2-(4-Iodo-phen-yl)-5,7-dimethyl-3-methyl-sulfinyl-1-benzofuran.

The title compound, C(17)H(15)IO(2)S, was prepared by the oxidation of 2-(4-iodo-phen-yl)-5,7-dimethyl-3-methyl-sulfanyl-1-benzofuran using 3-chloro-peroxy-benzoic acid. The 4-iodo-phenyl ring makes a dihedral angle of 26.0 (1)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of this plane. The crystal structure is stabilized by inter- and intra-molecular C-H⋯O hydrogen bonds, and by an I⋯O halogen bond with an I⋯O distance of 3.145 (2) Å and a nearly linear C-I⋯O angle of 164.01 (9)°.

Related literature

For the crystal structures of similar 2-aryl-3-methyl­sulfinyl-1-benzofuran compounds, see: Choi et al. (2007a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H15IO2S

M = 410.25

Triclinic,

a = 8.6320 (9) Å

b = 8.917 (1) Å

c = 11.638 (1) Å

α = 94.580 (2)°

β = 100.949 (2)°

γ = 113.725 (2)°

V = 792.90 (14) Å3

Z = 2

Mo Kα radiation

μ = 2.15 mm−1

T = 293 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.594, T max = 0.647

6882 measured reflections

3408 independent reflections

3214 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.080

S = 1.22

3408 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.50 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 I, global. DOI: 10.1107/S1600536808014104/zl2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014104/zl2115Isup2.hkl

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

C17H15IO2S	Z = 2
Mr = 410.25	F000 = 404
Triclinic, P1	Dx = 1.718 Mg m−3
Hall symbol: -p_1	Melting point = 450–451 K
a = 8.6320 (9) Å	Mo Kα radiation λ = 0.71069 Å
b = 8.917 (1) Å	Cell parameters from 5631 reflections
c = 11.638 (1) Å	θ = 2.5–28.3º
α = 94.580 (2)º	µ = 2.15 mm−1
β = 100.949 (2)º	T = 293 (2) K
γ = 113.725 (2)º	Block, colorless
V = 792.90 (14) Å3	0.40 × 0.20 × 0.20 mm

Bruker SMART CCD diffractometer	3408 independent reflections
Radiation source: fine-focus sealed tube	3214 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 293(2) K	θmin = 1.8º
φ and ω scans	h = −11→10
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	k = −11→11
Tmin = 0.594, Tmax = 0.647	l = −14→14
6882 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)] = 0.025	H-atom parameters constrained
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0374P)2 + 0.4132P] where P = (Fo2 + 2Fc2)/3
S = 1.22	(Δ/σ)max = 0.001
3408 reflections	Δρmax = 0.50 e Å−3
192 parameters	Δρmin = −0.66 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	0.26443 (2)	0.23987 (2)	−0.006964 (16)	0.03233 (9)
S	0.10120 (10)	0.19886 (8)	0.60394 (7)	0.02931 (16)
O1	0.3173 (3)	0.6586 (2)	0.54519 (18)	0.0262 (4)
O2	0.2055 (3)	0.1813 (3)	0.7150 (2)	0.0374 (5)
C1	0.1717 (4)	0.4134 (3)	0.6002 (3)	0.0262 (6)
C2	0.2089 (4)	0.5443 (3)	0.6979 (3)	0.0259 (5)
C3	0.1802 (4)	0.5533 (4)	0.8114 (3)	0.0294 (6)
H3	0.1197	0.4569	0.8393	0.035*
C4	0.2430 (4)	0.7078 (4)	0.8822 (3)	0.0309 (6)
C5	0.3335 (4)	0.8521 (4)	0.8378 (3)	0.0307 (6)
H5	0.3738	0.9548	0.8862	0.037*
C6	0.3655 (4)	0.8489 (4)	0.7256 (3)	0.0282 (6)
C7	0.2995 (4)	0.6914 (3)	0.6586 (3)	0.0256 (6)
C8	0.2386 (4)	0.4876 (3)	0.5117 (3)	0.0256 (5)
C9	0.2460 (4)	0.4269 (3)	0.3936 (2)	0.0247 (5)
C10	0.1189 (4)	0.2744 (4)	0.3281 (3)	0.0286 (6)
H10	0.0280	0.2098	0.3599	0.034*
C11	0.1279 (4)	0.2191 (4)	0.2158 (3)	0.0292 (6)
H11	0.0438	0.1169	0.1728	0.035*
C12	0.2623 (4)	0.3162 (4)	0.1674 (3)	0.0268 (6)
C13	0.3902 (4)	0.4699 (4)	0.2319 (3)	0.0289 (6)
H13	0.4803	0.5348	0.1997	0.035*
C14	0.3811 (4)	0.5239 (3)	0.3437 (3)	0.0274 (6)
H14	0.4656	0.6259	0.3866	0.033*
C15	0.2162 (5)	0.7226 (5)	1.0062 (3)	0.0416 (8)
H15A	0.0937	0.6706	1.0029	0.062*
H15B	0.2633	0.8380	1.0409	0.062*
H15C	0.2745	0.6687	1.0538	0.062*
C16	0.4651 (4)	1.0036 (4)	0.6797 (3)	0.0387 (7)
H16A	0.3979	1.0671	0.6682	0.058*
H16B	0.4867	0.9730	0.6054	0.058*
H16C	0.5742	1.0693	0.7362	0.058*
C17	−0.1093 (4)	0.1531 (4)	0.6283 (4)	0.0471 (9)
H17A	−0.1675	0.0368	0.6314	0.071*
H17B	−0.1764	0.1801	0.5646	0.071*
H17C	−0.0976	0.2176	0.7022	0.071*

	U11	U22	U33	U12	U13	U23
I	0.03823 (13)	0.03425 (13)	0.02494 (12)	0.01616 (9)	0.00863 (8)	0.00135 (8)
S	0.0364 (4)	0.0219 (3)	0.0299 (4)	0.0120 (3)	0.0091 (3)	0.0058 (3)
O1	0.0313 (10)	0.0209 (9)	0.0256 (10)	0.0103 (8)	0.0077 (8)	0.0028 (8)
O2	0.0405 (12)	0.0360 (12)	0.0384 (13)	0.0193 (10)	0.0058 (10)	0.0135 (10)
C1	0.0298 (13)	0.0227 (13)	0.0263 (14)	0.0123 (11)	0.0052 (11)	0.0037 (11)
C2	0.0287 (13)	0.0234 (13)	0.0264 (14)	0.0126 (11)	0.0052 (11)	0.0045 (11)
C3	0.0312 (14)	0.0304 (14)	0.0289 (15)	0.0145 (12)	0.0085 (12)	0.0075 (12)
C4	0.0295 (14)	0.0385 (16)	0.0265 (15)	0.0166 (13)	0.0069 (11)	0.0027 (12)
C5	0.0298 (14)	0.0269 (14)	0.0318 (15)	0.0109 (12)	0.0050 (12)	−0.0023 (12)
C6	0.0240 (13)	0.0253 (13)	0.0339 (15)	0.0100 (11)	0.0068 (11)	0.0011 (11)
C7	0.0254 (13)	0.0250 (13)	0.0264 (14)	0.0117 (11)	0.0049 (11)	0.0031 (11)
C8	0.0260 (13)	0.0219 (13)	0.0269 (14)	0.0097 (10)	0.0032 (11)	0.0036 (11)
C9	0.0271 (13)	0.0237 (13)	0.0224 (13)	0.0114 (11)	0.0031 (10)	0.0042 (10)
C10	0.0275 (13)	0.0271 (14)	0.0272 (14)	0.0077 (11)	0.0060 (11)	0.0051 (11)
C11	0.0294 (14)	0.0248 (13)	0.0257 (14)	0.0067 (11)	0.0017 (11)	0.0000 (11)
C12	0.0299 (14)	0.0283 (14)	0.0233 (13)	0.0150 (11)	0.0038 (11)	0.0031 (11)
C13	0.0293 (14)	0.0277 (14)	0.0296 (15)	0.0109 (11)	0.0091 (12)	0.0069 (11)
C14	0.0276 (13)	0.0227 (13)	0.0271 (14)	0.0078 (11)	0.0037 (11)	0.0017 (11)
C15	0.0498 (19)	0.0454 (18)	0.0279 (17)	0.0184 (15)	0.0118 (15)	0.0014 (14)
C16	0.0398 (17)	0.0259 (15)	0.0469 (19)	0.0079 (13)	0.0182 (15)	0.0024 (14)
C17	0.0318 (16)	0.0336 (17)	0.076 (3)	0.0111 (14)	0.0151 (17)	0.0201 (18)

I—C12	2.094 (3)	C9—C10	1.396 (4)
I—O2i	3.145 (2)	C9—C14	1.404 (4)
S—O2	1.486 (2)	C10—C11	1.387 (4)
S—C1	1.766 (3)	C10—H10	0.9300
S—C17	1.780 (4)	C11—C12	1.390 (4)
O1—C7	1.379 (3)	C11—H11	0.9300
O1—C8	1.382 (3)	C12—C13	1.401 (4)
C1—C8	1.364 (4)	C13—C14	1.378 (4)
C1—C2	1.452 (4)	C13—H13	0.9300
C2—C3	1.391 (4)	C14—H14	0.9300
C2—C7	1.396 (4)	C15—H15A	0.9600
C3—C4	1.385 (4)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.409 (4)	C16—H16A	0.9600
C4—C15	1.508 (4)	C16—H16B	0.9600
C5—C6	1.385 (4)	C16—H16C	0.9600
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.385 (4)	C17—H17B	0.9600
C6—C16	1.505 (4)	C17—H17C	0.9600
C8—C9	1.459 (4)
C12—I—O2i	164.01 (9)	C11—C10—H10	119.9
O2—S—C1	107.81 (13)	C9—C10—H10	119.9
O2—S—C17	105.98 (17)	C10—C11—C12	120.1 (3)
C1—S—C17	99.04 (15)	C10—C11—H11	119.9
C7—O1—C8	106.5 (2)	C12—C11—H11	119.9
C8—C1—C2	107.5 (2)	C11—C12—C13	120.3 (3)
C8—C1—S	123.8 (2)	C11—C12—I	119.8 (2)
C2—C1—S	127.1 (2)	C13—C12—I	119.8 (2)
C3—C2—C7	119.0 (3)	C14—C13—C12	119.4 (3)
C3—C2—C1	136.5 (3)	C14—C13—H13	120.3
C7—C2—C1	104.5 (2)	C12—C13—H13	120.3
C4—C3—C2	119.1 (3)	C13—C14—C9	120.9 (3)
C4—C3—H3	120.5	C13—C14—H14	119.5
C2—C3—H3	120.5	C9—C14—H14	119.5
C3—C4—C5	119.4 (3)	C4—C15—H15A	109.5
C3—C4—C15	120.7 (3)	C4—C15—H15B	109.5
C5—C4—C15	119.9 (3)	H15A—C15—H15B	109.5
C6—C5—C4	123.4 (3)	C4—C15—H15C	109.5
C6—C5—H5	118.3	H15A—C15—H15C	109.5
C4—C5—H5	118.3	H15B—C15—H15C	109.5
C7—C6—C5	114.7 (3)	C6—C16—H16A	109.5
C7—C6—C16	122.2 (3)	C6—C16—H16B	109.5
C5—C6—C16	123.0 (3)	H16A—C16—H16B	109.5
O1—C7—C6	124.7 (3)	C6—C16—H16C	109.5
O1—C7—C2	110.9 (2)	H16A—C16—H16C	109.5
C6—C7—C2	124.4 (3)	H16B—C16—H16C	109.5
C1—C8—O1	110.5 (2)	S—C17—H17A	109.5
C1—C8—C9	134.5 (3)	S—C17—H17B	109.5
O1—C8—C9	115.0 (2)	H17A—C17—H17B	109.5
C10—C9—C14	119.2 (3)	S—C17—H17C	109.5
C10—C9—C8	121.0 (3)	H17A—C17—H17C	109.5
C14—C9—C8	119.8 (2)	H17B—C17—H17C	109.5
C11—C10—C9	120.1 (3)
O2—S—C1—C8	120.8 (3)	C1—C2—C7—O1	0.7 (3)
C17—S—C1—C8	−129.1 (3)	C3—C2—C7—C6	0.5 (4)
O2—S—C1—C2	−43.3 (3)	C1—C2—C7—C6	−178.1 (3)
C17—S—C1—C2	66.8 (3)	C2—C1—C8—O1	0.1 (3)
C8—C1—C2—C3	−178.7 (3)	S—C1—C8—O1	−166.67 (19)
S—C1—C2—C3	−12.5 (5)	C2—C1—C8—C9	179.4 (3)
C8—C1—C2—C7	−0.5 (3)	S—C1—C8—C9	12.6 (5)
S—C1—C2—C7	165.7 (2)	C7—O1—C8—C1	0.4 (3)
C7—C2—C3—C4	−0.3 (4)	C7—O1—C8—C9	−179.1 (2)
C1—C2—C3—C4	177.8 (3)	C1—C8—C9—C10	27.6 (5)
C2—C3—C4—C5	0.3 (4)	O1—C8—C9—C10	−153.1 (3)
C2—C3—C4—C15	−179.4 (3)	C1—C8—C9—C14	−153.4 (3)
C3—C4—C5—C6	−0.6 (5)	O1—C8—C9—C14	25.9 (4)
C15—C4—C5—C6	179.1 (3)	C14—C9—C10—C11	0.8 (4)
C4—C5—C6—C7	0.7 (4)	C8—C9—C10—C11	179.8 (3)
C4—C5—C6—C16	−178.9 (3)	C9—C10—C11—C12	−0.8 (4)
C8—O1—C7—C6	178.1 (3)	C10—C11—C12—C13	0.4 (4)
C8—O1—C7—C2	−0.7 (3)	C10—C11—C12—I	−175.5 (2)
C5—C6—C7—O1	−179.4 (3)	C11—C12—C13—C14	−0.1 (4)
C16—C6—C7—O1	0.2 (5)	I—C12—C13—C14	175.8 (2)
C5—C6—C7—C2	−0.7 (4)	C12—C13—C14—C9	0.2 (4)
C16—C6—C7—C2	178.9 (3)	C10—C9—C14—C13	−0.5 (4)
C3—C2—C7—O1	179.3 (2)	C8—C9—C14—C13	−179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O1	0.96	2.55	2.975 (4)	107
C16—H16A···O2ii	0.96	2.39	3.288 (4)	156
C17—H17B···O1iii	0.96	2.51	3.422 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O1	0.96	2.55	2.975 (4)	107
C16—H16A⋯O2i	0.96	2.39	3.288 (4)	156
C17—H17B⋯O1ii	0.96	2.51	3.422 (4)	159

Symmetry codes: (i) ; (ii) .