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

Giles, Ian D.; DeHope, Alan J.; Zuckerman, Nathaniel B.; Parrish, Damon A.; Pagoria, Philip F.

doi:10.1107/S205698901800364X

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 »« less

Authors:

; DeHope, Alan J.;

; Parrish, Damon A.; Pagoria, Philip F.

Publication Date:: Fri Mar 09 00:00:00 EST 2018

Research Org.:: Lawrence Livermore National Laboratory (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.

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                    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.  https://doi.org/10.1107/S205698901800364X

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                    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.  https://doi.org/10.1107/S205698901800364X.

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@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         = {Fri Mar 09 00:00:00 EST 2018},

  month        = {Fri Mar 09 00:00:00 EST 2018}

}

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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

Sakurai, K.; Tomiie, Y.
Acta Crystallographica, Vol. 5, Issue 2
DOI: 10.1107/S0365110X5200085X

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

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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

Citation Formats

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

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Aminoguanidinium nitrate journal, December 1994

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The Cambridge Structural Database journal, April 2016

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

Improved Synthesis and X-Ray Structure of 5-Aminotetrazolium Nitrate
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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
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Crystal structure refinement with SHELXL
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Aminoguanidinium nitrate
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The crystal structure of hydrazinium chloride, N ₂ H ₅ Cl
journal, March 1952

The Cambridge Structural Database
journal, April 2016

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