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Volume 69 
Part 12 
Page o1769  
December 2013  

Received 11 October 2013
Accepted 26 October 2013
Online 13 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.104
Data-to-parameter ratio = 12.9
Details
Open access

N'-Benzoyl-5-methyl-1,3-diphenyl-1H-pyrazole-4-carbohydrazide

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India,bDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, and cDepartment of Physics, SJB Institute of Technology, Kengeri, Bangalore 560 060, India
Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

In the title compound, C24H20N4O2, the pyrazole ring makes dihedral angles of 47.57 (10)° and 30.56 (11)° with its N-bound and C-bound phenyl groups, respectively. The C-N-N-C group that links the two carbonyls has a torsion angle of 81.5 (2)°. The torsion angles between the carbonyl groups and their adjacent pyrazole and phenyl rings are 125.89 (19) and 164.22 (17)°, respectively. In the crystal, pairs of mol­ecules are linked by N-H...O hydrogen bonds into R22(10) ring motifs, which in turn link to form chains that propagate parallel to the c-axis direction.

Related literature

For the biological activity of pyrazoles, see: Cunico et al. (2006[Cunico, W., Cechinel, C. A., Bonacorso, H. G., Martins, M. A. P., Zanatta, N., Souza, M. V. N., Freitas, I. O., Soaresa, R. P. & Krettli, A. U. (2006). Bioorg. Med. Chem. 16, 649-653.]); Farag et al. (2008[Farag, A. M., Mayhoub, A. S., Barakatb, S. E. & Bayomi, A. H. (2008). Bioorg. Med. Chem. Lett. 16, 881-889.]); Sharma et al. (2010[Sharma, P. K., Kumar, S., Kumar, P., Kaushik, P., Kaushik, D., Dhingra, Y. & Aneja, K. R. (2010). Eur. J. Med. Chem. 45, 2650-2655.]); Patel et al. (2004[Patel, M. V., Bell, R., Majest, S., Henry, R. & Kolasa, T. (2004). J. Org. Chem. 69, 7058-7065.]). For the synthesis of pyrazoles, see: Shridevi Doddaramappa et al. (2013[Shridevi Doddaramappa, D., Chandra, Mahendra, M. & Lokanatha Rai, K. M. (2013). Chem. Heterocycl. Compd, 49, 698-703.]). For bond-length and angle data in a related structure, see: Chandra et al. (2012[Chandra, , Srikantamurthy, N., Umesha, K. B., Jeyaseelan, S. & Mahendra, M. (2012). Acta Cryst. E68, o1661-o1662.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20N4O2

  • Mr = 396.44

  • Monoclinic, P 21 /c

  • a = 22.399 (15) Å

  • b = 11.180 (8) Å

  • c = 8.190 (6) Å

  • [beta] = 97.378 (12)°

  • V = 2034 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 18837 measured reflections

  • 3601 independent reflections

  • 2793 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.104

  • S = 1.04

  • 3601 reflections

  • 280 parameters

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N21-H21...O20i 0.88 (2) 2.05 (2) 2.925 (3) 174.5 (17)
N22-H22...O24ii 0.90 (2) 1.98 (2) 2.864 (3) 167.7 (17)
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: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2500 ).


Acknowledgements

The authors would like to thank the UGC, New Delhi, Government of India, for awarding a project under the head F. No. 41-920/2012(SR) dated: 25-07-2012.

References

Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chandra, , Srikantamurthy, N., Umesha, K. B., Jeyaseelan, S. & Mahendra, M. (2012). Acta Cryst. E68, o1661-o1662.
Cunico, W., Cechinel, C. A., Bonacorso, H. G., Martins, M. A. P., Zanatta, N., Souza, M. V. N., Freitas, I. O., Soaresa, R. P. & Krettli, A. U. (2006). Bioorg. Med. Chem. 16, 649-653.  [ChemPort]
Farag, A. M., Mayhoub, A. S., Barakatb, S. E. & Bayomi, A. H. (2008). Bioorg. Med. Chem. Lett. 16, 881-889.  [ChemPort]
Patel, M. V., Bell, R., Majest, S., Henry, R. & Kolasa, T. (2004). J. Org. Chem. 69, 7058-7065.  [CSD] [CrossRef] [PubMed] [ChemPort]
Sharma, P. K., Kumar, S., Kumar, P., Kaushik, P., Kaushik, D., Dhingra, Y. & Aneja, K. R. (2010). Eur. J. Med. Chem. 45, 2650-2655.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shridevi Doddaramappa, D., Chandra, Mahendra, M. & Lokanatha Rai, K. M. (2013). Chem. Heterocycl. Compd, 49, 698-703.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1769  [ doi:10.1107/S1600536813029528 ]

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