# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_cu_20220830ZDY_0m
_database_code_depnum_ccdc_archive 'CCDC 2204357'
loop_
_audit_author_name
_audit_author_address
'Yunpeng Sun'
;Anhui University of Chinese Medicine
China
;
_audit_update_record             
;
2022-08-30 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H29 O6'
_chemical_formula_weight         425.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.070(3)
_cell_length_b                   10.261(2)
_cell_length_c                   21.377(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2209.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4016
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      60.75

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.741
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33459
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.136
_diffrn_reflns_theta_max         66.906
_diffrn_reflns_theta_full        66.906
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3905
_reflns_number_gt                2406
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.993
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0800P)²+3.0000P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3905
_refine_ls_number_parameters     305
_refine_ls_number_restraints     258
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0997
_refine_ls_wR_factor_ref         0.2583
_refine_ls_wR_factor_gt          0.2359
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      1.092
_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
C4 C 0.8610(11) 0.3147(18) 0.2978(5) 0.140(3) Uani 1 1 d . U . . .
C4' C 0.2914(11) 0.6901(10) 0.3876(5) 0.107(3) Uani 1 1 d . U . . .
H4' H 0.316702 0.670883 0.431903 0.129 Uiso 1 1 calc R U . . .
C5 C 0.7522(10) 0.4026(13) 0.3291(4) 0.115(3) Uani 1 1 d . U . . .
H5 H 0.665867 0.371473 0.311552 0.138 Uiso 1 1 calc R U . . .
C5' C 0.3462(10) 0.5909(9) 0.3433(4) 0.095(2) Uani 1 1 d . U . . .
H5' H 0.269796 0.555492 0.318680 0.114 Uiso 1 1 calc R U . . .
C6 C 0.7446(11) 0.5455(13) 0.3272(5) 0.123(3) Uani 1 1 d . U . . .
H6 H 0.794896 0.598167 0.299359 0.148 Uiso 1 1 calc R U . . .
C6' C 0.4275(9) 0.4724(8) 0.3677(4) 0.084(2) Uani 1 1 d . U . . .
H6' H 0.464083 0.432844 0.328582 0.100 Uiso 1 1 calc R U . . .
C7 C 0.6518(11) 0.5967(10) 0.3724(4) 0.108(3) Uani 1 1 d . U . . .
C7' C 0.3442(11) 0.3648(9) 0.3949(5) 0.103(2) Uani 1 1 d . U . . .
C8 C 0.5531(8) 0.5045(7) 0.4062(3) 0.0779(18) Uani 1 1 d . U . . .
C8' C 0.2706(12) 0.2845(11) 0.3436(6) 0.134(4) Uani 1 1 d . U . . .
H8'A H 0.198157 0.336818 0.326119 0.200 Uiso 1 1 calc R U . . .
H8'B H 0.234186 0.204878 0.362245 0.200 Uiso 1 1 calc R U . . .
H8'C H 0.333138 0.261377 0.310324 0.200 Uiso 1 1 calc R U . . .
C9 C 0.6229(8) 0.3774(8) 0.4287(4) 0.087(2) Uani 1 1 d . U . . .
H9A H 0.634005 0.377430 0.475194 0.104 Uiso 0.675(12) 1 calc R U P A 1
H9B H 0.659853 0.412312 0.468759 0.104 Uiso 0.325(12) 1 calc R U P A 2
C9' C 0.308(2) 0.9407(13) 0.3957(8) 0.219(7) Uani 1 1 d . U . . .
H9'A H 0.374421 1.003002 0.380613 0.329 Uiso 1 1 calc R U . . .
H9'B H 0.313515 0.934192 0.441358 0.329 Uiso 1 1 calc R U . . .
H9'C H 0.219098 0.970694 0.383749 0.329 Uiso 1 1 calc R U . . .
C10 C 0.7567(9) 0.3501(9) 0.3957(4) 0.093(2) Uani 1 1 d . U . . .
C10' C 0.2422(13) 0.4096(12) 0.4434(5) 0.131(4) Uani 1 1 d . U . . .
H10A H 0.173465 0.461833 0.422816 0.197 Uiso 1 1 calc R U . . .
H10B H 0.286531 0.462364 0.475420 0.197 Uiso 1 1 calc R U . . .
H10C H 0.201257 0.333279 0.463127 0.197 Uiso 1 1 calc R U . . .
C11 C 0.6554(14) 0.7097(11) 0.4073(6) 0.132(3) Uani 1 1 d . U . . .
C12 C 0.5694(13) 0.6984(10) 0.4606(6) 0.120(3) Uani 1 1 d . U . . .
C13 C 0.7470(16) 0.8210(13) 0.3936(8) 0.178(6) Uani 1 1 d . U . . .
H13A H 0.696197 0.902343 0.392402 0.267 Uiso 1 1 calc R U . . .
H13B H 0.790139 0.806895 0.353075 0.267 Uiso 1 1 calc R U . . .
H13C H 0.814780 0.826492 0.426430 0.267 Uiso 1 1 calc R U . . .
C14 C 0.8654(10) 0.4150(11) 0.4345(5) 0.110(3) Uani 1 1 d . U . . .
H14A H 0.885879 0.360575 0.470856 0.165 Uiso 1 1 calc R U . . .
H14B H 0.834691 0.500755 0.448607 0.165 Uiso 1 1 calc R U . . .
H14C H 0.945326 0.425503 0.408819 0.165 Uiso 1 1 calc R U . . .
C15 C 0.9413(12) 0.368(2) 0.2531(6) 0.199(7) Uani 1 1 d . U . . .
H15A H 1.010399 0.318081 0.234871 0.239 Uiso 1 1 calc R U . . .
H15B H 0.927904 0.456048 0.240208 0.239 Uiso 1 1 calc R U . . .
C1 C 0.7855(11) 0.2036(13) 0.3862(6) 0.131(3) Uani 1 1 d . U . . .
H1 H 0.717663 0.138167 0.399582 0.157 Uiso 1 1 calc R U . . .
O1 O 0.5443(11) 0.2621(9) 0.4079(6) 0.091(2) Uani 0.675(12) 1 d . U P A 1
O2 O 0.4164(9) 0.2849(9) 0.4401(5) 0.096(3) Uani 0.675(12) 1 d . U P A 1
O1A O 0.533(2) 0.2969(17) 0.4537(10) 0.090(3) Uani 0.325(12) 1 d . U P A 2
O2A O 0.469(3) 0.260(2) 0.3981(13) 0.095(4) Uani 0.325(12) 1 d . U P A 2
O3 O 0.5139(6) 0.5745(6) 0.4634(3) 0.0943(16) Uani 1 1 d . U . . .
O4 O 0.5471(10) 0.7737(8) 0.5037(5) 0.166(4) Uani 1 1 d . U . . .
O5 O 0.4866(12) 0.6319(10) 0.2511(4) 0.168(4) Uani 1 1 d . U . . .
O6 O 0.1494(9) 0.6914(14) 0.3793(4) 0.181(4) Uani 1 1 d . U . . .
H6A H 0.113195 0.722627 0.411328 0.271 Uiso 1 1 calc R U . . .
C1' C 0.4309(14) 0.6700(12) 0.2987(5) 0.126(3) Uani 1 1 d . U . . .
C2 C 0.9314(13) 0.1631(15) 0.3828(6) 0.158(4) Uani 1 1 d . U . . .
H2A H 0.999427 0.228738 0.393983 0.189 Uiso 1 1 calc R U . . .
H2B H 0.954221 0.072057 0.393607 0.189 Uiso 1 1 calc R U . . .
C2' C 0.4175(16) 0.8149(14) 0.3188(7) 0.152(4) Uani 1 1 d . U . . .
H2' H 0.460142 0.887590 0.300030 0.183 Uiso 1 1 calc R U . . .
C3 C 0.8543(14) 0.1851(17) 0.3278(7) 0.153(4) Uani 1 1 d . U . . .
H3 H 0.829770 0.108369 0.301440 0.183 Uiso 1 1 calc R U . . .
C3' C 0.3320(17) 0.8180(13) 0.3690(6) 0.149(4) Uani 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
C4 C15 1.367(18) . ?
C4 C3 1.48(2) . ?
C4 C5 1.570(16) . ?
C4' C3' 1.431(17) . ?
C4' O6 1.441(14) . ?
C4' C5' 1.496(13) . ?
C5 C6 1.468(17) . ?
C5 C10 1.523(13) . ?
C5' C1' 1.515(15) . ?
C5' C6' 1.556(11) . ?
C6 C7 1.444(15) . ?
C6' C7' 1.504(12) . ?
C6' C8 1.545(11) . ?
C7 C11 1.379(14) . ?
C7 C8 1.551(12) . ?
C7' O2 1.461(13) . ?
C7' C10' 1.531(15) . ?
C7' C8' 1.558(14) . ?
C7' O2A 1.65(3) . ?
C8 O3 1.472(9) . ?
C8 C9 1.558(11) . ?
C9 O1A 1.34(2) . ?
C9 O1 1.492(14) . ?
C9 C10 1.546(12) . ?
C9' C3' 1.404(17) . ?
C10 C14 1.526(12) . ?
C10 C1 1.544(15) . ?
C11 C12 1.437(16) . ?
C11 C13 1.497(16) . ?
C12 O4 1.223(12) . ?
C12 O3 1.389(12) . ?
C1 C3 1.440(17) . ?
C1 C2 1.528(16) . ?
O1 O2 1.479(17) . ?
O1A O2A 1.40(4) . ?
O5 C1' 1.225(14) . ?
C1' C2' 1.554(19) . ?
C2 C3 1.426(17) . ?
C2' C3' 1.376(19) . ?

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
C15 C4 C3 133.9(16) . . ?
C15 C4 C5 118.6(16) . . ?
C3 C4 C5 107.4(10) . . ?
C3' C4' O6 104.0(11) . . ?
C3' C4' C5' 110.0(10) . . ?
O6 C4' C5' 107.0(9) . . ?
C6 C5 C10 112.4(9) . . ?
C6 C5 C4 126.8(11) . . ?
C10 C5 C4 100.1(9) . . ?
C4' C5' C1' 104.0(8) . . ?
C4' C5' C6' 120.9(7) . . ?
C1' C5' C6' 109.5(8) . . ?
C7 C6 C5 112.2(9) . . ?
C7' C6' C8 114.1(7) . . ?
C7' C6' C5' 114.2(8) . . ?
C8 C6' C5' 116.3(7) . . ?
C11 C7 C6 130.6(11) . . ?
C11 C7 C8 106.1(9) . . ?
C6 C7 C8 120.3(9) . . ?
O2 C7' C6' 113.0(8) . . ?
O2 C7' C10' 93.1(9) . . ?
C6' C7' C10' 114.6(8) . . ?
O2 C7' C8' 113.9(9) . . ?
C6' C7' C8' 112.5(9) . . ?
C10' C7' C8' 108.4(9) . . ?
C6' C7' O2A 94.0(10) . . ?
C10' C7' O2A 132.5(13) . . ?
C8' C7' O2A 92.7(11) . . ?
O3 C8 C6' 109.1(6) . . ?
O3 C8 C7 105.2(6) . . ?
C6' C8 C7 114.0(6) . . ?
O3 C8 C9 105.9(6) . . ?
C6' C8 C9 110.8(6) . . ?
C7 C8 C9 111.4(7) . . ?
O1A C9 C10 131.4(11) . . ?
O1 C9 C10 100.5(8) . . ?
O1A C9 C8 109.5(10) . . ?
O1 C9 C8 109.4(7) . . ?
C10 C9 C8 113.8(7) . . ?
C5 C10 C14 112.0(8) . . ?
C5 C10 C1 103.1(9) . . ?
C14 C10 C1 111.2(9) . . ?
C5 C10 C9 109.7(8) . . ?
C14 C10 C9 107.3(7) . . ?
C1 C10 C9 113.6(8) . . ?
C7 C11 C12 110.2(9) . . ?
C7 C11 C13 123.5(13) . . ?
C12 C11 C13 126.0(12) . . ?
O4 C12 O3 118.2(12) . . ?
O4 C12 C11 131.1(12) . . ?
O3 C12 C11 110.5(9) . . ?
C3 C1 C2 57.3(8) . . ?
C3 C1 C10 109.4(13) . . ?
C2 C1 C10 116.9(11) . . ?
O2 O1 C9 101.4(9) . . ?
C7' O2 O1 102.4(9) . . ?
C9 O1A O2A 97.9(19) . . ?
O1A O2A C7' 102.1(18) . . ?
C12 O3 C8 107.6(7) . . ?
O5 C1' C5' 127.5(12) . . ?
O5 C1' C2' 125.1(12) . . ?
C5' C1' C2' 106.8(10) . . ?
C3 C2 C1 58.2(9) . . ?
C3' C2' C1' 107.0(12) . . ?
C2 C3 C1 64.5(9) . . ?
C2 C3 C4 118.4(14) . . ?
C1 C3 C4 106.3(12) . . ?
C2' C3' C9' 116.5(16) . . ?
C2' C3' C4' 112.0(13) . . ?
C9' C3' C4' 131.3(15) . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.062

