# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2020

####################################################################### 
# 
# 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_AP1
_audit_block_doi                 10.5517/ccdc.csd.cc247b6y
_database_code_depnum_ccdc_archive 'CCDC 1973249'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9PP00457B 2020
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Sud Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-01-23 downloaded from the CCDC.
;
#cu_v957_GuillotICMMO PPSM

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H24 N O4 P'
_chemical_formula_sum            'C23 H24 N O4 P'
_chemical_melting_point          ?


_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         409.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0179 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 0.0181 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0495 0.0323 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2958 0.4342 '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'
_chemical_absolute_configuration .

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'

_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.
;

_cell_length_a                   14.1914(5)
_cell_length_b                   9.0659(3)
_cell_length_c                   16.0033(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.488(2)
_cell_angle_gamma                90
_cell_volume                     2017.70(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      65.28

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    1.458
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8324
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_process_details   'Bruker APEX3'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20695
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.178
_diffrn_reflns_theta_max         65.304
_diffrn_reflns_theta_full        65.304
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3458
_reflns_number_gt                2759
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_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)+(0.0375P)²+2.5718P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3458
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0603(2) 0.2933(3) 0.63013(18) 0.0323(6) Uani 1 1 d . . . . .
H1 H 1.120431 0.275730 0.667137 0.039 Uiso 1 1 calc R U . . .
C2 C 1.0161(2) 0.1815(3) 0.57921(18) 0.0342(7) Uani 1 1 d . . . . .
H2 H 1.045892 0.087335 0.581607 0.041 Uiso 1 1 calc R U . . .
C3 C 0.9291(2) 0.2038(3) 0.52458(18) 0.0310(6) Uani 1 1 d . . . . .
H3 H 0.899885 0.124967 0.489692 0.037 Uiso 1 1 calc R U . . .
C4 C 0.88298(18) 0.3412(3) 0.51978(16) 0.0251(6) Uani 1 1 d . . . . .
C5 C 0.79317(18) 0.3686(3) 0.46257(17) 0.0255(6) Uani 1 1 d . . . . .
H5 H 0.763367 0.291655 0.426445 0.031 Uiso 1 1 calc R U . . .
C6 C 0.75018(18) 0.5026(3) 0.45927(16) 0.0252(6) Uani 1 1 d . . . . .
H6 H 0.690719 0.517678 0.420821 0.030 Uiso 1 1 calc R U . . .
C7 C 0.79267(17) 0.6228(3) 0.51277(15) 0.0215(5) Uani 1 1 d . . . . .
C8 C 0.88244(17) 0.5974(3) 0.56886(15) 0.0226(5) Uani 1 1 d . . . . .
C9 C 0.92753(18) 0.4569(3) 0.57252(15) 0.0235(5) Uani 1 1 d . . . . .
C10 C 1.01805(18) 0.4324(3) 0.62819(16) 0.0259(6) Uani 1 1 d . . . . .
C11 C 1.06107(19) 0.5522(3) 0.68060(17) 0.0301(6) Uani 1 1 d . . . . .
H11 H 1.121239 0.537601 0.718085 0.036 Uiso 1 1 calc R U . . .
C12 C 1.01823(18) 0.6849(3) 0.67793(17) 0.0283(6) Uani 1 1 d . . . . .
H12 H 1.048473 0.761435 0.714162 0.034 Uiso 1 1 calc R U . . .
C13 C 0.92828(18) 0.7137(3) 0.62191(16) 0.0240(6) Uani 1 1 d . . . . .
C14 C 0.88578(18) 0.8524(3) 0.61580(16) 0.0266(6) Uani 1 1 d . . . . .
H14 H 0.916097 0.930860 0.650376 0.032 Uiso 1 1 calc R U . . .
C15 C 0.79962(18) 0.8769(3) 0.55971(16) 0.0248(6) Uani 1 1 d . . . . .
H15 H 0.772604 0.973179 0.555338 0.030 Uiso 1 1 calc R U . . .
C16 C 0.75155(17) 0.7644(3) 0.50957(16) 0.0225(5) Uani 1 1 d . . . . .
C17 C 0.65819(17) 0.8035(3) 0.45159(16) 0.0232(5) Uani 1 1 d . . . . .
C18 C 0.48522(17) 0.7585(3) 0.41617(16) 0.0217(5) Uani 1 1 d . . . . .
H18 H 0.489952 0.843552 0.377463 0.026 Uiso 1 1 calc R U . . .
C19 C 0.5317(2) 0.6614(3) 0.22478(17) 0.0353(7) Uani 1 1 d . . . . .
H19A H 0.527935 0.766229 0.241189 0.042 Uiso 1 1 calc R U . . .
H19B H 0.481969 0.643178 0.172943 0.042 Uiso 1 1 calc R U . . .
C20 C 0.6290(2) 0.6282(3) 0.20756(19) 0.0366(7) Uani 1 1 d . . . . .
H20A H 0.640212 0.688213 0.159514 0.055 Uiso 1 1 calc R U . . .
H20B H 0.632891 0.523461 0.193557 0.055 Uiso 1 1 calc R U . . .
H20C H 0.677976 0.651258 0.258296 0.055 Uiso 1 1 calc R U . . .
C21 C 0.25105(19) 0.6295(3) 0.2974(2) 0.0386(7) Uani 1 1 d . . . . .
H21A H 0.251625 0.602699 0.357490 0.046 Uiso 1 1 calc R U . . .
H21B H 0.210588 0.718571 0.283647 0.046 Uiso 1 1 calc R U . . .
C22 C 0.2094(2) 0.5082(3) 0.2418(2) 0.0417(7) Uani 1 1 d . . . . .
H22A H 0.215945 0.529177 0.183117 0.063 Uiso 1 1 calc R U . . .
H22B H 0.141097 0.498037 0.243777 0.063 Uiso 1 1 calc R U . . .
H22C H 0.243103 0.416345 0.261107 0.063 Uiso 1 1 calc R U . . .
C23 C 0.41680(18) 0.8015(3) 0.47460(17) 0.0288(6) Uani 1 1 d . . . . .
H23A H 0.352449 0.818891 0.440300 0.043 Uiso 1 1 calc R U . . .
H23B H 0.440108 0.891705 0.505738 0.043 Uiso 1 1 calc R U . . .
H23C H 0.413927 0.721638 0.515271 0.043 Uiso 1 1 calc R U . . .
N1 N 0.58102(14) 0.7268(2) 0.46456(13) 0.0222(5) Uani 1 1 d . . . . .
H10 H 0.588812 0.656170 0.503054 0.027 Uiso 1 1 calc R U . . .
O1 O 0.65386(13) 0.9032(2) 0.39939(12) 0.0354(5) Uani 1 1 d . . . . .
O2 O 0.51546(12) 0.56601(18) 0.29395(10) 0.0252(4) Uani 1 1 d . . . . .
O3 O 0.34942(12) 0.6626(2) 0.28753(11) 0.0296(4) Uani 1 1 d . . . . .
O4 O 0.42266(13) 0.47043(19) 0.39967(11) 0.0278(4) Uani 1 1 d . . . . .
P1 P 0.44001(4) 0.60028(7) 0.35070(4) 0.02159(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.372(4) . ?
C1 C10 1.394(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.414(4) . ?
C4 C5 1.435(4) . ?
C5 C6 1.356(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.441(3) . ?
C6 H6 0.9500 . ?
C7 C16 1.407(3) . ?
C7 C8 1.423(3) . ?
C8 C9 1.421(3) . ?
C8 C13 1.427(3) . ?
C9 C10 1.428(3) . ?
C10 C11 1.432(4) . ?
C11 C12 1.345(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.430(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.501(3) . ?
C17 O1 1.224(3) . ?
C17 N1 1.348(3) . ?
C18 N1 1.453(3) . ?
C18 C23 1.527(3) . ?
C18 P1 1.816(2) . ?
C18 H18 1.0000 . ?
C19 O2 1.459(3) . ?
C19 C20 1.493(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.463(4) . ?
C21 O3 1.467(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N1 H10 0.8800 . ?
O2 P1 1.5669(18) . ?
O3 P1 1.5739(18) . ?
O4 P1 1.4621(18) . ?

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
C2 C1 C10 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C10 C1 H1 119.6 . . ?
C1 C2 C3 120.9(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C9 118.6(2) . . ?
C3 C4 C5 122.3(2) . . ?
C9 C4 C5 119.1(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C16 C7 C8 118.9(2) . . ?
C16 C7 C6 123.1(2) . . ?
C8 C7 C6 117.9(2) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 C13 119.3(2) . . ?
C7 C8 C13 120.0(2) . . ?
C4 C9 C8 119.7(2) . . ?
C4 C9 C10 119.8(2) . . ?
C8 C9 C10 120.5(2) . . ?
C1 C10 C9 119.0(2) . . ?
C1 C10 C11 122.8(2) . . ?
C9 C10 C11 118.2(2) . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 121.7(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C8 119.1(2) . . ?
C14 C13 C12 122.0(2) . . ?
C8 C13 C12 118.8(2) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 121.7(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C7 119.8(2) . . ?
C15 C16 C17 117.0(2) . . ?
C7 C16 C17 123.2(2) . . ?
O1 C17 N1 123.7(2) . . ?
O1 C17 C16 121.0(2) . . ?
N1 C17 C16 115.3(2) . . ?
N1 C18 C23 111.5(2) . . ?
N1 C18 P1 109.69(16) . . ?
C23 C18 P1 111.14(17) . . ?
N1 C18 H18 108.1 . . ?
C23 C18 H18 108.1 . . ?
P1 C18 H18 108.1 . . ?
O2 C19 C20 108.2(2) . . ?
O2 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
O2 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 O3 111.5(2) . . ?
C22 C21 H21A 109.3 . . ?
O3 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
O3 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 N1 C18 121.2(2) . . ?
C17 N1 H10 119.4 . . ?
C18 N1 H10 119.4 . . ?
C19 O2 P1 123.47(16) . . ?
C21 O3 P1 122.02(17) . . ?
O4 P1 O2 111.01(10) . . ?
O4 P1 O3 115.49(10) . . ?
O2 P1 O3 105.30(10) . . ?
O4 P1 C18 113.86(11) . . ?
O2 P1 C18 106.70(10) . . ?
O3 P1 C18 103.68(11) . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_AP2
_audit_block_doi                 10.5517/ccdc.csd.cc247b7z
_database_code_depnum_ccdc_archive 'CCDC 1973250'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9PP00457B 2020
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Sud Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H28 N O4 P'
_chemical_formula_sum            'C25 H28 N O4 P'
_chemical_melting_point          ?


_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         437.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0179 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 0.0181 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0495 0.0323 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2958 0.4342 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_chemical_absolute_configuration .

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

_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.
;

_cell_length_a                   26.8408(13)
_cell_length_b                   9.9974(5)
_cell_length_c                   17.4578(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.5060(10)
_cell_angle_gamma                90
_cell_volume                     4387.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      66.64
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.374
_shelx_estimated_absorpt_T_min   0.748
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7302
_exptl_absorpt_correction_T_max  0.8528
_exptl_absorpt_process_details   'Bruker APEX3'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36707
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.516
_diffrn_reflns_theta_max         66.654
_diffrn_reflns_theta_full        66.654
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3865
_reflns_number_gt                3764
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0418P)²+5.1097P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3865
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.86715(6) 0.26326(15) 0.67032(9) 0.0232(3) Uani 1 1 d . . . . .
H1 H 0.900020 0.305007 0.700252 0.028 Uiso 1 1 calc R U . . .
C2 C 0.86599(6) 0.16223(15) 0.61515(9) 0.0243(3) Uani 1 1 d . . . . .
H2 H 0.898030 0.134600 0.608270 0.029 Uiso 1 1 calc R U . . .
C3 C 0.81832(6) 0.10156(14) 0.57009(9) 0.0223(3) Uani 1 1 d . . . . .
H3 H 0.817974 0.032915 0.532284 0.027 Uiso 1 1 calc R U . . .
C4 C 0.77076(5) 0.13989(13) 0.57946(8) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.72046(5) 0.08007(13) 0.53329(8) 0.0193(3) Uani 1 1 d . . . . .
H5 H 0.719141 0.013390 0.493861 0.023 Uiso 1 1 calc R U . . .
C6 C 0.67498(5) 0.11629(13) 0.54457(8) 0.0183(3) Uani 1 1 d . . . . .
H6 H 0.642557 0.073684 0.513480 0.022 Uiso 1 1 calc R U . . .
C7 C 0.67468(5) 0.21804(13) 0.60270(8) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.72382(5) 0.28123(13) 0.64853(8) 0.0154(3) Uani 1 1 d . . . . .
C9 C 0.77165(5) 0.24193(13) 0.63666(8) 0.0165(3) Uani 1 1 d . . . . .
C10 C 0.82077(5) 0.30452(13) 0.68253(8) 0.0190(3) Uani 1 1 d . . . . .
C11 C 0.82075(5) 0.40735(14) 0.74022(8) 0.0208(3) Uani 1 1 d . . . . .
H11 H 0.853196 0.450343 0.770784 0.025 Uiso 1 1 calc R U . . .
C12 C 0.77545(6) 0.44378(14) 0.75165(8) 0.0205(3) Uani 1 1 d . . . . .
H12 H 0.776703 0.511921 0.790207 0.025 Uiso 1 1 calc R U . . .
C13 C 0.72536(5) 0.38190(13) 0.70687(8) 0.0175(3) Uani 1 1 d . . . . .
C14 C 0.67836(6) 0.41768(14) 0.71915(8) 0.0199(3) Uani 1 1 d . . . . .
H14 H 0.679117 0.483188 0.758961 0.024 Uiso 1 1 calc R U . . .
C15 C 0.63065(5) 0.35770(14) 0.67332(8) 0.0195(3) Uani 1 1 d . . . . .
H15 H 0.598858 0.384472 0.681311 0.023 Uiso 1 1 calc R U . . .
C16 C 0.62829(5) 0.25917(13) 0.61587(8) 0.0176(3) Uani 1 1 d . . . . .
C17 C 0.57610(5) 0.19161(13) 0.57152(8) 0.0192(3) Uani 1 1 d . . . . .
C18 C 0.48311(5) 0.22326(13) 0.48393(8) 0.0171(3) Uani 1 1 d . . . . .
H18 H 0.482885 0.127915 0.501123 0.021 Uiso 1 1 calc R U . . .
C19 C 0.42182(7) 0.27779(16) 0.66051(10) 0.0308(4) Uani 1 1 d . . . . .
H19A H 0.394303 0.345925 0.634596 0.037 Uiso 1 1 calc R U . A 1
H19B H 0.444728 0.312066 0.714593 0.037 Uiso 1 1 calc R U . A 1
C20A C 0.3959(5) 0.1504(7) 0.6711(6) 0.0483(16) Uani 0.65(3) 1 d . . P B 1
H20A H 0.372746 0.117601 0.617569 0.072 Uiso 0.65(3) 1 calc R U P B 1
H20B H 0.374567 0.166634 0.705773 0.072 Uiso 0.65(3) 1 calc R U P B 1
H20C H 0.423222 0.083357 0.697052 0.072 Uiso 0.65(3) 1 calc R U P B 1
C21 C 0.33832(5) 0.32066(14) 0.41238(9) 0.0226(3) Uani 1 1 d . . . . .
H21A H 0.339334 0.297160 0.357853 0.027 Uiso 1 1 calc R U . . .
H21B H 0.344031 0.418255 0.420407 0.027 Uiso 1 1 calc R U . . .
C22 C 0.28541(6) 0.28295(15) 0.41741(10) 0.0276(3) Uani 1 1 d . . . . .
H22A H 0.279446 0.186853 0.407223 0.041 Uiso 1 1 calc R U . . .
H22B H 0.257172 0.333111 0.376275 0.041 Uiso 1 1 calc R U . . .
H22C H 0.285087 0.304287 0.472024 0.041 Uiso 1 1 calc R U . . .
C23 C 0.46818(5) 0.22202(14) 0.39014(8) 0.0207(3) Uani 1 1 d . . . . .
H23 H 0.431445 0.184484 0.365869 0.025 Uiso 1 1 calc R U . . .
C24 C 0.50574(6) 0.12821(16) 0.36792(9) 0.0267(3) Uani 1 1 d . . . . .
H24A H 0.495377 0.123475 0.308291 0.040 Uiso 1 1 calc R U . . .
H24B H 0.503780 0.038753 0.389646 0.040 Uiso 1 1 calc R U . . .
H24C H 0.542222 0.162036 0.391528 0.040 Uiso 1 1 calc R U . . .
C25 C 0.46785(6) 0.36060(15) 0.35353(9) 0.0267(3) Uani 1 1 d . . . . .
H25A H 0.458599 0.352852 0.294195 0.040 Uiso 1 1 calc R U . . .
H25B H 0.503194 0.401059 0.377517 0.040 Uiso 1 1 calc R U . . .
H25C H 0.441559 0.416985 0.365343 0.040 Uiso 1 1 calc R U . . .
N1 N 0.53663(4) 0.27427(11) 0.52755(7) 0.0171(2) Uani 1 1 d . . . . .
H10 H 0.543223 0.360088 0.525137 0.021 Uiso 1 1 calc R U . . .
O1 O 0.57074(4) 0.07053(10) 0.57730(7) 0.0275(2) Uani 1 1 d . . . . .
O2 O 0.45371(4) 0.25413(10) 0.60960(6) 0.0258(2) Uani 1 1 d . . . . .
O3 O 0.37989(4) 0.24826(9) 0.47592(6) 0.0223(2) Uani 1 1 d . . . . .
O4 O 0.43648(4) 0.45873(10) 0.51323(6) 0.0222(2) Uani 1 1 d . . . . .
P1 P 0.43667(2) 0.31187(3) 0.52005(2) 0.01725(11) Uani 1 1 d . . . . .
C20B C 0.4205(13) 0.1504(13) 0.7027(17) 0.065(5) Uani 0.35(3) 1 d . . P B 2
H20D H 0.404975 0.080310 0.662105 0.097 Uiso 0.35(3) 1 calc R U P B 2
H20E H 0.398848 0.161425 0.737339 0.097 Uiso 0.35(3) 1 calc R U P B 2
H20F H 0.456770 0.124949 0.736761 0.097 Uiso 0.35(3) 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.388(2) . ?
C1 C10 1.397(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C9 1.4218(19) . ?
C4 C5 1.4380(19) . ?
C5 C6 1.352(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.4388(19) . ?
C6 H6 0.9500 . ?
C7 C16 1.4048(19) . ?
C7 C8 1.4281(18) . ?
C8 C13 1.4222(19) . ?
C8 C9 1.4255(19) . ?
C9 C10 1.4251(19) . ?
C10 C11 1.439(2) . ?
C11 C12 1.349(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.4371(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3981(19) . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.5026(18) . ?
C17 O1 1.2273(17) . ?
C17 N1 1.3510(18) . ?
C18 N1 1.4619(16) . ?
C18 C23 1.5434(18) . ?
C18 P1 1.8129(13) . ?
C18 H18 1.0000 . ?
C19 O2 1.4532(17) . ?
C19 C20B 1.478(13) . ?
C19 C20A 1.494(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C21 O3 1.4602(17) . ?
C21 C22 1.501(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.523(2) . ?
C23 C25 1.524(2) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 H10 0.8800 . ?
O2 P1 1.5766(10) . ?
O3 P1 1.5806(10) . ?
O4 P1 1.4728(10) . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?

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
C2 C1 C10 121.07(13) . . ?
C2 C1 H1 119.5 . . ?
C10 C1 H1 119.5 . . ?
C3 C2 C1 120.28(13) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.93(13) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C9 119.21(13) . . ?
C3 C4 C5 122.53(13) . . ?
C9 C4 C5 118.27(12) . . ?
C6 C5 C4 121.69(12) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 121.36(12) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C16 C7 C8 118.45(12) . . ?
C16 C7 C6 123.14(12) . . ?
C8 C7 C6 118.40(12) . . ?
C13 C8 C9 119.84(12) . . ?
C13 C8 C7 120.24(12) . . ?
C9 C8 C7 119.91(12) . . ?
C4 C9 C10 119.63(12) . . ?
C4 C9 C8 120.36(12) . . ?
C10 C9 C8 120.01(12) . . ?
C1 C10 C9 118.88(13) . . ?
C1 C10 C11 122.44(13) . . ?
C9 C10 C11 118.67(12) . . ?
C12 C11 C10 121.17(12) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 121.55(13) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C8 119.31(12) . . ?
C14 C13 C12 121.94(12) . . ?
C8 C13 C12 118.75(12) . . ?
C15 C14 C13 120.10(12) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 121.46(12) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C7 120.41(12) . . ?
C15 C16 C17 119.25(12) . . ?
C7 C16 C17 120.25(12) . . ?
O1 C17 N1 123.98(12) . . ?
O1 C17 C16 121.06(12) . . ?
N1 C17 C16 114.95(11) . . ?
N1 C18 C23 113.45(10) . . ?
N1 C18 P1 108.55(9) . . ?
C23 C18 P1 114.74(9) . . ?
N1 C18 H18 106.5 . . ?
C23 C18 H18 106.5 . . ?
P1 C18 H18 106.5 . . ?
O2 C19 C20B 106.7(5) . . ?
O2 C19 C20A 109.7(3) . . ?
O2 C19 H19A 109.7 . . ?
C20A C19 H19A 109.7 . . ?
O2 C19 H19B 109.7 . . ?
C20A C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20A H20A 109.5 . . ?
C19 C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19 C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
O3 C21 C22 108.53(11) . . ?
O3 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
O3 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C25 111.10(12) . . ?
C24 C23 C18 109.03(11) . . ?
C25 C23 C18 113.50(11) . . ?
C24 C23 H23 107.7 . . ?
C25 C23 H23 107.7 . . ?
C18 C23 H23 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C17 N1 C18 120.97(11) . . ?
C17 N1 H10 119.5 . . ?
C18 N1 H10 119.5 . . ?
C19 O2 P1 121.23(10) . . ?
C21 O3 P1 121.37(8) . . ?
O4 P1 O2 115.90(6) . . ?
O4 P1 O3 112.72(5) . . ?
O2 P1 O3 103.37(6) . . ?
O4 P1 C18 116.26(6) . . ?
O2 P1 C18 99.79(6) . . ?
O3 P1 C18 107.27(6) . . ?
C19 C20B H20D 109.5 . . ?
C19 C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19 C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_AP3
_audit_block_doi                 10.5517/ccdc.csd.cc247b80
_database_code_depnum_ccdc_archive 'CCDC 1973251'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9PP00457B 2020
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Sud Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C28 H26 N O4 P'
_chemical_formula_sum            'C28 H26 N O4 P'
_chemical_melting_point          ?


_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         471.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0179 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 0.0181 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0495 0.0323 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2958 0.4342 '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'
_chemical_absolute_configuration .

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

_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.
;

_cell_length_a                   9.7414(5)
_cell_length_b                   10.2898(5)
_cell_length_c                   13.4571(6)
_cell_angle_alpha                110.2840(10)
_cell_angle_beta                 109.5130(10)
_cell_angle_gamma                90.7320(10)
_cell_volume                     1179.90(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9781
_cell_measurement_theta_min      4.63
_cell_measurement_theta_max      66.72

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.323
_shelx_estimated_absorpt_T_min   0.756
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8391
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_process_details   'Bruker APEX3'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29926
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.755
_diffrn_reflns_theta_max         66.716
_diffrn_reflns_theta_full        66.716
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4175
_reflns_number_gt                4071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_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)+(0.0493P)²+0.7975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4175
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8332(2) 0.64437(19) 1.27000(14) 0.0304(4) Uani 1 1 d . . . . .
H1 H 0.895715 0.644072 1.341257 0.036 Uiso 1 1 calc R U . . .
C2 C 0.7317(2) 0.73690(19) 1.26673(15) 0.0312(4) Uani 1 1 d . . . . .
H2 H 0.725019 0.799157 1.335575 0.037 Uiso 1 1 calc R U . . .
C3 C 0.63964(19) 0.73961(18) 1.16401(15) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.570317 0.803689 1.162878 0.034 Uiso 1 1 calc R U . . .
C4 C 0.64791(17) 0.64876(16) 1.06187(13) 0.0216(3) Uani 1 1 d . . . . .
C5 C 0.55337(18) 0.64741(17) 0.95340(14) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.482395 0.709817 0.950639 0.029 Uiso 1 1 calc R U . . .
C6 C 0.56292(17) 0.55977(16) 0.85546(13) 0.0209(3) Uani 1 1 d . . . . .
H6 H 0.499294 0.562475 0.785384 0.025 Uiso 1 1 calc R U . . .
C7 C 0.66736(16) 0.46236(15) 0.85492(13) 0.0172(3) Uani 1 1 d . . . . .
C8 C 0.76125(16) 0.45936(15) 0.96104(13) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.75133(17) 0.55311(16) 1.06402(13) 0.0200(3) Uani 1 1 d . . . . .
C10 C 0.84528(18) 0.55136(17) 1.17031(14) 0.0243(4) Uani 1 1 d . . . . .
C11 C 0.9502(2) 0.45458(18) 1.17013(14) 0.0294(4) Uani 1 1 d . . . . .
H11 H 1.014341 0.453180 1.240531 0.035 Uiso 1 1 calc R U . . .
C12 C 0.96023(19) 0.36564(18) 1.07285(15) 0.0283(4) Uani 1 1 d . . . . .
H12 H 1.031095 0.303155 1.076194 0.034 Uiso 1 1 calc R U . . .
C13 C 0.86529(17) 0.36360(16) 0.96370(14) 0.0221(3) Uani 1 1 d . . . . .
C14 C 0.87317(18) 0.27267(17) 0.86207(14) 0.0254(4) Uani 1 1 d . . . . .
H14 H 0.943254 0.209327 0.863355 0.030 Uiso 1 1 calc R U . . .
C15 C 0.77966(17) 0.27372(16) 0.75901(14) 0.0219(3) Uani 1 1 d . . . . .
H15 H 0.784923 0.209425 0.690356 0.026 Uiso 1 1 calc R U . . .
C16 C 0.67802(16) 0.36760(15) 0.75447(13) 0.0175(3) Uani 1 1 d . . . . .
C17 C 0.58670(16) 0.37131(15) 0.64122(12) 0.0170(3) Uani 1 1 d . . . . .
C18 C 0.42065(16) 0.23435(15) 0.44738(12) 0.0157(3) Uani 1 1 d . . . . .
H18 H 0.429569 0.328542 0.442251 0.019 Uiso 1 1 calc R U . . .
C19 C 0.69247(18) 0.32371(17) 0.37841(15) 0.0260(4) Uani 1 1 d . . . . .
H19A H 0.609075 0.376914 0.381673 0.031 Uiso 1 1 calc R U . . .
H19B H 0.701872 0.304499 0.303791 0.031 Uiso 1 1 calc R U . . .
C20 C 0.8312(2) 0.4065(2) 0.47184(18) 0.0386(5) Uani 1 1 d . . . . .
H20A H 0.819892 0.427128 0.545222 0.058 Uiso 1 1 calc R U . . .
H20B H 0.852108 0.494420 0.462968 0.058 Uiso 1 1 calc R U . . .
H20C H 0.912730 0.352363 0.468690 0.058 Uiso 1 1 calc R U . . .
C23 C 0.25823(16) 0.17899(15) 0.40497(12) 0.0163(3) Uani 1 1 d . . . . .
C24 C 0.20772(17) 0.07271(15) 0.43161(12) 0.0188(3) Uani 1 1 d . . . . .
H24 H 0.275200 0.037279 0.481865 0.023 Uiso 1 1 calc R U . . .
C25 C 0.05911(18) 0.01829(16) 0.38501(14) 0.0227(3) Uani 1 1 d . . . . .
H25 H 0.025486 -0.053497 0.404211 0.027 Uiso 1 1 calc R U . . .
C26 C -0.04051(17) 0.06814(17) 0.31060(15) 0.0259(4) Uani 1 1 d . . . . .
H26 H -0.141861 0.030057 0.278171 0.031 Uiso 1 1 calc R U . . .
C27 C 0.00939(18) 0.17416(18) 0.28402(14) 0.0259(4) Uani 1 1 d . . . . .
H27 H -0.058354 0.209016 0.233453 0.031 Uiso 1 1 calc R U . . .
C28 C 0.15748(17) 0.22964(16) 0.33076(13) 0.0212(3) Uani 1 1 d . . . . .
H28 H 0.190461 0.302360 0.312201 0.025 Uiso 1 1 calc R U . . .
N1 N 0.50488(13) 0.24876(13) 0.56400(10) 0.0163(3) Uani 1 1 d . . . . .
H1A H 0.502186 0.176327 0.584176 0.020 Uiso 1 1 calc R U . . .
O1 O 0.59018(13) 0.47912(11) 0.62109(9) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.66625(11) 0.19231(11) 0.39264(9) 0.0206(2) Uani 1 1 d . . . . .
O3 O 0.42101(12) 0.12356(11) 0.23498(9) 0.0226(3) Uani 1 1 d . . . . .
O4 O 0.50755(12) -0.02231(11) 0.36023(9) 0.0204(2) Uani 1 1 d . . . . .
P1 P 0.50545(4) 0.11821(4) 0.35531(3) 0.01488(12) Uani 1 1 d . . . . .
C21A C 0.3766(7) 0.0137(5) 0.1277(5) 0.0419(7) Uani 0.425(4) 1 d . . P A 1
H21A H 0.470549 -0.017496 0.122653 0.050 Uiso 0.425(4) 1 calc R U P A 1
H21B H 0.326686 -0.061849 0.138730 0.050 Uiso 0.425(4) 1 calc R U P A 1
C22A C 0.3067(7) 0.0009(5) 0.0337(4) 0.0419(7) Uani 0.425(4) 1 d . . P A 1
H22A H 0.277106 0.091098 0.032342 0.063 Uiso 0.425(4) 1 calc R U P A 1
H22B H 0.218778 -0.068302 0.004472 0.063 Uiso 0.425(4) 1 calc R U P A 1
H22C H 0.366162 -0.030812 -0.013932 0.063 Uiso 0.425(4) 1 calc R U P A 1
C21B C 0.3146(5) 0.0075(4) 0.1445(3) 0.0419(7) Uani 0.575(4) 1 d . . P A 2
H21C H 0.367075 -0.072356 0.120084 0.050 Uiso 0.575(4) 1 calc R U P A 2
H21D H 0.245254 -0.022087 0.174800 0.050 Uiso 0.575(4) 1 calc R U P A 2
C22B C 0.2334(5) 0.0377(4) 0.0490(3) 0.0419(7) Uani 0.575(4) 1 d . . P A 2
H22D H 0.138497 0.062646 0.054018 0.063 Uiso 0.575(4) 1 calc R U P A 2
H22E H 0.216662 -0.044755 -0.020123 0.063 Uiso 0.575(4) 1 calc R U P A 2
H22F H 0.288422 0.116308 0.046686 0.063 Uiso 0.575(4) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(3) . ?
C1 C10 1.396(2) . ?
C2 C3 1.384(3) . ?
C3 C4 1.398(2) . ?
C4 C9 1.418(2) . ?
C4 C5 1.438(2) . ?
C5 C6 1.349(2) . ?
C6 C7 1.437(2) . ?
C7 C16 1.404(2) . ?
C7 C8 1.427(2) . ?
C8 C13 1.423(2) . ?
C8 C9 1.423(2) . ?
C9 C10 1.424(2) . ?
C10 C11 1.436(3) . ?
C11 C12 1.348(3) . ?
C12 C13 1.444(2) . ?
C13 C14 1.392(2) . ?
C14 C15 1.386(2) . ?
C15 C16 1.394(2) . ?
C16 C17 1.500(2) . ?
C17 O1 1.2323(18) . ?
C17 N1 1.348(2) . ?
C18 N1 1.4606(18) . ?
C18 C23 1.517(2) . ?
C18 P1 1.8243(15) . ?
C19 O2 1.4607(18) . ?
C19 C20 1.492(2) . ?
C23 C24 1.394(2) . ?
C23 C28 1.397(2) . ?
C24 C25 1.390(2) . ?
C25 C26 1.388(2) . ?
C26 C27 1.388(2) . ?
C27 C28 1.388(2) . ?
O2 P1 1.5702(11) . ?
O3 C21A 1.410(5) . ?
O3 C21B 1.449(4) . ?
O3 P1 1.5731(11) . ?
O4 P1 1.4703(11) . ?
C21A C22A 1.178(7) . ?
C21B C22B 1.406(5) . ?

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
C2 C1 C10 121.07(16) . . ?
C1 C2 C3 120.54(16) . . ?
C2 C3 C4 120.50(16) . . ?
C3 C4 C9 119.52(15) . . ?
C3 C4 C5 122.20(15) . . ?
C9 C4 C5 118.28(14) . . ?
C6 C5 C4 121.65(15) . . ?
C5 C6 C7 121.37(14) . . ?
C16 C7 C8 118.71(14) . . ?
C16 C7 C6 122.84(14) . . ?
C8 C7 C6 118.43(14) . . ?
C13 C8 C9 120.21(14) . . ?
C13 C8 C7 119.97(14) . . ?
C9 C8 C7 119.81(14) . . ?
C4 C9 C8 120.45(14) . . ?
C4 C9 C10 119.39(15) . . ?
C8 C9 C10 120.15(15) . . ?
C1 C10 C9 118.97(16) . . ?
C1 C10 C11 122.78(16) . . ?
C9 C10 C11 118.25(15) . . ?
C12 C11 C10 121.86(15) . . ?
C11 C12 C13 121.21(16) . . ?
C14 C13 C8 119.34(14) . . ?
C14 C13 C12 122.36(15) . . ?
C8 C13 C12 118.30(15) . . ?
C15 C14 C13 120.57(14) . . ?
C14 C15 C16 121.04(15) . . ?
C15 C16 C7 120.35(14) . . ?
C15 C16 C17 118.92(13) . . ?
C7 C16 C17 120.63(13) . . ?
O1 C17 N1 123.28(14) . . ?
O1 C17 C16 121.43(13) . . ?
N1 C17 C16 115.27(12) . . ?
N1 C18 C23 115.22(12) . . ?
N1 C18 P1 107.75(10) . . ?
C23 C18 P1 109.32(10) . . ?
O2 C19 C20 108.09(14) . . ?
C24 C23 C28 119.06(14) . . ?
C24 C23 C18 122.02(13) . . ?
C28 C23 C18 118.78(13) . . ?
C25 C24 C23 120.33(14) . . ?
C26 C25 C24 120.45(15) . . ?
C25 C26 C27 119.37(15) . . ?
C28 C27 C26 120.52(15) . . ?
C27 C28 C23 120.27(15) . . ?
C17 N1 C18 121.02(12) . . ?
C19 O2 P1 120.90(9) . . ?
C21A O3 P1 128.5(2) . . ?
C21B O3 P1 121.89(18) . . ?
O4 P1 O2 110.60(6) . . ?
O4 P1 O3 115.68(6) . . ?
O2 P1 O3 105.24(6) . . ?
O4 P1 C18 113.63(6) . . ?
O2 P1 C18 106.67(6) . . ?
O3 P1 C18 104.26(6) . . ?
C22A C21A O3 135.6(5) . . ?
C22B C21B O3 114.3(3) . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.056

