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Volume 69 
Part 8 
Page o1241  
August 2013  

Received 13 May 2013
Accepted 8 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 105 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.090
Data-to-parameter ratio = 14.5
Details
Open access

1,4-Bis(2-diazoacetyl)piperazine

aDepartment of Chemistry, University of Oslo, PO Box 1033 Blindern, N-0315 Oslo, Norway
Correspondence e-mail: c.h.gorbitz@kjemi.uio.no

The asymmetric unit of the title compound, C8H10N6O2, contains one-half molecule, which is completed by a crystallographic center of symmetry. The piperazine ring adopts a chair conformation. In the crystal, weak C-H...O interactions link the molecules into layers parallel to the bc plane. The crystal packing also exhibits short N...N contacts of 3.0467 (16) Å between the terminal diazo N atoms from neighbouring molecules.

Related literature

For related structures in the Cambridge Structural Database (Version 5.34 of November 2012; Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]), see: Kaupang (2010[Kaupang, Å. (2010). MSc Thesis, University of Oslo, Norway, 230 pp., PDF available online at http://urn.nb.no/URN:NBN:no-26202 or through http://www.duo.uio.no/ .]); Kaupang et al. (2010[Kaupang, Å., Görbitz, C. H. & Hansen, T. (2010). Acta Cryst. E66, o1299.], 2011[Kaupang, Å., Görbitz, C. H. & Hansen, T. (2011). Acta Cryst. E67, o1844-o1845.]); Aliev et al. (1980[Aliev, Z. G., Kartsev, V. G., Atovmyan, L. O. & Bogdanov, G. N. (1980). Khim. Farm. Zh. 14, 84-88.]); Fitzgerald & Jensen (1978[Fitzgerald, A. & Jensen, L. H. (1978). Acta Cryst. B34, 828-836.]); Hope & Black (1972[Hope, H. & Black, K. T. (1972). Acta Cryst. B28, 3632-3634.]). For normal bond lengths in organic compounds, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-17.]). For synthetic details, see: Kaupang & Bonge-Hansen (2013[Kaupang, Å. & Bonge-Hansen, T. (2013). Beil. J. Org. Chem. Submitted.]); Kaupang (2010[Kaupang, Å. (2010). MSc Thesis, University of Oslo, Norway, 230 pp., PDF available online at http://urn.nb.no/URN:NBN:no-26202 or through http://www.duo.uio.no/ .]); Toma et al. (2007[Toma, T., Shimokawa, J. & Fukuyama, T. (2007). Org. Lett. 9, 3195-3197.]). For the synthesis of other diazoacetamides with a 1,4-diaza six-membered ring, see: Kaupang (2010[Kaupang, Å. (2010). MSc Thesis, University of Oslo, Norway, 230 pp., PDF available online at http://urn.nb.no/URN:NBN:no-26202 or through http://www.duo.uio.no/ .]); Mickelson et al. (1996[Mickelson, J. W., Jacobsen, E. J., Carter, D. B., Im, H. K., Im, W. B., Schreur, P. J. K. D., Sethy, V. H., Tang, A. H., McGee, J. E. & Petke, J. D. (1996). J. Med. Chem. 39, 4654-4666.]). For the synthesis of other diazoacetamides, see: Ouihia et al. (1993[Ouihia, A., Rene, L., Guilhem, J., Pascard, C. & Badet, B. (1993). J. Org. Chem. 58, 1641-1642.]). For the Chemical Abstracts Service, see: American Chemical Society (2008[American Chemical Society (2008). Chemical Abstracts Service, American Chemical Society, Columbus, OH, USA; accessed Apr 27, 2010.]). For graph-set notation for hydrogen-bonding patterns, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10N6O2

  • Mr = 222.22

  • Monoclinic, P 21 /c

  • a = 4.0630 (7) Å

  • b = 9.0941 (15) Å

  • c = 13.230 (2) Å

  • [beta] = 94.453 (2)°

  • V = 487.38 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 105 K

  • 1.4 × 0.2 × 0.2 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.859, Tmax = 0.977

  • 4255 measured reflections

  • 1190 independent reflections

  • 1013 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.090

  • S = 1.04

  • 1190 reflections

  • 82 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H21...O1i 0.92 (1) 2.39 (1) 3.2219 (15) 151 (1)
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: CV5412 ).


References

Aliev, Z. G., Kartsev, V. G., Atovmyan, L. O. & Bogdanov, G. N. (1980). Khim. Farm. Zh. 14, 84-88.  [ChemPort]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-17.
American Chemical Society (2008). Chemical Abstracts Service, American Chemical Society, Columbus, OH, USA; accessed Apr 27, 2010.
Bruker (2007). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [Web of Science] [IUCr Journals]
Fitzgerald, A. & Jensen, L. H. (1978). Acta Cryst. B34, 828-836.  [CrossRef] [IUCr Journals]
Hope, H. & Black, K. T. (1972). Acta Cryst. B28, 3632-3634.  [CrossRef] [ChemPort] [IUCr Journals]
Kaupang, Å. (2010). MSc Thesis, University of Oslo, Norway, 230 pp., PDF available online at http://urn.nb.no/URN:NBN:no-26202 or through http://www.duo.uio.no/ .
Kaupang, Å. & Bonge-Hansen, T. (2013). Beil. J. Org. Chem. Submitted.
Kaupang, Å., Görbitz, C. H. & Hansen, T. (2010). Acta Cryst. E66, o1299.  [CSD] [CrossRef] [IUCr Journals]
Kaupang, Å., Görbitz, C. H. & Hansen, T. (2011). Acta Cryst. E67, o1844-o1845.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Mickelson, J. W., Jacobsen, E. J., Carter, D. B., Im, H. K., Im, W. B., Schreur, P. J. K. D., Sethy, V. H., Tang, A. H., McGee, J. E. & Petke, J. D. (1996). J. Med. Chem. 39, 4654-4666.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Ouihia, A., Rene, L., Guilhem, J., Pascard, C. & Badet, B. (1993). J. Org. Chem. 58, 1641-1642.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Toma, T., Shimokawa, J. & Fukuyama, T. (2007). Org. Lett. 9, 3195-3197.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1241  [ doi:10.1107/S1600536813018801 ]

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