3,3,4,4,5,5-Hexafluoro-1,2-bis­(5-formyl-2-methylsulfanyl-3-thienyl)cyclo­pent-1-ene

Tu, Q.; Fan, C.; Liu, G.; Li, M.; Ng, S.W.

doi:10.1107/S1600536808012695

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1007

doi:10.1107/S1600536808012695

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3,3,4,4,5,5-Hexafluoro-1,2-bis(5-formyl-2-methylsulfanyl-3-thienyl)cyclopent-1-ene

Qidong Tu,^a Congbin Fan,^b Gang Liu,^b ^* Min Li ^b and Seik Weng Ng ^c

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China, ^bJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: liugang0926@yahoo.com.cn

(Received 12 April 2008; accepted 30 April 2008; online 7 May 2008)

In the crystal structure of the title diarylethylene compound, C₁₇H₁₀F₆O₂S₄, the two 3-thienyl substituents are aligned at 44.9 (1) and 40.2 (1)° with respect to the –C—C=C—C– fragment of the central cyclopentenyl ring. The five-membered cyclopentenyl ring adopts an envelope conformation. The flap atom of this ring and the two F atoms bonded to it are disordered over two positions with occupancies 0.810 (5)/0.190 (5).

Related literature

See Liu et al. (2008 ) for background literature on this class of photochromic diarylethene compounds.

Experimental

Crystal data

C₁₇H₁₀F₆O₂S₄
M_r = 488.49
Monoclinic, P 2₁ /c
a = 10.7640 (8) Å
b = 11.8807 (9) Å
c = 15.486 (1) Å
β = 93.407 (1)°
V = 1976.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.55 mm⁻¹
T = 291 (2) K
0.38 × 0.29 × 0.28 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.830, T_max = 0.858
12872 measured reflections
4488 independent reflections
3623 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.03
4488 reflections
292 parameters
32 restraints
H-atom parameters constrained
Δρ_max = 1.28 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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/S1600536808012695/xu2419sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012695/xu2419Isup2.hkl

checkCIF report

Comment top

A previous study describes the structure of a photochromic compound, 1,2-bis[5-(4-cyanophenyl)-2-methyl-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene (Liu et al., 2008). The study is extended to the title compound (Scheme I, Fig. 1). The diarylethylene compound, C₁₇H₁₀F₆O₂S₄, has its 3-thienyl substituents aligned at 41.4 (1) and 43.5 (1)° with respect to the central cyclopentenyl ring, which is almost flat.

Related literature top

See Liu et al. (2008) for background literature on this class of photochromic diarylethene compounds.

Experimental top

5-(Methylthio)thiophene-2-carbaldehyde was brominated to 4-bromo-5-(methylthio)thiophene-2-carbaldehyde at 273 K. The carbonyl group was converted to an acetal group by the treatment of the aldehyde (3.2 g, 13.6 mmol) with glycol (4.2 g, 70 mmol) catalyzed by p-toluenesulfonic acid (0.07 g, 0.41 mmol) in benzene (150 ml). The resulting compound (3.82 g, 13.4 mmol) in THF (50 ml) was reacted with 2.5 M butyllithium (5.34 ml) at 195 K under a nitrogen atmosphere. Octafluorocyclopentene (0.91 ml, 6.68 mmol) was added, and the reaction was quenched by water. Column chromatography on silica gave 3,3,4,4,5,5-hexafluoro- 1,2-bis[5-(1,3-dioxolan-2-yl)-2-methylthio-3-thienyl]cyclopent-1-ene (1.2 g, 2.00 mmol). The compound was hydrolyzed to give the title compound in 90% yield. Yellow crystals were obtained by the vapor diffusion of chloroform and hexane (1:1). C and H elemental analysis, Calc. for C₁₇H₁₀F₆O₂S₄ (%): C 41.80, H 2.06; found: C 41.73, H 2.07%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. Thermal ellipsoid plot (Barbour) at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radii; the minor disorder component is not shown.

3,3,4,4,5,5-Hexafluoro-1,2-bis(5-formyl-2-methylsulfanyl-3-thienyl)cyclopent- 1-ene top

Crystal data top

C₁₇H₁₀F₆O₂S₄	F(000) = 984
M_r = 488.49	D_x = 1.641 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5293 reflections
a = 10.7640 (8) Å	θ = 2.6–28.2°
b = 11.8807 (9) Å	µ = 0.55 mm⁻¹
c = 15.486 (1) Å	T = 291 K
β = 93.407 (1)°	Block, yellow
V = 1976.9 (2) Å³	0.38 × 0.29 × 0.28 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	4488 independent reflections
Radiation source: fine-focus sealed tube	3623 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.830, T_max = 0.858	k = −15→15
12872 measured reflections	l = −20→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0719P)² + 1.6843P] where P = (F_o² + 2F_c²)/3
4488 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 1.28 e Å⁻³
32 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

C₁₇H₁₀F₆O₂S₄	V = 1976.9 (2) Å³
M_r = 488.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7640 (8) Å	µ = 0.55 mm⁻¹
b = 11.8807 (9) Å	T = 291 K
c = 15.486 (1) Å	0.38 × 0.29 × 0.28 mm
β = 93.407 (1)°

Data collection top

Bruker APEXII diffractometer	4488 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3623 reflections with I > 2σ(I)
T_min = 0.830, T_max = 0.858	R_int = 0.017
12872 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	32 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	Δρ_max = 1.28 e Å⁻³
4488 reflections	Δρ_min = −0.70 e Å⁻³
292 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.85945 (7)	0.33347 (7)	0.64145 (5)	0.0517 (2)
S2	0.88965 (7)	−0.05788 (6)	0.39840 (5)	0.0492 (2)
S3	0.71640 (7)	0.12007 (6)	0.59914 (4)	0.0464 (2)
S4	0.91715 (7)	0.19624 (6)	0.38742 (5)	0.04583 (19)
F1	0.56368 (19)	0.45268 (16)	0.37042 (15)	0.0697 (6)
F2	0.4537 (2)	0.3805 (2)	0.46758 (14)	0.0746 (6)
F3	0.3300 (2)	0.3052 (3)	0.3266 (3)	0.0812 (12)	0.810 (5)
F4	0.4907 (3)	0.3241 (2)	0.25152 (15)	0.0715 (10)	0.810 (5)
F5	0.4988 (3)	0.1142 (3)	0.26891 (18)	0.1259 (13)
F6	0.4066 (2)	0.1119 (2)	0.3863 (2)	0.1093 (11)
O1	0.9727 (3)	0.5672 (2)	0.66318 (18)	0.0827 (9)
O2	0.8080 (3)	−0.3083 (2)	0.4030 (3)	0.0962 (10)
C1	0.8505 (3)	0.4474 (2)	0.5720 (2)	0.0494 (7)
C2	0.7748 (3)	0.4263 (2)	0.49994 (19)	0.0442 (6)
H2	0.7594	0.4784	0.4557	0.053*
C3	0.7220 (2)	0.3165 (2)	0.49939 (16)	0.0371 (5)
C4	0.7605 (2)	0.2565 (2)	0.57284 (16)	0.0377 (5)
C5	0.6309 (2)	0.2760 (2)	0.43218 (15)	0.0356 (5)
C6	0.5253 (2)	0.3536 (2)	0.40199 (18)	0.0431 (6)
C7	0.4524 (3)	0.2905 (4)	0.3281 (3)	0.0486 (11)	0.810 (5)
C8	0.4951 (3)	0.1683 (2)	0.3416 (2)	0.0504 (7)
C9	0.6167 (2)	0.1729 (2)	0.39523 (16)	0.0358 (5)
C10	0.6979 (2)	0.0740 (2)	0.39929 (16)	0.0364 (5)
C11	0.8271 (2)	0.0761 (2)	0.39533 (16)	0.0376 (5)
C12	0.7434 (3)	−0.1179 (2)	0.40298 (19)	0.0461 (6)
C13	0.6523 (3)	−0.0383 (2)	0.40251 (17)	0.0420 (6)
H13	0.5682	−0.0557	0.4041	0.050*
C14	0.9139 (3)	0.5520 (3)	0.5951 (2)	0.0642 (9)
H14	0.9091	0.6106	0.5552	0.077*
C15	0.7257 (4)	−0.2395 (3)	0.4026 (2)	0.0620 (9)
H15	0.6444	−0.2661	0.4020	0.074*
C16	0.7725 (3)	0.1094 (3)	0.71059 (18)	0.0535 (7)
H16A	0.8616	0.1157	0.7146	0.080*
H16B	0.7485	0.0380	0.7334	0.080*
H16C	0.7373	0.1689	0.7433	0.080*
C17	1.0583 (3)	0.1414 (3)	0.3464 (2)	0.0593 (8)
H17A	1.1026	0.0985	0.3908	0.089*
H17B	1.1095	0.2026	0.3292	0.089*
H17C	1.0380	0.0939	0.2975	0.089*
F3'	0.3375 (10)	0.2469 (12)	0.4024 (8)	0.081 (4)	0.190 (5)
F4'	0.3867 (17)	0.3304 (12)	0.2800 (9)	0.090 (5)	0.190 (5)
C7'	0.4250 (7)	0.2804 (7)	0.3523 (7)	0.050 (6)	0.190 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0604 (5)	0.0470 (4)	0.0453 (4)	−0.0169 (3)	−0.0169 (3)	−0.0005 (3)
S2	0.0508 (4)	0.0352 (4)	0.0612 (5)	0.0014 (3)	−0.0004 (3)	0.0031 (3)
S3	0.0593 (4)	0.0397 (4)	0.0387 (3)	−0.0147 (3)	−0.0086 (3)	0.0039 (3)
S4	0.0410 (4)	0.0356 (3)	0.0608 (4)	−0.0068 (3)	0.0023 (3)	−0.0021 (3)
F1	0.0693 (12)	0.0492 (10)	0.0876 (14)	−0.0059 (9)	−0.0189 (10)	0.0269 (10)
F2	0.0707 (13)	0.0872 (16)	0.0671 (12)	0.0286 (11)	0.0134 (10)	−0.0040 (11)
F3	0.0335 (13)	0.0724 (19)	0.134 (3)	0.0019 (12)	−0.0234 (15)	−0.0018 (19)
F4	0.086 (2)	0.0789 (18)	0.0469 (13)	−0.0162 (15)	−0.0187 (12)	0.0168 (12)
F5	0.129 (2)	0.140 (2)	0.0991 (19)	0.062 (2)	−0.0753 (17)	−0.0722 (19)
F6	0.0586 (13)	0.0851 (17)	0.180 (3)	−0.0356 (12)	−0.0303 (16)	0.0536 (18)
O1	0.100 (2)	0.0659 (16)	0.0777 (17)	−0.0379 (15)	−0.0308 (15)	−0.0051 (13)
O2	0.102 (2)	0.0389 (13)	0.147 (3)	0.0066 (14)	0.004 (2)	0.0123 (16)
C1	0.0559 (17)	0.0376 (14)	0.0532 (16)	−0.0134 (12)	−0.0079 (13)	−0.0022 (12)
C2	0.0512 (16)	0.0328 (13)	0.0474 (15)	−0.0053 (11)	−0.0067 (12)	0.0013 (11)
C3	0.0411 (13)	0.0315 (12)	0.0381 (12)	−0.0041 (10)	−0.0035 (10)	−0.0036 (10)
C4	0.0403 (13)	0.0349 (12)	0.0375 (12)	−0.0070 (10)	−0.0034 (10)	−0.0034 (10)
C5	0.0357 (12)	0.0345 (12)	0.0361 (12)	−0.0035 (10)	−0.0019 (9)	0.0020 (10)
C6	0.0421 (14)	0.0399 (14)	0.0469 (15)	0.0008 (11)	−0.0008 (11)	0.0027 (11)
C7	0.0330 (18)	0.057 (2)	0.054 (3)	−0.0033 (17)	−0.007 (2)	0.0045 (19)
C8	0.0456 (16)	0.0448 (15)	0.0584 (17)	−0.0084 (12)	−0.0162 (13)	−0.0051 (13)
C9	0.0360 (12)	0.0358 (12)	0.0350 (12)	−0.0067 (10)	−0.0037 (9)	0.0002 (10)
C10	0.0432 (14)	0.0316 (12)	0.0334 (12)	−0.0063 (10)	−0.0047 (10)	−0.0013 (9)
C11	0.0428 (14)	0.0331 (12)	0.0364 (12)	−0.0040 (10)	−0.0038 (10)	−0.0006 (10)
C12	0.0565 (17)	0.0343 (13)	0.0468 (15)	−0.0083 (12)	−0.0022 (12)	0.0022 (11)
C13	0.0467 (15)	0.0362 (13)	0.0424 (14)	−0.0100 (11)	−0.0044 (11)	−0.0010 (11)
C14	0.076 (2)	0.0452 (17)	0.069 (2)	−0.0222 (16)	−0.0169 (17)	−0.0023 (15)
C15	0.080 (2)	0.0343 (15)	0.070 (2)	−0.0059 (15)	−0.0033 (17)	0.0079 (14)
C16	0.0669 (19)	0.0532 (17)	0.0394 (14)	−0.0042 (15)	−0.0055 (13)	0.0047 (13)
C17	0.0416 (16)	0.0531 (18)	0.084 (2)	−0.0022 (13)	0.0075 (15)	0.0001 (16)
F3'	0.048 (5)	0.102 (8)	0.093 (8)	−0.017 (5)	0.007 (5)	−0.019 (6)
F4'	0.083 (9)	0.094 (8)	0.086 (7)	0.014 (7)	−0.043 (7)	0.001 (6)
C7'	0.057 (10)	0.053 (8)	0.038 (8)	−0.001 (7)	−0.002 (7)	0.014 (6)

Geometric parameters (Å, º) top

S1—C4	1.722 (2)	C5—C6	1.516 (4)
S1—C1	1.728 (3)	C6—C7	1.543 (4)
S2—C11	1.728 (3)	C6—C7'	1.554 (8)
S2—C12	1.734 (3)	C7—C8	1.534 (5)
S3—C4	1.744 (3)	C8—C9	1.509 (4)
S3—C16	1.799 (3)	C8—C7'	1.545 (8)
S4—C11	1.734 (3)	C9—C10	1.463 (4)
S4—C17	1.803 (3)	C10—C11	1.397 (4)
F1—C6	1.349 (3)	C10—C13	1.424 (3)
F2—C6	1.349 (3)	C12—C13	1.362 (4)
F3—C7	1.329 (4)	C12—C15	1.456 (4)
F4—C7	1.339 (5)	C13—H13	0.9300
F5—C8	1.298 (4)	C14—H14	0.9300
F6—C8	1.384 (4)	C15—H15	0.9300
O1—C14	1.211 (4)	C16—H16A	0.9600
O2—C15	1.205 (4)	C16—H16B	0.9600
C1—C2	1.364 (4)	C16—H16C	0.9600
C1—C14	1.453 (4)	C17—H17A	0.9600
C2—C3	1.423 (3)	C17—H17B	0.9600
C2—H2	0.9300	C17—H17C	0.9600
C3—C4	1.385 (4)	F3'—C7'	1.317 (8)
C3—C5	1.468 (3)	F4'—C7'	1.313 (8)
C5—C9	1.356 (3)

C4—S1—C1	91.26 (13)	F6—C8—C7'	90.5 (5)
C11—S2—C12	91.55 (13)	C9—C8—C7'	108.8 (3)
C4—S3—C16	102.05 (14)	C5—C9—C10	130.9 (2)
C11—S4—C17	102.34 (14)	C5—C9—C8	109.7 (2)
C2—C1—C14	127.4 (3)	C10—C9—C8	119.3 (2)
C2—C1—S1	112.0 (2)	C11—C10—C13	111.4 (2)
C14—C1—S1	120.6 (2)	C11—C10—C9	125.3 (2)
C1—C2—C3	113.1 (2)	C13—C10—C9	123.3 (2)
C1—C2—H2	123.5	C10—C11—S2	111.69 (19)
C3—C2—H2	123.5	C10—C11—S4	125.5 (2)
C4—C3—C2	111.5 (2)	S2—C11—S4	122.82 (16)
C4—C3—C5	124.7 (2)	C13—C12—C15	126.5 (3)
C2—C3—C5	123.7 (2)	C13—C12—S2	111.7 (2)
C3—C4—S1	112.20 (19)	C15—C12—S2	121.8 (3)
C3—C4—S3	126.69 (19)	C12—C13—C10	113.7 (2)
S1—C4—S3	121.10 (15)	C12—C13—H13	123.2
C9—C5—C3	130.4 (2)	C10—C13—H13	123.2
C9—C5—C6	110.8 (2)	O1—C14—C1	123.8 (3)
C3—C5—C6	118.5 (2)	O1—C14—H14	118.1
F1—C6—F2	105.5 (2)	C1—C14—H14	118.1
F1—C6—C5	113.7 (2)	O2—C15—C12	125.2 (4)
F2—C6—C5	111.3 (2)	O2—C15—H15	117.4
F1—C6—C7	107.9 (3)	C12—C15—H15	117.4
F2—C6—C7	112.7 (3)	S3—C16—H16A	109.5
C5—C6—C7	105.8 (2)	S3—C16—H16B	109.5
F1—C6—C7'	121.9 (4)	H16A—C16—H16B	109.5
F2—C6—C7'	95.4 (4)	S3—C16—H16C	109.5
C5—C6—C7'	107.4 (3)	H16A—C16—H16C	109.5
F3—C7—F4	107.7 (3)	H16B—C16—H16C	109.5
F3—C7—C8	114.6 (3)	S4—C17—H17A	109.5
F4—C7—C8	107.3 (3)	S4—C17—H17B	109.5
F3—C7—C6	114.1 (4)	H17A—C17—H17B	109.5
F4—C7—C6	110.1 (3)	S4—C17—H17C	109.5
C8—C7—C6	102.9 (2)	H17A—C17—H17C	109.5
F5—C8—F6	104.6 (3)	H17B—C17—H17C	109.5
F5—C8—C9	115.2 (3)	F4'—C7'—F3'	116.1 (12)
F6—C8—C9	110.0 (2)	F4'—C7'—C8	115.4 (10)
F5—C8—C7	112.0 (3)	F3'—C7'—C8	100.0 (8)
F6—C8—C7	108.5 (3)	F4'—C7'—C6	110.0 (9)
C9—C8—C7	106.5 (2)	F3'—C7'—C6	112.1 (8)
F5—C8—C7'	124.0 (4)	C8—C7'—C6	101.9 (4)

C4—S1—C1—C2	0.1 (3)	F5—C8—C9—C5	140.8 (3)
C4—S1—C1—C14	177.1 (3)	F6—C8—C9—C5	−101.3 (3)
C14—C1—C2—C3	−176.8 (3)	C7—C8—C9—C5	16.0 (4)
S1—C1—C2—C3	0.0 (4)	C7'—C8—C9—C5	−3.7 (5)
C1—C2—C3—C4	−0.1 (4)	F5—C8—C9—C10	−38.5 (4)
C1—C2—C3—C5	175.6 (3)	F6—C8—C9—C10	79.4 (3)
C2—C3—C4—S1	0.1 (3)	C7—C8—C9—C10	−163.3 (3)
C5—C3—C4—S1	−175.5 (2)	C7'—C8—C9—C10	177.0 (5)
C2—C3—C4—S3	178.9 (2)	C5—C9—C10—C11	−41.3 (4)
C5—C3—C4—S3	3.2 (4)	C8—C9—C10—C11	137.8 (3)
C1—S1—C4—C3	−0.1 (2)	C5—C9—C10—C13	142.7 (3)
C1—S1—C4—S3	−178.93 (19)	C8—C9—C10—C13	−38.2 (4)
C16—S3—C4—C3	−167.9 (3)	C13—C10—C11—S2	−1.5 (3)
C16—S3—C4—S1	10.8 (2)	C9—C10—C11—S2	−177.9 (2)
C4—C3—C5—C9	−41.9 (4)	C13—C10—C11—S4	178.00 (19)
C2—C3—C5—C9	142.9 (3)	C9—C10—C11—S4	1.6 (4)
C4—C3—C5—C6	131.4 (3)	C12—S2—C11—C10	1.0 (2)
C2—C3—C5—C6	−43.8 (4)	C12—S2—C11—S4	−178.51 (18)
C9—C5—C6—F1	−127.5 (3)	C17—S4—C11—C10	−160.0 (2)
C3—C5—C6—F1	58.0 (3)	C17—S4—C11—S2	19.5 (2)
C9—C5—C6—F2	113.5 (3)	C11—S2—C12—C13	−0.3 (2)
C3—C5—C6—F2	−61.0 (3)	C11—S2—C12—C15	176.7 (3)
C9—C5—C6—C7	−9.2 (3)	C15—C12—C13—C10	−177.4 (3)
C3—C5—C6—C7	176.3 (3)	S2—C12—C13—C10	−0.6 (3)
C9—C5—C6—C7'	10.3 (5)	C11—C10—C13—C12	1.4 (3)
C3—C5—C6—C7'	−164.2 (5)	C9—C10—C13—C12	177.8 (2)
F1—C6—C7—F3	−95.2 (4)	C2—C1—C14—O1	174.5 (4)
F2—C6—C7—F3	20.9 (5)	S1—C1—C14—O1	−2.0 (6)
C5—C6—C7—F3	142.8 (3)	C13—C12—C15—O2	180.0 (4)
C7'—C6—C7—F3	45.2 (10)	S2—C12—C15—O2	3.4 (5)
F1—C6—C7—F4	25.9 (4)	F5—C8—C7'—F4'	−12.0 (12)
F2—C6—C7—F4	142.0 (3)	F6—C8—C7'—F4'	−120.0 (10)
C5—C6—C7—F4	−96.1 (3)	C9—C8—C7'—F4'	128.6 (10)
C7'—C6—C7—F4	166.3 (11)	C7—C8—C7'—F4'	42.7 (11)
F1—C6—C7—C8	140.1 (3)	F5—C8—C7'—F3'	113.4 (7)
F2—C6—C7—C8	−103.8 (3)	F6—C8—C7'—F3'	5.4 (7)
C5—C6—C7—C8	18.0 (3)	C9—C8—C7'—F3'	−106.0 (7)
C7'—C6—C7—C8	−79.5 (10)	C7—C8—C7'—F3'	168.0 (14)
F3—C7—C8—F5	88.4 (5)	F5—C8—C7'—C6	−131.2 (5)
F4—C7—C8—F5	−31.1 (4)	F6—C8—C7'—C6	120.7 (5)
C6—C7—C8—F5	−147.2 (3)	C9—C8—C7'—C6	9.3 (7)
F3—C7—C8—F6	−26.5 (5)	C7—C8—C7'—C6	−76.6 (10)
F4—C7—C8—F6	−146.0 (3)	F1—C6—C7'—F4'	−0.8 (12)
C6—C7—C8—F6	97.9 (3)	F2—C6—C7'—F4'	111.2 (10)
F3—C7—C8—C9	−144.9 (4)	C5—C6—C7'—F4'	−134.5 (10)
F4—C7—C8—C9	95.6 (3)	C7—C6—C7'—F4'	−46.4 (12)
C6—C7—C8—C9	−20.5 (4)	F1—C6—C7'—F3'	−131.7 (8)
F3—C7—C8—C7'	−44.8 (10)	F2—C6—C7'—F3'	−19.7 (9)
F4—C7—C8—C7'	−164.3 (11)	C5—C6—C7'—F3'	94.7 (9)
C6—C7—C8—C7'	79.6 (10)	C7—C6—C7'—F3'	−177.3 (15)
C3—C5—C9—C10	−11.3 (5)	F1—C6—C7'—C8	122.1 (5)
C6—C5—C9—C10	175.0 (3)	F2—C6—C7'—C8	−125.8 (5)
C3—C5—C9—C8	169.5 (3)	C5—C6—C7'—C8	−11.5 (7)
C6—C5—C9—C8	−4.2 (3)	C7—C6—C7'—C8	76.6 (10)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀F₆O₂S₄
M_r	488.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	10.7640 (8), 11.8807 (9), 15.486 (1)
β (°)	93.407 (1)
V (Å³)	1976.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.38 × 0.29 × 0.28

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.830, 0.858
No. of measured, independent and observed [I > 2σ(I)] reflections	12872, 4488, 3623
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.03
No. of reflections	4488
No. of parameters	292
No. of restraints	32
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.28, −0.70

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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, China (grant Nos. 0620012 and 050017), the Science Funds of the Education Office of Jiangxi, China (grant Nos. [2005]140 and [2007]279), and the Research Fund of Jiangxi Science and Technology Normal University, China.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, G., Tu, Q., Zhang, Q., Fan, C. & Yang, T. (2008). Acta Cryst. E64, o938. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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