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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 [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.168
Data-to-parameter ratio = 14.9
Details
Open access

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

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[Michael, J. P. (1997). Nat. Prod. Rep. 14, 605-608.]); Balasubramanian et al. (1996[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.]). For a related structure, see: Asiri et al. (2011[Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Badahdah, K. O. & Ng, S. W. (2011). Acta Cryst. E67, o2596.]).

[Scheme 1]

Experimental

Crystal data
  • C23H18ClN

  • Mr = 343.83

  • Monoclinic, P 21 /c

  • a = 7.982 (3) Å

  • b = 17.921 (6) Å

  • c = 12.478 (4) Å

  • [beta] = 92.581 (6)°

  • V = 1783.1 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.168

  • S = 1.04

  • 3392 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[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.]); 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.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Michael, J. P. (1997). Nat. Prod. Rep. 14, 605-608.  [CrossRef] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3250  [ doi:10.1107/S1600536812043954 ]

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