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

Thanigaimani, K.; Farhadikoutenaei, A.; Arshad, S.; Razak, I.A.; Balasubramani, K.

doi:10.1107/S1600536812046338

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 (C-C) = 0.002 Å
R = 0.032
wR = 0.093
Data-to-parameter ratio = 16.2
Details

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

Kaliyaperumal Thanigaimani,^a Abbas Farhadikoutenaei,^a,^b Suhana Arshad,^a Ibrahim Abdul Razak ^a ^*⁺ and Kasthuri Balasubramani ^c

^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-HO hydrogen bonds with an R₂²(8) ring motif. The pyrimidine molecules are linked on both sides of the dimer into a heterotetramer via O-HN and C-HO hydrogen bonds with R₂²(8) ring motifs. The heterotetramers are further linked by weak C-HO hydrogen bonds, forming a tape structure along [1-10].

Related literature

For general background to substituted pyrimidines, see: Hunt et al. (1980); Baker & Santi (1965); Holy et al. (1974). For 4-hydroxybenzoic acid, see: Vishweshwar et al. (2003). For related structures, see: Balasubramani & Fun (2009); Hemamalini & Fun (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₇H₁₀N₂O₂S·C₇H₆O₃
M_r = 324.35
Triclinic, $[P \overline 1]$
a = 6.9923 (5) Å
b = 10.2887 (8) Å
c = 10.7578 (8) Å
= 77.419 (2)°
= 83.381 (2)°
= 89.209 (2)°
V = 750.27 (10) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.901, T_max = 0.947
13682 measured reflections
3393 independent reflections
3105 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(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
_max = 0.46 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H1O4O3ⁱ	0.86 (2)	1.76 (2)	2.6189 (14)	172 (3)
O5-H1O5N1ⁱⁱ	0.80 (3)	1.99 (3)	2.7562 (14)	162 (3)
C9-H9AO1ⁱⁱ	0.95	2.44	3.3437 (16)	160
C12-H12AO2ⁱⁱⁱ	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); 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: 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.
Balasubramani, K. & Fun, H.-K. (2009). Acta Cryst. E65, o1895.
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.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o294.
Holy, A., Votruba, I. & Jost, K. (1974). Collect. Czech. Chem. Commun. 39, 634-646.
Hunt, W. E., Schwalbe, C. H., Bird, K. & Mallinson, P. D. (1980). J. Biochem. 187, 533-536.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vishweshwar, P., Nangia, A. & Lynch, V. M. (2003). CrystEngComm, 5, 164-168.

organic compounds