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Journal of Chemical Crystallography

, Volume 41, Issue 7, pp 1013–1017 | Cite as

Hydrogen Bonded Triple Helical Structure of 3-Hydroxyquinoxaline-2-carboxalidine-4-aminoantipyrine

  • V. Arun
  • G. P. Preetha
  • S. Manju
  • A. R. Biju
  • K. K. M. Yusuff
Original Paper

Abstract

The title compound, C20H17N5O2·2H2O, was synthesized by the condensation of 3-hydroxyquinoxaline-2-carboxaldehyde with 4-aminoantipyrine. The crystal structure was determined at 100 K. The molecule crystallizes in the amide tautomeric form with two molecules of lattice water in the trigonal space group P \( \overline{3} \) with a = 19.651(2) Å, c = 8.831(2) Å, Z = 6, V = 2953.3(9) Å3. Molecules assemble into a triple helix by intermolecular hydrogen bonds. The pitch distance of the helix is 26.493 Å. DFT calculations on gas phase models reveal that the iminol form of the compound is relatively stable by 3.1 kJ mol−1.

Graphical Abstract

Title compound, which was formed by the condensation of 3-hydroxyquinoxaline-2-carboxaldehyde and 4-aminoantipyrine, shows hydrogen bonded triple helix in the crystal lattice

Keywords

3-Hydroxyquinoxaline-2-carboxaldehyde 4-aminoantipyrine DFT calculations Triple helical crystal structure 

Notes

Acknowledgments

The authors thank Department of Science and Technology, India, for using the Sophisticated Analytical Instrumentation Facility (SAIF) at Indian Institute of Science, Bangalore (for 1H NMR spectrum) and at Sophisticated Test and Instrumentation Centre, Cochin University of Science and Technology, Cochin (for elemental analyses). A.R.B thanks UGC and S.M thanks Kerala State Council for Science, Technology and Environment for research fellowships. The X-ray data was collected on the diffractometer facilities at the University of Hyderabad provided by the Department of Science and Technology, Government of India. DFT calculations were performed using CMSD facility, University of Hyderabad. A.R.B. thanks Prof. M. V. Rajasekharan (School of Chemistry, University of Hyderabad) for support.

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • V. Arun
    • 1
  • G. P. Preetha
    • 1
  • S. Manju
    • 1
  • A. R. Biju
    • 2
    • 3
  • K. K. M. Yusuff
    • 1
  1. 1.Department of Applied ChemistryCochin University of Science and TechnologyCochinIndia
  2. 2.School of ChemistryUniversity of HyderabadHyderabadIndia
  3. 3.The Department of ChemistrySir Syed CollegeTaliparambaIndia

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