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

In the title compound, C(16)H(12)ClIO(2)S, the 4-iodo-phenyl ring is rotated out of the benzofuran plane by 9.4 (1)°. In the crystal structure, inter-molecular C-H⋯π inter-actions and short inter-molecular I⋯O contacts [3.142 (2) Å] are observed.

Related literature

For the crystal structures of related 3-ethyl­sulfinyl-2-(4-iodo­phen­yl)-1-benzofuran derivatives, see: Choi et al. (2010 ▶). For a review on halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C16H12ClIO2S

M = 430.67

Monoclinic,

a = 11.9782 (3) Å

b = 10.4604 (3) Å

c = 12.9624 (4) Å

β = 107.827 (1)°

V = 1546.16 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.38 mm−1

T = 173 K

0.35 × 0.25 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.514, T max = 0.746

14190 measured reflections

3549 independent reflections

3252 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.054

S = 1.67

3549 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.91 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/S1600536810033581/nc2194sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033581/nc2194Isup2.hkl

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

C16H12ClIO2S	F(000) = 840
Mr = 430.67	Dx = 1.850 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8003 reflections
a = 11.9782 (3) Å	θ = 2.6–27.5°
b = 10.4604 (3) Å	µ = 2.38 mm−1
c = 12.9624 (4) Å	T = 173 K
β = 107.827 (1)°	Block, colourless
V = 1546.16 (8) Å3	0.35 × 0.25 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3549 independent reflections
Radiation source: rotating anode	3252 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.032
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.6°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.514, Tmax = 0.746	l = −16→15
14190 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) = 0.054	H-atom parameters constrained
S = 1.67	w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3
3549 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −0.91 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
I	0.020729 (12)	0.410793 (14)	0.735141 (13)	0.03083 (6)
Cl	0.91427 (5)	0.77704 (6)	0.50411 (5)	0.03458 (14)
S	0.66881 (5)	0.44141 (5)	0.74904 (5)	0.02532 (12)
O1	0.45082 (12)	0.67491 (14)	0.53906 (12)	0.0240 (3)
O2	0.75087 (15)	0.37662 (16)	0.69934 (15)	0.0382 (4)
C1	0.59438 (18)	0.56061 (19)	0.65608 (17)	0.0217 (4)
C2	0.64728 (18)	0.6403 (2)	0.59295 (17)	0.0215 (4)
C3	0.76078 (18)	0.6605 (2)	0.58850 (18)	0.0243 (5)
H3	0.8249	0.6181	0.6349	0.029*
C4	0.77369 (19)	0.74651 (19)	0.51177 (18)	0.0249 (5)
C5	0.6793 (2)	0.8095 (2)	0.43905 (19)	0.0287 (5)
H5	0.6921	0.8647	0.3875	0.034*
C6	0.5667 (2)	0.7897 (2)	0.44369 (19)	0.0293 (5)
H6	0.5023	0.8309	0.3965	0.035*
C7	0.55461 (18)	0.7064 (2)	0.52149 (17)	0.0229 (4)
C8	0.47620 (18)	0.58480 (19)	0.62118 (17)	0.0220 (4)
C9	0.37422 (17)	0.5421 (2)	0.65070 (17)	0.0222 (4)
C10	0.2620 (2)	0.5747 (2)	0.5829 (2)	0.0274 (5)
H10	0.2541	0.6210	0.5199	0.033*
C11	0.16345 (19)	0.5382 (2)	0.60939 (19)	0.0290 (5)
H11	0.0895	0.5625	0.5654	0.035*
C12	0.17458 (18)	0.4656 (2)	0.70127 (18)	0.0242 (5)
C13	0.2839 (2)	0.4300 (2)	0.7671 (2)	0.0335 (6)
H13	0.2911	0.3797	0.8279	0.040*
C14	0.38293 (19)	0.4693 (2)	0.74239 (19)	0.0320 (5)
H14	0.4566	0.4467	0.7880	0.038*
C15	0.7574 (2)	0.5465 (2)	0.8530 (2)	0.0342 (6)
H15A	0.8221	0.4984	0.9004	0.041*
H15B	0.7900	0.6136	0.8192	0.041*
C16	0.6874 (3)	0.6064 (2)	0.9197 (2)	0.0447 (7)
H16A	0.6264	0.6589	0.8739	0.067*
H16B	0.7382	0.6579	0.9760	0.067*
H16C	0.6531	0.5402	0.9516	0.067*

	U11	U22	U33	U12	U13	U23
I	0.02630 (9)	0.03230 (10)	0.03857 (11)	−0.00398 (6)	0.01689 (7)	−0.00332 (6)
Cl	0.0289 (3)	0.0336 (3)	0.0473 (4)	−0.0040 (2)	0.0206 (3)	−0.0008 (3)
S	0.0215 (3)	0.0245 (3)	0.0300 (3)	0.0028 (2)	0.0080 (2)	0.0053 (2)
O1	0.0194 (7)	0.0275 (8)	0.0247 (8)	0.0010 (6)	0.0061 (6)	0.0032 (6)
O2	0.0343 (9)	0.0375 (9)	0.0468 (11)	0.0128 (8)	0.0186 (8)	0.0069 (8)
C1	0.0218 (10)	0.0211 (10)	0.0218 (12)	0.0017 (8)	0.0058 (8)	0.0008 (8)
C2	0.0222 (10)	0.0205 (10)	0.0223 (11)	0.0002 (8)	0.0073 (8)	−0.0019 (8)
C3	0.0210 (10)	0.0236 (11)	0.0282 (12)	0.0021 (9)	0.0076 (9)	0.0000 (9)
C4	0.0237 (10)	0.0240 (11)	0.0295 (13)	−0.0030 (9)	0.0120 (9)	−0.0048 (9)
C5	0.0338 (12)	0.0277 (12)	0.0265 (13)	−0.0031 (10)	0.0121 (10)	0.0036 (9)
C6	0.0278 (11)	0.0307 (12)	0.0274 (13)	0.0023 (10)	0.0054 (9)	0.0047 (10)
C7	0.0202 (10)	0.0246 (11)	0.0235 (12)	−0.0010 (8)	0.0062 (9)	−0.0017 (9)
C8	0.0228 (10)	0.0217 (10)	0.0205 (11)	0.0003 (8)	0.0052 (8)	−0.0018 (8)
C9	0.0191 (10)	0.0229 (10)	0.0243 (12)	−0.0004 (8)	0.0061 (8)	−0.0027 (9)
C10	0.0254 (11)	0.0255 (11)	0.0305 (13)	0.0005 (9)	0.0072 (9)	0.0069 (9)
C11	0.0191 (10)	0.0288 (11)	0.0362 (14)	0.0018 (9)	0.0042 (9)	0.0045 (10)
C12	0.0200 (10)	0.0251 (11)	0.0298 (13)	−0.0021 (9)	0.0110 (9)	−0.0055 (9)
C13	0.0288 (12)	0.0459 (15)	0.0280 (14)	0.0019 (11)	0.0121 (10)	0.0084 (11)
C14	0.0198 (11)	0.0482 (15)	0.0274 (13)	0.0027 (10)	0.0063 (9)	0.0059 (11)
C15	0.0295 (12)	0.0372 (13)	0.0291 (14)	−0.0065 (11)	−0.0012 (10)	0.0073 (10)
C16	0.0638 (19)	0.0336 (14)	0.0331 (15)	−0.0055 (13)	0.0093 (13)	−0.0016 (11)

I—C12	2.101 (2)	C6—H6	0.9300
I—O2i	3.1422 (17)	C8—C9	1.458 (3)
Cl—C4	1.746 (2)	C9—C14	1.388 (3)
S—O2	1.4928 (17)	C9—C10	1.404 (3)
S—C1	1.773 (2)	C10—C11	1.380 (3)
S—C15	1.810 (2)	C10—H10	0.9300
O1—C7	1.371 (2)	C11—C12	1.384 (3)
O1—C8	1.384 (2)	C11—H11	0.9300
C1—C8	1.371 (3)	C12—C13	1.378 (3)
C1—C2	1.444 (3)	C13—C14	1.382 (3)
C2—C7	1.392 (3)	C13—H13	0.9300
C2—C3	1.394 (3)	C14—H14	0.9300
C3—C4	1.385 (3)	C15—C16	1.513 (4)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.396 (3)	C15—H15B	0.9700
C5—C6	1.384 (3)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.374 (3)	C16—H16C	0.9600
C12—I—O2i	158.24 (7)	C14—C9—C8	122.93 (19)
O2—S—C1	106.65 (10)	C10—C9—C8	118.68 (19)
O2—S—C15	106.48 (11)	C11—C10—C9	120.4 (2)
C1—S—C15	97.87 (11)	C11—C10—H10	119.8
C7—O1—C8	107.13 (15)	C9—C10—H10	119.8
C8—C1—C2	107.12 (18)	C10—C11—C12	120.1 (2)
C8—C1—S	127.41 (16)	C10—C11—H11	120.0
C2—C1—S	125.09 (16)	C12—C11—H11	120.0
C7—C2—C3	119.10 (19)	C13—C12—C11	120.3 (2)
C7—C2—C1	105.36 (18)	C13—C12—I	121.68 (17)
C3—C2—C1	135.5 (2)	C11—C12—I	118.04 (15)
C4—C3—C2	116.9 (2)	C12—C13—C14	119.8 (2)
C4—C3—H3	121.5	C12—C13—H13	120.1
C2—C3—H3	121.5	C14—C13—H13	120.1
C3—C4—C5	123.1 (2)	C13—C14—C9	121.1 (2)
C3—C4—Cl	118.77 (17)	C13—C14—H14	119.4
C5—C4—Cl	118.11 (17)	C9—C14—H14	119.4
C6—C5—C4	119.9 (2)	C16—C15—S	112.07 (18)
C6—C5—H5	120.0	C16—C15—H15A	109.2
C4—C5—H5	120.0	S—C15—H15A	109.2
C7—C6—C5	116.7 (2)	C16—C15—H15B	109.2
C7—C6—H6	121.6	S—C15—H15B	109.2
C5—C6—H6	121.6	H15A—C15—H15B	107.9
O1—C7—C6	125.38 (19)	C15—C16—H16A	109.5
O1—C7—C2	110.43 (18)	C15—C16—H16B	109.5
C6—C7—C2	124.19 (19)	H16A—C16—H16B	109.5
C1—C8—O1	109.93 (18)	C15—C16—H16C	109.5
C1—C8—C9	136.1 (2)	H16A—C16—H16C	109.5
O1—C8—C9	113.98 (17)	H16B—C16—H16C	109.5
C14—C9—C10	118.39 (19)
O2—S—C1—C8	132.8 (2)	S—C1—C8—O1	−172.77 (15)
C15—S—C1—C8	−117.3 (2)	C2—C1—C8—C9	−177.9 (2)
O2—S—C1—C2	−39.1 (2)	S—C1—C8—C9	9.1 (4)
C15—S—C1—C2	70.8 (2)	C7—O1—C8—C1	0.7 (2)
C8—C1—C2—C7	−1.2 (2)	C7—O1—C8—C9	179.31 (17)
S—C1—C2—C7	172.11 (16)	C1—C8—C9—C14	9.4 (4)
C8—C1—C2—C3	−179.9 (2)	O1—C8—C9—C14	−168.7 (2)
S—C1—C2—C3	−6.6 (4)	C1—C8—C9—C10	−170.0 (2)
C7—C2—C3—C4	0.0 (3)	O1—C8—C9—C10	11.9 (3)
C1—C2—C3—C4	178.6 (2)	C14—C9—C10—C11	2.0 (3)
C2—C3—C4—C5	−1.6 (3)	C8—C9—C10—C11	−178.6 (2)
C2—C3—C4—Cl	179.06 (16)	C9—C10—C11—C12	−2.1 (3)
C3—C4—C5—C6	1.8 (3)	C10—C11—C12—C13	0.4 (3)
Cl—C4—C5—C6	−178.83 (18)	C10—C11—C12—I	−178.92 (17)
C4—C5—C6—C7	−0.4 (3)	O2i—I—C12—C13	−172.72 (15)
C8—O1—C7—C6	177.6 (2)	O2i—I—C12—C11	6.6 (3)
C8—O1—C7—C2	−1.5 (2)	C11—C12—C13—C14	1.4 (4)
C5—C6—C7—O1	179.7 (2)	I—C12—C13—C14	−179.32 (18)
C5—C6—C7—C2	−1.3 (3)	C12—C13—C14—C9	−1.5 (4)
C3—C2—C7—O1	−179.39 (19)	C10—C9—C14—C13	−0.2 (4)
C1—C2—C7—O1	1.6 (2)	C8—C9—C14—C13	−179.6 (2)
C3—C2—C7—C6	1.5 (3)	O2—S—C15—C16	−172.90 (17)
C1—C2—C7—C6	−177.5 (2)	C1—S—C15—C16	77.08 (19)
C2—C1—C8—O1	0.3 (2)

Cg is the centroid of the C2–C7 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cgii	0.97	3.04	3.750 (3)	131.

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cgi	0.97	3.04	3.750 (3)	131

Symmetry code: (i) .