1,3-Bis{[(4-methyl-phen-yl)sulfon-yl]-oxy}propan-2-yl 4-methyl-benzene-sulfonate.

In the title sulfonate derivative, C(24)H(26)O(9)S(3), all atoms apart from those of one of the 4-methyl-benzene-sulfonate residues lie approximately in a disc; the dihedral angles between the approximately orthogonal benzene ring and those in the plane are 74.53 (9) and 67.79 (11)°. In the crystal, mol-ecules are consolidated into the three-dimensional architecture by C-H⋯O inter-actions. One of the 4-methyl-benzene-sulfonate residues is disordered over two almost parallel positions; the major component refined to a site-occupancy factor of 0.918 (2).

Related literature

For use of the title compound as a stabilizer for thermal recording materials, see: Matsumoto et al. (1996 ▶). For a related structure, see: Al-Mohammed et al. (2011 ▶).

Experimental

Crystal data

C24H26O9S3

M = 554.63

Triclinic,

a = 7.6887 (3) Å

b = 12.9635 (5) Å

c = 13.6887 (5) Å

α = 98.943 (3)°

β = 100.292 (3)°

γ = 105.174 (3)°

V = 1265.91 (8) Å3

Z = 2

Cu Kα radiation

μ = 3.13 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.407, T max = 0.508

9241 measured reflections

5191 independent reflections

4801 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.100

S = 1.06

5191 reflections

363 parameters

22 restraints

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.53 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008227/jj2124sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008227/jj2124Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008227/jj2124Isup3.cml

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

C24H26O9S3	Z = 2
Mr = 554.63	F(000) = 580
Triclinic, P1	Dx = 1.455 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.6887 (3) Å	Cell parameters from 5203 reflections
b = 12.9635 (5) Å	θ = 3.4–76.0°
c = 13.6887 (5) Å	µ = 3.13 mm−1
α = 98.943 (3)°	T = 100 K
β = 100.292 (3)°	Prism, colorless
γ = 105.174 (3)°	0.35 × 0.30 × 0.25 mm
V = 1265.91 (8) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	5191 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4801 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.018
Detector resolution: 10.4041 pixels mm-1	θmax = 76.2°, θmin = 3.4°
ω scan	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→16
Tmin = 0.407, Tmax = 0.508	l = −16→17
9241 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.5065P] where P = (Fo2 + 2Fc2)/3
5191 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.44 e Å−3
22 restraints	Δρmin = −0.53 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.49448 (5)	0.37561 (3)	0.65879 (3)	0.02049 (11)
S2	0.51107 (6)	0.76065 (4)	0.89915 (3)	0.02057 (14)	0.9178 (19)
O4	0.40477 (17)	0.66335 (10)	0.80445 (9)	0.0204 (3)	0.9178 (19)
O5	0.46255 (18)	0.71611 (11)	0.98305 (10)	0.0256 (3)	0.9178 (19)
O6	0.70049 (18)	0.79885 (12)	0.89449 (10)	0.0289 (3)	0.9178 (19)
S2'	0.5610 (6)	0.8258 (4)	0.8805 (3)	0.02057 (14)	0.08
O4'	0.5398 (17)	0.7696 (8)	0.7667 (6)	0.0204 (3)	0.08
O5'	0.497 (2)	0.7436 (11)	0.9354 (11)	0.0256 (3)	0.08
O6'	0.7505 (13)	0.8922 (11)	0.9127 (10)	0.0289 (3)	0.08
C11	0.4061 (3)	0.86328 (16)	0.88221 (14)	0.0214 (4)	0.9178 (19)
C12	0.5056 (3)	0.96078 (18)	0.86304 (14)	0.0258 (4)	0.9178 (19)
H12	0.6311	0.9727	0.8590	0.031*	0.9178 (19)
C13	0.4191 (3)	1.04095 (18)	0.84975 (15)	0.0294 (4)	0.9178 (19)
H13	0.4862	1.1078	0.8361	0.035*	0.9178 (19)
C14	0.2354 (3)	1.02465 (17)	0.85616 (16)	0.0282 (4)	0.9178 (19)
C15	0.1377 (5)	0.92566 (19)	0.8755 (3)	0.0283 (6)	0.9178 (19)
H15	0.0120	0.9134	0.8794	0.034*	0.9178 (19)
C16	0.2227 (3)	0.8451 (2)	0.8892 (3)	0.0258 (5)	0.9178 (19)
H16	0.1563	0.7783	0.9031	0.031*	0.9178 (19)
C17	0.1398 (4)	1.11140 (18)	0.83952 (17)	0.0377 (5)	0.9178 (19)
H17A	0.1399	1.1537	0.9054	0.057*	0.9178 (19)
H17B	0.0119	1.0761	0.8008	0.057*	0.9178 (19)
H17C	0.2061	1.1604	0.8016	0.057*	0.9178 (19)
C11'	0.418 (3)	0.9037 (19)	0.8732 (19)	0.0214 (4)	0.08
C12'	0.478 (3)	1.008 (2)	0.8559 (18)	0.0258 (4)	0.08
H12'	0.6025	1.0353	0.8506	0.031*	0.0822 (19)
C13'	0.366 (3)	1.0741 (18)	0.8462 (19)	0.0294 (4)	0.08
H13'	0.4131	1.1435	0.8308	0.035*	0.0822 (19)
C14'	0.186 (3)	1.0435 (19)	0.858 (2)	0.0282 (4)	0.08
C15'	0.133 (5)	0.942 (3)	0.888 (5)	0.0283 (6)	0.08
H15'	0.0250	0.9251	0.9139	0.034*	0.0822 (19)
C16'	0.231 (4)	0.869 (2)	0.880 (4)	0.0258 (5)	0.08
H16'	0.1739	0.7942	0.8799	0.031*	0.0822 (19)
C17'	0.056 (4)	1.114 (2)	0.863 (2)	0.0377 (5)	0.08
H17D	0.1152	1.1862	0.8505	0.057*	0.0822 (19)
H17E	0.0267	1.1227	0.9297	0.057*	0.0822 (19)
H17F	−0.0591	1.0787	0.8103	0.057*	0.0822 (19)
S3	−0.00968 (5)	0.71736 (3)	0.58851 (3)	0.02206 (11)
O1	0.43925 (15)	0.48154 (9)	0.69633 (9)	0.0210 (2)
O2	0.52903 (18)	0.37663 (11)	0.55959 (9)	0.0296 (3)
O3	0.35248 (16)	0.28856 (10)	0.67462 (10)	0.0288 (3)
O7	0.16164 (16)	0.70724 (10)	0.66600 (9)	0.0237 (2)
O8	−0.11727 (17)	0.75505 (11)	0.65271 (11)	0.0308 (3)
O9	−0.08818 (17)	0.61688 (10)	0.51449 (10)	0.0304 (3)
C1	0.5531 (2)	0.58641 (13)	0.68525 (13)	0.0223 (3)
H1A	0.5740	0.5812	0.6156	0.027*
H1B	0.6747	0.6093	0.7342	0.027*
C2	0.4473 (2)	0.66703 (14)	0.70636 (12)	0.0230 (3)
H2	0.5262	0.7423	0.7078	0.028*	0.9178 (19)
H2'	0.3914	0.6346	0.7594	0.028*	0.0822 (19)
C3	0.2684 (2)	0.64029 (14)	0.62715 (12)	0.0220 (3)
H3A	0.2944	0.6568	0.5621	0.026*
H3B	0.1993	0.5618	0.6154	0.026*
C4	0.7047 (2)	0.39166 (13)	0.74391 (12)	0.0201 (3)
C5	0.8713 (2)	0.44346 (14)	0.72137 (14)	0.0258 (3)
H5	0.8721	0.4721	0.6616	0.031*
C6	1.0356 (2)	0.45229 (15)	0.78773 (15)	0.0296 (4)
H6	1.1499	0.4873	0.7729	0.036*
C7	1.0371 (2)	0.41095 (14)	0.87563 (15)	0.0294 (4)
C8	0.8685 (3)	0.36109 (16)	0.89672 (15)	0.0328 (4)
H8	0.8677	0.3331	0.9568	0.039*
C9	0.7014 (2)	0.35129 (15)	0.83185 (14)	0.0271 (4)
H9	0.5871	0.3176	0.8474	0.033*
C10	1.2193 (3)	0.41970 (18)	0.94442 (19)	0.0421 (5)
H10A	1.2981	0.4959	0.9616	0.063*
H10B	1.2813	0.3732	0.9096	0.063*
H10C	1.1971	0.3958	1.0068	0.063*
C18	0.0922 (2)	0.82229 (13)	0.53146 (12)	0.0198 (3)
C19	0.1481 (2)	0.92984 (13)	0.58581 (13)	0.0230 (3)
H19	0.1269	0.9462	0.6520	0.028*
C20	0.2351 (2)	1.01301 (14)	0.54257 (14)	0.0261 (3)
H20	0.2727	1.0867	0.5792	0.031*
C21	0.2679 (2)	0.98960 (15)	0.44573 (14)	0.0269 (4)
C22	0.2096 (3)	0.88154 (16)	0.39294 (14)	0.0299 (4)
H22	0.2310	0.8649	0.3269	0.036*
C23	0.1207 (3)	0.79717 (15)	0.43453 (13)	0.0273 (4)
H23	0.0803	0.7236	0.3973	0.033*
C24	0.3618 (3)	1.08080 (18)	0.39891 (17)	0.0371 (4)
H24A	0.4166	1.1482	0.4513	0.056*
H24B	0.2704	1.0923	0.3452	0.056*
H24C	0.4592	1.0610	0.3698	0.056*

	U11	U22	U33	U12	U13	U23
S1	0.01969 (19)	0.01871 (19)	0.0219 (2)	0.00439 (15)	0.00552 (14)	0.00246 (14)
S2	0.0209 (2)	0.0224 (2)	0.0183 (2)	0.00569 (16)	0.00477 (16)	0.00529 (16)
O4	0.0244 (6)	0.0206 (6)	0.0175 (6)	0.0059 (5)	0.0077 (5)	0.0059 (5)
O5	0.0321 (7)	0.0287 (7)	0.0184 (6)	0.0096 (6)	0.0073 (5)	0.0090 (5)
O6	0.0200 (6)	0.0320 (7)	0.0309 (7)	0.0038 (5)	0.0038 (5)	0.0053 (6)
S2'	0.0209 (2)	0.0224 (2)	0.0183 (2)	0.00569 (16)	0.00477 (16)	0.00529 (16)
O4'	0.0244 (6)	0.0206 (6)	0.0175 (6)	0.0059 (5)	0.0077 (5)	0.0059 (5)
O5'	0.0321 (7)	0.0287 (7)	0.0184 (6)	0.0096 (6)	0.0073 (5)	0.0090 (5)
O6'	0.0200 (6)	0.0320 (7)	0.0309 (7)	0.0038 (5)	0.0038 (5)	0.0053 (6)
C11	0.0262 (9)	0.0190 (9)	0.0185 (8)	0.0058 (8)	0.0054 (6)	0.0032 (7)
C12	0.0289 (9)	0.0231 (10)	0.0230 (9)	0.0040 (9)	0.0067 (7)	0.0032 (7)
C13	0.0390 (12)	0.0195 (10)	0.0260 (9)	0.0042 (8)	0.0044 (8)	0.0051 (8)
C14	0.0389 (12)	0.0232 (10)	0.0186 (8)	0.0117 (8)	−0.0028 (9)	−0.0001 (7)
C15	0.0279 (9)	0.0284 (12)	0.0260 (16)	0.0091 (9)	0.0026 (8)	0.0015 (13)
C16	0.0246 (8)	0.0254 (13)	0.0268 (11)	0.0053 (9)	0.0063 (7)	0.0069 (10)
C17	0.0491 (14)	0.0290 (10)	0.0318 (11)	0.0166 (10)	−0.0024 (9)	0.0021 (8)
C11'	0.0262 (9)	0.0190 (9)	0.0185 (8)	0.0058 (8)	0.0054 (6)	0.0032 (7)
C12'	0.0289 (9)	0.0231 (10)	0.0230 (9)	0.0040 (9)	0.0067 (7)	0.0032 (7)
C13'	0.0390 (12)	0.0195 (10)	0.0260 (9)	0.0042 (8)	0.0044 (8)	0.0051 (8)
C14'	0.0389 (12)	0.0232 (10)	0.0186 (8)	0.0117 (8)	−0.0028 (9)	−0.0001 (7)
C15'	0.0279 (9)	0.0284 (12)	0.0260 (16)	0.0091 (9)	0.0026 (8)	0.0015 (13)
C16'	0.0246 (8)	0.0254 (13)	0.0268 (11)	0.0053 (9)	0.0063 (7)	0.0069 (10)
C17'	0.0491 (14)	0.0290 (10)	0.0318 (11)	0.0166 (10)	−0.0024 (9)	0.0021 (8)
S3	0.01781 (19)	0.0201 (2)	0.0277 (2)	0.00455 (14)	0.00356 (15)	0.00722 (15)
O1	0.0194 (5)	0.0187 (5)	0.0269 (6)	0.0051 (4)	0.0098 (4)	0.0065 (4)
O2	0.0333 (7)	0.0351 (7)	0.0205 (6)	0.0119 (5)	0.0077 (5)	0.0015 (5)
O3	0.0222 (6)	0.0202 (6)	0.0395 (7)	0.0006 (5)	0.0050 (5)	0.0051 (5)
O7	0.0247 (6)	0.0274 (6)	0.0212 (6)	0.0126 (5)	0.0034 (4)	0.0055 (5)
O8	0.0252 (6)	0.0324 (7)	0.0424 (7)	0.0118 (5)	0.0156 (5)	0.0157 (6)
O9	0.0252 (6)	0.0183 (6)	0.0396 (7)	0.0018 (5)	−0.0047 (5)	0.0041 (5)
C1	0.0182 (7)	0.0203 (8)	0.0282 (8)	0.0037 (6)	0.0061 (6)	0.0071 (6)
C2	0.0240 (8)	0.0219 (8)	0.0228 (8)	0.0073 (6)	0.0046 (6)	0.0043 (6)
C3	0.0233 (8)	0.0237 (8)	0.0217 (8)	0.0110 (6)	0.0047 (6)	0.0067 (6)
C4	0.0186 (7)	0.0178 (7)	0.0240 (8)	0.0056 (6)	0.0056 (6)	0.0035 (6)
C5	0.0242 (8)	0.0235 (8)	0.0318 (9)	0.0063 (7)	0.0120 (7)	0.0071 (7)
C6	0.0217 (8)	0.0249 (8)	0.0428 (10)	0.0054 (7)	0.0114 (7)	0.0069 (7)
C7	0.0239 (8)	0.0223 (8)	0.0393 (10)	0.0086 (7)	0.0012 (7)	0.0027 (7)
C8	0.0331 (9)	0.0344 (10)	0.0337 (10)	0.0113 (8)	0.0065 (8)	0.0145 (8)
C9	0.0253 (8)	0.0278 (8)	0.0297 (9)	0.0054 (7)	0.0099 (7)	0.0104 (7)
C10	0.0300 (10)	0.0362 (11)	0.0558 (13)	0.0129 (8)	−0.0044 (9)	0.0083 (9)
C18	0.0170 (7)	0.0202 (7)	0.0213 (7)	0.0056 (6)	0.0020 (6)	0.0049 (6)
C19	0.0214 (7)	0.0221 (8)	0.0228 (8)	0.0037 (6)	0.0055 (6)	0.0015 (6)
C20	0.0225 (8)	0.0199 (8)	0.0345 (9)	0.0047 (6)	0.0067 (7)	0.0045 (7)
C21	0.0230 (8)	0.0307 (9)	0.0342 (9)	0.0131 (7)	0.0096 (7)	0.0155 (7)
C22	0.0369 (9)	0.0356 (10)	0.0243 (8)	0.0171 (8)	0.0119 (7)	0.0107 (7)
C23	0.0338 (9)	0.0236 (8)	0.0240 (8)	0.0116 (7)	0.0040 (7)	0.0019 (6)
C24	0.0329 (10)	0.0400 (11)	0.0500 (12)	0.0156 (8)	0.0172 (9)	0.0267 (9)

S1—O3	1.4241 (13)	S3—O8	1.4258 (13)
S1—O2	1.4309 (12)	S3—O9	1.4308 (13)
S1—O1	1.5792 (11)	S3—O7	1.5848 (12)
S1—C4	1.7574 (16)	S3—C18	1.7506 (16)
S2—O5	1.4276 (13)	O1—C1	1.4581 (18)
S2—O6	1.4268 (14)	O7—C3	1.4478 (19)
S2—O4	1.5853 (13)	C1—C2	1.508 (2)
S2—C11	1.751 (2)	C1—H1A	0.9900
O4—C2	1.4424 (19)	C1—H1B	0.9900
S2'—O5'	1.432 (9)	C2—C3	1.513 (2)
S2'—O6'	1.433 (8)	C2—H2	1.0000
S2'—O4'	1.573 (7)	C2—H2'	1.0000
S2'—C11'	1.68 (2)	C3—H3A	0.9900
O4'—C2	1.382 (8)	C3—H3B	0.9900
C11—C12	1.386 (3)	C4—C9	1.387 (2)
C11—C16	1.391 (3)	C4—C5	1.394 (2)
C12—C13	1.390 (3)	C5—C6	1.384 (3)
C12—H12	0.9500	C5—H5	0.9500
C13—C14	1.393 (3)	C6—C7	1.391 (3)
C13—H13	0.9500	C6—H6	0.9500
C14—C15	1.398 (3)	C7—C8	1.390 (3)
C14—C17	1.519 (3)	C7—C10	1.509 (3)
C15—C16	1.387 (3)	C8—C9	1.389 (3)
C15—H15	0.9500	C8—H8	0.9500
C16—H16	0.9500	C9—H9	0.9500
C17—H17A	0.9800	C10—H10A	0.9800
C17—H17B	0.9800	C10—H10B	0.9800
C17—H17C	0.9800	C10—H10C	0.9800
C11'—C12'	1.382 (18)	C18—C23	1.387 (2)
C11'—C16'	1.416 (18)	C18—C19	1.390 (2)
C12'—C13'	1.370 (18)	C19—C20	1.387 (2)
C12'—H12'	0.9500	C19—H19	0.9500
C13'—C14'	1.377 (17)	C20—C21	1.396 (3)
C13'—H13'	0.9500	C20—H20	0.9500
C14'—C15'	1.412 (18)	C21—C22	1.388 (3)
C14'—C17'	1.529 (17)	C21—C24	1.511 (2)
C15'—C16'	1.365 (18)	C22—C23	1.389 (3)
C15'—H15'	0.9500	C22—H22	0.9500
C16'—H16'	0.9500	C23—H23	0.9500
C17'—H17D	0.9800	C24—H24A	0.9800
C17'—H17E	0.9800	C24—H24B	0.9800
C17'—H17F	0.9800	C24—H24C	0.9800
O3—S1—O2	120.39 (8)	O1—C1—C2	106.13 (12)
O3—S1—O1	104.08 (7)	O1—C1—H1A	110.5
O2—S1—O1	108.72 (7)	C2—C1—H1A	110.5
O3—S1—C4	109.80 (8)	O1—C1—H1B	110.5
O2—S1—C4	108.35 (8)	C2—C1—H1B	110.5
O1—S1—C4	104.29 (7)	H1A—C1—H1B	108.7
O5—S2—O6	120.42 (8)	O4'—C2—C1	119.5 (6)
O5—S2—O4	103.08 (7)	O4—C2—C1	108.20 (13)
O6—S2—O4	108.83 (8)	O4'—C2—C3	124.5 (6)
O5—S2—C11	109.48 (8)	O4—C2—C3	108.88 (13)
O6—S2—C11	109.22 (9)	C1—C2—C3	111.91 (14)
O4—S2—C11	104.56 (8)	O4—C2—H2	109.3
C2—O4—S2	120.41 (10)	C1—C2—H2	109.3
O5'—S2'—O6'	118.3 (9)	C3—C2—H2	109.3
O5'—S2'—O4'	109.3 (7)	O7—C3—C2	106.89 (13)
O6'—S2'—O4'	104.4 (7)	O7—C3—H3A	110.3
O5'—S2'—C11'	108.9 (11)	C2—C3—H3A	110.3
O6'—S2'—C11'	110.8 (11)	O7—C3—H3B	110.3
O4'—S2'—C11'	104.1 (10)	C2—C3—H3B	110.3
C2—O4'—S2'	135.1 (8)	H3A—C3—H3B	108.6
C12—C11—C16	121.07 (18)	C9—C4—C5	121.26 (16)
C12—C11—S2	120.16 (15)	C9—C4—S1	119.20 (13)
C16—C11—S2	118.77 (15)	C5—C4—S1	119.53 (13)
C11—C12—C13	119.08 (18)	C6—C5—C4	118.72 (16)
C11—C12—H12	120.5	C6—C5—H5	120.6
C13—C12—H12	120.5	C4—C5—H5	120.6
C12—C13—C14	120.92 (18)	C5—C6—C7	121.40 (16)
C12—C13—H13	119.5	C5—C6—H6	119.3
C14—C13—H13	119.5	C7—C6—H6	119.3
C15—C14—C13	119.0 (2)	C8—C7—C6	118.50 (16)
C15—C14—C17	120.1 (2)	C8—C7—C10	121.84 (18)
C13—C14—C17	120.9 (2)	C6—C7—C10	119.65 (18)
C16—C15—C14	120.6 (2)	C7—C8—C9	121.46 (17)
C16—C15—H15	119.7	C7—C8—H8	119.3
C14—C15—H15	119.7	C9—C8—H8	119.3
C15—C16—C11	119.3 (2)	C4—C9—C8	118.64 (16)
C15—C16—H16	120.3	C4—C9—H9	120.7
C11—C16—H16	120.3	C8—C9—H9	120.7
C12'—C11'—C16'	115.4 (17)	C7—C10—H10A	109.5
C12'—C11'—S2'	120.4 (18)	C7—C10—H10B	109.5
C16'—C11'—S2'	124.2 (18)	H10A—C10—H10B	109.5
C11'—C12'—C13'	122.9 (18)	C7—C10—H10C	109.5
C11'—C12'—H12'	118.6	H10A—C10—H10C	109.5
C13'—C12'—H12'	118.6	H10B—C10—H10C	109.5
C12'—C13'—C14'	122.4 (18)	C23—C18—C19	120.99 (15)
C12'—C13'—H13'	118.8	C23—C18—S3	119.93 (13)
C14'—C13'—H13'	118.8	C19—C18—S3	119.05 (12)
C13'—C14'—C15'	114.4 (18)	C20—C19—C18	119.37 (15)
C13'—C14'—C17'	128 (2)	C20—C19—H19	120.3
C15'—C14'—C17'	116.9 (19)	C18—C19—H19	120.3
C16'—C15'—C14'	122 (2)	C19—C20—C21	120.68 (16)
C14'—C15'—H15'	118.8	C19—C20—H20	119.7
C15'—C16'—C11'	120 (2)	C21—C20—H20	119.7
C15'—C16'—H16'	120.1	C22—C21—C20	118.71 (16)
C11'—C16'—H16'	120.1	C22—C21—C24	120.93 (17)
C14'—C17'—H17D	109.5	C20—C21—C24	120.34 (17)
C14'—C17'—H17E	109.5	C21—C22—C23	121.48 (16)
H17D—C17'—H17E	109.5	C21—C22—H22	119.3
C14'—C17'—H17F	109.5	C23—C22—H22	119.3
H17D—C17'—H17F	109.5	C18—C23—C22	118.74 (16)
H17E—C17'—H17F	109.5	C18—C23—H23	120.6
O8—S3—O9	120.40 (8)	C22—C23—H23	120.6
O8—S3—O7	103.60 (7)	C21—C24—H24A	109.5
O9—S3—O7	108.61 (7)	C21—C24—H24B	109.5
O8—S3—C18	109.66 (8)	H24A—C24—H24B	109.5
O9—S3—C18	110.02 (8)	C21—C24—H24C	109.5
O7—S3—C18	102.96 (7)	H24A—C24—H24C	109.5
C1—O1—S1	118.12 (9)	H24B—C24—H24C	109.5
C3—O7—S3	117.53 (10)
O5—S2—O4—C2	−167.25 (12)	S2'—O4'—C2—O4	0.7 (11)
O6—S2—O4—C2	−38.32 (14)	S2'—O4'—C2—C1	−101.6 (12)
C11—S2—O4—C2	78.29 (13)	S2'—O4'—C2—C3	103.1 (12)
O5'—S2'—O4'—C2	13.9 (16)	S2—O4—C2—O4'	−9.5 (6)
O6'—S2'—O4'—C2	141.3 (13)	S2—O4—C2—C1	107.04 (13)
C11'—S2'—O4'—C2	−102.3 (15)	S2—O4—C2—C3	−131.12 (12)
O5—S2—C11—C12	136.50 (15)	O1—C1—C2—O4'	136.3 (5)
O6—S2—C11—C12	2.71 (18)	O1—C1—C2—O4	54.53 (16)
O4—S2—C11—C12	−113.63 (15)	O1—C1—C2—C3	−65.43 (17)
O5—S2—C11—C16	−43.0 (2)	S3—O7—C3—C2	165.70 (10)
O6—S2—C11—C16	−176.8 (2)	O4'—C2—C3—O7	−34.9 (5)
O4—S2—C11—C16	66.9 (2)	O4—C2—C3—O7	48.53 (16)
C16—C11—C12—C13	−0.6 (3)	C1—C2—C3—O7	168.09 (13)
S2—C11—C12—C13	179.93 (15)	O3—S1—C4—C9	−21.13 (16)
C11—C12—C13—C14	0.4 (3)	O2—S1—C4—C9	−154.44 (14)
C12—C13—C14—C15	−0.5 (3)	O1—S1—C4—C9	89.88 (14)
C12—C13—C14—C17	−178.76 (19)	O3—S1—C4—C5	158.15 (13)
C13—C14—C15—C16	0.6 (5)	O2—S1—C4—C5	24.85 (15)
C17—C14—C15—C16	178.9 (3)	O1—S1—C4—C5	−90.84 (14)
C14—C15—C16—C11	−0.7 (5)	C9—C4—C5—C6	1.3 (3)
C12—C11—C16—C15	0.7 (4)	S1—C4—C5—C6	−177.99 (13)
S2—C11—C16—C15	−179.8 (3)	C4—C5—C6—C7	−0.1 (3)
O5'—S2'—C11'—C12'	158 (2)	C5—C6—C7—C8	−0.8 (3)
O6'—S2'—C11'—C12'	26 (2)	C5—C6—C7—C10	178.39 (17)
O4'—S2'—C11'—C12'	−85 (2)	C6—C7—C8—C9	0.5 (3)
O5'—S2'—C11'—C16'	−24 (3)	C10—C7—C8—C9	−178.60 (18)
O6'—S2'—C11'—C16'	−156 (3)	C5—C4—C9—C8	−1.5 (3)
O4'—S2'—C11'—C16'	92 (3)	S1—C4—C9—C8	177.78 (14)
C16'—C11'—C12'—C13'	0 (4)	C7—C8—C9—C4	0.6 (3)
S2'—C11'—C12'—C13'	178 (2)	O8—S3—C18—C23	−147.39 (14)
C11'—C12'—C13'—C14'	3 (4)	O9—S3—C18—C23	−12.79 (16)
C12'—C13'—C14'—C15'	4 (5)	O7—S3—C18—C23	102.83 (14)
C12'—C13'—C14'—C17'	172 (3)	O8—S3—C18—C19	34.45 (15)
C13'—C14'—C15'—C16'	−16 (7)	O9—S3—C18—C19	169.05 (12)
C17'—C14'—C15'—C16'	175 (5)	O7—S3—C18—C19	−75.33 (14)
C14'—C15'—C16'—C11'	20 (8)	C23—C18—C19—C20	−0.5 (2)
C12'—C11'—C16'—C15'	−11 (6)	S3—C18—C19—C20	177.62 (12)
S2'—C11'—C16'—C15'	171 (4)	C18—C19—C20—C21	−0.5 (3)
O3—S1—O1—C1	−176.79 (11)	C19—C20—C21—C22	0.8 (3)
O2—S1—O1—C1	−47.32 (13)	C19—C20—C21—C24	179.63 (16)
C4—S1—O1—C1	68.10 (12)	C20—C21—C22—C23	−0.2 (3)
O8—S3—O7—C3	161.56 (11)	C24—C21—C22—C23	−179.03 (17)
O9—S3—O7—C3	32.45 (13)	C19—C18—C23—C22	1.1 (3)
C18—S3—O7—C3	−84.18 (12)	S3—C18—C23—C22	−177.02 (13)
S1—O1—C1—C2	168.60 (10)	C21—C22—C23—C18	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	0.99	2.58	3.430 (2)	144
C3—H3A···O2i	0.99	2.39	3.230 (2)	143
C3—H3B···O9ii	0.99	2.53	3.377 (2)	144
C6—H6···O4iii	0.95	2.51	3.332 (2)	145
C9—H9···O5iv	0.95	2.50	3.166 (2)	127
C15—H15···O6v	0.95	2.53	3.409 (4)	154
C20—H20···O3vi	0.95	2.60	3.545 (2)	176
C24—H24B···O8vii	0.98	2.55	3.263 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	0.99	2.58	3.430 (2)	144
C3—H3A⋯O2i	0.99	2.39	3.230 (2)	143
C3—H3B⋯O9ii	0.99	2.53	3.377 (2)	144
C6—H6⋯O4iii	0.95	2.51	3.332 (2)	145
C9—H9⋯O5iv	0.95	2.50	3.166 (2)	127
C15—H15⋯O6v	0.95	2.53	3.409 (4)	154
C20—H20⋯O3vi	0.95	2.60	3.545 (2)	176
C24—H24B⋯O8vii	0.98	2.55	3.263 (3)	129

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .