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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

Abstract

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; ; ORCiD logo; ;
Publication Date:
Research Org.:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Sponsoring Org.:
USDOE; US Department of the Navy, Office of Naval Research (ONR)
OSTI Identifier:
1437844
Alternate Identifier(s):
OSTI ID: 1438804
Report Number(s):
LLNL-JRNL-741163
Journal ID: ISSN 2056-9890; ACSECI; PII: S205698901800364X
Grant/Contract Number:  
AC52-07NA27344; N0001417WX00049
Resource Type:
Published Article
Journal Name:
Acta Crystallographica. Section E, Crystallographic Communications
Additional Journal Information:
Journal Name: Acta Crystallographica. Section E, Crystallographic Communications Journal Volume: 74 Journal Issue: 4; Journal ID: ISSN 2056-9890
Publisher:
International Union of Crystallography (IUCr)
Country of Publication:
United Kingdom
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

Citation Formats

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 Kingdom: N. p., 2018. 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 Kingdom. doi:10.1107/S205698901800364X.
Giles, Ian D., DeHope, Alan J., Zuckerman, Nathaniel B., Parrish, Damon A., and Pagoria, Philip F. Fri . "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 Kingdom. 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 = 74,
place = {United Kingdom},
year = {2018},
month = {3}
}

Journal Article:
Free Publicly Available Full Text
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DOI: 10.1107/S205698901800364X

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Works referenced in this record:

Improved Synthesis and X-Ray Structure of 5-Aminotetrazolium Nitrate
journal, June 2005

  • von Denffer, Moritz; Klapötke, Thomas M.; Kramer, Gernot
  • Propellants, Explosives, Pyrotechnics, Vol. 30, Issue 3
  • DOI: 10.1002/prep.200500004

Anion-π interactions
journal, January 2008

  • Schottel, Brandi L.; Chifotides, Helen T.; Dunbar, Kim R.
  • Chem. Soc. Rev., Vol. 37, Issue 1
  • DOI: 10.1039/B614208G

Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials
journal, June 2017

  • Pagoria, Philip F.; Zhang, Mao-Xi; Zuckerman, Nathaniel B.
  • Chemistry of Heterocyclic Compounds, Vol. 53, Issue 6-7
  • DOI: 10.1007/s10593-017-2122-9

Crystal Packing of Low-Sensitivity and High-Energy Explosives
journal, August 2014

  • Ma, Yu; Zhang, Anbang; Zhang, Chenghua
  • Crystal Growth & Design, Vol. 14, Issue 9
  • DOI: 10.1021/cg501048v

A short history of SHELX
journal, December 2007

  • Sheldrick, George M.
  • Acta Crystallographica Section A Foundations of Crystallography, Vol. 64, Issue 1, p. 112-122
  • DOI: 10.1107/S0108767307043930

The crystal structure of hydroxylammonium perchlorate (NH 3 OH + ClO 4 ) at −150°C
journal, September 1969

  • Dickens, B.
  • Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 25, Issue 9
  • DOI: 10.1107/S0567740869004869

Crystal structure refinement with SHELXL
journal, January 2015

  • Sheldrick, George M.
  • Acta Crystallographica Section C Structural Chemistry, Vol. 71, Issue 1, p. 3-8
  • DOI: 10.1107/S2053229614024218

Aminoguanidinium nitrate
journal, December 1994

  • Akella, A.; Keszler, D. A.
  • Acta Crystallographica Section C Crystal Structure Communications, Vol. 50, Issue 12
  • DOI: 10.1107/S0108270194007730

The crystal structure of hydrazinium chloride, N 2 H 5 Cl
journal, March 1952


The Cambridge Structural Database
journal, April 2016

  • 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
  • DOI: 10.1107/S2052520616003954

Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds
journal, January 1987

  • Allen, Frank H.; Kennard, Olga; Watson, David G.
  • Journal of the Chemical Society, Perkin Transactions 2, Issue 12
  • DOI: 10.1039/p298700000s1