4-Chloro-6-methyl-N-(4-methyl­phen­yl)quinolin-2-amine

K N Vennila; K Prabha; M Manoj; K J Rajendra Prasad; D Velmurugan

doi:10.1107/S1600536811002327

. 2011 Jan 26;67(Pt 2):o490. doi: 10.1107/S1600536811002327

4-Chloro-6-methyl-N-(4-methylphenyl)quinolin-2-amine

K N Vennila ^a, K Prabha ^b, M Manoj ^b, K J Rajendra Prasad ^b, D Velmurugan ^a,^*

PMCID: PMC3051802 PMID: 21523146

Abstract

In the title compound C₁₇H₁₅ClN₂, the dihedral angle between the quinoline ring system and the phenyl ring is 50.18 (6)°. In the crystal, molecules are linked into chains running along the c axis by N—H⋯N hydrogen bonds.

Related literature

For the biological activity of quinoline derivatives, see: Lunniss et al. (2009 ▶); Kemnitzer et al. (2008 ▶); Woodrow et al. (2009 ▶). For a related structure, see: Cheng et al. (2005 ▶). For the synthesis, see: Manoj et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₁₅ClN₂
M _r = 282.76
Monoclinic,
a = 15.1445 (13) Å
b = 11.4337 (10) Å
c = 8.4764 (7) Å
β = 92.344 (4)°
V = 1466.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.22 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
13649 measured reflections
3669 independent reflections
2508 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.125
S = 1.03
3669 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002327/bt5456sup1.cif

e-67-0o490-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002327/bt5456Isup2.hkl

e-67-0o490-Isup2.hkl^{(179.9KB, 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
N2—H2⋯N1ⁱ	0.86	2.59	3.404 (2)	157

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Symmetry code: (i) Inline graphic .

Acknowledgments

KNV thanks the CSIR, New Delhi, for financial assistance in the form of a Senior Research fellowship. DV acknowledges the Department of Science and Technology (DST) for providing data-collection facilities under the TBI Program and is also grateful for financial support to the Department under the UGC–SAP and DST–FIST programs.

supplementary crystallographic information

Comment

Quinoline derivatives fused with various heterocycles have displayed potent anticancer activity targeting different sites like topoisomerase I, telomerase, farnasyl transferase, Src tyrosine kinase, protein kinase CK-II etc. The trisubstituted quinoline analogs have attractive profile and are a good start point to initiate a lead optimisation programme. Due to its significant biological importance, the title compound was chosen for the X-ray crystallographic study.

The title compound is the first structural example with methyl phenyl moiety attached to the amino substituted quinoline. The chlorine atom deviates only by 0.0276 (5)Å below the mean plane of atoms passing through C2-C10, N1. The methyl phenyl moiety is oriented at 129.9 (5)° from the plane containing the quinoline ring system.

C-H···N and N-H···N intermolecular interactions assist the molecular packing of the crystal which resembles helical patterns. In addition to van der Waals forces, the hydrogen bond interactions at the groove of helix maintains the stability of the crystal packing. Atom N1 acts as a bifurcated acceptor. The bifurcated hydrogen bond also forms the R₁²(6) motif. The structure of the title compound is shown in Figure 1. All the bond lengths and bond angles are in the usual ranges. The molecular packing with hydrogen bonds as dotted lines is shown in Figure 2.

Experimental

A mixture of appropriate 6-methyl-2,4-dichloroquinoline (0.010 mol) and p-toluidine (0.010 mol) was heated under neat condition at 160°C for half an hour. The product obtained was washed with water, dried and purified by column chromatography over silica gel and eluted with petroleum ether : ethyl acetate mixture (99 : 1) to get the product as pale yellow solid. It was recrystallised using methanol.