Chlorido[1-(diphenyl­phosphan­yl)cobaltocenium]gold(I) hexa­fluoridophosphate

Wu, X.-H.

doi:10.1107/S1600536811018769

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m798

doi:10.1107/S1600536811018769

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Chlorido[1-(diphenylphosphanyl)cobaltocenium]gold(I) hexafluoridophosphate

Xiang-Hua Wu ^a ^*

^aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650092, People's Republic of China
^*Correspondence e-mail: chxhwu@yahoo.cn

(Received 17 April 2011; accepted 17 May 2011; online 25 May 2011)

In the cobaltocenium group of the title compound, [AuCo(C₅H₅)(C₁₇H₁₄P)Cl]PF₆, the substituted cyclopentadienyl (Cps) and the unsubstituted cyclopentadienyl (Cp) ring planes are almost parallel, making a dihedral angle of 3.1 (3)°. The C atoms in Cp and Cps are in an eclipsed conformation. The Au^I atom is coordinated by a P atom from the diphenylphosphanyl group and a Cl atom in an almost linear arrangement [P—Au—Cl = 178.15–(7)°]. Two hexafluoridophosphate anions are each located on a twofold rotation axis. In the crystal, the complex cations and hexafluoridophosphate anions are linked via intermolecular C—H⋯F hydrogen bonds.

Related literature

For a related structure, see: Chen et al. (2009 ).

Experimental

Crystal data

[AuCo(C₅H₅)(C₁₇H₁₄P)Cl]PF₆
M_r = 750.66
Monoclinic, C 2/c
a = 11.5565 (14) Å
b = 14.8537 (14) Å
c = 27.983 (3) Å
β = 97.577 (2)°
V = 4761.6 (9) Å³
Z = 8
Mo Kα radiation
μ = 7.15 mm⁻¹
T = 292 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEX CCD diffractometer
24437 measured reflections
4680 independent reflections
4190 reflections with I > 2σ(I)
R_int = 0.183

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.125
S = 1.06
4680 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 3.36 e Å⁻³
Δρ_min = −1.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯F5ⁱ	0.98	2.56	3.249 (11)	128
C8—H8⋯F4ⁱ	0.98	2.41	3.090 (10)	126
C10—H10⋯F8ⁱ	0.98	2.53	3.185 (12)	125
Symmetry code: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018769/hy2423sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018769/hy2423Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1. In the cobaltocenium moiety (Chen et al., 2009), two cyclopentadienyl rings are nearly parallel to each other with a dihedral angle at 3.1 (3)°. The C atoms of the substituted cyclopentadienyl (Cps) ring and the unsubstituted cyclopentadienyl (Cp) ring are in an eclipsed conformation. The Co1 atom is slightly nearer to the Cps plane, with the Co1—Cgs and Co1—Cg distances of 1.6275 (6) and 1.6323 (6) Å (Cgs and Cg are the centroids of the Cps and Cp rings). The Cgs—Co1—Cg angle is 177.06 (2)°. The P1, Au1 and Cl1 atoms are almost in a line, with an angle of 178.15 (7)°. The C1—P1—Au1 angle is 113.37 (18)°. The complex cations and hexafluorophosphate anions are linked by C—H···F hydrogen bonds (Table 1), as shown in Fig. 2.

Related literature top

For a related structure, see: Chen et al. (2009).

Experimental top

To a solution of 1-(diphenylphosphanyl)cobaltocenium hexafluorophosphate (5.18 g, 0.01 mol) in dichloromethane (20 ml) was added gold chloride dimethylsulfane (0.62 g, 0.01 mol). The reaction mixture was stirred at room temperature for 30 min. After removing the solvent under reduced pressure, the residue was collected and dried in a vacuum desiccator (yield: 84%, 84 mg). Crystals suitable for X-ray data collection were obtained by slow evaporation from a dichloromethane and hexane solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. [Symmetry codes: (i) 1-x, y, 1/2-z; (ii) -x, y, 1/2-z.]
	Fig. 2. Crystal packing of the title compound, showing intermolecular C—H···F hydrogen bonds (dashed lines).

Chlorido[1-(diphenylphosphanyl)cobaltocenium]gold(I) hexafluoridophosphate top

Crystal data top

[AuCo(C₅H₅)(C₁₇H₁₄P)Cl]PF₆	F(000) = 2864
M_r = 750.66	D_x = 2.094 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5908 reflections
a = 11.5565 (14) Å	θ = 2.2–27.5°
b = 14.8537 (14) Å	µ = 7.15 mm⁻¹
c = 27.983 (3) Å	T = 292 K
β = 97.577 (2)°	Block, colorless
V = 4761.6 (9) Å³	0.20 × 0.20 × 0.20 mm
Z = 8

Data collection top

Bruker APEX CCD diffractometer	4190 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.183
Graphite monochromator	θ_max = 26.0°, θ_min = 2.3°
ϕ and ω scans	h = −14→14
24437 measured reflections	k = −18→18
4680 independent reflections	l = −34→34

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0706P)²] where P = (F_o² + 2F_c²)/3
4680 reflections	(Δ/σ)_max = 0.001
301 parameters	Δρ_max = 3.36 e Å⁻³
0 restraints	Δρ_min = −1.59 e Å⁻³

Crystal data top

[AuCo(C₅H₅)(C₁₇H₁₄P)Cl]PF₆	V = 4761.6 (9) Å³
M_r = 750.66	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 11.5565 (14) Å	µ = 7.15 mm⁻¹
b = 14.8537 (14) Å	T = 292 K
c = 27.983 (3) Å	0.20 × 0.20 × 0.20 mm
β = 97.577 (2)°

Data collection top

Bruker APEX CCD diffractometer	4190 reflections with I > 2σ(I)
24437 measured reflections	R_int = 0.183
4680 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.06	Δρ_max = 3.36 e Å⁻³
4680 reflections	Δρ_min = −1.59 e Å⁻³
301 parameters

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

	x	y	z	U_iso*/U_eq
Au1	0.611737 (18)	0.111894 (15)	0.447818 (8)	0.04121 (13)
Cl1	0.6800 (2)	−0.02937 (13)	0.46391 (9)	0.0810 (6)
Co1	0.73961 (6)	0.31564 (5)	0.35937 (2)	0.0373 (2)
C1	0.6515 (4)	0.3281 (4)	0.41722 (19)	0.0353 (11)
C2	0.7751 (5)	0.3201 (4)	0.43184 (19)	0.0447 (13)
H2	0.8134	0.2725	0.4524	0.054*
C3	0.8318 (6)	0.3916 (5)	0.4118 (3)	0.0575 (19)
H3	0.9161	0.4026	0.4157	0.069*
C4	0.7441 (6)	0.4448 (5)	0.3837 (3)	0.0575 (17)
H4	0.7581	0.4984	0.3649	0.069*
C5	0.6348 (6)	0.4054 (4)	0.3868 (2)	0.0450 (13)
H5	0.5597	0.4273	0.3707	0.054*
C6	0.6927 (8)	0.1995 (6)	0.3237 (3)	0.070 (2)
H6	0.6433	0.1519	0.3345	0.084*
C7	0.8171 (8)	0.2057 (7)	0.3344 (3)	0.078 (2)
H7	0.8690	0.1631	0.3535	0.094*
C8	0.8503 (9)	0.2842 (7)	0.3112 (3)	0.088 (3)
H8	0.9301	0.3066	0.3116	0.105*
C9	0.7472 (9)	0.3263 (6)	0.2884 (2)	0.077 (2)
H9	0.7434	0.3823	0.2697	0.092*
C10	0.6548 (7)	0.2734 (7)	0.2960 (2)	0.070 (2)
H10	0.5730	0.2868	0.2842	0.084*
C11	0.5027 (4)	0.3014 (4)	0.48858 (17)	0.0323 (10)
C12	0.4193 (6)	0.2539 (5)	0.5115 (2)	0.0525 (15)
H12	0.3858	0.2012	0.4981	0.063*
C13	0.3884 (6)	0.2873 (7)	0.5542 (2)	0.061 (2)
H13	0.3328	0.2569	0.5693	0.074*
C14	0.4375 (7)	0.3633 (6)	0.5745 (2)	0.0592 (17)
H14	0.4159	0.3841	0.6034	0.071*
C15	0.5198 (7)	0.4102 (5)	0.5526 (3)	0.0603 (17)
H15	0.5537	0.4622	0.5667	0.072*
C16	0.5513 (6)	0.3789 (4)	0.5092 (2)	0.0436 (14)
H16	0.6056	0.4106	0.4941	0.052*
C17	0.4166 (4)	0.2607 (4)	0.38938 (18)	0.0347 (11)
C18	0.3477 (5)	0.3373 (5)	0.3875 (2)	0.0467 (14)
H18	0.3665	0.3843	0.4090	0.056*
C19	0.2490 (6)	0.3428 (6)	0.3524 (2)	0.0552 (17)
H19	0.2033	0.3945	0.3500	0.066*
C20	0.2205 (5)	0.2720 (6)	0.3221 (2)	0.0576 (19)
H20	0.1534	0.2752	0.2998	0.069*
C21	0.2892 (6)	0.1958 (6)	0.3239 (2)	0.0600 (18)
H21	0.2698	0.1490	0.3022	0.072*
C22	0.3869 (5)	0.1890 (5)	0.3580 (2)	0.0473 (14)
H22	0.4325	0.1372	0.3599	0.057*
F1	0.4729 (11)	0.0040 (5)	0.3031 (3)	0.183 (5)
F2	0.5000	0.1112 (4)	0.2500	0.093 (3)
F3	0.6304 (5)	0.0048 (5)	0.2686 (4)	0.168 (4)
F4	0.5000	−0.1023 (4)	0.2500	0.094 (3)
F5	0.0244 (12)	0.0474 (7)	0.3049 (3)	0.210 (5)
F6	0.1298 (5)	0.0463 (7)	0.2511 (5)	0.226 (6)
F7	0.0000	0.1482 (7)	0.2500	0.122 (3)
F8	0.0000	−0.0631 (6)	0.2500	0.201 (7)
P1	0.54402 (11)	0.25078 (9)	0.43452 (5)	0.0318 (3)
P2	0.5000	0.00498 (18)	0.2500	0.0579 (6)
P3	0.0000	0.0412 (2)	0.2500	0.0599 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.04551 (17)	0.02754 (19)	0.05013 (19)	0.00192 (8)	0.00461 (11)	0.00108 (8)
Cl1	0.0891 (13)	0.0334 (10)	0.1220 (17)	0.0148 (9)	0.0195 (12)	0.0106 (10)
Co1	0.0351 (4)	0.0411 (5)	0.0363 (4)	0.0013 (3)	0.0067 (3)	0.0021 (3)
C1	0.036 (3)	0.030 (3)	0.039 (3)	−0.006 (2)	0.004 (2)	0.000 (2)
C2	0.042 (3)	0.056 (4)	0.034 (3)	−0.006 (3)	−0.005 (2)	−0.002 (2)
C3	0.045 (3)	0.067 (5)	0.060 (4)	−0.020 (3)	0.004 (3)	−0.006 (3)
C4	0.072 (4)	0.036 (4)	0.068 (4)	−0.010 (3)	0.024 (3)	0.001 (3)
C5	0.046 (3)	0.032 (3)	0.058 (3)	0.003 (2)	0.011 (3)	0.001 (3)
C6	0.105 (6)	0.054 (5)	0.054 (4)	−0.008 (4)	0.026 (4)	−0.020 (3)
C7	0.103 (7)	0.073 (6)	0.062 (4)	0.034 (5)	0.021 (4)	−0.011 (4)
C8	0.086 (6)	0.107 (8)	0.080 (5)	0.001 (5)	0.048 (5)	−0.026 (5)
C9	0.113 (7)	0.085 (6)	0.036 (3)	0.014 (5)	0.023 (4)	0.012 (4)
C10	0.077 (5)	0.091 (6)	0.039 (3)	−0.003 (4)	−0.008 (3)	−0.012 (4)
C11	0.031 (2)	0.033 (3)	0.034 (2)	0.000 (2)	0.0061 (19)	0.004 (2)
C12	0.053 (3)	0.059 (4)	0.046 (3)	−0.018 (3)	0.007 (3)	0.001 (3)
C13	0.061 (4)	0.078 (6)	0.050 (4)	−0.012 (3)	0.026 (3)	0.004 (3)
C14	0.068 (4)	0.066 (5)	0.047 (3)	0.014 (4)	0.023 (3)	−0.001 (3)
C15	0.079 (5)	0.044 (4)	0.058 (4)	0.004 (4)	0.009 (3)	−0.014 (3)
C16	0.056 (4)	0.035 (3)	0.042 (3)	0.001 (2)	0.014 (3)	0.001 (2)
C17	0.031 (2)	0.037 (3)	0.035 (2)	−0.003 (2)	0.0009 (19)	0.005 (2)
C18	0.042 (3)	0.045 (4)	0.051 (3)	0.001 (3)	−0.002 (2)	0.006 (3)
C19	0.042 (3)	0.065 (5)	0.057 (4)	0.012 (3)	−0.002 (3)	0.012 (3)
C20	0.035 (3)	0.098 (6)	0.038 (3)	−0.010 (3)	−0.003 (2)	0.010 (3)
C21	0.051 (4)	0.078 (5)	0.049 (3)	−0.021 (4)	−0.002 (3)	−0.009 (3)
C22	0.049 (3)	0.050 (4)	0.042 (3)	−0.009 (3)	0.003 (2)	−0.006 (3)
F1	0.356 (15)	0.085 (5)	0.129 (6)	0.025 (6)	0.108 (8)	−0.006 (4)
F2	0.094 (5)	0.045 (5)	0.127 (6)	0.000	−0.028 (5)	0.000
F3	0.070 (4)	0.088 (5)	0.328 (13)	0.000 (3)	−0.046 (6)	0.005 (6)
F4	0.102 (5)	0.039 (4)	0.152 (7)	0.000	0.059 (5)	0.000
F5	0.352 (15)	0.172 (10)	0.089 (5)	−0.019 (10)	−0.031 (7)	0.032 (5)
F6	0.061 (4)	0.173 (9)	0.439 (18)	−0.007 (4)	0.017 (7)	−0.151 (10)
F7	0.139 (8)	0.070 (6)	0.150 (8)	0.000	−0.009 (7)	0.000
F8	0.164 (9)	0.044 (5)	0.354 (19)	0.000	−0.116 (11)	0.000
P1	0.0328 (6)	0.0276 (7)	0.0340 (6)	−0.0005 (5)	0.0009 (5)	0.0011 (5)
P2	0.0468 (12)	0.0389 (14)	0.0854 (18)	0.000	−0.0007 (12)	0.000
P3	0.0431 (12)	0.0567 (17)	0.0755 (16)	0.000	−0.0085 (11)	0.000

Geometric parameters (Å, º) top

Au1—P1	2.2203 (14)	C11—P1	1.809 (5)
Au1—Cl1	2.2657 (18)	C12—C13	1.384 (9)
Co1—C9	2.005 (6)	C12—H12	0.9300
Co1—C10	2.010 (7)	C13—C14	1.354 (12)
Co1—C2	2.017 (5)	C13—H13	0.9300
Co1—C5	2.020 (6)	C14—C15	1.386 (11)
Co1—C7	2.030 (8)	C14—H14	0.9300
Co1—C6	2.030 (8)	C15—C16	1.392 (9)
Co1—C8	2.031 (7)	C15—H15	0.9300
Co1—C1	2.031 (5)	C16—H16	0.9300
Co1—C4	2.033 (7)	C17—C18	1.386 (8)
Co1—C3	2.037 (7)	C17—C22	1.394 (8)
C1—C5	1.426 (8)	C17—P1	1.815 (5)
C1—C2	1.437 (8)	C18—C19	1.404 (9)
C1—P1	1.805 (5)	C18—H18	0.9300
C2—C3	1.404 (9)	C19—C20	1.364 (11)
C2—H2	0.9800	C19—H19	0.9300
C3—C4	1.434 (11)	C20—C21	1.381 (11)
C3—H3	0.9800	C20—H20	0.9300
C4—C5	1.404 (9)	C21—C22	1.382 (9)
C4—H4	0.9800	C21—H21	0.9300
C5—H5	0.9800	C22—H22	0.9300
C6—C10	1.383 (12)	F1—P2	1.557 (7)
C6—C7	1.432 (13)	F2—P2	1.577 (7)
C6—H6	0.9800	F3—P2	1.528 (6)
C7—C8	1.413 (13)	F4—P2	1.594 (7)
C7—H7	0.9800	F5—P3	1.527 (8)
C8—C9	1.420 (13)	F6—P3	1.498 (6)
C8—H8	0.9800	F7—P3	1.589 (11)
C9—C10	1.364 (12)	F8—P3	1.549 (9)
C9—H9	0.9800	P2—F3ⁱ	1.528 (6)
C10—H10	0.9800	P2—F1ⁱ	1.557 (7)
C11—C16	1.374 (8)	P3—F6ⁱⁱ	1.498 (6)
C11—C12	1.414 (7)	P3—F5ⁱⁱ	1.526 (8)

P1—Au1—Cl1	178.15 (7)	C7—C8—Co1	69.6 (4)
C9—Co1—C10	39.7 (4)	C9—C8—Co1	68.4 (4)
C9—Co1—C2	164.5 (3)	C7—C8—H8	126.0
C10—Co1—C2	155.3 (3)	C9—C8—H8	126.0
C9—Co1—C5	115.6 (3)	Co1—C8—H8	126.0
C10—Co1—C5	107.1 (3)	C10—C9—C8	107.7 (8)
C2—Co1—C5	69.4 (3)	C10—C9—Co1	70.3 (4)
C9—Co1—C7	69.2 (4)	C8—C9—Co1	70.4 (4)
C10—Co1—C7	68.4 (4)	C10—C9—H9	126.1
C2—Co1—C7	109.4 (3)	C8—C9—H9	126.1
C5—Co1—C7	167.3 (4)	Co1—C9—H9	126.1
C9—Co1—C6	67.9 (4)	C9—C10—C6	110.4 (8)
C10—Co1—C6	40.0 (4)	C9—C10—Co1	69.9 (4)
C2—Co1—C6	121.9 (3)	C6—C10—Co1	70.8 (4)
C5—Co1—C6	127.8 (3)	C9—C10—H10	124.8
C7—Co1—C6	41.3 (4)	C6—C10—H10	124.8
C9—Co1—C8	41.2 (4)	Co1—C10—H10	124.8
C10—Co1—C8	67.6 (4)	C16—C11—C12	119.5 (5)
C2—Co1—C8	127.8 (4)	C16—C11—P1	124.1 (4)
C5—Co1—C8	150.0 (4)	C12—C11—P1	116.3 (4)
C7—Co1—C8	40.7 (4)	C13—C12—C11	118.8 (6)
C6—Co1—C8	68.2 (4)	C13—C12—H12	120.6
C9—Co1—C1	150.9 (3)	C11—C12—H12	120.6
C10—Co1—C1	119.6 (3)	C14—C13—C12	121.2 (6)
C2—Co1—C1	41.6 (2)	C14—C13—H13	119.4
C5—Co1—C1	41.2 (2)	C12—C13—H13	119.4
C7—Co1—C1	129.6 (3)	C13—C14—C15	120.6 (6)
C6—Co1—C1	109.9 (3)	C13—C14—H14	119.7
C8—Co1—C1	167.3 (4)	C15—C14—H14	119.7
C9—Co1—C4	104.8 (3)	C14—C15—C16	119.3 (7)
C10—Co1—C4	125.3 (4)	C14—C15—H15	120.3
C2—Co1—C4	68.8 (3)	C16—C15—H15	120.3
C5—Co1—C4	40.5 (3)	C11—C16—C15	120.5 (6)
C7—Co1—C4	151.8 (4)	C11—C16—H16	119.7
C6—Co1—C4	163.6 (4)	C15—C16—H16	119.7
C8—Co1—C4	116.7 (4)	C18—C17—C22	120.7 (5)
C1—Co1—C4	68.9 (2)	C18—C17—P1	120.2 (4)
C9—Co1—C3	125.6 (4)	C22—C17—P1	119.1 (4)
C10—Co1—C3	162.9 (4)	C17—C18—C19	119.0 (6)
C2—Co1—C3	40.5 (3)	C17—C18—H18	120.5
C5—Co1—C3	69.1 (3)	C19—C18—H18	120.5
C7—Co1—C3	118.7 (4)	C20—C19—C18	119.8 (7)
C6—Co1—C3	154.8 (4)	C20—C19—H19	120.1
C8—Co1—C3	106.9 (4)	C18—C19—H19	120.1
C1—Co1—C3	69.2 (2)	C19—C20—C21	121.3 (6)
C4—Co1—C3	41.3 (3)	C19—C20—H20	119.4
C5—C1—C2	106.7 (5)	C21—C20—H20	119.4
C5—C1—P1	128.9 (4)	C20—C21—C22	119.9 (7)
C2—C1—P1	124.3 (4)	C20—C21—H21	120.1
C5—C1—Co1	68.9 (3)	C22—C21—H21	120.1
C2—C1—Co1	68.7 (3)	C21—C22—C17	119.4 (6)
P1—C1—Co1	126.2 (3)	C21—C22—H22	120.3
C3—C2—C1	108.8 (6)	C17—C22—H22	120.3
C3—C2—Co1	70.5 (4)	C1—P1—C11	103.1 (2)
C1—C2—Co1	69.8 (3)	C1—P1—C17	106.6 (2)
C3—C2—H2	125.6	C11—P1—C17	105.6 (2)
C1—C2—H2	125.6	C1—P1—Au1	113.37 (18)
Co1—C2—H2	125.6	C11—P1—Au1	111.84 (17)
C2—C3—C4	107.6 (6)	C17—P1—Au1	115.32 (19)
C2—C3—Co1	69.0 (3)	F3ⁱ—P2—F3	179.8 (6)
C4—C3—Co1	69.2 (4)	F3ⁱ—P2—F1	90.7 (7)
C2—C3—H3	126.2	F3—P2—F1	89.3 (7)
C4—C3—H3	126.2	F3ⁱ—P2—F1ⁱ	89.3 (6)
Co1—C3—H3	126.2	F3—P2—F1ⁱ	90.7 (7)
C5—C4—C3	108.3 (6)	F1—P2—F1ⁱ	178.9 (6)
C5—C4—Co1	69.2 (4)	F3ⁱ—P2—F2	90.1 (3)
C3—C4—Co1	69.5 (4)	F3—P2—F2	90.1 (3)
C5—C4—H4	125.9	F1—P2—F2	90.5 (3)
C3—C4—H4	125.9	F1ⁱ—P2—F2	90.5 (3)
Co1—C4—H4	125.9	F3ⁱ—P2—F4	89.9 (3)
C4—C5—C1	108.7 (6)	F3—P2—F4	89.9 (3)
C4—C5—Co1	70.3 (4)	F1—P2—F4	89.5 (3)
C1—C5—Co1	69.8 (3)	F1ⁱ—P2—F4	89.5 (3)
C4—C5—H5	125.7	F2—P2—F4	180.000 (1)
C1—C5—H5	125.7	F6—P3—F6ⁱⁱ	174.2 (8)
Co1—C5—H5	125.7	F6—P3—F5ⁱⁱ	94.0 (7)
C10—C6—C7	107.5 (8)	F6ⁱⁱ—P3—F5ⁱⁱ	85.7 (7)
C10—C6—Co1	69.2 (5)	F6—P3—F5	85.7 (7)
C7—C6—Co1	69.3 (5)	F6ⁱⁱ—P3—F5	94.0 (7)
C10—C6—H6	126.2	F5ⁱⁱ—P3—F5	173.1 (9)
C7—C6—H6	126.2	F6—P3—F8	92.9 (4)
Co1—C6—H6	126.2	F6ⁱⁱ—P3—F8	92.9 (4)
C8—C7—C6	106.4 (8)	F5ⁱⁱ—P3—F8	93.4 (4)
C8—C7—Co1	69.7 (5)	F5—P3—F8	93.4 (4)
C6—C7—Co1	69.4 (4)	F6—P3—F7	87.1 (4)
C8—C7—H7	126.8	F6ⁱⁱ—P3—F7	87.1 (4)
C6—C7—H7	126.8	F5ⁱⁱ—P3—F7	86.6 (4)
Co1—C7—H7	126.8	F5—P3—F7	86.6 (4)
C7—C8—C9	107.9 (8)	F8—P3—F7	180.000 (2)

C9—Co1—C1—C5	−45.1 (8)	C8—Co1—C6—C7	38.5 (5)
C10—Co1—C1—C5	−82.2 (5)	C1—Co1—C6—C7	−128.0 (5)
C2—Co1—C1—C5	118.8 (5)	C4—Co1—C6—C7	149.4 (9)
C7—Co1—C1—C5	−167.7 (5)	C3—Co1—C6—C7	−44.8 (9)
C6—Co1—C1—C5	−125.2 (4)	C10—C6—C7—C8	−1.3 (8)
C8—Co1—C1—C5	155.8 (15)	Co1—C6—C7—C8	−60.2 (5)
C4—Co1—C1—C5	37.3 (4)	C10—C6—C7—Co1	58.9 (5)
C3—Co1—C1—C5	81.6 (4)	C9—Co1—C7—C8	37.6 (6)
C9—Co1—C1—C2	−163.9 (6)	C10—Co1—C7—C8	80.3 (6)
C10—Co1—C1—C2	159.0 (4)	C2—Co1—C7—C8	−126.0 (5)
C5—Co1—C1—C2	−118.8 (5)	C5—Co1—C7—C8	151.9 (13)
C7—Co1—C1—C2	73.6 (5)	C6—Co1—C7—C8	117.5 (7)
C6—Co1—C1—C2	116.0 (4)	C1—Co1—C7—C8	−168.4 (5)
C8—Co1—C1—C2	37.0 (16)	C4—Co1—C7—C8	−44.8 (9)
C4—Co1—C1—C2	−81.5 (4)	C3—Co1—C7—C8	−82.5 (6)
C3—Co1—C1—C2	−37.1 (4)	C9—Co1—C7—C6	−79.9 (5)
C9—Co1—C1—P1	78.4 (8)	C10—Co1—C7—C6	−37.1 (5)
C10—Co1—C1—P1	41.3 (5)	C2—Co1—C7—C6	116.6 (5)
C2—Co1—C1—P1	−117.7 (5)	C5—Co1—C7—C6	34.4 (16)
C5—Co1—C1—P1	123.6 (5)	C8—Co1—C7—C6	−117.5 (7)
C7—Co1—C1—P1	−44.1 (6)	C1—Co1—C7—C6	74.1 (6)
C6—Co1—C1—P1	−1.7 (5)	C4—Co1—C7—C6	−162.3 (6)
C8—Co1—C1—P1	−80.7 (16)	C3—Co1—C7—C6	160.0 (5)
C4—Co1—C1—P1	160.8 (4)	C6—C7—C8—C9	2.1 (9)
C3—Co1—C1—P1	−154.8 (4)	Co1—C7—C8—C9	−57.8 (5)
C5—C1—C2—C3	1.2 (7)	C6—C7—C8—Co1	59.9 (5)
P1—C1—C2—C3	180.0 (4)	C9—Co1—C8—C7	−120.0 (8)
Co1—C1—C2—C3	59.9 (4)	C10—Co1—C8—C7	−82.4 (6)
C5—C1—C2—Co1	−58.7 (4)	C2—Co1—C8—C7	75.1 (6)
P1—C1—C2—Co1	120.1 (4)	C5—Co1—C8—C7	−168.0 (6)
C9—Co1—C2—C3	30.1 (13)	C6—Co1—C8—C7	−39.1 (5)
C10—Co1—C2—C3	−167.9 (7)	C1—Co1—C8—C7	44.7 (18)
C5—Co1—C2—C3	−81.6 (5)	C4—Co1—C8—C7	158.1 (5)
C7—Co1—C2—C3	111.9 (5)	C3—Co1—C8—C7	114.7 (6)
C6—Co1—C2—C3	155.9 (5)	C10—Co1—C8—C9	37.6 (6)
C8—Co1—C2—C3	70.0 (6)	C2—Co1—C8—C9	−164.9 (5)
C1—Co1—C2—C3	−119.7 (6)	C5—Co1—C8—C9	−48.0 (10)
C4—Co1—C2—C3	−38.0 (4)	C7—Co1—C8—C9	120.0 (8)
C9—Co1—C2—C1	149.8 (11)	C6—Co1—C8—C9	80.9 (6)
C10—Co1—C2—C1	−48.2 (9)	C1—Co1—C8—C9	164.7 (13)
C5—Co1—C2—C1	38.1 (3)	C4—Co1—C8—C9	−81.9 (6)
C7—Co1—C2—C1	−128.4 (4)	C3—Co1—C8—C9	−125.3 (6)
C6—Co1—C2—C1	−84.4 (5)	C7—C8—C9—C10	−2.2 (9)
C8—Co1—C2—C1	−170.3 (5)	Co1—C8—C9—C10	−60.7 (5)
C4—Co1—C2—C1	81.6 (4)	C7—C8—C9—Co1	58.5 (5)
C3—Co1—C2—C1	119.7 (6)	C2—Co1—C9—C10	168.4 (10)
C1—C2—C3—C4	−0.8 (7)	C5—Co1—C9—C10	−86.3 (6)
Co1—C2—C3—C4	58.7 (5)	C7—Co1—C9—C10	80.9 (6)
C1—C2—C3—Co1	−59.4 (4)	C6—Co1—C9—C10	36.4 (5)
C9—Co1—C3—C2	−170.5 (4)	C8—Co1—C9—C10	118.0 (8)
C10—Co1—C3—C2	162.6 (10)	C1—Co1—C9—C10	−55.1 (9)
C5—Co1—C3—C2	82.4 (4)	C4—Co1—C9—C10	−128.1 (5)
C7—Co1—C3—C2	−86.6 (5)	C3—Co1—C9—C10	−168.0 (5)
C6—Co1—C3—C2	−54.5 (8)	C10—Co1—C9—C8	−118.0 (8)
C8—Co1—C3—C2	−129.1 (5)	C2—Co1—C9—C8	50.3 (14)
C1—Co1—C3—C2	38.1 (4)	C5—Co1—C9—C8	155.7 (6)
C4—Co1—C3—C2	119.4 (6)	C7—Co1—C9—C8	−37.2 (6)
C9—Co1—C3—C4	70.1 (5)	C6—Co1—C9—C8	−81.7 (6)
C10—Co1—C3—C4	43.1 (12)	C1—Co1—C9—C8	−173.1 (6)
C2—Co1—C3—C4	−119.4 (6)	C4—Co1—C9—C8	113.8 (6)
C5—Co1—C3—C4	−37.1 (4)	C3—Co1—C9—C8	73.9 (7)
C7—Co1—C3—C4	154.0 (4)	C8—C9—C10—C6	1.4 (9)
C6—Co1—C3—C4	−174.0 (6)	Co1—C9—C10—C6	−59.4 (5)
C8—Co1—C3—C4	111.5 (5)	C8—C9—C10—Co1	60.8 (5)
C1—Co1—C3—C4	−81.3 (4)	C7—C6—C10—C9	−0.1 (9)
C2—C3—C4—C5	0.0 (8)	Co1—C6—C10—C9	58.9 (6)
Co1—C3—C4—C5	58.5 (5)	C7—C6—C10—Co1	−58.9 (5)
C2—C3—C4—Co1	−58.5 (5)	C2—Co1—C10—C9	−172.6 (6)
C9—Co1—C4—C5	112.2 (5)	C5—Co1—C10—C9	109.6 (5)
C10—Co1—C4—C5	74.2 (5)	C7—Co1—C10—C9	−83.0 (6)
C2—Co1—C4—C5	−82.6 (4)	C6—Co1—C10—C9	−121.3 (7)
C7—Co1—C4—C5	−174.4 (6)	C8—Co1—C10—C9	−38.9 (6)
C6—Co1—C4—C5	50.9 (12)	C1—Co1—C10—C9	152.7 (5)
C8—Co1—C4—C5	154.6 (5)	C4—Co1—C10—C9	68.7 (6)
C1—Co1—C4—C5	−37.9 (4)	C3—Co1—C10—C9	35.2 (13)
C3—Co1—C4—C5	−120.0 (6)	C9—Co1—C10—C6	121.3 (7)
C9—Co1—C4—C3	−127.8 (5)	C2—Co1—C10—C6	−51.3 (9)
C10—Co1—C4—C3	−165.8 (4)	C5—Co1—C10—C6	−129.1 (5)
C2—Co1—C4—C3	37.4 (4)	C7—Co1—C10—C6	38.3 (5)
C5—Co1—C4—C3	120.0 (6)	C8—Co1—C10—C6	82.4 (6)
C7—Co1—C4—C3	−54.4 (8)	C1—Co1—C10—C6	−86.0 (5)
C6—Co1—C4—C3	170.9 (9)	C4—Co1—C10—C6	−170.0 (4)
C8—Co1—C4—C3	−85.4 (5)	C3—Co1—C10—C6	156.5 (10)
C1—Co1—C4—C3	82.1 (4)	C16—C11—C12—C13	0.3 (9)
C3—C4—C5—C1	0.8 (8)	P1—C11—C12—C13	177.0 (6)
Co1—C4—C5—C1	59.5 (4)	C11—C12—C13—C14	−0.9 (11)
C3—C4—C5—Co1	−58.7 (5)	C12—C13—C14—C15	0.5 (13)
C2—C1—C5—C4	−1.2 (7)	C13—C14—C15—C16	0.4 (12)
P1—C1—C5—C4	−179.9 (5)	C12—C11—C16—C15	0.6 (9)
Co1—C1—C5—C4	−59.7 (5)	P1—C11—C16—C15	−175.9 (5)
C2—C1—C5—Co1	58.5 (4)	C14—C15—C16—C11	−1.0 (11)
P1—C1—C5—Co1	−120.2 (5)	C22—C17—C18—C19	−1.7 (9)
C9—Co1—C5—C4	−82.8 (5)	P1—C17—C18—C19	−179.4 (5)
C10—Co1—C5—C4	−124.7 (5)	C17—C18—C19—C20	2.1 (10)
C2—Co1—C5—C4	81.2 (4)	C18—C19—C20—C21	−2.4 (10)
C7—Co1—C5—C4	168.0 (13)	C19—C20—C21—C22	2.1 (10)
C6—Co1—C5—C4	−163.9 (5)	C20—C21—C22—C17	−1.7 (9)
C8—Co1—C5—C4	−50.0 (9)	C18—C17—C22—C21	1.5 (8)
C1—Co1—C5—C4	119.6 (6)	P1—C17—C22—C21	179.2 (5)
C3—Co1—C5—C4	37.7 (4)	C5—C1—P1—C11	−89.4 (5)
C9—Co1—C5—C1	157.5 (4)	C2—C1—P1—C11	92.2 (5)
C10—Co1—C5—C1	115.7 (4)	Co1—C1—P1—C11	179.5 (3)
C2—Co1—C5—C1	−38.4 (3)	C5—C1—P1—C17	21.5 (6)
C7—Co1—C5—C1	48.3 (15)	C2—C1—P1—C17	−156.9 (5)
C6—Co1—C5—C1	76.5 (5)	Co1—C1—P1—C17	−69.6 (4)
C8—Co1—C5—C1	−169.6 (7)	C5—C1—P1—Au1	149.5 (5)
C4—Co1—C5—C1	−119.6 (6)	C2—C1—P1—Au1	−29.0 (5)
C3—Co1—C5—C1	−81.9 (4)	Co1—C1—P1—Au1	58.4 (4)
C9—Co1—C6—C10	−36.1 (5)	C16—C11—P1—C1	−2.2 (6)
C2—Co1—C6—C10	157.4 (5)	C12—C11—P1—C1	−178.8 (4)
C5—Co1—C6—C10	69.9 (6)	C16—C11—P1—C17	−113.9 (5)
C7—Co1—C6—C10	−119.2 (7)	C12—C11—P1—C17	69.5 (5)
C8—Co1—C6—C10	−80.6 (6)	C16—C11—P1—Au1	120.0 (5)
C1—Co1—C6—C10	112.8 (5)	C12—C11—P1—Au1	−56.6 (5)
C4—Co1—C6—C10	30.2 (12)	C18—C17—P1—C1	−71.4 (5)
C3—Co1—C6—C10	−164.0 (6)	C22—C17—P1—C1	110.9 (4)
C9—Co1—C6—C7	83.1 (5)	C18—C17—P1—C11	37.8 (5)
C10—Co1—C6—C7	119.2 (7)	C22—C17—P1—C11	−139.9 (4)
C2—Co1—C6—C7	−83.4 (5)	C18—C17—P1—Au1	161.8 (4)
C5—Co1—C6—C7	−171.0 (5)	C22—C17—P1—Au1	−15.9 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F5ⁱⁱⁱ	0.98	2.56	3.249 (11)	128
C8—H8···F4ⁱⁱⁱ	0.98	2.41	3.090 (10)	126
C10—H10···F8ⁱⁱⁱ	0.98	2.53	3.185 (12)	125

Symmetry code: (iii) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[AuCo(C₅H₅)(C₁₇H₁₄P)Cl]PF₆
M_r	750.66
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	292
a, b, c (Å)	11.5565 (14), 14.8537 (14), 27.983 (3)
β (°)	97.577 (2)
V (Å³)	4761.6 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	7.15
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	24437, 4680, 4190
R_int	0.183
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.125, 1.06
No. of reflections	4680
No. of parameters	301
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	3.36, −1.59

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F5ⁱ	0.98	2.56	3.249 (11)	128
C8—H8···F4ⁱ	0.98	2.41	3.090 (10)	126
C10—H10···F8ⁱ	0.98	2.53	3.185 (12)	125

Symmetry code: (i) x+1/2, y+1/2, z.

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 21002086) and the Application Foundation of Yunnan Provice (grant No. 2010ZC071).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Y., Wu, X.-H., Yu, G.-A., Jin, S., Meng, X.-G. & Liu, S.-H. (2009). Transition Met. Chem. 34, 103–108. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar