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A facile approach for the synthesis of indenoimidazole derivatives and their supramolecular study

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Abstract

The structures of the title Indeno-imidazole compounds, have been determined by FTIR, NMR, mass and single crystal X-ray diffraction. 3a,8a-Dihydroxy-1-phenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione (1) crystallizes in the monoclinic, space group P2 1/c with a = 12.0913(7) Å, b = 5.7204(3) Å, c = 19.8168(11) Å, α= 90.00 ∘, β= 103.6650(10) ∘, γ= 90.00 ∘, V = 1331.87(13) Å 3, Z = 4; while 3a,8a-Dihydroxy-1-phenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazol-8-one (2) crystallizes in the monoclinic, space group P2 1/c with a = 11.0101(5) Å, b = 6.8421(3) Å, c = 21.1243(9) Å, α= 90.00 ∘, β= 110.771(2) ∘, γ= 90.00 ∘, V = 1487.91(11) Å 3, Z = 4. Solid-state crystal structures of compounds 1 and 2 are presented here in terms of crystal engineering and supramolecular chemistry. Replacement of oxygen atom of compound 1 by sulfur atom in compound 2 forced compound 2 to hold water molecules and formed the hydrated form.

Indaneimidazoles have been synthesized. The structures of 1:1 adducts were assigned based on spectral analysis and X-ray analysis. Molecular structures contain two different types of cyclic amide groups as lactam and thiolactam. Both title molecules form centrosymmetric dimers by strong hydrogen bonding in 1 while through sulfurhydrogen interaction in 2.

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References

  1. Roberts L R, Bryans J, Conlon K, McMurray G, Stobie A and Whitlock G A 2008 Bioorg. Med. Chem. Lett. 18 6437

    Article  CAS  Google Scholar 

  2. Sarra J D and Stephani R A 2000 Med. Chem. Res. 10 81

    CAS  Google Scholar 

  3. Chen W, Yang L -J, Li Y, Wang X -Q, Wang S -J, Wan W -C, Zhang H -B and Yang X -D 2013 Lett. Drug Des. Discov. 10 561

    Article  CAS  Google Scholar 

  4. Sarkarzadeh H, Miri R, Firuzi O, Amini M, Razzaghi-Asl N, Edraki N and Shafiee A 2013 Arch. Pharm. Res. 36 436

    Article  CAS  Google Scholar 

  5. Devi T U, Priya S, Selvanayagam S, Ravikumar K and Anitha K 2012 Spectrochim. Acta Mol. Biomol. Spectros. 97 1063

    Article  Google Scholar 

  6. Shapiro R and Chatterjie N 1970 J. Org. Chem. 35 447

    Article  CAS  Google Scholar 

  7. Hossaini Z, Seyfi S, Rostami-Charati F and Ghambarian M 2013 Comb. Chem. High T. Scr. 16 788

    CAS  Google Scholar 

  8. Chatterjie N, Sinha B and Alexander G J 1983 Res. Commun. Chem. Pathol. Pharmacol. 39 333

    CAS  Google Scholar 

  9. Ghalib R M, Hashim R, Mehdi S H, Quah C K and Fun H -K 2011 Acta Cryst. E 67 o1525

    Article  CAS  Google Scholar 

  10. Hasenknopf B, Lehn J -M, Kneisel B O, Baum G and Fenske D 1996 Angew Chem. Int. Ed. 35 1838

    Article  CAS  Google Scholar 

  11. Day A I 2002 Angew. Chem. Int. Ed. 41 275

    Article  CAS  Google Scholar 

  12. Bravo J A 1998 Eur. J. Org. Chem. 1998 2565

    Article  Google Scholar 

  13. Anderson S, Anderson H L, Bashall A, McPartlin M and Sanders J K M 1995 Angew Chem. Int. Ed. 34 1096

    Article  CAS  Google Scholar 

  14. Freeman W A 1984 Acta Cryst. Sect. B 40 382

    Article  Google Scholar 

  15. Schmitt J -L, Stadler A -M, Kyritsakas N and Lehn J -M 2003 Helv. Chim. Acta 86 1598

    Article  CAS  Google Scholar 

  16. Lehn J -M 1993 Science 260 1762

    Article  CAS  Google Scholar 

  17. Lehn J -M., 1995 In Supramolecular Chemistry (Weinheim: Wiley-VCH Verlag GmbH)

  18. Gennady V, Oshovsky David N R and Willem V 2007 Angew. Chem. Int. Ed. 46 2366

    Article  Google Scholar 

  19. Alshahateet S F, Bishop R, Craig D C and Scudder M L 2011 Cryst. Growth Des. 11 4474

    Article  CAS  Google Scholar 

  20. Ghalib R M, Hashim R, Alshahateet S F, Mehdi S H, Sulaiman O, Chan K -L, Murugaiyah V and Jawad A 2012 J. Chem. Crystallogr. 42 783

    Article  CAS  Google Scholar 

  21. MacNicol D D and Downing G R., 1996 In Symmetry in the evolution of host design, in Comprehensive Supramolecular Chemistry, Vol. 6 Solid-state Supramolecular Chemistry: Crystal Engineering D MacNicol, F Toda and R Bishop (Eds.) (Oxford: Pergamon Press) Ch. 14 pp. 421–464

  22. Ghalib R M, Hashim R, Alshahateet S F, Mehdi S H, Sulaiman O, Murugaiyah V and Aruldass C A 2011 J. Mol. Struct. 1005 152

    Article  CAS  Google Scholar 

  23. Alshahateet S F, Al-Zereini W A and Alghezawi N M 2011 J. Chem. Crystallogr. 41 1807

    Article  CAS  Google Scholar 

  24. Kooli F, Hian P C, Weirong Q, Alshahateet S F and Chen F 2006 J. Porous Mat. 13 319

    Article  CAS  Google Scholar 

  25. Alshahateet S F, Bishop R, Craig D C and Scudder M L 2003 CrystEngComm 3 417

    Article  Google Scholar 

  26. Alshahateet S F, Bishop R, Craig D C and Scudder M L 2010 Cryst. Growth Des. 10 1842

    Article  CAS  Google Scholar 

  27. Alshahateet S F, Bishop R, Scudder M L, Hu C Y, Lau E H E, Kooli F, Judeh Z M A, Chow P S and Tan R B H 2005 CrystEngComm 7 139

    Article  CAS  Google Scholar 

  28. Kooli F, Mainhui L, Alshahateet S F, Chen F and Yinghuai Z 2006 J. Phys. Chem. Solids 67 926

    Article  CAS  Google Scholar 

  29. Alshahateet S F, Bishop R, Craig D C, Kooli F and Scudder M L 2008 CrystEngComm 10 297

    Article  CAS  Google Scholar 

  30. Alshahateet S F, Ong T T, Bishop R, Kooli and Messali M 2006 Cryst. Growth Des. 6 1676

    Article  CAS  Google Scholar 

  31. Alshahateet S F, Bishop R, Craig D C, Scudder M L and Ung A T 2001 Struct. Chem. 12 251

    Article  CAS  Google Scholar 

  32. Alshahateet S F, Bhadbhade M M, Bishop R and Scudder M L 2015 CrystEngComm 17 877

    Article  CAS  Google Scholar 

  33. Alshahateet S F, Bhadbhade M M, Bishop R, Craig D C and Scudder M L 2015 CrystEngComm 17 9111

    Article  CAS  Google Scholar 

  34. Alshahateet S F 2015 Mol. Cryst. Liq. Cryst. 607 169

    Article  CAS  Google Scholar 

  35. SMART and SAINT 1996 Software Reference Manuals Version 4.0 (Siemens Energy and Automation, Inc., Analytical Instrumentation: Madison, WI)

  36. Sheldrick G M 1996 In SADABS (Germany: University of Göttingen)

    Google Scholar 

  37. Sheldrick G M 2008 SHELXS and SHELXL Acta Crystallogr. A 64 112

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Authors would like to acknowledge University of Jeddah, KSA and Universiti Sains Malaysia (USM) for the research facilities.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences and Arts–Khulais, University of Jeddah, P.O. Box-355, Postal Code-21921, Jeddah, Kingdom of Saudi Arabia

    RAZA MURAD GHALIB

  2. Department of Chemistry, S P G College, University of Lucknow, Lucknow, Uttar Pradesh, 226 020, India

    SAYED HASAN MEHDI

  3. School of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia

    RAZA MURAD GHALIB, ROKIAH HASHIM & OTHMAN SULAIMAN

  4. Department of Chemistry, Mutah University, P.O. BOX 7, Mutah, 61710, Karak, Jordan

    SOLHE F ALSHAHATEET

Authors
  1. RAZA MURAD GHALIB
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  2. SAYED HASAN MEHDI
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  3. ROKIAH HASHIM
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  4. SOLHE F ALSHAHATEET
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Correspondence to RAZA MURAD GHALIB.

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Supplementary Information (SI)

Scanned copies of 1H and 13C spectra of 1 and 2 are given in electronic Supporting Information available at www.ias.ac.in/chemsci. CCDC-1042090 and 1042091 contain the supplementary crystallographic data for 1 and 2. This data can be obtained free of charge at http://www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: + 44(0)1223-336033; email: deposit@ccdc.cam.ac.uk].

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GHALIB, R.M., MEHDI, S.H., HASHIM, R. et al. A facile approach for the synthesis of indenoimidazole derivatives and their supramolecular study. J Chem Sci 128, 1841–1847 (2016). https://doi.org/10.1007/s12039-016-1181-2

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  • DOI: https://doi.org/10.1007/s12039-016-1181-2

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