Tris­(penta­fluoro­phenyl)­phosphine oxide

Crystals of the title compound, (C₆F₅)₃P=O or C₁₈H₁₅OP, have two independent mol­ecules in the asymmetric unit, with average P=O and P-C bond lengths of 1.467 (2) and 1.817 (2) Å, respectively, and an average O=P-C angle of 112.9 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 83 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.096
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O1     ..  C56      =       2.91 Ang.

Alert level C
PLAT040_ALERT_1_C No H-atoms in this Carbon Containing Compound ..          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  F56    ..  O1       =       2.92 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C26      =       2.94 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C36      =       2.98 Ang.

Alert level G
CHEMS02_ALERT_1_G  Please check that you have entered the correct
            _publ_requested_category classification of your compound;
            FI or CI or EI for inorganic; FM or CM or EM for metal-organic;
            FO or CO or EO for organic.
            From the CIF: _publ_requested_category   EO
            From the CIF: _chemical_formula_sum :C18 F15 O1 P1

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1994); cell refinement: SMART; data reduction: SAINT (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick 1997); 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 (Version 1.64; Farrugia, 1999).

(I)

Crystal data

C18F15OP	F(000) = 2128
Mr = 548.15	Dx = 2.042 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.562 (1) Å	Cell parameters from 7905 reflections
b = 20.489 (1) Å	θ = 2–26°
c = 18.303 (1) Å	µ = 0.32 mm^−1
β = 95.95 (1)°	T = 83 K
V = 3566.5 (5) Å^3	Needle, white
Z = 8	0.46 × 0.18 × 0.16 mm

Data collection

Siemens SMART CCD diffractometer	7300 independent reflections
Radiation source: fine-focus sealed tube	5418 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −11→11
Tmin = 0.867, Tmax = 0.951	k = 0→25
14186 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.040	Secondary atom site location: difference Fourier map
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 2.4099P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
7300 reflections	Δρmax = 0.35 e Å^−3
631 parameters	Δρmin = −0.36 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.23271 (7)	0.69048 (3)	0.91508 (3)	0.01770 (14)
O1	0.27916 (18)	0.75340 (8)	0.94725 (9)	0.0235 (4)
F12	−0.08513 (14)	0.63627 (7)	0.90415 (8)	0.0251 (3)
F13	−0.20422 (15)	0.57365 (7)	1.00707 (9)	0.0322 (4)
F14	−0.06004 (18)	0.55080 (8)	1.14085 (9)	0.0375 (4)
F15	0.21150 (17)	0.59042 (8)	1.16792 (8)	0.0340 (4)
F16	0.34134 (15)	0.64740 (7)	1.06102 (8)	0.0275 (3)
F22	0.12257 (17)	0.81180 (7)	0.82694 (9)	0.0314 (4)
F23	−0.04231 (18)	0.81450 (9)	0.69968 (10)	0.0441 (5)
F24	−0.13147 (17)	0.70183 (10)	0.63239 (9)	0.0448 (5)
F25	−0.05302 (17)	0.58501 (8)	0.69331 (9)	0.0403 (4)
F26	0.11380 (15)	0.58111 (7)	0.82116 (8)	0.0259 (3)
F32	0.31904 (16)	0.54072 (7)	0.94494 (9)	0.0300 (4)
F33	0.54156 (17)	0.47978 (7)	0.90027 (9)	0.0371 (4)
F34	0.72242 (15)	0.54452 (8)	0.82097 (9)	0.0334 (4)
F35	0.67566 (16)	0.67142 (8)	0.78450 (9)	0.0336 (4)
F36	0.45268 (15)	0.73412 (7)	0.82952 (8)	0.0258 (3)
C11	0.1359 (3)	0.64334 (11)	0.97756 (13)	0.0187 (5)
C12	−0.0040 (3)	0.62411 (12)	0.96733 (14)	0.0207 (5)
C13	−0.0693 (3)	0.59247 (12)	1.02085 (15)	0.0245 (6)
C14	0.0031 (3)	0.58050 (12)	1.08850 (14)	0.0255 (6)
C15	0.1413 (3)	0.60008 (12)	1.10181 (14)	0.0255 (6)
C16	0.2054 (3)	0.63048 (12)	1.04686 (14)	0.0215 (5)
C21	0.1221 (2)	0.69569 (12)	0.82870 (13)	0.0194 (5)
C22	0.0816 (3)	0.75479 (13)	0.79595 (14)	0.0241 (6)
C23	−0.0041 (3)	0.75689 (14)	0.72984 (15)	0.0299 (6)
C24	−0.0490 (3)	0.69967 (15)	0.69624 (14)	0.0307 (7)
C25	−0.0096 (3)	0.64023 (14)	0.72671 (14)	0.0274 (6)
C26	0.0764 (2)	0.63927 (12)	0.79168 (14)	0.0213 (5)
C31	0.3790 (2)	0.64076 (12)	0.89025 (13)	0.0192 (5)
C32	0.4050 (3)	0.57518 (12)	0.90656 (14)	0.0227 (5)
C33	0.5196 (3)	0.54295 (12)	0.88333 (15)	0.0263 (6)
C34	0.6110 (3)	0.57556 (13)	0.84291 (14)	0.0244 (6)
C35	0.5875 (3)	0.63994 (13)	0.82485 (14)	0.0239 (6)
C36	0.4730 (3)	0.67152 (12)	0.84864 (13)	0.0212 (5)
P2	0.35787 (6)	0.61940 (3)	0.63562 (3)	0.01802 (14)
O2	0.31295 (18)	0.64998 (8)	0.70178 (9)	0.0235 (4)
F42	0.20850 (14)	0.51079 (7)	0.69146 (8)	0.0282 (3)
F43	0.30154 (16)	0.39320 (7)	0.74170 (9)	0.0335 (4)
F44	0.57237 (17)	0.35809 (7)	0.73119 (9)	0.0329 (4)
F45	0.75148 (15)	0.44183 (7)	0.67415 (8)	0.0303 (4)
F46	0.66368 (14)	0.55963 (7)	0.62693 (8)	0.0259 (3)
F52	0.26525 (15)	0.49966 (7)	0.52869 (8)	0.0250 (3)
F53	0.06359 (15)	0.50076 (7)	0.41726 (8)	0.0259 (3)
F54	−0.09423 (15)	0.60924 (8)	0.38647 (8)	0.0321 (4)
F55	−0.04669 (16)	0.71843 (7)	0.46979 (9)	0.0311 (4)
F56	0.15452 (15)	0.71893 (7)	0.58287 (8)	0.0239 (3)
F62	0.48754 (16)	0.75316 (7)	0.67759 (8)	0.0278 (3)
F63	0.64005 (16)	0.82941 (7)	0.59837 (8)	0.0292 (4)
F64	0.71166 (15)	0.78893 (7)	0.46668 (8)	0.0273 (3)
F65	0.63732 (15)	0.66753 (7)	0.41587 (8)	0.0276 (3)
F66	0.48424 (14)	0.58921 (7)	0.49495 (8)	0.0231 (3)
C41	0.4315 (3)	0.53937 (11)	0.65708 (13)	0.0192 (5)
C42	0.3442 (3)	0.49489 (13)	0.68782 (14)	0.0230 (5)
C43	0.3889 (3)	0.43455 (12)	0.71302 (14)	0.0238 (6)
C44	0.5271 (3)	0.41673 (12)	0.70806 (14)	0.0240 (6)
C45	0.6178 (3)	0.45921 (12)	0.67844 (13)	0.0217 (5)
C46	0.5702 (3)	0.51967 (12)	0.65374 (13)	0.0198 (5)
C51	0.2171 (2)	0.60933 (12)	0.56150 (13)	0.0191 (5)
C52	0.1903 (2)	0.55510 (11)	0.51676 (14)	0.0203 (5)
C53	0.0867 (3)	0.55441 (12)	0.45831 (13)	0.0214 (5)
C54	0.0055 (3)	0.60920 (13)	0.44328 (14)	0.0240 (6)
C55	0.0285 (2)	0.66413 (12)	0.48607 (14)	0.0219 (5)
C56	0.1329 (3)	0.66379 (12)	0.54381 (13)	0.0201 (5)
C61	0.4804 (2)	0.66790 (12)	0.58920 (13)	0.0181 (5)
C62	0.5223 (2)	0.73001 (12)	0.61365 (13)	0.0197 (5)
C63	0.6007 (3)	0.77026 (11)	0.57303 (14)	0.0217 (5)
C64	0.6382 (2)	0.74960 (12)	0.50661 (14)	0.0211 (5)
C65	0.5999 (2)	0.68779 (12)	0.48056 (13)	0.0212 (5)
C66	0.5225 (2)	0.64887 (11)	0.52178 (13)	0.0190 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0180 (3)	0.0169 (3)	0.0180 (3)	−0.0011 (2)	0.0013 (2)	0.0001 (3)
O1	0.0245 (9)	0.0220 (9)	0.0239 (10)	−0.0031 (7)	0.0021 (7)	−0.0026 (7)
F12	0.0200 (7)	0.0314 (8)	0.0233 (8)	−0.0030 (6)	−0.0003 (6)	0.0018 (6)
F13	0.0254 (8)	0.0339 (9)	0.0379 (9)	−0.0107 (7)	0.0068 (7)	0.0042 (7)
F14	0.0487 (10)	0.0336 (9)	0.0318 (9)	−0.0098 (8)	0.0121 (8)	0.0101 (7)
F15	0.0434 (10)	0.0362 (9)	0.0213 (8)	0.0000 (7)	−0.0022 (7)	0.0082 (7)
F16	0.0239 (8)	0.0318 (8)	0.0253 (8)	−0.0044 (6)	−0.0048 (6)	0.0029 (7)
F22	0.0371 (9)	0.0198 (8)	0.0375 (9)	−0.0004 (7)	0.0041 (7)	0.0048 (7)
F23	0.0422 (10)	0.0503 (11)	0.0394 (10)	0.0131 (8)	0.0019 (8)	0.0237 (8)
F24	0.0282 (9)	0.0813 (14)	0.0230 (9)	0.0127 (9)	−0.0065 (7)	0.0013 (9)
F25	0.0304 (9)	0.0525 (11)	0.0360 (10)	0.0017 (8)	−0.0061 (7)	−0.0241 (8)
F26	0.0266 (8)	0.0208 (7)	0.0293 (8)	0.0003 (6)	−0.0015 (6)	−0.0048 (6)
F32	0.0332 (8)	0.0213 (8)	0.0367 (9)	−0.0003 (7)	0.0091 (7)	0.0056 (7)
F33	0.0415 (10)	0.0227 (8)	0.0473 (10)	0.0110 (7)	0.0047 (8)	0.0025 (7)
F34	0.0240 (8)	0.0384 (9)	0.0378 (9)	0.0083 (7)	0.0029 (7)	−0.0089 (7)
F35	0.0276 (8)	0.0393 (9)	0.0360 (9)	0.0000 (7)	0.0139 (7)	0.0015 (7)
F36	0.0285 (8)	0.0219 (8)	0.0281 (8)	0.0005 (6)	0.0076 (6)	0.0033 (6)
C11	0.0226 (12)	0.0151 (12)	0.0188 (13)	0.0002 (10)	0.0037 (10)	−0.0002 (10)
C12	0.0236 (13)	0.0188 (12)	0.0195 (13)	0.0007 (10)	0.0010 (10)	−0.0014 (10)
C13	0.0220 (13)	0.0215 (13)	0.0304 (15)	−0.0038 (10)	0.0046 (11)	−0.0015 (11)
C14	0.0371 (15)	0.0179 (13)	0.0229 (14)	−0.0024 (11)	0.0098 (12)	0.0027 (11)
C15	0.0357 (15)	0.0210 (13)	0.0188 (13)	0.0008 (11)	−0.0016 (11)	0.0027 (11)
C16	0.0231 (13)	0.0182 (12)	0.0229 (13)	−0.0018 (10)	0.0013 (10)	−0.0016 (10)
C21	0.0154 (12)	0.0231 (13)	0.0198 (13)	−0.0002 (10)	0.0025 (10)	−0.0015 (10)
C22	0.0220 (13)	0.0258 (14)	0.0256 (14)	0.0015 (11)	0.0081 (11)	0.0044 (11)
C23	0.0243 (14)	0.0399 (17)	0.0265 (15)	0.0098 (12)	0.0073 (11)	0.0141 (13)
C24	0.0169 (13)	0.061 (2)	0.0143 (13)	0.0082 (13)	0.0007 (10)	0.0009 (13)
C25	0.0178 (13)	0.0417 (17)	0.0230 (14)	0.0022 (12)	0.0034 (10)	−0.0103 (12)
C26	0.0163 (12)	0.0247 (13)	0.0233 (13)	0.0022 (10)	0.0040 (10)	−0.0017 (11)
C31	0.0184 (12)	0.0199 (12)	0.0187 (12)	−0.0004 (10)	−0.0012 (10)	−0.0017 (10)
C32	0.0255 (13)	0.0223 (13)	0.0203 (13)	−0.0016 (10)	0.0016 (11)	−0.0006 (10)
C33	0.0293 (14)	0.0198 (13)	0.0283 (15)	0.0053 (11)	−0.0046 (11)	0.0010 (11)
C34	0.0196 (13)	0.0300 (14)	0.0230 (14)	0.0057 (11)	−0.0014 (10)	−0.0080 (11)
C35	0.0202 (13)	0.0310 (14)	0.0203 (13)	−0.0023 (11)	0.0014 (10)	−0.0018 (11)
C36	0.0240 (13)	0.0204 (12)	0.0185 (13)	0.0002 (10)	−0.0006 (10)	0.0004 (10)
P2	0.0169 (3)	0.0193 (3)	0.0179 (3)	0.0000 (2)	0.0021 (2)	−0.0002 (3)
O2	0.0235 (9)	0.0264 (9)	0.0209 (9)	0.0009 (8)	0.0033 (7)	−0.0027 (8)
F42	0.0189 (7)	0.0312 (8)	0.0347 (9)	−0.0020 (6)	0.0038 (6)	0.0049 (7)
F43	0.0311 (9)	0.0316 (9)	0.0373 (9)	−0.0090 (7)	0.0012 (7)	0.0123 (7)
F44	0.0397 (9)	0.0214 (8)	0.0365 (9)	0.0012 (7)	−0.0019 (7)	0.0076 (7)
F45	0.0264 (8)	0.0297 (8)	0.0355 (9)	0.0106 (7)	0.0070 (7)	0.0073 (7)
F46	0.0196 (7)	0.0256 (8)	0.0334 (9)	0.0011 (6)	0.0068 (6)	0.0088 (6)
F52	0.0266 (8)	0.0204 (7)	0.0271 (8)	0.0042 (6)	−0.0011 (6)	−0.0034 (6)
F53	0.0276 (8)	0.0258 (8)	0.0238 (8)	−0.0077 (6)	0.0011 (6)	−0.0059 (6)
F54	0.0245 (8)	0.0396 (9)	0.0299 (9)	−0.0032 (7)	−0.0086 (7)	0.0001 (7)
F55	0.0273 (8)	0.0276 (8)	0.0368 (9)	0.0084 (7)	−0.0048 (7)	0.0027 (7)
F56	0.0270 (8)	0.0205 (7)	0.0241 (8)	0.0034 (6)	0.0029 (6)	−0.0025 (6)
F62	0.0365 (9)	0.0237 (8)	0.0241 (8)	−0.0030 (7)	0.0074 (7)	−0.0069 (6)
F63	0.0330 (9)	0.0191 (7)	0.0356 (9)	−0.0048 (6)	0.0036 (7)	−0.0033 (7)
F64	0.0232 (8)	0.0271 (8)	0.0322 (9)	−0.0024 (6)	0.0058 (6)	0.0079 (7)
F65	0.0291 (8)	0.0344 (9)	0.0210 (8)	−0.0007 (7)	0.0100 (6)	−0.0019 (7)
F66	0.0245 (7)	0.0218 (7)	0.0237 (8)	−0.0018 (6)	0.0053 (6)	−0.0059 (6)
C41	0.0221 (12)	0.0195 (12)	0.0156 (12)	−0.0004 (10)	0.0006 (10)	−0.0011 (10)
C42	0.0205 (13)	0.0272 (14)	0.0206 (13)	−0.0028 (11)	−0.0007 (10)	−0.0007 (11)
C43	0.0281 (14)	0.0230 (13)	0.0198 (13)	−0.0087 (11)	0.0004 (11)	0.0031 (10)
C44	0.0332 (14)	0.0182 (13)	0.0193 (13)	0.0017 (11)	−0.0034 (11)	0.0018 (10)
C45	0.0222 (13)	0.0235 (13)	0.0191 (13)	0.0022 (10)	0.0002 (10)	−0.0016 (10)
C46	0.0215 (13)	0.0215 (13)	0.0163 (12)	−0.0022 (10)	0.0017 (10)	−0.0008 (10)
C51	0.0170 (12)	0.0228 (13)	0.0178 (12)	−0.0013 (10)	0.0039 (10)	0.0002 (10)
C52	0.0186 (12)	0.0186 (12)	0.0243 (14)	0.0003 (10)	0.0054 (10)	0.0009 (10)
C53	0.0209 (12)	0.0245 (13)	0.0196 (13)	−0.0063 (10)	0.0069 (10)	−0.0017 (11)
C54	0.0167 (12)	0.0343 (15)	0.0206 (13)	−0.0045 (11)	0.0003 (10)	0.0017 (11)
C55	0.0164 (12)	0.0247 (13)	0.0248 (14)	0.0039 (10)	0.0029 (10)	0.0033 (11)
C56	0.0204 (12)	0.0191 (12)	0.0213 (13)	−0.0011 (10)	0.0057 (10)	−0.0004 (10)
C61	0.0156 (12)	0.0206 (12)	0.0179 (12)	0.0027 (9)	0.0001 (9)	0.0005 (10)
C62	0.0180 (12)	0.0220 (13)	0.0189 (13)	0.0042 (10)	0.0015 (10)	−0.0020 (10)
C63	0.0205 (13)	0.0165 (12)	0.0274 (14)	0.0024 (10)	−0.0016 (10)	−0.0004 (11)
C64	0.0146 (12)	0.0227 (13)	0.0259 (14)	0.0010 (10)	0.0016 (10)	0.0089 (11)
C65	0.0174 (12)	0.0283 (14)	0.0181 (13)	0.0046 (10)	0.0022 (10)	0.0016 (11)
C66	0.0172 (12)	0.0182 (12)	0.0209 (13)	0.0022 (10)	−0.0013 (10)	−0.0015 (10)

Geometric parameters (Å, º)

P1—O1	1.4670 (17)	P2—O2	1.4667 (18)
P1—C21	1.812 (2)	P2—C41	1.811 (2)
P1—C11	1.821 (2)	P2—C61	1.813 (3)
P1—C31	1.826 (3)	P2—C51	1.821 (2)
F12—C12	1.347 (3)	F42—C42	1.346 (3)
F13—C13	1.345 (3)	F43—C43	1.335 (3)
F14—C14	1.332 (3)	F44—C44	1.331 (3)
F15—C15	1.336 (3)	F45—C45	1.337 (3)
F16—C16	1.344 (3)	F46—C46	1.342 (3)
F22—C22	1.339 (3)	F52—C52	1.349 (3)
F23—C23	1.338 (3)	F53—C53	1.337 (3)
F24—C24	1.341 (3)	F54—C54	1.336 (3)
F25—C25	1.332 (3)	F55—C55	1.341 (3)
F26—C26	1.341 (3)	F56—C56	1.342 (3)
F32—C32	1.337 (3)	F62—C62	1.336 (3)
F33—C33	1.342 (3)	F63—C63	1.338 (3)
F34—C34	1.337 (3)	F64—C64	1.335 (3)
F35—C35	1.342 (3)	F65—C65	1.338 (3)
F36—C36	1.338 (3)	F66—C66	1.353 (3)
C11—C12	1.389 (3)	C41—C42	1.393 (3)
C11—C16	1.395 (3)	C41—C46	1.394 (3)
C12—C13	1.377 (4)	C42—C43	1.372 (4)
C13—C14	1.377 (4)	C43—C44	1.383 (4)
C14—C15	1.379 (4)	C44—C45	1.378 (4)
C15—C16	1.379 (4)	C45—C46	1.380 (3)
C21—C26	1.387 (3)	C51—C52	1.388 (3)
C21—C22	1.388 (3)	C51—C56	1.394 (3)
C22—C23	1.390 (4)	C52—C53	1.381 (3)
C23—C24	1.372 (4)	C53—C54	1.376 (4)
C24—C25	1.376 (4)	C54—C55	1.376 (4)
C25—C26	1.374 (4)	C55—C56	1.377 (3)
C31—C36	1.388 (3)	C61—C66	1.393 (3)
C31—C32	1.393 (3)	C61—C62	1.394 (3)
C32—C33	1.383 (4)	C62—C63	1.382 (3)
C33—C34	1.376 (4)	C63—C64	1.370 (4)
C34—C35	1.373 (4)	C64—C65	1.389 (4)
C35—C36	1.380 (3)	C65—C66	1.367 (3)
O1—P1—C21	115.06 (11)	O2—P2—C41	110.37 (11)
O1—P1—C11	111.50 (11)	O2—P2—C61	114.30 (11)
C21—P1—C11	106.87 (11)	C41—P2—C61	110.01 (11)
O1—P1—C31	112.48 (11)	O2—P2—C51	113.97 (11)
C21—P1—C31	102.05 (11)	C41—P2—C51	107.43 (11)
C11—P1—C31	108.23 (11)	C61—P2—C51	100.18 (11)
C12—C11—C16	115.5 (2)	C42—C41—C46	116.1 (2)
C12—C11—P1	127.67 (19)	C42—C41—P2	116.37 (18)
C16—C11—P1	116.46 (18)	C46—C41—P2	127.08 (19)
F12—C12—C13	115.8 (2)	F42—C42—C43	118.0 (2)
F12—C12—C11	121.6 (2)	F42—C42—C41	118.9 (2)
C13—C12—C11	122.6 (2)	C43—C42—C41	123.1 (2)
F13—C13—C14	120.1 (2)	F43—C43—C42	121.2 (2)
F13—C13—C12	119.9 (2)	F43—C43—C44	120.0 (2)
C14—C13—C12	120.0 (2)	C42—C43—C44	118.8 (2)
F14—C14—C13	120.3 (2)	F44—C44—C45	119.9 (2)
F14—C14—C15	120.3 (2)	F44—C44—C43	119.9 (2)
C13—C14—C15	119.4 (2)	C45—C44—C43	120.2 (2)
F15—C15—C14	119.9 (2)	F45—C45—C44	119.9 (2)
F15—C15—C16	120.5 (2)	F45—C45—C46	120.3 (2)
C14—C15—C16	119.5 (2)	C44—C45—C46	119.8 (2)
F16—C16—C15	118.0 (2)	F46—C46—C45	117.3 (2)
F16—C16—C11	119.1 (2)	F46—C46—C41	120.8 (2)
C15—C16—C11	122.8 (2)	C45—C46—C41	121.9 (2)
C26—C21—C22	117.1 (2)	C52—C51—C56	115.9 (2)
C26—C21—P1	120.19 (19)	C52—C51—P2	127.36 (19)
C22—C21—P1	122.66 (19)	C56—C51—P2	116.53 (18)
F22—C22—C21	121.4 (2)	F52—C52—C53	116.3 (2)
F22—C22—C23	117.5 (2)	F52—C52—C51	121.1 (2)
C21—C22—C23	121.1 (2)	C53—C52—C51	122.6 (2)
F23—C23—C24	120.6 (2)	F53—C53—C54	120.1 (2)
F23—C23—C22	119.9 (3)	F53—C53—C52	120.5 (2)
C24—C23—C22	119.5 (2)	C54—C53—C52	119.4 (2)
F24—C24—C23	119.4 (3)	F54—C54—C55	120.1 (2)
F24—C24—C25	119.6 (3)	F54—C54—C53	119.9 (2)
C23—C24—C25	121.0 (2)	C55—C54—C53	120.0 (2)
F25—C25—C26	121.0 (2)	F55—C55—C54	120.1 (2)
F25—C25—C24	120.4 (2)	F55—C55—C56	120.3 (2)
C26—C25—C24	118.5 (2)	C54—C55—C56	119.5 (2)
F26—C26—C25	118.1 (2)	F56—C56—C55	117.7 (2)
F26—C26—C21	119.1 (2)	F56—C56—C51	119.8 (2)
C25—C26—C21	122.7 (2)	C55—C56—C51	122.5 (2)
C36—C31—C32	116.3 (2)	C66—C61—C62	116.1 (2)
C36—C31—P1	116.08 (18)	C66—C61—P2	121.45 (18)
C32—C31—P1	127.55 (19)	C62—C61—P2	121.87 (18)
F32—C32—C33	117.3 (2)	F62—C62—C63	117.2 (2)
F32—C32—C31	121.0 (2)	F62—C62—C61	121.1 (2)
C33—C32—C31	121.6 (2)	C63—C62—C61	121.7 (2)
F33—C33—C34	120.0 (2)	F63—C63—C64	119.8 (2)
F33—C33—C32	119.9 (2)	F63—C63—C62	120.2 (2)
C34—C33—C32	120.1 (2)	C64—C63—C62	120.0 (2)
F34—C34—C35	120.0 (2)	F64—C64—C63	120.0 (2)
F34—C34—C33	120.1 (2)	F64—C64—C65	119.8 (2)
C35—C34—C33	119.9 (2)	C63—C64—C65	120.1 (2)
F35—C35—C34	119.8 (2)	F65—C65—C66	121.1 (2)
F35—C35—C36	120.8 (2)	F65—C65—C64	120.1 (2)
C34—C35—C36	119.3 (2)	C66—C65—C64	118.8 (2)
F36—C36—C35	117.7 (2)	F66—C66—C65	117.9 (2)
F36—C36—C31	119.6 (2)	F66—C66—C61	118.8 (2)
C35—C36—C31	122.7 (2)	C65—C66—C61	123.3 (2)