




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809024556/ng2605sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809024556/ng2605Isup2.hkl |
CCDC reference: 744334
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.017
- wR factor = 0.044
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact I .. O2 .. 3.12 Ang.
Author Response: : Explained in the Abstract and Comment as Halogen bond. |
Alert level C SHFSU01_ALERT_2_C Test not performed. _refine_ls_shift/su_max and _refine_ls_shift/esd_max not present. Absolute value of the parameter shift to su ratio given 0.001
Alert level G PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 = 3 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 273 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 273 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The 77% 3-chloroperoxybenzoic acid (123 mg, 0.55 mmol) was added in small portions to a stirred solution of 5-iodo-2-phenyl-3-phenylsulfanyl-1-benzofuran (214 mg, 0.5 mmol) in dichloromethane (30 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 423-424 K; Rf = 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 acetone at room temperature.
All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 Å for aromatic H atoms and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms.
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).
C20H13IO2S | Z = 2 |
Mr = 444.26 | F(000) = 436 |
Triclinic, P1 | Dx = 1.741 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3544 (4) Å | Cell parameters from 6672 reflections |
b = 9.7565 (5) Å | θ = 2.2–27.5° |
c = 10.2808 (5) Å | µ = 2.02 mm−1 |
α = 113.381 (1)° | T = 273 K |
β = 92.640 (1)° | Block, colorless |
γ = 98.047 (1)° | 0.40 × 0.40 × 0.20 mm |
V = 847.42 (7) Å3 |
Bruker SMART CCD diffractometer | 3616 independent reflections |
Radiation source: fine-focus sealed tube | 3503 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.0°, θmin = 2.2° |
ϕ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | k = −12→12 |
Tmin = 0.467, Tmax = 0.665 | l = −13→12 |
7217 measured reflections |
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)] = 0.017 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.044 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0224P)2 + 0.4472P] where P = (Fo2 + 2Fc2)/3 |
3616 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
C20H13IO2S | γ = 98.047 (1)° |
Mr = 444.26 | V = 847.42 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3544 (4) Å | Mo Kα radiation |
b = 9.7565 (5) Å | µ = 2.02 mm−1 |
c = 10.2808 (5) Å | T = 273 K |
α = 113.381 (1)° | 0.40 × 0.40 × 0.20 mm |
β = 92.640 (1)° |
Bruker SMART CCD diffractometer | 3616 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | 3503 reflections with I > 2σ(I) |
Tmin = 0.467, Tmax = 0.665 | Rint = 0.014 |
7217 measured reflections |
R[F2 > 2σ(F2)] = 0.017 | 0 restraints |
wR(F2) = 0.044 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.39 e Å−3 |
3616 reflections | Δρmin = −0.66 e Å−3 |
217 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
I | 0.041308 (11) | 0.682844 (11) | 0.391884 (12) | 0.02610 (5) | |
S | 0.15151 (4) | 0.00846 (5) | 0.27065 (4) | 0.02113 (8) | |
O1 | 0.23863 (13) | 0.11727 (14) | −0.05193 (12) | 0.0244 (2) | |
O2 | 0.01344 (13) | 0.05325 (15) | 0.32919 (13) | 0.0278 (3) | |
C1 | 0.19488 (18) | 0.09925 (19) | 0.15550 (17) | 0.0213 (3) | |
C2 | 0.16806 (17) | 0.24593 (19) | 0.16717 (17) | 0.0212 (3) | |
C3 | 0.12402 (18) | 0.37088 (19) | 0.27157 (18) | 0.0229 (3) | |
H3 | 0.1038 | 0.3714 | 0.3595 | 0.027* | |
C4 | 0.11164 (18) | 0.49421 (19) | 0.23915 (18) | 0.0231 (3) | |
C5 | 0.14158 (19) | 0.4962 (2) | 0.10730 (19) | 0.0263 (3) | |
H5 | 0.1329 | 0.5815 | 0.0901 | 0.032* | |
C6 | 0.1841 (2) | 0.3719 (2) | 0.00232 (19) | 0.0274 (4) | |
H6 | 0.2037 | 0.3707 | −0.0860 | 0.033* | |
C7 | 0.19590 (18) | 0.24964 (19) | 0.03641 (18) | 0.0231 (3) | |
C8 | 0.23701 (18) | 0.02755 (19) | 0.02314 (17) | 0.0222 (3) | |
C9 | 0.28197 (18) | −0.11933 (19) | −0.05014 (18) | 0.0223 (3) | |
C10 | 0.23677 (19) | −0.2044 (2) | −0.19558 (19) | 0.0265 (3) | |
H10 | 0.1800 | −0.1671 | −0.2463 | 0.032* | |
C11 | 0.2777 (2) | −0.3454 (2) | −0.2632 (2) | 0.0315 (4) | |
H11 | 0.2461 | −0.4036 | −0.3592 | 0.038* | |
C12 | 0.3653 (2) | −0.4000 (2) | −0.1890 (2) | 0.0347 (4) | |
H12 | 0.3929 | −0.4939 | −0.2355 | 0.042* | |
C13 | 0.4117 (2) | −0.3148 (2) | −0.0455 (2) | 0.0344 (4) | |
H13 | 0.4706 | −0.3515 | 0.0041 | 0.041* | |
C14 | 0.3700 (2) | −0.1747 (2) | 0.0242 (2) | 0.0286 (4) | |
H14 | 0.4009 | −0.1178 | 0.1206 | 0.034* | |
C15 | 0.29386 (18) | 0.10909 (19) | 0.41498 (17) | 0.0216 (3) | |
C16 | 0.4258 (2) | 0.1827 (2) | 0.3995 (2) | 0.0333 (4) | |
H16 | 0.4411 | 0.1914 | 0.3142 | 0.040* | |
C17 | 0.5347 (2) | 0.2429 (3) | 0.5131 (2) | 0.0412 (5) | |
H17 | 0.6233 | 0.2931 | 0.5041 | 0.049* | |
C18 | 0.5124 (2) | 0.2288 (2) | 0.6400 (2) | 0.0342 (4) | |
H18 | 0.5864 | 0.2684 | 0.7152 | 0.041* | |
C19 | 0.3803 (2) | 0.1560 (2) | 0.65465 (19) | 0.0287 (4) | |
H19 | 0.3655 | 0.1473 | 0.7400 | 0.034* | |
C20 | 0.26963 (19) | 0.09587 (19) | 0.54241 (18) | 0.0244 (3) | |
H20 | 0.1805 | 0.0474 | 0.5523 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I | 0.02785 (7) | 0.02109 (7) | 0.03128 (7) | 0.00645 (4) | 0.00755 (5) | 0.01148 (5) |
S | 0.02433 (19) | 0.02144 (19) | 0.02157 (18) | 0.00522 (15) | 0.00503 (15) | 0.01221 (15) |
O1 | 0.0307 (6) | 0.0269 (6) | 0.0205 (5) | 0.0099 (5) | 0.0065 (5) | 0.0129 (5) |
O2 | 0.0216 (6) | 0.0364 (7) | 0.0300 (6) | 0.0054 (5) | 0.0069 (5) | 0.0178 (6) |
C1 | 0.0226 (7) | 0.0228 (8) | 0.0218 (7) | 0.0055 (6) | 0.0034 (6) | 0.0120 (6) |
C2 | 0.0206 (7) | 0.0244 (8) | 0.0222 (7) | 0.0045 (6) | 0.0026 (6) | 0.0130 (6) |
C3 | 0.0241 (8) | 0.0257 (8) | 0.0228 (8) | 0.0058 (6) | 0.0054 (6) | 0.0133 (7) |
C4 | 0.0213 (8) | 0.0225 (8) | 0.0268 (8) | 0.0049 (6) | 0.0042 (6) | 0.0107 (7) |
C5 | 0.0285 (8) | 0.0267 (9) | 0.0306 (9) | 0.0068 (7) | 0.0027 (7) | 0.0182 (7) |
C6 | 0.0324 (9) | 0.0342 (9) | 0.0242 (8) | 0.0100 (7) | 0.0064 (7) | 0.0190 (7) |
C7 | 0.0235 (8) | 0.0271 (8) | 0.0223 (8) | 0.0071 (6) | 0.0038 (6) | 0.0129 (7) |
C8 | 0.0223 (7) | 0.0264 (8) | 0.0219 (8) | 0.0052 (6) | 0.0022 (6) | 0.0137 (7) |
C9 | 0.0215 (7) | 0.0250 (8) | 0.0228 (8) | 0.0045 (6) | 0.0063 (6) | 0.0115 (7) |
C10 | 0.0267 (8) | 0.0279 (9) | 0.0245 (8) | 0.0028 (7) | 0.0032 (7) | 0.0108 (7) |
C11 | 0.0371 (10) | 0.0266 (9) | 0.0260 (9) | −0.0001 (7) | 0.0091 (7) | 0.0070 (7) |
C12 | 0.0409 (11) | 0.0231 (9) | 0.0413 (11) | 0.0096 (8) | 0.0169 (9) | 0.0118 (8) |
C13 | 0.0364 (10) | 0.0333 (10) | 0.0414 (11) | 0.0150 (8) | 0.0092 (8) | 0.0201 (9) |
C14 | 0.0316 (9) | 0.0296 (9) | 0.0266 (8) | 0.0098 (7) | 0.0038 (7) | 0.0121 (7) |
C15 | 0.0225 (8) | 0.0233 (8) | 0.0227 (8) | 0.0081 (6) | 0.0039 (6) | 0.0117 (6) |
C16 | 0.0260 (9) | 0.0531 (12) | 0.0292 (9) | 0.0036 (8) | 0.0057 (7) | 0.0262 (9) |
C17 | 0.0238 (9) | 0.0654 (15) | 0.0401 (11) | −0.0027 (9) | 0.0013 (8) | 0.0312 (11) |
C18 | 0.0286 (9) | 0.0472 (11) | 0.0289 (9) | 0.0068 (8) | −0.0010 (7) | 0.0179 (8) |
C19 | 0.0370 (10) | 0.0330 (9) | 0.0218 (8) | 0.0109 (8) | 0.0069 (7) | 0.0151 (7) |
C20 | 0.0272 (8) | 0.0239 (8) | 0.0264 (8) | 0.0071 (6) | 0.0079 (7) | 0.0133 (7) |
I—C4 | 2.104 (2) | C10—C11 | 1.391 (3) |
I—O2i | 3.124 (1) | C10—H10 | 0.9300 |
S—O2 | 1.497 (1) | C11—C12 | 1.387 (3) |
S—C1 | 1.768 (2) | C11—H11 | 0.9300 |
S—C15 | 1.799 (2) | C12—C13 | 1.386 (3) |
O1—C8 | 1.377 (2) | C12—H12 | 0.9300 |
O1—C7 | 1.378 (2) | C13—C14 | 1.389 (3) |
C1—C8 | 1.367 (2) | C13—H13 | 0.9300 |
C1—C2 | 1.447 (2) | C14—H14 | 0.9300 |
C2—C7 | 1.394 (2) | C15—C16 | 1.388 (2) |
C2—C3 | 1.397 (2) | C15—C20 | 1.392 (2) |
C3—C4 | 1.388 (2) | C16—C17 | 1.387 (3) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.404 (2) | C17—C18 | 1.386 (3) |
C5—C6 | 1.389 (3) | C17—H17 | 0.9300 |
C5—H5 | 0.9300 | C18—C19 | 1.382 (3) |
C6—C7 | 1.387 (2) | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—C20 | 1.389 (3) |
C8—C9 | 1.463 (2) | C19—H19 | 0.9300 |
C9—C14 | 1.397 (2) | C20—H20 | 0.9300 |
C9—C10 | 1.401 (2) | ||
C4—I—O2i | 165.84 (5) | C11—C10—H10 | 120.4 |
O2—S—C1 | 107.63 (7) | C9—C10—H10 | 120.4 |
O2—S—C15 | 106.00 (8) | C12—C11—C10 | 120.66 (17) |
C1—S—C15 | 100.57 (8) | C12—C11—H11 | 119.7 |
C8—O1—C7 | 106.38 (12) | C10—C11—H11 | 119.7 |
C8—C1—C2 | 107.02 (14) | C13—C12—C11 | 120.13 (17) |
C8—C1—S | 123.64 (13) | C13—C12—H12 | 119.9 |
C2—C1—S | 128.38 (12) | C11—C12—H12 | 119.9 |
C7—C2—C3 | 119.26 (15) | C12—C13—C14 | 119.94 (18) |
C7—C2—C1 | 104.91 (14) | C12—C13—H13 | 120.0 |
C3—C2—C1 | 135.83 (15) | C14—C13—H13 | 120.0 |
C4—C3—C2 | 117.47 (15) | C13—C14—C9 | 120.11 (17) |
C4—C3—H3 | 121.3 | C13—C14—H14 | 119.9 |
C2—C3—H3 | 121.3 | C9—C14—H14 | 119.9 |
C3—C4—C5 | 122.37 (16) | C16—C15—C20 | 120.95 (16) |
C3—C4—I | 118.65 (12) | C16—C15—S | 123.40 (13) |
C5—C4—I | 118.96 (12) | C20—C15—S | 115.34 (13) |
C6—C5—C4 | 120.55 (15) | C17—C16—C15 | 119.05 (17) |
C6—C5—H5 | 119.7 | C17—C16—H16 | 120.5 |
C4—C5—H5 | 119.7 | C15—C16—H16 | 120.5 |
C7—C6—C5 | 116.34 (16) | C18—C17—C16 | 120.50 (18) |
C7—C6—H6 | 121.8 | C18—C17—H17 | 119.8 |
C5—C6—H6 | 121.8 | C16—C17—H17 | 119.8 |
O1—C7—C6 | 125.17 (15) | C19—C18—C17 | 120.03 (18) |
O1—C7—C2 | 110.82 (14) | C19—C18—H18 | 120.0 |
C6—C7—C2 | 124.00 (16) | C17—C18—H18 | 120.0 |
C1—C8—O1 | 110.87 (14) | C18—C19—C20 | 120.30 (16) |
C1—C8—C9 | 133.30 (15) | C18—C19—H19 | 119.8 |
O1—C8—C9 | 115.81 (14) | C20—C19—H19 | 119.8 |
C14—C9—C10 | 119.94 (16) | C19—C20—C15 | 119.15 (16) |
C14—C9—C8 | 120.26 (15) | C19—C20—H20 | 120.4 |
C10—C9—C8 | 119.80 (15) | C15—C20—H20 | 120.4 |
C11—C10—C9 | 119.19 (17) | ||
O2—S—C1—C8 | −134.10 (15) | C7—O1—C8—C1 | −0.06 (18) |
C15—S—C1—C8 | 115.21 (15) | C7—O1—C8—C9 | −178.86 (14) |
O2—S—C1—C2 | 33.18 (17) | C1—C8—C9—C14 | −39.3 (3) |
C15—S—C1—C2 | −77.52 (16) | O1—C8—C9—C14 | 139.16 (16) |
C8—C1—C2—C7 | 0.54 (18) | C1—C8—C9—C10 | 140.9 (2) |
S—C1—C2—C7 | −168.40 (13) | O1—C8—C9—C10 | −40.7 (2) |
C8—C1—C2—C3 | −179.78 (19) | C14—C9—C10—C11 | 1.5 (3) |
S—C1—C2—C3 | 11.3 (3) | C8—C9—C10—C11 | −178.63 (16) |
C7—C2—C3—C4 | −0.6 (2) | C9—C10—C11—C12 | −1.6 (3) |
C1—C2—C3—C4 | 179.73 (18) | C10—C11—C12—C13 | 0.7 (3) |
C2—C3—C4—C5 | 0.0 (2) | C11—C12—C13—C14 | 0.2 (3) |
C2—C3—C4—I | 178.71 (12) | C12—C13—C14—C9 | −0.2 (3) |
C3—C4—C5—C6 | 0.6 (3) | C10—C9—C14—C13 | −0.7 (3) |
I—C4—C5—C6 | −178.10 (13) | C8—C9—C14—C13 | 179.52 (17) |
C4—C5—C6—C7 | −0.5 (3) | O2—S—C15—C16 | −135.76 (16) |
C8—O1—C7—C6 | 179.37 (17) | C1—S—C15—C16 | −23.80 (17) |
C8—O1—C7—C2 | 0.42 (18) | O2—S—C15—C20 | 50.62 (14) |
C5—C6—C7—O1 | −178.91 (16) | C1—S—C15—C20 | 162.58 (13) |
C5—C6—C7—C2 | −0.1 (3) | C20—C15—C16—C17 | 0.3 (3) |
C3—C2—C7—O1 | 179.66 (14) | S—C15—C16—C17 | −172.99 (17) |
C1—C2—C7—O1 | −0.59 (18) | C15—C16—C17—C18 | 0.5 (3) |
C3—C2—C7—C6 | 0.7 (3) | C16—C17—C18—C19 | −0.8 (4) |
C1—C2—C7—C6 | −179.56 (16) | C17—C18—C19—C20 | 0.4 (3) |
C2—C1—C8—O1 | −0.30 (19) | C18—C19—C20—C15 | 0.4 (3) |
S—C1—C8—O1 | 169.29 (11) | C16—C15—C20—C19 | −0.7 (3) |
C2—C1—C8—C9 | 178.21 (17) | S—C15—C20—C19 | 173.06 (13) |
S—C1—C8—C9 | −12.2 (3) |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O2ii | 0.93 | 2.53 | 3.438 (2) | 165 |
C19—H19···O1iii | 0.93 | 2.59 | 3.483 (2) | 162 |
C20—H20···O2iv | 0.93 | 2.53 | 3.412 (2) | 159 |
Symmetry codes: (ii) −x, −y, −z; (iii) x, y, z+1; (iv) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H13IO2S |
Mr | 444.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 9.3544 (4), 9.7565 (5), 10.2808 (5) |
α, β, γ (°) | 113.381 (1), 92.640 (1), 98.047 (1) |
V (Å3) | 847.42 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.02 |
Crystal size (mm) | 0.40 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.467, 0.665 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7217, 3616, 3503 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.017, 0.044, 1.07 |
No. of reflections | 3616 |
No. of parameters | 217 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (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).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O2i | 0.93 | 2.53 | 3.438 (2) | 164.8 |
C19—H19···O1ii | 0.93 | 2.59 | 3.483 (2) | 161.6 |
C20—H20···O2iii | 0.93 | 2.53 | 3.412 (2) | 158.6 |
Symmetry codes: (i) −x, −y, −z; (ii) x, y, z+1; (iii) −x, −y, −z+1. |
This work is related to our communications on the synthesis and structures of 5-iodo-1-benzofuran analogues, viz. 5-iodo-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007a) and 5-iodo-2-methyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2007b). We present the crystal structure of the title compound (I), 5-iodo-2-phenyl-3-phenylsulfinyl-1-benzofuran (Fig. 1).
The benzofuran unit is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle in (I) formed by the planes of the benzofuran and 2-phenyl rings is 40.47 (5)°, and the phenyl ring (C15-C20) with 83.84 (5)° lies toward the benzofuran plane. The crystal packing (Fig. 2) is stabilized by non-classical intermolecular C–H···O interactions; the first between an H atom of the 2-phenyl ring and the oxygen of the S═O unit, with a C10–H10···O2i, the second between a phenyl H atom of the phenylsulfinyl substituent and the furan O atom, with a C19–H19···O1ii, the third between a phenyl H atom of the phenylsulfinyl substituent and the oxygen of the S═O unit, with a C20–H20···O2iii, respectively (Table 1 and Fig. 2; symmetry code as in Fig. 2). The molecular packing (Fig. 2) is further stabilized by an I···O halogen bond (Politzer et al., 2007) between the iodine atom and the oxygen of neighbouring S═O unit, with an I···Oiv (Symmetry code as in Fig. 2). The observed I···O separation of 3.124 (1) Å and the nearly linear C–I···O angle of 165.84 (5)° are typical for such halogen bonds. A search of Cambridge Structural Database (version 5.28; Allen, 2002) revealed 39 compounds with C–I···O═S contact distances equal to or less than 3.3 Å.