1-[4-(4-Chlorophenyl)piperazin-1-yl]-3- (6-oxo-3,4-diphenyl-1,6-dihydro- pyridazin-1-yl)propan-1-one Abdullah Aydın, a * Mehmet Akkurt, b Deniz S. Dog ˘ruer c and Orhan Bu ¨yu ¨kgu ¨ngo ¨r d a Department of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, b Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, c Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey, and d Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey Correspondence e-mail: aaydin@kastamonu.edu.tr Received 26 July 2012; accepted 10 August 2012 Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.003 A ˚ ; R factor = 0.041; wR factor = 0.111; data-to-parameter ratio = 15.2. In the title compound, C 29 H 27 ClN 4 O 2 , the six-membered ring of the pyridazine group is nearly planar [maximum deviation = 0.062 (2) A ˚ ] and its mean plane makes dihedral angles of 43.05 (9), 44.71 (10) and 72.57 (9) , respectively, with the two phenyl and benzene rings. The piperazine ring has a chair conformation and its mean plane is almost perpendicular to the attached benzene ring, with a dihedral angle of 83.20 (16) . In the crystal, molecules are linked via two pairs of C—HO interactions, which result in the formation of chains propa- gating along [10 1]. Neighbouring chains are linked via C— H interactions. Related literature For the synthesis and biological activity of the title compound, see; Dog ˘ ruer et al. (2007). For related structures, see: Aydın et al. (2008); Girisha et al. (2008). For puckering parameters, see: Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987). Experimental Crystal data C 29 H 27 ClN 4 O 2 M r = 499.00 Triclinic, P 1 a = 10.7929 (10) A ˚ b = 10.8527 (10) A ˚ c = 12.7815 (13) A ˚ = 97.745 (8) = 104.041 (7) = 115.635 (7) V = 1259.3 (2) A ˚ 3 Z =2 Mo K radiation = 0.19 mm 1 T = 296 K 0.66 0.53 0.35 mm Data collection Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T min = 0.784, T max = 0.948 15922 measured reflections 4945 independent reflections 3837 reflections with I >2(I) R int = 0.059 Refinement R[F 2 >2(F 2 )] = 0.041 wR(F 2 ) = 0.111 S = 1.05 4945 reflections 326 parameters H-atom parameters constrained Á max = 0.29 e A ˚ 3 Á min = 0.37 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). Cg1 and Cg4 are the centroids of the N1/N2/C1–C4 and C11–C16 rings, respectively. D—HA D—H HA DA D—HA C12—H12O1 i 0.93 2.44 3.323 (2) 158 C25—H25O2 ii 0.93 2.53 3.289 (3) 139 C10—H10Cg1 iii 0.93 2.88 3.431 (2) 119 C29—H29Cg4 iv 0.93 2.86 3.762 (2) 165 Symmetry codes: (i) x þ 2; y þ 2; z þ 2; (ii) x þ 1; y þ 2; z þ 1; (iii) x þ 1; y þ 1; z þ 2; (iv) x; y; z 1. Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X- AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al. , 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999). The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2489). References 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. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Aydın, A., Dog ˘ruer, D. S., Akkurt, M. & Bu ¨yu ¨ kgu ¨ ngo ¨r, O. (2008). Acta Cryst. E64, o1030. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. Dog ˘ ruer, D. S., U ¨ nlu ¨ , S., Ku ¨peli, E., Banoglu, E. & Sahin, M. F. (2007). Turk. J. Pharm. Sci. 4, 57–70. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Girisha, H. R., Naveen, S., Vinaya, K., Sridhar, M. A., Shashidhara Prasad, J. & Rangappa, K. S. (2008). Acta Cryst. E64, o358. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. organic compounds o2720 Aydın et al. doi:10.1107/S160053681203543X Acta Cryst. (2012). E68, o2720 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368