5-Cyclo­hexyl-2-(4-fluoro­phen­yl)-3-isopropyl­sulfonyl-1-benzofuran

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

doi:10.1107/S160053681101097X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o1001

doi:10.1107/S160053681101097X

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5-Cyclohexyl-2-(4-fluorophenyl)-3-isopropylsulfonyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^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 21 March 2011; accepted 24 March 2011; online 31 March 2011)

In the title compound, C₂₃H₂₅FO₂S, the cyclohexyl ring adopts a chair conformation. The 4-fluorophenyl ring makes a dihedral angle of 50.74 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by intermolecular C—H⋯π interactions.

Related literature

For the biological 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-aryl-5-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2011a ,b ).

Experimental

Crystal data

C₂₃H₂₅FO₃S
M_r = 400.49
Monoclinic, P 2₁ /c
a = 16.2065 (3) Å
b = 8.4993 (2) Å
c = 15.4031 (3) Å
β = 110.411 (1)°
V = 1988.47 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 173 K
0.35 × 0.25 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.935, T_max = 0.969
34421 measured reflections
4536 independent reflections
3857 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.118
S = 1.05
4536 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯Cgⁱ	0.99	2.68	3.667 (2)	172
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 datablocks global, I. DOI: 10.1107/S160053681101097X/ez2240sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101097X/ez2240Isup2.hkl

checkCIF report

Comment top

Many compounds having a benzofuran skeleton exhibit potent biological properties such as antibacterial, antifungal, antitumor, antiviral and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These compounds 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-aryl-5-cyclohexyl-3-methylsulfinyl-1-benzofuran analogues (Choi et al., 2011a, b), we report herein on the molecular and crystal structures of the title compound.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring makes a dihedral angle of 50.74 (4)° with the mean plane of the benzofuran fragment. The crystal packing is stabilized by intermolecular C—H···π interactions between a cyclohexyl H atom and the benzene ring (Table 1; C14—H14A···Cgⁱ, Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For the biological 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-aryl-5-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2011a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-(4-fluorophenyl)-3-isopropylsulfanyl-1-benzofuran (331 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, 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 (benzene) to afford the title compound as a colorless solid [yield 73%, m.p. 417–418 K; R_f = 0.66 (benzene)]. 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.

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.

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 a small spheres of arbitrary radius.

5-Cyclohexyl-2-(4-fluorophenyl)-3-isopropylsulfonyl-1-benzofuran top

Crystal data top

C₂₃H₂₅FO₃S	F(000) = 848
M_r = 400.49	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9904 reflections
a = 16.2065 (3) Å	θ = 2.7–27.5°
b = 8.4993 (2) Å	µ = 0.19 mm⁻¹
c = 15.4031 (3) Å	T = 173 K
β = 110.411 (1)°	Block, colourless
V = 1988.47 (7) Å³	0.35 × 0.25 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4536 independent reflections
Radiation source: rotating anode	3857 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.040
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.3°
ϕ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→10
T_min = 0.935, T_max = 0.969	l = −19→19
34421 measured reflections

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0616P)² + 0.8589P] where P = (F_o² + 2F_c²)/3
4536 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₃H₂₅FO₃S	V = 1988.47 (7) Å³
M_r = 400.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.2065 (3) Å	µ = 0.19 mm⁻¹
b = 8.4993 (2) Å	T = 173 K
c = 15.4031 (3) Å	0.35 × 0.25 × 0.16 mm
β = 110.411 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4536 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3857 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.969	R_int = 0.040
34421 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	Δρ_max = 0.43 e Å⁻³
4536 reflections	Δρ_min = −0.43 e Å⁻³
255 parameters

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
S1	0.19580 (2)	0.56351 (4)	0.11644 (2)	0.02585 (12)
F1	−0.06671 (7)	0.55451 (15)	0.39156 (8)	0.0526 (3)
O1	0.30601 (7)	0.43713 (13)	0.37816 (7)	0.0286 (2)
O2	0.12420 (7)	0.65463 (14)	0.12504 (8)	0.0355 (3)
O3	0.25519 (7)	0.63717 (14)	0.07757 (8)	0.0337 (3)
C1	0.26010 (9)	0.49468 (18)	0.22631 (10)	0.0250 (3)
C2	0.35310 (10)	0.45605 (17)	0.25534 (10)	0.0254 (3)
C3	0.41687 (10)	0.44682 (18)	0.21347 (10)	0.0271 (3)
H3	0.4025	0.4723	0.1498	0.032*
C4	0.50184 (10)	0.39963 (18)	0.26662 (11)	0.0288 (3)
C5	0.52195 (10)	0.3651 (2)	0.36117 (11)	0.0336 (4)
H5	0.5802	0.3333	0.3967	0.040*
C6	0.46071 (10)	0.3755 (2)	0.40410 (11)	0.0330 (3)
H6	0.4751	0.3522	0.4680	0.040*
C7	0.37701 (10)	0.42184 (18)	0.34923 (10)	0.0269 (3)
C8	0.23549 (10)	0.48094 (18)	0.30212 (10)	0.0262 (3)
C9	0.57531 (10)	0.38349 (19)	0.22780 (11)	0.0311 (3)
H9	0.6053	0.2810	0.2506	0.037*
C10	0.54480 (11)	0.3797 (3)	0.12306 (12)	0.0440 (4)
H10A	0.5145	0.4796	0.0978	0.053*
H10B	0.5022	0.2927	0.0996	0.053*
C11	0.62254 (12)	0.3564 (3)	0.08978 (14)	0.0464 (5)
H11A	0.6502	0.2530	0.1113	0.056*
H11B	0.6010	0.3567	0.0212	0.056*
C12	0.69027 (13)	0.4850 (3)	0.12594 (15)	0.0476 (5)
H12A	0.6644	0.5871	0.0989	0.057*
H12B	0.7413	0.4637	0.1064	0.057*
C13	0.72119 (13)	0.4951 (3)	0.23060 (16)	0.0555 (5)
H13A	0.7613	0.5862	0.2518	0.067*
H13B	0.7546	0.3988	0.2576	0.067*
C14	0.64422 (12)	0.5131 (2)	0.26502 (13)	0.0426 (4)
H14A	0.6161	0.6168	0.2454	0.051*
H14B	0.6666	0.5100	0.3336	0.051*
C15	0.15393 (10)	0.50362 (18)	0.32210 (10)	0.0274 (3)
C16	0.07583 (11)	0.4297 (2)	0.26997 (11)	0.0357 (4)
H16	0.0737	0.3676	0.2180	0.043*
C17	0.00085 (11)	0.4459 (2)	0.29324 (12)	0.0400 (4)
H17	−0.0527	0.3954	0.2580	0.048*
C18	0.00630 (11)	0.5370 (2)	0.36879 (12)	0.0360 (4)
C19	0.08251 (12)	0.6103 (2)	0.42288 (12)	0.0367 (4)
H19	0.0841	0.6712	0.4752	0.044*
C20	0.15689 (11)	0.5932 (2)	0.39912 (11)	0.0320 (3)
H20	0.2103	0.6428	0.4355	0.038*
C21	0.14993 (10)	0.3924 (2)	0.04907 (11)	0.0321 (3)
H21	0.1114	0.3382	0.0783	0.039*
C22	0.09234 (11)	0.4450 (2)	−0.04767 (11)	0.0408 (4)
H22A	0.1294	0.4911	−0.0795	0.061*
H22B	0.0499	0.5237	−0.0429	0.061*
H22C	0.0606	0.3541	−0.0828	0.061*
C23	0.22097 (13)	0.2779 (2)	0.04729 (13)	0.0449 (4)
H23A	0.1936	0.1838	0.0123	0.067*
H23B	0.2565	0.2482	0.1108	0.067*
H23C	0.2588	0.3278	0.0176	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02457 (19)	0.0289 (2)	0.02323 (19)	0.00035 (14)	0.00727 (14)	0.00259 (14)
F1	0.0401 (6)	0.0691 (8)	0.0599 (7)	0.0072 (5)	0.0317 (5)	−0.0005 (6)
O1	0.0284 (5)	0.0351 (6)	0.0225 (5)	0.0022 (4)	0.0092 (4)	0.0014 (4)
O2	0.0306 (6)	0.0400 (6)	0.0352 (6)	0.0087 (5)	0.0105 (5)	0.0045 (5)
O3	0.0323 (6)	0.0383 (6)	0.0308 (6)	−0.0037 (5)	0.0114 (5)	0.0073 (5)
C1	0.0246 (7)	0.0265 (7)	0.0239 (7)	−0.0002 (6)	0.0083 (5)	−0.0001 (6)
C2	0.0259 (7)	0.0245 (7)	0.0237 (7)	−0.0011 (5)	0.0060 (6)	−0.0024 (6)
C3	0.0274 (7)	0.0289 (7)	0.0245 (7)	−0.0022 (6)	0.0085 (6)	−0.0026 (6)
C4	0.0254 (7)	0.0289 (7)	0.0309 (8)	−0.0024 (6)	0.0085 (6)	−0.0040 (6)
C5	0.0262 (7)	0.0378 (9)	0.0314 (8)	0.0009 (6)	0.0035 (6)	−0.0015 (7)
C6	0.0328 (8)	0.0373 (9)	0.0246 (7)	0.0018 (7)	0.0047 (6)	0.0008 (6)
C7	0.0276 (7)	0.0278 (7)	0.0259 (7)	−0.0010 (6)	0.0099 (6)	−0.0027 (6)
C8	0.0276 (7)	0.0255 (7)	0.0243 (7)	−0.0002 (6)	0.0075 (6)	−0.0010 (6)
C9	0.0269 (7)	0.0274 (8)	0.0387 (8)	0.0003 (6)	0.0109 (6)	0.0009 (7)
C10	0.0317 (8)	0.0627 (12)	0.0408 (9)	−0.0071 (8)	0.0168 (7)	−0.0154 (9)
C11	0.0415 (10)	0.0555 (12)	0.0514 (11)	−0.0043 (9)	0.0278 (8)	−0.0123 (9)
C12	0.0436 (10)	0.0474 (11)	0.0614 (12)	−0.0017 (8)	0.0304 (9)	0.0042 (10)
C13	0.0354 (10)	0.0700 (14)	0.0628 (13)	−0.0184 (10)	0.0193 (9)	−0.0085 (11)
C14	0.0360 (9)	0.0482 (10)	0.0440 (10)	−0.0148 (8)	0.0143 (8)	−0.0112 (8)
C15	0.0305 (7)	0.0289 (7)	0.0246 (7)	0.0011 (6)	0.0122 (6)	0.0019 (6)
C16	0.0345 (8)	0.0464 (10)	0.0280 (8)	−0.0034 (7)	0.0132 (7)	−0.0063 (7)
C17	0.0307 (8)	0.0544 (11)	0.0346 (9)	−0.0046 (8)	0.0110 (7)	−0.0023 (8)
C18	0.0333 (8)	0.0422 (9)	0.0387 (9)	0.0074 (7)	0.0204 (7)	0.0064 (7)
C19	0.0444 (9)	0.0350 (9)	0.0370 (9)	0.0030 (7)	0.0223 (7)	−0.0034 (7)
C20	0.0343 (8)	0.0330 (8)	0.0304 (8)	−0.0023 (7)	0.0135 (6)	−0.0033 (7)
C21	0.0332 (8)	0.0369 (8)	0.0255 (7)	−0.0078 (7)	0.0094 (6)	−0.0034 (7)
C22	0.0298 (8)	0.0606 (12)	0.0275 (8)	−0.0037 (8)	0.0044 (6)	−0.0036 (8)
C23	0.0535 (11)	0.0387 (10)	0.0366 (9)	0.0040 (8)	0.0084 (8)	−0.0087 (8)

Geometric parameters (Å, º) top

S1—O2	1.4391 (11)	C11—H11B	0.9900
S1—O3	1.4417 (11)	C12—C13	1.515 (3)
S1—C1	1.7498 (15)	C12—H12A	0.9900
S1—C21	1.7910 (16)	C12—H12B	0.9900
F1—C18	1.3545 (18)	C13—C14	1.524 (3)
O1—C8	1.3722 (17)	C13—H13A	0.9900
O1—C7	1.3774 (17)	C13—H13B	0.9900
C1—C8	1.364 (2)	C14—H14A	0.9900
C1—C2	1.452 (2)	C14—H14B	0.9900
C2—C7	1.391 (2)	C15—C16	1.390 (2)
C2—C3	1.398 (2)	C15—C20	1.396 (2)
C3—C4	1.393 (2)	C16—C17	1.388 (2)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.408 (2)	C17—C18	1.375 (3)
C4—C9	1.513 (2)	C17—H17	0.9500
C5—C6	1.374 (2)	C18—C19	1.375 (3)
C5—H5	0.9500	C19—C20	1.384 (2)
C6—C7	1.382 (2)	C19—H19	0.9500
C6—H6	0.9500	C20—H20	0.9500
C8—C15	1.471 (2)	C21—C23	1.515 (2)
C9—C10	1.514 (2)	C21—C22	1.524 (2)
C9—C14	1.531 (2)	C21—H21	1.0000
C9—H9	1.0000	C22—H22A	0.9800
C10—C11	1.530 (2)	C22—H22B	0.9800
C10—H10A	0.9900	C22—H22C	0.9800
C10—H10B	0.9900	C23—H23A	0.9800
C11—C12	1.511 (3)	C23—H23B	0.9800
C11—H11A	0.9900	C23—H23C	0.9800

O2—S1—O3	118.75 (7)	C11—C12—H12B	109.4
O2—S1—C1	108.56 (7)	C13—C12—H12B	109.4
O3—S1—C1	106.75 (7)	H12A—C12—H12B	108.0
O2—S1—C21	107.78 (7)	C12—C13—C14	111.65 (17)
O3—S1—C21	108.32 (7)	C12—C13—H13A	109.3
C1—S1—C21	106.00 (7)	C14—C13—H13A	109.3
C8—O1—C7	106.89 (11)	C12—C13—H13B	109.3
C8—C1—C2	107.39 (13)	C14—C13—H13B	109.3
C8—C1—S1	127.10 (12)	H13A—C13—H13B	108.0
C2—C1—S1	125.27 (11)	C13—C14—C9	112.12 (16)
C7—C2—C3	119.02 (13)	C13—C14—H14A	109.2
C7—C2—C1	104.49 (13)	C9—C14—H14A	109.2
C3—C2—C1	136.49 (14)	C13—C14—H14B	109.2
C4—C3—C2	118.89 (14)	C9—C14—H14B	109.2
C4—C3—H3	120.6	H14A—C14—H14B	107.9
C2—C3—H3	120.6	C16—C15—C20	119.46 (14)
C3—C4—C5	119.52 (14)	C16—C15—C8	121.58 (14)
C3—C4—C9	123.13 (14)	C20—C15—C8	118.82 (14)
C5—C4—C9	117.35 (14)	C17—C16—C15	120.57 (15)
C6—C5—C4	122.60 (14)	C17—C16—H16	119.7
C6—C5—H5	118.7	C15—C16—H16	119.7
C4—C5—H5	118.7	C18—C17—C16	118.08 (16)
C5—C6—C7	116.35 (14)	C18—C17—H17	121.0
C5—C6—H6	121.8	C16—C17—H17	121.0
C7—C6—H6	121.8	F1—C18—C17	118.50 (16)
O1—C7—C6	125.56 (14)	F1—C18—C19	118.33 (15)
O1—C7—C2	110.82 (13)	C17—C18—C19	123.17 (16)
C6—C7—C2	123.60 (14)	C18—C19—C20	118.24 (15)
C1—C8—O1	110.41 (13)	C18—C19—H19	120.9
C1—C8—C15	136.08 (14)	C20—C19—H19	120.9
O1—C8—C15	113.50 (12)	C19—C20—C15	120.46 (15)
C4—C9—C10	114.42 (13)	C19—C20—H20	119.8
C4—C9—C14	111.02 (14)	C15—C20—H20	119.8
C10—C9—C14	109.81 (15)	C23—C21—C22	112.41 (14)
C4—C9—H9	107.1	C23—C21—S1	111.55 (11)
C10—C9—H9	107.1	C22—C21—S1	108.49 (12)
C14—C9—H9	107.1	C23—C21—H21	108.1
C9—C10—C11	111.03 (15)	C22—C21—H21	108.1
C9—C10—H10A	109.4	S1—C21—H21	108.1
C11—C10—H10A	109.4	C21—C22—H22A	109.5
C9—C10—H10B	109.4	C21—C22—H22B	109.5
C11—C10—H10B	109.4	H22A—C22—H22B	109.5
H10A—C10—H10B	108.0	C21—C22—H22C	109.5
C12—C11—C10	111.13 (16)	H22A—C22—H22C	109.5
C12—C11—H11A	109.4	H22B—C22—H22C	109.5
C10—C11—H11A	109.4	C21—C23—H23A	109.5
C12—C11—H11B	109.4	C21—C23—H23B	109.5
C10—C11—H11B	109.4	H23A—C23—H23B	109.5
H11A—C11—H11B	108.0	C21—C23—H23C	109.5
C11—C12—C13	111.19 (16)	H23A—C23—H23C	109.5
C11—C12—H12A	109.4	H23B—C23—H23C	109.5
C13—C12—H12A	109.4

O2—S1—C1—C8	20.02 (16)	C5—C4—C9—C10	164.58 (16)
O3—S1—C1—C8	149.13 (14)	C3—C4—C9—C14	109.38 (17)
C21—S1—C1—C8	−95.53 (15)	C5—C4—C9—C14	−70.45 (19)
O2—S1—C1—C2	−153.56 (13)	C4—C9—C10—C11	−177.68 (15)
O3—S1—C1—C2	−24.45 (15)	C14—C9—C10—C11	56.7 (2)
C21—S1—C1—C2	90.89 (14)	C9—C10—C11—C12	−57.9 (2)
C8—C1—C2—C7	−0.18 (17)	C10—C11—C12—C13	55.8 (2)
S1—C1—C2—C7	174.46 (11)	C11—C12—C13—C14	−53.9 (2)
C8—C1—C2—C3	179.77 (17)	C12—C13—C14—C9	54.0 (2)
S1—C1—C2—C3	−5.6 (3)	C4—C9—C14—C13	177.30 (16)
C7—C2—C3—C4	1.7 (2)	C10—C9—C14—C13	−55.2 (2)
C1—C2—C3—C4	−178.29 (16)	C1—C8—C15—C16	53.2 (3)
C2—C3—C4—C5	−1.1 (2)	O1—C8—C15—C16	−128.01 (16)
C2—C3—C4—C9	179.09 (14)	C1—C8—C15—C20	−131.11 (19)
C3—C4—C5—C6	0.1 (3)	O1—C8—C15—C20	47.7 (2)
C9—C4—C5—C6	179.98 (15)	C20—C15—C16—C17	0.8 (3)
C4—C5—C6—C7	0.2 (3)	C8—C15—C16—C17	176.42 (16)
C8—O1—C7—C6	−178.35 (15)	C15—C16—C17—C18	0.2 (3)
C8—O1—C7—C2	0.27 (17)	C16—C17—C18—F1	179.46 (16)
C5—C6—C7—O1	178.87 (15)	C16—C17—C18—C19	−1.1 (3)
C5—C6—C7—C2	0.4 (2)	F1—C18—C19—C20	−179.56 (15)
C3—C2—C7—O1	179.99 (13)	C17—C18—C19—C20	1.0 (3)
C1—C2—C7—O1	−0.06 (17)	C18—C19—C20—C15	0.0 (3)
C3—C2—C7—C6	−1.4 (2)	C16—C15—C20—C19	−0.9 (2)
C1—C2—C7—C6	178.59 (15)	C8—C15—C20—C19	−176.63 (15)
C2—C1—C8—O1	0.36 (17)	O2—S1—C21—C23	−172.18 (12)
S1—C1—C8—O1	−174.15 (11)	O3—S1—C21—C23	58.15 (14)
C2—C1—C8—C15	179.15 (17)	C1—S1—C21—C23	−56.11 (14)
S1—C1—C8—C15	4.6 (3)	O2—S1—C21—C22	63.47 (12)
C7—O1—C8—C1	−0.39 (17)	O3—S1—C21—C22	−66.20 (12)
C7—O1—C8—C15	−179.48 (12)	C1—S1—C21—C22	179.55 (11)
C3—C4—C9—C10	−15.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cgⁱ	0.99	2.68	3.667 (2)	172

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₅FO₃S
M_r	400.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	16.2065 (3), 8.4993 (2), 15.4031 (3)
β (°)	110.411 (1)
V (Å³)	1988.47 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.35 × 0.25 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.935, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	34421, 4536, 3857
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 1.05
No. of reflections	4536
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.43

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···Cgⁱ	0.99	2.68	3.667 (2)	172

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

References

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Volume 67| Part 4| April 2011| Page o1001

doi:10.1107/S160053681101097X

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