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Volume 68 
Part 7 
Page o2162  
July 2012  

Received 11 June 2012
Accepted 15 June 2012
Online 23 June 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.074
wR = 0.187
Data-to-parameter ratio = 19.0
Details
Open access

3-Methyl-4-[2-(4-nitrophenyl)hydrazin-1-ylidene]-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothioamide

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

The asymmetric unit of the title compound, C11H10N6O3S, contains two independent molecules, each of which is stabilized by an intramolecular N-H...O hydrogen bond, forming an S(6) ring motif. In one molecule, the pyrazole ring forms a dihedral angle of 10.93 (14)° with the benzene ring. The corresponding dihedral angle in the other molecule is 7.03 (14)°. In the crystal, molecules are linked via pairs of (N,N)-H...O bifurcated acceptor bonds which, together with C-H...O hydrogen bonds, form sheets parallel to (001).

Related literature

For general background to and the pharmacological activity of pyrazole derivatives, see: Isloor et al. (2009[Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.]); Rai et al. (2008[Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715-1720.]); Bradbury & Pucci (2008[Bradbury, B. J. & Pucci, M. J. (2008). Curr. Opin. Pharmacol. 8, 574-581.]); Girisha et al. (2010[Girisha, K. S., Kalluraya, B., Narayana, V. & Padmashree (2010). Eur. J. Med. Chem. 45, 4640-4644.]). 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 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.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10N6O3S

  • Mr = 306.31

  • Monoclinic, P 21 /c

  • a = 11.5331 (4) Å

  • b = 17.2540 (6) Å

  • c = 13.6025 (5) Å

  • [beta] = 105.840 (2)°

  • V = 2604.01 (16) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 100 K

  • 0.23 × 0.19 × 0.13 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.940, Tmax = 0.965

  • 29927 measured reflections

  • 7706 independent reflections

  • 5153 reflections with I > 2[sigma](I)

  • Rint = 0.086

Refinement
  • R[F2 > 2[sigma](F2)] = 0.074

  • wR(F2) = 0.187

  • S = 1.05

  • 7706 reflections

  • 405 parameters

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

  • [Delta][rho]max = 1.17 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N5B-H2N5...O3B 0.97 (3) 2.08 (3) 2.810 (3) 131 (3)
N1A-H1N1...O3Bi 0.88 (4) 2.00 (4) 2.859 (3) 165 (4)
N5A-H1N5...O3A 0.92 (3) 2.11 (4) 2.802 (3) 131 (3)
N1B-H3N1...O3Aii 0.87 (3) 1.99 (4) 2.848 (3) 171 (3)
C10B-H10B...O2Aiii 0.95 2.51 3.418 (3) 161
Symmetry codes: (i) x, y-1, z; (ii) x-1, y+1, z; (iii) x-1, y, z.

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: KJ2205 ).


Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for an Incentive Grant.

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. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bradbury, B. J. & Pucci, M. J. (2008). Curr. Opin. Pharmacol. 8, 574-581.  [ISI] [PubMed] [ChemPort]
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]
Girisha, K. S., Kalluraya, B., Narayana, V. & Padmashree (2010). Eur. J. Med. Chem. 45, 4640-4644.
Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.  [ISI] [CrossRef] [PubMed] [ChemPort]
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]


Acta Cryst (2012). E68, o2162  [ doi:10.1107/S1600536812027134 ]

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