Benzyl 2-{[2,8-bis-(trifluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidine-1-carboxyl-ate.

The title mol-ecule, C(25)H(22)F(6)N(2)O(3), adopts an open conformation whereby the quinoline and carboxyl-ate ester groups are orientated in opposite directions but to the same side of the piperidine ring so that the mol-ecule has an approximate U-shape. The piperidine ring adopts a distorted boat conformation. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R(2) (2)(14) loops.

Related literature

For background to the anti-mycobacterial activity of mefloquine, see: Gonçalves et al. (2010 ▶); Mao et al. (2007 ▶); Maguire et al. (2006 ▶). For the synthesis, see: Grellepois et al. (2005 ▶). For related structures, see: Gonçalves et al. (2011a ▶,b ▶); Wardell et al. (2010 ▶, 2011a ▶,b ▶); Pitaluga et al. (2010 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C25H22F6N2O3

M = 512.45

Monoclinic,

a = 12.7793 (5) Å

b = 13.9970 (7) Å

c = 13.2188 (9) Å

β = 109.999 (8)°

V = 2221.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.15 × 0.11 × 0.04 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ▶) T min = 0.757, T max = 1.000

10271 measured reflections

5060 independent reflections

4132 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.00

5060 reflections

328 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811047738/hb6498sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047738/hb6498Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047738/hb6498Isup3.cml

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

C25H22F6N2O3	F(000) = 1056
Mr = 512.45	Dx = 1.532 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8584 reflections
a = 12.7793 (5) Å	θ = 3.1–27.5°
b = 13.9970 (7) Å	µ = 0.13 mm−1
c = 13.2188 (9) Å	T = 100 K
β = 109.999 (8)°	Plate, colourless
V = 2221.9 (2) Å3	0.15 × 0.11 × 0.04 mm
Z = 4

Rigaku Saturn724+ diffractometer	5060 independent reflections
Radiation source: Rotating Anode	4132 reflections with I > 2σ(I)
Confocal	Rint = 0.026
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.1°
profile data from ω–scans	h = −15→16
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	k = −15→18
Tmin = 0.757, Tmax = 1.000	l = −14→17
10271 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.9076P] where P = (Fo2 + 2Fc2)/3
5060 reflections	(Δ/σ)max < 0.001
328 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.32 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.06301 (8)	0.63866 (8)	0.42728 (8)	0.0347 (3)
F2	0.08200 (10)	0.59309 (10)	0.27995 (8)	0.0472 (3)
F3	0.00983 (8)	0.49890 (9)	0.36550 (11)	0.0490 (3)
F4	0.24269 (7)	0.32103 (7)	0.22775 (7)	0.0244 (2)
F5	0.40411 (8)	0.31616 (7)	0.21097 (7)	0.0268 (2)
F6	0.32339 (7)	0.45128 (7)	0.20711 (7)	0.0223 (2)
O1	0.34838 (8)	0.58357 (7)	0.75929 (8)	0.0177 (2)
H1o	0.3897 (13)	0.6035 (13)	0.8197 (10)	0.026*
O2	0.54803 (8)	0.32514 (8)	0.88013 (8)	0.0172 (2)
O3	0.53313 (8)	0.33958 (7)	1.04525 (8)	0.0167 (2)
N1	0.24628 (9)	0.47056 (9)	0.38278 (9)	0.0148 (2)
N2	0.40608 (9)	0.40943 (8)	0.89798 (9)	0.0132 (2)
C1	0.20188 (11)	0.52274 (10)	0.44060 (11)	0.0157 (3)
C2	0.24724 (11)	0.53657 (10)	0.55218 (11)	0.0153 (3)
H2	0.2115	0.5773	0.5879	0.018*
C3	0.34448 (11)	0.49011 (10)	0.60906 (11)	0.0135 (3)
C4	0.39716 (11)	0.43306 (10)	0.55111 (11)	0.0131 (3)
C5	0.49874 (11)	0.38293 (10)	0.60028 (11)	0.0156 (3)
H5	0.5336	0.3848	0.6763	0.019*
C6	0.54664 (12)	0.33218 (11)	0.53960 (12)	0.0184 (3)
H6	0.6149	0.2997	0.5737	0.022*
C7	0.49589 (12)	0.32732 (10)	0.42648 (12)	0.0178 (3)
H7	0.5305	0.2920	0.3852	0.021*
C8	0.39727 (11)	0.37307 (10)	0.37610 (11)	0.0148 (3)
C9	0.34484 (11)	0.42711 (10)	0.43713 (11)	0.0132 (3)
C10	0.08955 (13)	0.56455 (12)	0.37809 (12)	0.0234 (3)
C11	0.34203 (12)	0.36577 (11)	0.25637 (12)	0.0188 (3)
C12	0.38962 (11)	0.49779 (10)	0.73029 (11)	0.0136 (3)
H12	0.4728	0.5004	0.7553	0.016*
C13	0.35295 (11)	0.40908 (10)	0.77995 (11)	0.0130 (3)
H13	0.3785	0.3507	0.7515	0.016*
C14	0.33521 (11)	0.43906 (11)	0.95997 (11)	0.0162 (3)
H14A	0.3039	0.5032	0.9361	0.019*
H14B	0.3805	0.4427	1.0374	0.019*
C15	0.24059 (12)	0.36724 (12)	0.94326 (12)	0.0207 (3)
H15A	0.1786	0.3981	0.9598	0.025*
H15B	0.2674	0.3127	0.9931	0.025*
C16	0.19855 (12)	0.33083 (11)	0.82632 (12)	0.0200 (3)
H16A	0.2337	0.2685	0.8226	0.024*
H16B	0.1169	0.3212	0.8024	0.024*
C17	0.22634 (11)	0.40230 (10)	0.75142 (12)	0.0159 (3)
H17A	0.1959	0.4659	0.7589	0.019*
H17B	0.1916	0.3814	0.6757	0.019*
C18	0.49755 (11)	0.35697 (10)	0.94887 (11)	0.0132 (3)
C19	0.63991 (11)	0.25860 (11)	0.92685 (12)	0.0184 (3)
H19A	0.6503	0.2196	0.8686	0.022*
H19B	0.6203	0.2148	0.9764	0.022*
C20	0.74791 (12)	0.30819 (10)	0.98754 (12)	0.0171 (3)
C21	0.80837 (13)	0.35436 (11)	0.93193 (13)	0.0226 (3)
H21	0.7803	0.3564	0.8555	0.027*
C22	0.90963 (13)	0.39735 (12)	0.98804 (15)	0.0272 (4)
H22	0.9506	0.4285	0.9498	0.033*
C23	0.95114 (13)	0.39495 (12)	1.09955 (15)	0.0285 (4)
H23	1.0207	0.4240	1.1376	0.034*
C24	0.89110 (13)	0.35018 (11)	1.15538 (14)	0.0250 (3)
H24	0.9191	0.3489	1.2318	0.030*
C25	0.78982 (12)	0.30711 (11)	1.09960 (12)	0.0198 (3)
H25	0.7487	0.2766	1.1383	0.024*

	U11	U22	U33	U12	U13	U23
F1	0.0323 (5)	0.0394 (6)	0.0246 (5)	0.0208 (5)	−0.0003 (4)	−0.0068 (5)
F2	0.0495 (7)	0.0708 (9)	0.0172 (5)	0.0375 (6)	0.0061 (5)	0.0128 (5)
F3	0.0158 (5)	0.0440 (7)	0.0709 (9)	0.0006 (4)	−0.0062 (5)	−0.0050 (6)
F4	0.0241 (4)	0.0307 (5)	0.0174 (5)	−0.0109 (4)	0.0059 (4)	−0.0066 (4)
F5	0.0312 (5)	0.0347 (5)	0.0181 (5)	0.0039 (4)	0.0130 (4)	−0.0075 (4)
F6	0.0283 (5)	0.0250 (5)	0.0139 (4)	−0.0012 (4)	0.0079 (4)	0.0029 (4)
O1	0.0231 (5)	0.0152 (5)	0.0116 (5)	0.0010 (4)	0.0020 (4)	−0.0035 (4)
O2	0.0150 (5)	0.0235 (5)	0.0129 (5)	0.0064 (4)	0.0045 (4)	−0.0003 (4)
O3	0.0198 (5)	0.0188 (5)	0.0097 (5)	0.0005 (4)	0.0025 (4)	0.0007 (4)
N1	0.0155 (5)	0.0164 (6)	0.0118 (6)	−0.0008 (4)	0.0040 (4)	0.0003 (5)
N2	0.0146 (5)	0.0171 (6)	0.0077 (5)	0.0022 (4)	0.0038 (4)	−0.0003 (4)
C1	0.0152 (6)	0.0168 (7)	0.0136 (7)	−0.0004 (5)	0.0031 (5)	0.0007 (5)
C2	0.0162 (6)	0.0167 (7)	0.0130 (7)	0.0004 (5)	0.0049 (5)	−0.0013 (5)
C3	0.0148 (6)	0.0139 (7)	0.0117 (7)	−0.0034 (5)	0.0043 (5)	−0.0001 (5)
C4	0.0145 (6)	0.0133 (6)	0.0119 (6)	−0.0017 (5)	0.0052 (5)	0.0007 (5)
C5	0.0155 (6)	0.0172 (7)	0.0126 (7)	−0.0006 (5)	0.0030 (5)	0.0026 (5)
C6	0.0156 (6)	0.0181 (7)	0.0215 (8)	0.0023 (5)	0.0062 (6)	0.0019 (6)
C7	0.0204 (7)	0.0160 (7)	0.0204 (8)	0.0000 (6)	0.0111 (6)	−0.0014 (6)
C8	0.0172 (6)	0.0142 (6)	0.0139 (7)	−0.0040 (5)	0.0064 (5)	−0.0021 (5)
C9	0.0144 (6)	0.0127 (6)	0.0129 (7)	−0.0025 (5)	0.0052 (5)	−0.0002 (5)
C10	0.0222 (7)	0.0291 (8)	0.0149 (7)	0.0065 (6)	0.0012 (6)	−0.0028 (6)
C11	0.0207 (7)	0.0223 (8)	0.0156 (7)	−0.0029 (6)	0.0090 (6)	−0.0037 (6)
C12	0.0135 (6)	0.0155 (7)	0.0105 (7)	−0.0001 (5)	0.0027 (5)	−0.0003 (5)
C13	0.0140 (6)	0.0148 (6)	0.0093 (6)	0.0000 (5)	0.0028 (5)	−0.0010 (5)
C14	0.0183 (6)	0.0189 (7)	0.0135 (7)	0.0029 (5)	0.0082 (5)	−0.0010 (5)
C15	0.0205 (7)	0.0251 (8)	0.0199 (8)	0.0012 (6)	0.0112 (6)	0.0025 (6)
C16	0.0173 (7)	0.0222 (8)	0.0201 (8)	−0.0037 (6)	0.0059 (6)	0.0029 (6)
C17	0.0133 (6)	0.0187 (7)	0.0144 (7)	−0.0003 (5)	0.0032 (5)	0.0014 (5)
C18	0.0155 (6)	0.0131 (6)	0.0109 (7)	−0.0017 (5)	0.0044 (5)	−0.0012 (5)
C19	0.0181 (7)	0.0172 (7)	0.0179 (7)	0.0052 (6)	0.0037 (5)	−0.0020 (6)
C20	0.0164 (6)	0.0132 (7)	0.0200 (8)	0.0056 (5)	0.0040 (5)	−0.0013 (6)
C21	0.0261 (8)	0.0201 (8)	0.0214 (8)	0.0027 (6)	0.0080 (6)	−0.0016 (6)
C22	0.0260 (8)	0.0214 (8)	0.0367 (10)	−0.0043 (6)	0.0140 (7)	−0.0027 (7)
C23	0.0211 (7)	0.0214 (8)	0.0376 (10)	−0.0011 (6)	0.0031 (7)	−0.0067 (7)
C24	0.0252 (8)	0.0205 (8)	0.0217 (8)	0.0053 (6)	−0.0017 (6)	−0.0021 (6)
C25	0.0204 (7)	0.0179 (7)	0.0187 (8)	0.0051 (6)	0.0034 (6)	0.0019 (6)

F1—C10	1.3284 (19)	C8—C11	1.500 (2)
F2—C10	1.3289 (19)	C12—C13	1.5500 (19)
F3—C10	1.339 (2)	C12—H12	1.0000
F4—C11	1.3485 (17)	C13—C17	1.5335 (18)
F5—C11	1.3407 (16)	C13—H13	1.0000
F6—C11	1.3443 (18)	C14—C15	1.529 (2)
O1—C12	1.4159 (17)	C14—H14A	0.9900
O1—H1O	0.840 (9)	C14—H14B	0.9900
O2—C18	1.3570 (16)	C15—C16	1.539 (2)
O2—C19	1.4600 (16)	C15—H15A	0.9900
O3—C18	1.2218 (17)	C15—H15B	0.9900
N1—C1	1.3176 (18)	C16—C17	1.532 (2)
N1—C9	1.3615 (17)	C16—H16A	0.9900
N2—C18	1.3492 (17)	C16—H16B	0.9900
N2—C13	1.4733 (17)	C17—H17A	0.9900
N2—C14	1.4736 (16)	C17—H17B	0.9900
C1—C2	1.402 (2)	C19—C20	1.508 (2)
C1—C10	1.508 (2)	C19—H19A	0.9900
C2—C3	1.3760 (19)	C19—H19B	0.9900
C2—H2	0.9500	C20—C21	1.394 (2)
C3—C4	1.4250 (19)	C20—C25	1.392 (2)
C3—C12	1.5100 (19)	C21—C22	1.389 (2)
C4—C5	1.4223 (19)	C21—H21	0.9500
C4—C9	1.4266 (19)	C22—C23	1.386 (3)
C5—C6	1.363 (2)	C22—H22	0.9500
C5—H5	0.9500	C23—C24	1.383 (2)
C6—C7	1.413 (2)	C23—H23	0.9500
C6—H6	0.9500	C24—C25	1.389 (2)
C7—C8	1.367 (2)	C24—H24	0.9500
C7—H7	0.9500	C25—H25	0.9500
C8—C9	1.4288 (19)
C12—O1—H1O	111.6 (13)	N2—C13—H13	108.1
C18—O2—C19	115.08 (11)	C17—C13—H13	108.1
C1—N1—C9	116.48 (12)	C12—C13—H13	108.1
C18—N2—C13	122.22 (11)	N2—C14—C15	109.92 (11)
C18—N2—C14	117.92 (11)	N2—C14—H14A	109.7
C13—N2—C14	116.21 (11)	C15—C14—H14A	109.7
N1—C1—C2	125.58 (13)	N2—C14—H14B	109.7
N1—C1—C10	114.54 (12)	C15—C14—H14B	109.7
C2—C1—C10	119.77 (12)	H14A—C14—H14B	108.2
C3—C2—C1	118.75 (13)	C14—C15—C16	110.48 (11)
C3—C2—H2	120.6	C14—C15—H15A	109.6
C1—C2—H2	120.6	C16—C15—H15A	109.6
C2—C3—C4	118.39 (12)	C14—C15—H15B	109.6
C2—C3—C12	119.48 (12)	C16—C15—H15B	109.6
C4—C3—C12	122.08 (12)	H15A—C15—H15B	108.1
C3—C4—C5	123.78 (13)	C17—C16—C15	110.75 (12)
C3—C4—C9	117.62 (12)	C17—C16—H16A	109.5
C5—C4—C9	118.60 (12)	C15—C16—H16A	109.5
C6—C5—C4	120.76 (13)	C17—C16—H16B	109.5
C6—C5—H5	119.6	C15—C16—H16B	109.5
C4—C5—H5	119.6	H16A—C16—H16B	108.1
C5—C6—C7	120.77 (13)	C16—C17—C13	109.86 (11)
C5—C6—H6	119.6	C16—C17—H17A	109.7
C7—C6—H6	119.6	C13—C17—H17A	109.7
C8—C7—C6	120.40 (13)	C16—C17—H17B	109.7
C8—C7—H7	119.8	C13—C17—H17B	109.7
C6—C7—H7	119.8	H17A—C17—H17B	108.2
C7—C8—C9	120.34 (13)	O3—C18—N2	125.34 (12)
C7—C8—C11	120.33 (13)	O3—C18—O2	122.70 (12)
C9—C8—C11	119.31 (12)	N2—C18—O2	111.96 (11)
N1—C9—C4	123.10 (12)	O2—C19—C20	112.88 (12)
N1—C9—C8	117.80 (12)	O2—C19—H19A	109.0
C4—C9—C8	119.10 (12)	C20—C19—H19A	109.0
F2—C10—F1	107.32 (14)	O2—C19—H19B	109.0
F2—C10—F3	106.66 (14)	C20—C19—H19B	109.0
F1—C10—F3	106.61 (13)	H19A—C19—H19B	107.8
F2—C10—C1	112.90 (13)	C21—C20—C25	119.02 (14)
F1—C10—C1	112.91 (12)	C21—C20—C19	120.30 (14)
F3—C10—C1	110.05 (13)	C25—C20—C19	120.68 (13)
F5—C11—F6	106.16 (11)	C22—C21—C20	120.15 (15)
F5—C11—F4	106.16 (12)	C22—C21—H21	119.9
F6—C11—F4	106.48 (12)	C20—C21—H21	119.9
F5—C11—C8	111.76 (12)	C23—C22—C21	120.35 (15)
F6—C11—C8	113.08 (12)	C23—C22—H22	119.8
F4—C11—C8	112.69 (11)	C21—C22—H22	119.8
O1—C12—C3	107.77 (11)	C24—C23—C22	119.87 (15)
O1—C12—C13	111.73 (11)	C24—C23—H23	120.1
C3—C12—C13	109.35 (11)	C22—C23—H23	120.1
O1—C12—H12	109.3	C23—C24—C25	119.97 (15)
C3—C12—H12	109.3	C23—C24—H24	120.0
C13—C12—H12	109.3	C25—C24—H24	120.0
N2—C13—C17	109.02 (10)	C24—C25—C20	120.64 (14)
N2—C13—C12	110.44 (11)	C24—C25—H25	119.7
C17—C13—C12	113.07 (11)	C20—C25—H25	119.7
C9—N1—C1—C2	−0.3 (2)	C9—C8—C11—F4	−63.18 (18)
C9—N1—C1—C10	−176.49 (12)	C2—C3—C12—O1	−24.67 (16)
N1—C1—C2—C3	−2.3 (2)	C4—C3—C12—O1	157.75 (12)
C10—C1—C2—C3	173.71 (13)	C2—C3—C12—C13	96.96 (15)
C1—C2—C3—C4	2.6 (2)	C4—C3—C12—C13	−80.62 (15)
C1—C2—C3—C12	−175.10 (12)	C18—N2—C13—C17	136.12 (13)
C2—C3—C4—C5	178.88 (13)	C14—N2—C13—C17	−21.86 (16)
C12—C3—C4—C5	−3.5 (2)	C18—N2—C13—C12	−99.08 (14)
C2—C3—C4—C9	−0.51 (19)	C14—N2—C13—C12	102.94 (13)
C12—C3—C4—C9	177.10 (12)	O1—C12—C13—N2	−67.05 (13)
C3—C4—C5—C6	−177.76 (13)	C3—C12—C13—N2	173.73 (10)
C9—C4—C5—C6	1.6 (2)	O1—C12—C13—C17	55.41 (15)
C4—C5—C6—C7	−0.7 (2)	C3—C12—C13—C17	−63.81 (14)
C5—C6—C7—C8	−0.4 (2)	C18—N2—C14—C15	−94.29 (15)
C6—C7—C8—C9	0.6 (2)	C13—N2—C14—C15	64.67 (15)
C6—C7—C8—C11	−178.42 (13)	N2—C14—C15—C16	−37.26 (16)
C1—N1—C9—C4	2.5 (2)	C14—C15—C16—C17	−23.02 (16)
C1—N1—C9—C8	−177.60 (12)	C15—C16—C17—C13	65.54 (15)
C3—C4—C9—N1	−2.2 (2)	N2—C13—C17—C16	−41.29 (15)
C5—C4—C9—N1	178.41 (12)	C12—C13—C17—C16	−164.53 (12)
C3—C4—C9—C8	177.97 (12)	C13—N2—C18—O3	−165.29 (13)
C5—C4—C9—C8	−1.45 (19)	C14—N2—C18—O3	−7.7 (2)
C7—C8—C9—N1	−179.50 (13)	C13—N2—C18—O2	15.20 (18)
C11—C8—C9—N1	−0.48 (19)	C14—N2—C18—O2	172.82 (11)
C7—C8—C9—C4	0.4 (2)	C19—O2—C18—O3	7.38 (19)
C11—C8—C9—C4	179.39 (12)	C19—O2—C18—N2	−173.10 (11)
N1—C1—C10—F2	−38.11 (19)	C18—O2—C19—C20	−82.15 (15)
C2—C1—C10—F2	145.43 (15)	O2—C19—C20—C21	−75.11 (16)
N1—C1—C10—F1	−160.08 (13)	O2—C19—C20—C25	106.09 (15)
C2—C1—C10—F1	23.5 (2)	C25—C20—C21—C22	0.9 (2)
N1—C1—C10—F3	80.93 (17)	C19—C20—C21—C22	−177.93 (14)
C2—C1—C10—F3	−95.52 (16)	C20—C21—C22—C23	−0.2 (2)
C7—C8—C11—F5	−3.62 (19)	C21—C22—C23—C24	−0.5 (2)
C9—C8—C11—F5	177.36 (12)	C22—C23—C24—C25	0.5 (2)
C7—C8—C11—F6	−123.34 (14)	C23—C24—C25—C20	0.2 (2)
C9—C8—C11—F6	57.64 (16)	C21—C20—C25—C24	−0.9 (2)
C7—C8—C11—F4	115.84 (14)	C19—C20—C25—C24	177.91 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O3i	0.84 (1)	1.90 (1)	2.7294 (14)	172.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O3i	0.84 (1)	1.90 (1)	2.7294 (14)	172 (2)

Symmetry code: (i) .