# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1554053'
_audit_update_record             
;
2017-06-03 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;
_audit_creation_date             2017-05-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/8
_chemical_name_common            ?
_chemical_name_systematic        DCPP
_chemical_formula_moiety         'C30 H21 N2 P'
_chemical_formula_sum            'C30 H21 N2 P'
_chemical_formula_weight         440.46
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5428(13)
_cell_length_b                   10.2866(11)
_cell_length_c                   12.7340(14)
_cell_angle_alpha                68.610(8)
_cell_angle_beta                 85.612(11)
_cell_angle_gamma                72.461(9)
_cell_volume                     1109.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14369
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_min         3.265
_diffrn_ambient_temperature      133.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'rigaku Xtalab P200'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4557
_reflns_number_total             5038
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.3146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0876
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.58195(3) 0.58335(3) 0.12751(2) 0.01551(8) Uani 1 1 d . . . . .
N1 N 0.70269(10) 0.41297(10) 0.19464(8) 0.01729(19) Uani 1 1 d . . . . .
N2 N 0.49204(10) 0.63889(10) 0.23261(7) 0.01686(18) Uani 1 1 d . . . . .
C1 C 0.69747(12) 0.70275(12) 0.07013(9) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.65919(13) 0.84016(12) 0.07957(10) 0.0216(2) Uani 1 1 d . . . . .
H2 H 0.5869 0.8625 0.1310 0.026 Uiso 1 1 calc R . . . .
C3 C 0.72652(14) 0.94480(13) 0.01395(11) 0.0267(3) Uani 1 1 d . . . . .
H3 H 0.7006 1.0376 0.0214 0.032 Uiso 1 1 calc R . . . .
C4 C 0.83096(14) 0.91376(14) -0.06203(10) 0.0271(3) Uani 1 1 d . . . . .
H4 H 0.8753 0.9858 -0.1077 0.032 Uiso 1 1 calc R . . . .
C5 C 0.87071(13) 0.77694(14) -0.07122(10) 0.0252(2) Uani 1 1 d . . . . .
H5 H 0.9440 0.7548 -0.1221 0.030 Uiso 1 1 calc R . . . .
C6 C 0.80402(12) 0.67233(13) -0.00648(9) 0.0211(2) Uani 1 1 d . . . . .
H6 H 0.8308 0.5796 -0.0142 0.025 Uiso 1 1 calc R . . . .
C7 C 0.84398(12) 0.35875(12) 0.24810(8) 0.0170(2) Uani 1 1 d . . . . .
C8 C 0.94696(12) 0.43158(12) 0.24574(9) 0.0195(2) Uani 1 1 d . . . . .
H8 H 0.9257 0.5338 0.2060 0.023 Uiso 1 1 calc R . . . .
C9 C 1.08125(13) 0.35038(13) 0.30304(10) 0.0230(2) Uani 1 1 d . . . . .
H9 H 1.1520 0.3985 0.3031 0.028 Uiso 1 1 calc R . . . .
C10 C 1.11491(13) 0.19986(14) 0.36052(10) 0.0248(2) Uani 1 1 d . . . . .
H10 H 1.2077 0.1470 0.3991 0.030 Uiso 1 1 calc R . . . .
C11 C 1.01365(13) 0.12708(13) 0.36154(9) 0.0228(2) Uani 1 1 d . . . . .
H11 H 1.0367 0.0244 0.4001 0.027 Uiso 1 1 calc R . . . .
C12 C 0.87732(12) 0.20654(12) 0.30522(9) 0.0185(2) Uani 1 1 d . . . . .
C13 C 0.75234(12) 0.16361(12) 0.28807(9) 0.0187(2) Uani 1 1 d . . . . .
C14 C 0.71986(13) 0.03042(13) 0.32713(10) 0.0232(2) Uani 1 1 d . . . . .
H14 H 0.7882 -0.0558 0.3751 0.028 Uiso 1 1 calc R . . . .
C15 C 0.58695(14) 0.02618(13) 0.29493(10) 0.0260(3) Uani 1 1 d . . . . .
H15 H 0.5635 -0.0636 0.3213 0.031 Uiso 1 1 calc R . . . .
C16 C 0.48650(14) 0.15268(13) 0.22399(10) 0.0248(2) Uani 1 1 d . . . . .
H16 H 0.3967 0.1469 0.2014 0.030 Uiso 1 1 calc R . . . .
C17 C 0.51499(13) 0.28691(13) 0.18565(9) 0.0210(2) Uani 1 1 d . . . . .
H17 H 0.4457 0.3729 0.1383 0.025 Uiso 1 1 calc R . . . .
C18 C 0.64902(12) 0.29066(11) 0.21924(9) 0.0171(2) Uani 1 1 d . . . . .
C19 C 0.33663(12) 0.67467(11) 0.23416(9) 0.0183(2) Uani 1 1 d . . . . .
C20 C 0.23865(13) 0.68499(12) 0.15391(10) 0.0226(2) Uani 1 1 d . . . . .
H20 H 0.2722 0.6657 0.0874 0.027 Uiso 1 1 calc R . . . .
C21 C 0.08970(13) 0.72468(13) 0.17510(12) 0.0284(3) Uani 1 1 d . . . . .
H21 H 0.0201 0.7344 0.1211 0.034 Uiso 1 1 calc R . . . .
C22 C 0.03972(13) 0.75054(14) 0.27354(13) 0.0316(3) Uani 1 1 d . . . . .
H22 H -0.0627 0.7754 0.2863 0.038 Uiso 1 1 calc R . . . .
C23 C 0.13753(13) 0.74048(13) 0.35279(12) 0.0279(3) Uani 1 1 d . . . . .
H23 H 0.1034 0.7576 0.4200 0.034 Uiso 1 1 calc R . . . .
C24 C 0.28780(12) 0.70456(12) 0.33205(10) 0.0209(2) Uani 1 1 d . . . . .
C25 C 0.41652(12) 0.68860(12) 0.39363(9) 0.0197(2) Uani 1 1 d . . . . .
C26 C 0.43612(14) 0.70577(13) 0.49474(10) 0.0251(2) Uani 1 1 d . . . . .
H26 H 0.3539 0.7329 0.5374 0.030 Uiso 1 1 calc R . . . .
C27 C 0.57695(15) 0.68264(14) 0.53188(10) 0.0264(3) Uani 1 1 d . . . . .
H27 H 0.5915 0.6946 0.6004 0.032 Uiso 1 1 calc R . . . .
C28 C 0.69807(13) 0.64190(13) 0.46964(9) 0.0230(2) Uani 1 1 d . . . . .
H28 H 0.7941 0.6258 0.4969 0.028 Uiso 1 1 calc R . . . .
C29 C 0.68110(12) 0.62448(12) 0.36863(9) 0.0195(2) Uani 1 1 d . . . . .
H29 H 0.7638 0.5971 0.3264 0.023 Uiso 1 1 calc R . . . .
C30 C 0.53952(12) 0.64835(11) 0.33140(9) 0.0168(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
P1 N1 1.7236(10) . ?
P1 N2 1.7148(9) . ?
P1 C1 1.8154(11) . ?
N1 C7 1.4151(14) . ?
N1 C18 1.4212(13) . ?
N2 C19 1.4167(14) . ?
N2 C30 1.4144(13) . ?
C1 C2 1.3970(16) . ?
C1 C6 1.4009(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3959(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3846(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3892(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3886(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3967(15) . ?
C7 C12 1.4094(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3877(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3950(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3861(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3961(16) . ?
C12 C13 1.4467(15) . ?
C13 C14 1.3985(15) . ?
C13 C18 1.4030(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3801(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3970(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3903(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.3950(15) . ?
C19 C20 1.3918(16) . ?
C19 C24 1.4035(16) . ?
C20 H20 0.9500 . ?
C20 C21 1.3899(17) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.3821(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.3988(16) . ?
C24 C25 1.4432(16) . ?
C25 C26 1.3951(16) . ?
C25 C30 1.4076(15) . ?
C26 H26 0.9500 . ?
C26 C27 1.3816(18) . ?
C27 H27 0.9500 . ?
C27 C28 1.3964(17) . ?
C28 H28 0.9500 . ?
C28 C29 1.3893(15) . ?
C29 H29 0.9500 . ?
C29 C30 1.3869(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 P1 C1 104.91(5) . . ?
N2 P1 N1 105.90(5) . . ?
N2 P1 C1 103.78(5) . . ?
C7 N1 P1 135.72(8) . . ?
C7 N1 C18 106.50(9) . . ?
C18 N1 P1 117.16(7) . . ?
C19 N2 P1 119.31(7) . . ?
C30 N2 P1 133.74(8) . . ?
C30 N2 C19 106.74(9) . . ?
C2 C1 P1 120.51(8) . . ?
C2 C1 C6 118.82(10) . . ?
C6 C1 P1 118.89(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.41(11) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.22(11) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.75(11) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.39(11) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.38(11) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 N1 129.84(10) . . ?
C8 C7 C12 120.67(10) . . ?
C12 C7 N1 109.41(9) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.14(11) . . ?
C9 C8 H8 120.9 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.62(11) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.31(11) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.16(11) . . ?
C12 C11 H11 120.4 . . ?
C7 C12 C13 107.38(10) . . ?
C11 C12 C7 120.10(10) . . ?
C11 C12 C13 132.49(11) . . ?
C14 C13 C12 133.34(11) . . ?
C14 C13 C18 119.88(10) . . ?
C18 C13 C12 106.76(9) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.98(11) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.62(11) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.52(11) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 121.2 . . ?
C16 C17 C18 117.55(11) . . ?
C18 C17 H17 121.2 . . ?
C13 C18 N1 109.93(9) . . ?
C17 C18 N1 128.66(10) . . ?
C17 C18 C13 121.40(10) . . ?
C20 C19 N2 128.69(10) . . ?
C20 C19 C24 121.69(10) . . ?
C24 C19 N2 109.60(9) . . ?
C19 C20 H20 121.4 . . ?
C21 C20 C19 117.27(11) . . ?
C21 C20 H20 121.4 . . ?
C20 C21 H21 119.1 . . ?
C20 C21 C22 121.71(12) . . ?
C22 C21 H21 119.1 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.75(11) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.7 . . ?
C22 C23 C24 118.66(12) . . ?
C24 C23 H23 120.7 . . ?
C19 C24 C25 107.05(9) . . ?
C23 C24 C19 119.87(11) . . ?
C23 C24 C25 133.08(11) . . ?
C26 C25 C24 132.96(11) . . ?
C26 C25 C30 119.80(11) . . ?
C30 C25 C24 107.24(10) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 C25 118.99(11) . . ?
C27 C26 H26 120.5 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.61(11) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.3 . . ?
C29 C28 C27 121.37(11) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 121.1 . . ?
C30 C29 C28 117.85(10) . . ?
C30 C29 H29 121.1 . . ?
C25 C30 N2 109.36(9) . . ?
C29 C30 N2 129.26(10) . . ?
C29 C30 C25 121.38(10) . . ?

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
P1 N1 C7 C8 -13.48(18) . . . . ?
P1 N1 C7 C12 169.91(8) . . . . ?
P1 N1 C18 C13 -171.23(7) . . . . ?
P1 N1 C18 C17 7.77(15) . . . . ?
P1 N2 C19 C20 -6.69(15) . . . . ?
P1 N2 C19 C24 174.88(7) . . . . ?
P1 N2 C30 C25 -174.23(8) . . . . ?
P1 N2 C30 C29 5.92(18) . . . . ?
P1 C1 C2 C3 -164.87(9) . . . . ?
P1 C1 C6 C5 165.28(9) . . . . ?
N1 P1 N2 C19 -122.21(8) . . . . ?
N1 P1 N2 C30 51.70(11) . . . . ?
N1 P1 C1 C2 -136.19(9) . . . . ?
N1 P1 C1 C6 59.16(9) . . . . ?
N1 C7 C8 C9 -177.60(10) . . . . ?
N1 C7 C12 C11 177.83(9) . . . . ?
N1 C7 C12 C13 -0.54(12) . . . . ?
N2 P1 N1 C7 -81.14(11) . . . . ?
N2 P1 N1 C18 88.35(8) . . . . ?
N2 P1 C1 C2 -25.26(10) . . . . ?
N2 P1 C1 C6 170.09(8) . . . . ?
N2 C19 C20 C21 -178.98(10) . . . . ?
N2 C19 C24 C23 -179.00(10) . . . . ?
N2 C19 C24 C25 0.61(12) . . . . ?
C1 P1 N1 C7 28.26(11) . . . . ?
C1 P1 N1 C18 -162.25(8) . . . . ?
C1 P1 N2 C19 127.59(8) . . . . ?
C1 P1 N2 C30 -58.50(11) . . . . ?
C1 C2 C3 C4 0.65(18) . . . . ?
C2 C1 C6 C5 0.37(16) . . . . ?
C2 C3 C4 C5 -1.25(19) . . . . ?
C3 C4 C5 C6 1.41(18) . . . . ?
C4 C5 C6 C1 -0.98(18) . . . . ?
C6 C1 C2 C3 -0.21(17) . . . . ?
C7 N1 C18 C13 1.14(11) . . . . ?
C7 N1 C18 C17 -179.86(11) . . . . ?
C7 C8 C9 C10 0.85(17) . . . . ?
C7 C12 C13 C14 -177.15(12) . . . . ?
C7 C12 C13 C18 1.22(12) . . . . ?
C8 C7 C12 C11 0.86(16) . . . . ?
C8 C7 C12 C13 -177.51(9) . . . . ?
C8 C9 C10 C11 0.08(18) . . . . ?
C9 C10 C11 C12 -0.56(17) . . . . ?
C10 C11 C12 C7 0.10(16) . . . . ?
C10 C11 C12 C13 177.99(11) . . . . ?
C11 C12 C13 C14 4.8(2) . . . . ?
C11 C12 C13 C18 -176.87(11) . . . . ?
C12 C7 C8 C9 -1.32(16) . . . . ?
C12 C13 C14 C15 179.56(11) . . . . ?
C12 C13 C18 N1 -1.47(12) . . . . ?
C12 C13 C18 C17 179.45(10) . . . . ?
C13 C14 C15 C16 0.30(18) . . . . ?
C14 C13 C18 N1 177.17(9) . . . . ?
C14 C13 C18 C17 -1.91(16) . . . . ?
C14 C15 C16 C17 -1.49(18) . . . . ?
C15 C16 C17 C18 0.94(17) . . . . ?
C16 C17 C18 N1 -178.14(10) . . . . ?
C16 C17 C18 C13 0.75(16) . . . . ?
C18 N1 C7 C8 176.26(11) . . . . ?
C18 N1 C7 C12 -0.35(11) . . . . ?
C18 C13 C14 C15 1.35(16) . . . . ?
C19 N2 C30 C25 0.23(11) . . . . ?
C19 N2 C30 C29 -179.62(11) . . . . ?
C19 C20 C21 C22 -1.20(17) . . . . ?
C19 C24 C25 C26 179.22(12) . . . . ?
C19 C24 C25 C30 -0.46(12) . . . . ?
C20 C19 C24 C23 2.44(16) . . . . ?
C20 C19 C24 C25 -177.95(10) . . . . ?
C20 C21 C22 C23 1.41(19) . . . . ?
C21 C22 C23 C24 0.33(19) . . . . ?
C22 C23 C24 C19 -2.20(17) . . . . ?
C22 C23 C24 C25 178.31(12) . . . . ?
C23 C24 C25 C26 -1.2(2) . . . . ?
C23 C24 C25 C30 179.08(12) . . . . ?
C24 C19 C20 C21 -0.71(16) . . . . ?
C24 C25 C26 C27 -179.67(12) . . . . ?
C24 C25 C30 N2 0.14(12) . . . . ?
C24 C25 C30 C29 -179.99(10) . . . . ?
C25 C26 C27 C28 -0.35(18) . . . . ?
C26 C25 C30 N2 -179.59(10) . . . . ?
C26 C25 C30 C29 0.28(16) . . . . ?
C26 C27 C28 C29 0.50(18) . . . . ?
C27 C28 C29 C30 -0.24(17) . . . . ?
C28 C29 C30 N2 179.69(10) . . . . ?
C28 C29 C30 C25 -0.14(16) . . . . ?
C30 N2 C19 C20 177.91(11) . . . . ?
C30 N2 C19 C24 -0.53(12) . . . . ?
C30 C25 C26 C27 -0.02(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_tw
_database_code_depnum_ccdc_archive 'CCDC 1554056'
_audit_update_record             
;
2017-06-03 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;
_audit_creation_date             2017-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        TCP
_chemical_formula_moiety         'C36 H24 N3 P'
_chemical_formula_sum            'C36 H24 N3 P'
_chemical_formula_weight         529.55
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.170(2)
_cell_length_b                   9.1604(10)
_cell_length_c                   17.355(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.830(2)
_cell_angle_gamma                90
_cell_volume                     2689.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8066
_cell_measurement_temperature    133.15
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   REQAB(Rigaku,1998)
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6021
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.085
_diffrn_ambient_temperature      133.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  "'Rigaku Xtalab P200"
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5507
_reflns_number_total             6021
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.8095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1161
_refine_special_details          'Refined as a 2-component twin., Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7264(14)
 0.2736(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26),
  C27(H27), C28(H28), C29(H29), C32(H32), C33(H33), C34(H34), C35(H35)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.24934(2) 0.76286(4) 0.17269(2) 0.02192(11) Uani 1 1 d . . . . .
N1 N 0.30931(7) 0.91097(14) 0.16604(8) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.15639(7) 0.83358(14) 0.15372(8) 0.0242(3) Uani 1 1 d . . . . .
N3 N 0.26507(8) 0.73694(13) 0.27257(8) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.39076(9) 0.88134(17) 0.17183(9) 0.0238(3) Uani 1 1 d . . . . .
C2 C 0.43097(10) 0.75319(19) 0.19611(10) 0.0304(4) Uani 1 1 d . . . . .
H2 H 0.404300 0.670439 0.211914 0.037 Uiso 1 1 calc R . . . .
C3 C 0.51194(11) 0.7516(2) 0.19622(11) 0.0364(4) Uani 1 1 d . . . . .
H3 H 0.541143 0.665454 0.212145 0.044 Uiso 1 1 calc R . . . .
C4 C 0.55136(11) 0.8730(2) 0.17357(12) 0.0401(4) Uani 1 1 d . . . . .
H4 H 0.606851 0.868859 0.174839 0.048 Uiso 1 1 calc R . . . .
C5 C 0.51057(10) 0.9993(2) 0.14930(11) 0.0351(4) Uani 1 1 d . . . . .
H5 H 0.537493 1.081656 0.133396 0.042 Uiso 1 1 calc R . . . .
C6 C 0.42938(9) 1.00419(18) 0.14849(9) 0.0262(3) Uani 1 1 d . . . . .
C7 C 0.36986(9) 1.11500(17) 0.12669(9) 0.0257(3) Uani 1 1 d . . . . .
C8 C 0.37339(11) 1.25709(19) 0.09920(11) 0.0336(4) Uani 1 1 d . . . . .
H8 H 0.422705 1.299151 0.093632 0.040 Uiso 1 1 calc R . . . .
C9 C 0.30438(11) 1.33622(18) 0.08012(11) 0.0366(4) Uani 1 1 d . . . . .
H9 H 0.306174 1.433469 0.061482 0.044 Uiso 1 1 calc R . . . .
C10 C 0.23236(11) 1.27432(18) 0.08803(10) 0.0320(4) Uani 1 1 d . . . . .
H10 H 0.185429 1.329862 0.073490 0.038 Uiso 1 1 calc R . . . .
C11 C 0.22680(10) 1.13388(18) 0.11651(10) 0.0278(3) Uani 1 1 d . . . . .
H11 H 0.177194 1.093153 0.122132 0.033 Uiso 1 1 calc R . . . .
C12 C 0.29649(9) 1.05487(16) 0.13654(9) 0.0229(3) Uani 1 1 d . . . . .
C13 C 0.10906(9) 0.91296(16) 0.19793(10) 0.0253(3) Uani 1 1 d . . . . .
C14 C 0.12961(10) 0.98052(17) 0.26988(10) 0.0283(3) Uani 1 1 d . . . . .
H14 H 0.181959 0.975063 0.298313 0.034 Uiso 1 1 calc R . . . .
C15 C 0.07087(10) 1.05667(18) 0.29904(11) 0.0339(4) Uani 1 1 d . . . . .
H15 H 0.083590 1.104764 0.348074 0.041 Uiso 1 1 calc R . . . .
C16 C -0.00617(11) 1.0640(2) 0.25803(13) 0.0401(4) Uani 1 1 d . . . . .
H16 H -0.045236 1.115804 0.279712 0.048 Uiso 1 1 calc R . . . .
C17 C -0.02627(11) 0.9970(2) 0.18638(12) 0.0386(4) Uani 1 1 d . . . . .
H17 H -0.078743 1.002940 0.158262 0.046 Uiso 1 1 calc R . . . .
C18 C 0.03150(9) 0.92059(18) 0.15583(10) 0.0296(3) Uani 1 1 d . . . . .
C19 C 0.03056(10) 0.84493(19) 0.08284(10) 0.0318(4) Uani 1 1 d . . . . .
C20 C -0.02871(11) 0.8193(2) 0.01821(12) 0.0430(5) Uani 1 1 d . . . . .
H20 H -0.081381 0.851152 0.018190 0.052 Uiso 1 1 calc R . . . .
C21 C -0.00910(12) 0.7473(3) -0.04517(13) 0.0499(5) Uani 1 1 d . . . . .
H21 H -0.048747 0.728683 -0.089366 0.060 Uiso 1 1 calc R . . . .
C22 C 0.06843(13) 0.7009(3) -0.04554(12) 0.0494(5) Uani 1 1 d . . . . .
H22 H 0.080663 0.652962 -0.090525 0.059 Uiso 1 1 calc R . . . .
C23 C 0.12762(12) 0.7231(2) 0.01800(11) 0.0399(4) Uani 1 1 d . . . . .
H23 H 0.180165 0.691013 0.017622 0.048 Uiso 1 1 calc R . . . .
C24 C 0.10748(10) 0.79408(18) 0.08230(10) 0.0284(3) Uani 1 1 d . . . . .
C25 C 0.25131(9) 0.59427(16) 0.29834(9) 0.0237(3) Uani 1 1 d . . . . .
C26 C 0.21383(10) 0.47829(18) 0.25538(10) 0.0303(3) Uani 1 1 d . . . . .
H26 H 0.192391 0.488588 0.201459 0.036 Uiso 1 1 calc R . . . .
C27 C 0.20890(11) 0.34738(19) 0.29403(11) 0.0359(4) Uani 1 1 d . . . . .
H27 H 0.184448 0.265940 0.265796 0.043 Uiso 1 1 calc R . . . .
C28 C 0.23890(11) 0.33235(19) 0.37320(11) 0.0364(4) Uani 1 1 d . . . . .
H28 H 0.233530 0.241777 0.398433 0.044 Uiso 1 1 calc R . . . .
C29 C 0.27646(11) 0.44753(18) 0.41570(10) 0.0318(4) Uani 1 1 d . . . . .
H29 H 0.296842 0.436954 0.469847 0.038 Uiso 1 1 calc R . . . .
C30 C 0.28386(9) 0.57942(17) 0.37763(9) 0.0247(3) Uani 1 1 d . . . . .
C31 C 0.32185(9) 0.71689(17) 0.40219(9) 0.0243(3) Uani 1 1 d . . . . .
C32 C 0.36717(10) 0.76177(19) 0.47240(10) 0.0313(4) Uani 1 1 d . . . . .
H32 H 0.376666 0.697502 0.515952 0.038 Uiso 1 1 calc R . . . .
C33 C 0.39811(10) 0.9012(2) 0.47775(11) 0.0342(4) Uani 1 1 d . . . . .
H33 H 0.429826 0.932889 0.525074 0.041 Uiso 1 1 calc R . . . .
C34 C 0.38303(10) 0.99571(19) 0.41406(10) 0.0328(4) Uani 1 1 d . . . . .
H34 H 0.403901 1.091941 0.419301 0.039 Uiso 1 1 calc R . . . .
C35 C 0.33855(9) 0.95368(17) 0.34331(10) 0.0277(3) Uani 1 1 d . . . . .
H35 H 0.328400 1.019413 0.300426 0.033 Uiso 1 1 calc R . . . .
C36 C 0.30918(8) 0.81142(16) 0.33727(9) 0.0229(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
P1 N1 1.7190(13) . ?
P1 N2 1.7016(13) . ?
P1 N3 1.7246(14) . ?
N1 C1 1.4111(19) . ?
N1 C12 1.4176(19) . ?
N2 C13 1.411(2) . ?
N2 C24 1.420(2) . ?
N3 C25 1.4142(19) . ?
N3 C36 1.4177(19) . ?
C1 C2 1.390(2) . ?
C1 C6 1.401(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C6 C7 1.444(2) . ?
C7 C8 1.391(2) . ?
C7 C12 1.412(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(2) . ?
C13 C14 1.384(2) . ?
C13 C18 1.407(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(2) . ?
C18 C19 1.442(3) . ?
C19 C20 1.400(2) . ?
C19 C24 1.402(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.373(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.398(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(3) . ?
C25 C26 1.391(2) . ?
C25 C30 1.401(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.384(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.389(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.382(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.393(2) . ?
C30 C31 1.448(2) . ?
C31 C32 1.391(2) . ?
C31 C36 1.408(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.381(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.393(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.385(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.395(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 P1 N3 100.56(6) . . ?
N2 P1 N1 103.84(6) . . ?
N2 P1 N3 103.16(7) . . ?
C1 N1 P1 116.17(10) . . ?
C1 N1 C12 107.18(12) . . ?
C12 N1 P1 134.45(10) . . ?
C13 N2 P1 134.37(11) . . ?
C13 N2 C24 107.23(13) . . ?
C24 N2 P1 117.85(11) . . ?
C25 N3 P1 116.06(10) . . ?
C25 N3 C36 106.84(12) . . ?
C36 N3 P1 134.48(10) . . ?
C2 C1 N1 128.23(14) . . ?
C2 C1 C6 122.07(14) . . ?
C6 C1 N1 109.70(13) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.03(16) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.66(17) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.65(16) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.01(17) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.96(13) . . ?
C5 C6 C1 119.59(15) . . ?
C5 C6 C7 133.44(16) . . ?
C8 C7 C6 132.62(15) . . ?
C8 C7 C12 119.91(15) . . ?
C12 C7 C6 107.47(13) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.19(16) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.29(16) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.05(16) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 121.2 . . ?
C10 C11 C12 117.58(15) . . ?
C12 C11 H11 121.2 . . ?
C7 C12 N1 108.65(13) . . ?
C11 C12 N1 130.39(14) . . ?
C11 C12 C7 120.94(14) . . ?
C14 C13 N2 129.72(14) . . ?
C14 C13 C18 121.28(15) . . ?
C18 C13 N2 108.97(14) . . ?
C13 C14 H14 121.2 . . ?
C13 C14 C15 117.61(16) . . ?
C15 C14 H14 121.2 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.52(17) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.65(17) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.92(17) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C19 107.46(14) . . ?
C17 C18 C13 120.01(17) . . ?
C17 C18 C19 132.47(17) . . ?
C20 C19 C18 133.01(17) . . ?
C20 C19 C24 119.74(17) . . ?
C24 C19 C18 107.24(15) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.57(18) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 120.90(19) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.5(2) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 H23 121.3 . . ?
C22 C23 C24 117.48(18) . . ?
C24 C23 H23 121.3 . . ?
C19 C24 N2 109.08(14) . . ?
C23 C24 N2 129.11(16) . . ?
C23 C24 C19 121.75(16) . . ?
C26 C25 N3 128.55(15) . . ?
C26 C25 C30 121.53(14) . . ?
C30 C25 N3 109.90(13) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 C25 117.59(16) . . ?
C27 C26 H26 121.2 . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.48(16) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.84(16) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 120.6 . . ?
C28 C29 C30 118.73(16) . . ?
C30 C29 H29 120.6 . . ?
C25 C30 C31 106.79(13) . . ?
C29 C30 C25 119.78(15) . . ?
C29 C30 C31 133.41(15) . . ?
C32 C31 C30 132.15(15) . . ?
C32 C31 C36 120.39(15) . . ?
C36 C31 C30 107.39(13) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 C31 118.92(16) . . ?
C33 C32 H32 120.5 . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.29(16) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 119.0 . . ?
C35 C34 C33 122.03(16) . . ?
C35 C34 H34 119.0 . . ?
C34 C35 H35 121.2 . . ?
C34 C35 C36 117.63(15) . . ?
C36 C35 H35 121.2 . . ?
C31 C36 N3 109.06(13) . . ?
C35 C36 N3 130.28(14) . . ?
C35 C36 C31 120.66(14) . . ?

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
P1 N1 C1 C2 -12.8(2) . . . . ?
P1 N1 C1 C6 167.04(10) . . . . ?
P1 N1 C12 C7 -163.72(12) . . . . ?
P1 N1 C12 C11 14.7(3) . . . . ?
P1 N2 C13 C14 12.2(3) . . . . ?
P1 N2 C13 C18 -169.73(12) . . . . ?
P1 N2 C24 C19 171.28(11) . . . . ?
P1 N2 C24 C23 -11.5(2) . . . . ?
P1 N3 C25 C26 -12.4(2) . . . . ?
P1 N3 C25 C30 165.85(10) . . . . ?
P1 N3 C36 C31 -160.69(12) . . . . ?
P1 N3 C36 C35 19.3(3) . . . . ?
N1 P1 N2 C13 -79.18(15) . . . . ?
N1 P1 N2 C24 110.63(12) . . . . ?
N1 P1 N3 C25 -155.62(11) . . . . ?
N1 P1 N3 C36 3.16(16) . . . . ?
N1 C1 C2 C3 179.70(16) . . . . ?
N1 C1 C6 C5 -179.80(14) . . . . ?
N1 C1 C6 C7 -0.38(17) . . . . ?
N2 P1 N1 C1 -174.07(11) . . . . ?
N2 P1 N1 C12 -13.45(16) . . . . ?
N2 P1 N3 C25 97.31(12) . . . . ?
N2 P1 N3 C36 -103.91(15) . . . . ?
N2 C13 C14 C15 177.70(15) . . . . ?
N2 C13 C18 C17 -178.30(14) . . . . ?
N2 C13 C18 C19 -0.56(18) . . . . ?
N3 P1 N1 C1 79.41(12) . . . . ?
N3 P1 N1 C12 -119.98(15) . . . . ?
N3 P1 N2 C13 25.39(15) . . . . ?
N3 P1 N2 C24 -144.80(11) . . . . ?
N3 C25 C26 C27 178.86(15) . . . . ?
N3 C25 C30 C29 179.25(14) . . . . ?
N3 C25 C30 C31 -1.83(17) . . . . ?
C1 N1 C12 C7 -1.88(16) . . . . ?
C1 N1 C12 C11 176.49(16) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C6 C7 C8 -179.85(18) . . . . ?
C1 C6 C7 C12 -0.79(17) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C6 C7 179.45(15) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 -179.52(18) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C5 C6 C7 C12 178.52(18) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C7 C8 C9 177.42(18) . . . . ?
C6 C7 C12 N1 1.65(17) . . . . ?
C6 C7 C12 C11 -176.90(14) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C7 C12 N1 -179.14(15) . . . . ?
C8 C7 C12 C11 2.3(2) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 N1 -179.40(15) . . . . ?
C10 C11 C12 C7 -1.2(2) . . . . ?
C12 N1 C1 C2 -178.42(16) . . . . ?
C12 N1 C1 C6 1.40(17) . . . . ?
C12 C7 C8 C9 -1.5(3) . . . . ?
C13 N2 C24 C19 -1.39(17) . . . . ?
C13 N2 C24 C23 175.83(18) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C13 C18 C19 C20 -178.91(19) . . . . ?
C13 C18 C19 C24 -0.31(18) . . . . ?
C14 C13 C18 C17 0.0(2) . . . . ?
C14 C13 C18 C19 177.71(14) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C13 -0.2(3) . . . . ?
C16 C17 C18 C19 -177.25(18) . . . . ?
C17 C18 C19 C20 -1.6(3) . . . . ?
C17 C18 C19 C24 177.05(18) . . . . ?
C18 C13 C14 C15 -0.2(2) . . . . ?
C18 C19 C20 C21 177.0(2) . . . . ?
C18 C19 C24 N2 1.05(18) . . . . ?
C18 C19 C24 C23 -176.41(16) . . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
C20 C19 C24 N2 179.87(16) . . . . ?
C20 C19 C24 C23 2.4(3) . . . . ?
C20 C21 C22 C23 1.2(4) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 N2 -178.40(18) . . . . ?
C22 C23 C24 C19 -1.5(3) . . . . ?
C24 N2 C13 C14 -176.88(16) . . . . ?
C24 N2 C13 C18 1.20(17) . . . . ?
C24 C19 C20 C21 -1.5(3) . . . . ?
C25 N3 C36 C31 -0.55(16) . . . . ?
C25 N3 C36 C35 179.45(15) . . . . ?
C25 C26 C27 C28 1.1(3) . . . . ?
C25 C30 C31 C32 -175.58(17) . . . . ?
C25 C30 C31 C36 1.46(17) . . . . ?
C26 C25 C30 C29 -2.3(2) . . . . ?
C26 C25 C30 C31 176.60(14) . . . . ?
C26 C27 C28 C29 -1.5(3) . . . . ?
C27 C28 C29 C30 -0.1(3) . . . . ?
C28 C29 C30 C25 2.0(2) . . . . ?
C28 C29 C30 C31 -176.62(17) . . . . ?
C29 C30 C31 C32 3.1(3) . . . . ?
C29 C30 C31 C36 -179.84(17) . . . . ?
C30 C25 C26 C27 0.8(2) . . . . ?
C30 C31 C32 C33 177.98(16) . . . . ?
C30 C31 C36 N3 -0.56(17) . . . . ?
C30 C31 C36 C35 179.44(14) . . . . ?
C31 C32 C33 C34 0.9(3) . . . . ?
C32 C31 C36 N3 176.90(14) . . . . ?
C32 C31 C36 C35 -3.1(2) . . . . ?
C32 C33 C34 C35 -1.4(3) . . . . ?
C33 C34 C35 C36 -0.4(3) . . . . ?
C34 C35 C36 N3 -177.37(15) . . . . ?
C34 C35 C36 C31 2.6(2) . . . . ?
C36 N3 C25 C26 -176.79(15) . . . . ?
C36 N3 C25 C30 1.50(16) . . . . ?
C36 C31 C32 C33 1.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7264(14)
2 0.2736(14)

_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_m20170527b1
_database_code_depnum_ccdc_archive 'CCDC 1554055'
_audit_update_record             
;
2017-06-03 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;
_audit_creation_date             2017-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        DCPPO
_chemical_formula_moiety         'C30 H21 N2 O P'
_chemical_formula_sum            'C30 H21 N2 O P'
_chemical_formula_weight         456.46
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7137(11)
_cell_length_b                   16.0797(15)
_cell_length_c                   16.7860(19)
_cell_angle_alpha                118.304(8)
_cell_angle_beta                 102.154(14)
_cell_angle_gamma                94.713(11)
_cell_volume                     2205.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4582
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28428
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_min         3.082
_diffrn_ambient_temperature      133.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7963
_reflns_number_total             9993
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         9993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.8503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0976
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28), C(H), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C44(H44), C45(H45), C46(H46),
  C47(H47), C50(H50), C51(H51), C52(H52), C53(H53), C56(H56), C57(H57),
 C58(H58), C59(H59)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.14155(4) 0.34554(3) 0.10943(3) 0.01840(9) Uani 1 1 d . . . . .
P2 P 0.02658(4) 0.70277(3) 0.48275(3) 0.01942(9) Uani 1 1 d . . . . .
O1 O 0.01209(12) 0.34478(8) 0.14089(8) 0.0247(2) Uani 1 1 d . . . . .
O2 O 0.03703(12) 0.63537(8) 0.38854(8) 0.0285(3) Uani 1 1 d . . . . .
N1 N 0.11569(13) 0.36477(9) 0.01777(9) 0.0193(3) Uani 1 1 d . . . . .
N2 N 0.18502(13) 0.23560(9) 0.06626(9) 0.0186(3) Uani 1 1 d . . . . .
N3 N -0.01636(13) 0.80501(9) 0.49038(9) 0.0194(3) Uani 1 1 d . . . . .
N4 N 0.18551(13) 0.74319(9) 0.56593(9) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.29408(16) 0.43183(11) 0.20077(10) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.43495(18) 0.41822(12) 0.20639(11) 0.0271(4) Uani 1 1 d . . . . .
H2 H 0.452945 0.359906 0.160442 0.032 Uiso 1 1 calc R . . . .
C3 C 0.54831(19) 0.48927(13) 0.27854(12) 0.0326(4) Uani 1 1 d . . . . .
H3 H 0.644218 0.479849 0.282249 0.039 Uiso 1 1 calc R . . . .
C4 C 0.5222(2) 0.57430(13) 0.34552(12) 0.0320(4) Uani 1 1 d . . . . .
H4 H 0.600578 0.623993 0.394003 0.038 Uiso 1 1 calc R . . . .
C5 C 0.3828(2) 0.58710(12) 0.34209(12) 0.0319(4) Uani 1 1 d . . . . .
H5 H 0.365447 0.644883 0.389243 0.038 Uiso 1 1 calc R . . . .
C6 C 0.26795(18) 0.51619(11) 0.27030(11) 0.0255(3) Uani 1 1 d . . . . .
H6 H 0.172018 0.524930 0.268423 0.031 Uiso 1 1 calc R . . . .
C7 C 0.18654(16) 0.43655(11) 0.00406(11) 0.0197(3) Uani 1 1 d . . . . .
C8 C 0.31261(17) 0.50633(12) 0.05871(12) 0.0256(3) Uani 1 1 d . . . . .
H8 H 0.367403 0.512672 0.116054 0.031 Uiso 1 1 calc R . . . .
C9 C 0.35577(18) 0.56644(12) 0.02667(13) 0.0297(4) Uani 1 1 d . . . . .
H9 H 0.442091 0.614422 0.062984 0.036 Uiso 1 1 calc R . . . .
C10 C 0.27718(19) 0.55901(12) -0.05676(13) 0.0303(4) Uani 1 1 d . . . . .
H10 H 0.309378 0.602035 -0.076117 0.036 Uiso 1 1 calc R . . . .
C11 C 0.15267(18) 0.48922(12) -0.11129(12) 0.0263(3) Uani 1 1 d . . . . .
H11 H 0.098460 0.483452 -0.168494 0.032 Uiso 1 1 calc R . . . .
C12 C 0.10745(16) 0.42714(11) -0.08112(11) 0.0208(3) Uani 1 1 d . . . . .
C13 C -0.01610(16) 0.34870(11) -0.12179(11) 0.0210(3) Uani 1 1 d . . . . .
C14 C -0.12979(18) 0.30868(12) -0.20413(12) 0.0268(3) Uani 1 1 d . . . . .
H14 H -0.134581 0.332648 -0.246405 0.032 Uiso 1 1 calc R . . . .
C15 C -0.23527(18) 0.23359(13) -0.22313(12) 0.0293(4) Uani 1 1 d . . . . .
H15 H -0.314119 0.206035 -0.278592 0.035 Uiso 1 1 calc R . . . .
C16 C -0.22694(17) 0.19790(12) -0.16152(12) 0.0273(4) Uani 1 1 d . . . . .
H16 H -0.300006 0.145501 -0.176505 0.033 Uiso 1 1 calc R . . . .
C17 C -0.11529(17) 0.23651(11) -0.07902(11) 0.0240(3) Uani 1 1 d . . . . .
H17 H -0.111065 0.212325 -0.036943 0.029 Uiso 1 1 calc R . . . .
C18 C -0.00978(16) 0.31220(11) -0.06061(11) 0.0201(3) Uani 1 1 d . . . . .
C19 C 0.14639(16) 0.16775(11) 0.09390(10) 0.0185(3) Uani 1 1 d . . . . .
C20 C 0.06530(17) 0.17385(12) 0.15482(11) 0.0231(3) Uani 1 1 d . . . . .
H20 H 0.025184 0.228741 0.184891 0.028 Uiso 1 1 calc R . . . .
C21 C 0.04529(18) 0.09689(12) 0.16997(11) 0.0266(3) Uani 1 1 d . . . . .
H21 H -0.009521 0.099467 0.211452 0.032 Uiso 1 1 calc R . . . .
C22 C 0.10303(18) 0.01567(12) 0.12626(12) 0.0265(3) Uani 1 1 d . . . . .
H22 H 0.087267 -0.035890 0.138287 0.032 Uiso 1 1 calc R . . . .
C23 C 0.18319(17) 0.00989(11) 0.06545(11) 0.0238(3) Uani 1 1 d . . . . .
H23 H 0.222408 -0.045410 0.035214 0.029 Uiso 1 1 calc R . . . .
C24 C 0.20531(15) 0.08670(11) 0.04940(10) 0.0187(3) Uani 1 1 d . . . . .
C25 C 0.28716(15) 0.10510(11) -0.00549(10) 0.0187(3) Uani 1 1 d . . . . .
C26 C 0.37253(17) 0.05220(12) -0.05994(11) 0.0236(3) Uani 1 1 d . . . . .
H26 H 0.377526 -0.011040 -0.071139 0.028 Uiso 1 1 calc R . . . .
C27 C 0.44978(17) 0.09360(12) -0.09733(11) 0.0255(3) Uani 1 1 d . . . . .
H27 H 0.509501 0.058867 -0.133846 0.031 Uiso 1 1 calc R . . . .
C28 C 0.44073(17) 0.18569(12) -0.08191(11) 0.0241(3) Uani 1 1 d . . . . .
H28 H 0.496634 0.213443 -0.106853 0.029 Uiso 1 1 calc R . . . .
C C 0.35216(17) 0.23807(11) -0.03103(10) 0.0214(3) Uani 1 1 d . . . . .
H H 0.344296 0.300058 -0.022594 0.026 Uiso 1 1 calc R . . . .
C30 C 0.27530(16) 0.19683(11) 0.00720(10) 0.0186(3) Uani 1 1 d . . . . .
C31 C -0.10538(16) 0.65543(11) 0.51859(11) 0.0205(3) Uani 1 1 d . . . . .
C32 C -0.17500(17) 0.71526(12) 0.58182(11) 0.0236(3) Uani 1 1 d . . . . .
H32 H -0.151800 0.783200 0.607446 0.028 Uiso 1 1 calc R . . . .
C33 C -0.27787(18) 0.67559(13) 0.60723(12) 0.0283(4) Uani 1 1 d . . . . .
H33 H -0.325202 0.716328 0.650237 0.034 Uiso 1 1 calc R . . . .
C34 C -0.31161(18) 0.57673(13) 0.56996(13) 0.0304(4) Uani 1 1 d . . . . .
H34 H -0.381068 0.549808 0.588266 0.037 Uiso 1 1 calc R . . . .
C35 C -0.24478(19) 0.51672(13) 0.50612(13) 0.0322(4) Uani 1 1 d . . . . .
H35 H -0.269126 0.448788 0.480352 0.039 Uiso 1 1 calc R . . . .
C36 C -0.14243(17) 0.55553(12) 0.47972(12) 0.0267(3) Uani 1 1 d . . . . .
H36 H -0.097561 0.514228 0.435257 0.032 Uiso 1 1 calc R . . . .
C37 C -0.13184(16) 0.80007(12) 0.41857(11) 0.0212(3) Uani 1 1 d . . . . .
C38 C -0.19538(18) 0.72418(13) 0.32707(12) 0.0286(4) Uani 1 1 d . . . . .
H38 H -0.163477 0.664950 0.303280 0.034 Uiso 1 1 calc R . . . .
C39 C -0.30799(19) 0.73899(15) 0.27186(13) 0.0358(4) Uani 1 1 d . . . . .
H39 H -0.354881 0.688284 0.209204 0.043 Uiso 1 1 calc R . . . .
C40 C -0.35347(18) 0.82565(15) 0.30585(13) 0.0351(4) Uani 1 1 d . . . . .
H40 H -0.430832 0.833196 0.266243 0.042 Uiso 1 1 calc R . . . .
C41 C -0.28815(17) 0.90132(14) 0.39642(12) 0.0280(4) Uani 1 1 d . . . . .
H41 H -0.318796 0.960999 0.419173 0.034 Uiso 1 1 calc R . . . .
C42 C -0.17633(16) 0.88810(12) 0.45360(11) 0.0214(3) Uani 1 1 d . . . . .
C43 C -0.08875(15) 0.95041(11) 0.54983(11) 0.0196(3) Uani 1 1 d . . . . .
C44 C -0.08586(17) 1.04482(12) 0.61707(11) 0.0235(3) Uani 1 1 d . . . . .
H44 H -0.148908 1.080676 0.602002 0.028 Uiso 1 1 calc R . . . .
C45 C 0.00960(17) 1.08582(11) 0.70590(11) 0.0228(3) Uani 1 1 d . . . . .
H45 H 0.012213 1.150171 0.752446 0.027 Uiso 1 1 calc R . . . .
C46 C 0.10211(16) 1.03304(11) 0.72747(11) 0.0211(3) Uani 1 1 d . . . . .
H46 H 0.166511 1.061993 0.789154 0.025 Uiso 1 1 calc R . . . .
C47 C 0.10268(16) 0.93944(11) 0.66132(10) 0.0199(3) Uani 1 1 d . . . . .
H47 H 0.167040 0.904409 0.676684 0.024 Uiso 1 1 calc R . . . .
C48 C 0.00654(15) 0.89816(11) 0.57185(10) 0.0180(3) Uani 1 1 d . . . . .
C49 C 0.30434(16) 0.79713(11) 0.56145(11) 0.0204(3) Uani 1 1 d . . . . .
C50 C 0.31456(18) 0.81807(12) 0.49103(12) 0.0247(3) Uani 1 1 d . . . . .
H50 H 0.236662 0.794711 0.435715 0.030 Uiso 1 1 calc R . . . .
C51 C 0.44263(18) 0.87421(13) 0.50491(13) 0.0299(4) Uani 1 1 d . . . . .
H51 H 0.452974 0.889327 0.457923 0.036 Uiso 1 1 calc R . . . .
C52 C 0.55687(19) 0.90915(13) 0.58614(13) 0.0331(4) Uani 1 1 d . . . . .
H52 H 0.643161 0.948066 0.593824 0.040 Uiso 1 1 calc R . . . .
C53 C 0.54648(18) 0.88801(12) 0.65565(13) 0.0289(4) Uani 1 1 d . . . . .
H53 H 0.624736 0.911750 0.710853 0.035 Uiso 1 1 calc R . . . .
C54 C 0.41832(16) 0.83094(11) 0.64303(11) 0.0224(3) Uani 1 1 d . . . . .
C55 C 0.37185(16) 0.79648(11) 0.70026(11) 0.0209(3) Uani 1 1 d . . . . .
C56 C 0.44114(17) 0.80835(12) 0.78778(11) 0.0255(3) Uani 1 1 d . . . . .
H56 H 0.537078 0.844754 0.820426 0.031 Uiso 1 1 calc R . . . .
C57 C 0.36792(18) 0.76627(12) 0.82619(12) 0.0267(4) Uani 1 1 d . . . . .
H57 H 0.413112 0.775056 0.886423 0.032 Uiso 1 1 calc R . . . .
C58 C 0.22822(17) 0.71099(12) 0.77737(12) 0.0252(3) Uani 1 1 d . . . . .
H58 H 0.180662 0.681345 0.804358 0.030 Uiso 1 1 calc R . . . .
C59 C 0.15720(17) 0.69835(11) 0.69030(11) 0.0218(3) Uani 1 1 d . . . . .
H59 H 0.061941 0.660777 0.657526 0.026 Uiso 1 1 calc R . . . .
C60 C 0.22989(16) 0.74246(11) 0.65240(10) 0.0188(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
P1 O1 1.4641(11) . ?
P1 N1 1.6814(13) . ?
P1 N2 1.6927(13) . ?
P1 C1 1.7775(16) . ?
P2 O2 1.4650(12) . ?
P2 N3 1.6818(13) . ?
P2 N4 1.6799(13) . ?
P2 C31 1.7841(16) . ?
N1 C7 1.4307(19) . ?
N1 C18 1.425(2) . ?
N2 C19 1.4255(18) . ?
N2 C30 1.4179(18) . ?
N3 C37 1.4293(19) . ?
N3 C48 1.4276(19) . ?
N4 C49 1.4228(19) . ?
N4 C60 1.4305(19) . ?
C1 C2 1.394(2) . ?
C1 C6 1.395(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(2) . ?
C7 C12 1.404(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.377(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.395(2) . ?
C12 C13 1.445(2) . ?
C13 C14 1.393(2) . ?
C13 C18 1.398(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(2) . ?
C19 C20 1.390(2) . ?
C19 C24 1.401(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.394(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(2) . ?
C24 C25 1.448(2) . ?
C25 C26 1.394(2) . ?
C25 C30 1.405(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.383(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(2) . ?
C28 H28 0.9500 . ?
C28 C 1.388(2) . ?
C H 0.9500 . ?
C C30 1.390(2) . ?
C31 C32 1.396(2) . ?
C31 C36 1.396(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.385(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.382(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.384(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.386(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.389(2) . ?
C37 C42 1.398(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.392(2) . ?
C39 H39 0.9500 . ?
C39 C40 1.384(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.381(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.392(2) . ?
C42 C43 1.443(2) . ?
C43 C44 1.391(2) . ?
C43 C48 1.406(2) . ?
C44 H44 0.9500 . ?
C44 C45 1.379(2) . ?
C45 H45 0.9500 . ?
C45 C46 1.392(2) . ?
C46 H46 0.9500 . ?
C46 C47 1.385(2) . ?
C47 H47 0.9500 . ?
C47 C48 1.389(2) . ?
C49 C50 1.394(2) . ?
C49 C54 1.398(2) . ?
C50 H50 0.9500 . ?
C50 C51 1.382(2) . ?
C51 H51 0.9500 . ?
C51 C52 1.393(3) . ?
C52 H52 0.9500 . ?
C52 C53 1.381(3) . ?
C53 H53 0.9500 . ?
C53 C54 1.398(2) . ?
C54 C55 1.442(2) . ?
C55 C56 1.394(2) . ?
C55 C60 1.406(2) . ?
C56 H56 0.9500 . ?
C56 C57 1.381(2) . ?
C57 H57 0.9500 . ?
C57 C58 1.395(2) . ?
C58 H58 0.9500 . ?
C58 C59 1.387(2) . ?
C59 H59 0.9500 . ?
C59 C60 1.393(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N1 112.31(7) . . ?
O1 P1 N2 110.66(6) . . ?
O1 P1 C1 113.15(7) . . ?
N1 P1 N2 103.61(6) . . ?
N1 P1 C1 108.79(7) . . ?
N2 P1 C1 107.79(7) . . ?
O2 P2 N3 111.93(7) . . ?
O2 P2 N4 112.32(7) . . ?
O2 P2 C31 114.06(7) . . ?
N3 P2 C31 106.02(7) . . ?
N4 P2 N3 102.88(6) . . ?
N4 P2 C31 108.86(7) . . ?
C7 N1 P1 132.69(11) . . ?
C18 N1 P1 119.89(10) . . ?
C18 N1 C7 106.78(12) . . ?
C19 N2 P1 123.53(10) . . ?
C30 N2 P1 129.19(10) . . ?
C30 N2 C19 106.94(12) . . ?
C37 N3 P2 119.97(10) . . ?
C48 N3 P2 129.37(10) . . ?
C48 N3 C37 106.82(12) . . ?
C49 N4 P2 120.23(10) . . ?
C49 N4 C60 106.98(12) . . ?
C60 N4 P2 132.55(11) . . ?
C2 C1 P1 123.43(12) . . ?
C2 C1 C6 119.64(15) . . ?
C6 C1 P1 116.93(12) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.14(15) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.98(16) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.21(16) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.38(16) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.58(16) . . ?
C5 C6 H6 120.2 . . ?
C8 C7 N1 130.68(14) . . ?
C8 C7 C12 120.64(14) . . ?
C12 C7 N1 108.67(13) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 C7 117.64(15) . . ?
C9 C8 H8 121.2 . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.34(16) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.95(15) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.90(15) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C13 107.77(13) . . ?
C11 C12 C7 120.52(15) . . ?
C11 C12 C13 131.71(15) . . ?
C14 C13 C12 132.50(15) . . ?
C14 C13 C18 120.02(15) . . ?
C18 C13 C12 107.47(13) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.75(15) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.44(16) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 122.01(16) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 121.5 . . ?
C16 C17 C18 117.00(15) . . ?
C18 C17 H17 121.5 . . ?
C13 C18 N1 109.30(13) . . ?
C17 C18 N1 128.93(14) . . ?
C17 C18 C13 121.77(15) . . ?
C20 C19 N2 129.50(14) . . ?
C20 C19 C24 121.29(14) . . ?
C24 C19 N2 109.21(13) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 C19 117.42(15) . . ?
C21 C20 H20 121.3 . . ?
C20 C21 H21 119.0 . . ?
C20 C21 C22 122.06(15) . . ?
C22 C21 H21 119.0 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.24(15) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.6 . . ?
C22 C23 C24 118.73(15) . . ?
C24 C23 H23 120.6 . . ?
C19 C24 C25 107.21(13) . . ?
C23 C24 C19 120.25(14) . . ?
C23 C24 C25 132.50(14) . . ?
C26 C25 C24 132.18(14) . . ?
C26 C25 C30 120.27(14) . . ?
C30 C25 C24 107.49(13) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 C25 118.70(15) . . ?
C27 C26 H26 120.6 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.53(15) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.1 . . ?
C C28 C27 121.71(15) . . ?
C C28 H28 119.1 . . ?
C28 C H 121.1 . . ?
C28 C C30 117.78(14) . . ?
C30 C H 121.1 . . ?
C25 C30 N2 109.07(13) . . ?
C C30 N2 129.89(14) . . ?
C C30 C25 120.93(14) . . ?
C32 C31 P2 121.80(12) . . ?
C36 C31 P2 118.60(12) . . ?
C36 C31 C32 119.57(15) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.05(15) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 119.98(16) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 119.8 . . ?
C33 C34 C35 120.39(16) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 119.9 . . ?
C34 C35 C36 120.13(16) . . ?
C36 C35 H35 119.9 . . ?
C31 C36 H36 120.1 . . ?
C35 C36 C31 119.86(16) . . ?
C35 C36 H36 120.1 . . ?
C38 C37 N3 129.01(15) . . ?
C38 C37 C42 121.96(14) . . ?
C42 C37 N3 109.04(13) . . ?
C37 C38 H38 121.6 . . ?
C37 C38 C39 116.86(17) . . ?
C39 C38 H38 121.6 . . ?
C38 C39 H39 119.1 . . ?
C40 C39 C38 121.74(17) . . ?
C40 C39 H39 119.1 . . ?
C39 C40 H40 119.5 . . ?
C41 C40 C39 121.04(16) . . ?
C41 C40 H40 119.5 . . ?
C40 C41 H41 120.8 . . ?
C40 C41 C42 118.44(17) . . ?
C42 C41 H41 120.8 . . ?
C37 C42 C43 107.75(13) . . ?
C41 C42 C37 119.95(15) . . ?
C41 C42 C43 132.30(16) . . ?
C44 C43 C42 132.22(14) . . ?
C44 C43 C48 120.22(14) . . ?
C48 C43 C42 107.55(13) . . ?
C43 C44 H44 120.4 . . ?
C45 C44 C43 119.25(14) . . ?
C45 C44 H44 120.4 . . ?
C44 C45 H45 119.9 . . ?
C44 C45 C46 120.12(15) . . ?
C46 C45 H45 119.9 . . ?
C45 C46 H46 119.2 . . ?
C47 C46 C45 121.70(15) . . ?
C47 C46 H46 119.2 . . ?
C46 C47 H47 120.9 . . ?
C46 C47 C48 118.18(14) . . ?
C48 C47 H47 120.9 . . ?
C43 C48 N3 108.81(13) . . ?
C47 C48 N3 130.67(13) . . ?
C47 C48 C43 120.53(14) . . ?
C50 C49 N4 128.85(14) . . ?
C50 C49 C54 121.85(14) . . ?
C54 C49 N4 109.30(13) . . ?
C49 C50 H50 121.3 . . ?
C51 C50 C49 117.31(16) . . ?
C51 C50 H50 121.3 . . ?
C50 C51 H51 119.2 . . ?
C50 C51 C52 121.59(16) . . ?
C52 C51 H51 119.2 . . ?
C51 C52 H52 119.5 . . ?
C53 C52 C51 120.93(16) . . ?
C53 C52 H52 119.5 . . ?
C52 C53 H53 120.7 . . ?
C52 C53 C54 118.56(16) . . ?
C54 C53 H53 120.7 . . ?
C49 C54 C53 119.76(15) . . ?
C49 C54 C55 107.42(13) . . ?
C53 C54 C55 132.82(15) . . ?
C56 C55 C54 131.86(15) . . ?
C56 C55 C60 120.21(15) . . ?
C60 C55 C54 107.92(13) . . ?
C55 C56 H56 120.6 . . ?
C57 C56 C55 118.86(15) . . ?
C57 C56 H56 120.6 . . ?
C56 C57 H57 119.7 . . ?
C56 C57 C58 120.62(15) . . ?
C58 C57 H57 119.7 . . ?
C57 C58 H58 119.3 . . ?
C59 C58 C57 121.46(15) . . ?
C59 C58 H58 119.3 . . ?
C58 C59 H59 121.0 . . ?
C58 C59 C60 117.95(15) . . ?
C60 C59 H59 121.0 . . ?
C55 C60 N4 108.36(13) . . ?
C59 C60 N4 130.77(14) . . ?
C59 C60 C55 120.86(14) . . ?

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
P1 N1 C7 C8 9.7(3) . . . . ?
P1 N1 C7 C12 -171.32(11) . . . . ?
P1 N1 C18 C13 172.84(10) . . . . ?
P1 N1 C18 C17 -6.7(2) . . . . ?
P1 N2 C19 C20 2.8(2) . . . . ?
P1 N2 C19 C24 -176.71(10) . . . . ?
P1 N2 C30 C25 176.18(11) . . . . ?
P1 N2 C30 C 0.0(2) . . . . ?
P1 C1 C2 C3 178.86(13) . . . . ?
P1 C1 C6 C5 -178.50(13) . . . . ?
P2 N3 C37 C38 -19.2(2) . . . . ?
P2 N3 C37 C42 161.44(10) . . . . ?
P2 N3 C48 C43 -159.38(11) . . . . ?
P2 N3 C48 C47 20.9(2) . . . . ?
P2 N4 C49 C50 -5.2(2) . . . . ?
P2 N4 C49 C54 173.78(10) . . . . ?
P2 N4 C60 C55 -173.05(11) . . . . ?
P2 N4 C60 C59 7.6(2) . . . . ?
P2 C31 C32 C33 179.39(12) . . . . ?
P2 C31 C36 C35 -179.88(13) . . . . ?
O1 P1 N1 C7 122.71(14) . . . . ?
O1 P1 N1 C18 -46.81(13) . . . . ?
O1 P1 N2 C19 -25.90(14) . . . . ?
O1 P1 N2 C30 161.66(12) . . . . ?
O1 P1 C1 C2 147.38(13) . . . . ?
O1 P1 C1 C6 -31.56(14) . . . . ?
O2 P2 N3 C37 47.21(13) . . . . ?
O2 P2 N3 C48 -157.94(12) . . . . ?
O2 P2 N4 C49 61.78(13) . . . . ?
O2 P2 N4 C60 -124.68(14) . . . . ?
O2 P2 C31 C32 -151.83(12) . . . . ?
O2 P2 C31 C36 26.18(15) . . . . ?
N1 P1 N2 C19 -146.49(12) . . . . ?
N1 P1 N2 C30 41.07(14) . . . . ?
N1 P1 C1 C2 -87.06(14) . . . . ?
N1 P1 C1 C6 94.00(13) . . . . ?
N1 C7 C8 C9 179.62(15) . . . . ?
N1 C7 C12 C11 179.53(13) . . . . ?
N1 C7 C12 C13 0.45(16) . . . . ?
N2 P1 N1 C7 -117.82(14) . . . . ?
N2 P1 N1 C18 72.65(12) . . . . ?
N2 P1 C1 C2 24.67(15) . . . . ?
N2 P1 C1 C6 -154.27(11) . . . . ?
N2 C19 C20 C21 -179.36(14) . . . . ?
N2 C19 C24 C23 179.72(13) . . . . ?
N2 C19 C24 C25 1.82(16) . . . . ?
N3 P2 N4 C49 -58.75(12) . . . . ?
N3 P2 N4 C60 114.78(14) . . . . ?
N3 P2 C31 C32 -28.20(14) . . . . ?
N3 P2 C31 C36 149.81(12) . . . . ?
N3 C37 C38 C39 179.51(15) . . . . ?
N3 C37 C42 C41 179.88(13) . . . . ?
N3 C37 C42 C43 -0.48(16) . . . . ?
N4 P2 N3 C37 168.01(11) . . . . ?
N4 P2 N3 C48 -37.14(14) . . . . ?
N4 P2 C31 C32 81.87(14) . . . . ?
N4 P2 C31 C36 -100.12(13) . . . . ?
N4 C49 C50 C51 178.69(15) . . . . ?
N4 C49 C54 C53 -178.56(14) . . . . ?
N4 C49 C54 C55 0.89(17) . . . . ?
C1 P1 N1 C7 -3.33(16) . . . . ?
C1 P1 N1 C18 -172.86(11) . . . . ?
C1 P1 N2 C19 98.31(12) . . . . ?
C1 P1 N2 C30 -74.13(14) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C1 C6 C5 2.5(2) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C6 C1 C2 C3 -2.2(2) . . . . ?
C7 N1 C18 C13 0.86(16) . . . . ?
C7 N1 C18 C17 -178.69(15) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C7 C12 C13 C14 179.46(16) . . . . ?
C7 C12 C13 C18 0.09(17) . . . . ?
C8 C7 C12 C11 -1.4(2) . . . . ?
C8 C7 C12 C13 179.52(14) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C7 0.9(2) . . . . ?
C10 C11 C12 C13 179.70(16) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C11 C12 C13 C18 -178.85(16) . . . . ?
C12 C7 C8 C9 0.8(2) . . . . ?
C12 C13 C14 C15 -178.78(16) . . . . ?
C12 C13 C18 N1 -0.59(16) . . . . ?
C12 C13 C18 C17 179.00(14) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C13 C18 N1 179.94(13) . . . . ?
C14 C13 C18 C17 -0.5(2) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C16 C17 C18 N1 -179.89(14) . . . . ?
C16 C17 C18 C13 0.6(2) . . . . ?
C18 N1 C7 C8 -179.75(16) . . . . ?
C18 N1 C7 C12 -0.80(16) . . . . ?
C18 C13 C14 C15 0.5(2) . . . . ?
C19 N2 C30 C25 2.76(16) . . . . ?
C19 N2 C30 C -173.38(15) . . . . ?
C19 C20 C21 C22 -0.2(2) . . . . ?
C19 C24 C25 C26 176.78(16) . . . . ?
C19 C24 C25 C30 -0.10(16) . . . . ?
C20 C19 C24 C23 0.1(2) . . . . ?
C20 C19 C24 C25 -177.77(13) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C21 C22 C23 C24 0.3(2) . . . . ?
C22 C23 C24 C19 -0.4(2) . . . . ?
C22 C23 C24 C25 176.93(15) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C23 C24 C25 C30 -177.64(15) . . . . ?
C24 C19 C20 C21 0.1(2) . . . . ?
C24 C25 C26 C27 -173.68(15) . . . . ?
C24 C25 C30 N2 -1.67(16) . . . . ?
C24 C25 C30 C 174.88(13) . . . . ?
C25 C26 C27 C28 -0.9(2) . . . . ?
C26 C25 C30 N2 -178.99(13) . . . . ?
C26 C25 C30 C -2.4(2) . . . . ?
C26 C27 C28 C -1.6(2) . . . . ?
C27 C28 C C30 2.1(2) . . . . ?
C28 C C30 N2 175.71(14) . . . . ?
C28 C C30 C25 0.0(2) . . . . ?
C30 N2 C19 C20 176.71(15) . . . . ?
C30 N2 C19 C24 -2.83(16) . . . . ?
C30 C25 C26 C27 2.9(2) . . . . ?
C31 P2 N3 C37 -77.75(12) . . . . ?
C31 P2 N3 C48 77.10(14) . . . . ?
C31 P2 N4 C49 -170.92(11) . . . . ?
C31 P2 N4 C60 2.61(16) . . . . ?
C31 C32 C33 C34 0.0(2) . . . . ?
C32 C31 C36 C35 -1.8(2) . . . . ?
C32 C33 C34 C35 -1.0(3) . . . . ?
C33 C34 C35 C36 0.6(3) . . . . ?
C34 C35 C36 C31 0.9(3) . . . . ?
C36 C31 C32 C33 1.4(2) . . . . ?
C37 N3 C48 C43 -2.00(16) . . . . ?
C37 N3 C48 C47 178.32(15) . . . . ?
C37 C38 C39 C40 0.9(3) . . . . ?
C37 C42 C43 C44 179.54(16) . . . . ?
C37 C42 C43 C48 -0.77(16) . . . . ?
C38 C37 C42 C41 0.5(2) . . . . ?
C38 C37 C42 C43 -179.90(14) . . . . ?
C38 C39 C40 C41 0.1(3) . . . . ?
C39 C40 C41 C42 -0.9(2) . . . . ?
C40 C41 C42 C37 0.6(2) . . . . ?
C40 C41 C42 C43 -178.94(16) . . . . ?
C41 C42 C43 C44 -0.9(3) . . . . ?
C41 C42 C43 C48 178.81(16) . . . . ?
C42 C37 C38 C39 -1.2(2) . . . . ?
C42 C43 C44 C45 178.50(15) . . . . ?
C42 C43 C48 N3 1.72(16) . . . . ?
C42 C43 C48 C47 -178.56(13) . . . . ?
C43 C44 C45 C46 0.2(2) . . . . ?
C44 C43 C48 N3 -178.54(13) . . . . ?
C44 C43 C48 C47 1.2(2) . . . . ?
C44 C45 C46 C47 0.7(2) . . . . ?
C45 C46 C47 C48 -0.7(2) . . . . ?
C46 C47 C48 N3 179.40(14) . . . . ?
C46 C47 C48 C43 -0.3(2) . . . . ?
C48 N3 C37 C38 -179.12(15) . . . . ?
C48 N3 C37 C42 1.52(16) . . . . ?
C48 C43 C44 C45 -1.2(2) . . . . ?
C49 N4 C60 C55 1.11(16) . . . . ?
C49 N4 C60 C59 -178.20(15) . . . . ?
C49 C50 C51 C52 -0.4(2) . . . . ?
C49 C54 C55 C56 179.98(16) . . . . ?
C49 C54 C55 C60 -0.19(17) . . . . ?
C50 C49 C54 C53 0.5(2) . . . . ?
C50 C49 C54 C55 179.92(14) . . . . ?
C50 C51 C52 C53 0.6(3) . . . . ?
C51 C52 C53 C54 -0.2(3) . . . . ?
C52 C53 C54 C49 -0.3(2) . . . . ?
C52 C53 C54 C55 -179.56(17) . . . . ?
C53 C54 C55 C56 -0.7(3) . . . . ?
C53 C54 C55 C60 179.17(17) . . . . ?
C54 C49 C50 C51 -0.1(2) . . . . ?
C54 C55 C56 C57 179.78(16) . . . . ?
C54 C55 C60 N4 -0.58(16) . . . . ?
C54 C55 C60 C59 178.82(13) . . . . ?
C55 C56 C57 C58 1.4(2) . . . . ?
C56 C55 C60 N4 179.27(13) . . . . ?
C56 C55 C60 C59 -1.3(2) . . . . ?
C56 C57 C58 C59 -1.6(2) . . . . ?
C57 C58 C59 C60 0.2(2) . . . . ?
C58 C59 C60 N4 -179.53(14) . . . . ?
C58 C59 C60 C55 1.2(2) . . . . ?
C60 N4 C49 C50 179.82(15) . . . . ?
C60 N4 C49 C54 -1.25(16) . . . . ?
C60 C55 C56 C57 0.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_TCPO
_database_code_depnum_ccdc_archive 'CCDC 1554057'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;
_audit_creation_date             2017-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        'tri(9H-carbazol-9-yl)phosphine oxide'
_chemical_formula_moiety         'C36 H24 N3 O P'
_chemical_formula_sum            'C36 H24 N3 O P'
_chemical_formula_weight         545.59
_chemical_oxdiff_formula         'C36 H24 N3 P O'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.10434 0.09671 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   16.8479(5)
_cell_length_b                   8.9589(2)
_cell_length_c                   18.2273(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.540(3)
_cell_angle_gamma                90
_cell_volume                     2685.57(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20321
_cell_measurement_temperature    180.0(3)
_cell_measurement_theta_max      30.1740
_cell_measurement_theta_min      3.9300
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3493
_exptl_crystal_description       block
_exptl_crystal_F_000             1136.8518
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 8 18 0.1471
-6 -11 -10 0.0957
-7 -6 -19 0.1197
6 2 23 0.1204
1 -8 18 0.1145
-3 -12 7 0.1118
-14 -4 -15 0.1090
-10 3 -19 0.1443
-8 12 2 0.1243
9 11 3 0.1183
-1 4 -24 0.1577
7 -4 -24 0.1103
23 1 1 0.1130
21 -2 -15 0.1282
10 -11 -3 0.1024
3 -10 -15 0.1069
-24 -1 5 0.0666
-21 6 2 0.0989
-18 2 -11 0.1133
14 0 -24 0.1184
22 4 1 0.1143
22 -4 3 0.1167
-19 -7 5 0.0735
-15 1 23 0.0894

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.194
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.9236 7.9174 17.6743 -0.1644 -0.3292 -0.9299
-6.0049 -11.0171 -10.0106 0.1840 0.6675 0.7437
-7.0061 -6.0078 -19.0245 0.0334 0.2001 0.9756
6.0048 2.0008 23.0314 0.0374 0.1448 -1.0082
1.0004 -8.0152 18.0275 0.2001 0.8082 -0.4909
-3.0029 -12.0206 7.0134 0.2383 0.9596 0.0852
-14.0180 -4.0054 -15.0189 -0.3102 0.1965 0.9208
-10.0128 3.0068 -19.0268 -0.3666 -0.3856 0.8234
-8.0155 12.0190 2.0001 -0.6914 -0.7089 -0.1969
9.0107 11.0180 3.0005 -0.0368 -0.8041 -0.5468
-0.9984 4.0094 -24.0348 -0.0403 -0.6239 0.8047
7.0158 -4.0033 -24.0333 0.5121 -0.1593 0.8343
23.0349 1.0026 0.9993 0.8119 -0.2955 -0.5159
21.0353 -2.0005 -15.0222 0.9178 -0.3087 0.1803
10.0185 -11.0172 -3.0020 0.7383 0.6043 0.1704
3.0095 -10.0144 -15.0186 0.5103 0.4293 0.7250
-24.0375 -1.0033 5.0092 -0.8801 0.3960 0.3159
-21.0340 6.0086 2.0028 -0.9786 -0.1607 0.2018
-18.0263 2.0038 -11.0146 -0.6715 -0.1129 0.7125
14.0256 0.0035 -24.0349 0.6420 -0.5073 0.6015
22.0327 4.0074 0.9986 0.6786 -0.4907 -0.5666
22.0342 -4.0059 3.0036 0.9252 0.0880 -0.4517
-19.0284 -7.0129 5.0105 -0.5027 0.7549 0.3579
-15.0272 0.9982 23.0333 -0.7059 0.4342 -0.5686

_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            52870
_diffrn_reflns_theta_full        28.6995
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.63
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9908
_diffrn_measured_fraction_theta_max 0.9908
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  88.00   0.50    1.00    --   -1.70  57.00   0.00  186
  2  ω      3.00  29.00   0.50    1.00    --    1.90  57.00  90.00   52
  3  ω      4.00  90.00   0.50    1.00    --    1.90  57.00 120.00  172
  4  ω     52.00  78.00   0.50    1.00    --    1.90  57.00 -30.00   52
  5  ω     54.00  87.00   0.50    1.00    --    1.90  57.00 150.00   66
  6  ω    -19.00  86.00   0.50    1.00    --    1.90  57.00  60.00  210
  7  ω     37.00  83.00   0.50    1.00    --    1.90  57.00  90.00   92
  8  ω    -20.00  18.00   0.50    1.00    --    1.90  57.00 -30.00   76
  9  ω     66.00  91.00   0.50    1.00    --    1.90  57.00 -60.00   50
 10  ω    -20.00  11.00   0.50    1.00    --    1.90  57.00 -60.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0368675000
_diffrn_orient_matrix_UB_12      -0.0320706000
_diffrn_orient_matrix_UB_13      -0.0052035000
_diffrn_orient_matrix_UB_21      -0.0104962000
_diffrn_orient_matrix_UB_22      -0.0684716000
_diffrn_orient_matrix_UB_23      0.0149716000
_diffrn_orient_matrix_UB_31      -0.0197855000
_diffrn_orient_matrix_UB_32      -0.0234882000
_diffrn_orient_matrix_UB_33      -0.0365769000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                6182
_reflns_number_total             6883
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.3315
_refine_diff_density_min         -0.3725
_refine_diff_density_rms         0.0455
_refine_ls_d_res_high            0.7400
_refine_ls_d_res_low             5.6113
_refine_ls_goodness_of_fit_ref   1.0336
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6883
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.0336
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.9444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0938
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C35(H35), C14(H14), C2(H2), C11(H11), C15(H15), C26(H26), C17(H17), C27(H27),
 C23(H23), C22(H22), C20(H20), C3(H3), C9(H9), C5(H5), C28(H28), C32(H32),
 C34(H34), C21(H21), C29(H29), C10(H10), C33(H33), C4(H4), C8(H8), C16(H16)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
P1 P 0.214551(15) 0.16448(3) 0.180469(14) 0.01701(7) Uani 1.000000 .
O1 O 0.17703(5) 0.03666(8) 0.13591(5) 0.02591(17) Uani 1.000000 .
N2 N 0.26313(5) 0.27928(9) 0.13225(5) 0.01890(17) Uani 1.000000 .
N3 N 0.28625(5) 0.11289(9) 0.25501(5) 0.01889(17) Uani 1.000000 .
N1 N 0.14631(5) 0.26822(10) 0.21068(5) 0.01967(17) Uani 1.000000 .
C35 C 0.39422(7) 0.31789(13) 0.27081(6) 0.0275(2) Uani 1.000000 .
H35 H 0.35836(7) 0.39432(13) 0.24754(6) 0.0330(3) Uiso 1.000000 R
C13 C 0.25146(6) 0.43308(11) 0.11128(6) 0.02022(19) Uani 1.000000 .
C12 C 0.07391(6) 0.31601(12) 0.15906(6) 0.0220(2) Uani 1.000000 .
C36 C 0.36647(6) 0.17320(12) 0.27831(6) 0.0202(2) Uani 1.000000 .
C1 C 0.14404(6) 0.33049(11) 0.28250(6) 0.0204(2) Uani 1.000000 .
C19 C 0.33493(6) 0.32718(13) 0.04047(6) 0.0246(2) Uani 1.000000 .
C30 C 0.36977(7) -0.06989(12) 0.32056(6) 0.0247(2) Uani 1.000000 .
C25 C 0.28920(7) -0.03615(11) 0.28456(6) 0.0211(2) Uani 1.000000 .
C31 C 0.41845(6) 0.06184(13) 0.31636(6) 0.0236(2) Uani 1.000000 .
C14 C 0.20964(7) 0.54550(12) 0.13961(7) 0.0257(2) Uani 1.000000 .
H14 H 0.18369(7) 0.52714(12) 0.18008(7) 0.0309(3) Uiso 1.000000 R
C24 C 0.31586(6) 0.21722(12) 0.08876(5) 0.0210(2) Uani 1.000000 .
C2 C 0.19803(7) 0.31488(13) 0.35177(6) 0.0267(2) Uani 1.000000 .
H2 H 0.24660(7) 0.25834(13) 0.35668(6) 0.0320(3) Uiso 1.000000 R
C7 C 0.02885(6) 0.40754(12) 0.19731(7) 0.0255(2) Uani 1.000000 .
C6 C 0.07197(6) 0.41455(12) 0.27524(6) 0.0252(2) Uani 1.000000 .
C11 C 0.04856(7) 0.28473(14) 0.08260(7) 0.0286(2) Uani 1.000000 .
H11 H 0.07952(7) 0.22229(14) 0.05728(7) 0.0344(3) Uiso 1.000000 R
C15 C 0.20722(8) 0.68622(13) 0.10640(7) 0.0326(3) Uani 1.000000 .
H15 H 0.17869(8) 0.76464(13) 0.12451(7) 0.0392(3) Uiso 1.000000 R
C26 C 0.22584(8) -0.13628(13) 0.28297(7) 0.0283(2) Uani 1.000000 .
H26 H 0.17150(8) -0.11199(13) 0.25902(7) 0.0340(3) Uiso 1.000000 R
C18 C 0.29361(6) 0.46260(12) 0.05386(6) 0.0243(2) Uani 1.000000 .
C17 C 0.28996(8) 0.60447(14) 0.02117(7) 0.0332(3) Uani 1.000000 .
H17 H 0.31739(8) 0.62461(14) -0.01812(7) 0.0398(3) Uiso 1.000000 R
C27 C 0.24536(10) -0.27391(14) 0.31801(7) 0.0375(3) Uani 1.000000 .
H27 H 0.20323(10) -0.34399(14) 0.31878(7) 0.0450(4) Uiso 1.000000 R
C23 C 0.34534(7) 0.07172(13) 0.08930(6) 0.0270(2) Uani 1.000000 .
H23 H 0.33288(7) -0.00143(13) 0.12282(6) 0.0324(3) Uiso 1.000000 R
C22 C 0.39396(8) 0.03812(16) 0.03849(7) 0.0351(3) Uani 1.000000 .
H22 H 0.41425(8) -0.06047(16) 0.03681(7) 0.0421(3) Uiso 1.000000 R
C20 C 0.38491(7) 0.29134(17) -0.00909(7) 0.0343(3) Uani 1.000000 .
H20 H 0.39905(7) 0.36493(17) -0.04154(7) 0.0411(3) Uiso 1.000000 R
C3 C 0.17819(8) 0.38515(15) 0.41350(7) 0.0345(3) Uani 1.000000 .
H3 H 0.21431(8) 0.37678(15) 0.46121(7) 0.0413(3) Uiso 1.000000 R
C9 C -0.06918(8) 0.44259(17) 0.08173(9) 0.0414(3) Uani 1.000000 .
H9 H -0.11822(8) 0.48572(17) 0.05432(9) 0.0497(4) Uiso 1.000000 R
C5 C 0.05321(8) 0.48272(15) 0.33843(8) 0.0358(3) Uani 1.000000 .
H5 H 0.00447(8) 0.53855(15) 0.33409(8) 0.0430(3) Uiso 1.000000 R
C28 C 0.32538(10) -0.31108(14) 0.35199(7) 0.0421(3) Uani 1.000000 .
H28 H 0.33693(10) -0.40675(14) 0.37422(7) 0.0506(4) Uiso 1.000000 R
C32 C 0.50097(7) 0.09283(16) 0.34382(7) 0.0339(3) Uani 1.000000 .
H32 H 0.53671(7) 0.01800(16) 0.36899(7) 0.0407(3) Uiso 1.000000 R
C34 C 0.47666(8) 0.34601(16) 0.29879(7) 0.0355(3) Uani 1.000000 .
H34 H 0.49736(8) 0.44334(16) 0.29406(7) 0.0426(3) Uiso 1.000000 R
C21 C 0.41342(8) 0.14613(18) -0.00988(7) 0.0387(3) Uani 1.000000 .
H21 H 0.44665(8) 0.11990(18) -0.04385(7) 0.0465(4) Uiso 1.000000 R
C29 C 0.38803(9) -0.21058(14) 0.35374(7) 0.0362(3) Uani 1.000000 .
H29 H 0.44238(9) -0.23629(14) 0.37696(7) 0.0435(3) Uiso 1.000000 R
C10 C -0.02414(8) 0.34912(15) 0.04505(8) 0.0371(3) Uani 1.000000 .
H10 H -0.04358(8) 0.32887(15) -0.00691(8) 0.0445(3) Uiso 1.000000 R
C33 C 0.52953(7) 0.23419(18) 0.33366(7) 0.0388(3) Uani 1.000000 .
H33 H 0.58575(7) 0.25568(18) 0.35055(7) 0.0466(4) Uiso 1.000000 R
C4 C 0.10660(9) 0.46771(15) 0.40730(8) 0.0390(3) Uani 1.000000 .
H4 H 0.09458(9) 0.51368(15) 0.45059(8) 0.0467(4) Uiso 1.000000 R
C8 C -0.04332(7) 0.47334(15) 0.15762(8) 0.0358(3) Uani 1.000000 .
H8 H -0.07388(7) 0.53780(15) 0.18233(8) 0.0430(3) Uiso 1.000000 R
C16 C 0.24563(8) 0.71485(13) 0.04720(8) 0.0363(3) Uani 1.000000 .
H16 H 0.24128(8) 0.81092(13) 0.02462(8) 0.0436(3) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4655(8) . ?
P1 N2 1.6771(9) . ?
P1 N3 1.6751(9) . ?
P1 N1 1.6625(9) . ?
N2 C13 1.4320(12) . ?
N2 C24 1.4257(12) . ?
N3 C36 1.4317(13) . ?
N3 C25 1.4366(12) . ?
N1 C12 1.4346(13) . ?
N1 C1 1.4312(13) . ?
C35 C36 1.3948(15) . ?
C35 C34 1.3947(16) . ?
C13 C14 1.3911(15) . ?
C13 C18 1.4117(15) . ?
C12 C7 1.4016(15) . ?
C12 C11 1.3946(16) . ?
C36 C31 1.4069(14) . ?
C1 C2 1.3937(15) . ?
C1 C6 1.4103(14) . ?
C19 C24 1.4040(15) . ?
C19 C18 1.4456(16) . ?
C19 C20 1.3995(16) . ?
C30 C25 1.4064(15) . ?
C30 C31 1.4485(16) . ?
C30 C29 1.4029(15) . ?
C25 C26 1.3899(15) . ?
C31 C32 1.3995(16) . ?
C14 C15 1.3952(15) . ?
C24 C23 1.3942(15) . ?
C2 C3 1.3919(16) . ?
C7 C6 1.4496(16) . ?
C7 C8 1.4027(15) . ?
C6 C5 1.3992(16) . ?
C11 C10 1.3919(16) . ?
C15 C16 1.397(2) . ?
C26 C27 1.3947(16) . ?
C18 C17 1.3994(15) . ?
C17 C16 1.384(2) . ?
C27 C28 1.396(2) . ?
C23 C22 1.3959(16) . ?
C22 C21 1.395(2) . ?
C20 C21 1.388(2) . ?
C3 C4 1.3984(19) . ?
C9 C10 1.394(2) . ?
C9 C8 1.385(2) . ?
C5 C4 1.383(2) . ?
C28 C29 1.382(2) . ?
C32 C33 1.381(2) . ?
C34 C33 1.398(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 P1 O1 112.93(5) . . ?
N3 P1 O1 112.47(4) . . ?
N3 P1 N2 104.26(4) . . ?
N1 P1 O1 111.98(5) . . ?
N1 P1 N2 106.38(4) . . ?
N1 P1 N3 108.32(4) . . ?
C13 N2 P1 132.50(7) . . ?
C24 N2 P1 119.09(7) . . ?
C24 N2 C13 107.03(8) . . ?
C36 N3 P1 127.20(7) . . ?
C25 N3 P1 121.38(7) . . ?
C25 N3 C36 106.61(8) . . ?
C12 N1 P1 120.02(7) . . ?
C1 N1 P1 132.74(7) . . ?
C1 N1 C12 107.21(8) . . ?
C34 C35 C36 117.41(11) . . ?
C14 C13 N2 130.46(10) . . ?
C18 C13 N2 108.43(9) . . ?
C18 C13 C14 121.09(10) . . ?
C7 C12 N1 108.88(9) . . ?
C11 C12 N1 128.88(10) . . ?
C11 C12 C7 122.23(10) . . ?
C35 C36 N3 129.54(10) . . ?
C31 C36 N3 108.97(9) . . ?
C31 C36 C35 121.42(10) . . ?
C2 C1 N1 130.37(9) . . ?
C6 C1 N1 108.40(9) . . ?
C6 C1 C2 121.19(10) . . ?
C18 C19 C24 107.39(9) . . ?
C20 C19 C24 119.69(11) . . ?
C20 C19 C18 132.91(11) . . ?
C31 C30 C25 107.48(9) . . ?
C29 C30 C25 119.55(11) . . ?
C29 C30 C31 132.93(11) . . ?
C30 C25 N3 109.03(9) . . ?
C26 C25 N3 128.91(10) . . ?
C26 C25 C30 122.02(10) . . ?
C30 C31 C36 107.75(9) . . ?
C32 C31 C36 119.96(11) . . ?
C32 C31 C30 132.27(11) . . ?
C15 C14 C13 117.56(11) . . ?
C19 C24 N2 109.27(9) . . ?
C23 C24 N2 128.66(10) . . ?
C23 C24 C19 122.06(10) . . ?
C3 C2 C1 117.57(10) . . ?
C6 C7 C12 107.60(9) . . ?
C8 C7 C12 119.46(11) . . ?
C8 C7 C6 132.93(11) . . ?
C7 C6 C1 107.88(9) . . ?
C5 C6 C1 119.97(11) . . ?
C5 C6 C7 132.13(10) . . ?
C10 C11 C12 117.00(12) . . ?
C16 C15 C14 121.74(12) . . ?
C27 C26 C25 117.22(12) . . ?
C19 C18 C13 107.83(9) . . ?
C17 C18 C13 120.21(11) . . ?
C17 C18 C19 131.96(11) . . ?
C16 C17 C18 118.70(11) . . ?
C28 C27 C26 121.53(12) . . ?
C22 C23 C24 117.15(11) . . ?
C21 C22 C23 121.46(12) . . ?
C21 C20 C19 118.68(12) . . ?
C4 C3 C2 121.88(12) . . ?
C8 C9 C10 120.84(11) . . ?
C4 C5 C6 119.09(11) . . ?
C29 C28 C27 120.92(11) . . ?
C33 C32 C31 118.81(12) . . ?
C33 C34 C35 121.49(12) . . ?
C20 C21 C22 120.94(11) . . ?
C28 C29 C30 118.71(12) . . ?
C9 C10 C11 121.70(12) . . ?
C34 C33 C32 120.78(11) . . ?
C5 C4 C3 120.29(11) . . ?
C9 C8 C7 118.76(12) . . ?
C17 C16 C15 120.57(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.085
_oxdiff_exptl_absorpt_empirical_full_min 0.947

_chemical_name_common            TCPO
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_preparation       ', Luminescent'
