5-Cyclo­pentyl-2-(4-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzofuran

Seo, P.J.; Choi, H.D.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811036087

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2591

https://doi.org/10.1107/S1600536811036087

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5-Cyclopentyl-2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran

Pil Ja Seo,^a Hong Dae Choi,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 10 August 2011; accepted 5 September 2011; online 14 September 2011)

In the title compound, C₂₀H₁₉FO₂S, the cyclopentyl ring adopts an envelope conformation. The 4-fluorophenyl ring makes a dihedral angle of 27.10 (7)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions. In the cyclopentyl ring, one C atom is disordered over two orientations with site-occupancy factors of 0.617 (7) and 0.383 (7).

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For structural studies of related 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2010 , 2011 ).

Experimental

Crystal data

C₂₀H₁₉FO₂S
M_r = 342.41
Orthorhombic, F d d 2
a = 20.0254 (13) Å
b = 33.197 (2) Å
c = 10.0233 (7) Å
V = 6663.3 (8) Å³
Z = 16
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.35 × 0.26 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.930, T_max = 0.961
16962 measured reflections
4136 independent reflections
3915 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.106
S = 1.06
4136 reflections
223 parameters
96 restraints
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 1949 Friedel pairs
Flack parameter: 0.15 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1/C2/C7/O/C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯O2ⁱ	0.98	2.29	3.262 (3)	169
C16—H16⋯Cgⁱ	0.95	2.53	3.365 (3)	146
Symmetry code: (i) $[x-{\script{1\over 4}}, -y+{\script{1\over 4}}, z-{\script{1\over 4}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036087/gk2398sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036087/gk2398Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036087/gk2398Isup3.cml

checkCIF report

Comment top

Many compounds containing a benzofuran ring system have attracted much interest owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran analogues (Choi et al., 2010, 2011), we report herein the crystal structure of the title compound.

The title compound crystallizes ins the non-centrosymmetric space group Fdd2. The crystal studied was an inversion twin with a 0.85 (7) : 0.15 (7) domain ratio.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.024 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring is in the envelope form. In the cyclopentyl ring, the C10 atom is disordered over two positions with site-occupancy factors, from refinement of 0.617 (7) (part A) and 0.383 (7) (part B). The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 27.10 (7)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a methyl H atom and the O atom of the sulfinyl group (Table 1; C20—H20B···O2ⁱ). The crystal packing (Fig. 2) is further stabilized by intermolecular C—H···π interactions between a 4-fluorophenyl H atom and the furan ring (Table 1; C16—H16···Cgⁱ, Cg is the centroid of the C1/C2/C7/O1/C8 furan ring).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclopentyl-2-(4-fluorophenyl)-3-methylsulfanyl-1-benzofuran (293 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 72%, m.p. 419-420 K; Rf = 0.67 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Structure description top

The title compound crystallizes ins the non-centrosymmetric space group Fdd2. The crystal studied was an inversion twin with a 0.85 (7) : 0.15 (7) domain ratio.

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (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. H atoms are presented as small spheres of arbitrary radius. The C10 atom of the cyclopentyl ring is disordered over two positions with site occupancy factors, from refinement of 0.617 (7 ) (part A) and 0.383 (7) (part B).
	Fig. 2. A view of the C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x -1/4 , - y + 1/4 , z - 1/4; (ii) x - 1/4, - y + 1/4, z - 1/4..]

5-Cyclopentyl-2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₂₀H₁₉FO₂S	F(000) = 2880
M_r = 342.41	D_x = 1.365 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 6619 reflections
a = 20.0254 (13) Å	θ = 2.4–27.7°
b = 33.197 (2) Å	µ = 0.21 mm⁻¹
c = 10.0233 (7) Å	T = 173 K
V = 6663.3 (8) Å³	Block, colourless
Z = 16	0.35 × 0.26 × 0.19 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4136 independent reflections
Radiation source: rotating anode	3915 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.034
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.4°
φ and ω scans	h = −26→23
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −44→42
T_min = 0.930, T_max = 0.961	l = −13→13
16962 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0576P)² + 8.9505P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4136 reflections	Δρ_max = 0.48 e Å⁻³
223 parameters	Δρ_min = −0.37 e Å⁻³
96 restraints	Absolute structure: Flack (1983), 1949 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.15 (7)

Crystal data top

C₂₀H₁₉FO₂S	V = 6663.3 (8) Å³
M_r = 342.41	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 20.0254 (13) Å	µ = 0.21 mm⁻¹
b = 33.197 (2) Å	T = 173 K
c = 10.0233 (7) Å	0.35 × 0.26 × 0.19 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4136 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3915 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.961	R_int = 0.034
16962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.106	Δρ_max = 0.48 e Å⁻³
S = 1.06	Δρ_min = −0.37 e Å⁻³
4136 reflections	Absolute structure: Flack (1983), 1949 Friedel pairs
223 parameters	Absolute structure parameter: 0.15 (7)
96 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
S1	0.28603 (2)	0.120706 (14)	0.30091 (12)	0.02721 (11)
F1	0.22523 (7)	0.07977 (4)	−0.34573 (18)	0.0441 (3)
O1	0.31307 (7)	0.21374 (4)	0.06022 (18)	0.0312 (3)
O2	0.33631 (8)	0.11882 (5)	0.4113 (2)	0.0370 (4)
C1	0.29639 (10)	0.16799 (6)	0.2227 (2)	0.0262 (4)
C2	0.32275 (10)	0.20417 (6)	0.2840 (2)	0.0290 (4)
C3	0.34184 (12)	0.21599 (7)	0.4113 (2)	0.0357 (5)
H3	0.3357	0.1984	0.4851	0.043*
C4	0.37027 (13)	0.25424 (8)	0.4294 (3)	0.0404 (5)
C5	0.37902 (12)	0.27952 (7)	0.3188 (3)	0.0396 (5)
H5	0.3988	0.3052	0.3320	0.048*
C6	0.36010 (12)	0.26866 (7)	0.1916 (3)	0.0374 (5)
H6	0.3658	0.2862	0.1175	0.045*
C7	0.33230 (11)	0.23083 (6)	0.1784 (2)	0.0305 (4)
C8	0.29208 (10)	0.17501 (6)	0.0893 (2)	0.0274 (4)
C9	0.39134 (15)	0.26922 (8)	0.5643 (3)	0.0533 (7)
H9A	0.4160	0.2951	0.5521	0.064*	0.617 (7)
H9B	0.4273	0.2883	0.5361	0.064*	0.383 (7)
C10A	0.33241 (16)	0.27685 (18)	0.6576 (2)	0.0594 (11)	0.617 (7)
H10A	0.3050	0.2997	0.6255	0.071*	0.617 (7)
H10B	0.3038	0.2526	0.6644	0.071*	0.617 (7)
C10B	0.3491 (5)	0.2980 (3)	0.64769 (16)	0.0594 (11)	0.383 (7)
H10C	0.3011	0.2945	0.6278	0.071*	0.383 (7)
H10D	0.3617	0.3263	0.6298	0.071*	0.383 (7)
C11	0.3643 (2)	0.28668 (11)	0.79210 (19)	0.0710 (10)
H11A	0.3745	0.3158	0.7992	0.085*	0.617 (7)
H11B	0.3346	0.2789	0.8667	0.085*	0.617 (7)
H11C	0.3704	0.3113	0.8466	0.085*	0.383 (7)
H11D	0.3269	0.2709	0.8301	0.085*	0.383 (7)
C12	0.42736 (18)	0.26191 (9)	0.7924 (3)	0.0585 (7)
H12A	0.4253	0.2407	0.8618	0.070*
H12B	0.4669	0.2791	0.8092	0.070*
C13	0.4306 (2)	0.24326 (13)	0.6533 (4)	0.0819 (13)
H13A	0.4775	0.2418	0.6223	0.098*
H13B	0.4118	0.2157	0.6546	0.098*
C14	0.27300 (10)	0.15066 (6)	−0.0241 (2)	0.0271 (4)
C15	0.22789 (11)	0.11913 (7)	−0.0111 (2)	0.0312 (4)
H15	0.2076	0.1141	0.0730	0.037*
C16	0.21211 (11)	0.09501 (7)	−0.1192 (2)	0.0338 (4)
H16	0.1819	0.0731	−0.1099	0.041*
C17	0.24099 (11)	0.10340 (7)	−0.2402 (2)	0.0318 (4)
C18	0.28529 (11)	0.13457 (7)	−0.2591 (2)	0.0349 (5)
H18	0.3042	0.1397	−0.3443	0.042*
C19	0.30136 (11)	0.15821 (7)	−0.1500 (2)	0.0326 (4)
H19	0.3320	0.1798	−0.1602	0.039*
C20	0.20733 (10)	0.13041 (8)	0.3791 (3)	0.0356 (5)
H20A	0.1952	0.1075	0.4359	0.053*
H20B	0.1730	0.1342	0.3105	0.053*
H20C	0.2107	0.1548	0.4337	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0302 (2)	0.0261 (2)	0.0254 (2)	0.00067 (19)	−0.00003 (18)	0.00238 (18)
F1	0.0492 (8)	0.0511 (8)	0.0321 (7)	−0.0062 (6)	−0.0020 (6)	−0.0098 (6)
O1	0.0371 (8)	0.0276 (7)	0.0290 (7)	−0.0008 (6)	0.0008 (6)	0.0027 (6)
O2	0.0312 (8)	0.0433 (9)	0.0365 (8)	0.0021 (7)	−0.0056 (6)	0.0111 (7)
C1	0.0253 (9)	0.0257 (9)	0.0277 (9)	0.0004 (7)	0.0014 (8)	0.0018 (7)
C2	0.0262 (9)	0.0265 (9)	0.0344 (10)	0.0029 (7)	0.0022 (8)	−0.0022 (7)
C3	0.0411 (12)	0.0342 (11)	0.0319 (10)	−0.0022 (9)	0.0019 (9)	−0.0036 (9)
C4	0.0419 (13)	0.0368 (11)	0.0425 (12)	−0.0004 (9)	0.0001 (10)	−0.0133 (9)
C5	0.0400 (12)	0.0279 (10)	0.0510 (14)	−0.0023 (9)	0.0008 (10)	−0.0085 (10)
C6	0.0383 (12)	0.0247 (9)	0.0492 (13)	0.0006 (8)	0.0032 (10)	0.0004 (8)
C7	0.0301 (10)	0.0277 (9)	0.0336 (10)	0.0036 (8)	0.0002 (7)	−0.0022 (8)
C8	0.0239 (9)	0.0288 (9)	0.0294 (10)	0.0018 (7)	0.0029 (7)	0.0033 (7)
C9	0.0850 (19)	0.0369 (11)	0.0381 (11)	−0.0150 (12)	0.0014 (12)	−0.0100 (10)
C10A	0.086 (2)	0.053 (3)	0.0391 (13)	0.0215 (19)	−0.0073 (13)	0.0017 (14)
C10B	0.086 (2)	0.053 (3)	0.0391 (13)	0.0215 (19)	−0.0073 (13)	0.0017 (14)
C11	0.108 (3)	0.071 (2)	0.0337 (10)	0.0304 (18)	−0.0064 (14)	−0.0035 (12)
C12	0.087 (2)	0.0503 (15)	0.0382 (13)	0.0047 (14)	−0.0166 (15)	0.0034 (12)
C13	0.086 (3)	0.096 (3)	0.064 (2)	0.046 (2)	−0.032 (2)	−0.032 (2)
C14	0.0247 (9)	0.0303 (9)	0.0261 (9)	0.0018 (7)	−0.0001 (7)	0.0017 (7)
C15	0.0275 (10)	0.0405 (11)	0.0256 (10)	−0.0026 (8)	0.0026 (8)	−0.0002 (8)
C16	0.0300 (10)	0.0366 (11)	0.0348 (11)	−0.0049 (8)	−0.0005 (8)	−0.0014 (9)
C17	0.0287 (10)	0.0396 (11)	0.0271 (10)	0.0032 (8)	−0.0026 (8)	−0.0040 (8)
C18	0.0359 (11)	0.0436 (12)	0.0253 (10)	0.0000 (9)	0.0018 (8)	0.0016 (9)
C19	0.0324 (11)	0.0368 (10)	0.0284 (9)	−0.0028 (8)	0.0031 (8)	0.0054 (8)
C20	0.0258 (10)	0.0486 (12)	0.0324 (11)	−0.0019 (9)	0.0010 (8)	0.0075 (9)

Geometric parameters (Å, º) top

S1—O2	1.4973 (16)	C10B—C11	1.5258 (14)
S1—C1	1.767 (2)	C10B—H10C	0.9900
S1—C20	1.789 (2)	C10B—H10D	0.9900
F1—C17	1.354 (2)	C11—C12	1.507 (5)
O1—C7	1.369 (3)	C11—H11A	0.9900
O1—C8	1.384 (2)	C11—H11B	0.9900
C1—C8	1.360 (3)	C11—H11C	0.9900
C1—C2	1.449 (3)	C11—H11D	0.9900
C2—C3	1.388 (3)	C12—C13	1.527 (4)
C2—C7	1.393 (3)	C12—H12A	0.9900
C3—C4	1.403 (3)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.402 (4)	C13—H13B	0.9900
C4—C9	1.501 (4)	C14—C15	1.389 (3)
C5—C6	1.378 (4)	C14—C19	1.406 (3)
C5—H5	0.9500	C15—C16	1.384 (3)
C6—C7	1.380 (3)	C15—H15	0.9500
C6—H6	0.9500	C16—C17	1.373 (3)
C8—C14	1.447 (3)	C16—H16	0.9500
C9—C13	1.469 (5)	C17—C18	1.376 (3)
C9—C10B	1.5249 (14)	C18—C19	1.384 (3)
C9—C10A	1.5272 (14)	C18—H18	0.9500
C9—H9A	1.0000	C19—H19	0.9500
C9—H9B	1.0000	C20—H20A	0.9800
C10A—C11	1.5266 (14)	C20—H20B	0.9800
C10A—H10A	0.9900	C20—H20C	0.9800
C10A—H10B	0.9900

O2—S1—C1	106.63 (9)	C12—C11—C10A	103.6 (3)
O2—S1—C20	106.03 (10)	C12—C11—H11A	111.0
C1—S1—C20	97.93 (10)	C10B—C11—H11A	82.5
C7—O1—C8	106.75 (15)	C10A—C11—H11A	111.0
C8—C1—C2	107.34 (18)	C12—C11—H11B	111.0
C8—C1—S1	125.54 (16)	C10B—C11—H11B	131.4
C2—C1—S1	126.22 (16)	C10A—C11—H11B	111.0
C3—C2—C7	118.73 (19)	H11A—C11—H11B	109.0
C3—C2—C1	136.4 (2)	C12—C11—H11C	110.2
C7—C2—C1	104.73 (18)	C10B—C11—H11C	110.2
C2—C3—C4	119.1 (2)	C10A—C11—H11C	135.7
C2—C3—H3	120.4	H11B—C11—H11C	82.8
C4—C3—H3	120.4	C12—C11—H11D	110.2
C5—C4—C3	119.3 (2)	C10B—C11—H11D	110.2
C5—C4—C9	118.6 (2)	C10A—C11—H11D	84.9
C3—C4—C9	122.0 (2)	H11A—C11—H11D	130.1
C6—C5—C4	122.7 (2)	H11C—C11—H11D	108.5
C6—C5—H5	118.6	C11—C12—C13	104.8 (2)
C4—C5—H5	118.6	C11—C12—H12A	110.8
C5—C6—C7	116.0 (2)	C13—C12—H12A	110.8
C5—C6—H6	122.0	C11—C12—H12B	110.8
C7—C6—H6	122.0	C13—C12—H12B	110.8
O1—C7—C6	125.0 (2)	H12A—C12—H12B	108.9
O1—C7—C2	110.83 (17)	C9—C13—C12	107.1 (3)
C6—C7—C2	124.1 (2)	C9—C13—H13A	110.3
C1—C8—O1	110.33 (18)	C12—C13—H13A	110.3
C1—C8—C14	133.92 (19)	C9—C13—H13B	110.3
O1—C8—C14	115.71 (17)	C12—C13—H13B	110.3
C13—C9—C4	120.2 (2)	H13A—C13—H13B	108.6
C13—C9—C10B	109.4 (2)	C15—C14—C19	118.79 (19)
C4—C9—C10B	123.1 (3)	C15—C14—C8	121.27 (18)
C13—C9—C10A	98.0 (3)	C19—C14—C8	119.93 (18)
C4—C9—C10A	112.9 (2)	C16—C15—C14	120.7 (2)
C13—C9—H9A	108.3	C16—C15—H15	119.6
C4—C9—H9A	108.3	C14—C15—H15	119.6
C10B—C9—H9A	78.6	C17—C16—C15	118.6 (2)
C10A—C9—H9A	108.3	C17—C16—H16	120.7
C13—C9—H9B	99.1	C15—C16—H16	120.7
C4—C9—H9B	99.1	F1—C17—C16	118.3 (2)
C10B—C9—H9B	99.1	F1—C17—C18	118.61 (18)
C10A—C9—H9B	128.7	C16—C17—C18	123.1 (2)
C11—C10A—C9	104.7 (2)	C17—C18—C19	117.9 (2)
C11—C10A—H10A	110.8	C17—C18—H18	121.1
C9—C10A—H10A	110.8	C19—C18—H18	121.1
C11—C10A—H10B	110.8	C18—C19—C14	120.9 (2)
C9—C10A—H10B	110.8	C18—C19—H19	119.5
H10A—C10A—H10B	108.9	C14—C19—H19	119.5
C9—C10B—C11	104.8 (2)	S1—C20—H20A	109.5
C9—C10B—H10C	110.8	S1—C20—H20B	109.5
C11—C10B—H10C	110.8	H20A—C20—H20B	109.5
C9—C10B—H10D	110.8	S1—C20—H20C	109.5
C11—C10B—H10D	110.8	H20A—C20—H20C	109.5
H10C—C10B—H10D	108.9	H20B—C20—H20C	109.5
C12—C11—C10B	107.6 (3)

O2—S1—C1—C8	141.47 (18)	C5—C4—C9—C10A	111.4 (3)
C20—S1—C1—C8	−109.11 (19)	C3—C4—C9—C10A	−68.1 (4)
O2—S1—C1—C2	−26.3 (2)	C13—C9—C10A—C11	45.6 (4)
C20—S1—C1—C2	83.13 (19)	C4—C9—C10A—C11	173.3 (3)
C8—C1—C2—C3	−176.1 (2)	C10B—C9—C10A—C11	−69.7 (3)
S1—C1—C2—C3	−6.5 (4)	C13—C9—C10B—C11	−1.6 (8)
C8—C1—C2—C7	0.1 (2)	C4—C9—C10B—C11	148.3 (4)
S1—C1—C2—C7	169.66 (15)	C10A—C9—C10B—C11	69.9 (3)
C7—C2—C3—C4	−0.2 (3)	C9—C10B—C11—C12	16.7 (8)
C1—C2—C3—C4	175.5 (2)	C9—C10B—C11—C10A	−70.0 (3)
C2—C3—C4—C5	−0.3 (4)	C9—C10A—C11—C12	−32.1 (4)
C2—C3—C4—C9	179.3 (2)	C9—C10A—C11—C10B	69.6 (3)
C3—C4—C5—C6	0.8 (4)	C10B—C11—C12—C13	−25.0 (6)
C9—C4—C5—C6	−178.8 (2)	C10A—C11—C12—C13	5.7 (4)
C4—C5—C6—C7	−0.7 (4)	C4—C9—C13—C12	−164.7 (3)
C8—O1—C7—C6	176.1 (2)	C10B—C9—C13—C12	−13.9 (6)
C8—O1—C7—C2	−1.3 (2)	C10A—C9—C13—C12	−42.3 (4)
C5—C6—C7—O1	−176.9 (2)	C11—C12—C13—C9	23.9 (4)
C5—C6—C7—C2	0.2 (3)	C1—C8—C14—C15	28.6 (3)
C3—C2—C7—O1	177.75 (19)	O1—C8—C14—C15	−154.06 (19)
C1—C2—C7—O1	0.8 (2)	C1—C8—C14—C19	−150.1 (2)
C3—C2—C7—C6	0.3 (3)	O1—C8—C14—C19	27.3 (3)
C1—C2—C7—C6	−176.7 (2)	C19—C14—C15—C16	1.3 (3)
C2—C1—C8—O1	−0.9 (2)	C8—C14—C15—C16	−177.3 (2)
S1—C1—C8—O1	−170.58 (14)	C14—C15—C16—C17	−1.2 (3)
C2—C1—C8—C14	176.6 (2)	C15—C16—C17—F1	−179.84 (19)
S1—C1—C8—C14	6.9 (3)	C15—C16—C17—C18	0.4 (4)
C7—O1—C8—C1	1.4 (2)	F1—C17—C18—C19	−179.4 (2)
C7—O1—C8—C14	−176.61 (17)	C16—C17—C18—C19	0.4 (3)
C5—C4—C9—C13	−133.7 (3)	C17—C18—C19—C14	−0.3 (3)
C3—C4—C9—C13	46.8 (4)	C15—C14—C19—C18	−0.5 (3)
C5—C4—C9—C10B	79.6 (6)	C8—C14—C19—C18	178.1 (2)
C3—C4—C9—C10B	−100.0 (6)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1/C2/C7/O/C8 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···O2ⁱ	0.98	2.29	3.262 (3)	169
C16—H16···Cgⁱ	0.95	2.53	3.365 (3)	146

Symmetry code: (i) x−1/4, −y+1/4, z−1/4.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉FO₂S
M_r	342.41
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	173
a, b, c (Å)	20.0254 (13), 33.197 (2), 10.0233 (7)
V (Å³)	6663.3 (8)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.35 × 0.26 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.930, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	16962, 4136, 3915
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.106, 1.06
No. of reflections	4136
No. of parameters	223
No. of restraints	96
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.37
Absolute structure	Flack (1983), 1949 Friedel pairs
Absolute structure parameter	0.15 (7)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1/C2/C7/O/C8 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···O2ⁱ	0.98	2.29	3.262 (3)	169.2
C16—H16···Cgⁱ	0.95	2.53	3.365 (3)	146.3

Symmetry code: (i) x−1/4, −y+1/4, z−1/4.

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res., 164, 191–195. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1167. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o470. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar

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