2-(2-Chloro-6,7-dimethyl­quinolin-3-yl)-2,3-dihydro­quinolin-4(1H)-one

Saida Benzerka; Abdelmalek Bouraiou; Sofiane Bouacida; Thierry Roisnel; Ali Belfaitah

doi:10.1107/S1600536811028170

. 2011 Jul 23;67(Pt 8):o2084–o2085. doi: 10.1107/S1600536811028170

2-(2-Chloro-6,7-dimethylquinolin-3-yl)-2,3-dihydroquinolin-4(1H)-one

Saida Benzerka ^a, Abdelmalek Bouraiou ^b, Sofiane Bouacida ^b,^*, Thierry Roisnel ^c, Ali Belfaitah ^a

PMCID: PMC3213526 PMID: 22091105

Abstract

In the title molecule, C₂₀H₁₇ClN₂O, the dihedral angle between the mean plane of the quinoline ring system and the benzene ring of the dihydroquinolinone moiety is 57.84 (8)°. In the crystal, molecules are linked into centrosymmetric dimers via pairs of intermolecular N—H⋯N hydrogen bonds. These dimers are further stabilized by weak π–π stacking interactions between pyridine rings with a centroid–centroid distance of 3.9414 (12) Å.

Related literature

For quinoline compounds and their applications, see: Prakash et al. (1994 ▶); Singh & Kapil (1993 ▶); Kalinin et al. (1992 ▶); Xia et al. (1992 ▶); Donnelly & Farrell (1990a ▶,b ▶); Kumar et al. (2004 ▶); Varma & Saini (1997 ▶); Tokes & Litkei (1993 ▶); Tokes & Szilagyi (1987 ▶); Tokes et al. (1992 ▶). For our previous work on quinoline derivatives, see: Belfaitah et al. (2006 ▶); Bouraiou et al. (2008 ▶, 2010 ▶, 2011 ▶); Benzerka et al. (2010 ▶); Ladraa et al. (2010 ▶).

Experimental

Crystal data

C₂₀H₁₇ClN₂O
M _r = 336.81
Triclinic,
a = 7.7345 (4) Å
b = 10.6196 (6) Å
c = 11.3463 (4) Å
α = 96.425 (2)°
β = 100.068 (3)°
γ = 109.576 (1)°
V = 849.84 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 K
0.15 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
7058 measured reflections
3863 independent reflections
2507 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.133
S = 1.00
3863 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811028170/lh5284sup1.cif

e-67-o2084-sup1.cif^{(19.6KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536811028170/lh5284globalsup2.cml

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
N2—H2N⋯N1ⁱ	0.86 (2)	2.53 (2)	3.297 (2)	148.6 (18)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to all personnel of the PHYSYNOR laboratory, Université Mentouri-Constantine, Algeria, for their assistance. Thanks are due to the MESRS (Ministére de l’Enseignement Supérieur et de la Recherche Scientifique - Algeria) for financial support.

supplementary crystallographic information

Comment

2-Phenyl-2,3-dihydroquinolin-4(1H)-one compound substituted on the aromatic rings are valuable precursors (Prakash et al., 1994; Singh & Kapil, 1993) for the synthesis of medicinally important compounds, which are often not readily accessible by other means (Kalinin et al., 1992; Xia et al., 1992). The formation of 2,3-dihydroquinolin-4(1H)-ones is generally accomplished by acid- or base-catalyzed isomerization of substituted 2'-aminochalcones (Donnelly & Farrell, 1990a,b; Tokes & Litkei, 1993). Most of the procedures involve the use of corrosive reagents such as orthophosphoric acid, acetic acid or strong alkali. Many attempts have been made to explore efficient catalysts to accelerate this kind of reaction. Some of them are of limited synthetic scope due to low yields, long reaction times and the need for large amount of catalyst, specialized solvents or microwave activation (Tokes & Szilagyi, 1987; Tokes et al., 1992; Kumar et al. 2004; Varma & Saini, 1997). In continuation of our studies on quinoline derivatives and their biological activities (Bouraiou et al., 2010; Benzerka et al., 2010; Ladraa et al., 2010) we report herein the synthesis and structure determination of 2-(2-chloro-6,7-dimethylquinolin-3-yl)-2,3-dihydroquinolin-4(1H)-one I (Bouraiou et al., 2011). Characterization of the compound I was made from its spectral data (¹H-NMR, ¹³C-NMR), and was unequivocally established from an X-ray crystallographic determination (I).

The molecular structure of (I) is shown in Fig. 1. The two rings of quinolyl moiety are fused in an axial fashion and form a dihedral angle of 0.28 (7)° and this quasi plane system forms dihedral angles of 57.84 (8)° with the benzene ring (C15-C20). The geometric parameters of (I) are in agreement with those of other structures possessing a quinolyl substituent previously reported in the literature (Belfaitah et al., 2006; Bouraiou et al., 2008; Bouraiou et al., 2011). In the crystal, molecules are linked into centrosymmetric dimers via pairs of intermolecular N–H···N hydrogen bonds (Fig. 2). These dimers are further stabilized by π–π stacking interactions between pyridine rings with a centroid to centroid distance of 3.9414 (12)Å.

Experimental

A mixture of (E)-1-(2-aminophenyl)-3-(2-chloro-6,7-dimethylquinolin-3-yl)prop-2-en-1-one and silica gel (1 g) impregnated with indium (III) chloride (20 mol%) was irradiated in domestic microwave oven at 360 W for 5 minutes (Bouraiou et al., 2011). Under these conditions, compound (I) was successfully synthesized in good yield (63%). A suitable crystal of title compound were obtained by crystallization from a CH₂Cl₂/di-isopropylether solution.