2-(4,6-Dimethyl­pyrimidin-2-ylsulfan­yl)-N-(4-methyl­pyridin-2-yl)acetamide

Dong Liang; Li-Xing Gao; Yan Gao; Jing Xu; Wei Wang

doi:10.1107/S1600536807064082

. 2007 Dec 6;64(Pt 1):o201. doi: 10.1107/S1600536807064082

2-(4,6-Dimethylpyrimidin-2-ylsulfanyl)-N-(4-methylpyridin-2-yl)acetamide

Dong Liang ^a, Li-Xing Gao ^a, Yan Gao ^a, Jing Xu ^a, Wei Wang ^a,^*

PMCID: PMC2915263 PMID: 21200766

Abstract

The non-H atoms of the title molecule, C₁₄H₁₆N₄OS, are coplanar, with an r.m.s. deviation of 0.039 Å. The dihedral angle between the two aromatic rings is 2.4 (2)°. An intramolecular C—H⋯O hydrogen bond is observed. The molecules exist as N—H⋯N hydrogen-bonded centrosymmetric dimers.

Related literature

For related literature, see: Koike et al. (1999 ▶).

Experimental

Crystal data

C₁₄H₁₆N₄OS
M _r = 288.37
Monoclinic,
a = 5.1924 (19) Å
b = 15.423 (5) Å
c = 18.121 (6) Å
β = 91.678 (6)°
V = 1450.5 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 (2) K
0.40 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.916, T _max = 0.957
8084 measured reflections
2970 independent reflections
1582 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.144
S = 0.98
2970 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064082/ci2528sup1.cif

e-64-0o201-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064082/ci2528Isup2.hkl

e-64-0o201-Isup2.hkl^{(145.8KB, 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
N3—H3A⋯N4ⁱ	0.86	2.31	3.171 (3)	174
C10—H10⋯O1	0.93	2.20	2.821 (4)	123

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Acetamide is an important class of medical intermediate. Many biologically active compounds are prepared by using acetamide (Koike et al., 1999). The title compound was prepared from the reaction of 2-thio-4,6-dimethylpyrimidine with 2-chloro-N-(5-methylpyridin-2-yl)acetamide. We report here the crystal structure of the title compound.

The non-hydrogen atoms of the title molecule are coplanar, with an r.m.s. deviation of 0.039 Å. The dihedral angle between the two heterocyclic rings is 2.4 (2)°. The O1—C8—N3 [124.3 (2)°] and N3—C8—C7 [113.9 (2)°] angles deviate significantly from the ideal value of 120°. Due to the p-π conjugation bwtween the S atom and the pyrimidine ring, the S1—C1 bond distance [1.756 (3) Å] is slightly shorter than the S1—C7 bond distance [1.794 (3) Å]. An intramolecular C—H···O hydrogen bond is observed. The molecules exist as N—H···O hydrogen-bonded centrosymmetric dimer (Table 1).

Experimental

The title compound was synthesized by the reaction of 2-thio-4,6-dimethylpyrimidine (2 mmol) with 2-chloro-N-(5-methylpyridin-2-yl)acetamide (2 mmol) in refluxing ethanol (40 ml). Single crystals suitable for X-ray analysis were grown by slow evaporation of a chloroform-acetone (1:5 v/v) solution.