5-Iodo-7-methyl-3-methyl-sulfinyl-2-phenyl-1-benzofuran.

The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 5-iodo-7-methyl-3-methyl-sulfanyl-2-phenyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 27.17 (9)° with the plane of the benzofuran fragment, with the O atom and the methyl group of the methyl-sulfinyl substituent lying on opposite sides of this plane. The crystal structure exhibits inter-molecular C-H⋯I inter-actions, and an I⋯O halogen bond of 3.107 (2) Å with a nearly linear C-I⋯O angle of 173.73 (6)°.

Related literature

For the crystal structures of similar 5-halo-3-methyl­sulfinyl-2-phenyl-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 = 10.385 (5) Å

b = 17.174 (8) Å

c = 8.943 (4) Å

β = 112.847 (7)°

V = 1469.9 (12) Å3

Z = 4

Mo Kα radiation

μ = 2.32 mm−1

T = 173 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.572, T max = 0.623

11429 measured reflections

2877 independent reflections

2706 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.053

S = 1.06

2877 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.66 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536808014694/zl2118sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014694/zl2118Isup2.hkl

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

C16H13IO2S	F000 = 776
Mr = 396.22	Dx = 1.790 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9956 reflections
a = 10.385 (5) Å	θ = 2.1–28.4º
b = 17.174 (8) Å	µ = 2.32 mm−1
c = 8.943 (4) Å	T = 173 (2) K
β = 112.847 (7)º	Block, colorless
V = 1469.9 (12) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	2877 independent reflections
Radiation source: fine-focus sealed tube	2706 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 173(2) K	θmin = 2.4º
φ and ω scans	h = −12→12
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	k = −21→21
Tmin = 0.572, Tmax = 0.623	l = −11→11
11429 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)] = 0.020	H-atom parameters constrained
wR(F2) = 0.053	w = 1/[σ2(Fo2) + (0.0278P)2 + 0.8832P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2877 reflections	Δρmax = 0.39 e Å−3
183 parameters	Δρmin = −0.66 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	−0.043288 (13)	0.558358 (8)	0.210981 (16)	0.02333 (7)
S	0.36162 (5)	0.29269 (3)	0.14788 (6)	0.02051 (11)
O1	0.50724 (14)	0.38231 (8)	0.59241 (16)	0.0184 (3)
O2	0.30733 (17)	0.35243 (9)	0.01551 (18)	0.0280 (3)
C1	0.3955 (2)	0.34115 (11)	0.3340 (2)	0.0186 (4)
C2	0.3154 (2)	0.40433 (12)	0.3616 (2)	0.0185 (4)
C3	0.1901 (2)	0.44237 (11)	0.2685 (3)	0.0199 (4)
H3	0.1385	0.4291	0.1581	0.024*
C4	0.1451 (2)	0.50027 (12)	0.3454 (2)	0.0203 (4)
C5	0.2211 (2)	0.52118 (12)	0.5084 (2)	0.0211 (4)
H5	0.1866	0.5614	0.5556	0.025*
C6	0.3460 (2)	0.48423 (11)	0.6021 (2)	0.0195 (4)
C7	0.3883 (2)	0.42659 (12)	0.5218 (2)	0.0182 (4)
C8	0.5095 (2)	0.32999 (11)	0.4756 (2)	0.0180 (4)
C9	0.6257 (2)	0.27448 (12)	0.5307 (2)	0.0184 (4)
C10	0.7494 (2)	0.29442 (13)	0.6599 (3)	0.0267 (5)
H10	0.7591	0.3445	0.7082	0.032*
C11	0.8579 (2)	0.24128 (14)	0.7177 (3)	0.0357 (6)
H11	0.9417	0.2550	0.8061	0.043*
C12	0.8452 (2)	0.16800 (14)	0.6474 (3)	0.0333 (5)
H12	0.9199	0.1317	0.6875	0.040*
C13	0.7229 (2)	0.14820 (13)	0.5185 (3)	0.0284 (5)
H13	0.7144	0.0984	0.4693	0.034*
C14	0.6129 (2)	0.20047 (12)	0.4608 (3)	0.0242 (4)
H14	0.5287	0.1861	0.3738	0.029*
C15	0.4267 (2)	0.50275 (13)	0.7788 (3)	0.0265 (5)
H15A	0.4092	0.4624	0.8460	0.040*
H15B	0.3967	0.5534	0.8043	0.040*
H15C	0.5268	0.5046	0.8010	0.040*
C16	0.2127 (2)	0.23678 (14)	0.1402 (3)	0.0310 (5)
H16A	0.1375	0.2721	0.1369	0.046*
H16B	0.2391	0.2037	0.2369	0.046*
H16C	0.1803	0.2041	0.0428	0.046*

	U11	U22	U33	U12	U13	U23
I	0.01881 (9)	0.02267 (10)	0.02713 (10)	0.00497 (5)	0.00739 (7)	0.00177 (5)
S	0.0221 (3)	0.0235 (3)	0.0161 (2)	0.0048 (2)	0.00748 (19)	−0.00083 (18)
O1	0.0190 (7)	0.0184 (7)	0.0170 (6)	0.0028 (5)	0.0060 (6)	−0.0001 (5)
O2	0.0330 (9)	0.0325 (8)	0.0175 (7)	0.0065 (7)	0.0088 (6)	0.0050 (6)
C1	0.0197 (9)	0.0193 (10)	0.0179 (9)	0.0009 (8)	0.0084 (8)	−0.0004 (7)
C2	0.0194 (9)	0.0184 (9)	0.0193 (9)	0.0006 (8)	0.0094 (8)	0.0015 (7)
C3	0.0199 (10)	0.0203 (10)	0.0187 (10)	0.0017 (8)	0.0067 (8)	0.0017 (7)
C4	0.0170 (9)	0.0227 (10)	0.0215 (10)	0.0023 (8)	0.0077 (8)	0.0038 (8)
C5	0.0248 (10)	0.0186 (10)	0.0226 (10)	0.0023 (8)	0.0123 (9)	−0.0007 (8)
C6	0.0233 (10)	0.0180 (9)	0.0193 (10)	−0.0003 (8)	0.0105 (8)	0.0006 (7)
C7	0.0185 (10)	0.0169 (9)	0.0194 (10)	−0.0004 (8)	0.0075 (8)	0.0025 (7)
C8	0.0205 (10)	0.0174 (9)	0.0181 (9)	−0.0016 (8)	0.0096 (8)	−0.0008 (7)
C9	0.0177 (9)	0.0206 (10)	0.0186 (9)	0.0003 (8)	0.0090 (8)	0.0040 (7)
C10	0.0219 (11)	0.0215 (10)	0.0324 (12)	−0.0011 (9)	0.0057 (9)	−0.0006 (9)
C11	0.0186 (11)	0.0308 (12)	0.0452 (14)	0.0026 (9)	−0.0013 (10)	0.0021 (10)
C12	0.0233 (11)	0.0274 (12)	0.0478 (14)	0.0080 (9)	0.0121 (11)	0.0091 (10)
C13	0.0324 (12)	0.0209 (10)	0.0338 (12)	0.0036 (9)	0.0150 (10)	0.0013 (9)
C14	0.0251 (11)	0.0232 (10)	0.0234 (10)	0.0010 (9)	0.0086 (9)	−0.0003 (8)
C15	0.0320 (12)	0.0269 (11)	0.0190 (10)	0.0020 (9)	0.0080 (9)	−0.0031 (8)
C16	0.0315 (12)	0.0311 (12)	0.0278 (11)	−0.0070 (10)	0.0087 (10)	−0.0055 (9)

I—C4	2.107 (2)	C8—C9	1.465 (3)
I—O2i	3.107 (2)	C9—C10	1.396 (3)
S—O2	1.501 (2)	C9—C14	1.400 (3)
S—C1	1.770 (2)	C10—C11	1.385 (3)
S—C16	1.799 (2)	C10—H10	0.9500
O1—C7	1.377 (2)	C11—C12	1.390 (4)
O1—C8	1.385 (2)	C11—H11	0.9500
C1—C8	1.370 (3)	C12—C13	1.386 (3)
C1—C2	1.446 (3)	C12—H12	0.9500
C2—C7	1.389 (3)	C13—C14	1.385 (3)
C2—C3	1.404 (3)	C13—H13	0.9500
C3—C4	1.389 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.409 (3)	C15—H15B	0.9800
C5—C6	1.394 (3)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.391 (3)	C16—H16B	0.9800
C6—C15	1.507 (3)	C16—H16C	0.9800
C4—I—O2i	173.73 (6)	C10—C9—C8	119.45 (19)
O2—S—C1	107.27 (10)	C14—C9—C8	121.16 (18)
O2—S—C16	106.30 (11)	C11—C10—C9	120.1 (2)
C1—S—C16	98.10 (10)	C11—C10—H10	120.0
C7—O1—C8	106.69 (15)	C9—C10—H10	120.0
C8—C1—C2	107.15 (17)	C10—C11—C12	120.5 (2)
C8—C1—S	126.05 (16)	C10—C11—H11	119.8
C2—C1—S	126.59 (15)	C12—C11—H11	119.8
C7—C2—C3	119.48 (19)	C13—C12—C11	119.6 (2)
C7—C2—C1	105.27 (17)	C13—C12—H12	120.2
C3—C2—C1	135.23 (19)	C11—C12—H12	120.2
C4—C3—C2	116.85 (19)	C14—C13—C12	120.5 (2)
C4—C3—H3	121.6	C14—C13—H13	119.7
C2—C3—H3	121.6	C12—C13—H13	119.7
C3—C4—C5	122.24 (19)	C13—C14—C9	120.0 (2)
C3—C4—I	118.20 (15)	C13—C14—H14	120.0
C5—C4—I	119.56 (15)	C9—C14—H14	120.0
C6—C5—C4	121.56 (19)	C6—C15—H15A	109.5
C6—C5—H5	119.2	C6—C15—H15B	109.5
C4—C5—H5	119.2	H15A—C15—H15B	109.5
C5—C6—C7	114.84 (18)	C6—C15—H15C	109.5
C5—C6—C15	122.91 (19)	H15A—C15—H15C	109.5
C7—C6—C15	122.21 (19)	H15B—C15—H15C	109.5
O1—C7—C2	110.71 (17)	S—C16—H16A	109.5
O1—C7—C6	124.27 (18)	S—C16—H16B	109.5
C2—C7—C6	125.00 (19)	H16A—C16—H16B	109.5
C1—C8—O1	110.17 (17)	S—C16—H16C	109.5
C1—C8—C9	134.83 (18)	H16A—C16—H16C	109.5
O1—C8—C9	114.93 (16)	H16B—C16—H16C	109.5
C10—C9—C14	119.33 (19)
O2—S—C1—C8	−138.12 (18)	C5—C6—C7—O1	−179.08 (18)
C16—S—C1—C8	111.9 (2)	C15—C6—C7—O1	−1.3 (3)
O2—S—C1—C2	36.1 (2)	C5—C6—C7—C2	−0.8 (3)
C16—S—C1—C2	−73.9 (2)	C15—C6—C7—C2	176.9 (2)
C8—C1—C2—C7	−0.4 (2)	C2—C1—C8—O1	0.0 (2)
S—C1—C2—C7	−175.49 (15)	S—C1—C8—O1	175.08 (14)
C8—C1—C2—C3	−179.1 (2)	C2—C1—C8—C9	176.7 (2)
S—C1—C2—C3	5.9 (3)	S—C1—C8—C9	−8.2 (3)
C7—C2—C3—C4	−1.1 (3)	C7—O1—C8—C1	0.5 (2)
C1—C2—C3—C4	177.4 (2)	C7—O1—C8—C9	−176.98 (16)
C2—C3—C4—C5	0.8 (3)	C1—C8—C9—C10	157.6 (2)
C2—C3—C4—I	−179.53 (14)	O1—C8—C9—C10	−25.8 (3)
C3—C4—C5—C6	−0.5 (3)	C1—C8—C9—C14	−25.2 (3)
I—C4—C5—C6	179.82 (15)	O1—C8—C9—C14	151.38 (18)
C4—C5—C6—C7	0.5 (3)	C14—C9—C10—C11	0.0 (3)
C4—C5—C6—C15	−177.3 (2)	C8—C9—C10—C11	177.3 (2)
C8—O1—C7—C2	−0.7 (2)	C9—C10—C11—C12	0.4 (4)
C8—O1—C7—C6	177.71 (19)	C10—C11—C12—C13	0.0 (4)
C3—C2—C7—O1	179.63 (17)	C11—C12—C13—C14	−0.8 (4)
C1—C2—C7—O1	0.7 (2)	C12—C13—C14—C9	1.2 (3)
C3—C2—C7—C6	1.2 (3)	C10—C9—C14—C13	−0.8 (3)
C1—C2—C7—C6	−177.73 (19)	C8—C9—C14—C13	−178.01 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Ii	0.95	3.06	3.954 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Ii	0.95	3.06	3.954 (3)	157

Symmetry code: (i) .