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

In the title mol-ecule, C(16)H(19)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, pairs of mol-ecules are linked by I⋯O [3.114 (3) Å] halogen bonding into centrosymmetric dimers. The crystal structure is further stabilized by weak inter-molecular C-H⋯O nonclassical hydrogen bonds.

Related literature

For the crystal structures of similar alkyl 2-(5-iodo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives, see Choi et al. (2009a ▶,b ▶). For a review of halogen bonding, see Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H19IO4S

M = 434.27

Monoclinic,

a = 10.6726 (9) Å

b = 15.423 (1) Å

c = 10.7343 (9) Å

β = 102.334 (2)°

V = 1726.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.99 mm−1

T = 173 K

0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.503, T max = 0.587 (expected range = 0.472–0.550)

9111 measured reflections

3357 independent reflections

3152 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.079

S = 1.23

3357 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.71 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/S1600536809011210/cv2534sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011210/cv2534Isup2.hkl

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

C16H19IO4S	F(000) = 864
Mr = 434.27	Dx = 1.671 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7114 reflections
a = 10.6726 (9) Å	θ = 2.4–28.3°
b = 15.423 (1) Å	µ = 1.99 mm−1
c = 10.7343 (9) Å	T = 173 K
β = 102.334 (2)°	Block, colourless
V = 1726.1 (2) Å3	0.40 × 0.40 × 0.30 mm
Z = 4

Bruker SMART CCD diffractometer	3357 independent reflections
Radiation source: fine-focus sealed tube	3152 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 26.0°, θmin = 2.4°
φ and ω scans	h = −13→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→19
Tmin = 0.503, Tmax = 0.587	l = −12→13
9111 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: difference Fourier map
wR(F2) = 0.079	H-atom parameters constrained
S = 1.23	w = 1/[σ2(Fo2) + (0.0195P)2 + 3.2932P] where P = (Fo2 + 2Fc2)/3
3357 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.71 e Å−3

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	0.98665 (2)	0.636473 (16)	0.87775 (2)	0.03496 (10)
S	0.60639 (9)	0.32117 (6)	0.94130 (8)	0.0275 (2)
O1	0.4562 (2)	0.47524 (17)	0.6559 (2)	0.0306 (6)
O2	0.1263 (2)	0.34631 (17)	0.6994 (2)	0.0323 (6)
O3	0.2500 (3)	0.43238 (19)	0.8438 (3)	0.0422 (7)
O4	0.7470 (2)	0.30422 (17)	0.9660 (3)	0.0360 (6)
C1	0.5707 (3)	0.4021 (2)	0.8231 (3)	0.0248 (7)
C2	0.6445 (3)	0.4775 (2)	0.8026 (3)	0.0241 (7)
C3	0.7649 (3)	0.5115 (2)	0.8584 (3)	0.0244 (7)
H3	0.8189	0.4845	0.9296	0.029*
C4	0.8018 (3)	0.5868 (2)	0.8045 (3)	0.0281 (7)
C5	0.7231 (4)	0.6290 (2)	0.7033 (4)	0.0311 (8)
H5	0.7515	0.6812	0.6713	0.037*
C6	0.6029 (4)	0.5957 (2)	0.6480 (3)	0.0323 (8)
H6	0.5475	0.6239	0.5788	0.039*
C7	0.5685 (3)	0.5196 (2)	0.6990 (3)	0.0275 (8)
C8	0.4610 (3)	0.4037 (2)	0.7323 (3)	0.0290 (8)
C9	0.3470 (3)	0.3461 (3)	0.7034 (4)	0.0329 (9)
H9A	0.3707	0.2879	0.7398	0.040*
H9B	0.3185	0.3399	0.6099	0.040*
C10	0.2375 (3)	0.3817 (2)	0.7578 (3)	0.0285 (8)
C11	0.0149 (4)	0.3741 (3)	0.7474 (4)	0.0439 (10)
H11A	0.0056	0.4379	0.7412	0.053*
H11B	0.0246	0.3571	0.8379	0.053*
C12	−0.1006 (4)	0.3307 (3)	0.6670 (4)	0.0366 (9)
H12A	−0.1757	0.3436	0.7042	0.044*
H12B	−0.0868	0.2672	0.6724	0.044*
C13	−0.1330 (4)	0.3561 (3)	0.5274 (4)	0.0409 (10)
H13	−0.0564	0.3437	0.4905	0.049*
C14	−0.2427 (5)	0.2997 (4)	0.4585 (6)	0.080 (2)
H14A	−0.2175	0.2385	0.4684	0.120*
H14B	−0.2631	0.3147	0.3677	0.120*
H14C	−0.3183	0.3093	0.4949	0.120*
C15	−0.1639 (5)	0.4518 (4)	0.5093 (5)	0.0607 (14)
H15A	−0.2415	0.4649	0.5408	0.091*
H15B	−0.1781	0.4664	0.4185	0.091*
H15C	−0.0921	0.4861	0.5570	0.091*
C16	0.5774 (4)	0.3837 (3)	1.0723 (4)	0.0367 (9)
H16A	0.5952	0.3483	1.1499	0.055*
H16B	0.4876	0.4025	1.0546	0.055*
H16C	0.6335	0.4347	1.0844	0.055*

	U11	U22	U33	U12	U13	U23
I	0.03406 (15)	0.03270 (15)	0.03724 (15)	−0.01078 (10)	0.00567 (10)	0.00262 (11)
S	0.0287 (5)	0.0217 (4)	0.0313 (4)	−0.0019 (3)	0.0046 (4)	−0.0022 (3)
O1	0.0250 (13)	0.0389 (14)	0.0249 (12)	0.0014 (11)	−0.0010 (10)	−0.0019 (11)
O2	0.0220 (12)	0.0414 (15)	0.0322 (13)	0.0005 (11)	0.0032 (10)	−0.0092 (11)
O3	0.0378 (16)	0.0473 (17)	0.0421 (16)	−0.0048 (13)	0.0102 (13)	−0.0208 (14)
O4	0.0285 (14)	0.0327 (14)	0.0448 (16)	0.0031 (11)	0.0030 (12)	0.0004 (12)
C1	0.0253 (17)	0.0234 (17)	0.0256 (17)	0.0004 (14)	0.0052 (14)	−0.0033 (14)
C2	0.0240 (17)	0.0256 (17)	0.0232 (16)	0.0027 (14)	0.0062 (13)	−0.0033 (13)
C3	0.0236 (17)	0.0273 (17)	0.0215 (16)	0.0013 (14)	0.0034 (13)	0.0009 (13)
C4	0.0275 (18)	0.0285 (18)	0.0283 (18)	0.0008 (15)	0.0059 (14)	−0.0023 (15)
C5	0.038 (2)	0.0248 (18)	0.0326 (19)	0.0008 (15)	0.0128 (16)	0.0011 (15)
C6	0.040 (2)	0.0325 (19)	0.0228 (17)	0.0080 (17)	0.0028 (15)	0.0014 (15)
C7	0.0287 (19)	0.0304 (18)	0.0229 (16)	0.0034 (15)	0.0046 (14)	−0.0019 (14)
C8	0.0261 (18)	0.0315 (19)	0.0292 (18)	0.0029 (15)	0.0051 (14)	−0.0072 (15)
C9	0.0237 (18)	0.035 (2)	0.039 (2)	−0.0035 (15)	0.0030 (16)	−0.0122 (16)
C10	0.0270 (18)	0.0294 (18)	0.0273 (17)	0.0008 (15)	0.0019 (14)	0.0000 (15)
C11	0.030 (2)	0.064 (3)	0.039 (2)	0.008 (2)	0.0081 (17)	−0.009 (2)
C12	0.0242 (19)	0.042 (2)	0.045 (2)	0.0004 (17)	0.0108 (17)	−0.0001 (18)
C13	0.035 (2)	0.046 (2)	0.040 (2)	0.0111 (19)	0.0043 (18)	−0.0060 (19)
C14	0.048 (3)	0.091 (5)	0.089 (4)	0.002 (3)	−0.014 (3)	−0.037 (4)
C15	0.059 (3)	0.065 (3)	0.058 (3)	0.025 (3)	0.014 (3)	0.015 (3)
C16	0.049 (2)	0.034 (2)	0.0293 (19)	0.0004 (18)	0.0129 (17)	−0.0031 (16)

I—C4	2.106 (4)	C9—C10	1.515 (5)
I—O4i	3.114 (3)	C9—H9A	0.9900
S—O4	1.490 (3)	C9—H9B	0.9900
S—C1	1.762 (4)	C11—C12	1.503 (6)
S—C16	1.786 (4)	C11—H11A	0.9900
O1—C8	1.369 (5)	C11—H11B	0.9900
O1—C7	1.372 (4)	C12—C13	1.516 (6)
O2—C10	1.335 (4)	C12—H12A	0.9900
O2—C11	1.457 (5)	C12—H12B	0.9900
O3—C10	1.195 (4)	C13—C15	1.517 (6)
C1—C8	1.355 (5)	C13—C14	1.518 (7)
C1—C2	1.448 (5)	C13—H13	1.0000
C2—C7	1.390 (5)	C14—H14A	0.9800
C2—C3	1.398 (5)	C14—H14B	0.9800
C3—C4	1.391 (5)	C14—H14C	0.9800
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.386 (5)	C15—H15B	0.9800
C5—C6	1.392 (5)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.379 (5)	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
C8—C9	1.484 (5)
C4—I—O4i	169.4 (1)	O2—C10—C9	110.6 (3)
O4—S—C1	107.9 (2)	O2—C11—C12	107.3 (3)
O4—S—C16	107.0 (2)	O2—C11—H11A	110.3
C1—S—C16	97.9 (2)	C12—C11—H11A	110.3
C8—O1—C7	106.4 (3)	O2—C11—H11B	110.3
C10—O2—C11	115.1 (3)	C12—C11—H11B	110.3
C8—C1—C2	106.9 (3)	H11A—C11—H11B	108.5
C8—C1—S	123.5 (3)	C11—C12—C13	116.0 (4)
C2—C1—S	129.6 (3)	C11—C12—H12A	108.3
C7—C2—C3	119.6 (3)	C13—C12—H12A	108.3
C7—C2—C1	104.6 (3)	C11—C12—H12B	108.3
C3—C2—C1	135.8 (3)	C13—C12—H12B	108.3
C4—C3—C2	116.8 (3)	H12A—C12—H12B	107.4
C4—C3—H3	121.6	C12—C13—C15	112.1 (4)
C2—C3—H3	121.6	C12—C13—C14	108.8 (4)
C5—C4—C3	122.7 (3)	C15—C13—C14	111.8 (4)
C5—C4—I	119.0 (3)	C12—C13—H13	108.0
C3—C4—I	118.3 (3)	C15—C13—H13	108.0
C4—C5—C6	120.7 (3)	C14—C13—H13	108.0
C4—C5—H5	119.6	C13—C14—H14A	109.5
C6—C5—H5	119.6	C13—C14—H14B	109.5
C7—C6—C5	116.3 (3)	H14A—C14—H14B	109.5
C7—C6—H6	121.8	C13—C14—H14C	109.5
C5—C6—H6	121.8	H14A—C14—H14C	109.5
O1—C7—C6	125.3 (3)	H14B—C14—H14C	109.5
O1—C7—C2	110.9 (3)	C13—C15—H15A	109.5
C6—C7—C2	123.8 (3)	C13—C15—H15B	109.5
C1—C8—O1	111.2 (3)	H15A—C15—H15B	109.5
C1—C8—C9	133.1 (4)	C13—C15—H15C	109.5
O1—C8—C9	115.7 (3)	H15A—C15—H15C	109.5
C8—C9—C10	111.6 (3)	H15B—C15—H15C	109.5
C8—C9—H9A	109.3	S—C16—H16A	109.5
C10—C9—H9A	109.3	S—C16—H16B	109.5
C8—C9—H9B	109.3	H16A—C16—H16B	109.5
C10—C9—H9B	109.3	S—C16—H16C	109.5
H9A—C9—H9B	108.0	H16A—C16—H16C	109.5
O3—C10—O2	124.8 (4)	H16B—C16—H16C	109.5
O3—C10—C9	124.5 (3)
O4—S—C1—C8	144.4 (3)	C3—C2—C7—O1	178.4 (3)
C16—S—C1—C8	−104.9 (3)	C1—C2—C7—O1	−0.3 (4)
O4—S—C1—C2	−36.8 (4)	C3—C2—C7—C6	−1.8 (5)
C16—S—C1—C2	74.0 (4)	C1—C2—C7—C6	179.5 (3)
C8—C1—C2—C7	1.0 (4)	C2—C1—C8—O1	−1.3 (4)
S—C1—C2—C7	−178.0 (3)	S—C1—C8—O1	177.8 (2)
C8—C1—C2—C3	−177.4 (4)	C2—C1—C8—C9	−179.0 (4)
S—C1—C2—C3	3.6 (6)	S—C1—C8—C9	0.0 (6)
C7—C2—C3—C4	−0.4 (5)	C7—O1—C8—C1	1.1 (4)
C1—C2—C3—C4	177.7 (4)	C7—O1—C8—C9	179.3 (3)
C2—C3—C4—C5	2.2 (5)	C1—C8—C9—C10	98.3 (5)
C2—C3—C4—I	−176.4 (2)	O1—C8—C9—C10	−79.4 (4)
O4i—I—C4—C5	149.4 (5)	C11—O2—C10—O3	0.4 (5)
O4i—I—C4—C3	−31.9 (8)	C11—O2—C10—C9	178.1 (3)
C3—C4—C5—C6	−1.9 (6)	C8—C9—C10—O3	−21.8 (6)
I—C4—C5—C6	176.7 (3)	C8—C9—C10—O2	160.4 (3)
C4—C5—C6—C7	−0.3 (5)	C10—O2—C11—C12	177.6 (3)
C8—O1—C7—C6	179.7 (3)	O2—C11—C12—C13	−64.3 (5)
C8—O1—C7—C2	−0.4 (4)	C11—C12—C13—C15	−61.6 (5)
C5—C6—C7—O1	−178.1 (3)	C11—C12—C13—C14	174.2 (4)
C5—C6—C7—C2	2.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ii	0.95	2.41	3.310 (5)	159
C16—H16C···O3iii	0.98	2.44	3.397 (5)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.95	2.41	3.310 (5)	159
C16—H16C⋯O3ii	0.98	2.44	3.397 (5)	167

Symmetry codes: (i) ; (ii) .