# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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 
# this file and to allow appropriate attribution of the data. 
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data_220530d
_database_code_depnum_ccdc_archive 'CCDC 2216572'
loop_
_audit_author_name
_audit_author_address
lin
; Liaocheng university
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-05-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H38 Cl O3 P'
_chemical_formula_sum            'C31 H38 Cl O3 P'
_chemical_formula_weight         525.03
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.5468(7)
_cell_length_b                   16.2047(16)
_cell_length_c                   27.749(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2943.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1366
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.471
_cell_measurement_theta_min      2.514
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_unetI/netI     0.1371
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11499
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         1.932
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2227
_reflns_number_total             5177
_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 v6.02A (Bruker, 2001)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.4(2)
_refine_ls_extinction_coef       0.0034(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5177
_refine_ls_number_restraints     918
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0740
_refine_ls_restrained_S_all      0.913
_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)+(0.0944P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1692
_refine_ls_wR_factor_ref         0.2052
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
3.a Ternary CH refined with riding coordinates:
 C16(H16), C20(H20), C24(H24), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C23(H23A,H23B), C29(H29A,H29B), C31(H31A,H31B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C19(H19), C21(H21), C22(H22), C26(H26), C27(H27), C32(H32)
3.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C33(H33A,H33B,H33C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.9924(4) 0.92829(14) 0.14163(7) 0.0571(6) Uani 1 1 d . U . . .
Cl1 Cl 1.0615(5) 0.9787(2) -0.10570(8) 0.1072(11) Uani 1 1 d . U . . .
O35 O 0.8323(8) 0.9195(3) 0.18332(17) 0.0635(13) Uani 1 1 d . U . . .
O2 O 0.5440(8) 0.9561(4) 0.10502(19) 0.0696(16) Uani 1 1 d . U . . .
H2 H 0.4466 0.9495 0.1232 0.104 Uiso 1 1 calc R U . . .
C3 C 0.9947(15) 0.8344(5) 0.1070(3) 0.0691(17) Uani 1 1 d . U . . .
C4 C 0.9234(12) 1.0062(5) 0.0540(3) 0.0570(16) Uani 1 1 d . U . . .
C5 C 1.0120(15) 0.9891(5) -0.0448(3) 0.0632(19) Uani 1 1 d . U . . .
C6 C 1.1185(13) 0.9887(5) 0.0370(3) 0.0628(17) Uani 1 1 d . U . . .
H6 H 1.2241 0.9838 0.0592 0.075 Uiso 1 1 calc R U . . .
C7 C 0.8847(12) 1.0175(5) 0.1078(3) 0.0575(16) Uani 1 1 d . U . . .
C8 C 0.9997(14) 1.0955(5) 0.1268(3) 0.0631(17) Uani 1 1 d . U . . .
H8A H 0.9648 1.1032 0.1605 0.076 Uiso 1 1 calc R U . . .
H8B H 1.1453 1.0849 0.1252 0.076 Uiso 1 1 calc R U . . .
C9 C 1.1632(14) 0.9782(5) -0.0113(3) 0.065(2) Uani 1 1 d . U . . .
H9 H 1.2946 0.9639 -0.0210 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7721(14) 1.0182(6) 0.0192(3) 0.0639(18) Uani 1 1 d . U . . .
H10 H 0.6405 1.0327 0.0285 0.077 Uiso 1 1 calc R U . . .
C11 C 0.6551(13) 1.0278(5) 0.1192(3) 0.0642(18) Uani 1 1 d . U . . .
H11A H 0.6371 1.0371 0.1535 0.077 Uiso 1 1 calc R U . . .
H11B H 0.6023 1.0756 0.1022 0.077 Uiso 1 1 calc R U . . .
C12 C 0.8289(16) 0.8062(6) 0.0805(3) 0.0771(19) Uani 1 1 d . U . . .
H12 H 0.7067 0.8354 0.0809 0.093 Uiso 1 1 calc R U . . .
C13 C 0.7870(15) 1.2235(6) 0.1112(3) 0.078(2) Uani 1 1 d . U . . .
H13 H 0.6962 1.2066 0.1350 0.094 Uiso 1 1 calc R U . . .
C14 C 1.0908(16) 1.2020(6) 0.0661(3) 0.076(2) Uani 1 1 d . U . . .
H14 H 1.2062 1.1708 0.0592 0.092 Uiso 1 1 calc R U . . .
C15 C 0.8180(15) 1.0085(6) -0.0294(3) 0.071(2) Uani 1 1 d . U . . .
H15 H 0.7148 1.0152 -0.0521 0.085 Uiso 1 1 calc R U . . .
C16 C 0.9935(16) 0.9715(7) 0.2773(3) 0.089(2) Uani 1 1 d . U . . .
H16 H 0.9892 1.0058 0.2482 0.106 Uiso 1 1 calc R U . . .
C17 C 0.8457(18) 0.7340(7) 0.0534(4) 0.096(2) Uani 1 1 d . U . . .
H17 H 0.7343 0.7144 0.0361 0.116 Uiso 1 1 calc R U . . .
C18 C 0.9566(14) 1.1748(5) 0.1005(3) 0.0686(18) Uani 1 1 d . U . . .
C19 C 1.0570(17) 1.2772(6) 0.0407(4) 0.093(2) Uani 1 1 d . U . . .
H19 H 1.1470 1.2960 0.0172 0.112 Uiso 1 1 calc R U . . .
C20 C 0.8379(16) 0.9022(6) 0.2702(3) 0.083(2) Uani 1 1 d . U . . .
H20 H 0.7027 0.9282 0.2705 0.099 Uiso 1 1 calc R U . . .
C21 C 1.1752(16) 0.7885(6) 0.1071(4) 0.089(2) Uani 1 1 d . U . . .
H21 H 1.2859 0.8064 0.1253 0.107 Uiso 1 1 calc R U . . .
C22 C 0.7519(18) 1.2964(7) 0.0869(4) 0.093(3) Uani 1 1 d . U . . .
H22 H 0.6382 1.3286 0.0940 0.111 Uiso 1 1 calc R U . . .
C23 C 0.8361(17) 0.8365(7) 0.3108(3) 0.096(2) Uani 1 1 d . U . . .
H23A H 0.9688 0.8101 0.3123 0.115 Uiso 1 1 calc R U . . .
H23B H 0.8121 0.8636 0.3415 0.115 Uiso 1 1 calc R U . . .
C24 C 0.8578(15) 0.8583(6) 0.2222(3) 0.0761(19) Uani 1 1 d . U . . .
H24 H 0.9926 0.8323 0.2198 0.091 Uiso 1 1 calc R U . . .
C25 C 0.690(2) 0.7274(8) 0.2554(4) 0.106(3) Uani 1 1 d . U . . .
H25 H 0.8195 0.6968 0.2542 0.127 Uiso 1 1 calc R U . . .
C26 C 1.1915(19) 0.7165(7) 0.0804(4) 0.102(3) Uani 1 1 d . U . . .
H26 H 1.3110 0.6855 0.0814 0.122 Uiso 1 1 calc R U . . .
C27 C 1.0311(19) 0.6913(7) 0.0526(4) 0.103(3) Uani 1 1 d . U . . .
H27 H 1.0453 0.6451 0.0330 0.124 Uiso 1 1 calc R U . . .
C28 C 1.2168(14) 0.9388(7) 0.2823(3) 0.100(3) Uani 1 1 d . U . . .
H28A H 1.2319 0.9108 0.3126 0.151 Uiso 1 1 calc R U . . .
H28B H 1.3104 0.9843 0.2809 0.151 Uiso 1 1 calc R U . . .
H28C H 1.2456 0.9011 0.2565 0.151 Uiso 1 1 calc R U . . .
C29 C 0.6774(18) 0.7730(7) 0.3031(4) 0.103(3) Uani 1 1 d . U . . .
H29A H 0.5445 0.7992 0.3052 0.124 Uiso 1 1 calc R U . . .
H29B H 0.6863 0.7329 0.3290 0.124 Uiso 1 1 calc R U . . .
C30 C 0.9399(17) 1.0286(8) 0.3207(4) 0.117(4) Uani 1 1 d . U . . .
H30A H 0.8006 1.0465 0.3180 0.176 Uiso 1 1 calc R U . . .
H30B H 1.0285 1.0758 0.3205 0.176 Uiso 1 1 calc R U . . .
H30C H 0.9575 0.9988 0.3502 0.176 Uiso 1 1 calc R U . . .
C31 C 0.6896(15) 0.7932(6) 0.2145(3) 0.087(2) Uani 1 1 d . U . . .
H31A H 0.7105 0.7662 0.1837 0.104 Uiso 1 1 calc R U . . .
H31B H 0.5575 0.8203 0.2136 0.104 Uiso 1 1 calc R U . . .
C32 C 0.8848(19) 1.3202(7) 0.0528(4) 0.093(2) Uani 1 1 d . U . . .
H32 H 0.8579 1.3690 0.0363 0.112 Uiso 1 1 calc R U . . .
C33 C 0.513(2) 0.6671(8) 0.2471(5) 0.160(5) Uani 1 1 d . U . . .
H33A H 0.5163 0.6248 0.2713 0.240 Uiso 1 1 calc R U . . .
H33B H 0.5264 0.6424 0.2158 0.240 Uiso 1 1 calc R U . . .
H33C H 0.3860 0.6964 0.2490 0.240 Uiso 1 1 calc R U . . .
O36 O 1.2048(8) 0.9442(3) 0.15891(17) 0.0624(15) Uani 1 1 d . 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 O35 1.567(5) . ?
P1 C3 1.799(9) . ?
P1 C7 1.862(9) . ?
P1 O36 1.493(5) . ?
Cl1 C5 1.728(8) . ?
O35 C24 1.475(9) . ?
O2 H2 0.8200 . ?
O2 C11 1.426(9) . ?
C3 C12 1.388(12) . ?
C3 C21 1.397(13) . ?
C4 C6 1.391(10) . ?
C4 C7 1.527(10) . ?
C4 C10 1.397(10) . ?
C5 C9 1.369(11) . ?
C5 C15 1.376(12) . ?
C6 H6 0.9300 . ?
C6 C9 1.383(10) . ?
C7 C8 1.563(10) . ?
C7 C11 1.545(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C18 1.503(11) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C15 1.390(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C17 1.395(13) . ?
C13 H13 0.9300 . ?
C13 C18 1.394(12) . ?
C13 C22 1.381(13) . ?
C14 H14 0.9300 . ?
C14 C18 1.370(11) . ?
C14 C19 1.426(13) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C20 1.529(14) . ?
C16 C28 1.561(13) . ?
C16 C30 1.558(13) . ?
C17 H17 0.9300 . ?
C17 C27 1.397(15) . ?
C19 H19 0.9300 . ?
C19 C32 1.367(13) . ?
C20 H20 0.9800 . ?
C20 C23 1.549(12) . ?
C20 C24 1.517(12) . ?
C21 H21 0.9300 . ?
C21 C26 1.386(13) . ?
C22 H22 0.9300 . ?
C22 C32 1.342(13) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C29 1.478(13) . ?
C24 H24 0.9800 . ?
C24 C31 1.539(12) . ?
C25 H25 0.9800 . ?
C25 C29 1.518(15) . ?
C25 C31 1.557(13) . ?
C25 C33 1.535(17) . ?
C26 H26 0.9300 . ?
C26 C27 1.365(14) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 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
O35 P1 C3 108.8(4) . . ?
O35 P1 C7 100.9(3) . . ?
C3 P1 C7 113.0(4) . . ?
O36 P1 O35 113.7(3) . . ?
O36 P1 C3 108.1(4) . . ?
O36 P1 C7 112.3(4) . . ?
C24 O35 P1 121.7(5) . . ?
C11 O2 H2 109.5 . . ?
C12 C3 P1 123.7(8) . . ?
C12 C3 C21 119.1(9) . . ?
C21 C3 P1 117.2(8) . . ?
C6 C4 C7 120.5(7) . . ?
C6 C4 C10 116.4(7) . . ?
C10 C4 C7 122.9(7) . . ?
C9 C5 Cl1 121.0(7) . . ?
C9 C5 C15 119.0(7) . . ?
C15 C5 Cl1 119.9(7) . . ?
C4 C6 H6 118.4 . . ?
C9 C6 C4 123.2(8) . . ?
C9 C6 H6 118.4 . . ?
C4 C7 P1 109.7(6) . . ?
C4 C7 C8 110.2(6) . . ?
C4 C7 C11 111.9(6) . . ?
C8 C7 P1 106.0(5) . . ?
C11 C7 P1 110.5(6) . . ?
C11 C7 C8 108.2(7) . . ?
C7 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C18 C8 C7 116.0(7) . . ?
C18 C8 H8A 108.3 . . ?
C18 C8 H8B 108.3 . . ?
C5 C9 C6 119.3(8) . . ?
C5 C9 H9 120.3 . . ?
C6 C9 H9 120.3 . . ?
C4 C10 H10 119.9 . . ?
C15 C10 C4 120.1(8) . . ?
C15 C10 H10 119.9 . . ?
O2 C11 C7 110.6(7) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C3 C12 H12 120.0 . . ?
C3 C12 C17 120.0(10) . . ?
C17 C12 H12 120.0 . . ?
C18 C13 H13 119.6 . . ?
C22 C13 H13 119.6 . . ?
C22 C13 C18 120.9(10) . . ?
C18 C14 H14 119.3 . . ?
C18 C14 C19 121.4(10) . . ?
C19 C14 H14 119.3 . . ?
C5 C15 C10 121.8(8) . . ?
C5 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
C20 C16 H16 107.0 . . ?
C20 C16 C28 112.7(9) . . ?
C20 C16 C30 112.7(9) . . ?
C28 C16 H16 107.0 . . ?
C30 C16 H16 107.0 . . ?
C30 C16 C28 110.1(9) . . ?
C12 C17 H17 120.3 . . ?
C12 C17 C27 119.5(11) . . ?
C27 C17 H17 120.3 . . ?
C13 C18 C8 122.0(8) . . ?
C14 C18 C8 119.5(8) . . ?
C14 C18 C13 118.5(9) . . ?
C14 C19 H19 121.9 . . ?
C32 C19 C14 116.2(10) . . ?
C32 C19 H19 121.9 . . ?
C16 C20 H20 106.5 . . ?
C16 C20 C23 114.6(8) . . ?
C23 C20 H20 106.5 . . ?
C24 C20 C16 113.6(8) . . ?
C24 C20 H20 106.5 . . ?
C24 C20 C23 108.5(8) . . ?
C3 C21 H21 119.6 . . ?
C26 C21 C3 120.9(11) . . ?
C26 C21 H21 119.6 . . ?
C13 C22 H22 120.6 . . ?
C32 C22 C13 118.9(11) . . ?
C32 C22 H22 120.6 . . ?
C20 C23 H23A 109.2 . . ?
C20 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C29 C23 C20 112.2(9) . . ?
C29 C23 H23A 109.2 . . ?
C29 C23 H23B 109.2 . . ?
O35 C24 C20 108.5(7) . . ?
O35 C24 H24 109.9 . . ?
O35 C24 C31 106.1(7) . . ?
C20 C24 H24 109.9 . . ?
C20 C24 C31 112.5(8) . . ?
C31 C24 H24 109.9 . . ?
C29 C25 H25 108.9 . . ?
C29 C25 C31 107.6(10) . . ?
C29 C25 C33 113.4(10) . . ?
C31 C25 H25 108.9 . . ?
C33 C25 H25 108.9 . . ?
C33 C25 C31 108.9(10) . . ?
C21 C26 H26 120.2 . . ?
C27 C26 C21 119.6(11) . . ?
C27 C26 H26 120.2 . . ?
C17 C27 H27 119.6 . . ?
C26 C27 C17 120.7(10) . . ?
C26 C27 H27 119.6 . . ?
C16 C28 H28A 109.5 . . ?
C16 C28 H28B 109.5 . . ?
C16 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 C25 115.2(9) . . ?
C23 C29 H29A 108.5 . . ?
C23 C29 H29B 108.5 . . ?
C25 C29 H29A 108.5 . . ?
C25 C29 H29B 108.5 . . ?
H29A C29 H29B 107.5 . . ?
C16 C30 H30A 109.5 . . ?
C16 C30 H30B 109.5 . . ?
C16 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C24 C31 C25 111.4(8) . . ?
C24 C31 H31A 109.3 . . ?
C24 C31 H31B 109.3 . . ?
C25 C31 H31A 109.3 . . ?
C25 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
C19 C32 H32 117.9 . . ?
C22 C32 C19 124.1(11) . . ?
C22 C32 H32 117.9 . . ?
C25 C33 H33A 109.5 . . ?
C25 C33 H33B 109.5 . . ?
C25 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
P1 O35 C24 C20 128.0(7) . . . . ?
P1 O35 C24 C31 -110.9(7) . . . . ?
P1 C3 C12 C17 178.0(8) . . . . ?
P1 C3 C21 C26 -178.4(8) . . . . ?
P1 C7 C8 C18 173.0(6) . . . . ?
P1 C7 C11 O2 -61.1(7) . . . . ?
Cl1 C5 C9 C6 178.7(7) . . . . ?
Cl1 C5 C15 C10 -179.4(7) . . . . ?
O35 P1 C3 C12 64.3(8) . . . . ?
O35 P1 C3 C21 -116.0(7) . . . . ?
O35 P1 C7 C4 -145.2(5) . . . . ?
O35 P1 C7 C8 95.8(5) . . . . ?
O35 P1 C7 C11 -21.3(6) . . . . ?
O35 C24 C31 C25 -176.3(8) . . . . ?
C3 P1 O35 C24 64.4(7) . . . . ?
C3 P1 C7 C4 -29.2(7) . . . . ?
C3 P1 C7 C8 -148.2(6) . . . . ?
C3 P1 C7 C11 94.8(6) . . . . ?
C3 C12 C17 C27 -1.0(15) . . . . ?
C3 C21 C26 C27 1.8(17) . . . . ?
C4 C6 C9 C5 3.2(13) . . . . ?
C4 C7 C8 C18 54.2(10) . . . . ?
C4 C7 C11 O2 61.5(9) . . . . ?
C4 C10 C15 C5 -1.7(14) . . . . ?
C6 C4 C7 P1 -51.3(10) . . . . ?
C6 C4 C7 C8 65.2(11) . . . . ?
C6 C4 C7 C11 -174.3(8) . . . . ?
C6 C4 C10 C15 3.1(13) . . . . ?
C7 P1 O35 C24 -176.6(6) . . . . ?
C7 P1 C3 C12 -46.9(9) . . . . ?
C7 P1 C3 C21 132.8(7) . . . . ?
C7 C4 C6 C9 -179.7(8) . . . . ?
C7 C4 C10 C15 178.8(8) . . . . ?
C7 C8 C18 C13 83.5(10) . . . . ?
C7 C8 C18 C14 -98.7(10) . . . . ?
C8 C7 C11 O2 -176.8(6) . . . . ?
C9 C5 C15 C10 0.8(14) . . . . ?
C10 C4 C6 C9 -3.9(13) . . . . ?
C10 C4 C7 P1 133.2(7) . . . . ?
C10 C4 C7 C8 -110.3(9) . . . . ?
C10 C4 C7 C11 10.2(12) . . . . ?
C11 C7 C8 C18 -68.5(9) . . . . ?
C12 C3 C21 C26 1.3(15) . . . . ?
C12 C17 C27 C26 4.2(18) . . . . ?
C13 C22 C32 C19 -1.1(17) . . . . ?
C14 C19 C32 C22 1.1(16) . . . . ?
C15 C5 C9 C6 -1.5(13) . . . . ?
C16 C20 C23 C29 177.7(9) . . . . ?
C16 C20 C24 O35 -58.7(10) . . . . ?
C16 C20 C24 C31 -175.8(8) . . . . ?
C18 C13 C22 C32 -0.3(15) . . . . ?
C18 C14 C19 C32 0.2(14) . . . . ?
C19 C14 C18 C8 -179.4(8) . . . . ?
C19 C14 C18 C13 -1.5(13) . . . . ?
C20 C23 C29 C25 56.6(13) . . . . ?
C20 C24 C31 C25 -57.8(11) . . . . ?
C21 C3 C12 C17 -1.7(14) . . . . ?
C21 C26 C27 C17 -4.5(18) . . . . ?
C22 C13 C18 C8 179.4(9) . . . . ?
C22 C13 C18 C14 1.6(14) . . . . ?
C23 C20 C24 O35 172.6(8) . . . . ?
C23 C20 C24 C31 55.6(11) . . . . ?
C24 C20 C23 C29 -54.2(12) . . . . ?
C28 C16 C20 C23 57.5(11) . . . . ?
C28 C16 C20 C24 -68.0(10) . . . . ?
C29 C25 C31 C24 53.8(12) . . . . ?
C30 C16 C20 C23 -68.0(11) . . . . ?
C30 C16 C20 C24 166.6(8) . . . . ?
C31 C25 C29 C23 -54.8(13) . . . . ?
C33 C25 C29 C23 -175.3(9) . . . . ?
C33 C25 C31 C24 177.1(9) . . . . ?
O36 P1 O35 C24 -56.1(7) . . . . ?
O36 P1 C3 C12 -171.8(7) . . . . ?
O36 P1 C3 C21 7.9(8) . . . . ?
O36 P1 C7 C4 93.4(6) . . . . ?
O36 P1 C7 C8 -25.6(6) . . . . ?
O36 P1 C7 C11 -142.7(5) . . . . ?

_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_221102h
_database_code_depnum_ccdc_archive 'CCDC 2217203'
loop_
_audit_author_name
_audit_author_address
'zhu lin'
;Liaocheng university
China
;
_audit_update_record             
;
2022-11-03 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-11-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H27 O P'
_chemical_formula_sum            'C18 H27 O P'
_chemical_formula_weight         290.36
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.3136(8)
_cell_length_b                   10.1805(9)
_cell_length_c                   9.9531(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.262(4)
_cell_angle_gamma                90
_cell_volume                     879.49(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      27.510
_cell_measurement_theta_min      2.346
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.1267
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4105
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.346
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.839
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                1773
_reflns_number_total             2842
_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 V6.36A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V6.36A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0873
_refine_ls_restrained_S_all      1.102
_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)+1.1850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1846
_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. Restrained distances
 C25-C24
 1.52 with sigma of 0.02
 C6-C2
 1.37 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C7(H7), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C24(H24A,H24B), C25(H25A,H25B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C21(H21), C22(H22), C23(H23)
3.d X=CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.0147(2) 0.1588(2) 0.9527(2) 0.0401(6) Uani 1 1 d . . . . .
C1 C 0.6933(9) 0.1519(14) 0.8338(9) 0.054(2) Uani 1 1 d . . . . .
H1 H 0.699686 0.062495 0.871944 0.065 Uiso 1 1 calc R U . . .
C2 C 1.1271(11) 0.1718(18) 0.5990(12) 0.084(4) Uani 1 1 d D . . . .
H2 H 1.143525 0.111233 0.536109 0.101 Uiso 1 1 calc R U . . .
C3 C 0.6937(10) 0.1404(13) 0.6822(10) 0.062(3) Uani 1 1 d . . . . .
H3 H 0.796241 0.109302 0.690931 0.075 Uiso 1 1 calc R U . . .
C5 C 1.2495(11) 0.1639(15) 1.2059(10) 0.079(3) Uani 1 1 d . . . . .
H5A H 1.246534 0.072700 1.199765 0.095 Uiso 1 1 calc R U . . .
H5B H 1.321807 0.204967 1.285142 0.095 Uiso 1 1 calc R U . . .
C6 C 1.1381(14) 0.3022(15) 0.5749(14) 0.083(4) Uani 1 1 d D . . . .
H6 H 1.161160 0.330292 0.496147 0.100 Uiso 1 1 calc R U . . .
C7 C 0.8311(9) 0.2287(9) 0.9378(9) 0.044(2) Uani 1 1 d . . . . .
H7 H 0.826515 0.318468 0.900946 0.052 Uiso 1 1 calc R U . . .
C9 C 1.0918(9) 0.1262(9) 0.7159(11) 0.056(3) Uani 1 1 d . . . . .
H9 H 1.085857 0.036710 0.731621 0.067 Uiso 1 1 calc R U . . .
C10 C 1.0659(10) 0.2172(11) 0.8072(10) 0.050(3) Uani 1 1 d . . . . .
C12 C 0.6688(16) 0.2687(15) 0.6042(12) 0.109(5) Uani 1 1 d . . . . .
H12A H 0.565941 0.299104 0.586522 0.164 Uiso 1 1 calc R U . . .
H12B H 0.682972 0.257491 0.514070 0.164 Uiso 1 1 calc R U . . .
H12C H 0.741429 0.332071 0.661931 0.164 Uiso 1 1 calc R U . . .
C13 C 0.5790(13) 0.0381(14) 0.5958(12) 0.099(5) Uani 1 1 d . . . . .
H13A H 0.597589 -0.043187 0.648092 0.148 Uiso 1 1 calc R U . . .
H13B H 0.590691 0.025123 0.504719 0.148 Uiso 1 1 calc R U . . .
H13C H 0.476272 0.067743 0.579699 0.148 Uiso 1 1 calc R U . . .
C15 C 0.6702(15) 0.2932(16) 1.2390(14) 0.118(6) Uani 1 1 d . . . . .
H15A H 0.674180 0.204299 1.272355 0.177 Uiso 1 1 calc R U . . .
H15B H 0.577248 0.334230 1.238702 0.177 Uiso 1 1 calc R U . . .
H15C H 0.757683 0.340837 1.301907 0.177 Uiso 1 1 calc R U . . .
C17 C 0.6723(13) 0.2935(14) 1.0881(12) 0.081(4) Uani 1 1 d . . . . .
H17 H 0.664187 0.384609 1.054323 0.097 Uiso 1 1 calc R U . . .
C18 C 0.8240(11) 0.2363(10) 1.0877(9) 0.055(3) Uani 1 1 d . . . . .
H18A H 0.908553 0.290144 1.148415 0.066 Uiso 1 1 calc R U . . .
H18B H 0.837296 0.148772 1.129049 0.066 Uiso 1 1 calc R U . . .
O20 O 1.0165(8) 0.0141(6) 0.9609(7) 0.064(2) Uani 1 1 d . . . . .
C21 C 1.1546(10) 0.2325(10) 1.1058(10) 0.051(3) Uani 1 1 d . . . . .
H21 H 1.158743 0.323620 1.113233 0.062 Uiso 1 1 calc R U . . .
C22 C 1.0786(12) 0.3476(11) 0.7820(12) 0.061(3) Uani 1 1 d . . . . .
H22 H 1.061906 0.408708 0.844281 0.073 Uiso 1 1 calc R U . . .
C23 C 1.1150(14) 0.3919(14) 0.6679(13) 0.082(4) Uani 1 1 d . . . . .
H23 H 1.123822 0.481423 0.653947 0.098 Uiso 1 1 calc R U . . .
C24 C 0.5441(11) 0.2127(13) 0.8380(12) 0.089(5) Uani 1 1 d D . . . .
H24A H 0.534200 0.301359 0.800078 0.107 Uiso 1 1 calc R U . . .
H24B H 0.457097 0.162205 0.775681 0.107 Uiso 1 1 calc R U . . .
C25 C 0.5382(13) 0.2169(16) 0.9863(14) 0.111(6) Uani 1 1 d D . . . .
H25A H 0.540464 0.128020 1.022168 0.134 Uiso 1 1 calc R U . . .
H25B H 0.442455 0.257441 0.982168 0.134 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 C7 1.808(9) . ?
P1 C10 1.783(10) . ?
P1 O20 1.475(6) . ?
P1 C21 1.772(9) . ?
C1 H1 0.9800 . ?
C1 C3 1.514(12) . ?
C1 C7 1.539(12) . ?
C1 C24 1.535(13) . ?
C2 H2 0.9300 . ?
C2 C6 1.360(16) . ?
C2 C9 1.397(15) . ?
C3 H3 0.9800 . ?
C3 C12 1.494(16) . ?
C3 C13 1.516(14) . ?
C5 H5A 0.9300 . ?
C5 H5B 0.9300 . ?
C5 C21 1.275(12) . ?
C6 H6 0.9300 . ?
C6 C23 1.372(17) . ?
C7 H7 0.9800 . ?
C7 C18 1.519(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(12) . ?
C10 C22 1.364(13) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C17 1.509(14) . ?
C17 H17 0.9800 . ?
C17 C18 1.529(13) . ?
C17 C25 1.509(16) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.374(14) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.498(14) . ?
C25 H25A 0.9700 . ?
C25 H25B 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
C10 P1 C7 109.0(4) . . ?
O20 P1 C7 112.9(4) . . ?
O20 P1 C10 112.1(5) . . ?
O20 P1 C21 112.7(5) . . ?
C21 P1 C7 106.4(4) . . ?
C21 P1 C10 103.2(4) . . ?
C3 C1 H1 107.0 . . ?
C3 C1 C7 114.0(8) . . ?
C3 C1 C24 112.8(8) . . ?
C7 C1 H1 107.0 . . ?
C24 C1 H1 107.0 . . ?
C24 C1 C7 108.6(9) . . ?
C6 C2 H2 119.1 . . ?
C6 C2 C9 121.8(12) . . ?
C9 C2 H2 119.1 . . ?
C1 C3 H3 106.9 . . ?
C1 C3 C13 111.3(10) . . ?
C12 C3 C1 113.2(12) . . ?
C12 C3 H3 106.9 . . ?
C12 C3 C13 111.2(9) . . ?
C13 C3 H3 106.9 . . ?
H5A C5 H5B 120.0 . . ?
C21 C5 H5A 120.0 . . ?
C21 C5 H5B 120.0 . . ?
C2 C6 H6 120.3 . . ?
C2 C6 C23 119.4(12) . . ?
C23 C6 H6 120.3 . . ?
P1 C7 H7 108.0 . . ?
C1 C7 P1 112.9(7) . . ?
C1 C7 H7 108.0 . . ?
C18 C7 P1 108.4(6) . . ?
C18 C7 C1 111.3(7) . . ?
C18 C7 H7 108.0 . . ?
C2 C9 H9 120.8 . . ?
C10 C9 C2 118.4(10) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 P1 118.3(8) . . ?
C22 C10 P1 122.7(8) . . ?
C22 C10 C9 119.0(9) . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C15 H15A 109.5 . . ?
C17 C15 H15B 109.5 . . ?
C17 C15 H15C 109.5 . . ?
C15 C17 H17 108.4 . . ?
C15 C17 C18 110.3(10) . . ?
C15 C17 C25 111.1(10) . . ?
C18 C17 H17 108.4 . . ?
C25 C17 H17 108.4 . . ?
C25 C17 C18 110.0(10) . . ?
C7 C18 C17 113.0(8) . . ?
C7 C18 H18A 109.0 . . ?
C7 C18 H18B 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
P1 C21 H21 119.2 . . ?
C5 C21 P1 121.7(9) . . ?
C5 C21 H21 119.2 . . ?
C10 C22 H22 118.8 . . ?
C10 C22 C23 122.3(12) . . ?
C23 C22 H22 118.8 . . ?
C6 C23 C22 119.0(13) . . ?
C6 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C1 C24 H24A 108.9 . . ?
C1 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C1 113.3(9) . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C17 C25 H25A 109.4 . . ?
C17 C25 H25B 109.4 . . ?
C24 C25 C17 111.1(10) . . ?
C24 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?

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 C18 C17 -179.7(8) . . . . ?
P1 C10 C22 C23 -178.6(8) . . . . ?
C1 C7 C18 C17 -54.9(12) . . . . ?
C1 C24 C25 C17 58.1(15) . . . . ?
C2 C6 C23 C22 -1.1(19) . . . . ?
C2 C9 C10 P1 178.0(7) . . . . ?
C2 C9 C10 C22 -1.2(13) . . . . ?
C3 C1 C7 P1 -57.6(12) . . . . ?
C3 C1 C7 C18 -179.8(10) . . . . ?
C3 C1 C24 C25 176.4(11) . . . . ?
C6 C2 C9 C10 0.8(15) . . . . ?
C7 P1 C10 C9 -122.1(7) . . . . ?
C7 P1 C10 C22 57.1(9) . . . . ?
C7 P1 C21 C5 127.7(9) . . . . ?
C7 C1 C3 C12 -67.6(12) . . . . ?
C7 C1 C3 C13 166.4(9) . . . . ?
C7 C1 C24 C25 -56.2(13) . . . . ?
C9 C2 C6 C23 0.4(19) . . . . ?
C9 C10 C22 C23 0.5(16) . . . . ?
C10 P1 C7 C1 83.4(7) . . . . ?
C10 P1 C7 C18 -152.8(6) . . . . ?
C10 P1 C21 C5 -117.6(9) . . . . ?
C10 C22 C23 C6 0.6(18) . . . . ?
C15 C17 C18 C7 177.7(10) . . . . ?
C15 C17 C25 C24 -177.7(11) . . . . ?
C18 C17 C25 C24 -55.2(15) . . . . ?
O20 P1 C7 C1 -41.9(8) . . . . ?
O20 P1 C7 C18 81.9(7) . . . . ?
O20 P1 C10 C9 3.7(8) . . . . ?
O20 P1 C10 C22 -177.1(8) . . . . ?
O20 P1 C21 C5 3.5(10) . . . . ?
C21 P1 C7 C1 -166.0(7) . . . . ?
C21 P1 C7 C18 -42.1(7) . . . . ?
C21 P1 C10 C9 125.1(7) . . . . ?
C21 P1 C10 C22 -55.7(9) . . . . ?
C24 C1 C3 C12 56.9(13) . . . . ?
C24 C1 C3 C13 -69.1(14) . . . . ?
C24 C1 C7 P1 175.7(8) . . . . ?
C24 C1 C7 C18 53.4(11) . . . . ?
C25 C17 C18 C7 54.8(13) . . . . ?

_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_220605d
_database_code_depnum_ccdc_archive 'CCDC 2216573'
loop_
_audit_author_name
_audit_author_address
lin
; Liaocheng university
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H38 Cl O2 P'
_chemical_formula_sum            'C27 H38 Cl O2 P'
_chemical_formula_weight         460.99
_chemical_absolute_configuration multi-scan
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.7102(11)
_cell_length_b                   5.9519(5)
_cell_length_c                   18.9788(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.214(2)
_cell_angle_gamma                90
_cell_volume                     1417.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1237
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      23.552
_cell_measurement_theta_min      2.094
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.1211
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6843
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.093
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                2203
_reflns_number_total             4720
_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 v6.02A (Bruker, 2001)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4720
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1743
_refine_ls_R_factor_gt           0.1149
_refine_ls_restrained_S_all      0.989
_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)+(0.1807P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2925
_refine_ls_wR_factor_ref         0.3311
_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 Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C10(H10), C14(H14), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C19(H19A,H19B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C17(H17), C23(H23),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C26(H26A,H26B,
 H26C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.7241(2) -1.0508(6) -0.21095(15) 0.0742(9) Uani 1 1 d . . . . .
Cl1 Cl -0.8525(4) -0.8750(11) 0.1204(2) 0.1426(18) Uani 1 1 d . . . . .
O31 O -0.7093(6) -0.9979(13) -0.2910(4) 0.079(2) Uani 1 1 d . . . . .
C1 C -0.8852(9) -1.051(3) -0.0868(7) 0.093(3) Uani 1 1 d . . . . .
H1 H -0.9112 -1.1747 -0.1139 0.112 Uiso 1 1 calc R U . . .
O2 O -0.7442(6) -1.2954(14) -0.1973(4) 0.082(2) Uani 1 1 d . . . . .
C3 C -0.6805(9) -1.084(2) -0.4120(6) 0.081(3) Uani 1 1 d . . . . .
H3 H -0.6364 -0.9491 -0.4128 0.097 Uiso 1 1 calc R U . . .
C4 C -0.8149(10) -0.681(3) -0.0021(8) 0.099(4) Uani 1 1 d . . . . .
H4 H -0.7924 -0.5552 0.0254 0.119 Uiso 1 1 calc R U . . .
C5 C -0.8114(9) -0.682(2) -0.0768(7) 0.082(3) Uani 1 1 d . . . . .
H5 H -0.7861 -0.5562 -0.0978 0.099 Uiso 1 1 calc R U . . .
C6 C -0.8350(8) -0.869(2) -0.1983(6) 0.071(3) Uani 1 1 d . . . . .
H6 H -0.8176 -0.7159 -0.2114 0.085 Uiso 1 1 calc R U . . .
C7 C -1.0333(11) -0.783(4) -0.2529(9) 0.121(6) Uani 1 1 d . . . . .
H7 H -1.0443 -0.7515 -0.2039 0.145 Uiso 1 1 calc R U . . .
C8 C -0.8867(10) -1.049(3) -0.0120(7) 0.097(4) Uani 1 1 d . . . . .
H8 H -0.9119 -1.1739 0.0097 0.116 Uiso 1 1 calc R U . . .
C9 C -0.9383(9) -0.944(2) -0.2491(7) 0.088(4) Uani 1 1 d . . . . .
H9A H -0.9213 -0.9612 -0.2969 0.105 Uiso 1 1 calc R U . . .
H9B H -0.9597 -1.0897 -0.2337 0.105 Uiso 1 1 calc R U . . .
C10 C -0.7960(10) -1.015(3) -0.4430(7) 0.098(4) Uani 1 1 d . . . . .
H10 H -0.8172 -0.9038 -0.4098 0.117 Uiso 1 1 calc R U . . .
C11 C -0.6320(11) -1.265(3) -0.4558(8) 0.108(5) Uani 1 1 d . . . . .
H11A H -0.6720 -1.4037 -0.4549 0.129 Uiso 1 1 calc R U . . .
H11B H -0.6387 -1.2163 -0.5051 0.129 Uiso 1 1 calc R U . . .
C12 C -0.8454(8) -0.869(2) -0.1194(6) 0.077(3) Uani 1 1 d . . . . .
C13 C -0.6049(9) -0.9448(19) -0.1556(6) 0.070(3) Uani 1 1 d . . . . .
C14 C -0.4977(12) -1.380(4) -0.3490(8) 0.131(6) Uani 1 1 d . . . . .
H14 H -0.5355 -1.5220 -0.3460 0.157 Uiso 1 1 calc R U . . .
C15 C -0.5609(10) -0.735(2) -0.1699(7) 0.088(4) Uani 1 1 d . . . . .
H15 H -0.5957 -0.6448 -0.2064 0.106 Uiso 1 1 calc R U . . .
C16 C -0.5536(10) -1.071(3) -0.1001(6) 0.102(4) Uani 1 1 d . . . . .
H16 H -0.5817 -1.2097 -0.0902 0.122 Uiso 1 1 calc R U . . .
C17 C -0.4579(12) -0.994(3) -0.0575(7) 0.106(4) Uani 1 1 d . . . . .
H17 H -0.4251 -1.0788 -0.0190 0.127 Uiso 1 1 calc R U . . .
C18 C -0.8513(10) -0.865(3) 0.0284(7) 0.090(4) Uani 1 1 d . . . . .
C19 C -0.5460(10) -1.212(3) -0.3054(6) 0.102(4) Uani 1 1 d . . . . .
H19A H -0.5069 -1.0718 -0.3048 0.122 Uiso 1 1 calc R U . . .
H19B H -0.5392 -1.2657 -0.2567 0.122 Uiso 1 1 calc R U . . .
C20 C -0.8025(13) -0.893(4) -0.5158(7) 0.145(7) Uani 1 1 d . . . . .
H20A H -0.7418 -0.7960 -0.5148 0.217 Uiso 1 1 calc R U . . .
H20B H -0.8666 -0.8046 -0.5246 0.217 Uiso 1 1 calc R U . . .
H20C H -0.8032 -1.0017 -0.5532 0.217 Uiso 1 1 calc R U . . .
C21 C -0.8761(12) -1.207(5) -0.4457(11) 0.175(9) Uani 1 1 d . . . . .
H21A H -0.8722 -1.2993 -0.4867 0.263 Uiso 1 1 calc R U . . .
H21B H -0.9467 -1.1470 -0.4487 0.263 Uiso 1 1 calc R U . . .
H21C H -0.8597 -1.2965 -0.4032 0.263 Uiso 1 1 calc R U . . .
C22 C -0.3774(14) -1.423(4) -0.3196(9) 0.185(12) Uani 1 1 d . . . . .
H22A H -0.3362 -1.2945 -0.3292 0.278 Uiso 1 1 calc R U . . .
H22B H -0.3535 -1.5529 -0.3424 0.278 Uiso 1 1 calc R U . . .
H22C H -0.3686 -1.4477 -0.2690 0.278 Uiso 1 1 calc R U . . .
C23 C -0.4141(12) -0.790(3) -0.0742(8) 0.108(5) Uani 1 1 d . . . . .
H23 H -0.3502 -0.7405 -0.0481 0.129 Uiso 1 1 calc R U . . .
C24 C -0.4657(11) -0.662(3) -0.1295(8) 0.110(4) Uani 1 1 d . . . . .
H24 H -0.4366 -0.5253 -0.1402 0.132 Uiso 1 1 calc R U . . .
C25 C -0.5143(12) -1.311(4) -0.4270(7) 0.121(6) Uani 1 1 d . . . . .
H25A H -0.4884 -1.4288 -0.4549 0.146 Uiso 1 1 calc R U . . .
H25B H -0.4732 -1.1760 -0.4321 0.146 Uiso 1 1 calc R U . . .
C26 C -1.1369(12) -0.895(4) -0.2930(11) 0.172(9) Uani 1 1 d . . . . .
H26A H -1.1293 -0.9216 -0.3418 0.258 Uiso 1 1 calc R U . . .
H26B H -1.1966 -0.7978 -0.2913 0.258 Uiso 1 1 calc R U . . .
H26C H -1.1485 -1.0357 -0.2705 0.258 Uiso 1 1 calc R U . . .
C32 C -0.6636(8) -1.168(3) -0.3338(6) 0.081(3) Uani 1 1 d . . . . .
H32 H -0.7031 -1.3084 -0.3319 0.098 Uiso 1 1 calc R U . . .
C2 C -1.0166(17) -0.570(4) -0.2867(13) 0.193(11) Uani 1 1 d . . . . .
H2A H -0.9883 -0.4625 -0.2509 0.289 Uiso 1 1 calc R U . . .
H2B H -1.0832 -0.5162 -0.3121 0.289 Uiso 1 1 calc R U . . .
H2C H -0.9671 -0.5904 -0.3195 0.289 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 O31 1.592(7) . ?
P1 O2 1.508(8) . ?
P1 C6 1.823(11) . ?
P1 C13 1.812(12) . ?
Cl1 C18 1.750(13) . ?
O31 C32 1.473(14) . ?
C1 H1 0.9300 . ?
C1 C8 1.424(18) . ?
C1 C12 1.382(19) . ?
C3 H3 0.9800 . ?
C3 C10 1.548(17) . ?
C3 C11 1.548(18) . ?
C3 C32 1.548(15) . ?
C4 H4 0.9300 . ?
C4 C5 1.427(18) . ?
C4 C18 1.354(19) . ?
C5 H5 0.9300 . ?
C5 C12 1.401(18) . ?
C6 H6 0.9800 . ?
C6 C9 1.565(16) . ?
C6 C12 1.523(15) . ?
C7 H7 0.9800 . ?
C7 C9 1.533(18) . ?
C7 C26 1.56(2) . ?
C7 C2 1.45(3) . ?
C8 H8 0.9300 . ?
C8 C18 1.37(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9800 . ?
C10 C20 1.55(2) . ?
C10 C21 1.53(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C25 1.532(17) . ?
C13 C15 1.412(16) . ?
C13 C16 1.371(17) . ?
C14 H14 0.9800 . ?
C14 C19 1.49(2) . ?
C14 C22 1.56(2) . ?
C14 C25 1.518(19) . ?
C15 H15 0.9300 . ?
C15 C24 1.394(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.424(19) . ?
C17 H17 0.9300 . ?
C17 C23 1.39(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C32 1.528(15) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.38(2) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C32 H32 0.9800 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
O31 P1 C6 102.8(4) . . ?
O31 P1 C13 105.6(5) . . ?
O2 P1 O31 113.8(4) . . ?
O2 P1 C6 113.2(5) . . ?
O2 P1 C13 112.7(5) . . ?
C13 P1 C6 108.0(5) . . ?
C32 O31 P1 120.5(7) . . ?
C8 C1 H1 119.8 . . ?
C12 C1 H1 119.8 . . ?
C12 C1 C8 120.4(14) . . ?
C10 C3 H3 106.6 . . ?
C10 C3 C11 114.6(10) . . ?
C10 C3 C32 115.3(9) . . ?
C11 C3 H3 106.6 . . ?
C11 C3 C32 106.6(11) . . ?
C32 C3 H3 106.6 . . ?
C5 C4 H4 120.4 . . ?
C18 C4 H4 120.4 . . ?
C18 C4 C5 119.2(14) . . ?
C4 C5 H5 119.3 . . ?
C12 C5 C4 121.5(12) . . ?
C12 C5 H5 119.3 . . ?
P1 C6 H6 107.9 . . ?
C9 C6 P1 109.9(8) . . ?
C9 C6 H6 107.9 . . ?
C12 C6 P1 108.7(7) . . ?
C12 C6 H6 107.9 . . ?
C12 C6 C9 114.2(8) . . ?
C9 C7 H7 107.8 . . ?
C9 C7 C26 110.5(16) . . ?
C26 C7 H7 107.8 . . ?
C2 C7 H7 107.8 . . ?
C2 C7 C9 113.3(16) . . ?
C2 C7 C26 109.3(16) . . ?
C1 C8 H8 119.8 . . ?
C18 C8 C1 120.4(14) . . ?
C18 C8 H8 119.8 . . ?
C6 C9 H9A 108.4 . . ?
C6 C9 H9B 108.4 . . ?
C7 C9 C6 115.4(11) . . ?
C7 C9 H9A 108.4 . . ?
C7 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C3 C10 H10 106.0 . . ?
C3 C10 C20 112.1(10) . . ?
C20 C10 H10 106.0 . . ?
C21 C10 C3 113.5(15) . . ?
C21 C10 H10 106.0 . . ?
C21 C10 C20 112.5(14) . . ?
C3 C11 H11A 109.1 . . ?
C3 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C25 C11 C3 112.3(11) . . ?
C25 C11 H11A 109.1 . . ?
C25 C11 H11B 109.1 . . ?
C1 C12 C5 117.6(11) . . ?
C1 C12 C6 122.3(12) . . ?
C5 C12 C6 120.0(11) . . ?
C15 C13 P1 121.1(9) . . ?
C16 C13 P1 120.3(10) . . ?
C16 C13 C15 118.5(12) . . ?
C19 C14 H14 107.3 . . ?
C19 C14 C22 112.2(14) . . ?
C19 C14 C25 110.7(13) . . ?
C22 C14 H14 107.3 . . ?
C25 C14 H14 107.3 . . ?
C25 C14 C22 111.6(13) . . ?
C13 C15 H15 119.8 . . ?
C24 C15 C13 120.4(12) . . ?
C24 C15 H15 119.8 . . ?
C13 C16 H16 119.4 . . ?
C13 C16 C17 121.2(15) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.4 . . ?
C23 C17 C16 119.2(14) . . ?
C23 C17 H17 120.4 . . ?
C4 C18 Cl1 120.8(12) . . ?
C4 C18 C8 120.8(12) . . ?
C8 C18 Cl1 118.3(12) . . ?
C14 C19 H19A 109.0 . . ?
C14 C19 H19B 109.0 . . ?
C14 C19 C32 112.8(12) . . ?
H19A C19 H19B 107.8 . . ?
C32 C19 H19A 109.0 . . ?
C32 C19 H19B 109.0 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C21 H21A 109.5 . . ?
C10 C21 H21B 109.5 . . ?
C10 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23 120.1 . . ?
C24 C23 C17 119.8(14) . . ?
C24 C23 H23 120.1 . . ?
C15 C24 H24 119.6 . . ?
C23 C24 C15 120.9(15) . . ?
C23 C24 H24 119.6 . . ?
C11 C25 H25A 109.2 . . ?
C11 C25 H25B 109.2 . . ?
C14 C25 C11 111.8(12) . . ?
C14 C25 H25A 109.2 . . ?
C14 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C7 C26 H26A 109.5 . . ?
C7 C26 H26B 109.5 . . ?
C7 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O31 C32 C3 107.6(10) . . ?
O31 C32 C19 111.9(9) . . ?
O31 C32 H32 108.5 . . ?
C3 C32 H32 108.5 . . ?
C19 C32 C3 111.8(9) . . ?
C19 C32 H32 108.5 . . ?
C7 C2 H2A 109.5 . . ?
C7 C2 H2B 109.5 . . ?
C7 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
P1 O31 C32 C3 169.0(7) . . . . ?
P1 O31 C32 C19 -67.8(12) . . . . ?
P1 C6 C9 C7 -170.5(11) . . . . ?
P1 C6 C12 C1 -73.3(11) . . . . ?
P1 C6 C12 C5 105.0(11) . . . . ?
P1 C13 C15 C24 -176.0(10) . . . . ?
P1 C13 C16 C17 177.9(10) . . . . ?
O31 P1 C6 C9 64.6(8) . . . . ?
O31 P1 C6 C12 -169.6(8) . . . . ?
O31 P1 C13 C15 42.6(10) . . . . ?
O31 P1 C13 C16 -135.3(10) . . . . ?
C1 C8 C18 Cl1 -178.7(9) . . . . ?
C1 C8 C18 C4 0(2) . . . . ?
O2 P1 O31 C32 -30.3(9) . . . . ?
O2 P1 C6 C9 -58.6(9) . . . . ?
O2 P1 C6 C12 67.1(9) . . . . ?
O2 P1 C13 C15 167.4(8) . . . . ?
O2 P1 C13 C16 -10.5(11) . . . . ?
C3 C11 C25 C14 56.8(19) . . . . ?
C4 C5 C12 C1 1.7(17) . . . . ?
C4 C5 C12 C6 -176.7(10) . . . . ?
C5 C4 C18 Cl1 177.7(9) . . . . ?
C5 C4 C18 C8 -1.4(19) . . . . ?
C6 P1 O31 C32 -153.1(8) . . . . ?
C6 P1 C13 C15 -66.8(10) . . . . ?
C6 P1 C13 C16 115.3(10) . . . . ?
C8 C1 C12 C5 -2.7(17) . . . . ?
C8 C1 C12 C6 175.6(10) . . . . ?
C9 C6 C12 C1 49.9(15) . . . . ?
C9 C6 C12 C5 -131.8(11) . . . . ?
C10 C3 C11 C25 174.4(13) . . . . ?
C10 C3 C32 O31 -51.6(14) . . . . ?
C10 C3 C32 C19 -174.8(13) . . . . ?
C11 C3 C10 C20 -66.3(18) . . . . ?
C11 C3 C10 C21 62.5(15) . . . . ?
C11 C3 C32 O31 -179.9(9) . . . . ?
C11 C3 C32 C19 56.8(14) . . . . ?
C12 C1 C8 C18 1.8(18) . . . . ?
C12 C6 C9 C7 66.9(15) . . . . ?
C13 P1 O31 C32 93.8(8) . . . . ?
C13 P1 C6 C9 175.9(8) . . . . ?
C13 P1 C6 C12 -58.3(9) . . . . ?
C13 C15 C24 C23 -2(2) . . . . ?
C13 C16 C17 C23 -2(2) . . . . ?
C14 C19 C32 O31 -178.7(12) . . . . ?
C14 C19 C32 C3 -58.0(17) . . . . ?
C15 C13 C16 C17 0.0(19) . . . . ?
C16 C13 C15 C24 1.9(18) . . . . ?
C16 C17 C23 C24 3(2) . . . . ?
C17 C23 C24 C15 -1(2) . . . . ?
C18 C4 C5 C12 0.3(18) . . . . ?
C19 C14 C25 C11 -53(2) . . . . ?
C22 C14 C19 C32 179.8(16) . . . . ?
C22 C14 C25 C11 -179.3(17) . . . . ?
C25 C14 C19 C32 54.3(19) . . . . ?
C26 C7 C9 C6 -169.0(13) . . . . ?
C32 C3 C10 C20 169.4(14) . . . . ?
C32 C3 C10 C21 -61.8(16) . . . . ?
C32 C3 C11 C25 -56.8(14) . . . . ?
C2 C7 C9 C6 68.0(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
