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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

Journal Article · · Acta Crystallographica. Section E, Crystallographic Communications

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.

Research Organization:
Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)
Sponsoring Organization:
USDOE; US Department of the Navy, Office of Naval Research (ONR)
Grant/Contract Number:
AC52-07NA27344; N0001417WX00049
OSTI ID:
1437844
Alternate ID(s):
OSTI ID: 1438804
Report Number(s):
LLNL-JRNL-741163; ACSECI; PII: S205698901800364X
Journal Information:
Acta Crystallographica. Section E, Crystallographic Communications, Journal Name: Acta Crystallographica. Section E, Crystallographic Communications Vol. 74 Journal Issue: 4; ISSN 2056-9890
Publisher:
International Union of Crystallography (IUCr)Copyright Statement
Country of Publication:
United Kingdom
Language:
English

References (11)

Improved Synthesis and X-Ray Structure of 5-Aminotetrazolium Nitrate journal June 2005
Anion-π interactions journal January 2008
Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials journal June 2017
Crystal Packing of Low-Sensitivity and High-Energy Explosives journal August 2014
A short history of SHELX journal December 2007
The crystal structure of hydroxylammonium perchlorate (NH 3 OH + ClO 4 ) at −150°C journal September 1969
Crystal structure refinement with SHELXL journal January 2015
Aminoguanidinium nitrate journal December 1994
The crystal structure of hydrazinium chloride, N 2 H 5 Cl journal March 1952
The Cambridge Structural Database
  • Groom, Colin R.; Bruno, Ian J.; Lightfoot, Matthew P.
  • Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 2, p. 171-179 https://doi.org/10.1107/S2052520616003954
journal April 2016
Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds journal January 1987