1-[5-(3-Chloro­phen­yl)-2-methyl-3-thi­en­yl]-3,3,4,4,5,5-hexa­fluoro-2-(2-methoxy­phen­yl)­cyclo­pent-1-ene

Fan, C.; Liu, W.; Liu, G.; Yang, T.

doi:10.1107/S1600536809013993

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1105

doi:10.1107/S1600536809013993

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1-[5-(3-Chlorophenyl)-2-methyl-3-thienyl]-3,3,4,4,5,5-hexafluoro-2-(2-methoxyphenyl)cyclopent-1-ene

Congbin Fan,^a ^* Weijun Liu,^a Gang Liu ^a and Tianshe Yang ^a

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

(Received 11 April 2009; accepted 14 April 2009; online 25 April 2009)

The title compound, C₂₃H₁₅ClF₆OS, has thienyl and phenylene substituents on the double-bond C atoms of the envelope-shaped cyclopentenyl ring. The aromatic systems are aligned at 55.3 (4) (thienyl) and 60.8 (7)° (phenylene) with respect to the planar C—C=C—C portion of the main central cyclopentenyl ring.

Related literature

For the synthesis of the precursors and related compounds, see: Fan et al. (2008 , 2009 ); Pu et al. (2008 ).

Experimental

Crystal data

C₂₃H₁₅ClF₆OS
M_r = 488.86
Triclinic, $[P \overline 1]$
a = 9.4057 (10) Å
b = 10.2900 (11) Å
c = 11.9548 (13) Å
α = 83.529 (1)°
β = 71.564 (1)°
γ = 80.639 (1)°
V = 1080.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 291 K
0.49 × 0.45 × 0.33 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.851, T_max = 0.896
8254 measured reflections
3997 independent reflections
3358 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.111
S = 1.03
3997 reflections
321 parameters
553 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.36 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: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013993/ng2571sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013993/ng2571Isup2.hkl

checkCIF report

Comment top

Crystal of the compound when dissolved in hexane can show photochromism. Upon irradiation with 365 nm light, the colorless crystals hexane solution turns blue rapidly. The blue compound displays an absorption maximum at 584 nm. Upon irradiation with visible light with a wavelength greater than 510 nm, the blue crystals hexane solution revert to their initial colorless state; a hexane solution has an absorption maximum at 291 nm. In a polymethylmethacylate amorphous film, the title diarylethene also demonstrates photochromism as similar as that in hexane.

Related literature top

For the synthesis of the precursors and related compounds, see: Fan et al. (2008, 2009); Pu et al. (2008).

Experimental top

The title compound was synthesized from the reaction of (2-methoxylpheny)perfluorocyclopent-1-ene (1.43 g, 4.75 mmol) (Fan et al., 2009) and 3-bromo-2-methyl-5-(3-chlorophenyl)thiophene (1.44 g, 5 mmol) (Fan et al., 2008) with n-butyllithium (2.0 ml, 5 mmol) at 195 K under a nitrogen atmosphere. After an hour, the reaction was quenced by the addition of water. The solid product was purified by column chromatography on silica with petroleum ether as the eluent to give the title compound 1.58 g (3.23 mmol) in 68% yield. C&H elemental analysis. Calc. for C₂₃H₁₅ClF₆OS: C 56.51, H, 3.09%. Found C 55.92, H 3.15%.

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: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. The diorder in cyclopent-1-ene ring.

1-[5-(3-Chlorophenyl)-2-methyl-3-thienyl]-3,3,4,4,5,5- hexafluoro-2-(2-methoxyphenyl)cyclopent-1-ene top

Crystal data top

C₂₃H₁₅ClF₆OS	Z = 2
M_r = 488.86	F(000) = 496
Triclinic, P1	D_x = 1.502 Mg m⁻³
a = 9.4057 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2900 (11) Å	Cell parameters from 4346 reflections
c = 11.9548 (13) Å	θ = 2.5–28.1°
α = 83.529 (1)°	µ = 0.34 mm⁻¹
β = 71.564 (1)°	T = 291 K
γ = 80.639 (1)°	Block, colourless
V = 1080.7 (2) Å³	0.49 × 0.45 × 0.33 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3997 independent reflections
Radiation source: fine-focus sealed tube	3358 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.851, T_max = 0.896	k = −12→12
8254 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0497P)² + 0.4496P] where P = (F_o² + 2F_c²)/3
3997 reflections	(Δ/σ)_max = 0.001
321 parameters	Δρ_max = 0.28 e Å⁻³
553 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₃H₁₅ClF₆OS	γ = 80.639 (1)°
M_r = 488.86	V = 1080.7 (2) Å³
Triclinic, P1	Z = 2
a = 9.4057 (10) Å	Mo Kα radiation
b = 10.2900 (11) Å	µ = 0.34 mm⁻¹
c = 11.9548 (13) Å	T = 291 K
α = 83.529 (1)°	0.49 × 0.45 × 0.33 mm
β = 71.564 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3997 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3358 reflections with I > 2σ(I)
T_min = 0.851, T_max = 0.896	R_int = 0.011
8254 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	553 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
3997 reflections	Δρ_min = −0.36 e Å⁻³
321 parameters

Special details top

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 of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C9	0.7086 (3)	0.7630 (3)	0.5031 (3)	0.0560 (8)	0.784 (3)
F1	0.5898 (3)	0.8609 (2)	0.5303 (2)	0.0930 (9)	0.784 (3)
F2	0.7750 (3)	0.7584 (2)	0.58991 (15)	0.0854 (7)	0.784 (3)
C9'	0.6784 (10)	0.7854 (12)	0.4846 (8)	0.0560 (8)	0.216 (3)
F1'	0.5498 (9)	0.8402 (8)	0.4640 (8)	0.0930 (9)	0.216 (3)
F2'	0.6890 (12)	0.8415 (10)	0.5755 (6)	0.0854 (7)	0.216 (3)
C10	0.6576 (3)	0.6302 (3)	0.5013 (3)	0.0566 (7)	0.826 (2)
F3	0.52853 (19)	0.6483 (2)	0.4715 (2)	0.0893 (6)	0.826 (2)
F4	0.6283 (3)	0.56317 (19)	0.60649 (15)	0.0877 (6)	0.826 (2)
C10'	0.6811 (14)	0.6391 (15)	0.5180 (12)	0.0566 (7)	0.174 (2)
F3'	0.5428 (9)	0.6053 (11)	0.5606 (12)	0.0893 (6)	0.174 (2)
F4'	0.7538 (10)	0.5982 (9)	0.5974 (7)	0.0877 (6)	0.174 (2)
C11	0.7876 (3)	0.5608 (3)	0.4040 (3)	0.0504 (6)	0.834 (5)
F5	0.7345 (3)	0.4861 (3)	0.34450 (17)	0.0778 (7)	0.834 (5)
F6	0.8815 (3)	0.4760 (2)	0.4529 (2)	0.0771 (7)	0.834 (5)
C11'	0.7621 (15)	0.5759 (12)	0.4012 (12)	0.0504 (6)	0.166 (5)
F5'	0.6680 (14)	0.5518 (13)	0.3457 (9)	0.0778 (7)	0.166 (5)
F6'	0.8458 (15)	0.4630 (13)	0.4176 (13)	0.0771 (7)	0.166 (5)
Cl1	1.52883 (10)	0.09741 (8)	0.13406 (7)	0.1001 (3)
S1	1.10823 (7)	0.64743 (6)	−0.01005 (5)	0.05725 (18)
O1	1.11475 (18)	0.81945 (15)	0.35023 (17)	0.0710 (5)
C1	1.0232 (2)	0.9304 (2)	0.32810 (19)	0.0521 (5)
C2	1.0714 (3)	1.0534 (2)	0.2928 (2)	0.0672 (6)
H2	1.1715	1.0634	0.2819	0.081*
C3	0.9705 (3)	1.1608 (2)	0.2740 (2)	0.0705 (7)
H3	1.0039	1.2427	0.2500	0.085*
C4	0.8232 (3)	1.1490 (2)	0.2899 (2)	0.0650 (6)
H4	0.7562	1.2222	0.2777	0.078*
C5	0.7744 (3)	1.0270 (2)	0.32442 (19)	0.0539 (5)
H5	0.6738	1.0188	0.3356	0.065*
C6	0.8730 (2)	0.91614 (18)	0.34282 (16)	0.0444 (4)
C7	1.2362 (3)	0.8347 (3)	0.3900 (2)	0.0758 (7)
H7A	1.3143	0.8689	0.3256	0.114*
H7B	1.2755	0.7506	0.4198	0.114*
H7C	1.2017	0.8949	0.4518	0.114*
C8	0.8185 (2)	0.78631 (19)	0.38147 (17)	0.0442 (4)
C12	0.8636 (2)	0.67244 (18)	0.32766 (16)	0.0413 (4)
C13	0.9725 (2)	0.64498 (17)	0.21130 (16)	0.0419 (4)
C14	1.0915 (2)	0.53693 (18)	0.19382 (17)	0.0440 (4)
H14	1.1096	0.4798	0.2554	0.053*
C15	1.1763 (2)	0.52489 (19)	0.07887 (17)	0.0461 (4)
C16	0.9669 (2)	0.71461 (19)	0.10727 (18)	0.0488 (5)
C17	0.8561 (3)	0.8294 (2)	0.0852 (2)	0.0666 (6)
H17A	0.7603	0.8263	0.1451	0.100*
H17B	0.8439	0.8248	0.0090	0.100*
H17C	0.8932	0.9104	0.0873	0.100*
C18	1.3086 (2)	0.4285 (2)	0.02687 (17)	0.0480 (4)
C19	1.3943 (3)	0.4423 (2)	−0.0917 (2)	0.0658 (6)
H19	1.3666	0.5128	−0.1399	0.079*
C20	1.5198 (3)	0.3523 (3)	−0.1381 (2)	0.0772 (7)
H20	1.5763	0.3638	−0.2170	0.093*
C21	1.5622 (3)	0.2472 (3)	−0.0706 (2)	0.0681 (6)
H21	1.6467	0.1868	−0.1025	0.082*
C22	1.4773 (3)	0.2320 (2)	0.0462 (2)	0.0594 (5)
C23	1.3525 (2)	0.3205 (2)	0.09609 (19)	0.0531 (5)
H23	1.2977	0.3084	0.1754	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C9	0.0574 (15)	0.0530 (16)	0.0522 (14)	−0.0082 (12)	−0.0075 (11)	−0.0065 (12)
F1	0.0854 (14)	0.0621 (11)	0.0886 (17)	0.0065 (10)	0.0275 (13)	−0.0103 (11)
F2	0.1147 (17)	0.1028 (17)	0.0470 (9)	−0.0445 (13)	−0.0213 (10)	−0.0054 (10)
C9'	0.0574 (15)	0.0530 (16)	0.0522 (14)	−0.0082 (12)	−0.0075 (11)	−0.0065 (12)
F1'	0.0854 (14)	0.0621 (11)	0.0886 (17)	0.0065 (10)	0.0275 (13)	−0.0103 (11)
F2'	0.1147 (17)	0.1028 (17)	0.0470 (9)	−0.0445 (13)	−0.0213 (10)	−0.0054 (10)
C10	0.0539 (14)	0.0575 (13)	0.0548 (14)	−0.0176 (11)	−0.0095 (10)	0.0055 (11)
F3	0.0540 (9)	0.0936 (14)	0.1218 (17)	−0.0148 (9)	−0.0273 (11)	−0.0044 (12)
F4	0.1098 (16)	0.0752 (11)	0.0590 (10)	−0.0282 (11)	0.0021 (10)	0.0153 (8)
C10'	0.0539 (14)	0.0575 (13)	0.0548 (14)	−0.0176 (11)	−0.0095 (10)	0.0055 (11)
F3'	0.0540 (9)	0.0936 (14)	0.1218 (17)	−0.0148 (9)	−0.0273 (11)	−0.0044 (12)
F4'	0.1098 (16)	0.0752 (11)	0.0590 (10)	−0.0282 (11)	0.0021 (10)	0.0153 (8)
C11	0.0549 (14)	0.0419 (12)	0.0553 (11)	−0.0108 (11)	−0.0182 (10)	0.0030 (9)
F5	0.0961 (16)	0.0636 (15)	0.0790 (10)	−0.0429 (13)	−0.0152 (10)	−0.0131 (10)
F6	0.0748 (13)	0.0608 (10)	0.0836 (16)	0.0013 (9)	−0.0233 (9)	0.0277 (10)
C11'	0.0549 (14)	0.0419 (12)	0.0553 (11)	−0.0108 (11)	−0.0182 (10)	0.0030 (9)
F5'	0.0961 (16)	0.0636 (15)	0.0790 (10)	−0.0429 (13)	−0.0152 (10)	−0.0131 (10)
F6'	0.0748 (13)	0.0608 (10)	0.0836 (16)	0.0013 (9)	−0.0233 (9)	0.0277 (10)
Cl1	0.0996 (6)	0.0937 (5)	0.0895 (5)	0.0389 (4)	−0.0325 (4)	0.0023 (4)
S1	0.0699 (4)	0.0557 (3)	0.0415 (3)	0.0014 (3)	−0.0171 (2)	0.0026 (2)
O1	0.0581 (9)	0.0508 (9)	0.1132 (14)	−0.0043 (7)	−0.0380 (9)	−0.0118 (9)
C1	0.0571 (12)	0.0424 (10)	0.0589 (12)	−0.0093 (9)	−0.0176 (10)	−0.0084 (9)
C2	0.0677 (14)	0.0549 (13)	0.0837 (16)	−0.0232 (11)	−0.0220 (12)	−0.0052 (12)
C3	0.0964 (19)	0.0432 (12)	0.0748 (16)	−0.0224 (12)	−0.0259 (14)	0.0020 (11)
C4	0.0873 (17)	0.0440 (12)	0.0642 (14)	−0.0038 (11)	−0.0281 (12)	0.0024 (10)
C5	0.0603 (12)	0.0479 (11)	0.0533 (12)	−0.0045 (9)	−0.0188 (10)	−0.0024 (9)
C6	0.0521 (11)	0.0388 (10)	0.0421 (10)	−0.0067 (8)	−0.0127 (8)	−0.0059 (8)
C7	0.0712 (16)	0.0849 (18)	0.0764 (17)	−0.0021 (14)	−0.0305 (13)	−0.0147 (14)
C8	0.0458 (10)	0.0430 (10)	0.0450 (10)	−0.0086 (8)	−0.0144 (8)	−0.0029 (8)
C12	0.0436 (10)	0.0388 (9)	0.0451 (10)	−0.0074 (8)	−0.0181 (8)	−0.0002 (8)
C13	0.0484 (10)	0.0366 (9)	0.0436 (10)	−0.0088 (8)	−0.0171 (8)	−0.0016 (7)
C14	0.0510 (11)	0.0389 (9)	0.0429 (10)	−0.0050 (8)	−0.0171 (8)	0.0006 (8)
C15	0.0516 (11)	0.0424 (10)	0.0457 (10)	−0.0070 (8)	−0.0169 (9)	−0.0019 (8)
C16	0.0577 (12)	0.0431 (10)	0.0471 (11)	−0.0033 (9)	−0.0203 (9)	−0.0015 (8)
C17	0.0837 (17)	0.0573 (13)	0.0593 (13)	0.0119 (12)	−0.0337 (12)	−0.0014 (11)
C18	0.0510 (11)	0.0471 (11)	0.0461 (10)	−0.0060 (8)	−0.0142 (9)	−0.0067 (8)
C19	0.0787 (16)	0.0590 (13)	0.0490 (12)	−0.0009 (11)	−0.0087 (11)	−0.0029 (10)
C20	0.0825 (17)	0.0754 (17)	0.0548 (14)	−0.0005 (14)	0.0032 (12)	−0.0114 (12)
C21	0.0601 (14)	0.0703 (15)	0.0658 (15)	0.0051 (11)	−0.0086 (11)	−0.0218 (12)
C22	0.0572 (13)	0.0586 (13)	0.0627 (13)	0.0036 (10)	−0.0226 (11)	−0.0089 (10)
C23	0.0513 (11)	0.0568 (12)	0.0477 (11)	−0.0030 (9)	−0.0115 (9)	−0.0058 (9)

Geometric parameters (Å, º) top

C9—F1	1.359 (3)	C3—H3	0.9300
C9—F2	1.363 (4)	C4—C5	1.381 (3)
C9—C8	1.514 (3)	C4—H4	0.9300
C9—C10	1.525 (4)	C5—C6	1.392 (3)
C9'—F2'	1.324 (9)	C5—H5	0.9300
C9'—F1'	1.332 (9)	C6—C8	1.481 (3)
C9'—C8	1.493 (8)	C7—H7A	0.9600
C9'—C10'	1.512 (9)	C7—H7B	0.9600
C10—F4	1.334 (3)	C7—H7C	0.9600
C10—F3	1.349 (3)	C8—C12	1.342 (3)
C10—C11	1.536 (4)	C12—C13	1.469 (3)
C10'—F3'	1.327 (10)	C13—C16	1.375 (3)
C10'—F4'	1.332 (10)	C13—C14	1.426 (3)
C10'—C11'	1.524 (9)	C14—C15	1.361 (3)
C11—F5	1.348 (3)	C14—H14	0.9300
C11—F6	1.358 (3)	C15—C18	1.472 (3)
C11—C12	1.510 (3)	C16—C17	1.502 (3)
C11'—F6'	1.326 (10)	C17—H17A	0.9600
C11'—F5'	1.328 (10)	C17—H17B	0.9600
C11'—C12	1.500 (9)	C17—H17C	0.9600
Cl1—C22	1.741 (2)	C18—C19	1.396 (3)
S1—C16	1.718 (2)	C18—C23	1.396 (3)
S1—C15	1.731 (2)	C19—C20	1.380 (3)
O1—C1	1.368 (3)	C19—H19	0.9300
O1—C7	1.405 (3)	C20—C21	1.359 (4)
C1—C2	1.389 (3)	C20—H20	0.9300
C1—C6	1.398 (3)	C21—C22	1.377 (3)
C2—C3	1.383 (4)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.376 (3)
C3—C4	1.361 (4)	C23—H23	0.9300

F1—C9—F2	105.1 (3)	C5—C6—C8	120.66 (18)
F1—C9—C8	112.8 (2)	C1—C6—C8	120.53 (17)
F2—C9—C8	111.9 (2)	O1—C7—H7A	109.5
F1—C9—C10	111.9 (3)	O1—C7—H7B	109.5
F2—C9—C10	110.1 (2)	H7A—C7—H7B	109.5
C8—C9—C10	105.2 (2)	O1—C7—H7C	109.5
F2'—C9'—F1'	107.7 (8)	H7A—C7—H7C	109.5
F2'—C9'—C8	112.1 (8)	H7B—C7—H7C	109.5
F1'—C9'—C8	116.1 (8)	C12—C8—C6	129.26 (18)
F2'—C9'—C10'	107.2 (10)	C12—C8—C9'	114.1 (5)
F1'—C9'—C10'	112.4 (9)	C6—C8—C9'	115.9 (5)
C8—C9'—C10'	100.9 (7)	C12—C8—C9	109.6 (2)
F4—C10—F3	106.5 (2)	C6—C8—C9	120.8 (2)
F4—C10—C9	112.6 (3)	C8—C12—C13	129.51 (17)
F3—C10—C9	110.1 (3)	C8—C12—C11'	106.6 (6)
F4—C10—C11	114.1 (3)	C13—C12—C11'	123.3 (6)
F3—C10—C11	110.1 (2)	C8—C12—C11	111.5 (2)
C9—C10—C11	103.5 (2)	C13—C12—C11	118.97 (19)
F3'—C10'—F4'	108.1 (9)	C16—C13—C14	112.60 (17)
F3'—C10'—C9'	111.9 (11)	C16—C13—C12	124.45 (17)
F4'—C10'—C9'	112.7 (11)	C14—C13—C12	122.85 (16)
F3'—C10'—C11'	109.3 (11)	C15—C14—C13	113.91 (17)
F4'—C10'—C11'	111.1 (11)	C15—C14—H14	123.0
C9'—C10'—C11'	103.7 (9)	C13—C14—H14	123.0
F5—C11—F6	105.7 (2)	C14—C15—C18	129.71 (18)
F5—C11—C12	113.2 (2)	C14—C15—S1	109.86 (15)
F6—C11—C12	112.9 (2)	C18—C15—S1	120.42 (15)
F5—C11—C10	110.8 (2)	C13—C16—C17	129.94 (19)
F6—C11—C10	110.0 (3)	C13—C16—S1	110.41 (15)
C12—C11—C10	104.2 (2)	C17—C16—S1	119.58 (16)
F6'—C11'—F5'	107.9 (9)	C16—C17—H17A	109.5
F6'—C11'—C12	109.1 (11)	C16—C17—H17B	109.5
F5'—C11'—C12	110.4 (9)	H17A—C17—H17B	109.5
F6'—C11'—C10'	110.9 (12)	C16—C17—H17C	109.5
F5'—C11'—C10'	113.1 (11)	H17A—C17—H17C	109.5
C12—C11'—C10'	105.4 (8)	H17B—C17—H17C	109.5
C16—S1—C15	93.21 (9)	C19—C18—C23	118.1 (2)
C1—O1—C7	118.22 (18)	C19—C18—C15	121.50 (19)
O1—C1—C2	123.8 (2)	C23—C18—C15	120.39 (18)
O1—C1—C6	116.66 (17)	C20—C19—C18	120.6 (2)
C2—C1—C6	119.5 (2)	C20—C19—H19	119.7
C3—C2—C1	120.0 (2)	C18—C19—H19	119.7
C3—C2—H2	120.0	C21—C20—C19	121.2 (2)
C1—C2—H2	120.0	C21—C20—H20	119.4
C4—C3—C2	121.2 (2)	C19—C20—H20	119.4
C4—C3—H3	119.4	C20—C21—C22	118.6 (2)
C2—C3—H3	119.4	C20—C21—H21	120.7
C3—C4—C5	119.2 (2)	C22—C21—H21	120.7
C3—C4—H4	120.4	C23—C22—C21	122.0 (2)
C5—C4—H4	120.4	C23—C22—Cl1	118.70 (18)
C4—C5—C6	121.3 (2)	C21—C22—Cl1	119.34 (18)
C4—C5—H5	119.4	C22—C23—C18	119.6 (2)
C6—C5—H5	119.4	C22—C23—H23	120.2
C5—C6—C1	118.77 (18)	C18—C23—H23	120.2

F1—C9—C10—F4	−89.8 (3)	C10—C9—C8—C12	−16.4 (3)
F2—C9—C10—F4	26.7 (4)	F1—C9—C8—C6	47.6 (4)
C8—C9—C10—F4	147.5 (3)	F2—C9—C8—C6	−70.7 (3)
F1—C9—C10—F3	28.9 (4)	C10—C9—C8—C6	169.7 (2)
F2—C9—C10—F3	145.4 (3)	F1—C9—C8—C9'	−29.7 (18)
C8—C9—C10—F3	−93.8 (3)	F2—C9—C8—C9'	−148 (2)
F1—C9—C10—C11	146.6 (3)	C10—C9—C8—C9'	92 (2)
F2—C9—C10—C11	−96.9 (3)	C6—C8—C12—C13	−4.6 (3)
C8—C9—C10—C11	23.8 (3)	C9'—C8—C12—C13	165.0 (5)
F2'—C9'—C10'—F3'	95.5 (11)	C9—C8—C12—C13	−177.7 (2)
F1'—C9'—C10'—F3'	−22.6 (13)	C6—C8—C12—C11'	−175.7 (6)
C8—C9'—C10'—F3'	−147.0 (10)	C9'—C8—C12—C11'	−6.1 (7)
F2'—C9'—C10'—F4'	−26.6 (13)	C9—C8—C12—C11'	11.2 (6)
F1'—C9'—C10'—F4'	−144.7 (9)	C6—C8—C12—C11	174.6 (2)
C8—C9'—C10'—F4'	90.9 (11)	C9'—C8—C12—C11	−15.8 (5)
F2'—C9'—C10'—C11'	−146.8 (9)	C9—C8—C12—C11	1.5 (3)
F1'—C9'—C10'—C11'	95.0 (10)	F6'—C11'—C12—C8	−132.9 (9)
C8—C9'—C10'—C11'	−29.3 (10)	F5'—C11'—C12—C8	108.7 (10)
F4—C10—C11—F5	92.5 (3)	C10'—C11'—C12—C8	−13.7 (10)
F3—C10—C11—F5	−27.2 (3)	F6'—C11'—C12—C13	55.3 (12)
C9—C10—C11—F5	−144.9 (2)	F5'—C11'—C12—C13	−63.1 (12)
F4—C10—C11—F6	−24.1 (3)	C10'—C11'—C12—C13	174.5 (6)
F3—C10—C11—F6	−143.8 (3)	F6'—C11'—C12—C11	−13 (3)
C9—C10—C11—F6	98.5 (3)	F5'—C11'—C12—C11	−131 (4)
F4—C10—C11—C12	−145.4 (2)	C10'—C11'—C12—C11	106 (4)
F3—C10—C11—C12	94.9 (3)	F5—C11—C12—C8	134.4 (2)
C9—C10—C11—C12	−22.8 (3)	F6—C11—C12—C8	−105.5 (3)
F3'—C10'—C11'—F6'	−95.1 (13)	C10—C11—C12—C8	13.9 (3)
F4'—C10'—C11'—F6'	24.1 (13)	F5—C11—C12—C13	−46.3 (3)
C9'—C10'—C11'—F6'	145.4 (10)	F6—C11—C12—C13	73.8 (3)
F3'—C10'—C11'—F5'	26.3 (13)	C10—C11—C12—C13	−166.80 (19)
F4'—C10'—C11'—F5'	145.5 (10)	F5—C11—C12—C11'	71 (4)
C9'—C10'—C11'—F5'	−93.2 (10)	F6—C11—C12—C11'	−169 (4)
F3'—C10'—C11'—C12	146.9 (10)	C10—C11—C12—C11'	−49 (4)
F4'—C10'—C11'—C12	−93.8 (11)	C8—C12—C13—C16	−52.8 (3)
C9'—C10'—C11'—C12	27.4 (12)	C11'—C12—C13—C16	117.0 (7)
C7—O1—C1—C2	28.8 (3)	C11—C12—C13—C16	128.1 (2)
C7—O1—C1—C6	−151.1 (2)	C8—C12—C13—C14	131.0 (2)
O1—C1—C2—C3	−179.1 (2)	C11'—C12—C13—C14	−59.2 (7)
C6—C1—C2—C3	0.8 (4)	C11—C12—C13—C14	−48.2 (3)
C1—C2—C3—C4	0.3 (4)	C16—C13—C14—C15	0.6 (2)
C2—C3—C4—C5	−0.6 (4)	C12—C13—C14—C15	177.27 (17)
C3—C4—C5—C6	−0.2 (3)	C13—C14—C15—C18	178.83 (18)
C4—C5—C6—C1	1.3 (3)	C13—C14—C15—S1	−0.5 (2)
C4—C5—C6—C8	179.1 (2)	C16—S1—C15—C14	0.21 (16)
O1—C1—C6—C5	178.30 (19)	C16—S1—C15—C18	−179.19 (16)
C2—C1—C6—C5	−1.6 (3)	C14—C13—C16—C17	176.5 (2)
O1—C1—C6—C8	0.5 (3)	C12—C13—C16—C17	−0.1 (3)
C2—C1—C6—C8	−179.4 (2)	C14—C13—C16—S1	−0.4 (2)
C5—C6—C8—C12	120.1 (2)	C12—C13—C16—S1	−177.03 (14)
C1—C6—C8—C12	−62.1 (3)	C15—S1—C16—C13	0.14 (16)
C5—C6—C8—C9'	−49.3 (5)	C15—S1—C16—C17	−177.15 (18)
C1—C6—C8—C9'	128.5 (5)	C14—C15—C18—C19	−171.0 (2)
C5—C6—C8—C9	−67.4 (3)	S1—C15—C18—C19	8.3 (3)
C1—C6—C8—C9	110.4 (2)	C14—C15—C18—C23	8.5 (3)
F2'—C9'—C8—C12	137.0 (8)	S1—C15—C18—C23	−172.26 (16)
F1'—C9'—C8—C12	−98.6 (9)	C23—C18—C19—C20	−0.8 (4)
C10'—C9'—C8—C12	23.2 (8)	C15—C18—C19—C20	178.7 (2)
F2'—C9'—C8—C6	−52.0 (10)	C18—C19—C20—C21	0.9 (4)
F1'—C9'—C8—C6	72.5 (10)	C19—C20—C21—C22	−0.2 (4)
C10'—C9'—C8—C6	−165.8 (6)	C20—C21—C22—C23	−0.6 (4)
F2'—C9'—C8—C9	59.4 (16)	C20—C21—C22—Cl1	179.5 (2)
F1'—C9'—C8—C9	−176 (3)	C21—C22—C23—C18	0.6 (3)
C10'—C9'—C8—C9	−54.4 (18)	Cl1—C22—C23—C18	−179.50 (17)
F1—C9—C8—C12	−138.6 (3)	C19—C18—C23—C22	0.1 (3)
F2—C9—C8—C12	103.1 (3)	C15—C18—C23—C22	−179.40 (19)

Experimental details

Crystal data
Chemical formula	C₂₃H₁₅ClF₆OS
M_r	488.86
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	9.4057 (10), 10.2900 (11), 11.9548 (13)
α, β, γ (°)	83.529 (1), 71.564 (1), 80.639 (1)
V (Å³)	1080.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.49 × 0.45 × 0.33

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.851, 0.896
No. of measured, independent and observed [I > 2σ(I)] reflections	8254, 3997, 3358
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.03
No. of reflections	3997
No. of parameters	321
No. of restraints	553
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.36

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Science Fund of the Education Office of Jiangxi (grant Nos. GJJ09306 and GJJ09302) and the Youth Science Fund of the Education Office of Jiangxi (grant Nos. GJJ09567 and GJJ09572).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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