Ethyl 2-{[7-fluoro-4-oxo-3-(1H-1,2,4-triazol-1-yl)-4H-thio­chromen-2-yl]sulfan­yl}acetate

Yang Li; Tao Xiao; Guang-yan Yu; Dong-liang Liu

doi:10.1107/S1600536810027467

. 2010 Jul 21;66(Pt 8):o2072. doi: 10.1107/S1600536810027467

Ethyl 2-{[7-fluoro-4-oxo-3-(1H-1,2,4-triazol-1-yl)-4H-thiochromen-2-yl]sulfanyl}acetate

Yang Li ^a, Tao Xiao ^a,^*, Guang-yan Yu ^a, Dong-liang Liu ^a

PMCID: PMC3007513 PMID: 21588373

Abstract

In the title compound, C₁₅H₁₂FN₃O₃S₂, the two six-membered rings are essentially coplanar, their mean plnes making a dihedral angle of 1.1 (2)°. The carbonyl C, the two attached non-fused C atoms and the S atom deviate from the plane of the benzene ring by −0.046 (5), −0.017 (5), 0.000 (6), 0.026 (4) Å, respectively. The angle between the mean planes of the triazole ring and the sulfur heterocycle is 53.3 (1)°. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules in a stacked arrangement along the a axis.

Related literature

For related compounds containing a 4H-thiochromen-4-one fragment, see: Adams et al. (1991 ▶); Nakazumi et al. (1992 ▶); Weiss et al. (2008 ▶); Li et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₂FN₃O₃S₂
M _r = 365.40
Monoclinic,
a = 9.3890 (19) Å
b = 8.2430 (16) Å
c = 20.861 (4) Å
β = 100.72 (3)°
V = 1586.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.898, T _max = 0.964
3053 measured reflections
2867 independent reflections
2186 reflections with I > 2σ(I)
R _int = 0.013
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.151
S = 1.00
2867 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810027467/zq2047sup1.cif

e-66-o2072-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027467/zq2047Isup2.hkl

e-66-o2072-Isup2.hkl^{(140.7KB, 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
C4—H4A⋯O2ⁱ	0.97	2.47	3.199 (4)	131
C11—H11A⋯O2ⁱⁱ	0.93	2.43	3.276 (4)	151

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound, ethyl 2-((7-fluoro-4-oxo-3-(1H-1,2,4-triazol-1-yl)-4H-thiochromen-2-yl)thio) acetate (I), is a new molecule which has a potential use as antifungal. We herein report its crystal structure.

The molecular structure of (I) is shown in Fig. 1, and selected geometric parameters are given in Table 1. The bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). The two-ring system is essentially planar [angle between the mean planes = 1.1 (2)°]. The atoms C7, C8, C15 and S2 deviate from the benzene ring by -0.046 (5), -0.017 (5), 0.000 (6), 0.026 (4) Å, respectively. The angle between the mean planes of the triazole ring and the sulfur heterocycle is 53.3 (1)°.

In the crystal packing, a weak intramolecular C4—H4B···S2 interaction is observed, and intermolecular C—H···O hydrogen bonds link the molecules in a stacked arrangement along the a axis.

Experimental

CS₂ (2.0 g, 26.3 mmol) was dropwise added to a solution of 1-(2,4- difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (5 g, 22.4 mmol) in DMSO (20 ml) containing NaOH (1.8 g, 45 mmol). The yellow solution was stirred for about 2 h at room temperature. Then ethyl bromoacetate (3.8 g, 22.4 mmol) was dropwise added to the intermediate. After 3 h, the solution was poured into water (50 ml). The crystalline product was isolated by filtration, and washed with water (300 ml). The crystals were obtained by dissolving (I) in acetone (20 ml) and evaporating acetone slowly at room temperature for about 7 d.