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Volume 69 
Part 6 
Page o829  
June 2013  

Received 23 April 2013
Accepted 30 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.107
Data-to-parameter ratio = 25.2
Details
Open access

N-(2-Bromo-4-methylphenyl)-2-(5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-yl)acetamide

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, C22H19BrN4O, are almost coplanar, their planes being inclined to one another by 2.08 (13)°. The dihedral angles formed by the mean plane of the fused ring system and the phenyl and benzene rings are 16.21 (4) and 82.84 (4)°, respectively. An intramolecular N-H...N hydrogen bond is observed. In the crystal, molecules form inversion dimers via pairs of C-H...O hydrogen bonds. [pi]-[pi] interactions, with centroid-centroid distances of 3.4916 (9) Å, connect the dimers into a three-dimensional network.

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: Bassoude et al. (2013a[Bassoude, I., Berteina-Raboin, S., Essassi, E. M., Guillaumet, G. & El Ammari, L. (2013a). Acta Cryst. E69, o740.],b[Bassoude, I., Berteina-Raboin, S., Essassi, E. M., Guillaumet, G. & El Ammari, L. (2013b). Acta Cryst. E69, o749.]).

[Scheme 1]

Experimental

Crystal data
  • C22H19BrN4O

  • Mr = 435.32

  • Monoclinic, P 21 /c

  • a = 9.8102 (6) Å

  • b = 7.2915 (4) Å

  • c = 27.0162 (14) Å

  • [beta] = 92.942 (3)°

  • V = 1929.95 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.15 mm-1

  • T = 296 K

  • 0.42 × 0.33 × 0.25 mm

Data collection
  • Bruker X8 APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.739, Tmax = 0.867

  • 29996 measured reflections

  • 6371 independent reflections

  • 3830 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.107

  • S = 1.02

  • 6371 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.62 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4A...N2 0.86 2.17 2.927 (2) 147
C14-H14...O1i 0.93 2.43 3.189 (2) 139
Symmetry code: (i) -x+2, -y+1, -z.

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: RZ5060 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray diffraction 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]
Bassoude, I., Berteina-Raboin, S., Essassi, E. M., Guillaumet, G. & El Ammari, L. (2013a). Acta Cryst. E69, o740.  [CrossRef] [details]
Bassoude, I., Berteina-Raboin, S., Essassi, E. M., Guillaumet, G. & El Ammari, L. (2013b). Acta Cryst. E69, o749.  [CrossRef] [details]
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]
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, o829  [ doi:10.1107/S1600536813011811 ]

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