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Volume 69 
Part 8 
Page o1305  
August 2013  

Received 7 July 2013
Accepted 17 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.058
wR = 0.142
Data-to-parameter ratio = 12.2
Details
Open access

2-Hydroxy-N'-methyl-5-nitrobenzohydrazide

aCollege of Chemistry and Material Science, South-Central University for Nationalities, Wuhan 430074, People's Republic of China
Correspondence e-mail: longfei.jin@yahoo.com

In the title compound, C8H9N3O4, there are two molecules in the asymmetric unit, one of which is in the zwitterionic form. The zwitterion contains an intramolecular N-H...O hydrogen bond and the other molecule contains both an intramolecular N-H...O and an intramolecular O-H...O hydrogen bond. In the crystal, N-H...O and N-H...N hydrogen bonds link the molecules, formimg a two-dimensional network parallel to (10-1).

Related literature

For the biological activities of salicylhydrazide derivatives, see: Bagchi et al. (2004[Bagchi, M. C., Maiti, B. C. & Bose, S. (2004). J. Mol. Struct. (Theochem), 679, 179-186.]); Thompson et al. (2004[Thompson, S. A., Wheat, L., Brown, N. A., Wingrove, P. B., Pillai, G. V., Whiting, P. G., Adkins, C., Woodward, C. H., Smith, A. J., Simpson, P. B., Collins, I. & Wafford, K. A. (2004). Br. J. Pharmacol. 142, 97-106.]); Al-Mawsawi et al. (2007[Al-Mawsawi, L. Q., Dayam, R., Taheri, L., Witvrouw, M., Debyser, Z. & Neamati, N. (2007). Bioorg. Med. Chem. Lett. 17, 6472-6475.]). For metal complexes involving derivatives of the title compound, see: Jin et al. (2006a[Jin, L.-F., Xiao, F.-P., Cheng, G.-Z. & Ji, Z.-P. (2006a). Inorg. Chem. Commun. 9, 758-760.],b[Jin, L.-F., Xiao, F.-P., Cheng, G.-Z. & Ji, Z.-P. (2006b). J. Organomet. Chem. 691, 2909-2914.]). For related crystal structures, see: Liu et al. (2006[Liu, M.-L., Dou, J.-M., Li, D.-C. & Wang, D.-Q. (2006). Acta Cryst. E62, o1009-o1010.]); Luo et al. (2007[Luo, W., Meng, X.-G., Li, X., Cheng, G.-Z. & Ji, Z.-P. (2007). Acta Cryst. E63, m2482.]); Xu & Liu (2006[Xu, H.-M. & Liu, S.-X. (2006). Acta Cryst. E62, o3026-o3027.]); Zhang (2012[Zhang, X. (2012). Acta Cryst. E68, o2686.]).

[Scheme 1]

Experimental

Crystal data
  • C8H9N3O4

  • Mr = 211.18

  • Monoclinic, P 21 /n

  • a = 7.3818 (15) Å

  • b = 13.106 (3) Å

  • c = 18.719 (4) Å

  • [beta] = 95.25 (3)°

  • V = 1803.4 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.26 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.968, Tmax = 0.987

  • 11293 measured reflections

  • 3536 independent reflections

  • 2356 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.142

  • S = 1.06

  • 3536 reflections

  • 291 parameters

  • 5 restraints

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4A...O2 0.90 (2) 1.92 (2) 2.756 (3) 154 (3)
N1-H1...O1 0.90 (2) 1.78 (2) 2.550 (3) 141 (3)
N2-H2B...N5 1.02 (3) 1.84 (3) 2.858 (3) 174 (3)
O5-H5...O6 0.85 (2) 1.74 (2) 2.549 (3) 158 (4)
N5-H5A...O6 0.83 (2) 2.44 (3) 2.719 (3) 101 (2)
N5-H5A...O4i 0.83 (2) 2.46 (2) 3.162 (3) 143 (3)
N2-H2A...O1ii 0.94 (2) 2.08 (3) 2.762 (3) 128 (2)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5633 ).


Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Hubei Province, China (grant No. 2008CDA067), and the Graduate Student Research Funds of South-Central University for Nationalities.

References

Al-Mawsawi, L. Q., Dayam, R., Taheri, L., Witvrouw, M., Debyser, Z. & Neamati, N. (2007). Bioorg. Med. Chem. Lett. 17, 6472-6475.  [PubMed] [ChemPort]
Bagchi, M. C., Maiti, B. C. & Bose, S. (2004). J. Mol. Struct. (Theochem), 679, 179-186.  [CrossRef] [ChemPort]
Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Jin, L.-F., Xiao, F.-P., Cheng, G.-Z. & Ji, Z.-P. (2006a). Inorg. Chem. Commun. 9, 758-760.  [CrossRef] [ChemPort]
Jin, L.-F., Xiao, F.-P., Cheng, G.-Z. & Ji, Z.-P. (2006b). J. Organomet. Chem. 691, 2909-2914.  [CrossRef] [ChemPort]
Liu, M.-L., Dou, J.-M., Li, D.-C. & Wang, D.-Q. (2006). Acta Cryst. E62, o1009-o1010.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Luo, W., Meng, X.-G., Li, X., Cheng, G.-Z. & Ji, Z.-P. (2007). Acta Cryst. E63, m2482.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Thompson, S. A., Wheat, L., Brown, N. A., Wingrove, P. B., Pillai, G. V., Whiting, P. G., Adkins, C., Woodward, C. H., Smith, A. J., Simpson, P. B., Collins, I. & Wafford, K. A. (2004). Br. J. Pharmacol. 142, 97-106.  [CrossRef] [PubMed] [ChemPort]
Xu, H.-M. & Liu, S.-X. (2006). Acta Cryst. E62, o3026-o3027.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Zhang, X. (2012). Acta Cryst. E68, o2686.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1305  [ doi:10.1107/S1600536813019776 ]

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