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The title compound, C29H36O10·2C2H6OS, forms a monoclinic crystal containing two hydrogen-bonded di­methyl sulfoxide mol­ecules per 10-de­acetyl baccatin III. The lattice is further stabilized by two additional hydrogen bonds and a dipole-dipole interaction. A comparison of 10-de­acetyl baccatin III with the structurally similar docetaxel reveals differences primarily in the benzoyl moiety, while comparisons to baccatin III identify relative differences principally in the cyclo­octane- and cyclo­hexane-ring conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011781/da1143sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011781/da1143Isup2.hkl
Contains datablock I

CCDC reference: 158250

Comment top

The success of paclitaxel and docetaxel (also known as taxol and taxotere, respectively) as anticancer drugs has prompted study of the crystal structures of these and related taxanes. These studies have revealed the structures of both paclitaxel (Mastropaolo et al., 1995) and docetaxel (Gueritte-Voegelein et al., 1990) as well as 2-carbamate taxol (Gao & Golik, 1995), baccatin V (Castellano & Hodder, 1973), 7-mesylpaclitaxel (Gao & Chen, 1996), baccatin III (Gabetta et al., 1995) and 10-deacetyl-7-epitaxol (Gao & Parker, 1996) which share a common tetracyclic ring structure and substitution pattern with paclitaxcel and docetaxel. However, no studies have yet appeared describing the crystal structure of 10-deacetyl baccatin III used in the semi-synthetic production of both paclitaxel and docetaxel. In addition baccatin III derivatives display unusual reactivity as a result of a congested tertiary structure. A description of the structure of 10-deacetyl baccatin III, (I), is therefore of interest. \sch

A crystal of 10-deacetyl baccatin III serendipitously appeared upon evaporation of a dimethyl sulfoxide (DMSO) solution under vacuum. The crystal was of sufficient quality to be subjected to X-ray analysis. The solid obtained contains two DMSO molecules acting as hydrogen-bond acceptors to the hydroxy H atoms at O1 and O7 (Figure 1). Hydrogen-bonding data are given in Table 2. Disorder is observed in the DMSO molecule which is hydrogen-bonded to O1 and consists primarily of inversion about the sulfur atom. Refinement of this DMSO found an approximately 2:1 occupancy of the B and C forms, respectively. This disorder is expected to cause a corresponding change in the H1—O1—C1—C2 dihedral angle due to H1 following the oxygen of DMSO from one form to another. This subtle change is not discernable in the position of the O1 atom and is not expected for the H1 as the present study would be insensitive to the motion of a hydrogen atom. However, previous work (Harper & Grant, 2000) suggests that the difference may be important in solid-state NMR analyses currently being pursued in our laboratory. The OH at position C13 serves as a hydrogen-bond donor to the C9 carbonyl in a neighboring molecule. The C9 carbonyl additionally forms a weak intramolecular hydrogen bond with the OH at C10. The carbonyl of the benzoyl moiety in an adjacent molecule and the S1A sulfur of the DMSO appear to interact via an intermolecular electrostatic dipole-dipole interaction [S1A···O21 = 3.265 (5) Å (2 - x, 1/2 + y, 1 - z), O1A—S1A···O21 = 170.3 (4)°]. This type of electrostatic interaction suggests an additional possible role for the benzoyl group in the bioactivity of taxanes.

The present analysis also identifies differences in 10-deacetyl baccatin III relative to the related compounds docetaxel and baccatin III. Docetaxel differs most significant from 10-deacetyl baccatin III in the relative orientation of the benzoyl's carboxyl and benzene groups. Deviations from co-planarity, as found in docetaxel, are likely to be costly in terms of π-electron delocalization. This study, in conjunction with the earlier studies on related derivatives, establishes that the benzoyl group exhibits an unexpected conformational flexibility that may be relevant to the bioactivity of taxanes.

The structure of 10-deacetyl baccatin III also differs from the most closely related analog, baccatin III, primarily in the cyclooctane and cyclohexane rings. Most significantly, eight corresponding dihedral angles differ by more than 7° [with three of these (C3—C2—C1—O1, C5—C6—C7—C8, and C7—C6—C5—O5) differing by nearly 10°]. Accompanying these differences are significantly shorter bond lengths at C6—C7 and C9—C10 of 10-deacetyl baccatin III. The observation of a shorter C9—C10 bond length in 10-deacetyl baccatin III (1.523 Å versus 1.580 Å in baccatin III) supports Gabetta's contention (Gabetta et al., 1995) that `···linear strain in baccatin III derivatives is affected by acylation···'.

Experimental top

Crystals of 10-deacetyl baccatin III were obtained by vacuum evaporation (200 mm H g) of a dimethyl sulfoxide solution.

Refinement top

All non-hydrogen atoms were refined anisotropically except for S1C, O1C and C2C. These disordered atoms were assigned to the disordered DMSO of lower occupancy. Hydroxy H atoms were located in a difference map and their isotropic displacement parameters were refined. All other H atoms were refined using a riding model and equivalent isotropic parameters selected to correspond with their adjacent carbons (1.5 x Ueq for methyl H atoms, 1.2 x Ueq for the remaining H atoms). H atoms of the disordered DMSO molecule were not included in the refinement.

Computing details top

Data collection: Bruker Software; cell refinement: Bruker Software; data reduction: Bruker Software; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 1994); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound showing the atom-numbering scheme and 40% probability displacement ellipsoids. The disordered DMSO molecule with lower occupancy is not shown.
(I) top
Crystal data top
C29H36O10·2C2H6OSF(000) = 748
Mr = 700.83Dx = 1.327 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.3677 (10) ÅCell parameters from 35 reflections
b = 21.991 (4) Åθ = 7–17°
c = 9.4564 (11) ŵ = 0.21 mm1
β = 115.827 (9)°T = 293 K
V = 1753.5 (4) Å3Block, colorless
Z = 20.5 × 0.4 × 0.3 mm
Data collection top
Bruker P4
diffractometer
θmax = 27.5°, θmin = 1.9°
θ–2θ var. scansh = 012
4342 measured reflectionsk = 028
4103 independent reflectionsl = 1111
3005 reflections with I > 2σ(I)3 standard reflections every 97 reflections
Rint = 0.025 intensity decay: <2.0
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: fullCalculated w = 1/[σ2(Fo2) + (0.0775P)2 + 0.4816P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.056(Δ/σ)max < 0.001
wR(F2) = 0.136Δρmax = 0.34 e Å3
4100 reflectionsΔρmin = 0.26 e Å3
436 parametersAbsolute structure: Flack (1983)
1 restraintAbsolute structure parameter: 0.08 (15)
Crystal data top
C29H36O10·2C2H6OSV = 1753.5 (4) Å3
Mr = 700.83Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.3677 (10) ŵ = 0.21 mm1
b = 21.991 (4) ÅT = 293 K
c = 9.4564 (11) Å0.5 × 0.4 × 0.3 mm
β = 115.827 (9)°
Data collection top
Bruker P4
diffractometer
Rint = 0.025
4342 measured reflections3 standard reflections every 97 reflections
4103 independent reflections intensity decay: <2.0
3005 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136Δρmax = 0.34 e Å3
4100 reflectionsΔρmin = 0.26 e Å3
436 parametersAbsolute structure: Flack (1983)
1 restraintAbsolute structure parameter: 0.08 (15)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.6310 (5)0.2074 (2)0.5046 (5)0.0420 (10)
O10.5923 (5)0.2701 (2)0.4835 (4)0.0581 (9)
H10.50230.28010.39930.09 (2)*
C20.7822 (5)0.2068 (2)0.6661 (5)0.0347 (8)
H2A0.86180.23390.65870.042*
O20.7249 (4)0.23420 (13)0.7725 (3)0.0387 (7)
C30.8626 (4)0.1447 (2)0.7354 (4)0.0314 (8)
H3A0.78560.11330.67580.038*
C40.8916 (5)0.1369 (2)0.9088 (4)0.0348 (8)
O40.7408 (3)0.12433 (13)0.9117 (3)0.0371 (6)
C51.0229 (5)0.0948 (2)1.0202 (5)0.0471 (11)
H5A0.98030.06621.07140.057*
O51.1002 (4)0.1457 (2)1.1240 (4)0.0643 (10)
C61.1288 (6)0.0620 (3)0.9601 (5)0.0535 (12)
H6A1.23320.08041.00680.064*
H6B1.14020.01990.99420.064*
C71.0658 (5)0.0635 (2)0.7829 (5)0.0433 (10)
H7A0.97140.03770.73670.052*
O71.1837 (4)0.0394 (2)0.7427 (4)0.0619 (10)
H71.14030.00660.66980.08 (2)*
C81.0189 (5)0.1297 (2)0.7176 (5)0.0388 (9)
C90.9992 (5)0.1232 (2)0.5467 (5)0.0450 (10)
O91.1078 (4)0.1388 (2)0.5158 (4)0.0676 (11)
C100.8591 (5)0.0907 (2)0.4185 (5)0.0429 (10)
H10A0.86310.04820.45100.052*
O100.8759 (5)0.0910 (2)0.2762 (4)0.0622 (10)
H100.96070.09960.29750.05 (2)*
C110.7007 (5)0.1159 (2)0.3961 (5)0.0438 (11)
C120.5939 (5)0.0800 (2)0.4142 (5)0.0483 (11)
C130.4516 (6)0.1086 (2)0.4266 (6)0.0569 (14)
H13A0.36730.11490.32030.068*
O130.3946 (5)0.0683 (2)0.5089 (7)0.091 (2)
H130.32110.08870.54420.11 (3)*
C140.4945 (6)0.1707 (2)0.5119 (6)0.0494 (11)
H14A0.40020.19590.46930.059*
H14B0.52060.16370.62170.059*
C150.6696 (6)0.1842 (2)0.3691 (5)0.0486 (11)
C160.8019 (3)0.22277 (13)0.3618 (3)0.067 (2)
H16A0.76920.264550.34450.1*
H16B0.82390.208810.27710.1*
H16C0.89580.219170.45910.1*
C170.5242 (3)0.19368 (13)0.2076 (3)0.080 (2)
H17A0.43610.170470.20440.121*
H17B0.55040.180420.12500.121*
H17C0.49650.236020.19380.121*
C180.6025 (3)0.01178 (13)0.4276 (3)0.0646 (15)
H18A0.51210.003140.43970.097*
H18B0.69780.000230.51730.097*
H18C0.60300.005260.33430.097*
C191.1542 (3)0.17542 (13)0.8013 (3)0.0541 (12)
H19A1.17000.180650.90790.081*
H19B1.12710.213800.74770.081*
H19C1.25000.160320.80040.081*
C200.9747 (6)0.1869 (2)1.0293 (5)0.0461 (10)
H20A1.01100.22050.98700.055*
H20B0.91280.20151.08190.055*
C210.7596 (6)0.2922 (2)0.8122 (5)0.0428 (10)
O210.8668 (5)0.3194 (2)0.8025 (5)0.0641 (10)
C220.6525 (6)0.3203 (2)0.8732 (5)0.0474 (11)
C230.5216 (7)0.2909 (2)0.8711 (6)0.0570 (12)
H23A0.49750.25150.83200.068*
C240.4271 (8)0.3200 (3)0.9268 (8)0.073 (2)
H24A0.33690.30050.92210.088*
C250.4636 (9)0.3772 (3)0.9893 (9)0.081 (2)
H25A0.40010.39611.02910.097*
C260.5931 (10)0.4060 (4)0.9927 (12)0.107 (3)
H26A0.61760.44511.03390.129*
C270.6877 (9)0.3781 (3)0.9358 (10)0.086 (2)
H27A0.77660.39820.93940.103*
C280.6907 (6)0.0657 (2)0.8873 (6)0.0517 (12)
O280.7560 (5)0.0266 (2)0.8496 (5)0.0654 (10)
C290.5482 (8)0.0587 (3)0.9171 (9)0.078 (2)
H29A0.52080.09740.94550.118*
H29B0.57060.03031.00110.118*
H29C0.46120.04400.82370.118*
S1A1.0904 (2)0.09297 (7)0.4551 (2)0.0761 (5)
O1A1.0423 (7)0.0562 (3)0.5601 (7)0.103 (2)
C1A1.2993 (10)0.0881 (4)0.5339 (12)0.106 (3)
H1AA1.34630.11190.62810.159*
H1AB1.33150.04640.55770.159*
H1AC1.33360.10320.45850.159*
C2A1.0527 (17)0.0463 (5)0.2950 (13)0.143 (4)
H2AA0.94020.04260.23320.215*
H2AB1.09960.06360.23190.215*
H2AC1.09740.00680.33110.215*
S1B0.1547 (3)0.31854 (11)0.2668 (3)0.0750 (11)0.653 (7)
O1B0.2802 (10)0.2893 (5)0.2377 (9)0.086 (2)0.653 (7)
C1B0.149 (4)0.3937 (10)0.216 (4)0.183 (15)0.653 (7)
C2B0.233 (2)0.3291 (12)0.4790 (17)0.153 (9)0.653 (7)
S1C0.2544 (8)0.3565 (3)0.3366 (8)0.100 (3)*0.347 (7)
O1C0.334 (2)0.3179 (9)0.262 (2)0.087 (5)*0.347 (7)
C1C0.150 (3)0.2998 (11)0.403 (3)0.085 (6)*0.347 (7)
C2C0.106 (4)0.3978 (19)0.206 (4)0.094 (9)*0.347 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.051 (2)0.035 (2)0.038 (2)0.013 (2)0.018 (2)0.001 (2)
O10.083 (3)0.039 (2)0.052 (2)0.020 (2)0.030 (2)0.0108 (15)
C20.044 (2)0.030 (2)0.036 (2)0.001 (2)0.022 (2)0.003 (2)
O20.054 (2)0.0308 (14)0.040 (2)0.0014 (13)0.0279 (14)0.0034 (12)
C30.027 (2)0.036 (2)0.029 (2)0.001 (2)0.0108 (15)0.005 (2)
C40.034 (2)0.041 (2)0.032 (2)0.001 (2)0.016 (2)0.001 (2)
O40.0374 (14)0.038 (2)0.0418 (15)0.0007 (12)0.0227 (12)0.0027 (12)
C50.039 (2)0.062 (3)0.033 (2)0.008 (2)0.009 (2)0.005 (2)
O50.050 (2)0.085 (3)0.037 (2)0.008 (2)0.0010 (14)0.012 (2)
C60.041 (2)0.068 (3)0.044 (2)0.020 (2)0.013 (2)0.006 (2)
C70.031 (2)0.053 (3)0.045 (2)0.007 (2)0.016 (2)0.004 (2)
O70.042 (2)0.079 (3)0.066 (2)0.016 (2)0.024 (2)0.013 (2)
C80.035 (2)0.048 (2)0.035 (2)0.002 (2)0.017 (2)0.009 (2)
C90.048 (2)0.050 (3)0.043 (2)0.009 (2)0.027 (2)0.004 (2)
O90.066 (2)0.093 (3)0.064 (2)0.003 (2)0.047 (2)0.003 (2)
C100.054 (3)0.043 (2)0.034 (2)0.012 (2)0.021 (2)0.003 (2)
O100.075 (3)0.078 (3)0.042 (2)0.012 (2)0.033 (2)0.007 (2)
C110.049 (2)0.049 (3)0.025 (2)0.016 (2)0.007 (2)0.005 (2)
C120.042 (2)0.049 (3)0.043 (2)0.004 (2)0.008 (2)0.012 (2)
C130.037 (2)0.056 (3)0.059 (3)0.005 (2)0.003 (2)0.017 (2)
O130.071 (3)0.062 (3)0.165 (5)0.016 (2)0.073 (3)0.029 (3)
C140.043 (2)0.048 (3)0.051 (3)0.011 (2)0.015 (2)0.003 (2)
C150.064 (3)0.048 (3)0.032 (2)0.012 (2)0.020 (2)0.004 (2)
C160.103 (4)0.053 (3)0.067 (3)0.017 (3)0.058 (3)0.011 (3)
C170.107 (5)0.080 (4)0.035 (3)0.041 (4)0.013 (3)0.007 (3)
C180.061 (3)0.044 (3)0.086 (4)0.002 (2)0.029 (3)0.021 (3)
C190.041 (2)0.068 (3)0.059 (3)0.014 (2)0.027 (2)0.013 (2)
C200.052 (3)0.052 (3)0.033 (2)0.005 (2)0.017 (2)0.010 (2)
C210.058 (3)0.034 (2)0.041 (2)0.000 (2)0.026 (2)0.002 (2)
O210.085 (3)0.043 (2)0.088 (3)0.021 (2)0.059 (2)0.016 (2)
C220.066 (3)0.036 (2)0.046 (2)0.002 (2)0.030 (2)0.004 (2)
C230.070 (3)0.041 (2)0.068 (3)0.002 (2)0.038 (3)0.009 (2)
C240.074 (4)0.070 (4)0.092 (4)0.002 (3)0.052 (3)0.007 (3)
C250.101 (5)0.068 (4)0.103 (5)0.020 (4)0.071 (4)0.009 (4)
C260.132 (7)0.065 (4)0.167 (8)0.022 (4)0.104 (6)0.062 (5)
C270.105 (5)0.051 (3)0.138 (6)0.021 (3)0.088 (5)0.039 (4)
C280.045 (2)0.049 (3)0.060 (3)0.005 (2)0.022 (2)0.003 (2)
O280.070 (2)0.041 (2)0.095 (3)0.003 (2)0.044 (2)0.006 (2)
C290.067 (3)0.068 (4)0.120 (5)0.021 (3)0.059 (4)0.005 (4)
S1A0.0987 (11)0.0532 (8)0.0962 (11)0.0088 (8)0.0609 (10)0.0188 (8)
O1A0.121 (4)0.096 (4)0.131 (5)0.022 (3)0.090 (4)0.039 (3)
C1A0.100 (5)0.083 (5)0.152 (8)0.005 (4)0.070 (6)0.031 (5)
C2A0.217 (12)0.106 (7)0.131 (8)0.065 (8)0.099 (9)0.022 (6)
S1B0.0575 (14)0.0519 (14)0.100 (2)0.0060 (11)0.0199 (12)0.0068 (12)
O1B0.075 (5)0.082 (5)0.081 (5)0.030 (5)0.015 (4)0.014 (4)
C1B0.26 (3)0.082 (11)0.31 (3)0.104 (15)0.22 (3)0.071 (14)
C2B0.116 (11)0.26 (3)0.073 (8)0.075 (15)0.028 (8)0.009 (12)
Geometric parameters (Å, º) top
C1—O11.417 (5)C15—C161.528 (6)
C1—C141.539 (7)C15—C171.555 (5)
C1—C151.561 (6)C21—O211.205 (6)
C1—C21.566 (6)C21—C221.492 (6)
C2—O21.460 (5)C22—C231.379 (7)
C2—C31.561 (6)C22—C271.380 (7)
O2—C211.330 (5)C23—C241.369 (8)
C3—C41.551 (5)C24—C251.368 (10)
C3—C81.579 (5)C25—C261.358 (10)
C4—O41.452 (5)C26—C271.366 (9)
C4—C201.529 (6)C28—O281.196 (6)
C4—C51.532 (6)C28—C291.487 (7)
O4—C281.357 (6)S1A—O1A1.494 (5)
C5—O51.456 (6)S1A—C2A1.734 (11)
C5—C61.523 (7)S1A—C1A1.768 (8)
O5—C201.444 (6)S1B—S1C1.212 (7)
C6—C71.515 (7)S1B—C1C1.38 (3)
C7—O71.418 (5)S1B—O1B1.468 (8)
C7—C81.567 (7)S1B—O1C1.70 (2)
C8—C191.540 (5)S1B—C1B1.72 (2)
C8—C91.551 (6)S1B—C2B1.83 (2)
C9—O91.223 (6)S1B—C2C1.83 (4)
C9—C101.522 (7)O1B—O1C0.78 (2)
C10—O101.421 (5)O1B—S1C1.822 (11)
C10—C111.509 (6)C1B—S1C1.40 (3)
C11—C121.343 (7)C2B—C1C1.02 (3)
C11—C151.530 (7)C2B—S1C1.57 (2)
C12—C181.505 (6)S1C—O1C1.49 (2)
C12—C131.524 (7)S1C—C2C1.67 (4)
C13—O131.428 (8)S1C—C1C1.86 (3)
C13—C141.548 (7)
O1—C1—C14110.5 (4)C26—C25—C24119.5 (6)
O1—C1—C15109.9 (4)C25—C26—C27120.4 (6)
C14—C1—C15111.1 (4)C26—C27—C22120.6 (6)
O1—C1—C2102.2 (3)O28—C28—O4123.4 (4)
C14—C1—C2111.6 (4)O28—C28—C29126.9 (5)
C15—C1—C2111.3 (4)O4—C28—C29109.7 (5)
O2—C2—C3109.1 (3)O1A—S1A—C2A104.7 (4)
O2—C2—C1102.8 (3)O1A—S1A—C1A106.6 (4)
C3—C2—C1118.8 (3)C2A—S1A—C1A95.7 (6)
C21—O2—C2118.1 (3)S1C—S1B—C1C91.7 (11)
C4—C3—C2111.7 (3)S1C—S1B—O1B85.1 (5)
C4—C3—C8110.3 (3)C1C—S1B—O1B113.7 (11)
C2—C3—C8116.0 (3)S1C—S1B—O1C58.9 (8)
O4—C4—C20107.9 (3)C1C—S1B—O1C117.3 (12)
O4—C4—C5111.6 (3)O1B—S1B—O1C27.1 (6)
C20—C4—C585.8 (3)S1C—S1B—C1B54.0 (13)
O4—C4—C3108.5 (3)C1C—S1B—C1B122.9 (14)
C20—C4—C3120.4 (3)O1B—S1B—C1B107.5 (9)
C5—C4—C3120.8 (3)O1C—S1B—C1B85.0 (11)
C28—O4—C4116.4 (3)S1C—S1B—C2B58.0 (9)
O5—C5—C6113.7 (4)C1C—S1B—C2B33.7 (12)
O5—C5—C490.8 (4)O1B—S1B—C2B107.0 (6)
C6—C5—C4119.2 (4)O1C—S1B—C2B95.8 (9)
C20—O5—C591.8 (3)C1B—S1B—C2B97.8 (14)
C7—C6—C5113.5 (4)S1C—S1B—C2C62.7 (11)
O7—C7—C6108.3 (4)C1C—S1B—C2C118.5 (15)
O7—C7—C8111.1 (4)O1B—S1B—C2C117.8 (13)
C6—C7—C8111.4 (4)O1C—S1B—C2C96.4 (14)
C19—C8—C9107.1 (3)C1B—S1B—C2C11.6 (18)
C19—C8—C7112.2 (3)C2B—S1B—C2C98.8 (13)
C9—C8—C7102.2 (3)O1C—O1B—S1B93.2 (16)
C19—C8—C3113.8 (3)O1C—O1B—S1C53.1 (15)
C9—C8—C3115.8 (3)S1B—O1B—S1C41.5 (3)
C7—C8—C3105.4 (3)S1C—C1B—S1B44.3 (7)
O9—C9—C10117.3 (4)C1C—C2B—S1C89.2 (17)
O9—C9—C8119.3 (4)C1C—C2B—S1B48.2 (15)
C10—C9—C8122.9 (4)S1C—C2B—S1B41.0 (5)
O10—C10—C11111.9 (4)S1B—S1C—C1B81.6 (14)
O10—C10—C9109.9 (4)S1B—S1C—O1C77.1 (8)
C11—C10—C9113.2 (3)C1B—S1C—O1C105.6 (13)
C12—C11—C10120.5 (4)S1B—S1C—C2B81.1 (10)
C12—C11—C15120.0 (4)C1B—S1C—C2B127.9 (12)
C10—C11—C15119.2 (4)O1C—S1C—C2B117.6 (11)
C11—C12—C18125.5 (4)S1B—S1C—C2C77.1 (14)
C11—C12—C13119.5 (4)C1B—S1C—C2C10 (2)
C18—C12—C13114.9 (4)O1C—S1C—C2C112.6 (15)
O13—C13—C12109.4 (4)C2B—S1C—C2C118.0 (15)
O13—C13—C14109.7 (4)S1B—S1C—O1B53.4 (4)
C12—C13—C14111.5 (4)C1B—S1C—O1B105.0 (12)
C1—C14—C13118.1 (4)O1C—S1C—O1B24.6 (7)
C16—C15—C11116.9 (4)C2B—S1C—O1B103.0 (10)
C16—C15—C17105.2 (3)C2C—S1C—O1B108.2 (13)
C11—C15—C17108.5 (4)S1B—S1C—C1C47.7 (9)
C16—C15—C1109.7 (4)C1B—S1C—C1C112.2 (15)
C11—C15—C1106.2 (4)O1C—S1C—C1C102.9 (11)
C17—C15—C1110.2 (4)C2B—S1C—C1C33.4 (9)
O5—C20—C491.4 (3)C2C—S1C—C1C103.1 (16)
O21—C21—O2124.3 (4)O1B—S1C—C1C80.6 (9)
O21—C21—C22123.2 (4)O1B—O1C—S1C102.3 (18)
O2—C21—C22112.5 (4)O1B—O1C—S1B59.7 (14)
C23—C22—C27118.8 (5)S1C—O1C—S1B44.1 (6)
C23—C22—C21123.0 (4)C2B—C1C—S1B98 (2)
C27—C22—C21118.1 (5)C2B—C1C—S1C57.5 (17)
C24—C23—C22119.8 (5)S1B—C1C—S1C40.6 (7)
C25—C24—C23120.9 (6)S1C—C2C—S1B40.2 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1B0.90 (1)1.98 (1)2.865 (10)166 (1)
O1—H1···O1C0.90 (1)1.75 (2)2.631 (16)165 (1)
O7—H7···O1A0.96 (1)1.73 (1)2.678 (8)169 (1)
O13—H13···O9i0.99 (1)2.19 (1)3.128 (7)156 (1)
O10—H10···O90.76 (1)2.10 (1)2.581 (5)122 (1)
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC29H36O10·2C2H6OS
Mr700.83
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)9.3677 (10), 21.991 (4), 9.4564 (11)
β (°) 115.827 (9)
V3)1753.5 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.5 × 0.4 × 0.3
Data collection
DiffractometerBruker P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4342, 4103, 3005
Rint0.025
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.136, ?
No. of reflections4100
No. of parameters436
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.26
Absolute structureFlack (1983)
Absolute structure parameter0.08 (15)

Computer programs: Bruker Software, SHELXTL/PC (Sheldrick, 1994), SHELXTL/PC.

Selected geometric parameters (Å, º) top
C1—C141.539 (7)C6—C71.515 (7)
C1—C151.561 (6)C7—C81.567 (7)
C1—C21.566 (6)C8—C91.551 (6)
C2—C31.561 (6)C9—C101.522 (7)
C3—C41.551 (5)C10—C111.509 (6)
C3—C81.579 (5)C11—C121.343 (7)
C4—C201.529 (6)C11—C151.530 (7)
C5—O51.456 (6)C12—C131.524 (7)
C5—C61.523 (7)C13—C141.548 (7)
O5—C201.444 (6)
C14—C1—C15111.1 (4)C6—C7—C8111.4 (4)
C14—C1—C2111.6 (4)C9—C8—C7102.2 (3)
C15—C1—C2111.3 (4)C19—C8—C3113.8 (3)
C3—C2—C1118.8 (3)C9—C8—C3115.8 (3)
C4—C3—C2111.7 (3)C7—C8—C3105.4 (3)
C4—C3—C8110.3 (3)C10—C9—C8122.9 (4)
C2—C3—C8116.0 (3)C11—C10—C9113.2 (3)
C20—C4—C585.8 (3)C12—C11—C10120.5 (4)
C20—C4—C3120.4 (3)C12—C11—C15120.0 (4)
C5—C4—C3120.8 (3)C10—C11—C15119.2 (4)
O5—C5—C6113.7 (4)C11—C12—C13119.5 (4)
O5—C5—C490.8 (4)C12—C13—C14111.5 (4)
C6—C5—C4119.2 (4)C1—C14—C13118.1 (4)
C20—O5—C591.8 (3)C11—C15—C1106.2 (4)
C7—C6—C5113.5 (4)O5—C20—C491.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1B0.900 (6)1.984 (10)2.865 (10)166.3 (6)
O1—H1···O1C0.900 (6)1.754 (16)2.631 (16)164.8 (5)
O7—H7···O1A0.958 (6)1.733 (8)2.678 (8)168.6 (5)
O13—H13···O9i0.993 (8)2.194 (7)3.128 (7)156.1 (8)
O10—H10···O90.755 (7)2.101 (5)2.581 (5)121.9 (5)
Symmetry code: (i) x1, y, z.
 

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