# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 
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data_3_1821116
_database_code_depnum_ccdc_archive 'CCDC 1821116'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H37 N2 O2 P'
_chemical_formula_sum            'C24 H37 N2 O2 P'
_chemical_formula_weight         416.52

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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'

_cell_length_a                   19.931(8)
_cell_length_b                   12.616(8)
_cell_length_c                   21.565(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.346(14)
_cell_angle_gamma                90
_cell_volume                     5116(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    213
_cell_measurement_reflns_used    9023
_cell_measurement_theta_min      2.414
_cell_measurement_theta_max      28.379

_exptl_crystal_description       cubical
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   0.9849
_diffrn_ambient_temperature      213
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18786
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.944
_diffrn_reflns_theta_max         28.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6358
_reflns_number_gt                5265
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0873P)²+1.5364P] 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         6358
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.28217(7) 0.50490(10) 0.36296(6) 0.0409(3) Uani 1 1 d . . . . .
C2 C 0.25359(8) 0.56944(12) 0.40138(7) 0.0472(3) Uani 1 1 d . . . . .
C5 C 0.15455(14) 0.6754(2) 0.32512(16) 0.1083(10) Uani 1 1 d . . . . .
H5A H 0.179923 0.739989 0.340836 0.162 Uiso 1 1 calc R U . . .
H5B H 0.104329 0.688554 0.311874 0.162 Uiso 1 1 calc R U . . .
H5C H 0.166538 0.649626 0.288221 0.162 Uiso 1 1 calc R U . . .
C3 C 0.17484(9) 0.59321(14) 0.37944(9) 0.0564(4) Uani 1 1 d . . . . .
H3 H 0.150468 0.527573 0.360186 0.068 Uiso 1 1 calc R U . . .
C4 C 0.14650(14) 0.6235(2) 0.43460(13) 0.0921(8) Uani 1 1 d . . . . .
H4A H 0.169459 0.687171 0.455484 0.138 Uiso 1 1 calc R U . . .
H4B H 0.156060 0.567211 0.466320 0.138 Uiso 1 1 calc R U . . .
H4C H 0.096122 0.635077 0.416721 0.138 Uiso 1 1 calc R U . . .
C6 C 0.30027(11) 0.61273(15) 0.45880(8) 0.0627(5) Uani 1 1 d . . . . .
H6 H 0.282300 0.654871 0.485021 0.075 Uiso 1 1 calc R U . . .
C7 C 0.37210(11) 0.59489(17) 0.47776(9) 0.0722(6) Uani 1 1 d . . . . .
H7 H 0.402229 0.624654 0.516414 0.087 Uiso 1 1 calc R U . . .
C8 C 0.39947(10) 0.53286(16) 0.43944(9) 0.0656(5) Uani 1 1 d . . . . .
H8 H 0.448264 0.521163 0.452688 0.079 Uiso 1 1 calc R U . . .
C9 C 0.35570(8) 0.48702(12) 0.38109(8) 0.0514(4) Uani 1 1 d . . . . .
C10 C 0.38652(10) 0.41965(16) 0.33875(11) 0.0678(5) Uani 1 1 d . . . . .
H10 H 0.348747 0.408531 0.296559 0.081 Uiso 1 1 calc R U . . .
C12 C 0.40932(17) 0.3111(2) 0.36915(18) 0.1121(10) Uani 1 1 d . . . . .
H12A H 0.445278 0.319367 0.411384 0.168 Uiso 1 1 calc R U . . .
H12B H 0.428058 0.270312 0.341031 0.168 Uiso 1 1 calc R U . . .
H12C H 0.369024 0.275063 0.374208 0.168 Uiso 1 1 calc R U . . .
C11 C 0.44753(16) 0.4753(2) 0.32458(17) 0.1126(10) Uani 1 1 d . . . . .
H11A H 0.431867 0.543354 0.305276 0.169 Uiso 1 1 calc R U . . .
H11B H 0.462858 0.433226 0.294674 0.169 Uiso 1 1 calc R U . . .
H11C H 0.486391 0.484487 0.364841 0.169 Uiso 1 1 calc R U . . .
C13 C 0.15130(7) 0.27153(11) 0.17379(6) 0.0393(3) Uani 1 1 d . . . . .
H13 H 0.149488 0.228268 0.138355 0.047 Uiso 1 1 calc R U . . .
C14 C 0.10147(7) 0.34200(10) 0.17242(6) 0.0370(3) Uani 1 1 d . . . . .
C15 C 0.03587(7) 0.37877(12) 0.11962(7) 0.0436(3) Uani 1 1 d . . . . .
C16 C -0.02688(8) 0.37328(16) 0.14534(9) 0.0613(4) Uani 1 1 d . . . . .
H16A H -0.030553 0.302854 0.160776 0.092 Uiso 1 1 calc R U . . .
H16B H -0.069942 0.390849 0.110574 0.092 Uiso 1 1 calc R U . . .
H16C H -0.019553 0.422680 0.180838 0.092 Uiso 1 1 calc R U . . .
C17 C 0.04605(11) 0.49326(15) 0.10067(11) 0.0705(5) Uani 1 1 d . . . . .
H17A H 0.055429 0.538055 0.138590 0.106 Uiso 1 1 calc R U . . .
H17B H 0.003668 0.516954 0.067111 0.106 Uiso 1 1 calc R U . . .
H17C H 0.085418 0.496473 0.084456 0.106 Uiso 1 1 calc R U . . .
C18 C 0.02117(10) 0.30669(17) 0.05969(8) 0.0694(5) Uani 1 1 d . . . . .
H18A H 0.060907 0.308813 0.043946 0.104 Uiso 1 1 calc R U . . .
H18B H -0.020796 0.330609 0.025706 0.104 Uiso 1 1 calc R U . . .
H18C H 0.014150 0.235341 0.071758 0.104 Uiso 1 1 calc R U . . .
C19 C 0.21760(7) 0.17328(11) 0.27374(7) 0.0419(3) Uani 1 1 d . . . . .
H19 H 0.230098 0.108714 0.259843 0.050 Uiso 1 1 calc R U . . .
C20 C 0.20674(7) 0.18571(10) 0.33051(7) 0.0409(3) Uani 1 1 d . . . . .
C21 C 0.21392(10) 0.11227(13) 0.38707(8) 0.0539(4) Uani 1 1 d . . . . .
C22 C 0.14656(13) 0.1183(2) 0.40568(14) 0.0929(8) Uani 1 1 d . . . . .
H22A H 0.138745 0.190213 0.416064 0.139 Uiso 1 1 calc R U . . .
H22B H 0.151833 0.074052 0.443231 0.139 Uiso 1 1 calc R U . . .
H22C H 0.106713 0.094284 0.369447 0.139 Uiso 1 1 calc R U . . .
C24 C 0.22712(15) -0.00066(14) 0.36670(10) 0.0813(6) Uani 1 1 d . . . . .
H24A H 0.186774 -0.023514 0.330575 0.122 Uiso 1 1 calc R U . . .
H24B H 0.234086 -0.047938 0.403183 0.122 Uiso 1 1 calc R U . . .
H24C H 0.268721 -0.000959 0.353645 0.122 Uiso 1 1 calc R U . . .
C23 C 0.27757(13) 0.14619(17) 0.44605(9) 0.0742(6) Uani 1 1 d . . . . .
H23A H 0.320763 0.133359 0.436770 0.111 Uiso 1 1 calc R U . . .
H23B H 0.278040 0.106141 0.484048 0.111 Uiso 1 1 calc R U . . .
H23C H 0.273835 0.220346 0.454345 0.111 Uiso 1 1 calc R U . . .
N2 N 0.20832(6) 0.26874(9) 0.23546(5) 0.0378(2) Uani 1 1 d . . . . .
N1 N 0.23632(7) 0.46489(9) 0.30352(6) 0.0450(3) Uani 1 1 d . . . . .
O1 O 0.18717(5) 0.29158(7) 0.34086(5) 0.0408(2) Uani 1 1 d . . . . .
O2 O 0.11558(5) 0.39773(8) 0.23237(5) 0.0410(2) Uani 1 1 d . . . . .
P1 P 0.19197(2) 0.36628(2) 0.28227(2) 0.03317(11) 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 N1 1.3988(18) . ?
C1 C9 1.404(2) . ?
C1 C2 1.409(2) . ?
C2 C6 1.391(2) . ?
C2 C3 1.512(2) . ?
C5 C3 1.516(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C3 C4 1.525(3) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C7 1.371(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.518(3) . ?
C10 C11 1.520(3) . ?
C10 C12 1.521(3) . ?
C10 H10 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.3259(19) . ?
C13 N2 1.4352(18) . ?
C13 H13 0.9300 . ?
C14 O2 1.4157(16) . ?
C14 C15 1.4950(19) . ?
C15 C18 1.527(2) . ?
C15 C16 1.528(2) . ?
C15 C17 1.533(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.321(2) . ?
C19 N2 1.4370(19) . ?
C19 H19 0.9300 . ?
C20 O1 1.4294(17) . ?
C20 C21 1.500(2) . ?
C21 C22 1.525(3) . ?
C21 C23 1.530(3) . ?
C21 C24 1.539(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N2 P1 1.6903(13) . ?
N1 P1 1.5069(14) . ?
O1 P1 1.6044(12) . ?
O2 P1 1.5962(11) . ?

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
N1 C1 C9 120.12(14) . . ?
N1 C1 C2 118.60(13) . . ?
C9 C1 C2 121.12(13) . . ?
C6 C2 C1 117.96(16) . . ?
C6 C2 C3 121.31(16) . . ?
C1 C2 C3 120.70(13) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C3 C5 111.17(14) . . ?
C2 C3 C4 114.84(17) . . ?
C5 C3 C4 111.0(2) . . ?
C2 C3 H3 106.4 . . ?
C5 C3 H3 106.4 . . ?
C4 C3 H3 106.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C6 C2 121.70(19) . . ?
C7 C6 H6 119.1 . . ?
C2 C6 H6 119.1 . . ?
C6 C7 C8 119.81(16) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 121.54(17) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C1 117.84(17) . . ?
C8 C9 C10 121.14(17) . . ?
C1 C9 C10 121.02(14) . . ?
C9 C10 C11 111.85(19) . . ?
C9 C10 C12 111.56(19) . . ?
C11 C10 C12 111.0(2) . . ?
C9 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C12 C10 H10 107.4 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C13 N2 113.23(11) . . ?
C14 C13 H13 123.4 . . ?
N2 C13 H13 123.4 . . ?
C13 C14 O2 113.07(12) . . ?
C13 C14 C15 133.22(12) . . ?
O2 C14 C15 113.61(11) . . ?
C14 C15 C18 109.51(12) . . ?
C14 C15 C16 108.90(13) . . ?
C18 C15 C16 109.24(14) . . ?
C14 C15 C17 109.62(13) . . ?
C18 C15 C17 109.92(15) . . ?
C16 C15 C17 109.63(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 N2 113.80(12) . . ?
C20 C19 H19 123.1 . . ?
N2 C19 H19 123.1 . . ?
C19 C20 O1 113.10(12) . . ?
C19 C20 C21 132.78(13) . . ?
O1 C20 C21 114.05(12) . . ?
C20 C21 C22 109.15(14) . . ?
C20 C21 C23 109.43(15) . . ?
C22 C21 C23 109.09(18) . . ?
C20 C21 C24 108.60(14) . . ?
C22 C21 C24 111.69(18) . . ?
C23 C21 C24 108.85(16) . . ?
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 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 N2 C19 117.69(11) . . ?
C13 N2 P1 106.58(9) . . ?
C19 N2 P1 106.29(9) . . ?
C1 N1 P1 135.72(10) . . ?
C20 O1 P1 109.60(8) . . ?
C14 O2 P1 110.41(8) . . ?
N1 P1 O2 109.40(7) . . ?
N1 P1 O1 115.30(7) . . ?
O2 P1 O1 112.62(6) . . ?
N1 P1 N2 124.96(7) . . ?
O2 P1 N2 96.19(6) . . ?
O1 P1 N2 96.68(7) . . ?

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
N1 C1 C2 C6 -177.03(13) . . . . ?
C9 C1 C2 C6 -1.7(2) . . . . ?
N1 C1 C2 C3 1.15(19) . . . . ?
C9 C1 C2 C3 176.52(13) . . . . ?
C6 C2 C3 C5 101.6(2) . . . . ?
C1 C2 C3 C5 -76.5(2) . . . . ?
C6 C2 C3 C4 -25.5(2) . . . . ?
C1 C2 C3 C4 156.40(16) . . . . ?
C1 C2 C6 C7 0.7(2) . . . . ?
C3 C2 C6 C7 -177.45(16) . . . . ?
C2 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C1 -0.9(2) . . . . ?
C7 C8 C9 C10 179.32(16) . . . . ?
N1 C1 C9 C8 177.06(13) . . . . ?
C2 C1 C9 C8 1.8(2) . . . . ?
N1 C1 C9 C10 -3.2(2) . . . . ?
C2 C1 C9 C10 -178.50(14) . . . . ?
C8 C9 C10 C11 -50.5(2) . . . . ?
C1 C9 C10 C11 129.7(2) . . . . ?
C8 C9 C10 C12 74.4(2) . . . . ?
C1 C9 C10 C12 -105.3(2) . . . . ?
N2 C13 C14 O2 -0.56(16) . . . . ?
N2 C13 C14 C15 175.37(14) . . . . ?
C13 C14 C15 C18 9.9(2) . . . . ?
O2 C14 C15 C18 -174.19(13) . . . . ?
C13 C14 C15 C16 129.29(17) . . . . ?
O2 C14 C15 C16 -54.80(16) . . . . ?
C13 C14 C15 C17 -110.77(19) . . . . ?
O2 C14 C15 C17 65.14(16) . . . . ?
N2 C19 C20 O1 0.77(17) . . . . ?
N2 C19 C20 C21 -176.14(15) . . . . ?
C19 C20 C21 C22 -131.1(2) . . . . ?
O1 C20 C21 C22 52.0(2) . . . . ?
C19 C20 C21 C23 109.6(2) . . . . ?
O1 C20 C21 C23 -67.27(17) . . . . ?
C19 C20 C21 C24 -9.1(3) . . . . ?
O1 C20 C21 C24 174.03(15) . . . . ?
C14 C13 N2 C19 115.04(14) . . . . ?
C14 C13 N2 P1 -4.10(14) . . . . ?
C20 C19 N2 C13 -115.26(14) . . . . ?
C20 C19 N2 P1 4.03(14) . . . . ?
C9 C1 N1 P1 94.35(18) . . . . ?
C2 C1 N1 P1 -90.23(18) . . . . ?
C19 C20 O1 P1 -5.56(14) . . . . ?
C21 C20 O1 P1 171.96(11) . . . . ?
C13 C14 O2 P1 5.34(14) . . . . ?
C15 C14 O2 P1 -171.42(9) . . . . ?
C1 N1 P1 O2 136.51(15) . . . . ?
C1 N1 P1 O1 8.37(18) . . . . ?
C1 N1 P1 N2 -110.80(16) . . . . ?
C14 O2 P1 N1 123.74(9) . . . . ?
C14 O2 P1 O1 -106.64(10) . . . . ?
C14 O2 P1 N2 -6.74(9) . . . . ?
C20 O1 P1 N1 -127.00(10) . . . . ?
C20 O1 P1 O2 106.48(9) . . . . ?
C20 O1 P1 N2 6.90(9) . . . . ?
C13 N2 P1 N1 -112.66(10) . . . . ?
C19 N2 P1 N1 121.03(10) . . . . ?
C13 N2 P1 O2 6.26(9) . . . . ?
C19 N2 P1 O2 -120.06(9) . . . . ?
C13 N2 P1 O1 119.97(9) . . . . ?
C19 N2 P1 O1 -6.34(9) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.058



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

data_8_1821119
_database_code_depnum_ccdc_archive 'CCDC 1821119'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H41 N4 P'
_chemical_formula_weight         416.58

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'
N N 0.0061 0.0033 '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/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                   8.3589(17)
_cell_length_b                   16.491(3)
_cell_length_c                   18.049(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.77(3)
_cell_angle_gamma                90
_cell_volume                     2482.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1831
_cell_measurement_theta_min      2.470
_cell_measurement_theta_max      27.841

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.21
_exptl_transmission_factor_max   0.50
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.209649
_exptl_absorpt_correction_T_max  0.50
_exptl_absorpt_process_details   
'SADABS was used for absorption correction. R(int) was 0.0371 before and 0.0167 after correction. The Ratio of minimum to maximum transmission is 0.2096. The λ/2 correction factor is 0.0015.'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15379
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.674
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_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             4358
_reflns_number_gt                3223
_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       'SMART v5.625 (Bruker, 2001)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0944P)²+1.4980P] 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         4358
_refine_ls_number_parameters     291
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0798
_refine_ls_wR_factor_ref         0.2070
_refine_ls_wR_factor_gt          0.1936
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.085
_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 0.3155(3) 0.60173(19) 0.23011(18) 0.0485(8) Uani 1 1 d . . . . .
C2 C 0.3481(4) 0.6399(2) 0.2999(2) 0.0607(9) Uani 1 1 d . . . . .
C3 C 0.3778(5) 0.7229(3) 0.3014(3) 0.0800(12) Uani 1 1 d . . . . .
H3 H 0.397095 0.748199 0.347185 0.096 Uiso 1 1 calc R U . . .
C4 C 0.3799(5) 0.7688(3) 0.2386(3) 0.0917(14) Uani 1 1 d . . . . .
H4 H 0.397912 0.824428 0.241375 0.110 Uiso 1 1 calc R U . . .
C5 C 0.3550(5) 0.7312(3) 0.1720(3) 0.0837(13) Uani 1 1 d . . . . .
H5 H 0.359394 0.762170 0.129097 0.100 Uiso 1 1 calc R U . . .
C6 C 0.3231(4) 0.6489(2) 0.1647(2) 0.0614(10) Uani 1 1 d . . . . .
C7 C 0.2997(5) 0.6095(3) 0.0893(2) 0.0808(12) Uani 1 1 d . . . . .
H7 H 0.320839 0.551572 0.096829 0.097 Uiso 1 1 calc R U . . .
C8 C 0.4145(7) 0.6385(4) 0.0331(3) 0.127(2) Uani 1 1 d . . . . .
H8A H 0.522755 0.633988 0.054052 0.190 Uiso 1 1 calc R U . . .
H8B H 0.401663 0.605707 -0.010829 0.190 Uiso 1 1 calc R U . . .
H8C H 0.391808 0.694065 0.020586 0.190 Uiso 1 1 calc R U . . .
C9 C 0.1305(7) 0.6163(5) 0.0573(3) 0.145(3) Uani 1 1 d . . . . .
H9A H 0.121109 0.590524 0.009534 0.218 Uiso 1 1 calc R U . . .
H9B H 0.060045 0.590117 0.089820 0.218 Uiso 1 1 calc R U . . .
H9C H 0.101735 0.672421 0.052127 0.218 Uiso 1 1 calc R U . . .
C10 C 0.3586(5) 0.5901(3) 0.3704(2) 0.0710(11) Uani 1 1 d . . . . .
H10 H 0.292000 0.541845 0.360972 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5279(7) 0.5611(4) 0.3876(3) 0.135(2) Uani 1 1 d . . . . .
H11A H 0.565575 0.534476 0.344741 0.202 Uiso 1 1 calc R U . . .
H11B H 0.595728 0.606628 0.400467 0.202 Uiso 1 1 calc R U . . .
H11C H 0.530306 0.523754 0.428418 0.202 Uiso 1 1 calc R U . . .
C12 C 0.2976(10) 0.6319(4) 0.4366(3) 0.167(3) Uani 1 1 d . . . . .
H12A H 0.189708 0.650069 0.425013 0.251 Uiso 1 1 calc R U . . .
H12B H 0.299199 0.594779 0.477658 0.251 Uiso 1 1 calc R U . . .
H12C H 0.364621 0.677652 0.449708 0.251 Uiso 1 1 calc R U . . .
C13 C 0.2704(6) 0.3721(3) 0.3498(3) 0.0968(15) Uani 1 1 d . . . . .
H13A H 0.314198 0.334892 0.314710 0.116 Uiso 0.54(2) 1 calc R U P A 1
H13B H 0.354103 0.409522 0.367111 0.116 Uiso 0.54(2) 1 calc R U P A 1
H13C H 0.371055 0.400118 0.344750 0.116 Uiso 0.46(2) 1 calc R U P A 2
H13D H 0.277569 0.317320 0.330599 0.116 Uiso 0.46(2) 1 calc R U P A 2
C14A C 0.212(3) 0.3277(11) 0.4117(10) 0.126(6) Uani 0.54(2) 1 d . U P A 1
H14A H 0.288579 0.329616 0.454433 0.151 Uiso 0.54(2) 1 calc R U P A 1
H14B H 0.190834 0.271503 0.398550 0.151 Uiso 0.54(2) 1 calc R U P A 1
C14B C 0.220(4) 0.3730(18) 0.4319(11) 0.146(9) Uani 0.46(2) 1 d . U P A 2
H14C H 0.262744 0.326167 0.458901 0.176 Uiso 0.46(2) 1 calc R U P A 2
H14D H 0.258442 0.421740 0.457293 0.176 Uiso 0.46(2) 1 calc R U P A 2
C15 C 0.0598(12) 0.3712(8) 0.4272(5) 0.214(5) Uani 1 1 d . . . . .
H15A H -0.020713 0.332402 0.440499 0.256 Uiso 0.54(2) 1 calc R U P A 1
H15B H 0.079647 0.408425 0.468408 0.256 Uiso 0.54(2) 1 calc R U P A 1
H15C H 0.019015 0.395980 0.470920 0.256 Uiso 0.46(2) 1 calc R U P A 2
H15D H 0.022410 0.315532 0.424168 0.256 Uiso 0.46(2) 1 calc R U P A 2
C16 C 0.0029(7) 0.4158(4) 0.3607(3) 0.131(2) Uani 1 1 d . . . . .
H16A H -0.089232 0.388933 0.336127 0.157 Uiso 1 1 calc R U . . .
H16B H -0.027423 0.470596 0.373333 0.157 Uiso 1 1 calc R U . . .
C17 C -0.1672(6) 0.4601(3) 0.1782(4) 0.1089(18) Uani 1 1 d . . . . .
H17A H -0.207571 0.419127 0.210800 0.131 Uiso 0.54(2) 1 calc R U P A 1
H17B H -0.137629 0.433996 0.132954 0.131 Uiso 0.54(2) 1 calc R U P A 1
H17C H -0.151578 0.452141 0.125964 0.131 Uiso 0.46(2) 1 calc R U P A 2
H17D H -0.182000 0.407500 0.200920 0.131 Uiso 0.46(2) 1 calc R U P A 2
C18A C -0.295(3) 0.526(2) 0.1607(17) 0.118(9) Uani 0.54(2) 1 d . U P A 1
H18A H -0.309453 0.534759 0.107552 0.142 Uiso 0.54(2) 1 calc R U P A 1
H18B H -0.396998 0.509612 0.178822 0.142 Uiso 0.54(2) 1 calc R U P A 1
C18B C -0.300(3) 0.509(3) 0.187(2) 0.128(12) Uani 0.46(2) 1 d . U P A 2
H18C H -0.355206 0.492396 0.230051 0.153 Uiso 0.46(2) 1 calc R U P A 2
H18D H -0.374344 0.505962 0.143525 0.153 Uiso 0.46(2) 1 calc R U P A 2
C19 C -0.2365(5) 0.5970(3) 0.1975(4) 0.1162(19) Uani 1 1 d . . . . .
H19A H -0.313132 0.615135 0.232014 0.139 Uiso 0.54(2) 1 calc R U P A 1
H19B H -0.224293 0.639679 0.161347 0.139 Uiso 0.54(2) 1 calc R U P A 1
H19C H -0.223507 0.623389 0.150242 0.139 Uiso 0.46(2) 1 calc R U P A 2
H19D H -0.305978 0.629476 0.226594 0.139 Uiso 0.46(2) 1 calc R U P A 2
C20 C -0.0797(5) 0.5809(3) 0.2383(3) 0.0884(14) Uani 1 1 d . . . . .
H20A H -0.001516 0.621498 0.226367 0.106 Uiso 1 1 calc R U . . .
H20B H -0.090594 0.581475 0.291485 0.106 Uiso 1 1 calc R U . . .
C21 C 0.2422(5) 0.3888(3) 0.1071(2) 0.0772(12) Uani 1 1 d . . . . .
H21A H 0.353290 0.405578 0.114740 0.093 Uiso 1 1 calc R U . . .
H21B H 0.186057 0.427147 0.073878 0.093 Uiso 1 1 calc R U . . .
C22 C 0.2307(7) 0.3041(3) 0.0755(3) 0.0958(15) Uani 1 1 d . . . . .
H22A H 0.327594 0.273345 0.088182 0.115 Uiso 0.54(2) 1 calc R U P A 1
H22B H 0.210687 0.304983 0.022003 0.115 Uiso 0.54(2) 1 calc R U P A 1
H22C H 0.154580 0.302572 0.032609 0.115 Uiso 0.46(2) 1 calc R U P A 2
H22D H 0.334328 0.286494 0.060389 0.115 Uiso 0.46(2) 1 calc R U P A 2
C23A C 0.088(2) 0.2692(7) 0.1134(7) 0.090(4) Uani 0.54(2) 1 d . U P A 1
H23A H -0.012019 0.285152 0.087116 0.107 Uiso 0.54(2) 1 calc R U P A 1
H23B H 0.093403 0.210433 0.114877 0.107 Uiso 0.54(2) 1 calc R U P A 1
C23B C 0.177(3) 0.2506(9) 0.1347(12) 0.100(5) Uani 0.46(2) 1 d . U P A 2
H23C H 0.101343 0.210568 0.113969 0.119 Uiso 0.46(2) 1 calc R U P A 2
H23D H 0.267276 0.222485 0.159249 0.119 Uiso 0.46(2) 1 calc R U P A 2
C24 C 0.0997(7) 0.3024(2) 0.1874(3) 0.0995(16) Uani 1 1 d . . . . .
H24A H 0.170077 0.269830 0.220257 0.119 Uiso 0.54(2) 1 calc R U P A 1
H24B H -0.004977 0.305423 0.207456 0.119 Uiso 0.54(2) 1 calc R U P A 1
H24C H 0.123137 0.283461 0.237796 0.119 Uiso 0.46(2) 1 calc R U P A 2
H24D H -0.015653 0.302750 0.176914 0.119 Uiso 0.46(2) 1 calc R U P A 2
N1 N 0.2873(3) 0.51866(15) 0.22489(14) 0.0482(7) Uani 1 1 d . . . . .
N2 N 0.1334(4) 0.41679(19) 0.31396(16) 0.0667(9) Uani 1 1 d . . . . .
N3 N -0.0308(3) 0.50116(17) 0.21426(17) 0.0603(8) Uani 1 1 d . . . . .
N4 N 0.1671(4) 0.38420(16) 0.17739(16) 0.0619(8) Uani 1 1 d . . . . .
P1 P 0.14673(10) 0.46104(5) 0.23296(5) 0.0461(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.392(4) . ?
C1 C6 1.418(5) . ?
C1 C2 1.418(5) . ?
C2 C3 1.391(5) . ?
C2 C10 1.513(5) . ?
C3 C4 1.364(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(6) . ?
C7 C9 1.496(7) . ?
C7 C8 1.519(6) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12 1.498(6) . ?
C10 C11 1.506(7) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14A 1.447(16) . ?
C13 N2 1.475(5) . ?
C13 C14B 1.57(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C13 H13D 0.9700 . ?
C14A C15 1.50(2) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C14B C15 1.33(3) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15 C16 1.461(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C16 N2 1.422(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18B 1.39(3) . ?
C17 N3 1.444(5) . ?
C17 C18A 1.54(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C17 H17D 0.9700 . ?
C18A C19 1.42(3) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18B C19 1.55(4) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19 C20 1.485(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C19 H19D 0.9700 . ?
C20 N3 1.452(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 N4 1.455(4) . ?
C21 C22 1.510(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23B 1.479(18) . ?
C22 C23A 1.525(16) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C22 H22D 0.9700 . ?
C23A C24 1.441(12) . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C23B C24 1.458(14) . ?
C23B H23C 0.9700 . ?
C23B H23D 0.9700 . ?
C24 N4 1.478(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C24 H24D 0.9700 . ?
N1 P1 1.525(3) . ?
N2 P1 1.644(3) . ?
N3 P1 1.639(3) . ?
N4 P1 1.632(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
N1 C1 C6 120.0(3) . . ?
N1 C1 C2 121.3(3) . . ?
C6 C1 C2 118.6(3) . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 C10 121.1(4) . . ?
C1 C2 C10 120.2(3) . . ?
C4 C3 C2 122.8(4) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 123.2(4) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C5 C6 C1 118.4(4) . . ?
C5 C6 C7 121.2(4) . . ?
C1 C6 C7 120.3(3) . . ?
C9 C7 C6 112.3(4) . . ?
C9 C7 C8 110.0(4) . . ?
C6 C7 C8 114.7(4) . . ?
C9 C7 H7 106.4 . . ?
C6 C7 H7 106.4 . . ?
C8 C7 H7 106.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C10 C11 110.3(5) . . ?
C12 C10 C2 114.7(4) . . ?
C11 C10 C2 110.3(3) . . ?
C12 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C2 C10 H10 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14A C13 N2 107.4(10) . . ?
N2 C13 C14B 99.1(12) . . ?
C14A C13 H13A 110.2 . . ?
N2 C13 H13A 110.2 . . ?
C14A C13 H13B 110.2 . . ?
N2 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
N2 C13 H13C 111.9 . . ?
C14B C13 H13C 111.9 . . ?
N2 C13 H13D 111.9 . . ?
C14B C13 H13D 111.9 . . ?
H13C C13 H13D 109.6 . . ?
C13 C14A C15 103.6(10) . . ?
C13 C14A H14A 111.0 . . ?
C15 C14A H14A 111.0 . . ?
C13 C14A H14B 111.0 . . ?
C15 C14A H14B 111.0 . . ?
H14A C14A H14B 109.0 . . ?
C15 C14B C13 105.8(14) . . ?
C15 C14B H14C 110.6 . . ?
C13 C14B H14C 110.6 . . ?
C15 C14B H14D 110.6 . . ?
C13 C14B H14D 110.6 . . ?
H14C C14B H14D 108.7 . . ?
C14B C15 C16 108.2(10) . . ?
C16 C15 C14A 108.7(8) . . ?
C16 C15 H15A 109.9 . . ?
C14A C15 H15A 109.9 . . ?
C16 C15 H15B 109.9 . . ?
C14A C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C14B C15 H15C 110.1 . . ?
C16 C15 H15C 110.1 . . ?
C14B C15 H15D 110.1 . . ?
C16 C15 H15D 110.1 . . ?
H15C C15 H15D 108.4 . . ?
N2 C16 C15 105.8(5) . . ?
N2 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
N2 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C18B C17 N3 106.7(15) . . ?
N3 C17 C18A 106.3(11) . . ?
N3 C17 H17A 110.5 . . ?
C18A C17 H17A 110.5 . . ?
N3 C17 H17B 110.5 . . ?
C18A C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
C18B C17 H17C 110.4 . . ?
N3 C17 H17C 110.4 . . ?
C18B C17 H17D 110.4 . . ?
N3 C17 H17D 110.4 . . ?
H17C C17 H17D 108.6 . . ?
C19 C18A C17 105.8(17) . . ?
C19 C18A H18A 110.6 . . ?
C17 C18A H18A 110.6 . . ?
C19 C18A H18B 110.6 . . ?
C17 C18A H18B 110.6 . . ?
H18A C18A H18B 108.7 . . ?
C17 C18B C19 106.8(19) . . ?
C17 C18B H18C 110.4 . . ?
C19 C18B H18C 110.4 . . ?
C17 C18B H18D 110.4 . . ?
C19 C18B H18D 110.4 . . ?
H18C C18B H18D 108.6 . . ?
C18A C19 C20 110.5(12) . . ?
C20 C19 C18B 100.3(12) . . ?
C18A C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
C18A C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19C 111.7 . . ?
C18B C19 H19C 111.7 . . ?
C20 C19 H19D 111.7 . . ?
C18B C19 H19D 111.7 . . ?
H19C C19 H19D 109.5 . . ?
N3 C20 C19 105.7(4) . . ?
N3 C20 H20A 110.6 . . ?
C19 C20 H20A 110.6 . . ?
N3 C20 H20B 110.6 . . ?
C19 C20 H20B 110.6 . . ?
H20A C20 H20B 108.7 . . ?
N4 C21 C22 105.0(3) . . ?
N4 C21 H21A 110.7 . . ?
C22 C21 H21A 110.7 . . ?
N4 C21 H21B 110.7 . . ?
C22 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
C23B C22 C21 107.2(6) . . ?
C21 C22 C23A 102.3(6) . . ?
C21 C22 H22A 111.3 . . ?
C23A C22 H22A 111.3 . . ?
C21 C22 H22B 111.3 . . ?
C23A C22 H22B 111.3 . . ?
H22A C22 H22B 109.2 . . ?
C23B C22 H22C 110.3 . . ?
C21 C22 H22C 110.3 . . ?
C23B C22 H22D 110.3 . . ?
C21 C22 H22D 110.3 . . ?
H22C C22 H22D 108.5 . . ?
C24 C23A C22 105.3(8) . . ?
C24 C23A H23A 110.7 . . ?
C22 C23A H23A 110.7 . . ?
C24 C23A H23B 110.7 . . ?
C22 C23A H23B 110.7 . . ?
H23A C23A H23B 108.8 . . ?
C24 C23B C22 106.9(10) . . ?
C24 C23B H23C 110.3 . . ?
C22 C23B H23C 110.3 . . ?
C24 C23B H23D 110.3 . . ?
C22 C23B H23D 110.3 . . ?
H23C C23B H23D 108.6 . . ?
C23A C24 N4 103.7(6) . . ?
C23B C24 N4 105.5(7) . . ?
C23A C24 H24A 111.0 . . ?
N4 C24 H24A 111.0 . . ?
C23A C24 H24B 111.0 . . ?
N4 C24 H24B 111.0 . . ?
H24A C24 H24B 109.0 . . ?
C23B C24 H24C 110.6 . . ?
N4 C24 H24C 110.6 . . ?
C23B C24 H24D 110.6 . . ?
N4 C24 H24D 110.6 . . ?
H24C C24 H24D 108.8 . . ?
C1 N1 P1 137.3(2) . . ?
C16 N2 C13 109.8(4) . . ?
C16 N2 P1 129.2(3) . . ?
C13 N2 P1 121.0(3) . . ?
C17 N3 C20 109.3(3) . . ?
C17 N3 P1 125.5(3) . . ?
C20 N3 P1 125.0(3) . . ?
C21 N4 C24 110.1(3) . . ?
C21 N4 P1 124.3(2) . . ?
C24 N4 P1 125.3(3) . . ?
N1 P1 N4 108.23(14) . . ?
N1 P1 N3 114.91(15) . . ?
N4 P1 N3 108.45(16) . . ?
N1 P1 N2 117.32(15) . . ?
N4 P1 N2 102.58(15) . . ?
N3 P1 N2 104.41(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
N1 C1 C2 C3 179.0(3) . . . . ?
C6 C1 C2 C3 3.4(5) . . . . ?
N1 C1 C2 C10 2.2(5) . . . . ?
C6 C1 C2 C10 -173.5(3) . . . . ?
C1 C2 C3 C4 -1.3(6) . . . . ?
C10 C2 C3 C4 175.6(4) . . . . ?
C2 C3 C4 C5 -1.3(7) . . . . ?
C3 C4 C5 C6 1.8(7) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
C4 C5 C6 C7 -178.7(4) . . . . ?
N1 C1 C6 C5 -178.6(3) . . . . ?
C2 C1 C6 C5 -2.9(5) . . . . ?
N1 C1 C6 C7 0.4(5) . . . . ?
C2 C1 C6 C7 176.1(3) . . . . ?
C5 C6 C7 C9 -85.5(5) . . . . ?
C1 C6 C7 C9 95.5(5) . . . . ?
C5 C6 C7 C8 41.1(6) . . . . ?
C1 C6 C7 C8 -137.9(4) . . . . ?
C3 C2 C10 C12 37.8(6) . . . . ?
C1 C2 C10 C12 -145.5(5) . . . . ?
C3 C2 C10 C11 -87.5(5) . . . . ?
C1 C2 C10 C11 89.3(5) . . . . ?
N2 C13 C14A C15 -20.3(18) . . . . ?
N2 C13 C14B C15 32(2) . . . . ?
C13 C14B C15 C16 -33(2) . . . . ?
C13 C14A C15 C16 21(2) . . . . ?
C14B C15 C16 N2 21(2) . . . . ?
C14A C15 C16 N2 -14.0(16) . . . . ?
N3 C17 C18A C19 -9(2) . . . . ?
N3 C17 C18B C19 25(3) . . . . ?
C17 C18A C19 C20 -1(2) . . . . ?
C17 C18B C19 C20 -34(3) . . . . ?
C18A C19 C20 N3 10.0(16) . . . . ?
C18B C19 C20 N3 28.9(16) . . . . ?
N4 C21 C22 C23B -10.2(12) . . . . ?
N4 C21 C22 C23A 24.2(7) . . . . ?
C21 C22 C23A C24 -36.6(11) . . . . ?
C21 C22 C23B C24 21.0(18) . . . . ?
C22 C23A C24 N4 33.9(11) . . . . ?
C22 C23B C24 N4 -23.3(18) . . . . ?
C6 C1 N1 P1 -102.9(4) . . . . ?
C2 C1 N1 P1 81.5(4) . . . . ?
C15 C16 N2 C13 1.1(8) . . . . ?
C15 C16 N2 P1 -177.1(6) . . . . ?
C14A C13 N2 C16 12.7(11) . . . . ?
C14B C13 N2 C16 -18.8(11) . . . . ?
C14A C13 N2 P1 -169.0(10) . . . . ?
C14B C13 N2 P1 159.5(11) . . . . ?
C18B C17 N3 C20 -6(2) . . . . ?
C18A C17 N3 C20 15.6(14) . . . . ?
C18B C17 N3 P1 167.9(19) . . . . ?
C18A C17 N3 P1 -170.3(13) . . . . ?
C19 C20 N3 C17 -15.9(5) . . . . ?
C19 C20 N3 P1 170.0(3) . . . . ?
C22 C21 N4 C24 -4.3(5) . . . . ?
C22 C21 N4 P1 -179.1(3) . . . . ?
C23A C24 N4 C21 -18.7(9) . . . . ?
C23B C24 N4 C21 17.3(13) . . . . ?
C23A C24 N4 P1 156.0(8) . . . . ?
C23B C24 N4 P1 -168.0(12) . . . . ?
C1 N1 P1 N4 148.9(3) . . . . ?
C1 N1 P1 N3 27.5(4) . . . . ?
C1 N1 P1 N2 -95.8(4) . . . . ?
C21 N4 P1 N1 -31.1(4) . . . . ?
C24 N4 P1 N1 154.9(4) . . . . ?
C21 N4 P1 N3 94.2(3) . . . . ?
C24 N4 P1 N3 -79.8(4) . . . . ?
C21 N4 P1 N2 -155.7(3) . . . . ?
C24 N4 P1 N2 30.2(4) . . . . ?
C17 N3 P1 N1 143.7(4) . . . . ?
C20 N3 P1 N1 -43.1(4) . . . . ?
C17 N3 P1 N4 22.5(4) . . . . ?
C20 N3 P1 N4 -164.3(3) . . . . ?
C17 N3 P1 N2 -86.3(4) . . . . ?
C20 N3 P1 N2 86.9(4) . . . . ?
C16 N2 P1 N1 125.5(5) . . . . ?
C13 N2 P1 N1 -52.5(4) . . . . ?
C16 N2 P1 N4 -116.1(5) . . . . ?
C13 N2 P1 N4 66.0(4) . . . . ?
C16 N2 P1 N3 -3.0(5) . . . . ?
C13 N2 P1 N3 179.0(3) . . . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_7_1821118
_database_code_depnum_ccdc_archive 'CCDC 1821118'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H33 N2 O2 P'
_chemical_formula_weight         436.51

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'
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                   8.587(2)
_cell_length_b                   17.687(5)
_cell_length_c                   16.430(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.539(6)
_cell_angle_gamma                90
_cell_volume                     2460.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    4676
_cell_measurement_theta_min      2.305
_cell_measurement_theta_max      28.275

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.243577
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   
'SADABS was used for absorption correction. R(int) was 0.0676 before and 0.0089 after correction. The Ratio of minimum to maximum transmission is 0.2436. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_special_details           
'The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.'

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11025
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.704
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4251
_reflns_number_gt                3628
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0744P)²+1.1894P] 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         4251
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.5173(2) 0.28509(11) 0.61986(11) 0.0328(4) Uani 1 1 d . . . . .
C2 C 0.5929(2) 0.35582(11) 0.62136(12) 0.0389(5) Uani 1 1 d . . . . .
C3 C 0.6863(3) 0.37116(14) 0.56196(15) 0.0530(6) Uani 1 1 d . . . . .
H3 H 0.736205 0.418466 0.561920 0.064 Uiso 1 1 calc R U . . .
C4 C 0.7072(3) 0.31837(14) 0.50313(15) 0.0565(6) Uani 1 1 d . . . . .
H4 H 0.769869 0.329879 0.462986 0.068 Uiso 1 1 calc R U . . .
C5 C 0.6364(3) 0.24911(14) 0.50333(13) 0.0489(6) Uani 1 1 d . . . . .
H5 H 0.652809 0.213224 0.463402 0.059 Uiso 1 1 calc R U . . .
C6 C 0.5408(2) 0.23014(11) 0.56087(12) 0.0382(5) Uani 1 1 d . . . . .
C7 C 0.4701(3) 0.15184(12) 0.55814(14) 0.0487(6) Uani 1 1 d . . . . .
H7 H 0.392416 0.151182 0.596429 0.058 Uiso 1 1 calc R U . . .
C8 C 0.3831(4) 0.13054(18) 0.47306(19) 0.0788(9) Uani 1 1 d . . . . .
H8A H 0.457974 0.126560 0.435049 0.118 Uiso 1 1 calc R U . . .
H8B H 0.305460 0.169109 0.453734 0.118 Uiso 1 1 calc R U . . .
H8C H 0.330454 0.082352 0.476061 0.118 Uiso 1 1 calc R U . . .
C9 C 0.5964(4) 0.09298(14) 0.5885(2) 0.0756(8) Uani 1 1 d . . . . .
H9A H 0.548442 0.043234 0.586693 0.113 Uiso 1 1 calc R U . . .
H9B H 0.644465 0.104647 0.644754 0.113 Uiso 1 1 calc R U . . .
H9C H 0.676664 0.093670 0.553312 0.113 Uiso 1 1 calc R U . . .
C10 C 0.5688(3) 0.41479(12) 0.68454(14) 0.0485(6) Uani 1 1 d . . . . .
H10 H 0.521777 0.388388 0.727728 0.058 Uiso 1 1 calc R U . . .
C11 C 0.7195(4) 0.4515(2) 0.7276(2) 0.0949(11) Uani 1 1 d . . . . .
H11A H 0.769698 0.478311 0.687486 0.142 Uiso 1 1 calc R U . . .
H11B H 0.790512 0.412818 0.754165 0.142 Uiso 1 1 calc R U . . .
H11C H 0.694778 0.486734 0.768867 0.142 Uiso 1 1 calc R U . . .
C12 C 0.4518(5) 0.4743(2) 0.6486(2) 0.0998(12) Uani 1 1 d . . . . .
H12A H 0.492951 0.501577 0.605532 0.150 Uiso 1 1 calc R U . . .
H12B H 0.434391 0.509301 0.691642 0.150 Uiso 1 1 calc R U . . .
H12C H 0.352710 0.450346 0.625453 0.150 Uiso 1 1 calc R U . . .
C13 C 0.5070(3) 0.13658(11) 0.82065(13) 0.0404(5) Uani 1 1 d . . . . .
C14 C 0.6466(3) 0.17471(14) 0.81846(16) 0.0574(6) Uani 1 1 d . . . . .
H14 H 0.657008 0.206596 0.773899 0.069 Uiso 1 1 calc R U . . .
C15 C 0.7693(3) 0.16533(17) 0.88205(19) 0.0724(8) Uani 1 1 d . . . . .
H15 H 0.865070 0.190776 0.881018 0.087 Uiso 1 1 calc R U . . .
C16 C 0.7545(4) 0.1196(2) 0.94691(18) 0.0790(9) Uani 1 1 d . . . . .
H16 H 0.839178 0.114221 0.990788 0.095 Uiso 1 1 calc R U . . .
C17 C 0.6152(4) 0.08093(18) 0.94834(16) 0.0746(9) Uani 1 1 d . . . . .
H17 H 0.605700 0.048929 0.992931 0.090 Uiso 1 1 calc R U . . .
C18 C 0.4892(3) 0.08920(13) 0.88415(14) 0.0523(6) Uani 1 1 d . . . . .
H18 H 0.394141 0.062901 0.884352 0.063 Uiso 1 1 calc R U . . .
C19 C 0.3005(3) 0.33864(12) 0.82531(12) 0.0428(5) Uani 1 1 d . . . . .
C20 C 0.4234(3) 0.36798(16) 0.87863(14) 0.0619(7) Uani 1 1 d . . . . .
H20 H 0.507116 0.336808 0.902721 0.074 Uiso 1 1 calc R U . . .
C21 C 0.4237(4) 0.44441(19) 0.89707(18) 0.0797(9) Uani 1 1 d . . . . .
H21 H 0.508573 0.465362 0.933622 0.096 Uiso 1 1 calc R U . . .
C22 C 0.3006(4) 0.48974(17) 0.8621(2) 0.0803(9) Uani 1 1 d . . . . .
H22 H 0.300783 0.541538 0.874949 0.096 Uiso 1 1 calc R U . . .
C23 C 0.1795(4) 0.45961(16) 0.8094(2) 0.0728(8) Uani 1 1 d . . . . .
H23 H 0.095820 0.490807 0.785363 0.087 Uiso 1 1 calc R U . . .
C24 C 0.1768(3) 0.38381(14) 0.79039(16) 0.0565(6) Uani 1 1 d . . . . .
H24 H 0.091402 0.363132 0.753969 0.068 Uiso 1 1 calc R U . . .
C25 C 0.0846(4) 0.2367(2) 0.59369(19) 0.0860(10) Uani 1 1 d . . . . .
H25A H 0.029008 0.197067 0.559811 0.129 Uiso 1 1 calc R U . . .
H25B H 0.172261 0.254550 0.568485 0.129 Uiso 1 1 calc R U . . .
H25C H 0.012892 0.278274 0.598213 0.129 Uiso 1 1 calc R U . . .
C26 C 0.0242(3) 0.1744(2) 0.7181(2) 0.0908(11) Uani 1 1 d . . . . .
H26A H -0.058007 0.211356 0.721261 0.136 Uiso 1 1 calc R U . . .
H26B H 0.072893 0.159845 0.773438 0.136 Uiso 1 1 calc R U . . .
H26C H -0.021470 0.130143 0.688410 0.136 Uiso 1 1 calc R U . . .
N1 N 0.4195(2) 0.27302(9) 0.67805(11) 0.0465(5) Uani 1 1 d . . . . .
N2 N 0.1436(2) 0.20724(12) 0.67480(13) 0.0583(6) Uani 1 1 d . . . . .
O1 O 0.37864(16) 0.14416(8) 0.75689(9) 0.0405(3) Uani 1 1 d . . . . .
O2 O 0.29964(19) 0.26148(8) 0.81011(9) 0.0481(4) Uani 1 1 d . . . . .
P1 P 0.31882(6) 0.22595(3) 0.72287(3) 0.03564(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 N1 1.390(2) . ?
C1 C2 1.408(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.389(3) . ?
C2 C10 1.510(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.510(3) . ?
C7 C8 1.519(4) . ?
C7 C9 1.526(4) . ?
C7 H7 0.9900 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C12 1.507(4) . ?
C10 C11 1.514(4) . ?
C10 H10 0.9900 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 C18 1.366(3) . ?
C13 C14 1.381(3) . ?
C13 O1 1.396(3) . ?
C14 C15 1.365(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.361(5) . ?
C15 H15 0.9400 . ?
C16 C17 1.381(5) . ?
C16 H16 0.9400 . ?
C17 C18 1.388(4) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.358(3) . ?
C19 C24 1.376(3) . ?
C19 O2 1.387(3) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9400 . ?
C21 C22 1.375(4) . ?
C21 H21 0.9400 . ?
C22 C23 1.347(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.376(4) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 N2 1.442(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C26 N2 1.462(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
N1 P1 1.4810(17) . ?
N2 P1 1.613(2) . ?
O1 P1 1.6044(15) . ?
O2 P1 1.5985(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 116.99(17) . . ?
N1 C1 C6 122.58(17) . . ?
C2 C1 C6 120.43(17) . . ?
C3 C2 C1 118.66(19) . . ?
C3 C2 C10 120.59(19) . . ?
C1 C2 C10 120.72(17) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 122.0(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 117.91(19) . . ?
C5 C6 C7 118.70(19) . . ?
C1 C6 C7 123.37(17) . . ?
C6 C7 C8 112.9(2) . . ?
C6 C7 C9 110.8(2) . . ?
C8 C7 C9 110.2(2) . . ?
C6 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C9 C7 H7 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C10 C2 111.8(2) . . ?
C12 C10 C11 110.3(3) . . ?
C2 C10 C11 114.5(2) . . ?
C12 C10 H10 106.6 . . ?
C2 C10 H10 106.6 . . ?
C11 C10 H10 106.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 121.8(2) . . ?
C18 C13 O1 117.2(2) . . ?
C14 C13 O1 121.0(2) . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 118.2(3) . . ?
C13 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C20 C19 C24 120.7(2) . . ?
C20 C19 O2 118.2(2) . . ?
C24 C19 O2 121.0(2) . . ?
C19 C20 C21 119.2(3) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.9(3) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C19 C24 C23 119.2(3) . . ?
C19 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 N1 P1 153.82(15) . . ?
C25 N2 C26 115.2(2) . . ?
C25 N2 P1 122.31(19) . . ?
C26 N2 P1 121.0(2) . . ?
C13 O1 P1 121.03(12) . . ?
C19 O2 P1 123.36(12) . . ?
N1 P1 O2 112.35(9) . . ?
N1 P1 O1 120.04(9) . . ?
O2 P1 O1 96.70(8) . . ?
N1 P1 N2 116.46(11) . . ?
O2 P1 N2 107.06(11) . . ?
O1 P1 N2 101.79(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
N1 C1 C2 C3 -177.3(2) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
N1 C1 C2 C10 0.8(3) . . . . ?
C6 C1 C2 C10 -179.76(19) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C10 C2 C3 C4 -178.9(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -178.6(2) . . . . ?
N1 C1 C6 C5 177.5(2) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
N1 C1 C6 C7 -3.6(3) . . . . ?
C2 C1 C6 C7 176.92(19) . . . . ?
C5 C6 C7 C8 -52.1(3) . . . . ?
C1 C6 C7 C8 129.1(2) . . . . ?
C5 C6 C7 C9 72.1(3) . . . . ?
C1 C6 C7 C9 -106.7(2) . . . . ?
C3 C2 C10 C12 77.3(3) . . . . ?
C1 C2 C10 C12 -100.7(3) . . . . ?
C3 C2 C10 C11 -49.0(3) . . . . ?
C1 C2 C10 C11 132.9(2) . . . . ?
C18 C13 C14 C15 -0.8(4) . . . . ?
O1 C13 C14 C15 -179.7(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C17 1.1(5) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C14 C13 C18 C17 1.2(3) . . . . ?
O1 C13 C18 C17 -179.9(2) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
C24 C19 C20 C21 -0.6(4) . . . . ?
O2 C19 C20 C21 -177.6(2) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C20 C21 C22 C23 -0.3(5) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C20 C19 C24 C23 0.7(4) . . . . ?
O2 C19 C24 C23 177.6(2) . . . . ?
C22 C23 C24 C19 -0.6(4) . . . . ?
C2 C1 N1 P1 -171.7(3) . . . . ?
C6 C1 N1 P1 8.9(5) . . . . ?
C18 C13 O1 P1 132.35(17) . . . . ?
C14 C13 O1 P1 -48.7(2) . . . . ?
C20 C19 O2 P1 -112.7(2) . . . . ?
C24 C19 O2 P1 70.2(2) . . . . ?
C1 N1 P1 O2 158.3(4) . . . . ?
C1 N1 P1 O1 45.8(4) . . . . ?
C1 N1 P1 N2 -77.7(4) . . . . ?
C19 O2 P1 N1 31.5(2) . . . . ?
C19 O2 P1 O1 157.88(17) . . . . ?
C19 O2 P1 N2 -97.57(18) . . . . ?
C13 O1 P1 N1 67.47(18) . . . . ?
C13 O1 P1 O2 -53.20(15) . . . . ?
C13 O1 P1 N2 -162.24(15) . . . . ?
C25 N2 P1 N1 -2.2(3) . . . . ?
C26 N2 P1 N1 -167.9(2) . . . . ?
C25 N2 P1 O2 124.5(2) . . . . ?
C26 N2 P1 O2 -41.2(3) . . . . ?
C25 N2 P1 O1 -134.7(2) . . . . ?
C26 N2 P1 O1 59.7(2) . . . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_4_1821117
_database_code_depnum_ccdc_archive 'CCDC 1821117'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H31 N4 P'
_chemical_formula_weight         430.52

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'
N N 0.0061 0.0033 '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                   12.8565(18)
_cell_length_b                   9.4531(13)
_cell_length_c                   19.152(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.382(4)
_cell_angle_gamma                90
_cell_volume                     2313.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7653
_cell_measurement_theta_min      2.400
_cell_measurement_theta_max      28.201

_exptl_crystal_description       cubical
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15190
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5662
_reflns_number_gt                4937
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0756P)²+0.5252P] 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         5662
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.64669(9) 0.81575(13) 0.12546(6) 0.0273(2) Uani 1 1 d . . . . .
C2 C 0.56093(10) 0.90245(14) 0.13865(7) 0.0316(3) Uani 1 1 d . . . . .
C3 C 0.45961(10) 0.85326(16) 0.12181(8) 0.0376(3) Uani 1 1 d . . . . .
H3 H 0.402995 0.910535 0.131122 0.045 Uiso 1 1 calc R U . . .
C4 C 0.44019(11) 0.72197(17) 0.09166(8) 0.0412(3) Uani 1 1 d . . . . .
H4 H 0.371167 0.689253 0.081242 0.049 Uiso 1 1 calc R U . . .
C5 C 0.52357(11) 0.63942(16) 0.07703(8) 0.0392(3) Uani 1 1 d . . . . .
H5 H 0.510197 0.550782 0.055648 0.047 Uiso 1 1 calc R U . . .
C6 C 0.62725(10) 0.68336(14) 0.09297(7) 0.0320(3) Uani 1 1 d . . . . .
C7 C 0.71419(11) 0.58817(15) 0.07277(9) 0.0431(4) Uani 1 1 d . . . . .
H7 H 0.781291 0.623832 0.096706 0.052 Uiso 1 1 calc R U . . .
C8 C 0.70218(14) 0.43435(18) 0.09435(12) 0.0583(5) Uani 1 1 d . . . . .
H8A H 0.700992 0.428987 0.144829 0.087 Uiso 1 1 calc R U . . .
H8B H 0.760616 0.379546 0.080994 0.087 Uiso 1 1 calc R U . . .
H8C H 0.637293 0.396621 0.070942 0.087 Uiso 1 1 calc R U . . .
C9 C 0.71945(14) 0.5971(2) -0.00686(11) 0.0587(5) Uani 1 1 d . . . . .
H9A H 0.656105 0.557341 -0.031441 0.088 Uiso 1 1 calc R U . . .
H9B H 0.779606 0.544278 -0.018963 0.088 Uiso 1 1 calc R U . . .
H9C H 0.725973 0.695264 -0.020439 0.088 Uiso 1 1 calc R U . . .
C10 C 0.57957(12) 1.04582(16) 0.17292(9) 0.0427(3) Uani 1 1 d . . . . .
H10 H 0.648545 1.079533 0.161402 0.051 Uiso 1 1 calc R U . . .
C11 C 0.49892(16) 1.15732(19) 0.14605(13) 0.0662(5) Uani 1 1 d . . . . .
H11A H 0.492112 1.159153 0.095107 0.099 Uiso 1 1 calc R U . . .
H11B H 0.521598 1.249433 0.164149 0.099 Uiso 1 1 calc R U . . .
H11C H 0.431840 1.134188 0.161827 0.099 Uiso 1 1 calc R U . . .
C12 C 0.58701(19) 1.0311(2) 0.25229(10) 0.0708(6) Uani 1 1 d . . . . .
H12A H 0.519520 1.002875 0.265790 0.106 Uiso 1 1 calc R U . . .
H12B H 0.607323 1.121123 0.274023 0.106 Uiso 1 1 calc R U . . .
H12C H 0.638921 0.960040 0.267742 0.106 Uiso 1 1 calc R U . . .
C13 C 0.74882(13) 1.04745(17) 0.01018(9) 0.0461(4) Uani 1 1 d . . . . .
H13A H 0.774622 1.117066 -0.020879 0.069 Uiso 1 1 calc R U . . .
H13B H 0.718980 1.095308 0.048094 0.069 Uiso 1 1 calc R U . . .
H13C H 0.695510 0.989910 -0.016018 0.069 Uiso 1 1 calc R U . . .
C14 C 0.89006(10) 0.87411(13) -0.00478(7) 0.0303(3) Uani 1 1 d . . . . .
C15 C 0.87868(12) 0.87247(16) -0.07733(7) 0.0385(3) Uani 1 1 d . . . . .
H15 H 0.833508 0.936416 -0.103163 0.046 Uiso 1 1 calc R U . . .
C16 C 0.93578(13) 0.77375(17) -0.11122(8) 0.0439(3) Uani 1 1 d . . . . .
H16 H 0.928146 0.770560 -0.160581 0.053 Uiso 1 1 calc R U . . .
C17 C 1.00322(13) 0.68064(17) -0.07401(8) 0.0447(4) Uani 1 1 d . . . . .
H17 H 1.041897 0.616139 -0.098142 0.054 Uiso 1 1 calc R U . . .
C18 C 1.01447(11) 0.68150(15) -0.00072(8) 0.0373(3) Uani 1 1 d . . . . .
H18 H 1.059953 0.617627 0.024913 0.045 Uiso 1 1 calc R U . . .
C19 C 0.95754(10) 0.77790(13) 0.03327(6) 0.0282(2) Uani 1 1 d . . . . .
C20 C 1.03983(10) 0.81545(13) 0.15634(7) 0.0297(3) Uani 1 1 d . . . . .
C21 C 1.13368(11) 0.74344(16) 0.16429(8) 0.0411(3) Uani 1 1 d . . . . .
H21 H 1.145673 0.667266 0.134664 0.049 Uiso 1 1 calc R U . . .
C22 C 1.21042(12) 0.78631(19) 0.21733(10) 0.0529(4) Uani 1 1 d . . . . .
H22 H 1.275464 0.739858 0.222939 0.063 Uiso 1 1 calc R U . . .
C23 C 1.19176(13) 0.89588(19) 0.26147(10) 0.0522(4) Uani 1 1 d . . . . .
H23 H 1.244096 0.922396 0.297289 0.063 Uiso 1 1 calc R U . . .
C24 C 1.09691(12) 0.96834(16) 0.25418(8) 0.0412(3) Uani 1 1 d . . . . .
H24 H 1.084399 1.042348 0.284941 0.049 Uiso 1 1 calc R U . . .
C25 C 1.02163(10) 0.92879(14) 0.20061(7) 0.0309(3) Uani 1 1 d . . . . .
C26 C 0.88227(13) 1.09810(17) 0.22689(9) 0.0461(4) Uani 1 1 d . . . . .
H26A H 0.876933 1.060811 0.273546 0.069 Uiso 1 1 calc R U . . .
H26B H 0.813615 1.127759 0.205859 0.069 Uiso 1 1 calc R U . . .
H26C H 0.929413 1.178524 0.230144 0.069 Uiso 1 1 calc R U . . .
N1 N 0.74733(8) 0.86100(11) 0.15176(6) 0.0304(2) Uani 1 1 d . . . . .
N2 N 0.95125(8) 0.79039(11) 0.10650(5) 0.0273(2) Uani 1 1 d . . . . .
N3 N 0.83502(9) 0.95735(11) 0.03928(6) 0.0326(2) Uani 1 1 d . . . . .
N4 N 0.92255(8) 0.98885(11) 0.18357(6) 0.0318(2) Uani 1 1 d . . . . .
P1 P 0.84965(2) 0.89828(3) 0.12209(2) 0.02594(10) 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 N1 1.4021(16) . ?
C1 C6 1.4076(17) . ?
C1 C2 1.4189(17) . ?
C2 C3 1.3870(19) . ?
C2 C10 1.5133(19) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.3972(18) . ?
C5 H5 0.9400 . ?
C6 C7 1.5181(18) . ?
C7 C8 1.524(2) . ?
C7 C9 1.536(3) . ?
C7 H7 0.9900 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C12 1.519(3) . ?
C10 C11 1.527(2) . ?
C10 H10 0.9900 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 N3 1.4584(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C15 1.3809(19) . ?
C14 N3 1.4016(16) . ?
C14 C19 1.4037(18) . ?
C15 C16 1.392(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.377(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.395(2) . ?
C17 H17 0.9400 . ?
C18 C19 1.3769(18) . ?
C18 H18 0.9400 . ?
C19 N2 1.4187(16) . ?
C20 C21 1.3790(19) . ?
C20 C25 1.4019(18) . ?
C20 N2 1.4222(16) . ?
C21 C22 1.395(2) . ?
C21 H21 0.9400 . ?
C22 C23 1.375(3) . ?
C22 H22 0.9400 . ?
C23 C24 1.392(2) . ?
C23 H23 0.9400 . ?
C24 C25 1.3815(19) . ?
C24 H24 0.9400 . ?
C25 N4 1.3997(17) . ?
C26 N4 1.4555(17) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
N1 P1 1.5309(11) . ?
N2 P1 1.7095(10) . ?
N3 P1 1.6723(12) . ?
N4 P1 1.6591(11) . ?

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
N1 C1 C6 122.79(11) . . ?
N1 C1 C2 117.65(11) . . ?
C6 C1 C2 119.27(11) . . ?
C3 C2 C1 119.55(12) . . ?
C3 C2 C10 120.03(12) . . ?
C1 C2 C10 120.39(12) . . ?
C4 C3 C2 121.36(13) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.03(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 122.10(13) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 118.63(12) . . ?
C5 C6 C7 118.66(12) . . ?
C1 C6 C7 122.68(11) . . ?
C6 C7 C8 113.38(13) . . ?
C6 C7 C9 109.60(14) . . ?
C8 C7 C9 109.78(14) . . ?
C6 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C9 C7 H7 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 C12 109.97(14) . . ?
C2 C10 C11 113.77(14) . . ?
C12 C10 C11 111.42(15) . . ?
C2 C10 H10 107.1 . . ?
C12 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N3 127.43(13) . . ?
C15 C14 C19 120.36(12) . . ?
N3 C14 C19 112.06(11) . . ?
C14 C15 C16 118.32(14) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 C15 121.44(13) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.38(14) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 118.59(14) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C14 120.91(12) . . ?
C18 C19 N2 127.90(12) . . ?
C14 C19 N2 111.06(11) . . ?
C21 C20 C25 120.89(12) . . ?
C21 C20 N2 128.12(13) . . ?
C25 C20 N2 110.98(11) . . ?
C20 C21 C22 118.43(15) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C23 C22 C21 120.59(15) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 121.32(15) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 118.36(15) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C24 C25 N4 127.42(13) . . ?
C24 C25 C20 120.37(13) . . ?
N4 C25 C20 112.20(11) . . ?
N4 C26 H26A 109.5 . . ?
N4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 N1 P1 137.19(10) . . ?
C19 N2 C20 123.23(10) . . ?
C19 N2 P1 110.55(8) . . ?
C20 N2 P1 110.72(8) . . ?
C14 N3 C13 120.73(12) . . ?
C14 N3 P1 111.86(9) . . ?
C13 N3 P1 123.92(10) . . ?
C25 N4 C26 121.82(12) . . ?
C25 N4 P1 112.56(9) . . ?
C26 N4 P1 124.19(10) . . ?
N1 P1 N4 107.24(6) . . ?
N1 P1 N3 114.72(6) . . ?
N4 P1 N3 119.73(6) . . ?
N1 P1 N2 129.22(6) . . ?
N4 P1 N2 92.84(5) . . ?
N3 P1 N2 92.35(5) . . ?

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
N1 C1 C2 C3 -171.58(12) . . . . ?
C6 C1 C2 C3 2.43(19) . . . . ?
N1 C1 C2 C10 6.53(18) . . . . ?
C6 C1 C2 C10 -179.46(13) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C10 C2 C3 C4 -178.85(14) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C4 C5 C6 C7 -177.90(15) . . . . ?
N1 C1 C6 C5 171.41(13) . . . . ?
C2 C1 C6 C5 -2.28(19) . . . . ?
N1 C1 C6 C7 -10.3(2) . . . . ?
C2 C1 C6 C7 176.02(13) . . . . ?
C5 C6 C7 C8 -48.1(2) . . . . ?
C1 C6 C7 C8 133.57(15) . . . . ?
C5 C6 C7 C9 74.90(17) . . . . ?
C1 C6 C7 C9 -103.39(15) . . . . ?
C3 C2 C10 C12 88.88(18) . . . . ?
C1 C2 C10 C12 -89.21(17) . . . . ?
C3 C2 C10 C11 -36.9(2) . . . . ?
C1 C2 C10 C11 145.00(15) . . . . ?
N3 C14 C15 C16 -175.22(13) . . . . ?
C19 C14 C15 C16 -0.16(19) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C18 1.2(2) . . . . ?
C16 C17 C18 C19 -0.5(2) . . . . ?
C17 C18 C19 C14 -0.4(2) . . . . ?
C17 C18 C19 N2 175.06(12) . . . . ?
C15 C14 C19 C18 0.79(19) . . . . ?
N3 C14 C19 C18 176.56(12) . . . . ?
C15 C14 C19 N2 -175.40(11) . . . . ?
N3 C14 C19 N2 0.37(15) . . . . ?
C25 C20 C21 C22 -0.2(2) . . . . ?
N2 C20 C21 C22 -179.86(14) . . . . ?
C20 C21 C22 C23 1.4(3) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C23 C24 C25 N4 -178.88(14) . . . . ?
C23 C24 C25 C20 2.0(2) . . . . ?
C21 C20 C25 C24 -1.5(2) . . . . ?
N2 C20 C25 C24 178.24(11) . . . . ?
C21 C20 C25 N4 179.26(12) . . . . ?
N2 C20 C25 N4 -1.04(15) . . . . ?
C6 C1 N1 P1 65.28(19) . . . . ?
C2 C1 N1 P1 -120.93(13) . . . . ?
C18 C19 N2 C20 59.29(18) . . . . ?
C14 C19 N2 C20 -124.86(12) . . . . ?
C18 C19 N2 P1 -166.50(11) . . . . ?
C14 C19 N2 P1 9.35(12) . . . . ?
C21 C20 N2 C19 -50.82(19) . . . . ?
C25 C20 N2 C19 129.51(12) . . . . ?
C21 C20 N2 P1 175.03(12) . . . . ?
C25 C20 N2 P1 -4.64(13) . . . . ?
C15 C14 N3 C13 5.5(2) . . . . ?
C19 C14 N3 C13 -169.95(12) . . . . ?
C15 C14 N3 P1 165.16(11) . . . . ?
C19 C14 N3 P1 -10.24(14) . . . . ?
C24 C25 N4 C26 -5.8(2) . . . . ?
C20 C25 N4 C26 173.44(12) . . . . ?
C24 C25 N4 P1 -172.69(11) . . . . ?
C20 C25 N4 P1 6.53(14) . . . . ?
C1 N1 P1 N4 163.08(13) . . . . ?
C1 N1 P1 N3 27.48(16) . . . . ?
C1 N1 P1 N2 -88.25(15) . . . . ?
C25 N4 P1 N1 124.83(9) . . . . ?
C26 N4 P1 N1 -41.72(13) . . . . ?
C25 N4 P1 N3 -102.22(10) . . . . ?
C26 N4 P1 N3 91.23(13) . . . . ?
C25 N4 P1 N2 -7.88(9) . . . . ?
C26 N4 P1 N2 -174.43(12) . . . . ?
C14 N3 P1 N1 -122.31(9) . . . . ?
C13 N3 P1 N1 36.63(14) . . . . ?
C14 N3 P1 N4 108.00(10) . . . . ?
C13 N3 P1 N4 -93.05(13) . . . . ?
C14 N3 P1 N2 13.38(10) . . . . ?
C13 N3 P1 N2 172.33(12) . . . . ?
C19 N2 P1 N1 111.98(9) . . . . ?
C20 N2 P1 N1 -107.88(9) . . . . ?
C19 N2 P1 N4 -132.96(8) . . . . ?
C20 N2 P1 N4 7.17(9) . . . . ?
C19 N2 P1 N3 -13.03(9) . . . . ?
C20 N2 P1 N3 127.10(9) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_3prime_1821120
_database_code_depnum_ccdc_archive 'CCDC 1821120'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H74 N4 O4 P2'
_chemical_formula_weight         833.08

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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'

_cell_length_a                   27.535(6)
_cell_length_b                   11.390(2)
_cell_length_c                   20.157(4)
_cell_angle_alpha                90
_cell_angle_beta                 129.45(3)
_cell_angle_gamma                90
_cell_volume                     4882(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1808
_cell_measurement_theta_min      2.274
_cell_measurement_theta_max      23.213

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19206
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.916
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4252
_reflns_number_gt                3501
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0779P)²+15.7388P] 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         4252
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.2046
_refine_ls_wR_factor_gt          0.1978
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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 -0.07576(15) 0.9779(3) 0.5890(2) 0.0344(8) Uani 1 1 d . . . . .
C2 C -0.11590(15) 0.8930(3) 0.5275(2) 0.0398(8) Uani 1 1 d . . . . .
C3 C -0.16222(18) 0.9295(4) 0.4424(2) 0.0514(10) Uani 1 1 d . . . . .
H3 H -0.189558 0.873956 0.400994 0.062 Uiso 1 1 calc R U . . .
C4 C -0.16844(19) 1.0436(4) 0.4184(2) 0.0543(11) Uani 1 1 d . . . . .
H4 H -0.200571 1.066052 0.361892 0.065 Uiso 1 1 calc R U . . .
C5 C -0.12649(18) 1.1256(4) 0.4789(2) 0.0497(10) Uani 1 1 d . . . . .
H5 H -0.129672 1.203145 0.461992 0.060 Uiso 1 1 calc R U . . .
C6 C -0.07965(16) 1.0951(3) 0.5643(2) 0.0386(8) Uani 1 1 d . . . . .
C7 C -0.03392(19) 1.1914(3) 0.6243(2) 0.0476(9) Uani 1 1 d . . . . .
H7 H -0.002852 1.156522 0.681315 0.057 Uiso 1 1 calc R U . . .
C8 C -0.0663(3) 1.2909(4) 0.6333(4) 0.0732(14) Uani 1 1 d . . . . .
H8A H -0.035780 1.349441 0.671557 0.110 Uiso 1 1 calc R U . . .
H8B H -0.097841 1.325400 0.577964 0.110 Uiso 1 1 calc R U . . .
H8C H -0.085632 1.260656 0.655972 0.110 Uiso 1 1 calc R U . . .
C9 C 0.0016(2) 1.2402(4) 0.5948(3) 0.0645(12) Uani 1 1 d . . . . .
H9A H 0.021857 1.176971 0.589346 0.097 Uiso 1 1 calc R U . . .
H9B H -0.027566 1.278526 0.540312 0.097 Uiso 1 1 calc R U . . .
H9C H 0.032633 1.295656 0.636407 0.097 Uiso 1 1 calc R U . . .
C10 C -0.11164(18) 0.7632(4) 0.5466(2) 0.0478(9) Uani 1 1 d . . . . .
H10 H -0.076261 0.751217 0.607725 0.057 Uiso 1 1 calc R U . . .
C11 C -0.1716(2) 0.7209(5) 0.5291(3) 0.0733(14) Uani 1 1 d . . . . .
H11A H -0.168107 0.638565 0.541575 0.110 Uiso 1 1 calc R U . . .
H11B H -0.177164 0.763429 0.565007 0.110 Uiso 1 1 calc R U . . .
H11C H -0.207092 0.734275 0.469890 0.110 Uiso 1 1 calc R U . . .
C12 C -0.0996(3) 0.6899(4) 0.4944(3) 0.0743(14) Uani 1 1 d . . . . .
H12A H -0.097175 0.608276 0.508138 0.112 Uiso 1 1 calc R U . . .
H12B H -0.133368 0.701548 0.434143 0.112 Uiso 1 1 calc R U . . .
H12C H -0.060673 0.713929 0.508166 0.112 Uiso 1 1 calc R U . . .
C13 C 0.10826(16) 1.0191(3) 0.6977(2) 0.0410(8) Uani 1 1 d . . . . .
H13 H 0.123893 1.028383 0.668523 0.049 Uiso 1 1 calc R U . . .
C14 C 0.13536(16) 1.0656(3) 0.7741(2) 0.0387(8) Uani 1 1 d . . . . .
C15 C 0.19607(18) 1.1313(4) 0.8350(3) 0.0527(10) Uani 1 1 d . . . . .
C16 C 0.1849(3) 1.2607(6) 0.8351(6) 0.140(3) Uani 1 1 d . . . . .
H16A H 0.224512 1.300107 0.874587 0.210 Uiso 1 1 calc R U . . .
H16B H 0.163255 1.291827 0.778394 0.210 Uiso 1 1 calc R U . . .
H16C H 0.159807 1.272648 0.852330 0.210 Uiso 1 1 calc R U . . .
C17 C 0.2296(3) 1.0847(8) 0.9242(4) 0.142(4) Uani 1 1 d . . . . .
H17A H 0.268549 1.126159 0.963741 0.213 Uiso 1 1 calc R U . . .
H17B H 0.203713 1.095589 0.940220 0.213 Uiso 1 1 calc R U . . .
H17C H 0.238053 1.002563 0.925603 0.213 Uiso 1 1 calc R U . . .
C18 C 0.2353(3) 1.1157(8) 0.8074(5) 0.138(4) Uani 1 1 d . . . . .
H18A H 0.274228 1.157556 0.846052 0.207 Uiso 1 1 calc R U . . .
H18B H 0.243856 1.033808 0.808175 0.207 Uiso 1 1 calc R U . . .
H18C H 0.212800 1.145944 0.750230 0.207 Uiso 1 1 calc R U . . .
C19 C 0.05872(16) 0.8373(3) 0.6444(2) 0.0396(8) Uani 1 1 d . . . . .
H19 H 0.053269 0.818181 0.595167 0.047 Uiso 1 1 calc R U . . .
C20 C 0.07237(16) 0.7589(3) 0.7023(2) 0.0381(8) Uani 1 1 d . . . . .
C21 C 0.09200(19) 0.6324(3) 0.7131(3) 0.0481(9) Uani 1 1 d . . . . .
C22 C 0.0591(3) 0.5572(4) 0.7372(4) 0.0710(14) Uani 1 1 d . . . . .
H22A H 0.072159 0.476968 0.743807 0.106 Uiso 1 1 calc R U . . .
H22B H 0.070210 0.585131 0.790167 0.106 Uiso 1 1 calc R U . . .
H22C H 0.014405 0.562498 0.692541 0.106 Uiso 1 1 calc R U . . .
C23 C 0.0770(2) 0.5860(4) 0.6310(3) 0.0677(13) Uani 1 1 d . . . . .
H23A H 0.089827 0.505367 0.638904 0.102 Uiso 1 1 calc R U . . .
H23B H 0.032635 0.591819 0.584510 0.102 Uiso 1 1 calc R U . . .
H23C H 0.099262 0.631632 0.617783 0.102 Uiso 1 1 calc R U . . .
C24 C 0.1638(2) 0.6259(5) 0.7855(3) 0.0727(14) Uani 1 1 d . . . . .
H24A H 0.177369 0.545771 0.793476 0.109 Uiso 1 1 calc R U . . .
H24B H 0.184369 0.672477 0.770090 0.109 Uiso 1 1 calc R U . . .
H24C H 0.174347 0.655317 0.837830 0.109 Uiso 1 1 calc R U . . .
N1 N -0.03222(12) 0.9462(2) 0.67878(17) 0.0311(6) Uani 1 1 d . . . . .
N2 N 0.05314(13) 0.9540(2) 0.66441(17) 0.0340(7) Uani 1 1 d . . . . .
O1 O 0.10116(10) 1.0406(2) 0.80284(15) 0.0360(6) Uani 1 1 d . . . . .
O2 O 0.07394(10) 0.8060(2) 0.76860(14) 0.0357(6) Uani 1 1 d . . . . .
P1 P 0.04602(4) 0.94121(7) 0.74602(5) 0.0292(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.398(5) . ?
C1 C6 1.405(5) . ?
C1 N1 1.444(4) . ?
C2 C3 1.401(5) . ?
C2 C10 1.513(5) . ?
C3 C4 1.358(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.522(5) . ?
C7 C8 1.521(6) . ?
C7 C9 1.535(6) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.530(6) . ?
C10 C12 1.537(6) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.321(5) . ?
C13 N2 1.418(4) . ?
C13 H13 0.9300 . ?
C14 O1 1.413(4) . ?
C14 C15 1.502(5) . ?
C15 C17 1.502(8) . ?
C15 C16 1.506(8) . ?
C15 C18 1.509(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.321(5) . ?
C19 N2 1.425(4) . ?
C19 H19 0.9300 . ?
C20 O2 1.415(4) . ?
C20 C21 1.505(5) . ?
C21 C23 1.525(6) . ?
C21 C22 1.531(6) . ?
C21 C24 1.541(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 P1 1.665(3) . ?
N1 P1 1.783(3) 2_556 ?
N2 P1 1.782(3) . ?
O1 P1 1.640(2) . ?
O2 P1 1.651(2) . ?
P1 P1 2.6392(17) 2_556 ?

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 C6 120.2(3) . . ?
C2 C1 N1 119.9(3) . . ?
C6 C1 N1 119.8(3) . . ?
C1 C2 C3 118.2(4) . . ?
C1 C2 C10 124.1(3) . . ?
C3 C2 C10 117.7(3) . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 116.9(3) . . ?
C1 C6 C7 124.4(3) . . ?
C8 C7 C6 112.3(4) . . ?
C8 C7 C9 110.0(4) . . ?
C6 C7 C9 111.2(3) . . ?
C8 C7 H7 107.7 . . ?
C6 C7 H7 107.7 . . ?
C9 C7 H7 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 C11 110.6(4) . . ?
C2 C10 C12 111.8(4) . . ?
C11 C10 C12 110.0(4) . . ?
C2 C10 H10 108.1 . . ?
C11 C10 H10 108.1 . . ?
C12 C10 H10 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N2 113.8(3) . . ?
C14 C13 H13 123.1 . . ?
N2 C13 H13 123.1 . . ?
C13 C14 O1 111.5(3) . . ?
C13 C14 C15 131.6(3) . . ?
O1 C14 C15 116.8(3) . . ?
C14 C15 C17 108.8(4) . . ?
C14 C15 C16 111.5(4) . . ?
C17 C15 C16 108.4(6) . . ?
C14 C15 C18 109.0(4) . . ?
C17 C15 C18 111.1(6) . . ?
C16 C15 C18 108.0(5) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 N2 113.7(3) . . ?
C20 C19 H19 123.2 . . ?
N2 C19 H19 123.2 . . ?
C19 C20 O2 113.5(3) . . ?
C19 C20 C21 130.5(3) . . ?
O2 C20 C21 115.7(3) . . ?
C20 C21 C23 110.5(3) . . ?
C20 C21 C22 110.6(3) . . ?
C23 C21 C22 110.1(4) . . ?
C20 C21 C24 108.1(3) . . ?
C23 C21 C24 108.0(4) . . ?
C22 C21 C24 109.6(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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 P1 130.1(2) . . ?
C1 N1 P1 128.1(2) . 2_556 ?
P1 N1 P1 99.87(14) . 2_556 ?
C13 N2 C19 110.3(3) . . ?
C13 N2 P1 108.5(2) . . ?
C19 N2 P1 106.3(2) . . ?
C14 O1 P1 114.5(2) . . ?
C20 O2 P1 111.3(2) . . ?
O1 P1 O2 112.90(13) . . ?
O1 P1 N1 133.63(13) . . ?
O2 P1 N1 113.05(13) . . ?
O1 P1 N2 89.56(12) . . ?
O2 P1 N2 91.45(12) . . ?
N1 P1 N2 95.17(13) . . ?
O1 P1 N1 89.26(12) . 2_556 ?
O2 P1 N1 96.25(12) . 2_556 ?
N1 P1 N1 80.00(14) . 2_556 ?
N2 P1 N1 172.04(13) . 2_556 ?
O1 P1 P1 117.15(9) . 2_556 ?
O2 P1 P1 106.28(8) . 2_556 ?
N1 P1 P1 41.71(9) . 2_556 ?
N2 P1 P1 136.83(11) . 2_556 ?
N1 P1 P1 38.42(9) 2_556 2_556 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -4.0(5) . . . . ?
N1 C1 C2 C3 173.0(3) . . . . ?
C6 C1 C2 C10 174.6(3) . . . . ?
N1 C1 C2 C10 -8.4(5) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C10 C2 C3 C4 -177.9(4) . . . . ?
C2 C3 C4 C5 2.4(6) . . . . ?
C3 C4 C5 C6 -2.6(6) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C4 C5 C6 C7 176.8(4) . . . . ?
C2 C1 C6 C5 3.9(5) . . . . ?
N1 C1 C6 C5 -173.1(3) . . . . ?
C2 C1 C6 C7 -173.3(3) . . . . ?
N1 C1 C6 C7 9.7(5) . . . . ?
C5 C6 C7 C8 63.8(5) . . . . ?
C1 C6 C7 C8 -119.0(4) . . . . ?
C5 C6 C7 C9 -59.9(5) . . . . ?
C1 C6 C7 C9 117.3(4) . . . . ?
C1 C2 C10 C11 117.2(4) . . . . ?
C3 C2 C10 C11 -64.2(5) . . . . ?
C1 C2 C10 C12 -119.9(4) . . . . ?
C3 C2 C10 C12 58.8(5) . . . . ?
N2 C13 C14 O1 -1.5(4) . . . . ?
N2 C13 C14 C15 174.3(4) . . . . ?
C13 C14 C15 C17 -135.1(6) . . . . ?
O1 C14 C15 C17 40.5(6) . . . . ?
C13 C14 C15 C16 105.4(6) . . . . ?
O1 C14 C15 C16 -79.0(6) . . . . ?
C13 C14 C15 C18 -13.8(7) . . . . ?
O1 C14 C15 C18 161.8(5) . . . . ?
N2 C19 C20 O2 4.4(4) . . . . ?
N2 C19 C20 C21 -169.2(3) . . . . ?
C19 C20 C21 C23 -16.7(6) . . . . ?
O2 C20 C21 C23 169.7(3) . . . . ?
C19 C20 C21 C22 -138.9(4) . . . . ?
O2 C20 C21 C22 47.6(5) . . . . ?
C19 C20 C21 C24 101.2(5) . . . . ?
O2 C20 C21 C24 -72.3(4) . . . . ?
C2 C1 N1 P1 113.3(3) . . . . ?
C6 C1 N1 P1 -69.6(4) . . . . ?
C2 C1 N1 P1 -85.8(4) . . . 2_556 ?
C6 C1 N1 P1 91.3(4) . . . 2_556 ?
C14 C13 N2 C19 -124.0(3) . . . . ?
C14 C13 N2 P1 -8.0(4) . . . . ?
C20 C19 N2 C13 102.0(3) . . . . ?
C20 C19 N2 P1 -15.5(4) . . . . ?
C13 C14 O1 P1 11.6(4) . . . . ?
C15 C14 O1 P1 -164.9(3) . . . . ?
C19 C20 O2 P1 10.0(4) . . . . ?
C21 C20 O2 P1 -175.3(2) . . . . ?
C14 O1 P1 O2 77.9(2) . . . . ?
C14 O1 P1 N1 -110.2(3) . . . . ?
C14 O1 P1 N2 -13.5(2) . . . . ?
C14 O1 P1 N1 174.4(2) . . . 2_556 ?
C14 O1 P1 P1 -158.2(2) . . . 2_556 ?
C20 O2 P1 O1 -106.2(2) . . . . ?
C20 O2 P1 N1 80.2(2) . . . . ?
C20 O2 P1 N2 -16.0(2) . . . . ?
C20 O2 P1 N1 162.0(2) . . . 2_556 ?
C20 O2 P1 P1 124.08(19) . . . 2_556 ?
C1 N1 P1 O1 81.9(3) . . . . ?
P1 N1 P1 O1 -82.98(19) 2_556 . . . ?
C1 N1 P1 O2 -106.3(3) . . . . ?
P1 N1 P1 O2 88.88(15) 2_556 . . . ?
C1 N1 P1 N2 -12.5(3) . . . . ?
P1 N1 P1 N2 -177.32(13) 2_556 . . . ?
C1 N1 P1 N1 161.1(2) . . . 2_556 ?
P1 N1 P1 N1 -3.71(18) 2_556 . . 2_556 ?
C1 N1 P1 P1 164.8(4) . . . 2_556 ?
C13 N2 P1 O1 12.0(2) . . . . ?
C19 N2 P1 O1 130.6(2) . . . . ?
C13 N2 P1 O2 -100.9(2) . . . . ?
C19 N2 P1 O2 17.7(2) . . . . ?
C13 N2 P1 N1 145.8(2) . . . . ?
C19 N2 P1 N1 -95.6(2) . . . . ?
C13 N2 P1 P1 143.22(18) . . . 2_556 ?
C19 N2 P1 P1 -98.2(2) . . . 2_556 ?

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.062



####################################################################### 
# 
# 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_10prime_1821121
_database_code_depnum_ccdc_archive 'CCDC 1821121'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H54 N4 O4 P2'
_chemical_formula_weight         692.79

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'
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                   9.2449(12)
_cell_length_b                   21.052(3)
_cell_length_c                   20.977(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.271(2)
_cell_angle_gamma                90
_cell_volume                     4071.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5650
_cell_measurement_theta_min      2.411
_cell_measurement_theta_max      25.944

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9544
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23546
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.935
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7120
_reflns_number_gt                5610
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0530P)²+8.7989P] 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         7120
_refine_ls_number_parameters     446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2112
_refine_ls_wR_factor_gt          0.2038
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_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 0.8480(5) 0.0568(2) 0.3044(2) 0.0509(11) Uani 1 1 d . . . . .
H1 H 0.945287 0.053346 0.318888 0.061 Uiso 1 1 calc R U . . .
C2 C 0.7412(5) 0.0318(2) 0.3342(2) 0.0493(11) Uani 1 1 d . . . . .
C3 C 0.7363(6) -0.0019(3) 0.3969(2) 0.0676(14) Uani 1 1 d . . . . .
C4 C 0.6435(13) -0.0600(4) 0.3884(4) 0.187(6) Uani 1 1 d . . . . .
H4A H 0.549490 -0.048322 0.369475 0.280 Uiso 1 1 calc R U . . .
H4B H 0.633490 -0.079432 0.429216 0.280 Uiso 1 1 calc R U . . .
H4C H 0.687975 -0.089522 0.360941 0.280 Uiso 1 1 calc R U . . .
C5 C 0.6734(11) 0.0409(5) 0.4447(4) 0.157(4) Uani 1 1 d . . . . .
H5A H 0.723601 0.080888 0.445839 0.236 Uiso 1 1 calc R U . . .
H5B H 0.683933 0.021584 0.486238 0.236 Uiso 1 1 calc R U . . .
H5C H 0.572395 0.047812 0.432686 0.236 Uiso 1 1 calc R U . . .
C6 C 0.8879(8) -0.0206(5) 0.4217(4) 0.143(4) Uani 1 1 d . . . . .
H6A H 0.930320 -0.046973 0.390679 0.214 Uiso 1 1 calc R U . . .
H6B H 0.883996 -0.043675 0.460987 0.214 Uiso 1 1 calc R U . . .
H6C H 0.945838 0.016872 0.429044 0.214 Uiso 1 1 calc R U . . .
C7 C 0.8589(5) 0.0764(2) 0.1897(2) 0.0498(11) Uani 1 1 d . . . . .
H7 H 0.957667 0.077176 0.184030 0.060 Uiso 1 1 calc R U . . .
C8 C 0.7578(5) 0.0630(2) 0.1442(2) 0.0506(11) Uani 1 1 d . . . . .
C9 C 0.7631(6) 0.0504(3) 0.0739(2) 0.0676(14) Uani 1 1 d . . . . .
C10 C 0.7216(9) -0.0183(4) 0.0604(3) 0.118(3) Uani 1 1 d . . . . .
H10A H 0.786978 -0.045790 0.085090 0.177 Uiso 1 1 calc R U . . .
H10B H 0.727272 -0.027072 0.015725 0.177 Uiso 1 1 calc R U . . .
H10C H 0.624330 -0.025561 0.071808 0.177 Uiso 1 1 calc R U . . .
C11 C 0.6569(7) 0.0940(4) 0.0358(3) 0.101(2) Uani 1 1 d . . . . .
H11A H 0.560859 0.087237 0.048973 0.152 Uiso 1 1 calc R U . . .
H11B H 0.658452 0.084647 -0.008967 0.152 Uiso 1 1 calc R U . . .
H11C H 0.684492 0.137443 0.043333 0.152 Uiso 1 1 calc R U . . .
C12 C 0.9169(7) 0.0632(4) 0.0546(3) 0.106(2) Uani 1 1 d . . . . .
H12A H 0.942193 0.106712 0.063446 0.159 Uiso 1 1 calc R U . . .
H12B H 0.921047 0.055086 0.009703 0.159 Uiso 1 1 calc R U . . .
H12C H 0.984040 0.035822 0.078439 0.159 Uiso 1 1 calc R U . . .
C13 C 0.6757(4) 0.21688(18) 0.2596(2) 0.0407(9) Uani 1 1 d . . . . .
C14 C 0.7032(5) 0.2422(2) 0.3200(2) 0.0554(12) Uani 1 1 d . . . . .
H14 H 0.659271 0.224825 0.354475 0.066 Uiso 1 1 calc R U . . .
C15 C 0.7960(6) 0.2934(3) 0.3294(3) 0.0718(15) Uani 1 1 d . . . . .
H15 H 0.812311 0.310285 0.370258 0.086 Uiso 1 1 calc R U . . .
C16 C 0.8638(6) 0.3196(2) 0.2809(3) 0.0722(16) Uani 1 1 d . . . . .
C17 C 0.8386(6) 0.2935(3) 0.2211(3) 0.0765(17) Uani 1 1 d . . . . .
H17 H 0.886407 0.310033 0.187393 0.092 Uiso 1 1 calc R U . . .
C18 C 0.7437(5) 0.2431(2) 0.2098(3) 0.0588(13) Uani 1 1 d . . . . .
H18 H 0.725984 0.227142 0.168613 0.071 Uiso 1 1 calc R U . . .
C19 C 0.9693(8) 0.3753(3) 0.2909(5) 0.126(3) Uani 1 1 d . . . . .
H19A H 1.005533 0.386854 0.250792 0.188 Uiso 1 1 calc R U . . .
H19B H 0.919887 0.410934 0.307847 0.188 Uiso 1 1 calc R U . . .
H19C H 1.048810 0.363098 0.320438 0.188 Uiso 1 1 calc R U . . .
C20 C 0.3216(4) 0.03634(18) 0.2249(2) 0.0402(9) Uani 1 1 d . . . . .
C21 C 0.2842(5) 0.0084(2) 0.1664(2) 0.0579(12) Uani 1 1 d . . . . .
H21 H 0.321641 0.024025 0.129587 0.070 Uiso 1 1 calc R U . . .
C22 C 0.1910(6) -0.0430(3) 0.1629(3) 0.0757(16) Uani 1 1 d . . . . .
H22 H 0.166468 -0.061508 0.123309 0.091 Uiso 1 1 calc R U . . .
C23 C 0.1339(6) -0.0672(2) 0.2159(4) 0.0751(17) Uani 1 1 d . . . . .
C24 C 0.1718(6) -0.0396(3) 0.2727(3) 0.0736(16) Uani 1 1 d . . . . .
H24 H 0.133905 -0.055457 0.309369 0.088 Uiso 1 1 calc R U . . .
C25 C 0.2660(5) 0.0120(2) 0.2781(2) 0.0596(13) Uani 1 1 d . . . . .
H25 H 0.290984 0.029843 0.317925 0.071 Uiso 1 1 calc R U . . .
C26 C 0.0287(8) -0.1234(3) 0.2108(5) 0.133(3) Uani 1 1 d . . . . .
H26A H 0.080262 -0.161841 0.222336 0.199 Uiso 1 1 calc R U . . .
H26B H -0.013404 -0.126792 0.167754 0.199 Uiso 1 1 calc R U . . .
H26C H -0.046585 -0.116932 0.239289 0.199 Uiso 1 1 calc R U . . .
C27 C 0.1493(5) 0.1979(2) 0.1756(2) 0.0487(11) Uani 1 1 d . . . . .
H27 H 0.052188 0.201984 0.161169 0.058 Uiso 1 1 calc R U . . .
C28 C 0.2563(5) 0.2234(2) 0.1463(2) 0.0490(11) Uani 1 1 d . . . . .
C29 C 0.2624(6) 0.2587(3) 0.0844(3) 0.0688(15) Uani 1 1 d . . . . .
C30 C 0.3315(10) 0.2159(4) 0.0366(3) 0.128(3) Uani 1 1 d . . . . .
H30A H 0.429611 0.206507 0.051972 0.192 Uiso 1 1 calc R U . . .
H30B H 0.331199 0.237124 -0.003891 0.192 Uiso 1 1 calc R U . . .
H30C H 0.277325 0.177087 0.031680 0.192 Uiso 1 1 calc R U . . .
C31 C 0.3505(10) 0.3185(3) 0.0940(4) 0.130(3) Uani 1 1 d . . . . .
H31A H 0.307050 0.345420 0.124244 0.195 Uiso 1 1 calc R U . . .
H31B H 0.353156 0.340409 0.054001 0.195 Uiso 1 1 calc R U . . .
H31C H 0.447454 0.307844 0.110005 0.195 Uiso 1 1 calc R U . . .
C32 C 0.1083(8) 0.2739(5) 0.0585(4) 0.152(4) Uani 1 1 d . . . . .
H32A H 0.053035 0.235343 0.054271 0.228 Uiso 1 1 calc R U . . .
H32B H 0.110223 0.293955 0.017504 0.228 Uiso 1 1 calc R U . . .
H32C H 0.064356 0.302042 0.087502 0.228 Uiso 1 1 calc R U . . .
C33 C 0.1388(4) 0.1766(2) 0.2894(2) 0.0480(11) Uani 1 1 d . . . . .
H33 H 0.039887 0.176223 0.294977 0.058 Uiso 1 1 calc R U . . .
C34 C 0.2383(5) 0.1895(2) 0.3354(2) 0.0477(10) Uani 1 1 d . . . . .
C35 C 0.2340(6) 0.2005(3) 0.4056(2) 0.0653(14) Uani 1 1 d . . . . .
C36 C 0.2961(10) 0.2657(3) 0.4230(3) 0.117(3) Uani 1 1 d . . . . .
H36A H 0.391684 0.269191 0.408241 0.176 Uiso 1 1 calc R U . . .
H36B H 0.301208 0.271008 0.468521 0.176 Uiso 1 1 calc R U . . .
H36C H 0.234790 0.297905 0.403062 0.176 Uiso 1 1 calc R U . . .
C37 C 0.0764(7) 0.1959(5) 0.4234(3) 0.140(4) Uani 1 1 d . . . . .
H37A H 0.019435 0.228113 0.401009 0.210 Uiso 1 1 calc R U . . .
H37B H 0.073023 0.201822 0.468601 0.210 Uiso 1 1 calc R U . . .
H37C H 0.038188 0.154770 0.411593 0.210 Uiso 1 1 calc R U . . .
C38 C 0.3236(7) 0.1508(3) 0.4426(3) 0.0892(19) Uani 1 1 d . . . . .
H38A H 0.282337 0.109616 0.433930 0.134 Uiso 1 1 calc R U . . .
H38B H 0.324357 0.159641 0.487497 0.134 Uiso 1 1 calc R U . . .
H38C H 0.421151 0.151736 0.429745 0.134 Uiso 1 1 calc R U . . .
N1 N 0.5776(3) 0.16449(15) 0.24904(16) 0.0383(8) Uani 1 1 d . . . . .
N2 N 0.4206(3) 0.08896(15) 0.23031(16) 0.0388(8) Uani 1 1 d . . . . .
N3 N 0.7988(3) 0.08959(16) 0.24811(16) 0.0422(8) Uani 1 1 d . . . . .
N4 N 0.1971(3) 0.16362(16) 0.23115(16) 0.0413(8) Uani 1 1 d . . . . .
O1 O 0.6061(3) 0.04276(13) 0.30187(14) 0.0481(7) Uani 1 1 d . . . . .
O2 O 0.6170(3) 0.06252(14) 0.16590(14) 0.0472(7) Uani 1 1 d . . . . .
O3 O 0.3912(3) 0.21288(13) 0.17893(13) 0.0453(7) Uani 1 1 d . . . . .
O4 O 0.3791(3) 0.18999(14) 0.31394(13) 0.0454(7) Uani 1 1 d . . . . .
P1 P 0.60960(10) 0.08889(5) 0.23920(5) 0.0353(3) Uani 1 1 d . . . . .
P2 P 0.38775(10) 0.16499(5) 0.24050(5) 0.0348(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.318(6) . ?
C1 N3 1.414(5) . ?
C1 H1 0.9300 . ?
C2 O1 1.395(5) . ?
C2 C3 1.498(7) . ?
C3 C4 1.497(9) . ?
C3 C5 1.498(9) . ?
C3 C6 1.510(8) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.315(6) . ?
C7 N3 1.410(5) . ?
C7 H7 0.9300 . ?
C8 O2 1.411(5) . ?
C8 C9 1.504(7) . ?
C9 C10 1.519(9) . ?
C9 C11 1.525(8) . ?
C9 C12 1.531(8) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.375(6) . ?
C13 C14 1.381(6) . ?
C13 N1 1.435(5) . ?
C14 C15 1.382(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.353(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(8) . ?
C16 C19 1.529(7) . ?
C17 C18 1.385(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.362(6) . ?
C20 C21 1.382(6) . ?
C20 N2 1.436(5) . ?
C21 C22 1.380(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.349(8) . ?
C23 C26 1.531(7) . ?
C24 C25 1.391(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.318(6) . ?
C27 N4 1.413(5) . ?
C27 H27 0.9300 . ?
C28 O3 1.395(5) . ?
C28 C29 1.499(6) . ?
C29 C31 1.505(9) . ?
C29 C32 1.520(8) . ?
C29 C30 1.524(9) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.310(6) . ?
C33 N4 1.400(5) . ?
C33 H33 0.9300 . ?
C34 O4 1.409(5) . ?
C34 C35 1.496(6) . ?
C35 C38 1.511(8) . ?
C35 C36 1.521(9) . ?
C35 C37 1.533(8) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
N1 P1 1.635(3) . ?
N1 P2 1.751(3) . ?
N2 P2 1.646(3) . ?
N2 P1 1.744(3) . ?
N3 P1 1.746(3) . ?
N4 P2 1.759(3) . ?
O1 P1 1.637(3) . ?
O2 P1 1.641(3) . ?
O3 P2 1.641(3) . ?
O4 P2 1.636(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
C2 C1 N3 112.7(4) . . ?
C2 C1 H1 123.7 . . ?
N3 C1 H1 123.7 . . ?
C1 C2 O1 112.2(4) . . ?
C1 C2 C3 132.8(4) . . ?
O1 C2 C3 114.9(4) . . ?
C4 C3 C5 109.0(7) . . ?
C4 C3 C2 109.7(5) . . ?
C5 C3 C2 109.9(5) . . ?
C4 C3 C6 109.7(7) . . ?
C5 C3 C6 108.9(6) . . ?
C2 C3 C6 109.7(5) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N3 111.6(4) . . ?
C8 C7 H7 124.2 . . ?
N3 C7 H7 124.2 . . ?
C7 C8 O2 113.0(4) . . ?
C7 C8 C9 132.6(4) . . ?
O2 C8 C9 114.4(4) . . ?
C8 C9 C10 108.9(5) . . ?
C8 C9 C11 110.0(4) . . ?
C10 C9 C11 109.3(6) . . ?
C8 C9 C12 109.1(5) . . ?
C10 C9 C12 110.2(5) . . ?
C11 C9 C12 109.3(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.6(4) . . ?
C18 C13 N1 120.7(4) . . ?
C14 C13 N1 120.7(4) . . ?
C13 C14 C15 120.1(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 122.0(5) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 117.8(5) . . ?
C15 C16 C19 122.4(6) . . ?
C17 C16 C19 119.8(6) . . ?
C16 C17 C18 121.8(5) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C17 119.7(5) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.8(4) . . ?
C25 C20 N2 120.2(4) . . ?
C21 C20 N2 120.9(4) . . ?
C22 C21 C20 119.7(5) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 121.8(5) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C24 C23 C22 117.9(5) . . ?
C24 C23 C26 121.1(6) . . ?
C22 C23 C26 121.0(6) . . ?
C23 C24 C25 121.8(5) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C20 C25 C24 120.0(5) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 N4 113.2(4) . . ?
C28 C27 H27 123.4 . . ?
N4 C27 H27 123.4 . . ?
C27 C28 O3 112.3(4) . . ?
C27 C28 C29 133.1(4) . . ?
O3 C28 C29 114.5(4) . . ?
C28 C29 C31 110.7(5) . . ?
C28 C29 C32 108.6(5) . . ?
C31 C29 C32 110.8(6) . . ?
C28 C29 C30 108.7(5) . . ?
C31 C29 C30 109.5(6) . . ?
C32 C29 C30 108.5(6) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 N4 112.8(4) . . ?
C34 C33 H33 123.6 . . ?
N4 C33 H33 123.6 . . ?
C33 C34 O4 112.5(4) . . ?
C33 C34 C35 133.5(4) . . ?
O4 C34 C35 114.0(4) . . ?
C34 C35 C38 110.1(4) . . ?
C34 C35 C36 109.8(5) . . ?
C38 C35 C36 108.6(5) . . ?
C34 C35 C37 108.9(5) . . ?
C38 C35 C37 109.0(5) . . ?
C36 C35 C37 110.4(6) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C13 N1 P1 130.5(3) . . ?
C13 N1 P2 128.9(3) . . ?
P1 N1 P2 100.50(17) . . ?
C20 N2 P2 129.6(3) . . ?
C20 N2 P1 129.5(3) . . ?
P2 N2 P1 100.36(17) . . ?
C7 N3 C1 120.5(3) . . ?
C7 N3 P1 111.2(3) . . ?
C1 N3 P1 110.1(3) . . ?
C33 N4 C27 120.2(3) . . ?
C33 N4 P2 110.3(3) . . ?
C27 N4 P2 109.4(3) . . ?
C2 O1 P1 114.8(3) . . ?
C8 O2 P1 113.8(3) . . ?
C28 O3 P2 114.5(3) . . ?
C34 O4 P2 114.2(3) . . ?
N1 P1 O1 117.50(17) . . ?
N1 P1 O2 117.93(17) . . ?
O1 P1 O2 123.82(16) . . ?
N1 P1 N2 79.84(15) . . ?
O1 P1 N2 90.40(15) . . ?
O2 P1 N2 90.66(15) . . ?
N1 P1 N3 99.64(16) . . ?
O1 P1 N3 89.91(15) . . ?
O2 P1 N3 89.52(15) . . ?
N2 P1 N3 179.47(17) . . ?
O4 P2 O3 123.29(16) . . ?
O4 P2 N2 117.23(16) . . ?
O3 P2 N2 118.74(17) . . ?
O4 P2 N1 91.40(15) . . ?
O3 P2 N1 90.34(15) . . ?
N2 P2 N1 79.31(15) . . ?
O4 P2 N4 89.50(15) . . ?
O3 P2 N4 90.04(15) . . ?
N2 P2 N4 99.34(16) . . ?
N1 P2 N4 178.61(17) . . ?

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
N3 C1 C2 O1 1.3(6) . . . . ?
N3 C1 C2 C3 -174.3(5) . . . . ?
C1 C2 C3 C4 -134.5(7) . . . . ?
O1 C2 C3 C4 50.0(8) . . . . ?
C1 C2 C3 C5 105.7(7) . . . . ?
O1 C2 C3 C5 -69.8(7) . . . . ?
C1 C2 C3 C6 -13.9(9) . . . . ?
O1 C2 C3 C6 170.6(6) . . . . ?
N3 C7 C8 O2 -2.5(5) . . . . ?
N3 C7 C8 C9 175.0(5) . . . . ?
C7 C8 C9 C10 113.4(7) . . . . ?
O2 C8 C9 C10 -69.1(6) . . . . ?
C7 C8 C9 C11 -126.8(6) . . . . ?
O2 C8 C9 C11 50.8(6) . . . . ?
C7 C8 C9 C12 -6.9(8) . . . . ?
O2 C8 C9 C12 170.6(5) . . . . ?
C18 C13 C14 C15 0.8(7) . . . . ?
N1 C13 C14 C15 -178.9(4) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
C14 C15 C16 C17 -0.4(8) . . . . ?
C14 C15 C16 C19 -178.6(5) . . . . ?
C15 C16 C17 C18 1.9(8) . . . . ?
C19 C16 C17 C18 -179.9(6) . . . . ?
C14 C13 C18 C17 0.7(7) . . . . ?
N1 C13 C18 C17 -179.7(4) . . . . ?
C16 C17 C18 C13 -2.1(8) . . . . ?
C25 C20 C21 C22 0.6(7) . . . . ?
N2 C20 C21 C22 178.7(4) . . . . ?
C20 C21 C22 C23 0.0(8) . . . . ?
C21 C22 C23 C24 -0.3(9) . . . . ?
C21 C22 C23 C26 179.0(6) . . . . ?
C22 C23 C24 C25 0.0(9) . . . . ?
C26 C23 C24 C25 -179.3(6) . . . . ?
C21 C20 C25 C24 -0.9(7) . . . . ?
N2 C20 C25 C24 -179.1(4) . . . . ?
C23 C24 C25 C20 0.6(8) . . . . ?
N4 C27 C28 O3 -2.8(6) . . . . ?
N4 C27 C28 C29 174.3(5) . . . . ?
C27 C28 C29 C31 131.8(7) . . . . ?
O3 C28 C29 C31 -51.2(7) . . . . ?
C27 C28 C29 C32 10.0(9) . . . . ?
O3 C28 C29 C32 -173.0(6) . . . . ?
C27 C28 C29 C30 -107.9(7) . . . . ?
O3 C28 C29 C30 69.1(6) . . . . ?
N4 C33 C34 O4 2.9(5) . . . . ?
N4 C33 C34 C35 -173.7(5) . . . . ?
C33 C34 C35 C38 118.6(6) . . . . ?
O4 C34 C35 C38 -57.9(6) . . . . ?
C33 C34 C35 C36 -122.0(6) . . . . ?
O4 C34 C35 C36 61.5(6) . . . . ?
C33 C34 C35 C37 -1.0(9) . . . . ?
O4 C34 C35 C37 -177.5(5) . . . . ?
C18 C13 N1 P1 78.2(5) . . . . ?
C14 C13 N1 P1 -102.2(4) . . . . ?
C18 C13 N1 P2 -99.4(5) . . . . ?
C14 C13 N1 P2 80.2(5) . . . . ?
C25 C20 N2 P2 -77.4(5) . . . . ?
C21 C20 N2 P2 104.5(4) . . . . ?
C25 C20 N2 P1 92.5(5) . . . . ?
C21 C20 N2 P1 -85.7(5) . . . . ?
C8 C7 N3 C1 126.9(4) . . . . ?
C8 C7 N3 P1 -4.0(5) . . . . ?
C2 C1 N3 C7 -128.6(4) . . . . ?
C2 C1 N3 P1 2.9(5) . . . . ?
C34 C33 N4 C27 -125.7(4) . . . . ?
C34 C33 N4 P2 3.0(5) . . . . ?
C28 C27 N4 C33 127.3(4) . . . . ?
C28 C27 N4 P2 -1.9(5) . . . . ?
C1 C2 O1 P1 -5.4(5) . . . . ?
C3 C2 O1 P1 171.1(3) . . . . ?
C7 C8 O2 P1 8.6(5) . . . . ?
C9 C8 O2 P1 -169.5(3) . . . . ?
C27 C28 O3 P2 6.8(5) . . . . ?
C29 C28 O3 P2 -170.9(3) . . . . ?
C33 C34 O4 P2 -8.1(5) . . . . ?
C35 C34 O4 P2 169.1(3) . . . . ?
C13 N1 P1 O1 97.0(4) . . . . ?
P2 N1 P1 O1 -84.9(2) . . . . ?
C13 N1 P1 O2 -92.6(4) . . . . ?
P2 N1 P1 O2 85.53(19) . . . . ?
C13 N1 P1 N2 -177.9(4) . . . . ?
P2 N1 P1 N2 0.22(16) . . . . ?
C13 N1 P1 N3 2.0(4) . . . . ?
P2 N1 P1 N3 -179.85(17) . . . . ?
C2 O1 P1 N1 -95.0(3) . . . . ?
C2 O1 P1 O2 95.2(3) . . . . ?
C2 O1 P1 N2 -173.7(3) . . . . ?
C2 O1 P1 N3 5.9(3) . . . . ?
C8 O2 P1 N1 91.7(3) . . . . ?
C8 O2 P1 O1 -98.5(3) . . . . ?
C8 O2 P1 N2 170.6(3) . . . . ?
C8 O2 P1 N3 -8.9(3) . . . . ?
C20 N2 P1 N1 -172.3(4) . . . . ?
P2 N2 P1 N1 -0.23(18) . . . . ?
C20 N2 P1 O1 -54.4(4) . . . . ?
P2 N2 P1 O1 117.66(18) . . . . ?
C20 N2 P1 O2 69.4(4) . . . . ?
P2 N2 P1 O2 -118.51(18) . . . . ?
C7 N3 P1 N1 -110.8(3) . . . . ?
C1 N3 P1 N1 113.0(3) . . . . ?
C7 N3 P1 O1 131.3(3) . . . . ?
C1 N3 P1 O1 -4.9(3) . . . . ?
C7 N3 P1 O2 7.4(3) . . . . ?
C1 N3 P1 O2 -128.7(3) . . . . ?
C34 O4 P2 O3 97.8(3) . . . . ?
C34 O4 P2 N2 -92.1(3) . . . . ?
C34 O4 P2 N1 -170.8(3) . . . . ?
C34 O4 P2 N4 8.1(3) . . . . ?
C28 O3 P2 O4 -96.0(3) . . . . ?
C28 O3 P2 N2 94.2(3) . . . . ?
C28 O3 P2 N1 172.1(3) . . . . ?
C28 O3 P2 N4 -6.5(3) . . . . ?
C20 N2 P2 O4 86.2(4) . . . . ?
P1 N2 P2 O4 -85.82(19) . . . . ?
C20 N2 P2 O3 -103.3(4) . . . . ?
P1 N2 P2 O3 84.7(2) . . . . ?
C20 N2 P2 N1 172.2(4) . . . . ?
P1 N2 P2 N1 0.22(16) . . . . ?
C20 N2 P2 N4 -8.1(4) . . . . ?
P1 N2 P2 N4 179.89(16) . . . . ?
C13 N1 P2 O4 -64.6(4) . . . . ?
P1 N1 P2 O4 117.23(18) . . . . ?
C13 N1 P2 O3 58.7(4) . . . . ?
P1 N1 P2 O3 -119.45(18) . . . . ?
C13 N1 P2 N2 177.9(4) . . . . ?
P1 N1 P2 N2 -0.23(17) . . . . ?
C33 N4 P2 O4 -6.4(3) . . . . ?
C27 N4 P2 O4 128.1(3) . . . . ?
C33 N4 P2 O3 -129.7(3) . . . . ?
C27 N4 P2 O3 4.8(3) . . . . ?
C33 N4 P2 N2 111.2(3) . . . . ?
C27 N4 P2 N2 -114.4(3) . . . . ?

_refine_diff_density_max         0.620
_refine_diff_density_min         -0.315
_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_15_1821122
_database_code_depnum_ccdc_archive 'CCDC 1821122'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H50 B N2 O5 P'
_chemical_formula_weight         608.54

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'
B B 0.0013 0.0007 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   19.707(5)
_cell_length_b                   17.611(4)
_cell_length_c                   20.439(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7094(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5361
_cell_measurement_theta_min      2.517
_cell_measurement_theta_max      25.070

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             2624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44609
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.843
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6249
_reflns_number_gt                5003
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6249
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.2269
_refine_ls_wR_factor_gt          0.2029
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.32826(11) 0.96367(13) 0.36293(11) 0.0312(5) Uani 1 1 d . . . . .
C2 C 0.11851(11) 0.87544(14) 0.28912(10) 0.0327(5) Uani 1 1 d . . . . .
C3 C 0.06721(12) 0.90207(15) 0.23979(11) 0.0408(6) Uani 1 1 d . . . . .
C4 C 0.05132(17) 0.83625(19) 0.19303(15) 0.0667(9) Uani 1 1 d . . . . .
H4A H 0.017879 0.852870 0.160559 0.100 Uiso 1 1 calc R U . . .
H4B H 0.093008 0.820452 0.170707 0.100 Uiso 1 1 calc R U . . .
H4C H 0.032933 0.793396 0.217951 0.100 Uiso 1 1 calc R U . . .
C5 C 0.00309(13) 0.9284(2) 0.27377(15) 0.0647(9) Uani 1 1 d . . . . .
H5A H -0.029826 0.945561 0.241008 0.097 Uiso 1 1 calc R U . . .
H5B H -0.016301 0.886238 0.298868 0.097 Uiso 1 1 calc R U . . .
H5C H 0.013894 0.970427 0.303415 0.097 Uiso 1 1 calc R U . . .
C6 C 0.09805(15) 0.96749(18) 0.20060(14) 0.0579(8) Uani 1 1 d . . . . .
H6A H 0.065084 0.985425 0.168199 0.087 Uiso 1 1 calc R U . . .
H6B H 0.109772 1.009158 0.230295 0.087 Uiso 1 1 calc R U . . .
H6C H 0.139068 0.949795 0.178175 0.087 Uiso 1 1 calc R U . . .
C7 C 0.18759(11) 0.75928(13) 0.39899(11) 0.0344(5) Uani 1 1 d . . . . .
H7 H 0.188960 0.705678 0.393967 0.041 Uiso 1 1 calc R U . . .
C8 C 0.17299(11) 0.79297(14) 0.45460(11) 0.0355(5) Uani 1 1 d . . . . .
C9 C 0.15556(14) 0.76174(16) 0.52075(13) 0.0470(6) Uani 1 1 d . . . . .
C10 C 0.2118(2) 0.7835(2) 0.56878(15) 0.0770(11) Uani 1 1 d . . . . .
H10A H 0.201023 0.763437 0.612250 0.115 Uiso 1 1 calc R U . . .
H10B H 0.255055 0.762182 0.553809 0.115 Uiso 1 1 calc R U . . .
H10C H 0.215491 0.838980 0.571030 0.115 Uiso 1 1 calc R U . . .
C11 C 0.1503(2) 0.67520(19) 0.51656(16) 0.0712(10) Uani 1 1 d . . . . .
H11A H 0.138953 0.654630 0.559741 0.107 Uiso 1 1 calc R U . . .
H11B H 0.114847 0.661299 0.485193 0.107 Uiso 1 1 calc R U . . .
H11C H 0.193890 0.654238 0.502082 0.107 Uiso 1 1 calc R U . . .
C12 C 0.08733(18) 0.7946(2) 0.54239(17) 0.0745(10) Uani 1 1 d . . . . .
H12A H 0.075502 0.774486 0.585617 0.112 Uiso 1 1 calc R U . . .
H12B H 0.090572 0.850055 0.544634 0.112 Uiso 1 1 calc R U . . .
H12C H 0.052193 0.780275 0.510780 0.112 Uiso 1 1 calc R U . . .
C13 C 0.34214(11) 0.77674(13) 0.24628(11) 0.0344(5) Uani 1 1 d . . . . .
C14 C 0.36922(13) 0.75521(16) 0.18715(13) 0.0486(7) Uani 1 1 d . . . . .
H14 H 0.353560 0.776125 0.147053 0.058 Uiso 1 1 calc R U . . .
C15 C 0.42111(15) 0.70083(19) 0.18899(15) 0.0588(8) Uani 1 1 d . . . . .
H15 H 0.441293 0.684436 0.149218 0.071 Uiso 1 1 calc R U . . .
C16 C 0.44338(14) 0.67073(17) 0.24724(16) 0.0578(8) Uani 1 1 d . . . . .
H16 H 0.478639 0.633950 0.246902 0.069 Uiso 1 1 calc R U . . .
C17 C 0.41514(12) 0.69319(15) 0.30699(14) 0.0450(6) Uani 1 1 d . . . . .
H17 H 0.430488 0.672499 0.347277 0.054 Uiso 1 1 calc R U . . .
C18 C 0.36437(11) 0.74635(13) 0.30489(11) 0.0328(5) Uani 1 1 d . . . . .
C19 C 0.15264(11) 0.81163(13) 0.29419(11) 0.0334(5) Uani 1 1 d . . . . .
H19 H 0.145742 0.769506 0.265938 0.040 Uiso 1 1 calc R U . . .
C20 C 0.37292(12) 0.96127(14) 0.41639(12) 0.0373(6) Uani 1 1 d . . . . .
C21 C 0.42570(13) 1.01411(16) 0.41797(13) 0.0476(7) Uani 1 1 d . . . . .
H21 H 0.457853 1.012199 0.452565 0.057 Uiso 1 1 calc R U . . .
C22 C 0.43200(13) 1.06848(16) 0.37073(14) 0.0517(7) Uani 1 1 d . . . . .
H22 H 0.467529 1.104794 0.373538 0.062 Uiso 1 1 calc R U . . .
C23 C 0.38719(13) 1.07107(15) 0.31901(13) 0.0453(6) Uani 1 1 d . . . . .
H23 H 0.392516 1.108871 0.286253 0.054 Uiso 1 1 calc R U . . .
C24 C 0.33386(11) 1.01868(13) 0.31406(12) 0.0353(5) Uani 1 1 d . . . . .
C25 C 0.28553(12) 1.02387(15) 0.25668(13) 0.0422(6) Uani 1 1 d . . . . .
H25 H 0.250760 0.983037 0.262329 0.051 Uiso 1 1 calc R U . . .
C26 C 0.32121(18) 1.0097(2) 0.19130(14) 0.0677(9) Uani 1 1 d . . . . .
H26A H 0.288185 1.013577 0.155613 0.102 Uiso 1 1 calc R U . . .
H26B H 0.357003 1.047640 0.185046 0.102 Uiso 1 1 calc R U . . .
H26C H 0.341299 0.958789 0.191380 0.102 Uiso 1 1 calc R U . . .
C27 C 0.24822(16) 1.09958(17) 0.25697(19) 0.0672(9) Uani 1 1 d . . . . .
H27A H 0.217238 1.101840 0.219515 0.101 Uiso 1 1 calc R U . . .
H27B H 0.222242 1.104528 0.297631 0.101 Uiso 1 1 calc R U . . .
H27C H 0.281172 1.141114 0.253945 0.101 Uiso 1 1 calc R U . . .
C28 C 0.36577(13) 0.90426(15) 0.47208(12) 0.0436(6) Uani 1 1 d . . . . .
H28 H 0.327236 0.869503 0.461287 0.052 Uiso 1 1 calc R U . . .
C29 C 0.34824(19) 0.9458(2) 0.53554(14) 0.0663(9) Uani 1 1 d . . . . .
H29A H 0.307213 0.976359 0.528998 0.099 Uiso 1 1 calc R U . . .
H29B H 0.340279 0.908694 0.570410 0.099 Uiso 1 1 calc R U . . .
H29C H 0.385981 0.979113 0.547891 0.099 Uiso 1 1 calc R U . . .
C30 C 0.42948(16) 0.85603(18) 0.48031(15) 0.0610(8) Uani 1 1 d . . . . .
H30A H 0.422929 0.820197 0.516449 0.091 Uiso 1 1 calc R U . . .
H30B H 0.438201 0.827848 0.439831 0.091 Uiso 1 1 calc R U . . .
H30C H 0.468238 0.889048 0.489942 0.091 Uiso 1 1 calc R U . . .
C31 C 0.14084(14) 1.03282(17) 0.44073(15) 0.0550(7) Uani 1 1 d . . . . .
H31A H 0.111415 1.048670 0.403927 0.066 Uiso 1 1 calc R U . . .
H31B H 0.114853 0.996841 0.468247 0.066 Uiso 1 1 calc R U . . .
C32 C 0.1589(2) 1.0985(2) 0.4792(2) 0.0907(13) Uani 1 1 d . . . . .
H32A H 0.185692 1.133656 0.451497 0.109 Uiso 1 1 calc R U . . .
H32B H 0.188284 1.082117 0.515819 0.109 Uiso 1 1 calc R U . . .
C33 C 0.0989(3) 1.1409(3) 0.5066(2) 0.1084(16) Uani 1 1 d . . . . .
H33A H 0.115599 1.187305 0.528600 0.130 Uiso 1 1 calc R U . . .
H33B H 0.069676 1.157103 0.469738 0.130 Uiso 1 1 calc R U . . .
C34 C 0.0577(3) 1.0985(4) 0.5526(2) 0.144(3) Uani 1 1 d . . . . .
H34A H 0.020083 1.130364 0.567732 0.216 Uiso 1 1 calc R U . . .
H34B H 0.039560 1.053071 0.531093 0.216 Uiso 1 1 calc R U . . .
H34C H 0.085588 1.083343 0.590090 0.216 Uiso 1 1 calc R U . . .
B1 B 0.28034(13) 0.82969(14) 0.32737(12) 0.0303(6) Uani 1 1 d . . . . .
N1 N 0.27521(9) 0.90732(10) 0.35893(9) 0.0287(4) Uani 1 1 d . . . . .
N2 N 0.20131(9) 0.81152(10) 0.34639(9) 0.0294(4) Uani 1 1 d . . . . .
O1 O 0.17445(8) 0.87214(9) 0.45292(7) 0.0354(4) Uani 1 1 d . . . . .
O2 O 0.13471(8) 0.93033(9) 0.33599(7) 0.0335(4) Uani 1 1 d . . . . .
O4 O 0.32876(8) 0.77700(9) 0.35630(7) 0.0343(4) Uani 1 1 d . . . . .
O3 O 0.20053(8) 0.99517(9) 0.41524(8) 0.0355(4) Uani 1 1 d . . . . .
O5 O 0.29159(8) 0.82837(9) 0.25678(7) 0.0352(4) Uani 1 1 d . . . . .
P1 P 0.19768(3) 0.91208(3) 0.38488(3) 0.0276(2) 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 C24 1.396(3) . ?
C1 C20 1.404(3) . ?
C1 N1 1.444(3) . ?
C2 C19 1.314(3) . ?
C2 O2 1.398(3) . ?
C2 C3 1.503(3) . ?
C3 C5 1.515(3) . ?
C3 C6 1.529(4) . ?
C3 C4 1.535(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.314(3) . ?
C7 N2 1.441(3) . ?
C7 H7 0.9500 . ?
C8 O1 1.395(3) . ?
C8 C9 1.499(3) . ?
C9 C11 1.530(4) . ?
C9 C12 1.529(4) . ?
C9 C10 1.530(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O5 1.366(3) . ?
C13 C14 1.375(3) . ?
C13 C18 1.383(3) . ?
C14 C15 1.401(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.399(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.371(3) . ?
C17 H17 0.9500 . ?
C18 O4 1.374(3) . ?
C19 N2 1.435(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(3) . ?
C20 C28 1.524(3) . ?
C21 C22 1.366(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.402(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.514(3) . ?
C25 C27 1.523(4) . ?
C25 C26 1.530(4) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C30 1.525(4) . ?
C28 C29 1.529(4) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.443(4) . ?
C31 O3 1.447(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.507(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.450(7) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
B1 O4 1.456(3) . ?
B1 O5 1.460(3) . ?
B1 N1 1.515(3) . ?
B1 N2 1.637(3) . ?
N1 P1 1.6195(18) . ?
N2 P1 1.9392(19) . ?
O1 P1 1.6242(16) . ?
O2 P1 1.6252(16) . ?
O3 P1 1.5906(16) . ?

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
C24 C1 C20 121.9(2) . . ?
C24 C1 N1 119.6(2) . . ?
C20 C1 N1 118.5(2) . . ?
C19 C2 O2 114.86(19) . . ?
C19 C2 C3 131.6(2) . . ?
O2 C2 C3 113.4(2) . . ?
C2 C3 C5 110.4(2) . . ?
C2 C3 C6 108.6(2) . . ?
C5 C3 C6 110.0(2) . . ?
C2 C3 C4 108.6(2) . . ?
C5 C3 C4 110.3(2) . . ?
C6 C3 C4 108.9(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N2 113.5(2) . . ?
C8 C7 H7 123.3 . . ?
N2 C7 H7 123.3 . . ?
C7 C8 O1 115.2(2) . . ?
C7 C8 C9 131.6(2) . . ?
O1 C8 C9 113.2(2) . . ?
C8 C9 C11 109.3(2) . . ?
C8 C9 C12 108.9(2) . . ?
C11 C9 C12 109.5(3) . . ?
C8 C9 C10 108.7(2) . . ?
C11 C9 C10 109.5(3) . . ?
C12 C9 C10 110.9(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 C14 127.2(2) . . ?
O5 C13 C18 110.65(19) . . ?
C14 C13 C18 122.1(2) . . ?
C13 C14 C15 116.6(3) . . ?
C13 C14 H14 121.7 . . ?
C15 C14 H14 121.7 . . ?
C16 C15 C14 121.3(2) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 117.1(3) . . ?
C18 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
C17 C18 O4 128.1(2) . . ?
C17 C18 C13 121.5(2) . . ?
O4 C18 C13 110.39(19) . . ?
C2 C19 N2 113.7(2) . . ?
C2 C19 H19 123.1 . . ?
N2 C19 H19 123.1 . . ?
C21 C20 C1 117.7(2) . . ?
C21 C20 C28 119.4(2) . . ?
C1 C20 C28 122.9(2) . . ?
C22 C21 C20 121.3(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 120.9(2) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C1 C24 C23 117.7(2) . . ?
C1 C24 C25 123.1(2) . . ?
C23 C24 C25 119.2(2) . . ?
C24 C25 C27 110.7(2) . . ?
C24 C25 C26 112.2(2) . . ?
C27 C25 C26 111.6(3) . . ?
C24 C25 H25 107.4 . . ?
C27 C25 H25 107.4 . . ?
C26 C25 H25 107.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C30 C28 C20 111.9(2) . . ?
C30 C28 C29 111.1(2) . . ?
C20 C28 C29 109.8(2) . . ?
C30 C28 H28 108.0 . . ?
C20 C28 H28 108.0 . . ?
C29 C28 H28 108.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 O3 111.3(3) . . ?
C32 C31 H31A 109.4 . . ?
O3 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
O3 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C31 C32 C33 113.9(4) . . ?
C31 C32 H32A 108.8 . . ?
C33 C32 H32A 108.8 . . ?
C31 C32 H32B 108.8 . . ?
C33 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C34 C33 C32 115.2(5) . . ?
C34 C33 H33A 108.5 . . ?
C32 C33 H33A 108.5 . . ?
C34 C33 H33B 108.5 . . ?
C32 C33 H33B 108.5 . . ?
H33A C33 H33B 107.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O4 B1 O5 106.95(18) . . ?
O4 B1 N1 116.48(19) . . ?
O5 B1 N1 116.44(18) . . ?
O4 B1 N2 113.73(18) . . ?
O5 B1 N2 112.09(18) . . ?
N1 B1 N2 90.68(15) . . ?
C1 N1 B1 126.58(17) . . ?
C1 N1 P1 128.98(15) . . ?
B1 N1 P1 104.42(14) . . ?
C19 N2 C7 115.49(18) . . ?
C19 N2 B1 117.34(17) . . ?
C7 N2 B1 118.73(17) . . ?
C19 N2 P1 106.00(14) . . ?
C7 N2 P1 105.88(14) . . ?
B1 N2 P1 87.30(12) . . ?
C8 O1 P1 117.37(14) . . ?
C2 O2 P1 117.33(14) . . ?
C18 O4 B1 105.93(17) . . ?
C31 O3 P1 122.22(16) . . ?
C13 O5 B1 106.06(17) . . ?
O3 P1 N1 98.16(9) . . ?
O3 P1 O1 94.26(9) . . ?
N1 P1 O1 121.59(9) . . ?
O3 P1 O2 94.88(8) . . ?
N1 P1 O2 121.95(9) . . ?
O1 P1 O2 113.38(9) . . ?
O3 P1 N2 175.75(8) . . ?
N1 P1 N2 77.59(8) . . ?
O1 P1 N2 87.83(8) . . ?
O2 P1 N2 87.67(8) . . ?

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
C19 C2 C3 C5 126.9(3) . . . . ?
O2 C2 C3 C5 -56.5(3) . . . . ?
C19 C2 C3 C6 -112.4(3) . . . . ?
O2 C2 C3 C6 64.1(3) . . . . ?
C19 C2 C3 C4 5.9(4) . . . . ?
O2 C2 C3 C4 -177.6(2) . . . . ?
N2 C7 C8 O1 -1.0(3) . . . . ?
N2 C7 C8 C9 179.9(2) . . . . ?
C7 C8 C9 C11 -4.7(4) . . . . ?
O1 C8 C9 C11 176.1(2) . . . . ?
C7 C8 C9 C12 -124.3(3) . . . . ?
O1 C8 C9 C12 56.5(3) . . . . ?
C7 C8 C9 C10 114.8(3) . . . . ?
O1 C8 C9 C10 -64.4(3) . . . . ?
O5 C13 C14 C15 180.0(2) . . . . ?
C18 C13 C14 C15 -0.3(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 O4 179.7(2) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
O5 C13 C18 C17 -179.9(2) . . . . ?
C14 C13 C18 C17 0.4(4) . . . . ?
O5 C13 C18 O4 0.2(3) . . . . ?
C14 C13 C18 O4 -179.5(2) . . . . ?
O2 C2 C19 N2 -1.3(3) . . . . ?
C3 C2 C19 N2 175.2(2) . . . . ?
C24 C1 C20 C21 -2.8(3) . . . . ?
N1 C1 C20 C21 177.2(2) . . . . ?
C24 C1 C20 C28 176.9(2) . . . . ?
N1 C1 C20 C28 -3.1(3) . . . . ?
C1 C20 C21 C22 2.9(4) . . . . ?
C28 C20 C21 C22 -176.8(2) . . . . ?
C20 C21 C22 C23 -1.9(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C20 C1 C24 C23 1.6(3) . . . . ?
N1 C1 C24 C23 -178.4(2) . . . . ?
C20 C1 C24 C25 -178.5(2) . . . . ?
N1 C1 C24 C25 1.5(3) . . . . ?
C22 C23 C24 C1 -0.6(4) . . . . ?
C22 C23 C24 C25 179.6(2) . . . . ?
C1 C24 C25 C27 118.5(3) . . . . ?
C23 C24 C25 C27 -61.7(3) . . . . ?
C1 C24 C25 C26 -116.1(3) . . . . ?
C23 C24 C25 C26 63.7(3) . . . . ?
C21 C20 C28 C30 -58.0(3) . . . . ?
C1 C20 C28 C30 122.3(3) . . . . ?
C21 C20 C28 C29 65.8(3) . . . . ?
C1 C20 C28 C29 -113.9(3) . . . . ?
O3 C31 C32 C33 179.4(4) . . . . ?
C31 C32 C33 C34 63.3(6) . . . . ?
C24 C1 N1 B1 91.8(3) . . . . ?
C20 C1 N1 B1 -88.2(3) . . . . ?
C24 C1 N1 P1 -86.8(3) . . . . ?
C20 C1 N1 P1 93.2(2) . . . . ?
O4 B1 N1 C1 63.1(3) . . . . ?
O5 B1 N1 C1 -64.6(3) . . . . ?
N2 B1 N1 C1 -179.81(19) . . . . ?
O4 B1 N1 P1 -118.01(18) . . . . ?
O5 B1 N1 P1 114.29(18) . . . . ?
N2 B1 N1 P1 -0.91(15) . . . . ?
C2 C19 N2 C7 114.0(2) . . . . ?
C2 C19 N2 B1 -98.2(2) . . . . ?
C2 C19 N2 P1 -2.9(2) . . . . ?
C8 C7 N2 C19 -113.1(2) . . . . ?
C8 C7 N2 B1 99.6(2) . . . . ?
C8 C7 N2 P1 3.8(2) . . . . ?
O4 B1 N2 C19 -133.1(2) . . . . ?
O5 B1 N2 C19 -11.7(3) . . . . ?
N1 B1 N2 C19 107.37(19) . . . . ?
O4 B1 N2 C7 13.6(3) . . . . ?
O5 B1 N2 C7 135.1(2) . . . . ?
N1 B1 N2 C7 -105.9(2) . . . . ?
O4 B1 N2 P1 120.23(17) . . . . ?
O5 B1 N2 P1 -118.30(17) . . . . ?
N1 B1 N2 P1 0.74(12) . . . . ?
C7 C8 O1 P1 -3.3(3) . . . . ?
C9 C8 O1 P1 176.05(16) . . . . ?
C19 C2 O2 P1 6.1(2) . . . . ?
C3 C2 O2 P1 -171.06(15) . . . . ?
C17 C18 O4 B1 -179.3(2) . . . . ?
C13 C18 O4 B1 0.7(2) . . . . ?
O5 B1 O4 C18 -1.2(2) . . . . ?
N1 B1 O4 C18 -133.44(19) . . . . ?
N2 B1 O4 C18 123.07(19) . . . . ?
C32 C31 O3 P1 166.2(3) . . . . ?
C14 C13 O5 B1 178.8(2) . . . . ?
C18 C13 O5 B1 -1.0(2) . . . . ?
O4 B1 O5 C13 1.3(2) . . . . ?
N1 B1 O5 C13 133.6(2) . . . . ?
N2 B1 O5 C13 -123.94(19) . . . . ?
C31 O3 P1 N1 173.9(2) . . . . ?
C31 O3 P1 O1 -63.3(2) . . . . ?
C31 O3 P1 O2 50.6(2) . . . . ?
C1 N1 P1 O3 -0.6(2) . . . . ?
B1 N1 P1 O3 -179.47(14) . . . . ?
C1 N1 P1 O1 -100.8(2) . . . . ?
B1 N1 P1 O1 80.37(16) . . . . ?
C1 N1 P1 O2 100.4(2) . . . . ?
B1 N1 P1 O2 -78.47(16) . . . . ?
C1 N1 P1 N2 179.6(2) . . . . ?
B1 N1 P1 N2 0.79(13) . . . . ?
C8 O1 P1 O3 -171.79(16) . . . . ?
C8 O1 P1 N1 -69.49(18) . . . . ?
C8 O1 P1 O2 91.02(17) . . . . ?
C8 O1 P1 N2 4.50(16) . . . . ?
C2 O2 P1 O3 170.35(15) . . . . ?
C2 O2 P1 N1 67.57(18) . . . . ?
C2 O2 P1 O1 -92.87(15) . . . . ?
C2 O2 P1 N2 -6.24(15) . . . . ?

_refine_diff_density_max         0.878
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.051



