1-[(2-Chloro-7,8-dimethyl­quinolin-3-yl)meth­yl]pyridin-2(1H)-one

F Nawaz Khan; S Mohana Roopan; Venkatesha R Hathwar; Mehmet Akkurt

doi:10.1107/S1600536810011505

. 2010 Mar 31;66(Pt 4):o1001. doi: 10.1107/S1600536810011505

1-[(2-Chloro-7,8-dimethylquinolin-3-yl)methyl]pyridin-2(1H)-one

F Nawaz Khan ^a, S Mohana Roopan ^a, Venkatesha R Hathwar ^b, Mehmet Akkurt ^c,^*

PMCID: PMC2983804 PMID: 21580566

Abstract

In the title compound, C₁₇H₁₅ClN₂O, the quinoline ring system is nearly planar, with a maximum deviation from the mean plane of 0.074 (2) Å, and makes a dihedral angle of 81.03 (7)° with the pyridone ring. The crystal packing is stabilized by π–π stacking interactions between the pyridone and benzene rings of the quinoline ring system [centroid–centroid distance = 3.6754 (10) Å]. Furthermore, weak intermolecular C—H⋯O hydrogen bonding links molecules into supramolecular chains along [001].

Related literature

For 2-pyridone analogues, see: Arman et al. (2009 ▶); Clegg & Nichol (2004 ▶); Nichol & Clegg (2005 ▶). For alkaloid analogues of natural or synthetic anticancer agents, see: Roopan & Khan (2009 ▶). For N-alkylation in organic synthesis, see: Roopan et al. (2010 ▶).

Experimental

Crystal data

C₁₇H₁₅ClN₂O
M _r = 298.76
Monoclinic,
a = 7.07034 (17) Å
b = 15.4729 (4) Å
c = 13.1704 (3) Å
β = 96.342 (2)°
V = 1432.01 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 295 K
0.24 × 0.15 × 0.12 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T _min = 0.953, T _max = 0.968
15150 measured reflections
2810 independent reflections
2008 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.108
S = 1.06
2810 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011505/xu2741sup1.cif

e-66-o1001-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011505/xu2741Isup2.hkl

e-66-o1001-Isup2.hkl^{(135.2KB, 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
C12—H12⋯O1ⁱ	0.93	2.52	3.318 (2)	143

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the FIST–DST program at SSCU, IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

Compounds found in nature display a wide range of diversity in terms of their structures and physical and biological properties. Several alkaloid analogues of natural or synthetic anticancer agents (Roopan & Khan, 2009) are well known, and have attracted considerable interest because of their significant activity. Particularly, five and six membered heterocyclic compounds containing one or two hetero atoms fused to a quinoline ring are found in natural products. The search for new anticancer drugs from nature continues to be a fruitful activity, as evidenced by the successes of natural products as pharmaceutical agents. Nitrogen containing heterocyclic compounds, recognized pharmacophores has received great attention in drug discovery and lead optimization. The chemistry of N-alkylation has recently received much attention due to their usefulness as building blocks in organic synthesis (Roopan et al., 2010). On the basis of the interesting structures and biological activities exhibited by several heterocyclic systems possessing quinoline and pyridone nucleus, we have synthesized a quinoline coupled pyridone, i.e., 1-[(2-chloroquinolin-3yl)-methyl]-pyridine-2(1H)-one.

In the title molecule, Fig.1., the quinoline unit is nearly planar, with maximum deviations from the mean plane of -0.074 (2) Å for C2, -0.061 (2) Å for C6 and 0.059 (1) Å for N1 and 0.049 (2) Å for C4. The dihedral angle between the pyridine ring and the quinoline fused-ring system is 81.03 (7)°. Molecular conformation is stabilized by the intra molecular C—H···N and C—H···Cl interactions, forming a 5-membered ring. The crystal structure shows the presence of intermolecular π-π interactions between the pyridone (N2/C11–C15) and benzene (C4–C9) rings of the quinoline ring system, with the Cg2···Cg3(x, 1/2-y, 1/2+z) distance of 3.6754 (10) Å [Cg2 and Cg3 are the centroids of the N2/C11–C15 pyridone and C4–C9 benzene rings, respectively]. The molecular packing is further stabilized by weak intermolecular C—H···O interactions (Table1, Fig. 2), forming chains in the [001] direction.

Experimental

To a mixed well solution of 2-pyridone (95 mg, 1 mmol, in 2 ml of DMF), KO^tBu (112 mg, 1 mmol in 10 ml of THF) and 2-chloro-3-(chloromethyl)-7,8-dimethylquinoline (240 mg, 1 mmol) were added and the resulting mixture was refluxed at 343 K for 1 h. After the completion of the reaction, cooled and removed the excess of solvent under reduced pressure. Crushed ice was mixed with the residue. White solid was formed, filtered and dried, purified by column chromatography using hexane and ethylacetate as the eluant. Crystals of suitable quality were grown by solvent evaporation from a solution of the compound in chloroform.