5-Iodo-2-phenyl-3-phenyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536809024556

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1809

doi:10.1107/S1600536809024556

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5-Iodo-2-phenyl-3-phenylsulfinyl-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 25 June 2009; accepted 26 June 2009; online 11 July 2009)

In the title compound, C₂₀H₁₃IO₂S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment; the phenyl ring is almost perpendicular to this plane [83.84 (5)°]. The phenyl ring in the 2-position is rotated out of the benzofuran plane, making a dihedral angle of 40.47 (5)°. The crystal structure is stabilized by non-classical intermolecular C—H⋯O interactions, and by an I⋯O halogen bond of 3.124 (1) Å [C—I⋯O = 165.84 (5)°].

Related literature

For the crystal structures of similar 5-iodo-1-benzofuran derivatives, see: Choi et al. (2007a ,b ). For a review of halogen interactions, see: Politzer et al. (2007 ). The Cambridge Structural Database (version 5.28; Allen et al., 2002 ) has 39 compounds with C–I⋯O=S contact distances less than or equal to 3.3 Å.

Experimental

Crystal data

C₂₀H₁₃IO₂S
M_r = 444.26
Triclinic, $[P \overline 1]$
a = 9.3544 (4) Å
b = 9.7565 (5) Å
c = 10.2808 (5) Å
α = 113.381 (1)°
β = 92.640 (1)°
γ = 98.047 (1)°
V = 847.42 (7) Å³
Z = 2
Mo Kα radiation
μ = 2.02 mm⁻¹
T = 273 K
0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.467, T_max = 0.665
7217 measured reflections
3616 independent reflections
3503 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.017
wR(F²) = 0.044
S = 1.07
3616 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.93	2.53	3.438 (2)	165
C19—H19⋯O1ⁱⁱ	0.93	2.59	3.483 (2)	162
C20—H20⋯O2ⁱⁱⁱ	0.93	2.53	3.412 (2)	159
Symmetry codes: (i) -x, -y, -z; (ii) x, y, z+1; (iii) -x, -y, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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: 10.1107/S1600536809024556/ng2605sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024556/ng2605Isup2.hkl

checkCIF report

Comment top

This work is related to our communications on the synthesis and structures of 5-iodo-1-benzofuran analogues, viz. 5-iodo-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007a) and 5-iodo-2-methyl-3-phenylsulfinyl-1-benzofuran (Choi et al., 2007b). We present the crystal structure of the title compound (I), 5-iodo-2-phenyl-3-phenylsulfinyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle in (I) formed by the planes of the benzofuran and 2-phenyl rings is 40.47 (5)°, and the phenyl ring (C15-C20) with 83.84 (5)° lies toward the benzofuran plane. The crystal packing (Fig. 2) is stabilized by non-classical intermolecular C–H···O interactions; the first between an H atom of the 2-phenyl ring and the oxygen of the S═O unit, with a C10–H10···O2ⁱ, the second between a phenyl H atom of the phenylsulfinyl substituent and the furan O atom, with a C19–H19···O1ⁱⁱ, the third between a phenyl H atom of the phenylsulfinyl substituent and the oxygen of the S═O unit, with a C20–H20···O2ⁱⁱⁱ, respectively (Table 1 and Fig. 2; symmetry code as in Fig. 2). The molecular packing (Fig. 2) is further stabilized by an I···O halogen bond (Politzer et al., 2007) between the iodine atom and the oxygen of neighbouring S═O unit, with an I···O^iv (Symmetry code as in Fig. 2). The observed I···O separation of 3.124 (1) Å and the nearly linear C–I···O angle of 165.84 (5)° are typical for such halogen bonds. A search of Cambridge Structural Database (version 5.28; Allen, 2002) revealed 39 compounds with C–I···O═S contact distances equal to or less than 3.3 Å.

Related literature top

For the crystal structures of similar 5-iodo-1-benzofuran derivatives, see: Choi et al. (2007a,b). For a review of halogen interactions, see: Politzer et al. (2007). The Cambridge Structural Database (version 5.28; Allen et al., 2002) has 39 compounds with C–I···O═S contact distances equal to or less than 3.3 Å.

Experimental top

The 77% 3-chloroperoxybenzoic acid (123 mg, 0.55 mmol) was added in small portions to a stirred solution of 5-iodo-2-phenyl-3-phenylsulfanyl-1-benzofuran (214 mg, 0.5 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 423-424 K; R_f = 0.74 (hexane-ethyl acetate, 2:1 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.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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.
	Fig. 2. The C–H···O hydrogen bond and I···O halogen bond (dotted lines) in the title compound. [Symmetry code: (i) -x, -y, -z; (ii) x, y, z + 1; (iii) -x, -y, -z + 1; (iv) -x, -y + 1, -z + 1; (v) x, y, z - 1.]

5-Iodo-2-phenyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₂₀H₁₃IO₂S	Z = 2
M_r = 444.26	F(000) = 436
Triclinic, P1	D_x = 1.741 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3544 (4) Å	Cell parameters from 6672 reflections
b = 9.7565 (5) Å	θ = 2.2–27.5°
c = 10.2808 (5) Å	µ = 2.02 mm⁻¹
α = 113.381 (1)°	T = 273 K
β = 92.640 (1)°	Block, colorless
γ = 98.047 (1)°	0.40 × 0.40 × 0.20 mm
V = 847.42 (7) Å³

Data collection top

Bruker SMART CCD diffractometer	3616 independent reflections
Radiation source: fine-focus sealed tube	3503 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 2.2°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→12
T_min = 0.467, T_max = 0.665	l = −13→12
7217 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)] = 0.017	Hydrogen site location: difference Fourier map
wR(F²) = 0.044	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0224P)² + 0.4472P] where P = (F_o² + 2F_c²)/3
3616 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₂₀H₁₃IO₂S	γ = 98.047 (1)°
M_r = 444.26	V = 847.42 (7) Å³
Triclinic, P1	Z = 2
a = 9.3544 (4) Å	Mo Kα radiation
b = 9.7565 (5) Å	µ = 2.02 mm⁻¹
c = 10.2808 (5) Å	T = 273 K
α = 113.381 (1)°	0.40 × 0.40 × 0.20 mm
β = 92.640 (1)°

Data collection top

Bruker SMART CCD diffractometer	3616 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	3503 reflections with I > 2σ(I)
T_min = 0.467, T_max = 0.665	R_int = 0.014
7217 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	0 restraints
wR(F²) = 0.044	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
3616 reflections	Δρ_min = −0.66 e Å⁻³
217 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
I	0.041308 (11)	0.682844 (11)	0.391884 (12)	0.02610 (5)
S	0.15151 (4)	0.00846 (5)	0.27065 (4)	0.02113 (8)
O1	0.23863 (13)	0.11727 (14)	−0.05193 (12)	0.0244 (2)
O2	0.01344 (13)	0.05325 (15)	0.32919 (13)	0.0278 (3)
C1	0.19488 (18)	0.09925 (19)	0.15550 (17)	0.0213 (3)
C2	0.16806 (17)	0.24593 (19)	0.16717 (17)	0.0212 (3)
C3	0.12402 (18)	0.37088 (19)	0.27157 (18)	0.0229 (3)
H3	0.1038	0.3714	0.3595	0.027*
C4	0.11164 (18)	0.49421 (19)	0.23915 (18)	0.0231 (3)
C5	0.14158 (19)	0.4962 (2)	0.10730 (19)	0.0263 (3)
H5	0.1329	0.5815	0.0901	0.032*
C6	0.1841 (2)	0.3719 (2)	0.00232 (19)	0.0274 (4)
H6	0.2037	0.3707	−0.0860	0.033*
C7	0.19590 (18)	0.24964 (19)	0.03641 (18)	0.0231 (3)
C8	0.23701 (18)	0.02755 (19)	0.02314 (17)	0.0222 (3)
C9	0.28197 (18)	−0.11933 (19)	−0.05014 (18)	0.0223 (3)
C10	0.23677 (19)	−0.2044 (2)	−0.19558 (19)	0.0265 (3)
H10	0.1800	−0.1671	−0.2463	0.032*
C11	0.2777 (2)	−0.3454 (2)	−0.2632 (2)	0.0315 (4)
H11	0.2461	−0.4036	−0.3592	0.038*
C12	0.3653 (2)	−0.4000 (2)	−0.1890 (2)	0.0347 (4)
H12	0.3929	−0.4939	−0.2355	0.042*
C13	0.4117 (2)	−0.3148 (2)	−0.0455 (2)	0.0344 (4)
H13	0.4706	−0.3515	0.0041	0.041*
C14	0.3700 (2)	−0.1747 (2)	0.0242 (2)	0.0286 (4)
H14	0.4009	−0.1178	0.1206	0.034*
C15	0.29386 (18)	0.10909 (19)	0.41498 (17)	0.0216 (3)
C16	0.4258 (2)	0.1827 (2)	0.3995 (2)	0.0333 (4)
H16	0.4411	0.1914	0.3142	0.040*
C17	0.5347 (2)	0.2429 (3)	0.5131 (2)	0.0412 (5)
H17	0.6233	0.2931	0.5041	0.049*
C18	0.5124 (2)	0.2288 (2)	0.6400 (2)	0.0342 (4)
H18	0.5864	0.2684	0.7152	0.041*
C19	0.3803 (2)	0.1560 (2)	0.65465 (19)	0.0287 (4)
H19	0.3655	0.1473	0.7400	0.034*
C20	0.26963 (19)	0.09587 (19)	0.54241 (18)	0.0244 (3)
H20	0.1805	0.0474	0.5523	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.02785 (7)	0.02109 (7)	0.03128 (7)	0.00645 (4)	0.00755 (5)	0.01148 (5)
S	0.02433 (19)	0.02144 (19)	0.02157 (18)	0.00522 (15)	0.00503 (15)	0.01221 (15)
O1	0.0307 (6)	0.0269 (6)	0.0205 (5)	0.0099 (5)	0.0065 (5)	0.0129 (5)
O2	0.0216 (6)	0.0364 (7)	0.0300 (6)	0.0054 (5)	0.0069 (5)	0.0178 (6)
C1	0.0226 (7)	0.0228 (8)	0.0218 (7)	0.0055 (6)	0.0034 (6)	0.0120 (6)
C2	0.0206 (7)	0.0244 (8)	0.0222 (7)	0.0045 (6)	0.0026 (6)	0.0130 (6)
C3	0.0241 (8)	0.0257 (8)	0.0228 (8)	0.0058 (6)	0.0054 (6)	0.0133 (7)
C4	0.0213 (8)	0.0225 (8)	0.0268 (8)	0.0049 (6)	0.0042 (6)	0.0107 (7)
C5	0.0285 (8)	0.0267 (9)	0.0306 (9)	0.0068 (7)	0.0027 (7)	0.0182 (7)
C6	0.0324 (9)	0.0342 (9)	0.0242 (8)	0.0100 (7)	0.0064 (7)	0.0190 (7)
C7	0.0235 (8)	0.0271 (8)	0.0223 (8)	0.0071 (6)	0.0038 (6)	0.0129 (7)
C8	0.0223 (7)	0.0264 (8)	0.0219 (8)	0.0052 (6)	0.0022 (6)	0.0137 (7)
C9	0.0215 (7)	0.0250 (8)	0.0228 (8)	0.0045 (6)	0.0063 (6)	0.0115 (7)
C10	0.0267 (8)	0.0279 (9)	0.0245 (8)	0.0028 (7)	0.0032 (7)	0.0108 (7)
C11	0.0371 (10)	0.0266 (9)	0.0260 (9)	−0.0001 (7)	0.0091 (7)	0.0070 (7)
C12	0.0409 (11)	0.0231 (9)	0.0413 (11)	0.0096 (8)	0.0169 (9)	0.0118 (8)
C13	0.0364 (10)	0.0333 (10)	0.0414 (11)	0.0150 (8)	0.0092 (8)	0.0201 (9)
C14	0.0316 (9)	0.0296 (9)	0.0266 (8)	0.0098 (7)	0.0038 (7)	0.0121 (7)
C15	0.0225 (8)	0.0233 (8)	0.0227 (8)	0.0081 (6)	0.0039 (6)	0.0117 (6)
C16	0.0260 (9)	0.0531 (12)	0.0292 (9)	0.0036 (8)	0.0057 (7)	0.0262 (9)
C17	0.0238 (9)	0.0654 (15)	0.0401 (11)	−0.0027 (9)	0.0013 (8)	0.0312 (11)
C18	0.0286 (9)	0.0472 (11)	0.0289 (9)	0.0068 (8)	−0.0010 (7)	0.0179 (8)
C19	0.0370 (10)	0.0330 (9)	0.0218 (8)	0.0109 (8)	0.0069 (7)	0.0151 (7)
C20	0.0272 (8)	0.0239 (8)	0.0264 (8)	0.0071 (6)	0.0079 (7)	0.0133 (7)

Geometric parameters (Å, º) top

I—C4	2.104 (2)	C10—C11	1.391 (3)
I—O2ⁱ	3.124 (1)	C10—H10	0.9300
S—O2	1.497 (1)	C11—C12	1.387 (3)
S—C1	1.768 (2)	C11—H11	0.9300
S—C15	1.799 (2)	C12—C13	1.386 (3)
O1—C8	1.377 (2)	C12—H12	0.9300
O1—C7	1.378 (2)	C13—C14	1.389 (3)
C1—C8	1.367 (2)	C13—H13	0.9300
C1—C2	1.447 (2)	C14—H14	0.9300
C2—C7	1.394 (2)	C15—C16	1.388 (2)
C2—C3	1.397 (2)	C15—C20	1.392 (2)
C3—C4	1.388 (2)	C16—C17	1.387 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.404 (2)	C17—C18	1.386 (3)
C5—C6	1.389 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.382 (3)
C6—C7	1.387 (2)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.389 (3)
C8—C9	1.463 (2)	C19—H19	0.9300
C9—C14	1.397 (2)	C20—H20	0.9300
C9—C10	1.401 (2)

C4—I—O2ⁱ	165.84 (5)	C11—C10—H10	120.4
O2—S—C1	107.63 (7)	C9—C10—H10	120.4
O2—S—C15	106.00 (8)	C12—C11—C10	120.66 (17)
C1—S—C15	100.57 (8)	C12—C11—H11	119.7
C8—O1—C7	106.38 (12)	C10—C11—H11	119.7
C8—C1—C2	107.02 (14)	C13—C12—C11	120.13 (17)
C8—C1—S	123.64 (13)	C13—C12—H12	119.9
C2—C1—S	128.38 (12)	C11—C12—H12	119.9
C7—C2—C3	119.26 (15)	C12—C13—C14	119.94 (18)
C7—C2—C1	104.91 (14)	C12—C13—H13	120.0
C3—C2—C1	135.83 (15)	C14—C13—H13	120.0
C4—C3—C2	117.47 (15)	C13—C14—C9	120.11 (17)
C4—C3—H3	121.3	C13—C14—H14	119.9
C2—C3—H3	121.3	C9—C14—H14	119.9
C3—C4—C5	122.37 (16)	C16—C15—C20	120.95 (16)
C3—C4—I	118.65 (12)	C16—C15—S	123.40 (13)
C5—C4—I	118.96 (12)	C20—C15—S	115.34 (13)
C6—C5—C4	120.55 (15)	C17—C16—C15	119.05 (17)
C6—C5—H5	119.7	C17—C16—H16	120.5
C4—C5—H5	119.7	C15—C16—H16	120.5
C7—C6—C5	116.34 (16)	C18—C17—C16	120.50 (18)
C7—C6—H6	121.8	C18—C17—H17	119.8
C5—C6—H6	121.8	C16—C17—H17	119.8
O1—C7—C6	125.17 (15)	C19—C18—C17	120.03 (18)
O1—C7—C2	110.82 (14)	C19—C18—H18	120.0
C6—C7—C2	124.00 (16)	C17—C18—H18	120.0
C1—C8—O1	110.87 (14)	C18—C19—C20	120.30 (16)
C1—C8—C9	133.30 (15)	C18—C19—H19	119.8
O1—C8—C9	115.81 (14)	C20—C19—H19	119.8
C14—C9—C10	119.94 (16)	C19—C20—C15	119.15 (16)
C14—C9—C8	120.26 (15)	C19—C20—H20	120.4
C10—C9—C8	119.80 (15)	C15—C20—H20	120.4
C11—C10—C9	119.19 (17)

O2—S—C1—C8	−134.10 (15)	C7—O1—C8—C1	−0.06 (18)
C15—S—C1—C8	115.21 (15)	C7—O1—C8—C9	−178.86 (14)
O2—S—C1—C2	33.18 (17)	C1—C8—C9—C14	−39.3 (3)
C15—S—C1—C2	−77.52 (16)	O1—C8—C9—C14	139.16 (16)
C8—C1—C2—C7	0.54 (18)	C1—C8—C9—C10	140.9 (2)
S—C1—C2—C7	−168.40 (13)	O1—C8—C9—C10	−40.7 (2)
C8—C1—C2—C3	−179.78 (19)	C14—C9—C10—C11	1.5 (3)
S—C1—C2—C3	11.3 (3)	C8—C9—C10—C11	−178.63 (16)
C7—C2—C3—C4	−0.6 (2)	C9—C10—C11—C12	−1.6 (3)
C1—C2—C3—C4	179.73 (18)	C10—C11—C12—C13	0.7 (3)
C2—C3—C4—C5	0.0 (2)	C11—C12—C13—C14	0.2 (3)
C2—C3—C4—I	178.71 (12)	C12—C13—C14—C9	−0.2 (3)
C3—C4—C5—C6	0.6 (3)	C10—C9—C14—C13	−0.7 (3)
I—C4—C5—C6	−178.10 (13)	C8—C9—C14—C13	179.52 (17)
C4—C5—C6—C7	−0.5 (3)	O2—S—C15—C16	−135.76 (16)
C8—O1—C7—C6	179.37 (17)	C1—S—C15—C16	−23.80 (17)
C8—O1—C7—C2	0.42 (18)	O2—S—C15—C20	50.62 (14)
C5—C6—C7—O1	−178.91 (16)	C1—S—C15—C20	162.58 (13)
C5—C6—C7—C2	−0.1 (3)	C20—C15—C16—C17	0.3 (3)
C3—C2—C7—O1	179.66 (14)	S—C15—C16—C17	−172.99 (17)
C1—C2—C7—O1	−0.59 (18)	C15—C16—C17—C18	0.5 (3)
C3—C2—C7—C6	0.7 (3)	C16—C17—C18—C19	−0.8 (4)
C1—C2—C7—C6	−179.56 (16)	C17—C18—C19—C20	0.4 (3)
C2—C1—C8—O1	−0.30 (19)	C18—C19—C20—C15	0.4 (3)
S—C1—C8—O1	169.29 (11)	C16—C15—C20—C19	−0.7 (3)
C2—C1—C8—C9	178.21 (17)	S—C15—C20—C19	173.06 (13)
S—C1—C8—C9	−12.2 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱⁱ	0.93	2.53	3.438 (2)	165
C19—H19···O1ⁱⁱⁱ	0.93	2.59	3.483 (2)	162
C20—H20···O2^iv	0.93	2.53	3.412 (2)	159

Symmetry codes: (ii) −x, −y, −z; (iii) x, y, z+1; (iv) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃IO₂S
M_r	444.26
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	9.3544 (4), 9.7565 (5), 10.2808 (5)
α, β, γ (°)	113.381 (1), 92.640 (1), 98.047 (1)
V (Å³)	847.42 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.02
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.467, 0.665
No. of measured, independent and observed [I > 2σ(I)] reflections	7217, 3616, 3503
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.044, 1.07
No. of reflections	3616
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.66

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C10—H10···O2ⁱ	0.93	2.53	3.438 (2)	164.8
C19—H19···O1ⁱⁱ	0.93	2.59	3.483 (2)	161.6
C20—H20···O2ⁱⁱⁱ	0.93	2.53	3.412 (2)	158.6

Symmetry codes: (i) −x, −y, −z; (ii) x, y, z+1; (iii) −x, −y, −z+1.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3745. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o3851. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page o1809

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