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Volume 69 
Part 5 
Page o698  
May 2013  

Received 3 April 2013
Accepted 8 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.078
Data-to-parameter ratio = 13.4
Details
Open access

N-Benzylthieno[3,2-d]pyrimidin-4-amine

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

The title compound, C13H11N3S, crystallizes with two independent molecules in the asymmetric unit. The two molecules are geometrically very similar and differ mainly in a spatial orientation of the benzene and thieno[3,2-d]pyrimidine ring systems [dihedral angles = 69.49 (4) and 79.05 (3)°]. The nine-membered thieno[3,2-d]pyrimidine moieties have a planar conformation (r.m.s. deviations = 0.020 and 0.012 Å). In the crystal, molecules are linked through N-H...N, N-H...C and C-H...[pi] non-covalent contacts into chains along the c axis, while neighbouring chains are connected via C-H...N interactions.

Related literature

For the synthesis of 4-benzylaminothieno[3,2-d]pyrimidine hydrochloride, its NMR characterization (DMSO-d6 solution) and biological activity, see: Crespo et al. (1998[Crespo, M. I., Pagés, L., Vega, A., Segarra, V., López, M., Doménech, T., Miralpeix, M., Beleta, J., Ryder, H. & Palacios, J. M. (1998). J. Med. Chem. 41, 4021-4035.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11N3S

  • Mr = 241.31

  • Monoclinic, P 21 /c

  • a = 19.3430 (4) Å

  • b = 9.46296 (16) Å

  • c = 12.8221 (2) Å

  • [beta] = 94.3231 (17)°

  • V = 2340.30 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 120 K

  • 0.40 × 0.40 × 0.25 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 = 0.905, Tmax = 0.939

  • 19406 measured reflections

  • 4109 independent reflections

  • 3528 reflections with I > 2[sigma](I)

  • Rint = 0.019

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

  • wR(F2) = 0.078

  • S = 1.07

  • 4109 reflections

  • 307 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.25 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
N4-H4...N1i 0.88 2.13 2.999 (2) 167
N4A-H4A...N1Aii 0.88 2.05 2.872 (2) 156
C7-H7...Cgiii 0.95 2.58 3.5317 (13) 175
C2A-H2A...N3iv 0.95 2.67 3.527 (2) 150
C15-H15...N3A 0.95 2.58 3.4842 (18) 159
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [x, -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: TK5215 ).


Acknowledgements

This work was supported by Palacký University (grant No. PrF_2013_015). The authors wish to thank Dr Igor Popa for performing NMR experiments and Mr Tomás Silha for performing CHN elemental analysis.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Crespo, M. I., Pagés, L., Vega, A., Segarra, V., López, M., Doménech, T., Miralpeix, M., Beleta, J., Ryder, H. & Palacios, J. M. (1998). J. Med. Chem. 41, 4021-4035.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o698  [ doi:10.1107/S1600536813009537 ]

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