Acta Crystallographica Section C

Crystal Structure Communications

Volume 58, Part 2 (February 2002)

Acta Cryst. (2002). C58, o63-o65 [doi:10.1107/S0108270101018182]

D-Secoestrone derivatives. V. 3-Methoxy-17-oxo-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile and 17-hydroxy-3-methoxy-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile

D. Lazar, S. Stankovic, V. Pejanovic and C. Courseille

Abstract: The two title 16,17-secoestrone derivatives, 3-methoxy-17-oxo-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile, C₂₅H₂₇NO₂, (I) (17-oxo substituent), and 17-hydroxy-3-methoxy-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile, C₂₅H₂₉NO₂, (II) (17-hydroxy substituent), have quite different conformations in the solid state. These conformational differences can be minimized by molecular mechanics calculations. Thus, the remarkable difference in the biological activity of the two compounds, e.g. the strong oestrogenic characteristics of (I) and the moderate antioestrogenic action of (II), must be caused by the difference in substitution at C17. In (II), the molecules are linked by O-HN hydrogen bonds, forming spirals along the b direction.

Formula: C₂₅H₂₇NO₂ and C₂₅H₂₉NO₂

Online 16 January 2002


	Structure factor file (CIF format) (79.7 kbytes) Contains datablock I

	Structure factor file (CIF format) (58.8 kbytes) Contains datablock II

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