Download citation
Download citation
link to html
The title compound, C17H12F6OS2, is a new nonsymmetric photochromic diaryl­ethene which contains 3-thienyl substituents. The distance between the two reactive C atoms in the mol­ecule is 3.550 (7) Å. The dihedral angles between the central cyclo­pentene ring and two thio­phene rings are 44.7 (3) and 43.6 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600674X/is6183sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680600674X/is6183Isup2.hkl
Contains datablock I

CCDC reference: 605102

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.008 Å
  • Disorder in main residue
  • R factor = 0.075
  • wR factor = 0.162
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT213_ALERT_2_B Atom F5 has ADP max/min Ratio ............. 4.10 prolat PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C4'
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT213_ALERT_2_C Atom F6 has ADP max/min Ratio ............. 3.50 prolat PLAT301_ALERT_3_C Main Residue Disorder ......................... 21.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT431_ALERT_2_C Short Inter HL..A Contact F6 .. O1 .. 2.76 Ang.
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 5 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 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

1-(2,5-Dimethyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-2-(5-formyl-2-methyl- 3-thienyl)cyclopent-1-ene top
Crystal data top
C17H12F6OS2F(000) = 832
Mr = 410.39Dx = 1.542 Mg m3
Monoclinic, P21/cMelting point: 382.2 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 17.1836 (15) ÅCell parameters from 47 reflections
b = 8.8408 (8) Åθ = 2.4–16.9°
c = 11.6536 (16) ŵ = 0.36 mm1
β = 93.342 (9)°T = 295 K
V = 1767.4 (3) Å3Prism, colourless
Z = 40.4 × 0.2 × 0.2 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.029
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.4°
Graphite monochromatorh = 2020
ω scansk = 101
4094 measured reflectionsl = 113
3107 independent reflections3 standard reflections every 97 reflections
1421 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.001P)2 + 5P]
where P = (Fo2 + 2Fc2)/3
3107 reflections(Δ/σ)max < 0.001
267 parametersΔρmax = 0.51 e Å3
18 restraintsΔρmin = 0.30 e Å3
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
xyzUiso*/UeqOcc. (<1)
S10.42007 (9)0.70882 (18)0.49186 (14)0.0755 (5)
S20.07985 (9)0.70498 (19)0.51493 (14)0.0780 (5)
O10.5225 (5)0.7470 (10)0.2911 (6)0.189 (3)
C10.2871 (3)0.3389 (6)0.4874 (5)0.0596 (14)
C20.2138 (3)0.3387 (6)0.5202 (5)0.0599 (14)
C30.1851 (4)0.1788 (7)0.5327 (5)0.0831 (19)
C40.2511 (13)0.0781 (11)0.5155 (12)0.101 (7)0.65
F10.1530 (5)0.1444 (8)0.6282 (7)0.114 (3)0.65
F20.1296 (4)0.1498 (7)0.4434 (7)0.104 (2)0.65
F30.2406 (4)0.0466 (7)0.4505 (8)0.117 (3)0.65
F40.2884 (4)0.0314 (9)0.6137 (7)0.119 (3)0.65
F50.3289 (7)0.1549 (11)0.3552 (8)0.186 (7)0.65
F60.3768 (5)0.1466 (12)0.5338 (13)0.218 (8)0.65
C4'0.253 (2)0.080 (2)0.4892 (18)0.066 (8)*0.35
F1'0.1891 (10)0.164 (2)0.6511 (9)0.127 (8)*0.35
F2'0.1101 (6)0.1525 (19)0.5164 (14)0.110 (5)*0.35
F3'0.2558 (10)0.0370 (19)0.5633 (15)0.119 (5)*0.35
F4'0.2136 (9)0.0281 (18)0.3944 (11)0.114 (5)*0.35
F5'0.2980 (10)0.163 (2)0.3464 (9)0.106 (6)*0.35
F6'0.3898 (6)0.156 (3)0.4768 (13)0.090 (4)*0.35
C50.3137 (4)0.1796 (7)0.4629 (6)0.085 (2)
C60.3516 (3)0.5863 (6)0.5419 (5)0.0605 (14)
C70.3412 (3)0.4657 (6)0.4699 (5)0.0567 (13)
C80.3899 (3)0.4721 (7)0.3746 (5)0.0669 (15)
H8A0.39060.39760.31830.080*
C90.4344 (3)0.5972 (7)0.3749 (5)0.0695 (16)
C100.4878 (4)0.6299 (8)0.2892 (7)0.095 (2)
H10A0.49570.55970.23150.114*
C110.3172 (4)0.6211 (7)0.6547 (5)0.0803 (18)
H11A0.30640.52820.69340.120*
H11B0.26970.67710.64090.120*
H11C0.35360.68000.70170.120*
C120.1486 (3)0.5855 (6)0.4656 (5)0.0627 (14)
C130.1609 (3)0.4653 (6)0.5384 (5)0.0626 (14)
C140.1135 (3)0.4723 (7)0.6353 (5)0.0697 (16)
H14A0.11490.40000.69340.084*
C150.0661 (3)0.5957 (7)0.6333 (5)0.0733 (17)
C160.0042 (4)0.6480 (10)0.7196 (5)0.113 (3)
H16A0.01980.61390.79570.170*
H16B0.04580.60570.69660.170*
H16C0.00070.75640.71910.170*
C170.1843 (4)0.6182 (7)0.3531 (5)0.0807 (18)
H17A0.19740.52480.31700.121*
H17B0.23060.67780.36700.121*
H17C0.14760.67300.30360.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0753 (10)0.0651 (10)0.0871 (11)0.0131 (8)0.0136 (8)0.0056 (8)
S20.0759 (10)0.0708 (10)0.0881 (11)0.0171 (9)0.0113 (8)0.0066 (9)
O10.204 (8)0.188 (7)0.184 (7)0.033 (6)0.081 (6)0.034 (6)
C10.064 (3)0.048 (3)0.067 (3)0.001 (3)0.014 (3)0.002 (3)
C20.065 (3)0.049 (3)0.067 (3)0.003 (3)0.015 (3)0.005 (3)
C30.069 (4)0.061 (4)0.120 (6)0.001 (3)0.007 (4)0.008 (4)
C40.142 (14)0.039 (6)0.126 (12)0.001 (7)0.056 (13)0.019 (7)
F10.119 (7)0.061 (4)0.173 (7)0.001 (4)0.101 (6)0.028 (4)
F20.091 (4)0.073 (4)0.145 (6)0.022 (3)0.024 (4)0.008 (4)
F30.110 (5)0.050 (3)0.195 (8)0.021 (3)0.038 (6)0.038 (4)
F40.109 (5)0.104 (5)0.144 (7)0.018 (5)0.001 (5)0.053 (5)
F50.254 (14)0.072 (5)0.255 (12)0.053 (7)0.210 (11)0.083 (6)
F60.093 (6)0.052 (4)0.50 (3)0.020 (5)0.074 (10)0.006 (12)
C50.071 (4)0.058 (4)0.125 (6)0.005 (3)0.001 (4)0.006 (4)
C60.061 (3)0.054 (3)0.067 (4)0.005 (3)0.011 (3)0.003 (3)
C70.049 (3)0.051 (3)0.071 (3)0.004 (2)0.009 (3)0.003 (3)
C80.058 (3)0.067 (4)0.078 (4)0.006 (3)0.019 (3)0.004 (3)
C90.063 (3)0.070 (4)0.077 (4)0.002 (3)0.020 (3)0.018 (3)
C100.091 (5)0.082 (5)0.115 (6)0.014 (4)0.030 (4)0.026 (4)
C110.091 (4)0.080 (4)0.072 (4)0.018 (4)0.020 (3)0.011 (3)
C120.058 (3)0.059 (3)0.072 (4)0.004 (3)0.011 (3)0.004 (3)
C130.063 (3)0.054 (3)0.073 (4)0.003 (3)0.017 (3)0.003 (3)
C140.065 (4)0.071 (4)0.074 (4)0.010 (3)0.020 (3)0.002 (3)
C150.059 (3)0.075 (4)0.087 (4)0.010 (3)0.012 (3)0.018 (3)
C160.081 (4)0.188 (9)0.075 (4)0.047 (5)0.031 (4)0.035 (5)
C170.093 (5)0.073 (4)0.077 (4)0.016 (4)0.018 (3)0.010 (3)
Geometric parameters (Å, º) top
S1—C91.712 (6)F5'—C51.376 (9)
S1—C61.725 (5)F6'—C51.326 (9)
S2—C151.712 (6)C6—C71.362 (7)
S2—C121.709 (5)C6—C111.504 (7)
O1—C101.194 (9)C7—C81.430 (7)
C1—C21.338 (6)C8—C91.345 (7)
C1—C71.478 (7)C8—H8A0.9300
C1—C51.513 (7)C9—C101.425 (8)
C2—C131.466 (7)C10—H10A0.9300
C2—C31.507 (7)C11—H11A0.9600
C3—F11.306 (7)C11—H11B0.9600
C3—F2'1.312 (9)C11—H11C0.9600
C3—F1'1.383 (10)C12—C131.368 (7)
C3—F21.393 (7)C12—C171.507 (7)
C3—C41.47 (2)C13—C141.432 (7)
C3—C4'1.57 (4)C14—C151.360 (8)
C4—F31.343 (9)C14—H14A0.9300
C4—F41.343 (9)C15—C161.576 (8)
C4—C51.55 (2)C16—H16A0.9600
F5—C51.315 (8)C16—H16B0.9600
F6—C51.357 (8)C16—H16C0.9600
C4'—F4'1.343 (10)C17—H17A0.9600
C4'—F3'1.343 (10)C17—H17B0.9600
C4'—C51.41 (3)C17—H17C0.9600
C9—S1—C692.3 (3)C11—C6—C1277.8 (3)
C15—S2—C1293.0 (3)S1—C6—C12126.6 (3)
C2—C1—C7130.6 (5)C6—C7—C8112.7 (5)
C2—C1—C5110.6 (5)C6—C7—C1124.7 (5)
C7—C1—C5118.8 (5)C8—C7—C1122.5 (5)
C1—C2—C13130.0 (5)C9—C8—C7112.9 (5)
C1—C2—C3110.4 (5)C9—C8—H8A123.6
C13—C2—C3119.6 (5)C7—C8—H8A123.6
F2'—C3—F1'96.9 (10)C8—C9—C10123.7 (6)
F1—C3—F2106.9 (7)C8—C9—S1111.6 (4)
F1—C3—C4110.1 (8)C10—C9—S1124.8 (5)
F2—C3—C4106.7 (7)O1—C10—C9120.2 (8)
F1—C3—C2117.2 (6)O1—C10—H10A119.9
F2'—C3—C2118.5 (9)C9—C10—H10A119.9
F1'—C3—C2100.9 (10)C6—C11—H11A109.5
F2—C3—C2108.3 (5)C6—C11—H11B109.5
C4—C3—C2107.2 (7)H11A—C11—H11B109.5
F2'—C3—C4'126.7 (11)C6—C11—H11C109.5
F1'—C3—C4'105.8 (11)H11A—C11—H11C109.5
C2—C3—C4'103.8 (10)H11B—C11—H11C109.5
F3—C4—F4105.7 (10)C13—C12—C17129.2 (5)
F3—C4—C3119.8 (13)C13—C12—S2110.8 (4)
F4—C4—C3113.8 (13)C17—C12—S2119.9 (4)
F3—C4—C5109.0 (14)C13—C12—C674.5 (3)
F4—C4—C5101.9 (12)C17—C12—C677.0 (3)
C3—C4—C5105.2 (7)S2—C12—C6127.1 (3)
F4'—C4'—F3'105.4 (16)C12—C13—C14112.4 (5)
F4'—C4'—C5112.1 (19)C12—C13—C2125.3 (5)
F3'—C4'—C5128 (2)C14—C13—C2122.2 (5)
F4'—C4'—C396 (2)C15—C14—C13112.9 (6)
F3'—C4'—C3103 (2)C15—C14—H14A123.6
C5—C4'—C3107.0 (15)C13—C14—H14A123.6
F6'—C5—C4'127.5 (16)C14—C15—C16130.6 (6)
F6'—C5—F5'103.8 (11)C14—C15—S2110.8 (4)
C4'—C5—F5'92.5 (12)C16—C15—S2118.6 (5)
F5—C5—F6110.4 (10)C15—C16—H16A109.5
F6'—C5—C1115.5 (12)C15—C16—H16B109.5
F5—C5—C1114.4 (7)H16A—C16—H16B109.5
C4'—C5—C1108.0 (15)C15—C16—H16C109.5
F5'—C5—C1103.9 (10)H16A—C16—H16C109.5
F6—C5—C1108.9 (7)H16B—C16—H16C109.5
F5—C5—C4117.4 (8)C12—C17—H17A109.5
F6—C5—C4100.5 (9)C12—C17—H17B109.5
C1—C5—C4103.9 (7)H17A—C17—H17B109.5
C7—C6—C11130.8 (5)C12—C17—H17C109.5
C7—C6—S1110.5 (4)H17A—C17—H17C109.5
C11—C6—S1118.5 (4)H17B—C17—H17C109.5
C7—C6—C1275.6 (3)
C7—C1—C2—C136.8 (10)F4—C4—C5—F5129.8 (10)
C5—C1—C2—C13171.4 (6)C3—C4—C5—F5111.2 (10)
C7—C1—C2—C3176.4 (6)C3—C4—C5—C4'97 (10)
C5—C1—C2—C35.5 (6)C3—C4—C5—F5'91.9 (11)
C1—C2—C3—F1130.0 (7)F3—C4—C5—F6101.4 (11)
C13—C2—C3—F152.8 (9)F4—C4—C5—F610.0 (12)
C1—C2—C3—F2'151.7 (10)C3—C4—C5—F6129.0 (9)
C13—C2—C3—F2'25.5 (11)F3—C4—C5—C1145.9 (10)
C1—C2—C3—F1'104.2 (10)F4—C4—C5—C1102.7 (10)
C13—C2—C3—F1'78.6 (10)C3—C4—C5—C116.3 (8)
C1—C2—C3—F2109.1 (6)C9—S1—C6—C70.2 (5)
C13—C2—C3—F268.0 (7)C9—S1—C6—C11176.9 (5)
C1—C2—C3—C45.6 (8)C9—S1—C6—C1287.2 (3)
C13—C2—C3—C4177.2 (6)C11—C6—C7—C8175.7 (6)
C1—C2—C3—C4'5.3 (8)S1—C6—C7—C80.8 (6)
C13—C2—C3—C4'171.9 (7)C12—C6—C7—C8124.9 (4)
F1—C3—C4—F394.9 (13)C11—C6—C7—C13.1 (10)
F2—C3—C4—F320.7 (15)S1—C6—C7—C1179.7 (4)
C2—C3—C4—F3136.5 (12)C12—C6—C7—C156.2 (5)
F1—C3—C4—F431.5 (13)C2—C1—C7—C643.3 (9)
F2—C3—C4—F4147.1 (9)C5—C1—C7—C6138.6 (6)
C2—C3—C4—F497.1 (11)C2—C1—C7—C8137.9 (6)
F1—C3—C4—C5142.2 (8)C5—C1—C7—C840.1 (8)
F2'—C3—C4—C5140.4 (12)C6—C7—C8—C91.3 (7)
F1'—C3—C4—C5116.7 (10)C1—C7—C8—C9179.9 (5)
F2—C3—C4—C5102.2 (7)C7—C8—C9—C10180.0 (6)
C2—C3—C4—C513.6 (8)C7—C8—C9—S11.1 (6)
F2'—C3—C4'—F4'30.4 (19)C6—S1—C9—C80.6 (5)
F1'—C3—C4'—F4'141.9 (14)C6—S1—C9—C10179.4 (6)
C2—C3—C4'—F4'112.3 (12)C8—C9—C10—O1175.8 (8)
F1—C3—C4'—F3'6.9 (18)S1—C9—C10—O15.4 (12)
F2'—C3—C4'—F3'76.9 (17)C15—S2—C12—C130.3 (5)
F1'—C3—C4'—F3'34.6 (18)C15—S2—C12—C17177.6 (5)
C2—C3—C4'—F3'140.5 (13)C15—S2—C12—C686.2 (3)
F1—C3—C4'—C5130.4 (10)C7—C6—C12—C1372.4 (4)
F2—C3—C4'—C5114.3 (9)C11—C6—C12—C1365.8 (4)
C2—C3—C4'—C53.1 (11)S1—C6—C12—C13177.5 (4)
F4'—C4'—C5—F6'111 (2)C7—C6—C12—C1765.2 (4)
F3'—C4'—C5—F6'22 (4)C11—C6—C12—C17156.6 (4)
C3—C4'—C5—F6'144.8 (13)S1—C6—C12—C1739.9 (5)
F4'—C4'—C5—F5'2 (2)C7—C6—C12—S2177.1 (4)
F3'—C4'—C5—F5'132 (3)C11—C6—C12—S238.8 (5)
C3—C4'—C5—F5'105.7 (12)S1—C6—C12—S277.8 (4)
F4'—C4'—C5—C1104 (2)C17—C12—C13—C14177.7 (6)
F3'—C4'—C5—C1123 (3)S2—C12—C13—C140.1 (7)
C3—C4'—C5—C10.2 (11)C6—C12—C13—C14124.2 (5)
C2—C1—C5—F6'153.0 (9)C17—C12—C13—C20.0 (10)
C7—C1—C5—F6'28.6 (11)S2—C12—C13—C2177.6 (5)
C2—C1—C5—F5115.7 (8)C6—C12—C13—C258.0 (5)
C7—C1—C5—F562.7 (9)C1—C2—C13—C1245.8 (9)
C2—C1—C5—C4'3.3 (9)C3—C2—C13—C12130.8 (6)
C7—C1—C5—C4'178.2 (8)C1—C2—C13—C14136.7 (6)
C2—C1—C5—F5'94.0 (10)C3—C2—C13—C1446.8 (8)
C7—C1—C5—F5'84.4 (10)C12—C13—C14—C150.6 (8)
C2—C1—C5—F6120.1 (9)C2—C13—C14—C15177.3 (5)
C7—C1—C5—F661.4 (10)C13—C14—C15—C16179.1 (6)
C2—C1—C5—C413.6 (7)C13—C14—C15—S20.8 (7)
C7—C1—C5—C4168.0 (6)C12—S2—C15—C140.6 (5)
C3—C4—C5—F6'151.0 (12)C12—S2—C15—C16179.2 (5)
F3—C4—C5—F518.4 (15)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds