# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TE-3
_database_code_depnum_ccdc_archive 'CCDC 1546638'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H42 O9'
_chemical_formula_weight         534.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.27418(11)
_cell_length_b                   12.53092(12)
_cell_length_c                   10.87663(16)
_cell_angle_alpha                90.0
_cell_angle_beta                 107.8950(10)
_cell_angle_gamma                90.0
_cell_volume                     1332.57(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    9344
_cell_measurement_theta_min      4.2490
_cell_measurement_theta_max      73.4000

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.806
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_reflns_number            12315
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.5271
_diffrn_reflns_theta_max         73.5276
_diffrn_reflns_theta_full        66.9682
_diffrn_measured_fraction_theta_max 0.9600
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5169
_reflns_number_gt                5047
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.969

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0803P)²+0.9278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0018(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(10)
_chemical_absolute_configuration re
_refine_ls_number_reflns         5169
_refine_ls_number_parameters     353
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6926(3) 0.5773(2) 0.1970(3) 0.0277(6) Uani 1 1 d . . . . .
O2 O 0.0853(2) 0.4772(2) 0.5011(2) 0.0229(5) Uani 1 1 d . . . . .
H2 H 0.029825 0.483294 0.428901 0.034 Uiso 1 1 calc R U . . .
O3 O 0.1738(3) 0.4681(2) 0.7889(3) 0.0323(6) Uani 1 1 d . . . . .
O4 O 0.3653(4) 0.3967(3) 0.9179(3) 0.0550(10) Uani 1 1 d . . . . .
O5 O -0.1557(3) 0.7158(2) 0.8001(3) 0.0320(6) Uani 1 1 d . . . . .
O6 O -0.3675(3) 0.6555(3) 0.7498(4) 0.0552(10) Uani 1 1 d . . . . .
O7 O 0.8714(3) 0.4642(3) 0.2653(3) 0.0387(7) Uani 1 1 d . . . . .
O8 O 0.9178(4) 0.4809(4) 0.0321(4) 0.0655(12) Uani 1 1 d . . . . .
H8 H 0.978385 0.503402 0.094930 0.098 Uiso 1 1 calc R U . . .
O9 O 0.5338(4) 0.2496(3) 0.1053(3) 0.0508(9) Uani 1 1 d G . . . .
H9A H 0.482920 0.289869 0.047402 0.076 Uiso 1 1 d G U . . .
H9B H 0.487737 0.223826 0.151151 0.076 Uiso 1 1 d G U . . .
C1 C 0.4904(4) 0.7203(3) 0.2598(4) 0.0247(7) Uani 1 1 d . . . . .
H1A H 0.496687 0.725463 0.172786 0.030 Uiso 1 1 calc R U . . .
H1B H 0.467576 0.790636 0.284240 0.030 Uiso 1 1 calc R U . . .
C2 C 0.6299(4) 0.6886(3) 0.3505(4) 0.0233(7) Uani 1 1 d . . . . .
H2A H 0.698237 0.738358 0.340355 0.028 Uiso 1 1 calc R U . . .
H2B H 0.628394 0.693193 0.439045 0.028 Uiso 1 1 calc R U . . .
C3 C 0.6694(3) 0.5763(3) 0.3240(4) 0.0230(7) Uani 1 1 d . . . . .
H3 H 0.753519 0.555016 0.390875 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5567(4) 0.4963(3) 0.3185(4) 0.0245(7) Uani 1 1 d . . . . .
H4A H 0.550304 0.486483 0.404903 0.029 Uiso 1 1 calc R U . . .
H4B H 0.581322 0.428108 0.289648 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4161(4) 0.5298(3) 0.2284(4) 0.0248(8) Uani 1 1 d . . . . .
H5 H 0.422403 0.531177 0.140322 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3099(4) 0.4451(3) 0.2317(4) 0.0289(8) Uani 1 1 d . . . . .
H6A H 0.225878 0.458742 0.162518 0.035 Uiso 1 1 calc R U . . .
H6B H 0.343349 0.375319 0.217030 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2798(4) 0.4446(3) 0.3603(4) 0.0274(8) Uani 1 1 d . . . . .
H7A H 0.361195 0.422865 0.428373 0.033 Uiso 1 1 calc R U . . .
H7B H 0.208205 0.393182 0.356799 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2347(3) 0.5553(3) 0.3920(4) 0.0217(7) Uani 1 1 d . . . . .
H8A H 0.151611 0.573120 0.321854 0.026 Uiso 1 1 calc R U . . .
C9 C 0.3415(3) 0.6421(3) 0.3903(4) 0.0216(7) Uani 1 1 d . . . . .
H9 H 0.426603 0.623091 0.457305 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3734(4) 0.6434(3) 0.2583(4) 0.0241(7) Uani 1 1 d . . . . .
C11 C 0.2964(4) 0.7507(3) 0.4273(4) 0.0245(7) Uani 1 1 d . . . . .
H11A H 0.368730 0.802308 0.434701 0.029 Uiso 1 1 calc R U . . .
H11B H 0.216207 0.774532 0.359310 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2631(3) 0.7464(3) 0.5546(4) 0.0232(7) Uani 1 1 d . . . . .
H12A H 0.233859 0.816672 0.572700 0.028 Uiso 1 1 calc R U . . .
H12B H 0.345731 0.728645 0.623501 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1510(3) 0.6649(3) 0.5554(4) 0.0201(7) Uani 1 1 d . . . . .
C14 C 0.1940(3) 0.5537(3) 0.5164(3) 0.0212(7) Uani 1 1 d . . . . .
C15 C 0.3037(4) 0.5174(3) 0.6406(4) 0.0258(8) Uani 1 1 d . . . . .
H15A H 0.314623 0.440489 0.641496 0.031 Uiso 1 1 calc R U . . .
H15B H 0.391115 0.550453 0.647678 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2510(4) 0.5536(3) 0.7513(4) 0.0270(8) Uani 1 1 d . . . . .
H16 H 0.327244 0.576486 0.825624 0.032 Uiso 1 1 calc R U . . .
C17 C 0.1516(4) 0.6485(3) 0.6983(4) 0.0229(7) Uani 1 1 d . . . . .
H17 H 0.194892 0.712011 0.746261 0.027 Uiso 1 1 calc R U . . .
C18 C 0.0137(3) 0.7039(3) 0.4654(4) 0.0228(7) Uani 1 1 d . . . . .
H18A H 0.020010 0.712635 0.379705 0.034 Uiso 1 1 calc R U . . .
H18B H -0.009075 0.771059 0.496004 0.034 Uiso 1 1 calc R U . . .
H18C H -0.056060 0.652520 0.463935 0.034 Uiso 1 1 calc R U . . .
C19 C 0.2473(4) 0.6781(3) 0.1459(4) 0.0314(8) Uani 1 1 d . . . . .
H19A H 0.168858 0.637880 0.148975 0.047 Uiso 1 1 calc R U . . .
H19B H 0.264241 0.665149 0.065145 0.047 Uiso 1 1 calc R U . . .
H19C H 0.230613 0.752765 0.153726 0.047 Uiso 1 1 calc R U . . .
C20 C 0.0131(4) 0.6382(3) 0.7189(3) 0.0218(7) Uani 1 1 d . . . . .
C21 C -0.0288(4) 0.7133(3) 0.7845(4) 0.0264(8) Uani 1 1 d . . . . .
H21 H 0.032235 0.767510 0.822175 0.032 Uiso 1 1 calc R U . . .
C22 C -0.0831(4) 0.5530(3) 0.6673(4) 0.0264(7) Uani 1 1 d . . . . .
H22 H -0.057224 0.495727 0.625591 0.032 Uiso 1 1 calc R U . . .
C23 C -0.2108(4) 0.5557(3) 0.6790(4) 0.0278(8) Uani 1 1 d . . . . .
H23 H -0.271003 0.499931 0.645416 0.033 Uiso 1 1 calc R U . . .
C24 C -0.2544(4) 0.6418(4) 0.7414(4) 0.0345(9) Uani 1 1 d . . . . .
C25 C 0.2426(5) 0.3956(4) 0.8736(4) 0.0387(10) Uani 1 1 d . . . . .
C26 C 0.1505(7) 0.3158(4) 0.9040(5) 0.0527(14) Uani 1 1 d . . . . .
H26A H 0.063773 0.348309 0.896401 0.079 Uiso 1 1 calc R U . . .
H26B H 0.190589 0.290148 0.990560 0.079 Uiso 1 1 calc R U . . .
H26C H 0.137423 0.257139 0.844576 0.079 Uiso 1 1 calc R U . . .
C1' C 0.7900(4) 0.5152(4) 0.1807(4) 0.0323(9) Uani 1 1 d . . . . .
C2' C 0.7898(5) 0.5128(5) 0.0407(5) 0.0493(13) Uani 1 1 d . . . . .
H2' H 0.775135 0.586335 0.008838 0.059 Uiso 1 1 calc R U . . .
C3' C 0.6778(6) 0.4508(5) -0.0386(5) 0.0560(14) Uani 1 1 d . . . . .
H3'A H 0.683552 0.447317 -0.124890 0.084 Uiso 1 1 calc R U . . .
H3'B H 0.592945 0.483701 -0.039908 0.084 Uiso 1 1 calc R U . . .
H3'C H 0.681923 0.380004 -0.003881 0.084 Uiso 1 1 calc R U . . .


_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
O1 C1' 1.322(5) . ?
O1 C3 1.473(4) . ?
O2 C14 1.443(4) . ?
O2 H2 0.8200 . ?
O3 C25 1.331(5) . ?
O3 C16 1.464(5) . ?
O4 C25 1.203(6) . ?
O5 C21 1.366(4) . ?
O5 C24 1.378(5) . ?
O6 C24 1.205(5) . ?
O7 C1' 1.216(5) . ?
O8 C2' 1.405(6) . ?
O8 H8 0.8200 . ?
O9 H9A 0.8501 . ?
O9 H9B 0.8497 . ?
C1 C2 1.522(5) . ?
C1 C10 1.537(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.517(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.519(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.534(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.531(5) . ?
C5 C10 1.553(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.523(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.535(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.533(5) . ?
C8 C9 1.549(4) . ?
C8 H8A 0.9800 . ?
C9 C11 1.530(5) . ?
C9 C10 1.568(5) . ?
C9 H9 0.9800 . ?
C10 C19 1.545(5) . ?
C11 C12 1.525(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.541(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.529(5) . ?
C13 C14 1.559(5) . ?
C13 C17 1.567(5) . ?
C14 C15 1.539(5) . ?
C15 C16 1.533(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.558(5) . ?
C16 H16 0.9800 . ?
C17 C20 1.513(5) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.329(5) . ?
C20 C22 1.446(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.419(6) . ?
C23 H23 0.9300 . ?
C25 C26 1.483(7) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C1' C2' 1.522(6) . ?
C2' C3' 1.435(8) . ?
C2' H2' 0.9800 . ?
C3' H3'A 0.9600 . ?
C3' H3'B 0.9600 . ?
C3' H3'C 0.9600 . ?

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
C1' O1 C3 117.9(3) . . ?
C14 O2 H2 109.5 . . ?
C25 O3 C16 118.3(3) . . ?
C21 O5 C24 121.4(3) . . ?
C2' O8 H8 109.5 . . ?
H9A O9 H9B 109.5 . . ?
C2 C1 C10 114.9(3) . . ?
C2 C1 H1A 108.5 . . ?
C10 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
C10 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C3 C2 C1 111.9(3) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 C2 107.4(3) . . ?
O1 C3 C4 108.0(3) . . ?
C2 C3 C4 112.0(3) . . ?
O1 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C3 C4 C5 113.7(3) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 109.5(3) . . ?
C6 C5 C10 112.4(3) . . ?
C4 C5 C10 112.8(3) . . ?
C6 C5 H5 107.3 . . ?
C4 C5 H5 107.3 . . ?
C10 C5 H5 107.3 . . ?
C7 C6 C5 111.8(3) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 111.3(3) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C14 C8 C7 111.7(3) . . ?
C14 C8 C9 113.9(3) . . ?
C7 C8 C9 111.6(3) . . ?
C14 C8 H8A 106.4 . . ?
C7 C8 H8A 106.4 . . ?
C9 C8 H8A 106.4 . . ?
C11 C9 C8 110.4(3) . . ?
C11 C9 C10 113.4(3) . . ?
C8 C9 C10 111.5(3) . . ?
C11 C9 H9 107.1 . . ?
C8 C9 H9 107.1 . . ?
C10 C9 H9 107.1 . . ?
C1 C10 C19 107.1(3) . . ?
C1 C10 C5 107.8(3) . . ?
C19 C10 C5 108.3(3) . . ?
C1 C10 C9 112.3(3) . . ?
C19 C10 C9 111.6(3) . . ?
C5 C10 C9 109.5(3) . . ?
C12 C11 C9 112.2(3) . . ?
C12 C11 H11A 109.2 . . ?
C9 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C9 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 113.9(3) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C12 109.2(3) . . ?
C18 C13 C14 113.2(3) . . ?
C12 C13 C14 108.4(3) . . ?
C18 C13 C17 113.5(3) . . ?
C12 C13 C17 108.5(3) . . ?
C14 C13 C17 103.8(3) . . ?
O2 C14 C8 108.6(3) . . ?
O2 C14 C15 103.7(3) . . ?
C8 C14 C15 117.0(3) . . ?
O2 C14 C13 110.6(3) . . ?
C8 C14 C13 113.9(3) . . ?
C15 C14 C13 102.6(3) . . ?
C16 C15 C14 105.2(3) . . ?
C16 C15 H15A 110.7 . . ?
C14 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
O3 C16 C15 110.8(3) . . ?
O3 C16 C17 108.2(3) . . ?
C15 C16 C17 106.5(3) . . ?
O3 C16 H16 110.4 . . ?
C15 C16 H16 110.4 . . ?
C17 C16 H16 110.4 . . ?
C20 C17 C16 114.8(3) . . ?
C20 C17 C13 116.2(3) . . ?
C16 C17 C13 105.6(3) . . ?
C20 C17 H17 106.5 . . ?
C16 C17 H17 106.5 . . ?
C13 C17 H17 106.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 115.8(3) . . ?
C21 C20 C17 119.5(3) . . ?
C22 C20 C17 124.6(3) . . ?
C20 C21 O5 124.2(3) . . ?
C20 C21 H21 117.9 . . ?
O5 C21 H21 117.9 . . ?
C23 C22 C20 120.7(4) . . ?
C23 C22 H22 119.7 . . ?
C20 C22 H22 119.7 . . ?
C22 C23 C24 121.4(4) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
O6 C24 O5 117.3(4) . . ?
O6 C24 C23 126.7(4) . . ?
O5 C24 C23 116.0(3) . . ?
O4 C25 O3 122.5(5) . . ?
O4 C25 C26 125.5(4) . . ?
O3 C25 C26 112.0(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C1' O1 125.4(4) . . ?
O7 C1' C2' 122.4(4) . . ?
O1 C1' C2' 112.1(4) . . ?
O8 C2' C3' 113.6(5) . . ?
O8 C2' C1' 111.0(4) . . ?
C3' C2' C1' 111.5(5) . . ?
O8 C2' H2' 106.8 . . ?
C3' C2' H2' 106.8 . . ?
C1' C2' H2' 106.8 . . ?
C2' C3' H3'A 109.5 . . ?
C2' C3' H3'B 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
C2' C3' H3'C 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 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
C10 C1 C2 C3 54.7(4) . . . . ?
C1' O1 C3 C2 144.8(3) . . . . ?
C1' O1 C3 C4 -94.1(4) . . . . ?
C1 C2 C3 O1 68.1(4) . . . . ?
C1 C2 C3 C4 -50.4(4) . . . . ?
O1 C3 C4 C5 -67.5(4) . . . . ?
C2 C3 C4 C5 50.7(4) . . . . ?
C3 C4 C5 C6 -179.0(3) . . . . ?
C3 C4 C5 C10 -53.0(4) . . . . ?
C4 C5 C6 C7 70.3(4) . . . . ?
C10 C5 C6 C7 -55.9(4) . . . . ?
C5 C6 C7 C8 55.5(4) . . . . ?
C6 C7 C8 C14 175.8(3) . . . . ?
C6 C7 C8 C9 -55.4(4) . . . . ?
C14 C8 C9 C11 -50.2(4) . . . . ?
C7 C8 C9 C11 -177.8(3) . . . . ?
C14 C8 C9 C10 -177.2(3) . . . . ?
C7 C8 C9 C10 55.2(4) . . . . ?
C2 C1 C10 C19 -170.8(3) . . . . ?
C2 C1 C10 C5 -54.4(4) . . . . ?
C2 C1 C10 C9 66.4(4) . . . . ?
C6 C5 C10 C1 176.9(3) . . . . ?
C4 C5 C10 C1 52.5(4) . . . . ?
C6 C5 C10 C19 -67.5(4) . . . . ?
C4 C5 C10 C19 168.1(3) . . . . ?
C6 C5 C10 C9 54.4(4) . . . . ?
C4 C5 C10 C9 -70.0(4) . . . . ?
C11 C9 C10 C1 61.0(4) . . . . ?
C8 C9 C10 C1 -173.7(3) . . . . ?
C11 C9 C10 C19 -59.3(4) . . . . ?
C8 C9 C10 C19 66.0(4) . . . . ?
C11 C9 C10 C5 -179.2(3) . . . . ?
C8 C9 C10 C5 -53.9(4) . . . . ?
C8 C9 C11 C12 52.9(4) . . . . ?
C10 C9 C11 C12 178.7(3) . . . . ?
C9 C11 C12 C13 -57.6(4) . . . . ?
C11 C12 C13 C18 -69.3(4) . . . . ?
C11 C12 C13 C14 54.4(4) . . . . ?
C11 C12 C13 C17 166.5(3) . . . . ?
C7 C8 C14 O2 -57.9(4) . . . . ?
C9 C8 C14 O2 174.5(3) . . . . ?
C7 C8 C14 C15 58.9(4) . . . . ?
C9 C8 C14 C15 -68.6(4) . . . . ?
C7 C8 C14 C13 178.4(3) . . . . ?
C9 C8 C14 C13 50.9(4) . . . . ?
C18 C13 C14 O2 -52.1(4) . . . . ?
C12 C13 C14 O2 -173.4(3) . . . . ?
C17 C13 C14 O2 71.4(3) . . . . ?
C18 C13 C14 C8 70.5(4) . . . . ?
C12 C13 C14 C8 -50.8(4) . . . . ?
C17 C13 C14 C8 -166.0(3) . . . . ?
C18 C13 C14 C15 -162.1(3) . . . . ?
C12 C13 C14 C15 76.6(3) . . . . ?
C17 C13 C14 C15 -38.6(3) . . . . ?
O2 C14 C15 C16 -76.2(3) . . . . ?
C8 C14 C15 C16 164.3(3) . . . . ?
C13 C14 C15 C16 38.9(3) . . . . ?
C25 O3 C16 C15 85.2(4) . . . . ?
C25 O3 C16 C17 -158.3(3) . . . . ?
C14 C15 C16 O3 93.5(3) . . . . ?
C14 C15 C16 C17 -24.0(4) . . . . ?
O3 C16 C17 C20 9.7(4) . . . . ?
C15 C16 C17 C20 129.0(3) . . . . ?
O3 C16 C17 C13 -119.6(3) . . . . ?
C15 C16 C17 C13 -0.4(4) . . . . ?
C18 C13 C17 C20 18.9(4) . . . . ?
C12 C13 C17 C20 140.4(3) . . . . ?
C14 C13 C17 C20 -104.4(3) . . . . ?
C18 C13 C17 C16 147.4(3) . . . . ?
C12 C13 C17 C16 -91.0(3) . . . . ?
C14 C13 C17 C16 24.1(3) . . . . ?
C16 C17 C20 C21 122.0(4) . . . . ?
C13 C17 C20 C21 -114.1(4) . . . . ?
C16 C17 C20 C22 -60.7(5) . . . . ?
C13 C17 C20 C22 63.2(4) . . . . ?
C22 C20 C21 O5 -2.8(5) . . . . ?
C17 C20 C21 O5 174.8(3) . . . . ?
C24 O5 C21 C20 -3.7(6) . . . . ?
C21 C20 C22 C23 4.4(5) . . . . ?
C17 C20 C22 C23 -173.1(3) . . . . ?
C20 C22 C23 C24 0.3(6) . . . . ?
C21 O5 C24 O6 -173.1(4) . . . . ?
C21 O5 C24 C23 8.1(6) . . . . ?
C22 C23 C24 O6 174.9(5) . . . . ?
C22 C23 C24 O5 -6.4(6) . . . . ?
C16 O3 C25 O4 -1.5(6) . . . . ?
C16 O3 C25 C26 178.9(3) . . . . ?
C3 O1 C1' O7 -7.3(6) . . . . ?
C3 O1 C1' C2' 172.2(4) . . . . ?
O7 C1' C2' O8 -22.1(7) . . . . ?
O1 C1' C2' O8 158.4(5) . . . . ?
O7 C1' C2' C3' 105.6(6) . . . . ?
O1 C1' C2' C3' -73.9(6) . . . . ?

_refine_diff_density_max         1.520
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.059

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TE-2
_database_code_depnum_ccdc_archive 'CCDC 1546637'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H38 O9'
_chemical_formula_weight         506.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   32.2353(3)
_cell_length_b                   7.66968(8)
_cell_length_c                   10.48751(13)
_cell_angle_alpha                90.0
_cell_angle_beta                 99.2221(11)
_cell_angle_gamma                90.0
_cell_volume                     2559.37(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    15778
_cell_measurement_theta_min      4.2610
_cell_measurement_theta_max      73.3440

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.811
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_reflns_number            18236
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.2708
_diffrn_reflns_theta_max         73.6524
_diffrn_reflns_theta_full        66.9682
_diffrn_measured_fraction_theta_max 0.9799
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5075
_reflns_number_gt                5044
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.993

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XP (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+2.0346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration re
_refine_ls_number_reflns         5075
_refine_ls_number_parameters     335
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      6.195
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42487(6) 0.3333(3) 0.24369(17) 0.0254(4) Uani 1 1 d . . . . .
O2 O 0.36028(5) 0.2035(2) 0.69940(17) 0.0207(4) Uani 1 1 d . . . . .
H2 H 0.337941 0.213975 0.650154 0.031 Uiso 1 1 calc DR U . . .
O3 O 0.30849(6) 0.3520(3) 0.83162(19) 0.0273(4) Uani 1 1 d . . . . .
O4 O 0.37174(6) 0.9064(2) 0.84433(16) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.367945 0.990404 0.795501 0.032 Uiso 1 1 calc DR U . . .
O5 O 0.27976(7) 0.7159(3) 1.2408(2) 0.0378(5) Uani 1 1 d . . . . .
O6 O 0.27890(6) 0.9360(3) 1.38144(17) 0.0285(4) Uani 1 1 d . . . . .
O7 O 0.38018(6) 0.1883(3) 0.0922(2) 0.0336(5) Uani 1 1 d . . . . .
O8 O 0.44516(6) 0.1005(3) -0.03305(19) 0.0345(5) Uani 1 1 d . . . . .
H8 H 0.423922 0.039942 -0.043756 0.052 Uiso 1 1 calc R U . . .
O9 O 0.28834(6) 0.2539(3) 0.52513(19) 0.0320(5) Uani 1 1 d G . . . .
H9A H 0.266577 0.287962 0.554372 0.048 Uiso 1 1 d G U . . .
H9B H 0.282254 0.165311 0.477158 0.048 Uiso 1 1 d G U . . .
C1 C 0.41965(9) 0.2573(4) 0.5221(3) 0.0266(6) Uani 1 1 d . . . . .
H1A H 0.445616 0.227707 0.491506 0.032 Uiso 1 1 calc R U . . .
H1B H 0.414767 0.169386 0.584481 0.032 Uiso 1 1 calc R U . . .
C2 C 0.38374(10) 0.2504(4) 0.4081(3) 0.0290(6) Uani 1 1 d . . . . .
H2A H 0.382700 0.135375 0.369215 0.035 Uiso 1 1 calc R U . . .
H2B H 0.357297 0.270250 0.438733 0.035 Uiso 1 1 calc R U . . .
C3 C 0.38935(9) 0.3859(4) 0.3076(2) 0.0257(6) Uani 1 1 d . . . . .
H3 H 0.363711 0.392538 0.243430 0.031 Uiso 1 1 calc R U . . .
C4 C 0.39945(9) 0.5654(4) 0.3661(3) 0.0269(6) Uani 1 1 d . . . . .
H4A H 0.373925 0.614870 0.388884 0.032 Uiso 1 1 calc R U . . .
H4B H 0.408363 0.640013 0.300920 0.032 Uiso 1 1 calc R U . . .
C5 C 0.43368(9) 0.5676(3) 0.4867(3) 0.0236(5) Uani 1 1 d . . . . .
H5 H 0.460007 0.532650 0.458459 0.028 Uiso 1 1 calc R U . . .
C6 C 0.44040(11) 0.7523(4) 0.5420(3) 0.0372(7) Uani 1 1 d . . . . .
H6A H 0.466092 0.755494 0.604365 0.045 Uiso 1 1 calc R U . . .
H6B H 0.443463 0.833003 0.472905 0.045 Uiso 1 1 calc R U . . .
C7 C 0.40356(12) 0.8090(4) 0.6072(3) 0.0367(7) Uani 1 1 d . . . . .
H7A H 0.409971 0.921537 0.647827 0.044 Uiso 1 1 calc R U . . .
H7B H 0.378862 0.823098 0.541764 0.044 Uiso 1 1 calc R U . . .
C8 C 0.39355(8) 0.6800(3) 0.7087(2) 0.0211(5) Uani 1 1 d . . . . .
H8A H 0.418564 0.673066 0.775298 0.025 Uiso 1 1 calc R U . . .
C9 C 0.38593(8) 0.4950(3) 0.6508(2) 0.0169(4) Uani 1 1 d . . . . .
H9 H 0.362093 0.502756 0.580134 0.020 Uiso 1 1 calc R U . . .
C10 C 0.42516(8) 0.4341(4) 0.5902(2) 0.0210(5) Uani 1 1 d . . . . .
C11 C 0.37326(7) 0.3679(3) 0.7520(2) 0.0167(5) Uani 1 1 d . . . . .
H11 H 0.398173 0.348840 0.817386 0.020 Uiso 1 1 calc R U . . .
C12 C 0.33879(8) 0.4419(3) 0.8213(2) 0.0176(5) Uani 1 1 d . . . . .
C13 C 0.34413(7) 0.6266(3) 0.8768(2) 0.0159(5) Uani 1 1 d . . . . .
C14 C 0.35750(8) 0.7508(3) 0.7750(2) 0.0181(5) Uani 1 1 d . . . . .
C15 C 0.31572(8) 0.7864(3) 0.6877(2) 0.0226(5) Uani 1 1 d . . . . .
H15A H 0.306517 0.685794 0.634557 0.027 Uiso 1 1 calc R U . . .
H15B H 0.317776 0.886234 0.632301 0.027 Uiso 1 1 calc R U . . .
C16 C 0.28595(8) 0.8233(4) 0.7845(2) 0.0266(6) Uani 1 1 d . . . . .
H16A H 0.256999 0.802242 0.745738 0.032 Uiso 1 1 calc R U . . .
H16B H 0.288656 0.943118 0.814215 0.032 Uiso 1 1 calc R U . . .
C17 C 0.29972(7) 0.6956(4) 0.8973(2) 0.0204(5) Uani 1 1 d . . . . .
H17 H 0.280465 0.596045 0.884007 0.024 Uiso 1 1 calc R U . . .
C18 C 0.37681(8) 0.6175(3) 1.0004(2) 0.0201(5) Uani 1 1 d . . . . .
H18A H 0.367082 0.539640 1.060865 0.030 Uiso 1 1 calc R U . . .
H18B H 0.380816 0.731664 1.037842 0.030 Uiso 1 1 calc R U . . .
H18C H 0.402987 0.575531 0.979612 0.030 Uiso 1 1 calc R U . . .
C19 C 0.46400(9) 0.4167(5) 0.6954(3) 0.0339(7) Uani 1 1 d . . . . .
H19A H 0.469571 0.526440 0.738781 0.051 Uiso 1 1 calc R U . . .
H19B H 0.487813 0.383440 0.656419 0.051 Uiso 1 1 calc R U . . .
H19C H 0.458896 0.329400 0.756564 0.051 Uiso 1 1 calc R U . . .
C20 C 0.29699(7) 0.7680(3) 1.0298(2) 0.0187(5) Uani 1 1 d . . . . .
C21 C 0.28439(9) 0.6590(4) 1.1212(3) 0.0276(6) Uani 1 1 d . . . . .
H21 H 0.278889 0.542613 1.100160 0.033 Uiso 1 1 calc R U . . .
C22 C 0.30679(9) 0.9382(4) 1.0685(2) 0.0245(5) Uani 1 1 d . . . . .
H22 H 0.317174 1.014127 1.012068 0.029 Uiso 1 1 calc R U . . .
C23 C 0.30143(8) 0.9960(3) 1.1880(2) 0.0186(5) Uani 1 1 d . . . . .
H23 H 0.307828 1.111222 1.210640 0.022 Uiso 1 1 calc R U . . .
C24 C 0.28649(8) 0.8856(4) 1.2775(2) 0.0235(5) Uani 1 1 d . . . . .
C1' C 0.41545(8) 0.2263(4) 0.1418(2) 0.0243(5) Uani 1 1 d . . . . .
C2' C 0.45441(9) 0.1523(4) 0.0979(2) 0.0255(6) Uani 1 1 d . . . . .
H2' H 0.475660 0.244617 0.104764 0.031 Uiso 1 1 calc R U . . .
C3' C 0.47169(10) 0.0047(5) 0.1877(3) 0.0379(7) Uani 1 1 d . . . . .
H3'A H 0.451372 -0.087609 0.182228 0.057 Uiso 1 1 calc R U . . .
H3'B H 0.477460 0.047166 0.274859 0.057 Uiso 1 1 calc R U . . .
H3'C H 0.497155 -0.038622 0.162749 0.057 Uiso 1 1 calc R U . . .


_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
O1 C1' 1.343(3) . ?
O1 C3 1.473(3) . ?
O2 C11 1.413(3) . ?
O2 H2 0.8200 . ?
O3 C12 1.215(3) . ?
O4 C14 1.434(3) . ?
O4 H4 0.8200 . ?
O5 C21 1.359(3) . ?
O5 C24 1.364(4) . ?
O6 C24 1.218(3) . ?
O7 C1' 1.208(3) . ?
O8 C2' 1.415(3) . ?
O8 H8 0.8200 . ?
O9 H9A 0.8506 . ?
O9 H9B 0.8497 . ?
C1 C2 1.525(4) . ?
C1 C10 1.530(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.512(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.521(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.539(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.533(4) . ?
C5 C10 1.549(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.526(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.526(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.548(3) . ?
C8 C14 1.545(3) . ?
C8 H8A 0.9800 . ?
C9 C11 1.543(3) . ?
C9 C10 1.574(3) . ?
C9 H9 0.9800 . ?
C10 C19 1.536(4) . ?
C11 C12 1.531(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.531(3) . ?
C13 C18 1.535(3) . ?
C13 C14 1.544(3) . ?
C13 C17 1.573(3) . ?
C14 C15 1.527(3) . ?
C15 C16 1.531(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.545(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C20 1.512(3) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.381(4) . ?
C20 C22 1.388(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.405(4) . ?
C23 H23 0.9300 . ?
C1' C2' 1.516(4) . ?
C2' C3' 1.520(4) . ?
C2' H2' 0.9800 . ?
C3' H3'A 0.9600 . ?
C3' H3'B 0.9600 . ?
C3' H3'C 0.9600 . ?

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
C1' O1 C3 115.9(2) . . ?
C11 O2 H2 109.5 . . ?
C14 O4 H4 109.5 . . ?
C21 O5 C24 122.0(2) . . ?
C2' O8 H8 109.5 . . ?
H9A O9 H9B 109.5 . . ?
C2 C1 C10 114.4(2) . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 111.2(2) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C2 108.5(2) . . ?
O1 C3 C4 107.5(2) . . ?
C2 C3 C4 112.5(2) . . ?
O1 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
C3 C4 C5 114.9(2) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.5 . . ?
C6 C5 C4 111.1(2) . . ?
C6 C5 C10 112.1(2) . . ?
C4 C5 C10 112.6(2) . . ?
C6 C5 H5 106.9 . . ?
C4 C5 H5 106.9 . . ?
C10 C5 H5 106.9 . . ?
C7 C6 C5 111.1(2) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 113.2(3) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 111.0(2) . . ?
C7 C8 C14 110.1(2) . . ?
C9 C8 C14 114.6(2) . . ?
C7 C8 H8A 106.9 . . ?
C9 C8 H8A 106.9 . . ?
C14 C8 H8A 106.9 . . ?
C11 C9 C8 110.61(18) . . ?
C11 C9 C10 114.11(19) . . ?
C8 C9 C10 110.0(2) . . ?
C11 C9 H9 107.3 . . ?
C8 C9 H9 107.3 . . ?
C10 C9 H9 107.3 . . ?
C1 C10 C19 106.2(2) . . ?
C1 C10 C5 106.17(19) . . ?
C19 C10 C5 110.2(2) . . ?
C1 C10 C9 114.2(2) . . ?
C19 C10 C9 110.6(2) . . ?
C5 C10 C9 109.3(2) . . ?
O2 C11 C12 108.89(19) . . ?
O2 C11 C9 112.95(18) . . ?
C12 C11 C9 112.63(19) . . ?
O2 C11 H11 107.4 . . ?
C12 C11 H11 107.4 . . ?
C9 C11 H11 107.4 . . ?
O3 C12 C11 119.2(2) . . ?
O3 C12 C13 122.3(2) . . ?
C11 C12 C13 118.5(2) . . ?
C12 C13 C18 107.41(19) . . ?
C12 C13 C14 109.56(18) . . ?
C18 C13 C14 112.46(19) . . ?
C12 C13 C17 108.32(19) . . ?
C18 C13 C17 114.64(19) . . ?
C14 C13 C17 104.33(19) . . ?
O4 C14 C15 109.6(2) . . ?
O4 C14 C13 105.35(18) . . ?
C15 C14 C13 101.99(19) . . ?
O4 C14 C8 108.55(19) . . ?
C15 C14 C8 116.6(2) . . ?
C13 C14 C8 114.06(19) . . ?
C14 C15 C16 102.83(19) . . ?
C14 C15 H15A 111.2 . . ?
C16 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C16 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C15 C16 C17 104.9(2) . . ?
C15 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.8 . . ?
C20 C17 C16 114.8(2) . . ?
C20 C17 C13 115.92(19) . . ?
C16 C17 C13 105.37(19) . . ?
C20 C17 H17 106.7 . . ?
C16 C17 H17 106.7 . . ?
C13 C17 H17 106.7 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 116.4(2) . . ?
C21 C20 C17 118.9(2) . . ?
C22 C20 C17 124.7(2) . . ?
O5 C21 C20 122.3(3) . . ?
O5 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
C23 C22 C20 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
C20 C22 H22 119.4 . . ?
C22 C23 C24 121.6(2) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
O6 C24 O5 120.6(3) . . ?
O6 C24 C23 123.1(3) . . ?
O5 C24 C23 116.3(2) . . ?
O7 C1' O1 124.6(3) . . ?
O7 C1' C2' 123.2(2) . . ?
O1 C1' C2' 112.2(2) . . ?
O8 C2' C1' 110.1(2) . . ?
O8 C2' C3' 113.1(3) . . ?
C1' C2' C3' 109.3(2) . . ?
O8 C2' H2' 108.1 . . ?
C1' C2' H2' 108.1 . . ?
C3' C2' H2' 108.1 . . ?
C2' C3' H3'A 109.5 . . ?
C2' C3' H3'B 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
C2' C3' H3'C 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 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
C10 C1 C2 C3 57.9(3) . . . . ?
C1' O1 C3 C2 87.3(3) . . . . ?
C1' O1 C3 C4 -150.8(2) . . . . ?
C1 C2 C3 O1 70.4(3) . . . . ?
C1 C2 C3 C4 -48.3(3) . . . . ?
O1 C3 C4 C5 -72.8(3) . . . . ?
C2 C3 C4 C5 46.6(3) . . . . ?
C3 C4 C5 C6 -177.6(2) . . . . ?
C3 C4 C5 C10 -51.0(3) . . . . ?
C4 C5 C6 C7 72.2(3) . . . . ?
C10 C5 C6 C7 -54.7(3) . . . . ?
C5 C6 C7 C8 53.5(4) . . . . ?
C6 C7 C8 C9 -54.9(3) . . . . ?
C6 C7 C8 C14 177.1(3) . . . . ?
C7 C8 C9 C11 -176.6(2) . . . . ?
C14 C8 C9 C11 -51.1(3) . . . . ?
C7 C8 C9 C10 56.4(3) . . . . ?
C14 C8 C9 C10 -178.1(2) . . . . ?
C2 C1 C10 C19 -176.8(2) . . . . ?
C2 C1 C10 C5 -59.5(3) . . . . ?
C2 C1 C10 C9 61.1(3) . . . . ?
C6 C5 C10 C1 -179.4(2) . . . . ?
C4 C5 C10 C1 54.5(3) . . . . ?
C6 C5 C10 C19 -64.8(3) . . . . ?
C4 C5 C10 C19 169.1(2) . . . . ?
C6 C5 C10 C9 57.0(3) . . . . ?
C4 C5 C10 C9 -69.2(3) . . . . ?
C11 C9 C10 C1 58.9(3) . . . . ?
C8 C9 C10 C1 -176.1(2) . . . . ?
C11 C9 C10 C19 -60.8(3) . . . . ?
C8 C9 C10 C19 64.2(3) . . . . ?
C11 C9 C10 C5 177.7(2) . . . . ?
C8 C9 C10 C5 -57.3(2) . . . . ?
C8 C9 C11 O2 171.72(19) . . . . ?
C10 C9 C11 O2 -63.6(3) . . . . ?
C8 C9 C11 C12 47.8(3) . . . . ?
C10 C9 C11 C12 172.5(2) . . . . ?
O2 C11 C12 O3 5.7(3) . . . . ?
C9 C11 C12 O3 131.8(2) . . . . ?
O2 C11 C12 C13 -175.05(18) . . . . ?
C9 C11 C12 C13 -48.9(3) . . . . ?
O3 C12 C13 C18 103.8(3) . . . . ?
C11 C12 C13 C18 -75.4(2) . . . . ?
O3 C12 C13 C14 -133.8(2) . . . . ?
C11 C12 C13 C14 47.0(3) . . . . ?
O3 C12 C13 C17 -20.5(3) . . . . ?
C11 C12 C13 C17 160.26(19) . . . . ?
C12 C13 C14 O4 -165.97(18) . . . . ?
C18 C13 C14 O4 -46.6(2) . . . . ?
C17 C13 C14 O4 78.2(2) . . . . ?
C12 C13 C14 C15 79.6(2) . . . . ?
C18 C13 C14 C15 -161.06(19) . . . . ?
C17 C13 C14 C15 -36.2(2) . . . . ?
C12 C13 C14 C8 -47.0(3) . . . . ?
C18 C13 C14 C8 72.3(3) . . . . ?
C17 C13 C14 C8 -162.8(2) . . . . ?
C7 C8 C14 O4 -64.6(3) . . . . ?
C9 C8 C14 O4 169.37(18) . . . . ?
C7 C8 C14 C15 59.7(3) . . . . ?
C9 C8 C14 C15 -66.3(3) . . . . ?
C7 C8 C14 C13 178.3(2) . . . . ?
C9 C8 C14 C13 52.3(3) . . . . ?
O4 C14 C15 C16 -65.5(2) . . . . ?
C13 C14 C15 C16 45.8(2) . . . . ?
C8 C14 C15 C16 170.7(2) . . . . ?
C14 C15 C16 C17 -37.6(3) . . . . ?
C15 C16 C17 C20 143.4(2) . . . . ?
C15 C16 C17 C13 14.6(3) . . . . ?
C12 C13 C17 C20 128.6(2) . . . . ?
C18 C13 C17 C20 8.7(3) . . . . ?
C14 C13 C17 C20 -114.8(2) . . . . ?
C12 C13 C17 C16 -103.3(2) . . . . ?
C18 C13 C17 C16 136.8(2) . . . . ?
C14 C13 C17 C16 13.3(2) . . . . ?
C16 C17 C20 C21 142.7(2) . . . . ?
C13 C17 C20 C21 -94.0(3) . . . . ?
C16 C17 C20 C22 -38.1(3) . . . . ?
C13 C17 C20 C22 85.2(3) . . . . ?
C24 O5 C21 C20 1.3(4) . . . . ?
C22 C20 C21 O5 3.1(4) . . . . ?
C17 C20 C21 O5 -177.6(2) . . . . ?
C21 C20 C22 C23 -4.2(4) . . . . ?
C17 C20 C22 C23 176.6(2) . . . . ?
C20 C22 C23 C24 1.1(4) . . . . ?
C21 O5 C24 O6 174.1(3) . . . . ?
C21 O5 C24 C23 -4.4(4) . . . . ?
C22 C23 C24 O6 -175.2(3) . . . . ?
C22 C23 C24 O5 3.3(4) . . . . ?
C3 O1 C1' O7 8.7(4) . . . . ?
C3 O1 C1' C2' -169.3(2) . . . . ?
O7 C1' C2' O8 25.1(4) . . . . ?
O1 C1' C2' O8 -156.9(2) . . . . ?
O7 C1' C2' C3' -99.6(3) . . . . ?
O1 C1' C2' C3' 78.3(3) . . . . ?

_refine_diff_density_max         0.790
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.051

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compd1
_database_code_depnum_ccdc_archive 'CCDC 1546636'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H36 O8'
_chemical_formula_weight         488.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.26417(6)
_cell_length_b                   18.04765(14)
_cell_length_c                   10.53779(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.2643(9)
_cell_angle_gamma                90
_cell_volume                     1191.043(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7920
_cell_measurement_theta_min      4.8470
_cell_measurement_theta_max      73.4900

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.820
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91008
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_reflns_number            10324
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.196
_diffrn_reflns_theta_max         73.630
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4548
_reflns_number_gt                4480
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_max     0.903
_reflns_Friedel_fraction_full    0.956

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+0.1883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2014 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4548
_refine_ls_number_parameters     323
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0647
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6248(2) 0.63147(9) -0.06430(13) 0.0292(3) Uani 1 1 d . . . . .
O2 O 0.8593(2) 0.62670(7) 0.47062(12) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.9777 0.6220 0.5044 0.029 Uiso 1 1 calc R U . . .
O3 O 1.0712(2) 0.51720(7) 0.57067(12) 0.0197(3) Uani 1 1 d . . . . .
O4 O 0.5016(2) 0.34768(7) 0.52116(12) 0.0198(3) Uani 1 1 d . . . . .
H4 H 0.4842 0.3125 0.4727 0.030 Uiso 1 1 calc R U . . .
O5 O 1.1196(3) 0.33760(9) 0.96381(14) 0.0349(4) Uani 1 1 d . . . . .
O6 O 0.9711(4) 0.28319(11) 1.12788(15) 0.0496(5) Uani 1 1 d . . . . .
O7 O 0.8233(2) 0.61663(7) -0.23843(12) 0.0226(3) Uani 1 1 d . . . . .
O8 O 0.5974(2) 0.72163(7) -0.36684(12) 0.0235(3) Uani 1 1 d . . . . .
H8 H 0.6917 0.6934 -0.3899 0.035 Uiso 1 1 calc R U . . .
C1 C 0.6842(3) 0.64379(10) 0.21279(18) 0.0222(4) Uani 1 1 d . . . . .
H1A H 0.5919 0.6796 0.1703 0.027 Uiso 1 1 calc R U . . .
H1B H 0.7548 0.6688 0.2836 0.027 Uiso 1 1 calc R U . . .
C2 C 0.8530(3) 0.61832(13) 0.12041(19) 0.0286(4) Uani 1 1 d . . . . .
H2A H 0.9308 0.6611 0.0904 0.034 Uiso 1 1 calc R U . . .
H2B H 0.9538 0.5860 0.1645 0.034 Uiso 1 1 calc R U . . .
C3 C 0.7557(3) 0.57755(12) 0.00815(19) 0.0278(4) Uani 1 1 d . . . . .
H3 H 0.8686 0.5579 -0.0452 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6126(3) 0.51521(11) 0.05125(17) 0.0254(4) Uani 1 1 d . . . . .
H4A H 0.7009 0.4764 0.0885 0.030 Uiso 1 1 calc R U . . .
H4B H 0.5388 0.4945 -0.0224 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4456(3) 0.53906(10) 0.14849(17) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.3488 0.5740 0.1052 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3111(3) 0.47225(10) 0.18741(19) 0.0234(4) Uani 1 1 d . . . . .
H6A H 0.1904 0.4893 0.2356 0.028 Uiso 1 1 calc R U . . .
H6B H 0.2559 0.4475 0.1118 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4412(3) 0.41733(10) 0.26727(18) 0.0216(4) Uani 1 1 d . . . . .
H7A H 0.5548 0.3970 0.2168 0.026 Uiso 1 1 calc R U . . .
H7B H 0.3501 0.3767 0.2927 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5378(3) 0.45491(9) 0.38596(16) 0.0163(3) Uani 1 1 d . . . . .
H8A H 0.4172 0.4727 0.4352 0.020 Uiso 1 1 calc R U . . .
C9 C 0.6715(3) 0.52449(9) 0.35222(16) 0.0154(3) Uani 1 1 d . . . . .
H9 H 0.7985 0.5083 0.3072 0.019 Uiso 1 1 calc R U . . .
C10 C 0.5445(3) 0.58032(10) 0.26524(17) 0.0171(3) Uani 1 1 d . . . . .
C11 C 0.7445(3) 0.55937(9) 0.48069(16) 0.0163(3) Uani 1 1 d . . . . .
H11 H 0.6178 0.5685 0.5313 0.020 Uiso 1 1 calc R U . . .
C12 C 0.8840(3) 0.50278(9) 0.54991(16) 0.0159(3) Uani 1 1 d . . . . .
C13 C 0.7780(3) 0.43055(9) 0.58836(16) 0.0158(3) Uani 1 1 d . . . . .
C14 C 0.6567(3) 0.39732(9) 0.47039(17) 0.0164(3) Uani 1 1 d . . . . .
C15 C 0.8319(3) 0.35219(10) 0.40711(17) 0.0192(4) Uani 1 1 d . . . . .
H15A H 0.9323 0.3842 0.3648 0.023 Uiso 1 1 calc R U . . .
H15B H 0.7717 0.3174 0.3460 0.023 Uiso 1 1 calc R U . . .
C16 C 0.9393(3) 0.31174(10) 0.51926(18) 0.0209(4) Uani 1 1 d . . . . .
H16A H 1.0796 0.2938 0.4972 0.025 Uiso 1 1 calc R U . . .
H16B H 0.8532 0.2702 0.5464 0.025 Uiso 1 1 calc R U . . .
C17 C 0.9554(3) 0.37158(10) 0.62371(17) 0.0184(4) Uani 1 1 d . . . . .
H17 H 1.0934 0.3963 0.6139 0.022 Uiso 1 1 calc R U . . .
C18 C 0.6261(3) 0.45009(10) 0.69629(17) 0.0196(4) Uani 1 1 d . . . . .
H18A H 0.7061 0.4722 0.7652 0.029 Uiso 1 1 calc R U . . .
H18B H 0.5577 0.4058 0.7255 0.029 Uiso 1 1 calc R U . . .
H18C H 0.5199 0.4844 0.6655 0.029 Uiso 1 1 calc R U . . .
C19 C 0.3662(3) 0.61722(11) 0.34017(18) 0.0223(4) Uani 1 1 d . . . . .
H19A H 0.4278 0.6510 0.4011 0.033 Uiso 1 1 calc R U . . .
H19B H 0.2864 0.5799 0.3835 0.033 Uiso 1 1 calc R U . . .
H19C H 0.2728 0.6438 0.2828 0.033 Uiso 1 1 calc R U . . .
C20 C 0.9517(3) 0.34302(10) 0.75778(17) 0.0201(4) Uani 1 1 d . . . . .
C21 C 1.1103(3) 0.35980(11) 0.83971(19) 0.0277(4) Uani 1 1 d . . . . .
H21 H 1.2221 0.3885 0.8103 0.033 Uiso 1 1 calc R U . . .
C22 C 0.7813(3) 0.29847(10) 0.80685(18) 0.0227(4) Uani 1 1 d . . . . .
H22 H 0.6698 0.2835 0.7530 0.027 Uiso 1 1 calc R U . . .
C23 C 0.7817(4) 0.27819(11) 0.9301(2) 0.0282(4) Uani 1 1 d . . . . .
H23 H 0.6680 0.2506 0.9601 0.034 Uiso 1 1 calc R U . . .
C24 C 0.9537(4) 0.29815(12) 1.01659(19) 0.0318(5) Uani 1 1 d . . . . .
C1' C 0.6768(3) 0.64489(10) -0.18462(17) 0.0184(4) Uani 1 1 d . . . . .
C2' C 0.5183(3) 0.69710(10) -0.24854(17) 0.0197(4) Uani 1 1 d . . . . .
H2' H 0.4978 0.7402 -0.1936 0.024 Uiso 1 1 calc R U . . .
C3' C 0.3057(3) 0.65730(11) -0.2668(2) 0.0261(4) Uani 1 1 d . . . . .
H3'1 H 0.2058 0.6895 -0.3098 0.039 Uiso 1 1 calc R U . . .
H3'2 H 0.2513 0.6439 -0.1855 0.039 Uiso 1 1 calc R U . . .
H3'3 H 0.3259 0.6134 -0.3166 0.039 Uiso 1 1 calc R U . . .


_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
O1 C1' 1.338(2) . ?
O1 C3 1.475(2) . ?
O2 C11 1.417(2) . ?
O2 H2 0.8200 . ?
O3 C12 1.216(2) . ?
O4 C14 1.434(2) . ?
O4 H4 0.8200 . ?
O5 C21 1.368(2) . ?
O5 C24 1.386(3) . ?
O6 C24 1.206(3) . ?
O7 C1' 1.202(2) . ?
O8 C2' 1.422(2) . ?
O8 H8 0.8200 . ?
C1 C2 1.524(3) . ?
C1 C10 1.551(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.510(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.515(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.541(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.532(3) . ?
C5 C10 1.555(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.525(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.535(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.548(2) . ?
C8 C9 1.555(2) . ?
C8 H8A 0.9800 . ?
C9 C11 1.553(2) . ?
C9 C10 1.567(2) . ?
C9 H9 0.9800 . ?
C10 C19 1.534(2) . ?
C11 C12 1.520(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.522(2) . ?
C13 C18 1.540(2) . ?
C13 C14 1.562(2) . ?
C13 C17 1.578(2) . ?
C14 C15 1.532(2) . ?
C15 C16 1.532(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.544(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C20 1.505(2) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.337(3) . ?
C20 C22 1.442(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.350(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.441(3) . ?
C23 H23 0.9300 . ?
C1' C2' 1.516(2) . ?
C2' C3' 1.521(3) . ?
C2' H2' 0.9800 . ?
C3' H3'1 0.9600 . ?
C3' H3'2 0.9600 . ?
C3' H3'3 0.9600 . ?

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
C1' O1 C3 117.76(15) . . ?
C11 O2 H2 109.5 . . ?
C14 O4 H4 109.5 . . ?
C21 O5 C24 121.19(16) . . ?
C2' O8 H8 109.5 . . ?
C2 C1 C10 114.19(16) . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 111.96(16) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 C2 107.10(17) . . ?
O1 C3 C4 108.63(16) . . ?
C2 C3 C4 111.00(16) . . ?
O1 C3 H3 110.0 . . ?
C2 C3 H3 110.0 . . ?
C4 C3 H3 110.0 . . ?
C3 C4 C5 114.00(17) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 110.09(15) . . ?
C6 C5 C10 112.14(14) . . ?
C4 C5 C10 113.30(15) . . ?
C6 C5 H5 107.0 . . ?
C4 C5 H5 107.0 . . ?
C10 C5 H5 107.0 . . ?
C7 C6 C5 111.64(16) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 111.03(15) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C14 110.34(14) . . ?
C7 C8 C9 112.03(14) . . ?
C14 C8 C9 114.76(14) . . ?
C7 C8 H8A 106.4 . . ?
C14 C8 H8A 106.4 . . ?
C9 C8 H8A 106.4 . . ?
C11 C9 C8 106.13(13) . . ?
C11 C9 C10 112.66(14) . . ?
C8 C9 C10 112.58(14) . . ?
C11 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C19 C10 C1 106.61(15) . . ?
C19 C10 C5 109.47(14) . . ?
C1 C10 C5 106.84(14) . . ?
C19 C10 C9 110.12(14) . . ?
C1 C10 C9 113.59(14) . . ?
C5 C10 C9 110.06(14) . . ?
O2 C11 C12 108.96(14) . . ?
O2 C11 C9 115.00(14) . . ?
C12 C11 C9 107.53(13) . . ?
O2 C11 H11 108.4 . . ?
C12 C11 H11 108.4 . . ?
C9 C11 H11 108.4 . . ?
O3 C12 C11 118.97(15) . . ?
O3 C12 C13 124.05(16) . . ?
C11 C12 C13 116.98(14) . . ?
C12 C13 C18 106.31(13) . . ?
C12 C13 C14 108.93(13) . . ?
C18 C13 C14 112.23(14) . . ?
C12 C13 C17 109.34(14) . . ?
C18 C13 C17 115.07(14) . . ?
C14 C13 C17 104.87(13) . . ?
O4 C14 C15 109.16(13) . . ?
O4 C14 C8 108.21(14) . . ?
C15 C14 C8 116.56(14) . . ?
O4 C14 C13 105.34(13) . . ?
C15 C14 C13 102.13(13) . . ?
C8 C14 C13 114.76(13) . . ?
C14 C15 C16 102.95(14) . . ?
C14 C15 H15A 111.2 . . ?
C16 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C16 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C15 C16 C17 103.74(14) . . ?
C15 C16 H16A 111.0 . . ?
C17 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
C17 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
C20 C17 C16 115.33(15) . . ?
C20 C17 C13 115.30(15) . . ?
C16 C17 C13 105.59(14) . . ?
C20 C17 H17 106.7 . . ?
C16 C17 H17 106.7 . . ?
C13 C17 H17 106.7 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 116.14(18) . . ?
C21 C20 C17 120.15(18) . . ?
C22 C20 C17 123.70(16) . . ?
C20 C21 O5 124.50(19) . . ?
C20 C21 H21 117.8 . . ?
O5 C21 H21 117.8 . . ?
C23 C22 C20 120.72(18) . . ?
C23 C22 H22 119.6 . . ?
C20 C22 H22 119.6 . . ?
C22 C23 C24 121.7(2) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
O6 C24 O5 116.9(2) . . ?
O6 C24 C23 127.5(2) . . ?
O5 C24 C23 115.55(17) . . ?
O7 C1' O1 125.05(17) . . ?
O7 C1' C2' 123.59(16) . . ?
O1 C1' C2' 111.26(15) . . ?
O8 C2' C1' 110.19(14) . . ?
O8 C2' C3' 110.93(15) . . ?
C1' C2' C3' 109.00(15) . . ?
O8 C2' H2' 108.9 . . ?
C1' C2' H2' 108.9 . . ?
C3' C2' H2' 108.9 . . ?
C2' C3' H3'1 109.5 . . ?
C2' C3' H3'2 109.5 . . ?
H3'1 C3' H3'2 109.5 . . ?
C2' C3' H3'3 109.5 . . ?
H3'1 C3' H3'3 109.5 . . ?
H3'2 C3' H3'3 109.5 . . ?

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
C10 C1 C2 C3 57.5(2) . . . . ?
C1' O1 C3 C2 119.37(18) . . . . ?
C1' O1 C3 C4 -120.68(18) . . . . ?
C1 C2 C3 O1 65.76(19) . . . . ?
C1 C2 C3 C4 -52.7(2) . . . . ?
O1 C3 C4 C5 -66.3(2) . . . . ?
C2 C3 C4 C5 51.2(2) . . . . ?
C3 C4 C5 C6 -179.26(15) . . . . ?
C3 C4 C5 C10 -52.8(2) . . . . ?
C4 C5 C6 C7 69.65(19) . . . . ?
C10 C5 C6 C7 -57.5(2) . . . . ?
C5 C6 C7 C8 57.1(2) . . . . ?
C6 C7 C8 C14 176.25(15) . . . . ?
C6 C7 C8 C9 -54.6(2) . . . . ?
C7 C8 C9 C11 176.08(14) . . . . ?
C14 C8 C9 C11 -57.08(18) . . . . ?
C7 C8 C9 C10 52.39(19) . . . . ?
C14 C8 C9 C10 179.23(14) . . . . ?
C2 C1 C10 C19 -172.13(15) . . . . ?
C2 C1 C10 C5 -55.15(19) . . . . ?
C2 C1 C10 C9 66.4(2) . . . . ?
C6 C5 C10 C19 -67.59(19) . . . . ?
C4 C5 C10 C19 167.03(15) . . . . ?
C6 C5 C10 C1 177.34(15) . . . . ?
C4 C5 C10 C1 51.95(19) . . . . ?
C6 C5 C10 C9 53.58(19) . . . . ?
C4 C5 C10 C9 -71.80(18) . . . . ?
C11 C9 C10 C19 -50.31(19) . . . . ?
C8 C9 C10 C19 69.67(18) . . . . ?
C11 C9 C10 C1 69.17(19) . . . . ?
C8 C9 C10 C1 -170.84(14) . . . . ?
C11 C9 C10 C5 -171.09(14) . . . . ?
C8 C9 C10 C5 -51.10(18) . . . . ?
C8 C9 C11 O2 -176.40(13) . . . . ?
C10 C9 C11 O2 -52.8(2) . . . . ?
C8 C9 C11 C12 62.05(17) . . . . ?
C10 C9 C11 C12 -174.31(14) . . . . ?
O2 C11 C12 O3 -9.5(2) . . . . ?
C9 C11 C12 O3 115.72(17) . . . . ?
O2 C11 C12 C13 170.84(13) . . . . ?
C9 C11 C12 C13 -63.91(19) . . . . ?
O3 C12 C13 C18 109.83(18) . . . . ?
C11 C12 C13 C18 -70.56(18) . . . . ?
O3 C12 C13 C14 -129.03(17) . . . . ?
C11 C12 C13 C14 50.58(19) . . . . ?
O3 C12 C13 C17 -15.0(2) . . . . ?
C11 C12 C13 C17 164.65(14) . . . . ?
C7 C8 C14 O4 -67.64(17) . . . . ?
C9 C8 C14 O4 164.66(13) . . . . ?
C7 C8 C14 C15 55.8(2) . . . . ?
C9 C8 C14 C15 -71.92(19) . . . . ?
C7 C8 C14 C13 175.07(14) . . . . ?
C9 C8 C14 C13 47.38(19) . . . . ?
C12 C13 C14 O4 -159.06(13) . . . . ?
C18 C13 C14 O4 -41.62(17) . . . . ?
C17 C13 C14 O4 83.98(15) . . . . ?
C12 C13 C14 C15 86.92(15) . . . . ?
C18 C13 C14 C15 -155.64(14) . . . . ?
C17 C13 C14 C15 -30.04(16) . . . . ?
C12 C13 C14 C8 -40.15(19) . . . . ?
C18 C13 C14 C8 77.29(18) . . . . ?
C17 C13 C14 C8 -157.11(14) . . . . ?
O4 C14 C15 C16 -66.32(17) . . . . ?
C8 C14 C15 C16 170.75(14) . . . . ?
C13 C14 C15 C16 44.85(15) . . . . ?
C14 C15 C16 C17 -42.38(17) . . . . ?
C15 C16 C17 C20 151.35(15) . . . . ?
C15 C16 C17 C13 22.82(18) . . . . ?
C12 C13 C17 C20 119.32(16) . . . . ?
C18 C13 C17 C20 -0.2(2) . . . . ?
C14 C13 C17 C20 -124.01(16) . . . . ?
C12 C13 C17 C16 -112.14(15) . . . . ?
C18 C13 C17 C16 128.34(16) . . . . ?
C14 C13 C17 C16 4.53(17) . . . . ?
C16 C17 C20 C21 124.3(2) . . . . ?
C13 C17 C20 C21 -112.2(2) . . . . ?
C16 C17 C20 C22 -57.0(2) . . . . ?
C13 C17 C20 C22 66.5(2) . . . . ?
C22 C20 C21 O5 0.1(3) . . . . ?
C17 C20 C21 O5 178.84(18) . . . . ?
C24 O5 C21 C20 -3.6(3) . . . . ?
C21 C20 C22 C23 2.6(3) . . . . ?
C17 C20 C22 C23 -176.15(18) . . . . ?
C20 C22 C23 C24 -1.8(3) . . . . ?
C21 O5 C24 O6 -177.3(2) . . . . ?
C21 O5 C24 C23 4.2(3) . . . . ?
C22 C23 C24 O6 -180.0(2) . . . . ?
C22 C23 C24 O5 -1.6(3) . . . . ?
C3 O1 C1' O7 -0.4(3) . . . . ?
C3 O1 C1' C2' 175.92(16) . . . . ?
O7 C1' C2' O8 -14.6(2) . . . . ?
O1 C1' C2' O8 168.95(15) . . . . ?
O7 C1' C2' C3' 107.3(2) . . . . ?
O1 C1' C2' C3' -69.10(19) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TE-5
_database_code_depnum_ccdc_archive 'CCDC 1546639'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H38 N0 O8'
_chemical_formula_weight         490.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.4990(2)
_cell_length_b                   10.4196(3)
_cell_length_c                   12.8765(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.497(3)
_cell_angle_gamma                90
_cell_volume                     1266.28(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2161
_cell_measurement_theta_min      3.4460
_cell_measurement_theta_max      62.7430

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.771
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_reflns_number            5345
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.4546
_diffrn_reflns_theta_max         62.7167
_diffrn_reflns_theta_full        63.5953
_diffrn_measured_fraction_theta_max 0.9949
_diffrn_measured_fraction_theta_full 0.9679
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.784
_diffrn_reflns_point_group_measured_fraction_full 0.784
_reflns_number_total             3166
_reflns_number_gt                2590
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.484
_reflns_Friedel_fraction_max     0.545
_reflns_Friedel_fraction_full    0.545

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO '
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XP (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0908P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 765 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(14)
_chemical_absolute_configuration re
_refine_ls_number_reflns         3166
_refine_ls_number_parameters     324
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1203(3) 0.5059(3) -0.0037(2) 0.0593(7) Uani 1 1 d . . . . .
O2 O 0.3035(3) 0.2905(3) 0.0561(2) 0.0589(8) Uani 1 1 d . . . . .
H2 H 0.228176 0.323354 0.032590 0.088 Uiso 1 1 calc R U . . .
O3 O 0.9020(3) 0.4930(3) 0.3062(2) 0.0629(8) Uani 1 1 d . . . . .
O4 O 1.1143(4) 0.6768(4) 0.6991(3) 0.0810(10) Uani 1 1 d . . . . .
O5 O 1.3117(5) 0.5697(5) 0.7498(4) 0.1144(16) Uani 1 1 d . . . . .
O6 O -0.0226(4) 0.6784(3) -0.0178(4) 0.0950(14) Uani 1 1 d . . . . .
O7 O -0.2486(3) 0.5256(4) -0.0896(4) 0.0927(13) Uani 1 1 d . . . . .
H7 H -0.244307 0.602427 -0.075636 0.139 Uiso 1 1 calc R U . . .
C1 C 0.2294(4) 0.4748(6) 0.2202(4) 0.0684(13) Uani 1 1 d . . . . .
H1A H 0.156433 0.416544 0.189797 0.082 Uiso 1 1 calc R U . . .
H1B H 0.213702 0.489203 0.292369 0.082 Uiso 1 1 calc R U . . .
C2 C 0.2138(4) 0.6006(5) 0.1626(4) 0.0672(13) Uani 1 1 d . . . . .
H2A H 0.281718 0.661783 0.195520 0.081 Uiso 1 1 calc R U . . .
H2B H 0.119468 0.634635 0.166513 0.081 Uiso 1 1 calc R U . . .
C3 C 0.2378(4) 0.5838(4) 0.0486(4) 0.0617(12) Uani 1 1 d . . . . .
H3 H 0.239619 0.667860 0.014701 0.074 Uiso 1 1 calc R U . . .
C4 C 0.3739(4) 0.5115(4) 0.0364(3) 0.0515(9) Uani 1 1 d . . . . .
H4A H 0.453146 0.569031 0.054838 0.062 Uiso 1 1 calc R U . . .
H4B H 0.374141 0.489096 -0.036679 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3985(4) 0.3888(4) 0.1018(3) 0.0483(9) Uani 1 1 d . . . . .
C6 C 0.5462(4) 0.3348(4) 0.0933(3) 0.0542(10) Uani 1 1 d . . . . .
H6A H 0.551456 0.248412 0.121525 0.065 Uiso 1 1 calc R U . . .
H6B H 0.560681 0.329489 0.020047 0.065 Uiso 1 1 calc R U . . .
C7 C 0.6648(4) 0.4151(5) 0.1506(3) 0.0534(10) Uani 1 1 d . . . . .
H7A H 0.669713 0.496871 0.115221 0.064 Uiso 1 1 calc R U . . .
H7B H 0.754364 0.371300 0.147769 0.064 Uiso 1 1 calc R U . . .
C8 C 0.6434(4) 0.4392(4) 0.2648(3) 0.0479(9) Uani 1 1 d . . . . .
H8 H 0.646195 0.356046 0.300540 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4956(4) 0.4988(4) 0.2711(3) 0.0502(9) Uani 1 1 d . . . . .
H9 H 0.492144 0.578538 0.230547 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3747(4) 0.4100(4) 0.2181(3) 0.0522(10) Uani 1 1 d . . . . .
C11 C 0.4757(4) 0.5360(6) 0.3836(3) 0.0694(13) Uani 1 1 d . . . . .
H11A H 0.384781 0.578114 0.384474 0.083 Uiso 1 1 calc R U . . .
H11B H 0.475276 0.458943 0.425922 0.083 Uiso 1 1 calc R U . . .
O8 O 0.5446(7) 0.3861(8) 0.7676(8) 0.178(3) Uani 1 1 d G . . . .
H8A H 0.610662 0.440228 0.782844 0.267 Uiso 1 1 d G U . . .
H8B H 0.467190 0.425713 0.750342 0.267 Uiso 1 1 d G U . . .
C12 C 0.5929(4) 0.6253(6) 0.4309(4) 0.0686(12) Uani 1 1 d . . . . .
H12A H 0.576214 0.646785 0.501732 0.082 Uiso 1 1 calc R U . . .
H12B H 0.589557 0.704199 0.390734 0.082 Uiso 1 1 calc R U . . .
C13 C 0.7424(4) 0.5649(4) 0.4327(3) 0.0536(10) Uani 1 1 d . . . . .
C14 C 0.7564(4) 0.5234(4) 0.3213(3) 0.0491(9) Uani 1 1 d . . . . .
C15 C 0.8443(5) 0.6161(5) 0.2732(4) 0.0651(11) Uani 1 1 d . . . . .
H15 H 0.824362 0.634948 0.198389 0.078 Uiso 1 1 calc R U . . .
C16 C 0.8873(6) 0.7221(5) 0.3479(4) 0.0756(14) Uani 1 1 d . . . . .
H16A H 0.834804 0.799688 0.327753 0.091 Uiso 1 1 calc R U . . .
H16B H 0.987730 0.739938 0.349077 0.091 Uiso 1 1 calc R U . . .
C17 C 0.8538(5) 0.6761(4) 0.4564(3) 0.0586(10) Uani 1 1 d . . . . .
H17 H 0.804842 0.746731 0.487396 0.070 Uiso 1 1 calc R U . . .
C18 C 0.7614(5) 0.4554(5) 0.5102(4) 0.0700(13) Uani 1 1 d . . . . .
H18A H 0.683330 0.396855 0.497250 0.105 Uiso 1 1 calc R U . . .
H18B H 0.764459 0.488728 0.579912 0.105 Uiso 1 1 calc R U . . .
H18C H 0.848265 0.411244 0.502540 0.105 Uiso 1 1 calc R U . . .
C19 C 0.3710(5) 0.2813(6) 0.2753(4) 0.0735(13) Uani 1 1 d . . . . .
H19A H 0.295048 0.229698 0.242102 0.110 Uiso 1 1 calc R U . . .
H19B H 0.356228 0.296148 0.346808 0.110 Uiso 1 1 calc R U . . .
H19C H 0.459334 0.237309 0.272685 0.110 Uiso 1 1 calc R U . . .
C20 C 0.9843(4) 0.6458(5) 0.5307(3) 0.0594(11) Uani 1 1 d . . . . .
C21 C 1.0016(5) 0.6996(5) 0.6263(4) 0.0659(12) Uani 1 1 d . . . . .
H21 H 0.932140 0.756035 0.643722 0.079 Uiso 1 1 calc R U . . .
C22 C 1.0958(5) 0.5638(6) 0.5066(4) 0.0720(13) Uani 1 1 d . . . . .
H22 H 1.090459 0.526167 0.440764 0.086 Uiso 1 1 calc R U . . .
C23 C 1.2083(5) 0.5394(5) 0.5764(4) 0.0737(13) Uani 1 1 d . . . . .
H23 H 1.280203 0.486595 0.557602 0.088 Uiso 1 1 calc R U . . .
C24 C 1.2198(5) 0.5931(5) 0.6788(4) 0.0730(14) Uani 1 1 d . . . . .
C1' C -0.0032(5) 0.5660(4) -0.0303(4) 0.0633(12) Uani 1 1 d . . . . .
C2' C -0.1123(4) 0.4745(4) -0.0808(4) 0.0588(11) Uani 1 1 d . . . . .
H2' H -0.112056 0.399078 -0.035279 0.071 Uiso 1 1 calc R U . . .
C3' C -0.0714(7) 0.4296(8) -0.1838(5) 0.099(2) Uani 1 1 d . . . . .
H3'A H -0.137197 0.365346 -0.212254 0.148 Uiso 1 1 calc R U . . .
H3'B H 0.022273 0.393852 -0.173882 0.148 Uiso 1 1 calc R U . . .
H3'C H -0.073142 0.500900 -0.231120 0.148 Uiso 1 1 calc R U . . .


_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
O1 C1' 1.340(5) . ?
O1 C3 1.479(5) . ?
O2 C5 1.445(4) . ?
O2 H2 0.8200 . ?
O3 C15 1.440(6) . ?
O3 C14 1.454(5) . ?
O4 C21 1.362(6) . ?
O4 C24 1.375(7) . ?
O5 C24 1.215(6) . ?
O6 C1' 1.200(6) . ?
O7 C2' 1.392(5) . ?
O7 H7 0.8200 . ?
C1 C2 1.505(8) . ?
C1 C10 1.539(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.521(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.520(6) . ?
C3 H3 0.9800 . ?
C4 C5 1.535(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.527(5) . ?
C5 C10 1.555(6) . ?
C6 C7 1.525(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.527(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.508(5) . ?
C8 C9 1.545(5) . ?
C8 H8 0.9800 . ?
C9 C11 1.533(6) . ?
C9 C10 1.569(5) . ?
C9 H9 0.9800 . ?
C10 C19 1.533(7) . ?
C11 C12 1.524(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O8 H8A 0.8498 . ?
O8 H8B 0.8502 . ?
C12 C13 1.551(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.513(7) . ?
C13 C14 1.518(6) . ?
C13 C17 1.575(6) . ?
C14 C15 1.460(6) . ?
C15 C16 1.492(7) . ?
C15 H15 0.9800 . ?
C16 C17 1.543(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C20 1.511(6) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.345(7) . ?
C20 C22 1.422(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.341(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.425(8) . ?
C23 H23 0.9300 . ?
C1' C2' 1.501(6) . ?
C2' C3' 1.498(7) . ?
C2' H2' 0.9800 . ?
C3' H3'A 0.9600 . ?
C3' H3'B 0.9600 . ?
C3' H3'C 0.9600 . ?

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
C1' O1 C3 117.0(3) . . ?
C5 O2 H2 109.5 . . ?
C15 O3 C14 60.6(3) . . ?
C21 O4 C24 120.8(4) . . ?
C2' O7 H7 109.5 . . ?
C2 C1 C10 114.4(4) . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C3 111.0(4) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C4 106.8(3) . . ?
O1 C3 C2 108.3(4) . . ?
C4 C3 C2 112.3(3) . . ?
O1 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
C3 C4 C5 115.7(3) . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
C5 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
O2 C5 C6 104.2(3) . . ?
O2 C5 C4 108.5(3) . . ?
C6 C5 C4 110.6(3) . . ?
O2 C5 C10 109.9(3) . . ?
C6 C5 C10 110.9(3) . . ?
C4 C5 C10 112.4(3) . . ?
C7 C6 C5 113.4(3) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 112.6(3) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C14 C8 C7 113.3(3) . . ?
C14 C8 C9 110.0(3) . . ?
C7 C8 C9 109.7(3) . . ?
C14 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C11 C9 C8 111.2(3) . . ?
C11 C9 C10 113.4(3) . . ?
C8 C9 C10 111.4(3) . . ?
C11 C9 H9 106.8 . . ?
C8 C9 H9 106.8 . . ?
C10 C9 H9 106.8 . . ?
C19 C10 C1 107.8(4) . . ?
C19 C10 C5 110.6(4) . . ?
C1 C10 C5 107.9(3) . . ?
C19 C10 C9 111.3(3) . . ?
C1 C10 C9 110.3(4) . . ?
C5 C10 C9 108.9(3) . . ?
C12 C11 C9 111.6(4) . . ?
C12 C11 H11A 109.3 . . ?
C9 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C9 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
H8A O8 H8B 109.5 . . ?
C11 C12 C13 112.6(4) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C18 C13 C14 113.1(4) . . ?
C18 C13 C12 110.8(4) . . ?
C14 C13 C12 106.2(3) . . ?
C18 C13 C17 113.6(3) . . ?
C14 C13 C17 105.3(3) . . ?
C12 C13 C17 107.4(4) . . ?
O3 C14 C15 59.2(3) . . ?
O3 C14 C8 116.4(3) . . ?
C15 C14 C8 126.1(4) . . ?
O3 C14 C13 112.0(3) . . ?
C15 C14 C13 109.1(4) . . ?
C8 C14 C13 119.2(3) . . ?
O3 C15 C14 60.2(3) . . ?
O3 C15 C16 113.6(4) . . ?
C14 C15 C16 110.1(4) . . ?
O3 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 106.5(4) . . ?
C15 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C20 C17 C16 113.6(4) . . ?
C20 C17 C13 117.0(4) . . ?
C16 C17 C13 104.8(3) . . ?
C20 C17 H17 107.0 . . ?
C16 C17 H17 107.0 . . ?
C13 C17 H17 107.0 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 115.7(4) . . ?
C21 C20 C17 119.9(4) . . ?
C22 C20 C17 124.4(4) . . ?
C20 C21 O4 124.2(5) . . ?
C20 C21 H21 117.9 . . ?
O4 C21 H21 117.9 . . ?
C23 C22 C20 121.6(5) . . ?
C23 C22 H22 119.2 . . ?
C20 C22 H22 119.2 . . ?
C22 C23 C24 121.2(5) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
O5 C24 O4 117.4(5) . . ?
O5 C24 C23 126.2(6) . . ?
O4 C24 C23 116.4(4) . . ?
O6 C1' O1 124.5(4) . . ?
O6 C1' C2' 124.7(4) . . ?
O1 C1' C2' 110.8(4) . . ?
O7 C2' C3' 112.3(4) . . ?
O7 C2' C1' 112.5(4) . . ?
C3' C2' C1' 110.2(4) . . ?
O7 C2' H2' 107.2 . . ?
C3' C2' H2' 107.2 . . ?
C1' C2' H2' 107.2 . . ?
C2' C3' H3'A 109.5 . . ?
C2' C3' H3'B 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
C2' C3' H3'C 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 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
C10 C1 C2 C3 58.3(5) . . . . ?
C1' O1 C3 C4 -160.6(4) . . . . ?
C1' O1 C3 C2 78.2(5) . . . . ?
C1 C2 C3 O1 67.5(4) . . . . ?
C1 C2 C3 C4 -50.1(5) . . . . ?
O1 C3 C4 C5 -71.6(4) . . . . ?
C2 C3 C4 C5 47.0(5) . . . . ?
C3 C4 C5 O2 73.4(4) . . . . ?
C3 C4 C5 C6 -172.9(3) . . . . ?
C3 C4 C5 C10 -48.4(4) . . . . ?
O2 C5 C6 C7 -172.1(3) . . . . ?
C4 C5 C6 C7 71.5(4) . . . . ?
C10 C5 C6 C7 -53.8(5) . . . . ?
C5 C6 C7 C8 53.3(5) . . . . ?
C6 C7 C8 C14 -177.4(3) . . . . ?
C6 C7 C8 C9 -54.1(5) . . . . ?
C14 C8 C9 C11 -49.4(5) . . . . ?
C7 C8 C9 C11 -174.7(4) . . . . ?
C14 C8 C9 C10 -177.0(3) . . . . ?
C7 C8 C9 C10 57.7(4) . . . . ?
C2 C1 C10 C19 -177.4(4) . . . . ?
C2 C1 C10 C5 -57.9(5) . . . . ?
C2 C1 C10 C9 60.9(5) . . . . ?
O2 C5 C10 C19 47.7(4) . . . . ?
C6 C5 C10 C19 -67.0(4) . . . . ?
C4 C5 C10 C19 168.7(3) . . . . ?
O2 C5 C10 C1 -70.0(4) . . . . ?
C6 C5 C10 C1 175.3(4) . . . . ?
C4 C5 C10 C1 51.0(4) . . . . ?
O2 C5 C10 C9 170.3(3) . . . . ?
C6 C5 C10 C9 55.5(5) . . . . ?
C4 C5 C10 C9 -68.8(4) . . . . ?
C11 C9 C10 C19 -62.9(5) . . . . ?
C8 C9 C10 C19 63.4(5) . . . . ?
C11 C9 C10 C1 56.7(5) . . . . ?
C8 C9 C10 C1 -176.9(3) . . . . ?
C11 C9 C10 C5 174.9(4) . . . . ?
C8 C9 C10 C5 -58.7(4) . . . . ?
C8 C9 C11 C12 55.2(6) . . . . ?
C10 C9 C11 C12 -178.3(4) . . . . ?
C9 C11 C12 C13 -59.0(6) . . . . ?
C11 C12 C13 C18 -69.1(5) . . . . ?
C11 C12 C13 C14 54.0(5) . . . . ?
C11 C12 C13 C17 166.3(4) . . . . ?
C15 O3 C14 C8 118.1(4) . . . . ?
C15 O3 C14 C13 -99.9(4) . . . . ?
C7 C8 C14 O3 -45.9(5) . . . . ?
C9 C8 C14 O3 -169.1(3) . . . . ?
C7 C8 C14 C15 24.0(6) . . . . ?
C9 C8 C14 C15 -99.2(5) . . . . ?
C7 C8 C14 C13 174.9(4) . . . . ?
C9 C8 C14 C13 51.7(5) . . . . ?
C18 C13 C14 O3 -71.8(5) . . . . ?
C12 C13 C14 O3 166.5(4) . . . . ?
C17 C13 C14 O3 52.7(4) . . . . ?
C18 C13 C14 C15 -135.5(4) . . . . ?
C12 C13 C14 C15 102.8(4) . . . . ?
C17 C13 C14 C15 -10.9(4) . . . . ?
C18 C13 C14 C8 69.1(4) . . . . ?
C12 C13 C14 C8 -52.7(5) . . . . ?
C17 C13 C14 C8 -166.4(3) . . . . ?
C14 O3 C15 C16 100.5(4) . . . . ?
C8 C14 C15 O3 -101.9(4) . . . . ?
C13 C14 C15 O3 104.7(3) . . . . ?
O3 C14 C15 C16 -106.4(4) . . . . ?
C8 C14 C15 C16 151.7(4) . . . . ?
C13 C14 C15 C16 -1.7(5) . . . . ?
O3 C15 C16 C17 -51.4(5) . . . . ?
C14 C15 C16 C17 13.9(5) . . . . ?
C15 C16 C17 C20 109.0(5) . . . . ?
C15 C16 C17 C13 -19.9(5) . . . . ?
C18 C13 C17 C20 16.2(6) . . . . ?
C14 C13 C17 C20 -108.1(4) . . . . ?
C12 C13 C17 C20 139.1(4) . . . . ?
C18 C13 C17 C16 143.0(4) . . . . ?
C14 C13 C17 C16 18.8(5) . . . . ?
C12 C13 C17 C16 -94.1(4) . . . . ?
C16 C17 C20 C21 127.4(5) . . . . ?
C13 C17 C20 C21 -110.2(5) . . . . ?
C16 C17 C20 C22 -51.5(6) . . . . ?
C13 C17 C20 C22 70.9(6) . . . . ?
C22 C20 C21 O4 -2.1(7) . . . . ?
C17 C20 C21 O4 179.0(5) . . . . ?
C24 O4 C21 C20 -0.9(8) . . . . ?
C21 C20 C22 C23 1.9(8) . . . . ?
C17 C20 C22 C23 -179.2(5) . . . . ?
C20 C22 C23 C24 1.2(9) . . . . ?
C21 O4 C24 O5 -174.6(5) . . . . ?
C21 O4 C24 C23 3.9(7) . . . . ?
C22 C23 C24 O5 174.3(6) . . . . ?
C22 C23 C24 O4 -4.0(8) . . . . ?
C3 O1 C1' O6 2.7(8) . . . . ?
C3 O1 C1' C2' -179.1(4) . . . . ?
O6 C1' C2' O7 -14.4(8) . . . . ?
O1 C1' C2' O7 167.4(4) . . . . ?
O6 C1' C2' C3' 111.7(7) . . . . ?
O1 C1' C2' C3' -66.5(6) . . . . ?

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.039

