Methyl 7-chloro-2-ethyl­sulfanyl-6-fluoro-4-oxo-4H-thio­chromene-3-carboxyl­ate

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

doi:10.1107/S1600536810002667

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o694

doi:10.1107/S1600536810002667

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Methyl 7-chloro-2-ethylsulfanyl-6-fluoro-4-oxo-4H-thiochromene-3-carboxylate

Yang Li,^a Tao Xiao,^a ^* Dong-liang Liu ^a and Guang-yan Yu ^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 16 January 2010; accepted 21 January 2010; online 27 February 2010)

In the title compound, C₁₃H₁₀ClFO₃S₂, the two-ring system is essentially planar, the mean plane of the benzene ring being inclined at 6.0 (2)° to the plane of the remaining four atoms. The ethylsulfanyl group is almost coplanar with the two rings [dihedral angle = 6.4 (2)°], while the carboxylate group is almost perpendicular to it [dihedral angle = 72.4 (2)°]. In the crystal structure, intermolecular C—H⋯O and C—H⋯F 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 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₀ClFO₃S₂
M_r = 332.78
Triclinic, $[P \overline 1]$
a = 7.6740 (15) Å
b = 9.3880 (19) Å
c = 10.368 (2) Å
α = 85.18 (3)°
β = 80.93 (3)°
γ = 71.24 (3)°
V = 698.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.59 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 = 0.892, T_max = 0.944
2735 measured reflections
2531 independent reflections
1908 reflections with I > 2σ(I)
R_int = 0.016
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.138
S = 1.00
2531 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1ⁱ	0.93	2.60	3.292 (4)	132
C13—H13C⋯Fⁱⁱ	0.96	2.52	3.144 (5)	123
Symmetry codes: (i) x+1, y, z; (ii) -x-1, -y+1, -z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); 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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002667/zq2029sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810002667/zq2029Isup2.hkl

checkCIF report

Comment top

The title compound, methyl 7-chloro-2-(ethylsulfanyl)-6-fluoro-4-oxo-4H- thiochromene-3-carboxylate (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 molecule is essentially planar, the atoms C7, C8, C9 and S1 form a plane inclined at 6.0 (2)° with the mean plane of the phenyl ring. The ethylsulfanyl group is almost coplanar with the two rings while the carboxylate group is almost perpendicular. In the crystal structure, intermolecular C—H···O and C—H···F hydrogen bonds (Table 2) link the molecules in a stacked arrangement along the a axis (Fig. 2).

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). For bond-length data, see: Allen et al. (1987).

Experimental top

CS₂ (1.0 g, 13.1 mmol) was dropwise added to a solution of methyl 3-(4-chloro-3-fluorophenyl)-3-oxopropanoate (4 g, 17.3 mmol) in DMSO (20 ml) containing KOH (1 g, 17.8 mmol). The yellow solution was stirred for about 2 h at room temperature. Then bromoethane (1.9 g, 17.3 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 (I) in acetone (20 ml) and slow evaporation of the solvent at room temperature for about 7 d.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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 (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Methyl 7-chloro-2-ethylsulfanyl-6-fluoro-4-oxo-4H-thiochromene-3-carboxylate top

Crystal data top

C₁₃H₁₀ClFO₃S₂	Z = 2
M_r = 332.78	F(000) = 340
Triclinic, P1	D_x = 1.583 Mg m⁻³
Hall symbol: -P 1	Melting point: 421 K
a = 7.6740 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3880 (19) Å	Cell parameters from 25 reflections
c = 10.368 (2) Å	θ = 10–13°
α = 85.18 (3)°	µ = 0.59 mm⁻¹
β = 80.93 (3)°	T = 293 K
γ = 71.24 (3)°	Block, colourless
V = 698.0 (2) Å³	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1908 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 25.3°, θ_min = 2.0°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −10→11
T_min = 0.892, T_max = 0.944	l = −12→12
2735 measured reflections	3 standard reflections every 200 reflections
2531 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.085P)²] where P = (F_o² + 2F_c²)/3
2531 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₃H₁₀ClFO₃S₂	γ = 71.24 (3)°
M_r = 332.78	V = 698.0 (2) Å³
Triclinic, P1	Z = 2
a = 7.6740 (15) Å	Mo Kα radiation
b = 9.3880 (19) Å	µ = 0.59 mm⁻¹
c = 10.368 (2) Å	T = 293 K
α = 85.18 (3)°	0.20 × 0.10 × 0.10 mm
β = 80.93 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1908 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.016
T_min = 0.892, T_max = 0.944	3 standard reflections every 200 reflections
2735 measured reflections	intensity decay: 1%
2531 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.00	Δρ_max = 0.32 e Å⁻³
2531 reflections	Δρ_min = −0.31 e Å⁻³
181 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
Cl	0.32919 (13)	0.43804 (11)	−0.25035 (9)	0.0614 (3)
F	−0.0661 (3)	0.5608 (2)	−0.2592 (2)	0.0679 (6)
S1	0.13971 (10)	0.07054 (9)	0.12622 (8)	0.0409 (3)
S2	−0.04493 (12)	−0.08554 (10)	0.33572 (9)	0.0515 (3)
O1	−0.4369 (3)	0.3010 (3)	0.0513 (2)	0.0541 (6)
O2	−0.4884 (3)	0.2281 (3)	0.3453 (2)	0.0572 (7)
O3	−0.4571 (4)	0.0067 (3)	0.2676 (3)	0.0738 (8)
C1	0.0642 (4)	0.2176 (3)	0.0132 (3)	0.0353 (7)
C2	0.2053 (4)	0.2628 (3)	−0.0640 (3)	0.0403 (7)
H2A	0.3289	0.2153	−0.0531	0.048*
C3	0.1606 (4)	0.3769 (3)	−0.1554 (3)	0.0409 (7)
C4	−0.0260 (5)	0.4468 (4)	−0.1690 (3)	0.0460 (8)
C5	−0.1641 (4)	0.4052 (3)	−0.0954 (3)	0.0433 (8)
H5A	−0.2871	0.4546	−0.1070	0.052*
C6	−0.1220 (4)	0.2881 (3)	−0.0019 (3)	0.0357 (7)
C7	−0.2770 (4)	0.2453 (3)	0.0767 (3)	0.0394 (7)
C8	−0.2374 (4)	0.1375 (3)	0.1842 (3)	0.0364 (7)
C9	−0.0653 (4)	0.0524 (3)	0.2103 (3)	0.0359 (7)
C10	0.1994 (4)	−0.1669 (4)	0.3475 (3)	0.0478 (8)
H10A	0.2680	−0.2038	0.2638	0.057*
H10B	0.2482	−0.0928	0.3750	0.057*
C11	0.2151 (5)	−0.2962 (4)	0.4489 (4)	0.0616 (10)
H11A	0.3432	−0.3439	0.4593	0.092*
H11B	0.1659	−0.3683	0.4203	0.092*
H11C	0.1459	−0.2578	0.5310	0.092*
C12	−0.4059 (4)	0.1142 (4)	0.2676 (3)	0.0435 (8)
C13	−0.6523 (5)	0.2191 (5)	0.4322 (4)	0.0650 (11)
H13A	−0.7010	0.3066	0.4843	0.097*
H13B	−0.6200	0.1305	0.4882	0.097*
H13C	−0.7445	0.2141	0.3815	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0607 (6)	0.0691 (6)	0.0557 (6)	−0.0309 (5)	0.0054 (4)	0.0070 (4)
F	0.0703 (15)	0.0607 (13)	0.0659 (13)	−0.0157 (11)	−0.0153 (11)	0.0271 (11)
S1	0.0278 (4)	0.0440 (5)	0.0476 (5)	−0.0082 (3)	−0.0062 (3)	0.0060 (3)
S2	0.0359 (5)	0.0571 (6)	0.0557 (5)	−0.0118 (4)	−0.0047 (4)	0.0164 (4)
O1	0.0323 (12)	0.0591 (15)	0.0699 (16)	−0.0121 (11)	−0.0163 (11)	0.0109 (12)
O2	0.0491 (14)	0.0657 (16)	0.0583 (15)	−0.0270 (12)	0.0139 (12)	−0.0153 (12)
O3	0.0476 (15)	0.0571 (16)	0.119 (2)	−0.0274 (13)	0.0101 (15)	−0.0153 (16)
C1	0.0362 (16)	0.0339 (16)	0.0375 (16)	−0.0114 (13)	−0.0077 (13)	−0.0044 (13)
C2	0.0356 (16)	0.0406 (17)	0.0454 (18)	−0.0115 (14)	−0.0061 (14)	−0.0058 (14)
C3	0.0462 (18)	0.0416 (17)	0.0374 (16)	−0.0179 (15)	−0.0024 (14)	−0.0040 (14)
C4	0.057 (2)	0.0418 (18)	0.0398 (18)	−0.0144 (16)	−0.0116 (16)	0.0019 (14)
C5	0.0384 (17)	0.0396 (18)	0.0499 (19)	−0.0059 (14)	−0.0125 (15)	−0.0032 (15)
C6	0.0349 (16)	0.0340 (15)	0.0384 (16)	−0.0088 (13)	−0.0075 (13)	−0.0052 (12)
C7	0.0306 (16)	0.0392 (17)	0.0467 (18)	−0.0071 (13)	−0.0068 (14)	−0.0048 (14)
C8	0.0293 (15)	0.0395 (16)	0.0429 (17)	−0.0133 (13)	−0.0051 (13)	−0.0050 (13)
C9	0.0346 (16)	0.0373 (16)	0.0369 (16)	−0.0127 (13)	−0.0044 (13)	−0.0025 (13)
C10	0.0395 (18)	0.050 (2)	0.054 (2)	−0.0131 (15)	−0.0134 (15)	0.0088 (16)
C11	0.054 (2)	0.063 (2)	0.065 (2)	−0.0148 (19)	−0.0194 (19)	0.0168 (19)
C12	0.0283 (16)	0.0442 (18)	0.058 (2)	−0.0108 (14)	−0.0100 (14)	0.0046 (16)
C13	0.049 (2)	0.079 (3)	0.059 (2)	−0.019 (2)	0.0107 (18)	0.002 (2)

Geometric parameters (Å, º) top

Cl—C3	1.719 (3)	C5—C6	1.394 (4)
F—C4	1.352 (4)	C5—H5A	0.9300
S1—C9	1.726 (3)	C6—C7	1.480 (4)
S1—C1	1.744 (3)	C7—C8	1.441 (4)
S2—C9	1.744 (3)	C8—C9	1.362 (4)
S2—C10	1.802 (3)	C8—C12	1.505 (4)
O1—C7	1.231 (4)	C10—C11	1.524 (4)
O2—C12	1.320 (4)	C10—H10A	0.9700
O2—C13	1.448 (4)	C10—H10B	0.9700
O3—C12	1.195 (4)	C11—H11A	0.9600
C1—C6	1.396 (4)	C11—H11B	0.9600
C1—C2	1.400 (4)	C11—H11C	0.9600
C2—C3	1.363 (4)	C13—H13A	0.9600
C2—H2A	0.9300	C13—H13B	0.9600
C3—C4	1.394 (5)	C13—H13C	0.9600
C4—C5	1.349 (5)

C9—S1—C1	103.12 (15)	C7—C8—C12	114.8 (3)
C9—S2—C10	106.87 (15)	C8—C9—S1	124.2 (2)
C12—O2—C13	116.1 (3)	C8—C9—S2	119.3 (2)
C6—C1—C2	120.8 (3)	S1—C9—S2	116.45 (17)
C6—C1—S1	124.0 (2)	C11—C10—S2	105.9 (2)
C2—C1—S1	115.1 (2)	C11—C10—H10A	110.6
C3—C2—C1	119.7 (3)	S2—C10—H10A	110.6
C3—C2—H2A	120.2	C11—C10—H10B	110.6
C1—C2—H2A	120.2	S2—C10—H10B	110.6
C2—C3—C4	118.9 (3)	H10A—C10—H10B	108.7
C2—C3—Cl	121.1 (3)	C10—C11—H11A	109.5
C4—C3—Cl	119.9 (3)	C10—C11—H11B	109.5
C5—C4—F	120.0 (3)	H11A—C11—H11B	109.5
C5—C4—C3	122.4 (3)	C10—C11—H11C	109.5
F—C4—C3	117.5 (3)	H11A—C11—H11C	109.5
C4—C5—C6	119.8 (3)	H11B—C11—H11C	109.5
C4—C5—H5A	120.1	O3—C12—O2	123.8 (3)
C6—C5—H5A	120.1	O3—C12—C8	125.7 (3)
C5—C6—C1	118.4 (3)	O2—C12—C8	110.4 (3)
C5—C6—C7	118.3 (3)	O2—C13—H13A	109.5
C1—C6—C7	123.3 (3)	O2—C13—H13B	109.5
O1—C7—C8	120.6 (3)	H13A—C13—H13B	109.5
O1—C7—C6	120.7 (3)	O2—C13—H13C	109.5
C8—C7—C6	118.7 (3)	H13A—C13—H13C	109.5
C9—C8—C7	125.9 (3)	H13B—C13—H13C	109.5
C9—C8—C12	119.1 (3)

C9—S1—C1—C6	−3.7 (3)	C1—C6—C7—C8	7.3 (4)
C9—S1—C1—C2	176.1 (2)	O1—C7—C8—C9	169.8 (3)
C6—C1—C2—C3	−0.2 (4)	C6—C7—C8—C9	−10.5 (5)
S1—C1—C2—C3	180.0 (2)	O1—C7—C8—C12	−6.3 (4)
C1—C2—C3—C4	0.5 (4)	C6—C7—C8—C12	173.4 (3)
C1—C2—C3—Cl	178.9 (2)	C7—C8—C9—S1	6.0 (5)
C2—C3—C4—C5	−0.3 (5)	C12—C8—C9—S1	−178.0 (2)
Cl—C3—C4—C5	−178.8 (3)	C7—C8—C9—S2	−173.7 (2)
C2—C3—C4—F	179.2 (3)	C12—C8—C9—S2	2.3 (4)
Cl—C3—C4—F	0.7 (4)	C1—S1—C9—C8	1.0 (3)
F—C4—C5—C6	−179.6 (3)	C1—S1—C9—S2	−179.22 (16)
C3—C4—C5—C6	−0.2 (5)	C10—S2—C9—C8	−176.9 (2)
C4—C5—C6—C1	0.5 (5)	C10—S2—C9—S1	3.3 (2)
C4—C5—C6—C7	−179.8 (3)	C9—S2—C10—C11	−175.0 (2)
C2—C1—C6—C5	−0.3 (4)	C13—O2—C12—O3	−1.3 (5)
S1—C1—C6—C5	179.6 (2)	C13—O2—C12—C8	−179.4 (3)
C2—C1—C6—C7	180.0 (3)	C9—C8—C12—O3	−70.7 (5)
S1—C1—C6—C7	−0.1 (4)	C7—C8—C12—O3	105.7 (4)
C5—C6—C7—O1	7.3 (4)	C9—C8—C12—O2	107.4 (3)
C1—C6—C7—O1	−173.0 (3)	C7—C8—C12—O2	−76.2 (3)
C5—C6—C7—C8	−172.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.93	2.60	3.292 (4)	132
C13—H13C···Fⁱⁱ	0.96	2.52	3.144 (5)	123

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClFO₃S₂
M_r	332.78
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.6740 (15), 9.3880 (19), 10.368 (2)
α, β, γ (°)	85.18 (3), 80.93 (3), 71.24 (3)
V (Å³)	698.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
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	0.892, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	2735, 2531, 1908
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.138, 1.00
No. of reflections	2531
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.31

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cl—C3	1.719 (3)	S2—C10	1.802 (3)
F—C4	1.352 (4)	O1—C7	1.231 (4)
S1—C9	1.726 (3)	O2—C12	1.320 (4)
S1—C1	1.744 (3)	O2—C13	1.448 (4)
S2—C9	1.744 (3)	O3—C12	1.195 (4)

C9—S1—C1	103.12 (15)	O1—C7—C8	120.6 (3)
C9—S2—C10	106.87 (15)	O1—C7—C6	120.7 (3)
C12—O2—C13	116.1 (3)	C8—C9—S1	124.2 (2)
C6—C1—S1	124.0 (2)	C8—C9—S2	119.3 (2)
C2—C1—S1	115.1 (2)	S1—C9—S2	116.45 (17)
C2—C3—Cl	121.1 (3)	C11—C10—S2	105.9 (2)
C4—C3—Cl	119.9 (3)	O3—C12—O2	123.8 (3)
C5—C4—F	120.0 (3)	O3—C12—C8	125.7 (3)
F—C4—C3	117.5 (3)	O2—C12—C8	110.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.9300	2.6000	3.292 (4)	132.00
C13—H13C···Fⁱⁱ	0.9600	2.5200	3.144 (5)	123.00

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

Acknowledgements

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

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