{5-Methyl-1-[8-(trifluoro­meth­yl)quinolin-4-yl]-1H-1,2,3-triazol-4-yl}(morpholino)methanone

N Anuradha; A Thiruvalluvar; M Mahalinga; R J Butcher

doi:10.1107/S1600536808037562

. 2008 Nov 20;64(Pt 12):o2375. doi: 10.1107/S1600536808037562

{5-Methyl-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-1,2,3-triazol-4-yl}(morpholino)methanone

N Anuradha ^a, A Thiruvalluvar ^a,^*, M Mahalinga ^b, R J Butcher ^c

PMCID: PMC2959961 PMID: 21581347

Abstract

In the title molecule, C₁₈H₁₆F₃N₅O₂, the dihedral angle between the pyridine ring and the fused benzene ring is 4.50 (10)°. The triazole ring makes dihedral angles of 54.48 (12) and 57.91 (11)° with the pyridine and benzene rings, respectively. The morpholine ring atoms are disordered over two positions; the site-occupancy factors are ca 0.53 and 0.47. Intermolecular C—H⋯F hydrogen bonding is found in the crystal structure. Furthermore, C—H⋯O and C—H⋯N intramolecular contacts are also present.

Related literature

For the uses of 1,2,3-triazoles and their benzo derivatives, see: Sanghvi et al. (1990 ▶). For a related crystal structure, see: Thiruvalluvar et al. (2007 ▶).

Experimental

Crystal data

C₁₈H₁₆F₃N₅O₂
M _r = 391.36
Triclinic,
a = 9.2836 (15) Å
b = 9.6164 (11) Å
c = 9.9272 (11) Å
α = 92.082 (9)°
β = 93.063 (11)°
γ = 105.728 (12)°
V = 850.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 200 (2) K
0.53 × 0.28 × 0.22 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T _min = 0.934, T _max = 0.973
10917 measured reflections
5503 independent reflections
2919 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.077
wR(F ²) = 0.262
S = 1.02
5503 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037562/bq2106sup1.cif

e-64-o2375-sup1.cif^{(30.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037562/bq2106Isup2.hkl

e-64-o2375-Isup2.hkl^{(264KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯F1ⁱ	0.95	2.35	3.237 (3)	156
C16—H16B⋯O1	0.98	2.44	3.012 (3)	117
C23A—H23B⋯O1	0.99	2.36	2.812 (5)	107
C25A—H25A⋯N13	0.99	2.25	2.893 (5)	122

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Symmetry code: (i) Inline graphic .

Acknowledgments

AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007]. RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer.

supplementary crystallographic information

Comment

1,2,3-Triazoles and their benzo derivatives have attracted considerable attention because of their theoretical interest and synthetic value. They also find numerous applications in industry and agriculture due to their extensive biological activities and successful application as fluorescent whiteners, light stabilizers and optical brightening agents (Sanghvi et al., 1990). Thiruvalluvar et al. (2007) have reported the crystal structure of 1-{5-Methyl-1-[8-(trifluoromethyl)-quinolin-4-yl]-1H-1,2,3-triazol-4-yl}- ethanone.

In the title molecule, C₁₈H₁₆F₃N₅O₂, Fig.1., the quinoline unit is nearly planar. The dihedral angle between the pyridine ring and the fused benzene ring is 4.50 (10)°. The triazole ring makes a dihedral angle of 54.48 (12)° and 57.91 (11)°, with that of pyridine and benzene rings, respectively. The trifluoromethyl group is coplanar with the attached benzene ring, except the fluoro atoms. The disordered morpholine ring is in chair form. Intermolecular C3—H3···F1(1 + x, y, z) hydrogen bond is found in the crystal structure. Further, C7—H7···F1, C16—H16B···O1, C23A—H23B···O1 and C25A—H25A···N13 intramolecular contacts are also found(Fig.2., Table 1).

Experimental

5-Methyl-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-1,2,3-triazole-4-carboxylic acid(10 g, 0.031 mol) was treated with thionyl chloride (3.7 g, 0.031 mol) in chlorofor (75 ml) and the mixture was heated to reflux for 2 h. The solvent was distilled out completely under vacuum. The residue was diluted with dry tetra hydrofuran (50 ml) and cooled to 273 K. This mixture was added slowly to the previously cooled morpholine in dry tetra hydrofuran (50 ml). Stirred for 1 h at 298 K and quenched to ice cooled water (500 ml). The precipitated solids were filtered, washed with water. The crude product was recrystallized from methanol. Yield 7.5 g (61.9%).