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Title: Crystal structure of 2-azido-1 H -imidazole-4,5-dicarbonitrile

Abstract

We report that in the title compound, C 5HN 7, the nitrile and azido substituents are close to being coplanar with the central ring. Molecules in the crystal are linked via an N—H...N hydrogen bond to a nitrile acceptor, forming a chain extending along the c-axis direction.

Authors:
 [1];  [1];  [1];  [1]
  1. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Publication Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE National Nuclear Security Administration (NNSA)
OSTI Identifier:
1254852
Alternate Identifier(s):
OSTI ID: 1321758
Report Number(s):
LA-UR-15-23927; LA-UR-15-23325
Journal ID: ISSN 2056-9890; ACSECI; PII: S2056989015013444
Grant/Contract Number:  
AC52-06NA25396
Resource Type:
Accepted Manuscript
Journal Name:
Acta Crystallographica. Section E, Crystallographic Communications
Additional Journal Information:
Journal Volume: 71; Journal Issue: 9; 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; organic chemistry; hydrogen bonding; 2-azido-4,5-dicyano-1H-imidazole; 36 MATERIALS SCIENCE; imidazole; crystal structure; 2-azido-4,5-di­cyano-1H-imidazole

Citation Formats

Windler, G. Kenneth, Scott, Brian L., Tomson, Neil C., and Leonard, Philip W. Crystal structure of 2-azido-1 H -imidazole-4,5-dicarbonitrile. United States: N. p., 2015. Web. doi:10.1107/S2056989015013444.
Windler, G. Kenneth, Scott, Brian L., Tomson, Neil C., & Leonard, Philip W. Crystal structure of 2-azido-1 H -imidazole-4,5-dicarbonitrile. United States. doi:10.1107/S2056989015013444.
Windler, G. Kenneth, Scott, Brian L., Tomson, Neil C., and Leonard, Philip W. Thu . "Crystal structure of 2-azido-1 H -imidazole-4,5-dicarbonitrile". United States. doi:10.1107/S2056989015013444. https://www.osti.gov/servlets/purl/1254852.
@article{osti_1254852,
title = {Crystal structure of 2-azido-1 H -imidazole-4,5-dicarbonitrile},
author = {Windler, G. Kenneth and Scott, Brian L. and Tomson, Neil C. and Leonard, Philip W.},
abstractNote = {We report that in the title compound, C5HN7, the nitrile and azido substituents are close to being coplanar with the central ring. Molecules in the crystal are linked via an N—H...N hydrogen bond to a nitrile acceptor, forming a chain extending along the c-axis direction.},
doi = {10.1107/S2056989015013444},
journal = {Acta Crystallographica. Section E, Crystallographic Communications},
number = 9,
volume = 71,
place = {United States},
year = {2015},
month = {8}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Figures / Tables:

Table 1 Table 1: Hydrogen-bond geometry (Å, °).

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Works referenced in this record:

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journal, March 2008

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    Works referencing / citing this record:

    CCDC 1412579: Experimental Crystal Structure Determination: RUSBUE : 2-azido-1H-imidazole-4,5-dicarbonitrile
    dataset, July 2015

    • Windler, G.; Scott, B.; Tomson, N.
    • Cambridge Structural Database (CSD)
    • DOI: 10.5517/cc1jdx2x

    In Search of Ionic Liquids Incorporating Azolate Anions
    journal, June 2006

    • Katritzky, Alan R.; Singh, Shailendra; Kirichenko, Kostyantyn
    • Chemistry - A European Journal, Vol. 12, Issue 17
    • DOI: 10.1002/chem.200500840

    Hydrogen cyanide chemistry. V. Diazodicyanoimidazole and dicyanoimidazole halonium ylides
    journal, April 1973

    • Sheppard, W. A.; Webster, O. W.
    • Journal of the American Chemical Society, Vol. 95, Issue 8
    • DOI: 10.1021/ja00789a054

    Synthesis of nitrogen-rich imidazole, 1,2,4-triazole and tetrazole-based compounds
    journal, January 2014

    • Srinivas, Dharavath; Ghule, Vikas D.; Muralidharan, Krishnamurthi
    • RSC Advances, Vol. 4, Issue 14
    • DOI: 10.1039/c3ra47227b

    Crystal structure of 4,5-dinitro-1 H -imidazole
    journal, August 2015

    • Windler, G. Kenneth; Scott, Brian L.; Tomson, Neil C.
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 71, Issue 9
    • DOI: 10.1107/s2056989015013432

      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.