Crystal structure of 5-iodo-2-methyl-3-[(4-methyl­phenyl)­sulfon­yl]-1-benzo­furan

Choi, H.D.; Lee, U.

doi:10.1107/S1600536814018510

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Page o1028

doi:10.1107/S1600536814018510

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Crystal structure of 5-iodo-2-methyl-3-[(4-methylphenyl)sulfonyl]-1-benzofuran

Hong Dae Choi ^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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 12 August 2014; accepted 14 August 2014; online 20 August 2014)

In the title compound, C₁₆H₁₃IO₃S, the dihedral angle between the planes of the benzofuran ring system [r.m.s. deviation = 0.015 (2) Å] and the 4-methylphenyl ring is 70.35 (5)°. In the crystal, molecules are linked by pairs of π–π interactions between the furan and benzene rings, with centroid–centroid distances of 3.667 (3) and 3.701 (3) Å. The molecules stack along the a-axis direction. In addition, pairs of C—H⋯O hydrogen bonds between inversion-related dimers [which generate R₂²(10) loops] and a short I⋯I [3.7534 (3) Å] contact are observed.

Keywords: crystal structure; benzofuran; 4-methylphenyl; π–π interactions; C—H⋯O hydrogen bonds; I⋯I interactions.

CCDC reference: 1019339

1. Related literature

For a related structure and background to benzofuran derivatives, see: Choi & Lee (2014 ). For further synthetic details, see: Choi et al. (1999 ).

2. Experimental

2.1. Crystal data

C₁₆H₁₃IO₃S
M_r = 412.22
Triclinic, $[P \overline 1]$
a = 7.2161 (1) Å
b = 10.5267 (2) Å
c = 11.3442 (2) Å
α = 111.540 (1)°
β = 90.882 (1)°
γ = 108.760 (1)°
V = 750.19 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.28 mm⁻¹
T = 173 K
0.45 × 0.37 × 0.33 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.427, T_max = 0.520
13690 measured reflections
3730 independent reflections
3508 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.059
S = 1.09
3730 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O3ⁱ	0.95	2.44	3.311 (2)	153
Symmetry code: (i) -x+1, -y+1, -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

CCDC reference: 1019339

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814018510/hb7273sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018510/hb7273Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018510/hb7273Isup3.cml

checkCIF report

Comment top

As part of our ongoing program of benzofuran derivatives (Choi & Lee, 2014), we report herein 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 0.015 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-methylphenyl ring is essentially planar, with a mean deviation of 0.007 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring and the 4-methylphenyl ring is 70.35 (5)°. In the crystal structure (Fig. 2), molecules are linked by pairs of π–π interactions between the furan and benzene rings of neighbouring molecules. The molecules stack along the a-axis direction. The relevant centroid names for π–π stacking interactions are Cg1 for furan ring (C1/C2/C7/O1/C8) and Cg2 for the benzene ring (C2–C7). The centroid–centroid separations of Cg1···Cg2ⁱⁱⁱ and Cg1···Cg2^iv are 3.667 (3) and 3.701 (3) Å, respectively. The symmetry codes are: (iii) - x, - y, - z + 1; (iv) - x + 1, - y, - z + 1. The slippages of Cg1···Cg2ⁱⁱⁱ and Cg1···Cg2^iv are 1.379 (3) and 1.090 (3) Å, respectively. In the crystal (Fig. 2), C—H···O hydrogen bonds (Table 1) between inversion-related dimers and short I1···I1ⁱⁱ [3.7534 (3) Å] contacts are observed.

Related literature top

For a related structure and background to benzofuran derivatives, see: Choi & Lee (2014). For further synthetic details, see: Choi et al. (1999).

Experimental top

The starting material 5-iodo-2-methyl-3-(4-methylphenylsulfanyl)-1-benzofuran was prepared by literature method (Choi et al. 1999). 3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-iodo-2-methyl-3-(4-methylphenylsulfanyl)-1-benzofuran (342 mg, 0.9 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 10h, the mixture was washed with saturated sodium bicarbonate solution (2 × 20 ml) 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 69% (284 mg); m.p. 461–462 K; R_f = 0.51 (hexane–ethyl acetate, 4:1 v/v)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound (22 mg) in ethtyl acetate (10 ml) 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 displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view of the C—H···O, π–π and I···I 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 + 1, - z + 2; (ii) - x + 1, - y, - z; (iii) - x, - y, - z + 1; (iv) - x + 1, - y, - z + 1.]

5-iodo-2-methyl-3-[(4-methylphenyl)sulfonyl]-1-benzofuran top

Crystal data top

C₁₆H₁₃IO₃S	Z = 2
M_r = 412.22	F(000) = 404
Triclinic, P1	D_x = 1.825 Mg m⁻³
Hall symbol: -P 1	Melting point = 462–461 K
a = 7.2161 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5267 (2) Å	Cell parameters from 9550 reflections
c = 11.3442 (2) Å	θ = 3.0–28.4°
α = 111.540 (1)°	µ = 2.28 mm⁻¹
β = 90.882 (1)°	T = 173 K
γ = 108.760 (1)°	Block, colourless
V = 750.19 (2) Å³	0.45 × 0.37 × 0.33 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3730 independent reflections
Radiation source: rotating anode	3508 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.0°
ϕ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→12
T_min = 0.427, T_max = 0.520	l = −15→15
13690 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) = 0.059	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0251P)² + 0.4508P] where P = (F_o² + 2F_c²)/3
3730 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

C₁₆H₁₃IO₃S	γ = 108.760 (1)°
M_r = 412.22	V = 750.19 (2) Å³
Triclinic, P1	Z = 2
a = 7.2161 (1) Å	Mo Kα radiation
b = 10.5267 (2) Å	µ = 2.28 mm⁻¹
c = 11.3442 (2) Å	T = 173 K
α = 111.540 (1)°	0.45 × 0.37 × 0.33 mm
β = 90.882 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3730 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3508 reflections with I > 2σ(I)
T_min = 0.427, T_max = 0.520	R_int = 0.027
13690 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.09	Δρ_max = 0.53 e Å⁻³
3730 reflections	Δρ_min = −0.82 e Å⁻³
192 parameters

Special details top

Experimental. ¹H NMR (δ p.p.m., CDCl3, 400 Hz): 8.23 (s, 1H), 7.87 (d, J = 8.56 Hz, 2H), 7.58 (dd, J = 8.56 and 1.72 Hz, 1H), 7.32 (d, J = 8.20 Hz, 2H), 7.17 (d, J = 8.56 Hz, 1H), 2.78 (s, 3H), 2.40 (s, 3H).

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	0.34881 (2)	0.005191 (17)	0.133697 (13)	0.03924 (6)
S1	0.51630 (7)	0.39711 (5)	0.72563 (4)	0.02485 (10)
O1	0.1860 (2)	−0.00618 (16)	0.66250 (15)	0.0303 (3)
O2	0.6298 (2)	0.41551 (16)	0.62596 (13)	0.0302 (3)
O3	0.6169 (2)	0.43950 (18)	0.85197 (14)	0.0346 (3)
C1	0.3716 (3)	0.2132 (2)	0.66867 (18)	0.0245 (4)
C2	0.3274 (3)	0.1121 (2)	0.53672 (18)	0.0236 (4)
C3	0.3694 (3)	0.1210 (2)	0.41971 (19)	0.0257 (4)
H3	0.4451	0.2108	0.4148	0.031*
C4	0.2959 (3)	−0.0065 (2)	0.31154 (19)	0.0283 (4)
C5	0.1880 (3)	−0.1412 (2)	0.3154 (2)	0.0329 (4)
H5	0.1444	−0.2267	0.2386	0.040*
C6	0.1449 (3)	−0.1498 (2)	0.4313 (2)	0.0326 (4)
H6	0.0707	−0.2398	0.4364	0.039*
C7	0.2144 (3)	−0.0220 (2)	0.5385 (2)	0.0268 (4)
C8	0.2817 (3)	0.1378 (2)	0.7397 (2)	0.0281 (4)
C9	0.2619 (3)	0.1795 (3)	0.8770 (2)	0.0365 (5)
H9A	0.3626	0.2751	0.9271	0.055*
H9B	0.2802	0.1066	0.9058	0.055*
H9C	0.1299	0.1844	0.8893	0.055*
C10	0.3497 (3)	0.4906 (2)	0.73988 (18)	0.0248 (4)
C11	0.3006 (3)	0.5246 (2)	0.63922 (19)	0.0288 (4)
H11	0.3530	0.4950	0.5615	0.035*
C12	0.1741 (3)	0.6022 (2)	0.6538 (2)	0.0328 (4)
H12	0.1422	0.6274	0.5858	0.039*
C13	0.0926 (3)	0.6441 (2)	0.7656 (2)	0.0309 (4)
C14	0.1398 (3)	0.6056 (2)	0.8638 (2)	0.0345 (5)
H14	0.0825	0.6315	0.9399	0.041*
C15	0.2688 (3)	0.5302 (2)	0.85277 (19)	0.0317 (4)
H15	0.3016	0.5059	0.9211	0.038*
C16	−0.0386 (4)	0.7339 (2)	0.7832 (3)	0.0412 (5)
H16A	0.0429	0.8378	0.8215	0.062*
H16B	−0.1335	0.7112	0.8399	0.062*
H16C	−0.1104	0.7110	0.6998	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.04516 (10)	0.04799 (10)	0.02485 (8)	0.02137 (7)	0.00481 (6)	0.01037 (6)
S1	0.0240 (2)	0.0273 (2)	0.0206 (2)	0.00442 (17)	0.00161 (17)	0.01065 (18)
O1	0.0292 (7)	0.0299 (7)	0.0393 (8)	0.0103 (6)	0.0085 (6)	0.0220 (6)
O2	0.0286 (7)	0.0306 (7)	0.0267 (7)	0.0034 (6)	0.0067 (6)	0.0122 (6)
O3	0.0315 (7)	0.0426 (8)	0.0248 (7)	0.0068 (6)	−0.0035 (6)	0.0135 (6)
C1	0.0223 (8)	0.0273 (9)	0.0269 (9)	0.0090 (7)	0.0047 (7)	0.0137 (8)
C2	0.0197 (8)	0.0248 (9)	0.0292 (9)	0.0091 (7)	0.0029 (7)	0.0128 (7)
C3	0.0245 (9)	0.0259 (9)	0.0277 (9)	0.0085 (7)	0.0032 (7)	0.0119 (8)
C4	0.0269 (9)	0.0314 (10)	0.0281 (10)	0.0144 (8)	0.0017 (7)	0.0100 (8)
C5	0.0312 (10)	0.0265 (10)	0.0369 (11)	0.0121 (8)	−0.0046 (8)	0.0065 (8)
C6	0.0278 (10)	0.0237 (9)	0.0472 (12)	0.0083 (8)	0.0008 (9)	0.0158 (9)
C7	0.0224 (8)	0.0287 (9)	0.0355 (10)	0.0106 (7)	0.0043 (7)	0.0182 (8)
C8	0.0256 (9)	0.0328 (10)	0.0335 (10)	0.0126 (8)	0.0057 (8)	0.0192 (8)
C9	0.0394 (12)	0.0470 (13)	0.0352 (11)	0.0175 (10)	0.0129 (9)	0.0269 (10)
C10	0.0285 (9)	0.0209 (8)	0.0216 (8)	0.0046 (7)	0.0016 (7)	0.0084 (7)
C11	0.0320 (10)	0.0302 (10)	0.0222 (9)	0.0064 (8)	0.0042 (7)	0.0120 (8)
C12	0.0351 (11)	0.0312 (10)	0.0325 (11)	0.0065 (8)	0.0004 (8)	0.0176 (9)
C13	0.0280 (9)	0.0198 (9)	0.0388 (11)	0.0024 (7)	0.0036 (8)	0.0103 (8)
C14	0.0426 (12)	0.0287 (10)	0.0300 (10)	0.0121 (9)	0.0111 (9)	0.0094 (8)
C15	0.0427 (11)	0.0307 (10)	0.0212 (9)	0.0113 (9)	0.0047 (8)	0.0111 (8)
C16	0.0402 (12)	0.0277 (11)	0.0558 (15)	0.0123 (9)	0.0077 (11)	0.0161 (10)

Geometric parameters (Å, º) top

I1—C4	2.099 (2)	C8—C9	1.478 (3)
I1—I1ⁱ	3.7534 (3)	C9—H9A	0.9800
S1—O3	1.4389 (14)	C9—H9B	0.9800
S1—O2	1.4400 (14)	C9—H9C	0.9800
S1—C1	1.737 (2)	C10—C11	1.388 (3)
S1—C10	1.758 (2)	C10—C15	1.394 (3)
O1—C8	1.369 (3)	C11—C12	1.383 (3)
O1—C7	1.381 (3)	C11—H11	0.9500
C1—C8	1.362 (3)	C12—C13	1.388 (3)
C1—C2	1.439 (3)	C12—H12	0.9500
C2—C7	1.393 (3)	C13—C14	1.389 (3)
C2—C3	1.396 (3)	C13—C16	1.507 (3)
C3—C4	1.379 (3)	C14—C15	1.384 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.398 (3)	C15—H15	0.9500
C5—C6	1.384 (3)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.374 (3)	C16—H16C	0.9800
C6—H6	0.9500

C4—I1—I1ⁱ	152.81 (5)	O1—C8—C9	115.80 (17)
O3—S1—O2	119.63 (9)	C8—C9—H9A	109.5
O3—S1—C1	108.45 (10)	C8—C9—H9B	109.5
O2—S1—C1	106.07 (9)	H9A—C9—H9B	109.5
O3—S1—C10	107.93 (10)	C8—C9—H9C	109.5
O2—S1—C10	108.10 (9)	H9A—C9—H9C	109.5
C1—S1—C10	105.86 (9)	H9B—C9—H9C	109.5
C8—O1—C7	107.15 (15)	C11—C10—C15	120.7 (2)
C8—C1—C2	107.56 (17)	C11—C10—S1	119.87 (16)
C8—C1—S1	126.69 (16)	C15—C10—S1	119.40 (16)
C2—C1—S1	125.74 (14)	C12—C11—C10	118.98 (19)
C7—C2—C3	119.25 (18)	C12—C11—H11	120.5
C7—C2—C1	105.06 (17)	C10—C11—H11	120.5
C3—C2—C1	135.69 (17)	C11—C12—C13	121.5 (2)
C4—C3—C2	116.96 (18)	C11—C12—H12	119.3
C4—C3—H3	121.5	C13—C12—H12	119.3
C2—C3—H3	121.5	C12—C13—C14	118.5 (2)
C3—C4—C5	123.1 (2)	C12—C13—C16	121.3 (2)
C3—C4—I1	117.72 (15)	C14—C13—C16	120.1 (2)
C5—C4—I1	119.19 (15)	C15—C14—C13	121.3 (2)
C6—C5—C4	119.9 (2)	C15—C14—H14	119.4
C6—C5—H5	120.0	C13—C14—H14	119.4
C4—C5—H5	120.0	C14—C15—C10	118.99 (19)
C7—C6—C5	116.79 (19)	C14—C15—H15	120.5
C7—C6—H6	121.6	C10—C15—H15	120.5
C5—C6—H6	121.6	C13—C16—H16A	109.5
C6—C7—O1	126.11 (18)	C13—C16—H16B	109.5
C6—C7—C2	123.91 (19)	H16A—C16—H16B	109.5
O1—C7—C2	109.97 (17)	C13—C16—H16C	109.5
C1—C8—O1	110.23 (18)	H16A—C16—H16C	109.5
C1—C8—C9	133.9 (2)	H16B—C16—H16C	109.5

O3—S1—C1—C8	31.6 (2)	C3—C2—C7—O1	−178.42 (16)
O2—S1—C1—C8	161.28 (18)	C1—C2—C7—O1	1.1 (2)
C10—S1—C1—C8	−84.0 (2)	C2—C1—C8—O1	1.4 (2)
O3—S1—C1—C2	−147.56 (17)	S1—C1—C8—O1	−177.87 (14)
O2—S1—C1—C2	−17.9 (2)	C2—C1—C8—C9	−176.3 (2)
C10—S1—C1—C2	96.83 (18)	S1—C1—C8—C9	4.4 (4)
C8—C1—C2—C7	−1.5 (2)	C7—O1—C8—C1	−0.7 (2)
S1—C1—C2—C7	177.78 (15)	C7—O1—C8—C9	177.42 (17)
C8—C1—C2—C3	177.9 (2)	O3—S1—C10—C11	151.02 (16)
S1—C1—C2—C3	−2.8 (3)	O2—S1—C10—C11	20.28 (18)
C7—C2—C3—C4	−0.5 (3)	C1—S1—C10—C11	−93.02 (17)
C1—C2—C3—C4	−179.8 (2)	O3—S1—C10—C15	−28.79 (18)
C2—C3—C4—C5	−1.6 (3)	O2—S1—C10—C15	−159.52 (15)
C2—C3—C4—I1	178.02 (14)	C1—S1—C10—C15	87.17 (17)
I1ⁱ—I1—C4—C3	89.06 (19)	C15—C10—C11—C12	1.8 (3)
I1ⁱ—I1—C4—C5	−91.27 (19)	S1—C10—C11—C12	−178.00 (15)
C3—C4—C5—C6	2.3 (3)	C10—C11—C12—C13	−1.3 (3)
I1—C4—C5—C6	−177.38 (15)	C11—C12—C13—C14	−0.4 (3)
C4—C5—C6—C7	−0.6 (3)	C11—C12—C13—C16	177.49 (19)
C5—C6—C7—O1	179.13 (19)	C12—C13—C14—C15	1.5 (3)
C5—C6—C7—C2	−1.5 (3)	C16—C13—C14—C15	−176.3 (2)
C8—O1—C7—C6	179.2 (2)	C13—C14—C15—C10	−1.0 (3)
C8—O1—C7—C2	−0.3 (2)	C11—C10—C15—C14	−0.7 (3)
C3—C2—C7—C6	2.1 (3)	S1—C10—C15—C14	179.13 (16)
C1—C2—C7—C6	−178.35 (19)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3ⁱⁱ	0.95	2.44	3.311 (2)	153

Symmetry code: (ii) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3ⁱ	0.95	2.44	3.311 (2)	153

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

References

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. & Lee, U. (2014). Acta Cryst. E70, o1018–o1019. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J. & Son, B. W. (1999). J. Korean Chem. Soc. 43, 606–608. CAS 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

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Volume 70| Part 9| September 2014| Page o1028

doi:10.1107/S1600536814018510

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 5-iodo-2-methyl-3-[(4-methyl­phenyl)­sulfon­yl]-1-benzo­furan

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 5-iodo-2-methyl-3-[(4-methylphenyl)sulfonyl]-1-benzofuran