# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2299771'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2023-10-07 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2-hydroxy-4-methylbenzo[e][1,2]oxaphosphinine 2-oxide '
_chemical_name_common            ?
_chemical_melting_point          426
_chemical_formula_moiety         'C14 H10 Cl O3 P'
_chemical_formula_sum            'C14 H10 Cl O3 P'
_chemical_formula_weight         292.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.5378(3)
_cell_length_b                   10.6153(7)
_cell_length_c                   13.1018(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.716(3)
_cell_angle_gamma                90
_cell_volume                     630.83(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    164(2)
_cell_measurement_reflns_used    9447
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      34.16

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.429
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      164(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38061
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.470
_diffrn_reflns_theta_max         31.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4383
_reflns_number_gt                4325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2042 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4383
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.4576(2) 0.47622(11) 0.40925(9) 0.02092(18) Uani 1 1 d . . . . .
H3 H 0.459150 0.390122 0.429050 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5593(2) 0.51108(10) 0.31726(9) 0.01997(18) Uani 1 1 d . . . . .
C4A C 0.5594(2) 0.64423(11) 0.28501(9) 0.02093(18) Uani 1 1 d . . . . .
C5 C 0.7326(3) 0.68740(12) 0.20463(10) 0.0257(2) Uani 1 1 d . . . . .
H5 H 0.855122 0.629615 0.170307 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7274(3) 0.81258(12) 0.17478(11) 0.0297(2) Uani 1 1 d . . . . .
H6 H 0.846799 0.839691 0.120648 0.036 Uiso 1 1 calc R U . . .
C7 C 0.5490(3) 0.89872(13) 0.22335(12) 0.0308(3) Uani 1 1 d . . . . .
H7 H 0.543513 0.984063 0.201540 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3776(3) 0.85982(12) 0.30423(10) 0.0273(2) Uani 1 1 d . . . . .
H8 H 0.255089 0.918117 0.337976 0.033 Uiso 1 1 calc R U . . .
C8A C 0.3891(3) 0.73472(11) 0.33457(9) 0.02210(19) Uani 1 1 d . . . . .
C9 C 0.6730(3) 0.41288(10) 0.24747(9) 0.02083(18) Uani 1 1 d . . . . .
C10 C 0.8612(3) 0.31907(11) 0.28621(9) 0.0226(2) Uani 1 1 d . . . . .
H10 H 0.920416 0.320469 0.356365 0.027 Uiso 1 1 calc R U . . .
C11 C 0.9635(3) 0.22349(11) 0.22351(10) 0.0264(2) Uani 1 1 d . . . . .
H11 H 1.093353 0.160543 0.250089 0.032 Uiso 1 1 calc R U . . .
C12 C 0.8723(3) 0.22208(11) 0.12181(9) 0.0255(2) Uani 1 1 d . . . . .
C13 C 0.6846(3) 0.31314(13) 0.08105(10) 0.0290(2) Uani 1 1 d . . . . .
H13 H 0.624293 0.310330 0.011025 0.035 Uiso 1 1 calc R U . . .
C14 C 0.5856(3) 0.40883(13) 0.14402(10) 0.0276(2) Uani 1 1 d . . . . .
H14 H 0.457583 0.471957 0.116650 0.033 Uiso 1 1 calc R U . . .
Cl1 Cl 0.99929(10) 0.10262(3) 0.04309(2) 0.03899(10) Uani 1 1 d . . . . .
O1 O 0.2142(2) 0.70141(9) 0.41558(8) 0.02602(17) Uani 1 1 d . . . . .
O2 O 0.06529(18) 0.55313(11) 0.55171(8) 0.02711(18) Uani 1 1 d . . . . .
O3 O 0.57489(18) 0.64761(10) 0.55827(7) 0.02607(18) Uani 1 1 d . . . . .
H3A H 0.726006 0.602614 0.553150 0.039 Uiso 1 1 calc R U . . .
P2 P 0.32252(5) 0.59219(3) 0.49163(2) 0.01955(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 C4 1.3551(15) . ?
C3 P2 1.7594(11) . ?
C3 H3 0.9500 . ?
C4 C4A 1.4752(16) . ?
C4 C9 1.4889(15) . ?
C4A C8A 1.4043(15) . ?
C4A C5 1.4093(16) . ?
C5 C6 1.3852(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3954(19) . ?
C7 H7 0.9500 . ?
C8 C8A 1.3867(17) . ?
C8 H8 0.9500 . ?
C8A O1 1.3899(15) . ?
C9 C10 1.3975(16) . ?
C9 C14 1.4014(16) . ?
C10 C11 1.3937(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3835(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3848(19) . ?
C12 Cl1 1.7435(12) . ?
C13 C14 1.3917(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O1 P2 1.5966(10) . ?
O2 P2 1.4863(9) . ?
O3 P2 1.5363(9) . ?
O3 H3A 0.8400 . ?

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
C4 C3 P2 119.26(9) . . ?
C4 C3 H3 120.4 . . ?
P2 C3 H3 120.4 . . ?
C3 C4 C4A 121.29(10) . . ?
C3 C4 C9 119.24(10) . . ?
C4A C4 C9 119.46(9) . . ?
C8A C4A C5 116.75(11) . . ?
C8A C4A C4 121.20(10) . . ?
C5 C4A C4 122.04(10) . . ?
C6 C5 C4A 121.18(12) . . ?
C6 C5 H5 119.4 . . ?
C4A C5 H5 119.4 . . ?
C5 C6 C7 120.51(13) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 119.93(12) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C8A C8 C7 118.96(12) . . ?
C8A C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C8A O1 116.43(10) . . ?
C8 C8A C4A 122.61(11) . . ?
O1 C8A C4A 120.93(10) . . ?
C10 C9 C14 118.79(11) . . ?
C10 C9 C4 119.68(10) . . ?
C14 C9 C4 121.47(11) . . ?
C11 C10 C9 121.03(11) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 118.70(11) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 121.79(11) . . ?
C11 C12 Cl1 118.88(10) . . ?
C13 C12 Cl1 119.34(10) . . ?
C12 C13 C14 119.12(11) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C9 120.57(12) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C8A O1 P2 119.28(7) . . ?
P2 O3 H3A 109.5 . . ?
O2 P2 O3 112.93(6) . . ?
O2 P2 O1 107.52(5) . . ?
O3 P2 O1 106.68(6) . . ?
O2 P2 C3 115.04(6) . . ?
O3 P2 C3 110.43(5) . . ?
O1 P2 C3 103.40(5) . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2299776'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2023-10-07 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2-hydroxy-3,3-dimethyl-3H-benzo[d][1,2]oxaphosphole 2-oxide'
_chemical_name_common            ?
_chemical_melting_point          354
_chemical_formula_moiety         'C9 H11 O3 P, H2 O'
_chemical_formula_sum            'C9 H13 O4 P'
_chemical_formula_weight         216.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.4079(3)
_cell_length_b                   6.8535(3)
_cell_length_c                   22.6667(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     995.44(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9624
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      30.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.262
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5619
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24820
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.797
_diffrn_reflns_theta_max         30.265
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2970
_reflns_number_gt                2893
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.1021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2970
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.2226(2) 0.7660(2) 0.60783(6) 0.0137(3) Uani 1 1 d . . . . .
C3A C 0.2387(2) 0.7562(2) 0.67474(6) 0.0135(3) Uani 1 1 d . . . . .
C4 C 0.2295(2) 0.9105(2) 0.71412(7) 0.0188(3) Uani 1 1 d . . . . .
H4 H 0.215398 1.040709 0.700263 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2412(3) 0.8716(3) 0.77462(7) 0.0228(3) Uani 1 1 d . . . . .
H5 H 0.234139 0.976332 0.802023 0.027 Uiso 1 1 calc R U . . .
C6 C 0.2630(3) 0.6828(3) 0.79497(7) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.272166 0.659436 0.836197 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2716(2) 0.5260(3) 0.75594(6) 0.0200(3) Uani 1 1 d . . . . .
H7 H 0.286035 0.395761 0.769708 0.024 Uiso 1 1 calc R U . . .
C7A C 0.2584(2) 0.5674(2) 0.69646(6) 0.0146(3) Uani 1 1 d . . . . .
C8 C -0.0053(3) 0.7991(2) 0.58896(8) 0.0213(3) Uani 1 1 d . . . . .
H8A H -0.092831 0.694141 0.604760 0.032 Uiso 1 1 calc R U . . .
H8B H -0.014234 0.799506 0.545802 0.032 Uiso 1 1 calc R U . . .
H8C H -0.054033 0.924807 0.604306 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3660(3) 0.9212(2) 0.58096(7) 0.0232(3) Uani 1 1 d . . . . .
H9A H 0.322088 1.050806 0.594372 0.035 Uiso 1 1 calc R U . . .
H9B H 0.357667 0.914974 0.537832 0.035 Uiso 1 1 calc R U . . .
H9C H 0.510141 0.897179 0.593489 0.035 Uiso 1 1 calc R U . . .
O1 O 0.26327(18) 0.42070(17) 0.65361(5) 0.0171(2) Uani 1 1 d . . . . .
O2 O 0.17553(17) 0.41054(16) 0.54514(5) 0.0162(2) Uani 1 1 d . . . . .
O3 O 0.53676(17) 0.52239(17) 0.57745(5) 0.0192(2) Uani 1 1 d . . . . .
O4 O 0.78576(18) 0.26894(16) 0.55336(5) 0.0150(2) Uani 1 1 d . . . . .
P2 P 0.30397(5) 0.51801(5) 0.58956(2) 0.01169(10) Uani 1 1 d . . . . .
H41 H 0.903(4) 0.323(4) 0.5529(11) 0.032(6) Uiso 1 1 d . . . . .
H3 H 0.642(4) 0.410(4) 0.5656(13) 0.049(8) Uiso 1 1 d . . . . .
H42 H 0.766(4) 0.211(4) 0.5177(10) 0.031(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 C3A 1.5216(19) . ?
C3 C9 1.532(2) . ?
C3 C8 1.538(2) . ?
C3 P2 1.8256(14) . ?
C3A C4 1.385(2) . ?
C3A C7A 1.390(2) . ?
C4 C5 1.399(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 C7A 1.3804(19) . ?
C7 H7 0.9500 . ?
C7A O1 1.3984(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O1 P2 1.6188(11) . ?
O2 P2 1.4945(11) . ?
O3 P2 1.5170(11) . ?
O3 H3 1.06(3) . ?
O4 H41 0.84(3) . ?
O4 H3 1.36(3) . ?
O4 H42 0.91(2) . ?

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
C3A C3 C9 112.71(13) . . ?
C3A C3 C8 110.37(12) . . ?
C9 C3 C8 110.89(13) . . ?
C3A C3 P2 99.54(9) . . ?
C9 C3 P2 112.63(10) . . ?
C8 C3 P2 110.21(10) . . ?
C4 C3A C7A 119.11(14) . . ?
C4 C3A C3 127.28(14) . . ?
C7A C3A C3 113.58(12) . . ?
C3A C4 C5 118.94(15) . . ?
C3A C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.75(15) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 121.00(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C7A C7 C6 117.33(16) . . ?
C7A C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C7 C7A C3A 122.88(14) . . ?
C7 C7A O1 121.95(14) . . ?
C3A C7A O1 115.18(12) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7A O1 P2 109.28(9) . . ?
P2 O3 H3 130.9(16) . . ?
H41 O4 H3 107(2) . . ?
H41 O4 H42 108(2) . . ?
H3 O4 H42 113.4(19) . . ?
O2 P2 O3 115.43(6) . . ?
O2 P2 O1 108.21(7) . . ?
O3 P2 O1 109.20(6) . . ?
O2 P2 C3 117.03(7) . . ?
O3 P2 C3 107.67(7) . . ?
O1 P2 C3 97.70(6) . . ?

_refine_diff_density_max         0.787
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2299774'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2023-10-07 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2-(1-(2-hydroxyphenyl)-1-(4-methoxyphenyl)ethyl)-4-(4-methoxyphenyl)benzo[e][1,2]oxaphosphinine 2-oxide'
_chemical_name_common            ?
_chemical_melting_point          460
_chemical_formula_moiety         'C30 H27 O5 P'
_chemical_formula_sum            'C30 H27 O5 P'
_chemical_formula_weight         498.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4785(5)
_cell_length_b                   12.0901(6)
_cell_length_c                   12.1355(6)
_cell_angle_alpha                71.222(2)
_cell_angle_beta                 65.046(2)
_cell_angle_gamma                64.730(2)
_cell_volume                     1241.50(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9838
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      30.35

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59631
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.279
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7218
_reflns_number_gt                5282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.3169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7218
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.67324(17) 0.55740(13) 0.74649(14) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.574965 0.601354 0.742641 0.022 Uiso 1 1 calc R U . . .
C4 C 0.77311(16) 0.61694(13) 0.70303(13) 0.0174(3) Uani 1 1 d . . . . .
C4A C 0.93077(17) 0.54914(13) 0.69413(13) 0.0181(3) Uani 1 1 d . . . . .
C5 C 1.02735(17) 0.60831(14) 0.68044(14) 0.0207(3) Uani 1 1 d . . . . .
H5 H 0.992374 0.696193 0.671805 0.025 Uiso 1 1 calc R U . . .
C6 C 1.17239(18) 0.54119(15) 0.67929(14) 0.0232(3) Uani 1 1 d . . . . .
H6 H 1.235504 0.582937 0.671483 0.028 Uiso 1 1 calc R U . . .
C7 C 1.22645(18) 0.41276(15) 0.68949(15) 0.0257(3) Uani 1 1 d . . . . .
H7 H 1.326777 0.367058 0.687540 0.031 Uiso 1 1 calc R U . . .
C8 C 1.13451(18) 0.35150(14) 0.70248(15) 0.0239(3) Uani 1 1 d . . . . .
H8 H 1.171247 0.263804 0.708718 0.029 Uiso 1 1 calc R U . . .
C8A C 0.98849(17) 0.41925(14) 0.70628(14) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.65913(16) 0.30016(13) 0.77108(13) 0.0167(3) Uani 1 1 d . . . . .
C10 C 0.63407(18) 0.36578(14) 0.64584(14) 0.0205(3) Uani 1 1 d . . . . .
H10A H 0.727521 0.375724 0.583792 0.031 Uiso 1 1 calc R U . . .
H10B H 0.556293 0.447612 0.654552 0.031 Uiso 1 1 calc R U . . .
H10C H 0.602501 0.315600 0.619790 0.031 Uiso 1 1 calc R U . . .
C11 C 0.51138(17) 0.28511(13) 0.86688(13) 0.0175(3) Uani 1 1 d . . . . .
C12 C 0.39679(17) 0.38432(13) 0.92240(14) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.25844(18) 0.37575(14) 1.00147(14) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.181902 0.444992 1.037580 0.027 Uiso 1 1 calc R U . . .
C14 C 0.23289(19) 0.26515(15) 1.02732(15) 0.0250(3) Uani 1 1 d . . . . .
H14 H 0.139247 0.257698 1.082680 0.030 Uiso 1 1 calc R U . . .
C15 C 0.34443(19) 0.16539(15) 0.97213(15) 0.0252(3) Uani 1 1 d . . . . .
H15 H 0.326450 0.090016 0.988833 0.030 Uiso 1 1 calc R U . . .
C16 C 0.48176(18) 0.17525(14) 0.89287(14) 0.0207(3) Uani 1 1 d . . . . .
H16 H 0.557137 0.106360 0.855494 0.025 Uiso 1 1 calc R U . . .
C17 C 0.78131(17) 0.17212(13) 0.76539(14) 0.0178(3) Uani 1 1 d . . . . .
C18 C 0.83960(18) 0.11155(14) 0.66590(14) 0.0219(3) Uani 1 1 d . . . . .
H18 H 0.807836 0.152471 0.596009 0.026 Uiso 1 1 calc R U . . .
C19 C 0.94326(18) -0.00750(15) 0.66712(15) 0.0245(3) Uani 1 1 d . . . . .
H19 H 0.978908 -0.048434 0.599516 0.029 Uiso 1 1 calc R U . . .
C20 C 0.99524(17) -0.06725(13) 0.76546(15) 0.0217(3) Uani 1 1 d . . . . .
C21 C 0.93781(18) -0.00917(14) 0.86665(15) 0.0225(3) Uani 1 1 d . . . . .
H21 H 0.971838 -0.049667 0.935430 0.027 Uiso 1 1 calc R U . . .
C22 C 0.83037(18) 0.10842(13) 0.86616(14) 0.0211(3) Uani 1 1 d . . . . .
H22 H 0.789041 0.146631 0.936586 0.025 Uiso 1 1 calc R U . . .
C23 C 1.1666(2) -0.24141(17) 0.85065(19) 0.0369(4) Uani 1 1 d . . . . .
H23A H 1.213813 -0.188533 0.854190 0.055 Uiso 1 1 calc R U . . .
H23B H 1.242450 -0.322083 0.832415 0.055 Uiso 1 1 calc R U . . .
H23C H 1.089410 -0.253525 0.930280 0.055 Uiso 1 1 calc R U . . .
C24 C 0.71582(17) 0.75536(13) 0.67059(14) 0.0188(3) Uani 1 1 d . . . . .
C25 C 0.77680(18) 0.81907(14) 0.55531(15) 0.0213(3) Uani 1 1 d . . . . .
H25 H 0.864401 0.774932 0.497201 0.026 Uiso 1 1 calc R U . . .
C26 C 0.71101(18) 0.94701(14) 0.52384(15) 0.0228(3) Uani 1 1 d . . . . .
H26 H 0.752460 0.989292 0.444122 0.027 Uiso 1 1 calc R U . . .
C27 C 0.58495(18) 1.01238(13) 0.60918(15) 0.0215(3) Uani 1 1 d . . . . .
C28 C 0.52508(18) 0.95000(14) 0.72589(15) 0.0221(3) Uani 1 1 d . . . . .
H28 H 0.439881 0.994733 0.785096 0.027 Uiso 1 1 calc R U . . .
C29 C 0.58963(18) 0.82283(13) 0.75570(14) 0.0210(3) Uani 1 1 d . . . . .
H29 H 0.547482 0.780747 0.835292 0.025 Uiso 1 1 calc R U . . .
C30 C 0.5560(2) 1.20273(15) 0.46540(16) 0.0298(4) Uani 1 1 d . . . . .
H30A H 0.658626 1.200617 0.441894 0.045 Uiso 1 1 calc R U . . .
H30B H 0.488509 1.289169 0.460573 0.045 Uiso 1 1 calc R U . . .
H30C H 0.551323 1.162949 0.409114 0.045 Uiso 1 1 calc R U . . .
O1 O 0.89928(12) 0.35273(9) 0.72318(10) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.71420(12) 0.36918(9) 0.94215(10) 0.0220(2) Uani 1 1 d . . . . .
O12 O 0.42695(13) 0.49144(10) 0.89203(11) 0.0221(2) Uani 1 1 d . . . . .
O20 O 1.09995(14) -0.18326(10) 0.75600(11) 0.0300(3) Uani 1 1 d . . . . .
O27 O 0.51174(13) 1.13782(10) 0.58870(11) 0.0272(3) Uani 1 1 d . . . . .
P2 P 0.72572(4) 0.39709(3) 0.81075(4) 0.01730(10) Uani 1 1 d . . . . .
H12 H 0.370(3) 0.538(2) 0.952(2) 0.056(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 C4 1.3508(19) . ?
C3 P2 1.7736(15) . ?
C3 H3 0.9500 . ?
C4 C4A 1.471(2) . ?
C4 C24 1.4944(19) . ?
C4A C5 1.4011(19) . ?
C4A C8A 1.403(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 C8A 1.382(2) . ?
C8 H8 0.9500 . ?
C8A O1 1.3917(16) . ?
C9 C17 1.530(2) . ?
C9 C11 1.539(2) . ?
C9 C10 1.546(2) . ?
C9 P2 1.8538(13) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.394(2) . ?
C11 C16 1.3999(19) . ?
C12 O12 1.3626(17) . ?
C12 C13 1.387(2) . ?
C13 C14 1.387(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.390(2) . ?
C17 C22 1.392(2) . ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C20 O20 1.3667(18) . ?
C20 C21 1.391(2) . ?
C21 C22 1.387(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 O20 1.428(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.390(2) . ?
C24 C29 1.396(2) . ?
C25 C26 1.395(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(2) . ?
C26 H26 0.9500 . ?
C27 O27 1.3694(18) . ?
C27 C28 1.391(2) . ?
C28 C29 1.383(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 O27 1.428(2) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O1 P2 1.6211(11) . ?
O2 P2 1.4823(11) . ?
O12 H12 0.90(2) . ?

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
C4 C3 P2 119.96(12) . . ?
C4 C3 H3 120.0 . . ?
P2 C3 H3 120.0 . . ?
C3 C4 C4A 121.43(13) . . ?
C3 C4 C24 117.49(13) . . ?
C4A C4 C24 121.00(12) . . ?
C5 C4A C8A 116.95(14) . . ?
C5 C4A C4 122.62(13) . . ?
C8A C4A C4 120.34(12) . . ?
C6 C5 C4A 121.18(14) . . ?
C6 C5 H5 119.4 . . ?
C4A C5 H5 119.4 . . ?
C5 C6 C7 120.25(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.09(15) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8A C8 C7 119.22(14) . . ?
C8A C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C8A O1 116.94(13) . . ?
C8 C8A C4A 122.29(13) . . ?
O1 C8A C4A 120.77(13) . . ?
C17 C9 C11 108.81(11) . . ?
C17 C9 C10 113.03(12) . . ?
C11 C9 C10 108.60(11) . . ?
C17 C9 P2 106.40(9) . . ?
C11 C9 P2 113.21(9) . . ?
C10 C9 P2 106.86(9) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 117.49(14) . . ?
C12 C11 C9 121.02(12) . . ?
C16 C11 C9 121.24(13) . . ?
O12 C12 C13 121.80(14) . . ?
O12 C12 C11 116.21(13) . . ?
C13 C12 C11 121.97(13) . . ?
C12 C13 C14 119.38(14) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 119.83(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.27(14) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 121.05(14) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C18 C17 C22 117.57(14) . . ?
C18 C17 C9 122.50(13) . . ?
C22 C17 C9 119.78(13) . . ?
C19 C18 C17 121.00(14) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.66(14) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O20 C20 C19 115.91(13) . . ?
O20 C20 C21 124.62(14) . . ?
C19 C20 C21 119.46(14) . . ?
C22 C21 C20 119.33(14) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C17 121.89(14) . . ?
C21 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?
O20 C23 H23A 109.5 . . ?
O20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 118.51(14) . . ?
C25 C24 C4 122.38(14) . . ?
C29 C24 C4 118.94(13) . . ?
C24 C25 C26 120.83(15) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27 C26 C25 119.86(14) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
O27 C27 C26 124.89(14) . . ?
O27 C27 C28 115.32(14) . . ?
C26 C27 C28 119.80(14) . . ?
C29 C28 C27 119.97(15) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C24 121.01(14) . . ?
C28 C29 H29 119.5 . . ?
C24 C29 H29 119.5 . . ?
O27 C30 H30A 109.5 . . ?
O27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C8A O1 P2 118.63(9) . . ?
C12 O12 H12 111.3(15) . . ?
C20 O20 C23 116.75(13) . . ?
C27 O27 C30 117.13(13) . . ?
O2 P2 O1 110.71(6) . . ?
O2 P2 C3 114.79(6) . . ?
O1 P2 C3 99.21(6) . . ?
O2 P2 C9 114.09(6) . . ?
O1 P2 C9 98.64(6) . . ?
C3 P2 C9 116.74(7) . . ?

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2299772'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2023-10-07 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'2-(1-(2-hydroxyphenyl)-1-(p-tolyl)ethyl)-4-(p-tolyl)benzo[e][1,2]oxaphosphinine 2-oxide '
_chemical_name_common            ?
_chemical_melting_point          492
_chemical_formula_moiety         'C30 H27 O3 P'
_chemical_formula_sum            'C30 H27 O3 P'
_chemical_formula_weight         466.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.552(6)
_cell_length_b                   18.511(4)
_cell_length_c                   11.652(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.119(16)
_cell_angle_gamma                90
_cell_volume                     2381.2(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    135(2)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      32.39

_exptl_crystal_description       formless
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_T_max  0.7302
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      135(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            77457
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.134
_diffrn_reflns_theta_max         32.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8158
_reflns_number_gt                5495
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+1.7996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8158
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.70212(16) 0.35099(11) 0.58511(16) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.775169 0.359123 0.644016 0.034 Uiso 1 1 calc R U . . .
C4 C 0.69739(16) 0.36114(10) 0.46840(16) 0.0254(3) Uani 1 1 d . . . . .
C4A C 0.58543(16) 0.34807(10) 0.36933(16) 0.0258(3) Uani 1 1 d . . . . .
C5 C 0.58444(18) 0.34876(11) 0.24885(17) 0.0317(4) Uani 1 1 d . . . . .
H5 H 0.655956 0.358332 0.230387 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4794(2) 0.33551(12) 0.15646(18) 0.0388(5) Uani 1 1 d . . . . .
H6 H 0.480661 0.336880 0.077044 0.047 Uiso 1 1 calc R U . . .
C7 C 0.3724(2) 0.32018(12) 0.18286(19) 0.0394(5) Uani 1 1 d . . . . .
H7 H 0.301816 0.311390 0.120959 0.047 Uiso 1 1 calc R U . . .
C8 C 0.37028(18) 0.31794(12) 0.30079(18) 0.0347(4) Uani 1 1 d . . . . .
H8 H 0.298808 0.307401 0.318710 0.042 Uiso 1 1 calc R U . . .
C8A C 0.47625(17) 0.33163(11) 0.39225(16) 0.0285(4) Uani 1 1 d . . . . .
C9 C 0.54308(15) 0.39437(10) 0.72495(15) 0.0229(3) Uani 1 1 d . . . . .
C10 C 0.51766(17) 0.46460(11) 0.64978(17) 0.0305(4) Uani 1 1 d . . . . .
H10A H 0.442509 0.459902 0.587072 0.046 Uiso 1 1 calc R U . . .
H10B H 0.582153 0.472965 0.614962 0.046 Uiso 1 1 calc R U . . .
H10C H 0.512531 0.504520 0.700651 0.046 Uiso 1 1 calc R U . . .
C11 C 0.65815(15) 0.40027(10) 0.83349(15) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.69086(18) 0.34657(11) 0.92295(17) 0.0315(4) Uani 1 1 d . . . . .
C13 C 0.7937(2) 0.35577(14) 1.02131(19) 0.0424(5) Uani 1 1 d . . . . .
H13 H 0.812518 0.321028 1.081634 0.051 Uiso 1 1 calc R U . . .
C14 C 0.86730(19) 0.41469(15) 1.03087(19) 0.0435(5) Uani 1 1 d . . . . .
H14 H 0.935837 0.419562 1.096628 0.052 Uiso 1 1 calc R U . . .
C15 C 0.83934(18) 0.46688(13) 0.94246(18) 0.0372(5) Uani 1 1 d . . . . .
H15 H 0.889693 0.506701 0.947543 0.045 Uiso 1 1 calc R U . . .
C16 C 0.73523(17) 0.45958(11) 0.84553(16) 0.0283(4) Uani 1 1 d . . . . .
H16 H 0.716542 0.495397 0.786986 0.034 Uiso 1 1 calc R U . . .
C17 C 0.43006(16) 0.37910(10) 0.76557(16) 0.0253(3) Uani 1 1 d . . . . .
C18 C 0.3412(2) 0.32975(12) 0.7095(2) 0.0405(5) Uani 1 1 d . . . . .
H18 H 0.351673 0.301230 0.647646 0.049 Uiso 1 1 calc R U . . .
C19 C 0.2361(2) 0.32214(13) 0.7444(2) 0.0416(5) Uani 1 1 d . . . . .
H19 H 0.178487 0.288019 0.706386 0.050 Uiso 1 1 calc R U . . .
C20 C 0.21627(17) 0.36443(11) 0.83449(19) 0.0333(4) Uani 1 1 d . . . . .
C21 C 0.30429(18) 0.41475(13) 0.88943(18) 0.0355(4) Uani 1 1 d . . . . .
H21 H 0.292599 0.444126 0.949814 0.043 Uiso 1 1 calc R U . . .
C22 C 0.40970(17) 0.42199(12) 0.85570(16) 0.0307(4) Uani 1 1 d . . . . .
H22 H 0.467383 0.456013 0.894001 0.037 Uiso 1 1 calc R U . . .
C23 C 0.1008(2) 0.35667(14) 0.8700(2) 0.0450(6) Uani 1 1 d . . . . .
H23A H 0.120370 0.341987 0.952542 0.067 Uiso 1 1 calc R U . . .
H23B H 0.049699 0.320943 0.820111 0.067 Uiso 1 1 calc R U . . .
H23C H 0.059080 0.402164 0.859891 0.067 Uiso 1 1 calc R U . . .
C24 C 0.80842(16) 0.38463(10) 0.43870(15) 0.0255(3) Uani 1 1 d . . . . .
C25 C 0.91561(17) 0.34587(11) 0.48175(18) 0.0309(4) Uani 1 1 d . . . . .
H25 H 0.917501 0.304962 0.528597 0.037 Uiso 1 1 calc R U . . .
C26 C 1.01982(17) 0.36782(11) 0.45530(18) 0.0327(4) Uani 1 1 d . . . . .
H26 H 1.090521 0.340924 0.483577 0.039 Uiso 1 1 calc R U . . .
C27 C 1.01995(17) 0.42912(11) 0.38748(17) 0.0308(4) Uani 1 1 d . . . . .
C28 C 0.91342(18) 0.46841(11) 0.34657(17) 0.0323(4) Uani 1 1 d . . . . .
H28 H 0.912328 0.510122 0.301772 0.039 Uiso 1 1 calc R U . . .
C29 C 0.80868(18) 0.44647(11) 0.37140(17) 0.0307(4) Uani 1 1 d . . . . .
H29 H 0.738032 0.473367 0.342787 0.037 Uiso 1 1 calc R U . . .
C30 C 1.1330(2) 0.45127(14) 0.3569(2) 0.0426(5) Uani 1 1 d . . . . .
H30A H 1.140685 0.422925 0.290558 0.064 Uiso 1 1 calc R U . . .
H30B H 1.202408 0.443497 0.425249 0.064 Uiso 1 1 calc R U . . .
H30C H 1.127875 0.501502 0.335507 0.064 Uiso 1 1 calc R U . . .
O1 O 0.46672(12) 0.32869(9) 0.50786(12) 0.0384(4) Uani 1 1 d . . . . .
O2 O 0.58613(13) 0.25119(8) 0.68751(14) 0.0380(3) Uani 1 1 d . . . . .
O12 O 0.62463(15) 0.28562(9) 0.92152(16) 0.0423(4) Uani 1 1 d . . . . .
P2 P 0.57626(4) 0.32311(3) 0.63011(4) 0.02811(12) Uani 1 1 d . . . . .
H12 H 0.594(3) 0.2701(17) 0.844(3) 0.068(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 C4 1.358(2) . ?
C3 P2 1.7616(19) . ?
C3 H3 0.9300 . ?
C4 C4A 1.478(3) . ?
C4 C24 1.488(2) . ?
C4A C8A 1.397(3) . ?
C4A C5 1.401(2) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C8A 1.389(3) . ?
C8 H8 0.9300 . ?
C8A O1 1.384(2) . ?
C9 C17 1.540(2) . ?
C9 C11 1.545(3) . ?
C9 C10 1.547(3) . ?
C9 P2 1.8325(18) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.394(3) . ?
C11 C12 1.409(3) . ?
C12 O12 1.361(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 C22 1.391(3) . ?
C18 C19 1.396(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(3) . ?
C20 C23 1.516(3) . ?
C21 C22 1.392(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C29 1.388(3) . ?
C24 C25 1.391(3) . ?
C25 C26 1.388(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.388(3) . ?
C27 C30 1.508(3) . ?
C28 C29 1.385(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
O1 P2 1.6061(16) . ?
O2 P2 1.4792(16) . ?
O12 H12 0.91(3) . ?

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
C4 C3 P2 123.04(14) . . ?
C4 C3 H3 118.5 . . ?
P2 C3 H3 118.5 . . ?
C3 C4 C4A 121.83(16) . . ?
C3 C4 C24 119.34(16) . . ?
C4A C4 C24 118.82(15) . . ?
C8A C4A C5 116.87(17) . . ?
C8A C4A C4 121.19(16) . . ?
C5 C4A C4 121.89(16) . . ?
C6 C5 C4A 121.59(19) . . ?
C6 C5 H5 119.2 . . ?
C4A C5 H5 119.2 . . ?
C5 C6 C7 119.79(19) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.25(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C8A 119.20(19) . . ?
C7 C8 H8 120.4 . . ?
C8A C8 H8 120.4 . . ?
O1 C8A C8 115.77(17) . . ?
O1 C8A C4A 121.95(16) . . ?
C8 C8A C4A 122.28(18) . . ?
C17 C9 C11 111.36(14) . . ?
C17 C9 C10 106.95(14) . . ?
C11 C9 C10 112.23(15) . . ?
C17 C9 P2 113.57(12) . . ?
C11 C9 P2 105.20(12) . . ?
C10 C9 P2 107.59(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 117.18(17) . . ?
C16 C11 C9 120.52(16) . . ?
C12 C11 C9 122.29(16) . . ?
O12 C12 C13 116.77(19) . . ?
O12 C12 C11 123.27(18) . . ?
C13 C12 C11 119.93(19) . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 122.09(19) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
C18 C17 C22 117.75(17) . . ?
C18 C17 C9 123.63(16) . . ?
C22 C17 C9 118.32(16) . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 117.88(17) . . ?
C19 C20 C23 120.7(2) . . ?
C21 C20 C23 121.45(19) . . ?
C20 C21 C22 121.15(19) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 120.99(19) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C25 118.66(17) . . ?
C29 C24 C4 121.17(17) . . ?
C25 C24 C4 120.14(17) . . ?
C26 C25 C24 120.47(18) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C27 C26 C25 120.91(18) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 118.45(17) . . ?
C26 C27 C30 120.31(19) . . ?
C28 C27 C30 121.23(19) . . ?
C29 C28 C27 121.03(19) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C24 120.47(18) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C8A O1 P2 126.72(12) . . ?
C12 O12 H12 109(2) . . ?
O2 P2 O1 113.24(9) . . ?
O2 P2 C3 115.96(9) . . ?
O1 P2 C3 102.77(9) . . ?
O2 P2 C9 112.16(8) . . ?
O1 P2 C9 103.80(8) . . ?
C3 P2 C9 107.82(9) . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2299775'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2023-10-07 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'4-(p-tolyl)benzo[e][1,2]oxaphosphinine 2-oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 O2 P'
_chemical_formula_sum            'C15 H13 O2 P'
_chemical_formula_weight         256.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0159(7)
_cell_length_b                   4.4255(3)
_cell_length_c                   25.0968(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.518(3)
_cell_angle_gamma                90
_cell_volume                     1222.31(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      35.08

_exptl_crystal_description       formless
_exptl_crystal_colour            colorless?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7163

_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45212
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         31.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4248
_reflns_number_gt                3876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.5897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4248
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.36830(10) 0.6252(3) 0.68175(4) 0.0155(2) Uani 1 1 d . . . . .
H3 H 0.422632 0.688833 0.709990 0.019 Uiso 1 1 calc R U . . .
C4 C 0.41217(9) 0.4645(3) 0.64104(4) 0.01380(19) Uani 1 1 d . . . . .
C4A C 0.33363(10) 0.3663(3) 0.59520(4) 0.01409(19) Uani 1 1 d . . . . .
C5 C 0.37330(11) 0.1579(3) 0.55750(5) 0.0174(2) Uani 1 1 d . . . . .
H5 H 0.453648 0.080368 0.561159 0.021 Uiso 1 1 calc R U . . .
C6 C 0.29789(12) 0.0626(3) 0.51501(5) 0.0210(2) Uani 1 1 d . . . . .
H6 H 0.326921 -0.077334 0.489839 0.025 Uiso 1 1 calc R U . . .
C7 C 0.17952(12) 0.1726(3) 0.50939(5) 0.0219(2) Uani 1 1 d . . . . .
H7 H 0.127781 0.107691 0.480340 0.026 Uiso 1 1 calc R U . . .
C8 C 0.13712(11) 0.3768(3) 0.54618(5) 0.0201(2) Uani 1 1 d . . . . .
H8 H 0.056272 0.451130 0.542589 0.024 Uiso 1 1 calc R U . . .
C8A C 0.21402(10) 0.4718(3) 0.58840(4) 0.0154(2) Uani 1 1 d . . . . .
C9 C 0.54205(9) 0.3717(3) 0.64425(4) 0.01380(19) Uani 1 1 d . . . . .
C10 C 0.58651(10) 0.2094(3) 0.68858(5) 0.0164(2) Uani 1 1 d . . . . .
H10 H 0.534057 0.161790 0.716430 0.020 Uiso 1 1 calc R U . . .
C11 C 0.70743(10) 0.1170(3) 0.69220(5) 0.0189(2) Uani 1 1 d . . . . .
H11 H 0.735871 0.001417 0.722115 0.023 Uiso 1 1 calc R U . . .
C12 C 0.78749(10) 0.1909(3) 0.65271(5) 0.0184(2) Uani 1 1 d . . . . .
C13 C 0.74335(10) 0.3614(3) 0.60947(5) 0.0189(2) Uani 1 1 d . . . . .
H13 H 0.797132 0.419588 0.582733 0.023 Uiso 1 1 calc R U . . .
C14 C 0.62185(10) 0.4484(3) 0.60463(5) 0.0176(2) Uani 1 1 d . . . . .
H14 H 0.593143 0.560161 0.574313 0.021 Uiso 1 1 calc R U . . .
C15 C 0.91815(11) 0.0900(4) 0.65719(6) 0.0273(3) Uani 1 1 d . . . . .
H15A H 0.946905 0.048672 0.621513 0.041 Uiso 1 1 calc R U . . .
H15B H 0.924585 -0.093959 0.678856 0.041 Uiso 1 1 calc R U . . .
H15C H 0.967946 0.249751 0.674109 0.041 Uiso 1 1 calc R U . . .
O1 O 0.16689(8) 0.6829(2) 0.62240(3) 0.01831(18) Uani 1 1 d . . . . .
O2 O 0.14293(8) 0.5427(2) 0.72168(4) 0.01931(18) Uani 1 1 d . . . . .
P2 P 0.21352(3) 0.71997(7) 0.68399(2) 0.01436(9) Uani 1 1 d . . . . .
H2 H 0.1954(13) 1.017(3) 0.6868(5) 0.004(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 C4 1.3515(15) . ?
C3 P2 1.7591(11) . ?
C3 H3 0.9500 . ?
C4 C4A 1.4745(15) . ?
C4 C9 1.4872(15) . ?
C4A C8A 1.4013(15) . ?
C4A C5 1.4046(16) . ?
C5 C6 1.3881(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3932(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3875(19) . ?
C7 H7 0.9500 . ?
C8 C8A 1.3923(16) . ?
C8 H8 0.9500 . ?
C8A O1 1.3815(14) . ?
C9 C10 1.3947(16) . ?
C9 C14 1.3977(15) . ?
C10 C11 1.3926(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3944(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3917(18) . ?
C12 C15 1.5065(17) . ?
C13 C14 1.3928(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1 P2 1.6156(9) . ?
O2 P2 1.4766(9) . ?
P2 H2 1.330(15) . ?

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
C4 C3 P2 121.93(9) . . ?
C4 C3 H3 119.0 . . ?
P2 C3 H3 119.0 . . ?
C3 C4 C4A 121.87(10) . . ?
C3 C4 C9 118.66(10) . . ?
C4A C4 C9 119.40(9) . . ?
C8A C4A C5 117.10(10) . . ?
C8A C4A C4 120.87(10) . . ?
C5 C4A C4 122.00(10) . . ?
C6 C5 C4A 121.57(11) . . ?
C6 C5 H5 119.2 . . ?
C4A C5 H5 119.2 . . ?
C5 C6 C7 119.83(12) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.08(11) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C8A 119.46(11) . . ?
C7 C8 H8 120.3 . . ?
C8A C8 H8 120.3 . . ?
O1 C8A C8 116.21(10) . . ?
O1 C8A C4A 121.81(10) . . ?
C8 C8A C4A 121.96(11) . . ?
C10 C9 C14 118.86(10) . . ?
C10 C9 C4 119.25(10) . . ?
C14 C9 C4 121.87(10) . . ?
C11 C10 C9 120.32(11) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 121.17(11) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 118.12(11) . . ?
C13 C12 C15 121.26(12) . . ?
C11 C12 C15 120.62(12) . . ?
C12 C13 C14 121.29(11) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C9 120.19(11) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8A O1 P2 123.18(7) . . ?
O2 P2 O1 113.87(5) . . ?
O2 P2 C3 115.61(5) . . ?
O1 P2 C3 102.31(5) . . ?
O2 P2 H2 113.9(6) . . ?
O1 P2 H2 96.2(6) . . ?
C3 P2 H2 112.7(6) . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2299773'
loop_
_audit_author_name
_audit_author_address
'Igor Litvinov'
;Arbuzov Institute of Organic and Physical Chemistry RAS
Russia
;
_audit_update_record             
;
2023-10-07 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'4-(4-chlorophenyl)-2-(1-(4-chlorophenyl)-1-(2-hydroxyphenyl)ethyl)benzo[e][1,2]oxaphosphinine 2-oxide '
_chemical_name_common            ?
_chemical_melting_point          508
_chemical_formula_moiety         'C28 H21 Cl2 O3 P'
_chemical_formula_sum            'C28 H21 Cl2 O3 P'
_chemical_formula_weight         507.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.4101(5)
_cell_length_b                   18.7328(7)
_cell_length_c                   11.6060(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.346(2)
_cell_angle_gamma                90
_cell_volume                     2354.62(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    162(2)
_cell_measurement_reflns_used    9754
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      30.19

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.373
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5708
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      162(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS DIAMOND'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            90603
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.145
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6826
_reflns_number_gt                5442
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0061P)²+12.2724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6826
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.1086
_refine_ls_wR_factor_ref         0.2281
_refine_ls_wR_factor_gt          0.2217
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.7077(4) 0.6467(2) 0.5865(4) 0.0361(9) Uani 1 1 d . . . . .
H3 H 0.783668 0.637489 0.648217 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7014(4) 0.6378(2) 0.4692(4) 0.0330(9) Uani 1 1 d . . . . .
C4A C 0.5882(4) 0.6503(2) 0.3675(4) 0.0336(9) Uani 1 1 d . . . . .
C5 C 0.5864(4) 0.6491(3) 0.2470(5) 0.0408(10) Uani 1 1 d . . . . .
H5 H 0.660643 0.639123 0.229527 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4801(5) 0.6618(3) 0.1525(5) 0.0487(12) Uani 1 1 d . . . . .
H6 H 0.481186 0.660881 0.071040 0.058 Uiso 1 1 calc R U . . .
C7 C 0.3711(5) 0.6762(3) 0.1776(5) 0.0528(14) Uani 1 1 d . . . . .
H7 H 0.297088 0.684133 0.112691 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3694(4) 0.6788(3) 0.2936(5) 0.0460(12) Uani 1 1 d . . . . .
H8 H 0.294603 0.689114 0.309891 0.055 Uiso 1 1 calc R U . . .
C8A C 0.4772(4) 0.6665(2) 0.3887(5) 0.0377(10) Uani 1 1 d . . . . .
C9 C 0.5434(4) 0.6051(2) 0.7237(4) 0.0301(8) Uani 1 1 d . . . . .
C10 C 0.5160(4) 0.5360(3) 0.6477(4) 0.0376(10) Uani 1 1 d . . . . .
H10A H 0.508512 0.495981 0.699360 0.056 Uiso 1 1 calc R U . . .
H10B H 0.583542 0.526521 0.614496 0.056 Uiso 1 1 calc R U . . .
H10C H 0.438569 0.541487 0.580976 0.056 Uiso 1 1 calc R U . . .
C11 C 0.6596(4) 0.5984(2) 0.8351(4) 0.0321(9) Uani 1 1 d . . . . .
C12 C 0.6957(5) 0.6519(3) 0.9241(5) 0.0444(12) Uani 1 1 d . . . . .
C13 C 0.8013(5) 0.6422(4) 1.0239(5) 0.0578(16) Uani 1 1 d . . . . .
H13 H 0.824244 0.678255 1.084446 0.069 Uiso 1 1 calc R U . . .
C14 C 0.8722(5) 0.5826(4) 1.0370(6) 0.0649(18) Uani 1 1 d . . . . .
H14 H 0.943508 0.577134 1.105842 0.078 Uiso 1 1 calc R U . . .
C15 C 0.8395(5) 0.5302(3) 0.9493(5) 0.0524(14) Uani 1 1 d . . . . .
H15 H 0.889440 0.488797 0.956538 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7347(4) 0.5379(3) 0.8516(4) 0.0381(10) Uani 1 1 d . . . . .
H16 H 0.712310 0.500755 0.792989 0.046 Uiso 1 1 calc R U . . .
C17 C 0.4290(4) 0.6206(2) 0.7620(4) 0.0331(9) Uani 1 1 d . . . . .
C18 C 0.3419(5) 0.6722(3) 0.7083(6) 0.0544(15) Uani 1 1 d . . . . .
H18 H 0.354851 0.702202 0.647327 0.065 Uiso 1 1 calc R U . . .
C19 C 0.2362(5) 0.6811(3) 0.7417(6) 0.0580(15) Uani 1 1 d . . . . .
H19 H 0.178346 0.717525 0.705793 0.070 Uiso 1 1 calc R U . . .
C20 C 0.2166(4) 0.6362(3) 0.8276(5) 0.0469(12) Uani 1 1 d . . . . .
C21 C 0.2996(5) 0.5839(3) 0.8811(5) 0.0493(13) Uani 1 1 d . . . . .
H21 H 0.285025 0.553405 0.940570 0.059 Uiso 1 1 calc R U . . .
C22 C 0.4059(4) 0.5760(3) 0.8475(4) 0.0395(10) Uani 1 1 d . . . . .
H22 H 0.463356 0.539388 0.883711 0.047 Uiso 1 1 calc R U . . .
C23 C 0.8150(4) 0.6150(2) 0.4412(4) 0.0324(9) Uani 1 1 d . . . . .
C24 C 0.9210(4) 0.6560(3) 0.4798(5) 0.0425(11) Uani 1 1 d . . . . .
H24 H 0.921485 0.698697 0.524152 0.051 Uiso 1 1 calc R U . . .
C25 C 1.0266(4) 0.6351(3) 0.4539(5) 0.0442(12) Uani 1 1 d . . . . .
H25 H 1.099000 0.663676 0.479169 0.053 Uiso 1 1 calc R U . . .
C26 C 1.0258(4) 0.5732(3) 0.3922(5) 0.0389(10) Uani 1 1 d . . . . .
C27 C 0.9227(4) 0.5304(3) 0.3526(5) 0.0410(11) Uani 1 1 d . . . . .
H27 H 0.923577 0.487679 0.308887 0.049 Uiso 1 1 calc R U . . .
C28 C 0.8174(4) 0.5520(3) 0.3789(5) 0.0396(10) Uani 1 1 d . . . . .
H28 H 0.745463 0.523068 0.353721 0.048 Uiso 1 1 calc R U . . .
Cl20 Cl 0.08254(13) 0.64589(9) 0.86779(17) 0.0666(5) Uani 1 1 d . . . . .
Cl26 Cl 1.15839(13) 0.54732(9) 0.35923(16) 0.0616(4) Uani 1 1 d . . . . .
O1 O 0.4676(3) 0.6697(2) 0.5047(4) 0.0519(10) Uani 1 1 d . . . . .
O2 O 0.5894(3) 0.74571(18) 0.6870(4) 0.0510(10) Uani 1 1 d . . . . .
O12 O 0.6312(4) 0.7130(2) 0.9201(4) 0.0634(12) Uani 1 1 d . . . . .
H12 H 0.593567 0.723538 0.847517 0.095 Uiso 1 1 calc R U . . .
P2 P 0.57902(10) 0.67492(7) 0.62893(13) 0.0379(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 C4 1.350(7) . ?
C3 P2 1.770(4) . ?
C3 H3 0.9500 . ?
C4 C4A 1.468(6) . ?
C4 C23 1.495(6) . ?
C4A C5 1.393(7) . ?
C4A C8A 1.397(6) . ?
C5 C6 1.376(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.353(8) . ?
C7 H7 0.9500 . ?
C8 C8A 1.390(6) . ?
C8 H8 0.9500 . ?
C8A O1 1.386(6) . ?
C9 C17 1.534(5) . ?
C9 C11 1.538(6) . ?
C9 C10 1.543(6) . ?
C9 P2 1.834(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.397(6) . ?
C11 C12 1.404(6) . ?
C12 O12 1.353(6) . ?
C12 C13 1.396(8) . ?
C13 C14 1.359(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.385(7) . ?
C17 C18 1.386(7) . ?
C18 C19 1.388(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.368(8) . ?
C20 Cl20 1.743(5) . ?
C21 C22 1.395(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.383(6) . ?
C23 C28 1.389(6) . ?
C24 C25 1.387(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.361(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.377(7) . ?
C26 Cl26 1.742(4) . ?
C27 C28 1.390(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
O1 P2 1.597(4) . ?
O2 P2 1.475(4) . ?
O12 H12 0.8400 . ?

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
C4 C3 P2 122.1(3) . . ?
C4 C3 H3 119.0 . . ?
P2 C3 H3 119.0 . . ?
C3 C4 C4A 123.0(4) . . ?
C3 C4 C23 118.7(4) . . ?
C4A C4 C23 118.3(4) . . ?
C5 C4A C8A 116.9(4) . . ?
C5 C4A C4 122.4(4) . . ?
C8A C4A C4 120.6(4) . . ?
C6 C5 C4A 121.9(5) . . ?
C6 C5 H5 119.1 . . ?
C4A C5 H5 119.1 . . ?
C5 C6 C7 119.3(5) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 119.9(5) . . ?
C7 C8 H8 120.1 . . ?
C8A C8 H8 120.1 . . ?
O1 C8A C8 116.4(4) . . ?
O1 C8A C4A 122.2(4) . . ?
C8 C8A C4A 121.4(5) . . ?
C17 C9 C11 111.0(4) . . ?
C17 C9 C10 106.6(3) . . ?
C11 C9 C10 112.2(4) . . ?
C17 C9 P2 114.1(3) . . ?
C11 C9 P2 105.5(3) . . ?
C10 C9 P2 107.4(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 117.0(4) . . ?
C16 C11 C9 120.6(4) . . ?
C12 C11 C9 122.4(4) . . ?
O12 C12 C13 117.2(5) . . ?
O12 C12 C11 123.3(5) . . ?
C13 C12 C11 119.6(5) . . ?
C14 C13 C12 121.9(5) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 119.3(6) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 122.4(5) . . ?
C15 C16 H16 118.8 . . ?
C11 C16 H16 118.8 . . ?
C22 C17 C18 118.2(4) . . ?
C22 C17 C9 117.7(4) . . ?
C18 C17 C9 123.8(4) . . ?
C17 C18 C19 121.3(5) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 118.9(5) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 121.3(5) . . ?
C21 C20 Cl20 119.6(4) . . ?
C19 C20 Cl20 119.1(4) . . ?
C20 C21 C22 119.2(5) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C21 121.0(5) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C28 118.8(4) . . ?
C24 C23 C4 120.1(4) . . ?
C28 C23 C4 121.0(4) . . ?
C23 C24 C25 120.2(5) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 119.5(4) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 122.4(4) . . ?
C25 C26 Cl26 119.3(4) . . ?
C27 C26 Cl26 118.3(4) . . ?
C26 C27 C28 117.6(5) . . ?
C26 C27 H27 121.2 . . ?
C28 C27 H27 121.2 . . ?
C23 C28 C27 121.4(4) . . ?
C23 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C8A O1 P2 126.6(3) . . ?
C12 O12 H12 109.5 . . ?
O2 P2 O1 113.2(2) . . ?
O2 P2 C3 116.2(2) . . ?
O1 P2 C3 103.0(2) . . ?
O2 P2 C9 111.6(2) . . ?
O1 P2 C9 103.5(2) . . ?
C3 P2 C9 108.3(2) . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.094

