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Volume 68 
Part 12 
Page o3436  
December 2012  

Received 12 November 2012
Accepted 18 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.096
Data-to-parameter ratio = 14.5
Details
Open access

2-(2-Nitrophenyl)acetohydrazide

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C8H9N3O3, the dihedral angle between the benzene ring and the acetohydrazide C-C(=O)-N-N plane [maximum deviation = 0.0471 (13) Å] is 87.62 (8)°. The nitro group is twisted by 19.3 (2)° with respect to the benzene ring. In the crystal, N-H...O hydrogen bonds link the molecules into a double-column structure along the b axis.

Related literature

For the chemistry of hydrazides, ses: Domiano et al. (1984[Domiano, P., Pelizzi, C. & Predieri, G. (1984). Polyhedron, 3, 281-286.]). For the biological properties of hydrazides, see: Kalsi et al. (2006[Kalsi, R., Shrimali, M., Bhalla, T. N. & Barthwal, J. P. (2006). Indian J. Pharm. Sci. 41, 353-359.]); Masunari & Tavares (2007[Masunari, A. & Tavares, L. C. (2007). Bioorg. Med. Chem. 15, 4229-4236.]); Singh et al. (1992[Singh, V., Srivastava, V. K., Palit, G. & Shanker, K. (1992). Arzneim. Forsch. Drug Res. 42, 993-996.]). For related structures, see: Ahmad et al. (2012[Ahmad, S., Jabbar, A., Hussain, M. T. & Tahir, M. N. (2012). Acta Cryst. E68, o2269.]); Dutkiewicz et al. (2009[Dutkiewicz, G., Chidan Kumar, C. S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2009). Acta Cryst. E65, o3189.]); Liu & Gao (2012[Liu, G. & Gao, J. (2012). Acta Cryst. E68, o1969.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C8H9N3O3

  • Mr = 195.18

  • Monoclinic, P 21

  • a = 6.6962 (5) Å

  • b = 4.9388 (4) Å

  • c = 13.3593 (12) Å

  • [beta] = 92.361 (8)°

  • V = 441.43 (6) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.98 mm-1

  • T = 173 K

  • 0.36 × 0.28 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.667, Tmax = 0.925

  • 3829 measured reflections

  • 1967 independent reflections

  • 1824 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.096

  • S = 1.05

  • 1967 reflections

  • 136 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 836 Friedel pairs

  • Flack parameter: 0.3 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1B...O1i 0.90 (1) 2.21 (2) 3.0752 (19) 163 (2)
N2-H2...O1ii 0.85 (2) 2.03 (2) 2.8531 (18) 165 (2)
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+1]; (ii) x, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED; 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5219 ).


Acknowledgements

ASP thanks UOM for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Ahmad, S., Jabbar, A., Hussain, M. T. & Tahir, M. N. (2012). Acta Cryst. E68, o2269.  [CSD] [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Domiano, P., Pelizzi, C. & Predieri, G. (1984). Polyhedron, 3, 281-286.  [CrossRef] [ChemPort] [ISI]
Dutkiewicz, G., Chidan Kumar, C. S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2009). Acta Cryst. E65, o3189.  [CSD] [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Kalsi, R., Shrimali, M., Bhalla, T. N. & Barthwal, J. P. (2006). Indian J. Pharm. Sci. 41, 353-359.
Liu, G. & Gao, J. (2012). Acta Cryst. E68, o1969.  [CSD] [CrossRef] [details]
Masunari, A. & Tavares, L. C. (2007). Bioorg. Med. Chem. 15, 4229-4236.  [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, V., Srivastava, V. K., Palit, G. & Shanker, K. (1992). Arzneim. Forsch. Drug Res. 42, 993-996.  [ChemPort]


Acta Cryst (2012). E68, o3436  [ doi:10.1107/S1600536812047381 ]

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