2-{4-[2-(2,5-Dimethyl-3-thien­yl)-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-en­yl]-5-methyl-2-thienylmethyl­ene}propane­dinitrile: a new photochromic diaryl­ethene compound

The title compound, C₂₀H₁₂F₆N₂S₂, is a new asymmetric photochromic diaryl­ethene which contains 3-thienyl substituents. The distance between the two reactive C atoms in the mol­ecule is 3.677 (8) Å. The dihedral angles between the central cyclo­pentene ring and the two thio­phene rings are 47.6 (2) and 49.2 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.079
• wR factor = 0.155
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C5

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.47
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C11    -   C12    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C11    -   C13    ...       1.42 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-{4-[2-(2,5-Dimethyl-3-thienyl)-3,3,4,4,5,5-hexafluorocyclopent-1-enyl]- 5-methyl-2-thienylmethylene}propanedinitrile

Crystal data

C20H12F6N2S2	F(000) = 928
Mr = 458.44	Dx = 1.468 Mg m^−3
Monoclinic, P21/n	Melting point: 402.5 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.6074 (15) Å	Cell parameters from 38 reflections
b = 8.4990 (11) Å	θ = 7.9–12.5°
c = 17.9494 (19) Å	µ = 0.32 mm^−1
β = 91.745 (9)°	T = 295 K
V = 2074.9 (4) Å^3	Prism, yellow
Z = 4	0.4 × 0.3 × 0.3 mm

Data collection

Bruker P4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 1.9°
Graphite monochromator	h = −16→1
ω scans	k = −1→10
5015 measured reflections	l = −21→21
3873 independent reflections	3 standard reflections every 97 reflections
2280 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 5P] where P = (Fo^2 + 2Fc^2)/3
3873 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 1.10 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.60503 (9)	0.06523 (17)	0.29149 (7)	0.0782 (4)
S2	0.78833 (10)	0.05079 (17)	0.59737 (8)	0.0832 (4)
F1	0.8712 (2)	0.6173 (4)	0.4724 (3)	0.1411 (16)
F2	0.7801 (4)	0.6256 (4)	0.5652 (2)	0.1504 (18)
F3	0.7460 (4)	0.8368 (5)	0.4315 (3)	0.1605 (19)
F4	0.6399 (4)	0.7511 (6)	0.4996 (3)	0.1637 (18)
F5	0.5687 (3)	0.6430 (4)	0.3823 (3)	0.162 (2)
F6	0.7049 (5)	0.6382 (5)	0.3284 (2)	0.182 (2)
N1	0.1842 (3)	0.0423 (7)	0.1983 (3)	0.1130 (18)
N2	0.4751 (5)	−0.1663 (9)	0.1769 (4)	0.179 (4)
C1	0.6778 (3)	0.4378 (6)	0.4158 (3)	0.0664 (12)
C2	0.7425 (3)	0.4318 (6)	0.4736 (3)	0.0674 (12)
C3	0.7785 (4)	0.5947 (6)	0.4929 (3)	0.0837 (15)
C4	0.7123 (5)	0.7028 (7)	0.4487 (4)	0.0981 (18)
C5	0.6593 (4)	0.6046 (7)	0.3929 (3)	0.0843 (15)
C6	0.6820 (3)	0.1861 (6)	0.3424 (2)	0.0689 (12)
C7	0.6311 (3)	0.3093 (6)	0.3724 (3)	0.0660 (12)
C8	0.5302 (3)	0.3056 (6)	0.3525 (3)	0.0743 (13)
H8A	0.4857	0.3814	0.3676	0.089*
C9	0.5037 (3)	0.1800 (6)	0.3088 (3)	0.0725 (13)
C10	0.4053 (3)	0.1551 (6)	0.2815 (3)	0.0773 (14)
H10A	0.3592	0.2258	0.2989	0.093*
C11	0.3693 (4)	0.0454 (7)	0.2346 (3)	0.0778 (14)
C12	0.2660 (4)	0.0446 (7)	0.2137 (3)	0.0858 (15)
C13	0.4271 (5)	−0.0745 (9)	0.2027 (4)	0.111 (2)
C14	0.7900 (3)	0.1523 (7)	0.3478 (3)	0.0849 (16)
H14A	0.8261	0.2483	0.3416	0.127*
H14B	0.8069	0.0790	0.3096	0.127*
H14C	0.8063	0.1081	0.3959	0.127*
C15	0.7194 (3)	0.1829 (6)	0.5461 (3)	0.0706 (12)
C16	0.7781 (3)	0.2961 (6)	0.5176 (3)	0.0667 (12)
C17	0.8795 (3)	0.2737 (6)	0.5388 (3)	0.0800 (15)
H17A	0.9292	0.3414	0.5245	0.096*
C18	0.8962 (4)	0.1453 (6)	0.5815 (3)	0.0799 (14)
C19	0.6102 (4)	0.1667 (7)	0.5419 (3)	0.1000 (19)
H19A	0.5807	0.2691	0.5389	0.150*
H19B	0.5885	0.1135	0.5856	0.150*
H19C	0.5912	0.1068	0.4984	0.150*
C20	0.9920 (4)	0.0820 (8)	0.6127 (4)	0.115 (2)
H20A	1.0387	0.1663	0.6180	0.173*
H20B	1.0168	0.0039	0.5796	0.173*
H20C	0.9817	0.0354	0.6606	0.173*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0688 (7)	0.0814 (9)	0.0837 (8)	0.0120 (7)	−0.0119 (6)	−0.0141 (7)
S2	0.0839 (9)	0.0753 (9)	0.0898 (9)	−0.0024 (7)	−0.0061 (7)	0.0131 (7)
F1	0.077 (2)	0.101 (3)	0.244 (5)	−0.024 (2)	−0.031 (3)	0.037 (3)
F2	0.264 (6)	0.081 (2)	0.103 (3)	−0.025 (3)	−0.043 (3)	−0.004 (2)
F3	0.191 (4)	0.101 (3)	0.184 (4)	−0.042 (3)	−0.084 (3)	0.057 (3)
F4	0.157 (4)	0.156 (4)	0.177 (4)	0.029 (3)	−0.018 (3)	−0.063 (3)
F5	0.098 (3)	0.084 (2)	0.299 (6)	0.025 (2)	−0.087 (3)	−0.031 (3)
F6	0.326 (7)	0.120 (3)	0.102 (3)	0.063 (4)	0.057 (4)	0.036 (3)
N1	0.078 (3)	0.141 (5)	0.119 (4)	−0.020 (3)	−0.027 (3)	0.000 (4)
N2	0.127 (5)	0.187 (7)	0.221 (8)	0.044 (5)	−0.055 (5)	−0.115 (6)
C1	0.057 (2)	0.069 (3)	0.073 (3)	0.007 (2)	−0.005 (2)	0.000 (2)
C2	0.058 (3)	0.071 (3)	0.072 (3)	−0.001 (2)	−0.009 (2)	0.002 (2)
C3	0.087 (4)	0.078 (4)	0.085 (4)	−0.015 (3)	−0.024 (3)	0.008 (3)
C4	0.098 (4)	0.072 (4)	0.122 (5)	−0.006 (3)	−0.019 (4)	0.009 (4)
C5	0.085 (4)	0.082 (4)	0.086 (4)	0.017 (3)	−0.013 (3)	0.000 (3)
C6	0.061 (3)	0.078 (3)	0.067 (3)	0.007 (2)	−0.009 (2)	0.000 (3)
C7	0.056 (3)	0.072 (3)	0.070 (3)	0.006 (2)	−0.009 (2)	−0.003 (2)
C8	0.057 (3)	0.081 (3)	0.084 (3)	0.012 (3)	−0.008 (2)	−0.012 (3)
C9	0.058 (3)	0.080 (3)	0.078 (3)	0.007 (2)	−0.010 (2)	−0.003 (3)
C10	0.063 (3)	0.084 (4)	0.084 (3)	0.002 (3)	−0.008 (2)	−0.002 (3)
C11	0.065 (3)	0.088 (4)	0.079 (3)	−0.001 (3)	−0.016 (2)	−0.001 (3)
C12	0.077 (3)	0.097 (4)	0.082 (3)	−0.011 (3)	−0.016 (3)	0.001 (3)
C13	0.089 (4)	0.119 (5)	0.123 (5)	0.015 (4)	−0.039 (4)	−0.041 (4)
C14	0.058 (3)	0.104 (4)	0.092 (4)	0.018 (3)	−0.007 (3)	−0.009 (3)
C15	0.065 (3)	0.073 (3)	0.074 (3)	−0.003 (3)	−0.003 (2)	0.000 (3)
C16	0.063 (3)	0.070 (3)	0.066 (3)	−0.001 (2)	−0.009 (2)	0.000 (2)
C17	0.066 (3)	0.080 (3)	0.093 (4)	−0.008 (3)	−0.020 (3)	0.014 (3)
C18	0.068 (3)	0.082 (4)	0.088 (4)	0.001 (3)	−0.017 (3)	0.007 (3)
C19	0.066 (3)	0.109 (5)	0.126 (5)	−0.006 (3)	0.009 (3)	0.022 (4)
C20	0.083 (4)	0.110 (5)	0.150 (6)	0.007 (4)	−0.031 (4)	0.034 (4)

Geometric parameters (Å, º)

S1—C6	1.711 (5)	C8—C9	1.365 (6)
S1—C9	1.725 (5)	C8—H8A	0.9300
S2—C18	1.705 (5)	C9—C10	1.428 (6)
S2—C15	1.713 (5)	C10—C11	1.339 (7)
F1—C3	1.339 (6)	C10—H10A	0.9300
F2—C3	1.323 (6)	C11—C13	1.418 (8)
F3—C4	1.269 (7)	C11—C12	1.444 (7)
F4—C4	1.424 (7)	C14—H14A	0.9600
F5—C5	1.284 (6)	C14—H14B	0.9600
F6—C5	1.361 (7)	C14—H14C	0.9600
N1—C12	1.139 (6)	C15—C16	1.361 (6)
N2—C13	1.127 (8)	C15—C19	1.491 (6)
C1—C2	1.341 (6)	C16—C17	1.432 (6)
C1—C7	1.474 (6)	C17—C18	1.349 (7)
C1—C5	1.495 (7)	C17—H17A	0.9300
C2—C16	1.471 (6)	C18—C20	1.503 (7)
C2—C3	1.505 (7)	C19—H19A	0.9600
C3—C4	1.498 (7)	C19—H19B	0.9600
C4—C5	1.476 (8)	C19—H19C	0.9600
C6—C7	1.374 (6)	C20—H20A	0.9600
C6—C14	1.498 (6)	C20—H20B	0.9600
C7—C8	1.409 (6)	C20—H20C	0.9600
C6—S1—C9	92.5 (2)	C11—C10—C9	129.8 (5)
C18—S2—C15	93.5 (2)	C11—C10—H10A	115.1
C2—C1—C7	130.0 (5)	C9—C10—H10A	115.1
C2—C1—C5	110.5 (4)	C10—C11—C13	123.9 (5)
C7—C1—C5	119.3 (4)	C10—C11—C12	120.0 (5)
C1—C2—C16	130.0 (5)	C13—C11—C12	116.1 (5)
C1—C2—C3	110.2 (4)	N1—C12—C11	178.8 (7)
C16—C2—C3	119.9 (4)	N2—C13—C11	177.9 (9)
F2—C3—F1	104.7 (5)	C6—C14—H14A	109.5
F2—C3—C4	112.9 (6)	C6—C14—H14B	109.5
F1—C3—C4	108.8 (5)	H14A—C14—H14B	109.5
F2—C3—C2	113.8 (5)	C6—C14—H14C	109.5
F1—C3—C2	111.8 (5)	H14A—C14—H14C	109.5
C4—C3—C2	104.8 (4)	H14B—C14—H14C	109.5
F3—C4—F4	99.2 (6)	C16—C15—C19	129.9 (5)
F3—C4—C5	121.0 (6)	C16—C15—S2	110.3 (3)
F4—C4—C5	105.4 (5)	C19—C15—S2	119.7 (4)
F3—C4—C3	117.6 (5)	C15—C16—C17	112.2 (4)
F4—C4—C3	104.7 (6)	C15—C16—C2	124.6 (4)
C5—C4—C3	106.7 (5)	C17—C16—C2	123.1 (4)
F5—C5—F6	106.4 (5)	C18—C17—C16	113.8 (5)
F5—C5—C4	113.8 (5)	C18—C17—H17A	123.1
F6—C5—C4	103.4 (5)	C16—C17—H17A	123.1
F5—C5—C1	115.8 (5)	C17—C18—C20	129.1 (5)
F6—C5—C1	110.9 (5)	C17—C18—S2	110.2 (4)
C4—C5—C1	105.9 (4)	C20—C18—S2	120.7 (4)
C7—C6—C14	128.7 (4)	C15—C19—H19A	109.5
C7—C6—S1	111.1 (3)	C15—C19—H19B	109.5
C14—C6—S1	120.2 (4)	H19A—C19—H19B	109.5
C6—C7—C8	112.5 (4)	C15—C19—H19C	109.5
C6—C7—C1	123.9 (4)	H19A—C19—H19C	109.5
C8—C7—C1	123.5 (4)	H19B—C19—H19C	109.5
C9—C8—C7	113.6 (4)	C18—C20—H20A	109.5
C9—C8—H8A	123.2	C18—C20—H20B	109.5
C7—C8—H8A	123.2	H20A—C20—H20B	109.5
C8—C9—C10	122.7 (5)	C18—C20—H20C	109.5
C8—C9—S1	110.3 (3)	H20A—C20—H20C	109.5
C10—C9—S1	126.9 (4)	H20B—C20—H20C	109.5
C7—C1—C2—C16	−8.4 (9)	C9—S1—C6—C14	−177.8 (4)
C5—C1—C2—C16	175.8 (5)	C14—C6—C7—C8	177.3 (5)
C7—C1—C2—C3	172.7 (5)	S1—C6—C7—C8	−1.1 (6)
C5—C1—C2—C3	−3.0 (6)	C14—C6—C7—C1	1.6 (8)
C1—C2—C3—F2	134.5 (5)	S1—C6—C7—C1	−176.8 (4)
C16—C2—C3—F2	−44.4 (7)	C2—C1—C7—C6	−49.6 (8)
C1—C2—C3—F1	−107.1 (5)	C5—C1—C7—C6	125.8 (5)
C16—C2—C3—F1	73.9 (6)	C2—C1—C7—C8	135.2 (6)
C1—C2—C3—C4	10.6 (6)	C5—C1—C7—C8	−49.4 (7)
C16—C2—C3—C4	−168.3 (5)	C6—C7—C8—C9	1.0 (7)
F2—C3—C4—F3	81.9 (8)	C1—C7—C8—C9	176.7 (5)
F1—C3—C4—F3	−33.9 (9)	C7—C8—C9—C10	−179.1 (5)
C2—C3—C4—F3	−153.7 (6)	C7—C8—C9—S1	−0.4 (6)
F2—C3—C4—F4	−27.0 (7)	C6—S1—C9—C8	−0.2 (4)
F1—C3—C4—F4	−142.8 (5)	C6—S1—C9—C10	178.4 (5)
C2—C3—C4—F4	97.5 (5)	C8—C9—C10—C11	174.9 (5)
F2—C3—C4—C5	−138.3 (6)	S1—C9—C10—C11	−3.6 (9)
F1—C3—C4—C5	105.9 (6)	C9—C10—C11—C13	1.0 (10)
C2—C3—C4—C5	−13.9 (7)	C9—C10—C11—C12	−179.0 (5)
F3—C4—C5—F5	−81.2 (9)	C18—S2—C15—C16	0.2 (4)
F4—C4—C5—F5	29.8 (7)	C18—S2—C15—C19	−176.7 (5)
C3—C4—C5—F5	140.7 (6)	C19—C15—C16—C17	175.9 (5)
F3—C4—C5—F6	33.8 (8)	S2—C15—C16—C17	−0.5 (6)
F4—C4—C5—F6	144.8 (5)	C19—C15—C16—C2	−0.7 (9)
C3—C4—C5—F6	−104.3 (6)	S2—C15—C16—C2	−177.1 (4)
F3—C4—C5—C1	150.5 (6)	C1—C2—C16—C15	−47.4 (8)
F4—C4—C5—C1	−98.5 (5)	C3—C2—C16—C15	131.3 (5)
C3—C4—C5—C1	12.4 (7)	C1—C2—C16—C17	136.4 (6)
C2—C1—C5—F5	−133.2 (5)	C3—C2—C16—C17	−44.9 (7)
C7—C1—C5—F5	50.6 (7)	C15—C16—C17—C18	0.8 (7)
C2—C1—C5—F6	105.5 (5)	C2—C16—C17—C18	177.4 (5)
C7—C1—C5—F6	−70.7 (6)	C16—C17—C18—C20	178.5 (6)
C2—C1—C5—C4	−6.0 (7)	C16—C17—C18—S2	−0.7 (6)
C7—C1—C5—C4	177.7 (5)	C15—S2—C18—C17	0.3 (4)
C9—S1—C6—C7	0.8 (4)	C15—S2—C18—C20	−178.9 (5)