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Volume 67 
Part 10 
Page o2670  
October 2011  

Received 12 September 2011
Accepted 12 September 2011
Online 17 September 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.063
wR = 0.135
Data-to-parameter ratio = 19.8
Details
Open access

4-[2-(4-Chlorophenyl)hydrazinylidene]-3-methyl-1H-pyrazol-5(4H)-one

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C10H9ClN4O, the pyrazole ring [maximum deviation = 0.014 (2) Å] forms a dihedral angle of 7.06 (14)° with the chlorobenzene ring. The molecular conformation is stabilized by an intramolecular N-H...O hydrogen bond, which generates an S(6) ring motif. In the crystal, inversion dimers linked by pairs of C-H...O hydrogen bonds generate R22(16) ring motifs. The dimers are further connected by N-H...N hydrogen bonds, thereby forming layers lying parallel to the bc plane.

Related literature

For general background to and applications of pyrazole derivatives, see: Rai & Kalluraya (2006[Rai, N. S. & Kalluraya, B. (2006). Indian J. Chem. Sect. B, 46, 375-378.]); Rai et al. (2008[Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715-1720.]); Sridhar & Perumal (2003[Sridhar, R. & Perumal, P. T. (2003). Synth. Commun. 33, 1483-1488.]). For standard 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.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9ClN4O

  • Mr = 236.66

  • Monoclinic, P 21 /c

  • a = 15.8496 (5) Å

  • b = 3.8184 (1) Å

  • c = 20.3794 (6) Å

  • [beta] = 123.575 (2)°

  • V = 1027.59 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 100 K

  • 0.55 × 0.06 × 0.05 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.829, Tmax = 0.984

  • 11013 measured reflections

  • 3048 independent reflections

  • 2213 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.135

  • S = 1.08

  • 3048 reflections

  • 154 parameters

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

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.49 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O1 0.93 (3) 2.15 (3) 2.841 (3) 131 (3)
N3-H1N3...N4i 0.87 (3) 2.16 (3) 2.983 (3) 158 (3)
C5-H5A...O1ii 0.95 2.47 3.334 (3) 151
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6405 ).


Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

References

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Rai, N. S. & Kalluraya, B. (2006). Indian J. Chem. Sect. B, 46, 375-378.
Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715-1720.  [ISI] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sridhar, R. & Perumal, P. T. (2003). Synth. Commun. 33, 1483-1488.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2011). E67, o2670  [ doi:10.1107/S1600536811037020 ]

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