1-[(2-Chloro-8-methyl­quinolin-3-yl)­meth­yl]pyridin-2(1H)-one

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

doi:10.1107/S1600536810012730

Volume 66
Part 5
Page o1049
May 2010

Received 24 March 2010
Accepted 6 April 2010
Online 10 April 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.034
wR = 0.100
Data-to-parameter ratio = 13.8
Details

1-[(2-Chloro-8-methylquinolin-3-yl)methyl]pyridin-2(1H)-one

Atul Kumar Kushwaha,^a S. Mohana Roopan,^a F. Nawaz Khan,^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, C₁₆H₁₃ClN₂O, the quinoline ring system is approximately planar [maximum deviation 0.021 (2) Å] and forms a dihedral angle of 85.93 (6)° with the pyridone ring. Intermolecular C-HO hydrogen bonding, together with weak C-H [pi] and [pi] - [pi] interactions [centroid-to-centroid distances 3.5533 (9) and 3.7793 (9) Å], characterize the crystal structure.

Related literature

For 2-pyridone analogues, see: Arman et al. (2009); Clegg & Nichol (2004); Nichol & Clegg (2005). For the synthesis of 2-pyridone derivatives, see: Banerjee & Sereda (2009); Roopan & Khan (2009); Roopan et al. (2010); Dandepally & Williams (2009).

Experimental

Crystal data

C₁₆H₁₃ClN₂O
M_r = 284.73
Monoclinic, P 2₁ /c
a = 10.1513 (2) Å
b = 9.3917 (2) Å
c = 14.1430 (2) Å
= 90.948 (2)°
V = 1348.17 (4) Å³
Z = 4
Mo K radiation
= 0.28 mm^-1
T = 295 K
0.26 × 0.24 × 0.20 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.931, T_max = 0.946
17649 measured reflections
2511 independent reflections
2088 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.100
S = 1.10
2511 reflections
182 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1-C3/C8/C9 ring.

D-HA	D-H	HA	DA	D-HA
C11-H11O1ⁱ	0.93	2.54	3.286 (2)	137
C6-H6Cg1ⁱⁱ	0.93	2.61	3.4457 (18)	150
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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: 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: IM2191 ).

Acknowledgements

The authors thank the FIST programme for the data collection on the Oxford single-crystal diffractometer at SSCU, IISc, Bangalore. We also 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.
Banerjee, S. & Sereda, G. (2009). Tetrahedron Lett. 50, 6959-6962.
Clegg, W. & Nichol, G. S. (2004). Acta Cryst. E60, o1433-o1436.
Dandepally, S. R. & Williams, A. L. (2009). Tetrahedron Lett. 50, 1395-1398.
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. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Roopan, S. M. & Khan, F. N. (2009). ARKIVOC, xiii, 161-169.
Roopan, S. M., Khan, F. N. & Mandal, B. K. (2010). Tetrahedron Lett. 51, 2309-2311.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds