2-(4-Chloro­phen­yl)-6-methyl-4-(3-methyl­phen­yl)quinoline

M Prabhuswamy; T R Swaroop; S Madan Kumar; K S Rangappa; N K Lokanath

doi:10.1107/S1600536812043954

. 2012 Oct 31;68(Pt 11):o3250. doi: 10.1107/S1600536812043954

2-(4-Chlorophenyl)-6-methyl-4-(3-methylphenyl)quinoline

M Prabhuswamy ^a, T R Swaroop ^b, S Madan Kumar ^a, K S Rangappa ^b, N K Lokanath ^a,^*

PMCID: PMC3515327 PMID: 23284547

Abstract

In the title compound, C₂₃H₁₈ClN, the dihedral angles between the quinoline unit and the chlorobenzene and methylbenzene rings are 2.57 (9) and 56.06 (9)°, respectively. The crystal structure is stabilized by π–π interactions [minimum ring centroid separation = 3.733 (2) Å].

Related literature

For quinolines, see: Michael (1997 ▶); Balasubramanian et al. (1996 ▶). For a related structure, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C₂₃H₁₈ClN
M _r = 343.83
Monoclinic,
a = 7.982 (3) Å
b = 17.921 (6) Å
c = 12.478 (4) Å
β = 92.581 (6)°
V = 1783.1 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.23 × 0.22 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer
16998 measured reflections
3392 independent reflections
2508 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.168
S = 1.04
3392 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(26.6KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043954/zs2238sup1.cif

e-68-o3250-sup1.cif^{(26.6KB, cif)}

Click here for additional data file.^{(166.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043954/zs2238Isup2.hkl

e-68-o3250-Isup2.hkl^{(166.4KB, hkl)}

Click here for additional data file.^{(6.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812043954/zs2238Isup3.cml

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

Acknowledgments

SMK thanks the UGC–BRS and the University of Mysore for the award of a fellowship.

supplementary crystallographic information

Comment

Quinolines and their derivatives occur in numerous natural products (Michael, 1997) and may exhibit interesting physiochemical activities, finding applications as pharmaceuticals and agrochemicals as well as being general synthetic platforms (Balasubramanian et al., 1996).

In the title molecule, C₂₃ H₁₈ Cl N, (Fig. 1), dihedral angles between the quinoline moiety and the chlorobenzene and methylbenzene rings are 2.57 (9) and 56.06 (9)°, respectively, with the conformation of the chlorobenzene ring influenced by the presence of an intramolecular C5—H···N1 interaction [2.764 (3) Å]. The overall geometry of the title compound is similar to 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline -3-carbonitrile (Asiri et al., 2011).

The crystal structure (Fig. 2) is stabilized by aromatic ring π··· π interactions with the ring centroids defined as follows: Cg(1), N1/C7/C8/C9/C10/C15; Cg(2), C1/C2/C3/C4/C5/C6 and Cg(3), C10/C11/C12/C13/C14/C15. The distance between Cg(1) and Cg(1) is 3.7427 (18) Å [-x+3, -y+2, -z+1], Cg(1) and Cg(2) is 3.7679 (19) Å [-x+2,-y+2,1 -z], Cg(1) and Cg(3) is 3.7635 (18) Å [-x+3, -y+2, -z+1], Cg(2) and Cg(3) is 3.733 (2) Å [-x+2, -y+2, -z+1].

Experimental

The enaminone [3-(4-chlorophenyl)-1-m-tolyl-3-(p-tolyamino)prop-2-en-1-one] (5 mmol) was taken in polyphosphoric acid (5 mL) and heated at 140 °C for 5 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (50 mL). The aqueous layer was extracted with ethyl acetate (3 x 20 mL), the combined ethyl acetate layer was washed with 0.1 N NaOH (2 x 25 mL), followed by brine solution (25 mL). The organic layer was then dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product which was purified by column chromatography over silica gel (60–120 mesh) using a hexane:ethyl acetate mixture (9.5:0.5) as eluent. The pure title compound was crystallized in an ethyl acetate–hexane mixture to obtain pale yellow single crystals. ¹H NMR (CDCl₃, 300 MHz): 8.49 (d, 2H, J=8.4 Hz), 7.92 (d, 1H, J=7.2 Hz), 7.79 (s, 1H), 7.55–7.66 (m, 5H), 7.19 (d, 1H), 2.34 (s, 3H), 2.35 (s, 3H). Mass: Calc. 343.2 found 344.2 (M⁺+1): m.p. 98–100 °C (uncorrected).