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Structures of dinitroazetidine and three of its carbonyl derivatives

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Abstract

The structures of DNAZ (3,3-dinitroazetidine), DNAZ-COH, DNAZ-CO-DNAZ, and (DNAZ-CO)2 have been determined. DNAZ crystallizes in the space group P21/c with cell parameters a = 5.928(7) Å, b = 15.8380(2) Å, c = 12.6837(15) and β = 93.23°. DNAZ-COH crystallizes in the space group P21/c with cell parameters a = 10.3270(10) Å, b = 6.0615(12) Å, c = 11.2514(12), and β = 100.17°. DNAZ-CO-DNAZ crystallizes in the space group P21/n with cell parameters a = 10.3630(6) Å, b = 6.0901(5) Å, c = 19.9421(11) and β = 102.74°. (DNAZ-CO)2 crystallizes in the orthorhombic space group Fdd2 with cell parameters a = 13.1956(10) Å, b = 19.524(3) Å, c = 10.3259(11). This last compound is unique in that the trans carbonyls are planar and the adjoining azetidine rings are also planar to within 0.1° in all torsion angles. DNAZ crystals have a dimeric asymmetric unit where two nonequal molecules are bonded to each other with a single hydrogen bond. Like other four-membered rings with gem-dinitro groups, most of these dinitroazetidines display mutually perpendicular nitro groups.

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Author notes

  1. Suhithi M. Peiris & T.P. Russell

    Present address: Chemistry and Detonics Division, Building 600, USA

Authors and Affiliations

  1. Code 6112, Naval Research Lab, 4555 Overlook Ave. SW., Washington, DC, 20375;

    Suhithi M. Peiris & T.P. Russell

  2. Code 920, Naval Surface Warfare Center—Indian Head, 101 Strauss Ave., Indian Head, Maryland, 20640

    Suhithi M. Peiris & T.P. Russell

  3. Laboratory for the Structure of Matter, Code 6030, Naval Research Laboratory, Washington, DC, 20375

    Richard Gilardi

  4. Geo-Centers, Inc., ARDEC, Building 3028, Picatinny Arsenal, New Jersey 07806

    Paritosh R. Dave

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  1. Suhithi M. Peiris
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  3. Paritosh R. Dave
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  4. T.P. Russell
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Peiris, S.M., Gilardi, R., Dave, P.R. et al. Structures of dinitroazetidine and three of its carbonyl derivatives. Journal of Chemical Crystallography 30, 647–653 (2000). https://doi.org/10.1023/A:1011996132020

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