2-(4-Methyl­phen­yl)acetohydrazide

Praveen, A.S.; Jasinski, J.P.; Krauss, S.T.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S160053681204799X

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 (C-C) = 0.003 Å
R = 0.050
wR = 0.151
Data-to-parameter ratio = 14.1
Details

2-(4-Methylphenyl)acetohydrazide

A.S. Praveen,^a Jerry P. Jasinski,^b ^* Shannon T. Krauss,^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, C₉H₁₂N₂O, the dihedral angle between the benzene ring and the mean plane of the acetohydrazide group is 88.2 (7)°. In the crystal, N-HO hydrogen bonds and weak C-HO 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). For related structures, see: Hanif et al. (2007); Liu & Gao (2012); Fun et al. (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₉H₁₂N₂O
M_r = 164.21
Monoclinic, P 2₁ /c
a = 15.4261 (16) Å
b = 6.2618 (7) Å
c = 9.2073 (10) Å
= 106.651 (12)°
V = 852.09 (16) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.746, T_max = 1.000
4845 measured reflections
1675 independent reflections
1359 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(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
_max = 0.26 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.84 (2)	2.05 (2)	2.884 (2)	171 (2)
C2-H2AO1ⁱ	0.97	2.56	3.408 (2)	146
N1-H1AO1ⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); 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: 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.
Hanif, M., Qadeer, G., Rama, N. H., Farman, M. & Ruzicka, A. (2007). Acta Cryst. E63, o4828.
Liu, G. & Gao, J. (2012). Acta Cryst. E68, o1969.
Narayana, B., Ashalatha, B. V., Vijayaraj, K. K., Fernandes, J. & Sarojini, B. K. (2005). Bioorg. Med. Chem. 13, 4638-4644.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds