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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3097.
Published online 2010 November 6. doi:  10.1107/S1600536810044582
PMCID: PMC3011573

2,3:4,5-Di-O-isopropyl­idenefructos-1-yl p-toluene­sulfonate

Abstract

The title compound, C19H26O8S, has been synthesized from 2,3:4,5-di-O-isopropyl­idene-β-d-fructopyran­ose. The absolute configuration of the fused ring is confirmed by anomalous dispersion effects in the diffraction measurement. The six-membered β-fructopyran­ose ring has a twist-boat conformation with the two five-membered rings trans to each other. In the crystal, inter­molecular non-classical C—H(...)O hydrogen bonds link the mol­ecules into a three-dimensional network.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-66-o3097-scheme1.jpg

Experimental

Crystal data

  • C19H26O8S
  • M r = 414.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3097-efi1.jpg
  • 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 [triangle]), 3010 Friedel pairs
  • Flack parameter: −0.02 (5)

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

We thank Dr Yang Li for his help during the refinement.

supplementary crystallographic information

Comment

As we know, p-toluenesulfonyl group has been extensively approved as a good substituent group for a long time. A series of derivatives can be synthesized by the substituent reaction of the title compound (Reitz et al., 1989; Dekany et al., 2007). Furthermore, in our study we found that it also can easily react with pyrrole which will be one effective approach to synthesize the corresponding novel N-carbohydrate-derived pyrrole compound. The molecular and crystal structure is helpful to confirm the absolute configuration of the fused ring in the derivatives of the title compound.

In the title compound, as shown at Fig. 1, the pyranose ring adopts a twist boat conformation. This conformation is the result of distortion introduced by the fusion of one six- and two five-membered rings. All bond lengths and angles of this part are normal and comparable with those reported for the related structure (Lis & Weichsel, 1987). In the crystal, weak C—H···O non-classical H bonds (Table 1) link the molecules into a three-dimensional network.

Experimental

The title compound was prepared according to literature (Reitz et al., 1989). The product (1 g) was dissolved in ethyl ether (25 ml) and hexane (25 ml). Single crystals suitable for X-ray diffraction experiment were obtained from the solution by cooling at 255 K for three days.

The molecule is characterized by NMR (Fig. 2). 1H NMR (CDCl3, 400 MHz): δ 7.79 (2H, d, J = 8.2 Hz, H-11, H-11'), 7.34 (2H, d, J = 8.2 Hz, H-12, H-12'), 4.56 (1H, dd, J = 7.9 Hz, J = 2.5 Hz, H-4), 4.30 (1H, d, J = 2.5 Hz, H-5), 4.20 (1H, d, J = 7.9 Hz, H-3), 4.07 (1H, d, J = 10.3 Hz, H-1a), 4.01 (1H, d, J = 10.3 Hz, H-1b), 3.86 (1H, d, J = 12.8 Hz, H-6a), 3.80(1H, d, J = 12.8 Hz, H-6b), 2.44 (3H, s, H-14), 1.50, 1.36, 1.31 (3H, 6H, 3H, CH3-7, CH3-7', CH3-8, CH3-8').

13C NMR(CDCl3, 100 MHz): δ 144.97 (C-10), 132.51(C-13), 129.84 (C-12, C-12'), 128.14 (C-11, C-11'), 109.18, 109.04 (C-9, C-9'), 100.67 (C-2), 70.59 (C-3), 69.90 (C-4, C-5), 69.04 (C-1), 61.26 (C-6), 26.44, 25.72, 25.17, 23.99 (CH3-7, CH3-7', CH3-8, CH3-8'), 21.62 (C-14).

HRMS(ES+): m/z [M+Na]+ calcd. for C19H26O8SNa: 437.1246; found: 437.1261.

Refinement

All H atoms attached to C atoms were treated as riding, with C—H = 0.9700Å for methylene group, C—H = 0.9800Å for methyne group and C—H = 0.9600Å for methyl group, with Uiso(H) = 1.2Ueq(C) of the carrier atoms to which they are attached and Uiso(H) = 1.5Ueq(C) for the methyl groups. The number of Friedel pairs is 3010 which is determined by the difference between the number of unique reflections used in SHELXL when a 'MERG 2' and 'MERG 3' instruction were used.

Figures

Fig. 1.
The structure of two molecules of title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
Fig. 2.
The structure of title compound, with atoms labeling corresponding to the characterization by 1H NMR and 13C NMR.

Crystal data

C19H26O8SF(000) = 880
Mr = 414.47Dx = 1.300 Mg m3
Monoclinic, P21Melting point: 357 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 13.870 (5) ÅCell parameters from 4356 reflections
b = 10.153 (4) Åθ = 2.4–23.0°
c = 15.715 (6) ŵ = 0.19 mm1
β = 106.831 (4)°T = 273 K
V = 2118.2 (14) Å3Block, colourless
Z = 40.43 × 0.36 × 0.27 mm

Data collection

Bruker SMART APEX CCD diffractometer6040 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
graphiteθmax = 25.0°, θmin = 2.3°
[var phi]– and ω–scansh = −16→9
10503 measured reflectionsk = −12→12
6948 independent reflectionsl = −18→18

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034w = 1/[σ2(Fo2) + (0.0498P)2 + 0.015P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.15 e Å3
6948 reflectionsΔρmin = −0.19 e Å3
506 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
13 restraintsExtinction coefficient: 0.0092 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 3010 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.02 (5)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.24587 (4)0.18747 (6)0.02021 (4)0.05469 (18)
O30.19989 (12)−0.26856 (17)0.18097 (10)0.0516 (4)
O20.15726 (12)−0.22131 (18)0.03390 (10)0.0503 (4)
O60.22579 (12)0.04415 (17)0.05015 (11)0.0543 (4)
O50.50852 (14)−0.3218 (2)0.16864 (15)0.0765 (6)
C10.25987 (17)−0.1891 (2)0.06751 (16)0.0449 (5)
O40.45357 (13)−0.1488 (2)0.23044 (13)0.0684 (5)
C20.27894 (17)−0.1881 (3)0.16876 (15)0.0469 (6)
H2A0.2720−0.09820.18900.056*
C130.36794 (17)0.2246 (2)0.08676 (16)0.0469 (6)
C120.2830 (2)−0.0621 (3)0.02666 (18)0.0558 (7)
H12A0.3545−0.04300.04850.067*
H12B0.2652−0.0710−0.03750.067*
C140.4482 (2)0.2255 (3)0.05212 (18)0.0602 (7)
H14A0.43930.2034−0.00710.072*
C30.37782 (19)−0.2460 (3)0.22273 (17)0.0554 (6)
H3A0.3737−0.27050.28190.066*
C80.0499 (2)−0.1399 (3)0.11720 (18)0.0591 (7)
H8A0.0892−0.06060.12900.089*
H8B0.0236−0.15810.16620.089*
H8C−0.0049−0.12890.06390.089*
O80.17471 (14)0.26665 (19)0.04647 (15)0.0734 (6)
O70.24594 (14)0.1835 (2)−0.06986 (12)0.0739 (5)
C60.11497 (18)−0.2526 (3)0.10546 (15)0.0482 (6)
C40.4142 (2)−0.3638 (3)0.1795 (2)0.0619 (7)
H4A0.4240−0.44080.21860.074*
C180.3815 (2)0.2560 (3)0.17503 (18)0.0604 (7)
H18A0.32720.25490.19850.073*
C160.5571 (2)0.2930 (3)0.1936 (2)0.0713 (8)
C170.4754 (2)0.2886 (3)0.2274 (2)0.0702 (8)
H17A0.48470.30830.28700.084*
C110.6036 (3)−0.1244 (4)0.1876 (3)0.0982 (12)
H11A0.5631−0.09630.13000.147*
H11B0.6621−0.16970.18180.147*
H11C0.6241−0.04910.22540.147*
C70.0593 (2)−0.3813 (3)0.0869 (2)0.0660 (7)
H7B0.1044−0.44940.07990.099*
H7C0.0045−0.37390.03340.099*
H7D0.0335−0.40290.13560.099*
C150.5421 (2)0.2597 (3)0.1066 (2)0.0726 (8)
H15A0.59670.26010.08340.087*
C90.5432 (2)−0.2156 (3)0.2276 (2)0.0689 (8)
C100.6013 (3)−0.2650 (5)0.3194 (2)0.1077 (14)
H10A0.5595−0.32350.34110.162*
H10B0.6208−0.19150.35910.162*
H10C0.6605−0.31110.31580.162*
C190.6594 (3)0.3360 (5)0.2510 (3)0.1266 (17)
H19A0.70680.33260.21700.190*
H19B0.68120.27820.30130.190*
H19C0.65530.42450.27120.190*
S20.20695 (5)0.40282 (6)0.37302 (5)0.05712 (18)
O110.02664 (12)0.86733 (17)0.33953 (11)0.0502 (4)
O100.03125 (11)0.70729 (17)0.44201 (10)0.0522 (4)
O130.29576 (12)0.88143 (16)0.38639 (11)0.0529 (4)
C220.19864 (19)0.9338 (2)0.37952 (16)0.0453 (6)
H22A0.17790.99440.32890.054*
O90.17593 (13)0.80561 (16)0.53013 (10)0.0518 (4)
O140.15205 (17)0.53361 (18)0.38479 (14)0.0729 (6)
O160.24890 (14)0.34602 (18)0.45814 (13)0.0661 (5)
C320.1013 (2)0.3142 (2)0.31216 (17)0.0509 (6)
C240.1586 (2)0.9447 (2)0.52606 (17)0.0549 (6)
H24A0.18230.98180.58540.066*
H24B0.08700.96190.50320.066*
O120.31802 (15)1.0050 (2)0.50883 (13)0.0710 (6)
C280.3671 (2)0.9641 (3)0.4459 (2)0.0602 (7)
C310.1972 (2)0.6168 (2)0.46030 (17)0.0509 (6)
H31A0.26560.63960.46170.061*
H31B0.19910.57170.51510.061*
C25−0.03423 (18)0.7689 (3)0.36376 (16)0.0541 (6)
C210.12717 (17)0.8185 (2)0.36592 (15)0.0407 (5)
H21A0.13780.76030.31970.049*
C200.13331 (17)0.7389 (2)0.45007 (15)0.0428 (5)
C34−0.0497 (2)0.1991 (3)0.30565 (18)0.0626 (7)
H34A−0.09640.16990.33350.075*
C230.2126 (2)1.0091 (2)0.46710 (18)0.0552 (7)
H23A0.19001.10050.45490.066*
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−0.01450.62720.27880.112*
H27B−0.11280.70980.23930.112*
H27C−0.10950.60200.31150.112*
C360.0060 (2)0.2146 (3)0.17747 (19)0.0702 (8)
H36A−0.00270.19550.11780.084*
C26−0.1181 (2)0.8387 (4)0.3889 (2)0.0783 (9)
H26A−0.08990.90200.43480.117*
H26B−0.15710.77560.41030.117*
H26C−0.16060.88300.33780.117*
C300.3934 (3)1.0791 (3)0.3967 (3)0.0906 (11)
H30A0.33341.12760.36800.136*
H30B0.42371.04770.35290.136*
H30C0.43991.13550.43790.136*
C370.0877 (2)0.2872 (3)0.22333 (18)0.0644 (7)
H37A0.13360.31800.19500.077*
C330.0311 (2)0.2706 (3)0.35331 (18)0.0583 (7)
H33A0.03910.29010.41280.070*
C290.4569 (2)0.8816 (4)0.4933 (3)0.0996 (12)
H29A0.43520.80910.52250.149*
H29B0.50390.93460.53660.149*
H29C0.48880.84840.45100.149*
O150.27212 (17)0.4276 (3)0.31983 (16)0.0931 (7)
C38−0.1524 (2)0.0859 (3)0.1661 (2)0.0852 (10)
H38A−0.14980.07520.10610.128*
H38B−0.21420.12880.16570.128*
H38C−0.14930.00100.19380.128*
O10.31903 (13)−0.28041 (18)0.03724 (11)0.0568 (5)
C50.3453 (2)−0.3965 (3)0.09017 (19)0.0605 (7)
H5A0.3779−0.45870.06070.073*
H5B0.2847−0.43760.09680.073*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0471 (3)0.0582 (4)0.0548 (4)−0.0019 (3)0.0085 (3)0.0117 (3)
O30.0432 (9)0.0706 (11)0.0399 (9)0.0006 (8)0.0103 (7)0.0064 (8)
O20.0449 (9)0.0692 (11)0.0350 (8)−0.0111 (8)0.0090 (7)0.0003 (8)
O60.0482 (10)0.0558 (10)0.0632 (11)−0.0051 (8)0.0230 (9)0.0019 (9)
O50.0488 (10)0.0854 (13)0.0957 (14)0.0052 (11)0.0212 (10)−0.0239 (13)
C10.0411 (13)0.0530 (13)0.0404 (13)−0.0054 (11)0.0116 (11)−0.0050 (11)
O40.0443 (10)0.0787 (12)0.0768 (13)−0.0029 (10)0.0092 (9)−0.0219 (11)
C20.0422 (13)0.0572 (14)0.0406 (13)−0.0010 (11)0.0110 (11)−0.0050 (11)
C130.0473 (13)0.0458 (12)0.0473 (14)−0.0002 (11)0.0134 (11)0.0086 (11)
C120.0537 (15)0.0609 (16)0.0583 (16)−0.0078 (13)0.0250 (13)−0.0027 (13)
C140.0586 (16)0.0715 (17)0.0536 (15)−0.0091 (14)0.0213 (13)−0.0044 (13)
C30.0441 (14)0.0722 (17)0.0483 (14)0.0015 (13)0.0110 (12)−0.0030 (13)
C80.0523 (15)0.0699 (17)0.0530 (16)0.0053 (13)0.0119 (13)0.0028 (13)
O80.0530 (11)0.0685 (12)0.0960 (15)0.0122 (10)0.0171 (11)0.0076 (11)
O70.0712 (12)0.0898 (14)0.0535 (11)−0.0101 (12)0.0065 (9)0.0123 (11)
C60.0455 (13)0.0599 (14)0.0380 (13)−0.0044 (11)0.0101 (11)0.0040 (11)
C40.0549 (16)0.0600 (16)0.0679 (19)0.0063 (13)0.0130 (14)0.0035 (14)
C180.0576 (16)0.0723 (18)0.0554 (16)0.0026 (14)0.0227 (14)0.0001 (14)
C160.0549 (17)0.0755 (19)0.076 (2)−0.0036 (15)0.0064 (15)−0.0147 (17)
C170.0691 (19)0.083 (2)0.0536 (17)0.0049 (17)0.0095 (15)−0.0107 (16)
C110.067 (2)0.118 (3)0.112 (3)−0.018 (2)0.030 (2)−0.021 (2)
C70.0628 (17)0.0686 (16)0.0664 (18)−0.0136 (14)0.0186 (15)0.0019 (15)
C150.0513 (16)0.089 (2)0.082 (2)−0.0105 (15)0.0273 (16)−0.0107 (18)
C90.0438 (15)0.088 (2)0.071 (2)0.0067 (15)0.0112 (14)−0.0128 (17)
C100.0609 (19)0.164 (4)0.086 (3)0.014 (2)0.0016 (18)0.005 (3)
C190.060 (2)0.160 (4)0.139 (4)−0.012 (3)−0.004 (2)−0.052 (3)
S20.0620 (4)0.0451 (3)0.0663 (4)0.0042 (3)0.0219 (3)−0.0012 (3)
O110.0450 (9)0.0576 (10)0.0464 (10)0.0058 (8)0.0108 (8)0.0128 (8)
O100.0472 (9)0.0647 (11)0.0468 (9)−0.0001 (8)0.0168 (8)0.0141 (8)
O130.0489 (10)0.0476 (9)0.0644 (11)−0.0047 (8)0.0197 (9)−0.0083 (8)
C220.0530 (15)0.0384 (13)0.0446 (14)0.0023 (11)0.0144 (12)0.0041 (10)
O90.0688 (11)0.0470 (9)0.0364 (9)0.0030 (8)0.0099 (8)−0.0003 (7)
O140.0850 (14)0.0445 (10)0.0727 (13)0.0137 (10)−0.0032 (11)−0.0102 (9)
O160.0684 (9)0.0575 (8)0.0679 (9)0.0060 (7)0.0124 (7)0.0032 (7)
C320.0615 (16)0.0379 (12)0.0535 (16)0.0074 (11)0.0168 (13)−0.0010 (11)
C240.0666 (17)0.0492 (14)0.0492 (15)0.0100 (13)0.0173 (13)−0.0109 (12)
O120.0608 (12)0.0828 (13)0.0628 (13)−0.0097 (11)0.0076 (10)−0.0204 (11)
C280.0566 (17)0.0554 (15)0.0662 (18)−0.0076 (13)0.0143 (15)−0.0122 (14)
C310.0577 (15)0.0418 (12)0.0502 (15)0.0016 (11)0.0110 (13)0.0013 (11)
C250.0476 (14)0.0702 (17)0.0444 (14)−0.0033 (13)0.0134 (12)0.0087 (13)
C210.0453 (13)0.0428 (12)0.0353 (13)0.0031 (10)0.0138 (11)0.0004 (10)
C200.0506 (13)0.0408 (11)0.0386 (13)0.0001 (10)0.0154 (11)0.0017 (10)
C340.0614 (16)0.0693 (17)0.0581 (17)−0.0007 (15)0.0191 (14)0.0040 (15)
C230.0682 (18)0.0345 (12)0.0623 (18)0.0064 (12)0.0182 (15)−0.0082 (12)
C350.0672 (17)0.0543 (14)0.0536 (17)0.0073 (14)0.0038 (14)0.0042 (14)
C270.0708 (18)0.095 (2)0.0569 (17)−0.0270 (18)0.0178 (14)−0.0003 (17)
C360.090 (2)0.0724 (19)0.0467 (16)0.0062 (17)0.0179 (15)−0.0027 (14)
C260.0535 (17)0.115 (3)0.0705 (19)0.0194 (17)0.0243 (15)0.0182 (18)
C300.093 (3)0.069 (2)0.115 (3)−0.0268 (19)0.040 (2)−0.009 (2)
C370.083 (2)0.0616 (16)0.0538 (17)0.0050 (16)0.0291 (16)0.0006 (14)
C330.0658 (17)0.0652 (17)0.0467 (14)0.0042 (14)0.0208 (14)−0.0026 (13)
C290.060 (2)0.118 (3)0.109 (3)0.014 (2)0.0061 (19)0.005 (2)
O150.0874 (16)0.1010 (17)0.1040 (17)−0.0210 (14)0.0486 (14)−0.0096 (14)
C380.076 (2)0.081 (2)0.081 (2)−0.0033 (18)−0.0042 (18)−0.0040 (18)
O10.0623 (11)0.0611 (11)0.0511 (10)0.0026 (9)0.0232 (9)−0.0106 (9)
C50.0624 (18)0.0503 (15)0.0724 (19)0.0027 (13)0.0254 (16)−0.0076 (14)

Geometric parameters (Å, °)

S1—O71.416 (2)S2—C321.749 (3)
S1—O81.424 (2)O11—C211.424 (3)
S1—O61.5786 (19)O11—C251.429 (3)
S1—C131.754 (3)O10—C201.421 (3)
O3—C61.419 (3)O10—C251.443 (3)
O3—C21.424 (3)O13—C281.422 (3)
O2—C11.406 (3)O13—C221.423 (3)
O2—C61.446 (3)C22—C211.509 (3)
O6—C121.449 (3)C22—C231.537 (4)
O5—C91.413 (4)C22—H22A0.9800
O5—C41.432 (3)O9—C201.400 (3)
C1—O11.409 (3)O9—C241.431 (3)
C1—C121.516 (4)O14—C311.444 (3)
C1—C21.536 (3)C32—C371.381 (4)
O4—C31.420 (3)C32—C331.388 (3)
O4—C91.428 (3)C24—C231.499 (4)
C2—C31.508 (3)C24—H24A0.9700
C2—H2A0.9800C24—H24B0.9700
C13—C141.373 (3)O12—C231.420 (3)
C13—C181.382 (4)O12—C281.416 (3)
C12—H12A0.9700C28—C301.502 (4)
C12—H12B0.9700C28—C291.508 (4)
C14—C151.381 (4)C31—C201.505 (3)
C14—H14A0.9300C31—H31A0.9700
C3—C41.532 (4)C31—H31B0.9700
C3—H3A0.9800C25—C271.503 (4)
C8—C61.502 (4)C25—C261.510 (4)
C8—H8A0.9600C21—C201.531 (3)
C8—H8B0.9600C21—H21A0.9800
C8—H8C0.9600C34—C331.363 (4)
C6—C71.503 (4)C34—C351.373 (4)
C4—C51.490 (4)C34—H34A0.9300
C4—H4A0.9800C23—H23A0.9800
C18—C171.364 (4)C35—C361.384 (4)
C18—H18A0.9300C35—C381.514 (4)
C16—C151.365 (4)C27—H27A0.9600
C16—C171.384 (4)C27—H27B0.9600
C16—C191.509 (4)C27—H27C0.9600
C17—H17A0.9300C36—C371.370 (4)
C11—C91.502 (5)C36—H36A0.9300
C11—H11A0.9600C26—H26A0.9600
C11—H11B0.9600C26—H26B0.9600
C11—H11C0.9600C26—H26C0.9600
C7—H7B0.9600C30—H30A0.9600
C7—H7C0.9600C30—H30B0.9600
C7—H7D0.9600C30—H30C0.9600
C15—H15A0.9300C37—H37A0.9300
C9—C101.519 (5)C33—H33A0.9300
C10—H10A0.9600C29—H29A0.9600
C10—H10B0.9600C29—H29B0.9600
C10—H10C0.9600C29—H29C0.9600
C19—H19A0.9600C38—H38A0.9600
C19—H19B0.9600C38—H38B0.9600
C19—H19C0.9600C38—H38C0.9600
S2—O161.418 (2)O1—C51.428 (3)
S2—O151.420 (2)C5—H5A0.9700
S2—O141.568 (2)C5—H5B0.9700
O7—S1—O8120.45 (13)C20—O10—C25110.05 (16)
O7—S1—O6108.85 (12)C28—O13—C22106.98 (18)
O8—S1—O6103.72 (11)O13—C22—C21106.82 (17)
O7—S1—C13108.79 (12)O13—C22—C23104.3 (2)
O8—S1—C13109.66 (12)C21—C22—C23114.8 (2)
O6—S1—C13104.10 (10)O13—C22—H22A110.2
C6—O3—C2107.86 (17)C21—C22—H22A110.2
C1—O2—C6110.70 (17)C23—C22—H22A110.2
C12—O6—S1116.95 (14)C20—O9—C24114.55 (18)
C9—O5—C4107.4 (2)C31—O14—S2118.85 (17)
O2—C1—O1110.23 (19)C37—C32—C33120.0 (3)
O2—C1—C12110.8 (2)C37—C32—S2120.1 (2)
O1—C1—C12101.59 (17)C33—C32—S2119.9 (2)
O2—C1—C2104.05 (17)O9—C24—C23110.54 (19)
O1—C1—C2114.3 (2)O9—C24—H24A109.5
C12—C1—C2116.0 (2)C23—C24—H24A109.5
C3—O4—C9107.3 (2)O9—C24—H24B109.5
O3—C2—C3108.1 (2)C23—C24—H24B109.5
O3—C2—C1103.14 (18)H24A—C24—H24B108.1
C3—C2—C1115.84 (19)C23—O12—C28109.0 (2)
O3—C2—H2A109.8O12—C28—O13104.4 (2)
C3—C2—H2A109.8O12—C28—C30111.6 (2)
C1—C2—H2A109.8O13—C28—C30110.3 (3)
C14—C13—C18120.4 (2)O12—C28—C29108.3 (3)
C14—C13—S1121.2 (2)O13—C28—C29108.4 (2)
C18—C13—S1118.40 (19)C30—C28—C29113.4 (3)
O6—C12—C1109.05 (18)O14—C31—C20106.99 (19)
O6—C12—H12A109.9O14—C31—H31A110.3
C1—C12—H12A109.9C20—C31—H31A110.3
O6—C12—H12B109.9O14—C31—H31B110.3
C1—C12—H12B109.9C20—C31—H31B110.3
H12A—C12—H12B108.3H31A—C31—H31B108.6
C13—C14—C15118.9 (3)O11—C25—O10104.82 (18)
C13—C14—H14A120.5O11—C25—C27112.1 (2)
C15—C14—H14A120.5O10—C25—C27109.8 (2)
O4—C3—C2107.9 (2)O11—C25—C26107.5 (2)
O4—C3—C4104.43 (19)O10—C25—C26108.8 (2)
C2—C3—C4114.7 (2)C27—C25—C26113.4 (2)
O4—C3—H3A109.9O11—C21—C22108.62 (18)
C2—C3—H3A109.9O11—C21—C20103.90 (17)
C4—C3—H3A109.9C22—C21—C20114.7 (2)
C6—C8—H8A109.5O11—C21—H21A109.8
C6—C8—H8B109.5C22—C21—H21A109.8
H8A—C8—H8B109.5C20—C21—H21A109.8
C6—C8—H8C109.5O9—C20—O10109.87 (17)
H8A—C8—H8C109.5O9—C20—C31102.71 (18)
H8B—C8—H8C109.5O10—C20—C31111.34 (19)
O3—C6—O2104.48 (17)O9—C20—C21115.11 (19)
O3—C6—C8111.6 (2)O10—C20—C21103.74 (18)
O2—C6—C8108.8 (2)C31—C20—C21114.26 (18)
O3—C6—C7108.6 (2)C33—C34—C35121.9 (3)
O2—C6—C7110.0 (2)C33—C34—H34A119.0
C8—C6—C7113.1 (2)C35—C34—H34A119.0
O5—C4—C5108.3 (2)O12—C23—C24109.5 (2)
O5—C4—C3104.5 (2)O12—C23—C22104.2 (2)
C5—C4—C3112.8 (2)C24—C23—C22112.4 (2)
O5—C4—H4A110.3O12—C23—H23A110.2
C5—C4—H4A110.3C24—C23—H23A110.2
C3—C4—H4A110.3C22—C23—H23A110.2
C17—C18—C13119.3 (2)C34—C35—C36117.9 (3)
C17—C18—H18A120.3C34—C35—C38121.5 (3)
C13—C18—H18A120.3C36—C35—C38120.6 (3)
C15—C16—C17118.2 (3)C25—C27—H27A109.5
C15—C16—C19121.0 (3)C25—C27—H27B109.5
C17—C16—C19120.8 (3)H27A—C27—H27B109.5
C18—C17—C16121.4 (3)C25—C27—H27C109.5
C18—C17—H17A119.3H27A—C27—H27C109.5
C16—C17—H17A119.3H27B—C27—H27C109.5
C9—C11—H11A109.5C37—C36—C35121.6 (3)
C9—C11—H11B109.5C37—C36—H36A119.2
H11A—C11—H11B109.5C35—C36—H36A119.2
C9—C11—H11C109.5C25—C26—H26A109.5
H11A—C11—H11C109.5C25—C26—H26B109.5
H11B—C11—H11C109.5H26A—C26—H26B109.5
C6—C7—H7B109.5C25—C26—H26C109.5
C6—C7—H7C109.5H26A—C26—H26C109.5
H7B—C7—H7C109.5H26B—C26—H26C109.5
C6—C7—H7D109.5C28—C30—H30A109.5
H7B—C7—H7D109.5C28—C30—H30B109.5
H7C—C7—H7D109.5H30A—C30—H30B109.5
C16—C15—C14121.7 (3)C28—C30—H30C109.5
C16—C15—H15A119.1H30A—C30—H30C109.5
C14—C15—H15A119.1H30B—C30—H30C109.5
O5—C9—O4104.4 (2)C36—C37—C32119.2 (3)
O5—C9—C11108.8 (3)C36—C37—H37A120.4
O4—C9—C11108.5 (3)C32—C37—H37A120.4
O5—C9—C10110.9 (3)C34—C33—C32119.3 (2)
O4—C9—C10110.8 (3)C34—C33—H33A120.3
C11—C9—C10113.2 (3)C32—C33—H33A120.3
C9—C10—H10A109.5C28—C29—H29A109.5
C9—C10—H10B109.5C28—C29—H29B109.5
H10A—C10—H10B109.5H29A—C29—H29B109.5
C9—C10—H10C109.5C28—C29—H29C109.5
H10A—C10—H10C109.5H29A—C29—H29C109.5
H10B—C10—H10C109.5H29B—C29—H29C109.5
C16—C19—H19A109.5C35—C38—H38A109.5
C16—C19—H19B109.5C35—C38—H38B109.5
H19A—C19—H19B109.5H38A—C38—H38B109.5
C16—C19—H19C109.5C35—C38—H38C109.5
H19A—C19—H19C109.5H38A—C38—H38C109.5
H19B—C19—H19C109.5H38B—C38—H38C109.5
O16—S2—O15118.05 (14)C1—O1—C5114.93 (18)
O16—S2—O14108.29 (12)O1—C5—C4110.5 (2)
O15—S2—O14109.45 (15)O1—C5—H5A109.5
O16—S2—C32110.89 (12)C4—C5—H5A109.5
O15—S2—C32110.16 (14)O1—C5—H5B109.5
O14—S2—C3298.14 (11)C4—C5—H5B109.5
C21—O11—C25106.47 (17)H5A—C5—H5B108.1

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3A···O13i0.982.703.358 (3)125
C4—H4A···C17i0.982.833.657 (5)142
C21—H21A···O3ii0.982.583.456 (3)149
C23—H23A···O16ii0.982.623.466 (3)145
C23—H23A···C33ii0.982.893.738 (4)145
C37—H37A···O80.932.613.341 (4)136

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2243).

References

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  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Hirst, E. L., Mitchelle, W. E. A., Percival, E. E. & Percival, E. G. V. (1953). J. Chem. Soc. pp. 3170–3175.
  • Lis, T. & Weichsel, A. (1987). Acta Cryst. C43, 1954–1956.
  • Reitz, A. R., Tuman, R. W., Marchione, C. S., Jordan, A. D. Jr, Bowden, C. R. & Maryanoff, B. E. (1989). J. Med. Chem.32, 2110–2116. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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