4-{2-[5-(3,5-Difluoro­phen­yl)-2-methyl­thio­phen-3-yl]-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-en-1-yl}-1,5-dimethyl­pyrrole-2-carbonitrile

Liu, G.; Wang, X.; Fan, C.

doi:10.1107/S1600536811009780

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o939

doi:10.1107/S1600536811009780

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4-{2-[5-(3,5-Difluorophenyl)-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl}-1,5-dimethylpyrrole-2-carbonitrile

Gang Liu,^a Xiao-mei Wang ^a ^* and Cong-bin Fan ^a

^aCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China
^*Correspondence e-mail: fan200203@163.com

(Received 27 February 2011; accepted 15 March 2011; online 23 March 2011)

In the title compound, C₂₃H₁₄F₈N₂S, the dihedral angles between the pyrrole and thiophene groups and the almost planar C—C=C—C unit of the cyclopentene ring (r.m.s. deviation = 0.4193 Å) are 43.6 (5) and 50.1 (2)°, respectively. The distance of 3.612 (3) Å between the potentially reactive C atoms of the two heteroaryl substituents is short enough to enable a photocyclization reaction.

Related literature

The title compound belongs to a new family of organic photochromic diarylethene compounds with an unsymmetrically substituted hexafluorocyclopentene unit. For background to these compounds, see: Pu et al. (2007 ); Liu et al. (2011 ). For details of the synthesis, see: Fan et al. (2011 ).

Experimental

Crystal data

C₂₃H₁₄F₈N₂S
M_r = 502.42
Monoclinic, P 2₁ /c
a = 11.873 (2) Å
b = 12.063 (2) Å
c = 16.208 (3) Å
β = 109.225 (3)°
V = 2191.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 294 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.947, T_max = 0.973
10859 measured reflections
3870 independent reflections
2075 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.108
S = 1.00
3870 reflections
310 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009780/gk2352sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009780/gk2352Isup2.hkl

checkCIF report

Comment top

The title compound when dissolved in hexane shows photochromism. Upon irradiation with 365 nm light, the colorless hexane solution turns blue rapidly. The blue compound displays an absorption maximum at 592 nm. Upon irradiation with visible light with wavelength longer than 510 nm, the blue hexane solution reverts to its initial colorless state; a colorless hexane solution of the title compound has two absorption maximum at 253 nm and 294 nm. In a polymethylmethacrylate amorphous film, the title diarylethene also exhibits photochromism similar to that in hexane.

Related literature top

The title compound belongs to a new family of organic photochromic diarylethene compounds with an unsymmetrically substituted hexafluorocyclopentene unit. For background to these compounds, see: Pu et al. (2007); Liu et al. (2011). For details of the synthesis, see: Fan et al. (2011).

Experimental top

To a tetrahydrofuran solution of 1-bromo-3,5-difluorobenzene (1.93 g, 10.0 mmol) was added 3-bromo-2-methyl-5-thienylboronic acid (2.50 g, 11.3 mmol) (Fan et al., 2011) in the presence of Pd(PPh₃)₄ (0.3 g) and Na₂CO₃ (6.4 g, 60 mmol) in 20 ml H₂O. After refluxing for 15 h, the product, 3-Bromo-2-methyl-5-(3,5-difluorophenyl)thiophene (1.94 g, 6.73 mmol), was collected and dried (yield 67.3%). This compound (0.67 g, 2.3 mmol) was reacted with 1-(2-cyano-1,5-dimethyl-4-pyrrol-1-yl)-3,3,4,4,5,5- hexafluorocyclopent-1-ene (0.66 g, 2.30 mmol)(Liu et al., 2011) and with n-butyl lithium 2.5 M in hexane (0.92 ml, 2.30 mmol) at 195 K under a nitrogen atmosphere. After an hour, the reaction was quenched by addition of water. The solid product was purified by column chromatography on silica with petroleum ether as the eluent to give the title compound (0.55 g, 1.10 mmol) in 47.8% yield. Analysis calc. for C₂₃H₁₄F₈N₂S: C 54.98, H, 2.81%; fFound C 55.02, H 2.95%.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

4-{2-[5-(3,5-Difluorophenyl)-2-methylthiophen-3-yl]-3,3,4,4,5,5- hexafluorocyclopent-1-en-1-yl}-1,5-dimethylpyrrole-2-carbonitrile top

Crystal data top

C₂₃H₁₄F₈N₂S	F(000) = 1016
M_r = 502.42	D_x = 1.523 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1969 reflections
a = 11.873 (2) Å	θ = 2.2–21.0°
b = 12.063 (2) Å	µ = 0.23 mm⁻¹
c = 16.208 (3) Å	T = 294 K
β = 109.225 (3)°	Block, colourless
V = 2191.9 (7) Å³	0.24 × 0.20 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3870 independent reflections
Radiation source: fine-focus sealed tube	2075 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
T_min = 0.947, T_max = 0.973	k = −14→7
10859 measured reflections	l = −19→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0294P)² + 1.1725P] where P = (F_o² + 2F_c²)/3
3870 reflections	(Δ/σ)_max < 0.001
310 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₃H₁₄F₈N₂S	V = 2191.9 (7) Å³
M_r = 502.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.873 (2) Å	µ = 0.23 mm⁻¹
b = 12.063 (2) Å	T = 294 K
c = 16.208 (3) Å	0.24 × 0.20 × 0.12 mm
β = 109.225 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3870 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2075 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.973	R_int = 0.052
10859 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.00	Δρ_max = 0.22 e Å⁻³
3870 reflections	Δρ_min = −0.23 e Å⁻³
310 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.20592 (8)	0.64459 (8)	0.08798 (6)	0.0544 (3)
F1	−0.1023 (3)	0.5715 (2)	−0.22785 (15)	0.1251 (10)
F2	−0.3477 (2)	0.7314 (2)	−0.08674 (16)	0.1138 (9)
F3	0.12870 (18)	1.04692 (16)	0.16690 (13)	0.0782 (7)
F4	0.31802 (19)	1.04374 (18)	0.19007 (13)	0.0794 (7)
F5	0.1543 (2)	1.10471 (19)	0.32403 (14)	0.0904 (7)
F6	0.3169 (2)	1.17628 (17)	0.31582 (13)	0.0908 (8)
F7	0.3056 (2)	1.01110 (17)	0.45684 (13)	0.0798 (7)
F8	0.44533 (17)	1.01423 (16)	0.39904 (12)	0.0738 (6)
N1	0.2949 (2)	0.6232 (2)	0.45199 (17)	0.0506 (7)
N2	0.5482 (3)	0.5675 (3)	0.6326 (2)	0.0928 (12)
C1	−0.1419 (3)	0.7236 (3)	−0.0150 (2)	0.0584 (10)
H1	−0.1522	0.7596	0.0328	0.070*
C2	−0.2385 (3)	0.7008 (4)	−0.0874 (3)	0.0714 (12)
C3	−0.2293 (4)	0.6494 (3)	−0.1595 (3)	0.0772 (13)
H3	−0.2957	0.6352	−0.2082	0.093*
C4	−0.1168 (4)	0.6197 (3)	−0.1564 (3)	0.0771 (12)
C5	−0.0167 (3)	0.6391 (3)	−0.0855 (2)	0.0630 (10)
H5	0.0580	0.6165	−0.0860	0.076*
C6	−0.0287 (3)	0.6927 (3)	−0.0134 (2)	0.0485 (9)
C7	0.0764 (3)	0.7213 (3)	0.06179 (19)	0.0442 (8)
C8	0.0902 (3)	0.8070 (3)	0.11854 (19)	0.0477 (9)
H8	0.0303	0.8583	0.1150	0.057*
C9	0.2049 (3)	0.8111 (3)	0.18408 (18)	0.0433 (8)
C10	0.2779 (3)	0.7270 (3)	0.17555 (19)	0.0459 (8)
C11	0.4044 (3)	0.7020 (3)	0.2296 (2)	0.0637 (10)
H11A	0.4424	0.7685	0.2578	0.096*
H11B	0.4464	0.6739	0.1925	0.096*
H11C	0.4053	0.6475	0.2729	0.096*
C12	0.2404 (2)	0.8972 (3)	0.25172 (19)	0.0425 (8)
C13	0.2332 (3)	1.0168 (3)	0.2267 (2)	0.0513 (9)
C14	0.2579 (3)	1.0803 (3)	0.3117 (2)	0.0552 (9)
C15	0.3261 (3)	0.9968 (3)	0.3807 (2)	0.0515 (9)
C16	0.2898 (2)	0.8857 (3)	0.33946 (19)	0.0412 (8)
C17	0.3125 (3)	0.7868 (3)	0.39402 (18)	0.0421 (8)
C18	0.2400 (3)	0.6945 (3)	0.3864 (2)	0.0458 (8)
C19	0.1198 (3)	0.6706 (3)	0.3228 (2)	0.0636 (10)
H19A	0.1270	0.6179	0.2804	0.095*
H19B	0.0852	0.7379	0.2938	0.095*
H19C	0.0697	0.6405	0.3532	0.095*
C20	0.4144 (3)	0.7692 (3)	0.4683 (2)	0.0487 (9)
H20	0.4781	0.8178	0.4902	0.058*
C21	0.4025 (3)	0.6688 (3)	0.5020 (2)	0.0503 (9)
C22	0.4826 (4)	0.6117 (3)	0.5744 (3)	0.0648 (10)
C23	0.2477 (3)	0.5162 (3)	0.4684 (2)	0.0763 (12)
H23A	0.1777	0.5282	0.4845	0.115*
H23B	0.3070	0.4786	0.5150	0.115*
H23C	0.2274	0.4717	0.4165	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0588 (6)	0.0534 (6)	0.0508 (5)	0.0051 (5)	0.0180 (4)	−0.0076 (5)
F1	0.156 (2)	0.127 (2)	0.0683 (16)	−0.0037 (19)	0.0043 (16)	−0.0514 (16)
F2	0.0529 (15)	0.164 (3)	0.1049 (18)	−0.0014 (16)	−0.0008 (13)	0.0156 (18)
F3	0.0771 (15)	0.0648 (14)	0.0678 (13)	0.0198 (11)	−0.0099 (11)	−0.0011 (11)
F4	0.0955 (17)	0.0751 (16)	0.0794 (15)	−0.0045 (13)	0.0449 (13)	0.0115 (12)
F5	0.0856 (17)	0.0976 (19)	0.0857 (16)	0.0291 (14)	0.0254 (13)	−0.0200 (14)
F6	0.1210 (19)	0.0524 (14)	0.0784 (15)	−0.0257 (13)	0.0048 (13)	0.0062 (12)
F7	0.1296 (19)	0.0614 (14)	0.0532 (13)	−0.0118 (13)	0.0366 (13)	−0.0117 (11)
F8	0.0577 (13)	0.0680 (14)	0.0752 (14)	−0.0230 (11)	−0.0058 (10)	0.0032 (12)
N1	0.0634 (19)	0.0405 (17)	0.0494 (17)	−0.0112 (15)	0.0208 (15)	−0.0042 (15)
N2	0.102 (3)	0.081 (3)	0.075 (2)	0.010 (2)	0.002 (2)	0.016 (2)
C1	0.056 (2)	0.068 (3)	0.046 (2)	−0.007 (2)	0.0096 (18)	0.0015 (19)
C2	0.057 (3)	0.078 (3)	0.066 (3)	−0.015 (2)	0.003 (2)	0.018 (2)
C3	0.085 (3)	0.065 (3)	0.055 (3)	−0.022 (3)	−0.013 (2)	0.006 (2)
C4	0.104 (4)	0.064 (3)	0.052 (3)	−0.014 (3)	0.010 (3)	−0.015 (2)
C5	0.069 (2)	0.063 (3)	0.055 (2)	−0.009 (2)	0.017 (2)	−0.012 (2)
C6	0.055 (2)	0.049 (2)	0.038 (2)	−0.0065 (18)	0.0112 (17)	0.0029 (17)
C7	0.0455 (19)	0.047 (2)	0.0369 (18)	−0.0029 (16)	0.0097 (15)	−0.0031 (17)
C8	0.0425 (19)	0.052 (2)	0.0449 (19)	0.0078 (16)	0.0097 (16)	−0.0023 (18)
C9	0.0421 (19)	0.050 (2)	0.0345 (18)	0.0041 (17)	0.0083 (15)	−0.0031 (16)
C10	0.0448 (19)	0.053 (2)	0.0412 (19)	0.0045 (17)	0.0163 (15)	0.0009 (17)
C11	0.048 (2)	0.076 (3)	0.063 (2)	0.015 (2)	0.0135 (18)	0.000 (2)
C12	0.0367 (18)	0.050 (2)	0.0378 (19)	0.0023 (16)	0.0078 (15)	−0.0015 (17)
C13	0.044 (2)	0.057 (2)	0.048 (2)	0.0072 (18)	0.0083 (17)	0.0036 (19)
C14	0.055 (2)	0.046 (2)	0.060 (2)	−0.0015 (19)	0.0124 (19)	−0.0044 (19)
C15	0.053 (2)	0.050 (2)	0.045 (2)	−0.0128 (18)	0.0073 (17)	−0.0046 (19)
C16	0.0323 (17)	0.048 (2)	0.0430 (19)	−0.0066 (15)	0.0118 (15)	−0.0011 (17)
C17	0.0427 (19)	0.046 (2)	0.0364 (18)	−0.0034 (17)	0.0115 (15)	−0.0006 (16)
C18	0.0460 (19)	0.048 (2)	0.045 (2)	−0.0111 (18)	0.0171 (16)	−0.0070 (18)
C19	0.055 (2)	0.069 (3)	0.064 (2)	−0.023 (2)	0.0148 (18)	−0.013 (2)
C20	0.050 (2)	0.048 (2)	0.045 (2)	−0.0089 (17)	0.0101 (17)	−0.0056 (18)
C21	0.052 (2)	0.051 (2)	0.045 (2)	−0.0011 (19)	0.0112 (17)	−0.0002 (18)
C22	0.074 (3)	0.054 (2)	0.061 (3)	0.001 (2)	0.015 (2)	0.000 (2)
C23	0.098 (3)	0.056 (2)	0.079 (3)	−0.025 (2)	0.034 (2)	0.007 (2)

Geometric parameters (Å, º) top

S1—C10	1.713 (3)	C8—H8	0.9300
S1—C7	1.724 (3)	C9—C10	1.370 (4)
F1—C4	1.357 (4)	C9—C12	1.467 (4)
F2—C2	1.352 (4)	C10—C11	1.499 (4)
F3—C13	1.349 (3)	C11—H11A	0.9600
F4—C13	1.366 (4)	C11—H11B	0.9600
F5—C14	1.343 (4)	C11—H11C	0.9600
F6—C14	1.343 (4)	C12—C16	1.355 (4)
F7—C15	1.345 (4)	C12—C13	1.494 (4)
F8—C15	1.364 (3)	C13—C14	1.518 (4)
N1—C18	1.357 (4)	C14—C15	1.524 (5)
N1—C21	1.381 (4)	C15—C16	1.496 (4)
N1—C23	1.467 (4)	C16—C17	1.457 (4)
N2—C22	1.139 (4)	C17—C18	1.387 (4)
C1—C2	1.372 (5)	C17—C20	1.414 (4)
C1—C6	1.387 (4)	C18—C19	1.487 (4)
C1—H1	0.9300	C19—H19A	0.9600
C2—C3	1.359 (5)	C19—H19B	0.9600
C3—C4	1.367 (5)	C19—H19C	0.9600
C3—H3	0.9300	C20—C21	1.355 (4)
C4—C5	1.375 (5)	C20—H20	0.9300
C5—C6	1.383 (4)	C21—C22	1.422 (5)
C5—H5	0.9300	C23—H23A	0.9600
C6—C7	1.470 (4)	C23—H23B	0.9600
C7—C8	1.357 (4)	C23—H23C	0.9600
C8—C9	1.426 (4)

C10—S1—C7	93.06 (15)	F4—C13—C12	111.3 (3)
C18—N1—C21	108.7 (3)	F3—C13—C14	112.0 (3)
C18—N1—C23	125.9 (3)	F4—C13—C14	109.0 (3)
C21—N1—C23	125.4 (3)	C12—C13—C14	105.3 (3)
C2—C1—C6	119.6 (4)	F5—C14—F6	107.0 (3)
C2—C1—H1	120.2	F5—C14—C13	109.4 (3)
C6—C1—H1	120.2	F6—C14—C13	114.9 (3)
F2—C2—C3	118.7 (4)	F5—C14—C15	109.1 (3)
F2—C2—C1	118.2 (4)	F6—C14—C15	113.0 (3)
C3—C2—C1	123.1 (4)	C13—C14—C15	103.3 (3)
C2—C3—C4	116.3 (4)	F7—C15—F8	105.5 (3)
C2—C3—H3	121.9	F7—C15—C16	114.3 (3)
C4—C3—H3	121.9	F8—C15—C16	111.1 (3)
F1—C4—C3	118.6 (4)	F7—C15—C14	112.1 (3)
F1—C4—C5	117.9 (4)	F8—C15—C14	108.7 (3)
C3—C4—C5	123.4 (4)	C16—C15—C14	105.0 (3)
C4—C5—C6	119.0 (4)	C12—C16—C17	130.5 (3)
C4—C5—H5	120.5	C12—C16—C15	109.8 (3)
C6—C5—H5	120.5	C17—C16—C15	119.6 (3)
C5—C6—C1	118.6 (3)	C18—C17—C20	106.7 (3)
C5—C6—C7	121.0 (3)	C18—C17—C16	128.1 (3)
C1—C6—C7	120.3 (3)	C20—C17—C16	125.1 (3)
C8—C7—C6	128.4 (3)	N1—C18—C17	108.3 (3)
C8—C7—S1	110.1 (2)	N1—C18—C19	121.6 (3)
C6—C7—S1	121.5 (2)	C17—C18—C19	130.0 (3)
C7—C8—C9	113.8 (3)	C18—C19—H19A	109.5
C7—C8—H8	123.1	C18—C19—H19B	109.5
C9—C8—H8	123.1	H19A—C19—H19B	109.5
C10—C9—C8	112.3 (3)	C18—C19—H19C	109.5
C10—C9—C12	124.3 (3)	H19A—C19—H19C	109.5
C8—C9—C12	123.3 (3)	H19B—C19—H19C	109.5
C9—C10—C11	129.4 (3)	C21—C20—C17	107.6 (3)
C9—C10—S1	110.7 (2)	C21—C20—H20	126.2
C11—C10—S1	119.8 (2)	C17—C20—H20	126.2
C10—C11—H11A	109.5	C20—C21—N1	108.6 (3)
C10—C11—H11B	109.5	C20—C21—C22	129.4 (3)
H11A—C11—H11B	109.5	N1—C21—C22	122.0 (3)
C10—C11—H11C	109.5	N2—C22—C21	178.8 (4)
H11A—C11—H11C	109.5	N1—C23—H23A	109.5
H11B—C11—H11C	109.5	N1—C23—H23B	109.5
C16—C12—C9	129.1 (3)	H23A—C23—H23B	109.5
C16—C12—C13	110.4 (3)	N1—C23—H23C	109.5
C9—C12—C13	120.3 (3)	H23A—C23—H23C	109.5
F3—C13—F4	105.0 (3)	H23B—C23—H23C	109.5
F3—C13—C12	114.3 (3)

C6—C1—C2—F2	179.6 (3)	C12—C13—C14—F6	146.1 (3)
C6—C1—C2—C3	−0.6 (6)	F3—C13—C14—C15	147.3 (3)
F2—C2—C3—C4	−179.6 (3)	F4—C13—C14—C15	−97.0 (3)
C1—C2—C3—C4	0.6 (6)	C12—C13—C14—C15	22.5 (3)
C2—C3—C4—F1	−177.8 (3)	F5—C14—C15—F7	−32.5 (4)
C2—C3—C4—C5	0.2 (6)	F6—C14—C15—F7	86.4 (4)
F1—C4—C5—C6	177.1 (3)	C13—C14—C15—F7	−148.8 (3)
C3—C4—C5—C6	−0.9 (6)	F5—C14—C15—F8	−148.8 (3)
C4—C5—C6—C1	0.9 (5)	F6—C14—C15—F8	−29.9 (4)
C4—C5—C6—C7	−176.3 (3)	C13—C14—C15—F8	94.9 (3)
C2—C1—C6—C5	−0.2 (5)	F5—C14—C15—C16	92.2 (3)
C2—C1—C6—C7	177.0 (3)	F6—C14—C15—C16	−148.9 (3)
C5—C6—C7—C8	150.7 (3)	C13—C14—C15—C16	−24.1 (3)
C1—C6—C7—C8	−26.4 (5)	C9—C12—C16—C17	−6.6 (5)
C5—C6—C7—S1	−28.1 (4)	C13—C12—C16—C17	178.4 (3)
C1—C6—C7—S1	154.7 (3)	C9—C12—C16—C15	172.1 (3)
C10—S1—C7—C8	0.5 (3)	C13—C12—C16—C15	−2.9 (4)
C10—S1—C7—C6	179.5 (3)	F7—C15—C16—C12	140.7 (3)
C6—C7—C8—C9	−179.4 (3)	F8—C15—C16—C12	−99.9 (3)
S1—C7—C8—C9	−0.5 (3)	C14—C15—C16—C12	17.5 (4)
C7—C8—C9—C10	0.3 (4)	F7—C15—C16—C17	−40.4 (4)
C7—C8—C9—C12	179.3 (3)	F8—C15—C16—C17	78.9 (4)
C8—C9—C10—C11	179.3 (3)	C14—C15—C16—C17	−163.7 (3)
C12—C9—C10—C11	0.3 (5)	C12—C16—C17—C18	−40.4 (5)
C8—C9—C10—S1	0.1 (3)	C15—C16—C17—C18	141.1 (3)
C12—C9—C10—S1	−178.9 (2)	C12—C16—C17—C20	141.8 (3)
C7—S1—C10—C9	−0.3 (3)	C15—C16—C17—C20	−36.7 (4)
C7—S1—C10—C11	−179.6 (3)	C21—N1—C18—C17	0.0 (4)
C10—C9—C12—C16	−52.0 (5)	C23—N1—C18—C17	179.1 (3)
C8—C9—C12—C16	129.1 (3)	C21—N1—C18—C19	−177.9 (3)
C10—C9—C12—C13	122.7 (3)	C23—N1—C18—C19	1.2 (5)
C8—C9—C12—C13	−56.2 (4)	C20—C17—C18—N1	−0.7 (3)
C16—C12—C13—F3	−136.2 (3)	C16—C17—C18—N1	−178.8 (3)
C9—C12—C13—F3	48.3 (4)	C20—C17—C18—C19	177.0 (3)
C16—C12—C13—F4	105.1 (3)	C16—C17—C18—C19	−1.1 (6)
C9—C12—C13—F4	−70.5 (4)	C18—C17—C20—C21	1.1 (4)
C16—C12—C13—C14	−12.9 (4)	C16—C17—C20—C21	179.3 (3)
C9—C12—C13—C14	171.6 (3)	C17—C20—C21—N1	−1.1 (4)
F3—C13—C14—F5	31.2 (4)	C17—C20—C21—C22	177.4 (3)
F4—C13—C14—F5	146.9 (3)	C18—N1—C21—C20	0.7 (4)
C12—C13—C14—F5	−93.6 (3)	C23—N1—C21—C20	−178.4 (3)
F3—C13—C14—F6	−89.1 (4)	C18—N1—C21—C22	−178.0 (3)
F4—C13—C14—F6	26.6 (4)	C23—N1—C21—C22	3.0 (5)

Experimental details

Crystal data
Chemical formula	C₂₃H₁₄F₈N₂S
M_r	502.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	11.873 (2), 12.063 (2), 16.208 (3)
β (°)	109.225 (3)
V (Å³)	2191.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	10859, 3870, 2075
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.108, 1.00
No. of reflections	3870
No. of parameters	310
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (grant Nos. 50673070, 50973077), the Natural Science Foundation of Jiangxi Province (2010GZH0040) and the Science and Technology Development Project of Suzhou (SYJG0931).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fan, C.-B., Yang, P., Wang, X.-M., Liu, G., Jiang, X.-X., Chen, H.-Z., Tao, X.-T., Wang, M. & Jiang, M.-H. (2011). Sol. Energy Mater. Sol. Cells, 95, 992–1000. CrossRef CAS Google Scholar
Liu, G., Pu, S.-Z., Wang, X.-M., Liu, W.-J. & Yang, T.-S. (2011). Dyes Pigments, 90, 71–81. CrossRef CAS Google Scholar
Pu, S.-Z., Liu, G., Shen, L. & Xu, J.-K. (2007). Org. Lett., 9, 2139–2142. Web of Science CrossRef PubMed CAS 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

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