Ethyl 2-{[4-(pyridin-4-yl)pyrimidin-2-yl]sulfan­yl}acetate

Chuan-Hu Wang

doi:10.1107/S1600536811004272

. 2011 Feb 23;67(Pt 3):o690. doi: 10.1107/S1600536811004272

Ethyl 2-{[4-(pyridin-4-yl)pyrimidin-2-yl]sulfanyl}acetate

Chuan-Hu Wang ^a,^*

PMCID: PMC3052020 PMID: 21522435

Abstract

In the title molecule, C₁₃H₁₃N₃O₂S, the pyridine and pyrimidine rings form a dihedral angle of 3.8 (1)°. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For details of the synthesis and general background to the rational design and assembly of coordination polymers with thioethers, see: Dong et al. (2008 ▶, 2009 ▶). For the crystal structures of coordination complexes with related ligands, see: Du et al. (2004 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C₁₃H₁₃N₃O₂S
M _r = 275.33
Triclinic,
a = 8.6579 (8) Å
b = 9.7394 (9) Å
c = 9.9188 (8) Å
α = 62.661 (6)°
β = 71.416 (5)°
γ = 65.024 (6)°
V = 665.35 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 291 K
0.32 × 0.24 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.917, T _max = 0.966
11760 measured reflections
3021 independent reflections
2387 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.115
S = 1.04
3021 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 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 datablocks I, global. DOI: 10.1107/S1600536811004272/cv5047sup1.cif

e-67-0o690-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004272/cv5047Isup2.hkl

e-67-0o690-Isup2.hkl^{(148.2KB, hkl)}

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
C3—H3⋯O1ⁱ	0.93	2.52	3.383 (2)	154
C7—H7⋯O1ⁱⁱ	0.93	2.61	3.373 (2)	140

Open in a new tab

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

Acknowledgments

The author is indebted to the National Natural Science Foundation of China (grant No. 20871039) for financial support.

supplementary crystallographic information

Comment

Remarkable attention has been paid to the rational design and assembly of new coordination polymers with thioethers (Dong et al., 2008; 2009; Du et al., 2004; Zhu et al., 2009). Herewith we report the synthesis and crystal structure of the title compound (I)- a new derivative of 4-(4-pyridinyl)pyrimidine-2-thiol.

In (I) (Fig. 1), the pyridine and pyrimidine rings form a dihedral angle of 3.8 (1)°. The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

All solvents and chemicals were of analytical grade and were used without further purification. The title compound was prepared by similar procedure reported in the literature (Dong et al., 2008; 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 dry ethanol (100 ml), ethyl 2-bromoacetate (3.34 g, 20 mmol) in CCl₄ (30 ml) was added. The mixture was stirred and refluxed for 8 h. After cooling, precipitates were filtered, washed by water and ethanol, and dried in vacuum. Single crystals suitable for X-ray diffraction were grown from methanol solution by slow evaporation in air at room temperature.