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Volume 68 
Part 12 
Page o3347  
December 2012  

Received 14 October 2012
Accepted 8 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.130
Data-to-parameter ratio = 13.7
Details
Open access

(E)-tert-Butyl 4-(N'-hydroxycarbamimidoyl)piperazine-1-carboxylate

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Chemistry, U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India, and cDepartment of Studies and Research in Physics, U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C10H20N4O3, the piperazine ring adopts a chair conformation. The molecule adopts an E conformation across the C=N double bond, with the -OH group and the piperazine ring trans to one another. Further, the H atom of the hydroxy group is directed away from the NH2 group. An intramolecular N-H...O contact occurs involving the NH2 group and the oxime O atom. In the crystal, molecules are linked via strong N-H...O and O-H...N hydrogen bonds with alternating R22(6) and C(9) motifs into tetrameric units forming R44(28) motifs.

Related literature

For the synthesis, characterization and biological activity of piperazine and its derivatives, see: Gan et al. (2009a[Gan, L. L., Cai, J. L. & Zhou, C. H. (2009a). Chin. Pharm. J. 44, 1361-1368.],b[Gan, L. L., Lu, Y. H. & Zhou, C. H. (2009b). Chin. J. Biochem. Pharm. 30, 127-131.]); Willems & Ilzerman (2010[Willems, L. I. & Ilzerman, A. P. (2010). Med. Chem. Res. 30, 778-817.]). For a related structure, see: Gowda et al. (2009[Gowda, B. T., Foro, S., Sowmya, B. P., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o389.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data
  • C10H20N4O3

  • Mr = 244.3

  • Triclinic, [P \overline 1]

  • a = 8.1923 (17) Å

  • b = 8.7859 (16) Å

  • c = 9.714 (2) Å

  • [alpha] = 109.451 (7)°

  • [beta] = 99.540 (7)°

  • [gamma] = 96.474 (7)°

  • V = 639.5 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 300 K

  • 0.22 × 0.16 × 0.1 mm

Data collection
  • Bruker SMART X2S diffractometer

  • 6407 measured reflections

  • 2218 independent reflections

  • 1632 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.130

  • S = 1.05

  • 2218 reflections

  • 162 parameters

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2D...O1 0.94 (3) 2.08 (3) 2.538 (2) 108.3 (19)
N2-H2C...O2i 0.89 (3) 2.10 (3) 2.988 (2) 173 (3)
O1-H1...N1ii 0.82 2.04 2.764 (3) 147
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+3, -z+2.

Data collection: SMART (Bruker, 2004[Bruker (2004). SMART, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SMART, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). SMART, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZJ2096 ).


Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, Tumkur for his constant encouragement. and G. B. Sadananda, Department of Studies and Research in Physics, U. C. S. Tumkur University, Tumkur, for his help and valuable suggestions. BSPM thanks Dr H. C. Devarajegowda, Department of Physics Yuvarajas College (constituent), University of Mysore, for his guidance.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). SMART, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gan, L. L., Cai, J. L. & Zhou, C. H. (2009a). Chin. Pharm. J. 44, 1361-1368.  [ChemPort]
Gan, L. L., Lu, Y. H. & Zhou, C. H. (2009b). Chin. J. Biochem. Pharm. 30, 127-131.  [ChemPort]
Gowda, B. T., Foro, S., Sowmya, B. P., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o389.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Willems, L. I. & Ilzerman, A. P. (2010). Med. Chem. Res. 30, 778-817.  [ChemPort]


Acta Cryst (2012). E68, o3347  [ doi:10.1107/S1600536812046223 ]

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