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The title compound, C23H15F6NS2 is a new non-symmetric photochromic dithienylethene. The mol­ecule adopts a photoactive anti­parallel conformation, the distance between the two reactive C atoms being 3.552 (6) Å. The dihedral angles between the cyclo­pentene ring and the two thio­phene rings are 44.0 (5) and 45.8 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048203/ob2096sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048203/ob2096Isup2.hkl
Contains datablock I

CCDC reference: 615594

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.044
  • wR factor = 0.140
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.731 1.000 Tmin(prime) and Tmax expected: 0.946 0.965 RR(prime) = 0.745 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.74
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C21 - C23 ... 1.43 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 121 C20 -C21 -C23 -N1 10.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 122 C22 -C21 -C23 -N1 8.00 0.00 1.555 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.50 Deg. F2 -C8 -F2' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.30 Deg. F1' -C8 -F1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 44.60 Deg. F3 -C9 -F3' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.90 Deg. F6 -C10 -F6' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 33.30 Deg. F5' -C10 -F5 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1-(2,5-Dimethyl-3-thienyl)-2-[2-methyl-5-(3-cyanophenyl)-3-thienyl]- 3,3,4,4,5,5-hexafluorocyclopent-1-ene top
Crystal data top
C23H15F6NS2Dx = 1.443 Mg m3
Mr = 483.48Melting point: 411.8 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.598 (4) ÅCell parameters from 2368 reflections
b = 8.7178 (18) Åθ = 2.7–22.4°
c = 17.250 (4) ŵ = 0.30 mm1
β = 116.899 (4)°T = 294 K
V = 2226.1 (8) Å3Block, colourless
Z = 40.18 × 0.14 × 0.12 mm
F(000) = 984
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
3935 independent reflections
Radiation source: fine-focus sealed tube2197 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1819
Tmin = 0.731, Tmax = 1.000k = 910
10978 measured reflectionsl = 1920
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0681P)2 + 0.2736P]
where P = (Fo2 + 2Fc2)/3
3935 reflections(Δ/σ)max = 0.002
346 parametersΔρmax = 0.28 e Å3
84 restraintsΔρmin = 0.26 e Å3
Special details top

Experimental. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 1.90 (s, 3H, –CH3), 1.99 (s, 3H, –CH3), 2.45 (s, 3H, –CH3), 6.75 (s, 1H, thiophene-H), 7.31 (s, 1H, thiophene-H), 7.51–7.53 (t, 1H, J = 4.0 Hz, benz-H), 7.58–7.60 (d, 1H, J = 8.0 Hz, benz-H), 7.76–7.78 (d, 1H, J = 8.0 Hz, benz-H), 7.81 (s, 1H, benz-H); 13C NMR (400 MHz, CDCl3, δ, p.p.m.): 14.2, 14.4, 15.0, 110.5, 116.1, 118.3, 124.2, 124.6, 126.2, 127.5, 128.0, 129.5, 132.9, 134.2, 136.7, 137.1, 137.5, 137.9, 140.1, 143.4.

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)
S10.30949 (8)0.95884 (11)0.75143 (7)0.0626 (3)
S20.29091 (6)0.96206 (11)1.08370 (6)0.0503 (3)
F10.4284 (5)0.4073 (12)0.9107 (5)0.079 (2)0.60
F20.3128 (5)0.3992 (11)0.7847 (4)0.079 (2)0.60
F30.3359 (5)0.1905 (5)0.9375 (4)0.0853 (17)0.60
F40.2093 (3)0.2852 (5)0.8462 (3)0.0839 (14)0.60
F50.3560 (4)0.3907 (8)1.0566 (3)0.0747 (17)0.60
F60.2116 (5)0.3875 (9)0.9889 (4)0.078 (2)0.60
F1'0.4149 (7)0.3906 (19)0.8732 (8)0.082 (4)0.40
F2'0.2709 (7)0.3939 (17)0.7844 (6)0.091 (4)0.40
F3'0.3884 (6)0.2611 (12)0.9858 (6)0.112 (3)0.40
F4'0.2636 (9)0.1978 (12)0.8927 (8)0.122 (3)0.40
F5'0.3102 (8)0.3926 (14)1.0595 (6)0.099 (3)0.40
F6'0.1880 (6)0.4011 (14)0.9422 (7)0.087 (3)0.40
N10.0263 (3)1.3705 (6)1.1528 (3)0.1277 (19)
C10.4706 (3)0.8942 (5)0.7406 (3)0.0803 (14)
H1A0.52260.82860.76650.120*
H1B0.48880.99880.75610.120*
H1C0.44320.88350.67850.120*
C20.4036 (3)0.8497 (4)0.7732 (2)0.0558 (10)
C30.4055 (2)0.7260 (4)0.8211 (2)0.0504 (9)
H30.45120.65300.83940.060*
C40.3311 (2)0.7171 (4)0.8409 (2)0.0422 (8)
C50.2724 (2)0.8371 (4)0.8072 (2)0.0464 (9)
C60.1865 (2)0.8713 (4)0.8121 (2)0.0607 (11)
H6A0.15530.77720.80930.091*
H6B0.14900.93610.76440.091*
H6C0.20020.92250.86600.091*
C70.3185 (2)0.5879 (4)0.8894 (2)0.0418 (8)
C80.3352 (3)0.4276 (4)0.8683 (2)0.0562 (10)
C90.3005 (3)0.3243 (4)0.9153 (3)0.0776 (14)
C100.2816 (3)0.4239 (4)0.9764 (3)0.0576 (10)
C110.2921 (2)0.5856 (4)0.9526 (2)0.0399 (8)
C120.2764 (2)0.7139 (4)0.9998 (2)0.0384 (8)
C130.3326 (2)0.8375 (4)1.0327 (2)0.0407 (8)
C140.4205 (2)0.8734 (4)1.0327 (2)0.0539 (10)
H14A0.45020.77961.03160.081*
H14B0.45800.93011.08420.081*
H14C0.40970.93350.98230.081*
C150.2002 (2)0.7213 (4)1.0170 (2)0.0442 (9)
H150.15620.64530.99960.053*
C160.1976 (2)0.8484 (4)1.0607 (2)0.0443 (9)
C170.1290 (2)0.8932 (4)1.0887 (2)0.0489 (9)
C180.0753 (3)0.7815 (5)1.1007 (3)0.0659 (11)
H180.08290.67881.09080.079*
C190.0111 (3)0.8223 (6)1.1271 (3)0.0827 (14)
H190.02470.74711.13430.099*
C200.0003 (3)0.9729 (7)1.1426 (3)0.0801 (14)
H200.04270.99931.16160.096*
C210.0510 (3)1.0851 (5)1.1302 (3)0.0693 (12)
C220.1158 (2)1.0459 (5)1.1033 (2)0.0585 (10)
H220.15041.12221.09520.070*
C230.0379 (3)1.2432 (7)1.1439 (3)0.0931 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0846 (8)0.0529 (6)0.0557 (7)0.0025 (5)0.0366 (6)0.0090 (5)
S20.0501 (6)0.0515 (6)0.0550 (6)0.0015 (4)0.0289 (5)0.0099 (5)
F10.086 (4)0.067 (4)0.105 (5)0.041 (3)0.061 (3)0.011 (4)
F20.131 (5)0.059 (3)0.077 (4)0.008 (4)0.072 (4)0.012 (2)
F30.140 (5)0.029 (2)0.098 (4)0.010 (3)0.064 (4)0.003 (2)
F40.094 (3)0.068 (3)0.081 (3)0.025 (3)0.032 (3)0.016 (2)
F50.095 (4)0.061 (3)0.061 (3)0.008 (3)0.029 (3)0.021 (2)
F60.109 (5)0.056 (3)0.108 (5)0.005 (3)0.083 (4)0.007 (4)
F1'0.105 (7)0.067 (5)0.118 (8)0.028 (5)0.089 (6)0.003 (6)
F2'0.123 (8)0.071 (5)0.056 (5)0.017 (6)0.020 (5)0.020 (4)
F3'0.126 (6)0.115 (6)0.120 (6)0.065 (5)0.078 (5)0.051 (5)
F4'0.154 (8)0.101 (7)0.135 (8)0.053 (6)0.086 (6)0.053 (6)
F5'0.156 (9)0.073 (5)0.080 (5)0.009 (7)0.064 (6)0.010 (4)
F6'0.085 (6)0.063 (5)0.136 (8)0.024 (4)0.072 (6)0.007 (6)
N10.081 (3)0.129 (4)0.158 (4)0.009 (3)0.040 (3)0.072 (4)
C10.093 (3)0.096 (3)0.072 (3)0.032 (3)0.055 (3)0.012 (3)
C20.065 (3)0.063 (3)0.048 (2)0.017 (2)0.033 (2)0.013 (2)
C30.053 (2)0.056 (2)0.051 (2)0.0041 (18)0.0307 (19)0.0024 (19)
C40.049 (2)0.042 (2)0.040 (2)0.0035 (17)0.0238 (17)0.0041 (16)
C50.055 (2)0.046 (2)0.041 (2)0.0064 (18)0.0241 (18)0.0013 (17)
C60.057 (3)0.066 (3)0.060 (2)0.020 (2)0.027 (2)0.012 (2)
C70.039 (2)0.040 (2)0.049 (2)0.0078 (15)0.0228 (17)0.0016 (17)
C80.067 (3)0.050 (2)0.058 (3)0.017 (2)0.033 (2)0.002 (2)
C90.115 (4)0.035 (2)0.106 (4)0.007 (3)0.070 (4)0.003 (3)
C100.071 (3)0.049 (2)0.060 (3)0.001 (2)0.036 (3)0.001 (2)
C110.039 (2)0.039 (2)0.045 (2)0.0028 (15)0.0217 (17)0.0020 (16)
C120.043 (2)0.0373 (19)0.0388 (19)0.0050 (16)0.0217 (16)0.0030 (15)
C130.042 (2)0.042 (2)0.042 (2)0.0081 (16)0.0222 (17)0.0040 (16)
C140.047 (2)0.054 (2)0.065 (2)0.0015 (18)0.029 (2)0.0092 (19)
C150.047 (2)0.046 (2)0.047 (2)0.0016 (16)0.0276 (18)0.0000 (17)
C160.044 (2)0.052 (2)0.041 (2)0.0084 (16)0.0226 (17)0.0044 (17)
C170.045 (2)0.066 (2)0.042 (2)0.0097 (19)0.0244 (18)0.0008 (19)
C180.068 (3)0.074 (3)0.073 (3)0.013 (2)0.047 (2)0.013 (2)
C190.069 (3)0.112 (4)0.091 (3)0.013 (3)0.057 (3)0.020 (3)
C200.061 (3)0.122 (4)0.073 (3)0.027 (3)0.044 (3)0.002 (3)
C210.047 (3)0.097 (4)0.058 (3)0.014 (2)0.019 (2)0.021 (2)
C220.046 (2)0.076 (3)0.054 (2)0.008 (2)0.023 (2)0.010 (2)
C230.057 (3)0.115 (4)0.096 (4)0.016 (3)0.025 (3)0.048 (3)
Geometric parameters (Å, º) top
S1—C21.720 (4)C6—H6B0.9600
S1—C51.723 (3)C6—H6C0.9600
S2—C161.727 (4)C7—C111.347 (4)
S2—C131.727 (3)C7—C81.502 (4)
F1—C81.390 (7)C8—C91.491 (5)
F2—C81.339 (7)C9—C101.504 (5)
F3—C91.284 (6)C10—C111.500 (5)
F4—C91.482 (6)C11—C121.475 (4)
F5—C101.405 (6)C12—C131.370 (4)
F6—C101.314 (6)C12—C151.424 (4)
F1'—C81.326 (9)C13—C141.491 (4)
F2'—C81.386 (9)C14—H14A0.9600
F3'—C91.518 (7)C14—H14B0.9600
F4'—C91.236 (7)C14—H14C0.9600
F5'—C101.318 (8)C15—C161.352 (4)
F6'—C101.405 (8)C15—H150.9300
N1—C231.149 (6)C16—C171.477 (4)
C1—C21.505 (5)C17—C221.391 (5)
C1—H1A0.9600C17—C181.397 (5)
C1—H1B0.9600C18—C191.383 (5)
C1—H1C0.9600C18—H180.9300
C2—C31.350 (5)C19—C201.370 (6)
C3—C41.424 (4)C19—H190.9300
C3—H30.9300C20—C211.375 (6)
C4—C51.368 (4)C20—H200.9300
C4—C71.473 (4)C21—C221.393 (5)
C5—C61.495 (5)C21—C231.431 (7)
C6—H6A0.9600C22—H220.9300
C2—S1—C593.25 (17)C8—C9—F3'100.8 (5)
C16—S2—C1392.69 (16)C10—C9—F3'94.4 (5)
C2—C1—H1A109.5F6—C10—F5'71.4 (6)
C2—C1—H1B109.5F6—C10—F6'30.9 (4)
H1A—C1—H1B109.5F5'—C10—F6'102.3 (7)
C2—C1—H1C109.5F6—C10—F5103.7 (5)
H1A—C1—H1C109.5F5'—C10—F533.3 (5)
H1B—C1—H1C109.5F6'—C10—F5134.1 (6)
C3—C2—C1128.2 (4)F6—C10—C11119.5 (5)
C3—C2—S1110.0 (3)F5'—C10—C11117.6 (6)
C1—C2—S1121.8 (3)F6'—C10—C11105.1 (6)
C2—C3—C4114.1 (3)F5—C10—C11107.7 (4)
C2—C3—H3122.9F6—C10—C9117.1 (5)
C4—C3—H3122.9F5'—C10—C9123.8 (6)
C5—C4—C3112.6 (3)F6'—C10—C999.5 (6)
C5—C4—C7124.7 (3)F5—C10—C9101.7 (4)
C3—C4—C7122.7 (3)C11—C10—C9105.3 (3)
C4—C5—C6130.0 (3)C7—C11—C12129.7 (3)
C4—C5—S1110.0 (3)C7—C11—C10110.9 (3)
C6—C5—S1120.0 (3)C12—C11—C10119.4 (3)
C5—C6—H6A109.5C13—C12—C15112.4 (3)
C5—C6—H6B109.5C13—C12—C11124.6 (3)
H6A—C6—H6B109.5C15—C12—C11123.0 (3)
C5—C6—H6C109.5C12—C13—C14130.4 (3)
H6A—C6—H6C109.5C12—C13—S2110.5 (2)
H6B—C6—H6C109.5C14—C13—S2119.1 (3)
C11—C7—C4130.8 (3)C13—C14—H14A109.5
C11—C7—C8110.2 (3)C13—C14—H14B109.5
C4—C7—C8119.0 (3)H14A—C14—H14B109.5
F1'—C8—F278.9 (6)C13—C14—H14C109.5
F1'—C8—F2'106.8 (7)H14A—C14—H14C109.5
F2—C8—F2'29.5 (5)H14B—C14—H14C109.5
F1'—C8—F125.3 (6)C16—C15—C12114.1 (3)
F2—C8—F1104.1 (5)C16—C15—H15122.9
F2'—C8—F1132.1 (6)C12—C15—H15122.9
F1'—C8—C9116.0 (8)C15—C16—C17128.6 (3)
F2—C8—C9119.2 (5)C15—C16—S2110.3 (2)
F2'—C8—C997.8 (6)C17—C16—S2121.1 (3)
F1—C8—C9104.4 (5)C22—C17—C18118.5 (3)
F1'—C8—C7119.9 (8)C22—C17—C16121.4 (3)
F2—C8—C7116.2 (5)C18—C17—C16120.1 (3)
F2'—C8—C7108.1 (6)C19—C18—C17120.5 (4)
F1—C8—C7105.9 (5)C19—C18—H18119.7
C9—C8—C7105.7 (3)C17—C18—H18119.7
F4'—C9—F351.5 (6)C20—C19—C18120.4 (4)
F4'—C9—F450.2 (7)C20—C19—H19119.8
F3—C9—F4101.1 (5)C18—C19—H19119.8
F4'—C9—C8128.7 (6)C19—C20—C21120.1 (4)
F3—C9—C8118.3 (4)C19—C20—H20120.0
F4—C9—C8101.9 (4)C21—C20—H20120.0
F4'—C9—C10120.4 (6)C20—C21—C22120.2 (4)
F3—C9—C10121.8 (4)C20—C21—C23120.6 (4)
F4—C9—C10103.7 (4)C22—C21—C23119.2 (5)
C8—C9—C10106.7 (3)C17—C22—C21120.3 (4)
F4'—C9—F3'95.1 (8)C17—C22—H22119.9
F3—C9—F3'44.6 (4)C21—C22—H22119.9
F4—C9—F3'145.3 (6)N1—C23—C21178.3 (6)
C5—S1—C2—C30.0 (3)F4'—C9—C10—F6'41.4 (11)
C5—S1—C2—C1179.8 (3)F3—C9—C10—F6'102.3 (8)
C1—C2—C3—C4179.8 (3)F4—C9—C10—F6'10.3 (6)
S1—C2—C3—C40.0 (4)C8—C9—C10—F6'117.4 (6)
C2—C3—C4—C50.1 (4)F3'—C9—C10—F6'139.9 (7)
C2—C3—C4—C7177.4 (3)F4'—C9—C10—F597.7 (10)
C3—C4—C5—C6179.6 (3)F3—C9—C10—F536.7 (7)
C7—C4—C5—C62.2 (6)F4—C9—C10—F5149.4 (4)
C3—C4—C5—S10.0 (4)C8—C9—C10—F5103.5 (4)
C7—C4—C5—S1177.4 (3)F3'—C9—C10—F50.8 (6)
C2—S1—C5—C40.0 (3)F4'—C9—C10—C11150.0 (9)
C2—S1—C5—C6179.6 (3)F3—C9—C10—C11149.0 (6)
C5—C4—C7—C1144.3 (6)F4—C9—C10—C1198.4 (4)
C3—C4—C7—C11138.6 (4)C8—C9—C10—C118.8 (4)
C5—C4—C7—C8134.8 (3)F3'—C9—C10—C11111.5 (5)
C3—C4—C7—C842.3 (5)C4—C7—C11—C127.1 (6)
C11—C7—C8—F1'123.8 (7)C8—C7—C11—C12173.7 (3)
C4—C7—C8—F1'56.9 (8)C4—C7—C11—C10175.1 (3)
C11—C7—C8—F2144.2 (5)C8—C7—C11—C104.1 (4)
C4—C7—C8—F235.1 (6)F6—C10—C11—C7137.3 (5)
C11—C7—C8—F2'113.5 (6)F5'—C10—C11—C7139.5 (7)
C4—C7—C8—F2'65.8 (7)F6'—C10—C11—C7107.6 (6)
C11—C7—C8—F1100.8 (5)F5—C10—C11—C7105.0 (4)
C4—C7—C8—F179.9 (5)C9—C10—C11—C73.0 (4)
C11—C7—C8—C99.6 (4)F6—C10—C11—C1244.7 (6)
C4—C7—C8—C9169.7 (3)F5'—C10—C11—C1238.5 (7)
F1'—C8—C9—F4'79.1 (13)F6'—C10—C11—C1274.4 (6)
F2—C8—C9—F4'12.4 (12)F5—C10—C11—C1273.1 (5)
F2'—C8—C9—F4'34.0 (12)C9—C10—C11—C12178.9 (3)
F1—C8—C9—F4'103.2 (11)C7—C11—C12—C1344.7 (5)
C7—C8—C9—F4'145.4 (10)C10—C11—C12—C13133.0 (3)
F1'—C8—C9—F317.4 (9)C7—C11—C12—C15136.0 (4)
F2—C8—C9—F374.1 (8)C10—C11—C12—C1546.3 (4)
F2'—C8—C9—F395.7 (8)C15—C12—C13—C14177.5 (3)
F1—C8—C9—F341.5 (7)C11—C12—C13—C141.9 (5)
C7—C8—C9—F3152.9 (5)C15—C12—C13—S20.4 (3)
F1'—C8—C9—F4127.1 (7)C11—C12—C13—S2179.8 (2)
F2—C8—C9—F435.7 (6)C16—S2—C13—C120.1 (3)
F2'—C8—C9—F414.1 (6)C16—S2—C13—C14178.3 (3)
F1—C8—C9—F4151.2 (5)C13—C12—C15—C160.9 (4)
C7—C8—C9—F497.3 (4)C11—C12—C15—C16179.7 (3)
F1'—C8—C9—C10124.5 (7)C12—C15—C16—C17179.8 (3)
F2—C8—C9—C10144.0 (5)C12—C15—C16—S21.0 (4)
F2'—C8—C9—C10122.4 (6)C13—S2—C16—C150.7 (3)
F1—C8—C9—C10100.4 (5)C13—S2—C16—C17179.9 (3)
C7—C8—C9—C1011.1 (4)C15—C16—C17—C22155.8 (4)
F1'—C8—C9—F3'26.4 (8)S2—C16—C17—C2225.1 (5)
F2—C8—C9—F3'117.9 (7)C15—C16—C17—C1823.9 (5)
F2'—C8—C9—F3'139.5 (7)S2—C16—C17—C18155.2 (3)
F1—C8—C9—F3'2.4 (6)C22—C17—C18—C190.4 (6)
C7—C8—C9—F3'109.1 (5)C16—C17—C18—C19179.9 (3)
F4'—C9—C10—F614.5 (11)C17—C18—C19—C200.6 (6)
F3—C9—C10—F675.5 (8)C18—C19—C20—C211.4 (7)
F4—C9—C10—F637.2 (6)C19—C20—C21—C221.2 (7)
C8—C9—C10—F6144.3 (5)C19—C20—C21—C23178.3 (4)
F3'—C9—C10—F6113.0 (6)C18—C17—C22—C210.7 (5)
F4'—C9—C10—F5'70.5 (12)C16—C17—C22—C21179.7 (3)
F3—C9—C10—F5'9.5 (10)C20—C21—C22—C170.1 (6)
F4—C9—C10—F5'122.1 (8)C23—C21—C22—C17179.3 (4)
C8—C9—C10—F5'130.7 (7)C20—C21—C23—N1101 (21)
F3'—C9—C10—F5'28.0 (9)C22—C21—C23—N178 (21)
 

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