Conformation of 17-Chloro-16-formylandrosta-5,16-dien-3β-yl acetate and 17-chloroandrosta-5,16-dien-3β-yl acetate

Manuela R. Silva, Vania M. Moreira, Cláudia Cardoso, Ana Matos Beja, Jorge A. R. Salvador

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

In the title compounds, C22H29ClO3, (I), and C21H29ClO2, (II), respectively, the B rings adopt a half-chair conformation and the D rings adopt an envelope conformation. A twist of the steroid skeleton of both compounds is observed. There is a positional disorder of the acetoxy group of (II), with the terminal atoms disordered over two positions with near equal occupancy. Quantum-mechanical ab initio calculations using a molecular orbital Hartree–Fock method were performed for the isolated molecules, thus allowing the distinction within the structural features of these two androstane derivatives of which characteristics are intrinsic to the molecules and which are due to packing effects. The skeletal twisting was found to be innate to the molecules, while the acetoxy disorder is due to packing effects.
LanguageEnglish
Pageso529-o531
Number of pages3
JournalActa Crystallographica Section C: Crystal Structure Communications
VolumeC64
Issue number9
Early online date29 Aug 2008
DOIs
Publication statusPublished - 15 Sep 2008

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Skeleton
Conformations
Steroids
Molecules
Molecular orbitals
Derivatives
Atoms
17-chloro-16-formylandrosta-5,16-dien-3beta-yl acetate
17-chloroandrosta-5,16-dien-3beta-yl acetate
androstane

Keywords

  • 17-oxoandrost-5-en-3β-yl acetate
  • C22H29ClO3
  • C21H29ClO2

Cite this

@article{7c23a801b536431683d54fa6bac1fef5,
title = "Conformation of 17-Chloro-16-formylandrosta-5,16-dien-3β-yl acetate and 17-chloroandrosta-5,16-dien-3β-yl acetate",
abstract = "In the title compounds, C22H29ClO3, (I), and C21H29ClO2, (II), respectively, the B rings adopt a half-chair conformation and the D rings adopt an envelope conformation. A twist of the steroid skeleton of both compounds is observed. There is a positional disorder of the acetoxy group of (II), with the terminal atoms disordered over two positions with near equal occupancy. Quantum-mechanical ab initio calculations using a molecular orbital Hartree–Fock method were performed for the isolated molecules, thus allowing the distinction within the structural features of these two androstane derivatives of which characteristics are intrinsic to the molecules and which are due to packing effects. The skeletal twisting was found to be innate to the molecules, while the acetoxy disorder is due to packing effects.",
keywords = "17-oxoandrost-5-en-3β-yl acetate, C22H29ClO3, C21H29ClO2",
author = "Silva, {Manuela R.} and Moreira, {Vania M.} and Cl{\'a}udia Cardoso and {Matos Beja}, Ana and Salvador, {Jorge A. R.}",
year = "2008",
month = "9",
day = "15",
doi = "10.1107/S0108270108025997",
language = "English",
volume = "C64",
pages = "o529--o531",
journal = "Acta Crystallographica Section C: Crystal Structure Communications",
issn = "0108-2701",
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}

Conformation of 17-Chloro-16-formylandrosta-5,16-dien-3β-yl acetate and 17-chloroandrosta-5,16-dien-3β-yl acetate. / Silva, Manuela R.; Moreira, Vania M.; Cardoso, Cláudia; Matos Beja, Ana; Salvador, Jorge A. R.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. C64, No. 9, 15.09.2008, p. o529-o531.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Conformation of 17-Chloro-16-formylandrosta-5,16-dien-3β-yl acetate and 17-chloroandrosta-5,16-dien-3β-yl acetate

AU - Silva, Manuela R.

AU - Moreira, Vania M.

AU - Cardoso, Cláudia

AU - Matos Beja, Ana

AU - Salvador, Jorge A. R.

PY - 2008/9/15

Y1 - 2008/9/15

N2 - In the title compounds, C22H29ClO3, (I), and C21H29ClO2, (II), respectively, the B rings adopt a half-chair conformation and the D rings adopt an envelope conformation. A twist of the steroid skeleton of both compounds is observed. There is a positional disorder of the acetoxy group of (II), with the terminal atoms disordered over two positions with near equal occupancy. Quantum-mechanical ab initio calculations using a molecular orbital Hartree–Fock method were performed for the isolated molecules, thus allowing the distinction within the structural features of these two androstane derivatives of which characteristics are intrinsic to the molecules and which are due to packing effects. The skeletal twisting was found to be innate to the molecules, while the acetoxy disorder is due to packing effects.

AB - In the title compounds, C22H29ClO3, (I), and C21H29ClO2, (II), respectively, the B rings adopt a half-chair conformation and the D rings adopt an envelope conformation. A twist of the steroid skeleton of both compounds is observed. There is a positional disorder of the acetoxy group of (II), with the terminal atoms disordered over two positions with near equal occupancy. Quantum-mechanical ab initio calculations using a molecular orbital Hartree–Fock method were performed for the isolated molecules, thus allowing the distinction within the structural features of these two androstane derivatives of which characteristics are intrinsic to the molecules and which are due to packing effects. The skeletal twisting was found to be innate to the molecules, while the acetoxy disorder is due to packing effects.

KW - 17-oxoandrost-5-en-3β-yl acetate

KW - C22H29ClO3

KW - C21H29ClO2

U2 - 10.1107/S0108270108025997

DO - 10.1107/S0108270108025997

M3 - Article

VL - C64

SP - o529-o531

JO - Acta Crystallographica Section C: Crystal Structure Communications

T2 - Acta Crystallographica Section C: Crystal Structure Communications

JF - Acta Crystallographica Section C: Crystal Structure Communications

SN - 0108-2701

IS - 9

ER -