[Journal logo]

Volume 68 
Part 8 
Page o2440  
August 2012  

Received 22 June 2012
Accepted 5 July 2012
Online 14 July 2012

[bt5956sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](O-N) = 0.009 Å
Disorder in main residue
R = 0.039
wR = 0.126
Data-to-parameter ratio = 6.0
Details
Open access

1,3-Dinitrosoimidazolidine

Augusto Rivera,a* Diego Quiroga,a Jaime Ríos-Motta,a Michal Dusekb and Karla Fejfarováb

aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia, and bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

The title compound, C3H6N4O2, exhibits partial disorder with the refined occupancy ratios of the two components being 0.582 (5):0.418 (5). In the major component, the nitroso groups have a relative syn spatial arrangement [O=N...N=O pseudo-torsion angle = 1.1 (4)°], whereas the other component has an anti disposition [177.6 (1)°]. The N-N=O moieties are almost coplanar with a dihedral angle of 5.3 (3)°, while in the minor occupied set of atoms, this angle is 8 (1)°. In both components, the imidazolidine ring adopts a twisted conformation on the C-C bond and the crystal structure shows the strain of this ring according to the N-CH2-CH2-N torsion angles [25.9 (5) and -23.8 (7)°]. In the crystal, molecules are linked by weak C-H...O hydrogen bonds.

Related literature

For a related structure, see: Rivera et al. (2011[Rivera, A., Quiroga, D., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2011). Acta Cryst. C67, o505-o508.]). For the synthesis of the title compound, see: Rivera et al. (1997[Rivera, A., Gallo, G. I. & Joseph-Nathan, P. (1997). Synth. Commun. 27, 163-168.]). For ring conformations, see Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For chemical background on the synthesis and uses of N-nitroso amines, see: Di Salvo et al. (2008[Di Salvo, F., Estrin, D. A., Leitus, G. & Doctorovich, F. (2008). Organometallics, 27, 1985-1995.]).

[Scheme 1]

Experimental

Crystal data

  • C3H6N4O2

  • Mr = 130.1

  • Orthorhombic, P n a 21

  • a = 9.5154 (2) Å

  • b = 5.4338 (1) Å

  • c = 10.7104 (2) Å

  • V = 553.78 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.14 mm-1

  • T = 120 K

  • 0.39 × 0.20 × 0.14 mm
Data collection

  • Agilent Xcalibur diffractometer with an Atlas (Gemini Ultra Cu) detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.636, Tmax = 1

  • 5160 measured reflections

  • 522 independent reflections

  • 514 reflections with I > 3[sigma](I)

  • Rint = 0.031
Refinement

  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.126

  • S = 2.86

  • 522 reflections

  • 87 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3y-H3ya...O1yi 0.96 1.85 2.681 (12) 143
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: JANA2006.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5956 ).

Acknowledgements

The authors acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia for financial support of this work (grant No. 13066) and the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences of the Czech Republic. DQ acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Di Salvo, F., Estrin, D. A., Leitus, G. & Doctorovich, F. (2008). Organometallics, 27, 1985-1995.  [CSD] [CrossRef] [ChemPort]
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Rivera, A., Gallo, G. I. & Joseph-Nathan, P. (1997). Synth. Commun. 27, 163-168.  [CrossRef] [ChemPort] [ISI]
Rivera, A., Quiroga, D., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2011). Acta Cryst. C67, o505-o508.  [CSD] [CrossRef] [details]

Acta Cryst (2012). E68, o2440  [ doi:10.1107/S1600536812030796 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.