Journal of Chemical Crystallography

, Volume 37, Issue 4, pp 285–290 | Cite as

Crystallographic and conformational analyses of zwitterionic form of (E)-2-methoxy-6-[(2-morpholinoethylimino)methyl]phenolate

  • Hande Petek
  • Çiğdem Albayrak
  • Nazan Ocak İskeleli
  • Erbil Ağar
  • İsmet Şenel
Original Paper

The single crystal X-ray diffraction analysis of the title compound, C14H20N2O3, reveals that the structure is adapted to its zwitterionic form and \(R_2^2 (12)\) centrosymmetric dimers are formed by N+–H···O type ionic weak hydrogen bonds in the crystal structure. The title compound crystallizes in the triclinic space group P−1 with a = 5.9255(13) Å, b = 9.853(3) Å, c = 12.248(3) Å, α = 101.793(19)°, β = 94.941(17)°, γ = 104.36(2)°, Z = 2, Dx = 1.308 g/cm3, μ (Mo-Kα) = 0.092 mm−1. The structure was solved by direct methods and refined to a final R = 0.0371 for 2183 reflections with I > 2σ (I). The crystal structure is stabilized by N+–H···O type intra-molecular hydrogen bonds and N+–H···O type packing interactions referred to as weak hydrogen bonds. To elucidate conformational flexibility of the title molecule, the selected torsion angle is varied from −180° to +180° in every 10° separately and then molecular energy profile is calculated and construed. In addition, charge-population analysis of the crystallographically observed structure confirms its zwitterionic form.


crystal structure schiff base morpholine zwitterion PM3 conformational analysis 



The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the STOE IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).


  1. 1.
    Calligaris, M.; Randaccio, L. Comprehensive Coordination Chemistry; G. Wilkinson Ed.; Pergamon: London, 1987; pp. 715–738.Google Scholar
  2. 2.
    Lozier, R.; Bogomolni, R.A.; Stoekenius, W. J. Biophys. 1975, 15, 955.CrossRefGoogle Scholar
  3. 3.
    Garnovskii, A.D.; Nivorozhkin, A.L.; Minkin, V.I. Coord. Chem. Rev. 1993, 126, 1.CrossRefGoogle Scholar
  4. 4.
    Costamagna, J.; Vargas, J.; Latorre, R.; Alvarado, A.; Mena, G. Coord. Chem. Rev. 1992, 119, 67.CrossRefGoogle Scholar
  5. 5.
    Walsh, C.T.; Orme-Johnson, W.H. Biochemistry 1987, 26, 4901.Google Scholar
  6. 6.
    Hadjoudis, E.; Vitterakis, M.; Maviridis, I.M. Tetrahedron 1987, 43, 1345.Google Scholar
  7. 7.
    Nazır, H.; Yıldız, M.; Yılmaz, H.; Tahir, M.N.; Ülkü, D. J. Mol. Struct. 2000, 524, 241.Google Scholar
  8. 8.
    Antanov, L.; Fabian, W.M.F.; Nedeltcheva, D.; Kamounah, F.S. J. Chem. Soc. Perkin Trans., 2000, 2, 1173–1179.Google Scholar
  9. 9.
    Krygowski, T.M.; Wozniak, K.; Anulewicz, R.; Pawlak, D.; Kolodziejski, W.; Grech, E.; Szady, A. J. Phys. Chem. A 1997, 101, 9399.Google Scholar
  10. 10.
    Ogawa, K.; Harada, J. J. Mol. Struc. 2003, 647, 211.Google Scholar
  11. 11.
    Stoe & Cie, X-AREA (Version 1.18) and X-RED32 (Version 1.04), Darmstadt, Germany (2002).Google Scholar
  12. 12.
    Sheldrick, G.M. SHELXS 97 and SHELXL 97, Program for Crystal Structure Solution and Refinement; University of Göttingen: Germany, 1997.Google Scholar
  13. 13.
    Stewart, J.J. P. J. Comput. Chem. 1989, 10, 209.Google Scholar
  14. 14.
    Roothaan, C.C. J. Rev. Mod. Phys. 1951, 23, 69.Google Scholar
  15. 15.
    Shchepin, R.; Litvinov, D. WinMopac7.21, Program for semi-empirical calculations; Perm State University: Perm, Russia, 1998.Google Scholar
  16. 16.
    Farrugia, L.J. ORTEP-3 for Windows, Dept. of Chemistry: University of Glasgow: UK, 1998.Google Scholar
  17. 17.
    Spek, A.L., PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 2005.Google Scholar
  18. 18.
    Petek, H.; Albayrak, Ç.; Ağar, E.; Kalkan, H. Acta Cryst. 2006, E62, o3685.Google Scholar
  19. 19.
    Wojciechowski, G.; Ratajczak-Sitarz, M.; Katrusiak, A.; Schilf, W.; Przybylski, P.; Brzezinski, B. J. Mol. Struc. 2003, 650, 191.Google Scholar
  20. 20.
    Allen, F.H.; Kennard, O.; Watson, D.G.; Brammer, L.; Orpen, A.G.; Taylor, R. J. Cem. Soc., Perkin Trans. II 1987, S1.Google Scholar
  21. 21.
    Cremer, D.; Pople, J.A. J. Am. Chem. Soc. 1975, 97, 1354.Google Scholar
  22. 22.
    Ma, S-S.; Zhang, M-J.; Yuan, D-Y.; Qi, Z-B. Acta Cryst. 2005, E61, o1370.Google Scholar
  23. 23.
    Fun, H-K.; Chantrapromma, S.; Suni, V.; Sreekanth, A.; Sivakumar, S.; Prathapachandra Kurup, M.R. Acta Cryst. 2005, E61, o1337.Google Scholar
  24. 24.
    Bernstein, J.; Davis, R.E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555.Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Hande Petek
    • 1
  • Çiğdem Albayrak
    • 2
  • Nazan Ocak İskeleli
    • 3
  • Erbil Ağar
    • 2
  • İsmet Şenel
    • 1
  1. 1.Department of PhysicsFaculty of Arts and Sciences, Ondokuz Mayıs UniversityKurupelitTurkey
  2. 2.Department of ChemistryFaculty of Arts and Sciences, Ondokuz Mayıs UniversityKurupelitTurkey
  3. 3.Department of Science EducationSinop Faculty of Education, Ondokuz Mayıs UniversitySinopTurkey

Personalised recommendations