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

In the title compound, C(14)H(15)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. The crystal structure is stabilized by C-H⋯π inter-actions between a methyl H atom and the benzene ring of an adjacent mol-ecule, and by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar isopropyl 2-(3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C14H15IO4S

M = 406.22

Triclinic,

a = 8.0584 (7) Å

b = 10.1959 (9) Å

c = 10.8367 (9) Å

α = 70.369 (2)°

β = 81.926 (2)°

γ = 66.882 (1)°

V = 771.24 (12) Å3

Z = 2

Mo Kα radiation

μ = 2.22 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.595, T max = 0.806

4396 measured reflections

2965 independent reflections

2639 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.13

2965 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.57 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/S1600536808037471/bq2107sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037471/bq2107Isup2.hkl

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

C14H15IO4S	Z = 2
Mr = 406.22	F000 = 400
Triclinic, P1	Dx = 1.749 Mg m−3
Hall symbol: -P 1	Melting point = 420–421 K
a = 8.0584 (7) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.1959 (9) Å	Cell parameters from 3094 reflections
c = 10.8367 (9) Å	θ = 2.5–28.2º
α = 70.369 (2)º	µ = 2.22 mm−1
β = 81.926 (2)º	T = 298 (2) K
γ = 66.882 (1)º	Block, colorless
V = 771.24 (12) Å3	0.30 × 0.20 × 0.10 mm

Bruker SMART CCD diffractometer	2965 independent reflections
Radiation source: fine-focus sealed tube	2639 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.011
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 298(2) K	θmin = 2.5º
φ and ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Sheldrick, 1999)	k = −12→10
Tmin = 0.595, Tmax = 0.806	l = −11→13
4396 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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.6769P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
2965 reflections	Δρmax = 0.62 e Å−3
182 parameters	Δρmin = −0.57 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	0.70596 (3)	0.79850 (3)	0.12855 (3)	0.05948 (12)
S	0.25632 (12)	0.39419 (10)	0.46216 (8)	0.0450 (2)
O1	0.1637 (3)	0.5266 (2)	0.0838 (2)	0.0396 (5)
O2	−0.0175 (4)	0.1492 (3)	0.2759 (3)	0.0541 (6)
O3	0.2647 (4)	0.1371 (3)	0.2867 (3)	0.0668 (8)
O4	0.2538 (4)	0.5137 (3)	0.5137 (3)	0.0601 (7)
C1	0.2512 (4)	0.4675 (3)	0.2898 (3)	0.0362 (6)
C2	0.3469 (4)	0.5580 (3)	0.2042 (3)	0.0349 (6)
C3	0.4715 (4)	0.6148 (4)	0.2202 (3)	0.0398 (7)
H3	0.5164	0.5932	0.3022	0.048*
C4	0.5252 (4)	0.7044 (3)	0.1086 (3)	0.0406 (7)
C5	0.4622 (5)	0.7382 (4)	−0.0162 (3)	0.0430 (7)
H5	0.5030	0.7988	−0.0884	0.052*
C6	0.3394 (5)	0.6817 (4)	−0.0328 (3)	0.0413 (7)
H6	0.2955	0.7026	−0.1149	0.050*
C7	0.2851 (4)	0.5925 (3)	0.0795 (3)	0.0369 (7)
C8	0.1443 (4)	0.4531 (3)	0.2138 (3)	0.0377 (7)
C9	0.0157 (5)	0.3741 (4)	0.2441 (4)	0.0434 (7)
H9A	−0.0662	0.4154	0.1712	0.052*
H9B	−0.0556	0.3928	0.3207	0.052*
C10	0.1072 (5)	0.2070 (4)	0.2695 (3)	0.0414 (7)
C11	0.0424 (6)	−0.0125 (4)	0.2990 (4)	0.0661 (12)
H11	0.1531	−0.0670	0.3506	0.079*
C12	−0.1125 (10)	−0.0567 (7)	0.3724 (6)	0.104 (2)
H12A	−0.2185	−0.0037	0.3191	0.125*
H12B	−0.1363	−0.0315	0.4526	0.125*
H12C	−0.0805	−0.1626	0.3919	0.125*
C13	0.0701 (9)	−0.0397 (5)	0.1698 (6)	0.0926 (18)
H13A	0.1579	−0.0006	0.1195	0.111*
H13B	−0.0420	0.0096	0.1235	0.111*
H13C	0.1124	−0.1454	0.1828	0.111*
C14	0.4840 (6)	0.2608 (5)	0.4771 (4)	0.0647 (11)
H14A	0.5657	0.3127	0.4443	0.097*
H14B	0.4989	0.1947	0.4273	0.097*
H14C	0.5092	0.2035	0.5675	0.097*

	U11	U22	U33	U12	U13	U23
I	0.05565 (17)	0.05111 (16)	0.0792 (2)	−0.03419 (12)	−0.00801 (12)	−0.00920 (12)
S	0.0496 (5)	0.0512 (5)	0.0385 (4)	−0.0270 (4)	−0.0031 (3)	−0.0082 (4)
O1	0.0425 (12)	0.0397 (12)	0.0418 (12)	−0.0179 (10)	−0.0069 (9)	−0.0131 (10)
O2	0.0601 (15)	0.0406 (13)	0.0698 (17)	−0.0273 (12)	−0.0179 (12)	−0.0099 (12)
O3	0.0509 (16)	0.0473 (15)	0.100 (2)	−0.0204 (13)	−0.0092 (15)	−0.0144 (15)
O4	0.0719 (18)	0.0681 (18)	0.0502 (15)	−0.0283 (15)	−0.0032 (13)	−0.0264 (13)
C1	0.0400 (16)	0.0352 (15)	0.0373 (17)	−0.0179 (13)	−0.0038 (13)	−0.0099 (13)
C2	0.0376 (15)	0.0296 (14)	0.0383 (17)	−0.0123 (12)	−0.0044 (12)	−0.0100 (12)
C3	0.0412 (17)	0.0383 (17)	0.0438 (18)	−0.0179 (14)	−0.0052 (13)	−0.0120 (14)
C4	0.0376 (16)	0.0324 (16)	0.055 (2)	−0.0157 (13)	−0.0010 (14)	−0.0135 (14)
C5	0.0472 (18)	0.0347 (16)	0.0434 (19)	−0.0159 (14)	0.0017 (14)	−0.0073 (14)
C6	0.0462 (18)	0.0385 (17)	0.0371 (17)	−0.0140 (14)	−0.0040 (13)	−0.0097 (13)
C7	0.0394 (16)	0.0315 (15)	0.0435 (18)	−0.0137 (13)	−0.0045 (13)	−0.0138 (13)
C8	0.0419 (16)	0.0336 (15)	0.0414 (17)	−0.0155 (13)	−0.0040 (13)	−0.0128 (13)
C9	0.0439 (18)	0.0441 (18)	0.0512 (19)	−0.0228 (15)	−0.0039 (14)	−0.0165 (15)
C10	0.050 (2)	0.0435 (18)	0.0382 (17)	−0.0264 (16)	−0.0039 (14)	−0.0100 (14)
C11	0.085 (3)	0.0381 (19)	0.078 (3)	−0.031 (2)	−0.034 (2)	0.0010 (19)
C12	0.178 (7)	0.097 (4)	0.080 (4)	−0.099 (5)	0.029 (4)	−0.032 (3)
C13	0.116 (4)	0.052 (3)	0.104 (4)	−0.032 (3)	0.044 (3)	−0.034 (3)
C14	0.061 (2)	0.059 (2)	0.060 (2)	−0.012 (2)	−0.0181 (19)	−0.006 (2)

I—C4	2.101 (3)	C6—C7	1.385 (5)
S—O4	1.494 (3)	C6—H6	0.9300
S—C1	1.763 (3)	C8—C9	1.488 (4)
S—C14	1.794 (4)	C9—C10	1.509 (5)
O1—C7	1.375 (4)	C9—H9A	0.9700
O1—C8	1.375 (4)	C9—H9B	0.9700
O2—C10	1.335 (4)	C11—C13	1.487 (7)
O2—C11	1.465 (4)	C11—C12	1.521 (7)
O3—C10	1.192 (4)	C11—H11	0.9800
C1—C8	1.350 (4)	C12—H12A	0.9600
C1—C2	1.445 (4)	C12—H12B	0.9600
C2—C7	1.390 (4)	C12—H12C	0.9600
C2—C3	1.395 (4)	C13—H13A	0.9600
C3—C4	1.380 (5)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.396 (5)	C14—H14A	0.9600
C5—C6	1.382 (5)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
O4—S—C1	107.22 (15)	C10—C9—H9A	108.9
O4—S—C14	106.49 (19)	C8—C9—H9B	108.9
C1—S—C14	97.67 (18)	C10—C9—H9B	108.9
C7—O1—C8	106.2 (2)	H9A—C9—H9B	107.7
C10—O2—C11	118.3 (3)	O3—C10—O2	125.4 (3)
C8—C1—C2	107.2 (3)	O3—C10—C9	125.4 (3)
C8—C1—S	124.0 (2)	O2—C10—C9	109.1 (3)
C2—C1—S	128.7 (2)	O2—C11—C13	108.2 (3)
C7—C2—C3	119.4 (3)	O2—C11—C12	105.4 (4)
C7—C2—C1	104.7 (3)	C13—C11—C12	109.8 (4)
C3—C2—C1	135.9 (3)	O2—C11—H11	111.1
C4—C3—C2	116.9 (3)	C13—C11—H11	111.1
C4—C3—H3	121.6	C12—C11—H11	111.1
C2—C3—H3	121.6	C11—C12—H12A	109.5
C3—C4—C5	123.2 (3)	C11—C12—H12B	109.5
C3—C4—I	118.3 (2)	H12A—C12—H12B	109.5
C5—C4—I	118.5 (2)	C11—C12—H12C	109.5
C6—C5—C4	120.2 (3)	H12A—C12—H12C	109.5
C6—C5—H5	119.9	H12B—C12—H12C	109.5
C4—C5—H5	119.9	C11—C13—H13A	109.5
C5—C6—C7	116.4 (3)	C11—C13—H13B	109.5
C5—C6—H6	121.8	H13A—C13—H13B	109.5
C7—C6—H6	121.8	C11—C13—H13C	109.5
O1—C7—C6	125.3 (3)	H13A—C13—H13C	109.5
O1—C7—C2	110.7 (3)	H13B—C13—H13C	109.5
C6—C7—C2	123.9 (3)	S—C14—H14A	109.5
C1—C8—O1	111.1 (3)	S—C14—H14B	109.5
C1—C8—C9	132.6 (3)	H14A—C14—H14B	109.5
O1—C8—C9	116.3 (3)	S—C14—H14C	109.5
C8—C9—C10	113.4 (3)	H14A—C14—H14C	109.5
C8—C9—H9A	108.9	H14B—C14—H14C	109.5
O4—S—C1—C8	−135.0 (3)	C3—C2—C7—O1	180.0 (3)
C14—S—C1—C8	115.0 (3)	C1—C2—C7—O1	−1.5 (3)
O4—S—C1—C2	41.4 (3)	C3—C2—C7—C6	−0.2 (5)
C14—S—C1—C2	−68.6 (3)	C1—C2—C7—C6	178.3 (3)
C8—C1—C2—C7	0.6 (3)	C2—C1—C8—O1	0.6 (4)
S—C1—C2—C7	−176.3 (2)	S—C1—C8—O1	177.6 (2)
C8—C1—C2—C3	178.7 (4)	C2—C1—C8—C9	179.9 (3)
S—C1—C2—C3	1.9 (6)	S—C1—C8—C9	−3.1 (5)
C7—C2—C3—C4	0.5 (4)	C7—O1—C8—C1	−1.5 (3)
C1—C2—C3—C4	−177.4 (3)	C7—O1—C8—C9	179.1 (3)
C2—C3—C4—C5	−0.6 (5)	C1—C8—C9—C10	−78.0 (5)
C2—C3—C4—I	177.9 (2)	O1—C8—C9—C10	101.3 (3)
C3—C4—C5—C6	0.3 (5)	C11—O2—C10—O3	−3.5 (5)
I—C4—C5—C6	−178.2 (2)	C11—O2—C10—C9	179.5 (3)
C4—C5—C6—C7	0.1 (5)	C8—C9—C10—O3	12.3 (5)
C8—O1—C7—C6	−177.9 (3)	C8—C9—C10—O2	−170.7 (3)
C8—O1—C7—C2	1.8 (3)	C10—O2—C11—C13	−92.6 (4)
C5—C6—C7—O1	179.7 (3)	C10—O2—C11—C12	150.0 (4)
C5—C6—C7—C2	−0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4i	0.93	2.57	3.451 (4)	159
C9—H9B···O4ii	0.97	2.41	3.373 (4)	170
C13—H13C···Cgiii	0.96	2.78	3.532 (5)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4i	0.93	2.57	3.451 (4)	159
C9—H9B⋯O4ii	0.97	2.41	3.373 (4)	170
C13—H13C⋯Cgiii	0.96	2.78	3.532 (5)	136

Symmetry codes: (i) ; (ii) ; (iii) .