2-(4-Meth-oxy-benzyl-idene)-2H-1,3-benzodithiole 1,1,3,3-tetra-oxide.

The title compound, C(15)H(12)O(5)S(2), crystallizes with two mol-ecules in the asymmetric unit. In both mol-ecules, the 1,3-benzodithiole plane and the aryl ring of the anisyl group are not quite coplanar; the corresponding dihedral angles are 20.4 (1) and 18.0 (1)°. π-Stacking [with centroid-centroid distances between 3.5440 (14) and 3.8421 (14) Å] takes place along [100] between the alternating benzodithiole benzene rings of symmetrically independent mol-ecules, and also between the anisyl groups of symmetrically related mol-ecules. Furthermore, mol-ecules are linked through C-H⋯O inter-actions.

Related literature

For background on bis­ulfonyl ethyl­enes, see: Simpkins (1993 ▶); Najera & Yus (1999 ▶); Prilezhaeva (2000 ▶); Nielsen et al. (2010 ▶); Zhu & Lu (2009 ▶); Alba et al. (2010 ▶). For related structures, see: Giacometti et al. (1994 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

C15H12O5S2

M = 336.39

Triclinic,

a = 7.3649 (2) Å

b = 11.4723 (3) Å

c = 17.6114 (5) Å

α = 84.345 (2)°

β = 84.631 (2)°

γ = 71.711 (2)°

V = 1402.89 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 173 K

0.17 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

9496 measured reflections

5124 independent reflections

4435 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.093

S = 1.10

5124 reflections

399 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.38 e Å−3

Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and OLEX2 (Dolomanov et al., 2004 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002826/ld2042sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002826/ld2042Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002826/ld2042Isup3.cml

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

C15H12O5S2	Z = 4
Mr = 336.39	F(000) = 696
Triclinic, P1	Dx = 1.593 (1) Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3649 (2) Å	Cell parameters from 5056 reflections
b = 11.4723 (3) Å	θ = 3.1–25.4°
c = 17.6114 (5) Å	µ = 0.40 mm−1
α = 84.345 (2)°	T = 173 K
β = 84.631 (2)°	Block, yellow
γ = 71.711 (2)°	0.17 × 0.12 × 0.08 mm
V = 1402.89 (7) Å3

Nonius KappaCCD diffractometer	4435 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.019
MONTEL, graded multilayered X-ray optics monochromator	θmax = 25.4°, θmin = 3.3°
CCD; rotation images; thick slices scans	h = −8→8
9496 measured reflections	k = −13→13
5124 independent reflections	l = −20→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.025P)2 + 1.7791P] where P = (Fo2 + 2Fc2)/3
5124 reflections	(Δ/σ)max = 0.001
399 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 2σ(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
S1	0.64347 (9)	0.35339 (5)	0.08928 (3)	0.02238 (14)
S2	0.64751 (9)	0.25433 (6)	0.24987 (3)	0.02422 (15)
O1	0.8215 (3)	0.35541 (16)	0.04909 (10)	0.0295 (4)
O2	0.4828 (3)	0.36877 (16)	0.04470 (9)	0.0289 (4)
O3	0.8294 (3)	0.21116 (17)	0.28301 (10)	0.0323 (4)
O4	0.4931 (3)	0.21619 (17)	0.28849 (10)	0.0336 (4)
O5	0.7530 (3)	−0.12438 (15)	−0.13537 (10)	0.0314 (4)
C1	0.5826 (3)	0.4621 (2)	0.15891 (13)	0.0232 (5)
C2	0.5810 (3)	0.4154 (2)	0.23440 (13)	0.0233 (5)
C3	0.5398 (4)	0.4931 (2)	0.29365 (14)	0.0280 (5)
H3	0.5384	0.4613	0.3455	0.034*
C4	0.5008 (4)	0.6182 (2)	0.27511 (15)	0.0301 (6)
H4	0.4718	0.6731	0.3147	0.036*
C5	0.5035 (4)	0.6643 (2)	0.19921 (15)	0.0297 (6)
H5	0.4773	0.7504	0.1877	0.036*
C6	0.5439 (4)	0.5870 (2)	0.14008 (14)	0.0268 (5)
H6	0.5450	0.6188	0.0882	0.032*
C7	0.6748 (3)	0.2207 (2)	0.15259 (13)	0.0222 (5)
C8	0.7040 (3)	0.1042 (2)	0.13583 (14)	0.0248 (5)
H8	0.7087	0.0476	0.1793	0.030*
C9	0.7299 (3)	0.0493 (2)	0.06317 (14)	0.0237 (5)
C10	0.7700 (3)	0.1060 (2)	−0.00806 (14)	0.0241 (5)
H10	0.7893	0.1844	−0.0101	0.029*
C11	0.7821 (3)	0.0502 (2)	−0.07497 (14)	0.0237 (5)
H11	0.8092	0.0900	−0.1226	0.028*
C12	0.7542 (3)	−0.0654 (2)	−0.07256 (14)	0.0250 (5)
C13	0.7247 (3)	−0.1262 (2)	−0.00221 (15)	0.0273 (5)
H13	0.7134	−0.2067	0.0000	0.033*
C14	0.7122 (3)	−0.0693 (2)	0.06378 (15)	0.0262 (5)
H14	0.6909	−0.1113	0.1114	0.031*
C15	0.7570 (4)	−0.0591 (2)	−0.20891 (15)	0.0328 (6)
H15A	0.8792	−0.0413	−0.2187	0.049*
H15B	0.6512	0.0182	−0.2099	0.049*
H15C	0.7434	−0.1097	−0.2484	0.049*
S3	0.06712 (9)	0.22772 (5)	0.71282 (3)	0.02390 (15)
S4	0.00344 (9)	0.46523 (5)	0.62306 (3)	0.02375 (15)
O6	0.2566 (3)	0.15179 (16)	0.73049 (10)	0.0338 (4)
O7	−0.0825 (3)	0.17105 (16)	0.72510 (10)	0.0349 (4)
O8	0.1567 (3)	0.51075 (16)	0.59109 (10)	0.0331 (4)
O9	−0.1808 (3)	0.52166 (16)	0.59230 (10)	0.0336 (4)
O10	0.3914 (3)	−0.20996 (16)	0.44004 (10)	0.0325 (4)
C16	0.0027 (3)	0.3599 (2)	0.76490 (13)	0.0218 (5)
C17	−0.0216 (3)	0.4715 (2)	0.72270 (13)	0.0218 (5)
C18	−0.0697 (3)	0.5813 (2)	0.75786 (14)	0.0253 (5)
H18	−0.0866	0.6576	0.7285	0.030*
C19	−0.0923 (4)	0.5763 (2)	0.83682 (14)	0.0277 (5)
H19	−0.1233	0.6499	0.8623	0.033*
C20	−0.0701 (4)	0.4644 (2)	0.87937 (14)	0.0284 (5)
H20	−0.0880	0.4630	0.9335	0.034*
C21	−0.0226 (4)	0.3551 (2)	0.84416 (14)	0.0264 (5)
H21	−0.0077	0.2790	0.8734	0.032*
C22	0.0720 (3)	0.3032 (2)	0.62085 (13)	0.0226 (5)
C23	0.1276 (3)	0.2572 (2)	0.55205 (14)	0.0252 (5)
H23	0.1287	0.3184	0.5117	0.030*
C24	0.1858 (3)	0.1340 (2)	0.52707 (13)	0.0234 (5)
C25	0.2688 (4)	0.1172 (2)	0.45215 (13)	0.0261 (5)
H25	0.2797	0.1866	0.4200	0.031*
C26	0.3345 (4)	0.0027 (2)	0.42451 (14)	0.0267 (5)
H26	0.3914	−0.0070	0.3739	0.032*
C27	0.3171 (4)	−0.0996 (2)	0.47123 (14)	0.0247 (5)
C28	0.2291 (3)	−0.0849 (2)	0.54467 (13)	0.0247 (5)
H28	0.2131	−0.1540	0.5757	0.030*
C29	0.1654 (4)	0.0303 (2)	0.57202 (14)	0.0249 (5)
H29	0.1065	0.0398	0.6223	0.030*
C30	0.3957 (5)	−0.3186 (2)	0.48879 (16)	0.0379 (7)
H30A	0.4664	−0.3210	0.5337	0.057*
H30B	0.4592	−0.3917	0.4606	0.057*
H30C	0.2643	−0.3174	0.5054	0.057*

	U11	U22	U33	U12	U13	U23
S1	0.0289 (3)	0.0221 (3)	0.0162 (3)	−0.0091 (2)	−0.0007 (2)	0.0013 (2)
S2	0.0285 (3)	0.0270 (3)	0.0170 (3)	−0.0099 (3)	−0.0010 (2)	0.0032 (2)
O1	0.0348 (10)	0.0310 (10)	0.0238 (9)	−0.0143 (8)	0.0070 (8)	−0.0020 (7)
O2	0.0352 (10)	0.0293 (9)	0.0216 (9)	−0.0074 (8)	−0.0091 (7)	−0.0008 (7)
O3	0.0334 (10)	0.0374 (10)	0.0236 (9)	−0.0074 (8)	−0.0087 (8)	0.0049 (8)
O4	0.0381 (11)	0.0392 (11)	0.0262 (9)	−0.0197 (9)	0.0068 (8)	0.0018 (8)
O5	0.0418 (11)	0.0221 (9)	0.0313 (10)	−0.0111 (8)	0.0000 (8)	−0.0051 (7)
C1	0.0221 (12)	0.0296 (13)	0.0186 (12)	−0.0093 (10)	−0.0020 (9)	−0.0005 (10)
C2	0.0221 (12)	0.0279 (13)	0.0210 (12)	−0.0098 (10)	−0.0017 (9)	0.0011 (10)
C3	0.0313 (14)	0.0360 (14)	0.0180 (12)	−0.0124 (11)	−0.0007 (10)	−0.0024 (10)
C4	0.0285 (14)	0.0353 (15)	0.0255 (13)	−0.0071 (11)	0.0003 (11)	−0.0086 (11)
C5	0.0319 (14)	0.0246 (13)	0.0321 (14)	−0.0075 (11)	−0.0047 (11)	−0.0008 (11)
C6	0.0311 (14)	0.0281 (13)	0.0211 (12)	−0.0092 (11)	−0.0035 (10)	0.0012 (10)
C7	0.0236 (12)	0.0254 (12)	0.0176 (11)	−0.0088 (10)	−0.0011 (9)	0.0024 (9)
C8	0.0226 (12)	0.0263 (13)	0.0241 (12)	−0.0076 (10)	−0.0014 (10)	0.0043 (10)
C9	0.0202 (12)	0.0228 (12)	0.0270 (13)	−0.0056 (10)	−0.0022 (10)	0.0010 (10)
C10	0.0211 (12)	0.0202 (12)	0.0308 (13)	−0.0066 (10)	−0.0005 (10)	−0.0011 (10)
C11	0.0217 (12)	0.0224 (12)	0.0265 (13)	−0.0076 (10)	0.0014 (10)	0.0001 (10)
C12	0.0217 (12)	0.0201 (12)	0.0320 (14)	−0.0045 (10)	−0.0011 (10)	−0.0035 (10)
C13	0.0246 (13)	0.0181 (12)	0.0379 (15)	−0.0056 (10)	−0.0017 (11)	0.0008 (10)
C14	0.0220 (12)	0.0216 (12)	0.0319 (14)	−0.0043 (10)	−0.0019 (10)	0.0043 (10)
C15	0.0423 (16)	0.0279 (14)	0.0289 (14)	−0.0114 (12)	−0.0007 (12)	−0.0054 (11)
S3	0.0316 (3)	0.0185 (3)	0.0196 (3)	−0.0067 (2)	0.0012 (2)	0.0023 (2)
S4	0.0327 (3)	0.0194 (3)	0.0186 (3)	−0.0085 (2)	−0.0012 (2)	0.0021 (2)
O6	0.0394 (11)	0.0259 (9)	0.0274 (10)	0.0017 (8)	−0.0043 (8)	0.0032 (7)
O7	0.0465 (12)	0.0287 (10)	0.0340 (10)	−0.0215 (9)	0.0108 (9)	−0.0037 (8)
O8	0.0471 (12)	0.0310 (10)	0.0262 (9)	−0.0223 (9)	0.0083 (8)	−0.0012 (8)
O9	0.0401 (11)	0.0290 (10)	0.0271 (10)	−0.0034 (8)	−0.0110 (8)	0.0034 (8)
O10	0.0474 (11)	0.0234 (9)	0.0250 (9)	−0.0096 (8)	0.0036 (8)	−0.0035 (7)
C16	0.0196 (12)	0.0212 (12)	0.0238 (12)	−0.0061 (9)	0.0014 (9)	−0.0007 (9)
C17	0.0217 (12)	0.0227 (12)	0.0204 (12)	−0.0072 (10)	−0.0002 (9)	0.0007 (9)
C18	0.0279 (13)	0.0213 (12)	0.0276 (13)	−0.0094 (10)	−0.0006 (10)	−0.0004 (10)
C19	0.0279 (13)	0.0283 (13)	0.0281 (13)	−0.0099 (11)	0.0020 (10)	−0.0070 (10)
C20	0.0287 (13)	0.0337 (14)	0.0221 (13)	−0.0098 (11)	0.0026 (10)	−0.0027 (10)
C21	0.0285 (13)	0.0261 (13)	0.0225 (12)	−0.0072 (10)	−0.0003 (10)	0.0035 (10)
C22	0.0271 (13)	0.0187 (12)	0.0209 (12)	−0.0069 (10)	−0.0002 (10)	0.0020 (9)
C23	0.0276 (13)	0.0264 (13)	0.0211 (12)	−0.0094 (10)	−0.0031 (10)	0.0048 (10)
C24	0.0241 (12)	0.0239 (12)	0.0219 (12)	−0.0064 (10)	−0.0025 (10)	−0.0023 (10)
C25	0.0334 (14)	0.0279 (13)	0.0181 (12)	−0.0126 (11)	−0.0024 (10)	0.0039 (10)
C26	0.0335 (14)	0.0313 (13)	0.0159 (11)	−0.0118 (11)	0.0000 (10)	−0.0005 (10)
C27	0.0284 (13)	0.0248 (13)	0.0214 (12)	−0.0083 (10)	−0.0036 (10)	−0.0029 (10)
C28	0.0287 (13)	0.0257 (13)	0.0201 (12)	−0.0100 (10)	−0.0007 (10)	0.0013 (10)
C29	0.0276 (13)	0.0282 (13)	0.0184 (12)	−0.0091 (10)	0.0009 (10)	−0.0001 (10)
C30	0.0569 (19)	0.0241 (14)	0.0305 (14)	−0.0117 (13)	0.0034 (13)	−0.0003 (11)

S1—O1	1.4360 (18)	S3—O7	1.4353 (18)
S1—O2	1.4362 (18)	S3—O6	1.4380 (19)
S1—C1	1.763 (2)	S3—C22	1.763 (2)
S1—C7	1.763 (2)	S3—C16	1.763 (2)
S2—O3	1.4328 (18)	S4—O8	1.4343 (18)
S2—O4	1.4342 (18)	S4—O9	1.4389 (19)
S2—C2	1.757 (2)	S4—C17	1.754 (2)
S2—C7	1.772 (2)	S4—C22	1.770 (2)
O5—C12	1.354 (3)	O10—C27	1.360 (3)
O5—C15	1.433 (3)	O10—C30	1.436 (3)
C1—C6	1.383 (3)	C16—C17	1.385 (3)
C1—C2	1.384 (3)	C16—C21	1.389 (3)
C2—C3	1.390 (3)	C17—C18	1.388 (3)
C3—C4	1.384 (4)	C18—C19	1.383 (4)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.389 (4)	C19—C20	1.392 (4)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.385 (4)	C20—C21	1.384 (4)
C5—H5	0.9500	C20—H20	0.9500
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.343 (3)	C22—C23	1.346 (3)
C8—C9	1.452 (3)	C23—C24	1.442 (3)
C8—H8	0.9500	C23—H23	0.9500
C9—C14	1.405 (3)	C24—C29	1.404 (3)
C9—C10	1.405 (3)	C24—C25	1.406 (3)
C10—C11	1.378 (3)	C25—C26	1.371 (4)
C10—H10	0.9500	C25—H25	0.9500
C11—C12	1.400 (3)	C26—C27	1.398 (3)
C11—H11	0.9500	C26—H26	0.9500
C12—C13	1.394 (4)	C27—C28	1.393 (3)
C13—C14	1.370 (4)	C28—C29	1.376 (3)
C13—H13	0.9500	C28—H28	0.9500
C14—H14	0.9500	C29—H29	0.9500
C15—H15A	0.9800	C30—H30A	0.9800
C15—H15B	0.9800	C30—H30B	0.9800
C15—H15C	0.9800	C30—H30C	0.9800
O1—S1—O2	117.71 (11)	O7—S3—O6	116.77 (12)
O1—S1—C1	108.95 (11)	O7—S3—C22	112.52 (11)
O2—S1—C1	110.29 (11)	O6—S3—C22	110.41 (11)
O1—S1—C7	111.23 (11)	O7—S3—C16	108.99 (11)
O2—S1—C7	109.43 (11)	O6—S3—C16	109.12 (11)
C1—S1—C7	97.34 (11)	C22—S3—C16	97.21 (11)
O3—S2—O4	117.61 (11)	O8—S4—O9	116.81 (11)
O3—S2—C2	108.98 (11)	O8—S4—C17	110.52 (11)
O4—S2—C2	110.83 (11)	O9—S4—C17	109.14 (11)
O3—S2—C7	110.16 (11)	O8—S4—C22	110.39 (11)
O4—S2—C7	110.04 (11)	O9—S4—C22	110.62 (11)
C2—S2—C7	97.32 (11)	C17—S4—C22	97.69 (11)
C12—O5—C15	118.30 (19)	C27—O10—C30	117.44 (19)
C6—C1—C2	121.2 (2)	C17—C16—C21	120.5 (2)
C6—C1—S1	122.46 (18)	C17—C16—S3	116.57 (18)
C2—C1—S1	116.29 (19)	C21—C16—S3	122.91 (18)
C1—C2—C3	120.8 (2)	C16—C17—C18	121.4 (2)
C1—C2—S2	116.23 (18)	C16—C17—S4	115.80 (18)
C3—C2—S2	122.88 (19)	C18—C17—S4	122.71 (18)
C4—C3—C2	118.2 (2)	C19—C18—C17	118.0 (2)
C4—C3—H3	120.9	C19—C18—H18	121.0
C2—C3—H3	120.9	C17—C18—H18	121.0
C3—C4—C5	120.7 (2)	C18—C19—C20	120.7 (2)
C3—C4—H4	119.7	C18—C19—H19	119.6
C5—C4—H4	119.7	C20—C19—H19	119.6
C6—C5—C4	121.2 (2)	C21—C20—C19	121.2 (2)
C6—C5—H5	119.4	C21—C20—H20	119.4
C4—C5—H5	119.4	C19—C20—H20	119.4
C1—C6—C5	117.9 (2)	C20—C21—C16	118.2 (2)
C1—C6—H6	121.0	C20—C21—H21	120.9
C5—C6—H6	121.0	C16—C21—H21	120.9
C8—C7—S1	128.34 (19)	C23—C22—S3	130.49 (19)
C8—C7—S2	118.91 (18)	C23—C22—S4	116.88 (18)
S1—C7—S2	112.62 (13)	S3—C22—S4	112.52 (13)
C7—C8—C9	131.6 (2)	C22—C23—C24	133.1 (2)
C7—C8—H8	114.2	C22—C23—H23	113.4
C9—C8—H8	114.2	C24—C23—H23	113.4
C14—C9—C10	117.3 (2)	C29—C24—C25	117.9 (2)
C14—C9—C8	117.7 (2)	C29—C24—C23	124.8 (2)
C10—C9—C8	125.0 (2)	C25—C24—C23	117.3 (2)
C11—C10—C9	121.3 (2)	C26—C25—C24	121.3 (2)
C11—C10—H10	119.3	C26—C25—H25	119.3
C9—C10—H10	119.3	C24—C25—H25	119.3
C10—C11—C12	119.8 (2)	C25—C26—C27	119.6 (2)
C10—C11—H11	120.1	C25—C26—H26	120.2
C12—C11—H11	120.1	C27—C26—H26	120.2
O5—C12—C13	116.2 (2)	O10—C27—C28	124.1 (2)
O5—C12—C11	124.1 (2)	O10—C27—C26	115.6 (2)
C13—C12—C11	119.7 (2)	C28—C27—C26	120.2 (2)
C14—C13—C12	119.7 (2)	C29—C28—C27	119.6 (2)
C14—C13—H13	120.1	C29—C28—H28	120.2
C12—C13—H13	120.1	C27—C28—H28	120.2
C13—C14—C9	122.0 (2)	C28—C29—C24	121.3 (2)
C13—C14—H14	119.0	C28—C29—H29	119.3
C9—C14—H14	119.0	C24—C29—H29	119.3
O5—C15—H15A	109.5	O10—C30—H30A	109.5
O5—C15—H15B	109.5	O10—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
O5—C15—H15C	109.5	O10—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5
O1—S1—C1—C6	63.6 (2)	O7—S3—C16—C17	−117.07 (19)
O2—S1—C1—C6	−67.1 (2)	O6—S3—C16—C17	114.37 (19)
C7—S1—C1—C6	179.0 (2)	C22—S3—C16—C17	−0.2 (2)
O1—S1—C1—C2	−114.48 (19)	O7—S3—C16—C21	63.2 (2)
O2—S1—C1—C2	114.90 (19)	O6—S3—C16—C21	−65.4 (2)
C7—S1—C1—C2	1.0 (2)	C22—S3—C16—C21	−180.0 (2)
C6—C1—C2—C3	0.2 (4)	C21—C16—C17—C18	0.7 (4)
S1—C1—C2—C3	178.31 (18)	S3—C16—C17—C18	−179.10 (18)
C6—C1—C2—S2	−176.12 (19)	C21—C16—C17—S4	−177.07 (19)
S1—C1—C2—S2	2.0 (3)	S3—C16—C17—S4	3.2 (3)
O3—S2—C2—C1	110.47 (19)	O8—S4—C17—C16	−119.63 (19)
O4—S2—C2—C1	−118.59 (19)	O9—S4—C17—C16	110.60 (19)
C7—S2—C2—C1	−3.8 (2)	C22—S4—C17—C16	−4.4 (2)
O3—S2—C2—C3	−65.8 (2)	O8—S4—C17—C18	62.7 (2)
O4—S2—C2—C3	65.1 (2)	O9—S4—C17—C18	−67.1 (2)
C7—S2—C2—C3	179.9 (2)	C22—S4—C17—C18	177.9 (2)
C1—C2—C3—C4	−0.2 (4)	C16—C17—C18—C19	0.2 (4)
S2—C2—C3—C4	175.95 (19)	S4—C17—C18—C19	177.78 (19)
C2—C3—C4—C5	−0.2 (4)	C17—C18—C19—C20	−1.0 (4)
C3—C4—C5—C6	0.5 (4)	C18—C19—C20—C21	0.8 (4)
C2—C1—C6—C5	0.0 (4)	C19—C20—C21—C16	0.0 (4)
S1—C1—C6—C5	−177.93 (19)	C17—C16—C21—C20	−0.8 (4)
C4—C5—C6—C1	−0.4 (4)	S3—C16—C21—C20	178.96 (19)
O1—S1—C7—C8	−74.0 (2)	O7—S3—C22—C23	−72.5 (3)
O2—S1—C7—C8	57.7 (3)	O6—S3—C22—C23	60.0 (3)
C1—S1—C7—C8	172.3 (2)	C16—S3—C22—C23	173.5 (2)
O1—S1—C7—S2	110.16 (14)	O7—S3—C22—S4	111.31 (14)
O2—S1—C7—S2	−118.08 (13)	O6—S3—C22—S4	−116.27 (14)
C1—S1—C7—S2	−3.49 (15)	C16—S3—C22—S4	−2.74 (15)
O3—S2—C7—C8	74.7 (2)	O8—S4—C22—C23	−57.4 (2)
O4—S2—C7—C8	−56.5 (2)	O9—S4—C22—C23	73.5 (2)
C2—S2—C7—C8	−171.9 (2)	C17—S4—C22—C23	−172.7 (2)
O3—S2—C7—S1	−109.02 (14)	O8—S4—C22—S3	119.43 (14)
O4—S2—C7—S1	119.71 (13)	O9—S4—C22—S3	−109.73 (14)
C2—S2—C7—S1	4.33 (15)	C17—S4—C22—S3	4.12 (15)
S1—C7—C8—C9	4.0 (4)	S3—C22—C23—C24	6.4 (4)
S2—C7—C8—C9	179.6 (2)	S4—C22—C23—C24	−177.5 (2)
C7—C8—C9—C14	−165.1 (3)	C22—C23—C24—C29	11.6 (4)
C7—C8—C9—C10	14.5 (4)	C22—C23—C24—C25	−168.5 (3)
C14—C9—C10—C11	3.2 (3)	C29—C24—C25—C26	−2.3 (4)
C8—C9—C10—C11	−176.4 (2)	C23—C24—C25—C26	177.7 (2)
C9—C10—C11—C12	−0.1 (4)	C24—C25—C26—C27	0.6 (4)
C15—O5—C12—C13	171.8 (2)	C30—O10—C27—C28	−6.4 (4)
C15—O5—C12—C11	−7.9 (3)	C30—O10—C27—C26	173.3 (2)
C10—C11—C12—O5	176.3 (2)	C25—C26—C27—O10	−178.0 (2)
C10—C11—C12—C13	−3.4 (4)	C25—C26—C27—C28	1.7 (4)
O5—C12—C13—C14	−176.0 (2)	O10—C27—C28—C29	177.4 (2)
C11—C12—C13—C14	3.7 (4)	C26—C27—C28—C29	−2.3 (4)
C12—C13—C14—C9	−0.6 (4)	C27—C28—C29—C24	0.6 (4)
C10—C9—C14—C13	−2.9 (4)	C25—C24—C29—C28	1.7 (4)
C8—C9—C14—C13	176.7 (2)	C23—C24—C29—C28	−178.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.36	3.259 (3)	159
C19—H19···O5ii	0.95	2.46	3.332 (3)	152
C20—H20···O1iii	0.95	2.42	3.252 (3)	146
C23—H23···O9iv	0.95	2.55	3.496 (3)	172
C28—H28···O3v	0.95	2.53	3.282 (3)	137