Isopropyl 2-(5-iodo-7-methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

In the title mol-ecule, C(15)H(17)IO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. In the crystal structure, inter-molecular I⋯O [2.994 (3) Å] halogen bonding links the mol-ecules into centrosymmetric dimers, which are further packed into ribbons along the c axis by inter-molecular sulfin-yl-sulfinyl inter-actions [S⋯O 3.128 (3) Å].

Related literature

For the crystal structures of similar isopropyl 2-(3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives, see Choi et al. (2008a ▶,b ▶). For a review of halogen bonding, see Politzer et al. (2007 ▶). For a review of carbon­yl–carbonyl inter­actions, see Allen et al. (1998 ▶).

Experimental

Crystal data

C15H17IO4S

M = 420.25

Monoclinic,

a = 17.615 (2) Å

b = 10.0905 (7) Å

c = 19.144 (1) Å

β = 99.177 (2)°

V = 3359.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 2.04 mm−1

T = 298 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.480, T max = 0.667

6667 measured reflections

2897 independent reflections

2172 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.064

S = 1.24

2897 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.37 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/S1600536808038671/cv2478sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038671/cv2478Isup2.hkl

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

C15H17IO4S	F000 = 1664
Mr = 420.25	Dx = 1.662 Mg m−3
Monoclinic, C2/c	Melting point = 420–421 K
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 17.615 (2) Å	Cell parameters from 5394 reflections
b = 10.0905 (7) Å	θ = 2.2–28.1º
c = 19.144 (1) Å	µ = 2.04 mm−1
β = 99.177 (2)º	T = 298 (2) K
V = 3359.2 (5) Å3	Block, colourless
Z = 8	0.40 × 0.30 × 0.20 mm

Bruker SMART CCD diffractometer	2897 independent reflections
Radiation source: fine-focus sealed tube	2172 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 298(2) K	θmin = 2.5º
φ and ω scans	h = −12→21
Absorption correction: multi-scan(SADABS; Sheldrick, 1999)	k = −12→12
Tmin = 0.480, Tmax = 0.667	l = −23→23
6667 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.064	w = 1/[σ2(Fo2)]
S = 1.24	(Δ/σ)max < 0.001
2897 reflections	Δρmax = 0.49 e Å−3
192 parameters	Δρmin = −0.37 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	0.513353 (18)	0.743648 (18)	−0.024404 (13)	0.04774 (10)
S	0.60070 (6)	0.34161 (6)	0.23510 (5)	0.0450 (2)
O1	0.61238 (16)	0.71392 (18)	0.29955 (13)	0.0445 (7)
O2	0.71791 (17)	0.4874 (2)	0.48324 (13)	0.0503 (7)
O3	0.7643 (2)	0.5249 (3)	0.38247 (15)	0.0783 (10)
O4	0.53494 (17)	0.3086 (2)	0.17899 (13)	0.0554 (7)
C1	0.6014 (2)	0.5163 (3)	0.24557 (19)	0.0408 (9)
C2	0.5868 (2)	0.6160 (2)	0.19074 (19)	0.0382 (9)
C3	0.5656 (2)	0.6170 (3)	0.11784 (18)	0.0389 (9)
H3	0.5604	0.5386	0.0920	0.047*
C4	0.5524 (2)	0.7395 (2)	0.0848 (2)	0.0394 (8)
C5	0.5640 (2)	0.8584 (3)	0.12417 (19)	0.0430 (9)
H5	0.5567	0.9388	0.1003	0.052*
C6	0.5853 (2)	0.8597 (3)	0.19600 (19)	0.0414 (9)
C7	0.5950 (2)	0.7356 (2)	0.2277 (2)	0.0385 (8)
C8	0.6142 (2)	0.5781 (3)	0.30852 (19)	0.0409 (9)
C9	0.6276 (2)	0.5310 (3)	0.3828 (2)	0.0470 (10)
H9A	0.6021	0.4463	0.3851	0.056*
H9B	0.6042	0.5932	0.4116	0.056*
C10	0.7106 (3)	0.5155 (3)	0.4138 (2)	0.0452 (10)
C11	0.7939 (3)	0.4653 (4)	0.5226 (2)	0.0575 (11)
H11	0.8262	0.4217	0.4922	0.069*
C12	0.7830 (3)	0.3742 (4)	0.5829 (2)	0.0690 (13)
H12A	0.7593	0.2933	0.5642	0.083*
H12B	0.7507	0.4166	0.6121	0.083*
H12C	0.8321	0.3548	0.6106	0.083*
C13	0.8288 (3)	0.5958 (5)	0.5478 (3)	0.0918 (17)
H13A	0.7971	0.6382	0.5775	0.110*
H13B	0.8325	0.6513	0.5077	0.110*
H13C	0.8792	0.5813	0.5741	0.110*
C14	0.5999 (3)	0.9856 (3)	0.2391 (2)	0.0615 (12)
H14A	0.5901	0.9698	0.2863	0.092*
H14B	0.5664	1.0544	0.2176	0.092*
H14C	0.6525	1.0125	0.2407	0.092*
C15	0.6855 (3)	0.3293 (4)	0.1950 (3)	0.0887 (19)
H15A	0.6947	0.2381	0.1848	0.133*
H15B	0.7286	0.3636	0.2269	0.133*
H15C	0.6787	0.3796	0.1519	0.133*

	U11	U22	U33	U12	U13	U23
I	0.0565 (2)	0.04572 (12)	0.04033 (15)	−0.00107 (11)	0.00570 (13)	−0.00037 (10)
S	0.0481 (7)	0.0287 (3)	0.0571 (6)	−0.0014 (4)	0.0050 (5)	0.0060 (3)
O1	0.056 (2)	0.0353 (10)	0.0405 (15)	−0.0035 (10)	0.0028 (14)	0.0011 (9)
O2	0.0467 (19)	0.0623 (14)	0.0407 (16)	0.0041 (13)	0.0029 (14)	0.0026 (12)
O3	0.050 (2)	0.133 (2)	0.054 (2)	0.0157 (18)	0.0137 (18)	0.0208 (17)
O4	0.073 (2)	0.0443 (11)	0.0475 (17)	−0.0087 (12)	0.0045 (16)	−0.0040 (11)
C1	0.042 (2)	0.0309 (13)	0.048 (2)	−0.0029 (14)	0.0013 (18)	0.0044 (13)
C2	0.036 (2)	0.0290 (13)	0.049 (2)	−0.0007 (13)	0.0047 (19)	0.0011 (13)
C3	0.041 (2)	0.0303 (13)	0.044 (2)	−0.0048 (13)	0.0030 (19)	−0.0053 (13)
C4	0.038 (2)	0.0395 (15)	0.040 (2)	−0.0008 (14)	0.0057 (18)	0.0016 (13)
C5	0.049 (3)	0.0282 (13)	0.051 (2)	−0.0017 (14)	0.007 (2)	0.0047 (14)
C6	0.049 (3)	0.0318 (14)	0.042 (2)	−0.0027 (14)	0.0035 (19)	−0.0004 (13)
C7	0.040 (2)	0.0319 (14)	0.041 (2)	−0.0033 (13)	0.0007 (18)	−0.0019 (13)
C8	0.038 (2)	0.0351 (14)	0.048 (2)	−0.0014 (14)	0.0022 (19)	0.0053 (14)
C9	0.046 (3)	0.0473 (16)	0.047 (2)	−0.0063 (17)	0.004 (2)	0.0062 (15)
C10	0.047 (3)	0.0417 (15)	0.047 (2)	0.0019 (16)	0.008 (2)	0.0035 (15)
C11	0.047 (3)	0.078 (2)	0.045 (3)	0.019 (2)	−0.002 (2)	0.0008 (19)
C12	0.084 (4)	0.068 (2)	0.051 (3)	0.014 (2)	−0.002 (3)	0.0033 (19)
C13	0.077 (4)	0.117 (4)	0.076 (4)	−0.037 (3)	−0.004 (3)	0.007 (3)
C14	0.086 (4)	0.0306 (14)	0.064 (3)	−0.0021 (17)	−0.002 (2)	−0.0057 (15)
C15	0.073 (4)	0.052 (2)	0.151 (6)	0.006 (2)	0.049 (4)	−0.001 (2)

I—C4	2.095 (4)	C6—C14	1.514 (4)
I—O4i	2.994 (3)	C8—C9	1.483 (5)
S—O4	1.486 (3)	C9—C10	1.496 (5)
S—O4ii	3.128 (3)	C9—H9A	0.9700
S—C1	1.773 (3)	C9—H9B	0.9700
S—C15	1.789 (4)	C11—C13	1.500 (6)
O1—C7	1.378 (4)	C11—C12	1.511 (5)
O1—C8	1.381 (3)	C11—H11	0.9800
O2—C10	1.346 (4)	C12—H12A	0.9600
O2—C11	1.445 (6)	C12—H12B	0.9600
O3—C10	1.201 (4)	C12—H12C	0.9600
C1—C8	1.344 (5)	C13—H13A	0.9600
C1—C2	1.447 (5)	C13—H13B	0.9600
C2—C3	1.386 (5)	C13—H13C	0.9600
C2—C7	1.395 (4)	C14—H14A	0.9600
C3—C4	1.392 (4)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.414 (4)	C15—H15A	0.9600
C5—C6	1.367 (5)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.390 (4)
I···O4i	2.994 (3)	S···O4ii	3.128 (3)
O4—S—C1	107.19 (17)	H9A—C9—H9B	107.6
C4—I—O4i	168.51 (9)	O3—C10—O2	123.5 (4)
O4—S—C15	106.4 (2)	O3—C10—C9	126.3 (4)
C1—S—C15	97.22 (16)	O2—C10—C9	110.3 (3)
C7—O1—C8	106.2 (2)	O2—C11—C13	109.3 (3)
C10—O2—C11	118.8 (3)	O2—C11—C12	105.8 (4)
C8—C1—C2	108.2 (3)	C13—C11—C12	112.6 (4)
C8—C1—S	124.1 (3)	O2—C11—H11	109.7
C2—C1—S	127.7 (3)	C13—C11—H11	109.7
C3—C2—C7	119.6 (3)	C12—C11—H11	109.7
C3—C2—C1	136.4 (3)	C11—C12—H12A	109.5
C7—C2—C1	104.0 (3)	C11—C12—H12B	109.5
C2—C3—C4	117.6 (3)	H12A—C12—H12B	109.5
C2—C3—H3	121.2	C11—C12—H12C	109.5
C4—C3—H3	121.2	H12A—C12—H12C	109.5
C3—C4—C5	120.8 (4)	H12B—C12—H12C	109.5
C3—C4—I	118.4 (2)	C11—C13—H13A	109.5
C5—C4—I	120.7 (2)	C11—C13—H13B	109.5
C6—C5—C4	122.5 (3)	H13A—C13—H13B	109.5
C6—C5—H5	118.7	C11—C13—H13C	109.5
C4—C5—H5	118.7	H13A—C13—H13C	109.5
C5—C6—C7	115.2 (3)	H13B—C13—H13C	109.5
C5—C6—C14	123.5 (3)	C6—C14—H14A	109.5
C7—C6—C14	121.3 (3)	C6—C14—H14B	109.5
O1—C7—C6	124.8 (3)	H14A—C14—H14B	109.5
O1—C7—C2	110.9 (2)	C6—C14—H14C	109.5
C6—C7—C2	124.2 (4)	H14A—C14—H14C	109.5
C1—C8—O1	110.6 (3)	H14B—C14—H14C	109.5
C1—C8—C9	133.6 (3)	S—C15—H15A	109.5
O1—C8—C9	115.8 (3)	S—C15—H15B	109.5
C8—C9—C10	114.2 (3)	H15A—C15—H15B	109.5
C8—C9—H9A	108.7	S—C15—H15C	109.5
C10—C9—H9A	108.7	H15A—C15—H15C	109.5
C8—C9—H9B	108.7	H15B—C15—H15C	109.5
C10—C9—H9B	108.7
O4—S—C1—C8	137.8 (3)	C5—C6—C7—C2	2.3 (6)
C15—S—C1—C8	−112.5 (4)	C14—C6—C7—C2	−176.2 (4)
O4—S—C1—C2	−40.3 (4)	C3—C2—C7—O1	176.9 (3)
C15—S—C1—C2	69.4 (4)	C1—C2—C7—O1	−0.6 (4)
C8—C1—C2—C3	−175.0 (4)	C3—C2—C7—C6	−1.9 (6)
S—C1—C2—C3	3.4 (7)	C1—C2—C7—C6	−179.4 (4)
C8—C1—C2—C7	1.9 (4)	C2—C1—C8—O1	−2.5 (4)
S—C1—C2—C7	−179.8 (3)	S—C1—C8—O1	179.1 (3)
C7—C2—C3—C4	−0.8 (5)	C2—C1—C8—C9	175.8 (4)
C1—C2—C3—C4	175.7 (4)	S—C1—C8—C9	−2.6 (6)
C2—C3—C4—C5	3.0 (5)	C7—O1—C8—C1	2.1 (4)
C2—C3—C4—I	−176.1 (2)	C7—O1—C8—C9	−176.6 (3)
C3—C4—C5—C6	−2.7 (6)	C1—C8—C9—C10	93.3 (5)
I—C4—C5—C6	176.4 (3)	O1—C8—C9—C10	−88.4 (4)
C4—C5—C6—C7	0.1 (5)	C11—O2—C10—O3	−0.9 (5)
C4—C5—C6—C14	178.5 (4)	C11—O2—C10—C9	178.4 (3)
C8—O1—C7—C6	178.0 (4)	C8—C9—C10—O3	−7.7 (5)
C8—O1—C7—C2	−0.8 (4)	C8—C9—C10—O2	172.9 (2)
C5—C6—C7—O1	−176.4 (3)	C10—O2—C11—C13	86.0 (4)
C14—C6—C7—O1	5.1 (6)	C10—O2—C11—C12	−152.5 (3)

Table 1

Selected interatomic distances (Å)

I⋯O4i	2.994 (3)
S⋯O4ii	3.128 (3)

Symmetry codes: (i) ; (ii) .