3,3,4,4,5,5-Hexa­fluoro-1-[2-methyl-5-(2-fluoro­phen­yl)-3-thien­yl]-2-(2-methyl-5-phenyl-3-thien­yl)cyclo­pent-1-ene, a new photochromic dithienylethene

The title compound, C₂₇H₁₇F₇S₂, a new unsymmetrical photochromic dithienylethene with an ortho-fluoro­phenyl substituent, is one of the most promising candidates for photoelectronic applications, such as optical storage, photoswitches and waveguides. There are two mol­ecules in the asymmetric unit. Both adopt a photoactive anti-parallel conformation. For one mol­ecule, the distance between the two reactive C atoms is 3.572 (6) Å; the dihedral angles between the central cyclo­pentene ring and the thio­phene rings are 49.7 (2) and 45.9 (2)°, and those between the thio­phene rings and the adjacent benzene rings are 8.1 (2) and 25.5 (1)°. For the other mol­ecule, the distance between the two reactive C atoms is 3.588 (6) Å; the dihedral angles between the central cyclo­pentene ring and the thio­phene rings are 43.7 (2) and 46.8 (2)°, and those between the thio­phene rings and the adjacent benzene rings are 27.5 (1) and 11.1 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.070
• wR factor = 0.145
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C30
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C32
PLAT431_ALERT_2_B Short Inter HL..A Contact  F5     ..  F7      ..       2.54 Ang.

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.30
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        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C38
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C49
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C21    -   C22    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C22    -   C23    ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C37    -   C38    ...       1.36 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C38    -   C39    ...       1.36 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C48    -   C49    ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C49    -   C50    ...       1.35 Ang.
PLAT731_ALERT_1_C Bond    Calc    1.349(7), Rep    1.349(3) ......       2.33 su-Rat
              F11  -C31     1.555   1.555

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

---

Computing details

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-[2-Methyl-5-(2-fluorophenyl)-3-thienyl]-2-(2-methyl-5-phenyl-3-thienyl)- 3,3,4,4,5,5-hexafluorocyclopent-1-ene

Crystal data

C27H17F7S2	Z = 4
Mr = 538.53	F(000) = 1096
Triclinic, P1	Dx = 1.472 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.8563 (15) Å	Cell parameters from 48 reflections
b = 13.7789 (18) Å	θ = 2.7–13.7°
c = 15.281 (2) Å	µ = 0.29 mm^−1
α = 81.368 (9)°	T = 295 K
β = 82.348 (9)°	Prism, blue
γ = 82.442 (9)°	0.6 × 0.5 × 0.4 mm
V = 2430.2 (6) Å^3

Data collection

Bruker P4 diffractometer	Rint = 0.020
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.9°
Graphite monochromator	h = −13→1
ω scans	k = −16→16
9883 measured reflections	l = −18→18
8533 independent reflections	3 standard reflections every 97 reflections
5559 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 4.5P] where P = (Fo^2 + 2Fc^2)/3
8533 reflections	(Δ/σ)max = 0.002
661 parameters	Δρmax = 1.04 e Å^−3
6 restraints	Δρmin = −0.45 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	Occ. (<1)
S1	0.42549 (11)	0.89928 (9)	0.93578 (8)	0.0730 (3)
S2	0.18056 (10)	0.86125 (9)	0.63947 (9)	0.0780 (4)
S3	0.54161 (11)	0.64446 (10)	0.86747 (10)	0.0830 (4)
S4	0.90344 (13)	0.60368 (10)	0.56489 (8)	0.0835 (4)
F1	0.3467 (3)	1.1998 (2)	0.5333 (2)	0.1138 (11)
F2	0.1789 (3)	1.2420 (2)	0.6015 (3)	0.1190 (12)
F3	0.2598 (3)	1.3203 (2)	0.7176 (2)	0.1039 (10)
F4	0.3897 (3)	1.3468 (2)	0.6054 (2)	0.0982 (9)
F5	0.4360 (3)	1.2418 (2)	0.7904 (2)	0.0979 (9)
F6	0.5297 (2)	1.1996 (2)	0.6690 (2)	0.0969 (9)
F7	0.5801 (12)	0.7938 (15)	1.0407 (13)	0.181 (3)	0.224 (9)
F8	−0.0335 (5)	0.7798 (4)	0.6942 (5)	0.181 (3)	0.776 (9)
F9	0.9559 (4)	0.2618 (2)	0.7110 (3)	0.1388 (15)
F10	0.9963 (3)	0.3030 (2)	0.8299 (3)	0.1260 (13)
F11	0.7906 (4)	0.1785 (3)	0.7798 (3)	0.1662 (18)
F12	0.8715 (3)	0.1588 (3)	0.8944 (3)	0.1546 (18)
F13	0.6310 (3)	0.2594 (2)	0.8726 (3)	0.1333 (14)
F14	0.7348 (4)	0.2979 (3)	0.9619 (2)	0.1531 (17)
F15	0.3248 (6)	0.7366 (5)	0.8174 (5)	0.148 (3)	0.590 (10)
F16	1.0706 (7)	0.6909 (7)	0.4595 (7)	0.148 (3)	0.410 (10)
C1	0.3746 (3)	1.1097 (3)	0.7320 (3)	0.0584 (10)
C2	0.2983 (3)	1.1086 (3)	0.6739 (3)	0.0606 (10)
C3	0.2861 (4)	1.2055 (4)	0.6153 (3)	0.0762 (13)
C4	0.3414 (4)	1.2758 (3)	0.6606 (3)	0.0745 (13)
C5	0.4243 (4)	1.2062 (3)	0.7158 (3)	0.0676 (11)
C6	0.3457 (4)	0.9776 (3)	0.8636 (3)	0.0634 (11)
C7	0.4139 (4)	1.0333 (3)	0.8023 (3)	0.0577 (10)
C8	0.5315 (4)	1.0116 (3)	0.8158 (3)	0.0623 (10)
H8A	0.5890	1.0439	0.7803	0.075*
C9	0.5527 (4)	0.9399 (3)	0.8848 (3)	0.0618 (10)
C10	0.6635 (4)	0.8979 (3)	0.9160 (3)	0.0676 (11)
C11	0.6708 (5)	0.8336 (4)	0.9951 (3)	0.0828 (14)
H11A	0.6013	0.8150	1.0295	0.099*	0.776 (9)
C12	0.7752 (6)	0.7974 (4)	1.0240 (4)	0.0935 (17)
H12A	0.7780	0.7555	1.0776	0.112*
C13	0.8743 (6)	0.8221 (5)	0.9752 (4)	0.106 (2)
H13A	0.9445	0.7959	0.9944	0.127*
C14	0.8699 (5)	0.8853 (5)	0.8979 (4)	0.1054 (19)
H14A	0.9376	0.9029	0.8648	0.126*
C15	0.7651 (4)	0.9243 (4)	0.8675 (4)	0.0883 (15)
H15A	0.7634	0.9679	0.8148	0.106*
C16	0.2176 (4)	0.9796 (4)	0.8766 (3)	0.0823 (14)
H16A	0.1833	1.0431	0.8520	0.123*
H16B	0.1917	0.9675	0.9391	0.123*
H16C	0.1959	0.9294	0.8469	0.123*
C17	0.2828 (4)	0.9343 (3)	0.6514 (3)	0.0686 (12)
C18	0.2346 (4)	1.0283 (3)	0.6613 (3)	0.0632 (11)
C19	0.1147 (4)	1.0405 (3)	0.6565 (3)	0.0672 (11)
H19A	0.0695	1.1005	0.6605	0.081*
C20	0.0719 (4)	0.9575 (3)	0.6457 (3)	0.0679 (11)
C21	−0.0468 (4)	0.9465 (4)	0.6344 (3)	0.0711 (12)
C22	−0.0931 (5)	0.8590 (4)	0.6533 (4)	0.0974 (18)
H22A	−0.0446	0.8017	0.6755	0.117*	0.224 (9)
C23	−0.2044 (5)	0.8475 (5)	0.6441 (5)	0.118 (2)
H23A	−0.2322	0.7864	0.6589	0.141*
C24	−0.2721 (5)	0.9297 (6)	0.6124 (4)	0.110 (2)
H24A	−0.3471	0.9243	0.6037	0.132*
C25	−0.2328 (5)	1.0173 (5)	0.5936 (4)	0.1008 (18)
H25A	−0.2818	1.0723	0.5739	0.121*
C26	−0.1195 (4)	1.0290 (4)	0.6026 (3)	0.0879 (15)
H26A	−0.0929	1.0906	0.5877	0.106*
C27	0.4064 (4)	0.8916 (4)	0.6472 (4)	0.0940 (17)
H27A	0.4543	0.9440	0.6308	0.141*
H27B	0.4222	0.8467	0.6037	0.141*
H27C	0.4217	0.8569	0.7045	0.141*
C28	0.7377 (4)	0.3957 (3)	0.8217 (3)	0.0613 (10)
C29	0.8368 (4)	0.3952 (3)	0.7675 (3)	0.0600 (10)
C30	0.9075 (4)	0.2977 (3)	0.7847 (3)	0.0751 (13)
C31	0.8270 (5)	0.2305 (3)	0.8366 (3)	0.0980 (17)
C32	0.7274 (4)	0.2970 (4)	0.8758 (3)	0.0744 (13)
C33	0.6677 (4)	0.5695 (3)	0.8502 (3)	0.0691 (12)
C34	0.6476 (3)	0.4777 (3)	0.8375 (3)	0.0623 (10)
C35	0.5278 (4)	0.4692 (3)	0.8429 (3)	0.0682 (11)
H35A	0.4996	0.4111	0.8365	0.082*
C36	0.4595 (4)	0.5526 (3)	0.8579 (3)	0.0682 (11)
C37	0.3336 (4)	0.5679 (4)	0.8678 (3)	0.0724 (12)
C38	0.2715 (4)	0.6573 (4)	0.8483 (4)	0.0872 (15)
H38A	0.3132	0.7131	0.8278	0.105*	0.410 (10)
C39	0.1554 (5)	0.6743 (5)	0.8560 (4)	0.1068 (19)
H39A	0.1181	0.7373	0.8417	0.128*
C40	0.0962 (5)	0.5960 (7)	0.8851 (4)	0.118 (2)
H40A	0.0166	0.6049	0.8909	0.142*
C41	0.1522 (5)	0.5035 (6)	0.9062 (4)	0.113 (2)
H41A	0.1096	0.4508	0.9264	0.136*
C42	0.2715 (4)	0.4867 (5)	0.8982 (4)	0.0976 (17)
H42A	0.3088	0.4237	0.9125	0.117*
C43	0.7794 (4)	0.6084 (4)	0.8534 (4)	0.0881 (16)
H43A	0.8325	0.5561	0.8782	0.132*
H43B	0.7670	0.6607	0.8899	0.132*
H43C	0.8101	0.6334	0.7942	0.132*
C44	0.8186 (4)	0.5281 (3)	0.6370 (3)	0.0702 (12)
C45	0.8814 (4)	0.4706 (3)	0.6989 (3)	0.0599 (10)
C46	0.9973 (4)	0.4893 (3)	0.6861 (3)	0.0650 (11)
H46A	1.0512	0.4559	0.7222	0.078*
C47	1.0239 (4)	0.5602 (3)	0.6166 (3)	0.0682 (12)
C48	1.1353 (5)	0.5970 (3)	0.5861 (3)	0.0775 (14)
C49	1.1583 (6)	0.6562 (4)	0.5059 (4)	0.0964 (17)
H49A	1.0959	0.6762	0.4707	0.116*	0.590 (10)
C50	1.2602 (7)	0.6891 (5)	0.4756 (4)	0.111 (2)
H50A	1.2701	0.7285	0.4208	0.134*
C51	1.3488 (7)	0.6640 (5)	0.5262 (5)	0.118 (2)
H51A	1.4198	0.6860	0.5063	0.142*
C52	1.3318 (5)	0.6064 (4)	0.6059 (5)	0.1073 (19)
H52A	1.3920	0.5894	0.6406	0.129*
C53	1.2262 (4)	0.5723 (4)	0.6372 (4)	0.0872 (15)
H53A	1.2166	0.5330	0.6921	0.105*
C54	0.6947 (4)	0.5319 (4)	0.6237 (3)	0.0903 (16)
H54A	0.6677	0.4696	0.6476	0.135*
H54B	0.6869	0.5455	0.5611	0.135*
H54C	0.6504	0.5832	0.6537	0.135*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0873 (8)	0.0617 (7)	0.0665 (7)	−0.0132 (6)	−0.0052 (6)	0.0028 (5)
S2	0.0600 (7)	0.0750 (8)	0.1047 (10)	−0.0017 (6)	−0.0155 (6)	−0.0301 (7)
S3	0.0610 (7)	0.0784 (8)	0.1160 (11)	−0.0073 (6)	−0.0059 (7)	−0.0382 (8)
S4	0.1071 (10)	0.0717 (8)	0.0662 (7)	−0.0012 (7)	−0.0157 (7)	0.0055 (6)
F1	0.156 (3)	0.114 (3)	0.0690 (19)	−0.026 (2)	−0.011 (2)	0.0023 (17)
F2	0.088 (2)	0.097 (2)	0.170 (3)	−0.0082 (17)	−0.064 (2)	0.029 (2)
F3	0.097 (2)	0.084 (2)	0.123 (3)	0.0106 (17)	−0.0027 (19)	−0.0163 (18)
F4	0.103 (2)	0.0754 (18)	0.109 (2)	−0.0217 (16)	−0.0183 (18)	0.0262 (16)
F5	0.130 (3)	0.0772 (18)	0.098 (2)	−0.0363 (17)	−0.0405 (19)	−0.0045 (16)
F6	0.0598 (16)	0.093 (2)	0.126 (2)	−0.0175 (14)	−0.0021 (16)	0.0249 (18)
F7	0.135 (5)	0.142 (5)	0.281 (8)	−0.036 (4)	−0.051 (5)	−0.037 (5)
F8	0.135 (5)	0.142 (5)	0.281 (8)	−0.036 (4)	−0.051 (5)	−0.037 (5)
F9	0.181 (4)	0.083 (2)	0.123 (3)	0.045 (2)	0.022 (3)	−0.008 (2)
F10	0.079 (2)	0.107 (2)	0.183 (4)	−0.0089 (18)	−0.057 (2)	0.043 (2)
F11	0.205 (5)	0.106 (3)	0.200 (5)	−0.040 (3)	−0.005 (4)	−0.057 (3)
F12	0.121 (3)	0.125 (3)	0.174 (4)	0.019 (2)	0.000 (3)	0.077 (3)
F13	0.087 (2)	0.084 (2)	0.228 (4)	−0.0305 (18)	−0.048 (2)	0.025 (2)
F14	0.267 (5)	0.116 (3)	0.073 (2)	−0.045 (3)	−0.013 (3)	0.008 (2)
F15	0.120 (5)	0.127 (5)	0.190 (6)	−0.005 (4)	−0.023 (4)	−0.001 (4)
F16	0.120 (5)	0.127 (5)	0.190 (6)	−0.005 (4)	−0.023 (4)	−0.001 (4)
C1	0.054 (2)	0.057 (2)	0.062 (2)	−0.0081 (19)	−0.005 (2)	−0.0031 (19)
C2	0.053 (2)	0.065 (3)	0.063 (3)	−0.004 (2)	−0.008 (2)	−0.006 (2)
C3	0.069 (3)	0.078 (3)	0.078 (3)	−0.001 (2)	−0.020 (3)	0.002 (3)
C4	0.070 (3)	0.063 (3)	0.084 (3)	−0.009 (2)	−0.004 (3)	0.007 (2)
C5	0.064 (3)	0.071 (3)	0.067 (3)	−0.016 (2)	−0.011 (2)	0.005 (2)
C6	0.070 (3)	0.056 (2)	0.064 (3)	−0.013 (2)	−0.004 (2)	−0.007 (2)
C7	0.063 (3)	0.055 (2)	0.057 (2)	−0.0109 (19)	−0.010 (2)	−0.0065 (19)
C8	0.066 (3)	0.059 (2)	0.062 (3)	−0.012 (2)	−0.011 (2)	−0.002 (2)
C9	0.075 (3)	0.053 (2)	0.058 (2)	−0.006 (2)	−0.013 (2)	−0.0058 (19)
C10	0.083 (3)	0.059 (3)	0.063 (3)	0.000 (2)	−0.019 (2)	−0.012 (2)
C11	0.104 (4)	0.072 (3)	0.075 (3)	0.004 (3)	−0.035 (3)	−0.008 (3)
C12	0.119 (5)	0.078 (4)	0.085 (4)	0.007 (3)	−0.043 (4)	−0.007 (3)
C13	0.115 (5)	0.102 (5)	0.104 (5)	0.030 (4)	−0.054 (4)	−0.022 (4)
C14	0.079 (4)	0.118 (5)	0.115 (5)	0.011 (3)	−0.026 (3)	−0.008 (4)
C15	0.076 (3)	0.094 (4)	0.092 (4)	0.004 (3)	−0.027 (3)	−0.002 (3)
C16	0.074 (3)	0.085 (3)	0.085 (3)	−0.019 (3)	0.003 (3)	−0.006 (3)
C17	0.051 (2)	0.075 (3)	0.082 (3)	−0.003 (2)	−0.010 (2)	−0.018 (2)
C18	0.055 (2)	0.068 (3)	0.069 (3)	−0.004 (2)	−0.013 (2)	−0.011 (2)
C19	0.054 (2)	0.070 (3)	0.079 (3)	0.002 (2)	−0.015 (2)	−0.018 (2)
C20	0.054 (3)	0.073 (3)	0.078 (3)	−0.002 (2)	−0.011 (2)	−0.019 (2)
C21	0.056 (3)	0.086 (3)	0.077 (3)	−0.012 (2)	−0.008 (2)	−0.028 (3)
C22	0.071 (3)	0.085 (4)	0.143 (5)	0.001 (3)	−0.033 (3)	−0.030 (4)
C23	0.072 (4)	0.116 (5)	0.181 (7)	−0.026 (4)	−0.024 (4)	−0.050 (5)
C24	0.060 (3)	0.158 (6)	0.125 (5)	−0.012 (4)	−0.014 (3)	−0.057 (5)
C25	0.062 (3)	0.132 (5)	0.110 (5)	0.005 (3)	−0.019 (3)	−0.030 (4)
C26	0.052 (3)	0.121 (4)	0.092 (4)	0.004 (3)	−0.019 (3)	−0.019 (3)
C27	0.055 (3)	0.095 (4)	0.136 (5)	0.007 (3)	−0.012 (3)	−0.040 (3)
C28	0.057 (2)	0.065 (3)	0.064 (3)	−0.011 (2)	−0.014 (2)	−0.006 (2)
C29	0.060 (3)	0.059 (2)	0.061 (2)	−0.002 (2)	−0.013 (2)	−0.005 (2)
C30	0.067 (3)	0.067 (3)	0.083 (3)	0.008 (2)	−0.007 (3)	−0.001 (3)
C31	0.092 (4)	0.067 (3)	0.127 (5)	−0.002 (3)	−0.016 (4)	0.008 (3)
C32	0.074 (3)	0.076 (3)	0.076 (3)	−0.023 (3)	−0.014 (2)	−0.003 (2)
C33	0.054 (2)	0.079 (3)	0.080 (3)	−0.011 (2)	−0.008 (2)	−0.025 (2)
C34	0.053 (2)	0.065 (3)	0.070 (3)	−0.008 (2)	−0.008 (2)	−0.013 (2)
C35	0.056 (3)	0.071 (3)	0.082 (3)	−0.013 (2)	−0.011 (2)	−0.016 (2)
C36	0.055 (3)	0.071 (3)	0.081 (3)	−0.008 (2)	−0.008 (2)	−0.017 (2)
C37	0.050 (2)	0.091 (3)	0.078 (3)	−0.002 (2)	−0.009 (2)	−0.021 (3)
C38	0.064 (3)	0.098 (4)	0.099 (4)	0.002 (3)	−0.012 (3)	−0.023 (3)
C39	0.065 (4)	0.128 (5)	0.126 (5)	0.009 (4)	−0.023 (3)	−0.023 (4)
C40	0.051 (3)	0.191 (8)	0.117 (5)	0.001 (4)	−0.018 (3)	−0.041 (5)
C41	0.071 (4)	0.142 (6)	0.130 (5)	−0.029 (4)	−0.007 (4)	−0.019 (5)
C42	0.057 (3)	0.136 (5)	0.103 (4)	−0.032 (3)	−0.001 (3)	−0.018 (4)
C43	0.064 (3)	0.094 (4)	0.119 (4)	−0.020 (3)	−0.008 (3)	−0.045 (3)
C44	0.080 (3)	0.066 (3)	0.063 (3)	0.003 (2)	−0.014 (2)	−0.010 (2)
C45	0.064 (3)	0.054 (2)	0.059 (2)	0.003 (2)	−0.007 (2)	−0.0060 (19)
C46	0.065 (3)	0.062 (3)	0.063 (3)	0.003 (2)	−0.004 (2)	−0.002 (2)
C47	0.083 (3)	0.061 (3)	0.057 (3)	−0.003 (2)	−0.001 (2)	−0.006 (2)
C48	0.098 (4)	0.059 (3)	0.069 (3)	−0.014 (3)	0.022 (3)	−0.011 (2)
C49	0.117 (5)	0.082 (4)	0.084 (4)	−0.019 (3)	0.016 (3)	−0.009 (3)
C50	0.151 (6)	0.091 (4)	0.089 (4)	−0.046 (5)	0.041 (4)	−0.019 (3)
C51	0.124 (6)	0.101 (5)	0.128 (6)	−0.047 (4)	0.051 (5)	−0.040 (4)
C52	0.095 (4)	0.094 (4)	0.130 (5)	−0.021 (3)	0.018 (4)	−0.023 (4)
C53	0.077 (3)	0.079 (3)	0.100 (4)	−0.014 (3)	0.009 (3)	−0.006 (3)
C54	0.091 (4)	0.096 (4)	0.085 (4)	0.006 (3)	−0.032 (3)	−0.012 (3)

Geometric parameters (Å, º)

S1—C6	1.711 (4)	C22—C23	1.377 (7)
S1—C9	1.724 (4)	C22—H22A	0.9601
S2—C17	1.718 (4)	C23—C24	1.365 (9)
S2—C20	1.727 (4)	C23—H23A	0.930
S3—C33	1.715 (5)	C24—C25	1.328 (8)
S3—C36	1.729 (4)	C24—H24A	0.930
S4—C44	1.717 (5)	C25—C26	1.402 (7)
S4—C47	1.720 (5)	C25—H25A	0.930
F1—C3	1.367 (6)	C26—H26A	0.930
F2—C3	1.335 (5)	C27—H27A	0.960
F3—C4	1.359 (5)	C27—H27B	0.960
F4—C4	1.329 (5)	C27—H27C	0.960
F5—C5	1.337 (5)	C28—C29	1.345 (6)
F6—C5	1.353 (5)	C28—C34	1.474 (6)
F7—C11	1.336 (3)	C28—C32	1.492 (6)
F8—C22	1.338 (3)	C29—C45	1.459 (6)
F9—C30	1.327 (6)	C29—C30	1.494 (6)
F10—C30	1.350 (6)	C30—C31	1.486 (7)
F11—C31	1.349 (3)	C31—C32	1.512 (7)
F12—C31	1.326 (3)	C33—C34	1.364 (6)
F13—C32	1.324 (5)	C33—C43	1.502 (6)
F14—C32	1.332 (5)	C34—C35	1.430 (6)
F15—C38	1.328 (3)	C35—C36	1.346 (6)
F16—C49	1.333 (3)	C35—H35A	0.930
C1—C2	1.352 (5)	C36—C37	1.470 (6)
C1—C7	1.464 (5)	C37—C38	1.363 (7)
C1—C5	1.498 (6)	C37—C42	1.408 (7)
C2—C18	1.468 (6)	C38—C39	1.358 (7)
C2—C3	1.494 (6)	C38—H38A	0.960
C3—C4	1.529 (7)	C39—C40	1.351 (9)
C4—C5	1.526 (6)	C39—H39A	0.930
C6—C7	1.366 (5)	C40—C41	1.370 (9)
C6—C16	1.503 (6)	C40—H40A	0.930
C7—C8	1.422 (6)	C41—C42	1.395 (7)
C8—C9	1.358 (5)	C41—H41A	0.930
C8—H8A	0.930	C42—H42A	0.930
C9—C10	1.474 (6)	C43—H43A	0.960
C10—C15	1.389 (7)	C43—H43B	0.960
C10—C11	1.392 (6)	C43—H43C	0.960
C11—C12	1.376 (7)	C44—C45	1.373 (6)
C11—H11A	0.9599	C44—C54	1.502 (6)
C12—C13	1.359 (8)	C45—C46	1.414 (6)
C12—H12A	0.930	C46—C47	1.365 (6)
C13—C14	1.362 (8)	C46—H46A	0.930
C13—H13A	0.930	C47—C48	1.470 (6)
C14—C15	1.396 (7)	C48—C49	1.382 (7)
C14—H14A	0.930	C48—C53	1.391 (7)
C15—H15A	0.930	C49—C50	1.346 (8)
C16—H16A	0.960	C49—H49A	0.9601
C16—H16B	0.960	C50—C51	1.364 (9)
C16—H16C	0.960	C50—H50A	0.930
C17—C18	1.366 (6)	C51—C52	1.356 (9)
C17—C27	1.502 (6)	C51—H51A	0.930
C18—C19	1.419 (6)	C52—C53	1.395 (7)
C19—C20	1.352 (6)	C52—H52A	0.930
C19—H19A	0.930	C53—H53A	0.930
C20—C21	1.470 (6)	C54—H54A	0.960
C21—C22	1.366 (7)	C54—H54B	0.960
C21—C26	1.399 (7)	C54—H54C	0.960
C6—S1—C9	93.1 (2)	H27A—C27—H27C	109.5
C17—S2—C20	92.6 (2)	H27B—C27—H27C	109.5
C33—S3—C36	92.9 (2)	C29—C28—C34	130.0 (4)
C44—S4—C47	93.5 (2)	C29—C28—C32	111.0 (4)
C2—C1—C7	130.3 (4)	C34—C28—C32	118.9 (4)
C2—C1—C5	110.5 (4)	C28—C29—C45	131.2 (4)
C7—C1—C5	119.1 (4)	C28—C29—C30	109.9 (4)
C1—C2—C18	129.6 (4)	C45—C29—C30	118.9 (4)
C1—C2—C3	110.2 (4)	F9—C30—F10	104.2 (4)
C18—C2—C3	120.2 (4)	F9—C30—C31	110.5 (5)
F2—C3—F1	106.8 (4)	F10—C30—C31	111.2 (4)
F2—C3—C2	115.4 (4)	F9—C30—C29	113.7 (4)
F1—C3—C2	111.2 (4)	F10—C30—C29	112.3 (4)
F2—C3—C4	110.8 (4)	C31—C30—C29	105.1 (4)
F1—C3—C4	107.3 (4)	F12—C31—F11	101.6 (4)
C2—C3—C4	105.0 (4)	F12—C31—C30	116.4 (4)
F4—C4—F3	107.5 (4)	F11—C31—C30	108.2 (5)
F4—C4—C5	114.2 (4)	F12—C31—C32	115.0 (5)
F3—C4—C5	108.1 (4)	F11—C31—C32	109.7 (4)
F4—C4—C3	114.8 (4)	C30—C31—C32	105.7 (4)
F3—C4—C3	108.8 (4)	F13—C32—F14	105.9 (4)
C5—C4—C3	103.1 (4)	F13—C32—C28	115.0 (4)
F5—C5—F6	106.1 (4)	F14—C32—C28	112.6 (4)
F5—C5—C1	113.8 (4)	F13—C32—C31	109.0 (4)
F6—C5—C1	112.2 (4)	F14—C32—C31	109.9 (4)
F5—C5—C4	111.1 (4)	C28—C32—C31	104.3 (4)
F6—C5—C4	109.3 (4)	C34—C33—C43	129.5 (4)
C1—C5—C4	104.4 (4)	C34—C33—S3	110.9 (3)
C7—C6—C16	129.8 (4)	C43—C33—S3	119.6 (3)
C7—C6—S1	110.9 (3)	C33—C34—C35	112.1 (4)
C16—C6—S1	119.2 (3)	C33—C34—C28	124.5 (4)
C6—C7—C8	112.1 (4)	C35—C34—C28	123.5 (4)
C6—C7—C1	125.9 (4)	C36—C35—C34	114.2 (4)
C8—C7—C1	122.0 (4)	C36—C35—H35A	122.9
C9—C8—C7	114.3 (4)	C34—C35—H35A	122.9
C9—C8—H8A	122.8	C35—C36—C37	127.7 (4)
C7—C8—H8A	122.8	C35—C36—S3	109.9 (3)
C8—C9—C10	128.8 (4)	C37—C36—S3	122.4 (4)
C8—C9—S1	109.5 (3)	C38—C37—C42	116.8 (5)
C10—C9—S1	121.7 (3)	C38—C37—C36	123.8 (5)
C15—C10—C11	117.7 (5)	C42—C37—C36	119.4 (5)
C15—C10—C9	120.1 (4)	F15—C38—C39	114.6 (6)
C11—C10—C9	122.1 (5)	F15—C38—C37	119.9 (5)
F7—C11—C12	116.0 (11)	C39—C38—C37	125.5 (6)
F7—C11—C10	122.4 (11)	C39—C38—H38A	117.2
C12—C11—C10	121.1 (6)	C37—C38—H38A	117.3
C12—C11—H11A	120.2	C40—C39—C38	117.4 (6)
C10—C11—H11A	118.7	C40—C39—H39A	121.3
C13—C12—C11	120.8 (6)	C38—C39—H39A	121.3
C13—C12—H12A	119.6	C39—C40—C41	120.8 (6)
C11—C12—H12A	119.6	C39—C40—H40A	119.6
C12—C13—C14	119.5 (6)	C41—C40—H40A	119.6
C12—C13—H13A	120.3	C40—C41—C42	121.5 (6)
C14—C13—H13A	120.3	C40—C41—H41A	119.2
C13—C14—C15	121.0 (6)	C42—C41—H41A	119.2
C13—C14—H14A	119.5	C41—C42—C37	118.0 (6)
C15—C14—H14A	119.5	C41—C42—H42A	121.0
C10—C15—C14	119.9 (5)	C37—C42—H42A	121.0
C10—C15—H15A	120.0	C33—C43—H43A	109.5
C14—C15—H15A	120.0	C33—C43—H43B	109.5
C6—C16—H16A	109.5	H43A—C43—H43B	109.5
C6—C16—H16B	109.5	C33—C43—H43C	109.5
H16A—C16—H16B	109.5	H43A—C43—H43C	109.5
C6—C16—H16C	109.5	H43B—C43—H43C	109.5
H16A—C16—H16C	109.5	C45—C44—C54	130.7 (4)
H16B—C16—H16C	109.5	C45—C44—S4	110.5 (4)
C18—C17—C27	129.6 (4)	C54—C44—S4	118.8 (3)
C18—C17—S2	110.9 (3)	C44—C45—C46	112.1 (4)
C27—C17—S2	119.5 (4)	C44—C45—C29	124.7 (4)
C17—C18—C19	112.2 (4)	C46—C45—C29	123.2 (4)
C17—C18—C2	124.6 (4)	C47—C46—C45	114.8 (4)
C19—C18—C2	123.3 (4)	C47—C46—H46A	122.6
C20—C19—C18	114.3 (4)	C45—C46—H46A	122.6
C20—C19—H19A	122.9	C46—C47—C48	128.3 (4)
C18—C19—H19A	122.9	C46—C47—S4	109.2 (4)
C19—C20—C21	127.7 (4)	C48—C47—S4	122.5 (4)
C19—C20—S2	110.0 (3)	C49—C48—C53	115.5 (5)
C21—C20—S2	122.2 (3)	C49—C48—C47	123.5 (5)
C22—C21—C26	116.2 (4)	C53—C48—C47	121.0 (4)
C22—C21—C20	123.9 (5)	F16—C49—C50	117.5 (7)
C26—C21—C20	119.8 (5)	F16—C49—C48	117.5 (7)
F8—C22—C21	119.4 (5)	C50—C49—C48	124.7 (7)
F8—C22—C23	115.3 (6)	C50—C49—H49A	118.6
C21—C22—C23	124.8 (5)	C48—C49—H49A	116.7
C21—C22—H22A	117.3	C49—C50—C51	119.2 (6)
C23—C22—H22A	117.9	C49—C50—H50A	120.4
C24—C23—C22	117.1 (6)	C51—C50—H50A	120.4
C24—C23—H23A	121.5	C52—C51—C50	119.1 (7)
C22—C23—H23A	121.5	C52—C51—H51A	120.4
C25—C24—C23	121.1 (6)	C50—C51—H51A	120.4
C25—C24—H24A	119.4	C51—C52—C53	121.6 (7)
C23—C24—H24A	119.4	C51—C52—H52A	119.2
C24—C25—C26	121.8 (6)	C53—C52—H52A	119.2
C24—C25—H25A	119.1	C48—C53—C52	119.9 (6)
C26—C25—H25A	119.1	C48—C53—H53A	120.0
C21—C26—C25	118.9 (6)	C52—C53—H53A	120.0
C21—C26—H26A	120.5	C44—C54—H54A	109.5
C25—C26—H26A	120.5	C44—C54—H54B	109.5
C17—C27—H27A	109.5	H54A—C54—H54B	109.5
C17—C27—H27B	109.5	C44—C54—H54C	109.5
H27A—C27—H27B	109.5	H54A—C54—H54C	109.5
C17—C27—H27C	109.5	H54B—C54—H54C	109.5