2-(2-Nitro­phen­yl)acetohydrazide

Praveen, A.S.; Jasinski, J.P.; Keeley, A.C.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536812047381

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 (C-C) = 0.002 Å
R = 0.038
wR = 0.096
Data-to-parameter ratio = 14.5
Details

2-(2-Nitrophenyl)acetohydrazide

A. S. Praveen,^a Jerry P. Jasinski,^b ^* Amanda C. Keeley,^b H. S. Yathirajan ^a and B. Narayana ^c

^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-HO 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). For the biological properties of hydrazides, see: Kalsi et al. (2006); Masunari & Tavares (2007); Singh et al. (1992). For related structures, see: Ahmad et al. (2012); Dutkiewicz et al. (2009); Liu & Gao (2012). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₈H₉N₃O₃
M_r = 195.18
Monoclinic, P 2₁
a = 6.6962 (5) Å
b = 4.9388 (4) Å
c = 13.3593 (12) Å
= 92.361 (8)°
V = 441.43 (6) Å³
Z = 2
Cu K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.667, T_max = 0.925
3829 measured reflections
1967 independent reflections
1824 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(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
_max = 0.19 e Å^-3
_min = -0.17 e Å^-3
Absolute structure: Flack (1983), 836 Friedel pairs
Flack parameter: 0.3 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1BO1ⁱ	0.90 (1)	2.21 (2)	3.0752 (19)	163 (2)
N2-H2O1ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
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.
Dutkiewicz, G., Chidan Kumar, C. S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2009). Acta Cryst. E65, o3189.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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.
Masunari, A. & Tavares, L. C. (2007). Bioorg. Med. Chem. 15, 4229-4236.
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, V., Srivastava, V. K., Palit, G. & Shanker, K. (1992). Arzneim. Forsch. Drug Res. 42, 993-996.

organic compounds