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Volume 69 
Part 11 
Page o1650  
November 2013  

Received 4 October 2013
Accepted 10 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.112
Data-to-parameter ratio = 22.8
Details
Open access

4-Benzyl­sulfanyl-1H-pyrazolo­[3,4-d]pyrimidine

aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat, Morocco,bLaboratoire National de Contrôle des Médicaments, D M P, Ministère de la Santé, Madinat Al Irnane, BP 6206, Rabat, Morocco, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: elfal_mohammed@yahoo.fr

The pyrazolo­[3,4-d]pyrimidine ring system of the title compound, C12H10N4S, is essentially planar [maximum deviation = 0.025 (1) Å for the C atom bearing the S atom] and almost perpendicular to the phenyl ring [dihedral angle = 71.42 (6)°]. In the crystal, mol­ecules are linked via pairs of N-H...N hydrogen bonds, forming inversion dimers.

Related literature

For the biological properties of pyrazolo­[3,4-d]pyrimidine derivatives, see: Rashad et al. (2008[Rashad, A. E., Hegab, M. I., Abdel-Megeid, R., Micky, J. A. & Abdel-Megeid, F. M. E. (2008). Bioorg. Med. Chem. 16, 7102-7106.], 2011[Rashad, A. E., Abeer, E. M. & Mamdouh, M. A. (2011). Eur. J. Med. Chem. 46, 1019-1026.]); Ballell et al. (2007[Ballell, L., Field, R. A., Chung, G. A. C. & Young, R. J. (2007). Bioorg. Med. Chem. Lett. 17, 1736-1740.]). For related compounds, see: Moussaif et al. (2010[Moussaif, A., Essassi, E. M., Lazar, S., Zouihri, H. & Leger, J. M. (2010). Acta Cryst. E66, o3137.]); Ouzidan et al. (2011[Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822.]); Alsubari et al. (2011[Alsubari, A., Ramli, Y., Essassi, E. M. & Zouihri, H. (2011). Acta Cryst. E67, o1926.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10N4S

  • Mr = 242.30

  • Monoclinic, P 21 /c

  • a = 9.4737 (3) Å

  • b = 5.1709 (2) Å

  • c = 23.6159 (8) Å

  • [beta] = 96.823 (1)°

  • V = 1148.69 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 296 K

  • 0.42 × 0.29 × 0.17 mm

Data collection
  • Bruker X8 APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.991

  • 15333 measured reflections

  • 3509 independent reflections

  • 2885 reflections with I > 2[sigma](I)

  • Rint = 0.029

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

  • wR(F2) = 0.112

  • S = 1.03

  • 3509 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3N...N2i 0.86 2.10 2.9429 (16) 168
Symmetry code: (i) -x+1, -y+2, -z+1.

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: RZ5086 ).


Acknowledgements

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

References

Alsubari, A., Ramli, Y., Essassi, E. M. & Zouihri, H. (2011). Acta Cryst. E67, o1926.  [CSD] [CrossRef] [IUCr Journals]
Ballell, L., Field, R. A., Chung, G. A. C. & Young, R. J. (2007). Bioorg. Med. Chem. Lett. 17, 1736-1740.  [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Moussaif, A., Essassi, E. M., Lazar, S., Zouihri, H. & Leger, J. M. (2010). Acta Cryst. E66, o3137.  [CSD] [CrossRef] [IUCr Journals]
Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822.  [CSD] [CrossRef] [IUCr Journals]
Rashad, A. E., Abeer, E. M. & Mamdouh, M. A. (2011). Eur. J. Med. Chem. 46, 1019-1026.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Rashad, A. E., Hegab, M. I., Abdel-Megeid, R., Micky, J. A. & Abdel-Megeid, F. M. E. (2008). Bioorg. Med. Chem. 16, 7102-7106.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1650  [ doi:10.1107/S160053681302789X ]

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