Propyl 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 ring system. The crystal structure is stabilized by inter-molecular C-H⋯π inter-actions between an H atom of the propyl methyl-ene group closest to the carboxyl-ate O atom and the benzene ring of a neighbouring mol-ecule, and between an H atom of the outer propyl methyl-ene group and the furan ring of a neighbouring mol-ecule, respectively. Additionally, the crystal structure exhibits inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the synthesis and crystal structures of similar alkyl 2-(5-iodo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C14H15IO4S

M = 406.22

Triclinic,

a = 8.5468 (4) Å

b = 10.0329 (5) Å

c = 10.3239 (5) Å

α = 72.442 (1)°

β = 81.345 (1)°

γ = 65.088 (1)°

V = 765.21 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.24 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.583, T max = 0.787

6182 measured reflections

2982 independent reflections

2778 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.069

S = 1.18

2982 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.56 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/S1600536808042359/sj2566sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042359/sj2566Isup2.hkl

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

C14H15IO4S	Z = 2
Mr = 406.22	F(000) = 400
Triclinic, P1	Dx = 1.763 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5468 (4) Å	Cell parameters from 4625 reflections
b = 10.0329 (5) Å	θ = 2.3–28.3°
c = 10.3239 (5) Å	µ = 2.24 mm−1
α = 72.442 (1)°	T = 293 K
β = 81.345 (1)°	Plate, colorless
γ = 65.088 (1)°	0.30 × 0.20 × 0.10 mm
V = 765.21 (6) Å3

Bruker SMART CCD diffractometer	2982 independent reflections
Radiation source: fine-focus sealed tube	2778 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 10.0 pixels mm-1	θmax = 26.0°, θmin = 2.3°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→12
Tmin = 0.583, Tmax = 0.787	l = −12→12
6182 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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F2) = 0.069	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0293P)2 + 0.5734P] where P = (Fo2 + 2Fc2)/3
2982 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.56 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	0.69366 (3)	0.79269 (3)	0.61486 (2)	0.04832 (10)
S	0.26183 (10)	0.40380 (10)	0.96397 (8)	0.03932 (18)
O1	0.1660 (3)	0.5368 (2)	0.5730 (2)	0.0350 (4)
O2	0.0455 (3)	0.1416 (3)	0.7355 (3)	0.0530 (6)
O3	0.2911 (3)	0.1379 (3)	0.7896 (3)	0.0567 (7)
O4	0.2582 (3)	0.5257 (3)	1.0206 (2)	0.0529 (6)
C1	0.2539 (4)	0.4770 (3)	0.7857 (3)	0.0337 (6)
C2	0.3414 (4)	0.5677 (3)	0.6976 (3)	0.0303 (6)
C3	0.4622 (4)	0.6215 (3)	0.7127 (3)	0.0335 (6)
H3	0.5072	0.5992	0.7969	0.040*
C4	0.5121 (4)	0.7091 (3)	0.5973 (3)	0.0340 (6)
C5	0.4466 (4)	0.7459 (3)	0.4690 (3)	0.0387 (7)
H5	0.4825	0.8069	0.3943	0.046*
C6	0.3287 (4)	0.6913 (3)	0.4533 (3)	0.0368 (7)
H6	0.2844	0.7134	0.3689	0.044*
C7	0.2796 (4)	0.6029 (3)	0.5682 (3)	0.0322 (6)
C8	0.1529 (4)	0.4619 (3)	0.7075 (3)	0.0330 (6)
C9	0.0405 (4)	0.3755 (3)	0.7359 (3)	0.0367 (7)
H9A	−0.0360	0.4135	0.6606	0.044*
H9B	−0.0303	0.3929	0.8168	0.044*
C10	0.1438 (4)	0.2060 (4)	0.7564 (3)	0.0396 (7)
C11	0.1272 (5)	−0.0221 (4)	0.7496 (6)	0.0702 (13)
H11A	0.1879	−0.0747	0.8343	0.084*
H11B	0.2094	−0.0435	0.6752	0.084*
C12	−0.0126 (6)	−0.0740 (5)	0.7479 (5)	0.0683 (12)
H12A	−0.0746	−0.0170	0.6641	0.082*
H12B	0.0396	−0.1808	0.7486	0.082*
C13	−0.1370 (9)	−0.0548 (7)	0.8641 (6)	0.102 (2)
H13A	−0.0787	−0.1189	0.9471	0.154*
H13B	−0.2278	−0.0829	0.8536	0.154*
H13C	−0.1850	0.0497	0.8670	0.154*
C14	0.4798 (5)	0.2651 (4)	0.9739 (4)	0.0539 (9)
H14A	0.5572	0.3159	0.9444	0.081*
H14B	0.4958	0.2005	0.9166	0.081*
H14C	0.5031	0.2045	1.0661	0.081*

	U11	U22	U33	U12	U13	U23
I	0.04655 (14)	0.04768 (14)	0.05934 (16)	−0.02881 (11)	−0.00540 (10)	−0.00948 (10)
S	0.0427 (4)	0.0487 (4)	0.0301 (4)	−0.0235 (4)	−0.0015 (3)	−0.0075 (3)
O1	0.0358 (11)	0.0404 (11)	0.0329 (11)	−0.0184 (9)	−0.0071 (8)	−0.0077 (9)
O2	0.0399 (12)	0.0362 (12)	0.0874 (19)	−0.0165 (10)	−0.0083 (12)	−0.0177 (12)
O3	0.0393 (13)	0.0466 (14)	0.0806 (19)	−0.0156 (11)	−0.0146 (12)	−0.0079 (13)
O4	0.0619 (16)	0.0638 (16)	0.0409 (13)	−0.0264 (13)	−0.0003 (11)	−0.0234 (12)
C1	0.0349 (15)	0.0350 (15)	0.0336 (15)	−0.0152 (13)	−0.0026 (12)	−0.0098 (12)
C2	0.0314 (14)	0.0304 (14)	0.0297 (14)	−0.0112 (12)	−0.0026 (11)	−0.0099 (11)
C3	0.0360 (15)	0.0335 (15)	0.0339 (16)	−0.0142 (12)	−0.0052 (12)	−0.0104 (12)
C4	0.0316 (15)	0.0311 (14)	0.0419 (16)	−0.0131 (12)	−0.0016 (12)	−0.0119 (13)
C5	0.0400 (17)	0.0335 (15)	0.0377 (16)	−0.0138 (13)	0.0009 (13)	−0.0049 (13)
C6	0.0392 (16)	0.0395 (16)	0.0301 (15)	−0.0150 (13)	−0.0048 (12)	−0.0062 (13)
C7	0.0299 (14)	0.0311 (14)	0.0378 (15)	−0.0111 (12)	−0.0053 (12)	−0.0118 (12)
C8	0.0339 (15)	0.0320 (15)	0.0335 (15)	−0.0142 (12)	−0.0027 (12)	−0.0070 (12)
C9	0.0343 (15)	0.0412 (16)	0.0410 (17)	−0.0188 (13)	−0.0023 (13)	−0.0134 (13)
C10	0.0397 (17)	0.0422 (17)	0.0403 (17)	−0.0220 (14)	0.0007 (13)	−0.0082 (14)
C11	0.051 (2)	0.038 (2)	0.122 (4)	−0.0153 (17)	−0.001 (2)	−0.027 (2)
C12	0.063 (3)	0.043 (2)	0.105 (4)	−0.0231 (19)	−0.004 (2)	−0.026 (2)
C13	0.124 (5)	0.100 (4)	0.111 (5)	−0.078 (4)	0.044 (4)	−0.040 (4)
C14	0.051 (2)	0.055 (2)	0.049 (2)	−0.0147 (17)	−0.0128 (16)	−0.0084 (17)

I—C4	2.102 (3)	C6—C7	1.379 (4)
S—O4	1.494 (3)	C6—H6	0.9300
S—C1	1.764 (3)	C8—C9	1.491 (4)
S—C14	1.790 (4)	C9—C10	1.513 (4)
O1—C7	1.375 (3)	C9—H9A	0.9700
O1—C8	1.378 (3)	C9—H9B	0.9700
O2—C10	1.329 (4)	C11—C12	1.495 (6)
O2—C11	1.458 (4)	C11—H11A	0.9700
O3—C10	1.197 (4)	C11—H11B	0.9700
C1—C8	1.347 (4)	C12—C13	1.480 (7)
C1—C2	1.443 (4)	C12—H12A	0.9700
C2—C3	1.397 (4)	C12—H12B	0.9700
C2—C7	1.399 (4)	C13—H13A	0.9600
C3—C4	1.380 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.400 (4)	C14—H14A	0.9600
C5—C6	1.381 (4)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
O4—S—C1	106.92 (14)	C10—C9—H9A	109.1
O4—S—C14	106.66 (17)	C8—C9—H9B	109.1
C1—S—C14	98.06 (16)	C10—C9—H9B	109.1
C7—O1—C8	106.0 (2)	H9A—C9—H9B	107.9
C10—O2—C11	116.8 (3)	O3—C10—O2	124.3 (3)
C8—C1—C2	107.3 (3)	O3—C10—C9	125.7 (3)
C8—C1—S	123.9 (2)	O2—C10—C9	110.0 (3)
C2—C1—S	128.7 (2)	O2—C11—C12	107.4 (3)
C3—C2—C7	119.1 (3)	O2—C11—H11A	110.2
C3—C2—C1	136.3 (3)	C12—C11—H11A	110.2
C7—C2—C1	104.6 (2)	O2—C11—H11B	110.2
C4—C3—C2	117.2 (3)	C12—C11—H11B	110.2
C4—C3—H3	121.4	H11A—C11—H11B	108.5
C2—C3—H3	121.4	C13—C12—C11	113.5 (4)
C3—C4—C5	123.1 (3)	C13—C12—H12A	108.9
C3—C4—I	118.6 (2)	C11—C12—H12A	108.9
C5—C4—I	118.3 (2)	C13—C12—H12B	108.9
C6—C5—C4	119.9 (3)	C11—C12—H12B	108.9
C6—C5—H5	120.1	H12A—C12—H12B	107.7
C4—C5—H5	120.1	C12—C13—H13A	109.5
C7—C6—C5	117.2 (3)	C12—C13—H13B	109.5
C7—C6—H6	121.4	H13A—C13—H13B	109.5
C5—C6—H6	121.4	C12—C13—H13C	109.5
O1—C7—C6	125.8 (3)	H13A—C13—H13C	109.5
O1—C7—C2	110.7 (3)	H13B—C13—H13C	109.5
C6—C7—C2	123.6 (3)	S—C14—H14A	109.5
C1—C8—O1	111.4 (3)	S—C14—H14B	109.5
C1—C8—C9	133.3 (3)	H14A—C14—H14B	109.5
O1—C8—C9	115.2 (2)	S—C14—H14C	109.5
C8—C9—C10	112.3 (2)	H14A—C14—H14C	109.5
C8—C9—H9A	109.1	H14B—C14—H14C	109.5
O4—S—C1—C8	−135.7 (3)	C3—C2—C7—O1	178.3 (2)
C14—S—C1—C8	114.1 (3)	C1—C2—C7—O1	−1.5 (3)
O4—S—C1—C2	40.8 (3)	C3—C2—C7—C6	−1.4 (4)
C14—S—C1—C2	−69.4 (3)	C1—C2—C7—C6	178.8 (3)
C8—C1—C2—C3	−178.7 (3)	C2—C1—C8—O1	−0.3 (3)
S—C1—C2—C3	4.4 (5)	S—C1—C8—O1	176.8 (2)
C8—C1—C2—C7	1.0 (3)	C2—C1—C8—C9	175.8 (3)
S—C1—C2—C7	−175.9 (2)	S—C1—C8—C9	−7.1 (5)
C7—C2—C3—C4	0.8 (4)	C7—O1—C8—C1	−0.6 (3)
C1—C2—C3—C4	−179.4 (3)	C7—O1—C8—C9	−177.5 (2)
C2—C3—C4—C5	0.4 (4)	C1—C8—C9—C10	−74.2 (4)
C2—C3—C4—I	−180.0 (2)	O1—C8—C9—C10	101.8 (3)
C3—C4—C5—C6	−1.2 (5)	C11—O2—C10—O3	−2.4 (5)
I—C4—C5—C6	179.2 (2)	C11—O2—C10—C9	179.2 (3)
C4—C5—C6—C7	0.7 (4)	C8—C9—C10—O3	22.6 (5)
C8—O1—C7—C6	−179.0 (3)	C8—C9—C10—O2	−159.0 (3)
C8—O1—C7—C2	1.3 (3)	C10—O2—C11—C12	169.5 (4)
C5—C6—C7—O1	−179.1 (3)	O2—C11—C12—C13	−63.9 (6)
C5—C6—C7—C2	0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg1i	0.97	3.12	3.814 (4)	130
C12—H12B···Cg2ii	0.97	2.99	3.929 (3)	162
C3—H3···O4iii	0.93	2.60	3.468 (4)	157
C9—H9B···O4iv	0.97	2.40	3.356 (4)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg1i	0.97	3.12	3.814 (4)	130
C12—H12B⋯Cg2ii	0.97	2.99	3.929 (3)	162
C3—H3⋯O4iii	0.93	2.60	3.468 (4)	157
C9—H9B⋯O4iv	0.97	2.40	3.356 (4)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively.