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

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

doi:10.1107/S1600536812043954

Volume 68
Part 11
Page o3250
November 2012

Received 13 October 2012
Accepted 23 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.057
wR = 0.168
Data-to-parameter ratio = 14.9
Details

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

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

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

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 [pi] - [pi] 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, P 2₁ /c
a = 7.982 (3) Å
b = 17.921 (6) Å
c = 12.478 (4) Å
= 92.581 (6)°
V = 1783.1 (11) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.168
S = 1.04
3392 reflections
228 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.45 e Å^-3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2238 ).

Acknowledgements

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

References

Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Badahdah, K. O. & Ng, S. W. (2011). Acta Cryst. E67, o2596.
Balasubramanian, M., Keay, J. G., Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). Comprehensive Heterocyclic Chemistry II, Vol. 5, p. 245. Oxford: Pergamon Press.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Michael, J. P. (1997). Nat. Prod. Rep. 14, 605-608.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds