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.
Similar content being viewed by others
References
Calligaris, M.; Randaccio, L. Comprehensive Coordination Chemistry; G. Wilkinson Ed.; Pergamon: London, 1987; pp. 715–738.
Lozier, R.; Bogomolni, R.A.; Stoekenius, W. J. Biophys. 1975, 15, 955.
Garnovskii, A.D.; Nivorozhkin, A.L.; Minkin, V.I. Coord. Chem. Rev. 1993, 126, 1.
Costamagna, J.; Vargas, J.; Latorre, R.; Alvarado, A.; Mena, G. Coord. Chem. Rev. 1992, 119, 67.
Walsh, C.T.; Orme-Johnson, W.H. Biochemistry 1987, 26, 4901.
Hadjoudis, E.; Vitterakis, M.; Maviridis, I.M. Tetrahedron 1987, 43, 1345.
Nazır, H.; Yıldız, M.; Yılmaz, H.; Tahir, M.N.; Ülkü, D. J. Mol. Struct. 2000, 524, 241.
Antanov, L.; Fabian, W.M.F.; Nedeltcheva, D.; Kamounah, F.S. J. Chem. Soc. Perkin Trans., 2000, 2, 1173–1179.
Krygowski, T.M.; Wozniak, K.; Anulewicz, R.; Pawlak, D.; Kolodziejski, W.; Grech, E.; Szady, A. J. Phys. Chem. A 1997, 101, 9399.
Ogawa, K.; Harada, J. J. Mol. Struc. 2003, 647, 211.
Stoe & Cie, X-AREA (Version 1.18) and X-RED32 (Version 1.04), Darmstadt, Germany (2002).
Sheldrick, G.M. SHELXS 97 and SHELXL 97, Program for Crystal Structure Solution and Refinement; University of Göttingen: Germany, 1997.
Stewart, J.J. P. J. Comput. Chem. 1989, 10, 209.
Roothaan, C.C. J. Rev. Mod. Phys. 1951, 23, 69.
Shchepin, R.; Litvinov, D. WinMopac7.21, Program for semi-empirical calculations; Perm State University: Perm, Russia, 1998.
Farrugia, L.J. ORTEP-3 for Windows, Dept. of Chemistry: University of Glasgow: UK, 1998.
Spek, A.L., PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 2005.
Petek, H.; Albayrak, Ç.; Ağar, E.; Kalkan, H. Acta Cryst. 2006, E62, o3685.
Wojciechowski, G.; Ratajczak-Sitarz, M.; Katrusiak, A.; Schilf, W.; Przybylski, P.; Brzezinski, B. J. Mol. Struc. 2003, 650, 191.
Allen, F.H.; Kennard, O.; Watson, D.G.; Brammer, L.; Orpen, A.G.; Taylor, R. J. Cem. Soc., Perkin Trans. II 1987, S1.
Cremer, D.; Pople, J.A. J. Am. Chem. Soc. 1975, 97, 1354.
Ma, S-S.; Zhang, M-J.; Yuan, D-Y.; Qi, Z-B. Acta Cryst. 2005, E61, o1370.
Fun, H-K.; Chantrapromma, S.; Suni, V.; Sreekanth, A.; Sivakumar, S.; Prathapachandra Kurup, M.R. Acta Cryst. 2005, E61, o1337.
Bernstein, J.; Davis, R.E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555.
Acknowledgments
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).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Petek, H., Albayrak, Ç., İskeleli, N. et al. Crystallographic and conformational analyses of zwitterionic form of (E)-2-methoxy-6-[(2-morpholinoethylimino)methyl]phenolate. J Chem Crystallogr 37, 285–290 (2007). https://doi.org/10.1007/s10870-006-9175-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10870-006-9175-4