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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

In the mol­ecule of neutral bis­[(1H-tetra­zol-5-yl)meth­yl]nitramide, (I), C 4H 6N 10O 2, 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), CH 9N 6 +·C 4H 5N 10O 2 -, 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), 2NH 4 +·C 4H 4N 10O 2 2-·H 2O, 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 sp 2-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:
 [1] ;  [1] ;  [1] ;  [1] ;  [2] ;  [2]
  1. Naval Research Lab. (NRL), Washington, DC (United States). Center for Biomolecular Science and Engineering
  2. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Publication Date:
Report Number(s):
LA-UR-18-21294
Journal ID: ISSN 2056-9890
Grant/Contract Number:
AC52-06NA25396; N00014–15-WX-0–0149
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
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
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; crystal structure; tetrazole; triaminoguandidinium; nitramide; energetic
OSTI Identifier:
1463495

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., 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. doi:10.1107/S2056989017008817.
Mitchell, Lauren A., Imler, Gregory H., Parrish, Damon A., Deschamps, Jeffrey R., Leonard, Philip W., and Chavez, David E.. 2017. "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. doi: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 = {2017},
month = {6}
}