trans-Dichloridobis[diphen-yl(4-vinyl-phen-yl)phosphane-κP]palladium(II).

In the title compound, [PdCl(2)(C(20)H(17)P)(2)], the Pd(II) atom lies on a center of symmetry, resulting in a distorted trans-square-planar geometry. The Pd-P and Pd-Cl bond lengths are 2.3366 (7) and 2.2966 (7) Å, respectively. The vinyl group is disordered over two sets of sites in a 0.696 (15):0.304 (15) ratio.

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 ▶).

Experimental

Crystal data

[PdCl2(C20H17P)2]

M = 753.91

Triclinic,

a = 9.9495 (3) Å

b = 9.9512 (3) Å

c = 10.4387 (4) Å

α = 67.683 (2)°

β = 86.366 (2)°

γ = 61.979 (2)°

V = 835.62 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.84 mm−1

T = 100 K

0.24 × 0.18 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.837, T max = 0.955

5829 measured reflections

2723 independent reflections

2682 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.105

S = 1.07

2723 reflections

205 parameters

H-atom parameters constrained

Δρmax = 1.66 e Å−3

Δρmin = −0.75 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044795/fi2114sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044795/fi2114Isup2.hkl

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

[PdCl2(C20H17P)2]	Z = 1
Mr = 753.91	F(000) = 384
Triclinic, P1	Dx = 1.498 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.9495 (3) Å	Cell parameters from 5189 reflections
b = 9.9512 (3) Å	θ = 4.6–64.1°
c = 10.4387 (4) Å	µ = 0.84 mm−1
α = 67.683 (2)°	T = 100 K
β = 86.366 (2)°	Plate, yellow
γ = 61.979 (2)°	0.24 × 0.18 × 0.06 mm
V = 835.62 (5) Å3

Bruker APEXII CCD diffractometer	2723 independent reflections
Radiation source: sealed tube	2682 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 24.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→8
Tmin = 0.837, Tmax = 0.955	k = −11→9
5829 measured reflections	l = −11→12

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0461P)2 + 2.1233P] where P = (Fo2 + 2Fc2)/3
2723 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 1.66 e Å−3
0 restraints	Δρmin = −0.75 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	Occ. (<1)
C11	0.8766 (3)	0.2614 (4)	0.6548 (3)	0.0283 (6)
C12	0.8919 (4)	0.1305 (4)	0.6246 (3)	0.0364 (7)
H12	0.96	0.0217	0.683	0.044*
C13	0.8047 (4)	0.1631 (5)	0.5062 (4)	0.0441 (9)
H13	0.8175	0.0753	0.4853	0.053*
C14	0.6994 (4)	0.3238 (5)	0.4194 (3)	0.0468 (9)
C15	0.6826 (4)	0.4504 (5)	0.4536 (3)	0.0459 (9)
H15	0.6107	0.5589	0.3981	0.055*
C16	0.7708 (4)	0.4203 (4)	0.5696 (3)	0.0355 (7)
H16	0.7579	0.5087	0.5897	0.043*
C17	0.5932 (8)	0.3815 (11)	0.2904 (8)	0.0354 (17)	0.696 (15)
H17	0.5121	0.4896	0.2551	0.042*	0.696 (15)
C18	0.6107 (6)	0.2857 (8)	0.2271 (6)	0.046 (2)	0.696 (15)
H18A	0.6911	0.1771	0.2609	0.056*	0.696 (15)
H18B	0.543	0.3255	0.148	0.056*	0.696 (15)
C19	0.6584 (19)	0.292 (2)	0.3018 (15)	0.034 (4)	0.304 (15)
H19	0.6993	0.1868	0.3024	0.04*	0.304 (15)
C20	0.5616 (16)	0.424 (2)	0.200 (2)	0.050 (5)	0.304 (15)
H20A	0.5235	0.5275	0.2037	0.06*	0.304 (15)
H20B	0.5298	0.416	0.1226	0.06*	0.304 (15)
C21	1.1852 (3)	0.1752 (4)	0.7390 (3)	0.0278 (6)
C22	1.2089 (3)	0.1773 (4)	0.6054 (3)	0.0312 (6)
H22	1.1285	0.2002	0.5456	0.037*
C23	1.3508 (4)	0.1456 (4)	0.5606 (3)	0.0364 (7)
H23	1.3655	0.147	0.4713	0.044*
C24	1.4702 (4)	0.1119 (4)	0.6490 (4)	0.0414 (8)
H24	1.5659	0.0893	0.6197	0.05*
C25	1.4476 (4)	0.1118 (4)	0.7813 (3)	0.0380 (7)
H25	1.5278	0.0907	0.8401	0.046*
C26	1.3067 (3)	0.1429 (4)	0.8262 (3)	0.0325 (6)
H26	1.2926	0.1423	0.9153	0.039*
C31	0.9371 (3)	0.4102 (4)	0.8217 (3)	0.0282 (6)
C32	0.9929 (4)	0.5164 (4)	0.7448 (3)	0.0331 (7)
H32	1.063	0.4878	0.6839	0.04*
C33	0.9444 (4)	0.6660 (4)	0.7584 (3)	0.0379 (7)
H33	0.9824	0.7368	0.707	0.045*
C34	0.8397 (4)	0.7090 (4)	0.8483 (3)	0.0376 (7)
H34	0.8065	0.8091	0.857	0.045*
C35	0.7847 (4)	0.6031 (4)	0.9250 (4)	0.0404 (8)
H35	0.7141	0.6326	0.9852	0.048*
C36	0.8330 (3)	0.4529 (4)	0.9140 (3)	0.0349 (7)
H36	0.7965	0.3814	0.9674	0.042*
P1	1.00121 (8)	0.21439 (9)	0.80338 (7)	0.02397 (18)
Cl1	0.73685 (8)	0.14865 (9)	0.94644 (8)	0.03426 (19)
Pd	1	0	1	0.02362 (13)

	U11	U22	U33	U12	U13	U23
C11	0.0233 (14)	0.0424 (16)	0.0255 (14)	−0.0213 (13)	0.0092 (11)	−0.0135 (13)
C12	0.0306 (16)	0.0466 (18)	0.0424 (17)	−0.0231 (15)	0.0150 (13)	−0.0234 (15)
C13	0.0453 (19)	0.077 (3)	0.048 (2)	−0.046 (2)	0.0287 (16)	−0.044 (2)
C14	0.050 (2)	0.083 (3)	0.0261 (16)	−0.052 (2)	0.0107 (15)	−0.0155 (17)
C15	0.047 (2)	0.060 (2)	0.0327 (17)	−0.0375 (18)	−0.0034 (15)	−0.0030 (16)
C16	0.0333 (16)	0.0426 (17)	0.0327 (16)	−0.0243 (15)	0.0012 (13)	−0.0088 (14)
C17	0.029 (3)	0.041 (4)	0.033 (4)	−0.016 (3)	0.004 (3)	−0.013 (3)
C18	0.047 (3)	0.050 (4)	0.038 (3)	−0.020 (3)	−0.006 (2)	−0.015 (3)
C19	0.031 (8)	0.039 (8)	0.036 (8)	−0.016 (7)	0.006 (6)	−0.022 (6)
C20	0.052 (8)	0.064 (11)	0.030 (9)	−0.026 (7)	−0.002 (6)	−0.016 (8)
C21	0.0251 (14)	0.0305 (14)	0.0279 (14)	−0.0158 (12)	0.0084 (11)	−0.0094 (12)
C22	0.0293 (15)	0.0342 (15)	0.0303 (15)	−0.0178 (13)	0.0053 (12)	−0.0099 (12)
C23	0.0334 (17)	0.0416 (17)	0.0333 (16)	−0.0195 (14)	0.0155 (13)	−0.0139 (14)
C24	0.0271 (16)	0.0444 (18)	0.049 (2)	−0.0192 (15)	0.0156 (14)	−0.0136 (16)
C25	0.0285 (16)	0.0414 (17)	0.0406 (18)	−0.0198 (14)	0.0000 (13)	−0.0083 (14)
C26	0.0316 (16)	0.0376 (16)	0.0283 (15)	−0.0197 (13)	0.0054 (12)	−0.0095 (13)
C31	0.0245 (14)	0.0349 (15)	0.0241 (14)	−0.0131 (12)	0.0018 (11)	−0.0119 (12)
C32	0.0373 (16)	0.0405 (17)	0.0244 (14)	−0.0201 (14)	0.0083 (12)	−0.0144 (13)
C33	0.0447 (18)	0.0395 (17)	0.0318 (16)	−0.0231 (15)	0.0062 (14)	−0.0129 (14)
C34	0.0360 (17)	0.0398 (17)	0.0356 (17)	−0.0136 (14)	−0.0012 (13)	−0.0186 (14)
C35	0.0307 (16)	0.056 (2)	0.0425 (18)	−0.0186 (15)	0.0106 (14)	−0.0306 (16)
C36	0.0314 (16)	0.0473 (18)	0.0334 (16)	−0.0226 (14)	0.0095 (12)	−0.0194 (14)
P1	0.0213 (4)	0.0307 (4)	0.0205 (3)	−0.0149 (3)	0.0058 (3)	−0.0081 (3)
Cl1	0.0207 (3)	0.0380 (4)	0.0347 (4)	−0.0152 (3)	0.0042 (3)	−0.0039 (3)
Pd	0.01846 (18)	0.02981 (19)	0.02028 (18)	−0.01383 (14)	0.00523 (11)	−0.00526 (13)

C11—C16	1.373 (4)	C22—H22	0.93
C11—C12	1.391 (4)	C23—C24	1.380 (5)
C11—P1	1.820 (3)	C23—H23	0.93
C12—C13	1.397 (5)	C24—C25	1.385 (5)
C12—H12	0.93	C24—H24	0.93
C13—C14	1.387 (6)	C25—C26	1.378 (4)
C13—H13	0.93	C25—H25	0.93
C14—C15	1.371 (5)	C26—H26	0.93
C14—C19	1.498 (14)	C31—C32	1.385 (4)
C14—C17	1.511 (8)	C31—C36	1.398 (4)
C15—C16	1.392 (4)	C31—P1	1.827 (3)
C15—H15	0.93	C32—C33	1.395 (4)
C16—H16	0.93	C32—H32	0.93
C17—C18	1.298 (12)	C33—C34	1.382 (5)
C17—H17	0.93	C33—H33	0.93
C18—H18A	0.93	C34—C35	1.377 (5)
C18—H18B	0.93	C34—H34	0.93
C19—C20	1.29 (3)	C35—C36	1.388 (5)
C19—H19	0.93	C35—H35	0.93
C20—H20A	0.93	C36—H36	0.93
C20—H20B	0.93	P1—Pd	2.3366 (7)
C21—C22	1.393 (4)	Cl1—Pd	2.2966 (7)
C21—C26	1.395 (4)	Pd—Cl1i	2.2966 (7)
C21—P1	1.824 (3)	Pd—P1i	2.3366 (7)
C22—C23	1.386 (4)
C16—C11—C12	118.8 (3)	C22—C23—H23	120.1
C16—C11—P1	122.8 (2)	C23—C24—C25	120.1 (3)
C12—C11—P1	118.4 (2)	C23—C24—H24	120
C11—C12—C13	119.8 (3)	C25—C24—H24	120
C11—C12—H12	120.1	C26—C25—C24	120.3 (3)
C13—C12—H12	120.1	C26—C25—H25	119.9
C14—C13—C12	121.3 (3)	C24—C25—H25	119.9
C14—C13—H13	119.4	C25—C26—C21	120.5 (3)
C12—C13—H13	119.4	C25—C26—H26	119.8
C15—C14—C13	117.9 (3)	C21—C26—H26	119.8
C15—C14—C19	141.5 (8)	C32—C31—C36	119.7 (3)
C13—C14—C19	99.8 (8)	C32—C31—P1	120.0 (2)
C15—C14—C17	113.6 (5)	C36—C31—P1	120.3 (2)
C13—C14—C17	128.5 (4)	C31—C32—C33	120.2 (3)
C14—C15—C16	121.5 (3)	C31—C32—H32	119.9
C14—C15—H15	119.3	C33—C32—H32	119.9
C16—C15—H15	119.3	C34—C33—C32	120.0 (3)
C11—C16—C15	120.7 (3)	C34—C33—H33	120
C11—C16—H16	119.6	C32—C33—H33	120
C15—C16—H16	119.6	C35—C34—C33	119.8 (3)
C18—C17—C14	122.4 (7)	C35—C34—H34	120.1
C18—C17—H17	118.8	C33—C34—H34	120.1
C14—C17—H17	118.8	C34—C35—C36	121.1 (3)
C17—C18—H18A	120	C34—C35—H35	119.5
C17—C18—H18B	120	C36—C35—H35	119.5
H18A—C18—H18B	120	C35—C36—C31	119.3 (3)
C20—C19—C14	114.3 (15)	C35—C36—H36	120.4
C20—C19—H19	122.8	C31—C36—H36	120.4
C14—C19—H19	122.8	C11—P1—C21	103.88 (13)
C19—C20—H20A	120	C11—P1—C31	106.35 (13)
C19—C20—H20B	120	C21—P1—C31	102.82 (13)
H20A—C20—H20B	120	C11—P1—Pd	110.15 (9)
C22—C21—C26	118.6 (3)	C21—P1—Pd	116.81 (10)
C22—C21—P1	122.5 (2)	C31—P1—Pd	115.66 (9)
C26—C21—P1	118.9 (2)	Cl1—Pd—Cl1i	180
C23—C22—C21	120.8 (3)	Cl1—Pd—P1	85.83 (2)
C23—C22—H22	119.6	Cl1i—Pd—P1	94.17 (2)
C21—C22—H22	119.6	Cl1—Pd—P1i	94.17 (2)
C24—C23—C22	119.7 (3)	Cl1i—Pd—P1i	85.83 (2)
C24—C23—H23	120.1	P1—Pd—P1i	180
C16—C11—C12—C13	2.5 (4)	C32—C33—C34—C35	0.5 (5)
P1—C11—C12—C13	−176.1 (2)	C33—C34—C35—C36	0.2 (5)
C11—C12—C13—C14	−1.7 (4)	C34—C35—C36—C31	−1.1 (5)
C12—C13—C14—C15	−0.4 (5)	C32—C31—C36—C35	1.3 (4)
C12—C13—C14—C19	171.6 (5)	P1—C31—C36—C35	−179.3 (2)
C12—C13—C14—C17	−178.2 (4)	C16—C11—P1—C21	−101.2 (3)
C13—C14—C15—C16	1.6 (5)	C12—C11—P1—C21	77.3 (2)
C19—C14—C15—C16	−165.6 (9)	C16—C11—P1—C31	6.9 (3)
C17—C14—C15—C16	179.8 (4)	C12—C11—P1—C31	−174.6 (2)
C12—C11—C16—C15	−1.3 (4)	C16—C11—P1—Pd	132.9 (2)
P1—C11—C16—C15	177.2 (2)	C12—C11—P1—Pd	−48.6 (2)
C14—C15—C16—C11	−0.8 (5)	C22—C21—P1—C11	−2.7 (3)
C15—C14—C17—C18	167.1 (5)	C26—C21—P1—C11	176.8 (2)
C13—C14—C17—C18	−15.0 (7)	C22—C21—P1—C31	−113.5 (3)
C19—C14—C17—C18	5.3 (9)	C26—C21—P1—C31	66.1 (3)
C15—C14—C19—C20	−9.9 (16)	C22—C21—P1—Pd	118.8 (2)
C13—C14—C19—C20	−178.5 (10)	C26—C21—P1—Pd	−61.7 (3)
C17—C14—C19—C20	17.6 (9)	C32—C31—P1—C11	−85.8 (2)
C26—C21—C22—C23	0.9 (4)	C36—C31—P1—C11	94.9 (2)
P1—C21—C22—C23	−179.5 (2)	C32—C31—P1—C21	23.1 (3)
C21—C22—C23—C24	−0.2 (5)	C36—C31—P1—C21	−156.3 (2)
C22—C23—C24—C25	−0.8 (5)	C32—C31—P1—Pd	151.6 (2)
C23—C24—C25—C26	0.9 (5)	C36—C31—P1—Pd	−27.8 (3)
C24—C25—C26—C21	−0.2 (5)	C11—P1—Pd—Cl1	−48.46 (10)
C22—C21—C26—C25	−0.7 (4)	C21—P1—Pd—Cl1	−166.62 (11)
P1—C21—C26—C25	179.7 (2)	C31—P1—Pd—Cl1	72.14 (10)
C36—C31—C32—C33	−0.6 (4)	C11—P1—Pd—Cl1i	131.54 (10)
P1—C31—C32—C33	180.0 (2)	C21—P1—Pd—Cl1i	13.38 (11)
C31—C32—C33—C34	−0.3 (5)	C31—P1—Pd—Cl1i	−107.86 (10)