2,2,2-Trifluoro-1-[3-(2,2,2-trifluoro-acet-yl)azulen-1-yl]ethanone.

There are two mol-ecules in the asymmetric unit of the title compound, C(14)H(6)F(6)O(2), 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 inter-molecular C-H⋯O and C-H⋯F inter-actions, 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 = 320.19

Triclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.02

5321 reflections

397 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.31 e Å−3

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) ▶.

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

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

Supplementary material file. DOI: 10.1107/S1600536811017569/im2284Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811017569/im2284Isup4.cml

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

C14H6F6O2	Z = 4
Mr = 320.19	F(000) = 640
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0465P)2 + 0.5715P] where P = (Fo2 + 2Fc2)/3
5321 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.31 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
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)

	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)

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)

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

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) ; (ii) .