3-Ethyl-sulfinyl-2-(3-fluoro-phen-yl)-5-iodo-7-methyl-1-benzofuran.

In the title compound, C(17)H(14)FIO(2)S, the 3-fluoro-phenyl ring makes a dihedral angle of 14.56 (5)° with the mean plane [r.m.s. deviation = 0.012 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked via pairs of I⋯O contacts [3.038 (2) Å], forming inversion dimers. In the 3-fluoro-phenyl ring, the F atom is disordered over two positions, with site-occupancy factors of 0.747 (3) and 0.253 (3).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2011 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H14FIO2S

M = 428.24

Triclinic,

a = 7.3338 (2) Å

b = 10.3610 (2) Å

c = 10.9799 (2) Å

α = 104.644 (1)°

β = 92.926 (1)°

γ = 102.035 (1)°

V = 784.71 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.19 mm−1

T = 173 K

0.35 × 0.29 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.556, T max = 0.746

14623 measured reflections

3918 independent reflections

3731 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.056

S = 1.08

3918 reflections

211 parameters

164 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.65 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 datablock(s) global, I. DOI: 10.1107/S1600536812039463/aa2071sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039463/aa2071Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039463/aa2071Isup3.cml

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

C17H14FIO2S	Z = 2
Mr = 428.24	F(000) = 420
Triclinic, P1	Dx = 1.812 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3338 (2) Å	Cell parameters from 9894 reflections
b = 10.3610 (2) Å	θ = 2.4–28.4°
c = 10.9799 (2) Å	µ = 2.19 mm−1
α = 104.644 (1)°	T = 173 K
β = 92.926 (1)°	Block, colourless
γ = 102.035 (1)°	0.35 × 0.29 × 0.24 mm
V = 784.71 (3) Å3

Bruker SMART APEXII CCD diffractometer	3918 independent reflections
Radiation source: rotating anode	3731 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.040
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.9°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.556, Tmax = 0.746	l = −14→14
14623 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) = 0.056	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0255P)2 + 0.2925P] where P = (Fo2 + 2Fc2)/3
3918 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.38 e Å−3
164 restraints	Δρmin = −0.65 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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	Occ. (<1)
I1	−0.011910 (18)	0.247792 (12)	−0.066263 (10)	0.03114 (5)
S1	0.27413 (7)	0.74595 (4)	0.42237 (4)	0.02679 (10)
O1	0.21349 (18)	0.39126 (13)	0.50876 (12)	0.0258 (3)
O2	0.1125 (2)	0.75365 (15)	0.33857 (14)	0.0336 (3)
C1	0.2420 (3)	0.57482 (18)	0.43099 (17)	0.0249 (3)
C2	0.1699 (3)	0.45433 (17)	0.32762 (17)	0.0238 (3)
C3	0.1203 (3)	0.42768 (18)	0.19759 (17)	0.0254 (3)
H3	0.1301	0.4996	0.1574	0.030*
C4	0.0563 (3)	0.29164 (18)	0.13005 (17)	0.0259 (3)
C5	0.0365 (3)	0.18389 (19)	0.18758 (19)	0.0280 (4)
H5	−0.0123	0.0925	0.1374	0.034*
C6	0.0869 (3)	0.20809 (18)	0.31681 (18)	0.0266 (4)
C7	0.1532 (3)	0.34487 (18)	0.38160 (17)	0.0238 (3)
C8	0.2659 (2)	0.53213 (18)	0.53774 (17)	0.0244 (3)
C9	0.0763 (3)	0.0950 (2)	0.3810 (2)	0.0353 (4)
H9A	0.2031	0.0840	0.4008	0.053*
H9B	0.0012	0.0092	0.3246	0.053*
H9C	0.0177	0.1180	0.4595	0.053*
C10	0.3342 (3)	0.5987 (2)	0.67072 (17)	0.0269 (4)
C11	0.2991 (3)	0.5240 (2)	0.76036 (19)	0.0317 (4)
H11	0.2285	0.4318	0.7353	0.038*
C12A	0.3681 (3)	0.5856 (3)	0.8849 (2)	0.0415 (5)	0.747 (3)
H12A	0.3459	0.5338	0.9449	0.050*	0.747 (3)
C12B	0.3681 (3)	0.5856 (3)	0.8849 (2)	0.0415 (5)	0.253 (3)
F1B	0.3501 (9)	0.5380 (6)	0.9793 (5)	0.0474 (16)	0.253 (3)
C13	0.4679 (3)	0.7192 (3)	0.9258 (2)	0.0439 (5)
H13	0.5145	0.7603	1.0123	0.053*
C14A	0.4974 (3)	0.7906 (2)	0.8370 (2)	0.0416 (5)	0.747 (3)
F1A	0.5917 (3)	0.91806 (18)	0.87743 (19)	0.0506 (6)	0.747 (3)
C14B	0.4974 (3)	0.7906 (2)	0.8370 (2)	0.0416 (5)	0.253 (3)
H14B	0.5641	0.8838	0.8639	0.050*	0.253 (3)
C15	0.4356 (3)	0.7346 (2)	0.7108 (2)	0.0341 (4)
H15	0.4613	0.7874	0.6519	0.041*
C16	0.4722 (3)	0.7479 (2)	0.3304 (2)	0.0340 (4)
H16A	0.5780	0.7295	0.3777	0.041*
H16B	0.4372	0.6750	0.2496	0.041*
C17	0.5320 (4)	0.8859 (2)	0.3032 (2)	0.0437 (5)
H17A	0.4294	0.9018	0.2524	0.066*
H17B	0.6424	0.8872	0.2565	0.066*
H17C	0.5631	0.9582	0.3833	0.066*

	U11	U22	U33	U12	U13	U23
I1	0.03983 (9)	0.02785 (8)	0.02227 (8)	0.00625 (6)	0.00093 (5)	0.00227 (5)
S1	0.0375 (2)	0.01877 (19)	0.0227 (2)	0.00580 (17)	0.00145 (18)	0.00388 (16)
O1	0.0304 (6)	0.0231 (6)	0.0247 (6)	0.0058 (5)	0.0021 (5)	0.0080 (5)
O2	0.0386 (8)	0.0319 (7)	0.0349 (7)	0.0133 (6)	0.0028 (6)	0.0134 (6)
C1	0.0292 (9)	0.0204 (8)	0.0238 (8)	0.0045 (7)	0.0021 (7)	0.0049 (6)
C2	0.0263 (8)	0.0201 (7)	0.0252 (8)	0.0060 (7)	0.0034 (7)	0.0060 (6)
C3	0.0303 (9)	0.0221 (8)	0.0241 (8)	0.0061 (7)	0.0019 (7)	0.0069 (7)
C4	0.0295 (9)	0.0251 (8)	0.0214 (8)	0.0065 (7)	0.0017 (7)	0.0034 (7)
C5	0.0313 (9)	0.0209 (8)	0.0294 (9)	0.0042 (7)	0.0035 (7)	0.0038 (7)
C6	0.0299 (9)	0.0211 (8)	0.0300 (9)	0.0060 (7)	0.0054 (7)	0.0083 (7)
C7	0.0254 (8)	0.0241 (8)	0.0228 (8)	0.0068 (7)	0.0029 (7)	0.0071 (7)
C8	0.0240 (8)	0.0235 (8)	0.0257 (8)	0.0052 (7)	0.0030 (7)	0.0066 (7)
C9	0.0505 (12)	0.0216 (8)	0.0347 (10)	0.0063 (8)	0.0062 (9)	0.0107 (8)
C10	0.0244 (8)	0.0345 (9)	0.0224 (8)	0.0097 (7)	0.0020 (7)	0.0062 (7)
C11	0.0277 (9)	0.0411 (11)	0.0279 (9)	0.0099 (8)	0.0040 (8)	0.0104 (8)
C12A	0.0369 (11)	0.0653 (15)	0.0250 (10)	0.0162 (11)	0.0023 (8)	0.0138 (10)
C12B	0.0369 (11)	0.0653 (15)	0.0250 (10)	0.0162 (11)	0.0023 (8)	0.0138 (10)
F1B	0.060 (3)	0.054 (3)	0.032 (3)	0.006 (3)	0.003 (2)	0.025 (2)
C13	0.0360 (11)	0.0660 (15)	0.0231 (10)	0.0139 (11)	−0.0038 (9)	0.0001 (9)
C14A	0.0360 (11)	0.0438 (12)	0.0362 (12)	0.0075 (10)	−0.0033 (9)	−0.0025 (9)
F1A	0.0606 (13)	0.0339 (9)	0.0430 (11)	−0.0028 (9)	−0.0106 (9)	−0.0012 (8)
C14B	0.0360 (11)	0.0438 (12)	0.0362 (12)	0.0075 (10)	−0.0033 (9)	−0.0025 (9)
C15	0.0345 (10)	0.0348 (10)	0.0290 (10)	0.0050 (8)	−0.0013 (8)	0.0051 (8)
C16	0.0350 (10)	0.0298 (9)	0.0362 (11)	0.0048 (8)	0.0048 (9)	0.0091 (8)
C17	0.0499 (13)	0.0345 (11)	0.0424 (12)	−0.0039 (10)	0.0055 (10)	0.0134 (9)

I1—C4	2.0982 (18)	C9—H9B	0.9800
I1—O2i	3.0384 (15)	C9—H9C	0.9800
S1—O2	1.4908 (15)	C10—C15	1.396 (3)
S1—C1	1.7666 (18)	C10—C11	1.401 (3)
S1—C16	1.811 (2)	C11—C12A	1.373 (3)
O1—C7	1.373 (2)	C11—H11	0.9500
O1—C8	1.378 (2)	C12A—C13	1.372 (4)
C1—C8	1.369 (2)	C12A—H12A	0.9500
C1—C2	1.440 (3)	C13—C14A	1.366 (4)
C2—C7	1.393 (2)	C13—H13	0.9500
C2—C3	1.397 (3)	C14A—F1A	1.308 (3)
C3—C4	1.385 (2)	C14A—C15	1.371 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.402 (3)	C16—C17	1.515 (3)
C5—C6	1.393 (3)	C16—H16A	0.9900
C5—H5	0.9500	C16—H16B	0.9900
C6—C7	1.385 (3)	C17—H17A	0.9800
C6—C9	1.504 (2)	C17—H17B	0.9800
C8—C10	1.459 (3)	C17—H17C	0.9800
C9—H9A	0.9800
C4—I1—O2i	168.17 (6)	H9A—C9—H9C	109.5
O2—S1—C1	107.75 (9)	H9B—C9—H9C	109.5
O2—S1—C16	106.73 (9)	C15—C10—C11	119.02 (18)
C1—S1—C16	97.34 (9)	C15—C10—C8	121.67 (17)
C7—O1—C8	107.04 (13)	C11—C10—C8	119.31 (18)
C8—C1—C2	107.39 (15)	C12A—C11—C10	119.2 (2)
C8—C1—S1	126.73 (14)	C12A—C11—H11	120.4
C2—C1—S1	125.69 (13)	C10—C11—H11	120.4
C7—C2—C3	119.11 (16)	C13—C12A—C11	122.5 (2)
C7—C2—C1	105.07 (15)	C13—C12A—H12A	118.8
C3—C2—C1	135.82 (16)	C11—C12A—H12A	118.8
C4—C3—C2	116.93 (16)	C14A—C13—C12A	117.2 (2)
C4—C3—H3	121.5	C14A—C13—H13	121.4
C2—C3—H3	121.5	C12A—C13—H13	121.4
C3—C4—C5	122.64 (17)	F1A—C14A—C13	116.6 (2)
C3—C4—I1	117.87 (13)	F1A—C14A—C15	120.1 (2)
C5—C4—I1	119.49 (13)	C13—C14A—C15	123.3 (2)
C6—C5—C4	121.33 (17)	C14A—C15—C10	118.8 (2)
C6—C5—H5	119.3	C14A—C15—H15	120.6
C4—C5—H5	119.3	C10—C15—H15	120.6
C7—C6—C5	114.74 (16)	C17—C16—S1	110.13 (16)
C7—C6—C9	122.26 (17)	C17—C16—H16A	109.6
C5—C6—C9	122.97 (17)	S1—C16—H16A	109.6
O1—C7—C6	124.33 (16)	C17—C16—H16B	109.6
O1—C7—C2	110.45 (15)	S1—C16—H16B	109.6
C6—C7—C2	125.21 (17)	H16A—C16—H16B	108.1
C1—C8—O1	110.02 (16)	C16—C17—H17A	109.5
C1—C8—C10	135.75 (17)	C16—C17—H17B	109.5
O1—C8—C10	114.22 (15)	H17A—C17—H17B	109.5
C6—C9—H9A	109.5	C16—C17—H17C	109.5
C6—C9—H9B	109.5	H17A—C17—H17C	109.5
H9A—C9—H9B	109.5	H17B—C17—H17C	109.5
C6—C9—H9C	109.5
O2—S1—C1—C8	−135.41 (17)	C1—C2—C7—O1	−1.2 (2)
C16—S1—C1—C8	114.35 (18)	C3—C2—C7—C6	−1.2 (3)
O2—S1—C1—C2	38.91 (18)	C1—C2—C7—C6	179.34 (18)
C16—S1—C1—C2	−71.33 (18)	C2—C1—C8—O1	0.0 (2)
C8—C1—C2—C7	0.7 (2)	S1—C1—C8—O1	175.20 (13)
S1—C1—C2—C7	−174.51 (14)	C2—C1—C8—C10	179.08 (19)
C8—C1—C2—C3	−178.6 (2)	S1—C1—C8—C10	−5.8 (3)
S1—C1—C2—C3	6.2 (3)	C7—O1—C8—C1	−0.8 (2)
C7—C2—C3—C4	0.1 (3)	C7—O1—C8—C10	179.94 (14)
C1—C2—C3—C4	179.4 (2)	C1—C8—C10—C15	−15.3 (3)
C2—C3—C4—C5	1.5 (3)	O1—C8—C10—C15	163.69 (17)
C2—C3—C4—I1	−178.24 (13)	C1—C8—C10—C11	165.4 (2)
O2i—I1—C4—C3	−17.6 (4)	O1—C8—C10—C11	−15.5 (2)
O2i—I1—C4—C5	162.6 (2)	C15—C10—C11—C12A	−1.1 (3)
C3—C4—C5—C6	−2.2 (3)	C8—C10—C11—C12A	178.15 (18)
I1—C4—C5—C6	177.54 (14)	C10—C11—C12A—C13	1.2 (3)
C4—C5—C6—C7	1.1 (3)	C11—C12A—C13—C14A	−0.1 (3)
C4—C5—C6—C9	−177.08 (19)	C12A—C13—C14A—F1A	179.6 (2)
C8—O1—C7—C6	−179.30 (17)	C12A—C13—C14A—C15	−1.2 (4)
C8—O1—C7—C2	1.27 (19)	F1A—C14A—C15—C10	−179.6 (2)
C5—C6—C7—O1	−178.80 (16)	C13—C14A—C15—C10	1.3 (3)
C9—C6—C7—O1	−0.6 (3)	C11—C10—C15—C14A	−0.1 (3)
C5—C6—C7—C2	0.6 (3)	C8—C10—C15—C14A	−179.32 (19)
C9—C6—C7—C2	178.76 (18)	O2—S1—C16—C17	67.44 (18)
C3—C2—C7—O1	178.24 (16)	C1—S1—C16—C17	178.52 (17)