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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m57–m58.
Published online 2008 December 13. doi:  10.1107/S1600536808041615
PMCID: PMC2967900

Chlorido{[2-(dicyclo­hexyl­phosphano­yl)eth­yl]bis­[2-(dicyclo­hexyl­phosphan­yl)eth­yl]phosphane}platinum(II) chloride dichloro­methane hemisolvate tetra­hydrate

Abstract

The title compound, [PtCl(C42H78OP4)]Cl·0.5CH2Cl2·4H2O, crystallizes as a contact ion-pair with two close inter­molecular C—H(...)Cl contacts between CH acidic αH atoms of the phosphane ligand and the chloride anion. A chloride ligand together with three coordinating P ligand atoms create a slightly distorted square-planar coordination environment around the PtII center. An inter­molecular water O—H(...)Cl and water O—H(...)OP hydrogen-bond network completes the coordination around the anion. In addition, a disordered CH2Cl2 solvent mol­ecule cocrystallized within a hydro­phobic cavity spanned by the dicyclo­hexyl­phosphane ligands.

Related literature

For related literature on PtII complexes, see: Brüggeller et al. (1992 [triangle]). For the structure of a related phosphane PtII complex with pendant P=O groups, see: Rieckborn et al. (2008 [triangle]). For selective activation of mol­ecular oxygen by platinum complexes, see: Aizawa et al. (2005 [triangle]); Poverenov et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-00m57-scheme1.jpg

Experimental

Crystal data

  • [PtCl(C42H78OP4)]Cl·0.5CH2Cl2·4H2O
  • M r = 1103.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m57-efi1.jpg
  • a = 20.3023 (18) Å
  • b = 28.077 (3) Å
  • c = 17.9581 (15) Å
  • β = 101.292 (2)°
  • V = 10038.6 (15) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.12 mm−1
  • T = 100 (2) K
  • 0.48 × 0.10 × 0.07 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.694, T max = 0.804
  • 33754 measured reflections
  • 11635 independent reflections
  • 7471 reflections with I > 2σ(I)
  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.063
  • S = 0.76
  • 11635 reflections
  • 544 parameters
  • 18 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.86 e Å−3
  • Δρmin = −1.61 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041615/lh2731sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041615/lh2731Isup2.hkl

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

Acknowledgments

Financial support by the Deutsche Forschungsgemeinschaft (DFG), grant No. PR 654/1–1, is gratefully acknowledged. TPR thanks the Studienstiftung des deutschen Volkes for a fellowship.

supplementary crystallographic information

Comment

Selective activation of molecular oxygen by platinum complexes is an active field of current research (Aizawa et al. 2005; Poverenov et al. 2008). PlatinumII complexes with pendant phosphane ligands are able to activate molecular oxygen revealing an oxidized phosphane group (Aizawa et al. 2005; Rieckborn et al. 2008). The title compund, [Pt(Cl)(C42H76OP4)]+ Cl- * 4 H2O * 0.5 CH2Cl2 consists of a platinum(II) phosphane complex cation which crystallizes with a chloride anion as a contact ion pair including short CH···Cl contacts (2.72 Å and 2.92 Å). Further structural parameters are listed in Table 2. In addition four water molecules are connected via O–H···Cl2 (2.40 Å and 2.43 Å) bridges to the anion and via O–H···O=P (1.94 Å) bridges to the phosphane oxide group of the complex cation (Figure 1). The PtII centre is tetracoordinated revealing a slightly distorted square-planar coordination geometry (Brüggeller et al., 1992). The phosphane oxide group of the ligand is not coordinated to the PtII centre in the solid state (Rieckborn et al., 2008).

Experimental

Unless otherwise stated all reactions were conducted under Schlenk techniques. Solvents were dried and stored under nitrogen.

Potassium tetrachloroplatinate(II) (215 mg, 0.52 mmol), was dissolved in 30 ml water and 30 ml e thanol was added. 367 mg (0.52 mmol) of Tris(2-(dicyclohexylphosphino)-ethyl)phosphane was dissolved in 15 ml dichloromethane and added to the reaction mixture. The colourless suspension was stirred at room temperature for 3 days. Afterwards the mixture was concentrated to small volume and a colourless solid precipitated. The precipitate was filtered and dried in vacuo. Single crystals were received by diffusion of n-hexane into a solution of the product in dichloromethane in air.

Refinement

All non-hydrogen atoms were refined with anisotropic temperature parameters and H atoms were refined using a riding model with C—H distances set to 0.99 Å for aliphatic, and 0.80 Å for water O—H bonds. Uiso(H) values were set to 1.2 U~eq~ for carbon bonded and to 1.5 U~eq~ for oxygen bonded H atoms of the parent atom. The dichloromethane molecule has been refined using half of a molecule of dichloromethane disordered over two sites with relative occupancies of s.o.f. 0.30 with the dichloromethane molecule lying on a twofold symmetry axis and the other dichloromethane molecule disordered close to the twofold rotation axis (s.o.f. 0.35). Thus, this site is occupied by one dichloromethane molecule. For the bonds C99—Cl4 and C99—Cl5 distances of 1.77 (1) were applied.

Figures

Fig. 1.
Representation of the Pt(II) complex with displacement ellipsoids at 50% probability. H atoms of the cyclohexyl and ethylene groups have been omitted for clarity. The hydrogen bonds between the anion and water molecules and the C—H groups respectively ...

Crystal data

[PtCl(C42H78OP4)]Cl·0.5CH2Cl2·4H2OF(000) = 4560
Mr = 1103.39Dx = 1.459 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4947 reflections
a = 20.3023 (18) Åθ = 2.3–23.8°
b = 28.077 (3) ŵ = 3.12 mm1
c = 17.9581 (15) ÅT = 100 K
β = 101.292 (2)°Needle, colourless
V = 10038.6 (15) Å30.48 × 0.1 × 0.07 mm
Z = 8

Data collection

Bruker SMART APEX CCD area-detector diffractometer11635 independent reflections
Radiation source: fine-focus sealed tube7471 reflections with I > 2σ(I)
graphiteRint = 0.061
[var phi] and ω scansθmax = 28.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −26→25
Tmin = 0.694, Tmax = 0.804k = −20→37
33754 measured reflectionsl = −23→20

Refinement

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) = 0.063H atoms treated by a mixture of independent and constrained refinement
S = 0.76w = 1/[σ2(Fo2) + (0.0136P)2 + 2P] where P = (Fo2 + 2Fc2)/3
11635 reflections(Δ/σ)max = 0.003
544 parametersΔρmax = 1.86 e Å3
18 restraintsΔρmin = −1.61 e Å3

Special details

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.

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

xyzUiso*/UeqOcc. (<1)
Pt10.297423 (8)0.640641 (7)0.845227 (9)0.01690 (5)
P10.35938 (6)0.57558 (4)0.85196 (6)0.0177 (3)
P20.30418 (5)0.64073 (5)0.71803 (6)0.0200 (3)
P30.31646 (5)0.63818 (5)0.97692 (6)0.0179 (2)
P40.21292 (6)0.45580 (5)0.81651 (7)0.0235 (3)
Cl10.23492 (6)0.71189 (4)0.83402 (6)0.0275 (3)
Cl20.47682 (6)0.45429 (5)0.88578 (6)0.0343 (3)
O10.18711 (14)0.46476 (11)0.73396 (15)0.0286 (8)
C10.4140 (2)0.58277 (16)0.7839 (2)0.0211 (10)
H1B0.44800.60770.80150.025*
H1C0.43760.55250.77840.025*
C20.3701 (2)0.59722 (16)0.7074 (2)0.0220 (11)
H2A0.34850.56840.68180.026*
H2B0.39900.61110.67470.026*
C30.4059 (2)0.56782 (16)0.9477 (2)0.0206 (11)
H3A0.41930.53400.95590.025*
H3B0.44720.58740.95530.025*
C40.3630 (2)0.58266 (15)1.0055 (2)0.0181 (10)
H4A0.39240.58721.05580.022*
H4B0.33070.55691.01010.022*
C50.3191 (2)0.51863 (15)0.8243 (2)0.0193 (10)
H5A0.30360.51850.76850.023*
H5B0.35310.49310.83710.023*
C60.2592 (2)0.50651 (16)0.8612 (2)0.0226 (11)
H6A0.22880.53440.85730.027*
H6B0.27560.49960.91570.027*
C70.2295 (2)0.62466 (16)0.6469 (2)0.0218 (11)
H7A0.24490.61760.59850.026*
C80.1788 (2)0.66504 (17)0.6306 (2)0.0280 (12)
H8A0.20040.69330.61260.034*
H8B0.16370.67390.67790.034*
C90.1176 (2)0.65002 (17)0.5697 (2)0.0323 (13)
H9A0.08400.67600.56250.039*
H9B0.13210.64490.52080.039*
C100.0854 (2)0.60483 (18)0.5921 (3)0.0345 (13)
H10A0.04880.59490.54990.041*
H10B0.06530.61130.63710.041*
C110.1364 (2)0.56447 (17)0.6103 (2)0.0309 (12)
H11A0.11470.53660.62920.037*
H11B0.15160.55480.56340.037*
C120.1964 (2)0.57966 (17)0.6696 (2)0.0246 (11)
H12A0.22990.55350.67760.030*
H12B0.18180.58530.71840.030*
C130.3309 (2)0.69867 (16)0.6890 (2)0.0211 (10)
H13A0.29320.72120.69140.025*
C140.3418 (2)0.70027 (17)0.6068 (2)0.0304 (12)
H14A0.37830.67800.60130.036*
H14B0.30030.68960.57210.036*
C150.3600 (2)0.75041 (18)0.5843 (3)0.0365 (13)
H15A0.36960.74960.53230.044*
H15B0.32130.77190.58390.044*
C160.4207 (2)0.76959 (18)0.6388 (3)0.0392 (14)
H16A0.42970.80270.62470.047*
H16B0.46060.75000.63560.047*
C170.4080 (2)0.76847 (17)0.7204 (3)0.0350 (13)
H17A0.44810.78060.75560.042*
H17B0.36970.78960.72400.042*
C180.3925 (2)0.71831 (16)0.7436 (2)0.0274 (12)
H18A0.38380.71870.79590.033*
H18B0.43170.69740.74290.033*
C190.24466 (19)0.63714 (16)1.0238 (2)0.0188 (9)
H19A0.26130.62681.07740.023*
C200.1922 (2)0.60065 (16)0.9864 (2)0.0240 (11)
H20A0.17570.60960.93270.029*
H20B0.21340.56890.98740.029*
C210.1331 (2)0.59805 (17)1.0269 (3)0.0285 (12)
H21A0.09920.57550.99970.034*
H21B0.14880.58571.07900.034*
C220.1008 (2)0.64619 (17)1.0309 (2)0.0282 (11)
H22A0.06440.64351.06020.034*
H22B0.08070.65710.97900.034*
C230.1522 (2)0.68244 (16)1.0686 (2)0.0222 (11)
H23A0.16970.67291.12190.027*
H23B0.13050.71401.06900.027*
C240.2105 (2)0.68604 (15)1.0261 (2)0.0187 (10)
H24A0.24380.70951.05180.022*
H24B0.19350.69730.97360.022*
C250.3718 (2)0.68629 (15)1.0232 (2)0.0179 (10)
H25A0.34940.71721.00600.021*
C260.3821 (2)0.68514 (16)1.1102 (2)0.0236 (11)
H26A0.33800.68731.12570.028*
H26B0.40330.65461.12930.028*
C270.4265 (2)0.72639 (18)1.1448 (2)0.0313 (13)
H27A0.40360.75691.12850.038*
H27B0.43340.72461.20080.038*
C280.4940 (2)0.72543 (18)1.1210 (2)0.0293 (12)
H28A0.52110.75311.14320.035*
H28B0.51850.69611.14060.035*
C290.4853 (2)0.72684 (16)1.0354 (2)0.0268 (12)
H29A0.52980.72431.02090.032*
H29B0.46520.75771.01630.032*
C300.4402 (2)0.68627 (17)0.9986 (2)0.0260 (11)
H30A0.46300.65551.01280.031*
H30B0.43300.68940.94270.031*
C310.1451 (2)0.44705 (17)0.8681 (2)0.0283 (12)
H31A0.16510.43760.92140.034*
C320.0976 (2)0.40718 (17)0.8315 (3)0.0326 (12)
H32A0.08470.41320.77620.039*
H32B0.12190.37640.83870.039*
C330.0344 (2)0.40347 (18)0.8646 (3)0.0312 (12)
H33A0.00380.38000.83470.037*
H33B0.04670.39140.91730.037*
C34−0.0026 (2)0.45034 (18)0.8652 (3)0.0346 (13)
H34A−0.04110.44610.89090.042*
H34B−0.02020.46070.81240.042*
C350.0443 (2)0.48812 (18)0.9063 (3)0.0381 (14)
H35A0.05880.47900.96030.046*
H35B0.02020.51890.90430.046*
C360.1059 (2)0.49382 (18)0.8701 (3)0.0354 (13)
H36A0.13620.51790.89900.042*
H36B0.09140.50580.81760.042*
C370.2716 (2)0.40533 (16)0.8290 (2)0.0253 (11)
H37A0.31380.41790.81530.030*
C380.2927 (3)0.38674 (19)0.9104 (3)0.0433 (15)
H38A0.30950.41350.94480.052*
H38B0.25330.37270.92720.052*
C390.3478 (2)0.34906 (18)0.9143 (3)0.0403 (15)
H39A0.38810.36370.90050.048*
H39B0.36040.33690.96690.048*
C400.3242 (2)0.30842 (17)0.8613 (3)0.0388 (14)
H40A0.28540.29260.87680.047*
H40B0.36070.28470.86430.047*
C410.3038 (3)0.32640 (19)0.7802 (3)0.0386 (14)
H41A0.28680.29950.74630.046*
H41B0.34360.33980.76340.046*
C420.2498 (2)0.36445 (18)0.7741 (3)0.0355 (13)
H42A0.20820.35010.78520.043*
H42B0.23960.37690.72160.043*
O30.57043 (15)0.54710 (12)0.94855 (17)0.0400 (10)
H3C0.5603 (4)0.54853 (12)0.9894 (14)0.060*
H3D0.5423 (10)0.5255 (7)0.9247 (8)0.060*
O40.71140 (15)0.53269 (11)0.95654 (15)0.0364 (10)
H4D0.7156 (2)0.5065 (10)0.9274 (11)0.055*
H4C0.6772 (12)0.5408 (3)0.9514 (3)0.055*
O50.27701 (15)0.45872 (11)0.63870 (16)0.0354 (10)
H5C0.2514 (9)0.46011 (12)0.6665 (10)0.053*
H5D0.3138 (13)0.4488 (4)0.6669 (10)0.053*
O60.4078 (2)0.4460 (3)0.7120 (2)0.102 (2)
H6C0.426 (3)0.438 (3)0.7536 (19)0.154*
H6D0.437 (3)0.450 (3)0.688 (4)0.154*
Cl40.0446 (9)0.6580 (5)0.7868 (11)0.136 (6)0.347 (6)
Cl5−0.0603 (3)0.5963 (3)0.7014 (4)0.054 (2)0.347 (6)
C99−0.0324 (12)0.6561 (4)0.7228 (18)0.034 (7)0.347 (6)
H99A−0.02780.67240.67520.041*0.347 (6)
H99B−0.06660.67340.74470.041*0.347 (6)
C980.00000.5903 (11)0.75000.051 (9)0.306 (12)
H98A−0.030 (7)0.569 (4)0.773 (8)0.061*0.306 (12)
Cl5A−0.0622 (3)0.6260 (3)0.6985 (4)0.044 (3)0.306 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pt10.02001 (9)0.01445 (9)0.01693 (8)0.00236 (10)0.00529 (6)0.00098 (10)
P10.0186 (6)0.0153 (7)0.0196 (6)0.0014 (5)0.0052 (5)0.0007 (5)
P20.0236 (6)0.0191 (6)0.0188 (6)0.0007 (6)0.0076 (5)0.0005 (6)
P30.0214 (6)0.0158 (6)0.0174 (5)0.0019 (6)0.0059 (5)0.0006 (6)
P40.0230 (7)0.0222 (7)0.0259 (7)−0.0038 (6)0.0066 (5)−0.0022 (6)
Cl10.0385 (7)0.0222 (7)0.0237 (6)0.0146 (6)0.0110 (5)0.0054 (5)
Cl20.0316 (7)0.0424 (9)0.0283 (7)0.0106 (6)0.0045 (5)−0.0028 (6)
O10.0274 (19)0.033 (2)0.0256 (17)−0.0057 (16)0.0056 (14)−0.0026 (16)
C10.022 (2)0.019 (3)0.023 (2)−0.001 (2)0.007 (2)−0.003 (2)
C20.024 (3)0.025 (3)0.020 (2)0.001 (2)0.012 (2)0.003 (2)
C30.020 (2)0.014 (3)0.028 (3)0.001 (2)0.006 (2)−0.001 (2)
C40.022 (2)0.013 (2)0.020 (2)0.004 (2)0.0045 (19)0.001 (2)
C50.022 (2)0.013 (2)0.023 (2)0.004 (2)0.0049 (19)−0.001 (2)
C60.025 (3)0.019 (3)0.023 (2)0.000 (2)0.004 (2)0.000 (2)
C70.025 (3)0.024 (3)0.018 (2)0.000 (2)0.0078 (19)0.002 (2)
C80.027 (3)0.026 (3)0.029 (3)0.003 (2)0.001 (2)0.002 (2)
C90.027 (3)0.032 (4)0.034 (3)0.010 (2)−0.003 (2)0.005 (3)
C100.025 (3)0.051 (4)0.026 (3)−0.001 (3)0.002 (2)0.002 (3)
C110.040 (3)0.026 (3)0.028 (3)−0.004 (3)0.009 (2)0.004 (2)
C120.019 (3)0.027 (3)0.027 (3)0.004 (2)0.001 (2)0.006 (2)
C130.024 (3)0.018 (3)0.023 (2)0.000 (2)0.010 (2)0.001 (2)
C140.037 (3)0.031 (3)0.027 (3)−0.001 (3)0.013 (2)0.004 (2)
C150.044 (3)0.032 (3)0.040 (3)0.004 (3)0.025 (3)0.012 (3)
C160.046 (4)0.025 (3)0.054 (3)−0.002 (3)0.027 (3)0.008 (3)
C170.032 (3)0.024 (3)0.051 (3)−0.004 (2)0.014 (3)−0.003 (3)
C180.031 (3)0.021 (3)0.034 (3)−0.002 (2)0.014 (2)0.004 (2)
C190.020 (2)0.020 (3)0.018 (2)0.003 (2)0.0057 (17)0.001 (2)
C200.032 (3)0.018 (3)0.024 (2)0.001 (2)0.010 (2)−0.002 (2)
C210.025 (3)0.028 (3)0.034 (3)−0.005 (2)0.009 (2)−0.009 (3)
C220.029 (3)0.027 (3)0.033 (3)0.001 (3)0.016 (2)−0.001 (3)
C230.026 (3)0.019 (3)0.024 (2)0.006 (2)0.011 (2)0.000 (2)
C240.020 (2)0.014 (2)0.023 (2)0.001 (2)0.0052 (19)0.002 (2)
C250.020 (2)0.015 (3)0.021 (2)0.001 (2)0.0079 (19)0.003 (2)
C260.027 (3)0.026 (3)0.018 (2)0.000 (2)0.005 (2)0.003 (2)
C270.033 (3)0.035 (3)0.024 (3)−0.001 (3)0.002 (2)−0.006 (2)
C280.026 (3)0.029 (3)0.032 (3)−0.003 (2)0.004 (2)−0.008 (2)
C290.018 (3)0.021 (3)0.042 (3)−0.006 (2)0.008 (2)−0.004 (2)
C300.025 (3)0.027 (3)0.026 (3)0.000 (2)0.006 (2)−0.001 (2)
C310.028 (3)0.030 (3)0.025 (3)−0.002 (2)0.002 (2)0.000 (2)
C320.034 (3)0.028 (3)0.036 (3)−0.008 (3)0.007 (2)−0.002 (3)
C330.022 (3)0.035 (3)0.036 (3)−0.007 (2)0.004 (2)0.004 (3)
C340.029 (3)0.044 (4)0.032 (3)−0.004 (3)0.008 (2)0.008 (3)
C350.030 (3)0.041 (4)0.046 (3)−0.001 (3)0.015 (2)−0.010 (3)
C360.033 (3)0.031 (3)0.045 (3)−0.007 (3)0.015 (2)−0.011 (3)
C370.027 (3)0.024 (3)0.025 (3)−0.007 (2)0.005 (2)−0.003 (2)
C380.061 (4)0.038 (4)0.031 (3)0.013 (3)0.010 (3)−0.001 (3)
C390.047 (3)0.045 (4)0.030 (3)0.017 (3)0.009 (2)0.002 (3)
C400.034 (3)0.018 (3)0.069 (4)0.003 (2)0.021 (3)0.003 (3)
C410.043 (3)0.035 (3)0.040 (3)−0.010 (3)0.013 (3)−0.018 (3)
C420.039 (3)0.030 (3)0.037 (3)−0.012 (3)0.003 (2)−0.006 (3)
O30.041 (2)0.041 (2)0.042 (2)0.0051 (19)0.0187 (17)0.0057 (19)
O40.043 (2)0.032 (2)0.036 (2)−0.0009 (18)0.0141 (16)−0.0039 (18)
O50.040 (2)0.039 (2)0.0301 (19)0.0009 (18)0.0133 (15)−0.0003 (18)
O60.036 (3)0.245 (7)0.027 (2)−0.003 (4)0.0055 (19)−0.010 (4)
Cl40.198 (13)0.106 (8)0.126 (10)−0.103 (8)0.089 (7)−0.088 (8)
Cl50.054 (4)0.065 (4)0.047 (3)−0.016 (4)0.020 (3)−0.018 (4)
C990.040 (9)0.034 (11)0.033 (10)−0.004 (8)0.020 (7)0.002 (8)
C980.051 (18)0.058 (19)0.040 (16)0.0000.000 (14)0.000
Cl5A0.037 (3)0.054 (7)0.037 (3)0.009 (5)−0.001 (2)0.013 (5)

Geometric parameters (Å, °)

Pt1—P12.2078 (12)C21—H21B0.9900
Pt1—P22.3151 (11)C22—C231.519 (6)
Pt1—P32.3215 (10)C22—H22A0.9900
Pt1—Cl12.3563 (11)C22—H22B0.9900
P1—C31.806 (4)C23—C241.532 (5)
P1—C11.815 (4)C23—H23A0.9900
P1—C51.820 (4)C23—H23B0.9900
P2—C131.823 (4)C24—H24A0.9900
P2—C71.838 (4)C24—H24B0.9900
P2—C21.849 (4)C25—C261.536 (5)
P3—C191.820 (4)C25—C301.536 (5)
P3—C41.842 (4)C25—H25A1.0000
P3—C251.847 (4)C26—C271.523 (6)
P4—O11.494 (3)C26—H26A0.9900
P4—C61.805 (4)C26—H26B0.9900
P4—C311.820 (5)C27—C281.514 (6)
P4—C371.837 (5)C27—H27A0.9900
Cl2—O63.170 (4)C27—H27B0.9900
Cl2—C53.654 (4)C28—C291.513 (5)
Cl2—C33.755 (4)C28—H28A0.9900
O1—O52.740 (4)C28—H28B0.9900
C1—C21.539 (5)C29—C301.527 (5)
C1—H1B0.9900C29—H29A0.9900
C1—H1C0.9900C29—H29B0.9900
C2—H2A0.9900C30—H30A0.9900
C2—H2B0.9900C30—H30B0.9900
C3—C41.537 (5)C31—C321.538 (6)
C3—H3A0.9900C31—C361.540 (6)
C3—H3B0.9900C31—H31A1.0000
C4—H4A0.9900C32—C331.520 (6)
C4—H4B0.9900C32—H32A0.9900
C5—C61.532 (5)C32—H32B0.9900
C5—H5A0.9900C33—C341.516 (6)
C5—H5B0.9900C33—H33A0.9900
C6—H6A0.9900C33—H33B0.9900
C6—H6B0.9900C34—C351.517 (6)
C7—C81.520 (6)C34—H34A0.9900
C7—C121.523 (6)C34—H34B0.9900
C7—H7A1.0000C35—C361.525 (6)
C8—C91.545 (5)C35—H35A0.9900
C8—H8A0.9900C35—H35B0.9900
C8—H8B0.9900C36—H36A0.9900
C9—C101.517 (6)C36—H36B0.9900
C9—H9A0.9900C37—C421.521 (6)
C9—H9B0.9900C37—C381.532 (6)
C10—C111.526 (6)C37—H37A1.0000
C10—H10A0.9900C38—C391.531 (6)
C10—H10B0.9900C38—H38A0.9900
C11—C121.516 (5)C38—H38B0.9900
C11—H11A0.9900C39—C401.503 (6)
C11—H11B0.9900C39—H39A0.9900
C12—H12A0.9900C39—H39B0.9900
C12—H12B0.9900C40—C411.520 (6)
C13—C181.534 (5)C40—H40A0.9900
C13—C141.535 (5)C40—H40B0.9900
C13—H13A1.0000C41—C421.520 (6)
C14—C151.530 (6)C41—H41A0.9900
C14—H14A0.9900C41—H41B0.9900
C14—H14B0.9900C42—H42A0.9900
C15—C161.515 (6)C42—H42B0.9900
C15—H15A0.9900O3—H3C0.8017
C15—H15B0.9900O3—H3D0.8847
C16—C171.536 (6)O4—H4D0.9154
C16—H16A0.9900O4—H4C0.7198
C16—H16B0.9900O5—O62.746 (5)
C17—C181.519 (6)O5—H5C0.7892
C17—H17A0.9900O5—H5D0.8623
C17—H17B0.9900O6—H6C0.80 (4)
C18—H18A0.9900O6—H6D0.81 (7)
C18—H18B0.9900Cl4—C991.750 (9)
C19—C201.535 (5)Cl5—C991.790 (10)
C19—C241.542 (6)Cl5—H98A1.51 (14)
C19—H19A1.0000C99—H99A0.9900
C20—C211.521 (5)C99—H99B0.9900
C20—H20A0.9900C98—H98Ai0.989 (10)
C20—H20B0.9900C98—Cl5Ai1.732 (19)
C21—C221.510 (6)C98—Cl5A1.732 (19)
C21—H21A0.9900C98—H98A0.989 (10)
P1—Pt1—P284.93 (4)C19—C20—H20B109.3
P1—Pt1—P386.57 (4)H20A—C20—H20B108.0
P2—Pt1—P3167.17 (4)C22—C21—C20111.7 (4)
P1—Pt1—Cl1176.99 (4)C22—C21—H21A109.3
P2—Pt1—Cl192.85 (4)C20—C21—H21A109.3
P3—Pt1—Cl195.26 (4)C22—C21—H21B109.3
C3—P1—C1112.32 (19)C20—C21—H21B109.3
C3—P1—C5106.1 (2)H21A—C21—H21B107.9
C1—P1—C5102.45 (19)C21—C22—C23110.7 (4)
C3—P1—Pt1109.77 (14)C21—C22—H22A109.5
C1—P1—Pt1106.73 (15)C23—C22—H22A109.5
C5—P1—Pt1119.40 (14)C21—C22—H22B109.5
C13—P2—C7105.74 (19)C23—C22—H22B109.5
C13—P2—C2107.4 (2)H22A—C22—H22B108.1
C7—P2—C2106.4 (2)C22—C23—C24110.7 (3)
C13—P2—Pt1111.21 (14)C22—C23—H23A109.5
C7—P2—Pt1119.04 (14)C24—C23—H23A109.5
C2—P2—Pt1106.54 (13)C22—C23—H23B109.5
C19—P3—C4105.7 (2)C24—C23—H23B109.5
C19—P3—C25106.02 (19)H23A—C23—H23B108.1
C4—P3—C25105.06 (19)C23—C24—C19110.5 (3)
C19—P3—Pt1118.86 (13)C23—C24—H24A109.6
C4—P3—Pt1106.41 (13)C19—C24—H24A109.6
C25—P3—Pt1113.66 (13)C23—C24—H24B109.6
O1—P4—C6111.06 (19)C19—C24—H24B109.6
O1—P4—C31111.98 (19)H24A—C24—H24B108.1
C6—P4—C31105.1 (2)C26—C25—C30110.0 (3)
O1—P4—C37110.13 (19)C26—C25—P3113.0 (3)
C6—P4—C37106.6 (2)C30—C25—P3112.0 (3)
C31—P4—C37111.8 (2)C26—C25—H25A107.1
O6—Cl2—C563.04 (12)C30—C25—H25A107.1
O6—Cl2—C3103.47 (14)P3—C25—H25A107.1
C5—Cl2—C346.01 (9)C27—C26—C25110.5 (4)
P4—O1—O5117.52 (17)C27—C26—H26A109.5
C2—C1—P1107.8 (3)C25—C26—H26A109.5
C2—C1—H1B110.1C27—C26—H26B109.5
P1—C1—H1B110.1C25—C26—H26B109.5
C2—C1—H1C110.1H26A—C26—H26B108.1
P1—C1—H1C110.1C28—C27—C26111.5 (4)
H1B—C1—H1C108.5C28—C27—H27A109.3
C1—C2—P2112.8 (3)C26—C27—H27A109.3
C1—C2—H2A109.0C28—C27—H27B109.3
P2—C2—H2A109.0C26—C27—H27B109.3
C1—C2—H2B109.0H27A—C27—H27B108.0
P2—C2—H2B109.0C29—C28—C27110.7 (4)
H2A—C2—H2B107.8C29—C28—H28A109.5
C4—C3—P1110.5 (3)C27—C28—H28A109.5
C4—C3—Cl2137.0 (3)C29—C28—H28B109.5
P1—C3—Cl288.84 (15)C27—C28—H28B109.5
C4—C3—H3A109.6H28A—C28—H28B108.1
P1—C3—H3A109.6C28—C29—C30111.2 (4)
C4—C3—H3B109.6C28—C29—H29A109.4
P1—C3—H3B109.6C30—C29—H29A109.4
Cl2—C3—H3B98.5C28—C29—H29B109.4
H3A—C3—H3B108.1C30—C29—H29B109.4
C3—C4—P3111.7 (3)H29A—C29—H29B108.0
C3—C4—H4A109.3C29—C30—C25111.9 (4)
P3—C4—H4A109.3C29—C30—H30A109.2
C3—C4—H4B109.3C25—C30—H30A109.2
P3—C4—H4B109.3C29—C30—H30B109.2
H4A—C4—H4B107.9C25—C30—H30B109.2
C6—C5—P1115.5 (3)H30A—C30—H30B107.9
C6—C5—Cl2118.8 (3)C32—C31—C36110.3 (4)
P1—C5—Cl291.79 (15)C32—C31—P4110.7 (3)
C6—C5—H5A108.4C36—C31—P4110.1 (3)
P1—C5—H5A108.4C32—C31—H31A108.5
Cl2—C5—H5A112.9C36—C31—H31A108.5
C6—C5—H5B108.4P4—C31—H31A108.5
P1—C5—H5B108.4C33—C32—C31112.9 (4)
H5A—C5—H5B107.5C33—C32—H32A109.0
C5—C6—P4111.8 (3)C31—C32—H32A109.0
C5—C6—H6A109.3C33—C32—H32B109.0
P4—C6—H6A109.3C31—C32—H32B109.0
C5—C6—H6B109.3H32A—C32—H32B107.8
P4—C6—H6B109.3C34—C33—C32113.6 (4)
H6A—C6—H6B107.9C34—C33—H33A108.8
C8—C7—C12110.7 (4)C32—C33—H33A108.8
C8—C7—P2112.7 (3)C34—C33—H33B108.8
C12—C7—P2111.3 (3)C32—C33—H33B108.8
C8—C7—H7A107.3H33A—C33—H33B107.7
C12—C7—H7A107.3C33—C34—C35110.2 (4)
P2—C7—H7A107.3C33—C34—H34A109.6
C7—C8—C9110.7 (4)C35—C34—H34A109.6
C7—C8—H8A109.5C33—C34—H34B109.6
C9—C8—H8A109.5C35—C34—H34B109.6
C7—C8—H8B109.5H34A—C34—H34B108.1
C9—C8—H8B109.5C34—C35—C36110.8 (4)
H8A—C8—H8B108.1C34—C35—H35A109.5
C10—C9—C8111.7 (4)C36—C35—H35A109.5
C10—C9—H9A109.3C34—C35—H35B109.5
C8—C9—H9A109.3C36—C35—H35B109.5
C10—C9—H9B109.3H35A—C35—H35B108.1
C8—C9—H9B109.3C35—C36—C31113.1 (4)
H9A—C9—H9B107.9C35—C36—H36A109.0
C9—C10—C11111.6 (4)C31—C36—H36A109.0
C9—C10—H10A109.3C35—C36—H36B109.0
C11—C10—H10A109.3C31—C36—H36B109.0
C9—C10—H10B109.3H36A—C36—H36B107.8
C11—C10—H10B109.3C42—C37—C38110.6 (4)
H10A—C10—H10B108.0C42—C37—P4113.8 (3)
C12—C11—C10111.1 (4)C38—C37—P4115.6 (3)
C12—C11—H11A109.4C42—C37—H37A105.2
C10—C11—H11A109.4C38—C37—H37A105.2
C12—C11—H11B109.4P4—C37—H37A105.2
C10—C11—H11B109.4C39—C38—C37110.2 (4)
H11A—C11—H11B108.0C39—C38—H38A109.6
C11—C12—C7112.4 (4)C37—C38—H38A109.6
C11—C12—H12A109.1C39—C38—H38B109.6
C7—C12—H12A109.1C37—C38—H38B109.6
C11—C12—H12B109.1H38A—C38—H38B108.1
C7—C12—H12B109.1C40—C39—C38110.9 (4)
H12A—C12—H12B107.9C40—C39—H39A109.5
C18—C13—C14110.6 (4)C38—C39—H39A109.5
C18—C13—P2112.9 (3)C40—C39—H39B109.5
C14—C13—P2114.1 (3)C38—C39—H39B109.5
C18—C13—H13A106.2H39A—C39—H39B108.1
C14—C13—H13A106.2C39—C40—C41110.3 (4)
P2—C13—H13A106.2C39—C40—H40A109.6
C15—C14—C13111.7 (4)C41—C40—H40A109.6
C15—C14—H14A109.3C39—C40—H40B109.6
C13—C14—H14A109.3C41—C40—H40B109.6
C15—C14—H14B109.3H40A—C40—H40B108.1
C13—C14—H14B109.3C40—C41—C42111.1 (4)
H14A—C14—H14B108.0C40—C41—H41A109.4
C16—C15—C14111.3 (4)C42—C41—H41A109.4
C16—C15—H15A109.4C40—C41—H41B109.4
C14—C15—H15A109.4C42—C41—H41B109.4
C16—C15—H15B109.4H41A—C41—H41B108.0
C14—C15—H15B109.4C41—C42—C37111.6 (4)
H15A—C15—H15B108.0C41—C42—H42A109.3
C15—C16—C17110.0 (4)C37—C42—H42A109.3
C15—C16—H16A109.7C41—C42—H42B109.3
C17—C16—H16A109.7C37—C42—H42B109.3
C15—C16—H16B109.7H42A—C42—H42B108.0
C17—C16—H16B109.7H3C—O3—H3D102.7
H16A—C16—H16B108.2H4D—O4—H4C112.1
C18—C17—C16111.3 (4)O1—O5—O6114.12 (14)
C18—C17—H17A109.4O6—O5—H5C113.4
C16—C17—H17A109.4O1—O5—H5D105.0
C18—C17—H17B109.4H5C—O5—H5D104.2
C16—C17—H17B109.4O5—O6—Cl2131.45 (17)
H17A—C17—H17B108.0O5—O6—H6C136 (6)
C17—C18—C13110.1 (4)O5—O6—H6D118 (6)
C17—C18—H18A109.6Cl2—O6—H6D106 (6)
C13—C18—H18A109.6H6C—O6—H6D106 (7)
C17—C18—H18B109.6C99—Cl5—H98A103 (5)
C13—C18—H18B109.6Cl4—C99—Cl5112.0 (8)
H18A—C18—H18B108.2Cl4—C99—H99A109.2
C20—C19—C24109.2 (3)Cl5—C99—H99A109.2
C20—C19—P3111.0 (3)Cl4—C99—H99B109.2
C24—C19—P3113.8 (3)Cl5—C99—H99B109.2
C20—C19—H19A107.5H99A—C99—H99B107.9
C24—C19—H19A107.5H98Ai—C98—Cl5Ai97 (10)
P3—C19—H19A107.5H98Ai—C98—Cl5A124 (9)
C21—C20—C19111.6 (3)Cl5Ai—C98—Cl5A109.2 (18)
C21—C20—H20A109.3H98Ai—C98—H98A107 (10)
C19—C20—H20A109.3Cl5Ai—C98—H98A124 (9)
C21—C20—H20B109.3Cl5A—C98—H98A97 (10)

Symmetry codes: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3C···Cl2ii0.802.503.300 (3)175
O3—H3D···Cl20.882.433.290 (4)166
O4—H4C···O30.732.162.866 (4)165
O4—H4D···O5iii0.921.822.730 (4)174
O5—H5C···O10.801.942.740 (4)179
O5—H5D···O60.871.922.746 (5)159
O6—H6C···Cl20.80 (4)2.43 (4)3.170 (4)155 (8)
O6—H6D···Cl2iii0.81 (7)2.40 (7)3.200 (4)175 (9)
C3—H3A···Cl20.992.923.755 (4)142
C5—H5B···Cl20.992.723.655 (4)157

Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) −x+1, y, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2731).

References

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  • Brüggeller, P., Nar, H. & Messerschmidt, A. (1992). Acta Cryst. C48, 817–821.
  • Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Poverenov, E., Efremenko, I., Frenkel, A. I., Ben-David, Y., Shimon, L. J. W., Leitus, G., Konstantinovski, L., Martin, J. M. L. & Milstein, D. (2008). Nature (London), 455, 1093–1096.
  • Rieckborn, T. P., Karakoc, E. & Prosenc, M. H. (2008). Acta Cryst. E64, m898–m899. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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