3-Oxoandrosta-4,6-dien-17[beta]-yl 2-methyl-1H-imidazole-1-carboxylate and 3-oxo-5[alpha]-androst-17[beta]-yl 2-methyl-1H-imidazole-1-carboxylate: C-H...[pi] and [pi]-[pi] intermolecular interactions

• Autor(a) principal: Silva, Manuela Ramos
• Data de Publicação: 2009
• Outros Autores: Moreira, Vânia M., Cardoso, Cláudia, Beja, Ana Matos, Salvador, Jorge A. R.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/10316/12970

The title compounds, C24H30N2O3, (I), and C24H34N2O3, (II), both contain an androstane backbone and a 2-methylimidazole-1-carboxylate moiety at the 17-position. Compound (I) contains two symmetry-independent molecules (denoted 1 and 2), while compound (II) contains just one molecule in the asymmetric unit. The C-C-O-C torsion angle that reflects the twisting of the 2-methylimidazole-1-carboxylate moiety from the mean steroid plane is 143.1 (2)° for molecule 1 of (I), 73.1 (3)° for molecule 2 of (I) and 86.63 (17)° for (II). The significance of this study lies in its observation of significant differences in both molecular conformation and supramolecular aggregation between the molecules of the title compounds. The solid-state conformations compared with those obtained theoretically from ab initio methods for the isolated molecules show large differences, especially in the orientation of the methylimidazole substituent