2,2,2-Trifluoro-1-[3-(2,2,2-trifluoro­acet­yl)azulen-1-yl]ethanone

Förster, S.; Eissmann, F.; Seichter, W.; Weber, E.

doi:10.1107/S1600536811017569

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1419

doi:10.1107/S1600536811017569

Open

access

2,2,2-Trifluoro-1-[3-(2,2,2-trifluoroacetyl)azulen-1-yl]ethanone

Sebastian Förster,^a Frank Eissmann,^a Wilhelm Seichter ^a and Edwin Weber ^a ^*

^aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
^*Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

(Received 18 April 2011; accepted 10 May 2011; online 14 May 2011)

There are two molecules in the asymmetric unit of the title compound, C₁₄H₆F₆O₂, in which the azulene systems possess an almost planar geometry with maximum deviations of 0.0438 (15) and 0.0396 (14) Å. Besides intra- and intermolecular C—H⋯O and C—H⋯F interactions, the structure displays three F⋯F contacts [2.793 (2), 2.8820 (17) and 2.9181 (16) Å]. Furthermore, a characteristic azulene π-stacking is observed with an alternating sequence of electron-rich five-membered rings and electron-deficient seven-membered rings [centroid–centroid distances = 3.5413 (12), 3.6847 (12), 3.5790 (12) and 3.7718 (12) Å].

Related literature

For the synthesis, see: Mathias & Overberger (1980 ); Zielinski et al. (2008 ). For the crystal structure of the parent azulene, see: Robertson et al. (1962 ). For halogen interactions in molecular crystal structures, see: Brammer et al. (2001 ); Metrangolo et al. (2008 ).

Experimental

Crystal data

C₁₄H₆F₆O₂
M_r = 320.19
Triclinic, $[P \overline 1]$
a = 7.1634 (2) Å
b = 10.8681 (4) Å
c = 16.3286 (5) Å
α = 81.544 (2)°
β = 83.310 (2)°
γ = 80.009 (2)°
V = 1232.92 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.40 × 0.14 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.933, T_max = 0.988
20089 measured reflections
5321 independent reflections
3680 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 1.02
5321 reflections
397 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯F3	0.95	2.40	2.916 (2)	114
C2A—H2A⋯F3A	0.95	2.45	2.972 (2)	115
C2A—H2A⋯F5A	0.95	2.50	2.968 (2)	111
C5—H5⋯O2	0.95	2.31	2.988 (2)	127
C5A—H5A⋯O2A	0.95	2.33	3.001 (2)	127
C6—H6⋯O2Aⁱ	0.95	2.52	3.236 (2)	133
C6A—H6A⋯O2ⁱ	0.95	2.47	3.160 (2)	130
C8—H8⋯F2Aⁱⁱ	0.95	2.45	3.358 (2)	160
C9—H9⋯O1	0.95	2.31	2.983 (2)	127
C9—H9⋯O1Aⁱⁱ	0.95	2.58	3.454 (2)	153
C9A—H9A⋯O1ⁱⁱ	0.95	2.50	3.352 (2)	149
C9A—H9A⋯O1A	0.95	2.31	2.993 (2)	128
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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 and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017569/im2284sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017569/im2284Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017569/im2284Isup3.mol

Supporting information file. DOI: 10.1107/S1600536811017569/im2284Isup4.cml

checkCIF report

Comment top

The asymmetric unit of the crystal structure contains two molecules featuring planar azulene ring systems (Fig 1). In the crystallographic b and c directions the structure is stabilized by hydrogen bonding both between the carbonyl oxygen or fluorine atoms and hydrogen atoms of the electronic deficient seven-membered ring (Fig 2). The crystal structure is characterized by formation of molecular stacks along the crystallographic a-axis (Fig 3). Due to the inherent dipole character of the azulene ring system, the molecules are arranged in a head-to-tail fashion within the stacks. Each molecule in the asymmetric unit shows two different interactions to its stack neighbors, which leads to four different distances between the centroids Cg1···Cg2ⁱ, d = 3.5413 (12), Cg1···Cg2ⁱⁱ, d = 3.6847 (12), Cg1A···Cg2Aⁱⁱⁱ, d = 3.5790 (12), Cg1A···Cg2A^iv, d = 3.7718 (12). Furthermore, three halogen···halogen contacts were observed: F5···F5 [d = 2.7931 (23) Å, θ₁ = θ₂ = 145.79 (14)°], F3···F6A [d = 2.8820 (17), θ₁ = 124.02 (11), θ₂ = 113.52 (12)] and F6A···F6 [d = 2.9181 (16), θ₁ = 161.89 (11), θ₂ = 156.90 (12)]. Symmetry codes: (i) = -x, 2 - y, -z; (ii) = 1 - x, 2 - y, -z; (iii) 1 - x, 2 - y, 1 - z; (iv) 2 - x, 2 - y, 1 - z.

Related literature top

For the synthesis, see: Mathias & Overberger (1980); Zielinski et al. (2008). For the crystal structure of the parent azulene, see: Robertson et al. (1962). For halogen interactions in molecular crystal structures, see: Brammer et al. (2001); Metrangolo et al. (2008).

Experimental top

The title compound was prepared according to the literature procedure of Mathias et al. (1980). Crystallization by slow evaporation from acetone yielded suitable crystals after 3 days.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Asymmetric unit of the title compound, showing the atom numbering schemes. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular sheets within the packing of the title compound. Intermolecular interactions are represented as dashed lines.
	Fig. 3. Packing diagram viewed down the a axis, showing the stacking interactions of the azulene systems.

2,2,2-Trifluoro-1-[3-(2,2,2-trifluoroacetyl)azulen-1-yl]ethanone top

Crystal data top

C₁₄H₆F₆O₂	Z = 4
M_r = 320.19	F(000) = 640
Triclinic, P1	D_x = 1.725 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1634 (2) Å	Cell parameters from 6112 reflections
b = 10.8681 (4) Å	θ = 2.9–28.9°
c = 16.3286 (5) Å	µ = 0.18 mm⁻¹
α = 81.544 (2)°	T = 100 K
β = 83.310 (2)°	Rod, red
γ = 80.009 (2)°	0.40 × 0.14 × 0.07 mm
V = 1232.92 (7) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	5321 independent reflections
Radiation source: fine-focus sealed tube	3680 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 27.1°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
T_min = 0.933, T_max = 0.988	k = −13→13
20089 measured reflections	l = −20→20

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0465P)² + 0.5715P] where P = (F_o² + 2F_c²)/3
5321 reflections	(Δ/σ)_max < 0.001
397 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₄H₆F₆O₂	γ = 80.009 (2)°
M_r = 320.19	V = 1232.92 (7) Å³
Triclinic, P1	Z = 4
a = 7.1634 (2) Å	Mo Kα radiation
b = 10.8681 (4) Å	µ = 0.18 mm⁻¹
c = 16.3286 (5) Å	T = 100 K
α = 81.544 (2)°	0.40 × 0.14 × 0.07 mm
β = 83.310 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5321 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3680 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.988	R_int = 0.031
20089 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.02	Δρ_max = 0.25 e Å⁻³
5321 reflections	Δρ_min = −0.31 e Å⁻³
397 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
F1	0.39463 (18)	0.60356 (13)	0.19502 (8)	0.0398 (3)
F2	0.2168 (2)	0.64770 (12)	0.30613 (7)	0.0412 (3)
F3	0.09017 (18)	0.61716 (11)	0.19949 (7)	0.0321 (3)
F4	0.36566 (18)	0.57475 (11)	−0.07337 (8)	0.0346 (3)
F5	0.05955 (18)	0.59590 (11)	−0.05863 (7)	0.0344 (3)
F6	0.2086 (2)	0.60122 (12)	−0.18071 (7)	0.0370 (3)
O1	0.2103 (2)	0.88041 (15)	0.24264 (9)	0.0379 (4)
O2	0.1713 (2)	0.84185 (14)	−0.17976 (8)	0.0319 (4)
C1	0.2215 (3)	0.84447 (19)	0.10164 (11)	0.0204 (4)
C2	0.2071 (3)	0.76448 (18)	0.04375 (11)	0.0195 (4)
H2	0.1961	0.6778	0.0568	0.023*
C3	0.2114 (3)	0.83168 (18)	−0.03648 (11)	0.0192 (4)
C4	0.2344 (2)	0.95792 (18)	−0.03047 (11)	0.0188 (4)
C5	0.2515 (3)	1.05229 (18)	−0.09710 (12)	0.0213 (4)
H5	0.2413	1.0298	−0.1503	0.026*
C6	0.2813 (3)	1.17487 (19)	−0.09636 (12)	0.0237 (4)
H6	0.2861	1.2254	−0.1490	0.028*
C7	0.3050 (3)	1.23385 (19)	−0.02918 (13)	0.0246 (4)
H7	0.3251	1.3189	−0.0424	0.030*
C8	0.3033 (3)	1.18607 (19)	0.05439 (13)	0.0240 (4)
H8	0.3249	1.2427	0.0901	0.029*
C9	0.2749 (3)	1.06782 (19)	0.09354 (12)	0.0223 (4)
H9	0.2777	1.0549	0.1522	0.027*
C10	0.2428 (3)	0.96584 (18)	0.05790 (11)	0.0194 (4)
C11	0.2178 (3)	0.8089 (2)	0.19135 (12)	0.0243 (4)
C12	0.2291 (3)	0.6679 (2)	0.22329 (12)	0.0280 (5)
C13	0.1949 (3)	0.78107 (19)	−0.11202 (12)	0.0223 (4)
C14	0.2074 (3)	0.6369 (2)	−0.10652 (12)	0.0257 (5)
F1A	0.82283 (17)	0.62221 (12)	0.68301 (8)	0.0367 (3)
F2A	0.6196 (2)	0.67680 (12)	0.78398 (7)	0.0382 (3)
F3A	0.52235 (17)	0.63290 (11)	0.67388 (7)	0.0307 (3)
F4A	0.86640 (18)	0.55033 (11)	0.42077 (8)	0.0373 (3)
F5A	0.56351 (17)	0.59936 (12)	0.41519 (8)	0.0346 (3)
F6A	0.7480 (2)	0.57401 (12)	0.30349 (8)	0.0413 (3)
O1A	0.6058 (2)	0.90591 (14)	0.71153 (8)	0.0314 (4)
O2A	0.7788 (2)	0.80970 (14)	0.29118 (8)	0.0320 (4)
C1A	0.6844 (3)	0.85148 (18)	0.57393 (11)	0.0185 (4)
C2A	0.6948 (3)	0.76475 (18)	0.51849 (11)	0.0193 (4)
H2A	0.6756	0.6797	0.5335	0.023*
C3A	0.7379 (3)	0.82104 (18)	0.43672 (11)	0.0187 (4)
C4A	0.7618 (2)	0.94807 (18)	0.44046 (11)	0.0175 (4)
C5A	0.8140 (3)	1.03354 (18)	0.37289 (12)	0.0203 (4)
H5A	0.8301	1.0040	0.3202	0.024*
C6A	0.8452 (3)	1.15565 (18)	0.37253 (12)	0.0217 (4)
H6A	0.8807	1.1984	0.3194	0.026*
C7A	0.8324 (3)	1.22506 (18)	0.43871 (12)	0.0218 (4)
H7A	0.8577	1.3089	0.4243	0.026*
C8A	0.7876 (3)	1.18895 (18)	0.52299 (12)	0.0212 (4)
H8A	0.7898	1.2507	0.5583	0.025*
C9A	0.7401 (3)	1.07489 (18)	0.56275 (12)	0.0203 (4)
H9A	0.7133	1.0694	0.6214	0.024*
C10A	0.7267 (2)	0.96792 (17)	0.52800 (11)	0.0174 (4)
C11A	0.6426 (3)	0.82740 (19)	0.66380 (12)	0.0220 (4)
C12A	0.6515 (3)	0.6882 (2)	0.70151 (12)	0.0254 (4)
C13A	0.7520 (3)	0.76079 (19)	0.36250 (12)	0.0223 (4)
C14A	0.7319 (3)	0.6197 (2)	0.37514 (13)	0.0271 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0358 (7)	0.0393 (8)	0.0377 (7)	0.0061 (6)	−0.0025 (6)	0.0019 (6)
F2	0.0649 (9)	0.0404 (8)	0.0172 (6)	−0.0087 (7)	−0.0069 (6)	0.0030 (5)
F3	0.0401 (7)	0.0298 (7)	0.0280 (7)	−0.0146 (6)	−0.0019 (5)	0.0006 (5)
F4	0.0390 (7)	0.0265 (7)	0.0354 (7)	0.0019 (6)	−0.0017 (6)	−0.0048 (5)
F5	0.0405 (8)	0.0299 (7)	0.0340 (7)	−0.0169 (6)	0.0104 (6)	−0.0059 (5)
F6	0.0578 (9)	0.0325 (7)	0.0242 (7)	−0.0138 (6)	0.0020 (6)	−0.0121 (5)
O1	0.0591 (11)	0.0384 (9)	0.0216 (8)	−0.0204 (8)	−0.0042 (7)	−0.0064 (7)
O2	0.0502 (10)	0.0284 (8)	0.0186 (8)	−0.0108 (7)	−0.0062 (7)	−0.0003 (6)
C1	0.0179 (9)	0.0263 (11)	0.0178 (10)	−0.0050 (8)	−0.0018 (7)	−0.0034 (8)
C2	0.0168 (9)	0.0215 (10)	0.0199 (10)	−0.0039 (8)	−0.0011 (7)	−0.0015 (8)
C3	0.0172 (9)	0.0225 (10)	0.0182 (9)	−0.0039 (8)	−0.0009 (7)	−0.0033 (7)
C4	0.0131 (9)	0.0228 (10)	0.0205 (10)	−0.0030 (7)	−0.0013 (7)	−0.0031 (8)
C5	0.0174 (10)	0.0264 (11)	0.0206 (10)	−0.0036 (8)	−0.0029 (7)	−0.0044 (8)
C6	0.0213 (10)	0.0245 (11)	0.0248 (11)	−0.0054 (8)	−0.0031 (8)	0.0011 (8)
C7	0.0198 (10)	0.0203 (11)	0.0342 (12)	−0.0040 (8)	−0.0026 (8)	−0.0038 (8)
C8	0.0199 (10)	0.0235 (11)	0.0310 (11)	−0.0040 (8)	−0.0048 (8)	−0.0086 (8)
C9	0.0168 (9)	0.0285 (11)	0.0228 (10)	−0.0029 (8)	−0.0052 (8)	−0.0055 (8)
C10	0.0130 (9)	0.0250 (11)	0.0206 (10)	−0.0035 (8)	−0.0015 (7)	−0.0032 (8)
C11	0.0239 (10)	0.0310 (12)	0.0196 (10)	−0.0082 (9)	−0.0030 (8)	−0.0033 (8)
C12	0.0336 (12)	0.0314 (12)	0.0179 (10)	−0.0046 (9)	−0.0029 (8)	0.0000 (8)
C13	0.0216 (10)	0.0261 (11)	0.0195 (10)	−0.0061 (8)	0.0017 (8)	−0.0044 (8)
C14	0.0318 (11)	0.0277 (11)	0.0182 (10)	−0.0078 (9)	0.0034 (8)	−0.0055 (8)
F1A	0.0294 (7)	0.0335 (7)	0.0415 (8)	−0.0003 (6)	−0.0045 (6)	0.0092 (6)
F2A	0.0566 (9)	0.0413 (8)	0.0189 (6)	−0.0200 (7)	−0.0048 (6)	0.0043 (5)
F3A	0.0363 (7)	0.0295 (7)	0.0293 (7)	−0.0159 (5)	−0.0057 (5)	0.0010 (5)
F4A	0.0389 (7)	0.0231 (7)	0.0484 (8)	−0.0008 (6)	−0.0043 (6)	−0.0048 (6)
F5A	0.0330 (7)	0.0371 (8)	0.0383 (7)	−0.0175 (6)	0.0070 (5)	−0.0142 (6)
F6A	0.0581 (9)	0.0388 (8)	0.0341 (7)	−0.0221 (7)	0.0097 (6)	−0.0217 (6)
O1A	0.0429 (9)	0.0332 (9)	0.0212 (7)	−0.0150 (7)	0.0010 (6)	−0.0065 (6)
O2A	0.0481 (10)	0.0293 (8)	0.0194 (8)	−0.0081 (7)	−0.0021 (7)	−0.0043 (6)
C1A	0.0158 (9)	0.0224 (10)	0.0180 (9)	−0.0038 (8)	−0.0034 (7)	−0.0027 (7)
C2A	0.0156 (9)	0.0191 (10)	0.0229 (10)	−0.0030 (7)	−0.0038 (7)	−0.0001 (8)
C3A	0.0167 (9)	0.0219 (10)	0.0184 (9)	−0.0039 (8)	−0.0022 (7)	−0.0043 (8)
C4A	0.0130 (9)	0.0209 (10)	0.0181 (9)	−0.0014 (7)	−0.0034 (7)	−0.0011 (7)
C5A	0.0177 (9)	0.0245 (11)	0.0185 (9)	−0.0017 (8)	−0.0023 (7)	−0.0042 (8)
C6A	0.0190 (10)	0.0247 (11)	0.0204 (10)	−0.0042 (8)	−0.0016 (8)	0.0012 (8)
C7A	0.0176 (10)	0.0207 (10)	0.0270 (11)	−0.0034 (8)	−0.0047 (8)	−0.0009 (8)
C8A	0.0179 (10)	0.0201 (10)	0.0267 (11)	−0.0024 (8)	−0.0043 (8)	−0.0060 (8)
C9A	0.0150 (9)	0.0266 (11)	0.0195 (10)	−0.0018 (8)	−0.0036 (7)	−0.0043 (8)
C10A	0.0118 (9)	0.0220 (10)	0.0186 (9)	−0.0025 (7)	−0.0021 (7)	−0.0026 (7)
C11A	0.0186 (10)	0.0297 (11)	0.0193 (10)	−0.0082 (8)	−0.0026 (7)	−0.0024 (8)
C12A	0.0286 (11)	0.0308 (12)	0.0179 (10)	−0.0098 (9)	−0.0031 (8)	0.0004 (8)
C13A	0.0203 (10)	0.0262 (11)	0.0217 (10)	−0.0051 (8)	−0.0022 (8)	−0.0054 (8)
C14A	0.0298 (11)	0.0284 (12)	0.0256 (11)	−0.0079 (9)	0.0021 (9)	−0.0119 (9)

Geometric parameters (Å, º) top

F1—C12	1.337 (2)	F1A—C12A	1.336 (2)
F2—C12	1.333 (2)	F2A—C12A	1.330 (2)
F3—C12	1.337 (2)	F3A—C12A	1.338 (2)
F4—C14	1.343 (2)	F4A—C14A	1.342 (3)
F5—C14	1.341 (2)	F5A—C14A	1.341 (2)
F6—C14	1.324 (2)	F6A—C14A	1.322 (2)
O1—C11	1.214 (2)	O1A—C11A	1.214 (2)
O2—C13	1.216 (2)	O2A—C13A	1.215 (2)
C1—C2	1.398 (3)	C1A—C2A	1.387 (3)
C1—C10	1.428 (3)	C1A—C10A	1.434 (3)
C1—C11	1.457 (3)	C1A—C11A	1.457 (3)
C2—C3	1.403 (3)	C2A—C3A	1.408 (3)
C2—H2	0.9500	C2A—H2A	0.9500
C3—C4	1.429 (3)	C3A—C4A	1.431 (3)
C3—C13	1.447 (3)	C3A—C13A	1.446 (3)
C4—C5	1.391 (3)	C4A—C5A	1.394 (3)
C4—C10	1.467 (3)	C4A—C10A	1.463 (2)
C5—C6	1.387 (3)	C5A—C6A	1.383 (3)
C5—H5	0.9500	C5A—H5A	0.9500
C6—C7	1.390 (3)	C6A—C7A	1.392 (3)
C6—H6	0.9500	C6A—H6A	0.9500
C7—C8	1.386 (3)	C7A—C8A	1.390 (3)
C7—H7	0.9500	C7A—H7A	0.9500
C8—C9	1.386 (3)	C8A—C9A	1.390 (3)
C8—H8	0.9500	C8A—H8A	0.9500
C9—C10	1.389 (3)	C9A—C10A	1.389 (3)
C9—H9	0.9500	C9A—H9A	0.9500
C11—C12	1.536 (3)	C11A—C12A	1.541 (3)
C13—C14	1.544 (3)	C13A—C14A	1.546 (3)

C2—C1—C10	108.52 (16)	C2A—C1A—C10A	108.39 (16)
C2—C1—C11	125.49 (18)	C2A—C1A—C11A	125.81 (17)
C10—C1—C11	125.99 (17)	C10A—C1A—C11A	125.78 (17)
C1—C2—C3	109.69 (17)	C1A—C2A—C3A	110.12 (17)
C1—C2—H2	125.2	C1A—C2A—H2A	124.9
C3—C2—H2	125.2	C3A—C2A—H2A	124.9
C2—C3—C4	108.25 (16)	C2A—C3A—C4A	107.87 (16)
C2—C3—C13	125.54 (18)	C2A—C3A—C13A	125.59 (18)
C4—C3—C13	126.20 (17)	C4A—C3A—C13A	126.53 (17)
C5—C4—C3	125.52 (17)	C5A—C4A—C3A	125.60 (17)
C5—C4—C10	127.61 (17)	C5A—C4A—C10A	127.54 (17)
C3—C4—C10	106.84 (16)	C3A—C4A—C10A	106.85 (15)
C6—C5—C4	128.73 (18)	C6A—C5A—C4A	128.50 (18)
C6—C5—H5	115.6	C6A—C5A—H5A	115.7
C4—C5—H5	115.6	C4A—C5A—H5A	115.7
C5—C6—C7	128.88 (19)	C5A—C6A—C7A	129.35 (18)
C5—C6—H6	115.6	C5A—C6A—H6A	115.3
C7—C6—H6	115.6	C7A—C6A—H6A	115.3
C8—C7—C6	129.13 (19)	C8A—C7A—C6A	129.10 (19)
C8—C7—H7	115.4	C8A—C7A—H7A	115.5
C6—C7—H7	115.4	C6A—C7A—H7A	115.5
C7—C8—C9	129.54 (19)	C7A—C8A—C9A	128.92 (18)
C7—C8—H8	115.2	C7A—C8A—H8A	115.5
C9—C8—H8	115.2	C9A—C8A—H8A	115.5
C10—C9—C8	128.27 (18)	C10A—C9A—C8A	128.53 (18)
C10—C9—H9	115.9	C10A—C9A—H9A	115.7
C8—C9—H9	115.9	C8A—C9A—H9A	115.7
C9—C10—C1	125.46 (17)	C9A—C10A—C1A	125.14 (17)
C9—C10—C4	127.81 (18)	C9A—C10A—C4A	128.04 (17)
C1—C10—C4	106.65 (16)	C1A—C10A—C4A	106.74 (15)
O1—C11—C1	125.8 (2)	O1A—C11A—C1A	126.36 (19)
O1—C11—C12	117.38 (18)	O1A—C11A—C12A	117.31 (17)
C1—C11—C12	116.78 (17)	C1A—C11A—C12A	116.31 (17)
F2—C12—F1	107.72 (17)	F2A—C12A—F1A	107.42 (16)
F2—C12—F3	107.00 (17)	F2A—C12A—F3A	107.06 (16)
F1—C12—F3	107.28 (17)	F1A—C12A—F3A	107.55 (16)
F2—C12—C11	111.20 (17)	F2A—C12A—C11A	111.26 (16)
F1—C12—C11	110.51 (17)	F1A—C12A—C11A	110.94 (16)
F3—C12—C11	112.90 (17)	F3A—C12A—C11A	112.37 (16)
O2—C13—C3	125.94 (19)	O2A—C13A—C3A	126.57 (19)
O2—C13—C14	116.69 (17)	O2A—C13A—C14A	116.71 (17)
C3—C13—C14	117.37 (17)	C3A—C13A—C14A	116.72 (17)
F6—C14—F5	107.30 (16)	F6A—C14A—F4A	107.38 (17)
F6—C14—F4	107.41 (16)	F6A—C14A—F5A	107.43 (16)
F5—C14—F4	106.68 (16)	F4A—C14A—F5A	106.64 (17)
F6—C14—C13	111.59 (16)	F6A—C14A—C13A	111.71 (17)
F5—C14—C13	111.68 (16)	F4A—C14A—C13A	111.30 (16)
F4—C14—C13	111.89 (16)	F5A—C14A—C13A	112.10 (16)

C10—C1—C2—C3	−2.2 (2)	C10A—C1A—C2A—C3A	−1.5 (2)
C11—C1—C2—C3	178.56 (18)	C11A—C1A—C2A—C3A	179.96 (17)
C1—C2—C3—C4	1.6 (2)	C1A—C2A—C3A—C4A	1.8 (2)
C1—C2—C3—C13	−178.33 (18)	C1A—C2A—C3A—C13A	−177.22 (17)
C2—C3—C4—C5	177.72 (17)	C2A—C3A—C4A—C5A	177.00 (18)
C13—C3—C4—C5	−2.3 (3)	C13A—C3A—C4A—C5A	−4.0 (3)
C2—C3—C4—C10	−0.4 (2)	C2A—C3A—C4A—C10A	−1.4 (2)
C13—C3—C4—C10	179.51 (18)	C13A—C3A—C4A—C10A	177.65 (18)
C3—C4—C5—C6	−177.32 (19)	C3A—C4A—C5A—C6A	−177.74 (18)
C10—C4—C5—C6	0.4 (3)	C10A—C4A—C5A—C6A	0.3 (3)
C4—C5—C6—C7	1.3 (3)	C4A—C5A—C6A—C7A	−0.3 (3)
C5—C6—C7—C8	−0.6 (4)	C5A—C6A—C7A—C8A	1.2 (3)
C6—C7—C8—C9	−1.1 (4)	C6A—C7A—C8A—C9A	−1.5 (3)
C7—C8—C9—C10	0.9 (4)	C7A—C8A—C9A—C10A	0.4 (3)
C8—C9—C10—C1	177.52 (19)	C8A—C9A—C10A—C1A	177.21 (18)
C8—C9—C10—C4	1.1 (3)	C8A—C9A—C10A—C4A	0.9 (3)
C2—C1—C10—C9	−175.17 (18)	C2A—C1A—C10A—C9A	−176.37 (17)
C11—C1—C10—C9	4.1 (3)	C11A—C1A—C10A—C9A	2.2 (3)
C2—C1—C10—C4	1.8 (2)	C2A—C1A—C10A—C4A	0.6 (2)
C11—C1—C10—C4	−178.89 (18)	C11A—C1A—C10A—C4A	179.14 (17)
C5—C4—C10—C9	−2.0 (3)	C5A—C4A—C10A—C9A	−1.0 (3)
C3—C4—C10—C9	176.06 (18)	C3A—C4A—C10A—C9A	177.34 (18)
C5—C4—C10—C1	−178.95 (18)	C5A—C4A—C10A—C1A	−177.85 (18)
C3—C4—C10—C1	−0.9 (2)	C3A—C4A—C10A—C1A	0.47 (19)
C2—C1—C11—O1	−171.8 (2)	C2A—C1A—C11A—O1A	−168.50 (19)
C10—C1—C11—O1	9.0 (3)	C10A—C1A—C11A—O1A	13.2 (3)
C2—C1—C11—C12	9.7 (3)	C2A—C1A—C11A—C12A	13.2 (3)
C10—C1—C11—C12	−169.47 (18)	C10A—C1A—C11A—C12A	−165.03 (17)
O1—C11—C12—F2	3.9 (3)	O1A—C11A—C12A—F2A	−1.3 (3)
C1—C11—C12—F2	−177.52 (17)	C1A—C11A—C12A—F2A	177.14 (16)
O1—C11—C12—F1	−115.7 (2)	O1A—C11A—C12A—F1A	−120.81 (19)
C1—C11—C12—F1	62.9 (2)	C1A—C11A—C12A—F1A	57.6 (2)
O1—C11—C12—F3	124.1 (2)	O1A—C11A—C12A—F3A	118.75 (19)
C1—C11—C12—F3	−57.2 (2)	C1A—C11A—C12A—F3A	−62.8 (2)
C2—C3—C13—O2	168.8 (2)	C2A—C3A—C13A—O2A	175.72 (19)
C4—C3—C13—O2	−11.1 (3)	C4A—C3A—C13A—O2A	−3.1 (3)
C2—C3—C13—C14	−10.9 (3)	C2A—C3A—C13A—C14A	−4.6 (3)
C4—C3—C13—C14	169.21 (17)	C4A—C3A—C13A—C14A	176.51 (17)
O2—C13—C14—F6	6.2 (3)	O2A—C13A—C14A—F6A	0.0 (3)
C3—C13—C14—F6	−174.04 (16)	C3A—C13A—C14A—F6A	−179.65 (17)
O2—C13—C14—F5	−113.9 (2)	O2A—C13A—C14A—F4A	120.0 (2)
C3—C13—C14—F5	65.9 (2)	C3A—C13A—C14A—F4A	−59.6 (2)
O2—C13—C14—F4	126.63 (19)	O2A—C13A—C14A—F5A	−120.6 (2)
C3—C13—C14—F4	−53.7 (2)	C3A—C13A—C14A—F5A	59.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F3	0.95	2.40	2.916 (2)	114
C2A—H2A···F3A	0.95	2.45	2.972 (2)	115
C2A—H2A···F5A	0.95	2.50	2.968 (2)	111
C5—H5···O2	0.95	2.31	2.988 (2)	127
C5A—H5A···O2A	0.95	2.33	3.001 (2)	127
C6—H6···O2Aⁱ	0.95	2.52	3.236 (2)	133
C6A—H6A···O2ⁱ	0.95	2.47	3.160 (2)	130
C8—H8···F2Aⁱⁱ	0.95	2.45	3.358 (2)	160
C9—H9···O1	0.95	2.31	2.983 (2)	127
C9—H9···O1Aⁱⁱ	0.95	2.58	3.454 (2)	153
C9A—H9A···O1ⁱⁱ	0.95	2.50	3.352 (2)	149
C9A—H9A···O1A	0.95	2.31	2.993 (2)	128

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₆F₆O₂
M_r	320.19
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.1634 (2), 10.8681 (4), 16.3286 (5)
α, β, γ (°)	81.544 (2), 83.310 (2), 80.009 (2)
V (Å³)	1232.92 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.40 × 0.14 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.933, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	20089, 5321, 3680
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.02
No. of reflections	5321
No. of parameters	397
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.31

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F3	0.95	2.40	2.916 (2)	114
C2A—H2A···F3A	0.95	2.45	2.972 (2)	115
C2A—H2A···F5A	0.95	2.50	2.968 (2)	111
C5—H5···O2	0.95	2.31	2.988 (2)	127
C5A—H5A···O2A	0.95	2.33	3.001 (2)	127
C6—H6···O2Aⁱ	0.95	2.52	3.236 (2)	133
C6A—H6A···O2ⁱ	0.95	2.47	3.160 (2)	130
C8—H8···F2Aⁱⁱ	0.95	2.45	3.358 (2)	160
C9—H9···O1	0.95	2.31	2.983 (2)	127
C9—H9···O1Aⁱⁱ	0.95	2.58	3.454 (2)	153
C9A—H9A···O1ⁱⁱ	0.95	2.50	3.352 (2)	149
C9A—H9A···O1A	0.95	2.31	2.993 (2)	128

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+2, −z+1.

Acknowledgements

This work was performed within the Cluster of Excellence `Structure Design of Novel High-Performance Materials via Atomic Design and Defect Engineering (ADDE)', which is supported financially by the European Union (European Regional Development Fund) and by the Ministry of Science and Art of Saxony (SMWK).

References

Brammer, L., Bruton, E. A. & Sherwood, P. (2001). Cryst. Growth Des. 1, 277–290. Web of Science CrossRef CAS Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mathias, L. J. & Overberger, C. G. (1980). J. Org. Chem. 45, 1701–1703. CrossRef CAS Google Scholar
Metrangolo, P., Resnati, G., Pilati, T. & Biella, S. (2008). Halogen Bonding, Structure and Bonding, Vol. 126, edited by P. Metrangolo & G. Resnati, pp. 105–136. Berlin, Heidelberg: Springer. Google Scholar
Robertson, J. M., Shearer, H. M. M., Sim, G. A. & Watson, D. G. (1962). Acta Cryst. 15, 1–8. CSD CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zielinski, T., Kedziorek, M. & Jurczak, J. (2008). Chem. Eur. J. 14, 838–846. PubMed Google Scholar