# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1849849'
_audit_update_record             
;
2018-11-08 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H41 N2 P'
_chemical_formula_weight         484.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   8.277(5)
_cell_length_b                   43.32(3)
_cell_length_c                   8.716(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.867(8)
_cell_angle_gamma                90
_cell_volume                     2880(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1675
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      20.70

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5479
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14188
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -57
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.880
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.899
_reflns_number_total             6151
_reflns_number_gt                3587
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.726
_reflns_Friedel_fraction_full    0.798

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.27(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6151
_refine_ls_number_parameters     330
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1696
_refine_ls_wR_factor_gt          0.1433
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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 0.6829(6) 0.62487(10) 0.5117(5) 0.0379(10) Uani 1 1 d . . . . .
C2 C 0.7252(6) 0.59932(10) 0.4334(6) 0.0404(11) Uani 1 1 d . . . . .
C3 C 0.8904(7) 0.59767(12) 0.4294(6) 0.0473(12) Uani 1 1 d . . . . .
H4 H 0.918997 0.580602 0.376301 0.057 Uiso 1 1 calc R U . . .
C4 C 1.0174(6) 0.62075(12) 0.5024(7) 0.0518(13) Uani 1 1 d . . . . .
H5 H 1.129837 0.618908 0.497883 0.062 Uiso 1 1 calc R U . . .
C5 C 0.9813(7) 0.64554(12) 0.5788(6) 0.0497(13) Uani 1 1 d . . . . .
H6 H 1.068350 0.660827 0.628615 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8126(6) 0.64847(10) 0.5839(6) 0.0376(10) Uani 1 1 d . . . . .
C7 C 0.7518(6) 0.67267(11) 0.6542(6) 0.0444(12) Uani 1 1 d . . . . .
H7A H 0.819608 0.690185 0.707242 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5959(6) 0.57395(11) 0.3580(7) 0.0475(12) Uani 1 1 d . . . . .
H8A H 0.596412 0.568352 0.248081 0.057 Uiso 1 1 calc R U . . .
H8B H 0.630350 0.555482 0.430405 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2874(6) 0.56146(10) 0.3216(6) 0.0398(11) Uani 1 1 d . . . . .
C10 C 0.3007(6) 0.54235(11) 0.4568(6) 0.0469(12) Uani 1 1 d . . . . .
C11 C 0.1685(7) 0.52118(12) 0.4351(8) 0.0582(14) Uani 1 1 d . . . . .
H11 H 0.178544 0.507523 0.523601 0.070 Uiso 1 1 calc R U . . .
C12 C 0.0241(7) 0.51941(11) 0.2899(8) 0.0575(14) Uani 1 1 d . . . . .
H12 H -0.064594 0.504625 0.278600 0.069 Uiso 1 1 calc R U . . .
C13 C 0.0063(7) 0.53883(12) 0.1604(7) 0.0516(13) Uani 1 1 d . . . . .
H13 H -0.096459 0.537688 0.061175 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1356(6) 0.56018(10) 0.1713(6) 0.0439(11) Uani 1 1 d . . . . .
C15 C 0.4514(7) 0.54471(13) 0.6271(7) 0.0562(14) Uani 1 1 d . . . . .
H15 H 0.531570 0.561466 0.620480 0.067 Uiso 1 1 calc R U . . .
C16 C 0.5575(9) 0.51500(15) 0.6738(9) 0.0807(19) Uani 1 1 d . . . . .
H16A H 0.604076 0.510190 0.588939 0.121 Uiso 1 1 calc R U . . .
H16B H 0.481972 0.498081 0.680530 0.121 Uiso 1 1 calc R U . . .
H16C H 0.654832 0.517604 0.781969 0.121 Uiso 1 1 calc R U . . .
C17 C 0.3858(11) 0.55369(18) 0.7630(8) 0.085(2) Uani 1 1 d . . . . .
H17A H 0.313877 0.536940 0.778328 0.127 Uiso 1 1 calc R U . . .
H17B H 0.315198 0.572545 0.729904 0.127 Uiso 1 1 calc R U . . .
H17C H 0.486300 0.557341 0.867781 0.127 Uiso 1 1 calc R U . . .
C18 C 0.1108(7) 0.58263(11) 0.0297(6) 0.0490(12) Uani 1 1 d . . . . .
H18 H 0.227448 0.585666 0.022522 0.059 Uiso 1 1 calc R U . . .
C19 C -0.0171(9) 0.57122(16) -0.1397(7) 0.0775(19) Uani 1 1 d . . . . .
H19A H -0.014626 0.585270 -0.226898 0.116 Uiso 1 1 calc R U . . .
H19B H -0.135802 0.570592 -0.140670 0.116 Uiso 1 1 calc R U . . .
H19C H 0.017142 0.550461 -0.160327 0.116 Uiso 1 1 calc R U . . .
C20 C 0.0483(9) 0.61415(13) 0.0656(8) 0.0671(17) Uani 1 1 d . . . . .
H20A H -0.068686 0.612004 0.067632 0.101 Uiso 1 1 calc R U . . .
H20B H 0.043509 0.628803 -0.021740 0.101 Uiso 1 1 calc R U . . .
H20C H 0.130228 0.621753 0.173739 0.101 Uiso 1 1 calc R U . . .
C21 C 0.4892(6) 0.68968(11) 0.6968(6) 0.0440(11) Uani 1 1 d . . . . .
C22 C 0.4984(7) 0.68676(12) 0.8615(7) 0.0494(12) Uani 1 1 d . . . . .
C23 C 0.4078(8) 0.70822(14) 0.9146(8) 0.0656(16) Uani 1 1 d . . . . .
H23 H 0.414232 0.707115 1.025650 0.079 Uiso 1 1 calc R U . . .
C24 C 0.3091(8) 0.73103(15) 0.8119(8) 0.0700(17) Uani 1 1 d . . . . .
H24 H 0.249328 0.745533 0.852663 0.084 Uiso 1 1 calc R U . . .
C25 C 0.2960(8) 0.73303(13) 0.6497(8) 0.0645(16) Uani 1 1 d . . . . .
H25 H 0.224985 0.748616 0.578628 0.077 Uiso 1 1 calc R U . . .
C26 C 0.3861(6) 0.71241(11) 0.5890(7) 0.0475(12) Uani 1 1 d . . . . .
C27 C 0.6026(7) 0.66129(13) 0.9763(7) 0.0583(14) Uani 1 1 d . . . . .
H27 H 0.671546 0.650505 0.920151 0.070 Uiso 1 1 calc R U . . .
C28 C 0.4803(11) 0.63740(17) 1.0055(9) 0.086(2) Uani 1 1 d . . . . .
H28A H 0.412880 0.647268 1.062834 0.129 Uiso 1 1 calc R U . . .
H28B H 0.550268 0.620496 1.074116 0.129 Uiso 1 1 calc R U . . .
H28C H 0.399745 0.629215 0.898213 0.129 Uiso 1 1 calc R U . . .
C29 C 0.7305(10) 0.67325(17) 1.1411(9) 0.096(2) Uani 1 1 d . . . . .
H29A H 0.666281 0.683918 1.199082 0.144 Uiso 1 1 calc R U . . .
H29B H 0.812051 0.687676 1.122135 0.144 Uiso 1 1 calc R U . . .
H29C H 0.796225 0.655931 1.209166 0.144 Uiso 1 1 calc R U . . .
C30 C 0.3667(8) 0.71431(13) 0.4078(7) 0.0563(14) Uani 1 1 d . . . . .
H30 H 0.463586 0.702044 0.395994 0.068 Uiso 1 1 calc R U . . .
C31 C 0.1926(9) 0.70013(16) 0.2938(8) 0.0785(19) Uani 1 1 d . . . . .
H31A H 0.096084 0.710690 0.310618 0.118 Uiso 1 1 calc R U . . .
H31B H 0.191127 0.678163 0.320015 0.118 Uiso 1 1 calc R U . . .
H31C H 0.178857 0.702438 0.177507 0.118 Uiso 1 1 calc R U . . .
C32 C 0.3797(11) 0.74764(16) 0.3532(9) 0.083(2) Uani 1 1 d . . . . .
H32A H 0.487677 0.757138 0.431693 0.124 Uiso 1 1 calc R U . . .
H32B H 0.278292 0.759488 0.351718 0.124 Uiso 1 1 calc R U . . .
H32C H 0.381610 0.747537 0.241490 0.124 Uiso 1 1 calc R U . . .
N1 N 0.4199(5) 0.58356(9) 0.3380(6) 0.0465(10) Uani 1 1 d D . . . .
N2 N 0.5821(5) 0.66776(8) 0.6365(5) 0.0419(9) Uani 1 1 d . . . . .
P1 P 0.48827(17) 0.63395(3) 0.53590(18) 0.0531(4) Uani 1 1 d . . . . .
H1A H 0.383(7) 0.5990(10) 0.264(5) 0.060(17) Uiso 1 1 d 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 1.414(6) . ?
C1 C6 1.438(6) . ?
C1 P1 1.749(5) . ?
C2 C3 1.383(7) . ?
C2 C8 1.496(7) . ?
C3 C4 1.410(7) . ?
C3 H4 0.9500 . ?
C4 C5 1.357(7) . ?
C4 H5 0.9500 . ?
C5 C6 1.420(7) . ?
C5 H6 0.9500 . ?
C6 C7 1.403(7) . ?
C7 N2 1.369(6) . ?
C7 H7A 0.9500 . ?
C8 N1 1.459(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.409(7) . ?
C9 N1 1.420(6) . ?
C9 C14 1.421(7) . ?
C10 C11 1.383(7) . ?
C10 C15 1.526(7) . ?
C11 C12 1.364(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.369(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(7) . ?
C13 H13 0.9500 . ?
C14 C18 1.522(7) . ?
C15 C16 1.522(8) . ?
C15 C17 1.533(8) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.526(8) . ?
C18 C20 1.535(7) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.399(7) . ?
C21 C22 1.413(7) . ?
C21 N2 1.444(6) . ?
C22 C23 1.382(8) . ?
C22 C27 1.514(7) . ?
C23 C24 1.370(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(7) . ?
C25 H25 0.9500 . ?
C26 C30 1.526(8) . ?
C27 C29 1.507(9) . ?
C27 C28 1.537(9) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.525(9) . ?
C30 C32 1.537(8) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
N1 H1A 0.90(3) . ?
N2 P1 1.729(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.0(4) . . ?
C2 C1 P1 130.3(3) . . ?
C6 C1 P1 110.7(3) . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 C8 119.8(4) . . ?
C1 C2 C8 121.2(4) . . ?
C2 C3 C4 121.5(5) . . ?
C2 C3 H4 119.2 . . ?
C4 C3 H4 119.2 . . ?
C5 C4 C3 121.0(5) . . ?
C5 C4 H5 119.5 . . ?
C3 C4 H5 119.5 . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 H6 120.2 . . ?
C6 C5 H6 120.2 . . ?
C7 C6 C5 127.2(4) . . ?
C7 C6 C1 112.9(4) . . ?
C5 C6 C1 119.9(4) . . ?
N2 C7 C6 111.2(4) . . ?
N2 C7 H7A 124.4 . . ?
C6 C7 H7A 124.4 . . ?
N1 C8 C2 110.7(4) . . ?
N1 C8 H8A 109.5 . . ?
C2 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 N1 120.4(4) . . ?
C10 C9 C14 120.1(4) . . ?
N1 C9 C14 119.4(4) . . ?
C11 C10 C9 118.3(5) . . ?
C11 C10 C15 118.8(5) . . ?
C9 C10 C15 122.9(4) . . ?
C12 C11 C10 121.7(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 120.3(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 121.3(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C9 118.1(4) . . ?
C13 C14 C18 120.8(4) . . ?
C9 C14 C18 121.0(4) . . ?
C16 C15 C10 111.9(5) . . ?
C16 C15 C17 110.4(5) . . ?
C10 C15 C17 111.6(5) . . ?
C16 C15 H15 107.6 . . ?
C10 C15 H15 107.6 . . ?
C17 C15 H15 107.6 . . ?
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 . . ?
C14 C18 C19 113.7(4) . . ?
C14 C18 C20 110.7(4) . . ?
C19 C18 C20 108.9(5) . . ?
C14 C18 H18 107.8 . . ?
C19 C18 H18 107.8 . . ?
C20 C18 H18 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 121.6(5) . . ?
C26 C21 N2 119.4(4) . . ?
C22 C21 N2 119.0(4) . . ?
C23 C22 C21 117.2(5) . . ?
C23 C22 C27 120.8(5) . . ?
C21 C22 C27 121.9(5) . . ?
C24 C23 C22 122.0(6) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 120.3(6) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 120.6(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 118.2(5) . . ?
C25 C26 C30 120.1(5) . . ?
C21 C26 C30 121.6(5) . . ?
C29 C27 C22 112.9(5) . . ?
C29 C27 C28 109.7(5) . . ?
C22 C27 C28 110.9(5) . . ?
C29 C27 H27 107.7 . . ?
C22 C27 H27 107.7 . . ?
C28 C27 H27 107.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C26 110.2(5) . . ?
C31 C30 C32 109.8(5) . . ?
C26 C30 C32 112.3(5) . . ?
C31 C30 H30 108.2 . . ?
C26 C30 H30 108.2 . . ?
C32 C30 H30 108.2 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C9 N1 C8 121.1(4) . . ?
C9 N1 H1A 113(4) . . ?
C8 N1 H1A 110(4) . . ?
C7 N2 C21 121.7(4) . . ?
C7 N2 P1 115.3(3) . . ?
C21 N2 P1 123.0(3) . . ?
N2 P1 C1 89.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(6) . . . . ?
P1 C1 C2 C3 179.3(4) . . . . ?
C6 C1 C2 C8 179.3(4) . . . . ?
P1 C1 C2 C8 -1.8(7) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C8 C2 C3 C4 -178.6(5) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C4 C5 C6 C7 -178.7(5) . . . . ?
C4 C5 C6 C1 1.5(7) . . . . ?
C2 C1 C6 C7 178.8(4) . . . . ?
P1 C1 C6 C7 -0.3(5) . . . . ?
C2 C1 C6 C5 -1.3(6) . . . . ?
P1 C1 C6 C5 179.6(4) . . . . ?
C5 C6 C7 N2 -179.9(4) . . . . ?
C1 C6 C7 N2 0.0(5) . . . . ?
C3 C2 C8 N1 -165.8(5) . . . . ?
C1 C2 C8 N1 15.3(6) . . . . ?
N1 C9 C10 C11 180.0(4) . . . . ?
C14 C9 C10 C11 4.1(7) . . . . ?
N1 C9 C10 C15 1.9(7) . . . . ?
C14 C9 C10 C15 -173.9(4) . . . . ?
C9 C10 C11 C12 -2.8(8) . . . . ?
C15 C10 C11 C12 175.3(5) . . . . ?
C10 C11 C12 C13 0.0(9) . . . . ?
C11 C12 C13 C14 1.7(9) . . . . ?
C12 C13 C14 C9 -0.3(7) . . . . ?
C12 C13 C14 C18 -177.2(5) . . . . ?
C10 C9 C14 C13 -2.6(7) . . . . ?
N1 C9 C14 C13 -178.5(4) . . . . ?
C10 C9 C14 C18 174.3(4) . . . . ?
N1 C9 C14 C18 -1.6(7) . . . . ?
C11 C10 C15 C16 63.8(7) . . . . ?
C9 C10 C15 C16 -118.2(6) . . . . ?
C11 C10 C15 C17 -60.5(7) . . . . ?
C9 C10 C15 C17 117.6(6) . . . . ?
C13 C14 C18 C19 -24.8(7) . . . . ?
C9 C14 C18 C19 158.4(5) . . . . ?
C13 C14 C18 C20 98.1(6) . . . . ?
C9 C14 C18 C20 -78.7(6) . . . . ?
C26 C21 C22 C23 -3.0(8) . . . . ?
N2 C21 C22 C23 179.9(5) . . . . ?
C26 C21 C22 C27 177.0(5) . . . . ?
N2 C21 C22 C27 -0.1(7) . . . . ?
C21 C22 C23 C24 1.6(9) . . . . ?
C27 C22 C23 C24 -178.4(5) . . . . ?
C22 C23 C24 C25 0.6(10) . . . . ?
C23 C24 C25 C26 -1.5(10) . . . . ?
C24 C25 C26 C21 0.2(9) . . . . ?
C24 C25 C26 C30 178.3(6) . . . . ?
C22 C21 C26 C25 2.1(7) . . . . ?
N2 C21 C26 C25 179.2(5) . . . . ?
C22 C21 C26 C30 -176.0(5) . . . . ?
N2 C21 C26 C30 1.1(7) . . . . ?
C23 C22 C27 C29 -52.8(7) . . . . ?
C21 C22 C27 C29 127.2(6) . . . . ?
C23 C22 C27 C28 70.8(7) . . . . ?
C21 C22 C27 C28 -109.2(6) . . . . ?
C25 C26 C30 C31 -77.4(6) . . . . ?
C21 C26 C30 C31 100.7(6) . . . . ?
C25 C26 C30 C32 45.3(7) . . . . ?
C21 C26 C30 C32 -136.6(6) . . . . ?
C10 C9 N1 C8 67.9(7) . . . . ?
C14 C9 N1 C8 -116.3(5) . . . . ?
C2 C8 N1 C9 -159.2(4) . . . . ?
C6 C7 N2 C21 -179.1(4) . . . . ?
C6 C7 N2 P1 0.3(5) . . . . ?
C26 C21 N2 C7 93.1(6) . . . . ?
C22 C21 N2 C7 -89.8(6) . . . . ?
C26 C21 N2 P1 -86.2(5) . . . . ?
C22 C21 N2 P1 91.0(5) . . . . ?
C7 N2 P1 C1 -0.4(3) . . . . ?
C21 N2 P1 C1 179.0(4) . . . . ?
C2 C1 P1 N2 -178.6(4) . . . . ?
C6 C1 P1 N2 0.3(3) . . . . ?

_refine_diff_density_max         0.715
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.044












# start Validation Reply Form

_vrf_PLAT094_shelx               
;
PROBLEM: Ratio of Maximum / Minimum Residual Density .... 2.72 Report
RESPONSE: The highest peak is 0.71 eA-3 at 1.02 A from P1.
Probably, there is a minor (0.9:0.1) disorder of the molecule;
in that case the highest residual density peak corresponds to
the second position of the P atom.
;

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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1849852'
_audit_update_record             
;
2018-06-16 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H39 N2 P'
_chemical_formula_weight         482.62

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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   21.2829(7)
_cell_length_b                   8.2036(3)
_cell_length_c                   16.1186(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2814.25(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4055
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.73

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.138
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7171
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30233
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.914
_diffrn_reflns_theta_max         27.914
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3370
_reflns_number_gt                2163
_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       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0553P)²+0.7902P] 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         3370
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
P P 0.52095(4) 0.38449(10) 0.73533(5) 0.0323(2) Uani 0.5 1 d . . P . .
N1 N 0.59321(6) 0.42270(18) 0.69665(8) 0.0355(3) Uani 1 1 d . . . . .
C1 C 0.500000 0.5926(3) 0.750000 0.0405(6) Uani 1 2 d S T P . .
C2 C 0.55273(8) 0.6795(2) 0.71909(11) 0.0422(4) Uani 1 1 d . . . . .
C3 C 0.55169(9) 0.8489(2) 0.71946(13) 0.0519(5) Uani 1 1 d . . . . .
H3A H 0.586634 0.908156 0.698632 0.062 Uiso 1 1 calc R U . . .
C4 C 0.500000 0.9314(3) 0.750000 0.0541(8) Uani 1 2 d S T P . .
H4A H 0.500000 1.047170 0.750001 0.065 Uiso 1 2 calc R U P . .
C5 C 0.60237(8) 0.5796(2) 0.68904(11) 0.0447(4) Uani 1 1 d . . . . .
H5A H 0.639483 0.623680 0.665173 0.054 Uiso 1 1 calc R U . . .
C6 C 0.63474(7) 0.3032(2) 0.66275(10) 0.0334(4) Uani 1 1 d . . . . .
C7 C 0.67803(7) 0.2250(2) 0.71492(10) 0.0359(4) Uani 1 1 d . . . . .
C8 C 0.71526(8) 0.1034(2) 0.68084(12) 0.0467(5) Uani 1 1 d . . . . .
H8A H 0.745440 0.050008 0.714735 0.056 Uiso 1 1 calc R U . . .
C9 C 0.70934(9) 0.0582(3) 0.59858(13) 0.0537(5) Uani 1 1 d . . . . .
H9A H 0.735152 -0.025587 0.576366 0.064 Uiso 1 1 calc R U . . .
C10 C 0.66585(9) 0.1352(2) 0.54903(12) 0.0494(5) Uani 1 1 d . . . . .
H10A H 0.662014 0.103077 0.492636 0.059 Uiso 1 1 calc R U . . .
C11 C 0.62739(8) 0.2587(2) 0.57911(10) 0.0390(4) Uani 1 1 d . . . . .
C12 C 0.57869(8) 0.3385(3) 0.52387(11) 0.0464(5) Uani 1 1 d . . . . .
H12A H 0.556157 0.422092 0.557851 0.056 Uiso 1 1 calc R U . . .
C13 C 0.53008(11) 0.2147(4) 0.49421(19) 0.0923(9) Uani 1 1 d . . . . .
H13A H 0.511514 0.159521 0.542236 0.138 Uiso 1 1 calc R U . . .
H13B H 0.497027 0.271057 0.463059 0.138 Uiso 1 1 calc R U . . .
H13C H 0.550476 0.134164 0.458306 0.138 Uiso 1 1 calc R U . . .
C14 C 0.60776(12) 0.4247(4) 0.45113(17) 0.0999(11) Uani 1 1 d . . . . .
H14A H 0.574623 0.474226 0.417285 0.150 Uiso 1 1 calc R U . . .
H14B H 0.636281 0.509798 0.471153 0.150 Uiso 1 1 calc R U . . .
H14C H 0.631339 0.346145 0.417511 0.150 Uiso 1 1 calc R U . . .
C15 C 0.68204(8) 0.2668(2) 0.80658(11) 0.0422(4) Uani 1 1 d . . . . .
H15A H 0.669308 0.383376 0.813214 0.051 Uiso 1 1 calc R U . . .
C16 C 0.63574(9) 0.1627(3) 0.85590(11) 0.0545(5) Uani 1 1 d . . . . .
H16A H 0.638696 0.190496 0.914897 0.082 Uiso 1 1 calc R U . . .
H16B H 0.592929 0.183583 0.836200 0.082 Uiso 1 1 calc R U . . .
H16C H 0.645876 0.047108 0.848250 0.082 Uiso 1 1 calc R U . . .
C17 C 0.74779(10) 0.2481(3) 0.84263(15) 0.0658(6) Uani 1 1 d . . . . .
H17A H 0.747135 0.276769 0.901647 0.099 Uiso 1 1 calc R U . . .
H17B H 0.761729 0.134967 0.836244 0.099 Uiso 1 1 calc R U . . .
H17C H 0.776802 0.320639 0.813191 0.099 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P P 1.0094(15) 3_656 ?
P N1 1.6888(15) . ?
P C1 1.780(2) . ?
N1 C5 1.308(2) . ?
N1 C6 1.429(2) . ?
C1 C2 1.420(2) 3_656 ?
C1 C2 1.420(2) . ?
C2 C3 1.389(3) . ?
C2 C5 1.422(2) . ?
C3 C4 1.382(2) . ?
C3 H3A 0.9500 . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C6 C7 1.402(2) . ?
C6 C11 1.405(2) . ?
C7 C8 1.388(2) . ?
C7 C15 1.519(2) . ?
C8 C9 1.383(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.376(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.515(2) . ?
C12 C14 1.502(3) . ?
C12 C13 1.527(3) . ?
C12 H12A 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.523(3) . ?
C15 C16 1.527(3) . ?
C15 H15A 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P P N1 167.82(8) 3_656 . ?
P P C1 73.53(3) 3_656 . ?
N1 P C1 95.69(7) . . ?
C5 N1 C6 123.19(15) . . ?
C5 N1 P 110.68(13) . . ?
C6 N1 P 125.26(12) . . ?
C2 C1 C2 119.7(2) 3_656 . ?
C2 C1 P 136.57(13) 3_656 . ?
C2 C1 P 103.71(10) . . ?
C2 C1 P 103.71(10) 3_656 3_656 ?
C2 C1 P 136.57(13) . 3_656 ?
P C1 P 32.94(7) . 3_656 ?
C3 C2 C1 119.21(18) . . ?
C3 C2 C5 126.11(19) . . ?
C1 C2 C5 114.67(17) . . ?
C4 C3 C2 120.25(19) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C3 121.4(3) . 3_656 ?
C3 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 3_656 . ?
N1 C5 C2 115.12(17) . . ?
N1 C5 H5A 122.4 . . ?
C2 C5 H5A 122.4 . . ?
C7 C6 C11 121.99(15) . . ?
C7 C6 N1 119.40(14) . . ?
C11 C6 N1 118.42(14) . . ?
C8 C7 C6 117.81(15) . . ?
C8 C7 C15 120.99(15) . . ?
C6 C7 C15 121.14(15) . . ?
C9 C8 C7 121.35(17) . . ?
C9 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
C10 C9 C8 119.66(18) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
C9 C10 C11 121.90(17) . . ?
C9 C10 H10A 119.0 . . ?
C11 C10 H10A 119.0 . . ?
C10 C11 C6 117.27(16) . . ?
C10 C11 C12 120.86(16) . . ?
C6 C11 C12 121.86(16) . . ?
C14 C12 C11 112.35(15) . . ?
C14 C12 C13 110.3(2) . . ?
C11 C12 C13 111.12(18) . . ?
C14 C12 H12A 107.6 . . ?
C11 C12 H12A 107.6 . . ?
C13 C12 H12A 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 C17 113.59(16) . . ?
C7 C15 C16 110.11(15) . . ?
C17 C15 C16 109.76(16) . . ?
C7 C15 H15A 107.7 . . ?
C17 C15 H15A 107.7 . . ?
C16 C15 H15A 107.7 . . ?
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 . . ?

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
P P N1 C5 -30.9(6) 3_656 . . . ?
C1 P N1 C5 -3.56(13) . . . . ?
P P N1 C6 159.6(5) 3_656 . . . ?
C1 P N1 C6 -173.08(12) . . . . ?
P P C1 C2 -5.03(15) 3_656 . . 3_656 ?
N1 P C1 C2 -179.24(11) . . . 3_656 ?
P P C1 C2 176.44(11) 3_656 . . . ?
N1 P C1 C2 2.23(9) . . . . ?
N1 P C1 P -174.20(13) . . . 3_656 ?
C2 C1 C2 C3 -0.17(12) 3_656 . . . ?
P C1 C2 C3 178.66(14) . . . . ?
P C1 C2 C3 -178.52(11) 3_656 . . . ?
C2 C1 C2 C5 -179.38(16) 3_656 . . . ?
P C1 C2 C5 -0.54(14) . . . . ?
P C1 C2 C5 2.28(19) 3_656 . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C5 C2 C3 C4 179.45(14) . . . . ?
C2 C3 C4 C3 -0.18(13) . . . 3_656 ?
C6 N1 C5 C2 173.59(14) . . . . ?
P N1 C5 C2 3.81(19) . . . . ?
C3 C2 C5 N1 178.74(17) . . . . ?
C1 C2 C5 N1 -2.1(2) . . . . ?
C5 N1 C6 C7 101.04(19) . . . . ?
P N1 C6 C7 -90.70(17) . . . . ?
C5 N1 C6 C11 -83.9(2) . . . . ?
P N1 C6 C11 84.39(18) . . . . ?
C11 C6 C7 C8 1.7(2) . . . . ?
N1 C6 C7 C8 176.56(15) . . . . ?
C11 C6 C7 C15 -175.67(15) . . . . ?
N1 C6 C7 C15 -0.8(2) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C15 C7 C8 C9 176.23(18) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C6 0.3(3) . . . . ?
C9 C10 C11 C12 -178.36(18) . . . . ?
C7 C6 C11 C10 -1.3(2) . . . . ?
N1 C6 C11 C10 -176.21(15) . . . . ?
C7 C6 C11 C12 177.38(15) . . . . ?
N1 C6 C11 C12 2.4(2) . . . . ?
C10 C11 C12 C14 -62.5(3) . . . . ?
C6 C11 C12 C14 118.9(2) . . . . ?
C10 C11 C12 C13 61.7(2) . . . . ?
C6 C11 C12 C13 -116.9(2) . . . . ?
C8 C7 C15 C17 33.9(2) . . . . ?
C6 C7 C15 C17 -148.86(17) . . . . ?
C8 C7 C15 C16 -89.7(2) . . . . ?
C6 C7 C15 C16 87.6(2) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040









# start Validation Reply Form

_vrf_PLAT230_shelx               
;
PROBLEM: Hirshfeld Test Diff for   N1       --C5        .        9.6 s.u.  
RESPONSE: The atom types for N1 and C5 are correct.
;

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

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1849850'
_audit_update_record             
;
2018-06-16 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H41 N2 O2 P'
_chemical_formula_weight         528.65

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                   10.6711(6)
_cell_length_b                   20.7210(12)
_cell_length_c                   13.5816(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.933(3)
_cell_angle_gamma                90
_cell_volume                     3001.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8400
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.99
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5529
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32015
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.793
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8168
_reflns_number_gt                5254
_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       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0868P)²+1.1031P] 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         8168
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1816
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.57346(5) 0.35647(2) 0.63539(3) 0.03084(14) Uani 1 1 d . . . . .
N1 N 0.58878(16) 0.41928(8) 0.71119(11) 0.0313(4) Uani 1 1 d . . . . .
N2 N 0.64064(17) 0.25625(8) 0.49938(12) 0.0333(4) Uani 1 1 d . . . . .
O1 O 0.49214(14) 0.38822(7) 0.53413(10) 0.0399(4) Uani 1 1 d . . . . .
O2 O 0.3269(2) 0.37589(13) 0.43266(15) 0.0868(7) Uani 1 1 d . . . . .
C1 C 0.72815(18) 0.37346(9) 0.58980(13) 0.0297(4) Uani 1 1 d . . . . .
C2 C 0.79833(19) 0.33644(9) 0.52462(13) 0.0315(4) Uani 1 1 d . . . . .
C3 C 0.9166(2) 0.35854(10) 0.50050(15) 0.0374(5) Uani 1 1 d . . . . .
H3A H 0.965357 0.333962 0.456856 0.045 Uiso 1 1 calc R U . . .
C4 C 0.9643(2) 0.41549(11) 0.53880(15) 0.0383(5) Uani 1 1 d . . . . .
H4A H 1.045066 0.429725 0.521068 0.046 Uiso 1 1 calc R U . . .
C5 C 0.8954(2) 0.45195(10) 0.60275(14) 0.0370(5) Uani 1 1 d . . . . .
H5A H 0.928146 0.491253 0.628806 0.044 Uiso 1 1 calc R U . . .
C6 C 0.77731(19) 0.43044(9) 0.62856(13) 0.0314(4) Uani 1 1 d . . . . .
C7 C 0.6934(2) 0.46374(10) 0.69868(14) 0.0354(5) Uani 1 1 d . . . . .
H7A H 0.738164 0.471933 0.762478 0.043 Uiso 1 1 calc R U . . .
H7B H 0.663291 0.505386 0.671079 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7514(2) 0.27506(10) 0.48528(14) 0.0345(4) Uani 1 1 d . . . . .
H8A H 0.805324 0.248668 0.448260 0.041 Uiso 1 1 calc R U . . .
C9 C 0.50854(19) 0.42885(9) 0.79317(13) 0.0328(4) Uani 1 1 d . . . . .
C10 C 0.4084(2) 0.47180(10) 0.78391(15) 0.0371(5) Uani 1 1 d . . . . .
C11 C 0.3325(2) 0.47942(13) 0.86467(17) 0.0502(6) Uani 1 1 d . . . . .
H11A H 0.263571 0.508414 0.860299 0.060 Uiso 1 1 calc R U . . .
C12 C 0.3556(3) 0.44587(14) 0.95012(18) 0.0588(7) Uani 1 1 d . . . . .
H12A H 0.302458 0.451586 1.004147 0.071 Uiso 1 1 calc R U . . .
C13 C 0.4552(2) 0.40398(13) 0.95837(17) 0.0522(6) Uani 1 1 d . . . . .
H13A H 0.469861 0.381018 1.018191 0.063 Uiso 1 1 calc R U . . .
C14 C 0.5349(2) 0.39458(11) 0.88060(14) 0.0378(5) Uani 1 1 d . . . . .
C15 C 0.6443(2) 0.34842(11) 0.89204(16) 0.0434(5) Uani 1 1 d . . . . .
H15A H 0.701111 0.356166 0.836168 0.052 Uiso 1 1 calc R U . . .
C16 C 0.6010(3) 0.27895(14) 0.8863(3) 0.0693(8) Uani 1 1 d . . . . .
H16A H 0.673571 0.250213 0.893950 0.104 Uiso 1 1 calc R U . . .
H16B H 0.542646 0.270490 0.939032 0.104 Uiso 1 1 calc R U . . .
H16C H 0.558571 0.271167 0.822293 0.104 Uiso 1 1 calc R U . . .
C17 C 0.7201(3) 0.35915(15) 0.9877(2) 0.0662(8) Uani 1 1 d . . . . .
H17A H 0.748096 0.404161 0.991250 0.099 Uiso 1 1 calc R U . . .
H17B H 0.667711 0.349667 1.043778 0.099 Uiso 1 1 calc R U . . .
H17C H 0.793258 0.330534 0.989549 0.099 Uiso 1 1 calc R U . . .
C18 C 0.3808(2) 0.50976(10) 0.69054(16) 0.0415(5) Uani 1 1 d . . . . .
H18A H 0.443764 0.496883 0.641299 0.050 Uiso 1 1 calc R U . . .
C19 C 0.2513(3) 0.49400(16) 0.6471(2) 0.0676(8) Uani 1 1 d . . . . .
H19A H 0.236013 0.519212 0.586868 0.101 Uiso 1 1 calc R U . . .
H19B H 0.246551 0.447875 0.631536 0.101 Uiso 1 1 calc R U . . .
H19C H 0.187876 0.504767 0.694999 0.101 Uiso 1 1 calc R U . . .
C20 C 0.3946(3) 0.58198(12) 0.7085(2) 0.0626(7) Uani 1 1 d . . . . .
H20A H 0.376215 0.605331 0.646917 0.094 Uiso 1 1 calc R U . . .
H20B H 0.335792 0.595608 0.758347 0.094 Uiso 1 1 calc R U . . .
H20C H 0.480523 0.591493 0.731714 0.094 Uiso 1 1 calc R U . . .
C21 C 0.59932(19) 0.19568(9) 0.46062(14) 0.0328(4) Uani 1 1 d . . . . .
C22 C 0.5827(2) 0.18587(10) 0.35906(15) 0.0382(5) Uani 1 1 d . . . . .
C23 C 0.5373(2) 0.12644(11) 0.32680(16) 0.0483(6) Uani 1 1 d . . . . .
H23A H 0.525672 0.118745 0.258146 0.058 Uiso 1 1 calc R U . . .
C24 C 0.5088(3) 0.07861(11) 0.39239(18) 0.0516(6) Uani 1 1 d . . . . .
H24A H 0.478051 0.038226 0.368882 0.062 Uiso 1 1 calc R U . . .
C25 C 0.5247(2) 0.08908(11) 0.49225(17) 0.0472(6) Uani 1 1 d . . . . .
H25A H 0.505337 0.055460 0.536806 0.057 Uiso 1 1 calc R U . . .
C26 C 0.5684(2) 0.14770(10) 0.52912(15) 0.0365(5) Uani 1 1 d . . . . .
C27 C 0.5856(2) 0.15908(11) 0.63890(15) 0.0426(5) Uani 1 1 d . . . . .
H27A H 0.586541 0.206816 0.649765 0.051 Uiso 1 1 calc R U . . .
C28 C 0.7093(3) 0.1331(2) 0.6765(2) 0.0851(11) Uani 1 1 d . . . . .
H28A H 0.718460 0.140994 0.747560 0.128 Uiso 1 1 calc R U . . .
H28B H 0.713046 0.086627 0.663834 0.128 Uiso 1 1 calc R U . . .
H28C H 0.777270 0.154816 0.642785 0.128 Uiso 1 1 calc R U . . .
C29 C 0.4794(3) 0.13142(18) 0.6978(2) 0.0805(10) Uani 1 1 d . . . . .
H29A H 0.399267 0.148781 0.672412 0.121 Uiso 1 1 calc R U . . .
H29B H 0.478903 0.084294 0.691662 0.121 Uiso 1 1 calc R U . . .
H29C H 0.491768 0.143345 0.767272 0.121 Uiso 1 1 calc R U . . .
C30 C 0.6085(3) 0.23716(11) 0.28324(16) 0.0473(6) Uani 1 1 d . . . . .
H30A H 0.639142 0.276611 0.318965 0.057 Uiso 1 1 calc R U . . .
C31 C 0.7108(4) 0.21544(17) 0.2145(2) 0.0827(10) Uani 1 1 d . . . . .
H31A H 0.725758 0.249454 0.166157 0.124 Uiso 1 1 calc R U . . .
H31B H 0.788343 0.207013 0.253116 0.124 Uiso 1 1 calc R U . . .
H31C H 0.684006 0.175937 0.180181 0.124 Uiso 1 1 calc R U . . .
C32 C 0.4891(3) 0.25490(14) 0.2252(2) 0.0699(9) Uani 1 1 d . . . . .
H32A H 0.507848 0.288154 0.176573 0.105 Uiso 1 1 calc R U . . .
H32B H 0.455597 0.216537 0.191374 0.105 Uiso 1 1 calc R U . . .
H32C H 0.426992 0.271453 0.270365 0.105 Uiso 1 1 calc R U . . .
C33 C 0.3927(2) 0.35627(14) 0.49861(18) 0.0557(7) Uani 1 1 d . . . . .
H33A H 0.373144 0.315813 0.527162 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N1 1.6641(16) . ?
P1 O1 1.7311(15) . ?
P1 C1 1.817(2) . ?
N1 C9 1.441(2) . ?
N1 C7 1.462(3) . ?
N2 C8 1.265(3) . ?
N2 C21 1.425(2) . ?
O1 C33 1.327(3) . ?
O2 C33 1.191(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.406(3) . ?
C2 C3 1.392(3) . ?
C2 C8 1.461(3) . ?
C3 C4 1.380(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.392(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.498(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9500 . ?
C9 C10 1.393(3) . ?
C9 C14 1.404(3) . ?
C10 C11 1.394(3) . ?
C10 C18 1.513(3) . ?
C11 C12 1.368(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.373(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.513(3) . ?
C15 C16 1.513(4) . ?
C15 C17 1.523(3) . ?
C15 H15A 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.519(4) . ?
C18 C20 1.523(3) . ?
C18 H18A 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.400(3) . ?
C21 C26 1.408(3) . ?
C22 C23 1.389(3) . ?
C22 C30 1.511(3) . ?
C23 C24 1.374(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.378(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.389(3) . ?
C25 H25A 0.9500 . ?
C26 C27 1.515(3) . ?
C27 C28 1.500(4) . ?
C27 C29 1.520(4) . ?
C27 H27A 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C32 1.520(4) . ?
C30 C31 1.528(4) . ?
C30 H30A 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 O1 103.32(8) . . ?
N1 P1 C1 89.30(9) . . ?
O1 P1 C1 95.31(8) . . ?
C9 N1 C7 118.63(15) . . ?
C9 N1 P1 122.49(13) . . ?
C7 N1 P1 118.72(13) . . ?
C8 N2 C21 119.63(17) . . ?
C33 O1 P1 118.18(16) . . ?
C6 C1 C2 120.01(18) . . ?
C6 C1 P1 111.81(14) . . ?
C2 C1 P1 128.17(15) . . ?
C3 C2 C1 118.36(18) . . ?
C3 C2 C8 120.16(19) . . ?
C1 C2 C8 121.44(18) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 119.24(19) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C1 C6 C5 120.69(19) . . ?
C1 C6 C7 113.99(17) . . ?
C5 C6 C7 125.32(18) . . ?
N1 C7 C6 105.01(16) . . ?
N1 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
N1 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
N2 C8 C2 121.54(19) . . ?
N2 C8 H8A 119.2 . . ?
C2 C8 H8A 119.2 . . ?
C10 C9 C14 122.05(18) . . ?
C10 C9 N1 119.49(17) . . ?
C14 C9 N1 118.46(18) . . ?
C9 C10 C11 117.7(2) . . ?
C9 C10 C18 122.32(18) . . ?
C11 C10 C18 119.9(2) . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C14 121.2(2) . . ?
C12 C13 H13A 119.4 . . ?
C14 C13 H13A 119.4 . . ?
C13 C14 C9 117.4(2) . . ?
C13 C14 C15 119.98(19) . . ?
C9 C14 C15 122.59(19) . . ?
C16 C15 C14 111.3(2) . . ?
C16 C15 C17 109.6(2) . . ?
C14 C15 C17 112.4(2) . . ?
C16 C15 H15A 107.8 . . ?
C14 C15 H15A 107.8 . . ?
C17 C15 H15A 107.8 . . ?
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 . . ?
C10 C18 C19 111.2(2) . . ?
C10 C18 C20 111.22(19) . . ?
C19 C18 C20 110.8(2) . . ?
C10 C18 H18A 107.8 . . ?
C19 C18 H18A 107.8 . . ?
C20 C18 H18A 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 121.59(18) . . ?
C22 C21 N2 121.28(18) . . ?
C26 C21 N2 117.01(17) . . ?
C23 C22 C21 118.09(19) . . ?
C23 C22 C30 118.56(19) . . ?
C21 C22 C30 123.33(18) . . ?
C24 C23 C22 121.2(2) . . ?
C24 C23 H23A 119.4 . . ?
C22 C23 H23A 119.4 . . ?
C23 C24 C25 120.1(2) . . ?
C23 C24 H24A 119.9 . . ?
C25 C24 H24A 119.9 . . ?
C24 C25 C26 121.4(2) . . ?
C24 C25 H25A 119.3 . . ?
C26 C25 H25A 119.3 . . ?
C25 C26 C21 117.56(19) . . ?
C25 C26 C27 121.29(19) . . ?
C21 C26 C27 121.13(18) . . ?
C28 C27 C26 110.8(2) . . ?
C28 C27 C29 110.4(2) . . ?
C26 C27 C29 113.1(2) . . ?
C28 C27 H27A 107.4 . . ?
C26 C27 H27A 107.4 . . ?
C29 C27 H27A 107.4 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C22 C30 C32 110.8(2) . . ?
C22 C30 C31 111.1(2) . . ?
C32 C30 C31 111.0(2) . . ?
C22 C30 H30A 108.0 . . ?
C32 C30 H30A 108.0 . . ?
C31 C30 H30A 108.0 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O2 C33 O1 123.2(3) . . ?
O2 C33 H33A 118.4 . . ?
O1 C33 H33A 118.4 . . ?

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
O1 P1 N1 C9 100.01(16) . . . . ?
C1 P1 N1 C9 -164.70(16) . . . . ?
O1 P1 N1 C7 -84.73(16) . . . . ?
C1 P1 N1 C7 10.56(15) . . . . ?
N1 P1 O1 C33 -131.36(18) . . . . ?
C1 P1 O1 C33 138.10(18) . . . . ?
N1 P1 C1 C6 -6.08(14) . . . . ?
O1 P1 C1 C6 97.24(14) . . . . ?
N1 P1 C1 C2 173.04(18) . . . . ?
O1 P1 C1 C2 -83.64(18) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
P1 C1 C2 C3 -179.20(15) . . . . ?
C6 C1 C2 C8 177.73(17) . . . . ?
P1 C1 C2 C8 -1.3(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C8 C2 C3 C4 -178.26(18) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
P1 C1 C6 C5 179.93(15) . . . . ?
C2 C1 C6 C7 -178.56(17) . . . . ?
P1 C1 C6 C7 0.6(2) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 178.40(19) . . . . ?
C9 N1 C7 C6 163.86(16) . . . . ?
P1 N1 C7 C6 -11.6(2) . . . . ?
C1 C6 C7 N1 6.1(2) . . . . ?
C5 C6 C7 N1 -173.13(18) . . . . ?
C21 N2 C8 C2 -179.26(17) . . . . ?
C3 C2 C8 N2 -174.21(19) . . . . ?
C1 C2 C8 N2 8.0(3) . . . . ?
C7 N1 C9 C10 85.3(2) . . . . ?
P1 N1 C9 C10 -99.4(2) . . . . ?
C7 N1 C9 C14 -94.2(2) . . . . ?
P1 N1 C9 C14 81.0(2) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
N1 C9 C10 C11 179.63(19) . . . . ?
C14 C9 C10 C18 178.90(19) . . . . ?
N1 C9 C10 C18 -0.6(3) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C18 C10 C11 C12 -179.7(2) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C9 -0.9(4) . . . . ?
C12 C13 C14 C15 179.6(2) . . . . ?
C10 C9 C14 C13 1.3(3) . . . . ?
N1 C9 C14 C13 -179.19(19) . . . . ?
C10 C9 C14 C15 -179.2(2) . . . . ?
N1 C9 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 75.5(3) . . . . ?
C9 C14 C15 C16 -104.0(3) . . . . ?
C13 C14 C15 C17 -47.9(3) . . . . ?
C9 C14 C15 C17 132.6(2) . . . . ?
C9 C10 C18 C19 119.6(2) . . . . ?
C11 C10 C18 C19 -60.7(3) . . . . ?
C9 C10 C18 C20 -116.4(2) . . . . ?
C11 C10 C18 C20 63.3(3) . . . . ?
C8 N2 C21 C22 -68.4(3) . . . . ?
C8 N2 C21 C26 115.5(2) . . . . ?
C26 C21 C22 C23 -1.5(3) . . . . ?
N2 C21 C22 C23 -177.4(2) . . . . ?
C26 C21 C22 C30 176.8(2) . . . . ?
N2 C21 C22 C30 1.0(3) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C30 C22 C23 C24 -178.2(2) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
C23 C24 C25 C26 0.6(4) . . . . ?
C24 C25 C26 C21 -1.7(4) . . . . ?
C24 C25 C26 C27 179.9(2) . . . . ?
C22 C21 C26 C25 2.2(3) . . . . ?
N2 C21 C26 C25 178.3(2) . . . . ?
C22 C21 C26 C27 -179.4(2) . . . . ?
N2 C21 C26 C27 -3.4(3) . . . . ?
C25 C26 C27 C28 83.2(3) . . . . ?
C21 C26 C27 C28 -95.1(3) . . . . ?
C25 C26 C27 C29 -41.3(3) . . . . ?
C21 C26 C27 C29 140.4(2) . . . . ?
C23 C22 C30 C32 61.2(3) . . . . ?
C21 C22 C30 C32 -117.2(3) . . . . ?
C23 C22 C30 C31 -62.7(3) . . . . ?
C21 C22 C30 C31 119.0(3) . . . . ?
P1 O1 C33 O2 175.9(2) . . . . ?

_refine_diff_density_max         0.678
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.058

