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Volume 66 
Part 4 
Page o866  
April 2010  

Received 8 March 2010
Accepted 12 March 2010
Online 20 March 2010

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.170
Data-to-parameter ratio = 22.7
Details
Open access

N-Butyl-4-methyl-6-phenylpyrimidin-2-amine

Hoong-Kun Fun,a*+ Wan-Sin Loh,a++ Anita Hazrab and Shyamaprosad Goswamib

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C15H19N3, the pyrimidine ring is approximately planar [maximum deviation = 0.007 (1) Å] and forms a dihedral angle of 3.15 (6)° with the benzene ring. In the crystal packing, intermolecular N-H...N hydrogen bonds link pairs of neighbouring molecules into dimers with R22(8) ring motifs. These dimers are stacked along the b axis.

Related literature

For the biological importance of substituted amino pyrimidines, see: Katrizky (1982[Katrizky, A. R. (1982). J. Chem. Soc. Perkin Trans. 1, pp. 153-158.]); Brown & Lyall (1964[Brown, D. J. & Lyall, M. J. (1964). Aust. J. Chem. 17, 794-802.]); Jonckers et al. (2001[Jonckers, T. H. M., Maes, B. U. W., Lemiere, G. L. F. & Dommisse, R. (2001). Tetrahedron, 57, 7027-7034.]). For their synthesis by microwave processes, see: Goswami et al. (2009[Goswami, S., Hazra, A. & Jana, S. (2009). Bull. Chem. Soc. Jpn, 82, 1175-1181.]). For a related structure, see: Fun et al. (2006[Fun, H.-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006). Acta Cryst. E62, o5332-o5334.]). 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.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C15H19N3

  • Mr = 241.33

  • Monoclinic, P 21 /c

  • a = 13.4828 (9) Å

  • b = 5.1618 (3) Å

  • c = 22.8462 (11) Å

  • [beta] = 123.863 (3)°

  • V = 1320.29 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.30 × 0.23 × 0.08 mm
Data collection

  • Bruker SMART APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.994

  • 13801 measured reflections

  • 3829 independent reflections

  • 3085 reflections with I > 2[sigma](I)

  • Rint = 0.031
Refinement

  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.170

  • S = 1.15

  • 3829 reflections

  • 169 parameters

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

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3B...N2i 0.798 (17) 2.283 (17) 3.0802 (14) 177 (2)
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2745 ).

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks the Malaysian government and USM for the award of Research Fellowship. SG and AH thank the CSIR [No. 01 (2292)/09/ EMR-II], Government of India, for financial support. AH thanks the CSIR, Government of India, for a Research Fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brown, D. J. & Lyall, M. J. (1964). Aust. J. Chem. 17, 794-802.  [CrossRef] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Fun, H.-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006). Acta Cryst. E62, o5332-o5334.  [CSD] [CrossRef] [details]
Goswami, S., Hazra, A. & Jana, S. (2009). Bull. Chem. Soc. Jpn, 82, 1175-1181.  [ISI] [CrossRef] [ChemPort]
Jonckers, T. H. M., Maes, B. U. W., Lemiere, G. L. F. & Dommisse, R. (2001). Tetrahedron, 57, 7027-7034.  [ISI] [CrossRef] [ChemPort]
Katrizky, A. R. (1982). J. Chem. Soc. Perkin Trans. 1, pp. 153-158.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2010). E66, o866  [ doi:10.1107/S1600536810009384 ]

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