3-Cyclo-hexyl-sulfonyl-5-iodo-2,7-dimethyl-1-benzofuran.

In the title compound, C(16)H(19)IO(3)S, the cyclo-hexyl ring adopts a chair conformation. In the crystal, pairs of inter-molecular I⋯O contacts [3.269 (2) Å] link the mol-ecules into inversion dimers. These dimers are further stabilized by a slipped π-π inter-action between the benzene and furan rings of adjacent mol-ecules [centroid-centroid distance = 3.701 (3) Å, inter-planar distance = 3.372 (3) Å and slippage = 1.525 (3) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of related 3-cyclo­hexyl­sulfonyl-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011 ▶). For a review on halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H19IO3S

M = 418.27

Triclinic,

a = 6.8643 (2) Å

b = 8.4981 (2) Å

c = 14.2323 (3) Å

α = 102.512 (1)°

β = 99.846 (1)°

γ = 92.092 (1)°

V = 796.23 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.15 mm−1

T = 173 K

0.24 × 0.16 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.629, T max = 0.759

15021 measured reflections

3997 independent reflections

3753 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.058

S = 1.06

3997 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.63 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 datablock(s) global, I. DOI: 10.1107/S1600536811027395/zl2384sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027395/zl2384Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027395/zl2384Isup3.cml

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

C16H19IO3S	Z = 2
Mr = 418.27	F(000) = 416
Triclinic, P1	Dx = 1.745 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8643 (2) Å	Cell parameters from 8926 reflections
b = 8.4981 (2) Å	θ = 2.5–28.4°
c = 14.2323 (3) Å	µ = 2.15 mm−1
α = 102.512 (1)°	T = 173 K
β = 99.846 (1)°	Block, colourless
γ = 92.092 (1)°	0.24 × 0.16 × 0.14 mm
V = 796.23 (3) Å3

Bruker SMART APEXII CCD diffractometer	3997 independent reflections
Radiation source: rotating anode	3753 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.5°
φ and ω scans	h = −7→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.629, Tmax = 0.759	l = −19→18
15021 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)] = 0.023	Hydrogen site location: difference Fourier map
wR(F2) = 0.058	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0291P)2 + 0.2895P] where P = (Fo2 + 2Fc2)/3
3997 reflections	(Δ/σ)max = 0.003
192 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.63 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
I1	0.227778 (18)	0.565947 (15)	0.643317 (9)	0.02648 (5)
S1	0.19017 (7)	0.68116 (6)	0.21668 (4)	0.02476 (10)
O1	0.6820 (2)	0.89122 (16)	0.38987 (10)	0.0237 (3)
O2	0.0181 (2)	0.67742 (19)	0.26177 (12)	0.0329 (3)
O3	0.1832 (3)	0.76329 (19)	0.13777 (12)	0.0350 (4)
C1	0.3897 (3)	0.7652 (2)	0.30960 (14)	0.0224 (4)
C2	0.4132 (3)	0.7461 (2)	0.40933 (14)	0.0211 (4)
C3	0.3023 (3)	0.6713 (2)	0.46236 (14)	0.0234 (4)
H3	0.1761	0.6163	0.4336	0.028*
C4	0.3852 (3)	0.6808 (2)	0.55982 (14)	0.0229 (4)
C5	0.5707 (3)	0.7612 (2)	0.60332 (14)	0.0231 (4)
H5	0.6207	0.7642	0.6702	0.028*
C6	0.6829 (3)	0.8363 (2)	0.55159 (15)	0.0225 (4)
C7	0.5962 (3)	0.8262 (2)	0.45489 (14)	0.0211 (4)
C8	0.5545 (3)	0.8523 (2)	0.30207 (14)	0.0238 (4)
C9	0.8856 (3)	0.9191 (3)	0.59487 (16)	0.0278 (4)
H9A	0.9151	0.9214	0.6650	0.042*
H9B	0.8892	1.0300	0.5855	0.042*
H9C	0.9846	0.8600	0.5623	0.042*
C10	0.6225 (3)	0.9118 (3)	0.22258 (16)	0.0311 (4)
H10A	0.6478	1.0297	0.2421	0.047*
H10B	0.5201	0.8827	0.1633	0.047*
H10C	0.7449	0.8628	0.2094	0.047*
C11	0.2463 (3)	0.4764 (2)	0.17566 (14)	0.0252 (4)
H11	0.2952	0.4337	0.2349	0.030*
C12	0.0574 (3)	0.3736 (3)	0.11981 (17)	0.0342 (5)
H12A	−0.0438	0.3806	0.1622	0.041*
H12B	0.0030	0.4145	0.0614	0.041*
C13	0.1052 (4)	0.1980 (3)	0.0884 (2)	0.0461 (6)
H13A	0.1485	0.1550	0.1473	0.055*
H13B	−0.0160	0.1324	0.0500	0.055*
C14	0.2662 (4)	0.1825 (3)	0.0274 (2)	0.0446 (6)
H14A	0.2180	0.2151	−0.0346	0.054*
H14B	0.2979	0.0681	0.0112	0.054*
C15	0.4538 (4)	0.2879 (3)	0.08190 (18)	0.0365 (5)
H15A	0.5530	0.2811	0.0385	0.044*
H15B	0.5111	0.2470	0.1399	0.044*
C16	0.4094 (3)	0.4643 (3)	0.11478 (16)	0.0303 (4)
H16A	0.5310	0.5283	0.1541	0.036*
H16B	0.3672	0.5096	0.0567	0.036*

	U11	U22	U33	U12	U13	U23
I1	0.02413 (8)	0.02921 (8)	0.02755 (8)	0.00073 (5)	0.00534 (5)	0.00927 (5)
S1	0.0237 (2)	0.0259 (2)	0.0223 (2)	0.00194 (18)	−0.00089 (18)	0.00417 (18)
O1	0.0210 (7)	0.0248 (7)	0.0242 (7)	−0.0001 (5)	0.0038 (5)	0.0039 (5)
O2	0.0221 (7)	0.0389 (9)	0.0338 (8)	0.0025 (6)	0.0019 (6)	0.0022 (6)
O3	0.0392 (9)	0.0337 (8)	0.0312 (8)	0.0025 (7)	−0.0044 (7)	0.0138 (6)
C1	0.0218 (9)	0.0223 (9)	0.0211 (9)	0.0025 (7)	0.0017 (7)	0.0024 (7)
C2	0.0201 (9)	0.0189 (8)	0.0227 (9)	0.0030 (7)	0.0030 (7)	0.0020 (7)
C3	0.0197 (9)	0.0227 (9)	0.0256 (9)	−0.0006 (7)	0.0022 (7)	0.0024 (7)
C4	0.0226 (9)	0.0216 (9)	0.0254 (9)	0.0019 (7)	0.0064 (7)	0.0054 (7)
C5	0.0224 (9)	0.0237 (9)	0.0224 (9)	0.0041 (7)	0.0017 (7)	0.0046 (7)
C6	0.0204 (9)	0.0183 (8)	0.0257 (9)	0.0030 (7)	0.0009 (7)	0.0010 (7)
C7	0.0206 (9)	0.0189 (8)	0.0239 (9)	0.0021 (7)	0.0056 (7)	0.0039 (7)
C8	0.0249 (9)	0.0223 (9)	0.0230 (9)	0.0046 (7)	0.0025 (7)	0.0036 (7)
C9	0.0202 (9)	0.0300 (10)	0.0302 (10)	−0.0015 (8)	−0.0014 (8)	0.0054 (8)
C10	0.0329 (11)	0.0346 (11)	0.0277 (10)	0.0014 (9)	0.0071 (9)	0.0100 (8)
C11	0.0289 (10)	0.0245 (9)	0.0203 (9)	−0.0009 (8)	0.0019 (8)	0.0036 (7)
C12	0.0302 (11)	0.0368 (12)	0.0294 (11)	−0.0073 (9)	0.0045 (9)	−0.0034 (9)
C13	0.0499 (16)	0.0352 (13)	0.0436 (14)	−0.0134 (11)	0.0089 (12)	−0.0092 (10)
C14	0.0479 (15)	0.0363 (13)	0.0398 (13)	−0.0014 (11)	0.0066 (11)	−0.0106 (10)
C15	0.0369 (13)	0.0331 (12)	0.0353 (12)	0.0053 (9)	0.0057 (10)	−0.0009 (9)
C16	0.0304 (11)	0.0312 (11)	0.0286 (10)	0.0011 (8)	0.0068 (9)	0.0047 (8)

I1—C4	2.097 (2)	C9—H9C	0.9800
I1—O2i	3.2688 (17)	C10—H10A	0.9800
S1—O2	1.4401 (17)	C10—H10B	0.9800
S1—O3	1.4403 (16)	C10—H10C	0.9800
S1—C1	1.742 (2)	C11—C16	1.522 (3)
S1—C11	1.790 (2)	C11—C12	1.530 (3)
O1—C8	1.365 (2)	C11—H11	1.0000
O1—C7	1.376 (2)	C12—C13	1.527 (3)
C1—C8	1.361 (3)	C12—H12A	0.9900
C1—C2	1.446 (3)	C12—H12B	0.9900
C2—C3	1.386 (3)	C13—C14	1.510 (4)
C2—C7	1.389 (3)	C13—H13A	0.9900
C3—C4	1.390 (3)	C13—H13B	0.9900
C3—H3	0.9500	C14—C15	1.528 (3)
C4—C5	1.398 (3)	C14—H14A	0.9900
C5—C6	1.380 (3)	C14—H14B	0.9900
C5—H5	0.9500	C15—C16	1.529 (3)
C6—C7	1.386 (3)	C15—H15A	0.9900
C6—C9	1.503 (3)	C15—H15B	0.9900
C8—C10	1.472 (3)	C16—H16A	0.9900
C9—H9A	0.9800	C16—H16B	0.9900
C9—H9B	0.9800
C4—I1—O2i	168.48 (6)	H10A—C10—H10B	109.5
O2—S1—O3	118.27 (10)	C8—C10—H10C	109.5
O2—S1—C1	107.00 (9)	H10A—C10—H10C	109.5
O3—S1—C1	109.53 (10)	H10B—C10—H10C	109.5
O2—S1—C11	107.41 (10)	C16—C11—C12	111.79 (17)
O3—S1—C11	109.40 (10)	C16—C11—S1	111.94 (14)
C1—S1—C11	104.32 (9)	C12—C11—S1	109.81 (15)
C8—O1—C7	107.13 (15)	C16—C11—H11	107.7
C8—C1—C2	107.46 (17)	C12—C11—H11	107.7
C8—C1—S1	127.49 (16)	S1—C11—H11	107.7
C2—C1—S1	124.98 (15)	C13—C12—C11	109.4 (2)
C3—C2—C7	119.59 (18)	C13—C12—H12A	109.8
C3—C2—C1	135.79 (18)	C11—C12—H12A	109.8
C7—C2—C1	104.61 (17)	C13—C12—H12B	109.8
C2—C3—C4	116.60 (18)	C11—C12—H12B	109.8
C2—C3—H3	121.7	H12A—C12—H12B	108.2
C4—C3—H3	121.7	C14—C13—C12	111.6 (2)
C3—C4—C5	122.42 (19)	C14—C13—H13A	109.3
C3—C4—I1	118.52 (14)	C12—C13—H13A	109.3
C5—C4—I1	119.05 (14)	C14—C13—H13B	109.3
C6—C5—C4	121.71 (18)	C12—C13—H13B	109.3
C6—C5—H5	119.1	H13A—C13—H13B	108.0
C4—C5—H5	119.1	C13—C14—C15	111.3 (2)
C5—C6—C7	114.71 (17)	C13—C14—H14A	109.4
C5—C6—C9	123.24 (19)	C15—C14—H14A	109.4
C7—C6—C9	122.03 (19)	C13—C14—H14B	109.4
O1—C7—C6	124.57 (17)	C15—C14—H14B	109.4
O1—C7—C2	110.47 (16)	H14A—C14—H14B	108.0
C6—C7—C2	124.95 (19)	C14—C15—C16	111.3 (2)
C1—C8—O1	110.33 (17)	C14—C15—H15A	109.4
C1—C8—C10	134.78 (19)	C16—C15—H15A	109.4
O1—C8—C10	114.89 (18)	C14—C15—H15B	109.4
C6—C9—H9A	109.5	C16—C15—H15B	109.4
C6—C9—H9B	109.5	H15A—C15—H15B	108.0
H9A—C9—H9B	109.5	C11—C16—C15	110.27 (19)
C6—C9—H9C	109.5	C11—C16—H16A	109.6
H9A—C9—H9C	109.5	C15—C16—H16A	109.6
H9B—C9—H9C	109.5	C11—C16—H16B	109.6
C8—C10—H10A	109.5	C15—C16—H16B	109.6
C8—C10—H10B	109.5	H16A—C16—H16B	108.1
O2—S1—C1—C8	−150.57 (18)	C9—C6—C7—C2	177.36 (18)
O3—S1—C1—C8	−21.2 (2)	C3—C2—C7—O1	179.81 (16)
C11—S1—C1—C8	95.78 (19)	C1—C2—C7—O1	0.2 (2)
O2—S1—C1—C2	32.94 (19)	C3—C2—C7—C6	1.2 (3)
O3—S1—C1—C2	162.28 (16)	C1—C2—C7—C6	−178.46 (18)
C11—S1—C1—C2	−80.70 (18)	C2—C1—C8—O1	−0.2 (2)
C8—C1—C2—C3	−179.5 (2)	S1—C1—C8—O1	−177.21 (14)
S1—C1—C2—C3	−2.4 (3)	C2—C1—C8—C10	179.9 (2)
C8—C1—C2—C7	0.0 (2)	S1—C1—C8—C10	2.9 (4)
S1—C1—C2—C7	177.11 (14)	C7—O1—C8—C1	0.3 (2)
C7—C2—C3—C4	−0.5 (3)	C7—O1—C8—C10	−179.77 (16)
C1—C2—C3—C4	179.0 (2)	O2—S1—C11—C16	172.45 (14)
C2—C3—C4—C5	0.0 (3)	O3—S1—C11—C16	42.91 (17)
C2—C3—C4—I1	−178.70 (13)	C1—S1—C11—C16	−74.20 (16)
O2i—I1—C4—C3	54.4 (4)	O2—S1—C11—C12	47.67 (17)
O2i—I1—C4—C5	−124.3 (3)	O3—S1—C11—C12	−81.87 (17)
C3—C4—C5—C6	0.0 (3)	C1—S1—C11—C12	161.02 (15)
I1—C4—C5—C6	178.69 (14)	C16—C11—C12—C13	57.2 (3)
C4—C5—C6—C7	0.5 (3)	S1—C11—C12—C13	−177.91 (17)
C4—C5—C6—C9	−177.95 (18)	C11—C12—C13—C14	−56.7 (3)
C8—O1—C7—C6	178.33 (18)	C12—C13—C14—C15	56.3 (3)
C8—O1—C7—C2	−0.3 (2)	C13—C14—C15—C16	−55.2 (3)
C5—C6—C7—O1	−179.56 (17)	C12—C11—C16—C15	−56.8 (2)
C9—C6—C7—O1	−1.1 (3)	S1—C11—C16—C15	179.57 (15)
C5—C6—C7—C2	−1.1 (3)	C14—C15—C16—C11	55.0 (3)