3,3,4,4,5,5-Hexa­fluoro-1,2-bis[4-(phenyl­ethyn­yl)phen­yl]­cyclo­pentene

Liu, S.; Chen, B.

doi:10.1107/S1600536809052040

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o129

doi:10.1107/S1600536809052040

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3,3,4,4,5,5-Hexafluoro-1,2-bis[4-(phenylethynyl)phenyl]cyclopentene

Shaoqian Liu ^a and Bing Chen ^a ^*

^aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: wjcblc@sina.com

(Received 30 October 2009; accepted 3 December 2009; online 12 December 2009)

The title compound, C₃₃H₁₈F₆, has a V-shaped conjugated subunit. The dihedral angles between the central cyclopentene 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_r = 528.47
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.109
S = 1.01
6087 reflections
407 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

Left-handed material is a kind of material that exhibits a negative refraction index. It has been explored theoretically by Veselago (1968). In 2000, a two-dimensional isotropic left-handed material was verified showing a negative refraction index (Shelby et al., 2000). From then on, the study of left-handed materials has gained increasing interest in physics-related fields. So far, most of the left-handed materials were realised via micro-processing technologies to integrate a metal into a S-shape (Chen et al., 2004) or H-shape (Zhou et al., 2006) micro-structural unit, therefore achieving a periodic arrangement. However, due to the technology limitations of nano-scale processing technology, most of the successful experimental verification are carried out in the microwave band (Zhang et al., 2005; Liu et al., 2007). Only if the left-handed material structural unit achieves a smaller size, a negative refraction index might be realised in the visible range. Using concepts of chemical synthesis technology to create structural features of left-handed materials at the molecular level might show potential to realise negative refraction in the visible range. The molecular model should exhibit an extended conjugated system providing electrons that are easily excited.

In this article, we tried to simulate structural features of left-handed material and designed a V-shaped conjugated organic molecular structure (Fig. 1). The title compound turns out to be a single-crystal, but whether it is really close to the structural features of left-handed materials or not and how to modify it to exhibit negative refraction, is still under investigation. The dihedral angle between the benzene ring C9—C14 and the adjacent benzene ring C1—C6 is 31.4 (1) °, the dihedral angle between the benzene ring C23—C28 and the adjacent benzene ring C15—C20 is 50.7 (2) °. C7—C8 (1.192 (2) Å) and C21—C22 (1.188 (2) Å) are acetylenic bonds and are therefore significantly shorter than the other carbon carbon bonds. The fluoro substituents at the cyclopentene ring are disordered with occupancies refined to a 0.675 (2):0.325 (2) ratio.

Related literature top

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 top

Synthesis of the title compound was carried out in two steps:(1) 4-bromo-1-phenylethynylbenzene,was obtained in 72.6% yield by the reaction of phenylacetylene (12 g, 0.1 mol) and 1-Bromo-4-iodobenzene (28.29, 0.1 mol) in N(C₂H₅)₃ (150 ml) solution catalyzed by CuI (0.3 g, 1.55 mmol), PPh₃ (0.6 g, 2.45 mmol) and Pd(PPh₃)Cl₂(0.3 g, 0.42 mmol) at 336 K; (2) 1.6 ml of n-BuLi/hexane solution (2.5 mol/L, 4.0 mmol) was added slowly at 195 K under a nitrogen atmosphere to a stirred THF solution (40 ml) containing 4-bromo-1-phenylethynylbenzene (1.03 g, 4 mmol). After 30 min perfluorocyclopentene (0.27 ml, 2 mmol) was added and the mixture was stirred for 1 h at this temperature. The reaction mixture was extracted with CHCl₃, evaporated in vacuo and purifed by column chromatography (hexane) to give the title compound. After recrystallization from CH₂Cl₂ light yellow-green crystals of the title compound were obtained in 23.4% yield. ¹HNMR (400 MHz, CDCl₃): δ 7.35(m, 10H), 7.51 (m, 8H)

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure showing the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

3,3,4,4,5,5-Hexafluoro-1,2-bis[4-(phenylethynyl)phenyl]cyclopentene top

Crystal data top

C₃₃H₁₈F₆	F(000) = 1080
M_r = 528.47	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0298P)² + 0.8178P] where P = (F_o² + 2F_c²)/3
6087 reflections	(Δ/σ)_max = 0.002
407 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₃₃H₁₈F₆	V = 2653.6 (4) Å³
M_r = 528.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.350 (1) Å	µ = 0.11 mm⁻¹
b = 9.2893 (7) Å	T = 296 K
c = 17.980 (1) Å	0.45 × 0.41 × 0.38 mm
β = 103.654 (1)°

Data collection top

Bruker APEXII CCD diffractometer	6087 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3767 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.961	R_int = 0.026
22979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.01	Δρ_max = 0.14 e Å⁻³
6087 reflections	Δρ_min = −0.19 e Å⁻³
407 parameters

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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₃₃H₁₈F₆
M_r	528.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.350 (1), 9.2893 (7), 17.980 (1)
β (°)	103.654 (1)
V (Å³)	2653.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.45 × 0.41 × 0.38

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.954, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	22979, 6087, 3767
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.109, 1.01
No. of reflections	6087
No. of parameters	407
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, H. S., Ran, L. X., Huangfu, J. T., Zhang, X. M., Chen, K. S., Grzegorczyk, T. M. & Kong, J. A. (2004). Phys. Rev. E70, 057605. Google Scholar
Liu, R. P., Degiron, A., Mock, J. J. & Smith, D. R. (2007). Appl. Phys. Lett. 90, 263504. Web of Science CrossRef Google Scholar
Shelby, R. A., Smith, D. R., Nemat-Nasser, S. C. & Schultz, S. (2000). Appl. Phys. Lett. 78, 489–491. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Veselago, V. G. (1968). Sov. Phys. Usp. 10, 509–514. CrossRef Web of Science Google Scholar
Zhang, S., Fan, W. J., Panoiu, N. C., Malloy, K. J., Osgood, R. M. & Brueck, S. R. J. (2005). Phys. Rev. Lett. 95, 137404. Web of Science CrossRef PubMed Google Scholar
Zhou, J. F., Koschny, T., Zhang, L., Tuttle, G. & Soukoulis, C. M. (2006). Appl. Phys. Lett. 88, 221103. Web of Science CrossRef Google Scholar