TY - JOUR
T1 - 3-Oxoandrosta-4,6-dien-17beta-yl 2-methyl-1H-imidazole-1-carboxylate and 3-oxo-5alpha-androst-17beta-yl 2-methyl-1H-imidazole-1-carboxylate. C-H...pi and pi-pi intermolecular interactions
AU - Ramos Silva, Manuela
AU - Moreira, Vânia M
AU - Cardoso, Cláudia
AU - Matos Beja, Ana
AU - Salvador, Jorge A R
PY - 2009/3/15
Y1 - 2009/3/15
N2 - The title compounds, C(24)H(30)N(2)O(3), (I), and C(24)H(34)N(2)O(3), (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) degrees for molecule 1 of (I), 73.1 (3) degrees for molecule 2 of (I) and 86.63 (17) degrees 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.
AB - The title compounds, C(24)H(30)N(2)O(3), (I), and C(24)H(34)N(2)O(3), (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) degrees for molecule 1 of (I), 73.1 (3) degrees for molecule 2 of (I) and 86.63 (17) degrees 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.
KW - androstanes
KW - heterocyclic compounds, 4 or more rings
KW - molecular structure
U2 - 10.1107/S0108270109003278
DO - 10.1107/S0108270109003278
M3 - Article
C2 - 19265229
VL - C65
SP - o88-o91
JO - Acta Crystallographica Section C: Crystal Structure Communications
JF - Acta Crystallographica Section C: Crystal Structure Communications
SN - 0108-2701
IS - 3
ER -