# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_wsj018
_database_code_depnum_ccdc_archive 'CCDC 2235350'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-11-22 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         'C26 H24 O3'
_chemical_formula_sum            'C26 H24 O3'
_chemical_formula_weight         384.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.9089(2)
_cell_length_b                   15.0721(3)
_cell_length_c                   17.4446(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2079.46(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9203
_cell_measurement_theta_min      3.88
_cell_measurement_theta_max      78.71

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.136
_exptl_absorpt_coefficient_mu    0.628
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8201
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12278
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.876
_diffrn_reflns_theta_max         79.379
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4362
_reflns_number_gt                4170
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.951
_reflns_Friedel_fraction_full    0.994

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (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)+(0.0295P)²+0.2888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 1689 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4362
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.92942(18) 0.92317(8) 0.69031(9) 0.0371(3) Uani 1 1 d . . . . .
O2 O 0.55644(17) 0.93114(8) 0.68499(7) 0.0295(3) Uani 1 1 d . . . . .
O3 O 0.50794(17) 0.81735(9) 0.60447(7) 0.0310(3) Uani 1 1 d . . . . .
C1 C 0.7147(2) 0.71608(11) 0.69774(10) 0.0229(3) Uani 1 1 d . . . . .
H1 H 0.607552 0.692482 0.683898 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7370(2) 0.80321(10) 0.68783(9) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.9010(2) 0.84532(11) 0.70541(9) 0.0228(3) Uani 1 1 d . . . . .
C4 C 1.0329(2) 0.78760(10) 0.73981(9) 0.0206(3) Uani 1 1 d . . . . .
C5 C 1.1860(2) 0.82660(11) 0.76229(10) 0.0245(3) Uani 1 1 d . . . . .
H5 H 1.202311 0.888568 0.755622 0.029 Uiso 1 1 calc R U . . .
C6 C 1.3133(2) 0.77588(12) 0.79399(11) 0.0282(4) Uani 1 1 d . . . . .
H6 H 1.416362 0.802800 0.809502 0.034 Uiso 1 1 calc R U . . .
C7 C 1.2895(2) 0.68493(13) 0.80309(11) 0.0311(4) Uani 1 1 d . . . . .
H7 H 1.377241 0.649616 0.824365 0.037 Uiso 1 1 calc R U . . .
C8 C 1.1386(2) 0.64570(12) 0.78128(11) 0.0293(4) Uani 1 1 d . . . . .
H8 H 1.123997 0.583556 0.787548 0.035 Uiso 1 1 calc R U . . .
C9 C 1.0075(2) 0.69655(11) 0.75013(9) 0.0220(3) Uani 1 1 d . . . . .
C10 C 0.8423(2) 0.65223(10) 0.72855(10) 0.0225(3) Uani 1 1 d . . . . .
C11 C 0.8789(2) 0.58173(12) 0.66452(11) 0.0294(4) Uani 1 1 d . . . . .
H11A H 0.943567 0.610270 0.622663 0.035 Uiso 1 1 calc R U . . .
H11B H 0.949881 0.533834 0.686236 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7245(3) 0.54286(11) 0.63278(11) 0.0307(4) Uani 1 1 d . . . . .
C13 C 0.5912(3) 0.51815(12) 0.60826(11) 0.0313(4) Uani 1 1 d . . . . .
C14 C 0.4301(2) 0.49071(11) 0.57805(10) 0.0272(3) Uani 1 1 d . . . . .
C15 C 0.3895(3) 0.50796(12) 0.50153(11) 0.0325(4) Uani 1 1 d . . . . .
H15 H 0.467865 0.538287 0.469651 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2354(3) 0.48096(12) 0.47209(11) 0.0361(4) Uani 1 1 d . . . . .
H16 H 0.208976 0.492348 0.419886 0.043 Uiso 1 1 calc R U . . .
C17 C 0.1198(3) 0.43758(14) 0.51807(12) 0.0375(4) Uani 1 1 d . . . . .
H17 H 0.013931 0.419401 0.497651 0.045 Uiso 1 1 calc R U . . .
C18 C 0.1589(3) 0.42063(14) 0.59433(12) 0.0361(4) Uani 1 1 d . . . . .
H18 H 0.079540 0.390718 0.626019 0.043 Uiso 1 1 calc R U . . .
C19 C 0.3125(2) 0.44704(13) 0.62433(11) 0.0318(4) Uani 1 1 d . . . . .
H19 H 0.338252 0.435456 0.676578 0.038 Uiso 1 1 calc R U . . .
C21 C 0.5927(2) 0.85937(11) 0.65982(9) 0.0229(3) Uani 1 1 d . . . . .
C22 C 0.3572(3) 0.86056(13) 0.57431(12) 0.0348(4) Uani 1 1 d . . . . .
H22A H 0.388787 0.907059 0.536870 0.042 Uiso 1 1 calc R U . . .
H22B H 0.292115 0.888505 0.616350 0.042 Uiso 1 1 calc R U . . .
C23 C 0.2542(3) 0.79011(17) 0.53628(16) 0.0528(6) Uani 1 1 d . . . . .
H23A H 0.154483 0.817037 0.512384 0.079 Uiso 1 1 calc R U . . .
H23B H 0.218075 0.746476 0.574576 0.079 Uiso 1 1 calc R U . . .
H23C H 0.322453 0.760596 0.496938 0.079 Uiso 1 1 calc R U . . .
C24 C 0.7636(2) 0.60398(11) 0.79887(10) 0.0263(3) Uani 1 1 d . . . . .
H24A H 0.654628 0.577146 0.783254 0.032 Uiso 1 1 calc R U . . .
H24B H 0.839850 0.555211 0.814662 0.032 Uiso 1 1 calc R U . . .
C25 C 0.7335(2) 0.66345(12) 0.86632(10) 0.0288(4) Uani 1 1 d . . . . .
H25 H 0.662950 0.713763 0.859045 0.035 Uiso 1 1 calc R U . . .
C26 C 0.7980(3) 0.65078(16) 0.93479(13) 0.0433(5) Uani 1 1 d . . . . .
H26 H 0.869561 0.600646 0.940778 0.052 Uiso 1 1 calc R U . . .
C27 C 0.7707(4) 0.70676(19) 1.00411(13) 0.0550(6) Uani 1 1 d . . . . .
H27A H 0.722294 0.670407 1.045185 0.082 Uiso 1 1 calc R U . . .
H27B H 0.692884 0.755253 0.991667 0.082 Uiso 1 1 calc R U . . .
H27C H 0.879103 0.731432 1.021069 0.082 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.223(2) . ?
O2 C21 1.202(2) . ?
O3 C21 1.335(2) . ?
O3 C22 1.457(2) . ?
C1 C2 1.336(2) . ?
C1 C10 1.495(2) . ?
C2 C3 1.477(2) . ?
C2 C21 1.502(2) . ?
C3 C4 1.485(2) . ?
C4 C9 1.398(2) . ?
C4 C5 1.402(2) . ?
C5 C6 1.379(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.385(3) . ?
C8 C9 1.400(2) . ?
C9 C10 1.514(2) . ?
C10 C24 1.556(2) . ?
C10 C11 1.568(2) . ?
C11 C12 1.463(3) . ?
C12 C13 1.198(3) . ?
C13 C14 1.440(3) . ?
C14 C19 1.396(3) . ?
C14 C15 1.397(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.382(3) . ?
C22 C23 1.494(3) . ?
C24 C25 1.498(3) . ?
C25 C26 1.313(3) . ?
C26 C27 1.490(3) . ?

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
C21 O3 C22 117.39(13) . . ?
C2 C1 C10 126.16(15) . . ?
C1 C2 C3 120.76(14) . . ?
C1 C2 C21 119.71(15) . . ?
C3 C2 C21 119.51(14) . . ?
O1 C3 C2 121.92(15) . . ?
O1 C3 C4 121.36(16) . . ?
C2 C3 C4 116.69(14) . . ?
C9 C4 C5 119.96(15) . . ?
C9 C4 C3 121.75(14) . . ?
C5 C4 C3 118.29(14) . . ?
C6 C5 C4 120.66(15) . . ?
C5 C6 C7 119.51(16) . . ?
C8 C7 C6 120.35(16) . . ?
C7 C8 C9 120.76(16) . . ?
C4 C9 C8 118.74(15) . . ?
C4 C9 C10 121.65(14) . . ?
C8 C9 C10 119.61(14) . . ?
C1 C10 C9 112.83(13) . . ?
C1 C10 C24 108.29(13) . . ?
C9 C10 C24 110.82(14) . . ?
C1 C10 C11 107.73(14) . . ?
C9 C10 C11 108.48(13) . . ?
C24 C10 C11 108.57(13) . . ?
C12 C11 C10 112.78(15) . . ?
C13 C12 C11 174.10(19) . . ?
C12 C13 C14 178.5(2) . . ?
C19 C14 C15 119.16(17) . . ?
C19 C14 C13 120.87(17) . . ?
C15 C14 C13 119.97(18) . . ?
C16 C15 C14 120.14(18) . . ?
C17 C16 C15 120.46(18) . . ?
C16 C17 C18 119.71(19) . . ?
C19 C18 C17 120.37(19) . . ?
C18 C19 C14 120.16(17) . . ?
O2 C21 O3 124.81(16) . . ?
O2 C21 C2 124.72(15) . . ?
O3 C21 C2 110.44(13) . . ?
O3 C22 C23 106.79(16) . . ?
C25 C24 C10 113.77(14) . . ?
C26 C25 C24 124.47(19) . . ?
C25 C26 C27 126.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 2.0(3) . . . . ?
C10 C1 C2 C21 -176.94(15) . . . . ?
C1 C2 C3 O1 173.22(17) . . . . ?
C21 C2 C3 O1 -7.9(2) . . . . ?
C1 C2 C3 C4 -4.6(2) . . . . ?
C21 C2 C3 C4 174.34(13) . . . . ?
O1 C3 C4 C9 -173.43(17) . . . . ?
C2 C3 C4 C9 4.4(2) . . . . ?
O1 C3 C4 C5 6.7(2) . . . . ?
C2 C3 C4 C5 -175.56(14) . . . . ?
C9 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C5 C6 -179.48(15) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C5 C4 C9 C8 -1.5(2) . . . . ?
C3 C4 C9 C8 178.54(15) . . . . ?
C5 C4 C9 C10 178.40(15) . . . . ?
C3 C4 C9 C10 -1.5(2) . . . . ?
C7 C8 C9 C4 1.4(3) . . . . ?
C7 C8 C9 C10 -178.55(17) . . . . ?
C2 C1 C10 C9 1.0(2) . . . . ?
C2 C1 C10 C24 124.02(18) . . . . ?
C2 C1 C10 C11 -118.73(18) . . . . ?
C4 C9 C10 C1 -1.2(2) . . . . ?
C8 C9 C10 C1 178.76(16) . . . . ?
C4 C9 C10 C24 -122.80(16) . . . . ?
C8 C9 C10 C24 57.1(2) . . . . ?
C4 C9 C10 C11 118.10(17) . . . . ?
C8 C9 C10 C11 -62.0(2) . . . . ?
C1 C10 C11 C12 -50.40(19) . . . . ?
C9 C10 C11 C12 -172.83(15) . . . . ?
C24 C10 C11 C12 66.67(19) . . . . ?
C19 C14 C15 C16 -0.8(3) . . . . ?
C13 C14 C15 C16 179.39(17) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 C14 -0.3(3) . . . . ?
C15 C14 C19 C18 0.6(3) . . . . ?
C13 C14 C19 C18 -179.58(18) . . . . ?
C22 O3 C21 O2 -2.1(3) . . . . ?
C22 O3 C21 C2 176.21(15) . . . . ?
C1 C2 C21 O2 137.12(18) . . . . ?
C3 C2 C21 O2 -41.8(2) . . . . ?
C1 C2 C21 O3 -41.2(2) . . . . ?
C3 C2 C21 O3 139.86(15) . . . . ?
C21 O3 C22 C23 -160.10(18) . . . . ?
C1 C10 C24 C25 -67.22(18) . . . . ?
C9 C10 C24 C25 57.03(18) . . . . ?
C11 C10 C24 C25 176.08(14) . . . . ?
C10 C24 C25 C26 -122.2(2) . . . . ?
C24 C25 C26 C27 -179.1(2) . . . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.038



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, PE'
####################################################################### 
# 
# 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_wsj025
_database_code_depnum_ccdc_archive 'CCDC 2289879'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2023-11-22 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         'C31 H26 O3'
_chemical_formula_sum            'C31 H26 O3'
_chemical_formula_weight         446.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.83070(10)
_cell_length_b                   15.5594(3)
_cell_length_c                   21.1844(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2581.13(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      68.27

_exptl_crystal_description       flake
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.576
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16167
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.524
_diffrn_reflns_theta_max         68.265
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4717
_reflns_number_gt                4449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.994

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (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)+(0.1072P)²+0.6656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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 1792 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.04(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4717
_refine_ls_number_parameters     313
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.1697
_refine_ls_wR_factor_gt          0.1655
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5376(4) 0.44524(17) 0.2593(2) 0.0649(11) Uani 1 1 d . . . . .
O2 O 0.8959(3) 0.41848(16) 0.27075(14) 0.0443(6) Uani 1 1 d . . . . .
O3 O 0.9722(3) 0.50819(17) 0.34740(14) 0.0454(6) Uani 1 1 d . . . . .
C1 C 0.7755(4) 0.63409(19) 0.29203(14) 0.0271(6) Uani 1 1 d . . . . .
H1 H 0.885211 0.649169 0.307660 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6552(4) 0.70634(17) 0.27850(13) 0.0244(6) Uani 1 1 d . . . . .
C3 C 0.4862(4) 0.67565(18) 0.25172(14) 0.0248(6) Uani 1 1 d . . . . .
C4 C 0.3621(4) 0.73537(19) 0.23414(16) 0.0321(6) Uani 1 1 d . . . . .
H4 H 0.381870 0.794842 0.241152 0.038 Uiso 1 1 calc R U . . .
C5 C 0.2100(4) 0.7090(2) 0.20650(19) 0.0383(8) Uani 1 1 d . . . . .
H5 H 0.127165 0.750473 0.194359 0.046 Uiso 1 1 calc R U . . .
C6 C 0.1788(4) 0.6227(2) 0.1966(2) 0.0454(9) Uani 1 1 d . . . . .
H6 H 0.075740 0.604742 0.176964 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2979(4) 0.5626(2) 0.2154(2) 0.0411(8) Uani 1 1 d . . . . .
H7 H 0.274787 0.503097 0.209988 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4526(4) 0.58872(19) 0.24243(16) 0.0302(6) Uani 1 1 d . . . . .
C9 C 0.5757(4) 0.5209(2) 0.26108(18) 0.0350(7) Uani 1 1 d . . . . .
C10 C 0.7441(4) 0.55071(18) 0.28434(14) 0.0271(6) Uani 1 1 d . . . . .
C11 C 0.8757(4) 0.4842(2) 0.29868(16) 0.0307(6) Uani 1 1 d . . . . .
C12 C 1.1078(6) 0.4482(3) 0.3637(3) 0.0600(12) Uani 1 1 d D . . . .
H12A H 1.206572 0.455353 0.334981 0.072 Uiso 0.28(2) 1 calc R U P A 1
H12B H 1.066618 0.388180 0.360691 0.072 Uiso 0.28(2) 1 calc R U P A 1
H12C H 1.173386 0.432429 0.325442 0.072 Uiso 0.72(2) 1 calc R U P A 2
H12D H 1.058559 0.395152 0.381977 0.072 Uiso 0.72(2) 1 calc R U P A 2
C13X C 1.158(4) 0.470(2) 0.4316(11) 0.074(3) Uani 0.28(2) 1 d D . P A 1
H13A H 1.055251 0.473230 0.457845 0.111 Uiso 0.28(2) 1 calc R U P A 1
H13B H 1.217644 0.525245 0.432471 0.111 Uiso 0.28(2) 1 calc R U P A 1
H13C H 1.233751 0.424941 0.448087 0.111 Uiso 0.28(2) 1 calc R U P A 1
C13Y C 1.2198(13) 0.4898(7) 0.4096(6) 0.074(3) Uani 0.72(2) 1 d D . P A 2
H13D H 1.281347 0.537058 0.389101 0.111 Uiso 0.72(2) 1 calc R U P A 2
H13E H 1.301963 0.447833 0.425898 0.111 Uiso 0.72(2) 1 calc R U P A 2
H13F H 1.151243 0.512514 0.444499 0.111 Uiso 0.72(2) 1 calc R U P A 2
C21 C 0.7427(4) 0.76912(18) 0.23110(15) 0.0293(6) Uani 1 1 d . . . . .
H21A H 0.671876 0.821581 0.227423 0.035 Uiso 1 1 calc R U . . .
H21B H 0.854965 0.786405 0.248467 0.035 Uiso 1 1 calc R U . . .
C22 C 0.7685(4) 0.7332(2) 0.16811(15) 0.0308(6) Uani 1 1 d . . . . .
C23 C 0.7871(4) 0.7063(2) 0.11577(17) 0.0364(7) Uani 1 1 d . . . . .
C24 C 0.8087(4) 0.6787(3) 0.05141(18) 0.0411(8) Uani 1 1 d . . . . .
C25 C 0.8776(7) 0.7347(5) 0.0070(2) 0.0759(19) Uani 1 1 d . . . . .
H25 H 0.915277 0.790137 0.019544 0.091 Uiso 1 1 calc R U . . .
C26 C 0.8915(8) 0.7093(6) -0.0561(2) 0.095(3) Uani 1 1 d . . . . .
H26 H 0.935266 0.748357 -0.086540 0.114 Uiso 1 1 calc R U . . .
C27 C 0.8433(7) 0.6297(5) -0.0741(2) 0.0773(18) Uani 1 1 d . . . . .
H27 H 0.854708 0.612976 -0.116992 0.093 Uiso 1 1 calc R U . . .
C28 C 0.7785(11) 0.5734(4) -0.0314(3) 0.091(2) Uani 1 1 d . . . . .
H28 H 0.746306 0.517319 -0.044645 0.110 Uiso 1 1 calc R U . . .
C29 C 0.7586(10) 0.5976(3) 0.0327(2) 0.0727(16) Uani 1 1 d . . . . .
H29A H 0.711369 0.558439 0.062429 0.087 Uiso 1 1 calc R U . . .
C31 C 0.6316(4) 0.7583(2) 0.34060(16) 0.0340(7) Uani 1 1 d . . . . .
H31A H 0.741975 0.785480 0.351653 0.041 Uiso 1 1 calc R U . . .
H31B H 0.548396 0.805039 0.332753 0.041 Uiso 1 1 calc R U . . .
C32 C 0.5719(4) 0.7072(2) 0.39552(17) 0.0380(7) Uani 1 1 d . . . . .
H32 H 0.466775 0.677138 0.391855 0.046 Uiso 1 1 calc R U . . .
C33 C 0.6574(5) 0.7011(3) 0.44939(19) 0.0481(9) Uani 1 1 d . . . . .
H33 H 0.766257 0.727993 0.450182 0.058 Uiso 1 1 calc R U . . .
C34 C 0.6051(5) 0.6579(3) 0.50807(19) 0.0461(9) Uani 1 1 d . . . . .
C35 C 0.4541(7) 0.6140(3) 0.5150(2) 0.0582(11) Uani 1 1 d . . . . .
H35 H 0.379261 0.609695 0.479843 0.070 Uiso 1 1 calc R U . . .
C36 C 0.4075(7) 0.5760(4) 0.5711(2) 0.0667(13) Uani 1 1 d . . . . .
H36 H 0.301806 0.546298 0.574211 0.080 Uiso 1 1 calc R U . . .
C37 C 0.5137(7) 0.5809(3) 0.6227(2) 0.0586(11) Uani 1 1 d . . . . .
H37 H 0.481127 0.556237 0.661950 0.070 Uiso 1 1 calc R U . . .
C38 C 0.6665(8) 0.6219(4) 0.6165(2) 0.0765(17) Uani 1 1 d . . . . .
H38 H 0.741594 0.625516 0.651634 0.092 Uiso 1 1 calc R U . . .
C39 C 0.7130(8) 0.6582(4) 0.5597(3) 0.0760(18) Uani 1 1 d . . . . .
H39 H 0.822323 0.684130 0.555962 0.091 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.215(4) . ?
O2 C11 1.192(4) . ?
O3 C11 1.333(4) . ?
O3 C12 1.455(4) . ?
C1 C10 1.330(4) . ?
C1 C2 1.494(4) . ?
C2 C3 1.518(4) . ?
C2 C31 1.556(4) . ?
C2 C21 1.560(4) . ?
C3 C8 1.392(4) . ?
C3 C4 1.395(4) . ?
C4 C5 1.389(5) . ?
C5 C6 1.381(5) . ?
C6 C7 1.379(5) . ?
C7 C8 1.400(5) . ?
C8 C9 1.483(4) . ?
C9 C10 1.482(4) . ?
C10 C11 1.492(4) . ?
C12 C13Y 1.461(9) . ?
C12 C13X 1.53(2) . ?
C21 C22 1.461(5) . ?
C22 C23 1.194(5) . ?
C23 C24 1.439(5) . ?
C24 C29 1.380(7) . ?
C24 C25 1.391(7) . ?
C25 C26 1.398(7) . ?
C26 C27 1.349(11) . ?
C27 C28 1.357(11) . ?
C28 C29 1.419(8) . ?
C31 C32 1.485(5) . ?
C32 C33 1.326(6) . ?
C33 C34 1.471(5) . ?
C34 C35 1.373(6) . ?
C34 C39 1.383(7) . ?
C35 C36 1.378(7) . ?
C36 C37 1.376(8) . ?
C37 C38 1.362(8) . ?
C38 C39 1.378(7) . ?

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
C11 O3 C12 114.7(3) . . ?
C10 C1 C2 126.4(3) . . ?
C1 C2 C3 112.6(2) . . ?
C1 C2 C31 107.7(2) . . ?
C3 C2 C31 112.1(2) . . ?
C1 C2 C21 108.5(2) . . ?
C3 C2 C21 109.9(2) . . ?
C31 C2 C21 105.7(2) . . ?
C8 C3 C4 118.6(3) . . ?
C8 C3 C2 121.6(3) . . ?
C4 C3 C2 119.9(3) . . ?
C5 C4 C3 120.9(3) . . ?
C6 C5 C4 120.2(3) . . ?
C7 C6 C5 119.7(3) . . ?
C6 C7 C8 120.4(3) . . ?
C3 C8 C7 120.2(3) . . ?
C3 C8 C9 122.1(3) . . ?
C7 C8 C9 117.7(3) . . ?
O1 C9 C10 122.2(3) . . ?
O1 C9 C8 121.4(3) . . ?
C10 C9 C8 116.4(3) . . ?
C1 C10 C9 120.7(3) . . ?
C1 C10 C11 121.6(3) . . ?
C9 C10 C11 117.7(3) . . ?
O2 C11 O3 123.3(3) . . ?
O2 C11 C10 125.9(3) . . ?
O3 C11 C10 110.8(3) . . ?
O3 C12 C13Y 108.1(5) . . ?
O3 C12 C13X 105.6(10) . . ?
C22 C21 C2 114.2(2) . . ?
C23 C22 C21 177.8(3) . . ?
C22 C23 C24 176.8(4) . . ?
C29 C24 C25 119.3(4) . . ?
C29 C24 C23 120.7(4) . . ?
C25 C24 C23 120.0(4) . . ?
C24 C25 C26 120.0(6) . . ?
C27 C26 C25 120.5(6) . . ?
C26 C27 C28 120.6(5) . . ?
C27 C28 C29 120.5(6) . . ?
C24 C29 C28 119.1(6) . . ?
C32 C31 C2 114.9(3) . . ?
C33 C32 C31 123.6(3) . . ?
C32 C33 C34 128.3(4) . . ?
C35 C34 C39 116.3(4) . . ?
C35 C34 C33 123.9(4) . . ?
C39 C34 C33 119.8(4) . . ?
C34 C35 C36 122.3(5) . . ?
C37 C36 C35 120.1(5) . . ?
C38 C37 C36 118.7(4) . . ?
C37 C38 C39 120.6(5) . . ?
C38 C39 C34 121.9(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -1.9(4) . . . . ?
C10 C1 C2 C31 122.2(3) . . . . ?
C10 C1 C2 C21 -123.8(3) . . . . ?
C1 C2 C3 C8 0.7(4) . . . . ?
C31 C2 C3 C8 -120.9(3) . . . . ?
C21 C2 C3 C8 121.8(3) . . . . ?
C1 C2 C3 C4 -177.4(3) . . . . ?
C31 C2 C3 C4 60.9(4) . . . . ?
C21 C2 C3 C4 -56.3(4) . . . . ?
C8 C3 C4 C5 -1.6(5) . . . . ?
C2 C3 C4 C5 176.6(3) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C5 C6 C7 1.2(7) . . . . ?
C5 C6 C7 C8 -2.2(7) . . . . ?
C4 C3 C8 C7 0.6(5) . . . . ?
C2 C3 C8 C7 -177.6(3) . . . . ?
C4 C3 C8 C9 -178.6(3) . . . . ?
C2 C3 C8 C9 3.2(5) . . . . ?
C6 C7 C8 C3 1.3(6) . . . . ?
C6 C7 C8 C9 -179.5(4) . . . . ?
C3 C8 C9 O1 171.6(4) . . . . ?
C7 C8 C9 O1 -7.6(6) . . . . ?
C3 C8 C9 C10 -5.9(5) . . . . ?
C7 C8 C9 C10 174.9(3) . . . . ?
C2 C1 C10 C9 -0.9(5) . . . . ?
C2 C1 C10 C11 179.1(3) . . . . ?
O1 C9 C10 C1 -172.8(4) . . . . ?
C8 C9 C10 C1 4.7(5) . . . . ?
O1 C9 C10 C11 7.2(6) . . . . ?
C8 C9 C10 C11 -175.3(3) . . . . ?
C12 O3 C11 O2 1.0(6) . . . . ?
C12 O3 C11 C10 -178.3(3) . . . . ?
C1 C10 C11 O2 -145.1(4) . . . . ?
C9 C10 C11 O2 34.9(5) . . . . ?
C1 C10 C11 O3 34.2(4) . . . . ?
C9 C10 C11 O3 -145.8(3) . . . . ?
C11 O3 C12 C13Y 169.9(7) . . . . ?
C11 O3 C12 C13X -160.3(14) . . . . ?
C1 C2 C21 C22 67.6(3) . . . . ?
C3 C2 C21 C22 -56.0(3) . . . . ?
C31 C2 C21 C22 -177.1(2) . . . . ?
C29 C24 C25 C26 1.6(9) . . . . ?
C23 C24 C25 C26 -177.1(6) . . . . ?
C24 C25 C26 C27 -2.0(11) . . . . ?
C25 C26 C27 C28 0.8(11) . . . . ?
C26 C27 C28 C29 0.7(10) . . . . ?
C25 C24 C29 C28 -0.1(8) . . . . ?
C23 C24 C29 C28 178.7(5) . . . . ?
C27 C28 C29 C24 -1.1(10) . . . . ?
C1 C2 C31 C32 -56.0(4) . . . . ?
C3 C2 C31 C32 68.5(3) . . . . ?
C21 C2 C31 C32 -171.9(3) . . . . ?
C2 C31 C32 C33 121.7(4) . . . . ?
C31 C32 C33 C34 175.0(4) . . . . ?
C32 C33 C34 C35 1.6(8) . . . . ?
C32 C33 C34 C39 179.8(5) . . . . ?
C39 C34 C35 C36 3.3(8) . . . . ?
C33 C34 C35 C36 -178.5(5) . . . . ?
C34 C35 C36 C37 -0.2(9) . . . . ?
C35 C36 C37 C38 -1.7(9) . . . . ?
C36 C37 C38 C39 0.4(10) . . . . ?
C37 C38 C39 C34 2.9(12) . . . . ?
C35 C34 C39 C38 -4.6(10) . . . . ?
C33 C34 C39 C38 177.1(6) . . . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.070



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, PE'
