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

In the title compound, C(15)H(10)FIO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-iodo-phenyl ring is rotated out of the benzofuran plane by a dihedral angle of 39.4 (1)°. The crystal structure is stabilized by an inter-molecular C-H⋯O hydrogen bond and an I⋯O halogen bond [3.055 (2) Å]. The crystal structure also exhibits an inter-molecular C-H⋯π inter-action between the methyl H atom and the 4-iodo-phenyl ring of an adjacent benzofuran mol-ecule, and aromatic π-π inter-actions between the benzene rings of neighbouring benzofuran systems [centroid-centroid distance = 3.558 (3) Å].

Related literature

For the crystal structures of similar 2-(4-iodo­phen­yl)-3-methyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2008a ▶,b ▶). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C15H10FIO2S

M = 400.19

Triclinic,

a = 8.8989 (5) Å

b = 9.2370 (5) Å

c = 10.3357 (5) Å

α = 105.579 (1)°

β = 115.302 (1)°

γ = 101.671 (1)°

V = 689.08 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.48 mm−1

T = 273 K

0.25 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶)) T min = 0.650, T max = 0.784

5972 measured reflections

2957 independent reflections

2689 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.055

S = 1.09

2957 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.55 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/S1600536809030992/vm2001sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030992/vm2001Isup2.hkl

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

C15H10FIO2S	Z = 2
Mr = 400.19	F(000) = 388
Triclinic, P1	Dx = 1.929 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8989 (5) Å	Cell parameters from 4508 reflections
b = 9.2370 (5) Å	θ = 2.4–27.4°
c = 10.3357 (5) Å	µ = 2.48 mm−1
α = 105.579 (1)°	T = 273 K
β = 115.302 (1)°	Block, colorless
γ = 101.671 (1)°	0.25 × 0.15 × 0.10 mm
V = 689.08 (6) Å3

Bruker SMART CCD diffractometer	2957 independent reflections
Radiation source: fine-focus sealed tube	2689 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.4°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2000))	k = −11→11
Tmin = 0.650, Tmax = 0.784	l = −13→13
5972 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)] = 0.022	Hydrogen site location: difference Fourier map
wR(F2) = 0.055	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0248P)2 + 0.3594P] where P = (Fo2 + 2Fc2)/3
2957 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.55 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	0.87629 (2)	0.09755 (2)	−0.19147 (2)	0.03012 (7)
S	0.81950 (8)	0.77048 (7)	0.37848 (7)	0.02442 (13)
F	0.2583 (2)	0.7621 (2)	0.5294 (2)	0.0428 (4)
O1	0.4384 (2)	0.3431 (2)	0.1980 (2)	0.0233 (4)
O2	0.8909 (3)	0.8594 (2)	0.5482 (2)	0.0356 (4)
C1	0.6269 (3)	0.6020 (3)	0.3101 (3)	0.0219 (5)
C2	0.4906 (3)	0.5987 (3)	0.3510 (3)	0.0222 (5)
C3	0.4518 (3)	0.7126 (3)	0.4387 (3)	0.0264 (5)
H3	0.5242	0.8214	0.4904	0.032*
C4	0.3009 (4)	0.6553 (3)	0.4443 (3)	0.0292 (6)
C5	0.1882 (4)	0.4941 (4)	0.3707 (3)	0.0310 (6)
H5	0.0871	0.4634	0.3783	0.037*
C6	0.2275 (3)	0.3798 (3)	0.2861 (3)	0.0269 (5)
H6	0.1562	0.2709	0.2367	0.032*
C7	0.3788 (3)	0.4369 (3)	0.2791 (3)	0.0226 (5)
C8	0.5907 (3)	0.4480 (3)	0.2194 (3)	0.0220 (5)
C9	0.6706 (3)	0.3730 (3)	0.1356 (3)	0.0215 (5)
C10	0.6734 (3)	0.2185 (3)	0.1215 (3)	0.0254 (5)
H10	0.6323	0.1671	0.1724	0.030*
C11	0.7365 (3)	0.1415 (3)	0.0331 (3)	0.0262 (5)
H11	0.7377	0.0389	0.0242	0.031*
C12	0.7985 (3)	0.2194 (3)	−0.0429 (3)	0.0225 (5)
C13	0.7989 (3)	0.3733 (3)	−0.0283 (3)	0.0225 (5)
H13	0.8410	0.4247	−0.0786	0.027*
C14	0.7364 (3)	0.4501 (3)	0.0616 (3)	0.0225 (5)
H14	0.7384	0.5539	0.0725	0.027*
C15	0.7072 (4)	0.8817 (3)	0.2787 (3)	0.0356 (6)
H15A	0.6214	0.8998	0.3076	0.053*
H15B	0.6475	0.8212	0.1679	0.053*
H15C	0.7929	0.9835	0.3071	0.053*

	U11	U22	U33	U12	U13	U23
I	0.03872 (11)	0.03141 (10)	0.02933 (10)	0.01738 (8)	0.02328 (8)	0.01132 (8)
S	0.0221 (3)	0.0233 (3)	0.0206 (3)	0.0048 (2)	0.0092 (3)	0.0043 (2)
F	0.0485 (11)	0.0531 (11)	0.0389 (10)	0.0314 (9)	0.0292 (9)	0.0139 (8)
O1	0.0238 (9)	0.0208 (8)	0.0252 (9)	0.0074 (7)	0.0141 (7)	0.0070 (7)
O2	0.0340 (11)	0.0350 (11)	0.0230 (9)	0.0030 (9)	0.0127 (8)	0.0015 (8)
C1	0.0206 (12)	0.0228 (12)	0.0181 (11)	0.0074 (10)	0.0076 (10)	0.0065 (10)
C2	0.0212 (12)	0.0263 (12)	0.0165 (11)	0.0101 (10)	0.0071 (10)	0.0084 (10)
C3	0.0302 (13)	0.0279 (13)	0.0194 (12)	0.0138 (11)	0.0112 (11)	0.0073 (10)
C4	0.0329 (14)	0.0414 (15)	0.0209 (12)	0.0251 (13)	0.0149 (11)	0.0126 (12)
C5	0.0256 (13)	0.0466 (16)	0.0299 (14)	0.0187 (12)	0.0161 (12)	0.0206 (13)
C6	0.0239 (13)	0.0313 (14)	0.0264 (13)	0.0110 (11)	0.0117 (11)	0.0140 (11)
C7	0.0249 (12)	0.0263 (12)	0.0185 (11)	0.0132 (10)	0.0102 (10)	0.0100 (10)
C8	0.0225 (12)	0.0239 (12)	0.0188 (11)	0.0076 (10)	0.0096 (10)	0.0097 (10)
C9	0.0195 (12)	0.0198 (11)	0.0188 (11)	0.0058 (9)	0.0074 (10)	0.0042 (9)
C10	0.0287 (13)	0.0248 (12)	0.0257 (13)	0.0093 (11)	0.0150 (11)	0.0128 (11)
C11	0.0317 (14)	0.0218 (12)	0.0289 (13)	0.0117 (11)	0.0169 (11)	0.0113 (11)
C12	0.0215 (12)	0.0238 (12)	0.0190 (11)	0.0074 (10)	0.0104 (10)	0.0046 (10)
C13	0.0205 (12)	0.0253 (12)	0.0183 (11)	0.0050 (10)	0.0090 (10)	0.0079 (10)
C14	0.0214 (12)	0.0203 (11)	0.0206 (12)	0.0064 (10)	0.0076 (10)	0.0072 (10)
C15	0.0327 (15)	0.0257 (14)	0.0391 (16)	0.0067 (12)	0.0117 (13)	0.0141 (12)

I—C12	2.098 (2)	C6—C7	1.383 (3)
I—O2i	3.055 (2)	C6—H6	0.9300
S—O2	1.489 (2)	C8—C9	1.463 (3)
S—C1	1.776 (2)	C9—C14	1.394 (3)
S—C15	1.794 (3)	C9—C10	1.402 (3)
F—C4	1.364 (3)	C10—C11	1.381 (4)
O1—C7	1.382 (3)	C10—H10	0.9300
O1—C8	1.386 (3)	C11—C12	1.398 (3)
C1—C8	1.359 (3)	C11—H11	0.9300
C1—C2	1.443 (3)	C12—C13	1.387 (3)
C2—C7	1.395 (3)	C13—C14	1.387 (3)
C2—C3	1.396 (3)	C13—H13	0.9300
C3—C4	1.373 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.391 (4)	C15—H15B	0.9600
C5—C6	1.384 (4)	C15—H15C	0.9600
C5—H5	0.9300
C12—I—O2i	165.26 (8)	C1—C8—C9	134.3 (2)
O2—S—C1	106.61 (11)	O1—C8—C9	114.9 (2)
O2—S—C15	107.29 (13)	C14—C9—C10	119.0 (2)
C1—S—C15	97.37 (12)	C14—C9—C8	120.6 (2)
C7—O1—C8	106.13 (18)	C10—C9—C8	120.3 (2)
C8—C1—C2	107.4 (2)	C11—C10—C9	121.0 (2)
C8—C1—S	125.10 (19)	C11—C10—H10	119.5
C2—C1—S	127.23 (18)	C9—C10—H10	119.5
C7—C2—C3	119.1 (2)	C10—C11—C12	119.2 (2)
C7—C2—C1	105.1 (2)	C10—C11—H11	120.4
C3—C2—C1	135.9 (2)	C12—C11—H11	120.4
C4—C3—C2	116.3 (2)	C13—C12—C11	120.5 (2)
C4—C3—H3	121.9	C13—C12—I	119.62 (17)
C2—C3—H3	121.9	C11—C12—I	119.79 (18)
F—C4—C3	118.3 (2)	C14—C13—C12	119.9 (2)
F—C4—C5	117.1 (2)	C14—C13—H13	120.1
C3—C4—C5	124.5 (2)	C12—C13—H13	120.1
C6—C5—C4	119.6 (2)	C13—C14—C9	120.5 (2)
C6—C5—H5	120.2	C13—C14—H14	119.8
C4—C5—H5	120.2	C9—C14—H14	119.8
C7—C6—C5	116.2 (2)	S—C15—H15A	109.5
C7—C6—H6	121.9	S—C15—H15B	109.5
C5—C6—H6	121.9	H15A—C15—H15B	109.5
O1—C7—C6	125.1 (2)	S—C15—H15C	109.5
O1—C7—C2	110.6 (2)	H15A—C15—H15C	109.5
C6—C7—C2	124.3 (2)	H15B—C15—H15C	109.5
C1—C8—O1	110.7 (2)
O2—S—C1—C8	−132.7 (2)	C2—C1—C8—O1	0.0 (3)
C15—S—C1—C8	116.8 (2)	S—C1—C8—O1	174.65 (16)
O2—S—C1—C2	40.9 (2)	C2—C1—C8—C9	176.3 (3)
C15—S—C1—C2	−69.7 (2)	S—C1—C8—C9	−9.1 (4)
C8—C1—C2—C7	0.0 (3)	C7—O1—C8—C1	0.0 (3)
S—C1—C2—C7	−174.51 (18)	C7—O1—C8—C9	−177.1 (2)
C8—C1—C2—C3	−179.9 (3)	C1—C8—C9—C14	−37.3 (4)
S—C1—C2—C3	5.6 (4)	O1—C8—C9—C14	138.8 (2)
C7—C2—C3—C4	−1.4 (3)	C1—C8—C9—C10	146.1 (3)
C1—C2—C3—C4	178.5 (3)	O1—C8—C9—C10	−37.8 (3)
C2—C3—C4—F	179.6 (2)	C14—C9—C10—C11	−1.4 (4)
C2—C3—C4—C5	0.5 (4)	C8—C9—C10—C11	175.2 (2)
F—C4—C5—C6	−178.4 (2)	C9—C10—C11—C12	0.1 (4)
C3—C4—C5—C6	0.7 (4)	C10—C11—C12—C13	0.8 (4)
C4—C5—C6—C7	−1.0 (4)	C10—C11—C12—I	−175.29 (19)
C8—O1—C7—C6	178.8 (2)	O2i—I—C12—C13	−117.3 (3)
C8—O1—C7—C2	0.0 (2)	O2i—I—C12—C11	58.8 (4)
C5—C6—C7—O1	−178.5 (2)	C11—C12—C13—C14	−0.4 (4)
C5—C6—C7—C2	0.1 (4)	I—C12—C13—C14	175.70 (18)
C3—C2—C7—O1	179.9 (2)	C12—C13—C14—C9	−1.0 (4)
C1—C2—C7—O1	0.0 (3)	C10—C9—C14—C13	1.8 (4)
C3—C2—C7—C6	1.1 (4)	C8—C9—C14—C13	−174.8 (2)
C1—C2—C7—C6	−178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···O2ii	0.96	2.42	3.238 (3)	143
C15—H15B···Cg3iii	0.96	2.91	3.554 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯O2i	0.96	2.42	3.238 (3)	143
C15—H15B⋯Cg3ii	0.96	2.91	3.554 (3)	126

Symmetry codes: (i) ; (ii) . Cg3 is the centroid of the C9–C14 benzene ring.