[Journal logo]

Volume 68 
Part 12 
Pages o3442-o3443  
December 2012  

Received 12 November 2012
Accepted 20 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.101
Data-to-parameter ratio = 11.5
Details
Open access

2,6-Diamino-4-chloropyrimidine-benzoic acid (1/1)

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

The benzoic acid molecule of the title compound, C4H5ClN4·C7H6O2, is approximately planar, with a dihedral angle of 1.28 (9)° between the carboxy group and the benzene ring. In the crystal, two acid and two base molecules are linked through N-H...O and O-H...N hydrogen bonds, forming a centrosymmetric 2 + 2 unit with R22(8) and R42(8) motifs. These units are further linked through a pair of N-H...N hydrogen bonds into a tape structure along [1-20]. The crystal structure also features weak [pi]-[pi] [centroid-centroid distance = 3.5984 (11) Å] and C-H...[pi] interactions.

Related literature

For the biological activity of pyrimidine and aminopyrimidine derivatives, see: Hunt et al. (1980[Hunt, W. E., Schwalbe, C. H., Bird, K. & Mallinson, P. D. (1980). J. Biochem. 187, 533-536.]); Baker & Santi (1965[Baker, B. R. & Santi, D. V. (1965). J. Pharm. Sci. 54, 1252-1257.]). For related structures, see: Schwalbe & Williams (1982[Schwalbe, C. H. & Williams, G. J. B. (1982). Acta Cryst. B38, 1840-1843.]); Hu et al. (2002[Hu, M.-L., Ye, M.-D., Zain, S. M. & Ng, S. W. (2002). Acta Cryst. E58, o1005-o1007.]); Chinnakali et al. (1999[Chinnakali, K., Fun, H.-K., Goswami, S., Mahapatra, A. K. & Nigam, G. D. (1999). Acta Cryst. C55, 399-401.]); Skovsgaard & Bond (2009[Skovsgaard, S. & Bond, A. D. (2009). CrystEngComm, 11, 444-453.]). 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
  • C4H5ClN4·C7H6O2

  • Mr = 266.69

  • Monoclinic, P 21 /c

  • a = 8.7817 (17) Å

  • b = 5.7032 (12) Å

  • c = 24.026 (4) Å

  • [beta] = 95.493 (4)°

  • V = 1197.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 100 K

  • 0.36 × 0.30 × 0.16 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.895, Tmax = 0.951

  • 7539 measured reflections

  • 2097 independent reflections

  • 1891 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.101

  • S = 1.09

  • 2097 reflections

  • 183 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5-C10 ring.

D-H...A D-H H...A D...A D-H...A
O1-H1O1...N2 0.87 (2) 1.74 (2) 2.5976 (18) 168 (3)
N4-H2N4...O2 0.88 (2) 2.03 (2) 2.894 (2) 171.2 (18)
N4-H1N4...O2i 0.88 (2) 2.07 (2) 2.902 (2) 158.2 (19)
N3-H1N3...N1ii 0.85 (2) 2.18 (2) 3.020 (2) 171 (2)
C9-H9A...Cg1iii 0.95 2.99 3.6557 (19) 128
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+2, -z+1; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

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: IS5218 ).


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.  [CrossRef] [ChemPort] [PubMed] [ISI]
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.
Chinnakali, K., Fun, H.-K., Goswami, S., Mahapatra, A. K. & Nigam, G. D. (1999). Acta Cryst. C55, 399-401.  [CSD] [CrossRef] [details]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Hu, M.-L., Ye, M.-D., Zain, S. M. & Ng, S. W. (2002). Acta Cryst. E58, o1005-o1007.  [CSD] [CrossRef] [details]
Hunt, W. E., Schwalbe, C. H., Bird, K. & Mallinson, P. D. (1980). J. Biochem. 187, 533-536.  [ChemPort]
Schwalbe, C. H. & Williams, G. J. B. (1982). Acta Cryst. B38, 1840-1843.  [CrossRef] [ISI] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Skovsgaard, S. & Bond, A. D. (2009). CrystEngComm, 11, 444-453.  [ISI] [CSD] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3442-o3443   [ doi:10.1107/S160053681204768X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.