2-(4-Fluoro­phen­yl)-5-iodo-3-methyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536809051642

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o44

doi:10.1107/S1600536809051642

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2-(4-Fluorophenyl)-5-iodo-3-methylsulfinyl-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 30 November 2009; accepted 1 December 2009; online 4 December 2009)

In the title compound, C₁₅H₁₀FIO₂S, the O atom and the methyl group of the methylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment. The 4-fluorophenyl ring is rotated out of the benzofuran plane by a dihedral angle of 28.33 (5)°. The crystal structure is stabilized by a weak non-classical intermolecular C—H⋯O hydrogen bond and an I⋯O halogen interaction [3.211 (1) Å].

Related literature

For the crystal structures of similar 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a ,b ). For natural products with benzofuran ring systems, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₀FIO₂S
M_r = 400.19
Triclinic, $[P \overline 1]$
a = 8.1045 (2) Å
b = 8.2699 (2) Å
c = 11.0999 (3) Å
α = 94.538 (1)°
β = 91.118 (1)°
γ = 111.982 (1)°
V = 686.73 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.49 mm⁻¹
T = 173 K
0.32 × 0.31 × 0.30 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.504, T_max = 0.526
12180 measured reflections
3179 independent reflections
3130 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.047
S = 1.17
3179 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.90 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.95	2.53	3.432 (2)	158
Symmetry code: (i) -x+1, -y+1, -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 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536809051642/zq2022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051642/zq2022Isup2.hkl

checkCIF report

Comment top

Molecules involving benzofuran moiety have attracted widespread interest owing to their presence in natural products (Akgul & Anil, 2003; Soekamto et al., 2003) and their biological activity (Aslam et al., 2006; Galal et al., 2009). As a part of our continuing studies of the effect of side chain substituents on the solid state structures of 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran analogues (Choi et al., 2009a,b), we report the crystal structure of 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 dihedral angle formed by the plane of the benzofuran and the 4-fluorophenyl ring is 28.33 (5)°. The crystal packing (Fig. 2) is stabilized by a weak non-classical intermolecular C—H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the S═O unit, with a C10—H10···O2ⁱ (Table 1), and an I···O halogen bond between the iodine and the oxygen of the S═O unit [I···O2ⁱⁱ = 3.211 (1) Å; C—I···Oⁱⁱ = 170.98 (5)°] (Politzer et al., 2007).

Related literature top

For the crystal structures of similar 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a,b). For natural products with benzofuran ring systems, see: Akgul & Anil (2003); Soekamto et al. (2003). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-Chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-3-methylsulfanyl-1-benzofuran (384 mg, 1.0 mmol) in dichloromethane (20 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 87%, m.p. 485–486 K; R_f = 0.66 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in chloroforrm 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. C—H···O and C—I···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y + 1, - z + 1; (ii) - x + 1, - y + 1, - z; (iii) x, y, z + 1.]

2-(4-Fluorophenyl)-5-iodo-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₁₅H₁₀FIO₂S	Z = 2
M_r = 400.19	F(000) = 388
Triclinic, P1	D_x = 1.935 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1045 (2) Å	Cell parameters from 9982 reflections
b = 8.2699 (2) Å	θ = 2.7–27.7°
c = 11.0999 (3) Å	µ = 2.49 mm⁻¹
α = 94.538 (1)°	T = 173 K
β = 91.118 (1)°	Block, colourless
γ = 111.982 (1)°	0.32 × 0.31 × 0.30 mm
V = 686.73 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3179 independent reflections
Radiation source: Rotating Anode	3130 reflections with I > 2σ(I)
HELIOS monochromator	R_int = 0.024
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.7°, θ_min = 1.8°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.504, T_max = 0.526	l = −13→14
12180 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)] = 0.018	Hydrogen site location: difference Fourier map
wR(F²) = 0.047	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0241P)² + 0.2941P] where P = (F_o² + 2F_c²)/3
3179 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.90 e Å⁻³

Crystal data top

C₁₅H₁₀FIO₂S	γ = 111.982 (1)°
M_r = 400.19	V = 686.73 (3) Å³
Triclinic, P1	Z = 2
a = 8.1045 (2) Å	Mo Kα radiation
b = 8.2699 (2) Å	µ = 2.49 mm⁻¹
c = 11.0999 (3) Å	T = 173 K
α = 94.538 (1)°	0.32 × 0.31 × 0.30 mm
β = 91.118 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3179 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3130 reflections with I > 2σ(I)
T_min = 0.504, T_max = 0.526	R_int = 0.024
12180 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 1.17	Δρ_max = 0.32 e Å⁻³
3179 reflections	Δρ_min = −0.90 e Å⁻³
182 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
I	0.388646 (14)	0.197645 (13)	−0.026745 (9)	0.02319 (5)
S	0.80967 (5)	0.78626 (5)	0.39558 (4)	0.01979 (9)
F	1.07549 (17)	0.74121 (17)	0.98010 (11)	0.0369 (3)
O1	0.65247 (16)	0.31158 (15)	0.51009 (11)	0.0203 (2)
O2	0.67539 (17)	0.81288 (17)	0.31415 (13)	0.0269 (3)
C1	0.7317 (2)	0.5608 (2)	0.41682 (15)	0.0185 (3)
C2	0.6277 (2)	0.4171 (2)	0.33021 (15)	0.0176 (3)
C3	0.5720 (2)	0.3991 (2)	0.20821 (15)	0.0195 (3)
H3	0.6019	0.4976	0.1624	0.023*
C4	0.4713 (2)	0.2317 (2)	0.15682 (15)	0.0195 (3)
C5	0.4243 (2)	0.0842 (2)	0.22213 (16)	0.0218 (3)
H5	0.3537	−0.0280	0.1834	0.026*
C6	0.4802 (2)	0.1007 (2)	0.34311 (16)	0.0217 (3)
H6	0.4509	0.0024	0.3889	0.026*
C7	0.5807 (2)	0.2682 (2)	0.39309 (15)	0.0189 (3)
C8	0.7428 (2)	0.4910 (2)	0.52316 (15)	0.0185 (3)
C9	0.8296 (2)	0.5608 (2)	0.64234 (16)	0.0189 (3)
C10	0.7577 (2)	0.4728 (2)	0.74357 (16)	0.0210 (3)
H10	0.6515	0.3708	0.7340	0.025*
C11	0.8411 (2)	0.5344 (2)	0.85731 (17)	0.0240 (3)
H11	0.7935	0.4752	0.9262	0.029*
C12	0.9944 (2)	0.6832 (2)	0.86850 (17)	0.0247 (4)
C13	1.0692 (2)	0.7737 (2)	0.77148 (18)	0.0258 (4)
H13	1.1747	0.8763	0.7823	0.031*
C14	0.9860 (2)	0.7105 (2)	0.65755 (17)	0.0230 (3)
H14	1.0360	0.7697	0.5891	0.028*
C15	0.9920 (3)	0.7971 (3)	0.3035 (2)	0.0335 (4)
H15A	0.9474	0.7159	0.2304	0.050*
H15B	1.0779	0.7646	0.3491	0.050*
H15C	1.0506	0.9166	0.2806	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.03081 (8)	0.02065 (7)	0.01672 (7)	0.00884 (5)	−0.00240 (5)	−0.00103 (4)
S	0.02125 (19)	0.01521 (18)	0.0224 (2)	0.00624 (15)	0.00127 (15)	0.00201 (15)
F	0.0418 (7)	0.0385 (7)	0.0225 (6)	0.0071 (5)	−0.0113 (5)	0.0010 (5)
O1	0.0245 (6)	0.0177 (6)	0.0171 (6)	0.0059 (5)	0.0003 (5)	0.0025 (4)
O2	0.0258 (6)	0.0245 (6)	0.0324 (7)	0.0108 (5)	−0.0005 (5)	0.0085 (5)
C1	0.0200 (7)	0.0166 (7)	0.0185 (8)	0.0067 (6)	0.0011 (6)	0.0009 (6)
C2	0.0188 (7)	0.0157 (7)	0.0188 (8)	0.0070 (6)	0.0021 (6)	0.0012 (6)
C3	0.0235 (8)	0.0182 (7)	0.0175 (8)	0.0086 (6)	0.0009 (6)	0.0026 (6)
C4	0.0225 (8)	0.0210 (8)	0.0159 (8)	0.0095 (6)	0.0008 (6)	0.0001 (6)
C5	0.0238 (8)	0.0190 (8)	0.0210 (9)	0.0067 (6)	0.0021 (6)	−0.0005 (6)
C6	0.0256 (8)	0.0175 (8)	0.0214 (9)	0.0067 (6)	0.0039 (6)	0.0049 (6)
C7	0.0212 (7)	0.0208 (8)	0.0154 (8)	0.0087 (6)	0.0022 (6)	0.0023 (6)
C8	0.0187 (7)	0.0168 (7)	0.0201 (8)	0.0066 (6)	0.0021 (6)	0.0015 (6)
C9	0.0200 (7)	0.0210 (8)	0.0177 (8)	0.0102 (6)	0.0014 (6)	0.0017 (6)
C10	0.0217 (8)	0.0217 (8)	0.0203 (8)	0.0091 (6)	0.0017 (6)	0.0020 (6)
C11	0.0280 (9)	0.0263 (9)	0.0196 (9)	0.0118 (7)	0.0022 (7)	0.0045 (7)
C12	0.0276 (9)	0.0273 (9)	0.0200 (9)	0.0122 (7)	−0.0057 (7)	−0.0004 (7)
C13	0.0220 (8)	0.0261 (9)	0.0257 (9)	0.0058 (7)	−0.0025 (7)	0.0006 (7)
C14	0.0212 (8)	0.0247 (8)	0.0220 (9)	0.0068 (7)	0.0014 (6)	0.0047 (7)
C15	0.0265 (9)	0.0312 (10)	0.0470 (13)	0.0128 (8)	0.0145 (9)	0.0157 (9)

Geometric parameters (Å, º) top

I—C4	2.096 (2)	C6—C7	1.380 (2)
I—O2ⁱ	3.211 (1)	C6—H6	0.9500
S—O2	1.491 (1)	C8—C9	1.455 (2)
S—C1	1.768 (2)	C9—C14	1.397 (2)
S—C15	1.792 (2)	C9—C10	1.403 (2)
F—C12	1.354 (2)	C10—C11	1.385 (3)
O1—C7	1.376 (2)	C10—H10	0.9500
O1—C8	1.381 (2)	C11—C12	1.378 (3)
C1—C8	1.370 (2)	C11—H11	0.9500
C1—C2	1.444 (2)	C12—C13	1.379 (3)
C2—C7	1.394 (2)	C13—C14	1.388 (3)
C2—C3	1.398 (2)	C13—H13	0.9500
C3—C4	1.385 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.401 (2)	C15—H15B	0.9800
C5—C6	1.388 (3)	C15—H15C	0.9800
C5—H5	0.9500

C4—I—O2ⁱ	170.98 (5)	C1—C8—C9	135.10 (16)
O2—S—C1	107.38 (8)	O1—C8—C9	114.45 (14)
O2—S—C15	105.67 (9)	C14—C9—C10	119.35 (16)
C1—S—C15	98.36 (9)	C14—C9—C8	121.35 (16)
C7—O1—C8	106.78 (13)	C10—C9—C8	119.27 (15)
C8—C1—C2	107.00 (14)	C11—C10—C9	120.17 (17)
C8—C1—S	125.99 (13)	C11—C10—H10	119.9
C2—C1—S	126.68 (13)	C9—C10—H10	119.9
C7—C2—C3	119.08 (15)	C12—C11—C10	118.64 (17)
C7—C2—C1	105.32 (14)	C12—C11—H11	120.7
C3—C2—C1	135.60 (15)	C10—C11—H11	120.7
C4—C3—C2	117.23 (15)	F—C12—C11	118.06 (17)
C4—C3—H3	121.4	F—C12—C13	118.91 (17)
C2—C3—H3	121.4	C11—C12—C13	123.02 (17)
C3—C4—C5	122.69 (16)	C12—C13—C14	118.09 (17)
C3—C4—I	118.60 (12)	C12—C13—H13	121.0
C5—C4—I	118.71 (13)	C14—C13—H13	121.0
C6—C5—C4	120.44 (16)	C13—C14—C9	120.72 (17)
C6—C5—H5	119.8	C13—C14—H14	119.6
C4—C5—H5	119.8	C9—C14—H14	119.6
C7—C6—C5	116.26 (16)	S—C15—H15A	109.5
C7—C6—H6	121.9	S—C15—H15B	109.5
C5—C6—H6	121.9	H15A—C15—H15B	109.5
O1—C7—C6	125.22 (15)	S—C15—H15C	109.5
O1—C7—C2	110.46 (14)	H15A—C15—H15C	109.5
C6—C7—C2	124.30 (16)	H15B—C15—H15C	109.5
C1—C8—O1	110.43 (14)

O2—S—C1—C8	−140.15 (15)	C1—C2—C7—C6	−179.85 (16)
C15—S—C1—C8	110.45 (17)	C2—C1—C8—O1	0.04 (18)
O2—S—C1—C2	32.41 (17)	S—C1—C8—O1	173.80 (12)
C15—S—C1—C2	−76.99 (16)	C2—C1—C8—C9	178.16 (17)
C8—C1—C2—C7	0.84 (18)	S—C1—C8—C9	−8.1 (3)
S—C1—C2—C7	−172.87 (13)	C7—O1—C8—C1	−0.91 (18)
C8—C1—C2—C3	−178.44 (18)	C7—O1—C8—C9	−179.46 (13)
S—C1—C2—C3	7.8 (3)	C1—C8—C9—C14	−28.7 (3)
C7—C2—C3—C4	0.3 (2)	O1—C8—C9—C14	149.37 (16)
C1—C2—C3—C4	179.47 (17)	C1—C8—C9—C10	153.29 (19)
C2—C3—C4—C5	0.3 (2)	O1—C8—C9—C10	−28.6 (2)
C2—C3—C4—I	−178.89 (11)	C14—C9—C10—C11	0.1 (2)
C3—C4—C5—C6	−0.8 (3)	C8—C9—C10—C11	178.20 (15)
I—C4—C5—C6	178.41 (13)	C9—C10—C11—C12	0.3 (3)
C4—C5—C6—C7	0.6 (2)	C10—C11—C12—F	−179.46 (16)
C8—O1—C7—C6	179.87 (16)	C10—C11—C12—C13	−0.2 (3)
C8—O1—C7—C2	1.47 (18)	F—C12—C13—C14	178.88 (16)
C5—C6—C7—O1	−178.21 (15)	C11—C12—C13—C14	−0.4 (3)
C5—C6—C7—C2	0.0 (3)	C12—C13—C14—C9	0.8 (3)
C3—C2—C7—O1	177.99 (14)	C10—C9—C14—C13	−0.7 (3)
C1—C2—C7—O1	−1.44 (18)	C8—C9—C14—C13	−178.75 (16)
C3—C2—C7—C6	−0.4 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱⁱ	0.95	2.53	3.432 (2)	158

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀FIO₂S
M_r	400.19
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.1045 (2), 8.2699 (2), 11.0999 (3)
α, β, γ (°)	94.538 (1), 91.118 (1), 111.982 (1)
V (Å³)	686.73 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.49
Crystal size (mm)	0.32 × 0.31 × 0.30

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.504, 0.526
No. of measured, independent and observed [I > 2σ(I)] reflections	12180, 3179, 3130
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.047, 1.17
No. of reflections	3179
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.90

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

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.95	2.53	3.432 (2)	157.9

Symmetry code: (i) −x+1, −y+1, −z+1.

References

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Volume 66| Part 1| January 2010| Page o44

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