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

Sreenivasa, S.; Manojkumar, K.E.; Suchetan, P.A.; Mohan, N.R.; Palakshamurthy, B.S.

doi:10.1107/S1600536812046223

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 (C-C) = 0.003 Å
R = 0.044
wR = 0.130
Data-to-parameter ratio = 13.7
Details

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

S. Sreenivasa,^a ^* K. E. Manojkumar,^a P. A. Suchetan,^b N. R. Mohan ^a and B. S. Palakshamurthy ^c

^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-HO contact occurs involving the NH₂ group and the oxime O atom. In the crystal, molecules are linked via strong N-HO and O-HN 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,b); Willems & Ilzerman (2010). For a related structure, see: Gowda et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter (1990).

Experimental

Crystal data

C₁₀H₂₀N₄O₃
M_r = 244.3
Triclinic, $[P \overline 1]$
a = 8.1923 (17) Å
b = 8.7859 (16) Å
c = 9.714 (2) Å
= 109.451 (7)°
= 99.540 (7)°
= 96.474 (7)°
V = 639.5 (2) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.027

Refinement

R[F² > 2(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
_max = 0.21 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2DO1	0.94 (3)	2.08 (3)	2.538 (2)	108.3 (19)
N2-H2CO2ⁱ	0.89 (3)	2.10 (3)	2.988 (2)	173 (3)
O1-H1N1ⁱⁱ	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); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); 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.
Bruker (2004). SMART, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gan, L. L., Cai, J. L. & Zhou, C. H. (2009a). Chin. Pharm. J. 44, 1361-1368.
Gan, L. L., Lu, Y. H. & Zhou, C. H. (2009b). Chin. J. Biochem. Pharm. 30, 127-131.
Gowda, B. T., Foro, S., Sowmya, B. P., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o389.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Willems, L. I. & Ilzerman, A. P. (2010). Med. Chem. Res. 30, 778-817.

organic compounds