# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2445246'
loop_
_audit_author_name
_audit_author_address
'Zhaoqi Zhang'
;Ning bo university
China
;
_audit_update_record             
;
2025-04-28 deposited with the CCDC.	2025-07-04 downloaded from the CCDC.
;
_audit_creation_date             2025-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Cl O P'
_chemical_formula_sum            'C20 H16 Cl O P'
_chemical_formula_weight         338.75
_chemical_absolute_configuration ?
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   8.9934(2)
_cell_length_b                   9.8046(2)
_cell_length_c                   18.7482(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1653.15(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      5.09
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.802
_exptl_absorpt_coefficient_mu    2.960
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5152
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1355 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.6841.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16353
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.289
_diffrn_reflns_theta_min         5.090
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2915
_reflns_number_total             2952
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(5)
_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     208
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.1123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0734
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P001 P 0.50676(5) 0.61199(5) 0.20058(2) 0.01784(15) Uani 1 1 d . . . . .
Cl02 Cl 0.87740(6) 0.41714(7) 0.39955(3) 0.03753(19) Uani 1 1 d . . . . .
O003 O 0.57647(17) 0.47934(16) 0.18086(7) 0.0234(3) Uani 1 1 d . . . . .
C004 C 0.5564(2) 0.7479(2) 0.14002(10) 0.0211(4) Uani 1 1 d . . . . .
C005 C 0.5542(2) 0.6705(2) 0.28782(10) 0.0204(4) Uani 1 1 d . . . . .
H005 H 0.521720 0.757545 0.303782 0.025 Uiso 1 1 calc R . . . .
C006 C 0.6697(2) 0.6188(2) 0.40583(11) 0.0202(4) Uani 1 1 d . . . . .
C007 C 0.3054(2) 0.6018(2) 0.19943(10) 0.0204(4) Uani 1 1 d . . . . .
C008 C 0.6354(2) 0.5914(2) 0.33033(10) 0.0203(4) Uani 1 1 d . . . . .
H008 H 0.674711 0.510094 0.310237 0.024 Uiso 1 1 calc R . . . .
C009 C 0.4884(3) 0.7563(2) 0.07323(11) 0.0260(5) Uani 1 1 d . . . . .
H009 H 0.408623 0.696687 0.061775 0.031 Uiso 1 1 calc R . . . .
C00A C 0.6712(2) 0.8375(3) 0.15658(12) 0.0282(5) Uani 1 1 d . . . . .
H00A H 0.718147 0.832623 0.201913 0.034 Uiso 1 1 calc R . . . .
C00B C 0.6167(2) 0.7389(3) 0.51647(11) 0.0274(5) Uani 1 1 d . . . . .
H00B H 0.564377 0.808413 0.541275 0.033 Uiso 1 1 calc R . . . .
C00C C 0.5926(2) 0.7185(2) 0.44414(11) 0.0237(4) Uani 1 1 d . . . . .
H00C H 0.521856 0.773746 0.420056 0.028 Uiso 1 1 calc R . . . .
C00D C 0.2406(3) 0.4977(3) 0.16048(12) 0.0266(5) Uani 1 1 d . . . . .
H00D H 0.301535 0.435095 0.135153 0.032 Uiso 1 1 calc R . . . .
C00E C 0.5365(3) 0.8514(3) 0.02349(11) 0.0307(5) Uani 1 1 d . . . . .
H00E H 0.491091 0.855504 -0.022207 0.037 Uiso 1 1 calc R . . . .
C00F C 0.7968(3) 0.5582(3) 0.51614(12) 0.0295(5) Uani 1 1 d . . . . .
H00F H 0.866642 0.502634 0.540649 0.035 Uiso 1 1 calc R . . . .
C00G C 0.7730(2) 0.5407(2) 0.44332(12) 0.0250(5) Uani 1 1 d . . . . .
C00H C 0.6506(3) 0.9400(3) 0.04046(13) 0.0337(5) Uani 1 1 d . . . . .
H00H H 0.683324 1.005180 0.006428 0.040 Uiso 1 1 calc R . . . .
C00I C 0.2157(3) 0.6933(3) 0.23646(12) 0.0281(5) Uani 1 1 d . . . . .
H00I H 0.259087 0.765766 0.262897 0.034 Uiso 1 1 calc R . . . .
C00J C 0.7176(3) 0.9340(3) 0.10718(14) 0.0346(5) Uani 1 1 d . . . . .
H00J H 0.795051 0.995914 0.118977 0.042 Uiso 1 1 calc R . . . .
C00K C 0.0865(3) 0.4841(3) 0.15819(13) 0.0335(5) Uani 1 1 d . . . . .
H00K H 0.042661 0.413133 0.130822 0.040 Uiso 1 1 calc R . . . .
C00L C -0.0022(3) 0.5735(3) 0.19562(12) 0.0371(6) Uani 1 1 d . . . . .
H00L H -0.107214 0.563323 0.194722 0.044 Uiso 1 1 calc R . . . .
C00M C 0.7180(2) 0.6568(3) 0.55226(11) 0.0297(5) Uani 1 1 d . . . . .
H00M H 0.733109 0.668824 0.602021 0.036 Uiso 1 1 calc R . . . .
C00N C 0.0617(3) 0.6779(3) 0.23447(14) 0.0376(6) Uani 1 1 d . . . . .
H00N H 0.000202 0.739711 0.260013 0.045 Uiso 1 1 calc R . . . .


_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
P001 O003 1.4904(16) . ?
P001 C004 1.807(2) . ?
P001 C005 1.785(2) . ?
P001 C007 1.813(2) . ?
Cl02 C00G 1.739(2) . ?
C004 C009 1.396(3) . ?
C004 C00A 1.391(3) . ?
C005 C008 1.331(3) . ?
C006 C008 1.473(3) . ?
C006 C00C 1.397(3) . ?
C006 C00G 1.395(3) . ?
C007 C00D 1.384(3) . ?
C007 C00I 1.392(3) . ?
C009 C00E 1.388(3) . ?
C00A C00J 1.388(3) . ?
C00B C00C 1.388(3) . ?
C00B C00M 1.388(3) . ?
C00D C00K 1.392(3) . ?
C00E C00H 1.381(4) . ?
C00F C00G 1.392(3) . ?
C00F C00M 1.377(4) . ?
C00H C00J 1.390(4) . ?
C00I C00N 1.393(4) . ?
C00K C00L 1.378(4) . ?
C00L C00N 1.382(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O003 P001 C004 112.55(9) . . ?
O003 P001 C005 114.04(9) . . ?
O003 P001 C007 111.65(10) . . ?
C004 P001 C007 106.26(9) . . ?
C005 P001 C004 106.24(10) . . ?
C005 P001 C007 105.50(9) . . ?
C009 C004 P001 119.94(17) . . ?
C00A C004 P001 120.60(16) . . ?
C00A C004 C009 119.2(2) . . ?
C008 C005 P001 119.50(17) . . ?
C00C C006 C008 121.19(19) . . ?
C00G C006 C008 121.6(2) . . ?
C00G C006 C00C 117.11(19) . . ?
C00D C007 P001 117.88(17) . . ?
C00D C007 C00I 119.6(2) . . ?
C00I C007 P001 122.51(17) . . ?
C005 C008 C006 125.7(2) . . ?
C00E C009 C004 120.4(2) . . ?
C00J C00A C004 120.3(2) . . ?
C00C C00B C00M 119.4(2) . . ?
C00B C00C C006 121.7(2) . . ?
C007 C00D C00K 120.4(2) . . ?
C00H C00E C009 119.9(2) . . ?
C00M C00F C00G 119.3(2) . . ?
C006 C00G Cl02 120.31(17) . . ?
C00F C00G Cl02 117.76(18) . . ?
C00F C00G C006 121.9(2) . . ?
C00E C00H C00J 120.2(2) . . ?
C007 C00I C00N 119.5(2) . . ?
C00A C00J C00H 119.9(2) . . ?
C00L C00K C00D 120.0(2) . . ?
C00K C00L C00N 119.9(2) . . ?
C00F C00M C00B 120.46(19) . . ?
C00L C00N C00I 120.5(2) . . ?

_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_11
_database_code_depnum_ccdc_archive 'CCDC 2456178'
loop_
_audit_author_name
_audit_author_address
'Zhaoqi Zhang'
;Ning bo university
China
;
_audit_update_record             
;
2025-06-03 deposited with the CCDC.	2025-07-04 downloaded from the CCDC.
;
_audit_creation_date             2025-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 O P'
_chemical_formula_sum            'C20 H15 O P'
_chemical_formula_weight         302.29
_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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   11.7526(9)
_cell_length_b                   16.3049(15)
_cell_length_c                   16.4854(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3159.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6361
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      5.36
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    1.517
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6192
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1560 before and 0.0968 after correction.
The Ratio of minimum to maximum transmission is 0.8222.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.016
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.011
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1285
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            78595
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.350
_diffrn_reflns_theta_min         5.360
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2279
_reflns_number_total             2899
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.051
_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     199
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+1.6604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1120
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C1(H1), C9(H9), C4(H4), C16(H16), C8(H8), C11(H11), C3(H3),
 C20(H20), C2(H2), C10(H10), C19(H19), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.43482(4) 0.48823(3) 0.21050(3) 0.02421(16) Uani 1 1 d . . . . .
O1 O 0.55480(11) 0.47099(9) 0.18794(9) 0.0329(3) Uani 1 1 d . . . . .
C12 C 0.33663(16) 0.46485(12) 0.13029(11) 0.0248(4) Uani 1 1 d . . . . .
C14 C 0.35753(16) 0.39930(12) 0.35652(12) 0.0268(4) Uani 1 1 d . . . . .
C6 C 0.41231(16) 0.59351(12) 0.23980(11) 0.0245(4) Uani 1 1 d . . . . .
C15 C 0.32738(17) 0.35821(12) 0.43066(12) 0.0286(4) Uani 1 1 d . . . . .
C13 C 0.38527(17) 0.43323(12) 0.29519(12) 0.0278(4) Uani 1 1 d . . . . .
C5 C 0.31735(17) 0.61891(13) 0.28330(13) 0.0322(5) Uani 1 1 d . . . . .
H5 H 0.261298 0.580075 0.299075 0.039 Uiso 1 1 calc R . . . .
C7 C 0.38093(18) 0.44562(14) 0.05435(12) 0.0323(5) Uani 1 1 d . . . . .
H7 H 0.460961 0.442966 0.046709 0.039 Uiso 1 1 calc R . . . .
C1 C 0.49354(18) 0.65091(14) 0.21733(13) 0.0353(5) Uani 1 1 d . . . . .
H1 H 0.559461 0.633961 0.188501 0.042 Uiso 1 1 calc R . . . .
C9 C 0.19203(19) 0.43520(15) 0.00014(13) 0.0372(5) Uani 1 1 d . . . . .
H9 H 0.142534 0.425365 -0.044374 0.045 Uiso 1 1 calc R . . . .
C4 C 0.30435(19) 0.70093(14) 0.30372(14) 0.0380(5) Uani 1 1 d . . . . .
H4 H 0.239998 0.717918 0.334281 0.046 Uiso 1 1 calc R . . . .
C16 C 0.4100(2) 0.31619(14) 0.47484(13) 0.0375(5) Uani 1 1 d . . . . .
H16 H 0.486071 0.313169 0.455576 0.045 Uiso 1 1 calc R . . . .
C8 C 0.30826(19) 0.43033(15) -0.01016(13) 0.0387(5) Uani 1 1 d . . . . .
H8 H 0.338722 0.416424 -0.061741 0.046 Uiso 1 1 calc R . . . .
C11 C 0.21946(18) 0.46874(15) 0.14071(13) 0.0373(5) Uani 1 1 d . . . . .
H11 H 0.188463 0.481179 0.192484 0.045 Uiso 1 1 calc R . . . .
C3 C 0.38471(19) 0.75821(14) 0.27977(13) 0.0361(5) Uani 1 1 d . . . . .
H3 H 0.374939 0.814502 0.292884 0.043 Uiso 1 1 calc R . . . .
C20 C 0.21540(19) 0.36218(14) 0.45892(13) 0.0360(5) Uani 1 1 d . . . . .
H20 H 0.159152 0.390958 0.428874 0.043 Uiso 1 1 calc R . . . .
C2 C 0.4788(2) 0.73290(14) 0.23683(14) 0.0409(5) Uani 1 1 d . . . . .
H2 H 0.534143 0.771992 0.220415 0.049 Uiso 1 1 calc R . . . .
C10 C 0.14782(19) 0.45442(16) 0.07537(14) 0.0410(6) Uani 1 1 d . . . . .
H10 H 0.067742 0.457869 0.082429 0.049 Uiso 1 1 calc R . . . .
C19 C 0.1873(2) 0.32405(17) 0.53060(15) 0.0499(6) Uani 1 1 d . . . . .
H19 H 0.111209 0.326194 0.549869 0.060 Uiso 1 1 calc R . . . .
C17 C 0.3798(3) 0.27886(17) 0.54722(15) 0.0524(7) Uani 1 1 d . . . . .
H17 H 0.435608 0.250508 0.578025 0.063 Uiso 1 1 calc R . . . .
C18 C 0.2692(3) 0.28260(18) 0.57482(15) 0.0589(8) Uani 1 1 d . . . . .
H18 H 0.249101 0.256621 0.624374 0.071 Uiso 1 1 calc R . . . .


_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 1.4852(14) . ?
P1 C12 1.7960(19) . ?
P1 C6 1.803(2) . ?
P1 C13 1.759(2) . ?
C12 C7 1.392(3) . ?
C12 C11 1.389(3) . ?
C14 C15 1.438(3) . ?
C14 C13 1.198(3) . ?
C6 C5 1.390(3) . ?
C6 C1 1.387(3) . ?
C15 C16 1.394(3) . ?
C15 C20 1.398(3) . ?
C5 C4 1.388(3) . ?
C7 C8 1.387(3) . ?
C1 C2 1.386(3) . ?
C9 C8 1.379(3) . ?
C9 C10 1.381(3) . ?
C4 C3 1.386(3) . ?
C16 C17 1.386(3) . ?
C11 C10 1.387(3) . ?
C3 C2 1.376(3) . ?
C20 C19 1.375(3) . ?
C19 C18 1.383(4) . ?
C17 C18 1.378(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C12 112.67(9) . . ?
O1 P1 C6 112.75(9) . . ?
O1 P1 C13 114.63(9) . . ?
C12 P1 C6 107.77(9) . . ?
C13 P1 C12 105.28(9) . . ?
C13 P1 C6 102.96(9) . . ?
C7 C12 P1 118.02(15) . . ?
C11 C12 P1 122.43(15) . . ?
C11 C12 C7 119.49(18) . . ?
C13 C14 C15 178.5(2) . . ?
C5 C6 P1 122.67(15) . . ?
C1 C6 P1 118.03(15) . . ?
C1 C6 C5 119.30(19) . . ?
C16 C15 C14 120.10(19) . . ?
C16 C15 C20 120.3(2) . . ?
C20 C15 C14 119.59(19) . . ?
C14 C13 P1 174.78(19) . . ?
C4 C5 C6 120.06(19) . . ?
C8 C7 C12 120.01(19) . . ?
C2 C1 C6 120.2(2) . . ?
C8 C9 C10 119.8(2) . . ?
C3 C4 C5 120.4(2) . . ?
C17 C16 C15 119.1(2) . . ?
C9 C8 C7 120.4(2) . . ?
C10 C11 C12 119.87(19) . . ?
C2 C3 C4 119.5(2) . . ?
C19 C20 C15 119.4(2) . . ?
C3 C2 C1 120.6(2) . . ?
C9 C10 C11 120.5(2) . . ?
C20 C19 C18 120.5(2) . . ?
C18 C17 C16 120.4(2) . . ?
C17 C18 C19 120.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
