4,4'-[4,4'-Sulfonyl-bis-(p-phenyl-ene-oxy)]dibutanoic acid.

In the title compound, C(20)H(22)O(8)S, the dihedral angle between the two benzene rings is 81.6 (3)°. The benzene-connected portions of the alk-oxy substituents are almost coplanar with their respective rings [C-C-O-C torsion angles of 174.77 (17) and -178.5 (4)°]. One of the butanoic acid groups is disordered over two conformations with a site-occupancy ratio 0.719 (6):0.281 (6). In the crystal, pairs of O-H⋯O hydrogen bonds link the mol-ecules into infinite zigzag chains along [130].

Related literature

For bis­phenol S (systematic name 4,4′-sulfonyl­diphenol) as a reactant in ep­oxy reactions and its use in fast-curing ep­oxy resin glues, see: Askarinejad & Morsali (2006 ▶); Danzl et al. (2009 ▶); Bashiri et al. (2009 ▶). For its use in the manufacture of pharmaceuticals, adhesives, biocides and agricultural products, see: Howard & David (2002 ▶); Howard et al. (2005 ▶); Yasue et al. (2009 ▶). For synthesis details and a related structure, see: Zheng et al. (2007 ▶).

Experimental

Crystal data

C20H22O8S

M = 422.45

Monoclinic,

a = 30.945 (7) Å

b = 8.0964 (18) Å

c = 16.032 (3) Å

β = 94.711 (5)°

V = 4003.1 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.20 × 0.18 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.975

12299 measured reflections

4362 independent reflections

2927 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.139

S = 1.00

4362 reflections

327 parameters

19 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011871/pk2315sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011871/pk2315Isup2.hkl

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

C20H22O8S	F(000) = 1776
Mr = 422.45	Dx = 1.402 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2472 reflections
a = 30.945 (7) Å	θ = 2.6–23.6°
b = 8.0964 (18) Å	µ = 0.21 mm−1
c = 16.032 (3) Å	T = 296 K
β = 94.711 (5)°	Block, colorless
V = 4003.1 (15) Å3	0.20 × 0.18 × 0.12 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	4362 independent reflections
Radiation source: fine-focus sealed tube	2927 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 27.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −39→35
Tmin = 0.959, Tmax = 0.975	k = −10→8
12299 measured reflections	l = −20→20

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.076P)2] where P = (Fo2 + 2Fc2)/3
4362 reflections	(Δ/σ)max < 0.001
327 parameters	Δρmax = 0.30 e Å−3
19 restraints	Δρmin = −0.21 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 > 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	Occ. (<1)
S1	0.340925 (17)	0.09320 (6)	0.19395 (3)	0.04130 (18)
O1	0.21477 (5)	0.09741 (18)	0.44895 (9)	0.0480 (4)
O2	0.13002 (5)	−0.23795 (19)	0.54170 (11)	0.0623 (5)
O3	0.08084 (6)	−0.0961 (2)	0.46295 (12)	0.0643 (5)
H3	0.0708	−0.1887	0.4537	0.096*
O4	0.31868 (5)	0.1453 (2)	0.11609 (9)	0.0593 (5)
O5	0.36503 (5)	−0.05895 (19)	0.19703 (11)	0.0557 (4)
C1	0.21744 (7)	−0.0104 (3)	0.52061 (13)	0.0467 (5)
H1A	0.2459	−0.0025	0.5507	0.056*
H1B	0.2126	−0.1240	0.5031	0.056*
C2	0.18298 (7)	0.0436 (3)	0.57577 (14)	0.0512 (6)
H2A	0.1909	0.1511	0.5990	0.061*
H2B	0.1826	−0.0333	0.6221	0.061*
C3	0.13776 (7)	0.0545 (3)	0.53276 (15)	0.0462 (5)
H3A	0.1198	0.1173	0.5682	0.055*
H3B	0.1391	0.1158	0.4811	0.055*
C4	0.11608 (7)	−0.1071 (3)	0.51281 (13)	0.0425 (5)
C5	0.24467 (6)	0.0837 (2)	0.39240 (13)	0.0374 (5)
C6	0.28269 (6)	−0.0081 (2)	0.40364 (13)	0.0404 (5)
H6	0.2888	−0.0694	0.4522	0.049*
C7	0.31147 (6)	−0.0073 (2)	0.34153 (13)	0.0401 (5)
H7	0.3369	−0.0687	0.3486	0.048*
C8	0.30262 (6)	0.0842 (2)	0.26918 (12)	0.0354 (4)
C9	0.26422 (6)	0.1752 (3)	0.25765 (13)	0.0419 (5)
H9	0.2581	0.2361	0.2089	0.050*
C10	0.23556 (7)	0.1743 (3)	0.31866 (13)	0.0431 (5)
H10	0.2099	0.2342	0.3109	0.052*
O6	0.45017 (16)	0.6539 (4)	0.3091 (3)	0.0555 (9)	0.719 (6)
O7	0.54917 (16)	1.1033 (5)	0.4276 (4)	0.0632 (11)	0.719 (6)
O8	0.59897 (13)	0.9699 (5)	0.5104 (3)	0.0758 (11)	0.719 (6)
H8A	0.6081	1.0636	0.5201	0.114*	0.719 (6)
C11	0.48910 (17)	0.6369 (5)	0.3610 (3)	0.0527 (11)	0.719 (6)
H11A	0.5100	0.5720	0.3332	0.063*	0.719 (6)
H11B	0.4836	0.5824	0.4130	0.063*	0.719 (6)
C12	0.50608 (12)	0.8096 (5)	0.3780 (2)	0.0552 (11)	0.719 (6)
H12A	0.5116	0.8619	0.3255	0.066*	0.719 (6)
H12B	0.4843	0.8742	0.4035	0.066*	0.719 (6)
C13	0.54702 (12)	0.8074 (4)	0.4348 (3)	0.0611 (12)	0.719 (6)
H13A	0.5415	0.7517	0.4864	0.073*	0.719 (6)
H13B	0.5688	0.7442	0.4084	0.073*	0.719 (6)
C14	0.5647 (2)	0.9760 (8)	0.4554 (5)	0.0500 (13)	0.719 (6)
O6B	0.4601 (3)	0.6099 (11)	0.3342 (8)	0.056 (3)	0.281 (6)
O7B	0.5371 (4)	1.1472 (15)	0.4022 (10)	0.079 (3)	0.281 (6)
O8B	0.5816 (5)	0.9780 (14)	0.4772 (8)	0.077 (5)	0.281 (6)
H8B	0.5954	1.0583	0.4958	0.115*	0.281 (6)
C11B	0.4986 (3)	0.5743 (13)	0.3876 (7)	0.052 (3)	0.281 (6)
H11C	0.5204	0.5281	0.3544	0.063*	0.281 (6)
H11D	0.4919	0.4925	0.4289	0.063*	0.281 (6)
C12B	0.5164 (3)	0.7285 (11)	0.4321 (6)	0.064 (3)	0.281 (6)
H12C	0.4938	0.7772	0.4627	0.076*	0.281 (6)
H12D	0.5400	0.6969	0.4725	0.076*	0.281 (6)
C13B	0.5326 (5)	0.8560 (13)	0.3745 (7)	0.086 (4)	0.281 (6)
H13C	0.5088	0.8878	0.3345	0.103*	0.281 (6)
H13D	0.5548	0.8061	0.3434	0.103*	0.281 (6)
C14B	0.5511 (5)	1.0101 (16)	0.4168 (9)	0.070 (5)	0.281 (6)
C15	0.42950 (8)	0.5072 (3)	0.28884 (15)	0.0543 (6)
C16	0.39020 (8)	0.5418 (3)	0.24433 (16)	0.0583 (7)
H16	0.3818	0.6508	0.2345	0.070*
C17	0.36394 (7)	0.4158 (3)	0.21499 (14)	0.0481 (5)
H17	0.3376	0.4389	0.1850	0.058*
C18	0.37640 (6)	0.2527 (2)	0.22985 (12)	0.0373 (4)
C19	0.41573 (7)	0.2172 (3)	0.27360 (13)	0.0452 (5)
H19	0.4241	0.1080	0.2831	0.054*
C20	0.44257 (7)	0.3452 (3)	0.30315 (14)	0.0530 (6)
H20	0.4691	0.3225	0.3323	0.064*

	U11	U22	U33	U12	U13	U23
S1	0.0421 (3)	0.0388 (3)	0.0425 (3)	−0.0041 (2)	0.0004 (2)	−0.0036 (2)
O1	0.0396 (8)	0.0491 (9)	0.0560 (9)	0.0045 (7)	0.0085 (7)	0.0140 (7)
O2	0.0677 (11)	0.0382 (9)	0.0787 (12)	0.0006 (8)	−0.0076 (9)	0.0096 (8)
O3	0.0564 (10)	0.0474 (10)	0.0850 (12)	−0.0063 (8)	−0.0190 (9)	0.0033 (9)
O4	0.0603 (10)	0.0783 (12)	0.0377 (8)	−0.0082 (9)	−0.0060 (7)	0.0012 (8)
O5	0.0559 (10)	0.0374 (9)	0.0750 (11)	0.0022 (7)	0.0126 (8)	−0.0089 (8)
C1	0.0389 (11)	0.0539 (14)	0.0462 (12)	−0.0021 (10)	−0.0034 (9)	0.0087 (10)
C2	0.0507 (13)	0.0572 (14)	0.0459 (12)	−0.0099 (11)	0.0050 (10)	−0.0076 (11)
C3	0.0445 (12)	0.0394 (12)	0.0558 (13)	−0.0019 (9)	0.0106 (10)	−0.0012 (10)
C4	0.0415 (12)	0.0422 (12)	0.0444 (12)	−0.0025 (10)	0.0066 (9)	−0.0025 (10)
C5	0.0324 (10)	0.0319 (11)	0.0474 (11)	−0.0065 (8)	−0.0010 (9)	0.0031 (9)
C6	0.0397 (11)	0.0354 (11)	0.0447 (11)	−0.0013 (9)	−0.0058 (9)	0.0095 (9)
C7	0.0332 (10)	0.0347 (11)	0.0508 (12)	0.0021 (9)	−0.0057 (9)	0.0044 (9)
C8	0.0331 (10)	0.0315 (10)	0.0405 (10)	−0.0057 (8)	−0.0032 (8)	−0.0007 (8)
C9	0.0394 (11)	0.0386 (11)	0.0457 (12)	−0.0025 (9)	−0.0084 (9)	0.0092 (9)
C10	0.0334 (11)	0.0372 (11)	0.0571 (13)	0.0022 (9)	−0.0050 (9)	0.0101 (10)
O6	0.051 (2)	0.0397 (19)	0.073 (3)	−0.0119 (16)	−0.0064 (15)	0.0036 (16)
O7	0.056 (3)	0.048 (3)	0.081 (3)	−0.006 (2)	−0.0220 (18)	0.000 (2)
O8	0.082 (3)	0.0502 (15)	0.087 (3)	−0.0161 (15)	−0.0477 (19)	0.0065 (18)
C11	0.057 (3)	0.053 (3)	0.049 (3)	−0.012 (2)	0.008 (2)	−0.001 (2)
C12	0.052 (2)	0.053 (2)	0.059 (2)	−0.0150 (18)	−0.0059 (18)	0.0000 (19)
C13	0.061 (3)	0.044 (2)	0.075 (3)	−0.0112 (18)	−0.0126 (19)	0.0000 (19)
C14	0.058 (4)	0.048 (2)	0.042 (4)	−0.011 (3)	−0.009 (3)	−0.004 (3)
O6B	0.054 (6)	0.028 (4)	0.084 (8)	−0.009 (4)	−0.009 (5)	0.004 (4)
O7B	0.069 (8)	0.061 (7)	0.105 (10)	−0.006 (5)	−0.011 (6)	−0.003 (6)
O8B	0.107 (14)	0.047 (5)	0.069 (9)	−0.023 (8)	−0.042 (6)	−0.001 (5)
C11B	0.049 (6)	0.044 (6)	0.061 (7)	−0.022 (5)	−0.013 (5)	−0.001 (5)
C12B	0.048 (6)	0.073 (7)	0.070 (7)	−0.009 (5)	0.005 (5)	−0.007 (6)
C13B	0.100 (11)	0.084 (8)	0.074 (8)	−0.035 (8)	0.015 (8)	−0.011 (7)
C14B	0.079 (10)	0.092 (13)	0.036 (7)	−0.024 (10)	−0.005 (6)	0.002 (8)
C15	0.0582 (14)	0.0433 (14)	0.0644 (15)	−0.0223 (12)	0.0231 (12)	−0.0135 (11)
C16	0.0601 (16)	0.0348 (12)	0.0825 (18)	−0.0020 (11)	0.0216 (14)	0.0016 (12)
C17	0.0453 (12)	0.0410 (12)	0.0583 (14)	0.0002 (10)	0.0056 (11)	0.0098 (10)
C18	0.0347 (10)	0.0362 (11)	0.0413 (11)	−0.0035 (9)	0.0058 (8)	0.0018 (9)
C19	0.0405 (12)	0.0384 (12)	0.0557 (13)	−0.0010 (9)	−0.0008 (10)	0.0024 (10)
C20	0.0394 (12)	0.0610 (15)	0.0581 (14)	−0.0110 (11)	0.0003 (10)	−0.0038 (12)

S1—O4	1.4383 (15)	C11—H11A	0.9700
S1—O5	1.4389 (17)	C11—H11B	0.9700
S1—C8	1.761 (2)	C12—C13	1.498 (4)
S1—C18	1.761 (2)	C12—H12A	0.9700
O1—C5	1.352 (2)	C12—H12B	0.9700
O1—C1	1.440 (2)	C13—C14	1.497 (6)
O2—C4	1.221 (3)	C13—H13A	0.9700
O3—C4	1.301 (3)	C13—H13B	0.9700
O3—H3	0.8200	C14—H8B	1.2897
C1—C2	1.505 (3)	O6B—C15	1.416 (7)
C1—H1A	0.9700	O6B—C11B	1.436 (8)
C1—H1B	0.9700	O7B—C14B	1.208 (12)
C2—C3	1.511 (3)	O8B—C14B	1.321 (11)
C2—H2A	0.9700	O8B—H8A	1.2384
C2—H2B	0.9700	O8B—H8B	0.8200
C3—C4	1.493 (3)	C11B—C12B	1.519 (7)
C3—H3A	0.9700	C11B—H11C	0.9700
C3—H3B	0.9700	C11B—H11D	0.9700
C5—C6	1.391 (3)	C12B—C13B	1.498 (7)
C5—C10	1.400 (3)	C12B—H12C	0.9700
C6—C7	1.390 (3)	C12B—H12D	0.9700
C6—H6	0.9300	C13B—C14B	1.510 (8)
C7—C8	1.384 (3)	C13B—H13C	0.9700
C7—H7	0.9300	C13B—H13D	0.9700
C8—C9	1.398 (3)	C15—C20	1.386 (4)
C9—C10	1.373 (3)	C15—C16	1.387 (4)
C9—H9	0.9300	C16—C17	1.364 (3)
C10—H10	0.9300	C16—H16	0.9300
O6—C15	1.375 (4)	C17—C18	1.390 (3)
O6—C11	1.413 (5)	C17—H17	0.9300
O7—C14	1.207 (8)	C18—C19	1.384 (3)
O8—C14	1.323 (7)	C19—C20	1.387 (3)
O8—H8A	0.8199	C19—H19	0.9300
O8—H8B	0.7586	C20—H20	0.9300
C11—C12	1.510 (5)
O4—S1—O5	119.39 (10)	C13—C12—H12B	109.4
O4—S1—C8	107.79 (9)	C11—C12—H12B	109.4
O5—S1—C8	108.49 (10)	H12A—C12—H12B	108.0
O4—S1—C18	108.03 (10)	C14—C13—C12	113.5 (4)
O5—S1—C18	108.01 (10)	C14—C13—H13A	108.9
C8—S1—C18	104.08 (9)	C12—C13—H13A	108.9
C5—O1—C1	119.19 (15)	C14—C13—H13B	108.9
C4—O3—H3	109.5	C12—C13—H13B	108.9
O1—C1—C2	107.20 (18)	H13A—C13—H13B	107.7
O1—C1—H1A	110.3	O7—C14—O8	123.4 (5)
C2—C1—H1A	110.3	O7—C14—C13	124.7 (6)
O1—C1—H1B	110.3	O8—C14—C13	111.8 (6)
C2—C1—H1B	110.3	O7—C14—H8B	89.9
H1A—C1—H1B	108.5	C13—C14—H8B	145.3
C1—C2—C3	115.04 (18)	C15—O6B—C11B	132.5 (7)
C1—C2—H2A	108.5	C14B—O8B—H8A	134.2
C3—C2—H2A	108.5	C14B—O8B—H8B	115.4
C1—C2—H2B	108.5	O6B—C11B—C12B	111.5 (8)
C3—C2—H2B	108.5	O6B—C11B—H11C	109.3
H2A—C2—H2B	107.5	C12B—C11B—H11C	109.3
C4—C3—C2	115.44 (19)	O6B—C11B—H11D	109.3
C4—C3—H3A	108.4	C12B—C11B—H11D	109.3
C2—C3—H3A	108.4	H11C—C11B—H11D	108.0
C4—C3—H3B	108.4	C13B—C12B—C11B	113.9 (8)
C2—C3—H3B	108.4	C13B—C12B—H12C	108.8
H3A—C3—H3B	107.5	C11B—C12B—H12C	108.8
O2—C4—O3	123.0 (2)	C13B—C12B—H12D	108.8
O2—C4—C3	122.7 (2)	C11B—C12B—H12D	108.8
O3—C4—C3	114.26 (19)	H12C—C12B—H12D	107.7
O1—C5—C6	125.11 (18)	C12B—C13B—C14B	115.3 (10)
O1—C5—C10	114.95 (17)	C12B—C13B—H13C	108.5
C6—C5—C10	119.93 (19)	C14B—C13B—H13C	108.5
C7—C6—C5	119.33 (18)	C12B—C13B—H13D	108.5
C7—C6—H6	120.3	C14B—C13B—H13D	108.5
C5—C6—H6	120.3	H13C—C13B—H13D	107.5
C8—C7—C6	120.56 (18)	O7B—C14B—O8B	123.1 (12)
C8—C7—H7	119.7	O7B—C14B—C13B	123.7 (13)
C6—C7—H7	119.7	O8B—C14B—C13B	112.9 (13)
C7—C8—C9	120.04 (19)	O6—C15—C20	130.9 (3)
C7—C8—S1	119.87 (15)	O6—C15—C16	108.6 (3)
C9—C8—S1	120.02 (15)	C20—C15—C16	120.5 (2)
C10—C9—C8	119.64 (18)	C20—C15—O6B	107.2 (4)
C10—C9—H9	120.2	C16—C15—O6B	131.9 (5)
C8—C9—H9	120.2	C17—C16—C15	119.9 (2)
C9—C10—C5	120.49 (19)	C17—C16—H16	120.0
C9—C10—H10	119.8	C15—C16—H16	120.0
C5—C10—H10	119.8	C16—C17—C18	120.2 (2)
C15—O6—C11	114.4 (3)	C16—C17—H17	119.9
C14—O8—H8A	109.7	C18—C17—H17	119.9
C14—O8—H8B	70.7	C19—C18—C17	120.29 (19)
O6—C11—C12	106.4 (4)	C19—C18—S1	120.77 (16)
O6—C11—H11A	110.4	C17—C18—S1	118.93 (16)
C12—C11—H11A	110.4	C18—C19—C20	119.6 (2)
O6—C11—H11B	110.4	C18—C19—H19	120.2
C12—C11—H11B	110.4	C20—C19—H19	120.2
H11A—C11—H11B	108.6	C15—C20—C19	119.5 (2)
C13—C12—C11	111.3 (4)	C15—C20—H20	120.3
C13—C12—H12A	109.4	C19—C20—H20	120.3
C11—C12—H12A	109.4
C5—O1—C1—C2	174.77 (17)	O6B—C11B—C12B—C13B	−65.6 (15)
O1—C1—C2—C3	53.5 (3)	C11B—C12B—C13B—C14B	−179.2 (11)
C1—C2—C3—C4	73.3 (3)	C12B—C13B—C14B—O7B	−120.5 (19)
C2—C3—C4—O2	12.6 (3)	C12B—C13B—C14B—O8B	53.2 (19)
C2—C3—C4—O3	−168.2 (2)	C11—O6—C15—C20	−7.8 (7)
C1—O1—C5—C6	−11.3 (3)	C11—O6—C15—C16	174.8 (4)
C1—O1—C5—C10	170.19 (18)	C11—O6—C15—O6B	13.3 (16)
O1—C5—C6—C7	−177.81 (18)	C11B—O6B—C15—O6	−164 (3)
C10—C5—C6—C7	0.6 (3)	C11B—O6B—C15—C20	−0.3 (17)
C5—C6—C7—C8	0.2 (3)	C11B—O6B—C15—C16	172.4 (11)
C6—C7—C8—C9	−0.8 (3)	O6—C15—C16—C17	178.3 (3)
C6—C7—C8—S1	176.31 (15)	C20—C15—C16—C17	0.6 (4)
O4—S1—C8—C7	160.76 (16)	O6B—C15—C16—C17	−171.4 (8)
O5—S1—C8—C7	30.16 (18)	C15—C16—C17—C18	0.2 (4)
C18—S1—C8—C7	−84.68 (17)	C16—C17—C18—C19	−0.8 (3)
O4—S1—C8—C9	−22.18 (19)	C16—C17—C18—S1	177.98 (17)
O5—S1—C8—C9	−152.77 (16)	O4—S1—C18—C19	−146.43 (17)
C18—S1—C8—C9	92.39 (17)	O5—S1—C18—C19	−16.0 (2)
C7—C8—C9—C10	0.4 (3)	C8—S1—C18—C19	99.18 (18)
S1—C8—C9—C10	−176.62 (15)	O4—S1—C18—C17	34.8 (2)
C8—C9—C10—C5	0.4 (3)	O5—S1—C18—C17	165.25 (17)
O1—C5—C10—C9	177.64 (18)	C8—S1—C18—C17	−79.57 (19)
C6—C5—C10—C9	−1.0 (3)	C17—C18—C19—C20	0.5 (3)
C15—O6—C11—C12	−178.5 (4)	S1—C18—C19—C20	−178.27 (16)
O6—C11—C12—C13	178.5 (4)	O6—C15—C20—C19	−178.0 (4)
C11—C12—C13—C14	−178.6 (4)	C16—C15—C20—C19	−0.9 (4)
C12—C13—C14—O7	−2.6 (9)	O6B—C15—C20—C19	172.8 (6)
C12—C13—C14—O8	175.4 (5)	C18—C19—C20—C15	0.4 (3)
C15—O6B—C11B—C12B	−171.3 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O8B—H8B···O2i	0.82	2.07	2.890 (11)	180
O8—H8A···O2i	0.82	1.77	2.587 (4)	178
O3—H3···O7Bii	0.82	1.84	2.623 (13)	159
O3—H3···O7ii	0.82	1.85	2.668 (5)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8B—H8B⋯O2i	0.82	2.07	2.890 (11)	180
O8—H8A⋯O2i	0.82	1.77	2.587 (4)	178
O3—H3⋯O7Bii	0.82	1.84	2.623 (13)	159
O3—H3⋯O7ii	0.82	1.85	2.668 (5)	177

Symmetry codes: (i) ; (ii) .