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

Khan, F.N.; Roopan, S.M.; Hathwar, V.R.; Akkurt, M.

doi:10.1107/S1600536810011505

Volume 66
Part 4
Page o1001
April 2010

Received 24 March 2010
Accepted 26 March 2010
Online 31 March 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.108
Data-to-parameter ratio = 14.6
Details

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 and Mehmet Akkurt ^c ^*

^aOrganic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India,^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

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 [pi] - [pi] stacking interactions between the pyridone and benzene rings of the quinoline ring system [centroid-centroid distance = 3.6754 (10) Å]. Furthermore, weak intermolecular C-HO 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, P 2₁ /c
a = 7.07034 (17) Å
b = 15.4729 (4) Å
c = 13.1704 (3) Å
= 96.342 (2)°
V = 1432.01 (6) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.953, T_max = 0.968
15150 measured reflections
2810 independent reflections
2008 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.108
S = 1.06
2810 reflections
192 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O1ⁱ	0.93	2.52	3.318 (2)	143
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: XU2741 ).

Acknowledgements

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.

References

Arman, H. D., Poplaukhin, P. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o3187.
Clegg, W. & Nichol, G. S. (2004). Acta Cryst. E60, o1433-o1436.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Nichol, G. S. & Clegg, W. (2005). Acta Cryst. C61, o383-o385.
Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.
Roopan, S. M. & Khan, F. N. (2009). ARKIVOC, pp. 161-169.
Roopan, S. M., Khan, F. N. & Mandal, B. K. (2010). Tetrahedron Lett. doi:org/10.1016/j.tetlet.2010.02.128.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds