# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_dzt2921
_database_code_depnum_ccdc_archive 'CCDC 2239741'
loop_
_audit_author_name
_audit_author_address
'bipodonine A'
;Yunnan University
China
;
_audit_update_record             
;
2023-02-03 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '2(C16 H26 O5), 3(H2 O)'
_chemical_formula_sum            'C32 H58 O13'
_chemical_formula_iupac          ?
_chemical_formula_weight         650.78
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
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                   23.970(4)
_cell_length_b                   11.3431(18)
_cell_length_c                   6.1596(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.533(6)
_cell_angle_gamma                90
_cell_volume                     1663.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7155
_cell_measurement_theta_min      3.7121
_cell_measurement_theta_max      71.1637
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.320
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708

_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_T_max  0.78

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            5992
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_theta_min         3.71
_diffrn_reflns_theta_max         74.94
_diffrn_reflns_theta_full        74.94
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 0.902
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7

_refine_special_details          
;
;

_reflns_number_total             2805
_reflns_number_gt                2625
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.1238
_refine_ls_wR_factor_gt          0.3929
_refine_ls_wR_factor_ref         0.4205
_refine_ls_goodness_of_fit_ref   2.062
_refine_ls_restrained_S_all      2.062
_refine_ls_number_reflns         2805
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.011
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.410
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.047(13)
_refine_ls_abs_structure_details 
;

Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(13)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O2 0.5492(3) 0.7775(6) 0.4006(10) 0.0667(18) Uani d . . . 1 . .
H H2 0.528621 0.836977 0.408207 0.1 Uiso calc U . R 1 . .
C C2 0.5523(4) 0.4152(11) 0.7889(15) 0.072(3) Uani d . . . 1 . .
H H2A 0.546721 0.431668 0.942872 0.086 Uiso calc U . R 1 . .
H H2AB 0.517812 0.376783 0.718164 0.086 Uiso calc U . R 1 . .
O O1 0.6535(3) 0.3868(5) 0.8515(8) 0.0571(15) Uani d . . . 1 . .
C C1 0.5616(4) 0.5315(8) 0.6719(13) 0.060(2) Uani d . . . 1 . .
H H1A 0.558773 0.517021 0.512508 0.072 Uiso calc U . R 1 . .
H H1AB 0.531647 0.587758 0.699299 0.072 Uiso calc U . R 1 . .
O O3 0.6941(3) 0.8199(6) 0.4601(12) 0.0698(19) Uani d . . . 1 . .
C C3 0.6019(4) 0.3320(9) 0.7828(12) 0.061(2) Uani d . . . 1 . .
H H3 0.602765 0.307185 0.627412 0.073 Uiso calc U . R 1 . .
O O4 0.5451(3) 0.1654(8) 0.8653(12) 0.076(2) Uani d . . . 1 . .
H H4A 0.536656 0.16554 0.729117 0.114 Uiso calc U . R 1 . .
C C4 0.6619(4) 0.4890(6) 0.7167(10) 0.0520(18) Uani d . . . 1 . .
H H4 0.655728 0.462724 0.560855 0.062 Uiso calc U . R 1 . .
O O5 0.6293(4) 0.9451(8) 0.2923(19) 0.107(4) Uani d . . . 1 . .
C C5 0.7231(4) 0.5255(7) 0.7624(12) 0.059(2) Uani d . . . 1 . .
H H5A 0.747756 0.458917 0.732301 0.07 Uiso calc U . R 1 . .
H H5AB 0.73174 0.548116 0.91786 0.07 Uiso calc U . R 1 . .
O O6 0.5 0.0581(16) 0.5 0.204(18) Uani d T P S 1 . .
C C6 0.7339(4) 0.6352(8) 0.6084(15) 0.064(2) Uani d . . . 1 . .
H H6A 0.772796 0.663955 0.644817 0.076 Uiso calc U . R 1 . .
H H6AB 0.729493 0.609346 0.453864 0.076 Uiso calc U . R 1 . .
C C7 0.6947(4) 0.7307(8) 0.6356(13) 0.061(2) Uani d . . . 1 . .
O O7 0.4787(7) 0.8872(17) 0.031(3) 0.142(6) Uani d . . . 1 . .
C C10 0.6410(5) 0.8632(10) 0.4142(19) 0.076(3) Uani d . . . 1 . .
C C11 0.5994(4) 0.2208(9) 0.9184(13) 0.062(2) Uani d . . . 1 . .
C C12 0.6417(4) 0.1267(9) 0.8577(16) 0.068(2) Uani d . . . 1 . .
H H12A 0.635881 0.053259 0.936009 0.102 Uiso calc U . R 1 . .
H H12B 0.680084 0.154966 0.898884 0.102 Uiso calc U . R 1 . .
H H12C 0.635963 0.112145 0.699947 0.102 Uiso calc U . R 1 . .
C C13 0.6076(4) 0.2471(10) 1.1595(12) 0.067(2) Uani d . . . 1 . .
H H13A 0.592176 0.182398 1.2396 0.1 Uiso calc U . R 1 . .
H H13B 0.588278 0.320621 1.188043 0.1 Uiso calc U . R 1 . .
H H13C 0.647826 0.255335 1.207943 0.1 Uiso calc U . R 1 . .
C C15 0.6203(4) 0.6263(10) 0.9852(12) 0.067(2) Uani d . . . 1 . .
H H15A 0.659566 0.633401 1.048247 0.1 Uiso calc U . R 1 . .
H H15B 0.601156 0.568335 1.068705 0.1 Uiso calc U . R 1 . .
H H15C 0.601667 0.702939 0.991116 0.1 Uiso calc U . R 1 . .
C C14 0.7119(5) 0.8051(10) 0.8509(18) 0.078(3) Uani d . . . 1 . .
H H14A 0.717111 0.751953 0.977089 0.118 Uiso calc U . R 1 . .
H H14B 0.682168 0.861996 0.871149 0.118 Uiso calc U . R 1 . .
H H14C 0.747027 0.847236 0.837578 0.118 Uiso calc U . R 1 . .
C C00H 0.6340(4) 0.6830(8) 0.5967(12) 0.057(2) Uani d . . . 1 . .
H H00H 0.633084 0.64242 0.452217 0.068 Uiso calc U . R 1 . .
C C9 0.6004(4) 0.7933(9) 0.5417(13) 0.063(2) Uani d . . . 1 . .
H H9 0.59327 0.836211 0.677622 0.076 Uiso calc U . R 1 . .
C C8 0.6179(4) 0.5857(9) 0.7461(12) 0.062(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C9 . 1.432(11) ?
O2 H2 . 0.84 ?
C2 C3 . 1.523(14) ?
C2 C1 . 1.532(13) ?
C2 H2A . 0.99 ?
C2 H2AB . 0.99 ?
O1 C3 . 1.406(11) ?
O1 C4 . 1.454(9) ?
C1 C8 . 1.506(13) ?
C1 H1A . 0.99 ?
C1 H1AB . 0.99 ?
O3 C10 . 1.364(14) ?
O3 C7 . 1.480(9) ?
C3 C11 . 1.518(12) ?
C3 H3 . 1.0 ?
O4 C11 . 1.448(11) ?
O4 H4A . 0.84 ?
C4 C5 . 1.518(12) ?
C4 C8 . 1.547(12) ?
C4 H4 . 1.0 ?
O5 C10 . 1.207(13) ?
C5 C6 . 1.603(13) ?
C5 H5A . 0.99 ?
C5 H5AB . 0.99 ?
C6 C7 . 1.455(14) ?
C6 H6A . 0.99 ?
C6 H6AB . 0.99 ?
C7 C00H . 1.545(13) ?
C7 C14 . 1.586(11) ?
O7 O7 2_655 1.13(3) ?
C10 C9 . 1.539(17) ?
C11 C13 . 1.506(10) ?
C11 C12 . 1.548(14) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C15 C8 . 1.538(10) ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C00H C9 . 1.506(12) ?
C00H C8 . 1.514(12) ?
C00H H00H . 1.0 ?
C9 H9 . 1.0 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O2 H2 . . 109.5 ?
C3 C2 C1 . . 111.4(7) ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2AB . . 109.3 ?
C1 C2 H2AB . . 109.3 ?
H2A C2 H2AB . . 108.0 ?
C3 O1 C4 . . 110.8(6) ?
C8 C1 C2 . . 112.5(7) ?
C8 C1 H1A . . 109.1 ?
C2 C1 H1A . . 109.1 ?
C8 C1 H1AB . . 109.1 ?
C2 C1 H1AB . . 109.1 ?
H1A C1 H1AB . . 107.8 ?
C10 O3 C7 . . 109.2(8) ?
O1 C3 C11 . . 106.9(6) ?
O1 C3 C2 . . 112.4(8) ?
C11 C3 C2 . . 114.9(8) ?
O1 C3 H3 . . 107.4 ?
C11 C3 H3 . . 107.4 ?
C2 C3 H3 . . 107.4 ?
C11 O4 H4A . . 109.5 ?
O1 C4 C5 . . 107.8(6) ?
O1 C4 C8 . . 110.9(6) ?
C5 C4 C8 . . 116.2(6) ?
O1 C4 H4 . . 107.2 ?
C5 C4 H4 . . 107.2 ?
C8 C4 H4 . . 107.2 ?
C4 C5 C6 . . 108.6(6) ?
C4 C5 H5A . . 110.0 ?
C6 C5 H5A . . 110.0 ?
C4 C5 H5AB . . 110.0 ?
C6 C5 H5AB . . 110.0 ?
H5A C5 H5AB . . 108.4 ?
C7 C6 C5 . . 111.1(7) ?
C7 C6 H6A . . 109.4 ?
C5 C6 H6A . . 109.4 ?
C7 C6 H6AB . . 109.4 ?
C5 C6 H6AB . . 109.4 ?
H6A C6 H6AB . . 108.0 ?
C6 C7 O3 . . 112.2(8) ?
C6 C7 C00H . . 109.3(8) ?
O3 C7 C00H . . 101.2(7) ?
C6 C7 C14 . . 112.5(8) ?
O3 C7 C14 . . 103.1(8) ?
C00H C7 C14 . . 117.8(8) ?
O5 C10 O3 . . 123.4(12) ?
O5 C10 C9 . . 126.8(11) ?
O3 C10 C9 . . 109.8(8) ?
O4 C11 C13 . . 108.8(7) ?
O4 C11 C3 . . 109.1(7) ?
C13 C11 C3 . . 111.7(8) ?
O4 C11 C12 . . 104.0(8) ?
C13 C11 C12 . . 111.0(8) ?
C3 C11 C12 . . 111.8(7) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C8 C15 H15A . . 109.5 ?
C8 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C8 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C7 C14 H14A . . 109.5 ?
C7 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C7 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C9 C00H C8 . . 125.1(8) ?
C9 C00H C7 . . 102.4(8) ?
C8 C00H C7 . . 117.5(7) ?
C9 C00H H00H . . 103.0 ?
C8 C00H H00H . . 103.0 ?
C7 C00H H00H . . 103.0 ?
O2 C9 C00H . . 115.7(8) ?
O2 C9 C10 . . 107.7(7) ?
C00H C9 C10 . . 100.9(8) ?
O2 C9 H9 . . 110.7 ?
C00H C9 H9 . . 110.7 ?
C10 C9 H9 . . 110.7 ?
C1 C8 C00H . . 113.3(6) ?
C1 C8 C15 . . 110.3(7) ?
C00H C8 C15 . . 112.3(8) ?
C1 C8 C4 . . 105.9(7) ?
C00H C8 C4 . . 102.7(6) ?
C15 C8 C4 . . 111.9(7) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 C2 C1 C8 . . . . -49.8(11) ?
C4 O1 C3 C11 . . . . 174.9(7) ?
C4 O1 C3 C2 . . . . -58.2(8) ?
C1 C2 C3 O1 . . . . 50.3(9) ?
C1 C2 C3 C11 . . . . 172.9(7) ?
C3 O1 C4 C5 . . . . -166.5(6) ?
C3 O1 C4 C8 . . . . 65.2(8) ?
O1 C4 C5 C6 . . . . 177.8(6) ?
C8 C4 C5 C6 . . . . -57.0(8) ?
C4 C5 C6 C7 . . . . 54.6(8) ?
C5 C6 C7 O3 . . . . -166.0(7) ?
C5 C6 C7 C00H . . . . -54.6(8) ?
C5 C6 C7 C14 . . . . 78.2(10) ?
C10 O3 C7 C6 . . . . 145.3(8) ?
C10 O3 C7 C00H . . . . 28.9(9) ?
C10 O3 C7 C14 . . . . -93.4(9) ?
C7 O3 C10 O5 . . . . 172.7(12) ?
C7 O3 C10 C9 . . . . -6.6(10) ?
O1 C3 C11 O4 . . . . 175.8(7) ?
C2 C3 C11 O4 . . . . 50.3(10) ?
O1 C3 C11 C13 . . . . 55.4(10) ?
C2 C3 C11 C13 . . . . -70.1(10) ?
O1 C3 C11 C12 . . . . -69.7(9) ?
C2 C3 C11 C12 . . . . 164.8(8) ?
C6 C7 C00H C9 . . . . -158.4(7) ?
O3 C7 C00H C9 . . . . -39.9(8) ?
C14 C7 C00H C9 . . . . 71.6(9) ?
C6 C7 C00H C8 . . . . 60.6(9) ?
O3 C7 C00H C8 . . . . 179.1(7) ?
C14 C7 C00H C8 . . . . -69.4(11) ?
C8 C00H C9 O2 . . . . -71.7(10) ?
C7 C00H C9 O2 . . . . 151.2(7) ?
C8 C00H C9 C10 . . . . 172.5(8) ?
C7 C00H C9 C10 . . . . 35.4(8) ?
O5 C10 C9 O2 . . . . 40.0(15) ?
O3 C10 C9 O2 . . . . -140.7(8) ?
O5 C10 C9 C00H . . . . 161.6(12) ?
O3 C10 C9 C00H . . . . -19.1(10) ?
C2 C1 C8 C00H . . . . 165.9(8) ?
C2 C1 C8 C15 . . . . -67.2(10) ?
C2 C1 C8 C4 . . . . 54.0(9) ?
C9 C00H C8 C1 . . . . 58.4(11) ?
C7 C00H C8 C1 . . . . -170.2(7) ?
C9 C00H C8 C15 . . . . -67.4(11) ?
C7 C00H C8 C15 . . . . 64.0(10) ?
C9 C00H C8 C4 . . . . 172.2(7) ?
C7 C00H C8 C4 . . . . -56.4(9) ?
O1 C4 C8 C1 . . . . -61.5(7) ?
C5 C4 C8 C1 . . . . 174.9(6) ?
O1 C4 C8 C00H . . . . 179.5(6) ?
C5 C4 C8 C00H . . . . 55.9(8) ?
O1 C4 C8 C15 . . . . 58.8(10) ?
C5 C4 C8 C15 . . . . -64.8(9) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O2 2_656 0.84 2.41 2.777(15) 107.0 ?
O4 H4A O6 . 0.84 1.99 2.676(11) 138.0 ?
C5 H5A O3 4_646 0.99 2.49 3.447(11) 161.9 ?
C12 H12A O5 1_546 0.98 2.54 3.417(13) 149.7 ?

