4-Chloro-6-meth­oxy­pyrimidin-2-amine–succinic acid (2/1)

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

doi:10.1107/S1600536812046156

Volume 68
Part 12
Page o3343
December 2012

Received 30 October 2012
Accepted 8 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.024
wR = 0.069
Data-to-parameter ratio = 13.4
Details

4-Chloro-6-methoxypyrimidin-2-amine-succinic acid (2/1)

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 asymmetric unit of the title compound, 2C₅H₆ClN₃O·C₄H₆O₄, consists of one 4-chloro-6-methoxypyrimidin-2-amine molecule and one half-molecule of succinic acid which lies about an inversion centre. In the crystal, the acid and base molecules are linked through N-HO and O-HN hydrogen bonds, forming a tape along [1-10] in which R₂²(8) and R₄²(8) hydrogen-bond motifs are observed. The tapes are further interlinked through a pair of C-HO hydrogen bonds into a sheet parallel to (11-2).

Related literature

For applications of pyrimidine derivatives, see: Condon et al. (1993); Maeno et al. (1990); Gilchrist (1997). For applications of succinic acid, see: Zeikus et al. (1999); Song & Lee (2006). 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

2C₅H₆ClN₃O·C₄H₆O₄
M_r = 437.24
Triclinic, $[P \overline 1]$
a = 5.0094 (2) Å
b = 8.5459 (4) Å
c = 10.8736 (5) Å
= 82.337 (1)°
= 88.952 (1)°
= 86.904 (1)°
V = 460.64 (4) Å³
Z = 1
Mo K radiation
= 0.40 mm^-1
T = 100 K
0.60 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.796, T_max = 0.945
7766 measured reflections
1875 independent reflections
1808 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.024
wR(F²) = 0.069
S = 1.09
1875 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.33 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H1N3O3	0.847 (17)	2.223 (17)	3.0055 (13)	153.7 (14)
N3-H2N3O3ⁱ	0.844 (16)	2.095 (16)	2.9369 (13)	175.4 (15)
O2-H1O2N2ⁱ	0.806 (16)	1.923 (16)	2.7266 (13)	174.6 (18)
C3-H3AO1ⁱⁱ	0.95	2.45	3.3911 (14)	172
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+2, -y+1, -z+1.

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: IS5213 ).

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.
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.
Condon, M. E., Brady, T. E., Feist, D., Malefyt, T., Marc, P., Quakenbush, L. S., Rodaway, S. J., Shaner, D. L. & Tecle, B. (1993). Brighton Crop Protection Conference on Weeds, pp. 41-46. Alton, Hampshire, England: BCPC Publications.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Gilchrist, T. L. (1997). Heterocyclic Chemistry, 3rd ed., pp. 261-276. Singapore: Addison Wesley Longman.
Maeno, S., Miura, I., Masuda, K. & Nagata, T. (1990). Brighton Crop Protection Conference on Pests and Diseases, pp. 415-422. Alton, Hampshire, England: BCPC Publications.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, H. & Lee, S. Y. (2006). Enzyme Microb. Technol. 39, 352-361.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zeikus, J. G., Jain, M. K. & Elankovan, P. (1999). Appl. Microbiol. Biotechnol. 51, 545-552.

organic compounds