2-{1-[2,8-Bis(trifluoro­meth­yl)quinolin-4-yl]-3,5,6,7,8,8a-hexa­hydro-1H-1,3-oxazolo[3,4-a]pyridin-3-yl}phenol

Gonçalves, R.S.B.; Kaiser, C.R.; Souza, M.V.N. de; Wardell, J.L.; Wardell, S.M.S.V.; Tiekink, E.R.T.

doi:10.1107/S1600536811022379

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1656-o1657

doi:10.1107/S1600536811022379

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2-{1-[2,8-Bis(trifluoromethyl)quinolin-4-yl]-3,5,6,7,8,8a-hexahydro-1H-1,3-oxazolo[3,4-a]pyridin-3-yl}phenol

Raoni S. B. Gonçalves,^a,^b Carlos R. Kaiser,^b Marcus V. N. de Souza,^a James L. Wardell,^c ‡ Solange M. S. V. Wardell ^d and Edward R. T. Tiekink ^e ^*

^aFundação Oswaldo Cruz, Instituto de Tecnologia, em Fármacos–Farmanguinhos, R. Sizenando Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil, ^bDepartamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro, Brazil, ^cCentro 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, ^dCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, and ^eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 June 2011; accepted 9 June 2011; online 18 June 2011)

In the title mefloquine–oxazolidine derivative, C₂₄H₂₀F₆N₂O₂, 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 C₆ 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 intramolecular O—H⋯N(piperidine) hydrogen bond is present. The crystal packing features C—H⋯O, C—H⋯F and C—H⋯π(hydroxybenzene) interactions.

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_r = 482.42
Orthorhombic, F d d 2
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.082
S = 1.10
2660 reflections
308 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[-x+2, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 4}}, -y+{\script{7\over 4}}, z+{\script{3\over 4}}]$ ; (iii) $[x-{\script{1\over 4}}, -y+{\script{7\over 4}}, z+{\script{1\over 4}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022379/hb5905sup1.cif

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

checkCIF report

Comment top

A recent publication reported the synthesis and anti-tubercular activity of mefloquine-oxazolidine derivatives (Gonçalves et al., 2010). Subsequently, crystals became available for one of the derivatives, the title compound (I), allowing full characterization by X-ray crystallography.

In (I), Fig. 1, the oxazoline ring adopts an envelope conformation with the flap atom being N2 as seen in the puckering parameters Q(2) = 0.409 (2) Å and ϕ₂ = 100.6 (3) ° (Cremer & Pople, 1975). The piperidinyl ring is close to a chair conformation with puckering parameters: Q(2) = 0.060 (3) Å and Q(3) = -0.596 (3) Å, and amplitudes: Q = 0.599 (3) Å, θ = 174.6 (3) ° and ϕ = 214 (3) ° (Cremer & Pople, 1975). The 10 non-hydrogen atom comprising the quinoline residue are co-planar with the r.m.s. deviation being 0.025 Å. With reference to this plane, the oxazolidine residue, with the exception of the O1 atom, lies to one side of the plane. By contrast, the benzene ring is somewhat splayed [forming a dihedral angle of 50.34 (11) °] with half the ring above and the other half below the plane through the quinoline atoms. The oxazolidine and benzene ring are directed away from the C₆ ring of the quinoline residue, and the hydroxyl group is orientated to allow the formation of a O—H···N hydrogen bond, Table 1.

Molecules are stabilized in the crystal structure by a combination of C—H···O, C—H···F and C—H···π(hydroxybenzene) interactions, Table 1 and Fig. 2.

Related literature top

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 top

The compound was prepared as reported in the literature (Gonçalves et al., 2010) and was recrystallized from its ethanol solution for the structural study.

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: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the c axis of the unit-cell contents of (I) with the C—H···O, C—H···F and C—H···π(hydroxybenzene) interactions shown as orange blue and purple dashed lines, respectively.

2-{1-[2,8-Bis(trifluoromethyl)quinolin-4-yl]-3,5,6,7,8,8a-hexahydro- 1H-1,3-oxazolo[3,4-a]pyridin-3-yl}phenol top

Crystal data top

C₂₄H₂₀F₆N₂O₂	F(000) = 3968
M_r = 482.42	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0295P)² + 15.365P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
2660 reflections	Δρ_max = 0.20 e Å⁻³
308 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₄H₂₀F₆N₂O₂	V = 8783.5 (5) Å³
M_r = 482.42	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 27.2766 (11) Å	µ = 0.13 mm⁻¹
b = 34.1005 (9) Å	T = 120 K
c = 9.4431 (2) Å	0.40 × 0.20 × 0.16 mm

Data collection top

Enraf–Nonius KappaCCD diffractometer	2660 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2519 reflections with I > 2σ(I)
T_min = 0.799, T_max = 1.000	R_int = 0.043
13970 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0295P)² + 15.365P] where P = (F_o² + 2F_c²)/3
S = 1.10	Δρ_max = 0.20 e Å⁻³
2660 reflections	Δρ_min = −0.24 e Å⁻³
308 parameters	Absolute structure: nd
1 restraint

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	0.98349 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+3/2, z+1/2; (ii) x+1/4, −y+7/4, z+3/4; (iii) x−1/4, −y+7/4, z+1/4.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀F₆N₂O₂
M_r	482.42
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	120
a, b, c (Å)	27.2766 (11), 34.1005 (9), 9.4431 (2)
V (Å³)	8783.5 (5)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.40 × 0.20 × 0.16

Data collection
Diffractometer	Enraf–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.799, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13970, 2660, 2519
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.082, 1.10
No. of reflections	2660
No. of parameters	308
No. of restraints	1
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0295P)² + 15.365P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24
Absolute structure	Nd

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+3/2, z+1/2; (ii) x+1/4, −y+7/4, z+3/4; (iii) x−1/4, −y+7/4, z+1/4.

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 are gratefully acknowledged. JLW acknowledges support from CAPES (Brazil).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gonçalves, R. S. B., Kaiser, C. R., Lourenço, M. C. S., de Souza, M. V. N., Wardell, J. L., Wardell, S. M. S. V. & da Silva, A. D. (2010). Eur. J. Med. Chem. 45, 6095–6100. Web of Science PubMed Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Pages o1656-o1657

doi:10.1107/S1600536811022379

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

2-{1-[2,8-Bis(tri­fluoro­meth­yl)quinolin-4-yl]-3,5,6,7,8,8a-hexa­hydro-1H-1,3-oxazolo[3,4-a]pyridin-3-yl}phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-{1-[2,8-Bis(trifluoromethyl)quinolin-4-yl]-3,5,6,7,8,8a-hexahydro-1H-1,3-oxazolo[3,4-a]pyridin-3-yl}phenol