# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'W. Bruce Turnbull'
_publ_contact_author_email       W.B.TURNBULL@LEEDS.AC.UK

_publ_section_title              
;
Stereoselective Glycosylation Using Oxathiane Glycosyl Donors
;
loop_
_publ_author_name
'W. Bruce Turnbull'
'Sophie J. Adshead'
'Martin A. Fascione'
'Colin A. Kilner'
'Andrew Leach'
;
S.A.Stalford
;

# Attachment 'compound_8.CIF'

data_maf209_1
_database_code_depnum_ccdc_archive 'CCDC 733122'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 O10 S'
_chemical_formula_sum            'C21 H26 O10 S'
_chemical_formula_weight         470.48
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.8256(4)
_cell_length_b                   14.5183(12)
_cell_length_c                   27.760(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2347.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7878
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.58

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8278
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   
;
See Sheldrick, G. M. (2002). SADABS. Version
2.03. University of Gottingen, Germany.
;
_exptl_special_details           
;
The crystal temperature was held constant
using an Oxford Cryosystems
Cryostream 600 system.
;
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_monochromator  
;
graphite model mounted in "parallel" mode
;
_diffrn_measurement_device_type  
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_radiation_detector       'ApexII camera'
_diffrn_measurement_method       'rotation images'
_diffrn_detector_area_resol_mean 
;
120 microns
;
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            48554
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.96
_reflns_number_total             5609
_reflns_number_gt                5047
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_cell_refinement       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_reduction        
;
SAINT - Bruker Integration program embedded in
APEX 2 software, Bruker Nonius 2004
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;

_refine_special_details          
;

The structure solved in the orthorhombic spacegroup P21 21 21.

All hydrogen atoms could be located in the Fourier difference map but, in
the final stages of the refinement, they were placed in calculated
positions and refined using a riding model. C-H distances: CH3, 0.98\A;
CH2, 0.99\A; CH, 1.00\A; aromatic, 0.95\A.

All Uiso(H) values were constrained to be 1.2 times (1.5 for methyl) Ueq
of the parent atom.

Despite the reasonable refinement, the terminal oxygen atoms, O62, O72,
O83, of the three acetyl groups displayed elongated displacement
ellipsoids. If this was due to rotational disorder about the O-C axes
(O61-C62, O71-C72, O82-C83), one would expect there to be a corresponding
elongated ellipsoid associated with the methyl C atoms (C63, C73, C84)
of the acetyl groups but that does not occur. Despite that, for the O82,
C83, O83, C84 group, an attempt was made to model a disorder over two
positions using the split positions of O83 as a starting point. This
gave an unsatisfactory result with one of the split methyl C atoms
becoming non-positive definite, despite the application of restraints,
and so the initial model with elongated displacement ellipsoids was retained.

The absolute configuration was established from the x-ray data by
anomalous dispersion effects since the Flack parameter refined to 0.04(6).

C.Kilner 13 November 2006

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.9370P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_number_reflns         5609
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15762(7) 0.29604(3) 0.954605(16) 0.01976(10) Uani 1 1 d . . .
O1 O 0.0989(2) 0.20731(9) 0.98058(5) 0.0243(3) Uani 1 1 d . . .
C2 C 0.1256(3) 0.38875(12) 0.99932(6) 0.0203(3) Uani 1 1 d . . .
H2A H -0.0191 0.3787 1.0173 0.024 Uiso 1 1 calc R . .
H2B H 0.2535 0.3843 1.0227 0.024 Uiso 1 1 calc R . .
C3 C 0.1225(3) 0.48741(12) 0.97805(6) 0.0193(3) Uani 1 1 d . . .
O4 O -0.0514(2) 0.49893(9) 0.94149(4) 0.0205(3) Uani 1 1 d . . .
C5 C -0.0329(3) 0.43242(12) 0.90251(6) 0.0205(4) Uani 1 1 d . . .
H5 H 0.1290 0.4315 0.8906 0.025 Uiso 1 1 calc R . .
C6 C -0.1921(3) 0.46536(13) 0.86138(6) 0.0211(4) Uani 1 1 d . . .
H6 H -0.3370 0.4911 0.8752 0.025 Uiso 1 1 calc R . .
C7 C -0.2499(3) 0.38821(13) 0.82504(7) 0.0231(4) Uani 1 1 d . . .
H7 H -0.1169 0.3760 0.8032 0.028 Uiso 1 1 calc R . .
C8 C -0.3208(3) 0.29965(13) 0.85233(6) 0.0245(4) Uani 1 1 d . . .
H8 H -0.4566 0.3131 0.8732 0.029 Uiso 1 1 calc R . .
O9 O -0.1285(2) 0.27163(9) 0.88236(5) 0.0252(3) Uani 1 1 d . . .
C10 C -0.0967(3) 0.33549(13) 0.92123(6) 0.0201(4) Uani 1 1 d . . .
H10 H -0.2351 0.3378 0.9425 0.024 Uiso 1 1 calc R . .
C31 C 0.0678(3) 0.55537(13) 1.01953(7) 0.0209(4) Uani 1 1 d . . .
C32 C 0.2358(3) 0.56810(14) 1.05559(7) 0.0281(4) Uani 1 1 d . . .
H32 H 0.3781 0.5364 1.0535 0.034 Uiso 1 1 calc R . .
C33 C 0.1930(4) 0.62737(15) 1.09448(8) 0.0335(5) Uani 1 1 d . . .
H33 H 0.3071 0.6357 1.1185 0.040 Uiso 1 1 calc R . .
C34 C -0.0164(4) 0.67435(16) 1.09816(8) 0.0343(5) Uani 1 1 d . . .
H34 H -0.0448 0.7147 1.1245 0.041 Uiso 1 1 calc R . .
C35 C -0.1828(4) 0.66100(15) 1.06255(8) 0.0335(5) Uani 1 1 d . . .
H35 H -0.3255 0.6924 1.0649 0.040 Uiso 1 1 calc R . .
C36 C -0.1420(4) 0.60170(14) 1.02324(7) 0.0276(4) Uani 1 1 d . . .
H36 H -0.2567 0.5932 0.9993 0.033 Uiso 1 1 calc R . .
O37 O 0.3456(2) 0.50347(9) 0.95777(5) 0.0237(3) Uani 1 1 d . . .
C37 C 0.3679(4) 0.59543(14) 0.93681(7) 0.0294(4) Uani 1 1 d . . .
H37A H 0.2711 0.5999 0.9080 0.044 Uiso 1 1 calc R . .
H37B H 0.5284 0.6064 0.9279 0.044 Uiso 1 1 calc R . .
H37C H 0.3191 0.6416 0.9604 0.044 Uiso 1 1 calc R . .
O61 O -0.0639(2) 0.53856(10) 0.83671(5) 0.0270(3) Uani 1 1 d . . .
O62 O -0.3769(4) 0.63236(13) 0.83227(7) 0.0572(6) Uani 1 1 d . . .
C62 C -0.1720(5) 0.62011(14) 0.82660(7) 0.0340(5) Uani 1 1 d . . .
C63 C -0.0011(5) 0.68972(17) 0.80783(9) 0.0463(6) Uani 1 1 d . . .
H63A H -0.0459 0.7091 0.7753 0.069 Uiso 1 1 calc R . .
H63B H 0.1520 0.6618 0.8068 0.069 Uiso 1 1 calc R . .
H63C H 0.0015 0.7434 0.8292 0.069 Uiso 1 1 calc R . .
O71 O -0.4485(2) 0.41968(11) 0.79774(5) 0.0290(3) Uani 1 1 d . . .
O72 O -0.2650(4) 0.4000(2) 0.72633(7) 0.0734(7) Uani 1 1 d . . .
C72 C -0.4333(4) 0.42515(16) 0.74898(8) 0.0340(5) Uani 1 1 d . . .
C73 C -0.6564(5) 0.46119(19) 0.72810(9) 0.0465(6) Uani 1 1 d . . .
H73A H -0.6341 0.4764 0.6940 0.070 Uiso 1 1 calc R . .
H73B H -0.7037 0.5165 0.7457 0.070 Uiso 1 1 calc R . .
H73C H -0.7756 0.4139 0.7311 0.070 Uiso 1 1 calc R . .
C81 C -0.3763(4) 0.21858(14) 0.81903(7) 0.0322(5) Uani 1 1 d . . .
H81A H -0.4742 0.2394 0.7920 0.039 Uiso 1 1 calc R . .
H81B H -0.2331 0.1924 0.8056 0.039 Uiso 1 1 calc R . .
O82 O -0.4968(3) 0.14919(11) 0.84760(6) 0.0382(4) Uani 1 1 d . . .
O83 O -0.8019(3) 0.1567(2) 0.79891(8) 0.0929(10) Uani 1 1 d . . .
C83 C -0.7136(4) 0.12735(17) 0.83443(8) 0.0360(5) Uani 1 1 d . . .
C84 C -0.8238(5) 0.06157(17) 0.86971(9) 0.0424(5) Uani 1 1 d . . .
H84A H -0.9858 0.0531 0.8613 0.064 Uiso 1 1 calc R . .
H84B H -0.8125 0.0869 0.9023 0.064 Uiso 1 1 calc R . .
H84C H -0.7446 0.0021 0.8684 0.064 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.02010(19) 0.0187(2) 0.0205(2) 0.00089(17) -0.00003(17) 0.00147(17)
O1 0.0265(6) 0.0187(6) 0.0277(7) 0.0052(6) -0.0029(5) 0.0001(5)
C2 0.0221(8) 0.0204(8) 0.0183(8) 0.0001(7) -0.0013(6) 0.0009(7)
C3 0.0189(8) 0.0208(8) 0.0181(8) 0.0005(7) -0.0006(7) 0.0012(7)
O4 0.0210(6) 0.0194(6) 0.0212(6) -0.0011(5) -0.0021(5) 0.0025(5)
C5 0.0212(8) 0.0211(9) 0.0191(8) -0.0014(7) 0.0001(7) 0.0013(7)
C6 0.0223(9) 0.0221(9) 0.0191(8) 0.0018(7) -0.0010(7) 0.0004(7)
C7 0.0227(8) 0.0263(9) 0.0203(9) -0.0015(7) -0.0013(7) 0.0021(8)
C8 0.0256(9) 0.0261(9) 0.0218(8) -0.0009(8) -0.0034(7) -0.0007(8)
O9 0.0303(7) 0.0229(6) 0.0224(6) -0.0026(5) -0.0062(6) 0.0026(5)
C10 0.0230(9) 0.0184(8) 0.0190(8) -0.0001(7) -0.0027(6) 0.0010(7)
C31 0.0233(8) 0.0190(9) 0.0206(8) 0.0009(7) 0.0004(7) -0.0028(7)
C32 0.0266(9) 0.0321(10) 0.0255(10) -0.0028(8) -0.0028(8) 0.0005(8)
C33 0.0364(11) 0.0367(11) 0.0273(10) -0.0074(9) -0.0036(8) -0.0065(9)
C34 0.0416(12) 0.0292(11) 0.0320(11) -0.0090(9) 0.0070(9) -0.0066(9)
C35 0.0293(10) 0.0290(10) 0.0423(12) -0.0075(9) 0.0060(9) 0.0022(9)
C36 0.0254(9) 0.0271(10) 0.0303(10) -0.0039(8) -0.0027(8) 0.0002(8)
O37 0.0203(6) 0.0255(6) 0.0253(6) 0.0019(6) 0.0030(6) -0.0002(5)
C37 0.0295(10) 0.0278(10) 0.0310(10) 0.0084(8) 0.0032(8) -0.0037(8)
O61 0.0309(7) 0.0239(7) 0.0264(7) 0.0060(6) -0.0026(6) -0.0009(6)
O62 0.0660(13) 0.0473(11) 0.0583(12) 0.0232(9) 0.0242(10) 0.0288(10)
C62 0.0556(14) 0.0269(10) 0.0194(9) 0.0038(8) 0.0032(9) 0.0069(11)
C63 0.0755(18) 0.0290(12) 0.0344(12) 0.0096(9) -0.0069(12) -0.0108(12)
O71 0.0278(7) 0.0374(8) 0.0218(6) -0.0013(6) -0.0057(6) 0.0065(6)
O72 0.0552(12) 0.135(2) 0.0297(9) 0.0187(12) 0.0054(9) 0.0195(14)
C72 0.0399(12) 0.0375(12) 0.0246(10) 0.0096(9) -0.0048(9) -0.0073(10)
C73 0.0519(14) 0.0516(15) 0.0361(12) 0.0096(11) -0.0188(12) 0.0003(13)
C81 0.0411(12) 0.0276(10) 0.0280(10) -0.0002(8) -0.0090(9) -0.0057(9)
O82 0.0473(9) 0.0281(8) 0.0394(9) 0.0079(7) -0.0185(7) -0.0095(7)
O83 0.0356(10) 0.186(3) 0.0574(13) 0.0612(17) -0.0137(9) -0.0212(14)
C83 0.0338(11) 0.0483(13) 0.0259(10) -0.0045(10) 0.0006(8) 0.0022(10)
C84 0.0475(13) 0.0402(13) 0.0396(12) -0.0032(10) 0.0005(11) -0.0061(11)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.5154(14) . ?
S1 C10 1.8390(18) . ?
S1 C2 1.8405(18) . ?
C2 C3 1.549(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O37 1.435(2) . ?
C3 O4 1.444(2) . ?
C3 C31 1.549(2) . ?
O4 C5 1.454(2) . ?
C5 C10 1.545(3) . ?
C5 C6 1.547(2) . ?
C5 H5 1.0000 . ?
C6 O61 1.468(2) . ?
C6 C7 1.545(3) . ?
C6 H6 1.0000 . ?
C7 O71 1.457(2) . ?
C7 C8 1.548(3) . ?
C7 H7 1.0000 . ?
C8 O9 1.454(2) . ?
C8 C81 1.531(3) . ?
C8 H8 1.0000 . ?
O9 C10 1.435(2) . ?
C10 H10 1.0000 . ?
C31 C36 1.399(3) . ?
C31 C32 1.412(3) . ?
C32 C33 1.403(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.401(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.398(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.410(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
O37 C37 1.462(2) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
O61 C62 1.370(3) . ?
O62 C62 1.217(3) . ?
C62 C63 1.512(3) . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
O71 C72 1.359(3) . ?
O72 C72 1.220(3) . ?
C72 C73 1.516(3) . ?
C73 H73A 0.9800 . ?
C73 H73B 0.9800 . ?
C73 H73C 0.9800 . ?
C81 O82 1.462(3) . ?
C81 H81A 0.9900 . ?
C81 H81B 0.9900 . ?
O82 C83 1.353(3) . ?
O83 C83 1.191(3) . ?
C83 C84 1.511(3) . ?
C84 H84A 0.9800 . ?
C84 H84B 0.9800 . ?
C84 H84C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C10 108.83(8) . . ?
O1 S1 C2 106.13(8) . . ?
C10 S1 C2 91.74(8) . . ?
C3 C2 S1 114.85(12) . . ?
C3 C2 H2A 108.6 . . ?
S1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
S1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.5 . . ?
O37 C3 O4 109.93(13) . . ?
O37 C3 C2 106.82(14) . . ?
O4 C3 C2 112.52(14) . . ?
O37 C3 C31 111.98(14) . . ?
O4 C3 C31 107.71(14) . . ?
C2 C3 C31 107.93(14) . . ?
C3 O4 C5 113.20(13) . . ?
O4 C5 C10 109.67(14) . . ?
O4 C5 C6 107.43(14) . . ?
C10 C5 C6 112.68(15) . . ?
O4 C5 H5 109.0 . . ?
C10 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
O61 C6 C7 109.35(14) . . ?
O61 C6 C5 105.25(14) . . ?
C7 C6 C5 112.88(15) . . ?
O61 C6 H6 109.8 . . ?
C7 C6 H6 109.8 . . ?
C5 C6 H6 109.8 . . ?
O71 C7 C6 106.59(15) . . ?
O71 C7 C8 107.66(15) . . ?
C6 C7 C8 109.92(15) . . ?
O71 C7 H7 110.8 . . ?
C6 C7 H7 110.8 . . ?
C8 C7 H7 110.8 . . ?
O9 C8 C81 107.08(15) . . ?
O9 C8 C7 107.90(15) . . ?
C81 C8 C7 113.53(15) . . ?
O9 C8 H8 109.4 . . ?
C81 C8 H8 109.4 . . ?
C7 C8 H8 109.4 . . ?
C10 O9 C8 110.46(13) . . ?
O9 C10 C5 111.51(14) . . ?
O9 C10 S1 106.35(12) . . ?
C5 C10 S1 105.02(12) . . ?
O9 C10 H10 111.2 . . ?
C5 C10 H10 111.2 . . ?
S1 C10 H10 111.2 . . ?
C36 C31 C32 119.36(17) . . ?
C36 C31 C3 122.72(16) . . ?
C32 C31 C3 117.89(16) . . ?
C33 C32 C31 120.20(19) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C34 C33 C32 120.6(2) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 119.0(2) . . ?
C35 C34 H34 120.5 . . ?
C33 C34 H34 120.5 . . ?
C34 C35 C36 121.0(2) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C31 C36 C35 119.86(19) . . ?
C31 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C3 O37 C37 112.64(14) . . ?
O37 C37 H37A 109.5 . . ?
O37 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O37 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C62 O61 C6 119.16(16) . . ?
O62 C62 O61 123.4(2) . . ?
O62 C62 C63 126.4(2) . . ?
O61 C62 C63 110.2(2) . . ?
C62 C63 H63A 109.5 . . ?
C62 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C62 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C72 O71 C7 118.98(16) . . ?
O72 C72 O71 123.2(2) . . ?
O72 C72 C73 126.5(2) . . ?
O71 C72 C73 110.2(2) . . ?
C72 C73 H73A 109.5 . . ?
C72 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
C72 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
O82 C81 C8 107.68(16) . . ?
O82 C81 H81A 110.2 . . ?
C8 C81 H81A 110.2 . . ?
O82 C81 H81B 110.2 . . ?
C8 C81 H81B 110.2 . . ?
H81A C81 H81B 108.5 . . ?
C83 O82 C81 117.61(17) . . ?
O83 C83 O82 122.9(2) . . ?
O83 C83 C84 125.4(2) . . ?
O82 C83 C84 111.7(2) . . ?
C83 C84 H84A 109.5 . . ?
C83 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
C83 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C2 C3 -166.58(12) . . . . ?
C10 S1 C2 C3 -56.40(14) . . . . ?
S1 C2 C3 O37 -65.57(16) . . . . ?
S1 C2 C3 O4 55.15(17) . . . . ?
S1 C2 C3 C31 173.85(12) . . . . ?
O37 C3 O4 C5 63.51(18) . . . . ?
C2 C3 O4 C5 -55.41(18) . . . . ?
C31 C3 O4 C5 -174.24(14) . . . . ?
C3 O4 C5 C10 69.32(18) . . . . ?
C3 O4 C5 C6 -167.90(14) . . . . ?
O4 C5 C6 O61 79.05(16) . . . . ?
C10 C5 C6 O61 -160.04(14) . . . . ?
O4 C5 C6 C7 -161.75(15) . . . . ?
C10 C5 C6 C7 -40.8(2) . . . . ?
O61 C6 C7 O71 -79.80(17) . . . . ?
C5 C6 C7 O71 163.41(15) . . . . ?
O61 C6 C7 C8 163.80(14) . . . . ?
C5 C6 C7 C8 47.0(2) . . . . ?
O71 C7 C8 O9 -175.95(14) . . . . ?
C6 C7 C8 O9 -60.23(19) . . . . ?
O71 C7 C8 C81 65.5(2) . . . . ?
C6 C7 C8 C81 -178.74(16) . . . . ?
C81 C8 O9 C10 -167.82(15) . . . . ?
C7 C8 O9 C10 69.63(17) . . . . ?
C8 O9 C10 C5 -63.40(19) . . . . ?
C8 O9 C10 S1 -177.36(12) . . . . ?
O4 C5 C10 O9 167.64(13) . . . . ?
C6 C5 C10 O9 48.0(2) . . . . ?
O4 C5 C10 S1 -77.58(15) . . . . ?
C6 C5 C10 S1 162.80(12) . . . . ?
O1 S1 C10 O9 -69.94(13) . . . . ?
C2 S1 C10 O9 -177.65(12) . . . . ?
O1 S1 C10 C5 171.74(11) . . . . ?
C2 S1 C10 C5 64.04(12) . . . . ?
O37 C3 C31 C36 133.75(18) . . . . ?
O4 C3 C31 C36 12.8(2) . . . . ?
C2 C3 C31 C36 -109.0(2) . . . . ?
O37 C3 C31 C32 -48.3(2) . . . . ?
O4 C3 C31 C32 -169.25(16) . . . . ?
C2 C3 C31 C32 69.0(2) . . . . ?
C36 C31 C32 C33 -0.6(3) . . . . ?
C3 C31 C32 C33 -178.66(18) . . . . ?
C31 C32 C33 C34 0.2(3) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C33 C34 C35 C36 -0.3(3) . . . . ?
C32 C31 C36 C35 0.5(3) . . . . ?
C3 C31 C36 C35 178.49(18) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
O4 C3 O37 C37 58.43(18) . . . . ?
C2 C3 O37 C37 -179.21(14) . . . . ?
C31 C3 O37 C37 -61.25(18) . . . . ?
C7 C6 O61 C62 106.29(18) . . . . ?
C5 C6 O61 C62 -132.18(17) . . . . ?
C6 O61 C62 O62 -8.2(3) . . . . ?
C6 O61 C62 C63 171.97(16) . . . . ?
C6 C7 O71 C72 122.92(19) . . . . ?
C8 C7 O71 C72 -119.18(19) . . . . ?
C7 O71 C72 O72 4.3(4) . . . . ?
C7 O71 C72 C73 -178.79(18) . . . . ?
O9 C8 C81 O82 75.83(19) . . . . ?
C7 C8 C81 O82 -165.19(16) . . . . ?
C8 C81 O82 C83 118.3(2) . . . . ?
C81 O82 C83 O83 5.9(4) . . . . ?
C81 O82 C83 C84 -174.77(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.96
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.048