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Volume 69 
Part 4 
Page o602  
April 2013  

Received 6 March 2013
Accepted 19 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 301 K
Mean [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.131
Data-to-parameter ratio = 18.0
Details
Open access

3-Methyl-1,5-diphenyl-4,5-dihydro-1H-pyrazole

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bPost Graduate Department of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title compound, C16H16N2, the dihydropyrazole ring adopts a shallow envelope conformation, with the C atom bearing the phenyl group displaced by 0.298 (2) Å from the other atoms (r.m.s. deviation = 0.015 Å). The dihedral angles between the four near coplanar atoms of the central ring and the N- and C-bonded phenyl groups are 13.49 (13) and 82.22 (16)°, respectively.

Related literature

For background to pyrazoles, see: Govindaraju et al. (2012[Govindaraju, M., Vasanth Kumar, G., Pavithra, G., Harish Nayaka, M. A., Mylarappa, B. N. & Ajay Kumar, K. (2012). IOSR J. Pharm. Biol. Sci. 2, 30-34.]); Jayaroopa et al. (2013[Jayaroopa, P., Vasanth Kumar, G., Renuka, N., Harish Nayaka, M. A. & Ajay Kumar, K. (2013). Int. J. PharmTech Res. 5, 264-270.]); Kalirajan et al. (2013[Kalirajan, R., Leela, R., Jubie, S., Gowramma, B., Gomathi, S. & Sankar, S. (2013). Indian J. Chem. Sect. B, 50, 1794-1799.]); Mariappan et al. (2010[Mariappan, G., Saha, B. P., Sutharson, L. & Haldar, A. (2010). Indian J. Chem. Sect. B, 49, 1671-1674.]); Shyama et al. (2009[Shyama, S., Robert, A., Ying, S., Sonoko, N., Brown, B., Jose, L. M., Eduard, S. & Nicholas, D. P. C. (2009). Bioorg. Med. Chem. Lett. 19, 222-225.]). For related structures, see: Baktir et al. (2011[Baktir, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o328-o329.]); Fun et al. (2011[Fun, H.-K., Quah, C. K., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2011). Acta Cryst. E67, o3513.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2

  • Mr = 236.31

  • Monoclinic, C c

  • a = 18.1224 (17) Å

  • b = 7.8055 (6) Å

  • c = 12.5057 (13) Å

  • [beta] = 132.207 (9)°

  • V = 1310.3 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 301 K

  • 0.32 × 0.20 × 0.18 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 11856 measured reflections

  • 2973 independent reflections

  • 2362 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.131

  • S = 0.91

  • 2973 reflections

  • 165 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.10 e Å-3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7053 ).


Acknowledgements

MM thanks the IOE, University of Mysore, for the award of a fellowship. We thank the Solid Sate and Structural Chemistry Unit, IISc, Bangalore, for the data collection.

References

Baktir, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o328-o329.  [CSD] [CrossRef] [details]
Fun, H.-K., Quah, C. K., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2011). Acta Cryst. E67, o3513.  [CrossRef] [details]
Govindaraju, M., Vasanth Kumar, G., Pavithra, G., Harish Nayaka, M. A., Mylarappa, B. N. & Ajay Kumar, K. (2012). IOSR J. Pharm. Biol. Sci. 2, 30-34.
Jayaroopa, P., Vasanth Kumar, G., Renuka, N., Harish Nayaka, M. A. & Ajay Kumar, K. (2013). Int. J. PharmTech Res. 5, 264-270.
Kalirajan, R., Leela, R., Jubie, S., Gowramma, B., Gomathi, S. & Sankar, S. (2013). Indian J. Chem. Sect. B, 50, 1794-1799.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Mariappan, G., Saha, B. P., Sutharson, L. & Haldar, A. (2010). Indian J. Chem. Sect. B, 49, 1671-1674.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shyama, S., Robert, A., Ying, S., Sonoko, N., Brown, B., Jose, L. M., Eduard, S. & Nicholas, D. P. C. (2009). Bioorg. Med. Chem. Lett. 19, 222-225.  [PubMed]


Acta Cryst (2013). E69, o602  [ doi:10.1107/S1600536813007575 ]

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