Bis[(1,1'-biphenyl-2,2'-di-yl)di-tert-butyl-phospho-nium] di-μ-chlorido-bis-[dichlorido-palladate(II)].

In the title compound, (C(20)H(26)P)(2)[Pd(2)Cl(6)], the Pd(II) atom within the hexachloridodipalladate(II) dianion has a square-planar geometry. It resides on a centre of inversion with the asymmetric unit containing half of the dianion and one phospho-nium cation. Only weak C-H⋯π inter-actions are present in the crystal structure.

Related literature

For the structures of related PdII complexes and background to organopalladium-catalysed reactions, see: Ormondi et al. (2011 ▶); Williams et al. (2008 ▶); Migowski & DuPont (2007 ▶); d′OrLyé & Jutland (2005 ▶); Beletskaya & Cheprakov (2004 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

(C20H26P)2[Pd2Cl6]

M = 1020.26

Triclinic,

a = 8.3247 (2) Å

b = 11.2697 (2) Å

c = 11.7004 (3) Å

α = 73.0982 (6)°

β = 85.0900 (6)°

γ = 82.2708 (5)°

V = 1039.49 (4) Å3

Z = 1

Mo Kα radiation

μ = 1.36 mm−1

T = 100 K

0.29 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (AXScale; Bruker, 2010 ▶) T min = 0.695, T max = 0.774

39747 measured reflections

5184 independent reflections

5088 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.015

wR(F 2) = 0.037

S = 1.05

5184 reflections

232 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037786/gg2094sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037786/gg2094Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037786/gg2094Isup3.mol

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

(C20H26P)2[Pd2Cl6]	Z = 1
Mr = 1020.26	F(000) = 516
Triclinic, P1	Dx = 1.630 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3247 (2) Å	Cell parameters from 9253 reflections
b = 11.2697 (2) Å	θ = 3.6–28.4°
c = 11.7004 (3) Å	µ = 1.36 mm−1
α = 73.0982 (6)°	T = 100 K
β = 85.0900 (6)°	Prism, dark orange
γ = 82.2708 (5)°	0.29 × 0.22 × 0.20 mm
V = 1039.49 (4) Å3

Bruker APEXII CCD diffractometer	5184 independent reflections
Radiation source: fine-focus sealed tube	5088 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 28.5°, θmin = 2.9°
Absorption correction: multi-scan (AXScale; Bruker, 2010)	h = −11→11
Tmin = 0.695, Tmax = 0.774	k = −15→15
39747 measured reflections	l = −15→15

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)] = 0.015	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.037	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0139P)2 + 0.6282P] where P = (Fo2 + 2Fc2)/3
5184 reflections	(Δ/σ)max = 0.002
232 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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.

	x	y	z	Uiso*/Ueq
C16	0.06541 (14)	0.17413 (10)	0.35252 (11)	0.0171 (2)
H16A	0.1167	0.1453	0.4297	0.026*
H16B	0.1288	0.1356	0.2953	0.026*
H16C	−0.0451	0.1504	0.3628	0.026*
C2	0.51131 (13)	0.18374 (10)	0.38452 (10)	0.0150 (2)
C6	0.36510 (14)	0.28059 (11)	0.52998 (11)	0.0182 (2)
H6	0.2787	0.3363	0.5501	0.022*
C1	0.38564 (13)	0.26782 (10)	0.41465 (10)	0.0147 (2)
C3	0.61953 (14)	0.11512 (11)	0.47087 (11)	0.0186 (2)
H3	0.7057	0.0588	0.4515	0.022*
C5	0.47340 (15)	0.21017 (12)	0.61544 (11)	0.0213 (2)
H5	0.4601	0.2173	0.6947	0.026*
C4	0.60052 (15)	0.12966 (12)	0.58561 (11)	0.0215 (2)
H4	0.6753	0.0840	0.6441	0.026*
C17	0.32342 (14)	0.50983 (10)	0.22795 (11)	0.0161 (2)
C13	0.05899 (13)	0.31677 (10)	0.30507 (10)	0.0137 (2)
C7	0.51087 (13)	0.17674 (10)	0.26061 (10)	0.0149 (2)
C19	0.25132 (15)	0.58473 (11)	0.31437 (12)	0.0215 (2)
H19A	0.2870	0.5412	0.3951	0.032*
H19B	0.1326	0.5930	0.3149	0.032*
H19C	0.2883	0.6678	0.2884	0.032*
C18	0.26103 (15)	0.57096 (11)	0.10206 (11)	0.0211 (2)
H18A	0.1421	0.5790	0.1061	0.032*
H18B	0.3034	0.5190	0.0496	0.032*
H18C	0.2977	0.6539	0.0701	0.032*
C15	−0.03314 (14)	0.37709 (11)	0.39742 (11)	0.0181 (2)
H15A	−0.0455	0.4681	0.3642	0.027*
H15B	0.0279	0.3537	0.4702	0.027*
H15C	−0.1406	0.3479	0.4167	0.027*
C12	0.61554 (14)	0.09816 (11)	0.20828 (11)	0.0190 (2)
H12	0.7014	0.0445	0.2517	0.023*
C14	−0.02701 (14)	0.36283 (11)	0.18602 (11)	0.0180 (2)
H14A	0.0365	0.3286	0.1260	0.027*
H14B	−0.0369	0.4542	0.1584	0.027*
H14C	−0.1353	0.3350	0.1979	0.027*
C20	0.50976 (14)	0.50237 (12)	0.22269 (13)	0.0228 (2)
H20A	0.5562	0.4503	0.1713	0.034*
H20B	0.5491	0.4656	0.3034	0.034*
H20C	0.5426	0.5865	0.1900	0.034*
C9	0.36534 (14)	0.25847 (10)	0.07624 (10)	0.0157 (2)
H9	0.2817	0.3136	0.0314	0.019*
C8	0.38668 (13)	0.25742 (10)	0.19316 (10)	0.0137 (2)
C10	0.46880 (14)	0.17729 (11)	0.02614 (11)	0.0183 (2)
H10	0.4545	0.1754	−0.0530	0.022*
C11	0.59299 (15)	0.09897 (11)	0.09144 (12)	0.0205 (2)
H11	0.6639	0.0449	0.0557	0.025*
Cl3	0.06462 (4)	0.07944 (3)	1.07304 (2)	0.01962 (6)
Cl2	0.15259 (3)	0.29365 (2)	0.81900 (2)	0.01663 (5)
Cl1	0.01589 (3)	0.12552 (3)	0.67310 (2)	0.01763 (6)
P1	0.27397 (3)	0.34725 (3)	0.28353 (2)	0.01179 (5)
Pd1	0.041384 (9)	0.110164 (7)	0.868729 (7)	0.01193 (3)

	U11	U22	U33	U12	U13	U23
C16	0.0169 (5)	0.0132 (5)	0.0208 (5)	−0.0040 (4)	0.0012 (4)	−0.0037 (4)
C2	0.0129 (5)	0.0132 (5)	0.0177 (5)	−0.0035 (4)	−0.0001 (4)	−0.0018 (4)
C6	0.0177 (5)	0.0209 (6)	0.0170 (5)	−0.0038 (4)	−0.0011 (4)	−0.0060 (4)
C1	0.0135 (5)	0.0149 (5)	0.0151 (5)	−0.0025 (4)	−0.0017 (4)	−0.0025 (4)
C3	0.0134 (5)	0.0170 (5)	0.0230 (6)	−0.0027 (4)	−0.0025 (4)	−0.0010 (4)
C5	0.0214 (6)	0.0260 (6)	0.0173 (5)	−0.0072 (5)	−0.0036 (4)	−0.0046 (5)
C4	0.0180 (5)	0.0228 (6)	0.0213 (6)	−0.0059 (4)	−0.0071 (4)	0.0009 (5)
C17	0.0149 (5)	0.0123 (5)	0.0208 (5)	−0.0032 (4)	0.0008 (4)	−0.0042 (4)
C13	0.0118 (5)	0.0128 (5)	0.0162 (5)	−0.0021 (4)	0.0006 (4)	−0.0037 (4)
C7	0.0127 (5)	0.0126 (5)	0.0181 (5)	−0.0020 (4)	0.0003 (4)	−0.0026 (4)
C19	0.0229 (6)	0.0161 (5)	0.0280 (6)	−0.0024 (4)	−0.0005 (5)	−0.0103 (5)
C18	0.0236 (6)	0.0157 (5)	0.0210 (6)	−0.0038 (4)	0.0000 (5)	−0.0001 (4)
C15	0.0161 (5)	0.0174 (5)	0.0204 (6)	−0.0012 (4)	0.0035 (4)	−0.0064 (4)
C12	0.0152 (5)	0.0159 (5)	0.0242 (6)	0.0015 (4)	0.0009 (4)	−0.0049 (5)
C14	0.0151 (5)	0.0192 (5)	0.0193 (5)	−0.0013 (4)	−0.0033 (4)	−0.0043 (4)
C20	0.0151 (5)	0.0189 (6)	0.0337 (7)	−0.0055 (4)	0.0013 (5)	−0.0052 (5)
C9	0.0152 (5)	0.0149 (5)	0.0169 (5)	−0.0023 (4)	0.0007 (4)	−0.0043 (4)
C8	0.0127 (5)	0.0117 (5)	0.0163 (5)	−0.0015 (4)	0.0014 (4)	−0.0039 (4)
C10	0.0193 (5)	0.0188 (5)	0.0184 (5)	−0.0039 (4)	0.0034 (4)	−0.0082 (4)
C11	0.0187 (5)	0.0173 (5)	0.0255 (6)	−0.0001 (4)	0.0045 (4)	−0.0088 (5)
Cl3	0.03037 (15)	0.01788 (13)	0.01368 (12)	−0.01237 (11)	0.00371 (10)	−0.00635 (10)
Cl2	0.01830 (12)	0.01205 (11)	0.01884 (13)	−0.00401 (9)	−0.00206 (10)	−0.00193 (10)
Cl1	0.02204 (13)	0.01686 (12)	0.01351 (12)	−0.00352 (10)	−0.00294 (9)	−0.00237 (10)
P1	0.01112 (12)	0.01095 (12)	0.01294 (12)	−0.00073 (9)	−0.00015 (9)	−0.00320 (10)
Pd1	0.01306 (4)	0.01056 (4)	0.01228 (4)	−0.00235 (3)	0.00107 (3)	−0.00344 (3)

C16—C13	1.5356 (15)	C19—H19C	0.9800
C16—H16A	0.9800	C18—H18A	0.9800
C16—H16B	0.9800	C18—H18B	0.9800
C16—H16C	0.9800	C18—H18C	0.9800
C2—C3	1.3945 (15)	C15—H15A	0.9800
C2—C1	1.4075 (15)	C15—H15B	0.9800
C2—C7	1.4751 (16)	C15—H15C	0.9800
C6—C1	1.3920 (16)	C12—C11	1.3930 (18)
C6—C5	1.3939 (16)	C12—H12	0.9500
C6—H6	0.9500	C14—H14A	0.9800
C1—P1	1.8003 (11)	C14—H14B	0.9800
C3—C4	1.3924 (18)	C14—H14C	0.9800
C3—H3	0.9500	C20—H20A	0.9800
C5—C4	1.3884 (18)	C20—H20B	0.9800
C5—H5	0.9500	C20—H20C	0.9800
C4—H4	0.9500	C9—C8	1.3911 (16)
C17—C19	1.5335 (16)	C9—C10	1.3913 (16)
C17—C18	1.5357 (17)	C9—H9	0.9500
C17—C20	1.5391 (16)	C8—P1	1.7945 (11)
C17—P1	1.8476 (11)	C10—C11	1.3890 (17)
C13—C15	1.5371 (15)	C10—H10	0.9500
C13—C14	1.5404 (15)	C11—H11	0.9500
C13—P1	1.8500 (11)	Cl3—Pd1i	2.3166 (3)
C7—C12	1.3908 (16)	Cl3—Pd1	2.3349 (3)
C7—C8	1.4100 (15)	Cl2—Pd1	2.2791 (3)
C19—H19A	0.9800	Cl1—Pd1	2.2709 (3)
C19—H19B	0.9800	Pd1—Cl3i	2.3166 (3)
C13—C16—H16A	109.5	H18A—C18—H18C	109.5
C13—C16—H16B	109.5	H18B—C18—H18C	109.5
H16A—C16—H16B	109.5	C13—C15—H15A	109.5
C13—C16—H16C	109.5	C13—C15—H15B	109.5
H16A—C16—H16C	109.5	H15A—C15—H15B	109.5
H16B—C16—H16C	109.5	C13—C15—H15C	109.5
C3—C2—C1	119.27 (11)	H15A—C15—H15C	109.5
C3—C2—C7	126.57 (11)	H15B—C15—H15C	109.5
C1—C2—C7	114.15 (10)	C7—C12—C11	119.26 (11)
C1—C6—C5	118.86 (11)	C7—C12—H12	120.4
C1—C6—H6	120.6	C11—C12—H12	120.4
C5—C6—H6	120.6	C13—C14—H14A	109.5
C6—C1—C2	121.02 (10)	C13—C14—H14B	109.5
C6—C1—P1	130.24 (9)	H14A—C14—H14B	109.5
C2—C1—P1	108.73 (8)	C13—C14—H14C	109.5
C4—C3—C2	119.62 (11)	H14A—C14—H14C	109.5
C4—C3—H3	120.2	H14B—C14—H14C	109.5
C2—C3—H3	120.2	C17—C20—H20A	109.5
C4—C5—C6	120.51 (12)	C17—C20—H20B	109.5
C4—C5—H5	119.7	H20A—C20—H20B	109.5
C6—C5—H5	119.7	C17—C20—H20C	109.5
C5—C4—C3	120.69 (11)	H20A—C20—H20C	109.5
C5—C4—H4	119.7	H20B—C20—H20C	109.5
C3—C4—H4	119.7	C8—C9—C10	118.76 (11)
C19—C17—C18	110.87 (10)	C8—C9—H9	120.6
C19—C17—C20	109.39 (10)	C10—C9—H9	120.6
C18—C17—C20	109.59 (10)	C9—C8—C7	121.31 (10)
C19—C17—P1	110.43 (8)	C9—C8—P1	129.83 (9)
C18—C17—P1	110.18 (8)	C7—C8—P1	108.86 (8)
C20—C17—P1	106.27 (8)	C11—C10—C9	120.21 (11)
C16—C13—C15	109.56 (9)	C11—C10—H10	119.9
C16—C13—C14	109.59 (9)	C9—C10—H10	119.9
C15—C13—C14	109.98 (9)	C10—C11—C12	121.24 (11)
C16—C13—P1	104.76 (7)	C10—C11—H11	119.4
C15—C13—P1	111.52 (8)	C12—C11—H11	119.4
C14—C13—P1	111.29 (8)	Pd1i—Cl3—Pd1	94.884 (10)
C12—C7—C8	119.19 (11)	C8—P1—C1	93.92 (5)
C12—C7—C2	126.66 (10)	C8—P1—C17	108.77 (5)
C8—C7—C2	114.12 (10)	C1—P1—C17	109.07 (5)
C17—C19—H19A	109.5	C8—P1—C13	110.90 (5)
C17—C19—H19B	109.5	C1—P1—C13	111.69 (5)
H19A—C19—H19B	109.5	C17—P1—C13	119.48 (5)
C17—C19—H19C	109.5	Cl1—Pd1—Cl2	91.333 (10)
H19A—C19—H19C	109.5	Cl1—Pd1—Cl3i	90.924 (10)
H19B—C19—H19C	109.5	Cl2—Pd1—Cl3i	177.377 (10)
C17—C18—H18A	109.5	Cl1—Pd1—Cl3	175.919 (10)
C17—C18—H18B	109.5	Cl2—Pd1—Cl3	92.603 (10)
H18A—C18—H18B	109.5	Cl3i—Pd1—Cl3	85.117 (10)
C17—C18—H18C	109.5
C5—C6—C1—C2	1.22 (17)	C7—C8—P1—C17	107.86 (8)
C5—C6—C1—P1	−177.59 (9)	C9—C8—P1—C13	60.63 (12)
C3—C2—C1—C6	−1.94 (17)	C7—C8—P1—C13	−118.81 (8)
C7—C2—C1—C6	176.93 (10)	C6—C1—P1—C8	−176.59 (11)
C3—C2—C1—P1	177.11 (9)	C2—C1—P1—C8	4.49 (9)
C7—C2—C1—P1	−4.03 (12)	C6—C1—P1—C17	72.01 (12)
C1—C2—C3—C4	0.77 (17)	C2—C1—P1—C17	−106.92 (8)
C7—C2—C3—C4	−177.94 (11)	C6—C1—P1—C13	−62.25 (12)
C1—C6—C5—C4	0.65 (18)	C2—C1—P1—C13	118.82 (8)
C6—C5—C4—C3	−1.81 (19)	C19—C17—P1—C8	−170.94 (8)
C2—C3—C4—C5	1.08 (18)	C18—C17—P1—C8	66.24 (9)
C3—C2—C7—C12	1.82 (19)	C20—C17—P1—C8	−52.40 (9)
C1—C2—C7—C12	−176.95 (11)	C19—C17—P1—C1	−69.77 (9)
C3—C2—C7—C8	−179.97 (11)	C18—C17—P1—C1	167.42 (8)
C1—C2—C7—C8	1.26 (14)	C20—C17—P1—C1	48.77 (9)
C8—C7—C12—C11	−1.44 (17)	C19—C17—P1—C13	60.37 (10)
C2—C7—C12—C11	176.69 (11)	C18—C17—P1—C13	−62.44 (10)
C10—C9—C8—C7	0.39 (16)	C20—C17—P1—C13	178.91 (8)
C10—C9—C8—P1	−178.98 (9)	C16—C13—P1—C8	52.91 (9)
C12—C7—C8—C9	1.04 (16)	C15—C13—P1—C8	171.33 (8)
C2—C7—C8—C9	−177.32 (10)	C14—C13—P1—C8	−65.44 (9)
C12—C7—C8—P1	−179.47 (9)	C16—C13—P1—C1	−50.42 (9)
C2—C7—C8—P1	2.18 (12)	C15—C13—P1—C1	68.00 (9)
C8—C9—C10—C11	−1.41 (17)	C14—C13—P1—C1	−168.77 (8)
C9—C10—C11—C12	1.01 (18)	C16—C13—P1—C17	−179.38 (7)
C7—C12—C11—C10	0.44 (18)	C15—C13—P1—C17	−60.96 (10)
C9—C8—P1—C1	175.63 (11)	C14—C13—P1—C17	62.27 (9)
C7—C8—P1—C1	−3.81 (8)	Pd1i—Cl3—Pd1—Cl2	−178.700 (11)
C9—C8—P1—C17	−72.71 (12)	Pd1i—Cl3—Pd1—Cl3i	0.0

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg7ii	0.95	2.68	3.5952 (13)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg7 is the centroid of the Pd1,Cl3,Pd1′,Cl3′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg7i	0.95	2.68	3.5952 (13)	138

Symmetry code: (i) .