Literature DB >> 21578097

trans-Bis[bis-(2-methoxy-phen-yl)phenyl-phosphine-κP]dichloridopalladium(II).

Charmaine van Blerk1, Cedric W Holzapfel.   

Abstract

The structure of the title compound, [PdCl(2)(C(20)H(19)O(2)P)(2)], shows a square-planar geometry for the Pd(II) ion within a Cl(2)Pd[PPh(PhOMe)(2)](2) ligand set. The Pd(II) atom sits on an inversion centre and therefore the asymmetric unit contains the Pd(II) atom, one Cl atom and one bis-(2-methoxy-phen-yl)phenyl-phosphine ligand. The trans arrangement of ligands is also imposed by symmetry.

Entities:  

Year:  2009        PMID： 21578097      PMCID： PMC2971441          DOI： 10.1107/S1600536809040744

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures of similar palladium complexes and their use in methoxy­carbonyl­ation reactions, see: Robertson & Cole-Hamilton (2002 ▶); Van Leeuwen et al. (2003 ▶); Williams et al. (2008 ▶).

Experimental

Crystal data

[PdCl2(C20H19O2P)2] M = 821.94 Monoclinic, a = 9.1617 (2) Å b = 12.7203 (3) Å c = 16.4939 (4) Å β = 94.114 (1)° V = 1917.24 (8) Å3 Z = 2 Mo Kα radiation μ = 0.75 mm−1 T = 296 K 0.22 × 0.18 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (; Bruker, 2008 ▶) T min = 0.853, T max = 0.916 23435 measured reflections 4750 independent reflections 3339 reflections with I > 2σ(I) R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.089 S = 1.02 4750 reflections 225 parameters H-atom parameters constrained Δρmax = 0.63 e Å−3 Δρmin = −0.38 e Å−3 Data collection: SMART-NT (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040744/bh2252sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040744/bh2252Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[PdCl2(C20H19O2P)2]F(000) = 840
Mr = 821.94Dx = 1.424 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5078 reflections
a = 9.1617 (2) Åθ = 2.5–24.7°
b = 12.7203 (3) ŵ = 0.75 mm−1
c = 16.4939 (4) ÅT = 296 K
β = 94.114 (1)°Block, yellow
V = 1917.24 (8) Å30.22 × 0.18 × 0.12 mm
Z = 2
Bruker SMART CCD diffractometer4750 independent reflections
Radiation source: fine-focus sealed tube3339 reflections with I > 2σ(I)
graphiteRint = 0.064
φ and ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (APEX AXScale; Bruker, 2008)h = −12→12
Tmin = 0.853, Tmax = 0.916k = −16→16
23435 measured reflectionsl = −21→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0441P)2] where P = (Fo2 + 2Fc2)/3
4750 reflections(Δ/σ)max = 0.001
225 parametersΔρmax = 0.63 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
0 constraints
xyzUiso*/Ueq
C110.0228 (3)0.1927 (2)−0.15944 (16)0.0323 (6)
C120.0094 (3)0.1268 (2)−0.22659 (16)0.0401 (7)
H12−0.04320.0646−0.22400.048*
C130.0734 (3)0.1526 (3)−0.29741 (18)0.0505 (8)
H130.06470.1072−0.34170.061*
C140.1500 (3)0.2454 (3)−0.3024 (2)0.0528 (8)
H140.19270.2628−0.35010.063*
C150.1626 (3)0.3112 (3)−0.2373 (2)0.0505 (8)
H150.21280.3744−0.24090.061*
C160.1016 (3)0.2850 (2)−0.16577 (18)0.0426 (7)
H160.11360.3299−0.12130.051*
C21−0.2607 (3)0.1459 (2)−0.10562 (17)0.0363 (6)
C22−0.3400 (3)0.0578 (2)−0.08536 (18)0.0434 (7)
H22−0.29540.0076−0.05080.052*
C23−0.4839 (3)0.0426 (3)−0.1152 (2)0.0569 (9)
H23−0.5358−0.0163−0.10020.068*
C24−0.5481 (4)0.1156 (3)−0.1671 (2)0.0670 (10)
H24−0.64440.1055−0.18760.080*
C25−0.4735 (4)0.2040 (3)−0.1898 (2)0.0631 (10)
H25−0.51910.2525−0.22540.076*
C26−0.3300 (3)0.2201 (3)−0.15904 (19)0.0472 (8)
C27−0.3017 (6)0.3742 (4)−0.2385 (3)0.1117 (19)
H27A−0.31800.3354−0.28820.167*
H27B−0.23110.4286−0.24540.167*
H27C−0.39210.4052−0.22450.167*
C31−0.0464 (3)0.2692 (2)−0.00191 (17)0.0403 (7)
C32−0.1582 (4)0.3370 (2)0.0142 (2)0.0518 (8)
H32−0.25100.3276−0.01140.062*
C33−0.1318 (5)0.4201 (3)0.0691 (2)0.0707 (11)
H33−0.20660.46640.07960.085*
C340.0048 (6)0.4326 (3)0.1071 (2)0.0805 (13)
H340.02120.48690.14440.097*
C350.1175 (5)0.3675 (3)0.0916 (2)0.0737 (12)
H350.20990.37790.11750.088*
C360.0933 (4)0.2854 (2)0.03693 (19)0.0505 (8)
C370.3458 (4)0.2356 (4)0.0401 (3)0.1033 (17)
H37A0.37050.30480.02240.155*
H37B0.40600.18470.01540.155*
H37C0.36180.23120.09810.155*
O1−0.2494 (2)0.30626 (18)−0.17624 (15)0.0639 (7)
O20.1969 (2)0.21487 (18)0.01702 (15)0.0628 (7)
P1−0.06893 (7)0.15556 (5)−0.06890 (4)0.03007 (16)
Cl10.12498 (8)−0.06305 (6)−0.10623 (4)0.04534 (19)
Pd10.00000.00000.00000.02642 (9)
U11U22U33U12U13U23
C110.0277 (13)0.0311 (14)0.0378 (14)0.0047 (11)0.0009 (11)0.0057 (11)
C120.0412 (16)0.0401 (16)0.0384 (16)−0.0050 (13)−0.0002 (13)0.0031 (13)
C130.056 (2)0.059 (2)0.0359 (16)0.0035 (16)0.0020 (15)0.0028 (15)
C140.0448 (19)0.069 (2)0.0461 (18)0.0056 (17)0.0128 (15)0.0177 (17)
C150.0432 (18)0.0463 (19)0.063 (2)−0.0063 (15)0.0130 (16)0.0168 (16)
C160.0434 (17)0.0356 (16)0.0492 (17)−0.0033 (13)0.0056 (14)0.0043 (13)
C210.0268 (14)0.0406 (16)0.0415 (15)0.0064 (12)0.0030 (12)0.0073 (12)
C220.0336 (16)0.0468 (18)0.0492 (17)0.0012 (13)0.0001 (13)0.0083 (14)
C230.0321 (17)0.062 (2)0.076 (2)−0.0062 (15)−0.0007 (16)0.0080 (19)
C240.0341 (18)0.091 (3)0.074 (2)0.0017 (19)−0.0093 (17)0.004 (2)
C250.0407 (19)0.080 (3)0.067 (2)0.0151 (18)−0.0095 (17)0.022 (2)
C260.0381 (17)0.0505 (19)0.0529 (18)0.0081 (14)0.0027 (14)0.0131 (15)
C270.128 (4)0.086 (3)0.114 (4)−0.004 (3)−0.035 (3)0.063 (3)
C310.0531 (18)0.0263 (14)0.0425 (16)0.0021 (12)0.0100 (15)0.0037 (12)
C320.062 (2)0.0367 (17)0.060 (2)0.0031 (15)0.0236 (17)0.0025 (15)
C330.099 (3)0.039 (2)0.079 (3)0.009 (2)0.046 (2)−0.0043 (19)
C340.124 (4)0.054 (3)0.064 (3)−0.007 (3)0.016 (3)−0.018 (2)
C350.102 (3)0.049 (2)0.068 (2)−0.010 (2)−0.014 (2)−0.0157 (19)
C360.067 (2)0.0352 (16)0.0484 (18)−0.0089 (15)−0.0040 (16)−0.0039 (14)
C370.059 (3)0.094 (3)0.151 (4)−0.009 (2)−0.033 (3)−0.026 (3)
O10.0490 (13)0.0574 (14)0.0837 (17)0.0081 (11)−0.0064 (12)0.0361 (13)
O20.0521 (14)0.0522 (14)0.0802 (16)0.0009 (11)−0.0218 (12)−0.0140 (12)
P10.0294 (3)0.0265 (3)0.0342 (4)0.0024 (3)0.0015 (3)0.0036 (3)
Cl10.0549 (5)0.0435 (4)0.0395 (4)0.0124 (3)0.0169 (3)0.0021 (3)
Pd10.02524 (14)0.02514 (14)0.02887 (14)0.00229 (12)0.00193 (10)0.00150 (12)
C11—C161.386 (4)C27—O11.400 (4)
C11—C121.387 (4)C27—H27A0.9600
C11—P11.827 (3)C27—H27B0.9600
C12—C131.383 (4)C27—H27C0.9600
C12—H120.9300C31—C321.379 (4)
C13—C141.379 (4)C31—C361.405 (4)
C13—H130.9300C31—P11.822 (3)
C14—C151.361 (5)C32—C331.402 (5)
C14—H140.9300C32—H320.9300
C15—C161.382 (4)C33—C341.368 (6)
C15—H150.9300C33—H330.9300
C16—H160.9300C34—C351.362 (6)
C21—C221.390 (4)C34—H340.9300
C21—C261.410 (4)C35—C361.388 (4)
C21—P11.821 (3)C35—H350.9300
C22—C231.387 (4)C36—O21.363 (4)
C22—H220.9300C37—O21.414 (4)
C23—C241.367 (5)C37—H37A0.9600
C23—H230.9300C37—H37B0.9600
C24—C251.381 (5)C37—H37C0.9600
C24—H240.9300P1—Pd12.3458 (6)
C25—C261.390 (4)Cl1—Pd12.3048 (7)
C25—H250.9300Pd1—Cl1i2.3048 (7)
C26—O11.363 (4)Pd1—P1i2.3458 (6)
C16—C11—C12117.9 (3)H27A—C27—H27C109.5
C16—C11—P1123.6 (2)H27B—C27—H27C109.5
C12—C11—P1118.5 (2)C32—C31—C36119.0 (3)
C13—C12—C11120.9 (3)C32—C31—P1124.0 (3)
C13—C12—H12119.6C36—C31—P1116.9 (2)
C11—C12—H12119.6C31—C32—C33120.0 (3)
C14—C13—C12120.1 (3)C31—C32—H32120.0
C14—C13—H13119.9C33—C32—H32120.0
C12—C13—H13119.9C34—C33—C32119.6 (4)
C15—C14—C13119.6 (3)C34—C33—H33120.2
C15—C14—H14120.2C32—C33—H33120.2
C13—C14—H14120.2C35—C34—C33121.6 (4)
C14—C15—C16120.6 (3)C35—C34—H34119.2
C14—C15—H15119.7C33—C34—H34119.2
C16—C15—H15119.7C34—C35—C36119.5 (4)
C15—C16—C11120.9 (3)C34—C35—H35120.3
C15—C16—H16119.5C36—C35—H35120.3
C11—C16—H16119.5O2—C36—C35124.8 (3)
C22—C21—C26118.1 (3)O2—C36—C31114.9 (3)
C22—C21—P1118.9 (2)C35—C36—C31120.3 (3)
C26—C21—P1122.9 (2)O2—C37—H37A109.5
C23—C22—C21121.8 (3)O2—C37—H37B109.5
C23—C22—H22119.1H37A—C37—H37B109.5
C21—C22—H22119.1O2—C37—H37C109.5
C24—C23—C22118.9 (3)H37A—C37—H37C109.5
C24—C23—H23120.6H37B—C37—H37C109.5
C22—C23—H23120.6C26—O1—C27119.1 (3)
C23—C24—C25121.6 (3)C36—O2—C37119.2 (3)
C23—C24—H24119.2C21—P1—C31108.64 (14)
C25—C24—H24119.2C21—P1—C11103.58 (12)
C24—C25—C26119.7 (3)C31—P1—C11104.58 (13)
C24—C25—H25120.2C21—P1—Pd1108.91 (9)
C26—C25—H25120.2C31—P1—Pd1111.13 (9)
O1—C26—C25123.7 (3)C11—P1—Pd1119.37 (8)
O1—C26—C21116.2 (3)Cl1—Pd1—Cl1i180.00 (4)
C25—C26—C21120.0 (3)Cl1—Pd1—P1i86.76 (2)
O1—C27—H27A109.5Cl1i—Pd1—P1i93.24 (2)
O1—C27—H27B109.5Cl1—Pd1—P193.24 (2)
H27A—C27—H27B109.5Cl1i—Pd1—P186.76 (2)
O1—C27—H27C109.5P1i—Pd1—P1180.00 (5)
C16—C11—C12—C130.2 (4)P1—C31—C36—C35−177.1 (3)
P1—C11—C12—C13178.3 (2)C25—C26—O1—C27−11.5 (5)
C11—C12—C13—C14−0.9 (4)C21—C26—O1—C27169.7 (3)
C12—C13—C14—C150.2 (5)C35—C36—O2—C37−12.9 (5)
C13—C14—C15—C161.2 (5)C31—C36—O2—C37167.9 (3)
C14—C15—C16—C11−1.9 (5)C22—C21—P1—C31−117.1 (2)
C12—C11—C16—C151.1 (4)C26—C21—P1—C3167.9 (3)
P1—C11—C16—C15−176.8 (2)C22—C21—P1—C11132.1 (2)
C26—C21—C22—C23−1.0 (5)C26—C21—P1—C11−42.9 (3)
P1—C21—C22—C23−176.2 (3)C22—C21—P1—Pd14.1 (3)
C21—C22—C23—C241.2 (5)C26—C21—P1—Pd1−170.9 (2)
C22—C23—C24—C25−0.5 (6)C32—C31—P1—C21−2.3 (3)
C23—C24—C25—C26−0.4 (6)C36—C31—P1—C21175.8 (2)
C24—C25—C26—O1−178.1 (3)C32—C31—P1—C11107.8 (3)
C24—C25—C26—C210.6 (5)C36—C31—P1—C11−74.1 (2)
C22—C21—C26—O1178.9 (3)C32—C31—P1—Pd1−122.1 (2)
P1—C21—C26—O1−6.1 (4)C36—C31—P1—Pd156.0 (2)
C22—C21—C26—C250.0 (5)C16—C11—P1—C21119.4 (2)
P1—C21—C26—C25175.0 (3)C12—C11—P1—C21−58.5 (2)
C36—C31—C32—C33−0.5 (5)C16—C11—P1—C315.7 (3)
P1—C31—C32—C33177.5 (2)C12—C11—P1—C31−172.3 (2)
C31—C32—C33—C34−0.7 (5)C16—C11—P1—Pd1−119.4 (2)
C32—C33—C34—C351.4 (6)C12—C11—P1—Pd162.7 (2)
C33—C34—C35—C36−0.9 (6)C21—P1—Pd1—Cl1103.82 (10)
C34—C35—C36—O2−179.6 (3)C31—P1—Pd1—Cl1−136.53 (11)
C34—C35—C36—C31−0.3 (6)C11—P1—Pd1—Cl1−14.71 (10)
C32—C31—C36—O2−179.7 (3)C21—P1—Pd1—Cl1i−76.18 (10)
P1—C31—C36—O22.2 (4)C31—P1—Pd1—Cl1i43.47 (11)
C32—C31—C36—C351.0 (5)C11—P1—Pd1—Cl1i165.29 (10)
P1—Pd12.3458 (6)
Cl1—Pd12.3048 (7)
Cl1—Pd1—P193.24 (2)
Cl1i—Pd1—P186.76 (2)

Symmetry code: (i) .

  3 in total

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Authors:  D Bradley G Williams; Megan L Shaw; Michael J Green; Cedric W Holzapfel
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Alcoholysis of acylpalladium(II) complexes relevant to the alternating copolymerization of ethene and carbon monoxide and the alkoxycarbonylation of alkenes: the importance of Cis-coordinating phosphines.

Authors:  Piet W N M van Leeuwen; Martin A Zuideveld; Bert H G Swennenhuis; Zoraida Freixa; Paul C J Kamer; Kees Goubitz; Jan Fraanje; Martin Lutz; Anthony L Spek
Journal:  J Am Chem Soc       Date:  2003-05-07       Impact factor: 15.419
  3 in total

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