Single-Crystal Diffraction, Raman Spectroscopy, and Density Functional Theory of DTO [ N -(1,7-Dinitro-1,2,6,7-tetrahydro-[1,3,5]triazino[1,2- c ][1,3,5]oxadiazin-8(4H)-ylidene)nitramide].

A combined experimental and modeling study of energetic compound -(1,7-dinitro-1,2,6,7-tetrahydro-[1,3,5]triazino[1,2-][1,3,5]oxadiazin-8(4H)-ylidene)nitramide [CHNO, (DTO)] has been performed. We report its crystal structure, solid-phase heat of formation, and its vibrational and electronic structure obtained by single-crystal X-ray diffractometry, Raman spectroscopy, and density functional theory (DFT). DTO exhibits two adjoining six-membered rings, a triazine ring (CN) and an oxadiazine ring (CNO) ring containing two nitro functional groups and one nitroamino group. DTO crystallizes with four molecules in its unit cell and presents a density of 1.862 kg/m at 298 K, in excellent agreement with both DFT calculations performed both at the molecular level using the B3LYP with the 6-311+G** basis set and the solid-state level using the hybrid functional HSE6 optimized with norm-conserving pseudopotentials. The calculated vibrational structure allows for the symmetry assignment of key Raman modes in terms of atomic movements, and the calculated frequency values are in good agreement with experiment. The solid-phase DFT calculations reveal that the N atoms of the triazine ring contribute mostly to the density of states at the Fermi level. In addition, we present and discuss the computed solid-phase heat of formation (215.9 kJ/mol) and molecular electrostatic potential surface of DTO and compare them to complementary materials.