A 1:1 cocrystal of 2,8-bis­(trifluoro­methyl)quinolin-4-ol and 2,8-bis­(tri­fluoro­meth­yl)quinolin-4(1H)-one

Sarojini, B.K.; Narayana, B.; Mayekar, A.N.; Yathirajan, H.S.; Bolte, M.

doi:10.1107/S1600536807053482

A 1:1 cocrystal of 2,8-bis(trifluoromethyl)quinolin-4-ol and 2,8-bis(trifluoromethyl)quinolin-4(1H)-one

B. K. Sarojini, B. Narayana, A. N. Mayekar, H. S. Yathirajan and M. Bolte

In the title compound, C₁₁H₅F₆NO·C₁₁H₅F₆NO, both molecules (except F and H atoms) are essentially planar (the r.m.s. deviations for all non-H atoms are 0.008 and 0.034 Å for the alcohol and ketone, respectively). The two molecules are connected by an O—H

O hydrogen bond. The protonated N atom is shielded and therefore does not form a hydrogen bond. The F atoms of one trifluoromethyl group are disordered over two positions; the site occupancy factors are 0.88 and 0.12.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053482/at2454sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053482/at2454Isup2.hkl Contains datablock I

CCDC reference: 667474

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.055
wR factor = 0.144
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  F2A    ..  F1'     ..       2.58 Ang.
PLAT431_ALERT_2_B Short Inter HL..A Contact  F4A    ..  F3'     ..       2.54 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT213_ALERT_2_C Atom F1A     has ADP max/min Ratio .............       3.60 prola
PLAT220_ALERT_2_C Large Non-Solvent    F     Ueq(max)/Ueq(min) ...       3.39 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C11A
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.10 Deg.
              C11  -F2'  -F3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.80 Deg.
              C11  -F3'  -F2'     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

It is well known that the quinoline ring system is an important structural unit widely existing in alkaloids, therapeutics and synthetic analogues with interesting biological activities. A large variety of quinoline derivatives have been used as antimalarial, anti-inflammatory agents, antiasthmatic, antibacterial, antihypertensive and tyrokinase PDGF-RTK inhibiting agents (El-Masry et al., 2000; Roma et al., 2000; Zhang & Jenekhe, 2000; Maguire et al., 1994). Furthermore, poly-substituted quinolines have been found to undergo hierarchical self-assembly into a variety of nano- and mesostructures with enhanced electronic and photonic functions. Quinoline antimalarial drugs, such as chloroquine, quinine and amodiaquine have been used as effective treatments for malaria (Tilley et al., 2001). Until the onset of parasite resistance, chloroquine was especially valuable, owing to its affordability, limited toxicity and potency. It is believed to accumulate in its diprotonated state in the acidic environment of the Plasmodium food vacuole in an infected red blood cell, unable to re-cross the lipid membrane. The drug activity is understood to arise from complex formation between the 4-aminoquinoline drug and its target, haematin, thus preventing the haematin from aggregating to crystalline haemozoin (Egan et al., 1994). This class of compounds form complexes with haematin and prevents its aggregation to crystalline haemozoin, complexes between the drug molecule and haematin are notoriously diffcult to crystallize. The structures of 4-chloro-8-(trifluoromethyl)quinoline (Yathirajan, Sreevidya, Prathap et al., 2007), bis{4-[(2-hydroxybenzylidine)hydrazino]-8-(trifluoromethyl)quinolinium} sulfate tetrahydrate (Yathirajan, Sarojini, Narayana et al., 2007), 1-(quinolin-2-yl)ethanone (Butcher et al., 2007), 2-phenylquinoline 1-oxide (Fahlquist et al., 2006). Three 4-aminoquinolines (Bourne et al., 2006) have been published. In view of the importance of quinoline derivatives, we report the crystal structure of a new quinoline derivative, (I) which actually a mixture of hydrogen bonded 2,8-bis(trifluoromethyl)quinolin-4-ol and 2,8-bis(trifluoromethyl)quinolin-4(1H)-one.

The title co-crystal contains 2,8-bis(trifluoromethyl)quinolin-4-ol [C₁₁H₅F₆NO], and 2,8-bis(trifluoromethyl)quinolin-4(1H)-one [C₁₁H₅F₆NO]. Both molecules (except F and H atoms) are essentially planar [r.m.s. deviation for all non-H atoms 0.008 Å and 0.034 Å for 2,8-bis(trifluoromethyl)quinolin-4-ol and 2,8-bis(trifluoromethyl)quinolin-4(1H)-one, respectively]. The two molecules are connected by a O—H···O hydrogen bond. The protonated N atom is shielded and therefore does not form a hydrogen bond.

Related literature top

For related literature, see: Bourne et al. (2006); Butcher et al. (2007); Egan et al. (1994); El-Masry et al. (2000); Fahlquist et al. (2006); Maguire et al. (1994); Roma et al. (2000); Tilley et al. (2001); Yathirajan, Sarojini et al. (2007); Yathirajan, Sreevidya et al. (2007); Zhang & Jenekhe (2000).

Experimental top

The title compound was obtained from SeQuent Scientific Ltd, Mangalore, as a gift sample and was crystallized from acetone [m.p.: 391–395 K].

Structure description top

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. For clarity, the major component with atoms F1, F2 and F3, of the disordered CF₃ group is shown.

2,8-bis(trifluoromethyl)quinolin-4-ol– 2,8-bis(trifluoromethyl)quinolin-4(1H)-one (1/1) top

Crystal data top

C₁₁H₅F₆NO·C₁₁H₅F₆NO	F(000) = 1120
M_r = 562.32	D_x = 1.699 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25632 reflections
a = 9.1868 (4) Å	θ = 3.4–27.6°
b = 13.9634 (8) Å	µ = 0.18 mm⁻¹
c = 17.1928 (8) Å	T = 173 K
β = 94.687 (4)°	Block, colourless
V = 2198.10 (19) Å³	0.34 × 0.29 × 0.21 mm
Z = 4

Data collection top

Stoe IPDSII two-circle diffractometer	3976 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 27.6°, θ_min = 3.5°
ω scans	h = −11→11
32900 measured reflections	k = −18→18
5055 independent reflections	l = −22→22

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.063P)² + 1.036P] where P = (F_o² + 2F_c²)/3
5055 reflections	(Δ/σ)_max < 0.001
364 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₁H₅F₆NO·C₁₁H₅F₆NO	V = 2198.10 (19) Å³
M_r = 562.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1868 (4) Å	µ = 0.18 mm⁻¹
b = 13.9634 (8) Å	T = 173 K
c = 17.1928 (8) Å	0.34 × 0.29 × 0.21 mm
β = 94.687 (4)°

Data collection top

Stoe IPDSII two-circle diffractometer	3976 reflections with I > 2σ(I)
32900 measured reflections	R_int = 0.046
5055 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.50 e Å⁻³
5055 reflections	Δρ_min = −0.40 e Å⁻³
364 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)
F1	0.6119 (4)	0.10065 (17)	0.66836 (11)	0.1030 (13)	0.884 (4)
F2	0.5877 (3)	−0.01257 (14)	0.58753 (12)	0.0726 (7)	0.884 (4)
F3	0.7957 (2)	0.04131 (19)	0.61350 (14)	0.0849 (9)	0.884 (4)
F1'	0.7539 (16)	0.1174 (10)	0.6622 (8)	0.057 (4)*	0.116 (4)
F2'	0.5544 (18)	0.0447 (13)	0.6319 (10)	0.068 (5)*	0.116 (4)
F3'	0.707 (2)	−0.0044 (13)	0.5915 (10)	0.071 (5)*	0.116 (4)
F4	0.74374 (17)	−0.02462 (10)	0.34336 (10)	0.0573 (4)
F5	0.8738 (2)	0.04206 (13)	0.26057 (9)	0.0688 (5)
F6	0.93313 (16)	0.05552 (11)	0.38408 (9)	0.0541 (4)
O1	0.4403 (2)	0.35464 (12)	0.47983 (12)	0.0564 (5)
N1	0.69448 (19)	0.11665 (12)	0.47114 (10)	0.0314 (4)
H1	0.750 (3)	0.067 (2)	0.4707 (16)	0.049 (7)*
C2	0.6335 (2)	0.14076 (14)	0.53776 (12)	0.0332 (4)
C3	0.5485 (2)	0.21923 (16)	0.54371 (14)	0.0396 (5)
H3	0.5089	0.2334	0.5917	0.047*
C4	0.5180 (2)	0.28136 (15)	0.47720 (15)	0.0402 (5)
C5	0.5811 (2)	0.25282 (14)	0.40537 (13)	0.0357 (4)
C6	0.5528 (3)	0.30743 (16)	0.33642 (15)	0.0465 (6)
H6	0.4943	0.3635	0.3373	0.056*
C7	0.6091 (3)	0.28020 (18)	0.26844 (16)	0.0522 (6)
H7	0.5885	0.3170	0.2224	0.063*
C8	0.6970 (3)	0.19818 (18)	0.26646 (14)	0.0468 (5)
H8	0.7355	0.1798	0.2190	0.056*
C9	0.7281 (2)	0.14387 (15)	0.33295 (12)	0.0353 (4)
C10	0.6693 (2)	0.17045 (13)	0.40361 (12)	0.0309 (4)
C11	0.6610 (3)	0.07092 (16)	0.60443 (13)	0.0405 (5)
C12	0.8194 (3)	0.05538 (16)	0.32928 (13)	0.0404 (5)
F1A	0.3274 (3)	0.5647 (3)	0.29670 (13)	0.1443 (14)
F2A	0.2343 (2)	0.70616 (15)	0.29298 (10)	0.0827 (6)
F3A	0.1012 (2)	0.58500 (14)	0.26504 (9)	0.0748 (5)
F4A	−0.21334 (16)	0.85612 (10)	0.51026 (9)	0.0543 (4)
F5A	−0.02372 (15)	0.85788 (9)	0.44455 (9)	0.0512 (4)
F6A	−0.20327 (14)	0.76233 (9)	0.41182 (7)	0.0425 (3)
O1A	0.2846 (2)	0.46104 (12)	0.57062 (11)	0.0495 (4)
H1A	0.341 (4)	0.426 (3)	0.543 (2)	0.082 (12)*
N1A	0.08353 (19)	0.66696 (12)	0.42119 (10)	0.0338 (4)
C2A	0.1814 (2)	0.60571 (16)	0.39848 (13)	0.0379 (5)
C3A	0.2539 (2)	0.53454 (15)	0.44419 (14)	0.0394 (5)
H3A	0.3229	0.4934	0.4229	0.047*
C4A	0.2224 (2)	0.52599 (14)	0.52074 (13)	0.0367 (5)
C5A	0.1184 (2)	0.58982 (14)	0.54984 (12)	0.0330 (4)
C6A	0.0808 (3)	0.58667 (16)	0.62811 (13)	0.0435 (5)
H6A	0.1258	0.5408	0.6631	0.052*
C7A	−0.0192 (3)	0.64892 (19)	0.65348 (14)	0.0504 (6)
H7A	−0.0441	0.6458	0.7060	0.060*
C8A	−0.0864 (3)	0.71823 (17)	0.60235 (13)	0.0430 (5)
H8A	−0.1559	0.7612	0.6208	0.052*
C9A	−0.0521 (2)	0.72396 (14)	0.52660 (12)	0.0327 (4)
C10A	0.0518 (2)	0.65905 (13)	0.49738 (11)	0.0294 (4)
C11A	0.2134 (3)	0.6153 (2)	0.31353 (16)	0.0562 (7)
C12A	−0.1217 (2)	0.79917 (15)	0.47330 (13)	0.0375 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.208 (3)	0.0682 (14)	0.0386 (11)	0.0600 (18)	0.0466 (15)	0.0101 (10)
F2	0.0940 (17)	0.0544 (11)	0.0674 (13)	−0.0245 (10)	−0.0054 (11)	0.0189 (10)
F3	0.0376 (10)	0.119 (2)	0.0972 (17)	0.0134 (11)	0.0032 (10)	0.0760 (15)
F4	0.0614 (9)	0.0341 (7)	0.0777 (11)	−0.0009 (6)	0.0134 (8)	−0.0042 (7)
F5	0.0832 (12)	0.0799 (11)	0.0468 (9)	0.0208 (9)	0.0264 (8)	0.0021 (8)
F6	0.0453 (8)	0.0533 (8)	0.0618 (9)	0.0160 (6)	−0.0068 (7)	−0.0074 (7)
O1	0.0496 (10)	0.0402 (9)	0.0782 (13)	0.0213 (8)	−0.0013 (9)	−0.0024 (8)
N1	0.0308 (8)	0.0295 (8)	0.0338 (9)	0.0074 (7)	0.0017 (7)	0.0032 (6)
C2	0.0297 (9)	0.0340 (10)	0.0355 (10)	0.0036 (8)	0.0013 (8)	−0.0001 (8)
C3	0.0348 (11)	0.0392 (11)	0.0445 (12)	0.0089 (8)	0.0023 (9)	−0.0045 (9)
C4	0.0298 (10)	0.0310 (10)	0.0584 (14)	0.0059 (8)	−0.0052 (9)	−0.0023 (9)
C5	0.0304 (10)	0.0279 (9)	0.0472 (12)	0.0001 (7)	−0.0073 (8)	0.0036 (8)
C6	0.0448 (12)	0.0327 (10)	0.0594 (15)	0.0031 (9)	−0.0122 (11)	0.0118 (10)
C7	0.0594 (15)	0.0449 (13)	0.0500 (14)	−0.0024 (11)	−0.0106 (12)	0.0189 (11)
C8	0.0524 (14)	0.0484 (13)	0.0389 (12)	−0.0061 (11)	−0.0013 (10)	0.0117 (10)
C9	0.0353 (10)	0.0341 (10)	0.0360 (11)	−0.0034 (8)	−0.0001 (8)	0.0060 (8)
C10	0.0259 (9)	0.0285 (9)	0.0370 (10)	−0.0021 (7)	−0.0045 (7)	0.0041 (7)
C11	0.0432 (12)	0.0404 (11)	0.0391 (11)	0.0078 (9)	0.0108 (9)	0.0041 (9)
C12	0.0423 (12)	0.0435 (11)	0.0358 (11)	0.0010 (9)	0.0059 (9)	−0.0005 (9)
F1A	0.124 (2)	0.244 (3)	0.0723 (14)	0.132 (2)	0.0543 (14)	0.0448 (17)
F2A	0.1043 (15)	0.0947 (14)	0.0513 (10)	−0.0278 (12)	0.0199 (10)	0.0103 (9)
F3A	0.1025 (14)	0.0797 (12)	0.0410 (9)	0.0030 (10)	−0.0013 (9)	−0.0131 (8)
F4A	0.0539 (8)	0.0489 (8)	0.0596 (9)	0.0237 (7)	0.0024 (7)	−0.0143 (7)
F5A	0.0451 (7)	0.0335 (7)	0.0742 (10)	0.0015 (6)	0.0006 (7)	0.0149 (6)
F6A	0.0413 (7)	0.0430 (7)	0.0418 (7)	0.0081 (5)	−0.0045 (5)	−0.0041 (5)
O1A	0.0580 (11)	0.0344 (8)	0.0537 (10)	0.0143 (7)	−0.0101 (8)	0.0056 (7)
N1A	0.0320 (8)	0.0350 (8)	0.0345 (9)	0.0059 (7)	0.0024 (7)	0.0006 (7)
C2A	0.0359 (11)	0.0404 (11)	0.0372 (11)	0.0089 (9)	0.0018 (8)	−0.0013 (9)
C3A	0.0356 (11)	0.0344 (10)	0.0474 (13)	0.0099 (8)	−0.0007 (9)	−0.0047 (9)
C4A	0.0374 (10)	0.0255 (9)	0.0450 (12)	0.0022 (8)	−0.0094 (9)	−0.0002 (8)
C5A	0.0344 (10)	0.0274 (9)	0.0361 (10)	−0.0023 (7)	−0.0043 (8)	−0.0006 (7)
C6A	0.0543 (13)	0.0386 (11)	0.0362 (12)	−0.0035 (10)	−0.0042 (10)	0.0060 (9)
C7A	0.0638 (16)	0.0553 (14)	0.0326 (12)	−0.0005 (12)	0.0074 (11)	0.0004 (10)
C8A	0.0471 (12)	0.0435 (12)	0.0392 (12)	0.0021 (10)	0.0081 (10)	−0.0083 (9)
C9A	0.0328 (10)	0.0284 (9)	0.0365 (10)	0.0002 (7)	0.0012 (8)	−0.0044 (8)
C10A	0.0291 (9)	0.0260 (9)	0.0327 (10)	−0.0014 (7)	−0.0006 (7)	−0.0018 (7)
C11A	0.0525 (15)	0.0713 (17)	0.0462 (14)	0.0241 (13)	0.0118 (12)	0.0061 (12)
C12A	0.0343 (10)	0.0326 (10)	0.0453 (12)	0.0064 (8)	0.0019 (9)	−0.0060 (9)

Geometric parameters (Å, º) top

F1—C11	1.290 (3)	C9—C10	1.419 (3)
F2—C11	1.366 (3)	C9—C12	1.498 (3)
F3—C11	1.302 (3)	F1A—C11A	1.316 (3)
F1'—C11	1.413 (14)	F2A—C11A	1.335 (4)
F2'—C11	1.180 (16)	F3A—C11A	1.340 (4)
F2'—F3'	1.76 (2)	F4A—C12A	1.354 (2)
F3'—C11	1.163 (17)	F5A—C12A	1.341 (3)
F4—C12	1.348 (3)	F6A—C12A	1.347 (2)
F5—C12	1.332 (3)	O1A—C4A	1.343 (3)
F6—C12	1.348 (3)	O1A—H1A	0.87 (4)
O1—C4	1.250 (3)	N1A—C2A	1.323 (3)
N1—C2	1.358 (3)	N1A—C10A	1.369 (3)
N1—C10	1.386 (3)	C2A—C3A	1.401 (3)
N1—H1	0.86 (3)	C2A—C11A	1.519 (3)
C2—C3	1.354 (3)	C3A—C4A	1.376 (3)
C2—C11	1.510 (3)	C3A—H3A	0.9500
C3—C4	1.444 (3)	C4A—C5A	1.427 (3)
C3—H3	0.9500	C5A—C6A	1.417 (3)
C4—C5	1.462 (3)	C5A—C10A	1.425 (3)
C5—C10	1.408 (3)	C6A—C7A	1.362 (4)
C5—C6	1.416 (3)	C6A—H6A	0.9500
C6—C7	1.370 (4)	C7A—C8A	1.415 (3)
C6—H6	0.9500	C7A—H7A	0.9500
C7—C8	1.403 (4)	C8A—C9A	1.367 (3)
C7—H7	0.9500	C8A—H8A	0.9500
C8—C9	1.382 (3)	C9A—C10A	1.436 (3)
C8—H8	0.9500	C9A—C12A	1.502 (3)

C11—F2'—F3'	41.1 (8)	F5—C12—C9	113.85 (19)
C11—F3'—F2'	41.8 (8)	F4—C12—C9	112.15 (18)
C2—N1—C10	121.32 (17)	F6—C12—C9	111.96 (18)
C2—N1—H1	119.5 (18)	C4A—O1A—H1A	106 (2)
C10—N1—H1	119.1 (18)	C2A—N1A—C10A	115.66 (17)
C3—C2—N1	123.0 (2)	N1A—C2A—C3A	126.6 (2)
C3—C2—C11	121.78 (19)	N1A—C2A—C11A	114.60 (19)
N1—C2—C11	115.16 (17)	C3A—C2A—C11A	118.78 (19)
C2—C3—C4	120.1 (2)	C4A—C3A—C2A	118.08 (19)
C2—C3—H3	119.9	C4A—C3A—H3A	121.0
C4—C3—H3	119.9	C2A—C3A—H3A	121.0
O1—C4—C3	122.5 (2)	O1A—C4A—C3A	123.9 (2)
O1—C4—C5	121.4 (2)	O1A—C4A—C5A	117.4 (2)
C3—C4—C5	116.11 (18)	C3A—C4A—C5A	118.71 (18)
C10—C5—C6	119.2 (2)	C6A—C5A—C10A	119.80 (19)
C10—C5—C4	120.62 (19)	C6A—C5A—C4A	122.38 (19)
C6—C5—C4	120.1 (2)	C10A—C5A—C4A	117.82 (19)
C7—C6—C5	120.6 (2)	C7A—C6A—C5A	120.5 (2)
C7—C6—H6	119.7	C7A—C6A—H6A	119.8
C5—C6—H6	119.7	C5A—C6A—H6A	119.8
C6—C7—C8	120.3 (2)	C6A—C7A—C8A	120.6 (2)
C6—C7—H7	119.8	C6A—C7A—H7A	119.7
C8—C7—H7	119.8	C8A—C7A—H7A	119.7
C9—C8—C7	120.5 (2)	C9A—C8A—C7A	120.6 (2)
C9—C8—H8	119.7	C9A—C8A—H8A	119.7
C7—C8—H8	119.7	C7A—C8A—H8A	119.7
C8—C9—C10	119.8 (2)	C8A—C9A—C10A	120.51 (19)
C8—C9—C12	119.8 (2)	C8A—C9A—C12A	120.16 (19)
C10—C9—C12	120.38 (18)	C10A—C9A—C12A	119.32 (18)
N1—C10—C5	118.78 (19)	N1A—C10A—C5A	123.11 (17)
N1—C10—C9	121.75 (18)	N1A—C10A—C9A	118.88 (17)
C5—C10—C9	119.46 (18)	C5A—C10A—C9A	118.00 (18)
F3'—C11—F2'	97.1 (13)	F1A—C11A—F2A	108.5 (3)
F1—C11—F3	113.3 (3)	F1A—C11A—F3A	106.2 (3)
F1—C11—F2	104.8 (2)	F2A—C11A—F3A	104.8 (2)
F3—C11—F2	101.6 (2)	F1A—C11A—C2A	112.6 (2)
F3'—C11—F1'	109.9 (11)	F2A—C11A—C2A	112.4 (2)
F2'—C11—F1'	109.6 (11)	F3A—C11A—C2A	111.8 (2)
F1—C11—C2	112.97 (19)	F5A—C12A—F6A	106.93 (18)
F3—C11—C2	113.21 (18)	F5A—C12A—F4A	106.00 (17)
F2—C11—C2	109.93 (19)	F6A—C12A—F4A	105.37 (16)
F1'—C11—C2	106.9 (6)	F5A—C12A—C9A	112.78 (17)
F5—C12—F4	106.24 (19)	F6A—C12A—C9A	113.19 (17)
F5—C12—F6	107.15 (19)	F4A—C12A—C9A	111.99 (18)
F4—C12—F6	104.91 (19)

C10—N1—C2—C3	−1.9 (3)	C3—C2—C11—F1'	−71.5 (7)
C10—N1—C2—C11	175.22 (18)	N1—C2—C11—F1'	111.4 (7)
N1—C2—C3—C4	0.5 (3)	C8—C9—C12—F5	5.5 (3)
C11—C2—C3—C4	−176.4 (2)	C10—C9—C12—F5	−176.58 (19)
C2—C3—C4—O1	−179.9 (2)	C8—C9—C12—F4	−115.1 (2)
C2—C3—C4—C5	1.2 (3)	C10—C9—C12—F4	62.8 (3)
O1—C4—C5—C10	179.5 (2)	C8—C9—C12—F6	127.3 (2)
C3—C4—C5—C10	−1.6 (3)	C10—C9—C12—F6	−54.9 (3)
O1—C4—C5—C6	−1.1 (3)	C10A—N1A—C2A—C3A	0.3 (3)
C3—C4—C5—C6	177.8 (2)	C10A—N1A—C2A—C11A	179.4 (2)
C10—C5—C6—C7	0.7 (3)	N1A—C2A—C3A—C4A	−0.1 (4)
C4—C5—C6—C7	−178.7 (2)	C11A—C2A—C3A—C4A	−179.2 (2)
C5—C6—C7—C8	−0.7 (4)	C2A—C3A—C4A—O1A	−179.8 (2)
C6—C7—C8—C9	−0.1 (4)	C2A—C3A—C4A—C5A	−0.2 (3)
C7—C8—C9—C10	0.8 (3)	O1A—C4A—C5A—C6A	0.4 (3)
C7—C8—C9—C12	178.7 (2)	C3A—C4A—C5A—C6A	−179.3 (2)
C2—N1—C10—C5	1.4 (3)	O1A—C4A—C5A—C10A	179.95 (18)
C2—N1—C10—C9	−177.64 (19)	C3A—C4A—C5A—C10A	0.3 (3)
C6—C5—C10—N1	−179.02 (19)	C10A—C5A—C6A—C7A	0.5 (3)
C4—C5—C10—N1	0.3 (3)	C4A—C5A—C6A—C7A	−180.0 (2)
C6—C5—C10—C9	0.1 (3)	C5A—C6A—C7A—C8A	−0.5 (4)
C4—C5—C10—C9	179.42 (18)	C6A—C7A—C8A—C9A	0.0 (4)
C8—C9—C10—N1	178.3 (2)	C7A—C8A—C9A—C10A	0.6 (3)
C12—C9—C10—N1	0.4 (3)	C7A—C8A—C9A—C12A	−178.7 (2)
C8—C9—C10—C5	−0.8 (3)	C2A—N1A—C10A—C5A	−0.1 (3)
C12—C9—C10—C5	−178.66 (19)	C2A—N1A—C10A—C9A	179.19 (18)
F2'—F3'—C11—F1	48.0 (11)	C6A—C5A—C10A—N1A	179.41 (19)
F2'—F3'—C11—F3	139.3 (10)	C4A—C5A—C10A—N1A	−0.2 (3)
F2'—F3'—C11—F2	−29.6 (12)	C6A—C5A—C10A—C9A	0.1 (3)
F2'—F3'—C11—F1'	113.9 (11)	C4A—C5A—C10A—C9A	−179.48 (17)
F2'—F3'—C11—C2	−122.7 (11)	C8A—C9A—C10A—N1A	−180.0 (2)
F3'—F2'—C11—F1	−132.7 (10)	C12A—C9A—C10A—N1A	−0.7 (3)
F3'—F2'—C11—F3	−43.1 (12)	C8A—C9A—C10A—C5A	−0.6 (3)
F3'—F2'—C11—F2	28.4 (11)	C12A—C9A—C10A—C5A	178.67 (18)
F3'—F2'—C11—F1'	−114.1 (12)	N1A—C2A—C11A—F1A	169.4 (3)
F3'—F2'—C11—C2	126.0 (10)	C3A—C2A—C11A—F1A	−11.4 (4)
C3—C2—C11—F3'	163.7 (12)	N1A—C2A—C11A—F2A	46.5 (3)
N1—C2—C11—F3'	−13.5 (12)	C3A—C2A—C11A—F2A	−134.4 (2)
C3—C2—C11—F2'	50.0 (11)	N1A—C2A—C11A—F3A	−71.1 (3)
N1—C2—C11—F2'	−127.2 (11)	C3A—C2A—C11A—F3A	108.1 (3)
C3—C2—C11—F1	−8.4 (4)	C8A—C9A—C12A—F5A	120.6 (2)
N1—C2—C11—F1	174.4 (3)	C10A—C9A—C12A—F5A	−58.7 (2)
C3—C2—C11—F3	−138.9 (3)	C8A—C9A—C12A—F6A	−117.8 (2)
N1—C2—C11—F3	44.0 (3)	C10A—C9A—C12A—F6A	62.9 (2)
C3—C2—C11—F2	108.2 (2)	C8A—C9A—C12A—F4A	1.1 (3)
N1—C2—C11—F2	−68.9 (3)	C10A—C9A—C12A—F4A	−178.17 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1	0.87 (4)	1.78 (4)	2.656 (3)	174 (4)

Experimental details

Crystal data
Chemical formula	C₁₁H₅F₆NO·C₁₁H₅F₆NO
M_r	562.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.1868 (4), 13.9634 (8), 17.1928 (8)
β (°)	94.687 (4)
V (Å³)	2198.10 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.34 × 0.29 × 0.21

Data collection
Diffractometer	Stoe IPDSII two-circle
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	32900, 5055, 3976
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.144, 1.14
No. of reflections	5055
No. of parameters	364
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.40

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).