3-Ethyl-sulfinyl-2-(4-iodo-phen-yl)-5-methyl-1-benzofuran.

In the title compound, C(17)H(15)IO(2)S, the 4-iodo-phenyl ring makes a dihedral angle of 35.39 (8)° with the plane of the benzofuran fragment. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O and C-H⋯π inter-actions, and an I⋯O contact [3.378 (2) Å]. The crystal structure also exhibits aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.495 (3) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the structures of related 3-ethyl­sulfinyl-5-halo-2-(4-halophen­yl)-1-benzofuran derivatives, see: Choi et al. (2010 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H15IO2S

M = 410.25

Monoclinic,

a = 10.1034 (3) Å

b = 13.1942 (4) Å

c = 11.9933 (3) Å

β = 92.634 (1)°

V = 1597.09 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.14 mm−1

T = 173 K

0.32 × 0.27 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.551, T max = 0.834

15129 measured reflections

3667 independent reflections

3366 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.069

S = 1.07

3667 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.96 e Å−3

Δρmin = −0.69 e Å−3

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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026620/bg2357sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026620/bg2357Isup2.hkl

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

C17H15IO2S	F(000) = 808
Mr = 410.25	Dx = 1.706 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9921 reflections
a = 10.1034 (3) Å	θ = 2.3–27.5°
b = 13.1942 (4) Å	µ = 2.14 mm−1
c = 11.9933 (3) Å	T = 173 K
β = 92.634 (1)°	Block, colourless
V = 1597.09 (8) Å3	0.32 × 0.27 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3667 independent reflections
Radiation source: rotating anode	3366 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.025
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.3°
φ and ω scans	h = −8→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −17→10
Tmin = 0.551, Tmax = 0.834	l = −15→15
15129 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)] = 0.026	Hydrogen site location: difference Fourier map
wR(F2) = 0.069	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0328P)2 + 1.5593P] where P = (Fo2 + 2Fc2)/3
3667 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.96 e Å−3
0 restraints	Δρmin = −0.69 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	0.491732 (16)	0.129285 (13)	1.209790 (12)	0.03433 (7)
S	0.44476 (6)	0.12571 (4)	0.57565 (5)	0.02928 (13)
O2	0.5466 (2)	0.12728 (14)	0.48973 (19)	0.0451 (5)
O1	0.36148 (16)	0.39156 (12)	0.71054 (13)	0.0269 (3)
C1	0.4080 (2)	0.25304 (17)	0.60955 (18)	0.0254 (4)
C2	0.3800 (2)	0.33516 (18)	0.53236 (19)	0.0253 (4)
C3	0.3795 (2)	0.34768 (18)	0.41673 (19)	0.0281 (5)
H3	0.3964	0.2931	0.3704	0.034*
C4	0.3531 (2)	0.44313 (19)	0.3722 (2)	0.0292 (5)
C5	0.3273 (2)	0.52457 (18)	0.4432 (2)	0.0300 (5)
H5	0.3108	0.5881	0.4120	0.036*
C6	0.3253 (2)	0.51387 (18)	0.5580 (2)	0.0290 (5)
H6	0.3068	0.5680	0.6045	0.035*
C7	0.3525 (2)	0.41812 (17)	0.59933 (18)	0.0253 (4)
C8	0.3968 (2)	0.29066 (17)	0.71460 (18)	0.0255 (4)
C9	0.4144 (2)	0.24931 (17)	0.82760 (18)	0.0261 (4)
C10	0.5115 (2)	0.1770 (2)	0.85308 (19)	0.0309 (5)
H10	0.5633	0.1525	0.7969	0.037*
C11	0.5319 (3)	0.14090 (19)	0.9612 (2)	0.0315 (5)
H11	0.5966	0.0923	0.9775	0.038*
C12	0.4547 (2)	0.17826 (18)	1.04487 (18)	0.0276 (5)
C13	0.3559 (2)	0.24893 (18)	1.02076 (19)	0.0288 (5)
H13	0.3034	0.2725	1.0769	0.035*
C14	0.3359 (2)	0.28432 (18)	0.91224 (19)	0.0283 (5)
H14	0.2697	0.3317	0.8959	0.034*
C15	0.3528 (3)	0.4598 (2)	0.2475 (2)	0.0384 (6)
H15A	0.4124	0.4127	0.2151	0.058*
H15B	0.3810	0.5278	0.2326	0.058*
H15C	0.2649	0.4496	0.2156	0.058*
C16	0.2900 (3)	0.0929 (2)	0.5052 (2)	0.0372 (6)
H16A	0.2704	0.1419	0.4465	0.045*
H16B	0.2984	0.0270	0.4705	0.045*
C17	0.1766 (3)	0.0902 (2)	0.5821 (3)	0.0486 (7)
H17A	0.1975	0.0446	0.6428	0.073*
H17B	0.0981	0.0673	0.5417	0.073*
H17C	0.1620	0.1569	0.6109	0.073*

	U11	U22	U33	U12	U13	U23
I	0.03738 (11)	0.04108 (12)	0.02435 (9)	0.00488 (7)	−0.00062 (7)	0.00094 (6)
S	0.0299 (3)	0.0259 (3)	0.0322 (3)	0.0037 (2)	0.0021 (2)	−0.0051 (2)
O2	0.0406 (11)	0.0417 (11)	0.0547 (13)	0.0043 (8)	0.0192 (10)	−0.0043 (9)
O1	0.0306 (8)	0.0241 (8)	0.0258 (8)	0.0025 (6)	−0.0021 (6)	−0.0040 (6)
C1	0.0272 (11)	0.0226 (11)	0.0264 (10)	0.0002 (8)	0.0006 (8)	−0.0023 (8)
C2	0.0228 (10)	0.0249 (11)	0.0283 (11)	−0.0021 (9)	0.0007 (8)	−0.0019 (9)
C3	0.0284 (11)	0.0286 (11)	0.0275 (11)	−0.0032 (9)	0.0035 (9)	−0.0028 (9)
C4	0.0242 (11)	0.0340 (12)	0.0294 (11)	−0.0053 (9)	0.0023 (9)	0.0032 (9)
C5	0.0259 (11)	0.0265 (11)	0.0373 (12)	−0.0018 (9)	−0.0010 (9)	0.0042 (9)
C6	0.0267 (11)	0.0257 (11)	0.0344 (12)	0.0002 (9)	−0.0014 (9)	−0.0040 (9)
C7	0.0235 (10)	0.0271 (11)	0.0253 (10)	−0.0013 (9)	−0.0010 (8)	−0.0028 (8)
C8	0.0243 (10)	0.0242 (11)	0.0278 (10)	0.0020 (8)	−0.0005 (8)	−0.0027 (8)
C9	0.0260 (11)	0.0277 (11)	0.0244 (10)	0.0001 (9)	−0.0017 (8)	−0.0032 (8)
C10	0.0283 (12)	0.0400 (14)	0.0244 (10)	0.0086 (10)	0.0020 (9)	−0.0033 (9)
C11	0.0288 (12)	0.0362 (13)	0.0290 (11)	0.0079 (10)	−0.0031 (9)	−0.0034 (9)
C12	0.0293 (11)	0.0298 (12)	0.0234 (10)	−0.0015 (9)	−0.0014 (9)	−0.0037 (9)
C13	0.0308 (12)	0.0295 (12)	0.0265 (11)	0.0034 (9)	0.0035 (9)	−0.0048 (9)
C14	0.0280 (11)	0.0258 (11)	0.0310 (11)	0.0049 (9)	−0.0002 (9)	−0.0032 (9)
C15	0.0434 (15)	0.0424 (15)	0.0298 (12)	−0.0048 (12)	0.0044 (10)	0.0068 (11)
C16	0.0397 (14)	0.0326 (13)	0.0392 (13)	−0.0019 (11)	−0.0007 (11)	−0.0048 (11)
C17	0.0383 (15)	0.0398 (15)	0.068 (2)	−0.0042 (12)	0.0118 (14)	−0.0039 (14)

I—C12	2.098 (2)	C9—C10	1.392 (3)
I—O2i	3.378 (2)	C9—C14	1.395 (3)
S—O2	1.490 (2)	C10—C11	1.388 (3)
S—C1	1.772 (2)	C10—H10	0.9300
S—C16	1.796 (3)	C11—C12	1.390 (3)
O1—C7	1.378 (3)	C11—H11	0.9300
O1—C8	1.379 (3)	C12—C13	1.386 (3)
C1—C8	1.364 (3)	C13—C14	1.389 (3)
C1—C2	1.445 (3)	C13—H13	0.9300
C2—C7	1.393 (3)	C14—H14	0.9300
C2—C3	1.396 (3)	C15—H15A	0.9600
C3—C4	1.389 (3)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.402 (3)	C16—C17	1.503 (4)
C4—C15	1.513 (3)	C16—H16A	0.9700
C5—C6	1.386 (3)	C16—H16B	0.9700
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.380 (3)	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C8—C9	1.464 (3)
C12—I—O2i	162.46 (7)	C11—C10—H10	119.6
O2—S—C1	107.71 (11)	C9—C10—H10	119.6
O2—S—C16	107.00 (13)	C10—C11—C12	119.3 (2)
C1—S—C16	98.58 (12)	C10—C11—H11	120.4
C7—O1—C8	106.57 (17)	C12—C11—H11	120.4
C8—C1—C2	107.27 (19)	C13—C12—C11	120.7 (2)
C8—C1—S	125.75 (18)	C13—C12—I	119.95 (16)
C2—C1—S	126.94 (17)	C11—C12—I	119.34 (18)
C7—C2—C3	119.2 (2)	C12—C13—C14	119.6 (2)
C7—C2—C1	104.97 (19)	C12—C13—H13	120.2
C3—C2—C1	135.8 (2)	C14—C13—H13	120.2
C4—C3—C2	118.7 (2)	C13—C14—C9	120.5 (2)
C4—C3—H3	120.6	C13—C14—H14	119.8
C2—C3—H3	120.6	C9—C14—H14	119.8
C3—C4—C5	120.0 (2)	C4—C15—H15A	109.5
C3—C4—C15	120.3 (2)	C4—C15—H15B	109.5
C5—C4—C15	119.8 (2)	H15A—C15—H15B	109.5
C6—C5—C4	122.4 (2)	C4—C15—H15C	109.5
C6—C5—H5	118.8	H15A—C15—H15C	109.5
C4—C5—H5	118.8	H15B—C15—H15C	109.5
C7—C6—C5	116.0 (2)	C17—C16—S	112.9 (2)
C7—C6—H6	122.0	C17—C16—H16A	109.0
C5—C6—H6	122.0	S—C16—H16A	109.0
O1—C7—C6	125.7 (2)	C17—C16—H16B	109.0
O1—C7—C2	110.6 (2)	S—C16—H16B	109.0
C6—C7—C2	123.6 (2)	H16A—C16—H16B	107.8
C1—C8—O1	110.56 (19)	C16—C17—H17A	109.5
C1—C8—C9	135.1 (2)	C16—C17—H17B	109.5
O1—C8—C9	114.37 (18)	H17A—C17—H17B	109.5
C10—C9—C14	119.0 (2)	C16—C17—H17C	109.5
C10—C9—C8	120.9 (2)	H17A—C17—H17C	109.5
C14—C9—C8	120.1 (2)	H17B—C17—H17C	109.5
C11—C10—C9	120.9 (2)
O2—S—C1—C8	−134.9 (2)	C2—C1—C8—O1	0.8 (3)
C16—S—C1—C8	114.1 (2)	S—C1—C8—O1	−177.22 (16)
O2—S—C1—C2	47.4 (2)	C2—C1—C8—C9	−178.6 (2)
C16—S—C1—C2	−63.6 (2)	S—C1—C8—C9	3.3 (4)
C8—C1—C2—C7	−0.4 (3)	C7—O1—C8—C1	−1.0 (2)
S—C1—C2—C7	177.68 (17)	C7—O1—C8—C9	178.56 (19)
C8—C1—C2—C3	177.1 (3)	C1—C8—C9—C10	34.9 (4)
S—C1—C2—C3	−4.8 (4)	O1—C8—C9—C10	−144.5 (2)
C7—C2—C3—C4	0.8 (3)	C1—C8—C9—C14	−146.9 (3)
C1—C2—C3—C4	−176.4 (2)	O1—C8—C9—C14	33.7 (3)
C2—C3—C4—C5	−0.2 (3)	C14—C9—C10—C11	−1.0 (4)
C2—C3—C4—C15	179.5 (2)	C8—C9—C10—C11	177.2 (2)
C3—C4—C5—C6	−0.7 (4)	C9—C10—C11—C12	−0.4 (4)
C15—C4—C5—C6	179.6 (2)	C10—C11—C12—C13	1.6 (4)
C4—C5—C6—C7	1.0 (3)	C10—C11—C12—I	−176.97 (19)
C8—O1—C7—C6	−176.9 (2)	C11—C12—C13—C14	−1.4 (4)
C8—O1—C7—C2	0.8 (2)	I—C12—C13—C14	177.17 (18)
C5—C6—C7—O1	177.0 (2)	C12—C13—C14—C9	0.0 (4)
C5—C6—C7—C2	−0.3 (3)	C10—C9—C14—C13	1.2 (4)
C3—C2—C7—O1	−178.3 (2)	C8—C9—C14—C13	−177.1 (2)
C1—C2—C7—O1	−0.3 (2)	O2—S—C16—C17	−179.0 (2)
C3—C2—C7—C6	−0.6 (4)	C1—S—C16—C17	−67.5 (2)
C1—C2—C7—C6	177.4 (2)

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O2ii	0.97	2.60	3.341 (3)	134
C11—H11···Cgiii	0.93	2.61	3.378 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O2i	0.97	2.60	3.341 (3)	134
C11—H11⋯Cgii	0.93	2.61	3.378 (3)	141

Symmetry codes: (i) ; (ii) .