2-(Tritylsulfan-yl)ethyl 2-iodo-benzoate.

The methine C atom of the triphenyl-methyl group in the title compound, C(28)H(23)IO(2)S, is slightly flattened out [ΣC(phen-yl)-C-C(phen-yl) = 335.6 (5)°]. The -C-O-C-C-S- chain connecting the triphenyl-methyl 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 = 550.42

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.096

S = 1.01

5564 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034180/xu5302sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811034180/xu5302Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H23IO2S	F(000) = 2208
Mr = 550.42	Dx = 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

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

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(Fo2) + (0.0525P)2 + 3.6231P] where P = (Fo2 + 2Fc2)/3
5564 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)