5-n-Butyl-4-[2-(2-ethyl-1-benzothio-phen-3-yl)-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-en-1-yl]thio-phene-2-carbaldehyde.

The title compound, C(24)H(20)F(6)OS(2), exhibiting photochromic behaviour, has thienyl and benzothienyl substituents attached to the double-bond C atoms of the envelope-shaped cyclo-pentene ring. The mean planes of aromatic systems form dihedral angles of 43.0 (1) (thien-yl) and 73.8 (1)° (benzothien-yl) with the mean plane of the C-C=C-C portion of the cyclo-pentene 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 = 502.52

Triclinic,

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 ▶); 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 ▶).

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

C24H20F6OS2	Z = 2
Mr = 502.52	F000 = 516
Triclinic, P1	Dx = 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 = 2.5–28.2º
c = 12.019 (1) Å	µ = 0.29 mm−1
α = 113.126 (1)º	T = 296 (2) K
β = 96.882 (1)º	Block, colourless
γ = 103.542 (1)º	0.43 × 0.43 × 0.43 mm
V = 1157.5 (2) Å3

Bruker SMART area-detector diffractometer	3669 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Monochromator: graphite	θmax = 27.5º
T = 296(2) K	θmin = 2.5º
φ and ω scans	h = −12→13
Absorption correction: None	k = −14→14
10086 measured reflections	l = −15→15
5195 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-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 reflections	Δρmax = 0.34 e Å−3
318 parameters	Δρmin = −0.25 e Å−3
30 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	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*

	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)

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)