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

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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812047022/wm2700sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812047022/wm2700Isup2.hkl Contains datablock I

CCDC reference: 914225

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.028
wR factor = 0.070
Data-to-parameter ratio = 36.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.28
PLAT230_ALERT_2_C Hirshfeld Test Diff for    P1     --  C7      ..        5.9 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     --  C5      ..        5.5 su
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         26
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pd1    --  Cl1     ..       10.0 su
PLAT793_ALERT_4_G The Model has Chirality at C2      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C6      (Verify) ....          S
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        764

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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).

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

Supporting information

Key indicators

checkCIF/PLATON results

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