# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_xuj022
_database_code_depnum_ccdc_archive 'CCDC 2331715'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2024-02-08 deposited with the CCDC.	2024-10-14 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 H28 O'
_chemical_formula_sum            'C26 H28 O'
_chemical_formula_weight         356.48

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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   13.2149(3)
_cell_length_b                   5.50840(10)
_cell_length_c                   13.7281(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.5190(10)
_cell_angle_gamma                90
_cell_volume                     992.85(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      68.26

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    0.536
_shelx_estimated_absorpt_T_min   0.726
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7025
_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            12921
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.240
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3545
_reflns_number_gt                3421
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.949

_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)+(0.0373P)²+0.1181P] 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     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0123(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1431 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.09(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3545
_refine_ls_number_parameters     245
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
O O 0.41190(11) 0.2077(3) 0.19678(10) 0.0375(3) Uani 1 1 d . . . . .
C1 C 0.76903(14) 0.3483(3) 0.62987(12) 0.0259(4) Uani 1 1 d . . . . .
H1A H 0.724063 0.204088 0.627133 0.031 Uiso 1 1 calc R U . . .
H1B H 0.820494 0.319992 0.584025 0.031 Uiso 1 1 calc R U . . .
C2 C 0.70514(13) 0.5696(4) 0.59485(11) 0.0244(4) Uani 1 1 d . . . . .
H2A H 0.744081 0.718984 0.614017 0.029 Uiso 1 1 calc R U . . .
H2B H 0.642298 0.571719 0.627825 0.029 Uiso 1 1 calc R U . . .
C3 C 0.67591(12) 0.5701(3) 0.48293(11) 0.0213(3) Uani 1 1 d . . . . .
H3A H 0.639179 0.415015 0.464775 0.026 Uiso 1 1 calc R U . . .
C4 C 0.60281(12) 0.7814(3) 0.45268(11) 0.0244(4) Uani 1 1 d . . . . .
H4A H 0.540866 0.761779 0.486277 0.029 Uiso 1 1 calc R U . . .
H4B H 0.635959 0.935165 0.476029 0.029 Uiso 1 1 calc R U . . .
C5 C 0.57063(13) 0.8025(3) 0.34203(12) 0.0258(4) Uani 1 1 d . . . . .
H5A H 0.527254 0.948174 0.329441 0.031 Uiso 1 1 calc R U . . .
H5B H 0.632209 0.825505 0.308191 0.031 Uiso 1 1 calc R U . . .
C6 C 0.51269(13) 0.5819(4) 0.29888(12) 0.0271(4) Uani 1 1 d . . . . .
H6A H 0.453049 0.553597 0.334991 0.032 Uiso 1 1 calc R U . . .
H6B H 0.557354 0.437507 0.308262 0.032 Uiso 1 1 calc R U . . .
C7 C 0.47611(13) 0.6094(4) 0.18985(12) 0.0255(4) Uani 1 1 d . . . . .
H7A H 0.431940 0.754580 0.180235 0.031 Uiso 1 1 calc R U . . .
H7B H 0.535741 0.635559 0.153488 0.031 Uiso 1 1 calc R U . . .
C8 C 0.41782(12) 0.3906(3) 0.14825(12) 0.0239(4) Uani 1 1 d . . . . .
C11 C 0.82311(12) 0.3711(3) 0.73263(11) 0.0215(3) Uani 1 1 d . . . . .
C12 C 0.89102(13) 0.5605(3) 0.75622(12) 0.0257(4) Uani 1 1 d . . . . .
H12A H 0.900007 0.681417 0.708598 0.031 Uiso 1 1 calc R U . . .
C13 C 0.94582(14) 0.5753(4) 0.84837(13) 0.0306(4) Uani 1 1 d . . . . .
H13A H 0.992308 0.705220 0.863164 0.037 Uiso 1 1 calc R U . . .
C14 C 0.93316(14) 0.4021(4) 0.91878(12) 0.0327(4) Uani 1 1 d . . . . .
H14A H 0.970986 0.412273 0.981763 0.039 Uiso 1 1 calc R U . . .
C15 C 0.86502(14) 0.2136(4) 0.89699(13) 0.0313(4) Uani 1 1 d . . . . .
H15A H 0.855303 0.095103 0.945358 0.038 Uiso 1 1 calc R U . . .
C16 C 0.81072(13) 0.1978(3) 0.80410(12) 0.0256(4) Uani 1 1 d . . . . .
H16A H 0.764650 0.067012 0.789353 0.031 Uiso 1 1 calc R U . . .
C21 C 0.77015(12) 0.5787(3) 0.42904(10) 0.0212(3) Uani 1 1 d . . . . .
C22 C 0.84032(14) 0.7677(4) 0.44472(13) 0.0290(4) Uani 1 1 d . . . . .
H22A H 0.829023 0.893180 0.489715 0.035 Uiso 1 1 calc R U . . .
C23 C 0.92666(14) 0.7752(4) 0.39541(15) 0.0349(4) Uani 1 1 d . . . . .
H23A H 0.973882 0.904806 0.407119 0.042 Uiso 1 1 calc R U . . .
C24 C 0.94390(14) 0.5938(4) 0.32928(15) 0.0351(4) Uani 1 1 d . . . . .
H24A H 1.002522 0.599258 0.295184 0.042 Uiso 1 1 calc R U . . .
C25 C 0.87529(15) 0.4056(4) 0.31336(13) 0.0326(4) Uani 1 1 d . . . . .
H25A H 0.886926 0.280275 0.268407 0.039 Uiso 1 1 calc R U . . .
C26 C 0.78909(13) 0.3982(4) 0.36281(12) 0.0250(4) Uani 1 1 d . . . . .
H26A H 0.742400 0.267502 0.351085 0.030 Uiso 1 1 calc R U . . .
C31 C 0.36373(12) 0.4021(3) 0.04585(11) 0.0226(3) Uani 1 1 d . . . . .
C32 C 0.37769(13) 0.5906(4) -0.01810(12) 0.0287(4) Uani 1 1 d . . . . .
H32A H 0.424055 0.717769 0.001778 0.034 Uiso 1 1 calc R U . . .
C33 C 0.32378(15) 0.5943(4) -0.11171(13) 0.0342(4) Uani 1 1 d . . . . .
H33A H 0.334082 0.722711 -0.155703 0.041 Uiso 1 1 calc R U . . .
C34 C 0.25551(14) 0.4110(4) -0.14021(12) 0.0337(4) Uani 1 1 d . . . . .
H34A H 0.218557 0.413978 -0.203736 0.040 Uiso 1 1 calc R U . . .
C35 C 0.24078(15) 0.2231(4) -0.07653(14) 0.0347(4) Uani 1 1 d . . . . .
H35A H 0.193395 0.097891 -0.096244 0.042 Uiso 1 1 calc R U . . .
C36 C 0.29510(14) 0.2170(4) 0.01618(13) 0.0298(4) Uani 1 1 d . . . . .
H36A H 0.285481 0.086564 0.059449 0.036 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
O C8 1.215(2) . ?
C1 C11 1.512(2) . ?
C1 C2 1.529(2) . ?
C2 C3 1.5412(19) . ?
C3 C21 1.520(2) . ?
C3 C4 1.539(2) . ?
C4 C5 1.535(2) . ?
C5 C6 1.520(3) . ?
C6 C7 1.527(2) . ?
C7 C8 1.507(3) . ?
C8 C31 1.504(2) . ?
C11 C12 1.391(3) . ?
C11 C16 1.392(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.382(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.393(2) . ?
C21 C26 1.389(2) . ?
C21 C22 1.394(3) . ?
C22 C23 1.392(3) . ?
C23 C24 1.386(3) . ?
C24 C25 1.378(3) . ?
C25 C26 1.391(2) . ?
C31 C32 1.386(3) . ?
C31 C36 1.394(3) . ?
C32 C33 1.397(2) . ?
C33 C34 1.381(3) . ?
C34 C35 1.383(3) . ?
C35 C36 1.389(2) . ?

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 C1 C2 114.36(14) . . ?
C1 C2 C3 112.44(14) . . ?
C21 C3 C4 111.64(14) . . ?
C21 C3 C2 111.03(12) . . ?
C4 C3 C2 110.42(13) . . ?
C5 C4 C3 114.78(13) . . ?
C6 C5 C4 113.33(14) . . ?
C5 C6 C7 113.08(15) . . ?
C8 C7 C6 112.53(15) . . ?
O C8 C31 119.59(16) . . ?
O C8 C7 121.14(14) . . ?
C31 C8 C7 119.25(15) . . ?
C12 C11 C16 118.36(15) . . ?
C12 C11 C1 120.25(15) . . ?
C16 C11 C1 121.30(16) . . ?
C13 C12 C11 120.85(16) . . ?
C14 C13 C12 120.36(17) . . ?
C13 C14 C15 119.61(15) . . ?
C14 C15 C16 119.95(17) . . ?
C11 C16 C15 120.86(17) . . ?
C26 C21 C22 117.99(15) . . ?
C26 C21 C3 120.98(15) . . ?
C22 C21 C3 121.03(15) . . ?
C23 C22 C21 120.96(17) . . ?
C24 C23 C22 120.14(18) . . ?
C25 C24 C23 119.47(16) . . ?
C24 C25 C26 120.32(18) . . ?
C21 C26 C25 121.12(17) . . ?
C32 C31 C36 119.47(15) . . ?
C32 C31 C8 122.70(16) . . ?
C36 C31 C8 117.81(16) . . ?
C31 C32 C33 120.20(17) . . ?
C34 C33 C32 119.92(18) . . ?
C33 C34 C35 120.17(16) . . ?
C34 C35 C36 120.15(18) . . ?
C35 C36 C31 120.10(18) . . ?

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
C11 C1 C2 C3 164.33(14) . . . . ?
C1 C2 C3 C21 -61.43(19) . . . . ?
C1 C2 C3 C4 174.19(14) . . . . ?
C21 C3 C4 C5 54.63(18) . . . . ?
C2 C3 C4 C5 178.66(15) . . . . ?
C3 C4 C5 C6 61.92(19) . . . . ?
C4 C5 C6 C7 177.02(14) . . . . ?
C5 C6 C7 C8 -179.38(14) . . . . ?
C6 C7 C8 O -7.0(2) . . . . ?
C6 C7 C8 C31 171.33(14) . . . . ?
C2 C1 C11 C12 -58.2(2) . . . . ?
C2 C1 C11 C16 125.26(17) . . . . ?
C16 C11 C12 C13 0.6(2) . . . . ?
C1 C11 C12 C13 -176.01(16) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
C1 C11 C16 C15 176.56(16) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
C4 C3 C21 C26 -114.39(17) . . . . ?
C2 C3 C21 C26 121.92(16) . . . . ?
C4 C3 C21 C22 65.76(18) . . . . ?
C2 C3 C21 C22 -57.9(2) . . . . ?
C26 C21 C22 C23 0.1(2) . . . . ?
C3 C21 C22 C23 179.90(16) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C22 C21 C26 C25 -0.1(2) . . . . ?
C3 C21 C26 C25 180.00(16) . . . . ?
C24 C25 C26 C21 -0.1(3) . . . . ?
O C8 C31 C32 -171.33(17) . . . . ?
C7 C8 C31 C32 10.4(2) . . . . ?
O C8 C31 C36 10.3(2) . . . . ?
C7 C8 C31 C36 -167.99(15) . . . . ?
C36 C31 C32 C33 -0.3(3) . . . . ?
C8 C31 C32 C33 -178.67(17) . . . . ?
C31 C32 C33 C34 0.8(3) . . . . ?
C32 C33 C34 C35 -0.4(3) . . . . ?
C33 C34 C35 C36 -0.4(3) . . . . ?
C34 C35 C36 C31 0.8(3) . . . . ?
C32 C31 C36 C35 -0.4(3) . . . . ?
C8 C31 C36 C35 177.96(16) . . . . ?

_refine_diff_density_max         0.143
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030



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