organic compounds
5-Iodo-2,7-dimethyl-3-phenylsulfonyl-1-benzofuran
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
The title compound, C16H13IO3S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 76.31 (8)° with the plane of the benzofuran fragment. The is stabilized by aromatic π–π interactions between the furan and benzene rings of neighbouring molecules, and between the benzene rings of neighbouring molecules; the centroid–centroid distances within the stack are 3.700 (4) and 3.788 (4) Å. In addition, the exhibits inter- and intramolecular C—H⋯O interactions, and an I⋯O halogen bond with an I⋯O distance of 3.282 (2) Å and a nearly linear C—I⋯O angle of 165.69 (8)°.
Related literature
For the crystal structures of similar 3-phenylsulfonyl-1-benzofuran compounds, see: Choi et al. (2008a,b). For a review of halogen bonding, see: Politzer et al. (2007).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell 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
10.1107/S1600536808011240/zl2112sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011240/zl2112Isup2.hkl
3-Chloroperoxybenzoic acid (471 mg, 2.1 mmol) was added in small portions to a stirred solution of 5-iodo-2,7-dimethyl 3-phenylsulfanyl-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 δ 2.41 (s, 3H), 2.80 (s, 3H), 7.42 (s, 1H), 7.50–7.32 (m, 3H), 7.98 (d, J = 7.32 Hz, 2H), 8.06 (s, 1H); EI—MS 412 [M+].
(hexane-ethyl acetate, 2: 1 v/v) to afford the title compound as a colorless solid [yield 78%, m.p. 431–432 K; Rf = 0.61 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature. Spectroscopic analysis: 1H NMR (CDCl3, 400 MHz)All H atoms were geometrically positioned and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms, 0.98 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms and 1.5Ueq(C) for methyl H atoms. The highest peak in the difference map is 0.75 Å from I and the largest hole is 0.69 Å from I.
Data collection: SMART (Bruker, 2001); cell
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).C16H13IO3S | F(000) = 808 |
Mr = 412.22 | Dx = 1.815 Mg m−3 |
Monoclinic, P21/n | Melting point = 431–432 K |
Hall symbol: -P_2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1165 (5) Å | Cell parameters from 6912 reflections |
b = 14.0295 (9) Å | θ = 2.9–28.3° |
c = 13.2470 (8) Å | µ = 2.27 mm−1 |
β = 90.320 (1)° | T = 173 K |
V = 1508.42 (16) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.20 × 0.20 mm |
Bruker SMART CCD diffractometer | 3285 independent reflections |
Radiation source: fine-focus sealed tube | 3069 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.0°, θmin = 2.9° |
ϕ and ω scans | h = −10→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | k = −17→16 |
Tmin = 0.579, Tmax = 0.641 | l = −16→16 |
9110 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0428P)2 + 1.8205P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
3285 reflections | Δρmax = 1.13 e Å−3 |
193 parameters | Δρmin = −1.02 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0204 (8) |
C16H13IO3S | V = 1508.42 (16) Å3 |
Mr = 412.22 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.1165 (5) Å | µ = 2.27 mm−1 |
b = 14.0295 (9) Å | T = 173 K |
c = 13.2470 (8) Å | 0.40 × 0.20 × 0.20 mm |
β = 90.320 (1)° |
Bruker SMART CCD diffractometer | 3285 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 3069 reflections with I > 2σ(I) |
Tmin = 0.579, Tmax = 0.641 | Rint = 0.032 |
9110 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 0.99 | Δρmax = 1.13 e Å−3 |
3285 reflections | Δρmin = −1.02 e Å−3 |
193 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
I | 0.01644 (2) | 0.271298 (12) | 0.412327 (13) | 0.03036 (10) | |
S | 0.31859 (7) | 0.47908 (4) | 0.80435 (4) | 0.02106 (14) | |
O1 | 0.3994 (2) | 0.62669 (12) | 0.55765 (13) | 0.0216 (3) | |
O2 | 0.2767 (3) | 0.38039 (13) | 0.79316 (14) | 0.0304 (4) | |
O3 | 0.4628 (2) | 0.50442 (16) | 0.86163 (15) | 0.0343 (4) | |
C1 | 0.3367 (3) | 0.52624 (17) | 0.68298 (18) | 0.0196 (5) | |
C2 | 0.2699 (3) | 0.48622 (17) | 0.59100 (18) | 0.0192 (5) | |
C3 | 0.1833 (3) | 0.40340 (17) | 0.56413 (18) | 0.0216 (5) | |
H3 | 0.1530 | 0.3570 | 0.6128 | 0.026* | |
C4 | 0.1444 (3) | 0.39292 (18) | 0.46308 (19) | 0.0236 (5) | |
C5 | 0.1860 (3) | 0.46045 (18) | 0.39014 (19) | 0.0240 (5) | |
H5 | 0.1549 | 0.4497 | 0.3218 | 0.029* | |
C6 | 0.2718 (3) | 0.54330 (18) | 0.41501 (18) | 0.0224 (5) | |
C7 | 0.3120 (3) | 0.55133 (17) | 0.51657 (18) | 0.0204 (5) | |
C8 | 0.4119 (3) | 0.60993 (18) | 0.65900 (18) | 0.0216 (5) | |
C9 | 0.1490 (3) | 0.53904 (18) | 0.85741 (18) | 0.0240 (5) | |
C10 | 0.1754 (4) | 0.6275 (2) | 0.9019 (2) | 0.0381 (7) | |
H10 | 0.2825 | 0.6548 | 0.9033 | 0.046* | |
C11 | 0.0447 (5) | 0.6749 (3) | 0.9437 (3) | 0.0508 (9) | |
H11 | 0.0610 | 0.7355 | 0.9741 | 0.061* | |
C12 | −0.1097 (5) | 0.6348 (3) | 0.9418 (2) | 0.0497 (10) | |
H12 | −0.1996 | 0.6682 | 0.9707 | 0.060* | |
C13 | −0.1359 (4) | 0.5464 (3) | 0.8984 (2) | 0.0456 (9) | |
H13 | −0.2432 | 0.5193 | 0.8978 | 0.055* | |
C14 | −0.0047 (3) | 0.4970 (2) | 0.85537 (19) | 0.0311 (6) | |
H14 | −0.0207 | 0.4361 | 0.8255 | 0.037* | |
C15 | 0.3140 (4) | 0.6191 (2) | 0.3392 (2) | 0.0308 (6) | |
H15A | 0.2394 | 0.6735 | 0.3474 | 0.046* | |
H15B | 0.3021 | 0.5933 | 0.2708 | 0.046* | |
H15C | 0.4279 | 0.6401 | 0.3500 | 0.046* | |
C16 | 0.4982 (3) | 0.6852 (2) | 0.7172 (2) | 0.0284 (5) | |
H16A | 0.6032 | 0.7001 | 0.6846 | 0.043* | |
H16B | 0.5189 | 0.6626 | 0.7861 | 0.043* | |
H16C | 0.4295 | 0.7426 | 0.7193 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I | 0.02777 (13) | 0.02830 (13) | 0.03502 (14) | −0.00635 (6) | 0.00123 (8) | −0.00964 (7) |
S | 0.0220 (3) | 0.0220 (3) | 0.0192 (3) | 0.0029 (2) | 0.0004 (2) | 0.0016 (2) |
O1 | 0.0229 (8) | 0.0197 (8) | 0.0224 (8) | −0.0016 (7) | 0.0032 (7) | 0.0006 (7) |
O2 | 0.0432 (12) | 0.0204 (9) | 0.0275 (9) | 0.0044 (8) | 0.0045 (8) | 0.0035 (7) |
O3 | 0.0264 (10) | 0.0488 (12) | 0.0277 (9) | −0.0001 (9) | −0.0064 (8) | 0.0021 (9) |
C1 | 0.0192 (11) | 0.0205 (11) | 0.0190 (11) | 0.0006 (9) | 0.0015 (9) | −0.0001 (9) |
C2 | 0.0169 (10) | 0.0208 (11) | 0.0200 (11) | 0.0020 (9) | 0.0024 (8) | −0.0003 (9) |
C3 | 0.0208 (11) | 0.0198 (11) | 0.0243 (11) | −0.0006 (9) | 0.0030 (9) | −0.0005 (9) |
C4 | 0.0196 (11) | 0.0228 (12) | 0.0285 (12) | 0.0002 (9) | 0.0019 (9) | −0.0051 (10) |
C5 | 0.0243 (12) | 0.0274 (12) | 0.0203 (11) | 0.0035 (10) | −0.0015 (9) | −0.0028 (10) |
C6 | 0.0222 (12) | 0.0232 (12) | 0.0219 (11) | 0.0054 (9) | 0.0025 (9) | 0.0018 (10) |
C7 | 0.0178 (11) | 0.0185 (11) | 0.0250 (11) | 0.0004 (8) | 0.0027 (9) | −0.0012 (9) |
C8 | 0.0212 (11) | 0.0213 (11) | 0.0222 (11) | 0.0010 (9) | 0.0028 (9) | −0.0005 (9) |
C9 | 0.0296 (13) | 0.0250 (12) | 0.0174 (10) | 0.0053 (10) | 0.0046 (10) | 0.0042 (9) |
C10 | 0.0479 (18) | 0.0284 (14) | 0.0383 (15) | −0.0016 (13) | 0.0175 (14) | −0.0031 (12) |
C11 | 0.073 (3) | 0.0323 (16) | 0.0474 (19) | 0.0140 (16) | 0.0297 (18) | 0.0001 (14) |
C12 | 0.058 (2) | 0.059 (2) | 0.0323 (16) | 0.0347 (18) | 0.0188 (15) | 0.0125 (15) |
C13 | 0.0245 (14) | 0.085 (3) | 0.0269 (14) | 0.0115 (15) | 0.0020 (11) | 0.0152 (16) |
C14 | 0.0261 (13) | 0.0458 (16) | 0.0214 (12) | 0.0018 (12) | −0.0038 (10) | 0.0030 (11) |
C15 | 0.0378 (15) | 0.0302 (14) | 0.0245 (12) | 0.0014 (11) | 0.0019 (11) | 0.0068 (11) |
C16 | 0.0288 (13) | 0.0264 (13) | 0.0299 (13) | −0.0052 (11) | 0.0018 (10) | −0.0049 (11) |
I—O2i | 3.282 (2) | C8—C16 | 1.481 (3) |
I—C4 | 2.106 (3) | C9—C14 | 1.380 (4) |
S—O2 | 1.433 (2) | C9—C10 | 1.390 (4) |
S—O3 | 1.436 (2) | C10—C11 | 1.371 (4) |
S—C1 | 1.746 (2) | C10—H10 | 0.9500 |
S—C9 | 1.762 (3) | C11—C12 | 1.374 (6) |
O1—C8 | 1.366 (3) | C11—H11 | 0.9500 |
O1—C7 | 1.383 (3) | C12—C13 | 1.383 (6) |
C1—C8 | 1.362 (3) | C12—H12 | 0.9500 |
C1—C2 | 1.444 (3) | C13—C14 | 1.395 (4) |
C2—C7 | 1.388 (3) | C13—H13 | 0.9500 |
C2—C3 | 1.403 (3) | C14—H14 | 0.9500 |
C3—C4 | 1.381 (3) | C15—H15A | 0.9800 |
C3—H3 | 0.9500 | C15—H15B | 0.9800 |
C4—C5 | 1.396 (4) | C15—H15C | 0.9800 |
C5—C6 | 1.394 (4) | C16—H16A | 0.9800 |
C5—H5 | 0.9500 | C16—H16B | 0.9800 |
C6—C7 | 1.387 (3) | C16—H16C | 0.9800 |
C6—C15 | 1.504 (3) | ||
C4—I—O2i | 165.69 (8) | O1—C8—C16 | 114.9 (2) |
O2—S—O3 | 119.1 (1) | C14—C9—C10 | 121.8 (3) |
O2—S—C1 | 107.0 (1) | C14—C9—S | 119.7 (2) |
O3—S—C1 | 108.7 (1) | C10—C9—S | 118.5 (2) |
O2—S—C9 | 108.5 (1) | C11—C10—C9 | 119.1 (3) |
O3—S—C9 | 107.9 (1) | C11—C10—H10 | 120.4 |
C1—S—C9 | 104.9 (1) | C9—C10—H10 | 120.4 |
C8—O1—C7 | 106.9 (2) | C10—C11—C12 | 120.1 (3) |
C8—C1—C2 | 107.7 (2) | C10—C11—H11 | 120.0 |
C8—C1—S | 125.6 (2) | C12—C11—H11 | 120.0 |
C2—C1—S | 126.6 (2) | C11—C12—C13 | 120.9 (3) |
C7—C2—C3 | 119.3 (2) | C11—C12—H12 | 119.6 |
C7—C2—C1 | 104.5 (2) | C13—C12—H12 | 119.6 |
C3—C2—C1 | 136.1 (2) | C12—C13—C14 | 119.9 (3) |
C4—C3—C2 | 116.5 (2) | C12—C13—H13 | 120.0 |
C4—C3—H3 | 121.8 | C14—C13—H13 | 120.0 |
C2—C3—H3 | 121.8 | C9—C14—C13 | 118.2 (3) |
C3—C4—C5 | 122.9 (2) | C9—C14—H14 | 120.9 |
C3—C4—I | 120.4 (2) | C13—C14—H14 | 120.9 |
C5—C4—I | 116.7 (2) | C6—C15—H15A | 109.5 |
C6—C5—C4 | 121.7 (2) | C6—C15—H15B | 109.5 |
C6—C5—H5 | 119.2 | H15A—C15—H15B | 109.5 |
C4—C5—H5 | 119.2 | C6—C15—H15C | 109.5 |
C7—C6—C5 | 114.3 (2) | H15A—C15—H15C | 109.5 |
C7—C6—C15 | 122.5 (2) | H15B—C15—H15C | 109.5 |
C5—C6—C15 | 123.2 (2) | C8—C16—H16A | 109.5 |
O1—C7—C2 | 110.6 (2) | C8—C16—H16B | 109.5 |
O1—C7—C6 | 124.1 (2) | H16A—C16—H16B | 109.5 |
C2—C7—C6 | 125.3 (2) | C8—C16—H16C | 109.5 |
C1—C8—O1 | 110.3 (2) | H16A—C16—H16C | 109.5 |
C1—C8—C16 | 134.8 (2) | H16B—C16—H16C | 109.5 |
O2—S—C1—C8 | −163.4 (2) | C5—C6—C7—O1 | 178.8 (2) |
O3—S—C1—C8 | −33.6 (3) | C15—C6—C7—O1 | −2.7 (4) |
C9—S—C1—C8 | 81.5 (2) | C5—C6—C7—C2 | −1.7 (4) |
O2—S—C1—C2 | 19.2 (2) | C15—C6—C7—C2 | 176.8 (2) |
O3—S—C1—C2 | 149.0 (2) | C2—C1—C8—O1 | −0.4 (3) |
C9—S—C1—C2 | −95.8 (2) | S—C1—C8—O1 | −178.2 (2) |
C8—C1—C2—C7 | 0.1 (3) | C2—C1—C8—C16 | 178.1 (3) |
S—C1—C2—C7 | 177.8 (2) | S—C1—C8—C16 | 0.3 (4) |
C8—C1—C2—C3 | 178.8 (3) | C7—O1—C8—C1 | 0.5 (3) |
S—C1—C2—C3 | −3.4 (4) | C7—O1—C8—C16 | −178.3 (2) |
C7—C2—C3—C4 | −0.4 (3) | O2—S—C9—C14 | −17.4 (2) |
C1—C2—C3—C4 | −179.1 (3) | O3—S—C9—C14 | −147.6 (2) |
C2—C3—C4—C5 | −0.7 (4) | C1—S—C9—C14 | 96.7 (2) |
C2—C3—C4—I | 179.5 (2) | O2—S—C9—C10 | 161.6 (2) |
C3—C4—C5—C6 | 0.7 (4) | O3—S—C9—C10 | 31.4 (2) |
I—C4—C5—C6 | −179.5 (2) | C1—S—C9—C10 | −84.4 (2) |
C4—C5—C6—C7 | 0.5 (4) | C14—C9—C10—C11 | −0.9 (5) |
C4—C5—C6—C15 | −178.0 (2) | S—C9—C10—C11 | −179.8 (3) |
C8—O1—C7—C2 | −0.5 (3) | C9—C10—C11—C12 | 0.3 (5) |
C8—O1—C7—C6 | 179.0 (2) | C10—C11—C12—C13 | 0.3 (5) |
C3—C2—C7—O1 | −178.7 (2) | C11—C12—C13—C14 | −0.3 (5) |
C1—C2—C7—O1 | 0.3 (3) | C10—C9—C14—C13 | 0.8 (4) |
C3—C2—C7—C6 | 1.7 (4) | S—C9—C14—C13 | 179.8 (2) |
C1—C2—C7—C6 | −179.3 (2) | C12—C13—C14—C9 | −0.3 (4) |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1ii | 0.95 | 2.59 | 3.382 (4) | 141 |
C13—H13···O3iii | 0.95 | 2.44 | 3.342 (4) | 159 |
C14—H14···O2 | 0.95 | 2.58 | 2.931 (4) | 103 |
C16—H16B···O3 | 0.98 | 2.48 | 3.191 (4) | 129 |
Symmetry codes: (ii) x−1/2, −y+3/2, z+1/2; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H13IO3S |
Mr | 412.22 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 8.1165 (5), 14.0295 (9), 13.2470 (8) |
β (°) | 90.320 (1) |
V (Å3) | 1508.42 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.27 |
Crystal size (mm) | 0.40 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2000) |
Tmin, Tmax | 0.579, 0.641 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9110, 3285, 3069 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.074, 0.99 |
No. of reflections | 3285 |
No. of parameters | 193 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.13, −1.02 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.95 | 2.59 | 3.382 (4) | 141.3 |
C13—H13···O3ii | 0.95 | 2.44 | 3.342 (4) | 158.6 |
C14—H14···O2 | 0.95 | 2.58 | 2.931 (4) | 102.5 |
C16—H16B···O3 | 0.98 | 2.48 | 3.191 (4) | 129.4 |
Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) x−1, y, z. |
References
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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As a part of our ongoing studies on the synthesis and structure of 3-phenyl-sulfonyl-1-benzofuran analogues, the crystal structure of 5-bromo-2-methyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008a) and 2,5,7-trimethyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008b) have been recently described in the literature. Herein we report the molecular and crystal structure of the title ompound, 5-iodo-2,7-dimethyl-3-phenylsulfonyl-1-benzofuran (Fig. 1).
The benzofuran unit is essentially planar, with a mean deviation of 0.009 Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9—C14) makes a dihedral angle of 76.31 (8)° with the plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by two different π—π interactions within each stack of molecules; one between the furan ring (Cg1) and an adjacent benzene ring (Cg2v) of a benzofuran unit {distance 3.700 (4) Å}, and a second between the benzene ring (Cg2) and an adjacent benzene ring (Cg2iii) of the benzofuran unit {distance 3.788 (4) Å}(Cg1 and Cg2 are the centroids of the O1/C8/C1/C2/C7 furan ring and the C2—C7 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by inter- and intramolecular C—H···O interactions (Table 1), and by a halogen bond (Politzer et al., 2007) between the iodine atom and the oxygen atom of the S═O unit (Fig. 2; symmetry code as in Fig, 2).