# 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_shx97
_database_code_depnum_ccdc_archive 'CCDC 2392956'
loop_
_audit_author_name
_audit_author_address
'Jie-Ping Wan'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2024-10-22 deposited with the CCDC.	2024-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 O3 P'
_chemical_formula_sum            'C21 H19 O3 P'
_chemical_formula_weight         350.33

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.5836(19)
_cell_length_b                   10.090(2)
_cell_length_c                   10.318(2)
_cell_angle_alpha                82.92(3)
_cell_angle_beta                 78.03(3)
_cell_angle_gamma                65.49(3)
_cell_volume                     887.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5702
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.38
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7062
_diffrn_reflns_av_unetI/netI     0.0968
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.064
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3121
_reflns_number_gt                2074
_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       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0515P)²] 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         3121
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_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
P1 P 0.33855(7) 0.17432(6) 0.68649(7) 0.0492(3) Uani 1 1 d . . . . .
O1 O 0.5308(2) 0.4154(2) 0.3405(3) 0.0886(8) Uani 1 1 d . . . . .
O2 O 0.35628(18) 0.22669(17) 0.43037(18) 0.0560(5) Uani 1 1 d . . . . .
H2B H 0.426913 0.153342 0.397448 0.084 Uiso 1 1 calc R U . . .
O3 O 0.4152(2) 0.01303(16) 0.67915(19) 0.0633(6) Uani 1 1 d . . . . .
C1 C 0.8378(4) 0.2750(3) 0.2004(3) 0.0789(10) Uani 1 1 d . . . . .
H1A H 0.762305 0.311425 0.146367 0.095 Uiso 1 1 calc R U . . .
C2 C 0.9924(5) 0.2381(4) 0.1442(5) 0.1011(15) Uani 1 1 d . . . . .
H2A H 1.021564 0.246618 0.052830 0.121 Uiso 1 1 calc R U . . .
C3 C 1.1022(5) 0.1890(4) 0.2250(6) 0.1018(17) Uani 1 1 d . . . . .
H3A H 1.205500 0.170068 0.188571 0.122 Uiso 1 1 calc R U . . .
C4 C 1.0618(4) 0.1672(4) 0.3585(5) 0.0930(13) Uani 1 1 d . . . . .
H4A H 1.137414 0.131106 0.412327 0.112 Uiso 1 1 calc R U . . .
C5 C 0.9069(4) 0.1997(3) 0.4126(4) 0.0723(9) Uani 1 1 d . . . . .
H5A H 0.879585 0.181123 0.502706 0.087 Uiso 1 1 calc R U . . .
C6 C 0.7936(3) 0.2587(3) 0.3355(3) 0.0547(7) Uani 1 1 d . . . . .
C7 C 0.6246(3) 0.3111(3) 0.3907(3) 0.0596(8) Uani 1 1 d . . . . .
C8 C 0.5739(3) 0.2321(3) 0.5146(3) 0.0552(7) Uani 1 1 d . . . . .
H8A H 0.632236 0.127831 0.506535 0.066 Uiso 1 1 calc R U . . .
H8B H 0.597713 0.260385 0.591117 0.066 Uiso 1 1 calc R U . . .
C9 C 0.4021(3) 0.2663(2) 0.5361(3) 0.0499(7) Uani 1 1 d . . . . .
H9A H 0.345093 0.371718 0.545656 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3772(3) 0.2335(3) 0.8274(3) 0.0526(7) Uani 1 1 d . . . . .
C11 C 0.5037(4) 0.1456(4) 0.8832(4) 0.0919(12) Uani 1 1 d . . . . .
H11A H 0.571007 0.057247 0.845610 0.110 Uiso 1 1 calc R U . . .
C12 C 0.5339(4) 0.1856(5) 0.9948(4) 0.0988(12) Uani 1 1 d . . . . .
H12A H 0.620939 0.123499 1.030888 0.119 Uiso 1 1 calc R U . . .
C13 C 0.4394(5) 0.3126(4) 1.0519(4) 0.0840(11) Uani 1 1 d . . . . .
H13A H 0.459237 0.339099 1.127079 0.101 Uiso 1 1 calc R U . . .
C14 C 0.3165(6) 0.3989(4) 0.9967(4) 0.1126(15) Uani 1 1 d . . . . .
H14A H 0.251292 0.487666 1.034519 0.135 Uiso 1 1 calc R U . . .
C15 C 0.2808(4) 0.3629(3) 0.8854(4) 0.0890(11) Uani 1 1 d . . . . .
H15A H 0.192794 0.425727 0.850878 0.107 Uiso 1 1 calc R U . . .
C16 C 0.1301(3) 0.2412(2) 0.7051(3) 0.0504(7) Uani 1 1 d . . . . .
C17 C 0.0606(3) 0.1470(3) 0.7611(3) 0.0599(8) Uani 1 1 d . . . . .
H17A H 0.121768 0.051190 0.783860 0.072 Uiso 1 1 calc R U . . .
C18 C -0.1006(4) 0.1952(3) 0.7834(3) 0.0749(10) Uani 1 1 d . . . . .
H18A H -0.146582 0.131204 0.821149 0.090 Uiso 1 1 calc R U . . .
C19 C -0.1916(3) 0.3346(3) 0.7506(3) 0.0702(9) Uani 1 1 d . . . . .
H19A H -0.299349 0.366286 0.768201 0.084 Uiso 1 1 calc R U . . .
C20 C -0.1253(3) 0.4292(3) 0.6915(3) 0.0693(9) Uani 1 1 d . . . . .
H20A H -0.187629 0.523719 0.666125 0.083 Uiso 1 1 calc R U . . .
C21 C 0.0355(3) 0.3828(3) 0.6698(3) 0.0599(8) Uani 1 1 d . . . . .
H21A H 0.080376 0.447355 0.631296 0.072 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
P1 O3 1.4863(16) . ?
P1 C10 1.797(3) . ?
P1 C16 1.799(3) . ?
P1 C9 1.833(3) . ?
O1 C7 1.207(4) . ?
O2 C9 1.413(3) . ?
O2 H2B 0.8200 . ?
C1 C6 1.381(4) . ?
C1 C2 1.382(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.370(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.367(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.368(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.486(4) . ?
C7 C8 1.523(4) . ?
C8 C9 1.509(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9800 . ?
C10 C11 1.364(5) . ?
C10 C15 1.371(4) . ?
C11 C12 1.387(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.346(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.332(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.392(5) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.383(3) . ?
C16 C21 1.389(4) . ?
C17 C18 1.390(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.357(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.373(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.388(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?

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
O3 P1 C10 111.06(13) . . ?
O3 P1 C16 112.19(10) . . ?
C10 P1 C16 106.18(12) . . ?
O3 P1 C9 111.93(10) . . ?
C10 P1 C9 108.89(11) . . ?
C16 P1 C9 106.30(13) . . ?
C9 O2 H2B 109.5 . . ?
C6 C1 C2 121.0(4) . . ?
C6 C1 H1A 119.5 . . ?
C2 C1 H1A 119.5 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 123.2(3) . . ?
C1 C6 C7 118.2(3) . . ?
O1 C7 C6 120.9(3) . . ?
O1 C7 C8 121.1(2) . . ?
C6 C7 C8 118.0(3) . . ?
C9 C8 C7 111.9(3) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O2 C9 C8 113.44(18) . . ?
O2 C9 P1 106.60(15) . . ?
C8 C9 P1 112.5(2) . . ?
O2 C9 H9A 108.1 . . ?
C8 C9 H9A 108.1 . . ?
P1 C9 H9A 108.1 . . ?
C11 C10 C15 117.7(3) . . ?
C11 C10 P1 119.7(2) . . ?
C15 C10 P1 122.5(3) . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C14 C13 C12 117.6(4) . . ?
C14 C13 H13A 121.2 . . ?
C12 C13 H13A 121.2 . . ?
C13 C14 C15 123.2(3) . . ?
C13 C14 H14A 118.4 . . ?
C15 C14 H14A 118.4 . . ?
C10 C15 C14 119.0(4) . . ?
C10 C15 H15A 120.5 . . ?
C14 C15 H15A 120.5 . . ?
C17 C16 C21 118.4(2) . . ?
C17 C16 P1 117.8(2) . . ?
C21 C16 P1 123.71(18) . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21A 119.6 . . ?
C16 C21 H21A 119.6 . . ?

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
C6 C1 C2 C3 -2.0(5) . . . . ?
C1 C2 C3 C4 4.2(6) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C3 C4 C5 C6 -2.8(4) . . . . ?
C4 C5 C6 C1 4.9(4) . . . . ?
C4 C5 C6 C7 -172.8(2) . . . . ?
C2 C1 C6 C5 -2.5(4) . . . . ?
C2 C1 C6 C7 175.3(3) . . . . ?
C5 C6 C7 O1 145.5(3) . . . . ?
C1 C6 C7 O1 -32.2(4) . . . . ?
C5 C6 C7 C8 -32.7(3) . . . . ?
C1 C6 C7 C8 149.6(3) . . . . ?
O1 C7 C8 C9 18.4(4) . . . . ?
C6 C7 C8 C9 -163.4(2) . . . . ?
C7 C8 C9 O2 59.9(3) . . . . ?
C7 C8 C9 P1 -179.08(16) . . . . ?
O3 P1 C9 O2 62.12(19) . . . . ?
C10 P1 C9 O2 -174.71(15) . . . . ?
C16 P1 C9 O2 -60.70(16) . . . . ?
O3 P1 C9 C8 -62.79(19) . . . . ?
C10 P1 C9 C8 60.38(18) . . . . ?
C16 P1 C9 C8 174.39(15) . . . . ?
O3 P1 C10 C11 22.0(3) . . . . ?
C16 P1 C10 C11 144.2(3) . . . . ?
C9 P1 C10 C11 -101.7(3) . . . . ?
O3 P1 C10 C15 -155.6(2) . . . . ?
C16 P1 C10 C15 -33.4(3) . . . . ?
C9 P1 C10 C15 80.7(3) . . . . ?
C15 C10 C11 C12 0.1(5) . . . . ?
P1 C10 C11 C12 -177.7(3) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C11 C10 C15 C14 0.4(5) . . . . ?
P1 C10 C15 C14 178.1(3) . . . . ?
C13 C14 C15 C10 -1.0(7) . . . . ?
O3 P1 C16 C17 24.8(3) . . . . ?
C10 P1 C16 C17 -96.7(2) . . . . ?
C9 P1 C16 C17 147.4(2) . . . . ?
O3 P1 C16 C21 -157.1(2) . . . . ?
C10 P1 C16 C21 81.4(3) . . . . ?
C9 P1 C16 C21 -34.4(3) . . . . ?
C21 C16 C17 C18 -1.2(4) . . . . ?
P1 C16 C17 C18 177.0(2) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 1.8(5) . . . . ?
C18 C19 C20 C21 -2.3(5) . . . . ?
C19 C20 C21 C16 1.2(4) . . . . ?
C17 C16 C21 C20 0.6(4) . . . . ?
P1 C16 C21 C20 -177.5(2) . . . . ?

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.054



