Tetra-O-4-methyl-phenyl-sulfonyl-penta-erythritol.

In the title mol-ecule (systematic name: methane-tetra-yltetra-methyl-ene tetra-p-toluene-sulfonate), C(33)H(36)O(12)S(4), the central C atom and the S atoms exhibit distorted tetra-hedral configurations. The aromatic rings in opposite arms are nearly parallel to each other, with a dihedral angle of 10.26 (8) or 3.45 (9)°. The mol-ecules are linked into a two-dimensional network parallel to the bc plane by weak C-H⋯O hydrogen bonds, π-π [centroid-centroid distance = 3.5806 (12) Å] and S-O⋯π [O⋯centroid = 3.1455 (15) Å and S-O⋯centroid = 122.41 (7)°] inter-molecular inter-actions. Intramolecular C-H⋯O hydrogen bonds are also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Li et al. (2008 ▶). For general background and applications of penta­erythritol derivatives, see: Constable et al. (1998 ▶); Fundueanu et al. (1998 ▶); Jiang et al. (2002 ▶); Kim et al. (2000 ▶); Luo & Chen (2001 ▶); Mischiati et al. (2001 ▶); Oike et al. (2001 ▶).

Experimental

Crystal data

C33H36O12S4

M = 752.86

Monoclinic,

a = 13.2983 (2) Å

b = 18.0368 (2) Å

c = 15.4181 (2) Å

β = 110.653 (1)°

V = 3460.50 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 100.0 (1) K

0.47 × 0.41 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.857, T max = 0.949

45048 measured reflections

10090 independent reflections

7927 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.04

10090 reflections

446 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020643/ci2625sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020643/ci2625Isup2.hkl

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

C33H36O12S4	F000 = 1576
Mr = 752.86	Dx = 1.445 Mg m−3
Monoclinic, P21/c	Melting point: 423 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 13.2983 (2) Å	Cell parameters from 10090 reflections
b = 18.0368 (2) Å	θ = 1.8–30.0º
c = 15.4181 (2) Å	µ = 0.34 mm−1
β = 110.653 (1)º	T = 100.0 (1) K
V = 3460.50 (8) Å3	Block, colourless
Z = 4	0.47 × 0.41 × 0.16 mm

Bruker SMART APEXII CCD area-detector diffractometer	10090 independent reflections
Radiation source: fine-focus sealed tube	7927 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 1.8º
ω scans	h = −18→17
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −25→25
Tmin = 0.857, Tmax = 0.949	l = −21→21
45048 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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0595P)2 + 1.2746P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
10090 reflections	Δρmax = 0.66 e Å−3
446 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temparture data was collected with the Oxford Cryosystem Cobra low-temperature attachment.

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 > 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
S1	0.04280 (3)	0.38393 (2)	0.37155 (3)	0.01965 (9)
S2	0.41959 (4)	0.31806 (2)	0.71340 (3)	0.02583 (10)
S3	0.16570 (3)	0.37598 (2)	0.89436 (3)	0.02097 (9)
S4	−0.18947 (4)	0.29379 (2)	0.54246 (3)	0.02429 (10)
O1	0.06272 (10)	0.34535 (6)	0.46843 (7)	0.0207 (2)
O2	−0.01854 (10)	0.45006 (6)	0.36647 (8)	0.0249 (2)
O3	0.00233 (10)	0.32556 (7)	0.30634 (8)	0.0267 (3)
O4	0.30102 (10)	0.34530 (6)	0.65781 (9)	0.0256 (3)
O5	0.48315 (12)	0.38305 (7)	0.72159 (10)	0.0347 (3)
O6	0.41903 (11)	0.28056 (7)	0.79505 (9)	0.0323 (3)
O7	0.14708 (10)	0.33953 (6)	0.79639 (7)	0.0213 (2)
O8	0.24146 (10)	0.43489 (6)	0.90850 (8)	0.0256 (3)
O9	0.18879 (11)	0.31437 (6)	0.95619 (8)	0.0280 (3)
O10	−0.07710 (10)	0.33045 (6)	0.60052 (8)	0.0237 (2)
O11	−0.26269 (11)	0.35436 (7)	0.52419 (10)	0.0334 (3)
O12	−0.17766 (11)	0.25301 (7)	0.46728 (8)	0.0302 (3)
C1	0.11235 (13)	0.34044 (8)	0.63322 (10)	0.0189 (3)
C2	0.08925 (14)	0.39261 (8)	0.55016 (11)	0.0205 (3)
H2B	0.0296	0.4252	0.5457	0.025*
H2C	0.1518	0.4227	0.5563	0.025*
C3	0.21256 (13)	0.29377 (8)	0.64564 (12)	0.0213 (3)
H3B	0.2282	0.2619	0.6995	0.026*
H3C	0.2015	0.2629	0.5915	0.026*
C4	0.12796 (14)	0.38928 (8)	0.71795 (11)	0.0203 (3)
H4A	0.1888	0.4222	0.7284	0.024*
H4B	0.0643	0.4191	0.7090	0.024*
C5	0.01947 (13)	0.28597 (8)	0.61833 (11)	0.0207 (3)
H5B	0.0121	0.2538	0.5660	0.025*
H5C	0.0322	0.2555	0.6730	0.025*
C6	0.17148 (13)	0.40800 (8)	0.37554 (10)	0.0193 (3)
C7	0.20491 (14)	0.48153 (9)	0.38533 (12)	0.0246 (3)
H7A	0.1592	0.5190	0.3905	0.030*
C8	0.30696 (15)	0.49811 (9)	0.38722 (13)	0.0284 (4)
H8B	0.3296	0.5473	0.3936	0.034*
C9	0.37690 (14)	0.44311 (10)	0.37979 (12)	0.0265 (3)
C10	0.34113 (15)	0.36985 (9)	0.36990 (12)	0.0274 (4)
H10A	0.3868	0.3324	0.3647	0.033*
C11	0.23934 (15)	0.35158 (9)	0.36764 (12)	0.0249 (3)
H11B	0.2165	0.3025	0.3610	0.030*
C12	0.48782 (16)	0.46125 (12)	0.38123 (15)	0.0365 (4)
H12B	0.5096	0.5085	0.4104	0.055*
H12C	0.4874	0.4630	0.3189	0.055*
H12D	0.5372	0.4238	0.4154	0.055*
C13	0.44820 (14)	0.25381 (9)	0.64082 (12)	0.0250 (3)
C14	0.48460 (15)	0.27930 (10)	0.57213 (12)	0.0279 (4)
H14A	0.4921	0.3298	0.5641	0.033*
C15	0.50952 (15)	0.22807 (10)	0.51580 (13)	0.0296 (4)
H15A	0.5344	0.2447	0.4699	0.035*
C16	0.49800 (15)	0.15206 (10)	0.52657 (13)	0.0290 (4)
C17	0.46100 (15)	0.12852 (10)	0.59613 (14)	0.0306 (4)
H17A	0.4530	0.0780	0.6042	0.037*
C18	0.43601 (14)	0.17829 (9)	0.65301 (13)	0.0266 (3)
H18A	0.4113	0.1617	0.6990	0.032*
C19	0.52492 (17)	0.09697 (12)	0.46446 (14)	0.0370 (4)
H19A	0.5668	0.0573	0.5013	0.056*
H19B	0.5654	0.1212	0.4320	0.056*
H19C	0.4597	0.0773	0.4205	0.056*
C20	0.04014 (14)	0.41323 (8)	0.88336 (11)	0.0211 (3)
C21	−0.04285 (15)	0.36589 (9)	0.88235 (12)	0.0262 (4)
H21A	−0.0325	0.3148	0.8863	0.031*
C22	−0.14120 (15)	0.39600 (10)	0.87544 (12)	0.0275 (4)
H22A	−0.1969	0.3646	0.8750	0.033*
C23	−0.15853 (15)	0.47227 (10)	0.86912 (12)	0.0257 (3)
C24	−0.07485 (16)	0.51828 (10)	0.86920 (13)	0.0295 (4)
H24A	−0.0855	0.5693	0.8647	0.035*
C25	0.02422 (15)	0.48965 (9)	0.87594 (12)	0.0267 (4)
H25A	0.0795	0.5211	0.8755	0.032*
C26	−0.26526 (16)	0.50341 (11)	0.86390 (14)	0.0345 (4)
H26A	−0.2727	0.5529	0.8395	0.052*
H26B	−0.2694	0.5043	0.9248	0.052*
H26C	−0.3219	0.4729	0.8240	0.052*
C27	−0.21526 (13)	0.23237 (9)	0.61915 (12)	0.0229 (3)
C28	−0.21199 (14)	0.15680 (9)	0.60537 (12)	0.0250 (3)
H28A	−0.1927	0.1383	0.5571	0.030*
C29	−0.23782 (15)	0.10914 (10)	0.66464 (13)	0.0289 (4)
H29A	−0.2360	0.0582	0.6556	0.035*
C30	−0.26628 (15)	0.13558 (11)	0.73704 (13)	0.0294 (4)
C31	−0.26943 (15)	0.21215 (11)	0.74919 (13)	0.0304 (4)
H31A	−0.2891	0.2307	0.7972	0.037*
C32	−0.24395 (15)	0.26053 (10)	0.69117 (12)	0.0278 (4)
H32A	−0.2459	0.3114	0.7000	0.033*
C33	−0.29291 (18)	0.08257 (13)	0.80129 (15)	0.0412 (5)
H33A	−0.3346	0.0421	0.7661	0.062*
H33B	−0.3335	0.1080	0.8328	0.062*
H33C	−0.2276	0.0637	0.8460	0.062*

	U11	U22	U33	U12	U13	U23
S1	0.0232 (2)	0.02041 (17)	0.01541 (17)	0.00089 (14)	0.00691 (15)	−0.00004 (13)
S2	0.0271 (2)	0.0254 (2)	0.0251 (2)	−0.00384 (16)	0.00944 (17)	−0.00123 (16)
S3	0.0284 (2)	0.01908 (17)	0.01522 (18)	0.00331 (14)	0.00744 (16)	0.00123 (13)
S4	0.0255 (2)	0.02166 (18)	0.0239 (2)	0.00318 (15)	0.00649 (17)	−0.00113 (15)
O1	0.0300 (6)	0.0187 (5)	0.0152 (5)	−0.0004 (4)	0.0103 (5)	−0.0008 (4)
O2	0.0259 (6)	0.0246 (5)	0.0243 (6)	0.0052 (5)	0.0090 (5)	0.0024 (5)
O3	0.0298 (7)	0.0288 (6)	0.0193 (6)	−0.0038 (5)	0.0060 (5)	−0.0053 (5)
O4	0.0273 (6)	0.0218 (5)	0.0310 (6)	0.0007 (5)	0.0143 (5)	0.0025 (5)
O5	0.0381 (8)	0.0302 (6)	0.0361 (7)	−0.0115 (5)	0.0133 (6)	−0.0044 (5)
O6	0.0386 (8)	0.0343 (7)	0.0228 (6)	−0.0049 (6)	0.0093 (6)	0.0004 (5)
O7	0.0321 (7)	0.0177 (5)	0.0151 (5)	0.0052 (4)	0.0097 (5)	0.0022 (4)
O8	0.0265 (6)	0.0254 (6)	0.0227 (6)	0.0006 (5)	0.0057 (5)	−0.0001 (5)
O9	0.0401 (8)	0.0243 (6)	0.0180 (6)	0.0057 (5)	0.0085 (5)	0.0053 (4)
O10	0.0224 (6)	0.0204 (5)	0.0289 (6)	0.0013 (4)	0.0099 (5)	−0.0037 (5)
O11	0.0310 (7)	0.0252 (6)	0.0390 (8)	0.0076 (5)	0.0063 (6)	0.0022 (5)
O12	0.0381 (8)	0.0297 (6)	0.0213 (6)	0.0014 (5)	0.0088 (5)	−0.0021 (5)
C1	0.0248 (8)	0.0175 (6)	0.0161 (7)	0.0020 (6)	0.0091 (6)	0.0007 (5)
C2	0.0287 (9)	0.0184 (6)	0.0165 (7)	0.0010 (6)	0.0107 (6)	−0.0016 (5)
C3	0.0241 (8)	0.0197 (7)	0.0225 (8)	0.0012 (6)	0.0110 (7)	−0.0009 (6)
C4	0.0294 (9)	0.0172 (6)	0.0158 (7)	0.0033 (6)	0.0099 (6)	0.0020 (5)
C5	0.0245 (8)	0.0182 (6)	0.0212 (7)	0.0027 (6)	0.0103 (7)	0.0015 (6)
C6	0.0240 (8)	0.0199 (7)	0.0154 (7)	0.0012 (6)	0.0088 (6)	0.0012 (5)
C7	0.0283 (9)	0.0188 (7)	0.0278 (8)	0.0016 (6)	0.0112 (7)	−0.0021 (6)
C8	0.0286 (9)	0.0227 (7)	0.0356 (10)	−0.0018 (6)	0.0133 (8)	−0.0006 (7)
C9	0.0257 (9)	0.0316 (8)	0.0244 (8)	0.0025 (7)	0.0115 (7)	0.0035 (7)
C10	0.0327 (10)	0.0254 (8)	0.0293 (9)	0.0092 (7)	0.0175 (8)	0.0048 (7)
C11	0.0348 (10)	0.0178 (7)	0.0263 (8)	0.0033 (6)	0.0159 (7)	0.0018 (6)
C12	0.0290 (10)	0.0412 (10)	0.0443 (12)	0.0038 (8)	0.0190 (9)	0.0072 (9)
C13	0.0197 (8)	0.0280 (8)	0.0260 (8)	0.0004 (6)	0.0066 (7)	−0.0001 (7)
C14	0.0246 (9)	0.0318 (8)	0.0254 (8)	0.0006 (7)	0.0066 (7)	0.0050 (7)
C15	0.0270 (9)	0.0374 (9)	0.0237 (8)	0.0020 (7)	0.0083 (7)	0.0040 (7)
C16	0.0222 (9)	0.0348 (9)	0.0281 (9)	0.0030 (7)	0.0064 (7)	−0.0026 (7)
C17	0.0265 (9)	0.0282 (8)	0.0381 (10)	0.0001 (7)	0.0125 (8)	−0.0001 (7)
C18	0.0221 (8)	0.0274 (8)	0.0317 (9)	−0.0013 (6)	0.0111 (7)	0.0012 (7)
C19	0.0365 (11)	0.0414 (10)	0.0337 (10)	0.0048 (8)	0.0130 (9)	−0.0035 (8)
C20	0.0285 (9)	0.0197 (7)	0.0169 (7)	0.0023 (6)	0.0105 (6)	0.0002 (6)
C21	0.0354 (10)	0.0204 (7)	0.0254 (8)	−0.0007 (6)	0.0140 (7)	0.0004 (6)
C22	0.0319 (10)	0.0280 (8)	0.0252 (8)	−0.0043 (7)	0.0130 (7)	−0.0007 (7)
C23	0.0311 (9)	0.0290 (8)	0.0191 (8)	0.0028 (7)	0.0116 (7)	−0.0006 (6)
C24	0.0381 (10)	0.0216 (7)	0.0336 (9)	0.0063 (7)	0.0185 (8)	0.0012 (7)
C25	0.0331 (10)	0.0205 (7)	0.0295 (9)	−0.0013 (6)	0.0149 (8)	0.0004 (6)
C26	0.0344 (11)	0.0411 (10)	0.0322 (10)	0.0068 (8)	0.0168 (8)	−0.0009 (8)
C27	0.0178 (8)	0.0248 (7)	0.0242 (8)	0.0014 (6)	0.0051 (6)	−0.0021 (6)
C28	0.0228 (8)	0.0244 (8)	0.0300 (9)	0.0010 (6)	0.0120 (7)	−0.0043 (6)
C29	0.0254 (9)	0.0257 (8)	0.0373 (10)	−0.0005 (6)	0.0133 (8)	−0.0007 (7)
C30	0.0204 (9)	0.0401 (10)	0.0284 (9)	−0.0018 (7)	0.0093 (7)	0.0017 (7)
C31	0.0254 (9)	0.0430 (10)	0.0236 (8)	0.0032 (7)	0.0097 (7)	−0.0056 (7)
C32	0.0272 (9)	0.0296 (8)	0.0238 (8)	0.0034 (7)	0.0056 (7)	−0.0064 (7)
C33	0.0358 (11)	0.0524 (12)	0.0406 (12)	−0.0050 (9)	0.0198 (9)	0.0083 (10)

S1—O3	1.4238 (12)	C12—H12C	0.96
S1—O2	1.4315 (12)	C12—H12D	0.96
S1—O1	1.5833 (11)	C13—C14	1.389 (2)
S1—C6	1.7453 (17)	C13—C18	1.392 (2)
S2—O5	1.4244 (13)	C14—C15	1.386 (3)
S2—O6	1.4314 (13)	C14—H14A	0.93
S2—O4	1.5840 (13)	C15—C16	1.396 (3)
S2—C13	1.7435 (18)	C15—H15A	0.93
S3—O9	1.4252 (12)	C16—C17	1.395 (3)
S3—O8	1.4271 (13)	C16—C19	1.508 (3)
S3—O7	1.5848 (11)	C17—C18	1.375 (3)
S3—C20	1.7518 (17)	C17—H17A	0.93
S4—O11	1.4240 (13)	C18—H18A	0.93
S4—O12	1.4274 (13)	C19—H19A	0.96
S4—O10	1.5899 (13)	C19—H19B	0.96
S4—C27	1.7404 (18)	C19—H19C	0.96
O1—C2	1.4578 (18)	C20—C21	1.391 (2)
O4—C3	1.458 (2)	C20—C25	1.393 (2)
O7—C4	1.4546 (18)	C21—C22	1.385 (3)
O10—C5	1.4559 (19)	C21—H21A	0.93
C1—C4	1.528 (2)	C22—C23	1.393 (2)
C1—C3	1.530 (2)	C22—H22A	0.93
C1—C2	1.531 (2)	C23—C24	1.388 (3)
C1—C5	1.531 (2)	C23—C26	1.502 (3)
C2—H2B	0.97	C24—C25	1.384 (3)
C2—H2C	0.97	C24—H24A	0.93
C3—H3B	0.97	C25—H25A	0.93
C3—H3C	0.97	C26—H26A	0.96
C4—H4A	0.97	C26—H26B	0.96
C4—H4B	0.97	C26—H26C	0.96
C5—H5B	0.97	C27—C28	1.383 (2)
C5—H5C	0.97	C27—C32	1.391 (2)
C6—C7	1.390 (2)	C28—C29	1.383 (2)
C6—C11	1.394 (2)	C28—H28A	0.93
C7—C8	1.380 (2)	C29—C30	1.384 (3)
C7—H7A	0.93	C29—H29A	0.93
C8—C9	1.392 (2)	C30—C31	1.396 (3)
C8—H8B	0.93	C30—C33	1.506 (3)
C9—C10	1.395 (2)	C31—C32	1.375 (3)
C9—C12	1.503 (3)	C31—H31A	0.93
C10—C11	1.382 (3)	C32—H32A	0.93
C10—H10A	0.93	C33—H33A	0.96
C11—H11B	0.93	C33—H33B	0.96
C12—H12B	0.96	C33—H33C	0.96
O3—S1—O2	120.75 (8)	C9—C12—H12C	109.5
O3—S1—O1	103.71 (7)	H12B—C12—H12C	109.5
O2—S1—O1	108.68 (7)	C9—C12—H12D	109.5
O3—S1—C6	109.30 (8)	H12B—C12—H12D	109.5
O2—S1—C6	109.11 (7)	H12C—C12—H12D	109.5
O1—S1—C6	103.91 (7)	C14—C13—C18	121.01 (16)
O5—S2—O6	119.85 (8)	C14—C13—S2	118.89 (13)
O5—S2—O4	103.83 (8)	C18—C13—S2	120.09 (14)
O6—S2—O4	108.03 (8)	C15—C14—C13	118.81 (17)
O5—S2—C13	110.30 (9)	C15—C14—H14A	120.6
O6—S2—C13	108.69 (8)	C13—C14—H14A	120.6
O4—S2—C13	105.06 (8)	C14—C15—C16	121.31 (17)
O9—S3—O8	120.30 (8)	C14—C15—H15A	119.3
O9—S3—O7	103.79 (7)	C16—C15—H15A	119.3
O8—S3—O7	108.60 (7)	C17—C16—C15	118.28 (17)
O9—S3—C20	109.69 (8)	C17—C16—C19	120.99 (17)
O8—S3—C20	109.06 (7)	C15—C16—C19	120.73 (17)
O7—S3—C20	104.11 (7)	C18—C17—C16	121.45 (17)
O11—S4—O12	119.87 (8)	C18—C17—H17A	119.3
O11—S4—O10	103.51 (7)	C16—C17—H17A	119.3
O12—S4—O10	108.71 (7)	C17—C18—C13	119.13 (17)
O11—S4—C27	109.74 (8)	C17—C18—H18A	120.4
O12—S4—C27	109.16 (8)	C13—C18—H18A	120.4
O10—S4—C27	104.68 (7)	C16—C19—H19A	109.5
C2—O1—S1	117.87 (9)	C16—C19—H19B	109.5
C3—O4—S2	118.41 (10)	H19A—C19—H19B	109.5
C4—O7—S3	117.34 (9)	C16—C19—H19C	109.5
C5—O10—S4	117.92 (10)	H19A—C19—H19C	109.5
C4—C1—C3	111.13 (13)	H19B—C19—H19C	109.5
C4—C1—C2	106.71 (12)	C21—C20—C25	120.63 (16)
C3—C1—C2	110.60 (13)	C21—C20—S3	119.40 (12)
C4—C1—C5	110.94 (13)	C25—C20—S3	119.97 (13)
C3—C1—C5	106.66 (12)	C22—C21—C20	118.94 (15)
C2—C1—C5	110.85 (13)	C22—C21—H21A	120.5
O1—C2—C1	106.24 (11)	C20—C21—H21A	120.5
O1—C2—H2B	110.5	C21—C22—C23	121.42 (17)
C1—C2—H2B	110.5	C21—C22—H22A	119.3
O1—C2—H2C	110.5	C23—C22—H22A	119.3
C1—C2—H2C	110.5	C24—C23—C22	118.54 (17)
H2B—C2—H2C	108.7	C24—C23—C26	121.25 (16)
O4—C3—C1	107.03 (12)	C22—C23—C26	120.21 (17)
O4—C3—H3B	110.3	C25—C24—C23	121.23 (16)
C1—C3—H3B	110.3	C25—C24—H24A	119.4
O4—C3—H3C	110.3	C23—C24—H24A	119.4
C1—C3—H3C	110.3	C24—C25—C20	119.23 (17)
H3B—C3—H3C	108.6	C24—C25—H25A	120.4
O7—C4—C1	106.63 (11)	C20—C25—H25A	120.4
O7—C4—H4A	110.4	C23—C26—H26A	109.5
C1—C4—H4A	110.4	C23—C26—H26B	109.5
O7—C4—H4B	110.4	H26A—C26—H26B	109.5
C1—C4—H4B	110.4	C23—C26—H26C	109.5
H4A—C4—H4B	108.6	H26A—C26—H26C	109.5
O10—C5—C1	106.62 (12)	H26B—C26—H26C	109.5
O10—C5—H5B	110.4	C28—C27—C32	120.99 (16)
C1—C5—H5B	110.4	C28—C27—S4	119.91 (13)
O10—C5—H5C	110.4	C32—C27—S4	119.03 (13)
C1—C5—H5C	110.4	C27—C28—C29	118.85 (16)
H5B—C5—H5C	108.6	C27—C28—H28A	120.6
C7—C6—C11	120.93 (16)	C29—C28—H28A	120.6
C7—C6—S1	120.88 (13)	C28—C29—C30	121.41 (16)
C11—C6—S1	118.18 (12)	C28—C29—H29A	119.3
C8—C7—C6	118.92 (15)	C30—C29—H29A	119.3
C8—C7—H7A	120.5	C29—C30—C31	118.61 (17)
C6—C7—H7A	120.5	C29—C30—C33	120.43 (18)
C7—C8—C9	121.64 (16)	C31—C30—C33	120.96 (18)
C7—C8—H8B	119.2	C32—C31—C30	120.96 (17)
C9—C8—H8B	119.2	C32—C31—H31A	119.5
C8—C9—C10	118.19 (16)	C30—C31—H31A	119.5
C8—C9—C12	121.62 (17)	C31—C32—C27	119.18 (16)
C10—C9—C12	120.19 (16)	C31—C32—H32A	120.4
C11—C10—C9	121.47 (16)	C27—C32—H32A	120.4
C11—C10—H10A	119.3	C30—C33—H33A	109.5
C9—C10—H10A	119.3	C30—C33—H33B	109.5
C10—C11—C6	118.85 (15)	H33A—C33—H33B	109.5
C10—C11—H11B	120.6	C30—C33—H33C	109.5
C6—C11—H11B	120.6	H33A—C33—H33C	109.5
C9—C12—H12B	109.5	H33B—C33—H33C	109.5
O3—S1—O1—C2	−170.85 (11)	O4—S2—C13—C14	83.71 (15)
O2—S1—O1—C2	−41.20 (13)	O5—S2—C13—C18	151.46 (14)
C6—S1—O1—C2	74.89 (12)	O6—S2—C13—C18	18.19 (17)
O5—S2—O4—C3	−173.46 (11)	O4—S2—C13—C18	−97.23 (15)
O6—S2—O4—C3	−45.20 (13)	C18—C13—C14—C15	−0.4 (3)
C13—S2—O4—C3	70.68 (13)	S2—C13—C14—C15	178.62 (14)
O9—S3—O7—C4	−176.31 (12)	C13—C14—C15—C16	0.4 (3)
O8—S3—O7—C4	−47.20 (13)	C14—C15—C16—C17	−0.3 (3)
C20—S3—O7—C4	68.89 (13)	C14—C15—C16—C19	179.71 (18)
O11—S4—O10—C5	−170.33 (11)	C15—C16—C17—C18	0.1 (3)
O12—S4—O10—C5	−41.85 (13)	C19—C16—C17—C18	−179.86 (18)
C27—S4—O10—C5	74.70 (12)	C16—C17—C18—C13	−0.1 (3)
S1—O1—C2—C1	−175.72 (10)	C14—C13—C18—C17	0.3 (3)
C4—C1—C2—O1	−173.83 (13)	S2—C13—C18—C17	−178.76 (14)
C3—C1—C2—O1	65.17 (16)	O9—S3—C20—C21	−37.17 (15)
C5—C1—C2—O1	−52.92 (16)	O8—S3—C20—C21	−170.84 (13)
S2—O4—C3—C1	154.00 (10)	O7—S3—C20—C21	73.38 (14)
C4—C1—C3—O4	−60.20 (16)	O9—S3—C20—C25	142.69 (14)
C2—C1—C3—O4	58.14 (16)	O8—S3—C20—C25	9.02 (16)
C5—C1—C3—O4	178.76 (12)	O7—S3—C20—C25	−106.76 (14)
S3—O7—C4—C1	−179.78 (10)	C25—C20—C21—C22	−1.1 (3)
C3—C1—C4—O7	−60.81 (16)	S3—C20—C21—C22	178.76 (13)
C2—C1—C4—O7	178.53 (13)	C20—C21—C22—C23	0.3 (3)
C5—C1—C4—O7	57.68 (16)	C21—C22—C23—C24	0.5 (3)
S4—O10—C5—C1	154.75 (10)	C21—C22—C23—C26	−178.59 (17)
C4—C1—C5—O10	62.45 (15)	C22—C23—C24—C25	−0.4 (3)
C3—C1—C5—O10	−176.39 (12)	C26—C23—C24—C25	178.66 (16)
C2—C1—C5—O10	−55.93 (15)	C23—C24—C25—C20	−0.4 (3)
O3—S1—C6—C7	142.11 (13)	C21—C20—C25—C24	1.2 (3)
O2—S1—C6—C7	8.11 (16)	S3—C20—C25—C24	−178.69 (13)
O1—S1—C6—C7	−107.68 (14)	O11—S4—C27—C28	138.81 (14)
O3—S1—C6—C11	−37.20 (15)	O12—S4—C27—C28	5.58 (17)
O2—S1—C6—C11	−171.20 (12)	O10—S4—C27—C28	−110.67 (14)
O1—S1—C6—C11	73.01 (14)	O11—S4—C27—C32	−38.17 (16)
C11—C6—C7—C8	−0.1 (2)	O12—S4—C27—C32	−171.40 (14)
S1—C6—C7—C8	−179.35 (13)	O10—S4—C27—C32	72.35 (15)
C6—C7—C8—C9	−0.1 (3)	C32—C27—C28—C29	0.0 (3)
C7—C8—C9—C10	0.2 (3)	S4—C27—C28—C29	−176.92 (14)
C7—C8—C9—C12	179.59 (17)	C27—C28—C29—C30	−0.2 (3)
C8—C9—C10—C11	−0.1 (3)	C28—C29—C30—C31	0.5 (3)
C12—C9—C10—C11	−179.50 (17)	C28—C29—C30—C33	−179.33 (18)
C9—C10—C11—C6	0.0 (3)	C29—C30—C31—C32	−0.6 (3)
C7—C6—C11—C10	0.2 (2)	C33—C30—C31—C32	179.26 (18)
S1—C6—C11—C10	179.46 (13)	C30—C31—C32—C27	0.4 (3)
O5—S2—C13—C14	−27.60 (17)	C28—C27—C32—C31	−0.1 (3)
O6—S2—C13—C14	−160.86 (14)	S4—C27—C32—C31	176.88 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···O4	0.97	2.48	2.849 (2)	102
C3—H3B···O6	0.97	2.47	2.905 (2)	107
C3—H3B···O7	0.97	2.55	2.876 (2)	100
C3—H3C···O9i	0.97	2.46	3.433 (2)	175
C4—H4A···O4	0.97	2.55	2.879 (2)	100
C5—H5B···O12	0.97	2.44	2.888 (2)	107
C5—H5C···O7	0.97	2.49	2.8396 (19)	101
C7—H7A···O2	0.93	2.58	2.937 (2)	103
C8—H8B···O11ii	0.93	2.52	3.140 (2)	124
C10—H10A···O6i	0.93	2.41	3.257 (2)	151
C18—H18A···O6	0.93	2.59	2.932 (2)	103
C22—H22A···O12iii	0.93	2.52	3.154 (2)	126
C25—H25A···O8	0.93	2.56	2.924 (2)	104
C28—H28A···O12	0.93	2.54	2.905 (2)	104
C29—H29A···O8iv	0.93	2.42	3.334 (2)	165
C31—H31A···O12iii	0.93	2.53	3.209 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2C⋯O4	0.97	2.48	2.849 (2)	102
C3—H3B⋯O6	0.97	2.47	2.905 (2)	107
C3—H3B⋯O7	0.97	2.55	2.876 (2)	100
C3—H3C⋯O9i	0.97	2.46	3.433 (2)	175
C4—H4A⋯O4	0.97	2.55	2.879 (2)	100
C5—H5B⋯O12	0.97	2.44	2.888 (2)	107
C5—H5C⋯O7	0.97	2.49	2.8396 (19)	101
C7—H7A⋯O2	0.93	2.58	2.937 (2)	103
C8—H8B⋯O11ii	0.93	2.52	3.140 (2)	124
C10—H10A⋯O6i	0.93	2.41	3.257 (2)	151
C18—H18A⋯O6	0.93	2.59	2.932 (2)	103
C22—H22A⋯O12iii	0.93	2.52	3.154 (2)	126
C25—H25A⋯O8	0.93	2.56	2.924 (2)	104
C28—H28A⋯O12	0.93	2.54	2.905 (2)	104
C29—H29A⋯O8iv	0.93	2.42	3.334 (2)	165
C31—H31A⋯O12iii	0.93	2.53	3.209 (2)	130

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .