1,2-Bis[5-(4-cyano-phen-yl)-2-methyl-3-thien-yl]-3,3,4,4,5,5-hexa-fluoro-cyclo-pent-1-ene: a photochromic diaryl-ethene compound.

The mol-ecules of the title compound, C(29)H(16)F(6)N(2)S(2), a photochromic dithienylethene with 4-cyano-phenyl substituents, adopt an anti-parallel arrangement that is reponsible for photoactivity. The mol-ecule lies on a twofold rotation axis. The dihedral angle between the nearly planar cyclo-pentenyl and heteroaryl rings is 142.5 (3)°, and that between the heteroaryl and benzene rings is 22.4 (3)°. The distance between the heteroaryl rings of adjacent mol-ecules is 3.601 (2) Å, indicating a π-π interaction.

Related literature

For a review of dithienylethyl­enes as photochromic compounds, see: Irie (2000 ▶). For phenyl-substituted derivatives, see: Pu, Liu et al. (2005 ▶); Pu, Yang et al. (2005 ▶). For another similar structure, see: Kobatake et al. (2004 ▶). For the manifestation of possible photochromic activity in relation to the conformation, see: Woodward & Hoffmann (1970 ▶).

Experimental

Crystal data

C29H16F6N2S2

M = 570.56

Monoclinic,

a = 24.987 (10) Å

b = 9.276 (4) Å

c = 10.774 (4) Å

β = 95.911 (7)°

V = 2483.8 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 113 (2) K

0.36 × 0.20 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.905, T max = 0.972

9917 measured reflections

2437 independent reflections

2130 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.145

S = 1.06

2437 reflections

180 parameters

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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: CrystalStructure.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808011653/ng2448sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011653/ng2448Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H16F6N2S2	F000 = 1160
Mr = 570.56	Dx = 1.526 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -C2yc	Cell parameters from 3563 reflections
a = 24.987 (10) Å	θ = 1.6–27.9º
b = 9.276 (4) Å	µ = 0.28 mm−1
c = 10.774 (4) Å	T = 113 (2) K
β = 95.911 (7)º	Block, colorless
V = 2483.8 (17) Å3	0.36 × 0.20 × 0.10 mm
Z = 4

Rigaku Saturn diffractometer	2437 independent reflections
Radiation source: rotating anode	2130 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.032
Detector resolution: 7.31 pixels mm-1	θmax = 26.0º
T = 113(2) K	θmin = 1.6º
ω scans	h = −30→30
Absorption correction: multi-scan(Jacobson, 1998)	k = −11→11
Tmin = 0.905, Tmax = 0.972	l = −12→13
9917 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.057	w = 1/[σ2(Fo2) + (0.0692P)2 + 6.3864P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.90 e Å−3
2437 reflections	Δρmin = −0.65 e Å−3
180 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (9)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
S1	0.12440 (3)	0.06080 (7)	0.81522 (6)	0.0293 (2)
F1	0.04313 (8)	0.57014 (18)	0.94258 (16)	0.0469 (5)
F2	0.09200 (7)	0.57943 (19)	0.7907 (2)	0.0607 (7)
F3	−0.02249 (10)	0.7331 (3)	0.8302 (2)	0.0846 (10)
N1	0.34207 (11)	0.1164 (3)	1.4057 (3)	0.0492 (7)
C1	0.13504 (10)	0.1761 (3)	0.9418 (2)	0.0252 (6)
C2	0.09893 (10)	0.2871 (3)	0.9294 (2)	0.0248 (6)
H2	0.0981	0.3621	0.9893	0.030*
C3	0.06264 (10)	0.2802 (3)	0.8183 (2)	0.0244 (6)
C4	0.07183 (10)	0.1622 (3)	0.7454 (2)	0.0270 (6)
C5	0.17915 (10)	0.1560 (3)	1.0408 (2)	0.0248 (6)
C6	0.17718 (11)	0.2247 (3)	1.1548 (2)	0.0281 (6)
H6	0.1462	0.2791	1.1693	0.034*
C7	0.21958 (11)	0.2150 (3)	1.2473 (3)	0.0308 (6)
H7	0.2177	0.2624	1.3248	0.037*
C8	0.26506 (10)	0.1355 (3)	1.2265 (3)	0.0287 (6)
C9	0.26789 (11)	0.0656 (3)	1.1132 (3)	0.0292 (6)
H9	0.2990	0.0118	1.0988	0.035*
C10	0.22495 (11)	0.0750 (3)	1.0215 (3)	0.0286 (6)
H10	0.2265	0.0260	0.9445	0.034*
C11	0.30895 (11)	0.1252 (3)	1.3245 (3)	0.0350 (7)
C12	0.02472 (10)	0.3973 (3)	0.7823 (2)	0.0228 (5)
C13	0.04203 (10)	0.5483 (3)	0.8172 (3)	0.0274 (6)
C14	0.0000	0.6490 (4)	0.7500	0.0306 (8)
C15	0.04599 (12)	0.1178 (3)	0.6201 (3)	0.0331 (6)
H15A	0.0714	0.0602	0.5775	0.040*
H15B	0.0358	0.2039	0.5704	0.040*
H15C	0.0138	0.0603	0.6302	0.040*

	U11	U22	U33	U12	U13	U23
S1	0.0312 (4)	0.0264 (4)	0.0297 (4)	0.0058 (3)	−0.0006 (3)	−0.0016 (3)
F1	0.0697 (13)	0.0316 (9)	0.0346 (10)	0.0099 (8)	−0.0174 (9)	−0.0094 (7)
F2	0.0327 (10)	0.0317 (10)	0.122 (2)	−0.0050 (8)	0.0302 (11)	0.0038 (11)
F3	0.0843 (17)	0.0847 (17)	0.0741 (15)	0.0586 (14)	−0.0430 (13)	−0.0557 (13)
N1	0.0378 (15)	0.0602 (18)	0.0466 (16)	−0.0076 (13)	−0.0110 (12)	0.0141 (14)
C1	0.0246 (12)	0.0227 (12)	0.0283 (13)	0.0003 (10)	0.0023 (10)	0.0013 (10)
C2	0.0240 (12)	0.0234 (12)	0.0269 (13)	0.0005 (10)	0.0017 (10)	0.0004 (10)
C3	0.0232 (12)	0.0235 (13)	0.0263 (13)	−0.0004 (10)	0.0012 (10)	0.0023 (10)
C4	0.0277 (13)	0.0263 (13)	0.0268 (13)	0.0018 (10)	0.0012 (10)	0.0016 (11)
C5	0.0233 (12)	0.0221 (12)	0.0289 (13)	−0.0006 (10)	0.0016 (10)	0.0044 (10)
C6	0.0272 (13)	0.0262 (13)	0.0306 (14)	0.0038 (10)	0.0011 (10)	0.0026 (11)
C7	0.0357 (15)	0.0266 (14)	0.0292 (14)	−0.0003 (11)	−0.0012 (11)	0.0032 (11)
C8	0.0260 (13)	0.0267 (13)	0.0324 (14)	−0.0014 (10)	−0.0023 (11)	0.0096 (11)
C9	0.0229 (13)	0.0280 (14)	0.0366 (15)	0.0022 (10)	0.0022 (11)	0.0064 (11)
C10	0.0282 (13)	0.0275 (13)	0.0301 (14)	0.0022 (10)	0.0033 (11)	0.0025 (11)
C11	0.0304 (14)	0.0348 (15)	0.0393 (16)	−0.0022 (12)	0.0007 (13)	0.0072 (13)
C12	0.0249 (12)	0.0219 (12)	0.0216 (12)	−0.0018 (10)	0.0032 (10)	0.0007 (10)
C13	0.0218 (13)	0.0261 (13)	0.0342 (14)	−0.0021 (10)	0.0027 (11)	−0.0006 (11)
C14	0.038 (2)	0.0211 (18)	0.032 (2)	0.000	−0.0003 (16)	0.000
C15	0.0375 (15)	0.0310 (15)	0.0292 (14)	0.0076 (12)	−0.0038 (12)	−0.0051 (12)

S1—C4	1.724 (3)	C6—H6	0.9500
S1—C1	1.732 (3)	C7—C8	1.392 (4)
F1—C13	1.363 (3)	C7—H7	0.9500
F2—C13	1.341 (3)	C8—C9	1.390 (4)
F3—C14	1.331 (3)	C8—C11	1.446 (4)
N1—C11	1.144 (4)	C9—C10	1.384 (4)
C1—C2	1.367 (4)	C9—H9	0.9500
C1—C5	1.465 (3)	C10—H10	0.9500
C2—C3	1.427 (4)	C12—C12i	1.354 (5)
C2—H2	0.9500	C12—C13	1.502 (3)
C3—C4	1.380 (4)	C13—C14	1.531 (3)
C3—C12	1.467 (3)	C14—F3i	1.331 (3)
C4—C15	1.493 (4)	C14—C13i	1.531 (3)
C5—C6	1.389 (4)	C15—H15A	0.9800
C5—C10	1.402 (4)	C15—H15B	0.9800
C6—C7	1.380 (4)	C15—H15C	0.9800
C4—S1—C1	93.15 (13)	C8—C9—H9	120.3
C2—C1—C5	127.3 (2)	C9—C10—C5	120.8 (3)
C2—C1—S1	110.0 (2)	C9—C10—H10	119.6
C5—C1—S1	122.54 (19)	C5—C10—H10	119.6
C1—C2—C3	113.8 (2)	N1—C11—C8	177.0 (3)
C1—C2—H2	123.1	C12i—C12—C3	131.76 (14)
C3—C2—H2	123.1	C12i—C12—C13	110.66 (14)
C4—C3—C2	112.6 (2)	C3—C12—C13	117.6 (2)
C4—C3—C12	125.3 (2)	F2—C13—F1	104.8 (2)
C2—C3—C12	121.7 (2)	F2—C13—C12	113.5 (2)
C3—C4—C15	130.6 (2)	F1—C13—C12	111.3 (2)
C3—C4—S1	110.39 (19)	F2—C13—C14	112.1 (2)
C15—C4—S1	118.9 (2)	F1—C13—C14	108.70 (19)
C6—C5—C10	118.7 (2)	C12—C13—C14	106.5 (2)
C6—C5—C1	119.6 (2)	F3i—C14—F3	108.2 (4)
C10—C5—C1	121.6 (2)	F3i—C14—C13i	111.45 (14)
C7—C6—C5	120.9 (2)	F3—C14—C13i	110.49 (15)
C7—C6—H6	119.5	F3i—C14—C13	110.49 (15)
C5—C6—H6	119.5	F3—C14—C13	111.45 (14)
C6—C7—C8	119.8 (3)	C13i—C14—C13	104.8 (3)
C6—C7—H7	120.1	C4—C15—H15A	109.5
C8—C7—H7	120.1	C4—C15—H15B	109.5
C9—C8—C7	120.3 (2)	H15A—C15—H15B	109.5
C9—C8—C11	120.5 (2)	C4—C15—H15C	109.5
C7—C8—C11	119.2 (3)	H15A—C15—H15C	109.5
C10—C9—C8	119.4 (2)	H15B—C15—H15C	109.5
C10—C9—H9	120.3
C4—S1—C1—C2	0.4 (2)	C8—C9—C10—C5	1.1 (4)
C4—S1—C1—C5	−176.3 (2)	C6—C5—C10—C9	−1.2 (4)
C5—C1—C2—C3	176.4 (2)	C1—C5—C10—C9	175.4 (2)
S1—C1—C2—C3	−0.1 (3)	C4—C3—C12—C12i	37.9 (5)
C1—C2—C3—C4	−0.3 (3)	C2—C3—C12—C12i	−149.8 (3)
C1—C2—C3—C12	−173.6 (2)	C4—C3—C12—C13	−140.0 (3)
C2—C3—C4—C15	−176.1 (3)	C2—C3—C12—C13	32.3 (3)
C12—C3—C4—C15	−3.2 (5)	C12i—C12—C13—F2	−131.7 (3)
C2—C3—C4—S1	0.6 (3)	C3—C12—C13—F2	46.7 (3)
C12—C3—C4—S1	173.5 (2)	C12i—C12—C13—F1	110.5 (3)
C1—S1—C4—C3	−0.6 (2)	C3—C12—C13—F1	−71.2 (3)
C1—S1—C4—C15	176.6 (2)	C12i—C12—C13—C14	−7.9 (3)
C2—C1—C5—C6	21.9 (4)	C3—C12—C13—C14	170.46 (19)
S1—C1—C5—C6	−162.0 (2)	F2—C13—C14—F3i	7.2 (3)
C2—C1—C5—C10	−154.7 (3)	F1—C13—C14—F3i	122.5 (2)
S1—C1—C5—C10	21.4 (3)	C12—C13—C14—F3i	−117.5 (3)
C10—C5—C6—C7	0.6 (4)	F2—C13—C14—F3	−113.2 (3)
C1—C5—C6—C7	−176.0 (2)	F1—C13—C14—F3	2.2 (3)
C5—C6—C7—C8	0.0 (4)	C12—C13—C14—F3	122.2 (3)
C6—C7—C8—C9	−0.1 (4)	F2—C13—C14—C13i	127.3 (3)
C6—C7—C8—C11	−179.4 (3)	F1—C13—C14—C13i	−117.3 (2)
C7—C8—C9—C10	−0.4 (4)	C12—C13—C14—C13i	2.69 (11)
C11—C8—C9—C10	178.9 (2)