2-(1,2-Dimethyl-1H-indol-3-yl)-1-{5-[3-(1,3-dioxolan-2-yl)phen-yl]-2-methyl-thio-phen-3-yl}-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene.

The title compound, C(29)H(23)F(6)NO(2)S, a member of a new family of photochromic diaryl-ethene compounds having an unsymmetrically substituted hexa-fluoro-cyclo-pentene unit, displays dihedral angles between the indole and thio-phene rings of 52.5 (4)°, and between the indole ring and the planar C-C=C-C unit of the cyclopentene ring of 53.8 (6)°. The distance between the potentially reactive C atoms from the two heteroaryl substituents of 3.817 (6) Å is proven to be short enough for photocyclization to occur.

Related literature

For literature on photochromic diaryl­ethene compounds, see: Pu et al. (2007 ▶, 2010 ▶); Yamamoto et al. (2003 ▶).

Experimental

Crystal data

C29H23F6NO2S

M = 563.54

Monoclinic,

a = 10.7364 (13) Å

b = 9.8983 (12) Å

c = 24.020 (3) Å

β = 93.151 (1)°

V = 2548.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.50 × 0.38 × 0.30 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.906, T max = 0.942

22213 measured reflections

5816 independent reflections

4512 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.126

S = 1.03

5816 reflections

355 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 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 datablock(s) global, I. DOI: 10.1107/S1600536811043509/ng5249sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043509/ng5249Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043509/ng5249Isup3.cml

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

C29H23F6NO2S	F(000) = 1160
Mr = 563.54	Dx = 1.469 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.7364 (13) Å	Cell parameters from 8530 reflections
b = 9.8983 (12) Å	θ = 2.5–28.0°
c = 24.020 (3) Å	µ = 0.20 mm−1
β = 93.151 (1)°	T = 296 K
V = 2548.8 (5) Å3	Block, yellow
Z = 4	0.50 × 0.38 × 0.30 mm

Bruker SMART APEX diffractometer	5816 independent reflections
Radiation source: fine-focus sealed tube	4512 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.906, Tmax = 0.942	k = −12→12
22213 measured reflections	l = −31→31

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.789P] where P = (Fo2 + 2Fc2)/3
5816 reflections	(Δ/σ)max = 0.011
355 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.46926 (4)	0.75926 (5)	0.44072 (2)	0.05075 (14)
C2	0.5797 (3)	1.4850 (2)	0.26912 (11)	0.0767 (7)
H2A	0.5468	1.5124	0.2324	0.092*
H2B	0.6701	1.4859	0.2696	0.092*
C1	0.5343 (2)	1.5767 (2)	0.31281 (11)	0.0697 (6)
H1A	0.5936	1.6486	0.3215	0.084*
H1B	0.4543	1.6162	0.3012	0.084*
C3	0.4832 (2)	1.3650 (2)	0.33581 (9)	0.0574 (5)
H3	0.3919	1.3642	0.3311	0.069*
O1	0.52349 (16)	1.48886 (14)	0.35886 (7)	0.0691 (4)
O2	0.53560 (19)	1.35553 (16)	0.28268 (7)	0.0788 (5)
C9	0.44801 (16)	1.14124 (17)	0.38049 (7)	0.0424 (4)
H9	0.3674	1.1422	0.3642	0.051*
C8	0.48836 (15)	1.03020 (17)	0.41218 (7)	0.0394 (4)
C7	0.60943 (17)	1.0324 (2)	0.43654 (8)	0.0477 (4)
H7	0.6381	0.9596	0.4581	0.057*
C6	0.68702 (18)	1.1412 (2)	0.42901 (8)	0.0550 (5)
H6	0.7676	1.1409	0.4454	0.066*
C4	0.52623 (17)	1.25041 (18)	0.37281 (8)	0.0453 (4)
C5	0.64630 (18)	1.2503 (2)	0.39749 (8)	0.0523 (5)
H5	0.6989	1.3235	0.3927	0.063*
C10	0.40687 (16)	0.91279 (16)	0.41941 (7)	0.0392 (4)
C13	0.32653 (16)	0.68064 (17)	0.43779 (7)	0.0438 (4)
C12	0.23425 (15)	0.76930 (16)	0.42070 (7)	0.0372 (3)
C11	0.28040 (15)	0.90194 (16)	0.41100 (7)	0.0390 (4)
H11	0.2293	0.9741	0.4000	0.047*
C14	0.3162 (2)	0.5367 (2)	0.45587 (10)	0.0615 (5)
H14A	0.2382	0.5235	0.4728	0.092*
H14B	0.3837	0.5157	0.4824	0.092*
H14C	0.3201	0.4785	0.4240	0.092*
C19	0.04988 (15)	0.62631 (16)	0.38624 (6)	0.0351 (3)
C15	0.10223 (15)	0.72872 (15)	0.41630 (6)	0.0357 (3)
C18	−0.08018 (16)	0.60133 (17)	0.40400 (7)	0.0412 (4)
C16	0.00880 (17)	0.79637 (17)	0.45098 (7)	0.0419 (4)
C17	−0.11661 (17)	0.73266 (19)	0.43227 (8)	0.0467 (4)
C27	0.09376 (15)	0.40600 (16)	0.33100 (7)	0.0388 (3)
C21	0.15871 (16)	0.60655 (17)	0.29688 (7)	0.0394 (4)
C20	0.10126 (15)	0.54940 (16)	0.34138 (6)	0.0367 (3)
C26	0.05000 (19)	0.29491 (18)	0.35967 (8)	0.0495 (4)
H26	0.0145	0.3059	0.3938	0.059*
C22	0.14977 (16)	0.38410 (17)	0.28003 (7)	0.0424 (4)
C23	0.1598 (2)	0.25562 (19)	0.25678 (9)	0.0539 (5)
H23	0.1963	0.2429	0.2230	0.065*
C25	0.0604 (2)	0.16781 (19)	0.33630 (10)	0.0590 (5)
H25	0.0308	0.0932	0.3551	0.071*
C24	0.1139 (2)	0.1490 (2)	0.28563 (10)	0.0604 (5)
H24	0.1186	0.0623	0.2710	0.072*
C28	0.17998 (19)	0.75138 (18)	0.28411 (8)	0.0500 (4)
H28A	0.2667	0.7725	0.2910	0.075*
H28B	0.1309	0.8066	0.3074	0.075*
H28C	0.1561	0.7686	0.2457	0.075*
C29	0.2481 (2)	0.5262 (2)	0.20780 (8)	0.0638 (6)
H29A	0.3058	0.4539	0.2025	0.096*
H29B	0.2919	0.6108	0.2086	0.096*
H29C	0.1855	0.5265	0.1777	0.096*
N1	0.18883 (14)	0.50697 (15)	0.26043 (6)	0.0442 (3)
F6	−0.08404 (11)	0.49895 (11)	0.44167 (5)	0.0586 (3)
F5	−0.16255 (10)	0.56709 (13)	0.36180 (5)	0.0624 (3)
F4	−0.19297 (12)	0.71618 (14)	0.47397 (6)	0.0710 (4)
F2	0.00594 (12)	0.93212 (11)	0.44437 (6)	0.0672 (3)
F1	0.03219 (11)	0.77538 (14)	0.50619 (4)	0.0639 (3)
F3	−0.17684 (12)	0.81256 (14)	0.39387 (6)	0.0727 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0373 (2)	0.0444 (3)	0.0708 (3)	0.00047 (18)	0.0052 (2)	0.0026 (2)
C2	0.0806 (16)	0.0674 (15)	0.0844 (16)	−0.0038 (12)	0.0267 (13)	0.0159 (12)
C1	0.0631 (14)	0.0481 (11)	0.0991 (18)	−0.0011 (10)	0.0144 (12)	0.0125 (11)
C3	0.0507 (11)	0.0501 (11)	0.0722 (13)	−0.0103 (9)	0.0109 (10)	0.0030 (9)
O1	0.0832 (11)	0.0417 (7)	0.0850 (11)	−0.0074 (7)	0.0272 (9)	−0.0044 (7)
O2	0.1211 (15)	0.0564 (9)	0.0603 (9)	−0.0133 (9)	0.0182 (9)	0.0006 (7)
C9	0.0356 (8)	0.0440 (9)	0.0476 (9)	−0.0075 (7)	0.0042 (7)	−0.0071 (7)
C8	0.0384 (8)	0.0429 (9)	0.0374 (8)	−0.0070 (7)	0.0063 (6)	−0.0094 (7)
C7	0.0415 (9)	0.0552 (11)	0.0461 (9)	−0.0045 (8)	0.0002 (7)	−0.0056 (8)
C6	0.0385 (9)	0.0708 (13)	0.0552 (11)	−0.0129 (9)	−0.0019 (8)	−0.0087 (10)
C4	0.0434 (9)	0.0431 (9)	0.0502 (10)	−0.0082 (7)	0.0109 (7)	−0.0078 (7)
C5	0.0448 (10)	0.0540 (11)	0.0589 (11)	−0.0199 (8)	0.0092 (8)	−0.0110 (9)
C10	0.0411 (9)	0.0377 (8)	0.0391 (8)	−0.0045 (7)	0.0053 (7)	−0.0053 (6)
C13	0.0425 (9)	0.0388 (9)	0.0508 (10)	−0.0024 (7)	0.0091 (7)	−0.0007 (7)
C12	0.0391 (8)	0.0367 (8)	0.0361 (8)	−0.0040 (6)	0.0060 (6)	−0.0034 (6)
C11	0.0392 (8)	0.0352 (8)	0.0425 (8)	−0.0029 (6)	0.0013 (7)	−0.0012 (6)
C14	0.0535 (12)	0.0451 (11)	0.0870 (15)	0.0018 (9)	0.0132 (11)	0.0143 (10)
C19	0.0383 (8)	0.0342 (8)	0.0330 (7)	−0.0025 (6)	0.0045 (6)	0.0039 (6)
C15	0.0383 (8)	0.0343 (8)	0.0349 (7)	−0.0024 (6)	0.0059 (6)	0.0021 (6)
C18	0.0384 (9)	0.0442 (9)	0.0409 (8)	−0.0072 (7)	0.0021 (7)	0.0051 (7)
C16	0.0494 (10)	0.0380 (8)	0.0391 (8)	−0.0008 (7)	0.0109 (7)	−0.0005 (7)
C17	0.0409 (9)	0.0526 (10)	0.0476 (9)	0.0046 (8)	0.0105 (7)	0.0065 (8)
C27	0.0403 (9)	0.0367 (8)	0.0393 (8)	−0.0028 (7)	−0.0003 (7)	−0.0005 (6)
C21	0.0408 (9)	0.0404 (9)	0.0373 (8)	−0.0059 (7)	0.0040 (7)	−0.0007 (6)
C20	0.0395 (8)	0.0350 (8)	0.0358 (8)	−0.0060 (6)	0.0030 (6)	0.0002 (6)
C26	0.0570 (11)	0.0399 (9)	0.0515 (10)	−0.0055 (8)	0.0033 (8)	0.0063 (8)
C22	0.0433 (9)	0.0405 (9)	0.0431 (9)	−0.0005 (7)	0.0004 (7)	−0.0043 (7)
C23	0.0571 (11)	0.0481 (10)	0.0564 (11)	0.0054 (9)	0.0019 (9)	−0.0123 (8)
C25	0.0664 (13)	0.0358 (9)	0.0739 (13)	−0.0056 (9)	−0.0037 (11)	0.0095 (9)
C24	0.0649 (13)	0.0373 (10)	0.0779 (14)	0.0043 (9)	−0.0067 (11)	−0.0090 (9)
C28	0.0606 (11)	0.0437 (10)	0.0465 (10)	−0.0117 (8)	0.0104 (8)	0.0052 (7)
C29	0.0730 (14)	0.0741 (14)	0.0465 (10)	−0.0085 (11)	0.0246 (10)	−0.0059 (10)
N1	0.0489 (8)	0.0463 (8)	0.0385 (7)	−0.0040 (6)	0.0108 (6)	−0.0025 (6)
F6	0.0633 (7)	0.0500 (6)	0.0646 (7)	−0.0054 (5)	0.0230 (6)	0.0172 (5)
F5	0.0442 (6)	0.0782 (8)	0.0638 (7)	−0.0133 (5)	−0.0051 (5)	−0.0084 (6)
F4	0.0568 (7)	0.0845 (9)	0.0753 (8)	−0.0072 (6)	0.0349 (6)	−0.0066 (7)
F2	0.0781 (8)	0.0367 (6)	0.0900 (9)	0.0017 (5)	0.0336 (7)	−0.0054 (6)
F1	0.0649 (8)	0.0909 (9)	0.0365 (5)	−0.0039 (6)	0.0086 (5)	−0.0064 (5)
F3	0.0695 (8)	0.0693 (8)	0.0777 (8)	0.0233 (7)	−0.0101 (7)	0.0093 (7)

S1—C13	1.7167 (18)	C19—C20	1.453 (2)
S1—C10	1.7269 (18)	C19—C18	1.503 (2)
C2—O2	1.411 (3)	C15—C16	1.497 (2)
C2—C1	1.490 (4)	C18—F5	1.351 (2)
C2—H2A	0.9700	C18—F6	1.3608 (19)
C2—H2B	0.9700	C18—C17	1.527 (3)
C1—O1	1.417 (3)	C16—F1	1.352 (2)
C1—H1A	0.9700	C16—F2	1.353 (2)
C1—H1B	0.9700	C16—C17	1.532 (3)
C3—O1	1.404 (2)	C17—F4	1.339 (2)
C3—O2	1.426 (3)	C17—F3	1.352 (2)
C3—C4	1.498 (3)	C27—C26	1.393 (2)
C3—H3	0.9800	C27—C22	1.410 (2)
C9—C4	1.387 (2)	C27—C20	1.443 (2)
C9—C8	1.392 (2)	C21—N1	1.369 (2)
C9—H9	0.9300	C21—C20	1.384 (2)
C8—C7	1.396 (2)	C21—C28	1.486 (2)
C8—C10	1.471 (2)	C26—C25	1.385 (3)
C7—C6	1.380 (3)	C26—H26	0.9300
C7—H7	0.9300	C22—N1	1.378 (2)
C6—C5	1.376 (3)	C22—C23	1.395 (2)
C6—H6	0.9300	C23—C24	1.369 (3)
C4—C5	1.389 (3)	C23—H23	0.9300
C5—H5	0.9300	C25—C24	1.387 (3)
C10—C11	1.366 (2)	C25—H25	0.9300
C13—C12	1.369 (2)	C24—H24	0.9300
C13—C14	1.496 (2)	C28—H28A	0.9600
C12—C11	1.427 (2)	C28—H28B	0.9600
C12—C15	1.471 (2)	C28—H28C	0.9600
C11—H11	0.9300	C29—N1	1.458 (2)
C14—H14A	0.9600	C29—H29A	0.9600
C14—H14B	0.9600	C29—H29B	0.9600
C14—H14C	0.9600	C29—H29C	0.9600
C19—C15	1.349 (2)
C13—S1—C10	93.21 (8)	C19—C15—C12	127.95 (15)
O2—C2—C1	105.30 (19)	C19—C15—C16	111.21 (14)
O2—C2—H2A	110.7	C12—C15—C16	120.68 (14)
C1—C2—H2A	110.7	F5—C18—F6	105.62 (13)
O2—C2—H2B	110.7	F5—C18—C19	114.11 (14)
C1—C2—H2B	110.7	F6—C18—C19	111.96 (14)
H2A—C2—H2B	108.8	F5—C18—C17	111.96 (15)
O1—C1—C2	102.70 (18)	F6—C18—C17	108.68 (14)
O1—C1—H1A	111.2	C19—C18—C17	104.53 (13)
C2—C1—H1A	111.2	F1—C16—F2	105.63 (14)
O1—C1—H1B	111.2	F1—C16—C15	112.52 (15)
C2—C1—H1B	111.2	F2—C16—C15	112.99 (13)
H1A—C1—H1B	109.1	F1—C16—C17	109.72 (14)
O1—C3—O2	106.39 (15)	F2—C16—C17	111.13 (15)
O1—C3—C4	110.41 (17)	C15—C16—C17	104.93 (14)
O2—C3—C4	110.92 (17)	F4—C17—F3	106.98 (15)
O1—C3—H3	109.7	F4—C17—C18	114.29 (15)
O2—C3—H3	109.7	F3—C17—C18	108.60 (15)
C4—C3—H3	109.7	F4—C17—C16	113.28 (15)
C3—O1—C1	105.36 (17)	F3—C17—C16	109.82 (15)
C2—O2—C3	107.51 (17)	C18—C17—C16	103.79 (14)
C4—C9—C8	121.01 (17)	C26—C27—C22	118.65 (16)
C4—C9—H9	119.5	C26—C27—C20	135.12 (16)
C8—C9—H9	119.5	C22—C27—C20	106.19 (14)
C9—C8—C7	118.14 (16)	N1—C21—C20	109.31 (14)
C9—C8—C10	121.28 (15)	N1—C21—C28	121.21 (15)
C7—C8—C10	120.58 (16)	C20—C21—C28	129.32 (16)
C6—C7—C8	120.79 (19)	C21—C20—C27	106.96 (14)
C6—C7—H7	119.6	C21—C20—C19	124.20 (15)
C8—C7—H7	119.6	C27—C20—C19	128.61 (14)
C7—C6—C5	120.59 (18)	C25—C26—C27	118.68 (18)
C7—C6—H6	119.7	C25—C26—H26	120.7
C5—C6—H6	119.7	C27—C26—H26	120.7
C9—C4—C5	119.80 (18)	N1—C22—C23	129.50 (17)
C9—C4—C3	119.96 (17)	N1—C22—C27	108.26 (14)
C5—C4—C3	120.18 (17)	C23—C22—C27	122.24 (17)
C6—C5—C4	119.67 (17)	C24—C23—C22	117.54 (19)
C6—C5—H5	120.2	C24—C23—H23	121.2
C4—C5—H5	120.2	C22—C23—H23	121.2
C11—C10—C8	129.61 (16)	C26—C25—C24	121.65 (19)
C11—C10—S1	109.93 (12)	C26—C25—H25	119.2
C8—C10—S1	120.45 (13)	C24—C25—H25	119.2
C12—C13—C14	129.32 (17)	C23—C24—C25	121.21 (18)
C12—C13—S1	110.56 (13)	C23—C24—H24	119.4
C14—C13—S1	120.02 (14)	C25—C24—H24	119.4
C13—C12—C11	112.74 (15)	C21—C28—H28A	109.5
C13—C12—C15	121.65 (15)	C21—C28—H28B	109.5
C11—C12—C15	125.54 (15)	H28A—C28—H28B	109.5
C10—C11—C12	113.54 (15)	C21—C28—H28C	109.5
C10—C11—H11	123.2	H28A—C28—H28C	109.5
C12—C11—H11	123.2	H28B—C28—H28C	109.5
C13—C14—H14A	109.5	N1—C29—H29A	109.5
C13—C14—H14B	109.5	N1—C29—H29B	109.5
H14A—C14—H14B	109.5	H29A—C29—H29B	109.5
C13—C14—H14C	109.5	N1—C29—H29C	109.5
H14A—C14—H14C	109.5	H29A—C29—H29C	109.5
H14B—C14—H14C	109.5	H29B—C29—H29C	109.5
C15—C19—C20	128.81 (15)	C21—N1—C22	109.27 (13)
C15—C19—C18	109.75 (14)	C21—N1—C29	126.17 (16)
C20—C19—C18	121.40 (14)	C22—N1—C29	124.52 (15)
O2—C2—C1—O1	26.9 (3)	C19—C15—C16—F2	−128.64 (16)
O2—C3—O1—C1	31.8 (2)	C12—C15—C16—F2	55.7 (2)
C4—C3—O1—C1	152.24 (17)	C19—C15—C16—C17	−7.41 (18)
C2—C1—O1—C3	−35.9 (2)	C12—C15—C16—C17	176.91 (14)
C1—C2—O2—C3	−8.2 (3)	F5—C18—C17—F4	88.26 (18)
O1—C3—O2—C2	−14.1 (3)	F6—C18—C17—F4	−28.0 (2)
C4—C3—O2—C2	−134.2 (2)	C19—C18—C17—F4	−147.72 (15)
C4—C9—C8—C7	0.7 (2)	F5—C18—C17—F3	−31.07 (19)
C4—C9—C8—C10	−178.57 (15)	F6—C18—C17—F3	−147.36 (14)
C9—C8—C7—C6	−0.5 (3)	C19—C18—C17—F3	92.94 (16)
C10—C8—C7—C6	178.79 (16)	F5—C18—C17—C16	−147.87 (14)
C8—C7—C6—C5	0.3 (3)	F6—C18—C17—C16	95.84 (15)
C8—C9—C4—C5	−0.7 (3)	C19—C18—C17—C16	−23.86 (16)
C8—C9—C4—C3	176.42 (16)	F1—C16—C17—F4	22.7 (2)
O1—C3—C4—C9	140.83 (17)	F2—C16—C17—F4	−93.70 (18)
O2—C3—C4—C9	−101.5 (2)	C15—C16—C17—F4	143.86 (15)
O1—C3—C4—C5	−42.0 (2)	F1—C16—C17—F3	142.28 (15)
O2—C3—C4—C5	75.6 (2)	F2—C16—C17—F3	25.83 (19)
C7—C6—C5—C4	−0.3 (3)	C15—C16—C17—F3	−96.61 (16)
C9—C4—C5—C6	0.5 (3)	F1—C16—C17—C18	−101.77 (15)
C3—C4—C5—C6	−176.59 (18)	F2—C16—C17—C18	141.78 (14)
C9—C8—C10—C11	−17.9 (3)	C15—C16—C17—C18	19.34 (17)
C7—C8—C10—C11	162.90 (17)	N1—C21—C20—C27	−1.06 (19)
C9—C8—C10—S1	161.20 (13)	C28—C21—C20—C27	174.27 (18)
C7—C8—C10—S1	−18.0 (2)	N1—C21—C20—C19	−176.00 (15)
C13—S1—C10—C11	0.47 (13)	C28—C21—C20—C19	−0.7 (3)
C13—S1—C10—C8	−178.77 (14)	C26—C27—C20—C21	178.3 (2)
C10—S1—C13—C12	0.33 (14)	C22—C27—C20—C21	0.73 (19)
C10—S1—C13—C14	−176.36 (16)	C26—C27—C20—C19	−7.1 (3)
C14—C13—C12—C11	175.27 (19)	C22—C27—C20—C19	175.36 (16)
S1—C13—C12—C11	−1.02 (19)	C15—C19—C20—C21	−47.4 (3)
C14—C13—C12—C15	−1.8 (3)	C18—C19—C20—C21	130.03 (17)
S1—C13—C12—C15	−178.09 (12)	C15—C19—C20—C27	138.83 (19)
C8—C10—C11—C12	178.01 (15)	C18—C19—C20—C27	−43.8 (2)
S1—C10—C11—C12	−1.14 (18)	C22—C27—C26—C25	−1.6 (3)
C13—C12—C11—C10	1.4 (2)	C20—C27—C26—C25	−178.92 (19)
C15—C12—C11—C10	178.36 (15)	C26—C27—C22—N1	−178.17 (16)
C20—C19—C15—C12	−15.4 (3)	C20—C27—C22—N1	−0.14 (19)
C18—C19—C15—C12	166.98 (15)	C26—C27—C22—C23	1.7 (3)
C20—C19—C15—C16	169.35 (16)	C20—C27—C22—C23	179.72 (17)
C18—C19—C15—C16	−8.30 (19)	N1—C22—C23—C24	179.24 (19)
C13—C12—C15—C19	−56.5 (2)	C27—C22—C23—C24	−0.6 (3)
C11—C12—C15—C19	126.83 (19)	C27—C26—C25—C24	0.5 (3)
C13—C12—C15—C16	118.39 (18)	C22—C23—C24—C25	−0.6 (3)
C11—C12—C15—C16	−58.3 (2)	C26—C25—C24—C23	0.6 (3)
C15—C19—C18—F5	143.23 (15)	C20—C21—N1—C22	1.0 (2)
C20—C19—C18—F5	−34.6 (2)	C28—C21—N1—C22	−174.78 (17)
C15—C19—C18—F6	−96.87 (17)	C20—C21—N1—C29	178.59 (18)
C20—C19—C18—F6	85.28 (18)	C28—C21—N1—C29	2.8 (3)
C15—C19—C18—C17	20.60 (18)	C23—C22—N1—C21	179.63 (19)
C20—C19—C18—C17	−157.26 (15)	C27—C22—N1—C21	−0.52 (19)
C19—C15—C16—F1	111.83 (16)	C23—C22—N1—C29	2.0 (3)
C12—C15—C16—F1	−63.85 (19)	C27—C22—N1—C29	−178.16 (18)