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

In the title compound, C(16)H(12)FIO(2)S, the 4-fluoro-phenyl ring is rotated slightly out of the benzofuran plane, as indicated by the dihedral angle of 4.48 (5)°. In the crystal structure, pairs of I⋯O halogen bonds [I⋯O = 3.123 (1) Å] link the mol-ecules into centrosymmetric dimers. These dimers are further linked via aromatic π-π inter-actions between the benzene and 4-fluoro-phenyl rings of neighbouring mol-ecules [centroid-centroid distance = 3.620 (3) Å].

Related literature

For the crystal structures of similar 3-ethyl­sulfinyl-2-(4-fluoro­phen­yl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010 ▶). 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 a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H12FIO2S

M = 414.22

Triclinic,

a = 7.2942 (4) Å

b = 9.6312 (5) Å

c = 11.0132 (6) Å

α = 100.637 (2)°

β = 97.947 (2)°

γ = 105.086 (2)°

V = 719.91 (7) Å3

Z = 2

Mo Kα radiation

μ = 2.38 mm−1

T = 173 K

0.38 × 0.18 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.548, T max = 0.746

12738 measured reflections

3342 independent reflections

3237 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.052

S = 1.11

3342 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.63 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/S1600536810012717/ds2026sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012717/ds2026Isup2.hkl

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

C16H12FIO2S	Z = 2
Mr = 414.22	F(000) = 404
Triclinic, P1	Dx = 1.911 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2942 (4) Å	Cell parameters from 9908 reflections
b = 9.6312 (5) Å	θ = 2.6–27.6°
c = 11.0132 (6) Å	µ = 2.38 mm−1
α = 100.637 (2)°	T = 173 K
β = 97.947 (2)°	Block, colourless
γ = 105.086 (2)°	0.38 × 0.18 × 0.11 mm
V = 719.91 (7) Å3

Bruker SMART APEXII CCD diffractometer	3342 independent reflections
Radiation source: Rotating Anode	3237 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.9°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.548, Tmax = 0.746	l = −14→14
12738 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)] = 0.019	Hydrogen site location: difference Fourier map
wR(F2) = 0.052	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0269P)2 + 0.2687P] where P = (Fo2 + 2Fc2)/3
3342 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.63 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	0.226555 (16)	0.736460 (12)	1.062556 (10)	0.02602 (5)
S	0.04077 (6)	0.19740 (5)	0.59260 (4)	0.02146 (9)
F	0.23547 (19)	0.15061 (15)	−0.01197 (11)	0.0389 (3)
O1	0.29054 (17)	0.57530 (13)	0.50405 (11)	0.0205 (2)
O2	−0.0999 (2)	0.20821 (16)	0.67760 (14)	0.0322 (3)
C1	0.1561 (2)	0.37895 (18)	0.57995 (16)	0.0197 (3)
C2	0.2016 (2)	0.51016 (18)	0.68023 (16)	0.0190 (3)
C3	0.1835 (2)	0.53995 (19)	0.80655 (16)	0.0207 (3)
H3	0.1287	0.4630	0.8455	0.025*
C4	0.2487 (2)	0.68639 (19)	0.87246 (16)	0.0213 (3)
C5	0.3272 (3)	0.8028 (2)	0.81686 (18)	0.0246 (4)
H5	0.3683	0.9018	0.8652	0.030*
C6	0.3448 (3)	0.77340 (19)	0.69133 (17)	0.0231 (3)
H6	0.3972	0.8502	0.6517	0.028*
C7	0.2821 (2)	0.62657 (18)	0.62715 (16)	0.0193 (3)
C8	0.2123 (2)	0.42343 (18)	0.47623 (16)	0.0189 (3)
C9	0.2136 (2)	0.35025 (19)	0.34774 (16)	0.0199 (3)
C10	0.1546 (3)	0.1962 (2)	0.30668 (18)	0.0255 (4)
H10	0.1113	0.1371	0.3632	0.031*
C11	0.1583 (3)	0.1286 (2)	0.18520 (19)	0.0290 (4)
H11	0.1152	0.0240	0.1571	0.035*
C12	0.2255 (3)	0.2160 (2)	0.10629 (17)	0.0269 (4)
C13	0.2847 (3)	0.3683 (2)	0.14173 (18)	0.0282 (4)
H13	0.3299	0.4258	0.0846	0.034*
C14	0.2767 (3)	0.4354 (2)	0.26295 (17)	0.0252 (3)
H14	0.3144	0.5402	0.2887	0.030*
C15	0.2486 (3)	0.1670 (2)	0.68306 (18)	0.0267 (4)
H15A	0.3105	0.2532	0.7547	0.032*
H15B	0.2047	0.0789	0.7178	0.032*
C16	0.3954 (3)	0.1442 (2)	0.6025 (2)	0.0296 (4)
H16A	0.3359	0.0565	0.5335	0.044*
H16B	0.5069	0.1304	0.6543	0.044*
H16C	0.4384	0.2310	0.5676	0.044*

	U11	U22	U33	U12	U13	U23
I	0.03240 (8)	0.02619 (8)	0.01896 (8)	0.01017 (5)	0.00499 (5)	0.00175 (5)
S	0.02080 (19)	0.01889 (19)	0.0227 (2)	0.00112 (15)	0.00640 (15)	0.00498 (15)
F	0.0464 (7)	0.0480 (7)	0.0218 (6)	0.0179 (6)	0.0109 (5)	−0.0020 (5)
O1	0.0239 (6)	0.0181 (6)	0.0198 (6)	0.0050 (5)	0.0068 (4)	0.0052 (4)
O2	0.0285 (7)	0.0332 (7)	0.0361 (8)	0.0043 (6)	0.0180 (6)	0.0092 (6)
C1	0.0184 (7)	0.0185 (8)	0.0214 (8)	0.0039 (6)	0.0045 (6)	0.0039 (6)
C2	0.0166 (7)	0.0191 (7)	0.0213 (8)	0.0052 (6)	0.0045 (6)	0.0043 (6)
C3	0.0193 (7)	0.0226 (8)	0.0208 (8)	0.0057 (6)	0.0060 (6)	0.0051 (6)
C4	0.0202 (7)	0.0247 (8)	0.0197 (8)	0.0090 (6)	0.0045 (6)	0.0027 (6)
C5	0.0254 (8)	0.0193 (8)	0.0279 (9)	0.0069 (7)	0.0041 (7)	0.0027 (7)
C6	0.0254 (8)	0.0186 (8)	0.0261 (9)	0.0062 (6)	0.0068 (7)	0.0065 (6)
C7	0.0189 (7)	0.0205 (8)	0.0200 (8)	0.0072 (6)	0.0052 (6)	0.0050 (6)
C8	0.0172 (7)	0.0168 (7)	0.0222 (8)	0.0046 (6)	0.0039 (6)	0.0040 (6)
C9	0.0171 (7)	0.0246 (8)	0.0190 (8)	0.0076 (6)	0.0039 (6)	0.0048 (6)
C10	0.0271 (9)	0.0231 (8)	0.0258 (9)	0.0056 (7)	0.0084 (7)	0.0046 (7)
C11	0.0297 (9)	0.0254 (9)	0.0284 (9)	0.0077 (7)	0.0053 (7)	−0.0013 (7)
C12	0.0251 (8)	0.0363 (10)	0.0189 (8)	0.0131 (8)	0.0040 (6)	0.0000 (7)
C13	0.0304 (9)	0.0360 (10)	0.0222 (9)	0.0126 (8)	0.0079 (7)	0.0102 (8)
C14	0.0277 (9)	0.0251 (9)	0.0236 (9)	0.0082 (7)	0.0055 (7)	0.0061 (7)
C15	0.0295 (9)	0.0243 (9)	0.0266 (9)	0.0068 (7)	0.0040 (7)	0.0096 (7)
C16	0.0249 (8)	0.0261 (9)	0.0375 (11)	0.0073 (7)	0.0039 (8)	0.0085 (8)

I—C4	2.098 (2)	C6—H6	0.9500
I—O2i	3.123 (1)	C8—C9	1.462 (2)
S—O2	1.492 (1)	C9—C10	1.399 (2)
S—C1	1.772 (2)	C9—C14	1.401 (2)
S—C15	1.816 (2)	C10—C11	1.383 (3)
F—C12	1.358 (2)	C10—H10	0.9500
O1—C7	1.370 (2)	C11—C12	1.370 (3)
O1—C8	1.382 (2)	C11—H11	0.9500
C1—C8	1.369 (2)	C12—C13	1.379 (3)
C1—C2	1.446 (2)	C13—C14	1.388 (3)
C2—C7	1.392 (2)	C13—H13	0.9500
C2—C3	1.399 (2)	C14—H14	0.9500
C3—C4	1.386 (2)	C15—C16	1.515 (3)
C3—H3	0.9500	C15—H15A	0.9900
C4—C5	1.406 (3)	C15—H15B	0.9900
C5—C6	1.390 (3)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.383 (2)	C16—H16C	0.9800
C4—I—O2i	167.88 (5)	C10—C9—C8	121.74 (16)
O2—S—C1	107.52 (8)	C14—C9—C8	119.67 (15)
O2—S—C15	107.08 (9)	C11—C10—C9	121.07 (17)
C1—S—C15	97.46 (8)	C11—C10—H10	119.5
C7—O1—C8	107.01 (13)	C9—C10—H10	119.5
C8—C1—C2	107.24 (14)	C12—C11—C10	118.44 (17)
C8—C1—S	127.97 (13)	C12—C11—H11	120.8
C2—C1—S	124.75 (13)	C10—C11—H11	120.8
C7—C2—C3	119.36 (16)	F—C12—C11	118.94 (17)
C7—C2—C1	105.00 (15)	F—C12—C13	118.20 (18)
C3—C2—C1	135.64 (16)	C11—C12—C13	122.86 (17)
C4—C3—C2	117.18 (16)	C12—C13—C14	118.37 (18)
C4—C3—H3	121.4	C12—C13—H13	120.8
C2—C3—H3	121.4	C14—C13—H13	120.8
C3—C4—C5	122.70 (16)	C13—C14—C9	120.64 (17)
C3—C4—I	118.59 (13)	C13—C14—H14	119.7
C5—C4—I	118.71 (13)	C9—C14—H14	119.7
C6—C5—C4	120.18 (16)	C16—C15—S	111.38 (13)
C6—C5—H5	119.9	C16—C15—H15A	109.4
C4—C5—H5	119.9	S—C15—H15A	109.4
C7—C6—C5	116.55 (16)	C16—C15—H15B	109.4
C7—C6—H6	121.7	S—C15—H15B	109.4
C5—C6—H6	121.7	H15A—C15—H15B	108.0
O1—C7—C6	125.25 (15)	C15—C16—H16A	109.5
O1—C7—C2	110.72 (14)	C15—C16—H16B	109.5
C6—C7—C2	124.02 (16)	H16A—C16—H16B	109.5
C1—C8—O1	110.02 (14)	C15—C16—H16C	109.5
C1—C8—C9	135.88 (16)	H16A—C16—H16C	109.5
O1—C8—C9	114.08 (14)	H16B—C16—H16C	109.5
C10—C9—C14	118.59 (16)
O2—S—C1—C8	−143.28 (16)	C2—C1—C8—O1	−0.15 (18)
C15—S—C1—C8	106.12 (17)	S—C1—C8—O1	177.70 (12)
O2—S—C1—C2	34.22 (16)	C2—C1—C8—C9	177.97 (17)
C15—S—C1—C2	−76.38 (15)	S—C1—C8—C9	−4.2 (3)
C8—C1—C2—C7	0.56 (18)	C7—O1—C8—C1	−0.33 (18)
S—C1—C2—C7	−177.37 (12)	C7—O1—C8—C9	−178.90 (13)
C8—C1—C2—C3	−179.12 (18)	C1—C8—C9—C10	−3.3 (3)
S—C1—C2—C3	2.9 (3)	O1—C8—C9—C10	174.74 (15)
C7—C2—C3—C4	−0.2 (2)	C1—C8—C9—C14	177.15 (19)
C1—C2—C3—C4	179.41 (18)	O1—C8—C9—C14	−4.8 (2)
C2—C3—C4—C5	1.1 (2)	C14—C9—C10—C11	0.1 (3)
C2—C3—C4—I	−179.54 (12)	C8—C9—C10—C11	−179.44 (16)
C3—C4—C5—C6	−1.0 (3)	C9—C10—C11—C12	1.5 (3)
I—C4—C5—C6	179.69 (13)	C10—C11—C12—F	177.94 (16)
C4—C5—C6—C7	−0.1 (3)	C10—C11—C12—C13	−1.8 (3)
C8—O1—C7—C6	−179.49 (16)	F—C12—C13—C14	−179.32 (16)
C8—O1—C7—C2	0.71 (17)	C11—C12—C13—C14	0.4 (3)
C5—C6—C7—O1	−178.78 (15)	C12—C13—C14—C9	1.3 (3)
C5—C6—C7—C2	1.0 (3)	C10—C9—C14—C13	−1.5 (3)
C3—C2—C7—O1	178.96 (14)	C8—C9—C14—C13	178.04 (16)
C1—C2—C7—O1	−0.79 (18)	O2—S—C15—C16	176.25 (13)
C3—C2—C7—C6	−0.8 (2)	C1—S—C15—C16	−72.79 (14)
C1—C2—C7—C6	179.41 (16)