2-(Tritylsulfan­yl)ethyl 2-iodo­benzoate

Zhu, X.; Lu, P.; Ng, S.W.

doi:10.1107/S1600536811034180

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2475

doi:10.1107/S1600536811034180

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2-(Tritylsulfanyl)ethyl 2-iodobenzoate

Xin Zhu,^a Ping Lu ^a and Seik Weng Ng ^b,^c ^*

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

(Received 18 August 2011; accepted 20 August 2011; online 27 August 2011)

The methine C atom of the triphenylmethyl group in the title compound, C₂₈H₂₃IO₂S, is slightly flattened out [ΣC_phenyl—C—C_phenyl = 335.6 (5)°]. 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 = 0.120 Å).

Related literature

For the copper(I)-catalysed cleavage of S-tritylmethyl thioethers, see: Ma et al. (2007 ); Zhang et al. (2009 ).

Experimental

Crystal data

C₂₈H₂₃IO₂S
M_r = 550.42
Monoclinic, C 2/c
a = 28.4378 (4) Å
b = 9.6154 (1) Å
c = 18.3808 (2) Å
β = 106.618 (1)°
V = 4816.13 (10) Å³
Z = 8
Mo Kα radiation
μ = 1.44 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.672, T_max = 0.870
15633 measured reflections
5564 independent reflections
4506 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.096
S = 1.01
5564 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −0.34 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: 10.1107/S1600536811034180/xu5302sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034180/xu5302Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034180/xu5302Isup3.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 cupper(I) chloride-catalyzed cleavage investigation (Ma et al., 2007; Zhang et al., 2009). The methine carbon slightly flattened out (ΣC_phenyl–C–C_phenyl 335.6 (5) °) 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 0.120 Å) (Fig. 1).

Related literature top

For the copper(I)-catalysed cleavage of S-tritylmethyl thioethers, see: Ma et al. (2007); Zhang et al. (2009).

Experimental top

A solution of 2-iodobenzoic acid (1.24 g, 5 mmol), dicyclohexylcarbodiimide (1.65 g, 8 mmol) and 4-dimethylaminopyridine (0.98 g, 8 mmol) in THF (20 ml) was stirred for an hour. 2-(Tritylthio)ethanol (1.60 g, 5 mmol) was added. The reaction was stirred for 48 h. The compound was purified by column chromatography with petroleumether–chloroform (3:1) as the eluent. The compound was isolated upon evaporation of the solvent as yellow crystals (2.02 g, 70% yield).

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-[(triphenylmethyl)sulfanyl]ethyl 2-iodobenzoate top

Crystal data top

C₂₈H₂₃IO₂S	F(000) = 2208
M_r = 550.42	D_x = 1.518 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6921 reflections
a = 28.4378 (4) Å	θ = 2.4–27.4°
b = 9.6154 (1) Å	µ = 1.44 mm⁻¹
c = 18.3808 (2) Å	T = 293 K
β = 106.618 (1)°	Prism, yellow
V = 4816.13 (10) Å³	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	5564 independent reflections
Radiation source: fine-focus sealed tube	4506 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 27.7°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −37→33
T_min = 0.672, T_max = 0.870	k = −11→12
15633 measured reflections	l = −23→23

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0525P)² + 3.6231P] where P = (F_o² + 2F_c²)/3
5564 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.94 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₈H₂₃IO₂S	V = 4816.13 (10) Å³
M_r = 550.42	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.4378 (4) Å	µ = 1.44 mm⁻¹
b = 9.6154 (1) Å	T = 293 K
c = 18.3808 (2) Å	0.30 × 0.20 × 0.10 mm
β = 106.618 (1)°

Data collection top

Bruker SMART APEX diffractometer	5564 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4506 reflections with I > 2σ(I)
T_min = 0.672, T_max = 0.870	R_int = 0.017
15633 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.01	Δρ_max = 0.94 e Å⁻³
5564 reflections	Δρ_min = −0.34 e Å⁻³
289 parameters

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

	x	y	z	U_iso*/U_eq
I1	0.613888 (7)	0.54548 (2)	0.524788 (11)	0.06653 (9)
S1	0.42074 (2)	1.00910 (7)	0.68754 (4)	0.04999 (15)
O1	0.48562 (7)	0.6866 (2)	0.62115 (13)	0.0667 (5)
O2	0.56063 (9)	0.7361 (3)	0.6179 (2)	0.1131 (11)
C1	0.34622 (8)	1.1936 (2)	0.64315 (12)	0.0395 (4)
C2	0.36875 (10)	1.2693 (3)	0.70807 (14)	0.0538 (6)
H2	0.3901	1.2249	0.7494	0.065*
C3	0.35972 (11)	1.4105 (3)	0.71197 (17)	0.0653 (7)
H3	0.3759	1.4599	0.7554	0.078*
C4	0.32767 (12)	1.4781 (3)	0.65340 (18)	0.0632 (7)
H4	0.3219	1.5727	0.6566	0.076*
C5	0.30396 (11)	1.4042 (3)	0.58932 (16)	0.0581 (6)
H5	0.2814	1.4488	0.5494	0.070*
C6	0.31346 (9)	1.2644 (3)	0.58382 (13)	0.0477 (5)
H6	0.2977	1.2165	0.5396	0.057*
C7	0.34474 (8)	0.9869 (2)	0.55660 (12)	0.0378 (4)
C8	0.31287 (9)	0.8805 (3)	0.52546 (13)	0.0477 (5)
H8	0.2971	0.8321	0.5556	0.057*
C9	0.30400 (10)	0.8445 (3)	0.44904 (14)	0.0583 (6)
H9	0.2826	0.7721	0.4288	0.070*
C10	0.32654 (11)	0.9150 (3)	0.40389 (14)	0.0607 (7)
H10	0.3197	0.8927	0.3527	0.073*
C11	0.35946 (11)	1.0193 (3)	0.43456 (15)	0.0557 (6)
H11	0.3754	1.0662	0.4042	0.067*
C12	0.36889 (9)	1.0546 (2)	0.51009 (13)	0.0466 (5)
H12	0.3916	1.1242	0.5304	0.056*
C13	0.32141 (8)	0.9602 (2)	0.68042 (12)	0.0394 (4)
C14	0.33881 (9)	0.8611 (3)	0.73632 (13)	0.0485 (5)
H14	0.3721	0.8396	0.7514	0.058*
C15	0.30749 (11)	0.7933 (3)	0.77023 (14)	0.0563 (6)
H15	0.3199	0.7259	0.8070	0.068*
C16	0.25806 (10)	0.8250 (3)	0.74968 (14)	0.0562 (6)
H16	0.2371	0.7797	0.7724	0.067*
C17	0.24038 (10)	0.9249 (3)	0.69503 (15)	0.0532 (6)
H17	0.2072	0.9480	0.6812	0.064*
C18	0.27160 (9)	0.9912 (3)	0.66036 (13)	0.0467 (5)
H18	0.2590	1.0576	0.6231	0.056*
C19	0.35420 (8)	1.0362 (2)	0.63906 (12)	0.0385 (4)
C20	0.43229 (9)	0.8328 (3)	0.66178 (16)	0.0551 (6)
H20A	0.4385	0.7730	0.7060	0.066*
H20B	0.4037	0.7976	0.6236	0.066*
C21	0.47580 (10)	0.8317 (3)	0.63140 (17)	0.0601 (6)
H21A	0.4686	0.8811	0.5835	0.072*
H21B	0.5038	0.8752	0.6670	0.072*
C22	0.52920 (9)	0.6522 (3)	0.61484 (16)	0.0581 (6)
C23	0.53339 (9)	0.4982 (3)	0.60730 (14)	0.0515 (6)
C24	0.50377 (11)	0.4115 (4)	0.63571 (18)	0.0675 (7)
H24	0.4814	0.4507	0.6580	0.081*
C25	0.50676 (12)	0.2688 (4)	0.6317 (2)	0.0801 (9)
H25	0.4869	0.2125	0.6516	0.096*
C26	0.53938 (13)	0.2107 (4)	0.5980 (2)	0.0790 (9)
H26	0.5415	0.1145	0.5950	0.095*
C27	0.56871 (11)	0.2933 (3)	0.56890 (16)	0.0652 (7)
H27	0.5904	0.2527	0.5457	0.078*
C28	0.56646 (9)	0.4366 (3)	0.57364 (14)	0.0506 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.05710 (13)	0.06887 (15)	0.07605 (15)	0.00487 (8)	0.02295 (9)	0.00746 (9)
S1	0.0392 (3)	0.0480 (3)	0.0585 (3)	0.0024 (2)	0.0071 (2)	0.0001 (3)
O1	0.0485 (10)	0.0558 (11)	0.0997 (14)	0.0031 (9)	0.0275 (9)	−0.0087 (11)
O2	0.0711 (14)	0.0704 (16)	0.215 (3)	−0.0192 (13)	0.0685 (18)	−0.0479 (19)
C1	0.0402 (10)	0.0371 (11)	0.0428 (10)	−0.0014 (9)	0.0145 (8)	−0.0039 (9)
C2	0.0558 (14)	0.0530 (15)	0.0490 (12)	0.0005 (11)	0.0094 (10)	−0.0101 (11)
C3	0.0713 (17)	0.0556 (16)	0.0688 (16)	−0.0108 (14)	0.0200 (14)	−0.0277 (14)
C4	0.0789 (19)	0.0374 (14)	0.0806 (19)	0.0029 (13)	0.0346 (16)	−0.0084 (13)
C5	0.0715 (17)	0.0439 (14)	0.0613 (14)	0.0122 (13)	0.0226 (13)	0.0062 (12)
C6	0.0531 (13)	0.0414 (13)	0.0472 (11)	0.0047 (10)	0.0122 (10)	−0.0028 (10)
C7	0.0406 (10)	0.0333 (10)	0.0404 (10)	0.0039 (8)	0.0128 (8)	−0.0014 (8)
C8	0.0500 (12)	0.0442 (13)	0.0520 (12)	−0.0025 (10)	0.0197 (10)	−0.0074 (10)
C9	0.0576 (14)	0.0584 (16)	0.0587 (14)	−0.0045 (12)	0.0161 (11)	−0.0207 (13)
C10	0.0691 (16)	0.0694 (18)	0.0443 (12)	0.0090 (14)	0.0175 (11)	−0.0094 (12)
C11	0.0704 (16)	0.0532 (15)	0.0497 (13)	0.0091 (13)	0.0269 (12)	0.0060 (11)
C12	0.0542 (13)	0.0389 (12)	0.0489 (12)	0.0010 (10)	0.0184 (10)	0.0017 (10)
C13	0.0457 (11)	0.0358 (11)	0.0376 (10)	−0.0016 (9)	0.0133 (8)	−0.0049 (8)
C14	0.0562 (13)	0.0424 (13)	0.0471 (11)	0.0038 (11)	0.0152 (10)	0.0015 (10)
C15	0.0778 (17)	0.0461 (14)	0.0486 (12)	−0.0006 (13)	0.0238 (12)	0.0049 (11)
C16	0.0701 (16)	0.0510 (15)	0.0561 (13)	−0.0126 (13)	0.0315 (12)	−0.0054 (12)
C17	0.0498 (13)	0.0575 (15)	0.0570 (13)	−0.0053 (11)	0.0228 (11)	−0.0069 (12)
C18	0.0483 (12)	0.0465 (13)	0.0456 (11)	0.0010 (10)	0.0141 (10)	0.0020 (10)
C19	0.0377 (10)	0.0362 (11)	0.0406 (10)	0.0010 (8)	0.0098 (8)	0.0012 (8)
C20	0.0473 (13)	0.0479 (14)	0.0692 (15)	0.0100 (11)	0.0154 (11)	0.0047 (12)
C21	0.0527 (14)	0.0559 (16)	0.0718 (16)	0.0020 (12)	0.0181 (12)	−0.0063 (13)
C22	0.0429 (12)	0.0636 (17)	0.0682 (15)	−0.0021 (12)	0.0164 (11)	−0.0129 (13)
C23	0.0399 (12)	0.0550 (14)	0.0537 (13)	0.0027 (11)	0.0038 (10)	−0.0012 (12)
C24	0.0514 (14)	0.0707 (19)	0.0801 (19)	0.0011 (14)	0.0182 (13)	0.0079 (16)
C25	0.0674 (19)	0.072 (2)	0.098 (2)	−0.0073 (17)	0.0195 (17)	0.0247 (19)
C26	0.083 (2)	0.0524 (18)	0.095 (2)	0.0014 (16)	0.0163 (18)	0.0085 (17)
C27	0.0673 (17)	0.0558 (17)	0.0693 (16)	0.0127 (14)	0.0146 (13)	0.0021 (14)
C28	0.0438 (12)	0.0512 (14)	0.0512 (12)	0.0043 (10)	0.0048 (10)	0.0019 (11)

Geometric parameters (Å, º) top

I1—C28	2.101 (3)	C12—H12	0.9300
S1—C20	1.815 (3)	C13—C14	1.385 (3)
S1—C19	1.865 (2)	C13—C18	1.390 (3)
O1—C22	1.319 (3)	C13—C19	1.544 (3)
O1—C21	1.445 (4)	C14—C15	1.387 (4)
O2—C22	1.193 (4)	C14—H14	0.9300
C1—C2	1.388 (3)	C15—C16	1.381 (4)
C1—C6	1.392 (3)	C15—H15	0.9300
C1—C19	1.536 (3)	C16—C17	1.376 (4)
C2—C3	1.387 (4)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.388 (4)
C3—C4	1.360 (5)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.375 (4)	C20—C21	1.496 (4)
C4—H4	0.9300	C20—H20A	0.9700
C5—C6	1.381 (4)	C20—H20B	0.9700
C5—H5	0.9300	C21—H21A	0.9700
C6—H6	0.9300	C21—H21B	0.9700
C7—C8	1.378 (3)	C22—C23	1.495 (4)
C7—C12	1.401 (3)	C23—C24	1.389 (4)
C7—C19	1.537 (3)	C23—C28	1.397 (4)
C8—C9	1.398 (3)	C24—C25	1.378 (5)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.365 (4)	C25—C26	1.373 (5)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.378 (4)	C26—C27	1.366 (5)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.379 (3)	C27—C28	1.383 (4)
C11—H11	0.9300	C27—H27	0.9300

C20—S1—C19	103.90 (11)	C17—C16—H16	120.5
C22—O1—C21	118.3 (2)	C15—C16—H16	120.5
C2—C1—C6	117.3 (2)	C16—C17—C18	120.5 (2)
C2—C1—C19	121.4 (2)	C16—C17—H17	119.7
C6—C1—C19	121.23 (19)	C18—C17—H17	119.7
C3—C2—C1	120.7 (2)	C17—C18—C13	121.1 (2)
C3—C2—H2	119.6	C17—C18—H18	119.4
C1—C2—H2	119.6	C13—C18—H18	119.4
C4—C3—C2	121.2 (3)	C1—C19—C7	111.43 (17)
C4—C3—H3	119.4	C1—C19—C13	108.88 (17)
C2—C3—H3	119.4	C7—C19—C13	112.31 (17)
C3—C4—C5	119.0 (3)	C1—C19—S1	104.96 (14)
C3—C4—H4	120.5	C7—C19—S1	107.20 (14)
C5—C4—H4	120.5	C13—C19—S1	111.83 (14)
C4—C5—C6	120.5 (3)	C21—C20—S1	109.6 (2)
C4—C5—H5	119.8	C21—C20—H20A	109.8
C6—C5—H5	119.8	S1—C20—H20A	109.8
C5—C6—C1	121.3 (2)	C21—C20—H20B	109.8
C5—C6—H6	119.3	S1—C20—H20B	109.8
C1—C6—H6	119.3	H20A—C20—H20B	108.2
C8—C7—C12	118.1 (2)	O1—C21—C20	105.5 (2)
C8—C7—C19	123.2 (2)	O1—C21—H21A	110.6
C12—C7—C19	118.7 (2)	C20—C21—H21A	110.6
C7—C8—C9	120.6 (2)	O1—C21—H21B	110.6
C7—C8—H8	119.7	C20—C21—H21B	110.6
C9—C8—H8	119.7	H21A—C21—H21B	108.8
C10—C9—C8	120.5 (3)	O2—C22—O1	122.4 (3)
C10—C9—H9	119.8	O2—C22—C23	126.5 (3)
C8—C9—H9	119.8	O1—C22—C23	111.0 (2)
C9—C10—C11	119.7 (2)	C24—C23—C28	118.0 (3)
C9—C10—H10	120.2	C24—C23—C22	119.1 (3)
C11—C10—H10	120.2	C28—C23—C22	122.9 (2)
C10—C11—C12	120.3 (2)	C25—C24—C23	121.7 (3)
C10—C11—H11	119.8	C25—C24—H24	119.2
C12—C11—H11	119.8	C23—C24—H24	119.2
C11—C12—C7	120.8 (2)	C26—C25—C24	119.3 (3)
C11—C12—H12	119.6	C26—C25—H25	120.4
C7—C12—H12	119.6	C24—C25—H25	120.4
C14—C13—C18	117.7 (2)	C27—C26—C25	120.5 (3)
C14—C13—C19	123.5 (2)	C27—C26—H26	119.8
C18—C13—C19	118.74 (19)	C25—C26—H26	119.8
C13—C14—C15	121.2 (2)	C26—C27—C28	120.6 (3)
C13—C14—H14	119.4	C26—C27—H27	119.7
C15—C14—H14	119.4	C28—C27—H27	119.7
C16—C15—C14	120.5 (2)	C27—C28—C23	120.0 (3)
C16—C15—H15	119.8	C27—C28—I1	115.0 (2)
C14—C15—H15	119.8	C23—C28—I1	125.0 (2)
C17—C16—C15	119.0 (2)

C6—C1—C2—C3	−1.9 (4)	C12—C7—C19—C13	174.8 (2)
C19—C1—C2—C3	−177.5 (2)	C8—C7—C19—S1	119.2 (2)
C1—C2—C3—C4	1.8 (5)	C12—C7—C19—S1	−62.0 (2)
C2—C3—C4—C5	0.0 (5)	C14—C13—C19—C1	−128.4 (2)
C3—C4—C5—C6	−1.6 (4)	C18—C13—C19—C1	52.3 (3)
C4—C5—C6—C1	1.5 (4)	C14—C13—C19—C7	107.7 (2)
C2—C1—C6—C5	0.3 (4)	C18—C13—C19—C7	−71.6 (3)
C19—C1—C6—C5	175.9 (2)	C14—C13—C19—S1	−12.9 (3)
C12—C7—C8—C9	−1.9 (4)	C18—C13—C19—S1	167.80 (17)
C19—C7—C8—C9	177.0 (2)	C20—S1—C19—C1	−166.42 (15)
C7—C8—C9—C10	−0.4 (4)	C20—S1—C19—C7	−47.83 (17)
C8—C9—C10—C11	2.1 (4)	C20—S1—C19—C13	75.69 (17)
C9—C10—C11—C12	−1.3 (4)	C19—S1—C20—C21	129.09 (19)
C10—C11—C12—C7	−1.0 (4)	C22—O1—C21—C20	−161.8 (2)
C8—C7—C12—C11	2.6 (3)	S1—C20—C21—O1	173.37 (18)
C19—C7—C12—C11	−176.3 (2)	C21—O1—C22—O2	0.6 (5)
C18—C13—C14—C15	1.1 (3)	C21—O1—C22—C23	178.1 (2)
C19—C13—C14—C15	−178.2 (2)	O2—C22—C23—C24	153.0 (4)
C13—C14—C15—C16	−1.1 (4)	O1—C22—C23—C24	−24.4 (4)
C14—C15—C16—C17	0.1 (4)	O2—C22—C23—C28	−26.1 (5)
C15—C16—C17—C18	0.9 (4)	O1—C22—C23—C28	156.5 (2)
C16—C17—C18—C13	−0.8 (4)	C28—C23—C24—C25	0.5 (4)
C14—C13—C18—C17	−0.2 (3)	C22—C23—C24—C25	−178.7 (3)
C19—C13—C18—C17	179.2 (2)	C23—C24—C25—C26	−0.8 (5)
C2—C1—C19—C7	−156.2 (2)	C24—C25—C26—C27	0.2 (5)
C6—C1—C19—C7	28.3 (3)	C25—C26—C27—C28	0.8 (5)
C2—C1—C19—C13	79.4 (3)	C26—C27—C28—C23	−1.1 (4)
C6—C1—C19—C13	−96.1 (2)	C26—C27—C28—I1	−179.5 (2)
C2—C1—C19—S1	−40.5 (3)	C24—C23—C28—C27	0.5 (4)
C6—C1—C19—S1	144.05 (18)	C22—C23—C28—C27	179.6 (2)
C8—C7—C19—C1	−126.5 (2)	C24—C23—C28—I1	178.69 (19)
C12—C7—C19—C1	52.3 (3)	C22—C23—C28—I1	−2.2 (3)
C8—C7—C19—C13	−4.0 (3)

Experimental details

Crystal data
Chemical formula	C₂₈H₂₃IO₂S
M_r	550.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	28.4378 (4), 9.6154 (1), 18.3808 (2)
β (°)	106.618 (1)
V (Å³)	4816.13 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.44
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.672, 0.870
No. of measured, independent and observed [I > 2σ(I)] reflections	15633, 5564, 4506
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.096, 1.01
No. of reflections	5564
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.94, −0.34

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

Acknowledgements

The authors 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
Ma, M., Zhang, X., Peng, L. & Wang, J. (2007). Tetrahedron Lett. 48, 1095–1097. CrossRef CAS 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
Zhang, Y.-Z., Zhu, X.-F., Cai, Y., Mao, H.-X. & Zhou, Q.-L. (2009). Chem. Commun. pp. 5362–5364. CrossRef Google Scholar