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Volume 69 
Part 6 
Pages o954-o955  
June 2013  

Received 6 May 2013
Accepted 16 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.058
Data-to-parameter ratio = 13.3
Details
Open access

N-Benzyl-9-isopropyl-9H-purin-6-amine

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

The asymmetric unit of the title compound, C15H17N5, consists of two molecules in which the dihedral angles between the best planes of the purine ring system (r.m.s. deviations = 0.0060 and 0.0190 Å) and the benzene ring are 89.21 (3) and 82.14 (4)°. The molecules within the asymmetric unit are linked into dimers by pairs of N-H...N hydrogen bonds. Weak C-H...[pi] contacts and [pi]-[pi] interactions [centroid-centroid = 3.3071 (1) Å] further connect the molecules into a three-dimensional network.

Related literature

The title compound was prepared according to a modified procedure published by Fiorini & Abel (1998[Fiorini, M. T. & Abel, C. (1998). Tetrahedron Lett. 39, 1827-1830.]). For the biological activity of 6,9-disubstituted purines, see: Cappellacci et al. (2011[Cappellacci, L., Petrelli, R., Franchetti, P., Vita, P., Kusumanchi, P., Kumar, M., Jayram, H. N., Zhou, B., Yen, Y. & Grifantini, M. (2011). Eur. J. Med. Chem. 46, 1499-1504.]); Jorda et al. (2011[Jorda, R., Sacerdoti-Sierra, N., Volle, J., Havlícek, L., Krácalíková, K., Nowicki, M. W., Nasereddin, A., Krystof, V., Strnad, M., Walkinshaw, M. D. & Jaffe, C. L. (2011). Bioorg. Med. Chem. Lett. 21, 4233-4237.]); Tunçbilek et al. (2009[Tunçbilek, M., Ates-Alagöz, Z., Altanlar, N., Karayel, A. & Özbey, S. (2009). Bioorg. Med. Chem. 17, 1693-1700.]). For crystallographic data for related compounds, see: Novotná & Trávnícek (2013[Novotná, R. & Trávnícek, Z. (2013). Acta Cryst. E69, o390.]); 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.]); Trávnícek et al. (2010[Trávnícek, Z., Popa, I., Cajan, M., Zboril, R., Krystof, V. & Mikulík, J. (2010). J. Inorg. Biochem. 104, 405-417.]).

[Scheme 1]

Experimental

Crystal data
  • C15H17N5

  • Mr = 267.34

  • Monoclinic, P 21 /c

  • a = 12.9926 (5) Å

  • b = 21.1673 (7) Å

  • c = 11.2622 (6) Å

  • [beta] = 114.274 (5)°

  • V = 2823.5 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 120 K

  • 0.50 × 0.38 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur (Sapphire2) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.942, Tmax = 1.000

  • 21460 measured reflections

  • 4972 independent reflections

  • 3280 reflections with I > 2[sigma](I)

  • Rint = 0.035

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

  • wR(F2) = 0.058

  • S = 0.83

  • 4972 reflections

  • 373 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are centroids of the C10-C15, C30-C35, N1/N2/C1-C4 and N21/N22/C21-C24 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N5-H5N...N23 0.896 (13) 2.129 (11) 2.9883 (13) 160.2 (12)
N25-H25N...N3 0.908 (12) 2.151 (12) 3.0088 (15) 157.2 (12)
C25-H25...Cg1 0.95 2.76 3.6413 (14) 156
C5-H5...Cg2 0.95 2.72 3.6179 (13) 158
C12-H12...Cg3i 0.95 2.93 3.6703 (17) 135
C15-H15...Cg4ii 0.95 2.60 3.5158 (15) 161
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+2, -y+1, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: PK2482 ).


Acknowledgements

The financial support of this work by the Internal Founding Agency of Tomas Bata University in Zlin (project No. IGA/FT/2013/008) is gratefully acknowledged.

References

Cappellacci, L., Petrelli, R., Franchetti, P., Vita, P., Kusumanchi, P., Kumar, M., Jayram, H. N., Zhou, B., Yen, Y. & Grifantini, M. (2011). Eur. J. Med. Chem. 46, 1499-1504.  [ISI] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fiorini, M. T. & Abel, C. (1998). Tetrahedron Lett. 39, 1827-1830.  [ISI] [CrossRef] [ChemPort]
Jorda, R., Sacerdoti-Sierra, N., Volle, J., Havlícek, L., Krácalíková, K., Nowicki, M. W., Nasereddin, A., Krystof, V., Strnad, M., Walkinshaw, M. D. & Jaffe, C. L. (2011). Bioorg. Med. Chem. Lett. 21, 4233-4237.  [CrossRef] [ChemPort] [PubMed]
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]
Novotná, R. & Trávnícek, Z. (2013). Acta Cryst. E69, o390.  [CrossRef] [details]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Rouchal, M., Necas, M., Carvalho, F. P. de & Vícha, R. (2009a). Acta Cryst. E65, o298-o299.  [CSD] [CrossRef] [ChemPort] [details]
Rouchal, M., Necas, M. & Vícha, R. (2009b). Acta Cryst. E65, o1268.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Trávnícek, Z., Popa, I., Cajan, M., Zboril, R., Krystof, V. & Mikulík, J. (2010). J. Inorg. Biochem. 104, 405-417.  [ISI] [PubMed]
Tunçbilek, M., Ates-Alagöz, Z., Altanlar, N., Karayel, A. & Özbey, S. (2009). Bioorg. Med. Chem. 17, 1693-1700.  [PubMed]


Acta Cryst (2013). E69, o954-o955   [ doi:10.1107/S1600536813013500 ]

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