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Volume 69 
Part 5 
Page o740  
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) = 0.003 Å
R = 0.052
wR = 0.170
Data-to-parameter ratio = 14.6
Details
Open access

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

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 Nanomaterials 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, C16H15N3O2, are almost coplanar, being inclined to one another by 1.31 (12)°. The mean plane of this fused ring system is nearly coplanar with the phenyl ring, as indicated by the dihedral angle between their planes of 1.31 (12)°. The fused-ring system and the phenyl ring are nearly coplanar, as indicated by the dihedral angle of 1.27 (10)°. In the crystal, molecules form inversion dimers via pairs of C-H...O hydrogen bonds. C-H...N interactions connect the dimers into a three-dimensional network. In addition, [pi]-[pi] contacts are observed, with centroid-centroid distances of 3.426 (2) Å.

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: Chimichi et al. (1992[Chimichi, S., Cosimelli, B., Bruni, F. & Selleri, S. (1992). Magn. Reson. Chem. 30, 1117-1121.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15N3O2

  • Mr = 281.31

  • Orthorhombic, P b c a

  • a = 8.0542 (8) Å

  • b = 16.4104 (19) Å

  • c = 21.635 (2) Å

  • V = 2859.5 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.41 × 0.32 × 0.21 mm

Data collection
  • Bruker X8 APEXII area-detector diffractometer

  • 12894 measured reflections

  • 2783 independent reflections

  • 1919 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.170

  • S = 1.04

  • 2783 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12...O1i 0.93 2.36 3.258 (3) 161
C6-H6...N3ii 0.93 2.62 3.507 (3) 161
Symmetry codes: (i) -x+2, -y+1, -z; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

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: 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: RZ5057 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, 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 and SAINT. 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]
Chimichi, S., Cosimelli, B., Bruni, F. & Selleri, S. (1992). Magn. Reson. Chem. 30, 1117-1121.  [CrossRef] [ChemPort] [ISI]
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]
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, o740  [ doi:10.1107/S1600536813009902 ]

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