1,2-Bis[5-(9-ethyl-9H-carbazol-3-yl)-2-methyl-thio-phen-3-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pentene.

The title compound, C(43)H(32)F(6)N(2)S(2), is a new symmetrical photochromic diaryl-ethene derivative with 9-ethyl-carbazol-3-yl substituents. The mol-ecule adopts a photoactive anti-parallel conformation [Irie (2000). Chem. Rev.100, 1685-1716; Kobatake et al. (2002). Chem. Commun. pp. 2804-2805], with a dihedral angle between the mean planes of the two thio-phene rings of 56.23 (6)°. The distance between the two reactive C atoms is 3.497 (3) Å. In the crystal, two mol-ecules are associated through a pair of C-H⋯F inter-molecular hydrogen bonds, forming a centrosymmetric dimer. Dimers are linked by weak π-π inter-actions [centroid-centroid distance = 3.8872 (13) Å], forming chains along the c axis.

Related literature

For a review of diaryl­ethenes, see: Irie (2000 ▶). For related structures, see: Irie et al. (1995 ▶, 2001 ▶); Kobatake et al. (2002 ▶); Takami & Irie et al. (2004 ▶). For a review of carbazole, see: Grigalevicius (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C43H32F6N2S2

M = 754.85

Monoclinic,

a = 14.6687 (7) Å

b = 17.0977 (8) Å

c = 14.0017 (7) Å

β = 95.798 (3)°

V = 3493.7 (3) Å3

Z = 4

Cu Kα radiation

μ = 1.97 mm−1

T = 123 K

0.34 × 0.18 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.687, T max = 0.806

40777 measured reflections

6393 independent reflections

5482 reflections with F 2 > 2σ(F 2)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.139

S = 1.00

6393 reflections

479 parameters

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −0.50 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029539/bv2188sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029539/bv2188Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029539/bv2188Isup3.cml

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

C43H32F6N2S2	F(000) = 1560.00
Mr = 754.85	Dx = 1.435 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 36134 reflections
a = 14.6687 (7) Å	θ = 3.0–68.3°
b = 17.0977 (8) Å	µ = 1.97 mm−1
c = 14.0017 (7) Å	T = 123 K
β = 95.798 (3)°	Plate, blue
V = 3493.7 (3) Å3	0.34 × 0.18 × 0.11 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	5482 reflections with F2 > 2σ(F2)
Detector resolution: 5.00 pixels mm-1	Rint = 0.045
ω scans	θmax = 68.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.687, Tmax = 0.806	k = −20→20
40777 measured reflections	l = −16→16
6393 independent reflections

Refinement on F2	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0796P)2 + 3.7293P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.139	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.90 e Å−3
6393 reflections	Δρmin = −0.50 e Å−3
479 parameters

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
S1	0.22266 (5)	0.77807 (4)	0.34058 (5)	0.03204 (16)
S2	0.20529 (4)	0.90769 (4)	0.72247 (4)	0.02856 (16)
F1	0.28611 (10)	1.07557 (9)	0.27753 (10)	0.0337 (3)
F2	0.42244 (10)	1.03335 (9)	0.32305 (11)	0.0381 (3)
F3	0.28436 (11)	1.17289 (9)	0.41361 (11)	0.0392 (3)
F4	0.43102 (11)	1.17032 (10)	0.40307 (11)	0.0428 (4)
F5	0.33901 (11)	1.13896 (8)	0.58847 (10)	0.0342 (3)
F6	0.46135 (10)	1.07923 (9)	0.55108 (10)	0.0326 (3)
N1	−0.06405 (14)	0.78041 (12)	−0.06739 (15)	0.0268 (4)
N2	0.50050 (14)	0.87561 (12)	1.12292 (14)	0.0252 (4)
C1	0.30629 (15)	0.99316 (13)	0.41816 (16)	0.0217 (4)
C2	0.34231 (16)	1.05578 (14)	0.35643 (17)	0.0243 (4)
C3	0.35960 (17)	1.12687 (14)	0.42239 (17)	0.0263 (5)
C4	0.37050 (16)	1.09033 (14)	0.52264 (17)	0.0243 (5)
C5	0.31915 (15)	1.01445 (13)	0.51163 (16)	0.0214 (4)
C6	0.26821 (16)	0.92071 (14)	0.37434 (17)	0.0236 (4)
C7	0.28281 (17)	0.84660 (14)	0.41198 (18)	0.0281 (5)
C8	0.17827 (16)	0.84749 (14)	0.25868 (17)	0.0260 (5)
C9	0.21055 (16)	0.91970 (14)	0.28574 (17)	0.0241 (4)
C10	0.34286 (19)	0.81983 (15)	0.49802 (19)	0.0335 (5)
C11	0.11541 (16)	0.82652 (14)	0.17425 (17)	0.0249 (5)
C12	0.06121 (16)	0.75866 (14)	0.17428 (17)	0.0268 (5)
C13	−0.00007 (16)	0.73789 (14)	0.09707 (18)	0.0274 (5)
C14	−0.00796 (16)	0.78690 (14)	0.01743 (18)	0.0254 (5)
C15	0.04468 (16)	0.85586 (14)	0.01595 (17)	0.0236 (4)
C16	0.10621 (16)	0.87512 (14)	0.09387 (17)	0.0246 (5)
C17	−0.04857 (16)	0.84348 (14)	−0.12509 (17)	0.0262 (5)
C18	0.01812 (16)	0.89281 (14)	−0.07567 (17)	0.0254 (5)
C19	0.04274 (17)	0.96190 (15)	−0.11862 (18)	0.0296 (5)
C20	0.00271 (19)	0.97990 (16)	−0.20982 (19)	0.0341 (5)
C21	−0.06116 (18)	0.92965 (16)	−0.25817 (19)	0.0339 (6)
C22	−0.08871 (18)	0.86168 (16)	−0.21681 (18)	0.0321 (5)
C23	−0.13082 (18)	0.71836 (16)	−0.0910 (2)	0.0331 (5)
C24	−0.0899 (2)	0.64855 (16)	−0.1365 (2)	0.0391 (6)
C25	0.29322 (16)	0.97565 (13)	0.59806 (16)	0.0217 (4)
C26	0.35396 (16)	0.96925 (13)	0.68333 (16)	0.0233 (4)
C27	0.31788 (16)	0.93281 (13)	0.75725 (17)	0.0229 (4)
C28	0.20781 (16)	0.94502 (14)	0.60858 (17)	0.0261 (5)
C29	0.12464 (17)	0.94189 (17)	0.53832 (18)	0.0318 (5)
C30	0.36117 (16)	0.91630 (13)	0.85442 (17)	0.0234 (4)
C31	0.30891 (17)	0.90623 (14)	0.93247 (17)	0.0255 (5)
C32	0.34847 (17)	0.89227 (14)	1.02435 (17)	0.0254 (5)
C33	0.44370 (17)	0.88832 (13)	1.03932 (16)	0.0232 (4)
C34	0.49780 (16)	0.89756 (13)	0.96205 (16)	0.0228 (4)
C35	0.45622 (17)	0.91139 (13)	0.87016 (17)	0.0237 (4)
C36	0.59047 (17)	0.87628 (13)	1.10144 (17)	0.0254 (5)
C37	0.59257 (16)	0.88950 (13)	1.00191 (17)	0.0238 (4)
C38	0.67583 (17)	0.89345 (15)	0.96312 (18)	0.0285 (5)
C39	0.75581 (17)	0.88401 (15)	1.02312 (19)	0.0315 (5)
C40	0.75293 (18)	0.87091 (16)	1.12114 (19)	0.0341 (5)
C41	0.67171 (18)	0.86625 (15)	1.16179 (18)	0.0305 (5)
C42	0.47018 (19)	0.86212 (15)	1.21760 (17)	0.0290 (5)
C43	0.4644 (2)	0.77700 (17)	1.2437 (2)	0.0450 (7)
H9	0.1960	0.9655	0.2489	0.029*
H10A	0.3375	0.7630	0.5046	0.040*
H10B	0.3240	0.8454	0.5555	0.040*
H10C	0.4066	0.8335	0.4906	0.040*
H12	0.0670	0.7259	0.2294	0.032*
H13	−0.0357	0.6916	0.0983	0.033*
H16	0.1421	0.9213	0.0926	0.030*
H19	0.0863	0.9962	−0.0860	0.036*
H20	0.0189	1.0270	−0.2398	0.041*
H21	−0.0863	0.9427	−0.3214	0.041*
H22	−0.1334	0.8285	−0.2496	0.039*
H23A	−0.1817	0.7393	−0.1356	0.040*
H23B	−0.1567	0.7015	−0.0317	0.040*
H24A	−0.1374	0.6088	−0.1511	0.047*
H24B	−0.0405	0.6268	−0.0921	0.047*
H24C	−0.0653	0.6647	−0.1960	0.047*
H26	0.4149	0.9888	0.6884	0.028*
H29A	0.0748	0.9162	0.5679	0.038*
H29B	0.1383	0.9123	0.4815	0.038*
H29C	0.1061	0.9952	0.5193	0.038*
H31	0.2440	0.9092	0.9214	0.031*
H32	0.3119	0.8855	1.0760	0.030*
H35	0.4925	0.9175	0.8182	0.028*
H38	0.6778	0.9025	0.8964	0.034*
H39	0.8133	0.8865	0.9974	0.038*
H40	0.8089	0.8650	1.1610	0.041*
H41	0.6707	0.8566	1.2285	0.037*
H42A	0.4091	0.8862	1.2198	0.035*
H42B	0.5132	0.8886	1.2663	0.035*
H43A	0.4440	0.7722	1.3079	0.054*
H43B	0.5249	0.7528	1.2431	0.054*
H43C	0.4206	0.7506	1.1970	0.054*

	U11	U22	U33	U12	U13	U23
S1	0.0406 (3)	0.0251 (3)	0.0276 (3)	−0.0005 (2)	−0.0101 (2)	−0.0004 (2)
S2	0.0251 (3)	0.0382 (3)	0.0217 (3)	−0.0050 (2)	−0.0011 (2)	0.0071 (2)
F1	0.0398 (8)	0.0397 (8)	0.0191 (7)	−0.0037 (6)	−0.0086 (6)	0.0084 (6)
F2	0.0342 (8)	0.0433 (8)	0.0394 (9)	0.0045 (6)	0.0168 (7)	0.0049 (6)
F3	0.0533 (9)	0.0322 (8)	0.0310 (8)	0.0156 (7)	−0.0006 (7)	0.0054 (6)
F4	0.0499 (9)	0.0477 (9)	0.0298 (8)	−0.0243 (7)	−0.0007 (7)	0.0087 (6)
F5	0.0527 (9)	0.0269 (7)	0.0232 (7)	−0.0022 (6)	0.0045 (6)	−0.0030 (5)
F6	0.0269 (7)	0.0406 (8)	0.0281 (7)	−0.0080 (6)	−0.0077 (6)	0.0069 (6)
N1	0.0246 (10)	0.0311 (10)	0.0234 (10)	−0.0023 (8)	−0.0044 (8)	−0.0039 (8)
N2	0.0310 (10)	0.0295 (10)	0.0144 (9)	0.0024 (8)	−0.0012 (8)	0.0004 (7)
C1	0.0197 (10)	0.0258 (11)	0.0189 (11)	0.0023 (8)	−0.0020 (8)	0.0019 (9)
C2	0.0209 (11)	0.0331 (12)	0.0183 (11)	0.0031 (9)	−0.0010 (9)	0.0026 (9)
C3	0.0283 (12)	0.0272 (12)	0.0229 (12)	−0.0027 (9)	−0.0004 (9)	0.0062 (9)
C4	0.0251 (11)	0.0289 (12)	0.0177 (11)	−0.0002 (9)	−0.0027 (9)	−0.0001 (9)
C5	0.0196 (10)	0.0249 (11)	0.0189 (11)	0.0020 (8)	−0.0019 (8)	0.0022 (8)
C6	0.0245 (11)	0.0272 (11)	0.0185 (11)	0.0015 (9)	−0.0013 (9)	0.0004 (9)
C7	0.0322 (13)	0.0266 (12)	0.0239 (12)	0.0009 (9)	−0.0054 (10)	−0.0012 (9)
C8	0.0258 (11)	0.0295 (12)	0.0218 (12)	0.0016 (9)	−0.0026 (9)	0.0010 (9)
C9	0.0269 (12)	0.0267 (11)	0.0180 (11)	0.0015 (9)	−0.0011 (9)	0.0003 (9)
C10	0.0382 (14)	0.0282 (12)	0.0312 (14)	0.0046 (10)	−0.0108 (11)	−0.0018 (10)
C11	0.0234 (11)	0.0282 (12)	0.0224 (12)	0.0017 (9)	−0.0014 (9)	−0.0013 (9)
C12	0.0291 (12)	0.0281 (12)	0.0225 (12)	0.0006 (9)	−0.0002 (10)	0.0017 (9)
C13	0.0270 (12)	0.0280 (12)	0.0270 (13)	−0.0037 (9)	0.0011 (10)	−0.0016 (9)
C14	0.0228 (11)	0.0280 (12)	0.0251 (12)	0.0006 (9)	0.0007 (9)	−0.0053 (9)
C15	0.0229 (11)	0.0260 (11)	0.0221 (12)	0.0001 (8)	0.0031 (9)	−0.0018 (9)
C16	0.0237 (11)	0.0248 (11)	0.0250 (12)	−0.0013 (9)	0.0002 (9)	−0.0017 (9)
C17	0.0251 (11)	0.0294 (12)	0.0240 (12)	0.0044 (9)	0.0010 (9)	−0.0041 (9)
C18	0.0249 (11)	0.0293 (12)	0.0219 (12)	0.0037 (9)	0.0026 (9)	−0.0016 (9)
C19	0.0300 (12)	0.0308 (12)	0.0282 (13)	0.0006 (10)	0.0032 (10)	−0.0015 (10)
C20	0.0386 (14)	0.0347 (13)	0.0290 (14)	0.0076 (11)	0.0040 (11)	0.0061 (10)
C21	0.0364 (14)	0.0424 (14)	0.0221 (13)	0.0139 (11)	−0.0007 (11)	0.0024 (11)
C22	0.0291 (12)	0.0405 (14)	0.0255 (13)	0.0076 (10)	−0.0032 (10)	−0.0055 (11)
C23	0.0278 (12)	0.0384 (14)	0.0317 (14)	−0.0070 (10)	−0.0043 (10)	−0.0019 (11)
C24	0.0435 (16)	0.0335 (14)	0.0381 (16)	−0.0071 (11)	−0.0072 (12)	−0.0054 (11)
C25	0.0240 (11)	0.0217 (10)	0.0184 (11)	0.0009 (8)	−0.0028 (9)	0.0007 (8)
C26	0.0247 (11)	0.0261 (11)	0.0182 (11)	−0.0027 (9)	−0.0024 (9)	0.0007 (9)
C27	0.0240 (11)	0.0229 (11)	0.0214 (11)	−0.0013 (8)	−0.0000 (9)	0.0011 (9)
C28	0.0261 (12)	0.0300 (12)	0.0212 (12)	−0.0021 (9)	−0.0017 (9)	0.0025 (9)
C29	0.0244 (12)	0.0454 (15)	0.0245 (13)	−0.0013 (10)	−0.0038 (10)	0.0073 (11)
C30	0.0273 (12)	0.0228 (11)	0.0192 (11)	−0.0004 (9)	−0.0014 (9)	0.0011 (8)
C31	0.0255 (12)	0.0268 (12)	0.0238 (12)	0.0008 (9)	0.0006 (9)	0.0018 (9)
C32	0.0292 (12)	0.0271 (11)	0.0202 (12)	0.0004 (9)	0.0041 (9)	0.0028 (9)
C33	0.0310 (12)	0.0216 (11)	0.0167 (11)	−0.0001 (9)	0.0010 (9)	−0.0002 (8)
C34	0.0275 (12)	0.0225 (10)	0.0179 (11)	0.0001 (8)	−0.0009 (9)	0.0004 (8)
C35	0.0279 (12)	0.0251 (11)	0.0181 (11)	−0.0015 (9)	0.0017 (9)	0.0006 (9)
C36	0.0317 (12)	0.0229 (11)	0.0210 (12)	0.0023 (9)	−0.0004 (10)	−0.0017 (9)
C37	0.0273 (12)	0.0233 (11)	0.0199 (11)	0.0014 (9)	−0.0025 (9)	−0.0012 (9)
C38	0.0322 (13)	0.0329 (12)	0.0198 (12)	0.0025 (10)	−0.0008 (10)	−0.0008 (10)
C39	0.0264 (12)	0.0365 (13)	0.0309 (14)	0.0039 (10)	−0.0008 (10)	−0.0051 (10)
C40	0.0324 (13)	0.0362 (14)	0.0311 (14)	0.0075 (10)	−0.0089 (11)	−0.0053 (11)
C41	0.0361 (13)	0.0337 (13)	0.0195 (12)	0.0049 (10)	−0.0075 (10)	−0.0026 (10)
C42	0.0388 (14)	0.0341 (13)	0.0141 (11)	0.0055 (10)	0.0023 (10)	−0.0026 (9)
C43	0.069 (2)	0.0389 (15)	0.0292 (14)	−0.0049 (14)	0.0183 (14)	0.0001 (11)

S1—C7	1.724 (2)	C30—C31	1.407 (3)
S1—C8	1.731 (2)	C30—C35	1.392 (3)
S2—C27	1.728 (2)	C31—C32	1.378 (3)
S2—C28	1.722 (2)	C32—C33	1.393 (3)
F1—C2	1.353 (2)	C33—C34	1.414 (3)
F2—C2	1.363 (2)	C34—C35	1.387 (3)
F3—C3	1.351 (2)	C34—C37	1.451 (3)
F4—C3	1.334 (3)	C36—C37	1.415 (3)
F5—C4	1.357 (2)	C36—C41	1.400 (3)
F6—C4	1.365 (2)	C37—C38	1.388 (3)
N1—C14	1.379 (3)	C38—C39	1.382 (3)
N1—C17	1.380 (3)	C39—C40	1.395 (3)
N1—C23	1.459 (3)	C40—C41	1.374 (3)
N2—C33	1.384 (2)	C42—C43	1.505 (3)
N2—C36	1.383 (3)	C9—H9	0.950
N2—C42	1.459 (3)	C10—H10A	0.980
C1—C2	1.505 (3)	C10—H10B	0.980
C1—C5	1.353 (3)	C10—H10C	0.980
C1—C6	1.468 (3)	C12—H12	0.950
C2—C3	1.532 (3)	C13—H13	0.950
C3—C4	1.530 (3)	C16—H16	0.950
C4—C5	1.500 (3)	C19—H19	0.950
C5—C25	1.464 (3)	C20—H20	0.950
C6—C7	1.381 (3)	C21—H21	0.950
C6—C9	1.429 (3)	C22—H22	0.950
C7—C10	1.491 (3)	C23—H23A	0.990
C8—C9	1.362 (3)	C23—H23B	0.990
C8—C11	1.468 (3)	C24—H24A	0.980
C11—C12	1.407 (3)	C24—H24B	0.980
C11—C16	1.395 (3)	C24—H24C	0.980
C12—C13	1.381 (3)	C26—H26	0.950
C13—C14	1.390 (3)	C29—H29A	0.980
C14—C15	1.411 (3)	C29—H29B	0.980
C15—C16	1.384 (3)	C29—H29C	0.980
C15—C18	1.448 (3)	C31—H31	0.950
C17—C18	1.418 (3)	C32—H32	0.950
C17—C22	1.393 (3)	C35—H35	0.950
C18—C19	1.390 (3)	C38—H38	0.950
C19—C20	1.385 (3)	C39—H39	0.950
C20—C21	1.395 (3)	C40—H40	0.950
C21—C22	1.377 (3)	C41—H41	0.950
C23—C24	1.506 (3)	C42—H42A	0.990
C25—C26	1.420 (3)	C42—H42B	0.990
C25—C28	1.379 (3)	C43—H43A	0.980
C26—C27	1.360 (3)	C43—H43B	0.980
C27—C30	1.470 (3)	C43—H43C	0.980
C28—C29	1.489 (3)
C7—S1—C8	93.12 (11)	C32—C33—C34	120.7 (2)
C27—S2—C28	93.41 (11)	C33—C34—C35	120.0 (2)
C14—N1—C17	108.79 (19)	C33—C34—C37	106.56 (19)
C14—N1—C23	125.6 (2)	C35—C34—C37	133.4 (2)
C17—N1—C23	125.6 (2)	C30—C35—C34	119.8 (2)
C33—N2—C36	108.73 (19)	N2—C36—C37	109.37 (19)
C33—N2—C42	125.5 (2)	N2—C36—C41	129.8 (2)
C36—N2—C42	125.75 (19)	C37—C36—C41	120.8 (2)
C2—C1—C5	109.96 (19)	C34—C37—C36	106.2 (2)
C2—C1—C6	120.08 (19)	C34—C37—C38	133.8 (2)
C5—C1—C6	129.9 (2)	C36—C37—C38	120.1 (2)
F1—C2—F2	105.41 (18)	C37—C38—C39	118.9 (2)
F1—C2—C1	115.25 (18)	C38—C39—C40	120.6 (2)
F1—C2—C3	110.11 (18)	C39—C40—C41	122.0 (2)
F2—C2—C1	111.20 (18)	C36—C41—C40	117.6 (2)
F2—C2—C3	109.51 (18)	N2—C42—C43	113.8 (2)
C1—C2—C3	105.34 (19)	C6—C9—H9	122.9
F3—C3—F4	107.96 (19)	C8—C9—H9	122.9
F3—C3—C2	108.86 (18)	C7—C10—H10A	109.5
F3—C3—C4	109.3 (2)	C7—C10—H10B	109.5
F4—C3—C2	113.9 (2)	C7—C10—H10C	109.5
F4—C3—C4	113.70 (19)	H10A—C10—H10B	109.5
C2—C3—C4	102.98 (18)	H10A—C10—H10C	109.5
F5—C4—F6	106.05 (17)	H10B—C10—H10C	109.5
F5—C4—C3	111.22 (18)	C11—C12—H12	118.8
F5—C4—C5	113.45 (19)	C13—C12—H12	118.8
F6—C4—C3	109.44 (19)	C12—C13—H13	121.1
F6—C4—C5	112.02 (18)	C14—C13—H13	121.0
C3—C4—C5	104.71 (18)	C11—C16—H16	120.1
C1—C5—C4	110.6 (2)	C15—C16—H16	120.1
C1—C5—C25	130.9 (2)	C18—C19—H19	120.6
C4—C5—C25	118.47 (19)	C20—C19—H19	120.5
C1—C6—C7	125.3 (2)	C19—C20—H20	119.6
C1—C6—C9	122.7 (2)	C21—C20—H20	119.6
C7—C6—C9	112.1 (2)	C20—C21—H21	119.1
S1—C7—C6	110.60 (17)	C22—C21—H21	119.1
S1—C7—C10	119.07 (17)	C17—C22—H22	121.3
C6—C7—C10	130.3 (2)	C21—C22—H22	121.3
S1—C8—C9	109.89 (17)	N1—C23—H23A	109.1
S1—C8—C11	121.97 (17)	N1—C23—H23B	109.1
C9—C8—C11	128.1 (2)	C24—C23—H23A	109.1
C6—C9—C8	114.3 (2)	C24—C23—H23B	109.1
C8—C11—C12	120.7 (2)	H23A—C23—H23B	107.8
C8—C11—C16	120.4 (2)	C23—C24—H24A	109.5
C12—C11—C16	118.9 (2)	C23—C24—H24B	109.5
C11—C12—C13	122.4 (2)	C23—C24—H24C	109.5
C12—C13—C14	117.9 (2)	H24A—C24—H24B	109.5
N1—C14—C13	129.5 (2)	H24A—C24—H24C	109.5
N1—C14—C15	109.5 (2)	H24B—C24—H24C	109.5
C13—C14—C15	120.9 (2)	C25—C26—H26	122.7
C14—C15—C16	120.1 (2)	C27—C26—H26	122.7
C14—C15—C18	106.20 (19)	C28—C29—H29A	109.5
C16—C15—C18	133.7 (2)	C28—C29—H29B	109.5
C11—C16—C15	119.8 (2)	C28—C29—H29C	109.5
N1—C17—C18	108.99 (19)	H29A—C29—H29B	109.5
N1—C17—C22	129.4 (2)	H29A—C29—H29C	109.5
C18—C17—C22	121.6 (2)	H29B—C29—H29C	109.5
C15—C18—C17	106.5 (2)	C30—C31—H31	118.8
C15—C18—C19	134.1 (2)	C32—C31—H31	118.8
C17—C18—C19	119.4 (2)	C31—C32—H32	121.0
C18—C19—C20	118.9 (2)	C33—C32—H32	121.0
C19—C20—C21	120.8 (2)	C30—C35—H35	120.1
C20—C21—C22	121.8 (2)	C34—C35—H35	120.1
C17—C22—C21	117.5 (2)	C37—C38—H38	120.6
N1—C23—C24	112.7 (2)	C39—C38—H38	120.6
C5—C25—C26	122.5 (2)	C38—C39—H39	119.7
C5—C25—C28	125.1 (2)	C40—C39—H39	119.7
C26—C25—C28	112.4 (2)	C39—C40—H40	119.0
C25—C26—C27	114.6 (2)	C41—C40—H40	119.0
S2—C27—C26	109.49 (16)	C36—C41—H41	121.2
S2—C27—C30	121.63 (18)	C40—C41—H41	121.2
C26—C27—C30	128.9 (2)	N2—C42—H42A	108.8
S2—C28—C25	110.14 (16)	N2—C42—H42B	108.8
S2—C28—C29	120.39 (18)	C43—C42—H42A	108.8
C25—C28—C29	129.5 (2)	C43—C42—H42B	108.8
C27—C30—C31	121.6 (2)	H42A—C42—H42B	107.7
C27—C30—C35	119.4 (2)	C42—C43—H43A	109.5
C31—C30—C35	119.0 (2)	C42—C43—H43B	109.5
C30—C31—C32	122.4 (2)	C42—C43—H43C	109.5
C31—C32—C33	118.1 (2)	H43A—C43—H43B	109.5
N2—C33—C32	130.1 (2)	H43A—C43—H43C	109.5
N2—C33—C34	109.2 (2)	H43B—C43—H43C	109.5
C7—S1—C8—C9	1.0 (2)	C9—C6—C7—C10	175.1 (2)
C7—S1—C8—C11	−179.0 (2)	S1—C8—C9—C6	−2.4 (2)
C8—S1—C7—C6	0.7 (2)	S1—C8—C11—C12	25.0 (3)
C8—S1—C7—C10	−176.9 (2)	S1—C8—C11—C16	−157.19 (19)
C27—S2—C28—C25	0.17 (19)	C9—C8—C11—C12	−155.0 (2)
C27—S2—C28—C29	−179.2 (2)	C9—C8—C11—C16	22.8 (3)
C28—S2—C27—C26	0.76 (18)	C11—C8—C9—C6	177.6 (2)
C28—S2—C27—C30	179.51 (19)	C8—C11—C12—C13	178.6 (2)
C14—N1—C17—C18	−1.0 (2)	C8—C11—C16—C15	−178.0 (2)
C14—N1—C17—C22	179.7 (2)	C12—C11—C16—C15	−0.2 (3)
C17—N1—C14—C13	179.4 (2)	C16—C11—C12—C13	0.8 (3)
C17—N1—C14—C15	0.6 (2)	C11—C12—C13—C14	−0.5 (3)
C14—N1—C23—C24	−88.1 (3)	C12—C13—C14—N1	−179.0 (2)
C23—N1—C14—C13	1.2 (4)	C12—C13—C14—C15	−0.3 (3)
C23—N1—C14—C15	−177.6 (2)	N1—C14—C15—C16	179.8 (2)
C17—N1—C23—C24	93.9 (2)	N1—C14—C15—C18	0.0 (2)
C23—N1—C17—C18	177.2 (2)	C13—C14—C15—C16	0.9 (3)
C23—N1—C17—C22	−2.0 (4)	C13—C14—C15—C18	−178.9 (2)
C33—N2—C36—C37	−0.1 (2)	C14—C15—C16—C11	−0.6 (3)
C33—N2—C36—C41	179.9 (2)	C14—C15—C18—C17	−0.7 (2)
C36—N2—C33—C32	179.6 (2)	C14—C15—C18—C19	178.0 (2)
C36—N2—C33—C34	−0.1 (2)	C16—C15—C18—C17	179.6 (2)
C33—N2—C42—C43	96.1 (2)	C16—C15—C18—C19	−1.7 (5)
C42—N2—C33—C32	0.8 (3)	C18—C15—C16—C11	179.1 (2)
C42—N2—C33—C34	−178.9 (2)	N1—C17—C18—C15	1.0 (2)
C36—N2—C42—C43	−82.5 (3)	N1—C17—C18—C19	−177.9 (2)
C42—N2—C36—C37	178.7 (2)	N1—C17—C22—C21	179.2 (2)
C42—N2—C36—C41	−1.3 (3)	C18—C17—C22—C21	0.1 (2)
C2—C1—C5—C4	−3.9 (2)	C22—C17—C18—C15	−179.6 (2)
C2—C1—C5—C25	177.4 (2)	C22—C17—C18—C19	1.5 (3)
C5—C1—C2—F1	−134.0 (2)	C15—C18—C19—C20	−179.9 (2)
C5—C1—C2—F2	106.1 (2)	C17—C18—C19—C20	−1.4 (3)
C5—C1—C2—C3	−12.4 (2)	C18—C19—C20—C21	−0.1 (3)
C2—C1—C6—C7	138.9 (2)	C19—C20—C21—C22	1.7 (4)
C2—C1—C6—C9	−41.0 (3)	C20—C21—C22—C17	−1.6 (4)
C6—C1—C2—F1	48.5 (2)	C5—C25—C26—C27	178.7 (2)
C6—C1—C2—F2	−71.4 (2)	C5—C25—C28—S2	−177.96 (18)
C6—C1—C2—C3	170.05 (19)	C5—C25—C28—C29	1.4 (4)
C5—C1—C6—C7	−38.0 (4)	C26—C25—C28—S2	−1.0 (2)
C5—C1—C6—C9	142.0 (2)	C26—C25—C28—C29	178.3 (2)
C6—C1—C5—C4	173.3 (2)	C28—C25—C26—C27	1.7 (2)
C6—C1—C5—C25	−5.4 (4)	C25—C26—C27—S2	−1.5 (2)
F1—C2—C3—F3	31.7 (2)	C25—C26—C27—C30	179.9 (2)
F1—C2—C3—F4	−88.8 (2)	S2—C27—C30—C31	−23.2 (3)
F1—C2—C3—C4	147.60 (19)	S2—C27—C30—C35	157.56 (18)
F2—C2—C3—F3	147.18 (18)	C26—C27—C30—C31	155.3 (2)
F2—C2—C3—F4	26.7 (2)	C26—C27—C30—C35	−23.9 (3)
F2—C2—C3—C4	−96.9 (2)	C27—C30—C31—C32	−178.7 (2)
C1—C2—C3—F3	−93.1 (2)	C27—C30—C35—C34	178.6 (2)
C1—C2—C3—F4	146.34 (19)	C31—C30—C35—C34	−0.7 (3)
C1—C2—C3—C4	22.7 (2)	C35—C30—C31—C32	0.5 (3)
F3—C3—C4—F5	−32.1 (2)	C30—C31—C32—C33	0.1 (2)
F3—C3—C4—F6	−148.90 (18)	C31—C32—C33—N2	179.6 (2)
F3—C3—C4—C5	90.8 (2)	C31—C32—C33—C34	−0.7 (3)
F4—C3—C4—F5	88.6 (2)	N2—C33—C34—C35	−179.7 (2)
F4—C3—C4—F6	−28.2 (2)	N2—C33—C34—C37	0.3 (2)
F4—C3—C4—C5	−148.48 (19)	C32—C33—C34—C35	0.5 (3)
C2—C3—C4—F5	−147.66 (19)	C32—C33—C34—C37	−179.5 (2)
C2—C3—C4—F6	95.5 (2)	C33—C34—C35—C30	0.1 (2)
C2—C3—C4—C5	−24.8 (2)	C33—C34—C37—C36	−0.4 (2)
F5—C4—C5—C1	140.05 (19)	C33—C34—C37—C38	−179.2 (2)
F5—C4—C5—C25	−41.0 (2)	C35—C34—C37—C36	179.6 (2)
F6—C4—C5—C1	−99.9 (2)	C35—C34—C37—C38	0.8 (4)
F6—C4—C5—C25	79.0 (2)	C37—C34—C35—C30	−179.9 (2)
C3—C4—C5—C1	18.6 (2)	N2—C36—C37—C34	0.3 (2)
C3—C4—C5—C25	−162.5 (2)	N2—C36—C37—C38	179.3 (2)
C1—C5—C25—C26	135.6 (2)	N2—C36—C41—C40	−179.0 (2)
C1—C5—C25—C28	−47.8 (3)	C37—C36—C41—C40	1.0 (3)
C4—C5—C25—C26	−43.1 (3)	C41—C36—C37—C34	−179.7 (2)
C4—C5—C25—C28	133.5 (2)	C41—C36—C37—C38	−0.7 (3)
C1—C6—C7—S1	177.90 (19)	C34—C37—C38—C39	179.0 (2)
C1—C6—C7—C10	−4.9 (4)	C36—C37—C38—C39	0.2 (3)
C1—C6—C9—C8	−177.0 (2)	C37—C38—C39—C40	−0.2 (3)
C7—C6—C9—C8	3.0 (3)	C38—C39—C40—C41	0.5 (4)
C9—C6—C7—S1	−2.1 (2)	C39—C40—C41—C36	−0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···F2i	0.95	2.44	3.290 (2)	149.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯F2i	0.95	2.44	3.290 (2)	149 (1)

Symmetry code: (i) .