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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 [sigma](C-C) = 0.002 Å
R = 0.024
wR = 0.069
Data-to-parameter ratio = 13.4
Details
Open access

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

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-H...O and O-H...N 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-H...O hydrogen bonds into a sheet parallel to (11-2).

Related literature

For applications of pyrimidine derivatives, see: Condon et al. (1993[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.]); Maeno et al. (1990[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.]); Gilchrist (1997[Gilchrist, T. L. (1997). Heterocyclic Chemistry, 3rd ed., pp. 261-276. Singapore: Addison Wesley Longman.]). For applications of succinic acid, see: Zeikus et al. (1999[Zeikus, J. G., Jain, M. K. & Elankovan, P. (1999). Appl. Microbiol. Biotechnol. 51, 545-552.]); Song & Lee (2006[Song, H. & Lee, S. Y. (2006). Enzyme Microb. Technol. 39, 352-361.]). 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 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
  • 2C5H6ClN3O·C4H6O4

  • Mr = 437.24

  • Triclinic, [P \overline 1]

  • a = 5.0094 (2) Å

  • b = 8.5459 (4) Å

  • c = 10.8736 (5) Å

  • [alpha] = 82.337 (1)°

  • [beta] = 88.952 (1)°

  • [gamma] = 86.904 (1)°

  • V = 460.64 (4) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.796, Tmax = 0.945

  • 7766 measured reflections

  • 1875 independent reflections

  • 1808 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H1N3...O3 0.847 (17) 2.223 (17) 3.0055 (13) 153.7 (14)
N3-H2N3...O3i 0.844 (16) 2.095 (16) 2.9369 (13) 175.4 (15)
O2-H1O2...N2i 0.806 (16) 1.923 (16) 2.7266 (13) 174.6 (18)
C3-H3A...O1ii 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[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. 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: 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.  [CrossRef] [ChemPort] [ISI]
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.  [CrossRef] [ChemPort] [ISI] [details]
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.  [CrossRef] [details]
Song, H. & Lee, S. Y. (2006). Enzyme Microb. Technol. 39, 352-361.  [ISI] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zeikus, J. G., Jain, M. K. & Elankovan, P. (1999). Appl. Microbiol. Biotechnol. 51, 545-552.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3343  [ doi:10.1107/S1600536812046156 ]

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