1-{6-Chloro-2-[(2-chloro-6-methyl- quinolin-3-yl)methoxy]-4-phenyl- quinolin-3-yl}ethanone F. Nawaz Khan, a Venkatesha R. Hathwar, b Rajesh Kumar, a Atul Kumar Kushwaha a and Mehmet Akkurt c * a Organic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, b Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and c Department of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey Correspondence e-mail: akkurt@erciyes.edu.tr Received 8 June 2010; accepted 13 June 2010 Key indicators: single-crystal X-ray study; T = 295 K; mean (C–C) = 0.003 A ˚ ; R factor = 0.038; wR factor = 0.103; data-to-parameter ratio = 14.5. In the title compound, C 28 H 20 Cl 2 N 2 O 2 , the 2-chloroquinoline and 6-chloroquinoline ring systems are twisted slightly, making a dihedral angle of 4.05 (3)  . The dihedral angle between the 2-quinoline ring system and the phenyl ring attached to it is 74.43 (5)  . In the crystal structure, a pair of intermolecular C—HO hydrogen bonds connect the mol- ecules, forming centrosymmetric dimers with R 2 2 (16) motifs. The dimers are further consolidated by a C—H inter- action and a – stacking interaction with a centroid–centroid distance of 3.6562 (10) A ˚ . Related literature For related structures, see: Khan, Roopan, Hathwar & Akkurt (2010); Khan, Roopan, Kumar et al. (2010); Roopan & Khan (2009). For the biological acivity of 2-quinolone derivatives, see: Ukita & Mizuno (1960); Jayashree et al. (2010); Joseph et al. (2002); Xiao et al. (2001). For hydrogen-bond motifs, see: Bernstein et al. (1995). Experimental Crystal data C 28 H 20 Cl 2 N 2 O 2 M r = 487.36 Triclinic, P 1 a = 8.0552 (2) A ˚ b = 12.4499 (5) A ˚ c = 13.3718 (5) A ˚  = 67.555 (4)   = 80.183 (3)   = 77.273 (3)  V = 1203.40 (8) A ˚ 3 Z =2 Mo K radiation  = 0.30 mm 1 T = 295 K 0.24  0.18  0.17 mm Data collection Oxford Xcalibur Eos (Nova) CCD detector diffractometer Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009) T min = 0.912, T max = 0.951 23521 measured reflections 4468 independent reflections 3013 reflections with I >2(I) R int = 0.034 Refinement R[F 2 >2(F 2 )] = 0.038 wR(F 2 ) = 0.103 S = 1.05 4468 reflections 309 parameters H-atom parameters constrained Á max = 0.18 e A ˚ 3 Á min = 0.20 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ ,  ). Cg4 is the centroid of the C14–C19 ring. D—HA D—H HA DA D—HA C3—H3O1 0.93 2.39 2.735 (2) 101 C24—H24O2 i 0.93 2.51 3.392 (3) 157 C10—H10ACg4 ii 0.97 2.67 3.4430 (18) 137 Symmetry codes: (i) x; y þ 1; z; (ii) x; y þ 2; z. Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST (Nardelli, 1983) and PLATON (Spek, 2009). We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA– DST program at IISc. We thank Professor T. N. Guru Row, IISc, Bangalore for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2563). References Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Jayashree, B. S., Thomas, S. & Nayak, Y. (2010). Med. Chem. Res. 19, 193–209. Joseph, B., Darro, F., Behard, A., Lesur, B., Collignon, F., Decaestecker, C., Frydman, A., Guillaumet, G. & Kiss, R. (2002). J. Med. Chem. 45, 2543– 2555. organic compounds Acta Cryst. (2010). E66, o1693–o1694 doi:10.1107/S1600536810022701 Khan et al. o1693 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368