# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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 
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data_mo_wtl_hhl_diene_2_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2bwxjp
_database_code_depnum_ccdc_archive 'CCDC 2171783'
loop_
_audit_author_name
_audit_author_address
'Hui-Lin Hu'
;Sichuan University
China
;
_audit_update_record             
;
2022-05-10 deposited with the CCDC.	2023-08-03 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C30 H25 O3 P), C H2 Cl2'
_chemical_formula_sum            'C61 H52 Cl2 O6 P2'
_chemical_formula_weight         1013.86
_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'
Cl Cl 0.1484 0.1585 '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                   44.9718(11)
_cell_length_b                   6.84850(10)
_cell_length_c                   18.4695(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.1240(10)
_cell_angle_gamma                90
_cell_volume                     5191.60(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    304(2)
_cell_measurement_theta_max      27.383
_cell_measurement_theta_min      2.417
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1462 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.8676.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2120
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37050
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         1.985
_diffrn_ambient_temperature      304.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4440
_reflns_number_total             5946
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5946
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+5.4897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1387
_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, All O(H) groups
2. Others
 Fixed Sof: H30A(0.5) H30B(0.5)
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C26(H26), C27(H27), C28(H28), C29(H29)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
P1 P 0.58860(2) 0.69717(7) 0.59560(3) 0.03575(14) Uani 1 1 d . . . . .
O1 O 0.58285(4) 0.48793(19) 0.60829(8) 0.0441(3) Uani 1 1 d . . . . .
O2 O 0.65050(4) 0.6458(2) 0.48742(9) 0.0466(4) Uani 1 1 d . . . . .
O3 O 0.62386(3) 0.23849(19) 0.57002(8) 0.0400(3) Uani 1 1 d . . . . .
H3 H 0.6106 0.2801 0.5863 0.060 Uiso 1 1 calc R U . . .
Cl1 Cl 0.53044(3) 0.41386(18) 0.23897(7) 0.1194(4) Uani 1 1 d . . . . .
C32 C 0.66693(5) 0.3323(3) 0.53035(11) 0.0388(4) Uani 1 1 d . . . . .
C1 C 0.73573(8) 0.1816(5) 0.84429(16) 0.0819(9) Uani 1 1 d . . . . .
H1 H 0.7515 0.1156 0.8867 0.098 Uiso 1 1 calc R U . . .
C2 C 0.74174(7) 0.3647(6) 0.82498(17) 0.0812(9) Uani 1 1 d . . . . .
H2 H 0.7617 0.4238 0.8545 0.097 Uiso 1 1 calc R U . . .
C3 C 0.71833(6) 0.4648(4) 0.76136(14) 0.0608(6) Uani 1 1 d . . . . .
H3A H 0.7227 0.5904 0.7491 0.073 Uiso 1 1 calc R U . . .
C4 C 0.68877(5) 0.3782(3) 0.71660(11) 0.0410(4) Uani 1 1 d . . . . .
C5 C 0.66353(5) 0.4843(3) 0.65033(11) 0.0356(4) Uani 1 1 d . . . . .
C6 C 0.65395(5) 0.6669(3) 0.65107(12) 0.0404(4) Uani 1 1 d . . . . .
H6 H 0.6639 0.7513 0.6936 0.048 Uiso 1 1 calc R U . . .
C7 C 0.62531(5) 0.7244(3) 0.57621(11) 0.0381(4) Uani 1 1 d . . . . .
H7 H 0.6276 0.8576 0.5597 0.046 Uiso 1 1 calc R U . . .
C8 C 0.55483(5) 0.8037(3) 0.51380(11) 0.0388(4) Uani 1 1 d . . . . .
C9 C 0.55764(6) 0.9616(3) 0.46990(13) 0.0502(5) Uani 1 1 d . . . . .
H9 H 0.5778 1.0206 0.4828 0.060 Uiso 1 1 calc R U . . .
C10 C 0.53050(6) 1.0309(4) 0.40706(15) 0.0631(7) Uani 1 1 d . . . . .
H10 H 0.5325 1.1363 0.3776 0.076 Uiso 1 1 calc R U . . .
C11 C 0.50072(6) 0.9459(4) 0.38776(15) 0.0646(7) Uani 1 1 d . . . . .
H11 H 0.4826 0.9940 0.3454 0.078 Uiso 1 1 calc R U . . .
C12 C 0.61314(7) 1.0654(4) 0.81839(15) 0.0618(7) Uani 1 1 d . . . . .
H12 H 0.6191 1.1404 0.8641 0.074 Uiso 1 1 calc R U . . .
C13 C 0.62177(7) 0.8714(4) 0.82389(13) 0.0609(6) Uani 1 1 d . . . . .
H13 H 0.6334 0.8154 0.8734 0.073 Uiso 1 1 calc R U . . .
C14 C 0.61329(6) 0.7600(3) 0.75639(13) 0.0519(5) Uani 1 1 d . . . . .
H14 H 0.6190 0.6286 0.7604 0.062 Uiso 1 1 calc R U . . .
C15 C 0.59611(5) 0.8440(3) 0.68176(11) 0.0376(4) Uani 1 1 d . . . . .
C16 C 0.62681(5) 0.5719(3) 0.51690(11) 0.0368(4) Uani 1 1 d . . . . .
C17 C 0.66962(5) 0.4907(3) 0.48646(12) 0.0439(5) Uani 1 1 d . . . . .
C18 C 0.68365(5) 0.1621(3) 0.53273(13) 0.0485(5) Uani 1 1 d . . . . .
H18 H 0.6817 0.0544 0.5611 0.058 Uiso 1 1 calc R U . . .
C19 C 0.70353(6) 0.1556(4) 0.49159(15) 0.0618(7) Uani 1 1 d . . . . .
H19 H 0.7150 0.0421 0.4923 0.074 Uiso 1 1 calc R U . . .
C20 C 0.70633(6) 0.3157(4) 0.44980(15) 0.0640(7) Uani 1 1 d . . . . .
H20 H 0.7201 0.3087 0.4236 0.077 Uiso 1 1 calc R U . . .
C21 C 0.68932(6) 0.4868(4) 0.44550(14) 0.0570(6) Uani 1 1 d . . . . .
H21 H 0.6911 0.5938 0.4165 0.068 Uiso 1 1 calc R U . . .
C22 C 0.64468(5) 0.3913(3) 0.56891(11) 0.0342(4) Uani 1 1 d . . . . .
C23 C 0.70658(9) 0.0961(5) 0.80121(17) 0.0850(10) Uani 1 1 d . . . . .
H23 H 0.7022 -0.0282 0.8147 0.102 Uiso 1 1 calc R U . . .
C24 C 0.68330(7) 0.1923(4) 0.73741(15) 0.0670(7) Uani 1 1 d . . . . .
H24 H 0.6636 0.1307 0.7080 0.080 Uiso 1 1 calc R U . . .
C25 C 0.59605(5) 0.5212(3) 0.44545(12) 0.0466(5) Uani 1 1 d . . . . .
H25A H 0.5873 0.6368 0.4147 0.070 Uiso 1 1 calc R U . . .
H25B H 0.5803 0.4676 0.4627 0.070 Uiso 1 1 calc R U . . .
H25C H 0.6010 0.4267 0.4135 0.070 Uiso 1 1 calc R U . . .
C26 C 0.52455(5) 0.7190(3) 0.49378(14) 0.0515(5) Uani 1 1 d . . . . .
H26 H 0.5224 0.6136 0.5230 0.062 Uiso 1 1 calc R U . . .
C27 C 0.49753(6) 0.7900(4) 0.43066(16) 0.0638(7) Uani 1 1 d . . . . .
H27 H 0.4773 0.7322 0.4174 0.077 Uiso 1 1 calc R U . . .
C28 C 0.58729(5) 1.0392(3) 0.67722(12) 0.0418(4) Uani 1 1 d . . . . .
H28 H 0.5757 1.0966 0.6280 0.050 Uiso 1 1 calc R U . . .
C29 C 0.59573(6) 1.1484(3) 0.74555(14) 0.0567(6) Uani 1 1 d . . . . .
H29 H 0.5896 1.2790 0.7422 0.068 Uiso 1 1 calc R U . . .
C30 C 0.5000 0.5481(9) 0.2500 0.200(5) Uani 1 2 d S T P . .
H30A H 0.5099 0.6319 0.2960 0.240 Uiso 0.5 1 calc R U P . .
H30B H 0.4901 0.6319 0.2040 0.240 Uiso 0.5 1 calc R U P . .


_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 O1 1.4915(14) . ?
P1 C7 1.836(2) . ?
P1 C8 1.802(2) . ?
P1 C15 1.794(2) . ?
O2 C16 1.470(2) . ?
O2 C17 1.371(3) . ?
O3 H3 0.8200 . ?
O3 C22 1.410(2) . ?
Cl1 C30 1.729(3) . ?
C32 C17 1.388(3) . ?
C32 C18 1.378(3) . ?
C32 C22 1.502(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.360(5) . ?
C1 C23 1.357(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.380(3) . ?
C4 C5 1.476(3) . ?
C4 C24 1.381(3) . ?
C5 C6 1.325(3) . ?
C5 C22 1.531(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.507(3) . ?
C7 H7 0.9800 . ?
C7 C16 1.535(3) . ?
C8 C9 1.388(3) . ?
C8 C26 1.384(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(4) . ?
C11 H11 0.9300 . ?
C11 C27 1.372(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(4) . ?
C12 C29 1.373(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(3) . ?
C15 C28 1.387(3) . ?
C16 C22 1.571(3) . ?
C16 C25 1.511(3) . ?
C17 C21 1.381(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(4) . ?
C21 H21 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.382(4) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26 0.9300 . ?
C26 C27 1.384(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.380(3) . ?
C29 H29 0.9300 . ?
C30 Cl1 1.729(3) 2_655 ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?

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
O1 P1 C7 110.83(9) . . ?
O1 P1 C8 112.33(9) . . ?
O1 P1 C15 112.41(9) . . ?
C8 P1 C7 108.19(9) . . ?
C15 P1 C7 104.92(9) . . ?
C15 P1 C8 107.79(9) . . ?
C17 O2 C16 106.93(15) . . ?
C22 O3 H3 109.5 . . ?
C17 C32 C22 107.48(17) . . ?
C18 C32 C17 120.19(19) . . ?
C18 C32 C22 132.32(19) . . ?
C2 C1 H1 120.3 . . ?
C23 C1 H1 120.3 . . ?
C23 C1 C2 119.5(3) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 C24 117.9(2) . . ?
C24 C4 C5 121.4(2) . . ?
C4 C5 C22 122.63(16) . . ?
C6 C5 C4 126.82(18) . . ?
C6 C5 C22 110.55(16) . . ?
C5 C6 H6 123.3 . . ?
C5 C6 C7 113.40(17) . . ?
C7 C6 H6 123.3 . . ?
P1 C7 H7 111.8 . . ?
C6 C7 P1 107.09(14) . . ?
C6 C7 H7 111.8 . . ?
C6 C7 C16 101.91(15) . . ?
C16 C7 P1 112.05(13) . . ?
C16 C7 H7 111.8 . . ?
C9 C8 P1 123.94(16) . . ?
C26 C8 P1 117.04(16) . . ?
C26 C8 C9 119.01(19) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C27 120.2(2) . . ?
C27 C11 H11 119.9 . . ?
C13 C12 H12 119.9 . . ?
C29 C12 H12 119.9 . . ?
C29 C12 C13 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 P1 118.12(15) . . ?
C28 C15 P1 122.76(15) . . ?
C28 C15 C14 119.01(19) . . ?
O2 C16 C7 106.26(15) . . ?
O2 C16 C22 103.32(15) . . ?
O2 C16 C25 107.39(16) . . ?
C7 C16 C22 105.08(15) . . ?
C25 C16 C7 119.21(17) . . ?
C25 C16 C22 114.20(16) . . ?
O2 C17 C32 113.15(18) . . ?
O2 C17 C21 124.6(2) . . ?
C21 C17 C32 122.2(2) . . ?
C32 C18 H18 120.8 . . ?
C32 C18 C19 118.3(2) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.5(2) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 118.9 . . ?
C19 C20 C21 122.1(2) . . ?
C21 C20 H20 118.9 . . ?
C17 C21 C20 116.6(2) . . ?
C17 C21 H21 121.7 . . ?
C20 C21 H21 121.7 . . ?
O3 C22 C32 112.49(15) . . ?
O3 C22 C5 113.50(15) . . ?
O3 C22 C16 114.60(15) . . ?
C32 C22 C5 111.67(15) . . ?
C32 C22 C16 101.27(15) . . ?
C5 C22 C16 102.28(14) . . ?
C1 C23 H23 119.7 . . ?
C1 C23 C24 120.5(3) . . ?
C24 C23 H23 119.7 . . ?
C4 C24 C23 121.2(3) . . ?
C4 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C16 C25 H25A 109.5 . . ?
C16 C25 H25B 109.5 . . ?
C16 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C8 C26 H26 119.7 . . ?
C27 C26 C8 120.5(2) . . ?
C27 C26 H26 119.7 . . ?
C11 C27 C26 119.8(2) . . ?
C11 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C15 C28 H28 119.9 . . ?
C29 C28 C15 120.1(2) . . ?
C29 C28 H28 119.9 . . ?
C12 C29 C28 120.3(2) . . ?
C12 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
Cl1 C30 Cl1 115.8(4) 2_655 . ?
Cl1 C30 H30A 108.3 2_655 . ?
Cl1 C30 H30A 108.3 . . ?
Cl1 C30 H30B 108.3 2_655 . ?
Cl1 C30 H30B 108.3 . . ?
H30A C30 H30B 107.4 . . ?

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
P1 C7 C16 O2 162.24(12) . . . . ?
P1 C7 C16 C22 -88.66(15) . . . . ?
P1 C7 C16 C25 40.9(2) . . . . ?
P1 C8 C9 C10 178.62(19) . . . . ?
P1 C8 C26 C27 -178.7(2) . . . . ?
P1 C15 C28 C29 -175.46(18) . . . . ?
O1 P1 C7 C6 -66.10(14) . . . . ?
O1 P1 C7 C16 44.84(16) . . . . ?
O1 P1 C8 C9 -154.23(18) . . . . ?
O1 P1 C8 C26 24.8(2) . . . . ?
O1 P1 C15 C14 34.9(2) . . . . ?
O1 P1 C15 C28 -148.85(17) . . . . ?
O2 C16 C22 O3 -148.08(15) . . . . ?
O2 C16 C22 C32 -26.73(17) . . . . ?
O2 C16 C22 C5 88.66(16) . . . . ?
O2 C17 C21 C20 -178.5(2) . . . . ?
C32 C17 C21 C20 0.4(3) . . . . ?
C32 C18 C19 C20 0.1(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C23 C24 C4 -1.1(5) . . . . ?
C2 C1 C23 C24 1.0(5) . . . . ?
C2 C3 C4 C5 178.6(2) . . . . ?
C2 C3 C4 C24 0.6(4) . . . . ?
C3 C4 C5 C6 -45.6(3) . . . . ?
C3 C4 C5 C22 134.0(2) . . . . ?
C3 C4 C24 C23 0.3(4) . . . . ?
C4 C5 C6 C7 -174.20(19) . . . . ?
C4 C5 C22 O3 67.0(2) . . . . ?
C4 C5 C22 C32 -61.4(2) . . . . ?
C4 C5 C22 C16 -169.00(17) . . . . ?
C5 C4 C24 C23 -177.7(3) . . . . ?
C5 C6 C7 P1 97.29(18) . . . . ?
C5 C6 C7 C16 -20.5(2) . . . . ?
C6 C5 C22 O3 -113.31(19) . . . . ?
C6 C5 C22 C32 118.25(19) . . . . ?
C6 C5 C22 C16 10.7(2) . . . . ?
C6 C7 C16 O2 -83.58(17) . . . . ?
C6 C7 C16 C22 25.52(19) . . . . ?
C6 C7 C16 C25 155.09(18) . . . . ?
C7 P1 C8 C9 -31.6(2) . . . . ?
C7 P1 C8 C26 147.45(17) . . . . ?
C7 P1 C15 C14 -85.59(18) . . . . ?
C7 P1 C15 C28 90.62(18) . . . . ?
C7 C16 C22 O3 100.71(17) . . . . ?
C7 C16 C22 C32 -137.95(15) . . . . ?
C7 C16 C22 C5 -22.56(18) . . . . ?
C8 P1 C7 C6 170.33(12) . . . . ?
C8 P1 C7 C16 -78.73(15) . . . . ?
C8 P1 C15 C14 159.27(17) . . . . ?
C8 P1 C15 C28 -24.5(2) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C8 C26 C27 C11 -0.2(4) . . . . ?
C9 C8 C26 C27 0.3(3) . . . . ?
C9 C10 C11 C27 -0.2(4) . . . . ?
C10 C11 C27 C26 0.1(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C12 C29 C28 -1.2(4) . . . . ?
C13 C14 C15 P1 175.1(2) . . . . ?
C13 C14 C15 C28 -1.3(3) . . . . ?
C14 C15 C28 C29 0.7(3) . . . . ?
C15 P1 C7 C6 55.47(14) . . . . ?
C15 P1 C7 C16 166.42(13) . . . . ?
C15 P1 C8 C9 81.4(2) . . . . ?
C15 P1 C8 C26 -99.59(18) . . . . ?
C15 C28 C29 C12 0.5(4) . . . . ?
C16 O2 C17 C32 -15.3(2) . . . . ?
C16 O2 C17 C21 163.6(2) . . . . ?
C17 O2 C16 C7 136.45(16) . . . . ?
C17 O2 C16 C22 26.11(19) . . . . ?
C17 O2 C16 C25 -94.93(18) . . . . ?
C17 C32 C18 C19 1.2(3) . . . . ?
C17 C32 C22 O3 141.52(16) . . . . ?
C17 C32 C22 C5 -89.50(19) . . . . ?
C17 C32 C22 C16 18.71(19) . . . . ?
C18 C32 C17 O2 177.47(18) . . . . ?
C18 C32 C17 C21 -1.5(3) . . . . ?
C18 C32 C22 O3 -39.3(3) . . . . ?
C18 C32 C22 C5 89.7(3) . . . . ?
C18 C32 C22 C16 -162.1(2) . . . . ?
C18 C19 C20 C21 -1.2(4) . . . . ?
C19 C20 C21 C17 1.0(4) . . . . ?
C22 C32 C17 O2 -3.2(2) . . . . ?
C22 C32 C17 C21 177.8(2) . . . . ?
C22 C32 C18 C19 -177.9(2) . . . . ?
C22 C5 C6 C7 6.1(2) . . . . ?
C23 C1 C2 C3 -0.2(5) . . . . ?
C24 C4 C5 C6 132.3(2) . . . . ?
C24 C4 C5 C22 -48.0(3) . . . . ?
C25 C16 C22 O3 -31.8(2) . . . . ?
C25 C16 C22 C32 89.58(19) . . . . ?
C25 C16 C22 C5 -155.04(17) . . . . ?
C26 C8 C9 C10 -0.4(3) . . . . ?
C29 C12 C13 C14 0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_wtl_hhl_deine_syn_0ma_a
_audit_block_doi                 10.5517/ccdc.csd.cc2bwxlr
_database_code_depnum_ccdc_archive 'CCDC 2171785'
loop_
_audit_author_name
_audit_author_address
'Hui-Lin Hu'
;Sichuan University
China
;
_audit_update_record             
;
2022-05-10 deposited with the CCDC.	2023-08-03 downloaded from the CCDC.
;
_audit_creation_date             2021-09-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H25 O3 P'
_chemical_formula_sum            'C30 H25 O3 P'
_chemical_formula_weight         464.47
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.560(2)
_cell_length_b                   10.831(2)
_cell_length_c                   11.869(2)
_cell_angle_alpha                68.716(6)
_cell_angle_beta                 78.861(6)
_cell_angle_gamma                85.017(6)
_cell_volume                     1240.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    252(2)
_cell_measurement_theta_max      26.707
_cell_measurement_theta_min      2.213
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1538 before and 0.0937 after correction.
The Ratio of minimum to maximum transmission is 0.7090.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41898
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.620
_diffrn_reflns_theta_min         1.870
_diffrn_ambient_temperature      252.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4205
_reflns_number_total             5754
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5754
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.3577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1331
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C30(H30), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21),
  C22(H22), C23(H23), C24(H24), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
P1 P 0.66535(4) 0.54356(5) 0.14434(4) 0.04481(14) Uani 1 1 d . . . . .
O1 O 0.67708(13) 0.50159(15) 0.03720(12) 0.0638(4) Uani 1 1 d . . . . .
O2 O 0.45900(16) 0.14533(13) 0.25844(13) 0.0693(4) Uani 1 1 d . . . . .
O3 O 0.41401(18) 0.33813(14) 0.50082(13) 0.0791(5) Uani 1 1 d . . . . .
C30 C 0.51894(16) 0.48788(16) 0.25682(14) 0.0409(4) Uani 1 1 d . . . . .
H30 H 0.5253 0.5121 0.3283 0.049 Uiso 1 1 calc R U . . .
C29 C 0.40145(16) 0.55768(16) 0.20709(15) 0.0426(4) Uani 1 1 d . . . . .
H29 H 0.3885 0.5568 0.1312 0.051 Uiso 1 1 calc R U . . .
C28 C 0.19946(17) 0.69105(17) 0.22353(17) 0.0491(4) Uani 1 1 d . . . . .
C1 C 0.2679(2) -0.0934(2) 0.5168(3) 0.0774(7) Uani 1 1 d . . . . .
H1 H 0.2353 -0.1784 0.5378 0.093 Uiso 1 1 calc R U . . .
C2 C 0.2414(3) -0.0305(2) 0.6004(3) 0.0842(7) Uani 1 1 d . . . . .
H2 H 0.1903 -0.0717 0.6777 0.101 Uiso 1 1 calc R U . . .
C3 C 0.2900(2) 0.0930(2) 0.5705(2) 0.0731(6) Uani 1 1 d . . . . .
H3 H 0.2732 0.1358 0.6281 0.088 Uiso 1 1 calc R U . . .
C4 C 0.36382(18) 0.15566(18) 0.45546(17) 0.0525(4) Uani 1 1 d . . . . .
C5 C 0.42535(18) 0.28255(17) 0.42730(16) 0.0494(4) Uani 1 1 d . . . . .
C6 C 0.50998(17) 0.33606(16) 0.30229(15) 0.0440(4) Uani 1 1 d . . . . .
H6 H 0.5980 0.2987 0.3110 0.053 Uiso 1 1 calc R U . . .
C7 C 0.31561(17) 0.62009(17) 0.26469(16) 0.0473(4) Uani 1 1 d . . . . .
H7 H 0.3308 0.6188 0.3406 0.057 Uiso 1 1 calc R U . . .
C8 C 0.1548(2) 0.6874(2) 0.1220(2) 0.0658(5) Uani 1 1 d . . . . .
H8 H 0.1991 0.6357 0.0777 0.079 Uiso 1 1 calc R U . . .
C9 C 0.0464(2) 0.7589(3) 0.0862(3) 0.0841(7) Uani 1 1 d . . . . .
H9 H 0.0172 0.7552 0.0175 0.101 Uiso 1 1 calc R U . . .
C10 C -0.0193(2) 0.8348(3) 0.1482(3) 0.0897(8) Uani 1 1 d . . . . .
H10 H -0.0929 0.8838 0.1222 0.108 Uiso 1 1 calc R U . . .
C11 C 0.13002(19) 0.7673(2) 0.2868(2) 0.0618(5) Uani 1 1 d . . . . .
H11 H 0.1566 0.7702 0.3569 0.074 Uiso 1 1 calc R U . . .
C12 C 0.0219(2) 0.8393(2) 0.2480(3) 0.0827(8) Uani 1 1 d . . . . .
H12 H -0.0234 0.8918 0.2911 0.099 Uiso 1 1 calc R U . . .
C13 C 0.66522(17) 0.72041(18) 0.10008(15) 0.0487(4) Uani 1 1 d . . . . .
C14 C 0.6192(2) 0.78759(19) 0.1783(2) 0.0613(5) Uani 1 1 d . . . . .
H14 H 0.5863 0.7405 0.2613 0.074 Uiso 1 1 calc R U . . .
C15 C 0.6212(2) 0.9248(2) 0.1353(3) 0.0813(7) Uani 1 1 d . . . . .
H15 H 0.5889 0.9705 0.1890 0.098 Uiso 1 1 calc R U . . .
C16 C 0.6695(3) 0.9932(3) 0.0161(3) 0.0991(10) Uani 1 1 d . . . . .
H16 H 0.6715 1.0862 -0.0124 0.119 Uiso 1 1 calc R U . . .
C17 C 0.7145(3) 0.9285(3) -0.0618(3) 0.1036(11) Uani 1 1 d . . . . .
H17 H 0.7472 0.9768 -0.1445 0.124 Uiso 1 1 calc R U . . .
C18 C 0.7130(2) 0.7927(3) -0.02144(19) 0.0744(7) Uani 1 1 d . . . . .
H18 H 0.7447 0.7485 -0.0766 0.089 Uiso 1 1 calc R U . . .
C19 C 0.79629(17) 0.47824(18) 0.22829(17) 0.0485(4) Uani 1 1 d . . . . .
C20 C 0.8068(2) 0.5024(2) 0.33269(19) 0.0601(5) Uani 1 1 d . . . . .
H20 H 0.7432 0.5543 0.3630 0.072 Uiso 1 1 calc R U . . .
C21 C 0.9087(3) 0.4517(3) 0.3924(2) 0.0776(7) Uani 1 1 d . . . . .
H21 H 0.9144 0.4686 0.4635 0.093 Uiso 1 1 calc R U . . .
C22 C 1.0013(3) 0.3774(3) 0.3498(3) 0.0960(9) Uani 1 1 d . . . . .
H22 H 1.0717 0.3438 0.3906 0.115 Uiso 1 1 calc R U . . .
C23 C 0.9926(3) 0.3513(3) 0.2481(3) 0.1092(10) Uani 1 1 d . . . . .
H23 H 1.0564 0.2984 0.2194 0.131 Uiso 1 1 calc R U . . .
C24 C 0.8903(2) 0.4019(3) 0.1864(2) 0.0839(8) Uani 1 1 d . . . . .
H24 H 0.8852 0.3840 0.1157 0.101 Uiso 1 1 calc R U . . .
C25 C 0.4627(2) 0.28722(18) 0.21350(18) 0.0647(6) Uani 1 1 d . . . . .
H25A H 0.3760 0.3239 0.2017 0.078 Uiso 1 1 calc R U . . .
H25B H 0.5201 0.3185 0.1337 0.078 Uiso 1 1 calc R U . . .
C26 C 0.3879(2) 0.09078(18) 0.37210(19) 0.0550(5) Uani 1 1 d . . . . .
C27 C 0.3405(2) -0.0352(2) 0.4036(2) 0.0703(6) Uani 1 1 d . . . . .
H27 H 0.3582 -0.0799 0.3475 0.084 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 O1 1.4793(12) . ?
P1 C30 1.8210(17) . ?
P1 C13 1.793(2) . ?
P1 C19 1.8043(19) . ?
O2 C25 1.434(2) . ?
O2 C26 1.356(2) . ?
O3 C5 1.211(2) . ?
C30 H30 0.9900 . ?
C30 C29 1.502(2) . ?
C30 C6 1.539(2) . ?
C29 H29 0.9400 . ?
C29 C7 1.317(2) . ?
C28 C7 1.459(2) . ?
C28 C8 1.390(3) . ?
C28 C11 1.384(3) . ?
C1 H1 0.9400 . ?
C1 C2 1.371(3) . ?
C1 C27 1.364(3) . ?
C2 H2 0.9400 . ?
C2 C3 1.373(3) . ?
C3 H3 0.9400 . ?
C3 C4 1.393(3) . ?
C4 C5 1.470(3) . ?
C4 C26 1.383(3) . ?
C5 C6 1.513(2) . ?
C6 H6 0.9900 . ?
C6 C25 1.515(2) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C8 C9 1.373(3) . ?
C9 H9 0.9400 . ?
C9 C10 1.357(4) . ?
C10 H10 0.9400 . ?
C10 C12 1.356(4) . ?
C11 H11 0.9400 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.372(3) . ?
C13 C18 1.384(3) . ?
C14 H14 0.9400 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9400 . ?
C15 C16 1.355(4) . ?
C16 H16 0.9400 . ?
C16 C17 1.347(4) . ?
C17 H17 0.9400 . ?
C17 C18 1.372(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.382(3) . ?
C19 C24 1.371(3) . ?
C20 H20 0.9400 . ?
C20 C21 1.368(3) . ?
C21 H21 0.9400 . ?
C21 C22 1.351(4) . ?
C22 H22 0.9400 . ?
C22 C23 1.357(4) . ?
C23 H23 0.9400 . ?
C23 C24 1.384(4) . ?
C24 H24 0.9400 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 C27 1.388(3) . ?
C27 H27 0.9400 . ?

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
O1 P1 C30 113.89(8) . . ?
O1 P1 C13 111.96(9) . . ?
O1 P1 C19 111.77(8) . . ?
C13 P1 C30 106.22(8) . . ?
C13 P1 C19 107.32(8) . . ?
C19 P1 C30 105.18(8) . . ?
C26 O2 C25 114.44(15) . . ?
P1 C30 H30 107.4 . . ?
C29 C30 P1 111.22(11) . . ?
C29 C30 H30 107.4 . . ?
C29 C30 C6 112.69(14) . . ?
C6 C30 P1 110.55(11) . . ?
C6 C30 H30 107.4 . . ?
C30 C29 H29 118.4 . . ?
C7 C29 C30 123.16(16) . . ?
C7 C29 H29 118.4 . . ?
C8 C28 C7 123.20(17) . . ?
C11 C28 C7 119.18(18) . . ?
C11 C28 C8 117.62(19) . . ?
C2 C1 H1 119.3 . . ?
C27 C1 H1 119.3 . . ?
C27 C1 C2 121.4(2) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.59(18) . . ?
C26 C4 C3 118.78(18) . . ?
C26 C4 C5 120.37(17) . . ?
O3 C5 C4 122.53(17) . . ?
O3 C5 C6 121.88(16) . . ?
C4 C5 C6 115.52(15) . . ?
C30 C6 H6 107.5 . . ?
C5 C6 C30 111.45(13) . . ?
C5 C6 H6 107.5 . . ?
C5 C6 C25 109.60(16) . . ?
C25 C6 C30 113.16(14) . . ?
C25 C6 H6 107.5 . . ?
C29 C7 C28 127.09(17) . . ?
C29 C7 H7 116.5 . . ?
C28 C7 H7 116.5 . . ?
C28 C8 H8 119.8 . . ?
C9 C8 C28 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.2 . . ?
C12 C10 C9 119.5(2) . . ?
C12 C10 H10 120.2 . . ?
C28 C11 H11 119.7 . . ?
C12 C11 C28 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C12 C11 120.6(2) . . ?
C10 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 P1 124.16(14) . . ?
C14 C13 C18 118.5(2) . . ?
C18 C13 P1 117.30(17) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.3(3) . . ?
C17 C18 H18 119.8 . . ?
C20 C19 P1 122.94(14) . . ?
C24 C19 P1 118.71(16) . . ?
C24 C19 C20 118.34(19) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 120.1(2) . . ?
C19 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
O2 C25 C6 111.06(15) . . ?
O2 C25 H25A 109.4 . . ?
O2 C25 H25B 109.4 . . ?
C6 C25 H25A 109.4 . . ?
C6 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
O2 C26 C4 122.20(17) . . ?
O2 C26 C27 117.47(18) . . ?
C4 C26 C27 120.3(2) . . ?
C1 C27 C26 119.4(2) . . ?
C1 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?

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
P1 C30 C29 C7 -127.06(16) . . . . ?
P1 C30 C6 C5 156.59(12) . . . . ?
P1 C30 C6 C25 -79.35(17) . . . . ?
P1 C13 C14 C15 -178.94(17) . . . . ?
P1 C13 C18 C17 179.31(19) . . . . ?
P1 C19 C20 C21 -179.34(17) . . . . ?
P1 C19 C24 C23 179.5(2) . . . . ?
O1 P1 C30 C29 -69.12(13) . . . . ?
O1 P1 C30 C6 56.86(14) . . . . ?
O1 P1 C13 C14 160.29(16) . . . . ?
O1 P1 C13 C18 -18.71(18) . . . . ?
O1 P1 C19 C20 -179.51(16) . . . . ?
O1 P1 C19 C24 1.0(2) . . . . ?
O2 C26 C27 C1 -179.6(2) . . . . ?
O3 C5 C6 C30 -29.1(3) . . . . ?
O3 C5 C6 C25 -155.15(19) . . . . ?
C30 P1 C13 C14 35.40(19) . . . . ?
C30 P1 C13 C18 -143.60(16) . . . . ?
C30 P1 C19 C20 -55.44(18) . . . . ?
C30 P1 C19 C24 125.04(19) . . . . ?
C30 C29 C7 C28 179.60(16) . . . . ?
C30 C6 C25 O2 178.58(16) . . . . ?
C29 C30 C6 C5 -78.27(18) . . . . ?
C29 C30 C6 C25 45.8(2) . . . . ?
C28 C8 C9 C10 0.2(4) . . . . ?
C28 C11 C12 C10 1.1(4) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C1 C27 C26 -0.4(4) . . . . ?
C2 C3 C4 C5 -174.6(2) . . . . ?
C2 C3 C4 C26 -0.3(3) . . . . ?
C3 C4 C5 O3 -0.7(3) . . . . ?
C3 C4 C5 C6 176.20(18) . . . . ?
C3 C4 C26 O2 -179.97(19) . . . . ?
C3 C4 C26 C27 -0.8(3) . . . . ?
C4 C5 C6 C30 153.98(15) . . . . ?
C4 C5 C6 C25 27.9(2) . . . . ?
C4 C26 C27 C1 1.2(3) . . . . ?
C5 C4 C26 O2 -5.7(3) . . . . ?
C5 C4 C26 C27 173.41(19) . . . . ?
C5 C6 C25 O2 -56.4(2) . . . . ?
C6 C30 C29 C7 108.15(18) . . . . ?
C7 C28 C8 C9 -178.5(2) . . . . ?
C7 C28 C11 C12 177.88(19) . . . . ?
C8 C28 C7 C29 8.7(3) . . . . ?
C8 C28 C11 C12 -1.4(3) . . . . ?
C8 C9 C10 C12 -0.6(4) . . . . ?
C9 C10 C12 C11 0.0(4) . . . . ?
C11 C28 C7 C29 -170.59(18) . . . . ?
C11 C28 C8 C9 0.8(3) . . . . ?
C13 P1 C30 C29 54.57(13) . . . . ?
C13 P1 C30 C6 -179.44(11) . . . . ?
C13 P1 C19 C20 57.37(18) . . . . ?
C13 P1 C19 C24 -122.14(19) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C19 P1 C30 C29 168.17(11) . . . . ?
C19 P1 C30 C6 -65.85(13) . . . . ?
C19 P1 C13 C14 -76.71(18) . . . . ?
C19 P1 C13 C18 104.29(17) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C19 C24 C23 -0.1(4) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C21 C22 C23 C24 1.0(5) . . . . ?
C22 C23 C24 C19 -0.5(5) . . . . ?
C24 C19 C20 C21 0.2(3) . . . . ?
C25 O2 C26 C4 -23.8(3) . . . . ?
C25 O2 C26 C27 156.99(19) . . . . ?
C26 O2 C25 C6 55.5(2) . . . . ?
C26 C4 C5 O3 -174.8(2) . . . . ?
C26 C4 C5 C6 2.1(3) . . . . ?
C27 C1 C2 C3 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_wtl004
_audit_block_doi                 10.5517/ccdc.csd.cc2d3d86
_database_code_depnum_ccdc_archive 'CCDC 2207797'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2022-09-16 deposited with the CCDC.	2023-08-03 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         'C30 H25 O3 P'
_chemical_formula_sum            'C30 H25 O3 P'
_chemical_formula_weight         464.47

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2171(2)
_cell_length_b                   17.9048(6)
_cell_length_c                   14.5888(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.2740(10)
_cell_angle_gamma                90
_cell_volume                     2376.12(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5930
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8111
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            17751
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5409
_reflns_number_gt                4156
_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 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)+(0.0601P)²+2.0486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5409
_refine_ls_number_parameters     321
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1381
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_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
P P 0.24007(6) 0.51192(3) 0.30169(4) 0.02647(16) Uani 1 1 d . . . . .
O1 O 0.5223(2) 0.53639(10) 0.17808(16) 0.0562(6) Uani 1 1 d D . . . .
H1O H 0.61(2) 0.55(3) 0.18(4) 1.5(5) Uiso 1 1 d D . . . .
O2 O 0.83098(19) 0.48051(13) 0.20447(13) 0.0482(5) Uani 1 1 d D . . . .
H2O H 0.921(2) 0.497(2) 0.211(3) 0.093(13) Uiso 1 1 d D . . . .
O3 O 0.11224(16) 0.50998(10) 0.22440(12) 0.0357(4) Uani 1 1 d . . . . .
C1X C 0.3493(6) 0.4538(4) 0.1004(3) 0.0234(10) Uani 0.624(10) 1 d D . P A 1
H1XA H 0.278549 0.495017 0.094413 0.035 Uiso 0.624(10) 1 calc R U P A 1
H1XB H 0.296995 0.406253 0.102038 0.035 Uiso 0.624(10) 1 calc R U P A 1
H1XC H 0.401998 0.454066 0.047131 0.035 Uiso 0.624(10) 1 calc R U P A 1
C1Y C 0.3324(10) 0.4272(6) 0.1136(6) 0.0234(10) Uani 0.376(10) 1 d D . P A 2
H1YA H 0.242557 0.457076 0.109455 0.035 Uiso 0.376(10) 1 calc R U P A 2
H1YB H 0.312634 0.376107 0.132370 0.035 Uiso 0.376(10) 1 calc R U P A 2
H1YC H 0.365077 0.426188 0.052939 0.035 Uiso 0.376(10) 1 calc R U P A 2
C2 C 0.4562(3) 0.46278(13) 0.18767(16) 0.0318(5) Uani 1 1 d D . . . .
C3 C 0.3898(2) 0.45678(12) 0.27681(15) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.4555(2) 0.40097(12) 0.32808(15) 0.0259(4) Uani 1 1 d . . . . .
H4 H 0.432114 0.386143 0.386487 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5698(2) 0.36506(12) 0.28225(15) 0.0249(4) Uani 1 1 d . . . . .
C6 C 0.5736(2) 0.40119(12) 0.20174(15) 0.0263(4) Uani 1 1 d . . . . .
C11 C 0.6680(2) 0.38983(13) 0.12975(15) 0.0287(5) Uani 1 1 d . . . . .
C12 C 0.7959(2) 0.43229(14) 0.13232(15) 0.0327(5) Uani 1 1 d . . . . .
C13 C 0.8820(3) 0.42487(16) 0.06288(17) 0.0407(6) Uani 1 1 d . . . . .
H13 H 0.969282 0.453539 0.065172 0.049 Uiso 1 1 calc R U . . .
C14 C 0.8403(3) 0.37567(16) -0.00941(18) 0.0458(7) Uani 1 1 d . . . . .
H14 H 0.897600 0.371655 -0.057768 0.055 Uiso 1 1 calc R U . . .
C15 C 0.7166(3) 0.33251(16) -0.01203(19) 0.0487(7) Uani 1 1 d . . . . .
H15 H 0.689939 0.297773 -0.061076 0.058 Uiso 1 1 calc R U . . .
C16 C 0.6306(3) 0.33985(14) 0.05738(18) 0.0401(6) Uani 1 1 d . . . . .
H16 H 0.544767 0.310100 0.055165 0.048 Uiso 1 1 calc R U . . .
C21 C 0.6556(2) 0.30023(13) 0.32200(15) 0.0292(5) Uani 1 1 d . . . . .
C22 C 0.7861(4) 0.2785(2) 0.2929(2) 0.0649(10) Uani 1 1 d . . . . .
H22 H 0.824171 0.307534 0.247741 0.078 Uiso 1 1 calc R U . . .
C23 C 0.8608(4) 0.2154(2) 0.3287(2) 0.0759(12) Uani 1 1 d . . . . .
H23 H 0.948564 0.201032 0.307120 0.091 Uiso 1 1 calc R U . . .
C24 C 0.8095(3) 0.17344(16) 0.39508(19) 0.0514(8) Uani 1 1 d . . . . .
H24 H 0.858481 0.128795 0.417535 0.062 Uiso 1 1 calc R U . . .
C25 C 0.6881(3) 0.19637(18) 0.4283(2) 0.0589(9) Uani 1 1 d . . . . .
H25 H 0.654644 0.169196 0.476768 0.071 Uiso 1 1 calc R U . . .
C26 C 0.6124(3) 0.25916(17) 0.3920(2) 0.0554(8) Uani 1 1 d . . . . .
H26 H 0.527494 0.274286 0.416423 0.067 Uiso 1 1 calc R U . . .
C31 C 0.3052(2) 0.60587(13) 0.32273(16) 0.0301(5) Uani 1 1 d . . . . .
C32 C 0.2122(3) 0.66432(14) 0.28846(18) 0.0401(6) Uani 1 1 d . . . . .
H32 H 0.116448 0.654010 0.255984 0.048 Uiso 1 1 calc R U . . .
C33 C 0.2597(4) 0.73759(16) 0.3019(2) 0.0534(8) Uani 1 1 d . . . . .
H33 H 0.195830 0.777437 0.279236 0.064 Uiso 1 1 calc R U . . .
C34 C 0.3987(4) 0.75287(16) 0.3477(2) 0.0539(8) Uani 1 1 d . . . . .
H34 H 0.430704 0.803195 0.356071 0.065 Uiso 1 1 calc R U . . .
C35 C 0.4921(3) 0.69538(17) 0.3817(2) 0.0489(7) Uani 1 1 d . . . . .
H35 H 0.588106 0.706240 0.413415 0.059 Uiso 1 1 calc R U . . .
C36 C 0.4458(3) 0.62192(14) 0.36964(18) 0.0377(6) Uani 1 1 d . . . . .
H36 H 0.509901 0.582436 0.393339 0.045 Uiso 1 1 calc R U . . .
C41 C 0.1971(3) 0.47473(14) 0.40884(17) 0.0335(5) Uani 1 1 d . . . . .
C42 C 0.1244(3) 0.40662(16) 0.4048(2) 0.0489(7) Uani 1 1 d . . . . .
H42 H 0.099418 0.381440 0.347045 0.059 Uiso 1 1 calc R U . . .
C43 C 0.0882(4) 0.37527(18) 0.4856(3) 0.0625(9) Uani 1 1 d . . . . .
H43 H 0.038709 0.328613 0.483300 0.075 Uiso 1 1 calc R U . . .
C44 C 0.1250(4) 0.4127(2) 0.5691(2) 0.0639(10) Uani 1 1 d . . . . .
H44 H 0.101410 0.391079 0.624357 0.077 Uiso 1 1 calc R U . . .
C45 C 0.1949(3) 0.4803(2) 0.5732(2) 0.0563(8) Uani 1 1 d . . . . .
H45 H 0.218380 0.505716 0.630892 0.068 Uiso 1 1 calc R U . . .
C46 C 0.2311(3) 0.51157(17) 0.49333(18) 0.0420(6) Uani 1 1 d . . . . .
H46 H 0.279619 0.558538 0.496215 0.050 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
P O3 1.4943(16) . ?
P C3 1.781(2) . ?
P C31 1.796(2) . ?
P C41 1.801(2) . ?
O1 C2 1.468(3) . ?
O2 C12 1.359(3) . ?
C1X C2 1.488(5) . ?
C1Y C2 1.574(9) . ?
C2 C3 1.528(3) . ?
C2 C6 1.535(3) . ?
C3 C4 1.334(3) . ?
C4 C5 1.482(3) . ?
C5 C6 1.346(3) . ?
C5 C21 1.470(3) . ?
C6 C11 1.482(3) . ?
C11 C16 1.385(3) . ?
C11 C12 1.398(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.380(4) . ?
C14 C15 1.373(4) . ?
C15 C16 1.389(4) . ?
C21 C26 1.368(3) . ?
C21 C22 1.394(4) . ?
C22 C23 1.381(4) . ?
C23 C24 1.369(4) . ?
C24 C25 1.353(4) . ?
C25 C26 1.383(4) . ?
C31 C32 1.394(3) . ?
C31 C36 1.394(3) . ?
C32 C33 1.387(4) . ?
C33 C34 1.373(4) . ?
C34 C35 1.382(4) . ?
C35 C36 1.385(4) . ?
C41 C42 1.388(4) . ?
C41 C46 1.389(4) . ?
C42 C43 1.394(4) . ?
C43 C44 1.384(5) . ?
C44 C45 1.369(5) . ?
C45 C46 1.382(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
O3 P C3 112.08(10) . . ?
O3 P C31 110.61(10) . . ?
C3 P C31 107.78(10) . . ?
O3 P C41 112.92(11) . . ?
C3 P C41 104.94(10) . . ?
C31 P C41 108.20(11) . . ?
O1 C2 C1X 104.1(3) . . ?
O1 C2 C3 111.93(19) . . ?
C1X C2 C3 114.8(3) . . ?
O1 C2 C6 111.30(19) . . ?
C1X C2 C6 113.1(3) . . ?
C3 C2 C6 101.90(17) . . ?
O1 C2 C1Y 124.3(4) . . ?
C3 C2 C1Y 102.1(4) . . ?
C6 C2 C1Y 102.6(4) . . ?
C4 C3 C2 108.78(18) . . ?
C4 C3 P 126.72(17) . . ?
C2 C3 P 124.36(16) . . ?
C3 C4 C5 111.33(19) . . ?
C6 C5 C21 129.47(19) . . ?
C6 C5 C4 107.78(18) . . ?
C21 C5 C4 122.73(19) . . ?
C5 C6 C11 130.8(2) . . ?
C5 C6 C2 110.17(18) . . ?
C11 C6 C2 119.05(18) . . ?
C16 C11 C12 118.5(2) . . ?
C16 C11 C6 121.8(2) . . ?
C12 C11 C6 119.7(2) . . ?
O2 C12 C13 122.2(2) . . ?
O2 C12 C11 117.4(2) . . ?
C13 C12 C11 120.4(2) . . ?
C14 C13 C12 119.7(2) . . ?
C15 C14 C13 120.6(2) . . ?
C14 C15 C16 119.7(3) . . ?
C11 C16 C15 121.1(3) . . ?
C26 C21 C22 116.5(2) . . ?
C26 C21 C5 121.1(2) . . ?
C22 C21 C5 122.4(2) . . ?
C23 C22 C21 121.0(3) . . ?
C24 C23 C22 120.6(3) . . ?
C25 C24 C23 119.1(3) . . ?
C24 C25 C26 120.3(3) . . ?
C21 C26 C25 122.2(2) . . ?
C32 C31 C36 119.4(2) . . ?
C32 C31 P 118.20(18) . . ?
C36 C31 P 122.39(18) . . ?
C33 C32 C31 119.8(3) . . ?
C34 C33 C32 120.4(3) . . ?
C33 C34 C35 120.3(3) . . ?
C34 C35 C36 120.0(3) . . ?
C35 C36 C31 120.1(2) . . ?
C42 C41 C46 119.6(2) . . ?
C42 C41 P 117.4(2) . . ?
C46 C41 P 123.0(2) . . ?
C41 C42 C43 119.8(3) . . ?
C44 C43 C42 119.5(3) . . ?
C45 C44 C43 120.9(3) . . ?
C44 C45 C46 119.8(3) . . ?
C45 C46 C41 120.4(3) . . ?

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
O1 C2 C3 C4 -120.7(2) . . . . ?
C1X C2 C3 C4 120.9(3) . . . . ?
C6 C2 C3 C4 -1.6(2) . . . . ?
C1Y C2 C3 C4 104.2(4) . . . . ?
O1 C2 C3 P 63.5(2) . . . . ?
C1X C2 C3 P -54.9(4) . . . . ?
C6 C2 C3 P -177.53(15) . . . . ?
C1Y C2 C3 P -71.7(4) . . . . ?
O3 P C3 C4 -123.8(2) . . . . ?
C31 P C3 C4 114.3(2) . . . . ?
C41 P C3 C4 -0.9(2) . . . . ?
O3 P C3 C2 51.4(2) . . . . ?
C31 P C3 C2 -70.6(2) . . . . ?
C41 P C3 C2 174.29(19) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
P C3 C4 C5 176.41(16) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C5 C21 -177.7(2) . . . . ?
C21 C5 C6 C11 -2.9(4) . . . . ?
C4 C5 C6 C11 178.8(2) . . . . ?
C21 C5 C6 C2 176.5(2) . . . . ?
C4 C5 C6 C2 -1.9(2) . . . . ?
O1 C2 C6 C5 121.6(2) . . . . ?
C1X C2 C6 C5 -121.6(3) . . . . ?
C3 C2 C6 C5 2.2(2) . . . . ?
C1Y C2 C6 C5 -103.3(4) . . . . ?
O1 C2 C6 C11 -58.9(3) . . . . ?
C1X C2 C6 C11 57.8(4) . . . . ?
C3 C2 C6 C11 -178.38(19) . . . . ?
C1Y C2 C6 C11 76.1(4) . . . . ?
C5 C6 C11 C16 87.5(3) . . . . ?
C2 C6 C11 C16 -91.8(3) . . . . ?
C5 C6 C11 C12 -94.8(3) . . . . ?
C2 C6 C11 C12 85.9(3) . . . . ?
C16 C11 C12 O2 -179.4(2) . . . . ?
C6 C11 C12 O2 2.8(3) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C6 C11 C12 C13 -177.0(2) . . . . ?
O2 C12 C13 C14 -179.2(2) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C15 -1.8(4) . . . . ?
C13 C14 C15 C16 1.7(4) . . . . ?
C12 C11 C16 C15 -0.9(4) . . . . ?
C6 C11 C16 C15 176.8(2) . . . . ?
C14 C15 C16 C11 -0.4(4) . . . . ?
C6 C5 C21 C26 -163.1(3) . . . . ?
C4 C5 C21 C26 15.1(4) . . . . ?
C6 C5 C21 C22 18.7(4) . . . . ?
C4 C5 C21 C22 -163.1(3) . . . . ?
C26 C21 C22 C23 4.6(5) . . . . ?
C5 C21 C22 C23 -177.1(3) . . . . ?
C21 C22 C23 C24 -1.2(6) . . . . ?
C22 C23 C24 C25 -3.0(6) . . . . ?
C23 C24 C25 C26 3.5(6) . . . . ?
C22 C21 C26 C25 -4.1(5) . . . . ?
C5 C21 C26 C25 177.6(3) . . . . ?
C24 C25 C26 C21 0.1(6) . . . . ?
O3 P C31 C32 18.0(2) . . . . ?
C3 P C31 C32 140.87(19) . . . . ?
C41 P C31 C32 -106.2(2) . . . . ?
O3 P C31 C36 -160.28(19) . . . . ?
C3 P C31 C36 -37.4(2) . . . . ?
C41 P C31 C36 75.5(2) . . . . ?
C36 C31 C32 C33 -0.5(4) . . . . ?
P C31 C32 C33 -178.8(2) . . . . ?
C31 C32 C33 C34 0.8(4) . . . . ?
C32 C33 C34 C35 -0.6(5) . . . . ?
C33 C34 C35 C36 0.0(5) . . . . ?
C34 C35 C36 C31 0.3(4) . . . . ?
C32 C31 C36 C35 -0.1(4) . . . . ?
P C31 C36 C35 178.2(2) . . . . ?
O3 P C41 C42 47.9(2) . . . . ?
C3 P C41 C42 -74.5(2) . . . . ?
C31 P C41 C42 170.68(19) . . . . ?
O3 P C41 C46 -131.0(2) . . . . ?
C3 P C41 C46 106.7(2) . . . . ?
C31 P C41 C46 -8.2(2) . . . . ?
C46 C41 C42 C43 -1.0(4) . . . . ?
P C41 C42 C43 -179.9(2) . . . . ?
C41 C42 C43 C44 0.2(4) . . . . ?
C42 C43 C44 C45 0.7(5) . . . . ?
C43 C44 C45 C46 -0.8(5) . . . . ?
C44 C45 C46 C41 0.0(4) . . . . ?
C42 C41 C46 C45 0.9(4) . . . . ?
P C41 C46 C45 179.8(2) . . . . ?

_refine_diff_density_max         0.612
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
