Estranes are a subclass of steroid, composed of eighteen carbon atoms with a gonane core. Its derivatives exhibit some notable biological properties. An attempt has been made here to investigate the crystal structure of four estrane derivatives as accessed from CSD database for their comparative crystallographic and quantum chemical analysis. These structures have been geometrically optimized using the density functional theory (DFT). The HOMO-LUMO energy gap, molecular electrostatic potential and Mulliken atomic charges have been computed using the same model. The energy band gap analysis suggested that all these structures are chemically stable. The Mulliken atomic charges and molecular electrostatic potential maps have been analyzed for the nucleophilic and electrophilic regions on the molecular surface. The three-dimensional dnorm plots from the Hirshfeld surface highlights the presence of C-H…O hydrogen bond interaction. The fingerprint plot analysis reveals the dominance of H…H contacts. The critical examination of crystal voids indicates the good mechanical stability for each structure. The molecular docking analysis suggests that the ligands 3-Oxoestran-17-yl acetate and 17β-Acetoxy 2β-bromo-5-methyl-5β-estran-3-one exhibit strong binding affinity towards the target protein Vitamin D3 receptor.