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Volume 69 
Part 4 
Page o588  
April 2013  

Received 19 March 2013
Accepted 20 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 110 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.087
Data-to-parameter ratio = 12.5
Details
Open access

N-(2-Methoxybenzyl)-9-(oxolan-2-yl)-9H-purin-6-amine

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 title compound, C17H19N5O2, features an almost planar purine skeleton (r.m.s. deviation = 0.009 Å) substituted by a tetrahydrofuran ring, which adopts an envelope conformation. The purine and benzene rings subtend a dihedral angle of 66.70 (3)°. In the crystal, pairs of N-H...N hydrogen bonds connect adjacent molecules into inversion dimers. C-H...N, C-H...O, C-H...[pi] and [pi]-[pi] interactions [pyrimidine ring centroid-centroid distance = 3.3909 (1) Å] connect the dimers into a three-dimensional architecture.

Related literature

For an alternative synthetic procedure and the biological activity of benzyl-substituted 6-benzylamino-9-tetrahydropyran-2-yl-9H-purine derivatives, 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 a related structure, see: Starha et al. (2013[Starha, P., Popa, I., Dvorák, Z. & Trávnícek, Z. (2013). Acta Cryst. E69, o533.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19N5O2

  • Mr = 325.37

  • Monoclinic, P 21 /n

  • a = 8.87210 (19) Å

  • b = 8.37534 (17) Å

  • c = 20.7445 (4) Å

  • [beta] = 90.4360 (19)°

  • V = 1541.42 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 110 K

  • 0.35 × 0.30 × 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 = 0.967, Tmax = 0.972

  • 12687 measured reflections

  • 2719 independent reflections

  • 2415 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.087

  • S = 1.04

  • 2719 reflections

  • 218 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, °)

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 2.32 3.145 (2) 157
C8-H8...Cgi 0.95 2.86 3.6214 (14) 138
C12-H12...O2ii 0.95 2.60 3.459 (2) 150
C13-H13...N3ii 0.95 2.55 3.489 (2) 170
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

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: 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: NG5319 ).


Acknowledgements

This work was supported by Palacký University (grant No. PrF_2013_015). The authors wish to thank Mr Tomás Silha for performing the CHN elemental analysis.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Starha, P., Popa, I., Dvorák, Z. & Trávnícek, Z. (2013). Acta Cryst. E69, o533.  [CrossRef] [details]
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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o588  [ doi:10.1107/S1600536813007721 ]

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