[Journal logo]

Volume 69 
Part 10 
Pages o1531-o1532  
October 2013  

Received 25 July 2013
Accepted 3 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.053
wR = 0.147
Data-to-parameter ratio = 14.9
Details
Open access

tert-Butyl N-{[5-(5-oxohexanamido)pyridin-2-yl]amino}carbamate

aUniversité Bordeaux Segalen, CNRS FRE 3396 -Pharmacochimie, F-33076 Bordeaux, France, and bISM-CNRS UMR 5255, Université de Bordeaux, F-33405 Talence cedex, France
Correspondence e-mail: jean.guillon@u-bordeaux2.fr

In the crystal structure of the title compound, C16H24N4O4, molecules are linked by N-H...O hydrogen bonds between the carbonyl groups of the carbamoyl and amido functional groups and the amino groups, and by N-H...N hydrogen bonds between the amino group and the pyridine ring, forming two-dimensional networks parallel to the ab plane.

Related literature

For the synthesis, properties and biological activity of 2-hydrazinopyridine derivatives, see: Ardisson et al. (2005[Ardisson, V., Mathieu, J. P., Ghezzi, C. & Fagret, D. (2005). Med. Nucl. 29, 168-178.]); Jurisson & Lydon (1999[Jurisson, S. S. & Lydon, J. D. (1999). Chem. Rev. 99, 2205-2218.]); Abrams et al. (1994[Abrams, M. J., Bridger, G. J., Schwartz, D. A., Padmanabhan, S. & Ultee, M. E. (1994). World Patent WO 94/10149.]); Liu et al. (2011[Liu, L., Zhang, M., Zhong, G. & Wang, X. (2011). J. Radioanal. Nucl. Chem. 287, 847-852.]); Lu et al. (2011[Lu, J., Pang, Y., Xie, F., Guo, H.-J., Li, Y., Yang, Z. & Wang, X.-B. (2011). Nucl. Med. Biol. 38, 557-565.]); Schwartz et al. (1990[Schwartz, D. A., Abrams, M. J., Giandomenico, C. M. & Zubieta, J. A. (1990). Eur. Patent EP 384769.]). For the crystal structures of related compounds, see: Banerjee et al. (2005[Banerjee, S. R., Schaffer, P., Babich, J. W., Valliant, J. F. & Zubieta, J. (2005). Dalton Trans. pp. 3886-3897.]); Rose et al. (1998[Rose, D. J., Maresca, K. P., Nicholson, T., Davison, A., Jones, A. G., Babich, J., Fischman, A., Graham, W., DeBord, J. R. D. & Zubieta, J. (1998). Inorg. Chem. 37, 2701-2716.]); Zora et al. (2006[Zora, M., Turgut, G., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o2677-o2679.]). For synthesis, see: Cugola et al. (1995[Cugola, A., Di Fabio, R. & Pentasuglia, G. (1995). World Patent WO 95/10517.]).

[Scheme 1]

Experimental

Crystal data
  • C16H24N4O4

  • Mr = 336.39

  • Triclinic, [P \overline 1]

  • a = 6.2598 (4) Å

  • b = 9.2822 (6) Å

  • c = 16.0437 (12) Å

  • [alpha] = 84.387 (6)°

  • [beta] = 88.957 (6)°

  • [gamma] = 79.358 (6)°

  • V = 911.79 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.84 × 0.17 × 0.06 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.928, Tmax = 0.994

  • 20299 measured reflections

  • 3295 independent reflections

  • 2187 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.147

  • S = 1.04

  • 3295 reflections

  • 221 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.86 2.06 2.888 (2) 161
N3-H3...N2ii 0.86 2.21 2.957 (3) 145
N4-H4...O2iii 0.86 2.06 2.827 (3) 149
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+2; (iii) -x+1, -y+1, -z+2.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg, 1992[Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2115 ).


Acknowledgements

This publication was supported by a grant from the Ligue Nationale contre le Cancer (Comité Aquitaine-Charentes, Bordeaux, France).

References

Abrams, M. J., Bridger, G. J., Schwartz, D. A., Padmanabhan, S. & Ultee, M. E. (1994). World Patent WO 94/10149.
Ardisson, V., Mathieu, J. P., Ghezzi, C. & Fagret, D. (2005). Med. Nucl. 29, 168-178.
Banerjee, S. R., Schaffer, P., Babich, J. W., Valliant, J. F. & Zubieta, J. (2005). Dalton Trans. pp. 3886-3897.  [CSD] [CrossRef]
Cugola, A., Di Fabio, R. & Pentasuglia, G. (1995). World Patent WO 95/10517.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jurisson, S. S. & Lydon, J. D. (1999). Chem. Rev. 99, 2205-2218.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Liu, L., Zhang, M., Zhong, G. & Wang, X. (2011). J. Radioanal. Nucl. Chem. 287, 847-852.  [Web of Science] [CrossRef] [ChemPort]
Lu, J., Pang, Y., Xie, F., Guo, H.-J., Li, Y., Yang, Z. & Wang, X.-B. (2011). Nucl. Med. Biol. 38, 557-565.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Rose, D. J., Maresca, K. P., Nicholson, T., Davison, A., Jones, A. G., Babich, J., Fischman, A., Graham, W., DeBord, J. R. D. & Zubieta, J. (1998). Inorg. Chem. 37, 2701-2716.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Schwartz, D. A., Abrams, M. J., Giandomenico, C. M. & Zubieta, J. A. (1990). Eur. Patent EP 384769.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zora, M., Turgut, G., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o2677-o2679.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1531-o1532   [ doi:10.1107/S1600536813024598 ]

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.