractometer	9297 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6699 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 16.1829 pixels mm^-1	θ_max = 33.0°, θ_min = 2.2°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −20→22
T_min = 0.941, T_max = 1.000	l = −17→23
26794 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
9297 reflections	(Δ/σ)_max = 0.004
253 parameters	Δρ_max = 1.28 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Pd(C₂₄H₄₉P₂)Cl]	V = 2665.80 (8) Å³
M_r = 541.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.9467 (2) Å	µ = 0.93 mm⁻¹
b = 14.6159 (2) Å	T = 293 K
c = 15.5190 (3) Å	0.15 × 0.10 × 0.05 mm
β = 100.339 (2)°

Data collection top

Oxford Diffraction XCalibur 3 diffractometer	9297 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	6699 reflections with I > 2σ(I)
T_min = 0.941, T_max = 1.000	R_int = 0.024
26794 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 0.96	Δρ_max = 1.28 e Å⁻³
9297 reflections	Δρ_min = −0.56 e Å⁻³
253 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	0.395006 (10)	0.557045 (8)	0.252150 (7)	0.01343 (4)
Cl1	0.36623 (3)	0.67441 (3)	0.35789 (3)	0.02067 (8)
P1	0.20462 (4)	0.53783 (3)	0.18983 (3)	0.01455 (8)
P2	0.59247 (3)	0.55763 (3)	0.28541 (3)	0.01541 (8)
C1	0.41983 (14)	0.46752 (12)	0.15303 (11)	0.0188 (3)
H1	0.4226	0.5065	0.1021	0.023*
C2	0.32136 (14)	0.40129 (11)	0.12327 (11)	0.0197 (3)
H2	0.3176	0.3597	0.1722	0.024*
C3	0.33987 (15)	0.34263 (12)	0.04548 (10)	0.0210 (3)
H3A	0.2794	0.2977	0.0332	0.025*
H3B	0.3356	0.3813	−0.0058	0.025*
C4	0.45339 (16)	0.29375 (12)	0.06192 (11)	0.0268 (4)
H4A	0.4642	0.2621	0.0091	0.032*
H4B	0.4539	0.2485	0.1077	0.032*
C5	0.55085 (15)	0.36146 (12)	0.08926 (10)	0.0215 (3)
H5A	0.5551	0.4029	0.0411	0.026*
H5B	0.6222	0.3283	0.1025	0.026*
C6	0.53358 (15)	0.41664 (12)	0.16956 (11)	0.0211 (3)
H6	0.5313	0.3731	0.2172	0.025*
C7	0.20875 (14)	0.45253 (11)	0.10369 (11)	0.0196 (3)
H7A	0.1461	0.4099	0.1016	0.024*
H7B	0.2011	0.4826	0.0472	0.024*
C8	0.63117 (14)	0.48257 (12)	0.20024 (11)	0.0204 (3)
H8A	0.6460	0.5190	0.1513	0.024*
H8B	0.6996	0.4486	0.2236	0.024*
C11	0.11083 (13)	0.48541 (11)	0.26177 (10)	0.0172 (3)
C12	0.16985 (16)	0.39565 (12)	0.29573 (12)	0.0255 (4)
H12A	0.2458	0.4085	0.3254	0.038*
H12B	0.1726	0.3554	0.2473	0.038*
H12C	0.1280	0.3670	0.3357	0.038*
C13	−0.00951 (14)	0.46389 (13)	0.21394 (12)	0.0252 (4)
H13A	−0.0470	0.5197	0.1926	0.038*
H13B	−0.0514	0.4347	0.2536	0.038*
H13C	−0.0057	0.4238	0.1656	0.038*
C14	0.10502 (15)	0.54682 (12)	0.34093 (11)	0.0242 (4)
H14A	0.1807	0.5603	0.3709	0.036*
H14B	0.0640	0.5158	0.3801	0.036*
H14C	0.0666	0.6028	0.3214	0.036*
C15	0.13876 (14)	0.64162 (11)	0.12899 (10)	0.0195 (3)
C16	0.03613 (16)	0.62126 (13)	0.05651 (12)	0.0290 (4)
H16A	0.0577	0.5776	0.0162	0.044*
H16B	0.0114	0.6768	0.0258	0.044*
H16C	−0.0248	0.5967	0.0822	0.044*
C17	0.10405 (16)	0.71136 (12)	0.19252 (12)	0.0261 (4)
H17A	0.1678	0.7241	0.2380	0.039*
H17B	0.0428	0.6870	0.2179	0.039*
H17C	0.0797	0.7668	0.1616	0.039*
C18	0.23380 (16)	0.68321 (12)	0.08639 (12)	0.0271 (4)
H18A	0.2561	0.6400	0.0461	0.041*
H18B	0.2981	0.6975	0.1310	0.041*
H18C	0.2065	0.7380	0.0556	0.041*
C21	0.66048 (14)	0.50577 (12)	0.39318 (11)	0.0200 (3)
C22	0.61384 (17)	0.40707 (12)	0.39274 (12)	0.0286 (4)
H22A	0.6367	0.3732	0.3458	0.043*
H22B	0.5323	0.4087	0.3846	0.043*
H22C	0.6436	0.3780	0.4475	0.043*
C23	0.79068 (15)	0.50157 (16)	0.40666 (12)	0.0321 (4)
H23A	0.8133	0.4693	0.3587	0.048*
H23B	0.8194	0.4703	0.4605	0.048*
H23C	0.8209	0.5626	0.4092	0.048*
C24	0.62365 (15)	0.55715 (12)	0.46951 (11)	0.0235 (3)
H24A	0.5421	0.5601	0.4604	0.035*
H24B	0.6543	0.6180	0.4726	0.035*
H24C	0.6515	0.5255	0.5233	0.035*
C25	0.65819 (14)	0.67117 (11)	0.26587 (11)	0.0199 (3)
C26	0.77759 (15)	0.66373 (13)	0.24310 (13)	0.0304 (4)
H26A	0.7752	0.6242	0.1934	0.046*
H26B	0.8290	0.6390	0.2922	0.046*
H26C	0.8032	0.7234	0.2294	0.046*
C27	0.66061 (16)	0.73466 (12)	0.34422 (12)	0.0268 (4)
H27A	0.5856	0.7391	0.3580	0.040*
H27B	0.6859	0.7943	0.3302	0.040*
H27C	0.7119	0.7105	0.3938	0.040*
C28	0.57787 (16)	0.71338 (13)	0.18684 (12)	0.0276 (4)
H28A	0.5027	0.7187	0.2001	0.041*
H28B	0.5758	0.6748	0.1365	0.041*
H28C	0.6052	0.7729	0.1747	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.01082 (6)	0.01346 (6)	0.01586 (6)	0.00033 (5)	0.00199 (4)	−0.00143 (5)
Cl1	0.01600 (19)	0.0219 (2)	0.02365 (19)	0.00088 (15)	0.00219 (15)	−0.00764 (16)
P1	0.01157 (19)	0.01407 (19)	0.01712 (19)	−0.00003 (14)	0.00017 (15)	−0.00109 (14)
P2	0.01061 (18)	0.01640 (19)	0.01917 (19)	0.00028 (16)	0.00255 (15)	−0.00093 (16)
C1	0.0188 (8)	0.0192 (8)	0.0188 (8)	0.0020 (6)	0.0049 (6)	−0.0017 (6)
C2	0.0209 (9)	0.0182 (8)	0.0196 (8)	0.0019 (6)	0.0025 (7)	−0.0014 (6)
C3	0.0259 (9)	0.0197 (8)	0.0175 (8)	0.0008 (7)	0.0042 (7)	−0.0034 (6)
C4	0.0362 (11)	0.0236 (9)	0.0209 (8)	0.0085 (8)	0.0056 (8)	−0.0020 (7)
C5	0.0229 (9)	0.0228 (9)	0.0197 (8)	0.0079 (7)	0.0062 (7)	0.0017 (7)
C6	0.0217 (9)	0.0217 (8)	0.0195 (8)	0.0049 (7)	0.0022 (7)	−0.0007 (6)
C7	0.0163 (8)	0.0215 (9)	0.0203 (8)	−0.0024 (6)	0.0011 (6)	−0.0014 (6)
C8	0.0156 (8)	0.0221 (9)	0.0243 (8)	0.0041 (6)	0.0058 (7)	0.0012 (7)
C11	0.0130 (7)	0.0148 (8)	0.0246 (8)	−0.0013 (6)	0.0057 (6)	−0.0009 (6)
C12	0.0247 (9)	0.0215 (9)	0.0319 (10)	0.0015 (7)	0.0097 (8)	0.0040 (7)
C13	0.0167 (9)	0.0281 (10)	0.0312 (9)	−0.0050 (7)	0.0051 (7)	−0.0033 (7)
C14	0.0229 (9)	0.0274 (10)	0.0234 (8)	−0.0038 (7)	0.0074 (7)	−0.0028 (7)
C15	0.0183 (8)	0.0168 (8)	0.0213 (8)	0.0009 (6)	−0.0021 (6)	0.0009 (6)
C16	0.0272 (10)	0.0241 (9)	0.0302 (9)	0.0025 (8)	−0.0097 (8)	0.0021 (8)
C17	0.0263 (10)	0.0181 (9)	0.0315 (10)	0.0055 (7)	−0.0014 (8)	0.0006 (7)
C18	0.0288 (10)	0.0225 (9)	0.0300 (9)	0.0003 (8)	0.0052 (8)	0.0073 (7)
C21	0.0148 (8)	0.0236 (9)	0.0208 (8)	0.0022 (7)	0.0012 (6)	−0.0007 (7)
C22	0.0385 (11)	0.0218 (9)	0.0228 (9)	0.0025 (8)	−0.0020 (8)	0.0023 (7)
C23	0.0180 (9)	0.0516 (13)	0.0254 (9)	0.0069 (9)	0.0000 (7)	0.0019 (9)
C24	0.0240 (9)	0.0258 (9)	0.0209 (8)	−0.0009 (7)	0.0044 (7)	0.0000 (7)
C25	0.0145 (8)	0.0199 (8)	0.0258 (8)	−0.0019 (6)	0.0047 (6)	0.0003 (7)
C26	0.0191 (9)	0.0281 (10)	0.0462 (11)	−0.0043 (7)	0.0120 (8)	0.0042 (9)
C27	0.0234 (9)	0.0204 (9)	0.0363 (10)	−0.0062 (7)	0.0044 (8)	−0.0022 (8)
C28	0.0265 (10)	0.0236 (9)	0.0324 (10)	−0.0019 (7)	0.0046 (8)	0.0078 (8)

Geometric parameters (Å, º) top

Pd1—C1	2.0808 (16)	C14—H14A	0.9600
Pd1—P2	2.3226 (4)	C14—H14B	0.9600
Pd1—P1	2.3233 (4)	C14—H14C	0.9600
Pd1—Cl1	2.4405 (4)	C15—C17	1.526 (2)
P1—C7	1.8352 (17)	C15—C16	1.537 (2)
P1—C11	1.8810 (16)	C15—C18	1.538 (2)
P1—C15	1.8828 (17)	C16—H16A	0.9600
P2—C8	1.8394 (17)	C16—H16B	0.9600
P2—C21	1.8827 (17)	C16—H16C	0.9600
P2—C25	1.8835 (17)	C17—H17A	0.9600
C1—C2	1.530 (2)	C17—H17B	0.9600
C1—C6	1.530 (2)	C17—H17C	0.9600
C1—H1	0.9800	C18—H18A	0.9600
C2—C7	1.522 (2)	C18—H18B	0.9600
C2—C3	1.529 (2)	C18—H18C	0.9600
C2—H2	0.9800	C21—C24	1.532 (2)
C3—C4	1.513 (2)	C21—C23	1.533 (2)
C3—H3A	0.9700	C21—C22	1.546 (2)
C3—H3B	0.9700	C22—H22A	0.9600
C4—C5	1.529 (3)	C22—H22B	0.9600
C4—H4A	0.9700	C22—H22C	0.9600
C4—H4B	0.9700	C23—H23A	0.9600
C5—C6	1.529 (2)	C23—H23B	0.9600
C5—H5A	0.9700	C23—H23C	0.9600
C5—H5B	0.9700	C24—H24A	0.9600
C6—C8	1.522 (2)	C24—H24B	0.9600
C6—H6	0.9800	C24—H24C	0.9600
C7—H7A	0.9700	C25—C27	1.526 (2)
C7—H7B	0.9700	C25—C26	1.534 (2)
C8—H8A	0.9700	C25—C28	1.544 (2)
C8—H8B	0.9700	C26—H26A	0.9600
C11—C13	1.528 (2)	C26—H26B	0.9600
C11—C14	1.533 (2)	C26—H26C	0.9600
C11—C12	1.537 (2)	C27—H27A	0.9600
C12—H12A	0.9600	C27—H27B	0.9600
C12—H12B	0.9600	C27—H27C	0.9600
C12—H12C	0.9600	C28—H28A	0.9600
C13—H13A	0.9600	C28—H28B	0.9600
C13—H13B	0.9600	C28—H28C	0.9600
C13—H13C	0.9600

C1—Pd1—P2	83.84 (5)	C11—C13—H13C	109.5
C1—Pd1—P1	82.82 (5)	H13A—C13—H13C	109.5
P2—Pd1—P1	166.495 (15)	H13B—C13—H13C	109.5
C1—Pd1—Cl1	174.27 (5)	C11—C14—H14A	109.5
P2—Pd1—Cl1	96.201 (14)	C11—C14—H14B	109.5
P1—Pd1—Cl1	96.853 (14)	H14A—C14—H14B	109.5
C7—P1—C11	104.62 (7)	C11—C14—H14C	109.5
C7—P1—C15	104.21 (8)	H14A—C14—H14C	109.5
C11—P1—C15	112.70 (7)	H14B—C14—H14C	109.5
C7—P1—Pd1	103.48 (6)	C17—C15—C16	109.18 (14)
C11—P1—Pd1	116.43 (5)	C17—C15—C18	108.71 (14)
C15—P1—Pd1	113.65 (5)	C16—C15—C18	108.39 (14)
C8—P2—C21	105.91 (8)	C17—C15—P1	110.59 (11)
C8—P2—C25	104.13 (8)	C16—C15—P1	114.69 (12)
C21—P2—C25	111.83 (8)	C18—C15—P1	105.05 (11)
C8—P2—Pd1	102.38 (6)	C15—C16—H16A	109.5
C21—P2—Pd1	117.07 (5)	C15—C16—H16B	109.5
C25—P2—Pd1	113.80 (5)	H16A—C16—H16B	109.5
C2—C1—C6	110.78 (14)	C15—C16—H16C	109.5
C2—C1—Pd1	114.66 (11)	H16A—C16—H16C	109.5
C6—C1—Pd1	114.96 (11)	H16B—C16—H16C	109.5
C2—C1—H1	105.1	C15—C17—H17A	109.5
C6—C1—H1	105.1	C15—C17—H17B	109.5
Pd1—C1—H1	105.1	H17A—C17—H17B	109.5
C7—C2—C3	111.48 (13)	C15—C17—H17C	109.5
C7—C2—C1	110.69 (13)	H17A—C17—H17C	109.5
C3—C2—C1	112.39 (14)	H17B—C17—H17C	109.5
C7—C2—H2	107.3	C15—C18—H18A	109.5
C3—C2—H2	107.3	C15—C18—H18B	109.5
C1—C2—H2	107.3	H18A—C18—H18B	109.5
C4—C3—C2	112.57 (14)	C15—C18—H18C	109.5
C4—C3—H3A	109.1	H18A—C18—H18C	109.5
C2—C3—H3A	109.1	H18B—C18—H18C	109.5
C4—C3—H3B	109.1	C24—C21—C23	109.83 (14)
C2—C3—H3B	109.1	C24—C21—C22	107.91 (14)
H3A—C3—H3B	107.8	C23—C21—C22	108.62 (15)
C3—C4—C5	110.85 (14)	C24—C21—P2	110.58 (11)
C3—C4—H4A	109.5	C23—C21—P2	113.75 (12)
C5—C4—H4A	109.5	C22—C21—P2	105.90 (11)
C3—C4—H4B	109.5	C21—C22—H22A	109.5
C5—C4—H4B	109.5	C21—C22—H22B	109.5
H4A—C4—H4B	108.1	H22A—C22—H22B	109.5
C4—C5—C6	111.11 (14)	C21—C22—H22C	109.5
C4—C5—H5A	109.4	H22A—C22—H22C	109.5
C6—C5—H5A	109.4	H22B—C22—H22C	109.5
C4—C5—H5B	109.4	C21—C23—H23A	109.5
C6—C5—H5B	109.4	C21—C23—H23B	109.5
H5A—C5—H5B	108.0	H23A—C23—H23B	109.5
C8—C6—C5	112.41 (14)	C21—C23—H23C	109.5
C8—C6—C1	110.62 (14)	H23A—C23—H23C	109.5
C5—C6—C1	111.44 (14)	H23B—C23—H23C	109.5
C8—C6—H6	107.4	C21—C24—H24A	109.5
C5—C6—H6	107.4	C21—C24—H24B	109.5
C1—C6—H6	107.4	H24A—C24—H24B	109.5
C2—C7—P1	109.10 (11)	C21—C24—H24C	109.5
C2—C7—H7A	109.9	H24A—C24—H24C	109.5
P1—C7—H7A	109.9	H24B—C24—H24C	109.5
C2—C7—H7B	109.9	C27—C25—C26	109.96 (15)
P1—C7—H7B	109.9	C27—C25—C28	108.08 (14)
H7A—C7—H7B	108.3	C26—C25—C28	108.45 (14)
C6—C8—P2	108.99 (11)	C27—C25—P2	110.88 (12)
C6—C8—H8A	109.9	C26—C25—P2	113.98 (12)
P2—C8—H8A	109.9	C28—C25—P2	105.21 (11)
C6—C8—H8B	109.9	C25—C26—H26A	109.5
P2—C8—H8B	109.9	C25—C26—H26B	109.5
H8A—C8—H8B	108.3	H26A—C26—H26B	109.5
C13—C11—C14	109.63 (14)	C25—C26—H26C	109.5
C13—C11—C12	108.94 (14)	H26A—C26—H26C	109.5
C14—C11—C12	107.99 (14)	H26B—C26—H26C	109.5
C13—C11—P1	113.85 (12)	C25—C27—H27A	109.5
C14—C11—P1	110.77 (11)	C25—C27—H27B	109.5
C12—C11—P1	105.41 (11)	H27A—C27—H27B	109.5
C11—C12—H12A	109.5	C25—C27—H27C	109.5
C11—C12—H12B	109.5	H27A—C27—H27C	109.5
H12A—C12—H12B	109.5	H27B—C27—H27C	109.5
C11—C12—H12C	109.5	C25—C28—H28A	109.5
H12A—C12—H12C	109.5	C25—C28—H28B	109.5
H12B—C12—H12C	109.5	H28A—C28—H28B	109.5
C11—C13—H13A	109.5	C25—C28—H28C	109.5
C11—C13—H13B	109.5	H28A—C28—H28C	109.5
H13A—C13—H13B	109.5	H28B—C28—H28C	109.5

Experimental details

Crystal data
Chemical formula	[Pd(C₂₄H₄₉P₂)Cl]
M_r	541.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.9467 (2), 14.6159 (2), 15.5190 (3)
β (°)	100.339 (2)
V (Å³)	2665.80 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.15 × 0.10 × 0.05

Data collection
Diffractometer	Oxford Diffraction XCalibur 3 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.941, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	26794, 9297, 6699
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.767

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.070, 0.96
No. of reflections	9297
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.28, −0.56

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalMaker (CrystalMaker, 2011).

Acknowledgements

Financial support from the Swedish Research Council and the Knut and Alice Wallenberg Foundation is gratefully acknowledged. We also thank the Crafoord foundation for a post-doctoral grant to JMJvR.

References

Arunachalampillai, A., Olsson, D. & Wendt, O. F. (2009). Dalton Trans. pp. 8626–8630. Web of Science CSD CrossRef Google Scholar
Castonguay, A., Sui-Seng, C., Zargarian, D. & Beauchamp, A. L. (2006). Organometallics, 25, 602–608. Web of Science CSD CrossRef CAS Google Scholar
CrystalMaker (2011). CrystalMaker. CrystalMaker Software Ltd, Oxfordshire, England. URL: www.CrystalMaker.com. Google Scholar
Jonasson, K. J., Ahlsten, N. & Wendt, O. F. (2011). Inorg. Chim. Acta, 379, 76–80. Web of Science CSD CrossRef CAS Google Scholar
Kuznetsov, V. F., Lough, A. J. & Gusev, D. G. (2006). Inorg. Chim. Acta, 359, 2806–2811. Web of Science CSD CrossRef CAS Google Scholar
Nilsson, P. & Wendt, O. F. (2005). J. Organomet. Chem. 690, 4197–4202. Web of Science CrossRef CAS Google Scholar
Ohff, M., Ohff, A., van der Boom, M. E. & Milstein, D. (1997). J. Am. Chem. Soc. 119, 11687–11688. CSD CrossRef CAS Web of Science Google Scholar
Olsson, D., Arunachalampillai, A. & Wendt, O. F. (2007a). Dalton Trans. pp. 5427–5433. Web of Science CSD CrossRef Google Scholar
Olsson, D., Janse van Rensburg, J. M. & Wendt, O. F. (2007b). Acta Cryst. E63, m1969. Web of Science CSD CrossRef IUCr Journals Google Scholar
Olsson, D. & Wendt, O. F. (2009). J. Organomet. Chem. 694, 3112–3115. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Pandarus, V. & Zargarian, D. (2007). Chem. Commun. pp. 978–980. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sjövall, S., Wendt, O. F. & Andersson, C. (2002). J. Chem. Soc. Dalton Trans. pp. 1396–1400. Google Scholar

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