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Volume 69 
Part 4 
Page o532  
April 2013  

Received 4 March 2013
Accepted 8 March 2013
Online 13 March 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.124
Data-to-parameter ratio = 14.8
Details
Open access

(Z)-4-[2-(2,4-Dimethylphenyl)hydrazinylidene]-3-methylpyrazol-5(1H)-one

aDepartment of Chemistry, P. A. College of Engineering, Mangalore 574 153, India,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India,cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and eDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: jjasinski@keene.edu

The molecule of the title compound, C12H14N4O, is roughly planar, with a dihedral angle of 8.0 (8)° between the benzene and pyrazole rings, and an intramolecular N-H...O hydrogen bond forms an S(6) ring motif. In the crystal, molecules are linked into an inversion dimer by a pair of N-H...O hydrogen bonds, which form an R22(8) ring motif.

Related literature

For the biological activity of pyrazolones, see: Amir & Kumar (2005[Amir, M. & Kumar, S. (2005). Indian. J. Chem. Sect. B, 44, 2532-2537.]); Rao et al. (2008[Rao, B. S., Akberali, P. M., Holla, B. S. & Sarojini, B. K. (2008). J. Pharmacol. Toxicol. 3, 102-103.]); Samshuddin et al. (2011[Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Darshan Raj, C. G. & Raghavendra, R. (2011). Med. Chem. Res. 21, 2012-2022.]). For the radical scavenging capacity of pyrazol-5-ols, see: Sarojini et al. (2010[Sarojini, B. K., Vidyagayatri, M., Darshan Raj, C. G., Barath, B. R. & Manjunatha, H. (2010). Lett. Drug Des. Discov. 7, 214-224.]). For related structures, see: Butcher et al. (2011[Butcher, R. J., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1019.]); Samshuddin et al. (2011[Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Darshan Raj, C. G. & Raghavendra, R. (2011). Med. Chem. Res. 21, 2012-2022.]). For reference 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
  • C12H14N4O

  • Mr = 230.27

  • Monoclinic, P 21 /c

  • a = 5.2926 (2) Å

  • b = 22.1675 (6) Å

  • c = 10.0529 (3) Å

  • [beta] = 101.770 (3)°

  • V = 1154.64 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.72 mm-1

  • T = 123 K

  • 0.51 × 0.24 × 0.08 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.538, Tmax = 0.944

  • 4152 measured reflections

  • 2328 independent reflections

  • 2061 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.124

  • S = 1.05

  • 2328 reflections

  • 157 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O1i 0.88 1.95 2.8233 (15) 172
N4-H4D...O1 0.88 2.00 2.7286 (15) 139
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO ; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, 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: IS5254 ).


Acknowledgements

BKS gratefully acknowledges the Department of Atomic Energy (DAE)/BRNS, Government of India, for providing financial assistance in the BRNS Project (No. 2011/34/20-BRNS/0846). RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, 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.
Amir, M. & Kumar, S. (2005). Indian. J. Chem. Sect. B, 44, 2532-2537.
Butcher, R. J., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1019.  [CSD] [CrossRef] [details]
Rao, B. S., Akberali, P. M., Holla, B. S. & Sarojini, B. K. (2008). J. Pharmacol. Toxicol. 3, 102-103.  [ChemPort]
Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Darshan Raj, C. G. & Raghavendra, R. (2011). Med. Chem. Res. 21, 2012-2022.  [ISI] [CSD] [CrossRef]
Sarojini, B. K., Vidyagayatri, M., Darshan Raj, C. G., Barath, B. R. & Manjunatha, H. (2010). Lett. Drug Des. Discov. 7, 214-224.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o532  [ doi:10.1107/S1600536813006661 ]

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