# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_20240510a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2368290'
loop_
_audit_author_name
_audit_author_address
'Xin-Xing Wu' lzu
_audit_update_record             
;
2024-07-05 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C69 H54 Cl2 N0 O4'
_chemical_formula_weight         1018.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   24.585(4)
_cell_length_b                   9.4237(15)
_cell_length_c                   23.169(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.207(3)
_cell_angle_gamma                90
_cell_volume                     5336.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4403
_cell_measurement_theta_min      2.295
_cell_measurement_theta_max      4.4369

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             2136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15578
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.859
_diffrn_reflns_theta_max         27.617
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6068
_reflns_number_gt                3549
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0522P)²+17.6229P] 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_number_reflns         6068
_refine_ls_number_parameters     340
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0905
_refine_ls_wR_factor_ref         0.2357
_refine_ls_wR_factor_gt          0.2081
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.170
_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
C1 C 0.61590(17) 0.4832(5) 0.32062(17) 0.0506(10) Uani 1 1 d . . . . .
C2 C 0.57216(16) 0.5704(4) 0.34390(17) 0.0492(10) Uani 1 1 d . . . . .
H2A H 0.540450 0.572414 0.315101 0.059 Uiso 1 1 calc R U . . .
H2B H 0.585326 0.667099 0.349167 0.059 Uiso 1 1 calc R U . . .
C3 C 0.55377(14) 0.5173(4) 0.40234(16) 0.0388(8) Uani 1 1 d . . . . .
C4 C 0.50741(17) 0.6142(5) 0.41732(19) 0.0541(11) Uani 1 1 d . . . . .
H4A H 0.477769 0.610108 0.386785 0.081 Uiso 1 1 calc R U . . .
H4B H 0.520558 0.709996 0.421529 0.081 Uiso 1 1 calc R U . . .
H4C H 0.494796 0.583435 0.453066 0.081 Uiso 1 1 calc R U . . .
C5 C 0.63334(17) 0.3302(6) 0.24359(19) 0.0616(13) Uani 1 1 d . . . . .
C6 C 0.6532(2) 0.3834(6) 0.1965(2) 0.0702(14) Uani 1 1 d . . . . .
H6 H 0.643190 0.474166 0.183693 0.084 Uiso 1 1 calc R U . . .
C7 C 0.6893(2) 0.3022(9) 0.1662(2) 0.0929(19) Uani 1 1 d . U . . .
H7 H 0.702721 0.338379 0.133199 0.112 Uiso 1 1 calc R U . . .
C8 C 0.7046(2) 0.1672(8) 0.1866(3) 0.0892(19) Uani 1 1 d . U . . .
H8 H 0.728938 0.113714 0.167559 0.107 Uiso 1 1 calc R U . . .
C9 C 0.68362(17) 0.1123(6) 0.2351(2) 0.0659(14) Uani 1 1 d . . . . .
C10 C 0.64606(16) 0.1957(6) 0.2650(2) 0.0603(13) Uani 1 1 d . . . . .
C11 C 0.62456(17) 0.1329(5) 0.3139(2) 0.0582(12) Uani 1 1 d . . . . .
H11 H 0.599997 0.183765 0.333725 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6393(2) 0.0017(6) 0.3316(2) 0.0761(15) Uani 1 1 d . . . . .
H12 H 0.624522 -0.037056 0.363349 0.091 Uiso 1 1 calc R U . . .
C13 C 0.6758(2) -0.0768(7) 0.3040(3) 0.0866(18) Uani 1 1 d . . . . .
H13 H 0.685547 -0.167363 0.317356 0.104 Uiso 1 1 calc R U . . .
C14 C 0.6973(2) -0.0231(7) 0.2578(3) 0.0765(16) Uani 1 1 d . . . . .
H14 H 0.722350 -0.077619 0.240068 0.092 Uiso 1 1 calc R U . . .
C15 C 0.53484(14) 0.3652(4) 0.39950(16) 0.0397(9) Uani 1 1 d . . . . .
C16 C 0.49388(15) 0.3034(5) 0.36223(18) 0.0506(10) Uani 1 1 d . . . . .
H16 H 0.474570 0.356334 0.332939 0.061 Uiso 1 1 calc R U . . .
C17 C 0.48223(17) 0.1618(5) 0.3694(2) 0.0594(12) Uani 1 1 d . . . . .
H17 H 0.454356 0.119043 0.345086 0.071 Uiso 1 1 calc R U . . .
C18 C 0.51147(19) 0.0831(5) 0.4121(2) 0.0618(12) Uani 1 1 d . . . . .
H18 H 0.503114 -0.012404 0.416129 0.074 Uiso 1 1 calc R U . . .
C19 C 0.55318(17) 0.1433(4) 0.44936(19) 0.0510(10) Uani 1 1 d . . . . .
H19 H 0.573069 0.089031 0.477782 0.061 Uiso 1 1 calc R U . . .
C20 C 0.56450(14) 0.2863(4) 0.44318(16) 0.0381(8) Uani 1 1 d . . . . .
C21 C 0.64383(14) 0.3360(4) 0.52537(16) 0.0372(8) Uani 1 1 d . . . . .
C22 C 0.62716(16) 0.2560(4) 0.57029(18) 0.0472(10) Uani 1 1 d . . . . .
H22 H 0.590689 0.228962 0.569173 0.057 Uiso 1 1 calc R U . . .
C23 C 0.66379(19) 0.2157(5) 0.61674(18) 0.0563(11) Uani 1 1 d . . . . .
H23 H 0.651719 0.162896 0.646775 0.068 Uiso 1 1 calc R U . . .
C24 C 0.7178(2) 0.2530(5) 0.6189(2) 0.0640(13) Uani 1 1 d . . . . .
H24 H 0.742391 0.226264 0.650322 0.077 Uiso 1 1 calc R U . . .
C25 C 0.73521(18) 0.3302(5) 0.5742(2) 0.0623(13) Uani 1 1 d . . . . .
H25 H 0.771942 0.354660 0.575115 0.075 Uiso 1 1 calc R U . . .
C26 C 0.69887(16) 0.3718(4) 0.52799(18) 0.0500(10) Uani 1 1 d . . . . .
H26 H 0.711282 0.424605 0.498130 0.060 Uiso 1 1 calc R U . . .
C27 C 0.60485(14) 0.3813(4) 0.47564(15) 0.0356(8) Uani 1 1 d . . . . .
C28 C 0.59974(14) 0.5125(4) 0.45224(15) 0.0370(8) Uani 1 1 d . . . . .
C29 C 0.62775(15) 0.6454(4) 0.47343(16) 0.0391(9) Uani 1 1 d . . . . .
C30 C 0.67039(17) 0.7029(4) 0.44764(19) 0.0520(10) Uani 1 1 d . . . . .
H30 H 0.683624 0.655389 0.416853 0.062 Uiso 1 1 calc R U . . .
C31 C 0.69402(19) 0.8300(5) 0.4666(2) 0.0608(12) Uani 1 1 d . . . . .
H31 H 0.723048 0.866793 0.448696 0.073 Uiso 1 1 calc R U . . .
C32 C 0.67494(18) 0.9019(4) 0.5115(2) 0.0557(11) Uani 1 1 d . . . . .
H32 H 0.690470 0.988259 0.523721 0.067 Uiso 1 1 calc R U . . .
C33 C 0.63319(19) 0.8467(5) 0.5380(2) 0.0587(12) Uani 1 1 d . . . . .
H33 H 0.620494 0.894774 0.568925 0.070 Uiso 1 1 calc R U . . .
C34 C 0.60928(18) 0.7190(5) 0.51943(18) 0.0535(11) Uani 1 1 d . . . . .
H34 H 0.580624 0.682313 0.537948 0.064 Uiso 1 1 calc R U . . .
C35 C 0.500000 0.9212(9) 0.250000 0.092(3) Uani 1 2 d S T P . .
H35A H 0.479787 0.981995 0.221464 0.110 Uiso 0.5 1 calc R U P . .
H35B H 0.520213 0.981995 0.278536 0.110 Uiso 0.5 1 calc R U P . .
Cl1 Cl 0.45404(6) 0.82161(17) 0.28416(6) 0.0852(5) Uani 1 1 d . . . . .
O1 O 0.59531(11) 0.4122(4) 0.27207(13) 0.0633(9) Uani 1 1 d . . . . .
O2 O 0.66223(12) 0.4753(4) 0.33995(14) 0.0730(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.180(5) . ?
C1 O1 1.359(5) . ?
C1 C2 1.500(6) . ?
C2 C3 1.556(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C15 1.507(5) . ?
C3 C28 1.528(5) . ?
C3 C4 1.530(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.340(7) . ?
C5 C10 1.384(7) . ?
C5 O1 1.429(5) . ?
C6 C7 1.415(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.394(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(8) . ?
C8 H8 0.9300 . ?
C9 C14 1.407(8) . ?
C9 C10 1.446(6) . ?
C10 C11 1.429(7) . ?
C11 C12 1.341(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.346(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.382(5) . ?
C15 C20 1.396(5) . ?
C16 C17 1.379(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(5) . ?
C19 H19 0.9300 . ?
C20 C27 1.480(5) . ?
C21 C22 1.383(5) . ?
C21 C26 1.389(5) . ?
C21 C27 1.480(5) . ?
C22 C23 1.380(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.351(5) . ?
C28 C29 1.487(5) . ?
C29 C30 1.373(5) . ?
C29 C34 1.388(6) . ?
C30 C31 1.382(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.366(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.356(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.387(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 Cl1 1.726(5) 2_655 ?
C35 Cl1 1.726(5) . ?
C35 H35A 0.9700 . ?
C35 H35B 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
O2 C1 O1 122.7(4) . . ?
O2 C1 C2 126.8(4) . . ?
O1 C1 C2 110.5(3) . . ?
C1 C2 C3 115.1(3) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C15 C3 C28 101.8(3) . . ?
C15 C3 C4 110.1(3) . . ?
C28 C3 C4 110.8(3) . . ?
C15 C3 C2 112.7(3) . . ?
C28 C3 C2 114.0(3) . . ?
C4 C3 C2 107.4(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 123.2(5) . . ?
C6 C5 O1 119.2(5) . . ?
C10 C5 O1 117.6(4) . . ?
C5 C6 C7 120.3(6) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 119.1(6) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 120.4(6) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C14 123.1(5) . . ?
C8 C9 C10 119.9(6) . . ?
C14 C9 C10 117.0(5) . . ?
C5 C10 C11 125.1(4) . . ?
C5 C10 C9 117.2(5) . . ?
C11 C10 C9 117.7(5) . . ?
C12 C11 C10 120.9(5) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 121.6(6) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 120.1(6) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 122.7(5) . . ?
C13 C14 H14 118.7 . . ?
C9 C14 H14 118.7 . . ?
C16 C15 C20 121.1(4) . . ?
C16 C15 C3 128.9(3) . . ?
C20 C15 C3 109.9(3) . . ?
C17 C16 C15 118.6(4) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 121.4(4) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 118.4(4) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C15 119.8(4) . . ?
C19 C20 C27 131.8(3) . . ?
C15 C20 C27 108.4(3) . . ?
C22 C21 C26 117.8(3) . . ?
C22 C21 C27 121.6(3) . . ?
C26 C21 C27 120.6(3) . . ?
C21 C22 C23 121.0(4) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 120.4(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.3(4) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 120.6(4) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 120.8(4) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C28 C27 C21 126.9(3) . . ?
C28 C27 C20 108.8(3) . . ?
C21 C27 C20 124.3(3) . . ?
C27 C28 C29 128.2(3) . . ?
C27 C28 C3 111.1(3) . . ?
C29 C28 C3 120.2(3) . . ?
C30 C29 C34 117.8(4) . . ?
C30 C29 C28 122.5(4) . . ?
C34 C29 C28 119.7(4) . . ?
C29 C30 C31 121.2(4) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C32 C31 C30 120.3(4) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C33 C32 C31 119.6(4) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C34 120.6(4) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C29 C34 C33 120.5(4) . . ?
C29 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
Cl1 C35 Cl1 114.1(5) 2_655 . ?
Cl1 C35 H35A 108.7 2_655 . ?
Cl1 C35 H35A 108.7 . . ?
Cl1 C35 H35B 108.7 2_655 . ?
Cl1 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
C1 O1 C5 116.4(3) . . ?

_refine_diff_density_max         0.587
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.053



