# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2070764'
loop_
_audit_author_name
_audit_author_address
songxr
;Jiangxi Science  Technology Normal University
China
;
_audit_update_record             
;
2021-05-26 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 O3 P S'
_chemical_formula_weight         436.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
S S 0.1246 0.1234 '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                   9.7821(15)
_cell_length_b                   10.8018(16)
_cell_length_c                   12.4788(19)
_cell_angle_alpha                106.814(2)
_cell_angle_beta                 97.289(2)
_cell_angle_gamma                108.910(2)
_cell_volume                     1158.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4626
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.71

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   none
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5889
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4044
_reflns_number_gt                3587
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0562P)²+0.3425P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.061(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4044
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
S1 S 0.65112(5) 0.94479(4) 0.31654(3) 0.04287(15) Uani 1 1 d . . . . .
P1 P 0.59482(5) 0.85011(4) 0.13795(3) 0.03728(15) Uani 1 1 d . . . . .
O3 O 0.42151(13) 0.78277(12) 0.09545(10) 0.0434(3) Uani 1 1 d . . . . .
O1 O 0.62507(14) 0.71194(13) 0.10654(11) 0.0499(3) Uani 1 1 d . . . . .
O2 O 0.67426(15) 0.95432(14) 0.09127(11) 0.0522(3) Uani 1 1 d . . . . .
C10 C 0.75267(17) 0.74809(16) 0.58330(13) 0.0349(4) Uani 1 1 d . . . . .
C7 C 0.54158(18) 0.80706(16) 0.36052(13) 0.0356(4) Uani 1 1 d . . . . .
C16 C 0.69649(17) 0.55081(17) 0.38810(13) 0.0360(4) Uani 1 1 d . . . . .
C8 C 0.61249(19) 0.74458(17) 0.40731(13) 0.0382(4) Uani 1 1 d . . . . .
C9 C 0.68467(17) 0.68360(16) 0.45594(13) 0.0350(4) Uani 1 1 d . . . . .
C6 C 0.38006(19) 0.77623(18) 0.34916(13) 0.0403(4) Uani 1 1 d . . . . .
C21 C 0.7597(2) 0.47962(19) 0.44194(16) 0.0469(4) Uani 1 1 d . . . . .
H21 H 0.7975 0.5162 0.5216 0.056 Uiso 1 1 calc R U . . .
C17 C 0.6426(2) 0.49354(19) 0.26872(15) 0.0472(4) Uani 1 1 d . . . . .
H17 H 0.6000 0.5394 0.2307 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3261(2) 0.8833(2) 0.37327(16) 0.0545(5) Uani 1 1 d . . . . .
H5 H 0.3915 0.9756 0.3939 0.065 Uiso 1 1 calc R U . . .
C15 C 0.6640(2) 0.7560(2) 0.66075(15) 0.0472(4) Uani 1 1 d . . . . .
H15 H 0.5611 0.7222 0.6338 0.057 Uiso 1 1 calc R U . . .
C11 C 0.9063(2) 0.8007(2) 0.62535(17) 0.0533(5) Uani 1 1 d . . . . .
H11 H 0.9676 0.7972 0.5743 0.064 Uiso 1 1 calc R U . . .
C20 C 0.7671(2) 0.3547(2) 0.37829(19) 0.0598(5) Uani 1 1 d . . . . .
H20 H 0.8087 0.3076 0.4157 0.072 Uiso 1 1 calc R U . . .
C24 C 0.3383(2) 0.8720(2) 0.08922(18) 0.0562(5) Uani 1 1 d . . . . .
H24A H 0.3684 0.9201 0.0363 0.067 Uiso 1 1 calc R U . . .
H24B H 0.3575 0.9414 0.1648 0.067 Uiso 1 1 calc R U . . .
C1 C 0.2815(2) 0.6391(2) 0.31611(17) 0.0567(5) Uani 1 1 d . . . . .
H1 H 0.3159 0.5665 0.2987 0.068 Uiso 1 1 calc R U . . .
C18 C 0.6517(2) 0.3696(2) 0.20616(17) 0.0577(5) Uani 1 1 d . . . . .
H18 H 0.6155 0.3329 0.1264 0.069 Uiso 1 1 calc R U . . .
C19 C 0.7139(3) 0.2996(2) 0.26090(19) 0.0613(5) Uani 1 1 d . . . . .
H19 H 0.7197 0.2159 0.2185 0.074 Uiso 1 1 calc R U . . .
C12 C 0.9681(2) 0.8583(2) 0.74320(19) 0.0646(6) Uani 1 1 d . . . . .
H12 H 1.0710 0.8934 0.7710 0.078 Uiso 1 1 calc R U . . .
C13 C 0.8793(3) 0.8638(2) 0.81889(18) 0.0659(6) Uani 1 1 d . . . . .
H13 H 0.9218 0.9013 0.8979 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7278(3) 0.8143(2) 0.77884(17) 0.0614(5) Uani 1 1 d . . . . .
H14 H 0.6676 0.8198 0.8306 0.074 Uiso 1 1 calc R U . . .
C2 C 0.1303(3) 0.6104(3) 0.3090(2) 0.0820(8) Uani 1 1 d . . . . .
H2 H 0.0635 0.5184 0.2868 0.098 Uiso 1 1 calc R U . . .
C25 C 0.1769(2) 0.7804(3) 0.0477(2) 0.0769(7) Uani 1 1 d . . . . .
H25A H 0.1591 0.7127 -0.0274 0.115 Uiso 1 1 calc R U . . .
H25B H 0.1192 0.8364 0.0431 0.115 Uiso 1 1 calc R U . . .
H25C H 0.1485 0.7331 0.1005 0.115 Uiso 1 1 calc R U . . .
C22 C 0.7705(2) 0.7135(3) 0.0961(2) 0.0720(6) Uani 1 1 d . . . . .
H22A H 0.8226 0.7102 0.1661 0.086 Uiso 1 1 calc R U . . .
H22B H 0.8281 0.7994 0.0861 0.086 Uiso 1 1 calc R U . . .
C4 C 0.1767(3) 0.8533(4) 0.3666(2) 0.0772(7) Uani 1 1 d . . . . .
H4 H 0.1418 0.9255 0.3840 0.093 Uiso 1 1 calc R U . . .
C3 C 0.0797(3) 0.7185(4) 0.3349(2) 0.0876(9) Uani 1 1 d . . . . .
H3 H -0.0211 0.6991 0.3306 0.105 Uiso 1 1 calc R U . . .
C23 C 0.7571(3) 0.5946(3) -0.0018(3) 0.1029(11) Uani 1 1 d . . . . .
H23A H 0.7120 0.6017 -0.0716 0.154 Uiso 1 1 calc R U . . .
H23B H 0.6961 0.5098 0.0066 0.154 Uiso 1 1 calc R U . . .
H23C H 0.8542 0.5934 -0.0052 0.154 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
S1 C7 1.8031(17) . ?
S1 P1 2.0787(6) . ?
P1 O2 1.4621(13) . ?
P1 O3 1.5600(12) . ?
P1 O1 1.5640(13) . ?
O3 C24 1.460(2) . ?
O1 C22 1.441(3) . ?
C10 C15 1.381(2) . ?
C10 C11 1.390(2) . ?
C10 C9 1.498(2) . ?
C7 C8 1.306(2) . ?
C7 C6 1.484(2) . ?
C16 C21 1.388(2) . ?
C16 C17 1.391(2) . ?
C16 C9 1.489(2) . ?
C8 C9 1.313(2) . ?
C6 C1 1.384(3) . ?
C6 C5 1.393(3) . ?
C21 C20 1.384(3) . ?
C21 H21 0.9300 . ?
C17 C18 1.378(3) . ?
C17 H17 0.9300 . ?
C5 C4 1.377(3) . ?
C5 H5 0.9300 . ?
C15 C14 1.390(3) . ?
C15 H15 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C20 C19 1.368(3) . ?
C20 H20 0.9300 . ?
C24 C25 1.491(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C1 C2 1.394(3) . ?
C1 H1 0.9300 . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C12 C13 1.364(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C22 C23 1.450(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C4 C3 1.361(4) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C7 S1 P1 102.22(5) . . ?
O2 P1 O3 117.37(7) . . ?
O2 P1 O1 116.41(8) . . ?
O3 P1 O1 97.87(7) . . ?
O2 P1 S1 107.42(6) . . ?
O3 P1 S1 108.44(5) . . ?
O1 P1 S1 108.78(5) . . ?
C24 O3 P1 119.37(12) . . ?
C22 O1 P1 120.85(13) . . ?
C15 C10 C11 118.93(16) . . ?
C15 C10 C9 120.67(14) . . ?
C11 C10 C9 120.40(15) . . ?
C8 C7 C6 123.38(15) . . ?
C8 C7 S1 117.05(13) . . ?
C6 C7 S1 119.46(11) . . ?
C21 C16 C17 118.04(16) . . ?
C21 C16 C9 121.15(15) . . ?
C17 C16 C9 120.81(14) . . ?
C7 C8 C9 179.04(17) . . ?
C8 C9 C16 121.54(14) . . ?
C8 C9 C10 118.70(14) . . ?
C16 C9 C10 119.73(13) . . ?
C1 C6 C5 119.36(18) . . ?
C1 C6 C7 119.52(16) . . ?
C5 C6 C7 121.11(17) . . ?
C20 C21 C16 120.65(17) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C18 C17 C16 120.79(17) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C10 C15 C14 120.33(17) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C12 C11 C10 120.04(19) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C19 C20 C21 120.69(18) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
O3 C24 C25 107.58(18) . . ?
O3 C24 H24A 110.2 . . ?
C25 C24 H24A 110.2 . . ?
O3 C24 H24B 110.2 . . ?
C25 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
C6 C1 C2 119.5(2) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C19 C18 C17 120.52(18) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.31(18) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C13 C12 C11 120.51(18) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.18(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 C22 C23 110.1(2) . . ?
O1 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
O1 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
O2 P1 O3 C24 -45.00(15) . . . . ?
O1 P1 O3 C24 -170.25(13) . . . . ?
S1 P1 O3 C24 76.87(13) . . . . ?
O2 P1 O1 C22 35.36(18) . . . . ?
O3 P1 O1 C22 161.30(16) . . . . ?
S1 P1 O1 C22 -86.10(16) . . . . ?
P1 S1 C7 C8 105.91(12) . . . . ?
P1 S1 C7 C6 -77.88(12) . . . . ?
C21 C16 C9 C8 -173.39(17) . . . . ?
C17 C16 C9 C8 5.8(2) . . . . ?
C21 C16 C9 C10 4.9(2) . . . . ?
C17 C16 C9 C10 -175.90(15) . . . . ?
C15 C10 C9 C8 64.8(2) . . . . ?
C11 C10 C9 C8 -115.31(19) . . . . ?
C15 C10 C9 C16 -113.53(18) . . . . ?
C11 C10 C9 C16 66.3(2) . . . . ?
C8 C7 C6 C1 -41.7(2) . . . . ?
S1 C7 C6 C1 142.31(14) . . . . ?
C8 C7 C6 C5 137.09(18) . . . . ?
S1 C7 C6 C5 -38.9(2) . . . . ?
C17 C16 C21 C20 -0.7(3) . . . . ?
C9 C16 C21 C20 178.55(17) . . . . ?
C21 C16 C17 C18 0.1(3) . . . . ?
C9 C16 C17 C18 -179.07(17) . . . . ?
C1 C6 C5 C4 1.4(3) . . . . ?
C7 C6 C5 C4 -177.46(17) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
C9 C10 C15 C14 179.14(17) . . . . ?
C15 C10 C11 C12 0.8(3) . . . . ?
C9 C10 C11 C12 -179.05(17) . . . . ?
C16 C21 C20 C19 0.8(3) . . . . ?
P1 O3 C24 C25 -179.31(14) . . . . ?
C5 C6 C1 C2 -0.9(3) . . . . ?
C7 C6 C1 C2 177.95(17) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C21 C20 C19 C18 -0.4(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C10 C15 C14 C13 -0.2(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
P1 O1 C22 C23 -139.2(2) . . . . ?
C6 C5 C4 C3 -0.9(3) . . . . ?
C5 C4 C3 C2 0.0(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.037

