# 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. 
# 
#######################################################################

data_cu_wd20231123_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2401096'
loop_
_audit_author_name
_audit_author_address
'DE WANG'
;Ocean University of China
China
;
_audit_update_record             
;
2024-11-07 deposited with the CCDC.	2025-08-18 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V85 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        'WD-ZFF-Chiral P'
_chemical_name_common            ?
_chemical_formula_sum            'C26 H27 O3 P'
_chemical_formula_moiety         ?
_chemical_formula_weight         418.44
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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                   6.7223(2)
_cell_length_b                   9.4163(3)
_cell_length_c                   36.3295(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2299.63(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9844
_cell_measurement_theta_min      4.8515
_cell_measurement_theta_max      68.082
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6069
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
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   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          ?
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_voltage           50.0
_diffrn_source_current           1.2
_diffrn_detector                 ?
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            28512
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_theta_min         2.432
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4181
_reflns_number_gt                3944
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997
_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 BIS V6.2.15/2021-03-15 && APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0591P)²+0.0776P] 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         4181
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.062(7)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'
P P 0.2955 0.4335 '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
P1 P 0.84881(7) 0.67142(6) 0.60887(2) 0.04524(15) Uani 1 1 d . . . . .
O1 O 0.5811(3) 1.0497(3) 0.69279(8) 0.0861(7) Uani 1 1 d . . . . .
O2 O 1.0643(2) 0.7016(2) 0.60457(5) 0.0609(4) Uani 1 1 d . . . . .
O3 O 0.4232(4) 0.8478(3) 0.68638(10) 0.1246(13) Uani 1 1 d . . . . .
C1 C 0.8509(4) 0.6061(2) 0.68310(5) 0.0497(5) Uani 1 1 d . . . . .
C2 C 1.0424(4) 0.6302(3) 0.69520(7) 0.0618(6) Uani 1 1 d . . . . .
H2 H 1.112917 0.707604 0.686125 0.074 Uiso 1 1 calc R U . . .
C3 C 1.1317(5) 0.5407(4) 0.72073(9) 0.0776(8) Uani 1 1 d . . . . .
H3 H 1.260652 0.558863 0.728705 0.093 Uiso 1 1 calc R U . . .
C4 C 1.0300(6) 0.4255(4) 0.73421(8) 0.0839(9) Uani 1 1 d . . . . .
H4 H 1.088781 0.365706 0.751438 0.101 Uiso 1 1 calc R U . . .
C5 C 0.8409(7) 0.3998(4) 0.72195(10) 0.0940(11) Uani 1 1 d . . . . .
H5 H 0.772195 0.320830 0.730611 0.113 Uiso 1 1 calc R U . . .
C6 C 0.7502(5) 0.4898(3) 0.69675(9) 0.0756(8) Uani 1 1 d . . . . .
H6 H 0.620822 0.471610 0.689032 0.091 Uiso 1 1 calc R U . . .
C7 C 0.7494(3) 0.7032(2) 0.65540(5) 0.0460(4) Uani 1 1 d . . . . .
H7 H 0.608817 0.675776 0.654839 0.055 Uiso 1 1 calc R U . . .
C8 C 0.7954(3) 0.4861(2) 0.59989(5) 0.0493(5) Uani 1 1 d . . . . .
C9 C 0.6047(4) 0.4384(3) 0.59150(7) 0.0625(6) Uani 1 1 d . . . . .
H9 H 0.498754 0.501829 0.590547 0.075 Uiso 1 1 calc R U . . .
C10 C 0.5745(5) 0.2951(3) 0.58456(9) 0.0806(9) Uani 1 1 d . . . . .
H10 H 0.447988 0.262506 0.578590 0.097 Uiso 1 1 calc R U . . .
C11 C 0.7311(6) 0.2007(3) 0.58647(9) 0.0864(10) Uani 1 1 d . . . . .
H11 H 0.709481 0.104451 0.582345 0.104 Uiso 1 1 calc R U . . .
C12 C 0.9183(6) 0.2488(4) 0.59446(11) 0.0874(10) Uani 1 1 d . . . . .
H12 H 1.023965 0.185158 0.595326 0.105 Uiso 1 1 calc R U . . .
C13 C 0.9517(4) 0.3916(3) 0.60125(8) 0.0678(6) Uani 1 1 d . . . . .
H13 H 1.079234 0.423600 0.606705 0.081 Uiso 1 1 calc R U . . .
C14 C 0.7558(3) 0.8596(2) 0.66548(6) 0.0507(5) Uani 1 1 d . . . . .
C15 C 0.5709(4) 0.9148(3) 0.68280(8) 0.0638(6) Uani 1 1 d . . . . .
C16 C 0.3987(6) 1.1227(4) 0.70327(12) 0.0947(11) Uani 1 1 d . . . . .
H16A H 0.426144 1.189680 0.722912 0.114 Uiso 1 1 calc R U . . .
H16B H 0.301985 1.054401 0.712191 0.114 Uiso 1 1 calc R U . . .
C17 C 0.3170(6) 1.1992(5) 0.67084(14) 0.1035(12) Uani 1 1 d . . . . .
H17A H 0.412883 1.266988 0.662207 0.155 Uiso 1 1 calc R U . . .
H17B H 0.197014 1.247600 0.677741 0.155 Uiso 1 1 calc R U . . .
H17C H 0.288377 1.132287 0.651607 0.155 Uiso 1 1 calc R U . . .
C18 C 0.6946(3) 0.7753(2) 0.57822(6) 0.0469(4) Uani 1 1 d . . . . .
C19 C 0.7810(3) 0.8239(3) 0.54558(6) 0.0504(5) Uani 1 1 d . . . . .
H19 H 0.912165 0.799781 0.540365 0.060 Uiso 1 1 calc R U . . .
C20 C 0.6757(4) 0.9074(2) 0.52063(6) 0.0542(5) Uani 1 1 d . . . . .
C21 C 0.4792(4) 0.9457(3) 0.52886(7) 0.0570(5) Uani 1 1 d . . . . .
C22 C 0.3931(4) 0.8944(3) 0.56090(7) 0.0593(6) Uani 1 1 d . . . . .
H22 H 0.261621 0.917429 0.566119 0.071 Uiso 1 1 calc R U . . .
C23 C 0.4980(3) 0.8094(3) 0.58541(6) 0.0537(5) Uani 1 1 d . . . . .
H23 H 0.436290 0.775435 0.606574 0.064 Uiso 1 1 calc R U . . .
C24 C 0.9085(4) 0.9447(3) 0.65972(9) 0.0689(7) Uani 1 1 d . . . . .
H24A H 0.900958 1.039785 0.666509 0.083 Uiso 1 1 calc R U . . .
H24B H 1.023828 0.909622 0.648878 0.083 Uiso 1 1 calc R U . . .
C25 C 0.7761(5) 0.9567(4) 0.48570(8) 0.0767(8) Uani 1 1 d . . . . .
H25A H 0.905723 0.914495 0.483961 0.115 Uiso 1 1 calc R U . . .
H25B H 0.788715 1.058271 0.486100 0.115 Uiso 1 1 calc R U . . .
H25C H 0.697619 0.928805 0.464842 0.115 Uiso 1 1 calc R U . . .
C26 C 0.3617(6) 1.0418(4) 0.50389(9) 0.0833(8) Uani 1 1 d . . . . .
H26A H 0.343782 0.996457 0.480454 0.125 Uiso 1 1 calc R U . . .
H26B H 0.432353 1.129483 0.500569 0.125 Uiso 1 1 calc R U . . .
H26C H 0.234182 1.060729 0.514706 0.125 Uiso 1 1 calc R U . . .


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
P1 O2 1.4842(15) . ?
P1 C18 1.809(2) . ?
P1 C8 1.811(2) . ?
P1 C7 1.842(2) . ?
O1 C15 1.323(4) . ?
O1 C16 1.456(4) . ?
O3 C15 1.183(4) . ?
C1 C2 1.379(4) . ?
C1 C6 1.379(3) . ?
C1 C7 1.521(3) . ?
C2 C3 1.390(4) . ?
C3 C4 1.372(5) . ?
C4 C5 1.368(6) . ?
C5 C6 1.389(5) . ?
C7 C14 1.518(3) . ?
C8 C13 1.378(4) . ?
C8 C9 1.392(3) . ?
C9 C10 1.388(4) . ?
C10 C11 1.379(5) . ?
C11 C12 1.369(5) . ?
C12 C13 1.385(4) . ?
C14 C24 1.319(4) . ?
C14 C15 1.487(4) . ?
C16 C17 1.486(6) . ?
C18 C23 1.385(3) . ?
C18 C19 1.397(3) . ?
C19 C20 1.393(3) . ?
C20 C21 1.402(4) . ?
C20 C25 1.511(3) . ?
C21 C22 1.387(4) . ?
C21 C26 1.505(4) . ?
C22 C23 1.389(4) . ?

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 P1 C18 113.00(10) . . ?
O2 P1 C8 111.05(11) . . ?
C18 P1 C8 107.26(10) . . ?
O2 P1 C7 114.80(10) . . ?
C18 P1 C7 105.61(10) . . ?
C8 P1 C7 104.47(9) . . ?
C15 O1 C16 118.7(3) . . ?
C2 C1 C6 118.3(2) . . ?
C2 C1 C7 122.0(2) . . ?
C6 C1 C7 119.7(2) . . ?
C1 C2 C3 121.1(3) . . ?
C4 C3 C2 120.2(3) . . ?
C5 C4 C3 119.1(3) . . ?
C4 C5 C6 120.9(3) . . ?
C1 C6 C5 120.4(3) . . ?
C14 C7 C1 114.26(17) . . ?
C14 C7 P1 111.64(14) . . ?
C1 C7 P1 110.29(15) . . ?
C13 C8 C9 120.1(2) . . ?
C13 C8 P1 117.66(19) . . ?
C9 C8 P1 122.20(19) . . ?
C10 C9 C8 119.2(3) . . ?
C11 C10 C9 120.4(3) . . ?
C12 C11 C10 119.9(3) . . ?
C11 C12 C13 120.5(3) . . ?
C8 C13 C12 119.8(3) . . ?
C24 C14 C15 120.4(2) . . ?
C24 C14 C7 125.0(2) . . ?
C15 C14 C7 114.68(19) . . ?
O3 C15 O1 121.7(3) . . ?
O3 C15 C14 124.2(3) . . ?
O1 C15 C14 114.1(2) . . ?
O1 C16 C17 109.4(3) . . ?
C23 C18 C19 118.7(2) . . ?
C23 C18 P1 123.78(16) . . ?
C19 C18 P1 117.47(17) . . ?
C20 C19 C18 121.7(2) . . ?
C19 C20 C21 119.1(2) . . ?
C19 C20 C25 119.6(2) . . ?
C21 C20 C25 121.4(2) . . ?
C22 C21 C20 118.8(2) . . ?
C22 C21 C26 119.8(3) . . ?
C20 C21 C26 121.4(2) . . ?
C21 C22 C23 121.8(2) . . ?
C18 C23 C22 119.8(2) . . ?

