Androstane-3β,5α,6β,17β-tetrol tri-hydrate.

Area of Science:

• Steroid chemistry
• Crystallography
• Quantum chemistry

Background:

• The synthesis of complex organic molecules often requires stereoselective methods.
• Understanding the intermolecular interactions in crystalline solids is crucial for predicting material properties.

Purpose of the Study:

• To synthesize and characterize a hydrated tetrol derivative.
• To investigate the crystal structure and hydrogen bonding of the synthesized compound.
• To compare experimental molecular geometry with theoretical calculations.

Main Methods:

• Stereoselective reduction of 3β,5α,6β-trihydroxy-androstan-17-one.
• X-ray crystallography for structure determination.
• Quantum chemical ab initio Roothan Hartree-Fock calculations.

Main Results:

• Successful synthesis of hydrated tetrol, C(19)H(32)O(4)·3H(2)O.
• Crystal structure reveals trans-fused rings and head-to-tail hydrogen bonding along the c axis.
• Water molecules form layers in the ab plane, interconnecting the hydrogen-bonded chains.
• Theoretical calculations closely match experimental geometry, except for C-O bond lengths.

Conclusions:

• The synthesized hydrated tetrol exhibits a well-defined crystal structure with extensive hydrogen bonding.
• Discrepancies in C-O bond lengths suggest the influence of hydrogen bonding on molecular geometry.
• Computational methods provide valuable insights into the structure and bonding of organic crystals.