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

In the title compound, C(20)H(12)FIO(2)S, the dihedral angles between the mean plane [r.m.s. deviation = 0.014 (1) Å] of the benzofuran fragment and the pendant 4-fluoro-phenyl and phenyl rings are 8.0 (1) and 86.06 (6)°, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds. The crystal structure also exhibits weak π-π inter-actions between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.547 (2) Å, inter-planar distance = 3.397 (2) Å and slippage = 1.021 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C20H12FIO2S

M = 462.26

Triclinic,

a = 8.1771 (2) Å

b = 9.8877 (2) Å

c = 11.8423 (3) Å

α = 103.108 (1)°

β = 90.872 (1)°

γ = 111.546 (1)°

V = 862.23 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.00 mm−1

T = 173 K

0.27 × 0.26 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.516, T max = 0.746

15186 measured reflections

3974 independent reflections

3696 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.060

S = 1.07

3974 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.75 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/S1600536812013086/kj2197sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013086/kj2197Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013086/kj2197Isup3.cml

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

C20H12FIO2S	Z = 2
Mr = 462.26	F(000) = 452
Triclinic, P1	Dx = 1.780 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1771 (2) Å	Cell parameters from 9967 reflections
b = 9.8877 (2) Å	θ = 2.5–27.5°
c = 11.8423 (3) Å	µ = 2.00 mm−1
α = 103.108 (1)°	T = 173 K
β = 90.872 (1)°	Block, colourless
γ = 111.546 (1)°	0.27 × 0.26 × 0.12 mm
V = 862.23 (4) Å3

Bruker SMART APEXII CCD diffractometer	3974 independent reflections
Radiation source: rotating anode	3696 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.516, Tmax = 0.746	l = −15→15
15186 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)] = 0.024	Hydrogen site location: difference Fourier map
wR(F2) = 0.060	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0266P)2 + 0.5718P] where P = (Fo2 + 2Fc2)/3
3974 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.75 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	0.02004 (2)	0.736536 (19)	0.939462 (12)	0.04406 (7)
S1	0.04558 (6)	0.18031 (5)	0.55834 (4)	0.02240 (10)
F1	0.4764 (2)	0.12714 (16)	0.06431 (11)	0.0421 (3)
O1	0.29632 (18)	0.56238 (13)	0.46924 (11)	0.0224 (3)
O2	−0.10716 (18)	0.17443 (17)	0.62692 (14)	0.0317 (3)
C1	0.1437 (2)	0.36524 (19)	0.54025 (15)	0.0203 (3)
C2	0.1408 (2)	0.4983 (2)	0.61933 (15)	0.0212 (3)
C3	0.0716 (3)	0.5302 (2)	0.72497 (16)	0.0252 (4)
H3	0.0036	0.4528	0.7598	0.030*
C4	0.1067 (3)	0.6796 (2)	0.77636 (17)	0.0283 (4)
C5	0.2028 (3)	0.7961 (2)	0.72598 (18)	0.0296 (4)
H5	0.2227	0.8971	0.7644	0.035*
C6	0.2688 (3)	0.7648 (2)	0.62058 (17)	0.0267 (4)
H6	0.3329	0.8419	0.5843	0.032*
C7	0.2368 (2)	0.6155 (2)	0.57083 (15)	0.0217 (3)
C8	0.2380 (2)	0.40854 (19)	0.45144 (15)	0.0203 (3)
C9	0.2959 (2)	0.3331 (2)	0.34844 (15)	0.0212 (3)
C10	0.2368 (3)	0.1764 (2)	0.31272 (17)	0.0278 (4)
H10	0.1543	0.1169	0.3549	0.033*
C11	0.2971 (3)	0.1071 (2)	0.21679 (18)	0.0317 (4)
H11	0.2572	0.0007	0.1929	0.038*
C12	0.4154 (3)	0.1950 (2)	0.15691 (16)	0.0289 (4)
C13	0.4753 (3)	0.3489 (2)	0.18758 (17)	0.0283 (4)
H13	0.5565	0.4068	0.1439	0.034*
C14	0.4147 (3)	0.4179 (2)	0.28375 (16)	0.0248 (4)
H14	0.4545	0.5244	0.3059	0.030*
C15	0.2209 (2)	0.1910 (2)	0.65768 (16)	0.0226 (4)
C16	0.2111 (3)	0.2277 (3)	0.77601 (18)	0.0346 (5)
H16	0.1115	0.2458	0.8053	0.042*
C17	0.3483 (4)	0.2380 (3)	0.8519 (2)	0.0433 (6)
H17	0.3428	0.2630	0.9337	0.052*
C18	0.4935 (3)	0.2120 (3)	0.8089 (2)	0.0386 (5)
H18	0.5883	0.2211	0.8613	0.046*
C19	0.5009 (3)	0.1729 (2)	0.6898 (2)	0.0330 (4)
H19	0.6001	0.1541	0.6605	0.040*
C20	0.3635 (3)	0.1612 (2)	0.61308 (18)	0.0275 (4)
H20	0.3670	0.1331	0.5312	0.033*

	U11	U22	U33	U12	U13	U23
I1	0.04049 (10)	0.06314 (12)	0.02678 (8)	0.02727 (8)	0.00553 (6)	−0.00508 (7)
S1	0.0202 (2)	0.0189 (2)	0.0272 (2)	0.00549 (17)	0.00357 (17)	0.00708 (16)
F1	0.0526 (9)	0.0506 (8)	0.0284 (6)	0.0319 (7)	0.0107 (6)	−0.0008 (6)
O1	0.0269 (7)	0.0166 (6)	0.0225 (6)	0.0077 (5)	0.0037 (5)	0.0036 (5)
O2	0.0197 (7)	0.0361 (8)	0.0429 (8)	0.0101 (6)	0.0104 (6)	0.0171 (6)
C1	0.0192 (8)	0.0192 (8)	0.0230 (8)	0.0079 (7)	0.0014 (7)	0.0050 (6)
C2	0.0194 (9)	0.0219 (8)	0.0220 (8)	0.0090 (7)	−0.0003 (7)	0.0030 (7)
C3	0.0221 (9)	0.0305 (10)	0.0235 (9)	0.0116 (8)	0.0023 (7)	0.0046 (7)
C4	0.0250 (10)	0.0359 (10)	0.0230 (9)	0.0159 (9)	−0.0008 (7)	−0.0020 (7)
C5	0.0302 (11)	0.0250 (9)	0.0311 (10)	0.0141 (8)	−0.0030 (8)	−0.0033 (7)
C6	0.0281 (10)	0.0208 (9)	0.0300 (9)	0.0099 (8)	0.0000 (8)	0.0032 (7)
C7	0.0218 (9)	0.0223 (8)	0.0213 (8)	0.0101 (7)	0.0009 (7)	0.0029 (7)
C8	0.0201 (9)	0.0167 (8)	0.0232 (8)	0.0068 (7)	−0.0004 (7)	0.0038 (6)
C9	0.0216 (9)	0.0226 (8)	0.0194 (8)	0.0097 (7)	0.0006 (7)	0.0035 (7)
C10	0.0340 (11)	0.0228 (9)	0.0260 (9)	0.0106 (8)	0.0054 (8)	0.0049 (7)
C11	0.0414 (12)	0.0258 (9)	0.0281 (10)	0.0166 (9)	0.0011 (9)	0.0008 (8)
C12	0.0311 (11)	0.0391 (11)	0.0200 (8)	0.0217 (9)	0.0011 (8)	−0.0001 (8)
C13	0.0260 (10)	0.0367 (10)	0.0231 (9)	0.0131 (9)	0.0042 (7)	0.0069 (8)
C14	0.0245 (9)	0.0236 (9)	0.0247 (9)	0.0082 (8)	0.0019 (7)	0.0044 (7)
C15	0.0209 (9)	0.0199 (8)	0.0281 (9)	0.0074 (7)	0.0039 (7)	0.0089 (7)
C16	0.0363 (12)	0.0484 (13)	0.0304 (10)	0.0265 (11)	0.0095 (9)	0.0134 (9)
C17	0.0509 (15)	0.0615 (15)	0.0276 (10)	0.0328 (13)	0.0023 (10)	0.0115 (10)
C18	0.0343 (12)	0.0424 (12)	0.0439 (13)	0.0185 (10)	−0.0033 (10)	0.0139 (10)
C19	0.0247 (10)	0.0329 (11)	0.0477 (12)	0.0148 (9)	0.0083 (9)	0.0157 (9)
C20	0.0280 (10)	0.0255 (9)	0.0328 (10)	0.0125 (8)	0.0089 (8)	0.0103 (8)

I1—C4	2.096 (2)	C9—C10	1.399 (3)
S1—O2	1.4905 (15)	C10—C11	1.384 (3)
S1—C1	1.7716 (18)	C10—H10	0.9500
S1—C15	1.7978 (19)	C11—C12	1.371 (3)
F1—C12	1.353 (2)	C11—H11	0.9500
O1—C7	1.371 (2)	C12—C13	1.372 (3)
O1—C8	1.380 (2)	C13—C14	1.386 (3)
C1—C8	1.368 (3)	C13—H13	0.9500
C1—C2	1.440 (2)	C14—H14	0.9500
C2—C7	1.392 (3)	C15—C16	1.377 (3)
C2—C3	1.400 (3)	C15—C20	1.388 (3)
C3—C4	1.382 (3)	C16—C17	1.386 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.401 (3)	C17—C18	1.385 (4)
C5—C6	1.383 (3)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.384 (3)
C6—C7	1.383 (3)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.388 (3)
C8—C9	1.460 (2)	C19—H19	0.9500
C9—C14	1.397 (3)	C20—H20	0.9500
O2—S1—C1	107.18 (8)	C11—C10—H10	119.6
O2—S1—C15	106.52 (9)	C9—C10—H10	119.6
C1—S1—C15	97.14 (8)	C12—C11—C10	118.61 (19)
C7—O1—C8	106.99 (14)	C12—C11—H11	120.7
C8—C1—C2	107.66 (15)	C10—C11—H11	120.7
C8—C1—S1	126.91 (14)	F1—C12—C11	118.54 (19)
C2—C1—S1	125.42 (14)	F1—C12—C13	118.78 (19)
C7—C2—C3	119.34 (17)	C11—C12—C13	122.67 (18)
C7—C2—C1	104.82 (15)	C12—C13—C14	118.54 (19)
C3—C2—C1	135.82 (17)	C12—C13—H13	120.7
C4—C3—C2	116.96 (18)	C14—C13—H13	120.7
C4—C3—H3	121.5	C13—C14—C9	120.84 (18)
C2—C3—H3	121.5	C13—C14—H14	119.6
C3—C4—C5	122.95 (18)	C9—C14—H14	119.6
C3—C4—I1	118.98 (15)	C16—C15—C20	121.34 (18)
C5—C4—I1	118.05 (14)	C16—C15—S1	119.61 (15)
C6—C5—C4	120.26 (18)	C20—C15—S1	119.05 (15)
C6—C5—H5	119.9	C15—C16—C17	119.1 (2)
C4—C5—H5	119.9	C15—C16—H16	120.4
C7—C6—C5	116.56 (18)	C17—C16—H16	120.4
C7—C6—H6	121.7	C18—C17—C16	120.3 (2)
C5—C6—H6	121.7	C18—C17—H17	119.9
O1—C7—C6	125.34 (17)	C16—C17—H17	119.9
O1—C7—C2	110.74 (15)	C19—C18—C17	120.2 (2)
C6—C7—C2	123.92 (17)	C19—C18—H18	119.9
C1—C8—O1	109.79 (15)	C17—C18—H18	119.9
C1—C8—C9	135.62 (16)	C18—C19—C20	120.0 (2)
O1—C8—C9	114.52 (15)	C18—C19—H19	120.0
C14—C9—C10	118.46 (17)	C20—C19—H19	120.0
C14—C9—C8	119.83 (16)	C19—C20—C15	119.06 (19)
C10—C9—C8	121.71 (17)	C19—C20—H20	120.5
C11—C10—C9	120.86 (19)	C15—C20—H20	120.5
O2—S1—C1—C8	−153.19 (16)	C7—O1—C8—C9	−177.64 (15)
C15—S1—C1—C8	97.02 (18)	C1—C8—C9—C14	−170.7 (2)
O2—S1—C1—C2	28.24 (18)	O1—C8—C9—C14	5.9 (2)
C15—S1—C1—C2	−81.55 (17)	C1—C8—C9—C10	8.5 (3)
C8—C1—C2—C7	−0.1 (2)	O1—C8—C9—C10	−174.81 (17)
S1—C1—C2—C7	178.71 (13)	C14—C9—C10—C11	1.2 (3)
C8—C1—C2—C3	−178.5 (2)	C8—C9—C10—C11	−178.14 (18)
S1—C1—C2—C3	0.3 (3)	C9—C10—C11—C12	−0.3 (3)
C7—C2—C3—C4	−1.2 (3)	C10—C11—C12—F1	178.92 (18)
C1—C2—C3—C4	177.1 (2)	C10—C11—C12—C13	−0.6 (3)
C2—C3—C4—C5	1.6 (3)	F1—C12—C13—C14	−178.90 (18)
C2—C3—C4—I1	−176.41 (13)	C11—C12—C13—C14	0.6 (3)
C3—C4—C5—C6	−0.5 (3)	C12—C13—C14—C9	0.3 (3)
I1—C4—C5—C6	177.47 (15)	C10—C9—C14—C13	−1.1 (3)
C4—C5—C6—C7	−0.9 (3)	C8—C9—C14—C13	178.18 (17)
C8—O1—C7—C6	179.10 (18)	O2—S1—C15—C16	−15.33 (19)
C8—O1—C7—C2	0.1 (2)	C1—S1—C15—C16	95.01 (17)
C5—C6—C7—O1	−177.58 (18)	O2—S1—C15—C20	164.42 (15)
C5—C6—C7—C2	1.3 (3)	C1—S1—C15—C20	−85.24 (16)
C3—C2—C7—O1	178.77 (16)	C20—C15—C16—C17	1.3 (3)
C1—C2—C7—O1	0.0 (2)	S1—C15—C16—C17	−178.96 (18)
C3—C2—C7—C6	−0.3 (3)	C15—C16—C17—C18	0.2 (4)
C1—C2—C7—C6	−179.03 (18)	C16—C17—C18—C19	−1.2 (4)
C2—C1—C8—O1	0.1 (2)	C17—C18—C19—C20	0.7 (3)
S1—C1—C8—O1	−178.64 (13)	C18—C19—C20—C15	0.8 (3)
C2—C1—C8—C9	176.9 (2)	C16—C15—C20—C19	−1.8 (3)
S1—C1—C8—C9	−1.9 (3)	S1—C15—C20—C19	178.46 (15)
C7—O1—C8—C1	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2i	0.95	2.38	3.297 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2i	0.95	2.38	3.297 (3)	163

Symmetry code: (i) .