ABSTRACT
In the title compound, C(17)H(27)NO(4), which is an hydro-sinapic acid derivative with increased lipophilicity conferred by an additional alkyl chain, the central and the hexyl linear chains contain slightly shorter bond lengths [C-N = 1.316â (2)â Å; average linear chain C-C = 1.487â (6)â Å] than reported average values [Csp(2)-N = 1.334, C-C for CH(2)-CH(2) = 1.524 and 1.513â Å for CH(2)-CH(3)]. The 4-hy-droxy-3,5-dimeth-oxy-phenyl plane [r.m.s. deviation 0.055â (12)â Å] makes an angle of 59.89â (5)° with the central plane of the mol-ecule (composed of the N atom, the carbonyl group and the two methyl-ene C atoms linking the carbonyl group and the ring, [r.m.s. deviation 0.0026â (10)â Å], which, in turn, makes an angle of 64.24â (13)° with the essentially planar hexyl chain [r.m.s. deviation 0.035â (18)â Å]. The N-H group of the amide group is involved in a bifurcated hydrogen bond towards the hy-droxy and one of the meth-oxy O atoms of the 4-hy-droxy-3,5-dimeth-oxy-phenyl substituent of a neighbouring mol-ecule, forming a two-dimensional network in the (100) plane. In addition, the same hy-droxy group acts as a donor towards the carbonyl O atom of another neighbouring mol-ecule, forming chains running along the b axis.
ABSTRACT
In the title compound, C(20)H(26)O(2), which is the 6-methyl-ene derivative of androstenedione and a synthetic percursor of exemestane, the steroid A ring approximates to a sofa (or envelope) conformation, with the methyl-ene group adjacent to the link to the B ring lying out of the plane of the other atoms. The B and C rings have slightly flattened chair conformations and the D ring is an envelope, with the CH group forming the flap. In the crystal, mol-ecules are linked by two distinct C-Hâ¯O hydrogen bonds, involving acidic H atoms close to C=C and C=O double bonds.
ABSTRACT
In the crystal structure of the title compound, C(21)H(32)O(2), ring A is highly distorted, with a conformation inter-mediate between 10ß-sofa and 1α,10ß-half chair; rings B and C have slightly flattened chair conformations. Ring D assumes an unusual 13ß-envelope conformation, probably induced by the acet-oxy substituent. Cohesion of the crystal structure is due only to weak van der Waals inter-actions.
ABSTRACT
The title compound, C(21)H(32)O(3), results from modifications of the A and D rings of the aromatase substrate androstenedione. Ring A adopts a conformation between 10ß-sofa and 1α,10ß half-chair. Rings B and C are in slightly flattened chair conformations. Ring D approaches a 13ß-envelope conformation, probably due to the acet-oxy substituent, and shows a very short Csp(3)-Csp(3) bond next to the epoxide ring, which is characteristic of 3-4 epoxides. .
ABSTRACT
The title compound, C(19)H(29)NO, is a C17-oxime derivative of a potent aromatase inhibitor, which surprisingly has been found to have no inhibitory power. It crystallizes with two independent molecules in the asymmetric unit. C=N-O-H...N hydrogen bonds link pairs of molecules to form dimers almost parallel to the bc plane. Cohesion of the structure is also due to another three C-H...O hydrogen bonds directed along the a axis. This hydrogen-bonding scheme can be correlated to the almost complete loss of inhibitory power of the title compound.
Subject(s)
17-Ketosteroids/chemistry , Aromatase Inhibitors/chemistry , Oximes/chemistry , Crystallography, X-Ray , Hydrogen Bonding , Molecular ConformationABSTRACT
The title compound, C(21)H(28)O(4), has a 4-acetoxy substituent positioned on the steroid alpha face. The six-membered ring A assumes a conformation intermediate between 1alpha,2beta-half chair and 1alpha-sofa. A long Csp(3)-Csp(3) bond is observed in ring B and reproduced in quantum-mechanical ab initio calculations of the isolated molecule using a molecular-orbital Hartree-Fock method. Cohesion of the crystal can be attributed to van der Waals interactions and weak C-H...O hydrogen bonds.
Subject(s)
Acetates/chemistry , Androstenedione/analogs & derivatives , Androstenes/chemistry , Crystallography, X-Ray , Molecular ConformationABSTRACT
The title compounds, both C23H34O5, are the 5alpha and 5beta configurations of two diacetate epimers. The 5beta-diacetate crystallizes in an hexagonal structure, unusual for steroid molecules. The unit cell has an accessible solvent volume of 358 A(3), responsible for clathrate behaviour. The 5beta-epimer also features some shorter than average bond lengths in the 3alpha,4beta-acetoxy groups. The conformations of the molecules of both epimers are compared with those obtained through ab initio quantum chemistry calculations. Cohesion of the crystals can be attributed to van der Waals and weak molecular C-H...O interactions.
