2-(Tritylsulfan­yl)ethyl 3-iodo­benzoate

Zhu, X.; Ng, S.W.

doi:10.1107/S1600536811036427

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2631

https://doi.org/10.1107/S1600536811036427

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2-(Tritylsulfanyl)ethyl 3-iodobenzoate

Xin Zhu ^a and Seik Weng Ng ^b ^*

^aHenan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and, Chemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 3 September 2011; accepted 6 September 2011; online 14 September 2011)

The triphenylmethyl group in the title compound, C₂₈H₂₃IO₂S, has the methine carbon slightly flattened out [ΣC_phenyl—C—C_phenyl = 332.8 (6) °]. The –C–O–C–C–S– chain connecting the triphenylmethyl group and the aromatic ring adopts an extended zigzag conformation, these five atoms being approximately co-planar (r.m.s. deviation 0.260 Å).

Related literature

For the 2-iodobenzoate analog, see: Zhu et al. (2011 ).

Experimental

Crystal data

C₂₈H₂₃IO₂S
M_r = 550.42
Triclinic, $[P \overline 1]$
a = 8.1634 (8) Å
b = 8.8413 (9) Å
c = 18.9968 (18) Å
α = 89.493 (1)°
β = 79.270 (2)°
γ = 65.663 (1)°
V = 1223.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.42 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS, Sheldrick, 1996 ) T_min = 0.601, T_max = 0.765
5948 measured reflections
4254 independent reflections
3375 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.126
S = 1.02
4254 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −1.33 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811036427/zs2142sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036427/zs2142Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036427/zs2142Isup3.cml

checkCIF report

Comment top

Triphenylmethyl is an important S-protecting group that prevents a thiol group from reacting with sensitive functional groups. The compound C₂₈H₂₃IO₂S (Scheme I) was synthesized for the purpose of examining copper(I) chloride-catalyzed cleavage reactions, the present study following a previous structural determination of the 2-iodobenzoate analog (Zhu et al., 2011). The methine carbon is slightly flattened out (ΣC_phenyl–C–C_phenyl 332.8 (6) °) owing to decreased crowding by the S atom. The –C–O–C–C–S– chain connecting the triphenylmethyl group and the aromatic ring adopts an extended zigzag conformation, these five atoms lying on an approximate plane (r.m.s. deviation 0.260 Å) (Fig. 1).

Related literature top

For the 2-iodobenzoate analog, see: Zhu et al. (2011).

Experimental top

A solution of 3-iodobenzoic acid (0.74 g, 3 mmol), dicyclohexylcarbodiimide (1.03 g, 5 mmol) and 4-dimethylaminopyridine (0.61 g, 8 mmol) in THF (20 ml) was stirred for an hour. 2-(tritylthio)ethanol (0.96 g, 3 mmol) was added. The reaction was stirred for 36 h. The compound was purified by column chromatography with petroleum ether–acetone (2:1) as the eluent and was isolated upon evaporation of the solvent as yellow crystals (2.30 g, 80% yield).

Structure description top

For the 2-iodobenzoate analog, see: Zhu et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₈H₂₃IO₂S at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

2-(Tritylsulfanyl)ethyl 3-iodobenzoate top

Crystal data top

C₂₈H₂₃IO₂S	Z = 2
M_r = 550.42	F(000) = 552
Triclinic, P1	D_x = 1.494 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1634 (8) Å	Cell parameters from 2381 reflections
b = 8.8413 (9) Å	θ = 2.9–25.0°
c = 18.9968 (18) Å	µ = 1.42 mm⁻¹
α = 89.493 (1)°	T = 293 K
β = 79.270 (2)°	Prism, yellow
γ = 65.663 (1)°	0.40 × 0.35 × 0.20 mm
V = 1223.9 (2) Å³

Data collection top

Bruker SMART APEX diffractometer	4254 independent reflections
Radiation source: fine-focus sealed tube	3375 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	h = −9→9
T_min = 0.601, T_max = 0.765	k = −10→10
5948 measured reflections	l = −22→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0509P)² + 1.4533P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4254 reflections	Δρ_max = 0.89 e Å⁻³
290 parameters	Δρ_min = −1.33 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0354 (19)

Crystal data top

C₂₈H₂₃IO₂S	γ = 65.663 (1)°
M_r = 550.42	V = 1223.9 (2) Å³
Triclinic, P1	Z = 2
a = 8.1634 (8) Å	Mo Kα radiation
b = 8.8413 (9) Å	µ = 1.42 mm⁻¹
c = 18.9968 (18) Å	T = 293 K
α = 89.493 (1)°	0.40 × 0.35 × 0.20 mm
β = 79.270 (2)°

Data collection top

Bruker SMART APEX diffractometer	4254 independent reflections
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	3375 reflections with I > 2σ(I)
T_min = 0.601, T_max = 0.765	R_int = 0.018
5948 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.02	Δρ_max = 0.89 e Å⁻³
4254 reflections	Δρ_min = −1.33 e Å⁻³
290 parameters

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

	x	y	z	U_iso*/U_eq
I1	0.70737 (7)	0.61227 (5)	0.60081 (2)	0.1219 (3)
S1	0.73375 (12)	−0.09689 (11)	0.27224 (4)	0.0482 (2)
O1	0.9395 (4)	−0.0436 (4)	0.37588 (14)	0.0733 (8)
O2	1.0491 (6)	0.1484 (5)	0.3642 (2)	0.1083 (13)
C1	0.5442 (4)	−0.0134 (3)	0.16643 (17)	0.0376 (7)
C2	0.5437 (4)	0.0440 (4)	0.09843 (18)	0.0446 (7)
H2	0.6475	−0.0058	0.0623	0.054*
C3	0.3903 (5)	0.1748 (5)	0.0836 (2)	0.0569 (9)
H3	0.3920	0.2127	0.0378	0.068*
C4	0.2358 (5)	0.2489 (5)	0.1365 (2)	0.0626 (10)
H4	0.1326	0.3365	0.1265	0.075*
C5	0.2343 (5)	0.1929 (4)	0.2040 (2)	0.0591 (10)
H5	0.1303	0.2440	0.2400	0.071*
C6	0.3854 (4)	0.0617 (4)	0.21896 (19)	0.0482 (8)
H6	0.3815	0.0227	0.2646	0.058*
C7	0.8838 (4)	−0.1952 (4)	0.12723 (16)	0.0362 (6)
C8	0.9698 (4)	−0.3353 (4)	0.08007 (18)	0.0455 (7)
H8	0.9232	−0.4155	0.0825	0.055*
C9	1.1256 (5)	−0.3583 (5)	0.0288 (2)	0.0576 (9)
H9	1.1830	−0.4543	−0.0022	0.069*
C10	1.1947 (5)	−0.2414 (5)	0.0235 (2)	0.0565 (9)
H10	1.2975	−0.2564	−0.0115	0.068*
C11	1.1113 (5)	−0.1011 (5)	0.0702 (2)	0.0549 (9)
H11	1.1589	−0.0216	0.0673	0.066*
C12	0.9576 (4)	−0.0776 (4)	0.12155 (18)	0.0462 (8)
H12	0.9024	0.0180	0.1528	0.055*
C13	0.6642 (4)	−0.3178 (4)	0.18842 (17)	0.0385 (7)
C14	0.7540 (5)	−0.4510 (4)	0.2265 (2)	0.0510 (8)
H14	0.8427	−0.4480	0.2502	0.061*
C15	0.7132 (5)	−0.5887 (4)	0.2296 (2)	0.0601 (10)
H15	0.7749	−0.6769	0.2555	0.072*
C16	0.5843 (5)	−0.5972 (4)	0.1953 (2)	0.0625 (10)
H16	0.5566	−0.6895	0.1982	0.075*
C17	0.4959 (6)	−0.4673 (5)	0.1566 (3)	0.0659 (11)
H17	0.4090	−0.4722	0.1323	0.079*
C18	0.5353 (5)	−0.3291 (4)	0.1533 (2)	0.0557 (9)
H18	0.4738	−0.2420	0.1269	0.067*
C19	0.7098 (4)	−0.1647 (4)	0.18310 (16)	0.0364 (6)
C20	0.9669 (5)	−0.2308 (5)	0.2817 (2)	0.0594 (9)
H20A	0.9645	−0.3123	0.3160	0.071*
H20B	1.0386	−0.2898	0.2359	0.071*
C21	1.0527 (6)	−0.1264 (6)	0.3073 (2)	0.0700 (11)
H21A	1.1769	−0.1958	0.3127	0.084*
H21B	1.0567	−0.0452	0.2731	0.084*
C22	0.9472 (6)	0.0942 (6)	0.3973 (2)	0.0688 (11)
C23	0.8168 (6)	0.1760 (6)	0.4656 (2)	0.0694 (11)
C24	0.8162 (6)	0.3195 (6)	0.4935 (2)	0.0754 (12)
H24	0.8964	0.3620	0.4696	0.090*
C25	0.6974 (7)	0.4010 (7)	0.5568 (2)	0.0841 (14)
C26	0.5784 (8)	0.3367 (10)	0.5919 (3)	0.1035 (19)
H26	0.4970	0.3913	0.6342	0.124*
C27	0.5801 (8)	0.1935 (11)	0.5645 (3)	0.114 (2)
H27	0.5005	0.1506	0.5886	0.137*
C28	0.6994 (7)	0.1116 (8)	0.5013 (2)	0.0902 (16)
H28	0.7003	0.0140	0.4829	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.1472 (5)	0.1016 (4)	0.0882 (3)	−0.0278 (3)	−0.0128 (3)	−0.0138 (2)
S1	0.0494 (5)	0.0535 (5)	0.0438 (5)	−0.0241 (4)	−0.0075 (4)	−0.0034 (4)
O1	0.085 (2)	0.115 (2)	0.0464 (15)	−0.0680 (19)	−0.0136 (14)	0.0030 (15)
O2	0.131 (3)	0.129 (3)	0.082 (2)	−0.093 (3)	0.032 (2)	−0.024 (2)
C1	0.0354 (15)	0.0313 (15)	0.0498 (18)	−0.0184 (13)	−0.0062 (13)	0.0012 (13)
C2	0.0424 (17)	0.0432 (17)	0.0494 (19)	−0.0198 (15)	−0.0074 (14)	0.0049 (14)
C3	0.054 (2)	0.056 (2)	0.065 (2)	−0.0259 (18)	−0.0183 (18)	0.0207 (18)
C4	0.045 (2)	0.045 (2)	0.092 (3)	−0.0110 (16)	−0.018 (2)	0.0169 (19)
C5	0.0410 (19)	0.047 (2)	0.077 (3)	−0.0113 (16)	0.0002 (17)	0.0031 (18)
C6	0.0423 (18)	0.0459 (18)	0.053 (2)	−0.0179 (15)	−0.0026 (15)	0.0062 (15)
C7	0.0326 (15)	0.0367 (15)	0.0403 (16)	−0.0152 (12)	−0.0078 (12)	0.0046 (12)
C8	0.0420 (17)	0.0408 (17)	0.0540 (19)	−0.0196 (14)	−0.0045 (15)	0.0006 (14)
C9	0.050 (2)	0.053 (2)	0.059 (2)	−0.0162 (17)	0.0039 (17)	−0.0092 (17)
C10	0.0441 (19)	0.065 (2)	0.058 (2)	−0.0262 (17)	0.0034 (16)	0.0054 (18)
C11	0.051 (2)	0.055 (2)	0.070 (2)	−0.0343 (17)	−0.0078 (17)	0.0108 (18)
C12	0.0462 (18)	0.0416 (17)	0.055 (2)	−0.0243 (15)	−0.0048 (15)	−0.0004 (14)
C13	0.0369 (15)	0.0309 (15)	0.0475 (17)	−0.0172 (13)	−0.0005 (13)	0.0001 (12)
C14	0.0467 (19)	0.0408 (18)	0.067 (2)	−0.0198 (15)	−0.0118 (16)	0.0074 (16)
C15	0.061 (2)	0.0365 (18)	0.079 (3)	−0.0205 (17)	−0.006 (2)	0.0131 (17)
C16	0.061 (2)	0.0404 (19)	0.089 (3)	−0.0312 (18)	0.003 (2)	−0.0027 (18)
C17	0.064 (2)	0.055 (2)	0.095 (3)	−0.038 (2)	−0.023 (2)	0.002 (2)
C18	0.058 (2)	0.0453 (19)	0.076 (3)	−0.0291 (17)	−0.0241 (19)	0.0108 (17)
C19	0.0361 (15)	0.0337 (15)	0.0412 (16)	−0.0173 (13)	−0.0058 (12)	0.0012 (12)
C20	0.055 (2)	0.071 (2)	0.058 (2)	−0.0274 (19)	−0.0214 (18)	0.0077 (18)
C21	0.064 (2)	0.106 (3)	0.054 (2)	−0.048 (2)	−0.0177 (19)	0.004 (2)
C22	0.069 (3)	0.097 (3)	0.052 (2)	−0.048 (2)	−0.010 (2)	0.004 (2)
C23	0.064 (2)	0.105 (3)	0.047 (2)	−0.041 (2)	−0.0158 (19)	0.011 (2)
C24	0.074 (3)	0.097 (3)	0.054 (2)	−0.037 (3)	−0.007 (2)	0.007 (2)
C25	0.078 (3)	0.107 (4)	0.055 (3)	−0.025 (3)	−0.016 (2)	0.003 (2)
C26	0.078 (3)	0.166 (6)	0.058 (3)	−0.049 (4)	−0.002 (2)	−0.006 (3)
C27	0.097 (4)	0.203 (7)	0.066 (3)	−0.092 (5)	0.000 (3)	0.006 (4)
C28	0.088 (3)	0.147 (5)	0.059 (3)	−0.075 (3)	−0.008 (2)	0.008 (3)

Geometric parameters (Å, º) top

I1—C25	2.091 (6)	C12—H12	0.9300
S1—C20	1.823 (4)	C13—C18	1.383 (5)
S1—C19	1.872 (3)	C13—C14	1.385 (5)
O1—C22	1.317 (5)	C13—C19	1.542 (4)
O1—C21	1.449 (5)	C14—C15	1.387 (5)
O2—C22	1.202 (5)	C14—H14	0.9300
C1—C2	1.384 (4)	C15—C16	1.363 (6)
C1—C6	1.392 (4)	C15—H15	0.9300
C1—C19	1.542 (4)	C16—C17	1.372 (6)
C2—C3	1.384 (5)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.384 (5)
C3—C4	1.374 (6)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.371 (6)	C20—C21	1.498 (5)
C4—H4	0.9300	C20—H20A	0.9700
C5—C6	1.377 (5)	C20—H20B	0.9700
C5—H5	0.9300	C21—H21A	0.9700
C6—H6	0.9300	C21—H21B	0.9700
C7—C8	1.378 (4)	C22—C23	1.486 (6)
C7—C12	1.395 (4)	C23—C24	1.378 (7)
C7—C19	1.532 (4)	C23—C28	1.379 (6)
C8—C9	1.392 (5)	C24—C25	1.382 (6)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.361 (5)	C25—C26	1.385 (8)
C9—H9	0.9300	C26—C27	1.367 (9)
C10—C11	1.375 (5)	C26—H26	0.9300
C10—H10	0.9300	C27—C28	1.384 (8)
C11—C12	1.379 (5)	C27—H27	0.9300
C11—H11	0.9300	C28—H28	0.9300

C20—S1—C19	105.86 (16)	C15—C16—H16	120.6
C22—O1—C21	117.5 (3)	C17—C16—H16	120.6
C2—C1—C6	118.2 (3)	C16—C17—C18	120.5 (4)
C2—C1—C19	121.6 (3)	C16—C17—H17	119.8
C6—C1—C19	120.0 (3)	C18—C17—H17	119.8
C3—C2—C1	120.7 (3)	C17—C18—C13	121.4 (3)
C3—C2—H2	119.6	C17—C18—H18	119.3
C1—C2—H2	119.6	C13—C18—H18	119.3
C4—C3—C2	120.2 (4)	C7—C19—C1	110.8 (2)
C4—C3—H3	119.9	C7—C19—C13	112.6 (2)
C2—C3—H3	119.9	C1—C19—C13	109.4 (2)
C5—C4—C3	119.7 (3)	C7—C19—S1	109.38 (19)
C5—C4—H4	120.2	C1—C19—S1	102.89 (19)
C3—C4—H4	120.2	C13—C19—S1	111.3 (2)
C4—C5—C6	120.5 (3)	C21—C20—S1	109.3 (3)
C4—C5—H5	119.8	C21—C20—H20A	109.8
C6—C5—H5	119.8	S1—C20—H20A	109.8
C5—C6—C1	120.7 (3)	C21—C20—H20B	109.8
C5—C6—H6	119.7	S1—C20—H20B	109.8
C1—C6—H6	119.7	H20A—C20—H20B	108.3
C8—C7—C12	117.8 (3)	O1—C21—C20	106.6 (3)
C8—C7—C19	122.0 (3)	O1—C21—H21A	110.4
C12—C7—C19	120.2 (3)	C20—C21—H21A	110.4
C7—C8—C9	120.8 (3)	O1—C21—H21B	110.4
C7—C8—H8	119.6	C20—C21—H21B	110.4
C9—C8—H8	119.6	H21A—C21—H21B	108.6
C10—C9—C8	120.6 (3)	O2—C22—O1	123.0 (4)
C10—C9—H9	119.7	O2—C22—C23	123.6 (4)
C8—C9—H9	119.7	O1—C22—C23	113.4 (4)
C9—C10—C11	119.5 (3)	C24—C23—C28	120.0 (4)
C9—C10—H10	120.3	C24—C23—C22	118.1 (4)
C11—C10—H10	120.3	C28—C23—C22	121.9 (5)
C12—C11—C10	120.4 (3)	C23—C24—C25	120.5 (5)
C12—C11—H11	119.8	C23—C24—H24	119.7
C10—C11—H11	119.8	C25—C24—H24	119.7
C11—C12—C7	120.9 (3)	C24—C25—C26	119.2 (5)
C11—C12—H12	119.6	C24—C25—I1	119.9 (4)
C7—C12—H12	119.6	C26—C25—I1	120.8 (4)
C18—C13—C14	117.4 (3)	C27—C26—C25	120.3 (5)
C18—C13—C19	120.9 (3)	C27—C26—H26	119.9
C14—C13—C19	121.6 (3)	C25—C26—H26	119.9
C13—C14—C15	120.7 (3)	C26—C27—C28	120.6 (5)
C13—C14—H14	119.7	C26—C27—H27	119.7
C15—C14—H14	119.7	C28—C27—H27	119.7
C16—C15—C14	121.2 (4)	C23—C28—C27	119.5 (6)
C16—C15—H15	119.4	C23—C28—H28	120.3
C14—C15—H15	119.4	C27—C28—H28	120.3
C15—C16—C17	118.8 (3)

C6—C1—C2—C3	1.3 (5)	C2—C1—C19—C13	−104.0 (3)
C19—C1—C2—C3	176.8 (3)	C6—C1—C19—C13	71.4 (3)
C1—C2—C3—C4	−0.4 (5)	C2—C1—C19—S1	137.6 (2)
C2—C3—C4—C5	0.2 (6)	C6—C1—C19—S1	−46.9 (3)
C3—C4—C5—C6	−0.9 (6)	C18—C13—C19—C7	−98.5 (3)
C4—C5—C6—C1	1.9 (6)	C14—C13—C19—C7	79.5 (4)
C2—C1—C6—C5	−2.0 (5)	C18—C13—C19—C1	25.2 (4)
C19—C1—C6—C5	−177.6 (3)	C14—C13—C19—C1	−156.8 (3)
C12—C7—C8—C9	0.3 (5)	C18—C13—C19—S1	138.2 (3)
C19—C7—C8—C9	178.6 (3)	C14—C13—C19—S1	−43.8 (4)
C7—C8—C9—C10	−0.9 (6)	C20—S1—C19—C7	−42.7 (2)
C8—C9—C10—C11	1.2 (6)	C20—S1—C19—C1	−160.5 (2)
C9—C10—C11—C12	−0.8 (6)	C20—S1—C19—C13	82.4 (2)
C10—C11—C12—C7	0.1 (6)	C19—S1—C20—C21	133.8 (3)
C8—C7—C12—C11	0.1 (5)	C22—O1—C21—C20	−157.3 (4)
C19—C7—C12—C11	−178.2 (3)	S1—C20—C21—O1	59.9 (4)
C18—C13—C14—C15	−0.8 (5)	C21—O1—C22—O2	−3.5 (7)
C19—C13—C14—C15	−178.9 (3)	C21—O1—C22—C23	175.9 (3)
C13—C14—C15—C16	0.1 (6)	O2—C22—C23—C24	−1.8 (7)
C14—C15—C16—C17	0.8 (6)	O1—C22—C23—C24	178.8 (4)
C15—C16—C17—C18	−1.0 (6)	O2—C22—C23—C28	178.7 (5)
C16—C17—C18—C13	0.2 (6)	O1—C22—C23—C28	−0.8 (6)
C14—C13—C18—C17	0.7 (5)	C28—C23—C24—C25	−0.6 (7)
C19—C13—C18—C17	178.7 (3)	C22—C23—C24—C25	179.8 (4)
C8—C7—C19—C1	−113.4 (3)	C23—C24—C25—C26	−0.1 (7)
C12—C7—C19—C1	64.9 (3)	C23—C24—C25—I1	177.1 (3)
C8—C7—C19—C13	9.6 (4)	C24—C25—C26—C27	0.7 (8)
C12—C7—C19—C13	−172.1 (3)	I1—C25—C26—C27	−176.5 (5)
C8—C7—C19—S1	133.9 (3)	C25—C26—C27—C28	−0.5 (10)
C12—C7—C19—S1	−47.8 (3)	C24—C23—C28—C27	0.8 (8)
C2—C1—C19—C7	20.8 (4)	C22—C23—C28—C27	−179.7 (5)
C6—C1—C19—C7	−163.8 (3)	C26—C27—C28—C23	−0.2 (9)

Experimental details

Crystal data
Chemical formula	C₂₈H₂₃IO₂S
M_r	550.42
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.1634 (8), 8.8413 (9), 18.9968 (18)
α, β, γ (°)	89.493 (1), 79.270 (2), 65.663 (1)
V (Å³)	1223.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.42
Crystal size (mm)	0.40 × 0.35 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS, Sheldrick, 1996)
T_min, T_max	0.601, 0.765
No. of measured, independent and observed [I > 2σ(I)] reflections	5948, 4254, 3375
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.126, 1.02
No. of reflections	4254
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.89, −1.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Henan University of Traditional Medicine and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, X., Lu, P. & Ng, S. W. (2011). Acta Cryst. E67, o2475. Web of Science CSD CrossRef IUCr Journals Google Scholar