2-[5-(3-Cyano­phen­yl)-2-methyl-3-thien­yl]-1-(2,5-dimethyl-3-thien­yl)-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-ene: a new photochromic diaryl­ethene compound

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)°.

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

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

Crystal data

C23H15F6NS2	Dx = 1.443 Mg m^−3
Mr = 483.48	Melting point: 411.8 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.598 (4) Å	Cell parameters from 2368 reflections
b = 8.7178 (18) Å	θ = 2.7–22.4°
c = 17.250 (4) Å	µ = 0.30 mm^−1
β = 116.899 (4)°	T = 294 K
V = 2226.1 (8) Å^3	Block, colourless
Z = 4	0.18 × 0.14 × 0.12 mm
F(000) = 984

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3935 independent reflections
Radiation source: fine-focus sealed tube	2197 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→19
Tmin = 0.731, Tmax = 1.000	k = −9→10
10978 measured reflections	l = −19→20

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0681P)^2 + 0.2736P] where P = (Fo^2 + 2Fc^2)/3
3935 reflections	(Δ/σ)max = 0.002
346 parameters	Δρmax = 0.28 e Å^−3
84 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.30949 (8)	0.95884 (11)	0.75143 (7)	0.0626 (3)
S2	0.29091 (6)	0.96206 (11)	1.08370 (6)	0.0503 (3)
F1	0.4284 (5)	0.4073 (12)	0.9107 (5)	0.079 (2)	0.60
F2	0.3128 (5)	0.3992 (11)	0.7847 (4)	0.079 (2)	0.60
F3	0.3359 (5)	0.1905 (5)	0.9375 (4)	0.0853 (17)	0.60
F4	0.2093 (3)	0.2852 (5)	0.8462 (3)	0.0839 (14)	0.60
F5	0.3560 (4)	0.3907 (8)	1.0566 (3)	0.0747 (17)	0.60
F6	0.2116 (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
N1	0.0263 (3)	1.3705 (6)	1.1528 (3)	0.1277 (19)
C1	0.4706 (3)	0.8942 (5)	0.7406 (3)	0.0803 (14)
H1A	0.5226	0.8286	0.7665	0.120*
H1B	0.4888	0.9988	0.7561	0.120*
H1C	0.4432	0.8835	0.6785	0.120*
C2	0.4036 (3)	0.8497 (4)	0.7732 (2)	0.0558 (10)
C3	0.4055 (2)	0.7260 (4)	0.8211 (2)	0.0504 (9)
H3	0.4512	0.6530	0.8394	0.060*
C4	0.3311 (2)	0.7171 (4)	0.8409 (2)	0.0422 (8)
C5	0.2724 (2)	0.8371 (4)	0.8072 (2)	0.0464 (9)
C6	0.1865 (2)	0.8713 (4)	0.8121 (2)	0.0607 (11)
H6A	0.1553	0.7772	0.8093	0.091*
H6B	0.1490	0.9361	0.7644	0.091*
H6C	0.2002	0.9225	0.8660	0.091*
C7	0.3185 (2)	0.5879 (4)	0.8894 (2)	0.0418 (8)
C8	0.3352 (3)	0.4276 (4)	0.8683 (2)	0.0562 (10)
C9	0.3005 (3)	0.3243 (4)	0.9153 (3)	0.0776 (14)
C10	0.2816 (3)	0.4239 (4)	0.9764 (3)	0.0576 (10)
C11	0.2921 (2)	0.5856 (4)	0.9526 (2)	0.0399 (8)
C12	0.2764 (2)	0.7139 (4)	0.9998 (2)	0.0384 (8)
C13	0.3326 (2)	0.8375 (4)	1.0327 (2)	0.0407 (8)
C14	0.4205 (2)	0.8734 (4)	1.0327 (2)	0.0539 (10)
H14A	0.4502	0.7796	1.0316	0.081*
H14B	0.4580	0.9301	1.0842	0.081*
H14C	0.4097	0.9335	0.9823	0.081*
C15	0.2002 (2)	0.7213 (4)	1.0170 (2)	0.0442 (9)
H15	0.1562	0.6453	0.9996	0.053*
C16	0.1976 (2)	0.8484 (4)	1.0607 (2)	0.0443 (9)
C17	0.1290 (2)	0.8932 (4)	1.0887 (2)	0.0489 (9)
C18	0.0753 (3)	0.7815 (5)	1.1007 (3)	0.0659 (11)
H18	0.0829	0.6788	1.0908	0.079*
C19	0.0111 (3)	0.8223 (6)	1.1271 (3)	0.0827 (14)
H19	−0.0247	0.7471	1.1343	0.099*
C20	−0.0003 (3)	0.9729 (7)	1.1426 (3)	0.0801 (14)
H20	−0.0427	0.9993	1.1616	0.096*
C21	0.0510 (3)	1.0851 (5)	1.1302 (3)	0.0693 (12)
C22	0.1158 (2)	1.0459 (5)	1.1033 (2)	0.0585 (10)
H22	0.1504	1.1222	1.0952	0.070*
C23	0.0379 (3)	1.2432 (7)	1.1439 (3)	0.0931 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0846 (8)	0.0529 (6)	0.0557 (7)	0.0025 (5)	0.0366 (6)	0.0090 (5)
S2	0.0501 (6)	0.0515 (6)	0.0550 (6)	0.0015 (4)	0.0289 (5)	−0.0099 (5)
F1	0.086 (4)	0.067 (4)	0.105 (5)	0.041 (3)	0.061 (3)	0.011 (4)
F2	0.131 (5)	0.059 (3)	0.077 (4)	0.008 (4)	0.072 (4)	−0.012 (2)
F3	0.140 (5)	0.029 (2)	0.098 (4)	0.010 (3)	0.064 (4)	0.003 (2)
F4	0.094 (3)	0.068 (3)	0.081 (3)	−0.025 (3)	0.032 (3)	−0.016 (2)
F5	0.095 (4)	0.061 (3)	0.061 (3)	0.008 (3)	0.029 (3)	0.021 (2)
F6	0.109 (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)
N1	0.081 (3)	0.129 (4)	0.158 (4)	0.009 (3)	0.040 (3)	−0.072 (4)
C1	0.093 (3)	0.096 (3)	0.072 (3)	−0.032 (3)	0.055 (3)	−0.012 (3)
C2	0.065 (3)	0.063 (3)	0.048 (2)	−0.017 (2)	0.033 (2)	−0.013 (2)
C3	0.053 (2)	0.056 (2)	0.051 (2)	0.0041 (18)	0.0307 (19)	−0.0024 (19)
C4	0.049 (2)	0.042 (2)	0.040 (2)	0.0035 (17)	0.0238 (17)	−0.0041 (16)
C5	0.055 (2)	0.046 (2)	0.041 (2)	0.0064 (18)	0.0241 (18)	0.0013 (17)
C6	0.057 (3)	0.066 (3)	0.060 (2)	0.020 (2)	0.027 (2)	0.012 (2)
C7	0.039 (2)	0.040 (2)	0.049 (2)	0.0078 (15)	0.0228 (17)	−0.0016 (17)
C8	0.067 (3)	0.050 (2)	0.058 (3)	0.017 (2)	0.033 (2)	0.002 (2)
C9	0.115 (4)	0.035 (2)	0.106 (4)	0.007 (3)	0.070 (4)	0.003 (3)
C10	0.071 (3)	0.049 (2)	0.060 (3)	−0.001 (2)	0.036 (3)	0.001 (2)
C11	0.039 (2)	0.039 (2)	0.045 (2)	0.0028 (15)	0.0217 (17)	0.0020 (16)
C12	0.043 (2)	0.0373 (19)	0.0388 (19)	0.0050 (16)	0.0217 (16)	0.0030 (15)
C13	0.042 (2)	0.042 (2)	0.042 (2)	0.0081 (16)	0.0222 (17)	0.0040 (16)
C14	0.047 (2)	0.054 (2)	0.065 (2)	−0.0015 (18)	0.029 (2)	−0.0092 (19)
C15	0.047 (2)	0.046 (2)	0.047 (2)	0.0016 (16)	0.0276 (18)	0.0000 (17)
C16	0.044 (2)	0.052 (2)	0.041 (2)	0.0084 (16)	0.0226 (17)	0.0044 (17)
C17	0.045 (2)	0.066 (2)	0.042 (2)	0.0097 (19)	0.0244 (18)	0.0008 (19)
C18	0.068 (3)	0.074 (3)	0.073 (3)	0.013 (2)	0.047 (2)	0.013 (2)
C19	0.069 (3)	0.112 (4)	0.091 (3)	0.013 (3)	0.057 (3)	0.020 (3)
C20	0.061 (3)	0.122 (4)	0.073 (3)	0.027 (3)	0.044 (3)	0.002 (3)
C21	0.047 (3)	0.097 (4)	0.058 (3)	0.014 (2)	0.019 (2)	−0.021 (2)
C22	0.046 (2)	0.076 (3)	0.054 (2)	0.008 (2)	0.023 (2)	−0.010 (2)
C23	0.057 (3)	0.115 (4)	0.096 (4)	0.016 (3)	0.025 (3)	−0.048 (3)

Geometric parameters (Å, º)

S1—C2	1.720 (4)	C6—H6B	0.9600
S1—C5	1.723 (3)	C6—H6C	0.9600
S2—C16	1.727 (4)	C7—C11	1.347 (4)
S2—C13	1.727 (3)	C7—C8	1.502 (4)
F1—C8	1.390 (7)	C8—C9	1.491 (5)
F2—C8	1.339 (7)	C9—C10	1.504 (5)
F3—C9	1.284 (6)	C10—C11	1.500 (5)
F4—C9	1.482 (6)	C11—C12	1.475 (4)
F5—C10	1.405 (6)	C12—C13	1.370 (4)
F6—C10	1.314 (6)	C12—C15	1.424 (4)
F1'—C8	1.326 (9)	C13—C14	1.491 (4)
F2'—C8	1.386 (9)	C14—H14A	0.9600
F3'—C9	1.518 (7)	C14—H14B	0.9600
F4'—C9	1.236 (7)	C14—H14C	0.9600
F5'—C10	1.318 (8)	C15—C16	1.352 (4)
F6'—C10	1.405 (8)	C15—H15	0.9300
N1—C23	1.149 (6)	C16—C17	1.477 (4)
C1—C2	1.505 (5)	C17—C22	1.391 (5)
C1—H1A	0.9600	C17—C18	1.397 (5)
C1—H1B	0.9600	C18—C19	1.383 (5)
C1—H1C	0.9600	C18—H18	0.9300
C2—C3	1.350 (5)	C19—C20	1.370 (6)
C3—C4	1.424 (4)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.375 (6)
C4—C5	1.368 (4)	C20—H20	0.9300
C4—C7	1.473 (4)	C21—C22	1.393 (5)
C5—C6	1.495 (5)	C21—C23	1.431 (7)
C6—H6A	0.9600	C22—H22	0.9300
C2—S1—C5	93.25 (17)	C8—C9—F3'	100.8 (5)
C16—S2—C13	92.69 (16)	C10—C9—F3'	94.4 (5)
C2—C1—H1A	109.5	F6—C10—F5'	71.4 (6)
C2—C1—H1B	109.5	F6—C10—F6'	30.9 (4)
H1A—C1—H1B	109.5	F5'—C10—F6'	102.3 (7)
C2—C1—H1C	109.5	F6—C10—F5	103.7 (5)
H1A—C1—H1C	109.5	F5'—C10—F5	33.3 (5)
H1B—C1—H1C	109.5	F6'—C10—F5	134.1 (6)
C3—C2—C1	128.2 (4)	F6—C10—C11	119.5 (5)
C3—C2—S1	110.0 (3)	F5'—C10—C11	117.6 (6)
C1—C2—S1	121.8 (3)	F6'—C10—C11	105.1 (6)
C2—C3—C4	114.1 (3)	F5—C10—C11	107.7 (4)
C2—C3—H3	122.9	F6—C10—C9	117.1 (5)
C4—C3—H3	122.9	F5'—C10—C9	123.8 (6)
C5—C4—C3	112.6 (3)	F6'—C10—C9	99.5 (6)
C5—C4—C7	124.7 (3)	F5—C10—C9	101.7 (4)
C3—C4—C7	122.7 (3)	C11—C10—C9	105.3 (3)
C4—C5—C6	130.0 (3)	C7—C11—C12	129.7 (3)
C4—C5—S1	110.0 (3)	C7—C11—C10	110.9 (3)
C6—C5—S1	120.0 (3)	C12—C11—C10	119.4 (3)
C5—C6—H6A	109.5	C13—C12—C15	112.4 (3)
C5—C6—H6B	109.5	C13—C12—C11	124.6 (3)
H6A—C6—H6B	109.5	C15—C12—C11	123.0 (3)
C5—C6—H6C	109.5	C12—C13—C14	130.4 (3)
H6A—C6—H6C	109.5	C12—C13—S2	110.5 (2)
H6B—C6—H6C	109.5	C14—C13—S2	119.1 (3)
C11—C7—C4	130.8 (3)	C13—C14—H14A	109.5
C11—C7—C8	110.2 (3)	C13—C14—H14B	109.5
C4—C7—C8	119.0 (3)	H14A—C14—H14B	109.5
F1'—C8—F2	78.9 (6)	C13—C14—H14C	109.5
F1'—C8—F2'	106.8 (7)	H14A—C14—H14C	109.5
F2—C8—F2'	29.5 (5)	H14B—C14—H14C	109.5
F1'—C8—F1	25.3 (6)	C16—C15—C12	114.1 (3)
F2—C8—F1	104.1 (5)	C16—C15—H15	122.9
F2'—C8—F1	132.1 (6)	C12—C15—H15	122.9
F1'—C8—C9	116.0 (8)	C15—C16—C17	128.6 (3)
F2—C8—C9	119.2 (5)	C15—C16—S2	110.3 (2)
F2'—C8—C9	97.8 (6)	C17—C16—S2	121.1 (3)
F1—C8—C9	104.4 (5)	C22—C17—C18	118.5 (3)
F1'—C8—C7	119.9 (8)	C22—C17—C16	121.4 (3)
F2—C8—C7	116.2 (5)	C18—C17—C16	120.1 (3)
F2'—C8—C7	108.1 (6)	C19—C18—C17	120.5 (4)
F1—C8—C7	105.9 (5)	C19—C18—H18	119.7
C9—C8—C7	105.7 (3)	C17—C18—H18	119.7
F4'—C9—F3	51.5 (6)	C20—C19—C18	120.4 (4)
F4'—C9—F4	50.2 (7)	C20—C19—H19	119.8
F3—C9—F4	101.1 (5)	C18—C19—H19	119.8
F4'—C9—C8	128.7 (6)	C19—C20—C21	120.1 (4)
F3—C9—C8	118.3 (4)	C19—C20—H20	120.0
F4—C9—C8	101.9 (4)	C21—C20—H20	120.0
F4'—C9—C10	120.4 (6)	C20—C21—C22	120.2 (4)
F3—C9—C10	121.8 (4)	C20—C21—C23	120.6 (4)
F4—C9—C10	103.7 (4)	C22—C21—C23	119.2 (5)
C8—C9—C10	106.7 (3)	C17—C22—C21	120.3 (4)
F4'—C9—F3'	95.1 (8)	C17—C22—H22	119.9
F3—C9—F3'	44.6 (4)	C21—C22—H22	119.9
F4—C9—F3'	145.3 (6)	N1—C23—C21	178.3 (6)
C5—S1—C2—C3	0.0 (3)	F4'—C9—C10—F6'	−41.4 (11)
C5—S1—C2—C1	179.8 (3)	F3—C9—C10—F6'	−102.3 (8)
C1—C2—C3—C4	−179.8 (3)	F4—C9—C10—F6'	10.3 (6)
S1—C2—C3—C4	0.0 (4)	C8—C9—C10—F6'	117.4 (6)
C2—C3—C4—C5	−0.1 (4)	F3'—C9—C10—F6'	−139.9 (7)
C2—C3—C4—C7	177.4 (3)	F4'—C9—C10—F5	97.7 (10)
C3—C4—C5—C6	179.6 (3)	F3—C9—C10—F5	36.7 (7)
C7—C4—C5—C6	2.2 (6)	F4—C9—C10—F5	149.4 (4)
C3—C4—C5—S1	0.0 (4)	C8—C9—C10—F5	−103.5 (4)
C7—C4—C5—S1	−177.4 (3)	F3'—C9—C10—F5	−0.8 (6)
C2—S1—C5—C4	0.0 (3)	F4'—C9—C10—C11	−150.0 (9)
C2—S1—C5—C6	−179.6 (3)	F3—C9—C10—C11	149.0 (6)
C5—C4—C7—C11	−44.3 (6)	F4—C9—C10—C11	−98.4 (4)
C3—C4—C7—C11	138.6 (4)	C8—C9—C10—C11	8.8 (4)
C5—C4—C7—C8	134.8 (3)	F3'—C9—C10—C11	111.5 (5)
C3—C4—C7—C8	−42.3 (5)	C4—C7—C11—C12	−7.1 (6)
C11—C7—C8—F1'	−123.8 (7)	C8—C7—C11—C12	173.7 (3)
C4—C7—C8—F1'	56.9 (8)	C4—C7—C11—C10	175.1 (3)
C11—C7—C8—F2	144.2 (5)	C8—C7—C11—C10	−4.1 (4)
C4—C7—C8—F2	−35.1 (6)	F6—C10—C11—C7	−137.3 (5)
C11—C7—C8—F2'	113.5 (6)	F5'—C10—C11—C7	139.5 (7)
C4—C7—C8—F2'	−65.8 (7)	F6'—C10—C11—C7	−107.6 (6)
C11—C7—C8—F1	−100.8 (5)	F5—C10—C11—C7	105.0 (4)
C4—C7—C8—F1	79.9 (5)	C9—C10—C11—C7	−3.0 (4)
C11—C7—C8—C9	9.6 (4)	F6—C10—C11—C12	44.7 (6)
C4—C7—C8—C9	−169.7 (3)	F5'—C10—C11—C12	−38.5 (7)
F1'—C8—C9—F4'	−79.1 (13)	F6'—C10—C11—C12	74.4 (6)
F2—C8—C9—F4'	12.4 (12)	F5—C10—C11—C12	−73.1 (5)
F2'—C8—C9—F4'	34.0 (12)	C9—C10—C11—C12	178.9 (3)
F1—C8—C9—F4'	−103.2 (11)	C7—C11—C12—C13	−44.7 (5)
C7—C8—C9—F4'	145.4 (10)	C10—C11—C12—C13	133.0 (3)
F1'—C8—C9—F3	−17.4 (9)	C7—C11—C12—C15	136.0 (4)
F2—C8—C9—F3	74.1 (8)	C10—C11—C12—C15	−46.3 (4)
F2'—C8—C9—F3	95.7 (8)	C15—C12—C13—C14	177.5 (3)
F1—C8—C9—F3	−41.5 (7)	C11—C12—C13—C14	−1.9 (5)
C7—C8—C9—F3	−152.9 (5)	C15—C12—C13—S2	−0.4 (3)
F1'—C8—C9—F4	−127.1 (7)	C11—C12—C13—S2	−179.8 (2)
F2—C8—C9—F4	−35.7 (6)	C16—S2—C13—C12	−0.1 (3)
F2'—C8—C9—F4	−14.1 (6)	C16—S2—C13—C14	−178.3 (3)
F1—C8—C9—F4	−151.2 (5)	C13—C12—C15—C16	0.9 (4)
C7—C8—C9—F4	97.3 (4)	C11—C12—C15—C16	−179.7 (3)
F1'—C8—C9—C10	124.5 (7)	C12—C15—C16—C17	179.8 (3)
F2—C8—C9—C10	−144.0 (5)	C12—C15—C16—S2	−1.0 (4)
F2'—C8—C9—C10	−122.4 (6)	C13—S2—C16—C15	0.7 (3)
F1—C8—C9—C10	100.4 (5)	C13—S2—C16—C17	179.9 (3)
C7—C8—C9—C10	−11.1 (4)	C15—C16—C17—C22	−155.8 (4)
F1'—C8—C9—F3'	26.4 (8)	S2—C16—C17—C22	25.1 (5)
F2—C8—C9—F3'	117.9 (7)	C15—C16—C17—C18	23.9 (5)
F2'—C8—C9—F3'	139.5 (7)	S2—C16—C17—C18	−155.2 (3)
F1—C8—C9—F3'	2.4 (6)	C22—C17—C18—C19	−0.4 (6)
C7—C8—C9—F3'	−109.1 (5)	C16—C17—C18—C19	179.9 (3)
F4'—C9—C10—F6	−14.5 (11)	C17—C18—C19—C20	−0.6 (6)
F3—C9—C10—F6	−75.5 (8)	C18—C19—C20—C21	1.4 (7)
F4—C9—C10—F6	37.2 (6)	C19—C20—C21—C22	−1.2 (7)
C8—C9—C10—F6	144.3 (5)	C19—C20—C21—C23	178.3 (4)
F3'—C9—C10—F6	−113.0 (6)	C18—C17—C22—C21	0.7 (5)
F4'—C9—C10—F5'	70.5 (12)	C16—C17—C22—C21	−179.7 (3)
F3—C9—C10—F5'	9.5 (10)	C20—C21—C22—C17	0.1 (6)
F4—C9—C10—F5'	122.1 (8)	C23—C21—C22—C17	−179.3 (4)
C8—C9—C10—F5'	−130.7 (7)	C20—C21—C23—N1	−101 (21)
F3'—C9—C10—F5'	−28.0 (9)	C22—C21—C23—N1	78 (21)