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Acta Cryst. (2008). E64, o2311    [ doi:10.1107/S1600536808036453 ]

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

Z. Yang, C. Fan, M. Li, W. Liu, G. Liu and S. W. Ng

Abstract top

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].

Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
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 top
Crystal data top
C24H20F6OS2Z = 2
Mr = 502.52F(000) = 516
Triclinic, P1Dx = 1.442 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.051 (1) ÅCell parameters from 4259 reflections
b = 11.031 (1) Åθ = 2.5–28.2°
c = 12.019 (1) ŵ = 0.29 mm−1
α = 113.126 (1)°T = 296 K
β = 96.882 (1)°Block, colourless
γ = 103.542 (1)°0.43 × 0.43 × 0.43 mm
V = 1157.5 (2) Å3
Data collection top
Bruker SMART area-detector
diffractometer		3669 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
graphiteθmax = 27.5°, θmin = 2.5°
φ and ω scansh = −12→13
10086 measured reflectionsk = −14→14
5195 independent reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0768P)2 + 0.3784P]
where P = (Fo2 + 2Fc2)/3
5195 reflections(Δ/σ)max = 0.001
318 parametersΔρmax = 0.34 e Å−3
30 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C24H20F6OS2γ = 103.542 (1)°
Mr = 502.52V = 1157.5 (2) Å3
Triclinic, P1Z = 2
a = 10.051 (1) ÅMo Kα radiation
b = 11.031 (1) ŵ = 0.29 mm−1
c = 12.019 (1) ÅT = 296 K
α = 113.126 (1)°0.43 × 0.43 × 0.43 mm
β = 96.882 (1)°
Data collection top
Bruker SMART area-detector
diffractometer		3669 reflections with I > 2σ(I)
10086 measured reflectionsRint = 0.019
5195 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.151Δρmax = 0.34 e Å−3
S = 1.03Δρmin = −0.25 e Å−3
5195 reflectionsAbsolute structure: ?
318 parametersFlack parameter: ?
30 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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)
Acknowledgements top

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

references
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