3-(4-{3,3,4,4,5,5-Hexafluoro-2-[5-(3-methoxy-phen-yl)-2-methyl-3-thien-yl]cyclo-pent-1-en-yl}-5-methyl-2-thien-yl)benzonitrile.

The title compound, C(29)H(19)F(6)NOS(2), is a new unsymmetrical photochromic diarylethene derivative with different meta-phenyl substituents. The distance between the two reactive (i.e. can be irradiated to form a new chemical bond) C atoms is 3.501 (4) Å; the dihedral angles between the mean plane of the main central cyclo-pentene ring and the thio-phene rings are 47.7 (5) and 45.1 (2)°, and those between the thio-phene rings and the adjacent benzene rings are 29.4 (2) and 28.4 (3)°. The three C atoms and the F atoms of hexa-fuorocyclo-pentene ring are disordered over two positions, with site-occupancy factors of 0.751 (4) and 0.249 (4).

Related literature

For related compounds, see: Irie (2000 ▶); Irie et al. (2001 ▶); Pu et al. (2007 ▶, 2008 ▶). For the synthesis of the precursors, see: Pu et al. (2006 ▶); Yang et al. (2007 ▶). For ring-closure reactions, see: Ramamurthy & Venkatesan (1987 ▶).

Experimental

Crystal data

C29H19F6NOS2

M = 575.57

Triclinic,

a = 8.6134 (11) Å

b = 11.5938 (15) Å

c = 14.5281 (19) Å

α = 68.346 (2)°

β = 88.783 (2)°

γ = 82.158 (2)°

V = 1335.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.974

10275 measured reflections

4948 independent reflections

3155 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.127

S = 1.03

4948 reflections

383 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034771/is2442sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034771/is2442Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H19F6NOS2	Z = 2
Mr = 575.57	F(000) = 588
Triclinic, P1	Dx = 1.432 Mg m−3
a = 8.6134 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5938 (15) Å	Cell parameters from 1963 reflections
c = 14.5281 (19) Å	θ = 2.4–21.8°
α = 68.346 (2)°	µ = 0.27 mm−1
β = 88.783 (2)°	T = 296 K
γ = 82.158 (2)°	Block, colourless
V = 1335.1 (3) Å3	0.15 × 0.13 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	4948 independent reflections
Radiation source: fine-focus sealed tube	3155 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.961, Tmax = 0.974	k = −14→14
10275 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.1414P] where P = (Fo2 + 2Fc2)/3
4948 reflections	(Δ/σ)max < 0.001
383 parameters	Δρmax = 0.30 e Å−3
16 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C2	0.8607 (7)	0.8219 (8)	0.1970 (5)	0.0616 (8)	0.751 (4)
C3	0.9550 (6)	0.8673 (5)	0.2620 (5)	0.0653 (13)	0.751 (4)
C4	0.8293 (11)	0.9522 (4)	0.2991 (4)	0.0510 (14)	0.751 (4)
F1	0.9173 (6)	0.7019 (6)	0.2107 (4)	0.0911 (14)	0.751 (4)
F2	0.8822 (6)	0.8920 (4)	0.1004 (4)	0.0963 (15)	0.751 (4)
F3	1.0171 (4)	0.7695 (3)	0.3431 (2)	0.1018 (11)	0.751 (4)
F4	1.0726 (3)	0.9286 (4)	0.2184 (3)	0.0965 (11)	0.751 (4)
F5	0.8628 (3)	0.9419 (3)	0.3914 (2)	0.0814 (9)	0.751 (4)
F6	0.8338 (4)	1.0749 (3)	0.2401 (2)	0.0802 (11)	0.751 (4)
C2'	0.8610 (15)	0.822 (2)	0.1990 (15)	0.0616 (8)	0.249 (4)
C3'	0.9453 (17)	0.9039 (17)	0.2351 (15)	0.0653 (13)	0.249 (4)
C4'	0.848 (4)	0.9271 (15)	0.2995 (13)	0.0510 (14)	0.249 (4)
F1'	0.904 (2)	0.700 (2)	0.2492 (14)	0.0911 (14)	0.249 (4)
F2'	0.877 (2)	0.8315 (16)	0.1047 (14)	0.0963 (15)	0.249 (4)
F3'	1.0853 (14)	0.8369 (11)	0.2718 (9)	0.1018 (11)	0.249 (4)
F4'	0.9731 (9)	0.9989 (10)	0.1527 (8)	0.0965 (11)	0.249 (4)
F5'	0.8899 (11)	0.8652 (10)	0.3949 (8)	0.0814 (9)	0.249 (4)
F6'	0.8456 (16)	1.0469 (13)	0.2921 (9)	0.0802 (11)	0.249 (4)
C1	0.6932 (3)	0.8443 (2)	0.2242 (2)	0.0474 (7)
C5	0.6795 (3)	0.9091 (2)	0.28436 (19)	0.0460 (7)
C6	0.4380 (3)	0.8805 (2)	0.13185 (19)	0.0451 (6)
C7	0.5704 (3)	0.8033 (2)	0.1798 (2)	0.0461 (7)
C8	0.5748 (3)	0.6789 (3)	0.1826 (2)	0.0516 (7)
H8	0.6580	0.6159	0.2111	0.062*
C9	0.4467 (3)	0.6608 (2)	0.1399 (2)	0.0482 (7)
C10	0.3912 (3)	1.0166 (2)	0.1107 (2)	0.0545 (7)
H10A	0.3333	1.0270	0.1650	0.082*
H10B	0.3269	1.0533	0.0511	0.082*
H10C	0.4834	1.0571	0.1024	0.082*
C11	0.4066 (4)	0.5459 (3)	0.1315 (2)	0.0520 (7)
C12	0.2517 (4)	0.5282 (3)	0.1271 (2)	0.0593 (8)
H12	0.1722	0.5894	0.1304	0.071*
C13	0.2130 (4)	0.4207 (3)	0.1178 (2)	0.0673 (9)
C14	0.3297 (5)	0.3315 (3)	0.1111 (2)	0.0739 (10)
H14	0.3046	0.2602	0.1029	0.089*
C15	0.4834 (5)	0.3476 (3)	0.1163 (2)	0.0688 (9)
H15	0.5620	0.2861	0.1126	0.083*
C16	0.5244 (4)	0.4538 (3)	0.1270 (2)	0.0620 (8)
H16	0.6293	0.4631	0.1310	0.074*
C17	0.0082 (6)	0.3090 (4)	0.1022 (4)	0.1315 (19)
H17A	0.0523	0.3022	0.0429	0.197*
H17B	−0.1042	0.3193	0.0965	0.197*
H17C	0.0442	0.2343	0.1580	0.197*
C18	0.4268 (3)	0.8736 (3)	0.37482 (19)	0.0480 (7)
C19	0.5397 (3)	0.9477 (2)	0.33159 (19)	0.0452 (7)
C20	0.5058 (3)	1.0699 (3)	0.33379 (19)	0.0480 (7)
H20	0.5720	1.1306	0.3087	0.058*
C21	0.3672 (3)	1.0900 (3)	0.3761 (2)	0.0503 (7)
C22	0.4206 (4)	0.7390 (3)	0.3910 (2)	0.0602 (8)
H22A	0.3639	0.7343	0.3366	0.090*
H22B	0.3687	0.7003	0.4515	0.090*
H22C	0.5253	0.6962	0.3951	0.090*
C23	0.2932 (3)	1.2076 (3)	0.38317 (19)	0.0511 (7)
C24	0.1306 (4)	1.2368 (3)	0.3827 (2)	0.0610 (8)
H24	0.0666	1.1797	0.3799	0.073*
C25	0.0641 (4)	1.3508 (3)	0.3865 (2)	0.0698 (9)
C26	0.1566 (5)	1.4367 (3)	0.3904 (2)	0.0796 (10)
H26	0.1110	1.5126	0.3935	0.095*
C27	0.3175 (5)	1.4096 (3)	0.3896 (3)	0.0760 (10)
H27	0.3805	1.4679	0.3912	0.091*
C28	0.3851 (4)	1.2964 (3)	0.3863 (2)	0.0619 (8)
H28	0.4937	1.2789	0.3863	0.074*
C29	−0.1043 (5)	1.3799 (4)	0.3840 (3)	0.0919 (13)
N1	−0.2356 (4)	1.4047 (4)	0.3815 (3)	0.1329 (16)
O1	0.0558 (3)	0.4145 (2)	0.1161 (2)	0.0975 (9)
S1	0.32016 (9)	0.79945 (7)	0.09174 (5)	0.0523 (2)
S2	0.28003 (9)	0.95549 (7)	0.41707 (6)	0.0570 (2)

	U11	U22	U33	U12	U13	U23
C2	0.0492 (19)	0.066 (2)	0.075 (2)	0.0006 (16)	0.0011 (16)	−0.0354 (18)
C3	0.036 (2)	0.067 (4)	0.096 (5)	0.000 (2)	−0.005 (2)	−0.035 (3)
C4	0.048 (3)	0.050 (3)	0.063 (2)	−0.008 (3)	0.0055 (16)	−0.0309 (19)
F1	0.0546 (17)	0.0930 (16)	0.155 (5)	0.0099 (12)	0.006 (3)	−0.087 (3)
F2	0.0647 (14)	0.153 (5)	0.0747 (16)	−0.029 (3)	0.0199 (11)	−0.042 (3)
F3	0.092 (2)	0.095 (2)	0.114 (3)	0.0270 (18)	−0.0439 (19)	−0.045 (2)
F4	0.0457 (17)	0.140 (3)	0.145 (3)	−0.0392 (19)	0.0381 (17)	−0.093 (2)
F5	0.0607 (16)	0.130 (3)	0.0804 (16)	−0.0208 (19)	−0.0012 (12)	−0.067 (2)
F6	0.0650 (15)	0.057 (2)	0.115 (3)	−0.0247 (14)	0.024 (2)	−0.023 (2)
C2'	0.0492 (19)	0.066 (2)	0.075 (2)	0.0006 (16)	0.0011 (16)	−0.0354 (18)
C3'	0.036 (2)	0.067 (4)	0.096 (5)	0.000 (2)	−0.005 (2)	−0.035 (3)
C4'	0.048 (3)	0.050 (3)	0.063 (2)	−0.008 (3)	0.0055 (16)	−0.0309 (19)
F1'	0.0546 (17)	0.0930 (16)	0.155 (5)	0.0099 (12)	0.006 (3)	−0.087 (3)
F2'	0.0647 (14)	0.153 (5)	0.0747 (16)	−0.029 (3)	0.0199 (11)	−0.042 (3)
F3'	0.092 (2)	0.095 (2)	0.114 (3)	0.0270 (18)	−0.0439 (19)	−0.045 (2)
F4'	0.0457 (17)	0.140 (3)	0.145 (3)	−0.0392 (19)	0.0381 (17)	−0.093 (2)
F5'	0.0607 (16)	0.130 (3)	0.0804 (16)	−0.0208 (19)	−0.0012 (12)	−0.067 (2)
F6'	0.0650 (15)	0.057 (2)	0.115 (3)	−0.0247 (14)	0.024 (2)	−0.023 (2)
C1	0.0408 (16)	0.0449 (16)	0.0557 (17)	−0.0031 (13)	0.0014 (13)	−0.0187 (14)
C5	0.0428 (16)	0.0451 (15)	0.0501 (16)	−0.0076 (12)	0.0010 (13)	−0.0170 (13)
C6	0.0476 (16)	0.0459 (16)	0.0465 (16)	−0.0076 (13)	0.0049 (13)	−0.0224 (13)
C7	0.0415 (16)	0.0491 (16)	0.0538 (17)	−0.0065 (13)	0.0037 (13)	−0.0261 (14)
C8	0.0479 (17)	0.0475 (17)	0.0603 (18)	0.0008 (13)	−0.0026 (14)	−0.0231 (14)
C9	0.0516 (17)	0.0431 (15)	0.0531 (17)	−0.0030 (13)	0.0019 (13)	−0.0226 (13)
C10	0.0567 (18)	0.0443 (16)	0.0621 (19)	−0.0028 (14)	−0.0032 (14)	−0.0205 (14)
C11	0.066 (2)	0.0456 (16)	0.0459 (16)	−0.0046 (15)	−0.0030 (14)	−0.0198 (13)
C12	0.068 (2)	0.0485 (17)	0.0628 (19)	−0.0063 (15)	−0.0068 (16)	−0.0218 (15)
C13	0.087 (3)	0.0470 (18)	0.068 (2)	−0.0173 (18)	−0.0074 (18)	−0.0186 (16)
C14	0.115 (3)	0.0417 (18)	0.069 (2)	−0.018 (2)	−0.003 (2)	−0.0227 (16)
C15	0.094 (3)	0.0420 (18)	0.068 (2)	0.0048 (18)	0.0031 (19)	−0.0227 (16)
C16	0.075 (2)	0.0513 (18)	0.0618 (19)	−0.0045 (16)	0.0054 (16)	−0.0252 (15)
C17	0.135 (4)	0.084 (3)	0.179 (5)	−0.048 (3)	−0.038 (3)	−0.038 (3)
C18	0.0487 (17)	0.0518 (16)	0.0472 (16)	−0.0107 (13)	0.0008 (13)	−0.0212 (14)
C19	0.0427 (16)	0.0483 (16)	0.0472 (16)	−0.0083 (13)	0.0006 (13)	−0.0200 (13)
C20	0.0450 (17)	0.0511 (17)	0.0520 (16)	−0.0127 (13)	0.0014 (13)	−0.0218 (14)
C21	0.0439 (17)	0.0579 (18)	0.0505 (16)	−0.0038 (14)	−0.0013 (13)	−0.0228 (14)
C22	0.068 (2)	0.0564 (18)	0.0583 (18)	−0.0188 (16)	0.0079 (15)	−0.0204 (15)
C23	0.0500 (17)	0.0582 (18)	0.0454 (16)	0.0004 (14)	−0.0003 (13)	−0.0221 (14)
C24	0.056 (2)	0.067 (2)	0.0564 (18)	−0.0040 (16)	0.0048 (15)	−0.0202 (16)
C25	0.061 (2)	0.070 (2)	0.062 (2)	0.0079 (18)	0.0113 (16)	−0.0133 (18)
C26	0.090 (3)	0.062 (2)	0.078 (2)	0.018 (2)	0.005 (2)	−0.0260 (19)
C27	0.087 (3)	0.059 (2)	0.086 (2)	−0.0044 (19)	−0.002 (2)	−0.0330 (19)
C28	0.059 (2)	0.063 (2)	0.067 (2)	−0.0024 (16)	−0.0043 (16)	−0.0303 (17)
C29	0.067 (3)	0.087 (3)	0.091 (3)	0.017 (2)	0.022 (2)	−0.008 (2)
N1	0.078 (3)	0.123 (3)	0.143 (3)	0.021 (2)	0.034 (2)	0.001 (2)
O1	0.096 (2)	0.0707 (16)	0.129 (2)	−0.0306 (15)	−0.0231 (17)	−0.0324 (16)
S1	0.0505 (4)	0.0490 (4)	0.0619 (5)	−0.0042 (3)	−0.0044 (3)	−0.0264 (4)
S2	0.0502 (5)	0.0664 (5)	0.0616 (5)	−0.0165 (4)	0.0121 (4)	−0.0295 (4)

C2—F1	1.352 (5)	C12—C13	1.386 (4)
C2—F2	1.361 (6)	C12—H12	0.9300
C2—C1	1.502 (6)	C13—O1	1.367 (4)
C2—C3	1.530 (6)	C13—C14	1.370 (5)
C3—F4	1.331 (5)	C14—C15	1.370 (5)
C3—F3	1.354 (5)	C14—H14	0.9300
C3—C4	1.583 (11)	C15—C16	1.388 (4)
C4—F5	1.337 (5)	C15—H15	0.9300
C4—F6	1.369 (5)	C16—H16	0.9300
C4—C5	1.492 (8)	C17—O1	1.424 (4)
C2'—F2'	1.340 (10)	C17—H17A	0.9600
C2'—F1'	1.339 (10)	C17—H17B	0.9600
C2'—C1	1.494 (10)	C17—H17C	0.9600
C2'—C3'	1.505 (10)	C18—C19	1.372 (4)
C3'—F4'	1.338 (10)	C18—C22	1.499 (4)
C3'—F3'	1.345 (10)	C18—S2	1.716 (3)
C3'—C4'	1.32 (4)	C19—C20	1.420 (4)
C4'—F5'	1.334 (10)	C20—C21	1.362 (4)
C4'—F6'	1.350 (10)	C20—H20	0.9300
C4'—C5	1.53 (3)	C21—C23	1.462 (4)
C1—C5	1.342 (4)	C21—S2	1.722 (3)
C1—C7	1.467 (4)	C22—H22A	0.9600
C5—C19	1.471 (4)	C22—H22B	0.9600
C6—C7	1.371 (4)	C22—H22C	0.9600
C6—C10	1.490 (3)	C23—C28	1.395 (4)
C6—S1	1.715 (3)	C23—C24	1.395 (4)
C7—C8	1.423 (3)	C24—C25	1.387 (4)
C8—C9	1.355 (4)	C24—H24	0.9300
C8—H8	0.9300	C25—C26	1.375 (5)
C9—C11	1.468 (4)	C25—C29	1.441 (5)
C9—S1	1.727 (3)	C26—C27	1.379 (5)
C10—H10A	0.9600	C26—H26	0.9300
C10—H10B	0.9600	C27—C28	1.379 (4)
C10—H10C	0.9600	C27—H27	0.9300
C11—C12	1.384 (4)	C28—H28	0.9300
C11—C16	1.389 (4)	C29—N1	1.126 (4)
F1—C2—F2	106.8 (5)	C12—C11—C16	119.0 (3)
F1—C2—C1	115.7 (5)	C12—C11—C9	120.8 (3)
F2—C2—C1	111.1 (5)	C16—C11—C9	120.2 (3)
F1—C2—C3	109.8 (6)	C13—C12—C11	121.1 (3)
F2—C2—C3	108.3 (6)	C13—C12—H12	119.5
C1—C2—C3	105.0 (4)	C11—C12—H12	119.5
F4—C3—F3	106.9 (4)	O1—C13—C14	125.5 (3)
F4—C3—C4	111.4 (5)	O1—C13—C12	114.9 (3)
F3—C3—C4	107.3 (5)	C14—C13—C12	119.6 (3)
F4—C3—C2	115.7 (6)	C13—C14—C15	119.8 (3)
F3—C3—C2	110.6 (5)	C13—C14—H14	120.1
C4—C3—C2	104.7 (5)	C15—C14—H14	120.1
F5—C4—F6	106.4 (4)	C14—C15—C16	121.4 (3)
F5—C4—C5	116.0 (6)	C14—C15—H15	119.3
F6—C4—C5	111.9 (5)	C16—C15—H15	119.3
F5—C4—C3	111.8 (5)	C15—C16—C11	119.1 (3)
F6—C4—C3	108.4 (6)	C15—C16—H16	120.5
C5—C4—C3	102.3 (4)	C11—C16—H16	120.5
F2'—C2'—F1'	102.3 (18)	O1—C17—H17A	109.5
F2'—C2'—C1	112.5 (15)	O1—C17—H17B	109.5
F1'—C2'—C1	103.8 (14)	H17A—C17—H17B	109.5
F2'—C2'—C3'	118.5 (18)	O1—C17—H17C	109.5
F1'—C2'—C3'	113.2 (17)	H17A—C17—H17C	109.5
C1—C2'—C3'	105.8 (11)	H17B—C17—H17C	109.5
F4'—C3'—F3'	106.7 (13)	C19—C18—C22	129.6 (3)
F4'—C3'—C4'	118.9 (17)	C19—C18—S2	110.3 (2)
F3'—C3'—C4'	116.3 (19)	C22—C18—S2	120.0 (2)
F4'—C3'—C2'	104.6 (18)	C18—C19—C20	112.7 (2)
F3'—C3'—C2'	106.0 (16)	C18—C19—C5	125.0 (2)
C4'—C3'—C2'	102.8 (16)	C20—C19—C5	122.3 (2)
F5'—C4'—F6'	101.1 (13)	C21—C20—C19	113.8 (2)
F5'—C4'—C5	108 (2)	C21—C20—H20	123.1
F6'—C4'—C5	107 (2)	C19—C20—H20	123.1
F5'—C4'—C3'	116 (2)	C20—C21—C23	127.3 (3)
F6'—C4'—C3'	110 (2)	C20—C21—S2	110.0 (2)
C5—C4'—C3'	113.5 (15)	C23—C21—S2	122.7 (2)
C5—C1—C7	129.3 (2)	C18—C22—H22A	109.5
C5—C1—C2'	110.0 (9)	C18—C22—H22B	109.5
C7—C1—C2'	120.6 (9)	H22A—C22—H22B	109.5
C5—C1—C2	111.0 (4)	C18—C22—H22C	109.5
C7—C1—C2	119.5 (4)	H22A—C22—H22C	109.5
C1—C5—C19	129.6 (2)	H22B—C22—H22C	109.5
C1—C5—C4'	103.5 (10)	C28—C23—C24	118.2 (3)
C19—C5—C4'	126.8 (9)	C28—C23—C21	120.1 (3)
C1—C5—C4	112.9 (3)	C24—C23—C21	121.6 (3)
C19—C5—C4	117.5 (4)	C25—C24—C23	120.2 (3)
C7—C6—C10	129.4 (2)	C25—C24—H24	119.9
C7—C6—S1	110.49 (19)	C23—C24—H24	119.9
C10—C6—S1	120.1 (2)	C26—C25—C24	120.8 (3)
C6—C7—C8	112.6 (2)	C26—C25—C29	120.0 (3)
C6—C7—C1	123.7 (2)	C24—C25—C29	119.2 (4)
C8—C7—C1	123.7 (2)	C25—C26—C27	119.6 (3)
C9—C8—C7	113.7 (2)	C25—C26—H26	120.2
C9—C8—H8	123.1	C27—C26—H26	120.2
C7—C8—H8	123.1	C28—C27—C26	120.1 (3)
C8—C9—C11	129.6 (3)	C28—C27—H27	119.9
C8—C9—S1	110.2 (2)	C26—C27—H27	119.9
C11—C9—S1	120.3 (2)	C27—C28—C23	121.1 (3)
C6—C10—H10A	109.5	C27—C28—H28	119.5
C6—C10—H10B	109.5	C23—C28—H28	119.5
H10A—C10—H10B	109.5	N1—C29—C25	178.8 (5)
C6—C10—H10C	109.5	C13—O1—C17	117.6 (3)
H10A—C10—H10C	109.5	C6—S1—C9	92.97 (13)
H10B—C10—H10C	109.5	C18—S2—C21	93.21 (13)
F1—C2—C3—F4	94.8 (6)	C3—C4—C5—C1	−16.5 (4)
F2—C2—C3—F4	−21.6 (6)	F5—C4—C5—C19	44.6 (5)
C1—C2—C3—F4	−140.3 (5)	F6—C4—C5—C19	−77.6 (5)
F1—C2—C3—F3	−26.9 (6)	C3—C4—C5—C19	166.6 (3)
F2—C2—C3—F3	−143.2 (5)	F5—C4—C5—C4'	−100 (4)
C1—C2—C3—F3	98.0 (5)	F6—C4—C5—C4'	138 (5)
F1—C2—C3—C4	−142.2 (4)	C3—C4—C5—C4'	22 (4)
F2—C2—C3—C4	101.5 (5)	C10—C6—C7—C8	−178.1 (3)
C1—C2—C3—C4	−17.3 (6)	S1—C6—C7—C8	0.5 (3)
F4—C3—C4—F5	−89.5 (6)	C10—C6—C7—C1	2.5 (4)
F3—C3—C4—F5	27.2 (7)	S1—C6—C7—C1	−178.9 (2)
C2—C3—C4—F5	144.8 (6)	C5—C1—C7—C6	48.2 (4)
F4—C3—C4—F6	27.5 (7)	C2'—C1—C7—C6	−127.5 (10)
F3—C3—C4—F6	144.1 (5)	C2—C1—C7—C6	−127.0 (4)
C2—C3—C4—F6	−98.3 (6)	C5—C1—C7—C8	−131.2 (3)
F4—C3—C4—C5	145.8 (5)	C2'—C1—C7—C8	53.2 (11)
F3—C3—C4—C5	−97.5 (5)	C2—C1—C7—C8	53.6 (5)
C2—C3—C4—C5	20.0 (5)	C6—C7—C8—C9	−1.5 (3)
F2'—C2'—C3'—F4'	21.7 (19)	C1—C7—C8—C9	177.9 (3)
F1'—C2'—C3'—F4'	141.4 (14)	C7—C8—C9—C11	−177.7 (3)
C1—C2'—C3'—F4'	−105.6 (16)	C7—C8—C9—S1	1.9 (3)
F2'—C2'—C3'—F3'	−91 (2)	C8—C9—C11—C12	150.9 (3)
F1'—C2'—C3'—F3'	28.8 (18)	S1—C9—C11—C12	−28.6 (4)
C1—C2'—C3'—F3'	141.8 (14)	C8—C9—C11—C16	−29.7 (4)
F2'—C2'—C3'—C4'	146.6 (15)	S1—C9—C11—C16	150.8 (2)
F1'—C2'—C3'—C4'	−93.7 (14)	C16—C11—C12—C13	−0.3 (4)
C1—C2'—C3'—C4'	19.3 (17)	C9—C11—C12—C13	179.1 (3)
F4'—C3'—C4'—F5'	−140.1 (16)	C11—C12—C13—O1	178.9 (3)
F3'—C3'—C4'—F5'	−10 (3)	C11—C12—C13—C14	−1.2 (5)
C2'—C3'—C4'—F5'	105 (2)	O1—C13—C14—C15	−178.3 (3)
F4'—C3'—C4'—F6'	−26 (3)	C12—C13—C14—C15	1.8 (5)
F3'—C3'—C4'—F6'	104 (2)	C13—C14—C15—C16	−0.9 (5)
C2'—C3'—C4'—F6'	−141.1 (17)	C14—C15—C16—C11	−0.6 (5)
F4'—C3'—C4'—C5	94 (2)	C12—C11—C16—C15	1.1 (4)
F3'—C3'—C4'—C5	−136.5 (16)	C9—C11—C16—C15	−178.2 (3)
C2'—C3'—C4'—C5	−21.2 (16)	C22—C18—C19—C20	−177.6 (3)
F2'—C2'—C1—C5	−141.7 (14)	S2—C18—C19—C20	0.3 (3)
F1'—C2'—C1—C5	108.5 (15)	C22—C18—C19—C5	4.4 (5)
C3'—C2'—C1—C5	−10.9 (15)	S2—C18—C19—C5	−177.7 (2)
F2'—C2'—C1—C7	35 (2)	C1—C5—C19—C18	42.1 (4)
F1'—C2'—C1—C7	−75.1 (15)	C4'—C5—C19—C18	−133.1 (7)
C3'—C2'—C1—C7	165.6 (8)	C4—C5—C19—C18	−141.5 (3)
F2'—C2'—C1—C2	15 (61)	C1—C5—C19—C20	−135.7 (3)
F1'—C2'—C1—C2	−95 (63)	C4'—C5—C19—C20	49.1 (8)
C3'—C2'—C1—C2	146 (63)	C4—C5—C19—C20	40.6 (4)
F1—C2—C1—C5	129.1 (6)	C18—C19—C20—C21	−1.4 (3)
F2—C2—C1—C5	−108.9 (5)	C5—C19—C20—C21	176.7 (2)
C3—C2—C1—C5	7.9 (6)	C19—C20—C21—C23	−175.1 (2)
F1—C2—C1—C7	−54.9 (7)	C19—C20—C21—S2	1.8 (3)
F2—C2—C1—C7	67.1 (7)	C20—C21—C23—C28	−28.5 (4)
C3—C2—C1—C7	−176.0 (3)	S2—C21—C23—C28	155.0 (2)
F1—C2—C1—C2'	105 (62)	C20—C21—C23—C24	148.8 (3)
F2—C2—C1—C2'	−133 (62)	S2—C21—C23—C24	−27.7 (4)
C3—C2—C1—C2'	−16 (62)	C28—C23—C24—C25	−0.7 (4)
C7—C1—C5—C19	6.8 (5)	C21—C23—C24—C25	−178.0 (3)
C2'—C1—C5—C19	−177.1 (9)	C23—C24—C25—C26	0.2 (5)
C2—C1—C5—C19	−177.6 (4)	C23—C24—C25—C29	178.8 (3)
C7—C1—C5—C4'	−177.1 (6)	C24—C25—C26—C27	0.6 (5)
C2'—C1—C5—C4'	−1.1 (11)	C29—C25—C26—C27	−178.0 (3)
C2—C1—C5—C4'	−1.6 (7)	C25—C26—C27—C28	−0.9 (5)
C7—C1—C5—C4	−169.6 (3)	C26—C27—C28—C23	0.4 (5)
C2'—C1—C5—C4	6.4 (10)	C24—C23—C28—C27	0.4 (4)
C2—C1—C5—C4	5.9 (5)	C21—C23—C28—C27	177.8 (3)
F5'—C4'—C5—C1	−115.1 (14)	C14—C13—O1—C17	−2.6 (5)
F6'—C4'—C5—C1	136.6 (12)	C12—C13—O1—C17	177.3 (3)
C3'—C4'—C5—C1	15.1 (13)	C7—C6—S1—C9	0.5 (2)
F5'—C4'—C5—C19	61.1 (15)	C10—C6—S1—C9	179.3 (2)
F6'—C4'—C5—C19	−47.2 (15)	C8—C9—S1—C6	−1.4 (2)
C3'—C4'—C5—C19	−168.7 (9)	C11—C9—S1—C6	178.2 (2)
F5'—C4'—C5—C4	101 (5)	C19—C18—S2—C21	0.6 (2)
F6'—C4'—C5—C4	−7(3)	C22—C18—S2—C21	178.7 (2)
C3'—C4'—C5—C4	−129 (5)	C20—C21—S2—C18	−1.4 (2)
F5—C4—C5—C1	−138.4 (4)	C23—C21—S2—C18	175.7 (2)
F6—C4—C5—C1	99.4 (5)