2-{[4-(Pyridin-2-yl)pyrimidin-2-yl]sulfan­yl}acetic acid

Lin Wang; Hua-Ze Dong

doi:10.1107/S1600536811039791

. 2011 Oct 12;67(Pt 11):o2916. doi: 10.1107/S1600536811039791

2-{[4-(Pyridin-2-yl)pyrimidin-2-yl]sulfanyl}acetic acid

Lin Wang ^a, Hua-Ze Dong ^a,^*

PMCID: PMC3247330 PMID: 22219948

Abstract

In the title molecule, C₁₁H₉N₃O₂S, the pyridine and pyrimidine rings are almost parallel [dihedral angle = 6.7 (1)°]. In the crystal, adjacent molecules are joined by O—H⋯N and C—H⋯O hydrogen bonds, leading to the formation of a sheet parallel to (10 Inline graphic ).

Related literature

For details of the synthesis and general background, see: Dong et al. (2009 ▶); Wang (2011 ▶). For the crystal structures of coordination complexes with related ligands, see: Du et al. (2004 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C₁₁H₉N₃O₂S
M _r = 247.28
Monoclinic,
a = 6.5722 (2) Å
b = 22.4650 (8) Å
c = 7.4314 (2) Å
β = 93.237 (2)°
V = 1095.45 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 291 K
0.28 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.920, T _max = 0.950
10868 measured reflections
2524 independent reflections
2116 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.096
S = 1.05
2524 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039791/kj2186sup1.cif

e-67-o2916-sup1.cif^{(14.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039791/kj2186Isup2.hkl

e-67-o2916-Isup2.hkl^{(124KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039791/kj2186Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2ⁱ	0.82	1.87	2.694 (2)	178
C2—H2A⋯O1ⁱⁱ	0.93	2.58	3.230 (2)	127
C8—H8⋯O2ⁱⁱⁱ	0.93	2.48	3.392 (2)	165
C9—H9⋯O1^iv	0.93	2.45	3.296 (2)	151

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

This work was supported by the National Science Foundation of China (No. 20871039), the Program for Excellent Young Talents in Universities of Anhui Province (2011SQRL128) and the Science Foundation of Hefei Normal University(2010kj01zd).

supplementary crystallographic information

Comment

The rational dsign and assembly of new coordination polymers with with thioethers derived from 4-pyridinyl pyrimidine-2-thiol have received considerable attention in recent years (Dong et al., 2009; Du et al., 2004; Wang, 2011; Zhu et al., 2009). Here we report the crystal structure of a newly synthesized compound derived from 4-(4-pyridinyl)pyrimidine-2-thiol.

The molecular structure of title compound is shown in Fig. 1 together with the atom-numbering scheme. The pyridine and pyrimidine rings are almost parallel with a dihedral angle of 6.7 (1)°. Molecules are linked by O-H···N hydrogen bonds into a chain running in direction [2 0 1]. C-H···O interactions join these chains into a two-dimensional network with base vectors [2 0 1] and [0 1 0] (equivalent to a sheet parallel to the (1 0 -2) lattice planes). Geometrical details are given in Table 1; a plot is given in Fig. 2.

Experimental

All solvents and chemicals were of analytical grade and were used without further purification. The title compound was prepared by a similar procedure as reported in the literature (Dong et al., 2009). To a solution of 4-(4-pyridinyl)pyrimidine-2-thiol (3.78 g, 20 mmol) and sodium hydroxide (0.80 g, 20 mmol) in water (30 ml), 2-bromoacetic acid (2.78 g, 20 mmol) in water (30 ml) was added. The mixture was stirred at room temperature for 4 h. Dilute hydrochloric acid was added to the reacted solution until the pH was about 4. Precipitates were filtered, washed by water and ethanol, and dried in vacuum. Single crystals suitable for X-ray diffraction were grown from a methanol solution by slow evaporation in air at room temperature.