# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Peter H. Seeberger'
'Siwarutt Boonyarattanakalin'
'Bastien Castagner'
'Xinyu Liu.'
'Reiko Wada'

_publ_contact_author_name        'Peter H. Seeberger'
_publ_contact_author_address     
;
Department of Chemistry
Laboratorium fur Organische Chemie
ETH Honnggerberg / HCI F 315
Wolfgang-Pauli-Strasse 10
Zurich
CH 8093 Zurich
SWITZERLAND
;

_publ_contact_author_email       SEEBERGER@ORG.CHEM.ETHZ.CH

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Automated Synthesis of Lipomannan Backbone ?(1-6)
Oligomannoside via Glycosyl Phosphate: Glycosyl Tricyclic Orthoester
Revisited
;

data_xliu1_seeber_06
_database_code_depnum_ccdc_archive 'CCDC 681095'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H26 O6'
_chemical_absolute_configuration syn
_chemical_formula_sum            'C27 H26 O6'
_chemical_formula_weight         446.48

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   9.9274(6)
_cell_length_b                   9.4363(7)
_cell_length_c                   12.4041(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.452(3)
_cell_angle_gamma                90.00
_cell_volume                     1108.50(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8364
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      25.98

_exptl_crystal_description       'Cut fragment'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            3686
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.98
_reflns_number_total             2248
_reflns_number_gt                2019
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Kappa CCD'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo + Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et Al., 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
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^)+(0.0496P)^2^+0.2717P] 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    riding
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef       0.095(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2313(3) 0.5402(3) 0.7217(2) 0.0314(6) Uani 1 d . . .
O2 O 0.34137(19) 0.5894(2) 0.68228(16) 0.0339(5) Uani 1 d . . .
C3 C 0.4329(3) 0.6740(3) 0.7688(2) 0.0324(6) Uani 1 d . . .
H3A H 0.5329 0.6585 0.7697 0.028(7) Uiso 1 calc R . .
C4 C 0.4121(3) 0.6156(3) 0.8785(2) 0.0318(6) Uani 1 d . . .
H4A H 0.4969 0.5595 0.9210 0.045(9) Uiso 1 calc R . .
O5 O 0.29107(19) 0.5238(2) 0.84074(16) 0.0335(5) Uani 1 d . . .
O6 O 0.11819(19) 0.6360(2) 0.69912(17) 0.0352(5) Uani 1 d . . .
C7 C 0.1434(3) 0.7815(3) 0.6777(2) 0.0352(6) Uani 1 d . . .
H7A H 0.0557 0.8357 0.6702 0.029(7) Uiso 1 calc R . .
H7B H 0.1633 0.7869 0.6042 0.043(9) Uiso 1 calc R . .
C8 C 0.2637(3) 0.8539(3) 0.7665(2) 0.0320(6) Uani 1 d . . .
H8A H 0.2505 0.9581 0.7530 0.041(7) Uiso 1 calc R . .
O9 O 0.3996(2) 0.8186(2) 0.75255(17) 0.0346(5) Uani 1 d . . .
C10 C 0.2630(3) 0.8274(3) 0.8885(2) 0.0312(6) Uani 1 d . . .
H10A H 0.1735 0.7777 0.8872 0.037(8) Uiso 1 calc R . .
C11 C 0.3876(3) 0.7372(3) 0.9521(2) 0.0310(6) Uani 1 d . . .
H11A H 0.4739 0.7981 0.9745 0.050(7) Uiso 1 calc R . .
O12 O 0.35849(19) 0.6901(2) 1.05156(16) 0.0353(5) Uani 1 d . . .
C13 C 0.4779(3) 0.6660(4) 1.1479(2) 0.0400(7) Uani 1 d . . .
H13A H 0.5583 0.7251 1.1432 0.044(9) Uiso 1 calc R . .
H13B H 0.5066 0.5652 1.1509 0.061(12) Uiso 1 calc R . .
C14 C 0.4378(3) 0.7037(3) 1.2521(2) 0.0345(6) Uani 1 d . . .
C15 C 0.3803(3) 0.8347(4) 1.2599(2) 0.0379(7) Uani 1 d . . .
H15A H 0.3604 0.8977 1.1973 0.045(9) Uiso 1 calc R . .
C16 C 0.3509(3) 0.8759(4) 1.3583(3) 0.0445(7) Uani 1 d . . .
H16A H 0.3114 0.9666 1.3627 0.050(10) Uiso 1 calc R . .
C17 C 0.3797(3) 0.7843(4) 1.4499(3) 0.0470(8) Uani 1 d . . .
H17A H 0.3628 0.8131 1.5181 0.082(14) Uiso 1 calc R . .
C18 C 0.4326(3) 0.6517(4) 1.4414(3) 0.0447(7) Uani 1 d . . .
H18A H 0.4490 0.5873 1.5029 0.055(10) Uiso 1 calc R . .
C19 C 0.4625(3) 0.6108(4) 1.3425(2) 0.0389(7) Uani 1 d . . .
H19A H 0.4998 0.5192 1.3373 0.048(10) Uiso 1 calc R . .
O20 O 0.27363(19) 0.9561(2) 0.95118(17) 0.0356(5) Uani 1 d . . .
C21 C 0.1415(3) 1.0247(5) 0.9366(3) 0.0570(10) Uani 1 d . . .
H21A H 0.0705 0.9549 0.9443 0.095(17) Uiso 1 calc R . .
H21B H 0.1077 1.0671 0.8602 0.081(15) Uiso 1 calc R . .
C22 C 0.1601(3) 1.1378(3) 1.0243(3) 0.0380(7) Uani 1 d . . .
C23 C 0.2034(3) 1.2723(4) 1.0072(3) 0.0456(8) Uani 1 d . . .
H23A H 0.2196 1.2945 0.9374 0.090(16) Uiso 1 calc R . .
C24 C 0.2236(4) 1.3745(4) 1.0887(4) 0.0568(10) Uani 1 d . . .
H24A H 0.2525 1.4671 1.0750 0.073(13) Uiso 1 calc R . .
C25 C 0.2017(3) 1.3424(4) 1.1915(3) 0.0567(10) Uani 1 d . . .
H25A H 0.2175 1.4122 1.2492 0.068(12) Uiso 1 calc R . .
C26 C 0.1572(4) 1.2099(5) 1.2089(3) 0.0533(9) Uani 1 d . . .
H26A H 0.1411 1.1879 1.2788 0.080(14) Uiso 1 calc R . .
C27 C 0.1356(3) 1.1082(4) 1.1265(3) 0.0459(8) Uani 1 d . . .
H27A H 0.1035 1.0167 1.1394 0.047(9) Uiso 1 calc R . .
C28 C 0.1732(3) 0.3999(3) 0.6700(2) 0.0332(6) Uani 1 d . . .
C29 C 0.2351(3) 0.3260(4) 0.6010(3) 0.0409(7) Uani 1 d . . .
H29A H 0.3166 0.3627 0.5857 0.066(12) Uiso 1 calc R . .
C30 C 0.1774(4) 0.1975(4) 0.5540(3) 0.0507(9) Uani 1 d . . .
H30A H 0.2202 0.1467 0.5068 0.060(11) Uiso 1 calc R . .
C31 C 0.0589(4) 0.1429(4) 0.5750(3) 0.0475(8) Uani 1 d . . .
H31A H 0.0202 0.0552 0.5425 0.067(12) Uiso 1 calc R . .
C32 C -0.0030(4) 0.2168(4) 0.6438(3) 0.0476(8) Uani 1 d . . .
H32A H -0.0846 0.1799 0.6588 0.062(11) Uiso 1 calc R . .
C33 C 0.0539(3) 0.3448(4) 0.6910(3) 0.0427(7) Uani 1 d . . .
H33A H 0.0107 0.3953 0.7381 0.058(11) Uiso 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
C1 0.0323(13) 0.0328(15) 0.0283(13) 0.0029(12) 0.0077(10) 0.0013(12)
O2 0.0356(9) 0.0374(11) 0.0309(9) -0.0013(8) 0.0132(8) -0.0036(8)
C3 0.0322(12) 0.0337(15) 0.0335(14) -0.0018(12) 0.0130(11) -0.0004(12)
C4 0.0275(12) 0.0332(15) 0.0334(13) 0.0014(12) 0.0070(10) -0.0012(12)
O5 0.0382(10) 0.0335(10) 0.0277(9) -0.0012(8) 0.0083(7) -0.0071(9)
O6 0.0329(9) 0.0296(10) 0.0419(11) -0.0015(9) 0.0095(8) -0.0006(8)
C7 0.0397(15) 0.0325(15) 0.0315(14) 0.0030(12) 0.0076(11) -0.0018(12)
C8 0.0350(13) 0.0307(14) 0.0308(13) 0.0010(12) 0.0106(11) 0.0012(11)
O9 0.0365(9) 0.0332(11) 0.0366(10) 0.0019(9) 0.0148(8) -0.0028(9)
C10 0.0321(13) 0.0316(14) 0.0290(13) -0.0036(11) 0.0077(10) -0.0041(11)
C11 0.0326(13) 0.0355(15) 0.0256(12) 0.0012(12) 0.0098(10) -0.0038(12)
O12 0.0372(10) 0.0412(12) 0.0265(9) 0.0029(8) 0.0079(8) -0.0033(9)
C13 0.0420(14) 0.0474(18) 0.0279(14) 0.0028(13) 0.0064(11) 0.0101(14)
C14 0.0317(13) 0.0412(16) 0.0291(13) -0.0056(12) 0.0069(11) -0.0024(12)
C15 0.0394(14) 0.0401(17) 0.0336(14) 0.0002(13) 0.0101(12) 0.0002(13)
C16 0.0465(16) 0.0429(18) 0.0449(17) -0.0098(15) 0.0152(13) 0.0047(15)
C17 0.0457(16) 0.061(2) 0.0378(16) -0.0069(16) 0.0170(13) -0.0017(16)
C18 0.0500(16) 0.0525(19) 0.0333(15) 0.0049(15) 0.0151(13) -0.0004(16)
C19 0.0417(14) 0.0390(17) 0.0349(14) -0.0004(13) 0.0099(11) -0.0001(14)
O20 0.0318(9) 0.0351(11) 0.0395(10) -0.0051(9) 0.0100(8) 0.0005(9)
C21 0.0383(16) 0.061(2) 0.062(2) -0.019(2) 0.0001(15) 0.0129(17)
C22 0.0286(13) 0.0411(17) 0.0434(16) -0.0017(14) 0.0094(11) 0.0055(12)
C23 0.0388(16) 0.0496(19) 0.0527(19) 0.0122(16) 0.0200(14) 0.0035(14)
C24 0.0428(17) 0.0381(19) 0.088(3) 0.0039(19) 0.0176(18) -0.0034(15)
C25 0.0417(17) 0.057(2) 0.068(2) -0.025(2) 0.0110(16) 0.0099(16)
C26 0.0461(17) 0.074(3) 0.0448(18) 0.0006(18) 0.0203(15) 0.0135(19)
C27 0.0414(15) 0.0400(17) 0.061(2) 0.0104(16) 0.0225(14) 0.0045(14)
C28 0.0352(13) 0.0289(14) 0.0312(13) 0.0024(12) 0.0032(11) 0.0001(12)
C29 0.0427(15) 0.0408(17) 0.0368(15) -0.0049(14) 0.0083(12) 0.0032(14)
C30 0.0552(18) 0.0444(19) 0.0467(18) -0.0105(16) 0.0062(15) 0.0098(16)
C31 0.0563(18) 0.0309(16) 0.0398(16) -0.0014(14) -0.0091(14) 0.0021(15)
C32 0.0483(17) 0.0354(17) 0.0535(19) 0.0036(15) 0.0067(15) -0.0088(14)
C33 0.0437(16) 0.0403(17) 0.0427(16) 0.0015(14) 0.0108(13) -0.0034(14)

_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
C1 O2 1.403(3) . ?
C1 O6 1.403(3) . ?
C1 O5 1.425(3) . ?
C1 C28 1.509(4) . ?
O2 C3 1.425(3) . ?
C3 O9 1.404(4) . ?
C3 C4 1.538(4) . ?
C4 O5 1.441(3) . ?
C4 C11 1.531(4) . ?
O6 C7 1.435(4) . ?
C7 C8 1.521(4) . ?
C8 O9 1.450(3) . ?
C8 C10 1.536(4) . ?
C10 O20 1.429(3) . ?
C10 C11 1.514(4) . ?
C11 O12 1.419(3) . ?
O12 C13 1.427(3) . ?
C13 C14 1.505(4) . ?
C14 C15 1.376(4) . ?
C14 C19 1.386(4) . ?
C15 C16 1.393(4) . ?
C16 C17 1.389(5) . ?
C17 C18 1.374(5) . ?
C18 C19 1.400(4) . ?
O20 C21 1.425(4) . ?
C21 C22 1.496(5) . ?
C22 C23 1.377(5) . ?
C22 C27 1.389(5) . ?
C23 C24 1.368(6) . ?
C24 C25 1.391(6) . ?
C25 C26 1.365(6) . ?
C26 C27 1.371(5) . ?
C28 C33 1.388(4) . ?
C28 C29 1.383(4) . ?
C29 C30 1.392(5) . ?
C30 C31 1.379(5) . ?
C31 C32 1.380(5) . ?
C32 C33 1.386(5) . ?

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
O2 C1 O6 112.2(2) . . ?
O2 C1 O5 105.8(2) . . ?
O6 C1 O5 109.7(2) . . ?
O2 C1 C28 112.4(2) . . ?
O6 C1 C28 107.4(2) . . ?
O5 C1 C28 109.4(2) . . ?
C1 O2 C3 108.1(2) . . ?
O9 C3 O2 111.5(2) . . ?
O9 C3 C4 112.8(2) . . ?
O2 C3 C4 104.0(2) . . ?
O5 C4 C11 112.2(2) . . ?
O5 C4 C3 104.3(2) . . ?
C11 C4 C3 110.3(2) . . ?
C1 O5 C4 108.6(2) . . ?
C1 O6 C7 118.7(2) . . ?
O6 C7 C8 116.0(2) . . ?
O9 C8 C7 111.5(2) . . ?
O9 C8 C10 111.0(2) . . ?
C7 C8 C10 113.9(2) . . ?
C3 O9 C8 113.2(2) . . ?
O20 C10 C11 106.2(2) . . ?
O20 C10 C8 112.1(2) . . ?
C11 C10 C8 111.2(2) . . ?
O12 C11 C10 106.4(2) . . ?
O12 C11 C4 113.2(2) . . ?
C10 C11 C4 111.2(2) . . ?
C11 O12 C13 116.3(2) . . ?
O12 C13 C14 108.3(2) . . ?
C15 C14 C19 119.2(3) . . ?
C15 C14 C13 119.7(3) . . ?
C19 C14 C13 121.1(3) . . ?
C14 C15 C16 120.8(3) . . ?
C15 C16 C17 119.9(3) . . ?
C18 C17 C16 119.6(3) . . ?
C17 C18 C19 120.3(3) . . ?
C14 C19 C18 120.1(3) . . ?
C10 O20 C21 113.7(2) . . ?
O20 C21 C22 108.9(2) . . ?
C23 C22 C27 118.3(3) . . ?
C23 C22 C21 121.4(3) . . ?
C27 C22 C21 120.2(3) . . ?
C24 C23 C22 121.3(3) . . ?
C23 C24 C25 119.7(3) . . ?
C26 C25 C24 119.5(3) . . ?
C25 C26 C27 120.6(3) . . ?
C26 C27 C22 120.5(3) . . ?
C33 C28 C29 119.3(3) . . ?
C33 C28 C1 119.2(3) . . ?
C29 C28 C1 121.4(3) . . ?
C30 C29 C28 119.7(3) . . ?
C29 C30 C31 120.9(3) . . ?
C32 C31 C30 119.4(3) . . ?
C31 C32 C33 120.0(3) . . ?
C28 C33 C32 120.6(3) . . ?

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
O6 C1 O2 C3 87.7(3) . . . . ?
O5 C1 O2 C3 -31.9(3) . . . . ?
C28 C1 O2 C3 -151.2(2) . . . . ?
C1 O2 C3 O9 -95.4(3) . . . . ?
C1 O2 C3 C4 26.4(3) . . . . ?
O9 C3 C4 O5 109.9(2) . . . . ?
O2 C3 C4 O5 -11.0(3) . . . . ?
O9 C3 C4 C11 -10.8(3) . . . . ?
O2 C3 C4 C11 -131.7(2) . . . . ?
O2 C1 O5 C4 24.1(3) . . . . ?
O6 C1 O5 C4 -97.1(2) . . . . ?
C28 C1 O5 C4 145.3(2) . . . . ?
C11 C4 O5 C1 111.7(2) . . . . ?
C3 C4 O5 C1 -7.7(3) . . . . ?
O2 C1 O6 C7 -20.8(3) . . . . ?
O5 C1 O6 C7 96.5(3) . . . . ?
C28 C1 O6 C7 -144.7(2) . . . . ?
C1 O6 C7 C8 -53.2(3) . . . . ?
O6 C7 C8 O9 80.5(3) . . . . ?
O6 C7 C8 C10 -46.2(3) . . . . ?
O2 C3 O9 C8 67.1(3) . . . . ?
C4 C3 O9 C8 -49.4(3) . . . . ?
C7 C8 O9 C3 -63.9(3) . . . . ?
C10 C8 O9 C3 64.4(3) . . . . ?
O9 C8 C10 O20 103.7(3) . . . . ?
C7 C8 C10 O20 -129.3(3) . . . . ?
O9 C8 C10 C11 -14.9(3) . . . . ?
C7 C8 C10 C11 112.0(3) . . . . ?
O20 C10 C11 O12 72.0(3) . . . . ?
C8 C10 C11 O12 -165.8(2) . . . . ?
O20 C10 C11 C4 -164.3(2) . . . . ?
C8 C10 C11 C4 -42.1(3) . . . . ?
O5 C4 C11 O12 60.3(3) . . . . ?
C3 C4 C11 O12 176.2(2) . . . . ?
O5 C4 C11 C10 -59.4(3) . . . . ?
C3 C4 C11 C10 56.5(3) . . . . ?
C10 C11 O12 C13 -150.1(2) . . . . ?
C4 C11 O12 C13 87.5(3) . . . . ?
C11 O12 C13 C14 146.3(3) . . . . ?
O12 C13 C14 C15 -52.9(4) . . . . ?
O12 C13 C14 C19 129.5(3) . . . . ?
C19 C14 C15 C16 1.9(4) . . . . ?
C13 C14 C15 C16 -175.7(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 -2.1(5) . . . . ?
C16 C17 C18 C19 2.4(5) . . . . ?
C15 C14 C19 C18 -1.6(4) . . . . ?
C13 C14 C19 C18 175.9(3) . . . . ?
C17 C18 C19 C14 -0.5(4) . . . . ?
C11 C10 O20 C21 -153.5(3) . . . . ?
C8 C10 O20 C21 84.9(3) . . . . ?
C10 O20 C21 C22 167.4(3) . . . . ?
O20 C21 C22 C23 86.6(4) . . . . ?
O20 C21 C22 C27 -92.6(4) . . . . ?
C27 C22 C23 C24 0.7(5) . . . . ?
C21 C22 C23 C24 -178.4(3) . . . . ?
C22 C23 C24 C25 0.7(5) . . . . ?
C23 C24 C25 C26 -1.4(5) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C25 C26 C27 C22 0.8(5) . . . . ?
C23 C22 C27 C26 -1.5(4) . . . . ?
C21 C22 C27 C26 177.7(3) . . . . ?
O2 C1 C28 C33 -173.0(3) . . . . ?
O6 C1 C28 C33 -49.1(3) . . . . ?
O5 C1 C28 C33 69.9(3) . . . . ?
O2 C1 C28 C29 6.1(4) . . . . ?
O6 C1 C28 C29 129.9(3) . . . . ?
O5 C1 C28 C29 -111.1(3) . . . . ?
C33 C28 C29 C30 -0.3(4) . . . . ?
C1 C28 C29 C30 -179.3(3) . . . . ?
C28 C29 C30 C31 0.2(5) . . . . ?
C29 C30 C31 C32 -0.1(5) . . . . ?
C30 C31 C32 C33 0.1(5) . . . . ?
C29 C28 C33 C32 0.2(4) . . . . ?
C1 C28 C33 C32 179.3(3) . . . . ?
C31 C32 C33 C28 -0.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035