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The title compound, C29H16F12S2, a photochromic dithienyl­ethene, is a potential material for optical storage. It adopts a photo-active antiparallel conformation in the single crystalline phase. The distance between the two reactive C atoms is 3.624 (8) Å. The mol­ecule has crystallographic twofold rotation symmetry. The dihedral angles between the cyclo­pentene ring and the attached thio­phene and benzene rings are 47.2 (2) and 17.9 (2)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025134/hg6218sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025134/hg6218Isup2.hkl
Contains datablock I

CCDC reference: 264272

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.075
  • wR factor = 0.145
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C3
Author Response: The cyclopentene composed of C1, C2, C3, C1A and C2A is planar which is the average of two envelope conformations so that the displacement parameters of florine atoms of C2 and C3 are large. The displacement parameters of florine atoms of trifloromethyl are large because of the rotation of C10-C14 Single bond.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C14
Author Response: The cyclopentene composed of C1, C2, C3, C1A and C2A is planar which is the average of two envelope conformations so that the displacement parameters of florine atoms of C2 and C3 are large. The displacement parameters of florine atoms of trifloromethyl are large because of the rotation of C10-C14 Single bond.

Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C2
Author Response: The cyclopentene composed of C1, C2, C3, C1A and C2A is planar which is the average of two envelope conformations so that the displacement parameters of florine atoms of C2 and C3 are large. The displacement parameters of florine atoms of trifloromethyl are large because of the rotation of C10-C14 Single bond.

Alert level C PLAT213_ALERT_2_C Atom F3 has ADP max/min Ratio ............. 3.70 prolat PLAT220_ALERT_2_C Large Non-Solvent F Ueq(max)/Ueq(min) ... 2.68 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for F4 - C14 .. 5.12 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 1 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.

3,3,4,4,5,5-Hexafluoro-1,2-bis{3-methyl-5-[3-(trifluoromethyl)phenyl}- 2-thienyl]cyclopent-1-ene top
Crystal data top
C29H16F12S2F(000) = 1320
Mr = 656.54Dx = 1.577 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 37 reflections
a = 20.011 (2) Åθ = 4.8–12.5°
b = 8.6936 (8) ŵ = 0.29 mm1
c = 16.3481 (16) ÅT = 295 K
β = 103.498 (8)°Prism, yellow
V = 2765.5 (5) Å30.5 × 0.4 × 0.4 mm
Z = 4
Data collection top
Bruker P4
diffractometer
1876 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω scansh = 123
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
k = 101
Tmin = 0.843, Tmax = 0.889l = 1918
2996 measured reflections3 standard reflections every 97 reflections
2422 independent reflections 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) = 0.145H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.001P)2 + 13P]
where P = (Fo2 + 2Fc2)/3
2422 reflections(Δ/σ)max = 0.001
196 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.48 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*/Ueq
S10.38674 (6)1.08574 (13)0.58465 (7)0.0694 (3)
F10.4928 (2)1.4229 (4)0.6099 (2)0.1144 (12)
F20.40109 (18)1.4168 (4)0.6513 (3)0.1323 (14)
F30.5443 (4)1.5833 (6)0.7316 (3)0.307 (6)
F40.2878 (2)0.3479 (5)0.4435 (4)0.179 (2)
F50.2978 (4)0.3801 (6)0.3227 (3)0.233 (3)
F60.3843 (2)0.3753 (4)0.4253 (3)0.1250 (12)
C10.4842 (2)1.2295 (4)0.7086 (2)0.0601 (10)
C20.4683 (3)1.3908 (5)0.6771 (3)0.0762 (13)
C30.50001.4928 (8)0.75000.122 (4)
C40.4670 (2)1.0995 (5)0.6516 (2)0.0595 (10)
C50.5084 (2)0.9765 (5)0.6420 (2)0.0587 (10)
C60.4728 (2)0.8730 (5)0.5801 (3)0.0640 (11)
H6A0.49300.78420.56520.077*
C70.4068 (2)0.9134 (5)0.5443 (2)0.0612 (10)
C80.3548 (2)0.8310 (5)0.4808 (2)0.0624 (10)
C90.3626 (2)0.6754 (5)0.4659 (3)0.0675 (11)
H9A0.40130.62310.49570.081*
C100.3136 (2)0.5982 (6)0.4072 (3)0.0713 (12)
C110.2567 (3)0.6720 (7)0.3621 (3)0.0830 (14)
H11A0.22430.61930.32170.100*
C120.2478 (3)0.8249 (7)0.3770 (3)0.0878 (15)
H12A0.20860.87500.34700.105*
C130.2943 (2)0.9036 (6)0.4340 (3)0.0716 (12)
H13A0.28691.00720.44290.086*
C140.3219 (3)0.4310 (7)0.3949 (4)0.0998 (18)
C150.5817 (2)0.9549 (5)0.6877 (3)0.0737 (12)
H15A0.60221.05340.70400.110*
H15B0.60620.90420.65150.110*
H15C0.58370.89320.73690.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0706 (7)0.0580 (6)0.0748 (7)0.0121 (5)0.0072 (5)0.0026 (5)
F10.182 (3)0.0718 (19)0.098 (2)0.001 (2)0.049 (2)0.0193 (17)
F20.099 (2)0.072 (2)0.214 (4)0.0303 (18)0.012 (2)0.013 (2)
F30.520 (14)0.202 (5)0.130 (4)0.258 (7)0.064 (6)0.057 (4)
F40.148 (4)0.086 (3)0.316 (7)0.001 (3)0.083 (4)0.008 (4)
F50.397 (9)0.124 (4)0.115 (3)0.058 (4)0.069 (4)0.056 (3)
F60.119 (3)0.085 (2)0.169 (3)0.010 (2)0.029 (2)0.028 (2)
C10.063 (2)0.047 (2)0.073 (2)0.0028 (18)0.021 (2)0.0034 (18)
C20.092 (3)0.051 (3)0.085 (3)0.007 (2)0.022 (3)0.006 (2)
C30.214 (11)0.033 (3)0.106 (6)0.0000.012 (7)0.000
C40.065 (2)0.052 (2)0.061 (2)0.0025 (19)0.0157 (19)0.0020 (19)
C50.061 (2)0.055 (2)0.061 (2)0.0027 (19)0.0164 (19)0.0027 (19)
C60.070 (3)0.055 (2)0.067 (2)0.007 (2)0.016 (2)0.004 (2)
C70.068 (3)0.055 (2)0.060 (2)0.005 (2)0.0138 (19)0.0026 (19)
C80.069 (3)0.064 (3)0.054 (2)0.002 (2)0.0145 (19)0.0009 (19)
C90.070 (3)0.069 (3)0.062 (2)0.006 (2)0.011 (2)0.002 (2)
C100.079 (3)0.071 (3)0.064 (3)0.000 (2)0.015 (2)0.006 (2)
C110.081 (3)0.096 (4)0.066 (3)0.004 (3)0.005 (2)0.007 (3)
C120.084 (3)0.095 (4)0.077 (3)0.016 (3)0.003 (3)0.010 (3)
C130.077 (3)0.067 (3)0.068 (3)0.012 (2)0.011 (2)0.005 (2)
C140.091 (4)0.080 (4)0.118 (5)0.004 (3)0.006 (4)0.025 (4)
C150.064 (3)0.067 (3)0.088 (3)0.006 (2)0.013 (2)0.007 (2)
Geometric parameters (Å, º) top
S1—C71.721 (4)C6—C71.360 (5)
S1—C41.724 (4)C6—H6A0.9300
F1—C21.334 (5)C7—C81.472 (6)
F2—C21.331 (6)C8—C91.390 (6)
F3—C31.272 (6)C8—C131.420 (6)
F4—C141.368 (8)C9—C101.376 (6)
F5—C141.247 (7)C9—H9A0.9300
F6—C141.324 (6)C10—C111.364 (6)
C1—C1i1.354 (8)C10—C141.482 (7)
C1—C41.454 (5)C11—C121.370 (7)
C1—C21.502 (6)C11—H11A0.9300
C2—C31.502 (6)C12—C131.341 (7)
C3—F3i1.272 (6)C12—H12A0.9300
C3—C2i1.502 (6)C13—H13A0.9300
C4—C51.384 (5)C15—H15A0.9600
C5—C61.415 (6)C15—H15B0.9600
C5—C151.495 (5)C15—H15C0.9600
C7—S1—C492.2 (2)C9—C8—C7120.5 (4)
C1i—C1—C4128.7 (2)C13—C8—C7122.5 (4)
C1i—C1—C2110.8 (2)C10—C9—C8120.4 (4)
C4—C1—C2120.5 (4)C10—C9—H9A119.8
F2—C2—F1104.0 (4)C8—C9—H9A119.8
F2—C2—C3111.1 (4)C11—C10—C9121.2 (5)
F1—C2—C3111.2 (4)C11—C10—C14119.6 (5)
F2—C2—C1112.6 (4)C9—C10—C14119.2 (5)
F1—C2—C1112.8 (4)C10—C11—C12119.1 (5)
C3—C2—C1105.2 (4)C10—C11—H11A120.4
F3—C3—F3i103.6 (9)C12—C11—H11A120.4
F3—C3—C2111.5 (3)C13—C12—C11121.3 (5)
F3i—C3—C2111.3 (4)C13—C12—H12A119.3
F3—C3—C2i111.3 (4)C11—C12—H12A119.3
F3i—C3—C2i111.5 (3)C12—C13—C8120.9 (5)
C2—C3—C2i107.7 (6)C12—C13—H13A119.5
C5—C4—C1128.0 (4)C8—C13—H13A119.5
C5—C4—S1111.6 (3)F5—C14—F6110.4 (6)
C1—C4—S1120.4 (3)F5—C14—F4103.1 (6)
C4—C5—C6111.0 (4)F6—C14—F498.2 (5)
C4—C5—C15125.7 (4)F5—C14—C10116.5 (6)
C6—C5—C15123.3 (4)F6—C14—C10115.7 (5)
C7—C6—C5114.8 (4)F4—C14—C10110.7 (5)
C7—C6—H6A122.6C5—C15—H15A109.5
C5—C6—H6A122.6C5—C15—H15B109.5
C6—C7—C8129.3 (4)H15A—C15—H15B109.5
C6—C7—S1110.4 (3)C5—C15—H15C109.5
C8—C7—S1120.3 (3)H15A—C15—H15C109.5
C9—C8—C13117.0 (4)H15B—C15—H15C109.5
Symmetry code: (i) x+1, y, z+3/2.
 

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