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Volume 69 
Part 8 
Page o1275  
August 2013  

Received 12 July 2013
Accepted 13 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.095
Data-to-parameter ratio = 14.9
Details
Open access

(2E)-3-(2-Chloro-8-methylquinolin-3-yl)-1-(2,4-dimethylquinolin-3-yl)prop-2-en-1-one

aDepartment of Chemistry, BITS, Pilani - K. K. Birla Goa Campus, Goa 403 726, India,bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the molecule of the title compound, C24H19ClN2O, the terminal quinolinyl residues are close to perpendicular to each other [dihedral angle 83.72 (4)°]. The quinolinyl residues are connected by and inclined to the prop-2-en-1-one bridge, with the Car-Car-C-C (ar = aromatic) torsion angles being 71.01 (17) and 20.6 (2)°. The crystal structure features phenyl-carbonyl C-H...O interactions and [pi]-[pi] interactions between centrosymmetrically related quinolinyl residues [3.5341 (10) and 3.8719 (9) Å], which together lead to a three-dimensional architecture.

Related literature

For background to quinoline chalcones and for a related structure, see: Prasath et al. (2013[Prasath, R., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o1274.]).

[Scheme 1]

Experimental

Crystal data
  • C24H19ClN2O

  • Mr = 386.86

  • Triclinic, [P \overline 1]

  • a = 7.4150 (5) Å

  • b = 9.9045 (6) Å

  • c = 14.0696 (9) Å

  • [alpha] = 71.072 (5)°

  • [beta] = 88.427 (5)°

  • [gamma] = 72.552 (5)°

  • V = 929.66 (10) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 1.95 mm-1

  • T = 100 K

  • 0.25 × 0.25 × 0.25 mm

Data collection
  • Agilent SuperNova Dual diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.853, Tmax = 1.000

  • 6846 measured reflections

  • 3811 independent reflections

  • 3587 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.095

  • S = 1.04

  • 3811 reflections

  • 256 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20...O1i 0.95 2.58 3.364 (2) 140
Symmetry code: (i) x-1, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7108 ).


Acknowledgements

RP gratefully acknowledges the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship [grant No. 09/919/(0014)/2012 EMR-I]. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM·C/HIR-MOHE/SC/03).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Prasath, R., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o1274.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1275  [ doi:10.1107/S1600536813019405 ]

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