7-Fluoro-2-(prop-2-en-1-ylsulfan­yl)-3-(1H-1,2,4-triazol-1-yl)-4H-thio­chromen-4-one

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

doi:10.1107/S1600536811022665

. 2011 Jun 22;67(Pt 7):o1777. doi: 10.1107/S1600536811022665

7-Fluoro-2-(prop-2-en-1-ylsulfanyl)-3-(1H-1,2,4-triazol-1-yl)-4H-thiochromen-4-one

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

PMCID: PMC3151981 PMID: 21837153

Abstract

The asymmetric unit of the title compound, C₁₄H₁₀FN₃OS₂, contains two independent molecules which differ in the relative orientations of the triazole and allylsulfanyl groups with respect to the planar thiochromen-4-one frameworks. The N—N—C—C torsion angles are 128.2 (5) and −120.9 (5)°, while the C—S—C—S torsion angles are −17.4 (4) and 16.4 (4)°. In the crystal, intermolecular C—H⋯O and C—H⋯N 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. (2010a ▶,b ▶); Xiao et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₀FN₃OS₂
M _r = 319.39
Triclinic,
a = 8.1730 (16) Å
b = 11.646 (2) Å
c = 15.124 (3) Å
α = 82.43 (3)°
β = 83.98 (3)°
γ = 80.14 (3)°
V = 1400.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.926, T _max = 0.962
5541 measured reflections
5149 independent reflections
3087 reflections with I > 2σ(I)
R _int = 0.037
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.176
S = 1.01
5149 reflections
379 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985) ▶; cell refinement: CAD-4 Software ▶; 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 datablock(s) I, global. DOI: 10.1107/S1600536811022665/zq2103sup1.cif

e-67-o1777-sup1.cif^{(25KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022665/zq2103Isup2.hkl

e-67-o1777-Isup2.hkl^{(252.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811022665/zq2103Isup3.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
C1—H1A⋯O2ⁱ	0.93	2.50	3.328 (5)	149
C4—H4A⋯N5ⁱⁱ	0.93	2.61	3.397 (7)	143
C15—H15A⋯O1	0.93	2.56	3.372 (6)	147
C18—H18A⋯N2ⁱⁱⁱ	0.93	2.48	3.355 (7)	157

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

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound, C₁₄H₁₀FN₃OS₂, is a new molecule which has a potential use as antifungal. We herein report its crystal structure. The bond lengths and angles are within normal ranges (Allen et al., 1987). The asymmetric unit contains two independent molecules. They differ in the relative orientations of the triazole and allylsulfanyl groups with respect to the planar thiochromen-4-one frameworks. The dihedral angles N3—N1—C8—C7 and the corresponding N6—N4—C22—C21 are 128.2 (5)° and -120.9 (5)° while the dihedral angles C26—S4—C23—S3 and C12—S2—C9—S1 are -17.4 (4)° and 16.4 (4)°. The two-ring system is essentially planar in each molecule. The dihedral angles between the mean planes of the benzene rings and of the C₅S rings are 2.7 (2) and 2.9 (2)°. In the crystal structure, intermolecular C—H···O and C—H···N 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 allyl chloride (1.7 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, washed with water (300 ml). The crystals were obtained by dissolving the title compound in acetone (20 ml) and evaporating acetone slowly at room temperature for about 7 d.