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Volume 69 
Part 9 
Page o1463  
September 2013  

Received 15 August 2013
Accepted 19 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.125
Data-to-parameter ratio = 18.2
Details
Open access

6-Chloro-2-(4-methoxyphenyl)-4-phenylquinoline

aCentre for Research and Development, PRIST University, Vallam, Thanjavur 613 403, India,bDepartment of Chemistry, DDE, Alagappa University, Karaikudi 630 003, India, and cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
Correspondence e-mail: chakkaravarthi_2005@yahoo.com, crystallography2010@gmail.com

In the title compound, C22H16ClNO, the quinoline ring system makes dihedral angles of 56.30 (6) and 7.93 (6)°, respectively, with the adjacent phenyl and benzene rings. The dihedral angle between these phenyl and benzene rings is 56.97 (8)°. In the crystal, weak C-H...[pi] and [pi]-[pi] [centroid-centroid distances of 3.7699 (9) and 3.8390 (9) Å] interactions link the molecules into a layer parallel to the ab plane.

Related literature

For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For a related structure, see: Akkurt et al. (2004[Akkurt, M., Öztürk, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2004). Acta Cryst. E60, o1266-o1268.]).

[Scheme 1]

Experimental

Crystal data
  • C22H16ClNO

  • Mr = 345.81

  • Monoclinic, P 21 /n

  • a = 10.5922 (5) Å

  • b = 8.2883 (3) Å

  • c = 19.1885 (9) Å

  • [beta] = 92.988 (3)°

  • V = 1682.29 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 295 K

  • 0.40 × 0.36 × 0.34 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.912, Tmax = 0.924

  • 12611 measured reflections

  • 4148 independent reflections

  • 3244 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.125

  • S = 1.03

  • 4148 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C10-C15 and C16-C19 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C14-H14...Cg4i 0.93 2.63 3.7695 (19) 151
C22-H22B...Cg3ii 0.96 2.84 3.613 (3) 138
Symmetry codes: (i) x-1, y, z; (ii) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5297 ).


Acknowledgements

The authors acknowledge the STIC, Cochin University of Technology, Cochin, for the data collection. VT and NS also acknowledge the UGC [project 40-46/2011 (SR)], New Delhi.

References

Akkurt, M., Öztürk, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2004). Acta Cryst. E60, o1266-o1268.  [CSD] [CrossRef] [ChemPort] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1463  [ doi:10.1107/S1600536813023295 ]

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