5-Chloro-2-methyl-3-phenyl-sulfonyl-1-benzofuran.

The title compound, C(15)H(11)ClO(3)S, was prepared by the oxidation of 5-chloro-2-methyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. There are two symmetry-independent mol-ecules in the asymmetric unit. The dihedral angles formed by the phenyl ring and the plane of the benzofuran system are 77.80 (8) and 78.34 (8)°. The crystal structure is stabilized by aromatic π-π stacking inter-actions between the furan ring and the benzene rings of neighbouring benzofuran fragments from two symmetry-independent mol-ecules; the centroid-centroid distances within the stacks are 3.689 (4), 3.702 (4), 3.825 (4) and 3.826 (4) Å. Additionally, the stacked mol-ecules exhibit inter- and intra-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 2-methyl-3-phenyl­sulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C15H11ClO3S

M = 306.76

Triclinic,

a = 7.4029 (7) Å

b = 9.2669 (9) Å

c = 20.889 (2) Å

α = 100.953 (2)°

β = 95.626 (2)°

γ = 104.212 (2)°

V = 1348.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 173 (2) K

0.50 × 0.50 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.795, T max = 0.870

9232 measured reflections

4555 independent reflections

4119 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.116

S = 1.16

4555 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536808015699/rk2091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015699/rk2091Isup2.hkl

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

C15H11ClO3S	Z = 4
Mr = 306.76	F000 = 632
Triclinic, P1	Dx = 1.512 Mg m−3
Hall symbol: -P 1	Melting point = 468–469 K
a = 7.4029 (7) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.2669 (9) Å	Cell parameters from 7490 reflections
c = 20.889 (2) Å	θ = 2.3–28.2º
α = 100.953 (2)º	µ = 0.44 mm−1
β = 95.626 (2)º	T = 173 (2) K
γ = 104.212 (2)º	Block, colourless
V = 1348.0 (2) Å3	0.50 × 0.50 × 0.30 mm

Bruker SMART CCD diffractometer	4555 independent reflections
Radiation source: fine-focus sealed tube	4119 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
Detector resolution: 10.0 pixels mm-1	θmax = 25.0º
T = 173(2) K	θmin = 1.0º
φ and ω scans	h = −8→8
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	k = −11→11
Tmin = 0.795, Tmax = 0.870	l = −24→24
9232 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0289P)2 + 1.6847P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max < 0.001
4555 reflections	Δρmax = 0.36 e Å−3
363 parameters	Δρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 >σ(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
Cl1	0.94027 (12)	0.83729 (9)	0.68782 (4)	0.0390 (2)
S1	0.89392 (10)	0.73758 (8)	0.38915 (3)	0.02487 (18)
O1	0.6676 (3)	0.3633 (2)	0.44767 (10)	0.0285 (4)
O2	0.9367 (3)	0.6705 (3)	0.32655 (10)	0.0344 (5)
O3	1.0381 (3)	0.8528 (2)	0.43567 (10)	0.0327 (5)
C1	0.8078 (4)	0.5920 (3)	0.42946 (13)	0.0235 (6)
C2	0.8110 (4)	0.6091 (3)	0.50012 (13)	0.0219 (6)
C3	0.8793 (4)	0.7294 (3)	0.55589 (13)	0.0242 (6)
H3	0.9389	0.8302	0.5524	0.029*
C4	0.8551 (4)	0.6929 (3)	0.61626 (14)	0.0265 (6)
C5	0.7692 (4)	0.5459 (4)	0.62322 (14)	0.0297 (6)
H5	0.7575	0.5271	0.6660	0.036*
C6	0.7012 (4)	0.4275 (3)	0.56827 (15)	0.0303 (7)
H6	0.6421	0.3266	0.5718	0.036*
C7	0.7242 (4)	0.4643 (3)	0.50790 (14)	0.0242 (6)
C8	0.7201 (4)	0.4438 (3)	0.40081 (14)	0.0262 (6)
C9	0.7018 (4)	0.8137 (3)	0.37439 (14)	0.0246 (6)
C10	0.5757 (4)	0.7514 (4)	0.31622 (15)	0.0311 (7)
H10	0.5941	0.6705	0.2843	0.037*
C11	0.4221 (5)	0.8097 (4)	0.30559 (18)	0.0406 (8)
H11	0.3351	0.7694	0.2659	0.049*
C12	0.3958 (5)	0.9256 (4)	0.3524 (2)	0.0445 (9)
H12	0.2897	0.9641	0.3449	0.053*
C13	0.5210 (5)	0.9865 (4)	0.40995 (19)	0.0421 (8)
H13	0.5015	1.0672	0.4417	0.051*
C14	0.6760 (4)	0.9309 (3)	0.42202 (16)	0.0316 (7)
H14	0.7624	0.9719	0.4619	0.038*
C15	0.6662 (5)	0.3533 (4)	0.33182 (15)	0.0352 (7)
H15A	0.7152	0.4174	0.3017	0.053*
H15B	0.5285	0.3172	0.3212	0.053*
H15C	0.7193	0.2655	0.3270	0.053*
Cl2	0.24348 (13)	0.14348 (9)	−0.18646 (4)	0.0400 (2)
S2	0.49179 (10)	0.35480 (8)	0.11049 (3)	0.02486 (18)
O4	0.2303 (3)	−0.0834 (2)	0.05447 (10)	0.0303 (5)
O5	0.5910 (3)	0.4231 (2)	0.06317 (10)	0.0315 (5)
O6	0.5927 (3)	0.3559 (3)	0.17302 (10)	0.0339 (5)
C16	0.3752 (4)	0.1665 (3)	0.07152 (14)	0.0236 (6)
C17	0.3089 (4)	0.1109 (3)	0.00122 (13)	0.0225 (6)
C18	0.3154 (4)	0.1733 (3)	−0.05452 (13)	0.0241 (6)
H18	0.3716	0.2787	−0.0515	0.029*
C19	0.2356 (4)	0.0736 (3)	−0.11451 (14)	0.0274 (6)
C20	0.1522 (4)	−0.0821 (3)	−0.12108 (15)	0.0309 (7)
H20	0.1012	−0.1456	−0.1635	0.037*
C21	0.1440 (4)	−0.1436 (3)	−0.06597 (15)	0.0315 (7)
H21	0.0877	−0.2489	−0.0690	0.038*
C22	0.2222 (4)	−0.0437 (3)	−0.00587 (14)	0.0244 (6)
C23	0.3230 (4)	0.0464 (3)	0.10065 (14)	0.0276 (6)
C24	0.3087 (4)	0.4413 (3)	0.12603 (14)	0.0254 (6)
C25	0.2273 (4)	0.4267 (3)	0.18244 (15)	0.0317 (7)
H25	0.2729	0.3742	0.2126	0.038*
C26	0.0798 (5)	0.4891 (4)	0.19426 (17)	0.0408 (8)
H26	0.0228	0.4797	0.2326	0.049*
C27	0.0152 (5)	0.5653 (4)	0.15001 (19)	0.0447 (9)
H27	−0.0866	0.6083	0.1582	0.054*
C28	0.0965 (5)	0.5797 (4)	0.0943 (2)	0.0442 (9)
H28	0.0508	0.6328	0.0645	0.053*
C29	0.2448 (4)	0.5171 (3)	0.08137 (17)	0.0348 (7)
H29	0.3010	0.5262	0.0428	0.042*
C30	0.3420 (5)	0.0266 (4)	0.16940 (16)	0.0396 (8)
H30A	0.4237	0.1205	0.1984	0.059*
H30B	0.3975	−0.0583	0.1720	0.059*
H30C	0.2173	0.0044	0.1833	0.059*

	U11	U22	U33	U12	U13	U23
Cl1	0.0524 (5)	0.0418 (5)	0.0215 (4)	0.0176 (4)	0.0002 (3)	−0.0001 (3)
S1	0.0231 (4)	0.0292 (4)	0.0215 (4)	0.0035 (3)	0.0058 (3)	0.0071 (3)
O1	0.0314 (11)	0.0232 (10)	0.0290 (11)	0.0051 (9)	0.0025 (9)	0.0052 (8)
O2	0.0362 (12)	0.0446 (13)	0.0254 (11)	0.0126 (10)	0.0133 (9)	0.0088 (9)
O3	0.0260 (11)	0.0348 (12)	0.0316 (12)	−0.0031 (9)	0.0010 (9)	0.0100 (9)
C1	0.0207 (14)	0.0289 (15)	0.0217 (14)	0.0066 (11)	0.0044 (11)	0.0070 (11)
C2	0.0173 (13)	0.0282 (14)	0.0217 (14)	0.0063 (11)	0.0039 (11)	0.0084 (11)
C3	0.0222 (14)	0.0257 (14)	0.0239 (14)	0.0057 (11)	0.0023 (11)	0.0054 (11)
C4	0.0273 (15)	0.0319 (16)	0.0218 (14)	0.0123 (12)	0.0035 (12)	0.0040 (12)
C5	0.0320 (16)	0.0381 (17)	0.0239 (15)	0.0135 (13)	0.0068 (13)	0.0125 (13)
C6	0.0304 (16)	0.0303 (16)	0.0351 (17)	0.0089 (13)	0.0093 (13)	0.0160 (13)
C7	0.0221 (14)	0.0243 (14)	0.0259 (15)	0.0074 (11)	0.0003 (11)	0.0051 (11)
C8	0.0241 (14)	0.0311 (15)	0.0242 (15)	0.0091 (12)	0.0036 (12)	0.0062 (12)
C9	0.0252 (14)	0.0237 (14)	0.0234 (14)	0.0007 (11)	0.0057 (12)	0.0085 (11)
C10	0.0324 (16)	0.0324 (16)	0.0271 (16)	0.0032 (13)	0.0025 (13)	0.0116 (13)
C11	0.0331 (17)	0.0439 (19)	0.046 (2)	0.0026 (15)	−0.0019 (15)	0.0262 (16)
C12	0.0329 (18)	0.0394 (19)	0.073 (3)	0.0131 (15)	0.0128 (18)	0.0329 (19)
C13	0.043 (2)	0.0264 (16)	0.062 (2)	0.0106 (15)	0.0213 (18)	0.0140 (16)
C14	0.0316 (16)	0.0244 (15)	0.0336 (17)	−0.0012 (12)	0.0078 (13)	0.0039 (12)
C15	0.0387 (18)	0.0331 (17)	0.0288 (16)	0.0081 (14)	−0.0004 (14)	−0.0004 (13)
Cl2	0.0602 (5)	0.0376 (4)	0.0227 (4)	0.0147 (4)	0.0028 (4)	0.0079 (3)
S2	0.0220 (4)	0.0284 (4)	0.0208 (4)	0.0028 (3)	0.0013 (3)	0.0037 (3)
O4	0.0357 (12)	0.0243 (10)	0.0332 (11)	0.0074 (9)	0.0082 (9)	0.0119 (9)
O5	0.0284 (11)	0.0342 (12)	0.0263 (11)	−0.0016 (9)	0.0059 (9)	0.0053 (9)
O6	0.0291 (11)	0.0441 (13)	0.0258 (11)	0.0092 (10)	−0.0025 (9)	0.0057 (9)
C16	0.0195 (14)	0.0266 (14)	0.0247 (14)	0.0060 (11)	0.0040 (11)	0.0054 (11)
C17	0.0191 (13)	0.0224 (14)	0.0255 (14)	0.0060 (11)	0.0042 (11)	0.0033 (11)
C18	0.0246 (14)	0.0217 (14)	0.0245 (14)	0.0040 (11)	0.0029 (12)	0.0051 (11)
C19	0.0316 (16)	0.0287 (15)	0.0229 (15)	0.0099 (12)	0.0046 (12)	0.0057 (12)
C20	0.0308 (16)	0.0271 (15)	0.0286 (16)	0.0059 (13)	−0.0029 (13)	−0.0023 (12)
C21	0.0296 (16)	0.0244 (15)	0.0378 (17)	0.0057 (12)	0.0035 (13)	0.0031 (13)
C22	0.0233 (14)	0.0239 (14)	0.0278 (15)	0.0075 (11)	0.0060 (12)	0.0074 (12)
C23	0.0282 (15)	0.0306 (16)	0.0282 (15)	0.0125 (12)	0.0084 (12)	0.0085 (12)
C24	0.0204 (14)	0.0215 (14)	0.0290 (15)	0.0004 (11)	−0.0008 (12)	0.0018 (11)
C25	0.0331 (16)	0.0329 (16)	0.0251 (15)	0.0065 (13)	0.0018 (13)	0.0011 (12)
C26	0.0364 (18)	0.0406 (19)	0.0387 (19)	0.0082 (15)	0.0091 (15)	−0.0068 (15)
C27	0.0289 (17)	0.0283 (17)	0.068 (3)	0.0069 (14)	0.0010 (17)	−0.0062 (16)
C28	0.0361 (18)	0.0215 (16)	0.072 (3)	0.0024 (14)	−0.0053 (18)	0.0160 (16)
C29	0.0304 (16)	0.0282 (16)	0.0431 (19)	−0.0012 (13)	0.0009 (14)	0.0155 (14)
C30	0.054 (2)	0.0414 (19)	0.0314 (17)	0.0169 (16)	0.0119 (15)	0.0183 (14)

Cl1—C4	1.750 (3)	Cl2—C19	1.746 (3)
S1—O3	1.437 (2)	S2—O6	1.437 (2)
S1—O2	1.437 (2)	S2—O5	1.438 (2)
S1—C1	1.746 (3)	S2—C16	1.742 (3)
S1—C9	1.762 (3)	S2—C24	1.762 (3)
O1—C8	1.369 (3)	O4—C23	1.368 (4)
O1—C7	1.375 (3)	O4—C22	1.378 (3)
C1—C8	1.357 (4)	C16—C23	1.361 (4)
C1—C2	1.451 (4)	C16—C17	1.452 (4)
C2—C7	1.386 (4)	C17—C22	1.392 (4)
C2—C3	1.404 (4)	C17—C18	1.395 (4)
C3—C4	1.383 (4)	C18—C19	1.386 (4)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.396 (4)	C19—C20	1.398 (4)
C5—C6	1.383 (4)	C20—C21	1.378 (4)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.383 (4)	C21—C22	1.386 (4)
C6—H6	0.9500	C21—H21	0.9500
C8—C15	1.484 (4)	C23—C30	1.480 (4)
C9—C10	1.388 (4)	C24—C29	1.383 (4)
C9—C14	1.391 (4)	C24—C25	1.389 (4)
C10—C11	1.391 (4)	C25—C26	1.377 (4)
C10—H10	0.9500	C25—H25	0.9500
C11—C12	1.375 (5)	C26—C27	1.382 (5)
C11—H11	0.9500	C26—H26	0.9500
C12—C13	1.374 (5)	C27—C28	1.374 (5)
C12—H12	0.9500	C27—H27	0.9500
C13—C14	1.389 (5)	C28—C29	1.388 (5)
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
O3—S1—O2	119.89 (13)	O6—S2—O5	119.93 (13)
O3—S1—C1	106.92 (13)	O6—S2—C16	108.60 (13)
O2—S1—C1	108.61 (13)	O5—S2—C16	107.16 (13)
O3—S1—C9	107.87 (13)	O6—S2—C24	107.79 (13)
O2—S1—C9	108.20 (13)	O5—S2—C24	108.08 (13)
C1—S1—C9	104.28 (13)	C16—S2—C24	104.18 (13)
C8—O1—C7	106.9 (2)	C23—O4—C22	106.9 (2)
C8—C1—C2	107.3 (2)	C23—C16—C17	107.4 (2)
C8—C1—S1	126.7 (2)	C23—C16—S2	127.1 (2)
C2—C1—S1	126.0 (2)	C17—C16—S2	125.5 (2)
C7—C2—C3	119.6 (2)	C22—C17—C18	119.4 (3)
C7—C2—C1	104.7 (2)	C22—C17—C16	104.4 (2)
C3—C2—C1	135.7 (3)	C18—C17—C16	136.2 (3)
C4—C3—C2	116.2 (3)	C19—C18—C17	116.5 (3)
C4—C3—H3	121.9	C19—C18—H18	121.7
C2—C3—H3	121.9	C17—C18—H18	121.7
C3—C4—C5	123.4 (3)	C18—C19—C20	123.5 (3)
C3—C4—Cl1	118.5 (2)	C18—C19—Cl2	118.9 (2)
C5—C4—Cl1	118.1 (2)	C20—C19—Cl2	117.6 (2)
C6—C5—C4	120.4 (3)	C21—C20—C19	120.0 (3)
C6—C5—H5	119.8	C21—C20—H20	120.0
C4—C5—H5	119.8	C19—C20—H20	120.0
C5—C6—C7	116.2 (3)	C20—C21—C22	116.5 (3)
C5—C6—H6	121.9	C20—C21—H21	121.7
C7—C6—H6	121.9	C22—C21—H21	121.7
O1—C7—C6	125.2 (3)	O4—C22—C21	125.3 (3)
O1—C7—C2	110.6 (2)	O4—C22—C17	110.7 (2)
C6—C7—C2	124.2 (3)	C21—C22—C17	124.0 (3)
C1—C8—O1	110.5 (2)	C16—C23—O4	110.6 (2)
C1—C8—C15	134.8 (3)	C16—C23—C30	134.7 (3)
O1—C8—C15	114.7 (3)	O4—C23—C30	114.7 (3)
C10—C9—C14	121.5 (3)	C29—C24—C25	121.4 (3)
C10—C9—S1	119.0 (2)	C29—C24—S2	120.0 (2)
C14—C9—S1	119.5 (2)	C25—C24—S2	118.5 (2)
C9—C10—C11	118.7 (3)	C26—C25—C24	119.4 (3)
C9—C10—H10	120.7	C26—C25—H25	120.3
C11—C10—H10	120.7	C24—C25—H25	120.3
C12—C11—C10	120.2 (3)	C25—C26—C27	119.6 (3)
C12—C11—H11	119.9	C25—C26—H26	120.2
C10—C11—H11	119.9	C27—C26—H26	120.2
C13—C12—C11	120.8 (3)	C28—C27—C26	120.8 (3)
C13—C12—H12	119.6	C28—C27—H27	119.6
C11—C12—H12	119.6	C26—C27—H27	119.6
C12—C13—C14	120.5 (3)	C27—C28—C29	120.5 (3)
C12—C13—H13	119.8	C27—C28—H28	119.7
C14—C13—H13	119.8	C29—C28—H28	119.7
C13—C14—C9	118.4 (3)	C24—C29—C28	118.3 (3)
C13—C14—H14	120.8	C24—C29—H29	120.9
C9—C14—H14	120.8	C28—C29—H29	120.9
C8—C15—H15A	109.5	C23—C30—H30A	109.5
C8—C15—H15B	109.5	C23—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C8—C15—H15C	109.5	C23—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5
O3—S1—C1—C8	−156.6 (2)	O6—S2—C16—C23	23.3 (3)
O2—S1—C1—C8	−25.9 (3)	O5—S2—C16—C23	154.3 (2)
C9—S1—C1—C8	89.3 (3)	C24—S2—C16—C23	−91.3 (3)
O3—S1—C1—C2	25.9 (3)	O6—S2—C16—C17	−159.3 (2)
O2—S1—C1—C2	156.6 (2)	O5—S2—C16—C17	−28.4 (3)
C9—S1—C1—C2	−88.2 (3)	C24—S2—C16—C17	86.0 (2)
C8—C1—C2—C7	0.8 (3)	C23—C16—C17—C22	−0.9 (3)
S1—C1—C2—C7	178.7 (2)	S2—C16—C17—C22	−178.7 (2)
C8—C1—C2—C3	179.8 (3)	C23—C16—C17—C18	179.9 (3)
S1—C1—C2—C3	−2.3 (5)	S2—C16—C17—C18	2.1 (5)
C7—C2—C3—C4	0.4 (4)	C22—C17—C18—C19	−1.0 (4)
C1—C2—C3—C4	−178.5 (3)	C16—C17—C18—C19	178.1 (3)
C2—C3—C4—C5	0.4 (4)	C17—C18—C19—C20	−0.2 (4)
C2—C3—C4—Cl1	179.1 (2)	C17—C18—C19—Cl2	−178.6 (2)
C3—C4—C5—C6	−0.7 (4)	C18—C19—C20—C21	0.9 (5)
Cl1—C4—C5—C6	−179.4 (2)	Cl2—C19—C20—C21	179.3 (2)
C4—C5—C6—C7	0.1 (4)	C19—C20—C21—C22	−0.3 (4)
C8—O1—C7—C6	−178.5 (3)	C23—O4—C22—C21	178.1 (3)
C8—O1—C7—C2	0.5 (3)	C23—O4—C22—C17	−0.2 (3)
C5—C6—C7—O1	179.6 (3)	C20—C21—C22—O4	−179.1 (3)
C5—C6—C7—C2	0.7 (4)	C20—C21—C22—C17	−1.0 (4)
C3—C2—C7—O1	−180.0 (2)	C18—C17—C22—O4	180.0 (2)
C1—C2—C7—O1	−0.8 (3)	C16—C17—C22—O4	0.6 (3)
C3—C2—C7—C6	−1.0 (4)	C18—C17—C22—C21	1.7 (4)
C1—C2—C7—C6	178.2 (3)	C16—C17—C22—C21	−177.7 (3)
C2—C1—C8—O1	−0.5 (3)	C17—C16—C23—O4	0.8 (3)
S1—C1—C8—O1	−178.42 (19)	S2—C16—C23—O4	178.58 (19)
C2—C1—C8—C15	177.8 (3)	C17—C16—C23—C30	−178.2 (3)
S1—C1—C8—C15	−0.1 (5)	S2—C16—C23—C30	−0.4 (5)
C7—O1—C8—C1	0.0 (3)	C22—O4—C23—C16	−0.4 (3)
C7—O1—C8—C15	−178.6 (2)	C22—O4—C23—C30	178.8 (2)
O3—S1—C9—C10	157.2 (2)	O6—S2—C24—C29	150.9 (2)
O2—S1—C9—C10	26.1 (3)	O5—S2—C24—C29	19.9 (3)
C1—S1—C9—C10	−89.4 (2)	C16—S2—C24—C29	−93.8 (3)
O3—S1—C9—C14	−25.0 (3)	O6—S2—C24—C25	−31.2 (3)
O2—S1—C9—C14	−156.0 (2)	O5—S2—C24—C25	−162.2 (2)
C1—S1—C9—C14	88.5 (2)	C16—S2—C24—C25	84.0 (2)
C14—C9—C10—C11	0.8 (4)	C29—C24—C25—C26	0.0 (4)
S1—C9—C10—C11	178.6 (2)	S2—C24—C25—C26	−177.8 (2)
C9—C10—C11—C12	−0.7 (4)	C24—C25—C26—C27	−0.1 (5)
C10—C11—C12—C13	0.6 (5)	C25—C26—C27—C28	0.0 (5)
C11—C12—C13—C14	−0.5 (5)	C26—C27—C28—C29	0.3 (5)
C12—C13—C14—C9	0.6 (5)	C25—C24—C29—C28	0.3 (4)
C10—C9—C14—C13	−0.7 (4)	S2—C24—C29—C28	178.0 (2)
S1—C9—C14—C13	−178.5 (2)	C27—C28—C29—C24	−0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2	0.98	2.44	3.153 (4)	130
C14—H14···O3i	0.95	2.51	3.429 (4)	164
C29—H29···O5ii	0.95	2.51	3.453 (4)	170
C30—H30A···O6	0.98	2.42	3.141 (4)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2	0.98	2.44	3.153 (4)	130
C14—H14⋯O3i	0.95	2.51	3.429 (4)	164
C29—H29⋯O5ii	0.95	2.51	3.453 (4)	170
C30—H30A⋯O6	0.98	2.42	3.141 (4)	130

Symmetry codes: (i) ; (ii) .