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Volume 69 
Part 12 
Page o1736  
December 2013  

Received 7 October 2013
Accepted 20 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.133
Data-to-parameter ratio = 13.4
Details
Open access

5-Methyl-1,3-diphenyl-N-(5-phenyl-1,3,4-thia­diazol-2-yl)-1H-pyrazole-4-carboxamide

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India,bDepartment of Physics, Acharya Institute of Technology, Bangalore 560 090, India,cDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, and dSER-CAT, APS, Argonne National Laboratory, Argonne, IL-60439, USA
Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

The asymmetric unit of the title compound C25H19N5OS, contains two mol­ecules, A and B. In mol­ecule A, the dihedral angles between the pyrazole ring and the C-bound phenyl group, the N-bound phenyl group and the thia­diazole ring are 32.30 (14), 52.25 (14) and 34.94 (12)°, respectively. The corresponding angles in mol­ecule B are 33.32 (14), 50.67 (15), and 70.30 (12)°, respectively. In the crystal, the A and B mol­ecules are linked by pairs of N-H...N hydrogen bonds, generating R22(8) loops. This dimer linkage is reinforced by two C-H...O hydrogen bonds and one C-H...N hydrogen bond.

Related literature

For the synthesis, see: Shridevi Doddaramappa et al. (2013[Shridevi Doddaramappa, D., Chandra., Mahendra, M. & Lokanatha Rai, K. M. (2013). Chem. Heterocycl. Compd, 49, 698-703.]). For 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
  • C25H19N5OS

  • Mr = 437.52

  • Triclinic, [P \overline 1]

  • a = 10.7039 (14) Å

  • b = 12.9341 (17) Å

  • c = 17.478 (2) Å

  • [alpha] = 77.343 (2)°

  • [beta] = 82.865 (2)°

  • [gamma] = 70.373 (2)°

  • V = 2220.4 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 273 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 18748 measured reflections

  • 7768 independent reflections

  • 5447 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.133

  • S = 1.02

  • 7768 reflections

  • 579 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H21...N9B 0.86 2.13 2.916 (3) 151
N8B-H53...N4A 0.86 2.07 2.902 (3) 163
C4A-H6B...O1A 0.96 2.42 3.107 (3) 128
C29B-H38C...N5A 0.96 2.59 3.443 (3) 148
C37B-H46...O2B 0.93 2.41 3.184 (3) 141

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: HB7148 ).


Acknowledgements

Chandra would like to thank the University of Mysore for the award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009-2010/10.07.2012.

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.
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, o1736  [ doi:10.1107/S1600536813028766 ]

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