1,2-Bis[5-(3,5-difluoro­phen­yl)-2-methyl-3-thien­yl]-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-ene: a new photochromic diaryl­ethene compound

The title compound, C₂₇H₁₄F₁₀S₂, is a new symmetrical photochromic diaryl­ethene derivative which can be used potentially for optical recording media and other optoelectronic device materials. The distance between the two reactive C atoms is 3.571 (4) Å. The dihedral angles between the thio­phene rings and the attached benzene rings are 15.2 (6) and 24.7 (7)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.112
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        F6'
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        F7'
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        F8'

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         F3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         F5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        F5'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C14'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT301_ALERT_3_C Main Residue  Disorder .........................      15.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  F8'    ..  C26     ..       2.92 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.40 Deg.
              F3   -C13  -F3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.40 Deg.
              F4   -C13  -F4'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.70 Deg.
              C14' -C13  -C14     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      19.50 Deg.
              F7'  -C15  -F7      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.20 Deg.
              F8'  -C15  -F8      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.60 Deg.
              C14  -C15  -C14'    1.555   1.555   1.555

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

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

---

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, 1997); software used to prepare material for publication: SHELXTL.

1,2-Bis[5-(3,5-difluorophenyl)-2-methyl-3-thienyl]-3,3,4,4,5,5- hexafluorocyclopent-1-ene

Crystal data

C27H14F10S2	Dx = 1.575 Mg m^−3
Mr = 592.50	Melting point: 430.4 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.582 (2) Å	Cell parameters from 3440 reflections
b = 11.552 (2) Å	θ = 2.6–22.6°
c = 16.127 (3) Å	µ = 0.30 mm^−1
β = 99.019 (3)°	T = 294 K
V = 2499.1 (8) Å^3	Prism, colorless
Z = 4	0.24 × 0.20 × 0.14 mm
F(000) = 1192

Data collection

Bruker SMART CCD area-detector diffractometer	4401 independent reflections
Radiation source: fine-focus sealed tube	2811 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→16
Tmin = 0.889, Tmax = 1.000	k = −12→13
12416 measured reflections	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.5704P] where P = (Fo^2 + 2Fc^2)/3
4401 reflections	(Δ/σ)max = 0.002
417 parameters	Δρmax = 0.21 e Å^−3
18 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. ¹³C NMR (100 MHz, CDCl₃) δ 14.57, 103.19, 108.47, 123.95, 126.06, 136.29, 140.00, 142.62, 162.30, 164.79. IR(KBr, cm_-1) ν 540, 674, 741, 796, 874, 989, 1119, 1141, 11743, 1278, 1309, 1340, 1441, 1593, 1624, 2920, 2964.

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. It was obvious from electron-density maps that the CF₂ group at C14 was disordered corresponding with two orientations of the cyclopent-1-ene ring in a C14-envelope conformation. Initially the two disordered orientations were refined with tied occupancy parameters, but as these refined occupancy values were not significantly different from 1/2, the occupancies were then fixed at 0.5 for the final refinement cycles.

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)
S1	0.42439 (5)	0.87721 (7)	0.08251 (5)	0.0639 (2)
S2	0.36986 (5)	0.59328 (6)	0.36711 (6)	0.0693 (3)
F1	0.26356 (15)	1.23070 (19)	−0.08961 (12)	0.1035 (7)
F2	0.3826 (2)	1.41200 (18)	0.16413 (14)	0.1208 (8)
F3	0.7269 (10)	1.0058 (6)	0.3143 (6)	0.098 (3)	0.50
F4	0.7912 (4)	0.8648 (6)	0.2494 (3)	0.0988 (19)	0.50
F5	0.8765 (6)	0.8204 (9)	0.3970 (7)	0.098 (3)	0.50
F6	0.7584 (3)	0.8994 (3)	0.4545 (2)	0.0903 (12)	0.50
F7	0.7766 (9)	0.6336 (8)	0.3665 (9)	0.084 (3)	0.50
F8	0.7112 (4)	0.6850 (4)	0.4700 (3)	0.0732 (14)	0.50
C14	0.7776 (5)	0.8319 (8)	0.3919 (5)	0.063 (2)	0.50
F3'	0.7164 (9)	0.9905 (5)	0.3469 (6)	0.086 (3)	0.50
F4'	0.7614 (4)	0.9346 (5)	0.2332 (4)	0.0896 (17)	0.50
F5'	0.8473 (3)	0.7538 (4)	0.2983 (3)	0.1133 (15)	0.50
F6'	0.8625 (7)	0.8613 (10)	0.4123 (7)	0.114 (4)	0.50
F7'	0.7622 (9)	0.6177 (9)	0.3872 (9)	0.104 (5)	0.50
F8'	0.7236 (5)	0.7572 (6)	0.4695 (3)	0.1044 (19)	0.50
C14'	0.7970 (5)	0.8120 (8)	0.3514 (5)	0.068 (2)	0.50
F9	0.56467 (18)	0.09962 (19)	0.4403 (2)	0.1372 (10)
F10	0.22996 (16)	0.17087 (18)	0.34050 (17)	0.1271 (9)
C1	0.35592 (19)	1.1227 (3)	0.01803 (18)	0.0638 (8)
H1	0.3485	1.0576	−0.0163	0.077*
C2	0.3143 (2)	1.2263 (3)	−0.01045 (19)	0.0701 (9)
C3	0.3223 (2)	1.3247 (3)	0.0363 (2)	0.0743 (9)
H3	0.2937	1.3941	0.0154	0.089*
C4	0.3743 (3)	1.3164 (3)	0.1154 (2)	0.0739 (9)
C5	0.4173 (2)	1.2156 (3)	0.14823 (18)	0.0641 (8)
H5	0.4514	1.2138	0.2029	0.077*
C6	0.40955 (18)	1.1164 (2)	0.09913 (17)	0.0527 (7)
C7	0.45660 (18)	1.0077 (2)	0.13191 (16)	0.0524 (7)
C8	0.52806 (18)	0.9895 (2)	0.19998 (16)	0.0522 (7)
H8	0.5564	1.0491	0.2345	0.063*
C9	0.55546 (18)	0.8715 (2)	0.21374 (16)	0.0482 (6)
C10	0.50569 (19)	0.7992 (2)	0.15386 (16)	0.0542 (7)
C11	0.5146 (2)	0.6710 (2)	0.14256 (19)	0.0703 (8)
H11A	0.5813	0.6468	0.1643	0.105*
H11B	0.5000	0.6524	0.0839	0.105*
H11C	0.4684	0.6319	0.1722	0.105*
C12	0.63066 (17)	0.8307 (2)	0.28348 (16)	0.0479 (6)
C13	0.7290 (2)	0.8917 (3)	0.30427 (18)	0.0615 (8)
C15	0.7243 (2)	0.7230 (3)	0.39039 (18)	0.0603 (7)
C16	0.62652 (18)	0.7402 (2)	0.33507 (15)	0.0465 (6)
C17	0.54170 (18)	0.6641 (2)	0.34612 (15)	0.0480 (6)
C18	0.4480 (2)	0.7046 (2)	0.35152 (18)	0.0570 (7)
C19	0.4106 (2)	0.8269 (3)	0.3491 (2)	0.0871 (11)
H19A	0.4646	0.8781	0.3696	0.131*
H19B	0.3595	0.8336	0.3838	0.131*
H19C	0.3836	0.8474	0.2924	0.131*
C20	0.54882 (19)	0.5419 (2)	0.35543 (15)	0.0510 (6)
H20	0.6076	0.5010	0.3543	0.061*
C21	0.46187 (19)	0.4906 (2)	0.36612 (16)	0.0522 (7)
C22	0.4392 (2)	0.3671 (2)	0.37453 (16)	0.0539 (7)
C23	0.5144 (2)	0.2897 (3)	0.4044 (2)	0.0730 (9)
H23	0.5798	0.3148	0.4195	0.088*
C24	0.4902 (3)	0.1750 (3)	0.4111 (2)	0.0822 (10)
C25	0.3961 (3)	0.1331 (3)	0.3903 (2)	0.0880 (11)
H25	0.3818	0.0549	0.3955	0.106*
C26	0.3242 (3)	0.2107 (3)	0.3614 (2)	0.0785 (9)
C27	0.3426 (2)	0.3254 (3)	0.35233 (18)	0.0646 (8)
H27	0.2911	0.3755	0.3314	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0620 (5)	0.0676 (5)	0.0571 (4)	−0.0071 (4)	−0.0063 (4)	−0.0032 (4)
S2	0.0553 (4)	0.0573 (5)	0.1026 (6)	0.0009 (3)	0.0349 (4)	0.0031 (4)
F1	0.0922 (14)	0.1349 (18)	0.0747 (13)	0.0293 (12)	−0.0141 (11)	0.0175 (12)
F2	0.189 (2)	0.0699 (13)	0.0986 (15)	0.0228 (14)	0.0082 (15)	−0.0023 (12)
F3	0.086 (4)	0.075 (4)	0.121 (7)	−0.041 (3)	−0.027 (5)	0.027 (4)
F4	0.059 (3)	0.165 (6)	0.076 (3)	−0.029 (3)	0.022 (3)	0.001 (4)
F5	0.038 (3)	0.127 (7)	0.128 (5)	−0.011 (3)	0.006 (3)	0.017 (4)
F6	0.125 (3)	0.080 (3)	0.062 (2)	−0.024 (2)	0.001 (2)	−0.020 (2)
F7	0.057 (4)	0.069 (4)	0.126 (6)	0.013 (3)	0.020 (3)	−0.027 (5)
F8	0.072 (3)	0.086 (3)	0.056 (2)	−0.007 (3)	−0.0063 (18)	0.007 (3)
C14	0.047 (4)	0.083 (5)	0.056 (5)	−0.011 (4)	0.000 (4)	−0.006 (5)
F3'	0.080 (4)	0.053 (4)	0.118 (7)	−0.010 (3)	−0.005 (4)	−0.019 (4)
F4'	0.055 (3)	0.115 (5)	0.100 (4)	−0.021 (3)	0.016 (2)	0.026 (3)
F5'	0.069 (3)	0.122 (4)	0.160 (4)	0.026 (2)	0.052 (3)	0.015 (3)
F6'	0.085 (6)	0.116 (7)	0.119 (6)	−0.025 (4)	−0.053 (5)	0.001 (4)
F7'	0.055 (5)	0.083 (5)	0.162 (10)	0.007 (3)	−0.022 (6)	0.035 (4)
F8'	0.103 (4)	0.153 (6)	0.052 (3)	0.000 (4)	−0.005 (2)	−0.011 (4)
C14'	0.039 (5)	0.083 (5)	0.078 (6)	−0.004 (4)	−0.007 (4)	0.001 (5)
F9	0.1169 (17)	0.0768 (15)	0.219 (3)	0.0251 (13)	0.0284 (18)	0.0456 (16)
F10	0.0937 (15)	0.0882 (15)	0.199 (3)	−0.0390 (12)	0.0209 (15)	−0.0328 (16)
C1	0.0506 (16)	0.080 (2)	0.0600 (18)	0.0015 (15)	0.0059 (14)	0.0020 (16)
C2	0.0507 (17)	0.098 (3)	0.060 (2)	0.0127 (17)	0.0050 (15)	0.0160 (19)
C3	0.071 (2)	0.082 (2)	0.073 (2)	0.0186 (18)	0.0212 (18)	0.019 (2)
C4	0.086 (2)	0.067 (2)	0.069 (2)	0.0108 (18)	0.0164 (18)	0.0007 (18)
C5	0.0697 (19)	0.066 (2)	0.0552 (17)	0.0024 (16)	0.0059 (15)	0.0067 (16)
C6	0.0431 (14)	0.0633 (19)	0.0523 (16)	−0.0006 (13)	0.0098 (13)	0.0077 (14)
C7	0.0424 (14)	0.0629 (18)	0.0519 (16)	−0.0053 (12)	0.0078 (12)	0.0025 (13)
C8	0.0490 (15)	0.0525 (17)	0.0538 (16)	−0.0093 (12)	0.0038 (13)	0.0003 (13)
C9	0.0432 (14)	0.0529 (16)	0.0477 (15)	−0.0066 (12)	0.0051 (12)	0.0031 (13)
C10	0.0512 (15)	0.0576 (18)	0.0538 (16)	−0.0067 (13)	0.0080 (13)	0.0021 (14)
C11	0.082 (2)	0.062 (2)	0.0650 (19)	−0.0074 (16)	0.0051 (16)	−0.0089 (16)
C12	0.0420 (14)	0.0508 (16)	0.0509 (15)	−0.0035 (12)	0.0078 (12)	−0.0010 (13)
C13	0.0518 (17)	0.068 (2)	0.0642 (19)	−0.0150 (15)	0.0069 (15)	−0.0032 (17)
C15	0.0550 (17)	0.064 (2)	0.0602 (19)	0.0074 (15)	0.0035 (14)	−0.0007 (16)
C16	0.0427 (14)	0.0489 (16)	0.0476 (15)	0.0014 (11)	0.0067 (12)	−0.0053 (13)
C17	0.0500 (15)	0.0477 (16)	0.0474 (15)	0.0005 (12)	0.0107 (12)	0.0022 (12)
C18	0.0557 (17)	0.0496 (17)	0.0702 (18)	0.0027 (13)	0.0236 (14)	0.0007 (14)
C19	0.082 (2)	0.0526 (19)	0.140 (3)	0.0122 (16)	0.057 (2)	0.003 (2)
C20	0.0481 (15)	0.0495 (16)	0.0564 (16)	0.0054 (12)	0.0114 (12)	0.0025 (13)
C21	0.0550 (16)	0.0513 (17)	0.0523 (16)	−0.0027 (13)	0.0150 (13)	−0.0012 (13)
C22	0.0610 (17)	0.0527 (17)	0.0519 (16)	−0.0033 (14)	0.0208 (14)	−0.0033 (13)
C23	0.067 (2)	0.060 (2)	0.093 (2)	0.0005 (16)	0.0160 (17)	0.0110 (17)
C24	0.087 (3)	0.056 (2)	0.108 (3)	0.0137 (19)	0.029 (2)	0.0089 (19)
C25	0.111 (3)	0.0465 (19)	0.117 (3)	−0.008 (2)	0.050 (2)	−0.0113 (19)
C26	0.079 (2)	0.066 (2)	0.095 (2)	−0.0179 (19)	0.0298 (19)	−0.0237 (19)
C27	0.0635 (19)	0.0549 (18)	0.077 (2)	−0.0060 (14)	0.0152 (15)	−0.0056 (15)

Geometric parameters (Å, º)

S1—C10	1.720 (3)	C6—C7	1.469 (4)
S1—C7	1.729 (3)	C7—C8	1.363 (3)
S2—C18	1.711 (3)	C8—C9	1.421 (3)
S2—C21	1.725 (3)	C8—H8	0.9300
F1—C2	1.353 (3)	C9—C10	1.372 (3)
F2—C4	1.350 (4)	C9—C12	1.473 (3)
F3—C13	1.329 (7)	C10—C11	1.498 (4)
F4—C13	1.351 (5)	C11—H11A	0.9600
F5—C14	1.340 (8)	C11—H11B	0.9600
F6—C14	1.334 (7)	C11—H11C	0.9600
F7—C15	1.343 (7)	C12—C16	1.343 (3)
F8—C15	1.394 (5)	C12—C13	1.501 (4)
C14—C15	1.449 (9)	C15—C16	1.493 (4)
C14—C13	1.617 (9)	C16—C17	1.482 (3)
F3'—C13	1.358 (7)	C17—C18	1.371 (3)
F4'—C13	1.382 (5)	C17—C20	1.422 (3)
F5'—C14'	1.355 (7)	C18—C19	1.500 (4)
F6'—C14'	1.344 (8)	C19—H19A	0.9600
F7'—C15	1.325 (8)	C19—H19B	0.9600
F8'—C15	1.337 (5)	C19—H19C	0.9600
C14'—C13	1.434 (9)	C20—C21	1.356 (3)
C14'—C15	1.619 (9)	C20—H20	0.9300
F9—C24	1.361 (4)	C21—C22	1.470 (4)
F10—C26	1.352 (4)	C22—C23	1.386 (4)
C1—C2	1.371 (4)	C22—C27	1.390 (4)
C1—C6	1.396 (4)	C23—C24	1.373 (4)
C1—H1	0.9300	C23—H23	0.9300
C2—C3	1.360 (4)	C24—C25	1.360 (5)
C3—C4	1.360 (4)	C25—C26	1.354 (5)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.371 (4)	C26—C27	1.360 (4)
C5—C6	1.388 (4)	C27—H27	0.9300
C5—H5	0.9300
C10—S1—C7	93.40 (13)	C14'—C13—C12	107.1 (4)
C18—S2—C21	92.80 (13)	F3—C13—C14	109.3 (6)
F6—C14—F5	108.9 (7)	F4—C13—C14	105.2 (4)
F6—C14—C15	111.3 (5)	F3'—C13—C14	89.1 (5)
F5—C14—C15	114.1 (7)	F4'—C13—C14	137.6 (4)
F6—C14—C13	108.1 (6)	C14'—C13—C14	28.7 (3)
F5—C14—C13	111.4 (8)	C12—C13—C14	102.8 (3)
C15—C14—C13	102.9 (5)	F7'—C15—F8'	111.7 (7)
F6'—C14'—F5'	109.3 (7)	F7'—C15—F7	19.5 (12)
F6'—C14'—C13	114.4 (8)	F8'—C15—F7	125.8 (7)
F5'—C14'—C13	109.2 (6)	F7'—C15—F8	81.6 (7)
F6'—C14'—C15	111.1 (8)	F8'—C15—F8	36.2 (3)
F5'—C14'—C15	109.2 (6)	F7—C15—F8	99.9 (7)
C13—C14'—C15	103.5 (4)	F7'—C15—C14	127.0 (7)
C2—C1—C6	119.1 (3)	F8'—C15—C14	78.8 (4)
C2—C1—H1	120.4	F7—C15—C14	112.8 (7)
C6—C1—H1	120.4	F8—C15—C14	113.2 (4)
F1—C2—C3	118.5 (3)	F7'—C15—C16	114.4 (6)
F1—C2—C1	118.1 (3)	F8'—C15—C16	113.1 (3)
C3—C2—C1	123.4 (3)	F7—C15—C16	113.1 (6)
C2—C3—C4	116.4 (3)	F8—C15—C16	111.2 (3)
C2—C3—H3	121.8	C14—C15—C16	106.8 (4)
C4—C3—H3	121.8	F7'—C15—C14'	107.7 (7)
F2—C4—C3	118.1 (3)	F8'—C15—C14'	106.2 (4)
F2—C4—C5	118.5 (3)	F7—C15—C14'	89.7 (7)
C3—C4—C5	123.3 (3)	F8—C15—C14'	137.0 (4)
C4—C5—C6	119.4 (3)	C14—C15—C14'	28.6 (3)
C4—C5—H5	120.3	C16—C15—C14'	102.9 (3)
C6—C5—H5	120.3	C12—C16—C17	130.2 (2)
C5—C6—C1	118.2 (3)	C12—C16—C15	110.7 (2)
C5—C6—C7	120.7 (2)	C17—C16—C15	119.0 (2)
C1—C6—C7	121.0 (3)	C18—C17—C20	112.4 (2)
C8—C7—C6	129.5 (2)	C18—C17—C16	123.5 (2)
C8—C7—S1	109.5 (2)	C20—C17—C16	124.1 (2)
C6—C7—S1	121.00 (19)	C17—C18—C19	129.3 (2)
C7—C8—C9	114.2 (2)	C17—C18—S2	110.8 (2)
C7—C8—H8	122.9	C19—C18—S2	119.8 (2)
C9—C8—H8	122.9	C18—C19—H19A	109.5
C10—C9—C8	112.7 (2)	C18—C19—H19B	109.5
C10—C9—C12	123.3 (2)	H19A—C19—H19B	109.5
C8—C9—C12	124.0 (2)	C18—C19—H19C	109.5
C9—C10—C11	130.3 (2)	H19A—C19—H19C	109.5
C9—C10—S1	110.2 (2)	H19B—C19—H19C	109.5
C11—C10—S1	119.5 (2)	C21—C20—C17	113.7 (2)
C10—C11—H11A	109.5	C21—C20—H20	123.2
C10—C11—H11B	109.5	C17—C20—H20	123.2
H11A—C11—H11B	109.5	C20—C21—C22	129.4 (2)
C10—C11—H11C	109.5	C20—C21—S2	110.3 (2)
H11A—C11—H11C	109.5	C22—C21—S2	120.25 (19)
H11B—C11—H11C	109.5	C23—C22—C27	118.7 (3)
C16—C12—C9	129.1 (2)	C23—C22—C21	120.3 (3)
C16—C12—C13	110.4 (2)	C27—C22—C21	121.0 (3)
C9—C12—C13	120.5 (2)	C24—C23—C22	118.6 (3)
F3—C13—F4	109.6 (6)	C24—C23—H23	120.7
F3—C13—F3'	25.4 (6)	C22—C23—H23	120.7
F4—C13—F3'	131.8 (6)	C25—C24—F9	118.4 (3)
F3—C13—F4'	76.2 (5)	C25—C24—C23	123.5 (3)
F4—C13—F4'	39.4 (3)	F9—C24—C23	118.1 (3)
F3'—C13—F4'	101.5 (5)	C26—C25—C24	116.7 (3)
F3—C13—C14'	126.6 (7)	C26—C25—H25	121.7
F4—C13—C14'	77.5 (4)	C24—C25—H25	121.7
F3'—C13—C14'	113.2 (6)	F10—C26—C25	117.6 (3)
F4'—C13—C14'	114.1 (4)	F10—C26—C27	119.2 (3)
F3—C13—C12	117.2 (6)	C25—C26—C27	123.2 (3)
F4—C13—C12	111.8 (3)	C26—C27—C22	119.5 (3)
F3'—C13—C12	109.2 (5)	C26—C27—H27	120.3
F4'—C13—C12	111.8 (3)	C22—C27—H27	120.3
C6—C1—C2—F1	179.3 (2)	C13—C14—C15—F7'	115.2 (9)
C6—C1—C2—C3	0.1 (4)	F6—C14—C15—F8'	−20.4 (6)
F1—C2—C3—C4	−179.7 (3)	F5—C14—C15—F8'	103.3 (8)
C1—C2—C3—C4	−0.5 (5)	C13—C14—C15—F8'	−135.9 (5)
C2—C3—C4—F2	−179.0 (3)	F6—C14—C15—F7	−144.7 (8)
C2—C3—C4—C5	0.0 (5)	F5—C14—C15—F7	−20.9 (11)
F2—C4—C5—C6	179.9 (3)	C13—C14—C15—F7	99.8 (8)
C3—C4—C5—C6	0.9 (5)	F6—C14—C15—F8	−32.1 (7)
C4—C5—C6—C1	−1.3 (4)	F5—C14—C15—F8	91.6 (8)
C4—C5—C6—C7	178.7 (3)	C13—C14—C15—F8	−147.7 (4)
C2—C1—C6—C5	0.9 (4)	F6—C14—C15—C16	90.5 (6)
C2—C1—C6—C7	−179.2 (2)	F5—C14—C15—C16	−145.7 (7)
C5—C6—C7—C8	−15.8 (4)	C13—C14—C15—C16	−25.0 (4)
C1—C6—C7—C8	164.2 (3)	F6—C14—C15—C14'	176.7 (15)
C5—C6—C7—S1	164.8 (2)	F5—C14—C15—C14'	−59.6 (11)
C1—C6—C7—S1	−15.2 (3)	C13—C14—C15—C14'	61.1 (9)
C10—S1—C7—C8	0.6 (2)	F6'—C14'—C15—F7'	−95.9 (10)
C10—S1—C7—C6	−179.9 (2)	F5'—C14'—C15—F7'	24.7 (8)
C6—C7—C8—C9	179.3 (2)	C13—C14'—C15—F7'	140.9 (7)
S1—C7—C8—C9	−1.3 (3)	F6'—C14'—C15—F8'	23.9 (8)
C7—C8—C9—C10	1.5 (3)	F5'—C14'—C15—F8'	144.5 (5)
C7—C8—C9—C12	−179.7 (2)	C13—C14'—C15—F8'	−99.3 (5)
C8—C9—C10—C11	177.3 (3)	F6'—C14'—C15—F7	−103.5 (9)
C12—C9—C10—C11	−1.4 (4)	F5'—C14'—C15—F7	17.1 (8)
C8—C9—C10—S1	−1.0 (3)	C13—C14'—C15—F7	133.4 (7)
C12—C9—C10—S1	−179.74 (19)	F6'—C14'—C15—F8	0.8 (11)
C7—S1—C10—C9	0.2 (2)	F5'—C14'—C15—F8	121.4 (6)
C7—S1—C10—C11	−178.3 (2)	C13—C14'—C15—F8	−122.3 (6)
C10—C9—C12—C16	−46.3 (4)	F6'—C14'—C15—C14	41.3 (10)
C8—C9—C12—C16	135.1 (3)	F5'—C14'—C15—C14	161.9 (14)
C10—C9—C12—C13	132.6 (3)	C13—C14'—C15—C14	−81.8 (11)
C8—C9—C12—C13	−46.0 (4)	F6'—C14'—C15—C16	142.9 (7)
F6'—C14'—C13—F3	1.4 (12)	F5'—C14'—C15—C16	−96.5 (5)
F5'—C14'—C13—F3	−121.4 (7)	C13—C14'—C15—C16	19.7 (5)
C15—C14'—C13—F3	122.3 (7)	C9—C12—C16—C17	−9.7 (5)
F6'—C14'—C13—F4	106.6 (9)	C13—C12—C16—C17	171.3 (2)
F5'—C14'—C13—F4	−16.2 (5)	C9—C12—C16—C15	173.5 (2)
C15—C14'—C13—F4	−132.4 (5)	C13—C12—C16—C15	−5.5 (3)
F6'—C14'—C13—F3'	−23.7 (11)	F7'—C15—C16—C12	−125.1 (7)
F5'—C14'—C13—F3'	−146.5 (6)	F8'—C15—C16—C12	105.4 (4)
C15—C14'—C13—F3'	97.3 (6)	F7—C15—C16—C12	−103.9 (7)
F6'—C14'—C13—F4'	91.7 (9)	F8—C15—C16—C12	144.6 (3)
F5'—C14'—C13—F4'	−31.1 (7)	C14—C15—C16—C12	20.7 (4)
C15—C14'—C13—F4'	−147.3 (4)	C14'—C15—C16—C12	−8.6 (4)
F6'—C14'—C13—C12	−144.1 (8)	F7'—C15—C16—C17	57.6 (8)
F5'—C14'—C13—C12	93.1 (6)	F8'—C15—C16—C17	−71.8 (4)
C15—C14'—C13—C12	−23.1 (5)	F7—C15—C16—C17	78.9 (7)
F6'—C14'—C13—C14	−58.6 (11)	F8—C15—C16—C17	−32.6 (4)
F5'—C14'—C13—C14	178.6 (15)	C14—C15—C16—C17	−156.5 (3)
C15—C14'—C13—C14	62.4 (10)	C14'—C15—C16—C17	174.1 (3)
C16—C12—C13—F3	−129.8 (5)	C12—C16—C17—C18	−44.7 (4)
C9—C12—C13—F3	51.1 (6)	C15—C16—C17—C18	132.0 (3)
C16—C12—C13—F4	102.5 (4)	C12—C16—C17—C20	137.8 (3)
C9—C12—C13—F4	−76.6 (4)	C15—C16—C17—C20	−45.6 (3)
C16—C12—C13—F3'	−103.4 (5)	C20—C17—C18—C19	176.9 (3)
C9—C12—C13—F3'	77.4 (5)	C16—C17—C18—C19	−0.9 (5)
C16—C12—C13—F4'	145.0 (4)	C20—C17—C18—S2	−0.4 (3)
C9—C12—C13—F4'	−34.1 (5)	C16—C17—C18—S2	−178.24 (19)
C16—C12—C13—C14'	19.4 (4)	C21—S2—C18—C17	−0.3 (2)
C9—C12—C13—C14'	−159.7 (4)	C21—S2—C18—C19	−177.8 (3)
C16—C12—C13—C14	−9.9 (4)	C18—C17—C20—C21	1.1 (3)
C9—C12—C13—C14	171.0 (3)	C16—C17—C20—C21	178.9 (2)
F6—C14—C13—F3	28.8 (8)	C17—C20—C21—C22	177.4 (2)
F5—C14—C13—F3	−90.8 (9)	C17—C20—C21—S2	−1.3 (3)
C15—C14—C13—F3	146.7 (6)	C18—S2—C21—C20	0.9 (2)
F6—C14—C13—F4	146.5 (5)	C18—S2—C21—C22	−178.0 (2)
F5—C14—C13—F4	26.9 (8)	C20—C21—C22—C23	25.2 (4)
C15—C14—C13—F4	−95.7 (5)	S2—C21—C22—C23	−156.1 (2)
F6—C14—C13—F3'	13.2 (7)	C20—C21—C22—C27	−154.3 (3)
F5—C14—C13—F3'	−106.4 (8)	S2—C21—C22—C27	24.3 (3)
C15—C14—C13—F3'	131.0 (6)	C27—C22—C23—C24	−0.3 (4)
F6—C14—C13—F4'	119.3 (6)	C21—C22—C23—C24	−179.8 (3)
F5—C14—C13—F4'	−0.3 (11)	C22—C23—C24—C25	−0.2 (5)
C15—C14—C13—F4'	−122.8 (6)	C22—C23—C24—F9	179.9 (3)
F6—C14—C13—C14'	161.4 (15)	F9—C24—C25—C26	−180.0 (3)
F5—C14—C13—C14'	41.8 (10)	C23—C24—C25—C26	0.1 (6)
C15—C14—C13—C14'	−80.7 (11)	C24—C25—C26—F10	−179.8 (3)
F6—C14—C13—C12	−96.3 (5)	C24—C25—C26—C27	0.5 (5)
F5—C14—C13—C12	144.1 (7)	F10—C26—C27—C22	179.3 (3)
C15—C14—C13—C12	21.5 (5)	C25—C26—C27—C22	−1.0 (5)
F6—C14—C15—F7'	−129.2 (9)	C23—C22—C27—C26	0.9 (4)
F5—C14—C15—F7'	−5.5 (12)	C21—C22—C27—C26	−179.6 (3)