5-Cyclo­hexyl-2-(2-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536813012701

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o887

doi:10.1107/S1600536813012701

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5-Cyclohexyl-2-(2-fluorophenyl)-3-methylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a 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 7 May 2013; accepted 9 May 2013; online 15 May 2013)

In the title compound, C₂₁H₂₁FO₂S, the cyclohexyl ring adopts a chair conformation. The 2-fluorobenzene ring makes a dihedral angle of 38.68 (6)° with the mean plane [r.m.s. deviation = 0.018 (2) Å] of the benzofuran fragment. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds into dimers, which are further packed into stacks along the c axis by C—H⋯O hydrogen bonds. In addition, the stacked molecules exhibit S⋯O contacts [3.1733 (13) Å] involving the sulfinyl groups. The F atom is disordered over two positions, with site-occupancy factors of 0.961 (3) and 0.039 (3).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 , 2012 ). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2008 ). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998 ).

Experimental

Crystal data

C₂₁H₂₁FO₂S
M_r = 356.44
Monoclinic, C 2/c
a = 33.0231 (12) Å
b = 5.6347 (2) Å
c = 19.2200 (6) Å
β = 95.855 (2)°
V = 3557.7 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.31 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.545, T_max = 0.746
29435 measured reflections
4455 independent reflections
3455 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.122
S = 1.07
4455 reflections
237 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2ⁱ	0.95	2.44	3.220 (2)	140
C21—H21A⋯O2ⁱⁱ	0.98	2.57	3.265 (2)	128
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813012701/tk5225sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012701/tk5225Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012701/tk5225Isup3.cml

checkCIF report

Comment top

As a part of our continuing study of 5-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives containing 4-fluorophenyl (Choi et al., 2011) and 3-fluorophenyl (Choi et al., 2012) substituents in 2-position, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.018 (2) Å from the least-squares plane defined by the nine constituent atoms. In the 2-fluorobenzene ring, the F atom is disordered over two positions with site-occupancy factors, from refinement, of 0.961 (3) (part A) and 0.039 (3) (part B). The cyclohexyl ring has the chair form. The dihedral angle formed by the 2-fluorobenzene ring and the mean plane of the benzofuran fragment is 38.68 (6)°. In the crystal structure (Fig. 2), molecules are linked by pairs of C—H···O hydrogen bonds into centrosymmetric dimers, which are further packed into stacks along the c axis by C—H···O hydrogen bonds (Table 1). In addition, the crystal packing (Fig. 2) exhibits a sulfinyl–sulfinyl interaction (Choi et al., 2008) similar to a type-II carbonyl-carbonyl interaction (Allen et al., 1998), with a S1···O2ⁱⁱ distance of 3.1733 (13) Å (symmetry operation ii: 1/2-x, 1/2-y, 1-z).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2011, 2012). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2008). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998).

Experimental top

3-Chloroperoxybenzoic acid (77%, 208 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-(2-fluorophenyl)-3-methylsulfanyl-1-benzofuran (271 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5 h, 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 78%, M.pt: 452–453 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 for Windows (Farrugia, 2012) 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 F atom of the 2-fluorophenyl ring is disordered over two positions with site occupancy factors, from refinement of 0.961 (3) (part A) and 0.039 (3) (part B).
	Fig. 2. A view of the C—H···O and S···O interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding and disordered part B atoms were omitted for clarity. [Symmetry codes: (i) xX, - y + 1, z - 1/2; (ii) - x + 1/2, - y + 1/2, - z + 1; (iii) x, - y + 1, z + 1/2 .]

5-Cyclohexyl-2-(2-fluorophenyl)-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₂₁H₂₁FO₂S	F(000) = 1504
M_r = 356.44	D_x = 1.331 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7608 reflections
a = 33.0231 (12) Å	θ = 2.4–27.9°
b = 5.6347 (2) Å	µ = 0.20 mm⁻¹
c = 19.2200 (6) Å	T = 173 K
β = 95.855 (2)°	Block, colourless
V = 3557.7 (2) Å³	0.31 × 0.15 × 0.09 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD diffractometer	4455 independent reflections
Radiation source: rotating anode	3455 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.066
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.1°
ϕ and ω scans	h = −44→42
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −5→7
T_min = 0.545, T_max = 0.746	l = −25→25
29435 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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F²) = 0.122	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0503P)² + 2.7846P] where P = (F_o² + 2F_c²)/3
4455 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.36 e Å⁻³
14 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₁H₂₁FO₂S	V = 3557.7 (2) Å³
M_r = 356.44	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.0231 (12) Å	µ = 0.20 mm⁻¹
b = 5.6347 (2) Å	T = 173 K
c = 19.2200 (6) Å	0.31 × 0.15 × 0.09 mm
β = 95.855 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4455 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3455 reflections with I > 2σ(I)
T_min = 0.545, T_max = 0.746	R_int = 0.066
29435 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	14 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.07	Δρ_max = 0.36 e Å⁻³
4455 reflections	Δρ_min = −0.33 e Å⁻³
237 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	Occ. (<1)
S1	0.206366 (12)	0.27237 (7)	0.42614 (2)	0.02355 (12)
O1	0.11688 (4)	0.5340 (3)	0.29615 (6)	0.0347 (3)
O2	0.21653 (4)	0.4453 (2)	0.48408 (6)	0.0320 (3)
C1	0.16017 (5)	0.3784 (3)	0.38215 (8)	0.0233 (3)
C2	0.12801 (5)	0.4947 (3)	0.41447 (9)	0.0251 (4)
C3	0.11880 (5)	0.5338 (3)	0.48284 (9)	0.0271 (4)
H3	0.1356	0.4687	0.5212	0.033*
C4	0.08520 (6)	0.6673 (4)	0.49437 (9)	0.0340 (4)
C5	0.06078 (7)	0.7595 (4)	0.43703 (11)	0.0494 (6)
H5	0.0377	0.8519	0.4454	0.059*
C6	0.06884 (7)	0.7218 (4)	0.36850 (11)	0.0497 (6)
H6	0.0519	0.7849	0.3300	0.060*
C7	0.10277 (5)	0.5879 (4)	0.35935 (9)	0.0330 (4)
C8	0.15236 (5)	0.4084 (3)	0.31233 (8)	0.0252 (4)
C9	0.07601 (6)	0.7166 (4)	0.56872 (10)	0.0358 (4)
H9	0.0931	0.6047	0.5996	0.043*
C10	0.03215 (7)	0.6704 (5)	0.58103 (12)	0.0508 (6)
H10A	0.0251	0.5041	0.5685	0.061*
H10B	0.0141	0.7755	0.5504	0.061*
C11	0.02494 (8)	0.7145 (5)	0.65731 (13)	0.0620 (8)
H11A	−0.0042	0.6906	0.6631	0.074*
H11B	0.0409	0.5990	0.6877	0.074*
C12	0.03733 (7)	0.9641 (5)	0.67931 (12)	0.0505 (6)
H12A	0.0194	1.0792	0.6522	0.061*
H12B	0.0338	0.9858	0.7295	0.061*
C13	0.08082 (7)	1.0129 (5)	0.66758 (11)	0.0504 (6)
H13A	0.0990	0.9109	0.6990	0.061*
H13B	0.0874	1.1804	0.6794	0.061*
C14	0.08855 (7)	0.9658 (4)	0.59173 (11)	0.0465 (5)
H14A	0.0731	1.0822	0.5609	0.056*
H14B	0.1179	0.9881	0.5868	0.056*
C15	0.17462 (5)	0.3439 (3)	0.25303 (8)	0.0263 (4)
C16A	0.19517 (6)	0.1306 (3)	0.25044 (9)	0.0301 (4)	0.961 (3)
F1A	0.19125 (4)	−0.0328 (2)	0.30066 (6)	0.0405 (4)	0.961 (3)
C16B	0.19517 (6)	0.1306 (3)	0.25044 (9)	0.0301 (4)	0.04
H16B	0.1930	0.0181	0.2867	0.036*	0.039 (3)
C17	0.21859 (6)	0.0748 (4)	0.19744 (10)	0.0370 (5)
H17	0.2329	−0.0714	0.1979	0.044*
C18	0.22086 (6)	0.2346 (4)	0.14361 (10)	0.0383 (5)
H18	0.2371	0.1992	0.1068	0.046*
C19	0.19974 (6)	0.4449 (4)	0.14305 (9)	0.0374 (5)
H19	0.2010	0.5530	0.1054	0.045*
C20A	0.17669 (6)	0.4997 (4)	0.19703 (9)	0.0317 (4)	0.961 (3)
H20A	0.1621	0.6452	0.1960	0.038*	0.961 (3)
C20B	0.17669 (6)	0.4997 (4)	0.19703 (9)	0.0317 (4)	0.04
F1B	0.1515 (6)	0.680 (3)	0.1832 (13)	0.031 (7)	0.039 (3)
C21	0.18645 (6)	0.0135 (3)	0.46404 (10)	0.0360 (4)
H21A	0.2084	−0.0696	0.4923	0.054*
H21B	0.1746	−0.0918	0.4268	0.054*
H21C	0.1654	0.0599	0.4938	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0256 (2)	0.0259 (2)	0.0196 (2)	0.00267 (16)	0.00441 (15)	0.00009 (16)
O1	0.0323 (7)	0.0526 (8)	0.0196 (6)	0.0133 (6)	0.0049 (5)	0.0022 (6)
O2	0.0346 (7)	0.0348 (7)	0.0257 (6)	0.0027 (5)	−0.0020 (5)	−0.0065 (5)
C1	0.0271 (8)	0.0246 (8)	0.0186 (8)	0.0012 (7)	0.0045 (6)	−0.0007 (6)
C2	0.0257 (8)	0.0292 (9)	0.0209 (8)	0.0016 (7)	0.0054 (6)	0.0005 (7)
C3	0.0263 (8)	0.0339 (9)	0.0215 (8)	0.0018 (7)	0.0046 (7)	0.0008 (7)
C4	0.0352 (10)	0.0427 (11)	0.0254 (9)	0.0066 (8)	0.0096 (8)	−0.0003 (8)
C5	0.0427 (12)	0.0707 (16)	0.0366 (11)	0.0285 (11)	0.0126 (9)	0.0036 (11)
C6	0.0448 (12)	0.0762 (16)	0.0283 (10)	0.0309 (11)	0.0047 (9)	0.0060 (10)
C7	0.0325 (10)	0.0469 (11)	0.0203 (9)	0.0098 (8)	0.0063 (7)	0.0005 (8)
C8	0.0259 (8)	0.0285 (9)	0.0214 (8)	0.0027 (7)	0.0033 (6)	−0.0007 (7)
C9	0.0378 (10)	0.0461 (11)	0.0253 (9)	0.0097 (9)	0.0110 (8)	−0.0015 (8)
C10	0.0497 (13)	0.0640 (15)	0.0423 (12)	−0.0144 (11)	0.0225 (10)	−0.0213 (11)
C11	0.0598 (15)	0.0855 (19)	0.0462 (13)	−0.0247 (14)	0.0324 (12)	−0.0241 (13)
C12	0.0426 (12)	0.0723 (16)	0.0386 (12)	0.0047 (11)	0.0134 (10)	−0.0210 (11)
C13	0.0461 (12)	0.0668 (16)	0.0399 (12)	−0.0060 (11)	0.0113 (10)	−0.0195 (11)
C14	0.0444 (12)	0.0585 (14)	0.0390 (12)	−0.0084 (10)	0.0163 (9)	−0.0109 (10)
C15	0.0283 (9)	0.0329 (9)	0.0180 (8)	−0.0016 (7)	0.0037 (6)	−0.0032 (7)
C16A	0.0364 (10)	0.0315 (10)	0.0227 (9)	−0.0017 (8)	0.0044 (7)	−0.0041 (7)
F1A	0.0590 (8)	0.0315 (6)	0.0326 (7)	0.0058 (5)	0.0117 (5)	0.0008 (5)
C16B	0.0364 (10)	0.0315 (10)	0.0227 (9)	−0.0017 (8)	0.0044 (7)	−0.0041 (7)
C17	0.0361 (10)	0.0422 (11)	0.0336 (10)	0.0015 (8)	0.0071 (8)	−0.0124 (9)
C18	0.0362 (10)	0.0545 (13)	0.0255 (9)	−0.0047 (9)	0.0096 (8)	−0.0142 (9)
C19	0.0396 (11)	0.0545 (13)	0.0187 (9)	−0.0068 (9)	0.0059 (8)	0.0012 (8)
C20A	0.0335 (10)	0.0391 (11)	0.0223 (9)	0.0002 (8)	0.0025 (7)	0.0007 (8)
C20B	0.0335 (10)	0.0391 (11)	0.0223 (9)	0.0002 (8)	0.0025 (7)	0.0007 (8)
F1B	0.030 (10)	0.036 (11)	0.028 (10)	−0.002 (8)	0.006 (7)	0.000 (8)
C21	0.0427 (11)	0.0311 (10)	0.0350 (10)	0.0002 (8)	0.0070 (9)	0.0103 (8)

Geometric parameters (Å, º) top

S1—O2	1.4921 (13)	C11—C12	1.513 (3)
S1—C1	1.7708 (17)	C11—H11A	0.9900
S1—C21	1.7856 (19)	C11—H11B	0.9900
S1—O2ⁱ	3.1733 (13)	C12—C13	1.502 (3)
O1—C8	1.377 (2)	C12—H12A	0.9900
O1—C7	1.379 (2)	C12—H12B	0.9900
C1—C8	1.351 (2)	C13—C14	1.529 (3)
C1—C2	1.442 (2)	C13—H13A	0.9900
C2—C7	1.383 (2)	C13—H13B	0.9900
C2—C3	1.396 (2)	C14—H14A	0.9900
C3—C4	1.377 (2)	C14—H14B	0.9900
C3—H3	0.9500	C15—C16A	1.384 (3)
C4—C5	1.398 (3)	C15—C20A	1.396 (2)
C4—C9	1.516 (2)	C16A—F1A	1.3495 (19)
C5—C6	1.387 (3)	C16A—C17	1.377 (2)
C5—H5	0.9500	C17—C18	1.380 (3)
C6—C7	1.377 (3)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.374 (3)
C8—C15	1.464 (2)	C18—H18	0.9500
C9—C10	1.514 (3)	C19—C20A	1.383 (3)
C9—C14	1.517 (3)	C19—H19	0.9500
C9—H9	1.0000	C20A—H20A	0.9500
C10—C11	1.529 (3)	C21—H21A	0.9800
C10—H10A	0.9900	C21—H21B	0.9800
C10—H10B	0.9900	C21—H21C	0.9800

O2—S1—C1	104.66 (7)	C12—C11—H11B	109.5
O2—S1—C21	107.05 (9)	C10—C11—H11B	109.5
C1—S1—C21	97.77 (9)	H11A—C11—H11B	108.1
O2—S1—O2ⁱ	74.92 (6)	C13—C12—C11	111.33 (19)
C1—S1—O2ⁱ	173.96 (6)	C13—C12—H12A	109.4
C21—S1—O2ⁱ	76.76 (7)	C11—C12—H12A	109.4
C8—O1—C7	105.70 (13)	C13—C12—H12B	109.4
C8—C1—C2	107.27 (15)	C11—C12—H12B	109.4
C8—C1—S1	125.75 (13)	H12A—C12—H12B	108.0
C2—C1—S1	125.75 (12)	C12—C13—C14	111.50 (18)
C7—C2—C3	119.27 (15)	C12—C13—H13A	109.3
C7—C2—C1	104.79 (14)	C14—C13—H13A	109.3
C3—C2—C1	135.90 (16)	C12—C13—H13B	109.3
C4—C3—C2	119.62 (16)	C14—C13—H13B	109.3
C4—C3—H3	120.2	H13A—C13—H13B	108.0
C2—C3—H3	120.2	C9—C14—C13	111.81 (19)
C3—C4—C5	119.06 (17)	C9—C14—H14A	109.3
C3—C4—C9	119.58 (17)	C13—C14—H14A	109.3
C5—C4—C9	121.34 (17)	C9—C14—H14B	109.3
C6—C5—C4	122.73 (18)	C13—C14—H14B	109.3
C6—C5—H5	118.6	H14A—C14—H14B	107.9
C4—C5—H5	118.6	C16A—C15—C20A	117.12 (15)
C7—C6—C5	116.29 (19)	C16A—C15—C8	122.04 (16)
C7—C6—H6	121.9	C20A—C15—C8	120.82 (16)
C5—C6—H6	121.9	F1A—C16A—C17	118.39 (17)
C6—C7—O1	125.86 (17)	F1A—C16A—C15	118.93 (15)
C6—C7—C2	123.02 (17)	C17—C16A—C15	122.65 (17)
O1—C7—C2	111.09 (15)	C16A—C17—C18	118.91 (19)
C1—C8—O1	111.12 (14)	C16A—C17—H17	120.5
C1—C8—C15	133.03 (16)	C18—C17—H17	120.5
O1—C8—C15	115.78 (14)	C19—C18—C17	120.16 (17)
C10—C9—C4	113.72 (17)	C19—C18—H18	119.9
C10—C9—C14	110.52 (17)	C17—C18—H18	119.9
C4—C9—C14	111.67 (17)	C18—C19—C20A	120.30 (18)
C10—C9—H9	106.8	C18—C19—H19	119.8
C4—C9—H9	106.8	C20A—C19—H19	119.8
C14—C9—H9	106.8	C19—C20A—C15	120.78 (18)
C9—C10—C11	111.53 (18)	C19—C20A—H20A	119.6
C9—C10—H10A	109.3	C15—C20A—H20A	119.6
C11—C10—H10A	109.3	S1—C21—H21A	109.5
C9—C10—H10B	109.3	S1—C21—H21B	109.5
C11—C10—H10B	109.3	H21A—C21—H21B	109.5
H10A—C10—H10B	108.0	S1—C21—H21C	109.5
C12—C11—C10	110.8 (2)	H21A—C21—H21C	109.5
C12—C11—H11A	109.5	H21B—C21—H21C	109.5
C10—C11—H11A	109.5

O2—S1—C1—C8	131.23 (16)	C7—O1—C8—C15	−176.16 (16)
C21—S1—C1—C8	−118.80 (17)	C3—C4—C9—C10	−132.0 (2)
O2—S1—C1—C2	−34.53 (17)	C5—C4—C9—C10	49.6 (3)
C21—S1—C1—C2	75.45 (16)	C3—C4—C9—C14	102.1 (2)
C8—C1—C2—C7	−0.1 (2)	C5—C4—C9—C14	−76.3 (3)
S1—C1—C2—C7	167.87 (14)	C4—C9—C10—C11	178.0 (2)
C8—C1—C2—C3	−178.0 (2)	C14—C9—C10—C11	−55.5 (3)
S1—C1—C2—C3	−10.0 (3)	C9—C10—C11—C12	56.3 (3)
C7—C2—C3—C4	−1.0 (3)	C10—C11—C12—C13	−55.9 (3)
C1—C2—C3—C4	176.7 (2)	C11—C12—C13—C14	55.2 (3)
C2—C3—C4—C5	0.5 (3)	C10—C9—C14—C13	54.5 (3)
C2—C3—C4—C9	−177.98 (17)	C4—C9—C14—C13	−177.83 (17)
C3—C4—C5—C6	0.2 (4)	C12—C13—C14—C9	−54.7 (3)
C9—C4—C5—C6	178.6 (2)	C1—C8—C15—C16A	39.3 (3)
C4—C5—C6—C7	−0.3 (4)	O1—C8—C15—C16A	−143.89 (17)
C5—C6—C7—O1	−178.3 (2)	C1—C8—C15—C20A	−139.2 (2)
C5—C6—C7—C2	−0.2 (4)	O1—C8—C15—C20A	37.6 (2)
C8—O1—C7—C6	176.9 (2)	C20A—C15—C16A—F1A	−174.72 (16)
C8—O1—C7—C2	−1.4 (2)	C8—C15—C16A—F1A	6.7 (3)
C3—C2—C7—C6	0.9 (3)	C20A—C15—C16A—C17	3.3 (3)
C1—C2—C7—C6	−177.5 (2)	C8—C15—C16A—C17	−175.27 (17)
C3—C2—C7—O1	179.23 (16)	F1A—C16A—C17—C18	176.19 (17)
C1—C2—C7—O1	0.9 (2)	C15—C16A—C17—C18	−1.9 (3)
C2—C1—C8—O1	−0.8 (2)	C16A—C17—C18—C19	−0.5 (3)
S1—C1—C8—O1	−168.73 (13)	C17—C18—C19—C20A	1.2 (3)
C2—C1—C8—C15	176.11 (19)	C18—C19—C20A—C15	0.4 (3)
S1—C1—C8—C15	8.2 (3)	C16A—C15—C20A—C19	−2.5 (3)
C7—O1—C8—C1	1.3 (2)	C8—C15—C20A—C19	176.08 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2ⁱⁱ	0.95	2.44	3.220 (2)	140
C21—H21A···O2ⁱ	0.98	2.57	3.265 (2)	128

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁FO₂S
M_r	356.44
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	33.0231 (12), 5.6347 (2), 19.2200 (6)
β (°)	95.855 (2)
V (Å³)	3557.7 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.31 × 0.15 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.545, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	29435, 4455, 3455
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.122, 1.07
No. of reflections	4455
No. of parameters	237
No. of restraints	14
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.33

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2ⁱ	0.95	2.44	3.220 (2)	140
C21—H21A···O2ⁱⁱ	0.98	2.57	3.265 (2)	128

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

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329. Web of Science CrossRef CAS IUCr Journals 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. & Lee, U. (2012). Acta Cryst. E68, o944. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o1061. 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. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar