3-Cyclo-hexyl-sulfinyl-5-iodo-2-methyl-1-benzofuran.

There are two independent mol-ecules, A and B, in the asymmetric unit of the title compound, C(15)H(17)ClO(2)S, in each of which the cyclo-hexyl ring adopts a chair conformation. The benzofuran units in each mol-ecule are essentially planar, with mean deviations from a least-squares plane defined by the nine constituent ring atoms of 0.006 (2) Å for A and 0.011 (2) Å for B. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions and by two I⋯O contacts [I⋯O = 3.079 (2) and 3.017 (2) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of the related 5-bromo-3-cyclo­hexyl­sulfinyl-2-methyl-1-benzofuran, see: Choi et al. (2011 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C15H17IO2S

M = 388.25

Monoclinic,

a = 14.1817 (2) Å

b = 12.1347 (2) Å

c = 18.1258 (3) Å

β = 101.136 (1)°

V = 3060.55 (8) Å3

Z = 8

Mo Kα radiation

μ = 2.22 mm−1

T = 173 K

0.20 × 0.17 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.663, T max = 0.758

30319 measured reflections

7599 independent reflections

6386 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.04

7599 reflections

345 parameters

H-atom parameters constrained

Δρmax = 2.47 e Å−3

Δρmin = −1.61 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101124X/nk2093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101124X/nk2093Isup2.hkl

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

C15H17IO2S	F(000) = 1536
Mr = 388.25	Dx = 1.685 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9976 reflections
a = 14.1817 (2) Å	θ = 2.3–28.2°
b = 12.1347 (2) Å	µ = 2.22 mm−1
c = 18.1258 (3) Å	T = 173 K
β = 101.136 (1)°	Block, colourless
V = 3060.55 (8) Å3	0.20 × 0.17 × 0.13 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	7599 independent reflections
Radiation source: rotating anode	6386 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.7°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→16
Tmin = 0.663, Tmax = 0.758	l = −24→23
30319 measured reflections

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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F2) = 0.077	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0307P)2 + 3.4955P] where P = (Fo2 + 2Fc2)/3
7599 reflections	(Δ/σ)max = 0.001
345 parameters	Δρmax = 2.47 e Å−3
0 restraints	Δρmin = −1.61 e Å−3

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.

	x	y	z	Uiso*/Ueq
I1	1.048528 (14)	0.580334 (16)	0.151097 (11)	0.03378 (6)
I2	0.606210 (13)	0.569038 (16)	0.364814 (11)	0.03435 (6)
S1	0.72639 (5)	0.32745 (6)	0.29877 (4)	0.02762 (14)
S2	0.22444 (5)	0.80407 (6)	0.18499 (4)	0.02861 (15)
O1	0.68592 (14)	0.28895 (17)	0.07955 (10)	0.0312 (4)
O2	0.77106 (16)	0.43298 (16)	0.33139 (12)	0.0354 (5)
O3	0.26297 (14)	0.86421 (16)	0.40235 (11)	0.0322 (4)
O4	0.24814 (16)	0.68779 (16)	0.16682 (12)	0.0369 (5)
C1	0.73199 (18)	0.3275 (2)	0.20232 (15)	0.0263 (5)
C2	0.79737 (18)	0.3824 (2)	0.16304 (14)	0.0237 (5)
C3	0.87765 (19)	0.4506 (2)	0.18295 (15)	0.0260 (5)
H3	0.9009	0.4713	0.2338	0.031*
C4	0.9221 (2)	0.4868 (2)	0.12557 (16)	0.0286 (6)
C5	0.8874 (2)	0.4594 (2)	0.05048 (15)	0.0298 (6)
H5	0.9193	0.4868	0.0128	0.036*
C6	0.8072 (2)	0.3928 (2)	0.02990 (15)	0.0294 (6)
H6	0.7826	0.3741	−0.0211	0.035*
C7	0.76537 (18)	0.3556 (2)	0.08750 (15)	0.0260 (5)
C8	0.6672 (2)	0.2731 (2)	0.15035 (16)	0.0306 (6)
C9	0.5859 (2)	0.1992 (3)	0.15600 (18)	0.0457 (8)
H9A	0.6053	0.1224	0.1510	0.069*
H9B	0.5311	0.2167	0.1158	0.069*
H9C	0.5675	0.2094	0.2049	0.069*
C10	0.81125 (18)	0.2169 (2)	0.33125 (14)	0.0255 (5)
H10	0.7934	0.1514	0.2980	0.031*
C11	0.91371 (19)	0.2497 (2)	0.32762 (17)	0.0304 (6)
H11A	0.9293	0.3207	0.3540	0.037*
H11B	0.9194	0.2599	0.2745	0.037*
C12	0.9852 (2)	0.1619 (3)	0.36373 (17)	0.0357 (7)
H12A	0.9738	0.0929	0.3343	0.043*
H12B	1.0515	0.1870	0.3631	0.043*
C13	0.9748 (2)	0.1400 (3)	0.44408 (17)	0.0392 (7)
H13A	1.0215	0.0827	0.4664	0.047*
H13B	0.9890	0.2081	0.4742	0.047*
C14	0.8737 (2)	0.1017 (3)	0.44614 (18)	0.0404 (7)
H14A	0.8677	0.0887	0.4990	0.048*
H14B	0.8612	0.0311	0.4186	0.048*
C15	0.7997 (2)	0.1864 (3)	0.41089 (15)	0.0325 (6)
H15A	0.8066	0.2536	0.4425	0.039*
H15B	0.7344	0.1564	0.4092	0.039*
C16	0.26577 (18)	0.8201 (2)	0.28238 (15)	0.0253 (5)
C17	0.34816 (19)	0.7692 (2)	0.32891 (15)	0.0246 (5)
C18	0.42387 (18)	0.7019 (2)	0.31737 (15)	0.0254 (5)
H18	0.4301	0.6803	0.2682	0.031*
C19	0.48971 (19)	0.6675 (2)	0.38001 (16)	0.0284 (6)
C20	0.4808 (2)	0.6979 (3)	0.45277 (17)	0.0369 (7)
H20	0.5269	0.6728	0.4946	0.044*
C21	0.4057 (2)	0.7641 (3)	0.46466 (17)	0.0362 (7)
H21	0.3986	0.7846	0.5139	0.043*
C22	0.34195 (19)	0.7987 (2)	0.40232 (16)	0.0283 (6)
C23	0.2177 (2)	0.8744 (2)	0.32817 (16)	0.0296 (6)
C24	0.1296 (2)	0.9429 (3)	0.3152 (2)	0.0410 (7)
H24A	0.1470	1.0204	0.3248	0.061*
H24B	0.0875	0.9192	0.3492	0.061*
H24C	0.0958	0.9343	0.2630	0.061*
C25	0.30894 (19)	0.8935 (2)	0.15006 (15)	0.0256 (5)
H25	0.3751	0.8806	0.1798	0.031*
C26	0.3067 (2)	0.8650 (3)	0.06778 (16)	0.0383 (7)
H26A	0.3276	0.7877	0.0638	0.046*
H26B	0.2403	0.8720	0.0389	0.046*
C27	0.3730 (3)	0.9418 (3)	0.03484 (19)	0.0445 (8)
H27A	0.4404	0.9276	0.0596	0.053*
H27B	0.3670	0.9261	−0.0195	0.053*
C28	0.3495 (3)	1.0609 (3)	0.04503 (18)	0.0402 (7)
H28A	0.2855	1.0779	0.0143	0.048*
H28B	0.3975	1.1080	0.0271	0.048*
C29	0.3492 (2)	1.0873 (2)	0.12676 (18)	0.0355 (7)
H29A	0.3300	1.1651	0.1310	0.043*
H29B	0.4150	1.0782	0.1566	0.043*
C30	0.2808 (2)	1.0129 (2)	0.15881 (17)	0.0305 (6)
H30A	0.2841	1.0301	0.2126	0.037*
H30B	0.2140	1.0254	0.1318	0.037*

	U11	U22	U33	U12	U13	U23
I1	0.03315 (11)	0.03675 (11)	0.03020 (10)	−0.01283 (8)	0.00306 (8)	−0.00015 (7)
I2	0.02812 (10)	0.03482 (11)	0.03866 (12)	0.00881 (7)	0.00288 (8)	−0.00231 (8)
S1	0.0232 (3)	0.0339 (3)	0.0270 (3)	0.0034 (3)	0.0080 (3)	−0.0011 (3)
S2	0.0251 (3)	0.0257 (3)	0.0328 (4)	−0.0052 (3)	0.0000 (3)	0.0027 (3)
O1	0.0288 (10)	0.0386 (11)	0.0257 (10)	−0.0108 (9)	0.0037 (8)	−0.0012 (8)
O2	0.0373 (12)	0.0329 (11)	0.0360 (11)	0.0062 (9)	0.0073 (9)	−0.0083 (9)
O3	0.0322 (10)	0.0312 (10)	0.0351 (11)	0.0073 (8)	0.0114 (9)	−0.0012 (9)
O4	0.0462 (12)	0.0228 (9)	0.0396 (12)	−0.0084 (9)	0.0032 (10)	−0.0031 (9)
C1	0.0226 (12)	0.0303 (13)	0.0254 (13)	0.0017 (11)	0.0033 (10)	0.0015 (11)
C2	0.0232 (12)	0.0237 (12)	0.0231 (12)	0.0029 (10)	0.0022 (10)	0.0005 (10)
C3	0.0281 (13)	0.0259 (13)	0.0233 (13)	0.0004 (11)	0.0031 (10)	−0.0013 (10)
C4	0.0275 (14)	0.0271 (13)	0.0310 (14)	−0.0040 (11)	0.0051 (11)	−0.0006 (11)
C5	0.0316 (14)	0.0345 (14)	0.0249 (13)	−0.0048 (12)	0.0092 (11)	0.0016 (11)
C6	0.0329 (15)	0.0324 (14)	0.0215 (13)	−0.0031 (12)	0.0016 (11)	−0.0016 (11)
C7	0.0221 (12)	0.0262 (13)	0.0278 (13)	−0.0030 (10)	0.0003 (10)	−0.0014 (11)
C8	0.0248 (13)	0.0368 (15)	0.0294 (14)	−0.0021 (12)	0.0034 (11)	0.0015 (12)
C9	0.0363 (17)	0.062 (2)	0.0374 (17)	−0.0221 (16)	0.0049 (14)	−0.0019 (16)
C10	0.0257 (13)	0.0273 (13)	0.0236 (12)	0.0010 (11)	0.0055 (10)	−0.0018 (10)
C11	0.0253 (13)	0.0341 (15)	0.0341 (15)	0.0047 (11)	0.0109 (11)	0.0094 (12)
C12	0.0300 (15)	0.0400 (16)	0.0381 (16)	0.0094 (13)	0.0085 (12)	0.0099 (13)
C13	0.0383 (17)	0.0414 (17)	0.0345 (16)	0.0015 (14)	−0.0019 (13)	0.0096 (14)
C14	0.0417 (18)	0.0476 (18)	0.0320 (16)	−0.0045 (15)	0.0071 (13)	0.0136 (14)
C15	0.0327 (15)	0.0411 (16)	0.0250 (13)	−0.0029 (13)	0.0089 (11)	0.0023 (12)
C16	0.0219 (12)	0.0233 (12)	0.0310 (14)	−0.0013 (10)	0.0058 (10)	0.0038 (11)
C17	0.0256 (13)	0.0216 (12)	0.0270 (13)	−0.0022 (10)	0.0059 (10)	0.0018 (10)
C18	0.0255 (13)	0.0260 (13)	0.0252 (13)	−0.0007 (10)	0.0060 (10)	−0.0016 (10)
C19	0.0243 (13)	0.0265 (13)	0.0341 (15)	0.0020 (11)	0.0049 (11)	−0.0024 (11)
C20	0.0354 (16)	0.0410 (17)	0.0314 (15)	0.0078 (13)	−0.0011 (12)	−0.0016 (13)
C21	0.0405 (17)	0.0422 (17)	0.0269 (14)	0.0037 (14)	0.0087 (12)	−0.0050 (12)
C22	0.0278 (13)	0.0266 (13)	0.0319 (14)	0.0030 (11)	0.0096 (11)	−0.0012 (11)
C23	0.0266 (13)	0.0255 (13)	0.0375 (15)	0.0005 (11)	0.0083 (12)	0.0022 (12)
C24	0.0331 (16)	0.0384 (17)	0.053 (2)	0.0119 (13)	0.0122 (15)	0.0045 (15)
C25	0.0258 (13)	0.0245 (12)	0.0256 (13)	−0.0034 (10)	0.0025 (10)	0.0017 (10)
C26	0.0544 (19)	0.0330 (15)	0.0278 (14)	−0.0071 (14)	0.0084 (13)	−0.0033 (12)
C27	0.064 (2)	0.0417 (18)	0.0322 (16)	−0.0072 (16)	0.0209 (16)	−0.0020 (14)
C28	0.0455 (19)	0.0386 (17)	0.0354 (16)	−0.0054 (14)	0.0051 (14)	0.0108 (13)
C29	0.0391 (17)	0.0233 (13)	0.0462 (18)	−0.0038 (12)	0.0133 (14)	−0.0001 (12)
C30	0.0299 (14)	0.0236 (13)	0.0382 (15)	−0.0021 (11)	0.0074 (12)	0.0001 (11)

I1—C4	2.097 (3)	C13—H13A	0.9900
I1—O4i	3.079 (2)	C13—H13B	0.9900
I2—C19	2.100 (3)	C14—C15	1.520 (4)
I2—O2	3.017 (2)	C14—H14A	0.9900
S1—O2	1.499 (2)	C14—H14B	0.9900
S1—C1	1.765 (3)	C15—H15A	0.9900
S1—C10	1.822 (3)	C15—H15B	0.9900
S2—O4	1.502 (2)	C16—C23	1.344 (4)
S2—C16	1.760 (3)	C16—C17	1.441 (4)
S2—C25	1.819 (3)	C17—C18	1.397 (4)
O1—C7	1.372 (3)	C17—C22	1.397 (4)
O1—C8	1.373 (3)	C18—C19	1.387 (4)
O3—C22	1.373 (3)	C18—H18	0.9500
O3—C23	1.379 (3)	C19—C20	1.398 (4)
C1—C8	1.354 (4)	C20—C21	1.383 (4)
C1—C2	1.438 (4)	C20—H20	0.9500
C2—C7	1.395 (4)	C21—C22	1.370 (4)
C2—C3	1.397 (4)	C21—H21	0.9500
C3—C4	1.388 (4)	C23—C24	1.481 (4)
C3—H3	0.9500	C24—H24A	0.9800
C4—C5	1.395 (4)	C24—H24B	0.9800
C5—C6	1.386 (4)	C24—H24C	0.9800
C5—H5	0.9500	C25—C30	1.520 (4)
C6—C7	1.373 (4)	C25—C26	1.525 (4)
C6—H6	0.9500	C25—H25	1.0000
C8—C9	1.480 (4)	C26—C27	1.525 (4)
C9—H9A	0.9800	C26—H26A	0.9900
C9—H9B	0.9800	C26—H26B	0.9900
C9—H9C	0.9800	C27—C28	1.503 (5)
C10—C11	1.520 (4)	C27—H27A	0.9900
C10—C15	1.530 (4)	C27—H27B	0.9900
C10—H10	1.0000	C28—C29	1.516 (4)
C11—C12	1.528 (4)	C28—H28A	0.9900
C11—H11A	0.9900	C28—H28B	0.9900
C11—H11B	0.9900	C29—C30	1.520 (4)
C12—C13	1.515 (4)	C29—H29A	0.9900
C12—H12A	0.9900	C29—H29B	0.9900
C12—H12B	0.9900	C30—H30A	0.9900
C13—C14	1.515 (4)	C30—H30B	0.9900
C4—I1—O4i	168.88 (9)	C14—C15—H15A	109.3
C19—I2—O2	175.89 (9)	C10—C15—H15A	109.3
O2—S1—C1	107.12 (13)	C14—C15—H15B	109.3
O2—S1—C10	107.39 (12)	C10—C15—H15B	109.3
C1—S1—C10	99.60 (12)	H15A—C15—H15B	108.0
O4—S2—C16	106.17 (12)	C23—C16—C17	107.4 (2)
O4—S2—C25	107.09 (13)	C23—C16—S2	124.3 (2)
C16—S2—C25	99.73 (12)	C17—C16—S2	127.9 (2)
C7—O1—C8	106.7 (2)	C18—C17—C22	119.0 (2)
S1—O2—I2	105.19 (10)	C18—C17—C16	136.3 (2)
C22—O3—C23	106.1 (2)	C22—C17—C16	104.7 (2)
C8—C1—C2	107.3 (2)	C19—C18—C17	117.9 (2)
C8—C1—S1	122.3 (2)	C19—C18—H18	121.0
C2—C1—S1	130.3 (2)	C17—C18—H18	121.0
C7—C2—C3	119.1 (2)	C18—C19—C20	121.5 (3)
C7—C2—C1	105.0 (2)	C18—C19—I2	119.1 (2)
C3—C2—C1	135.9 (2)	C20—C19—I2	119.4 (2)
C4—C3—C2	117.3 (2)	C21—C20—C19	120.8 (3)
C4—C3—H3	121.3	C21—C20—H20	119.6
C2—C3—H3	121.3	C19—C20—H20	119.6
C3—C4—C5	122.0 (3)	C22—C21—C20	117.1 (3)
C3—C4—I1	119.9 (2)	C22—C21—H21	121.5
C5—C4—I1	118.0 (2)	C20—C21—H21	121.5
C6—C5—C4	121.2 (3)	C21—C22—O3	125.8 (3)
C6—C5—H5	119.4	C21—C22—C17	123.6 (3)
C4—C5—H5	119.4	O3—C22—C17	110.5 (2)
C7—C6—C5	116.1 (2)	C16—C23—O3	111.2 (2)
C7—C6—H6	122.0	C16—C23—C24	133.6 (3)
C5—C6—H6	122.0	O3—C23—C24	115.1 (3)
O1—C7—C6	125.5 (2)	C23—C24—H24A	109.5
O1—C7—C2	110.2 (2)	C23—C24—H24B	109.5
C6—C7—C2	124.2 (2)	H24A—C24—H24B	109.5
C1—C8—O1	110.8 (2)	C23—C24—H24C	109.5
C1—C8—C9	132.9 (3)	H24A—C24—H24C	109.5
O1—C8—C9	116.3 (2)	H24B—C24—H24C	109.5
C8—C9—H9A	109.5	C30—C25—C26	111.2 (2)
C8—C9—H9B	109.5	C30—C25—S2	109.18 (19)
H9A—C9—H9B	109.5	C26—C25—S2	108.34 (19)
C8—C9—H9C	109.5	C30—C25—H25	109.4
H9A—C9—H9C	109.5	C26—C25—H25	109.4
H9B—C9—H9C	109.5	S2—C25—H25	109.4
C11—C10—C15	112.5 (2)	C27—C26—C25	110.3 (2)
C11—C10—S1	111.76 (19)	C27—C26—H26A	109.6
C15—C10—S1	107.37 (18)	C25—C26—H26A	109.6
C11—C10—H10	108.4	C27—C26—H26B	109.6
C15—C10—H10	108.4	C25—C26—H26B	109.6
S1—C10—H10	108.4	H26A—C26—H26B	108.1
C10—C11—C12	111.1 (2)	C28—C27—C26	111.8 (3)
C10—C11—H11A	109.4	C28—C27—H27A	109.2
C12—C11—H11A	109.4	C26—C27—H27A	109.2
C10—C11—H11B	109.4	C28—C27—H27B	109.2
C12—C11—H11B	109.4	C26—C27—H27B	109.2
H11A—C11—H11B	108.0	H27A—C27—H27B	107.9
C13—C12—C11	110.8 (2)	C27—C28—C29	111.4 (3)
C13—C12—H12A	109.5	C27—C28—H28A	109.3
C11—C12—H12A	109.5	C29—C28—H28A	109.3
C13—C12—H12B	109.5	C27—C28—H28B	109.3
C11—C12—H12B	109.5	C29—C28—H28B	109.3
H12A—C12—H12B	108.1	H28A—C28—H28B	108.0
C14—C13—C12	110.2 (3)	C28—C29—C30	111.8 (3)
C14—C13—H13A	109.6	C28—C29—H29A	109.3
C12—C13—H13A	109.6	C30—C29—H29A	109.3
C14—C13—H13B	109.6	C28—C29—H29B	109.3
C12—C13—H13B	109.6	C30—C29—H29B	109.3
H13A—C13—H13B	108.1	H29A—C29—H29B	107.9
C13—C14—C15	111.3 (3)	C25—C30—C29	109.0 (2)
C13—C14—H14A	109.4	C25—C30—H30A	109.9
C15—C14—H14A	109.4	C29—C30—H30A	109.9
C13—C14—H14B	109.4	C25—C30—H30B	109.9
C15—C14—H14B	109.4	C29—C30—H30B	109.9
H14A—C14—H14B	108.0	H30A—C30—H30B	108.3
C14—C15—C10	111.7 (2)
C1—S1—O2—I2	109.41 (11)	C11—C10—C15—C14	−51.5 (3)
C10—S1—O2—I2	−144.37 (10)	S1—C10—C15—C14	−174.9 (2)
O2—S1—C1—C8	−151.8 (2)	O4—S2—C16—C23	−139.2 (2)
C10—S1—C1—C8	96.5 (3)	C25—S2—C16—C23	109.7 (2)
O2—S1—C1—C2	25.9 (3)	O4—S2—C16—C17	32.9 (3)
C10—S1—C1—C2	−85.8 (3)	C25—S2—C16—C17	−78.2 (3)
C8—C1—C2—C7	0.0 (3)	C23—C16—C17—C18	178.7 (3)
S1—C1—C2—C7	−178.0 (2)	S2—C16—C17—C18	5.5 (5)
C8—C1—C2—C3	179.6 (3)	C23—C16—C17—C22	0.1 (3)
S1—C1—C2—C3	1.6 (5)	S2—C16—C17—C22	−173.1 (2)
C7—C2—C3—C4	−0.8 (4)	C22—C17—C18—C19	−0.1 (4)
C1—C2—C3—C4	179.6 (3)	C16—C17—C18—C19	−178.5 (3)
C2—C3—C4—C5	1.6 (4)	C17—C18—C19—C20	0.6 (4)
C2—C3—C4—I1	−175.79 (19)	C17—C18—C19—I2	−178.69 (19)
O4i—I1—C4—C3	134.7 (4)	C18—C19—C20—C21	−0.3 (5)
O4i—I1—C4—C5	−42.8 (6)	I2—C19—C20—C21	179.0 (2)
C3—C4—C5—C6	−1.0 (5)	C19—C20—C21—C22	−0.6 (5)
I1—C4—C5—C6	176.5 (2)	C20—C21—C22—O3	179.8 (3)
C4—C5—C6—C7	−0.5 (4)	C20—C21—C22—C17	1.2 (5)
C8—O1—C7—C6	−179.0 (3)	C23—O3—C22—C21	−177.6 (3)
C8—O1—C7—C2	−0.1 (3)	C23—O3—C22—C17	1.1 (3)
C5—C6—C7—O1	−179.9 (3)	C18—C17—C22—C21	−0.9 (4)
C5—C6—C7—C2	1.4 (4)	C16—C17—C22—C21	178.0 (3)
C3—C2—C7—O1	−179.6 (2)	C18—C17—C22—O3	−179.6 (2)
C1—C2—C7—O1	0.1 (3)	C16—C17—C22—O3	−0.8 (3)
C3—C2—C7—C6	−0.7 (4)	C17—C16—C23—O3	0.6 (3)
C1—C2—C7—C6	179.0 (3)	S2—C16—C23—O3	174.09 (19)
C2—C1—C8—O1	0.0 (3)	C17—C16—C23—C24	179.2 (3)
S1—C1—C8—O1	178.18 (19)	S2—C16—C23—C24	−7.3 (5)
C2—C1—C8—C9	177.0 (3)	C22—O3—C23—C16	−1.1 (3)
S1—C1—C8—C9	−4.8 (5)	C22—O3—C23—C24	−179.9 (2)
C7—O1—C8—C1	0.0 (3)	O4—S2—C25—C30	173.43 (18)
C7—O1—C8—C9	−177.5 (3)	C16—S2—C25—C30	−76.2 (2)
O2—S1—C10—C11	−42.6 (2)	O4—S2—C25—C26	52.1 (2)
C1—S1—C10—C11	68.8 (2)	C16—S2—C25—C26	162.5 (2)
O2—S1—C10—C15	81.1 (2)	C30—C25—C26—C27	57.2 (3)
C1—S1—C10—C15	−167.41 (19)	S2—C25—C26—C27	177.2 (2)
C15—C10—C11—C12	52.3 (3)	C25—C26—C27—C28	−54.6 (4)
S1—C10—C11—C12	173.2 (2)	C26—C27—C28—C29	54.0 (4)
C10—C11—C12—C13	−56.1 (3)	C27—C28—C29—C30	−55.8 (4)
C11—C12—C13—C14	59.0 (4)	C26—C25—C30—C29	−58.3 (3)
C12—C13—C14—C15	−58.2 (4)	S2—C25—C30—C29	−177.8 (2)
C13—C14—C15—C10	54.2 (4)	C28—C29—C30—C25	57.3 (3)

Cg is the centroid of the C16/C17/C22/O3/C23 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24A···O4ii	0.98	2.50	3.425 (4)	156
C29—H29A···Cgii	0.99	2.63	3.552 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C16/C17/C22/O3/C23 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24A⋯O4i	0.98	2.50	3.425 (4)	156
C29—H29A⋯Cgi	0.99	2.63	3.552 (4)	155

Symmetry code: (i) .