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Structures of Two Rotamers of the HCl Salt of 4-Methyl-2-[(1E)-[2-(quinolin-4-yl)hydrazin-1-ylidene]methyl]phenol: Different Supramolecular Arrays

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Abstract

Crystallography reveals the rotomer in the salt isolated from EtOH solution has an anti disposition of the OH and imine-NH hydrogen atoms while that from EtOCH2CH2OH solution has a syn disposition. Both molecules have an E configuration about the C=N bond and are essentially planar (dihedral angles between aromatic groups = 2.4 (3)° and 6.42 (9)°, respectively). The anti-rotomer crystallizes in the monoclinic space group P21/n with a = 10.8795 (10) Å, b = 10.7730 (11) Å, c = 13.1257 (7) Å, λ = 104.806 (5)°, and Z = 4. The syn-rotomer crystallizes in the monoclinic space group C2/c with a = 14.4610 (5) Å, b = 11.3073 (5) Å, c = 17.8849 (7) Å, β = 91.904 (2)°, and Z = 8.

Graphical Abstract

Planar anti- and syn-rotomers of the title compound feature intramolecular O–H···N or intermolecular O–H···Cl hydrogen bonds, respectively, and two- and three-dimensional supramolecular architectures, respectively.

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References

  1. Font M, Monge A, Ruiz I, Heras B (1997) Drug Des Discov 14:59

    Google Scholar 

  2. Nakamura T, Oka M, Aizawa K, Soda H, Fukuda M, Terashi K, Ikeda K, Mizuta Y, Noguchi Y, Kimura Y, Tsuruo T, Kohno S (1999) Biochem Biophys Res Commun 255:618

    Article  CAS  Google Scholar 

  3. Montenegro RC, Lotufo LV, de Moraes MO, Pessoa CO, Rodriques FAR, Bispo MLF, Cardoso LNF, Kaiser CR, de Souza MVN (2011) Med Chem 7:599

    Article  CAS  Google Scholar 

  4. Kaminsky D, Meltzer RI (1968) J Med Chem 11:160

    Article  CAS  Google Scholar 

  5. de Souza MVN, Pais KC, Kaiser CR, Peralta MA, Ferreira ML, Lourenco MCS (2007) Bioorg Med Chem 17:1474

    Article  Google Scholar 

  6. Candea ALP, Ferreira ML, Pais KC, Cardoso LNF, Kaiser CR, Henriques MGMO, Lourenco MCS, Bezerra FAFM, de Souza MVN (2009) Bioorg Med Chem Lett 19:6272

    Article  CAS  Google Scholar 

  7. de Souza MVN, Vasconcelos TA, Cardoso SH, Almeida MV (2006) Curr Med Chem 13:455

    Article  Google Scholar 

  8. Rustomjee R, Diacon AH, Allen J, Venter A, Reddy C, Patientia RF, Mthiyane TCP, de Marez T, Van Heeswijk R, Kerstens R, Koul A, de Beule K, Donald PR, McNeeley DF (2008) Antimicrob Agents Chemother 52:2831

    Article  CAS  Google Scholar 

  9. Ferreira ML, Gonçalves RSB, Cardoso LNF, Kaiser CR, Candéa ALP, Henriques MGMO, Lourenço MCS, Bezerra FAFM, de Souza MVN (2010) ScientificWorldJournal 10:1347–1355

    Article  CAS  Google Scholar 

  10. Musiol R, Jampilek J, Buchta V, Silva L, Halina H, Podeszwa B, Palka A, Majerz-Maniecka K, Oleksyn B, Polanski J (2006) Bioorg Med Chem 14:359

    Article  Google Scholar 

  11. Warshakoon NC, Sheville J, Bhatt RT, Ji W, Mendez-Andino JL, Meyers KM, Kim N, Wos JA, Mitchell C, Paris JL, Pinney BB, Reizes O, Hu XE (2006) Bioorg Med Chem Lett 16:5207

    Article  CAS  Google Scholar 

  12. Sloboda AE, Powell D, Poletto JF, Pickett WC, Gibbons JJ, Bell DH, Oronsky AL, Kerwar SJ (1991) J Rheumatol 18:855

    CAS  Google Scholar 

  13. Kaiser CR, Pais KC, de Souza MVN, Wardell JL, Wardell SMSV, Tiekink ERT (2009) CrystEngComm 11:1133

    Article  CAS  Google Scholar 

  14. Goncalves RSB, Kaiser CR, de Souza MVN, Wardell JL, Wardell SMSV, Howie RA (2011) Z Kristallogr 226:793

    Article  CAS  Google Scholar 

  15. Wardell JL, de Souza MVN, Wardell SMSV, Lourenço MCS (2011) J Mol Struct 990:67

    Article  CAS  Google Scholar 

  16. Wardell SMSV, Wardell JL, Skakle JMS, Tiekink ERT (2011) Z Kristallogr 226:68

    Article  CAS  Google Scholar 

  17. Goncalves RSB, Kaiser CR, Lourenco MCS, Bezerra FAFM, de Souza MVN, Wardell JL, Wardell SMSV, Henriques MGMO, Costa T (2012) Bioorg Med Chem 20:243

    Article  CAS  Google Scholar 

  18. Kaiser CR, Pais KC, de Souza MVN, Wardell JL, Wardell SMSV, Tiekink ERT (2009) CrystEngComm 11:1133

    Article  CAS  Google Scholar 

  19. Tiekink ET, Wardell SMSV, Wardell JL, Ferreira ML, de Souza MVN, Kaiser CR (2012) Acta Crystallogr E68:o1850

    Google Scholar 

  20. Wardell SMSV, Tiekink ERT, Wardell JL, Ferreira ML, de Souza MVN (2012) Acta Crystallogr E68:o1232

    Google Scholar 

  21. Sheldrick GM (2007) SADABS. University of Göttingen, Göttingen

    Google Scholar 

  22. Hooft RWW (1998) COLLECT data collection software. Nonius B.V, Delft

    Google Scholar 

  23. Otwinowski Z, Minor W (1997) In: Carter CW Jr, Sweet RM (eds) Methods in enzymology, vol 276: macromolecular crystallography, part A. Academic Press, New York, pp 307–326

    Chapter  Google Scholar 

  24. Sheldrick GM (2008) Acta Crystallogr A64:211

    Google Scholar 

  25. Farrugia LJ (2012) J Appl Crystallogr 45:849

    Article  CAS  Google Scholar 

  26. Gans J, Shalloway D (2001) J Mol Graph Model 19:557

    Article  CAS  Google Scholar 

  27. Brandenburg K (2006) DIAMOND. Version 3.1c. Crystal Impact GbR, Postfach 1251, D-53002 Bonn, Germany

  28. Spek AL (2003) J Appl Crystallogr 36:7

    Article  CAS  Google Scholar 

  29. Ferreira ML, de Souza MVN, Wardell SMSV, Tiekink ERT, Wardell JL (2012) Acta Crystallogr E68:o1214

    Google Scholar 

  30. de Souza MVN, Ferreira ML, Wardell SMSV, Tiekink ERT, Wardell JL (2012) Acta Crystallogr E68:o1244

    Google Scholar 

  31. Ferreira ML, de Souza MVN, Howie RA, Tiekink ERT, Wardell JL, Wardell SMSV (2010) Acta Crystallogr E66:o696

    Google Scholar 

  32. de Souza MVN, Howie RA, Tiekink ERT, Wardell JL, Wardell SMSV (2010) Acta Crystallogr E66:o152

    Google Scholar 

  33. de Souza MVN, Howie RA, Tiekink ERT, Wardel JL, Wardell SMSV, Kaiser CR (2010) Acta Crystallogr E66:o698

    Google Scholar 

  34. Ferreira ML, de Souza MVN, Howie RA, Tiekink ERT, Wardell JL, Wardell SMSV (2009) Acta Crystallogr E65:o3239

    Google Scholar 

  35. Allen FH (2002) Acta Crystallogr B58:380

    Article  CAS  Google Scholar 

  36. Yathirajan HS, Sarojini BK, Narayana B, Sunil K, Bolte M (2007) Acta Crystallogr E63:o2720

    Google Scholar 

  37. Jasinski JP, Butcher RJ, Narayana B, Sunil K, Yathirajan HS (2008) Acta Crystallogr E64:o481

    Google Scholar 

  38. de Souza MVN, Howie RA, Tiekink ERT, Wardell JL, Wardell SMSV (2009) Acta Crystallogr E65:o3204

    Google Scholar 

Download references

Acknowledgments

Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR-MOHE/SC/12) and the University of Malaya (UMRG125) for ERTT, and CNPq, Brazil for JLW is gratefully acknowledged.

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Authors and Affiliations

  1. Instituto de Tecnologia em Fármacos–Farmanguinhos, FioCruz–Fundacão, Oswaldo Cruz, R. Sizenando Nabuco, 100, Manguinhos, Rio de Janeiro, RJ, 21041-250, Brazil

    Marcelle de Lima Ferreira & Marcus V. N. de Souza

  2. Centre for Computational Physics, Department of Physics, University of Coimbra, Rua Larga, 3004-516, Coimbra, Portugal

    Bruce F. Milne

  3. Department of Chemistry, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Edward R. T. Tiekink

  4. Centro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundacão Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, Rio de Janeiro, RJ, 21040-900, Brazil

    James L. Wardell

  5. Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Aberdeen, Scotland

    James L. Wardell

  6. CHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland

    Solange M. S. V. Wardell

Authors
  1. Marcelle de Lima Ferreira
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  2. Bruce F. Milne
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  3. Marcus V. N. de Souza
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  4. Edward R. T. Tiekink
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  5. James L. Wardell
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Correspondence to James L. Wardell.

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de Lima Ferreira, M., Milne, B.F., de Souza, M.V.N. et al. Structures of Two Rotamers of the HCl Salt of 4-Methyl-2-[(1E)-[2-(quinolin-4-yl)hydrazin-1-ylidene]methyl]phenol: Different Supramolecular Arrays. J Chem Crystallogr 44, 36–41 (2014). https://doi.org/10.1007/s10870-013-0481-3

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