4-(3,3-Dimethyl-perhydro-1,3-oxa-zolo[3,4-a]pyridin-1-yl)-2,8-bis-(tri-fluoro-meth-yl)quinoline.

An L-shaped conformation is found in the title mol-ecule, C(20)H(20)F(6)N(2)O, the C-C-C-C torsion angle linking the two fused-ring systems being -92.80 (19)°. The oxazole ring adopts an envelope conformation [the N atom lies 0.579 (2) Å out of the plane defined by the remaining atoms], and the piperidine ring has a chair conformation. Supra-molecular chains are found in the crystal structure that are sustained by C-H⋯π and π-π [3.6089 (10) Å] inter-actions.

Related literature

For information on mefloquine and its derivatives, see: Maguire et al. (2006 ▶); Croft & Herxheimer (2002 ▶); Lima et al. (2002 ▶); Biot et al. (2000 ▶); Roesner et al. (1981 ▶); Kunin & Ellis (2007 ▶). For the synthesis of 1,3-oxazolidines, see: Bergmann et al. (1953 ▶); Oh et al. (2000 ▶); Saba et al. (2007 ▶); Page et al. (2007 ▶); Kukharev et al. (2007 ▶); Delgado et al. (1987 ▶). For the biological activity of 1,3-oxazolidines, see: Moloney et al. (1998 ▶); Andes et al. (2002 ▶); Kumar et al. (2009 ▶).

Experimental

Crystal data

C20H20F6N2O

M = 418.38

Triclinic,

a = 8.4192 (3) Å

b = 9.1833 (4) Å

c = 12.4424 (4) Å

α = 87.912 (2)°

β = 86.666 (2)°

γ = 78.804 (2)°

V = 941.78 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 120 K

0.65 × 0.30 × 0.25 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.643, T max = 0.746

16907 measured reflections

4275 independent reflections

3107 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.141

S = 1.06

4275 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.36 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006562/ez2202sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006562/ez2202Isup2.hkl

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

C20H20F6N2O	Z = 2
Mr = 418.38	F(000) = 432
Triclinic, P1	Dx = 1.475 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4192 (3) Å	Cell parameters from 12184 reflections
b = 9.1833 (4) Å	θ = 2.9–27.5°
c = 12.4424 (4) Å	µ = 0.13 mm−1
α = 87.912 (2)°	T = 120 K
β = 86.666 (2)°	Block, colourless
γ = 78.804 (2)°	0.65 × 0.30 × 0.25 mm
V = 941.78 (6) Å3

Nonius KappaCCD area-detector diffractometer	4275 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	3107 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.045
Detector resolution: 9.091 pixels mm-1	θmax = 27.4°, θmin = 3.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −11→11
Tmin = 0.643, Tmax = 0.746	l = −16→16
16907 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.249P] where P = (Fo2 + 2Fc2)/3
4275 reflections	(Δ/σ)max = 0.001
264 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.36 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	0.24470 (15)	0.13631 (13)	0.70186 (12)	0.0465 (4)
F2	0.48941 (14)	0.02882 (12)	0.72734 (10)	0.0376 (3)
F3	0.31274 (17)	0.05404 (14)	0.85902 (11)	0.0489 (4)
F4	1.00086 (13)	0.26530 (14)	0.94688 (10)	0.0398 (3)
F5	0.90320 (13)	0.18513 (14)	0.80980 (9)	0.0369 (3)
F6	0.80523 (14)	0.14596 (13)	0.96979 (9)	0.0357 (3)
O1	0.04978 (14)	0.65337 (14)	0.77211 (9)	0.0225 (3)
N1	0.54732 (17)	0.26383 (16)	0.83292 (11)	0.0209 (3)
N2	0.13591 (17)	0.69425 (16)	0.59985 (11)	0.0208 (3)
C1	0.4030 (2)	0.27072 (19)	0.79573 (13)	0.0205 (4)
C2	0.2882 (2)	0.40134 (19)	0.77803 (13)	0.0208 (4)
H2	0.1866	0.3973	0.7501	0.025*
C3	0.3263 (2)	0.53470 (19)	0.80200 (13)	0.0190 (4)
C4	0.4797 (2)	0.53404 (19)	0.84578 (13)	0.0183 (4)
C5	0.5296 (2)	0.6653 (2)	0.87684 (13)	0.0221 (4)
H5	0.4579	0.7585	0.8709	0.027*
C6	0.6799 (2)	0.6584 (2)	0.91518 (14)	0.0248 (4)
H6	0.7114	0.7467	0.9360	0.030*
C7	0.7882 (2)	0.5216 (2)	0.92398 (14)	0.0258 (4)
H7	0.8934	0.5188	0.9488	0.031*
C8	0.7437 (2)	0.3925 (2)	0.89724 (13)	0.0222 (4)
C9	0.5868 (2)	0.3955 (2)	0.85806 (13)	0.0195 (4)
C10	0.3631 (2)	0.1221 (2)	0.77122 (16)	0.0273 (4)
C11	0.8617 (2)	0.2472 (2)	0.90593 (15)	0.0280 (4)
C12	0.2119 (2)	0.67903 (19)	0.77676 (14)	0.0200 (4)
H12	0.2150	0.7518	0.8341	0.024*
C13	−0.0137 (2)	0.7020 (2)	0.66828 (14)	0.0225 (4)
C14	−0.1190 (2)	0.8573 (2)	0.67829 (16)	0.0313 (5)
H14A	−0.2044	0.8555	0.7351	0.047*
H14B	−0.1685	0.8881	0.6097	0.047*
H14C	−0.0516	0.9277	0.6966	0.047*
C15	−0.1106 (2)	0.5903 (2)	0.63459 (16)	0.0301 (4)
H15A	−0.0419	0.4911	0.6343	0.045*
H15B	−0.1486	0.6169	0.5622	0.045*
H15C	−0.2040	0.5908	0.6854	0.045*
C16	0.2497 (2)	0.7487 (2)	0.66532 (13)	0.0211 (4)
H16	0.2174	0.8591	0.6692	0.025*
C17	0.4194 (2)	0.7103 (2)	0.61295 (14)	0.0248 (4)
H17A	0.4541	0.6012	0.6094	0.030*
H17B	0.4965	0.7488	0.6563	0.030*
C18	0.4196 (2)	0.7800 (2)	0.49901 (15)	0.0290 (4)
H18A	0.4013	0.8895	0.5037	0.035*
H18B	0.5269	0.7463	0.4617	0.035*
C19	0.2881 (2)	0.7372 (2)	0.43406 (15)	0.0289 (4)
H19A	0.2825	0.7929	0.3643	0.035*
H19B	0.3165	0.6299	0.4189	0.035*
C20	0.1239 (2)	0.7705 (2)	0.49433 (14)	0.0251 (4)
H20A	0.0896	0.8789	0.5035	0.030*
H20B	0.0420	0.7359	0.4529	0.030*

	U11	U22	U33	U12	U13	U23
F1	0.0385 (7)	0.0273 (7)	0.0775 (10)	−0.0082 (5)	−0.0226 (7)	−0.0122 (6)
F2	0.0292 (6)	0.0254 (6)	0.0579 (8)	−0.0043 (5)	0.0073 (5)	−0.0162 (6)
F3	0.0677 (9)	0.0281 (7)	0.0531 (8)	−0.0219 (6)	0.0212 (7)	−0.0005 (6)
F4	0.0252 (6)	0.0483 (8)	0.0446 (7)	0.0006 (5)	−0.0134 (5)	−0.0066 (6)
F5	0.0292 (6)	0.0482 (8)	0.0290 (6)	0.0045 (5)	0.0007 (5)	−0.0115 (5)
F6	0.0369 (7)	0.0323 (7)	0.0348 (6)	−0.0004 (5)	−0.0030 (5)	0.0063 (5)
O1	0.0172 (6)	0.0279 (7)	0.0225 (6)	−0.0056 (5)	0.0007 (5)	0.0008 (5)
N1	0.0202 (7)	0.0227 (8)	0.0199 (7)	−0.0050 (6)	0.0032 (6)	−0.0019 (6)
N2	0.0192 (7)	0.0215 (8)	0.0218 (7)	−0.0043 (6)	−0.0002 (6)	−0.0016 (6)
C1	0.0232 (9)	0.0188 (9)	0.0199 (8)	−0.0063 (7)	0.0041 (7)	−0.0024 (7)
C2	0.0189 (8)	0.0233 (9)	0.0213 (9)	−0.0065 (7)	0.0010 (7)	−0.0026 (7)
C3	0.0192 (8)	0.0228 (9)	0.0158 (8)	−0.0065 (7)	0.0025 (6)	−0.0026 (7)
C4	0.0200 (8)	0.0214 (9)	0.0142 (8)	−0.0068 (7)	0.0026 (6)	−0.0007 (7)
C5	0.0256 (9)	0.0227 (9)	0.0192 (8)	−0.0084 (7)	0.0014 (7)	0.0001 (7)
C6	0.0287 (10)	0.0292 (10)	0.0199 (9)	−0.0138 (8)	−0.0012 (7)	−0.0020 (7)
C7	0.0212 (9)	0.0377 (11)	0.0208 (9)	−0.0109 (8)	−0.0023 (7)	−0.0008 (8)
C8	0.0189 (8)	0.0319 (10)	0.0154 (8)	−0.0048 (7)	0.0011 (6)	0.0002 (7)
C9	0.0211 (8)	0.0247 (9)	0.0138 (8)	−0.0080 (7)	0.0023 (6)	0.0004 (7)
C10	0.0231 (9)	0.0216 (9)	0.0373 (11)	−0.0057 (7)	0.0032 (8)	−0.0038 (8)
C11	0.0220 (9)	0.0368 (11)	0.0244 (10)	−0.0030 (8)	−0.0026 (7)	−0.0046 (8)
C12	0.0186 (8)	0.0210 (9)	0.0213 (9)	−0.0056 (7)	−0.0002 (6)	−0.0032 (7)
C13	0.0208 (9)	0.0229 (9)	0.0230 (9)	−0.0021 (7)	−0.0011 (7)	−0.0013 (7)
C14	0.0270 (10)	0.0282 (11)	0.0354 (11)	0.0014 (8)	0.0035 (8)	0.0004 (8)
C15	0.0240 (10)	0.0369 (11)	0.0315 (10)	−0.0111 (8)	−0.0004 (8)	−0.0041 (9)
C16	0.0230 (9)	0.0202 (9)	0.0214 (9)	−0.0075 (7)	−0.0008 (7)	−0.0018 (7)
C17	0.0216 (9)	0.0297 (10)	0.0242 (9)	−0.0085 (8)	0.0005 (7)	0.0006 (8)
C18	0.0262 (10)	0.0349 (11)	0.0264 (10)	−0.0093 (8)	0.0039 (7)	0.0030 (8)
C19	0.0301 (10)	0.0345 (11)	0.0223 (9)	−0.0077 (8)	0.0025 (7)	−0.0009 (8)
C20	0.0257 (9)	0.0267 (10)	0.0227 (9)	−0.0041 (8)	−0.0025 (7)	−0.0005 (7)

F1—C10	1.341 (2)	C7—H7	0.9500
F2—C10	1.333 (2)	C8—C9	1.429 (2)
F3—C10	1.328 (2)	C8—C11	1.506 (3)
F4—C11	1.346 (2)	C12—C16	1.548 (2)
F5—C11	1.342 (2)	C12—H12	1.0000
F6—C11	1.340 (2)	C13—C15	1.513 (3)
O1—C12	1.434 (2)	C13—C14	1.531 (3)
O1—C13	1.449 (2)	C14—H14A	0.9800
N1—C1	1.315 (2)	C14—H14B	0.9800
N1—C9	1.366 (2)	C14—H14C	0.9800
N2—C16	1.462 (2)	C15—H15A	0.9800
N2—C20	1.465 (2)	C15—H15B	0.9800
N2—C13	1.470 (2)	C15—H15C	0.9800
C1—C2	1.406 (2)	C16—C17	1.518 (2)
C1—C10	1.513 (2)	C16—H16	1.0000
C2—C3	1.372 (2)	C17—C18	1.534 (3)
C2—H2	0.9500	C17—H17A	0.9900
C3—C4	1.429 (2)	C17—H17B	0.9900
C3—C12	1.514 (2)	C18—C19	1.527 (3)
C4—C9	1.419 (2)	C18—H18A	0.9900
C4—C5	1.424 (2)	C18—H18B	0.9900
C5—C6	1.367 (3)	C19—C20	1.516 (3)
C5—H5	0.9500	C19—H19A	0.9900
C6—C7	1.407 (3)	C19—H19B	0.9900
C6—H6	0.9500	C20—H20A	0.9900
C7—C8	1.368 (3)	C20—H20B	0.9900
C12—O1—C13	110.26 (13)	C16—C12—H12	109.4
C1—N1—C9	116.60 (15)	O1—C13—N2	101.73 (13)
C16—N2—C20	111.29 (14)	O1—C13—C15	107.83 (15)
C16—N2—C13	105.69 (13)	N2—C13—C15	110.94 (14)
C20—N2—C13	117.78 (14)	O1—C13—C14	109.00 (14)
N1—C1—C2	125.68 (16)	N2—C13—C14	115.09 (15)
N1—C1—C10	114.78 (16)	C15—C13—C14	111.56 (15)
C2—C1—C10	119.54 (15)	C13—C14—H14A	109.5
C3—C2—C1	118.53 (16)	C13—C14—H14B	109.5
C3—C2—H2	120.7	H14A—C14—H14B	109.5
C1—C2—H2	120.7	C13—C14—H14C	109.5
C2—C3—C4	118.39 (16)	H14A—C14—H14C	109.5
C2—C3—C12	120.45 (15)	H14B—C14—H14C	109.5
C4—C3—C12	121.08 (15)	C13—C15—H15A	109.5
C9—C4—C5	118.85 (15)	C13—C15—H15B	109.5
C9—C4—C3	117.96 (15)	H15A—C15—H15B	109.5
C5—C4—C3	123.19 (16)	C13—C15—H15C	109.5
C6—C5—C4	120.61 (17)	H15A—C15—H15C	109.5
C6—C5—H5	119.7	H15B—C15—H15C	109.5
C4—C5—H5	119.7	N2—C16—C17	109.60 (14)
C5—C6—C7	120.52 (17)	N2—C16—C12	100.79 (13)
C5—C6—H6	119.7	C17—C16—C12	119.71 (15)
C7—C6—H6	119.7	N2—C16—H16	108.7
C8—C7—C6	120.74 (16)	C17—C16—H16	108.7
C8—C7—H7	119.6	C12—C16—H16	108.7
C6—C7—H7	119.6	C16—C17—C18	109.14 (15)
C7—C8—C9	120.17 (17)	C16—C17—H17A	109.9
C7—C8—C11	120.07 (16)	C18—C17—H17A	109.9
C9—C8—C11	119.74 (16)	C16—C17—H17B	109.9
N1—C9—C4	122.79 (15)	C18—C17—H17B	109.9
N1—C9—C8	118.15 (16)	H17A—C17—H17B	108.3
C4—C9—C8	119.06 (16)	C19—C18—C17	111.21 (15)
F3—C10—F2	106.77 (16)	C19—C18—H18A	109.4
F3—C10—F1	106.58 (16)	C17—C18—H18A	109.4
F2—C10—F1	106.43 (15)	C19—C18—H18B	109.4
F3—C10—C1	112.06 (16)	C17—C18—H18B	109.4
F2—C10—C1	112.82 (15)	H18A—C18—H18B	108.0
F1—C10—C1	111.76 (16)	C20—C19—C18	111.32 (15)
F6—C11—F5	106.96 (16)	C20—C19—H19A	109.4
F6—C11—F4	106.30 (15)	C18—C19—H19A	109.4
F5—C11—F4	106.15 (14)	C20—C19—H19B	109.4
F6—C11—C8	113.30 (14)	C18—C19—H19B	109.4
F5—C11—C8	112.29 (15)	H19A—C19—H19B	108.0
F4—C11—C8	111.37 (16)	N2—C20—C19	108.88 (15)
O1—C12—C3	109.96 (14)	N2—C20—H20A	109.9
O1—C12—C16	104.86 (13)	C19—C20—H20A	109.9
C3—C12—C16	113.55 (14)	N2—C20—H20B	109.9
O1—C12—H12	109.4	C19—C20—H20B	109.9
C3—C12—H12	109.4	H20A—C20—H20B	108.3
C9—N1—C1—C2	1.2 (3)	C7—C8—C11—F5	−115.48 (18)
C9—N1—C1—C10	−178.76 (14)	C9—C8—C11—F5	62.7 (2)
N1—C1—C2—C3	−0.7 (3)	C7—C8—C11—F4	3.4 (2)
C10—C1—C2—C3	179.25 (16)	C9—C8—C11—F4	−178.36 (15)
C1—C2—C3—C4	−1.2 (2)	C13—O1—C12—C3	−122.74 (14)
C1—C2—C3—C12	175.52 (14)	C13—O1—C12—C16	−0.32 (17)
C2—C3—C4—C9	2.4 (2)	C2—C3—C12—O1	24.3 (2)
C12—C3—C4—C9	−174.25 (14)	C4—C3—C12—O1	−159.06 (14)
C2—C3—C4—C5	−177.91 (15)	C2—C3—C12—C16	−92.80 (19)
C12—C3—C4—C5	5.4 (2)	C4—C3—C12—C16	83.81 (18)
C9—C4—C5—C6	1.7 (2)	C12—O1—C13—N2	23.98 (16)
C3—C4—C5—C6	−177.97 (16)	C12—O1—C13—C15	140.73 (14)
C4—C5—C6—C7	0.4 (3)	C12—O1—C13—C14	−98.00 (16)
C5—C6—C7—C8	−1.8 (3)	C16—N2—C13—O1	−39.80 (16)
C6—C7—C8—C9	1.1 (3)	C20—N2—C13—O1	−164.85 (14)
C6—C7—C8—C11	179.30 (16)	C16—N2—C13—C15	−154.28 (15)
C1—N1—C9—C4	0.2 (2)	C20—N2—C13—C15	80.67 (19)
C1—N1—C9—C8	−179.11 (15)	C16—N2—C13—C14	77.87 (18)
C5—C4—C9—N1	178.31 (15)	C20—N2—C13—C14	−47.2 (2)
C3—C4—C9—N1	−2.0 (2)	C20—N2—C16—C17	−64.79 (18)
C5—C4—C9—C8	−2.4 (2)	C13—N2—C16—C17	166.23 (14)
C3—C4—C9—C8	177.30 (14)	C20—N2—C16—C12	168.10 (13)
C7—C8—C9—N1	−179.65 (15)	C13—N2—C16—C12	39.12 (16)
C11—C8—C9—N1	2.1 (2)	O1—C12—C16—N2	−23.53 (16)
C7—C8—C9—C4	1.0 (2)	C3—C12—C16—N2	96.54 (15)
C11—C8—C9—C4	−177.20 (14)	O1—C12—C16—C17	−143.66 (15)
N1—C1—C10—F3	81.59 (19)	C3—C12—C16—C17	−23.6 (2)
C2—C1—C10—F3	−98.4 (2)	N2—C16—C17—C18	58.38 (19)
N1—C1—C10—F2	−39.0 (2)	C12—C16—C17—C18	173.97 (15)
C2—C1—C10—F2	141.05 (17)	C16—C17—C18—C19	−52.9 (2)
N1—C1—C10—F1	−158.85 (15)	C17—C18—C19—C20	52.4 (2)
C2—C1—C10—F1	21.2 (2)	C16—N2—C20—C19	62.59 (18)
C7—C8—C11—F6	123.21 (18)	C13—N2—C20—C19	−175.18 (15)
C9—C8—C11—F6	−58.6 (2)	C18—C19—C20—N2	−55.9 (2)

Cg is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15c···Cgi	0.98	2.87	3.781 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15c⋯Cgi	0.98	2.87	3.781 (2)	155

Symmetry code: (i) .