The stereochemistry of some halogenated steroids. Crystal structures of 8β-methyltestosterone 17β-monobromoacetate and testosterone 17β-p-bromobenzoate

Koyama, H.; Shiro, M.; Sato, Takaaki; Tsukuda, Y.; Itazaki, Hiroshi; Nagata, Wataru

doi:10.1039/c19670000812

Chem. Commun. (London)

1967

DOI: 10.1039/c19670000812

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The stereochemistry of some halogenated steroids. Crystal structures of 8β-methyltestosterone 17β-monobromoacetate and testosterone 17β-p-bromobenzoate

H. Koyama¹,

M. Shiro²,

Takaaki Sato³

et al.

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“…The vertical line is the plane defined by C(5), C(10), and C(19)molecules have all had the less bulky hydroxyl residue on the a-side of the molecule. A Dreiding model of (I) implies a distance of 2-80 between C(12) and C(22) and 3 25. between C(l4) and C(22), yet the…”

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Crystal and molecular structure of 6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstan-3-one

McKechnie¹,

Kubina²,

Paul³

1970

J. Chem. Soc. B

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6a-Bromo-I 7@-hydroxy-I 7a-methyl-Paul," W. A. Noyes Chemical Laboratory, University of The crystal and molecular structure of 6a-bromo-l7~-hydroxy-l7a-methyl-4-oxa-5a-androstan-3-one (I) has been determined by three-dimensional X-ray analysis. The crystals of (I) are orthorhombic with a = 12.23, b = 7.30, and c = 20.1 4 8, and the space group is P212121 with Z = 4. The structure has been refined to an R of 0.1 2 on 1500 reflexions collected photographically. The A : B, B : C, and C : D ring junctions are all trans. The tactone group in ring A is significantly non-planar with a C(2)-C(3)-0(4)-C(5) torsion angle of -23". Some comparisons are made with other molecules containing factone groups. The molecules in the crystal are linked in the c-directon by O-H * 0 hydrogen bonding.barely moved from its original position. Re-positioning the bromine atom so that the angles were more reasonable and calculating structure factors on the new position for bromine and the established positions for atoms of the A and B rings gave an R of 0.43. A Fourier map based on this calculation revealed the position of all the non-hydrogen atoms in the molecule with reasonable molecular dimensions.

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mentioning

confidence: 99%

Crystal and molecular structure of 6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstan-3-one

McKechnie¹,

Kubina²,

Paul³

1970

J. Chem. Soc. B

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The stereochemistry of some halogenated steroids. Crystal structures of 8β-methyltestosterone 17β-monobromoacetate and testosterone 17β-p-bromobenzoate

Cited by 1 publication

References 0 publications

Crystal and molecular structure of 6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstan-3-one

Crystal and molecular structure of 6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstan-3-one

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