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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1707.
Published online 2009 November 28. doi:  10.1107/S1600536809050910
PMCID: PMC2971967

Chloridocyclo­hexyl[(1,2,5,6-η)-cyclo­octa-1,5-diene]platinum(II)

Abstract

In the title complex, [Pt(C6H11)Cl(C8H12)], the PtII ion lies in a distorted square-planar environment defined by the Cl and cyclo­hexyl C atoms and the mid-points of the two π-coordinated double bonds of cyclo­octa-1,5-diene. As a result of the different trans influences of the Cl atom and the cyclo­hexyl group, the Pt—C bonds trans to the cyclo­hexyl group are longer than those trans to the Cl atom.

Related literature

For the crystal structure of [(cod)PtCl2] (cod = cyclo­octa-1,5-diene), see: Goel et al. (1982 [triangle]); Syed et al. (1984 [triangle]). For the crystal structures of [(cod)Pt(CH3)L] (L = OH, CH3 or Cl), see: Klein et al. (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1707-scheme1.jpg

Experimental

Crystal data

  • [Pt(C6H11)Cl(C8H12)]
  • M r = 421.86
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1707-efi1.jpg
  • a = 10.6505 (5) Å
  • b = 12.3514 (6) Å
  • c = 11.1609 (6) Å
  • β = 105.175 (1)°
  • V = 1417.01 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 10.06 mm−1
  • T = 296 K
  • 0.20 × 0.16 × 0.15 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.122, T max = 0.221
  • 10108 measured reflections
  • 3481 independent reflections
  • 2343 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.083
  • S = 1.12
  • 3481 reflections
  • 145 parameters
  • H-atom parameters constrained
  • Δρmax = 1.12 e Å−3
  • Δρmin = −1.79 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: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050910/ng2696sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050910/ng2696Isup2.hkl

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

Acknowledgments

This work was supported by a Korea Research Foundation grant funded by the Korean Government (MOEHRD) (KRF-2007–412-J02001).

supplementary crystallographic information

Comment

In the title complex, [Pt(C6H11)Cl(C8H12)], the central PtII ion lies in a distorted square-planar environment defined by the Cl and cyclohexyl C atoms and the two mid-points (M1, M2) of the π-coordinated double bonds of cycloocta-1,5-diene (cod) ligand (M1 and M2 denote the mid-points of the olefinic bonds C1—C2 and C5—C6, respectively) (Fig. 1 and Fig. 2). The Pt, Cl, C9 atoms and the mid-points lie in a coordination plane with the largest deviation of 0.021 Å (C9) from the least-squares plane, and with bond angles in the range of 85.2°–92.2°. Because of the different trans influences of the Cl atom and the cyclohexyl group, the Pt—C bonds trans to C9 of the cyclohexyl group are on average 0.215 Å longer than those trans to the Cl atom (Pt1—C1/C2 = 2.316 (7) and 2.337 (8) Å, Pt1—C5/C6 = 2.111 (8) and 2.112 (8) Å). The distances between the Pt atom and the mid-points are 2.228 Å (M1) and 1.992 Å (M2). The cod ligand coordinates to the Pt atom in the twist-boat conformation with the coordinated double-bond lengths of 1.339 (11) and 1.402 (12) Å, and the cod ring angles lie in the range of 113.0 (8)°–127.1 (8)°. The σ-bonded cyclohexyl ring is in the chair conformation with the ring angles of 109.9 (8)°–112.0 (8)°.

Experimental

To a suspension of [(cod)PtCl2] (0.5015 g, 1.34 mmol) in ether (30 ml) was added cyclohexylmagnesium chloride (2.0 M solution in ether, 4.1 ml, 8.04 mmol) and stirred for 24 h at -5 °C. After methanolysis with 1 ml MeOH, the resulting mixture was diluted with ether (20 ml), and then filtered directly through a plug of Al2O3 (3 cm x 2 cm) and eluted with ether (80 ml). The solvent was removed under vacuum and the residue was dried, to give a white powder (0.3655 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from an ethyl acetate solution.

Refinement

H atoms were positioned geometrically and allowed to ride on their respective parent atoms [C—H = 0.98 (CH) or 0.97 (CH2) Å and Uiso(H) = 1.2Ueq(C)].

Figures

Fig. 1.
The structure of the title compound, with displacement ellipsoids drawn at the 30% probability level for non-H atoms.
Fig. 2.
View of the unit-cell contents of the title compound.

Crystal data

[Pt(C6H11)Cl(C8H12)]F(000) = 808
Mr = 421.86Dx = 1.977 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3669 reflections
a = 10.6505 (5) Åθ = 2.4–27.8°
b = 12.3514 (6) ŵ = 10.06 mm1
c = 11.1609 (6) ÅT = 296 K
β = 105.175 (1)°Block, colorless
V = 1417.01 (12) Å30.20 × 0.16 × 0.15 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer3481 independent reflections
Radiation source: fine-focus sealed tube2343 reflections with I > 2σ(I)
graphiteRint = 0.050
[var phi] and ω scansθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −14→14
Tmin = 0.122, Tmax = 0.221k = −8→16
10108 measured reflectionsl = −14→14

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.12w = 1/[σ2(Fo2) + (0.0112P)2 + 4.7457P] where P = (Fo2 + 2Fc2)/3
3481 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 1.12 e Å3
0 restraintsΔρmin = −1.79 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*/Ueq
Pt10.23435 (3)0.38659 (3)0.59178 (3)0.03388 (11)
Cl10.0531 (2)0.2747 (2)0.5501 (2)0.0491 (6)
C10.1992 (9)0.4337 (7)0.7812 (7)0.043 (2)
H10.13720.38700.80780.051*
C20.1440 (8)0.5121 (8)0.7019 (8)0.044 (2)
H20.04870.51320.68010.052*
C30.2067 (9)0.6204 (8)0.6984 (8)0.053 (2)
H3A0.26250.63640.78020.064*
H3B0.13960.67550.67850.064*
C40.2864 (10)0.6255 (8)0.6048 (9)0.063 (3)
H4A0.22990.64770.52560.076*
H4B0.35220.68120.63080.076*
C50.3523 (8)0.5229 (7)0.5861 (8)0.043 (2)
H50.38650.52430.51280.052*
C60.4195 (8)0.4513 (8)0.6782 (9)0.052 (3)
H60.49210.41350.65780.062*
C70.4382 (10)0.4719 (9)0.8158 (9)0.068 (3)
H7A0.51690.43510.86070.082*
H7B0.45220.54890.83070.082*
C80.3306 (11)0.4376 (9)0.8696 (8)0.065 (3)
H8A0.32760.48700.93640.078*
H8B0.35100.36630.90580.078*
C90.3060 (8)0.3085 (8)0.4561 (8)0.044 (2)
H90.38820.34380.45540.053*
C100.2166 (11)0.3210 (9)0.3290 (8)0.064 (3)
H10A0.20230.39740.30990.076*
H10B0.13320.28830.32670.076*
C110.2741 (13)0.2672 (11)0.2310 (10)0.087 (4)
H11A0.21160.27180.15040.105*
H11B0.35170.30600.22620.105*
C120.3075 (11)0.1516 (9)0.2608 (10)0.071 (3)
H12A0.35130.12270.20170.085*
H12B0.22820.11050.25300.085*
C130.3945 (10)0.1387 (9)0.3909 (9)0.067 (3)
H13A0.47850.17130.39520.080*
H13B0.40830.06220.40960.080*
C140.3359 (9)0.1916 (8)0.4883 (8)0.051 (2)
H14A0.25670.15400.49110.061*
H14B0.39680.18630.56960.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pt10.03384 (17)0.03547 (19)0.03338 (16)−0.00364 (17)0.01065 (11)−0.00381 (18)
Cl10.0403 (12)0.0527 (15)0.0538 (13)−0.0132 (10)0.0116 (10)−0.0063 (12)
C10.070 (6)0.037 (5)0.028 (4)0.006 (5)0.025 (4)−0.004 (4)
C20.042 (5)0.048 (6)0.043 (5)0.007 (4)0.015 (4)−0.006 (5)
C30.056 (6)0.054 (7)0.048 (5)0.012 (5)0.010 (4)0.002 (5)
C40.075 (7)0.046 (7)0.072 (7)−0.006 (5)0.026 (6)−0.009 (6)
C50.049 (5)0.044 (6)0.049 (5)−0.020 (4)0.031 (4)−0.019 (5)
C60.030 (5)0.053 (6)0.068 (6)−0.015 (4)0.005 (4)−0.018 (6)
C70.062 (7)0.067 (8)0.058 (6)0.000 (6)−0.014 (5)−0.007 (6)
C80.096 (9)0.055 (7)0.035 (5)0.017 (6)0.000 (5)−0.006 (5)
C90.049 (5)0.047 (6)0.042 (5)−0.008 (4)0.022 (4)−0.018 (4)
C100.096 (8)0.056 (7)0.046 (6)0.018 (6)0.033 (6)0.007 (5)
C110.121 (11)0.108 (12)0.047 (6)0.015 (9)0.046 (7)−0.009 (7)
C120.084 (8)0.061 (8)0.080 (8)0.000 (6)0.042 (7)−0.024 (7)
C130.072 (7)0.064 (8)0.072 (7)0.010 (6)0.032 (6)−0.012 (6)
C140.056 (6)0.045 (6)0.057 (6)0.008 (5)0.026 (5)−0.013 (5)

Geometric parameters (Å, °)

Pt1—C92.100 (8)C7—H7A0.9700
Pt1—C52.111 (8)C7—H7B0.9700
Pt1—C62.112 (8)C8—H8A0.9700
Pt1—C12.316 (7)C8—H8B0.9700
Pt1—Cl12.320 (2)C9—C101.495 (12)
Pt1—C22.337 (8)C9—C141.502 (12)
C1—C21.339 (11)C9—H90.9800
C1—C81.487 (13)C10—C111.538 (12)
C1—H10.9800C10—H10A0.9700
C2—C31.500 (13)C10—H10B0.9700
C2—H20.9800C11—C121.488 (15)
C3—C41.510 (12)C11—H11A0.9700
C3—H3A0.9700C11—H11B0.9700
C3—H3B0.9700C12—C131.513 (14)
C4—C51.490 (13)C12—H12A0.9700
C4—H4A0.9700C12—H12B0.9700
C4—H4B0.9700C13—C141.534 (11)
C5—C61.402 (12)C13—H13A0.9700
C5—H50.9800C13—H13B0.9700
C6—C71.517 (12)C14—H14A0.9700
C6—H60.9800C14—H14B0.9700
C7—C81.487 (14)
C9—Pt1—C590.8 (3)Pt1—C6—H6114.4
C9—Pt1—C691.8 (4)C8—C7—C6116.8 (8)
C5—Pt1—C638.8 (3)C8—C7—H7A108.1
C9—Pt1—C1161.8 (3)C6—C7—H7A108.1
C5—Pt1—C193.8 (3)C8—C7—H7B108.1
C6—Pt1—C180.9 (4)C6—C7—H7B108.1
C9—Pt1—Cl191.3 (2)H7A—C7—H7B107.3
C5—Pt1—Cl1159.9 (3)C7—C8—C1115.6 (8)
C6—Pt1—Cl1160.9 (3)C7—C8—H8A108.4
C1—Pt1—Cl190.5 (2)C1—C8—H8A108.4
C9—Pt1—C2164.0 (3)C7—C8—H8B108.4
C5—Pt1—C279.5 (3)C1—C8—H8B108.4
C6—Pt1—C288.4 (4)H8A—C8—H8B107.4
C1—Pt1—C233.5 (3)C10—C9—C14111.7 (8)
Cl1—Pt1—C293.7 (2)C10—C9—Pt1112.0 (6)
C2—C1—C8126.1 (9)C14—C9—Pt1111.3 (6)
C2—C1—Pt174.1 (5)C10—C9—H9107.2
C8—C1—Pt1105.4 (6)C14—C9—H9107.2
C2—C1—H1114.3Pt1—C9—H9107.2
C8—C1—H1114.3C9—C10—C11110.9 (9)
Pt1—C1—H1114.3C9—C10—H10A109.5
C1—C2—C3122.7 (8)C11—C10—H10A109.5
C1—C2—Pt172.4 (5)C9—C10—H10B109.5
C3—C2—Pt1109.3 (6)C11—C10—H10B109.5
C1—C2—H2114.9H10A—C10—H10B108.0
C3—C2—H2114.9C12—C11—C10111.9 (9)
Pt1—C2—H2114.9C12—C11—H11A109.2
C2—C3—C4113.0 (8)C10—C11—H11A109.2
C2—C3—H3A109.0C12—C11—H11B109.2
C4—C3—H3A109.0C10—C11—H11B109.2
C2—C3—H3B109.0H11A—C11—H11B107.9
C4—C3—H3B109.0C11—C12—C13111.5 (10)
H3A—C3—H3B107.8C11—C12—H12A109.3
C5—C4—C3115.5 (9)C13—C12—H12A109.3
C5—C4—H4A108.4C11—C12—H12B109.3
C3—C4—H4A108.4C13—C12—H12B109.3
C5—C4—H4B108.4H12A—C12—H12B108.0
C3—C4—H4B108.4C12—C13—C14112.0 (8)
H4A—C4—H4B107.5C12—C13—H13A109.2
C6—C5—C4127.1 (8)C14—C13—H13A109.2
C6—C5—Pt170.7 (5)C12—C13—H13B109.2
C4—C5—Pt1111.6 (6)C14—C13—H13B109.2
C6—C5—H5113.2H13A—C13—H13B107.9
C4—C5—H5113.2C9—C14—C13109.9 (8)
Pt1—C5—H5113.2C9—C14—H14A109.7
C5—C6—C7122.9 (9)C13—C14—H14A109.7
C5—C6—Pt170.6 (5)C9—C14—H14B109.7
C7—C6—Pt1112.7 (6)C13—C14—H14B109.7
C5—C6—H6114.4H14A—C14—H14B108.2
C7—C6—H6114.4
C9—Pt1—C1—C2168.5 (9)C9—Pt1—C6—C589.0 (6)
C5—Pt1—C1—C264.3 (6)C1—Pt1—C6—C5−107.8 (5)
C6—Pt1—C1—C2101.0 (6)Cl1—Pt1—C6—C5−171.9 (6)
Cl1—Pt1—C1—C2−96.1 (6)C2—Pt1—C6—C5−75.0 (5)
C9—Pt1—C1—C844.6 (14)C9—Pt1—C6—C7−152.5 (8)
C5—Pt1—C1—C8−59.5 (7)C5—Pt1—C6—C7118.5 (10)
C6—Pt1—C1—C8−22.8 (7)C1—Pt1—C6—C710.6 (7)
Cl1—Pt1—C1—C8140.1 (6)Cl1—Pt1—C6—C7−53.4 (13)
C2—Pt1—C1—C8−123.8 (9)C2—Pt1—C6—C743.4 (8)
C8—C1—C2—C3−4.3 (14)C5—C6—C7—C884.8 (12)
Pt1—C1—C2—C3−102.0 (8)Pt1—C6—C7—C84.0 (12)
C8—C1—C2—Pt197.7 (9)C6—C7—C8—C1−26.2 (14)
C9—Pt1—C2—C1−166.9 (10)C2—C1—C8—C7−49.3 (13)
C5—Pt1—C2—C1−113.8 (6)Pt1—C1—C8—C732.0 (10)
C6—Pt1—C2—C1−75.9 (6)C5—Pt1—C9—C10−97.5 (7)
Cl1—Pt1—C2—C185.2 (6)C6—Pt1—C9—C10−136.2 (7)
C9—Pt1—C2—C3−47.6 (15)C1—Pt1—C9—C10157.9 (9)
C5—Pt1—C2—C35.4 (6)Cl1—Pt1—C9—C1062.6 (7)
C6—Pt1—C2—C343.4 (6)C2—Pt1—C9—C10−45.7 (15)
C1—Pt1—C2—C3119.3 (9)C5—Pt1—C9—C14136.7 (7)
Cl1—Pt1—C2—C3−155.5 (6)C6—Pt1—C9—C1498.0 (7)
C1—C2—C3—C493.5 (10)C1—Pt1—C9—C1432.1 (14)
Pt1—C2—C3—C412.5 (9)Cl1—Pt1—C9—C14−63.2 (6)
C2—C3—C4—C5−33.3 (12)C2—Pt1—C9—C14−171.5 (10)
C3—C4—C5—C6−43.5 (13)C14—C9—C10—C11−56.8 (11)
C3—C4—C5—Pt138.1 (10)Pt1—C9—C10—C11177.6 (7)
C9—Pt1—C5—C6−91.9 (6)C9—C10—C11—C1254.8 (14)
C1—Pt1—C5—C670.4 (6)C10—C11—C12—C13−53.3 (14)
Cl1—Pt1—C5—C6172.3 (6)C11—C12—C13—C1454.1 (13)
C2—Pt1—C5—C6100.8 (6)C10—C9—C14—C1356.9 (10)
C9—Pt1—C5—C4144.8 (7)Pt1—C9—C14—C13−177.1 (6)
C6—Pt1—C5—C4−123.2 (9)C12—C13—C14—C9−55.3 (12)
C1—Pt1—C5—C4−52.8 (7)C1—C2—C5—C6−7.2 (7)
Cl1—Pt1—C5—C449.1 (11)C3—C4—C7—C822.4 (8)
C2—Pt1—C5—C4−22.5 (7)C3—C2—C1—C8−4.3 (14)
C4—C5—C6—C7−2.0 (14)C4—C5—C6—C7−2.0 (14)
Pt1—C5—C6—C7−105.0 (9)C2—C3—C4—C5−33.3 (12)
C4—C5—C6—Pt1103.0 (9)C6—C7—C8—C1−26.2 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2696).

References

  • Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
  • Goel, A. B., Goel, S. & van der Veer, D. (1982). Inorg. Chim. Acta, 65, L205–L206.
  • Klein, A., Klinkhammer, K.-W. & Scheiring, T. (1999). J. Organomet. Chem. 592, 128–135.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Syed, A., Stevens, E. D. & Cruz, S. G. (1984). Inorg. Chem. 23, 3673–3674.

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