Crystal and Molecular Structure of N -(Phenylthio)phthalimide
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TRUCTURE OF ORGANIC COMPOUNDS
Crystal and Molecular Structure of N-(Phenylthio)phthalimide1 Hasan Tanaka,*, Hasan Yakanb, Halil Kütükc, Nalan Türköz Karakullukçud, and Necmi Degee aDepartment
of Physics, Faculty of Arts and Sciences, Amasya University, Amasya, 05100 Turkey Chemistry Education, Faculty of Education, Ondokuz Mayis University, Atakum, Samsun, 55139 Turkey c Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayis University, Atakum, Samsun, 55139 Turkey dKaradeniz Advanced Technology Research and Application Centre, Ondokuz Mayis University, Atakum, Samsun, 55139 Turkey e Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, Atakum, Samsun, 55139 Turkey *e-mail: [email protected] b
Received February 23, 2016
Abstract—The title compound N-(Phenylthio)phthalimide has been synthesized and characterized by FT-IR, NMR, and X-ray single-crystal determination. The compound crystallizes in the triclinic sp. gr. P 1 with Z = 2. The title compound is not planar. The dihedral angle between the phthalimide and phenyl ring systems is 77.41(8)°. The crystal structure is stabilized by intermolecular π⋅⋅⋅π and C–H⋅⋅⋅π interactions. DOI: 10.1134/S1063774518030306
INTRODUCTION Phthalimides have received much attention due to their analgesic, antifungal, antibacterial, anxiolytic, antitumor, and anti-HIV activities [1]. Phthalimide derivatives have a wide range of biological activities such as antibacterial [2], antimicrobial [3], antiinflammatory [4], antioxidant, antiproliferative [5], analgesic [6], acetylcholinesterase inhibitors [7], and inhibitor of human neuronal nitric oxide synthase [8]. On the industrial scale, they are acting like bleaching detergents, anion exchange resins, antidepressants, heat resistant polymers, and flame-retardants [9]. NSubstituted phthalimides are also used in the synthesis of pesticides, mainly insecticides, herbicides and fungicides [10]. In order to investigate new organic compounds with biological activities, our group has synthesized a novel serial of derivatives of phthalimide. During this study, we have obtained the crystal structure of the title compound. In this paper, we present the crystal structural analysis of N-(Phenylthio)phthalimide.
Bruker AC 200 MHz spectrometers using TMS as internal standard. The spectra were recorded in CDCl3 (d1-chloroform) solutions and 5 mm NMR tubes were used. FT-IR: 3065–3035 cm−1 (CH), 1736–1709 cm−1 (C=O), 739 cm−1 (C–S). 1H-NMR (200 MHz, CDCl3, in ppm): δ 7.85–7.90 (m, 2H; H2, H5), 7.71–7.74 (m, 2H; H3, H4), 7.53–7.58 (dd, 2H; H10, H14), 7.28–7.30 (dd, 2H; H11, H13), 7.23–7.25 (m, 1H; H12). 13C-NMR (50 MHz, CDCl3, in ppm): δ 167.7 (C7, C8), 134.7 (C1, C6), 134.6 (C9), 131.4 (C3, C4), 131.3 (C11, C13), 130.9 (C2, C5), 128.3 (C12), 125.0 (C10, C14). X-ray Diffraction Study. The collections of the data for the title crystal were performed on a STOE IPDS II diffractometer at 296 K, using graphite-monochromated MoKα (λ = 0.71073 Å). The structure was solved by direct methods using SHELXS 97 [12]. All n
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