trans-Dichloridobis[dicyclo-hex-yl(2,4,6-trimethyl-phen-yl)phosphane-κP]palladium(II).

The title compound, [PdCl(2)(C(21)H(33)P)(2)], forms a monomeric complex with a trans-square-planar coordination geometry about the Pd(II) atom which lies on an inversion centre. The Pd-P bond lengths are 2.3760 (13) Å, while the Pd-Cl bond lengths are 2.3172 (14) Å. The observed structure was found to be closely related to that of trans-dichloridobis[dicyclo-hex-yl(phen-yl)phosphane-κP]palladium(II), [PdCl(2){P(C(6)H(11))(2)(C(6)H(5))}(2)] [Burgoyne et al. (2012 ▶). Acta Cryst. E68, m404].

Related literature

For a review on related compounds, see: Spessard & Miessler (1996 ▶). For the synthesis of the starting materials, see: Drew & Doyle (1990 ▶). For similar R—P2PdCl2 compounds, see: Ogutu & Meijboom (2011 ▶); Muller & Meijboom (2010a ▶,b ▶). For their applications, see: Bedford et al. (2004 ▶). For the closely related structure of trans-dichloridobis[dicyclo­hex­yl(phen­yl)phos­phane-κP]palladium(II), see: Burgoyne et al. (2012 ▶). For isotypic structures, see: Clarke et al. (2003 ▶); Grushin et al. (1994 ▶); Vuoti et al. (2008 ▶).

Experimental

Crystal data

[PdCl2(C21H33P)2]

M = 810.19

Triclinic,

a = 9.466 (5) Å

b = 10.625 (5) Å

c = 11.527 (5) Å

α = 63.932 (5)°

β = 84.500 (5)°

γ = 75.874 (5)°

V = 1009.8 (8) Å3

Z = 1

Mo Kα radiation

μ = 0.70 mm−1

T = 100 K

0.22 × 0.17 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007) T min = 0.861, T max = 0.896

17391 measured reflections

4932 independent reflections

3385 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.165

S = 1.02

4932 reflections

217 parameters

H-atom parameters constrained

Δρmax = 1.05 e Å−3

Δρmin = −1.93 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040810/zj2095sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040810/zj2095Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C42H66Cl2P2Pd	Z = 1
Mr = 810.19	F(000) = 428
Triclinic, P1	Dx = 1.332 Mg m−3Dm = 1.332 Mg m−3Dm measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.466 (5) Å	Cell parameters from 3294 reflections
b = 10.625 (5) Å	θ = 2.2–28.3°
c = 11.527 (5) Å	µ = 0.70 mm−1
α = 63.932 (5)°	T = 100 K
β = 84.500 (5)°	Cube, yellow
γ = 75.874 (5)°	0.22 × 0.17 × 0.16 mm
V = 1009.8 (8) Å3

Bruker APEXII CCD diffractometer	3385 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.861, Tmax = 0.896	k = −14→14
17391 measured reflections	l = −15→15
4932 independent reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0919P)2] where P = (Fo2 + 2Fc2)/3
4932 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 1.05 e Å−3
0 restraints	Δρmin = −1.93 e Å−3

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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Pd1	0.5	0	0.5	0.02770 (17)
Cl2	0.66664 (12)	0.13206 (13)	0.48974 (13)	0.0403 (3)
P1	0.31238 (11)	0.14874 (12)	0.56557 (10)	0.0279 (3)
C16	0.3797 (5)	0.2560 (5)	0.6307 (4)	0.0332 (10)
C11	0.1511 (6)	0.2214 (6)	0.3425 (5)	0.0420 (12)
H11A	0.0817	0.1659	0.4001	0.05*
H11B	0.2285	0.1549	0.3197	0.05*
C6	0.0268 (5)	0.1246 (5)	0.6872 (5)	0.0363 (11)
C2	0.2357 (5)	−0.0711 (5)	0.7937 (5)	0.0358 (11)
C1	0.1790 (5)	0.0641 (5)	0.6878 (4)	0.0316 (10)
H1	0.1609	0.0137	0.6369	0.038*
C4	−0.0041 (6)	−0.0812 (6)	0.8892 (5)	0.0438 (12)
C21	0.4639 (5)	0.1621 (6)	0.7596 (5)	0.0405 (12)
H21A	0.3976	0.1123	0.8265	0.049*
H21B	0.5438	0.0881	0.7492	0.049*
C17	0.2603 (5)	0.3749 (5)	0.6446 (5)	0.0415 (12)
H17A	0.2087	0.4373	0.5608	0.05*
H17B	0.1885	0.3314	0.7089	0.05*
C15	0.3216 (5)	0.3781 (6)	0.3220 (5)	0.0435 (12)
H15A	0.3587	0.4253	0.3663	0.052*
H15B	0.406	0.3152	0.3018	0.052*
C3	0.1420 (6)	−0.1368 (5)	0.8900 (5)	0.0427 (12)
H3	0.1822	−0.2255	0.9604	0.051*
C12	0.0713 (6)	0.3418 (6)	0.2195 (5)	0.0501 (14)
H12A	0.028	0.2989	0.1747	0.06*
H12B	−0.009	0.4051	0.2434	0.06*
C7	0.3943 (6)	−0.1527 (6)	0.8096 (5)	0.0491 (14)
H7A	0.4314	−0.173	0.894	0.074*
H7B	0.4521	−0.0943	0.7411	0.074*
H7C	0.4014	−0.2434	0.8039	0.074*
C10	0.2180 (5)	0.2864 (5)	0.4122 (4)	0.0300 (9)
H10	0.1369	0.3521	0.4343	0.036*
C18	0.3265 (6)	0.4651 (6)	0.6878 (7)	0.0567 (16)
H18A	0.3939	0.5129	0.6208	0.068*
H18B	0.248	0.5408	0.6971	0.068*
C20	0.5269 (6)	0.2537 (7)	0.8028 (6)	0.0527 (14)
H20A	0.5996	0.2965	0.7393	0.063*
H20B	0.5774	0.1917	0.8871	0.063*
C9	−0.0548 (5)	0.2671 (6)	0.5890 (5)	0.0477 (13)
H9A	−0.155	0.2882	0.6177	0.071*
H9B	−0.056	0.2633	0.5057	0.071*
H9C	−0.0064	0.3428	0.5796	0.071*
C13	0.1717 (7)	0.4301 (6)	0.1292 (5)	0.0555 (15)
H13A	0.1159	0.5087	0.0527	0.067*
H13B	0.2475	0.3689	0.0991	0.067*
C5	−0.0587 (5)	0.0501 (6)	0.7852 (5)	0.0449 (13)
H5	−0.1604	0.0906	0.7816	0.054*
C19	0.4088 (6)	0.3735 (7)	0.8154 (6)	0.0565 (15)
H19A	0.3405	0.3313	0.8844	0.068*
H19B	0.4537	0.434	0.8392	0.068*
C14	0.2432 (6)	0.4931 (6)	0.1962 (5)	0.0517 (14)
H14A	0.1681	0.564	0.2157	0.062*
H14B	0.3144	0.5446	0.1373	0.062*
C8	−0.1042 (7)	−0.1536 (7)	0.9946 (6)	0.0652 (18)
H8A	−0.0615	−0.257	1.038	0.098*
H8B	−0.199	−0.1378	0.9569	0.098*
H8C	−0.1171	−0.1129	1.0575	0.098*

	U11	U22	U33	U12	U13	U23
Pd1	0.0255 (3)	0.0175 (3)	0.0286 (3)	0.00253 (18)	0.00010 (18)	−0.00339 (19)
Cl2	0.0323 (6)	0.0314 (6)	0.0560 (8)	−0.0062 (5)	0.0050 (5)	−0.0190 (6)
P1	0.0264 (6)	0.0194 (6)	0.0277 (6)	0.0018 (4)	−0.0007 (4)	−0.0043 (5)
C16	0.034 (2)	0.027 (2)	0.034 (2)	0.0008 (19)	−0.0038 (19)	−0.011 (2)
C11	0.042 (3)	0.035 (3)	0.041 (3)	−0.001 (2)	−0.007 (2)	−0.013 (2)
C6	0.032 (2)	0.032 (3)	0.042 (3)	−0.002 (2)	0.003 (2)	−0.017 (2)
C2	0.037 (2)	0.026 (2)	0.034 (2)	0.0014 (19)	0.0014 (19)	−0.007 (2)
C1	0.036 (2)	0.021 (2)	0.029 (2)	0.0017 (18)	−0.0018 (18)	−0.0067 (18)
C4	0.051 (3)	0.038 (3)	0.046 (3)	−0.021 (2)	0.016 (2)	−0.019 (2)
C21	0.038 (3)	0.037 (3)	0.035 (3)	0.002 (2)	−0.004 (2)	−0.009 (2)
C17	0.035 (2)	0.032 (3)	0.054 (3)	0.001 (2)	−0.002 (2)	−0.020 (2)
C15	0.042 (3)	0.035 (3)	0.031 (2)	−0.003 (2)	−0.003 (2)	0.004 (2)
C3	0.055 (3)	0.030 (3)	0.030 (2)	−0.007 (2)	0.008 (2)	−0.005 (2)
C12	0.051 (3)	0.049 (3)	0.044 (3)	−0.004 (3)	−0.016 (2)	−0.014 (3)
C7	0.049 (3)	0.030 (3)	0.040 (3)	0.013 (2)	0.005 (2)	−0.002 (2)
C10	0.027 (2)	0.024 (2)	0.027 (2)	0.0038 (17)	−0.0026 (17)	−0.0049 (18)
C18	0.046 (3)	0.044 (3)	0.088 (5)	−0.003 (3)	0.004 (3)	−0.040 (3)
C20	0.045 (3)	0.061 (4)	0.051 (3)	−0.001 (3)	−0.008 (3)	−0.028 (3)
C9	0.029 (2)	0.045 (3)	0.047 (3)	0.006 (2)	0.003 (2)	−0.009 (3)
C13	0.065 (4)	0.048 (3)	0.035 (3)	0.002 (3)	−0.013 (3)	−0.006 (3)
C5	0.029 (2)	0.047 (3)	0.057 (3)	−0.008 (2)	0.008 (2)	−0.023 (3)
C19	0.052 (3)	0.069 (4)	0.065 (4)	−0.016 (3)	0.015 (3)	−0.045 (4)
C14	0.051 (3)	0.039 (3)	0.038 (3)	−0.006 (3)	−0.012 (2)	0.007 (2)
C8	0.075 (4)	0.056 (4)	0.062 (4)	−0.024 (3)	0.032 (3)	−0.024 (3)

Pd1—Cl2	2.3172 (14)	C15—H15A	0.99
Pd1—Cl2i	2.3172 (14)	C15—H15B	0.99
Pd1—P1	2.3760 (13)	C3—H3	0.95
Pd1—P1i	2.3760 (13)	C12—C13	1.502 (8)
P1—C10	1.859 (4)	C12—H12A	0.99
P1—C16	1.862 (5)	C12—H12B	0.99
P1—C1	1.868 (5)	C7—H7A	0.98
C16—C17	1.532 (6)	C7—H7B	0.98
C16—C21	1.541 (6)	C7—H7C	0.98
C11—C10	1.524 (7)	C10—H10	1
C11—C12	1.536 (7)	C18—C19	1.520 (9)
C11—H11A	0.99	C18—H18A	0.99
C11—H11B	0.99	C18—H18B	0.99
C6—C5	1.382 (7)	C20—C19	1.526 (8)
C6—C1	1.427 (6)	C20—H20A	0.99
C6—C9	1.503 (7)	C20—H20B	0.99
C2—C3	1.393 (6)	C9—H9A	0.98
C2—C1	1.431 (6)	C9—H9B	0.98
C2—C7	1.522 (6)	C9—H9C	0.98
C1—H1	1	C13—C14	1.509 (8)
C4—C3	1.364 (7)	C13—H13A	0.99
C4—C5	1.395 (8)	C13—H13B	0.99
C4—C8	1.510 (7)	C5—H5	0.95
C21—C20	1.522 (8)	C19—H19A	0.99
C21—H21A	0.99	C19—H19B	0.99
C21—H21B	0.99	C14—H14A	0.99
C17—C18	1.526 (7)	C14—H14B	0.99
C17—H17A	0.99	C8—H8A	0.98
C17—H17B	0.99	C8—H8B	0.98
C15—C14	1.534 (6)	C8—H8C	0.98
C15—C10	1.540 (6)
Cl2—Pd1—Cl2i	180	C13—C12—H12B	109.2
Cl2—Pd1—P1	91.61 (6)	C11—C12—H12B	109.2
Cl2i—Pd1—P1	88.39 (6)	H12A—C12—H12B	107.9
Cl2—Pd1—P1i	88.39 (6)	C2—C7—H7A	109.5
Cl2i—Pd1—P1i	91.61 (6)	C2—C7—H7B	109.5
P1—Pd1—P1i	180	H7A—C7—H7B	109.5
C10—P1—C16	103.8 (2)	C2—C7—H7C	109.5
C10—P1—C1	110.9 (2)	H7A—C7—H7C	109.5
C16—P1—C1	104.3 (2)	H7B—C7—H7C	109.5
C10—P1—Pd1	104.11 (15)	C11—C10—C15	110.4 (4)
C16—P1—Pd1	114.10 (15)	C11—C10—P1	112.8 (3)
C1—P1—Pd1	118.79 (15)	C15—C10—P1	110.9 (3)
C17—C16—C21	109.7 (4)	C11—C10—H10	107.5
C17—C16—P1	113.7 (3)	C15—C10—H10	107.5
C21—C16—P1	112.9 (3)	P1—C10—H10	107.5
C10—C11—C12	109.6 (4)	C19—C18—C17	111.6 (5)
C10—C11—H11A	109.7	C19—C18—H18A	109.3
C12—C11—H11A	109.7	C17—C18—H18A	109.3
C10—C11—H11B	109.7	C19—C18—H18B	109.3
C12—C11—H11B	109.7	C17—C18—H18B	109.3
H11A—C11—H11B	108.2	H18A—C18—H18B	108
C5—C6—C1	119.4 (4)	C21—C20—C19	111.7 (5)
C5—C6—C9	114.2 (4)	C21—C20—H20A	109.3
C1—C6—C9	126.4 (4)	C19—C20—H20A	109.3
C3—C2—C1	119.4 (4)	C21—C20—H20B	109.3
C3—C2—C7	115.9 (4)	C19—C20—H20B	109.3
C1—C2—C7	124.7 (4)	H20A—C20—H20B	107.9
C6—C1—C2	117.3 (4)	C6—C9—H9A	109.5
C6—C1—P1	125.7 (3)	C6—C9—H9B	109.5
C2—C1—P1	116.9 (3)	H9A—C9—H9B	109.5
C6—C1—H1	90.7	C6—C9—H9C	109.5
C2—C1—H1	90.7	H9A—C9—H9C	109.5
P1—C1—H1	90.7	H9B—C9—H9C	109.5
C3—C4—C5	116.5 (4)	C12—C13—C14	110.5 (5)
C3—C4—C8	123.1 (5)	C12—C13—H13A	109.6
C5—C4—C8	120.4 (5)	C14—C13—H13A	109.6
C20—C21—C16	110.7 (4)	C12—C13—H13B	109.6
C20—C21—H21A	109.5	C14—C13—H13B	109.6
C16—C21—H21A	109.5	H13A—C13—H13B	108.1
C20—C21—H21B	109.5	C6—C5—C4	123.7 (5)
C16—C21—H21B	109.5	C6—C5—H5	118.2
H21A—C21—H21B	108.1	C4—C5—H5	118.2
C18—C17—C16	110.3 (4)	C18—C19—C20	109.5 (5)
C18—C17—H17A	109.6	C18—C19—H19A	109.8
C16—C17—H17A	109.6	C20—C19—H19A	109.8
C18—C17—H17B	109.6	C18—C19—H19B	109.8
C16—C17—H17B	109.6	C20—C19—H19B	109.8
H17A—C17—H17B	108.1	H19A—C19—H19B	108.2
C14—C15—C10	110.9 (4)	C13—C14—C15	112.5 (5)
C14—C15—H15A	109.4	C13—C14—H14A	109.1
C10—C15—H15A	109.4	C15—C14—H14A	109.1
C14—C15—H15B	109.4	C13—C14—H14B	109.1
C10—C15—H15B	109.4	C15—C14—H14B	109.1
H15A—C15—H15B	108	H14A—C14—H14B	107.8
C4—C3—C2	123.7 (5)	C4—C8—H8A	109.5
C4—C3—H3	118.1	C4—C8—H8B	109.5
C2—C3—H3	118.1	H8A—C8—H8B	109.5
C13—C12—C11	111.8 (5)	C4—C8—H8C	109.5
C13—C12—H12A	109.2	H8A—C8—H8C	109.5
C11—C12—H12A	109.2	H8B—C8—H8C	109.5