Crystal structure of (2E)-2-[1-(4-bromophenyl)-3-(1H-imidazol-1-yl) propylidene]-N-(2,4-dichlorophenyl)hydrazinecarboxamide, C 19 H 16 BrCl 2 N 5 O Reem I. Al-Wabli I , Mohamed I. Attia *, I, II , Hazem A. Ghabbour I , Nahed N. E. El-Sayed III, IV and Hoong-Kun Fun I, V I Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riaydh 11451, Saudi Arabia II Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, 12622, Dokki, Giza, Egypt III Department of Chemistry, College of Science, King Saud University, Female Campus, Riyadh 11451, Saudi Arabia IV National Organization for Drug Control and Research, Giza 35521, Egypt V X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 Penang, Malaysia Received January 18, 2015, accepted June 04, 2015, available online June 09, 2015, CCDC no. 1267/4328 Abstract C 19 H 16 BrCl 2 N 5 O, triclinic, P1 (no. 2), a = 7.4661(3) Å, b = 10.9874(4) Å, c = 12.8619(5) Å, a = 109.979(3)°, b = 92.053(3)°, g = 95.677(3)°, V = 984.0 Å 3 , Z = 2, R gt (F) = 0.0653, wR ref (F 2 ) = 0.1906, T = 296 K. Source of material A solution of N-(2,4-dichlorophenyl)hydrazinecarboxamide [2] (2.2 g, 10 mmol), 1-(4-bromophenyl)-3-(1H-imidazol-1-yl)- propan-1-one [3] (2.79 g, 10 mmol) and few drops of glacial ace- tic acid in ethanol (15 mL) was stirred at ambient temperature for 18 h. The reaction mixture was evaporated under reduced pres- sure and the residue was crystallized from ethanol to give 2.84 g (59%) of the title compound as colourless crystals which were suitable for single crystal x-ray analysis. m.p. 494-496 K. Discussion Epilepsy is one of the most common disorders of the brain, affect- ing more than 50 million individuals worldwide [4]. However, only about 70% of patients suffering from epilepsy are ade- quately controlled by the currently available anti-epileptic drugs (AEDs) [5]. Therefore, the search for more effective and safer new AEDs should have a considerable attention. The title com- pound showed 16 and 50% seizure inhibition in animal model mice using maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) convulsive screens, respectively, at a dose level of 520 mmol/kg [6]. X-ray crystallography is a decisive analytical tool which can confirm the configuration of the title compound. Fortunately, we have succeeded to get single crystals of the title compound which were suitable for x-ray crystallogra- phy. The crystal structure of the target compound contains one molecule in the asymmetric unit. The two six-membered rings (C1-C6 and C14-C19) are nearly planner. The dihedral angle be- tween the two six-membered rings is 8.7(10)°. The dihedral an- gles between the six-membered rings (C1-C6 and C14-C19) and the imidazole ring (N1/N2/C10-C12) are 44.62(13)° and 48.82(13)°, respectively. The packing in the crystal structure is stabilized by two inter-molecular hydrogen bonds, of which N1 works as hydrogen bond acceptor and N4 and C4 work as hydro- gen bond donors. The distance of the interactions between N46–H1N4×××N1 is 2.12(6) Å and C8–H8A×××N1 is 2.53(1) Å and the angles are 165.00(6)° and 141.00(1)°, respectively. Z. Kristallogr. NCS 230 (2015) 219-220 / DOI 10.1515/ncrs-2014-9078 219 © 2015 Walter de Gruyter GmbH, Berlin/Munich/Boston Crystal: colourless plates, size 0.06´0.32´0.34 mm Wavelength: Cu K a radiation (1.54178 Å) m: 55.22 cm -1 Diffractometer, scan mode: Bruker APEX-II CCD, j and w 2q max : 139.36° N(hkl) measured , N(hkl) unique : 12681, 3565 Criterion for I obs , N(hkl) gt : I obs >2 s(I obs ), 2032 N(param) refined : 262 Programs: SHELX [1] Table 1. Data collection and handling. _____________ * Correspondence author (e-mail: mattia@ksu.edu.sa) H(1A) 2i -0.0852 0.6360 0.4412 0.072 H(2A) 2i -0.3586 0.5156 0.4346 0.072 H(4A) 2i -0.1839 0.2122 0.2017 0.076 H(5A) 2i 0.0863 0.3349 0.2099 0.074 H(8A) 2i 0.3816 0.7223 0.4400 0.063 H(8B) 2i 0.1964 0.7023 0.4894 0.063 H(9A) 2i 0.2496 0.8309 0.3336 0.069 H(9B) 2i 0.0607 0.8064 0.3774 0.069 H(10A) 2i 0.1244 0.9068 0.6242 0.084 H(11A) 2i 0.2434 1.1294 0.7331 0.076 H(12A) 2i 0.3621 1.0683 0.4289 0.078 H(15A) 2i 0.8326 0.4468 0.0186 0.065 H(16A) 2i 0.9820 0.2830 -0.0914 0.069 H(18A) 2i 0.5473 0.0247 -0.1190 0.069 H(1N4) 2i 0.502(8) 0.685(6) 0.299(5) 0.06(2) H(1N5) 2i 0.425(8) 0.404(5) 0.104(4) 0.04(2) Table 2. Atomic coordinates and displacement parameters (in Å 2 ). Atom Site x y z U iso Unauthenticated Download Date | 9/15/15 10:20 AM