Received 28 January 2013
The title compound, C3H5N3O8, was synthesized by reacting 2-nitropropane-1,3-diol with acetyl nitrate. The molecule is bisected by a crystallograpic mirror plane. In the crystal, the molecules pack in a ribbon-like fashion along the c axis, with the central nitro groups pointing in the same direction. C-HO contacts apparently provide some additional packing stabilization.
Nitrate esters are often studied for their energetic materials properties. For example, we have reported the synthesis and crystal structure of a low melting nitrate ester (Chavez, et al. 2008)·The title compound was first synthesized by Römer (1955) but no information has been reported on the crystal structure of this material. A smilar structure was reported that differs only in a nitrooxy group at the 2-position (Espenbetov et al. 1984).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2094 ).
The authors would like to thank the DoD/DOE Joint Munitions Technology Development Program. Los Alamos National Laboratory is operated by Los Alamos National Security (LANS, LLC) under contract No. DE-AC52-06 N A25396 for the US Department of Energy. Crystallographic studies were supported in part by the Office of Naval Research (ONR) and the Naval Research Laboratory (NRL).
Bruker (2008). SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chavez, D. E., Hiskey, M. A., Naud, D. L. & Parrish, D. A. (2008). Angew. Chem. Int. Ed. 23, 8307-8309.
Espenbetov, A. A., Antipin, M. Yu., Struchkov, Yu. T., Philippov, V. A., Tsirel'son, V. G., Ozerov, R. P. & Svetlov, B. S. (1984). Acta Cryst. C40, 2096-2098.
Römer, F. (1955). Angew. Chem. 67, 157.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.