5-Chloro-3-ethyl-sulfinyl-2-(3-fluoro-phen-yl)-1-benzo-furan.

The asymmetric unit of the title compound, C16H12ClFO2S, contains two independent mol-ecules in which the benzo-furan ring systems are essentially planar, with r.m.s. deviations of 0.007 (1) and 0.013 (1) Å. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds into chains extending along the b axis. These chains are further packed into stacks along the c -axis by S⋯O contacts [3.1898 (11) and 3.1361 (11) Å] involving the sulfinyl groups. In both 3-fluoro-phenyl rings, the F atom is disordered over two positions, with site-occupancy factors of 0.921 (2) and 0.079 (2).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶). For details of sulfin­yl–sulfinyl inter­actions, see: Choi et al. (2008 ▶). For a review of carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C16H12ClFO2S

M = 322.77

Triclinic,

a = 9.5538 (5) Å

b = 11.2638 (5) Å

c = 13.4079 (6) Å

α = 98.739 (2)°

β = 93.733 (3)°

γ = 98.627 (2)°

V = 1404.25 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 173 K

0.39 × 0.30 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.625, T max = 0.746

24991 measured reflections

6456 independent reflections

5012 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.06

6456 reflections

390 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.38 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813018151/fj2636sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018151/fj2636Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018151/fj2636Isup3.cml

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

C16H12ClFO2S	Z = 4
Mr = 322.77	F(000) = 664
Triclinic, P1	Dx = 1.527 Mg m−3
Hall symbol: -P 1	Melting point = 390–391 K
a = 9.5538 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2638 (5) Å	Cell parameters from 7946 reflections
c = 13.4079 (6) Å	θ = 2.5–27.5°
α = 98.739 (2)°	µ = 0.43 mm−1
β = 93.733 (3)°	T = 173 K
γ = 98.627 (2)°	Block, colourless
V = 1404.25 (12) Å3	0.39 × 0.30 × 0.13 mm

Bruker SMART APEXII CCD diffractometer	6456 independent reflections
Radiation source: rotating anode	5012 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.039
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.5°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.625, Tmax = 0.746	l = −17→17
24991 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F2) = 0.102	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0489P)2 + 0.2168P] where P = (Fo2 + 2Fc2)/3
6456 reflections	(Δ/σ)max < 0.001
390 parameters	Δρmax = 0.35 e Å−3
16 restraints	Δρmin = −0.38 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	Occ. (<1)
Cl1	−0.13450 (5)	−0.12001 (5)	0.30389 (4)	0.04416 (14)
S1	0.38869 (4)	0.27480 (4)	0.39795 (3)	0.02455 (11)
O1	0.17196 (11)	0.27468 (11)	0.13349 (7)	0.0289 (3)
O2	0.35241 (13)	0.16152 (11)	0.44212 (9)	0.0352 (3)
C1	0.26850 (16)	0.25654 (15)	0.28734 (11)	0.0233 (3)
C2	0.14620 (16)	0.16187 (15)	0.26000 (11)	0.0242 (3)
C3	0.07727 (16)	0.06820 (15)	0.30474 (12)	0.0275 (4)
H3	0.1102	0.0547	0.3698	0.033*
C4	−0.04107 (17)	−0.00427 (16)	0.25041 (12)	0.0306 (4)
C5	−0.09163 (18)	0.01253 (17)	0.15403 (13)	0.0347 (4)
H5	−0.1726	−0.0404	0.1191	0.042*
C6	−0.02470 (18)	0.10514 (17)	0.10986 (12)	0.0329 (4)
H6	−0.0576	0.1185	0.0447	0.039*
C7	0.09267 (17)	0.17788 (16)	0.16478 (11)	0.0271 (4)
C8	0.28051 (16)	0.32102 (15)	0.20894 (11)	0.0253 (4)
C9	0.37654 (16)	0.42621 (16)	0.18878 (11)	0.0248 (3)
C10	0.50720 (17)	0.46966 (17)	0.24506 (11)	0.0310 (4)
H10	0.5374	0.4289	0.2976	0.037*
C11A	0.59270 (18)	0.57172 (17)	0.22454 (12)	0.0331 (4)	0.9214 (19)
H11	0.6811	0.6004	0.2637	0.040*	0.9214 (19)
C11B	0.59270 (18)	0.57172 (17)	0.22454 (12)	0.0331 (4)	0.08
F1B	0.7030 (8)	0.6258 (10)	0.2897 (7)	0.030 (3)*	0.0786 (19)
C12	0.55272 (18)	0.63305 (17)	0.14834 (12)	0.0338 (4)
H12	0.6115	0.7034	0.1345	0.041*
C13A	0.42413 (19)	0.58787 (17)	0.09344 (12)	0.0348 (4)	0.9214 (19)
F1A	0.37983 (13)	0.64640 (12)	0.01946 (9)	0.0534 (4)	0.9214 (19)
C13B	0.42413 (19)	0.58787 (17)	0.09344 (12)	0.0348 (4)	0.08
H13B	0.3951	0.6286	0.0405	0.042*	0.0786 (19)
C14	0.33604 (18)	0.48750 (16)	0.11115 (12)	0.0316 (4)
H14	0.2481	0.4596	0.0711	0.038*
C15	0.31917 (18)	0.39296 (15)	0.47604 (11)	0.0293 (4)
H15A	0.3804	0.4177	0.5405	0.035*
H15B	0.3233	0.4647	0.4412	0.035*
C16	0.16734 (19)	0.3549 (2)	0.49948 (13)	0.0426 (5)
H16A	0.1039	0.3413	0.4370	0.064*
H16B	0.1396	0.4193	0.5483	0.064*
H16C	0.1604	0.2796	0.5283	0.064*
S2	0.40317 (4)	0.78265 (4)	0.38140 (3)	0.02374 (11)
Cl2	−0.11295 (5)	0.38426 (4)	0.27511 (3)	0.03871 (13)
O3	0.17390 (12)	0.80626 (11)	0.12789 (8)	0.0301 (3)
O4	0.37877 (12)	0.66012 (11)	0.41197 (8)	0.0330 (3)
C17	0.27717 (16)	0.77503 (15)	0.27571 (11)	0.0234 (3)
C18	0.15482 (16)	0.68113 (15)	0.24602 (11)	0.0249 (3)
C19	0.09085 (16)	0.58064 (15)	0.28519 (11)	0.0262 (4)
H19	0.1270	0.5616	0.3475	0.031*
C20	−0.02740 (17)	0.51006 (16)	0.22934 (12)	0.0288 (4)
C21	−0.08279 (18)	0.53538 (18)	0.13732 (12)	0.0344 (4)
H21	−0.1638	0.4836	0.1013	0.041*
C22	−0.02113 (18)	0.63453 (18)	0.09858 (12)	0.0356 (4)
H22	−0.0578	0.6535	0.0364	0.043*
C23	0.09697 (17)	0.70541 (16)	0.15460 (11)	0.0281 (4)
C24	0.28570 (16)	0.84678 (16)	0.20190 (11)	0.0254 (4)
C25	0.38173 (16)	0.95328 (15)	0.18337 (11)	0.0244 (3)
C26	0.50607 (17)	1.00255 (17)	0.24596 (11)	0.0305 (4)
H26	0.5304	0.9670	0.3032	0.037*
C27A	0.59358 (18)	1.10291 (17)	0.22457 (12)	0.0321 (4)	0.9214 (19)
H27A	0.6781	1.1352	0.2675	0.039*	0.9214 (19)
C27B	0.59358 (18)	1.10291 (17)	0.22457 (12)	0.0321 (4)	0.08
F2B	0.7032 (9)	1.1542 (11)	0.2920 (7)	0.032 (3)*	0.0786 (19)
C28	0.56134 (18)	1.15759 (16)	0.14231 (12)	0.0322 (4)
H28	0.6217	1.2268	0.1279	0.039*
C29A	0.43791 (19)	1.10749 (17)	0.08194 (11)	0.0315 (4)	0.9214 (19)
F2A	0.40153 (13)	1.15850 (12)	0.00136 (9)	0.0489 (4)	0.9214 (19)
C29B	0.43791 (19)	1.10749 (17)	0.08194 (11)	0.0315 (4)	0.08
H29B	0.4137	1.1440	0.0252	0.038*	0.0786 (19)
C30	0.34884 (17)	1.00771 (16)	0.09992 (11)	0.0289 (4)
H30	0.2653	0.9757	0.0560	0.035*
C31	0.32775 (18)	0.88245 (16)	0.47356 (11)	0.0300 (4)
H31A	0.3924	0.9023	0.5367	0.036*
H31B	0.3216	0.9594	0.4476	0.036*
C32	0.18165 (19)	0.8292 (2)	0.49831 (13)	0.0429 (5)
H32A	0.1139	0.8195	0.4384	0.064*
H32B	0.1515	0.8839	0.5539	0.064*
H32C	0.1849	0.7496	0.5187	0.064*

	U11	U22	U33	U12	U13	U23
Cl1	0.0380 (3)	0.0344 (3)	0.0567 (3)	−0.0087 (2)	−0.0048 (2)	0.0149 (2)
S1	0.0232 (2)	0.0241 (2)	0.02548 (18)	0.00255 (18)	−0.00470 (14)	0.00573 (16)
O1	0.0275 (6)	0.0343 (7)	0.0229 (5)	−0.0012 (5)	−0.0040 (4)	0.0070 (5)
O2	0.0408 (7)	0.0226 (6)	0.0411 (6)	0.0019 (6)	−0.0127 (5)	0.0119 (5)
C1	0.0205 (8)	0.0241 (9)	0.0239 (7)	0.0019 (7)	−0.0016 (6)	0.0025 (6)
C2	0.0215 (8)	0.0243 (9)	0.0255 (7)	0.0042 (7)	0.0005 (6)	0.0007 (7)
C3	0.0264 (8)	0.0269 (9)	0.0290 (7)	0.0054 (8)	−0.0013 (6)	0.0043 (7)
C4	0.0265 (9)	0.0249 (9)	0.0386 (9)	0.0010 (8)	0.0009 (7)	0.0036 (8)
C5	0.0275 (9)	0.0344 (11)	0.0363 (9)	−0.0016 (8)	−0.0065 (7)	−0.0022 (8)
C6	0.0295 (9)	0.0370 (11)	0.0284 (8)	−0.0006 (8)	−0.0056 (7)	0.0028 (8)
C7	0.0247 (8)	0.0291 (9)	0.0256 (7)	0.0010 (8)	−0.0003 (6)	0.0031 (7)
C8	0.0237 (8)	0.0284 (9)	0.0217 (7)	0.0031 (7)	−0.0025 (6)	0.0007 (7)
C9	0.0249 (8)	0.0276 (9)	0.0215 (7)	0.0036 (7)	0.0031 (6)	0.0026 (7)
C10	0.0297 (9)	0.0363 (10)	0.0264 (7)	0.0022 (8)	−0.0006 (6)	0.0078 (7)
C11A	0.0258 (9)	0.0396 (11)	0.0308 (8)	−0.0028 (8)	−0.0004 (7)	0.0051 (8)
C11B	0.0258 (9)	0.0396 (11)	0.0308 (8)	−0.0028 (8)	−0.0004 (7)	0.0051 (8)
C12	0.0333 (9)	0.0322 (10)	0.0345 (8)	−0.0017 (8)	0.0066 (7)	0.0070 (8)
C13A	0.0372 (10)	0.0347 (11)	0.0332 (8)	0.0036 (9)	−0.0002 (7)	0.0110 (8)
F1A	0.0534 (8)	0.0501 (8)	0.0576 (8)	−0.0056 (7)	−0.0120 (6)	0.0330 (7)
C13B	0.0372 (10)	0.0347 (11)	0.0332 (8)	0.0036 (9)	−0.0002 (7)	0.0110 (8)
C14	0.0295 (9)	0.0328 (10)	0.0305 (8)	0.0018 (8)	−0.0049 (7)	0.0057 (8)
C15	0.0364 (9)	0.0222 (9)	0.0272 (7)	0.0036 (8)	−0.0045 (6)	0.0015 (7)
C16	0.0401 (10)	0.0538 (14)	0.0330 (9)	0.0109 (10)	0.0054 (8)	0.0005 (9)
S2	0.0216 (2)	0.0232 (2)	0.02581 (18)	0.00206 (17)	−0.00403 (14)	0.00636 (16)
Cl2	0.0344 (2)	0.0282 (2)	0.0503 (3)	−0.0054 (2)	−0.00282 (19)	0.0093 (2)
O3	0.0279 (6)	0.0360 (7)	0.0233 (5)	−0.0045 (6)	−0.0051 (4)	0.0084 (5)
O4	0.0357 (7)	0.0216 (6)	0.0410 (6)	0.0048 (6)	−0.0089 (5)	0.0084 (5)
C17	0.0208 (8)	0.0243 (9)	0.0233 (7)	0.0010 (7)	−0.0019 (6)	0.0025 (6)
C18	0.0223 (8)	0.0271 (9)	0.0235 (7)	0.0027 (7)	−0.0002 (6)	0.0005 (7)
C19	0.0245 (8)	0.0245 (9)	0.0285 (7)	0.0020 (7)	0.0012 (6)	0.0037 (7)
C20	0.0254 (8)	0.0253 (9)	0.0334 (8)	−0.0005 (8)	0.0026 (6)	0.0018 (7)
C21	0.0279 (9)	0.0379 (11)	0.0314 (8)	−0.0052 (8)	−0.0046 (7)	−0.0002 (8)
C22	0.0317 (9)	0.0431 (12)	0.0276 (8)	−0.0041 (9)	−0.0071 (7)	0.0064 (8)
C23	0.0264 (8)	0.0306 (10)	0.0248 (7)	−0.0022 (8)	−0.0007 (6)	0.0048 (7)
C24	0.0220 (8)	0.0302 (9)	0.0219 (7)	0.0025 (7)	−0.0012 (6)	0.0015 (7)
C25	0.0245 (8)	0.0261 (9)	0.0218 (7)	0.0036 (7)	0.0028 (6)	0.0023 (7)
C26	0.0300 (9)	0.0350 (10)	0.0250 (7)	0.0001 (8)	−0.0014 (6)	0.0069 (7)
C27A	0.0273 (9)	0.0352 (11)	0.0301 (8)	−0.0023 (8)	−0.0027 (7)	0.0030 (8)
C27B	0.0273 (9)	0.0352 (11)	0.0301 (8)	−0.0023 (8)	−0.0027 (7)	0.0030 (8)
C28	0.0331 (9)	0.0281 (10)	0.0347 (8)	−0.0006 (8)	0.0087 (7)	0.0065 (8)
C29A	0.0356 (10)	0.0327 (10)	0.0278 (8)	0.0057 (8)	0.0020 (7)	0.0101 (7)
F2A	0.0538 (8)	0.0487 (8)	0.0449 (6)	−0.0046 (6)	−0.0063 (5)	0.0272 (6)
C29B	0.0356 (10)	0.0327 (10)	0.0278 (8)	0.0057 (8)	0.0020 (7)	0.0101 (7)
C30	0.0285 (9)	0.0313 (10)	0.0261 (7)	0.0028 (8)	−0.0013 (6)	0.0055 (7)
C31	0.0354 (9)	0.0245 (9)	0.0271 (7)	0.0049 (8)	−0.0062 (6)	−0.0011 (7)
C32	0.0381 (10)	0.0522 (13)	0.0365 (9)	0.0083 (10)	0.0069 (8)	−0.0015 (9)

Cl1—C4	1.7403 (18)	S2—O4	1.4882 (12)
S1—O2	1.4909 (12)	S2—C17	1.7818 (14)
S1—C1	1.7818 (14)	S2—C31	1.8018 (16)
S1—C15	1.8003 (16)	S2—O2i	3.1361 (11)
S1—O4i	3.1898 (11)	Cl2—C20	1.7420 (18)
O1—C7	1.368 (2)	O3—C23	1.366 (2)
O1—C8	1.3827 (17)	O3—C24	1.3828 (17)
C1—C8	1.367 (2)	C17—C24	1.368 (2)
C1—C2	1.445 (2)	C17—C18	1.444 (2)
C2—C7	1.392 (2)	C18—C23	1.394 (2)
C2—C3	1.394 (2)	C18—C19	1.395 (2)
C3—C4	1.382 (2)	C19—C20	1.381 (2)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.400 (2)	C20—C21	1.397 (2)
C5—C6	1.373 (3)	C21—C22	1.372 (3)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.380 (2)	C22—C23	1.383 (2)
C6—H6	0.9500	C22—H22	0.9500
C8—C9	1.457 (2)	C24—C25	1.460 (2)
C9—C10	1.396 (2)	C25—C30	1.395 (2)
C9—C14	1.398 (2)	C25—C26	1.398 (2)
C10—C11A	1.381 (2)	C26—C27A	1.380 (2)
C10—H10	0.9500	C26—H26	0.9500
C11A—C12	1.382 (2)	C27A—C28	1.382 (2)
C11A—H11	0.9500	C27A—H27A	0.9500
C12—C13A	1.375 (2)	C28—C29A	1.379 (2)
C12—H12	0.9500	C28—H28	0.9500
C13A—F1A	1.3511 (18)	C29A—F2A	1.3483 (17)
C13A—C14	1.366 (2)	C29A—C30	1.367 (2)
C14—H14	0.9500	C30—H30	0.9500
C15—C16	1.517 (2)	C31—C32	1.513 (2)
C15—H15A	0.9900	C31—H31A	0.9900
C15—H15B	0.9900	C31—H31B	0.9900
C16—H16A	0.9800	C32—H32A	0.9800
C16—H16B	0.9800	C32—H32B	0.9800
C16—H16C	0.9800	C32—H32C	0.9800
O2—S1—C1	105.42 (7)	O4—S2—C17	105.65 (7)
O2—S1—C15	106.75 (8)	O4—S2—C31	106.46 (8)
C1—S1—C15	99.12 (7)	C17—S2—C31	98.92 (7)
O2—S1—O4i	81.93 (5)	O4—S2—O2i	83.93 (5)
C1—S1—O4i	172.64 (6)	C17—S2—O2i	170.27 (6)
C15—S1—O4i	78.70 (5)	C31—S2—O2i	79.57 (6)
C7—O1—C8	106.76 (12)	C23—O3—C24	106.83 (12)
C8—C1—C2	107.21 (13)	C24—C17—C18	107.22 (13)
C8—C1—S1	127.12 (13)	C24—C17—S2	127.16 (13)
C2—C1—S1	125.44 (12)	C18—C17—S2	125.23 (12)
C7—C2—C3	118.94 (14)	C23—C18—C19	119.15 (14)
C7—C2—C1	104.89 (14)	C23—C18—C17	104.89 (14)
C3—C2—C1	136.17 (14)	C19—C18—C17	135.95 (14)
C4—C3—C2	117.18 (14)	C20—C19—C18	117.03 (14)
C4—C3—H3	121.4	C20—C19—H19	121.5
C2—C3—H3	121.4	C18—C19—H19	121.5
C3—C4—C5	122.81 (16)	C19—C20—C21	122.87 (16)
C3—C4—Cl1	119.26 (13)	C19—C20—Cl2	119.11 (13)
C5—C4—Cl1	117.91 (13)	C21—C20—Cl2	118.02 (13)
C6—C5—C4	120.26 (16)	C22—C21—C20	120.49 (15)
C6—C5—H5	119.9	C22—C21—H21	119.8
C4—C5—H5	119.9	C20—C21—H21	119.8
C5—C6—C7	116.70 (15)	C21—C22—C23	116.67 (15)
C5—C6—H6	121.7	C21—C22—H22	121.7
C7—C6—H6	121.7	C23—C22—H22	121.7
O1—C7—C6	124.97 (14)	O3—C23—C22	125.29 (14)
O1—C7—C2	110.93 (13)	O3—C23—C18	110.92 (14)
C6—C7—C2	124.10 (16)	C22—C23—C18	123.78 (16)
C1—C8—O1	110.19 (14)	C17—C24—O3	110.12 (14)
C1—C8—C9	135.22 (14)	C17—C24—C25	135.92 (14)
O1—C8—C9	114.56 (13)	O3—C24—C25	113.97 (13)
C10—C9—C14	118.43 (16)	C30—C25—C26	118.65 (16)
C10—C9—C8	122.51 (14)	C30—C25—C24	118.94 (14)
C14—C9—C8	119.05 (15)	C26—C25—C24	122.41 (14)
C11A—C10—C9	120.21 (15)	C27A—C26—C25	120.02 (15)
C11A—C10—H10	119.9	C27A—C26—H26	120.0
C9—C10—H10	119.9	C25—C26—H26	120.0
C10—C11A—C12	121.57 (16)	C26—C27A—C28	121.64 (16)
C10—C11A—H11	119.2	C26—C27A—H27A	119.2
C12—C11A—H11	119.2	C28—C27A—H27A	119.2
C13A—C12—C11A	117.11 (17)	C29A—C28—C27A	117.21 (17)
C13A—C12—H12	121.4	C29A—C28—H28	121.4
C11A—C12—H12	121.4	C27A—C28—H28	121.4
F1A—C13A—C14	117.61 (15)	F2A—C29A—C30	117.67 (15)
F1A—C13A—C12	119.02 (17)	F2A—C29A—C28	119.27 (16)
C14—C13A—C12	123.35 (16)	C30—C29A—C28	123.06 (15)
C13A—C14—C9	119.32 (16)	C29A—C30—C25	119.42 (15)
C13A—C14—H14	120.3	C29A—C30—H30	120.3
C9—C14—H14	120.3	C25—C30—H30	120.3
C16—C15—S1	113.45 (12)	C32—C31—S2	113.71 (12)
C16—C15—H15A	108.9	C32—C31—H31A	108.8
S1—C15—H15A	108.9	S2—C31—H31A	108.8
C16—C15—H15B	108.9	C32—C31—H31B	108.8
S1—C15—H15B	108.9	S2—C31—H31B	108.8
H15A—C15—H15B	107.7	H31A—C31—H31B	107.7
C15—C16—H16A	109.5	C31—C32—H32A	109.5
C15—C16—H16B	109.5	C31—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C15—C16—H16C	109.5	C31—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5
O2—S1—C1—C8	−163.19 (14)	O4—S2—C17—C24	−156.94 (14)
C15—S1—C1—C8	86.50 (16)	C31—S2—C17—C24	93.07 (15)
O2—S1—C1—C2	10.59 (15)	O4—S2—C17—C18	15.04 (15)
C15—S1—C1—C2	−99.72 (14)	C31—S2—C17—C18	−94.95 (14)
C8—C1—C2—C7	−0.25 (17)	C24—C17—C18—C23	−0.64 (17)
S1—C1—C2—C7	−175.06 (12)	S2—C17—C18—C23	−173.96 (12)
C8—C1—C2—C3	−179.73 (17)	C24—C17—C18—C19	178.21 (17)
S1—C1—C2—C3	5.5 (3)	S2—C17—C18—C19	4.9 (3)
C7—C2—C3—C4	0.4 (2)	C23—C18—C19—C20	0.4 (2)
C1—C2—C3—C4	179.85 (17)	C17—C18—C19—C20	−178.33 (17)
C2—C3—C4—C5	0.6 (2)	C18—C19—C20—C21	0.2 (2)
C2—C3—C4—Cl1	−178.21 (12)	C18—C19—C20—Cl2	−179.33 (12)
C3—C4—C5—C6	−1.0 (3)	C19—C20—C21—C22	−0.7 (3)
Cl1—C4—C5—C6	177.79 (14)	Cl2—C20—C21—C22	178.87 (14)
C4—C5—C6—C7	0.4 (3)	C20—C21—C22—C23	0.5 (3)
C8—O1—C7—C6	−178.81 (16)	C24—O3—C23—C22	−177.52 (16)
C8—O1—C7—C2	1.10 (17)	C24—O3—C23—C18	1.39 (18)
C5—C6—C7—O1	−179.50 (15)	C21—C22—C23—O3	178.95 (16)
C5—C6—C7—C2	0.6 (3)	C21—C22—C23—C18	0.2 (3)
C3—C2—C7—O1	179.06 (13)	C19—C18—C23—O3	−179.56 (13)
C1—C2—C7—O1	−0.53 (17)	C17—C18—C23—O3	−0.47 (18)
C3—C2—C7—C6	−1.0 (2)	C19—C18—C23—C22	−0.6 (3)
C1—C2—C7—C6	179.38 (16)	C17—C18—C23—C22	178.46 (16)
C2—C1—C8—O1	0.93 (18)	C18—C17—C24—O3	1.52 (17)
S1—C1—C8—O1	175.63 (11)	S2—C17—C24—O3	174.67 (11)
C2—C1—C8—C9	178.96 (17)	C18—C17—C24—C25	−178.78 (17)
S1—C1—C8—C9	−6.3 (3)	S2—C17—C24—C25	−5.6 (3)
C7—O1—C8—C1	−1.25 (17)	C23—O3—C24—C17	−1.81 (17)
C7—O1—C8—C9	−179.72 (13)	C23—O3—C24—C25	178.42 (13)
C1—C8—C9—C10	15.5 (3)	C17—C24—C25—C30	−175.60 (17)
O1—C8—C9—C10	−166.56 (14)	O3—C24—C25—C30	4.1 (2)
C1—C8—C9—C14	−163.57 (18)	C17—C24—C25—C26	4.7 (3)
O1—C8—C9—C14	14.4 (2)	O3—C24—C25—C26	−175.58 (14)
C14—C9—C10—C11A	0.7 (2)	C30—C25—C26—C27A	−0.1 (2)
C8—C9—C10—C11A	−178.31 (15)	C24—C25—C26—C27A	179.58 (15)
C9—C10—C11A—C12	−0.3 (3)	C25—C26—C27A—C28	0.4 (3)
C10—C11A—C12—C13A	−0.2 (3)	C26—C27A—C28—C29A	−0.2 (3)
C11A—C12—C13A—F1A	178.81 (16)	C27A—C28—C29A—F2A	179.40 (16)
C11A—C12—C13A—C14	0.3 (3)	C27A—C28—C29A—C30	−0.3 (3)
F1A—C13A—C14—C9	−178.42 (15)	F2A—C29A—C30—C25	−179.12 (14)
C12—C13A—C14—C9	0.1 (3)	C28—C29A—C30—C25	0.6 (3)
C10—C9—C14—C13A	−0.6 (2)	C26—C25—C30—C29A	−0.4 (2)
C8—C9—C14—C13A	178.48 (15)	C24—C25—C30—C29A	179.94 (15)
O2—S1—C15—C16	−46.90 (13)	O4—S2—C31—C32	−45.51 (14)
C1—S1—C15—C16	62.34 (13)	C17—S2—C31—C32	63.82 (14)
O4i—S1—C15—C16	−124.80 (12)	O2i—S2—C31—C32	−125.93 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O4	0.99	2.28	3.233 (2)	160
C31—H31B···O2ii	0.99	2.26	3.211 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O4	0.99	2.28	3.233 (2)	160
C31—H31B⋯O2i	0.99	2.26	3.211 (2)	160

Symmetry code: (i) .