2-(4-Fluoro­phen­yl)-5-iodo-7-methyl-3-phenyl­sulfinyl-1-benzo­furan

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

doi:10.1107/S1600536813011793

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o820

doi:10.1107/S1600536813011793

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2-(4-Fluorophenyl)-5-iodo-7-methyl-3-phenylsulfinyl-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 17 April 2013; accepted 30 April 2013; online 4 May 2013)

In the title compound, C₂₁H₁₄FIO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.007 (1) Å] of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 3.66 (7) and 82.37 (6)°, respectively. In the crystal, molecules are linked by pairs of C—H⋯I hydrogen bonds into centrosymmetric dimers, which are further packed into stacks along the b axis by C—H⋯O hydrogen bonds. In addition, the stacked molecules exhibit inversion-related S⋯O contacts [2.9627 (14) Å] involving the sulfinyl groups.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009 , 2012 ). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2008 ) and for a review of carbonyl–carbonyl interactions, see: Allen et al. (1998 ).

Experimental

Crystal data

C₂₁H₁₄FIO₂S
M_r = 476.28
Triclinic, $[P \overline 1]$
a = 8.1060 (3) Å
b = 10.7771 (4) Å
c = 11.2639 (4) Å
α = 71.814 (2)°
β = 74.496 (2)°
γ = 79.038 (2)°
V = 894.69 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.93 mm⁻¹
T = 173 K
0.36 × 0.28 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.562, T_max = 0.746
16292 measured reflections
4404 independent reflections
4125 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.062
S = 1.05
4404 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2ⁱ	0.95	2.36	3.314 (3)	177
C17—H17⋯I1ⁱⁱ	0.95	2.97	3.705 (2)	135
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z+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 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/S1600536813011793/ld2102sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813011793/ld2102Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813011793/ld2102Isup3.cml

checkCIF report

Comment top

As a part of our continuing study of 5-iodo-3-phenylsulfinyl-1-benzofuran derivatives containing phenyl (Choi et al., 2009) and 4-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 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 3.66 (7) and 82.37 (6)°, respectively. In the crystal structure (Fig. 2), molecules are linked by pairs of C—H···I hydrogen bonds into centrosymmetric dimers, which are further packed into stacks along the b 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) interpreted as similar to a type-II carbonyl–carbonyl interaction (Allen et al., 1998), with S1···O2ⁱⁱⁱ and O2..S1ⁱⁱⁱ distance of 2.9627 (14) Å .

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2009, 2012). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2008) and for a review of carbonyl–carbonyl interactions, see: Allen et al. (1998).

Experimental top

3-Chloroperoxybenzoic acid (77%, 179 mg, 0.8 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-7-methyl-3-phenylsulfanyl-1-benzofuran (322 mg, 0.7 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 473–474 K; R_f = 0.74 (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 benzene 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.
	Fig. 2. A view of the C—H..I, C—H···O and S···O interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x - 1, y, z; (ii) - x + 2, - y, - z + 2; (iii) - x + 2, - y, - z + 1; (iv) x + 1, y, z.]

2-(4-Fluorophenyl)-5-iodo-7-methyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₂₁H₁₄FIO₂S	Z = 2
M_r = 476.28	F(000) = 468
Triclinic, P1	D_x = 1.768 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1060 (3) Å	Cell parameters from 6652 reflections
b = 10.7771 (4) Å	θ = 2.6–28.4°
c = 11.2639 (4) Å	µ = 1.93 mm⁻¹
α = 71.814 (2)°	T = 173 K
β = 74.496 (2)°	Block, colourless
γ = 79.038 (2)°	0.36 × 0.28 × 0.19 mm
V = 894.69 (6) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	4404 independent reflections
Radiation source: rotating anode	4125 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.036
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.562, T_max = 0.746	l = −14→14
16292 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)] = 0.023	Hydrogen site location: difference Fourier map
wR(F²) = 0.062	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0291P)² + 0.4238P] where P = (F_o² + 2F_c²)/3
4404 reflections	(Δ/σ)_max = 0.002
236 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₂₁H₁₄FIO₂S	γ = 79.038 (2)°
M_r = 476.28	V = 894.69 (6) Å³
Triclinic, P1	Z = 2
a = 8.1060 (3) Å	Mo Kα radiation
b = 10.7771 (4) Å	µ = 1.93 mm⁻¹
c = 11.2639 (4) Å	T = 173 K
α = 71.814 (2)°	0.36 × 0.28 × 0.19 mm
β = 74.496 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4404 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4125 reflections with I > 2σ(I)
T_min = 0.562, T_max = 0.746	R_int = 0.036
16292 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.05	Δρ_max = 0.37 e Å⁻³
4404 reflections	Δρ_min = −0.63 e Å⁻³
236 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
I1	1.038283 (17)	0.207761 (13)	1.022854 (12)	0.03450 (6)
S1	0.88164 (6)	0.15272 (4)	0.52014 (4)	0.02267 (9)
F1	0.52793 (19)	0.62193 (14)	0.03604 (12)	0.0432 (3)
O1	0.76006 (17)	0.52135 (12)	0.54415 (12)	0.0240 (3)
O2	1.03200 (17)	0.08292 (13)	0.57680 (14)	0.0297 (3)
C1	0.8377 (2)	0.30667 (17)	0.55547 (17)	0.0219 (3)
C2	0.8726 (2)	0.32977 (17)	0.66597 (17)	0.0226 (3)
C3	0.9380 (2)	0.25313 (18)	0.77187 (18)	0.0256 (4)
H3	0.9754	0.1619	0.7836	0.031*
C4	0.9455 (2)	0.31737 (19)	0.85932 (18)	0.0263 (4)
C5	0.8945 (3)	0.45161 (19)	0.84379 (18)	0.0274 (4)
H5	0.9038	0.4903	0.9065	0.033*
C6	0.8304 (2)	0.52953 (18)	0.73849 (18)	0.0256 (4)
C7	0.8216 (2)	0.46343 (17)	0.65298 (17)	0.0232 (3)
C8	0.7708 (2)	0.42461 (17)	0.48521 (17)	0.0224 (3)
C9	0.7725 (3)	0.67397 (19)	0.7182 (2)	0.0336 (4)
H9A	0.7783	0.7163	0.6267	0.050*
H9B	0.8479	0.7132	0.7480	0.050*
H9C	0.6536	0.6868	0.7665	0.050*
C10	0.7072 (2)	0.47139 (17)	0.36758 (17)	0.0234 (3)
C11	0.7151 (3)	0.39187 (19)	0.28875 (19)	0.0285 (4)
H11	0.7626	0.3024	0.3120	0.034*
C12	0.6542 (3)	0.4420 (2)	0.17688 (19)	0.0313 (4)
H12	0.6595	0.3880	0.1233	0.038*
C13	0.5866 (3)	0.5714 (2)	0.14591 (18)	0.0305 (4)
C14	0.5757 (3)	0.6538 (2)	0.22019 (19)	0.0315 (4)
H14	0.5279	0.7431	0.1958	0.038*
C15	0.6363 (3)	0.60277 (19)	0.33112 (18)	0.0287 (4)
H15	0.6298	0.6580	0.3839	0.034*
C16	0.6935 (2)	0.08351 (17)	0.62724 (19)	0.0253 (4)
C17	0.7012 (3)	0.0107 (2)	0.7511 (2)	0.0351 (4)
H17	0.8053	−0.0028	0.7794	0.042*
C18	0.5561 (3)	−0.0422 (2)	0.8336 (3)	0.0457 (6)
H18	0.5598	−0.0921	0.9191	0.055*
C19	0.4053 (3)	−0.0223 (2)	0.7911 (3)	0.0484 (6)
H19	0.3053	−0.0579	0.8481	0.058*
C20	0.3990 (3)	0.0487 (3)	0.6670 (3)	0.0465 (6)
H20	0.2952	0.0611	0.6385	0.056*
C21	0.5442 (3)	0.1020 (2)	0.5834 (2)	0.0343 (4)
H21	0.5411	0.1505	0.4975	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.03624 (9)	0.04058 (9)	0.02868 (8)	−0.00585 (6)	−0.01368 (6)	−0.00611 (6)
S1	0.0228 (2)	0.01980 (19)	0.0283 (2)	0.00242 (16)	−0.00949 (17)	−0.01045 (16)
F1	0.0501 (8)	0.0477 (7)	0.0309 (6)	−0.0013 (6)	−0.0206 (6)	−0.0025 (5)
O1	0.0290 (7)	0.0186 (6)	0.0250 (6)	−0.0013 (5)	−0.0063 (5)	−0.0078 (5)
O2	0.0234 (6)	0.0282 (7)	0.0422 (8)	0.0057 (5)	−0.0148 (6)	−0.0153 (6)
C1	0.0216 (8)	0.0206 (8)	0.0248 (8)	−0.0013 (6)	−0.0050 (7)	−0.0091 (6)
C2	0.0213 (8)	0.0227 (8)	0.0259 (8)	−0.0038 (6)	−0.0048 (7)	−0.0092 (7)
C3	0.0254 (9)	0.0249 (8)	0.0288 (9)	−0.0039 (7)	−0.0085 (7)	−0.0077 (7)
C4	0.0248 (9)	0.0311 (9)	0.0241 (9)	−0.0067 (7)	−0.0074 (7)	−0.0056 (7)
C5	0.0277 (9)	0.0314 (9)	0.0269 (9)	−0.0091 (8)	−0.0030 (7)	−0.0126 (7)
C6	0.0275 (9)	0.0243 (8)	0.0264 (9)	−0.0079 (7)	−0.0016 (7)	−0.0098 (7)
C7	0.0235 (8)	0.0226 (8)	0.0237 (8)	−0.0042 (7)	−0.0031 (7)	−0.0076 (7)
C8	0.0218 (8)	0.0217 (8)	0.0246 (8)	−0.0024 (6)	−0.0025 (7)	−0.0099 (7)
C9	0.0434 (12)	0.0249 (9)	0.0352 (10)	−0.0051 (8)	−0.0064 (9)	−0.0135 (8)
C10	0.0221 (8)	0.0227 (8)	0.0237 (8)	−0.0007 (7)	−0.0031 (7)	−0.0067 (7)
C11	0.0322 (10)	0.0255 (9)	0.0281 (9)	0.0015 (7)	−0.0095 (8)	−0.0083 (7)
C12	0.0342 (10)	0.0354 (10)	0.0260 (9)	−0.0029 (8)	−0.0076 (8)	−0.0110 (8)
C13	0.0279 (9)	0.0365 (10)	0.0236 (9)	−0.0027 (8)	−0.0078 (8)	−0.0022 (8)
C14	0.0312 (10)	0.0271 (9)	0.0303 (10)	0.0030 (8)	−0.0073 (8)	−0.0031 (8)
C15	0.0312 (10)	0.0255 (9)	0.0273 (9)	0.0001 (7)	−0.0050 (8)	−0.0076 (7)
C16	0.0244 (9)	0.0195 (8)	0.0358 (10)	0.0003 (7)	−0.0100 (8)	−0.0121 (7)
C17	0.0366 (11)	0.0256 (9)	0.0420 (12)	−0.0042 (8)	−0.0141 (9)	−0.0031 (8)
C18	0.0474 (14)	0.0339 (11)	0.0486 (14)	−0.0100 (10)	−0.0034 (11)	−0.0043 (10)
C19	0.0365 (12)	0.0406 (13)	0.0661 (17)	−0.0133 (10)	0.0050 (12)	−0.0207 (12)
C20	0.0274 (11)	0.0477 (13)	0.0755 (18)	−0.0037 (9)	−0.0134 (11)	−0.0312 (13)
C21	0.0285 (10)	0.0350 (10)	0.0471 (12)	0.0010 (8)	−0.0162 (9)	−0.0186 (9)

Geometric parameters (Å, º) top

I1—C4	2.0974 (19)	C9—H9C	0.9800
S1—O2ⁱ	2.9627 (14)	C10—C11	1.397 (3)
S1—O2	1.4920 (14)	C10—C15	1.399 (3)
S1—C1	1.7748 (17)	C11—C12	1.389 (3)
S1—C16	1.796 (2)	C11—H11	0.9500
F1—C13	1.360 (2)	C12—C13	1.369 (3)
O1—C7	1.368 (2)	C12—H12	0.9500
O1—C8	1.379 (2)	C13—C14	1.375 (3)
C1—C8	1.369 (2)	C14—C15	1.379 (3)
C1—C2	1.449 (2)	C14—H14	0.9500
C2—C7	1.393 (2)	C15—H15	0.9500
C2—C3	1.394 (3)	C16—C17	1.382 (3)
C3—C4	1.388 (3)	C16—C21	1.383 (3)
C3—H3	0.9500	C17—C18	1.383 (3)
C4—C5	1.396 (3)	C17—H17	0.9500
C5—C6	1.387 (3)	C18—C19	1.385 (4)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.387 (2)	C19—C20	1.378 (4)
C6—C9	1.501 (3)	C19—H19	0.9500
C8—C10	1.458 (3)	C20—C21	1.390 (3)
C9—H9A	0.9800	C20—H20	0.9500
C9—H9B	0.9800	C21—H21	0.9500

O2—S1—C1	105.04 (8)	C11—C10—C15	118.34 (17)
O2—S1—C16	106.95 (9)	C11—C10—C8	123.24 (16)
C1—S1—C16	97.02 (8)	C15—C10—C8	118.41 (16)
O2—S1—O2ⁱ	78.36 (6)	C12—C11—C10	120.83 (18)
C1—S1—O2ⁱ	172.01 (7)	C12—C11—H11	119.6
C16—S1—O2ⁱ	88.76 (6)	C10—C11—H11	119.6
C7—O1—C8	107.21 (13)	C13—C12—C11	118.25 (19)
C8—C1—C2	107.21 (15)	C13—C12—H12	120.9
C8—C1—S1	127.99 (14)	C11—C12—H12	120.9
C2—C1—S1	124.78 (13)	F1—C13—C12	118.80 (19)
C7—C2—C3	119.35 (17)	F1—C13—C14	117.99 (18)
C7—C2—C1	104.84 (16)	C12—C13—C14	123.21 (19)
C3—C2—C1	135.81 (17)	C13—C14—C15	117.99 (18)
C4—C3—C2	116.34 (17)	C13—C14—H14	121.0
C4—C3—H3	121.8	C15—C14—H14	121.0
C2—C3—H3	121.8	C14—C15—C10	121.38 (18)
C3—C4—C5	123.24 (18)	C14—C15—H15	119.3
C3—C4—I1	118.53 (14)	C10—C15—H15	119.3
C5—C4—I1	118.23 (14)	C17—C16—C21	121.16 (19)
C6—C5—C4	121.18 (17)	C17—C16—S1	119.54 (15)
C6—C5—H5	119.4	C21—C16—S1	119.29 (16)
C4—C5—H5	119.4	C16—C17—C18	119.5 (2)
C5—C6—C7	114.83 (17)	C16—C17—H17	120.3
C5—C6—C9	123.14 (17)	C18—C17—H17	120.3
C7—C6—C9	122.02 (18)	C17—C18—C19	119.7 (2)
O1—C7—C6	124.22 (16)	C17—C18—H18	120.1
O1—C7—C2	110.72 (15)	C19—C18—H18	120.1
C6—C7—C2	125.06 (18)	C20—C19—C18	120.6 (2)
C1—C8—O1	110.02 (16)	C20—C19—H19	119.7
C1—C8—C10	136.31 (16)	C18—C19—H19	119.7
O1—C8—C10	113.67 (15)	C19—C20—C21	120.1 (2)
C6—C9—H9A	109.5	C19—C20—H20	120.0
C6—C9—H9B	109.5	C21—C20—H20	120.0
H9A—C9—H9B	109.5	C16—C21—C20	119.0 (2)
C6—C9—H9C	109.5	C16—C21—H21	120.5
H9A—C9—H9C	109.5	C20—C21—H21	120.5
H9B—C9—H9C	109.5

O2—S1—C1—C8	149.12 (17)	S1—C1—C8—C10	2.6 (3)
C16—S1—C1—C8	−101.17 (18)	C7—O1—C8—C1	0.17 (19)
O2—S1—C1—C2	−28.97 (18)	C7—O1—C8—C10	179.24 (15)
C16—S1—C1—C2	80.74 (17)	C1—C8—C10—C11	−5.0 (3)
C8—C1—C2—C7	0.3 (2)	O1—C8—C10—C11	176.23 (17)
S1—C1—C2—C7	178.71 (13)	C1—C8—C10—C15	175.6 (2)
C8—C1—C2—C3	179.5 (2)	O1—C8—C10—C15	−3.1 (2)
S1—C1—C2—C3	−2.1 (3)	C15—C10—C11—C12	0.1 (3)
C7—C2—C3—C4	0.8 (3)	C8—C10—C11—C12	−179.26 (18)
C1—C2—C3—C4	−178.3 (2)	C10—C11—C12—C13	0.1 (3)
C2—C3—C4—C5	−1.2 (3)	C11—C12—C13—F1	179.46 (18)
C2—C3—C4—I1	178.91 (13)	C11—C12—C13—C14	−0.1 (3)
C3—C4—C5—C6	0.7 (3)	F1—C13—C14—C15	−179.55 (18)
I1—C4—C5—C6	−179.40 (14)	C12—C13—C14—C15	0.0 (3)
C4—C5—C6—C7	0.2 (3)	C13—C14—C15—C10	0.1 (3)
C4—C5—C6—C9	179.44 (18)	C11—C10—C15—C14	−0.2 (3)
C8—O1—C7—C6	−179.63 (17)	C8—C10—C15—C14	179.19 (18)
C8—O1—C7—C2	0.02 (19)	O2—S1—C16—C17	16.79 (18)
C5—C6—C7—O1	178.99 (16)	C1—S1—C16—C17	−91.31 (16)
C9—C6—C7—O1	−0.2 (3)	O2—S1—C16—C21	−162.03 (15)
C5—C6—C7—C2	−0.6 (3)	C1—S1—C16—C21	89.87 (16)
C9—C6—C7—C2	−179.84 (18)	C21—C16—C17—C18	−1.4 (3)
C3—C2—C7—O1	−179.54 (16)	S1—C16—C17—C18	179.85 (17)
C1—C2—C7—O1	−0.2 (2)	C16—C17—C18—C19	0.3 (3)
C3—C2—C7—C6	0.1 (3)	C17—C18—C19—C20	0.7 (4)
C1—C2—C7—C6	179.46 (17)	C18—C19—C20—C21	−0.6 (4)
C2—C1—C8—O1	−0.3 (2)	C17—C16—C21—C20	1.5 (3)
S1—C1—C8—O1	−178.64 (13)	S1—C16—C21—C20	−179.72 (16)
C2—C1—C8—C10	−179.0 (2)	C19—C20—C21—C16	−0.5 (3)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2ⁱⁱ	0.95	2.36	3.314 (3)	177
C17—H17···I1ⁱⁱⁱ	0.95	2.97	3.705 (2)	135

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄FIO₂S
M_r	476.28
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.1060 (3), 10.7771 (4), 11.2639 (4)
α, β, γ (°)	71.814 (2), 74.496 (2), 79.038 (2)
V (Å³)	894.69 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.93
Crystal size (mm)	0.36 × 0.28 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.562, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	16292, 4404, 4125
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.062, 1.05
No. of reflections	4404
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.63

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
C20—H20···O2ⁱ	0.95	2.36	3.314 (3)	177.0
C17—H17···I1ⁱⁱ	0.95	2.97	3.705 (2)	135.2

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

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

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