(η⁵-Cyclo­penta­dien­yl)[η⁵-1-(diphenyl­phosphino)cyclo­penta­dien­yl]cobalt(III) hexa­fluoro­phosphate

In the title cobaltocenium compound, [Co(C₅H₅)(C₁₇H₁₁₄P)]PF₆, the Co^III atom carries both cyclo­penta­dienenyl and diphenyl­phosphinocyclo­penta­dienyl ligands inclined to each other at 3.2 (1)°. The disordered PF₆⁻ anion links with the cobaltocenium cation via weak C—H...F hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.046
• wR factor = 0.129
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        Co1

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P2
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      36.00 Perc.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Cobaltocene derivatives have been applied as catalysts in cross-coupling reactions (Matthews or Mathews et al., 2000). As part of our investigations of new catalysts, we have focused our attention on cobaltocenium compounds and report here the structure of the title compound, (I) (Fig. 1 and Table 1).

In (I), the Co^III atom carries both cyclopentadienenyl and diphenylphosphinocyclopentadienyl ligands inclined to each other at 3.2 (1)°. The Co1···Cg1 and Co1···Cg2 distances are 1.643 (2) and 1.637 (8) Å, respectively, and the Cg1···Co1···Cg2 angle is 175.9 (8)° (Cg1 and Cg2 are the centroids of the five-membered cyclopentadienyl and diphenylphosphinocyclopentadienyl rings, respectively). These rings are approximately eclipsed. The disordered PF₆⁻ anion links to the cobaltocenium cation via weak C—H···F hydrogen bonds (Fig. 2 and Table 2).

S2. Experimental

The title compound was prepared according to the method of Brasse et al. (2000). Single crystals were obtained by show diffusion of diethyl ether into a solution of the compound in acetone.

S3. Refinement

At an early stage in the refinement, disorder was apparent in four of the F atoms of the hexafluorophosphate anion. The disordered F atoms were assigned the same isotropic displacement parameters, and bond distances in the minor disorder component were constrained using DFIX and PART in SHELXL (Sheldrick, 1997). The occupation factors of the two components converged at 0.799 (6) and 0.201 (6). All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with aromatic C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I), shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).
	Fig. 2. The unit-cell packing of (I), showing the formation of chains along [010]. Hydrogen bonds are shown as dashed lines and, for the sake of clarity, H atoms not involved in hydrogen bonding have been omitted.

(η⁵-Cyclopentadienyl)[η⁵-1- (diphenylphosphino)cyclopentadienyl]cobalt(III) hexafluorophosphate

Crystal data

[Co(C5H5)(C17H14P)]PF6	F(000) = 2096
Mr = 518.24	Dx = 1.557 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4616 reflections
a = 36.813 (3) Å	θ = 2.2–26.0°
b = 10.2263 (8) Å	µ = 0.98 mm^−1
c = 11.9059 (9) Å	T = 292 K
β = 99.469 (1)°	Block, yellow
V = 4421.0 (6) Å^3	0.30 × 0.30 × 0.30 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	4335 independent reflections
Radiation source: fine-focus sealed tube	3275 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ϕ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −45→39
Tmin = 0.758, Tmax = 0.758	k = −12→12
14389 measured reflections	l = −11→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.074P)^2] where P = (Fo^2 + 2Fc^2)/3
4335 reflections	(Δ/σ)max < 0.001
297 parameters	Δρmax = 0.40 e Å^−3
8 restraints	Δρmin = −0.27 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.574497 (11)	0.73432 (4)	0.56912 (3)	0.05056 (16)
C1	0.5811 (2)	0.8233 (5)	0.7214 (3)	0.1031 (16)
H1	0.5940	0.9061	0.7408	0.124*
C2	0.54694 (19)	0.8104 (6)	0.6854 (4)	0.1052 (16)
H2	0.5299	0.8843	0.6701	0.126*
C3	0.53731 (14)	0.6919 (7)	0.6684 (4)	0.1077 (16)
H3	0.5121	0.6622	0.6410	0.129*
C4	0.5668 (2)	0.6129 (4)	0.6948 (4)	0.1112 (19)
H4	0.5670	0.5171	0.6929	0.133*
C5	0.59735 (12)	0.6967 (8)	0.7305 (3)	0.116 (2)
H5	0.6229	0.6727	0.7603	0.140*
C6	0.59172 (9)	0.8557 (3)	0.4538 (2)	0.0593 (7)
H6	0.6010	0.9449	0.4690	0.071*
C7	0.55452 (9)	0.8207 (4)	0.4190 (3)	0.0704 (9)
H7	0.5336	0.8812	0.4050	0.084*
C8	0.55266 (9)	0.6832 (4)	0.4077 (3)	0.0681 (8)
H8	0.5303	0.6315	0.3847	0.082*
C9	0.58881 (7)	0.6334 (3)	0.4357 (2)	0.0536 (7)
H9	0.5957	0.5407	0.4365	0.064*
C10	0.61356 (8)	0.7396 (2)	0.4639 (2)	0.0469 (6)
C11	0.67390 (7)	0.5686 (2)	0.4723 (2)	0.0492 (6)
C12	0.66697 (8)	0.4687 (3)	0.5436 (3)	0.0661 (8)
H12	0.6564	0.4876	0.6075	0.079*
C13	0.67563 (10)	0.3407 (3)	0.5212 (4)	0.0820 (11)
H13	0.6702	0.2735	0.5684	0.098*
C14	0.69213 (11)	0.3137 (3)	0.4298 (4)	0.0873 (12)
H14	0.6983	0.2278	0.4154	0.105*
C15	0.69975 (10)	0.4115 (3)	0.3588 (3)	0.0806 (10)
H15	0.7112	0.3921	0.2968	0.097*
C16	0.69048 (8)	0.5387 (3)	0.3791 (3)	0.0615 (8)
H16	0.6954	0.6048	0.3300	0.074*
C17	0.68002 (7)	0.8382 (2)	0.4083 (2)	0.0454 (6)
C18	0.71507 (7)	0.8906 (3)	0.4393 (3)	0.0553 (7)
H18	0.7286	0.8709	0.5103	0.066*
C19	0.72991 (8)	0.9709 (3)	0.3666 (3)	0.0696 (9)
H19	0.7535	1.0047	0.3880	0.084*
C20	0.70995 (9)	1.0015 (3)	0.2624 (3)	0.0702 (9)
H20	0.7200	1.0566	0.2135	0.084*
C21	0.67533 (9)	0.9514 (3)	0.2296 (3)	0.0657 (8)
H21	0.6620	0.9722	0.1586	0.079*
C22	0.66034 (8)	0.8699 (3)	0.3026 (2)	0.0579 (7)
H22	0.6368	0.8360	0.2804	0.069*
F1	0.46340 (7)	0.8599 (2)	0.5166 (2)	0.1281 (10)
F3	0.40790 (6)	0.6784 (2)	0.3582 (2)	0.1051 (8)
F2	0.46675 (8)	0.7054 (4)	0.3794 (4)	0.1273 (18)	0.799 (6)
F6	0.44228 (17)	0.6614 (3)	0.5326 (3)	0.1349 (19)	0.799 (6)
F4	0.40419 (9)	0.8300 (4)	0.4950 (4)	0.1260 (17)	0.799 (6)
F5	0.42715 (12)	0.8769 (3)	0.3443 (3)	0.1285 (17)	0.799 (6)
P1	0.66317 (2)	0.73511 (7)	0.51418 (6)	0.0487 (2)
P2	0.43623 (2)	0.76799 (7)	0.43801 (7)	0.0568 (2)
F2'	0.4588 (4)	0.8384 (13)	0.3552 (10)	0.100 (5)*	0.201 (6)
F4'	0.4139 (4)	0.6996 (13)	0.5184 (10)	0.094 (4)*	0.201 (6)
F6'	0.4655 (3)	0.6569 (9)	0.4644 (12)	0.076 (3)*	0.201 (6)
F5'	0.4063 (3)	0.8747 (9)	0.4184 (10)	0.068 (3)*	0.201 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0527 (3)	0.0568 (3)	0.0452 (3)	0.00436 (16)	0.01689 (19)	−0.00092 (16)
C1	0.153 (5)	0.110 (4)	0.053 (2)	−0.045 (3)	0.036 (3)	−0.025 (2)
C2	0.132 (5)	0.121 (4)	0.077 (3)	0.048 (3)	0.060 (3)	0.009 (3)
C3	0.098 (3)	0.169 (5)	0.063 (3)	−0.049 (4)	0.034 (2)	0.002 (3)
C4	0.227 (7)	0.058 (2)	0.059 (3)	0.011 (3)	0.054 (4)	0.0127 (18)
C5	0.073 (3)	0.245 (6)	0.0340 (19)	0.065 (4)	0.0158 (19)	0.030 (3)
C6	0.070 (2)	0.0584 (16)	0.0540 (18)	0.0111 (14)	0.0251 (15)	0.0102 (14)
C7	0.059 (2)	0.101 (2)	0.0531 (19)	0.0268 (18)	0.0173 (16)	0.0191 (17)
C8	0.0533 (18)	0.101 (2)	0.0511 (19)	0.0007 (17)	0.0108 (15)	−0.0115 (17)
C9	0.0504 (16)	0.0661 (16)	0.0458 (16)	0.0004 (13)	0.0128 (13)	−0.0116 (13)
C10	0.0501 (16)	0.0532 (14)	0.0398 (15)	0.0034 (11)	0.0148 (12)	−0.0013 (11)
C11	0.0396 (14)	0.0518 (14)	0.0552 (17)	−0.0003 (11)	0.0047 (12)	0.0034 (12)
C12	0.0594 (18)	0.0641 (18)	0.078 (2)	0.0034 (14)	0.0206 (16)	0.0135 (16)
C13	0.071 (2)	0.0612 (19)	0.114 (3)	0.0014 (17)	0.014 (2)	0.016 (2)
C14	0.083 (3)	0.0528 (18)	0.125 (4)	0.0071 (18)	0.014 (3)	−0.008 (2)
C15	0.082 (2)	0.073 (2)	0.091 (3)	0.0081 (18)	0.026 (2)	−0.016 (2)
C16	0.0647 (18)	0.0597 (17)	0.0624 (19)	0.0019 (14)	0.0175 (16)	−0.0039 (14)
C17	0.0483 (15)	0.0460 (13)	0.0420 (15)	0.0007 (11)	0.0077 (12)	−0.0039 (11)
C18	0.0468 (15)	0.0612 (16)	0.0568 (18)	−0.0017 (13)	0.0049 (13)	−0.0006 (14)
C19	0.0491 (17)	0.078 (2)	0.083 (3)	−0.0136 (15)	0.0123 (17)	0.0048 (17)
C20	0.070 (2)	0.0683 (18)	0.078 (2)	−0.0048 (16)	0.0271 (18)	0.0151 (17)
C21	0.069 (2)	0.0712 (19)	0.0559 (19)	−0.0004 (16)	0.0072 (16)	0.0160 (15)
C22	0.0521 (16)	0.0653 (17)	0.0541 (18)	−0.0057 (13)	0.0022 (14)	0.0012 (14)
F1	0.1131 (18)	0.0964 (15)	0.153 (2)	−0.0172 (14)	−0.0440 (17)	−0.0301 (16)
F3	0.0875 (15)	0.0799 (13)	0.135 (2)	0.0043 (11)	−0.0217 (14)	−0.0312 (14)
F2	0.0677 (19)	0.162 (4)	0.160 (4)	0.0091 (19)	0.044 (2)	−0.045 (3)
F6	0.215 (5)	0.091 (2)	0.090 (2)	−0.015 (3)	−0.001 (3)	0.0377 (17)
F4	0.114 (3)	0.117 (3)	0.162 (4)	−0.008 (2)	0.068 (3)	−0.052 (3)
F5	0.159 (4)	0.095 (2)	0.116 (3)	−0.020 (2)	−0.024 (3)	0.0532 (19)
P1	0.0495 (4)	0.0538 (4)	0.0428 (4)	−0.0024 (3)	0.0075 (3)	−0.0010 (3)
P2	0.0582 (5)	0.0543 (4)	0.0569 (5)	−0.0019 (3)	0.0062 (4)	0.0016 (3)

Geometric parameters (Å, º)

Co1—C3	1.998 (4)	C11—P1	1.836 (3)
Co1—C4	2.000 (4)	C12—C13	1.384 (4)
Co1—C2	2.003 (4)	C12—H12	0.9300
Co1—C5	2.004 (3)	C13—C14	1.359 (6)
Co1—C1	2.008 (4)	C13—H13	0.9300
Co1—C7	2.021 (3)	C14—C15	1.369 (5)
Co1—C8	2.026 (3)	C14—H14	0.9300
Co1—C6	2.028 (3)	C15—C16	1.375 (4)
Co1—C9	2.035 (3)	C15—H15	0.9300
Co1—C10	2.058 (3)	C16—H16	0.9300
C1—C2	1.267 (7)	C17—C22	1.383 (4)
C1—C5	1.423 (7)	C17—C18	1.390 (3)
C1—H1	0.9800	C17—P1	1.829 (3)
C2—C3	1.269 (7)	C18—C19	1.371 (4)
C2—H2	0.9800	C18—H18	0.9300
C3—C4	1.349 (7)	C19—C20	1.370 (4)
C3—H3	0.9800	C19—H19	0.9300
C4—C5	1.422 (7)	C20—C21	1.369 (4)
C4—H4	0.9800	C20—H20	0.9300
C5—H5	0.9800	C21—C22	1.383 (4)
C6—C7	1.410 (4)	C21—H21	0.9300
C6—C10	1.428 (4)	C22—H22	0.9300
C6—H6	0.9800	F1—P2	1.566 (2)
C7—C8	1.414 (5)	F3—P2	1.582 (2)
C7—H7	0.9800	F2—P2	1.554 (3)
C8—C9	1.413 (4)	F6—P2	1.557 (3)
C8—H8	0.9800	F4—P2	1.586 (3)
C9—C10	1.422 (4)	F5—P2	1.573 (3)
C9—H9	0.9800	P2—F4'	1.530 (8)
C10—P1	1.826 (3)	P2—F5'	1.541 (7)
C11—C12	1.379 (4)	P2—F6'	1.561 (7)
C11—C16	1.386 (4)	P2—F2'	1.565 (8)
C3—Co1—C4	39.45 (19)	C8—C9—C10	108.8 (3)
C3—Co1—C2	37.0 (2)	C8—C9—Co1	69.31 (17)
C4—Co1—C2	64.81 (19)	C10—C9—Co1	70.53 (16)
C3—Co1—C5	67.14 (19)	C8—C9—H9	125.6
C4—Co1—C5	41.6 (2)	C10—C9—H9	125.6
C2—Co1—C5	65.95 (19)	Co1—C9—H9	125.6
C3—Co1—C1	63.70 (19)	C9—C10—C6	106.6 (3)
C4—Co1—C1	67.46 (18)	C9—C10—P1	128.7 (2)
C2—Co1—C1	36.8 (2)	C6—C10—P1	124.5 (2)
C5—Co1—C1	41.5 (2)	C9—C10—Co1	68.82 (16)
C3—Co1—C7	115.7 (2)	C6—C10—Co1	68.45 (16)
C4—Co1—C7	149.0 (3)	P1—C10—Co1	124.12 (15)
C2—Co1—C7	106.82 (18)	C12—C11—C16	118.7 (3)
C5—Co1—C7	165.1 (3)	C12—C11—P1	116.7 (2)
C1—Co1—C7	125.0 (2)	C16—C11—P1	124.4 (2)
C3—Co1—C8	107.55 (17)	C11—C12—C13	120.6 (3)
C4—Co1—C8	117.8 (2)	C11—C12—H12	119.7
C2—Co1—C8	126.1 (2)	C13—C12—H12	119.7
C5—Co1—C8	154.0 (3)	C14—C13—C12	119.7 (4)
C1—Co1—C8	160.7 (2)	C14—C13—H13	120.2
C7—Co1—C8	40.89 (15)	C12—C13—H13	120.2
C3—Co1—C6	148.7 (2)	C13—C14—C15	120.6 (3)
C4—Co1—C6	170.0 (3)	C13—C14—H14	119.7
C2—Co1—C6	118.70 (19)	C15—C14—H14	119.7
C5—Co1—C6	129.6 (2)	C14—C15—C16	120.0 (3)
C1—Co1—C6	109.22 (16)	C14—C15—H15	120.0
C7—Co1—C6	40.76 (13)	C16—C15—H15	120.0
C8—Co1—C6	68.61 (14)	C15—C16—C11	120.3 (3)
C3—Co1—C9	130.0 (2)	C15—C16—H16	119.9
C4—Co1—C9	110.82 (15)	C11—C16—H16	119.9
C2—Co1—C9	164.1 (2)	C22—C17—C18	118.4 (3)
C5—Co1—C9	121.96 (18)	C22—C17—P1	125.2 (2)
C1—Co1—C9	157.9 (2)	C18—C17—P1	116.4 (2)
C7—Co1—C9	68.58 (13)	C19—C18—C17	120.8 (3)
C8—Co1—C9	40.71 (12)	C19—C18—H18	119.6
C6—Co1—C9	68.42 (13)	C17—C18—H18	119.6
C3—Co1—C10	169.0 (2)	C20—C19—C18	119.9 (3)
C4—Co1—C10	132.1 (2)	C20—C19—H19	120.1
C2—Co1—C10	153.5 (2)	C18—C19—H19	120.1
C5—Co1—C10	111.33 (14)	C21—C20—C19	120.6 (3)
C1—Co1—C10	123.05 (19)	C21—C20—H20	119.7
C7—Co1—C10	68.84 (12)	C19—C20—H20	119.7
C8—Co1—C10	68.71 (12)	C20—C21—C22	119.7 (3)
C6—Co1—C10	40.91 (10)	C20—C21—H21	120.2
C9—Co1—C10	40.65 (10)	C22—C21—H21	120.2
C2—C1—C5	108.2 (5)	C17—C22—C21	120.6 (3)
C2—C1—Co1	71.4 (3)	C17—C22—H22	119.7
C5—C1—Co1	69.1 (2)	C21—C22—H22	119.7
C2—C1—H1	125.9	C10—P1—C17	101.17 (12)
C5—C1—H1	125.9	C10—P1—C11	100.51 (11)
Co1—C1—H1	125.9	C17—P1—C11	103.59 (12)
C1—C2—C3	112.9 (5)	F4'—P2—F5'	88.5 (7)
C1—C2—Co1	71.8 (3)	F4'—P2—F2	126.5 (6)
C3—C2—Co1	71.3 (3)	F5'—P2—F2	140.8 (5)
C1—C2—H2	123.5	F5'—P2—F6	128.3 (5)
C3—C2—H2	123.5	F2—P2—F6	90.5 (2)
Co1—C2—H2	123.5	F4'—P2—F6'	88.0 (7)
C2—C3—C4	110.0 (5)	F5'—P2—F6'	176.4 (7)
C2—C3—Co1	71.7 (3)	F6—P2—F6'	48.1 (5)
C4—C3—Co1	70.3 (3)	F4'—P2—F2'	179.5 (8)
C2—C3—H3	125.0	F5'—P2—F2'	91.1 (7)
C4—C3—H3	125.0	F2—P2—F2'	53.8 (5)
Co1—C3—H3	125.0	F6—P2—F2'	138.6 (6)
C3—C4—C5	106.0 (4)	F6'—P2—F2'	92.4 (7)
C3—C4—Co1	70.2 (2)	F4'—P2—F1	104.9 (5)
C5—C4—Co1	69.4 (2)	F5'—P2—F1	92.0 (4)
C3—C4—H4	127.0	F2—P2—F1	94.47 (17)
C5—C4—H4	127.0	F6—P2—F1	89.22 (19)
Co1—C4—H4	127.0	F6'—P2—F1	88.0 (4)
C4—C5—C1	102.9 (4)	F2'—P2—F1	75.4 (5)
C4—C5—Co1	69.0 (2)	F4'—P2—F5	134.0 (6)
C1—C5—Co1	69.4 (2)	F5'—P2—F5	47.8 (4)
C4—C5—H5	128.4	F2—P2—F5	93.3 (3)
C1—C5—H5	128.4	F6—P2—F5	175.8 (3)
Co1—C5—H5	128.4	F6'—P2—F5	135.8 (6)
C7—C6—C10	108.7 (3)	F2'—P2—F5	45.6 (5)
C7—C6—Co1	69.34 (17)	F1—P2—F5	92.25 (16)
C10—C6—Co1	70.64 (16)	F4'—P2—F3	75.0 (5)
C7—C6—H6	125.7	F5'—P2—F3	86.3 (4)
C10—C6—H6	125.7	F2—P2—F3	86.90 (16)
Co1—C6—H6	125.7	F6—P2—F3	91.78 (19)
C6—C7—C8	108.0 (3)	F6'—P2—F3	93.7 (4)
C6—C7—Co1	69.91 (17)	F2'—P2—F3	104.7 (5)
C8—C7—Co1	69.75 (17)	F1—P2—F3	178.30 (13)
C6—C7—H7	126.0	F5—P2—F3	86.67 (16)
C8—C7—H7	126.0	F4'—P2—F4	53.2 (6)
Co1—C7—H7	126.0	F2—P2—F4	178.3 (2)
C9—C8—C7	107.9 (3)	F6—P2—F4	89.9 (3)
C9—C8—Co1	69.99 (17)	F6'—P2—F4	137.8 (6)
C7—C8—Co1	69.36 (17)	F2'—P2—F4	126.5 (6)
C9—C8—H8	126.0	F1—P2—F4	87.20 (17)
C7—C8—H8	126.0	F5—P2—F4	86.2 (2)
Co1—C8—H8	126.0	F3—P2—F4	91.43 (16)
C3—Co1—C1—C2	−34.3 (4)	C8—Co1—C7—C6	−119.1 (3)
C4—Co1—C1—C2	−77.6 (4)	C9—Co1—C7—C6	−81.38 (19)
C5—Co1—C1—C2	−118.8 (5)	C10—Co1—C7—C6	−37.61 (17)
C7—Co1—C1—C2	69.8 (4)	C3—Co1—C7—C8	−87.5 (3)
C8—Co1—C1—C2	32.5 (7)	C4—Co1—C7—C8	−57.3 (4)
C6—Co1—C1—C2	112.5 (3)	C2—Co1—C7—C8	−126.2 (3)
C9—Co1—C1—C2	−167.7 (4)	C5—Co1—C7—C8	175.1 (5)
C10—Co1—C1—C2	155.8 (3)	C1—Co1—C7—C8	−162.2 (3)
C3—Co1—C1—C5	84.5 (3)	C6—Co1—C7—C8	119.1 (3)
C4—Co1—C1—C5	41.2 (3)	C9—Co1—C7—C8	37.73 (17)
C2—Co1—C1—C5	118.8 (5)	C10—Co1—C7—C8	81.51 (18)
C7—Co1—C1—C5	−171.4 (3)	C6—C7—C8—C9	0.0 (3)
C8—Co1—C1—C5	151.3 (5)	Co1—C7—C8—C9	−59.6 (2)
C6—Co1—C1—C5	−128.7 (3)	C6—C7—C8—Co1	59.6 (2)
C9—Co1—C1—C5	−48.9 (5)	C3—Co1—C8—C9	−131.7 (3)
C10—Co1—C1—C5	−85.4 (3)	C4—Co1—C8—C9	−90.2 (3)
C5—C1—C2—C3	0.1 (5)	C2—Co1—C8—C9	−168.0 (3)
Co1—C1—C2—C3	59.6 (3)	C5—Co1—C8—C9	−58.0 (4)
C5—C1—C2—Co1	−59.5 (3)	C1—Co1—C8—C9	168.5 (4)
C3—Co1—C2—C1	123.0 (5)	C7—Co1—C8—C9	119.1 (3)
C4—Co1—C2—C1	85.5 (4)	C6—Co1—C8—C9	81.4 (2)
C5—Co1—C2—C1	39.5 (4)	C10—Co1—C8—C9	37.28 (17)
C7—Co1—C2—C1	−126.5 (4)	C3—Co1—C8—C7	109.2 (3)
C8—Co1—C2—C1	−167.3 (3)	C4—Co1—C8—C7	150.7 (3)
C6—Co1—C2—C1	−84.0 (4)	C2—Co1—C8—C7	72.9 (3)
C9—Co1—C2—C1	162.9 (5)	C5—Co1—C8—C7	−177.1 (3)
C10—Co1—C2—C1	−50.3 (5)	C1—Co1—C8—C7	49.4 (5)
C4—Co1—C2—C3	−37.5 (3)	C6—Co1—C8—C7	−37.78 (17)
C5—Co1—C2—C3	−83.4 (4)	C9—Co1—C8—C7	−119.1 (3)
C1—Co1—C2—C3	−123.0 (5)	C10—Co1—C8—C7	−81.85 (18)
C7—Co1—C2—C3	110.5 (4)	C7—C8—C9—C10	−0.4 (3)
C8—Co1—C2—C3	69.7 (4)	Co1—C8—C9—C10	−59.7 (2)
C6—Co1—C2—C3	153.1 (3)	C7—C8—C9—Co1	59.2 (2)
C9—Co1—C2—C3	39.9 (8)	C3—Co1—C9—C8	68.3 (3)
C10—Co1—C2—C3	−173.3 (3)	C4—Co1—C9—C8	108.9 (3)
C1—C2—C3—C4	0.3 (6)	C2—Co1—C9—C8	38.0 (7)
Co1—C2—C3—C4	60.2 (3)	C5—Co1—C9—C8	154.0 (3)
C1—C2—C3—Co1	−59.9 (4)	C1—Co1—C9—C8	−170.0 (4)
C4—Co1—C3—C2	120.0 (5)	C7—Co1—C9—C8	−37.9 (2)
C5—Co1—C3—C2	79.9 (4)	C6—Co1—C9—C8	−81.8 (2)
C1—Co1—C3—C2	34.1 (3)	C10—Co1—C9—C8	−120.0 (3)
C7—Co1—C3—C2	−84.0 (4)	C3—Co1—C9—C10	−171.8 (3)
C8—Co1—C3—C2	−127.3 (4)	C4—Co1—C9—C10	−131.2 (3)
C6—Co1—C3—C2	−49.8 (5)	C2—Co1—C9—C10	157.9 (6)
C9—Co1—C3—C2	−166.8 (3)	C5—Co1—C9—C10	−86.1 (3)
C10—Co1—C3—C2	164.2 (7)	C1—Co1—C9—C10	−50.0 (5)
C2—Co1—C3—C4	−120.0 (5)	C7—Co1—C9—C10	82.06 (19)
C5—Co1—C3—C4	−40.1 (3)	C8—Co1—C9—C10	120.0 (3)
C1—Co1—C3—C4	−85.9 (3)	C6—Co1—C9—C10	38.10 (17)
C7—Co1—C3—C4	156.0 (3)	C8—C9—C10—C6	0.7 (3)
C8—Co1—C3—C4	112.7 (3)	Co1—C9—C10—C6	−58.2 (2)
C6—Co1—C3—C4	−169.8 (3)	C8—C9—C10—P1	176.3 (2)
C9—Co1—C3—C4	73.2 (4)	Co1—C9—C10—P1	117.4 (2)
C10—Co1—C3—C4	44.2 (10)	C8—C9—C10—Co1	58.9 (2)
C2—C3—C4—C5	−0.6 (5)	C7—C6—C10—C9	−0.6 (3)
Co1—C3—C4—C5	60.5 (3)	Co1—C6—C10—C9	58.5 (2)
C2—C3—C4—Co1	−61.1 (3)	C7—C6—C10—P1	−176.5 (2)
C2—Co1—C4—C3	35.2 (3)	Co1—C6—C10—P1	−117.4 (2)
C5—Co1—C4—C3	116.6 (4)	C7—C6—C10—Co1	−59.1 (2)
C1—Co1—C4—C3	75.5 (3)	C3—Co1—C10—C9	34.8 (9)
C7—Co1—C4—C3	−45.5 (4)	C4—Co1—C10—C9	71.5 (3)
C8—Co1—C4—C3	−84.0 (3)	C2—Co1—C10—C9	−166.7 (4)
C9—Co1—C4—C3	−128.3 (3)	C5—Co1—C10—C9	114.7 (3)
C10—Co1—C4—C3	−169.6 (3)	C1—Co1—C10—C9	159.9 (3)
C3—Co1—C4—C5	−116.6 (4)	C7—Co1—C10—C9	−81.3 (2)
C2—Co1—C4—C5	−81.5 (3)	C8—Co1—C10—C9	−37.33 (18)
C1—Co1—C4—C5	−41.1 (3)	C6—Co1—C10—C9	−118.8 (3)
C7—Co1—C4—C5	−162.1 (3)	C3—Co1—C10—C6	153.6 (8)
C8—Co1—C4—C5	159.4 (3)	C4—Co1—C10—C6	−169.7 (3)
C9—Co1—C4—C5	115.1 (3)	C2—Co1—C10—C6	−47.9 (5)
C10—Co1—C4—C5	73.7 (3)	C5—Co1—C10—C6	−126.5 (3)
C3—C4—C5—C1	0.6 (4)	C1—Co1—C10—C6	−81.3 (3)
Co1—C4—C5—C1	61.6 (3)	C7—Co1—C10—C6	37.47 (19)
C3—C4—C5—Co1	−61.0 (3)	C8—Co1—C10—C6	81.5 (2)
C2—C1—C5—C4	−0.4 (5)	C9—Co1—C10—C6	118.8 (3)
Co1—C1—C5—C4	−61.4 (3)	C3—Co1—C10—P1	−88.4 (9)
C2—C1—C5—Co1	61.0 (3)	C4—Co1—C10—P1	−51.7 (3)
C3—Co1—C5—C4	38.1 (3)	C2—Co1—C10—P1	70.1 (4)
C2—Co1—C5—C4	78.5 (3)	C5—Co1—C10—P1	−8.6 (3)
C1—Co1—C5—C4	113.6 (4)	C1—Co1—C10—P1	36.7 (3)
C7—Co1—C5—C4	142.1 (6)	C7—Co1—C10—P1	155.4 (2)
C8—Co1—C5—C4	−45.2 (4)	C8—Co1—C10—P1	−160.57 (19)
C6—Co1—C5—C4	−173.3 (3)	C6—Co1—C10—P1	118.0 (2)
C9—Co1—C5—C4	−85.9 (3)	C9—Co1—C10—P1	−123.2 (2)
C10—Co1—C5—C4	−130.1 (3)	C16—C11—C12—C13	−1.5 (5)
C3—Co1—C5—C1	−75.6 (3)	P1—C11—C12—C13	−177.3 (3)
C4—Co1—C5—C1	−113.6 (4)	C11—C12—C13—C14	2.0 (5)
C2—Co1—C5—C1	−35.1 (3)	C12—C13—C14—C15	−1.0 (6)
C7—Co1—C5—C1	28.5 (7)	C13—C14—C15—C16	−0.5 (6)
C8—Co1—C5—C1	−158.8 (4)	C14—C15—C16—C11	1.0 (5)
C6—Co1—C5—C1	73.1 (3)	C12—C11—C16—C15	0.0 (5)
C9—Co1—C5—C1	160.5 (3)	P1—C11—C16—C15	175.5 (2)
C10—Co1—C5—C1	116.2 (3)	C22—C17—C18—C19	−0.5 (4)
C3—Co1—C6—C7	−50.9 (4)	P1—C17—C18—C19	−178.9 (2)
C2—Co1—C6—C7	−82.5 (3)	C17—C18—C19—C20	0.7 (5)
C5—Co1—C6—C7	−163.9 (3)	C18—C19—C20—C21	−0.6 (5)
C1—Co1—C6—C7	−121.7 (3)	C19—C20—C21—C22	0.3 (5)
C8—Co1—C6—C7	37.89 (19)	C18—C17—C22—C21	0.2 (4)
C9—Co1—C6—C7	81.8 (2)	P1—C17—C22—C21	178.4 (2)
C10—Co1—C6—C7	119.7 (3)	C20—C21—C22—C17	−0.1 (5)
C3—Co1—C6—C10	−170.6 (3)	C9—C10—P1—C17	124.5 (3)
C2—Co1—C6—C10	157.8 (3)	C6—C10—P1—C17	−60.6 (3)
C5—Co1—C6—C10	76.4 (3)	Co1—C10—P1—C17	−146.42 (14)
C1—Co1—C6—C10	118.7 (3)	C9—C10—P1—C11	18.2 (3)
C7—Co1—C6—C10	−119.7 (3)	C6—C10—P1—C11	−166.8 (2)
C8—Co1—C6—C10	−81.77 (19)	Co1—C10—P1—C11	107.31 (16)
C9—Co1—C6—C10	−37.87 (17)	C22—C17—P1—C10	−18.3 (3)
C10—C6—C7—C8	0.4 (3)	C18—C17—P1—C10	160.0 (2)
Co1—C6—C7—C8	−59.6 (2)	C22—C17—P1—C11	85.6 (3)
C10—C6—C7—Co1	59.9 (2)	C18—C17—P1—C11	−96.2 (2)
C3—Co1—C7—C6	153.4 (3)	C12—C11—P1—C10	−81.0 (2)
C4—Co1—C7—C6	−176.4 (3)	C16—C11—P1—C10	103.4 (3)
C2—Co1—C7—C6	114.7 (3)	C12—C11—P1—C17	174.7 (2)
C5—Co1—C7—C6	56.0 (6)	C16—C11—P1—C17	−0.9 (3)
C1—Co1—C7—C6	78.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···F2	0.98	2.45	3.133 (4)	127
C6—H6···F4^i	0.98	2.36	3.270 (5)	155
C4—H4···F3^ii	0.98	2.33	3.215 (5)	150
C1—H1···F5^i	0.98	2.51	3.167 (6)	124

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