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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1985
https://doi.org/10.1107/S1600536810026620

3-Ethyl­sulfinyl-2-(4-iodo­phen­yl)-5-methyl-1-benzo­furan

Hong Dae Choi,a Pil Ja Seo,a Byeng Wha Sonb and Uk Leeb*

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 July 2010; accepted 6 July 2010; online 10 July 2010)

In the title compound, C17H15IO2S, the 4-iodo­phenyl ring makes a dihedral angle of 35.39 (8)° with the plane of the benzofuran fragment. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O and C—H⋯π inter­actions, and an I⋯O contact [3.378 (2) Å]. The crystal structure also exhibits aromatic π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.495 (3) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006[Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]). For the structures of related 3-ethyl­sulfinyl-5-halo-2-(4-halophen­yl)-1-benzofuran derivatives, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o770.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o1043.],c[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010c). Acta Cryst. E66, o1862.]). For a review of halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]).

[Scheme 1]

Experimental

Crystal data

  • C17H15IO2S

  • Mr = 410.25

  • Monoclinic, P 21 /n

  • a = 10.1034 (3) Å

  • b = 13.1942 (4) Å

  • c = 11.9933 (3) Å

  • β = 92.634 (1)°

  • V = 1597.09 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.14 mm−1

  • T = 173 K

  • 0.32 × 0.27 × 0.09 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.551, Tmax = 0.834

  • 15129 measured reflections

  • 3667 independent reflections

  • 3366 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.069

  • S = 1.07

  • 3667 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.96 e Å−3

  • Δρmin = −0.69 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C16—H16B⋯O2i 0.97 2.60 3.341 (3) 134
C11—H11⋯Cgii 0.93 2.61 3.378 (3) 141
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810026620/bg2357sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026620/bg2357Isup2.hkl

checkCIF report


Comment top

The benzofuran ring system show interesting pharmacological properties such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) activities. 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-5-halo-2-(4-halophenyl)-1-benzofuran analogues (Choi et al., 2010a,b,c), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.021 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-iodophenyl ring is 35.39 (8)°. The crystal 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 C16—16B···O2i (Table 1), and by an I···O halogen-bonding between the iodine and the oxygen of the S═O unit [I···O2iii = 3.378 (2) Å; C12—I···O2iii = 162.46 (7)°] (Politzer et al., 2007). The molecular packing (Fig. 3) is further stabilized by an intermolecular C—H···π interaction between the 4-iodophenyl H atom and the benzene ring of a neighbouring molecule, with a C11—H11···Cgii (Table 1), and by an aromatic π–π interaction between the benzene rings of neighbouring molecules, with a Cg···Cgv distance of 3.495 (3) Å (Cg is the centroid of the C2–C7 benzene ring).

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-5-halo-2-(4-halophenyl)-1-benzofuran derivatives, see: Choi et al. (2010a,b,c). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

77% 3-chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-ethylsulfanyl-2-(4-iodophenyl)-5-methyl-1-benzofurans (315 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, 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, 1:2 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 431–432 K; Rf = 0.63 (hexane–ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in tetrahydrofuran at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for aryl, 0.96 Å for methylene and methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and methylene H atoms, and 1.5Ueq(C) for methyl H atoms.

Structure description top

The benzofuran ring system show interesting pharmacological properties such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) activities. 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-5-halo-2-(4-halophenyl)-1-benzofuran analogues (Choi et al., 2010a,b,c), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.021 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-iodophenyl ring is 35.39 (8)°. The crystal 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 C16—16B···O2i (Table 1), and by an I···O halogen-bonding between the iodine and the oxygen of the S═O unit [I···O2iii = 3.378 (2) Å; C12—I···O2iii = 162.46 (7)°] (Politzer et al., 2007). The molecular packing (Fig. 3) is further stabilized by an intermolecular C—H···π interaction between the 4-iodophenyl H atom and the benzene ring of a neighbouring molecule, with a C11—H11···Cgii (Table 1), and by an aromatic π–π interaction between the benzene rings of neighbouring molecules, with a Cg···Cgv distance of 3.495 (3) Å (Cg is the centroid of the C2–C7 benzene ring).

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-5-halo-2-(4-halophenyl)-1-benzofuran derivatives, see: Choi et al. (2010a,b,c). 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
[Figure 1] 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.
[Figure 2] Fig. 2. C–H···O and I···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) -x + 1, -y, -z + 1; (iii) x, y, z + 1; (iv) x, y, z -1 .]
[Figure 3] Fig. 3. C–H···π, and π–π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (ii) x + 1/2, -y + 1/2, z + 1/2; (v) -x + 1, -y + 1, -z + 1; (vi) x - 1/2, -y + 1/2, z - 1/2; (vii) -x + 3/2, y + 1/2, -z + 3/2.]
3-Ethylsulfinyl-2-(4-iodophenyl)-5-methyl-1-benzofuran top
Crystal data top
C17H15IO2SF(000) = 808
Mr = 410.25Dx = 1.706 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9921 reflections
a = 10.1034 (3) Åθ = 2.3–27.5°
b = 13.1942 (4) ŵ = 2.14 mm−1
c = 11.9933 (3) ÅT = 173 K
β = 92.634 (1)°Block, colourless
V = 1597.09 (8) Å30.32 × 0.27 × 0.09 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer		3667 independent reflections
Radiation source: rotating anode3366 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.025
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 2.3°
φ and ω scansh = −8→13
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −17→10
Tmin = 0.551, Tmax = 0.834l = −15→15
15129 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: difference Fourier map
wR(F2) = 0.069H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0328P)2 + 1.5593P]
where P = (Fo2 + 2Fc2)/3
3667 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.96 e Å−3
0 restraintsΔρmin = −0.69 e Å−3
Crystal data top
C17H15IO2SV = 1597.09 (8) Å3
Mr = 410.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.1034 (3) ŵ = 2.14 mm−1
b = 13.1942 (4) ÅT = 173 K
c = 11.9933 (3) Å0.32 × 0.27 × 0.09 mm
β = 92.634 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3667 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3366 reflections with I > 2σ(I)
Tmin = 0.551, Tmax = 0.834Rint = 0.025
15129 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.069H-atom parameters constrained
S = 1.07Δρmax = 0.96 e Å−3
3667 reflectionsΔρmin = −0.69 e Å−3
192 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
xyzUiso*/Ueq
I0.491732 (16)0.129285 (13)1.209790 (12)0.03433 (7)
S0.44476 (6)0.12571 (4)0.57565 (5)0.02928 (13)
O20.5466 (2)0.12728 (14)0.48973 (19)0.0451 (5)
O10.36148 (16)0.39156 (12)0.71054 (13)0.0269 (3)
C10.4080 (2)0.25304 (17)0.60955 (18)0.0254 (4)
C20.3800 (2)0.33516 (18)0.53236 (19)0.0253 (4)
C30.3795 (2)0.34768 (18)0.41673 (19)0.0281 (5)
H30.39640.29310.37040.034*
C40.3531 (2)0.44313 (19)0.3722 (2)0.0292 (5)
C50.3273 (2)0.52457 (18)0.4432 (2)0.0300 (5)
H50.31080.58810.41200.036*
C60.3253 (2)0.51387 (18)0.5580 (2)0.0290 (5)
H60.30680.56800.60450.035*
C70.3525 (2)0.41812 (17)0.59933 (18)0.0253 (4)
C80.3968 (2)0.29066 (17)0.71460 (18)0.0255 (4)
C90.4144 (2)0.24931 (17)0.82760 (18)0.0261 (4)
C100.5115 (2)0.1770 (2)0.85308 (19)0.0309 (5)
H100.56330.15250.79690.037*
C110.5319 (3)0.14090 (19)0.9612 (2)0.0315 (5)
H110.59660.09230.97750.038*
C120.4547 (2)0.17826 (18)1.04487 (18)0.0276 (5)
C130.3559 (2)0.24893 (18)1.02076 (19)0.0288 (5)
H130.30340.27251.07690.035*
C140.3359 (2)0.28432 (18)0.91224 (19)0.0283 (5)
H140.26970.33170.89590.034*
C150.3528 (3)0.4598 (2)0.2475 (2)0.0384 (6)
H15A0.41240.41270.21510.058*
H15B0.38100.52780.23260.058*
H15C0.26490.44960.21560.058*
C160.2900 (3)0.0929 (2)0.5052 (2)0.0372 (6)
H16A0.27040.14190.44650.045*
H16B0.29840.02700.47050.045*
C170.1766 (3)0.0902 (2)0.5821 (3)0.0486 (7)
H17A0.19750.04460.64280.073*
H17B0.09810.06730.54170.073*
H17C0.16200.15690.61090.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I0.03738 (11)0.04108 (12)0.02435 (9)0.00488 (7)−0.00062 (7)0.00094 (6)
S0.0299 (3)0.0259 (3)0.0322 (3)0.0037 (2)0.0021 (2)−0.0051 (2)
O20.0406 (11)0.0417 (11)0.0547 (13)0.0043 (8)0.0192 (10)−0.0043 (9)
O10.0306 (8)0.0241 (8)0.0258 (8)0.0025 (6)−0.0021 (6)−0.0040 (6)
C10.0272 (11)0.0226 (11)0.0264 (10)0.0002 (8)0.0006 (8)−0.0023 (8)
C20.0228 (10)0.0249 (11)0.0283 (11)−0.0021 (9)0.0007 (8)−0.0019 (9)
C30.0284 (11)0.0286 (11)0.0275 (11)−0.0032 (9)0.0035 (9)−0.0028 (9)
C40.0242 (11)0.0340 (12)0.0294 (11)−0.0053 (9)0.0023 (9)0.0032 (9)
C50.0259 (11)0.0265 (11)0.0373 (12)−0.0018 (9)−0.0010 (9)0.0042 (9)
C60.0267 (11)0.0257 (11)0.0344 (12)0.0002 (9)−0.0014 (9)−0.0040 (9)
C70.0235 (10)0.0271 (11)0.0253 (10)−0.0013 (9)−0.0010 (8)−0.0028 (8)
C80.0243 (10)0.0242 (11)0.0278 (10)0.0020 (8)−0.0005 (8)−0.0027 (8)
C90.0260 (11)0.0277 (11)0.0244 (10)0.0001 (9)−0.0017 (8)−0.0032 (8)
C100.0283 (12)0.0400 (14)0.0244 (10)0.0086 (10)0.0020 (9)−0.0033 (9)
C110.0288 (12)0.0362 (13)0.0290 (11)0.0079 (10)−0.0031 (9)−0.0034 (9)
C120.0293 (11)0.0298 (12)0.0234 (10)−0.0015 (9)−0.0014 (9)−0.0037 (9)
C130.0308 (12)0.0295 (12)0.0265 (11)0.0034 (9)0.0035 (9)−0.0048 (9)
C140.0280 (11)0.0258 (11)0.0310 (11)0.0049 (9)−0.0002 (9)−0.0032 (9)
C150.0434 (15)0.0424 (15)0.0298 (12)−0.0048 (12)0.0044 (10)0.0068 (11)
C160.0397 (14)0.0326 (13)0.0392 (13)−0.0019 (11)−0.0007 (11)−0.0048 (11)
C170.0383 (15)0.0398 (15)0.068 (2)−0.0042 (12)0.0118 (14)−0.0039 (14)
Geometric parameters (Å, º) top
I—C122.098 (2)C9—C101.392 (3)
I—O2i3.378 (2)C9—C141.395 (3)
S—O21.490 (2)C10—C111.388 (3)
S—C11.772 (2)C10—H100.9300
S—C161.796 (3)C11—C121.390 (3)
O1—C71.378 (3)C11—H110.9300
O1—C81.379 (3)C12—C131.386 (3)
C1—C81.364 (3)C13—C141.389 (3)
C1—C21.445 (3)C13—H130.9300
C2—C71.393 (3)C14—H140.9300
C2—C31.396 (3)C15—H15A0.9600
C3—C41.389 (3)C15—H15B0.9600
C3—H30.9300C15—H15C0.9600
C4—C51.402 (3)C16—C171.503 (4)
C4—C151.513 (3)C16—H16A0.9700
C5—C61.386 (3)C16—H16B0.9700
C5—H50.9300C17—H17A0.9600
C6—C71.380 (3)C17—H17B0.9600
C6—H60.9300C17—H17C0.9600
C8—C91.464 (3)
C12—I—O2i162.46 (7)C11—C10—H10119.6
O2—S—C1107.71 (11)C9—C10—H10119.6
O2—S—C16107.00 (13)C10—C11—C12119.3 (2)
C1—S—C1698.58 (12)C10—C11—H11120.4
C7—O1—C8106.57 (17)C12—C11—H11120.4
C8—C1—C2107.27 (19)C13—C12—C11120.7 (2)
C8—C1—S125.75 (18)C13—C12—I119.95 (16)
C2—C1—S126.94 (17)C11—C12—I119.34 (18)
C7—C2—C3119.2 (2)C12—C13—C14119.6 (2)
C7—C2—C1104.97 (19)C12—C13—H13120.2
C3—C2—C1135.8 (2)C14—C13—H13120.2
C4—C3—C2118.7 (2)C13—C14—C9120.5 (2)
C4—C3—H3120.6C13—C14—H14119.8
C2—C3—H3120.6C9—C14—H14119.8
C3—C4—C5120.0 (2)C4—C15—H15A109.5
C3—C4—C15120.3 (2)C4—C15—H15B109.5
C5—C4—C15119.8 (2)H15A—C15—H15B109.5
C6—C5—C4122.4 (2)C4—C15—H15C109.5
C6—C5—H5118.8H15A—C15—H15C109.5
C4—C5—H5118.8H15B—C15—H15C109.5
C7—C6—C5116.0 (2)C17—C16—S112.9 (2)
C7—C6—H6122.0C17—C16—H16A109.0
C5—C6—H6122.0S—C16—H16A109.0
O1—C7—C6125.7 (2)C17—C16—H16B109.0
O1—C7—C2110.6 (2)S—C16—H16B109.0
C6—C7—C2123.6 (2)H16A—C16—H16B107.8
C1—C8—O1110.56 (19)C16—C17—H17A109.5
C1—C8—C9135.1 (2)C16—C17—H17B109.5
O1—C8—C9114.37 (18)H17A—C17—H17B109.5
C10—C9—C14119.0 (2)C16—C17—H17C109.5
C10—C9—C8120.9 (2)H17A—C17—H17C109.5
C14—C9—C8120.1 (2)H17B—C17—H17C109.5
C11—C10—C9120.9 (2)
O2—S—C1—C8−134.9 (2)C2—C1—C8—O10.8 (3)
C16—S—C1—C8114.1 (2)S—C1—C8—O1−177.22 (16)
O2—S—C1—C247.4 (2)C2—C1—C8—C9−178.6 (2)
C16—S—C1—C2−63.6 (2)S—C1—C8—C93.3 (4)
C8—C1—C2—C7−0.4 (3)C7—O1—C8—C1−1.0 (2)
S—C1—C2—C7177.68 (17)C7—O1—C8—C9178.56 (19)
C8—C1—C2—C3177.1 (3)C1—C8—C9—C1034.9 (4)
S—C1—C2—C3−4.8 (4)O1—C8—C9—C10−144.5 (2)
C7—C2—C3—C40.8 (3)C1—C8—C9—C14−146.9 (3)
C1—C2—C3—C4−176.4 (2)O1—C8—C9—C1433.7 (3)
C2—C3—C4—C5−0.2 (3)C14—C9—C10—C11−1.0 (4)
C2—C3—C4—C15179.5 (2)C8—C9—C10—C11177.2 (2)
C3—C4—C5—C6−0.7 (4)C9—C10—C11—C12−0.4 (4)
C15—C4—C5—C6179.6 (2)C10—C11—C12—C131.6 (4)
C4—C5—C6—C71.0 (3)C10—C11—C12—I−176.97 (19)
C8—O1—C7—C6−176.9 (2)C11—C12—C13—C14−1.4 (4)
C8—O1—C7—C20.8 (2)I—C12—C13—C14177.17 (18)
C5—C6—C7—O1177.0 (2)C12—C13—C14—C90.0 (4)
C5—C6—C7—C2−0.3 (3)C10—C9—C14—C131.2 (4)
C3—C2—C7—O1−178.3 (2)C8—C9—C14—C13−177.1 (2)
C1—C2—C7—O1−0.3 (2)O2—S—C16—C17−179.0 (2)
C3—C2—C7—C6−0.6 (4)C1—S—C16—C17−67.5 (2)
C1—C2—C7—C6177.4 (2)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C16—H16B···O2ii0.972.603.341 (3)134
C11—H11···Cgiii0.932.613.378 (3)141
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H15IO2S
Mr410.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)10.1034 (3), 13.1942 (4), 11.9933 (3)
β (°) 92.634 (1)
V (Å3)1597.09 (8)
Z4
Radiation typeMo Kα
µ (mm−1)2.14
Crystal size (mm)0.32 × 0.27 × 0.09
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.551, 0.834
No. of measured, independent and
observed [I > 2σ(I)] reflections		15129, 3667, 3366
Rint0.025
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.069, 1.07
No. of reflections3667
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.96, −0.69

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
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C16—H16B···O2i0.972.603.341 (3)133.5
C11—H11···Cgii0.932.613.378 (3)140.9
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2.
 

References

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1985
https://doi.org/10.1107/S1600536810026620
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