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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m321.
Published online 2010 February 24. doi:  10.1107/S1600536810006471
PMCID: PMC2983618

cis-Dichloridobis(dimethoxy­phenyl­phosphine)palladium(II)

Abstract

The title compound, [PdCl2(C8H11O2P)2], has a comparable structure to those of related palladium dichloride complexes containing trimethyl phosphinite and methyl diphenyl phosphinite. The Pd atom is located on a crystallographic twofold rotation axis: thus, there is just one half-mol­ecule in the asymmetric unit. The structure is isomorphous with the platinum analogue cis-[PtCl2{P(OMe)2Ph}2].

Related literature

For related structures, see: Slawin et al. (2009 [triangle], 2007 [triangle]); Powell & Jacobson (1980 [triangle]). For preparation of the title compound, see: Jenkins & Shaw (1966 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m321-scheme1.jpg

Experimental

Crystal data

  • [PdCl2(C8H11O2P)2]
  • M r = 517.60
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m321-efi1.jpg
  • a = 10.876 (7) Å
  • b = 9.174 (5) Å
  • c = 20.722 (13) Å
  • β = 102.196 (7)°
  • V = 2021 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.36 mm−1
  • T = 125 K
  • 0.16 × 0.15 × 0.09 mm

Data collection

  • Rigaku Mercury CCD diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.812, T max = 0.888
  • 8406 measured reflections
  • 1775 independent reflections
  • 1653 reflections with F 2 > 2σ(F 2)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.050
  • S = 1.09
  • 1775 reflections
  • 117 parameters
  • All H-atom parameters refined
  • Δρmax = 1.15 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: SCXmini (Rigaku/MSC, 2006 [triangle]); cell refinement: PROCESS-AUTO (Rigaku, 1998 [triangle]); data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: CrystalStructure (Rigaku/MSC, 2006 [triangle]); software used to prepare material for publication: CrystalStructure.

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006471/bt5195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006471/bt5195Isup2.hkl

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

supplementary crystallographic information

Experimental

Based on the method of Jenkins & Shaw (1966). To (0.3 g (0.93 mmol) of potassium tetrachloropalladate was dissolved in 10 ml e thanol and 0.147 ml (1.86 mmol) of P(OMe)2Ph was added. The solution was stirred at room temperature for 30 min s before being filtered and then precipitated by slow addition of hexane to give a white crystalline solid. Crystals were grown for X-ray crystallography via slow diffusion of hexane into a solution of the product in dichloromethane [cis-PdCl2(P(OMe)2Ph)2] (0.40 mmol, ca. 68 %). 31P-{1H} NMR: δ 125.8 ppm.

Refinement

All H atoms were included in calculated positions (C—H distances are 0.96 Å for methyl H atoms, 0.93 Å for aromatic H atoms) and were refined as riding atoms with Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). The highest peak in the difference map is 1.23 Å from atom Pd1.

Figures

Fig. 1.
The structure of the title compound with displacement ellipsoids drawn at the 50% probability level, hydrogen atoms omitted for clarity. Symmetry operator for generating equivalent atoms (A): -x, y, 1.5-z.

Crystal data

[PdCl2(C8H11O2P)2]F(000) = 1040.00
Mr = 517.60Dx = 1.701 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2ycCell parameters from 2591 reflections
a = 10.876 (7) Åθ = 2.9–25.4°
b = 9.174 (5) ŵ = 1.36 mm1
c = 20.722 (13) ÅT = 125 K
β = 102.196 (7)°Prism, colorless
V = 2021 (2) Å30.16 × 0.15 × 0.09 mm
Z = 4

Data collection

Rigaku Mercury CCD diffractometer1653 reflections with F2 > 2σ(F2)
Detector resolution: 0.83 pixels mm-1Rint = 0.032
ω scansθmax = 25.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −13→13
Tmin = 0.812, Tmax = 0.888k = −11→11
8406 measured reflectionsl = −24→24
1775 independent reflections

Refinement

Refinement on F2All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.023w = 1/[σ2(Fo2) + (0.0162P)2 + 4.843P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.050(Δ/σ)max = 0.001
S = 1.09Δρmax = 1.15 e Å3
1775 reflectionsΔρmin = −0.32 e Å3
117 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Pd10.00000.09671 (3)0.75000.01397 (8)
Cl1−0.09211 (6)−0.08216 (6)0.67365 (3)0.02090 (14)
P10.10038 (6)0.25152 (7)0.82618 (3)0.01521 (14)
O10.24303 (15)0.21038 (18)0.85487 (8)0.0189 (3)
O20.10272 (16)0.41579 (17)0.80284 (8)0.0199 (3)
C10.0398 (2)0.2542 (2)0.90033 (12)0.0172 (5)
C20.0988 (2)0.1823 (2)0.95758 (12)0.0220 (5)
C30.0459 (2)0.1856 (3)1.01266 (13)0.0285 (6)
C4−0.0648 (2)0.2601 (3)1.01080 (13)0.0302 (6)
C5−0.1248 (2)0.3298 (3)0.95385 (14)0.0328 (6)
C6−0.0733 (2)0.3264 (2)0.89844 (13)0.0259 (5)
C70.3242 (2)0.1770 (3)0.80984 (14)0.0278 (6)
C80.1786 (2)0.5209 (2)0.84682 (13)0.0274 (6)
H10.29930.08580.78830.033*
H20.17360.13210.95880.026*
H30.08510.13761.05100.034*
H4−0.09940.26341.04820.036*
H5−0.19990.37910.95280.039*
H6−0.11430.37240.85990.031*
H70.40970.17040.83400.033*
H80.31750.25280.77730.033*
H90.16970.50380.89130.033*
H100.15080.61790.83370.033*
H110.26540.51030.84440.033*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pd10.01670 (15)0.01215 (14)0.01241 (14)0.00000.00162 (10)0.0000
Cl10.0256 (3)0.0154 (3)0.0190 (3)−0.0012 (2)−0.0014 (2)−0.0041 (2)
P10.0170 (3)0.0143 (3)0.0137 (3)−0.0012 (2)0.0020 (2)0.0000 (2)
O10.0154 (8)0.0217 (8)0.0194 (8)−0.0021 (7)0.0029 (6)−0.0027 (7)
O20.0266 (9)0.0151 (8)0.0163 (8)−0.0040 (6)0.0002 (7)0.0006 (6)
C10.0198 (12)0.0159 (12)0.0159 (11)−0.0031 (9)0.0037 (9)−0.0022 (9)
C20.0212 (13)0.0248 (14)0.0188 (12)0.0032 (10)0.0017 (10)−0.0012 (10)
C30.0336 (15)0.0356 (16)0.0153 (13)−0.0020 (12)0.0025 (11)0.0020 (11)
C40.0363 (16)0.0370 (16)0.0203 (14)−0.0054 (12)0.0125 (12)−0.0051 (12)
C50.0279 (15)0.0383 (17)0.0352 (16)0.0073 (12)0.0132 (12)0.0003 (13)
C60.0265 (14)0.0271 (14)0.0245 (14)0.0048 (11)0.0062 (11)0.0048 (11)
C70.0239 (14)0.0317 (15)0.0308 (15)−0.0024 (11)0.0127 (11)−0.0017 (12)
C80.0387 (16)0.0172 (13)0.0249 (14)−0.0079 (11)0.0034 (12)−0.0043 (11)

Geometric parameters (Å, °)

Pd1—Cl12.3515 (16)C4—C51.379 (3)
Pd1—Cl1i2.3515 (16)C5—C61.380 (4)
Pd1—P12.2300 (16)C2—H20.930
Pd1—P1i2.2300 (16)C3—H30.930
P1—O11.5853 (16)C4—H40.930
P1—O21.5846 (17)C5—H50.930
P1—C11.795 (2)C6—H60.930
O1—C71.446 (3)C7—H10.960
O2—C81.458 (2)C7—H70.960
C1—C21.390 (3)C7—H80.960
C1—C61.391 (3)C8—H90.960
C2—C31.383 (4)C8—H100.960
C3—C41.378 (4)C8—H110.960
O1···C3ii3.324 (2)H3···H9ii2.979
O2···C7iii3.551 (3)H3···H11ii2.774
C3···O1ii3.324 (2)H4···Cl1xiv3.073
C3···C3iv3.557 (3)H4···C5xii3.112
C7···O2v3.551 (3)H4···C8xiii3.191
C7···C8v3.542 (3)H4···H4xii3.467
C8···C7iii3.542 (3)H4···H5xii2.542
Cl1···H3vi3.536H4···H7ii2.908
Cl1···H4vi3.073H4···H9xiii2.669
Cl1···H5vii3.099H4···H10xiii2.840
Cl1···H6vii3.149H5···Cl1xv3.099
Cl1···H7v3.041H5···C2xi3.554
Cl1···H8viii2.961H5···C4xii3.093
Cl1···H8v3.311H5···C5xii3.552
Cl1···H10ix2.822H5···H2xi2.715
O1···H3ii2.775H5···H4xii2.542
O1···H6x3.459H5···H5xii3.396
O2···H1iii2.826H5···H9xiii3.354
O2···H7xi3.294H5···H10viii3.575
C2···H2ii3.196H6···Cl1xv3.149
C2···H3iv3.535H6···O1xi3.459
C2···H5x3.554H6···C7xi3.007
C3···H2ii3.419H6···H1xi2.515
C3···H3iv3.431H6···H7xi2.809
C3···H7ii3.381H6···H10viii3.418
C4···H5xii3.093H6···H11viii3.560
C4···H7ii3.363H7···Cl1iii3.041
C4···H9xiii3.329H7···O2x3.294
C5···H2xi3.551H7···C3ii3.381
C5···H4xii3.112H7···C4ii3.363
C5···H5xii3.552H7···C6x3.417
C6···H1xi3.384H7···C8x3.190
C6···H7xi3.417H7···H3ii2.955
C6···H10viii3.572H7···H4ii2.908
C6···H11viii3.451H7···H6x2.809
C7···H3ii3.313H7···H9x3.213
C7···H6x3.007H7···H10x2.668
C7···H10x3.523H7···H10v3.431
C7···H10v3.092H8···Cl1xvi2.961
C7···H11v3.491H8···Cl1iii3.311
C8···H1iii2.922H8···C8v3.345
C8···H3ii3.301H8···H1iii3.474
C8···H4xiii3.191H8···H10v2.698
C8···H7xi3.190H8···H11v3.341
C8···H8iii3.345H9···C4xiii3.329
H1···O2v2.826H9···H2ii3.445
H1···C6x3.384H9···H3ii2.979
H1···C8v2.922H9···H4xiii2.669
H1···H6x2.515H9···H5xiii3.354
H1···H8v3.474H9···H7xi3.213
H1···H10v2.712H10···Cl1xvii2.822
H1···H11v2.779H10···C6xvi3.572
H2···C2ii3.196H10···C7xi3.523
H2···C3ii3.419H10···C7iii3.092
H2···C5x3.551H10···H1iii2.712
H2···H2ii3.026H10···H4xiii2.840
H2···H3ii3.409H10···H5xvi3.575
H2···H5x2.715H10···H6xvi3.418
H2···H9ii3.445H10···H7xi2.668
H3···Cl1xiv3.536H10···H7iii3.431
H3···O1ii2.775H10···H8iii2.698
H3···C2iv3.535H11···C6xvi3.451
H3···C3iv3.431H11···C7iii3.491
H3···C7ii3.313H11···H1iii2.779
H3···C8ii3.301H11···H3ii2.774
H3···H2ii3.409H11···H6xvi3.560
H3···H3iv3.552H11···H8iii3.341
H3···H7ii2.955
Cl1—Pd1—Cl1i91.49 (2)C1—C2—H2120.1
Cl1—Pd1—P1174.86 (2)C3—C2—H2120.1
Cl1—Pd1—P1i83.85 (2)C2—C3—H3120.0
Cl1i—Pd1—P183.85 (2)C4—C3—H3120.0
Cl1i—Pd1—P1i174.86 (2)C3—C4—H4119.8
P1—Pd1—P1i100.88 (2)C5—C4—H4119.8
Pd1—P1—O1114.07 (6)C4—C5—H5120.0
Pd1—P1—O2115.26 (6)C6—C5—H5120.0
Pd1—P1—C1113.66 (7)C1—C6—H6120.0
O1—P1—O2105.27 (9)C5—C6—H6120.0
O1—P1—C1100.91 (10)O1—C7—H1109.5
O2—P1—C1106.30 (10)O1—C7—H7109.5
P1—O1—C7119.39 (14)O1—C7—H8109.5
P1—O2—C8118.82 (14)H1—C7—H7109.5
P1—C1—C2122.50 (19)H1—C7—H8109.5
P1—C1—C6117.70 (18)H7—C7—H8109.5
C2—C1—C6119.7 (2)O2—C8—H9109.5
C1—C2—C3119.8 (2)O2—C8—H10109.5
C2—C3—C4120.1 (2)O2—C8—H11109.5
C3—C4—C5120.4 (2)H9—C8—H10109.5
C4—C5—C6120.0 (2)H9—C8—H11109.5
C1—C6—C5119.9 (2)H10—C8—H11109.5
Cl1—Pd1—P1i—O1i47.02 (7)O1—P1—O2—C8−46.3 (2)
Cl1—Pd1—P1i—O2i169.01 (8)O2—P1—O1—C7−77.89 (18)
Cl1—Pd1—P1i—C1i−67.93 (8)O1—P1—C1—C2−21.0 (2)
Cl1i—Pd1—P1—O147.02 (7)O1—P1—C1—C6161.81 (18)
Cl1i—Pd1—P1—O2169.01 (8)C1—P1—O1—C7171.69 (17)
Cl1i—Pd1—P1—C1−67.93 (8)O2—P1—C1—C2−130.59 (19)
P1—Pd1—P1i—O1i−135.01 (7)O2—P1—C1—C652.2 (2)
P1—Pd1—P1i—O2i−13.03 (8)C1—P1—O2—C860.2 (2)
P1—Pd1—P1i—C1i110.03 (8)P1—C1—C2—C3−178.50 (19)
P1i—Pd1—P1—O1−135.01 (7)P1—C1—C6—C5179.1 (2)
P1i—Pd1—P1—O2−13.03 (8)C2—C1—C6—C51.8 (3)
P1i—Pd1—P1—C1110.03 (8)C6—C1—C2—C3−1.3 (3)
Pd1—P1—O1—C749.44 (18)C1—C2—C3—C4−0.1 (3)
Pd1—P1—O2—C8−172.89 (16)C2—C3—C4—C51.0 (4)
Pd1—P1—C1—C2101.57 (19)C3—C4—C5—C6−0.6 (4)
Pd1—P1—C1—C6−75.6 (2)C4—C5—C6—C1−0.8 (4)

Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1/2, −y+1/2, −z+2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x, −y, −z+2; (v) −x+1/2, y−1/2, −z+3/2; (vi) x, −y, z−1/2; (vii) −x−1/2, y−1/2, −z+3/2; (viii) x−1/2, y−1/2, z; (ix) −x, y−1, −z+3/2; (x) x+1/2, y−1/2, z; (xi) x−1/2, y+1/2, z; (xii) −x−1/2, −y+1/2, −z+2; (xiii) −x, −y+1, −z+2; (xiv) x, −y, z+1/2; (xv) −x−1/2, y+1/2, −z+3/2; (xvi) x+1/2, y+1/2, z; (xvii) −x, y+1, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5195).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Jenkins, J. M. & Shaw, B. L. (1966). J. Chem. Soc. A, pp. 770–774.
  • Powell, D. R. & Jacobson, R. A. (1980). Cryst. Struct. Commun.9, 1023–1027.
  • Rigaku (1998). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2006). CrystalStructure and SCXmini Benchtop Crystallography System Software Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Slawin, A. M. Z., Waddell, P. G. & Woollins, J. D. (2007). Acta Cryst. E63, m2017.
  • Slawin, A. M. Z., Waddell, P. G. & Woollins, J. D. (2009). Acta Cryst. E65, m1391. [PMC free article] [PubMed]

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