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

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-oxadiazole]-5,5′-diyl)bis(1 H -tetrazol-1-olate), with the following cations: hydrazinium ( 1 ) (2N 2 H 5 + ·C 6 N 12 O 4 2− ), hydroxylammonium ( 2 ) 2NH 4 O + ·C 6 N 12 O 4 2− [Pagoria et al.. (2017). Chem. Heterocycl. Compd , 53 , 760–778; included for comparison], dimethylammonium ( 3 ) (2C 2 H 8 N + ·C 6 N 12 O 4 2− ), 5-amino-1 H -tetrazol-4-ium ( 4 ) (2CH 4 N 5 + ·C 6 N 12 O 4 2− ·4H 2 O), and aminoguanidinium ( 5 ) (2CH 7 N 4 + ·C 6 N 12 O 4 2− ). Both the supramolecular interactions 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 ,more » the tetrazolate ring is disordered over two positions [occupancy ratio 0.907 (5):0.093 (5)] due to a 180° rotation in the terminal tetrazole rings.« less
Authors:
ORCiD logo [1] ;  [2] ; ORCiD logo [2] ;  [1] ;  [2]
  1. Naval Research Lab. (NRL), Washington, DC (United States). Center for Biomolecular Science and Engineering (CBMSE)
  2. Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Publication Date:
Report Number(s):
LLNL-JRNL-741163
Journal ID: ISSN 2056-9890; ACSECI
Grant/Contract Number:
AC52-07NA27344; N0001417WX00049
Type:
Published Article
Journal Name:
Acta Crystallographica. Section E, Crystallographic Communications
Additional Journal Information:
Journal Volume: E74; Journal Issue: 4; Journal ID: ISSN 2056-9890
Publisher:
International Union of Crystallography
Research Org:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Sponsoring Org:
USDOE; US Department of the Navy, Office of Naval Research (ONR)
Country of Publication:
United States
Language:
English
Subject:
75 CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND SUPERFLUIDITY; 37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; crystal structure; tetra­zole; oxa­diazole; tri­amino­guandidinium; hydrazinium; hydroxyl­ammonium; amino­guanidinium; 5-amino-1H-tetra­zol-4-ium; energetic materials
OSTI Identifier:
1437844
Alternate Identifier(s):
OSTI ID: 1438804

Giles, Ian D., DeHope, Alan J., Zuckerman, Nathaniel B., Parrish, Damon A., and Pagoria, Philip F.. Effect of counter-ion on packing and crystal density of 5,5'-(3,3'-bi[1,2,4-oxadiazole]-5,5'-diyl)bis(1 H -tetrazol-1-olate) with five different cations. United States: N. p., Web. doi:10.1107/S205698901800364X.
Giles, Ian D., DeHope, Alan J., Zuckerman, Nathaniel B., Parrish, Damon A., & Pagoria, Philip F.. Effect of counter-ion on packing and crystal density of 5,5'-(3,3'-bi[1,2,4-oxadiazole]-5,5'-diyl)bis(1 H -tetrazol-1-olate) with five different cations. United States. doi:10.1107/S205698901800364X.
Giles, Ian D., DeHope, Alan J., Zuckerman, Nathaniel B., Parrish, Damon A., and Pagoria, Philip F.. 2018. "Effect of counter-ion on packing and crystal density of 5,5'-(3,3'-bi[1,2,4-oxadiazole]-5,5'-diyl)bis(1 H -tetrazol-1-olate) with five different cations". United States. doi:10.1107/S205698901800364X.
@article{osti_1437844,
title = {Effect of counter-ion on packing and crystal density of 5,5'-(3,3'-bi[1,2,4-oxadiazole]-5,5'-diyl)bis(1 H -tetrazol-1-olate) with five different cations},
author = {Giles, Ian D. and DeHope, Alan J. and Zuckerman, Nathaniel B. and Parrish, Damon A. and Pagoria, Philip F.},
abstractNote = {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-oxadiazole]-5,5′-diyl)bis(1 H -tetrazol-1-olate), with the following cations: hydrazinium ( 1 ) (2N 2 H 5 + ·C 6 N 12 O 4 2− ), hydroxylammonium ( 2 ) 2NH 4 O + ·C 6 N 12 O 4 2− [Pagoria et al.. (2017). Chem. Heterocycl. Compd , 53 , 760–778; included for comparison], dimethylammonium ( 3 ) (2C 2 H 8 N + ·C 6 N 12 O 4 2− ), 5-amino-1 H -tetrazol-4-ium ( 4 ) (2CH 4 N 5 + ·C 6 N 12 O 4 2− ·4H 2 O), and aminoguanidinium ( 5 ) (2CH 7 N 4 + ·C 6 N 12 O 4 2− ). Both the supramolecular interactions 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 tetrazolate ring is disordered over two positions [occupancy ratio 0.907 (5):0.093 (5)] due to a 180° rotation in the terminal tetrazole rings.},
doi = {10.1107/S205698901800364X},
journal = {Acta Crystallographica. Section E, Crystallographic Communications},
number = 4,
volume = E74,
place = {United States},
year = {2018},
month = {3}
}

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