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

In the title compound, C16H12FIO2S, the dihedral angle between the plane of the benzo-furan ring system (r.m.s. deviation = 0.023 Å) and that of the 2-fluoro-phenyl ring is 39.78 (7)°. In the crystal, mol-ecules are linked via pairs of I⋯π contacts [3.812 (2) Å] and a π-π inter-action between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.821 (2) Å] into inversion dimers. These dimers are further linked by π-π inter-actions between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.668 (2) Å]. The mol-ecules stack along the a-axis direction. In addition, C-H⋯O hydrogen bonds are observed between inversion-related dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶, 2014 ▶).

Experimental

Crystal data

C16H12FIO2S

M = 414.22

Monoclinic,

a = 7.9460 (2) Å

b = 24.1545 (7) Å

c = 7.9685 (2) Å

β = 100.997 (1)°

V = 1501.32 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.28 mm−1

T = 173 K

0.42 × 0.40 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.541, T max = 0.746

14688 measured reflections

3721 independent reflections

3465 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.059

S = 1.12

3721 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.56 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814010459/hb7228sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010459/hb7228Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010459/hb7228Isup3.cml

CCDC reference: 1001669

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H12FIO2S	F(000) = 808
Mr = 414.22	Dx = 1.833 Mg m−3
Monoclinic, P21/c	Melting point = 470–469 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.9460 (2) Å	Cell parameters from 8240 reflections
b = 24.1545 (7) Å	θ = 2.6–28.3°
c = 7.9685 (2) Å	µ = 2.28 mm−1
β = 100.997 (1)°	T = 173 K
V = 1501.32 (7) Å3	Block, colourless
Z = 4	0.42 × 0.40 × 0.13 mm

Bruker SMART APEXII CCD diffractometer	3721 independent reflections
Radiation source: rotating anode	3465 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.025
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.7°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −32→27
Tmin = 0.541, Tmax = 0.746	l = −10→10
14688 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) = 0.059	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0242P)2 + 1.1461P] where P = (Fo2 + 2Fc2)/3
3721 reflections	(Δ/σ)max = 0.002
192 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.56 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	0.836495 (19)	0.586239 (6)	1.028521 (19)	0.02707 (6)
S1	0.69187 (7)	0.33626 (2)	0.73135 (7)	0.02286 (12)
F1	0.54937 (17)	0.31240 (6)	0.36409 (19)	0.0312 (3)
O1	0.31221 (18)	0.43857 (6)	0.56014 (19)	0.0199 (3)
O2	0.8687 (2)	0.35305 (8)	0.7161 (2)	0.0339 (4)
C1	0.5544 (3)	0.39339 (9)	0.6766 (3)	0.0202 (4)
C2	0.5700 (3)	0.44971 (9)	0.7398 (3)	0.0194 (4)
C3	0.6952 (3)	0.48077 (9)	0.8473 (3)	0.0221 (4)
H3	0.8019	0.4651	0.8998	0.026*
C4	0.6553 (3)	0.53565 (9)	0.8730 (3)	0.0214 (4)
C5	0.4976 (3)	0.55926 (9)	0.7989 (3)	0.0223 (4)
H5	0.4764	0.5970	0.8215	0.027*
C6	0.3717 (3)	0.52899 (9)	0.6932 (3)	0.0203 (4)
C7	0.4166 (3)	0.47492 (9)	0.6656 (3)	0.0192 (4)
C8	0.4009 (3)	0.38961 (9)	0.5680 (3)	0.0195 (4)
C9	0.1982 (3)	0.55220 (10)	0.6186 (3)	0.0284 (5)
H9A	0.1731	0.5456	0.4950	0.043*
H9B	0.1973	0.5921	0.6408	0.043*
H9C	0.1110	0.5340	0.6713	0.043*
C10	0.3059 (3)	0.34517 (9)	0.4659 (3)	0.0205 (4)
C11	0.3805 (3)	0.30761 (9)	0.3698 (3)	0.0240 (4)
C12	0.2887 (3)	0.26551 (10)	0.2777 (3)	0.0311 (5)
H12	0.3433	0.2403	0.2138	0.037*
C13	0.1158 (3)	0.26053 (11)	0.2799 (3)	0.0336 (6)
H13	0.0515	0.2310	0.2201	0.040*
C14	0.0361 (3)	0.29845 (11)	0.3690 (3)	0.0298 (5)
H14	−0.0836	0.2957	0.3669	0.036*
C15	0.1300 (3)	0.34039 (10)	0.4610 (3)	0.0234 (4)
H15	0.0741	0.3663	0.5215	0.028*
C16	0.6912 (4)	0.33410 (12)	0.9561 (3)	0.0344 (6)
H16A	0.7673	0.3044	1.0092	0.052*
H16B	0.5745	0.3270	0.9740	0.052*
H16C	0.7315	0.3696	1.0081	0.052*

	U11	U22	U33	U12	U13	U23
I1	0.02576 (9)	0.02477 (9)	0.02996 (9)	−0.00501 (5)	0.00348 (6)	−0.00525 (6)
S1	0.0252 (3)	0.0190 (3)	0.0238 (3)	0.0066 (2)	0.0033 (2)	−0.0005 (2)
F1	0.0262 (7)	0.0334 (8)	0.0364 (8)	0.0013 (6)	0.0118 (6)	−0.0074 (6)
O1	0.0192 (7)	0.0182 (8)	0.0213 (7)	0.0021 (6)	0.0018 (6)	−0.0012 (6)
O2	0.0231 (8)	0.0399 (10)	0.0395 (10)	0.0096 (7)	0.0082 (7)	0.0036 (8)
C1	0.0203 (10)	0.0188 (10)	0.0218 (10)	0.0031 (8)	0.0044 (8)	−0.0002 (8)
C2	0.0205 (10)	0.0174 (10)	0.0209 (10)	0.0010 (8)	0.0050 (8)	0.0005 (8)
C3	0.0200 (10)	0.0214 (11)	0.0242 (11)	0.0012 (8)	0.0028 (8)	−0.0002 (8)
C4	0.0227 (10)	0.0211 (11)	0.0209 (10)	−0.0032 (8)	0.0050 (8)	−0.0011 (8)
C5	0.0268 (11)	0.0162 (10)	0.0252 (11)	0.0006 (8)	0.0085 (9)	−0.0002 (8)
C6	0.0212 (10)	0.0192 (10)	0.0214 (10)	0.0036 (8)	0.0060 (8)	0.0025 (8)
C7	0.0189 (10)	0.0200 (11)	0.0192 (10)	0.0000 (8)	0.0049 (8)	−0.0010 (8)
C8	0.0209 (10)	0.0185 (10)	0.0193 (10)	0.0034 (8)	0.0050 (8)	0.0002 (8)
C9	0.0245 (11)	0.0232 (12)	0.0362 (13)	0.0075 (9)	0.0026 (10)	0.0011 (9)
C10	0.0236 (10)	0.0185 (11)	0.0183 (10)	0.0005 (8)	0.0011 (8)	0.0013 (8)
C11	0.0259 (11)	0.0233 (12)	0.0231 (11)	0.0014 (9)	0.0052 (9)	−0.0010 (8)
C12	0.0400 (14)	0.0257 (13)	0.0286 (12)	−0.0016 (10)	0.0089 (10)	−0.0084 (9)
C13	0.0404 (14)	0.0299 (13)	0.0289 (12)	−0.0116 (11)	0.0026 (10)	−0.0069 (10)
C14	0.0257 (11)	0.0348 (14)	0.0279 (12)	−0.0066 (10)	0.0024 (9)	0.0000 (10)
C15	0.0232 (10)	0.0235 (11)	0.0231 (11)	0.0006 (8)	0.0039 (8)	0.0006 (8)
C16	0.0433 (14)	0.0357 (14)	0.0246 (12)	0.0091 (11)	0.0077 (10)	0.0058 (10)

I1—C4	2.102 (2)	C8—C10	1.466 (3)
S1—O2	1.4898 (18)	C9—H9A	0.9800
S1—C1	1.763 (2)	C9—H9B	0.9800
S1—C16	1.793 (2)	C9—H9C	0.9800
F1—C11	1.356 (3)	C10—C11	1.391 (3)
O1—C8	1.372 (3)	C10—C15	1.396 (3)
O1—C7	1.378 (2)	C11—C12	1.379 (3)
C1—C8	1.357 (3)	C12—C13	1.383 (4)
C1—C2	1.448 (3)	C12—H12	0.9500
C2—C7	1.389 (3)	C13—C14	1.384 (4)
C2—C3	1.400 (3)	C13—H13	0.9500
C3—C4	1.387 (3)	C14—C15	1.383 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.401 (3)	C15—H15	0.9500
C5—C6	1.387 (3)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.383 (3)	C16—H16C	0.9800
C6—C9	1.502 (3)
O2—S1—C1	108.46 (10)	C6—C9—H9B	109.5
O2—S1—C16	105.79 (12)	H9A—C9—H9B	109.5
C1—S1—C16	98.65 (11)	C6—C9—H9C	109.5
C8—O1—C7	106.08 (16)	H9A—C9—H9C	109.5
C8—C1—C2	106.99 (18)	H9B—C9—H9C	109.5
C8—C1—S1	122.98 (17)	C11—C10—C15	117.4 (2)
C2—C1—S1	129.91 (16)	C11—C10—C8	123.7 (2)
C7—C2—C3	119.2 (2)	C15—C10—C8	118.9 (2)
C7—C2—C1	104.70 (18)	F1—C11—C12	118.1 (2)
C3—C2—C1	136.0 (2)	F1—C11—C10	119.4 (2)
C4—C3—C2	116.5 (2)	C12—C11—C10	122.4 (2)
C4—C3—H3	121.7	C11—C12—C13	118.9 (2)
C2—C3—H3	121.7	C11—C12—H12	120.5
C3—C4—C5	122.5 (2)	C13—C12—H12	120.5
C3—C4—I1	119.52 (16)	C12—C13—C14	120.1 (2)
C5—C4—I1	117.95 (16)	C12—C13—H13	119.9
C6—C5—C4	121.7 (2)	C14—C13—H13	119.9
C6—C5—H5	119.2	C15—C14—C13	120.2 (2)
C4—C5—H5	119.2	C15—C14—H14	119.9
C7—C6—C5	114.60 (19)	C13—C14—H14	119.9
C7—C6—C9	122.3 (2)	C14—C15—C10	120.8 (2)
C5—C6—C9	123.0 (2)	C14—C15—H15	119.6
O1—C7—C6	123.72 (19)	C10—C15—H15	119.6
O1—C7—C2	110.94 (18)	S1—C16—H16A	109.5
C6—C7—C2	125.3 (2)	S1—C16—H16B	109.5
C1—C8—O1	111.24 (18)	H16A—C16—H16B	109.5
C1—C8—C10	135.1 (2)	S1—C16—H16C	109.5
O1—C8—C10	113.59 (17)	H16A—C16—H16C	109.5
C6—C9—H9A	109.5	H16B—C16—H16C	109.5
O2—S1—C1—C8	132.80 (19)	C3—C2—C7—C6	−2.5 (3)
C16—S1—C1—C8	−117.3 (2)	C1—C2—C7—C6	178.2 (2)
O2—S1—C1—C2	−51.8 (2)	C2—C1—C8—O1	−2.2 (2)
C16—S1—C1—C2	58.1 (2)	S1—C1—C8—O1	174.07 (15)
C8—C1—C2—C7	2.1 (2)	C2—C1—C8—C10	−178.3 (2)
S1—C1—C2—C7	−173.83 (18)	S1—C1—C8—C10	−2.0 (4)
C8—C1—C2—C3	−177.0 (2)	C7—O1—C8—C1	1.4 (2)
S1—C1—C2—C3	7.0 (4)	C7—O1—C8—C10	178.36 (17)
C7—C2—C3—C4	0.4 (3)	C1—C8—C10—C11	−44.0 (4)
C1—C2—C3—C4	179.5 (2)	O1—C8—C10—C11	140.0 (2)
C2—C3—C4—C5	1.0 (3)	C1—C8—C10—C15	137.3 (3)
C2—C3—C4—I1	−178.86 (15)	O1—C8—C10—C15	−38.6 (3)
C3—C4—C5—C6	−0.6 (3)	C15—C10—C11—F1	176.76 (19)
I1—C4—C5—C6	179.31 (16)	C8—C10—C11—F1	−1.9 (3)
C4—C5—C6—C7	−1.3 (3)	C15—C10—C11—C12	−2.6 (3)
C4—C5—C6—C9	176.9 (2)	C8—C10—C11—C12	178.7 (2)
C8—O1—C7—C6	−179.5 (2)	F1—C11—C12—C13	−179.0 (2)
C8—O1—C7—C2	0.0 (2)	C10—C11—C12—C13	0.4 (4)
C5—C6—C7—O1	−177.70 (19)	C11—C12—C13—C14	2.0 (4)
C9—C6—C7—O1	4.1 (3)	C12—C13—C14—C15	−2.2 (4)
C5—C6—C7—C2	2.9 (3)	C13—C14—C15—C10	−0.1 (4)
C9—C6—C7—C2	−175.3 (2)	C11—C10—C15—C14	2.5 (3)
C3—C2—C7—O1	178.00 (18)	C8—C10—C15—C14	−178.8 (2)
C1—C2—C7—O1	−1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.95	2.49	3.355 (3)	151
C15—H15···O2ii	0.95	2.48	3.185 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.95	2.49	3.355 (3)	151
C15—H15⋯O2ii	0.95	2.48	3.185 (3)	131

Symmetry codes: (i) ; (ii) .