5-Chloro-3-ethyl­sulfinyl-2-(4-iodo­phen­yl)-7-methyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S160053681003134X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2277

https://doi.org/10.1107/S160053681003134X

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5-Chloro-3-ethylsulfinyl-2-(4-iodophenyl)-7-methyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 2 August 2010; accepted 5 August 2010; online 11 August 2010)

In the title compound, C₁₇H₁₄ClIO₂S, the 4-iodophenyl ring makes a dihedral angle of 1.61 (9)° with the benzofuran ring system. In the crystal, molecules are linked through a weak intermolecular C—H⋯O hydrogen bond and an I⋯O contact [3.416 (2) Å]. The ethyl group is disordered over two orientations with site-occupancy factors of 0.402 (7) and 0.598 (7).

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

Experimental

Crystal data

C₁₇H₁₄ClIO₂S
M_r = 444.69
Triclinic, $[P \overline 1]$
a = 7.8013 (2) Å
b = 10.4240 (3) Å
c = 11.6003 (3) Å
α = 115.962 (1)°
β = 98.040 (1)°
γ = 96.661 (1)°
V = 823.00 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.24 mm⁻¹
T = 173 K
0.48 × 0.34 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.473, T_max = 0.746
14721 measured reflections
3773 independent reflections
3408 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.065
S = 1.06
3773 reflections
221 parameters
28 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16A—H16B⋯O2ⁱ	0.97	2.40	3.297 (6)	154
Symmetry code: (i) -x, -y, -z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681003134X/is2588sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003134X/is2588Isup2.hkl

checkCIF report

Comment top

Many compounds containing a benzofuran ring have received considerable attention in view of their pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing studies of the substituent effect on the solid state structures of 3-ethylsulfinyl-2-(4-iodophenyl)-1-benzofuran analogues (Choi et al., 2010a, b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.007 (2) Å from the least-squares plane defined by the nine constituent atoms. The ethyl group is disordered over two positions with site–occupancy factors of 0.402 (7) (for atom labelled A) and 0.598 (7) (for atom labelled B) in Fig. 1. The dihedral angle formed by the benzofuran plane and the 4–iodophenyl ring is 1.61 (9)°. The molecular packing (Fig. 2) is stabilized by a weak intermolecular C—H···O hydrogen bond between the methylene H atom of the ethyl group and the oxygen of the S═O unit, with a C16A—H16B···O2ⁱ (Table 1). The crystal packing (Fig. 2) is further stabilized by an I···O halogen-bonding between the iodine and the oxygen of the S═O unit [I···O2ⁱⁱ = 3.416 (2) Å; C12—I···O2ⁱⁱ = 161.46 (7)°] (Politzer et al., 2007).

Related literature top

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

Experimental top

77% 3-chloroperoxybenzoic acid (157 mg, 0.7 mmol) was added in small portions to a stirred solution of 5-chloro-3-ethylsulfanyl-2-(4-iodophenyl)-7-methyl-1-benzofuran (300 mg, 0.7 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 457–458 K; R/_f = 0.64 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius. The ethyl group is disordered over two positions with site-occupancy factors, from refinement of 0.402 (7) and 0.598 (7).
	Fig. 2. C—H···O and I···O interactions (dotted lines) in the crystal structure of the title compound. The disordered component of the ethyl group, part B, has been omitted for clarity as have H atoms not involved in intermolecular contacts. [Symmetry codes: (i) - x, - y, - z; (ii) x + 1, y + 1, z + 1; (iii) x - 1 , y - 1, z - 1.]

5-Chloro-3-ethylsulfinyl-2-(4-iodophenyl)-7-methyl-1-benzofuran top

Crystal data top

C₁₇H₁₄ClIO₂S	Z = 2
M_r = 444.69	F(000) = 436
Triclinic, P1	D_x = 1.794 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8013 (2) Å	Cell parameters from 9231 reflections
b = 10.4240 (3) Å	θ = 2.2–27.5°
c = 11.6003 (3) Å	µ = 2.24 mm⁻¹
α = 115.962 (1)°	T = 173 K
β = 98.040 (1)°	Block, colourless
γ = 96.661 (1)°	0.48 × 0.34 × 0.16 mm
V = 823.00 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3773 independent reflections
Radiation source: rotating anode	3408 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.024
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.0°
φ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.473, T_max = 0.746	l = −15→15
14721 measured reflections

Refinement top

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)] = 0.024	Hydrogen site location: difference Fourier map
wR(F²) = 0.065	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.034P)² + 0.2748P] where P = (F_o² + 2F_c²)/3
3773 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.28 e Å⁻³
28 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

C₁₇H₁₄ClIO₂S	γ = 96.661 (1)°
M_r = 444.69	V = 823.00 (4) Å³
Triclinic, P1	Z = 2
a = 7.8013 (2) Å	Mo Kα radiation
b = 10.4240 (3) Å	µ = 2.24 mm⁻¹
c = 11.6003 (3) Å	T = 173 K
α = 115.962 (1)°	0.48 × 0.34 × 0.16 mm
β = 98.040 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3773 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3408 reflections with I > 2σ(I)
T_min = 0.473, T_max = 0.746	R_int = 0.024
14721 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	28 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.06	Δρ_max = 0.28 e Å⁻³
3773 reflections	Δρ_min = −0.60 e Å⁻³
221 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
I	0.64468 (2)	0.843070 (18)	0.633828 (13)	0.05745 (7)
Cl	−0.13606 (8)	0.12905 (7)	−0.54903 (5)	0.06029 (16)
S	0.05956 (8)	0.20738 (7)	0.00343 (6)	0.05340 (14)
O1	0.26320 (19)	0.55334 (15)	−0.03279 (13)	0.0397 (3)
O2	−0.1151 (3)	0.1273 (2)	−0.0800 (2)	0.0830 (7)
C3	−0.0084 (3)	0.2242 (2)	−0.2921 (2)	0.0432 (4)
H3	−0.0663	0.1352	−0.3031	0.052*
C1	0.1344 (3)	0.3441 (2)	−0.04020 (19)	0.0398 (4)
C2	0.0905 (3)	0.3316 (2)	−0.17052 (19)	0.0383 (4)
C4	−0.0153 (3)	0.2577 (2)	−0.3946 (2)	0.0440 (4)
C5	0.0668 (3)	0.3905 (2)	−0.3815 (2)	0.0450 (5)
H5	0.0567	0.4065	−0.4547	0.054*
C6	0.1637 (3)	0.4998 (2)	−0.2612 (2)	0.0413 (4)
C7	0.1723 (3)	0.4632 (2)	−0.15913 (18)	0.0377 (4)
C8	0.2378 (3)	0.4790 (2)	0.03875 (18)	0.0384 (4)
C9	0.3273 (3)	0.5601 (2)	0.17695 (19)	0.0396 (4)
C10	0.3167 (3)	0.5045 (3)	0.2654 (2)	0.0498 (5)
H10	0.2503	0.4120	0.2370	0.060*
C11	0.4045 (3)	0.5857 (3)	0.3958 (2)	0.0512 (5)
H11	0.3943	0.5481	0.4545	0.061*
C12	0.5061 (3)	0.7208 (2)	0.4386 (2)	0.0446 (5)
C13	0.5151 (4)	0.7794 (3)	0.3532 (2)	0.0611 (7)
H13	0.5815	0.8721	0.3825	0.073*
C14	0.4253 (4)	0.7001 (3)	0.2240 (2)	0.0590 (6)
H14	0.4303	0.7410	0.1673	0.071*
C15	0.2513 (4)	0.6454 (3)	−0.2418 (3)	0.0580 (6)
H15A	0.3745	0.6468	−0.2421	0.087*
H15B	0.2385	0.7197	−0.1593	0.087*
H15C	0.1971	0.6631	−0.3116	0.087*
C16A	0.2618 (6)	0.1332 (6)	0.0089 (5)	0.0561 (19)	0.402 (7)
H16A	0.3649	0.2108	0.0570	0.067*	0.402 (7)
H16B	0.2543	0.0697	0.0498	0.067*	0.402 (7)
C17A	0.2695 (15)	0.0509 (8)	−0.1310 (5)	0.074 (2)	0.402 (7)
H17A	0.1592	−0.0159	−0.1789	0.112*	0.402 (7)
H17B	0.3633	−0.0024	−0.1382	0.112*	0.402 (7)
H17C	0.2909	0.1174	−0.1665	0.112*	0.402 (7)
C16B	0.1842 (6)	0.0735 (5)	−0.0927 (4)	0.0586 (13)	0.598 (7)
H16C	0.1382	−0.0208	−0.0998	0.070*	0.598 (7)
H16D	0.1686	0.0643	−0.1806	0.070*	0.598 (7)
C17B	0.3749 (6)	0.1176 (7)	−0.0305 (6)	0.0832 (18)	0.598 (7)
H17D	0.4174	0.2156	−0.0140	0.125*	0.598 (7)
H17E	0.4386	0.0533	−0.0882	0.125*	0.598 (7)
H17F	0.3920	0.1126	0.0508	0.125*	0.598 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.05606 (11)	0.06525 (12)	0.03984 (9)	−0.00242 (7)	−0.00008 (6)	0.02082 (7)
Cl	0.0624 (3)	0.0565 (3)	0.0396 (3)	0.0026 (3)	0.0005 (2)	0.0076 (2)
S	0.0596 (3)	0.0483 (3)	0.0604 (3)	0.0012 (3)	0.0147 (3)	0.0339 (3)
O1	0.0480 (7)	0.0332 (7)	0.0359 (7)	0.0025 (6)	0.0051 (5)	0.0165 (5)
O2	0.0949 (15)	0.0656 (12)	0.0693 (12)	−0.0320 (11)	−0.0043 (11)	0.0322 (10)
C3	0.0463 (10)	0.0333 (10)	0.0431 (10)	0.0038 (8)	0.0085 (8)	0.0130 (8)
C1	0.0467 (10)	0.0359 (10)	0.0403 (10)	0.0077 (8)	0.0110 (8)	0.0202 (8)
C2	0.0414 (10)	0.0341 (9)	0.0392 (9)	0.0078 (8)	0.0097 (8)	0.0163 (8)
C4	0.0418 (10)	0.0425 (11)	0.0356 (9)	0.0073 (8)	0.0036 (8)	0.0090 (8)
C5	0.0496 (11)	0.0497 (12)	0.0378 (10)	0.0118 (9)	0.0089 (8)	0.0218 (9)
C6	0.0459 (10)	0.0390 (10)	0.0428 (10)	0.0083 (8)	0.0113 (8)	0.0217 (8)
C7	0.0404 (9)	0.0343 (9)	0.0358 (9)	0.0059 (7)	0.0067 (7)	0.0146 (7)
C8	0.0446 (10)	0.0359 (10)	0.0387 (9)	0.0088 (8)	0.0107 (8)	0.0199 (8)
C9	0.0414 (10)	0.0376 (10)	0.0379 (9)	0.0068 (8)	0.0071 (7)	0.0163 (8)
C10	0.0586 (13)	0.0419 (11)	0.0452 (11)	−0.0001 (10)	0.0009 (9)	0.0222 (9)
C11	0.0588 (13)	0.0525 (13)	0.0437 (11)	0.0043 (10)	0.0028 (9)	0.0273 (10)
C12	0.0428 (10)	0.0503 (12)	0.0363 (9)	0.0061 (9)	0.0046 (8)	0.0179 (9)
C13	0.0743 (16)	0.0502 (13)	0.0463 (12)	−0.0156 (12)	−0.0007 (11)	0.0216 (10)
C14	0.0800 (16)	0.0503 (13)	0.0409 (11)	−0.0101 (12)	0.0022 (11)	0.0246 (10)
C15	0.0709 (15)	0.0502 (13)	0.0551 (13)	−0.0005 (11)	0.0093 (11)	0.0306 (11)
C16A	0.076 (4)	0.041 (3)	0.050 (3)	0.005 (3)	0.002 (3)	0.025 (3)
C17A	0.112 (6)	0.057 (4)	0.062 (4)	0.028 (4)	0.015 (4)	0.033 (3)
C16B	0.084 (3)	0.044 (2)	0.051 (3)	0.017 (2)	0.019 (2)	0.0216 (19)
C17B	0.081 (4)	0.094 (4)	0.099 (4)	0.037 (3)	0.035 (3)	0.057 (3)

Geometric parameters (Å, º) top

I—C12	2.095 (2)	C10—C11	1.389 (3)
I—O2ⁱ	3.416 (2)	C10—H10	0.9300
Cl—C4	1.739 (2)	C11—C12	1.370 (3)
S—O2	1.466 (2)	C11—H11	0.9300
S—C1	1.774 (2)	C12—C13	1.378 (3)
S—C16A	1.841 (4)	C13—C14	1.381 (3)
S—C16B	1.842 (4)	C13—H13	0.9300
O1—C7	1.372 (2)	C14—H14	0.9300
O1—C8	1.379 (2)	C15—H15A	0.9600
C3—C4	1.374 (3)	C15—H15B	0.9600
C3—C2	1.397 (3)	C15—H15C	0.9600
C3—H3	0.9300	C16A—C17A	1.4807 (15)
C1—C8	1.368 (3)	C16A—H16A	0.9700
C1—C2	1.447 (3)	C16A—H16B	0.9700
C2—C7	1.386 (3)	C17A—H17A	0.9600
C4—C5	1.390 (3)	C17A—H17B	0.9600
C5—C6	1.389 (3)	C17A—H17C	0.9600
C5—H5	0.9300	C16B—C17B	1.4812 (15)
C6—C7	1.391 (3)	C16B—H16C	0.9700
C6—C15	1.495 (3)	C16B—H16D	0.9700
C8—C9	1.461 (3)	C17B—H17D	0.9600
C9—C10	1.389 (3)	C17B—H17E	0.9600
C9—C14	1.392 (3)	C17B—H17F	0.9600

C12—I—O2ⁱ	161.46 (7)	C12—C11—C10	120.4 (2)
O2—S—C1	108.18 (11)	C12—C11—H11	119.8
O2—S—C16A	126.7 (2)	C10—C11—H11	119.8
C1—S—C16A	99.2 (2)	C11—C12—C13	119.9 (2)
O2—S—C16B	96.09 (17)	C11—C12—I	121.10 (16)
C1—S—C16B	96.62 (17)	C13—C12—I	119.02 (16)
C7—O1—C8	106.81 (15)	C12—C13—C14	119.8 (2)
C4—C3—C2	116.20 (19)	C12—C13—H13	120.1
C4—C3—H3	121.9	C14—C13—H13	120.1
C2—C3—H3	121.9	C13—C14—C9	121.3 (2)
C8—C1—C2	106.99 (17)	C13—C14—H14	119.3
C8—C1—S	128.36 (16)	C9—C14—H14	119.3
C2—C1—S	124.63 (15)	C6—C15—H15A	109.5
C7—C2—C3	119.59 (18)	C6—C15—H15B	109.5
C7—C2—C1	105.15 (16)	H15A—C15—H15B	109.5
C3—C2—C1	135.26 (19)	C6—C15—H15C	109.5
C3—C4—C5	123.51 (19)	H15A—C15—H15C	109.5
C3—C4—Cl	118.70 (17)	H15B—C15—H15C	109.5
C5—C4—Cl	117.78 (17)	C17A—C16A—S	103.8 (4)
C6—C5—C4	121.43 (19)	C17A—C16A—H16A	111.0
C6—C5—H5	119.3	S—C16A—H16A	111.0
C4—C5—H5	119.3	C17A—C16A—H16B	111.0
C5—C6—C7	114.33 (19)	S—C16A—H16B	111.0
C5—C6—C15	123.3 (2)	H16A—C16A—H16B	109.0
C7—C6—C15	122.3 (2)	C17B—C16B—S	111.2 (3)
O1—C7—C2	110.77 (17)	C17B—C16B—H16C	109.4
O1—C7—C6	124.31 (18)	S—C16B—H16C	109.4
C2—C7—C6	124.93 (18)	C17B—C16B—H16D	109.4
C1—C8—O1	110.28 (16)	S—C16B—H16D	109.4
C1—C8—C9	135.71 (19)	H16C—C16B—H16D	108.0
O1—C8—C9	114.00 (16)	C16B—C17B—H17D	109.5
C10—C9—C14	117.86 (19)	C16B—C17B—H17E	109.5
C10—C9—C8	122.76 (19)	H17D—C17B—H17E	109.5
C14—C9—C8	119.37 (19)	C16B—C17B—H17F	109.5
C9—C10—C11	120.6 (2)	H17D—C17B—H17F	109.5
C9—C10—H10	119.7	H17E—C17B—H17F	109.5
C11—C10—H10	119.7

O2—S—C1—C8	147.2 (2)	C2—C1—C8—O1	−0.2 (2)
C16A—S—C1—C8	−79.1 (3)	S—C1—C8—O1	−178.82 (15)
C16B—S—C1—C8	−114.1 (2)	C2—C1—C8—C9	−179.1 (2)
O2—S—C1—C2	−31.1 (2)	S—C1—C8—C9	2.3 (4)
C16A—S—C1—C2	102.6 (2)	C7—O1—C8—C1	0.6 (2)
C16B—S—C1—C2	67.5 (2)	C7—O1—C8—C9	179.74 (16)
C4—C3—C2—C7	0.8 (3)	C1—C8—C9—C10	−1.6 (4)
C4—C3—C2—C1	−179.5 (2)	O1—C8—C9—C10	179.5 (2)
C8—C1—C2—C7	−0.2 (2)	C1—C8—C9—C14	179.6 (3)
S—C1—C2—C7	178.46 (15)	O1—C8—C9—C14	0.7 (3)
C8—C1—C2—C3	−179.9 (2)	C14—C9—C10—C11	−1.3 (4)
S—C1—C2—C3	−1.2 (4)	C8—C9—C10—C11	179.9 (2)
C2—C3—C4—C5	−1.2 (3)	C9—C10—C11—C12	−1.4 (4)
C2—C3—C4—Cl	180.00 (15)	C10—C11—C12—C13	2.9 (4)
C3—C4—C5—C6	0.3 (3)	C10—C11—C12—I	−178.48 (19)
Cl—C4—C5—C6	179.08 (17)	O2ⁱ—I—C12—C11	−167.99 (19)
C4—C5—C6—C7	1.0 (3)	O2ⁱ—I—C12—C13	10.6 (4)
C4—C5—C6—C15	−178.8 (2)	C11—C12—C13—C14	−1.6 (4)
C8—O1—C7—C2	−0.7 (2)	I—C12—C13—C14	179.7 (2)
C8—O1—C7—C6	179.17 (19)	C12—C13—C14—C9	−1.1 (4)
C3—C2—C7—O1	−179.68 (18)	C10—C9—C14—C13	2.5 (4)
C1—C2—C7—O1	0.6 (2)	C8—C9—C14—C13	−178.6 (3)
C3—C2—C7—C6	0.4 (3)	O2—S—C16A—C17A	48.1 (6)
C1—C2—C7—C6	−179.3 (2)	C1—S—C16A—C17A	−72.9 (5)
C5—C6—C7—O1	178.80 (18)	C16B—S—C16A—C17A	15.4 (5)
C15—C6—C7—O1	−1.5 (3)	O2—S—C16B—C17B	−177.3 (4)
C5—C6—C7—C2	−1.3 (3)	C1—S—C16B—C17B	73.5 (4)
C15—C6—C7—C2	178.4 (2)	C16A—S—C16B—C17B	−23.2 (4)

Symmetry code: (i) x+1, y+1, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16A—H16B···O2ⁱⁱ	0.97	2.40	3.297 (6)	154

Symmetry code: (ii) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄ClIO₂S
M_r	444.69
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.8013 (2), 10.4240 (3), 11.6003 (3)
α, β, γ (°)	115.962 (1), 98.040 (1), 96.661 (1)
V (Å³)	823.00 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.24
Crystal size (mm)	0.48 × 0.34 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.473, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14721, 3773, 3408
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.065, 1.06
No. of reflections	3773
No. of parameters	221
No. of restraints	28
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.60

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16A—H16B···O2ⁱ	0.97	2.40	3.297 (6)	154.4

Symmetry code: (i) −x, −y, −z.

References

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