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In energetic materials, the crystal density is an important parameter that affects the performance of the material. When making ionic energetic materials, the choice of counter-ion can have detrimental or beneficial effects on the packing, and therefore the density, of the resulting energetic crystal. Presented herein are a series of five ionic energetic crystals, all containing the dianion 5,5'-(3,3'-bi[1,2,4-oxa-diazole]-5,5'-di-yl)bis-(1 H -tetra-zol-1-olate), with the following cations: hydrazinium ( 1 ) (2N 2 H 5  + ·C 6 N 12 O 4  2- ), hydroxyl-ammonium ( 2 ) 2NH 4 O + ·C 6 N 12 O 4  2- [Pagoria et al.. (2017). Chem. Heterocycl. Compd , 53 , 760-778; included for comparison], di-methyl-ammonium ( 3 ) (2C 2 H 8 N + ·C 6 N 12 O 4  2- ), 5-amino-1 H -tetra-zol-4-ium ( 4 ) (2CH 4 N 5  + ·C 6 N 12 O 4  2- ·4H 2 O), and amino-guanidinium ( 5 ) (2CH 7 N 4  + ·C 6 N 12 O 4  2- ). Both the supra-molecular inter-actions and the sterics of the cation play a role in the density of the resulting crystals, which range from 1.544 to 1.873 Mg m -1 . In 5 , the tetra-zolate ring is disordered over two positions [occupancy ratio 0.907 (5):0.093 (5)] due to a 180° rotation in the terminal tetra-zole rings.

acta crystallographica. section e, crystallographic communications

Effect of counter-ion on packing and crystal density of 5,5′-(3,3′-bi[1,2,4-oxadiazole]-5,5′-diyl)bis(1<i>H</i>-tetrazol-1-olate) with five different cations

Effect of counter-ion on packing and crystal density of 5,5′-(3,3′-bi[1,2,4-oxadiazole]-5,5′-diyl)bis(1H-tetrazol-1-olate) with five different cations