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Volume 69 
Part 4 
Page o533  
April 2013  

Received 22 February 2013
Accepted 8 March 2013
Online 13 March 2013

Key indicators
Single-crystal X-ray study
T = 110 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.116
Data-to-parameter ratio = 12.9
Details
Open access

6-(3,5-Dimethoxybenzylamino)-9-(oxan-2-yl)-9H-purine

aDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, CZ-771 46 Olomouc, Czech Republic, and bDepartment of Cell Biology and Genetics, Faculty of Science, Palacký University, Slechtitelu 11, CZ-783 71 Olomouc, Czech Republic
Correspondence e-mail: zdenek.travnicek@upol.cz

The molecule of the title compound, C19H23N5O3, contains six-membered pyrimidine and five-membered imidazole rings merged into the essentially planar purine skeleton (r.m.s. deviation = 0.01 Å). In the crystal, pairs of N-H...N hydrogen bonds link molecules into inversion dimers. The dimers are linked via C-H...O hydrogen bonds, forming double-stranded chains propagating along [001]. These chains are linked via C-H...[pi] and parallel slipped [pi]-[pi] interactions [centroid-centroid distance = 3.467 (1) Å; slippage 0.519 Å], forming a three-dimensional network.

Related literature

For the alternative synthetic procedure and biological activity of the title compound, see: Szücová et al. (2009[Szücová, L., Spíchal, L., Dolezal, K., Zatloukal, M., Greplová, J., Galuszka, P., Krystof, V., Voller, J., Popa, I., Massino, F. J., Jørgensen, J. E. & Strnad, M. (2009). Bioorg. Med. Chem. 17, 1938-1947.]). For the structures of similar compounds, see: Soriano-Garcia et al. (2003[Soriano-Garcia, M., Avellaneda, C. R. & Aguirre-Hernandez, G. (2003). Anal. Sci. 19, 1343-1344.]); Taddei et al. (2004[Taddei, D., Kilian, P., Slawin, A. M. Z. & Woollins, J. D. (2004). Org. Biomol. Chem. 2, 665-670.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C19H23N5O3

  • Mr = 369.42

  • Triclinic, [P \overline 1]

  • a = 8.6978 (3) Å

  • b = 8.8318 (3) Å

  • c = 12.1517 (4) Å

  • [alpha] = 84.808 (3)°

  • [beta] = 78.674 (3)°

  • [gamma] = 82.039 (3)°

  • V = 904.53 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 110 K

  • 0.40 × 0.40 × 0.35 mm

Data collection
  • Agilent Xcalibur Sapphire2 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]). Tmin = 0.963, Tmax = 0.968

  • 6684 measured reflections

  • 3177 independent reflections

  • 2784 reflections with I > 2[sigma](I)

  • Rint = 0.010

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.116

  • S = 1.07

  • 3177 reflections

  • 246 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10-C15 ring.

D-H...A D-H H...A D...A D-H...A
N6-H6...N7i 0.88 2.38 3.155 (2) 147
C17-H17A...O3ii 0.98 2.44 3.216 (3) 136
C8-H8...Cgi 0.95 2.72 3.506 (2) 142
C21-H21B...Cgiii 0.99 2.93 3.904 (3) 169
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y, z-1; (iii) -x+2, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, 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: 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: ZQ2196 ).


Acknowledgements

This work was supported by Palacký University (grant No. PrF_2012_009). The authors thank Mr Tomás Silha for performing the CHN elemental analyses.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.
Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Soriano-Garcia, M., Avellaneda, C. R. & Aguirre-Hernandez, G. (2003). Anal. Sci. 19, 1343-1344.  [PubMed] [ChemPort]
Szücová, L., Spíchal, L., Dolezal, K., Zatloukal, M., Greplová, J., Galuszka, P., Krystof, V., Voller, J., Popa, I., Massino, F. J., Jørgensen, J. E. & Strnad, M. (2009). Bioorg. Med. Chem. 17, 1938-1947.  [PubMed]
Taddei, D., Kilian, P., Slawin, A. M. Z. & Woollins, J. D. (2004). Org. Biomol. Chem. 2, 665-670.  [CSD] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o533  [ doi:10.1107/S1600536813006697 ]

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