Abstract
The crystal structures of two forms of 17β-(2-hydroxyethyl)-3-pyrrolidino-17a-aza-D-homo-5-androstene (HS-625) are reported. In HS-625 (aqueous solvate) form 1, moleculeA, and HS-625 (anhydride) form 2, moleculeB, the pyrrolidine group is 3-β substituted, while in HS-625 (anhydride) form 2, moleculeC has its pyrrolidine ring α-substituted. HS-625 form 1 is orthorhombic, space groupP212121, witha=7.089(4),b=11.502(6),c=28.975(16) Å,Z=4; form 2 is triclinic, space groupP1, witha=14.013(8),b=12.572(6),c=6.688(4) Å, α=95.187(20), β=103.491(21); γ=86.210(20)°,Z=2. MoleculesA andB have similar geometry, differences in moleculeC being related to strain caused by the unusual 3-α ring substituent which also produces a pronounced kink in the backbone of the molecule. An unusual feature of the analysis of form 1 is the location of the water hydrogens in the difference electron density well above background. None of the OH hydrogens was located. Both structures are hydrogen bonded, but the pyrrolidine nitrogen N(31) in moleculeC is heavily congested and is unable to act as an acceptor. The hydroxyethyl side chain, important for activity, has a different conformation in the three molecules (t,g, t,-g, andt,t respectively).
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Braun, P. B., Hornstra, J., and Leenhouts, J. I. (1969)Phillips Res. Rep. 24, 85–118.
Codding, P. W., and James, M. N. G. (1973)Acta Cryst. B 29, 935–942.
Datta, N., Mondal, P., and Pauling, P. (1980)Acta Cryst. B 36, 906–909.
Declercq, J. P., Germain, G., and Woolfson, M. M. (1979)Acta. Cryst. A 35, 622–626.
El-Shora, A. I. (1982) Ph.D. Thesis (University of London).
El-Shora, A. I., Palmer, R. A., Singh, H., Bhardwaj, T. R., and Paul, D. (1982)J. Cryst. Spectrosc. Res. 3, 255–270.
Gandiha, A., Marshall, I. G., Paul, D., and Singh, H. (1974)J. Pharm., Pharmacol. 26, 871–877.
Giglio, E. (1969)Nature,222, 339–341.
Hornstra, J. (1972) Philips National Laboratory Reports Nos. 4701 and 4702.
Husain, J., Palmer, R. A., and Tickle, I. J. (1981)J. Cryst. Mol. Struct. 11, 87–103.
Husain, J., Tickle, I. J., Palmer, R. A., Singh, H., Bhardwaj, T. R., and Paul, D. (1982)Acta Cryst. B 38, 130–135.
International Tables for X-ray Crystallography (1962) Vol. III (Kynoch Press, Birmingham, England).
Ladd, M. F. C. (1973) Personal communication.
Marshall, I. G., Harvey, A. L., Singh, H., Bhardwaj, T. R., and Paul, D. (1981)J. Pharm. Pharmacol. 33, 451–457.
Mazid, M. A., Palmer, R. A., Singh, H., and Paul, D. (1977)Acta Cryst. B 33, 3641–3649.
Momany, F. A., Carruthers, L. M., McGuire, R. F., and Scheraga, H. A. (1973)J. Phys. Chem. 76, 1595–1620.
Motherwell, W. D. S. (1974)Eeny-“A Potential Energy Program” (University Chemical Laboratory, Cambridge).
Reynolds, C. D., and Palmer, R. A. (1976)Acta Cryst. B 32, 1431–1439.
Rohrer, D. C., and Fullerton, D. S. (1980)Acta Cryst. B 36, 1565–1568.
Singh, H., Bhardwaj, T. R., and Paul, D. (1979)J. Chem. Soc. Perkin Trans. 2451–2454.
Wipke, W. T., and Gund, P. (1974)J. Am. Chem. Soc. 96, 299–301.
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El-Shora, A.I., Palmer, R.A., Singh, H. et al. Steroids and related studies. Part 60. Crystal and molecular structures of 17β-(2-hydroxyethyl)-3β-and 3α-pyrrolidino-17a-aza-D-homo-5-androstenes: HS-625 form 1, (3β-pyrrolidino) and HS-625 form 2 (mixed-3α and -3β-pyrrolidino epimers). Journal of Crystallographic and Spectroscopic Research 14, 89–115 (1984). https://doi.org/10.1007/BF01161425
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DOI: https://doi.org/10.1007/BF01161425