Ethyl 2-methyl-4-phenyl­quinoline-3-carboxyl­ate

Ayoob Bazgir

doi:10.1107/S1600536809018625

. 2009 May 23;65(Pt 6):o1382. doi: 10.1107/S1600536809018625

Ethyl 2-methyl-4-phenylquinoline-3-carboxylate

Ayoob Bazgir ^a,^*

PMCID: PMC2969813 PMID: 21583230

Abstract

In the molecule of the title compound, C₁₉H₁₇NO₂, the quinoline ring system is planar [maximum deviation 0.021 (3) Å] and oriented with respect to the phenyl ring at a dihedral angle of 80.44 (4)°. Intramolecular C—H⋯O interactions result in the formation of five- and six-membered rings having planar and envelope conformations, respectively. In the crystal structure, intermolecular C—H⋯O interactions link the molecules into centrosymmetric dimers forming R ₂ ²(12) ring motifs. π–π contacts between the rings of the quinoline system [centroid-to-centroid distance = 3.812 (1) Å] may further stabilize the structure. Two weak C—H⋯π interactions are also found.

Related literature

For general background, see: Doube et al. (1998 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₁₇NO₂
M _r = 291.34
Triclinic,
a = 9.0282 (10) Å
b = 9.362 (1) Å
c = 10.7258 (10) Å
α = 69.765 (8)°
β = 66.733 (8)°
γ = 70.605 (8)°
V = 761.08 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.35 × 0.32 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
8164 measured reflections
3995 independent reflections
3410 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.194
S = 1.09
3995 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018625/hk2681sup1.cif

e-65-o1382-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018625/hk2681Isup2.hkl

e-65-o1382-Isup2.hkl^{(191.8KB, 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
C16—H16A⋯O1	0.97	2.32	2.711 (3)	103
C19—H19B⋯O2ⁱ	0.96	2.52	3.374 (3)	147
C19—H19C⋯O2	0.96	2.59	3.212 (3)	122
C12—H12⋯Cg2ⁱⁱ	0.93	2.95	3.750 (3)	145
C17—H17C⋯Cg3ⁱⁱⁱ	0.96	2.97	3.883 (3)	160

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg2 and Cg3 are the centroids of rings C1–C6 and C8–C13, respectively.

Acknowledgments

The author is grateful to the Islamic Azad University, Dorood Branch, for financial support.

supplementary crystallographic information

Comment

The quinoline moiety is probably the most well known heterocycle, a common and important feature of a variety of natural products and medicinal agents. They have emerged as antimalarial, antiasthmatic, anti-inflamatory, antibacterial, antihypertensive and tyrosine kinase PDGF-RTK inhibiting agents (Doube et al., 1998). Moreover, polyquinolines are found to undergo hierarchical self-assembly into a variety of nano and meso structures with enhanced electronic and photonic functions. We report herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The quinoline ring system A (N1/C1–C7/C14/C18) is planar with a maximum deviaton of -0.021 (3) Å for atom C18, and oriented with respect to the phenyl ring B (C8–C13) at a dihedral angle of A/B = 80.44 (4)°. Intramolecular C—H···O interactions result in the formations of five- and six-membered rings C (O1/O2/C15/C16/H16A) and D (O2/C14/C15/C18/C19/H19C). Ring C is planar, while ring D adopts envelope conformation, with atom O2 displaced by -1.166 (4) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular C—H···O interactions (Table 1) link the molecules into centrosymmetric dimers forming R₂²(12) ring motifs (Fig. 2) (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The π–π contact between the rings of the quinoline ring system, Cg1···Cg2ⁱ [symmetry code: (i) 1 - x, -1 - y, 1 - z, where Cg1 and Cg2 are centroids of the rings (N1/C1/C6/C7/C14/C18) and (C1–C6), respectively] may further stabilize the structure, with centroid-centroid distance of 3.812 (1) Å. There also exist two weak C—H···π interactions (Table 1).

Experimental

For the preparation of the title compound, a mixture of ethyl acetoacetate (0.13 g, 1 mmol), (2-aminophenyl)(phenyl)methanone (0.20 g, 1 mmol) and p-toluene sulfonic acid (0.1 g, 5.8 mmol) in water (5 ml) was stirred at reflux for 4 h. After completion of reaction (monitored by TLC) the reaction mixture was filtered and the precipitate washed with water (15 ml) and then recrystallized from EtOH/water (1:2) to afford the pure product (yield; 75%, 0.218 g).