Crystal structures of the three closely related compounds: bis[(1H-tetrazol-5-yl)methyl]nitramide, triaminoguanidinium 5-({[(1H-tetrazol-5-yl)methyl](nitro)amino}methyl)tetrazol-1-ide, and diammonium bis[(tetrazol-1-id-5-yl)methyl]nitramide monohydrate
Abstract
In the molecule of neutral bis[(1H-tetrazol-5-yl)methyl]nitramide, (I), C4H6N10O2, there are two intramolecular N—H∙∙∙O hydrogen bonds. In the crystal, N—H∙∙∙N hydrogen bonds link molecules, forming a two-dimensional network parallel to (-201) and weak C—H∙∙∙O, C—H∙∙∙N hydrogen bonds, and intermolecular π–π stacking completes the three-dimensional network. The anion in the molecular salt, triaminoguanidinium 5-({[(1H-tetrazol-5-yl)methyl](nitro)amino}methyl)tetrazol-1-ide, (II), CH9N6+·C4H5N10O2-, displays intramolecular π–π stacking and in the crystal, N—H∙∙∙N and N—H∙∙∙O hydrogen bonds link the components of the structure, forming a three-dimensional network. In the crystal of diammonium bis[(tetrazol-1-id-5-yl)methyl]nitramide monohydrate, (III), 2NH4+·C4H4N10O22-·H2O, O—H∙∙∙N, N—H∙∙∙N, and N—H∙∙∙O hydrogen bonds link the components of the structure into a three-dimensional network. In addition, there is intermolecular π–π stacking. In all three structures, the central N atom of the nitramide is mainly sp2-hybridized. Bond lengths indicate delocalization of charges on the tetrazole rings for all three compounds. Compound (II) was found to be a non-merohedral twin and was solved and refined in the major component.
- Authors:
-
- Naval Research Lab. (NRL), Washington, DC (United States). Center for Biomolecular Science and Engineering
- Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
- Publication Date:
- Research Org.:
- Los Alamos National Lab. (LANL), Los Alamos, NM (United States); Naval Research Lab. (NRL), Washington, DC (United States)
- Sponsoring Org.:
- USDOE; Office of Naval Research (ONR) (United States); American Society for Engineering Education (ASEE); USDOD
- OSTI Identifier:
- 1463495
- Report Number(s):
- LA-UR-18-21294
Journal ID: ISSN 2056-9890
- Grant/Contract Number:
- AC52-06NA25396; N00014–15-WX-0–0149
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Acta Crystallographica. Section E, Crystallographic Communications
- Additional Journal Information:
- Journal Volume: 73; Journal Issue: 7; Journal ID: ISSN 2056-9890
- Publisher:
- International Union of Crystallography
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; crystal structure; tetrazole; triaminoguandidinium; nitramide; energetic
Citation Formats
Mitchell, Lauren A., Imler, Gregory H., Parrish, Damon A., Deschamps, Jeffrey R., Leonard, Philip W., and Chavez, David E. Crystal structures of the three closely related compounds: bis[(1H-tetrazol-5-yl)methyl]nitramide, triaminoguanidinium 5-({[(1H-tetrazol-5-yl)methyl](nitro)amino}methyl)tetrazol-1-ide, and diammonium bis[(tetrazol-1-id-5-yl)methyl]nitramide monohydrate. United States: N. p., 2017.
Web. doi:10.1107/S2056989017008817.
Mitchell, Lauren A., Imler, Gregory H., Parrish, Damon A., Deschamps, Jeffrey R., Leonard, Philip W., & Chavez, David E. Crystal structures of the three closely related compounds: bis[(1H-tetrazol-5-yl)methyl]nitramide, triaminoguanidinium 5-({[(1H-tetrazol-5-yl)methyl](nitro)amino}methyl)tetrazol-1-ide, and diammonium bis[(tetrazol-1-id-5-yl)methyl]nitramide monohydrate. United States. https://doi.org/10.1107/S2056989017008817
Mitchell, Lauren A., Imler, Gregory H., Parrish, Damon A., Deschamps, Jeffrey R., Leonard, Philip W., and Chavez, David E. Tue .
"Crystal structures of the three closely related compounds: bis[(1H-tetrazol-5-yl)methyl]nitramide, triaminoguanidinium 5-({[(1H-tetrazol-5-yl)methyl](nitro)amino}methyl)tetrazol-1-ide, and diammonium bis[(tetrazol-1-id-5-yl)methyl]nitramide monohydrate". United States. https://doi.org/10.1107/S2056989017008817. https://www.osti.gov/servlets/purl/1463495.
@article{osti_1463495,
title = {Crystal structures of the three closely related compounds: bis[(1H-tetrazol-5-yl)methyl]nitramide, triaminoguanidinium 5-({[(1H-tetrazol-5-yl)methyl](nitro)amino}methyl)tetrazol-1-ide, and diammonium bis[(tetrazol-1-id-5-yl)methyl]nitramide monohydrate},
author = {Mitchell, Lauren A. and Imler, Gregory H. and Parrish, Damon A. and Deschamps, Jeffrey R. and Leonard, Philip W. and Chavez, David E.},
abstractNote = {In the molecule of neutral bis[(1H-tetrazol-5-yl)methyl]nitramide, (I), C4H6N10O2, there are two intramolecular N—H∙∙∙O hydrogen bonds. In the crystal, N—H∙∙∙N hydrogen bonds link molecules, forming a two-dimensional network parallel to (-201) and weak C—H∙∙∙O, C—H∙∙∙N hydrogen bonds, and intermolecular π–π stacking completes the three-dimensional network. The anion in the molecular salt, triaminoguanidinium 5-({[(1H-tetrazol-5-yl)methyl](nitro)amino}methyl)tetrazol-1-ide, (II), CH9N6+·C4H5N10O2-, displays intramolecular π–π stacking and in the crystal, N—H∙∙∙N and N—H∙∙∙O hydrogen bonds link the components of the structure, forming a three-dimensional network. In the crystal of diammonium bis[(tetrazol-1-id-5-yl)methyl]nitramide monohydrate, (III), 2NH4+·C4H4N10O22-·H2O, O—H∙∙∙N, N—H∙∙∙N, and N—H∙∙∙O hydrogen bonds link the components of the structure into a three-dimensional network. In addition, there is intermolecular π–π stacking. In all three structures, the central N atom of the nitramide is mainly sp2-hybridized. Bond lengths indicate delocalization of charges on the tetrazole rings for all three compounds. Compound (II) was found to be a non-merohedral twin and was solved and refined in the major component.},
doi = {10.1107/S2056989017008817},
journal = {Acta Crystallographica. Section E, Crystallographic Communications},
number = 7,
volume = 73,
place = {United States},
year = {Tue Jun 20 00:00:00 EDT 2017},
month = {Tue Jun 20 00:00:00 EDT 2017}
}
Works referenced in this record:
Correlation of the hydrogen-bond acceptor properties of nitrogen with the geometry of the N sp 2 →N sp 3 transition in R 1 ( X =)C–N R 2 R 3 substructures: reaction pathway for the protonation of nitrogen
journal, December 1995
- Allen, F. H.; Bird, C. M.; Rowland, R. S.
- Acta Crystallographica Section B Structural Science, Vol. 51, Issue 6
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
WinGX and ORTEP for Windows : an update
journal, July 2012
- Farrugia, Louis J.
- Journal of Applied Crystallography, Vol. 45, Issue 4
A DFT theoretical study of heats of formation and detonation properties of nitrogen-rich explosives
journal, April 2010
- Jaidann, Mounir; Roy, Sandra; Abou-Rachid, Hakima
- Journal of Hazardous Materials, Vol. 176, Issue 1-3
Simple, Nitrogen-Rich, Energetic Salts of 5-Nitrotetrazole
journal, June 2008
- Klapötke, Thomas M.; Mayer, Peter; Miró Sabaté, Carles
- Inorganic Chemistry, Vol. 47, Issue 13
Neutral 5-nitrotetrazoles: easy initiation with low pollution
journal, January 2009
- Klapötke, Thomas M.; Sabaté, Carles Miró; Stierstorfer, Jörg
- New J. Chem., Vol. 33, Issue 1
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
Crystal structure refinement with SHELXL
journal, January 2015
- Sheldrick, George M.
- Acta Crystallographica Section C Structural Chemistry, Vol. 71, Issue 1, p. 3-8
Environmentally compatible next generation green energetic materials (GEMs)
journal, January 2009
- Talawar, M. B.; Sivabalan, R.; Mukundan, T.
- Journal of Hazardous Materials, Vol. 161, Issue 2-3
Energetic Salts Based on Furazan-Functionalized Tetrazoles: Routes to Boost Energy
journal, April 2015
- Wei, Hao; Zhang, Jiaheng; He, Chunlin
- Chemistry - A European Journal, Vol. 21, Issue 23
publCIF : software for editing, validating and formatting crystallographic information files
journal, June 2010
- Westrip, Simon P.
- Journal of Applied Crystallography, Vol. 43, Issue 4
A new design strategy for high-energy low-sensitivity explosives: combining oxygen balance equal to zero, a combination of nitro and amino groups, and N-oxide in one molecule of 1-amino-5-nitrotetrazole-3N-oxide
journal, January 2014
- Wu, Qiong; Zhu, Weihua; Xiao, Heming
- Journal of Materials Chemistry A, Vol. 2, Issue 32
Importance of the consideration of anharmonic motion in charge-density studies: a comparison of variable-temperature studies on two explosives, RDX and HMX
journal, January 2011
- Zhurov, Vladimir V.; Zhurova, Elizabeth A.; Stash, Adam I.
- Acta Crystallographica Section A Foundations of Crystallography, Vol. 67, Issue 2