2-(4-Fluoro-phen-yl)-5-iodo-3-isopropyl-sulfonyl-1-benzofuran.

There are two symmetry-independent mol-ecules, A and B, in the asymmetric unit of the title compound, C(17)H(14)FIO(3)S. The dihedral angle formed by the 4-fluoro-phenyl ring and the mean plane [r.m.s. deviation = 0.013 (2) Å in mol-ecule A and 0.016 (2) Å in mol-ecule B] of the benzofuran fragment is 57.71 (7)° in mol-ecule A and 44.95 (7)° in mol-ecule B. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds and I⋯O contacts [I⋯O = 3.3646 (15) and 3.2354 (14) Å], forming a three--dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H14FIO3S

M = 444.24

Triclinic,

a = 11.7419 (2) Å

b = 12.8226 (2) Å

c = 12.8474 (2) Å

α = 66.576 (1)°

β = 82.703 (1)°

γ = 67.769 (1)°

V = 1642.36 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.10 mm−1

T = 173 K

0.31 × 0.22 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.594, T max = 0.746

30779 measured reflections

8149 independent reflections

7224 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.060

S = 1.01

8149 reflections

419 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.88 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043218/ld2079sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043218/ld2079Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043218/ld2079Isup3.cml

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

C17H14FIO3S	Z = 4
Mr = 444.24	F(000) = 872
Triclinic, P1	Dx = 1.797 Mg m−3
Hall symbol: -P 1	Melting point: 422.5 K
a = 11.7419 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.8226 (2) Å	Cell parameters from 9874 reflections
c = 12.8474 (2) Å	θ = 2.5–28.3°
α = 66.576 (1)°	µ = 2.10 mm−1
β = 82.703 (1)°	T = 173 K
γ = 67.769 (1)°	Block, colourless
V = 1642.36 (5) Å3	0.31 × 0.22 × 0.22 mm

Bruker SMART APEXII CCD diffractometer	8149 independent reflections
Radiation source: rotating anode	7224 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.7°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −17→16
Tmin = 0.594, Tmax = 0.746	l = −17→17
30779 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)] = 0.025	Hydrogen site location: difference Fourier map
wR(F2) = 0.060	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0258P)2 + 0.967P] where P = (Fo2 + 2Fc2)/3
8149 reflections	(Δ/σ)max = 0.001
419 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.88 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	0.326089 (13)	0.662386 (14)	0.466164 (12)	0.03553 (5)
I2	0.737096 (13)	0.416299 (14)	−0.189163 (12)	0.03660 (5)
S1	0.88239 (4)	0.60922 (4)	0.32898 (4)	0.02482 (10)
S2	0.54126 (4)	0.09203 (4)	0.24522 (4)	0.02417 (10)
F1	1.12323 (18)	0.8849 (3)	−0.18380 (15)	0.0963 (8)
F2	−0.06003 (14)	0.13892 (15)	0.42793 (13)	0.0525 (4)
O1	0.64958 (12)	0.85328 (12)	0.07633 (11)	0.0260 (3)
O2	0.84377 (14)	0.51275 (13)	0.40782 (13)	0.0352 (3)
O3	0.99193 (13)	0.57644 (13)	0.26654 (13)	0.0328 (3)
O4	0.26036 (12)	0.35894 (13)	0.04663 (12)	0.0274 (3)
O5	0.64518 (14)	0.04309 (14)	0.18388 (13)	0.0350 (3)
O6	0.48419 (14)	0.01133 (14)	0.32324 (13)	0.0342 (3)
C1	0.75915 (17)	0.70959 (17)	0.23334 (16)	0.0230 (4)
C2	0.62962 (17)	0.73192 (16)	0.25781 (16)	0.0221 (4)
C3	0.56186 (18)	0.68568 (17)	0.35032 (17)	0.0249 (4)
H3	0.6008	0.6255	0.4205	0.030*
C4	0.43510 (18)	0.73193 (17)	0.33472 (17)	0.0253 (4)
C5	0.37556 (18)	0.82104 (18)	0.23277 (18)	0.0280 (4)
H5	0.2884	0.8496	0.2260	0.034*
C6	0.44196 (18)	0.86794 (18)	0.14196 (17)	0.0276 (4)
H6	0.4030	0.9292	0.0722	0.033*
C7	0.56748 (17)	0.82128 (17)	0.15782 (16)	0.0236 (4)
C8	0.76507 (18)	0.78429 (18)	0.12401 (16)	0.0243 (4)
C9	0.86352 (19)	0.8079 (2)	0.04658 (16)	0.0293 (4)
C10	0.9528 (2)	0.7157 (3)	0.01943 (19)	0.0390 (5)
H10	0.9541	0.6346	0.0539	0.047*
C11	1.0412 (2)	0.7437 (3)	−0.0595 (2)	0.0563 (8)
H11	1.1036	0.6819	−0.0792	0.068*
C12	1.0364 (3)	0.8610 (4)	−0.1074 (2)	0.0602 (9)
C13	0.9495 (3)	0.9538 (3)	−0.0828 (2)	0.0540 (8)
H13	0.9490	1.0346	−0.1184	0.065*
C14	0.8622 (2)	0.9275 (2)	−0.00479 (18)	0.0396 (5)
H14	0.8009	0.9905	0.0142	0.048*
C15	0.90404 (19)	0.6917 (2)	0.40407 (17)	0.0312 (4)
H15	0.9739	0.6348	0.4598	0.037*
C16	0.7904 (2)	0.7301 (2)	0.47178 (19)	0.0403 (5)
H16A	0.8057	0.7705	0.5163	0.060*
H16B	0.7725	0.6579	0.5229	0.060*
H16C	0.7199	0.7865	0.4196	0.060*
C17	0.9410 (2)	0.7973 (2)	0.3244 (2)	0.0382 (5)
H17A	0.8714	0.8591	0.2732	0.057*
H17B	1.0108	0.7679	0.2798	0.057*
H17C	0.9648	0.8333	0.3687	0.057*
C18	0.43388 (17)	0.21427 (17)	0.14277 (16)	0.0240 (4)
C19	0.46896 (18)	0.29646 (17)	0.04048 (16)	0.0242 (4)
C20	0.57969 (18)	0.30585 (19)	−0.00800 (17)	0.0267 (4)
H20	0.6566	0.2501	0.0289	0.032*
C21	0.57303 (19)	0.3995 (2)	−0.11194 (17)	0.0292 (4)
C22	0.4612 (2)	0.4823 (2)	−0.16880 (19)	0.0336 (5)
H22	0.4609	0.5442	−0.2410	0.040*
C23	0.3503 (2)	0.4745 (2)	−0.12006 (18)	0.0324 (4)
H23	0.2732	0.5295	−0.1570	0.039*
C26	0.21380 (17)	0.22260 (18)	0.22001 (16)	0.0249 (4)
C24	0.35885 (18)	0.38246 (19)	−0.01535 (17)	0.0266 (4)
C25	0.30780 (18)	0.25643 (17)	0.14309 (16)	0.0245 (4)
C27	0.21988 (19)	0.10232 (19)	0.27135 (18)	0.0292 (4)
H27	0.2879	0.0395	0.2582	0.035*
C28	0.1273 (2)	0.0737 (2)	0.34156 (18)	0.0327 (4)
H28	0.1309	−0.0082	0.3767	0.039*
C29	0.0304 (2)	0.1664 (2)	0.35910 (18)	0.0334 (5)
C30	0.0208 (2)	0.2862 (2)	0.31029 (19)	0.0343 (5)
H30	−0.0474	0.3481	0.3246	0.041*
C31	0.11328 (19)	0.31421 (19)	0.23962 (18)	0.0295 (4)
H31	0.1082	0.3965	0.2042	0.035*
C32	0.58508 (18)	0.16381 (18)	0.31956 (17)	0.0265 (4)
H32	0.6135	0.2289	0.2633	0.032*
C33	0.6918 (2)	0.0688 (2)	0.40173 (19)	0.0364 (5)
H33A	0.7214	0.1084	0.4381	0.055*
H33B	0.7588	0.0301	0.3601	0.055*
H33C	0.6638	0.0069	0.4598	0.055*
C34	0.4752 (2)	0.2221 (2)	0.3806 (2)	0.0370 (5)
H34A	0.4504	0.1585	0.4399	0.055*
H34B	0.4065	0.2778	0.3260	0.055*
H34C	0.4978	0.2676	0.4151	0.055*

	U11	U22	U33	U12	U13	U23
I1	0.02965 (8)	0.04227 (9)	0.03667 (8)	−0.01834 (6)	0.01302 (6)	−0.01549 (7)
I2	0.03260 (8)	0.04483 (9)	0.03496 (8)	−0.02140 (7)	0.00914 (6)	−0.01315 (7)
S1	0.0195 (2)	0.0205 (2)	0.0256 (2)	−0.00292 (17)	0.00131 (17)	−0.00429 (18)
S2	0.0218 (2)	0.0233 (2)	0.0259 (2)	−0.00656 (18)	0.00033 (18)	−0.00919 (18)
F1	0.0640 (12)	0.188 (3)	0.0504 (10)	−0.0825 (15)	0.0297 (9)	−0.0322 (13)
F2	0.0415 (8)	0.0622 (10)	0.0547 (9)	−0.0280 (7)	0.0253 (7)	−0.0214 (8)
O1	0.0223 (7)	0.0286 (7)	0.0228 (6)	−0.0104 (6)	−0.0003 (5)	−0.0042 (6)
O2	0.0287 (8)	0.0248 (7)	0.0361 (8)	−0.0061 (6)	0.0028 (6)	0.0004 (6)
O3	0.0226 (7)	0.0297 (8)	0.0369 (8)	−0.0030 (6)	0.0058 (6)	−0.0110 (6)
O4	0.0222 (7)	0.0291 (7)	0.0266 (7)	−0.0082 (6)	0.0005 (5)	−0.0074 (6)
O5	0.0281 (8)	0.0360 (8)	0.0377 (8)	−0.0025 (6)	0.0021 (6)	−0.0198 (7)
O6	0.0323 (8)	0.0290 (8)	0.0377 (8)	−0.0141 (6)	−0.0035 (6)	−0.0051 (6)
C1	0.0204 (9)	0.0228 (9)	0.0236 (9)	−0.0076 (7)	0.0031 (7)	−0.0076 (7)
C2	0.0194 (9)	0.0206 (9)	0.0257 (9)	−0.0057 (7)	0.0009 (7)	−0.0098 (7)
C3	0.0241 (9)	0.0218 (9)	0.0256 (9)	−0.0073 (7)	0.0025 (7)	−0.0074 (7)
C4	0.0235 (9)	0.0237 (9)	0.0311 (10)	−0.0103 (8)	0.0070 (8)	−0.0130 (8)
C5	0.0203 (9)	0.0251 (9)	0.0392 (11)	−0.0077 (8)	0.0014 (8)	−0.0133 (9)
C6	0.0228 (9)	0.0242 (9)	0.0308 (10)	−0.0066 (8)	−0.0038 (8)	−0.0057 (8)
C7	0.0234 (9)	0.0228 (9)	0.0235 (9)	−0.0094 (7)	0.0017 (7)	−0.0072 (7)
C8	0.0225 (9)	0.0260 (9)	0.0246 (9)	−0.0088 (8)	0.0002 (7)	−0.0098 (8)
C9	0.0251 (10)	0.0446 (12)	0.0204 (9)	−0.0172 (9)	0.0004 (7)	−0.0101 (9)
C10	0.0270 (11)	0.0594 (15)	0.0297 (11)	−0.0122 (11)	0.0021 (9)	−0.0196 (11)
C11	0.0269 (12)	0.107 (3)	0.0342 (13)	−0.0167 (14)	0.0046 (10)	−0.0342 (15)
C12	0.0439 (15)	0.118 (3)	0.0278 (12)	−0.0539 (18)	0.0096 (11)	−0.0165 (15)
C13	0.0576 (17)	0.084 (2)	0.0306 (12)	−0.0534 (17)	0.0019 (12)	−0.0057 (13)
C14	0.0442 (13)	0.0530 (14)	0.0263 (10)	−0.0310 (12)	−0.0024 (9)	−0.0061 (10)
C15	0.0256 (10)	0.0328 (11)	0.0277 (10)	−0.0045 (8)	−0.0064 (8)	−0.0077 (9)
C16	0.0403 (13)	0.0501 (14)	0.0318 (11)	−0.0132 (11)	0.0049 (10)	−0.0209 (11)
C17	0.0351 (12)	0.0357 (12)	0.0466 (13)	−0.0147 (10)	0.0017 (10)	−0.0168 (10)
C18	0.0217 (9)	0.0266 (9)	0.0241 (9)	−0.0081 (8)	0.0007 (7)	−0.0107 (8)
C19	0.0257 (10)	0.0256 (9)	0.0222 (9)	−0.0090 (8)	−0.0003 (7)	−0.0097 (8)
C20	0.0239 (10)	0.0301 (10)	0.0268 (9)	−0.0098 (8)	0.0012 (8)	−0.0116 (8)
C21	0.0291 (10)	0.0344 (11)	0.0280 (10)	−0.0155 (9)	0.0049 (8)	−0.0130 (9)
C22	0.0369 (12)	0.0332 (11)	0.0279 (10)	−0.0162 (9)	0.0020 (9)	−0.0060 (9)
C23	0.0299 (11)	0.0317 (11)	0.0303 (10)	−0.0092 (9)	−0.0027 (8)	−0.0072 (9)
C26	0.0209 (9)	0.0305 (10)	0.0252 (9)	−0.0088 (8)	0.0009 (7)	−0.0129 (8)
C24	0.0241 (10)	0.0310 (10)	0.0265 (9)	−0.0125 (8)	0.0030 (8)	−0.0110 (8)
C25	0.0261 (10)	0.0233 (9)	0.0244 (9)	−0.0075 (8)	−0.0011 (7)	−0.0103 (8)
C27	0.0233 (10)	0.0288 (10)	0.0364 (11)	−0.0084 (8)	0.0025 (8)	−0.0147 (9)
C28	0.0308 (11)	0.0320 (11)	0.0343 (11)	−0.0148 (9)	0.0009 (9)	−0.0084 (9)
C29	0.0275 (10)	0.0467 (13)	0.0303 (10)	−0.0199 (10)	0.0089 (8)	−0.0151 (10)
C30	0.0273 (11)	0.0399 (12)	0.0364 (11)	−0.0087 (9)	0.0072 (9)	−0.0201 (10)
C31	0.0268 (10)	0.0286 (10)	0.0339 (10)	−0.0090 (8)	0.0027 (8)	−0.0144 (9)
C32	0.0272 (10)	0.0282 (10)	0.0266 (9)	−0.0119 (8)	0.0005 (8)	−0.0110 (8)
C33	0.0315 (11)	0.0394 (12)	0.0364 (11)	−0.0100 (10)	−0.0066 (9)	−0.0129 (10)
C34	0.0345 (12)	0.0410 (12)	0.0374 (12)	−0.0066 (10)	0.0015 (9)	−0.0236 (10)

I1—C4	2.0982 (19)	C15—C17	1.517 (3)
I1—O2i	3.3646 (15)	C15—C16	1.526 (3)
I2—C21	2.098 (2)	C15—H15	1.0000
I2—O3ii	3.2354 (14)	C16—H16A	0.9800
S1—O2	1.4399 (15)	C16—H16B	0.9800
S1—O3	1.4392 (14)	C16—H16C	0.9800
S1—C1	1.7450 (19)	C17—H17A	0.9800
S1—C15	1.787 (2)	C17—H17B	0.9800
S2—O6	1.4331 (16)	C17—H17C	0.9800
S2—O5	1.4400 (15)	C18—C25	1.371 (3)
S2—C18	1.751 (2)	C18—C19	1.448 (3)
S2—C32	1.791 (2)	C19—C24	1.389 (3)
F1—C12	1.357 (3)	C19—C20	1.395 (3)
F2—C29	1.354 (2)	C20—C21	1.383 (3)
O1—C8	1.367 (2)	C20—H20	0.9500
O1—C7	1.377 (2)	C21—C22	1.399 (3)
O4—C25	1.378 (2)	C22—C23	1.392 (3)
O4—C24	1.379 (2)	C22—H22	0.9500
C1—C8	1.361 (3)	C23—C24	1.377 (3)
C1—C2	1.454 (3)	C23—H23	0.9500
C2—C7	1.390 (3)	C26—C27	1.392 (3)
C2—C3	1.398 (3)	C26—C31	1.395 (3)
C3—C4	1.386 (3)	C26—C25	1.459 (3)
C3—H3	0.9500	C27—C28	1.385 (3)
C4—C5	1.396 (3)	C27—H27	0.9500
C5—C6	1.377 (3)	C28—C29	1.373 (3)
C5—H5	0.9500	C28—H28	0.9500
C6—C7	1.372 (3)	C29—C30	1.373 (3)
C6—H6	0.9500	C30—C31	1.385 (3)
C8—C9	1.467 (3)	C30—H30	0.9500
C9—C10	1.384 (3)	C31—H31	0.9500
C9—C14	1.402 (3)	C32—C34	1.522 (3)
C10—C11	1.400 (3)	C32—C33	1.526 (3)
C10—H10	0.9500	C32—H32	1.0000
C11—C12	1.361 (5)	C33—H33A	0.9800
C11—H11	0.9500	C33—H33B	0.9800
C12—C13	1.362 (5)	C33—H33C	0.9800
C13—C14	1.379 (3)	C34—H34A	0.9800
C13—H13	0.9500	C34—H34B	0.9800
C14—H14	0.9500	C34—H34C	0.9800
C4—I1—O2i	152.77 (6)	H16A—C16—H16C	109.5
C21—I2—O3ii	170.66 (6)	H16B—C16—H16C	109.5
O2—S1—O3	117.87 (9)	C15—C17—H17A	109.5
O2—S1—C1	106.58 (9)	C15—C17—H17B	109.5
O3—S1—C1	109.02 (9)	H17A—C17—H17B	109.5
O2—S1—C15	108.55 (10)	C15—C17—H17C	109.5
O3—S1—C15	107.76 (10)	H17A—C17—H17C	109.5
C1—S1—C15	106.54 (9)	H17B—C17—H17C	109.5
O6—S2—O5	118.36 (10)	C25—C18—C19	107.14 (17)
O6—S2—C18	110.60 (9)	C25—C18—S2	129.91 (15)
O5—S2—C18	106.18 (9)	C19—C18—S2	122.84 (14)
O6—S2—C32	108.55 (9)	C24—C19—C20	119.06 (18)
O5—S2—C32	108.78 (9)	C24—C19—C18	105.28 (17)
C18—S2—C32	103.33 (9)	C20—C19—C18	135.65 (18)
C8—O1—C7	107.10 (14)	C21—C20—C19	117.35 (19)
C25—O4—C24	107.14 (15)	C21—C20—H20	121.3
C8—C1—C2	107.13 (17)	C19—C20—H20	121.3
C8—C1—S1	126.98 (15)	C20—C21—C22	122.63 (19)
C2—C1—S1	125.85 (14)	C20—C21—I2	118.79 (15)
C7—C2—C3	119.05 (17)	C22—C21—I2	118.57 (15)
C7—C2—C1	104.66 (16)	C23—C22—C21	120.3 (2)
C3—C2—C1	136.28 (18)	C23—C22—H22	119.9
C4—C3—C2	116.79 (18)	C21—C22—H22	119.9
C4—C3—H3	121.6	C24—C23—C22	116.2 (2)
C2—C3—H3	121.6	C24—C23—H23	121.9
C3—C4—C5	122.73 (18)	C22—C23—H23	121.9
C3—C4—I1	119.58 (15)	C27—C26—C31	119.35 (18)
C5—C4—I1	117.65 (14)	C27—C26—C25	121.84 (17)
C6—C5—C4	120.62 (18)	C31—C26—C25	118.78 (18)
C6—C5—H5	119.7	C23—C24—O4	125.19 (18)
C4—C5—H5	119.7	C23—C24—C19	124.40 (19)
C7—C6—C5	116.33 (18)	O4—C24—C19	110.35 (17)
C7—C6—H6	121.8	C18—C25—O4	110.08 (17)
C5—C6—H6	121.8	C18—C25—C26	136.33 (18)
C6—C7—O1	125.00 (17)	O4—C25—C26	113.56 (16)
C6—C7—C2	124.48 (18)	C28—C27—C26	120.40 (19)
O1—C7—C2	110.49 (16)	C28—C27—H27	119.8
C1—C8—O1	110.61 (16)	C26—C27—H27	119.8
C1—C8—C9	135.85 (18)	C29—C28—C27	118.4 (2)
O1—C8—C9	113.54 (16)	C29—C28—H28	120.8
C10—C9—C14	120.1 (2)	C27—C28—H28	120.8
C10—C9—C8	121.0 (2)	F2—C29—C30	118.2 (2)
C14—C9—C8	118.8 (2)	F2—C29—C28	118.6 (2)
C9—C10—C11	119.1 (3)	C30—C29—C28	123.15 (19)
C9—C10—H10	120.5	C29—C30—C31	118.14 (19)
C11—C10—H10	120.5	C29—C30—H30	120.9
C12—C11—C10	118.9 (3)	C31—C30—H30	120.9
C12—C11—H11	120.6	C30—C31—C26	120.6 (2)
C10—C11—H11	120.6	C30—C31—H31	119.7
C11—C12—F1	117.2 (3)	C26—C31—H31	119.7
C11—C12—C13	123.5 (2)	C34—C32—C33	111.88 (17)
F1—C12—C13	119.3 (3)	C34—C32—S2	110.03 (15)
C12—C13—C14	118.3 (3)	C33—C32—S2	108.70 (14)
C12—C13—H13	120.8	C34—C32—H32	108.7
C14—C13—H13	120.8	C33—C32—H32	108.7
C13—C14—C9	120.2 (3)	S2—C32—H32	108.7
C13—C14—H14	119.9	C32—C33—H33A	109.5
C9—C14—H14	119.9	C32—C33—H33B	109.5
C17—C15—C16	113.35 (19)	H33A—C33—H33B	109.5
C17—C15—S1	110.96 (15)	C32—C33—H33C	109.5
C16—C15—S1	110.46 (16)	H33A—C33—H33C	109.5
C17—C15—H15	107.3	H33B—C33—H33C	109.5
C16—C15—H15	107.3	C32—C34—H34A	109.5
S1—C15—H15	107.3	C32—C34—H34B	109.5
C15—C16—H16A	109.5	H34A—C34—H34B	109.5
C15—C16—H16B	109.5	C32—C34—H34C	109.5
H16A—C16—H16B	109.5	H34A—C34—H34C	109.5
C15—C16—H16C	109.5	H34B—C34—H34C	109.5
O2—S1—C1—C8	−152.76 (18)	O6—S2—C18—C25	17.2 (2)
O3—S1—C1—C8	−24.6 (2)	O5—S2—C18—C25	146.80 (18)
C15—S1—C1—C8	91.48 (19)	C32—S2—C18—C25	−98.80 (19)
O2—S1—C1—C2	29.66 (19)	O6—S2—C18—C19	−167.17 (15)
O3—S1—C1—C2	157.87 (16)	O5—S2—C18—C19	−37.57 (18)
C15—S1—C1—C2	−86.10 (18)	C32—S2—C18—C19	76.83 (17)
C8—C1—C2—C7	−0.2 (2)	C25—C18—C19—C24	−1.1 (2)
S1—C1—C2—C7	177.74 (14)	S2—C18—C19—C24	−177.63 (14)
C8—C1—C2—C3	178.5 (2)	C25—C18—C19—C20	178.6 (2)
S1—C1—C2—C3	−3.6 (3)	S2—C18—C19—C20	2.1 (3)
C7—C2—C3—C4	1.0 (3)	C24—C19—C20—C21	−1.9 (3)
C1—C2—C3—C4	−177.6 (2)	C18—C19—C20—C21	178.4 (2)
C2—C3—C4—C5	−0.5 (3)	C19—C20—C21—C22	−0.5 (3)
C2—C3—C4—I1	177.18 (13)	C19—C20—C21—I2	−179.34 (14)
O2i—I1—C4—C3	−102.08 (18)	O3ii—I2—C21—C20	−30.8 (5)
O2i—I1—C4—C5	75.7 (2)	O3ii—I2—C21—C22	150.3 (3)
C3—C4—C5—C6	−0.4 (3)	C20—C21—C22—C23	1.5 (3)
I1—C4—C5—C6	−178.08 (15)	I2—C21—C22—C23	−179.71 (16)
C4—C5—C6—C7	0.7 (3)	C21—C22—C23—C24	0.1 (3)
C5—C6—C7—O1	177.68 (18)	C22—C23—C24—O4	−179.66 (19)
C5—C6—C7—C2	−0.1 (3)	C22—C23—C24—C19	−2.7 (3)
C8—O1—C7—C6	−178.10 (19)	C25—O4—C24—C23	177.04 (19)
C8—O1—C7—C2	0.0 (2)	C25—O4—C24—C19	−0.2 (2)
C3—C2—C7—C6	−0.7 (3)	C20—C19—C24—C23	3.7 (3)
C1—C2—C7—C6	178.25 (18)	C18—C19—C24—C23	−176.46 (19)
C3—C2—C7—O1	−178.81 (16)	C20—C19—C24—O4	−178.95 (16)
C1—C2—C7—O1	0.2 (2)	C18—C19—C24—O4	0.8 (2)
C2—C1—C8—O1	0.2 (2)	C19—C18—C25—O4	1.0 (2)
S1—C1—C8—O1	−177.71 (14)	S2—C18—C25—O4	177.20 (14)
C2—C1—C8—C9	−179.6 (2)	C19—C18—C25—C26	−176.7 (2)
S1—C1—C8—C9	2.4 (3)	S2—C18—C25—C26	−0.5 (3)
C7—O1—C8—C1	−0.1 (2)	C24—O4—C25—C18	−0.5 (2)
C7—O1—C8—C9	179.75 (16)	C24—O4—C25—C26	177.77 (15)
C1—C8—C9—C10	59.0 (3)	C27—C26—C25—C18	−46.5 (3)
O1—C8—C9—C10	−120.9 (2)	C31—C26—C25—C18	135.5 (2)
C1—C8—C9—C14	−124.5 (3)	C27—C26—C25—O4	135.87 (19)
O1—C8—C9—C14	55.7 (2)	C31—C26—C25—O4	−42.1 (2)
C14—C9—C10—C11	0.1 (3)	C31—C26—C27—C28	−0.2 (3)
C8—C9—C10—C11	176.64 (19)	C25—C26—C27—C28	−178.22 (19)
C9—C10—C11—C12	−0.2 (3)	C26—C27—C28—C29	−0.1 (3)
C10—C11—C12—F1	−179.8 (2)	C27—C28—C29—F2	−179.78 (19)
C10—C11—C12—C13	0.0 (4)	C27—C28—C29—C30	0.1 (3)
C11—C12—C13—C14	0.3 (4)	F2—C29—C30—C31	−179.8 (2)
F1—C12—C13—C14	−179.9 (2)	C28—C29—C30—C31	0.3 (3)
C12—C13—C14—C9	−0.4 (4)	C29—C30—C31—C26	−0.7 (3)
C10—C9—C14—C13	0.2 (3)	C27—C26—C31—C30	0.7 (3)
C8—C9—C14—C13	−176.4 (2)	C25—C26—C31—C30	178.72 (19)
O2—S1—C15—C17	−178.23 (14)	O6—S2—C32—C34	−52.80 (17)
O3—S1—C15—C17	53.08 (17)	O5—S2—C32—C34	177.16 (15)
C1—S1—C15—C17	−63.79 (17)	C18—S2—C32—C34	64.64 (16)
O2—S1—C15—C16	−51.66 (17)	O6—S2—C32—C33	70.04 (16)
O3—S1—C15—C16	179.65 (15)	O5—S2—C32—C33	−60.00 (17)
C1—S1—C15—C16	62.77 (17)	C18—S2—C32—C33	−172.52 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1iii	0.95	2.56	3.418 (2)	150
C15—H15···O2iv	1.00	2.52	3.520 (3)	177
C30—H30···O2v	0.95	2.58	3.463 (3)	155
C31—H31···O3v	0.95	2.58	3.260 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.56	3.418 (2)	150
C15—H15⋯O2ii	1.00	2.52	3.520 (3)	177
C30—H30⋯O2iii	0.95	2.58	3.463 (3)	155
C31—H31⋯O3iii	0.95	2.58	3.260 (2)	129

Symmetry codes: (i) ; (ii) ; (iii) .