1,2-Bis[5-(2,4-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. There are two independent mol­ecules in the asymmetric unit. Both adopt a photoactive anti­parallel conformation. The distances between the reactive C atoms in the two mol­ecules are 3.664 (7) and 3.621 (7) Å. For one mol­ecule, the dihedral angles between the central cyclo­pentene ring and the thio­phene rings are 46.4 (9) and 51.9 (9)°, and those between the thio­phene rings and the adjacent benzene rings are 2.1 (8) and 18.9 (8)°. For the other mol­ecule, the dihedral angles between the central cyclo­pentene ring and the thio­phene rings are 134.5 (9) and 44.3 (9)°, and those between the thio­phene rings and the adjacent benzene rings are 2.7 (8) and 27.7 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.010 Å
• Disorder in main residue
• R factor = 0.067
• wR factor = 0.156
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         37 Perc.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.756     1.000
            Tmin(prime) and Tmax expected:      0.929     0.965
            RR(prime) =      0.786
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.78
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.57
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
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         S4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
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        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C30
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C22    -   C23    ...       1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C22    -   C27    ...       1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C26    -   C27    ...       1.38 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  20 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
  15 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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

Crystal data

C27H14F10S2	Z = 4
Mr = 592.50	F(000) = 1192
Triclinic, P1	Dx = 1.558 Mg m^−3
Hall symbol: -P 1	Melting point: 374 K
a = 11.873 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.106 (5) Å	Cell parameters from 1802 reflections
c = 16.653 (7) Å	θ = 2.2–20.3°
α = 101.505 (8)°	µ = 0.30 mm^−1
β = 94.504 (9)°	T = 294 K
γ = 92.914 (8)°	Prism, colorless
V = 2525.6 (18) Å^3	0.24 × 0.22 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer	8867 independent reflections
Radiation source: fine-focus sealed tube	3277 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
Tmin = 0.757, Tmax = 1.000	k = −15→15
12920 measured reflections	l = −19→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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0152P)^2 + 5P] where P = (Fo^2 + 2Fc^2)/3
8867 reflections	(Δ/σ)max < 0.001
713 parameters	Δρmax = 0.75 e Å^−3
22 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. ¹H NMR (400 MHz, CDCl₃): δ 2.00 (s, 6H, –CH₃), 6.89–6.94 (m, 4H, J = 8.0 Hz, benzene-H), 7.34 (s, 2H, thiopene-H), 7.48–7.54 (dd, 2H, J = 8.4 Hz, benzene-H), 7.31–7.35 (t, 2H, J = 8.0 Hz, benzene-H); ¹⁹F NMR (376 MHz, CDCl₃): δ 109.48 (2 F), 110.07 (6 F), 131.84 (2 F)

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	0.61525 (16)	0.59832 (15)	0.41980 (12)	0.0732 (6)
S2	0.83728 (15)	0.58654 (13)	0.11507 (12)	0.0615 (5)
S3	0.09021 (15)	0.90376 (14)	0.04565 (11)	0.0608 (5)
S4	0.41358 (17)	0.80106 (15)	0.30283 (14)	0.0801 (7)
F1	0.4578 (5)	0.7235 (4)	0.4973 (3)	0.144 (2)
F2	0.0679 (4)	0.6657 (4)	0.4900 (4)	0.159 (3)
F3	0.4820 (3)	0.2245 (3)	0.2191 (3)	0.0921 (15)
F4	0.5911 (4)	0.2145 (3)	0.3259 (3)	0.0990 (15)
F5	0.7266 (4)	0.1103 (4)	0.2438 (4)	0.133 (2)
F6	0.5954 (4)	0.0814 (4)	0.1460 (3)	0.132 (2)
F7	0.6936 (4)	0.2069 (3)	0.0704 (3)	0.0848 (13)
F8	0.8396 (3)	0.1944 (3)	0.1511 (3)	0.0855 (14)
F9	1.1472 (4)	0.4339 (4)	0.2066 (4)	0.0764 (18)	0.70
F9'	1.0053 (12)	0.6516 (14)	0.0323 (11)	0.140 (7)	0.30
F10	1.3922 (3)	0.6385 (4)	0.0874 (3)	0.1103 (17)
F11	−0.0711 (5)	0.7900 (4)	−0.0691 (3)	0.137 (2)
F12	−0.4503 (4)	0.7067 (4)	−0.0543 (4)	0.147 (2)
F13	0.1006 (4)	1.2374 (3)	0.2657 (3)	0.0927 (14)
F14	−0.0264 (3)	1.1441 (3)	0.3124 (3)	0.0900 (14)
F15	0.0870 (3)	1.1599 (3)	0.4520 (3)	0.0885 (14)
F16	0.1510 (3)	1.3049 (3)	0.4224 (3)	0.0915 (14)
F17	0.3028 (3)	1.1369 (3)	0.4663 (3)	0.0855 (13)
F18	0.3360 (3)	1.2244 (3)	0.3719 (2)	0.0775 (12)
F19	0.6386 (12)	1.0697 (11)	0.4521 (10)	0.123 (7)	0.30
F19'	0.6389 (6)	0.7539 (5)	0.2604 (5)	0.119 (3)	0.70
F20	0.9761 (4)	0.9211 (5)	0.3953 (4)	0.150 (2)
C1	0.3644 (7)	0.6586 (6)	0.4692 (5)	0.074 (2)
C2	0.2622 (8)	0.6934 (7)	0.4955 (6)	0.100 (3)
H2	0.2586	0.7553	0.5336	0.120*
C3	0.1690 (8)	0.6322 (8)	0.4625 (6)	0.098 (3)
C4	0.1686 (8)	0.5444 (7)	0.4073 (6)	0.105 (3)
H4	0.1011	0.5058	0.3862	0.126*
C5	0.2746 (6)	0.5100 (6)	0.3808 (5)	0.080 (2)
H5	0.2760	0.4476	0.3428	0.097*
C6	0.3776 (6)	0.5694 (5)	0.4116 (4)	0.0568 (19)
C7	0.4853 (5)	0.5335 (5)	0.3831 (4)	0.0511 (18)
C8	0.4999 (5)	0.4469 (5)	0.3251 (4)	0.0531 (18)
H8	0.4399	0.4014	0.2982	0.064*
C9	0.6147 (6)	0.4318 (5)	0.3092 (4)	0.0499 (17)
C10	0.6872 (6)	0.5088 (5)	0.3571 (4)	0.0594 (19)
C11	0.8151 (6)	0.5202 (6)	0.3631 (4)	0.089 (3)
H11A	0.8442	0.4524	0.3502	0.133*
H11B	0.8434	0.5543	0.4180	0.133*
H11C	0.8389	0.5612	0.3250	0.133*
C12	0.6481 (5)	0.3405 (5)	0.2506 (4)	0.0462 (17)
C13	0.5924 (6)	0.2350 (5)	0.2501 (5)	0.0582 (19)
C14	0.6587 (7)	0.1567 (6)	0.1946 (5)	0.068 (2)
C15	0.7321 (6)	0.2236 (5)	0.1516 (5)	0.0539 (18)
C16	0.7225 (5)	0.3350 (5)	0.1932 (4)	0.0456 (17)
C17	0.7863 (5)	0.4202 (5)	0.1669 (4)	0.0452 (17)
C18	0.7368 (5)	0.5026 (5)	0.1418 (4)	0.0519 (18)
C19	0.6137 (5)	0.5240 (5)	0.1338 (5)	0.076 (2)
H19A	0.5682	0.4595	0.1252	0.115*
H19B	0.5988	0.5570	0.0878	0.115*
H19C	0.5956	0.5693	0.1832	0.115*
C20	0.9067 (5)	0.4249 (5)	0.1624 (4)	0.0486 (17)
H20	0.9525	0.3743	0.1762	0.058*
C21	0.9477 (5)	0.5110 (5)	0.1360 (4)	0.0493 (17)
C22	1.0638 (5)	0.5445 (5)	0.1234 (4)	0.0462 (17)
C23	1.1572 (6)	0.5046 (5)	0.1588 (4)	0.063 (2)
H23A	1.1442	0.4531	0.1914	0.075*	0.30
C24	1.2706 (7)	0.5362 (6)	0.1495 (5)	0.080 (2)
H24	1.3319	0.5110	0.1759	0.096*
C25	1.2847 (6)	0.6058 (6)	0.0995 (5)	0.070 (2)
C26	1.1982 (6)	0.6474 (5)	0.0615 (4)	0.065 (2)
H26	1.2114	0.6953	0.0284	0.078*
C27	1.0899 (6)	0.6153 (5)	0.0744 (4)	0.0539 (19)
H27A	1.0279	0.6438	0.0477	0.065*	0.70
C28	−0.1604 (7)	0.8012 (7)	−0.0234 (6)	0.076 (2)
C29	−0.2620 (9)	0.7494 (6)	−0.0636 (6)	0.089 (3)
H29	−0.2681	0.7124	−0.1178	0.107*
C30	−0.3502 (8)	0.7581 (7)	−0.0164 (8)	0.092 (3)
C31	−0.3430 (8)	0.8137 (7)	0.0613 (6)	0.098 (3)
H31	−0.4075	0.8181	0.0897	0.117*
C32	−0.2407 (6)	0.8654 (6)	0.1006 (6)	0.078 (3)
H32	−0.2368	0.9034	0.1544	0.093*
C33	−0.1432 (6)	0.8577 (5)	0.0555 (5)	0.0565 (19)
C34	−0.0334 (5)	0.9080 (5)	0.0946 (4)	0.0496 (17)
C35	−0.0127 (5)	0.9629 (5)	0.1727 (4)	0.0516 (18)
H35	−0.0687	0.9750	0.2088	0.062*
C36	0.1050 (6)	1.0012 (5)	0.1951 (4)	0.0501 (17)
C37	0.1690 (6)	0.9730 (5)	0.1311 (4)	0.0565 (19)
C38	0.2946 (5)	0.9975 (5)	0.1268 (4)	0.072 (2)
H38A	0.3188	1.0619	0.1642	0.108*
H38B	0.3078	1.0038	0.0718	0.108*
H38C	0.3365	0.9422	0.1415	0.108*
C39	0.1463 (5)	1.0649 (5)	0.2755 (4)	0.0491 (17)
C40	0.0872 (6)	1.1624 (6)	0.3105 (5)	0.0596 (19)
C41	0.1444 (6)	1.2006 (6)	0.3972 (5)	0.063 (2)
C42	0.2605 (6)	1.1536 (5)	0.3929 (4)	0.0562 (19)
C43	0.2393 (5)	1.0569 (5)	0.3259 (4)	0.0499 (17)
C44	0.3199 (6)	0.9744 (5)	0.3207 (4)	0.0518 (18)
C45	0.2939 (6)	0.8685 (5)	0.3005 (4)	0.060 (2)
C46	0.1797 (6)	0.8102 (5)	0.2821 (5)	0.081 (2)
H46A	0.1238	0.8533	0.3071	0.121*
H46B	0.1812	0.7476	0.3038	0.121*
H46C	0.1611	0.7923	0.2236	0.121*
C47	0.4394 (6)	0.9983 (5)	0.3394 (4)	0.059 (2)
H47	0.4713	1.0664	0.3555	0.071*
C48	0.5026 (6)	0.9137 (5)	0.3318 (4)	0.063 (2)
C49	0.6298 (3)	0.9142 (5)	0.3493 (3)	0.064 (2)
C50	0.6873 (5)	0.9977 (4)	0.4045 (3)	0.084 (3)
H50A	0.6463	1.0539	0.4317	0.101*	0.70
C51	0.8042 (5)	1.0000 (5)	0.4203 (3)	0.104 (3)
H51	0.8427	1.0559	0.4572	0.125*
C52	0.8637 (3)	0.9188 (6)	0.3809 (4)	0.112 (4)
C53	0.8062 (6)	0.8353 (5)	0.3258 (4)	0.104 (3)
H53	0.8460	0.7809	0.2994	0.125*
C54	0.6893 (6)	0.8330 (4)	0.3100 (3)	0.087 (3)
H54A	0.6496	0.7753	0.2719	0.105*	0.30

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0689 (14)	0.0722 (14)	0.0683 (14)	−0.0090 (11)	0.0111 (11)	−0.0080 (11)
S2	0.0500 (11)	0.0514 (11)	0.0896 (15)	0.0053 (9)	0.0097 (11)	0.0282 (11)
S3	0.0609 (12)	0.0640 (12)	0.0585 (13)	0.0127 (10)	0.0091 (10)	0.0117 (10)
S4	0.0737 (14)	0.0542 (13)	0.1167 (19)	0.0099 (11)	0.0055 (13)	0.0277 (13)
F1	0.119 (5)	0.138 (5)	0.149 (5)	0.012 (4)	0.022 (4)	−0.037 (4)
F2	0.084 (4)	0.155 (5)	0.218 (7)	0.039 (3)	0.054 (4)	−0.030 (5)
F3	0.050 (3)	0.077 (3)	0.136 (4)	−0.015 (2)	0.014 (3)	−0.007 (3)
F4	0.149 (4)	0.079 (3)	0.071 (3)	−0.030 (3)	0.032 (3)	0.021 (3)
F5	0.127 (4)	0.142 (5)	0.178 (6)	0.063 (4)	0.066 (4)	0.110 (4)
F6	0.134 (4)	0.083 (4)	0.156 (5)	−0.056 (3)	0.081 (4)	−0.043 (3)
F7	0.116 (4)	0.071 (3)	0.065 (3)	−0.004 (2)	0.013 (3)	0.009 (2)
F8	0.060 (3)	0.065 (3)	0.136 (4)	0.013 (2)	0.029 (3)	0.021 (3)
F9	0.051 (3)	0.095 (4)	0.104 (5)	−0.002 (3)	0.002 (3)	0.075 (4)
F9'	0.115 (15)	0.153 (17)	0.160 (19)	−0.023 (13)	0.033 (14)	0.053 (14)
F10	0.050 (3)	0.134 (4)	0.167 (5)	0.005 (3)	0.035 (3)	0.068 (4)
F11	0.126 (5)	0.166 (5)	0.095 (4)	0.000 (4)	−0.006 (4)	−0.020 (4)
F12	0.101 (4)	0.143 (5)	0.181 (6)	−0.046 (4)	−0.049 (4)	0.036 (4)
F13	0.132 (4)	0.069 (3)	0.086 (3)	0.033 (3)	0.013 (3)	0.029 (3)
F14	0.054 (3)	0.104 (3)	0.099 (4)	0.016 (2)	0.001 (2)	−0.010 (3)
F15	0.076 (3)	0.119 (4)	0.072 (3)	−0.002 (3)	0.023 (3)	0.018 (3)
F16	0.084 (3)	0.064 (3)	0.113 (4)	0.009 (2)	0.002 (3)	−0.013 (3)
F17	0.087 (3)	0.106 (4)	0.060 (3)	0.007 (3)	−0.006 (3)	0.013 (3)
F18	0.067 (3)	0.062 (3)	0.099 (3)	−0.014 (2)	0.019 (2)	0.005 (2)
F19	0.075 (11)	0.095 (13)	0.179 (19)	0.013 (9)	−0.022 (11)	−0.009 (12)
F19'	0.097 (5)	0.110 (6)	0.134 (7)	0.019 (4)	0.005 (5)	−0.013 (5)
F20	0.054 (3)	0.236 (7)	0.186 (6)	0.022 (4)	0.023 (3)	0.097 (5)
C1	0.056 (6)	0.076 (6)	0.079 (6)	−0.021 (5)	0.010 (5)	−0.006 (5)
C2	0.086 (7)	0.086 (7)	0.119 (8)	0.016 (6)	0.036 (7)	−0.011 (6)
C3	0.062 (6)	0.103 (8)	0.127 (9)	0.020 (6)	0.034 (6)	0.010 (7)
C4	0.104 (8)	0.075 (7)	0.121 (8)	0.012 (6)	0.020 (6)	−0.020 (6)
C5	0.046 (5)	0.078 (6)	0.117 (7)	0.012 (5)	0.022 (5)	0.011 (5)
C6	0.070 (6)	0.051 (5)	0.052 (5)	0.011 (4)	0.018 (4)	0.012 (4)
C7	0.051 (4)	0.058 (5)	0.043 (4)	−0.002 (4)	0.009 (4)	0.005 (4)
C8	0.049 (5)	0.058 (5)	0.050 (5)	−0.007 (4)	0.012 (4)	0.005 (4)
C9	0.054 (5)	0.049 (4)	0.044 (4)	−0.007 (4)	0.010 (4)	0.005 (4)
C10	0.055 (5)	0.068 (5)	0.054 (5)	0.001 (4)	0.018 (4)	0.006 (4)
C11	0.056 (5)	0.117 (7)	0.076 (6)	−0.013 (5)	0.006 (4)	−0.017 (5)
C12	0.044 (4)	0.047 (4)	0.047 (4)	−0.003 (3)	0.008 (4)	0.011 (4)
C13	0.058 (5)	0.063 (5)	0.053 (5)	−0.005 (4)	0.012 (4)	0.011 (4)
C14	0.072 (6)	0.053 (5)	0.088 (6)	0.008 (4)	0.021 (5)	0.029 (5)
C15	0.046 (5)	0.060 (5)	0.061 (5)	0.009 (4)	0.016 (4)	0.020 (4)
C16	0.040 (4)	0.040 (4)	0.058 (5)	0.003 (3)	0.014 (4)	0.011 (4)
C17	0.041 (4)	0.045 (4)	0.053 (5)	−0.001 (3)	0.015 (3)	0.015 (3)
C18	0.044 (4)	0.049 (4)	0.064 (5)	0.003 (3)	0.008 (4)	0.015 (4)
C19	0.049 (5)	0.073 (5)	0.112 (7)	0.009 (4)	0.009 (5)	0.027 (5)
C20	0.045 (4)	0.051 (4)	0.056 (5)	0.007 (3)	0.012 (4)	0.022 (4)
C21	0.050 (4)	0.046 (4)	0.054 (5)	0.008 (3)	0.011 (4)	0.013 (4)
C22	0.039 (4)	0.046 (4)	0.056 (5)	−0.002 (3)	0.012 (4)	0.015 (4)
C23	0.051 (5)	0.066 (5)	0.074 (6)	0.002 (4)	0.003 (4)	0.024 (4)
C24	0.068 (6)	0.081 (6)	0.104 (7)	0.006 (5)	0.016 (5)	0.045 (5)
C25	0.032 (4)	0.078 (6)	0.105 (7)	0.002 (4)	0.022 (4)	0.020 (5)
C26	0.053 (5)	0.065 (5)	0.087 (6)	0.000 (4)	0.028 (5)	0.031 (4)
C27	0.044 (5)	0.059 (5)	0.064 (5)	0.005 (4)	0.007 (4)	0.024 (4)
C28	0.063 (6)	0.084 (6)	0.084 (7)	0.021 (5)	0.015 (6)	0.014 (6)
C29	0.088 (7)	0.074 (6)	0.088 (7)	−0.006 (5)	−0.023 (6)	−0.008 (5)
C30	0.064 (7)	0.082 (7)	0.129 (10)	−0.015 (6)	−0.018 (7)	0.034 (7)
C31	0.104 (9)	0.102 (8)	0.091 (8)	0.014 (6)	0.014 (7)	0.027 (6)
C32	0.025 (4)	0.075 (6)	0.131 (8)	−0.008 (4)	−0.010 (5)	0.025 (5)
C33	0.070 (6)	0.040 (4)	0.055 (5)	0.003 (4)	−0.011 (4)	0.004 (4)
C34	0.049 (4)	0.046 (4)	0.053 (5)	0.011 (3)	0.000 (4)	0.009 (4)
C35	0.048 (5)	0.056 (5)	0.052 (5)	0.005 (4)	0.010 (4)	0.012 (4)
C36	0.055 (5)	0.044 (4)	0.050 (5)	0.005 (4)	0.007 (4)	0.007 (4)
C37	0.058 (5)	0.058 (5)	0.055 (5)	0.006 (4)	0.008 (4)	0.016 (4)
C38	0.050 (5)	0.089 (6)	0.079 (6)	0.001 (4)	0.012 (4)	0.022 (5)
C39	0.042 (4)	0.050 (4)	0.055 (5)	0.005 (3)	0.007 (4)	0.012 (4)
C40	0.049 (5)	0.070 (5)	0.060 (5)	0.007 (4)	0.003 (4)	0.013 (4)
C41	0.057 (5)	0.062 (5)	0.072 (6)	0.001 (4)	0.014 (5)	0.013 (5)
C42	0.053 (5)	0.065 (5)	0.051 (5)	−0.008 (4)	0.001 (4)	0.016 (4)
C43	0.047 (4)	0.045 (4)	0.058 (5)	−0.006 (3)	0.005 (4)	0.014 (4)
C44	0.050 (5)	0.047 (4)	0.061 (5)	−0.002 (4)	0.007 (4)	0.018 (4)
C45	0.058 (5)	0.052 (5)	0.073 (5)	−0.003 (4)	0.000 (4)	0.021 (4)
C46	0.075 (6)	0.055 (5)	0.110 (7)	−0.008 (4)	−0.001 (5)	0.020 (5)
C47	0.065 (5)	0.047 (5)	0.071 (5)	0.000 (4)	0.005 (4)	0.027 (4)
C48	0.063 (5)	0.062 (5)	0.071 (5)	−0.001 (4)	0.004 (4)	0.031 (4)
C49	0.065 (5)	0.067 (5)	0.073 (5)	0.016 (4)	0.012 (4)	0.037 (4)
C50	0.063 (5)	0.094 (6)	0.099 (6)	−0.008 (5)	−0.012 (5)	0.043 (5)
C51	0.061 (6)	0.130 (8)	0.141 (9)	0.005 (6)	0.012 (6)	0.075 (7)
C52	0.047 (6)	0.191 (12)	0.128 (10)	0.018 (7)	0.017 (6)	0.098 (9)
C53	0.062 (7)	0.153 (10)	0.114 (9)	0.019 (6)	0.018 (6)	0.060 (7)
C54	0.085 (6)	0.094 (6)	0.089 (6)	0.010 (5)	0.009 (5)	0.031 (5)

Geometric parameters (Å, º)

S1—C10	1.717 (7)	C19—H19B	0.9600
S1—C7	1.729 (6)	C19—H19C	0.9600
S2—C18	1.725 (6)	C20—C21	1.372 (7)
S2—C21	1.737 (6)	C20—H20	0.9300
S3—C37	1.707 (7)	C21—C22	1.469 (8)
S3—C34	1.732 (6)	C22—C23	1.389 (8)
S4—C45	1.713 (7)	C22—C27	1.391 (8)
S4—C48	1.734 (7)	C23—C24	1.419 (9)
F1—C1	1.355 (8)	C23—H23A	0.9600
F2—C3	1.378 (9)	C24—C25	1.365 (9)
F3—C13	1.360 (7)	C24—H24	0.9300
F4—C13	1.343 (7)	C25—C26	1.358 (9)
F5—C14	1.355 (8)	C26—C27	1.378 (8)
F6—C14	1.305 (8)	C26—H26	0.9300
F7—C15	1.365 (7)	C27—H27A	0.9600
F8—C15	1.351 (7)	C28—C33	1.369 (9)
F9—C23	1.343 (6)	C28—C29	1.405 (10)
F9'—C27	1.340 (9)	C29—C30	1.355 (11)
F10—C25	1.369 (7)	C29—H29	0.9300
F11—C28	1.349 (8)	C30—C31	1.346 (11)
F12—C30	1.377 (9)	C31—C32	1.406 (10)
F13—C40	1.359 (7)	C31—H31	0.9300
F14—C40	1.362 (7)	C32—C33	1.425 (9)
F15—C41	1.354 (7)	C32—H32	0.9300
F16—C41	1.344 (7)	C33—C34	1.472 (9)
F17—C42	1.347 (7)	C34—C35	1.352 (8)
F18—C42	1.371 (7)	C35—C36	1.454 (8)
F19—C50	1.297 (9)	C35—H35	0.9300
F19'—C54	1.277 (6)	C36—C37	1.359 (8)
F20—C52	1.335 (6)	C36—C39	1.462 (8)
C1—C6	1.381 (9)	C37—C38	1.520 (8)
C1—C2	1.390 (10)	C38—H38A	0.9600
C2—C3	1.345 (11)	C38—H38B	0.9600
C2—H2	0.9300	C38—H38C	0.9600
C3—C4	1.322 (10)	C39—C43	1.355 (8)
C4—C5	1.431 (10)	C39—C40	1.524 (8)
C4—H4	0.9300	C40—C41	1.523 (9)
C5—C6	1.418 (9)	C41—C42	1.540 (9)
C5—H5	0.9300	C42—C43	1.508 (8)
C6—C7	1.466 (8)	C43—C44	1.474 (8)
C7—C8	1.363 (8)	C44—C45	1.374 (8)
C8—C9	1.425 (8)	C44—C47	1.434 (8)
C8—H8	0.9300	C45—C46	1.501 (8)
C9—C10	1.370 (8)	C46—H46A	0.9600
C9—C12	1.478 (8)	C46—H46B	0.9600
C10—C11	1.512 (8)	C46—H46C	0.9600
C11—H11A	0.9600	C47—C48	1.360 (8)
C11—H11B	0.9600	C47—H47	0.9300
C11—H11C	0.9600	C48—C49	1.516 (8)
C12—C16	1.345 (8)	C49—C50	1.3900
C12—C13	1.500 (8)	C49—C54	1.3900
C13—C14	1.532 (9)	C50—C51	1.3900
C14—C15	1.520 (9)	C50—H50A	0.9600
C15—C16	1.501 (8)	C51—C52	1.3900
C16—C17	1.474 (8)	C51—H51	0.9300
C17—C18	1.376 (8)	C52—C53	1.3900
C17—C20	1.436 (8)	C53—C54	1.3900
C18—C19	1.503 (8)	C53—H53	0.9300
C19—H19A	0.9600	C54—H54A	0.9600
C10—S1—C7	92.8 (3)	C26—C27—H27A	117.8
C18—S2—C21	93.0 (3)	C22—C27—H27A	117.5
C37—S3—C34	93.0 (3)	F11—C28—C33	118.4 (8)
C45—S4—C48	93.3 (3)	F11—C28—C29	114.3 (9)
F1—C1—C6	117.3 (8)	C33—C28—C29	127.3 (8)
F1—C1—C2	116.3 (8)	C30—C29—C28	113.9 (9)
C6—C1—C2	126.0 (7)	C30—C29—H29	123.0
C3—C2—C1	115.9 (8)	C28—C29—H29	123.0
C3—C2—H2	122.0	C31—C30—C29	123.5 (9)
C1—C2—H2	122.0	C31—C30—F12	121.6 (11)
C4—C3—C2	124.8 (9)	C29—C30—F12	114.8 (10)
C4—C3—F2	119.3 (10)	C30—C31—C32	121.8 (9)
C2—C3—F2	115.9 (9)	C30—C31—H31	119.1
C3—C4—C5	118.4 (9)	C32—C31—H31	119.1
C3—C4—H4	120.8	C31—C32—C33	117.9 (8)
C5—C4—H4	120.8	C31—C32—H32	121.0
C6—C5—C4	121.0 (8)	C33—C32—H32	121.0
C6—C5—H5	119.5	C28—C33—C32	115.5 (7)
C4—C5—H5	119.5	C28—C33—C34	124.5 (8)
C1—C6—C5	113.8 (7)	C32—C33—C34	120.1 (7)
C1—C6—C7	126.0 (7)	C35—C34—C33	126.2 (6)
C5—C6—C7	120.3 (7)	C35—C34—S3	109.8 (5)
C8—C7—C6	126.8 (6)	C33—C34—S3	123.9 (6)
C8—C7—S1	109.7 (5)	C34—C35—C36	114.0 (6)
C6—C7—S1	123.5 (5)	C34—C35—H35	123.0
C7—C8—C9	114.5 (6)	C36—C35—H35	123.0
C7—C8—H8	122.7	C37—C36—C35	111.2 (6)
C9—C8—H8	122.7	C37—C36—C39	125.2 (6)
C10—C9—C8	111.5 (6)	C35—C36—C39	123.5 (6)
C10—C9—C12	125.8 (6)	C36—C37—C38	129.0 (6)
C8—C9—C12	122.6 (6)	C36—C37—S3	112.0 (5)
C9—C10—C11	129.1 (6)	C38—C37—S3	119.0 (5)
C9—C10—S1	111.5 (5)	C37—C38—H38A	109.5
C11—C10—S1	119.4 (5)	C37—C38—H38B	109.5
C10—C11—H11A	109.5	H38A—C38—H38B	109.5
C10—C11—H11B	109.5	C37—C38—H38C	109.5
H11A—C11—H11B	109.5	H38A—C38—H38C	109.5
C10—C11—H11C	109.5	H38B—C38—H38C	109.5
H11A—C11—H11C	109.5	C43—C39—C36	130.0 (6)
H11B—C11—H11C	109.5	C43—C39—C40	109.8 (6)
C16—C12—C9	130.0 (6)	C36—C39—C40	120.0 (6)
C16—C12—C13	111.2 (6)	F13—C40—F14	106.5 (6)
C9—C12—C13	118.7 (6)	F13—C40—C41	109.8 (6)
F4—C13—F3	105.1 (6)	F14—C40—C41	110.6 (6)
F4—C13—C12	112.6 (6)	F13—C40—C39	111.5 (6)
F3—C13—C12	113.0 (6)	F14—C40—C39	113.3 (6)
F4—C13—C14	111.8 (6)	C41—C40—C39	105.1 (6)
F3—C13—C14	108.7 (6)	F16—C41—F15	107.2 (6)
C12—C13—C14	105.7 (6)	F16—C41—C40	113.9 (6)
F6—C14—F5	106.0 (6)	F15—C41—C40	110.2 (6)
F6—C14—C15	115.4 (7)	F16—C41—C42	113.7 (6)
F5—C14—C15	108.8 (6)	F15—C41—C42	108.4 (6)
F6—C14—C13	114.1 (7)	C40—C41—C42	103.3 (6)
F5—C14—C13	107.7 (7)	F17—C42—F18	106.0 (5)
C15—C14—C13	104.5 (6)	F17—C42—C43	115.0 (6)
F8—C15—F7	104.2 (5)	F18—C42—C43	111.3 (6)
F8—C15—C16	113.9 (6)	F17—C42—C41	112.3 (6)
F7—C15—C16	111.0 (5)	F18—C42—C41	108.3 (6)
F8—C15—C14	111.9 (6)	C43—C42—C41	103.9 (6)
F7—C15—C14	109.1 (6)	C39—C43—C44	130.1 (6)
C16—C15—C14	106.8 (6)	C39—C43—C42	110.4 (6)
C12—C16—C17	129.2 (6)	C44—C43—C42	119.4 (6)
C12—C16—C15	110.4 (5)	C45—C44—C47	111.4 (6)
C17—C16—C15	120.4 (5)	C45—C44—C43	126.8 (6)
C18—C17—C20	112.4 (5)	C47—C44—C43	121.8 (6)
C18—C17—C16	123.8 (6)	C44—C45—C46	128.9 (6)
C20—C17—C16	123.8 (6)	C44—C45—S4	111.2 (5)
C17—C18—C19	129.1 (6)	C46—C45—S4	119.8 (5)
C17—C18—S2	110.9 (5)	C45—C46—H46A	109.5
C19—C18—S2	120.0 (5)	C45—C46—H46B	109.5
C18—C19—H19A	109.5	H46A—C46—H46B	109.5
C18—C19—H19B	109.5	C45—C46—H46C	109.5
H19A—C19—H19B	109.5	H46A—C46—H46C	109.5
C18—C19—H19C	109.5	H46B—C46—H46C	109.5
H19A—C19—H19C	109.5	C48—C47—C44	114.8 (6)
H19B—C19—H19C	109.5	C48—C47—H47	122.6
C21—C20—C17	113.6 (6)	C44—C47—H47	122.6
C21—C20—H20	123.2	C47—C48—C49	126.8 (6)
C17—C20—H20	123.2	C47—C48—S4	109.2 (5)
C20—C21—C22	130.6 (6)	C49—C48—S4	123.9 (5)
C20—C21—S2	110.1 (5)	C50—C49—C54	120.0
C22—C21—S2	119.4 (5)	C50—C49—C48	119.4 (5)
C23—C22—C27	114.6 (6)	C54—C49—C48	120.6 (5)
C23—C22—C21	121.5 (6)	F19—C50—C49	124.4 (9)
C27—C22—C21	123.8 (6)	F19—C50—C51	115.0 (9)
F9—C23—C22	122.4 (6)	C49—C50—C51	120.0
F9—C23—C24	114.2 (6)	C49—C50—H50A	120.0
C22—C23—C24	123.3 (6)	C51—C50—H50A	120.0
C22—C23—H23A	118.3	C50—C51—C52	120.0
C24—C23—H23A	118.4	C50—C51—H51	120.0
C25—C24—C23	116.2 (7)	C52—C51—H51	120.0
C25—C24—H24	121.9	F20—C52—C53	119.7 (6)
C23—C24—H24	121.9	F20—C52—C51	120.2 (6)
C26—C25—C24	124.2 (7)	C53—C52—C51	120.0
C26—C25—F10	116.9 (7)	C52—C53—C54	120.0
C24—C25—F10	118.9 (7)	C52—C53—H53	120.0
C25—C26—C27	116.9 (7)	C54—C53—H53	120.0
C25—C26—H26	121.6	F19'—C54—C53	118.3 (6)
C27—C26—H26	121.6	F19'—C54—C49	121.6 (6)
F9'—C27—C26	116.2 (10)	C53—C54—C49	120.0
F9'—C27—C22	118.9 (10)	C53—C54—H54A	120.0
C26—C27—C22	124.7 (7)	C49—C54—H54A	120.0
F1—C1—C2—C3	175.1 (8)	F11—C28—C29—C30	177.9 (7)
C6—C1—C2—C3	1.7 (14)	C33—C28—C29—C30	−0.3 (13)
C1—C2—C3—C4	−1.0 (16)	C28—C29—C30—C31	1.8 (14)
C1—C2—C3—F2	178.6 (7)	C28—C29—C30—F12	−179.2 (7)
C2—C3—C4—C5	0.8 (16)	C29—C30—C31—C32	−1.8 (15)
F2—C3—C4—C5	−178.8 (8)	F12—C30—C31—C32	179.2 (7)
C3—C4—C5—C6	−1.2 (13)	C30—C31—C32—C33	0.2 (12)
F1—C1—C6—C5	−175.5 (7)	F11—C28—C33—C32	−179.2 (7)
C2—C1—C6—C5	−2.1 (12)	C29—C28—C33—C32	−1.2 (12)
F1—C1—C6—C7	5.8 (12)	F11—C28—C33—C34	0.3 (11)
C2—C1—C6—C7	179.1 (8)	C29—C28—C33—C34	178.4 (7)
C4—C5—C6—C1	1.8 (11)	C31—C32—C33—C28	1.2 (10)
C4—C5—C6—C7	−179.4 (7)	C31—C32—C33—C34	−178.4 (6)
C1—C6—C7—C8	−178.6 (7)	C28—C33—C34—C35	−178.9 (7)
C5—C6—C7—C8	2.7 (11)	C32—C33—C34—C35	0.7 (10)
C1—C6—C7—S1	1.0 (10)	C28—C33—C34—S3	0.5 (10)
C5—C6—C7—S1	−177.6 (6)	C32—C33—C34—S3	−179.9 (5)
C10—S1—C7—C8	0.0 (5)	C37—S3—C34—C35	1.3 (5)
C10—S1—C7—C6	−179.7 (6)	C37—S3—C34—C33	−178.2 (5)
C6—C7—C8—C9	179.4 (6)	C33—C34—C35—C36	178.4 (6)
S1—C7—C8—C9	−0.3 (7)	S3—C34—C35—C36	−1.1 (7)
C7—C8—C9—C10	0.4 (8)	C34—C35—C36—C37	0.2 (8)
C7—C8—C9—C12	177.8 (6)	C34—C35—C36—C39	178.1 (6)
C8—C9—C10—C11	176.7 (7)	C35—C36—C37—C38	178.9 (6)
C12—C9—C10—C11	−0.6 (12)	C39—C36—C37—C38	1.1 (11)
C8—C9—C10—S1	−0.4 (7)	C35—C36—C37—S3	0.8 (7)
C12—C9—C10—S1	−177.6 (5)	C39—C36—C37—S3	−177.1 (5)
C7—S1—C10—C9	0.2 (6)	C34—S3—C37—C36	−1.2 (5)
C7—S1—C10—C11	−177.2 (6)	C34—S3—C37—C38	−179.6 (5)
C10—C9—C12—C16	−46.3 (11)	C37—C36—C39—C43	−47.9 (11)
C8—C9—C12—C16	136.7 (7)	C35—C36—C39—C43	134.5 (7)
C10—C9—C12—C13	135.1 (7)	C37—C36—C39—C40	126.5 (7)
C8—C9—C12—C13	−41.9 (9)	C35—C36—C39—C40	−51.2 (9)
C16—C12—C13—F4	132.9 (6)	C43—C39—C40—F13	108.3 (7)
C9—C12—C13—F4	−48.2 (8)	C36—C39—C40—F13	−67.1 (8)
C16—C12—C13—F3	−108.2 (7)	C43—C39—C40—F14	−131.5 (6)
C9—C12—C13—F3	70.7 (8)	C36—C39—C40—F14	53.0 (8)
C16—C12—C13—C14	10.6 (8)	C43—C39—C40—C41	−10.6 (7)
C9—C12—C13—C14	−170.6 (6)	C36—C39—C40—C41	173.9 (6)
F4—C13—C14—F6	98.1 (8)	F13—C40—C41—F16	27.0 (8)
F3—C13—C14—F6	−17.5 (9)	F14—C40—C41—F16	−90.3 (7)
C12—C13—C14—F6	−139.0 (6)	C39—C40—C41—F16	147.0 (6)
F4—C13—C14—F5	−19.3 (9)	F13—C40—C41—F15	147.5 (6)
F3—C13—C14—F5	−134.9 (6)	F14—C40—C41—F15	30.2 (8)
C12—C13—C14—F5	103.6 (7)	C39—C40—C41—F15	−92.4 (7)
F4—C13—C14—C15	−134.9 (6)	F13—C40—C41—C42	−96.9 (6)
F3—C13—C14—C15	109.5 (7)	F14—C40—C41—C42	145.9 (6)
C12—C13—C14—C15	−12.1 (8)	C39—C40—C41—C42	23.2 (7)
F6—C14—C15—F8	−98.8 (8)	F16—C41—C42—F17	84.1 (8)
F5—C14—C15—F8	20.2 (9)	F15—C41—C42—F17	−35.0 (8)
C13—C14—C15—F8	135.0 (6)	C40—C41—C42—F17	−151.9 (6)
F6—C14—C15—F7	15.9 (9)	F16—C41—C42—F18	−32.6 (9)
F5—C14—C15—F7	134.9 (6)	F15—C41—C42—F18	−151.7 (6)
C13—C14—C15—F7	−110.2 (7)	C40—C41—C42—F18	91.4 (7)
F6—C14—C15—C16	136.0 (7)	F16—C41—C42—C43	−151.0 (6)
F5—C14—C15—C16	−105.0 (7)	F15—C41—C42—C43	89.9 (7)
C13—C14—C15—C16	9.8 (8)	C40—C41—C42—C43	−27.1 (7)
C9—C12—C16—C17	−5.7 (12)	C36—C39—C43—C44	−8.5 (11)
C13—C12—C16—C17	173.0 (6)	C40—C39—C43—C44	176.6 (6)
C9—C12—C16—C15	177.0 (6)	C36—C39—C43—C42	167.5 (6)
C13—C12—C16—C15	−4.4 (8)	C40—C39—C43—C42	−7.3 (7)
F8—C15—C16—C12	−127.7 (6)	F17—C42—C43—C39	145.1 (6)
F7—C15—C16—C12	115.1 (6)	F18—C42—C43—C39	−94.3 (7)
C14—C15—C16—C12	−3.7 (8)	C41—C42—C43—C39	22.0 (7)
F8—C15—C16—C17	54.7 (8)	F17—C42—C43—C44	−38.3 (8)
F7—C15—C16—C17	−62.5 (7)	F18—C42—C43—C44	82.2 (7)
C14—C15—C16—C17	178.7 (6)	C41—C42—C43—C44	−161.4 (6)
C12—C16—C17—C18	−53.3 (10)	C39—C43—C44—C45	−42.4 (11)
C15—C16—C17—C18	123.9 (7)	C42—C43—C44—C45	141.8 (7)
C12—C16—C17—C20	128.6 (7)	C39—C43—C44—C47	139.4 (7)
C15—C16—C17—C20	−54.3 (9)	C42—C43—C44—C47	−36.3 (9)
C20—C17—C18—C19	177.1 (6)	C47—C44—C45—C46	175.8 (7)
C16—C17—C18—C19	−1.2 (11)	C43—C44—C45—C46	−2.6 (12)
C20—C17—C18—S2	−1.3 (7)	C47—C44—C45—S4	−1.0 (8)
C16—C17—C18—S2	−179.7 (5)	C43—C44—C45—S4	−179.4 (5)
C21—S2—C18—C17	0.8 (5)	C48—S4—C45—C44	0.3 (6)
C21—S2—C18—C19	−177.8 (6)	C48—S4—C45—C46	−176.8 (6)
C18—C17—C20—C21	1.4 (8)	C45—C44—C47—C48	1.5 (9)
C16—C17—C20—C21	179.7 (6)	C43—C44—C47—C48	179.9 (6)
C17—C20—C21—C22	179.8 (6)	C44—C47—C48—C49	−178.3 (6)
C17—C20—C21—S2	−0.8 (7)	C44—C47—C48—S4	−1.2 (8)
C18—S2—C21—C20	0.0 (5)	C45—S4—C48—C47	0.5 (6)
C18—S2—C21—C22	179.5 (5)	C45—S4—C48—C49	177.7 (6)
C20—C21—C22—C23	−18.0 (11)	C47—C48—C49—C50	25.2 (9)
S2—C21—C22—C23	162.6 (5)	S4—C48—C49—C50	−151.6 (4)
C20—C21—C22—C27	160.2 (7)	C47—C48—C49—C54	−153.9 (6)
S2—C21—C22—C27	−19.2 (9)	S4—C48—C49—C54	29.4 (7)
C27—C22—C23—F9	−178.7 (7)	C54—C49—C50—F19	−170.5 (12)
C21—C22—C23—F9	−0.3 (11)	C48—C49—C50—F19	10.5 (12)
C27—C22—C23—C24	2.8 (10)	C54—C49—C50—C51	0.0
C21—C22—C23—C24	−178.8 (6)	C48—C49—C50—C51	−179.0 (5)
F9—C23—C24—C25	178.2 (7)	F19—C50—C51—C52	171.3 (11)
C22—C23—C24—C25	−3.2 (11)	C49—C50—C51—C52	0.0
C23—C24—C25—C26	2.1 (12)	C50—C51—C52—F20	179.3 (5)
C23—C24—C25—F10	−179.4 (6)	C50—C51—C52—C53	0.0
C24—C25—C26—C27	−0.8 (12)	F20—C52—C53—C54	−179.4 (5)
F10—C25—C26—C27	−179.3 (6)	C51—C52—C53—C54	0.0
C25—C26—C27—F9'	−175.7 (12)	C52—C53—C54—F19'	−178.4 (6)
C25—C26—C27—C22	0.4 (11)	C52—C53—C54—C49	0.0
C23—C22—C27—F9'	174.7 (12)	C50—C49—C54—F19'	178.4 (7)
C21—C22—C27—F9'	−3.7 (15)	C48—C49—C54—F19'	−2.6 (7)
C23—C22—C27—C26	−1.4 (10)	C50—C49—C54—C53	0.0
C21—C22—C27—C26	−179.7 (6)	C48—C49—C54—C53	179.0 (5)