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

In the title compound, C(16)H(12)FIO(2)S, the 3-fluoro-phenyl ring makes a dihedral angle of 34.93 (7)° with the mean plane [r.m.s. deviation = 0.019 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked via pairs of I⋯O contacts [3.088 (2) Å] into inversion dimers. These dimers are connected by weak C-H⋯O hydrogen bonds.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2010 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H12FIO2S

M = 414.22

Monoclinic,

a = 7.8169 (1) Å

b = 23.9721 (3) Å

c = 8.0559 (1) Å

β = 99.748 (1)°

V = 1487.78 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.30 mm−1

T = 173 K

0.30 × 0.22 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.570, T max = 0.746

14066 measured reflections

3424 independent reflections

3226 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.052

S = 1.10

3424 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.55 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/S1600536812018697/bt5901sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018697/bt5901Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018697/bt5901Isup3.cml

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

C16H12FIO2S	F(000) = 808
Mr = 414.22	Dx = 1.849 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8987 reflections
a = 7.8169 (1) Å	θ = 2.7–27.5°
b = 23.9721 (3) Å	µ = 2.30 mm−1
c = 8.0559 (1) Å	T = 173 K
β = 99.748 (1)°	Block, colourless
V = 1487.78 (3) Å3	0.30 × 0.22 × 0.19 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3424 independent reflections
Radiation source: rotating anode	3226 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.025
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.7°
φ and ω scans	h = −10→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −31→30
Tmin = 0.570, Tmax = 0.746	l = −10→10
14066 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)] = 0.021	Hydrogen site location: difference Fourier map
wR(F2) = 0.052	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0225P)2 + 1.0726P] where P = (Fo2 + 2Fc2)/3
3424 reflections	(Δ/σ)max = 0.002
192 parameters	Δρmax = 0.45 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
I1	0.830625 (17)	0.412987 (6)	1.026115 (17)	0.02457 (6)
S1	0.70761 (6)	0.66239 (2)	0.72019 (6)	0.02102 (11)
F1	−0.11935 (17)	0.70760 (6)	0.33734 (19)	0.0382 (3)
O1	0.31305 (17)	0.56234 (6)	0.56108 (17)	0.0187 (3)
O2	0.88641 (19)	0.64247 (7)	0.7119 (2)	0.0298 (3)
C1	0.5622 (3)	0.60638 (8)	0.6682 (2)	0.0192 (4)
C2	0.5730 (2)	0.54990 (8)	0.7341 (2)	0.0185 (4)
C3	0.6967 (3)	0.51834 (8)	0.8398 (3)	0.0212 (4)
H3	0.8058	0.5336	0.8886	0.025*
C4	0.6524 (3)	0.46397 (8)	0.8699 (2)	0.0204 (4)
C5	0.4901 (3)	0.44112 (8)	0.8021 (2)	0.0207 (4)
H5	0.4652	0.4037	0.8283	0.025*
C6	0.3652 (2)	0.47188 (8)	0.6978 (2)	0.0193 (4)
C7	0.4151 (2)	0.52550 (8)	0.6654 (2)	0.0182 (4)
C8	0.4067 (2)	0.61080 (8)	0.5635 (2)	0.0177 (4)
C9	0.1873 (3)	0.44943 (9)	0.6296 (3)	0.0272 (5)
H9A	0.1000	0.4706	0.6774	0.041*
H9B	0.1813	0.4100	0.6603	0.041*
H9C	0.1648	0.4531	0.5067	0.041*
C10	0.3182 (2)	0.65543 (8)	0.4579 (2)	0.0184 (4)
C11	0.4081 (3)	0.69255 (9)	0.3707 (3)	0.0240 (4)
H11	0.5301	0.6890	0.3772	0.029*
C12	0.3186 (3)	0.73475 (10)	0.2744 (3)	0.0301 (5)
H12	0.3802	0.7600	0.2153	0.036*
C13	0.1406 (3)	0.74046 (10)	0.2636 (3)	0.0300 (5)
H13	0.0792	0.7698	0.2001	0.036*
C14	0.0562 (3)	0.70246 (9)	0.3474 (3)	0.0253 (4)
C15	0.1381 (3)	0.65996 (9)	0.4442 (2)	0.0203 (4)
H15	0.0743	0.6344	0.5002	0.024*
C16	0.6965 (3)	0.66712 (10)	0.9404 (3)	0.0308 (5)
H16A	0.7382	0.6322	0.9964	0.046*
H16B	0.5760	0.6736	0.9545	0.046*
H16C	0.7691	0.6981	0.9905	0.046*

	U11	U22	U33	U12	U13	U23
I1	0.02277 (8)	0.02225 (8)	0.02801 (8)	0.00522 (5)	0.00230 (6)	0.00455 (5)
S1	0.0205 (2)	0.0182 (2)	0.0234 (2)	−0.00496 (18)	0.00100 (19)	0.00187 (18)
F1	0.0224 (7)	0.0458 (9)	0.0453 (8)	0.0121 (6)	0.0022 (6)	0.0103 (7)
O1	0.0175 (6)	0.0161 (7)	0.0213 (6)	−0.0019 (5)	0.0002 (5)	0.0015 (5)
O2	0.0183 (7)	0.0381 (9)	0.0330 (8)	−0.0056 (6)	0.0044 (6)	−0.0003 (7)
C1	0.0189 (9)	0.0177 (9)	0.0211 (9)	−0.0020 (7)	0.0033 (7)	0.0010 (7)
C2	0.0185 (9)	0.0158 (9)	0.0215 (9)	−0.0006 (7)	0.0045 (7)	−0.0007 (7)
C3	0.0166 (9)	0.0213 (10)	0.0250 (10)	−0.0002 (7)	0.0018 (8)	−0.0002 (8)
C4	0.0210 (9)	0.0201 (10)	0.0201 (9)	0.0040 (7)	0.0033 (8)	0.0024 (7)
C5	0.0224 (10)	0.0163 (10)	0.0246 (10)	−0.0008 (7)	0.0071 (8)	0.0002 (7)
C6	0.0191 (9)	0.0180 (10)	0.0211 (9)	−0.0021 (7)	0.0040 (7)	−0.0020 (7)
C7	0.0169 (9)	0.0185 (10)	0.0191 (9)	0.0004 (7)	0.0032 (7)	0.0007 (7)
C8	0.0177 (9)	0.0168 (9)	0.0193 (9)	−0.0019 (7)	0.0050 (7)	0.0000 (7)
C9	0.0212 (10)	0.0232 (11)	0.0353 (11)	−0.0064 (8)	−0.0002 (9)	0.0009 (9)
C10	0.0203 (9)	0.0169 (9)	0.0173 (9)	−0.0003 (7)	0.0012 (7)	−0.0003 (7)
C11	0.0222 (10)	0.0252 (11)	0.0249 (10)	−0.0013 (8)	0.0050 (8)	0.0026 (8)
C12	0.0346 (12)	0.0257 (11)	0.0305 (11)	−0.0036 (9)	0.0070 (9)	0.0091 (9)
C13	0.0361 (12)	0.0248 (11)	0.0274 (10)	0.0060 (9)	0.0004 (9)	0.0068 (9)
C14	0.0213 (10)	0.0283 (11)	0.0251 (10)	0.0064 (8)	0.0010 (8)	−0.0002 (8)
C15	0.0210 (9)	0.0198 (10)	0.0200 (9)	−0.0009 (7)	0.0030 (7)	−0.0011 (7)
C16	0.0372 (12)	0.0309 (12)	0.0245 (10)	−0.0044 (10)	0.0063 (9)	−0.0049 (9)

I1—C4	2.1034 (19)	C6—C9	1.505 (3)
I1—O2i	3.0876 (16)	C8—C10	1.466 (3)
S1—O2	1.4891 (16)	C9—H9A	0.9800
S1—C1	1.763 (2)	C9—H9B	0.9800
S1—C16	1.795 (2)	C9—H9C	0.9800
F1—C14	1.366 (2)	C10—C11	1.395 (3)
O1—C8	1.371 (2)	C10—C15	1.398 (3)
O1—C7	1.376 (2)	C11—C12	1.390 (3)
C1—C8	1.361 (3)	C11—H11	0.9500
C1—C2	1.451 (3)	C12—C13	1.386 (3)
C2—C7	1.393 (3)	C12—H12	0.9500
C2—C3	1.397 (3)	C13—C14	1.368 (3)
C3—C4	1.380 (3)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.374 (3)
C4—C5	1.405 (3)	C15—H15	0.9500
C5—C6	1.388 (3)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.381 (3)	C16—H16C	0.9800
C4—I1—O2i	169.86 (6)	C6—C9—H9B	109.5
O2—S1—C1	108.51 (9)	H9A—C9—H9B	109.5
O2—S1—C16	105.52 (10)	C6—C9—H9C	109.5
C1—S1—C16	98.38 (10)	H9A—C9—H9C	109.5
C8—O1—C7	106.39 (14)	H9B—C9—H9C	109.5
C8—C1—C2	106.86 (17)	C11—C10—C15	119.85 (18)
C8—C1—S1	124.05 (15)	C11—C10—C8	121.95 (18)
C2—C1—S1	128.91 (14)	C15—C10—C8	118.20 (17)
C7—C2—C3	119.33 (18)	C12—C11—C10	119.7 (2)
C7—C2—C1	104.67 (16)	C12—C11—H11	120.1
C3—C2—C1	136.00 (18)	C10—C11—H11	120.1
C4—C3—C2	116.76 (18)	C13—C12—C11	120.8 (2)
C4—C3—H3	121.6	C13—C12—H12	119.6
C2—C3—H3	121.6	C11—C12—H12	119.6
C3—C4—C5	122.44 (18)	C14—C13—C12	117.8 (2)
C3—C4—I1	119.57 (14)	C14—C13—H13	121.1
C5—C4—I1	117.98 (15)	C12—C13—H13	121.1
C6—C5—C4	121.68 (19)	F1—C14—C13	118.30 (19)
C6—C5—H5	119.2	F1—C14—C15	117.87 (19)
C4—C5—H5	119.2	C13—C14—C15	123.8 (2)
C7—C6—C5	114.62 (18)	C14—C15—C10	117.96 (19)
C7—C6—C9	122.47 (18)	C14—C15—H15	121.0
C5—C6—C9	122.89 (19)	C10—C15—H15	121.0
O1—C7—C6	124.02 (17)	S1—C16—H16A	109.5
O1—C7—C2	110.87 (17)	S1—C16—H16B	109.5
C6—C7—C2	125.11 (18)	H16A—C16—H16B	109.5
C1—C8—O1	111.17 (17)	S1—C16—H16C	109.5
C1—C8—C10	134.49 (18)	H16A—C16—H16C	109.5
O1—C8—C10	114.33 (16)	H16B—C16—H16C	109.5
C6—C9—H9A	109.5
O2—S1—C1—C8	−136.08 (17)	C3—C2—C7—O1	−178.14 (17)
C16—S1—C1—C8	114.37 (19)	C1—C2—C7—O1	1.4 (2)
O2—S1—C1—C2	49.5 (2)	C3—C2—C7—C6	2.5 (3)
C16—S1—C1—C2	−60.0 (2)	C1—C2—C7—C6	−177.92 (19)
C8—C1—C2—C7	−2.2 (2)	C2—C1—C8—O1	2.2 (2)
S1—C1—C2—C7	172.98 (16)	S1—C1—C8—O1	−173.22 (14)
C8—C1—C2—C3	177.3 (2)	C2—C1—C8—C10	−179.2 (2)
S1—C1—C2—C3	−7.6 (4)	S1—C1—C8—C10	5.3 (3)
C7—C2—C3—C4	−0.2 (3)	C7—O1—C8—C1	−1.4 (2)
C1—C2—C3—C4	−179.6 (2)	C7—O1—C8—C10	179.76 (16)
C2—C3—C4—C5	−1.5 (3)	C1—C8—C10—C11	37.1 (3)
C2—C3—C4—I1	179.60 (14)	O1—C8—C10—C11	−144.37 (18)
O2i—I1—C4—C3	31.2 (5)	C1—C8—C10—C15	−143.5 (2)
O2i—I1—C4—C5	−147.7 (3)	O1—C8—C10—C15	35.0 (2)
C3—C4—C5—C6	1.1 (3)	C15—C10—C11—C12	1.7 (3)
I1—C4—C5—C6	−179.97 (15)	C8—C10—C11—C12	−178.94 (19)
C4—C5—C6—C7	1.0 (3)	C10—C11—C12—C13	−0.1 (3)
C4—C5—C6—C9	−177.2 (2)	C11—C12—C13—C14	−1.5 (3)
C8—O1—C7—C6	179.23 (18)	C12—C13—C14—F1	−179.9 (2)
C8—O1—C7—C2	−0.1 (2)	C12—C13—C14—C15	1.5 (3)
C5—C6—C7—O1	177.90 (18)	F1—C14—C15—C10	−178.52 (18)
C9—C6—C7—O1	−3.9 (3)	C13—C14—C15—C10	0.1 (3)
C5—C6—C7—C2	−2.8 (3)	C11—C10—C15—C14	−1.7 (3)
C9—C6—C7—C2	175.3 (2)	C8—C10—C15—C14	178.90 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2ii	0.95	2.44	3.183 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2i	0.95	2.44	3.183 (3)	135

Symmetry code: (i) .