# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_210112f
_database_code_depnum_ccdc_archive 'CCDC 2070968'
loop_
_audit_author_name
_audit_author_address
'Zhan-Cai Li'
;Liaocheng University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-03-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 O2 P'
_chemical_formula_sum            'C22 H16 O2 P'
_chemical_formula_weight         343.32
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.572(14)
_cell_length_b                   11.144(14)
_cell_length_c                   15.98(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.132(19)
_cell_angle_gamma                90
_cell_volume                     1799(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    903
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.904
_cell_measurement_theta_min      2.257
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.164
_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    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_unetI/netI     0.1892
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3174
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_v_R_equivalents   ?
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1525
_reflns_number_total             3174
_reflns_special_details          
;
 _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         0.851
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2350
_refine_ls_R_factor_gt           0.1503
_refine_ls_restrained_S_all      1.097
_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)+(0.1756P)²+5.2455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3947
_refine_ls_wR_factor_ref         0.4322
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.605(14)
 0.395(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C9(H9), C11(H11), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
3.b 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 0.7191(3) 0.8640(2) 0.24600(18) 0.0456(9) Uani 1 1 d . . . . .
O1 O 0.6569(7) 0.9533(6) 0.2924(5) 0.056(2) Uani 1 1 d . . . . .
O2 O 0.8991(7) 0.6749(6) 0.2027(5) 0.059(2) Uani 1 1 d . . . . .
H2 H 0.8524 0.7324 0.1813 0.088 Uiso 1 1 calc R U . . .
C3 C 0.3809(10) 0.6575(9) 0.0526(6) 0.043(2) Uani 1 1 d . . . . .
C4 C 0.5933(10) 0.7787(9) 0.1713(6) 0.040(2) Uani 1 1 d . . . . .
C5 C 0.4749(10) 0.7733(10) 0.1876(7) 0.051(3) Uani 1 1 d . . . . .
H5 H 0.4651 0.8091 0.2379 0.061 Uiso 1 1 calc R U . . .
C6 C 1.0361(10) 0.8352(9) 0.2729(7) 0.050(3) Uani 1 1 d . . . . .
C7 C 0.7497(12) 1.0168(9) 0.1228(7) 0.056(3) Uani 1 1 d . . . . .
H7 H 0.6585 1.0243 0.1112 0.067 Uiso 1 1 calc R U . . .
C8 C 1.0201(13) 0.9922(11) 0.1604(10) 0.073(4) Uani 1 1 d . . . . .
H8 H 1.1115 0.9855 0.1730 0.087 Uiso 1 1 calc R U . . .
C9 C 0.5049(11) 0.6649(10) 0.0391(7) 0.053(3) Uani 1 1 d . . . . .
H9 H 0.5177 0.6282 -0.0101 0.064 Uiso 1 1 calc R U . . .
C10 C 0.9546(10) 0.9219(8) 0.2046(7) 0.044(2) Uani 1 1 d . . . . .
C11 C 1.1498(11) 0.8754(10) 0.3351(8) 0.058(3) Uani 1 1 d . . . . .
H11 H 1.1735 0.9560 0.3369 0.069 Uiso 1 1 calc R U . . .
C12 C 0.3624(10) 0.7125(9) 0.1278(7) 0.047(3) Uani 1 1 d . . . . .
C13 C 1.0058(10) 0.7136(9) 0.2679(7) 0.048(3) Uani 1 1 d . . . . .
C14 C 0.8189(10) 0.9342(8) 0.1864(7) 0.044(2) Uani 1 1 d . . . . .
C15 C 1.0859(11) 0.6351(10) 0.3266(7) 0.056(3) Uani 1 1 d . . . . .
H15 H 1.0654 0.5538 0.3235 0.067 Uiso 1 1 calc R U . . .
C16 C 0.6081(11) 0.7240(10) 0.0954(7) 0.052(3) Uani 1 1 d . . . . .
H16 H 0.6890 0.7282 0.0835 0.062 Uiso 1 1 calc R U . . .
C17 C 0.2697(12) 0.6031(10) -0.0063(7) 0.057(3) Uani 1 1 d . . . . .
H17 H 0.2790 0.5659 -0.0562 0.069 Uiso 1 1 calc R U . . .
C18 C 0.8147(14) 1.0869(12) 0.0771(9) 0.070(3) Uani 1 1 d . . . . .
H18 H 0.7679 1.1408 0.0348 0.084 Uiso 1 1 calc R U . . .
C19 C 0.9499(16) 1.0755(12) 0.0952(9) 0.081(4) Uani 1 1 d . . . . .
H19 H 0.9953 1.1220 0.0652 0.097 Uiso 1 1 calc R U . . .
C20 C 0.2376(11) 0.7094(10) 0.1427(8) 0.059(3) Uani 1 1 d . . . . .
H20 H 0.2266 0.7433 0.1933 0.071 Uiso 1 1 calc R U . . .
C21 C 0.1499(12) 0.6037(11) 0.0077(8) 0.062(3) Uani 1 1 d . . . . .
H21 H 0.0779 0.5687 -0.0332 0.075 Uiso 1 1 calc R U . . .
C22 C 0.1329(13) 0.6565(13) 0.0829(9) 0.077(4) Uani 1 1 d . . . . .
H22 H 0.0502 0.6555 0.0923 0.093 Uiso 1 1 calc R U . . .
C23 C 1.2276(12) 0.7954(12) 0.3944(8) 0.066(3) Uani 1 1 d . . . . .
H23 H 1.3018 0.8224 0.4377 0.080 Uiso 1 1 calc R U . . .
C24 C 1.1946(12) 0.6754(11) 0.3891(8) 0.066(3) Uani 1 1 d . . . . .
H24 H 1.2473 0.6215 0.4287 0.079 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 1.504(7) . ?
P1 C4 1.777(10) . ?
P1 C14 1.796(10) . ?
O2 H2 0.8200 . ?
O2 C13 1.361(12) . ?
C3 C9 1.393(14) . ?
C3 C12 1.413(14) . ?
C3 C17 1.408(14) . ?
C4 C5 1.353(14) . ?
C4 C16 1.408(14) . ?
C5 H5 0.9300 . ?
C5 C12 1.455(14) . ?
C6 C10 1.521(14) . ?
C6 C11 1.390(15) . ?
C6 C13 1.390(14) . ?
C7 H7 0.9300 . ?
C7 C14 1.406(14) . ?
C7 C18 1.383(15) . ?
C8 H8 0.9300 . ?
C8 C10 1.370(15) . ?
C8 C19 1.430(18) . ?
C9 H9 0.9300 . ?
C9 C16 1.362(15) . ?
C10 C14 1.385(13) . ?
C11 H11 0.9300 . ?
C11 C23 1.382(16) . ?
C12 C20 1.409(15) . ?
C13 C15 1.376(14) . ?
C15 H15 0.9300 . ?
C15 C24 1.357(15) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C21 1.349(16) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(17) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C22 1.365(16) . ?
C21 H21 0.9300 . ?
C21 C22 1.397(17) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.379(17) . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C4 109.6(4) . . ?
O1 P1 C14 112.5(4) . . ?
C4 P1 C14 108.5(5) . . ?
C13 O2 H2 109.5 . . ?
C9 C3 C12 118.6(9) . . ?
C9 C3 C17 124.1(10) . . ?
C17 C3 C12 117.3(9) . . ?
C5 C4 P1 116.5(8) . . ?
C5 C4 C16 119.4(9) . . ?
C16 C4 P1 124.0(8) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C12 121.2(9) . . ?
C12 C5 H5 119.4 . . ?
C11 C6 C10 119.8(9) . . ?
C11 C6 C13 119.5(10) . . ?
C13 C6 C10 120.4(9) . . ?
C14 C7 H7 119.4 . . ?
C18 C7 H7 119.4 . . ?
C18 C7 C14 121.2(11) . . ?
C10 C8 H8 119.6 . . ?
C10 C8 C19 120.9(12) . . ?
C19 C8 H8 119.6 . . ?
C3 C9 H9 118.9 . . ?
C16 C9 C3 122.3(10) . . ?
C16 C9 H9 118.9 . . ?
C8 C10 C6 117.8(10) . . ?
C8 C10 C14 119.0(10) . . ?
C14 C10 C6 123.1(9) . . ?
C6 C11 H11 120.1 . . ?
C23 C11 C6 119.8(11) . . ?
C23 C11 H11 120.1 . . ?
C3 C12 C5 118.0(9) . . ?
C20 C12 C3 120.3(10) . . ?
C20 C12 C5 121.7(10) . . ?
O2 C13 C6 118.5(9) . . ?
O2 C13 C15 121.7(9) . . ?
C15 C13 C6 119.7(10) . . ?
C7 C14 P1 114.0(8) . . ?
C10 C14 P1 125.5(8) . . ?
C10 C14 C7 120.2(10) . . ?
C13 C15 H15 119.7 . . ?
C24 C15 C13 120.6(11) . . ?
C24 C15 H15 119.7 . . ?
C4 C16 H16 119.7 . . ?
C9 C16 C4 120.5(10) . . ?
C9 C16 H16 119.7 . . ?
C3 C17 H17 119.1 . . ?
C21 C17 C3 121.8(11) . . ?
C21 C17 H17 119.1 . . ?
C7 C18 H18 120.6 . . ?
C19 C18 C7 118.9(12) . . ?
C19 C18 H18 120.6 . . ?
C8 C19 H19 120.1 . . ?
C18 C19 C8 119.8(12) . . ?
C18 C19 H19 120.1 . . ?
C12 C20 H20 120.0 . . ?
C22 C20 C12 119.9(11) . . ?
C22 C20 H20 120.0 . . ?
C17 C21 H21 119.7 . . ?
C17 C21 C22 120.6(11) . . ?
C22 C21 H21 119.7 . . ?
C20 C22 C21 120.1(12) . . ?
C20 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C11 C23 H23 120.2 . . ?
C24 C23 C11 119.7(12) . . ?
C24 C23 H23 120.2 . . ?
C15 C24 C23 120.7(11) . . ?
C15 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?

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 C4 C5 C12 176.1(8) . . . . ?
P1 C4 C16 C9 -176.8(8) . . . . ?
O1 P1 C4 C5 -22.5(9) . . . . ?
O1 P1 C4 C16 153.8(9) . . . . ?
O1 P1 C14 C7 -58.4(9) . . . . ?
O1 P1 C14 C10 114.9(8) . . . . ?
O2 C13 C15 C24 177.6(11) . . . . ?
C3 C9 C16 C4 1.2(17) . . . . ?
C3 C12 C20 C22 -2.2(17) . . . . ?
C3 C17 C21 C22 -1.5(18) . . . . ?
C4 P1 C14 C7 63.1(9) . . . . ?
C4 P1 C14 C10 -123.7(9) . . . . ?
C4 C5 C12 C3 0.9(15) . . . . ?
C4 C5 C12 C20 -178.1(10) . . . . ?
C5 C4 C16 C9 -0.7(16) . . . . ?
C5 C12 C20 C22 176.8(11) . . . . ?
C6 C10 C14 P1 6.7(14) . . . . ?
C6 C10 C14 C7 179.6(9) . . . . ?
C6 C11 C23 C24 2.6(18) . . . . ?
C6 C13 C15 C24 -0.3(17) . . . . ?
C7 C18 C19 C8 0(2) . . . . ?
C8 C10 C14 P1 -172.1(9) . . . . ?
C8 C10 C14 C7 0.7(15) . . . . ?
C9 C3 C12 C5 -0.5(15) . . . . ?
C9 C3 C12 C20 178.6(10) . . . . ?
C9 C3 C17 C21 -176.5(11) . . . . ?
C10 C6 C11 C23 -176.7(10) . . . . ?
C10 C6 C13 O2 -2.4(16) . . . . ?
C10 C6 C13 C15 175.5(10) . . . . ?
C10 C8 C19 C18 1(2) . . . . ?
C11 C6 C10 C8 48.4(15) . . . . ?
C11 C6 C10 C14 -130.4(11) . . . . ?
C11 C6 C13 O2 -175.5(10) . . . . ?
C11 C6 C13 C15 2.4(17) . . . . ?
C11 C23 C24 C15 -0.5(19) . . . . ?
C12 C3 C9 C16 -0.5(16) . . . . ?
C12 C3 C17 C21 0.3(15) . . . . ?
C12 C20 C22 C21 1(2) . . . . ?
C13 C6 C10 C8 -124.7(12) . . . . ?
C13 C6 C10 C14 56.5(15) . . . . ?
C13 C6 C11 C23 -3.5(17) . . . . ?
C13 C15 C24 C23 -0.7(19) . . . . ?
C14 P1 C4 C5 -145.7(8) . . . . ?
C14 P1 C4 C16 30.5(10) . . . . ?
C14 C7 C18 C19 -0.5(18) . . . . ?
C16 C4 C5 C12 -0.3(15) . . . . ?
C17 C3 C9 C16 176.3(11) . . . . ?
C17 C3 C12 C5 -177.5(9) . . . . ?
C17 C3 C12 C20 1.5(15) . . . . ?
C17 C21 C22 C20 1(2) . . . . ?
C18 C7 C14 P1 173.7(9) . . . . ?
C18 C7 C14 C10 0.1(16) . . . . ?
C19 C8 C10 C6 179.9(11) . . . . ?
C19 C8 C10 C14 -1.2(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.605(14)
2 0.395(14)

####################################################################### 
# 
# 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_210427a
_database_code_depnum_ccdc_archive 'CCDC 2080531'
loop_
_audit_author_name
_audit_author_address
'Zhan-Cai Li'
;Liaocheng University
China
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-05-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 O3 P'
_chemical_formula_sum            'C20 H17 O3 P'
_chemical_formula_weight         336.30
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.2777(9)
_cell_length_b                   21.057(2)
_cell_length_c                   20.145(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.107(2)
_cell_angle_gamma                90
_cell_volume                     3497.4(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    993
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.799
_cell_measurement_theta_min      2.248
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.171
_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    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_unetI/netI     0.3626
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            6048
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.030
_diffrn_reflns_v_R_equivalents   ?
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.983
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1810
_reflns_number_total             6048
_reflns_special_details          
;
 _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         0.498
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6048
_refine_ls_number_restraints     1206
_refine_ls_R_factor_all          0.3667
_refine_ls_R_factor_gt           0.1688
_refine_ls_restrained_S_all      0.940
_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)+(0.1583P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3427
_refine_ls_wR_factor_ref         0.4229
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.577(10)
 0.423(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. 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
4.a Ternary CH refined with riding coordinates:
 C53(H53), C3(H3)
4.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C26(H26), C30(H30), C44(H44), C49(H49), C58(H58),
 C77(H77), C78(H78), C82(H82), C87(H87), C89(H89), C20(H20), C24(H24), C25(H25),
  C37(H37), C38(H38), C41(H41), C45(H45), C46(H46), C63(H63), C68(H68),
 C73(H73), C80(H80)
4.c Idealised Me refined as rotating group:
 C72(H72A,H72B,H72C), C35(H35A,H35B,H35C)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O14(H14)
;
_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 0.1565(4) 0.10117(17) 0.03143(15) 0.0519(9) Uani 1 1 d . U . . .
O1 O -0.0005(9) 0.0977(4) -0.0150(4) 0.057(2) Uani 1 1 d . U . . .
O2 O 0.1368(10) -0.0082(4) 0.1030(4) 0.063(2) Uani 1 1 d . U . . .
H2 H 0.0476 -0.0140 0.0829 0.095 Uiso 1 1 calc R U . . .
C10 C 0.1310(16) 0.1501(6) 0.1021(6) 0.0574(18) Uani 1 1 d . U . . .
C19 C 0.1669(16) 0.1793(6) 0.2236(6) 0.063(2) Uani 1 1 d . U . . .
H19 H 0.1996 0.1682 0.2674 0.076 Uiso 1 1 calc R U . . .
C23 C 0.7417(16) 0.0279(6) 0.1498(6) 0.060(2) Uani 1 1 d . U . . .
H23 H 0.8500 0.0261 0.1664 0.072 Uiso 1 1 calc R U . . .
C26 C 0.6963(15) 0.0686(6) 0.0986(6) 0.058(2) Uani 1 1 d . U . . .
H26 H 0.7723 0.0969 0.0844 0.070 Uiso 1 1 calc R U . . .
C27 C 0.4944(14) 0.1140(6) 0.0079(5) 0.0508(17) Uani 1 1 d . U . . .
C30 C 0.0368(16) 0.2545(6) 0.1449(6) 0.062(2) Uani 1 1 d . U . . .
H30 H -0.0161 0.2929 0.1363 0.075 Uiso 1 1 calc R U . . .
C44 C 0.6102(15) 0.1385(6) -0.0314(5) 0.054(2) Uani 1 1 d . U . . .
H44 H 0.7184 0.1275 -0.0214 0.065 Uiso 1 1 calc R U . . .
C49 C 0.0567(15) 0.2109(6) 0.0918(6) 0.0607(19) Uani 1 1 d . U . . .
H49 H 0.0196 0.2227 0.0486 0.073 Uiso 1 1 calc R U . . .
C51 C 0.5340(15) 0.0689(6) 0.0661(6) 0.0533(18) Uani 1 1 d . U . . .
C53 C 0.2415(14) 0.0238(6) 0.0600(6) 0.0532(19) Uani 1 1 d . U . . .
H53 H 0.2464 -0.0029 0.0204 0.064 Uiso 1 1 calc R U . . .
C58 C 0.1870(15) 0.1366(6) 0.1701(5) 0.0595(19) Uani 1 1 d . U . . .
H58 H 0.2389 0.0981 0.1797 0.071 Uiso 1 1 calc R U . . .
C60 C 0.3244(14) 0.1321(6) -0.0131(5) 0.0517(17) Uani 1 1 d . U . . .
O65 O 0.0904(11) 0.2768(4) 0.2664(4) 0.0684(19) Uani 1 1 d . U . . .
C70 C 0.0955(16) 0.2394(6) 0.2080(6) 0.060(2) Uani 1 1 d . U . . .
C72 C 0.0059(18) 0.3393(6) 0.2555(6) 0.077(3) Uani 1 1 d . U . . .
H72A H 0.0687 0.3664 0.2294 0.115 Uiso 1 1 calc R U . . .
H72B H -0.0062 0.3590 0.2977 0.115 Uiso 1 1 calc R U . . .
H72C H -0.0992 0.3325 0.2323 0.115 Uiso 1 1 calc R U . . .
C77 C 0.4623(15) -0.0115(6) 0.1472(6) 0.058(2) Uani 1 1 d . U . . .
H77 H 0.3863 -0.0386 0.1634 0.070 Uiso 1 1 calc R U . . .
C78 C 0.4125(14) 0.1960(6) -0.1061(6) 0.056(2) Uani 1 1 d . U . . .
H78 H 0.3881 0.2220 -0.1429 0.067 Uiso 1 1 calc R U . . .
C79 C 0.4149(15) 0.0278(6) 0.0945(6) 0.0550(18) Uani 1 1 d . U . . .
C82 C 0.6271(15) -0.0120(6) 0.1782(6) 0.057(2) Uani 1 1 d . U . . .
H82 H 0.6568 -0.0372 0.2152 0.068 Uiso 1 1 calc R U . . .
C87 C 0.5693(15) 0.1792(6) -0.0853(5) 0.054(2) Uani 1 1 d . U . . .
H87 H 0.6526 0.1956 -0.1082 0.065 Uiso 1 1 calc R U . . .
C89 C 0.2892(15) 0.1713(6) -0.0679(5) 0.054(2) Uani 1 1 d . U . . .
H89 H 0.1816 0.1819 -0.0802 0.064 Uiso 1 1 calc R U . . .
P2 P 0.3370(4) 0.40123(17) 0.02802(16) 0.0540(9) Uani 1 1 d . U . . .
C3 C 0.2740(14) 0.4786(6) 0.0608(6) 0.0563(19) Uani 1 1 d . U . . .
H3 H 0.2455 0.5064 0.0225 0.068 Uiso 1 1 calc R U . . .
C4 C 0.1275(16) 0.4744(6) 0.1002(6) 0.0603(18) Uani 1 1 d . U . . .
O13 O 0.4574(10) 0.4036(4) -0.0246(4) 0.062(2) Uani 1 1 d . U . . .
O14 O 0.4119(10) 0.5079(4) 0.1007(4) 0.068(2) Uani 1 1 d . U . . .
H14 H 0.4945 0.5036 0.0815 0.102 Uiso 1 1 calc R U . . .
C20 C -0.0136(16) 0.3079(6) -0.0943(6) 0.062(2) Uani 1 1 d . U . . .
H20 H -0.0153 0.2812 -0.1311 0.074 Uiso 1 1 calc R U . . .
C24 C 0.5311(16) 0.2505(6) 0.1361(6) 0.068(2) Uani 1 1 d . U . . .
H24 H 0.5703 0.2106 0.1261 0.082 Uiso 1 1 calc R U . . .
C25 C -0.1535(16) 0.3239(6) -0.0665(6) 0.062(2) Uani 1 1 d . U . . .
H25 H -0.2510 0.3074 -0.0856 0.075 Uiso 1 1 calc R U . . .
O31 O 0.6092(12) 0.2352(4) 0.2564(4) 0.078(2) Uani 1 1 d . U . . .
C35 C 0.6538(19) 0.1693(7) 0.2449(6) 0.084(3) Uani 1 1 d . U . . .
H35A H 0.5659 0.1482 0.2195 0.125 Uiso 1 1 calc R U . . .
H35B H 0.6762 0.1482 0.2870 0.125 Uiso 1 1 calc R U . . .
H35C H 0.7486 0.1682 0.2208 0.125 Uiso 1 1 calc R U . . .
C37 C 0.1121(16) 0.5163(6) 0.1522(6) 0.062(2) Uani 1 1 d . U . . .
H37 H 0.1979 0.5435 0.1648 0.074 Uiso 1 1 calc R U . . .
C38 C -0.0311(16) 0.5195(6) 0.1875(6) 0.066(2) Uani 1 1 d . U . . .
H38 H -0.0375 0.5483 0.2222 0.079 Uiso 1 1 calc R U . . .
C40 C 0.5411(17) 0.2692(6) 0.2018(6) 0.067(2) Uani 1 1 d . U . . .
C41 C -0.1582(16) 0.3638(6) -0.0110(6) 0.060(2) Uani 1 1 d . U . . .
H41 H -0.2567 0.3735 0.0055 0.072 Uiso 1 1 calc R U . . .
C45 C 0.4648(15) 0.2887(6) 0.0835(6) 0.0636(19) Uani 1 1 d . U . . .
H45 H 0.4560 0.2735 0.0400 0.076 Uiso 1 1 calc R U . . .
C46 C 0.4926(17) 0.3315(6) 0.2169(6) 0.068(2) Uani 1 1 d . U . . .
H46 H 0.5030 0.3461 0.2607 0.081 Uiso 1 1 calc R U . . .
C52 C -0.0092(15) 0.4348(6) 0.0765(6) 0.0574(18) Uani 1 1 d . U . . .
C54 C 0.1436(15) 0.3727(6) -0.0087(6) 0.0557(17) Uani 1 1 d . U . . .
C55 C -0.0109(15) 0.3893(6) 0.0202(6) 0.0574(17) Uani 1 1 d . U . . .
C56 C 0.4115(15) 0.3509(6) 0.0977(6) 0.0580(18) Uani 1 1 d . U . . .
C63 C 0.1336(16) 0.3337(6) -0.0645(6) 0.060(2) Uani 1 1 d . U . . .
H63 H 0.2290 0.3240 -0.0835 0.072 Uiso 1 1 calc R U . . .
C68 C 0.4283(16) 0.3715(6) 0.1648(6) 0.0644(19) Uani 1 1 d . U . . .
H68 H 0.3961 0.4124 0.1749 0.077 Uiso 1 1 calc R U . . .
C73 C -0.1496(16) 0.4377(6) 0.1152(6) 0.063(2) Uani 1 1 d . U . . .
H73 H -0.2363 0.4107 0.1033 0.076 Uiso 1 1 calc R U . . .
C80 C -0.1614(16) 0.4784(6) 0.1688(6) 0.066(2) Uani 1 1 d . U . . .
H80 H -0.2538 0.4785 0.1919 0.079 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 1.534(7) . ?
P1 C10 1.784(13) . ?
P1 C53 1.847(12) . ?
P1 C60 1.839(12) . ?
O2 H2 0.8200 . ?
O2 C53 1.445(13) . ?
C10 C49 1.428(16) . ?
C10 C58 1.435(14) . ?
C19 H19 0.9300 . ?
C19 C58 1.425(16) . ?
C19 C70 1.420(17) . ?
C23 H23 0.9300 . ?
C23 C26 1.369(15) . ?
C23 C82 1.424(16) . ?
C26 H26 0.9300 . ?
C26 C51 1.442(16) . ?
C27 C44 1.396(15) . ?
C27 C51 1.520(15) . ?
C27 C60 1.483(16) . ?
C30 H30 0.9300 . ?
C30 C49 1.431(15) . ?
C30 C70 1.357(16) . ?
C44 H44 0.9300 . ?
C44 C87 1.401(15) . ?
C49 H49 0.9300 . ?
C51 C79 1.466(16) . ?
C53 H53 0.9800 . ?
C53 C79 1.541(16) . ?
C58 H58 0.9300 . ?
C60 C89 1.390(15) . ?
O65 C70 1.420(14) . ?
O65 C72 1.496(14) . ?
C72 H72A 0.9600 . ?
C72 H72B 0.9600 . ?
C72 H72C 0.9600 . ?
C77 H77 0.9300 . ?
C77 C79 1.375(15) . ?
C77 C82 1.449(16) . ?
C78 H78 0.9300 . ?
C78 C87 1.374(15) . ?
C78 C89 1.430(15) . ?
C82 H82 0.9300 . ?
C87 H87 0.9300 . ?
C89 H89 0.9300 . ?
P2 C3 1.851(13) . ?
P2 O13 1.518(8) . ?
P2 C54 1.806(13) . ?
P2 C56 1.822(12) . ?
C3 H3 0.9800 . ?
C3 C4 1.510(17) . ?
C3 O14 1.472(13) . ?
C4 C37 1.384(16) . ?
C4 C52 1.452(17) . ?
O14 H14 0.8200 . ?
C20 H20 0.9300 . ?
C20 C25 1.373(17) . ?
C20 C63 1.417(16) . ?
C24 H24 0.9300 . ?
C24 C40 1.375(16) . ?
C24 C45 1.403(16) . ?
C25 H25 0.9300 . ?
C25 C41 1.401(16) . ?
O31 C35 1.460(15) . ?
O31 C40 1.389(14) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C37 H37 0.9300 . ?
C37 C38 1.437(17) . ?
C38 H38 0.9300 . ?
C38 C80 1.409(18) . ?
C40 C46 1.413(17) . ?
C41 H41 0.9300 . ?
C41 C55 1.425(16) . ?
C45 H45 0.9300 . ?
C45 C56 1.420(17) . ?
C46 H46 0.9300 . ?
C46 C68 1.412(16) . ?
C52 C55 1.484(16) . ?
C52 C73 1.457(16) . ?
C54 C55 1.493(17) . ?
C54 C63 1.388(16) . ?
C56 C68 1.413(15) . ?
C63 H63 0.9300 . ?
C68 H68 0.9300 . ?
C73 H73 0.9300 . ?
C73 C80 1.389(16) . ?
C80 H80 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C10 111.1(5) . . ?
O1 P1 C53 115.2(5) . . ?
O1 P1 C60 110.8(5) . . ?
C10 P1 C53 109.2(6) . . ?
C10 P1 C60 109.4(6) . . ?
C60 P1 C53 100.4(6) . . ?
C53 O2 H2 109.5 . . ?
C49 C10 P1 118.8(9) . . ?
C58 C10 P1 126.6(10) . . ?
C58 C10 C49 114.5(11) . . ?
C58 C19 H19 121.0 . . ?
C70 C19 H19 121.0 . . ?
C70 C19 C58 117.9(12) . . ?
C26 C23 H23 119.2 . . ?
C26 C23 C82 121.7(12) . . ?
C82 C23 H23 119.2 . . ?
C23 C26 H26 119.1 . . ?
C23 C26 C51 121.8(13) . . ?
C51 C26 H26 119.1 . . ?
C44 C27 C51 123.8(11) . . ?
C44 C27 C60 115.1(10) . . ?
C60 C27 C51 121.0(10) . . ?
C49 C30 H30 120.1 . . ?
C70 C30 H30 120.1 . . ?
C70 C30 C49 119.7(13) . . ?
C27 C44 H44 118.8 . . ?
C87 C44 C27 122.4(12) . . ?
C87 C44 H44 118.8 . . ?
C10 C49 C30 122.9(12) . . ?
C10 C49 H49 118.6 . . ?
C30 C49 H49 118.6 . . ?
C26 C51 C27 118.7(11) . . ?
C26 C51 C79 116.9(11) . . ?
C79 C51 C27 124.3(11) . . ?
P1 C53 H53 107.1 . . ?
O2 C53 P1 111.5(8) . . ?
O2 C53 H53 107.1 . . ?
O2 C53 C79 109.9(9) . . ?
C79 C53 P1 113.9(9) . . ?
C79 C53 H53 107.1 . . ?
C10 C58 C19 123.3(12) . . ?
C10 C58 H58 118.4 . . ?
C19 C58 H58 118.4 . . ?
C27 C60 P1 120.6(9) . . ?
C89 C60 P1 118.9(9) . . ?
C89 C60 C27 120.5(11) . . ?
C70 O65 C72 114.5(9) . . ?
C19 C70 O65 110.7(11) . . ?
C30 C70 C19 121.5(13) . . ?
C30 C70 O65 127.7(12) . . ?
O65 C72 H72A 109.5 . . ?
O65 C72 H72B 109.5 . . ?
O65 C72 H72C 109.5 . . ?
H72A C72 H72B 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C79 C77 H77 119.0 . . ?
C79 C77 C82 122.0(12) . . ?
C82 C77 H77 119.0 . . ?
C87 C78 H78 121.9 . . ?
C87 C78 C89 116.2(11) . . ?
C89 C78 H78 121.9 . . ?
C51 C79 C53 119.2(10) . . ?
C77 C79 C51 120.1(12) . . ?
C77 C79 C53 120.3(12) . . ?
C23 C82 C77 117.2(11) . . ?
C23 C82 H82 121.4 . . ?
C77 C82 H82 121.4 . . ?
C44 C87 C78 123.4(12) . . ?
C44 C87 H87 118.3 . . ?
C78 C87 H87 118.3 . . ?
C60 C89 C78 122.3(12) . . ?
C60 C89 H89 118.8 . . ?
C78 C89 H89 118.8 . . ?
O13 P2 C3 116.3(5) . . ?
O13 P2 C54 109.8(5) . . ?
O13 P2 C56 111.1(5) . . ?
C54 P2 C3 99.9(6) . . ?
C54 P2 C56 110.4(6) . . ?
C56 P2 C3 108.9(6) . . ?
P2 C3 H3 107.5 . . ?
C4 C3 P2 113.6(9) . . ?
C4 C3 H3 107.5 . . ?
O14 C3 P2 109.6(8) . . ?
O14 C3 H3 107.5 . . ?
O14 C3 C4 110.9(9) . . ?
C37 C4 C3 119.5(12) . . ?
C37 C4 C52 119.6(12) . . ?
C52 C4 C3 120.0(11) . . ?
C3 O14 H14 109.5 . . ?
C25 C20 H20 121.4 . . ?
C25 C20 C63 117.2(12) . . ?
C63 C20 H20 121.4 . . ?
C40 C24 H24 118.4 . . ?
C40 C24 C45 123.3(13) . . ?
C45 C24 H24 118.4 . . ?
C20 C25 H25 118.1 . . ?
C20 C25 C41 123.8(13) . . ?
C41 C25 H25 118.1 . . ?
C40 O31 C35 117.1(10) . . ?
O31 C35 H35A 109.5 . . ?
O31 C35 H35B 109.5 . . ?
O31 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C4 C37 H37 118.7 . . ?
C4 C37 C38 122.7(13) . . ?
C38 C37 H37 118.6 . . ?
C37 C38 H38 120.5 . . ?
C80 C38 C37 119.0(12) . . ?
C80 C38 H38 120.5 . . ?
C24 C40 O31 126.8(13) . . ?
C24 C40 C46 118.6(12) . . ?
C46 C40 O31 114.2(11) . . ?
C25 C41 H41 120.2 . . ?
C25 C41 C55 119.6(13) . . ?
C55 C41 H41 120.2 . . ?
C24 C45 H45 120.5 . . ?
C24 C45 C56 118.9(12) . . ?
C56 C45 H45 120.5 . . ?
C40 C46 H46 120.4 . . ?
C40 C46 C68 119.2(12) . . ?
C68 C46 H46 120.4 . . ?
C4 C52 C55 125.2(12) . . ?
C4 C52 C73 115.8(11) . . ?
C73 C52 C55 118.8(11) . . ?
C55 C54 P2 121.4(9) . . ?
C63 C54 P2 121.0(10) . . ?
C63 C54 C55 117.5(11) . . ?
C41 C55 C52 122.0(12) . . ?
C41 C55 C54 118.0(11) . . ?
C52 C55 C54 119.9(11) . . ?
C45 C56 P2 118.1(9) . . ?
C45 C56 C68 118.0(12) . . ?
C68 C56 P2 123.8(10) . . ?
C20 C63 H63 118.1 . . ?
C54 C63 C20 123.8(13) . . ?
C54 C63 H63 118.1 . . ?
C46 C68 H68 119.1 . . ?
C56 C68 C46 121.8(13) . . ?
C56 C68 H68 119.1 . . ?
C52 C73 H73 118.1 . . ?
C80 C73 C52 123.8(13) . . ?
C80 C73 H73 118.1 . . ?
C38 C80 H80 120.6 . . ?
C73 C80 C38 118.8(13) . . ?
C73 C80 H80 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C10 C49 C30 -177.5(10) . . . . ?
P1 C10 C58 C19 177.6(10) . . . . ?
P1 C53 C79 C51 -42.2(14) . . . . ?
P1 C53 C79 C77 144.4(11) . . . . ?
P1 C60 C89 C78 -178.4(9) . . . . ?
O1 P1 C10 C49 -47.8(12) . . . . ?
O1 P1 C10 C58 136.4(11) . . . . ?
O1 P1 C53 O2 -66.7(9) . . . . ?
O1 P1 C53 C79 168.3(8) . . . . ?
O1 P1 C60 C27 -152.2(9) . . . . ?
O1 P1 C60 C89 26.0(11) . . . . ?
O2 C53 C79 C51 -168.1(11) . . . . ?
O2 C53 C79 C77 18.4(16) . . . . ?
C10 P1 C53 O2 59.2(10) . . . . ?
C10 P1 C53 C79 -65.9(10) . . . . ?
C10 P1 C60 C27 84.9(11) . . . . ?
C10 P1 C60 C89 -96.9(10) . . . . ?
C23 C26 C51 C27 -177.8(11) . . . . ?
C23 C26 C51 C79 5.7(18) . . . . ?
C26 C23 C82 C77 5.0(19) . . . . ?
C26 C51 C79 C53 -177.3(11) . . . . ?
C26 C51 C79 C77 -3.8(18) . . . . ?
C27 C44 C87 C78 -3.1(19) . . . . ?
C27 C51 C79 C53 6.5(18) . . . . ?
C27 C51 C79 C77 180.0(11) . . . . ?
C27 C60 C89 C78 -0.2(19) . . . . ?
C44 C27 C51 C26 23.6(18) . . . . ?
C44 C27 C51 C79 -160.2(12) . . . . ?
C44 C27 C60 P1 177.6(9) . . . . ?
C44 C27 C60 C89 -0.6(17) . . . . ?
C49 C10 C58 C19 1.6(18) . . . . ?
C49 C30 C70 C19 -4(2) . . . . ?
C49 C30 C70 O65 178.5(12) . . . . ?
C51 C27 C44 C87 179.0(11) . . . . ?
C51 C27 C60 P1 0.7(16) . . . . ?
C51 C27 C60 C89 -177.5(11) . . . . ?
C53 P1 C10 C49 -176.0(10) . . . . ?
C53 P1 C10 C58 8.2(14) . . . . ?
C53 P1 C60 C27 -29.9(11) . . . . ?
C53 P1 C60 C89 148.3(10) . . . . ?
C58 C10 C49 C30 -1.1(19) . . . . ?
C58 C19 C70 C30 5(2) . . . . ?
C58 C19 C70 O65 -177.7(10) . . . . ?
C60 P1 C10 C49 75.0(11) . . . . ?
C60 P1 C10 C58 -100.9(12) . . . . ?
C60 P1 C53 O2 174.2(8) . . . . ?
C60 P1 C53 C79 49.1(9) . . . . ?
C60 C27 C44 C87 2.2(17) . . . . ?
C60 C27 C51 C26 -159.8(11) . . . . ?
C60 C27 C51 C79 16.3(18) . . . . ?
C70 C19 C58 C10 -3.4(19) . . . . ?
C70 C30 C49 C10 3(2) . . . . ?
C72 O65 C70 C19 -175.7(11) . . . . ?
C72 O65 C70 C30 1.6(19) . . . . ?
C79 C77 C82 C23 -3.1(19) . . . . ?
C82 C23 C26 C51 -6.5(19) . . . . ?
C82 C77 C79 C51 2.7(19) . . . . ?
C82 C77 C79 C53 176.1(11) . . . . ?
C87 C78 C89 C60 -0.4(18) . . . . ?
C89 C78 C87 C44 2.1(18) . . . . ?
P2 C3 C4 C37 148.8(10) . . . . ?
P2 C3 C4 C52 -42.3(15) . . . . ?
P2 C54 C55 C41 -178.8(9) . . . . ?
P2 C54 C55 C52 5.6(17) . . . . ?
P2 C54 C63 C20 177.7(10) . . . . ?
P2 C56 C68 C46 -177.5(10) . . . . ?
C3 P2 C54 C55 -32.0(11) . . . . ?
C3 P2 C54 C63 148.8(11) . . . . ?
C3 P2 C56 C45 179.4(10) . . . . ?
C3 P2 C56 C68 -4.5(13) . . . . ?
C3 C4 C37 C38 173.5(11) . . . . ?
C3 C4 C52 C55 9.4(19) . . . . ?
C3 C4 C52 C73 -175.4(11) . . . . ?
C4 C37 C38 C80 0(2) . . . . ?
C4 C52 C55 C41 -164.2(12) . . . . ?
C4 C52 C55 C54 11.2(19) . . . . ?
C4 C52 C73 C80 4.5(19) . . . . ?
O13 P2 C3 C4 166.6(8) . . . . ?
O13 P2 C3 O14 -68.8(9) . . . . ?
O13 P2 C54 C55 -154.7(10) . . . . ?
O13 P2 C54 C63 26.1(12) . . . . ?
O13 P2 C56 C45 -51.4(12) . . . . ?
O13 P2 C56 C68 124.8(11) . . . . ?
O14 C3 C4 C37 24.9(16) . . . . ?
O14 C3 C4 C52 -166.2(11) . . . . ?
C20 C25 C41 C55 -1(2) . . . . ?
C24 C40 C46 C68 3(2) . . . . ?
C24 C45 C56 P2 176.4(10) . . . . ?
C24 C45 C56 C68 0.1(19) . . . . ?
C25 C20 C63 C54 1.4(19) . . . . ?
C25 C41 C55 C52 176.2(12) . . . . ?
C25 C41 C55 C54 0.7(18) . . . . ?
O31 C40 C46 C68 177.2(12) . . . . ?
C35 O31 C40 C24 -10(2) . . . . ?
C35 O31 C40 C46 176.7(12) . . . . ?
C37 C4 C52 C55 178.2(12) . . . . ?
C37 C4 C52 C73 -6.6(18) . . . . ?
C37 C38 C80 C73 -2.3(19) . . . . ?
C40 C24 C45 C56 3(2) . . . . ?
C40 C46 C68 C56 0(2) . . . . ?
C45 C24 C40 O31 -177.8(13) . . . . ?
C45 C24 C40 C46 -5(2) . . . . ?
C45 C56 C68 C46 -1(2) . . . . ?
C52 C4 C37 C38 5(2) . . . . ?
C52 C73 C80 C38 0(2) . . . . ?
C54 P2 C3 C4 48.6(10) . . . . ?
C54 P2 C3 O14 173.2(8) . . . . ?
C54 P2 C56 C45 70.6(12) . . . . ?
C54 P2 C56 C68 -113.2(11) . . . . ?
C55 C52 C73 C80 -179.9(12) . . . . ?
C55 C54 C63 C20 -1.5(19) . . . . ?
C56 P2 C3 C4 -67.1(10) . . . . ?
C56 P2 C3 O14 57.5(9) . . . . ?
C56 P2 C54 C55 82.6(11) . . . . ?
C56 P2 C54 C63 -96.6(11) . . . . ?
C63 C20 C25 C41 0(2) . . . . ?
C63 C54 C55 C41 0.5(18) . . . . ?
C63 C54 C55 C52 -175.2(11) . . . . ?
C73 C52 C55 C41 20.7(18) . . . . ?
C73 C52 C55 C54 -163.9(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.577(10)
2 0.423(10)

####################################################################### 
# 
# 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_201217g
_database_code_depnum_ccdc_archive 'CCDC 2070977'
loop_
_audit_author_name
_audit_author_address
'Zhan-Cai Li'
;Liaocheng University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-03-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H17 O2 P'
_chemical_formula_sum            'C20 H17 O2 P'
_chemical_formula_weight         320.30
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   9.8615(8)
_cell_length_b                   14.7818(12)
_cell_length_c                   21.4475(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3126.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2592
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.552
_cell_measurement_theta_min      2.659
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14740
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         1.899
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 1.000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1798
_reflns_number_total             2751
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.042
_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)+(0.0846P)²+3.5979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1842
_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
 C6-C17
 1.395 with sigma of 0.002
 C8-C10
 1.395 with sigma of 0.002
 C19-C16
 1.395 with sigma of 0.002
 C8-C19
 1.395 with sigma of 0.002
 C3-C15
 1.395 with sigma of 0.002
 C16-C15
 1.395 with sigma of 0.002
 C3-C10
 1.395 with sigma of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
C1 C 1.2874(4) 0.1092(3) 0.3725(2) 0.0497(11) Uani 1 1 d . . . . .
H1A H 1.2653 0.1158 0.4158 0.075 Uiso 1 1 calc R U . . .
H1B H 1.2772 0.1664 0.3518 0.075 Uiso 1 1 calc R U . . .
H1C H 1.3795 0.0889 0.3685 0.075 Uiso 1 1 calc R U . . .
P1 P 0.99534(10) 0.17191(6) 0.33855(4) 0.0315(3) Uani 1 1 d . . . . .
O2 O 0.7216(3) 0.16397(17) 0.35420(12) 0.0361(7) Uani 1 1 d . . . . .
C3 C 0.8060(3) 0.0612(2) 0.43027(14) 0.0298(8) Uani 1 1 d D . . . .
O1 O 1.0798(3) 0.24211(19) 0.31034(13) 0.0477(8) Uani 1 1 d . . . . .
C5 C 0.9756(3) 0.1862(2) 0.42088(18) 0.0302(8) Uani 1 1 d . . . . .
C6 C 1.0610(3) 0.0603(2) 0.32679(15) 0.0300(8) Uani 1 1 d D . . . .
C7 C 0.8915(3) 0.1320(2) 0.45739(17) 0.0301(8) Uani 1 1 d . . . . .
C8 C 0.6424(4) 0.0133(2) 0.35249(17) 0.0416(10) Uani 1 1 d D . . . .
H8 H 0.5900 0.0268 0.3177 0.050 Uiso 1 1 calc R U . . .
C9 C 1.0515(4) 0.2524(3) 0.4493(2) 0.0412(10) Uani 1 1 d . . . . .
H9 H 1.1068 0.2892 0.4250 0.049 Uiso 1 1 calc R U . . .
C10 C 0.7248(3) 0.0791(2) 0.37884(14) 0.0315(9) Uani 1 1 d D . . . .
C11 C 1.1945(4) 0.0413(3) 0.34340(17) 0.0365(9) Uani 1 1 d . . . . .
C12 C 0.8230(4) 0.1801(3) 0.30940(18) 0.0403(10) Uani 1 1 d . . . . .
H12A H 0.8097 0.2402 0.2922 0.048 Uiso 1 1 calc R U . . .
H12B H 0.8119 0.1371 0.2756 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8906(4) 0.1451(3) 0.52145(18) 0.0437(10) Uani 1 1 d . . . . .
H13 H 0.8370 0.1083 0.5466 0.052 Uiso 1 1 calc R U . . .
C14 C 1.0351(5) -0.0924(3) 0.29041(19) 0.0469(11) Uani 1 1 d . . . . .
H14 H 0.9814 -0.1375 0.2730 0.056 Uiso 1 1 calc R U . . .
C15 C 0.8005(4) -0.0249(2) 0.45628(19) 0.0447(11) Uani 1 1 d D . . . .
H15 H 0.8526 -0.0382 0.4912 0.054 Uiso 1 1 calc R U . . .
C16 C 0.7178(4) -0.0911(3) 0.4305(2) 0.0591(13) Uani 1 1 d D . . . .
H16 H 0.7154 -0.1485 0.4483 0.071 Uiso 1 1 calc R U . . .
C17 C 0.9821(4) -0.0079(2) 0.30037(17) 0.0377(9) Uani 1 1 d D . . . .
H17 H 0.8927 0.0041 0.2894 0.045 Uiso 1 1 calc R U . . .
C18 C 1.2431(5) -0.0440(3) 0.33175(19) 0.0455(11) Uani 1 1 d . . . . .
H18 H 1.3326 -0.0570 0.3419 0.055 Uiso 1 1 calc R U . . .
C19 C 0.6387(4) -0.0727(2) 0.3784(2) 0.0548(13) Uani 1 1 d D . . . .
H19 H 0.5839 -0.1174 0.3612 0.066 Uiso 1 1 calc R U . . .
C20 C 1.1661(5) -0.1102(3) 0.3060(2) 0.0505(12) Uani 1 1 d . . . . .
H20 H 1.2026 -0.1674 0.2991 0.061 Uiso 1 1 calc R U . . .
C21 C 1.0475(4) 0.2653(3) 0.5120(2) 0.0528(12) Uani 1 1 d . . . . .
H21 H 1.0993 0.3107 0.5304 0.063 Uiso 1 1 calc R U . . .
C22 C 0.9674(5) 0.2113(3) 0.5478(2) 0.0526(12) Uani 1 1 d . . . . .
H22 H 0.9651 0.2197 0.5908 0.063 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C11 1.495(6) . ?
P1 O1 1.462(3) . ?
P1 C5 1.789(4) . ?
P1 C6 1.790(4) . ?
P1 C12 1.815(4) . ?
O2 C10 1.361(4) . ?
O2 C12 1.407(5) . ?
C3 C7 1.464(5) . ?
C3 C10 1.3890(19) . ?
C3 C15 1.3907(19) . ?
C5 C7 1.394(5) . ?
C5 C9 1.375(5) . ?
C6 C11 1.393(5) . ?
C6 C17 1.3935(19) . ?
C7 C13 1.388(5) . ?
C8 H8 0.9300 . ?
C8 C10 1.3873(19) . ?
C8 C19 1.389(2) . ?
C9 H9 0.9300 . ?
C9 C21 1.361(6) . ?
C11 C18 1.372(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C22 1.361(6) . ?
C14 H14 0.9300 . ?
C14 C17 1.371(5) . ?
C14 C20 1.361(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(2) . ?
C16 H16 0.9300 . ?
C16 C19 1.389(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C20 1.356(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.361(7) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C1 H1A 109.5 . . ?
C11 C1 H1B 109.5 . . ?
C11 C1 H1C 109.5 . . ?
O1 P1 C5 112.77(17) . . ?
O1 P1 C6 112.95(17) . . ?
O1 P1 C12 110.08(17) . . ?
C5 P1 C6 106.69(16) . . ?
C5 P1 C12 103.30(17) . . ?
C6 P1 C12 110.60(17) . . ?
C10 O2 C12 113.9(3) . . ?
C10 C3 C7 120.8(3) . . ?
C10 C3 C15 118.1(3) . . ?
C15 C3 C7 121.1(3) . . ?
C7 C5 P1 123.5(3) . . ?
C9 C5 P1 117.5(3) . . ?
C9 C5 C7 119.0(4) . . ?
C11 C6 P1 119.4(2) . . ?
C11 C6 C17 119.1(3) . . ?
C17 C6 P1 121.5(3) . . ?
C5 C7 C3 122.0(3) . . ?
C13 C7 C3 119.3(3) . . ?
C13 C7 C5 118.7(4) . . ?
C10 C8 H8 120.2 . . ?
C10 C8 C19 119.6(3) . . ?
C19 C8 H8 120.2 . . ?
C5 C9 H9 119.2 . . ?
C21 C9 C5 121.5(4) . . ?
C21 C9 H9 119.2 . . ?
O2 C10 C3 119.8(3) . . ?
O2 C10 C8 118.3(3) . . ?
C8 C10 C3 121.8(3) . . ?
C6 C11 C1 123.5(4) . . ?
C18 C11 C1 118.6(4) . . ?
C18 C11 C6 117.9(4) . . ?
P1 C12 H12A 108.6 . . ?
P1 C12 H12B 108.6 . . ?
O2 C12 P1 114.8(3) . . ?
O2 C12 H12A 108.6 . . ?
O2 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C7 C13 H13 119.7 . . ?
C22 C13 C7 120.6(4) . . ?
C22 C13 H13 119.7 . . ?
C17 C14 H14 120.0 . . ?
C20 C14 H14 120.0 . . ?
C20 C14 C17 120.0(4) . . ?
C3 C15 H15 119.7 . . ?
C16 C15 C3 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.6 . . ?
C19 C16 C15 120.8(4) . . ?
C19 C16 H16 119.6 . . ?
C6 C17 H17 119.7 . . ?
C14 C17 C6 120.7(4) . . ?
C14 C17 H17 119.7 . . ?
C11 C18 H18 118.6 . . ?
C20 C18 C11 122.9(4) . . ?
C20 C18 H18 118.6 . . ?
C8 C19 C16 119.2(4) . . ?
C8 C19 H19 120.4 . . ?
C16 C19 H19 120.4 . . ?
C14 C20 H20 120.3 . . ?
C18 C20 C14 119.4(4) . . ?
C18 C20 H20 120.3 . . ?
C9 C21 H21 120.2 . . ?
C9 C21 C22 119.5(4) . . ?
C22 C21 H21 120.2 . . ?
C13 C22 C21 120.7(4) . . ?
C13 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C11 C18 C20 179.4(4) . . . . ?
P1 C5 C7 C3 -3.3(5) . . . . ?
P1 C5 C7 C13 175.8(3) . . . . ?
P1 C5 C9 C21 -177.0(3) . . . . ?
P1 C6 C11 C1 1.6(5) . . . . ?
P1 C6 C11 C18 -177.8(3) . . . . ?
P1 C6 C17 C14 178.5(3) . . . . ?
C3 C7 C13 C22 -179.0(4) . . . . ?
C3 C15 C16 C19 -0.3(7) . . . . ?
O1 P1 C5 C7 175.0(3) . . . . ?
O1 P1 C5 C9 -7.3(3) . . . . ?
O1 P1 C6 C11 53.1(3) . . . . ?
O1 P1 C6 C17 -125.8(3) . . . . ?
O1 P1 C12 O2 -141.2(3) . . . . ?
C5 P1 C6 C11 -71.3(3) . . . . ?
C5 P1 C6 C17 109.7(3) . . . . ?
C5 P1 C12 O2 -20.5(3) . . . . ?
C5 C7 C13 C22 1.9(6) . . . . ?
C5 C9 C21 C22 0.4(6) . . . . ?
C6 P1 C5 C7 -60.5(3) . . . . ?
C6 P1 C5 C9 117.3(3) . . . . ?
C6 P1 C12 O2 93.3(3) . . . . ?
C6 C11 C18 C20 -1.2(6) . . . . ?
C7 C3 C10 O2 -1.7(5) . . . . ?
C7 C3 C10 C8 -179.7(3) . . . . ?
C7 C3 C15 C16 179.3(4) . . . . ?
C7 C5 C9 C21 0.8(6) . . . . ?
C7 C13 C22 C21 -0.7(6) . . . . ?
C9 C5 C7 C3 178.9(3) . . . . ?
C9 C5 C7 C13 -1.9(5) . . . . ?
C9 C21 C22 C13 -0.5(7) . . . . ?
C10 O2 C12 P1 -62.2(4) . . . . ?
C10 C3 C7 C5 -48.4(5) . . . . ?
C10 C3 C7 C13 132.5(4) . . . . ?
C10 C3 C15 C16 1.3(6) . . . . ?
C10 C8 C19 C16 0.0(6) . . . . ?
C11 C6 C17 C14 -0.4(6) . . . . ?
C11 C18 C20 C14 0.4(7) . . . . ?
C12 P1 C5 C7 56.2(3) . . . . ?
C12 P1 C5 C9 -126.1(3) . . . . ?
C12 P1 C6 C11 177.0(3) . . . . ?
C12 P1 C6 C17 -1.9(4) . . . . ?
C12 O2 C10 C3 87.3(4) . . . . ?
C12 O2 C10 C8 -94.6(4) . . . . ?
C15 C3 C7 C5 133.6(4) . . . . ?
C15 C3 C7 C13 -45.5(5) . . . . ?
C15 C3 C10 O2 176.3(3) . . . . ?
C15 C3 C10 C8 -1.6(5) . . . . ?
C15 C16 C19 C8 -0.4(7) . . . . ?
C17 C6 C11 C1 -179.5(4) . . . . ?
C17 C6 C11 C18 1.2(5) . . . . ?
C17 C14 C20 C18 0.4(6) . . . . ?
C19 C8 C10 O2 -177.0(4) . . . . ?
C19 C8 C10 C3 1.0(6) . . . . ?
C20 C14 C17 C6 -0.4(6) . . . . ?

_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_201103d
_database_code_depnum_ccdc_archive 'CCDC 2070973'
loop_
_audit_author_name
_audit_author_address
'Zhan-Cai Li'
;Liaocheng University
China
;
_audit_update_record             
;
2021-03-17 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-03-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 O3 P'
_chemical_formula_sum            'C20 H19 O3 P'
_chemical_formula_weight         338.32
_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                   9.0317(9)
_cell_length_b                   9.3941(9)
_cell_length_c                   11.3045(11)
_cell_angle_alpha                75.041(2)
_cell_angle_beta                 74.257(2)
_cell_angle_gamma                63.6620(10)
_cell_volume                     816.70(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1122
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.980
_cell_measurement_theta_min      0.978
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.184
_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    1.376
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.1566
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3867
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.451
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.965
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1540
_reflns_number_total             2791
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.485
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.1035
_refine_ls_restrained_S_all      1.149
_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)+(0.0723P)²+0.8884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2153
_refine_ls_wR_factor_ref         0.2317
_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.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_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 0.9313(2) 0.6875(2) 0.33138(17) 0.0273(5) Uani 1 1 d . . . . .
O1 O 0.9712(6) 0.5142(5) 0.3625(5) 0.0424(13) Uani 1 1 d . . . . .
O2 O 0.7931(6) 0.7463(5) 0.5687(4) 0.0480(15) Uani 1 1 d . . . . .
H2 H 0.8713 0.6576 0.5748 0.072 Uiso 1 1 calc R U . . .
O4 O 0.4778(6) 1.1164(5) 0.2699(5) 0.0436(14) Uani 1 1 d . . . . .
H4 H 0.3949 1.1716 0.3148 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7749(7) 0.9296(7) 0.1421(6) 0.0272(16) Uani 1 1 d . . . . .
C5 C 1.1098(8) 0.7302(7) 0.3151(6) 0.0325(17) Uani 1 1 d . . . . .
C6 C 0.8444(7) 0.7699(7) 0.1930(6) 0.0282(16) Uani 1 1 d . . . . .
C7 C 0.7593(8) 1.0610(7) 0.2001(6) 0.0291(16) Uani 1 1 d . . . . .
C8 C 0.6059(9) 1.1562(7) 0.2609(6) 0.0341(18) Uani 1 1 d . . . . .
C9 C 0.8506(8) 0.6575(8) 0.1317(7) 0.0367(18) Uani 1 1 d . . . . .
H9 H 0.8993 0.5488 0.1640 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7646(8) 0.7930(8) 0.4491(6) 0.0380(18) Uani 1 1 d . . . . .
H10A H 0.7414 0.9067 0.4256 0.046 Uiso 1 1 calc R U . . .
H10B H 0.6640 0.7806 0.4478 0.046 Uiso 1 1 calc R U . . .
C11 C 1.3819(9) 0.7093(8) 0.2202(7) 0.046(2) Uani 1 1 d . . . . .
H11 H 1.4771 0.6719 0.1599 0.056 Uiso 1 1 calc R U . . .
C12 C 0.7107(8) 0.9695(8) 0.0373(7) 0.042(2) Uani 1 1 d . . . . .
H12 H 0.6598 1.0777 0.0046 0.050 Uiso 1 1 calc R U . . .
C13 C 1.2497(9) 0.6718(7) 0.2281(6) 0.0324(17) Uani 1 1 d . . . . .
C14 C 0.8930(9) 1.0984(8) 0.1872(7) 0.042(2) Uani 1 1 d . . . . .
H14 H 0.9963 1.0390 0.1425 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7876(9) 0.7011(9) 0.0254(7) 0.045(2) Uani 1 1 d . . . . .
H15 H 0.7927 0.6233 -0.0143 0.055 Uiso 1 1 calc R U . . .
C16 C 0.5918(10) 1.2782(8) 0.3118(7) 0.044(2) Uani 1 1 d . . . . .
H16 H 0.4887 1.3393 0.3557 0.053 Uiso 1 1 calc R U . . .
C17 C 0.7179(9) 0.8575(10) -0.0215(7) 0.048(2) Uani 1 1 d . . . . .
H17 H 0.6747 0.8890 -0.0944 0.058 Uiso 1 1 calc R U . . .
C18 C 1.1099(9) 0.8193(8) 0.3951(7) 0.044(2) Uani 1 1 d . . . . .
H18 H 1.0166 0.8559 0.4570 0.053 Uiso 1 1 calc R U . . .
C19 C 0.7265(11) 1.3114(9) 0.2993(8) 0.054(2) Uani 1 1 d . . . . .
H19 H 0.7149 1.3972 0.3327 0.065 Uiso 1 1 calc R U . . .
C20 C 1.2421(11) 0.8539(9) 0.3851(9) 0.059(2) Uani 1 1 d . . . . .
H20 H 1.2394 0.9157 0.4387 0.070 Uiso 1 1 calc R U . . .
C24 C 1.2622(9) 0.5747(9) 0.1382(7) 0.053(2) Uani 1 1 d . . . . .
H24A H 1.2088 0.5020 0.1793 0.080 Uiso 1 1 calc R U . . .
H24B H 1.3783 0.5145 0.1068 0.080 Uiso 1 1 calc R U . . .
H24C H 1.2074 0.6449 0.0705 0.080 Uiso 1 1 calc R U . . .
C22 C 1.3783(11) 0.7992(9) 0.2976(9) 0.056(2) Uani 1 1 d . . . . .
H22 H 1.4702 0.8231 0.2902 0.067 Uiso 1 1 calc R U . . .
C23 C 0.8781(11) 1.2212(9) 0.2385(8) 0.057(2) Uani 1 1 d . . . . .
H23 H 0.9713 1.2428 0.2319 0.068 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 1.469(4) . ?
P1 C5 1.780(7) . ?
P1 C6 1.779(7) . ?
P1 C10 1.814(6) . ?
O2 H2 0.8200 . ?
O2 C10 1.368(8) . ?
O4 H4 0.8200 . ?
O4 C8 1.338(8) . ?
C4 C6 1.375(8) . ?
C4 C7 1.478(9) . ?
C4 C12 1.353(9) . ?
C5 C13 1.362(9) . ?
C5 C18 1.382(9) . ?
C6 C9 1.380(9) . ?
C7 C8 1.376(8) . ?
C7 C14 1.364(9) . ?
C8 C16 1.354(9) . ?
C9 H9 0.9300 . ?
C9 C15 1.358(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C13 1.362(9) . ?
C11 C22 1.350(10) . ?
C12 H12 0.9300 . ?
C12 C17 1.353(10) . ?
C13 C24 1.483(9) . ?
C14 H14 0.9300 . ?
C14 C23 1.360(10) . ?
C15 H15 0.9300 . ?
C15 C17 1.340(10) . ?
C16 H16 0.9300 . ?
C16 C19 1.349(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C20 1.340(10) . ?
C19 H19 0.9300 . ?
C19 C23 1.351(11) . ?
C20 H20 0.9300 . ?
C20 C22 1.341(11) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C5 112.2(3) . . ?
O1 P1 C6 110.2(3) . . ?
O1 P1 C10 110.3(3) . . ?
C5 P1 C10 109.6(3) . . ?
C6 P1 C5 110.3(3) . . ?
C6 P1 C10 103.9(3) . . ?
C10 O2 H2 109.5 . . ?
C8 O4 H4 109.5 . . ?
C6 C4 C7 123.0(6) . . ?
C12 C4 C6 118.7(6) . . ?
C12 C4 C7 118.2(6) . . ?
C13 C5 P1 121.3(5) . . ?
C13 C5 C18 118.9(7) . . ?
C18 C5 P1 119.7(5) . . ?
C4 C6 P1 127.3(5) . . ?
C4 C6 C9 118.1(6) . . ?
C9 C6 P1 114.6(5) . . ?
C8 C7 C4 120.5(6) . . ?
C14 C7 C4 121.1(6) . . ?
C14 C7 C8 118.2(6) . . ?
O4 C8 C7 116.2(6) . . ?
O4 C8 C16 123.5(6) . . ?
C16 C8 C7 120.2(7) . . ?
C6 C9 H9 119.1 . . ?
C15 C9 C6 121.8(7) . . ?
C15 C9 H9 119.1 . . ?
P1 C10 H10A 108.1 . . ?
P1 C10 H10B 108.1 . . ?
O2 C10 P1 116.8(4) . . ?
O2 C10 H10A 108.1 . . ?
O2 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C13 C11 H11 119.1 . . ?
C22 C11 H11 119.1 . . ?
C22 C11 C13 121.7(7) . . ?
C4 C12 H12 118.8 . . ?
C4 C12 C17 122.3(7) . . ?
C17 C12 H12 118.8 . . ?
C5 C13 C11 118.4(7) . . ?
C5 C13 C24 123.0(7) . . ?
C11 C13 C24 118.5(7) . . ?
C7 C14 H14 119.4 . . ?
C23 C14 C7 121.2(7) . . ?
C23 C14 H14 119.4 . . ?
C9 C15 H15 120.4 . . ?
C17 C15 C9 119.2(7) . . ?
C17 C15 H15 120.4 . . ?
C8 C16 H16 119.8 . . ?
C19 C16 C8 120.3(7) . . ?
C19 C16 H16 119.8 . . ?
C12 C17 H17 120.1 . . ?
C15 C17 C12 119.8(8) . . ?
C15 C17 H17 120.1 . . ?
C5 C18 H18 119.4 . . ?
C20 C18 C5 121.2(7) . . ?
C20 C18 H18 119.4 . . ?
C16 C19 H19 119.7 . . ?
C16 C19 C23 120.6(8) . . ?
C23 C19 H19 119.7 . . ?
C18 C20 H20 120.1 . . ?
C18 C20 C22 119.7(8) . . ?
C22 C20 H20 120.1 . . ?
C13 C24 H24A 109.5 . . ?
C13 C24 H24B 109.5 . . ?
C13 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C22 H22 120.0 . . ?
C20 C22 C11 119.9(8) . . ?
C20 C22 H22 120.0 . . ?
C14 C23 H23 120.3 . . ?
C19 C23 C14 119.3(8) . . ?
C19 C23 H23 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 C5 C13 C11 179.8(5) . . . . ?
P1 C5 C13 C24 2.3(9) . . . . ?
P1 C5 C18 C20 -179.8(6) . . . . ?
P1 C6 C9 C15 179.2(5) . . . . ?
O1 P1 C5 C13 60.3(6) . . . . ?
O1 P1 C5 C18 -117.2(6) . . . . ?
O1 P1 C6 C4 172.3(5) . . . . ?
O1 P1 C6 C9 -8.2(6) . . . . ?
O1 P1 C10 O2 58.0(7) . . . . ?
O4 C8 C16 C19 179.8(7) . . . . ?
C4 C6 C9 C15 -1.3(9) . . . . ?
C4 C7 C8 O4 3.8(9) . . . . ?
C4 C7 C8 C16 -178.8(6) . . . . ?
C4 C7 C14 C23 178.8(7) . . . . ?
C4 C12 C17 C15 1.4(11) . . . . ?
C5 P1 C6 C4 -63.3(6) . . . . ?
C5 P1 C6 C9 116.2(5) . . . . ?
C5 P1 C10 O2 -66.0(6) . . . . ?
C5 C18 C20 C22 -1.2(12) . . . . ?
C6 P1 C5 C13 -62.9(6) . . . . ?
C6 P1 C5 C18 119.5(6) . . . . ?
C6 P1 C10 O2 176.1(5) . . . . ?
C6 C4 C7 C8 -105.0(8) . . . . ?
C6 C4 C7 C14 79.8(8) . . . . ?
C6 C4 C12 C17 -2.5(10) . . . . ?
C6 C9 C15 C17 0.2(10) . . . . ?
C7 C4 C6 P1 -1.4(9) . . . . ?
C7 C4 C6 C9 179.2(6) . . . . ?
C7 C4 C12 C17 -179.4(6) . . . . ?
C7 C8 C16 C19 2.6(11) . . . . ?
C7 C14 C23 C19 -2.6(12) . . . . ?
C8 C7 C14 C23 3.5(11) . . . . ?
C8 C16 C19 C23 -1.7(12) . . . . ?
C9 C15 C17 C12 -0.2(11) . . . . ?
C10 P1 C5 C13 -176.7(5) . . . . ?
C10 P1 C5 C18 5.7(7) . . . . ?
C10 P1 C6 C4 54.1(6) . . . . ?
C10 P1 C6 C9 -126.4(5) . . . . ?
C12 C4 C6 P1 -178.2(5) . . . . ?
C12 C4 C6 C9 2.4(9) . . . . ?
C12 C4 C7 C8 71.8(8) . . . . ?
C12 C4 C7 C14 -103.4(8) . . . . ?
C13 C5 C18 C20 2.6(11) . . . . ?
C13 C11 C22 C20 0.1(12) . . . . ?
C14 C7 C8 O4 179.2(6) . . . . ?
C14 C7 C8 C16 -3.5(10) . . . . ?
C16 C19 C23 C14 1.6(13) . . . . ?
C18 C5 C13 C11 -2.6(10) . . . . ?
C18 C5 C13 C24 179.9(7) . . . . ?
C18 C20 C22 C11 -0.2(13) . . . . ?
C22 C11 C13 C5 1.3(10) . . . . ?
C22 C11 C13 C24 179.0(7) . . . . ?

_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_200801g
_database_code_depnum_ccdc_archive 'CCDC 2072520'
loop_
_audit_author_name
_audit_author_address
'Zhan-Cai Li'
;Liaocheng University
China
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_audit_creation_date             2021-03-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C23 H29 O2 P), C H Cl3'
_chemical_formula_sum            'C47 H57 Cl3 O4 P2'
_chemical_formula_weight         854.21
_chemical_absolute_configuration unk
_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'
Cl Cl 0.1484 0.1585 '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                   9.4585(8)
_cell_length_b                   15.8220(16)
_cell_length_c                   30.565(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4574.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3666
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.250
_cell_measurement_theta_min      2.377
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.311
_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    1.240
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.33
_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  0.0984
_diffrn_reflns_av_unetI/netI     0.1358
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23017
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.254
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.998
_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         0.776
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3464
_reflns_number_total             8026
_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         0.911
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.169
_refine_ls_abs_structure_details 
;
 Flack x determined using 1115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_coef       0.090(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         8026
_refine_ls_number_restraints     1488
_refine_ls_R_factor_all          0.2241
_refine_ls_R_factor_gt           0.1309
_refine_ls_restrained_S_all      1.091
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3201
_refine_ls_wR_factor_ref         0.3735
_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:
 C1(H1), C4(H4A), C6(H6), C9(H9), C18(H18), C23(H23), C24(H24), C33(H33),
 C38(H38), C42(H42), C52(H52)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B), C20(H20A,H20B), C35(H35A,
 H35B), C41(H41A,H41B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C17(H17), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30),
 C31(H31), C34(H34), C36(H36), C37(H37), C39(H39), C40(H40), C44(H44), C46(H46),
  C57(H57)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C32(H32A,H32B,H32C), C43(H43A,H43B,H43C), C45(H45A,H45B,
 H45C), C48(H48A,H48B,H48C), C56(H56A,H56B,H56C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_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 0.8440(5) 0.6457(2) 0.66992(12) 0.0682(11) Uani 1 1 d . U . . .
P2 P 0.5939(4) 0.4834(2) 0.55563(12) 0.0584(10) Uani 1 1 d . U . . .
C1 C 0.9550(17) 0.6394(9) 0.6218(5) 0.073(2) Uani 1 1 d . U . . .
H1 H 1.0083 0.5863 0.6214 0.087 Uiso 1 1 calc R U . . .
O1 O 0.7448(10) 0.5072(5) 0.5616(3) 0.068(2) Uani 1 1 d . U . . .
O2 O 0.4939(11) 0.5655(6) 0.6240(3) 0.069(2) Uani 1 1 d . U . . .
H2 H 0.5722 0.5733 0.6348 0.104 Uiso 1 1 calc R U . . .
C4 C 0.5838(16) 0.3802(8) 0.5325(4) 0.062(2) Uani 1 1 d . U . . .
H4A H 0.4876 0.3725 0.5213 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2765(16) 0.4983(8) 0.5578(5) 0.067(2) Uani 1 1 d . U . . .
C6 C 0.6159(16) 0.2241(8) 0.5542(5) 0.067(3) Uani 1 1 d . U . . .
H6 H 0.5234 0.2077 0.5425 0.080 Uiso 1 1 calc R U . . .
C7 C 0.3512(17) 0.5590(9) 0.5294(5) 0.068(2) Uani 1 1 d . U . . .
C8 C 0.4944(17) 0.5584(9) 0.5265(5) 0.067(2) Uani 1 1 d . U . . .
C9 C 0.4891(15) 0.4852(8) 0.6051(4) 0.063(2) Uani 1 1 d . U . . .
H9 H 0.5255 0.4433 0.6259 0.076 Uiso 1 1 calc R U . . .
C10 C 1.1005(18) 0.8608(10) 0.6290(5) 0.076(2) Uani 1 1 d . U . . .
H10 H 1.0722 0.9159 0.6350 0.092 Uiso 1 1 calc R U . . .
C11 C 0.3382(16) 0.4633(9) 0.5928(5) 0.067(2) Uani 1 1 d . U . . .
C12 C 0.7233(17) 0.2156(9) 0.5182(5) 0.072(3) Uani 1 1 d . U . . .
H12A H 0.7253 0.1577 0.5078 0.086 Uiso 1 1 calc R U . . .
H12B H 0.8164 0.2296 0.5293 0.086 Uiso 1 1 calc R U . . .
C13 C 0.7718(19) 0.7479(10) 0.6623(5) 0.076(2) Uani 1 1 d . U . . .
C14 C 1.0855(19) 0.5906(10) 0.7115(5) 0.081(2) Uani 1 1 d . U . . .
H14A H 1.0519 0.5329 0.7091 0.097 Uiso 1 1 calc R U . . .
H14B H 1.1348 0.6042 0.6846 0.097 Uiso 1 1 calc R U . . .
C15 C 0.8559(19) 0.8074(10) 0.6419(5) 0.076(2) Uani 1 1 d . U . . .
C16 C 0.6072(16) 0.3148(8) 0.5689(5) 0.065(2) Uani 1 1 d . U . . .
H16A H 0.6941 0.3288 0.5841 0.078 Uiso 1 1 calc R U . . .
H16B H 0.5305 0.3197 0.5898 0.078 Uiso 1 1 calc R U . . .
C17 C 0.1314(18) 0.3859(10) 0.6121(5) 0.077(3) Uani 1 1 d . U . . .
H17 H 0.0847 0.3473 0.6299 0.093 Uiso 1 1 calc R U . . .
C18 C 0.8868(19) 0.6306(11) 0.7603(5) 0.086(3) Uani 1 1 d . U . . .
H18 H 0.8527 0.5723 0.7582 0.104 Uiso 1 1 calc R U . . .
C19 C 1.0042(19) 0.7961(10) 0.6319(5) 0.076(2) Uani 1 1 d . U . . .
C20 C 0.6859(17) 0.2747(8) 0.4803(5) 0.068(3) Uani 1 1 d . U . . .
H20A H 0.7544 0.2677 0.4569 0.082 Uiso 1 1 calc R U . . .
H20B H 0.5936 0.2598 0.4688 0.082 Uiso 1 1 calc R U . . .
C21 C 1.0498(18) 0.7114(9) 0.6225(5) 0.072(2) Uani 1 1 d . U . . .
C22 C 0.2683(17) 0.4094(9) 0.6198(5) 0.073(3) Uani 1 1 d . U . . .
H22 H 0.3148 0.3879 0.6442 0.087 Uiso 1 1 calc R U . . .
C23 C 0.9574(18) 0.6491(10) 0.7157(5) 0.078(2) Uani 1 1 d . U . . .
H23 H 0.9944 0.7069 0.7174 0.093 Uiso 1 1 calc R U . . .
C24 C 0.6683(16) 0.4272(9) 0.4567(5) 0.067(3) Uani 1 1 d . U . . .
H24 H 0.6693 0.4845 0.4688 0.080 Uiso 1 1 calc R U . . .
O3 O 0.7349(11) 0.5786(6) 0.6728(3) 0.078(3) Uani 1 1 d . U . . .
C26 C 0.793(2) 0.4205(11) 0.4257(6) 0.096(5) Uani 1 1 d . U . . .
H26A H 0.8793 0.4168 0.4424 0.144 Uiso 1 1 calc R U . . .
H26B H 0.7967 0.4696 0.4073 0.144 Uiso 1 1 calc R U . . .
H26C H 0.7835 0.3708 0.4080 0.144 Uiso 1 1 calc R U . . .
C27 C 1.237(2) 0.8451(10) 0.6173(5) 0.084(3) Uani 1 1 d . U . . .
H27 H 1.2994 0.8906 0.6160 0.101 Uiso 1 1 calc R U . . .
C28 C 0.579(2) 0.8430(10) 0.6631(5) 0.086(3) Uani 1 1 d . U . . .
H28 H 0.4847 0.8530 0.6700 0.103 Uiso 1 1 calc R U . . .
C29 C 0.5638(18) 0.6213(8) 0.5024(5) 0.072(2) Uani 1 1 d . U . . .
H29 H 0.6618 0.6213 0.5001 0.087 Uiso 1 1 calc R U . . .
C30 C 0.0659(18) 0.4226(9) 0.5761(5) 0.077(3) Uani 1 1 d . U . . .
H30 H -0.0282 0.4094 0.5705 0.092 Uiso 1 1 calc R U . . .
C31 C 0.7973(19) 0.8884(10) 0.6344(5) 0.081(3) Uani 1 1 d . U . . .
H31 H 0.8521 0.9302 0.6213 0.097 Uiso 1 1 calc R U . . .
C32 C 0.528(2) 0.4168(11) 0.4320(6) 0.094(4) Uani 1 1 d . U . . .
H32A H 0.5066 0.4679 0.4164 0.141 Uiso 1 1 calc R U . . .
H32B H 0.4533 0.4053 0.4526 0.141 Uiso 1 1 calc R U . . .
H32C H 0.5352 0.3708 0.4117 0.141 Uiso 1 1 calc R U . . .
C33 C 0.6848(16) 0.3662(8) 0.4949(4) 0.062(2) Uani 1 1 d . U . . .
H33 H 0.7793 0.3769 0.5068 0.074 Uiso 1 1 calc R U . . .
C34 C 0.1328(16) 0.4761(9) 0.5492(5) 0.072(2) Uani 1 1 d . U . . .
H34 H 0.0860 0.4986 0.5251 0.087 Uiso 1 1 calc R U . . .
C35 C 1.121(2) 0.5791(12) 0.7897(5) 0.094(3) Uani 1 1 d . U . . .
H35A H 1.1886 0.5898 0.8130 0.112 Uiso 1 1 calc R U . . .
H35B H 1.0959 0.5198 0.7909 0.112 Uiso 1 1 calc R U . . .
C36 C 0.6348(19) 0.7653(10) 0.6701(5) 0.083(3) Uani 1 1 d . U . . .
H36 H 0.5766 0.7226 0.6807 0.099 Uiso 1 1 calc R U . . .
C37 C 0.348(2) 0.6818(10) 0.4827(5) 0.080(3) Uani 1 1 d . U . . .
H37 H 0.2970 0.7216 0.4668 0.096 Uiso 1 1 calc R U . . .
C38 C 1.189(2) 0.5953(11) 0.7488(5) 0.091(3) Uani 1 1 d . U . . .
H38 H 1.2248 0.6534 0.7498 0.109 Uiso 1 1 calc R U . . .
C39 C 0.2775(19) 0.6208(9) 0.5070(5) 0.075(3) Uani 1 1 d . U . . .
H39 H 0.1792 0.6215 0.5082 0.090 Uiso 1 1 calc R U . . .
C40 C 1.1944(18) 0.6997(10) 0.6108(5) 0.077(3) Uani 1 1 d . U . . .
H40 H 1.2265 0.6453 0.6051 0.093 Uiso 1 1 calc R U . . .
C41 C 0.994(2) 0.6298(11) 0.7976(5) 0.092(3) Uani 1 1 d . U . . .
H41A H 1.0231 0.6876 0.8035 0.110 Uiso 1 1 calc R U . . .
H41B H 0.9482 0.6086 0.8238 0.110 Uiso 1 1 calc R U . . .
C42 C 0.758(2) 0.6824(11) 0.7690(6) 0.090(3) Uani 1 1 d . U . . .
H42 H 0.6953 0.6758 0.7438 0.108 Uiso 1 1 calc R U . . .
C43 C 1.318(2) 0.5370(13) 0.7397(7) 0.119(6) Uani 1 1 d . U . . .
H43A H 1.3823 0.5398 0.7638 0.178 Uiso 1 1 calc R U . . .
H43B H 1.3645 0.5551 0.7134 0.178 Uiso 1 1 calc R U . . .
H43C H 1.2855 0.4798 0.7361 0.178 Uiso 1 1 calc R U . . .
C44 C 1.289(2) 0.7663(10) 0.6075(5) 0.084(3) Uani 1 1 d . U . . .
H44 H 1.3821 0.7580 0.5991 0.101 Uiso 1 1 calc R U . . .
C45 C 0.6492(19) 0.1670(8) 0.5931(5) 0.081(4) Uani 1 1 d . U . . .
H45A H 0.7354 0.1854 0.6067 0.122 Uiso 1 1 calc R U . . .
H45B H 0.6598 0.1098 0.5832 0.122 Uiso 1 1 calc R U . . .
H45C H 0.5734 0.1700 0.6139 0.122 Uiso 1 1 calc R U . . .
C46 C 0.658(2) 0.9062(11) 0.6463(6) 0.088(3) Uani 1 1 d . U . . .
H46 H 0.6210 0.9601 0.6428 0.105 Uiso 1 1 calc R U . . .
C48 C 0.677(3) 0.6608(15) 0.8079(7) 0.131(6) Uani 1 1 d . U . . .
H48A H 0.6842 0.6012 0.8132 0.196 Uiso 1 1 calc R U . . .
H48B H 0.5800 0.6759 0.8035 0.196 Uiso 1 1 calc R U . . .
H48C H 0.7141 0.6912 0.8326 0.196 Uiso 1 1 calc R U . . .
Cl3 Cl 0.1826(11) 0.8820(5) 0.7369(2) 0.177(3) Uani 1 1 d . U . . .
O4 O 0.8672(12) 0.6463(6) 0.5841(3) 0.078(3) Uani 1 1 d . U . . .
H4 H 0.8240 0.6019 0.5805 0.116 Uiso 1 1 calc R U . . .
Cl1 Cl 0.1914(12) 0.8516(8) 0.8258(3) 0.241(5) Uani 1 1 d . U . . .
Cl2 Cl 0.4305(10) 0.8653(8) 0.7837(4) 0.234(4) Uani 1 1 d . U . . .
C52 C 0.264(3) 0.903(2) 0.7847(8) 0.152(7) Uani 1 1 d . U . . .
H52 H 0.2648 0.9637 0.7905 0.183 Uiso 1 1 calc R U . . .
C56 C 0.789(2) 0.7753(13) 0.7738(7) 0.119(5) Uani 1 1 d . U . . .
H56A H 0.7016 0.8063 0.7737 0.179 Uiso 1 1 calc R U . . .
H56B H 0.8468 0.7938 0.7499 0.179 Uiso 1 1 calc R U . . .
H56C H 0.8376 0.7851 0.8009 0.179 Uiso 1 1 calc R U . . .
C57 C 0.485(2) 0.6828(10) 0.4824(5) 0.081(3) Uani 1 1 d . U . . .
H57 H 0.5312 0.7268 0.4682 0.097 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 C1 1.810(16) . ?
P1 C13 1.771(16) . ?
P1 C23 1.765(15) . ?
P1 O3 1.483(10) . ?
P2 O1 1.488(10) . ?
P2 C4 1.781(13) . ?
P2 C8 1.757(15) . ?
P2 C9 1.809(14) . ?
C1 H1 0.9800 . ?
C1 C21 1.45(2) . ?
C1 O4 1.424(16) . ?
O2 H2 0.8200 . ?
O2 C9 1.396(15) . ?
C4 H4A 0.9800 . ?
C4 C16 1.536(18) . ?
C4 C33 1.512(18) . ?
C5 C7 1.47(2) . ?
C5 C11 1.339(19) . ?
C5 C34 1.43(2) . ?
C6 H6 0.9800 . ?
C6 C12 1.505(19) . ?
C6 C16 1.505(18) . ?
C6 C45 1.525(19) . ?
C7 C8 1.36(2) . ?
C7 C39 1.38(2) . ?
C8 C29 1.400(19) . ?
C9 H9 0.9800 . ?
C9 C11 1.52(2) . ?
C10 H10 0.9300 . ?
C10 C19 1.37(2) . ?
C10 C27 1.36(2) . ?
C11 C22 1.36(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C20 1.530(18) . ?
C13 C15 1.38(2) . ?
C13 C36 1.35(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C23 1.53(2) . ?
C14 C38 1.50(2) . ?
C15 C19 1.45(2) . ?
C15 C31 1.42(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C22 1.37(2) . ?
C17 C30 1.39(2) . ?
C18 H18 0.9800 . ?
C18 C23 1.55(2) . ?
C18 C41 1.53(2) . ?
C18 C42 1.49(2) . ?
C19 C21 1.44(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C33 1.515(18) . ?
C21 C40 1.43(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9800 . ?
C24 H24 0.9800 . ?
C24 C26 1.52(2) . ?
C24 C32 1.54(2) . ?
C24 C33 1.524(19) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27 0.9300 . ?
C27 C44 1.37(2) . ?
C28 H28 0.9300 . ?
C28 C36 1.36(2) . ?
C28 C46 1.35(2) . ?
C29 H29 0.9300 . ?
C29 C57 1.37(2) . ?
C30 H30 0.9300 . ?
C30 C34 1.34(2) . ?
C31 H31 0.9300 . ?
C31 C46 1.39(2) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33 0.9800 . ?
C34 H34 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C38 1.43(2) . ?
C35 C41 1.46(2) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C37 C39 1.39(2) . ?
C37 C57 1.30(2) . ?
C38 H38 0.9800 . ?
C38 C43 1.55(3) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C40 C44 1.38(2) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42 0.9800 . ?
C42 C48 1.45(3) . ?
C42 C56 1.51(3) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44 0.9300 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 H46 0.9300 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
Cl3 C52 1.69(2) . ?
O4 H4 0.8200 . ?
Cl1 C52 1.64(3) . ?
Cl2 C52 1.68(3) . ?
C52 H52 0.9800 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 H57 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 P1 C1 99.6(7) . . ?
C23 P1 C1 107.1(7) . . ?
C23 P1 C13 108.1(7) . . ?
O3 P1 C1 114.4(7) . . ?
O3 P1 C13 113.1(8) . . ?
O3 P1 C23 113.4(7) . . ?
O1 P2 C4 109.4(6) . . ?
O1 P2 C8 113.9(7) . . ?
O1 P2 C9 114.8(6) . . ?
C4 P2 C9 108.5(6) . . ?
C8 P2 C4 112.9(7) . . ?
C8 P2 C9 96.9(7) . . ?
P1 C1 H1 110.8 . . ?
C21 C1 P1 107.7(10) . . ?
C21 C1 H1 110.8 . . ?
O4 C1 P1 108.4(11) . . ?
O4 C1 H1 110.8 . . ?
O4 C1 C21 108.2(12) . . ?
C9 O2 H2 109.5 . . ?
P2 C4 H4A 107.6 . . ?
C16 C4 P2 108.9(9) . . ?
C16 C4 H4A 107.6 . . ?
C33 C4 P2 113.7(9) . . ?
C33 C4 H4A 107.6 . . ?
C33 C4 C16 111.2(11) . . ?
C11 C5 C7 122.1(14) . . ?
C11 C5 C34 117.3(14) . . ?
C34 C5 C7 120.5(14) . . ?
C12 C6 H6 108.2 . . ?
C12 C6 C16 109.9(11) . . ?
C12 C6 C45 112.2(12) . . ?
C16 C6 H6 108.2 . . ?
C16 C6 C45 110.1(12) . . ?
C45 C6 H6 108.2 . . ?
C8 C7 C5 120.8(14) . . ?
C8 C7 C39 118.4(15) . . ?
C39 C7 C5 120.7(15) . . ?
C7 C8 P2 120.4(12) . . ?
C7 C8 C29 119.8(14) . . ?
C29 C8 P2 119.7(12) . . ?
P2 C9 H9 109.7 . . ?
O2 C9 P2 110.0(9) . . ?
O2 C9 H9 109.7 . . ?
O2 C9 C11 110.0(11) . . ?
C11 C9 P2 107.7(9) . . ?
C11 C9 H9 109.7 . . ?
C19 C10 H10 119.6 . . ?
C27 C10 H10 119.6 . . ?
C27 C10 C19 120.7(16) . . ?
C5 C11 C9 120.9(13) . . ?
C5 C11 C22 122.3(15) . . ?
C22 C11 C9 116.7(14) . . ?
C6 C12 H12A 109.6 . . ?
C6 C12 H12B 109.6 . . ?
C6 C12 C20 110.2(12) . . ?
H12A C12 H12B 108.1 . . ?
C20 C12 H12A 109.6 . . ?
C20 C12 H12B 109.6 . . ?
C15 C13 P1 117.4(14) . . ?
C36 C13 P1 122.3(13) . . ?
C36 C13 C15 119.7(16) . . ?
H14A C14 H14B 107.5 . . ?
C23 C14 H14A 108.5 . . ?
C23 C14 H14B 108.5 . . ?
C38 C14 H14A 108.5 . . ?
C38 C14 H14B 108.5 . . ?
C38 C14 C23 115.1(13) . . ?
C13 C15 C19 124.7(15) . . ?
C13 C15 C31 117.8(17) . . ?
C31 C15 C19 117.2(16) . . ?
C4 C16 H16A 108.3 . . ?
C4 C16 H16B 108.3 . . ?
C6 C16 C4 115.8(11) . . ?
C6 C16 H16A 108.3 . . ?
C6 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C22 C17 H17 121.7 . . ?
C22 C17 C30 116.5(16) . . ?
C30 C17 H17 121.7 . . ?
C23 C18 H18 105.2 . . ?
C41 C18 H18 105.2 . . ?
C41 C18 C23 111.8(15) . . ?
C42 C18 H18 105.2 . . ?
C42 C18 C23 113.9(14) . . ?
C42 C18 C41 114.5(14) . . ?
C10 C19 C15 124.4(15) . . ?
C10 C19 C21 118.8(16) . . ?
C15 C19 C21 116.7(15) . . ?
C12 C20 H20A 109.4 . . ?
C12 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C33 C20 C12 111.2(11) . . ?
C33 C20 H20A 109.4 . . ?
C33 C20 H20B 109.4 . . ?
C19 C21 C1 123.3(16) . . ?
C40 C21 C1 119.2(14) . . ?
C40 C21 C19 117.4(15) . . ?
C11 C22 C17 121.7(16) . . ?
C11 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
P1 C23 H23 106.6 . . ?
C14 C23 P1 113.3(10) . . ?
C14 C23 C18 107.5(13) . . ?
C14 C23 H23 106.6 . . ?
C18 C23 P1 115.5(12) . . ?
C18 C23 H23 106.6 . . ?
C26 C24 H24 107.1 . . ?
C26 C24 C32 111.2(13) . . ?
C32 C24 H24 107.1 . . ?
C33 C24 H24 107.1 . . ?
C33 C24 C26 110.7(13) . . ?
C33 C24 C32 113.4(12) . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C10 C27 H27 118.1 . . ?
C10 C27 C44 123.9(17) . . ?
C44 C27 H27 118.1 . . ?
C36 C28 H28 119.5 . . ?
C46 C28 H28 119.5 . . ?
C46 C28 C36 121.0(18) . . ?
C8 C29 H29 120.5 . . ?
C57 C29 C8 118.9(16) . . ?
C57 C29 H29 120.5 . . ?
C17 C30 H30 118.7 . . ?
C34 C30 C17 122.6(16) . . ?
C34 C30 H30 118.7 . . ?
C15 C31 H31 119.7 . . ?
C46 C31 C15 120.6(17) . . ?
C46 C31 H31 119.7 . . ?
C24 C32 H32A 109.5 . . ?
C24 C32 H32B 109.5 . . ?
C24 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C4 C33 H33 105.6 . . ?
C20 C33 C4 111.7(11) . . ?
C20 C33 C24 112.3(11) . . ?
C20 C33 H33 105.6 . . ?
C24 C33 C4 115.2(11) . . ?
C24 C33 H33 105.6 . . ?
C5 C34 H34 120.2 . . ?
C30 C34 C5 119.5(15) . . ?
C30 C34 H34 120.2 . . ?
H35A C35 H35B 107.6 . . ?
C38 C35 H35A 108.6 . . ?
C38 C35 H35B 108.6 . . ?
C38 C35 C41 114.6(15) . . ?
C41 C35 H35A 108.6 . . ?
C41 C35 H35B 108.6 . . ?
C13 C36 H36 118.9 . . ?
C28 C36 C13 122.2(17) . . ?
C28 C36 H36 118.9 . . ?
C39 C37 H37 120.3 . . ?
C57 C37 H37 120.3 . . ?
C57 C37 C39 119.4(17) . . ?
C14 C38 H38 107.1 . . ?
C14 C38 C43 110.3(15) . . ?
C35 C38 C14 111.2(17) . . ?
C35 C38 H38 107.1 . . ?
C35 C38 C43 113.7(15) . . ?
C43 C38 H38 107.1 . . ?
C7 C39 H39 119.5 . . ?
C37 C39 C7 121.0(17) . . ?
C37 C39 H39 119.5 . . ?
C21 C40 H40 118.8 . . ?
C44 C40 C21 122.5(15) . . ?
C44 C40 H40 118.8 . . ?
C18 C41 H41A 108.5 . . ?
C18 C41 H41B 108.5 . . ?
C35 C41 C18 115.2(14) . . ?
C35 C41 H41A 108.5 . . ?
C35 C41 H41B 108.5 . . ?
H41A C41 H41B 107.5 . . ?
C18 C42 H42 107.3 . . ?
C48 C42 C18 116.6(17) . . ?
C48 C42 H42 107.3 . . ?
C48 C42 C56 104.5(17) . . ?
C56 C42 C18 113.4(17) . . ?
C56 C42 H42 107.3 . . ?
C38 C43 H43A 109.5 . . ?
C38 C43 H43B 109.5 . . ?
C38 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C27 C44 C40 116.6(18) . . ?
C27 C44 H44 121.7 . . ?
C40 C44 H44 121.7 . . ?
C6 C45 H45A 109.5 . . ?
C6 C45 H45B 109.5 . . ?
C6 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C28 C46 C31 118.3(17) . . ?
C28 C46 H46 120.8 . . ?
C31 C46 H46 120.8 . . ?
C42 C48 H48A 109.5 . . ?
C42 C48 H48B 109.5 . . ?
C42 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C1 O4 H4 109.5 . . ?
Cl3 C52 H52 110.4 . . ?
Cl1 C52 Cl3 111.9(16) . . ?
Cl1 C52 Cl2 103.5(18) . . ?
Cl1 C52 H52 110.4 . . ?
Cl2 C52 Cl3 110.2(16) . . ?
Cl2 C52 H52 110.4 . . ?
C42 C56 H56A 109.5 . . ?
C42 C56 H56B 109.5 . . ?
C42 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C29 C57 H57 118.9 . . ?
C37 C57 C29 122.2(18) . . ?
C37 C57 H57 118.9 . . ?

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 C1 C21 C19 -45.8(17) . . . . ?
P1 C1 C21 C40 138.2(12) . . . . ?
P1 C13 C15 C19 -9(2) . . . . ?
P1 C13 C15 C31 177.9(11) . . . . ?
P1 C13 C36 C28 -178.2(12) . . . . ?
P2 C4 C16 C6 -174.4(10) . . . . ?
P2 C4 C33 C20 172.6(10) . . . . ?
P2 C4 C33 C24 -57.7(15) . . . . ?
P2 C8 C29 C57 -175.4(11) . . . . ?
P2 C9 C11 C5 -44.7(16) . . . . ?
P2 C9 C11 C22 137.6(12) . . . . ?
C1 P1 C13 C15 -32.4(13) . . . . ?
C1 P1 C13 C36 138.6(14) . . . . ?
C1 P1 C23 C14 -39.6(14) . . . . ?
C1 P1 C23 C18 -164.3(12) . . . . ?
C1 C21 C40 C44 175.1(14) . . . . ?
O1 P2 C4 C16 79.4(11) . . . . ?
O1 P2 C4 C33 -45.1(12) . . . . ?
O1 P2 C8 C7 -160.4(12) . . . . ?
O1 P2 C8 C29 15.4(14) . . . . ?
O1 P2 C9 O2 57.7(11) . . . . ?
O1 P2 C9 C11 177.5(9) . . . . ?
O2 C9 C11 C5 75.1(16) . . . . ?
O2 C9 C11 C22 -102.6(15) . . . . ?
C4 P2 C8 C7 74.0(14) . . . . ?
C4 P2 C8 C29 -110.1(12) . . . . ?
C4 P2 C9 O2 -179.6(9) . . . . ?
C4 P2 C9 C11 -59.8(11) . . . . ?
C5 C7 C8 P2 2(2) . . . . ?
C5 C7 C8 C29 -174.3(12) . . . . ?
C5 C7 C39 C37 175.3(14) . . . . ?
C5 C11 C22 C17 2(2) . . . . ?
C6 C12 C20 C33 60.5(17) . . . . ?
C7 C5 C11 C9 0(2) . . . . ?
C7 C5 C11 C22 177.9(14) . . . . ?
C7 C5 C34 C30 -178.2(13) . . . . ?
C7 C8 C29 C57 0(2) . . . . ?
C8 P2 C4 C16 -152.6(10) . . . . ?
C8 P2 C4 C33 82.8(12) . . . . ?
C8 P2 C9 O2 -62.6(10) . . . . ?
C8 P2 C9 C11 57.2(10) . . . . ?
C8 C7 C39 C37 -1(2) . . . . ?
C8 C29 C57 C37 -4(2) . . . . ?
C9 P2 C4 C16 -46.4(12) . . . . ?
C9 P2 C4 C33 -171.0(10) . . . . ?
C9 P2 C8 C7 -39.4(14) . . . . ?
C9 P2 C8 C29 136.4(12) . . . . ?
C9 C11 C22 C17 179.5(13) . . . . ?
C10 C19 C21 C1 -175.8(14) . . . . ?
C10 C19 C21 C40 0(2) . . . . ?
C10 C27 C44 C40 -1(2) . . . . ?
C11 C5 C7 C8 25(2) . . . . ?
C11 C5 C7 C39 -150.9(15) . . . . ?
C11 C5 C34 C30 0(2) . . . . ?
C12 C6 C16 C4 52.0(17) . . . . ?
C12 C20 C33 C4 -56.8(17) . . . . ?
C12 C20 C33 C24 172.0(12) . . . . ?
C13 P1 C1 C21 55.9(11) . . . . ?
C13 P1 C1 O4 -61.0(11) . . . . ?
C13 P1 C23 C14 -146.1(12) . . . . ?
C13 P1 C23 C18 89.3(13) . . . . ?
C13 C15 C19 C10 -151.9(15) . . . . ?
C13 C15 C19 C21 31(2) . . . . ?
C13 C15 C31 C46 -1(2) . . . . ?
C15 C13 C36 C28 -7(2) . . . . ?
C15 C19 C21 C1 1(2) . . . . ?
C15 C19 C21 C40 177.4(14) . . . . ?
C15 C31 C46 C28 -3(2) . . . . ?
C16 C4 C33 C20 49.3(16) . . . . ?
C16 C4 C33 C24 179.0(12) . . . . ?
C16 C6 C12 C20 -56.6(16) . . . . ?
C17 C30 C34 C5 -1(2) . . . . ?
C19 C10 C27 C44 1(3) . . . . ?
C19 C15 C31 C46 -175.1(15) . . . . ?
C19 C21 C40 C44 -1(2) . . . . ?
C21 C40 C44 C27 2(2) . . . . ?
C22 C17 C30 C34 2(2) . . . . ?
C23 P1 C1 C21 -56.6(12) . . . . ?
C23 P1 C1 O4 -173.4(9) . . . . ?
C23 P1 C13 C15 79.2(14) . . . . ?
C23 P1 C13 C36 -109.7(15) . . . . ?
C23 C14 C38 C35 56(2) . . . . ?
C23 C14 C38 C43 -177.0(15) . . . . ?
C23 C18 C41 C35 -49(2) . . . . ?
C23 C18 C42 C48 172.7(17) . . . . ?
C23 C18 C42 C56 -66(2) . . . . ?
O3 P1 C1 C21 176.8(10) . . . . ?
O3 P1 C1 O4 60.0(11) . . . . ?
O3 P1 C13 C15 -154.3(12) . . . . ?
O3 P1 C13 C36 16.8(16) . . . . ?
O3 P1 C23 C14 87.6(13) . . . . ?
O3 P1 C23 C18 -37.1(14) . . . . ?
C26 C24 C33 C4 167.4(13) . . . . ?
C26 C24 C33 C20 -63.2(17) . . . . ?
C27 C10 C19 C15 -176.9(15) . . . . ?
C27 C10 C19 C21 0(2) . . . . ?
C30 C17 C22 C11 -2(2) . . . . ?
C31 C15 C19 C10 21(2) . . . . ?
C31 C15 C19 C21 -155.6(13) . . . . ?
C32 C24 C33 C4 -66.8(16) . . . . ?
C32 C24 C33 C20 62.6(17) . . . . ?
C33 C4 C16 C6 -48.3(17) . . . . ?
C34 C5 C7 C8 -156.0(14) . . . . ?
C34 C5 C7 C39 28(2) . . . . ?
C34 C5 C11 C9 -178.3(12) . . . . ?
C34 C5 C11 C22 -1(2) . . . . ?
C36 C13 C15 C19 179.8(15) . . . . ?
C36 C13 C15 C31 7(2) . . . . ?
C36 C28 C46 C31 3(3) . . . . ?
C38 C14 C23 P1 176.7(12) . . . . ?
C38 C14 C23 C18 -54.4(19) . . . . ?
C38 C35 C41 C18 50(2) . . . . ?
C39 C7 C8 P2 178.0(11) . . . . ?
C39 C7 C8 C29 2(2) . . . . ?
C39 C37 C57 C29 6(3) . . . . ?
C41 C18 C23 P1 176.6(11) . . . . ?
C41 C18 C23 C14 48.9(18) . . . . ?
C41 C18 C42 C48 -57(2) . . . . ?
C41 C18 C42 C56 65(2) . . . . ?
C41 C35 C38 C14 -51(2) . . . . ?
C41 C35 C38 C43 -176.3(16) . . . . ?
C42 C18 C23 P1 -51.6(18) . . . . ?
C42 C18 C23 C14 -179.3(14) . . . . ?
C42 C18 C41 C35 179.9(15) . . . . ?
C45 C6 C12 C20 -179.4(12) . . . . ?
C45 C6 C16 C4 176.1(13) . . . . ?
C46 C28 C36 C13 2(3) . . . . ?
O4 C1 C21 C19 71.1(18) . . . . ?
O4 C1 C21 C40 -104.9(15) . . . . ?
C57 C37 C39 C7 -3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
