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

Novotná, R.; Trávníček, Z.

doi:10.1107/S1600536813004121

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 (C-C) = 0.002 Å
R = 0.029
wR = 0.079
Data-to-parameter ratio = 12.9
Details

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

Radka Novotná ^a and Zdenek Trávnícek ^a ^*

^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-HN hydrogen bonds, forming inversion dimers. C-HO and C-HCl contacts further link the molecules, forming a three-dimensional network.

Related literature

For the synthesis, see: Oh et al. (1999). For related structures, see: Trávnícek & Popa (2007a,b); Trávnícek et al. (2010); Cajan & Trávnícek (2011). For the cytotoxic activity of related compounds, see: Benson et al. (2005); Meijer et al. (1997); Starha et al. (2010); Vrzal et al. (2010).

Experimental

Crystal data

C₁₇H₂₀ClN₅O₂
M_r = 361.83
Triclinic, $[P \overline 1]$
a = 7.8620 (2) Å
b = 9.20164 (18) Å
c = 13.3027 (3) Å
= 82.4472 (18)°
= 74.803 (2)°
= 66.012 (2)°
V = 848.16 (3) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.908, T_max = 0.930
7228 measured reflections
2965 independent reflections
2704 reflections with I > 2(I)
R_int = 0.009

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.079
S = 1.10
2965 reflections
230 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N6-H6N7ⁱ	0.88	2.16	2.9465 (15)	148
C16-H16CCl1ⁱⁱ	0.98	2.78	3.4607 (15)	127
C19-H19AO2ⁱⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and DIAMOND (Brandenburg, 2011); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
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.
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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Starha, P., Trávnícek, Z. & Popa, I. (2010). J. Inorg. Biochem. 104, 639-647.
Trávnícek, Z. & Popa, I. (2007a). Acta Cryst. E63, o629-o631.
Trávnícek, Z. & Popa, I. (2007b). Acta Cryst. E63, o728-o730.
Trávnícek, Z., Popa, I., Cajan, M., Zboril, R., Krystof, V. & Mikulík, J. (2010). J. Inorg. Biochem. 104, 405-417.
Vrzal, R., Starha, P., Dvorák, Z. & Trávnícek, Z. (2010). J. Inorg. Biochem. 104, 1130-1132.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds