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Volume 68 
Part 12 
Page o3467  
December 2012  

Received 16 November 2012
Accepted 21 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.151
Data-to-parameter ratio = 14.1
Details
Open access

2-(4-Methylphenyl)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, C9H12N2O, the dihedral angle between the benzene ring and the mean plane of the acetohydrazide group is 88.2 (7)°. In the crystal, N-H...O hydrogen bonds and weak C-H...O interactions link the molecules into infinite ribbons along [001].

Related literature

For hydrazides as precursors in the synthesis of heterocyclic systems, see: Narayana et al. (2005[Narayana, B., Ashalatha, B. V., Vijayaraj, K. K., Fernandes, J. & Sarojini, B. K. (2005). Bioorg. Med. Chem. 13, 4638-4644.]). For related structures, see: Hanif et al. (2007[Hanif, M., Qadeer, G., Rama, N. H., Farman, M. & Ruzicka, A. (2007). Acta Cryst. E63, o4828.]); Liu & Gao (2012[Liu, G. & Gao, J. (2012). Acta Cryst. E68, o1969.]); Fun et al. (2011[Fun, H.-K., Quah, C. K., Malladi, S. M. V. A. & Isloor, A. M. (2011). Acta Cryst. E67, o165.]). For standard bond lengths, 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
  • C9H12N2O

  • Mr = 164.21

  • Monoclinic, P 21 /c

  • a = 15.4261 (16) Å

  • b = 6.2618 (7) Å

  • c = 9.2073 (10) Å

  • [beta] = 106.651 (12)°

  • V = 852.09 (16) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.69 mm-1

  • T = 173 K

  • 0.32 × 0.22 × 0.08 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.746, Tmax = 1.000

  • 4845 measured reflections

  • 1675 independent reflections

  • 1359 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.151

  • S = 1.07

  • 1675 reflections

  • 119 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1i 0.84 (2) 2.05 (2) 2.884 (2) 171 (2)
C2-H2A...O1i 0.97 2.56 3.408 (2) 146
N1-H1A...O1ii 0.89 (2) 2.16 (2) 3.007 (2) 159 (2)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); 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: NG5307 ).


Acknowledgements

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

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
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.
Fun, H.-K., Quah, C. K., Malladi, S. M. V. A. & Isloor, A. M. (2011). Acta Cryst. E67, o165.  [CrossRef] [details]
Hanif, M., Qadeer, G., Rama, N. H., Farman, M. & Ruzicka, A. (2007). Acta Cryst. E63, o4828.  [CSD] [CrossRef] [details]
Liu, G. & Gao, J. (2012). Acta Cryst. E68, o1969.  [CSD] [CrossRef] [details]
Narayana, B., Ashalatha, B. V., Vijayaraj, K. K., Fernandes, J. & Sarojini, B. K. (2005). Bioorg. Med. Chem. 13, 4638-4644.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3467  [ doi:10.1107/S160053681204799X ]

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