# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_cu_20240326_YKD_A31_0m_5
_database_code_depnum_ccdc_archive 'CCDC 2375874'
loop_
_audit_author_name
_audit_author_address
fanshiying
;China Pharmaceutical University
China
;
_audit_update_record             
;
2024-08-06 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V118 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C36 H38 O11'
_chemical_formula_moiety         ?
_chemical_formula_weight         646.66
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1942(6)
_cell_length_b                   18.9173(8)
_cell_length_c                   13.9396(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.265(4)
_cell_angle_gamma                90
_cell_volume                     3202.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4777
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      66.595
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.614592
_exptl_absorpt_correction_T_max  0.752819
_exptl_absorpt_process_details   
;TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1: Krause, L.,
Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.937
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      150(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            5696
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_theta_min         3.640
_diffrn_reflns_theta_max         66.664
_diffrn_reflns_theta_full        66.664
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5696
_reflns_number_gt                4471
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       
'Bruker BIS 8.5.0.27 Release/2023-03-20 && APEX5 2023.9-2'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0711P)²+5.0058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5696
_refine_ls_number_parameters     514
_refine_ls_number_restraints     625
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1957
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_twin_special_details            
'The data was integrated as a 2-component twin.'
_twin_individual_id              2
_twin_individual_twin_matrix_11  -0.00157
_twin_individual_twin_matrix_12  0.16174
_twin_individual_twin_matrix_13  0.99987
_twin_individual_twin_matrix_21  -1.0
_twin_individual_twin_matrix_22  -0.00065
_twin_individual_twin_matrix_23  -0.00376
_twin_individual_twin_matrix_31  0.00019
_twin_individual_twin_matrix_32  -0.99987
_twin_individual_twin_matrix_33  0.00161

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'

_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_
_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
C1 C 0.5700(3) 0.5701(2) 0.5898(3) 0.0393(9) Uani 1 1 d . U . . .
C2 C 0.6140(3) 0.5127(2) 0.6417(3) 0.0448(10) Uani 1 1 d . U . . .
C3 C 0.7517(3) 0.5828(3) 0.6106(4) 0.0521(11) Uani 1 1 d . U . . .
H3A H 0.811788 0.579793 0.567526 0.063 Uiso 1 1 calc R U . . .
H3B H 0.775974 0.614218 0.665278 0.063 Uiso 1 1 calc R U . . .
C4 C 0.4587(3) 0.5813(2) 0.5736(3) 0.0358(8) Uani 1 1 d . U . . .
H4 H 0.429321 0.621119 0.538562 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3906(3) 0.5305(2) 0.6118(3) 0.0356(8) Uani 1 1 d . U . . .
C6 C 0.4357(4) 0.4733(2) 0.6641(3) 0.0465(10) Uani 1 1 d . U . . .
H6 H 0.387943 0.439516 0.688865 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5492(4) 0.4642(2) 0.6811(4) 0.0520(11) Uani 1 1 d . U . . .
H7 H 0.579954 0.425898 0.718483 0.062 Uiso 1 1 calc R U . . .
C8 C 0.2684(3) 0.5333(2) 0.5949(3) 0.0383(9) Uani 1 1 d . U . . .
C9 C 0.2120(3) 0.6005(2) 0.5557(3) 0.0333(8) Uani 1 1 d . U . . .
H9 H 0.259487 0.624599 0.510888 0.040 Uiso 1 1 calc R U . . .
C10 C 0.0996(3) 0.5849(2) 0.5034(3) 0.0397(9) Uani 1 1 d . U . . .
H10A H 0.085049 0.617062 0.447670 0.048 Uiso 1 1 calc R U . . .
H10B H 0.096719 0.535574 0.479609 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1808(3) 0.65368(19) 0.6344(3) 0.0296(8) Uani 1 1 d . U . . .
C13 C 0.0149(4) 0.5175(3) 0.7363(4) 0.0585(13) Uani 1 1 d . U . . .
H13A H 0.037260 0.488298 0.792794 0.088 Uiso 1 1 calc R U . . .
H13B H 0.011758 0.488277 0.678112 0.088 Uiso 1 1 calc R U . . .
H13C H -0.057895 0.537897 0.742979 0.088 Uiso 1 1 calc R U . . .
C20 C 0.2496(3) 0.7669(2) 0.6060(3) 0.0327(8) Uani 1 1 d . U . . .
C21 C 0.2952(3) 0.7483(2) 0.7097(3) 0.0320(8) Uani 1 1 d . U . . .
C22 C 0.2665(3) 0.6699(2) 0.7197(3) 0.0325(8) Uani 1 1 d . U . . .
H22A H 0.235419 0.660930 0.781680 0.039 Uiso 1 1 calc R U . . .
H22B H 0.332905 0.640108 0.716540 0.039 Uiso 1 1 calc R U . . .
C24 C 0.2018(3) 0.8424(2) 0.6082(3) 0.0375(9) Uani 1 1 d . U . . .
C25 C 0.2253(3) 0.7949(2) 0.7698(3) 0.0353(8) Uani 1 1 d . U . . .
C26 C 0.1566(4) 0.8466(2) 0.7075(3) 0.0411(9) Uani 1 1 d . U . . .
H26A H 0.164575 0.895016 0.734072 0.049 Uiso 1 1 calc R U . . .
H26B H 0.077874 0.833134 0.702877 0.049 Uiso 1 1 calc R U . . .
C27 C 0.1233(4) 0.8605(2) 0.5231(3) 0.0457(10) Uani 1 1 d . U . . .
H27 H 0.055090 0.837403 0.506139 0.055 Uiso 1 1 calc R U . . .
C28 C 0.1634(4) 0.9138(2) 0.4746(3) 0.0539(12) Uani 1 1 d . U . . .
H28 H 0.128610 0.932712 0.416394 0.065 Uiso 1 1 calc R U . . .
C29 C 0.2696(5) 0.9402(2) 0.5230(3) 0.0545(12) Uani 1 1 d . U . . .
C30 C 0.4195(3) 0.7662(2) 0.7291(3) 0.0341(8) Uani 1 1 d . U . . .
H30A H 0.461409 0.735629 0.687970 0.041 Uiso 1 1 calc R U . . .
H30B H 0.430956 0.815832 0.709708 0.041 Uiso 1 1 calc R U . . .
C31 C 0.4656(3) 0.7572(2) 0.8324(3) 0.0393(9) Uani 1 1 d . U . . .
H31 H 0.433791 0.785262 0.879018 0.047 Uiso 1 1 calc R U . . .
C32 C 0.5460(4) 0.7140(2) 0.8645(3) 0.0462(10) Uani 1 1 d . U . . .
C33 C 0.5851(4) 0.7102(3) 0.9712(4) 0.0623(13) Uani 1 1 d . U . . .
H33A H 0.582092 0.661060 0.993171 0.093 Uiso 1 1 calc R U . . .
H33B H 0.537313 0.739484 1.007785 0.093 Uiso 1 1 calc R U . . .
H33C H 0.660968 0.727517 0.981465 0.093 Uiso 1 1 calc R U . . .
C34 C 0.3636(5) 0.9329(3) 0.4591(4) 0.0714(16) Uani 1 1 d . U . . .
H34A H 0.347382 0.961067 0.400521 0.107 Uiso 1 1 calc R U . . .
H34B H 0.372110 0.883175 0.441781 0.107 Uiso 1 1 calc R U . . .
H34C H 0.431999 0.949935 0.494025 0.107 Uiso 1 1 calc R U . . .
C35 C 0.2621(6) 1.0145(3) 0.5618(5) 0.0805(19) Uani 1 1 d . U . . .
H35A H 0.249780 1.047818 0.508047 0.121 Uiso 1 1 calc R U . . .
H35B H 0.330928 1.026480 0.600263 0.121 Uiso 1 1 calc R U . . .
H35C H 0.200680 1.017454 0.602354 0.121 Uiso 1 1 calc R U . . .
C36 C 0.6068(5) 0.6662(3) 0.8018(4) 0.0692(15) Uani 1 1 d . U . . .
H36A H 0.684618 0.664179 0.826542 0.104 Uiso 1 1 calc R U . . .
H36B H 0.600555 0.684525 0.735797 0.104 Uiso 1 1 calc R U . . .
H36C H 0.574995 0.618634 0.802218 0.104 Uiso 1 1 calc R U . . .
O1 O 0.7268(2) 0.51461(17) 0.6448(3) 0.0582(9) Uani 1 1 d . U . . .
O2 O 0.6534(2) 0.61055(16) 0.5587(2) 0.0500(8) Uani 1 1 d . U . . .
O3 O 0.0189(2) 0.59557(15) 0.57160(19) 0.0389(6) Uani 1 1 d . U . . .
O4 O 0.2132(3) 0.48072(16) 0.6079(3) 0.0605(9) Uani 1 1 d . U . . .
O5 O 0.0919(2) 0.57225(14) 0.72926(19) 0.0402(6) Uani 1 1 d . U . . .
O6 O 0.1578(2) 0.72083(13) 0.58752(18) 0.0323(6) Uani 1 1 d . U . . .
O9 O 0.3272(2) 0.75606(16) 0.54012(19) 0.0381(6) Uani 1 1 d . U . . .
H9A H 0.295437 0.755385 0.484033 0.057 Uiso 1 1 calc R U . . .
O10 O 0.2899(3) 0.89323(15) 0.6049(2) 0.0462(7) Uani 1 1 d . U . . .
O11 O 0.2222(2) 0.78917(15) 0.85653(19) 0.0423(7) Uani 1 1 d . U . . .
C11 C 0.0669(3) 0.6247(2) 0.6583(3) 0.0338(8) Uani 1 1 d D U . . .
C14 C -0.0138(10) 0.6802(6) 0.6887(5) 0.0360(11) Uani 0.824(5) 1 d D U P A 1
C15 C -0.0695(8) 0.7222(5) 0.6194(4) 0.0409(12) Uani 0.824(5) 1 d D U P A 1
H15 H -0.057210 0.715489 0.553703 0.049 Uiso 0.824(5) 1 calc R U P A 1
C16 C -0.1438(5) 0.7744(3) 0.6435(4) 0.0461(12) Uani 0.824(5) 1 d D U P A 1
H16 H -0.182649 0.802786 0.595499 0.055 Uiso 0.824(5) 1 calc R U P A 1
C17 C -0.1579(5) 0.7825(3) 0.7384(4) 0.0480(12) Uani 0.824(5) 1 d D U P A 1
C18 C -0.1042(5) 0.7411(3) 0.8070(4) 0.0461(12) Uani 0.824(5) 1 d D U P A 1
C19 C -0.0314(5) 0.6887(4) 0.7860(4) 0.0421(13) Uani 0.824(5) 1 d D U P A 1
H19 H 0.004853 0.659874 0.834952 0.051 Uiso 0.824(5) 1 calc R U P A 1
C23 C -0.1934(6) 0.8234(3) 0.8808(5) 0.0621(15) Uani 0.824(5) 1 d D U P A 1
H23A H -0.257269 0.826418 0.919595 0.075 Uiso 0.824(5) 1 calc R U P A 1
H23B H -0.142350 0.862685 0.899721 0.075 Uiso 0.824(5) 1 calc R U P A 1
O7 O -0.2293(3) 0.8278(2) 0.7807(4) 0.0553(11) Uani 0.824(5) 1 d D U P A 1
O8 O -0.1383(3) 0.7565(2) 0.8967(3) 0.0600(11) Uani 0.824(5) 1 d D U P A 1
C14A C -0.009(5) 0.677(3) 0.7023(14) 0.039(3) Uani 0.176(5) 1 d D U P A 2
C15A C -0.001(2) 0.6861(17) 0.8010(14) 0.042(3) Uani 0.176(5) 1 d D U P A 2
H15A H 0.054162 0.661791 0.840401 0.051 Uiso 0.176(5) 1 calc R U P A 2
C16A C -0.075(2) 0.7308(13) 0.8435(11) 0.052(2) Uani 0.176(5) 1 d D U P A 2
H16A H -0.083894 0.728189 0.910335 0.062 Uiso 0.176(5) 1 calc R U P A 2
C17A C -0.132(2) 0.7779(13) 0.7850(10) 0.053(2) Uani 0.176(5) 1 d D U P A 2
C18A C -0.134(2) 0.7724(12) 0.6883(11) 0.045(2) Uani 0.176(5) 1 d D U P A 2
C19A C -0.074(4) 0.723(2) 0.6423(13) 0.041(3) Uani 0.176(5) 1 d D U P A 2
H19A H -0.076584 0.720219 0.574075 0.049 Uiso 0.176(5) 1 calc R U P A 2
C23A C -0.2532(18) 0.8552(13) 0.7206(13) 0.057(3) Uani 0.176(5) 1 d D U P A 2
H23C H -0.258097 0.907204 0.714083 0.068 Uiso 0.176(5) 1 calc R U P A 2
H23D H -0.328799 0.835792 0.718524 0.068 Uiso 0.176(5) 1 calc R U P A 2
O7A O -0.1923(19) 0.8367(11) 0.8090(12) 0.059(3) Uani 0.176(5) 1 d D U P A 2
O8A O -0.1966(13) 0.8258(8) 0.6441(10) 0.053(2) Uani 0.176(5) 1 d D U P A 2


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.371(5) . ?
C1 O2 1.374(5) . ?
C1 C2 1.386(6) . ?
C2 C7 1.359(7) . ?
C2 O1 1.372(5) . ?
C3 O1 1.419(6) . ?
C3 O2 1.441(5) . ?
C4 C5 1.407(5) . ?
C5 C6 1.389(6) . ?
C5 C8 1.488(5) . ?
C6 C7 1.394(6) . ?
C8 O4 1.223(5) . ?
C8 C9 1.523(5) . ?
C9 C10 1.521(5) . ?
C9 C12 1.561(5) . ?
C10 O3 1.444(5) . ?
C12 O6 1.444(4) . ?
C12 C22 1.540(5) . ?
C12 C11 1.558(5) . ?
C13 O5 1.407(5) . ?
C20 O9 1.393(4) . ?
C20 O6 1.423(4) . ?
C20 C21 1.541(5) . ?
C20 C24 1.545(5) . ?
C21 C25 1.527(5) . ?
C21 C22 1.534(5) . ?
C21 C30 1.552(5) . ?
C24 O10 1.446(5) . ?
C24 C27 1.494(5) . ?
C24 C26 1.537(6) . ?
C25 O11 1.218(5) . ?
C25 C26 1.510(5) . ?
C27 C28 1.333(6) . ?
C28 C29 1.490(7) . ?
C29 O10 1.450(5) . ?
C29 C35 1.513(7) . ?
C29 C34 1.521(8) . ?
C30 C31 1.506(5) . ?
C31 C32 1.321(6) . ?
C32 C36 1.501(7) . ?
C32 C33 1.522(6) . ?
O3 C11 1.406(4) . ?
O5 C11 1.414(5) . ?
C11 C14A 1.521(9) . ?
C11 C14 1.526(6) . ?
C14 C15 1.380(8) . ?
C14 C19 1.401(8) . ?
C15 C16 1.401(8) . ?
C16 C17 1.359(8) . ?
C17 C18 1.357(8) . ?
C17 O7 1.390(6) . ?
C18 C19 1.380(8) . ?
C18 O8 1.385(6) . ?
C23 O7 1.426(8) . ?
C23 O8 1.440(7) . ?
C14A C15A 1.380(12) . ?
C14A C19A 1.400(12) . ?
C15A C16A 1.401(11) . ?
C16A C17A 1.358(11) . ?
C17A C18A 1.351(11) . ?
C17A O7A 1.392(10) . ?
C18A C19A 1.379(11) . ?
C18A O8A 1.380(10) . ?
C23A O7A 1.423(12) . ?
C23A O8A 1.435(11) . ?

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
C4 C1 O2 127.7(4) . . ?
C4 C1 C2 122.5(4) . . ?
O2 C1 C2 109.8(3) . . ?
C7 C2 O1 128.5(4) . . ?
C7 C2 C1 121.9(4) . . ?
O1 C2 C1 109.6(4) . . ?
O1 C3 O2 107.8(3) . . ?
C1 C4 C5 116.2(4) . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 C8 116.9(4) . . ?
C4 C5 C8 122.2(4) . . ?
C5 C6 C7 121.6(4) . . ?
C2 C7 C6 117.0(4) . . ?
O4 C8 C5 120.3(4) . . ?
O4 C8 C9 119.7(4) . . ?
C5 C8 C9 119.9(3) . . ?
C10 C9 C8 111.6(3) . . ?
C10 C9 C12 101.2(3) . . ?
C8 C9 C12 114.7(3) . . ?
O3 C10 C9 107.2(3) . . ?
O6 C12 C22 105.3(3) . . ?
O6 C12 C11 105.5(3) . . ?
C22 C12 C11 117.4(3) . . ?
O6 C12 C9 107.4(3) . . ?
C22 C12 C9 118.6(3) . . ?
C11 C12 C9 101.7(3) . . ?
O9 C20 O6 111.2(3) . . ?
O9 C20 C21 112.1(3) . . ?
O6 C20 C21 104.0(3) . . ?
O9 C20 C24 115.4(3) . . ?
O6 C20 C24 106.1(3) . . ?
C21 C20 C24 107.2(3) . . ?
C25 C21 C22 111.4(3) . . ?
C25 C21 C20 102.2(3) . . ?
C22 C21 C20 103.8(3) . . ?
C25 C21 C30 111.3(3) . . ?
C22 C21 C30 115.0(3) . . ?
C20 C21 C30 112.1(3) . . ?
C21 C22 C12 105.5(3) . . ?
O10 C24 C27 104.2(3) . . ?
O10 C24 C26 108.9(3) . . ?
C27 C24 C26 116.5(4) . . ?
O10 C24 C20 109.4(3) . . ?
C27 C24 C20 114.3(3) . . ?
C26 C24 C20 103.4(3) . . ?
O11 C25 C26 124.2(4) . . ?
O11 C25 C21 124.3(4) . . ?
C26 C25 C21 111.5(3) . . ?
C25 C26 C24 105.0(3) . . ?
C28 C27 C24 109.8(4) . . ?
C27 C28 C29 111.6(4) . . ?
O10 C29 C28 103.3(3) . . ?
O10 C29 C35 107.4(4) . . ?
C28 C29 C35 113.2(5) . . ?
O10 C29 C34 108.8(4) . . ?
C28 C29 C34 112.1(4) . . ?
C35 C29 C34 111.5(5) . . ?
C31 C30 C21 114.5(3) . . ?
C32 C31 C30 126.5(4) . . ?
C31 C32 C36 124.5(4) . . ?
C31 C32 C33 121.2(4) . . ?
C36 C32 C33 114.4(4) . . ?
C2 O1 C3 105.0(3) . . ?
C1 O2 C3 104.2(3) . . ?
C11 O3 C10 111.4(3) . . ?
C13 O5 C11 117.6(3) . . ?
C20 O6 C12 109.9(3) . . ?
C24 O10 C29 111.0(3) . . ?
O3 C11 O5 111.9(3) . . ?
O3 C11 C14A 112(2) . . ?
O5 C11 C14A 105.9(15) . . ?
O3 C11 C14 106.3(5) . . ?
O5 C11 C14 113.0(4) . . ?
O3 C11 C12 105.3(3) . . ?
O5 C11 C12 104.9(3) . . ?
C14A C11 C12 116(3) . . ?
C14 C11 C12 115.3(7) . . ?
C15 C14 C19 120.2(4) . . ?
C15 C14 C11 119.3(5) . . ?
C19 C14 C11 120.5(5) . . ?
C14 C15 C16 121.7(5) . . ?
C17 C16 C15 117.1(5) . . ?
C18 C17 C16 121.6(5) . . ?
C18 C17 O7 109.8(5) . . ?
C16 C17 O7 128.5(5) . . ?
C17 C18 C19 123.0(5) . . ?
C17 C18 O8 110.4(4) . . ?
C19 C18 O8 126.5(5) . . ?
C18 C19 C14 116.5(5) . . ?
O7 C23 O8 107.4(4) . . ?
C17 O7 C23 103.3(4) . . ?
C18 O8 C23 102.7(4) . . ?
C15A C14A C19A 120.0(11) . . ?
C15A C14A C11 119.7(13) . . ?
C19A C14A C11 119.6(13) . . ?
C14A C15A C16A 120.6(12) . . ?
C17A C16A C15A 117.1(12) . . ?
C18A C17A C16A 120.5(10) . . ?
C18A C17A O7A 110.0(9) . . ?
C16A C17A O7A 129.5(11) . . ?
C17A C18A C19A 123.8(11) . . ?
C17A C18A O8A 110.2(8) . . ?
C19A C18A O8A 125.8(11) . . ?
C18A C19A C14A 115.9(11) . . ?
O7A C23A O8A 107.5(10) . . ?
C17A O7A C23A 103.5(9) . . ?
C18A O8A C23A 103.7(9) . . ?

####################################################################### 
# 
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 2375875'
loop_
_audit_author_name
_audit_author_address
fanshiying
;China Pharmaceutical University
China
;
_audit_update_record             
;
2024-08-06 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H36 O11, C H4 O'
_chemical_formula_sum            'C36 H40 O12'
_chemical_formula_weight         664.68
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5584(5)
_cell_length_b                   11.0468(7)
_cell_length_c                   29.2690(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3413.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5467
_cell_measurement_temperature    233.00
_cell_measurement_theta_max      63.350
_cell_measurement_theta_min      3.019
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  0.3825
_exptl_absorpt_correction_T_min  0.2727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1088 before and 0.0840 after correction.
The Ratio of minimum to maximum transmission is 0.7129.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            53410
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.949
_diffrn_reflns_theta_min         4.278
_diffrn_ambient_temperature      233.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4543
_reflns_number_total             6304
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 1577 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         6304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0728
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1535P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1954
_refine_ls_wR_factor_ref         0.2167
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups, All O(H) groups
2.a Everything fixed:
 H7, H12
2.b Ternary CH refined with riding coordinates:
 C10(H10)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C19(H19A,H19B), C20(H20A,H20B), C29(H29A,H29B),
 C31(H31A,H31B)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5A), C7(H7A), C14(H14), C15(H15), C18(H18), C24(H24), C25(H25),
 C32(H32)
2.e Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C), C36(H36A,H36B,H36C)
2.f Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 -0.0453(4) 0.8206(5) 0.3368(2) 0.0974(15) Uani 1 1 d . . . . .
O2 O -0.0789(4) 0.6680(5) 0.28460(19) 0.0867(13) Uani 1 1 d . . . . .
O3 O 0.3400(4) 0.4481(4) 0.26077(15) 0.0748(11) Uani 1 1 d . . . . .
O4 O 0.6738(4) 0.4724(4) 0.25628(14) 0.0717(10) Uani 1 1 d . . . . .
O5 O 0.5462(4) 0.3033(4) 0.26678(15) 0.0717(10) Uani 1 1 d . . . . .
H5 H 0.483202 0.341621 0.257913 0.108 Uiso 1 1 calc R U . . .
O6 O 0.6654(3) 0.5098(3) 0.35282(12) 0.0598(8) Uani 1 1 d . . . . .
O7 O 0.5537(4) 0.6263(4) 0.40617(15) 0.0719(10) Uani 1 1 d . . . . .
H7 H 0.551080 0.646780 0.433580 0.108 Uiso 1 1 d . U . . .
O8 O 1.0930(4) 0.3101(5) 0.3144(2) 0.0937(15) Uani 1 1 d . . . . .
O9 O 1.0608(4) 0.1168(5) 0.34251(19) 0.0913(14) Uani 1 1 d . . . . .
O10 O 0.6130(4) 0.2077(4) 0.42529(17) 0.0811(12) Uani 1 1 d . . . . .
O11 O 0.7146(4) 0.5371(4) 0.47552(14) 0.0758(11) Uani 1 1 d . . . . .
C1 C 1.1520(7) 0.1986(8) 0.3259(3) 0.097(2) Uani 1 1 d . . . . .
H1A H 1.193412 0.164498 0.298888 0.117 Uiso 1 1 calc R U . . .
H1B H 1.216779 0.212474 0.349317 0.117 Uiso 1 1 calc R U . . .
C2 C 0.9651(5) 0.2832(6) 0.3143(2) 0.0722(15) Uani 1 1 d . . . . .
C3 C 0.9467(6) 0.1699(6) 0.3300(2) 0.0727(15) Uani 1 1 d . . . . .
C4 C 0.8273(6) 0.1201(6) 0.3332(2) 0.0745(16) Uani 1 1 d . . . . .
H4 H 0.813742 0.041703 0.344716 0.089 Uiso 1 1 calc R U . . .
C5 C 0.7284(5) 0.1930(6) 0.3184(2) 0.0675(14) Uani 1 1 d . . . . .
H5A H 0.645677 0.161627 0.319512 0.081 Uiso 1 1 calc R U . . .
C6 C 0.7452(5) 0.3075(5) 0.3025(2) 0.0623(13) Uani 1 1 d . . . . .
C7 C 0.8684(5) 0.3578(6) 0.3001(2) 0.0697(14) Uani 1 1 d . . . . .
H7A H 0.883199 0.436901 0.289568 0.084 Uiso 1 1 calc R U . . .
C8 C 0.6321(5) 0.3827(5) 0.28704(18) 0.0595(12) Uani 1 1 d . . . . .
C9 C 0.5658(4) 0.4559(5) 0.32555(18) 0.0574(12) Uani 1 1 d . . . . .
C10 C 0.5015(5) 0.5601(5) 0.29798(19) 0.0613(12) Uani 1 1 d . . . . .
H10 H 0.506476 0.636276 0.315709 0.074 Uiso 1 1 calc R U . . .
C11 C 0.5870(5) 0.5700(6) 0.2554(2) 0.0693(14) Uani 1 1 d . . . . .
H11A H 0.535541 0.566327 0.227559 0.083 Uiso 1 1 calc R U . . .
H11B H 0.632832 0.647122 0.255649 0.083 Uiso 1 1 calc R U . . .
C12 C 0.3634(5) 0.5345(5) 0.28560(18) 0.0577(11) Uani 1 1 d . . . . .
C13 C 0.2609(5) 0.6130(5) 0.30250(19) 0.0612(12) Uani 1 1 d . . . . .
C14 C 0.2775(6) 0.7038(7) 0.3340(3) 0.0826(19) Uani 1 1 d . . . . .
H14 H 0.358308 0.714848 0.346786 0.099 Uiso 1 1 calc R U . . .
C15 C 0.1807(6) 0.7793(9) 0.3477(3) 0.107(3) Uani 1 1 d . . . . .
H15 H 0.194009 0.841494 0.369096 0.128 Uiso 1 1 calc R U . . .
C16 C 0.0635(6) 0.7591(6) 0.3284(3) 0.0793(17) Uani 1 1 d . . . . .
C17 C 0.0458(5) 0.6676(5) 0.2980(2) 0.0641(13) Uani 1 1 d . . . . .
C18 C 0.1395(5) 0.5920(5) 0.2843(2) 0.0632(12) Uani 1 1 d . . . . .
H18 H 0.124147 0.528679 0.263590 0.076 Uiso 1 1 calc R U . . .
C19 C -0.1381(7) 0.7678(7) 0.3065(3) 0.0858(19) Uani 1 1 d . . . . .
H19A H -0.212225 0.740610 0.323860 0.103 Uiso 1 1 calc R U . . .
H19B H -0.165847 0.827427 0.283828 0.103 Uiso 1 1 calc R U . . .
C20 C 0.4812(5) 0.3857(5) 0.35941(19) 0.0607(12) Uani 1 1 d . . . . .
H20A H 0.393695 0.415158 0.358160 0.073 Uiso 1 1 calc R U . . .
H20B H 0.481787 0.298903 0.352493 0.073 Uiso 1 1 calc R U . . .
C21 C 0.5400(5) 0.4103(5) 0.40666(19) 0.0631(13) Uani 1 1 d . . . . .
C22 C 0.6214(5) 0.5212(5) 0.39974(19) 0.0613(12) Uani 1 1 d . . . . .
C23 C 0.7412(5) 0.5033(6) 0.42886(19) 0.0654(13) Uani 1 1 d . . . . .
C24 C 0.8498(5) 0.5880(6) 0.4153(2) 0.0710(15) Uani 1 1 d . . . . .
H24 H 0.889719 0.590279 0.386655 0.085 Uiso 1 1 calc R U . . .
C25 C 0.8780(6) 0.6574(7) 0.4507(3) 0.0851(18) Uani 1 1 d . . . . .
H25 H 0.940287 0.718116 0.449864 0.102 Uiso 1 1 calc R U . . .
C26 C 0.8009(6) 0.6295(7) 0.4922(2) 0.0793(17) Uani 1 1 d . . . . .
C27 C 0.8806(8) 0.5769(11) 0.5306(3) 0.117(3) Uani 1 1 d . . . . .
H27A H 0.825543 0.549205 0.555002 0.176 Uiso 1 1 calc R U . . .
H27B H 0.937436 0.638560 0.542264 0.176 Uiso 1 1 calc R U . . .
H27C H 0.929692 0.509183 0.519097 0.176 Uiso 1 1 calc R U . . .
C28 C 0.7222(10) 0.7351(9) 0.5094(4) 0.114(3) Uani 1 1 d . . . . .
H28A H 0.671866 0.767367 0.484488 0.170 Uiso 1 1 calc R U . . .
H28B H 0.777849 0.797763 0.521034 0.170 Uiso 1 1 calc R U . . .
H28C H 0.666605 0.707535 0.533634 0.170 Uiso 1 1 calc R U . . .
C29 C 0.7644(5) 0.3695(6) 0.4267(2) 0.0696(14) Uani 1 1 d . . . . .
H29A H 0.803690 0.340862 0.455084 0.083 Uiso 1 1 calc R U . . .
H29B H 0.820165 0.349458 0.401070 0.083 Uiso 1 1 calc R U . . .
C30 C 0.6354(5) 0.3127(6) 0.4203(2) 0.0656(13) Uani 1 1 d . . . . .
C31 C 0.4402(5) 0.4236(7) 0.4455(2) 0.0759(16) Uani 1 1 d . . . . .
H31A H 0.485370 0.429492 0.474669 0.091 Uiso 1 1 calc R U . . .
H31B H 0.394828 0.500018 0.440952 0.091 Uiso 1 1 calc R U . . .
C32 C 0.3462(5) 0.3256(7) 0.4491(2) 0.0759(16) Uani 1 1 d . . . . .
H32 H 0.377418 0.248245 0.456419 0.091 Uiso 1 1 calc R U . . .
C33 C 0.2218(6) 0.3352(8) 0.4432(2) 0.0825(18) Uani 1 1 d . . . . .
C34 C 0.1575(7) 0.4504(10) 0.4287(3) 0.111(3) Uani 1 1 d . . . . .
H34A H 0.108813 0.482552 0.453999 0.167 Uiso 1 1 calc R U . . .
H34B H 0.101459 0.433779 0.403176 0.167 Uiso 1 1 calc R U . . .
H34C H 0.220901 0.509073 0.419449 0.167 Uiso 1 1 calc R U . . .
C35 C 0.1350(8) 0.2294(9) 0.4517(3) 0.103(2) Uani 1 1 d . . . . .
H35A H 0.185162 0.157259 0.457139 0.154 Uiso 1 1 calc R U . . .
H35B H 0.081503 0.216908 0.425143 0.154 Uiso 1 1 calc R U . . .
H35C H 0.082578 0.245855 0.478146 0.154 Uiso 1 1 calc R U . . .
O12 O 0.6449(7) 0.8441(5) 0.3833(2) 0.1146(19) Uani 1 1 d . . . . .
C36 C 0.5582(11) 0.9147(9) 0.3604(4) 0.127(3) Uani 1 1 d . . . . .
H36A H 0.593583 0.939717 0.331319 0.190 Uiso 1 1 calc R U . . .
H36B H 0.538533 0.985698 0.378577 0.190 Uiso 1 1 calc R U . . .
H36C H 0.481511 0.868420 0.355200 0.190 Uiso 1 1 calc R U . . .
H12 H 0.662390 0.772820 0.396260 0.190 Uiso 1 1 d . 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 C16 1.357(7) . ?
O1 C19 1.445(9) . ?
O2 C17 1.374(6) . ?
O2 C19 1.421(9) . ?
O3 C12 1.224(7) . ?
O4 C8 1.409(7) . ?
O4 C11 1.415(7) . ?
O5 H5 0.8300 . ?
O5 C8 1.394(7) . ?
O6 C9 1.448(6) . ?
O6 C22 1.455(7) . ?
O7 H7 0.8340 . ?
O7 C22 1.377(6) . ?
O8 C1 1.420(10) . ?
O8 C2 1.383(7) . ?
O9 C1 1.407(10) . ?
O9 C3 1.389(7) . ?
O10 C30 1.193(7) . ?
O11 C23 1.444(7) . ?
O11 C26 1.453(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C3 1.347(10) . ?
C2 C7 1.376(9) . ?
C3 C4 1.379(9) . ?
C4 H4 0.9400 . ?
C4 C5 1.388(9) . ?
C5 H5A 0.9400 . ?
C5 C6 1.360(9) . ?
C6 C7 1.417(8) . ?
C6 C8 1.524(8) . ?
C7 H7A 0.9400 . ?
C8 C9 1.553(8) . ?
C9 C10 1.562(8) . ?
C9 C20 1.543(8) . ?
C10 H10 0.9900 . ?
C10 C11 1.543(8) . ?
C10 C12 1.529(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.472(7) . ?
C13 C14 1.374(9) . ?
C13 C18 1.407(8) . ?
C14 H14 0.9400 . ?
C14 C15 1.379(10) . ?
C15 H15 0.9400 . ?
C15 C16 1.378(10) . ?
C16 C17 1.359(9) . ?
C17 C18 1.356(8) . ?
C18 H18 0.9400 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 C21 1.540(8) . ?
C21 C22 1.510(8) . ?
C21 C30 1.529(8) . ?
C21 C31 1.557(8) . ?
C22 C23 1.538(7) . ?
C23 C24 1.531(8) . ?
C23 C29 1.499(9) . ?
C24 H24 0.9400 . ?
C24 C25 1.322(10) . ?
C25 H25 0.9400 . ?
C25 C26 1.493(11) . ?
C26 C27 1.520(11) . ?
C26 C28 1.518(11) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 C30 1.511(8) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 C32 1.473(10) . ?
C32 H32 0.9400 . ?
C32 C33 1.330(9) . ?
C33 C34 1.503(12) . ?
C33 C35 1.506(11) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 H34C 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 H35C 0.9700 . ?
O12 C36 1.376(12) . ?
O12 H12 0.8934 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 H36C 0.9700 . ?

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
C16 O1 C19 105.2(5) . . ?
C17 O2 C19 107.1(5) . . ?
C8 O4 C11 110.2(4) . . ?
C8 O5 H5 109.5 . . ?
C9 O6 C22 108.9(4) . . ?
C22 O7 H7 112.2 . . ?
C2 O8 C1 104.0(6) . . ?
C3 O9 C1 103.4(5) . . ?
C23 O11 C26 112.1(5) . . ?
O8 C1 H1A 109.7 . . ?
O8 C1 H1B 109.7 . . ?
O9 C1 O8 109.8(6) . . ?
O9 C1 H1A 109.7 . . ?
O9 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 O8 109.9(5) . . ?
C3 C2 C7 123.5(6) . . ?
C7 C2 O8 126.6(6) . . ?
C2 C3 O9 110.9(6) . . ?
C2 C3 C4 121.7(6) . . ?
C4 C3 O9 127.3(6) . . ?
C3 C4 H4 122.1 . . ?
C3 C4 C5 115.8(6) . . ?
C5 C4 H4 122.1 . . ?
C4 C5 H5A 118.4 . . ?
C6 C5 C4 123.3(5) . . ?
C6 C5 H5A 118.4 . . ?
C5 C6 C7 120.1(5) . . ?
C5 C6 C8 120.5(5) . . ?
C7 C6 C8 119.4(5) . . ?
C2 C7 C6 115.6(5) . . ?
C2 C7 H7A 122.2 . . ?
C6 C7 H7A 122.2 . . ?
O4 C8 C6 109.1(4) . . ?
O4 C8 C9 103.8(4) . . ?
O5 C8 O4 112.0(4) . . ?
O5 C8 C6 107.0(4) . . ?
O5 C8 C9 110.1(4) . . ?
C6 C8 C9 114.9(4) . . ?
O6 C9 C8 106.7(4) . . ?
O6 C9 C10 107.3(4) . . ?
O6 C9 C20 105.9(4) . . ?
C8 C9 C10 101.8(4) . . ?
C20 C9 C8 117.7(4) . . ?
C20 C9 C10 116.8(4) . . ?
C9 C10 H10 109.4 . . ?
C11 C10 C9 102.4(4) . . ?
C11 C10 H10 109.4 . . ?
C12 C10 C9 113.6(4) . . ?
C12 C10 H10 109.4 . . ?
C12 C10 C11 112.3(5) . . ?
O4 C11 C10 108.1(5) . . ?
O4 C11 H11A 110.1 . . ?
O4 C11 H11B 110.1 . . ?
C10 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
O3 C12 C10 118.5(5) . . ?
O3 C12 C13 120.7(5) . . ?
C13 C12 C10 120.8(5) . . ?
C14 C13 C12 124.2(5) . . ?
C14 C13 C18 119.4(5) . . ?
C18 C13 C12 116.5(5) . . ?
C13 C14 H14 118.6 . . ?
C13 C14 C15 122.9(6) . . ?
C15 C14 H14 118.6 . . ?
C14 C15 H15 121.7 . . ?
C16 C15 C14 116.6(6) . . ?
C16 C15 H15 121.7 . . ?
O1 C16 C15 127.2(6) . . ?
O1 C16 C17 111.9(6) . . ?
C17 C16 C15 120.8(6) . . ?
C16 C17 O2 108.5(5) . . ?
C18 C17 O2 128.0(6) . . ?
C18 C17 C16 123.4(5) . . ?
C13 C18 H18 121.6 . . ?
C17 C18 C13 116.8(5) . . ?
C17 C18 H18 121.6 . . ?
O1 C19 H19A 110.3 . . ?
O1 C19 H19B 110.3 . . ?
O2 C19 O1 107.0(5) . . ?
O2 C19 H19A 110.3 . . ?
O2 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
C9 C20 H20A 110.8 . . ?
C9 C20 H20B 110.8 . . ?
H20A C20 H20B 108.9 . . ?
C21 C20 C9 104.7(4) . . ?
C21 C20 H20A 110.8 . . ?
C21 C20 H20B 110.8 . . ?
C20 C21 C31 113.5(4) . . ?
C22 C21 C20 104.6(5) . . ?
C22 C21 C30 103.4(4) . . ?
C22 C21 C31 114.0(5) . . ?
C30 C21 C20 112.1(5) . . ?
C30 C21 C31 108.8(5) . . ?
O6 C22 C21 103.8(4) . . ?
O6 C22 C23 104.5(4) . . ?
O7 C22 O6 111.5(4) . . ?
O7 C22 C21 111.8(4) . . ?
O7 C22 C23 117.3(4) . . ?
C21 C22 C23 106.8(5) . . ?
O11 C23 C22 109.3(4) . . ?
O11 C23 C24 103.4(5) . . ?
O11 C23 C29 109.0(5) . . ?
C24 C23 C22 113.2(5) . . ?
C29 C23 C22 103.7(5) . . ?
C29 C23 C24 118.0(5) . . ?
C23 C24 H24 125.7 . . ?
C25 C24 C23 108.7(6) . . ?
C25 C24 H24 125.7 . . ?
C24 C25 H25 123.4 . . ?
C24 C25 C26 113.2(6) . . ?
C26 C25 H25 123.4 . . ?
O11 C26 C25 102.4(5) . . ?
O11 C26 C27 109.1(6) . . ?
O11 C26 C28 107.9(6) . . ?
C25 C26 C27 112.3(6) . . ?
C25 C26 C28 114.2(7) . . ?
C28 C26 C27 110.6(7) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 H29A 110.6 . . ?
C23 C29 H29B 110.6 . . ?
C23 C29 C30 105.5(4) . . ?
H29A C29 H29B 108.8 . . ?
C30 C29 H29A 110.6 . . ?
C30 C29 H29B 110.6 . . ?
O10 C30 C21 125.9(5) . . ?
O10 C30 C29 124.6(6) . . ?
C29 C30 C21 109.5(5) . . ?
C21 C31 H31A 108.3 . . ?
C21 C31 H31B 108.3 . . ?
H31A C31 H31B 107.4 . . ?
C32 C31 C21 116.1(6) . . ?
C32 C31 H31A 108.3 . . ?
C32 C31 H31B 108.3 . . ?
C31 C32 H32 116.7 . . ?
C33 C32 C31 126.7(7) . . ?
C33 C32 H32 116.7 . . ?
C32 C33 C34 123.4(8) . . ?
C32 C33 C35 121.1(8) . . ?
C34 C33 C35 115.4(6) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C36 O12 H12 147.5 . . ?
O12 C36 H36A 109.5 . . ?
O12 C36 H36B 109.5 . . ?
O12 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C16 C17 O2 1.1(8) . . . . ?
O1 C16 C17 C18 -179.4(6) . . . . ?
O2 C17 C18 C13 178.4(6) . . . . ?
O3 C12 C13 C14 173.2(6) . . . . ?
O3 C12 C13 C18 -7.4(8) . . . . ?
O4 C8 C9 O6 -75.5(5) . . . . ?
O4 C8 C9 C10 36.8(5) . . . . ?
O4 C8 C9 C20 165.8(4) . . . . ?
O5 C8 C9 O6 164.5(4) . . . . ?
O5 C8 C9 C10 -83.2(5) . . . . ?
O5 C8 C9 C20 45.8(6) . . . . ?
O6 C9 C10 C11 85.5(5) . . . . ?
O6 C9 C10 C12 -153.1(4) . . . . ?
O6 C9 C20 C21 2.1(5) . . . . ?
O6 C22 C23 O11 168.3(4) . . . . ?
O6 C22 C23 C24 53.6(6) . . . . ?
O6 C22 C23 C29 -75.5(5) . . . . ?
O7 C22 C23 O11 44.2(7) . . . . ?
O7 C22 C23 C24 -70.5(6) . . . . ?
O7 C22 C23 C29 160.4(5) . . . . ?
O8 C2 C3 O9 1.8(8) . . . . ?
O8 C2 C3 C4 -179.6(6) . . . . ?
O8 C2 C7 C6 178.4(6) . . . . ?
O9 C3 C4 C5 179.7(6) . . . . ?
O11 C23 C24 C25 0.6(6) . . . . ?
O11 C23 C29 C30 87.6(5) . . . . ?
C1 O8 C2 C3 7.0(8) . . . . ?
C1 O8 C2 C7 -172.1(7) . . . . ?
C1 O9 C3 C2 -9.8(8) . . . . ?
C1 O9 C3 C4 171.7(7) . . . . ?
C2 O8 C1 O9 -13.4(8) . . . . ?
C2 C3 C4 C5 1.4(10) . . . . ?
C3 O9 C1 O8 14.2(8) . . . . ?
C3 C2 C7 C6 -0.6(10) . . . . ?
C3 C4 C5 C6 -1.3(9) . . . . ?
C4 C5 C6 C7 0.3(9) . . . . ?
C4 C5 C6 C8 -179.7(6) . . . . ?
C5 C6 C7 C2 0.7(9) . . . . ?
C5 C6 C8 O4 -156.7(5) . . . . ?
C5 C6 C8 O5 -35.3(7) . . . . ?
C5 C6 C8 C9 87.2(6) . . . . ?
C6 C8 C9 O6 43.6(6) . . . . ?
C6 C8 C9 C10 155.9(4) . . . . ?
C6 C8 C9 C20 -75.1(6) . . . . ?
C7 C2 C3 O9 -179.1(6) . . . . ?
C7 C2 C3 C4 -0.5(10) . . . . ?
C7 C6 C8 O4 23.4(7) . . . . ?
C7 C6 C8 O5 144.7(5) . . . . ?
C7 C6 C8 C9 -92.7(6) . . . . ?
C8 O4 C11 C10 16.5(6) . . . . ?
C8 C6 C7 C2 -179.4(5) . . . . ?
C8 C9 C10 C11 -26.3(5) . . . . ?
C8 C9 C10 C12 95.1(5) . . . . ?
C8 C9 C20 C21 121.2(5) . . . . ?
C9 O6 C22 O7 -85.2(5) . . . . ?
C9 O6 C22 C21 35.3(5) . . . . ?
C9 O6 C22 C23 147.1(4) . . . . ?
C9 C10 C11 O4 7.9(6) . . . . ?
C9 C10 C12 O3 -62.6(7) . . . . ?
C9 C10 C12 C13 118.5(5) . . . . ?
C9 C20 C21 C22 18.5(5) . . . . ?
C9 C20 C21 C30 -92.9(5) . . . . ?
C9 C20 C21 C31 143.4(5) . . . . ?
C10 C9 C20 C21 -117.2(5) . . . . ?
C10 C12 C13 C14 -7.9(9) . . . . ?
C10 C12 C13 C18 171.6(5) . . . . ?
C11 O4 C8 O5 84.8(5) . . . . ?
C11 O4 C8 C6 -156.9(5) . . . . ?
C11 O4 C8 C9 -33.9(6) . . . . ?
C11 C10 C12 O3 53.1(7) . . . . ?
C11 C10 C12 C13 -125.8(5) . . . . ?
C12 C10 C11 O4 -114.3(5) . . . . ?
C12 C13 C14 C15 177.1(8) . . . . ?
C12 C13 C18 C17 -177.0(5) . . . . ?
C13 C14 C15 C16 0.6(14) . . . . ?
C14 C13 C18 C17 2.5(9) . . . . ?
C14 C15 C16 O1 179.3(8) . . . . ?
C14 C15 C16 C17 1.0(14) . . . . ?
C15 C16 C17 O2 179.7(8) . . . . ?
C15 C16 C17 C18 -0.8(12) . . . . ?
C16 O1 C19 O2 5.5(8) . . . . ?
C16 C17 C18 C13 -1.0(9) . . . . ?
C17 O2 C19 O1 -4.9(8) . . . . ?
C18 C13 C14 C15 -2.4(12) . . . . ?
C19 O1 C16 C15 177.4(9) . . . . ?
C19 O1 C16 C17 -4.2(8) . . . . ?
C19 O2 C17 C16 2.5(8) . . . . ?
C19 O2 C17 C18 -177.0(6) . . . . ?
C20 C9 C10 C11 -155.9(5) . . . . ?
C20 C9 C10 C12 -34.6(6) . . . . ?
C20 C21 C22 O6 -32.3(5) . . . . ?
C20 C21 C22 O7 88.0(5) . . . . ?
C20 C21 C22 C23 -142.4(4) . . . . ?
C20 C21 C30 O10 -61.0(8) . . . . ?
C20 C21 C30 C29 118.9(5) . . . . ?
C20 C21 C31 C32 51.6(7) . . . . ?
C21 C22 C23 O11 -82.1(6) . . . . ?
C21 C22 C23 C24 163.2(5) . . . . ?
C21 C22 C23 C29 34.1(6) . . . . ?
C21 C31 C32 C33 -116.2(7) . . . . ?
C22 O6 C9 C8 -149.4(4) . . . . ?
C22 O6 C9 C10 102.1(4) . . . . ?
C22 O6 C9 C20 -23.3(5) . . . . ?
C22 C21 C30 O10 -173.2(6) . . . . ?
C22 C21 C30 C29 6.8(6) . . . . ?
C22 C21 C31 C32 171.2(5) . . . . ?
C22 C23 C24 C25 118.7(6) . . . . ?
C22 C23 C29 C30 -28.8(6) . . . . ?
C23 O11 C26 C25 4.1(7) . . . . ?
C23 O11 C26 C27 -115.0(7) . . . . ?
C23 O11 C26 C28 124.8(7) . . . . ?
C23 C24 C25 C26 2.1(8) . . . . ?
C23 C29 C30 O10 -165.9(6) . . . . ?
C23 C29 C30 C21 14.1(6) . . . . ?
C24 C23 C29 C30 -154.9(5) . . . . ?
C24 C25 C26 O11 -3.8(8) . . . . ?
C24 C25 C26 C27 113.0(8) . . . . ?
C24 C25 C26 C28 -120.1(8) . . . . ?
C26 O11 C23 C22 -123.9(5) . . . . ?
C26 O11 C23 C24 -3.0(6) . . . . ?
C26 O11 C23 C29 123.3(5) . . . . ?
C29 C23 C24 C25 -119.9(6) . . . . ?
C30 C21 C22 O6 85.2(5) . . . . ?
C30 C21 C22 O7 -154.5(4) . . . . ?
C30 C21 C22 C23 -24.9(6) . . . . ?
C30 C21 C31 C32 -74.0(6) . . . . ?
C31 C21 C22 O6 -156.9(4) . . . . ?
C31 C21 C22 O7 -36.6(6) . . . . ?
C31 C21 C22 C23 93.0(5) . . . . ?
C31 C21 C30 O10 65.4(8) . . . . ?
C31 C21 C30 C29 -114.7(5) . . . . ?
C31 C32 C33 C34 3.8(12) . . . . ?
C31 C32 C33 C35 -175.0(6) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.107 -0.005 0.446 58.4 12.5 ?
2 0.107 0.495 0.054 58.4 12.6 ?
3 0.393 0.505 0.554 58.4 12.6 ?
4 0.607 0.005 0.946 58.4 12.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
