[Journal logo]

Volume 68 
Part 12 
Pages o3415-o3416  
December 2012  

Received 5 November 2012
Accepted 9 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.093
Data-to-parameter ratio = 16.2
Details
Open access

4,6-Dimethoxy-2-(methylsulfanyl)pyrimidine-4-hydroxybenzoic acid (1/1)

aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Physics, Faculty of Science, University of Mazandaran, Babolsar, Iran, and cDepartment of Chemistry, Government Arts College, Thonthonimalai, Karur, Tamil Nadu, India
Correspondence e-mail: arazaki@usm.my

The base molecule of the title co-crystal, C7H10N2O2S·C7H6O3, is essentially planar, with a maximum deviation of 0.0806 (14) Å for all non-H atoms. The acid molecule is also nearly planar, with a dihedral angle of 8.12 (14)° between the benzene ring and the carboxy group. In the crystal, the acid molecules form an inversion dimer through a pair of O-H...O hydrogen bonds with an R22(8) ring motif. The pyrimidine molecules are linked on both sides of the dimer into a heterotetramer via O-H...N and C-H...O hydrogen bonds with R22(8) ring motifs. The heterotetramers are further linked by weak C-H...O hydrogen bonds, forming a tape structure along [1-10].

Related literature

For general background to substituted pyrimidines, 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.]); Holy et al. (1974[Holy, A., Votruba, I. & Jost, K. (1974). Collect. Czech. Chem. Commun. 39, 634-646.]). For 4-hydroxybenzoic acid, see: Vishweshwar et al. (2003[Vishweshwar, P., Nangia, A. & Lynch, V. M. (2003). CrystEngComm, 5, 164-168.]). For related structures, see: Balasubramani & Fun (2009[Balasubramani, K. & Fun, H.-K. (2009). Acta Cryst. E65, o1895.]); Hemamalini & Fun (2010[Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o294.]). 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
  • C7H10N2O2S·C7H6O3

  • Mr = 324.35

  • Triclinic, [P \overline 1]

  • a = 6.9923 (5) Å

  • b = 10.2887 (8) Å

  • c = 10.7578 (8) Å

  • [alpha] = 77.419 (2)°

  • [beta] = 83.381 (2)°

  • [gamma] = 89.209 (2)°

  • V = 750.27 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 100 K

  • 0.44 × 0.37 × 0.23 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 = 0.901, Tmax = 0.947

  • 13682 measured reflections

  • 3393 independent reflections

  • 3105 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.093

  • S = 1.10

  • 3393 reflections

  • 210 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H1O4...O3i 0.86 (2) 1.76 (2) 2.6189 (14) 172 (3)
O5-H1O5...N1ii 0.80 (3) 1.99 (3) 2.7562 (14) 162 (3)
C9-H9A...O1ii 0.95 2.44 3.3437 (16) 160
C12-H12A...O2iii 0.95 2.59 3.3340 (16) 135
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y-1, z; (iii) x-1, y, z.

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: IS5216 ).


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]
Balasubramani, K. & Fun, H.-K. (2009). Acta Cryst. E65, o1895.  [CSD] [CrossRef] [details]
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.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o294.  [CSD] [CrossRef] [details]
Holy, A., Votruba, I. & Jost, K. (1974). Collect. Czech. Chem. Commun. 39, 634-646.  [ChemPort]
Hunt, W. E., Schwalbe, C. H., Bird, K. & Mallinson, P. D. (1980). J. Biochem. 187, 533-536.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Vishweshwar, P., Nangia, A. & Lynch, V. M. (2003). CrystEngComm, 5, 164-168.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3415-o3416   [ doi:10.1107/S1600536812046338 ]

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.