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

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

doi:10.1107/S1600536808036453

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2311

doi:10.1107/S1600536808036453

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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

Zhen Yang,^a Congbin Fan,^a ^* Min Li,^a Weijun Liu,^a Gang Liu ^a and Seik Weng Ng ^b

^aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: congbinfan@yahoo.com.cn

(Received 23 August 2008; accepted 6 November 2008; online 13 November 2008)

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 ); 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

Crystal data

C₂₄H₂₀F₆OS₂
M_r = 502.52
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.151
S = 1.03
5195 reflections
318 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.25 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

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

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

checkCIF report

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%.

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

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

C₂₄H₂₀F₆OS₂	Z = 2
M_r = 502.52	F(000) = 516
Triclinic, P1	D_x = 1.442 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.051 (1) Å	Cell parameters from 4259 reflections
b = 11.031 (1) Å	θ = 2.5–28.2°
c = 12.019 (1) Å	µ = 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 tube	R_int = 0.019
Graphite monochromator	θ_max = 27.5°, θ_min = 2.5°
ϕ and ω scans	h = −12→13
10086 measured reflections	k = −14→14
5195 independent reflections	l = −15→15

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0768P)² + 0.3784P] where P = (F_o² + 2F_c²)/3
5195 reflections	(Δ/σ)_max = 0.001
318 parameters	Δρ_max = 0.34 e Å⁻³
30 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₄H₂₀F₆OS₂	γ = 103.542 (1)°
M_r = 502.52	V = 1157.5 (2) Å³
Triclinic, P1	Z = 2
a = 10.051 (1) Å	Mo Kα radiation
b = 11.031 (1) Å	µ = 0.29 mm⁻¹
c = 12.019 (1) Å	T = 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 reflections	R_int = 0.019
5195 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	30 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
5195 reflections	Δρ_min = −0.25 e Å⁻³
318 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.43383 (7)	0.52869 (8)	0.19023 (8)	0.0736 (2)
S2	0.86262 (7)	0.60297 (6)	0.65571 (5)	0.05353 (19)
F1	0.89175 (19)	0.80884 (18)	0.17554 (17)	0.0805 (5)
F2	0.8985 (2)	0.6035 (2)	0.06303 (14)	0.0868 (6)
F3	1.16124 (19)	0.8540 (2)	0.22574 (18)	0.0943 (6)
F4	1.1390 (2)	0.6431 (2)	0.19936 (18)	0.0921 (6)
F5	1.10459 (17)	0.92568 (14)	0.44135 (15)	0.0707 (4)
F6	1.19297 (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)
O1	1.010 (3)	0.8304 (18)	0.9249 (10)	0.080 (4)	0.36 (5)
C1	0.5164 (7)	0.8436 (7)	0.3633 (7)	0.104 (3)	0.788 (17)
H1A	0.5476	0.9370	0.4276	0.156*	0.788 (17)
H1B	0.4403	0.7889	0.3812	0.156*	0.788 (17)
H1C	0.4848	0.8435	0.2846	0.156*	0.788 (17)
C1'	0.577 (3)	0.8783 (13)	0.3189 (17)	0.077 (6)	0.212 (17)
H1'A	0.6029	0.9682	0.3880	0.116*	0.212 (17)
H1'B	0.4767	0.8414	0.2910	0.116*	0.212 (17)
H1'C	0.6169	0.8861	0.2522	0.116*	0.212 (17)
C2	0.6323 (4)	0.7854 (3)	0.3580 (3)	0.0885 (10)
H2A	0.6646	0.7900	0.4393	0.106*
H2B	0.7092	0.8446	0.3433	0.106*
C3	0.6050 (3)	0.6395 (3)	0.2628 (2)	0.0565 (6)
C4	0.7027 (2)	0.5769 (2)	0.2221 (2)	0.0454 (5)
C5	0.6422 (3)	0.4353 (2)	0.1294 (2)	0.0519 (6)
C6	0.7084 (3)	0.3380 (3)	0.0696 (2)	0.0677 (7)
H6	0.8061	0.3627	0.0841	0.081*
C7	0.6267 (5)	0.2048 (3)	−0.0111 (3)	0.0914 (11)
H7	0.6703	0.1400	−0.0517	0.110*
C8	0.4127 (4)	0.2581 (4)	0.0223 (3)	0.0846 (10)
H8	0.3149	0.2315	0.0058	0.102*
C9	0.4813 (5)	0.1652 (4)	−0.0332 (3)	0.0991 (13)
H9	0.4292	0.0739	−0.0867	0.119*
C10	0.4937 (3)	0.3945 (3)	0.1048 (2)	0.0615 (7)
C11	0.8549 (2)	0.6521 (2)	0.2655 (2)	0.0424 (5)
C12	0.9296 (3)	0.6987 (3)	0.1805 (2)	0.0560 (6)
C13	1.0846 (3)	0.7499 (3)	0.2438 (2)	0.0576 (6)
C14	1.0847 (2)	0.7868 (2)	0.3798 (2)	0.0480 (5)
C15	0.9421 (2)	0.7024 (2)	0.37843 (19)	0.0387 (4)
C16	0.9193 (2)	0.6924 (2)	0.49357 (19)	0.0385 (4)
C17	0.9764 (2)	0.8081 (2)	0.6132 (2)	0.0467 (5)
H17	1.0247	0.8966	0.6245	0.056*
C18	0.9532 (3)	0.7762 (2)	0.7089 (2)	0.0533 (6)
C19	0.9934 (4)	0.8673 (3)	0.8416 (3)	0.0801 (9)
H19	1.0552	0.9562	0.8702	0.096*	0.64 (5)
H19'	1.0075	0.9613	0.8654	0.096*	0.36 (5)
C20	0.8536 (2)	0.5729 (2)	0.50312 (19)	0.0401 (4)
C21	0.7831 (2)	0.4277 (2)	0.4049 (2)	0.0425 (5)
H21A	0.8296	0.3668	0.4216	0.051*
H21B	0.7949	0.4238	0.3247	0.051*
C22	0.6266 (2)	0.3746 (2)	0.3974 (2)	0.0510 (5)
H22A	0.6139	0.3879	0.4796	0.061*
H22B	0.5782	0.4289	0.3713	0.061*
C23	0.5601 (3)	0.2226 (3)	0.3076 (3)	0.0634 (7)
H23A	0.6027	0.1675	0.3378	0.076*
H23B	0.5800	0.2077	0.2271	0.076*
C24	0.4014 (4)	0.1731 (4)	0.2918 (3)	0.0940 (11)
H24A	0.3648	0.0766	0.2346	0.141*
H24B	0.3583	0.2255	0.2598	0.141*
H24C	0.3810	0.1860	0.3709	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0440 (4)	0.0835 (5)	0.0917 (6)	0.0164 (3)	−0.0006 (3)	0.0430 (4)
S2	0.0674 (4)	0.0499 (3)	0.0462 (3)	0.0127 (3)	0.0157 (3)	0.0262 (3)
F1	0.0839 (11)	0.0906 (12)	0.0950 (12)	0.0251 (9)	0.0131 (9)	0.0717 (11)
F2	0.0934 (13)	0.0972 (13)	0.0451 (9)	−0.0039 (10)	0.0150 (8)	0.0255 (9)
F3	0.0792 (12)	0.1137 (15)	0.0913 (13)	−0.0117 (10)	0.0169 (10)	0.0701 (12)
F4	0.0853 (12)	0.1121 (15)	0.0909 (13)	0.0522 (11)	0.0407 (10)	0.0382 (12)
F5	0.0776 (10)	0.0444 (8)	0.0744 (10)	−0.0017 (7)	0.0125 (8)	0.0233 (7)
F6	0.0408 (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)
O1	0.107 (9)	0.084 (5)	0.053 (4)	0.032 (5)	0.015 (4)	0.033 (3)
C1	0.098 (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)
C2	0.080 (2)	0.0667 (19)	0.102 (2)	0.0363 (16)	0.0055 (18)	0.0168 (18)
C3	0.0474 (13)	0.0579 (14)	0.0639 (15)	0.0171 (11)	0.0035 (11)	0.0285 (12)
C4	0.0462 (12)	0.0475 (12)	0.0416 (11)	0.0112 (9)	0.0022 (9)	0.0226 (10)
C5	0.0569 (14)	0.0512 (13)	0.0419 (12)	0.0071 (10)	0.0020 (10)	0.0228 (10)
C6	0.0835 (19)	0.0575 (15)	0.0530 (15)	0.0147 (14)	0.0191 (14)	0.0182 (12)
C7	0.128 (3)	0.0590 (18)	0.0636 (19)	0.0153 (19)	0.028 (2)	0.0098 (15)
C8	0.077 (2)	0.075 (2)	0.0695 (19)	−0.0144 (17)	−0.0182 (16)	0.0302 (17)
C9	0.126 (3)	0.062 (2)	0.063 (2)	−0.012 (2)	−0.001 (2)	0.0117 (16)
C10	0.0552 (14)	0.0627 (15)	0.0549 (14)	0.0001 (12)	−0.0070 (11)	0.0298 (12)
C11	0.0446 (11)	0.0412 (11)	0.0440 (11)	0.0122 (9)	0.0084 (9)	0.0225 (9)
C12	0.0625 (15)	0.0605 (14)	0.0468 (13)	0.0110 (12)	0.0099 (11)	0.0308 (12)
C13	0.0538 (14)	0.0631 (15)	0.0651 (16)	0.0132 (12)	0.0200 (12)	0.0381 (13)
C14	0.0416 (11)	0.0476 (12)	0.0573 (14)	0.0091 (9)	0.0057 (10)	0.0296 (11)
C15	0.0392 (10)	0.0366 (10)	0.0445 (11)	0.0130 (8)	0.0096 (8)	0.0213 (9)
C16	0.0366 (10)	0.0395 (10)	0.0430 (11)	0.0134 (8)	0.0057 (8)	0.0215 (9)
C17	0.0537 (12)	0.0384 (11)	0.0466 (12)	0.0122 (9)	0.0082 (10)	0.0192 (9)
C18	0.0645 (15)	0.0470 (12)	0.0453 (12)	0.0153 (11)	0.0112 (11)	0.0186 (10)
C19	0.126 (3)	0.0564 (16)	0.0457 (15)	0.0148 (17)	0.0188 (16)	0.0175 (13)
C20	0.0404 (10)	0.0419 (11)	0.0431 (11)	0.0151 (8)	0.0092 (9)	0.0224 (9)
C21	0.0455 (11)	0.0382 (10)	0.0476 (12)	0.0153 (9)	0.0087 (9)	0.0218 (9)
C22	0.0471 (12)	0.0458 (12)	0.0566 (14)	0.0088 (10)	0.0090 (10)	0.0229 (11)
C23	0.0630 (16)	0.0483 (13)	0.0684 (17)	0.0043 (12)	0.0049 (13)	0.0253 (12)
C24	0.073 (2)	0.079 (2)	0.091 (2)	−0.0168 (17)	0.0107 (17)	0.0238 (18)

Geometric parameters (Å, º) top

S1—C10	1.726 (3)	C7—H7	0.9300
S1—C3	1.742 (3)	C8—C9	1.369 (5)
S2—C20	1.717 (2)	C8—C10	1.403 (4)
S2—C18	1.725 (2)	C8—H8	0.9300
F1—C12	1.376 (3)	C9—H9	0.9300
F2—C12	1.331 (3)	C11—C15	1.346 (3)
F3—C13	1.335 (3)	C11—C12	1.512 (3)
F4—C13	1.360 (3)	C12—C13	1.513 (4)
F5—C14	1.366 (3)	C13—C14	1.521 (3)
F6—C14	1.350 (3)	C14—C15	1.510 (3)
O1'—C19	1.236 (5)	C15—C16	1.471 (3)
O1—C19	1.228 (8)	C16—C20	1.385 (3)
C1—C2	1.453 (5)	C16—C17	1.430 (3)
C1—H1A	0.9600	C17—C18	1.358 (3)
C1—H1B	0.9600	C17—H17	0.9300
C1—H1C	0.9600	C18—C19	1.453 (4)
C1'—C2	1.468 (8)	C19—H19	0.9300
C1'—H1'A	0.9600	C19—H19'	0.9300
C1'—H1'B	0.9600	C20—C21	1.497 (3)
C1'—H1'C	0.9600	C21—C22	1.523 (3)
C2—C3	1.499 (4)	C21—H21A	0.9700
C2—H2A	0.9700	C21—H21B	0.9700
C2—H2B	0.9700	C22—C23	1.518 (3)
C3—C4	1.359 (3)	C22—H22A	0.9700
C4—C5	1.441 (3)	C22—H22B	0.9700
C4—C11	1.475 (3)	C23—C24	1.522 (4)
C5—C6	1.399 (4)	C23—H23A	0.9700
C5—C10	1.412 (4)	C23—H23B	0.9700
C6—C7	1.378 (4)	C24—H24A	0.9600
C6—H6	0.9300	C24—H24B	0.9600
C7—C9	1.384 (6)	C24—H24C	0.9600

C10—S1—C3	91.85 (12)	F4—C13—C12	108.6 (2)
C20—S2—C18	92.17 (11)	F3—C13—C14	113.6 (2)
C2—C1—H1A	109.5	F4—C13—C14	108.9 (2)
C2—C1—H1B	109.5	C12—C13—C14	103.50 (19)
H1A—C1—H1B	109.5	F6—C14—F5	105.70 (19)
C2—C1—H1C	109.5	F6—C14—C15	113.35 (17)
H1A—C1—H1C	109.5	F5—C14—C15	111.64 (19)
H1B—C1—H1C	109.5	F6—C14—C13	111.9 (2)
C2—C1'—H1'A	109.5	F5—C14—C13	108.90 (18)
C2—C1'—H1'B	109.5	C15—C14—C13	105.39 (18)
H1'A—C1'—H1'B	109.5	C11—C15—C16	131.72 (19)
C2—C1'—H1'C	109.5	C11—C15—C14	109.62 (18)
H1'A—C1'—H1'C	109.5	C16—C15—C14	118.62 (18)
H1'B—C1'—H1'C	109.5	C20—C16—C17	111.60 (18)
C1—C2—C3	117.8 (3)	C20—C16—C15	126.15 (19)
C1'—C2—C3	117.9 (6)	C17—C16—C15	122.02 (18)
C1—C2—H2A	107.9	C18—C17—C16	113.4 (2)
C1'—C2—H2A	132.3	C18—C17—H17	123.3
C3—C2—H2A	107.9	C16—C17—H17	123.3
C1—C2—H2B	107.9	C17—C18—C19	128.5 (2)
C3—C2—H2B	107.9	C17—C18—S2	111.32 (18)
H2A—C2—H2B	107.2	C19—C18—S2	120.2 (2)
C4—C3—C2	127.0 (2)	O1—C19—C18	125.4 (8)
C4—C3—S1	111.98 (18)	O1'—C19—C18	121.5 (5)
C2—C3—S1	121.0 (2)	O1—C19—H19	107.4
C3—C4—C5	113.4 (2)	O1'—C19—H19	119.3
C3—C4—C11	121.9 (2)	C18—C19—H19	119.3
C5—C4—C11	124.6 (2)	O1—C19—H19'	117.3
C6—C5—C10	119.1 (2)	O1'—C19—H19'	112.4
C6—C5—C4	129.8 (2)	C18—C19—H19'	117.3
C10—C5—C4	111.1 (2)	C16—C20—C21	130.78 (19)
C7—C6—C5	119.0 (3)	C16—C20—S2	111.48 (16)
C7—C6—H6	120.5	C21—C20—S2	117.72 (15)
C5—C6—H6	120.5	C20—C21—C22	113.64 (18)
C6—C7—C9	121.5 (3)	C20—C21—H21A	108.8
C6—C7—H7	119.2	C22—C21—H21A	108.8
C9—C7—H7	119.2	C20—C21—H21B	108.8
C9—C8—C10	118.4 (3)	C22—C21—H21B	108.8
C9—C8—H8	120.8	H21A—C21—H21B	107.7
C10—C8—H8	120.8	C23—C22—C21	113.0 (2)
C8—C9—C7	121.1 (3)	C23—C22—H22A	109.0
C8—C9—H9	119.4	C21—C22—H22A	109.0
C7—C9—H9	119.4	C23—C22—H22B	109.0
C8—C10—C5	120.9 (3)	C21—C22—H22B	109.0
C8—C10—S1	127.5 (3)	H22A—C22—H22B	107.8
C5—C10—S1	111.61 (19)	C22—C23—C24	112.8 (2)
C15—C11—C4	130.17 (19)	C22—C23—H23A	109.0
C15—C11—C12	110.50 (19)	C24—C23—H23A	109.0
C4—C11—C12	118.92 (19)	C22—C23—H23B	109.0
F2—C12—F1	105.7 (2)	C24—C23—H23B	109.0
F2—C12—C11	114.8 (2)	H23A—C23—H23B	107.8
F1—C12—C11	109.4 (2)	C23—C24—H24A	109.5
F2—C12—C13	113.8 (2)	C23—C24—H24B	109.5
F1—C12—C13	108.2 (2)	H24A—C24—H24B	109.5
C11—C12—C13	104.97 (18)	C23—C24—H24C	109.5
F3—C13—F4	107.5 (2)	H24A—C24—H24C	109.5
F3—C13—C12	114.5 (2)	H24B—C24—H24C	109.5

C1—C2—C3—C4	163.3 (6)	C11—C12—C13—C14	−23.4 (2)
C1'—C2—C3—C4	119.3 (14)	F3—C13—C14—F6	−88.3 (3)
C1—C2—C3—S1	−16.7 (7)	F4—C13—C14—F6	31.4 (3)
C1'—C2—C3—S1	−60.7 (14)	C12—C13—C14—F6	146.9 (2)
C10—S1—C3—C4	0.8 (2)	F3—C13—C14—F5	28.1 (3)
C10—S1—C3—C2	−179.3 (3)	F4—C13—C14—F5	147.89 (19)
C2—C3—C4—C5	−179.9 (3)	C12—C13—C14—F5	−96.7 (2)
S1—C3—C4—C5	0.1 (3)	F3—C13—C14—C15	148.0 (2)
C2—C3—C4—C11	−3.0 (4)	F4—C13—C14—C15	−92.2 (2)
S1—C3—C4—C11	176.99 (17)	C12—C13—C14—C15	23.2 (2)
C3—C4—C5—C6	−177.8 (3)	C4—C11—C15—C16	4.6 (4)
C11—C4—C5—C6	5.4 (4)	C12—C11—C15—C16	177.0 (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—C7	176.1 (3)	F5—C14—C15—C11	103.4 (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—C16	44.7 (3)
C6—C7—C9—C8	1.6 (6)	F5—C14—C15—C16	−74.5 (2)
C9—C8—C10—C5	0.3 (4)	C13—C14—C15—C16	167.42 (19)
C9—C8—C10—S1	−177.5 (3)	C11—C15—C16—C20	47.7 (3)
C6—C5—C10—C8	0.5 (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—S1	178.73 (19)	C14—C15—C16—C17	39.1 (3)
C4—C5—C10—S1	1.7 (3)	C20—C16—C17—C18	−0.5 (3)
C3—S1—C10—C8	176.7 (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—C15	68.7 (3)	C16—C17—C18—S2	0.8 (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—C19	178.9 (3)
C5—C4—C11—C12	73.5 (3)	C17—C18—C19—O1	−156.0 (19)
C15—C11—C12—F2	141.2 (2)	S2—C18—C19—O1	25 (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—F1	73.1 (3)	C17—C16—C20—C21	−178.2 (2)
C15—C11—C12—C13	15.6 (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—F3	86.1 (3)	C15—C16—C20—S2	174.49 (16)
F1—C12—C13—F3	−30.9 (3)	C18—S2—C20—C16	0.43 (17)
C11—C12—C13—F3	−147.6 (2)	C18—S2—C20—C21	178.80 (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—C22	64.9 (2)
C11—C12—C13—F4	92.2 (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—C14	93.3 (2)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀F₆OS₂
M_r	502.52
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.051 (1), 11.031 (1), 12.019 (1)
α, β, γ (°)	113.126 (1), 96.882 (1), 103.542 (1)
V (Å³)	1157.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.43 × 0.43 × 0.43

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10086, 5195, 3669
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.151, 1.03
No. of reflections	5195
No. of parameters	318
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.25

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

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

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