# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_AgLH4
_database_code_depnum_ccdc_archive 'CCDC 2505719'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H14 Ag N O8 P2, 2(H2 O)'
_chemical_formula_sum            'C4 H18 Ag N O10 P2'
_chemical_formula_weight         410.00

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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   7.2368(2)
_cell_length_b                   9.0908(2)
_cell_length_c                   19.3367(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.219(2)
_cell_angle_gamma                90
_cell_volume                     1251.95(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8358
_cell_measurement_theta_min      2.8680
_cell_measurement_theta_max      30.8800

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.175
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.911
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.71895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14668
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         30.872
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3281
_reflns_number_gt                2971
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_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)+(0.0251P)²+0.4193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3281
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0539
_refine_ls_wR_factor_gt          0.0524
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
Ag1 Ag 0.98154(2) 0.54602(2) 0.24732(2) 0.01460(6) Uani 1 1 d . . . . .
P1 P 0.61030(6) 0.39314(5) 0.32563(2) 0.00770(10) Uani 1 1 d . . . . .
P2 P 0.99828(6) 0.25332(5) 0.34267(2) 0.00773(10) Uani 1 1 d . . . . .
O1 O 0.71586(17) 0.52625(14) 0.30609(7) 0.0109(3) Uani 1 1 d . . . . .
O2 O 0.50454(17) 0.30499(15) 0.26511(7) 0.0113(3) Uani 1 1 d . . . . .
O3 O 0.47146(19) 0.45114(14) 0.37380(7) 0.0109(3) Uani 1 1 d . . . . .
O4 O 0.93089(18) 0.24889(15) 0.26057(7) 0.0109(3) Uani 1 1 d . . . . .
O5 O 1.11731(17) 0.38934(14) 0.35848(7) 0.0108(3) Uani 1 1 d . . . . .
O6 O 1.08623(17) 0.10884(14) 0.36929(7) 0.0106(3) Uani 1 1 d . . . . .
O7 O 0.70503(18) 0.12453(14) 0.37848(7) 0.0097(2) Uani 1 1 d . . . . .
O8 O 1.19443(18) 0.42796(16) 0.18759(7) 0.0121(3) Uani 1 1 d . . . . .
O9 O 0.4326(2) 0.1220(2) 0.45167(9) 0.0231(3) Uani 1 1 d . . . . .
O10 O 0.45752(19) 0.23684(18) 0.59165(8) 0.0152(3) Uani 1 1 d . . . . .
N1 N 1.1030(2) 0.16839(18) 0.62853(9) 0.0109(3) Uani 1 1 d . . . . .
C1 C 0.7812(2) 0.27156(19) 0.38087(9) 0.0079(3) Uani 1 1 d . . . . .
C2 C 0.8250(2) 0.3285(2) 0.45725(9) 0.0099(3) Uani 1 1 d . . . . .
H2A H 0.873585 0.430253 0.457111 0.012 Uiso 1 1 calc R U . . .
H2B H 0.706952 0.331639 0.476397 0.012 Uiso 1 1 calc R U . . .
C3 C 0.9687(3) 0.2338(2) 0.50582(10) 0.0134(4) Uani 1 1 d . . . . .
H3A H 0.942886 0.128552 0.494997 0.016 Uiso 1 1 calc R U . . .
H3B H 1.096337 0.256103 0.496934 0.016 Uiso 1 1 calc R U . . .
C4 C 0.9617(2) 0.2616(2) 0.58250(10) 0.0113(4) Uani 1 1 d . . . . .
H4A H 0.987666 0.366688 0.593569 0.014 Uiso 1 1 calc R U . . .
H4B H 0.834446 0.238749 0.591681 0.014 Uiso 1 1 calc R U . . .
H3 H 0.375(4) 0.424(3) 0.3683(14) 0.022(7) Uiso 1 1 d . . . . .
H4 H 0.896(4) 0.172(4) 0.2429(16) 0.043(9) Uiso 1 1 d . . . . .
H7 H 0.619(4) 0.125(3) 0.4035(15) 0.033(8) Uiso 1 1 d . . . . .
H8A H 1.262(4) 0.489(4) 0.1651(17) 0.048(9) Uiso 1 1 d . . . . .
H8B H 1.274(4) 0.379(3) 0.2136(14) 0.026(7) Uiso 1 1 d . . . . .
H9A H 0.445(4) 0.147(4) 0.4916(19) 0.044(9) Uiso 1 1 d . . . . .
H9B H 0.324(5) 0.127(3) 0.4349(16) 0.042(9) Uiso 1 1 d . . . . .
H10A H 0.537(4) 0.192(3) 0.6223(15) 0.032(7) Uiso 1 1 d . . . . .
H10B H 0.481(4) 0.315(4) 0.5962(16) 0.036(9) Uiso 1 1 d . . . . .
H1N H 1.205(4) 0.190(3) 0.6189(13) 0.020(6) Uiso 1 1 d . . . . .
H2N H 1.098(3) 0.187(3) 0.6739(15) 0.024(7) Uiso 1 1 d . . . . .
H3N H 1.081(3) 0.076(3) 0.6188(13) 0.018(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
Ag1 O8 2.3432(14) . ?
Ag1 O2 2.3704(14) 2_655 ?
Ag1 O1 2.4074(13) . ?
Ag1 O5 2.6202(13) . ?
Ag1 O7 2.6617(13) 2_655 ?
Ag1 O4 2.7440(14) . ?
P1 O2 1.5100(13) . ?
P1 O1 1.5143(14) . ?
P1 O3 1.5771(14) . ?
P1 C1 1.8504(17) . ?
P2 O5 1.5070(13) . ?
P2 O6 1.5096(13) . ?
P2 O4 1.5764(14) . ?
P2 C1 1.8579(18) . ?
O7 C1 1.444(2) . ?
N1 C4 1.494(2) . ?
C1 C2 1.544(2) . ?
C2 C3 1.536(2) . ?
C3 C4 1.514(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
O8 Ag1 O2 111.19(5) . 2_655 ?
O8 Ag1 O1 148.05(5) . . ?
O2 Ag1 O1 100.01(4) 2_655 . ?
O8 Ag1 O5 88.38(5) . . ?
O2 Ag1 O5 127.34(4) 2_655 . ?
O1 Ag1 O5 77.69(4) . . ?
O8 Ag1 O7 86.77(4) . 2_655 ?
O2 Ag1 O7 70.42(4) 2_655 2_655 ?
O1 Ag1 O7 97.66(4) . 2_655 ?
O5 Ag1 O7 162.01(4) . 2_655 ?
O8 Ag1 O4 72.87(4) . . ?
O2 Ag1 O4 174.82(4) 2_655 . ?
O1 Ag1 O4 75.60(4) . . ?
O5 Ag1 O4 54.91(4) . . ?
O7 Ag1 O4 107.15(4) 2_655 . ?
O2 P1 O1 116.07(8) . . ?
O2 P1 O3 110.29(7) . . ?
O1 P1 O3 106.42(8) . . ?
O2 P1 C1 108.99(8) . . ?
O1 P1 C1 107.83(7) . . ?
O3 P1 C1 106.83(8) . . ?
O5 P2 O6 116.96(7) . . ?
O5 P2 O4 106.79(7) . . ?
O6 P2 O4 110.95(7) . . ?
O5 P2 C1 109.83(8) . . ?
O6 P2 C1 106.09(8) . . ?
O4 P2 C1 105.68(7) . . ?
P1 O1 Ag1 131.14(8) . . ?
P1 O2 Ag1 125.51(7) . 2_645 ?
P2 O4 Ag1 92.66(6) . . ?
P2 O5 Ag1 99.32(6) . . ?
O7 C1 C2 110.68(14) . . ?
O7 C1 P1 108.80(11) . . ?
C2 C1 P1 110.78(12) . . ?
O7 C1 P2 104.47(11) . . ?
C2 C1 P2 111.45(11) . . ?
P1 C1 P2 110.46(9) . . ?
C3 C2 C1 113.52(14) . . ?
C4 C3 C2 111.64(15) . . ?
N1 C4 C3 110.50(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O5 0.73(3) 1.87(3) 2.5889(18) 169(3) 1_455 yes
O4 H4 O1 0.80(3) 1.74(3) 2.5299(18) 168(3) 2_645 yes
O7 H7 O9 0.86(3) 1.77(3) 2.623(2) 177(3) . yes
O8 H8A O6 0.90(4) 1.76(4) 2.6557(19) 173(3) 2_755 yes
O8 H8B O2 0.82(3) 1.91(3) 2.7091(18) 164(3) 1_655 yes
O9 H9A O10 0.80(4) 2.09(4) 2.877(2) 173(3) . yes
O9 H9B O6 0.79(3) 1.96(3) 2.723(2) 162(3) 1_455 yes
O10 H10A O8 0.85(3) 1.89(3) 2.738(2) 173(3) 4_566 yes
O10 H10B O3 0.73(3) 2.22(3) 2.938(2) 170(3) 3_666 yes
N1 H1N O10 0.82(3) 2.04(3) 2.851(2) 178(3) 1_655 yes
N1 H2N O2 0.90(3) 2.00(3) 2.865(2) 161(2) 4_666 yes
N1 H3N O6 0.87(3) 2.10(3) 2.872(2) 147(2) 3_756 yes

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_compound1a_Ph4PLH4
_database_code_depnum_ccdc_archive 'CCDC 2505724'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_CF_05_25a_auto      
;
PROBLEM: Hirshfeld Test Diff for    P1       --O1       .       10.5 s.u.  
RESPONSE: Manual inspection of the displacement ellipsoids did not indicate 
any problems.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H20 P), 2(C4 H12 N O7 P2), H2 O'
_chemical_formula_sum            'C56 H66 N2 O15 P6'
_chemical_formula_weight         1192.92

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'
N N 0.0311 0.0180 '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                   9.40710(10)
_cell_length_b                   9.74440(10)
_cell_length_c                   14.7719(2)
_cell_angle_alpha                89.7180(10)
_cell_angle_beta                 88.3120(10)
_cell_angle_gamma                88.2130(10)
_cell_volume                     1352.83(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    18690
_cell_measurement_theta_min      4.5100
_cell_measurement_theta_max      79.4450

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             626
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    2.459
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81437
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            28796
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.540
_diffrn_reflns_theta_max         80.268
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5783
_reflns_number_gt                5308
_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 1.171.43.95a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0480P)²+0.6646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         5783
_refine_ls_number_parameters     402
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
P1 P 0.18554(4) 0.88291(4) 0.40552(3) 0.02346(11) Uani 1 1 d . . . . .
P2 P 0.13325(4) 0.57850(4) 0.37127(3) 0.01958(10) Uani 1 1 d . . . . .
P3 P 0.39787(4) 0.25394(4) 0.90534(2) 0.01683(10) Uani 1 1 d . . . . .
O1 O 0.17391(12) 0.88662(11) 0.30094(8) 0.0247(2) Uani 1 1 d D . . . .
O2 O 0.28555(12) 0.98570(11) 0.43912(9) 0.0266(3) Uani 1 1 d . . . . .
O3 O 0.03502(12) 0.89556(13) 0.45042(9) 0.0300(3) Uani 1 1 d . . . . .
O4 O 0.10119(12) 0.64042(11) 0.27735(7) 0.0233(2) Uani 1 1 d D . . . .
O5 O 0.20653(12) 0.43958(11) 0.36541(8) 0.0237(2) Uani 1 1 d . . . . .
O6 O -0.00598(11) 0.57667(12) 0.42951(8) 0.0236(2) Uani 1 1 d . . . . .
O7 O 0.23269(14) 0.67704(15) 0.52525(8) 0.0317(3) Uani 1 1 d . . . . .
O8 O 0.0040(3) 0.7591(3) 0.63130(17) 0.0323(5) Uani 0.5 1 d D . P . .
N1 N 0.76575(14) 0.75245(14) 0.49581(11) 0.0235(3) Uani 1 1 d . . . . .
C1 C 0.24554(15) 0.70328(16) 0.42968(10) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.40302(15) 0.67676(15) 0.40222(11) 0.0208(3) Uani 1 1 d . . . . .
H2A H 0.421372 0.576341 0.398251 0.025 Uiso 1 1 calc R U . . .
H2B H 0.420210 0.715800 0.341020 0.025 Uiso 1 1 calc R U . . .
C3 C 0.50946(16) 0.73627(16) 0.46613(11) 0.0234(3) Uani 1 1 d . . . . .
H3A H 0.493463 0.836959 0.470433 0.028 Uiso 1 1 calc R U . . .
H3B H 0.495615 0.696450 0.527425 0.028 Uiso 1 1 calc R U . . .
C4 C 0.66023(16) 0.70412(16) 0.43123(12) 0.0240(3) Uani 1 1 d . . . . .
H4A H 0.673606 0.603807 0.422616 0.029 Uiso 1 1 calc R U . . .
H4B H 0.675781 0.749412 0.371779 0.029 Uiso 1 1 calc R U . . .
C5 C 0.37813(16) 0.40989(15) 0.84048(10) 0.0196(3) Uani 1 1 d . . . . .
C6 C 0.24749(17) 0.43742(16) 0.80013(12) 0.0248(3) Uani 1 1 d . . . . .
H6 H 0.168076 0.382705 0.814624 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2347(2) 0.54488(17) 0.73897(12) 0.0286(4) Uani 1 1 d . . . . .
H7 H 0.145894 0.565045 0.712122 0.034 Uiso 1 1 calc R U . . .
C8 C 0.3517(2) 0.62320(16) 0.71686(11) 0.0276(3) Uani 1 1 d . . . . .
H8 H 0.343519 0.694313 0.672918 0.033 Uiso 1 1 calc R U . . .
C9 C 0.47997(19) 0.59842(16) 0.75836(11) 0.0260(3) Uani 1 1 d . . . . .
H9 H 0.558834 0.653997 0.744135 0.031 Uiso 1 1 calc R U . . .
C10 C 0.49326(17) 0.49207(16) 0.82090(11) 0.0222(3) Uani 1 1 d . . . . .
H10 H 0.580778 0.475609 0.850160 0.027 Uiso 1 1 calc R U . . .
C11 C 0.57623(16) 0.23685(14) 0.94603(10) 0.0183(3) Uani 1 1 d . . . . .
C12 C 0.69337(17) 0.24167(16) 0.88537(10) 0.0216(3) Uani 1 1 d . . . . .
H12 H 0.679101 0.250929 0.822206 0.026 Uiso 1 1 calc R U . . .
C13 C 0.82958(17) 0.23290(17) 0.91770(11) 0.0249(3) Uani 1 1 d . . . . .
H13 H 0.908937 0.235932 0.876533 0.030 Uiso 1 1 calc R U . . .
C14 C 0.85151(17) 0.21969(17) 1.00999(11) 0.0247(3) Uani 1 1 d . . . . .
H14 H 0.945553 0.213548 1.031718 0.030 Uiso 1 1 calc R U . . .
C15 C 0.73615(17) 0.21549(16) 1.07026(11) 0.0232(3) Uani 1 1 d . . . . .
H15 H 0.751295 0.206414 1.133337 0.028 Uiso 1 1 calc R U . . .
C16 C 0.59869(16) 0.22447(15) 1.03899(10) 0.0201(3) Uani 1 1 d . . . . .
H16 H 0.519828 0.222230 1.080600 0.024 Uiso 1 1 calc R U . . .
C17 C 0.27877(15) 0.25619(15) 1.00217(10) 0.0198(3) Uani 1 1 d . . . . .
C18 C 0.22713(16) 0.38182(16) 1.03790(11) 0.0229(3) Uani 1 1 d . . . . .
H18 H 0.239759 0.464636 1.004850 0.027 Uiso 1 1 calc R U . . .
C19 C 0.15728(19) 0.38394(18) 1.12218(13) 0.0297(4) Uani 1 1 d . . . . .
H19 H 0.121586 0.468478 1.146842 0.036 Uiso 1 1 calc R U . . .
C20 C 0.13963(19) 0.26269(19) 1.17032(12) 0.0307(4) Uani 1 1 d . . . . .
H20 H 0.093854 0.265139 1.228509 0.037 Uiso 1 1 calc R U . . .
C21 C 0.18822(18) 0.13767(18) 1.13433(12) 0.0269(3) Uani 1 1 d . . . . .
H21 H 0.173984 0.055025 1.167280 0.032 Uiso 1 1 calc R U . . .
C22 C 0.25740(17) 0.13401(16) 1.05031(11) 0.0236(3) Uani 1 1 d . . . . .
H22 H 0.290338 0.048746 1.025346 0.028 Uiso 1 1 calc R U . . .
C23 C 0.35644(16) 0.11870(14) 0.82916(10) 0.0189(3) Uani 1 1 d . . . . .
C24 C 0.21231(17) 0.09688(16) 0.81411(11) 0.0234(3) Uani 1 1 d . . . . .
H24 H 0.141116 0.134081 0.854685 0.028 Uiso 1 1 calc R U . . .
C25 C 0.17380(19) 0.02115(17) 0.74013(12) 0.0282(3) Uani 1 1 d . . . . .
H25 H 0.076156 0.007188 0.729656 0.034 Uiso 1 1 calc R U . . .
C26 C 0.2777(2) -0.03430(16) 0.68137(12) 0.0282(3) Uani 1 1 d . . . . .
H26 H 0.250890 -0.083337 0.629445 0.034 Uiso 1 1 calc R U . . .
C27 C 0.42085(19) -0.01838(16) 0.69815(11) 0.0262(3) Uani 1 1 d . . . . .
H27 H 0.491527 -0.060028 0.659084 0.031 Uiso 1 1 calc R U . . .
C28 C 0.46111(17) 0.05800(15) 0.77164(11) 0.0219(3) Uani 1 1 d . . . . .
H28 H 0.559007 0.069029 0.782849 0.026 Uiso 1 1 calc R U . . .
H1 H 0.144(5) 0.811(3) 0.282(3) 0.039(12) Uiso 0.5 1 d D . P A 1
H3 H 0.015(6) 0.975(6) 0.476(4) 0.050(15) Uiso 0.5 1 d . . P B -2
H4 H 0.116(6) 0.726(2) 0.281(4) 0.047(14) Uiso 0.5 1 d D . P C 2
H6A H 0.004(5) 0.524(5) 0.471(3) 0.031(12) Uiso 0.5 1 d . . P D -1
H7A H 0.147(4) 0.680(4) 0.539(2) 0.082(11) Uiso 1 1 d . . . . .
H8B H -0.069(4) 0.707(4) 0.631(3) 0.039(12) Uiso 0.5 1 d D . P . .
H8A H -0.015(10) 0.836(5) 0.604(6) 0.13(3) Uiso 0.5 1 d D . P . .
H1N H 0.771(3) 0.692(3) 0.5486(17) 0.040(6) Uiso 1 1 d . . . . .
H2N H 0.853(3) 0.750(2) 0.4696(17) 0.039(6) Uiso 1 1 d . . . . .
H3N H 0.743(3) 0.839(3) 0.5168(17) 0.041(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
P1 O2 1.4919(11) . ?
P1 O3 1.5475(12) . ?
P1 O1 1.5521(12) . ?
P1 C1 1.8585(16) . ?
P2 O5 1.5015(11) . ?
P2 O4 1.5443(12) . ?
P2 O6 1.5462(11) . ?
P2 C1 1.8663(16) . ?
P3 C17 1.7905(15) . ?
P3 C23 1.7966(15) . ?
P3 C5 1.8001(15) . ?
P3 C11 1.8014(15) . ?
O7 C1 1.4357(18) . ?
N1 C4 1.485(2) . ?
C1 C2 1.539(2) . ?
C2 C3 1.526(2) . ?
C3 C4 1.519(2) . ?
C5 C10 1.390(2) . ?
C5 C6 1.399(2) . ?
C6 C7 1.384(2) . ?
C7 C8 1.389(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.390(2) . ?
C11 C16 1.400(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.381(2) . ?
C13 C14 1.390(2) . ?
C14 C15 1.385(2) . ?
C15 C16 1.386(2) . ?
C17 C22 1.401(2) . ?
C17 C18 1.403(2) . ?
C18 C19 1.390(2) . ?
C19 C20 1.388(3) . ?
C20 C21 1.390(2) . ?
C21 C22 1.384(2) . ?
C23 C28 1.400(2) . ?
C23 C24 1.403(2) . ?
C24 C25 1.385(2) . ?
C25 C26 1.386(3) . ?
C26 C27 1.390(3) . ?
C27 C28 1.388(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
O2 P1 O3 113.45(7) . . ?
O2 P1 O1 112.54(7) . . ?
O3 P1 O1 109.60(7) . . ?
O2 P1 C1 112.55(7) . . ?
O3 P1 C1 104.25(7) . . ?
O1 P1 C1 103.70(6) . . ?
O5 P2 O4 112.76(7) . . ?
O5 P2 O6 112.36(6) . . ?
O4 P2 O6 109.20(7) . . ?
O5 P2 C1 110.96(7) . . ?
O4 P2 C1 106.74(6) . . ?
O6 P2 C1 104.34(7) . . ?
C17 P3 C23 110.85(7) . . ?
C17 P3 C5 110.87(7) . . ?
C23 P3 C5 105.20(7) . . ?
C17 P3 C11 107.45(7) . . ?
C23 P3 C11 112.59(7) . . ?
C5 P3 C11 109.93(7) . . ?
O7 C1 C2 106.70(12) . . ?
O7 C1 P1 109.60(10) . . ?
C2 C1 P1 111.98(10) . . ?
O7 C1 P2 107.70(10) . . ?
C2 C1 P2 109.74(10) . . ?
P1 C1 P2 110.95(8) . . ?
C3 C2 C1 115.11(12) . . ?
C4 C3 C2 109.91(13) . . ?
N1 C4 C3 110.82(13) . . ?
C10 C5 C6 120.14(14) . . ?
C10 C5 P3 121.44(12) . . ?
C6 C5 P3 117.92(12) . . ?
C7 C6 C5 119.59(15) . . ?
C6 C7 C8 120.03(16) . . ?
C9 C8 C7 120.48(15) . . ?
C8 C9 C10 119.88(16) . . ?
C5 C10 C9 119.80(15) . . ?
C16 C11 C12 119.55(14) . . ?
C16 C11 P3 120.05(11) . . ?
C12 C11 P3 120.34(12) . . ?
C13 C12 C11 119.78(14) . . ?
C12 C13 C14 120.52(15) . . ?
C15 C14 C13 119.94(15) . . ?
C14 C15 C16 120.31(15) . . ?
C15 C16 C11 119.90(14) . . ?
C22 C17 C18 120.13(14) . . ?
C22 C17 P3 119.04(11) . . ?
C18 C17 P3 119.95(12) . . ?
C19 C18 C17 119.35(15) . . ?
C20 C19 C18 120.07(15) . . ?
C19 C20 C21 120.72(16) . . ?
C22 C21 C20 119.79(16) . . ?
C21 C22 C17 119.90(15) . . ?
C28 C23 C24 119.68(14) . . ?
C28 C23 P3 121.24(12) . . ?
C24 C23 P3 117.58(11) . . ?
C25 C24 C23 120.03(15) . . ?
C24 C25 C26 120.03(16) . . ?
C25 C26 C27 120.23(15) . . ?
C28 C27 C26 120.36(15) . . ?
C27 C28 C23 119.55(15) . . ?

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
O2 P1 C1 O7 69.96(12) . . . . ?
O3 P1 C1 O7 -53.42(11) . . . . ?
O1 P1 C1 O7 -168.14(10) . . . . ?
O2 P1 C1 C2 -48.24(13) . . . . ?
O3 P1 C1 C2 -171.62(10) . . . . ?
O1 P1 C1 C2 73.66(11) . . . . ?
O2 P1 C1 P2 -171.23(7) . . . . ?
O3 P1 C1 P2 65.39(9) . . . . ?
O1 P1 C1 P2 -49.32(9) . . . . ?
O5 P2 C1 O7 -78.13(11) . . . . ?
O4 P2 C1 O7 158.65(10) . . . . ?
O6 P2 C1 O7 43.09(12) . . . . ?
O5 P2 C1 C2 37.65(12) . . . . ?
O4 P2 C1 C2 -85.57(11) . . . . ?
O6 P2 C1 C2 158.87(10) . . . . ?
O5 P2 C1 P1 161.92(7) . . . . ?
O4 P2 C1 P1 38.70(9) . . . . ?
O6 P2 C1 P1 -76.86(8) . . . . ?
O7 C1 C2 C3 -44.23(17) . . . . ?
P1 C1 C2 C3 75.68(15) . . . . ?
P2 C1 C2 C3 -160.64(11) . . . . ?
C1 C2 C3 C4 -179.56(13) . . . . ?
C2 C3 C4 N1 -175.96(13) . . . . ?
C17 P3 C5 C10 124.16(13) . . . . ?
C23 P3 C5 C10 -115.96(13) . . . . ?
C11 P3 C5 C10 5.50(15) . . . . ?
C17 P3 C5 C6 -63.98(14) . . . . ?
C23 P3 C5 C6 55.90(14) . . . . ?
C11 P3 C5 C6 177.37(12) . . . . ?
C10 C5 C6 C7 1.6(2) . . . . ?
P3 C5 C6 C7 -170.41(13) . . . . ?
C5 C6 C7 C8 1.0(2) . . . . ?
C6 C7 C8 C9 -2.7(3) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C6 C5 C10 C9 -2.5(2) . . . . ?
P3 C5 C10 C9 169.14(12) . . . . ?
C8 C9 C10 C5 0.9(2) . . . . ?
C17 P3 C11 C16 1.72(14) . . . . ?
C23 P3 C11 C16 -120.62(12) . . . . ?
C5 P3 C11 C16 122.45(12) . . . . ?
C17 P3 C11 C12 -175.58(12) . . . . ?
C23 P3 C11 C12 62.09(14) . . . . ?
C5 P3 C11 C12 -54.85(14) . . . . ?
C16 C11 C12 C13 0.6(2) . . . . ?
P3 C11 C12 C13 177.91(12) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C11 0.5(2) . . . . ?
C12 C11 C16 C15 -0.7(2) . . . . ?
P3 C11 C16 C15 -178.06(12) . . . . ?
C23 P3 C17 C22 50.60(14) . . . . ?
C5 P3 C17 C22 167.04(12) . . . . ?
C11 P3 C17 C22 -72.81(14) . . . . ?
C23 P3 C17 C18 -140.10(13) . . . . ?
C5 P3 C17 C18 -23.65(15) . . . . ?
C11 P3 C17 C18 96.49(14) . . . . ?
C22 C17 C18 C19 1.3(2) . . . . ?
P3 C17 C18 C19 -167.90(13) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 -1.5(3) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
C20 C21 C22 C17 0.3(3) . . . . ?
C18 C17 C22 C21 -1.6(2) . . . . ?
P3 C17 C22 C21 167.71(13) . . . . ?
C17 P3 C23 C28 -152.82(12) . . . . ?
C5 P3 C23 C28 87.28(14) . . . . ?
C11 P3 C23 C28 -32.43(15) . . . . ?
C17 P3 C23 C24 41.21(14) . . . . ?
C5 P3 C23 C24 -78.68(13) . . . . ?
C11 P3 C23 C24 161.61(12) . . . . ?
C28 C23 C24 C25 -3.1(2) . . . . ?
P3 C23 C24 C25 163.08(13) . . . . ?
C23 C24 C25 C26 0.6(2) . . . . ?
C24 C25 C26 C27 2.3(3) . . . . ?
C25 C26 C27 C28 -2.8(3) . . . . ?
C26 C27 C28 C23 0.2(2) . . . . ?
C24 C23 C28 C27 2.7(2) . . . . ?
P3 C23 C28 C27 -163.00(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1^a O4 0.856(19) 1.72(3) 2.5436(16) 161(5) . yes
O3 H3^b O3 0.88(5) 1.71(5) 2.571(2) 165(6) 2_576 yes
O4 H4^b O1 0.86(2) 1.70(2) 2.5436(16) 168(6) . yes
O6 H6A^a O6 0.80(4) 1.77(4) 2.560(2) 172(5) 2_566 yes
O7 H7A O8 0.83(4) 2.02(4) 2.725(3) 143(3) . yes
O8 H8B O5 0.872(19) 1.95(2) 2.812(3) 169(5) 2_566 yes
O8 H8A O3 0.87(2) 2.37(8) 2.989(3) 128(8) . yes
N1 H1N O5 0.98(3) 1.81(3) 2.7813(19) 172(2) 2_666 yes
N1 H2N O6 0.90(3) 2.18(2) 2.8579(18) 131(2) 1_655 yes
N1 H3N O2 0.91(3) 1.84(3) 2.7545(18) 175(2) 2_676 yes

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.056

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_compound4_Ph3PPrLH4
_database_code_depnum_ccdc_archive 'CCDC 2505725'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 P, C4 H12 N O7 P2, H2 O'
_chemical_formula_sum            'C25 H36 N O8 P3'
_chemical_formula_weight         571.46

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'
N N 0.0311 0.0180 '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                   9.10010(10)
_cell_length_b                   9.25410(10)
_cell_length_c                   16.7568(2)
_cell_angle_alpha                80.0400(10)
_cell_angle_beta                 76.6860(10)
_cell_angle_gamma                81.9090(10)
_cell_volume                     1345.00(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    19820
_cell_measurement_theta_min      4.8640
_cell_measurement_theta_max      79.7890

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.092
_exptl_absorpt_coefficient_mu    2.456
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.74955
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            28493
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0328
_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       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.879
_diffrn_reflns_theta_max         80.182
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5771
_reflns_number_gt                5459
_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 system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_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)+(0.0478P)²+0.6141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         5771
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
P1 P 0.72023(4) 1.04814(3) 0.34057(2) 0.01380(9) Uani 1 1 d . . . . .
P2 P 0.73737(3) 0.72153(3) 0.38793(2) 0.01337(9) Uani 1 1 d . . . . .
O1 O 0.76585(11) 1.19175(10) 0.35119(6) 0.0189(2) Uani 1 1 d . . . . .
O2 O 0.75273(11) 1.00781(11) 0.25432(6) 0.0187(2) Uani 1 1 d . . . . .
O3 O 0.54214(11) 1.04706(11) 0.38164(6) 0.0194(2) Uani 1 1 d . . . . .
O4 O 0.79810(11) 0.58196(10) 0.43369(6) 0.01832(19) Uani 1 1 d . . . . .
O5 O 0.81123(11) 0.72288(11) 0.29123(6) 0.0191(2) Uani 1 1 d . . . . .
O6 O 0.56648(11) 0.75449(11) 0.40093(6) 0.0209(2) Uani 1 1 d . . . . .
O7 O 0.74288(11) 0.91223(10) 0.49359(5) 0.01571(18) Uani 1 1 d . . . . .
N1 N 1.29384(12) 0.69353(12) 0.49968(7) 0.0151(2) Uani 1 1 d . . . . .
C1 C 0.80149(14) 0.89108(14) 0.40832(7) 0.0130(2) Uani 1 1 d . . . . .
C2 C 0.97460(14) 0.88885(14) 0.39308(8) 0.0140(2) Uani 1 1 d . . . . .
H2A H 1.020147 0.859033 0.337975 0.017 Uiso 1 1 calc R U . . .
H2B H 0.999549 0.990092 0.391753 0.017 Uiso 1 1 calc R U . . .
C3 C 1.04692(14) 0.78452(14) 0.45849(8) 0.0149(2) Uani 1 1 d . . . . .
H3A H 1.008988 0.817959 0.513284 0.018 Uiso 1 1 calc R U . . .
H3B H 1.018590 0.683629 0.462645 0.018 Uiso 1 1 calc R U . . .
C4 C 1.21808(14) 0.78305(14) 0.43436(8) 0.0145(2) Uani 1 1 d . . . . .
H4A H 1.255927 0.741844 0.381766 0.017 Uiso 1 1 calc R U . . .
H4B H 1.244990 0.885534 0.424928 0.017 Uiso 1 1 calc R U . . .
P3 P 0.57707(4) 0.27814(3) 0.85116(2) 0.01388(9) Uani 1 1 d . . . . .
C5 C 0.64283(15) 0.40774(14) 0.76247(8) 0.0146(2) Uani 1 1 d . . . . .
C6 C 0.54025(15) 0.50188(15) 0.72164(8) 0.0179(3) Uani 1 1 d . . . . .
H6 H 0.433975 0.498367 0.741046 0.021 Uiso 1 1 calc R U . . .
C7 C 0.59574(16) 0.60053(15) 0.65239(8) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.527089 0.664298 0.623900 0.024 Uiso 1 1 calc R U . . .
C8 C 0.75106(16) 0.60639(15) 0.62459(8) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.787903 0.675589 0.577823 0.023 Uiso 1 1 calc R U . . .
C9 C 0.85316(15) 0.51188(15) 0.66460(8) 0.0184(3) Uani 1 1 d . . . . .
H9 H 0.959314 0.515762 0.644807 0.022 Uiso 1 1 calc R U . . .
C10 C 0.79967(15) 0.41197(15) 0.73345(8) 0.0171(3) Uani 1 1 d . . . . .
H10 H 0.868948 0.346714 0.760808 0.021 Uiso 1 1 calc R U . . .
C11 C 0.63580(16) 0.32141(15) 0.93908(8) 0.0183(3) Uani 1 1 d . . . . .
C12 C 0.72270(17) 0.43799(16) 0.93005(9) 0.0229(3) Uani 1 1 d . . . . .
H12 H 0.738858 0.504563 0.879665 0.027 Uiso 1 1 calc R U . . .
C13 C 0.78580(19) 0.45618(18) 0.99562(10) 0.0282(3) Uani 1 1 d . . . . .
H13 H 0.845870 0.535042 0.989510 0.034 Uiso 1 1 calc R U . . .
C14 C 0.76169(19) 0.36041(18) 1.06944(10) 0.0297(3) Uani 1 1 d . . . . .
H14 H 0.807563 0.372075 1.113129 0.036 Uiso 1 1 calc R U . . .
C15 C 0.6706(2) 0.24731(18) 1.07982(9) 0.0298(3) Uani 1 1 d . . . . .
H15 H 0.651372 0.183625 1.131167 0.036 Uiso 1 1 calc R U . . .
C16 C 0.60777(18) 0.22758(16) 1.01496(9) 0.0246(3) Uani 1 1 d . . . . .
H16 H 0.545490 0.150175 1.021995 0.029 Uiso 1 1 calc R U . . .
C17 C 0.66699(15) 0.09727(14) 0.83294(8) 0.0160(2) Uani 1 1 d . . . . .
C18 C 0.80650(16) 0.04646(15) 0.85464(8) 0.0198(3) Uani 1 1 d . . . . .
H18 H 0.848044 0.101703 0.885277 0.024 Uiso 1 1 calc R U . . .
C19 C 0.88439(16) -0.08506(16) 0.83132(9) 0.0233(3) Uani 1 1 d . . . . .
H19 H 0.980046 -0.119065 0.845272 0.028 Uiso 1 1 calc R U . . .
C20 C 0.82243(17) -0.16675(16) 0.78766(10) 0.0255(3) Uani 1 1 d . . . . .
H20 H 0.875224 -0.257197 0.772249 0.031 Uiso 1 1 calc R U . . .
C21 C 0.68349(19) -0.11649(18) 0.76647(10) 0.0292(3) Uani 1 1 d . . . . .
H21 H 0.641516 -0.172918 0.736660 0.035 Uiso 1 1 calc R U . . .
C22 C 0.60535(17) 0.01560(16) 0.78851(9) 0.0235(3) Uani 1 1 d . . . . .
H22 H 0.510680 0.050099 0.773455 0.028 Uiso 1 1 calc R U . . .
C23 C 0.37457(15) 0.28146(15) 0.86424(8) 0.0178(3) Uani 1 1 d . . . . .
H23A H 0.328261 0.383853 0.869010 0.021 Uiso 1 1 calc R U . . .
H23B H 0.353649 0.255284 0.813391 0.021 Uiso 1 1 calc R U . . .
C24 C 0.29497(16) 0.17943(16) 0.93876(9) 0.0232(3) Uani 1 1 d . . . . .
H24A H 0.350775 0.079439 0.940643 0.028 Uiso 1 1 calc R U . . .
H24B H 0.295119 0.217036 0.990574 0.028 Uiso 1 1 calc R U . . .
C25 C 0.13196(18) 0.1713(2) 0.93254(10) 0.0310(3) Uani 1 1 d . . . . .
H25A H 0.132237 0.122049 0.885207 0.046 Uiso 1 1 calc R U . . .
H25B H 0.079958 0.271267 0.924843 0.046 Uiso 1 1 calc R U . . .
H25C H 0.078857 0.115260 0.983578 0.046 Uiso 1 1 calc R U . . .
O8 O 0.86373(13) 1.43081(13) 0.23122(6) 0.0240(2) Uani 1 1 d . . . . .
H3 H 0.524(3) 0.956(3) 0.3877(14) 0.040(6) Uiso 1 1 d . . . . .
H5 H 0.797(3) 0.809(3) 0.2680(14) 0.041(6) Uiso 1 1 d . . . . .
H7A H 0.654(3) 0.913(2) 0.5053(12) 0.030(5) Uiso 1 1 d . . . . .
H8A H 0.850(3) 1.507(3) 0.2548(15) 0.047(6) Uiso 1 1 d . . . . .
H8B H 0.835(3) 1.360(3) 0.2707(15) 0.048(6) Uiso 1 1 d . . . . .
H1N H 1.265(2) 0.598(2) 0.5153(12) 0.030(5) Uiso 1 1 d . . . . .
H2N H 1.394(2) 0.692(2) 0.4796(12) 0.025(4) Uiso 1 1 d . . . . .
H3N H 1.274(2) 0.738(2) 0.5459(12) 0.024(4) 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
P1 O1 1.4972(10) . ?
P1 O2 1.5080(10) . ?
P1 O3 1.6090(10) . ?
P1 C1 1.8606(13) . ?
P2 O4 1.4877(10) . ?
P2 O6 1.5140(10) . ?
P2 O5 1.6035(10) . ?
P2 C1 1.8586(13) . ?
O7 C1 1.4424(14) . ?
N1 C4 1.4942(16) . ?
C1 C2 1.5345(16) . ?
C2 C3 1.5343(17) . ?
C3 C4 1.5152(16) . ?
P3 C5 1.7835(13) . ?
P3 C17 1.8001(13) . ?
P3 C11 1.8009(13) . ?
P3 C23 1.8015(13) . ?
C5 C6 1.3992(18) . ?
C5 C10 1.4017(18) . ?
C6 C7 1.3886(19) . ?
C7 C8 1.388(2) . ?
C8 C9 1.3903(19) . ?
C9 C10 1.3863(19) . ?
C11 C12 1.393(2) . ?
C11 C16 1.4025(19) . ?
C12 C13 1.395(2) . ?
C13 C14 1.384(2) . ?
C14 C15 1.388(2) . ?
C15 C16 1.388(2) . ?
C17 C22 1.3952(19) . ?
C17 C18 1.3966(18) . ?
C18 C19 1.389(2) . ?
C19 C20 1.388(2) . ?
C20 C21 1.387(2) . ?
C21 C22 1.388(2) . ?
C23 C24 1.5308(19) . ?
C24 C25 1.524(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
O1 P1 O2 118.19(6) . . ?
O1 P1 O3 107.15(6) . . ?
O2 P1 O3 110.29(5) . . ?
O1 P1 C1 111.34(5) . . ?
O2 P1 C1 107.80(5) . . ?
O3 P1 C1 100.66(5) . . ?
O4 P2 O6 117.35(6) . . ?
O4 P2 O5 107.87(6) . . ?
O6 P2 O5 110.23(6) . . ?
O4 P2 C1 114.52(5) . . ?
O6 P2 C1 104.17(6) . . ?
O5 P2 C1 101.54(5) . . ?
O7 C1 C2 106.50(9) . . ?
O7 C1 P2 110.34(8) . . ?
C2 C1 P2 114.11(8) . . ?
O7 C1 P1 108.60(8) . . ?
C2 C1 P1 110.70(8) . . ?
P2 C1 P1 106.53(6) . . ?
C3 C2 C1 114.02(10) . . ?
C4 C3 C2 109.57(10) . . ?
N1 C4 C3 111.87(10) . . ?
C5 P3 C17 108.57(6) . . ?
C5 P3 C11 108.94(6) . . ?
C17 P3 C11 107.41(6) . . ?
C5 P3 C23 108.17(6) . . ?
C17 P3 C23 109.51(6) . . ?
C11 P3 C23 114.13(6) . . ?
C6 C5 C10 120.45(12) . . ?
C6 C5 P3 120.82(10) . . ?
C10 C5 P3 118.73(10) . . ?
C7 C6 C5 119.17(12) . . ?
C8 C7 C6 120.31(12) . . ?
C7 C8 C9 120.58(12) . . ?
C10 C9 C8 119.83(12) . . ?
C9 C10 C5 119.65(12) . . ?
C12 C11 C16 119.62(13) . . ?
C12 C11 P3 120.46(10) . . ?
C16 C11 P3 119.57(11) . . ?
C11 C12 C13 119.47(14) . . ?
C14 C13 C12 120.60(15) . . ?
C13 C14 C15 120.15(14) . . ?
C16 C15 C14 119.80(14) . . ?
C15 C16 C11 120.29(15) . . ?
C22 C17 C18 120.09(13) . . ?
C22 C17 P3 119.41(10) . . ?
C18 C17 P3 120.09(10) . . ?
C19 C18 C17 119.86(13) . . ?
C20 C19 C18 119.99(13) . . ?
C21 C20 C19 120.09(13) . . ?
C20 C21 C22 120.51(14) . . ?
C21 C22 C17 119.45(13) . . ?
C24 C23 P3 116.39(10) . . ?
C25 C24 C23 110.37(12) . . ?

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
O4 P2 C1 O7 -65.32(10) . . . . ?
O6 P2 C1 O7 64.18(9) . . . . ?
O5 P2 C1 O7 178.73(8) . . . . ?
O4 P2 C1 C2 54.52(10) . . . . ?
O6 P2 C1 C2 -175.98(8) . . . . ?
O5 P2 C1 C2 -61.43(9) . . . . ?
O4 P2 C1 P1 176.98(5) . . . . ?
O6 P2 C1 P1 -53.52(7) . . . . ?
O5 P2 C1 P1 61.03(7) . . . . ?
O1 P1 C1 O7 61.68(9) . . . . ?
O2 P1 C1 O7 -167.16(8) . . . . ?
O3 P1 C1 O7 -51.63(9) . . . . ?
O1 P1 C1 C2 -54.90(10) . . . . ?
O2 P1 C1 C2 76.27(9) . . . . ?
O3 P1 C1 C2 -168.20(8) . . . . ?
O1 P1 C1 P2 -179.48(6) . . . . ?
O2 P1 C1 P2 -48.32(7) . . . . ?
O3 P1 C1 P2 67.21(7) . . . . ?
O7 C1 C2 C3 49.73(13) . . . . ?
P2 C1 C2 C3 -72.25(12) . . . . ?
P1 C1 C2 C3 167.60(9) . . . . ?
C1 C2 C3 C4 176.16(10) . . . . ?
C2 C3 C4 N1 174.94(10) . . . . ?
C17 P3 C5 C6 125.59(11) . . . . ?
C11 P3 C5 C6 -117.73(11) . . . . ?
C23 P3 C5 C6 6.84(13) . . . . ?
C17 P3 C5 C10 -53.35(11) . . . . ?
C11 P3 C5 C10 63.33(12) . . . . ?
C23 P3 C5 C10 -172.10(10) . . . . ?
C10 C5 C6 C7 -0.6(2) . . . . ?
P3 C5 C6 C7 -179.48(10) . . . . ?
C5 C6 C7 C8 -0.6(2) . . . . ?
C6 C7 C8 C9 1.3(2) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C8 C9 C10 C5 -0.40(19) . . . . ?
C6 C5 C10 C9 1.05(19) . . . . ?
P3 C5 C10 C9 180.00(10) . . . . ?
C5 P3 C11 C12 -1.81(14) . . . . ?
C17 P3 C11 C12 115.61(12) . . . . ?
C23 P3 C11 C12 -122.79(12) . . . . ?
C5 P3 C11 C16 -174.95(11) . . . . ?
C17 P3 C11 C16 -57.54(13) . . . . ?
C23 P3 C11 C16 64.06(13) . . . . ?
C16 C11 C12 C13 2.6(2) . . . . ?
P3 C11 C12 C13 -170.56(12) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 C15 -1.8(2) . . . . ?
C13 C14 C15 C16 2.1(2) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C12 C11 C16 C15 -2.3(2) . . . . ?
P3 C11 C16 C15 170.90(12) . . . . ?
C5 P3 C17 C22 -83.74(12) . . . . ?
C11 P3 C17 C22 158.60(11) . . . . ?
C23 P3 C17 C22 34.16(13) . . . . ?
C5 P3 C17 C18 88.89(12) . . . . ?
C11 P3 C17 C18 -28.76(13) . . . . ?
C23 P3 C17 C18 -153.21(11) . . . . ?
C22 C17 C18 C19 0.5(2) . . . . ?
P3 C17 C18 C19 -172.08(11) . . . . ?
C17 C18 C19 C20 -1.0(2) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C20 C21 C22 C17 -0.6(2) . . . . ?
C18 C17 C22 C21 0.3(2) . . . . ?
P3 C17 C22 C21 172.90(12) . . . . ?
C5 P3 C23 C24 -178.73(10) . . . . ?
C17 P3 C23 C24 63.12(12) . . . . ?
C11 P3 C23 C24 -57.31(12) . . . . ?
P3 C23 C24 C25 -168.96(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O6 0.87(2) 1.84(2) 2.6543(14) 157(2) . yes
O5 H5 O2 0.83(2) 1.81(2) 2.6098(14) 160(2) . yes
O7 H7A O3 0.78(2) 2.33(2) 2.9564(13) 137.9(19) 2_676 yes
O8 H8A O5 0.85(3) 2.15(3) 2.9833(15) 169(2) 1_565 yes
O8 H8B O1 0.87(3) 1.95(3) 2.8143(14) 175(2) . yes
N1 H1N O4 0.93(2) 1.84(2) 2.7626(14) 169.1(18) 2_766 yes
N1 H2N O6 0.90(2) 1.89(2) 2.7188(15) 153.1(17) 1_655 yes
N1 H3N O1 0.91(2) 1.89(2) 2.7923(15) 173.2(17) 2_776 yes

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_compound1_Ph4PLH4
_database_code_depnum_ccdc_archive 'CCDC 2505726'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 P, C4 H12 N O7 P2, 6(H2 O)'
_chemical_formula_sum            'C28 H44 N O13 P3'
_chemical_formula_weight         695.55

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'
N N 0.0311 0.0180 '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                   10.0191(2)
_cell_length_b                   11.5988(2)
_cell_length_c                   15.4510(3)
_cell_angle_alpha                75.289(2)
_cell_angle_beta                 73.302(2)
_cell_angle_gamma                82.836(2)
_cell_volume                     1660.87(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    22954
_cell_measurement_theta_min      3.9410
_cell_measurement_theta_max      79.6800

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.205
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81144
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            34649
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.947
_diffrn_reflns_theta_max         80.588
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7111
_reflns_number_gt                6471
_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 system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_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)+(0.0549P)²+0.5515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         7111
_refine_ls_number_parameters     478
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0921
_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
P1 P 0.67083(3) 0.36101(3) 0.14232(2) 0.01549(9) Uani 1 1 d . . . . .
P2 P 0.54243(3) 0.61557(3) 0.11700(2) 0.01495(9) Uani 1 1 d . . . . .
P3 P 1.15712(3) 0.21855(3) 0.51686(2) 0.01713(9) Uani 1 1 d . . . . .
O1 O 0.60249(11) 0.36342(9) 0.24770(7) 0.0207(2) Uani 1 1 d . . . . .
O2 O 0.56708(10) 0.32157(8) 0.10255(7) 0.0204(2) Uani 1 1 d . . . . .
O3 O 0.80574(10) 0.28702(8) 0.13415(7) 0.0210(2) Uani 1 1 d . . . . .
O4 O 0.48032(10) 0.57000(9) 0.21930(7) 0.0200(2) Uani 1 1 d . . . . .
O5 O 0.44188(10) 0.58774(8) 0.06369(7) 0.01849(19) Uani 1 1 d . . . . .
O6 O 0.57168(10) 0.74669(8) 0.08498(7) 0.01933(19) Uani 1 1 d . . . . .
O7 O 0.74978(10) 0.53427(8) -0.01403(6) 0.01797(19) Uani 1 1 d . . . . .
O8 O 0.35260(11) 0.88808(9) 0.02699(8) 0.0235(2) Uani 1 1 d . . . . .
O9 O 0.62795(12) 0.87783(11) 0.20164(8) 0.0297(2) Uani 1 1 d . . . . .
O10 O 0.88900(13) 0.95727(11) 0.09477(10) 0.0359(3) Uani 1 1 d . . . . .
O11 O 0.47551(14) 1.09462(11) 0.17470(10) 0.0378(3) Uani 1 1 d . . . . .
O12 O 0.27597(11) 1.10609(10) 0.08038(8) 0.0261(2) Uani 1 1 d . . . . .
O13 O 0.98939(13) 1.09459(10) 0.18006(8) 0.0289(2) Uani 1 1 d . . . . .
N1 N 1.09452(13) 0.78935(11) 0.03291(9) 0.0210(2) Uani 1 1 d . . . . .
C1 C 0.70389(13) 0.52091(11) 0.08507(9) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.82510(14) 0.55263(12) 0.11615(9) 0.0181(2) Uani 1 1 d . . . . .
H2A H 0.789300 0.558358 0.181760 0.022 Uiso 1 1 calc R U . . .
H2B H 0.896933 0.485801 0.113835 0.022 Uiso 1 1 calc R U . . .
C3 C 0.89569(14) 0.66771(12) 0.06018(10) 0.0198(3) Uani 1 1 d . . . . .
H3A H 0.928457 0.665452 -0.006258 0.024 Uiso 1 1 calc R U . . .
H3B H 0.827461 0.736645 0.066186 0.024 Uiso 1 1 calc R U . . .
C4 C 1.01896(14) 0.68311(12) 0.09444(10) 0.0200(3) Uani 1 1 d . . . . .
H4A H 0.985378 0.693786 0.158897 0.024 Uiso 1 1 calc R U . . .
H4B H 1.083008 0.610864 0.094188 0.024 Uiso 1 1 calc R U . . .
C5 C 0.99328(14) 0.20891(13) 0.60353(9) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.94038(16) 0.30636(14) 0.64384(10) 0.0256(3) Uani 1 1 d . . . . .
H6 H 0.993030 0.375059 0.627272 0.031 Uiso 1 1 calc R U . . .
C7 C 0.81069(17) 0.30196(15) 0.70806(11) 0.0312(3) Uani 1 1 d . . . . .
H7 H 0.773538 0.368139 0.734966 0.037 Uiso 1 1 calc R U . . .
C8 C 0.73544(16) 0.20043(17) 0.73286(11) 0.0312(3) Uani 1 1 d . . . . .
H8 H 0.646318 0.197896 0.776432 0.037 Uiso 1 1 calc R U . . .
C9 C 0.78876(17) 0.10272(16) 0.69481(11) 0.0314(3) Uani 1 1 d . . . . .
H9 H 0.737241 0.033075 0.713378 0.038 Uiso 1 1 calc R U . . .
C10 C 0.91765(16) 0.10679(14) 0.62950(10) 0.0264(3) Uani 1 1 d . . . . .
H10 H 0.954058 0.040422 0.602685 0.032 Uiso 1 1 calc R U . . .
C11 C 1.24624(14) 0.07358(12) 0.53045(10) 0.0208(3) Uani 1 1 d . . . . .
C12 C 1.24003(16) 0.00503(14) 0.61989(11) 0.0270(3) Uani 1 1 d . . . . .
H12 H 1.188155 0.034532 0.672513 0.032 Uiso 1 1 calc R U . . .
C13 C 1.31009(17) -0.10639(14) 0.63138(13) 0.0328(3) Uani 1 1 d . . . . .
H13 H 1.306895 -0.153211 0.692017 0.039 Uiso 1 1 calc R U . . .
C14 C 1.38476(17) -0.14945(14) 0.55442(13) 0.0327(4) Uani 1 1 d . . . . .
H14 H 1.433037 -0.225622 0.562701 0.039 Uiso 1 1 calc R U . . .
C15 C 1.38977(17) -0.08266(15) 0.46561(13) 0.0310(3) Uani 1 1 d . . . . .
H15 H 1.440088 -0.113668 0.413404 0.037 Uiso 1 1 calc R U . . .
C16 C 1.32116(15) 0.02995(14) 0.45264(11) 0.0247(3) Uani 1 1 d . . . . .
H16 H 1.325154 0.076507 0.391812 0.030 Uiso 1 1 calc R U . . .
C17 C 1.13115(14) 0.26727(12) 0.40317(9) 0.0193(3) Uani 1 1 d . . . . .
C18 C 1.24643(15) 0.30322(13) 0.32747(10) 0.0234(3) Uani 1 1 d . . . . .
H18 H 1.336116 0.302255 0.337042 0.028 Uiso 1 1 calc R U . . .
C19 C 1.22852(16) 0.34011(14) 0.23871(10) 0.0260(3) Uani 1 1 d . . . . .
H19 H 1.306099 0.364150 0.187119 0.031 Uiso 1 1 calc R U . . .
C20 C 1.09661(16) 0.34189(14) 0.22529(10) 0.0260(3) Uani 1 1 d . . . . .
H20 H 1.084693 0.367144 0.164347 0.031 Uiso 1 1 calc R U . . .
C21 C 0.98226(16) 0.30709(15) 0.30013(10) 0.0268(3) Uani 1 1 d . . . . .
H21 H 0.892522 0.309273 0.290334 0.032 Uiso 1 1 calc R U . . .
C22 C 0.99928(15) 0.26907(13) 0.38937(10) 0.0230(3) Uani 1 1 d . . . . .
H22 H 0.921511 0.244458 0.440669 0.028 Uiso 1 1 calc R U . . .
C23 C 1.25078(14) 0.32817(12) 0.53578(9) 0.0202(3) Uani 1 1 d . . . . .
C24 C 1.24332(16) 0.44685(13) 0.48683(11) 0.0252(3) Uani 1 1 d . . . . .
H24 H 1.202314 0.467564 0.436220 0.030 Uiso 1 1 calc R U . . .
C25 C 1.29606(18) 0.53429(14) 0.51246(12) 0.0319(3) Uani 1 1 d . . . . .
H25 H 1.291371 0.615166 0.479400 0.038 Uiso 1 1 calc R U . . .
C26 C 1.35576(19) 0.50337(16) 0.58657(12) 0.0345(4) Uani 1 1 d . . . . .
H26 H 1.390056 0.563665 0.604834 0.041 Uiso 1 1 calc R U . . .
C27 C 1.36576(17) 0.38527(15) 0.63417(11) 0.0301(3) Uani 1 1 d . . . . .
H27 H 1.409153 0.364785 0.683630 0.036 Uiso 1 1 calc R U . . .
C28 C 1.31249(15) 0.29692(14) 0.60966(10) 0.0234(3) Uani 1 1 d . . . . .
H28 H 1.317900 0.216110 0.642730 0.028 Uiso 1 1 calc R U . . .
H1 H 0.555(3) 0.425(2) 0.2492(16) 0.040(6) Uiso 1 1 d . . . . .
H5 H 0.453(3) 0.625(2) 0.0057(19) 0.050(7) Uiso 1 1 d . . . . .
H7A H 0.685(3) 0.513(2) -0.0311(16) 0.043(6) Uiso 1 1 d . . . . .
H8A H 0.384(3) 0.901(2) -0.034(2) 0.051(7) Uiso 1 1 d . . . . .
H8B H 0.413(3) 0.847(2) 0.0494(17) 0.045(6) Uiso 1 1 d . . . . .
H9A H 0.576(3) 0.948(3) 0.1924(19) 0.056(7) Uiso 1 1 d . . . . .
H9B H 0.603(3) 0.837(2) 0.1730(17) 0.044(6) Uiso 1 1 d . . . . .
H10A H 0.809(3) 0.929(2) 0.1333(18) 0.047(6) Uiso 1 1 d . . . . .
H10B H 0.918(3) 0.998(3) 0.128(2) 0.070(9) Uiso 1 1 d . . . . .
H11A H 0.406(3) 1.096(2) 0.1529(17) 0.047(6) Uiso 1 1 d . . . . .
H11B H 0.501(3) 1.169(3) 0.1611(18) 0.054(7) Uiso 1 1 d . . . . .
H12A H 0.314(3) 1.161(2) 0.0301(18) 0.043(6) Uiso 1 1 d . . . . .
H12B H 0.293(3) 1.042(2) 0.0616(17) 0.046(6) Uiso 1 1 d . . . . .
H13A H 0.944(3) 1.158(2) 0.1709(17) 0.047(7) Uiso 1 1 d . . . . .
H13B H 1.074(3) 1.108(2) 0.1504(18) 0.050(7) Uiso 1 1 d . . . . .
H1N H 1.126(2) 0.7805(18) -0.0275(15) 0.029(5) Uiso 1 1 d . . . . .
H2N H 1.169(2) 0.8045(18) 0.0490(14) 0.029(5) Uiso 1 1 d . . . . .
H3N H 1.036(2) 0.854(2) 0.0366(15) 0.034(5) 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
P1 O3 1.4990(10) . ?
P1 O2 1.5153(9) . ?
P1 O1 1.5807(10) . ?
P1 C1 1.8664(13) . ?
P2 O4 1.5025(10) . ?
P2 O6 1.5130(10) . ?
P2 O5 1.5781(9) . ?
P2 C1 1.8545(13) . ?
P3 C17 1.7873(14) . ?
P3 C5 1.7908(14) . ?
P3 C11 1.7952(14) . ?
P3 C23 1.7963(14) . ?
O7 C1 1.4396(15) . ?
N1 C4 1.4898(18) . ?
C1 C2 1.5418(17) . ?
C2 C3 1.5256(18) . ?
C3 C4 1.5219(18) . ?
C5 C10 1.395(2) . ?
C5 C6 1.402(2) . ?
C6 C7 1.388(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.389(2) . ?
C11 C12 1.397(2) . ?
C11 C16 1.400(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.386(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.393(2) . ?
C17 C22 1.3943(19) . ?
C17 C18 1.4043(19) . ?
C18 C19 1.386(2) . ?
C19 C20 1.392(2) . ?
C20 C21 1.389(2) . ?
C21 C22 1.390(2) . ?
C23 C24 1.397(2) . ?
C23 C28 1.399(2) . ?
C24 C25 1.387(2) . ?
C25 C26 1.389(2) . ?
C26 C27 1.387(3) . ?
C27 C28 1.388(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
O3 P1 O2 114.81(6) . . ?
O3 P1 O1 109.11(6) . . ?
O2 P1 O1 110.15(6) . . ?
O3 P1 C1 110.45(6) . . ?
O2 P1 C1 108.33(6) . . ?
O1 P1 C1 103.38(5) . . ?
O4 P2 O6 116.30(5) . . ?
O4 P2 O5 108.24(5) . . ?
O6 P2 O5 109.20(5) . . ?
O4 P2 C1 106.24(6) . . ?
O6 P2 C1 111.07(6) . . ?
O5 P2 C1 105.17(5) . . ?
C17 P3 C5 110.67(6) . . ?
C17 P3 C11 110.43(6) . . ?
C5 P3 C11 108.09(7) . . ?
C17 P3 C23 108.81(7) . . ?
C5 P3 C23 106.57(6) . . ?
C11 P3 C23 112.22(6) . . ?
O7 C1 C2 107.57(10) . . ?
O7 C1 P2 110.34(8) . . ?
C2 C1 P2 112.69(8) . . ?
O7 C1 P1 109.31(8) . . ?
C2 C1 P1 106.90(8) . . ?
P2 C1 P1 109.92(6) . . ?
C3 C2 C1 116.43(11) . . ?
C4 C3 C2 110.58(11) . . ?
N1 C4 C3 109.55(11) . . ?
C10 C5 C6 120.23(13) . . ?
C10 C5 P3 120.60(11) . . ?
C6 C5 P3 119.15(11) . . ?
C7 C6 C5 119.66(14) . . ?
C6 C7 C8 119.74(15) . . ?
C9 C8 C7 120.82(14) . . ?
C8 C9 C10 119.91(15) . . ?
C9 C10 C5 119.61(14) . . ?
C12 C11 C16 120.46(13) . . ?
C12 C11 P3 118.97(11) . . ?
C16 C11 P3 120.57(11) . . ?
C13 C12 C11 119.57(15) . . ?
C14 C13 C12 120.01(16) . . ?
C15 C14 C13 120.71(14) . . ?
C14 C15 C16 120.12(15) . . ?
C15 C16 C11 119.12(15) . . ?
C22 C17 C18 120.34(13) . . ?
C22 C17 P3 120.88(11) . . ?
C18 C17 P3 118.78(10) . . ?
C19 C18 C17 119.58(13) . . ?
C18 C19 C20 119.88(14) . . ?
C21 C20 C19 120.65(14) . . ?
C20 C21 C22 119.93(14) . . ?
C21 C22 C17 119.62(13) . . ?
C24 C23 C28 120.43(13) . . ?
C24 C23 P3 120.04(11) . . ?
C28 C23 P3 118.79(11) . . ?
C25 C24 C23 119.67(14) . . ?
C24 C25 C26 119.85(15) . . ?
C27 C26 C25 120.60(14) . . ?
C26 C27 C28 120.14(15) . . ?
C27 C28 C23 119.29(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.81(3) 1.76(3) 2.5447(14) 164(2) . yes
O5 H5 O2 0.87(3) 1.69(3) 2.5395(14) 164(3) 2_665 yes
O7 H7A O5 0.85(3) 2.07(3) 2.8906(13) 163(2) 2_665 yes
O8 H8A O11 0.89(3) 2.21(3) 3.0663(19) 161(2) 2_675 yes
O8 H8B O6 0.83(3) 1.97(3) 2.7922(15) 172(2) . yes
O9 H9A O11 0.91(3) 1.87(3) 2.7757(18) 178(3) . yes
O9 H9B O6 0.82(3) 2.03(3) 2.8410(15) 170(2) . yes
O10 H10A O9 0.89(3) 1.90(3) 2.7862(18) 172(2) . yes
O10 H10B O13 0.91(3) 1.84(3) 2.7409(17) 172(3) . yes
O11 H11A O12 0.85(3) 1.92(3) 2.7654(17) 169(2) . yes
O11 H11B O2 0.88(3) 1.88(3) 2.7455(16) 166(2) 1_565 yes
O12 H12A O6 0.89(3) 1.95(3) 2.8225(15) 167(2) 2_675 yes
O12 H12B O8 0.84(3) 1.97(3) 2.8063(16) 172(2) . yes
O13 H13A O3 0.82(3) 2.00(3) 2.7914(15) 165(2) 1_565 yes
O13 H13B O12 0.85(3) 2.00(3) 2.8432(16) 168(2) 1_655 yes
N1 H1N O3 0.92(2) 1.92(2) 2.8114(16) 162.8(18) 2_765 yes
N1 H2N O8 0.90(2) 2.09(2) 2.9249(16) 154.3(18) 1_655 yes
N1 H3N O10 0.89(2) 1.94(2) 2.7858(17) 157(2) . yes

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_compound3_Ph3EtPLH4
_database_code_depnum_ccdc_archive 'CCDC 2505720'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 P, C4 H12 N O7 P2, 4(H2 O)'
_chemical_formula_sum            'C24 H40 N O11 P3'
_chemical_formula_weight         611.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   17.3376(2)
_cell_length_b                   9.89520(10)
_cell_length_c                   18.6706(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.585(2)
_cell_angle_gamma                90
_cell_volume                     2864.45(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    20213
_cell_measurement_theta_min      5.1730
_cell_measurement_theta_max      79.3740

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    2.422
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.39307
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            30826
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.761
_diffrn_reflns_theta_max         79.630
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6122
_reflns_number_gt                5539
_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 system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_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)+(0.0487P)²+2.6271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         6122
_refine_ls_number_parameters     401
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.057
_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
P1 P 0.88172(2) 0.05483(4) 0.62878(2) 0.01312(10) Uani 1 1 d . . . . .
P2 P 0.92180(2) 0.35307(4) 0.61546(2) 0.01288(10) Uani 1 1 d . . . . .
P3 P 0.38524(3) 0.88792(5) 0.23906(3) 0.02034(11) Uani 1 1 d . . . . .
O1 O 0.78665(7) 0.11397(13) 0.59280(8) 0.0196(3) Uani 1 1 d D . . . .
O2 O 0.92327(8) 0.05422(12) 0.71939(7) 0.0186(2) Uani 1 1 d . . . . .
O3 O 0.87741(8) -0.08236(12) 0.59241(7) 0.0194(2) Uani 1 1 d . . . . .
O4 O 0.82453(8) 0.36342(12) 0.58194(8) 0.0201(3) Uani 1 1 d . . . . .
O5 O 0.96492(8) 0.36575(12) 0.70913(7) 0.0199(3) Uani 1 1 d D . . . .
O6 O 0.96248(7) 0.45309(12) 0.58146(7) 0.0159(2) Uani 1 1 d . . . . .
O7 O 1.03083(7) 0.14036(12) 0.63506(7) 0.0158(2) Uani 1 1 d D . . . .
O8 O 0.87215(8) 0.53628(14) 0.42216(8) 0.0212(3) Uani 1 1 d D . . . .
H8A H 0.8958(15) 0.504(3) 0.4685(11) 0.032 Uiso 1 1 d D U . . .
H8B H 0.9133(13) 0.551(3) 0.4090(14) 0.032 Uiso 1 1 d D U . . .
O9 O 0.79030(8) 0.75530(14) 0.45876(8) 0.0256(3) Uani 1 1 d D . . . .
H9A H 0.8199(15) 0.814(2) 0.4931(14) 0.038 Uiso 1 1 d D U . . .
H9B H 0.8257(15) 0.705(2) 0.4496(16) 0.038 Uiso 1 1 d D U . . .
O10 O 0.75485(10) 0.61014(16) 0.56762(10) 0.0335(3) Uani 1 1 d D . . . .
H10A H 0.7776(19) 0.528(2) 0.5705(18) 0.050 Uiso 1 1 d D U . . .
H10B H 0.7639(19) 0.658(3) 0.5317(15) 0.050 Uiso 1 1 d D U . . .
O11 O 0.86075(10) 0.71918(18) 0.71079(10) 0.0395(4) Uani 1 1 d D . . . .
H11A H 0.8297(19) 0.676(3) 0.6622(14) 0.059 Uiso 1 1 d D U . . .
H11B H 0.868(2) 0.803(2) 0.6967(18) 0.059 Uiso 1 1 d D U . . .
N1 N 0.99436(10) 0.27823(15) 0.35738(9) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.94145(9) 0.17596(16) 0.59549(9) 0.0122(3) Uani 1 1 d . . . . .
C2 C 0.91027(10) 0.15821(17) 0.50435(9) 0.0144(3) Uani 1 1 d . . . . .
H2A H 0.900168 0.060932 0.491042 0.017 Uiso 1 1 calc R U . . .
H2B H 0.854450 0.205572 0.475398 0.017 Uiso 1 1 calc R U . . .
C3 C 0.97340(10) 0.21183(17) 0.47466(9) 0.0150(3) Uani 1 1 d . . . . .
H3A H 0.992083 0.303940 0.496119 0.018 Uiso 1 1 calc R U . . .
H3B H 1.025118 0.153183 0.494973 0.018 Uiso 1 1 calc R U . . .
C4 C 0.93292(10) 0.21604(17) 0.38383(9) 0.0161(3) Uani 1 1 d . . . . .
H4A H 0.918310 0.123212 0.362144 0.019 Uiso 1 1 calc R U . . .
H4B H 0.879020 0.269599 0.362980 0.019 Uiso 1 1 calc R U . . .
C5 C 0.32683(11) 0.73342(19) 0.23000(10) 0.0205(3) Uani 1 1 d . . . . .
C6 C 0.31938(11) 0.63664(19) 0.17301(11) 0.0214(4) Uani 1 1 d . . . . .
H6 H 0.343433 0.653454 0.137059 0.026 Uiso 1 1 calc R U . . .
C7 C 0.27673(11) 0.5152(2) 0.16866(11) 0.0244(4) Uani 1 1 d . . . . .
H7 H 0.272218 0.448802 0.130246 0.029 Uiso 1 1 calc R U . . .
C8 C 0.24088(11) 0.4920(2) 0.22074(12) 0.0265(4) Uani 1 1 d . . . . .
H8 H 0.211281 0.409720 0.217624 0.032 Uiso 1 1 calc R U . . .
C9 C 0.24814(12) 0.5888(2) 0.27758(12) 0.0283(4) Uani 1 1 d . . . . .
H9 H 0.223355 0.572243 0.312974 0.034 Uiso 1 1 calc R U . . .
C10 C 0.29118(12) 0.7089(2) 0.28286(11) 0.0256(4) Uani 1 1 d . . . . .
H10 H 0.296520 0.774298 0.322064 0.031 Uiso 1 1 calc R U . . .
C11 C 0.42667(13) 0.88676(19) 0.16611(12) 0.0246(4) Uani 1 1 d . . . . .
C12 C 0.36832(14) 0.8899(2) 0.08451(13) 0.0314(4) Uani 1 1 d . . . . .
H12 H 0.308115 0.897092 0.068138 0.038 Uiso 1 1 calc R U . . .
C13 C 0.39949(17) 0.8822(2) 0.02806(14) 0.0377(5) Uani 1 1 d . . . . .
H13 H 0.360328 0.883899 -0.027344 0.045 Uiso 1 1 calc R U . . .
C14 C 0.48692(18) 0.8723(2) 0.05157(15) 0.0392(5) Uani 1 1 d . . . . .
H14 H 0.507361 0.864448 0.012277 0.047 Uiso 1 1 calc R U . . .
C15 C 0.54503(16) 0.8736(2) 0.13200(15) 0.0367(5) Uani 1 1 d . . . . .
H15 H 0.605235 0.869789 0.147760 0.044 Uiso 1 1 calc R U . . .
C16 C 0.51503(13) 0.88047(19) 0.18981(13) 0.0279(4) Uani 1 1 d . . . . .
H16 H 0.554640 0.880883 0.245088 0.033 Uiso 1 1 calc R U . . .
C17 C 0.47442(11) 0.88969(18) 0.33740(11) 0.0203(3) Uani 1 1 d . . . . .
C18 C 0.51769(12) 0.76815(19) 0.36748(12) 0.0253(4) Uani 1 1 d . . . . .
H18 H 0.495649 0.686193 0.339166 0.030 Uiso 1 1 calc R U . . .
C19 C 0.59295(12) 0.7675(2) 0.43883(13) 0.0302(4) Uani 1 1 d . . . . .
H19 H 0.623169 0.685134 0.458841 0.036 Uiso 1 1 calc R U . . .
C20 C 0.62427(12) 0.8866(2) 0.48110(11) 0.0261(4) Uani 1 1 d . . . . .
H20 H 0.675918 0.885731 0.529935 0.031 Uiso 1 1 calc R U . . .
C21 C 0.58056(13) 1.0062(2) 0.45235(12) 0.0283(4) Uani 1 1 d . . . . .
H21 H 0.601372 1.087157 0.482215 0.034 Uiso 1 1 calc R U . . .
C22 C 0.50602(12) 1.0091(2) 0.37972(12) 0.0267(4) Uani 1 1 d . . . . .
H22 H 0.476971 1.092139 0.359235 0.032 Uiso 1 1 calc R U . . .
C23 C 0.32066(13) 1.0382(2) 0.22050(13) 0.0301(4) Uani 1 1 d . . . . .
H23A H 0.357901 1.117501 0.226450 0.036 Uiso 1 1 calc R U . . .
H23B H 0.275649 1.036250 0.164203 0.036 Uiso 1 1 calc R U . . .
C24 C 0.27692(16) 1.0585(3) 0.27421(16) 0.0408(5) Uani 1 1 d . . . . .
H24A H 0.249719 1.147911 0.264176 0.061 Uiso 1 1 calc R U . . .
H24B H 0.319920 1.052156 0.330402 0.061 Uiso 1 1 calc R U . . .
H24C H 0.232881 0.988696 0.262745 0.061 Uiso 1 1 calc R U . . .
H1 H 0.7923(17) 0.1977(18) 0.5908(17) 0.039(7) Uiso 1 1 d D . . . .
H5 H 1.0012(16) 0.429(2) 0.7286(17) 0.044(8) Uiso 1 1 d D . . . .
H7A H 1.0527(16) 0.163(3) 0.6834(11) 0.038(7) Uiso 1 1 d D . . . .
H1N H 0.9703(16) 0.293(3) 0.3064(16) 0.030(6) Uiso 1 1 d . . . . .
H2N H 1.0400(16) 0.224(3) 0.3710(15) 0.029(6) Uiso 1 1 d . . . . .
H3N H 1.0112(16) 0.360(3) 0.3830(15) 0.029(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
P1 O3 1.5047(13) . ?
P1 O2 1.5133(12) . ?
P1 O1 1.5873(12) . ?
P1 C1 1.8634(16) . ?
P2 O6 1.5101(12) . ?
P2 O4 1.5171(12) . ?
P2 O5 1.5695(12) . ?
P2 C1 1.8548(16) . ?
P3 C17 1.7947(18) . ?
P3 C5 1.7995(19) . ?
P3 C23 1.800(2) . ?
P3 C11 1.802(2) . ?
O7 C1 1.4305(18) . ?
N1 C4 1.493(2) . ?
C1 C2 1.548(2) . ?
C2 C3 1.527(2) . ?
C3 C4 1.518(2) . ?
C5 C6 1.394(3) . ?
C5 C10 1.400(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.393(3) . ?
C9 C10 1.383(3) . ?
C11 C16 1.393(3) . ?
C11 C12 1.402(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.380(4) . ?
C14 C15 1.384(4) . ?
C15 C16 1.394(3) . ?
C17 C22 1.390(3) . ?
C17 C18 1.396(3) . ?
C18 C19 1.386(3) . ?
C19 C20 1.387(3) . ?
C20 C21 1.378(3) . ?
C21 C22 1.393(3) . ?
C23 C24 1.517(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
O3 P1 O2 113.80(7) . . ?
O3 P1 O1 108.01(7) . . ?
O2 P1 O1 111.06(7) . . ?
O3 P1 C1 110.64(7) . . ?
O2 P1 C1 108.53(7) . . ?
O1 P1 C1 104.39(7) . . ?
O6 P2 O4 115.12(7) . . ?
O6 P2 O5 109.69(7) . . ?
O4 P2 O5 109.96(7) . . ?
O6 P2 C1 111.87(7) . . ?
O4 P2 C1 104.55(7) . . ?
O5 P2 C1 105.12(7) . . ?
C17 P3 C5 107.18(8) . . ?
C17 P3 C23 111.45(9) . . ?
C5 P3 C23 114.12(9) . . ?
C17 P3 C11 108.73(9) . . ?
C5 P3 C11 108.75(8) . . ?
C23 P3 C11 106.49(10) . . ?
O7 C1 C2 107.73(12) . . ?
O7 C1 P2 112.51(10) . . ?
C2 C1 P2 108.84(10) . . ?
O7 C1 P1 107.74(10) . . ?
C2 C1 P1 108.72(10) . . ?
P2 C1 P1 111.18(8) . . ?
C3 C2 C1 113.92(13) . . ?
C4 C3 C2 111.53(13) . . ?
N1 C4 C3 109.83(13) . . ?
C6 C5 C10 119.98(17) . . ?
C6 C5 P3 120.75(14) . . ?
C10 C5 P3 119.23(15) . . ?
C7 C6 C5 120.13(17) . . ?
C8 C7 C6 119.64(18) . . ?
C7 C8 C9 120.23(18) . . ?
C10 C9 C8 120.48(17) . . ?
C9 C10 C5 119.53(18) . . ?
C16 C11 C12 120.16(19) . . ?
C16 C11 P3 120.93(15) . . ?
C12 C11 P3 118.90(16) . . ?
C13 C12 C11 119.2(2) . . ?
C14 C13 C12 120.6(2) . . ?
C13 C14 C15 120.5(2) . . ?
C14 C15 C16 119.9(2) . . ?
C11 C16 C15 119.7(2) . . ?
C22 C17 C18 119.97(16) . . ?
C22 C17 P3 121.98(14) . . ?
C18 C17 P3 117.72(14) . . ?
C19 C18 C17 119.76(18) . . ?
C18 C19 C20 120.20(18) . . ?
C21 C20 C19 120.09(17) . . ?
C20 C21 C22 120.37(18) . . ?
C17 C22 C21 119.58(18) . . ?
C24 C23 P3 115.73(16) . . ?

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
O6 P2 C1 O7 64.74(12) . . . . ?
O4 P2 C1 O7 -170.04(10) . . . . ?
O5 P2 C1 O7 -54.23(12) . . . . ?
O6 P2 C1 C2 -54.59(11) . . . . ?
O4 P2 C1 C2 70.63(11) . . . . ?
O5 P2 C1 C2 -173.56(10) . . . . ?
O6 P2 C1 P1 -174.32(7) . . . . ?
O4 P2 C1 P1 -49.10(9) . . . . ?
O5 P2 C1 P1 66.71(9) . . . . ?
O3 P1 C1 O7 -72.16(11) . . . . ?
O2 P1 C1 O7 53.36(12) . . . . ?
O1 P1 C1 O7 171.87(10) . . . . ?
O3 P1 C1 C2 44.32(12) . . . . ?
O2 P1 C1 C2 169.85(10) . . . . ?
O1 P1 C1 C2 -71.64(11) . . . . ?
O3 P1 C1 P2 164.12(7) . . . . ?
O2 P1 C1 P2 -70.35(9) . . . . ?
O1 P1 C1 P2 48.16(9) . . . . ?
O7 C1 C2 C3 -42.94(18) . . . . ?
P2 C1 C2 C3 79.33(14) . . . . ?
P1 C1 C2 C3 -159.43(11) . . . . ?
C1 C2 C3 C4 -169.33(13) . . . . ?
C2 C3 C4 N1 175.91(13) . . . . ?
C17 P3 C5 C6 -117.55(15) . . . . ?
C23 P3 C5 C6 118.55(16) . . . . ?
C11 P3 C5 C6 -0.17(17) . . . . ?
C17 P3 C5 C10 60.25(16) . . . . ?
C23 P3 C5 C10 -63.66(17) . . . . ?
C11 P3 C5 C10 177.63(14) . . . . ?
C10 C5 C6 C7 -0.2(3) . . . . ?
P3 C5 C6 C7 177.59(14) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C5 0.7(3) . . . . ?
C6 C5 C10 C9 -0.5(3) . . . . ?
P3 C5 C10 C9 -178.32(14) . . . . ?
C17 P3 C11 C16 3.23(18) . . . . ?
C5 P3 C11 C16 -113.16(16) . . . . ?
C23 P3 C11 C16 123.44(16) . . . . ?
C17 P3 C11 C12 -177.90(15) . . . . ?
C5 P3 C11 C12 65.71(17) . . . . ?
C23 P3 C11 C12 -57.69(17) . . . . ?
C16 C11 C12 C13 2.0(3) . . . . ?
P3 C11 C12 C13 -176.83(16) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 -1.8(3) . . . . ?
C13 C14 C15 C16 2.1(3) . . . . ?
C12 C11 C16 C15 -1.7(3) . . . . ?
P3 C11 C16 C15 177.12(15) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C5 P3 C17 C22 -147.19(16) . . . . ?
C23 P3 C17 C22 -21.7(2) . . . . ?
C11 P3 C17 C22 95.41(17) . . . . ?
C5 P3 C17 C18 39.45(17) . . . . ?
C23 P3 C17 C18 164.97(15) . . . . ?
C11 P3 C17 C18 -77.95(17) . . . . ?
C22 C17 C18 C19 -1.1(3) . . . . ?
P3 C17 C18 C19 172.37(16) . . . . ?
C17 C18 C19 C20 1.3(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 -1.7(3) . . . . ?
C18 C17 C22 C21 -0.5(3) . . . . ?
P3 C17 C22 C21 -173.68(16) . . . . ?
C20 C21 C22 C17 1.9(3) . . . . ?
C17 P3 C23 C24 -63.07(19) . . . . ?
C5 P3 C23 C24 58.51(19) . . . . ?
C11 P3 C23 C24 178.50(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O8 H8A O6 0.838(16) 1.963(17) 2.7941(17) 171(3) . yes
O8 H8B O6 0.864(16) 2.080(18) 2.8999(17) 158(2) 3_766 yes
O9 H9A O3 0.850(17) 1.955(18) 2.7776(19) 163(3) 1_565 yes
O9 H9B O8 0.864(16) 2.018(18) 2.8365(19) 158(2) . yes
O10 H10A O4 0.897(17) 1.788(17) 2.6836(19) 177(3) . yes
O10 H10B O9 0.889(17) 1.885(18) 2.773(2) 176(3) . yes
O11 H11A O10 0.927(17) 1.782(19) 2.700(2) 170(3) . yes
O11 H11B O2 0.894(18) 2.63(2) 3.469(2) 156(3) 1_565 yes
O11 H11B O3 0.894(18) 2.32(3) 3.0654(19) 141(3) 1_565 yes
O1 H1 O4 0.837(17) 1.764(18) 2.5855(18) 167(3) . yes
O5 H5 O2 0.848(18) 1.746(18) 2.5886(18) 173(3) 2_756 yes
O7 H7A O11 0.839(17) 1.951(18) 2.7537(19) 160(3) 2_746 yes
N1 H1N O2 0.86(3) 2.10(3) 2.8396(19) 144(2) 4_565 yes
N1 H1N O5 0.86(3) 2.37(3) 2.9473(19) 124(2) 4_565 yes
N1 H2N O3 0.89(3) 1.90(3) 2.777(2) 167(2) 3_756 yes
N1 H3N O6 0.92(3) 1.95(3) 2.8579(19) 170(2) 3_766 yes

_refine_diff_density_max         0.836
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_compound2_Ph3PMeLH4
_database_code_depnum_ccdc_archive 'CCDC 2505722'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C19
_chemical_formula_sum            'C23 H30 N O7 P3'
_chemical_formula_weight         525.39

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'
N N 0.0311 0.0180 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.8268(2)
_cell_length_b                   9.20120(10)
_cell_length_c                   18.5019(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.2040(10)
_cell_angle_gamma                90
_cell_volume                     2423.84(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    17413
_cell_measurement_theta_min      5.0260
_cell_measurement_theta_max      77.1840

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    2.645
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.68063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            26595
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.978
_diffrn_reflns_theta_max         77.499
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5084
_reflns_number_gt                4661
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELX2-2018/3 (Sheldrick, 2018)'
_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)+(0.0451P)²+1.1811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         5084
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
P1 P 0.08768(3) 0.86081(4) 0.67790(2) 0.01798(10) Uani 1 1 d . . . . .
P2 P 0.15597(2) 0.54568(4) 0.71593(2) 0.01666(10) Uani 1 1 d . . . . .
P3 P 0.29281(2) 0.10638(4) 0.51587(2) 0.01656(10) Uani 1 1 d . . . . .
O1 O 0.19804(9) 0.88415(14) 0.70727(7) 0.0289(3) Uani 1 1 d . . . . .
O2 O 0.04244(8) 0.87098(12) 0.74139(6) 0.0240(2) Uani 1 1 d . . . . .
O3 O 0.04900(9) 0.96496(12) 0.61462(6) 0.0274(3) Uani 1 1 d . . . . .
O4 O 0.24927(8) 0.61958(13) 0.74696(6) 0.0253(3) Uani 1 1 d . . . . .
O5 O 0.10543(8) 0.53846(12) 0.78106(6) 0.0212(2) Uani 1 1 d . . . . .
O6 O 0.15468(7) 0.40028(12) 0.67936(6) 0.0202(2) Uani 1 1 d . . . . .
O7 O -0.01640(7) 0.62072(12) 0.62935(6) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.00856(9) 0.75840(15) 0.36552(7) 0.0182(3) Uani 1 1 d . . . . .
C1 C 0.07982(9) 0.66991(16) 0.64513(8) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.10955(10) 0.65725(16) 0.57224(8) 0.0166(3) Uani 1 1 d . . . . .
H2A H 0.168633 0.712352 0.578742 0.020 Uiso 1 1 calc R U . . .
H2B H 0.123234 0.553907 0.564775 0.020 Uiso 1 1 calc R U . . .
C3 C 0.03798(10) 0.71171(16) 0.50119(8) 0.0169(3) Uani 1 1 d . . . . .
H3A H -0.018746 0.649576 0.490175 0.020 Uiso 1 1 calc R U . . .
H3B H 0.019077 0.812234 0.509313 0.020 Uiso 1 1 calc R U . . .
C4 C 0.07919(10) 0.70881(17) 0.43492(8) 0.0179(3) Uani 1 1 d . . . . .
H4A H 0.134976 0.772907 0.445365 0.021 Uiso 1 1 calc R U . . .
H4B H 0.099525 0.608750 0.427538 0.021 Uiso 1 1 calc R U . . .
C5 C 0.17378(11) 0.11792(19) 0.51911(11) 0.0269(4) Uani 1 1 d . . . . .
H5A H 0.132242 0.077339 0.472718 0.040 Uiso 1 1 calc R U . . .
H5B H 0.157340 0.219919 0.523945 0.040 Uiso 1 1 calc R U . . .
H5C H 0.166425 0.062835 0.562444 0.040 Uiso 1 1 calc R U . . .
C6 C 0.36967(10) 0.17988(16) 0.60074(8) 0.0172(3) Uani 1 1 d . . . . .
C7 C 0.33602(11) 0.28934(17) 0.63876(9) 0.0216(3) Uani 1 1 d . . . . .
H7 H 0.271874 0.317493 0.622508 0.026 Uiso 1 1 calc R U . . .
C8 C 0.39691(13) 0.35649(18) 0.70035(9) 0.0261(3) Uani 1 1 d . . . . .
H8 H 0.374457 0.430721 0.726554 0.031 Uiso 1 1 calc R U . . .
C9 C 0.49078(12) 0.31535(19) 0.72380(9) 0.0260(3) Uani 1 1 d . . . . .
H9 H 0.532403 0.363510 0.765307 0.031 Uiso 1 1 calc R U . . .
C10 C 0.52454(11) 0.20484(19) 0.68738(9) 0.0238(3) Uani 1 1 d . . . . .
H10 H 0.588506 0.175984 0.704491 0.029 Uiso 1 1 calc R U . . .
C11 C 0.46370(10) 0.13657(17) 0.62546(9) 0.0198(3) Uani 1 1 d . . . . .
H11 H 0.486072 0.060806 0.600125 0.024 Uiso 1 1 calc R U . . .
C12 C 0.32054(10) -0.08103(17) 0.50691(9) 0.0181(3) Uani 1 1 d . . . . .
C13 C 0.33284(10) -0.17142(18) 0.56981(9) 0.0217(3) Uani 1 1 d . . . . .
H13 H 0.333215 -0.131310 0.617203 0.026 Uiso 1 1 calc R U . . .
C14 C 0.34444(11) -0.31940(19) 0.56262(11) 0.0275(4) Uani 1 1 d . . . . .
H14 H 0.353086 -0.381186 0.605147 0.033 Uiso 1 1 calc R U . . .
C15 C 0.34341(12) -0.37743(18) 0.49310(12) 0.0315(4) Uani 1 1 d . . . . .
H15 H 0.351702 -0.478997 0.488300 0.038 Uiso 1 1 calc R U . . .
C16 C 0.33036(13) -0.28806(19) 0.43062(11) 0.0301(4) Uani 1 1 d . . . . .
H16 H 0.329233 -0.328886 0.383215 0.036 Uiso 1 1 calc R U . . .
C17 C 0.31894(11) -0.13953(18) 0.43700(9) 0.0226(3) Uani 1 1 d . . . . .
H17 H 0.310139 -0.078276 0.394257 0.027 Uiso 1 1 calc R U . . .
C18 C 0.30704(10) 0.20855(16) 0.43728(8) 0.0187(3) Uani 1 1 d . . . . .
C19 C 0.39641(11) 0.24761(19) 0.43349(9) 0.0248(3) Uani 1 1 d . . . . .
H19 H 0.450457 0.217610 0.471726 0.030 Uiso 1 1 calc R U . . .
C20 C 0.40580(12) 0.3305(2) 0.37355(10) 0.0294(4) Uani 1 1 d . . . . .
H20 H 0.466568 0.357615 0.370779 0.035 Uiso 1 1 calc R U . . .
C21 C 0.32702(13) 0.37416(18) 0.31752(9) 0.0262(3) Uani 1 1 d . . . . .
H21 H 0.333983 0.431951 0.276867 0.031 Uiso 1 1 calc R U . . .
C22 C 0.23895(13) 0.3340(2) 0.32071(10) 0.0330(4) Uani 1 1 d . . . . .
H22 H 0.185196 0.363339 0.281995 0.040 Uiso 1 1 calc R U . . .
C23 C 0.22827(12) 0.2506(2) 0.38040(10) 0.0302(4) Uani 1 1 d . . . . .
H23 H 0.167365 0.222373 0.382355 0.036 Uiso 1 1 calc R U . . .
H1 H 0.2218(17) 0.805(3) 0.7285(14) 0.043(7) Uiso 1 1 d . . . . .
H5 H 0.057(2) 0.472(3) 0.7723(16) 0.061(8) Uiso 1 1 d . . . . .
H7A H -0.0269(17) 0.615(3) 0.6689(14) 0.038(6) Uiso 1 1 d . . . . .
H3N H -0.0083(15) 0.853(3) 0.3692(12) 0.035(6) Uiso 1 1 d . . . . .
H1N H 0.0299(15) 0.750(2) 0.3244(13) 0.031(5) Uiso 1 1 d . . . . .
H2N H -0.0485(15) 0.698(2) 0.3559(11) 0.029(5) 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
P1 O3 1.4977(12) . ?
P1 O2 1.5094(11) . ?
P1 O1 1.5883(13) . ?
P1 C1 1.8513(15) . ?
P2 O6 1.4970(11) . ?
P2 O4 1.5042(11) . ?
P2 O5 1.5880(11) . ?
P2 C1 1.8633(15) . ?
P3 C5 1.7857(16) . ?
P3 C12 1.7911(16) . ?
P3 C18 1.7927(16) . ?
P3 C6 1.7952(15) . ?
O1 H1 0.86(3) . ?
O5 H5 0.92(3) . ?
O7 C1 1.4467(17) . ?
O7 H7A 0.79(3) . ?
N1 C4 1.4843(19) . ?
N1 H3N 0.91(2) . ?
N1 H1N 0.90(2) . ?
N1 H2N 0.99(2) . ?
C1 C2 1.5356(19) . ?
C2 C3 1.5254(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5152(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.398(2) . ?
C6 C11 1.399(2) . ?
C7 C8 1.386(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.395(2) . ?
C12 C13 1.400(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.391(2) . ?
C18 C19 1.393(2) . ?
C19 C20 1.385(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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
O3 P1 O2 114.36(7) . . ?
O3 P1 O1 108.31(8) . . ?
O2 P1 O1 111.38(7) . . ?
O3 P1 C1 112.06(7) . . ?
O2 P1 C1 108.22(7) . . ?
O1 P1 C1 101.83(7) . . ?
O6 P2 O4 118.09(7) . . ?
O6 P2 O5 110.88(6) . . ?
O4 P2 O5 107.92(6) . . ?
O6 P2 C1 107.56(6) . . ?
O4 P2 C1 107.66(7) . . ?
O5 P2 C1 103.74(6) . . ?
C5 P3 C12 108.36(7) . . ?
C5 P3 C18 109.70(8) . . ?
C12 P3 C18 110.36(7) . . ?
C5 P3 C6 109.90(8) . . ?
C12 P3 C6 109.73(7) . . ?
C18 P3 C6 108.79(7) . . ?
P1 O1 H1 107.2(17) . . ?
P2 O5 H5 113.6(17) . . ?
C1 O7 H7A 105.8(17) . . ?
C4 N1 H3N 111.7(14) . . ?
C4 N1 H1N 111.9(14) . . ?
H3N N1 H1N 108.3(19) . . ?
C4 N1 H2N 110.2(12) . . ?
H3N N1 H2N 108.3(18) . . ?
H1N N1 H2N 106.3(18) . . ?
O7 C1 C2 107.92(11) . . ?
O7 C1 P1 109.35(9) . . ?
C2 C1 P1 110.63(10) . . ?
O7 C1 P2 108.65(10) . . ?
C2 C1 P2 107.74(9) . . ?
P1 C1 P2 112.42(7) . . ?
C3 C2 C1 115.51(12) . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C2 110.55(12) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C3 110.38(12) . . ?
N1 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
P3 C5 H5A 109.5 . . ?
P3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
P3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 120.26(14) . . ?
C7 C6 P3 118.88(11) . . ?
C11 C6 P3 120.68(12) . . ?
C8 C7 C6 119.53(15) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.07(15) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.89(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.38(15) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C6 119.85(15) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
C17 C12 C13 120.39(15) . . ?
C17 C12 P3 120.82(12) . . ?
C13 C12 P3 118.36(12) . . ?
C14 C13 C12 119.71(16) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.86(16) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.45(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.35(17) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 119.24(16) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
C23 C18 C19 119.97(15) . . ?
C23 C18 P3 119.70(13) . . ?
C19 C18 P3 120.33(11) . . ?
C20 C19 C18 119.47(15) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.41(16) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.13(16) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.19(16) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 119.81(16) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?

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
O3 P1 C1 O7 -75.23(11) . . . . ?
O2 P1 C1 O7 51.77(11) . . . . ?
O1 P1 C1 O7 169.23(10) . . . . ?
O3 P1 C1 C2 43.50(12) . . . . ?
O2 P1 C1 C2 170.50(9) . . . . ?
O1 P1 C1 C2 -72.04(11) . . . . ?
O3 P1 C1 P2 164.00(8) . . . . ?
O2 P1 C1 P2 -68.99(9) . . . . ?
O1 P1 C1 P2 48.46(9) . . . . ?
O6 P2 C1 O7 66.88(11) . . . . ?
O4 P2 C1 O7 -164.88(9) . . . . ?
O5 P2 C1 O7 -50.65(11) . . . . ?
O6 P2 C1 C2 -49.80(11) . . . . ?
O4 P2 C1 C2 78.44(11) . . . . ?
O5 P2 C1 C2 -167.34(9) . . . . ?
O6 P2 C1 P1 -171.95(7) . . . . ?
O4 P2 C1 P1 -43.71(9) . . . . ?
O5 P2 C1 P1 70.51(8) . . . . ?
O7 C1 C2 C3 44.42(16) . . . . ?
P1 C1 C2 C3 -75.18(13) . . . . ?
P2 C1 C2 C3 161.57(10) . . . . ?
C1 C2 C3 C4 173.87(12) . . . . ?
C2 C3 C4 N1 178.60(12) . . . . ?
C5 P3 C6 C7 -29.15(15) . . . . ?
C12 P3 C6 C7 -148.20(12) . . . . ?
C18 P3 C6 C7 90.97(13) . . . . ?
C5 P3 C6 C11 155.64(13) . . . . ?
C12 P3 C6 C11 36.59(14) . . . . ?
C18 P3 C6 C11 -84.23(14) . . . . ?
C11 C6 C7 C8 1.2(2) . . . . ?
P3 C6 C7 C8 -174.07(12) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C8 C9 C10 C11 1.4(2) . . . . ?
C9 C10 C11 C6 0.0(2) . . . . ?
C7 C6 C11 C10 -1.3(2) . . . . ?
P3 C6 C11 C10 173.87(12) . . . . ?
C5 P3 C12 C17 99.29(14) . . . . ?
C18 P3 C12 C17 -20.85(14) . . . . ?
C6 P3 C12 C17 -140.72(12) . . . . ?
C5 P3 C12 C13 -73.20(13) . . . . ?
C18 P3 C12 C13 166.67(11) . . . . ?
C6 P3 C12 C13 46.80(13) . . . . ?
C17 C12 C13 C14 0.7(2) . . . . ?
P3 C12 C13 C14 173.19(12) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C13 C12 C17 C16 -0.5(2) . . . . ?
P3 C12 C17 C16 -172.80(12) . . . . ?
C5 P3 C18 C23 -15.73(16) . . . . ?
C12 P3 C18 C23 103.59(14) . . . . ?
C6 P3 C18 C23 -135.98(14) . . . . ?
C5 P3 C18 C19 163.39(13) . . . . ?
C12 P3 C18 C19 -77.29(14) . . . . ?
C6 P3 C18 C19 43.15(15) . . . . ?
C23 C18 C19 C20 1.2(3) . . . . ?
P3 C18 C19 C20 -177.95(14) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C22 C23 C18 0.4(3) . . . . ?
C19 C18 C23 C22 -1.3(3) . . . . ?
P3 C18 C23 C22 177.83(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.86(3) 1.77(3) 2.5944(18) 163(2) . yes
O5 H5 O2 0.92(3) 1.70(3) 2.6166(16) 171(3) 2_546 yes
O7 H7A O5 0.79(3) 2.53(2) 2.9807(15) 118(2) . yes
N1 H3N O3 0.91(2) 1.83(2) 2.7418(18) 173(2) 3_576 yes
N1 H1N O2 0.90(2) 1.95(2) 2.7545(17) 148(2) 4_575 yes
N1 H2N O6 0.99(2) 1.77(2) 2.7492(17) 169.2(18) 3_566 yes

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_compound1b_Ph4PLH4LH5
_database_code_depnum_ccdc_archive 'CCDC 2505723'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C24 H20 P, C4 H13 N O7 P2, C4 H12 N O7 P2, C2 H6 O, H2 O'
_chemical_formula_sum            'C34 H53 N2 O16 P5'
_chemical_formula_weight         900.63

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'
N N 0.0311 0.0180 '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                   9.51850(10)
_cell_length_b                   13.6577(2)
_cell_length_c                   17.1463(2)
_cell_angle_alpha                82.1570(10)
_cell_angle_beta                 74.6060(10)
_cell_angle_gamma                76.5750(10)
_cell_volume                     2083.67(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    17370
_cell_measurement_theta_min      4.4370
_cell_measurement_theta_max      79.1280

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.659
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.85134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            31516
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.113
_diffrn_reflns_theta_max         79.997
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8876
_reflns_number_gt                7920
_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 system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0509P)²+0.7349P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         8876
_refine_ls_number_parameters     579
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
P1 P 0.70441(4) 0.14950(3) 0.43654(2) 0.01248(9) Uani 1 1 d . . . . .
P2 P 0.50122(4) 0.24568(2) 0.58789(2) 0.01134(8) Uani 1 1 d . . . . .
P3 P 0.30690(4) 0.27348(3) 0.30330(2) 0.01605(9) Uani 1 1 d . . . . .
P4 P 0.40639(4) 0.45737(3) 0.33247(2) 0.01404(9) Uani 1 1 d . . . . .
P5 P 0.06449(4) 0.20111(3) 0.91037(2) 0.01476(9) Uani 1 1 d . . . . .
O1 O 0.73654(12) 0.24934(8) 0.38638(6) 0.0166(2) Uani 1 1 d . . . . .
O2 O 0.55347(13) 0.13017(9) 0.43389(7) 0.0209(2) Uani 1 1 d D . . . .
O3 O 0.83117(12) 0.06342(8) 0.41073(7) 0.0173(2) Uani 1 1 d . . . . .
O4 O 0.47081(12) 0.33087(8) 0.52489(6) 0.0157(2) Uani 1 1 d . . . . .
O5 O 0.39420(12) 0.17602(8) 0.61829(6) 0.0169(2) Uani 1 1 d . . . . .
O6 O 0.52120(12) 0.28931(8) 0.66406(6) 0.0148(2) Uani 1 1 d . . . . .
O7 O 0.68519(12) 0.06392(8) 0.58514(7) 0.0165(2) Uani 1 1 d . . . . .
O8 O 0.38889(15) 0.18138(9) 0.34514(9) 0.0294(3) Uani 1 1 d . . . . .
O9 O 0.15438(14) 0.24932(9) 0.30251(8) 0.0229(2) Uani 1 1 d . . . . .
O10 O 0.38488(16) 0.30755(10) 0.21931(8) 0.0315(3) Uani 1 1 d . . . . .
O11 O 0.55201(13) 0.39282(8) 0.34204(7) 0.0210(2) Uani 1 1 d . . . . .
O12 O 0.35868(13) 0.55202(8) 0.37696(7) 0.0204(2) Uani 1 1 d . . . . .
O13 O 0.40810(13) 0.48955(9) 0.24005(7) 0.0211(2) Uani 1 1 d . . . . .
O14 O 0.24489(13) 0.34867(8) 0.45017(6) 0.0179(2) Uani 1 1 d . . . . .
O15 O 0.11741(14) 0.06624(9) 0.32808(7) 0.0202(2) Uani 1 1 d . . . . .
O16 O 0.3991(3) 0.26033(13) 0.06620(11) 0.0527(5) Uani 1 1 d . . . . .
N1 N 1.22985(14) 0.12774(10) 0.52869(9) 0.0168(3) Uani 1 1 d . . . . .
N2 N -0.30914(15) 0.48052(10) 0.44985(9) 0.0188(3) Uani 1 1 d . . . . .
C1 C 0.68325(16) 0.16488(10) 0.54454(8) 0.0124(3) Uani 1 1 d . . . . .
C2 C 0.80883(16) 0.20571(10) 0.56101(9) 0.0136(3) Uani 1 1 d . . . . .
H2A H 0.796955 0.277946 0.541026 0.016 Uiso 1 1 calc R U . . .
H2B H 0.795818 0.202041 0.620497 0.016 Uiso 1 1 calc R U . . .
C3 C 0.96747(16) 0.15282(10) 0.52354(9) 0.0140(3) Uani 1 1 d . . . . .
H3A H 0.974580 0.078820 0.529848 0.017 Uiso 1 1 calc R U . . .
H3B H 0.994061 0.173907 0.464822 0.017 Uiso 1 1 calc R U . . .
C4 C 1.07512(16) 0.17936(11) 0.56469(9) 0.0157(3) Uani 1 1 d . . . . .
H4A H 1.068143 0.253355 0.558203 0.019 Uiso 1 1 calc R U . . .
H4B H 1.048113 0.158572 0.623448 0.019 Uiso 1 1 calc R U . . .
C5 C 0.25892(16) 0.38256(10) 0.36616(9) 0.0137(3) Uani 1 1 d . . . . .
C6 C 0.11023(16) 0.45286(11) 0.35739(9) 0.0158(3) Uani 1 1 d . . . . .
H6A H 0.109924 0.521087 0.370962 0.019 Uiso 1 1 calc R U . . .
H6B H 0.106363 0.458300 0.299791 0.019 Uiso 1 1 calc R U . . .
C7 C -0.03139(17) 0.42026(11) 0.40981(10) 0.0195(3) Uani 1 1 d . . . . .
H7A H -0.039745 0.355733 0.392999 0.023 Uiso 1 1 calc R U . . .
H7B H -0.027454 0.410104 0.467536 0.023 Uiso 1 1 calc R U . . .
C8 C -0.16416(18) 0.50165(12) 0.39927(10) 0.0202(3) Uani 1 1 d . . . . .
H8A H -0.150986 0.566361 0.413282 0.024 Uiso 1 1 calc R U . . .
H8B H -0.167345 0.509790 0.341457 0.024 Uiso 1 1 calc R U . . .
C9 C 0.22628(18) 0.10303(11) 0.88303(9) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.2990(2) 0.04700(12) 0.94081(10) 0.0226(3) Uani 1 1 d . . . . .
H10 H 0.262563 0.059776 0.996449 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4249(2) -0.02753(13) 0.91620(13) 0.0294(4) Uani 1 1 d . . . . .
H11 H 0.475017 -0.065654 0.955090 0.035 Uiso 1 1 calc R U . . .
C12 C 0.4775(2) -0.04634(13) 0.83494(13) 0.0306(4) Uani 1 1 d . . . . .
H12 H 0.563513 -0.097413 0.818563 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4057(2) 0.00865(13) 0.77746(11) 0.0296(4) Uani 1 1 d . . . . .
H13 H 0.442450 -0.004814 0.721976 0.035 Uiso 1 1 calc R U . . .
C14 C 0.2799(2) 0.08345(12) 0.80103(10) 0.0249(3) Uani 1 1 d . . . . .
H14 H 0.230365 0.121214 0.761769 0.030 Uiso 1 1 calc R U . . .
C15 C 0.10966(18) 0.32313(11) 0.87797(9) 0.0181(3) Uani 1 1 d . . . . .
C16 C 0.2398(2) 0.33384(12) 0.81994(10) 0.0231(3) Uani 1 1 d . . . . .
H16 H 0.307898 0.276232 0.797295 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2690(2) 0.43006(14) 0.79551(11) 0.0286(4) Uani 1 1 d . . . . .
H17 H 0.358440 0.437911 0.756588 0.034 Uiso 1 1 calc R U . . .
C18 C 0.1697(2) 0.51405(13) 0.82717(11) 0.0303(4) Uani 1 1 d . . . . .
H18 H 0.190811 0.579333 0.809941 0.036 Uiso 1 1 calc R U . . .
C19 C 0.0388(2) 0.50351(13) 0.88414(11) 0.0306(4) Uani 1 1 d . . . . .
H19 H -0.030272 0.561605 0.905228 0.037 Uiso 1 1 calc R U . . .
C20 C 0.0089(2) 0.40810(13) 0.91031(10) 0.0253(3) Uani 1 1 d . . . . .
H20 H -0.079705 0.400602 0.950058 0.030 Uiso 1 1 calc R U . . .
C21 C -0.07357(18) 0.18373(11) 0.86284(9) 0.0182(3) Uani 1 1 d . . . . .
C22 C -0.1639(2) 0.26582(12) 0.83038(10) 0.0237(3) Uani 1 1 d . . . . .
H22 H -0.148968 0.332274 0.830145 0.028 Uiso 1 1 calc R U . . .
C23 C -0.2756(2) 0.25024(14) 0.79843(11) 0.0288(4) Uani 1 1 d . . . . .
H23 H -0.337928 0.306218 0.776803 0.035 Uiso 1 1 calc R U . . .
C24 C -0.2968(2) 0.15334(14) 0.79793(11) 0.0273(4) Uani 1 1 d . . . . .
H24 H -0.373321 0.143050 0.775849 0.033 Uiso 1 1 calc R U . . .
C25 C -0.2060(2) 0.07096(13) 0.82974(11) 0.0260(4) Uani 1 1 d . . . . .
H25 H -0.220749 0.004618 0.829241 0.031 Uiso 1 1 calc R U . . .
C26 C -0.0942(2) 0.08553(12) 0.86214(10) 0.0224(3) Uani 1 1 d . . . . .
H26 H -0.031999 0.029401 0.883691 0.027 Uiso 1 1 calc R U . . .
C27 C -0.00842(19) 0.19858(11) 1.01810(9) 0.0185(3) Uani 1 1 d . . . . .
C28 C -0.1540(2) 0.18672(12) 1.05386(10) 0.0253(3) Uani 1 1 d . . . . .
H28 H -0.214983 0.175296 1.021659 0.030 Uiso 1 1 calc R U . . .
C29 C -0.2086(3) 0.19185(15) 1.13732(12) 0.0384(5) Uani 1 1 d . . . . .
H29 H -0.308289 0.185607 1.162218 0.046 Uiso 1 1 calc R U . . .
C30 C -0.1176(3) 0.20606(15) 1.18407(11) 0.0416(6) Uani 1 1 d . . . . .
H30 H -0.154567 0.207557 1.241181 0.050 Uiso 1 1 calc R U . . .
C31 C 0.0266(3) 0.21809(13) 1.14845(11) 0.0347(5) Uani 1 1 d . . . . .
H31 H 0.088031 0.227708 1.181108 0.042 Uiso 1 1 calc R U . . .
C32 C 0.0813(2) 0.21610(12) 1.06527(10) 0.0249(3) Uani 1 1 d . . . . .
H32 H 0.179065 0.226567 1.040414 0.030 Uiso 1 1 calc R U . . .
C33 C 0.4687(3) 0.3275(2) 0.00739(17) 0.0552(7) Uani 1 1 d . . . . .
H33A H 0.506835 0.296032 -0.044910 0.066 Uiso 1 1 calc R U . . .
H33B H 0.554847 0.339724 0.023867 0.066 Uiso 1 1 calc R U . . .
C34 C 0.3662(4) 0.4259(2) -0.0042(2) 0.0658(9) Uani 1 1 d . . . . .
H34A H 0.279122 0.414091 -0.018899 0.099 Uiso 1 1 calc R U . . .
H34B H 0.418177 0.468633 -0.047679 0.099 Uiso 1 1 calc R U . . .
H34C H 0.333876 0.459742 0.046311 0.099 Uiso 1 1 calc R U . . .
H1D H 0.654(4) 0.295(3) 0.3730(19) 0.060(9) Uiso 1 1 d . . . . .
H2D H 0.501(4) 0.155(3) 0.3979(19) 0.081(12) Uiso 1 1 d D . . . .
H6D H 0.558(3) 0.338(2) 0.6523(16) 0.035(6) Uiso 1 1 d . . . . .
H7D H 0.591(3) 0.0605(19) 0.6031(15) 0.031(6) Uiso 1 1 d . . . . .
H9D H 0.146(4) 0.189(3) 0.3140(19) 0.059(9) Uiso 1 1 d . . . . .
H13D H 0.411(4) 0.437(3) 0.2204(19) 0.054(9) Uiso 1 1 d . . . . .
H14D H 0.332(3) 0.3346(18) 0.4619(14) 0.029(6) Uiso 1 1 d . . . . .
H15A H 0.178(4) 0.027(2) 0.3520(19) 0.054(8) Uiso 1 1 d . . . . .
H15B H 0.029(3) 0.063(2) 0.3526(16) 0.037(7) Uiso 1 1 d . . . . .
H16A H 0.380(4) 0.284(2) 0.110(2) 0.052(8) Uiso 1 1 d . . . . .
H1N H 1.294(3) 0.1410(16) 0.5527(13) 0.019(5) Uiso 1 1 d . . . . .
H2N H 1.231(3) 0.066(2) 0.5363(14) 0.027(6) Uiso 1 1 d . . . . .
H3N H 1.261(3) 0.1464(17) 0.4733(15) 0.025(5) Uiso 1 1 d . . . . .
H4N H -0.304(3) 0.4605(17) 0.5011(15) 0.022(5) Uiso 1 1 d . . . . .
H5N H -0.337(3) 0.438(2) 0.4266(15) 0.032(6) Uiso 1 1 d . . . . .
H6N H -0.376(3) 0.5379(19) 0.4526(14) 0.027(5) 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
P1 O3 1.4946(11) . ?
P1 O2 1.5329(12) . ?
P1 O1 1.5578(10) . ?
P1 C1 1.8444(15) . ?
P2 O5 1.4992(11) . ?
P2 O4 1.5069(10) . ?
P2 O6 1.5793(11) . ?
P2 C1 1.8505(15) . ?
P3 O10 1.5006(13) . ?
P3 O8 1.5170(12) . ?
P3 O9 1.5656(12) . ?
P3 C5 1.8575(15) . ?
P4 O11 1.4964(11) . ?
P4 O12 1.5073(11) . ?
P4 O13 1.5824(11) . ?
P4 C5 1.8499(15) . ?
P5 C27 1.7910(15) . ?
P5 C21 1.7927(16) . ?
P5 C9 1.7933(16) . ?
P5 C15 1.7956(15) . ?
O7 C1 1.4558(16) . ?
O14 C5 1.4323(17) . ?
O16 C33 1.404(3) . ?
N1 C4 1.4837(19) . ?
N2 C8 1.490(2) . ?
C1 C2 1.5334(19) . ?
C2 C3 1.523(2) . ?
C3 C4 1.518(2) . ?
C5 C6 1.546(2) . ?
C6 C7 1.533(2) . ?
C7 C8 1.510(2) . ?
C9 C10 1.399(2) . ?
C9 C14 1.402(2) . ?
C10 C11 1.390(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.389(3) . ?
C15 C16 1.392(2) . ?
C15 C20 1.396(2) . ?
C16 C17 1.392(2) . ?
C17 C18 1.378(3) . ?
C18 C19 1.388(3) . ?
C19 C20 1.388(2) . ?
C21 C22 1.394(2) . ?
C21 C26 1.402(2) . ?
C22 C23 1.387(3) . ?
C23 C24 1.386(3) . ?
C24 C25 1.393(3) . ?
C25 C26 1.387(2) . ?
C27 C28 1.395(2) . ?
C27 C32 1.398(2) . ?
C28 C29 1.392(3) . ?
C29 C30 1.385(4) . ?
C30 C31 1.384(4) . ?
C31 C32 1.384(3) . ?
C33 C34 1.490(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
O3 P1 O2 113.33(7) . . ?
O3 P1 O1 110.38(6) . . ?
O2 P1 O1 111.81(6) . . ?
O3 P1 C1 108.80(6) . . ?
O2 P1 C1 103.91(6) . . ?
O1 P1 C1 108.27(6) . . ?
O5 P2 O4 119.47(6) . . ?
O5 P2 O6 107.62(6) . . ?
O4 P2 O6 109.56(6) . . ?
O5 P2 C1 106.02(6) . . ?
O4 P2 C1 107.43(6) . . ?
O6 P2 C1 105.93(6) . . ?
O10 P3 O8 117.07(9) . . ?
O10 P3 O9 110.14(8) . . ?
O8 P3 O9 106.46(7) . . ?
O10 P3 C5 107.28(7) . . ?
O8 P3 C5 109.85(7) . . ?
O9 P3 C5 105.47(7) . . ?
O11 P4 O12 114.54(7) . . ?
O11 P4 O13 111.52(7) . . ?
O12 P4 O13 107.80(7) . . ?
O11 P4 C5 109.69(6) . . ?
O12 P4 C5 109.15(7) . . ?
O13 P4 C5 103.55(6) . . ?
C27 P5 C21 109.78(8) . . ?
C27 P5 C9 111.54(7) . . ?
C21 P5 C9 108.22(7) . . ?
C27 P5 C15 106.59(7) . . ?
C21 P5 C15 110.10(7) . . ?
C9 P5 C15 110.61(7) . . ?
O7 C1 C2 108.50(11) . . ?
O7 C1 P1 105.22(9) . . ?
C2 C1 P1 114.06(10) . . ?
O7 C1 P2 107.91(9) . . ?
C2 C1 P2 109.74(10) . . ?
P1 C1 P2 111.12(7) . . ?
C3 C2 C1 116.67(12) . . ?
C4 C3 C2 110.09(12) . . ?
N1 C4 C3 110.37(12) . . ?
O14 C5 C6 108.08(12) . . ?
O14 C5 P4 109.41(10) . . ?
C6 C5 P4 107.86(9) . . ?
O14 C5 P3 110.66(9) . . ?
C6 C5 P3 111.38(10) . . ?
P4 C5 P3 109.38(8) . . ?
C7 C6 C5 115.87(12) . . ?
C8 C7 C6 108.63(12) . . ?
N2 C8 C7 113.83(13) . . ?
C10 C9 C14 120.03(15) . . ?
C10 C9 P5 121.85(12) . . ?
C14 C9 P5 118.11(12) . . ?
C11 C10 C9 119.50(16) . . ?
C12 C11 C10 120.14(17) . . ?
C13 C12 C11 120.64(17) . . ?
C12 C13 C14 119.93(17) . . ?
C13 C14 C9 119.75(17) . . ?
C16 C15 C20 120.27(14) . . ?
C16 C15 P5 121.07(12) . . ?
C20 C15 P5 118.62(12) . . ?
C15 C16 C17 119.12(16) . . ?
C18 C17 C16 120.73(17) . . ?
C17 C18 C19 120.16(16) . . ?
C20 C19 C18 119.98(17) . . ?
C19 C20 C15 119.72(16) . . ?
C22 C21 C26 120.11(15) . . ?
C22 C21 P5 121.26(12) . . ?
C26 C21 P5 118.57(12) . . ?
C23 C22 C21 119.82(15) . . ?
C24 C23 C22 120.25(16) . . ?
C23 C24 C25 120.14(17) . . ?
C26 C25 C24 120.18(16) . . ?
C25 C26 C21 119.49(15) . . ?
C28 C27 C32 120.53(15) . . ?
C28 C27 P5 121.36(13) . . ?
C32 C27 P5 117.95(13) . . ?
C29 C28 C27 119.17(18) . . ?
C30 C29 C28 120.0(2) . . ?
C31 C30 C29 120.71(17) . . ?
C32 C31 C30 120.03(19) . . ?
C31 C32 C27 119.49(19) . . ?
O16 C33 C34 112.6(2) . . ?

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
O3 P1 C1 O7 -48.36(10) . . . . ?
O2 P1 C1 O7 72.66(10) . . . . ?
O1 P1 C1 O7 -168.34(9) . . . . ?
O3 P1 C1 C2 70.42(11) . . . . ?
O2 P1 C1 C2 -168.56(10) . . . . ?
O1 P1 C1 C2 -49.56(11) . . . . ?
O3 P1 C1 P2 -164.90(7) . . . . ?
O2 P1 C1 P2 -43.87(8) . . . . ?
O1 P1 C1 P2 75.12(8) . . . . ?
O5 P2 C1 O7 -26.34(11) . . . . ?
O4 P2 C1 O7 -155.13(9) . . . . ?
O6 P2 C1 O7 87.83(10) . . . . ?
O5 P2 C1 C2 -144.39(9) . . . . ?
O4 P2 C1 C2 86.82(10) . . . . ?
O6 P2 C1 C2 -30.22(10) . . . . ?
O5 P2 C1 P1 88.53(8) . . . . ?
O4 P2 C1 P1 -40.26(9) . . . . ?
O6 P2 C1 P1 -157.30(7) . . . . ?
O7 C1 C2 C3 67.00(15) . . . . ?
P1 C1 C2 C3 -49.90(15) . . . . ?
P2 C1 C2 C3 -175.31(10) . . . . ?
C1 C2 C3 C4 -163.04(12) . . . . ?
C2 C3 C4 N1 179.77(11) . . . . ?
O11 P4 C5 O14 61.16(11) . . . . ?
O12 P4 C5 O14 -65.08(11) . . . . ?
O13 P4 C5 O14 -179.70(9) . . . . ?
O11 P4 C5 C6 178.50(10) . . . . ?
O12 P4 C5 C6 52.26(11) . . . . ?
O13 P4 C5 C6 -62.35(11) . . . . ?
O11 P4 C5 P3 -60.20(9) . . . . ?
O12 P4 C5 P3 173.55(7) . . . . ?
O13 P4 C5 P3 58.94(8) . . . . ?
O10 P3 C5 O14 -155.02(10) . . . . ?
O8 P3 C5 O14 -26.78(12) . . . . ?
O9 P3 C5 O14 87.57(11) . . . . ?
O10 P3 C5 C6 84.72(11) . . . . ?
O8 P3 C5 C6 -147.04(10) . . . . ?
O9 P3 C5 C6 -32.69(11) . . . . ?
O10 P3 C5 P4 -34.42(10) . . . . ?
O8 P3 C5 P4 93.82(9) . . . . ?
O9 P3 C5 P4 -151.82(7) . . . . ?
O14 C5 C6 C7 -39.68(17) . . . . ?
P4 C5 C6 C7 -157.87(11) . . . . ?
P3 C5 C6 C7 82.09(14) . . . . ?
C5 C6 C7 C8 174.98(13) . . . . ?
C6 C7 C8 N2 -177.82(13) . . . . ?
C27 P5 C9 C10 -11.68(16) . . . . ?
C21 P5 C9 C10 -132.54(13) . . . . ?
C15 P5 C9 C10 106.77(14) . . . . ?
C27 P5 C9 C14 168.56(13) . . . . ?
C21 P5 C9 C14 47.69(15) . . . . ?
C15 P5 C9 C14 -72.99(14) . . . . ?
C14 C9 C10 C11 0.4(2) . . . . ?
P5 C9 C10 C11 -179.35(13) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C9 0.1(3) . . . . ?
C10 C9 C14 C13 -0.3(3) . . . . ?
P5 C9 C14 C13 179.46(14) . . . . ?
C27 P5 C15 C16 138.68(14) . . . . ?
C21 P5 C15 C16 -102.30(15) . . . . ?
C9 P5 C15 C16 17.26(16) . . . . ?
C27 P5 C15 C20 -43.35(15) . . . . ?
C21 P5 C15 C20 75.67(15) . . . . ?
C9 P5 C15 C20 -164.77(13) . . . . ?
C20 C15 C16 C17 0.9(3) . . . . ?
P5 C15 C16 C17 178.81(14) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C15 -1.2(3) . . . . ?
C16 C15 C20 C19 0.2(3) . . . . ?
P5 C15 C20 C19 -177.76(15) . . . . ?
C27 P5 C21 C22 96.85(15) . . . . ?
C9 P5 C21 C22 -141.21(14) . . . . ?
C15 P5 C21 C22 -20.21(16) . . . . ?
C27 P5 C21 C26 -80.22(14) . . . . ?
C9 P5 C21 C26 41.72(15) . . . . ?
C15 P5 C21 C26 162.72(13) . . . . ?
C26 C21 C22 C23 0.9(3) . . . . ?
P5 C21 C22 C23 -176.10(14) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C21 0.2(3) . . . . ?
C22 C21 C26 C25 -0.7(3) . . . . ?
P5 C21 C26 C25 176.41(13) . . . . ?
C21 P5 C27 C28 -1.31(15) . . . . ?
C9 P5 C27 C28 -121.26(14) . . . . ?
C15 P5 C27 C28 117.92(14) . . . . ?
C21 P5 C27 C32 -176.82(12) . . . . ?
C9 P5 C27 C32 63.23(14) . . . . ?
C15 P5 C27 C32 -57.59(14) . . . . ?
C32 C27 C28 C29 -0.4(2) . . . . ?
P5 C27 C28 C29 -175.84(14) . . . . ?
C27 C28 C29 C30 -1.6(3) . . . . ?
C28 C29 C30 C31 1.8(3) . . . . ?
C29 C30 C31 C32 0.1(3) . . . . ?
C30 C31 C32 C27 -2.1(3) . . . . ?
C28 C27 C32 C31 2.3(2) . . . . ?
P5 C27 C32 C31 177.83(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1D O11 0.94(3) 1.58(3) 2.4915(15) 162(3) . yes
O2 H2D O8 0.875(18) 1.53(2) 2.3927(16) 167(4) . yes
O6 H6D O12 0.80(3) 1.81(3) 2.6088(15) 178(3) 2_666 yes
O7 H7D O5 0.88(3) 2.13(3) 2.7877(16) 131(2) . yes
O9 H9D O15 0.84(3) 1.73(3) 2.5682(16) 173(3) . yes
O13 H13D O10 0.82(3) 1.85(3) 2.6253(18) 157(3) . yes
O14 H14D O4 0.87(3) 1.91(3) 2.7312(15) 157(2) . yes
O15 H15A O7 0.84(3) 2.01(3) 2.8489(16) 177(3) 2_656 yes
O15 H15B O3 0.84(3) 1.88(3) 2.7234(17) 176(3) 1_455 yes
O16 H16A O10 0.81(3) 1.96(3) 2.749(2) 162(3) . yes
N1 H1N O5 0.88(2) 1.83(2) 2.6969(17) 169(2) 1_655 yes
N1 H2N O3 0.84(3) 2.01(3) 2.8065(17) 158(2) 2_756 yes
N1 H3N O8 0.93(2) 2.26(2) 3.176(2) 167(2) 1_655 yes
N2 H4N O12 0.89(2) 2.01(2) 2.8691(19) 161(2) 2_566 yes
N2 H5N O11 0.87(3) 2.23(3) 3.0389(19) 155(2) 1_455 yes
N2 H6N O4 0.89(3) 1.85(3) 2.7021(17) 160(2) 2_566 yes

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_compound3a_Ph3PEtLH4
_database_code_depnum_ccdc_archive 'CCDC 2505727'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 P, C4 H12 N O7 P2'
_chemical_formula_sum            'C24 H32 N O7 P3'
_chemical_formula_weight         539.41

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'
N N 0.0311 0.0180 '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                   9.58800(10)
_cell_length_b                   9.68110(10)
_cell_length_c                   13.9927(2)
_cell_angle_alpha                91.4490(10)
_cell_angle_beta                 99.3600(10)
_cell_angle_gamma                98.0690(10)
_cell_volume                     1267.32(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    12757
_cell_measurement_theta_min      4.6080
_cell_measurement_theta_max      79.5500

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    2.544
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.95172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            18943
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.619
_diffrn_reflns_theta_max         79.755
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5374
_reflns_number_gt                5071
_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 system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0409P)²+0.4995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         5374
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
P1 P 0.11873(3) 0.50481(3) 0.83571(2) 0.01173(8) Uani 1 1 d . . . . .
P2 P 0.16598(3) 0.80872(3) 0.89371(2) 0.01214(8) Uani 1 1 d . . . . .
P3 P 0.67954(3) 0.06360(3) 0.69749(2) 0.01289(8) Uani 1 1 d . . . . .
O1 O 0.10098(10) 0.55845(9) 0.73478(7) 0.01678(19) Uani 1 1 d . . . . .
O2 O -0.02892(10) 0.50028(10) 0.87717(7) 0.01713(19) Uani 1 1 d . . . . .
O3 O 0.16579(10) 0.36520(9) 0.84872(7) 0.01823(19) Uani 1 1 d . . . . .
O4 O 0.16988(11) 0.82654(10) 0.78092(7) 0.0188(2) Uani 1 1 d . . . . .
O5 O 0.01223(10) 0.77537(9) 0.90960(7) 0.01762(19) Uani 1 1 d . . . . .
O6 O 0.25575(10) 0.93306(9) 0.94887(7) 0.01809(19) Uani 1 1 d . . . . .
O7 O 0.24229(10) 0.61022(9) 1.01672(6) 0.01444(18) Uani 1 1 d . . . . .
N1 N 0.77670(11) 0.79752(11) 0.99986(8) 0.0135(2) Uani 1 1 d . . . . .
C1 C 0.23905(13) 0.64272(12) 0.91658(9) 0.0114(2) Uani 1 1 d . . . . .
C2 C 0.39077(13) 0.64425(13) 0.89482(9) 0.0142(2) Uani 1 1 d . . . . .
H2A H 0.393583 0.679186 0.829170 0.017 Uiso 1 1 calc R U . . .
H2B H 0.411196 0.546843 0.893369 0.017 Uiso 1 1 calc R U . . .
C3 C 0.51040(13) 0.73252(13) 0.96620(9) 0.0151(2) Uani 1 1 d . . . . .
H3A H 0.492205 0.830547 0.969590 0.018 Uiso 1 1 calc R U . . .
H3B H 0.514269 0.695837 1.031837 0.018 Uiso 1 1 calc R U . . .
C4 C 0.65119(13) 0.72555(13) 0.93062(9) 0.0147(2) Uani 1 1 d . . . . .
H4A H 0.662715 0.626443 0.920716 0.018 Uiso 1 1 calc R U . . .
H4B H 0.648389 0.769187 0.867241 0.018 Uiso 1 1 calc R U . . .
C5 C 0.65660(14) -0.12361(13) 0.68063(9) 0.0148(2) Uani 1 1 d . . . . .
C6 C 0.77783(14) -0.19145(14) 0.69050(10) 0.0175(3) Uani 1 1 d . . . . .
H6 H 0.870691 -0.138489 0.701425 0.021 Uiso 1 1 calc R U . . .
C7 C 0.76147(16) -0.33621(14) 0.68423(10) 0.0211(3) Uani 1 1 d . . . . .
H7 H 0.843209 -0.382703 0.691569 0.025 Uiso 1 1 calc R U . . .
C8 C 0.62533(17) -0.41319(14) 0.66719(11) 0.0232(3) Uani 1 1 d . . . . .
H8 H 0.614638 -0.512330 0.663508 0.028 Uiso 1 1 calc R U . . .
C9 C 0.50471(15) -0.34670(14) 0.65549(10) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.412147 -0.400198 0.642763 0.026 Uiso 1 1 calc R U . . .
C10 C 0.51990(14) -0.20143(14) 0.66248(10) 0.0174(3) Uani 1 1 d . . . . .
H10 H 0.437811 -0.155455 0.654946 0.021 Uiso 1 1 calc R U . . .
C11 C 0.51067(14) 0.12650(13) 0.67676(10) 0.0160(2) Uani 1 1 d . . . . .
C12 C 0.41689(15) 0.09668(14) 0.74338(10) 0.0202(3) Uani 1 1 d . . . . .
H12 H 0.438003 0.035425 0.793994 0.024 Uiso 1 1 calc R U . . .
C13 C 0.29367(16) 0.15741(16) 0.73447(12) 0.0256(3) Uani 1 1 d . . . . .
H13 H 0.228890 0.136529 0.778535 0.031 Uiso 1 1 calc R U . . .
C14 C 0.26387(16) 0.24886(16) 0.66144(12) 0.0272(3) Uani 1 1 d . . . . .
H14 H 0.181034 0.293350 0.657572 0.033 Uiso 1 1 calc R U . . .
C15 C 0.35445(16) 0.27542(15) 0.59429(11) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.331625 0.335276 0.543093 0.029 Uiso 1 1 calc R U . . .
C16 C 0.47886(15) 0.21468(14) 0.60155(10) 0.0187(3) Uani 1 1 d . . . . .
H16 H 0.541370 0.233134 0.555753 0.022 Uiso 1 1 calc R U . . .
C17 C 0.78653(13) 0.13998(13) 0.61328(9) 0.0146(2) Uani 1 1 d . . . . .
C18 C 0.78966(15) 0.06740(14) 0.52640(10) 0.0192(3) Uani 1 1 d . . . . .
H18 H 0.744005 -0.026547 0.514995 0.023 Uiso 1 1 calc R U . . .
C19 C 0.85971(16) 0.13283(15) 0.45657(10) 0.0231(3) Uani 1 1 d . . . . .
H19 H 0.862345 0.083723 0.397397 0.028 Uiso 1 1 calc R U . . .
C20 C 0.92608(16) 0.27085(15) 0.47378(10) 0.0238(3) Uani 1 1 d . . . . .
H20 H 0.972032 0.316478 0.425521 0.029 Uiso 1 1 calc R U . . .
C21 C 0.92538(16) 0.34186(14) 0.56093(11) 0.0224(3) Uani 1 1 d . . . . .
H21 H 0.972800 0.435163 0.572632 0.027 Uiso 1 1 calc R U . . .
C22 C 0.85581(15) 0.27751(14) 0.63128(10) 0.0184(3) Uani 1 1 d . . . . .
H22 H 0.855283 0.326337 0.690937 0.022 Uiso 1 1 calc R U . . .
C23 C 0.75968(14) 0.12003(14) 0.82014(9) 0.0176(3) Uani 1 1 d . . . . .
H23A H 0.760895 0.222154 0.827817 0.021 Uiso 1 1 calc R U . . .
H23B H 0.698491 0.074962 0.864503 0.021 Uiso 1 1 calc R U . . .
C24 C 0.91102(15) 0.08823(15) 0.85134(10) 0.0206(3) Uani 1 1 d . . . . .
H24A H 0.911210 -0.012842 0.845639 0.031 Uiso 1 1 calc R U . . .
H24B H 0.945513 0.121877 0.918852 0.031 Uiso 1 1 calc R U . . .
H24C H 0.973781 0.135184 0.809622 0.031 Uiso 1 1 calc R U . . .
H2 H -0.038(2) 0.582(3) 0.8866(17) 0.043(6) Uiso 1 1 d . . . . .
H4 H 0.141(3) 0.745(3) 0.7531(18) 0.050(7) Uiso 1 1 d . . . . .
H7A H 0.163(2) 0.592(2) 1.0319(15) 0.032(5) Uiso 1 1 d . . . . .
H1N H 0.857(2) 0.8031(19) 0.9713(13) 0.023(4) Uiso 1 1 d . . . . .
H2N H 0.767(2) 0.884(2) 1.0178(13) 0.023(4) Uiso 1 1 d . . . . .
H3N H 0.792(2) 0.744(2) 1.0533(14) 0.024(4) 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
P1 O3 1.4902(9) . ?
P1 O1 1.5089(9) . ?
P1 O2 1.6104(9) . ?
P1 C1 1.8602(12) . ?
P2 O6 1.4939(9) . ?
P2 O5 1.5177(9) . ?
P2 O4 1.5978(10) . ?
P2 C1 1.8561(12) . ?
P3 C11 1.7915(13) . ?
P3 C17 1.7921(13) . ?
P3 C5 1.7996(13) . ?
P3 C23 1.8000(13) . ?
O7 C1 1.4403(14) . ?
N1 C4 1.4912(16) . ?
C1 C2 1.5321(16) . ?
C2 C3 1.5338(17) . ?
C3 C4 1.5222(16) . ?
C5 C10 1.3981(18) . ?
C5 C6 1.4030(18) . ?
C6 C7 1.3871(19) . ?
C7 C8 1.390(2) . ?
C8 C9 1.390(2) . ?
C9 C10 1.3927(19) . ?
C11 C16 1.3940(19) . ?
C11 C12 1.4050(19) . ?
C12 C13 1.381(2) . ?
C13 C14 1.390(2) . ?
C14 C15 1.385(2) . ?
C15 C16 1.393(2) . ?
C17 C18 1.3953(19) . ?
C17 C22 1.3992(18) . ?
C18 C19 1.3901(19) . ?
C19 C20 1.394(2) . ?
C20 C21 1.386(2) . ?
C21 C22 1.3892(19) . ?
C23 C24 1.5223(19) . ?

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
O3 P1 O1 117.63(6) . . ?
O3 P1 O2 107.47(5) . . ?
O1 P1 O2 109.65(5) . . ?
O3 P1 C1 111.77(6) . . ?
O1 P1 C1 107.08(5) . . ?
O2 P1 C1 102.13(5) . . ?
O6 P2 O5 117.42(5) . . ?
O6 P2 O4 108.18(5) . . ?
O5 P2 O4 109.71(5) . . ?
O6 P2 C1 113.82(5) . . ?
O5 P2 C1 103.98(5) . . ?
O4 P2 C1 102.71(5) . . ?
C11 P3 C17 108.65(6) . . ?
C11 P3 C5 110.98(6) . . ?
C17 P3 C5 109.12(6) . . ?
C11 P3 C23 105.93(6) . . ?
C17 P3 C23 110.76(6) . . ?
C5 P3 C23 111.34(6) . . ?
O7 C1 C2 107.27(10) . . ?
O7 C1 P2 109.95(8) . . ?
C2 C1 P2 114.32(8) . . ?
O7 C1 P1 110.53(8) . . ?
C2 C1 P1 107.94(8) . . ?
P2 C1 P1 106.84(6) . . ?
C1 C2 C3 115.91(10) . . ?
C4 C3 C2 108.17(10) . . ?
N1 C4 C3 112.53(10) . . ?
C10 C5 C6 120.17(12) . . ?
C10 C5 P3 120.62(10) . . ?
C6 C5 P3 119.14(10) . . ?
C7 C6 C5 119.68(12) . . ?
C6 C7 C8 119.93(13) . . ?
C9 C8 C7 120.72(13) . . ?
C8 C9 C10 119.82(13) . . ?
C9 C10 C5 119.66(13) . . ?
C16 C11 C12 120.47(12) . . ?
C16 C11 P3 120.56(10) . . ?
C12 C11 P3 118.67(10) . . ?
C13 C12 C11 119.27(13) . . ?
C12 C13 C14 120.41(14) . . ?
C15 C14 C13 120.27(14) . . ?
C14 C15 C16 120.23(14) . . ?
C15 C16 C11 119.28(13) . . ?
C18 C17 C22 120.34(12) . . ?
C18 C17 P3 120.05(10) . . ?
C22 C17 P3 119.34(10) . . ?
C19 C18 C17 119.88(12) . . ?
C18 C19 C20 119.69(13) . . ?
C21 C20 C19 120.35(13) . . ?
C20 C21 C22 120.45(13) . . ?
C21 C22 C17 119.26(12) . . ?
C24 C23 P3 115.18(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 P2 C1 O7 63.61(9) . . . . ?
O5 P2 C1 O7 -65.34(9) . . . . ?
O4 P2 C1 O7 -179.70(8) . . . . ?
O6 P2 C1 C2 -57.08(10) . . . . ?
O5 P2 C1 C2 173.96(9) . . . . ?
O4 P2 C1 C2 59.60(10) . . . . ?
O6 P2 C1 P1 -176.41(5) . . . . ?
O5 P2 C1 P1 54.63(7) . . . . ?
O4 P2 C1 P1 -59.72(7) . . . . ?
O3 P1 C1 O7 -59.58(9) . . . . ?
O1 P1 C1 O7 170.24(8) . . . . ?
O2 P1 C1 O7 55.03(9) . . . . ?
O3 P1 C1 C2 57.44(9) . . . . ?
O1 P1 C1 C2 -72.74(9) . . . . ?
O2 P1 C1 C2 172.05(8) . . . . ?
O3 P1 C1 P2 -179.18(5) . . . . ?
O1 P1 C1 P2 50.64(7) . . . . ?
O2 P1 C1 P2 -64.57(7) . . . . ?
O7 C1 C2 C3 -50.34(13) . . . . ?
P2 C1 C2 C3 71.83(12) . . . . ?
P1 C1 C2 C3 -169.46(9) . . . . ?
C1 C2 C3 C4 -177.85(10) . . . . ?
C2 C3 C4 N1 -174.75(10) . . . . ?
C11 P3 C5 C10 -5.21(13) . . . . ?
C17 P3 C5 C10 -124.92(11) . . . . ?
C23 P3 C5 C10 112.52(11) . . . . ?
C11 P3 C5 C6 177.79(10) . . . . ?
C17 P3 C5 C6 58.09(12) . . . . ?
C23 P3 C5 C6 -64.47(12) . . . . ?
C10 C5 C6 C7 -1.38(19) . . . . ?
P3 C5 C6 C7 175.63(10) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 C5 0.4(2) . . . . ?
C6 C5 C10 C9 0.8(2) . . . . ?
P3 C5 C10 C9 -176.13(10) . . . . ?
C17 P3 C11 C16 2.88(13) . . . . ?
C5 P3 C11 C16 -117.10(11) . . . . ?
C23 P3 C11 C16 121.92(11) . . . . ?
C17 P3 C11 C12 -170.88(10) . . . . ?
C5 P3 C11 C12 69.14(12) . . . . ?
C23 P3 C11 C12 -51.84(12) . . . . ?
C16 C11 C12 C13 -1.0(2) . . . . ?
P3 C11 C12 C13 172.79(11) . . . . ?
C11 C12 C13 C14 -1.1(2) . . . . ?
C12 C13 C14 C15 2.8(2) . . . . ?
C13 C14 C15 C16 -2.4(2) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C12 C11 C16 C15 1.4(2) . . . . ?
P3 C11 C16 C15 -172.29(10) . . . . ?
C11 P3 C17 C18 -95.34(12) . . . . ?
C5 P3 C17 C18 25.79(13) . . . . ?
C23 P3 C17 C18 148.70(11) . . . . ?
C11 P3 C17 C22 78.74(12) . . . . ?
C5 P3 C17 C22 -160.13(10) . . . . ?
C23 P3 C17 C22 -37.22(13) . . . . ?
C22 C17 C18 C19 -1.2(2) . . . . ?
P3 C17 C18 C19 172.83(11) . . . . ?
C17 C18 C19 C20 -0.2(2) . . . . ?
C18 C19 C20 C21 1.5(2) . . . . ?
C19 C20 C21 C22 -1.5(2) . . . . ?
C20 C21 C22 C17 0.1(2) . . . . ?
C18 C17 C22 C21 1.2(2) . . . . ?
P3 C17 C22 C21 -172.83(11) . . . . ?
C11 P3 C23 C24 -175.16(10) . . . . ?
C17 P3 C23 C24 -57.53(11) . . . . ?
C5 P3 C23 C24 64.09(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O5 0.82(2) 1.87(2) 2.6533(13) 159(2) . yes
O4 H4 O1 0.86(3) 1.80(3) 2.6239(13) 161(2) . yes
O7 H7A O2 0.82(2) 2.08(2) 2.8263(13) 151(2) 2_567 yes
N1 H1N O5 0.92(2) 1.88(2) 2.7912(14) 168.5(17) 1_655 yes
N1 H2N O6 0.89(2) 1.87(2) 2.7605(14) 178.0(18) 2_677 yes
N1 H3N O3 0.92(2) 1.78(2) 2.7032(15) 174.7(18) 2_667 yes

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_compound5_Ph3BnLH4
_database_code_depnum_ccdc_archive 'CCDC 2505721'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 P, C4 H12 N O7 P2, C2 H3 N, H2 O'
_chemical_formula_sum            'C31 H39 N2 O8 P3'
_chemical_formula_weight         660.55

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'
N N 0.0311 0.0180 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   19.0320(3)
_cell_length_b                   9.1890(2)
_cell_length_c                   18.6815(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.833(2)
_cell_angle_gamma                90
_cell_volume                     3208.89(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    12013
_cell_measurement_theta_min      4.7140
_cell_measurement_theta_max      79.6350

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    2.148
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.51038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            28642
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.731
_diffrn_reflns_theta_max         80.821
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6898
_reflns_number_gt                5774
_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 1.171.43.95a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_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)+(0.0666P)²+2.1013P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         6898
_refine_ls_number_parameters     430
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
P1 P 0.94367(3) 0.88130(5) 0.64643(3) 0.01629(12) Uani 1 1 d . . . . .
P2 P 0.88291(3) 0.58075(5) 0.66642(3) 0.01560(12) Uani 1 1 d . . . . .
P3 P 0.68005(3) 0.31989(6) 0.50024(3) 0.01979(13) Uani 1 1 d . . . . .
O1 O 0.86056(8) 0.91911(16) 0.63386(9) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.97723(8) 0.97942(15) 0.59841(8) 0.0209(3) Uani 1 1 d . . . . .
O3 O 0.97650(8) 0.88930(16) 0.72663(8) 0.0221(3) Uani 1 1 d . . . . .
O4 O 0.81508(7) 0.66860(16) 0.66096(8) 0.0218(3) Uani 1 1 d . . . . .
O5 O 0.87379(8) 0.43069(15) 0.63300(8) 0.0194(3) Uani 1 1 d . . . . .
O6 O 0.92048(8) 0.57158(15) 0.74855(7) 0.0190(3) Uani 1 1 d . . . . .
O7 O 1.01611(7) 0.62938(15) 0.64195(8) 0.0187(3) Uani 1 1 d . . . . .
O8 O 0.87506(10) 0.18829(19) 0.72602(9) 0.0297(4) Uani 1 1 d . . . . .
N1 N 0.99979(9) 0.73326(19) 0.36722(9) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.68754(17) -0.0403(3) 0.69574(19) 0.0698(10) Uani 1 1 d . . . . .
C1 C 0.94537(10) 0.6869(2) 0.62071(10) 0.0155(4) Uani 1 1 d . . . . .
C2 C 0.92265(10) 0.6664(2) 0.53806(10) 0.0168(4) Uani 1 1 d . . . . .
H2A H 0.911106 0.562411 0.528166 0.020 Uiso 1 1 calc R U . . .
H2B H 0.878325 0.722867 0.521258 0.020 Uiso 1 1 calc R U . . .
C3 C 0.97819(10) 0.7124(2) 0.49313(10) 0.0178(4) Uani 1 1 d . . . . .
H3A H 0.991557 0.815536 0.503277 0.021 Uiso 1 1 calc R U . . .
H3B H 1.021800 0.652196 0.506582 0.021 Uiso 1 1 calc R U . . .
C4 C 0.94709(10) 0.6933(2) 0.41284(10) 0.0176(4) Uani 1 1 d . . . . .
H4A H 0.932415 0.590654 0.403353 0.021 Uiso 1 1 calc R U . . .
H4B H 0.904005 0.755108 0.399562 0.021 Uiso 1 1 calc R U . . .
C5 C 0.67425(11) 0.5037(2) 0.46590(12) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.72348(11) 0.6083(2) 0.49786(13) 0.0259(4) Uani 1 1 d . . . . .
H6 H 0.756490 0.586326 0.541292 0.031 Uiso 1 1 calc R U . . .
C7 C 0.72403(13) 0.7447(3) 0.46596(15) 0.0317(5) Uani 1 1 d . . . . .
H7 H 0.756142 0.817416 0.488660 0.038 Uiso 1 1 calc R U . . .
C8 C 0.67741(13) 0.7751(3) 0.40052(15) 0.0335(5) Uani 1 1 d . . . . .
H8 H 0.679455 0.866622 0.377392 0.040 Uiso 1 1 calc R U . . .
C9 C 0.62814(13) 0.6712(3) 0.36943(14) 0.0326(5) Uani 1 1 d . . . . .
H9 H 0.595702 0.692958 0.325560 0.039 Uiso 1 1 calc R U . . .
C10 C 0.62578(12) 0.5367(3) 0.40157(12) 0.0274(5) Uani 1 1 d . . . . .
H10 H 0.591457 0.466620 0.380248 0.033 Uiso 1 1 calc R U . . .
C11 C 0.74200(11) 0.2247(2) 0.45591(12) 0.0220(4) Uani 1 1 d . . . . .
C12 C 0.73299(13) 0.2325(3) 0.37982(13) 0.0309(5) Uani 1 1 d . . . . .
H12 H 0.693541 0.284066 0.352687 0.037 Uiso 1 1 calc R U . . .
C13 C 0.78171(13) 0.1648(3) 0.34418(14) 0.0358(6) Uani 1 1 d . . . . .
H13 H 0.775129 0.168450 0.292530 0.043 Uiso 1 1 calc R U . . .
C14 C 0.84026(13) 0.0914(3) 0.38401(14) 0.0313(5) Uani 1 1 d . . . . .
H14 H 0.874194 0.047262 0.359495 0.038 Uiso 1 1 calc R U . . .
C15 C 0.84927(12) 0.0825(2) 0.45908(14) 0.0282(5) Uani 1 1 d . . . . .
H15 H 0.889052 0.031234 0.485832 0.034 Uiso 1 1 calc R U . . .
C16 C 0.80011(11) 0.1485(2) 0.49580(12) 0.0246(4) Uani 1 1 d . . . . .
H16 H 0.806107 0.141765 0.547331 0.029 Uiso 1 1 calc R U . . .
C17 C 0.59243(11) 0.2414(2) 0.47491(11) 0.0220(4) Uani 1 1 d . . . . .
C18 C 0.58149(12) 0.1164(3) 0.43249(13) 0.0288(5) Uani 1 1 d . . . . .
H18 H 0.620938 0.068948 0.418057 0.035 Uiso 1 1 calc R U . . .
C19 C 0.51269(14) 0.0605(3) 0.41108(14) 0.0343(5) Uani 1 1 d . . . . .
H19 H 0.505354 -0.026003 0.382772 0.041 Uiso 1 1 calc R U . . .
C20 C 0.45514(13) 0.1308(3) 0.43102(13) 0.0331(5) Uani 1 1 d . . . . .
H20 H 0.408145 0.093921 0.415255 0.040 Uiso 1 1 calc R U . . .
C21 C 0.46568(12) 0.2551(3) 0.47401(13) 0.0296(5) Uani 1 1 d . . . . .
H21 H 0.426048 0.302030 0.488342 0.036 Uiso 1 1 calc R U . . .
C22 C 0.53418(11) 0.3108(2) 0.49604(12) 0.0244(4) Uani 1 1 d . . . . .
H22 H 0.541447 0.395850 0.525408 0.029 Uiso 1 1 calc R U . . .
C23 C 0.71076(11) 0.3146(2) 0.59822(11) 0.0241(4) Uani 1 1 d . . . . .
H23A H 0.720531 0.212020 0.613079 0.029 Uiso 1 1 calc R U . . .
H23B H 0.756559 0.368284 0.610139 0.029 Uiso 1 1 calc R U . . .
C24 C 0.65948(11) 0.3777(2) 0.64290(11) 0.0230(4) Uani 1 1 d . . . . .
C25 C 0.61368(12) 0.2860(3) 0.67189(13) 0.0283(5) Uani 1 1 d . . . . .
H25 H 0.614002 0.184403 0.662611 0.034 Uiso 1 1 calc R U . . .
C26 C 0.56758(13) 0.3423(3) 0.71425(14) 0.0344(5) Uani 1 1 d . . . . .
H26 H 0.537108 0.278865 0.734529 0.041 Uiso 1 1 calc R U . . .
C27 C 0.56577(14) 0.4904(3) 0.72712(14) 0.0364(6) Uani 1 1 d . . . . .
H27 H 0.533241 0.528867 0.755072 0.044 Uiso 1 1 calc R U . . .
C28 C 0.61148(15) 0.5822(3) 0.69917(14) 0.0369(6) Uani 1 1 d . . . . .
H28 H 0.610538 0.683884 0.708202 0.044 Uiso 1 1 calc R U . . .
C29 C 0.65881(13) 0.5262(3) 0.65789(13) 0.0307(5) Uani 1 1 d . . . . .
H29 H 0.690881 0.589466 0.639789 0.037 Uiso 1 1 calc R U . . .
C30 C 0.73646(15) -0.0638(3) 0.73907(16) 0.0414(6) Uani 1 1 d . . . . .
C31 C 0.79885(14) -0.0946(3) 0.79433(14) 0.0383(6) Uani 1 1 d . . . . .
H31A H 0.818119 -0.190248 0.785047 0.057 Uiso 1 1 calc R U . . .
H31B H 0.785370 -0.094670 0.842450 0.057 Uiso 1 1 calc R U . . .
H31C H 0.835283 -0.019882 0.792924 0.057 Uiso 1 1 calc R U . . .
H1A H 0.836(2) 0.834(5) 0.645(2) 0.073(13) Uiso 1 1 d . . . . .
H6A H 0.960(2) 0.500(5) 0.759(2) 0.079(13) Uiso 1 1 d . . . . .
H7A H 1.0358(18) 0.652(4) 0.684(2) 0.045(9) Uiso 1 1 d . . . . .
H8A H 0.8716(17) 0.259(4) 0.6999(18) 0.037(8) Uiso 1 1 d . . . . .
H8B H 0.865(2) 0.109(5) 0.696(2) 0.072(13) Uiso 1 1 d . . . . .
H1N H 1.0402(16) 0.681(3) 0.3737(15) 0.026(7) Uiso 1 1 d . . . . .
H2N H 1.0123(15) 0.829(3) 0.3733(16) 0.030(7) Uiso 1 1 d . . . . .
H3N H 0.9832(16) 0.717(3) 0.3195(18) 0.034(8) 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
P1 O2 1.4970(15) . ?
P1 O3 1.5129(14) . ?
P1 O1 1.5932(15) . ?
P1 C1 1.8519(19) . ?
P2 O4 1.5097(15) . ?
P2 O5 1.5102(14) . ?
P2 O6 1.5685(14) . ?
P2 C1 1.864(2) . ?
P3 C11 1.791(2) . ?
P3 C17 1.797(2) . ?
P3 C5 1.802(2) . ?
P3 C23 1.814(2) . ?
O7 C1 1.431(2) . ?
N1 C4 1.479(3) . ?
N2 C30 1.134(4) . ?
C1 C2 1.535(2) . ?
C2 C3 1.528(3) . ?
C3 C4 1.516(2) . ?
C5 C6 1.396(3) . ?
C5 C10 1.404(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.397(4) . ?
C8 C9 1.387(4) . ?
C9 C10 1.378(3) . ?
C11 C16 1.399(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.383(4) . ?
C15 C16 1.398(3) . ?
C17 C18 1.389(3) . ?
C17 C22 1.399(3) . ?
C18 C19 1.393(3) . ?
C19 C20 1.382(4) . ?
C20 C21 1.389(4) . ?
C21 C22 1.389(3) . ?
C23 C24 1.514(3) . ?
C24 C25 1.393(3) . ?
C24 C29 1.394(3) . ?
C25 C26 1.387(4) . ?
C26 C27 1.383(4) . ?
C27 C28 1.383(4) . ?
C28 C29 1.390(4) . ?
C30 C31 1.447(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
O2 P1 O3 114.89(8) . . ?
O2 P1 O1 107.69(8) . . ?
O3 P1 O1 110.44(9) . . ?
O2 P1 C1 113.28(9) . . ?
O3 P1 C1 106.24(8) . . ?
O1 P1 C1 103.74(8) . . ?
O4 P2 O5 115.46(8) . . ?
O4 P2 O6 108.76(8) . . ?
O5 P2 O6 110.56(8) . . ?
O4 P2 C1 107.47(8) . . ?
O5 P2 C1 108.77(9) . . ?
O6 P2 C1 105.28(8) . . ?
C11 P3 C17 109.94(10) . . ?
C11 P3 C5 107.14(10) . . ?
C17 P3 C5 106.90(10) . . ?
C11 P3 C23 109.76(10) . . ?
C17 P3 C23 111.21(10) . . ?
C5 P3 C23 111.77(10) . . ?
O7 C1 C2 107.82(15) . . ?
O7 C1 P1 110.22(12) . . ?
C2 C1 P1 111.34(13) . . ?
O7 C1 P2 109.12(12) . . ?
C2 C1 P2 108.26(12) . . ?
P1 C1 P2 110.00(10) . . ?
C3 C2 C1 115.19(15) . . ?
C4 C3 C2 109.25(15) . . ?
N1 C4 C3 111.11(15) . . ?
C6 C5 C10 119.8(2) . . ?
C6 C5 P3 120.13(16) . . ?
C10 C5 P3 119.60(17) . . ?
C7 C6 C5 119.8(2) . . ?
C6 C7 C8 120.1(2) . . ?
C9 C8 C7 119.8(2) . . ?
C10 C9 C8 120.6(2) . . ?
C9 C10 C5 119.8(2) . . ?
C16 C11 C12 120.0(2) . . ?
C16 C11 P3 121.41(17) . . ?
C12 C11 P3 118.59(16) . . ?
C13 C12 C11 119.9(2) . . ?
C12 C13 C14 120.1(2) . . ?
C15 C14 C13 120.3(2) . . ?
C14 C15 C16 120.3(2) . . ?
C15 C16 C11 119.4(2) . . ?
C18 C17 C22 119.8(2) . . ?
C18 C17 P3 120.97(17) . . ?
C22 C17 P3 119.22(16) . . ?
C17 C18 C19 120.1(2) . . ?
C20 C19 C18 120.0(2) . . ?
C19 C20 C21 120.3(2) . . ?
C22 C21 C20 120.0(2) . . ?
C21 C22 C17 119.9(2) . . ?
C24 C23 P3 115.28(14) . . ?
C25 C24 C29 118.9(2) . . ?
C25 C24 C23 119.9(2) . . ?
C29 C24 C23 121.1(2) . . ?
C26 C25 C24 120.4(2) . . ?
C27 C26 C25 120.3(2) . . ?
C28 C27 C26 119.8(2) . . ?
C27 C28 C29 120.2(2) . . ?
C28 C29 C24 120.4(2) . . ?
N2 C30 C31 179.7(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A O4 0.95(5) 1.62(5) 2.543(2) 164(4) . yes
O6 H6A O3 0.98(5) 1.57(5) 2.554(2) 178(4) 2_746 yes
O7 H7A O8 0.84(4) 2.17(4) 2.958(2) 156(3) 2_756 yes
O8 H8A O5 0.81(4) 2.02(4) 2.822(2) 174(3) . yes
O8 H8B O1 0.91(5) 2.10(5) 2.997(2) 170(4) 1_545 yes
N1 H1N O5 0.89(3) 1.96(3) 2.839(2) 169(3) 3_766 yes
N1 H2N O2 0.91(3) 1.84(3) 2.733(2) 166(3) 3_776 yes
N1 H3N O3 0.90(3) 1.98(3) 2.815(2) 154(3) 4_575 yes

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.073

