# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_1B
_database_code_depnum_ccdc_archive 'CCDC 2407184'
loop_
_audit_author_name
_audit_author_address
'Daniel Michal Kaminski'
;UMCS
Poland
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
5,10-trans-dimethyl-trans-tetradecahydrophosphanthrene 5,10-dioxide 
;
_chemical_name_common            ?
_chemical_melting_point          680
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H26 O2 P2'
_chemical_formula_weight         288.29

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'

_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                   5.648(1)
_cell_length_b                   7.599(2)
_cell_length_c                   9.119(2)
_cell_angle_alpha                83.62(2)
_cell_angle_beta                 86.36(2)
_cell_angle_gamma                72.90(2)
_cell_volume                     371.57(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    290.2(7)
_cell_measurement_reflns_used    1318
_cell_measurement_theta_min      4.8540
_cell_measurement_theta_max      75.4060

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.595
_exptl_absorpt_correction_T_min  0.75954
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      290.2(7)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2763
_diffrn_reflns_number            2234
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.882
_diffrn_reflns_theta_max         75.849
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1462
_reflns_number_gt                1266
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1193P)²+0.2415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1462
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.2053
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
C1 C 0.3383(6) 0.6346(4) 0.3650(4) 0.0367(7) Uani 1 1 d . . . . .
H1 H 0.270954 0.542011 0.330431 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6243(6) 0.5653(5) 0.3429(4) 0.0373(7) Uani 1 1 d . . . . .
H2 H 0.692901 0.655803 0.379698 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6983(8) 0.5572(7) 0.1778(4) 0.0547(10) Uani 1 1 d . . . . .
H3A H 0.877484 0.523437 0.166102 0.066 Uiso 1 1 calc R U . . .
H3B H 0.642348 0.462506 0.139858 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5866(9) 0.7423(7) 0.0888(5) 0.0642(12) Uani 1 1 d . . . . .
H4A H 0.652925 0.835189 0.121139 0.077 Uiso 1 1 calc R U . . .
H4B H 0.632177 0.731261 -0.014813 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3061(9) 0.8030(7) 0.1081(5) 0.0634(12) Uani 1 1 d . . . . .
H5A H 0.238911 0.714431 0.069496 0.076 Uiso 1 1 calc R U . . .
H5B H 0.239388 0.922217 0.052600 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2281(7) 0.8172(5) 0.2706(4) 0.0495(9) Uani 1 1 d . . . . .
H6A H 0.048779 0.851174 0.280501 0.059 Uiso 1 1 calc R U . . .
H6B H 0.282407 0.914087 0.306421 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3603(6) 0.8252(5) 0.6226(5) 0.0462(9) Uani 1 1 d . . . . .
H7A H 0.294447 0.943443 0.567980 0.069 Uiso 1 1 calc R U . . .
H7B H 0.537457 0.785990 0.609384 0.069 Uiso 1 1 calc R U . . .
H7C H 0.317035 0.834978 0.725514 0.069 Uiso 1 1 calc R U . . .
O1 O -0.0429(4) 0.7140(4) 0.5732(3) 0.0476(7) Uani 1 1 d . . . . .
P1 P 0.23308(13) 0.65883(10) 0.55699(9) 0.0357(4) 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
C1 C6 1.533(5) . ?
C1 C2 1.552(4) . ?
C1 P1 1.824(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.539(5) . ?
C2 P1 1.824(3) 2_666 ?
C2 H2 0.9800 . ?
C3 C4 1.524(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.518(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.525(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 P1 1.797(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O1 P1 1.492(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
C6 C1 C2 111.4(3) . . ?
C6 C1 P1 109.7(2) . . ?
C2 C1 P1 114.0(2) . . ?
C6 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
P1 C1 H1 107.2 . . ?
C3 C2 C1 110.8(3) . . ?
C3 C2 P1 109.4(2) . 2_666 ?
C1 C2 P1 113.9(2) . 2_666 ?
C3 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
P1 C2 H2 107.5 2_666 . ?
C4 C3 C2 111.6(4) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 110.9(4) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 110.8(3) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C1 111.8(3) . . ?
C5 C6 H6A 109.3 . . ?
C1 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C1 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
P1 C7 H7A 109.5 . . ?
P1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
P1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 P1 C7 111.80(16) . . ?
O1 P1 C2 112.10(16) . 2_666 ?
C7 P1 C2 107.78(16) . 2_666 ?
O1 P1 C1 111.77(15) . . ?
C7 P1 C1 107.53(17) . . ?
C2 P1 C1 105.52(14) 2_666 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -52.6(4) . . . . ?
P1 C1 C2 C3 -177.4(3) . . . . ?
C6 C1 C2 P1 -176.4(2) . . . 2_666 ?
P1 C1 C2 P1 58.8(3) . . . 2_666 ?
C1 C2 C3 C4 54.4(4) . . . . ?
P1 C2 C3 C4 -179.3(3) 2_666 . . . ?
C2 C3 C4 C5 -57.2(5) . . . . ?
C3 C4 C5 C6 57.8(5) . . . . ?
C4 C5 C6 C1 -56.6(5) . . . . ?
C2 C1 C6 C5 54.1(4) . . . . ?
P1 C1 C6 C5 -178.8(3) . . . . ?
C6 C1 P1 O1 58.0(3) . . . . ?
C2 C1 P1 O1 -176.4(2) . . . . ?
C6 C1 P1 C7 -65.1(3) . . . . ?
C2 C1 P1 C7 60.6(3) . . . . ?
C6 C1 P1 C2 -179.9(2) . . . 2_666 ?
C2 C1 P1 C2 -54.3(3) . . . 2_666 ?

_refine_diff_density_max         0.856
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_2B
_database_code_depnum_ccdc_archive 'CCDC 2407186'
loop_
_audit_author_name
_audit_author_address
'Daniel Kaminski'
;UMCS in Lublinie
Poland
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
5,10-trans-dicyclopentyl-trans-tradecahydrophosphanthrene 5,10-dioxide 
;
_chemical_name_common            ?
_chemical_melting_point          615.4
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H38 O2 P2'
_chemical_formula_weight         396.46

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'

_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                   5.615(1)
_cell_length_b                   9.764(3)
_cell_length_c                   10.341(3)
_cell_angle_alpha                92.98(3)
_cell_angle_beta                 103.72(3)
_cell_angle_gamma                101.25(3)
_cell_volume                     537.3(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2092
_cell_measurement_theta_min      6.0870
_cell_measurement_theta_max      73.5270

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             216
_exptl_transmission_factor_min   0.692
_exptl_transmission_factor_max   1.00
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.930

_exptl_absorpt_correction_T_min  0.78394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2763

_diffrn_reflns_number            4736
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.425
_diffrn_reflns_theta_max         76.965
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.790
_diffrn_measured_fraction_theta_full 0.845
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_Laue_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_point_group_measured_fraction_full 0.845
_reflns_number_total             1793
_reflns_number_gt                1491
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;

_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1068P)²+5.4308P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1793
_refine_ls_number_parameters     154
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.1219
_refine_ls_wR_factor_ref         0.3759
_refine_ls_wR_factor_gt          0.3684
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.002
_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
O1 O -0.0528(10) 0.3947(8) 0.3407(7) 0.058(2) Uani 1 1 d . . . . .
P1 P 0.2268(4) 0.4234(3) 0.3782(2) 0.0407(8) Uani 1 1 d . . . . .
C1 C 0.3642(16) 0.6104(11) 0.4144(9) 0.048(2) Uani 1 1 d . . . . .
H1 H 0.299351 0.644907 0.486974 0.058 Uiso 1 1 calc R U . . .
C2 C 0.6543(16) 0.6491(11) 0.4634(9) 0.046(2) Uani 1 1 d . . . . .
H2 H 0.717945 0.604205 0.395562 0.055 Uiso 1 1 calc R U . . .
C3 C 0.766(2) 0.8073(13) 0.4735(12) 0.065(3) Uani 1 1 d . . . . .
H3B H 0.727162 0.854708 0.548087 0.078 Uiso 1 1 calc R U . . .
H3A H 0.947531 0.822219 0.490973 0.078 Uiso 1 1 calc R U . . .
C4 C 0.665(2) 0.8707(14) 0.3462(12) 0.068(3) Uani 1 1 d . . . . .
H4B H 0.735752 0.970784 0.357472 0.082 Uiso 1 1 calc R U . . .
H4A H 0.716635 0.829064 0.272786 0.082 Uiso 1 1 calc R U . . .
C5 C 0.386(2) 0.8461(14) 0.3134(14) 0.075(4) Uani 1 1 d . . . . .
H5B H 0.325863 0.887941 0.232289 0.090 Uiso 1 1 calc R U . . .
H5A H 0.334834 0.890066 0.385415 0.090 Uiso 1 1 calc R U . . .
C6 C 0.273(2) 0.6885(13) 0.2937(12) 0.064(3) Uani 1 1 d . . . . .
H6B H 0.314034 0.647372 0.216481 0.077 Uiso 1 1 calc R U . . .
H6A H 0.092074 0.674669 0.274486 0.077 Uiso 1 1 calc R U . . .
C11 C 0.3487(17) 0.3509(12) 0.2474(10) 0.055(3) Uani 1 1 d D . . . .
H11 H 0.519802 0.406277 0.260857 0.066 Uiso 1 1 calc R U . A 1
C12 C 0.369(4) 0.203(2) 0.232(2) 0.061(5) Uani 0.6 1 d D . P B 1
H12A H 0.230233 0.139558 0.249445 0.073 Uiso 0.6 1 d . U P C 1
H12B H 0.525468 0.189106 0.296065 0.073 Uiso 0.6 1 d . U P D 1
C13 C 0.384(6) 0.178(3) 0.091(2) 0.083(9) Uani 0.6 1 d D . P B 1
H13A H 0.353207 0.081314 0.062151 0.099 Uiso 0.6 1 d . U P E 1
H13B H 0.556251 0.222522 0.083591 0.099 Uiso 0.6 1 d . U P F 1
C14 C 0.206(8) 0.254(4) 0.009(3) 0.094(10) Uani 0.6 1 d D . P B 1
H14A H 0.034747 0.187142 -0.016024 0.113 Uiso 0.6 1 d . U P G 1
H14B H 0.246488 0.282334 -0.068187 0.113 Uiso 0.6 1 d . U P H 1
C15 C 0.203(5) 0.377(3) 0.103(2) 0.084(7) Uani 0.6 1 d D . P B 1
H15A H 0.022777 0.375075 0.105855 0.101 Uiso 0.6 1 d . U P I 1
H15B H 0.268978 0.460175 0.075687 0.101 Uiso 0.6 1 d . U P J 1
C12A C 0.183(8) 0.198(3) 0.197(3) 0.090(12) Uani 0.4 1 d D . P B 2
H12C H 0.281010 0.133667 0.261695 0.108 Uiso 0.4 1 d . U P K 2
H12D H 0.032506 0.184922 0.200357 0.108 Uiso 0.4 1 d . U P L 2
C13A C 0.217(17) 0.170(8) 0.056(5) 0.17(4) Uani 0.4 1 d D . P B 2
H13C H 0.340502 0.094337 0.059059 0.208 Uiso 0.4 1 d . U P M 2
H13D H 0.076740 0.129336 -0.002703 0.208 Uiso 0.4 1 d . U P N 2
C14A C 0.381(12) 0.301(5) 0.029(5) 0.103(18) Uani 0.4 1 d D . P B 2
H14C H 0.286027 0.314183 -0.065762 0.123 Uiso 0.4 1 d . U P O 2
H14D H 0.540340 0.299922 0.030988 0.123 Uiso 0.4 1 d . U P P 2
C15A C 0.368(8) 0.418(4) 0.128(3) 0.090(13) Uani 0.4 1 d D . P B 2
H15C H 0.486463 0.496030 0.134252 0.108 Uiso 0.4 1 d . U P Q 2
H15D H 0.190885 0.448893 0.090795 0.108 Uiso 0.4 1 d . U P R 2


_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
O1 P1 1.491(6) . ?
P1 C1 1.819(11) . ?
P1 C11 1.824(10) . ?
P1 C2 1.848(10) 2_666 ?
C1 C6 1.532(14) . ?
C1 C2 1.550(12) . ?
C2 C3 1.538(16) . ?
C3 C4 1.518(16) . ?
C4 C5 1.490(16) . ?
C5 C6 1.529(17) . ?
C11 C15A 1.45(3) . ?
C11 C12 1.47(2) . ?
C11 C15 1.58(2) . ?
C11 C12A 1.59(3) . ?
C12 C13 1.49(3) . ?
C13 C14 1.49(3) . ?
C14 C15 1.51(3) . ?
C12A C13A 1.53(4) . ?
C13A C14A 1.51(4) . ?
C14A C15A 1.52(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 C1 112.0(4) . . ?
O1 P1 C11 111.7(4) . . ?
C1 P1 C11 109.0(5) . . ?
O1 P1 C2 111.0(4) . 2_666 ?
C1 P1 C2 103.7(4) . 2_666 ?
C11 P1 C2 109.2(5) . 2_666 ?
C6 C1 C2 110.5(8) . . ?
C6 C1 P1 110.5(7) . . ?
C2 C1 P1 115.3(7) . . ?
C3 C2 C1 113.9(8) . . ?
C3 C2 P1 110.7(7) . 2_666 ?
C1 C2 P1 112.6(7) . 2_666 ?
C4 C3 C2 111.9(9) . . ?
C5 C4 C3 110.9(10) . . ?
C4 C5 C6 110.0(10) . . ?
C5 C6 C1 114.2(9) . . ?
C12 C11 C15 103.8(14) . . ?
C15A C11 C12A 105.7(19) . . ?
C15A C11 P1 123.3(16) . . ?
C12 C11 P1 123.4(10) . . ?
C15 C11 P1 111.9(10) . . ?
C12A C11 P1 107.2(14) . . ?
C11 C12 C13 104.6(18) . . ?
C14 C13 C12 107(2) . . ?
C13 C14 C15 104.4(19) . . ?
C14 C15 C11 106.6(19) . . ?
C13A C12A C11 104(3) . . ?
C14A C13A C12A 107(4) . . ?
C13A C14A C15A 106(4) . . ?
C11 C15A C14A 104(3) . . ?

_refine_diff_density_max         1.035
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.113

####################################################################### 
# 
# 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_3B
_database_code_depnum_ccdc_archive 'CCDC 2407187'
loop_
_audit_author_name
_audit_author_address
'Daniel Kaminski'
;UMCS in Lublinie
Poland
;
_audit_update_record             
;
2024-12-03 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
5,10-cis-di-t-butyl-cis-tradecahydrophosphanthrene 5,10-dioxide 
;
_chemical_name_common            ?
_chemical_melting_point          553
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H38 O2 P2'
_chemical_formula_weight         372.44

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.5497(2)
_cell_length_b                   9.5497(2)
_cell_length_c                   23.2662(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2121.80(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      4.9740
_cell_measurement_theta_max      72.2540

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   0.635
_exptl_transmission_factor_max   1.0
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.921

_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      air

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2763

_diffrn_reflns_number            15481
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.006
_diffrn_reflns_theta_max         72.508
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2103
_reflns_number_gt                2029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'

_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0547P)²+0.4315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 769 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(11)
_chemical_absolute_configuration R
_refine_ls_number_reflns         2103
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
O1 O 0.2035(2) 0.3521(2) 0.39293(8) 0.0592(5) Uani 1 1 d . . . . .
P1 P 0.32601(7) 0.40056(7) 0.42683(3) 0.0437(2) Uani 1 1 d . . . . .
C1 C 0.4345(3) 0.2547(3) 0.45378(11) 0.0485(6) Uani 1 1 d . . . . .
H1 H 0.508194 0.241827 0.424966 0.058 Uiso 1 1 calc R U . . .
C2 C 0.5123(3) 0.2785(3) 0.51136(10) 0.0484(6) Uani 1 1 d . . . . .
H2 H 0.575577 0.357916 0.505118 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6066(4) 0.1498(4) 0.52276(14) 0.0697(9) Uani 1 1 d . . . . .
H3A H 0.681451 0.148600 0.494605 0.084 Uiso 1 1 calc R U . . .
H3B H 0.648940 0.159430 0.560444 0.084 Uiso 1 1 calc R U . . .
C4 C 0.5286(5) 0.0107(4) 0.52013(16) 0.0795(11) Uani 1 1 d . . . . .
H4A H 0.462349 0.005717 0.551680 0.095 Uiso 1 1 calc R U . . .
H4B H 0.594830 -0.065513 0.524528 0.095 Uiso 1 1 calc R U . . .
C5 C 0.4502(4) -0.0063(3) 0.46322(16) 0.0737(9) Uani 1 1 d . . . . .
H5A H 0.516680 -0.011541 0.431778 0.088 Uiso 1 1 calc R U . . .
H5B H 0.396407 -0.092465 0.463758 0.088 Uiso 1 1 calc R U . . .
C6 C 0.3527(4) 0.1175(3) 0.45427(13) 0.0595(7) Uani 1 1 d . . . . .
H6A H 0.283770 0.119859 0.484862 0.071 Uiso 1 1 calc R U . . .
H6B H 0.303466 0.106718 0.418085 0.071 Uiso 1 1 calc R U . . .
C11 C 0.4441(3) 0.5059(3) 0.38105(12) 0.0546(7) Uani 1 1 d . . . . .
C12 C 0.3688(5) 0.6406(4) 0.36279(18) 0.0868(12) Uani 1 1 d . . . . .
H12A H 0.360927 0.702242 0.395225 0.130 Uiso 1 1 calc R U . . .
H12B H 0.277004 0.617939 0.348791 0.130 Uiso 1 1 calc R U . . .
H12C H 0.421351 0.685910 0.332935 0.130 Uiso 1 1 calc R U . . .
C13 C 0.5837(4) 0.5426(5) 0.40960(15) 0.0787(11) Uani 1 1 d . . . . .
H13A H 0.638073 0.599900 0.384084 0.118 Uiso 1 1 calc R U . . .
H13B H 0.634180 0.458087 0.417986 0.118 Uiso 1 1 calc R U . . .
H13C H 0.566428 0.592779 0.444638 0.118 Uiso 1 1 calc R U . . .
C14 C 0.4735(4) 0.4180(4) 0.32718(11) 0.0691(9) Uani 1 1 d . . . . .
H14A H 0.528443 0.471794 0.300592 0.104 Uiso 1 1 calc R U . . .
H14B H 0.386530 0.392145 0.309443 0.104 Uiso 1 1 calc R U . . .
H14C H 0.524046 0.335003 0.337799 0.104 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 P1 1.485(2) . ?
P1 C1 1.846(3) . ?
P1 C2 1.848(3) 7_556 ?
P1 C11 1.849(3) . ?
C1 C6 1.525(4) . ?
C1 C2 1.549(3) . ?
C2 C3 1.546(4) . ?
C3 C4 1.524(6) . ?
C4 C5 1.530(5) . ?
C5 C6 1.519(5) . ?
C11 C13 1.530(5) . ?
C11 C12 1.534(5) . ?
C11 C14 1.535(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 C1 112.77(13) . . ?
O1 P1 C2 113.61(13) . 7_556 ?
C1 P1 C2 108.01(11) . 7_556 ?
O1 P1 C11 110.14(12) . . ?
C1 P1 C11 105.31(14) . . ?
C2 P1 C11 106.48(13) 7_556 . ?
C6 C1 C2 111.5(2) . . ?
C6 C1 P1 111.33(19) . . ?
C2 C1 P1 116.89(18) . . ?
C3 C2 C1 108.1(2) . . ?
C3 C2 P1 113.4(2) . 7_556 ?
C1 C2 P1 115.59(19) . 7_556 ?
C4 C3 C2 113.7(3) . . ?
C3 C4 C5 111.5(3) . . ?
C6 C5 C4 109.6(3) . . ?
C5 C6 C1 110.9(3) . . ?
C13 C11 C12 109.7(3) . . ?
C13 C11 C14 108.7(3) . . ?
C12 C11 C14 108.6(3) . . ?
C13 C11 P1 114.0(2) . . ?
C12 C11 P1 109.2(2) . . ?
C14 C11 P1 106.5(2) . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.037

