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Density, detonation property, and sensitivity may be the most valued features when evaluating an energetic material. By reasoning structure–property relationships, a nitro-free planar energetic material with high nitrogen and oxygen content, 7-hydroxy-difurazano[3,4- b :3′,4′- f ]furoxano[3″,4″- d ]azepine ( 4 ), was synthesized using a unique and facile approach. The structure was fully characterized by IR and NMR spectra, elemental analysis, differential scanning calorimetry (DSC), and single-crystal X-ray diffraction. The expected properties of  4 , including a high density of 1.92 g cm −3 , high detonation velocity of 8,875 m s −1 , and low mechanical sensitivities (impact sensitivity, 21 J and friction sensitivity, >360 N), confirm our strategy. Interestingly, the single-crystal structures of  4  reveal expected face-to-face and edge-to-face π-interactions in the crystal stacking. The remarkable differences in crystal stacking of  4  provide unequivocal evidence that face-to-face π-π interactions contribute significantly to closer assembly and higher density.

The Ingenious Synthesis of a Nitro-Free Insensitive High-Energy Material Featuring Face-to-Face and Edge-to-Face π-Interactions