3,3,4,4,5,5-Hexa-fluoro-1,2-bis[4-(phenyl-ethyn-yl)phen-yl]-cyclo-pentene.

The title compound, C(33)H(18)F(6), has a V-shaped conjugated subunit. The dihedral angles between the central cyclo-pentene ring and the directly attached benzene rings are 32.7 (2) and 53.7 (2)°, respectively. The fluoro substituents are disordered, the occupancies refined to a 0.675 (2):0.325 (2) ratio.

Related literature

The title compound was synthesised with the aim of simulating the characteristics of so-called left-handed materials on a mol­ecular scale. For a theoretical description of left-handed materials, see: Veselago (1968 ▶). For experimentally observed left-handed materials, see: Shelby et al. (2000 ▶); Chen et al. (2004 ▶); Zhou et al. (2006 ▶); Zhang et al. (2005 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

C33H18F6

M = 528.47

Monoclinic,

a = 16.350 (1) Å

b = 9.2893 (7) Å

c = 17.980 (1) Å

β = 103.654 (1)°

V = 2653.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.45 × 0.41 × 0.38 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.954, T max = 0.961

22979 measured reflections

6087 independent reflections

3767 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.01

6087 reflections

407 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052040/im2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052040/im2157Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C33H18F6	F(000) = 1080
Mr = 528.47	Dx = 1.323 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6530 reflections
a = 16.350 (1) Å	θ = 2.3–25.8°
b = 9.2893 (7) Å	µ = 0.11 mm−1
c = 17.980 (1) Å	T = 296 K
β = 103.654 (1)°	Block, yellow
V = 2653.6 (4) Å3	0.45 × 0.41 × 0.38 mm
Z = 4

Bruker APEXII CCD diffractometer	6087 independent reflections
Radiation source: fine-focus sealed tube	3767 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
Tmin = 0.954, Tmax = 0.961	k = −12→12
22979 measured reflections	l = −23→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0298P)2 + 0.8178P] where P = (Fo2 + 2Fc2)/3
6087 reflections	(Δ/σ)max = 0.002
407 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C26	0.19961 (9)	1.02109 (17)	1.03064 (9)	0.0496 (4)
C22	0.10730 (11)	0.6218 (2)	0.93186 (10)	0.0611 (4)
C23	0.13842 (10)	0.75808 (18)	0.96494 (9)	0.0557 (4)
C12	0.36369 (9)	1.19273 (17)	1.01487 (9)	0.0512 (4)
C7	0.55877 (11)	1.1281 (2)	0.81141 (10)	0.0687 (5)
C20	0.04809 (11)	0.37578 (18)	0.87084 (9)	0.0557 (4)
C11	0.33280 (10)	1.1354 (2)	0.94246 (9)	0.0628 (5)
H11	0.2761	1.1117	0.9268	0.075*
C9	0.46915 (10)	1.1503 (2)	0.91437 (10)	0.0623 (5)
C21	0.08196 (11)	0.5089 (2)	0.90495 (10)	0.0596 (4)
C27	0.24980 (10)	0.89899 (19)	1.04209 (10)	0.0587 (4)
H27	0.3046	0.9051	1.0717	0.070*
C28	0.21994 (11)	0.76934 (19)	1.01039 (10)	0.0618 (4)
H28	0.2544	0.6884	1.0193	0.074*
C8	0.52015 (11)	1.1357 (2)	0.85985 (10)	0.0690 (5)
C24	0.08860 (10)	0.88041 (19)	0.95314 (10)	0.0625 (5)
H24	0.0342	0.8748	0.9226	0.075*
C25	0.11797 (10)	1.01009 (19)	0.98572 (10)	0.0594 (4)
H25	0.0832	1.0906	0.9777	0.071*
C6	0.60588 (10)	1.1192 (2)	0.75391 (10)	0.0646 (5)
C14	0.50063 (11)	1.2050 (2)	0.98687 (11)	0.0707 (5)
H14	0.5575	1.2280	1.0024	0.085*
C13	0.44917 (10)	1.2260 (2)	1.03648 (10)	0.0647 (5)
H13	0.4718	1.2630	1.0851	0.078*
C15	−0.02972 (12)	0.3286 (2)	0.87935 (11)	0.0707 (5)
H15	−0.0586	0.3821	0.9086	0.085*
C19	0.09035 (14)	0.2938 (2)	0.82795 (11)	0.0771 (6)
H19	0.1431	0.3225	0.8226	0.093*
C10	0.38442 (11)	1.1131 (2)	0.89358 (10)	0.0689 (5)
H10	0.3624	1.0725	0.8458	0.083*
C1	0.58778 (14)	1.0158 (2)	0.69804 (13)	0.0854 (6)
H1	0.5440	0.9514	0.6972	0.102*
C16	−0.06433 (14)	0.2039 (3)	0.84499 (13)	0.0880 (6)
H16	−0.1163	0.1727	0.8513	0.106*
C17	−0.02255 (19)	0.1254 (3)	0.80152 (13)	0.0992 (8)
H17	−0.0466	0.0417	0.7776	0.119*
C4	0.71624 (17)	1.2032 (4)	0.69872 (17)	0.1292 (11)
H4	0.7600	1.2673	0.6989	0.155*
C18	0.05436 (19)	0.1691 (2)	0.79302 (13)	0.1001 (8)
H18	0.0827	0.1147	0.7636	0.120*
C2	0.63364 (18)	1.0065 (3)	0.64331 (15)	0.1086 (8)
H2	0.6204	0.9364	0.6054	0.130*
C5	0.67010 (15)	1.2145 (3)	0.75389 (14)	0.1059 (8)
H5	0.6825	1.2864	0.7908	0.127*
C3	0.69781 (18)	1.0985 (4)	0.64418 (16)	0.1128 (9)
H3	0.7294	1.0904	0.6076	0.135*
C29	0.23397 (9)	1.15683 (17)	1.06773 (9)	0.0498 (4)
C30	0.30656 (9)	1.22316 (17)	1.06528 (9)	0.0497 (4)
C31	0.32336 (11)	1.34507 (19)	1.12133 (10)	0.0607 (4)
C33	0.19144 (12)	1.2310 (2)	1.12173 (11)	0.0687 (5)
C32	0.24253 (12)	1.3637 (3)	1.14835 (12)	0.0749 (6)
F1	0.3864 (5)	1.3132 (8)	1.1850 (5)	0.0784 (12)	0.675 (12)
F2	0.3498 (3)	1.4682 (7)	1.0946 (4)	0.0804 (11)	0.675 (12)
F5	0.1123 (2)	1.2516 (6)	1.1010 (4)	0.0953 (16)	0.675 (12)
F3	0.1990 (2)	1.4774 (4)	1.1027 (3)	0.0916 (12)	0.675 (12)
F4	0.2516 (2)	1.4078 (6)	1.2183 (3)	0.0956 (15)	0.675 (12)
F6	0.2036 (5)	1.1456 (4)	1.1900 (3)	0.0992 (13)	0.675 (12)
F3'	0.2714 (6)	1.301 (2)	1.2310 (3)	0.139 (5)	0.325 (12)
F4'	0.2128 (5)	1.4715 (12)	1.1595 (14)	0.148 (7)	0.325 (12)
F2'	0.3905 (11)	1.328 (2)	1.1726 (11)	0.120 (6)	0.325 (12)
F1'	0.3278 (12)	1.4677 (15)	1.0822 (11)	0.136 (5)	0.325 (12)
F5'	0.1528 (8)	1.1542 (8)	1.1592 (6)	0.092 (3)	0.325 (12)
F6'	0.1151 (6)	1.3026 (12)	1.0670 (6)	0.093 (3)	0.325 (12)

	U11	U22	U33	U12	U13	U23
C26	0.0444 (8)	0.0530 (9)	0.0529 (9)	−0.0063 (7)	0.0145 (7)	0.0000 (7)
C22	0.0645 (10)	0.0591 (11)	0.0634 (11)	−0.0080 (9)	0.0224 (9)	−0.0028 (9)
C23	0.0567 (9)	0.0552 (10)	0.0585 (10)	−0.0098 (8)	0.0204 (8)	−0.0026 (8)
C12	0.0444 (8)	0.0555 (10)	0.0520 (9)	−0.0046 (7)	0.0082 (7)	0.0031 (8)
C7	0.0511 (9)	0.0925 (14)	0.0618 (11)	0.0041 (9)	0.0118 (9)	0.0063 (10)
C20	0.0668 (10)	0.0501 (9)	0.0509 (9)	−0.0051 (8)	0.0153 (8)	0.0017 (8)
C11	0.0453 (8)	0.0886 (13)	0.0534 (10)	−0.0120 (9)	0.0092 (7)	−0.0005 (9)
C9	0.0498 (9)	0.0783 (12)	0.0593 (10)	0.0031 (9)	0.0143 (8)	0.0063 (9)
C21	0.0644 (10)	0.0567 (11)	0.0602 (10)	−0.0057 (9)	0.0195 (8)	−0.0014 (9)
C27	0.0468 (9)	0.0619 (11)	0.0641 (10)	−0.0006 (8)	0.0066 (8)	−0.0017 (9)
C28	0.0605 (10)	0.0540 (10)	0.0703 (11)	0.0046 (8)	0.0142 (9)	0.0003 (9)
C8	0.0511 (9)	0.0932 (14)	0.0623 (11)	0.0046 (9)	0.0124 (9)	0.0069 (10)
C24	0.0453 (9)	0.0628 (11)	0.0758 (12)	−0.0087 (8)	0.0072 (8)	−0.0064 (9)
C25	0.0458 (9)	0.0555 (10)	0.0746 (11)	−0.0003 (8)	0.0094 (8)	−0.0026 (9)
C6	0.0513 (9)	0.0838 (13)	0.0604 (10)	0.0053 (9)	0.0163 (8)	0.0092 (10)
C14	0.0422 (8)	0.0988 (15)	0.0702 (12)	−0.0067 (9)	0.0113 (8)	−0.0038 (11)
C13	0.0472 (9)	0.0844 (13)	0.0604 (10)	−0.0097 (9)	0.0083 (8)	−0.0096 (9)
C15	0.0685 (11)	0.0666 (12)	0.0791 (13)	−0.0076 (10)	0.0218 (10)	−0.0046 (10)
C19	0.0946 (14)	0.0682 (13)	0.0806 (13)	−0.0088 (11)	0.0448 (12)	−0.0060 (11)
C10	0.0575 (10)	0.0963 (15)	0.0522 (10)	−0.0098 (10)	0.0117 (8)	−0.0062 (10)
C1	0.0902 (15)	0.0793 (14)	0.0971 (16)	−0.0048 (12)	0.0428 (13)	−0.0035 (13)
C16	0.0857 (14)	0.0859 (16)	0.0893 (15)	−0.0297 (12)	0.0142 (12)	−0.0059 (13)
C17	0.148 (2)	0.0765 (15)	0.0707 (14)	−0.0385 (16)	0.0214 (15)	−0.0146 (12)
C4	0.105 (2)	0.179 (3)	0.117 (2)	−0.048 (2)	0.0534 (18)	0.014 (2)
C18	0.159 (2)	0.0739 (15)	0.0832 (15)	−0.0110 (15)	0.0608 (16)	−0.0200 (12)
C2	0.138 (2)	0.0981 (18)	0.1097 (19)	0.0115 (17)	0.0701 (18)	−0.0086 (15)
C5	0.1026 (17)	0.132 (2)	0.0909 (16)	−0.0434 (16)	0.0391 (14)	−0.0131 (15)
C3	0.106 (2)	0.149 (3)	0.103 (2)	0.0215 (19)	0.0633 (17)	0.0258 (19)
C29	0.0447 (8)	0.0531 (9)	0.0512 (9)	−0.0019 (7)	0.0103 (7)	0.0012 (7)
C30	0.0443 (8)	0.0532 (9)	0.0486 (9)	−0.0021 (7)	0.0048 (7)	0.0020 (7)
C31	0.0520 (10)	0.0613 (11)	0.0656 (11)	−0.0086 (9)	0.0076 (9)	−0.0058 (9)
C33	0.0594 (11)	0.0736 (13)	0.0803 (13)	−0.0109 (10)	0.0304 (10)	−0.0131 (11)
C32	0.0639 (11)	0.0832 (15)	0.0783 (14)	−0.0063 (11)	0.0180 (10)	−0.0299 (12)
F1	0.059 (2)	0.105 (3)	0.0622 (17)	0.0063 (17)	−0.0038 (14)	−0.0136 (18)
F2	0.0774 (16)	0.063 (2)	0.107 (2)	−0.0201 (11)	0.0328 (14)	−0.0124 (16)
F5	0.0460 (12)	0.122 (3)	0.121 (4)	−0.0099 (17)	0.0250 (19)	−0.049 (3)
F3	0.0723 (13)	0.0717 (16)	0.131 (3)	0.0201 (11)	0.0252 (17)	0.0108 (17)
F4	0.0840 (19)	0.127 (4)	0.0782 (18)	−0.015 (2)	0.0248 (13)	−0.045 (2)
F6	0.133 (4)	0.1022 (16)	0.078 (2)	−0.008 (2)	0.057 (2)	0.0078 (15)
F3'	0.113 (4)	0.232 (15)	0.069 (3)	−0.042 (7)	0.016 (3)	−0.021 (5)
F4'	0.097 (5)	0.093 (6)	0.262 (19)	−0.011 (4)	0.059 (8)	−0.091 (9)
F2'	0.068 (5)	0.180 (13)	0.098 (9)	−0.020 (6)	−0.007 (5)	−0.075 (9)
F1'	0.204 (13)	0.046 (4)	0.164 (9)	−0.014 (6)	0.056 (9)	0.008 (5)
F5'	0.115 (6)	0.092 (3)	0.088 (5)	−0.015 (4)	0.061 (5)	−0.010 (4)
F6'	0.069 (3)	0.110 (5)	0.092 (5)	0.035 (3)	0.002 (3)	−0.022 (4)

C26—C27	1.387 (2)	C19—H19	0.9300
C26—C25	1.391 (2)	C10—H10	0.9300
C26—C29	1.474 (2)	C1—C2	1.373 (3)
C22—C21	1.188 (2)	C1—H1	0.9300
C22—C23	1.439 (2)	C16—C17	1.364 (3)
C23—C24	1.385 (2)	C16—H16	0.9300
C23—C28	1.393 (2)	C17—C18	1.364 (3)
C12—C11	1.387 (2)	C17—H17	0.9300
C12—C13	1.394 (2)	C4—C3	1.364 (4)
C12—C30	1.474 (2)	C4—C5	1.385 (3)
C7—C8	1.192 (2)	C4—H4	0.9300
C7—C6	1.430 (2)	C18—H18	0.9300
C20—C19	1.380 (2)	C2—C3	1.350 (4)
C20—C15	1.388 (2)	C2—H2	0.9300
C20—C21	1.432 (2)	C5—H5	0.9300
C11—C10	1.370 (2)	C3—H3	0.9300
C11—H11	0.9300	C29—C30	1.347 (2)
C9—C14	1.380 (2)	C29—C33	1.490 (2)
C9—C10	1.390 (2)	C30—C31	1.498 (2)
C9—C8	1.435 (2)	C31—F2'	1.266 (17)
C27—C28	1.372 (2)	C31—F1'	1.350 (15)
C27—H27	0.9300	C31—F2	1.351 (7)
C28—H28	0.9300	C31—F1	1.380 (8)
C24—C25	1.376 (2)	C31—C32	1.522 (3)
C24—H24	0.9300	C33—F5'	1.251 (6)
C25—H25	0.9300	C33—F5	1.273 (4)
C6—C1	1.370 (3)	C33—F6	1.435 (5)
C6—C5	1.374 (3)	C33—C32	1.503 (3)
C14—C13	1.377 (2)	C33—F6'	1.546 (8)
C14—H14	0.9300	C32—F4'	1.151 (7)
C13—H13	0.9300	C32—F4	1.297 (4)
C15—C16	1.371 (3)	C32—F3	1.421 (4)
C15—H15	0.9300	C32—F3'	1.563 (11)
C19—C18	1.381 (3)
C27—C26—C25	118.64 (15)	C3—C4—C5	120.3 (3)
C27—C26—C29	118.91 (14)	C3—C4—H4	119.9
C25—C26—C29	122.44 (15)	C5—C4—H4	119.9
C21—C22—C23	179.6 (2)	C17—C18—C19	120.2 (2)
C24—C23—C28	118.35 (16)	C17—C18—H18	119.9
C24—C23—C22	121.37 (15)	C19—C18—H18	119.9
C28—C23—C22	120.28 (16)	C3—C2—C1	120.4 (3)
C11—C12—C13	117.76 (15)	C3—C2—H2	119.8
C11—C12—C30	120.50 (14)	C1—C2—H2	119.8
C13—C12—C30	121.67 (14)	C6—C5—C4	119.8 (2)
C8—C7—C6	179.4 (2)	C6—C5—H5	120.1
C19—C20—C15	118.71 (17)	C4—C5—H5	120.1
C19—C20—C21	121.46 (16)	C2—C3—C4	119.9 (2)
C15—C20—C21	119.82 (16)	C2—C3—H3	120.0
C10—C11—C12	121.15 (15)	C4—C3—H3	120.0
C10—C11—H11	119.4	C30—C29—C26	128.39 (14)
C12—C11—H11	119.4	C30—C29—C33	111.11 (15)
C14—C9—C10	118.09 (16)	C26—C29—C33	120.24 (14)
C14—C9—C8	122.16 (16)	C29—C30—C12	128.56 (15)
C10—C9—C8	119.71 (16)	C29—C30—C31	110.29 (14)
C22—C21—C20	177.5 (2)	C12—C30—C31	121.10 (14)
C28—C27—C26	121.08 (15)	F2'—C31—F1'	109.8 (12)
C28—C27—H27	119.5	F2'—C31—F2	93.8 (10)
C26—C27—H27	119.5	F1'—C31—F1	119.5 (9)
C27—C28—C23	120.46 (16)	F2—C31—F1	103.8 (5)
C27—C28—H28	119.8	F2'—C31—C30	112.8 (9)
C23—C28—H28	119.8	F1'—C31—C30	108.2 (7)
C7—C8—C9	176.0 (2)	F2—C31—C30	115.1 (3)
C25—C24—C23	121.32 (15)	F1—C31—C30	112.2 (4)
C25—C24—H24	119.3	F2'—C31—C32	116.8 (10)
C23—C24—H24	119.3	F1'—C31—C32	103.1 (7)
C24—C25—C26	120.14 (16)	F2—C31—C32	113.1 (3)
C24—C25—H25	119.9	F1—C31—C32	107.1 (4)
C26—C25—H25	119.9	C30—C31—C32	105.42 (14)
C1—C6—C5	118.96 (19)	F5'—C33—F5	68.6 (5)
C1—C6—C7	120.71 (18)	F5—C33—F6	105.1 (2)
C5—C6—C7	120.3 (2)	F5'—C33—C29	117.4 (3)
C13—C14—C9	121.02 (16)	F5—C33—C29	118.5 (3)
C13—C14—H14	119.5	F6—C33—C29	108.1 (2)
C9—C14—H14	119.5	F5'—C33—C32	127.6 (5)
C14—C13—C12	120.90 (16)	F5—C33—C32	114.8 (3)
C14—C13—H13	119.5	F6—C33—C32	103.1 (3)
C12—C13—H13	119.5	C29—C33—C32	106.09 (15)
C16—C15—C20	120.58 (19)	F5'—C33—F6'	98.8 (4)
C16—C15—H15	119.7	F6—C33—F6'	135.2 (4)
C20—C15—H15	119.7	C29—C33—F6'	102.4 (4)
C20—C19—C18	120.1 (2)	C32—C33—F6'	98.9 (4)
C20—C19—H19	120.0	F4'—C32—F4	60.9 (10)
C18—C19—H19	120.0	F4—C32—F3	104.6 (3)
C11—C10—C9	121.03 (16)	F4'—C32—C33	122.9 (4)
C11—C10—H10	119.5	F4—C32—C33	119.7 (3)
C9—C10—H10	119.5	F3—C32—C33	105.1 (3)
C6—C1—C2	120.6 (2)	F4'—C32—C31	126.0 (6)
C6—C1—H1	119.7	F4—C32—C31	115.8 (2)
C2—C1—H1	119.7	F3—C32—C31	104.8 (2)
C17—C16—C15	120.0 (2)	C33—C32—C31	105.32 (16)
C17—C16—H16	120.0	F4'—C32—F3'	101.8 (7)
C15—C16—H16	120.0	F3—C32—F3'	145.5 (6)
C16—C17—C18	120.3 (2)	C33—C32—F3'	91.0 (6)
C16—C17—H17	119.8	C31—C32—F3'	99.8 (5)
C18—C17—H17	119.8
C13—C12—C11—C10	−0.4 (3)	C26—C29—C33—F5'	30.1 (8)
C30—C12—C11—C10	176.79 (17)	C30—C29—C33—F5	136.2 (4)
C25—C26—C27—C28	−0.4 (2)	C26—C29—C33—F5	−49.2 (4)
C29—C26—C27—C28	178.34 (15)	C30—C29—C33—F6	−104.6 (3)
C26—C27—C28—C23	0.8 (3)	C26—C29—C33—F6	70.0 (3)
C24—C23—C28—C27	−0.4 (3)	C30—C29—C33—C32	5.4 (2)
C22—C23—C28—C27	−179.93 (16)	C26—C29—C33—C32	−179.99 (16)
C28—C23—C24—C25	−0.6 (3)	C30—C29—C33—F6'	108.6 (5)
C22—C23—C24—C25	179.00 (16)	C26—C29—C33—F6'	−76.8 (5)
C23—C24—C25—C26	1.0 (3)	F5'—C33—C32—F4'	−71 (2)
C27—C26—C25—C24	−0.5 (2)	F5—C33—C32—F4'	10.4 (18)
C29—C26—C25—C24	−179.20 (15)	F6—C33—C32—F4'	−103.3 (17)
C10—C9—C14—C13	−1.8 (3)	C29—C33—C32—F4'	143.2 (15)
C8—C9—C14—C13	176.01 (19)	F6'—C33—C32—F4'	37.4 (19)
C9—C14—C13—C12	−0.1 (3)	F5'—C33—C32—F4	1.7 (11)
C11—C12—C13—C14	1.2 (3)	F5—C33—C32—F4	83.1 (6)
C30—C12—C13—C14	−176.01 (17)	F6—C33—C32—F4	−30.6 (5)
C19—C20—C15—C16	−0.8 (3)	C29—C33—C32—F4	−144.1 (3)
C21—C20—C15—C16	177.85 (18)	F6'—C33—C32—F4	110.1 (7)
C15—C20—C19—C18	1.4 (3)	F5'—C33—C32—F3	−115.4 (10)
C21—C20—C19—C18	−177.18 (19)	F5—C33—C32—F3	−34.0 (5)
C12—C11—C10—C9	−1.5 (3)	F6—C33—C32—F3	−147.7 (4)
C14—C9—C10—C11	2.5 (3)	C29—C33—C32—F3	98.8 (3)
C8—C9—C10—C11	−175.31 (19)	F6'—C33—C32—F3	−6.9 (6)
C5—C6—C1—C2	0.7 (3)	F5'—C33—C32—C31	134.3 (8)
C7—C6—C1—C2	−179.4 (2)	F5—C33—C32—C31	−144.4 (4)
C20—C15—C16—C17	−0.5 (3)	F6—C33—C32—C31	102.0 (3)
C15—C16—C17—C18	1.1 (4)	C29—C33—C32—C31	−11.5 (2)
C16—C17—C18—C19	−0.5 (4)	F6'—C33—C32—C31	−117.3 (5)
C20—C19—C18—C17	−0.8 (3)	F5'—C33—C32—F3'	33.8 (13)
C6—C1—C2—C3	0.6 (4)	F5—C33—C32—F3'	115.2 (9)
C1—C6—C5—C4	−1.2 (4)	F6—C33—C32—F3'	1.5 (8)
C7—C6—C5—C4	178.9 (2)	C29—C33—C32—F3'	−112.0 (6)
C3—C4—C5—C6	0.4 (5)	F6'—C33—C32—F3'	142.3 (10)
C1—C2—C3—C4	−1.3 (4)	F2'—C31—C32—F4'	93.4 (19)
C5—C4—C3—C2	0.8 (5)	F1'—C31—C32—F4'	−27 (2)
C27—C26—C29—C30	52.6 (2)	F2—C31—C32—F4'	−13.8 (15)
C25—C26—C29—C30	−128.69 (18)	F1—C31—C32—F4'	99.9 (15)
C27—C26—C29—C33	−120.95 (18)	C30—C31—C32—F4'	−140.4 (15)
C25—C26—C29—C33	57.7 (2)	F2'—C31—C32—F4	21.9 (11)
C26—C29—C30—C12	11.8 (3)	F1'—C31—C32—F4	−98.6 (10)
C33—C29—C30—C12	−174.18 (16)	F2—C31—C32—F4	−85.4 (5)
C26—C29—C30—C31	−170.71 (15)	F1—C31—C32—F4	28.3 (6)
C33—C29—C30—C31	3.3 (2)	C30—C31—C32—F4	148.0 (4)
C11—C12—C30—C29	28.9 (3)	F2'—C31—C32—F3	136.5 (11)
C13—C12—C30—C29	−153.99 (18)	F1'—C31—C32—F3	16.0 (10)
C11—C12—C30—C31	−148.36 (17)	F2—C31—C32—F3	29.3 (4)
C13—C12—C30—C31	28.7 (2)	F1—C31—C32—F3	143.0 (5)
C29—C30—C31—F2'	118.0 (11)	C30—C31—C32—F3	−97.3 (3)
C12—C30—C31—F2'	−64.3 (11)	F2'—C31—C32—C33	−112.9 (10)
C29—C30—C31—F1'	−120.4 (8)	F1'—C31—C32—C33	126.7 (8)
C12—C30—C31—F1'	57.4 (8)	F2—C31—C32—C33	139.9 (3)
C29—C30—C31—F2	−136.0 (3)	F1—C31—C32—C33	−106.4 (4)
C12—C30—C31—F2	41.8 (3)	C30—C31—C32—C33	13.3 (2)
C29—C30—C31—F1	105.7 (5)	F2'—C31—C32—F3'	−19.1 (13)
C12—C30—C31—F1	−76.6 (5)	F1'—C31—C32—F3'	−139.6 (13)
C29—C30—C31—C32	−10.6 (2)	F2—C31—C32—F3'	−126.4 (8)
C12—C30—C31—C32	167.15 (16)	F1—C31—C32—F3'	−12.7 (8)
C30—C29—C33—F5'	−144.5 (8)	C30—C31—C32—F3'	107.0 (7)