An ortho­rhom­bic polymorph of dichloro­tris(penta­fluoro­phen­yl)phospho­rane

Barnes, N.A.; Godfrey, S.M.; Halton, R.T.A.; Mushtaq, I.; Pritchard, R.G.

doi:10.1107/S1600536806021751

organic compounds

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ISSN: 2056-9890

Volume 62| Part 7| July 2006| Pages o2872-o2874

https://doi.org/10.1107/S1600536806021751

An orthorhombic polymorph of dichlorotris(pentafluorophenyl)phosphorane

Nicholas A. Barnes,^a Stephen M. Godfrey,^a ^* Ruth T. A. Halton,^a Imrana Mushtaq ^a and Robin G. Pritchard ^a

^aSchool of Chemistry, The University of Manchester (North Campus), Manchester M60 1QD, England
^*Correspondence e-mail: stephen.m.godfrey@manchester.ac.uk

(Received 5 June 2006; accepted 8 June 2006; online 16 June 2006)

An orthorhombic form of dichlorotris(pentafluorophenyl)phosphorane, C₁₈Cl₂F₁₅P, has been obtained as the product of the reaction between PhSeCl and (C₆F₅)₃P, and is a polymorph of the previously reported monoclinic form obtained from the reaction of (C₆F₅)₃P with Cl₂. The molecule displays nearly perfect trigonal–bipyramidal geometry, and features a number of intermolecular F⋯F contacts, which lead to fluorous domains in the crystal packing.

Comment

Compounds of formula R₃PCl₂ are usually ionic in the solid state (Dillon et al., 1976 ; Godfrey et al., 1996 , 1997 ; Ruthe et al., 1997 ) and solution (Beveridge et al., 1966 ; Wiley & Stine, 1967 ; Harris & Ali, 1968 ; Godfrey et al., 1997); however, molecular five-coordinate trigonal–bipyramidal structures have been observed for R₃ = Ph₃, (C₆F₅)Ph₂ and (C₆F₅)₃ (Godfrey et al., 1997; Godfrey, McAuliffe, Pritchard & Sheffield, 1998 ). Whilst the trigonal–bipyramidal form of Ph₃PCl₂ ionizes in solution, the analogous compounds containing highly electron withdrawing C₆F₅ groups retain their trigonal–bipyramidal geometry in solution. We have previously described the structure of the monoclinic form of (C₆F₅)₃PCl₂ (space group P2₁/c), prepared from (C₆F₅)₃P and dichlorine (Godfrey et al., 1997). We now report that the same compound is also formed when phenylselenenyl chloride is reacted with (C₆F₅)₃P; however the crystals obtained were an orthorhombic polymorph of (C₆F₅)₃PCl₂, (I) (see Fig. 1 and Table 1).

Compound (I) displays nearly perfect trigonal–bipyramidal geometry, although neither of the two polymorphs of (C₆F₅)₃PCl₂ display crystallographically imposed D₃ symmetry, unlike the analogous trigonal–bipyramidal (C₆F₅)₃PBr₂, space group R $[\overline{3}]$ c (Godfrey, McAuliffe, Mushtaq et al., 1998 ). The P—Cl bonds in (I) are nearly equivalent and slightly shorter than observed in the monoclinic polymorph [P—Cl = 2.211 (2) Å; Godfrey et al., 1997]. However, the P—Cl bonds are rather shorter than observed for (C₆F₅)Ph₂PCl₂ [P—Cl = 2.244 (2) and 2.241 (3) Å; Godfrey et al., 1997] and Ph₃PCl₂ [P—Cl = 2.225 (1)–2.280 (2) Å; Godfrey, McAuliffe, Pritchard & Sheffield, 1998), reflecting the increased net electron-withdrawing capability of three C₆F₅ groups. The Cl—P—Cl angle is essentially linear, and the remaining angles around the P atom are close to ideal trigonal–bipyramidal geometry. The C—F bonds in the molecule vary in distance between 1.329 (3) and 1.349 (3) Å, with the C—F bonds to the para-F atoms being the shortest in each C₆F₅ group. A number of intermolecular F⋯F interactions, shorter than the sum of the van der Waals radii of two F atoms, (2.94 Å), are observed, which vary in length between 2.700 (2) Å and 2.900 (2) Å. The extended structure thus features extensive aggregation of the fluorous domains.

Figure 1
The structure of (I)

. Displacement ellipsoids are shown at the 30% probability level.

Experimental

The title compound was prepared by addition of (C₆F₅)₃P (Aldrich) (0.273 g, 5.0 × 10 ⁻⁴ mol) to a freshly distilled diethyl ether solution (50 ml) containing PhSeCl (Aldrich) (0.196 g, 1.0 × 10⁻³ mol). The colour of the solution gradually changed from orange to yellow over several days. The solvent was reduced in volume to 10 ml, and colourless crystals of (I) formed at 273 K over several weeks. The spectroscopic data of (I) match the literature values (Godfrey et al., 1997).

Crystal data

C₁₈Cl₂F₁₅P
M_r = 603.05
Orthorhombic, P b c a
a = 16.7367 (5) Å
b = 11.3713 (2) Å
c = 19.9214 (5) Å
V = 3791.40 (16) Å³
Z = 8
D_x = 2.113 Mg m⁻³
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 150 (2) K
Prism, colourless
0.2 × 0.15 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.893, T_max = 0.944
19042 measured reflections
3458 independent reflections
2634 reflections with I > 2σ(I)
R_int = 0.071
θ_max = 25.3°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.101
S = 1.02
3458 reflections
325 parameters
w = 1/[σ²(F_o²) + (0.0439P)² + 3.0443P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C1—P1	1.820 (3)
C7—P1	1.819 (3)
C13—P1	1.821 (3)
P1—Cl2	2.1995 (10)
P1—Cl1	2.2005 (10)

C7—P1—C1	118.64 (13)
C7—P1—C13	121.49 (13)
C1—P1—C13	119.86 (13)
C7—P1—Cl2	90.26 (9)
C1—P1—Cl2	90.37 (9)
C13—P1—Cl2	89.51 (9)
C7—P1—Cl1	90.12 (9)
C1—P1—Cl1	90.01 (9)
C13—P1—Cl1	89.74 (9)
Cl2—P1—Cl1	179.25 (5)

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536806021751/sg2035sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806021751/sg2035Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

dichlorotris(pentafluorophenyl)phosphorane top

Crystal data top

C₁₈Cl₂F₁₅P	F(000) = 2336
M_r = 603.05	D_x = 2.113 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 10582 reflections
a = 16.7367 (5) Å	θ = 1.0–25.4°
b = 11.3713 (2) Å	µ = 0.58 mm⁻¹
c = 19.9214 (5) Å	T = 150 K
V = 3791.40 (16) Å³	Prism, colourless
Z = 8	0.2 × 0.15 × 0.1 mm

Data collection top

Nonius KappaCCD diffractometer	3458 independent reflections
Radiation source: Enraf Nonius FR590	2634 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 9 pixels mm^-1	θ_max = 25.3°, θ_min = 3.0°
φ or ω scans?	h = −20→16
Absorption correction: multi-scan (Blessing, 1995)	k = −13→13
T_min = 0.893, T_max = 0.944	l = −23→23
19042 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.039	Secondary atom site location: difference Fourier map
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0439P)² + 3.0443P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3458 reflections	Δρ_max = 0.38 e Å⁻³
325 parameters	Δρ_min = −0.54 e Å⁻³

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

	x	y	z	U_iso*/U_eq
C1	0.49075 (17)	0.6096 (2)	0.37260 (13)	0.0238 (6)
C2	0.55870 (17)	0.5387 (2)	0.37278 (14)	0.0260 (6)
C3	0.55340 (19)	0.4188 (3)	0.37960 (14)	0.0299 (7)
C4	0.48042 (19)	0.3638 (2)	0.38180 (13)	0.0292 (7)
C5	0.41183 (18)	0.4310 (2)	0.37903 (14)	0.0286 (7)
C6	0.41747 (17)	0.5513 (2)	0.37650 (14)	0.0258 (6)
C7	0.41500 (17)	0.8501 (2)	0.33031 (14)	0.0247 (6)
C8	0.37070 (17)	0.7999 (2)	0.27868 (13)	0.0258 (6)
C9	0.30550 (17)	0.8560 (2)	0.25108 (13)	0.0270 (6)
C10	0.28672 (18)	0.9685 (3)	0.27131 (15)	0.0303 (7)
C11	0.33072 (18)	1.0219 (2)	0.32053 (15)	0.0290 (7)
C12	0.39230 (18)	0.9622 (2)	0.35101 (14)	0.0277 (6)
C13	0.58145 (17)	0.8449 (2)	0.40678 (14)	0.0262 (6)
C14	0.62486 (17)	0.7936 (2)	0.45900 (13)	0.0254 (6)
C15	0.69123 (19)	0.8466 (3)	0.48534 (14)	0.0308 (7)
C16	0.71409 (18)	0.9565 (3)	0.46304 (15)	0.0333 (7)
C17	0.67161 (19)	1.0105 (2)	0.41272 (15)	0.0307 (7)
C18	0.60700 (18)	0.9538 (2)	0.38398 (14)	0.0280 (6)
F2	0.63189 (10)	0.58597 (14)	0.36801 (8)	0.0314 (4)
F3	0.62094 (11)	0.35433 (14)	0.38288 (8)	0.0384 (4)
F4	0.47576 (12)	0.24731 (14)	0.38598 (8)	0.0389 (5)
F5	0.33989 (11)	0.37926 (14)	0.37902 (9)	0.0381 (4)
F6	0.34878 (10)	0.61209 (14)	0.37595 (8)	0.0310 (4)
F8	0.38919 (10)	0.69310 (13)	0.25486 (8)	0.0298 (4)
F9	0.26056 (10)	0.80222 (16)	0.20460 (8)	0.0367 (4)
F10	0.22484 (11)	1.02353 (16)	0.24344 (9)	0.0443 (5)
F11	0.31355 (11)	1.13189 (13)	0.33964 (9)	0.0398 (4)
F12	0.43149 (10)	1.01566 (14)	0.40148 (8)	0.0327 (4)
F14	0.60279 (10)	0.68909 (13)	0.48410 (8)	0.0296 (4)
F15	0.73410 (11)	0.79176 (17)	0.53271 (8)	0.0426 (5)
F16	0.77747 (12)	1.00955 (17)	0.49033 (9)	0.0480 (5)
F17	0.69268 (12)	1.11803 (14)	0.39190 (9)	0.0415 (5)
F18	0.56887 (10)	1.00802 (14)	0.33355 (9)	0.0342 (4)
P1	0.49612 (4)	0.76936 (6)	0.36995 (3)	0.02308 (18)
Cl1	0.43366 (4)	0.77888 (6)	0.46700 (3)	0.02886 (19)
Cl2	0.55989 (4)	0.76107 (6)	0.27353 (3)	0.02870 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0251 (16)	0.0259 (14)	0.0204 (13)	−0.0007 (11)	0.0001 (11)	0.0002 (11)
C2	0.0227 (16)	0.0316 (15)	0.0238 (14)	−0.0006 (12)	0.0013 (11)	0.0023 (12)
C3	0.0336 (18)	0.0323 (15)	0.0237 (14)	0.0099 (13)	0.0007 (12)	0.0003 (12)
C4	0.046 (2)	0.0198 (13)	0.0220 (14)	−0.0004 (13)	−0.0044 (13)	0.0037 (11)
C5	0.0314 (17)	0.0295 (14)	0.0250 (14)	−0.0077 (13)	−0.0021 (12)	0.0039 (12)
C6	0.0247 (16)	0.0280 (14)	0.0246 (14)	0.0011 (12)	−0.0009 (11)	0.0001 (12)
C7	0.0231 (15)	0.0249 (13)	0.0261 (14)	0.0012 (11)	−0.0001 (12)	0.0030 (12)
C8	0.0263 (16)	0.0266 (14)	0.0245 (14)	0.0003 (12)	0.0035 (12)	0.0013 (12)
C9	0.0208 (15)	0.0369 (15)	0.0234 (14)	−0.0012 (12)	0.0003 (12)	0.0021 (12)
C10	0.0218 (16)	0.0377 (16)	0.0314 (16)	0.0071 (13)	0.0010 (13)	0.0069 (13)
C11	0.0257 (16)	0.0245 (14)	0.0367 (17)	0.0046 (12)	0.0086 (13)	0.0016 (12)
C12	0.0279 (16)	0.0296 (14)	0.0255 (14)	−0.0026 (12)	0.0018 (12)	−0.0009 (12)
C13	0.0274 (16)	0.0257 (14)	0.0256 (14)	−0.0014 (12)	0.0030 (12)	−0.0020 (12)
C14	0.0246 (16)	0.0282 (14)	0.0232 (14)	−0.0010 (12)	0.0027 (11)	0.0029 (12)
C15	0.0295 (17)	0.0419 (17)	0.0211 (14)	−0.0017 (14)	−0.0034 (12)	0.0017 (13)
C16	0.0295 (18)	0.0401 (17)	0.0302 (16)	−0.0113 (14)	0.0029 (13)	−0.0053 (14)
C17	0.0333 (18)	0.0278 (14)	0.0311 (15)	−0.0078 (13)	0.0085 (13)	−0.0013 (13)
C18	0.0273 (16)	0.0284 (14)	0.0284 (15)	0.0007 (12)	0.0020 (13)	0.0029 (12)
F2	0.0227 (9)	0.0351 (9)	0.0363 (9)	0.0026 (7)	0.0013 (7)	0.0007 (7)
F3	0.0419 (11)	0.0343 (9)	0.0388 (10)	0.0170 (8)	0.0028 (8)	0.0027 (8)
F4	0.0597 (13)	0.0233 (8)	0.0337 (9)	−0.0009 (8)	−0.0043 (8)	0.0011 (7)
F5	0.0383 (11)	0.0357 (9)	0.0401 (10)	−0.0148 (8)	−0.0026 (8)	0.0054 (8)
F6	0.0230 (9)	0.0333 (9)	0.0366 (9)	−0.0008 (7)	−0.0003 (7)	0.0028 (7)
F8	0.0306 (9)	0.0268 (8)	0.0320 (9)	0.0021 (7)	−0.0031 (7)	−0.0046 (7)
F9	0.0268 (10)	0.0485 (10)	0.0349 (9)	−0.0004 (8)	−0.0066 (8)	−0.0040 (8)
F10	0.0348 (11)	0.0503 (11)	0.0479 (11)	0.0174 (9)	−0.0072 (9)	0.0041 (9)
F11	0.0371 (11)	0.0273 (8)	0.0551 (11)	0.0096 (8)	0.0035 (9)	−0.0028 (8)
F12	0.0322 (10)	0.0288 (8)	0.0370 (10)	−0.0019 (7)	−0.0023 (8)	−0.0069 (7)
F14	0.0314 (10)	0.0284 (8)	0.0290 (8)	−0.0020 (7)	−0.0035 (7)	0.0061 (7)
F15	0.0368 (11)	0.0582 (12)	0.0329 (9)	−0.0098 (9)	−0.0121 (8)	0.0083 (9)
F16	0.0436 (12)	0.0586 (12)	0.0417 (10)	−0.0262 (10)	−0.0081 (9)	−0.0027 (9)
F17	0.0451 (12)	0.0301 (9)	0.0494 (11)	−0.0130 (8)	0.0052 (9)	0.0013 (8)
F18	0.0318 (10)	0.0307 (9)	0.0402 (10)	−0.0011 (7)	−0.0017 (8)	0.0103 (8)
P1	0.0218 (4)	0.0236 (4)	0.0238 (4)	−0.0005 (3)	−0.0001 (3)	0.0009 (3)
Cl1	0.0278 (4)	0.0336 (4)	0.0251 (4)	−0.0002 (3)	0.0038 (3)	−0.0011 (3)
Cl2	0.0264 (4)	0.0358 (4)	0.0239 (3)	0.0008 (3)	0.0031 (3)	0.0018 (3)

Geometric parameters (Å, º) top

C1—C2	1.394 (4)	C10—F10	1.332 (3)
C1—C6	1.396 (4)	C10—C11	1.368 (4)
C1—P1	1.820 (3)	C11—F11	1.339 (3)
C2—F2	1.341 (3)	C11—C12	1.375 (4)
C2—C3	1.373 (4)	C12—F12	1.346 (3)
C3—F3	1.349 (3)	C13—C18	1.387 (4)
C3—C4	1.373 (4)	C13—C14	1.396 (4)
C4—F4	1.329 (3)	C13—P1	1.821 (3)
C4—C5	1.381 (4)	C14—F14	1.342 (3)
C5—F5	1.340 (3)	C14—C15	1.368 (4)
C5—C6	1.372 (4)	C15—F15	1.340 (3)
C6—F6	1.341 (3)	C15—C16	1.381 (4)
C7—C8	1.390 (4)	C16—F16	1.336 (3)
C7—C12	1.393 (4)	C16—C17	1.374 (4)
C7—P1	1.819 (3)	C17—F17	1.339 (3)
C8—F8	1.340 (3)	C17—C18	1.383 (4)
C8—C9	1.379 (4)	C18—F18	1.340 (3)
C9—F9	1.341 (3)	P1—Cl2	2.1995 (10)
C9—C10	1.377 (4)	P1—Cl1	2.2005 (10)

C2—C1—C6	116.3 (3)	C10—C11—C12	120.0 (2)
C2—C1—P1	122.5 (2)	F12—C12—C11	118.2 (2)
C6—C1—P1	121.2 (2)	F12—C12—C7	120.1 (3)
F2—C2—C3	117.6 (3)	C11—C12—C7	121.7 (3)
F2—C2—C1	120.9 (2)	C18—C13—C14	117.1 (3)
C3—C2—C1	121.4 (3)	C18—C13—P1	122.1 (2)
F3—C3—C2	119.4 (3)	C14—C13—P1	120.8 (2)
F3—C3—C4	119.7 (3)	F14—C14—C15	118.1 (2)
C2—C3—C4	120.9 (3)	F14—C14—C13	120.3 (2)
F4—C4—C3	120.6 (3)	C15—C14—C13	121.6 (3)
F4—C4—C5	120.4 (3)	F15—C15—C14	120.0 (3)
C3—C4—C5	119.1 (3)	F15—C15—C16	120.0 (3)
F5—C5—C6	120.0 (3)	C14—C15—C16	120.0 (3)
F5—C5—C4	120.2 (2)	F16—C16—C17	120.4 (3)
C6—C5—C4	119.8 (3)	F16—C16—C15	119.9 (3)
F6—C6—C5	117.1 (3)	C17—C16—C15	119.7 (3)
F6—C6—C1	120.5 (2)	F17—C17—C16	119.8 (3)
C5—C6—C1	122.4 (3)	F17—C17—C18	120.2 (3)
C8—C7—C12	116.7 (3)	C16—C17—C18	119.9 (3)
C8—C7—P1	120.8 (2)	F18—C18—C17	117.9 (2)
C12—C7—P1	122.5 (2)	F18—C18—C13	120.6 (3)
F8—C8—C9	117.5 (2)	C17—C18—C13	121.4 (3)
F8—C8—C7	120.7 (3)	C7—P1—C1	118.64 (13)
C9—C8—C7	121.8 (3)	C7—P1—C13	121.49 (13)
F9—C9—C10	119.9 (3)	C1—P1—C13	119.86 (13)
F9—C9—C8	120.6 (2)	C7—P1—Cl2	90.26 (9)
C10—C9—C8	119.6 (3)	C1—P1—Cl2	90.37 (9)
F10—C10—C11	120.6 (3)	C13—P1—Cl2	89.51 (9)
F10—C10—C9	119.5 (3)	C7—P1—Cl1	90.12 (9)
C11—C10—C9	119.9 (3)	C1—P1—Cl1	90.01 (9)
F11—C11—C10	120.2 (3)	C13—P1—Cl1	89.74 (9)
F11—C11—C12	119.8 (3)	Cl2—P1—Cl1	179.25 (5)

C6—C1—C2—F2	178.8 (2)	C18—C13—C14—F14	179.1 (2)
P1—C1—C2—F2	−2.9 (4)	P1—C13—C14—F14	−1.9 (4)
C6—C1—C2—C3	−2.9 (4)	C18—C13—C14—C15	−1.9 (4)
P1—C1—C2—C3	175.3 (2)	P1—C13—C14—C15	177.1 (2)
F2—C2—C3—F3	1.6 (4)	F14—C14—C15—F15	2.9 (4)
C1—C2—C3—F3	−176.7 (2)	C13—C14—C15—F15	−176.1 (3)
F2—C2—C3—C4	−177.1 (3)	F14—C14—C15—C16	−177.2 (3)
C1—C2—C3—C4	4.6 (4)	C13—C14—C15—C16	3.8 (4)
F3—C3—C4—F4	−1.2 (4)	F15—C15—C16—F16	−2.2 (4)
C2—C3—C4—F4	177.6 (2)	C14—C15—C16—F16	177.9 (3)
F3—C3—C4—C5	179.4 (2)	F15—C15—C16—C17	177.6 (3)
C2—C3—C4—C5	−1.9 (4)	C14—C15—C16—C17	−2.3 (4)
F4—C4—C5—F5	−1.5 (4)	F16—C16—C17—F17	−1.5 (4)
C3—C4—C5—F5	178.0 (3)	C15—C16—C17—F17	178.7 (3)
F4—C4—C5—C6	178.3 (2)	F16—C16—C17—C18	178.8 (3)
C3—C4—C5—C6	−2.3 (4)	C15—C16—C17—C18	−1.0 (4)
F5—C5—C6—F6	1.8 (4)	F17—C17—C18—F18	2.5 (4)
C4—C5—C6—F6	−178.0 (2)	C16—C17—C18—F18	−177.9 (3)
F5—C5—C6—C1	−176.3 (3)	F17—C17—C18—C13	−176.8 (3)
C4—C5—C6—C1	3.9 (4)	C16—C17—C18—C13	2.9 (4)
C2—C1—C6—F6	−179.3 (2)	C14—C13—C18—F18	179.3 (2)
P1—C1—C6—F6	2.4 (4)	P1—C13—C18—F18	0.3 (4)
C2—C1—C6—C5	−1.3 (4)	C14—C13—C18—C17	−1.4 (4)
P1—C1—C6—C5	−179.5 (2)	P1—C13—C18—C17	179.6 (2)
C12—C7—C8—F8	178.9 (2)	C8—C7—P1—C1	−28.9 (3)
P1—C7—C8—F8	−3.1 (4)	C12—C7—P1—C1	149.0 (2)
C12—C7—C8—C9	−2.6 (4)	C8—C7—P1—C13	151.3 (2)
P1—C7—C8—C9	175.4 (2)	C12—C7—P1—C13	−30.9 (3)
F8—C8—C9—F9	3.2 (4)	C8—C7—P1—Cl2	61.7 (2)
C7—C8—C9—F9	−175.4 (2)	C12—C7—P1—Cl2	−120.5 (2)
F8—C8—C9—C10	−176.5 (2)	C8—C7—P1—Cl1	−118.9 (2)
C7—C8—C9—C10	4.9 (4)	C12—C7—P1—Cl1	58.9 (2)
F9—C9—C10—F10	−1.3 (4)	C2—C1—P1—C7	150.5 (2)
C8—C9—C10—F10	178.4 (2)	C6—C1—P1—C7	−31.3 (3)
F9—C9—C10—C11	177.6 (3)	C2—C1—P1—C13	−29.7 (3)
C8—C9—C10—C11	−2.7 (4)	C6—C1—P1—C13	148.5 (2)
F10—C10—C11—F11	−2.2 (4)	C2—C1—P1—Cl2	60.0 (2)
C9—C10—C11—F11	178.9 (2)	C6—C1—P1—Cl2	−121.9 (2)
F10—C10—C11—C12	177.1 (3)	C2—C1—P1—Cl1	−119.4 (2)
C9—C10—C11—C12	−1.7 (4)	C6—C1—P1—Cl1	58.8 (2)
F11—C11—C12—F12	2.7 (4)	C18—C13—P1—C7	−27.6 (3)
C10—C11—C12—F12	−176.7 (3)	C14—C13—P1—C7	153.4 (2)
F11—C11—C12—C7	−176.5 (3)	C18—C13—P1—C1	152.5 (2)
C10—C11—C12—C7	4.1 (4)	C14—C13—P1—C1	−26.4 (3)
C8—C7—C12—F12	178.9 (2)	C18—C13—P1—Cl2	62.4 (2)
P1—C7—C12—F12	1.0 (4)	C14—C13—P1—Cl2	−116.6 (2)
C8—C7—C12—C11	−2.0 (4)	C18—C13—P1—Cl1	−117.6 (2)
P1—C7—C12—C11	−179.9 (2)	C14—C13—P1—Cl1	63.4 (2)

Acknowledgements

We are grateful to the Engineering and Physical Sciences Research Council (EPSRC) for a research studentship to RTAH, and also for support of the UMIST X-ray facility (Research Initiative Grant).

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