1,2-Bis[5-(2,2'-dicyano-vinyl)-2-n-pentyl-3-thien-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene: a new photochromic diaryl-ethene compound.

The title compound, C(31)H(26)F(6)N(4)S(2), is a new photochromic dithienylethene with dicyano-vinyl subsitituents. In the crystal structure, the mol-ecule adopts a photoactive anti-parallel conformation, with two n-pentyl groups located on opposite sides of the cyclo-pentene ring. The cyclo-pentene ring assumes an envelope conformation. The distance between the two reactive C atoms on the thio-phene rings is 3.834 (7) Å. One of the n-pentyl groups is disordered over two positions; the site occupancy factors are ca 0.7 and 0.3.

Related literature

For general background, see: Gilat et al. (1993 ▶, 1995 ▶); Irie (2000 ▶); Pu et al. (2003 ▶, 2005 ▶); Tian & Yang (2004 ▶); Yamaguchi & Irie (2006 ▶); Zheng et al. (2007 ▶). For related structures, see: Kobatake et al. (2004 ▶); Woodward & Hoffmann (1970 ▶).

Experimental

Crystal data

C31H26F6N4S2

M = 632.68

Triclinic,

a = 9.2500 (12) Å

b = 12.3670 (16) Å

c = 15.596 (2) Å

α = 67.730 (2)°

β = 85.482 (2)°

γ = 72.804 (2)°

V = 1576.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 291 (2) K

0.29 × 0.21 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.932, T max = 0.963

12153 measured reflections

5828 independent reflections

3782 reflections with I > 2s˘I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.142

S = 1.03

5828 reflections

384 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800202X/xu2397sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800202X/xu2397Isup2.hkl

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

C31H26F6N4S2	Z = 2
Mr = 632.68	F000 = 652
Triclinic, P1	Dx = 1.333 Mg m−3
Hall symbol: -p 1	Melting point: 404.2 K
a = 9.2500 (12) Å	Mo Kα radiation λ = 0.71073 Å
b = 12.3670 (16) Å	Cell parameters from 2550 reflections
c = 15.596 (2) Å	θ = 2.5–21.8º
α = 67.730 (2)º	µ = 0.23 mm−1
β = 85.482 (2)º	T = 291 (2) K
γ = 72.804 (2)º	Block, colourless
V = 1576.1 (4) Å3	0.29 × 0.21 × 0.16 mm

Bruker SMART APEXII CCD area-detector diffractometer	5828 independent reflections
Radiation source: fine-focus sealed tube	3782 reflections with I > 2s˘I)
Monochromator: graphite	Rint = 0.026
T = 291(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.932, Tmax = 0.963	k = −14→14
12153 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.4466P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
5828 reflections	Δρmax = 0.41 e Å−3
384 parameters	Δρmin = −0.26 e Å−3
14 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The structure of (Ia) was confirmed by melting point, NMR, MS, IR, elemental analysis. (m.p.: 404.2 K). 1H NMR (400 MHz, CDCl3): δ 0.87 (t, 6H, J=7.0 Hz), δ 1.23 (m, 4H), δ 1.43 (m, 4H), δ 2.34 (t, 4H, J=7.8 Hz), δ 7.64 (s, 2H), δ 7.79 (s, 2H). 13C NMR (100 MHz,CDCl3): δ 113.82, 22.24, 29.91, 30.82, 31.34, 79.87, 112.47, 113.15, 125.31, 133.80, 137.42, 149.55, 159.50. MS m/z (M+) 631.0 (–H). IR (KBr, cm-1): 746, 929, 1139, 1276, 1436, 1575, 2225, 2931. Anal. Calcd for C31H26F6N4S2 (%): Calcd C, 58.85; H, 4.14; N, 8.86. Found C, 58.92; H, 3.72; N, 8.53.

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	Occ. (<1)
C27	0.0741 (4)	0.5366 (3)	0.1942 (2)	0.0749 (11)	0.656 (4)
H27A	−0.0184	0.5762	0.1559	0.090*	0.656 (4)
H27B	0.0469	0.5193	0.2584	0.090*	0.656 (4)
C28	0.1730 (4)	0.6205 (3)	0.1681 (3)	0.0867 (15)	0.656 (4)
H28A	0.1966	0.6409	0.1032	0.104*	0.656 (4)
H28B	0.2673	0.5799	0.2047	0.104*	0.656 (4)
C29	0.0917 (4)	0.7363 (3)	0.1854 (3)	0.131 (3)	0.656 (4)
H29A	0.0013	0.7809	0.1454	0.158*	0.656 (4)
H29B	0.0622	0.7163	0.2494	0.158*	0.656 (4)
C30	0.2013 (6)	0.8128 (4)	0.1645 (4)	0.167 (4)	0.656 (4)
H30A	0.2968	0.7652	0.1987	0.201*	0.656 (4)
H30B	0.2203	0.8424	0.0988	0.201*	0.656 (4)
C31	0.1251 (9)	0.9181 (5)	0.1947 (5)	0.194 (4)	0.656 (4)
H31A	0.0851	0.9904	0.1411	0.291*	0.656 (4)
H31B	0.1976	0.9313	0.2275	0.291*	0.656 (4)
H31C	0.0441	0.8994	0.2346	0.291*	0.656 (4)
C27'	0.1072 (4)	0.5322 (3)	0.2057 (2)	0.0749 (11)	0.344 (4)
H27C	0.0193	0.5294	0.2439	0.090*	0.344 (4)
H27D	0.1882	0.5305	0.2425	0.090*	0.344 (4)
C28'	0.0690 (7)	0.6517 (3)	0.1229 (2)	0.0867 (15)	0.344 (4)
H28C	0.0012	0.6481	0.0803	0.104*	0.344 (4)
H28D	0.1611	0.6620	0.0909	0.104*	0.344 (4)
C29'	−0.0053 (5)	0.7624 (3)	0.1489 (5)	0.131 (3)	0.344 (4)
H29C	−0.0661	0.8272	0.0962	0.158*	0.344 (4)
H29D	−0.0725	0.7406	0.1994	0.158*	0.344 (4)
C30'	0.1095 (5)	0.8093 (4)	0.1779 (3)	0.167 (4)	0.344 (4)
H30C	0.2039	0.7449	0.1988	0.201*	0.344 (4)
H30D	0.0716	0.8361	0.2285	0.201*	0.344 (4)
C31'	0.1362 (10)	0.9185 (5)	0.0923 (4)	0.194 (4)	0.344 (4)
H31D	0.2024	0.8876	0.0509	0.291*	0.344 (4)
H31E	0.1814	0.9654	0.1128	0.291*	0.344 (4)
H31F	0.0410	0.9693	0.0604	0.291*	0.344 (4)
S1	0.54961 (8)	0.43367 (6)	0.36166 (5)	0.0514 (2)
S2	0.20704 (10)	0.42399 (7)	0.07217 (5)	0.0710 (3)
F1	0.0147 (2)	0.34601 (17)	0.51006 (14)	0.0894 (6)
F2	0.2160 (2)	0.19831 (18)	0.57122 (12)	0.0842 (6)
F3	−0.0882 (2)	0.16734 (18)	0.52584 (13)	0.0860 (6)
F4	0.1357 (2)	0.04837 (16)	0.52485 (12)	0.0781 (5)
F5	−0.10646 (19)	0.26982 (19)	0.34769 (14)	0.0889 (6)
F6	0.0564 (2)	0.10029 (17)	0.35752 (12)	0.0806 (6)
N1	0.4135 (3)	0.9211 (3)	0.3802 (2)	0.0910 (9)
N2	0.7517 (4)	0.6262 (3)	0.3236 (2)	0.0990 (11)
N3	0.3212 (8)	0.4646 (4)	−0.1383 (3)	0.196 (3)
N4	0.4655 (6)	0.0932 (4)	−0.1258 (3)	0.1448 (17)
C1	0.3935 (3)	0.5249 (2)	0.39481 (17)	0.0466 (6)
C2	0.2763 (3)	0.4737 (2)	0.41302 (18)	0.0500 (6)
H2	0.1835	0.5082	0.4336	0.060*
C3	0.3096 (3)	0.3639 (2)	0.39761 (17)	0.0437 (6)
C4	0.4564 (3)	0.3291 (2)	0.37081 (17)	0.0465 (6)
C5	0.3828 (3)	0.6419 (2)	0.39756 (18)	0.0526 (7)
H5	0.2916	0.6792	0.4180	0.063*
C6	0.4850 (3)	0.7060 (2)	0.37493 (19)	0.0539 (7)
C7	0.4460 (4)	0.8257 (3)	0.3782 (2)	0.0650 (8)
C8	0.6336 (4)	0.6618 (3)	0.3462 (2)	0.0644 (8)
C9	0.5377 (3)	0.2175 (2)	0.35038 (19)	0.0522 (7)
H9A	0.4696	0.1681	0.3591	0.063*
H9B	0.6228	0.1695	0.3943	0.063*
C10	0.5954 (3)	0.2476 (3)	0.2522 (2)	0.0571 (7)
H10A	0.5106	0.2977	0.2085	0.069*
H10B	0.6657	0.2950	0.2442	0.069*
C11	0.6736 (4)	0.1358 (3)	0.2297 (2)	0.0733 (9)
H11A	0.6025	0.0894	0.2363	0.088*
H11B	0.7569	0.0847	0.2743	0.088*
C12	0.7343 (4)	0.1656 (4)	0.1326 (3)	0.1010 (13)
H12A	0.6530	0.2225	0.0881	0.121*
H12B	0.7681	0.0916	0.1195	0.121*
C13	0.8651 (5)	0.2208 (5)	0.1202 (3)	0.1263 (17)
H13A	0.8292	0.2993	0.1252	0.190*
H13B	0.9061	0.2298	0.0602	0.190*
H13C	0.9425	0.1681	0.1673	0.190*
C14	0.1988 (3)	0.2956 (2)	0.40680 (18)	0.0445 (6)
C15	0.1214 (3)	0.2522 (3)	0.4965 (2)	0.0559 (7)
C16	0.0456 (3)	0.1631 (3)	0.4854 (2)	0.0574 (7)
C17	0.0347 (3)	0.1976 (3)	0.3810 (2)	0.0544 (7)
C18	0.1484 (3)	0.2668 (2)	0.34216 (18)	0.0464 (6)
C19	0.1554 (3)	0.4183 (3)	0.1815 (2)	0.0598 (7)
C20	0.1843 (3)	0.2997 (2)	0.24345 (18)	0.0469 (6)
C21	0.2443 (3)	0.2151 (3)	0.20115 (19)	0.0535 (7)
H21	0.2675	0.1312	0.2333	0.064*
C22	0.2660 (3)	0.2670 (3)	0.10778 (19)	0.0556 (7)
C23	0.3278 (4)	0.2002 (3)	0.0501 (2)	0.0680 (8)
H23	0.3486	0.1159	0.0792	0.082*
C24	0.3606 (4)	0.2403 (3)	−0.0400 (2)	0.0749 (9)
C25	0.3391 (6)	0.3645 (5)	−0.0945 (3)	0.1073 (15)
C26	0.4192 (5)	0.1571 (4)	−0.0867 (3)	0.1014 (13)

	U11	U22	U33	U12	U13	U23
C27	0.087 (3)	0.0505 (19)	0.069 (2)	−0.0050 (18)	0.001 (2)	−0.0136 (17)
C28	0.114 (5)	0.063 (3)	0.075 (4)	−0.030 (3)	0.000 (3)	−0.013 (3)
C29	0.144 (7)	0.054 (3)	0.185 (7)	−0.022 (4)	−0.012 (5)	−0.034 (4)
C30	0.185 (10)	0.104 (4)	0.209 (7)	−0.039 (5)	−0.068 (7)	−0.043 (4)
C31	0.251 (10)	0.113 (6)	0.232 (10)	−0.054 (6)	−0.027 (9)	−0.071 (6)
C27'	0.087 (3)	0.0505 (19)	0.069 (2)	−0.0050 (18)	0.001 (2)	−0.0136 (17)
C28'	0.114 (5)	0.063 (3)	0.075 (4)	−0.030 (3)	0.000 (3)	−0.013 (3)
C29'	0.144 (7)	0.054 (3)	0.185 (7)	−0.022 (4)	−0.012 (5)	−0.034 (4)
C30'	0.185 (10)	0.104 (4)	0.209 (7)	−0.039 (5)	−0.068 (7)	−0.043 (4)
C31'	0.251 (10)	0.113 (6)	0.232 (10)	−0.054 (6)	−0.027 (9)	−0.071 (6)
S1	0.0473 (4)	0.0541 (4)	0.0602 (4)	−0.0221 (3)	0.0138 (3)	−0.0261 (3)
S2	0.0899 (6)	0.0579 (5)	0.0512 (5)	−0.0162 (4)	0.0068 (4)	−0.0101 (4)
F1	0.0933 (14)	0.0817 (13)	0.1140 (16)	−0.0381 (11)	0.0594 (12)	−0.0601 (12)
F2	0.1018 (14)	0.1093 (15)	0.0517 (11)	−0.0604 (12)	0.0066 (10)	−0.0190 (10)
F3	0.0751 (12)	0.1088 (15)	0.0979 (14)	−0.0552 (11)	0.0483 (11)	−0.0512 (12)
F4	0.0929 (14)	0.0567 (11)	0.0743 (12)	−0.0259 (10)	0.0056 (10)	−0.0104 (9)
F5	0.0490 (10)	0.1086 (16)	0.0957 (14)	−0.0291 (11)	−0.0027 (10)	−0.0177 (12)
F6	0.1067 (15)	0.0806 (13)	0.0835 (13)	−0.0619 (11)	0.0303 (11)	−0.0410 (11)
N1	0.095 (2)	0.0611 (19)	0.126 (3)	−0.0279 (17)	0.0086 (19)	−0.0414 (18)
N2	0.087 (2)	0.115 (3)	0.134 (3)	−0.057 (2)	0.047 (2)	−0.076 (2)
N3	0.404 (9)	0.111 (3)	0.085 (3)	−0.110 (5)	0.091 (4)	−0.040 (3)
N4	0.207 (5)	0.112 (3)	0.085 (3)	0.006 (3)	0.019 (3)	−0.045 (2)
C1	0.0509 (15)	0.0456 (15)	0.0456 (15)	−0.0158 (12)	0.0087 (12)	−0.0194 (12)
C2	0.0470 (15)	0.0519 (16)	0.0545 (16)	−0.0164 (13)	0.0133 (12)	−0.0241 (13)
C3	0.0435 (14)	0.0443 (14)	0.0449 (14)	−0.0172 (12)	0.0094 (11)	−0.0163 (12)
C4	0.0473 (15)	0.0478 (15)	0.0453 (15)	−0.0180 (12)	0.0088 (12)	−0.0166 (12)
C5	0.0564 (17)	0.0524 (16)	0.0495 (16)	−0.0170 (14)	0.0057 (13)	−0.0194 (13)
C6	0.0642 (18)	0.0518 (17)	0.0502 (16)	−0.0238 (15)	0.0040 (14)	−0.0189 (13)
C7	0.069 (2)	0.056 (2)	0.073 (2)	−0.0264 (16)	0.0053 (16)	−0.0214 (16)
C8	0.075 (2)	0.067 (2)	0.069 (2)	−0.0396 (18)	0.0200 (17)	−0.0336 (17)
C9	0.0472 (15)	0.0509 (16)	0.0614 (17)	−0.0162 (13)	0.0104 (13)	−0.0240 (14)
C10	0.0470 (16)	0.0665 (19)	0.0635 (18)	−0.0164 (14)	0.0082 (13)	−0.0315 (15)
C11	0.0623 (19)	0.083 (2)	0.093 (2)	−0.0200 (17)	0.0190 (18)	−0.056 (2)
C12	0.073 (2)	0.154 (4)	0.098 (3)	−0.020 (3)	0.015 (2)	−0.081 (3)
C13	0.120 (4)	0.169 (5)	0.098 (3)	−0.049 (3)	0.045 (3)	−0.061 (3)
C14	0.0406 (14)	0.0417 (14)	0.0501 (15)	−0.0137 (11)	0.0121 (11)	−0.0165 (12)
C15	0.0564 (17)	0.0581 (18)	0.0546 (17)	−0.0215 (15)	0.0159 (14)	−0.0216 (14)
C16	0.0505 (17)	0.0591 (19)	0.0659 (19)	−0.0257 (15)	0.0185 (14)	−0.0224 (15)
C17	0.0479 (16)	0.0557 (17)	0.0636 (18)	−0.0227 (14)	0.0120 (14)	−0.0225 (15)
C18	0.0398 (14)	0.0421 (14)	0.0556 (16)	−0.0130 (12)	0.0082 (12)	−0.0166 (13)
C19	0.0637 (18)	0.0515 (17)	0.0560 (17)	−0.0141 (14)	0.0057 (14)	−0.0136 (14)
C20	0.0442 (14)	0.0505 (16)	0.0474 (15)	−0.0171 (12)	0.0048 (12)	−0.0178 (13)
C21	0.0552 (17)	0.0506 (16)	0.0534 (17)	−0.0189 (13)	0.0037 (13)	−0.0157 (13)
C22	0.0589 (17)	0.0581 (18)	0.0500 (17)	−0.0190 (14)	0.0046 (13)	−0.0193 (14)
C23	0.077 (2)	0.064 (2)	0.059 (2)	−0.0168 (17)	0.0060 (16)	−0.0230 (16)
C24	0.089 (2)	0.073 (2)	0.058 (2)	−0.0186 (19)	0.0077 (18)	−0.0249 (18)
C25	0.177 (5)	0.097 (3)	0.061 (2)	−0.059 (3)	0.040 (3)	−0.037 (2)
C26	0.136 (4)	0.092 (3)	0.060 (2)	−0.011 (3)	0.012 (2)	−0.028 (2)

C27—C28	1.504 (2)	N3—C25	1.133 (5)
C27—C19	1.513 (4)	N4—C26	1.142 (5)
C27—H27A	0.9700	C1—C2	1.370 (4)
C27—H27B	0.9700	C1—C5	1.438 (3)
C28—C29	1.520 (2)	C2—C3	1.410 (3)
C28—H28A	0.9700	C2—H2	0.9300
C28—H28B	0.9700	C3—C4	1.380 (3)
C29—C30	1.520 (2)	C3—C14	1.477 (3)
C29—H29A	0.9700	C4—C9	1.501 (3)
C29—H29B	0.9700	C5—C6	1.350 (4)
C30—C31	1.510 (2)	C5—H5	0.9300
C30—H30A	0.9700	C6—C8	1.426 (4)
C30—H30B	0.9700	C6—C7	1.437 (4)
C31—H31A	0.9600	C9—C10	1.524 (4)
C31—H31B	0.9600	C9—H9A	0.9700
C31—H31C	0.9600	C9—H9B	0.9700
C27'—C28'	1.514 (2)	C10—C11	1.514 (4)
C27'—C19	1.527 (4)	C10—H10A	0.9700
C27'—H27C	0.9700	C10—H10B	0.9700
C27'—H27D	0.9700	C11—C12	1.520 (5)
C28'—C29'	1.527 (2)	C11—H11A	0.9700
C28'—H28C	0.9700	C11—H11B	0.9700
C28'—H28D	0.9700	C12—C13	1.523 (6)
C29'—C30'	1.519 (2)	C12—H12A	0.9700
C29'—H29C	0.9700	C12—H12B	0.9700
C29'—H29D	0.9700	C13—H13A	0.9600
C30'—C31'	1.564 (2)	C13—H13B	0.9600
C30'—H30C	0.9700	C13—H13C	0.9600
C30'—H30D	0.9700	C14—C18	1.344 (4)
C31'—H31D	0.9600	C14—C15	1.503 (3)
C31'—H31E	0.9600	C15—C16	1.536 (4)
C31'—H31F	0.9600	C16—C17	1.521 (4)
S1—C4	1.714 (3)	C17—C18	1.498 (3)
S1—C1	1.728 (3)	C18—C20	1.473 (4)
S2—C19	1.715 (3)	C19—C20	1.376 (4)
S2—C22	1.727 (3)	C20—C21	1.399 (4)
F1—C15	1.357 (3)	C21—C22	1.376 (4)
F2—C15	1.340 (3)	C21—H21	0.9300
F3—C16	1.341 (3)	C22—C23	1.421 (4)
F4—C16	1.344 (3)	C23—C24	1.345 (4)
F5—C17	1.356 (3)	C23—H23	0.9300
F6—C17	1.343 (3)	C24—C25	1.406 (5)
N1—C7	1.140 (4)	C24—C26	1.435 (5)
N2—C8	1.133 (4)
C28—C27—C19	110.7 (2)	C4—C9—C10	112.9 (2)
C28—C27—H27A	109.5	C4—C9—H9A	109.0
C19—C27—H27A	109.5	C10—C9—H9A	109.0
C28—C27—H27B	109.5	C4—C9—H9B	109.0
C19—C27—H27B	109.5	C10—C9—H9B	109.0
H27A—C27—H27B	108.1	H9A—C9—H9B	107.8
C27—C28—C29	109.8	C11—C10—C9	113.5 (2)
C27—C28—H28A	109.7	C11—C10—H10A	108.9
C29—C28—H28A	109.7	C9—C10—H10A	108.9
C27—C28—H28B	109.7	C11—C10—H10B	108.9
C29—C28—H28B	109.7	C9—C10—H10B	108.9
H28A—C28—H28B	108.2	H10A—C10—H10B	107.7
C30—C29—C28	107.2	C10—C11—C12	113.6 (3)
C30—C29—H29A	110.3	C10—C11—H11A	108.8
C28—C29—H29A	110.3	C12—C11—H11A	108.8
C30—C29—H29B	110.3	C10—C11—H11B	108.8
C28—C29—H29B	110.3	C12—C11—H11B	108.8
H29A—C29—H29B	108.5	H11A—C11—H11B	107.7
C31—C30—C29	105.7	C11—C12—C13	112.8 (3)
C31—C30—H30A	110.6	C11—C12—H12A	109.0
C29—C30—H30A	110.6	C13—C12—H12A	109.0
C31—C30—H30B	110.6	C11—C12—H12B	109.0
C29—C30—H30B	110.6	C13—C12—H12B	109.0
H30A—C30—H30B	108.7	H12A—C12—H12B	107.8
C28'—C27'—C19	114.7 (3)	C12—C13—H13A	109.5
C28'—C27'—H27C	108.6	C12—C13—H13B	109.5
C19—C27'—H27C	108.6	H13A—C13—H13B	109.5
C28'—C27'—H27D	108.6	C12—C13—H13C	109.5
C19—C27'—H27D	108.6	H13A—C13—H13C	109.5
H27C—C27'—H27D	107.6	H13B—C13—H13C	109.5
C27'—C28'—C29'	113.3	C18—C14—C3	128.6 (2)
C27'—C28'—H28C	108.9	C18—C14—C15	110.7 (2)
C29'—C28'—H28C	108.9	C3—C14—C15	120.6 (2)
C27'—C28'—H28D	108.9	F2—C15—F1	106.4 (2)
C29'—C28'—H28D	108.9	F2—C15—C14	113.5 (2)
H28C—C28'—H28D	107.7	F1—C15—C14	111.3 (2)
C30'—C29'—C28'	112.6	F2—C15—C16	111.3 (2)
C30'—C29'—H29C	109.1	F1—C15—C16	109.8 (2)
C28'—C29'—H29C	109.1	C14—C15—C16	104.5 (2)
C30'—C29'—H29D	109.1	F3—C16—F4	107.2 (2)
C28'—C29'—H29D	109.1	F3—C16—C17	113.5 (2)
H29C—C29'—H29D	107.8	F4—C16—C17	109.5 (2)
C29'—C30'—C31'	108.2	F3—C16—C15	113.1 (2)
C29'—C30'—H30C	110.1	F4—C16—C15	109.4 (2)
C31'—C30'—H30C	110.1	C17—C16—C15	104.1 (2)
C29'—C30'—H30D	110.1	F6—C17—F5	105.5 (2)
C31'—C30'—H30D	110.1	F6—C17—C18	113.5 (2)
H30C—C30'—H30D	108.4	F5—C17—C18	110.2 (2)
C30'—C31'—H31D	109.5	F6—C17—C16	112.6 (2)
C30'—C31'—H31E	109.5	F5—C17—C16	110.0 (2)
H31D—C31'—H31E	109.5	C18—C17—C16	105.2 (2)
C30'—C31'—H31F	109.5	C14—C18—C20	128.9 (2)
H31D—C31'—H31F	109.5	C14—C18—C17	110.9 (2)
H31E—C31'—H31F	109.5	C20—C18—C17	120.0 (2)
C4—S1—C1	92.33 (12)	C20—C19—C27	130.1 (3)
C19—S2—C22	92.55 (14)	C20—C19—C27'	126.0 (3)
C2—C1—C5	124.0 (2)	C20—C19—S2	111.1 (2)
C2—C1—S1	110.45 (19)	C27—C19—S2	118.4 (2)
C5—C1—S1	125.4 (2)	C27'—C19—S2	122.2 (2)
C1—C2—C3	113.6 (2)	C19—C20—C21	112.4 (2)
C1—C2—H2	123.2	C19—C20—C18	123.2 (2)
C3—C2—H2	123.2	C21—C20—C18	124.3 (2)
C4—C3—C2	112.3 (2)	C22—C21—C20	114.1 (3)
C4—C3—C14	123.9 (2)	C22—C21—H21	122.9
C2—C3—C14	123.8 (2)	C20—C21—H21	122.9
C3—C4—C9	129.2 (2)	C21—C22—C23	124.6 (3)
C3—C4—S1	111.28 (19)	C21—C22—S2	109.7 (2)
C9—C4—S1	119.51 (18)	C23—C22—S2	125.6 (2)
C6—C5—C1	129.8 (3)	C24—C23—C22	129.8 (3)
C6—C5—H5	115.1	C24—C23—H23	115.1
C1—C5—H5	115.1	C22—C23—H23	115.1
C5—C6—C8	123.4 (3)	C23—C24—C25	123.0 (3)
C5—C6—C7	120.1 (3)	C23—C24—C26	121.2 (3)
C8—C6—C7	116.4 (3)	C25—C24—C26	115.8 (3)
N1—C7—C6	179.1 (4)	N3—C25—C24	179.7 (6)
N2—C8—C6	179.7 (4)	N4—C26—C24	178.4 (4)
C19—C27—C28—C29	−177.6 (3)	F4—C16—C17—F6	27.0 (3)
C27—C28—C29—C30	176.0	C15—C16—C17—F6	143.8 (2)
C28—C29—C30—C31	−172.5	F3—C16—C17—F5	24.5 (3)
C19—C27'—C28'—C29'	169.7 (3)	F4—C16—C17—F5	144.2 (2)
C27'—C28'—C29'—C30'	84.1	C15—C16—C17—F5	−98.9 (3)
C28'—C29'—C30'—C31'	97.4	F3—C16—C17—C18	143.1 (2)
C4—S1—C1—C2	0.8 (2)	F4—C16—C17—C18	−97.1 (2)
C4—S1—C1—C5	−175.5 (2)	C15—C16—C17—C18	19.7 (3)
C5—C1—C2—C3	174.4 (2)	C3—C14—C18—C20	−3.0 (5)
S1—C1—C2—C3	−1.9 (3)	C15—C14—C18—C20	174.8 (2)
C1—C2—C3—C4	2.4 (3)	C3—C14—C18—C17	−179.4 (2)
C1—C2—C3—C14	−176.1 (2)	C15—C14—C18—C17	−1.6 (3)
C2—C3—C4—C9	178.2 (3)	F6—C17—C18—C14	−135.4 (3)
C14—C3—C4—C9	−3.3 (4)	F5—C17—C18—C14	106.6 (3)
C2—C3—C4—S1	−1.7 (3)	C16—C17—C18—C14	−11.9 (3)
C14—C3—C4—S1	176.8 (2)	F6—C17—C18—C20	47.8 (3)
C1—S1—C4—C3	0.6 (2)	F5—C17—C18—C20	−70.2 (3)
C1—S1—C4—C9	−179.3 (2)	C16—C17—C18—C20	171.3 (2)
C2—C1—C5—C6	−174.7 (3)	C28—C27—C19—C20	124.9 (4)
S1—C1—C5—C6	1.1 (4)	C28—C27—C19—C27'	47.96 (12)
C1—C5—C6—C8	−2.9 (5)	C28—C27—C19—S2	−62.4 (3)
C1—C5—C6—C7	176.4 (3)	C28'—C27'—C19—C20	−174.6 (3)
C3—C4—C9—C10	121.1 (3)	C28'—C27'—C19—C27	−61.76 (13)
S1—C4—C9—C10	−59.0 (3)	C28'—C27'—C19—S2	15.3 (4)
C4—C9—C10—C11	−178.3 (2)	C22—S2—C19—C20	0.7 (2)
C9—C10—C11—C12	−178.7 (3)	C22—S2—C19—C27	−173.3 (3)
C10—C11—C12—C13	67.7 (4)	C22—S2—C19—C27'	172.2 (3)
C4—C3—C14—C18	−58.3 (4)	C27—C19—C20—C21	171.7 (3)
C2—C3—C14—C18	120.1 (3)	C27'—C19—C20—C21	−172.5 (3)
C4—C3—C14—C15	124.1 (3)	S2—C19—C20—C21	−1.4 (3)
C2—C3—C14—C15	−57.5 (4)	C27—C19—C20—C18	−5.5 (5)
C18—C14—C15—F2	135.8 (3)	C27'—C19—C20—C18	10.3 (5)
C3—C14—C15—F2	−46.2 (3)	S2—C19—C20—C18	−178.6 (2)
C18—C14—C15—F1	−104.1 (3)	C14—C18—C20—C19	−59.7 (4)
C3—C14—C15—F1	73.9 (3)	C17—C18—C20—C19	116.5 (3)
C18—C14—C15—C16	14.3 (3)	C14—C18—C20—C21	123.5 (3)
C3—C14—C15—C16	−167.7 (2)	C17—C18—C20—C21	−60.3 (4)
F2—C15—C16—F3	92.8 (3)	C19—C20—C21—C22	1.7 (3)
F1—C15—C16—F3	−24.7 (3)	C18—C20—C21—C22	178.8 (2)
C14—C15—C16—F3	−144.2 (2)	C20—C21—C22—C23	178.9 (3)
F2—C15—C16—F4	−26.5 (3)	C20—C21—C22—S2	−1.1 (3)
F1—C15—C16—F4	−144.1 (2)	C19—S2—C22—C21	0.2 (2)
C14—C15—C16—F4	96.4 (3)	C19—S2—C22—C23	−179.8 (3)
F2—C15—C16—C17	−143.4 (2)	C21—C22—C23—C24	−176.5 (3)
F1—C15—C16—C17	99.0 (3)	S2—C22—C23—C24	3.6 (5)
C14—C15—C16—C17	−20.5 (3)	C22—C23—C24—C25	1.2 (6)
F3—C16—C17—F6	−92.8 (3)	C22—C23—C24—C26	−178.3 (4)