5-Cyclo­hexyl-3-(4-fluoro­phenyl­sulfin­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811007112

5-Cyclohexyl-3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran

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

In the title compound, C₂₁H₂₁FO₂S, the cyclohexyl ring adopts a chair conformation. The 4-fluorophenyl ring makes a dihedral angle of 83.55 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through weak intermolecular C—H

O and C—H

π interactions. The crystal structure also exhibits aromatic π–π interactions between the furan rings of neighbouring molecules [centroid–centroid distance = 3.541 (2) Å].

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811007112/zq2090sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811007112/zq2090Isup2.hkl Contains datablock I

CCDC reference: 820118

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.040
wR factor = 0.111
Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.19
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         11

Alert level G
PLAT153_ALERT_1_G The su's on the Cell Axes   are Equal (x 100000)         20 Ang.
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        100 Deg.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Many compounds having a benzofuran skeleton have attracted much attention owing to their interesting pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c), we report here on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The dihedral angle formed by the mean plane of the benzofuran ring and the 4-fluorophenyl ring is 83.55 (4)°. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a 4-fluorophenyl H atom and the furan O atom (Table 1; C20—H20···O1ⁱ), and the second one between a 4-fluorophenyl H atom and the oxygen of the S═O unit (Table 1; C21-H21···O2ⁱⁱ). The molecular packing (Fig. 3) is further stabilized by intermolecular C—H···π interactions; the first one between a cyclohexyl H atom and the benzene ring (Table 1; C10—H10B···Cg1ⁱⁱⁱ), and the second one between a methyl H atom and the benzene ring (Table 1; C15—H15C···Cg1^iv, Cg1 is the centroid of the C2–C7 benzene ring). The molecular packing (Fig. 3) also exhibits aromatic π–π interactions between the furan rings of neighbouring molecules, with a Cg2···Cg2^iv distance of 3.541 (2) ° (Cg2 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. (2006); 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 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b,c).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (306 mg, 0.9 mmol) in dichloromethane (40 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 422–423 K; R_f = 0.59 (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.

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 a small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x + 1, y, z ; (ii) - x + 1, - y + 1, - z + 1; (v) x - 1, y, z ]
	Fig. 3. A view of the C—H···π and π–π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (iii) - x + 1, - y, - z + 1; (iv) - x, - y + 1, - z + 1.]

5-Cyclohexyl-3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran top

Crystal data top

C₂₁H₂₁FO₂S	Z = 2
M_r = 356.44	F(000) = 376
Triclinic, P1	D_x = 1.327 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2531 (2) Å	Cell parameters from 6765 reflections
b = 10.1934 (2) Å	θ = 2.6–27.3°
c = 10.8151 (2) Å	µ = 0.20 mm⁻¹
α = 81.127 (1)°	T = 173 K
β = 66.716 (1)°	Block, colourless
γ = 72.248 (1)°	0.29 × 0.23 × 0.18 mm
V = 891.73 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	4073 independent reflections
Radiation source: rotating anode	3436 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→12
T_min = 0.943, T_max = 0.964	l = −14→14
15790 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.111	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0539P)² + 0.3464P] where P = (F_o² + 2F_c²)/3
4073 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₁H₂₁FO₂S	γ = 72.248 (1)°
M_r = 356.44	V = 891.73 (3) Å³
Triclinic, P1	Z = 2
a = 9.2531 (2) Å	Mo Kα radiation
b = 10.1934 (2) Å	µ = 0.20 mm⁻¹
c = 10.8151 (2) Å	T = 173 K
α = 81.127 (1)°	0.29 × 0.23 × 0.18 mm
β = 66.716 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4073 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3436 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.964	R_int = 0.027
15790 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.04	Δρ_max = 0.60 e Å⁻³
4073 reflections	Δρ_min = −0.27 e Å⁻³
227 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	0.16989 (5)	0.52226 (4)	0.70879 (4)	0.03038 (12)
F1	0.60813 (14)	0.09572 (12)	0.92500 (12)	0.0523 (3)
O1	−0.06925 (13)	0.32462 (11)	0.60921 (11)	0.0329 (3)
O2	0.27322 (16)	0.59605 (12)	0.59571 (12)	0.0426 (3)
C1	0.10554 (18)	0.41527 (15)	0.64093 (14)	0.0273 (3)
C2	0.19912 (18)	0.32226 (15)	0.53060 (14)	0.0264 (3)
C3	0.36263 (18)	0.27915 (15)	0.44540 (14)	0.0280 (3)
H3	0.4427	0.3139	0.4534	0.034*
C4	0.40637 (19)	0.18409 (15)	0.34828 (15)	0.0298 (3)
C5	0.2851 (2)	0.13569 (17)	0.33787 (16)	0.0355 (4)
H5	0.3163	0.0712	0.2711	0.043*
C6	0.1226 (2)	0.17765 (18)	0.42034 (16)	0.0361 (4)
H6	0.0417	0.1445	0.4118	0.043*
C7	0.08481 (18)	0.27058 (16)	0.51576 (15)	0.0293 (3)
C8	−0.05259 (18)	0.41298 (16)	0.68288 (15)	0.0299 (3)
C9	0.5826 (2)	0.13384 (16)	0.25508 (15)	0.0321 (3)
H9	0.5877	0.0668	0.1940	0.038*
C10	0.6938 (2)	0.05807 (19)	0.33242 (18)	0.0459 (5)
H10A	0.6882	0.1212	0.3961	0.055*
H10B	0.6547	−0.0210	0.3854	0.055*
C11	0.8704 (2)	0.00624 (19)	0.23672 (18)	0.0466 (5)
H11A	0.9398	−0.0392	0.2896	0.056*
H11B	0.8775	−0.0630	0.1781	0.056*
C12	0.9333 (2)	0.12360 (18)	0.15011 (18)	0.0395 (4)
H12A	1.0456	0.0863	0.0854	0.047*
H12B	0.9376	0.1875	0.2080	0.047*
C13	0.8246 (2)	0.20204 (18)	0.07324 (16)	0.0374 (4)
H13A	0.8325	0.1414	0.0063	0.045*
H13B	0.8637	0.2823	0.0238	0.045*
C14	0.64620 (19)	0.25206 (16)	0.16682 (15)	0.0323 (3)
H14A	0.5785	0.2953	0.1122	0.039*
H14B	0.6358	0.3229	0.2252	0.039*
C15	−0.20513 (19)	0.48483 (18)	0.78899 (17)	0.0375 (4)
H15A	−0.1830	0.5534	0.8284	0.056*
H15B	−0.2460	0.4176	0.8593	0.056*
H15C	−0.2874	0.5310	0.7494	0.056*
C16	0.30487 (18)	0.39021 (16)	0.77290 (15)	0.0285 (3)
C17	0.2397 (2)	0.32608 (18)	0.89640 (16)	0.0358 (4)
H17	0.1250	0.3507	0.9451	0.043*
C18	0.3418 (2)	0.22589 (19)	0.94899 (17)	0.0407 (4)
H18	0.2994	0.1806	1.0337	0.049*
C19	0.5066 (2)	0.19413 (17)	0.87463 (18)	0.0364 (4)
C20	0.5741 (2)	0.25692 (19)	0.75227 (18)	0.0392 (4)
H20	0.6888	0.2315	0.7036	0.047*
C21	0.4712 (2)	0.35849 (18)	0.70112 (16)	0.0351 (4)
H21	0.5145	0.4056	0.6178	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0334 (2)	0.0275 (2)	0.0277 (2)	−0.00806 (15)	−0.00769 (15)	−0.00389 (14)
F1	0.0523 (7)	0.0492 (6)	0.0629 (7)	−0.0050 (5)	−0.0358 (6)	−0.0011 (5)
O1	0.0274 (5)	0.0389 (6)	0.0319 (6)	−0.0104 (5)	−0.0102 (5)	0.0006 (5)
O2	0.0499 (7)	0.0381 (7)	0.0400 (7)	−0.0193 (6)	−0.0135 (6)	0.0048 (5)
C1	0.0260 (7)	0.0268 (7)	0.0251 (7)	−0.0044 (6)	−0.0074 (6)	−0.0011 (6)
C2	0.0294 (7)	0.0244 (7)	0.0235 (7)	−0.0064 (6)	−0.0093 (6)	0.0012 (5)
C3	0.0289 (7)	0.0280 (7)	0.0258 (7)	−0.0079 (6)	−0.0088 (6)	−0.0006 (6)
C4	0.0351 (8)	0.0260 (7)	0.0236 (7)	−0.0072 (6)	−0.0072 (6)	0.0004 (6)
C5	0.0473 (9)	0.0323 (8)	0.0286 (8)	−0.0125 (7)	−0.0132 (7)	−0.0044 (6)
C6	0.0405 (9)	0.0399 (9)	0.0351 (8)	−0.0173 (7)	−0.0170 (7)	−0.0008 (7)
C7	0.0286 (7)	0.0317 (8)	0.0265 (7)	−0.0081 (6)	−0.0098 (6)	0.0008 (6)
C8	0.0297 (8)	0.0296 (8)	0.0265 (7)	−0.0050 (6)	−0.0098 (6)	0.0022 (6)
C9	0.0369 (8)	0.0276 (8)	0.0250 (7)	−0.0063 (6)	−0.0047 (6)	−0.0054 (6)
C10	0.0420 (10)	0.0397 (9)	0.0323 (8)	0.0052 (8)	−0.0037 (7)	0.0052 (7)
C11	0.0400 (10)	0.0386 (9)	0.0391 (9)	0.0067 (8)	−0.0053 (8)	0.0003 (8)
C12	0.0348 (9)	0.0389 (9)	0.0386 (9)	−0.0017 (7)	−0.0113 (7)	−0.0068 (7)
C13	0.0350 (9)	0.0406 (9)	0.0314 (8)	−0.0106 (7)	−0.0082 (7)	0.0028 (7)
C14	0.0340 (8)	0.0319 (8)	0.0281 (7)	−0.0071 (6)	−0.0106 (6)	0.0006 (6)
C15	0.0272 (8)	0.0412 (9)	0.0345 (8)	−0.0037 (7)	−0.0064 (7)	0.0003 (7)
C16	0.0297 (7)	0.0307 (8)	0.0261 (7)	−0.0107 (6)	−0.0081 (6)	−0.0050 (6)
C17	0.0308 (8)	0.0447 (9)	0.0283 (8)	−0.0121 (7)	−0.0060 (6)	−0.0007 (7)
C18	0.0434 (10)	0.0471 (10)	0.0320 (8)	−0.0160 (8)	−0.0139 (7)	0.0048 (7)
C19	0.0393 (9)	0.0334 (8)	0.0443 (9)	−0.0081 (7)	−0.0233 (8)	−0.0051 (7)
C20	0.0272 (8)	0.0452 (10)	0.0456 (10)	−0.0117 (7)	−0.0095 (7)	−0.0096 (8)
C21	0.0325 (8)	0.0400 (9)	0.0315 (8)	−0.0159 (7)	−0.0056 (7)	−0.0022 (7)

Geometric parameters (Å, º) top

S1—O2	1.4852 (12)	C11—C12	1.515 (3)
S1—C1	1.7524 (16)	C11—H11A	0.9900
S1—C16	1.7956 (16)	C11—H11B	0.9900
F1—C19	1.3588 (19)	C12—C13	1.519 (2)
O1—C8	1.3685 (19)	C12—H12A	0.9900
O1—C7	1.3824 (18)	C12—H12B	0.9900
C1—C8	1.356 (2)	C13—C14	1.528 (2)
C1—C2	1.450 (2)	C13—H13A	0.9900
C2—C7	1.386 (2)	C13—H13B	0.9900
C2—C3	1.396 (2)	C14—H14A	0.9900
C3—C4	1.395 (2)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.403 (2)	C15—H15B	0.9800
C4—C9	1.513 (2)	C15—H15C	0.9800
C5—C6	1.380 (2)	C16—C21	1.380 (2)
C5—H5	0.9500	C16—C17	1.382 (2)
C6—C7	1.378 (2)	C17—C18	1.385 (2)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.481 (2)	C18—C19	1.373 (2)
C9—C14	1.531 (2)	C18—H18	0.9500
C9—C10	1.533 (2)	C19—C20	1.371 (2)
C9—H9	1.0000	C20—C21	1.387 (2)
C10—C11	1.525 (2)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500
C10—H10B	0.9900

O2—S1—C1	108.26 (7)	C10—C11—H11B	109.4
O2—S1—C16	106.99 (7)	H11A—C11—H11B	108.0
C1—S1—C16	98.14 (7)	C11—C12—C13	111.33 (15)
C8—O1—C7	106.48 (11)	C11—C12—H12A	109.4
C8—C1—C2	107.33 (14)	C13—C12—H12A	109.4
C8—C1—S1	123.11 (12)	C11—C12—H12B	109.4
C2—C1—S1	129.47 (11)	C13—C12—H12B	109.4
C7—C2—C3	119.30 (14)	H12A—C12—H12B	108.0
C7—C2—C1	104.57 (13)	C12—C13—C14	111.94 (13)
C3—C2—C1	136.13 (14)	C12—C13—H13A	109.2
C4—C3—C2	118.81 (14)	C14—C13—H13A	109.2
C4—C3—H3	120.6	C12—C13—H13B	109.2
C2—C3—H3	120.6	C14—C13—H13B	109.2
C3—C4—C5	119.29 (14)	H13A—C13—H13B	107.9
C3—C4—C9	120.33 (14)	C13—C14—C9	111.75 (13)
C5—C4—C9	120.38 (14)	C13—C14—H14A	109.3
C6—C5—C4	122.88 (15)	C9—C14—H14A	109.3
C6—C5—H5	118.6	C13—C14—H14B	109.3
C4—C5—H5	118.6	C9—C14—H14B	109.3
C7—C6—C5	116.01 (15)	H14A—C14—H14B	107.9
C7—C6—H6	122.0	C8—C15—H15A	109.5
C5—C6—H6	122.0	C8—C15—H15B	109.5
C6—C7—O1	125.54 (14)	H15A—C15—H15B	109.5
C6—C7—C2	123.71 (15)	C8—C15—H15C	109.5
O1—C7—C2	110.75 (13)	H15A—C15—H15C	109.5
C1—C8—O1	110.86 (13)	H15B—C15—H15C	109.5
C1—C8—C15	133.48 (16)	C21—C16—C17	121.34 (15)
O1—C8—C15	115.66 (14)	C21—C16—S1	119.74 (12)
C4—C9—C14	111.53 (13)	C17—C16—S1	118.87 (12)
C4—C9—C10	112.00 (13)	C16—C17—C18	119.85 (15)
C14—C9—C10	110.18 (14)	C16—C17—H17	120.1
C4—C9—H9	107.6	C18—C17—H17	120.1
C14—C9—H9	107.6	C19—C18—C17	117.80 (15)
C10—C9—H9	107.6	C19—C18—H18	121.1
C11—C10—C9	111.25 (14)	C17—C18—H18	121.1
C11—C10—H10A	109.4	F1—C19—C20	118.26 (15)
C9—C10—H10A	109.4	F1—C19—C18	118.36 (16)
C11—C10—H10B	109.4	C20—C19—C18	123.37 (16)
C9—C10—H10B	109.4	C19—C20—C21	118.46 (15)
H10A—C10—H10B	108.0	C19—C20—H20	120.8
C12—C11—C10	111.13 (14)	C21—C20—H20	120.8
C12—C11—H11A	109.4	C16—C21—C20	119.14 (15)
C10—C11—H11A	109.4	C16—C21—H21	120.4
C12—C11—H11B	109.4	C20—C21—H21	120.4

O2—S1—C1—C8	−130.14 (13)	C7—O1—C8—C15	179.16 (12)
C16—S1—C1—C8	118.88 (13)	C3—C4—C9—C14	−62.29 (18)
O2—S1—C1—C2	46.04 (15)	C5—C4—C9—C14	117.66 (16)
C16—S1—C1—C2	−64.95 (14)	C3—C4—C9—C10	61.72 (19)
C8—C1—C2—C7	−0.05 (16)	C5—C4—C9—C10	−118.33 (17)
S1—C1—C2—C7	−176.70 (12)	C4—C9—C10—C11	179.11 (15)
C8—C1—C2—C3	179.74 (16)	C14—C9—C10—C11	−56.1 (2)
S1—C1—C2—C3	3.1 (3)	C9—C10—C11—C12	57.1 (2)
C7—C2—C3—C4	−0.5 (2)	C10—C11—C12—C13	−55.7 (2)
C1—C2—C3—C4	179.69 (15)	C11—C12—C13—C14	54.27 (19)
C2—C3—C4—C5	0.7 (2)	C12—C13—C14—C9	−54.08 (19)
C2—C3—C4—C9	−179.37 (13)	C4—C9—C14—C13	179.57 (13)
C3—C4—C5—C6	−0.2 (2)	C10—C9—C14—C13	54.54 (18)
C9—C4—C5—C6	179.83 (15)	O2—S1—C16—C21	−11.66 (15)
C4—C5—C6—C7	−0.4 (2)	C1—S1—C16—C21	100.35 (14)
C5—C6—C7—O1	−179.21 (14)	O2—S1—C16—C17	165.84 (13)
C5—C6—C7—C2	0.5 (2)	C1—S1—C16—C17	−82.15 (14)
C8—O1—C7—C6	−179.40 (15)	C21—C16—C17—C18	−1.3 (3)
C8—O1—C7—C2	0.81 (16)	S1—C16—C17—C18	−178.73 (13)
C3—C2—C7—C6	−0.1 (2)	C16—C17—C18—C19	0.0 (3)
C1—C2—C7—C6	179.74 (14)	C17—C18—C19—F1	−179.83 (15)
C3—C2—C7—O1	179.70 (12)	C17—C18—C19—C20	0.4 (3)
C1—C2—C7—O1	−0.47 (16)	F1—C19—C20—C21	−179.32 (15)
C2—C1—C8—O1	0.56 (17)	C18—C19—C20—C21	0.5 (3)
S1—C1—C8—O1	177.47 (10)	C17—C16—C21—C20	2.1 (2)
C2—C1—C8—C15	−179.45 (15)	S1—C16—C21—C20	179.56 (12)
S1—C1—C8—C15	−2.5 (3)	C19—C20—C21—C16	−1.7 (2)
C7—O1—C8—C1	−0.84 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1ⁱ	0.95	2.48	3.283 (2)	142
C21—H21···O2ⁱⁱ	0.95	2.37	3.213 (2)	148
C10—H10B···Cg1ⁱⁱⁱ	0.99	2.86	3.624 (2)	135
C15—H15C···Cg1^iv	0.98	2.93	3.510 (2)	119

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁FO₂S
M_r	356.44
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.2531 (2), 10.1934 (2), 10.8151 (2)
α, β, γ (°)	81.127 (1), 66.716 (1), 72.248 (1)
V (Å³)	891.73 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.29 × 0.23 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.943, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	15790, 4073, 3436
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.04
No. of reflections	4073
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.27

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