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Volume 69 
Part 5 
Page o749  
May 2013  

Received 3 April 2013
Accepted 10 April 2013
Online 17 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.103
Data-to-parameter ratio = 19.0
Details
Open access

7-Chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine

aLaboratoire de Chimie Organique Hétérocyclique URAC21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco,bInstitut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 6005, BP 6759, 45067 Orléans Cedex 2, France,cInstitute of Nanmaterials and Nanotechnology, MASCIR, Rabat, Morocco, and dLaboratoire de Chimie du Solide Appliquée, Université Mohammed V-Agdal, Faculté des Sciences, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: i_bassoude@yahoo.fr

The fused pyrazole and pyrimidine rings in the title compound, C13H10ClN3, are almost coplanar, their planes being inclined to one another by 0.8 (2)°. The mean plane of the fused ring system is nearly coplanar with the phenyl ring, as indicated by the dihedral angle between their planes of 9.06 (7)°.

Related literature

For pharmacological and biochemical properties of pyrazolo[1,5-a]pyrimidine derivatives, see: Selleri et al. (2005[Selleri, S., Gratteri, P., Costagli, C., Bonaccini, C., Costanzo, A., Melani, F., Guerrini, G., Ciciani, G., Costa, B., Spinetti, F., Martini, C. & Bruni, F. (2005). Bioorg. Med. Chem. 13, 4821-4834.]); Almansa et al. (2001[Almansa, C. A., Alberto, F., Cavalcanti, F. L., Gomez, L. A., Miralles, A., Merlos, M., Garcia-Rafanell, J. & Forn, J. (2001). J. Med. Chem. 44, 350-361.]); Suzuki et al. (2001[Suzuki, M., Iwasaki, H., Fujikawa, Y., Sakashita, M., Kitahara, M. & Sakoda, R. (2001). Bioorg. Med. Chem. Lett. 11, 1285-1288.]), Chen et al. (2004[Chen, C., Wilcoxen, K. M., Huang, C. Q., Xie, Y.-F., McCarthy, J. R., Webb, T. R., Zhu, Y.-F., Saunders, J., Liu, X.-J., Chen, T.-K., Bozigian, H. & Grigoriadis, D. E. (2004). J. Med. Chem. 47, 4787-4798.]). For related structures, see: Senga et al. (1981[Senga, K., Navinson, T. & Wilson, H. R. (1981). J. Med. Chem. 24, 610-613.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10ClN3

  • Mr = 243.69

  • Monoclinic, P 21 /n

  • a = 6.5993 (2) Å

  • b = 12.6166 (4) Å

  • c = 13.8702 (5) Å

  • [beta] = 100.131 (2)°

  • V = 1136.84 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 296 K

  • 0.41 × 0.32 × 0.21 mm

Data collection
  • Bruker X8 APEXII area-detector diffractometer

  • 16957 measured reflections

  • 2925 independent reflections

  • 2521 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.103

  • S = 1.06

  • 2925 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

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: 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5056 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS and CNRST) for the X-ray measurements.

References

Almansa, C. A., Alberto, F., Cavalcanti, F. L., Gomez, L. A., Miralles, A., Merlos, M., Garcia-Rafanell, J. & Forn, J. (2001). J. Med. Chem. 44, 350-361.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, C., Wilcoxen, K. M., Huang, C. Q., Xie, Y.-F., McCarthy, J. R., Webb, T. R., Zhu, Y.-F., Saunders, J., Liu, X.-J., Chen, T.-K., Bozigian, H. & Grigoriadis, D. E. (2004). J. Med. Chem. 47, 4787-4798.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Selleri, S., Gratteri, P., Costagli, C., Bonaccini, C., Costanzo, A., Melani, F., Guerrini, G., Ciciani, G., Costa, B., Spinetti, F., Martini, C. & Bruni, F. (2005). Bioorg. Med. Chem. 13, 4821-4834.  [CrossRef] [PubMed] [ChemPort]
Senga, K., Navinson, T. & Wilson, H. R. (1981). J. Med. Chem. 24, 610-613.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Suzuki, M., Iwasaki, H., Fujikawa, Y., Sakashita, M., Kitahara, M. & Sakoda, R. (2001). Bioorg. Med. Chem. Lett. 11, 1285-1288.  [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o749  [ doi:10.1107/S1600536813009896 ]

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