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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2311.
Published online 2008 November 13. doi:  10.1107/S1600536808036453
PMCID: PMC2959974

5-n-Butyl-4-[2-(2-ethyl-1-benzothio­phen-3-yl)-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-en-1-yl]thio­phene-2-carbaldehyde

Abstract

The title compound, C24H20F6OS2, exhibiting photochromic behaviour, has thienyl and benzothienyl substituents attached to the double-bond C atoms of the envelope-shaped cyclo­pentene ring. The mean planes of aromatic systems form dihedral angles of 43.0 (1) (thien­yl) and 73.8 (1)° (benzothien­yl) with the mean plane of the C—C=C—C portion of the cyclo­pentene ring. This conformation avoids steric hindrance between the n-butyl and ethyl substituents. The formyl substituent of the thienyl group, as well as the ethyl substituent of the benzothienyl group, are disordered [occupancies of 0.788 (17):0.212 (17) and 0.64 (5):0.36 (5), respectively].

Related literature

For the synthesis of the precursors, see: Pu et al. (2008 [triangle]); Ramamurthy & Venkatesan (1987 [triangle]); Kobatake & Irie (2004 [triangle]); Zheng et al. (2007 [triangle]). For the crystal structures of other photochromic dithienyl-substituted hexa­fluoro­cyclo­pentenes, see: Congbin et al. (2007 [triangle]); Li et al. (2008 [triangle]); Liu et al. (2008 [triangle]); Pu & Zhou (2007 [triangle]); Tu et al. (2008 [triangle]); Zhu et al. (2007 [triangle]).

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Object name is e-64-o2311-scheme1.jpg

Experimental

Crystal data

  • C24H20F6OS2
  • M r = 502.52
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2311-efi1.jpg
  • a = 10.051 (1) Å
  • b = 11.031 (1) Å
  • c = 12.019 (1) Å
  • α = 113.126 (1)°
  • β = 96.882 (1)°
  • γ = 103.542 (1)°
  • V = 1157.5 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 296 (2) K
  • 0.43 × 0.43 × 0.43 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: none
  • 10086 measured reflections
  • 5195 independent reflections
  • 3669 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.151
  • S = 1.03
  • 5195 reflections
  • 318 parameters
  • 30 restraints
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036453/ya2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036453/ya2080Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Foundation of Jiangxi (0620012) and the Science Fund of the Education Office of Jiangxi ([2007]279).

supplementary crystallographic information

Comment

The title compound has thienyl and benzothienyl substituents on the double-bond C atoms of the envelope-shaped cyclopentene ring. The planes of aromatic systems form dihedral angles 43.0 (1)° (thienyl) and 73.8 (1)° (benzothienyl) with the mean plane of the C4–C11=C15–C16 portion of the cyclpentene ring. Such conformation allows to avoid steric hindrance between the n-butyl and ethyl substituents (Fig. 1). The terminal atoms of formyl substituent on the thienyl group as well as the ethyl substituent on the benzothienyl group are disordered over two positions. The intramolecular distance between C3 and C20 is 3.989 (8) Å. This distance indicates that the compound may undergo photochromism in crystalline phase to form the closed ring isomer, as photochromic reactivity was shown to occur when the distance between the potentially reactive C atoms is less than 4.2 Å (Ramamurthy & Venkatesan, 1987; Kobatake & Irie, 2004).

Indeed, crystals of the title compound show photochromism: upon irradiation with 365 nm light, the colourless crystals rapidly turn blue, and the blue crystals turn colourless again upon irradiation with visible light (>510 nm). When dissolved in hexane, the blue compound displays an absorption maximum at 581 nm; the solution of colourless compound has absorption maximum at 257 nm.

Experimental

2.0 mL (5 mmol) of n-butyllithium was added under stirring in nitrogen atmosphere to 30 mL of THF solution containing 1.46 g (5.0 mmol) of 4-bromo-5-n-butyl-2-(1,3-dioxolane)-thiophene (Zheng et al., 2007) at 195 K. 40 min later, 10 mL of THF solution containing 1.77 g (5.0 mmol) of 1-(2-ethyl-1-benzothien-3-yl)heptafluorocyclopentene (Pu et al., 2008) was added to the reaction mixture and stirring under nitrogen atmosphere at 195 K was continued for two more hours. The reaction mixture was extracted with diethyl ether and evaporated in vacuum. Then the obtained compound was hydrolyzed by p-toluenesulfonic acid (0.4 g) in mixture of water (30 ml) and acetone (90 ml). Pyridine (2 ml) was added, and the solution was refluxed for 24 hours and then washed with aqueous sodium bicarbonate. The mixed compound was extracted with diethyl ether and evaporated in vacuum. The crude product was purified by column chromatography on silica, with ethyl acetate and petroleum ether (v/v 1/6) as the eluent, to give 1.58 g (3.15 mmol, 63% yield) of the title compound. Elemental analysis: calc. for C24H20F6OS2: C 57.36, H, 4.01%. Found C 57.22, H 3.90%.

Refinement

All H atoms were positioned geometrically and treated as riding with C—H = 0.97 Å (methylene), 0.96 Å (methyl) or 0.93 Å (aromatic and formyl) with Uiso(H) = 1.2Ueq(C) (Uiso(H) = 1.5Ueq(C) for methyl H atoms).

The methyl group of the ethyl chain is disordered over two sites C1 and C1'; the the C3–C2 distance was restrained to 1.50±0.01 Å, C2–C1 and C2–C1' distances were restrained to be equal within 0.01 Å, and C3···C1 and C3···C1' restrained to 2.51±0.01 Å. The occupancies of the disorder components refined to a 0.79 (1):0.21 ratio.

The formyl oxygen atom is also disordered over two positions; the C19–O1 and C19-O1' distances were restrained to be equal within 0.01 Å. The occupancies of the O1 and O1' atoms refined to a 0.64 (1):0.36 ratio.

The anisotropic displacement parameters of the disordered atoms were restrained to be nearly isotropic.

Figures

Fig. 1.
Molecular structure of the title compound and the atom-labelling scheme; thermal displacement ellipsoids are drawn at the 30% probability level. Minor components of the disorder are shown with the dashed bonds; H atoms are omitted.

Crystal data

C24H20F6OS2Z = 2
Mr = 502.52F000 = 516
Triclinic, P1Dx = 1.442 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.051 (1) ÅCell parameters from 4259 reflections
b = 11.031 (1) Åθ = 2.5–28.2º
c = 12.019 (1) ŵ = 0.29 mm1
α = 113.126 (1)ºT = 296 (2) K
β = 96.882 (1)ºBlock, colourless
γ = 103.542 (1)º0.43 × 0.43 × 0.43 mm
V = 1157.5 (2) Å3

Data collection

Bruker SMART area-detector diffractometer3669 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Monochromator: graphiteθmax = 27.5º
T = 296(2) Kθmin = 2.5º
[var phi] and ω scansh = −12→13
Absorption correction: Nonek = −14→14
10086 measured reflectionsl = −15→15
5195 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.151  w = 1/[σ2(Fo2) + (0.0768P)2 + 0.3784P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5195 reflectionsΔρmax = 0.34 e Å3
318 parametersΔρmin = −0.25 e Å3
30 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
S10.43383 (7)0.52869 (8)0.19023 (8)0.0736 (2)
S20.86262 (7)0.60297 (6)0.65571 (5)0.05353 (19)
F10.89175 (19)0.80884 (18)0.17554 (17)0.0805 (5)
F20.8985 (2)0.6035 (2)0.06303 (14)0.0868 (6)
F31.16124 (19)0.8540 (2)0.22574 (18)0.0943 (6)
F41.1390 (2)0.6431 (2)0.19936 (18)0.0921 (6)
F51.10459 (17)0.92568 (14)0.44135 (15)0.0707 (4)
F61.19297 (14)0.76341 (19)0.43741 (16)0.0735 (5)
O1'0.947 (3)0.8292 (9)0.9172 (7)0.091 (4)0.64 (5)
O11.010 (3)0.8304 (18)0.9249 (10)0.080 (4)0.36 (5)
C10.5164 (7)0.8436 (7)0.3633 (7)0.104 (3)0.788 (17)
H1A0.54760.93700.42760.156*0.788 (17)
H1B0.44030.78890.38120.156*0.788 (17)
H1C0.48480.84350.28460.156*0.788 (17)
C1'0.577 (3)0.8783 (13)0.3189 (17)0.077 (6)0.212 (17)
H1'A0.60290.96820.38800.116*0.212 (17)
H1'B0.47670.84140.29100.116*0.212 (17)
H1'C0.61690.88610.25220.116*0.212 (17)
C20.6323 (4)0.7854 (3)0.3580 (3)0.0885 (10)
H2A0.66460.79000.43930.106*
H2B0.70920.84460.34330.106*
C30.6050 (3)0.6395 (3)0.2628 (2)0.0565 (6)
C40.7027 (2)0.5769 (2)0.2221 (2)0.0454 (5)
C50.6422 (3)0.4353 (2)0.1294 (2)0.0519 (6)
C60.7084 (3)0.3380 (3)0.0696 (2)0.0677 (7)
H60.80610.36270.08410.081*
C70.6267 (5)0.2048 (3)−0.0111 (3)0.0914 (11)
H70.67030.1400−0.05170.110*
C80.4127 (4)0.2581 (4)0.0223 (3)0.0846 (10)
H80.31490.23150.00580.102*
C90.4813 (5)0.1652 (4)−0.0332 (3)0.0991 (13)
H90.42920.0739−0.08670.119*
C100.4937 (3)0.3945 (3)0.1048 (2)0.0615 (7)
C110.8549 (2)0.6521 (2)0.2655 (2)0.0424 (5)
C120.9296 (3)0.6987 (3)0.1805 (2)0.0560 (6)
C131.0846 (3)0.7499 (3)0.2438 (2)0.0576 (6)
C141.0847 (2)0.7868 (2)0.3798 (2)0.0480 (5)
C150.9421 (2)0.7024 (2)0.37843 (19)0.0387 (4)
C160.9193 (2)0.6924 (2)0.49357 (19)0.0385 (4)
C170.9764 (2)0.8081 (2)0.6132 (2)0.0467 (5)
H171.02470.89660.62450.056*
C180.9532 (3)0.7762 (2)0.7089 (2)0.0533 (6)
C190.9934 (4)0.8673 (3)0.8416 (3)0.0801 (9)
H191.05520.95620.87020.096*0.64 (5)
H19'1.00750.96130.86540.096*0.36 (5)
C200.8536 (2)0.5729 (2)0.50312 (19)0.0401 (4)
C210.7831 (2)0.4277 (2)0.4049 (2)0.0425 (5)
H21A0.82960.36680.42160.051*
H21B0.79490.42380.32470.051*
C220.6266 (2)0.3746 (2)0.3974 (2)0.0510 (5)
H22A0.61390.38790.47960.061*
H22B0.57820.42890.37130.061*
C230.5601 (3)0.2226 (3)0.3076 (3)0.0634 (7)
H23A0.60270.16750.33780.076*
H23B0.58000.20770.22710.076*
C240.4014 (4)0.1731 (4)0.2918 (3)0.0940 (11)
H24A0.36480.07660.23460.141*
H24B0.35830.22550.25980.141*
H24C0.38100.18600.37090.141*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0440 (4)0.0835 (5)0.0917 (6)0.0164 (3)−0.0006 (3)0.0430 (4)
S20.0674 (4)0.0499 (3)0.0462 (3)0.0127 (3)0.0157 (3)0.0262 (3)
F10.0839 (11)0.0906 (12)0.0950 (12)0.0251 (9)0.0131 (9)0.0717 (11)
F20.0934 (13)0.0972 (13)0.0451 (9)−0.0039 (10)0.0150 (8)0.0255 (9)
F30.0792 (12)0.1137 (15)0.0913 (13)−0.0117 (10)0.0169 (10)0.0701 (12)
F40.0853 (12)0.1121 (15)0.0909 (13)0.0522 (11)0.0407 (10)0.0382 (12)
F50.0776 (10)0.0444 (8)0.0744 (10)−0.0017 (7)0.0125 (8)0.0233 (7)
F60.0408 (7)0.1085 (13)0.0919 (11)0.0184 (8)0.0082 (7)0.0688 (11)
O1'0.127 (8)0.085 (3)0.047 (2)0.009 (4)0.025 (3)0.0263 (19)
O10.107 (9)0.084 (5)0.053 (4)0.032 (5)0.015 (4)0.033 (3)
C10.098 (4)0.102 (4)0.114 (4)0.061 (3)0.027 (3)0.031 (3)
C1'0.082 (10)0.072 (8)0.084 (9)0.033 (7)0.013 (6)0.036 (6)
C20.080 (2)0.0667 (19)0.102 (2)0.0363 (16)0.0055 (18)0.0168 (18)
C30.0474 (13)0.0579 (14)0.0639 (15)0.0171 (11)0.0035 (11)0.0285 (12)
C40.0462 (12)0.0475 (12)0.0416 (11)0.0112 (9)0.0022 (9)0.0226 (10)
C50.0569 (14)0.0512 (13)0.0419 (12)0.0071 (10)0.0020 (10)0.0228 (10)
C60.0835 (19)0.0575 (15)0.0530 (15)0.0147 (14)0.0191 (14)0.0182 (12)
C70.128 (3)0.0590 (18)0.0636 (19)0.0153 (19)0.028 (2)0.0098 (15)
C80.077 (2)0.075 (2)0.0695 (19)−0.0144 (17)−0.0182 (16)0.0302 (17)
C90.126 (3)0.062 (2)0.063 (2)−0.012 (2)−0.001 (2)0.0117 (16)
C100.0552 (14)0.0627 (15)0.0549 (14)0.0001 (12)−0.0070 (11)0.0298 (12)
C110.0446 (11)0.0412 (11)0.0440 (11)0.0122 (9)0.0084 (9)0.0225 (9)
C120.0625 (15)0.0605 (14)0.0468 (13)0.0110 (12)0.0099 (11)0.0308 (12)
C130.0538 (14)0.0631 (15)0.0651 (16)0.0132 (12)0.0200 (12)0.0381 (13)
C140.0416 (11)0.0476 (12)0.0573 (14)0.0091 (9)0.0057 (10)0.0296 (11)
C150.0392 (10)0.0366 (10)0.0445 (11)0.0130 (8)0.0096 (8)0.0213 (9)
C160.0366 (10)0.0395 (10)0.0430 (11)0.0134 (8)0.0057 (8)0.0215 (9)
C170.0537 (12)0.0384 (11)0.0466 (12)0.0122 (9)0.0082 (10)0.0192 (9)
C180.0645 (15)0.0470 (12)0.0453 (12)0.0153 (11)0.0112 (11)0.0186 (10)
C190.126 (3)0.0564 (16)0.0457 (15)0.0148 (17)0.0188 (16)0.0175 (13)
C200.0404 (10)0.0419 (11)0.0431 (11)0.0151 (8)0.0092 (9)0.0224 (9)
C210.0455 (11)0.0382 (10)0.0476 (12)0.0153 (9)0.0087 (9)0.0218 (9)
C220.0471 (12)0.0458 (12)0.0566 (14)0.0088 (10)0.0090 (10)0.0229 (11)
C230.0630 (16)0.0483 (13)0.0684 (17)0.0043 (12)0.0049 (13)0.0253 (12)
C240.073 (2)0.079 (2)0.091 (2)−0.0168 (17)0.0107 (17)0.0238 (18)

Geometric parameters (Å, °)

S1—C101.726 (3)C7—H70.9300
S1—C31.742 (3)C8—C91.369 (5)
S2—C201.717 (2)C8—C101.403 (4)
S2—C181.725 (2)C8—H80.9300
F1—C121.376 (3)C9—H90.9300
F2—C121.331 (3)C11—C151.346 (3)
F3—C131.335 (3)C11—C121.512 (3)
F4—C131.360 (3)C12—C131.513 (4)
F5—C141.366 (3)C13—C141.521 (3)
F6—C141.350 (3)C14—C151.510 (3)
O1'—C191.236 (5)C15—C161.471 (3)
O1—C191.228 (8)C16—C201.385 (3)
C1—C21.453 (5)C16—C171.430 (3)
C1—H1A0.9600C17—C181.358 (3)
C1—H1B0.9600C17—H170.9300
C1—H1C0.9600C18—C191.453 (4)
C1'—C21.468 (8)C19—H190.9300
C1'—H1'A0.9600C19—H19'0.9300
C1'—H1'B0.9600C20—C211.497 (3)
C1'—H1'C0.9600C21—C221.523 (3)
C2—C31.499 (4)C21—H21A0.9700
C2—H2A0.9700C21—H21B0.9700
C2—H2B0.9700C22—C231.518 (3)
C3—C41.359 (3)C22—H22A0.9700
C4—C51.441 (3)C22—H22B0.9700
C4—C111.475 (3)C23—C241.522 (4)
C5—C61.399 (4)C23—H23A0.9700
C5—C101.412 (4)C23—H23B0.9700
C6—C71.378 (4)C24—H24A0.9600
C6—H60.9300C24—H24B0.9600
C7—C91.384 (6)C24—H24C0.9600
C10—S1—C391.85 (12)F4—C13—C12108.6 (2)
C20—S2—C1892.17 (11)F3—C13—C14113.6 (2)
C2—C1—H1A109.5F4—C13—C14108.9 (2)
C2—C1—H1B109.5C12—C13—C14103.50 (19)
H1A—C1—H1B109.5F6—C14—F5105.70 (19)
C2—C1—H1C109.5F6—C14—C15113.35 (17)
H1A—C1—H1C109.5F5—C14—C15111.64 (19)
H1B—C1—H1C109.5F6—C14—C13111.9 (2)
C2—C1'—H1'A109.5F5—C14—C13108.90 (18)
C2—C1'—H1'B109.5C15—C14—C13105.39 (18)
H1'A—C1'—H1'B109.5C11—C15—C16131.72 (19)
C2—C1'—H1'C109.5C11—C15—C14109.62 (18)
H1'A—C1'—H1'C109.5C16—C15—C14118.62 (18)
H1'B—C1'—H1'C109.5C20—C16—C17111.60 (18)
C1—C2—C3117.8 (3)C20—C16—C15126.15 (19)
C1'—C2—C3117.9 (6)C17—C16—C15122.02 (18)
C1—C2—H2A107.9C18—C17—C16113.4 (2)
C1'—C2—H2A132.3C18—C17—H17123.3
C3—C2—H2A107.9C16—C17—H17123.3
C1—C2—H2B107.9C17—C18—C19128.5 (2)
C3—C2—H2B107.9C17—C18—S2111.32 (18)
H2A—C2—H2B107.2C19—C18—S2120.2 (2)
C4—C3—C2127.0 (2)O1—C19—C18125.4 (8)
C4—C3—S1111.98 (18)O1'—C19—C18121.5 (5)
C2—C3—S1121.0 (2)O1—C19—H19107.4
C3—C4—C5113.4 (2)O1'—C19—H19119.3
C3—C4—C11121.9 (2)C18—C19—H19119.3
C5—C4—C11124.6 (2)O1—C19—H19'117.3
C6—C5—C10119.1 (2)O1'—C19—H19'112.4
C6—C5—C4129.8 (2)C18—C19—H19'117.3
C10—C5—C4111.1 (2)C16—C20—C21130.78 (19)
C7—C6—C5119.0 (3)C16—C20—S2111.48 (16)
C7—C6—H6120.5C21—C20—S2117.72 (15)
C5—C6—H6120.5C20—C21—C22113.64 (18)
C6—C7—C9121.5 (3)C20—C21—H21A108.8
C6—C7—H7119.2C22—C21—H21A108.8
C9—C7—H7119.2C20—C21—H21B108.8
C9—C8—C10118.4 (3)C22—C21—H21B108.8
C9—C8—H8120.8H21A—C21—H21B107.7
C10—C8—H8120.8C23—C22—C21113.0 (2)
C8—C9—C7121.1 (3)C23—C22—H22A109.0
C8—C9—H9119.4C21—C22—H22A109.0
C7—C9—H9119.4C23—C22—H22B109.0
C8—C10—C5120.9 (3)C21—C22—H22B109.0
C8—C10—S1127.5 (3)H22A—C22—H22B107.8
C5—C10—S1111.61 (19)C22—C23—C24112.8 (2)
C15—C11—C4130.17 (19)C22—C23—H23A109.0
C15—C11—C12110.50 (19)C24—C23—H23A109.0
C4—C11—C12118.92 (19)C22—C23—H23B109.0
F2—C12—F1105.7 (2)C24—C23—H23B109.0
F2—C12—C11114.8 (2)H23A—C23—H23B107.8
F1—C12—C11109.4 (2)C23—C24—H24A109.5
F2—C12—C13113.8 (2)C23—C24—H24B109.5
F1—C12—C13108.2 (2)H24A—C24—H24B109.5
C11—C12—C13104.97 (18)C23—C24—H24C109.5
F3—C13—F4107.5 (2)H24A—C24—H24C109.5
F3—C13—C12114.5 (2)H24B—C24—H24C109.5
C1—C2—C3—C4163.3 (6)C11—C12—C13—C14−23.4 (2)
C1'—C2—C3—C4119.3 (14)F3—C13—C14—F6−88.3 (3)
C1—C2—C3—S1−16.7 (7)F4—C13—C14—F631.4 (3)
C1'—C2—C3—S1−60.7 (14)C12—C13—C14—F6146.9 (2)
C10—S1—C3—C40.8 (2)F3—C13—C14—F528.1 (3)
C10—S1—C3—C2−179.3 (3)F4—C13—C14—F5147.89 (19)
C2—C3—C4—C5−179.9 (3)C12—C13—C14—F5−96.7 (2)
S1—C3—C4—C50.1 (3)F3—C13—C14—C15148.0 (2)
C2—C3—C4—C11−3.0 (4)F4—C13—C14—C15−92.2 (2)
S1—C3—C4—C11176.99 (17)C12—C13—C14—C1523.2 (2)
C3—C4—C5—C6−177.8 (3)C4—C11—C15—C164.6 (4)
C11—C4—C5—C65.4 (4)C12—C11—C15—C16177.0 (2)
C3—C4—C5—C10−1.1 (3)C4—C11—C15—C14−172.9 (2)
C11—C4—C5—C10−177.9 (2)C12—C11—C15—C14−0.5 (2)
C10—C5—C6—C7−0.4 (4)F6—C14—C15—C11−137.4 (2)
C4—C5—C6—C7176.1 (3)F5—C14—C15—C11103.4 (2)
C5—C6—C7—C9−0.6 (5)C13—C14—C15—C11−14.7 (2)
C10—C8—C9—C7−1.4 (5)F6—C14—C15—C1644.7 (3)
C6—C7—C9—C81.6 (6)F5—C14—C15—C16−74.5 (2)
C9—C8—C10—C50.3 (4)C13—C14—C15—C16167.42 (19)
C9—C8—C10—S1−177.5 (3)C11—C15—C16—C2047.7 (3)
C6—C5—C10—C80.5 (4)C14—C15—C16—C20−135.0 (2)
C4—C5—C10—C8−176.5 (2)C11—C15—C16—C17−138.3 (2)
C6—C5—C10—S1178.73 (19)C14—C15—C16—C1739.1 (3)
C4—C5—C10—S11.7 (3)C20—C16—C17—C18−0.5 (3)
C3—S1—C10—C8176.7 (3)C15—C16—C17—C18−175.3 (2)
C3—S1—C10—C5−1.4 (2)C16—C17—C18—C19−178.8 (3)
C3—C4—C11—C1568.7 (3)C16—C17—C18—S20.8 (3)
C5—C4—C11—C15−114.7 (3)C20—S2—C18—C17−0.7 (2)
C3—C4—C11—C12−103.1 (3)C20—S2—C18—C19178.9 (3)
C5—C4—C11—C1273.5 (3)C17—C18—C19—O1−156.0 (19)
C15—C11—C12—F2141.2 (2)S2—C18—C19—O125 (2)
C4—C11—C12—F2−45.4 (3)C17—C18—C19—O1'168.9 (15)
C15—C11—C12—F1−100.3 (2)S2—C18—C19—O1'−10.6 (16)
C4—C11—C12—F173.1 (3)C17—C16—C20—C21−178.2 (2)
C15—C11—C12—C1315.6 (3)C15—C16—C20—C21−3.6 (3)
C4—C11—C12—C13−171.1 (2)C17—C16—C20—S2−0.1 (2)
F2—C12—C13—F386.1 (3)C15—C16—C20—S2174.49 (16)
F1—C12—C13—F3−30.9 (3)C18—S2—C20—C160.43 (17)
C11—C12—C13—F3−147.6 (2)C18—S2—C20—C21178.80 (17)
F2—C12—C13—F4−34.0 (3)C16—C20—C21—C22−117.1 (2)
F1—C12—C13—F4−151.1 (2)S2—C20—C21—C2264.9 (2)
C11—C12—C13—F492.2 (2)C20—C21—C22—C23−173.65 (19)
F2—C12—C13—C14−149.7 (2)C21—C22—C23—C24−175.0 (2)
F1—C12—C13—C1493.3 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2080).

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