Journal of Chemical Crystallography

, Volume 44, Issue 1, pp 36–41 | Cite as

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

  • Marcelle de Lima Ferreira
  • Bruce F. Milne
  • Marcus V. N. de Souza
  • Edward R. T. Tiekink
  • James L. Wardell
  • Solange M. S. V. Wardell
Original Paper
  • 96 Downloads

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.

Keywords

Rotomer Conformation Hydrogen bonding 

Notes

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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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Marcelle de Lima Ferreira
    • 1
  • Bruce F. Milne
    • 2
  • Marcus V. N. de Souza
    • 1
  • Edward R. T. Tiekink
    • 3
  • James L. Wardell
    • 4
    • 5
  • Solange M. S. V. Wardell
    • 6
  1. 1.Instituto de Tecnologia em Fármacos–Farmanguinhos, FioCruz–Fundacão, Oswaldo CruzRio de JaneiroBrazil
  2. 2.Centre for Computational Physics, Department of PhysicsUniversity of CoimbraCoimbraPortugal
  3. 3.Department of ChemistryUniversity of MalayaKuala LumpurMalaysia
  4. 4.Centro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundacão Oswaldo Cruz (FIOCRUZ)Rio de JaneiroBrazil
  5. 5.Department of ChemistryUniversity of AberdeenAberdeenScotland
  6. 6.CHEMSOLAberdeenScotland

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