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Volume 69 
Part 3 
Page o390  
March 2013  

Received 9 February 2013
Accepted 11 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.079
Data-to-parameter ratio = 12.9
Details
Open access

2-Chloro-6-[(2,4-dimethoxybenzyl)amino]-9-isopropyl-9H-purine

aDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, CZ-771 46 Olomouc, Czech Republic
Correspondence e-mail: zdenek.travnicek@upol.cz

In the title compound, C17H20ClN5O2, the benzene ring and the purine ring system make a dihedral angle of 78.56 (4)°. In the crystal, molecules are linked by pairs of N-H...N hydrogen bonds, forming inversion dimers. C-H...O and C-H...Cl contacts further link the molecules, forming a three-dimensional network.

Related literature

For the synthesis, see: Oh et al. (1999[Oh, C. H., Lee, S. C., Lee, K. S., Woo, E. R., Hong, C. Y., Yang, B. S., Baek, D. J. & Cho, J. H. (1999). Arch. Pharm. Pharm. Med. Chem. 332, 187-190.]). For related structures, see: Trávnícek & Popa (2007a[Trávnícek, Z. & Popa, I. (2007a). Acta Cryst. E63, o629-o631.],b[Trávnícek, Z. & Popa, I. (2007b). Acta Cryst. E63, o728-o730.]); Trávnícek et al. (2010[Trávnícek, Z., Popa, I., Cajan, M., Zboril, R., Krystof, V. & Mikulík, J. (2010). J. Inorg. Biochem. 104, 405-417.]); Cajan & Trávnícek (2011[Cajan, M. & Trávnícek, Z. (2011). J. Mol. Struct. 994, 350-359.]). For the cytotoxic activity of related compounds, see: Benson et al. (2005[Benson, C., Kaye, S., Workman, P., Garret, M., Walton, M. & de Bono, J. (2005). Br. J. Cancer, 92, 7-12.]); Meijer et al. (1997[Meijer, L., Borgne, A., Mulner, O., Chong, J. P. J., Blow, J. J., Inagaki, N., Inagaki, M., Delcros, J. G. & Moulinoux, J. P. (1997). Eur. J. Biochem. 243, 527-536.]); Starha et al. (2010[Starha, P., Trávnícek, Z. & Popa, I. (2010). J. Inorg. Biochem. 104, 639-647.]); Vrzal et al. (2010[Vrzal, R., Starha, P., Dvorák, Z. & Trávnícek, Z. (2010). J. Inorg. Biochem. 104, 1130-1132.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20ClN5O2

  • Mr = 361.83

  • Triclinic, [P \overline 1]

  • a = 7.8620 (2) Å

  • b = 9.20164 (18) Å

  • c = 13.3027 (3) Å

  • [alpha] = 82.4472 (18)°

  • [beta] = 74.803 (2)°

  • [gamma] = 66.012 (2)°

  • V = 848.16 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 100 K

  • 0.40 × 0.35 × 0.30 mm

Data collection
  • Agilent Xcalibur Sapphire2 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.908, Tmax = 0.930

  • 7228 measured reflections

  • 2965 independent reflections

  • 2704 reflections with I > 2[sigma](I)

  • Rint = 0.009

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.079

  • S = 1.10

  • 2965 reflections

  • 230 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N6-H6...N7i 0.88 2.16 2.9465 (15) 148
C16-H16C...Cl1ii 0.98 2.78 3.4607 (15) 127
C19-H19A...O2iii 0.98 2.57 3.4709 (17) 154
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z; (iii) x, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and DIAMOND (Brandenburg, 2011[Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: NG5316 ).


Acknowledgements

This work was supported financially by Palacký University (PrF_2012_009). The authors wish to thank Dr Igor Popa for carrying out the NMR spectroscopy measurements and Mr Tomás Silha for performing the CHN elemental analyses.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Benson, C., Kaye, S., Workman, P., Garret, M., Walton, M. & de Bono, J. (2005). Br. J. Cancer, 92, 7-12.  [ISI] [CrossRef] [PubMed] [ChemPort]
Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cajan, M. & Trávnícek, Z. (2011). J. Mol. Struct. 994, 350-359.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Meijer, L., Borgne, A., Mulner, O., Chong, J. P. J., Blow, J. J., Inagaki, N., Inagaki, M., Delcros, J. G. & Moulinoux, J. P. (1997). Eur. J. Biochem. 243, 527-536.  [CrossRef] [ChemPort] [PubMed] [ISI]
Oh, C. H., Lee, S. C., Lee, K. S., Woo, E. R., Hong, C. Y., Yang, B. S., Baek, D. J. & Cho, J. H. (1999). Arch. Pharm. Pharm. Med. Chem. 332, 187-190.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Starha, P., Trávnícek, Z. & Popa, I. (2010). J. Inorg. Biochem. 104, 639-647.  [ISI] [PubMed]
Trávnícek, Z. & Popa, I. (2007a). Acta Cryst. E63, o629-o631.  [CSD] [CrossRef] [details]
Trávnícek, Z. & Popa, I. (2007b). Acta Cryst. E63, o728-o730.  [CSD] [CrossRef] [details]
Trávnícek, Z., Popa, I., Cajan, M., Zboril, R., Krystof, V. & Mikulík, J. (2010). J. Inorg. Biochem. 104, 405-417.  [ISI] [PubMed]
Vrzal, R., Starha, P., Dvorák, Z. & Trávnícek, Z. (2010). J. Inorg. Biochem. 104, 1130-1132.  [ISI] [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o390  [ doi:10.1107/S1600536813004121 ]

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