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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): m927.
Published online 2008 June 19. doi:  10.1107/S1600536808017194
PMCID: PMC2961756

1,1′-Bis(diisobutyl­phosphino)cobalto­cenium hexa­fluorido­phosphate

Abstract

In the title compound, [Co(C13H22P)2]PF6, the CoIII atom is sandwiched between two (diisobutyl­phosphino)cyclo­penta­dienenyl ligands. The two diisobutyl­phophine units are trans to each other with respect to the CoIII metal center. The PF6 anion links the cobaltocenium cations via weak C—H(...)F hydrogen bonds into a chain running along the b axis. The chains are further linked by C—H(...)F hydrogen bonds, forming a layer extending parallel to the (10An external file that holds a picture, illustration, etc.
Object name is e-64-0m927-efi1.jpg) plane.

Related literature

For background to cobaltocene derivatives applied as catal­ysts, see: Mathews et al. (2000 [triangle]). For the structures of closely related compounds, see: Brasse et al. (2000 [triangle]); Hou et al. (2007 [triangle]).

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Object name is e-64-0m927-scheme1.jpg

Experimental

Crystal data

  • [Co(C13H22P)2]·PF6
  • M r = 622.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m927-efi2.jpg
  • a = 16.7733 (3) Å
  • b = 10.4660 (2) Å
  • c = 18.5105 (4) Å
  • β = 108.288 (1)°
  • V = 3085.38 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.76 mm−1
  • T = 298 (2) K
  • 0.40 × 0.04 × 0.02 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.750, T max = 0.985
  • 33818 measured reflections
  • 6733 independent reflections
  • 3878 reflections with I > 2σ(I)
  • R int = 0.083

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.147
  • S = 0.97
  • 6733 reflections
  • 333 parameters
  • H-atom parameters constrained
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017194/is2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017194/is2295Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20572029), New Century Excellent Talents in Universities (NCET-04–0743), the Cultivation Fund of the Key Scientific and Technical Innovation Project, Ministry of Education of China (grant No. 705039).

supplementary crystallographic information

Comment

Cobaltocene derivatives have been applied as catalysts in cross-coupling reactions (Mathews et al., 2000). As part of our investigations of new catalysts, we have focused our attention on cobaltocenium compounds. Some complexes, such as 1,1'-bis(diphenylphosphino)cobaltocenium tetrafluoridoborate, have been obtained and reported (Hou et al., 2007). Herein, we report the structure of the title compound, (I) (Fig. 1). The molecular structure of the title complex consists of the [(η5-(i-C4H9)2PC5H4)2Co]+ cation and the PF6- anion, which is very similar to the compounds 1,1'-bis(diphenylphosphino)cobaltocenium tetrafluoridoborate (Hou et al., 2007) and 1,1'-bis(diphenylphosphino)cobaltocenium hexafluorophosphate with different substituents (Brasse et al., 2000). The two (i-C4H9)2P substituents are trans to each other with respect to the CoIII metal center, and the two substituted Cp rings staggered and are essentially parallel with a dihedral angle of 1.8 (2)°. The Co1···Cg1 and Co1···Cg2 distances are 1.6429 (15) and 1.6430 (3) Å, respectively, and the Cg1···Co1···Cg2 angle is 179.13 (8)° (Cg1 and Cg2 are the centroids of the two cyclopentadienyl) The hydrogen bonds of C—H···F play a key role of the stabilization of crystal structure of the title compound. As shown in Fig. 2, there are extensive nonclassical hydrogen bonds formed by C—H···F (Table 2). There are not only intramolecular but also intermolecular hydrogen bonds between the cation and anion, thus, two-dimensional layers extending parallel to the (101) plane were formed.

Experimental

The title compound was obtained by anion exchange of 1,1'-bis(di-isobutylphosphino)cobaltocenium chloride with ammonium hexaflurophosphate. Crystals appropriate for data collection were obtained by slow diffusion of hexane into a solution of the title compound in dichloromethane at 293 K.

Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.96–0.98 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I), showing ellipsoids at 30% probability level.
Fig. 2.
The packing diagram of two-dimensional sheet with hydrogen bonds shown as dashed lines. H atoms not involved in the hydrogen bonds have been omitted for clarity.

Crystal data

[Co(C13H22P)2]·PF6F000 = 1304
Mr = 622.45Dx = 1.340 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3150 reflections
a = 16.7733 (3) Åθ = 2.3–19.9º
b = 10.4660 (2) ŵ = 0.76 mm1
c = 18.5105 (4) ÅT = 298 (2) K
β = 108.288 (1)ºNeedle, yellow
V = 3085.38 (10) Å30.40 × 0.04 × 0.02 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer6733 independent reflections
Radiation source: fine-focus sealed tube3878 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.083
T = 298(2) Kθmax = 27.0º
[var phi] and ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)h = −21→21
Tmin = 0.750, Tmax = 0.985k = −13→13
33818 measured reflectionsl = −23→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.147  w = 1/[σ2(Fo2) + (0.0731P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
6733 reflectionsΔρmax = 0.47 e Å3
333 parametersΔρmin = −0.34 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
Co10.66580 (3)0.34637 (4)0.07609 (2)0.04054 (16)
C10.6975 (2)0.3487 (3)−0.02171 (18)0.0413 (8)
C20.6752 (2)0.2221 (3)−0.00492 (18)0.0480 (9)
H20.71190.14700.00380.058*
C30.5916 (2)0.2239 (4)−0.0027 (2)0.0560 (10)
H30.56080.15070.00810.067*
C40.5606 (2)0.3499 (4)−0.01797 (19)0.0542 (10)
H40.50470.3794−0.01930.065*
C50.6254 (2)0.4270 (3)−0.02941 (18)0.0468 (9)
H50.62150.5189−0.04020.056*
C60.7928 (2)0.5658 (3)−0.0360 (2)0.0558 (10)
H6A0.75260.5870−0.08490.067*
H6B0.77170.59930.00330.067*
C70.8757 (3)0.6294 (4)−0.0295 (3)0.0740 (13)
H70.89980.5880−0.06550.089*
C80.9371 (3)0.6159 (6)0.0495 (3)0.126 (2)
H8A0.91620.66080.08500.189*
H8B0.99040.65110.05070.189*
H8C0.94390.52710.06300.189*
C90.8631 (3)0.7712 (4)−0.0501 (3)0.1105 (19)
H9A0.83790.8127−0.01640.166*
H9B0.82700.7798−0.10160.166*
H9C0.91640.8099−0.04510.166*
C100.7851 (2)0.3465 (4)−0.1272 (2)0.0562 (10)
H10A0.73440.3882−0.15860.067*
H10B0.83160.3803−0.14190.067*
C110.7776 (3)0.2041 (4)−0.1449 (2)0.0694 (12)
H110.73000.1710−0.13060.083*
C120.7589 (3)0.1826 (5)−0.2301 (3)0.1059 (18)
H12A0.80420.2160−0.24580.159*
H12B0.70770.2256−0.25730.159*
H12C0.75300.0928−0.24090.159*
C130.8552 (4)0.1312 (4)−0.1000 (3)0.1079 (19)
H13A0.85060.0440−0.11700.162*
H13B0.86030.1337−0.04690.162*
H13C0.90390.1695−0.10770.162*
C140.6338 (2)0.3542 (3)0.17449 (18)0.0406 (8)
C150.7006 (2)0.2654 (3)0.18142 (18)0.0470 (9)
H150.69890.17390.19210.056*
C160.7687 (2)0.3305 (4)0.16930 (19)0.0576 (10)
H160.82240.29230.17060.069*
C170.7466 (2)0.4595 (4)0.15524 (19)0.0574 (10)
H170.78210.52690.14500.069*
C180.6640 (2)0.4751 (3)0.15777 (18)0.0493 (9)
H180.63230.55540.14920.059*
C190.5497 (2)0.3896 (3)0.28119 (19)0.0528 (9)
H19A0.50860.35200.30180.063*
H19B0.60460.35980.31200.063*
C200.5469 (3)0.5333 (4)0.2898 (2)0.0699 (12)
H200.58770.57080.26800.084*
C210.4615 (4)0.5887 (5)0.2477 (3)0.114 (2)
H21A0.42080.55780.27020.171*
H21B0.44550.56320.19530.171*
H21C0.46400.68030.25100.171*
C220.5730 (3)0.5705 (5)0.3741 (2)0.0917 (15)
H22A0.57170.66180.37860.138*
H22B0.62880.54010.39930.138*
H22C0.53480.53290.39730.138*
C230.5366 (2)0.1557 (3)0.2033 (2)0.0605 (10)
H23A0.54770.11200.16120.073*
H23B0.58420.14050.24840.073*
C240.4590 (3)0.0970 (4)0.2154 (3)0.0708 (12)
H240.44820.14310.25750.085*
C250.3822 (3)0.1080 (5)0.1483 (3)0.115 (2)
H25A0.39070.06320.10600.172*
H25B0.37110.19640.13520.172*
H25C0.33540.07140.16020.172*
C260.4769 (3)−0.0421 (4)0.2402 (4)0.113 (2)
H26A0.4304−0.07610.25380.169*
H26B0.5269−0.04640.28320.169*
H26C0.4846−0.09100.19900.169*
F10.63466 (15)0.7385 (2)0.03501 (14)0.0871 (8)
F20.75008 (15)0.7617 (2)0.13489 (16)0.0953 (9)
F30.71730 (17)0.9112 (3)0.04222 (16)0.0973 (8)
F40.70793 (18)0.9559 (2)0.15705 (15)0.1059 (10)
F50.59126 (16)0.9334 (2)0.05722 (17)0.1051 (9)
F60.62383 (18)0.7849 (3)0.14848 (15)0.0981 (8)
P10.80124 (6)0.39039 (9)−0.02673 (5)0.0469 (3)
P20.52962 (6)0.32919 (9)0.18315 (5)0.0476 (3)
P30.67083 (6)0.84835 (9)0.09545 (6)0.0561 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0484 (3)0.0352 (3)0.0388 (3)−0.0031 (2)0.0149 (2)−0.0013 (2)
C10.0513 (19)0.0361 (19)0.0372 (17)−0.0008 (16)0.0150 (15)−0.0037 (15)
C20.069 (2)0.033 (2)0.044 (2)−0.0023 (17)0.0203 (17)−0.0092 (16)
C30.066 (2)0.052 (3)0.052 (2)−0.0226 (19)0.0213 (19)−0.0142 (19)
C40.048 (2)0.063 (3)0.045 (2)−0.0019 (19)0.0064 (16)−0.0064 (19)
C50.053 (2)0.044 (2)0.0401 (19)0.0021 (17)0.0109 (16)0.0053 (16)
C60.061 (2)0.043 (2)0.067 (2)−0.0035 (18)0.0257 (19)0.0008 (18)
C70.078 (3)0.057 (3)0.094 (3)−0.019 (2)0.036 (3)−0.011 (2)
C80.089 (4)0.107 (4)0.150 (5)−0.031 (3)−0.008 (4)−0.014 (4)
C90.123 (4)0.060 (3)0.148 (5)−0.031 (3)0.041 (4)0.010 (3)
C100.066 (2)0.062 (3)0.047 (2)−0.0002 (19)0.0268 (18)0.0003 (19)
C110.083 (3)0.068 (3)0.072 (3)−0.021 (2)0.046 (2)−0.022 (2)
C120.129 (4)0.121 (5)0.081 (4)−0.029 (4)0.051 (3)−0.042 (3)
C130.163 (5)0.062 (3)0.101 (4)0.027 (3)0.046 (4)−0.014 (3)
C140.055 (2)0.0317 (19)0.0366 (18)0.0033 (15)0.0173 (15)−0.0004 (15)
C150.060 (2)0.043 (2)0.0408 (19)0.0072 (17)0.0193 (17)0.0054 (16)
C160.051 (2)0.076 (3)0.043 (2)0.005 (2)0.0113 (17)0.001 (2)
C170.067 (3)0.065 (3)0.041 (2)−0.022 (2)0.0178 (18)−0.0124 (19)
C180.074 (3)0.034 (2)0.041 (2)−0.0064 (17)0.0211 (18)−0.0087 (16)
C190.063 (2)0.052 (2)0.047 (2)0.0069 (18)0.0228 (18)0.0029 (17)
C200.094 (3)0.054 (3)0.072 (3)−0.013 (2)0.041 (2)−0.013 (2)
C210.167 (5)0.066 (3)0.091 (4)0.056 (4)0.015 (4)−0.008 (3)
C220.105 (4)0.093 (4)0.078 (3)−0.014 (3)0.030 (3)−0.035 (3)
C230.075 (3)0.040 (2)0.074 (3)−0.0032 (19)0.034 (2)0.004 (2)
C240.077 (3)0.052 (3)0.087 (3)−0.014 (2)0.030 (2)0.004 (2)
C250.087 (4)0.119 (5)0.116 (4)−0.041 (3)0.001 (3)0.011 (4)
C260.109 (4)0.053 (3)0.186 (6)−0.014 (3)0.061 (4)0.024 (3)
F10.0994 (18)0.0704 (17)0.0828 (17)−0.0229 (14)0.0160 (14)−0.0294 (14)
F20.0789 (16)0.0622 (16)0.120 (2)0.0124 (13)−0.0038 (15)0.0095 (15)
F30.105 (2)0.089 (2)0.103 (2)−0.0209 (16)0.0388 (16)0.0105 (16)
F40.142 (3)0.0577 (16)0.096 (2)−0.0114 (16)0.0059 (17)−0.0290 (15)
F50.0843 (18)0.0725 (18)0.139 (2)0.0210 (14)0.0074 (17)0.0211 (17)
F60.128 (2)0.0788 (19)0.105 (2)0.0015 (17)0.0616 (18)0.0080 (16)
P10.0508 (5)0.0438 (6)0.0477 (5)−0.0007 (4)0.0179 (4)−0.0006 (4)
P20.0546 (5)0.0429 (6)0.0472 (5)0.0024 (4)0.0188 (4)0.0008 (4)
P30.0628 (6)0.0361 (6)0.0614 (6)−0.0009 (5)0.0081 (5)−0.0028 (5)

Geometric parameters (Å, °)

Co1—C162.028 (3)C13—H13B0.9600
Co1—C22.028 (3)C13—H13C0.9600
Co1—C182.033 (3)C14—C151.430 (4)
Co1—C172.034 (3)C14—C181.433 (4)
Co1—C152.036 (3)C14—P21.823 (3)
Co1—C52.038 (3)C15—C161.407 (5)
Co1—C12.041 (3)C15—H150.9800
Co1—C32.045 (3)C16—C171.403 (5)
Co1—C42.053 (3)C16—H160.9800
Co1—C142.056 (3)C17—C181.410 (5)
C1—C51.431 (5)C17—H170.9800
C1—C21.437 (4)C18—H180.9800
C1—P11.824 (3)C19—C201.515 (5)
C2—C31.415 (5)C19—P21.850 (3)
C2—H20.9800C19—H19A0.9700
C3—C41.413 (5)C19—H19B0.9700
C3—H30.9800C20—C211.515 (6)
C4—C51.421 (5)C20—C221.532 (5)
C4—H40.9800C20—H200.9800
C5—H50.9800C21—H21A0.9600
C6—C71.513 (5)C21—H21B0.9600
C6—P11.845 (4)C21—H21C0.9600
C6—H6A0.9700C22—H22A0.9600
C6—H6B0.9700C22—H22B0.9600
C7—C81.508 (6)C22—H22C0.9600
C7—C91.530 (6)C23—C241.519 (5)
C7—H70.9800C23—P21.850 (4)
C8—H8A0.9600C23—H23A0.9700
C8—H8B0.9600C23—H23B0.9700
C8—H8C0.9600C24—C251.487 (6)
C9—H9A0.9600C24—C261.527 (6)
C9—H9B0.9600C24—H240.9800
C9—H9C0.9600C25—H25A0.9600
C10—C111.523 (5)C25—H25B0.9600
C10—P11.851 (4)C25—H25C0.9600
C10—H10A0.9700C26—H26A0.9600
C10—H10B0.9700C26—H26B0.9600
C11—C131.512 (6)C26—H26C0.9600
C11—C121.526 (5)F1—P31.586 (2)
C11—H110.9800F2—P31.585 (2)
C12—H12A0.9600F3—P31.579 (3)
C12—H12B0.9600F4—P31.584 (2)
C12—H12C0.9600F5—P31.576 (2)
C13—H13A0.9600F6—P31.585 (3)
C16—Co1—C2109.48 (15)C11—C12—H12A109.5
C16—Co1—C1868.21 (15)C11—C12—H12B109.5
C2—Co1—C18176.26 (14)H12A—C12—H12B109.5
C16—Co1—C1740.40 (14)C11—C12—H12C109.5
C2—Co1—C17135.80 (16)H12A—C12—H12C109.5
C18—Co1—C1740.57 (14)H12B—C12—H12C109.5
C16—Co1—C1540.50 (13)C11—C13—H13A109.5
C2—Co1—C15112.05 (14)C11—C13—H13B109.5
C18—Co1—C1568.31 (14)H13A—C13—H13B109.5
C17—Co1—C1568.08 (15)C11—C13—H13C109.5
C16—Co1—C5141.94 (15)H13A—C13—H13C109.5
C2—Co1—C568.72 (14)H13B—C13—H13C109.5
C18—Co1—C5111.10 (14)C15—C14—C18105.9 (3)
C17—Co1—C5113.26 (15)C15—C14—P2130.1 (3)
C15—Co1—C5177.38 (13)C18—C14—P2124.0 (3)
C16—Co1—C1111.52 (14)C15—C14—Co168.81 (18)
C2—Co1—C141.36 (12)C18—C14—Co168.62 (18)
C18—Co1—C1136.13 (13)P2—C14—Co1126.59 (17)
C17—Co1—C1109.39 (14)C16—C15—C14108.8 (3)
C15—Co1—C1141.09 (13)C16—C15—Co169.44 (19)
C5—Co1—C141.07 (13)C14—C15—Co170.28 (18)
C16—Co1—C3136.09 (16)C16—C15—H15125.6
C2—Co1—C340.66 (14)C14—C15—H15125.6
C18—Co1—C3143.01 (15)Co1—C15—H15125.6
C17—Co1—C3175.89 (16)C17—C16—C15108.4 (3)
C15—Co1—C3110.47 (15)C17—C16—Co170.0 (2)
C5—Co1—C368.35 (15)C15—C16—Co170.07 (19)
C1—Co1—C369.14 (13)C17—C16—H16125.8
C16—Co1—C4176.30 (16)C15—C16—H16125.8
C2—Co1—C468.30 (14)Co1—C16—H16125.8
C18—Co1—C4114.16 (15)C16—C17—C18108.1 (3)
C17—Co1—C4143.21 (16)C16—C17—Co169.6 (2)
C15—Co1—C4136.99 (15)C18—C17—Co169.65 (19)
C5—Co1—C440.65 (13)C16—C17—H17126.0
C1—Co1—C468.97 (14)C18—C17—H17126.0
C3—Co1—C440.35 (14)Co1—C17—H17126.0
C16—Co1—C1468.80 (14)C17—C18—C14108.8 (3)
C2—Co1—C14141.54 (13)C17—C18—Co169.8 (2)
C18—Co1—C1441.02 (12)C14—C18—Co170.36 (18)
C17—Co1—C1468.82 (14)C17—C18—H18125.6
C15—Co1—C1440.91 (12)C14—C18—H18125.6
C5—Co1—C14137.02 (13)Co1—C18—H18125.6
C1—Co1—C14177.04 (13)C20—C19—P2116.2 (3)
C3—Co1—C14112.82 (14)C20—C19—H19A108.2
C4—Co1—C14110.91 (14)P2—C19—H19A108.2
C5—C1—C2106.3 (3)C20—C19—H19B108.2
C5—C1—P1130.4 (3)P2—C19—H19B108.2
C2—C1—P1123.3 (3)H19A—C19—H19B107.4
C5—C1—Co169.38 (19)C19—C20—C21112.4 (4)
C2—C1—Co168.86 (18)C19—C20—C22110.6 (4)
P1—C1—Co1124.48 (16)C21—C20—C22110.4 (4)
C3—C2—C1108.7 (3)C19—C20—H20107.8
C3—C2—Co170.3 (2)C21—C20—H20107.8
C1—C2—Co169.78 (18)C22—C20—H20107.8
C3—C2—H2125.6C20—C21—H21A109.5
C1—C2—H2125.6C20—C21—H21B109.5
Co1—C2—H2125.6H21A—C21—H21B109.5
C4—C3—C2108.2 (3)C20—C21—H21C109.5
C4—C3—Co170.16 (19)H21A—C21—H21C109.5
C2—C3—Co169.06 (19)H21B—C21—H21C109.5
C4—C3—H3125.9C20—C22—H22A109.5
C2—C3—H3125.9C20—C22—H22B109.5
Co1—C3—H3125.9H22A—C22—H22B109.5
C3—C4—C5108.0 (3)C20—C22—H22C109.5
C3—C4—Co169.49 (19)H22A—C22—H22C109.5
C5—C4—Co169.10 (18)H22B—C22—H22C109.5
C3—C4—H4126.0C24—C23—P2115.0 (3)
C5—C4—H4126.0C24—C23—H23A108.5
Co1—C4—H4126.0P2—C23—H23A108.5
C4—C5—C1108.7 (3)C24—C23—H23B108.5
C4—C5—Co170.25 (19)P2—C23—H23B108.5
C1—C5—Co169.55 (18)H23A—C23—H23B107.5
C4—C5—H5125.6C25—C24—C23113.7 (4)
C1—C5—H5125.6C25—C24—C26111.2 (4)
Co1—C5—H5125.6C23—C24—C26109.4 (4)
C7—C6—P1112.9 (3)C25—C24—H24107.4
C7—C6—H6A109.0C23—C24—H24107.4
P1—C6—H6A109.0C26—C24—H24107.4
C7—C6—H6B109.0C24—C25—H25A109.5
P1—C6—H6B109.0C24—C25—H25B109.5
H6A—C6—H6B107.8H25A—C25—H25B109.5
C8—C7—C6111.5 (4)C24—C25—H25C109.5
C8—C7—C9109.4 (4)H25A—C25—H25C109.5
C6—C7—C9110.8 (4)H25B—C25—H25C109.5
C8—C7—H7108.4C24—C26—H26A109.5
C6—C7—H7108.4C24—C26—H26B109.5
C9—C7—H7108.4H26A—C26—H26B109.5
C7—C8—H8A109.5C24—C26—H26C109.5
C7—C8—H8B109.5H26A—C26—H26C109.5
H8A—C8—H8B109.5H26B—C26—H26C109.5
C7—C8—H8C109.5C1—P1—C6101.32 (16)
H8A—C8—H8C109.5C1—P1—C1098.64 (16)
H8B—C8—H8C109.5C6—P1—C1099.83 (17)
C7—C9—H9A109.5C14—P2—C2399.00 (16)
C7—C9—H9B109.5C14—P2—C1998.79 (16)
H9A—C9—H9B109.5C23—P2—C1999.08 (18)
C7—C9—H9C109.5F5—P3—F389.92 (16)
H9A—C9—H9C109.5F5—P3—F490.45 (15)
H9B—C9—H9C109.5F3—P3—F489.63 (15)
C11—C10—P1115.8 (3)F5—P3—F689.95 (16)
C11—C10—H10A108.3F3—P3—F6179.69 (17)
P1—C10—H10A108.3F4—P3—F690.65 (16)
C11—C10—H10B108.3F5—P3—F2178.99 (18)
P1—C10—H10B108.3F3—P3—F291.09 (16)
H10A—C10—H10B107.4F4—P3—F289.53 (14)
C13—C11—C10112.2 (4)F6—P3—F289.04 (16)
C13—C11—C12110.9 (4)F5—P3—F190.58 (15)
C10—C11—C12110.1 (4)F3—P3—F190.94 (15)
C13—C11—H11107.8F4—P3—F1178.83 (16)
C10—C11—H11107.8F6—P3—F188.78 (14)
C12—C11—H11107.8F2—P3—F189.44 (14)
C16—Co1—C1—C5−146.7 (2)C15—Co1—C14—C18117.8 (3)
C2—Co1—C1—C5117.9 (3)C5—Co1—C14—C18−64.6 (3)
C18—Co1—C1—C5−66.2 (3)C3—Co1—C14—C18−146.8 (2)
C17—Co1—C1—C5−103.5 (2)C4—Co1—C14—C18−103.2 (2)
C15—Co1—C1—C5177.7 (2)C16—Co1—C14—P2−162.0 (3)
C3—Co1—C1—C580.6 (2)C2—Co1—C14—P2−67.1 (3)
C4—Co1—C1—C537.2 (2)C18—Co1—C14—P2117.2 (3)
C16—Co1—C1—C295.4 (2)C17—Co1—C14—P2154.5 (3)
C18—Co1—C1—C2175.9 (2)C15—Co1—C14—P2−125.0 (3)
C17—Co1—C1—C2138.6 (2)C5—Co1—C14—P252.6 (3)
C15—Co1—C1—C259.8 (3)C3—Co1—C14—P2−29.6 (3)
C5—Co1—C1—C2−117.9 (3)C4—Co1—C14—P214.0 (2)
C3—Co1—C1—C2−37.3 (2)C18—C14—C15—C160.0 (4)
C4—Co1—C1—C2−80.6 (2)P2—C14—C15—C16179.5 (2)
C16—Co1—C1—P1−21.2 (3)Co1—C14—C15—C1658.9 (2)
C2—Co1—C1—P1−116.6 (3)C18—C14—C15—Co1−58.9 (2)
C18—Co1—C1—P159.3 (3)P2—C14—C15—Co1120.6 (3)
C17—Co1—C1—P122.0 (3)C2—Co1—C15—C1694.6 (2)
C15—Co1—C1—P1−56.8 (3)C18—Co1—C15—C16−81.4 (2)
C5—Co1—C1—P1125.5 (3)C17—Co1—C15—C16−37.5 (2)
C3—Co1—C1—P1−153.9 (3)C1—Co1—C15—C1656.5 (3)
C4—Co1—C1—P1162.8 (2)C3—Co1—C15—C16138.3 (2)
C5—C1—C2—C30.2 (4)C4—Co1—C15—C16175.9 (2)
P1—C1—C2—C3177.9 (2)C14—Co1—C15—C16−120.1 (3)
Co1—C1—C2—C359.7 (2)C16—Co1—C15—C14120.1 (3)
C5—C1—C2—Co1−59.6 (2)C2—Co1—C15—C14−145.4 (2)
P1—C1—C2—Co1118.2 (2)C18—Co1—C15—C1438.66 (19)
C16—Co1—C2—C3139.5 (2)C17—Co1—C15—C1482.5 (2)
C17—Co1—C2—C3176.9 (2)C1—Co1—C15—C14176.6 (2)
C15—Co1—C2—C396.2 (2)C3—Co1—C15—C14−101.6 (2)
C5—Co1—C2—C3−81.1 (2)C4—Co1—C15—C14−64.0 (3)
C1—Co1—C2—C3−119.7 (3)C14—C15—C16—C170.4 (4)
C4—Co1—C2—C3−37.3 (2)Co1—C15—C16—C1759.8 (2)
C14—Co1—C2—C359.4 (3)C14—C15—C16—Co1−59.4 (2)
C16—Co1—C2—C1−100.8 (2)C2—Co1—C16—C17139.3 (2)
C17—Co1—C2—C1−63.4 (3)C18—Co1—C16—C17−37.6 (2)
C15—Co1—C2—C1−144.14 (19)C15—Co1—C16—C17−119.3 (3)
C5—Co1—C2—C138.55 (19)C5—Co1—C16—C1759.2 (3)
C3—Co1—C2—C1119.7 (3)C1—Co1—C16—C1795.0 (2)
C4—Co1—C2—C182.4 (2)C3—Co1—C16—C17176.8 (2)
C14—Co1—C2—C1179.09 (19)C14—Co1—C16—C17−81.8 (2)
C1—C2—C3—C40.0 (4)C2—Co1—C16—C15−101.5 (2)
Co1—C2—C3—C459.4 (2)C18—Co1—C16—C1581.7 (2)
C1—C2—C3—Co1−59.4 (2)C17—Co1—C16—C15119.3 (3)
C16—Co1—C3—C4178.5 (2)C5—Co1—C16—C15178.5 (2)
C2—Co1—C3—C4−119.6 (3)C1—Co1—C16—C15−145.7 (2)
C18—Co1—C3—C459.2 (3)C3—Co1—C16—C15−63.9 (3)
C15—Co1—C3—C4140.0 (2)C14—Co1—C16—C1537.4 (2)
C5—Co1—C3—C4−37.5 (2)C15—C16—C17—C18−0.6 (4)
C1—Co1—C3—C4−81.7 (2)Co1—C16—C17—C1859.2 (2)
C14—Co1—C3—C495.9 (2)C15—C16—C17—Co1−59.8 (2)
C16—Co1—C3—C2−61.9 (3)C2—Co1—C17—C16−62.0 (3)
C18—Co1—C3—C2178.8 (2)C18—Co1—C17—C16119.4 (3)
C15—Co1—C3—C2−100.4 (2)C15—Co1—C17—C1637.6 (2)
C5—Co1—C3—C282.1 (2)C5—Co1—C17—C16−144.8 (2)
C1—Co1—C3—C237.9 (2)C1—Co1—C17—C16−100.7 (2)
C4—Co1—C3—C2119.6 (3)C4—Co1—C17—C16178.7 (2)
C14—Co1—C3—C2−144.5 (2)C14—Co1—C17—C1681.8 (2)
C2—C3—C4—C5−0.2 (4)C16—Co1—C17—C18−119.4 (3)
Co1—C3—C4—C558.5 (2)C2—Co1—C17—C18178.6 (2)
C2—C3—C4—Co1−58.7 (2)C15—Co1—C17—C18−81.8 (2)
C2—Co1—C4—C337.6 (2)C5—Co1—C17—C1895.8 (2)
C18—Co1—C4—C3−145.5 (2)C1—Co1—C17—C18139.8 (2)
C17—Co1—C4—C3176.7 (2)C4—Co1—C17—C1859.3 (3)
C15—Co1—C4—C3−62.0 (3)C14—Co1—C17—C18−37.7 (2)
C5—Co1—C4—C3119.7 (3)C16—C17—C18—C140.6 (4)
C1—Co1—C4—C382.1 (2)Co1—C17—C18—C1459.7 (2)
C14—Co1—C4—C3−101.0 (2)C16—C17—C18—Co1−59.1 (2)
C2—Co1—C4—C5−82.2 (2)C15—C14—C18—C17−0.4 (4)
C18—Co1—C4—C594.8 (2)P2—C14—C18—C17−179.9 (2)
C17—Co1—C4—C557.0 (3)Co1—C14—C18—C17−59.4 (2)
C15—Co1—C4—C5178.3 (2)C15—C14—C18—Co159.0 (2)
C1—Co1—C4—C5−37.6 (2)P2—C14—C18—Co1−120.5 (2)
C3—Co1—C4—C5−119.7 (3)C16—Co1—C18—C1737.4 (2)
C14—Co1—C4—C5139.2 (2)C15—Co1—C18—C1781.2 (2)
C3—C4—C5—C10.3 (4)C5—Co1—C18—C17−101.6 (2)
Co1—C4—C5—C159.1 (2)C1—Co1—C18—C17−61.4 (3)
C3—C4—C5—Co1−58.8 (2)C3—Co1—C18—C17176.8 (3)
C2—C1—C5—C4−0.3 (4)C4—Co1—C18—C17−145.6 (2)
P1—C1—C5—C4−177.8 (2)C14—Co1—C18—C17119.7 (3)
Co1—C1—C5—C4−59.5 (2)C16—Co1—C18—C14−82.3 (2)
C2—C1—C5—Co159.2 (2)C17—Co1—C18—C14−119.7 (3)
P1—C1—C5—Co1−118.3 (3)C15—Co1—C18—C14−38.56 (19)
C16—Co1—C5—C4175.8 (2)C5—Co1—C18—C14138.70 (19)
C2—Co1—C5—C481.1 (2)C1—Co1—C18—C14178.82 (18)
C18—Co1—C5—C4−103.0 (2)C3—Co1—C18—C1457.0 (3)
C17—Co1—C5—C4−146.9 (2)C4—Co1—C18—C1494.6 (2)
C1—Co1—C5—C4119.9 (3)P2—C19—C20—C2161.7 (5)
C3—Co1—C5—C437.2 (2)P2—C19—C20—C22−174.4 (3)
C14—Co1—C5—C4−63.5 (3)P2—C23—C24—C2561.3 (5)
C16—Co1—C5—C156.0 (3)P2—C23—C24—C26−173.6 (3)
C2—Co1—C5—C1−38.82 (19)C5—C1—P1—C64.9 (3)
C18—Co1—C5—C1137.2 (2)C2—C1—P1—C6−172.2 (3)
C17—Co1—C5—C193.2 (2)Co1—C1—P1—C6−86.4 (2)
C3—Co1—C5—C1−82.7 (2)C5—C1—P1—C10−97.0 (3)
C4—Co1—C5—C1−119.9 (3)C2—C1—P1—C1085.8 (3)
C14—Co1—C5—C1176.62 (19)Co1—C1—P1—C10171.7 (2)
P1—C6—C7—C8−67.0 (5)C7—C6—P1—C1171.4 (3)
P1—C6—C7—C9171.0 (3)C7—C6—P1—C10−87.7 (3)
P1—C10—C11—C13−59.7 (5)C11—C10—P1—C1−70.1 (3)
P1—C10—C11—C12176.3 (3)C11—C10—P1—C6−173.2 (3)
C16—Co1—C14—C15−37.1 (2)C15—C14—P2—C23−0.1 (3)
C2—Co1—C14—C1557.9 (3)C18—C14—P2—C23179.4 (3)
C18—Co1—C14—C15−117.8 (3)Co1—C14—P2—C2392.0 (2)
C17—Co1—C14—C15−80.5 (2)C15—C14—P2—C19100.6 (3)
C5—Co1—C14—C15177.6 (2)C18—C14—P2—C19−79.9 (3)
C3—Co1—C14—C1595.4 (2)Co1—C14—P2—C19−167.2 (2)
C4—Co1—C14—C15139.0 (2)C24—C23—P2—C14179.3 (3)
C16—Co1—C14—C1880.7 (2)C24—C23—P2—C1978.8 (3)
C2—Co1—C14—C18175.7 (2)C20—C19—P2—C1481.0 (3)
C17—Co1—C14—C1837.3 (2)C20—C19—P2—C23−178.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···F5i0.982.443.237 (5)138
C15—H15···F4i0.982.393.278 (4)150
C17—H17···F20.982.513.188 (5)126
C18—H18···F60.982.413.305 (4)152
C19—H19B···F2ii0.972.543.494 (4)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2295).

References

  • Brasse, C. C., Englert, U., Salzer, A., Waffenschmidt, H. & Wasserscheid, P. (2000). Organmetallics, 19, 3818-3823.
  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hou, J.-G., Zhang, P., Ye, C. & Yu, T.-G. (2007). Acta Cryst. E63, m2730.
  • Mathews, C. J., Smith, P. J. & Welton, T. (2000). Chem. Commun. pp. 1249–1250.
  • Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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