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

In the title compound, 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. The crystal structure is stabilized by weak inter-molecular C-H⋯π inter-actions between a methyl H atom of the methyl-sulfinyl group and the benzene ring of the benzofuran system, and by an I⋯O halogen bond of 3.173 (3) Å and a nearly linear C-I⋯O angle of 171.7 (1)°. In addition, the crystal structure exhibits weak inter-molecular C-H⋯O hydrogen bonds. The O atom of the carbonyl group and the butyl chain are both disordered over two positions with site-occupancy factors from refinement of 0.55 (4) and 0.45 (4) (for the O atom), and 0.76 (2) and 0.24 (2) (for the butyl group).

Related literature

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

Experimental

Crystal data

C15H17IO4S

M = 420.25

Monoclinic,

a = 10.298 (1) Å

b = 15.208 (1) Å

c = 11.109 (1) Å

β = 100.669 (1)°

V = 1709.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.01 mm−1

T = 100 (2) K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.673, T max = 0.822

8829 measured reflections

3009 independent reflections

2581 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.07

3009 reflections

222 parameters

43 restraints

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.61 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/S1600536809000208/hg2458sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000208/hg2458Isup2.hkl

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

C15H17IO4S	F(000) = 832
Mr = 420.25	Dx = 1.633 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2yn	Cell parameters from 5617 reflections
a = 10.298 (1) Å	θ = 2.3–28.1°
b = 15.208 (1) Å	µ = 2.01 mm−1
c = 11.109 (1) Å	T = 100 K
β = 100.669 (1)°	Block, colorless
V = 1709.7 (3) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	3009 independent reflections
Radiation source: fine-focus sealed tube	2581 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.3°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −11→18
Tmin = 0.673, Tmax = 0.822	l = −13→13
8829 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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F2) = 0.085	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0408P)2 + 1.6213P] where P = (Fo2 + 2Fc2)/3
3009 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.71 e Å−3
43 restraints	Δρmin = −0.61 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	Occ. (<1)
I	0.98000 (3)	0.639217 (19)	0.38449 (3)	0.07282 (14)
S	0.60101 (8)	0.31517 (5)	0.45617 (8)	0.0460 (2)
O1	0.4557 (2)	0.45536 (17)	0.1655 (2)	0.0562 (6)
O2	0.1138 (3)	0.3286 (2)	0.2161 (3)	0.0849 (10)
O3A	0.2384 (15)	0.4110 (13)	0.3619 (13)	0.074 (3)	0.55 (4)
O3B	0.2198 (16)	0.4365 (10)	0.323 (2)	0.075 (4)	0.45 (4)
O4	0.7434 (2)	0.29309 (16)	0.4707 (2)	0.0588 (6)
C1	0.5648 (3)	0.3928 (2)	0.3367 (3)	0.0411 (7)
C2	0.6417 (3)	0.4674 (2)	0.3106 (3)	0.0404 (7)
C3	0.7603 (3)	0.5070 (2)	0.3653 (3)	0.0438 (7)
H3	0.8119	0.4843	0.4384	0.053*
C4	0.7992 (3)	0.5803 (2)	0.3085 (3)	0.0520 (8)
C5	0.7244 (4)	0.6150 (3)	0.2018 (4)	0.0651 (10)
H5	0.7551	0.6657	0.1658	0.078*
C6	0.6077 (4)	0.5773 (3)	0.1483 (3)	0.0628 (10)
H6	0.5555	0.6009	0.0760	0.075*
C7	0.5693 (3)	0.5030 (2)	0.2046 (3)	0.0492 (8)
C8	0.4576 (3)	0.3885 (2)	0.2479 (3)	0.0474 (8)
C9	0.3408 (3)	0.3292 (3)	0.2250 (4)	0.0581 (9)
H9A	0.3645	0.2724	0.2668	0.070*
H9B	0.3165	0.3176	0.1360	0.070*
C10	0.2236 (4)	0.3677 (3)	0.2695 (4)	0.0609 (10)
C12	−0.1176 (4)	0.3369 (5)	0.1516 (6)	0.121 (2)
H12A	−0.1186	0.2744	0.1266	0.145*	0.759 (19)
H12B	−0.2018	0.3484	0.1796	0.145*	0.759 (19)
H12C	−0.0930	0.2748	0.1415	0.145*	0.241 (19)
H12D	−0.2016	0.3407	0.1825	0.145*	0.241 (19)
C13	−0.1166 (8)	0.3909 (7)	0.0415 (9)	0.180 (4)
H13A	−0.0364	0.3789	0.0069	0.216*	0.759 (19)
H13B	−0.1186	0.4543	0.0614	0.216*	0.759 (19)
H13C	−0.0345	0.3687	0.0178	0.216*	0.241 (19)
H13D	−0.0905	0.4483	0.0808	0.216*	0.241 (19)
C11A	−0.0090 (6)	0.3482 (8)	0.2583 (7)	0.077 (2)	0.759 (19)
H11A	−0.0077	0.4093	0.2894	0.092*	0.759 (19)
H11B	−0.0208	0.3077	0.3251	0.092*	0.759 (19)
C14A	−0.2370 (12)	0.3655 (11)	−0.0466 (14)	0.175 (6)	0.759 (19)
H14A	−0.3089	0.4062	−0.0392	0.263*	0.759 (19)
H14B	−0.2627	0.3056	−0.0286	0.263*	0.759 (19)
H14C	−0.2191	0.3679	−0.1301	0.263*	0.759 (19)
C11B	−0.0098 (17)	0.3900 (18)	0.223 (3)	0.077 (7)	0.241 (19)
H11C	−0.0222	0.3983	0.3089	0.093*	0.241 (19)
H11D	−0.0017	0.4480	0.1851	0.093*	0.241 (19)
C14B	−0.185 (4)	0.424 (3)	−0.0790 (17)	0.141 (14)	0.241 (19)
H14D	−0.2681	0.3920	−0.1041	0.211*	0.241 (19)
H14E	−0.1284	0.4149	−0.1399	0.211*	0.241 (19)
H14F	−0.2034	0.4869	−0.0728	0.211*	0.241 (19)
C15	0.5826 (5)	0.3860 (3)	0.5804 (3)	0.0654 (10)
H15A	0.6071	0.3541	0.6579	0.098*
H15B	0.4904	0.4053	0.5705	0.098*
H15C	0.6400	0.4374	0.5807	0.098*

	U11	U22	U33	U12	U13	U23
I	0.06107 (19)	0.0672 (2)	0.0881 (2)	−0.02167 (12)	0.00823 (14)	0.01316 (14)
S	0.0464 (4)	0.0356 (4)	0.0542 (5)	−0.0007 (3)	0.0051 (4)	−0.0015 (3)
O1	0.0494 (13)	0.0693 (16)	0.0437 (13)	0.0025 (12)	−0.0075 (10)	−0.0056 (12)
O2	0.0446 (14)	0.110 (2)	0.097 (2)	−0.0015 (15)	0.0058 (14)	−0.053 (2)
O3A	0.072 (5)	0.087 (6)	0.064 (5)	−0.013 (5)	0.016 (4)	−0.030 (4)
O3B	0.069 (5)	0.068 (5)	0.088 (7)	0.000 (4)	0.014 (5)	−0.030 (5)
O4	0.0513 (14)	0.0568 (15)	0.0648 (15)	0.0124 (11)	0.0019 (11)	0.0010 (12)
C1	0.0395 (16)	0.0378 (15)	0.0440 (17)	0.0028 (13)	0.0030 (13)	−0.0046 (13)
C2	0.0405 (16)	0.0447 (17)	0.0350 (15)	0.0049 (13)	0.0045 (12)	−0.0031 (13)
C3	0.0431 (17)	0.0464 (18)	0.0406 (16)	0.0009 (14)	0.0044 (13)	0.0022 (14)
C4	0.0506 (19)	0.052 (2)	0.053 (2)	−0.0045 (16)	0.0100 (15)	0.0052 (16)
C5	0.075 (3)	0.062 (2)	0.060 (2)	−0.003 (2)	0.015 (2)	0.0218 (19)
C6	0.069 (2)	0.075 (3)	0.0423 (19)	0.006 (2)	0.0048 (17)	0.0150 (18)
C7	0.0499 (19)	0.057 (2)	0.0394 (17)	0.0066 (16)	0.0057 (14)	−0.0018 (15)
C8	0.0426 (17)	0.0495 (18)	0.0475 (18)	0.0035 (14)	0.0013 (14)	−0.0100 (15)
C9	0.0427 (18)	0.057 (2)	0.069 (2)	0.0006 (16)	−0.0049 (16)	−0.0229 (18)
C10	0.051 (2)	0.065 (2)	0.066 (2)	−0.0061 (17)	0.0064 (18)	−0.0211 (19)
C12	0.053 (3)	0.160 (6)	0.149 (6)	0.002 (3)	0.021 (3)	−0.065 (5)
C13	0.152 (8)	0.215 (10)	0.166 (9)	0.103 (8)	0.010 (7)	0.029 (8)
C11A	0.049 (3)	0.095 (6)	0.087 (4)	0.004 (3)	0.016 (3)	−0.018 (4)
C14A	0.148 (8)	0.195 (10)	0.167 (9)	0.043 (7)	−0.010 (7)	−0.002 (7)
C11B	0.064 (9)	0.088 (11)	0.084 (11)	0.011 (8)	0.023 (8)	−0.007 (8)
C14B	0.142 (16)	0.142 (16)	0.139 (16)	0.015 (10)	0.027 (10)	0.012 (9)
C15	0.090 (3)	0.058 (2)	0.051 (2)	0.010 (2)	0.022 (2)	−0.0034 (18)

I—C4	2.098 (4)	C9—H9B	0.9900
I—O4i	13.531 (3)	C12—C13	1.476 (11)
S—O4	1.484 (2)	C12—C11B	1.480 (2)
S—C1	1.764 (3)	C12—C11A	1.481 (2)
S—C15	1.788 (4)	C12—H12A	0.9900
O1—C8	1.366 (4)	C12—H12B	0.9900
O1—C7	1.376 (4)	C12—H12C	0.9900
O2—C10	1.317 (5)	C12—H12D	0.9900
O2—C11A	1.459 (7)	C13—C14B	1.4797 (15)
O2—C11B	1.59 (3)	C13—C14A	1.481 (2)
O3A—O3B	0.590 (16)	C13—H13A	0.9900
O3A—C10	1.205 (5)	C13—H13B	0.9900
O3B—C10	1.205 (5)	C13—H13C	0.9900
C1—C8	1.339 (4)	C13—H13D	0.9900
C1—C2	1.444 (4)	C11A—H11A	0.9900
C2—C7	1.383 (4)	C11A—H11B	0.9900
C2—C3	1.395 (4)	C14A—H14A	0.9800
C3—C4	1.377 (5)	C14A—H14B	0.9800
C3—H3	0.9500	C14A—H14C	0.9800
C4—C5	1.392 (5)	C11B—H11C	0.9900
C5—C6	1.364 (6)	C11B—H11D	0.9900
C5—H5	0.9500	C14B—H14D	0.9800
C6—C7	1.384 (5)	C14B—H14E	0.9800
C6—H6	0.9500	C14B—H14F	0.9800
C8—C9	1.486 (5)	C15—H15A	0.9800
C9—C10	1.505 (5)	C15—H15B	0.9800
C9—H9A	0.9900	C15—H15C	0.9800
C4—I—O4i	52.14 (10)	C11B—C12—H12C	113.6
O4—S—C1	107.46 (15)	C11A—C12—H12C	91.8
O4—S—C15	107.26 (19)	H12B—C12—H12C	117.5
C1—S—C15	98.03 (17)	C13—C12—H12D	113.3
C8—O1—C7	106.0 (2)	C11B—C12—H12D	113.4
C10—O2—C11A	119.1 (4)	C11A—C12—H12D	107.1
C10—O2—C11B	109.9 (4)	H12A—C12—H12D	100.9
O3B—O3A—C10	75.8 (4)	H12C—C12—H12D	110.7
O3A—O3B—C10	75.8 (4)	C12—C13—C14B	149.8 (19)
C8—C1—C2	107.4 (3)	C12—C13—C14A	105.6 (10)
C8—C1—S	123.5 (3)	C12—C13—H13A	110.6
C2—C1—S	129.1 (2)	C14B—C13—H13A	90.2
C7—C2—C3	119.5 (3)	C14A—C13—H13A	110.6
C7—C2—C1	104.4 (3)	C12—C13—H13B	110.6
C3—C2—C1	136.0 (3)	C14B—C13—H13B	81.2
C4—C3—C2	117.1 (3)	C14A—C13—H13B	110.6
C4—C3—H3	121.5	H13A—C13—H13B	108.8
C2—C3—H3	121.5	C12—C13—H13C	99.6
C3—C4—C5	122.3 (3)	C14B—C13—H13C	99.4
C3—C4—I	118.3 (2)	C14A—C13—H13C	112.8
C5—C4—I	119.4 (3)	H13B—C13—H13C	116.6
C6—C5—C4	121.1 (4)	C12—C13—H13D	99.6
C6—C5—H5	119.4	C14B—C13—H13D	98.4
C4—C5—H5	119.4	C14A—C13—H13D	130.3
C5—C6—C7	116.6 (3)	H13A—C13—H13D	99.0
C5—C6—H6	121.7	H13C—C13—H13D	104.1
C7—C6—H6	121.7	O2—C11A—C12	106.9 (5)
O1—C7—C2	110.8 (3)	O2—C11A—H11A	110.3
O1—C7—C6	125.8 (3)	C12—C11A—H11A	110.3
C2—C7—C6	123.4 (3)	O2—C11A—H11B	110.3
C1—C8—O1	111.4 (3)	C12—C11A—H11B	110.3
C1—C8—C9	133.4 (3)	H11A—C11A—H11B	108.6
O1—C8—C9	115.2 (3)	C13—C14A—H14A	109.5
C8—C9—C10	112.4 (3)	C13—C14A—H14B	109.5
C8—C9—H9A	109.1	C13—C14A—H14C	109.5
C10—C9—H9A	109.1	C12—C11B—O2	100.4 (12)
C8—C9—H9B	109.1	C12—C11B—H11C	111.7
C10—C9—H9B	109.1	O2—C11B—H11C	111.7
H9A—C9—H9B	107.9	C12—C11B—H11D	111.7
O3A—C10—O2	126.3 (7)	O2—C11B—H11D	111.7
O3B—C10—O2	120.6 (9)	H11C—C11B—H11D	109.5
O3A—C10—C9	120.6 (8)	C13—C14B—H14D	109.5
O3B—C10—C9	126.7 (9)	C13—C14B—H14E	109.5
O2—C10—C9	110.5 (3)	H14D—C14B—H14E	109.5
C13—C12—C11B	91.3 (16)	C13—C14B—H14F	109.5
C13—C12—C11A	118.6 (8)	H14D—C14B—H14F	109.5
C13—C12—H12A	107.7	H14E—C14B—H14F	109.5
C11B—C12—H12A	130.0	S—C15—H15A	109.5
C11A—C12—H12A	107.7	S—C15—H15B	109.5
C13—C12—H12B	107.7	H15A—C15—H15B	109.5
C11B—C12—H12B	110.4	S—C15—H15C	109.5
C11A—C12—H12B	107.7	H15A—C15—H15C	109.5
H12A—C12—H12B	107.1	H15B—C15—H15C	109.5
C13—C12—H12C	113.4
O4—S—C1—C8	135.5 (3)	C7—O1—C8—C1	0.9 (4)
C15—S—C1—C8	−113.5 (3)	C7—O1—C8—C9	178.5 (3)
O4—S—C1—C2	−41.2 (3)	C1—C8—C9—C10	96.8 (5)
C15—S—C1—C2	69.8 (3)	O1—C8—C9—C10	−80.1 (4)
C8—C1—C2—C7	0.7 (3)	O3B—O3A—C10—O2	−88 (3)
S—C1—C2—C7	177.8 (3)	O3B—O3A—C10—C9	112 (3)
C8—C1—C2—C3	179.9 (4)	O3A—O3B—C10—O2	111 (3)
S—C1—C2—C3	−3.0 (5)	O3A—O3B—C10—C9	−87 (3)
C7—C2—C3—C4	−0.5 (4)	C11A—O2—C10—O3A	10.1 (16)
C1—C2—C3—C4	−179.6 (3)	C11B—O2—C10—O3A	39 (2)
C2—C3—C4—C5	0.5 (5)	C11A—O2—C10—O3B	−23.3 (17)
C2—C3—C4—I	−178.0 (2)	C11B—O2—C10—O3B	6(2)
O4i—I—C4—C3	55.4 (2)	C11A—O2—C10—C9	172.1 (6)
O4i—I—C4—C5	−123.1 (4)	C11B—O2—C10—C9	−159.0 (14)
C3—C4—C5—C6	0.1 (6)	C8—C9—C10—O3A	−36.2 (13)
I—C4—C5—C6	178.6 (3)	C8—C9—C10—O3B	−2.8 (18)
C4—C5—C6—C7	−0.7 (6)	C8—C9—C10—O2	160.6 (4)
C8—O1—C7—C2	−0.4 (4)	C11B—C12—C13—C14B	−158 (4)
C8—O1—C7—C6	−179.7 (3)	C11A—C12—C13—C14B	−168 (3)
C3—C2—C7—O1	−179.6 (3)	C11B—C12—C13—C14A	−168.6 (12)
C1—C2—C7—O1	−0.2 (3)	C11A—C12—C13—C14A	−179.2 (8)
C3—C2—C7—C6	−0.2 (5)	C10—O2—C11A—C12	150.7 (6)
C1—C2—C7—C6	179.1 (3)	C11B—O2—C11A—C12	73.5 (9)
C5—C6—C7—O1	−180.0 (3)	C13—C12—C11A—O2	−59.2 (10)
C5—C6—C7—C2	0.8 (6)	C11B—C12—C11A—O2	−81 (2)
C2—C1—C8—O1	−1.0 (4)	C13—C12—C11B—O2	−98.9 (16)
S—C1—C8—O1	−178.3 (2)	C11A—C12—C11B—O2	62 (2)
C2—C1—C8—C9	−178.0 (3)	C10—O2—C11B—C12	176.1 (12)
S—C1—C8—C9	4.6 (5)	C11A—O2—C11B—C12	−69.0 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···Cgii	0.98	2.97	3.722 (4)	134
C5—H5···O4iii	0.95	2.46	3.370 (4)	160
C9—H9B···O4iv	0.99	2.50	3.376 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯Cgi	0.98	2.97	3.722 (4)	134
C5—H5⋯O4ii	0.95	2.46	3.370 (4)	160
C9—H9B⋯O4iii	0.99	2.50	3.376 (4)	147

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the C2–C7 benzene ring.