[Journal logo]

Volume 68 
Part 6 
Page o1585  
June 2012  

Received 16 April 2012
Accepted 26 April 2012
Online 2 May 2012

[lh5458sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.023
wR = 0.061
Data-to-parameter ratio = 12.8
Details
Open access

2,6-Dichloro-7-isopropyl-7H-purine

Nikola Hlousková,a Michal Rouchal,a Marek Necasb and Robert Víchaa*

aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín, 762 72, Czech Republic, and bDepartment of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
Correspondence e-mail: rvicha@ft.utb.cz

In the title molecule, C8H8Cl2N4, the essentially planar imidazole and pyrimidine rings [maximum deviations of 0.0030 (15) and 0.0111 (15) Å, respectively] make a dihedral angle of 1.32 (8)°. In the crystal, the fused-ring systems are stacked approximately parallel to the bc plane, with a centroid-centroid distance between inversion-related pyrimidine rings of 3.5189 (9) Å.

Related literature

For the synthesis, see: Oumata et al. (2008[Oumata, M., Bettayeb, K., Ferandin, Y., Demange, L., Lopez-Giral, A., Goddard, M.-L., Myrianthopoulos, V., Mikros, E., Flajolet, M., Greengard, P., Meijer, L. & Galons, H. (2008). J. Med. Chem. 51, 5229-5242.]). For biological activity of some purine derivatives, see: Legraverend & Grierson (2006[Legraverend, M. & Grierson, D. S. (2006). Bioorg. Med. Chem. 14, 3987-4006.]). For the selective synthesis of N7-substituted purines, see: Kotek et al. (2010[Kotek, V., Chudíková, N., Tobrman, T. & Dvorák, D. (2010). Org. Lett. 12, 5724-5727.]). For related structures, see: Rouchal et al. (2009a[Rouchal, M., Necas, M., Carvalho, F. P. de & Vícha, R. (2009a). Acta Cryst. E65, o298-o299.],b[Rouchal, M., Necas, M. & Vícha, R. (2009b). Acta Cryst. E65, o1268.], 2010[Rouchal, M., Necas, M. & Vícha, R. (2010). Acta Cryst. E66, o1016.]).

[Scheme 1]

Experimental

Crystal data

  • C8H8Cl2N4

  • Mr = 231.08

  • Triclinic, [P \overline 1]

  • a = 7.0146 (5) Å

  • b = 8.2862 (6) Å

  • c = 8.9686 (7) Å

  • [alpha] = 70.499 (7)°

  • [beta] = 83.820 (6)°

  • [gamma] = 74.204 (6)°

  • V = 472.75 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.65 mm-1

  • T = 120 K

  • 0.40 × 0.40 × 0.20 mm
Data collection

  • Oxford Diffraction Xcalibur Sapphire2 diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.933, Tmax = 1.000

  • 2825 measured reflections

  • 1656 independent reflections

  • 1419 reflections with I > 2[sigma](I)

  • Rint = 0.011
Refinement

  • R[F2 > 2[sigma](F2)] = 0.023

  • wR(F2) = 0.061

  • S = 1.05

  • 1656 reflections

  • 129 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]); 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5458 ).

Acknowledgements

The financial support of this work by the Internal Founding Agency of Tomas Bata University in Zlin (project No. IGA/FT/2012/016) is gratefully acknowledged.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kotek, V., Chudíková, N., Tobrman, T. & Dvorák, D. (2010). Org. Lett. 12, 5724-5727.  [ISI] [CrossRef] [ChemPort] [PubMed]
Legraverend, M. & Grierson, D. S. (2006). Bioorg. Med. Chem. 14, 3987-4006.  [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Oumata, M., Bettayeb, K., Ferandin, Y., Demange, L., Lopez-Giral, A., Goddard, M.-L., Myrianthopoulos, V., Mikros, E., Flajolet, M., Greengard, P., Meijer, L. & Galons, H. (2008). J. Med. Chem. 51, 5229-5242.  [ISI] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.
Rouchal, M., Necas, M., Carvalho, F. P. de & Vícha, R. (2009a). Acta Cryst. E65, o298-o299.  [CSD] [CrossRef] [details]
Rouchal, M., Necas, M. & Vícha, R. (2009b). Acta Cryst. E65, o1268.  [CSD] [CrossRef] [details]
Rouchal, M., Necas, M. & Vícha, R. (2010). Acta Cryst. E66, o1016.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2012). E68, o1585  [ doi:10.1107/S160053681201879X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.