Density function theory (DFT) and experimental characterization of energetic materials play important roles in understanding molecular structure-property relations and validating models for their predictive capabilities. Here, we report our modeling and experimental results on the molecular, vibrational, and crystal structure of energetic bis-oxadiazole-bis-methylene dinitrate (BODN) obtained by molecular DFT (M-DFT) at the B3LYP- 6-31G** level, crystal DFT (C-DFT) using the Perdew-Burke-Ernzerhof functional optimized with norm-conserving pseudopotentials, X-ray diffractometry, infrared and Raman spectroscopy, and thermogravimetric analysis. Both models predict well the experimental bond lengths, bond angles, and torsion angles of BODN. The C-DFT lattice constant values are in excellent agreement with those determined experimentally, with unit cell length and angle values differing by less than 1.2 and 0.7%, respectively. BODN presents van der Waals O center dot center dot center dot H and O center dot center dot center dot C bifurcated intramolecular contacts and short N center dot center dot center dot H and O center dot center dot center dot O intermolecular contacts. Overall, the predicted vibrational energies of both models are in line with experiment. M-DFT thermodynamic calculations predict well the experimentally derived lattice energy (-131 kJ/mol) and the M-DFT electrostatic potential calculations reveal a low sensitivity to impact. In addition, C-DFT band gap calculations predict a value of 3.80 eV for BODN, resulting predominantly from the ring O and N atoms, suggesting it is insensitive to impact. These results are compared and contrasted with those obtained in this study or reported previously for 3,3-bis-isoxazole-5,5'-bis-methylene dinitrate (BIDN).