2-{1-[2,8-Bis(trifluoro-meth-yl)quinolin-4-yl]-3,5,6,7,8,8a-hexa-hydro-1H-1,3-oxazolo[3,4-a]pyridin-3-yl}phenol.

In the title mefloquine-oxazolidine derivative, C(24)H(20)F(6)N(2)O(2), the oxazoline ring adopts an envelope conformation (the flap atom is N) and the piperidine ring has a chair conformation. The oxazoline and benzene residues lie away from the C(6) ring of the quinoline group and, to a first approximation, to one side of the plane through the ten atoms (r.m.s. deviation = 0.025 Å). An intra-molecular O-H⋯N(piperidine) hydrogen bond is present. The crystal packing features C-H⋯O, C-H⋯F and C-H⋯π(hy-droxy-benzene) inter-actions.

Related literature

For background to the anti-mycobacterial activities of quinoline derivatives related to mefloquine, see: Gonçalves et al. (2010 ▶). For additional geometric analysis, see: Cremer & Pople (1975 ▶); Spek (2009 ▶).

Experimental

Crystal data

C24H20F6N2O2

M = 482.42

Orthorhombic,

a = 27.2766 (11) Å

b = 34.1005 (9) Å

c = 9.4431 (2) Å

V = 8783.5 (5) Å3

Z = 16

Mo Kα radiation

μ = 0.13 mm−1

T = 120 K

0.40 × 0.20 × 0.16 mm

Data collection

Enraf–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.799, T max = 1.000

13970 measured reflections

2660 independent reflections

2519 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.082

S = 1.10

2660 reflections

308 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; 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: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022379/hb5905sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022379/hb5905Isup2.hkl

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

C24H20F6N2O2	F(000) = 3968
Mr = 482.42	Dx = 1.459 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 11047 reflections
a = 27.2766 (11) Å	θ = 2.9–27.5°
b = 34.1005 (9) Å	µ = 0.13 mm−1
c = 9.4431 (2) Å	T = 120 K
V = 8783.5 (5) Å3	Block, colourless
Z = 16	0.40 × 0.20 × 0.16 mm

Enraf–Nonius KappaCCD diffractometer	2660 independent reflections
Radiation source: Enraf–Nonius FR591 rotating anode	2519 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.043
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −35→32
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −44→32
Tmin = 0.799, Tmax = 1.000	l = −11→12
13970 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0295P)2 + 15.365P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2660 reflections	Δρmax = 0.20 e Å−3
308 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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	0.98349 (6)	0.85851 (4)	0.25475 (17)	0.0325 (3)
F2	1.03760 (5)	0.81329 (5)	0.22731 (16)	0.0352 (4)
F3	0.96194 (6)	0.80141 (5)	0.18235 (15)	0.0332 (4)
F4	0.83400 (6)	0.81192 (5)	0.47423 (18)	0.0387 (4)
F5	0.85056 (6)	0.75173 (5)	0.4262 (2)	0.0435 (4)
F6	0.79918 (6)	0.76574 (6)	0.59082 (19)	0.0433 (4)
O1	1.10450 (6)	0.78733 (5)	0.67372 (18)	0.0214 (3)
O2	1.10905 (7)	0.87646 (6)	0.4756 (2)	0.0331 (4)
H2O	1.0968	0.8720	0.5556	0.050*
N1	0.93890 (7)	0.79834 (6)	0.4583 (2)	0.0203 (4)
N2	1.10727 (7)	0.85110 (6)	0.7433 (2)	0.0226 (4)
C1	0.98410 (8)	0.80770 (6)	0.4242 (2)	0.0187 (4)
C2	1.02460 (8)	0.80730 (6)	0.5156 (2)	0.0198 (4)
H2	1.0563	0.8139	0.4816	0.024*
C3	1.01759 (8)	0.79725 (6)	0.6548 (2)	0.0176 (4)
C4	0.96894 (8)	0.78816 (6)	0.7003 (2)	0.0189 (4)
C5	0.95739 (9)	0.77823 (7)	0.8426 (3)	0.0214 (5)
H5	0.9824	0.7786	0.9125	0.026*
C6	0.91067 (9)	0.76812 (7)	0.8798 (3)	0.0233 (5)
H6	0.9034	0.7616	0.9753	0.028*
C7	0.87321 (9)	0.76741 (7)	0.7767 (3)	0.0242 (5)
H7	0.8409	0.7600	0.8033	0.029*
C8	0.88277 (8)	0.77726 (7)	0.6394 (3)	0.0212 (5)
C9	0.93106 (8)	0.78838 (6)	0.5973 (2)	0.0186 (4)
C10	0.99188 (8)	0.82002 (7)	0.2718 (3)	0.0236 (5)
C11	0.84193 (9)	0.77694 (8)	0.5328 (3)	0.0273 (5)
C12	1.06091 (8)	0.79426 (7)	0.7548 (2)	0.0201 (4)
H12	1.0556	0.7719	0.8218	0.024*
C13	1.13849 (8)	0.81902 (7)	0.6950 (3)	0.0231 (5)
H13	1.1626	0.8119	0.7707	0.028*
C14	1.07232 (8)	0.83156 (7)	0.8391 (3)	0.0224 (5)
H14	1.0902	0.8239	0.9273	0.027*
C15	1.03185 (9)	0.85983 (7)	0.8790 (3)	0.0257 (5)
H15A	1.0080	0.8467	0.9422	0.031*
H15B	1.0143	0.8687	0.7930	0.031*
C16	1.05498 (10)	0.89492 (8)	0.9549 (3)	0.0313 (6)
H16A	1.0294	0.9147	0.9750	0.038*
H16B	1.0690	0.8862	1.0463	0.038*
C17	1.09526 (10)	0.91343 (8)	0.8645 (3)	0.0341 (6)
H17A	1.0803	0.9258	0.7801	0.041*
H17B	1.1119	0.9342	0.9198	0.041*
C18	1.13303 (9)	0.88317 (8)	0.8172 (3)	0.0310 (6)
H18A	1.1572	0.8955	0.7528	0.037*
H18B	1.1508	0.8727	0.9004	0.037*
C19	1.16494 (9)	0.82626 (7)	0.5575 (3)	0.0262 (5)
C20	1.14874 (9)	0.85282 (7)	0.4556 (3)	0.0287 (5)
C21	1.17304 (11)	0.85539 (8)	0.3246 (3)	0.0372 (7)
H21	1.1618	0.8734	0.2550	0.045*
C22	1.21281 (12)	0.83207 (9)	0.2970 (4)	0.0431 (7)
H22	1.2291	0.8341	0.2083	0.052*
C23	1.22951 (11)	0.80566 (9)	0.3970 (4)	0.0417 (7)
H23	1.2570	0.7895	0.3770	0.050*
C24	1.20596 (10)	0.80299 (8)	0.5263 (3)	0.0331 (6)
H24	1.2178	0.7851	0.5953	0.040*

	U11	U22	U33	U12	U13	U23
F1	0.0439 (9)	0.0275 (8)	0.0262 (8)	0.0023 (6)	−0.0006 (7)	0.0088 (6)
F2	0.0274 (7)	0.0554 (10)	0.0227 (8)	0.0085 (7)	0.0077 (6)	0.0121 (7)
F3	0.0377 (9)	0.0460 (9)	0.0160 (7)	−0.0085 (7)	−0.0028 (6)	−0.0014 (7)
F4	0.0344 (8)	0.0471 (9)	0.0347 (9)	0.0040 (7)	−0.0083 (7)	0.0118 (8)
F5	0.0339 (8)	0.0578 (11)	0.0387 (9)	−0.0042 (8)	−0.0057 (8)	−0.0217 (9)
F6	0.0202 (7)	0.0723 (12)	0.0373 (10)	−0.0094 (7)	0.0010 (7)	0.0083 (9)
O1	0.0193 (8)	0.0214 (7)	0.0236 (8)	−0.0016 (6)	−0.0005 (7)	−0.0004 (7)
O2	0.0363 (10)	0.0313 (9)	0.0316 (10)	0.0013 (8)	0.0036 (8)	0.0049 (8)
N1	0.0217 (9)	0.0222 (9)	0.0170 (10)	−0.0002 (7)	0.0003 (8)	−0.0004 (7)
N2	0.0221 (9)	0.0236 (9)	0.0222 (10)	−0.0038 (7)	−0.0015 (8)	−0.0026 (8)
C1	0.0217 (11)	0.0182 (10)	0.0162 (10)	0.0003 (8)	0.0000 (9)	0.0001 (8)
C2	0.0211 (10)	0.0186 (10)	0.0196 (11)	−0.0006 (8)	0.0007 (9)	0.0009 (9)
C3	0.0197 (10)	0.0155 (9)	0.0175 (11)	−0.0002 (8)	−0.0019 (8)	−0.0010 (8)
C4	0.0218 (10)	0.0166 (9)	0.0184 (11)	0.0000 (8)	0.0015 (9)	0.0014 (9)
C5	0.0266 (12)	0.0213 (11)	0.0164 (11)	0.0000 (9)	0.0002 (9)	0.0009 (9)
C6	0.0270 (12)	0.0240 (11)	0.0188 (11)	0.0036 (9)	0.0044 (9)	0.0026 (9)
C7	0.0213 (11)	0.0238 (11)	0.0275 (12)	0.0017 (9)	0.0054 (10)	0.0017 (10)
C8	0.0205 (11)	0.0217 (11)	0.0215 (11)	−0.0003 (9)	0.0005 (9)	−0.0002 (9)
C9	0.0205 (10)	0.0173 (10)	0.0180 (11)	−0.0002 (8)	0.0013 (9)	−0.0008 (8)
C10	0.0233 (11)	0.0278 (12)	0.0197 (11)	−0.0008 (9)	−0.0010 (10)	0.0005 (10)
C11	0.0210 (11)	0.0351 (13)	0.0257 (12)	−0.0012 (10)	0.0014 (10)	−0.0002 (10)
C12	0.0205 (10)	0.0209 (10)	0.0189 (11)	−0.0018 (8)	−0.0006 (9)	0.0014 (9)
C13	0.0192 (10)	0.0248 (11)	0.0252 (13)	−0.0023 (8)	−0.0043 (9)	0.0010 (9)
C14	0.0223 (11)	0.0273 (11)	0.0175 (11)	−0.0033 (9)	−0.0035 (9)	−0.0019 (9)
C15	0.0280 (12)	0.0258 (12)	0.0232 (12)	−0.0033 (9)	0.0013 (10)	−0.0053 (10)
C16	0.0319 (13)	0.0308 (13)	0.0311 (14)	−0.0035 (10)	0.0018 (11)	−0.0109 (11)
C17	0.0362 (14)	0.0282 (13)	0.0379 (15)	−0.0092 (10)	0.0037 (12)	−0.0117 (11)
C18	0.0281 (12)	0.0311 (13)	0.0338 (14)	−0.0078 (10)	−0.0015 (11)	−0.0068 (11)
C19	0.0237 (12)	0.0261 (12)	0.0287 (13)	−0.0051 (9)	0.0027 (10)	−0.0030 (10)
C20	0.0310 (13)	0.0243 (11)	0.0307 (14)	−0.0067 (9)	0.0035 (11)	−0.0017 (10)
C21	0.0514 (17)	0.0286 (13)	0.0316 (15)	−0.0107 (12)	0.0096 (13)	0.0003 (12)
C22	0.0508 (17)	0.0393 (16)	0.0391 (17)	−0.0136 (13)	0.0220 (14)	−0.0087 (13)
C23	0.0344 (15)	0.0373 (15)	0.0535 (19)	−0.0066 (13)	0.0163 (14)	−0.0119 (14)
C24	0.0265 (12)	0.0285 (13)	0.0444 (16)	−0.0030 (10)	0.0034 (12)	−0.0038 (12)

F1—C10	1.342 (3)	C8—C9	1.427 (3)
F2—C10	1.336 (3)	C8—C11	1.502 (3)
F3—C10	1.336 (3)	C12—C14	1.532 (3)
F4—C11	1.332 (3)	C12—H12	1.0000
F5—C11	1.344 (3)	C13—C19	1.506 (3)
F6—C11	1.344 (3)	C13—H13	1.0000
O1—C12	1.434 (3)	C14—C15	1.514 (3)
O1—C13	1.438 (3)	C14—H14	1.0000
O2—C20	1.363 (3)	C15—C16	1.530 (3)
O2—H2O	0.8400	C15—H15A	0.9900
N1—C1	1.314 (3)	C15—H15B	0.9900
N1—C9	1.372 (3)	C16—C17	1.528 (4)
N2—C13	1.460 (3)	C16—H16A	0.9900
N2—C14	1.473 (3)	C16—H16B	0.9900
N2—C18	1.475 (3)	C17—C18	1.525 (4)
C1—C2	1.401 (3)	C17—H17A	0.9900
C1—C10	1.514 (3)	C17—H17B	0.9900
C2—C3	1.372 (3)	C18—H18A	0.9900
C2—H2	0.9500	C18—H18B	0.9900
C3—C4	1.429 (3)	C19—C20	1.393 (4)
C3—C12	1.516 (3)	C19—C24	1.403 (4)
C4—C9	1.419 (3)	C20—C21	1.406 (4)
C4—C5	1.421 (3)	C21—C22	1.370 (4)
C5—C6	1.366 (3)	C21—H21	0.9500
C5—H5	0.9500	C22—C23	1.382 (5)
C6—C7	1.411 (3)	C22—H22	0.9500
C6—H6	0.9500	C23—C24	1.382 (4)
C7—C8	1.364 (3)	C23—H23	0.9500
C7—H7	0.9500	C24—H24	0.9500
C12—O1—C13	109.65 (17)	N2—C13—C19	115.2 (2)
C20—O2—H2O	109.5	O1—C13—H13	110.0
C1—N1—C9	116.2 (2)	N2—C13—H13	110.0
C13—N2—C14	103.32 (18)	C19—C13—H13	110.0
C13—N2—C18	115.18 (19)	N2—C14—C15	109.69 (19)
C14—N2—C18	110.72 (19)	N2—C14—C12	100.86 (18)
N1—C1—C2	125.9 (2)	C15—C14—C12	120.68 (19)
N1—C1—C10	115.6 (2)	N2—C14—H14	108.3
C2—C1—C10	118.5 (2)	C15—C14—H14	108.3
C3—C2—C1	118.8 (2)	C12—C14—H14	108.3
C3—C2—H2	120.6	C14—C15—C16	108.3 (2)
C1—C2—H2	120.6	C14—C15—H15A	110.0
C2—C3—C4	118.1 (2)	C16—C15—H15A	110.0
C2—C3—C12	120.3 (2)	C14—C15—H15B	110.0
C4—C3—C12	121.48 (19)	C16—C15—H15B	110.0
C9—C4—C5	119.2 (2)	H15A—C15—H15B	108.4
C9—C4—C3	118.0 (2)	C17—C16—C15	111.0 (2)
C5—C4—C3	122.8 (2)	C17—C16—H16A	109.4
C6—C5—C4	120.7 (2)	C15—C16—H16A	109.4
C6—C5—H5	119.7	C17—C16—H16B	109.4
C4—C5—H5	119.7	C15—C16—H16B	109.4
C5—C6—C7	120.1 (2)	H16A—C16—H16B	108.0
C5—C6—H6	119.9	C18—C17—C16	111.7 (2)
C7—C6—H6	119.9	C18—C17—H17A	109.3
C8—C7—C6	120.8 (2)	C16—C17—H17A	109.3
C8—C7—H7	119.6	C18—C17—H17B	109.3
C6—C7—H7	119.6	C16—C17—H17B	109.3
C7—C8—C9	120.4 (2)	H17A—C17—H17B	107.9
C7—C8—C11	119.6 (2)	N2—C18—C17	108.6 (2)
C9—C8—C11	120.0 (2)	N2—C18—H18A	110.0
N1—C9—C4	122.9 (2)	C17—C18—H18A	110.0
N1—C9—C8	118.4 (2)	N2—C18—H18B	110.0
C4—C9—C8	118.7 (2)	C17—C18—H18B	110.0
F3—C10—F2	106.9 (2)	H18A—C18—H18B	108.4
F3—C10—F1	106.50 (19)	C20—C19—C24	118.4 (2)
F2—C10—F1	106.81 (19)	C20—C19—C13	123.4 (2)
F3—C10—C1	112.58 (19)	C24—C19—C13	118.1 (2)
F2—C10—C1	112.49 (19)	O2—C20—C19	122.7 (2)
F1—C10—C1	111.2 (2)	O2—C20—C21	117.4 (2)
F4—C11—F6	106.4 (2)	C19—C20—C21	119.9 (2)
F4—C11—F5	106.9 (2)	C22—C21—C20	120.3 (3)
F6—C11—F5	106.0 (2)	C22—C21—H21	119.9
F4—C11—C8	113.1 (2)	C20—C21—H21	119.9
F6—C11—C8	111.8 (2)	C21—C22—C23	120.6 (3)
F5—C11—C8	112.1 (2)	C21—C22—H22	119.7
O1—C12—C3	108.97 (18)	C23—C22—H22	119.7
O1—C12—C14	104.21 (17)	C22—C23—C24	119.5 (3)
C3—C12—C14	115.21 (19)	C22—C23—H23	120.2
O1—C12—H12	109.4	C24—C23—H23	120.2
C3—C12—H12	109.4	C23—C24—C19	121.2 (3)
C14—C12—H12	109.4	C23—C24—H24	119.4
O1—C13—N2	103.34 (18)	C19—C24—H24	119.4
O1—C13—C19	108.15 (19)
C9—N1—C1—C2	1.9 (3)	C2—C3—C12—O1	−23.2 (3)
C9—N1—C1—C10	−177.92 (19)	C4—C3—C12—O1	154.04 (19)
N1—C1—C2—C3	−1.7 (3)	C2—C3—C12—C14	93.5 (3)
C10—C1—C2—C3	178.2 (2)	C4—C3—C12—C14	−89.3 (3)
C1—C2—C3—C4	−0.8 (3)	C12—O1—C13—N2	−21.6 (2)
C1—C2—C3—C12	176.54 (19)	C12—O1—C13—C19	−144.21 (19)
C2—C3—C4—C9	2.7 (3)	C14—N2—C13—O1	40.1 (2)
C12—C3—C4—C9	−174.6 (2)	C18—N2—C13—O1	160.9 (2)
C2—C3—C4—C5	−178.6 (2)	C14—N2—C13—C19	157.82 (19)
C12—C3—C4—C5	4.1 (3)	C18—N2—C13—C19	−81.3 (3)
C9—C4—C5—C6	1.5 (3)	C13—N2—C14—C15	−170.42 (19)
C3—C4—C5—C6	−177.2 (2)	C18—N2—C14—C15	65.7 (2)
C4—C5—C6—C7	0.0 (4)	C13—N2—C14—C12	−42.1 (2)
C5—C6—C7—C8	−0.9 (4)	C18—N2—C14—C12	−165.92 (19)
C6—C7—C8—C9	0.2 (4)	O1—C12—C14—N2	28.6 (2)
C6—C7—C8—C11	−178.9 (2)	C3—C12—C14—N2	−90.8 (2)
C1—N1—C9—C4	0.3 (3)	O1—C12—C14—C15	149.4 (2)
C1—N1—C9—C8	−178.9 (2)	C3—C12—C14—C15	30.1 (3)
C5—C4—C9—N1	178.7 (2)	N2—C14—C15—C16	−60.6 (3)
C3—C4—C9—N1	−2.6 (3)	C12—C14—C15—C16	−177.0 (2)
C5—C4—C9—C8	−2.1 (3)	C14—C15—C16—C17	54.6 (3)
C3—C4—C9—C8	176.6 (2)	C15—C16—C17—C18	−53.1 (3)
C7—C8—C9—N1	−179.5 (2)	C13—N2—C18—C17	−178.2 (2)
C11—C8—C9—N1	−0.4 (3)	C14—N2—C18—C17	−61.5 (3)
C7—C8—C9—C4	1.3 (3)	C16—C17—C18—N2	55.2 (3)
C11—C8—C9—C4	−179.6 (2)	O1—C13—C19—C20	91.1 (3)
N1—C1—C10—F3	−32.8 (3)	N2—C13—C19—C20	−23.9 (3)
C2—C1—C10—F3	147.4 (2)	O1—C13—C19—C24	−84.1 (3)
N1—C1—C10—F2	−153.6 (2)	N2—C13—C19—C24	160.9 (2)
C2—C1—C10—F2	26.6 (3)	C24—C19—C20—O2	179.5 (2)
N1—C1—C10—F1	86.7 (2)	C13—C19—C20—O2	4.3 (4)
C2—C1—C10—F1	−93.2 (2)	C24—C19—C20—C21	0.8 (4)
C7—C8—C11—F4	119.2 (3)	C13—C19—C20—C21	−174.4 (2)
C9—C8—C11—F4	−59.9 (3)	O2—C20—C21—C22	−179.1 (3)
C7—C8—C11—F6	−0.9 (3)	C19—C20—C21—C22	−0.4 (4)
C9—C8—C11—F6	179.9 (2)	C20—C21—C22—C23	0.2 (5)
C7—C8—C11—F5	−119.8 (3)	C21—C22—C23—C24	−0.4 (5)
C9—C8—C11—F5	61.0 (3)	C22—C23—C24—C19	0.8 (4)
C13—O1—C12—C3	118.85 (19)	C20—C19—C24—C23	−1.0 (4)
C13—O1—C12—C14	−4.6 (2)	C13—C19—C24—C23	174.4 (2)

Cg1 is the centroid of the benzene ring C19–C24.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N2	0.84	1.93	2.672 (3)	146
C6—H6···O1i	0.95	2.52	3.384 (3)	152
C16—H16B···F4ii	0.99	2.47	3.043 (3)	116
C18—H18B···F1ii	0.99	2.54	3.275 (3)	131
C15—H15B···Cg1iii	0.99	2.93	3.792 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring C19–C24.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯N2	0.84	1.93	2.672 (3)	146
C6—H6⋯O1i	0.95	2.52	3.384 (3)	152
C16—H16B⋯F4ii	0.99	2.47	3.043 (3)	116
C18—H18B⋯F1ii	0.99	2.54	3.275 (3)	131
C15—H15B⋯Cg1iii	0.99	2.93	3.792 (3)	146

Symmetry codes: (i) ; (ii) ; (iii) .