3-(4-Fluoro-phenyl-sulfin-yl)-5-iodo-2,7-dimethyl-1-benzofuran.

In the title compound, C(16)H(12)FlO(2)S, the 4-fluoro-phenyl ring makes a dihedral angle of 80.21 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O hydrogen bonds. The crystal structure also exhibits an inter-molecular I⋯F contact [3.423 (2) Å].

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 our previous structural studies of related 3-(4-fluoro­phenyl­sulfin­yl)-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶).

Experimental

Crystal data

C16H12FIO2S

M = 414.22

Triclinic,

a = 9.0845 (2) Å

b = 9.2761 (2) Å

c = 10.1252 (2) Å

α = 71.315 (1)°

β = 80.838 (1)°

γ = 70.485 (1)°

V = 760.53 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.25 mm−1

T = 173 K

0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.603, T max = 0.666

13286 measured reflections

3477 independent reflections

3276 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.065

S = 1.15

3477 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −1.25 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/S1600536811012591/bv2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012591/bv2179Isup2.hkl

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

C16H12FIO2S	Z = 2
Mr = 414.22	F(000) = 404
Triclinic, P1	Dx = 1.809 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0845 (2) Å	Cell parameters from 9933 reflections
b = 9.2761 (2) Å	θ = 2.4–27.5°
c = 10.1252 (2) Å	µ = 2.25 mm−1
α = 71.315 (1)°	T = 173 K
β = 80.838 (1)°	Block, colourless
γ = 70.485 (1)°	0.25 × 0.23 × 0.20 mm
V = 760.53 (3) Å3

Bruker SMART APEXII CCD diffractometer	3477 independent reflections
Radiation source: rotating anode	3276 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.033
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.1°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→11
Tmin = 0.603, Tmax = 0.666	l = −13→13
13286 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)] = 0.025	Hydrogen site location: difference Fourier map
wR(F2) = 0.065	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0297P)2 + 0.3709P] where P = (Fo2 + 2Fc2)/3
3477 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −1.25 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	0.885022 (19)	0.64773 (2)	0.817121 (15)	0.04100 (7)
S1	0.46511 (6)	0.87701 (6)	0.28833 (5)	0.02623 (11)
F1	0.91534 (19)	1.2241 (2)	0.00671 (16)	0.0487 (4)
O1	0.70380 (17)	0.42169 (18)	0.37299 (15)	0.0282 (3)
O2	0.39368 (18)	0.9370 (2)	0.41076 (16)	0.0337 (3)
C1	0.5892 (2)	0.6822 (2)	0.3520 (2)	0.0247 (4)
C2	0.6891 (2)	0.6179 (2)	0.4686 (2)	0.0242 (4)
C3	0.7247 (2)	0.6783 (3)	0.5651 (2)	0.0258 (4)
H3	0.6807	0.7873	0.5631	0.031*
C4	0.8280 (2)	0.5699 (3)	0.6641 (2)	0.0289 (4)
C5	0.8967 (2)	0.4099 (3)	0.6678 (2)	0.0302 (4)
H5	0.9687	0.3419	0.7369	0.036*
C6	0.8620 (2)	0.3475 (3)	0.5724 (2)	0.0283 (4)
C8	0.6016 (2)	0.5613 (3)	0.3001 (2)	0.0269 (4)
C7	0.7563 (2)	0.4570 (3)	0.4756 (2)	0.0255 (4)
C9	0.9340 (3)	0.1760 (3)	0.5733 (3)	0.0369 (5)
H9A	0.8521	0.1323	0.5663	0.055*
H9B	0.9865	0.1146	0.6604	0.055*
H9C	1.0105	0.1694	0.4937	0.055*
C10	0.5306 (3)	0.5520 (3)	0.1823 (3)	0.0362 (5)
H10A	0.4481	0.6521	0.1470	0.054*
H10B	0.4857	0.4632	0.2145	0.054*
H10C	0.6112	0.5344	0.1074	0.054*
C11	0.6111 (2)	0.9745 (2)	0.2075 (2)	0.0254 (4)
C12	0.6769 (3)	0.9632 (3)	0.0763 (2)	0.0313 (5)
H12	0.6505	0.8982	0.0337	0.038*
C13	0.7807 (3)	1.0468 (3)	0.0079 (2)	0.0353 (5)
H13	0.8270	1.0405	−0.0819	0.042*
C14	0.8148 (3)	1.1395 (3)	0.0736 (2)	0.0333 (5)
C15	0.7536 (3)	1.1507 (3)	0.2047 (2)	0.0328 (5)
H15	0.7828	1.2132	0.2481	0.039*
C16	0.6476 (3)	1.0676 (3)	0.2718 (2)	0.0296 (4)
H16	0.6007	1.0750	0.3612	0.036*

	U11	U22	U33	U12	U13	U23
I1	0.05179 (11)	0.04985 (12)	0.02844 (9)	−0.02072 (8)	−0.01085 (7)	−0.01101 (7)
S1	0.0251 (2)	0.0264 (2)	0.0265 (2)	−0.0037 (2)	−0.00507 (18)	−0.0092 (2)
F1	0.0549 (9)	0.0500 (9)	0.0437 (8)	−0.0300 (8)	0.0008 (7)	−0.0036 (7)
O1	0.0311 (7)	0.0245 (7)	0.0302 (7)	−0.0066 (6)	−0.0046 (6)	−0.0101 (6)
O2	0.0319 (8)	0.0362 (9)	0.0336 (8)	−0.0068 (7)	0.0023 (6)	−0.0164 (7)
C1	0.0253 (9)	0.0243 (10)	0.0237 (9)	−0.0055 (8)	−0.0033 (7)	−0.0070 (8)
C2	0.0230 (9)	0.0262 (10)	0.0228 (9)	−0.0072 (8)	−0.0007 (7)	−0.0066 (8)
C3	0.0264 (9)	0.0276 (10)	0.0246 (9)	−0.0094 (8)	−0.0008 (7)	−0.0081 (8)
C4	0.0311 (10)	0.0363 (12)	0.0225 (9)	−0.0143 (9)	−0.0024 (8)	−0.0080 (9)
C5	0.0277 (10)	0.0325 (11)	0.0262 (10)	−0.0096 (9)	−0.0040 (8)	−0.0009 (9)
C6	0.0260 (9)	0.0261 (10)	0.0292 (10)	−0.0080 (8)	−0.0004 (8)	−0.0037 (8)
C8	0.0267 (9)	0.0278 (10)	0.0270 (10)	−0.0080 (8)	−0.0019 (7)	−0.0091 (8)
C7	0.0263 (9)	0.0257 (10)	0.0257 (9)	−0.0093 (8)	−0.0008 (7)	−0.0079 (8)
C9	0.0336 (11)	0.0255 (11)	0.0439 (13)	−0.0040 (9)	−0.0051 (9)	−0.0034 (10)
C10	0.0412 (12)	0.0362 (12)	0.0365 (12)	−0.0103 (10)	−0.0107 (9)	−0.0148 (10)
C11	0.0260 (9)	0.0222 (9)	0.0245 (9)	−0.0022 (8)	−0.0055 (7)	−0.0055 (8)
C12	0.0350 (11)	0.0338 (11)	0.0275 (10)	−0.0081 (9)	−0.0046 (8)	−0.0132 (9)
C13	0.0373 (11)	0.0436 (13)	0.0238 (10)	−0.0105 (10)	−0.0023 (8)	−0.0096 (10)
C14	0.0348 (11)	0.0284 (11)	0.0324 (11)	−0.0098 (9)	−0.0056 (9)	−0.0012 (9)
C15	0.0381 (11)	0.0257 (10)	0.0368 (12)	−0.0077 (9)	−0.0075 (9)	−0.0111 (9)
C16	0.0339 (10)	0.0270 (10)	0.0274 (10)	−0.0043 (9)	−0.0038 (8)	−0.0111 (9)

I1—C4	2.101 (2)	C6—C9	1.502 (3)
I1—F1i	3.4226 (16)	C8—C10	1.481 (3)
S1—O2	1.4874 (16)	C9—H9A	0.9800
S1—C1	1.754 (2)	C9—H9B	0.9800
S1—C11	1.797 (2)	C9—H9C	0.9800
F1—C14	1.360 (3)	C10—H10A	0.9800
O1—C8	1.374 (3)	C10—H10B	0.9800
O1—C7	1.377 (3)	C10—H10C	0.9800
C1—C8	1.349 (3)	C11—C16	1.378 (3)
C1—C2	1.450 (3)	C11—C12	1.388 (3)
C2—C7	1.394 (3)	C12—C13	1.381 (3)
C2—C3	1.395 (3)	C12—H12	0.9500
C3—C4	1.385 (3)	C13—C14	1.374 (4)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.396 (3)	C14—C15	1.378 (3)
C5—C6	1.395 (3)	C15—C16	1.391 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.387 (3)	C16—H16	0.9500
C4—I1—F1i	161.10 (6)	C6—C9—H9B	109.5
O2—S1—C1	107.49 (10)	H9A—C9—H9B	109.5
O2—S1—C11	106.55 (10)	C6—C9—H9C	109.5
C1—S1—C11	98.72 (9)	H9A—C9—H9C	109.5
C8—O1—C7	106.50 (16)	H9B—C9—H9C	109.5
C8—C1—C2	107.61 (18)	C8—C10—H10A	109.5
C8—C1—S1	123.72 (16)	C8—C10—H10B	109.5
C2—C1—S1	128.61 (16)	H10A—C10—H10B	109.5
C7—C2—C3	119.99 (19)	C8—C10—H10C	109.5
C7—C2—C1	104.33 (17)	H10A—C10—H10C	109.5
C3—C2—C1	135.67 (19)	H10B—C10—H10C	109.5
C4—C3—C2	116.1 (2)	C16—C11—C12	121.3 (2)
C4—C3—H3	122.0	C16—C11—S1	119.71 (16)
C2—C3—H3	122.0	C12—C11—S1	118.82 (17)
C3—C4—C5	123.2 (2)	C13—C12—C11	119.8 (2)
C3—C4—I1	119.05 (16)	C13—C12—H12	120.1
C5—C4—I1	117.79 (15)	C11—C12—H12	120.1
C6—C5—C4	121.5 (2)	C14—C13—C12	118.0 (2)
C6—C5—H5	119.3	C14—C13—H13	121.0
C4—C5—H5	119.3	C12—C13—H13	121.0
C7—C6—C5	114.6 (2)	F1—C14—C13	118.6 (2)
C7—C6—C9	122.6 (2)	F1—C14—C15	117.9 (2)
C5—C6—C9	122.8 (2)	C13—C14—C15	123.5 (2)
C1—C8—O1	110.86 (17)	C14—C15—C16	117.9 (2)
C1—C8—C10	133.1 (2)	C14—C15—H15	121.0
O1—C8—C10	116.02 (19)	C16—C15—H15	121.0
O1—C7—C6	124.59 (19)	C11—C16—C15	119.5 (2)
O1—C7—C2	110.69 (17)	C11—C16—H16	120.3
C6—C7—C2	124.7 (2)	C15—C16—H16	120.3
C6—C9—H9A	109.5
O2—S1—C1—C8	139.60 (18)	C8—O1—C7—C2	−0.2 (2)
C11—S1—C1—C8	−109.88 (19)	C5—C6—C7—O1	−179.19 (19)
O2—S1—C1—C2	−37.4 (2)	C9—C6—C7—O1	1.3 (3)
C11—S1—C1—C2	73.1 (2)	C5—C6—C7—C2	1.0 (3)
C8—C1—C2—C7	0.5 (2)	C9—C6—C7—C2	−178.5 (2)
S1—C1—C2—C7	177.84 (16)	C3—C2—C7—O1	178.93 (17)
C8—C1—C2—C3	−178.4 (2)	C1—C2—C7—O1	−0.1 (2)
S1—C1—C2—C3	−1.0 (4)	C3—C2—C7—C6	−1.2 (3)
C7—C2—C3—C4	0.1 (3)	C1—C2—C7—C6	179.7 (2)
C1—C2—C3—C4	178.8 (2)	O2—S1—C11—C16	7.08 (19)
C2—C3—C4—C5	1.3 (3)	C1—S1—C11—C16	−104.19 (18)
C2—C3—C4—I1	−178.54 (14)	O2—S1—C11—C12	−168.41 (16)
C3—C4—C5—C6	−1.5 (3)	C1—S1—C11—C12	80.32 (18)
I1—C4—C5—C6	178.28 (16)	C16—C11—C12—C13	−0.2 (3)
C4—C5—C6—C7	0.4 (3)	S1—C11—C12—C13	175.24 (17)
C4—C5—C6—C9	179.8 (2)	C11—C12—C13—C14	−0.1 (3)
C2—C1—C8—O1	−0.6 (2)	C12—C13—C14—F1	−179.2 (2)
S1—C1—C8—O1	−178.17 (14)	C12—C13—C14—C15	1.3 (4)
C2—C1—C8—C10	−179.3 (2)	F1—C14—C15—C16	178.33 (19)
S1—C1—C8—C10	3.1 (4)	C13—C14—C15—C16	−2.2 (4)
C7—O1—C8—C1	0.5 (2)	C12—C11—C16—C15	−0.7 (3)
C7—O1—C8—C10	179.49 (18)	S1—C11—C16—C15	−176.06 (16)
C8—O1—C7—C6	179.94 (19)	C14—C15—C16—C11	1.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ii	0.95	2.51	3.444 (3)	169
C9—H9A···O2iii	0.98	2.48	3.437 (3)	165
C15—H15···O1iv	0.95	2.49	3.342 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.51	3.444 (3)	169
C9—H9A⋯O2ii	0.98	2.48	3.437 (3)	165
C15—H15⋯O1iii	0.95	2.49	3.342 (3)	149

Symmetry codes: (i) ; (ii) ; (iii) .