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

The title compound, C₂₂H₁₅ClF₆S₂, is a new unsymmetrical photochromic diaryl­ethene with a para-chloro­phenyl substituent. It is a promising candidate for an optical recording medium and other optoelectronic device materials. The distance between the two reactive C atoms is 3.612 (6) Å; the dihedral angles between the cyclo­pentene ring and the thio­phene rings are 40.9 (5) and 41.2 (5)°, and that between one thio­phene ring and the adjacent benzene ring is 27.8 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.114
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT301_ALERT_3_C Main Residue  Disorder .........................      16.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  F6'     ..       3.11 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.40 Deg.
              F2'  -C19  -F2      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.90 Deg.
              F1   -C19  -F1'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      38.10 Deg.
              F3'  -C20  -F3      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.90 Deg.
              F4   -C20  -F4'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.00 Deg.
              F6'  -C21  -F6      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.20 Deg.
              F5   -C21  -F5'     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 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
   9 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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-[5-(4-Chlorophenyl)-2-methyl-3-thienyl]-2-(2,5-dimethyl-3-thienyl)- 3,3,4,4,5,5-hexafluorocyclopent-1-ene

Crystal data

C22H15ClF6S2	Dx = 1.537 Mg m^−3
Mr = 492.91	Melting point: 418 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.232 (3) Å	Cell parameters from 3265 reflections
b = 9.0912 (13) Å	θ = 2.9–24.2°
c = 11.1534 (17) Å	µ = 0.43 mm^−1
β = 98.243 (2)°	T = 294 K
V = 2130.6 (5) Å^3	Prism, colorless
Z = 4	0.24 × 0.22 × 0.20 mm
F(000) = 1000

Data collection

Bruker SMART CCD area-detector diffractometer	4337 independent reflections
Radiation source: fine-focus sealed tube	2721 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 26.4°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→26
Tmin = 0.903, Tmax = 0.918	k = −5→11
11640 measured reflections	l = −13→13

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) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.3854P] where P = (Fo^2 + 2Fc^2)/3
4337 reflections	(Δ/σ)max = 0.001
340 parameters	Δρmax = 0.21 e Å^−3
24 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. 1H NMR (400 MHz, CDCl3): δ 1.86 (s, 3H, –CH3), 1.92 (s, 3H, –CH3), 2.42 (s, 3H, –CH3), 6.73 (s, 1H, thiophene-H), 7.23 (s, 1H, thiophene-H), 7.34–7.36 (d, 2H, J = 8.5?Hz, ben-H), 7.45–7.47 (d, 2H, J = 8.5 Hz, ben-H); 19 F NMR (400 MHz, CDCl3): δ 109.88 (2 F), 110.19 (2 F), 131.87 (2 F). 13 C NMR (400 MHz, CDCl3): δ 14.3, 14.5, 15.1, 122.9, 124.5, 126.2, 126.8, 129.2, 131.9, 133.7, 137.9, 139.8, 140.7, 141.5.

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)
S1	0.06754 (3)	0.29044 (8)	0.52882 (6)	0.0626 (2)
S2	0.35808 (3)	0.31480 (7)	0.55798 (6)	0.0579 (2)
Cl1	0.59112 (3)	0.38894 (10)	0.16552 (8)	0.0858 (3)
F1	0.1258 (5)	0.8341 (7)	0.6560 (11)	0.076 (2)	0.63 (2)
F2	0.1049 (3)	0.8307 (5)	0.4626 (11)	0.080 (2)	0.63 (2)
F1'	0.1505 (8)	0.8150 (13)	0.7013 (11)	0.068 (3)	0.37 (2)
F2'	0.0939 (4)	0.8226 (10)	0.528 (2)	0.076 (3)	0.37 (2)
F3	0.2343 (3)	0.9495 (14)	0.6609 (8)	0.076 (2)	0.64 (3)
F4	0.1932 (5)	1.0241 (6)	0.4837 (13)	0.082 (3)	0.64 (3)
F3'	0.2138 (12)	1.012 (2)	0.609 (3)	0.101 (7)	0.36 (3)
F4'	0.1738 (7)	0.963 (3)	0.4276 (18)	0.098 (6)	0.36 (3)
F5	0.3154 (2)	0.8412 (5)	0.5422 (10)	0.0649 (18)	0.69 (3)
F6	0.2516 (4)	0.8257 (9)	0.3761 (6)	0.0657 (15)	0.69 (3)
F5'	0.3047 (14)	0.8355 (12)	0.609 (5)	0.116 (11)	0.31 (3)
F6'	0.2768 (19)	0.842 (2)	0.418 (4)	0.106 (10)	0.31 (3)
C1	0.00275 (13)	0.3640 (4)	0.7234 (3)	0.0767 (9)
H1A	0.0065	0.4283	0.7923	0.115*
H1B	0.0079	0.2639	0.7504	0.115*
H1C	−0.0385	0.3760	0.6763	0.115*
C2	0.05326 (10)	0.4012 (3)	0.6468 (2)	0.0543 (7)
C3	0.09182 (10)	0.5186 (3)	0.6545 (2)	0.0492 (6)
H3	0.0913	0.5911	0.7132	0.059*
C4	0.13368 (10)	0.5234 (3)	0.5652 (2)	0.0417 (5)
C5	0.12560 (10)	0.4047 (3)	0.4888 (2)	0.0474 (6)
C6	0.15693 (13)	0.3687 (3)	0.3809 (2)	0.0638 (7)
H6A	0.1701	0.4580	0.3458	0.096*
H6B	0.1274	0.3174	0.3222	0.096*
H6C	0.1934	0.3076	0.4052	0.096*
C7	0.26361 (13)	0.3698 (3)	0.7000 (2)	0.0608 (7)
H7A	0.2478	0.4552	0.7366	0.091*
H7B	0.2942	0.3207	0.7582	0.091*
H7C	0.2290	0.3042	0.6736	0.091*
C8	0.29459 (10)	0.4155 (3)	0.5934 (2)	0.0470 (6)
C9	0.28314 (9)	0.5337 (2)	0.5169 (2)	0.0381 (5)
C10	0.32624 (9)	0.5390 (2)	0.4305 (2)	0.0408 (5)
H10	0.3245	0.6119	0.3716	0.049*
C11	0.36982 (10)	0.4300 (3)	0.4404 (2)	0.0440 (6)
C12	0.42332 (10)	0.4109 (3)	0.3715 (2)	0.0449 (6)
C13	0.41996 (11)	0.4683 (3)	0.2558 (2)	0.0546 (7)
H13	0.3824	0.5127	0.2202	0.066*
C14	0.47107 (12)	0.4614 (3)	0.1918 (2)	0.0596 (7)
H14	0.4680	0.5002	0.1141	0.072*
C15	0.52625 (11)	0.3963 (3)	0.2450 (3)	0.0561 (7)
C16	0.53145 (11)	0.3370 (3)	0.3583 (3)	0.0630 (7)
H16	0.5692	0.2924	0.3927	0.076*
C17	0.47980 (11)	0.3438 (3)	0.4218 (2)	0.0576 (7)
H17	0.4831	0.3030	0.4989	0.069*
C18	0.17644 (10)	0.6471 (2)	0.55328 (19)	0.0388 (5)
C19	0.15227 (11)	0.8008 (3)	0.5657 (2)	0.0550 (7)
C20	0.20533 (12)	0.9030 (3)	0.5443 (3)	0.0564 (7)
C21	0.25575 (11)	0.8050 (3)	0.5034 (3)	0.0531 (6)
C22	0.23643 (10)	0.6505 (2)	0.52638 (19)	0.0378 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0583 (4)	0.0657 (5)	0.0644 (5)	−0.0233 (3)	0.0112 (3)	0.0029 (4)
S2	0.0576 (4)	0.0512 (4)	0.0683 (5)	0.0187 (3)	0.0209 (3)	0.0120 (3)
Cl1	0.0561 (4)	0.1090 (7)	0.1011 (6)	0.0012 (4)	0.0410 (4)	−0.0214 (5)
F1	0.081 (4)	0.063 (2)	0.097 (5)	0.005 (2)	0.059 (4)	−0.013 (3)
F2	0.059 (2)	0.069 (2)	0.105 (5)	0.0173 (17)	−0.012 (3)	0.006 (2)
F1'	0.091 (6)	0.059 (4)	0.059 (5)	0.000 (4)	0.028 (4)	−0.018 (3)
F2'	0.047 (3)	0.066 (3)	0.115 (9)	0.017 (2)	0.005 (4)	−0.004 (4)
F3	0.069 (2)	0.077 (4)	0.084 (3)	−0.006 (2)	0.016 (2)	−0.038 (3)
F4	0.083 (3)	0.048 (3)	0.123 (6)	0.021 (2)	0.044 (4)	0.022 (3)
F3'	0.112 (10)	0.067 (7)	0.134 (13)	−0.027 (7)	0.056 (10)	−0.043 (9)
F4'	0.082 (5)	0.118 (13)	0.097 (8)	0.036 (7)	0.024 (5)	0.049 (8)
F5	0.0425 (16)	0.0514 (17)	0.103 (4)	−0.0089 (13)	0.016 (2)	−0.005 (2)
F6	0.088 (4)	0.057 (2)	0.058 (3)	0.006 (2)	0.030 (2)	0.0122 (15)
F5'	0.082 (10)	0.066 (5)	0.18 (2)	−0.024 (5)	−0.064 (13)	−0.003 (7)
F6'	0.118 (18)	0.055 (6)	0.17 (2)	0.018 (9)	0.113 (17)	0.038 (11)
C1	0.0528 (16)	0.105 (2)	0.076 (2)	−0.0139 (16)	0.0223 (14)	0.0232 (18)
C2	0.0380 (12)	0.0710 (18)	0.0544 (16)	−0.0060 (13)	0.0090 (11)	0.0136 (14)
C3	0.0390 (12)	0.0613 (16)	0.0496 (15)	0.0044 (12)	0.0146 (11)	0.0021 (12)
C4	0.0340 (11)	0.0470 (14)	0.0457 (14)	0.0017 (10)	0.0116 (10)	0.0021 (11)
C5	0.0439 (13)	0.0503 (15)	0.0493 (15)	−0.0075 (11)	0.0114 (11)	0.0026 (12)
C6	0.0718 (17)	0.0647 (17)	0.0586 (17)	−0.0149 (14)	0.0224 (14)	−0.0167 (14)
C7	0.0651 (16)	0.0602 (17)	0.0612 (17)	0.0094 (14)	0.0228 (13)	0.0158 (14)
C8	0.0442 (12)	0.0458 (14)	0.0529 (15)	0.0026 (11)	0.0138 (11)	0.0014 (12)
C9	0.0330 (11)	0.0373 (12)	0.0450 (13)	−0.0001 (9)	0.0086 (9)	−0.0013 (10)
C10	0.0355 (11)	0.0405 (13)	0.0479 (14)	0.0014 (10)	0.0103 (10)	0.0028 (10)
C11	0.0396 (12)	0.0431 (13)	0.0503 (15)	0.0031 (10)	0.0102 (10)	−0.0022 (11)
C12	0.0380 (12)	0.0427 (13)	0.0553 (15)	0.0044 (10)	0.0113 (11)	−0.0088 (11)
C13	0.0445 (13)	0.0622 (16)	0.0587 (17)	0.0144 (12)	0.0128 (12)	−0.0010 (13)
C14	0.0576 (15)	0.0648 (17)	0.0600 (17)	0.0101 (14)	0.0199 (13)	−0.0033 (14)
C15	0.0430 (14)	0.0566 (16)	0.0724 (19)	−0.0013 (12)	0.0206 (13)	−0.0167 (14)
C16	0.0392 (13)	0.0746 (19)	0.075 (2)	0.0163 (13)	0.0085 (13)	−0.0092 (16)
C17	0.0494 (14)	0.0614 (17)	0.0634 (17)	0.0155 (13)	0.0128 (12)	0.0012 (13)
C18	0.0371 (11)	0.0422 (13)	0.0384 (13)	0.0024 (10)	0.0096 (9)	−0.0026 (10)
C19	0.0394 (13)	0.0533 (16)	0.0749 (19)	0.0070 (12)	0.0166 (13)	−0.0105 (14)
C20	0.0638 (16)	0.0377 (15)	0.0716 (19)	0.0037 (13)	0.0227 (14)	−0.0039 (15)
C21	0.0389 (13)	0.0444 (14)	0.078 (2)	−0.0027 (11)	0.0137 (14)	0.0027 (14)
C22	0.0368 (11)	0.0385 (12)	0.0389 (13)	0.0004 (10)	0.0087 (9)	−0.0007 (10)

Geometric parameters (Å, º)

S1—C2	1.718 (3)	C6—H6B	0.9600
S1—C5	1.719 (2)	C6—H6C	0.9600
S2—C8	1.722 (2)	C7—C8	1.498 (3)
S2—C11	1.724 (2)	C7—H7A	0.9600
Cl1—C15	1.743 (2)	C7—H7B	0.9600
F1—C19	1.258 (7)	C7—H7C	0.9600
F2—C19	1.441 (7)	C8—C9	1.372 (3)
F1'—C19	1.523 (11)	C9—C10	1.422 (3)
F2'—C19	1.266 (8)	C9—C22	1.467 (3)
F3—C20	1.420 (7)	C10—C11	1.349 (3)
F4—C20	1.298 (6)	C10—H10	0.9300
F3'—C20	1.226 (8)	C11—C12	1.470 (3)
F4'—C20	1.478 (12)	C12—C13	1.384 (3)
F5—C21	1.320 (6)	C12—C17	1.390 (3)
F6—C21	1.422 (8)	C13—C14	1.383 (3)
F5'—C21	1.48 (2)	C13—H13	0.9300
F6'—C21	1.16 (2)	C14—C15	1.369 (4)
C1—C2	1.502 (3)	C14—H14	0.9300
C1—H1A	0.9600	C15—C16	1.363 (4)
C1—H1B	0.9600	C16—C17	1.389 (3)
C1—H1C	0.9600	C16—H16	0.9300
C2—C3	1.341 (3)	C17—H17	0.9300
C3—C4	1.428 (3)	C18—C22	1.350 (3)
C3—H3	0.9300	C18—C19	1.502 (3)
C4—C5	1.371 (3)	C19—C20	1.506 (3)
C4—C18	1.464 (3)	C20—C21	1.512 (3)
C5—C6	1.492 (3)	C21—C22	1.496 (3)
C6—H6A	0.9600
C2—S1—C5	93.27 (12)	C15—C16—H16	120.3
C8—S2—C11	93.15 (11)	C17—C16—H16	120.3
C2—C1—H1A	109.5	C16—C17—C12	120.8 (3)
C2—C1—H1B	109.5	C16—C17—H17	119.6
H1A—C1—H1B	109.5	C12—C17—H17	119.6
C2—C1—H1C	109.5	C22—C18—C4	130.9 (2)
H1A—C1—H1C	109.5	C22—C18—C19	110.20 (19)
H1B—C1—H1C	109.5	C4—C18—C19	118.82 (18)
C3—C2—C1	128.5 (3)	F1—C19—F2'	72.8 (5)
C3—C2—S1	110.02 (18)	F1—C19—F2	104.6 (3)
C1—C2—S1	121.5 (2)	F2'—C19—F2	33.4 (6)
C2—C3—C4	114.5 (2)	F1—C19—C18	119.7 (4)
C2—C3—H3	122.7	F2'—C19—C18	116.4 (4)
C4—C3—H3	122.7	F2—C19—C18	108.1 (3)
C5—C4—C3	112.0 (2)	F1—C19—C20	114.1 (4)
C5—C4—C18	124.94 (19)	F2'—C19—C20	124.6 (8)
C3—C4—C18	122.9 (2)	F2—C19—C20	102.1 (5)
C4—C5—C6	130.0 (2)	C18—C19—C20	106.62 (19)
C4—C5—S1	110.15 (17)	F1—C19—F1'	26.9 (3)
C6—C5—S1	119.76 (18)	F2'—C19—F1'	99.1 (6)
C5—C6—H6A	109.5	F2—C19—F1'	131.5 (4)
C5—C6—H6B	109.5	C18—C19—F1'	103.2 (6)
H6A—C6—H6B	109.5	C20—C19—F1'	103.3 (5)
C5—C6—H6C	109.5	F3'—C20—F4	67.7 (11)
H6A—C6—H6C	109.5	F3'—C20—F3	38.1 (12)
H6B—C6—H6C	109.5	F4—C20—F3	104.6 (3)
C8—C7—H7A	109.5	F3'—C20—F4'	103.4 (7)
C8—C7—H7B	109.5	F4—C20—F4'	36.9 (7)
H7A—C7—H7B	109.5	F3—C20—F4'	141.2 (9)
C8—C7—H7C	109.5	F3'—C20—C19	117.1 (4)
H7A—C7—H7C	109.5	F4—C20—C19	120.6 (5)
H7B—C7—H7C	109.5	F3—C20—C19	105.9 (4)
C9—C8—C7	130.7 (2)	F4'—C20—C19	96.4 (10)
C9—C8—S2	110.39 (17)	F3'—C20—C21	127.2 (12)
C7—C8—S2	118.82 (18)	F4—C20—C21	116.0 (3)
C8—C9—C10	111.96 (19)	F3—C20—C21	102.7 (4)
C8—C9—C22	125.7 (2)	F4'—C20—C21	101.6 (8)
C10—C9—C22	122.16 (19)	C19—C20—C21	105.2 (2)
C11—C10—C9	114.8 (2)	F6'—C21—F5	75 (2)
C11—C10—H10	122.6	F6'—C21—F6	28 (2)
C9—C10—H10	122.6	F5—C21—F6	102.3 (4)
C10—C11—C12	128.0 (2)	F6'—C21—F5'	107.1 (10)
C10—C11—S2	109.66 (16)	F5—C21—F5'	33.2 (19)
C12—C11—S2	122.19 (17)	F6—C21—F5'	134.9 (19)
C13—C12—C17	117.9 (2)	F6'—C21—C22	123.9 (16)
C13—C12—C11	120.2 (2)	F5—C21—C22	116.9 (4)
C17—C12—C11	121.8 (2)	F6—C21—C22	108.4 (4)
C14—C13—C12	121.6 (2)	F5'—C21—C22	102.5 (10)
C14—C13—H13	119.2	F6'—C21—C20	116.9 (10)
C12—C13—H13	119.2	F5—C21—C20	116.2 (3)
C15—C14—C13	118.8 (3)	F6—C21—C20	106.2 (4)
C15—C14—H14	120.6	F5'—C21—C20	95.5 (17)
C13—C14—H14	120.6	C22—C21—C20	106.2 (2)
C16—C15—C14	121.5 (2)	C18—C22—C9	132.0 (2)
C16—C15—Cl1	119.4 (2)	C18—C22—C21	110.48 (19)
C14—C15—Cl1	119.0 (2)	C9—C22—C21	117.55 (18)
C15—C16—C17	119.3 (2)
C5—S1—C2—C3	−0.5 (2)	C18—C19—C20—F4	140.9 (7)
C5—S1—C2—C1	178.2 (2)	F1'—C19—C20—F4	−110.7 (10)
C1—C2—C3—C4	−178.3 (2)	F1—C19—C20—F3	33.6 (9)
S1—C2—C3—C4	0.4 (3)	F2'—C19—C20—F3	118.7 (12)
C2—C3—C4—C5	0.0 (3)	F2—C19—C20—F3	145.8 (7)
C2—C3—C4—C18	175.9 (2)	C18—C19—C20—F3	−100.9 (5)
C3—C4—C5—C6	177.2 (2)	F1'—C19—C20—F3	7.5 (9)
C18—C4—C5—C6	1.4 (4)	F1—C19—C20—F4'	−114.3 (13)
C3—C4—C5—S1	−0.4 (3)	F2'—C19—C20—F4'	−29.2 (15)
C18—C4—C5—S1	−176.15 (18)	F2—C19—C20—F4'	−2.0 (11)
C2—S1—C5—C4	0.50 (19)	C18—C19—C20—F4'	111.3 (11)
C2—S1—C5—C6	−177.4 (2)	F1'—C19—C20—F4'	−140.4 (12)
C11—S2—C8—C9	−0.02 (19)	F1—C19—C20—C21	141.8 (7)
C11—S2—C8—C7	−177.2 (2)	F2'—C19—C20—C21	−133.1 (11)
C7—C8—C9—C10	177.1 (2)	F2—C19—C20—C21	−105.9 (5)
S2—C8—C9—C10	0.4 (2)	C18—C19—C20—C21	7.4 (3)
C7—C8—C9—C22	2.2 (4)	F1'—C19—C20—C21	115.8 (7)
S2—C8—C9—C22	−174.46 (17)	F3'—C20—C21—F6'	−85 (3)
C8—C9—C10—C11	−0.6 (3)	F4—C20—C21—F6'	−4 (3)
C22—C9—C10—C11	174.4 (2)	F3—C20—C21—F6'	−118 (3)
C9—C10—C11—C12	−175.1 (2)	F4'—C20—C21—F6'	32 (3)
C9—C10—C11—S2	0.6 (2)	C19—C20—C21—F6'	132 (3)
C8—S2—C11—C10	−0.33 (18)	F3'—C20—C21—F5	0.2 (19)
C8—S2—C11—C12	175.6 (2)	F4—C20—C21—F5	81.1 (10)
C10—C11—C12—C13	−27.2 (4)	F3—C20—C21—F5	−32.3 (8)
S2—C11—C12—C13	157.63 (19)	F4'—C20—C21—F5	117.1 (14)
C10—C11—C12—C17	148.8 (2)	C19—C20—C21—F5	−142.9 (5)
S2—C11—C12—C17	−26.4 (3)	F3'—C20—C21—F6	−112.7 (18)
C17—C12—C13—C14	−0.7 (4)	F4—C20—C21—F6	−31.9 (9)
C11—C12—C13—C14	175.4 (2)	F3—C20—C21—F6	−145.2 (6)
C12—C13—C14—C15	−0.2 (4)	F4'—C20—C21—F6	4.2 (13)
C13—C14—C15—C16	0.8 (4)	C19—C20—C21—F6	104.2 (4)
C13—C14—C15—Cl1	−179.3 (2)	F3'—C20—C21—F5'	27 (2)
C14—C15—C16—C17	−0.6 (4)	F4—C20—C21—F5'	108.2 (18)
Cl1—C15—C16—C17	179.6 (2)	F3—C20—C21—F5'	−5.2 (16)
C15—C16—C17—C12	−0.4 (4)	F4'—C20—C21—F5'	144 (2)
C13—C12—C17—C16	1.0 (4)	C19—C20—C21—F5'	−115.8 (16)
C11—C12—C17—C16	−175.0 (2)	F3'—C20—C21—C22	132.1 (18)
C5—C4—C18—C22	−42.4 (4)	F4—C20—C21—C22	−147.1 (8)
C3—C4—C18—C22	142.2 (2)	F3—C20—C21—C22	99.5 (5)
C5—C4—C18—C19	134.1 (2)	F4'—C20—C21—C22	−111.1 (13)
C3—C4—C18—C19	−41.2 (3)	C19—C20—C21—C22	−11.1 (3)
C22—C18—C19—F1	−132.0 (7)	C4—C18—C22—C9	−10.2 (4)
C4—C18—C19—F1	50.8 (7)	C19—C18—C22—C9	173.0 (2)
C22—C18—C19—F2'	143.6 (12)	C4—C18—C22—C21	170.0 (2)
C4—C18—C19—F2'	−33.6 (12)	C19—C18—C22—C21	−6.8 (3)
C22—C18—C19—F2	108.6 (6)	C8—C9—C22—C18	−40.8 (4)
C4—C18—C19—F2	−68.6 (6)	C10—C9—C22—C18	144.9 (2)
C22—C18—C19—C20	−0.6 (3)	C8—C9—C22—C21	139.0 (2)
C4—C18—C19—C20	−177.8 (2)	C10—C9—C22—C21	−35.3 (3)
C22—C18—C19—F1'	−109.0 (6)	F6'—C21—C22—C18	−128 (3)
C4—C18—C19—F1'	73.8 (6)	F5—C21—C22—C18	142.9 (5)
F1—C19—C20—F3'	−6 (2)	F6—C21—C22—C18	−102.3 (4)
F2'—C19—C20—F3'	79 (2)	F5'—C21—C22—C18	111 (2)
F2—C19—C20—F3'	107 (2)	C20—C21—C22—C18	11.4 (3)
C18—C19—C20—F3'	−140 (2)	F6'—C21—C22—C9	52 (3)
F1'—C19—C20—F3'	−32 (2)	F5—C21—C22—C9	−37.0 (5)
F1—C19—C20—F4	−84.7 (10)	F6—C21—C22—C9	77.8 (5)
F2'—C19—C20—F4	0.4 (13)	F5'—C21—C22—C9	−69 (2)
F2—C19—C20—F4	27.6 (8)	C20—C21—C22—C9	−168.5 (2)