5-Iodo-7-methyl-3-methyl­sulfinyl-2-phenyl-1-benzofuran

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

doi:10.1107/S1600536808014694

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1116

doi:10.1107/S1600536808014694

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5-Iodo-7-methyl-3-methylsulfinyl-2-phenyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byung Ki Kim,^b Byeng Wha Son ^c and Uk Lee ^c ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, ^bDepartment of Molecular Biology, Dongeui University, San 24 Kaya-dong Busanjin-ku, Busan 614-714, Republic of Korea, and ^cDepartment 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 14 May 2008; accepted 15 May 2008; online 21 May 2008)

The title compound, C₁₆H₁₃IO₂S, was prepared by the oxidation of 5-iodo-7-methyl-3-methylsulfanyl-2-phenyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 27.17 (9)° with the plane of the benzofuran fragment, with the O atom and the methyl group of the methylsulfinyl substituent lying on opposite sides of this plane. The crystal structure exhibits intermolecular C—H⋯I interactions, and an I⋯O halogen bond of 3.107 (2) Å with a nearly linear C—I⋯O angle of 173.73 (6)°.

Related literature

For the crystal structures of similar 5-halo-3-methylsulfinyl-2-phenyl-1-benzofuran compounds, see: Choi et al. (2007a ,b ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₃IO₂S
M_r = 396.22
Monoclinic, P 2₁ /c
a = 10.385 (5) Å
b = 17.174 (8) Å
c = 8.943 (4) Å
β = 112.847 (7)°
V = 1469.9 (12) Å³
Z = 4
Mo Kα radiation
μ = 2.32 mm⁻¹
T = 173 (2) K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.572, T_max = 0.623
11429 measured reflections
2877 independent reflections
2706 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.053
S = 1.06
2877 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Iⁱ	0.95	3.06	3.954 (3)	157
Symmetry code: (i) -x, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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/S1600536808014694/zl2118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014694/zl2118Isup2.hkl

checkCIF report

Comment top

This work is related to our previous communications on the synthesis and structure of 5-halo-3-methylsulfinyl-2-phenyl-1-benzofuran analogues, viz. 5-bromo-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007a) and 5-iodo-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007b). Here we report the crystal structure of the title compound, 5-iodo-7-methyl-3-methylsulfinyl-2-phenyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.013 Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9-C14) makes a dihedral angle of 27.17 (9)° with the plane of the benzofuran fragment. The molecular packing (Fig. 2) is stabilized by intermolecular C—H···I interactions (Table 1), and by an I···O halogen bond (Politzer et al., 2007) between the iodine atom and the oxygen of a neighbouring S═O unit, with an I···O2ⁱ distance of 3.107 (2) Å (symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar 5-halo-3-methylsulfinyl-2-phenyl-1-benzofuran compounds, see: Choi et al. (2007a,b). 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 5-iodo-7-methyl-3-methylsulfanyl-2-phenyl-1-benzofuran (380 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 4 h at room temperature, 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 79%, m.p. 433-434 K; R_f = 0.51 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in tetrahydrofuran at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.53 (s, 3H), 3.11 (s, 3H), 7.49-7.58 (m, 4H), 7.83 (dd, J = 8.04 Hz and 1.84 Hz, 2H), 8.39 (s, 1H); EI-MS 396 [M⁺].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. C—H···I interaction and I···O halogen bond (dotted lines) in the title compound. [Symmetry code: (i) -x, -y+1, -z.]

5-Iodo-7-methyl-3-methylsulfinyl-2-phenyl-1-benzofuran top

Crystal data top

C₁₆H₁₃IO₂S	F(000) = 776
M_r = 396.22	D_x = 1.790 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9956 reflections
a = 10.385 (5) Å	θ = 2.1–28.4°
b = 17.174 (8) Å	µ = 2.32 mm⁻¹
c = 8.943 (4) Å	T = 173 K
β = 112.847 (7)°	Block, colorless
V = 1469.9 (12) Å³	0.40 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2877 independent reflections
Radiation source: fine-focus sealed tube	2706 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.4°
ϕ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −21→21
T_min = 0.572, T_max = 0.623	l = −11→11
11429 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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.053	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0278P)² + 0.8832P] where P = (F_o² + 2F_c²)/3
2877 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₁₆H₁₃IO₂S	V = 1469.9 (12) Å³
M_r = 396.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.385 (5) Å	µ = 2.32 mm⁻¹
b = 17.174 (8) Å	T = 173 K
c = 8.943 (4) Å	0.40 × 0.20 × 0.20 mm
β = 112.847 (7)°

Data collection top

Bruker SMART CCD diffractometer	2877 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2706 reflections with I > 2σ(I)
T_min = 0.572, T_max = 0.623	R_int = 0.032
11429 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.053	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
2877 reflections	Δρ_min = −0.66 e Å⁻³
183 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	−0.043288 (13)	0.558358 (8)	0.210981 (16)	0.02333 (7)
S	0.36162 (5)	0.29269 (3)	0.14788 (6)	0.02051 (11)
O1	0.50724 (14)	0.38231 (8)	0.59241 (16)	0.0184 (3)
O2	0.30733 (17)	0.35243 (9)	0.01551 (18)	0.0280 (3)
C1	0.3955 (2)	0.34115 (11)	0.3340 (2)	0.0186 (4)
C2	0.3154 (2)	0.40433 (12)	0.3616 (2)	0.0185 (4)
C3	0.1901 (2)	0.44237 (11)	0.2685 (3)	0.0199 (4)
H3	0.1385	0.4291	0.1581	0.024*
C4	0.1451 (2)	0.50027 (12)	0.3454 (2)	0.0203 (4)
C5	0.2211 (2)	0.52118 (12)	0.5084 (2)	0.0211 (4)
H5	0.1866	0.5614	0.5556	0.025*
C6	0.3460 (2)	0.48423 (11)	0.6021 (2)	0.0195 (4)
C7	0.3883 (2)	0.42659 (12)	0.5218 (2)	0.0182 (4)
C8	0.5095 (2)	0.32999 (11)	0.4756 (2)	0.0180 (4)
C9	0.6257 (2)	0.27448 (12)	0.5307 (2)	0.0184 (4)
C10	0.7494 (2)	0.29442 (13)	0.6599 (3)	0.0267 (5)
H10	0.7591	0.3445	0.7082	0.032*
C11	0.8579 (2)	0.24128 (14)	0.7177 (3)	0.0357 (6)
H11	0.9417	0.2550	0.8061	0.043*
C12	0.8452 (2)	0.16800 (14)	0.6474 (3)	0.0333 (5)
H12	0.9199	0.1317	0.6875	0.040*
C13	0.7229 (2)	0.14820 (13)	0.5185 (3)	0.0284 (5)
H13	0.7144	0.0984	0.4693	0.034*
C14	0.6129 (2)	0.20047 (12)	0.4608 (3)	0.0242 (4)
H14	0.5287	0.1861	0.3738	0.029*
C15	0.4267 (2)	0.50275 (13)	0.7788 (3)	0.0265 (5)
H15A	0.4092	0.4624	0.8460	0.040*
H15B	0.3967	0.5534	0.8043	0.040*
H15C	0.5268	0.5046	0.8010	0.040*
C16	0.2127 (2)	0.23678 (14)	0.1402 (3)	0.0310 (5)
H16A	0.1375	0.2721	0.1369	0.046*
H16B	0.2391	0.2037	0.2369	0.046*
H16C	0.1803	0.2041	0.0428	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.01881 (9)	0.02267 (10)	0.02713 (10)	0.00497 (5)	0.00739 (7)	0.00177 (5)
S	0.0221 (3)	0.0235 (3)	0.0161 (2)	0.0048 (2)	0.00748 (19)	−0.00083 (18)
O1	0.0190 (7)	0.0184 (7)	0.0170 (6)	0.0028 (5)	0.0060 (6)	−0.0001 (5)
O2	0.0330 (9)	0.0325 (8)	0.0175 (7)	0.0065 (7)	0.0088 (6)	0.0050 (6)
C1	0.0197 (9)	0.0193 (10)	0.0179 (9)	0.0009 (8)	0.0084 (8)	−0.0004 (7)
C2	0.0194 (9)	0.0184 (9)	0.0193 (9)	0.0006 (8)	0.0094 (8)	0.0015 (7)
C3	0.0199 (10)	0.0203 (10)	0.0187 (10)	0.0017 (8)	0.0067 (8)	0.0017 (7)
C4	0.0170 (9)	0.0227 (10)	0.0215 (10)	0.0023 (8)	0.0077 (8)	0.0038 (8)
C5	0.0248 (10)	0.0186 (10)	0.0226 (10)	0.0023 (8)	0.0123 (9)	−0.0007 (8)
C6	0.0233 (10)	0.0180 (9)	0.0193 (10)	−0.0003 (8)	0.0105 (8)	0.0006 (7)
C7	0.0185 (10)	0.0169 (9)	0.0194 (10)	−0.0004 (8)	0.0075 (8)	0.0025 (7)
C8	0.0205 (10)	0.0174 (9)	0.0181 (9)	−0.0016 (8)	0.0096 (8)	−0.0008 (7)
C9	0.0177 (9)	0.0206 (10)	0.0186 (9)	0.0003 (8)	0.0090 (8)	0.0040 (7)
C10	0.0219 (11)	0.0215 (10)	0.0324 (12)	−0.0011 (9)	0.0057 (9)	−0.0006 (9)
C11	0.0186 (11)	0.0308 (12)	0.0452 (14)	0.0026 (9)	−0.0013 (10)	0.0021 (10)
C12	0.0233 (11)	0.0274 (12)	0.0478 (14)	0.0080 (9)	0.0121 (11)	0.0091 (10)
C13	0.0324 (12)	0.0209 (10)	0.0338 (12)	0.0036 (9)	0.0150 (10)	0.0013 (9)
C14	0.0251 (11)	0.0232 (10)	0.0234 (10)	0.0010 (9)	0.0086 (9)	−0.0003 (8)
C15	0.0320 (12)	0.0269 (11)	0.0190 (10)	0.0020 (9)	0.0080 (9)	−0.0031 (8)
C16	0.0315 (12)	0.0311 (12)	0.0278 (11)	−0.0070 (10)	0.0087 (10)	−0.0055 (9)

Geometric parameters (Å, º) top

I—C4	2.107 (2)	C8—C9	1.465 (3)
I—O2ⁱ	3.107 (2)	C9—C10	1.396 (3)
S—O2	1.501 (2)	C9—C14	1.400 (3)
S—C1	1.770 (2)	C10—C11	1.385 (3)
S—C16	1.799 (2)	C10—H10	0.9500
O1—C7	1.377 (2)	C11—C12	1.390 (4)
O1—C8	1.385 (2)	C11—H11	0.9500
C1—C8	1.370 (3)	C12—C13	1.386 (3)
C1—C2	1.446 (3)	C12—H12	0.9500
C2—C7	1.389 (3)	C13—C14	1.385 (3)
C2—C3	1.404 (3)	C13—H13	0.9500
C3—C4	1.389 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.409 (3)	C15—H15B	0.9800
C5—C6	1.394 (3)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.391 (3)	C16—H16B	0.9800
C6—C15	1.507 (3)	C16—H16C	0.9800

C4—I—O2ⁱ	173.73 (6)	C10—C9—C8	119.45 (19)
O2—S—C1	107.27 (10)	C14—C9—C8	121.16 (18)
O2—S—C16	106.30 (11)	C11—C10—C9	120.1 (2)
C1—S—C16	98.10 (10)	C11—C10—H10	120.0
C7—O1—C8	106.69 (15)	C9—C10—H10	120.0
C8—C1—C2	107.15 (17)	C10—C11—C12	120.5 (2)
C8—C1—S	126.05 (16)	C10—C11—H11	119.8
C2—C1—S	126.59 (15)	C12—C11—H11	119.8
C7—C2—C3	119.48 (19)	C13—C12—C11	119.6 (2)
C7—C2—C1	105.27 (17)	C13—C12—H12	120.2
C3—C2—C1	135.23 (19)	C11—C12—H12	120.2
C4—C3—C2	116.85 (19)	C14—C13—C12	120.5 (2)
C4—C3—H3	121.6	C14—C13—H13	119.7
C2—C3—H3	121.6	C12—C13—H13	119.7
C3—C4—C5	122.24 (19)	C13—C14—C9	120.0 (2)
C3—C4—I	118.20 (15)	C13—C14—H14	120.0
C5—C4—I	119.56 (15)	C9—C14—H14	120.0
C6—C5—C4	121.56 (19)	C6—C15—H15A	109.5
C6—C5—H5	119.2	C6—C15—H15B	109.5
C4—C5—H5	119.2	H15A—C15—H15B	109.5
C5—C6—C7	114.84 (18)	C6—C15—H15C	109.5
C5—C6—C15	122.91 (19)	H15A—C15—H15C	109.5
C7—C6—C15	122.21 (19)	H15B—C15—H15C	109.5
O1—C7—C2	110.71 (17)	S—C16—H16A	109.5
O1—C7—C6	124.27 (18)	S—C16—H16B	109.5
C2—C7—C6	125.00 (19)	H16A—C16—H16B	109.5
C1—C8—O1	110.17 (17)	S—C16—H16C	109.5
C1—C8—C9	134.83 (18)	H16A—C16—H16C	109.5
O1—C8—C9	114.93 (16)	H16B—C16—H16C	109.5
C10—C9—C14	119.33 (19)

O2—S—C1—C8	−138.12 (18)	C5—C6—C7—O1	−179.08 (18)
C16—S—C1—C8	111.9 (2)	C15—C6—C7—O1	−1.3 (3)
O2—S—C1—C2	36.1 (2)	C5—C6—C7—C2	−0.8 (3)
C16—S—C1—C2	−73.9 (2)	C15—C6—C7—C2	176.9 (2)
C8—C1—C2—C7	−0.4 (2)	C2—C1—C8—O1	0.0 (2)
S—C1—C2—C7	−175.49 (15)	S—C1—C8—O1	175.08 (14)
C8—C1—C2—C3	−179.1 (2)	C2—C1—C8—C9	176.7 (2)
S—C1—C2—C3	5.9 (3)	S—C1—C8—C9	−8.2 (3)
C7—C2—C3—C4	−1.1 (3)	C7—O1—C8—C1	0.5 (2)
C1—C2—C3—C4	177.4 (2)	C7—O1—C8—C9	−176.98 (16)
C2—C3—C4—C5	0.8 (3)	C1—C8—C9—C10	157.6 (2)
C2—C3—C4—I	−179.53 (14)	O1—C8—C9—C10	−25.8 (3)
C3—C4—C5—C6	−0.5 (3)	C1—C8—C9—C14	−25.2 (3)
I—C4—C5—C6	179.82 (15)	O1—C8—C9—C14	151.38 (18)
C4—C5—C6—C7	0.5 (3)	C14—C9—C10—C11	0.0 (3)
C4—C5—C6—C15	−177.3 (2)	C8—C9—C10—C11	177.3 (2)
C8—O1—C7—C2	−0.7 (2)	C9—C10—C11—C12	0.4 (4)
C8—O1—C7—C6	177.71 (19)	C10—C11—C12—C13	0.0 (4)
C3—C2—C7—O1	179.63 (17)	C11—C12—C13—C14	−0.8 (4)
C1—C2—C7—O1	0.7 (2)	C12—C13—C14—C9	1.2 (3)
C3—C2—C7—C6	1.2 (3)	C10—C9—C14—C13	−0.8 (3)
C1—C2—C7—C6	−177.73 (19)	C8—C9—C14—C13	−178.01 (19)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Iⁱ	0.95	3.06	3.954 (3)	157

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃IO₂S
M_r	396.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	10.385 (5), 17.174 (8), 8.943 (4)
β (°)	112.847 (7)
V (Å³)	1469.9 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.32
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.572, 0.623
No. of measured, independent and observed [I > 2σ(I)] reflections	11429, 2877, 2706
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.053, 1.07
No. of reflections	2877
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.66

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C3—H3···Iⁱ	0.95	3.06	3.954 (3)	156.8

Symmetry code: (i) −x, −y+1, −z.

References

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Volume 64| Part 6| June 2008| Page o1116

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