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

In the title compound, C(16)H(13)IO(2)S, the 4-methyl-phenyl ring makes a dihedral angle of 88.36 (7)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds and an I⋯O contact [3.103 (2) Å]. The crystal structure also exhibits slipped π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.659 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2007 ▶, 2010 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H13IO2S

M = 396.22

Monoclinic,

a = 14.3793 (3) Å

b = 11.4519 (2) Å

c = 9.6419 (2) Å

β = 107.854 (1)°

V = 1511.27 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.26 mm−1

T = 173 K

0.22 × 0.20 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.638, T max = 0.846

13752 measured reflections

3490 independent reflections

2900 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.068

S = 1.05

3490 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −1.18 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/S1600536812030036/zl2489sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030036/zl2489Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030036/zl2489Isup3.cml

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

C16H13IO2S	F(000) = 776
Mr = 396.22	Dx = 1.741 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.3793 (3) Å	Cell parameters from 5240 reflections
b = 11.4519 (2) Å	θ = 2.9–27.5°
c = 9.6419 (2) Å	µ = 2.26 mm−1
β = 107.854 (1)°	T = 173 K
V = 1511.27 (5) Å3	Block, colourless
Z = 4	0.22 × 0.20 × 0.08 mm

Bruker SMART APEXII CCD diffractometer	3490 independent reflections
Radiation source: rotating anode	2900 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.033
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.5°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→12
Tmin = 0.638, Tmax = 0.846	l = −12→12
13752 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)] = 0.027	Hydrogen site location: difference Fourier map
wR(F2) = 0.068	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0302P)2 + 0.8945P] where P = (Fo2 + 2Fc2)/3
3490 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −1.18 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	0.790469 (12)	0.834779 (16)	0.53396 (2)	0.03646 (8)
S1	0.72860 (4)	0.32747 (6)	0.20862 (7)	0.02653 (14)
O1	0.94424 (12)	0.32924 (15)	0.57306 (19)	0.0278 (4)
O2	0.73517 (13)	0.41260 (17)	0.09476 (19)	0.0351 (4)
C1	0.81709 (16)	0.3620 (2)	0.3740 (3)	0.0250 (5)
C2	0.83857 (15)	0.4706 (2)	0.4533 (2)	0.0221 (5)
C3	0.80122 (16)	0.5838 (2)	0.4364 (3)	0.0252 (5)
H3	0.7477	0.6052	0.3546	0.030*
C4	0.84537 (17)	0.6639 (2)	0.5439 (3)	0.0267 (5)
C5	0.92529 (17)	0.6352 (2)	0.6641 (3)	0.0296 (6)
H5	0.9535	0.6931	0.7351	0.036*
C6	0.96359 (16)	0.5243 (2)	0.6807 (3)	0.0287 (5)
H6	1.0185	0.5038	0.7609	0.034*
C7	0.91797 (16)	0.4444 (2)	0.5747 (3)	0.0244 (5)
C8	0.88230 (16)	0.2815 (2)	0.4494 (3)	0.0260 (5)
C9	0.89775 (19)	0.1562 (2)	0.4262 (3)	0.0334 (6)
H9A	0.8788	0.1096	0.4985	0.050*
H9B	0.9669	0.1426	0.4368	0.050*
H9C	0.8578	0.1335	0.3281	0.050*
C10	0.62215 (16)	0.3666 (2)	0.2572 (3)	0.0256 (5)
C11	0.56470 (19)	0.4576 (3)	0.1886 (3)	0.0376 (6)
H11	0.5827	0.5034	0.1188	0.045*
C12	0.47984 (19)	0.4818 (3)	0.2227 (4)	0.0446 (7)
H12	0.4397	0.5448	0.1751	0.053*
C13	0.45216 (18)	0.4171 (3)	0.3234 (3)	0.0385 (7)
C14	0.5114 (2)	0.3241 (3)	0.3901 (3)	0.0419 (7)
H14	0.4933	0.2781	0.4597	0.050*
C15	0.59568 (18)	0.2975 (3)	0.3572 (3)	0.0342 (6)
H15	0.6350	0.2330	0.4021	0.041*
C16	0.3605 (2)	0.4459 (4)	0.3621 (4)	0.0579 (10)
H16A	0.3382	0.5244	0.3269	0.087*
H16B	0.3745	0.4429	0.4681	0.087*
H16C	0.3094	0.3890	0.3162	0.087*

	U11	U22	U33	U12	U13	U23
I1	0.04096 (11)	0.02548 (13)	0.04085 (12)	0.00036 (7)	0.00948 (8)	−0.00264 (7)
S1	0.0285 (3)	0.0261 (4)	0.0240 (3)	−0.0025 (2)	0.0065 (2)	−0.0035 (2)
O1	0.0247 (7)	0.0292 (11)	0.0284 (9)	0.0029 (7)	0.0063 (7)	0.0019 (7)
O2	0.0416 (10)	0.0375 (12)	0.0275 (9)	−0.0046 (8)	0.0127 (8)	0.0017 (8)
C1	0.0224 (10)	0.0279 (15)	0.0250 (12)	−0.0001 (9)	0.0077 (9)	−0.0026 (9)
C2	0.0185 (9)	0.0265 (14)	0.0221 (11)	−0.0019 (9)	0.0072 (8)	−0.0014 (9)
C3	0.0239 (10)	0.0255 (14)	0.0253 (12)	−0.0009 (9)	0.0063 (9)	0.0013 (9)
C4	0.0286 (11)	0.0228 (15)	0.0300 (13)	−0.0026 (9)	0.0105 (9)	0.0015 (10)
C5	0.0306 (11)	0.0314 (16)	0.0261 (13)	−0.0086 (10)	0.0076 (10)	−0.0033 (10)
C6	0.0238 (10)	0.0345 (16)	0.0247 (12)	−0.0039 (10)	0.0029 (9)	0.0026 (10)
C7	0.0215 (10)	0.0262 (14)	0.0268 (12)	−0.0002 (9)	0.0094 (9)	0.0018 (10)
C8	0.0251 (10)	0.0275 (15)	0.0283 (12)	−0.0005 (10)	0.0126 (9)	−0.0009 (10)
C9	0.0350 (12)	0.0272 (16)	0.0408 (15)	0.0028 (11)	0.0156 (11)	−0.0025 (11)
C10	0.0233 (10)	0.0251 (14)	0.0261 (12)	−0.0038 (9)	0.0041 (9)	−0.0014 (10)
C11	0.0337 (12)	0.0369 (18)	0.0401 (15)	0.0017 (11)	0.0081 (11)	0.0108 (12)
C12	0.0310 (13)	0.044 (2)	0.0555 (19)	0.0084 (12)	0.0079 (12)	0.0079 (14)
C13	0.0242 (11)	0.048 (2)	0.0411 (16)	−0.0088 (11)	0.0075 (11)	−0.0094 (13)
C14	0.0373 (14)	0.053 (2)	0.0364 (16)	−0.0125 (13)	0.0133 (12)	0.0012 (13)
C15	0.0333 (12)	0.0349 (17)	0.0324 (14)	−0.0026 (11)	0.0069 (11)	0.0055 (11)
C16	0.0314 (14)	0.079 (3)	0.065 (2)	−0.0055 (15)	0.0176 (14)	−0.0212 (19)

I1—C4	2.101 (2)	C8—C9	1.479 (4)
I1—O2i	3.1034 (19)	C9—H9A	0.9800
S1—O2	1.4927 (19)	C9—H9B	0.9800
S1—C1	1.753 (2)	C9—H9C	0.9800
S1—C10	1.790 (2)	C10—C11	1.367 (4)
O1—C8	1.365 (3)	C10—C15	1.388 (4)
O1—C7	1.374 (3)	C11—C12	1.385 (4)
C1—C8	1.356 (3)	C11—H11	0.9500
C1—C2	1.443 (3)	C12—C13	1.374 (4)
C2—C3	1.394 (3)	C12—H12	0.9500
C2—C7	1.394 (3)	C13—C14	1.391 (4)
C3—C4	1.384 (3)	C13—C16	1.512 (4)
C3—H3	0.9500	C14—C15	1.379 (4)
C4—C5	1.398 (3)	C14—H14	0.9500
C5—C6	1.374 (4)	C15—H15	0.9500
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.379 (3)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
C4—I1—O2i	166.89 (8)	C8—C9—H9B	109.5
O2—S1—C1	109.25 (11)	H9A—C9—H9B	109.5
O2—S1—C10	106.33 (12)	C8—C9—H9C	109.5
C1—S1—C10	98.38 (11)	H9A—C9—H9C	109.5
C8—O1—C7	106.66 (18)	H9B—C9—H9C	109.5
C8—C1—C2	107.5 (2)	C11—C10—C15	121.1 (2)
C8—C1—S1	121.6 (2)	C11—C10—S1	120.2 (2)
C2—C1—S1	130.84 (18)	C15—C10—S1	118.5 (2)
C3—C2—C7	119.0 (2)	C10—C11—C12	118.9 (3)
C3—C2—C1	136.7 (2)	C10—C11—H11	120.5
C7—C2—C1	104.3 (2)	C12—C11—H11	120.5
C4—C3—C2	117.2 (2)	C13—C12—C11	121.8 (3)
C4—C3—H3	121.4	C13—C12—H12	119.1
C2—C3—H3	121.4	C11—C12—H12	119.1
C3—C4—C5	122.5 (2)	C12—C13—C14	118.1 (3)
C3—C4—I1	120.21 (18)	C12—C13—C16	121.3 (3)
C5—C4—I1	117.30 (19)	C14—C13—C16	120.6 (3)
C6—C5—C4	120.8 (2)	C15—C14—C13	121.3 (3)
C6—C5—H5	119.6	C15—C14—H14	119.4
C4—C5—H5	119.6	C13—C14—H14	119.4
C5—C6—C7	116.4 (2)	C14—C15—C10	118.8 (3)
C5—C6—H6	121.8	C14—C15—H15	120.6
C7—C6—H6	121.8	C10—C15—H15	120.6
O1—C7—C6	125.1 (2)	C13—C16—H16A	109.5
O1—C7—C2	110.7 (2)	C13—C16—H16B	109.5
C6—C7—C2	124.1 (2)	H16A—C16—H16B	109.5
C1—C8—O1	110.8 (2)	C13—C16—H16C	109.5
C1—C8—C9	133.6 (2)	H16A—C16—H16C	109.5
O1—C8—C9	115.6 (2)	H16B—C16—H16C	109.5
C8—C9—H9A	109.5
O2—S1—C1—C8	−126.3 (2)	C3—C2—C7—C6	−0.6 (4)
C10—S1—C1—C8	123.1 (2)	C1—C2—C7—C6	179.3 (2)
O2—S1—C1—C2	51.9 (3)	C2—C1—C8—O1	0.6 (3)
C10—S1—C1—C2	−58.7 (2)	S1—C1—C8—O1	179.22 (16)
C8—C1—C2—C3	179.7 (3)	C2—C1—C8—C9	179.3 (3)
S1—C1—C2—C3	1.3 (4)	S1—C1—C8—C9	−2.1 (4)
C8—C1—C2—C7	−0.2 (3)	C7—O1—C8—C1	−0.8 (3)
S1—C1—C2—C7	−178.6 (2)	C7—O1—C8—C9	−179.8 (2)
C7—C2—C3—C4	−0.8 (3)	O2—S1—C10—C11	1.7 (2)
C1—C2—C3—C4	179.4 (3)	C1—S1—C10—C11	114.7 (2)
C2—C3—C4—C5	1.1 (4)	O2—S1—C10—C15	176.9 (2)
C2—C3—C4—I1	−177.11 (17)	C1—S1—C10—C15	−70.1 (2)
O2i—I1—C4—C3	159.7 (2)	C15—C10—C11—C12	1.4 (4)
O2i—I1—C4—C5	−18.6 (5)	S1—C10—C11—C12	176.4 (2)
C3—C4—C5—C6	−0.2 (4)	C10—C11—C12—C13	0.1 (5)
I1—C4—C5—C6	178.08 (19)	C11—C12—C13—C14	−0.9 (5)
C4—C5—C6—C7	−1.1 (4)	C11—C12—C13—C16	178.7 (3)
C8—O1—C7—C6	−179.0 (2)	C12—C13—C14—C15	0.3 (4)
C8—O1—C7—C2	0.7 (3)	C16—C13—C14—C15	−179.3 (3)
C5—C6—C7—O1	−178.9 (2)	C13—C14—C15—C10	1.1 (4)
C5—C6—C7—C2	1.5 (4)	C11—C10—C15—C14	−2.0 (4)
C3—C2—C7—O1	179.8 (2)	S1—C10—C15—C14	−177.1 (2)
C1—C2—C7—O1	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ii	0.95	2.52	3.459 (3)	170
C9—H9A···O2iii	0.98	2.52	3.325 (3)	139
C15—H15···O2iii	0.95	2.58	3.499 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.95	2.52	3.459 (3)	170
C9—H9A⋯O2ii	0.98	2.52	3.325 (3)	139
C15—H15⋯O2ii	0.95	2.58	3.499 (3)	162

Symmetry codes: (i) ; (ii) .