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2005 | 3 | 4 | 780-791
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The crystal structure of 1-(4-chlorophenyl)-3-(4-methylbenzoyl)thiourea

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1-(4-Chlorophenyl)-3-(4-methylbenzoyl)thiourea was synthesized and characterized by IR,1H and 13C NMR, mass spectroscopy and the elemental analysis. The crystal structure was confirmed from single crystal X-ray diffraction data. It crystallizes in the monoclinic space group P21/c with unit cell dimensions a=12.038(3), b=6.330(6), c=18.912(5) Å and β=100.32(3)°. There is a strong intramolecular hydrogen bond of the type N−H...O, with distance N1...O1=2.659(3) Å. The structure is composed of dimers related by inversion centers. The dimers are formed by intermolecular interactions of the type N−H...S with N...S separation of 3.440(2) Å. The mass fragmentation pattern has also been discussed.

Opis fizyczny
  • Department of Chemistry, Quaid-I-Azam University, 45320, Islamabad, Pakistan,
  • Department of Chemistry, University of Calgary, 2500 University Drive, N.W., T2N 1N4, Calgary, Alberta, Canada
  • [1] R.S. Zeng, J.P. Zou, S.J. Zhi, J. Chen and Q. Shen: “Novel Synthesis of 1-Aroyl-3-aryl-4-substitutedImidazole-2-thiones”, Organic. Lett., Vol. 61, (2003), pp. 1657–1659.[Crossref]
  • [2] M. D'hooghe, A. Waterinckx and N. De Kimpe: “A Novel Entry toward 2-Imino-1,3-thiazolidines and 2-Imino-1,3-thiazolines by Ring Transformation of 2-(Thiocyanomethyl)aziridines”, J. Org. Chem., Vol. 70, (2005), pp. 227–232.[Crossref]
  • [3] V.K. Jain and J.T. Rao: “Pyrimidines-2-thiones/ols and 1-acetyl pyrimidines-2-thiones/ols”, J. Institution Chem. (India), Vol. 75, (2003), pp. 24–26.
  • [4] R. Lakhan and B.J. Ral: “Synthesis of Some New 3–4 2′-Benzothiazolyl)-4(3H)-quinazolinones as Antifungal Agents”, J. Chem. Eng. Data, Vol. 31, (1986), pp. 501–502.[Crossref]
  • [5] J. Lee, J. Lee, M. Kang, M. Shin, J.M. Kim, S.U. Kang, J.O. Lim, H.K. Choi, Y.G. Suh, H.G. Park, U. Oh, H.D. Kim, Y.H. Park, H.J. Ha, Y.H. Kim, A. Toth, Y. Wang, R. Tran, L.V. Pearce, D.J. Lundberg and P.M. Blumberg: “N-(3-Acyloxy-2-benzylpropyl)-N′-[4-(methylsulfonylamino)benzyl]thiourea Analogues: Novel Potent and High Affinity Antagonists and Partial Antagonists of the Vanilloid Receptor”, J. Med. Chem., Vol. 46, (2003), pp. 3116–3126.[Crossref]
  • [6] L. Nie, Z. Li, J. Han, X. Zhang, R. Yang, W.X. Liu, F.Y. Wu, J.W. Xie, Y.F. Zhao and Y.B. Jiang: “Development of N-Benzamidothioureas as a New Generation of Thiourea-Based Receptors for Anion Recognition and Sensing”, J. Org. Chem., Vol. 69, (2004) pp. 6449–6454.[Crossref]
  • [7] H. Park, J. Choi, S. Choi, M. Park, J. Lee, J.Y. Suh, H. Cho, H.U. Oh, J. Lee, S.U. Kang, J. Lee, H.D. Kim, Y.H. Park, Y.S. Jeong, J.K. Choi and J.S. Jew: “N-4-Substitued-benzyl-N′-ter-butylbenzyl thioureas as vanilloid receptors ligands: investigation on the role of methanesulfonamido group in antagonistic activity”, Bioorg Med. Chem. Lett., Vol. 14, (2004), pp. 787–791.[Crossref]
  • [8] O.F. Huebner, J.L. Marsh, R.H. Mizzoni, R.P. Mull, D.C. Schroeder, H.A. Troxell and C.R. Scholz: “A New Class of Antitubercular Compounds”, J. Am. Chem. Soc., Vol. 75, (1953), pp. 2274–2275.[Crossref]
  • [9] A.C. Glasser and R.M. Doughty: “Heterocyclic Thioureas. II. Antitubercular activity of diheterocyclic thioureas”, J. Pharm. Sci., Vol. 53, (1964), pp. 40–42.[Crossref]
  • [10] Y. Xu, W. Hua, X. Liu, and D. Zhu: “Synthesis and Biological Activity of S-Alkyl (or aralkyl)-1-alkyl-3-[4-(benzothiazole-2-mercapto)phenylisothioureas”, Chinese J. Org. Chem., Vol. 24, (2004), pp. 1217–1222.
  • [11] W. Zheng, S.R. Yates, S.K. Papiernik, and M. Guo: “Transformation of herbicide Propachlor by an agrochemical thiourea”, Environ. Sci. Technol., Vol. 38, (2004), pp. 6855–6860.[Crossref]
  • [12] F. Libe and U.C. Philip: “Miscellaneous structures of New Herbicides”, Chem. Plant Prot., Vol. 10, (1994), pp. 189–216 and 65 references therein.
  • [13] S. Xue, L. Duan, S. Ke and L. Jia: “Synthesis, Crystal structure and herbicidal activity of 1-benzoyl-3-(4,6-disubstituted pyrimidine-2yl)-thiourea derivatives”, Chemistry Magazine, Vol. 5, (2003), pp. 67–70.
  • [14] C. Ru, Y. Wang, J. Li, D. Ma, F. Gong, Y. Liu and P. Lu: “Synthesis and physiological activity of acyl thiourea compounds”, Yingyong Huaxue, Vol. 11, (1994), pp. 82–85.
  • [15] W. Wasiak: “Chemically bounded chelates as selective coplexing sorbents for gas chromatography III. Silica chemically modified by N-benzoyl thiourea groups”, J. Chromatogr. A, Vol. 690, (1995), pp. 93–102.[Crossref]
  • [16] K.R. Koch, C. Sacht, T. Grimmbacher and S. Bourne: “New ligands for platinum group metals: deceptively simple coordination chemistry of N-acyl-N′-alkyl and N, N′-dialkyl thioureas”, S. Afr. J. Chem. Vol. 48, (1995), pp. 71–77.
  • [17] V. Carcu, M. Negoiu, T. Rosu and S. Serban: “Synthesis, characterization of complexes of N-benzoyl-N′-2-nitro-4-methoxy phenylthiourrea with Cu, Ni, Pt, Pd, Cd and Hg”, J. Therm. Anal. & Cal., Vol. 126, (2000), pp. 935–945.[Crossref]
  • [18] G. Avsar, H. Arsalan, H. J. Haupt and N. Kulcu: “Crystal structure of cis-bis(N,N-dimethyl-N′-benzoylthioureato) palladium (II)”, Turk. J. Chem., Vol. 27, (2003), pp. 281–285.
  • [19] M. Schuster: “Selective complexing agents for the trace enrichment of platinum metals”, Fresenius J. Anal. Chem., Vol. 342, (1992), pp. 791–794.[Crossref]
  • [20] F.A. French, E.J. Blanz, J.R.D. Amaral and D.A. French: “Carcinostatic activity of thiosemicarbazones of formyl heteroaromatic compounds VI.1-Formylisoquinoline derivatives bearing additional ring substitutents, with notes on mechanism of action”, J. Med. Chem., Vol. 13, (1970), pp. 1117–1124.[Crossref]
  • [21] I.B. Douglas and F.B. Dains: “Some derivatives and furoyl isothiocyanates and their use in synthesizing heterocyclic compounds”, J. Amer. Chem. Soc., Vol. 56, (1934), pp. 719–721.[Crossref]
  • [22] Z-M. Jin, W. Zhao and Z. Jin: “X-ray powder diffraction analysis of a non- linear optical material o-chlorophenylbenzoyl thionrea”, Powder Diff., Vol. 12, (1997), pp. 47–48.
  • [23] D.C. Zhang, Y.Q. Zhang, Y. Cao and B. Zao: “1-Benzoyl-3-(4-nitrophenyl) thiourea”, Acta Crystallogr. C, Vol. 52, (1996), pp. 1716–718.[Crossref]
  • [24] F.H. Allen and W.D.S. Motherwell: Acta Crystallogr. B, Vol. 58, (2002), pp. 407–422.[Crossref]
  • [25] J. Bernstein, M.C. Etter and L. Leiserowitz, In: H.-B. Bürgi and J.D. Dunitz (Eds.): Structure Correlation, Vol. 2, VCH Publishers, New York, 1994, pp. 431–507.
  • [26] Z. Otwinowski and W. Minor: “Processing of X-ray Diffraction Data Collected in Oscillation Mode”, Methods in Enzymology, Vol. 276, (1997); C.W. Carter, Jr. and R.M. Sweet (Eds.): Macromolecular Crystallograpy, part A, Academic Press, pp. 307–326.
  • [27] R. Hooft: COLLECT: Users Manual, Nonius B.V., Delft. The Netherlands, 1998.
  • [28] A. Altomare, M. Cascarano, C. Giacovazzo and A. Guagliardi: “Completion and Refinement of Crystal Structures with SIR92”, J. Appl. Cryst., Vol. 26, (1993), pp. 343–350.[Crossref]
  • [29] P.T. Beurskens, G. Admiraal, G. Beurskens, W.P. Bosman, R. de Gelder, R. Israel and J.M.M. Smits: “The DIRDIF-94 program system, Technical Report of the Crystallography Laboratory”, University of Nijmegen, The Netherlands, 1994.
  • [30] G.M. Sheldrick: SHELXL97, A Program for Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
  • [31] C.K. Johnson: ORTEPH, Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA, 1976.
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