Ethyl 6-(2-chloro­phen­yl)-4-methyl-1-(3-oxobut­yl)-2-thioxo-1,2,3,6-tetra­hydro­pyrimidine-5-carboxyl­ate

Qing-Peng He; Jian-Yong Wang; Ruo-Kun Feng

doi:10.1107/S160053680706730X

. 2008 Jan 4;64(Pt 2):o352. doi: 10.1107/S160053680706730X

Ethyl 6-(2-chlorophenyl)-4-methyl-1-(3-oxobutyl)-2-thioxo-1,2,3,6-tetrahydropyrimidine-5-carboxylate

Qing-Peng He ^a,^*, Jian-Yong Wang ^a, Ruo-Kun Feng ^a

PMCID: PMC2960298 PMID: 21201384

Abstract

In the title molecule, C₁₈H₂₁ClN₂O₃S, the pyrimidine ring exhibits a half-chair conformation. The ethyl group is disordered between two positions in a ratio 0.74:0.26. In the crystal structure, the molecules are linked into chains along the a axis by N—H⋯O hydrogen bonds.

Related literature

For the crystal structure of a related compound, see Jiang et al. (2007 ▶).

Experimental

Crystal data

C₁₈H₂₁ClN₂O₃S
M _r = 380.88
Triclinic,
a = 7.5227 (12) Å
b = 9.7163 (15) Å
c = 14.122 (2) Å
α = 72.617 (6)°
β = 87.300 (6)°
γ = 71.296 (6)°
V = 931.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 273 (2) K
0.14 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.954, T _max = 0.967
10470 measured reflections
3233 independent reflections
2743 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.166
S = 1.00
3233 reflections
242 parameters
63 restraints
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706730X/cv2372sup1.cif

e-64-0o352-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706730X/cv2372Isup2.hkl

e-64-0o352-Isup2.hkl^{(158.6KB, 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
N1—H1⋯O1ⁱ	0.86	2.16	2.984 (3)	160

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (No. X051040).

supplementary crystallographic information

Comment

Herewith we present the crystal strusture of the title compound, (I), which was synthesized through the reaction of 2-chlorobenzaldehyde and ethyl acetoacetate with urea derivative under solvent-free conditions.

In (I) (Fig. 1), bond lengths and angles are normal and comparable with those observed in reported compound (Jiang et al., 2007). The pyrimidine ring exhibits a half-chair conformation with the maximal deviation of 0.168 Å for C6 from mean plane.

In the crystal, the molecules related by translation along axis a are linked into chains by N—H···O hydrogen bonds (Table 1).

Experimental

2-Chlorobenzaldehyde (2 mmol), ethyl acetoacetate (2 mmol), urea derivatives (2.4 mmol) and H₃BO₃(0.4 mmol), in glacial acetic acid (10 ml) was heated at 373 K, while stirring for 1 h, then cooled to room temperature, and poured into ice water (50 ml), and recrystallized from EtOH, affording the title compound as a colourless crystalline solid. Elemental analysis: calculated for C₁₈H₂₁ClN₂O₃S: C 56.76, H 5.56, N 7.35%; found: C 56.68, H 5.45, N 7.44%.