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

The title compound, C₂₇H₁₄F₁₀S₂, is a symmetrical photochromic diaryl­ethene derivative and crystallizes with two independent mol­ecules in the asymmetric unit. Both adopt a photoactive anti­parallel conformation. The distances between the potentially photochemically active methyl-substituted C atoms on each thio­phene ring in the two mol­ecules are 3.556 (3) and 3.853 (3) Å. The photochromic behavior of the crystals is described.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.052
• wR factor = 0.152
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    F2     -   C4      ..       9.17 su
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C40
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C41

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.829     1.000
            Tmin(prime) and Tmax expected:      0.927     0.952
            RR(prime) =      0.851
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT213_ALERT_2_C Atom F16     has ADP max/min Ratio .............       3.10 prola
PLAT220_ALERT_2_C Large Non-Solvent    F     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C42
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   8 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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.

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

Crystal data

C27H14F10S2	F(000) = 2384
Mr = 592.50	Dx = 1.584 Mg m^−3
Monoclinic, P21/c	Melting point: 407 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 19.126 (4) Å	Cell parameters from 5320 reflections
b = 12.098 (3) Å	θ = 2.7–22.6°
c = 21.528 (5) Å	µ = 0.31 mm^−1
β = 93.876 (4)°	T = 294 K
V = 4969.8 (18) Å^3	Prism, colorless
Z = 8	0.24 × 0.22 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	8768 independent reflections
Radiation source: fine-focus sealed tube	5160 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.829, Tmax = 1.000	k = −12→14
24860 measured reflections	l = −25→23

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 3.5743P] where P = (Fo^2 + 2Fc^2)/3
8768 reflections	(Δ/σ)max < 0.001
707 parameters	Δρmax = 0.78 e Å^−3
12 restraints	Δρmin = −0.49 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. 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
S1	0.17778 (6)	0.44758 (8)	0.18115 (5)	0.0554 (3)
S2	0.06786 (5)	0.72733 (9)	0.35894 (5)	0.0546 (3)
S3	0.39276 (6)	0.28114 (9)	0.68684 (5)	0.0585 (3)
S4	0.14965 (6)	0.11629 (9)	0.52501 (5)	0.0547 (3)
F1	0.13423 (17)	−0.1020 (2)	0.16616 (15)	0.0993 (10)
F2	0.24684 (19)	−0.0582 (2)	0.24158 (16)	0.1031 (10)
F3	0.40133 (12)	0.4698 (2)	0.31832 (12)	0.0713 (7)
F4	0.34744 (13)	0.40922 (17)	0.39700 (12)	0.0661 (7)
F5	0.42849 (12)	0.6598 (2)	0.37060 (13)	0.0728 (7)
F6	0.42683 (12)	0.5576 (2)	0.45331 (11)	0.0688 (7)
F7	0.33422 (14)	0.7655 (2)	0.42666 (15)	0.0920 (10)
F8	0.30254 (14)	0.6215 (3)	0.47636 (12)	0.0832 (9)
F9	0.14720 (17)	1.2366 (2)	0.36677 (14)	0.0881 (9)
F10	0.02291 (18)	1.2679 (2)	0.30518 (15)	0.1030 (10)
F11	0.02378 (18)	−0.3980 (3)	0.54240 (17)	0.1224 (13)
F12	0.16101 (19)	−0.4123 (2)	0.52942 (18)	0.1151 (12)
F13	0.32741 (18)	0.1354 (4)	0.37153 (14)	0.1341 (15)
F14	0.3678 (2)	−0.0147 (2)	0.41077 (17)	0.1283 (15)
F15	0.4473 (3)	0.1959 (4)	0.36207 (16)	0.172 (2)
F16	0.48647 (19)	0.0545 (4)	0.4083 (3)	0.186 (2)
F17	0.47399 (13)	0.3102 (2)	0.45565 (12)	0.0719 (7)
F18	0.51941 (13)	0.1683 (3)	0.50162 (14)	0.0944 (10)
F19	0.4073 (2)	0.8283 (2)	0.73161 (15)	0.1110 (11)
F20	0.3620 (2)	0.7875 (2)	0.61389 (16)	0.1226 (13)
C1	0.1312 (2)	0.1966 (3)	0.1667 (2)	0.0594 (11)
H1	0.1044	0.2542	0.1492	0.071*
C2	0.1126 (3)	0.0879 (4)	0.1518 (2)	0.0715 (13)
H2	0.0739	0.0728	0.1246	0.086*
C3	0.1520 (3)	0.0048 (4)	0.1776 (2)	0.0663 (13)
C4	0.2094 (3)	0.0272 (3)	0.2170 (2)	0.0588 (12)
C5	0.2287 (2)	0.1334 (3)	0.23187 (18)	0.0511 (10)
H5	0.2682	0.1469	0.2584	0.061*
C6	0.1890 (2)	0.2208 (3)	0.20719 (17)	0.0454 (9)
C7	0.20746 (19)	0.3362 (3)	0.22500 (17)	0.0439 (9)
C8	0.2463 (2)	0.3721 (3)	0.27638 (18)	0.0449 (9)
H8	0.2676	0.3243	0.3057	0.054*
C9	0.25129 (19)	0.4888 (3)	0.28131 (16)	0.0412 (9)
C10	0.2160 (2)	0.5422 (3)	0.23176 (17)	0.0469 (10)
C11	0.2116 (3)	0.6637 (3)	0.2162 (2)	0.0632 (12)
H11A	0.1709	0.6949	0.2333	0.095*
H11B	0.2082	0.6729	0.1718	0.095*
H11C	0.2528	0.7005	0.2337	0.095*
C12	0.28788 (18)	0.5444 (3)	0.33468 (16)	0.0379 (8)
C13	0.3571 (2)	0.5005 (3)	0.36142 (18)	0.0469 (10)
C14	0.3876 (2)	0.5935 (3)	0.40342 (18)	0.0482 (10)
C15	0.3225 (2)	0.6572 (3)	0.4199 (2)	0.0518 (10)
C16	0.26703 (18)	0.6294 (3)	0.36903 (17)	0.0384 (9)
C17	0.19904 (18)	0.6874 (3)	0.36520 (16)	0.0374 (8)
C18	0.1360 (2)	0.6339 (3)	0.36691 (18)	0.0468 (10)
C19	0.1204 (2)	0.5126 (3)	0.3753 (2)	0.0642 (12)
H19A	0.1122	0.4783	0.3353	0.096*
H19B	0.0795	0.5046	0.3984	0.096*
H19C	0.1596	0.4777	0.3976	0.096*
C20	0.19152 (19)	0.8048 (3)	0.35822 (17)	0.0411 (9)
H20	0.2293	0.8530	0.3574	0.049*
C21	0.12326 (19)	0.8387 (3)	0.35284 (17)	0.0415 (9)
C22	0.0951 (2)	0.9508 (3)	0.34131 (17)	0.0429 (9)
C23	0.1350 (2)	1.0433 (3)	0.36040 (17)	0.0472 (10)
H23	0.1788	1.0341	0.3813	0.057*
C24	0.1095 (2)	1.1469 (3)	0.3483 (2)	0.0558 (11)
C25	0.0454 (3)	1.1634 (4)	0.3169 (2)	0.0658 (13)
C26	0.0058 (3)	1.0752 (4)	0.2976 (2)	0.0763 (14)
H26	−0.0375	1.0860	0.2762	0.092*
C27	0.0302 (2)	0.9684 (4)	0.3102 (2)	0.0613 (12)
H27	0.0026	0.9081	0.2975	0.074*
C28	0.0705 (2)	−0.1091 (4)	0.5356 (2)	0.0719 (13)
H28	0.0489	−0.0404	0.5377	0.086*
C29	0.0306 (3)	−0.2046 (5)	0.5412 (2)	0.0836 (16)
H29	−0.0170	−0.1997	0.5471	0.100*
C30	0.0621 (3)	−0.3048 (5)	0.5378 (2)	0.0797 (15)
C31	0.1321 (3)	−0.3116 (4)	0.5308 (2)	0.0695 (13)
C32	0.1724 (2)	−0.2193 (4)	0.52584 (19)	0.0592 (11)
H32	0.2203	−0.2263	0.5218	0.071*
C33	0.1420 (2)	−0.1143 (3)	0.52681 (17)	0.0496 (10)
C34	0.1844 (2)	−0.0150 (3)	0.51817 (17)	0.0467 (10)
C35	0.2526 (2)	−0.0067 (3)	0.50376 (17)	0.0471 (10)
H35	0.2807	−0.0680	0.4978	0.057*
C36	0.27720 (19)	0.1037 (3)	0.49863 (17)	0.0447 (9)
C37	0.2269 (2)	0.1805 (3)	0.50944 (18)	0.0485 (10)
C38	0.2309 (2)	0.3043 (3)	0.5086 (2)	0.0688 (13)
H38A	0.2492	0.3303	0.5486	0.103*
H38B	0.1850	0.3344	0.4995	0.103*
H38C	0.2613	0.3274	0.4773	0.103*
C39	0.3481 (2)	0.1317 (3)	0.47972 (18)	0.0445 (9)
C40	0.3701 (2)	0.0926 (3)	0.4180 (2)	0.0551 (11)
C41	0.4428 (3)	0.1371 (4)	0.4126 (2)	0.0695 (13)
C42	0.4608 (2)	0.2047 (3)	0.4711 (2)	0.0530 (11)
C43	0.3977 (2)	0.1931 (3)	0.50916 (18)	0.0452 (9)
C44	0.3973 (2)	0.2466 (3)	0.57065 (19)	0.0470 (10)
C45	0.3895 (2)	0.1904 (3)	0.62520 (19)	0.0492 (10)
C46	0.3795 (3)	0.0686 (3)	0.6363 (2)	0.0676 (13)
H46A	0.3308	0.0535	0.6402	0.101*
H46B	0.4059	0.0473	0.6740	0.101*
H46C	0.3957	0.0275	0.6020	0.101*
C47	0.4047 (2)	0.3627 (3)	0.58013 (19)	0.0501 (10)
H47	0.4107	0.4120	0.5478	0.060*
C48	0.4024 (2)	0.3954 (3)	0.64001 (18)	0.0482 (10)
C49	0.4052 (2)	0.5084 (3)	0.66511 (19)	0.0524 (10)
C50	0.4280 (2)	0.5314 (4)	0.7261 (2)	0.0685 (13)
H50	0.4432	0.4739	0.7523	0.082*
C51	0.4287 (3)	0.6393 (4)	0.7490 (2)	0.0823 (15)
H51	0.4439	0.6535	0.7902	0.099*
C52	0.4071 (3)	0.7232 (4)	0.7108 (3)	0.0758 (14)
C53	0.3846 (3)	0.7016 (4)	0.6508 (2)	0.0737 (14)
C54	0.3829 (3)	0.5966 (4)	0.6280 (2)	0.0663 (13)
H54	0.3665	0.5840	0.5869	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0753 (8)	0.0454 (6)	0.0436 (6)	−0.0007 (5)	−0.0101 (5)	−0.0032 (5)
S2	0.0414 (6)	0.0479 (6)	0.0741 (8)	0.0005 (5)	0.0016 (5)	0.0049 (5)
S3	0.0706 (7)	0.0572 (7)	0.0483 (6)	0.0069 (6)	0.0097 (5)	0.0017 (5)
S4	0.0519 (6)	0.0615 (7)	0.0512 (6)	0.0141 (5)	0.0054 (5)	0.0028 (5)
F1	0.135 (3)	0.0449 (16)	0.116 (2)	−0.0246 (17)	−0.008 (2)	−0.0131 (15)
F2	0.131 (3)	0.0644 (19)	0.114 (3)	0.0074 (18)	0.005 (2)	0.0071 (17)
F3	0.0547 (15)	0.0872 (19)	0.0723 (17)	0.0194 (13)	0.0076 (13)	−0.0166 (14)
F4	0.0744 (17)	0.0409 (13)	0.0803 (17)	0.0058 (12)	−0.0155 (13)	0.0148 (12)
F5	0.0571 (15)	0.0736 (17)	0.0878 (19)	−0.0166 (13)	0.0046 (13)	0.0092 (14)
F6	0.0633 (16)	0.0712 (16)	0.0679 (16)	0.0112 (13)	−0.0241 (13)	0.0006 (13)
F7	0.0773 (19)	0.0481 (15)	0.144 (3)	0.0080 (13)	−0.0450 (18)	−0.0342 (16)
F8	0.0709 (17)	0.133 (3)	0.0452 (16)	0.0219 (17)	−0.0023 (13)	−0.0082 (15)
F9	0.117 (2)	0.0488 (16)	0.097 (2)	−0.0084 (15)	−0.0052 (18)	0.0005 (14)
F10	0.125 (3)	0.0560 (17)	0.125 (3)	0.0341 (17)	−0.012 (2)	0.0197 (17)
F11	0.114 (3)	0.119 (3)	0.135 (3)	−0.063 (2)	0.015 (2)	0.012 (2)
F12	0.134 (3)	0.062 (2)	0.157 (3)	−0.0115 (19)	0.063 (2)	−0.0015 (19)
F13	0.100 (2)	0.246 (5)	0.0549 (19)	0.040 (3)	−0.0095 (17)	0.000 (2)
F14	0.185 (4)	0.065 (2)	0.147 (3)	−0.048 (2)	0.100 (3)	−0.057 (2)
F15	0.253 (5)	0.203 (4)	0.062 (2)	−0.151 (4)	0.030 (3)	−0.013 (2)
F16	0.084 (2)	0.166 (4)	0.310 (6)	0.021 (2)	0.028 (3)	−0.157 (4)
F17	0.0829 (18)	0.0573 (16)	0.0776 (18)	−0.0159 (13)	0.0200 (14)	−0.0014 (13)
F18	0.0550 (16)	0.138 (3)	0.090 (2)	0.0322 (17)	0.0036 (15)	0.0217 (19)
F19	0.169 (3)	0.0599 (18)	0.104 (2)	−0.011 (2)	0.014 (2)	−0.0344 (17)
F20	0.214 (4)	0.0571 (19)	0.095 (2)	0.011 (2)	0.002 (2)	0.0048 (17)
C1	0.061 (3)	0.043 (2)	0.072 (3)	−0.005 (2)	−0.005 (2)	−0.006 (2)
C2	0.077 (3)	0.053 (3)	0.084 (4)	−0.010 (3)	0.000 (3)	−0.008 (3)
C3	0.090 (4)	0.039 (3)	0.071 (3)	−0.019 (3)	0.008 (3)	−0.011 (2)
C4	0.084 (3)	0.035 (2)	0.058 (3)	0.008 (2)	0.012 (3)	0.006 (2)
C5	0.059 (3)	0.045 (2)	0.050 (2)	−0.001 (2)	0.006 (2)	−0.0056 (19)
C6	0.052 (2)	0.044 (2)	0.042 (2)	−0.0027 (19)	0.0090 (19)	−0.0066 (18)
C7	0.047 (2)	0.039 (2)	0.046 (2)	−0.0041 (18)	0.0043 (19)	−0.0071 (17)
C8	0.052 (2)	0.036 (2)	0.047 (2)	0.0035 (18)	0.0008 (19)	0.0003 (17)
C9	0.048 (2)	0.035 (2)	0.041 (2)	0.0021 (17)	0.0024 (18)	−0.0032 (16)
C10	0.057 (3)	0.042 (2)	0.041 (2)	−0.0002 (19)	0.0013 (19)	−0.0019 (18)
C11	0.095 (4)	0.041 (2)	0.052 (3)	0.001 (2)	−0.007 (2)	0.008 (2)
C12	0.042 (2)	0.0291 (19)	0.042 (2)	−0.0028 (16)	−0.0018 (17)	0.0023 (16)
C13	0.051 (2)	0.039 (2)	0.050 (2)	0.0074 (19)	0.002 (2)	0.0045 (19)
C14	0.043 (2)	0.049 (2)	0.052 (3)	−0.001 (2)	−0.007 (2)	0.0059 (19)
C15	0.055 (3)	0.039 (2)	0.059 (3)	0.002 (2)	−0.011 (2)	−0.007 (2)
C16	0.038 (2)	0.034 (2)	0.043 (2)	−0.0013 (17)	0.0005 (17)	0.0008 (16)
C17	0.040 (2)	0.035 (2)	0.037 (2)	0.0035 (17)	−0.0022 (16)	−0.0018 (16)
C18	0.047 (2)	0.037 (2)	0.056 (3)	0.0014 (18)	0.0019 (19)	0.0017 (18)
C19	0.061 (3)	0.042 (2)	0.090 (3)	−0.006 (2)	0.003 (2)	0.009 (2)
C20	0.041 (2)	0.035 (2)	0.047 (2)	−0.0027 (17)	0.0006 (17)	−0.0049 (16)
C21	0.044 (2)	0.037 (2)	0.043 (2)	0.0030 (17)	0.0006 (17)	−0.0015 (16)
C22	0.046 (2)	0.042 (2)	0.042 (2)	0.0061 (18)	0.0030 (18)	0.0007 (17)
C23	0.053 (2)	0.044 (2)	0.044 (2)	0.008 (2)	0.0003 (19)	0.0031 (18)
C24	0.079 (3)	0.037 (2)	0.052 (3)	−0.001 (2)	0.006 (2)	0.0019 (19)
C25	0.083 (3)	0.046 (3)	0.069 (3)	0.023 (3)	0.002 (3)	0.013 (2)
C26	0.067 (3)	0.065 (3)	0.093 (4)	0.019 (3)	−0.016 (3)	0.010 (3)
C27	0.056 (3)	0.052 (3)	0.074 (3)	0.006 (2)	−0.011 (2)	0.001 (2)
C28	0.051 (3)	0.087 (4)	0.078 (3)	0.006 (3)	0.003 (2)	0.018 (3)
C29	0.055 (3)	0.113 (5)	0.082 (4)	−0.016 (3)	0.003 (3)	0.024 (3)
C30	0.084 (4)	0.086 (4)	0.069 (3)	−0.033 (3)	0.007 (3)	0.006 (3)
C31	0.087 (4)	0.056 (3)	0.068 (3)	−0.006 (3)	0.023 (3)	0.000 (2)
C32	0.064 (3)	0.058 (3)	0.057 (3)	−0.008 (2)	0.019 (2)	−0.004 (2)
C33	0.051 (3)	0.061 (3)	0.036 (2)	−0.002 (2)	0.0022 (18)	0.0005 (19)
C34	0.053 (3)	0.050 (2)	0.037 (2)	0.003 (2)	−0.0005 (18)	0.0014 (17)
C35	0.049 (2)	0.044 (2)	0.048 (2)	0.0061 (19)	−0.0016 (19)	−0.0045 (18)
C36	0.045 (2)	0.042 (2)	0.046 (2)	0.0038 (19)	−0.0008 (18)	−0.0055 (18)
C37	0.054 (2)	0.045 (2)	0.045 (2)	0.006 (2)	0.0001 (19)	−0.0009 (18)
C38	0.078 (3)	0.050 (3)	0.079 (3)	0.011 (2)	0.006 (3)	0.001 (2)
C39	0.048 (2)	0.037 (2)	0.049 (2)	0.0088 (19)	0.0025 (19)	0.0007 (18)
C40	0.064 (3)	0.048 (3)	0.054 (3)	0.000 (2)	0.006 (2)	−0.009 (2)
C41	0.082 (4)	0.064 (3)	0.066 (3)	−0.001 (3)	0.029 (3)	−0.012 (2)
C42	0.053 (3)	0.046 (3)	0.060 (3)	0.005 (2)	0.000 (2)	0.004 (2)
C43	0.046 (2)	0.039 (2)	0.050 (2)	0.0051 (19)	0.0019 (19)	0.0010 (18)
C44	0.041 (2)	0.046 (2)	0.053 (3)	0.0015 (18)	−0.0010 (18)	−0.0053 (19)
C45	0.047 (2)	0.046 (2)	0.055 (3)	0.0057 (19)	0.0030 (19)	0.0033 (19)
C46	0.076 (3)	0.054 (3)	0.074 (3)	0.012 (2)	0.016 (3)	0.008 (2)
C47	0.054 (3)	0.048 (2)	0.048 (2)	−0.007 (2)	0.002 (2)	0.0009 (19)
C48	0.049 (2)	0.051 (2)	0.044 (2)	0.000 (2)	0.0015 (19)	−0.0023 (19)
C49	0.055 (3)	0.054 (3)	0.049 (3)	−0.002 (2)	0.001 (2)	−0.008 (2)
C50	0.080 (3)	0.064 (3)	0.059 (3)	0.005 (3)	−0.006 (2)	−0.006 (2)
C51	0.104 (4)	0.077 (4)	0.065 (3)	−0.009 (3)	−0.008 (3)	−0.030 (3)
C52	0.098 (4)	0.055 (3)	0.075 (4)	−0.008 (3)	0.014 (3)	−0.022 (3)
C53	0.105 (4)	0.047 (3)	0.070 (3)	0.000 (3)	0.013 (3)	−0.005 (3)
C54	0.091 (4)	0.058 (3)	0.049 (3)	−0.002 (3)	0.002 (2)	−0.009 (2)

Geometric parameters (Å, º)

S1—C10	1.710 (4)	C19—H19B	0.9600
S1—C7	1.720 (4)	C19—H19C	0.9600
S2—C21	1.724 (4)	C20—C21	1.366 (5)
S2—C18	1.724 (4)	C20—H20	0.9300
S3—C45	1.720 (4)	C21—C22	1.475 (5)
S3—C48	1.728 (4)	C22—C27	1.387 (5)
S4—C37	1.722 (4)	C22—C23	1.400 (5)
S4—C34	1.732 (4)	C23—C24	1.364 (5)
F1—C3	1.353 (5)	C23—H23	0.9300
F2—C4	1.345 (5)	C24—C25	1.373 (6)
F3—C13	1.349 (4)	C25—C26	1.357 (6)
F4—C13	1.364 (4)	C26—C27	1.395 (6)
F5—C14	1.353 (4)	C26—H26	0.9300
F6—C14	1.341 (4)	C27—H27	0.9300
F7—C15	1.336 (4)	C28—C29	1.394 (7)
F8—C15	1.369 (5)	C28—C33	1.395 (6)
F9—C24	1.348 (5)	C28—H28	0.9300
F10—C25	1.353 (5)	C29—C30	1.358 (7)
F11—C30	1.352 (5)	C29—H29	0.9300
F12—C31	1.339 (5)	C30—C31	1.359 (7)
F13—C40	1.351 (5)	C31—C32	1.365 (6)
F14—C40	1.308 (5)	C32—C33	1.397 (6)
F15—C41	1.308 (6)	C32—H32	0.9300
F16—C41	1.310 (6)	C33—C34	1.468 (5)
F17—C42	1.347 (4)	C34—C35	1.366 (5)
F18—C42	1.335 (5)	C35—C36	1.422 (5)
F19—C52	1.348 (5)	C35—H35	0.9300
F20—C53	1.360 (5)	C36—C37	1.369 (5)
C1—C6	1.393 (5)	C36—C39	1.482 (5)
C1—C2	1.393 (6)	C37—C38	1.500 (5)
C1—H1	0.9300	C38—H38A	0.9600
C2—C3	1.352 (6)	C38—H38B	0.9600
C2—H2	0.9300	C38—H38C	0.9600
C3—C4	1.370 (6)	C39—C43	1.331 (5)
C4—C5	1.368 (5)	C39—C40	1.497 (5)
C5—C6	1.386 (5)	C40—C41	1.502 (6)
C5—H5	0.9300	C41—C42	1.523 (6)
C6—C7	1.483 (5)	C42—C43	1.509 (5)
C7—C8	1.361 (5)	C43—C44	1.474 (5)
C8—C9	1.420 (5)	C44—C45	1.374 (5)
C8—H8	0.9300	C44—C47	1.426 (5)
C9—C10	1.383 (5)	C45—C46	1.507 (5)
C9—C12	1.468 (5)	C46—H46A	0.9600
C10—C11	1.509 (5)	C46—H46B	0.9600
C11—H11A	0.9600	C46—H46C	0.9600
C11—H11B	0.9600	C47—C48	1.352 (5)
C11—H11C	0.9600	C47—H47	0.9300
C12—C16	1.343 (5)	C48—C49	1.470 (5)
C12—C13	1.505 (5)	C49—C54	1.383 (6)
C13—C14	1.532 (5)	C49—C50	1.385 (6)
C14—C15	1.525 (5)	C50—C51	1.395 (6)
C15—C16	1.510 (5)	C50—H50	0.9300
C16—C17	1.475 (5)	C51—C52	1.353 (7)
C17—C18	1.372 (5)	C51—H51	0.9300
C17—C20	1.433 (5)	C52—C53	1.359 (7)
C18—C19	1.511 (5)	C53—C54	1.362 (6)
C19—H19A	0.9600	C54—H54	0.9300
C10—S1—C7	93.64 (18)	C22—C27—H27	119.6
C21—S2—C18	93.18 (18)	C26—C27—H27	119.6
C45—S3—C48	93.44 (19)	C29—C28—C33	121.4 (5)
C37—S4—C34	93.37 (19)	C29—C28—H28	119.3
C6—C1—C2	121.5 (4)	C33—C28—H28	119.3
C6—C1—H1	119.3	C30—C29—C28	119.3 (5)
C2—C1—H1	119.3	C30—C29—H29	120.4
C3—C2—C1	118.8 (4)	C28—C29—H29	120.4
C3—C2—H2	120.6	F11—C30—C29	119.8 (5)
C1—C2—H2	120.6	F11—C30—C31	120.0 (6)
C2—C3—F1	120.6 (5)	C29—C30—C31	120.2 (5)
C2—C3—C4	120.5 (4)	F12—C31—C30	118.0 (5)
F1—C3—C4	118.9 (4)	F12—C31—C32	120.4 (5)
F2—C4—C5	120.2 (4)	C30—C31—C32	121.6 (5)
F2—C4—C3	118.3 (4)	C31—C32—C33	120.3 (4)
C5—C4—C3	121.5 (4)	C31—C32—H32	119.8
C4—C5—C6	119.7 (4)	C33—C32—H32	119.8
C4—C5—H5	120.2	C28—C33—C32	117.1 (4)
C6—C5—H5	120.2	C28—C33—C34	122.3 (4)
C5—C6—C1	118.0 (4)	C32—C33—C34	120.5 (4)
C5—C6—C7	120.3 (3)	C35—C34—C33	129.3 (4)
C1—C6—C7	121.7 (4)	C35—C34—S4	109.2 (3)
C8—C7—C6	128.1 (3)	C33—C34—S4	121.5 (3)
C8—C7—S1	109.7 (3)	C34—C35—C36	114.4 (4)
C6—C7—S1	122.1 (3)	C34—C35—H35	122.8
C7—C8—C9	114.1 (3)	C36—C35—H35	122.8
C7—C8—H8	122.9	C37—C36—C35	112.6 (3)
C9—C8—H8	122.9	C37—C36—C39	124.0 (3)
C10—C9—C8	112.3 (3)	C35—C36—C39	123.3 (3)
C10—C9—C12	124.9 (3)	C36—C37—C38	129.7 (4)
C8—C9—C12	122.7 (3)	C36—C37—S4	110.4 (3)
C9—C10—C11	130.0 (3)	C38—C37—S4	119.9 (3)
C9—C10—S1	110.2 (3)	C37—C38—H38A	109.5
C11—C10—S1	119.7 (3)	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	129.3 (4)
H11B—C11—H11C	109.5	C43—C39—C40	111.4 (3)
C16—C12—C9	129.7 (3)	C36—C39—C40	119.2 (3)
C16—C12—C13	110.2 (3)	F14—C40—F13	106.2 (4)
C9—C12—C13	119.9 (3)	F14—C40—C39	114.2 (4)
F3—C13—F4	106.1 (3)	F13—C40—C39	110.2 (4)
F3—C13—C12	114.2 (3)	F14—C40—C41	111.7 (4)
F4—C13—C12	110.5 (3)	F13—C40—C41	108.7 (4)
F3—C13—C14	112.2 (3)	C39—C40—C41	105.8 (3)
F4—C13—C14	108.9 (3)	F15—C41—F16	106.1 (5)
C12—C13—C14	104.8 (3)	F15—C41—C40	111.9 (5)
F6—C14—F5	107.3 (3)	F16—C41—C40	109.3 (4)
F6—C14—C15	113.5 (3)	F15—C41—C42	111.8 (4)
F5—C14—C15	109.4 (3)	F16—C41—C42	111.0 (4)
F6—C14—C13	113.9 (3)	C40—C41—C42	106.7 (4)
F5—C14—C13	109.7 (3)	F18—C42—F17	105.6 (3)
C15—C14—C13	103.0 (3)	F18—C42—C43	112.2 (3)
F7—C15—F8	105.5 (3)	F17—C42—C43	113.1 (3)
F7—C15—C16	113.7 (3)	F18—C42—C41	111.4 (4)
F8—C15—C16	110.4 (3)	F17—C42—C41	109.9 (4)
F7—C15—C14	112.8 (3)	C43—C42—C41	104.7 (3)
F8—C15—C14	109.2 (3)	C39—C43—C44	128.7 (4)
C16—C15—C14	105.3 (3)	C39—C43—C42	111.3 (3)
C12—C16—C17	128.8 (3)	C44—C43—C42	120.0 (3)
C12—C16—C15	110.4 (3)	C45—C44—C47	112.4 (4)
C17—C16—C15	120.6 (3)	C45—C44—C43	123.9 (3)
C18—C17—C20	112.8 (3)	C47—C44—C43	123.7 (4)
C18—C17—C16	123.2 (3)	C44—C45—C46	129.9 (4)
C20—C17—C16	124.0 (3)	C44—C45—S3	110.1 (3)
C17—C18—C19	130.0 (3)	C46—C45—S3	120.0 (3)
C17—C18—S2	110.3 (3)	C45—C46—H46A	109.5
C19—C18—S2	119.7 (3)	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	114.5 (4)
H19B—C19—H19C	109.5	C48—C47—H47	122.7
C21—C20—C17	113.3 (3)	C44—C47—H47	122.7
C21—C20—H20	123.4	C47—C48—C49	128.3 (4)
C17—C20—H20	123.4	C47—C48—S3	109.5 (3)
C20—C21—C22	128.8 (3)	C49—C48—S3	122.1 (3)
C20—C21—S2	110.3 (3)	C54—C49—C50	117.3 (4)
C22—C21—S2	120.8 (3)	C54—C49—C48	120.2 (4)
C27—C22—C23	118.2 (4)	C50—C49—C48	122.5 (4)
C27—C22—C21	121.8 (4)	C49—C50—C51	121.2 (5)
C23—C22—C21	120.0 (3)	C49—C50—H50	119.4
C24—C23—C22	119.8 (4)	C51—C50—H50	119.4
C24—C23—H23	120.1	C52—C51—C50	119.4 (5)
C22—C23—H23	120.1	C52—C51—H51	120.3
F9—C24—C23	120.4 (4)	C50—C51—H51	120.3
F9—C24—C25	118.1 (4)	F19—C52—C51	120.7 (5)
C23—C24—C25	121.6 (4)	F19—C52—C53	119.4 (5)
F10—C25—C26	120.9 (4)	C51—C52—C53	119.9 (4)
F10—C25—C24	119.2 (4)	C52—C53—F20	118.5 (4)
C26—C25—C24	119.8 (4)	C52—C53—C54	121.3 (5)
C25—C26—C27	119.8 (4)	F20—C53—C54	120.2 (5)
C25—C26—H26	120.1	C53—C54—C49	120.8 (4)
C27—C26—H26	120.1	C53—C54—H54	119.6
C22—C27—C26	120.8 (4)	C49—C54—H54	119.6
C6—C1—C2—C3	0.1 (7)	C33—C28—C29—C30	−0.2 (8)
C1—C2—C3—F1	177.6 (4)	C28—C29—C30—F11	−179.2 (4)
C1—C2—C3—C4	−0.8 (7)	C28—C29—C30—C31	1.7 (8)
C2—C3—C4—F2	180.0 (4)	F11—C30—C31—F12	−0.8 (7)
F1—C3—C4—F2	1.6 (7)	C29—C30—C31—F12	178.3 (5)
C2—C3—C4—C5	0.4 (7)	F11—C30—C31—C32	179.8 (4)
F1—C3—C4—C5	−178.0 (4)	C29—C30—C31—C32	−1.1 (8)
F2—C4—C5—C6	−178.9 (4)	F12—C31—C32—C33	179.5 (4)
C3—C4—C5—C6	0.7 (6)	C30—C31—C32—C33	−1.1 (7)
C4—C5—C6—C1	−1.3 (6)	C29—C28—C33—C32	−1.9 (7)
C4—C5—C6—C7	177.3 (4)	C29—C28—C33—C34	177.4 (4)
C2—C1—C6—C5	1.0 (6)	C31—C32—C33—C28	2.6 (6)
C2—C1—C6—C7	−177.7 (4)	C31—C32—C33—C34	−176.7 (4)
C5—C6—C7—C8	−21.1 (6)	C28—C33—C34—C35	−173.6 (4)
C1—C6—C7—C8	157.5 (4)	C32—C33—C34—C35	5.7 (6)
C5—C6—C7—S1	161.1 (3)	C28—C33—C34—S4	5.7 (5)
C1—C6—C7—S1	−20.3 (5)	C32—C33—C34—S4	−175.0 (3)
C10—S1—C7—C8	−0.8 (3)	C37—S4—C34—C35	−0.6 (3)
C10—S1—C7—C6	177.3 (3)	C37—S4—C34—C33	180.0 (3)
C6—C7—C8—C9	−176.9 (4)	C33—C34—C35—C36	179.7 (4)
S1—C7—C8—C9	1.0 (4)	S4—C34—C35—C36	0.4 (4)
C7—C8—C9—C10	−0.8 (5)	C34—C35—C36—C37	0.1 (5)
C7—C8—C9—C12	177.0 (3)	C34—C35—C36—C39	−176.2 (3)
C8—C9—C10—C11	−175.6 (4)	C35—C36—C37—C38	−179.9 (4)
C12—C9—C10—C11	6.6 (7)	C39—C36—C37—C38	−3.6 (7)
C8—C9—C10—S1	0.2 (4)	C35—C36—C37—S4	−0.6 (4)
C12—C9—C10—S1	−177.6 (3)	C39—C36—C37—S4	175.7 (3)
C7—S1—C10—C9	0.3 (3)	C34—S4—C37—C36	0.7 (3)
C7—S1—C10—C11	176.6 (3)	C34—S4—C37—C38	−179.9 (3)
C10—C9—C12—C16	45.1 (6)	C37—C36—C39—C43	59.4 (6)
C8—C9—C12—C16	−132.4 (4)	C35—C36—C39—C43	−124.6 (4)
C10—C9—C12—C13	−140.1 (4)	C37—C36—C39—C40	−117.6 (4)
C8—C9—C12—C13	42.4 (5)	C35—C36—C39—C40	58.4 (5)
C16—C12—C13—F3	−141.7 (3)	C43—C39—C40—F14	124.3 (4)
C9—C12—C13—F3	42.6 (5)	C36—C39—C40—F14	−58.3 (5)
C16—C12—C13—F4	98.7 (4)	C43—C39—C40—F13	−116.4 (4)
C9—C12—C13—F4	−77.0 (4)	C36—C39—C40—F13	61.1 (5)
C16—C12—C13—C14	−18.5 (4)	C43—C39—C40—C41	1.0 (5)
C9—C12—C13—C14	165.8 (3)	C36—C39—C40—C41	178.5 (4)
F3—C13—C14—F6	−87.7 (4)	F14—C40—C41—F15	110.8 (5)
F4—C13—C14—F6	29.5 (4)	F13—C40—C41—F15	−6.0 (5)
C12—C13—C14—F6	147.8 (3)	C39—C40—C41—F15	−124.3 (4)
F3—C13—C14—F5	32.6 (4)	F14—C40—C41—F16	−6.4 (6)
F4—C13—C14—F5	149.8 (3)	F13—C40—C41—F16	−123.3 (5)
C12—C13—C14—F5	−91.9 (4)	C39—C40—C41—F16	118.4 (5)
F3—C13—C14—C15	149.0 (3)	F14—C40—C41—C42	−126.5 (4)
F4—C13—C14—C15	−93.9 (4)	F13—C40—C41—C42	116.6 (4)
C12—C13—C14—C15	24.5 (4)	C39—C40—C41—C42	−1.7 (5)
F6—C14—C15—F7	89.7 (4)	F15—C41—C42—F18	−114.0 (5)
F5—C14—C15—F7	−30.1 (5)	F16—C41—C42—F18	4.3 (6)
C13—C14—C15—F7	−146.7 (3)	C40—C41—C42—F18	123.3 (4)
F6—C14—C15—F8	−27.3 (4)	F15—C41—C42—F17	2.7 (6)
F5—C14—C15—F8	−147.1 (3)	F16—C41—C42—F17	121.0 (5)
C13—C14—C15—F8	96.3 (3)	C40—C41—C42—F17	−120.0 (4)
F6—C14—C15—C16	−145.9 (3)	F15—C41—C42—C43	124.5 (5)
F5—C14—C15—C16	94.4 (4)	F16—C41—C42—C43	−117.2 (4)
C13—C14—C15—C16	−22.2 (4)	C40—C41—C42—C43	1.8 (5)
C9—C12—C16—C17	4.1 (6)	C36—C39—C43—C44	3.2 (7)
C13—C12—C16—C17	−171.1 (3)	C40—C39—C43—C44	−179.7 (4)
C9—C12—C16—C15	179.3 (4)	C36—C39—C43—C42	−177.0 (4)
C13—C12—C16—C15	4.1 (4)	C40—C39—C43—C42	0.2 (5)
F7—C15—C16—C12	136.0 (4)	F18—C42—C43—C39	−122.2 (4)
F8—C15—C16—C12	−105.7 (4)	F17—C42—C43—C39	118.4 (4)
C14—C15—C16—C12	12.0 (4)	C41—C42—C43—C39	−1.2 (5)
F7—C15—C16—C17	−48.3 (5)	F18—C42—C43—C44	57.6 (5)
F8—C15—C16—C17	70.0 (4)	F17—C42—C43—C44	−61.8 (5)
C14—C15—C16—C17	−172.3 (3)	C41—C42—C43—C44	178.6 (4)
C12—C16—C17—C18	52.6 (6)	C39—C43—C44—C45	59.1 (6)
C15—C16—C17—C18	−122.1 (4)	C42—C43—C44—C45	−120.8 (4)
C12—C16—C17—C20	−126.2 (4)	C39—C43—C44—C47	−120.8 (5)
C15—C16—C17—C20	59.0 (5)	C42—C43—C44—C47	59.4 (5)
C20—C17—C18—C19	−178.2 (4)	C47—C44—C45—C46	179.5 (4)
C16—C17—C18—C19	2.8 (6)	C43—C44—C45—C46	−0.4 (7)
C20—C17—C18—S2	0.8 (4)	C47—C44—C45—S3	−0.9 (4)
C16—C17—C18—S2	−178.2 (3)	C43—C44—C45—S3	179.2 (3)
C21—S2—C18—C17	0.3 (3)	C48—S3—C45—C44	1.4 (3)
C21—S2—C18—C19	179.4 (3)	C48—S3—C45—C46	−178.9 (3)
C18—C17—C20—C21	−1.9 (5)	C45—C44—C47—C48	−0.3 (5)
C16—C17—C20—C21	177.1 (3)	C43—C44—C47—C48	179.6 (4)
C17—C20—C21—C22	−176.0 (3)	C44—C47—C48—C49	−176.9 (4)
C17—C20—C21—S2	2.0 (4)	C44—C47—C48—S3	1.3 (4)
C18—S2—C21—C20	−1.3 (3)	C45—S3—C48—C47	−1.6 (3)
C18—S2—C21—C22	176.8 (3)	C45—S3—C48—C49	176.8 (3)
C20—C21—C22—C27	150.4 (4)	C47—C48—C49—C54	26.1 (7)
S2—C21—C22—C27	−27.4 (5)	S3—C48—C49—C54	−151.9 (4)
C20—C21—C22—C23	−27.7 (6)	C47—C48—C49—C50	−155.4 (4)
S2—C21—C22—C23	154.5 (3)	S3—C48—C49—C50	26.5 (6)
C27—C22—C23—C24	0.1 (6)	C54—C49—C50—C51	−0.2 (7)
C21—C22—C23—C24	178.4 (4)	C48—C49—C50—C51	−178.7 (4)
C22—C23—C24—F9	179.6 (4)	C49—C50—C51—C52	−0.5 (8)
C22—C23—C24—C25	−0.8 (6)	C50—C51—C52—F19	−179.9 (5)
F9—C24—C25—F10	0.7 (6)	C50—C51—C52—C53	0.4 (8)
C23—C24—C25—F10	−179.0 (4)	F19—C52—C53—F20	−0.8 (8)
F9—C24—C25—C26	−179.8 (4)	C51—C52—C53—F20	178.9 (5)
C23—C24—C25—C26	0.5 (7)	F19—C52—C53—C54	−179.4 (5)
F10—C25—C26—C27	179.9 (4)	C51—C52—C53—C54	0.3 (9)
C24—C25—C26—C27	0.4 (8)	C52—C53—C54—C49	−1.0 (8)
C23—C22—C27—C26	0.7 (6)	F20—C53—C54—C49	−179.5 (4)
C21—C22—C27—C26	−177.5 (4)	C50—C49—C54—C53	0.9 (7)
C25—C26—C27—C22	−1.0 (8)	C48—C49—C54—C53	179.5 (4)