# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_P-1
_database_code_depnum_ccdc_archive 'CCDC 2106632'
loop_
_audit_author_name
_audit_author_address
'Eunji Jin'
;Ulsan National Institute and Science and Technology
South Korea
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        PN-TPN
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 N P'
_chemical_formula_weight         453.49

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   9.4530(19)
_cell_length_b                   10.884(2)
_cell_length_c                   13.043(3)
_cell_angle_alpha                104.06(3)
_cell_angle_beta                 110.34(3)
_cell_angle_gamma                96.49(3)
_cell_volume                     1191.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11683
_cell_measurement_theta_min      1.747
_cell_measurement_theta_max      27.485

_exptl_crystal_description       hexahedron
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11683
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.747
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5444
_reflns_number_gt                3920
_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       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  CIFTAB
_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)+(0.0413P)²+0.8077P] 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         5444
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
N1 N 0.7151(2) -0.05179(18) 0.29279(16) 0.0287(4) Uani 1 1 d . . . . .
P1 P 0.59835(7) 0.05274(6) 0.31540(5) 0.02772(15) Uani 1 1 d . . . . .
C1 C 0.6067(2) 0.1390(2) 0.21326(18) 0.0253(5) Uani 1 1 d . . . . .
C2 C 0.4757(2) 0.2059(2) 0.17879(19) 0.0264(5) Uani 1 1 d . . . . .
C3 C 0.4342(3) 0.2811(2) 0.2623(2) 0.0321(5) Uani 1 1 d . . . . .
H3 H 0.4939 0.2942 0.3411 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3070(3) 0.3369(2) 0.2318(2) 0.0365(6) Uani 1 1 d . . . . .
H4 H 0.2817 0.3896 0.2897 0.044 Uiso 1 1 calc R U . . .
C5 C 0.2172(3) 0.3164(2) 0.1180(2) 0.0364(6) Uani 1 1 d . . . . .
H5 H 0.1288 0.3530 0.0973 0.044 Uiso 1 1 calc R U . . .
C6 C 0.2565(3) 0.2422(2) 0.0342(2) 0.0369(6) Uani 1 1 d . . . . .
H6 H 0.1953 0.2284 -0.0445 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3845(3) 0.1877(2) 0.0643(2) 0.0327(5) Uani 1 1 d . . . . .
H7 H 0.4106 0.1370 0.0059 0.039 Uiso 1 1 calc R U . . .
C8 C 0.7196(2) 0.1393(2) 0.17132(18) 0.0264(5) Uani 1 1 d . . . . .
C9 C 0.7292(2) 0.2225(2) 0.09695(19) 0.0270(5) Uani 1 1 d . . . . .
C10 C 0.7644(3) 0.3563(2) 0.1424(2) 0.0347(5) Uani 1 1 d . . . . .
H10 H 0.7815 0.3947 0.2205 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7749(3) 0.4350(2) 0.0750(2) 0.0429(6) Uani 1 1 d . . . . .
H11 H 0.7989 0.5267 0.1070 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7506(3) 0.3801(3) -0.0383(2) 0.0458(7) Uani 1 1 d . . . . .
H12 H 0.7588 0.4341 -0.0843 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7145(3) 0.2470(3) -0.0852(2) 0.0424(6) Uani 1 1 d . . . . .
H13 H 0.6962 0.2092 -0.1636 0.051 Uiso 1 1 calc R U . . .
C14 C 0.7051(3) 0.1686(2) -0.0177(2) 0.0346(5) Uani 1 1 d . . . . .
H14 H 0.6819 0.0769 -0.0500 0.042 Uiso 1 1 calc R U . . .
C15 C 0.8443(2) 0.0683(2) 0.20295(19) 0.0266(5) Uani 1 1 d . . . . .
C16 C 0.9717(3) 0.0910(2) 0.1724(2) 0.0333(5) Uani 1 1 d . . . . .
H16 H 0.9764 0.1533 0.1332 0.040 Uiso 1 1 calc R U . . .
C17 C 1.0895(3) 0.0256(3) 0.1977(2) 0.0392(6) Uani 1 1 d . . . . .
H17 H 1.1738 0.0425 0.1758 0.047 Uiso 1 1 calc R U . . .
C18 C 1.0843(3) -0.0648(3) 0.2553(2) 0.0379(6) Uani 1 1 d . . . . .
H18 H 1.1651 -0.1105 0.2728 0.045 Uiso 1 1 calc R U . . .
C19 C 0.9615(3) -0.0891(2) 0.2875(2) 0.0326(5) Uani 1 1 d . . . . .
H19 H 0.9592 -0.1511 0.3275 0.039 Uiso 1 1 calc R U . . .
C20 C 0.8413(2) -0.0236(2) 0.26209(19) 0.0270(5) Uani 1 1 d . . . . .
C21 C 0.7004(3) -0.1632(2) 0.3325(2) 0.0298(5) Uani 1 1 d . . . . .
C22 C 0.6389(3) -0.2854(2) 0.2540(2) 0.0361(6) Uani 1 1 d . . . . .
H22 H 0.6089 -0.2961 0.1744 0.043 Uiso 1 1 calc R U . . .
C23 C 0.6208(3) -0.3927(3) 0.2917(3) 0.0435(7) Uani 1 1 d . . . . .
H23 H 0.5774 -0.4768 0.2378 0.052 Uiso 1 1 calc R U . . .
C24 C 0.6660(3) -0.3773(3) 0.4076(3) 0.0488(7) Uani 1 1 d . . . . .
H24 H 0.6534 -0.4508 0.4333 0.059 Uiso 1 1 calc R U . . .
C25 C 0.7290(3) -0.2560(3) 0.4856(3) 0.0474(7) Uani 1 1 d . . . . .
H25 H 0.7607 -0.2458 0.5653 0.057 Uiso 1 1 calc R U . . .
C26 C 0.7466(3) -0.1482(3) 0.4486(2) 0.0370(6) Uani 1 1 d . . . . .
H26 H 0.7902 -0.0643 0.5028 0.044 Uiso 1 1 calc R U . . .
C27 C 0.7154(3) 0.1833(2) 0.44995(19) 0.0300(5) Uani 1 1 d . . . . .
C28 C 0.8545(3) 0.2626(3) 0.4714(2) 0.0395(6) Uani 1 1 d . . . . .
H28 H 0.8993 0.2473 0.4159 0.047 Uiso 1 1 calc R U . . .
C29 C 0.9289(3) 0.3633(3) 0.5721(2) 0.0492(7) Uani 1 1 d . . . . .
H29 H 1.0251 0.4157 0.5860 0.059 Uiso 1 1 calc R U . . .
C30 C 0.8638(3) 0.3882(3) 0.6529(2) 0.0498(7) Uani 1 1 d . . . . .
H30 H 0.9139 0.4585 0.7215 0.060 Uiso 1 1 calc R U . . .
C31 C 0.7263(4) 0.3106(3) 0.6332(2) 0.0477(7) Uani 1 1 d . . . . .
H31 H 0.6811 0.3274 0.6884 0.057 Uiso 1 1 calc R U . . .
C32 C 0.6530(3) 0.2080(3) 0.5333(2) 0.0387(6) Uani 1 1 d . . . . .
H32 H 0.5591 0.1538 0.5214 0.046 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
N1 C20 1.410(3) . ?
N1 C21 1.440(3) . ?
N1 P1 1.7163(19) . ?
P1 C1 1.823(2) . ?
P1 C27 1.846(3) . ?
C1 C8 1.359(3) . ?
C1 C2 1.497(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.375(4) . ?
C5 C6 1.381(4) . ?
C6 C7 1.384(3) . ?
C8 C15 1.476(3) . ?
C8 C9 1.496(3) . ?
C9 C10 1.385(3) . ?
C9 C14 1.393(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.378(4) . ?
C12 C13 1.380(4) . ?
C13 C14 1.383(3) . ?
C15 C20 1.408(3) . ?
C15 C16 1.408(3) . ?
C16 C17 1.376(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.384(3) . ?
C19 C20 1.395(3) . ?
C21 C22 1.380(3) . ?
C21 C26 1.383(3) . ?
C22 C23 1.388(3) . ?
C23 C24 1.380(4) . ?
C24 C25 1.371(4) . ?
C25 C26 1.387(3) . ?
C27 C28 1.386(3) . ?
C27 C32 1.394(3) . ?
C28 C29 1.381(4) . ?
C29 C30 1.382(4) . ?
C30 C31 1.372(4) . ?
C31 C32 1.384(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
C20 N1 C21 118.41(18) . . ?
C20 N1 P1 125.02(15) . . ?
C21 N1 P1 115.16(14) . . ?
N1 P1 C1 98.77(9) . . ?
N1 P1 C27 106.90(10) . . ?
C1 P1 C27 98.93(10) . . ?
C8 C1 C2 123.80(19) . . ?
C8 C1 P1 122.70(16) . . ?
C2 C1 P1 113.49(15) . . ?
C7 C2 C3 117.9(2) . . ?
C7 C2 C1 122.0(2) . . ?
C3 C2 C1 119.9(2) . . ?
C4 C3 C2 120.9(2) . . ?
C5 C4 C3 120.3(2) . . ?
C4 C5 C6 119.6(2) . . ?
C5 C6 C7 120.2(2) . . ?
C6 C7 C2 121.1(2) . . ?
C1 C8 C15 122.9(2) . . ?
C1 C8 C9 120.12(19) . . ?
C15 C8 C9 116.75(18) . . ?
C10 C9 C14 118.6(2) . . ?
C10 C9 C8 119.9(2) . . ?
C14 C9 C8 121.5(2) . . ?
C9 C10 C11 120.7(2) . . ?
C12 C11 C10 120.0(2) . . ?
C11 C12 C13 120.1(2) . . ?
C12 C13 C14 119.9(2) . . ?
C13 C14 C9 120.7(2) . . ?
C20 C15 C16 117.7(2) . . ?
C20 C15 C8 122.70(19) . . ?
C16 C15 C8 119.6(2) . . ?
C17 C16 C15 122.0(2) . . ?
C16 C17 C18 119.5(2) . . ?
C17 C18 C19 120.2(2) . . ?
C18 C19 C20 120.8(2) . . ?
C19 C20 C15 119.83(19) . . ?
C19 C20 N1 120.2(2) . . ?
C15 C20 N1 119.98(19) . . ?
C22 C21 C26 119.9(2) . . ?
C22 C21 N1 119.7(2) . . ?
C26 C21 N1 120.4(2) . . ?
C21 C22 C23 119.9(2) . . ?
C24 C23 C22 120.0(3) . . ?
C25 C24 C23 120.0(2) . . ?
C24 C25 C26 120.3(3) . . ?
C21 C26 C25 119.8(3) . . ?
C28 C27 C32 118.0(2) . . ?
C28 C27 P1 125.31(18) . . ?
C32 C27 P1 116.54(19) . . ?
C29 C28 C27 121.1(2) . . ?
C28 C29 C30 120.2(3) . . ?
C31 C30 C29 119.6(3) . . ?
C30 C31 C32 120.4(2) . . ?
C31 C32 C27 120.8(3) . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_P-1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2106638'
loop_
_audit_author_name
_audit_author_address
'Eunji Jin'
;Ulsan National Institute and Science and Technology
South Korea
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 N O P'
_chemical_formula_weight         469.49

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   10.347(2)
_cell_length_b                   11.030(2)
_cell_length_c                   11.987(2)
_cell_angle_alpha                69.43(3)
_cell_angle_beta                 86.51(3)
_cell_angle_gamma                71.10(3)
_cell_volume                     1209.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11934
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      0.998

_exptl_crystal_description       hexahedron
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.099
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11934
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5544
_reflns_number_gt                4291
_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       'Rigaku Rapid Auto'
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  CIFTAB
_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)+(0.0294P)²+0.7245P] 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         5544
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
N1 N 0.77517(15) 0.54033(15) 0.08726(13) 0.0204(3) Uani 1 1 d . . . . .
O1 O 0.65705(12) 0.57310(12) 0.28371(11) 0.0237(3) Uani 1 1 d . . . . .
P1 P 0.74876(4) 0.47399(5) 0.23372(4) 0.01727(11) Uani 1 1 d . . . . .
C1 C 0.69353(16) 0.34330(17) 0.21150(16) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.67664(16) 0.37676(17) 0.08190(15) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.62095(17) 0.31724(18) 0.01977(16) 0.0213(4) Uani 1 1 d . . . . .
H3 H 0.5876 0.2440 0.0627 0.026 Uiso 1 1 calc R U . . .
C4 C 0.61399(18) 0.36407(19) -0.10367(17) 0.0251(4) Uani 1 1 d . . . . .
H4 H 0.5765 0.3228 -0.1451 0.030 Uiso 1 1 calc R U . . .
C5 C 0.66191(18) 0.4717(2) -0.16697(17) 0.0263(4) Uani 1 1 d . . . . .
H5 H 0.6585 0.5021 -0.2517 0.032 Uiso 1 1 calc R U . . .
C6 C 0.71445(18) 0.53509(19) -0.10835(16) 0.0231(4) Uani 1 1 d . . . . .
H6 H 0.7451 0.6099 -0.1522 0.028 Uiso 1 1 calc R U . . .
C7 C 0.72161(16) 0.48743(18) 0.01554(15) 0.0189(4) Uani 1 1 d . . . . .
C8 C 0.81115(18) 0.66309(18) 0.03979(16) 0.0209(4) Uani 1 1 d . . . . .
C9 C 0.7166(2) 0.7863(2) -0.02829(18) 0.0287(4) Uani 1 1 d . . . . .
H9 H 0.6263 0.7903 -0.0445 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7542(2) 0.9035(2) -0.07251(19) 0.0334(5) Uani 1 1 d . . . . .
H10 H 0.6897 0.9876 -0.1198 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8853(2) 0.8984(2) -0.04798(18) 0.0308(4) Uani 1 1 d . . . . .
H11 H 0.9107 0.9789 -0.0784 0.037 Uiso 1 1 calc R U . . .
C12 C 0.97883(19) 0.7765(2) 0.02065(18) 0.0284(4) Uani 1 1 d . . . . .
H12 H 1.0685 0.7732 0.0380 0.034 Uiso 1 1 calc R U . . .
C13 C 0.94224(18) 0.65864(19) 0.06442(17) 0.0247(4) Uani 1 1 d . . . . .
H13 H 1.0071 0.5746 0.1114 0.030 Uiso 1 1 calc R U . . .
C14 C 0.91303(17) 0.38872(17) 0.31380(15) 0.0187(3) Uani 1 1 d . . . . .
C15 C 1.01938(18) 0.30196(18) 0.27276(16) 0.0236(4) Uani 1 1 d . . . . .
H15 H 1.0074 0.2928 0.1985 0.028 Uiso 1 1 calc R U . . .
C16 C 1.14180(19) 0.2296(2) 0.33974(18) 0.0288(4) Uani 1 1 d . . . . .
H16 H 1.2143 0.1713 0.3112 0.035 Uiso 1 1 calc R U . . .
C17 C 1.1590(2) 0.2418(2) 0.44873(19) 0.0326(5) Uani 1 1 d . . . . .
H17 H 1.2432 0.1915 0.4949 0.039 Uiso 1 1 calc R U . . .
C18 C 1.0542(2) 0.3268(2) 0.49032(18) 0.0325(5) Uani 1 1 d . . . . .
H18 H 1.0663 0.3345 0.5652 0.039 Uiso 1 1 calc R U . . .
C19 C 0.93109(19) 0.4010(2) 0.42288(17) 0.0260(4) Uani 1 1 d . . . . .
H19 H 0.8593 0.4600 0.4513 0.031 Uiso 1 1 calc R U . . .
C20 C 0.68425(16) 0.23375(17) 0.30363(15) 0.0174(3) Uani 1 1 d . . . . .
C21 C 0.70431(17) 0.22267(17) 0.42977(15) 0.0184(3) Uani 1 1 d . . . . .
C22 C 0.81389(18) 0.11663(18) 0.50197(16) 0.0230(4) Uani 1 1 d . . . . .
H22 H 0.8712 0.0496 0.4721 0.028 Uiso 1 1 calc R U . . .
C23 C 0.8393(2) 0.1088(2) 0.61642(17) 0.0276(4) Uani 1 1 d . . . . .
H23 H 0.9161 0.0385 0.6639 0.033 Uiso 1 1 calc R U . . .
C24 C 0.7530(2) 0.2033(2) 0.66253(17) 0.0283(4) Uani 1 1 d . . . . .
H24 H 0.7713 0.1981 0.7411 0.034 Uiso 1 1 calc R U . . .
C25 C 0.6407(2) 0.30464(19) 0.59394(17) 0.0268(4) Uani 1 1 d . . . . .
H25 H 0.5796 0.3672 0.6264 0.032 Uiso 1 1 calc R U . . .
C26 C 0.61691(18) 0.31525(18) 0.47757(16) 0.0229(4) Uani 1 1 d . . . . .
H26 H 0.5404 0.3862 0.4302 0.027 Uiso 1 1 calc R U . . .
C27 C 0.65796(17) 0.11344(17) 0.29140(15) 0.0194(4) Uani 1 1 d . . . . .
C28 C 0.54253(18) 0.08074(18) 0.33876(17) 0.0233(4) Uani 1 1 d . . . . .
H28 H 0.4808 0.1360 0.3773 0.028 Uiso 1 1 calc R U . . .
C29 C 0.5162(2) -0.0315(2) 0.33060(18) 0.0285(4) Uani 1 1 d . . . . .
H29 H 0.4356 -0.0513 0.3614 0.034 Uiso 1 1 calc R U . . .
C30 C 0.6076(2) -0.1148(2) 0.27740(18) 0.0304(4) Uani 1 1 d . . . . .
H30 H 0.5904 -0.1922 0.2722 0.036 Uiso 1 1 calc R U . . .
C31 C 0.7239(2) -0.0846(2) 0.23196(18) 0.0305(4) Uani 1 1 d . . . . .
H31 H 0.7870 -0.1420 0.1960 0.037 Uiso 1 1 calc R U . . .
C32 C 0.74957(19) 0.02904(19) 0.23837(17) 0.0253(4) Uani 1 1 d . . . . .
H32 H 0.8297 0.0491 0.2065 0.030 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
N1 C7 1.417(2) . ?
N1 C8 1.434(2) . ?
N1 P1 1.6914(16) . ?
O1 P1 1.4743(13) . ?
P1 C14 1.7955(19) . ?
P1 C1 1.8158(17) . ?
C1 C20 1.347(2) . ?
C1 C2 1.473(2) . ?
C2 C3 1.399(2) . ?
C2 C7 1.407(2) . ?
C3 C4 1.383(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.388(2) . ?
C8 C13 1.387(2) . ?
C8 C9 1.388(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.378(3) . ?
C12 C13 1.387(3) . ?
C14 C19 1.390(3) . ?
C14 C15 1.397(3) . ?
C15 C16 1.380(3) . ?
C16 C17 1.387(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.390(3) . ?
C20 C27 1.494(2) . ?
C20 C21 1.495(2) . ?
C21 C26 1.392(2) . ?
C21 C22 1.397(3) . ?
C22 C23 1.380(3) . ?
C23 C24 1.389(3) . ?
C24 C25 1.380(3) . ?
C25 C26 1.389(3) . ?
C27 C28 1.390(2) . ?
C27 C32 1.393(3) . ?
C28 C29 1.387(3) . ?
C29 C30 1.386(3) . ?
C30 C31 1.382(3) . ?
C31 C32 1.390(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
C7 N1 C8 123.24(15) . . ?
C7 N1 P1 112.89(12) . . ?
C8 N1 P1 121.55(12) . . ?
O1 P1 N1 114.86(8) . . ?
O1 P1 C14 112.14(8) . . ?
N1 P1 C14 107.80(8) . . ?
O1 P1 C1 120.62(8) . . ?
N1 P1 C1 92.41(8) . . ?
C14 P1 C1 106.94(8) . . ?
C20 C1 C2 130.50(16) . . ?
C20 C1 P1 121.78(14) . . ?
C2 C1 P1 107.50(12) . . ?
C3 C2 C7 118.28(16) . . ?
C3 C2 C1 129.39(16) . . ?
C7 C2 C1 112.31(15) . . ?
C4 C3 C2 120.57(17) . . ?
C3 C4 C5 119.94(17) . . ?
C6 C5 C4 120.97(17) . . ?
C5 C6 C7 118.86(17) . . ?
C6 C7 C2 121.35(16) . . ?
C6 C7 N1 125.09(16) . . ?
C2 C7 N1 113.55(15) . . ?
C13 C8 C9 119.62(17) . . ?
C13 C8 N1 119.17(16) . . ?
C9 C8 N1 121.20(16) . . ?
C10 C9 C8 119.91(18) . . ?
C11 C10 C9 120.24(19) . . ?
C12 C11 C10 119.96(18) . . ?
C11 C12 C13 120.09(18) . . ?
C12 C13 C8 120.17(18) . . ?
C19 C14 C15 119.53(17) . . ?
C19 C14 P1 119.33(14) . . ?
C15 C14 P1 120.94(14) . . ?
C16 C15 C14 120.21(18) . . ?
C15 C16 C17 119.99(18) . . ?
C18 C17 C16 120.22(18) . . ?
C17 C18 C19 120.12(19) . . ?
C18 C19 C14 119.93(18) . . ?
C1 C20 C27 124.70(16) . . ?
C1 C20 C21 120.96(15) . . ?
C27 C20 C21 114.31(14) . . ?
C26 C21 C22 118.87(17) . . ?
C26 C21 C20 121.89(16) . . ?
C22 C21 C20 119.23(15) . . ?
C23 C22 C21 120.34(17) . . ?
C22 C23 C24 120.28(18) . . ?
C25 C24 C23 119.85(18) . . ?
C24 C25 C26 120.05(17) . . ?
C25 C26 C21 120.50(17) . . ?
C28 C27 C32 118.85(16) . . ?
C28 C27 C20 119.45(15) . . ?
C32 C27 C20 121.64(16) . . ?
C29 C28 C27 120.93(17) . . ?
C30 C29 C28 119.88(18) . . ?
C31 C30 C29 119.63(18) . . ?
C30 C31 C32 120.62(17) . . ?
C31 C32 C27 120.07(17) . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.048

