4-Chloro-6-meth­oxy­pyrimidin-2-amine

Thanigaimani, K.; Khalib, N.C.; Arshad, S.; Razak, I.A.

doi:10.1107/S160053681204528X

Volume 68
Part 12
Page o3318
December 2012

Received 30 October 2012
Accepted 2 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.027
wR = 0.070
Data-to-parameter ratio = 24.4
Details

4-Chloro-6-methoxypyrimidin-2-amine

Kaliyaperumal Thanigaimani,^a Nuridayanti Che Khalib,^a Suhana Arshad ^a and Ibrahim Abdul Razak ^a ^*⁺

^aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

The title compound, C₅H₆ClN₃O, is essentially planar with a maximum deviation of 0.0256 (11) Å for all non-H atoms. In the crystal, adjacent molecules are linked by a pair of N-HN hydrogen bonds, forming an inversion dimer with an R₂²(8) ring motif. The dimers are further linked via N-HO hydrogen bonds into an undulating sheet structure parallel to the bc plane.

Related literature

For the biological activity of pyrimidine and aminopyrimidine derivatives, see: Hunt et al. (1980); Baker & Santi (1965). For related structures, see: Schwalbe & Williams (1982); Hu et al. (2002); Chinnakali et al. (1999); Skovsgaard & Bond (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₅H₆ClN₃O
M_r = 159.58
Monoclinic, P 2₁ /c
a = 3.7683 (2) Å
b = 16.4455 (2) Å
c = 10.7867 (2) Å
= 94.550 (1)°
V = 666.36 (4) Å³
Z = 4
Mo K radiation
= 0.50 mm^-1
T = 100 K
0.49 × 0.28 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.791, T_max = 0.904
9524 measured reflections
2436 independent reflections
2266 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.070
S = 1.06
2436 reflections
100 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.67 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H2N3O1ⁱ	0.828 (16)	2.251 (17)	3.0699 (11)	170.1 (15)
N3-H1N3N1ⁱⁱ	0.850 (16)	2.183 (16)	3.0335 (12)	180 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5214 ).

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171 to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS-USM 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.
Baker, B. R. & Santi, D. V. (1965). J. Pharm. Sci. 54, 1252-1257.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chinnakali, K., Fun, H.-K., Goswami, S., Mahapatra, A. K. & Nigam, G. D. (1999). Acta Cryst. C55, 399-401.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Hu, M.-L., Ye, M.-D., Zain, S. M. & Ng, S. W. (2002). Acta Cryst. E58, o1005-o1007.
Hunt, W. E., Schwalbe, C. H., Bird, K. & Mallinson, P. D. (1980). J. Biochem. 187, 533-536.
Schwalbe, C. H. & Williams, G. J. B. (1982). Acta Cryst. B38, 1840-1843.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Skovsgaard, S. & Bond, A. D. (2009). CrystEngComm, 11, 444-453.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds