5-Chloro-3-ethyl-sulfinyl-2-(4-iodo-phen-yl)-7-methyl-1-benzofuran.

In the title compound, C(17)H(14)ClIO(2)S, the 4-iodo-phenyl ring makes a dihedral angle of 1.61 (9)° with the benzofuran ring system. In the crystal, mol-ecules are linked through a weak inter-molecular C-H⋯O hydrogen bond and an I⋯O contact [3.416 (2) Å]. The ethyl group is disordered over two orientations with site-occupancy factors of 0.402 (7) and 0.598 (7).

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the structures of related 3-ethyl­sulfinyl-2-(4-iodo­phen­yl)-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H14ClIO2S

M = 444.69

Triclinic,

a = 7.8013 (2) Å

b = 10.4240 (3) Å

c = 11.6003 (3) Å

α = 115.962 (1)°

β = 98.040 (1)°

γ = 96.661 (1)°

V = 823.00 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.24 mm−1

T = 173 K

0.48 × 0.34 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.473, T max = 0.746

14721 measured reflections

3773 independent reflections

3408 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.065

S = 1.06

3773 reflections

221 parameters

28 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S160053681003134X/is2588sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003134X/is2588Isup2.hkl

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

C17H14ClIO2S	Z = 2
Mr = 444.69	F(000) = 436
Triclinic, P1	Dx = 1.794 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8013 (2) Å	Cell parameters from 9231 reflections
b = 10.4240 (3) Å	θ = 2.2–27.5°
c = 11.6003 (3) Å	µ = 2.24 mm−1
α = 115.962 (1)°	T = 173 K
β = 98.040 (1)°	Block, colourless
γ = 96.661 (1)°	0.48 × 0.34 × 0.16 mm
V = 823.00 (4) Å3

Bruker SMART APEXII CCD diffractometer	3773 independent reflections
Radiation source: rotating anode	3408 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.473, Tmax = 0.746	l = −15→15
14721 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)] = 0.024	Hydrogen site location: difference Fourier map
wR(F2) = 0.065	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.034P)2 + 0.2748P] where P = (Fo2 + 2Fc2)/3
3773 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.28 e Å−3
28 restraints	Δρmin = −0.60 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	0.64468 (2)	0.843070 (18)	0.633828 (13)	0.05745 (7)
Cl	−0.13606 (8)	0.12905 (7)	−0.54903 (5)	0.06029 (16)
S	0.05956 (8)	0.20738 (7)	0.00343 (6)	0.05340 (14)
O1	0.26320 (19)	0.55334 (15)	−0.03279 (13)	0.0397 (3)
O2	−0.1151 (3)	0.1273 (2)	−0.0800 (2)	0.0830 (7)
C3	−0.0084 (3)	0.2242 (2)	−0.2921 (2)	0.0432 (4)
H3	−0.0663	0.1352	−0.3031	0.052*
C1	0.1344 (3)	0.3441 (2)	−0.04020 (19)	0.0398 (4)
C2	0.0905 (3)	0.3316 (2)	−0.17052 (19)	0.0383 (4)
C4	−0.0153 (3)	0.2577 (2)	−0.3946 (2)	0.0440 (4)
C5	0.0668 (3)	0.3905 (2)	−0.3815 (2)	0.0450 (5)
H5	0.0567	0.4065	−0.4547	0.054*
C6	0.1637 (3)	0.4998 (2)	−0.2612 (2)	0.0413 (4)
C7	0.1723 (3)	0.4632 (2)	−0.15913 (18)	0.0377 (4)
C8	0.2378 (3)	0.4790 (2)	0.03875 (18)	0.0384 (4)
C9	0.3273 (3)	0.5601 (2)	0.17695 (19)	0.0396 (4)
C10	0.3167 (3)	0.5045 (3)	0.2654 (2)	0.0498 (5)
H10	0.2503	0.4120	0.2370	0.060*
C11	0.4045 (3)	0.5857 (3)	0.3958 (2)	0.0512 (5)
H11	0.3943	0.5481	0.4545	0.061*
C12	0.5061 (3)	0.7208 (2)	0.4386 (2)	0.0446 (5)
C13	0.5151 (4)	0.7794 (3)	0.3532 (2)	0.0611 (7)
H13	0.5815	0.8721	0.3825	0.073*
C14	0.4253 (4)	0.7001 (3)	0.2240 (2)	0.0590 (6)
H14	0.4303	0.7410	0.1673	0.071*
C15	0.2513 (4)	0.6454 (3)	−0.2418 (3)	0.0580 (6)
H15A	0.3745	0.6468	−0.2421	0.087*
H15B	0.2385	0.7197	−0.1593	0.087*
H15C	0.1971	0.6631	−0.3116	0.087*
C16A	0.2618 (6)	0.1332 (6)	0.0089 (5)	0.0561 (19)	0.402 (7)
H16A	0.3649	0.2108	0.0570	0.067*	0.402 (7)
H16B	0.2543	0.0697	0.0498	0.067*	0.402 (7)
C17A	0.2695 (15)	0.0509 (8)	−0.1310 (5)	0.074 (2)	0.402 (7)
H17A	0.1592	−0.0159	−0.1789	0.112*	0.402 (7)
H17B	0.3633	−0.0024	−0.1382	0.112*	0.402 (7)
H17C	0.2909	0.1174	−0.1665	0.112*	0.402 (7)
C16B	0.1842 (6)	0.0735 (5)	−0.0927 (4)	0.0586 (13)	0.598 (7)
H16C	0.1382	−0.0208	−0.0998	0.070*	0.598 (7)
H16D	0.1686	0.0643	−0.1806	0.070*	0.598 (7)
C17B	0.3749 (6)	0.1176 (7)	−0.0305 (6)	0.0832 (18)	0.598 (7)
H17D	0.4174	0.2156	−0.0140	0.125*	0.598 (7)
H17E	0.4386	0.0533	−0.0882	0.125*	0.598 (7)
H17F	0.3920	0.1126	0.0508	0.125*	0.598 (7)

	U11	U22	U33	U12	U13	U23
I	0.05606 (11)	0.06525 (12)	0.03984 (9)	−0.00242 (7)	−0.00008 (6)	0.02082 (7)
Cl	0.0624 (3)	0.0565 (3)	0.0396 (3)	0.0026 (3)	0.0005 (2)	0.0076 (2)
S	0.0596 (3)	0.0483 (3)	0.0604 (3)	0.0012 (3)	0.0147 (3)	0.0339 (3)
O1	0.0480 (7)	0.0332 (7)	0.0359 (7)	0.0025 (6)	0.0051 (5)	0.0165 (5)
O2	0.0949 (15)	0.0656 (12)	0.0693 (12)	−0.0320 (11)	−0.0043 (11)	0.0322 (10)
C3	0.0463 (10)	0.0333 (10)	0.0431 (10)	0.0038 (8)	0.0085 (8)	0.0130 (8)
C1	0.0467 (10)	0.0359 (10)	0.0403 (10)	0.0077 (8)	0.0110 (8)	0.0202 (8)
C2	0.0414 (10)	0.0341 (9)	0.0392 (9)	0.0078 (8)	0.0097 (8)	0.0163 (8)
C4	0.0418 (10)	0.0425 (11)	0.0356 (9)	0.0073 (8)	0.0036 (8)	0.0090 (8)
C5	0.0496 (11)	0.0497 (12)	0.0378 (10)	0.0118 (9)	0.0089 (8)	0.0218 (9)
C6	0.0459 (10)	0.0390 (10)	0.0428 (10)	0.0083 (8)	0.0113 (8)	0.0217 (8)
C7	0.0404 (9)	0.0343 (9)	0.0358 (9)	0.0059 (7)	0.0067 (7)	0.0146 (7)
C8	0.0446 (10)	0.0359 (10)	0.0387 (9)	0.0088 (8)	0.0107 (8)	0.0199 (8)
C9	0.0414 (10)	0.0376 (10)	0.0379 (9)	0.0068 (8)	0.0071 (7)	0.0163 (8)
C10	0.0586 (13)	0.0419 (11)	0.0452 (11)	−0.0001 (10)	0.0009 (9)	0.0222 (9)
C11	0.0588 (13)	0.0525 (13)	0.0437 (11)	0.0043 (10)	0.0028 (9)	0.0273 (10)
C12	0.0428 (10)	0.0503 (12)	0.0363 (9)	0.0061 (9)	0.0046 (8)	0.0179 (9)
C13	0.0743 (16)	0.0502 (13)	0.0463 (12)	−0.0156 (12)	−0.0007 (11)	0.0216 (10)
C14	0.0800 (16)	0.0503 (13)	0.0409 (11)	−0.0101 (12)	0.0022 (11)	0.0246 (10)
C15	0.0709 (15)	0.0502 (13)	0.0551 (13)	−0.0005 (11)	0.0093 (11)	0.0306 (11)
C16A	0.076 (4)	0.041 (3)	0.050 (3)	0.005 (3)	0.002 (3)	0.025 (3)
C17A	0.112 (6)	0.057 (4)	0.062 (4)	0.028 (4)	0.015 (4)	0.033 (3)
C16B	0.084 (3)	0.044 (2)	0.051 (3)	0.017 (2)	0.019 (2)	0.0216 (19)
C17B	0.081 (4)	0.094 (4)	0.099 (4)	0.037 (3)	0.035 (3)	0.057 (3)

I—C12	2.095 (2)	C10—C11	1.389 (3)
I—O2i	3.416 (2)	C10—H10	0.9300
Cl—C4	1.739 (2)	C11—C12	1.370 (3)
S—O2	1.466 (2)	C11—H11	0.9300
S—C1	1.774 (2)	C12—C13	1.378 (3)
S—C16A	1.841 (4)	C13—C14	1.381 (3)
S—C16B	1.842 (4)	C13—H13	0.9300
O1—C7	1.372 (2)	C14—H14	0.9300
O1—C8	1.379 (2)	C15—H15A	0.9600
C3—C4	1.374 (3)	C15—H15B	0.9600
C3—C2	1.397 (3)	C15—H15C	0.9600
C3—H3	0.9300	C16A—C17A	1.4807 (15)
C1—C8	1.368 (3)	C16A—H16A	0.9700
C1—C2	1.447 (3)	C16A—H16B	0.9700
C2—C7	1.386 (3)	C17A—H17A	0.9600
C4—C5	1.390 (3)	C17A—H17B	0.9600
C5—C6	1.389 (3)	C17A—H17C	0.9600
C5—H5	0.9300	C16B—C17B	1.4812 (15)
C6—C7	1.391 (3)	C16B—H16C	0.9700
C6—C15	1.495 (3)	C16B—H16D	0.9700
C8—C9	1.461 (3)	C17B—H17D	0.9600
C9—C10	1.389 (3)	C17B—H17E	0.9600
C9—C14	1.392 (3)	C17B—H17F	0.9600
C12—I—O2i	161.46 (7)	C12—C11—C10	120.4 (2)
O2—S—C1	108.18 (11)	C12—C11—H11	119.8
O2—S—C16A	126.7 (2)	C10—C11—H11	119.8
C1—S—C16A	99.2 (2)	C11—C12—C13	119.9 (2)
O2—S—C16B	96.09 (17)	C11—C12—I	121.10 (16)
C1—S—C16B	96.62 (17)	C13—C12—I	119.02 (16)
C7—O1—C8	106.81 (15)	C12—C13—C14	119.8 (2)
C4—C3—C2	116.20 (19)	C12—C13—H13	120.1
C4—C3—H3	121.9	C14—C13—H13	120.1
C2—C3—H3	121.9	C13—C14—C9	121.3 (2)
C8—C1—C2	106.99 (17)	C13—C14—H14	119.3
C8—C1—S	128.36 (16)	C9—C14—H14	119.3
C2—C1—S	124.63 (15)	C6—C15—H15A	109.5
C7—C2—C3	119.59 (18)	C6—C15—H15B	109.5
C7—C2—C1	105.15 (16)	H15A—C15—H15B	109.5
C3—C2—C1	135.26 (19)	C6—C15—H15C	109.5
C3—C4—C5	123.51 (19)	H15A—C15—H15C	109.5
C3—C4—Cl	118.70 (17)	H15B—C15—H15C	109.5
C5—C4—Cl	117.78 (17)	C17A—C16A—S	103.8 (4)
C6—C5—C4	121.43 (19)	C17A—C16A—H16A	111.0
C6—C5—H5	119.3	S—C16A—H16A	111.0
C4—C5—H5	119.3	C17A—C16A—H16B	111.0
C5—C6—C7	114.33 (19)	S—C16A—H16B	111.0
C5—C6—C15	123.3 (2)	H16A—C16A—H16B	109.0
C7—C6—C15	122.3 (2)	C17B—C16B—S	111.2 (3)
O1—C7—C2	110.77 (17)	C17B—C16B—H16C	109.4
O1—C7—C6	124.31 (18)	S—C16B—H16C	109.4
C2—C7—C6	124.93 (18)	C17B—C16B—H16D	109.4
C1—C8—O1	110.28 (16)	S—C16B—H16D	109.4
C1—C8—C9	135.71 (19)	H16C—C16B—H16D	108.0
O1—C8—C9	114.00 (16)	C16B—C17B—H17D	109.5
C10—C9—C14	117.86 (19)	C16B—C17B—H17E	109.5
C10—C9—C8	122.76 (19)	H17D—C17B—H17E	109.5
C14—C9—C8	119.37 (19)	C16B—C17B—H17F	109.5
C9—C10—C11	120.6 (2)	H17D—C17B—H17F	109.5
C9—C10—H10	119.7	H17E—C17B—H17F	109.5
C11—C10—H10	119.7
O2—S—C1—C8	147.2 (2)	C2—C1—C8—O1	−0.2 (2)
C16A—S—C1—C8	−79.1 (3)	S—C1—C8—O1	−178.82 (15)
C16B—S—C1—C8	−114.1 (2)	C2—C1—C8—C9	−179.1 (2)
O2—S—C1—C2	−31.1 (2)	S—C1—C8—C9	2.3 (4)
C16A—S—C1—C2	102.6 (2)	C7—O1—C8—C1	0.6 (2)
C16B—S—C1—C2	67.5 (2)	C7—O1—C8—C9	179.74 (16)
C4—C3—C2—C7	0.8 (3)	C1—C8—C9—C10	−1.6 (4)
C4—C3—C2—C1	−179.5 (2)	O1—C8—C9—C10	179.5 (2)
C8—C1—C2—C7	−0.2 (2)	C1—C8—C9—C14	179.6 (3)
S—C1—C2—C7	178.46 (15)	O1—C8—C9—C14	0.7 (3)
C8—C1—C2—C3	−179.9 (2)	C14—C9—C10—C11	−1.3 (4)
S—C1—C2—C3	−1.2 (4)	C8—C9—C10—C11	179.9 (2)
C2—C3—C4—C5	−1.2 (3)	C9—C10—C11—C12	−1.4 (4)
C2—C3—C4—Cl	180.00 (15)	C10—C11—C12—C13	2.9 (4)
C3—C4—C5—C6	0.3 (3)	C10—C11—C12—I	−178.48 (19)
Cl—C4—C5—C6	179.08 (17)	O2i—I—C12—C11	−167.99 (19)
C4—C5—C6—C7	1.0 (3)	O2i—I—C12—C13	10.6 (4)
C4—C5—C6—C15	−178.8 (2)	C11—C12—C13—C14	−1.6 (4)
C8—O1—C7—C2	−0.7 (2)	I—C12—C13—C14	179.7 (2)
C8—O1—C7—C6	179.17 (19)	C12—C13—C14—C9	−1.1 (4)
C3—C2—C7—O1	−179.68 (18)	C10—C9—C14—C13	2.5 (4)
C1—C2—C7—O1	0.6 (2)	C8—C9—C14—C13	−178.6 (3)
C3—C2—C7—C6	0.4 (3)	O2—S—C16A—C17A	48.1 (6)
C1—C2—C7—C6	−179.3 (2)	C1—S—C16A—C17A	−72.9 (5)
C5—C6—C7—O1	178.80 (18)	C16B—S—C16A—C17A	15.4 (5)
C15—C6—C7—O1	−1.5 (3)	O2—S—C16B—C17B	−177.3 (4)
C5—C6—C7—C2	−1.3 (3)	C1—S—C16B—C17B	73.5 (4)
C15—C6—C7—C2	178.4 (2)	C16A—S—C16B—C17B	−23.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C16A—H16B···O2ii	0.97	2.40	3.297 (6)	154.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16A—H16B⋯O2i	0.97	2.40	3.297 (6)	154

Symmetry code: (i) .