3-(4-Fluoro-phenyl-sulfin-yl)-5-iodo-2-methyl-1-benzofuran.

In the title compound, C(15)H(10)FIO(2)S, the O atom and the 4-fluoro-phenyl group of the 4-fluoro-phenyl-sulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment; the 4-fluoro-phenyl ring is nearly perpendicular to this plane, making a dihedral angle of 83.37 (7)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds and an I⋯O inter-action [I⋯O = 3.255 (2) Å]. The crystal structure also exhibits inter-molecular C-F⋯π inter-actions [3.068 (2) Å], and aromatic π-π inter-actions between the furan and benzene rings of neighbouring benzofuran fragments [centroid-centroid distance = 3.636 (2) Å].

Related literature

For the crystal structures of similar 3-(4-fluoro­phenyl­sulfin­yl)-2-methyl-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

C15H10FIO2S

M = 400.19

Monoclinic,

a = 13.1665 (4) Å

b = 11.4338 (4) Å

c = 9.9296 (3) Å

β = 107.181 (1)°

V = 1428.13 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.40 mm−1

T = 173 K

0.27 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.565, T max = 0.648

12825 measured reflections

3297 independent reflections

2990 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.11

3297 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −1.56 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024931/cs2129sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024931/cs2129Isup2.hkl

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

C15H10FIO2S	F(000) = 776
Mr = 400.19	Dx = 1.861 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8763 reflections
a = 13.1665 (4) Å	θ = 2.4–27.6°
b = 11.4338 (4) Å	µ = 2.40 mm−1
c = 9.9296 (3) Å	T = 173 K
β = 107.181 (1)°	Block, colourless
V = 1428.13 (8) Å3	0.27 × 0.24 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3297 independent reflections
Radiation source: rotating anode	2990 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.6°
φ and ω scans	h = −15→17
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.565, Tmax = 0.648	l = −12→12
12825 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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F2) = 0.077	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0381P)2 + 1.2193P] where P = (Fo2 + 2Fc2)/3
3297 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −1.56 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
I	0.774810 (15)	0.162106 (16)	0.53507 (2)	0.03259 (8)
S	0.70499 (5)	0.67499 (6)	0.22747 (6)	0.02368 (14)
F	0.31812 (15)	0.49689 (19)	0.3339 (2)	0.0480 (5)
O1	0.94047 (15)	0.67042 (15)	0.57609 (19)	0.0249 (4)
O2	0.71831 (16)	0.60325 (19)	0.10757 (19)	0.0318 (4)
C1	0.8028 (2)	0.6377 (2)	0.3837 (2)	0.0213 (5)
C2	0.82677 (18)	0.5281 (2)	0.4598 (2)	0.0195 (5)
C3	0.78672 (19)	0.4142 (2)	0.4425 (2)	0.0219 (5)
H3	0.7309	0.3931	0.3643	0.026*
C4	0.8338 (2)	0.3340 (2)	0.5469 (3)	0.0233 (5)
C5	0.9195 (2)	0.3625 (2)	0.6643 (3)	0.0263 (5)
H5	0.9488	0.3058	0.7318	0.032*
C6	0.9608 (2)	0.4746 (2)	0.6804 (3)	0.0259 (5)
H6	1.0184	0.4951	0.7567	0.031*
C7	0.91229 (19)	0.5544 (2)	0.5777 (2)	0.0214 (5)
C8	0.8732 (2)	0.7187 (2)	0.4571 (3)	0.0229 (5)
C9	0.8903 (2)	0.8441 (2)	0.4345 (3)	0.0292 (6)
H9A	0.8451	0.8675	0.3436	0.044*
H9B	0.9632	0.8567	0.4387	0.044*
H9C	0.8735	0.8896	0.5064	0.044*
C10	0.59180 (19)	0.6152 (2)	0.2691 (2)	0.0226 (5)
C11	0.5564 (2)	0.6657 (2)	0.3746 (3)	0.0298 (6)
H11	0.5945	0.7263	0.4293	0.036*
C12	0.4639 (2)	0.6250 (3)	0.3973 (3)	0.0330 (6)
H12	0.4393	0.6570	0.4679	0.040*
C13	0.4092 (2)	0.5362 (3)	0.3133 (3)	0.0310 (6)
C14	0.4427 (2)	0.4850 (3)	0.2094 (3)	0.0315 (6)
H14	0.4039	0.4247	0.1549	0.038*
C15	0.5360 (2)	0.5251 (2)	0.1870 (3)	0.0267 (5)
H15	0.5607	0.4916	0.1173	0.032*

	U11	U22	U33	U12	U13	U23
I	0.03251 (12)	0.02096 (12)	0.04268 (13)	0.00056 (6)	0.00859 (9)	0.00097 (7)
S	0.0267 (3)	0.0237 (3)	0.0189 (3)	0.0016 (2)	0.0038 (2)	0.0032 (2)
F	0.0320 (9)	0.0613 (13)	0.0562 (11)	−0.0066 (9)	0.0216 (8)	−0.0055 (10)
O1	0.0236 (9)	0.0244 (10)	0.0240 (8)	−0.0017 (7)	0.0031 (7)	−0.0028 (7)
O2	0.0364 (10)	0.0411 (12)	0.0203 (8)	−0.0014 (9)	0.0122 (8)	−0.0030 (8)
C1	0.0214 (11)	0.0211 (12)	0.0208 (11)	0.0004 (9)	0.0056 (9)	0.0009 (9)
C2	0.0191 (11)	0.0211 (12)	0.0182 (10)	0.0021 (9)	0.0055 (8)	0.0003 (9)
C3	0.0219 (11)	0.0216 (12)	0.0208 (11)	0.0012 (9)	0.0043 (9)	−0.0012 (9)
C4	0.0250 (12)	0.0193 (13)	0.0258 (12)	0.0005 (9)	0.0079 (10)	−0.0022 (9)
C5	0.0293 (13)	0.0265 (13)	0.0215 (11)	0.0076 (11)	0.0050 (10)	0.0024 (10)
C6	0.0243 (12)	0.0286 (14)	0.0206 (11)	0.0034 (10)	0.0004 (9)	−0.0028 (10)
C7	0.0206 (11)	0.0230 (12)	0.0207 (10)	0.0009 (9)	0.0064 (9)	−0.0027 (9)
C8	0.0231 (12)	0.0247 (13)	0.0220 (11)	0.0013 (10)	0.0085 (9)	−0.0013 (9)
C9	0.0294 (14)	0.0238 (14)	0.0353 (14)	−0.0034 (10)	0.0111 (11)	−0.0010 (10)
C10	0.0234 (12)	0.0233 (13)	0.0183 (10)	0.0050 (10)	0.0017 (9)	0.0027 (9)
C11	0.0339 (15)	0.0285 (15)	0.0256 (12)	0.0020 (11)	0.0067 (11)	−0.0051 (10)
C12	0.0354 (15)	0.0368 (16)	0.0295 (13)	0.0068 (13)	0.0138 (11)	−0.0024 (12)
C13	0.0221 (12)	0.0380 (16)	0.0324 (13)	0.0038 (11)	0.0074 (10)	0.0035 (12)
C14	0.0272 (13)	0.0327 (15)	0.0319 (13)	−0.0027 (11)	0.0045 (11)	−0.0071 (11)
C15	0.0260 (12)	0.0295 (14)	0.0225 (11)	0.0034 (10)	0.0039 (10)	−0.0049 (10)

I—C4	2.104 (2)	C6—C7	1.376 (4)
I—O2i	3.255 (2)	C6—H6	0.9300
S—O2	1.4981 (19)	C8—C9	1.478 (4)
S—C1	1.751 (2)	C9—H9A	0.9600
S—C10	1.795 (3)	C9—H9B	0.9600
F—C13	1.351 (3)	C9—H9C	0.9600
O1—C8	1.366 (3)	C10—C15	1.383 (4)
O1—C7	1.379 (3)	C10—C11	1.391 (4)
C1—C8	1.360 (4)	C11—C12	1.383 (4)
C1—C2	1.449 (3)	C11—H11	0.9300
C2—C3	1.396 (3)	C12—C13	1.375 (4)
C2—C7	1.396 (3)	C12—H12	0.9300
C3—C4	1.386 (3)	C13—C14	1.368 (4)
C3—H3	0.9300	C14—C15	1.389 (4)
C4—C5	1.401 (4)	C14—H14	0.9300
C5—C6	1.383 (4)	C15—H15	0.9300
C5—H5	0.9300
C4—I—O2i	164.42 (8)	C1—C8—C9	133.5 (2)
O2—S—C1	110.03 (12)	O1—C8—C9	115.8 (2)
O2—S—C10	105.95 (12)	C8—C9—H9A	109.5
C1—S—C10	98.44 (11)	C8—C9—H9B	109.5
C8—O1—C7	106.94 (19)	H9A—C9—H9B	109.5
C8—C1—C2	107.5 (2)	C8—C9—H9C	109.5
C8—C1—S	121.0 (2)	H9A—C9—H9C	109.5
C2—C1—S	131.48 (19)	H9B—C9—H9C	109.5
C3—C2—C7	119.1 (2)	C15—C10—C11	121.0 (3)
C3—C2—C1	136.5 (2)	C15—C10—S	118.73 (19)
C7—C2—C1	104.4 (2)	C11—C10—S	120.1 (2)
C4—C3—C2	117.1 (2)	C12—C11—C10	119.3 (3)
C4—C3—H3	121.4	C12—C11—H11	120.3
C2—C3—H3	121.4	C10—C11—H11	120.3
C3—C4—C5	122.8 (2)	C13—C12—C11	118.6 (3)
C3—C4—I	120.02 (19)	C13—C12—H12	120.7
C5—C4—I	117.21 (19)	C11—C12—H12	120.7
C6—C5—C4	120.3 (2)	F—C13—C14	118.1 (3)
C6—C5—H5	119.9	F—C13—C12	118.9 (3)
C4—C5—H5	119.9	C14—C13—C12	123.0 (3)
C7—C6—C5	116.6 (2)	C13—C14—C15	118.5 (3)
C7—C6—H6	121.7	C13—C14—H14	120.8
C5—C6—H6	121.7	C15—C14—H14	120.8
C6—C7—O1	125.4 (2)	C10—C15—C14	119.5 (2)
C6—C7—C2	124.1 (2)	C10—C15—H15	120.2
O1—C7—C2	110.5 (2)	C14—C15—H15	120.2
C1—C8—O1	110.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ii	0.93	2.55	3.472 (3)	170
C9—H9C···O2iii	0.96	2.53	3.277 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.55	3.472 (3)	170
C9—H9C⋯O2ii	0.96	2.53	3.277 (3)	135

Symmetry codes: (i) ; (ii) .