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Volume 69 
Part 3 
Page o384  
March 2013  

Received 28 January 2013
Accepted 11 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.083
Data-to-parameter ratio = 12.0
Details
Open access

2-Nitro-1,3-dinitrooxypropane

aMS C920, Los Alamos National Laboratory, Los Alamos, NM 87545, USA,bTechnical Staff Member, MS C920, Los Alamos National Laboratory, Los Alamos, NM 87545, USA, and cCBMSE, Code 6910, Naval Research Laboratory, Washington, DC 20375, USA
Correspondence e-mail: damon.parrish@nrl.navy.mil

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-H...O contacts apparently provide some additional packing stabilization.

Related literature

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[Chavez, D. E., Hiskey, M. A., Naud, D. L. & Parrish, D. A. (2008). Angew. Chem. Int. Ed. 23, 8307-8309.])·The title compound was first synthesized by Römer (1955)[Römer, F. (1955). Angew. Chem. 67, 157.] 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[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.]).

[Scheme 1]

Experimental

Crystal data
  • C3H5N3O8

  • Mr = 211.10

  • Orthorhombic, C m c 21

  • a = 14.046 (5) Å

  • b = 9.607 (5) Å

  • c = 5.903 (3) Å

  • V = 796.5 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 293 K

  • 0.38 × 0.02 × 0.01 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.935, Tmax = 0.998

  • 3416 measured reflections

  • 841 independent reflections

  • 587 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.083

  • S = 1.00

  • 841 reflections

  • 70 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5B...O4i 0.97 2.56 3.405 (5) 145
Symmetry code: (i) [-x+1, -y+1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2008[Bruker (2008). SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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 ).


Acknowledgements

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).

References

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.  [ISI] [CSD] [CrossRef]
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.  [CrossRef] [details]
Römer, F. (1955). Angew. Chem. 67, 157.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o384  [ doi:10.1107/S1600536813004170 ]

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