Received 12 July 2013
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: firstname.lastname@example.org
The molecule of the title compound, C24H19ClN2O2, is bent, with the dihedral angle between the terminal quinoline ring systems being 63.30 (5)°. The quinolinyl residues are connected by an almost planar prop-2-en-1-one bridge (r.m.s. deviation = 0.022 Å), with the dihedral angles between this plane and the appended quinolinyl residues being 75.86 (7) and 38.54 (7)°. The C atom of the methoxy group is close to coplanar with its attached ring [deviation = 0.116 (2) Å]. In the crystal, a three-dimensional architecture is constructed by methyl-carbonyl C-HO interactions and - interactions between centrosymmetrically related quinolinyl residues [centroid-to-centroid separations 3.5341 (10) and 3.8719 (9) Å].
For background to the biological activities and photophysical properties of quinolines, and their utility as intermediates in organic synthesis, see: Prasath & Bhavana (2012); Joshi et al. (2011). For background to the bio-activities of quinolinyl chalcones, see: Prasath et al. (2013a). For a related structure, see: Prasath et al. (2013b).
Data collection: CrysAlis PRO (Agilent, 2013); 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: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7107 ).
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).
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.
Joshi, R. S., Mandhane, P. G., Khan, W. & Gill, C. H. (2011). J. Heterocycl. Chem. 48, 872-876.
Prasath, R. & Bhavana, P. (2012). Heteroatom Chem. 23, 525-530.
Prasath, R., Bhavana, P., Ng, S. W. & Tiekink, E. R. T. (2013a). J. Organomet. Chem. 726, 62-70.
Prasath, R., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2013b). Acta Cryst. E69, o1275.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.