N-tert-Butyl-3-hydroxy-5-androstene-17-carboxamide monohydrate

Jiang-Sheng Li,Xiao-Jun Li,Jim Simpson,Peng-Mian Huang,Xun Li

doi:10.1107/s1600536809020984

Abstract

In the title compound, C24H39NO2·H2O, the A and C rings of the pregnolene derivative sterol adopt chair conformations, with the B ring in a flattened chair conformation and the five-membered ring in an envelope conformation twisted about the C/D ring junction. The N-tert-butylcarboxamide substituent is equatorial. The 3β-hydroxy H atom and one H atom of the water molecule are disordered over two positions with equal occupancies. In the crystal structure, O—H⋯O hydrogen bonds between the 3β-hydroxy groups of neighbouring molecules form dimers in the bc plane and these dimers are stacked along the a axis by additional O—H⋯O hydrogen bonds involving the water molecules. The steric effect of the bulky tert-butyl substituent in the carboxamide chain precludes hydrogen-bond formation by the N—H group.

Highlights

In the title compound, C24H39NO2H2O, the A and C rings of the pregnolene derivative sterol adopt chair conformations, with the B ring in a flattened chair conformation and the fivemembered ring in an envelope conformation twisted about the
The 3-hydroxy H atom and one H atom of the water molecule are disordered over two positions with equal occupancies
O—H O hydrogen bonds between the 3-hydroxy groups of neighbouring molecules form dimers in the bc plane and these dimers are stacked along the a axis by additional O—H O hydrogen bonds involving the water molecules

Summary

Structure Reports

Peng-Mian Huanga a School of Chemistry and Biological Engineering, Changsha University of Science &. Technology, Changsha 410004, People’s Republic of China, bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand, and cSchool of Chemical Engineering, Hebei University of Technology, Tianjin 300130, People’s

Data collection

Related literature

Graphite monochromator φ and ω scans

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