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

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 · Thu Mar 08 23:00:00 EST 2018 · Acta Crystallographica. Section E, Crystallographic Communications

DOI:https://doi.org/10.1107/S205698901800364X· OSTI ID:1437844

; DeHope, Alan J.; ; Parrish, Damon A.; Pagoria, Philip F.

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.

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC52-07NA27344

OSTI ID:: 1437844

Alternate ID(s):: OSTI ID: 1438804

Journal Information:: Acta Crystallographica. Section E, Crystallographic Communications, Journal Name: Acta Crystallographica. Section E, Crystallographic Communications Journal Issue: 4 Vol. 74; ISSN ACSECI; 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 von Denffer, Moritz; Klapötke, Thomas M.; Kramer, Gernot Propellants, Explosives, Pyrotechnics, Vol. 30, Issue 3 https://doi.org/10.1002/prep.200500004	journal	June 2005
Synthesis and characterization of multicyclic oxadiazoles and 1-hydroxytetrazoles as energetic materials Pagoria, Philip F.; Zhang, Mao-Xi; Zuckerman, Nathaniel B. Chemistry of Heterocyclic Compounds, Vol. 53, Issue 6-7 https://doi.org/10.1007/s10593-017-2122-9	journal	June 2017
Crystal Packing of Low-Sensitivity and High-Energy Explosives Ma, Yu; Zhang, Anbang; Zhang, Chenghua Crystal Growth & Design, Vol. 14, Issue 9 https://doi.org/10.1021/cg501048v	journal	August 2014
Anion-π interactions Schottel, Brandi L.; Chifotides, Helen T.; Dunbar, Kim R. Chem. Soc. Rev., Vol. 37, Issue 1 https://doi.org/10.1039/B614208G	journal	January 2008
Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds Allen, Frank H.; Kennard, Olga; Watson, David G. Journal of the Chemical Society, Perkin Transactions 2, Issue 12 https://doi.org/10.1039/p298700000s1	journal	January 1987
Aminoguanidinium nitrate Akella, A.; Keszler, D. A. Acta Crystallographica Section C Crystal Structure Communications, Vol. 50, Issue 12 https://doi.org/10.1107/S0108270194007730	journal	December 1994
A short history of SHELX Sheldrick, George M. Acta Crystallographica Section A Foundations of Crystallography, Vol. 64, Issue 1, p. 112-122 https://doi.org/10.1107/S0108767307043930	journal	December 2007
The crystal structure of hydrazinium chloride, N ₂ H ₅ Cl Sakurai, K.; Tomiie, Y. Acta Crystallographica, Vol. 5, Issue 2 https://doi.org/10.1107/S0365110X5200085X	journal	March 1952
The crystal structure of hydroxylammonium perchlorate (NH ₃ OH ⁺ ClO ₄ ⁻ ) at −150°C Dickens, B. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 25, Issue 9 https://doi.org/10.1107/S0567740869004869	journal	September 1969
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
Crystal structure refinement with SHELXL Sheldrick, George M. Acta Crystallographica Section C Structural Chemistry, Vol. 71, Issue 1, p. 3-8 https://doi.org/10.1107/S2053229614024218	journal	January 2015

Similar Records

Synthesis and crystal structures of 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde)

Journal Article · Wed Nov 21 23:00:00 EST 2018 · Acta Crystallographica. Section E, Crystallographic Communications · OSTI ID:1630006

[(eta5-PentamethylcyclopentadienylYb(III)(5,5'-dimethyl-2,2-bipyridyl)mu-OH)2(mu 2-trifluoromethylsulfanato-O,O')][tetraphenylborate](5,5'-dimethyl-2,2-bipyridyl)

Journal Article · Tue Jan 22 23:00:00 EST 2008 · Acta Crystallographica Volume E · OSTI ID:929506

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

Citation Formats

References (11)

Similar Records

Related Subjects