# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
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data_a
_audit_block_doi                 10.5517/ccdc.csd.cc2gqr65
_database_code_depnum_ccdc_archive 'CCDC 2285977'
loop_
_audit_author_name
_audit_author_address
'Fengqian Zhao'
;zhengzhou university
China
;
_audit_update_record             
;
2023-08-01 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_audit_creation_date             2023-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 O2 P'
_chemical_formula_sum            'C21 H19 O2 P'
_chemical_formula_weight         334.33
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.242(18)
_cell_length_b                   8.394(4)
_cell_length_c                   17.127(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.39(4)
_cell_angle_gamma                90
_cell_volume                     3438(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6689
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.717
_cell_measurement_theta_min      2.410
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1592 before and 0.0791 after correction. The Ratio of minimum to maximum transmission is 0.8159. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6083
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36386
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.411
_diffrn_ambient_temperature      292.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2698
_reflns_number_total             3517
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+1.6594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1081
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C16(H16), C17(H17), C19(H19), C20(H20)
2.b X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C1 C 0.40622(7) 0.29582(19) 0.29112(10) 0.0356(4) Uani 1 1 d . . . . .
C2 C 0.45716(8) 0.3118(2) 0.34019(13) 0.0523(5) Uani 1 1 d . . . . .
H2 H 0.4784 0.2222 0.3569 0.063 Uiso 1 1 calc R . . . .
C3 C 0.47633(9) 0.4619(3) 0.36420(16) 0.0698(7) Uani 1 1 d . . . . .
H3 H 0.5105 0.4727 0.3975 0.084 Uiso 1 1 calc R . . . .
C4 C 0.44564(9) 0.5951(2) 0.33949(14) 0.0601(6) Uani 1 1 d . . . . .
H4 H 0.4594 0.6957 0.3550 0.072 Uiso 1 1 calc R . . . .
C5 C 0.39489(9) 0.5798(2) 0.29208(13) 0.0509(5) Uani 1 1 d . . . . .
H5 H 0.3737 0.6699 0.2760 0.061 Uiso 1 1 calc R . . . .
C6 C 0.37497(8) 0.4308(2) 0.26806(11) 0.0429(4) Uani 1 1 d . . . . .
H6 H 0.3402 0.4210 0.2361 0.052 Uiso 1 1 calc R . . . .
C7 C 0.40343(7) 0.0879(2) 0.15734(11) 0.0392(4) Uani 1 1 d . . . . .
C8 C 0.42772(8) -0.0524(2) 0.13630(12) 0.0483(5) Uani 1 1 d . . . . .
H8 H 0.4356 -0.1341 0.1731 0.058 Uiso 1 1 calc R . . . .
C9 C 0.44005(9) -0.0705(3) 0.06117(13) 0.0578(6) Uani 1 1 d . . . . .
H9 H 0.4561 -0.1648 0.0473 0.069 Uiso 1 1 calc R . . . .
C10 C 0.42880(9) 0.0494(3) 0.00656(13) 0.0594(6) Uani 1 1 d . . . . .
H10 H 0.4367 0.0359 -0.0444 0.071 Uiso 1 1 calc R . . . .
C11 C 0.40579(9) 0.1896(3) 0.02733(12) 0.0560(5) Uani 1 1 d . . . . .
H11 H 0.3985 0.2714 -0.0095 0.067 Uiso 1 1 calc R . . . .
C12 C 0.39349(8) 0.2096(2) 0.10220(11) 0.0479(5) Uani 1 1 d . . . . .
H12 H 0.3784 0.3054 0.1160 0.057 Uiso 1 1 calc R . . . .
C13 C 0.31009(7) 0.09576(19) 0.24336(10) 0.0368(4) Uani 1 1 d . . . . .
C14 C 0.27878(8) 0.1022(2) 0.17281(12) 0.0492(5) Uani 1 1 d . . . . .
H14A H 0.2400 0.0988 0.1681 0.059 Uiso 1 1 calc R . . . .
H14B H 0.2954 0.1100 0.1278 0.059 Uiso 1 1 calc R . . . .
C15 C 0.28400(7) 0.08321(19) 0.31570(10) 0.0358(4) Uani 1 1 d . . . . .
C16 C 0.29870(8) -0.0356(2) 0.37177(11) 0.0424(4) Uani 1 1 d . . . . .
H16 H 0.3283 -0.1035 0.3671 0.051 Uiso 1 1 calc R . . . .
C17 C 0.26999(8) -0.0539(2) 0.43416(12) 0.0475(5) Uani 1 1 d . . . . .
H17 H 0.2799 -0.1353 0.4706 0.057 Uiso 1 1 calc R . . . .
C18 C 0.22643(8) 0.0479(2) 0.44335(11) 0.0434(5) Uani 1 1 d . . . . .
C19 C 0.21263(8) 0.1703(2) 0.39000(12) 0.0467(5) Uani 1 1 d . . . . .
H19 H 0.1844 0.2416 0.3965 0.056 Uiso 1 1 calc R . . . .
C20 C 0.24110(8) 0.1861(2) 0.32706(11) 0.0432(4) Uani 1 1 d . . . . .
H20 H 0.2313 0.2683 0.2910 0.052 Uiso 1 1 calc R . . . .
C21 C 0.15505(10) 0.1175(3) 0.51773(15) 0.0671(7) Uani 1 1 d . . . . .
H21A H 0.1262 0.1122 0.4722 0.101 Uiso 1 1 calc GR . . . .
H21B H 0.1682 0.2252 0.5252 0.101 Uiso 1 1 calc GR . . . .
H21C H 0.1403 0.0832 0.5637 0.101 Uiso 1 1 calc GR . . . .
O1 O 0.41278(5) -0.02907(14) 0.30694(7) 0.0445(3) Uani 1 1 d . . . . .
O2 O 0.20012(6) 0.01663(18) 0.50615(8) 0.0585(4) Uani 1 1 d . . . . .
P1 P 0.38583(2) 0.09931(5) 0.25522(3) 0.03467(16) Uani 1 1 d . . . . .


_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
C1 C2 1.382(3) . ?
C1 C6 1.384(2) . ?
C1 P1 1.8010(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(3) . ?
C7 C12 1.385(3) . ?
C7 P1 1.799(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.319(3) . ?
C13 C15 1.484(3) . ?
C13 P1 1.814(2) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C15 C16 1.390(2) . ?
C15 C20 1.390(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(3) . ?
C18 C19 1.379(3) . ?
C18 O2 1.363(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 O2 1.421(3) . ?
O1 P1 1.4778(14) . ?

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
C2 C1 C6 119.13(16) . . ?
C2 C1 P1 117.70(13) . . ?
C6 C1 P1 123.05(14) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.57(18) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.87(18) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.03(18) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.57(17) . . ?
C5 C6 H6 119.7 . . ?
C8 C7 P1 117.52(15) . . ?
C12 C7 C8 118.79(19) . . ?
C12 C7 P1 123.69(15) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C15 120.51(18) . . ?
C14 C13 P1 121.50(16) . . ?
C15 C13 P1 117.98(13) . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C16 C15 C13 122.12(16) . . ?
C16 C15 C20 117.55(17) . . ?
C20 C15 C13 120.23(16) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.76(18) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.70(18) . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.36(18) . . ?
O2 C18 C17 115.73(17) . . ?
O2 C18 C19 124.91(18) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.47(18) . . ?
C20 C19 H19 120.3 . . ?
C15 C20 H20 119.0 . . ?
C19 C20 C15 122.09(17) . . ?
C19 C20 H20 119.0 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
C18 O2 C21 117.71(17) . . ?
C1 P1 C13 105.64(8) . . ?
C7 P1 C1 105.87(8) . . ?
C7 P1 C13 106.53(9) . . ?
O1 P1 C1 113.16(9) . . ?
O1 P1 C7 111.76(9) . . ?
O1 P1 C13 113.30(8) . . ?

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
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C2 C1 P1 C7 -98.13(17) . . . . ?
C2 C1 P1 C13 149.11(16) . . . . ?
C2 C1 P1 O1 24.60(18) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C6 C1 P1 C7 77.89(18) . . . . ?
C6 C1 P1 C13 -34.87(18) . . . . ?
C6 C1 P1 O1 -159.38(15) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C7 C12 C11 2.1(3) . . . . ?
C8 C7 P1 C1 137.97(15) . . . . ?
C8 C7 P1 C13 -109.90(15) . . . . ?
C8 C7 P1 O1 14.35(17) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C7 -0.9(3) . . . . ?
C12 C7 C8 C9 -1.8(3) . . . . ?
C12 C7 P1 C1 -42.87(18) . . . . ?
C12 C7 P1 C13 69.26(17) . . . . ?
C12 C7 P1 O1 -166.49(15) . . . . ?
C13 C15 C16 C17 -173.52(17) . . . . ?
C13 C15 C20 C19 174.54(16) . . . . ?
C14 C13 C15 C16 126.8(2) . . . . ?
C14 C13 C15 C20 -49.4(2) . . . . ?
C14 C13 P1 C1 105.50(16) . . . . ?
C14 C13 P1 C7 -6.79(17) . . . . ?
C14 C13 P1 O1 -130.08(15) . . . . ?
C15 C13 P1 C1 -75.29(14) . . . . ?
C15 C13 P1 C7 172.42(12) . . . . ?
C15 C13 P1 O1 49.12(15) . . . . ?
C15 C16 C17 C18 -1.3(3) . . . . ?
C16 C15 C20 C19 -1.8(3) . . . . ?
C16 C17 C18 C19 -1.2(3) . . . . ?
C16 C17 C18 O2 178.57(17) . . . . ?
C17 C18 C19 C20 2.2(3) . . . . ?
C17 C18 O2 C21 -179.76(18) . . . . ?
C18 C19 C20 C15 -0.7(3) . . . . ?
C19 C18 O2 C21 0.0(3) . . . . ?
C20 C15 C16 C17 2.7(3) . . . . ?
O2 C18 C19 C20 -177.61(17) . . . . ?
P1 C1 C2 C3 175.11(18) . . . . ?
P1 C1 C6 C5 -174.42(16) . . . . ?
P1 C7 C8 C9 177.41(15) . . . . ?
P1 C7 C12 C11 -177.07(15) . . . . ?
P1 C13 C15 C16 -52.5(2) . . . . ?
P1 C13 C15 C20 131.40(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
