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

Liu, D.; Xiao, T.; Li, Y.; Yu, G.; Li, C.

doi:10.1107/S1600536811022665

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1777

doi:10.1107/S1600536811022665

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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 and Chen Li ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: taoxiao@njut.edu.cn

(Received 10 May 2011; accepted 11 June 2011; online 22 June 2011)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.069
wR(F²) = 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

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
Symmetry codes: (i) x, y, z-1; (ii) -x, -y+1, -z+2; (iii) -x+1, -y+1, -z+2.

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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811022665/zq2103sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811022665/zq2103Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound.

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

Crystal data top

C₁₄H₁₀FN₃OS₂	Z = 4
M_r = 319.39	F(000) = 656
Triclinic, P1	D_x = 1.514 Mg m⁻³
Hall symbol: -P 1	Melting point: 385 K
a = 8.1730 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.646 (2) Å	Cell parameters from 25 reflections
c = 15.124 (3) Å	θ = 9–12°
α = 82.43 (3)°	µ = 0.39 mm⁻¹
β = 83.98 (3)°	T = 293 K
γ = 80.14 (3)°	Block, yellow
V = 1400.9 (5) Å³	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	3087 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 25.5°, θ_min = 1.4°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −13→14
T_min = 0.926, T_max = 0.962	l = −18→18
5541 measured reflections	3 standard reflections every 200 reflections
5149 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.080P)² + 1.P] where P = (F_o² + 2F_c²)/3
5149 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.52 e Å⁻³
1 restraint	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₄H₁₀FN₃OS₂	γ = 80.14 (3)°
M_r = 319.39	V = 1400.9 (5) Å³
Triclinic, P1	Z = 4
a = 8.1730 (16) Å	Mo Kα radiation
b = 11.646 (2) Å	µ = 0.39 mm⁻¹
c = 15.124 (3) Å	T = 293 K
α = 82.43 (3)°	0.20 × 0.10 × 0.10 mm
β = 83.98 (3)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.069	1 restraint
wR(F²) = 0.176	H-atom parameters constrained
S = 1.01	Δρ_max = 0.52 e Å⁻³
5149 reflections	Δρ_min = −0.40 e Å⁻³
379 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.44048 (18)	0.30108 (12)	0.42901 (7)	0.0563 (4)
O1	0.3291 (5)	0.4374 (3)	0.69021 (19)	0.0718 (11)
F1	0.0540 (4)	0.6601 (3)	0.3288 (2)	0.0787 (10)
N1	0.5146 (5)	0.2210 (3)	0.6888 (2)	0.0472 (10)
C1	0.2380 (6)	0.4976 (4)	0.3820 (3)	0.0511 (12)
H1A	0.2597	0.4748	0.3247	0.061*
S2	0.64594 (19)	0.10674 (12)	0.52776 (8)	0.0604 (4)
N2	0.6087 (6)	0.1689 (4)	0.8194 (3)	0.0640 (12)
C2	0.1322 (7)	0.5970 (5)	0.3969 (3)	0.0538 (13)
C3	0.1006 (6)	0.6363 (4)	0.4802 (3)	0.0552 (13)
H3A	0.0285	0.7057	0.4886	0.066*
N3	0.4931 (6)	0.1073 (4)	0.7111 (2)	0.0610 (12)
C4	0.1774 (6)	0.5709 (4)	0.5491 (3)	0.0526 (13)
H4A	0.1579	0.5967	0.6054	0.063*
C5	0.2847 (6)	0.4662 (4)	0.5386 (3)	0.0414 (11)
C6	0.3135 (6)	0.4303 (4)	0.4532 (3)	0.0419 (11)
C7	0.3553 (6)	0.3979 (4)	0.6171 (3)	0.0495 (12)
C8	0.4592 (6)	0.2856 (4)	0.6084 (3)	0.0428 (11)
C9	0.5093 (6)	0.2390 (4)	0.5298 (3)	0.0457 (11)
C10	0.5830 (7)	0.2549 (5)	0.7553 (3)	0.0563 (14)
H10A	0.6088	0.3295	0.7559	0.068*
C11	0.5504 (8)	0.0820 (5)	0.7890 (3)	0.0659 (16)
H11A	0.5510	0.0085	0.8218	0.079*
C12	0.7155 (8)	0.1027 (5)	0.4101 (3)	0.0734 (18)
H12A	0.6357	0.0727	0.3799	0.088*
H12B	0.7267	0.1810	0.3817	0.088*
C13	0.8773 (11)	0.0255 (7)	0.4051 (4)	0.108 (3)
H13A	0.9647	0.0519	0.4269	0.129*
C14	0.9121 (11)	−0.0722 (6)	0.3748 (4)	0.112 (3)
H14A	0.8299	−0.1031	0.3520	0.134*
H14B	1.0201	−0.1134	0.3751	0.134*
S3	0.24689 (18)	0.41381 (11)	0.89646 (7)	0.0544 (4)
S4	0.1326 (2)	0.20977 (13)	1.00091 (8)	0.0656 (4)
F2	0.4001 (4)	0.8034 (3)	0.78292 (18)	0.0770 (10)
N4	0.1606 (5)	0.3240 (3)	1.1599 (2)	0.0478 (10)
N5	0.0575 (6)	0.2723 (4)	1.2953 (3)	0.0605 (12)
N6	0.2392 (6)	0.2129 (4)	1.1815 (3)	0.0635 (13)
O2	0.2657 (5)	0.5303 (3)	1.15925 (19)	0.0618 (10)
C15	0.3312 (6)	0.6232 (4)	0.8431 (3)	0.0516 (13)
H15A	0.3294	0.6027	0.7859	0.062*
C16	0.3687 (7)	0.7272 (5)	0.8545 (3)	0.0553 (13)
C17	0.3756 (7)	0.7615 (5)	0.9382 (3)	0.0568 (13)
H17A	0.4038	0.8339	0.9444	0.068*
C18	0.3395 (6)	0.6851 (4)	1.0112 (3)	0.0518 (13)
H18A	0.3440	0.7063	1.0680	0.062*
C19	0.2964 (6)	0.5765 (4)	1.0038 (3)	0.0417 (11)
C20	0.2946 (6)	0.5460 (4)	0.9182 (3)	0.0431 (11)
C21	0.2567 (6)	0.4993 (4)	1.0857 (3)	0.0428 (11)
C22	0.2014 (6)	0.3908 (4)	1.0784 (3)	0.0416 (11)
C23	0.1920 (6)	0.3458 (4)	1.0007 (3)	0.0463 (12)
C24	0.0550 (6)	0.3569 (5)	1.2292 (3)	0.0528 (13)
H24A	−0.0114	0.4301	1.2301	0.063*
C25	0.1744 (8)	0.1885 (5)	1.2630 (3)	0.0685 (16)
H25A	0.2072	0.1171	1.2969	0.082*
C26	0.0874 (8)	0.2065 (5)	0.8870 (3)	0.0665 (16)
H26A	0.0070	0.2745	0.8682	0.080*
H26B	0.1882	0.2071	0.8470	0.080*
C27	0.0185 (10)	0.0971 (6)	0.8850 (4)	0.094 (2)
H27A	−0.0860	0.0931	0.9150	0.113*
C28	0.0857 (11)	0.0102 (6)	0.8476 (4)	0.105 (3)
H28C	0.1904	0.0097	0.8166	0.126*
H28A	0.0315	−0.0543	0.8504	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0737 (10)	0.0671 (9)	0.0274 (6)	0.0032 (7)	−0.0070 (5)	−0.0204 (5)
O1	0.108 (3)	0.080 (3)	0.0250 (16)	0.005 (2)	−0.0030 (17)	−0.0291 (16)
F1	0.091 (3)	0.081 (2)	0.0559 (18)	0.0140 (19)	−0.0192 (17)	−0.0051 (16)
N1	0.067 (3)	0.052 (2)	0.0259 (18)	−0.015 (2)	−0.0017 (17)	−0.0117 (16)
C1	0.056 (3)	0.068 (3)	0.033 (2)	−0.012 (3)	−0.004 (2)	−0.014 (2)
S2	0.0812 (10)	0.0641 (9)	0.0325 (6)	0.0045 (7)	−0.0051 (6)	−0.0139 (6)
N2	0.086 (4)	0.068 (3)	0.040 (2)	−0.010 (3)	−0.017 (2)	−0.007 (2)
C2	0.060 (3)	0.059 (3)	0.042 (3)	−0.009 (3)	−0.007 (2)	−0.003 (2)
C3	0.054 (3)	0.055 (3)	0.054 (3)	−0.002 (3)	0.001 (2)	−0.013 (2)
N3	0.095 (4)	0.059 (3)	0.034 (2)	−0.022 (2)	−0.005 (2)	−0.0076 (18)
C4	0.060 (3)	0.063 (3)	0.035 (2)	−0.009 (3)	0.005 (2)	−0.015 (2)
C5	0.043 (3)	0.054 (3)	0.030 (2)	−0.012 (2)	0.0027 (19)	−0.0129 (19)
C6	0.047 (3)	0.054 (3)	0.028 (2)	−0.012 (2)	−0.0005 (19)	−0.0150 (19)
C7	0.056 (3)	0.068 (3)	0.029 (2)	−0.017 (3)	0.003 (2)	−0.018 (2)
C8	0.055 (3)	0.052 (3)	0.025 (2)	−0.017 (2)	−0.0035 (19)	−0.0091 (19)
C9	0.051 (3)	0.058 (3)	0.033 (2)	−0.016 (2)	−0.002 (2)	−0.014 (2)
C10	0.079 (4)	0.056 (3)	0.038 (3)	−0.011 (3)	−0.014 (2)	−0.016 (2)
C11	0.099 (5)	0.066 (4)	0.034 (3)	−0.019 (3)	−0.003 (3)	−0.006 (2)
C12	0.089 (4)	0.084 (4)	0.034 (3)	0.028 (3)	−0.001 (3)	−0.018 (3)
C13	0.143 (7)	0.116 (6)	0.047 (4)	0.031 (5)	−0.007 (4)	−0.013 (4)
C14	0.152 (8)	0.096 (6)	0.077 (5)	0.025 (5)	−0.022 (5)	−0.018 (4)
S3	0.0840 (10)	0.0579 (8)	0.0237 (5)	−0.0125 (7)	−0.0015 (5)	−0.0138 (5)
S4	0.0998 (12)	0.0617 (9)	0.0420 (7)	−0.0247 (8)	−0.0080 (7)	−0.0136 (6)
F2	0.113 (3)	0.081 (2)	0.0412 (16)	−0.039 (2)	−0.0052 (16)	0.0077 (15)
N4	0.062 (3)	0.057 (3)	0.0225 (18)	−0.005 (2)	−0.0003 (17)	−0.0076 (16)
N5	0.076 (3)	0.064 (3)	0.039 (2)	−0.014 (2)	0.013 (2)	−0.008 (2)
N6	0.089 (4)	0.056 (3)	0.036 (2)	0.001 (2)	0.010 (2)	−0.0021 (18)
O2	0.098 (3)	0.071 (2)	0.0242 (16)	−0.025 (2)	−0.0040 (16)	−0.0166 (15)
C15	0.065 (3)	0.061 (3)	0.031 (2)	−0.013 (3)	−0.006 (2)	−0.006 (2)
C16	0.064 (4)	0.065 (3)	0.036 (3)	−0.016 (3)	0.000 (2)	0.001 (2)
C17	0.075 (4)	0.059 (3)	0.041 (3)	−0.020 (3)	−0.005 (2)	−0.008 (2)
C18	0.065 (3)	0.060 (3)	0.033 (2)	−0.011 (3)	−0.008 (2)	−0.011 (2)
C19	0.045 (3)	0.051 (3)	0.028 (2)	0.000 (2)	−0.0042 (18)	−0.0087 (19)
C20	0.044 (3)	0.052 (3)	0.033 (2)	−0.004 (2)	−0.0044 (19)	−0.0087 (19)
C21	0.047 (3)	0.056 (3)	0.025 (2)	−0.004 (2)	−0.0011 (18)	−0.0099 (19)
C22	0.046 (3)	0.049 (3)	0.029 (2)	−0.005 (2)	−0.0012 (19)	−0.0078 (19)
C23	0.056 (3)	0.052 (3)	0.030 (2)	−0.002 (2)	−0.002 (2)	−0.012 (2)
C24	0.062 (3)	0.061 (3)	0.037 (3)	−0.013 (3)	0.008 (2)	−0.015 (2)
C25	0.098 (5)	0.064 (4)	0.036 (3)	−0.004 (3)	0.004 (3)	0.002 (2)
C26	0.098 (5)	0.057 (3)	0.048 (3)	−0.011 (3)	−0.011 (3)	−0.018 (2)
C27	0.131 (6)	0.103 (6)	0.060 (4)	−0.042 (5)	−0.009 (4)	−0.028 (4)
C28	0.166 (8)	0.092 (5)	0.066 (4)	−0.037 (5)	0.001 (4)	−0.032 (4)

Geometric parameters (Å, º) top

S1—C9	1.706 (5)	S3—C23	1.720 (4)
S1—C6	1.734 (5)	S3—C20	1.731 (5)
O1—C7	1.237 (5)	S4—C23	1.734 (5)
F1—C2	1.337 (5)	S4—C26	1.806 (5)
N1—C10	1.334 (5)	F2—C16	1.339 (5)
N1—N3	1.359 (5)	N4—C24	1.339 (5)
N1—C8	1.416 (5)	N4—N6	1.357 (5)
C1—C2	1.350 (7)	N4—C22	1.409 (5)
C1—C6	1.380 (6)	N5—C24	1.307 (6)
C1—H1A	0.9300	N5—C25	1.347 (6)
S2—C9	1.743 (5)	N6—C25	1.305 (6)
S2—C12	1.814 (5)	O2—C21	1.227 (5)
N2—C10	1.305 (6)	C15—C16	1.335 (7)
N2—C11	1.340 (7)	C15—C20	1.393 (6)
C2—C3	1.381 (6)	C15—H15A	0.9300
C3—C4	1.350 (7)	C16—C17	1.387 (6)
C3—H3A	0.9300	C17—C18	1.364 (6)
N3—C11	1.293 (6)	C17—H17A	0.9300
C4—C5	1.392 (6)	C18—C19	1.391 (6)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.393 (5)	C19—C20	1.389 (6)
C5—C7	1.454 (6)	C19—C21	1.473 (6)
C7—C8	1.446 (7)	C21—C22	1.435 (6)
C8—C9	1.367 (6)	C22—C23	1.362 (6)
C10—H10A	0.9300	C24—H24A	0.9300
C11—H11A	0.9300	C25—H25A	0.9300
C12—C13	1.467 (9)	C26—C27	1.484 (8)
C12—H12A	0.9700	C26—H26A	0.9700
C12—H12B	0.9700	C26—H26B	0.9700
C13—C14	1.259 (7)	C27—C28	1.241 (9)
C13—H13A	0.9300	C27—H27A	0.9300
C14—H14A	0.9300	C28—H28C	0.9300
C14—H14B	0.9300	C28—H28A	0.9300

C9—S1—C6	104.0 (2)	C23—S3—C20	103.9 (2)
C10—N1—N3	108.5 (4)	C23—S4—C26	104.5 (2)
C10—N1—C8	130.2 (4)	C24—N4—N6	109.1 (4)
N3—N1—C8	121.2 (4)	C24—N4—C22	128.8 (4)
C2—C1—C6	118.9 (4)	N6—N4—C22	121.9 (4)
C2—C1—H1A	120.5	C24—N5—C25	101.9 (4)
C6—C1—H1A	120.5	C25—N6—N4	101.7 (4)
C9—S2—C12	103.8 (2)	C16—C15—C20	119.0 (4)
C10—N2—C11	102.7 (4)	C16—C15—H15A	120.5
F1—C2—C1	119.2 (4)	C20—C15—H15A	120.5
F1—C2—C3	118.3 (5)	C15—C16—F2	119.7 (4)
C1—C2—C3	122.5 (5)	C15—C16—C17	122.9 (5)
C4—C3—C2	118.0 (5)	F2—C16—C17	117.5 (5)
C4—C3—H3A	121.0	C18—C17—C16	117.5 (5)
C2—C3—H3A	121.0	C18—C17—H17A	121.2
C11—N3—N1	102.7 (4)	C16—C17—H17A	121.2
C3—C4—C5	122.2 (4)	C17—C18—C19	122.4 (4)
C3—C4—H4A	118.9	C17—C18—H18A	118.8
C5—C4—H4A	118.9	C19—C18—H18A	118.8
C4—C5—C6	117.8 (4)	C20—C19—C18	117.6 (4)
C4—C5—C7	118.7 (4)	C20—C19—C21	123.2 (4)
C6—C5—C7	123.5 (4)	C18—C19—C21	119.3 (4)
C1—C6—C5	120.5 (4)	C19—C20—C15	120.7 (4)
C1—C6—S1	115.9 (3)	C19—C20—S3	123.8 (4)
C5—C6—S1	123.6 (4)	C15—C20—S3	115.5 (3)
O1—C7—C8	120.6 (4)	O2—C21—C22	120.8 (4)
O1—C7—C5	119.9 (5)	O2—C21—C19	119.8 (4)
C8—C7—C5	119.5 (4)	C22—C21—C19	119.4 (4)
C9—C8—N1	118.4 (4)	C23—C22—N4	118.3 (4)
C9—C8—C7	125.4 (4)	C23—C22—C21	125.8 (4)
N1—C8—C7	116.2 (4)	N4—C22—C21	115.8 (4)
C8—C9—S1	123.7 (4)	C22—C23—S3	123.6 (4)
C8—C9—S2	120.8 (4)	C22—C23—S4	121.4 (4)
S1—C9—S2	115.5 (2)	S3—C23—S4	114.9 (2)
N2—C10—N1	110.6 (5)	N5—C24—N4	111.0 (5)
N2—C10—H10A	124.7	N5—C24—H24A	124.5
N1—C10—H10A	124.7	N4—C24—H24A	124.5
N3—C11—N2	115.5 (5)	N6—C25—N5	116.2 (5)
N3—C11—H11A	122.3	N6—C25—H25A	121.9
N2—C11—H11A	122.3	N5—C25—H25A	121.9
C13—C12—S2	107.3 (4)	C27—C26—S4	107.0 (4)
C13—C12—H12A	110.3	C27—C26—H26A	110.3
S2—C12—H12A	110.3	S4—C26—H26A	110.3
C13—C12—H12B	110.3	C27—C26—H26B	110.3
S2—C12—H12B	110.3	S4—C26—H26B	110.3
H12A—C12—H12B	108.5	H26A—C26—H26B	108.6
C14—C13—C12	127.8 (9)	C28—C27—C26	126.9 (8)
C14—C13—H13A	116.1	C28—C27—H27A	116.6
C12—C13—H13A	116.1	C26—C27—H27A	116.6
C13—C14—H14A	120.0	C27—C28—H28C	120.0
C13—C14—H14B	120.0	C27—C28—H28A	120.0
H14A—C14—H14B	120.0	H28C—C28—H28A	120.0

C6—C1—C2—F1	−177.5 (4)	C24—N4—N6—C25	−0.5 (6)
C6—C1—C2—C3	2.2 (8)	C22—N4—N6—C25	175.2 (5)
F1—C2—C3—C4	178.7 (5)	C20—C15—C16—F2	−178.4 (4)
C1—C2—C3—C4	−1.0 (8)	C20—C15—C16—C17	1.0 (8)
C10—N1—N3—C11	−0.1 (6)	C15—C16—C17—C18	−1.0 (8)
C8—N1—N3—C11	−176.8 (5)	F2—C16—C17—C18	178.4 (5)
C2—C3—C4—C5	−0.5 (8)	C16—C17—C18—C19	−0.3 (8)
C3—C4—C5—C6	0.9 (7)	C17—C18—C19—C20	1.5 (7)
C3—C4—C5—C7	−176.7 (5)	C17—C18—C19—C21	−179.1 (5)
C2—C1—C6—C5	−1.9 (7)	C18—C19—C20—C15	−1.5 (7)
C2—C1—C6—S1	177.3 (4)	C21—C19—C20—C15	179.1 (4)
C4—C5—C6—C1	0.4 (7)	C18—C19—C20—S3	179.1 (4)
C7—C5—C6—C1	177.8 (4)	C21—C19—C20—S3	−0.3 (7)
C4—C5—C6—S1	−178.8 (4)	C16—C15—C20—C19	0.3 (7)
C7—C5—C6—S1	−1.3 (7)	C16—C15—C20—S3	179.8 (4)
C9—S1—C6—C1	−178.8 (4)	C23—S3—C20—C19	4.4 (5)
C9—S1—C6—C5	0.4 (5)	C23—S3—C20—C15	−175.1 (4)
C4—C5—C7—O1	−5.2 (7)	C20—C19—C21—O2	177.7 (4)
C6—C5—C7—O1	177.4 (5)	C18—C19—C21—O2	−1.7 (7)
C4—C5—C7—C8	176.4 (4)	C20—C19—C21—C22	−4.7 (7)
C6—C5—C7—C8	−1.0 (7)	C18—C19—C21—C22	175.9 (4)
C10—N1—C8—C9	131.2 (5)	C24—N4—C22—C23	−128.9 (5)
N3—N1—C8—C9	−52.9 (6)	N6—N4—C22—C23	56.5 (6)
C10—N1—C8—C7	−47.7 (7)	C24—N4—C22—C21	53.8 (7)
N3—N1—C8—C7	128.2 (5)	N6—N4—C22—C21	−120.9 (5)
O1—C7—C8—C9	−173.4 (5)	O2—C21—C22—C23	−177.6 (5)
C5—C7—C8—C9	5.1 (7)	C19—C21—C22—C23	4.9 (7)
O1—C7—C8—N1	5.5 (7)	O2—C21—C22—N4	−0.5 (7)
C5—C7—C8—N1	−176.1 (4)	C19—C21—C22—N4	−178.0 (4)
N1—C8—C9—S1	174.9 (3)	N4—C22—C23—S3	−176.9 (3)
C7—C8—C9—S1	−6.3 (7)	C21—C22—C23—S3	0.1 (7)
N1—C8—C9—S2	−3.1 (6)	N4—C22—C23—S4	−0.3 (6)
C7—C8—C9—S2	175.8 (4)	C21—C22—C23—S4	176.8 (4)
C6—S1—C9—C8	3.3 (5)	C20—S3—C23—C22	−4.3 (5)
C6—S1—C9—S2	−178.7 (3)	C20—S3—C23—S4	178.8 (3)
C12—S2—C9—C8	−165.5 (4)	C26—S4—C23—C22	165.7 (4)
C12—S2—C9—S1	16.4 (4)	C26—S4—C23—S3	−17.4 (4)
C11—N2—C10—N1	−0.9 (6)	C25—N5—C24—N4	2.0 (6)
N3—N1—C10—N2	0.6 (6)	N6—N4—C24—N5	−1.1 (6)
C8—N1—C10—N2	176.9 (5)	C22—N4—C24—N5	−176.3 (4)
N1—N3—C11—N2	−0.5 (7)	N4—N6—C25—N5	1.9 (7)
C10—N2—C11—N3	0.9 (7)	C24—N5—C25—N6	−2.5 (7)
C9—S2—C12—C13	156.2 (5)	C23—S4—C26—C27	−174.1 (5)
S2—C12—C13—C14	113.6 (7)	S4—C26—C27—C28	−111.7 (7)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z+2; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀FN₃OS₂
M_r	319.39
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.1730 (16), 11.646 (2), 15.124 (3)
α, β, γ (°)	82.43 (3), 83.98 (3), 80.14 (3)
V (Å³)	1400.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.926, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	5541, 5149, 3087
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.176, 1.01
No. of reflections	5149
No. of parameters	379
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.40

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z+2; (iii) −x+1, −y+1, −z+2.

Acknowledgements

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

References

Adams, H., Bailey, N. A., Giles, P. R. & Marson, C. M. (1991). Acta Cryst. C47, 1332–1334. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Li, Y., Xiao, T., Liu, D. & Yu, G. (2010a). Acta Cryst. E66, o694. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, Y., Xiao, T., Yu, G. & Liu, D. (2010b). Acta Cryst. E66, o2072. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nakazumi, H., Watanabe, S. & Kitao, T. (1992). J. Chem. Res. 212, 1616-1641. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Weiss, R., Bess, M., Huber, S. M. & Heinemann, F. W. (2008). J. Am. Chem. Soc. 130, 4610-4617. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Volume 67| Part 7| July 2011| Page o1777

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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