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Volume 69 
Part 9 
Page o1393  
September 2013  

Received 28 July 2013
Accepted 1 August 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.095
Data-to-parameter ratio = 14.9
Details
Open access

(2E)-3-(2-Chlorobenzo[h]quinolin-3-yl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one

aDepartment of Chemistry, BITS, Pilani - K. K. Birla Goa Campus, Goa 403 726, India,bCentre for Organic and Medicinal Chemistry, 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 title compound, C32H21ClN2O, an almost planar (r.m.s. deviation = 0.033 Å) prop-2-en-1-one bridge links quinolinyl and benzoquinolinyl residues; the latter are twisted out of the plane of the bridge [dihedral angles = 75.94 (5) and 20.20 (5)°, respectively]. In the crystal, a three-dimensional architecture arises as a result of C-H...O, C-H...[pi] and [pi]-[pi] [centroid-centroid distances involving pyridine rings = 3.5806 (7)-3.7537 (7) Å] interactions.

Related literature

For biological applications of quinoline derivatives, see: Jörg et al. (2007[Jörg, W., Daniela, G. & Gerhard, R. (2007). Inorg. Chim. Acta, 360, 1935-1942.]); Prasath et al. (2013a[Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2013a). J. Organomet. Chem. 726, 62-70.]). For a related structure, see: Prasath et al. (2013b[Prasath, R., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2013b). Acta Cryst. E69, o1275.]).

[Scheme 1]

Experimental

Crystal data
  • C32H21ClN2O

  • Mr = 484.96

  • Triclinic, [P \overline 1]

  • a = 7.1354 (3) Å

  • b = 10.1627 (5) Å

  • c = 17.0127 (8) Å

  • [alpha] = 78.758 (4)°

  • [beta] = 79.544 (4)°

  • [gamma] = 84.042 (4)°

  • V = 1186.91 (9) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 1.65 mm-1

  • T = 100 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.870, Tmax = 1.000

  • 8673 measured reflections

  • 4849 independent reflections

  • 4433 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.095

  • S = 1.04

  • 4849 reflections

  • 326 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1-pyridyl ring.

D-H...A D-H H...A D...A D-H...A
C10-H10C...O1i 0.98 2.54 3.4116 (18) 148
C15-H15...Cg1ii 0.95 2.65 3.4695 (15) 145
Symmetry codes: (i) -x, -y, -z+2; (ii) x-1, y, 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: PV2642 ).


Acknowledgements

RP gratefully acknowledges the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship (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 (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.  [ISI] [CrossRef] [ChemPort] [details]
Jörg, W., Daniela, G. & Gerhard, R. (2007). Inorg. Chim. Acta, 360, 1935-1942.
Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2013a). J. Organomet. Chem. 726, 62-70.  [CSD] [CrossRef] [ChemPort]
Prasath, R., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2013b). Acta Cryst. E69, o1275.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1393  [ doi:10.1107/S1600536813021545 ]

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