Acta Cryst. (2009). E65, m1536 [ doi:10.1107/S1600536809046261 ]
The structure of the title compound, [PdCl2(C21H21O3P)2]·C6H6, shows a square-planar geometry for the PdII atom within a Cl2[P(PhOMe)3]2 ligand set. The crystal structure contains benzene as solvent. The PdII atom sits on a centre of inversion and therefore the asymmetric unit contains the PdII atom, one Cl atom, one tris(4-methoxyphenyl)phosphine ligand and one half of the benzene solvent molecule.
Tris-(4-methoxyphenyl)phosphine (704 mg, 0.2 mmol) was added to a solution of lithium chloride (85 mg, 0.2 mmol) and palladium(II) chloride (177 mg, 0.1 mmol) in 15 ml me thanol. The mixture was heated under reflux in an atmosphere of nitrogen for 1 h resulting in the formation of the product as a yellow precipitate. The solution was allowed to cool to room temperature and the product (710 mg) was collected by filtration, washed with fresh methanol and dried under vacuum. The product was recrystallized from 1:1 ethyl acetate:benzene to furnish yellow plates (m. p. > 250°C, decomp.) A suitable single-crystal was selected for the single-crystal X-ray diffraction analysis.
H atoms were geometrically positioned and refined in the riding-model approximation, with C—H = 0.97 Å, N—H = 0.89 Å, and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(N). For (I), the highest peak in the final difference map is 0.98Å from C15 and the deepest hole is 0.01Å from Pd1.
Data collection: SMART-NT (Bruker, 1999); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2009).
![[Figure 1]](./ez2192fig1thm.gif)
| Fig. 1. : Molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. Atoms labelled with (i) are at symmetry position (– x, – y, – z) and atoms labelled with (ii) are at symmetry position (– x + 1, – y + 1, – z + 1) |
| [PdCl2(C21H21O3P)2]·C6H6 | Z = 1 |
| Mr = 960.10 | F(000) = 494 |
| Triclinic, P1 | Dx = 1.382 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.9338 (2) Å | Cell parameters from 9954 reflections |
| b = 12.1886 (3) Å | θ = 1.7–28.3° |
| c = 12.5268 (3) Å | µ = 0.63 mm−1 |
| α = 85.981 (3)° | T = 295 K |
| β = 78.840 (2)° | Flat, yellow |
| γ = 76.155 (2)° | 0.34 × 0.24 × 0.10 mm |
| V = 1153.57 (5) Å3 |
| Bruker SMART CCD diffractometer | 5781 independent reflections |
| Radiation source: fine-focus sealed tube | 4546 reflections with I > 2σ(I) |
| graphite | Rint = 0.046 |
| φ and ω scans | θmax = 28.4°, θmin = 1.7° |
| Absorption correction: multi-scan (APEX2 Ax-Scale; Bruker, 2008) | h = −10→10 |
| Tmin = 0.813, Tmax = 0.939 | k = −16→16 |
| 31847 measured reflections | l = −16→16 |
| 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.097 | H-atom parameters constrained |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.8985P] where P = (Fo2 + 2Fc2)/3 |
| 5781 reflections | (Δ/σ)max < 0.001 |
| 271 parameters | Δρmax = 1.26 e Å−3 |
| 0 restraints | Δρmin = −0.53 e Å−3 |
| [PdCl2(C21H21O3P)2]·C6H6 | γ = 76.155 (2)° |
| Mr = 960.10 | V = 1153.57 (5) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 7.9338 (2) Å | Mo Kα radiation |
| b = 12.1886 (3) Å | µ = 0.63 mm−1 |
| c = 12.5268 (3) Å | T = 295 K |
| α = 85.981 (3)° | 0.34 × 0.24 × 0.10 mm |
| β = 78.840 (2)° |
| Bruker SMART CCD diffractometer | 5781 independent reflections |
| Absorption correction: multi-scan (APEX2 Ax-Scale; Bruker, 2008) | 4546 reflections with I > 2σ(I) |
| Tmin = 0.813, Tmax = 0.939 | Rint = 0.046 |
| 31847 measured reflections | θmax = 28.4° |
| R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
| wR(F2) = 0.097 | Δρmax = 1.26 e Å−3 |
| S = 1.08 | Δρmin = −0.53 e Å−3 |
| 5781 reflections | Absolute structure: ? |
| 271 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| C1 | 0.4425 (16) | 0.4281 (7) | 0.5761 (6) | 0.155 (3) | |
| H1 | 0.4046 | 0.3780 | 0.6295 | 0.186* | |
| C2 | 0.5827 (15) | 0.4708 (8) | 0.5889 (6) | 0.157 (3) | |
| H2 | 0.6361 | 0.4503 | 0.6495 | 0.188* | |
| C3 | 0.3558 (14) | 0.4537 (7) | 0.4915 (8) | 0.164 (3) | |
| H3 | 0.2608 | 0.4232 | 0.4866 | 0.197* | |
| C11 | 0.0548 (3) | 0.1003 (2) | −0.2660 (2) | 0.0322 (5) | |
| C12 | −0.0842 (4) | 0.0505 (3) | −0.2715 (2) | 0.0394 (6) | |
| H12 | −0.1180 | 0.0008 | −0.2162 | 0.047* | |
| C13 | −0.1725 (4) | 0.0744 (3) | −0.3587 (2) | 0.0457 (7) | |
| H13 | −0.2650 | 0.0406 | −0.3614 | 0.055* | |
| C14 | −0.1248 (4) | 0.1475 (3) | −0.4413 (2) | 0.0415 (6) | |
| C15 | 0.0146 (4) | 0.1971 (3) | −0.4377 (2) | 0.0491 (8) | |
| H15 | 0.0490 | 0.2459 | −0.4937 | 0.059* | |
| C16 | 0.1017 (4) | 0.1736 (3) | −0.3504 (2) | 0.0451 (7) | |
| H16 | 0.1941 | 0.2076 | −0.3481 | 0.054* | |
| C17 | −0.1700 (5) | 0.2373 (4) | −0.6136 (3) | 0.0663 (10) | |
| H17A | −0.1778 | 0.3112 | −0.5882 | 0.099* | |
| H17B | −0.2476 | 0.2429 | −0.6647 | 0.099* | |
| H17C | −0.0508 | 0.2058 | −0.6484 | 0.099* | |
| C21 | 0.2612 (3) | 0.1876 (2) | −0.1422 (2) | 0.0319 (5) | |
| C22 | 0.4426 (4) | 0.1803 (2) | −0.1504 (2) | 0.0379 (6) | |
| H22 | 0.5220 | 0.1107 | −0.1627 | 0.046* | |
| C23 | 0.5046 (4) | 0.2750 (3) | −0.1406 (3) | 0.0462 (7) | |
| H23 | 0.6252 | 0.2685 | −0.1460 | 0.055* | |
| C24 | 0.3887 (4) | 0.3800 (2) | −0.1227 (2) | 0.0419 (7) | |
| C25 | 0.2087 (4) | 0.3885 (2) | −0.1136 (2) | 0.0417 (7) | |
| H25 | 0.1297 | 0.4582 | −0.1011 | 0.050* | |
| C26 | 0.1472 (4) | 0.2935 (2) | −0.1233 (2) | 0.0383 (6) | |
| H26 | 0.0264 | 0.3004 | −0.1169 | 0.046* | |
| C27 | 0.3489 (6) | 0.5791 (3) | −0.1038 (4) | 0.0781 (13) | |
| H27A | 0.2900 | 0.5975 | −0.1650 | 0.117* | |
| H27B | 0.4168 | 0.6336 | −0.0997 | 0.117* | |
| H27C | 0.2628 | 0.5801 | −0.0382 | 0.117* | |
| C31 | 0.3704 (3) | −0.0450 (2) | −0.2019 (2) | 0.0305 (5) | |
| C32 | 0.4241 (4) | −0.0750 (2) | −0.3103 (2) | 0.0381 (6) | |
| H32 | 0.3637 | −0.0348 | −0.3627 | 0.046* | |
| C33 | 0.5670 (4) | −0.1644 (3) | −0.3409 (2) | 0.0465 (7) | |
| H33 | 0.6017 | −0.1840 | −0.4136 | 0.056* | |
| C34 | 0.6591 (4) | −0.2253 (2) | −0.2634 (3) | 0.0408 (6) | |
| C35 | 0.6116 (4) | −0.1934 (3) | −0.1561 (3) | 0.0438 (7) | |
| H35 | 0.6766 | −0.2308 | −0.1046 | 0.053* | |
| C36 | 0.4660 (4) | −0.1053 (2) | −0.1256 (2) | 0.0406 (6) | |
| H36 | 0.4315 | −0.0861 | −0.0528 | 0.049* | |
| C37 | 0.8756 (5) | −0.3895 (3) | −0.2234 (4) | 0.0722 (11) | |
| H37A | 0.9291 | −0.3483 | −0.1822 | 0.108* | |
| H37B | 0.9644 | −0.4495 | −0.2604 | 0.108* | |
| H37C | 0.7882 | −0.4206 | −0.1751 | 0.108* | |
| O1 | −0.2204 (3) | 0.1654 (2) | −0.52266 (18) | 0.0592 (6) | |
| O2 | 0.4641 (3) | 0.46844 (19) | −0.1165 (2) | 0.0626 (7) | |
| O3 | 0.7933 (3) | −0.31468 (19) | −0.3017 (2) | 0.0576 (6) | |
| P1 | 0.17506 (8) | 0.06402 (5) | −0.15376 (5) | 0.02933 (15) | |
| Cl1 | −0.05138 (11) | 0.16975 (6) | 0.08394 (6) | 0.04878 (19) | |
| Pd1 | 0.0000 | 0.0000 | 0.0000 | 0.02850 (9) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.264 (12) | 0.110 (5) | 0.087 (5) | −0.034 (6) | −0.030 (6) | −0.009 (4) |
| C2 | 0.244 (11) | 0.137 (7) | 0.080 (5) | −0.018 (7) | −0.037 (6) | −0.015 (5) |
| C3 | 0.256 (11) | 0.129 (6) | 0.109 (6) | −0.046 (7) | −0.024 (7) | −0.038 (5) |
| C11 | 0.0305 (13) | 0.0349 (14) | 0.0304 (13) | −0.0055 (11) | −0.0069 (10) | 0.0006 (10) |
| C12 | 0.0387 (15) | 0.0453 (16) | 0.0373 (14) | −0.0170 (13) | −0.0083 (12) | 0.0075 (12) |
| C13 | 0.0408 (16) | 0.0573 (19) | 0.0461 (16) | −0.0236 (14) | −0.0117 (13) | 0.0031 (14) |
| C14 | 0.0414 (15) | 0.0484 (17) | 0.0375 (15) | −0.0109 (13) | −0.0138 (12) | 0.0001 (13) |
| C15 | 0.0554 (19) | 0.066 (2) | 0.0372 (15) | −0.0340 (16) | −0.0158 (14) | 0.0154 (14) |
| C16 | 0.0459 (16) | 0.0534 (18) | 0.0454 (16) | −0.0264 (14) | −0.0173 (13) | 0.0123 (14) |
| C17 | 0.078 (3) | 0.084 (3) | 0.051 (2) | −0.036 (2) | −0.0331 (19) | 0.0202 (19) |
| C21 | 0.0367 (14) | 0.0303 (13) | 0.0295 (12) | −0.0101 (11) | −0.0070 (10) | 0.0036 (10) |
| C22 | 0.0368 (14) | 0.0323 (14) | 0.0446 (15) | −0.0063 (11) | −0.0088 (12) | −0.0016 (12) |
| C23 | 0.0355 (15) | 0.0440 (17) | 0.063 (2) | −0.0147 (13) | −0.0126 (14) | 0.0005 (14) |
| C24 | 0.0517 (17) | 0.0324 (15) | 0.0478 (16) | −0.0156 (13) | −0.0181 (14) | 0.0039 (12) |
| C25 | 0.0450 (16) | 0.0287 (14) | 0.0496 (16) | −0.0043 (12) | −0.0109 (13) | 0.0018 (12) |
| C26 | 0.0340 (14) | 0.0343 (14) | 0.0464 (16) | −0.0079 (11) | −0.0089 (12) | 0.0042 (12) |
| C27 | 0.079 (3) | 0.0346 (18) | 0.129 (4) | −0.0176 (18) | −0.033 (3) | 0.000 (2) |
| C31 | 0.0321 (13) | 0.0273 (13) | 0.0333 (13) | −0.0080 (10) | −0.0079 (10) | 0.0000 (10) |
| C32 | 0.0359 (14) | 0.0416 (16) | 0.0358 (14) | −0.0051 (12) | −0.0091 (11) | −0.0008 (12) |
| C33 | 0.0428 (16) | 0.0565 (19) | 0.0360 (15) | −0.0031 (14) | −0.0041 (12) | −0.0101 (13) |
| C34 | 0.0316 (14) | 0.0369 (15) | 0.0525 (17) | −0.0071 (12) | −0.0040 (12) | −0.0053 (13) |
| C35 | 0.0431 (16) | 0.0401 (16) | 0.0491 (17) | −0.0053 (13) | −0.0182 (13) | 0.0048 (13) |
| C36 | 0.0462 (16) | 0.0403 (16) | 0.0345 (14) | −0.0048 (13) | −0.0124 (12) | −0.0008 (12) |
| C37 | 0.061 (2) | 0.054 (2) | 0.090 (3) | 0.0119 (18) | −0.018 (2) | −0.001 (2) |
| O1 | 0.0633 (15) | 0.0806 (17) | 0.0476 (13) | −0.0328 (13) | −0.0299 (11) | 0.0164 (12) |
| O2 | 0.0640 (15) | 0.0374 (12) | 0.0955 (19) | −0.0198 (11) | −0.0262 (14) | −0.0028 (12) |
| O3 | 0.0453 (12) | 0.0516 (13) | 0.0654 (15) | 0.0089 (10) | −0.0076 (11) | −0.0073 (11) |
| P1 | 0.0311 (3) | 0.0287 (3) | 0.0285 (3) | −0.0080 (3) | −0.0054 (3) | 0.0009 (3) |
| Cl1 | 0.0675 (5) | 0.0326 (4) | 0.0444 (4) | −0.0180 (3) | 0.0051 (3) | −0.0086 (3) |
| Pd1 | 0.03329 (16) | 0.02494 (15) | 0.02737 (15) | −0.00770 (11) | −0.00467 (11) | −0.00023 (10) |
| C1—C3 | 1.351 (11) | C24—O2 | 1.366 (4) |
| C1—C2 | 1.375 (12) | C24—C25 | 1.390 (4) |
| C1—H1 | 0.9300 | C25—C26 | 1.380 (4) |
| C2—C3i | 1.413 (11) | C25—H25 | 0.9300 |
| C2—H2 | 0.9300 | C26—H26 | 0.9300 |
| C3—C2i | 1.413 (11) | C27—O2 | 1.436 (4) |
| C3—H3 | 0.9300 | C27—H27A | 0.9600 |
| C11—C16 | 1.388 (4) | C27—H27B | 0.9600 |
| C11—C12 | 1.395 (4) | C27—H27C | 0.9600 |
| C11—P1 | 1.820 (3) | C31—C32 | 1.389 (4) |
| C12—C13 | 1.387 (4) | C31—C36 | 1.394 (4) |
| C12—H12 | 0.9300 | C31—P1 | 1.815 (3) |
| C13—C14 | 1.374 (4) | C32—C33 | 1.386 (4) |
| C13—H13 | 0.9300 | C32—H32 | 0.9300 |
| C14—O1 | 1.360 (3) | C33—C34 | 1.393 (4) |
| C14—C15 | 1.392 (4) | C33—H33 | 0.9300 |
| C15—C16 | 1.382 (4) | C34—O3 | 1.368 (3) |
| C15—H15 | 0.9300 | C34—C35 | 1.381 (4) |
| C16—H16 | 0.9300 | C35—C36 | 1.388 (4) |
| C17—O1 | 1.441 (4) | C35—H35 | 0.9300 |
| C17—H17A | 0.9600 | C36—H36 | 0.9300 |
| C17—H17B | 0.9600 | C37—O3 | 1.434 (4) |
| C17—H17C | 0.9600 | C37—H37A | 0.9600 |
| C21—C26 | 1.394 (4) | C37—H37B | 0.9600 |
| C21—C22 | 1.404 (4) | C37—H37C | 0.9600 |
| C21—P1 | 1.821 (3) | P1—Pd1 | 2.3496 (6) |
| C22—C23 | 1.380 (4) | Cl1—Pd1 | 2.2995 (7) |
| C22—H22 | 0.9300 | Pd1—Cl1ii | 2.2995 (7) |
| C23—C24 | 1.389 (4) | Pd1—P1ii | 2.3496 (6) |
| C23—H23 | 0.9300 | ||
| C3—C1—C2 | 124.8 (9) | C25—C26—C21 | 121.8 (3) |
| C3—C1—H1 | 117.6 | C25—C26—H26 | 119.1 |
| C2—C1—H1 | 117.6 | C21—C26—H26 | 119.1 |
| C1—C2—C3i | 118.8 (8) | O2—C27—H27A | 109.5 |
| C1—C2—H2 | 120.6 | O2—C27—H27B | 109.5 |
| C3i—C2—H2 | 120.6 | H27A—C27—H27B | 109.5 |
| C1—C3—C2i | 116.3 (9) | O2—C27—H27C | 109.5 |
| C1—C3—H3 | 121.8 | H27A—C27—H27C | 109.5 |
| C2i—C3—H3 | 121.8 | H27B—C27—H27C | 109.5 |
| C16—C11—C12 | 118.0 (2) | C32—C31—C36 | 118.4 (2) |
| C16—C11—P1 | 121.9 (2) | C32—C31—P1 | 123.13 (19) |
| C12—C11—P1 | 120.1 (2) | C36—C31—P1 | 118.4 (2) |
| C13—C12—C11 | 120.5 (3) | C33—C32—C31 | 120.5 (3) |
| C13—C12—H12 | 119.7 | C33—C32—H32 | 119.8 |
| C11—C12—H12 | 119.7 | C31—C32—H32 | 119.8 |
| C14—C13—C12 | 120.7 (3) | C32—C33—C34 | 120.4 (3) |
| C14—C13—H13 | 119.6 | C32—C33—H33 | 119.8 |
| C12—C13—H13 | 119.6 | C34—C33—H33 | 119.8 |
| O1—C14—C13 | 116.0 (3) | O3—C34—C35 | 124.8 (3) |
| O1—C14—C15 | 124.5 (3) | O3—C34—C33 | 115.6 (3) |
| C13—C14—C15 | 119.5 (3) | C35—C34—C33 | 119.7 (3) |
| C16—C15—C14 | 119.6 (3) | C34—C35—C36 | 119.5 (3) |
| C16—C15—H15 | 120.2 | C34—C35—H35 | 120.2 |
| C14—C15—H15 | 120.2 | C36—C35—H35 | 120.2 |
| C15—C16—C11 | 121.6 (3) | C35—C36—C31 | 121.4 (3) |
| C15—C16—H16 | 119.2 | C35—C36—H36 | 119.3 |
| C11—C16—H16 | 119.2 | C31—C36—H36 | 119.3 |
| O1—C17—H17A | 109.5 | O3—C37—H37A | 109.5 |
| O1—C17—H17B | 109.5 | O3—C37—H37B | 109.5 |
| H17A—C17—H17B | 109.5 | H37A—C37—H37B | 109.5 |
| O1—C17—H17C | 109.5 | O3—C37—H37C | 109.5 |
| H17A—C17—H17C | 109.5 | H37A—C37—H37C | 109.5 |
| H17B—C17—H17C | 109.5 | H37B—C37—H37C | 109.5 |
| C26—C21—C22 | 117.5 (2) | C14—O1—C17 | 118.0 (2) |
| C26—C21—P1 | 120.6 (2) | C24—O2—C27 | 117.4 (3) |
| C22—C21—P1 | 122.0 (2) | C34—O3—C37 | 117.7 (3) |
| C23—C22—C21 | 120.9 (3) | C31—P1—C11 | 106.73 (12) |
| C23—C22—H22 | 119.5 | C31—P1—C21 | 104.02 (12) |
| C21—C22—H22 | 119.5 | C11—P1—C21 | 104.27 (12) |
| C22—C23—C24 | 120.6 (3) | C31—P1—Pd1 | 111.03 (8) |
| C22—C23—H23 | 119.7 | C11—P1—Pd1 | 111.08 (9) |
| C24—C23—H23 | 119.7 | C21—P1—Pd1 | 118.81 (9) |
| O2—C24—C23 | 115.9 (3) | Cl1ii—Pd1—Cl1 | 180.00 (4) |
| O2—C24—C25 | 124.9 (3) | Cl1ii—Pd1—P1 | 88.38 (2) |
| C23—C24—C25 | 119.2 (3) | Cl1—Pd1—P1 | 91.62 (2) |
| C26—C25—C24 | 120.0 (3) | Cl1ii—Pd1—P1ii | 91.62 (2) |
| C26—C25—H25 | 120.0 | Cl1—Pd1—P1ii | 88.38 (2) |
| C24—C25—H25 | 120.0 | P1—Pd1—P1ii | 180.00 (3) |
| C3—C1—C2—C3i | −0.6 (15) | P1—C31—C36—C35 | 176.8 (2) |
| C2—C1—C3—C2i | 0.5 (15) | C13—C14—O1—C17 | −177.2 (3) |
| C16—C11—C12—C13 | −0.3 (4) | C15—C14—O1—C17 | 2.6 (5) |
| P1—C11—C12—C13 | −177.6 (2) | C23—C24—O2—C27 | 176.8 (3) |
| C11—C12—C13—C14 | 0.0 (5) | C25—C24—O2—C27 | −2.5 (5) |
| C12—C13—C14—O1 | −179.7 (3) | C35—C34—O3—C37 | 8.5 (5) |
| C12—C13—C14—C15 | 0.6 (5) | C33—C34—O3—C37 | −171.3 (3) |
| O1—C14—C15—C16 | 179.4 (3) | C32—C31—P1—C11 | 10.3 (3) |
| C13—C14—C15—C16 | −0.9 (5) | C36—C31—P1—C11 | −166.3 (2) |
| C14—C15—C16—C11 | 0.6 (5) | C32—C31—P1—C21 | −99.6 (2) |
| C12—C11—C16—C15 | 0.0 (5) | C36—C31—P1—C21 | 83.8 (2) |
| P1—C11—C16—C15 | 177.2 (3) | C32—C31—P1—Pd1 | 131.5 (2) |
| C26—C21—C22—C23 | −0.3 (4) | C36—C31—P1—Pd1 | −45.2 (2) |
| P1—C21—C22—C23 | −179.5 (2) | C16—C11—P1—C31 | −80.9 (3) |
| C21—C22—C23—C24 | −0.2 (5) | C12—C11—P1—C31 | 96.3 (2) |
| C22—C23—C24—O2 | −178.6 (3) | C16—C11—P1—C21 | 28.8 (3) |
| C22—C23—C24—C25 | 0.6 (5) | C12—C11—P1—C21 | −154.0 (2) |
| O2—C24—C25—C26 | 178.8 (3) | C16—C11—P1—Pd1 | 157.9 (2) |
| C23—C24—C25—C26 | −0.4 (4) | C12—C11—P1—Pd1 | −24.9 (2) |
| C24—C25—C26—C21 | −0.1 (4) | C26—C21—P1—C31 | 170.1 (2) |
| C22—C21—C26—C25 | 0.5 (4) | C22—C21—P1—C31 | −10.8 (2) |
| P1—C21—C26—C25 | 179.7 (2) | C26—C21—P1—C11 | 58.4 (2) |
| C36—C31—C32—C33 | 1.4 (4) | C22—C21—P1—C11 | −122.5 (2) |
| P1—C31—C32—C33 | −175.3 (2) | C26—C21—P1—Pd1 | −65.9 (2) |
| C31—C32—C33—C34 | −0.2 (5) | C22—C21—P1—Pd1 | 113.2 (2) |
| C32—C33—C34—O3 | 177.4 (3) | C31—P1—Pd1—Cl1ii | −41.94 (9) |
| C32—C33—C34—C35 | −2.4 (5) | C11—P1—Pd1—Cl1ii | 76.66 (10) |
| O3—C34—C35—C36 | −176.1 (3) | C21—P1—Pd1—Cl1ii | −162.45 (10) |
| C33—C34—C35—C36 | 3.7 (5) | C31—P1—Pd1—Cl1 | 138.06 (9) |
| C34—C35—C36—C31 | −2.6 (5) | C11—P1—Pd1—Cl1 | −103.34 (10) |
| C32—C31—C36—C35 | 0.0 (4) | C21—P1—Pd1—Cl1 | 17.55 (10) |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z. |
The authors acknowledge the University of the Witwatersrand for their facilities and the use of the diffractometer in the Jan Boeyens Structural Chemistry Laboratory.
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The palladium-catalysed methoxycarbonylation (Robertson & Cole-Hamilton, 2002) of 1-alkenes is an active area of research. The palladium complexes (Ar3P)2PdX2 (X = Cl, DMS, OTf etc.) are the preferred catalysts but most quantitative studies have been carried out with complexes where the phosphine ligand is limited to triphenylphosphine. The X-ray structures (Van Leeuwen et al., 2003 and Williams et al., 2008) of several of this class of palladium(II) complexes have been determined. Our studies (Williams et al., 2008) on the effect of substituents on the triarylphosphine ligands on regioselectivity and reaction rate showed trans-dichloro-bis[tris-(4-methoxy)phosphine] palladium(II) to be an exceptionally efficient catalyst for the production of linear esters from 1-alkenes at high rates.
The structure of the title compound (I), [PdCl2(C42H42P2O6).C6H6] shows a square planar geometry for the PdII atom within the Cl2(P(PhOMe)3) ligand set. The crystal structure contains benzene as a solvate. The solvent molecule exhibits noticeable disorder but this disorder was not modelled. The palladium atom sits on a centre of inversion and therefore the asymmetric unit contains the palladium atom, one chlorine atom, one tris-(4-methoxyphenyl)phenylphosphine ligand and one half of the benzene solvent molecule.