4-(3,3-Dimethyl­perhydro-1,3-oxa­zolo[3,4-a]pyridin-1-yl)-2,8-bis­(tri­fluoro­meth­yl)quinoline

Wardell, J.L.; Wardell, S.M.S.V.; Tiekink, E.R.T.

doi:10.1107/S1600536810006562

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o700-o701

doi:10.1107/S1600536810006562

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4-(3,3-Dimethylperhydro-1,3-oxazolo[3,4-a]pyridin-1-yl)-2,8-bis(trifluoromethyl)quinoline

James L. Wardell,^a ‡ Solange M. S. V. Wardell ^b and Edward R. T. Tiekink ^c ^*

^aCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, ^bCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 15 February 2010; accepted 19 February 2010; online 27 February 2010)

An L-shaped conformation is found in the title molecule, C₂₀H₂₀F₆N₂O, 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. Supramolecular chains are found in the crystal structure that are sustained by C—H⋯π and π–π [3.6089 (10) Å] interactions.

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_r = 418.38
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.141
S = 1.06
4275 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) x-1, y, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Mefloquine, manufactured as the racemic erythro hydrochloride salt is a synthetic analogue of quinine used in the prevention and treatment for malaria in combination with other drugs (Maguire et al., 2006). However, despite its efficacy, this orally-administered drug possesses several important physical and psychological adverse side-effects, such as birth defects, anxiety, aggression, seizures, nightmares, neuropathy, insomnia, central nervous system problems, acute depression, urinary disorders, etc. (Croft & Herxheimer, 2002). Due to these effects, mefloquine analogues have been synthesized with the goals of increasing the efficacy and eliminating adverse side-effects (Lima et al., 2002; Biot et al., 2000; Roesner et al., 1981). Mefloquine derivatives are also undergoing tests against other diseases, for example, as anti-viral and anti-tuberculosis agents (Kunin & Ellis, 2007). In the quest for new derivatives, the title compound, 5-[2,8-bis(trifluoromethyl)quinolin-4-yl)-hexahydro-3H-oxazolo[3,4-a]pyridine-2-oxaindolizidine (I) has been obtained.

Oxazolidines are frequently prepared from 2-amino-1-hydroxyalkanes and carbonyl compounds (Bergmann et al., 1953; Oh et al., 2000; Saba et al., 2007; Page et al., 2007); in particular cases, azeotropic removal of water or the use of a catalyst is involved (Page et al., 2007). However, problems of stability of oxazolidines and formation of tautomeric mixtures of the oxazolidines and the corresponding imines can limit or complicate this synthetic route (Page et al., 2007). Alternative routes to hexahydro-3H-oxazolo[3,4-a]pyridine derivatives include the Hg(OAc)₂ catalysed cyclization of 2-(vinyloxymethyl)piperidine (Kukharev et al., 2007) and use of 1-naphthalenyl 2-pyridinyl ketone (Delgado et al., 1987). 1,3-Oxazolidine derivatives, in general, have been shown to have useful biological activities (Moloney et al., 1998; Andes et al., 2002; Kumar et al., 2009). The title compound, (I), was isolated unexpectedly from a solution of mefloquine hydrochloride and 2-hydroxybenzoic acid in acetone, followed by initial by recrystallisation from isopropanol, and finally from EtOH.

The molecular structure of (I), Fig. 1, adopts an L-shaped conformation with the quinoline group being approximately orthogonal to the rest of the molecule; for example, the C2–C3–C12–C16 torsion angle is -92.80 (19) °. The five-membered oxazole ring adopts an envelope conformation with the N2 atom lying 0.579 (2) Å out of the plane defined by the remaining atoms. The piperidine ring adopts a chair conformation. The presence of C–H···π, Table 1, and π–π [ring centroid(C4–C9)···ring centroid(C4–C9)ⁱ distance = 3.6089 (10) Å for i: 1-x, 1-y, 2-z] interactions feature in the crystal packing. Thus, centrosymmetrically related molecules are connected via π–π interactions, and these are linked into a supramolecular chain via C–H···π contacts, Fig. 2.

Related literature top

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 top

A mixture of racemic erythro mefloquinium chloride (1 mmol) and 2-hydroxybenzoic acid (1 mmol) in acetone (20 ml) was refluxed for 3 h. The reaction mixture was rotary evaporated and the residue was taken up in isopropanol. Two crops of crystals were collected on maintaining the solution at room temperature. From the second crop, on recrystallisation from EtOH, a small amount of the title compound was obtained, m.p. 424–426 K.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of a supramolecular chain in (I) aligned along the a axis. The C–H···π and π–π interactions are shown as brown and purple dashed lines, respectively. Colour code: F, cyan; O, red; N, blue; C, grey; and H, green.

4-(3,3-Dimethylperhydro-1,3-oxazolo[3,4-a]pyridin-1-yl)-2,8- bis(trifluoromethyl)quinoline top

Crystal data top

C₂₀H₂₀F₆N₂O	Z = 2
M_r = 418.38	F(000) = 432
Triclinic, P1	D_x = 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

Data collection top

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 monochromator	R_int = 0.045
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.4°, θ_min = 3.0°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −11→11
T_min = 0.643, T_max = 0.746	l = −16→16
16907 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0739P)² + 0.249P] where P = (F_o² + 2F_c²)/3
4275 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₀H₂₀F₆N₂O	γ = 78.804 (2)°
M_r = 418.38	V = 941.78 (6) Å³
Triclinic, P1	Z = 2
a = 8.4192 (3) Å	Mo Kα radiation
b = 9.1833 (4) Å	µ = 0.13 mm⁻¹
c = 12.4424 (4) Å	T = 120 K
α = 87.912 (2)°	0.65 × 0.30 × 0.25 mm
β = 86.666 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	4275 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	3107 reflections with I > 2σ(I)
T_min = 0.643, T_max = 0.746	R_int = 0.045
16907 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
4275 reflections	Δρ_min = −0.36 e Å⁻³
264 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀F₆N₂O
M_r	418.38
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.4192 (3), 9.1833 (4), 12.4424 (4)
α, β, γ (°)	87.912 (2), 86.666 (2), 78.804 (2)
V (Å³)	941.78 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.65 × 0.30 × 0.25

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.643, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	16907, 4275, 3107
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.141, 1.06
No. of reflections	4275
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.36

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES and FAPEMIG (Brazil).

References

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Volume 66| Part 3| March 2010| Pages o700-o701

doi:10.1107/S1600536810006562

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(3,3-Di­methyl­perhydro-1,3-oxa­zolo[3,4-a]pyridin-1-yl)-2,8-bis­­(tri­fluoro­meth­yl)quinoline

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-(3,3-Dimethylperhydro-1,3-oxazolo[3,4-a]pyridin-1-yl)-2,8-bis(trifluoromethyl)quinoline