Abstract
Compound (I) is 2-methyl-3-(2′-methyl-2′-nitrovinyl)indole, C12H12N2O2,M r=216.24, monoclinic,P21/n,a=16.710(1),b=7.627(1),c=17.646(1) Å,β=104.8(1)°,V=2174.7(1) Å3,Z=8.D x=1.321 g cm−3, MoKα, λ=0.71073 Å,μ=0.858 cm−1,F(OOO)=912, room temperature,R=0.061 for 1956 observed reflections. Compound (II) is 3-(2′-nitrovinyl)indole, C10H8N2O2,M r=188.18, monoclinic,P21/n,a=10.178(1),b=10.608(1),c=8.411(1) Å,β=105.5(2)°,V=875.0(1) Å3,Z=4,D x=1.4284 g cm−3, CuKα, γ=1.5418 Å,μ=8.068 cm−1,F(000)=392, room temperature,R=0.040 for 1330 observed reflections. Compounds (I) and (II) have a similar geometry, the only significant difference lying in the rotation of the nitrovinyl chain. This feature could be responsible for the difference in biological activity. In both compounds, the molecules are associated, forming charge-transfer complexes.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ash, A. S. F., and Wragg, W. R. (1958)J. Chem. Soc., 3887–3892.
Bucki, G. and Ching-Pong Mak (1977)J. Org. Chem. 42, 1784–1786.
Fonseca, I., Martinez-Carrera, S., Garcia-Blanco, S., and Rodriguez, J. G. (1987)Acta Crystallogr. C 43, 1613–1615.
Foster, R. (1973)Molecular Complexes, Vol. 1 (Eleck Sci., London).
International Tables for X-ray Crystallography (1974) Vol. IV (Kynoch Press, Birmingham, England).
Main, P., Fiske, S. J., Hull, S. E., Lessinger, L., Germain, G., Declercq, J. P., and Woolfson, M. H. (1980)Multan. System of Computer Programs for Automatic Solution of Crystal Structures from X-ray Diffraction Data (Univ. of York, England, and Louvain, Belgium).
Martinez-Ripoll, M., and Cano, F. H. (1975)Pesos. A Computer Program for Automatic Treatment of Weighting Schemes (Instituto Rocasolano, Madrid, Spain).
Nardelli, M. (1983)Comp. Chem. 7, 95–97.
Patai, S. (1969)The Chemistry of Functional Groups. The Nitro and Nitroso Groups (Wiley, New York), pp. 37–40.
Rodriguez, J. G., Temprano, F., Esteban-Calderon, C., Martinez-Ripoll, M., and Garcia-Blanco, S. (1985)Tetrahedron 41, 3813–3823.
Stewart, J. M., Kundell, F. A., and Baldwin, J. C. (1970) TheXray System (Computer Science Center, Univ. of Maryland).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Fonseca, I., Martinez-Carrera, S., Garcia-Blanco, S. et al. Structural study of nitrovinylindoles: (I) 2-methyl-3-(2′-methyl-2′-nitrovinyl)indole and (II) 3-(2′-nitrovinyl)indole. Journal of Crystallographic and Spectroscopic Research 18, 265–275 (1988). https://doi.org/10.1007/BF01194317
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF01194317