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Volume 69 
Part 2 
Page o197  
February 2013  

Received 14 December 2012
Accepted 16 December 2012
Online 9 January 2013

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.051
wR = 0.171
Data-to-parameter ratio = 12.0
Details
Open access

4-Methyl-6-(piperidin-1-yl)pyrimidin-2-amine

S. Sreenivasa,a* K. E. ManojKumar,a T. Srinivasan,b P. A. Suchetan,c B. S. Palakshamurthyd and D. Velumurganb

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bCentre of Advanced Study in Crystallography and Biophysics, University of Madras Guindy Campus, Chennai 600 025, India,cDepartment of Studies and Research in Chemistry, U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India, and dDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

The title compound, C10H16N4, crystalizes with two molecules (A and B) in the asymmetric unit in which the dihedral angles between the piperidine and pyrimidine rings are 47.5 (1) and 10.3 (1)°. The four C atoms of the pyrimidine ring in one of the molecules are disordered over two sets of sites with occupancy factors 0.508 (11):0.492 (11). In the crystal, the A molecules are linked to one another through N-H...N hydrogen bonds, generating R22(8) ring patterns and forming inversion dimers. These dimers are further connected on either side to a B molecule through pairs of N-H...N hydrogen bonds, resulting in a tetrameric unit.

Related literature

For background to pyrimidine derivatives and their biological activity, see: Patel et al. (2003[Patel, R., Desai, K. & Chikhalia, K. (2003). J. Indian Chem. Soc. 80, 138-145.]) and for a related structure see: Sreenivasa et al. (2012[Sreenivasa, S., ManojKumar, K. E., Suchetan, P. A., Srinivasan, T., Palakshamurthy, B. S. & Velmurgan, D. (2012). Acta Cryst. E68, o3371.]). For hydrogen bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C10H16N4

  • Mr = 192.27

  • Monoclinic, P 21 /n

  • a = 13.9605 (4) Å

  • b = 8.7564 (3) Å

  • c = 17.7055 (6) Å

  • [beta] = 104.381 (2)°

  • V = 2096.57 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.24 × 0.22 × 0.20 mm
Data collection

  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.985

  • 15644 measured reflections

  • 3708 independent reflections

  • 2657 reflections with I > 2[sigma](I)

  • Rint = 0.027
Refinement

  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.171

  • S = 1.10

  • 3708 reflections

  • 308 parameters

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-HN3B...N1i 0.86 (2) 2.19 (2) 3.043 (2) 173.3 (19)
N3-HN3A...N5 0.90 (2) 2.34 (2) 3.210 (2) 162.1 (17)
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5288 ).

Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, for his constant encouragement. BSP thanks Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his support and guidence.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Patel, R., Desai, K. & Chikhalia, K. (2003). J. Indian Chem. Soc. 80, 138-145.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sreenivasa, S., ManojKumar, K. E., Suchetan, P. A., Srinivasan, T., Palakshamurthy, B. S. & Velmurgan, D. (2012). Acta Cryst. E68, o3371.  [CSD] [CrossRef] [details]

Acta Cryst (2013). E69, o197  [ doi:10.1107/S1600536812050982 ]

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