3-(3-Fluoro-phenyl-sulfin-yl)-5-iodo-2,7-dimethyl-1-benzofuran.

In the title compound, C(16)H(12)FIO(2)S, the 3-fluoro-phenyl ring makes a dihedral angle of 76.47 (6)° with the mean plane [r.m.s. deviation = 0.013 (2) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds,forming chains along the b-axis direction, and an I⋯O contact [3.204 (2) Å]. The crystal structure also exhibits slipped π-π inter-actions between the 3-fluoro-phenyl rings of neighbouring mol-ecules [centroid-centroid distance = 3.683 (3) Å and slippage = 1.708 (3) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2011 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H12FIO2S

M = 414.22

Monoclinic,

a = 8.3285 (3) Å

b = 15.1807 (5) Å

c = 12.2471 (4) Å

β = 90.250 (2)°

V = 1548.42 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.21 mm−1

T = 173 K

0.43 × 0.18 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.452, T max = 0.740

14445 measured reflections

3815 independent reflections

3409 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.065

S = 1.05

3815 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.71 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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037944/im2399sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037944/im2399Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037944/im2399Isup3.cml

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

C16H12FIO2S	F(000) = 808
Mr = 414.22	Dx = 1.777 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7687 reflections
a = 8.3285 (3) Å	θ = 2.7–28.3°
b = 15.1807 (5) Å	µ = 2.21 mm−1
c = 12.2471 (4) Å	T = 173 K
β = 90.250 (2)°	Block, colourless
V = 1548.42 (9) Å3	0.43 × 0.18 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3815 independent reflections
Radiation source: rotating anode	3409 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.1°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −20→20
Tmin = 0.452, Tmax = 0.740	l = −12→16
14445 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) = 0.065	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0282P)2 + 0.8484P] where P = (Fo2 + 2Fc2)/3
3815 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.71 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	0.567756 (18)	0.313250 (10)	0.587900 (13)	0.03495 (7)
S1	0.86223 (6)	0.46644 (4)	0.13656 (4)	0.02703 (12)
F1	0.26520 (17)	0.54480 (10)	0.13600 (12)	0.0441 (4)
C1	0.8607 (3)	0.52209 (14)	0.26168 (17)	0.0250 (4)
O1	0.90716 (19)	0.63275 (10)	0.37911 (13)	0.0289 (3)
O2	0.94638 (19)	0.38071 (11)	0.14941 (15)	0.0387 (4)
C2	0.8029 (2)	0.49449 (14)	0.36768 (16)	0.0238 (4)
C3	0.7257 (3)	0.42026 (14)	0.40952 (18)	0.0280 (4)
H3	0.7021	0.3706	0.3650	0.034*
C4	0.6852 (3)	0.42242 (15)	0.51872 (19)	0.0297 (5)
C5	0.7189 (3)	0.49477 (16)	0.58547 (18)	0.0325 (5)
H5	0.6886	0.4930	0.6601	0.039*
C6	0.7957 (3)	0.56934 (15)	0.54554 (18)	0.0298 (5)
C7	0.8348 (3)	0.56539 (14)	0.43646 (17)	0.0260 (4)
C8	0.9211 (3)	0.60468 (14)	0.27344 (18)	0.0273 (4)
C9	0.8290 (4)	0.64909 (17)	0.6148 (2)	0.0420 (6)
H9A	0.9398	0.6685	0.6033	0.063*
H9B	0.8138	0.6342	0.6919	0.063*
H9C	0.7550	0.6966	0.5943	0.063*
C10	0.9931 (3)	0.66853 (15)	0.1966 (2)	0.0378 (6)
H10A	0.9995	0.6420	0.1238	0.057*
H10B	1.1012	0.6842	0.2218	0.057*
H10C	0.9264	0.7216	0.1933	0.057*
C11	0.6519 (2)	0.44006 (14)	0.12914 (16)	0.0235 (4)
C12	0.5369 (3)	0.50573 (15)	0.14214 (16)	0.0272 (4)
H12	0.5655	0.5641	0.1624	0.033*
C13	0.3799 (3)	0.48178 (16)	0.12415 (17)	0.0297 (5)
C14	0.3321 (3)	0.39863 (17)	0.0960 (2)	0.0346 (5)
H14	0.2218	0.3849	0.0854	0.042*
C15	0.4494 (3)	0.33527 (16)	0.0835 (2)	0.0366 (5)
H15	0.4197	0.2770	0.0638	0.044*
C16	0.6107 (3)	0.35558 (16)	0.09950 (19)	0.0314 (5)
H16	0.6910	0.3118	0.0901	0.038*

	U11	U22	U33	U12	U13	U23
I1	0.03228 (10)	0.03571 (10)	0.03690 (10)	0.00319 (6)	0.00514 (7)	0.01028 (6)
S1	0.0235 (3)	0.0315 (3)	0.0261 (3)	−0.0005 (2)	0.0032 (2)	−0.0058 (2)
F1	0.0332 (7)	0.0563 (9)	0.0430 (8)	0.0206 (7)	0.0027 (6)	−0.0041 (7)
C1	0.0253 (10)	0.0242 (10)	0.0254 (10)	0.0023 (8)	0.0001 (8)	−0.0024 (8)
O1	0.0346 (8)	0.0227 (7)	0.0293 (8)	0.0007 (6)	−0.0009 (7)	−0.0027 (6)
O2	0.0259 (8)	0.0370 (9)	0.0530 (11)	0.0077 (7)	−0.0050 (8)	−0.0157 (8)
C2	0.0239 (10)	0.0252 (10)	0.0224 (10)	0.0032 (8)	−0.0017 (8)	−0.0013 (8)
C3	0.0303 (11)	0.0250 (10)	0.0287 (11)	0.0007 (9)	0.0003 (9)	−0.0012 (8)
C4	0.0284 (11)	0.0300 (11)	0.0306 (11)	0.0036 (9)	0.0012 (9)	0.0065 (9)
C5	0.0383 (13)	0.0366 (12)	0.0227 (10)	0.0081 (10)	0.0016 (9)	0.0006 (9)
C6	0.0343 (12)	0.0301 (11)	0.0251 (10)	0.0081 (9)	−0.0045 (9)	−0.0034 (9)
C7	0.0280 (11)	0.0225 (10)	0.0275 (11)	0.0046 (8)	−0.0031 (9)	−0.0010 (8)
C8	0.0281 (10)	0.0252 (10)	0.0285 (11)	0.0029 (8)	−0.0001 (9)	−0.0018 (8)
C9	0.0573 (17)	0.0371 (13)	0.0316 (13)	0.0050 (12)	−0.0034 (12)	−0.0101 (11)
C10	0.0481 (15)	0.0257 (11)	0.0398 (14)	−0.0026 (10)	0.0077 (12)	0.0023 (10)
C11	0.0226 (10)	0.0282 (10)	0.0198 (9)	0.0014 (8)	0.0017 (8)	0.0016 (8)
C12	0.0313 (11)	0.0301 (11)	0.0202 (10)	0.0059 (9)	0.0028 (8)	−0.0014 (8)
C13	0.0260 (11)	0.0419 (13)	0.0214 (10)	0.0121 (9)	0.0035 (8)	0.0034 (9)
C14	0.0238 (11)	0.0448 (14)	0.0353 (12)	−0.0015 (10)	0.0010 (9)	0.0094 (10)
C15	0.0317 (12)	0.0314 (12)	0.0466 (14)	−0.0049 (10)	−0.0017 (11)	0.0078 (10)
C16	0.0264 (11)	0.0295 (12)	0.0383 (13)	0.0033 (9)	−0.0001 (9)	0.0042 (9)

I1—C4	2.105 (2)	C6—C9	1.503 (3)
I1—O2i	3.2041 (16)	C8—C10	1.480 (3)
S1—O2	1.4862 (17)	C9—H9A	0.9800
S1—C1	1.750 (2)	C9—H9B	0.9800
S1—C11	1.798 (2)	C9—H9C	0.9800
F1—C13	1.360 (2)	C10—H10A	0.9800
C1—C8	1.358 (3)	C10—H10B	0.9800
C1—C2	1.449 (3)	C10—H10C	0.9800
O1—C8	1.368 (3)	C11—C16	1.376 (3)
O1—C7	1.381 (3)	C11—C12	1.392 (3)
C2—C7	1.392 (3)	C12—C13	1.374 (3)
C2—C3	1.396 (3)	C12—H12	0.9500
C3—C4	1.381 (3)	C13—C14	1.367 (3)
C3—H3	0.9500	C14—C15	1.380 (4)
C4—C5	1.397 (3)	C14—H14	0.9500
C5—C6	1.390 (3)	C15—C16	1.391 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.378 (3)	C16—H16	0.9500
C4—I1—O2i	165.03 (7)	C6—C9—H9B	109.5
O2—S1—C1	109.58 (10)	H9A—C9—H9B	109.5
O2—S1—C11	105.61 (10)	C6—C9—H9C	109.5
C1—S1—C11	98.11 (10)	H9A—C9—H9C	109.5
C8—C1—C2	107.24 (18)	H9B—C9—H9C	109.5
C8—C1—S1	122.30 (17)	C8—C10—H10A	109.5
C2—C1—S1	130.45 (16)	C8—C10—H10B	109.5
C8—O1—C7	106.85 (16)	H10A—C10—H10B	109.5
C7—C2—C3	119.29 (19)	C8—C10—H10C	109.5
C7—C2—C1	104.80 (18)	H10A—C10—H10C	109.5
C3—C2—C1	135.89 (19)	H10B—C10—H10C	109.5
C4—C3—C2	116.8 (2)	C16—C11—C12	121.8 (2)
C4—C3—H3	121.6	C16—C11—S1	117.57 (16)
C2—C3—H3	121.6	C12—C11—S1	120.35 (17)
C3—C4—C5	122.4 (2)	C13—C12—C11	116.6 (2)
C3—C4—I1	119.15 (17)	C13—C12—H12	121.7
C5—C4—I1	118.43 (17)	C11—C12—H12	121.7
C6—C5—C4	121.7 (2)	F1—C13—C14	118.2 (2)
C6—C5—H5	119.1	F1—C13—C12	117.7 (2)
C4—C5—H5	119.1	C14—C13—C12	124.1 (2)
C7—C6—C5	114.6 (2)	C13—C14—C15	117.8 (2)
C7—C6—C9	122.6 (2)	C13—C14—H14	121.1
C5—C6—C9	122.8 (2)	C15—C14—H14	121.1
C6—C7—O1	124.52 (19)	C14—C15—C16	120.9 (2)
C6—C7—C2	125.1 (2)	C14—C15—H15	119.5
O1—C7—C2	110.33 (18)	C16—C15—H15	119.5
C1—C8—O1	110.78 (19)	C11—C16—C15	118.9 (2)
C1—C8—C10	133.5 (2)	C11—C16—H16	120.5
O1—C8—C10	115.72 (19)	C15—C16—H16	120.5
C6—C9—H9A	109.5
O2—S1—C1—C8	123.85 (19)	C3—C2—C7—C6	−0.2 (3)
C11—S1—C1—C8	−126.32 (19)	C1—C2—C7—C6	178.1 (2)
O2—S1—C1—C2	−55.4 (2)	C3—C2—C7—O1	−178.33 (18)
C11—S1—C1—C2	54.4 (2)	C1—C2—C7—O1	0.0 (2)
C8—C1—C2—C7	0.0 (2)	C2—C1—C8—O1	0.1 (2)
S1—C1—C2—C7	179.29 (17)	S1—C1—C8—O1	−179.29 (15)
C8—C1—C2—C3	177.8 (2)	C2—C1—C8—C10	−178.4 (2)
S1—C1—C2—C3	−2.8 (4)	S1—C1—C8—C10	2.2 (4)
C7—C2—C3—C4	0.1 (3)	C7—O1—C8—C1	−0.1 (2)
C1—C2—C3—C4	−177.6 (2)	C7—O1—C8—C10	178.6 (2)
C2—C3—C4—C5	0.0 (3)	O2—S1—C11—C16	−21.3 (2)
C2—C3—C4—I1	179.77 (15)	C1—S1—C11—C16	−134.30 (18)
O2i—I1—C4—C3	34.5 (4)	O2—S1—C11—C12	165.15 (17)
O2i—I1—C4—C5	−145.8 (2)	C1—S1—C11—C12	52.11 (19)
C3—C4—C5—C6	0.0 (4)	C16—C11—C12—C13	0.2 (3)
I1—C4—C5—C6	−179.77 (17)	S1—C11—C12—C13	173.49 (15)
C4—C5—C6—C7	−0.1 (3)	C11—C12—C13—F1	−179.81 (18)
C4—C5—C6—C9	178.2 (2)	C11—C12—C13—C14	0.7 (3)
C5—C6—C7—O1	178.1 (2)	F1—C13—C14—C15	179.6 (2)
C9—C6—C7—O1	−0.2 (3)	C12—C13—C14—C15	−0.9 (4)
C5—C6—C7—C2	0.1 (3)	C13—C14—C15—C16	0.2 (4)
C9—C6—C7—C2	−178.1 (2)	C12—C11—C16—C15	−0.8 (3)
C8—O1—C7—C6	−178.1 (2)	S1—C11—C16—C15	−174.31 (19)
C8—O1—C7—C2	0.1 (2)	C14—C15—C16—C11	0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ii	0.95	2.43	3.292 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.95	2.43	3.292 (3)	151

Symmetry code: (i) .