5-Iodo-7-methyl-2-(4-methyl-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

In the title compound, C17H15IO2S, the dihedral angle between the benzofuran group (r.m.s. deviation = 0.009 Å) and the 4-methylbenzene ring is 12.69 (5)°. In the crystal, mol-ecules are linked via pairs of I⋯O [I⋯O = 3.164 (1) Å, C-I⋯O = 166.63 (5)°] contacts into inversion-related dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2010 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H15IO2S

M = 410.25

Triclinic,

a = 7.6816 (3) Å

b = 9.6478 (4) Å

c = 11.3738 (4) Å

α = 75.409 (2)°

β = 84.062 (2)°

γ = 71.684 (2)°

V = 774.14 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.20 mm−1

T = 173 K

0.25 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.607, T max = 0.652

14337 measured reflections

3858 independent reflections

3637 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.044

S = 1.09

3858 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.41 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/S1600536814000865/pk2514sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000865/pk2514Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000865/pk2514Isup3.cml

CCDC reference:

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

C17H15IO2S	Z = 2
Mr = 410.25	F(000) = 404
Triclinic, P1	Dx = 1.760 Mg m−3
Hall symbol: -P 1	Melting point = 483–484 K
a = 7.6816 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6478 (4) Å	Cell parameters from 9908 reflections
c = 11.3738 (4) Å	θ = 2.6–28.4°
α = 75.409 (2)°	µ = 2.20 mm−1
β = 84.062 (2)°	T = 173 K
γ = 71.684 (2)°	Block, colourless
V = 774.14 (5) Å3	0.25 × 0.25 × 0.21 mm

Bruker SMART APEXII CCD diffractometer	3858 independent reflections
Radiation source: rotating anode	3637 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.019
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.607, Tmax = 0.652	l = −15→15
14337 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)] = 0.017	Hydrogen site location: difference Fourier map
wR(F2) = 0.044	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0222P)2 + 0.2874P] where P = (Fo2 + 2Fc2)/3
3858 reflections	(Δ/σ)max = 0.002
193 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.41 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	−0.019314 (14)	0.745216 (11)	−0.052801 (9)	0.02619 (4)
S1	0.34602 (7)	0.20502 (4)	0.38345 (4)	0.03019 (9)
O1	0.19544 (15)	0.59238 (12)	0.48325 (10)	0.0235 (2)
O2	0.2168 (2)	0.19491 (16)	0.29934 (14)	0.0444 (4)
C1	0.2754 (2)	0.39157 (17)	0.40042 (15)	0.0230 (3)
C2	0.1875 (2)	0.52209 (17)	0.30798 (14)	0.0216 (3)
C4	0.0549 (2)	0.69626 (18)	0.12932 (15)	0.0228 (3)
C5	0.0068 (2)	0.81375 (18)	0.18956 (15)	0.0247 (3)
H5	−0.0561	0.9125	0.1469	0.030*
C6	0.0492 (2)	0.78875 (18)	0.31048 (15)	0.0242 (3)
C7	0.1397 (2)	0.64097 (17)	0.36481 (14)	0.0217 (3)
C8	0.2778 (2)	0.43936 (17)	0.50377 (14)	0.0221 (3)
C9	0.0053 (3)	0.9109 (2)	0.37826 (18)	0.0347 (4)
H9A	−0.1026	0.9073	0.4317	0.052*
H9B	−0.0203	1.0086	0.3202	0.052*
H9C	0.1100	0.8965	0.4272	0.052*
C10	0.3492 (2)	0.36861 (18)	0.62510 (14)	0.0226 (3)
C11	0.4716 (2)	0.22337 (19)	0.65298 (15)	0.0273 (3)
H11	0.5087	0.1680	0.5918	0.033*
C12	0.5393 (2)	0.1594 (2)	0.76906 (16)	0.0282 (3)
H12	0.6204	0.0599	0.7867	0.034*
C13	0.4905 (2)	0.2385 (2)	0.85977 (15)	0.0258 (3)
C14	0.3695 (2)	0.3839 (2)	0.83131 (16)	0.0284 (3)
H14	0.3353	0.4401	0.8921	0.034*
C15	0.2985 (2)	0.44779 (19)	0.71653 (15)	0.0266 (3)
H15	0.2147	0.5462	0.6998	0.032*
C3	0.1452 (2)	0.54937 (18)	0.18552 (15)	0.0237 (3)
H3	0.1771	0.4711	0.1434	0.028*
C16	0.5645 (3)	0.1710 (2)	0.98538 (16)	0.0323 (4)
H16A	0.4648	0.1543	1.0428	0.049*
H16B	0.6178	0.2396	1.0090	0.049*
H16C	0.6592	0.0750	0.9863	0.049*
C17	0.5538 (3)	0.2117 (3)	0.2978 (2)	0.0455 (5)
H17A	0.6066	0.1191	0.2693	0.068*
H17B	0.6414	0.2219	0.3495	0.068*
H17C	0.5270	0.2980	0.2279	0.068*

	U11	U22	U33	U12	U13	U23
I1	0.03146 (6)	0.02535 (6)	0.02107 (6)	−0.00844 (4)	−0.00869 (4)	−0.00105 (4)
S1	0.0457 (2)	0.01849 (18)	0.0264 (2)	−0.00770 (17)	−0.01246 (18)	−0.00318 (16)
O1	0.0287 (6)	0.0218 (5)	0.0188 (5)	−0.0053 (4)	−0.0034 (4)	−0.0041 (4)
O2	0.0641 (9)	0.0315 (7)	0.0452 (8)	−0.0174 (7)	−0.0248 (7)	−0.0091 (6)
C1	0.0282 (7)	0.0197 (7)	0.0211 (7)	−0.0075 (6)	−0.0051 (6)	−0.0023 (6)
C2	0.0237 (7)	0.0200 (7)	0.0211 (7)	−0.0076 (6)	−0.0041 (6)	−0.0021 (6)
C4	0.0249 (7)	0.0245 (7)	0.0196 (7)	−0.0097 (6)	−0.0058 (6)	−0.0013 (6)
C5	0.0260 (7)	0.0207 (7)	0.0246 (8)	−0.0053 (6)	−0.0059 (6)	−0.0003 (6)
C6	0.0253 (7)	0.0216 (7)	0.0246 (8)	−0.0053 (6)	−0.0021 (6)	−0.0052 (6)
C7	0.0235 (7)	0.0232 (7)	0.0184 (7)	−0.0071 (6)	−0.0035 (6)	−0.0034 (6)
C8	0.0233 (7)	0.0213 (7)	0.0213 (7)	−0.0070 (6)	−0.0020 (6)	−0.0032 (6)
C9	0.0448 (10)	0.0246 (8)	0.0299 (9)	0.0004 (7)	−0.0061 (8)	−0.0096 (7)
C10	0.0246 (7)	0.0253 (7)	0.0193 (7)	−0.0106 (6)	−0.0024 (6)	−0.0027 (6)
C11	0.0322 (8)	0.0274 (8)	0.0211 (8)	−0.0055 (7)	−0.0045 (7)	−0.0064 (7)
C12	0.0294 (8)	0.0272 (8)	0.0243 (8)	−0.0053 (6)	−0.0058 (7)	−0.0012 (7)
C13	0.0249 (7)	0.0334 (8)	0.0198 (7)	−0.0129 (7)	−0.0040 (6)	−0.0007 (7)
C14	0.0331 (8)	0.0330 (9)	0.0210 (8)	−0.0109 (7)	−0.0013 (7)	−0.0080 (7)
C15	0.0294 (8)	0.0263 (8)	0.0233 (8)	−0.0072 (6)	−0.0024 (6)	−0.0054 (7)
C3	0.0280 (8)	0.0229 (7)	0.0224 (8)	−0.0095 (6)	−0.0048 (6)	−0.0052 (6)
C16	0.0316 (9)	0.0440 (10)	0.0211 (8)	−0.0130 (8)	−0.0071 (7)	−0.0023 (7)
C17	0.0470 (12)	0.0409 (11)	0.0454 (12)	−0.0025 (9)	0.0023 (10)	−0.0194 (10)

I1—C4	2.1025 (16)	C9—H9C	0.9800
S1—O2	1.4879 (14)	C10—C15	1.395 (2)
I1—O2i	3.1642 (14)	C10—C11	1.399 (2)
S1—C1	1.7637 (16)	C11—C12	1.387 (2)
S1—C17	1.792 (2)	C11—H11	0.9500
O1—C7	1.3759 (18)	C12—C13	1.387 (2)
O1—C8	1.3799 (18)	C12—H12	0.9500
C1—C8	1.370 (2)	C13—C14	1.396 (3)
C1—C2	1.447 (2)	C13—C16	1.502 (2)
C2—C7	1.389 (2)	C14—C15	1.383 (2)
C2—C3	1.403 (2)	C14—H14	0.9500
C4—C3	1.384 (2)	C15—H15	0.9500
C4—C5	1.402 (2)	C3—H3	0.9500
C5—C6	1.390 (2)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.386 (2)	C16—H16C	0.9800
C6—C9	1.500 (2)	C17—H17A	0.9800
C8—C10	1.455 (2)	C17—H17B	0.9800
C9—H9A	0.9800	C17—H17C	0.9800
C9—H9B	0.9800
C4—I1—O2i	166.63 (5)	C15—C10—C8	119.69 (15)
O2—S1—C1	107.08 (8)	C11—C10—C8	121.93 (14)
O2—S1—C17	106.95 (10)	C12—C11—C10	120.71 (15)
C1—S1—C17	97.23 (9)	C12—C11—H11	119.6
C7—O1—C8	107.01 (12)	C10—C11—H11	119.6
C8—C1—C2	107.37 (14)	C11—C12—C13	120.98 (16)
C8—C1—S1	127.41 (13)	C11—C12—H12	119.5
C2—C1—S1	125.00 (12)	C13—C12—H12	119.5
C7—C2—C3	119.35 (14)	C12—C13—C14	118.12 (15)
C7—C2—C1	105.00 (14)	C12—C13—C16	121.45 (16)
C3—C2—C1	135.65 (14)	C14—C13—C16	120.44 (15)
C3—C4—C5	122.76 (15)	C15—C14—C13	121.40 (16)
C3—C4—I1	118.82 (11)	C15—C14—H14	119.3
C5—C4—I1	118.40 (12)	C13—C14—H14	119.3
C6—C5—C4	121.36 (15)	C14—C15—C10	120.41 (16)
C6—C5—H5	119.3	C14—C15—H15	119.8
C4—C5—H5	119.3	C10—C15—H15	119.8
C7—C6—C5	114.86 (14)	C4—C3—C2	116.55 (14)
C7—C6—C9	121.60 (15)	C4—C3—H3	121.7
C5—C6—C9	123.53 (15)	C2—C3—H3	121.7
O1—C7—C6	124.21 (14)	C13—C16—H16A	109.5
O1—C7—C2	110.68 (13)	C13—C16—H16B	109.5
C6—C7—C2	125.11 (15)	H16A—C16—H16B	109.5
C1—C8—O1	109.92 (14)	C13—C16—H16C	109.5
C1—C8—C10	135.43 (15)	H16A—C16—H16C	109.5
O1—C8—C10	114.62 (13)	H16B—C16—H16C	109.5
C6—C9—H9A	109.5	S1—C17—H17A	109.5
C6—C9—H9B	109.5	S1—C17—H17B	109.5
H9A—C9—H9B	109.5	H17A—C17—H17B	109.5
C6—C9—H9C	109.5	S1—C17—H17C	109.5
H9A—C9—H9C	109.5	H17A—C17—H17C	109.5
H9B—C9—H9C	109.5	H17B—C17—H17C	109.5
C15—C10—C11	118.36 (15)
O2—S1—C1—C8	142.69 (15)	S1—C1—C8—O1	−174.32 (11)
C17—S1—C1—C8	−107.04 (17)	C2—C1—C8—C10	−177.62 (17)
O2—S1—C1—C2	−31.25 (17)	S1—C1—C8—C10	7.6 (3)
C17—S1—C1—C2	79.02 (16)	C7—O1—C8—C1	0.29 (17)
C8—C1—C2—C7	−1.04 (17)	C7—O1—C8—C10	178.82 (13)
S1—C1—C2—C7	173.92 (12)	C1—C8—C10—C15	−168.65 (18)
C8—C1—C2—C3	179.06 (17)	O1—C8—C10—C15	13.3 (2)
S1—C1—C2—C3	−6.0 (3)	C1—C8—C10—C11	12.8 (3)
C3—C4—C5—C6	0.5 (3)	O1—C8—C10—C11	−165.23 (14)
I1—C4—C5—C6	179.04 (12)	C15—C10—C11—C12	0.6 (2)
C4—C5—C6—C7	−0.5 (2)	C8—C10—C11—C12	179.16 (15)
C4—C5—C6—C9	178.40 (17)	C10—C11—C12—C13	−1.2 (3)
C8—O1—C7—C6	179.35 (15)	C11—C12—C13—C14	0.7 (2)
C8—O1—C7—C2	−0.99 (17)	C11—C12—C13—C16	−179.36 (16)
C5—C6—C7—O1	179.41 (14)	C12—C13—C14—C15	0.5 (2)
C9—C6—C7—O1	0.5 (3)	C16—C13—C14—C15	−179.46 (16)
C5—C6—C7—C2	−0.2 (2)	C13—C14—C15—C10	−1.1 (3)
C9—C6—C7—C2	−179.08 (16)	C11—C10—C15—C14	0.6 (2)
C3—C2—C7—O1	−178.83 (13)	C8—C10—C15—C14	−178.03 (15)
C1—C2—C7—O1	1.25 (17)	C5—C4—C3—C2	0.1 (2)
C3—C2—C7—C6	0.8 (2)	I1—C4—C3—C2	−178.41 (11)
C1—C2—C7—C6	−179.09 (15)	C7—C2—C3—C4	−0.7 (2)
C2—C1—C8—O1	0.47 (18)	C1—C2—C3—C4	179.15 (17)