metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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COMMUNICATIONS
ISSN: 2056-9890

1,1′-Bis(diiso­butyl­phosphino)cobalto­cenium hexa­fluorido­phosphate

aDepartment of Biotic Environment, Nanchang Institute of Technology, Nanchang 330013, People's Republic of China
*Correspondence e-mail: hjg0715@yahoo.com.cn

(Received 19 May 2008; accepted 7 June 2008; online 19 June 2008)

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 (10[\overline{1}]) plane.

Related literature

For background to cobaltocene derivatives applied as catal­ysts, see: Mathews et al. (2000[Mathews, C. J., Smith, P. J. & Welton, T. (2000). Chem. Commun. pp. 1249-1250.]). For the structures of closely related compounds, see: Brasse et al. (2000[Brasse, C. C., Englert, U., Salzer, A., Waffenschmidt, H. & Wasserscheid, P. (2000). Organmetallics, 19, 3818-3823.]); Hou et al. (2007[Hou, J.-G., Zhang, P., Ye, C. & Yu, T.-G. (2007). Acta Cryst. E63, m2730.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(C13H22P)2]·PF6

  • Mr = 622.45

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.750, Tmax = 0.985

  • 33818 measured reflections

  • 6733 independent reflections

  • 3878 reflections with I > 2σ(I)

  • Rint = 0.083

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯F5i 0.98 2.44 3.237 (5) 138
C15—H15⋯F4i 0.98 2.39 3.278 (4) 150
C17—H17⋯F2 0.98 2.51 3.188 (5) 126
C18—H18⋯F6 0.98 2.41 3.305 (4) 152
C19—H19B⋯F2ii 0.97 2.54 3.494 (4) 167
Symmetry codes: (i) x, y-1, z; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing ellipsoids at 30% probability level.
[Figure 2] 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.
1,1'-Bis(diisobutylphosphino)cobaltocenium hexafluorophosphate top
Crystal data top
[Co(C13H22P)2]·PF6F(000) = 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 = 2.3–19.9°
b = 10.4660 (2) ŵ = 0.76 mm1
c = 18.5105 (4) ÅT = 298 K
β = 108.288 (1)°Needle, yellow
V = 3085.38 (10) Å30.40 × 0.04 × 0.02 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
6733 independent reflections
Radiation source: fine-focus sealed tube3878 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
ϕ and ω scansθmax = 27.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 2121
Tmin = 0.750, Tmax = 0.985k = 1313
33818 measured reflectionsl = 2322
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0731P)2]
where P = (Fo2 + 2Fc2)/3
6733 reflections(Δ/σ)max = 0.001
333 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
[Co(C13H22P)2]·PF6V = 3085.38 (10) Å3
Mr = 622.45Z = 4
Monoclinic, P21/nMo Kα radiation
a = 16.7733 (3) ŵ = 0.76 mm1
b = 10.4660 (2) ÅT = 298 K
c = 18.5105 (4) Å0.40 × 0.04 × 0.02 mm
β = 108.288 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
6733 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
3878 reflections with I > 2σ(I)
Tmin = 0.750, Tmax = 0.985Rint = 0.083
33818 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 0.97Δρmax = 0.47 e Å3
6733 reflectionsΔρmin = 0.34 e Å3
333 parameters
Special details top

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) top
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)
H40.50470.37940.01930.065*
C50.6254 (2)0.4270 (3)0.02941 (18)0.0468 (9)
H50.62150.51890.04020.056*
C60.7928 (2)0.5658 (3)0.0360 (2)0.0558 (10)
H6A0.75260.58700.08490.067*
H6B0.77170.59930.00330.067*
C70.8757 (3)0.6294 (4)0.0295 (3)0.0740 (13)
H70.89980.58800.06550.089*
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)
H9A0.83790.81270.01640.166*
H9B0.82700.77980.10160.166*
H9C0.91640.80990.04510.166*
C100.7851 (2)0.3465 (4)0.1272 (2)0.0562 (10)
H10A0.73440.38820.15860.067*
H10B0.83160.38030.14190.067*
C110.7776 (3)0.2041 (4)0.1449 (2)0.0694 (12)
H110.73000.17100.13060.083*
C120.7589 (3)0.1826 (5)0.2301 (3)0.1059 (18)
H12A0.80420.21600.24580.159*
H12B0.70770.22560.25730.159*
H12C0.75300.09280.24090.159*
C130.8552 (4)0.1312 (4)0.1000 (3)0.1079 (19)
H13A0.85060.04400.11700.162*
H13B0.86030.13370.04690.162*
H13C0.90390.16950.10770.162*
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)
H26A0.43040.07610.25380.169*
H26B0.52690.04640.28320.169*
H26C0.48460.09100.19900.169*
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) top
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, º) top
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—C5146.7 (2)C15—Co1—C14—C18117.8 (3)
C2—Co1—C1—C5117.9 (3)C5—Co1—C14—C1864.6 (3)
C18—Co1—C1—C566.2 (3)C3—Co1—C14—C18146.8 (2)
C17—Co1—C1—C5103.5 (2)C4—Co1—C14—C18103.2 (2)
C15—Co1—C1—C5177.7 (2)C16—Co1—C14—P2162.0 (3)
C3—Co1—C1—C580.6 (2)C2—Co1—C14—P267.1 (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—P2125.0 (3)
C17—Co1—C1—C2138.6 (2)C5—Co1—C14—P252.6 (3)
C15—Co1—C1—C259.8 (3)C3—Co1—C14—P229.6 (3)
C5—Co1—C1—C2117.9 (3)C4—Co1—C14—P214.0 (2)
C3—Co1—C1—C237.3 (2)C18—C14—C15—C160.0 (4)
C4—Co1—C1—C280.6 (2)P2—C14—C15—C16179.5 (2)
C16—Co1—C1—P121.2 (3)Co1—C14—C15—C1658.9 (2)
C2—Co1—C1—P1116.6 (3)C18—C14—C15—Co158.9 (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—P156.8 (3)C18—Co1—C15—C1681.4 (2)
C5—Co1—C1—P1125.5 (3)C17—Co1—C15—C1637.5 (2)
C3—Co1—C1—P1153.9 (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—C16120.1 (3)
Co1—C1—C2—C359.7 (2)C16—Co1—C15—C14120.1 (3)
C5—C1—C2—Co159.6 (2)C2—Co1—C15—C14145.4 (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—C14101.6 (2)
C5—Co1—C2—C381.1 (2)C4—Co1—C15—C1464.0 (3)
C1—Co1—C2—C3119.7 (3)C14—C15—C16—C170.4 (4)
C4—Co1—C2—C337.3 (2)Co1—C15—C16—C1759.8 (2)
C14—Co1—C2—C359.4 (3)C14—C15—C16—Co159.4 (2)
C16—Co1—C2—C1100.8 (2)C2—Co1—C16—C17139.3 (2)
C17—Co1—C2—C163.4 (3)C18—Co1—C16—C1737.6 (2)
C15—Co1—C2—C1144.14 (19)C15—Co1—C16—C17119.3 (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—C1781.8 (2)
C1—C2—C3—C40.0 (4)C2—Co1—C16—C15101.5 (2)
Co1—C2—C3—C459.4 (2)C18—Co1—C16—C1581.7 (2)
C1—C2—C3—Co159.4 (2)C17—Co1—C16—C15119.3 (3)
C16—Co1—C3—C4178.5 (2)C5—Co1—C16—C15178.5 (2)
C2—Co1—C3—C4119.6 (3)C1—Co1—C16—C15145.7 (2)
C18—Co1—C3—C459.2 (3)C3—Co1—C16—C1563.9 (3)
C15—Co1—C3—C4140.0 (2)C14—Co1—C16—C1537.4 (2)
C5—Co1—C3—C437.5 (2)C15—C16—C17—C180.6 (4)
C1—Co1—C3—C481.7 (2)Co1—C16—C17—C1859.2 (2)
C14—Co1—C3—C495.9 (2)C15—C16—C17—Co159.8 (2)
C16—Co1—C3—C261.9 (3)C2—Co1—C17—C1662.0 (3)
C18—Co1—C3—C2178.8 (2)C18—Co1—C17—C16119.4 (3)
C15—Co1—C3—C2100.4 (2)C15—Co1—C17—C1637.6 (2)
C5—Co1—C3—C282.1 (2)C5—Co1—C17—C16144.8 (2)
C1—Co1—C3—C237.9 (2)C1—Co1—C17—C16100.7 (2)
C4—Co1—C3—C2119.6 (3)C4—Co1—C17—C16178.7 (2)
C14—Co1—C3—C2144.5 (2)C14—Co1—C17—C1681.8 (2)
C2—C3—C4—C50.2 (4)C16—Co1—C17—C18119.4 (3)
Co1—C3—C4—C558.5 (2)C2—Co1—C17—C18178.6 (2)
C2—C3—C4—Co158.7 (2)C15—Co1—C17—C1881.8 (2)
C2—Co1—C4—C337.6 (2)C5—Co1—C17—C1895.8 (2)
C18—Co1—C4—C3145.5 (2)C1—Co1—C17—C18139.8 (2)
C17—Co1—C4—C3176.7 (2)C4—Co1—C17—C1859.3 (3)
C15—Co1—C4—C362.0 (3)C14—Co1—C17—C1837.7 (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—C3101.0 (2)C16—C17—C18—Co159.1 (2)
C2—Co1—C4—C582.2 (2)C15—C14—C18—C170.4 (4)
C18—Co1—C4—C594.8 (2)P2—C14—C18—C17179.9 (2)
C17—Co1—C4—C557.0 (3)Co1—C14—C18—C1759.4 (2)
C15—Co1—C4—C5178.3 (2)C15—C14—C18—Co159.0 (2)
C1—Co1—C4—C537.6 (2)P2—C14—C18—Co1120.5 (2)
C3—Co1—C4—C5119.7 (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—C17101.6 (2)
Co1—C4—C5—C159.1 (2)C1—Co1—C18—C1761.4 (3)
C3—C4—C5—Co158.8 (2)C3—Co1—C18—C17176.8 (3)
C2—C1—C5—C40.3 (4)C4—Co1—C18—C17145.6 (2)
P1—C1—C5—C4177.8 (2)C14—Co1—C18—C17119.7 (3)
Co1—C1—C5—C459.5 (2)C16—Co1—C18—C1482.3 (2)
C2—C1—C5—Co159.2 (2)C17—Co1—C18—C14119.7 (3)
P1—C1—C5—Co1118.3 (3)C15—Co1—C18—C1438.56 (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—C4103.0 (2)C3—Co1—C18—C1457.0 (3)
C17—Co1—C5—C4146.9 (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—C22174.4 (3)
C14—Co1—C5—C463.5 (3)P2—C23—C24—C2561.3 (5)
C16—Co1—C5—C156.0 (3)P2—C23—C24—C26173.6 (3)
C2—Co1—C5—C138.82 (19)C5—C1—P1—C64.9 (3)
C18—Co1—C5—C1137.2 (2)C2—C1—P1—C6172.2 (3)
C17—Co1—C5—C193.2 (2)Co1—C1—P1—C686.4 (2)
C3—Co1—C5—C182.7 (2)C5—C1—P1—C1097.0 (3)
C4—Co1—C5—C1119.9 (3)C2—C1—P1—C1085.8 (3)
C14—Co1—C5—C1176.62 (19)Co1—C1—P1—C10171.7 (2)
P1—C6—C7—C867.0 (5)C7—C6—P1—C1171.4 (3)
P1—C6—C7—C9171.0 (3)C7—C6—P1—C1087.7 (3)
P1—C10—C11—C1359.7 (5)C11—C10—P1—C170.1 (3)
P1—C10—C11—C12176.3 (3)C11—C10—P1—C6173.2 (3)
C16—Co1—C14—C1537.1 (2)C15—C14—P2—C230.1 (3)
C2—Co1—C14—C1557.9 (3)C18—C14—P2—C23179.4 (3)
C18—Co1—C14—C15117.8 (3)Co1—C14—P2—C2392.0 (2)
C17—Co1—C14—C1580.5 (2)C15—C14—P2—C19100.6 (3)
C5—Co1—C14—C15177.6 (2)C18—C14—P2—C1979.9 (3)
C3—Co1—C14—C1595.4 (2)Co1—C14—P2—C19167.2 (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—C23178.3 (3)
Hydrogen-bond geometry (Å, º) top
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, y1, z; (ii) x+3/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Co(C13H22P)2]·PF6
Mr622.45
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)16.7733 (3), 10.4660 (2), 18.5105 (4)
β (°) 108.288 (1)
V3)3085.38 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.76
Crystal size (mm)0.40 × 0.04 × 0.02
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.750, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
33818, 6733, 3878
Rint0.083
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.147, 0.97
No. of reflections6733
No. of parameters333
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.47, 0.34

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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, y1, z; (ii) x+3/2, y1/2, z+1/2.
 

Acknowledgements

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).

References

First citationBrasse, C. C., Englert, U., Salzer, A., Waffenschmidt, H. & Wasserscheid, P. (2000). Organmetallics, 19, 3818-3823.  Web of Science CrossRef CAS Google Scholar
First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHou, J.-G., Zhang, P., Ye, C. & Yu, T.-G. (2007). Acta Cryst. E63, m2730.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMathews, C. J., Smith, P. J. & Welton, T. (2000). Chem. Commun. pp. 1249–1250.  Web of Science CrossRef Google Scholar
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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