Crystal structure of 5-iodo-2-methyl-3-[(4-methyl-phenyl)-sulfon-yl]-1-benzo-furan.

In the title compound, C16H13IO3S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (2) Å] and the 4-methyl-phenyl ring is 70.35 (5)°. In the crystal, mol-ecules are linked by pairs of π-π inter-actions between the furan and benzene rings, with centroid-centroid distances of 3.667 (3) and 3.701 (3) Å. The mol-ecules stack along the a-axis direction. In addition, pairs of C-H⋯O hydrogen bonds between inversion-related dimers [which generate R 2 (2)(10) loops] and a short I⋯I [3.7534 (3) Å] contact are observed.

Related literature

For a related structure and background to benzo­furan derivatives, see: Choi & Lee (2014 ▶). For further synthetic details, see: Choi et al. (1999 ▶).

Experimental

Crystal data

C16H13IO3S

M = 412.22

Triclinic,

a = 7.2161 (1) Å

b = 10.5267 (2) Å

c = 11.3442 (2) Å

α = 111.540 (1)°

β = 90.882 (1)°

γ = 108.760 (1)°

V = 750.19 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.28 mm−1

T = 173 K

0.45 × 0.37 × 0.33 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.427, T max = 0.520

13690 measured reflections

3730 independent reflections

3508 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.059

S = 1.09

3730 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.82 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814018510/hb7273sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018510/hb7273Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018510/hb7273Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018510/hb7273fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

x y z x y z x y z x y z . DOI: 10.1107/S1600536814018510/hb7273fig2.tif

A view of the C—H⋯O, π–π and I⋯I inter­actions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) − x + 1, − y + 1, − z + 2; (ii) − x + 1, − y, − z; (iii) − x, − y, − z + 1; (iv) − x + 1, − y, − z + 1.]

CCDC reference: 1019339

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H13IO3S	Z = 2
Mr = 412.22	F(000) = 404
Triclinic, P1	Dx = 1.825 Mg m−3
Hall symbol: -P 1	Melting point = 462–461 K
a = 7.2161 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5267 (2) Å	Cell parameters from 9550 reflections
c = 11.3442 (2) Å	θ = 3.0–28.4°
α = 111.540 (1)°	µ = 2.28 mm−1
β = 90.882 (1)°	T = 173 K
γ = 108.760 (1)°	Block, colourless
V = 750.19 (2) Å3	0.45 × 0.37 × 0.33 mm

Bruker SMART APEXII CCD diffractometer	3730 independent reflections
Radiation source: rotating anode	3508 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.0°
φ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→12
Tmin = 0.427, Tmax = 0.520	l = −15→15
13690 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) = 0.059	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0251P)2 + 0.4508P] where P = (Fo2 + 2Fc2)/3
3730 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.82 e Å−3

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.23 (s, 1H), 7.87 (d, J = 8.56 Hz, 2H), 7.58 (dd, J = 8.56 and 1.72 Hz, 1H), 7.32 (d, J = 8.20 Hz, 2H), 7.17 (d, J = 8.56 Hz, 1H), 2.78 (s, 3H), 2.40 (s, 3H).

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	0.34881 (2)	0.005191 (17)	0.133697 (13)	0.03924 (6)
S1	0.51630 (7)	0.39711 (5)	0.72563 (4)	0.02485 (10)
O1	0.1860 (2)	−0.00618 (16)	0.66250 (15)	0.0303 (3)
O2	0.6298 (2)	0.41551 (16)	0.62596 (13)	0.0302 (3)
O3	0.6169 (2)	0.43950 (18)	0.85197 (14)	0.0346 (3)
C1	0.3716 (3)	0.2132 (2)	0.66867 (18)	0.0245 (4)
C2	0.3274 (3)	0.1121 (2)	0.53672 (18)	0.0236 (4)
C3	0.3694 (3)	0.1210 (2)	0.41971 (19)	0.0257 (4)
H3	0.4451	0.2108	0.4148	0.031*
C4	0.2959 (3)	−0.0065 (2)	0.31154 (19)	0.0283 (4)
C5	0.1880 (3)	−0.1412 (2)	0.3154 (2)	0.0329 (4)
H5	0.1444	−0.2267	0.2386	0.040*
C6	0.1449 (3)	−0.1498 (2)	0.4313 (2)	0.0326 (4)
H6	0.0707	−0.2398	0.4364	0.039*
C7	0.2144 (3)	−0.0220 (2)	0.5385 (2)	0.0268 (4)
C8	0.2817 (3)	0.1378 (2)	0.7397 (2)	0.0281 (4)
C9	0.2619 (3)	0.1795 (3)	0.8770 (2)	0.0365 (5)
H9A	0.3626	0.2751	0.9271	0.055*
H9B	0.2802	0.1066	0.9058	0.055*
H9C	0.1299	0.1844	0.8893	0.055*
C10	0.3497 (3)	0.4906 (2)	0.73988 (18)	0.0248 (4)
C11	0.3006 (3)	0.5246 (2)	0.63922 (19)	0.0288 (4)
H11	0.3530	0.4950	0.5615	0.035*
C12	0.1741 (3)	0.6022 (2)	0.6538 (2)	0.0328 (4)
H12	0.1422	0.6274	0.5858	0.039*
C13	0.0926 (3)	0.6441 (2)	0.7656 (2)	0.0309 (4)
C14	0.1398 (3)	0.6056 (2)	0.8638 (2)	0.0345 (5)
H14	0.0825	0.6315	0.9399	0.041*
C15	0.2688 (3)	0.5302 (2)	0.85277 (19)	0.0317 (4)
H15	0.3016	0.5059	0.9211	0.038*
C16	−0.0386 (4)	0.7339 (2)	0.7832 (3)	0.0412 (5)
H16A	0.0429	0.8378	0.8215	0.062*
H16B	−0.1335	0.7112	0.8399	0.062*
H16C	−0.1104	0.7110	0.6998	0.062*

	U11	U22	U33	U12	U13	U23
I1	0.04516 (10)	0.04799 (10)	0.02485 (8)	0.02137 (7)	0.00481 (6)	0.01037 (6)
S1	0.0240 (2)	0.0273 (2)	0.0206 (2)	0.00442 (17)	0.00161 (17)	0.01065 (18)
O1	0.0292 (7)	0.0299 (7)	0.0393 (8)	0.0103 (6)	0.0085 (6)	0.0220 (6)
O2	0.0286 (7)	0.0306 (7)	0.0267 (7)	0.0034 (6)	0.0067 (6)	0.0122 (6)
O3	0.0315 (7)	0.0426 (8)	0.0248 (7)	0.0068 (6)	−0.0035 (6)	0.0135 (6)
C1	0.0223 (8)	0.0273 (9)	0.0269 (9)	0.0090 (7)	0.0047 (7)	0.0137 (8)
C2	0.0197 (8)	0.0248 (9)	0.0292 (9)	0.0091 (7)	0.0029 (7)	0.0128 (7)
C3	0.0245 (9)	0.0259 (9)	0.0277 (9)	0.0085 (7)	0.0032 (7)	0.0119 (8)
C4	0.0269 (9)	0.0314 (10)	0.0281 (10)	0.0144 (8)	0.0017 (7)	0.0100 (8)
C5	0.0312 (10)	0.0265 (10)	0.0369 (11)	0.0121 (8)	−0.0046 (8)	0.0065 (8)
C6	0.0278 (10)	0.0237 (9)	0.0472 (12)	0.0083 (8)	0.0008 (9)	0.0158 (9)
C7	0.0224 (8)	0.0287 (9)	0.0355 (10)	0.0106 (7)	0.0043 (7)	0.0182 (8)
C8	0.0256 (9)	0.0328 (10)	0.0335 (10)	0.0126 (8)	0.0057 (8)	0.0192 (8)
C9	0.0394 (12)	0.0470 (13)	0.0352 (11)	0.0175 (10)	0.0129 (9)	0.0269 (10)
C10	0.0285 (9)	0.0209 (8)	0.0216 (8)	0.0046 (7)	0.0016 (7)	0.0084 (7)
C11	0.0320 (10)	0.0302 (10)	0.0222 (9)	0.0064 (8)	0.0042 (7)	0.0120 (8)
C12	0.0351 (11)	0.0312 (10)	0.0325 (11)	0.0065 (8)	0.0004 (8)	0.0176 (9)
C13	0.0280 (9)	0.0198 (9)	0.0388 (11)	0.0024 (7)	0.0036 (8)	0.0103 (8)
C14	0.0426 (12)	0.0287 (10)	0.0300 (10)	0.0121 (9)	0.0111 (9)	0.0094 (8)
C15	0.0427 (11)	0.0307 (10)	0.0212 (9)	0.0113 (9)	0.0047 (8)	0.0111 (8)
C16	0.0402 (12)	0.0277 (11)	0.0558 (15)	0.0123 (9)	0.0077 (11)	0.0161 (10)

I1—C4	2.099 (2)	C8—C9	1.478 (3)
I1—I1i	3.7534 (3)	C9—H9A	0.9800
S1—O3	1.4389 (14)	C9—H9B	0.9800
S1—O2	1.4400 (14)	C9—H9C	0.9800
S1—C1	1.737 (2)	C10—C11	1.388 (3)
S1—C10	1.758 (2)	C10—C15	1.394 (3)
O1—C8	1.369 (3)	C11—C12	1.383 (3)
O1—C7	1.381 (3)	C11—H11	0.9500
C1—C8	1.362 (3)	C12—C13	1.388 (3)
C1—C2	1.439 (3)	C12—H12	0.9500
C2—C7	1.393 (3)	C13—C14	1.389 (3)
C2—C3	1.396 (3)	C13—C16	1.507 (3)
C3—C4	1.379 (3)	C14—C15	1.384 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.398 (3)	C15—H15	0.9500
C5—C6	1.384 (3)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.374 (3)	C16—H16C	0.9800
C6—H6	0.9500
C4—I1—I1i	152.81 (5)	O1—C8—C9	115.80 (17)
O3—S1—O2	119.63 (9)	C8—C9—H9A	109.5
O3—S1—C1	108.45 (10)	C8—C9—H9B	109.5
O2—S1—C1	106.07 (9)	H9A—C9—H9B	109.5
O3—S1—C10	107.93 (10)	C8—C9—H9C	109.5
O2—S1—C10	108.10 (9)	H9A—C9—H9C	109.5
C1—S1—C10	105.86 (9)	H9B—C9—H9C	109.5
C8—O1—C7	107.15 (15)	C11—C10—C15	120.7 (2)
C8—C1—C2	107.56 (17)	C11—C10—S1	119.87 (16)
C8—C1—S1	126.69 (16)	C15—C10—S1	119.40 (16)
C2—C1—S1	125.74 (14)	C12—C11—C10	118.98 (19)
C7—C2—C3	119.25 (18)	C12—C11—H11	120.5
C7—C2—C1	105.06 (17)	C10—C11—H11	120.5
C3—C2—C1	135.69 (17)	C11—C12—C13	121.5 (2)
C4—C3—C2	116.96 (18)	C11—C12—H12	119.3
C4—C3—H3	121.5	C13—C12—H12	119.3
C2—C3—H3	121.5	C12—C13—C14	118.5 (2)
C3—C4—C5	123.1 (2)	C12—C13—C16	121.3 (2)
C3—C4—I1	117.72 (15)	C14—C13—C16	120.1 (2)
C5—C4—I1	119.19 (15)	C15—C14—C13	121.3 (2)
C6—C5—C4	119.9 (2)	C15—C14—H14	119.4
C6—C5—H5	120.0	C13—C14—H14	119.4
C4—C5—H5	120.0	C14—C15—C10	118.99 (19)
C7—C6—C5	116.79 (19)	C14—C15—H15	120.5
C7—C6—H6	121.6	C10—C15—H15	120.5
C5—C6—H6	121.6	C13—C16—H16A	109.5
C6—C7—O1	126.11 (18)	C13—C16—H16B	109.5
C6—C7—C2	123.91 (19)	H16A—C16—H16B	109.5
O1—C7—C2	109.97 (17)	C13—C16—H16C	109.5
C1—C8—O1	110.23 (18)	H16A—C16—H16C	109.5
C1—C8—C9	133.9 (2)	H16B—C16—H16C	109.5
O3—S1—C1—C8	31.6 (2)	C3—C2—C7—O1	−178.42 (16)
O2—S1—C1—C8	161.28 (18)	C1—C2—C7—O1	1.1 (2)
C10—S1—C1—C8	−84.0 (2)	C2—C1—C8—O1	1.4 (2)
O3—S1—C1—C2	−147.56 (17)	S1—C1—C8—O1	−177.87 (14)
O2—S1—C1—C2	−17.9 (2)	C2—C1—C8—C9	−176.3 (2)
C10—S1—C1—C2	96.83 (18)	S1—C1—C8—C9	4.4 (4)
C8—C1—C2—C7	−1.5 (2)	C7—O1—C8—C1	−0.7 (2)
S1—C1—C2—C7	177.78 (15)	C7—O1—C8—C9	177.42 (17)
C8—C1—C2—C3	177.9 (2)	O3—S1—C10—C11	151.02 (16)
S1—C1—C2—C3	−2.8 (3)	O2—S1—C10—C11	20.28 (18)
C7—C2—C3—C4	−0.5 (3)	C1—S1—C10—C11	−93.02 (17)
C1—C2—C3—C4	−179.8 (2)	O3—S1—C10—C15	−28.79 (18)
C2—C3—C4—C5	−1.6 (3)	O2—S1—C10—C15	−159.52 (15)
C2—C3—C4—I1	178.02 (14)	C1—S1—C10—C15	87.17 (17)
I1i—I1—C4—C3	89.06 (19)	C15—C10—C11—C12	1.8 (3)
I1i—I1—C4—C5	−91.27 (19)	S1—C10—C11—C12	−178.00 (15)
C3—C4—C5—C6	2.3 (3)	C10—C11—C12—C13	−1.3 (3)
I1—C4—C5—C6	−177.38 (15)	C11—C12—C13—C14	−0.4 (3)
C4—C5—C6—C7	−0.6 (3)	C11—C12—C13—C16	177.49 (19)
C5—C6—C7—O1	179.13 (19)	C12—C13—C14—C15	1.5 (3)
C5—C6—C7—C2	−1.5 (3)	C16—C13—C14—C15	−176.3 (2)
C8—O1—C7—C6	179.2 (2)	C13—C14—C15—C10	−1.0 (3)
C8—O1—C7—C2	−0.3 (2)	C11—C10—C15—C14	−0.7 (3)
C3—C2—C7—C6	2.1 (3)	S1—C10—C15—C14	179.13 (16)
C1—C2—C7—C6	−178.35 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3ii	0.95	2.44	3.311 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O3i	0.95	2.44	3.311 (2)	153

Symmetry code: (i) .