2,3:4,5-Di-O-isopropyl-idenefructos-1-yl p-toluene-sulfonate.

The title compound, C(19)H(26)O(8)S, has been synthesized from 2,3:4,5-di-O-isopropyl-idene-β-d-fructopyran-ose. The absolute configuration of the fused ring is confirmed by anomalous dispersion effects in the diffraction measurement. The six-membered β-fructopyran-ose ring has a twist-boat conformation with the two five-membered rings trans to each other. In the crystal, inter-molecular non-classical C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For details of the synthesis of the title compound and its analogues, see: Hirst et al. (1953 ▶); Reitz et al. (1989 ▶); Dekany et al. (2007 ▶). For a related structure, see: Lis & Weichsel (1987 ▶).

Experimental

Crystal data

C19H26O8S

M = 414.47

Monoclinic,

a = 13.870 (5) Å

b = 10.153 (4) Å

c = 15.715 (6) Å

β = 106.831 (4)°

V = 2118.2 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 273 K

0.43 × 0.36 × 0.27 mm

Data collection

Bruker SMART APEX CCD diffractometer

10503 measured reflections

6948 independent reflections

6040 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.04

6948 reflections

506 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 3010 Friedel pairs

Flack parameter: −0.02 (5)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536810044582/rk2243sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044582/rk2243Isup2.hkl

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

C19H26O8S	F(000) = 880
Mr = 414.47	Dx = 1.300 Mg m−3
Monoclinic, P21	Melting point: 357 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 13.870 (5) Å	Cell parameters from 4356 reflections
b = 10.153 (4) Å	θ = 2.4–23.0°
c = 15.715 (6) Å	µ = 0.19 mm−1
β = 106.831 (4)°	T = 273 K
V = 2118.2 (14) Å3	Block, colourless
Z = 4	0.43 × 0.36 × 0.27 mm

Bruker SMART APEX CCD diffractometer	6040 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
graphite	θmax = 25.0°, θmin = 2.3°
φ– and ω–scans	h = −16→9
10503 measured reflections	k = −12→12
6948 independent reflections	l = −18→18

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.015P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.15 e Å−3
6948 reflections	Δρmin = −0.19 e Å−3
506 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
13 restraints	Extinction coefficient: 0.0092 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 3010 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.02 (5)

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
S1	0.24587 (4)	0.18747 (6)	0.02021 (4)	0.05469 (18)
O3	0.19989 (12)	−0.26856 (17)	0.18097 (10)	0.0516 (4)
O2	0.15726 (12)	−0.22131 (18)	0.03390 (10)	0.0503 (4)
O6	0.22579 (12)	0.04415 (17)	0.05015 (11)	0.0543 (4)
O5	0.50852 (14)	−0.3218 (2)	0.16864 (15)	0.0765 (6)
C1	0.25987 (17)	−0.1891 (2)	0.06751 (16)	0.0449 (5)
O4	0.45357 (13)	−0.1488 (2)	0.23044 (13)	0.0684 (5)
C2	0.27894 (17)	−0.1881 (3)	0.16876 (15)	0.0469 (6)
H2A	0.2720	−0.0982	0.1890	0.056*
C13	0.36794 (17)	0.2246 (2)	0.08676 (16)	0.0469 (6)
C12	0.2830 (2)	−0.0621 (3)	0.02666 (18)	0.0558 (7)
H12A	0.3545	−0.0430	0.0485	0.067*
H12B	0.2652	−0.0710	−0.0375	0.067*
C14	0.4482 (2)	0.2255 (3)	0.05212 (18)	0.0602 (7)
H14A	0.4393	0.2034	−0.0071	0.072*
C3	0.37782 (19)	−0.2460 (3)	0.22273 (17)	0.0554 (6)
H3A	0.3737	−0.2705	0.2819	0.066*
C8	0.0499 (2)	−0.1399 (3)	0.11720 (18)	0.0591 (7)
H8A	0.0892	−0.0606	0.1290	0.089*
H8B	0.0236	−0.1581	0.1662	0.089*
H8C	−0.0049	−0.1289	0.0639	0.089*
O8	0.17471 (14)	0.26665 (19)	0.04647 (15)	0.0734 (6)
O7	0.24594 (14)	0.1835 (2)	−0.06986 (12)	0.0739 (5)
C6	0.11497 (18)	−0.2526 (3)	0.10546 (15)	0.0482 (6)
C4	0.4142 (2)	−0.3638 (3)	0.1795 (2)	0.0619 (7)
H4A	0.4240	−0.4408	0.2186	0.074*
C18	0.3815 (2)	0.2560 (3)	0.17503 (18)	0.0604 (7)
H18A	0.3272	0.2549	0.1985	0.073*
C16	0.5571 (2)	0.2930 (3)	0.1936 (2)	0.0713 (8)
C17	0.4754 (2)	0.2886 (3)	0.2274 (2)	0.0702 (8)
H17A	0.4847	0.3083	0.2870	0.084*
C11	0.6036 (3)	−0.1244 (4)	0.1876 (3)	0.0982 (12)
H11A	0.5631	−0.0963	0.1300	0.147*
H11B	0.6621	−0.1697	0.1818	0.147*
H11C	0.6241	−0.0491	0.2254	0.147*
C7	0.0593 (2)	−0.3813 (3)	0.0869 (2)	0.0660 (7)
H7B	0.1044	−0.4494	0.0799	0.099*
H7C	0.0045	−0.3739	0.0334	0.099*
H7D	0.0335	−0.4029	0.1356	0.099*
C15	0.5421 (2)	0.2597 (3)	0.1066 (2)	0.0726 (8)
H15A	0.5967	0.2601	0.0834	0.087*
C9	0.5432 (2)	−0.2156 (3)	0.2276 (2)	0.0689 (8)
C10	0.6013 (3)	−0.2650 (5)	0.3194 (2)	0.1077 (14)
H10A	0.5595	−0.3235	0.3411	0.162*
H10B	0.6208	−0.1915	0.3591	0.162*
H10C	0.6605	−0.3111	0.3158	0.162*
C19	0.6594 (3)	0.3360 (5)	0.2510 (3)	0.1266 (17)
H19A	0.7068	0.3326	0.2170	0.190*
H19B	0.6812	0.2782	0.3013	0.190*
H19C	0.6553	0.4245	0.2712	0.190*
S2	0.20695 (5)	0.40282 (6)	0.37302 (5)	0.05712 (18)
O11	0.02664 (12)	0.86733 (17)	0.33953 (11)	0.0502 (4)
O10	0.03125 (11)	0.70729 (17)	0.44201 (10)	0.0522 (4)
O13	0.29576 (12)	0.88143 (16)	0.38639 (11)	0.0529 (4)
C22	0.19864 (19)	0.9338 (2)	0.37952 (16)	0.0453 (6)
H22A	0.1779	0.9944	0.3289	0.054*
O9	0.17593 (13)	0.80561 (16)	0.53013 (10)	0.0518 (4)
O14	0.15205 (17)	0.53361 (18)	0.38479 (14)	0.0729 (6)
O16	0.24890 (14)	0.34602 (18)	0.45814 (13)	0.0661 (5)
C32	0.1013 (2)	0.3142 (2)	0.31216 (17)	0.0509 (6)
C24	0.1586 (2)	0.9447 (2)	0.52606 (17)	0.0549 (6)
H24A	0.1823	0.9818	0.5854	0.066*
H24B	0.0870	0.9619	0.5032	0.066*
O12	0.31802 (15)	1.0050 (2)	0.50883 (13)	0.0710 (6)
C28	0.3671 (2)	0.9641 (3)	0.4459 (2)	0.0602 (7)
C31	0.1972 (2)	0.6168 (2)	0.46030 (17)	0.0509 (6)
H31A	0.2656	0.6396	0.4617	0.061*
H31B	0.1991	0.5717	0.5151	0.061*
C25	−0.03423 (18)	0.7689 (3)	0.36376 (16)	0.0541 (6)
C21	0.12717 (17)	0.8185 (2)	0.36592 (15)	0.0407 (5)
H21A	0.1378	0.7603	0.3197	0.049*
C20	0.13331 (17)	0.7389 (2)	0.45007 (15)	0.0428 (5)
C34	−0.0497 (2)	0.1991 (3)	0.30565 (18)	0.0626 (7)
H34A	−0.0964	0.1699	0.3335	0.075*
C23	0.2126 (2)	1.0091 (2)	0.46710 (18)	0.0552 (7)
H23A	0.1900	1.1005	0.4549	0.066*
C35	−0.0641 (2)	0.1689 (3)	0.21767 (18)	0.0613 (7)
C27	−0.0711 (2)	0.6678 (4)	0.29181 (19)	0.0744 (8)
H27A	−0.0145	0.6272	0.2788	0.112*
H27B	−0.1128	0.7098	0.2393	0.112*
H27C	−0.1095	0.6020	0.3115	0.112*
C36	0.0060 (2)	0.2146 (3)	0.17747 (19)	0.0702 (8)
H36A	−0.0027	0.1955	0.1178	0.084*
C26	−0.1181 (2)	0.8387 (4)	0.3889 (2)	0.0783 (9)
H26A	−0.0899	0.9020	0.4348	0.117*
H26B	−0.1571	0.7756	0.4103	0.117*
H26C	−0.1606	0.8830	0.3378	0.117*
C30	0.3934 (3)	1.0791 (3)	0.3967 (3)	0.0906 (11)
H30A	0.3334	1.1276	0.3680	0.136*
H30B	0.4237	1.0477	0.3529	0.136*
H30C	0.4399	1.1355	0.4379	0.136*
C37	0.0877 (2)	0.2872 (3)	0.22333 (18)	0.0644 (7)
H37A	0.1336	0.3180	0.1950	0.077*
C33	0.0311 (2)	0.2706 (3)	0.35331 (18)	0.0583 (7)
H33A	0.0391	0.2901	0.4128	0.070*
C29	0.4569 (2)	0.8816 (4)	0.4933 (3)	0.0996 (12)
H29A	0.4352	0.8091	0.5225	0.149*
H29B	0.5039	0.9346	0.5366	0.149*
H29C	0.4888	0.8484	0.4510	0.149*
O15	0.27212 (17)	0.4276 (3)	0.31983 (16)	0.0931 (7)
C38	−0.1524 (2)	0.0859 (3)	0.1661 (2)	0.0852 (10)
H38A	−0.1498	0.0752	0.1061	0.128*
H38B	−0.2142	0.1288	0.1657	0.128*
H38C	−0.1493	0.0010	0.1938	0.128*
O1	0.31903 (13)	−0.28041 (18)	0.03724 (11)	0.0568 (5)
C5	0.3453 (2)	−0.3965 (3)	0.09017 (19)	0.0605 (7)
H5A	0.3779	−0.4587	0.0607	0.073*
H5B	0.2847	−0.4376	0.0968	0.073*

	U11	U22	U33	U12	U13	U23
S1	0.0471 (3)	0.0582 (4)	0.0548 (4)	−0.0019 (3)	0.0085 (3)	0.0117 (3)
O3	0.0432 (9)	0.0706 (11)	0.0399 (9)	0.0006 (8)	0.0103 (7)	0.0064 (8)
O2	0.0449 (9)	0.0692 (11)	0.0350 (8)	−0.0111 (8)	0.0090 (7)	0.0003 (8)
O6	0.0482 (10)	0.0558 (10)	0.0632 (11)	−0.0051 (8)	0.0230 (9)	0.0019 (9)
O5	0.0488 (10)	0.0854 (13)	0.0957 (14)	0.0052 (11)	0.0212 (10)	−0.0239 (13)
C1	0.0411 (13)	0.0530 (13)	0.0404 (13)	−0.0054 (11)	0.0116 (11)	−0.0050 (11)
O4	0.0443 (10)	0.0787 (12)	0.0768 (13)	−0.0029 (10)	0.0092 (9)	−0.0219 (11)
C2	0.0422 (13)	0.0572 (14)	0.0406 (13)	−0.0010 (11)	0.0110 (11)	−0.0050 (11)
C13	0.0473 (13)	0.0458 (12)	0.0473 (14)	−0.0002 (11)	0.0134 (11)	0.0086 (11)
C12	0.0537 (15)	0.0609 (16)	0.0583 (16)	−0.0078 (13)	0.0250 (13)	−0.0027 (13)
C14	0.0586 (16)	0.0715 (17)	0.0536 (15)	−0.0091 (14)	0.0213 (13)	−0.0044 (13)
C3	0.0441 (14)	0.0722 (17)	0.0483 (14)	0.0015 (13)	0.0110 (12)	−0.0030 (13)
C8	0.0523 (15)	0.0699 (17)	0.0530 (16)	0.0053 (13)	0.0119 (13)	0.0028 (13)
O8	0.0530 (11)	0.0685 (12)	0.0960 (15)	0.0122 (10)	0.0171 (11)	0.0076 (11)
O7	0.0712 (12)	0.0898 (14)	0.0535 (11)	−0.0101 (12)	0.0065 (9)	0.0123 (11)
C6	0.0455 (13)	0.0599 (14)	0.0380 (13)	−0.0044 (11)	0.0101 (11)	0.0040 (11)
C4	0.0549 (16)	0.0600 (16)	0.0679 (19)	0.0063 (13)	0.0130 (14)	0.0035 (14)
C18	0.0576 (16)	0.0723 (18)	0.0554 (16)	0.0026 (14)	0.0227 (14)	0.0001 (14)
C16	0.0549 (17)	0.0755 (19)	0.076 (2)	−0.0036 (15)	0.0064 (15)	−0.0147 (17)
C17	0.0691 (19)	0.083 (2)	0.0536 (17)	0.0049 (17)	0.0095 (15)	−0.0107 (16)
C11	0.067 (2)	0.118 (3)	0.112 (3)	−0.018 (2)	0.030 (2)	−0.021 (2)
C7	0.0628 (17)	0.0686 (16)	0.0664 (18)	−0.0136 (14)	0.0186 (15)	0.0019 (15)
C15	0.0513 (16)	0.089 (2)	0.082 (2)	−0.0105 (15)	0.0273 (16)	−0.0107 (18)
C9	0.0438 (15)	0.088 (2)	0.071 (2)	0.0067 (15)	0.0112 (14)	−0.0128 (17)
C10	0.0609 (19)	0.164 (4)	0.086 (3)	0.014 (2)	0.0016 (18)	0.005 (3)
C19	0.060 (2)	0.160 (4)	0.139 (4)	−0.012 (3)	−0.004 (2)	−0.052 (3)
S2	0.0620 (4)	0.0451 (3)	0.0663 (4)	0.0042 (3)	0.0219 (3)	−0.0012 (3)
O11	0.0450 (9)	0.0576 (10)	0.0464 (10)	0.0058 (8)	0.0108 (8)	0.0128 (8)
O10	0.0472 (9)	0.0647 (11)	0.0468 (9)	−0.0001 (8)	0.0168 (8)	0.0141 (8)
O13	0.0489 (10)	0.0476 (9)	0.0644 (11)	−0.0047 (8)	0.0197 (9)	−0.0083 (8)
C22	0.0530 (15)	0.0384 (13)	0.0446 (14)	0.0023 (11)	0.0144 (12)	0.0041 (10)
O9	0.0688 (11)	0.0470 (9)	0.0364 (9)	0.0030 (8)	0.0099 (8)	−0.0003 (7)
O14	0.0850 (14)	0.0445 (10)	0.0727 (13)	0.0137 (10)	−0.0032 (11)	−0.0102 (9)
O16	0.0684 (9)	0.0575 (8)	0.0679 (9)	0.0060 (7)	0.0124 (7)	0.0032 (7)
C32	0.0615 (16)	0.0379 (12)	0.0535 (16)	0.0074 (11)	0.0168 (13)	−0.0010 (11)
C24	0.0666 (17)	0.0492 (14)	0.0492 (15)	0.0100 (13)	0.0173 (13)	−0.0109 (12)
O12	0.0608 (12)	0.0828 (13)	0.0628 (13)	−0.0097 (11)	0.0076 (10)	−0.0204 (11)
C28	0.0566 (17)	0.0554 (15)	0.0662 (18)	−0.0076 (13)	0.0143 (15)	−0.0122 (14)
C31	0.0577 (15)	0.0418 (12)	0.0502 (15)	0.0016 (11)	0.0110 (13)	0.0013 (11)
C25	0.0476 (14)	0.0702 (17)	0.0444 (14)	−0.0033 (13)	0.0134 (12)	0.0087 (13)
C21	0.0453 (13)	0.0428 (12)	0.0353 (13)	0.0031 (10)	0.0138 (11)	0.0004 (10)
C20	0.0506 (13)	0.0408 (11)	0.0386 (13)	0.0001 (10)	0.0154 (11)	0.0017 (10)
C34	0.0614 (16)	0.0693 (17)	0.0581 (17)	−0.0007 (15)	0.0191 (14)	0.0040 (15)
C23	0.0682 (18)	0.0345 (12)	0.0623 (18)	0.0064 (12)	0.0182 (15)	−0.0082 (12)
C35	0.0672 (17)	0.0543 (14)	0.0536 (17)	0.0073 (14)	0.0038 (14)	0.0042 (14)
C27	0.0708 (18)	0.095 (2)	0.0569 (17)	−0.0270 (18)	0.0178 (14)	−0.0003 (17)
C36	0.090 (2)	0.0724 (19)	0.0467 (16)	0.0062 (17)	0.0179 (15)	−0.0027 (14)
C26	0.0535 (17)	0.115 (3)	0.0705 (19)	0.0194 (17)	0.0243 (15)	0.0182 (18)
C30	0.093 (3)	0.069 (2)	0.115 (3)	−0.0268 (19)	0.040 (2)	−0.009 (2)
C37	0.083 (2)	0.0616 (16)	0.0538 (17)	0.0050 (16)	0.0291 (16)	0.0006 (14)
C33	0.0658 (17)	0.0652 (17)	0.0467 (14)	0.0042 (14)	0.0208 (14)	−0.0026 (13)
C29	0.060 (2)	0.118 (3)	0.109 (3)	0.014 (2)	0.0061 (19)	0.005 (2)
O15	0.0874 (16)	0.1010 (17)	0.1040 (17)	−0.0210 (14)	0.0486 (14)	−0.0096 (14)
C38	0.076 (2)	0.081 (2)	0.081 (2)	−0.0033 (18)	−0.0042 (18)	−0.0040 (18)
O1	0.0623 (11)	0.0611 (11)	0.0511 (10)	0.0026 (9)	0.0232 (9)	−0.0106 (9)
C5	0.0624 (18)	0.0503 (15)	0.0724 (19)	0.0027 (13)	0.0254 (16)	−0.0076 (14)

S1—O7	1.416 (2)	S2—C32	1.749 (3)
S1—O8	1.424 (2)	O11—C21	1.424 (3)
S1—O6	1.5786 (19)	O11—C25	1.429 (3)
S1—C13	1.754 (3)	O10—C20	1.421 (3)
O3—C6	1.419 (3)	O10—C25	1.443 (3)
O3—C2	1.424 (3)	O13—C28	1.422 (3)
O2—C1	1.406 (3)	O13—C22	1.423 (3)
O2—C6	1.446 (3)	C22—C21	1.509 (3)
O6—C12	1.449 (3)	C22—C23	1.537 (4)
O5—C9	1.413 (4)	C22—H22A	0.9800
O5—C4	1.432 (3)	O9—C20	1.400 (3)
C1—O1	1.409 (3)	O9—C24	1.431 (3)
C1—C12	1.516 (4)	O14—C31	1.444 (3)
C1—C2	1.536 (3)	C32—C37	1.381 (4)
O4—C3	1.420 (3)	C32—C33	1.388 (3)
O4—C9	1.428 (3)	C24—C23	1.499 (4)
C2—C3	1.508 (3)	C24—H24A	0.9700
C2—H2A	0.9800	C24—H24B	0.9700
C13—C14	1.373 (3)	O12—C23	1.420 (3)
C13—C18	1.382 (4)	O12—C28	1.416 (3)
C12—H12A	0.9700	C28—C30	1.502 (4)
C12—H12B	0.9700	C28—C29	1.508 (4)
C14—C15	1.381 (4)	C31—C20	1.505 (3)
C14—H14A	0.9300	C31—H31A	0.9700
C3—C4	1.532 (4)	C31—H31B	0.9700
C3—H3A	0.9800	C25—C27	1.503 (4)
C8—C6	1.502 (4)	C25—C26	1.510 (4)
C8—H8A	0.9600	C21—C20	1.531 (3)
C8—H8B	0.9600	C21—H21A	0.9800
C8—H8C	0.9600	C34—C33	1.363 (4)
C6—C7	1.503 (4)	C34—C35	1.373 (4)
C4—C5	1.490 (4)	C34—H34A	0.9300
C4—H4A	0.9800	C23—H23A	0.9800
C18—C17	1.364 (4)	C35—C36	1.384 (4)
C18—H18A	0.9300	C35—C38	1.514 (4)
C16—C15	1.365 (4)	C27—H27A	0.9600
C16—C17	1.384 (4)	C27—H27B	0.9600
C16—C19	1.509 (4)	C27—H27C	0.9600
C17—H17A	0.9300	C36—C37	1.370 (4)
C11—C9	1.502 (5)	C36—H36A	0.9300
C11—H11A	0.9600	C26—H26A	0.9600
C11—H11B	0.9600	C26—H26B	0.9600
C11—H11C	0.9600	C26—H26C	0.9600
C7—H7B	0.9600	C30—H30A	0.9600
C7—H7C	0.9600	C30—H30B	0.9600
C7—H7D	0.9600	C30—H30C	0.9600
C15—H15A	0.9300	C37—H37A	0.9300
C9—C10	1.519 (5)	C33—H33A	0.9300
C10—H10A	0.9600	C29—H29A	0.9600
C10—H10B	0.9600	C29—H29B	0.9600
C10—H10C	0.9600	C29—H29C	0.9600
C19—H19A	0.9600	C38—H38A	0.9600
C19—H19B	0.9600	C38—H38B	0.9600
C19—H19C	0.9600	C38—H38C	0.9600
S2—O16	1.418 (2)	O1—C5	1.428 (3)
S2—O15	1.420 (2)	C5—H5A	0.9700
S2—O14	1.568 (2)	C5—H5B	0.9700
O7—S1—O8	120.45 (13)	C20—O10—C25	110.05 (16)
O7—S1—O6	108.85 (12)	C28—O13—C22	106.98 (18)
O8—S1—O6	103.72 (11)	O13—C22—C21	106.82 (17)
O7—S1—C13	108.79 (12)	O13—C22—C23	104.3 (2)
O8—S1—C13	109.66 (12)	C21—C22—C23	114.8 (2)
O6—S1—C13	104.10 (10)	O13—C22—H22A	110.2
C6—O3—C2	107.86 (17)	C21—C22—H22A	110.2
C1—O2—C6	110.70 (17)	C23—C22—H22A	110.2
C12—O6—S1	116.95 (14)	C20—O9—C24	114.55 (18)
C9—O5—C4	107.4 (2)	C31—O14—S2	118.85 (17)
O2—C1—O1	110.23 (19)	C37—C32—C33	120.0 (3)
O2—C1—C12	110.8 (2)	C37—C32—S2	120.1 (2)
O1—C1—C12	101.59 (17)	C33—C32—S2	119.9 (2)
O2—C1—C2	104.05 (17)	O9—C24—C23	110.54 (19)
O1—C1—C2	114.3 (2)	O9—C24—H24A	109.5
C12—C1—C2	116.0 (2)	C23—C24—H24A	109.5
C3—O4—C9	107.3 (2)	O9—C24—H24B	109.5
O3—C2—C3	108.1 (2)	C23—C24—H24B	109.5
O3—C2—C1	103.14 (18)	H24A—C24—H24B	108.1
C3—C2—C1	115.84 (19)	C23—O12—C28	109.0 (2)
O3—C2—H2A	109.8	O12—C28—O13	104.4 (2)
C3—C2—H2A	109.8	O12—C28—C30	111.6 (2)
C1—C2—H2A	109.8	O13—C28—C30	110.3 (3)
C14—C13—C18	120.4 (2)	O12—C28—C29	108.3 (3)
C14—C13—S1	121.2 (2)	O13—C28—C29	108.4 (2)
C18—C13—S1	118.40 (19)	C30—C28—C29	113.4 (3)
O6—C12—C1	109.05 (18)	O14—C31—C20	106.99 (19)
O6—C12—H12A	109.9	O14—C31—H31A	110.3
C1—C12—H12A	109.9	C20—C31—H31A	110.3
O6—C12—H12B	109.9	O14—C31—H31B	110.3
C1—C12—H12B	109.9	C20—C31—H31B	110.3
H12A—C12—H12B	108.3	H31A—C31—H31B	108.6
C13—C14—C15	118.9 (3)	O11—C25—O10	104.82 (18)
C13—C14—H14A	120.5	O11—C25—C27	112.1 (2)
C15—C14—H14A	120.5	O10—C25—C27	109.8 (2)
O4—C3—C2	107.9 (2)	O11—C25—C26	107.5 (2)
O4—C3—C4	104.43 (19)	O10—C25—C26	108.8 (2)
C2—C3—C4	114.7 (2)	C27—C25—C26	113.4 (2)
O4—C3—H3A	109.9	O11—C21—C22	108.62 (18)
C2—C3—H3A	109.9	O11—C21—C20	103.90 (17)
C4—C3—H3A	109.9	C22—C21—C20	114.7 (2)
C6—C8—H8A	109.5	O11—C21—H21A	109.8
C6—C8—H8B	109.5	C22—C21—H21A	109.8
H8A—C8—H8B	109.5	C20—C21—H21A	109.8
C6—C8—H8C	109.5	O9—C20—O10	109.87 (17)
H8A—C8—H8C	109.5	O9—C20—C31	102.71 (18)
H8B—C8—H8C	109.5	O10—C20—C31	111.34 (19)
O3—C6—O2	104.48 (17)	O9—C20—C21	115.11 (19)
O3—C6—C8	111.6 (2)	O10—C20—C21	103.74 (18)
O2—C6—C8	108.8 (2)	C31—C20—C21	114.26 (18)
O3—C6—C7	108.6 (2)	C33—C34—C35	121.9 (3)
O2—C6—C7	110.0 (2)	C33—C34—H34A	119.0
C8—C6—C7	113.1 (2)	C35—C34—H34A	119.0
O5—C4—C5	108.3 (2)	O12—C23—C24	109.5 (2)
O5—C4—C3	104.5 (2)	O12—C23—C22	104.2 (2)
C5—C4—C3	112.8 (2)	C24—C23—C22	112.4 (2)
O5—C4—H4A	110.3	O12—C23—H23A	110.2
C5—C4—H4A	110.3	C24—C23—H23A	110.2
C3—C4—H4A	110.3	C22—C23—H23A	110.2
C17—C18—C13	119.3 (2)	C34—C35—C36	117.9 (3)
C17—C18—H18A	120.3	C34—C35—C38	121.5 (3)
C13—C18—H18A	120.3	C36—C35—C38	120.6 (3)
C15—C16—C17	118.2 (3)	C25—C27—H27A	109.5
C15—C16—C19	121.0 (3)	C25—C27—H27B	109.5
C17—C16—C19	120.8 (3)	H27A—C27—H27B	109.5
C18—C17—C16	121.4 (3)	C25—C27—H27C	109.5
C18—C17—H17A	119.3	H27A—C27—H27C	109.5
C16—C17—H17A	119.3	H27B—C27—H27C	109.5
C9—C11—H11A	109.5	C37—C36—C35	121.6 (3)
C9—C11—H11B	109.5	C37—C36—H36A	119.2
H11A—C11—H11B	109.5	C35—C36—H36A	119.2
C9—C11—H11C	109.5	C25—C26—H26A	109.5
H11A—C11—H11C	109.5	C25—C26—H26B	109.5
H11B—C11—H11C	109.5	H26A—C26—H26B	109.5
C6—C7—H7B	109.5	C25—C26—H26C	109.5
C6—C7—H7C	109.5	H26A—C26—H26C	109.5
H7B—C7—H7C	109.5	H26B—C26—H26C	109.5
C6—C7—H7D	109.5	C28—C30—H30A	109.5
H7B—C7—H7D	109.5	C28—C30—H30B	109.5
H7C—C7—H7D	109.5	H30A—C30—H30B	109.5
C16—C15—C14	121.7 (3)	C28—C30—H30C	109.5
C16—C15—H15A	119.1	H30A—C30—H30C	109.5
C14—C15—H15A	119.1	H30B—C30—H30C	109.5
O5—C9—O4	104.4 (2)	C36—C37—C32	119.2 (3)
O5—C9—C11	108.8 (3)	C36—C37—H37A	120.4
O4—C9—C11	108.5 (3)	C32—C37—H37A	120.4
O5—C9—C10	110.9 (3)	C34—C33—C32	119.3 (2)
O4—C9—C10	110.8 (3)	C34—C33—H33A	120.3
C11—C9—C10	113.2 (3)	C32—C33—H33A	120.3
C9—C10—H10A	109.5	C28—C29—H29A	109.5
C9—C10—H10B	109.5	C28—C29—H29B	109.5
H10A—C10—H10B	109.5	H29A—C29—H29B	109.5
C9—C10—H10C	109.5	C28—C29—H29C	109.5
H10A—C10—H10C	109.5	H29A—C29—H29C	109.5
H10B—C10—H10C	109.5	H29B—C29—H29C	109.5
C16—C19—H19A	109.5	C35—C38—H38A	109.5
C16—C19—H19B	109.5	C35—C38—H38B	109.5
H19A—C19—H19B	109.5	H38A—C38—H38B	109.5
C16—C19—H19C	109.5	C35—C38—H38C	109.5
H19A—C19—H19C	109.5	H38A—C38—H38C	109.5
H19B—C19—H19C	109.5	H38B—C38—H38C	109.5
O16—S2—O15	118.05 (14)	C1—O1—C5	114.93 (18)
O16—S2—O14	108.29 (12)	O1—C5—C4	110.5 (2)
O15—S2—O14	109.45 (15)	O1—C5—H5A	109.5
O16—S2—C32	110.89 (12)	C4—C5—H5A	109.5
O15—S2—C32	110.16 (14)	O1—C5—H5B	109.5
O14—S2—C32	98.14 (11)	C4—C5—H5B	109.5
C21—O11—C25	106.47 (17)	H5A—C5—H5B	108.1

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O13i	0.98	2.70	3.358 (3)	125
C4—H4A···C17i	0.98	2.83	3.657 (5)	142
C21—H21A···O3ii	0.98	2.58	3.456 (3)	149
C23—H23A···O16ii	0.98	2.62	3.466 (3)	145
C23—H23A···C33ii	0.98	2.89	3.738 (4)	145
C37—H37A···O8	0.93	2.61	3.341 (4)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O13i	0.98	2.70	3.358 (3)	125
C4—H4A⋯C17i	0.98	2.83	3.657 (5)	142
C21—H21A⋯O3ii	0.98	2.58	3.456 (3)	149
C23—H23A⋯O16ii	0.98	2.62	3.466 (3)	145
C23—H23A⋯C33ii	0.98	2.89	3.738 (4)	145
C37—H37A⋯O8	0.93	2.61	3.341 (4)	136

Symmetry codes: (i) ; (ii) .