X-ray and DFT calculated structures of 2-(1 H -imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N -phenylthiosemicarbazone and 2
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TRUCTURE OF ORGANIC COMPOUNDS
Xray and DFT Calculated Structures of 2(1HImidazol1yl)1(2naphthyl)ethan1one Nphenylthiosemicarbazone and 2(1HImidazol1yl)1(2naphthyl)ethan1one N(4chlorophenyl)thiosemicarbazone1 Z. S. Sahina, E. Septioglub, U. Calisb, and S. Isika a
Sinop University, Faculty of Engineering and Architecture, Department of Energy Systems Engineering, Sinop, 57000 Turkey b Hacettepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara, 06100 Turkey email: [email protected] Received September 19, 2013
Abstract—Crystal and molecular structures of two new compounds 2(1Himidazol1yl)1(2naph thyl)ethan1one Nphenylthiosemicarbazone, C22H19N5S, (I) and 2(1Himidazol1yl)1(2naph thyl)ethan1one N(4chlorophenyl)thiosemicarbazone, C22H18ClN5S, (II) have been determined by sin glecrystal Xray diffraction. Molecular geometries from Xray experiment of I and II have been compared with those calculated using the Density Functional Theory (DFT) with B3LYP/631G(d,p) basis set. Both compounds crystallize in the monoclinic space group P21/c with Z = 4: a = 13.2880(5), 14.2648(3) Å, b = 9.4122(2), 9.3892(3) Å, c = 15.6341(6), 15.6268(4) Å, β = 101.779(3)°, 104.926(2)°, for I and II, respec tively. An extensive twodimensional network of N–H⋅⋅⋅N hydrogen bonds and πring interactions are responsible for crystal stabilization in both structures. DOI: 10.1134/S1063774514070177 1
INTRODUCTION
EXPERIMENTAL
Thiosemicarbazones are derivatives of carbonyl compounds, exhibiting a wide range of biological activities. Therefore, much attention has been devoted to the synthesis of new thiosemicarbazones [1–3]. Research on the reactions of thiosemicarbazones with transition metals has increased steadily for many years due to the variety of their biological activities, such as antitumor, antiviral and fungicidal [4, 5]. The effect of thiosemicarbazones against the human immunodefi ciency virus (HIV) has also been reported [6] Besides, recently, the anticonvulsant activities of semicarba zone derivatives were reported [7, 8].
XRay diffraction analysis. The parameters for data collection and structure refinement of structures I and II are listed in Table 1. The structures were solved by directmethods. All nonhydrogen atoms were refined with anisotropic parameters. H atoms bonded to C and N atoms were placed in calculated positions (C–H = 0.93–0.97, N–H = 0.86 Å) and treated using a riding model with UH = 1.2 U value of the parent atom for CH, NH and CH2. Crystallographic data have been deposited with Cambridge Crystallographic Data Centre, CCDC reference numbers 831874 (I) and 831875 (II). These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing [email protected], or by con tacting The Cambridge Crystal lographic Data Cen tre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
In view of the importance of thiosemicarbazones, two new thiosemicarbazone, (I and II), have been pre pared to evaluate the
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