5-Iodo-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

In the title compound, C(20)H(13)IO(2)S, the O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment; the phenyl ring is almost perpendicular to this plane [83.84 (5)°]. The phenyl ring in the 2-position is rotated out of the benzofuran plane, making a dihedral angle of 40.47 (5)°. The crystal structure is stabilized by non-classical inter-molecular C-H⋯O inter-actions, and by an I⋯O halogen bond of 3.124 (1) Å [C-I⋯O = 165.84 (5)°].

Related literature

For the crystal structures of similar 5-iodo-1-benzofuran derivatives, see: Choi et al. (2007a ▶,b ▶). For a review of halogen inter­actions, see: Politzer et al. (2007 ▶). The Cambridge Structural Database (version 5.28; Allen et al., 2002 ▶) has 39 compounds with C–I⋯O=S contact distances less than or equal to 3.3 Å.

Experimental

Crystal data

C20H13IO2S

M = 444.26

Triclinic,

a = 9.3544 (4) Å

b = 9.7565 (5) Å

c = 10.2808 (5) Å

α = 113.381 (1)°

β = 92.640 (1)°

γ = 98.047 (1)°

V = 847.42 (7) Å3

Z = 2

Mo Kα radiation

μ = 2.02 mm−1

T = 273 K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.467, T max = 0.665

7217 measured reflections

3616 independent reflections

3503 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.044

S = 1.07

3616 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.66 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024556/ng2605sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024556/ng2605Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2i	0.93	2.53	3.438 (2)	165
C19—H19⋯O1ii	0.93	2.59	3.483 (2)	162
C20—H20⋯O2iii	0.93	2.53	3.412 (2)	159

Symmetry codes: (i) ; (ii) ; (iii) .