5-Iodo-2,7-dimethyl-3-phenyl-sulfinyl-1-benzofuran.

The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenyl-sulfanyl-1-benzofuran using 3-chloro-perbenzoic acid. The O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The phenyl ring is nearly perpendicular to the plane of the benzofuran fragment [89.15 (5)°]. The crystal structure is stabilized by an I⋯O halogen bond [I⋯O = 3.177 (2) Å and C-I⋯O = 175.68 (6)°] linking mol-ecules into centrosymmetric dimers and by a weak C-H⋯π inter-action between a phenyl H atom and the furan ring of the benzofuran system.

Related literature

For the crystal structures of similar 5-iodo-2-methyl-1-benzofuran compounds, see: Choi et al. (2007a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H13IO2S

M = 396.22

Monoclinic,

a = 24.4683 (8) Å

b = 8.1686 (3) Å

c = 16.2345 (5) Å

β = 113.015 (1)°

V = 2986.54 (17) Å3

Z = 8

Mo Kα radiation

μ = 2.28 mm−1

T = 173 (2) K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.412, T max = 0.640

8756 measured reflections

3261 independent reflections

3063 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.053

S = 1.17

3261 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.80 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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/S1600536808001797/gk2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001797/gk2130Isup2.hkl

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

C16H13IO2S	F000 = 1552
Mr = 396.22	Dx = 1.762 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7108 reflections
a = 24.4683 (8) Å	θ = 2.6–28.3º
b = 8.1686 (3) Å	µ = 2.28 mm−1
c = 16.2345 (5) Å	T = 173 (2) K
β = 113.015 (1)º	Block, colorless
V = 2986.54 (17) Å3	0.40 × 0.40 × 0.20 mm
Z = 8

Bruker SMART CCD diffractometer	3261 independent reflections
Radiation source: fine-focus sealed tube	3063 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.013
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 173(2) K	θmin = 2.7º
φ and ω scans	h = −30→31
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	k = −10→6
Tmin = 0.412, Tmax = 0.640	l = −20→20
8756 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H-atom parameters constrained
wR(F2) = 0.053	w = 1/[σ2(Fo2) + (0.0277P)2 + 2.4985P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max < 0.001
3261 reflections	Δρmax = 0.29 e Å−3
183 parameters	Δρmin = −0.80 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	−0.081673 (5)	−0.158666 (17)	0.292529 (8)	0.02880 (6)
S	0.20287 (2)	−0.04894 (6)	0.48963 (3)	0.02319 (10)
O1	0.13474 (6)	−0.23728 (17)	0.65079 (9)	0.0242 (3)
O2	0.18514 (7)	−0.13130 (18)	0.40076 (10)	0.0307 (3)
C1	0.15689 (8)	−0.1211 (2)	0.54224 (13)	0.0217 (4)
C2	0.09364 (8)	−0.1507 (2)	0.50573 (13)	0.0208 (4)
C3	0.04657 (8)	−0.1279 (2)	0.42283 (13)	0.0232 (4)
H3	0.0524	−0.0787	0.3738	0.028*
C4	−0.00869 (9)	−0.1805 (2)	0.41583 (13)	0.0246 (4)
C5	−0.01857 (9)	−0.2510 (3)	0.48745 (13)	0.0279 (4)
H5	−0.0576	−0.2842	0.4791	0.034*
C6	0.02741 (9)	−0.2734 (3)	0.57055 (13)	0.0269 (4)
C7	0.08257 (8)	−0.2231 (2)	0.57559 (12)	0.0220 (4)
C8	0.17897 (9)	−0.1754 (2)	0.62816 (13)	0.0235 (4)
C9	0.17569 (8)	0.1567 (2)	0.46631 (14)	0.0227 (4)
C10	0.16105 (9)	0.2173 (3)	0.38100 (14)	0.0277 (4)
H10	0.1614	0.1477	0.3343	0.033*
C11	0.14575 (10)	0.3820 (3)	0.36411 (16)	0.0340 (5)
H11	0.1354	0.4249	0.3055	0.041*
C12	0.14560 (9)	0.4826 (3)	0.43195 (17)	0.0357 (5)
H12	0.1352	0.5947	0.4201	0.043*
C13	0.16055 (10)	0.4211 (3)	0.51723 (17)	0.0357 (5)
H13	0.1601	0.4913	0.5636	0.043*
C14	0.17623 (9)	0.2583 (3)	0.53581 (14)	0.0281 (4)
H14	0.1871	0.2165	0.5947	0.034*
C15	0.01764 (11)	−0.3447 (3)	0.64905 (16)	0.0429 (6)
H15A	0.0377	−0.4508	0.6647	0.064*
H15B	−0.0250	−0.3595	0.6333	0.064*
H15C	0.0338	−0.2702	0.7003	0.064*
C16	0.23960 (9)	−0.1798 (3)	0.69950 (14)	0.0317 (5)
H16A	0.2685	−0.1459	0.6747	0.048*
H16B	0.2487	−0.2914	0.7231	0.048*
H16C	0.2417	−0.1052	0.7479	0.048*

	U11	U22	U33	U12	U13	U23
I	0.02196 (8)	0.03709 (9)	0.02313 (8)	0.00094 (5)	0.00425 (6)	0.00074 (5)
S	0.0188 (2)	0.0262 (2)	0.0266 (2)	0.00015 (17)	0.01100 (18)	−0.00063 (18)
O1	0.0225 (6)	0.0283 (7)	0.0211 (6)	0.0003 (5)	0.0079 (5)	0.0015 (5)
O2	0.0394 (8)	0.0282 (7)	0.0312 (8)	−0.0009 (6)	0.0210 (7)	−0.0059 (6)
C1	0.0205 (9)	0.0227 (9)	0.0224 (9)	0.0012 (7)	0.0090 (7)	−0.0004 (7)
C2	0.0201 (9)	0.0212 (9)	0.0225 (9)	0.0011 (7)	0.0100 (7)	−0.0011 (7)
C3	0.0233 (9)	0.0262 (10)	0.0207 (9)	0.0017 (7)	0.0092 (7)	0.0022 (7)
C4	0.0217 (9)	0.0288 (10)	0.0212 (9)	0.0021 (7)	0.0060 (7)	−0.0005 (7)
C5	0.0205 (9)	0.0375 (11)	0.0267 (10)	−0.0033 (8)	0.0102 (8)	−0.0005 (8)
C6	0.0260 (10)	0.0324 (10)	0.0241 (9)	−0.0027 (8)	0.0118 (8)	0.0008 (8)
C7	0.0225 (9)	0.0240 (9)	0.0194 (8)	0.0020 (7)	0.0082 (7)	−0.0002 (7)
C8	0.0219 (9)	0.0238 (9)	0.0246 (9)	0.0008 (7)	0.0090 (8)	−0.0033 (7)
C9	0.0161 (8)	0.0234 (9)	0.0295 (10)	−0.0043 (7)	0.0101 (7)	−0.0038 (7)
C10	0.0275 (10)	0.0283 (10)	0.0266 (10)	−0.0060 (8)	0.0099 (8)	−0.0043 (8)
C11	0.0279 (10)	0.0316 (11)	0.0369 (12)	−0.0067 (9)	0.0066 (9)	0.0046 (9)
C12	0.0272 (10)	0.0233 (10)	0.0561 (14)	−0.0050 (8)	0.0156 (10)	−0.0013 (9)
C13	0.0333 (11)	0.0303 (11)	0.0497 (13)	−0.0085 (9)	0.0230 (10)	−0.0144 (10)
C14	0.0274 (10)	0.0305 (11)	0.0290 (10)	−0.0073 (8)	0.0138 (8)	−0.0077 (8)
C15	0.0319 (12)	0.0681 (18)	0.0300 (12)	−0.0089 (11)	0.0136 (10)	0.0117 (11)
C16	0.0237 (10)	0.0408 (12)	0.0258 (10)	0.0015 (8)	0.0044 (8)	0.0007 (8)

I—C4	2.105 (2)	C8—C16	1.483 (3)
I—O2i	3.177 (2)	C9—C10	1.380 (3)
S—O2	1.494 (2)	C9—C14	1.397 (3)
S—C1	1.759 (2)	C10—C11	1.394 (3)
S—C9	1.791 (2)	C10—H10	0.9500
O1—C8	1.369 (2)	C11—C12	1.375 (3)
O1—C7	1.384 (2)	C11—H11	0.9500
C1—C8	1.358 (3)	C12—C13	1.381 (3)
C1—C2	1.445 (3)	C12—H12	0.9500
C2—C7	1.396 (3)	C13—C14	1.384 (3)
C2—C3	1.400 (3)	C13—H13	0.9500
C3—C4	1.381 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.400 (3)	C15—H15B	0.9800
C5—C6	1.390 (3)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.382 (3)	C16—H16B	0.9800
C6—C15	1.503 (3)	C16—H16C	0.9800
C4—I—O2i	175.68 (6)	C6—C7—C2	125.0 (2)
O2—S—C1	108.58 (9)	O1—C7—C2	110.3 (2)
O2—S—C9	105.92 (9)	C1—C8—O1	111.0 (2)
C1—S—C9	99.30 (9)	C1—C8—C16	133.2 (2)
C8—O1—C7	106.6 (1)	O1—C8—C16	115.8 (2)
C8—C1—C2	107.4 (2)	C10—C9—C14	120.9 (2)
C8—C1—S	122.3 (2)	C10—C9—S	118.6 (2)
C2—C1—S	130.0 (2)	C14—C9—S	120.1 (2)
C7—C2—C3	119.3 (2)	C9—C10—C11	119.2 (2)
C7—C2—C1	104.7 (2)	C12—C11—C10	120.2 (2)
C3—C2—C1	136.0 (2)	C11—C12—C13	120.2 (2)
C4—C3—C2	116.7 (2)	C12—C13—C14	120.7 (2)
C3—C4—C5	122.8 (2)	C13—C14—C9	118.7 (2)
C3—C4—I	119.4 (1)	H15A—C15—H15B	109.5
C5—C4—I	117.8 (1)	H15A—C15—H15C	109.5
C6—C5—C4	121.5 (2)	H15B—C15—H15C	109.5
C7—C6—C5	114.8 (2)	H16A—C16—H16B	109.5
C7—C6—C15	122.7 (2)	H16A—C16—H16C	109.5
C5—C6—C15	122.5 (2)	H16B—C16—H16C	109.5
C6—C7—O1	124.7 (2)
O2—S—C1—C8	130.7 (2)	C3—C2—C7—C6	−1.2 (3)
C9—S—C1—C8	−118.9 (2)	C1—C2—C7—C6	−179.7 (2)
O2—S—C1—C2	−42.4 (2)	C3—C2—C7—O1	178.9 (2)
C9—S—C1—C2	68.0 (2)	C1—C2—C7—O1	0.4 (2)
C8—C1—C2—C7	0.0 (2)	C2—C1—C8—O1	−0.5 (2)
S—C1—C2—C7	174.0 (2)	S—C1—C8—O1	−174.9 (1)
C8—C1—C2—C3	−178.1 (2)	C2—C1—C8—C16	179.7 (2)
S—C1—C2—C3	−4.1 (3)	S—C1—C8—C16	5.2 (3)
C7—C2—C3—C4	−0.3 (3)	C7—O1—C8—C1	0.7 (2)
C1—C2—C3—C4	177.6 (2)	C7—O1—C8—C16	−179.5 (2)
C2—C3—C4—C5	1.1 (3)	O2—S—C9—C10	−18.3 (2)
C2—C3—C4—I	−178.0 (1)	C1—S—C9—C10	−130.8 (2)
C3—C4—C5—C6	−0.5 (3)	O2—S—C9—C14	169.2 (2)
I—C4—C5—C6	178.5 (2)	C1—S—C9—C14	56.8 (2)
C4—C5—C6—C7	−0.8 (3)	C14—C9—C10—C11	−1.0 (3)
C4—C5—C6—C15	178.4 (2)	S—C9—C10—C11	−173.4 (2)
C5—C6—C7—O1	−178.4 (2)	C9—C10—C11—C12	0.3 (3)
C15—C6—C7—O1	2.4 (3)	C10—C11—C12—C13	0.0 (3)
C5—C6—C7—C2	1.7 (3)	C11—C12—C13—C14	0.4 (3)
C15—C6—C7—C2	−177.5 (2)	C12—C13—C14—C9	−1.1 (3)
C8—O1—C7—C6	179.40 (19)	C10—C9—C14—C13	1.3 (3)
C8—O1—C7—C2	−0.6 (2)	S—C9—C14—C13	173.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cgii	0.95	2.82	3.576 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯Cgi	0.95	2.82	3.576 (3)	137

Symmetry code: (i) .