# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_0714se
_database_code_depnum_ccdc_archive 'CCDC 2116983'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Higashino'
;Kyoto University
Japan
;
_audit_update_record             
;
2021-10-21 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Dicarbonylpyrenopyrrole monoanion'
_chemical_melting_point          '295 oC'
_chemical_formula_moiety         'C24 H6 N5 O2, C24 H20 P'
_chemical_formula_sum            'C48 H26 N5 O2 P'
_chemical_formula_weight         735.71

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                   9.287(4)
_cell_length_b                   14.079(6)
_cell_length_c                   14.828(6)
_cell_angle_alpha                99.420(5)
_cell_angle_beta                 100.745(6)
_cell_angle_gamma                104.380(5)
_cell_volume                     1799.6(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4928
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            14684
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.013
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             7885
_reflns_number_gt                5395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7885
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2571(3) 0.0314(2) 0.74358(18) 0.0525(7) Uani 1 1 d . . . . .
H1 H 1.2284 0.0668 0.7943 0.063 Uiso 1 1 calc R U . . .
C2 C 1.3386(3) -0.0373(2) 0.75920(19) 0.0525(7) Uani 1 1 d . . . . .
H2 H 1.3657 -0.0484 0.8208 0.063 Uiso 1 1 calc R U . . .
C3 C 1.3802(3) -0.08917(18) 0.68655(18) 0.0427(6) Uani 1 1 d . . . . .
C4 C 1.4678(3) -0.16132(19) 0.7058(2) 0.0513(7) Uani 1 1 d . . . . .
C5 C 1.5111(3) -0.22019(18) 0.6250(2) 0.0508(7) Uani 1 1 d . . . . .
C6 C 1.4669(3) -0.20071(17) 0.53089(19) 0.0423(6) Uani 1 1 d . . . . .
C7 C 1.5095(3) -0.25123(17) 0.4573(2) 0.0504(7) Uani 1 1 d . . . . .
H3 H 1.5658 -0.2977 0.4686 0.060 Uiso 1 1 calc R U . . .
C8 C 1.4717(3) -0.23536(18) 0.3676(2) 0.0501(7) Uani 1 1 d . . . . .
H4 H 1.5017 -0.2707 0.3174 0.060 Uiso 1 1 calc R U . . .
C9 C 1.3897(3) -0.16745(16) 0.35112(18) 0.0399(6) Uani 1 1 d . . . . .
H5 H 1.3630 -0.1566 0.2894 0.048 Uiso 1 1 calc R U . . .
C10 C 1.3462(2) -0.11507(15) 0.42436(16) 0.0320(5) Uani 1 1 d . . . . .
C11 C 1.2668(2) -0.04116(15) 0.41027(15) 0.0287(5) Uani 1 1 d . . . . .
C12 C 1.2236(2) 0.01393(15) 0.48407(15) 0.0286(5) Uani 1 1 d . . . . .
C13 C 1.2590(2) -0.00317(16) 0.57862(15) 0.0326(5) Uani 1 1 d . . . . .
C14 C 1.2181(3) 0.04814(18) 0.65423(16) 0.0406(6) Uani 1 1 d . . . . .
H6 H 1.1625 0.0952 0.6440 0.049 Uiso 1 1 calc R U . . .
C15 C 1.3397(2) -0.07500(16) 0.59395(16) 0.0338(5) Uani 1 1 d . . . . .
C16 C 1.3838(2) -0.13047(15) 0.51678(17) 0.0342(5) Uani 1 1 d . . . . .
O1 O 1.5063(2) -0.17516(15) 0.78448(15) 0.0742(6) Uani 1 1 d . . . . .
O2 O 1.5819(2) -0.28113(13) 0.64030(16) 0.0670(6) Uani 1 1 d . . . . .
C17 C 1.1561(2) 0.07983(15) 0.44361(15) 0.0276(5) Uani 1 1 d . . . . .
C18 C 1.1636(2) 0.06053(15) 0.34770(15) 0.0267(5) Uani 1 1 d . . . . .
N1 N 1.23079(19) -0.01370(13) 0.32822(12) 0.0299(4) Uani 1 1 d . . . . .
C19 C 1.0995(3) 0.15579(17) 0.48901(16) 0.0345(5) Uani 1 1 d . . . . .
N2 N 1.0543(2) 0.21697(15) 0.52712(15) 0.0454(5) Uani 1 1 d . . . . .
C20 C 1.1200(2) 0.11003(15) 0.27546(16) 0.0298(5) Uani 1 1 d . . . . .
C21 C 1.0609(3) 0.19436(18) 0.29708(17) 0.0381(6) Uani 1 1 d . . . . .
N3 N 1.0153(3) 0.26290(18) 0.30991(17) 0.0587(7) Uani 1 1 d . . . . .
C22 C 1.1342(2) 0.08787(16) 0.18412(16) 0.0317(5) Uani 1 1 d . . . . .
C23 C 1.0999(3) 0.15017(19) 0.12081(17) 0.0396(6) Uani 1 1 d . . . . .
N4 N 1.0728(3) 0.20142(19) 0.07068(17) 0.0599(6) Uani 1 1 d . . . . .
C24 C 1.1901(3) 0.00854(18) 0.14526(17) 0.0400(6) Uani 1 1 d . . . . .
N5 N 1.2314(3) -0.05302(17) 0.10648(16) 0.0591(7) Uani 1 1 d . . . . .
P1 P 0.63113(6) 0.46951(4) 0.20923(4) 0.02659(15) Uani 1 1 d . . . . .
C25 C 0.6939(2) 0.45593(15) 0.32691(15) 0.0279(5) Uani 1 1 d . . . . .
C26 C 0.7812(2) 0.39078(16) 0.34595(15) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.8044 0.3506 0.2958 0.036 Uiso 1 1 calc R U . . .
C27 C 0.8338(2) 0.38478(17) 0.43786(16) 0.0361(5) Uani 1 1 d . . . . .
H8 H 0.8932 0.3404 0.4508 0.043 Uiso 1 1 calc R U . . .
C28 C 0.8001(2) 0.44331(18) 0.51103(16) 0.0386(6) Uani 1 1 d . . . . .
H9 H 0.8362 0.4389 0.5740 0.046 Uiso 1 1 calc R U . . .
C29 C 0.7139(3) 0.50833(18) 0.49268(16) 0.0399(6) Uani 1 1 d . . . . .
H10 H 0.6920 0.5490 0.5431 0.048 Uiso 1 1 calc R U . . .
C30 C 0.6596(3) 0.51414(17) 0.40112(16) 0.0358(5) Uani 1 1 d . . . . .
H11 H 0.5989 0.5578 0.3886 0.043 Uiso 1 1 calc R U . . .
C31 C 0.4520(2) 0.49953(15) 0.19939(14) 0.0285(5) Uani 1 1 d . . . . .
C32 C 0.3380(2) 0.44360(16) 0.23498(15) 0.0337(5) Uani 1 1 d . . . . .
H12 H 0.3560 0.3916 0.2651 0.040 Uiso 1 1 calc R U . . .
C33 C 0.1986(3) 0.46445(18) 0.22602(17) 0.0391(6) Uani 1 1 d . . . . .
H13 H 0.1206 0.4267 0.2501 0.047 Uiso 1 1 calc R U . . .
C34 C 0.1729(3) 0.53981(19) 0.18226(17) 0.0408(6) Uani 1 1 d . . . . .
H14 H 0.0771 0.5538 0.1767 0.049 Uiso 1 1 calc R U . . .
C35 C 0.2843(3) 0.59517(18) 0.14642(16) 0.0389(6) Uani 1 1 d . . . . .
H15 H 0.2651 0.6468 0.1161 0.047 Uiso 1 1 calc R U . . .
C36 C 0.4254(3) 0.57504(16) 0.15490(15) 0.0331(5) Uani 1 1 d . . . . .
H16 H 0.5028 0.6128 0.1304 0.040 Uiso 1 1 calc R U . . .
C37 C 0.7695(2) 0.57069(15) 0.18643(15) 0.0282(5) Uani 1 1 d . . . . .
C38 C 0.8607(2) 0.65064(16) 0.25938(17) 0.0370(6) Uani 1 1 d . . . . .
H17 H 0.8550 0.6501 0.3226 0.044 Uiso 1 1 calc R U . . .
C39 C 0.9603(3) 0.73147(17) 0.23867(19) 0.0435(6) Uani 1 1 d . . . . .
H18 H 1.0219 0.7866 0.2880 0.052 Uiso 1 1 calc R U . . .
C40 C 0.9697(3) 0.73184(18) 0.1476(2) 0.0462(7) Uani 1 1 d . . . . .
H19 H 1.0377 0.7875 0.1343 0.055 Uiso 1 1 calc R U . . .
C41 C 0.8815(3) 0.65238(18) 0.07478(18) 0.0417(6) Uani 1 1 d . . . . .
H20 H 0.8901 0.6529 0.0120 0.050 Uiso 1 1 calc R U . . .
C42 C 0.7806(2) 0.57191(17) 0.09380(16) 0.0343(5) Uani 1 1 d . . . . .
H21 H 0.7188 0.5175 0.0439 0.041 Uiso 1 1 calc R U . . .
C43 C 0.6049(2) 0.35839(15) 0.12187(14) 0.0280(5) Uani 1 1 d . . . . .
C44 C 0.4588(3) 0.30388(16) 0.06903(15) 0.0341(5) Uani 1 1 d . . . . .
H22 H 0.3726 0.3249 0.0795 0.041 Uiso 1 1 calc R U . . .
C45 C 0.4398(3) 0.21860(18) 0.00088(17) 0.0435(6) Uani 1 1 d . . . . .
H23 H 0.3401 0.1813 -0.0354 0.052 Uiso 1 1 calc R U . . .
C46 C 0.5638(3) 0.18766(18) -0.01462(17) 0.0448(6) Uani 1 1 d . . . . .
H24 H 0.5495 0.1290 -0.0613 0.054 Uiso 1 1 calc R U . . .
C47 C 0.7094(3) 0.24138(17) 0.03740(16) 0.0388(6) Uani 1 1 d . . . . .
H25 H 0.7947 0.2192 0.0269 0.047 Uiso 1 1 calc R U . . .
C48 C 0.7311(2) 0.32753(16) 0.10479(15) 0.0328(5) Uani 1 1 d . . . . .
H26 H 0.8315 0.3656 0.1393 0.039 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
C1 C14 1.381(3) . ?
C1 C2 1.391(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9500 . ?
C3 C15 1.414(3) . ?
C3 C4 1.481(4) . ?
C4 O1 1.217(3) . ?
C4 C5 1.518(4) . ?
C5 O2 1.228(3) . ?
C5 C6 1.469(4) . ?
C6 C7 1.378(4) . ?
C6 C16 1.415(3) . ?
C7 C8 1.381(4) . ?
C7 H3 0.9500 . ?
C8 C9 1.386(3) . ?
C8 H4 0.9500 . ?
C9 C10 1.392(3) . ?
C9 H5 0.9500 . ?
C10 C16 1.415(3) . ?
C10 C11 1.437(3) . ?
C11 N1 1.345(3) . ?
C11 C12 1.414(3) . ?
C12 C17 1.395(3) . ?
C12 C13 1.452(3) . ?
C13 C14 1.398(3) . ?
C13 C15 1.423(3) . ?
C14 H6 0.9500 . ?
C15 C16 1.459(3) . ?
C17 C18 1.421(3) . ?
C17 C19 1.431(3) . ?
C18 N1 1.363(3) . ?
C18 C20 1.421(3) . ?
C19 N2 1.160(3) . ?
C20 C22 1.377(3) . ?
C20 C21 1.442(3) . ?
C21 N3 1.148(3) . ?
C22 C24 1.428(3) . ?
C22 C23 1.431(3) . ?
C23 N4 1.154(3) . ?
C24 N5 1.146(3) . ?
P1 C37 1.791(2) . ?
P1 C25 1.791(2) . ?
P1 C43 1.793(2) . ?
P1 C31 1.802(2) . ?
C25 C26 1.395(3) . ?
C25 C30 1.396(3) . ?
C26 C27 1.383(3) . ?
C26 H7 0.9500 . ?
C27 C28 1.384(3) . ?
C27 H8 0.9500 . ?
C28 C29 1.385(3) . ?
C28 H9 0.9500 . ?
C29 C30 1.380(3) . ?
C29 H10 0.9500 . ?
C30 H11 0.9500 . ?
C31 C36 1.388(3) . ?
C31 C32 1.396(3) . ?
C32 C33 1.385(3) . ?
C32 H12 0.9500 . ?
C33 C34 1.378(3) . ?
C33 H13 0.9500 . ?
C34 C35 1.379(3) . ?
C34 H14 0.9500 . ?
C35 C36 1.396(3) . ?
C35 H15 0.9500 . ?
C36 H16 0.9500 . ?
C37 C38 1.393(3) . ?
C37 C42 1.399(3) . ?
C38 C39 1.394(3) . ?
C38 H17 0.9500 . ?
C39 C40 1.370(3) . ?
C39 H18 0.9500 . ?
C40 C41 1.381(3) . ?
C40 H19 0.9500 . ?
C41 C42 1.385(3) . ?
C41 H20 0.9500 . ?
C42 H21 0.9500 . ?
C43 C44 1.390(3) . ?
C43 C48 1.399(3) . ?
C44 C45 1.387(3) . ?
C44 H22 0.9500 . ?
C45 C46 1.373(3) . ?
C45 H23 0.9500 . ?
C46 C47 1.381(3) . ?
C46 H24 0.9500 . ?
C47 C48 1.384(3) . ?
C47 H25 0.9500 . ?
C48 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 119.9(3) . . ?
C14 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C15 120.9(3) . . ?
C2 C3 C4 119.2(2) . . ?
C15 C3 C4 119.9(2) . . ?
O1 C4 C3 122.1(3) . . ?
O1 C4 C5 118.7(3) . . ?
C3 C4 C5 119.2(2) . . ?
O2 C5 C6 122.6(3) . . ?
O2 C5 C4 119.4(3) . . ?
C6 C5 C4 117.9(2) . . ?
C7 C6 C16 121.0(2) . . ?
C7 C6 C5 118.6(2) . . ?
C16 C6 C5 120.4(2) . . ?
C6 C7 C8 121.1(2) . . ?
C6 C7 H3 119.5 . . ?
C8 C7 H3 119.5 . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H4 120.2 . . ?
C9 C8 H4 120.2 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H5 119.8 . . ?
C10 C9 H5 119.8 . . ?
C9 C10 C16 120.7(2) . . ?
C9 C10 C11 121.7(2) . . ?
C16 C10 C11 117.5(2) . . ?
N1 C11 C12 112.66(19) . . ?
N1 C11 C10 124.7(2) . . ?
C12 C11 C10 122.6(2) . . ?
C17 C12 C11 105.31(19) . . ?
C17 C12 C13 134.5(2) . . ?
C11 C12 C13 120.2(2) . . ?
C14 C13 C15 119.3(2) . . ?
C14 C13 C12 122.8(2) . . ?
C15 C13 C12 117.9(2) . . ?
C1 C14 C13 121.0(3) . . ?
C1 C14 H6 119.5 . . ?
C13 C14 H6 119.5 . . ?
C3 C15 C13 118.3(2) . . ?
C3 C15 C16 120.8(2) . . ?
C13 C15 C16 120.9(2) . . ?
C10 C16 C6 117.2(2) . . ?
C10 C16 C15 120.9(2) . . ?
C6 C16 C15 121.8(2) . . ?
C12 C17 C18 105.51(17) . . ?
C12 C17 C19 128.0(2) . . ?
C18 C17 C19 126.4(2) . . ?
N1 C18 C20 118.75(19) . . ?
N1 C18 C17 111.54(19) . . ?
C20 C18 C17 129.62(19) . . ?
C11 N1 C18 104.99(17) . . ?
N2 C19 C17 178.9(3) . . ?
C22 C20 C18 125.99(19) . . ?
C22 C20 C21 114.5(2) . . ?
C18 C20 C21 119.42(19) . . ?
N3 C21 C20 176.3(3) . . ?
C20 C22 C24 125.5(2) . . ?
C20 C22 C23 120.2(2) . . ?
C24 C22 C23 114.2(2) . . ?
N4 C23 C22 179.2(3) . . ?
N5 C24 C22 173.9(3) . . ?
C37 P1 C25 109.25(10) . . ?
C37 P1 C43 108.30(10) . . ?
C25 P1 C43 113.16(10) . . ?
C37 P1 C31 108.91(10) . . ?
C25 P1 C31 108.30(10) . . ?
C43 P1 C31 108.84(10) . . ?
C26 C25 C30 119.5(2) . . ?
C26 C25 P1 121.03(16) . . ?
C30 C25 P1 119.45(17) . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H7 120.0 . . ?
C25 C26 H7 120.0 . . ?
C26 C27 C28 120.1(2) . . ?
C26 C27 H8 119.9 . . ?
C28 C27 H8 119.9 . . ?
C29 C28 C27 120.2(2) . . ?
C29 C28 H9 119.9 . . ?
C27 C28 H9 119.9 . . ?
C30 C29 C28 120.0(2) . . ?
C30 C29 H10 120.0 . . ?
C28 C29 H10 120.0 . . ?
C29 C30 C25 120.2(2) . . ?
C29 C30 H11 119.9 . . ?
C25 C30 H11 119.9 . . ?
C36 C31 C32 120.24(19) . . ?
C36 C31 P1 120.82(16) . . ?
C32 C31 P1 118.91(17) . . ?
C33 C32 C31 119.5(2) . . ?
C33 C32 H12 120.3 . . ?
C31 C32 H12 120.3 . . ?
C34 C33 C32 120.1(2) . . ?
C34 C33 H13 119.9 . . ?
C32 C33 H13 119.9 . . ?
C33 C34 C35 120.9(2) . . ?
C33 C34 H14 119.6 . . ?
C35 C34 H14 119.6 . . ?
C34 C35 C36 119.7(2) . . ?
C34 C35 H15 120.2 . . ?
C36 C35 H15 120.2 . . ?
C31 C36 C35 119.6(2) . . ?
C31 C36 H16 120.2 . . ?
C35 C36 H16 120.2 . . ?
C38 C37 C42 119.7(2) . . ?
C38 C37 P1 120.63(17) . . ?
C42 C37 P1 119.57(16) . . ?
C37 C38 C39 119.3(2) . . ?
C37 C38 H17 120.3 . . ?
C39 C38 H17 120.3 . . ?
C40 C39 C38 120.4(2) . . ?
C40 C39 H18 119.8 . . ?
C38 C39 H18 119.8 . . ?
C39 C40 C41 120.9(2) . . ?
C39 C40 H19 119.6 . . ?
C41 C40 H19 119.6 . . ?
C40 C41 C42 119.6(2) . . ?
C40 C41 H20 120.2 . . ?
C42 C41 H20 120.2 . . ?
C41 C42 C37 120.1(2) . . ?
C41 C42 H21 120.0 . . ?
C37 C42 H21 120.0 . . ?
C44 C43 C48 119.64(19) . . ?
C44 C43 P1 120.02(16) . . ?
C48 C43 P1 120.32(16) . . ?
C45 C44 C43 119.6(2) . . ?
C45 C44 H22 120.2 . . ?
C43 C44 H22 120.2 . . ?
C46 C45 C44 120.6(2) . . ?
C46 C45 H23 119.7 . . ?
C44 C45 H23 119.7 . . ?
C45 C46 C47 120.3(2) . . ?
C45 C46 H24 119.9 . . ?
C47 C46 H24 119.9 . . ?
C46 C47 C48 120.1(2) . . ?
C46 C47 H25 119.9 . . ?
C48 C47 H25 119.9 . . ?
C47 C48 C43 119.8(2) . . ?
C47 C48 H26 120.1 . . ?
C43 C48 H26 120.1 . . ?

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
C14 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C15 -0.8(4) . . . . ?
C1 C2 C3 C4 179.6(2) . . . . ?
C2 C3 C4 O1 -1.1(4) . . . . ?
C15 C3 C4 O1 179.3(2) . . . . ?
C2 C3 C4 C5 178.8(2) . . . . ?
C15 C3 C4 C5 -0.8(3) . . . . ?
O1 C4 C5 O2 1.0(3) . . . . ?
C3 C4 C5 O2 -179.0(2) . . . . ?
O1 C4 C5 C6 -178.6(2) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
O2 C5 C6 C7 -1.5(3) . . . . ?
C4 C5 C6 C7 178.0(2) . . . . ?
O2 C5 C6 C16 179.3(2) . . . . ?
C4 C5 C6 C16 -1.2(3) . . . . ?
C16 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 -179.6(2) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C16 -0.4(3) . . . . ?
C8 C9 C10 C11 177.3(2) . . . . ?
C9 C10 C11 N1 -1.8(3) . . . . ?
C16 C10 C11 N1 176.02(18) . . . . ?
C9 C10 C11 C12 -179.01(19) . . . . ?
C16 C10 C11 C12 -1.2(3) . . . . ?
N1 C11 C12 C17 0.1(2) . . . . ?
C10 C11 C12 C17 177.61(18) . . . . ?
N1 C11 C12 C13 -177.66(17) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C17 C12 C13 C14 3.7(4) . . . . ?
C11 C12 C13 C14 -179.3(2) . . . . ?
C17 C12 C13 C15 -175.8(2) . . . . ?
C11 C12 C13 C15 1.1(3) . . . . ?
C2 C1 C14 C13 0.1(4) . . . . ?
C15 C13 C14 C1 1.1(3) . . . . ?
C12 C13 C14 C1 -178.4(2) . . . . ?
C2 C3 C15 C13 2.0(3) . . . . ?
C4 C3 C15 C13 -178.40(19) . . . . ?
C2 C3 C15 C16 -179.9(2) . . . . ?
C4 C3 C15 C16 -0.2(3) . . . . ?
C14 C13 C15 C3 -2.1(3) . . . . ?
C12 C13 C15 C3 177.44(18) . . . . ?
C14 C13 C15 C16 179.70(19) . . . . ?
C12 C13 C15 C16 -0.7(3) . . . . ?
C9 C10 C16 C6 0.1(3) . . . . ?
C11 C10 C16 C6 -177.76(18) . . . . ?
C9 C10 C16 C15 179.39(19) . . . . ?
C11 C10 C16 C15 1.6(3) . . . . ?
C7 C6 C16 C10 0.3(3) . . . . ?
C5 C6 C16 C10 179.54(19) . . . . ?
C7 C6 C16 C15 -179.0(2) . . . . ?
C5 C6 C16 C15 0.2(3) . . . . ?
C3 C15 C16 C10 -178.75(19) . . . . ?
C13 C15 C16 C10 -0.6(3) . . . . ?
C3 C15 C16 C6 0.6(3) . . . . ?
C13 C15 C16 C6 178.67(19) . . . . ?
C11 C12 C17 C18 -0.3(2) . . . . ?
C13 C12 C17 C18 177.0(2) . . . . ?
C11 C12 C17 C19 -176.7(2) . . . . ?
C13 C12 C17 C19 0.6(4) . . . . ?
C12 C17 C18 N1 0.4(2) . . . . ?
C19 C17 C18 N1 176.87(19) . . . . ?
C12 C17 C18 C20 -175.8(2) . . . . ?
C19 C17 C18 C20 0.7(4) . . . . ?
C12 C11 N1 C18 0.2(2) . . . . ?
C10 C11 N1 C18 -177.30(18) . . . . ?
C20 C18 N1 C11 176.30(18) . . . . ?
C17 C18 N1 C11 -0.4(2) . . . . ?
N1 C18 C20 C22 2.5(3) . . . . ?
C17 C18 C20 C22 178.5(2) . . . . ?
N1 C18 C20 C21 -174.74(19) . . . . ?
C17 C18 C20 C21 1.2(3) . . . . ?
C18 C20 C22 C24 2.4(4) . . . . ?
C21 C20 C22 C24 179.8(2) . . . . ?
C18 C20 C22 C23 -173.8(2) . . . . ?
C21 C20 C22 C23 3.6(3) . . . . ?
C37 P1 C25 C26 -91.77(19) . . . . ?
C43 P1 C25 C26 29.0(2) . . . . ?
C31 P1 C25 C26 149.73(17) . . . . ?
C37 P1 C25 C30 85.88(19) . . . . ?
C43 P1 C25 C30 -153.38(17) . . . . ?
C31 P1 C25 C30 -32.6(2) . . . . ?
C30 C25 C26 C27 -0.4(3) . . . . ?
P1 C25 C26 C27 177.24(16) . . . . ?
C25 C26 C27 C28 0.0(3) . . . . ?
C26 C27 C28 C29 -0.2(3) . . . . ?
C27 C28 C29 C30 0.8(4) . . . . ?
C28 C29 C30 C25 -1.2(4) . . . . ?
C26 C25 C30 C29 1.0(3) . . . . ?
P1 C25 C30 C29 -176.68(17) . . . . ?
C37 P1 C31 C36 16.4(2) . . . . ?
C25 P1 C31 C36 135.15(17) . . . . ?
C43 P1 C31 C36 -101.45(18) . . . . ?
C37 P1 C31 C32 -165.36(16) . . . . ?
C25 P1 C31 C32 -46.65(19) . . . . ?
C43 P1 C31 C32 76.76(19) . . . . ?
C36 C31 C32 C33 -0.4(3) . . . . ?
P1 C31 C32 C33 -178.58(17) . . . . ?
C31 C32 C33 C34 0.0(3) . . . . ?
C32 C33 C34 C35 0.3(4) . . . . ?
C33 C34 C35 C36 -0.3(4) . . . . ?
C32 C31 C36 C35 0.4(3) . . . . ?
P1 C31 C36 C35 178.56(17) . . . . ?
C34 C35 C36 C31 0.0(3) . . . . ?
C25 P1 C37 C38 -28.4(2) . . . . ?
C43 P1 C37 C38 -152.10(17) . . . . ?
C31 P1 C37 C38 89.68(19) . . . . ?
C25 P1 C37 C42 154.88(17) . . . . ?
C43 P1 C37 C42 31.2(2) . . . . ?
C31 P1 C37 C42 -87.00(18) . . . . ?
C42 C37 C38 C39 0.9(3) . . . . ?
P1 C37 C38 C39 -175.82(17) . . . . ?
C37 C38 C39 C40 -0.7(3) . . . . ?
C38 C39 C40 C41 -0.2(4) . . . . ?
C39 C40 C41 C42 1.0(4) . . . . ?
C40 C41 C42 C37 -0.8(3) . . . . ?
C38 C37 C42 C41 -0.1(3) . . . . ?
P1 C37 C42 C41 176.58(17) . . . . ?
C37 P1 C43 C44 -126.37(19) . . . . ?
C25 P1 C43 C44 112.35(19) . . . . ?
C31 P1 C43 C44 -8.1(2) . . . . ?
C37 P1 C43 C48 52.0(2) . . . . ?
C25 P1 C43 C48 -69.3(2) . . . . ?
C31 P1 C43 C48 170.23(17) . . . . ?
C48 C43 C44 C45 1.0(3) . . . . ?
P1 C43 C44 C45 179.30(18) . . . . ?
C43 C44 C45 C46 0.1(4) . . . . ?
C44 C45 C46 C47 -0.2(4) . . . . ?
C45 C46 C47 C48 -0.8(4) . . . . ?
C46 C47 C48 C43 1.8(4) . . . . ?
C44 C43 C48 C47 -1.9(3) . . . . ?
P1 C43 C48 C47 179.75(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C26 H7 N3 0.95 2.56 3.212(3) 126.4 .
C32 H12 O2 0.95 2.36 3.305(3) 171.7 2_756
C38 H17 N2 0.95 2.52 3.244(3) 133.5 2_766
C26 H7 N3 0.95 2.56 3.212(3) 126.4 .
C32 H12 O2 0.95 2.36 3.305(3) 171.7 2_756
C38 H17 N2 0.95 2.52 3.244(3) 133.5 2_766

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_0831se
_database_code_depnum_ccdc_archive 'CCDC 2116985'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Higashino'
;Kyoto University
Japan
;
_audit_update_record             
;
2021-10-21 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Pyrenopyrrole momoanion'
_chemical_melting_point          '110 oC'
_chemical_formula_moiety         'C24 H8 N5, C24 H20 P'
_chemical_formula_sum            'C48 H28 N5 P'
_chemical_formula_weight         705.72

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                   11.934(2)
_cell_length_b                   13.207(2)
_cell_length_c                   14.026(3)
_cell_angle_alpha                117.428(8)
_cell_angle_beta                 103.381(10)
_cell_angle_gamma                100.452(16)
_cell_volume                     1799.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    4896
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            14025
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             7549
_reflns_number_gt                3620
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7549
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1806(3) 0.3955(3) -0.0625(3) 0.0492(8) Uani 1 1 d . . . . .
H1 H 1.1545 0.3104 -0.1135 0.059 Uiso 1 1 calc R U . . .
C2 C 1.2615(3) 0.4713(3) -0.0775(3) 0.0608(10) Uani 1 1 d . . . . .
H2 H 1.2913 0.4373 -0.1384 0.073 Uiso 1 1 calc R U . . .
C3 C 1.2993(3) 0.5942(3) -0.0063(3) 0.0578(9) Uani 1 1 d . . . . .
H3 H 1.3535 0.6447 -0.0191 0.069 Uiso 1 1 calc R U . . .
C4 C 1.2586(3) 0.6462(3) 0.0854(3) 0.0481(8) Uani 1 1 d . . . . .
C5 C 1.2977(3) 0.7748(3) 0.1610(3) 0.0600(9) Uani 1 1 d . . . . .
H4 H 1.3513 0.8255 0.1480 0.072 Uiso 1 1 calc R U . . .
C6 C 1.2599(3) 0.8256(3) 0.2508(3) 0.0587(9) Uani 1 1 d . . . . .
H5 H 1.2879 0.9111 0.2999 0.070 Uiso 1 1 calc R U . . .
C7 C 1.1780(3) 0.7522(3) 0.2728(3) 0.0532(9) Uani 1 1 d . . . . .
C8 C 1.1373(3) 0.8035(3) 0.3653(3) 0.0673(10) Uani 1 1 d . . . . .
H6 H 1.1648 0.8890 0.4154 0.081 Uiso 1 1 calc R U . . .
C9 C 1.0576(3) 0.7310(3) 0.3840(3) 0.0630(10) Uani 1 1 d . . . . .
H7 H 1.0324 0.7672 0.4478 0.076 Uiso 1 1 calc R U . . .
C10 C 1.0144(3) 0.6075(3) 0.3118(3) 0.0514(8) Uani 1 1 d . . . . .
H8 H 0.9588 0.5591 0.3254 0.062 Uiso 1 1 calc R U . . .
C11 C 1.0517(2) 0.5525(3) 0.2183(2) 0.0416(7) Uani 1 1 d . . . . .
C12 C 1.0084(2) 0.4239(3) 0.1390(2) 0.0387(7) Uani 1 1 d . . . . .
C13 C 1.0510(2) 0.3696(3) 0.0469(2) 0.0362(7) Uani 1 1 d . . . . .
C14 C 1.1374(2) 0.4438(3) 0.0270(2) 0.0399(7) Uani 1 1 d . . . . .
C15 C 1.1774(2) 0.5706(3) 0.1033(3) 0.0409(7) Uani 1 1 d . . . . .
C16 C 1.1359(2) 0.6253(3) 0.1988(3) 0.0430(7) Uani 1 1 d . . . . .
N1 N 0.9270(2) 0.3426(2) 0.14285(19) 0.0400(6) Uani 1 1 d . . . . .
C17 C 0.9154(2) 0.2322(2) 0.0540(2) 0.0370(7) Uani 1 1 d . . . . .
C18 C 0.9922(2) 0.2453(3) -0.0076(2) 0.0389(7) Uani 1 1 d . . . . .
C19 C 1.0030(3) 0.1512(3) -0.1052(3) 0.0483(8) Uani 1 1 d . . . . .
N2 N 1.0113(3) 0.0757(2) -0.1852(3) 0.0705(10) Uani 1 1 d . . . . .
C20 C 0.8319(2) 0.1260(2) 0.0311(2) 0.0361(7) Uani 1 1 d . . . . .
C21 C 0.8337(3) 0.0116(3) -0.0523(3) 0.0454(8) Uani 1 1 d . . . . .
N3 N 0.8363(3) -0.0808(2) -0.1170(2) 0.0662(9) Uani 1 1 d . . . . .
C22 C 0.7465(3) 0.1220(2) 0.0831(2) 0.0401(7) Uani 1 1 d . . . . .
C23 C 0.7278(3) 0.2245(3) 0.1649(3) 0.0479(8) Uani 1 1 d . . . . .
N4 N 0.7038(3) 0.2995(3) 0.2309(3) 0.0775(10) Uani 1 1 d . . . . .
C24 C 0.6681(3) 0.0092(3) 0.0554(2) 0.0411(7) Uani 1 1 d . . . . .
N5 N 0.6019(3) -0.0788(2) 0.0357(2) 0.0564(8) Uani 1 1 d . . . . .
P1 P 0.61861(6) 0.69693(6) 0.44067(6) 0.0315(2) Uani 1 1 d . . . . .
C25 C 0.7449(2) 0.6727(2) 0.5137(2) 0.0338(6) Uani 1 1 d . . . . .
C26 C 0.7564(3) 0.5587(3) 0.4694(2) 0.0435(7) Uani 1 1 d . . . . .
H9 H 0.6933 0.4908 0.4027 0.052 Uiso 1 1 calc R U . . .
C27 C 0.8599(3) 0.5444(3) 0.5226(3) 0.0539(9) Uani 1 1 d . . . . .
H10 H 0.8678 0.4663 0.4918 0.065 Uiso 1 1 calc R U . . .
C28 C 0.9509(3) 0.6409(3) 0.6186(3) 0.0532(9) Uani 1 1 d . . . . .
H11 H 1.0215 0.6296 0.6543 0.064 Uiso 1 1 calc R U . . .
C29 C 0.9409(3) 0.7558(3) 0.6647(3) 0.0489(8) Uani 1 1 d . . . . .
H12 H 1.0047 0.8229 0.7313 0.059 Uiso 1 1 calc R U . . .
C30 C 0.8383(2) 0.7720(3) 0.6135(2) 0.0399(7) Uani 1 1 d . . . . .
H13 H 0.8305 0.8501 0.6455 0.048 Uiso 1 1 calc R U . . .
C31 C 0.6679(2) 0.7689(2) 0.3684(2) 0.0332(6) Uani 1 1 d . . . . .
C32 C 0.7901(3) 0.8382(3) 0.4075(3) 0.0521(8) Uani 1 1 d . . . . .
H14 H 0.8483 0.8495 0.4737 0.063 Uiso 1 1 calc R U . . .
C33 C 0.8254(3) 0.8905(3) 0.3481(3) 0.0603(10) Uani 1 1 d . . . . .
H15 H 0.9083 0.9382 0.3744 0.072 Uiso 1 1 calc R U . . .
C34 C 0.7432(3) 0.8747(3) 0.2530(3) 0.0481(8) Uani 1 1 d . . . . .
H16 H 0.7689 0.9112 0.2136 0.058 Uiso 1 1 calc R U . . .
C35 C 0.6224(3) 0.8055(3) 0.2136(3) 0.0449(8) Uani 1 1 d . . . . .
H17 H 0.5651 0.7942 0.1469 0.054 Uiso 1 1 calc R U . . .
C36 C 0.5849(3) 0.7531(2) 0.2709(2) 0.0391(7) Uani 1 1 d . . . . .
H18 H 0.5017 0.7058 0.2435 0.047 Uiso 1 1 calc R U . . .
C37 C 0.5584(2) 0.7889(2) 0.5425(2) 0.0321(6) Uani 1 1 d . . . . .
C38 C 0.4915(2) 0.8537(2) 0.5172(2) 0.0411(7) Uani 1 1 d . . . . .
H19 H 0.4832 0.8562 0.4493 0.049 Uiso 1 1 calc R U . . .
C39 C 0.4359(3) 0.9160(3) 0.5925(3) 0.0503(8) Uani 1 1 d . . . . .
H20 H 0.3892 0.9608 0.5758 0.060 Uiso 1 1 calc R U . . .
C40 C 0.4488(3) 0.9123(3) 0.6902(3) 0.0519(9) Uani 1 1 d . . . . .
H21 H 0.4115 0.9555 0.7414 0.062 Uiso 1 1 calc R U . . .
C41 C 0.5143(3) 0.8477(3) 0.7153(3) 0.0513(8) Uani 1 1 d . . . . .
H22 H 0.5219 0.8452 0.7831 0.062 Uiso 1 1 calc R U . . .
C42 C 0.5702(3) 0.7849(3) 0.6406(3) 0.0458(8) Uani 1 1 d . . . . .
H23 H 0.6161 0.7396 0.6574 0.055 Uiso 1 1 calc R U . . .
C43 C 0.4999(2) 0.5569(2) 0.3337(2) 0.0344(6) Uani 1 1 d . . . . .
C44 C 0.3888(2) 0.5238(3) 0.3462(3) 0.0416(7) Uani 1 1 d . . . . .
H24 H 0.3743 0.5765 0.4126 0.050 Uiso 1 1 calc R U . . .
C45 C 0.3003(3) 0.4145(3) 0.2617(3) 0.0503(8) Uani 1 1 d . . . . .
H25 H 0.2250 0.3913 0.2705 0.060 Uiso 1 1 calc R U . . .
C46 C 0.3204(3) 0.3387(3) 0.1647(3) 0.0534(9) Uani 1 1 d . . . . .
H26 H 0.2580 0.2641 0.1064 0.064 Uiso 1 1 calc R U . . .
C47 C 0.4294(3) 0.3692(3) 0.1510(3) 0.0539(9) Uani 1 1 d . . . . .
H27 H 0.4428 0.3157 0.0843 0.065 Uiso 1 1 calc R U . . .
C48 C 0.5192(3) 0.4785(3) 0.2353(2) 0.0470(8) Uani 1 1 d . . . . .
H28 H 0.5946 0.5004 0.2261 0.056 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
C1 C2 1.384(4) . ?
C1 C14 1.389(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.367(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(4) . ?
C3 H3 0.9500 . ?
C4 C15 1.412(4) . ?
C4 C5 1.431(4) . ?
C5 C6 1.354(4) . ?
C5 H4 0.9500 . ?
C6 C7 1.436(4) . ?
C6 H5 0.9500 . ?
C7 C8 1.407(4) . ?
C7 C16 1.411(4) . ?
C8 C9 1.381(5) . ?
C8 H6 0.9500 . ?
C9 C10 1.373(4) . ?
C9 H7 0.9500 . ?
C10 C11 1.398(4) . ?
C10 H8 0.9500 . ?
C11 C16 1.424(4) . ?
C11 C12 1.437(4) . ?
C12 N1 1.341(3) . ?
C12 C13 1.423(3) . ?
C13 C18 1.397(4) . ?
C13 C14 1.456(4) . ?
C14 C15 1.414(4) . ?
C15 C16 1.452(4) . ?
N1 C17 1.368(3) . ?
C17 C20 1.412(4) . ?
C17 C18 1.436(4) . ?
C18 C19 1.417(4) . ?
C19 N2 1.148(3) . ?
C20 C22 1.392(3) . ?
C20 C21 1.430(4) . ?
C21 N3 1.149(3) . ?
C22 C23 1.412(4) . ?
C22 C24 1.428(4) . ?
C23 N4 1.140(3) . ?
C24 N5 1.148(3) . ?
P1 C25 1.785(3) . ?
P1 C43 1.785(3) . ?
P1 C37 1.796(2) . ?
P1 C31 1.799(3) . ?
C25 C26 1.387(4) . ?
C25 C30 1.406(4) . ?
C26 C27 1.380(4) . ?
C26 H9 0.9500 . ?
C27 C28 1.363(4) . ?
C27 H10 0.9500 . ?
C28 C29 1.390(4) . ?
C28 H11 0.9500 . ?
C29 C30 1.374(4) . ?
C29 H12 0.9500 . ?
C30 H13 0.9500 . ?
C31 C36 1.390(4) . ?
C31 C32 1.396(4) . ?
C32 C33 1.392(4) . ?
C32 H14 0.9500 . ?
C33 C34 1.359(4) . ?
C33 H15 0.9500 . ?
C34 C35 1.381(4) . ?
C34 H16 0.9500 . ?
C35 C36 1.375(4) . ?
C35 H17 0.9500 . ?
C36 H18 0.9500 . ?
C37 C38 1.376(4) . ?
C37 C42 1.377(4) . ?
C38 C39 1.398(4) . ?
C38 H19 0.9500 . ?
C39 C40 1.369(4) . ?
C39 H20 0.9500 . ?
C40 C41 1.361(4) . ?
C40 H21 0.9500 . ?
C41 C42 1.398(4) . ?
C41 H22 0.9500 . ?
C42 H23 0.9500 . ?
C43 C44 1.396(4) . ?
C43 C48 1.396(4) . ?
C44 C45 1.377(4) . ?
C44 H24 0.9500 . ?
C45 C46 1.377(4) . ?
C45 H25 0.9500 . ?
C46 C47 1.374(4) . ?
C46 H26 0.9500 . ?
C47 C48 1.382(4) . ?
C47 H27 0.9500 . ?
C48 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C14 120.1(3) . . ?
C2 C1 H1 119.9 . . ?
C14 C1 H1 119.9 . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C15 119.4(3) . . ?
C3 C4 C5 121.1(3) . . ?
C15 C4 C5 119.5(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H4 119.3 . . ?
C4 C5 H4 119.3 . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H5 119.5 . . ?
C7 C6 H5 119.5 . . ?
C8 C7 C16 119.1(3) . . ?
C8 C7 C6 121.8(3) . . ?
C16 C7 C6 119.1(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H6 119.7 . . ?
C7 C8 H6 119.7 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H7 119.5 . . ?
C8 C9 H7 119.5 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H8 119.8 . . ?
C11 C10 H8 119.8 . . ?
C10 C11 C16 119.6(3) . . ?
C10 C11 C12 122.9(3) . . ?
C16 C11 C12 117.5(3) . . ?
N1 C12 C13 112.8(2) . . ?
N1 C12 C11 125.3(2) . . ?
C13 C12 C11 121.9(3) . . ?
C18 C13 C12 105.1(2) . . ?
C18 C13 C14 134.1(2) . . ?
C12 C13 C14 120.8(3) . . ?
C1 C14 C15 119.7(3) . . ?
C1 C14 C13 123.1(3) . . ?
C15 C14 C13 117.3(2) . . ?
C4 C15 C14 119.2(3) . . ?
C4 C15 C16 119.0(3) . . ?
C14 C15 C16 121.7(3) . . ?
C7 C16 C11 119.2(3) . . ?
C7 C16 C15 119.9(3) . . ?
C11 C16 C15 120.8(3) . . ?
C12 N1 C17 105.5(2) . . ?
N1 C17 C20 120.0(2) . . ?
N1 C17 C18 110.9(2) . . ?
C20 C17 C18 129.0(2) . . ?
C13 C18 C19 127.5(2) . . ?
C13 C18 C17 105.7(2) . . ?
C19 C18 C17 126.8(3) . . ?
N2 C19 C18 178.9(4) . . ?
C22 C20 C17 125.6(2) . . ?
C22 C20 C21 116.1(2) . . ?
C17 C20 C21 118.3(2) . . ?
N3 C21 C20 178.2(4) . . ?
C20 C22 C23 124.8(2) . . ?
C20 C22 C24 121.0(2) . . ?
C23 C22 C24 114.2(2) . . ?
N4 C23 C22 173.3(3) . . ?
N5 C24 C22 176.9(3) . . ?
C25 P1 C43 111.11(13) . . ?
C25 P1 C37 109.56(13) . . ?
C43 P1 C37 108.66(12) . . ?
C25 P1 C31 109.33(12) . . ?
C43 P1 C31 107.44(13) . . ?
C37 P1 C31 110.72(12) . . ?
C26 C25 C30 119.4(3) . . ?
C26 C25 P1 121.0(2) . . ?
C30 C25 P1 119.5(2) . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H9 120.2 . . ?
C25 C26 H9 120.2 . . ?
C28 C27 C26 120.8(3) . . ?
C28 C27 H10 119.6 . . ?
C26 C27 H10 119.6 . . ?
C27 C28 C29 120.3(3) . . ?
C27 C28 H11 119.8 . . ?
C29 C28 H11 119.8 . . ?
C30 C29 C28 119.8(3) . . ?
C30 C29 H12 120.1 . . ?
C28 C29 H12 120.1 . . ?
C29 C30 C25 119.9(3) . . ?
C29 C30 H13 120.0 . . ?
C25 C30 H13 120.0 . . ?
C36 C31 C32 119.2(3) . . ?
C36 C31 P1 120.1(2) . . ?
C32 C31 P1 120.6(2) . . ?
C33 C32 C31 119.0(3) . . ?
C33 C32 H14 120.5 . . ?
C31 C32 H14 120.5 . . ?
C34 C33 C32 121.1(3) . . ?
C34 C33 H15 119.4 . . ?
C32 C33 H15 119.4 . . ?
C33 C34 C35 120.0(3) . . ?
C33 C34 H16 120.0 . . ?
C35 C34 H16 120.0 . . ?
C36 C35 C34 120.1(3) . . ?
C36 C35 H17 120.0 . . ?
C34 C35 H17 120.0 . . ?
C35 C36 C31 120.5(3) . . ?
C35 C36 H18 119.8 . . ?
C31 C36 H18 119.8 . . ?
C38 C37 C42 120.5(2) . . ?
C38 C37 P1 120.0(2) . . ?
C42 C37 P1 119.3(2) . . ?
C37 C38 C39 119.2(3) . . ?
C37 C38 H19 120.4 . . ?
C39 C38 H19 120.4 . . ?
C40 C39 C38 120.0(3) . . ?
C40 C39 H20 120.0 . . ?
C38 C39 H20 120.0 . . ?
C41 C40 C39 121.0(3) . . ?
C41 C40 H21 119.5 . . ?
C39 C40 H21 119.5 . . ?
C40 C41 C42 119.6(3) . . ?
C40 C41 H22 120.2 . . ?
C42 C41 H22 120.2 . . ?
C37 C42 C41 119.7(3) . . ?
C37 C42 H23 120.1 . . ?
C41 C42 H23 120.1 . . ?
C44 C43 C48 119.3(3) . . ?
C44 C43 P1 121.7(2) . . ?
C48 C43 P1 119.0(2) . . ?
C45 C44 C43 119.7(3) . . ?
C45 C44 H24 120.2 . . ?
C43 C44 H24 120.2 . . ?
C44 C45 C46 120.3(3) . . ?
C44 C45 H25 119.8 . . ?
C46 C45 H25 119.8 . . ?
C47 C46 C45 121.0(3) . . ?
C47 C46 H26 119.5 . . ?
C45 C46 H26 119.5 . . ?
C46 C47 C48 119.3(3) . . ?
C46 C47 H27 120.3 . . ?
C48 C47 H27 120.3 . . ?
C47 C48 C43 120.4(3) . . ?
C47 C48 H28 119.8 . . ?
C43 C48 H28 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 -0.8(5) . . . . ?
C1 C2 C3 C4 1.4(5) . . . . ?
C2 C3 C4 C15 -0.4(5) . . . . ?
C2 C3 C4 C5 179.7(3) . . . . ?
C3 C4 C5 C6 -179.2(3) . . . . ?
C15 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C5 C6 C7 C16 -0.5(5) . . . . ?
C16 C7 C8 C9 0.3(5) . . . . ?
C6 C7 C8 C9 179.4(3) . . . . ?
C7 C8 C9 C10 -1.3(5) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C9 C10 C11 C16 0.6(5) . . . . ?
C9 C10 C11 C12 -179.2(3) . . . . ?
C10 C11 C12 N1 1.5(5) . . . . ?
C16 C11 C12 N1 -178.3(3) . . . . ?
C10 C11 C12 C13 -177.7(3) . . . . ?
C16 C11 C12 C13 2.5(4) . . . . ?
N1 C12 C13 C18 -1.3(3) . . . . ?
C11 C12 C13 C18 178.0(3) . . . . ?
N1 C12 C13 C14 178.3(3) . . . . ?
C11 C12 C13 C14 -2.4(4) . . . . ?
C2 C1 C14 C15 -0.6(5) . . . . ?
C2 C1 C14 C13 179.2(3) . . . . ?
C18 C13 C14 C1 0.3(5) . . . . ?
C12 C13 C14 C1 -179.1(3) . . . . ?
C18 C13 C14 C15 -179.9(3) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C3 C4 C15 C14 -1.0(4) . . . . ?
C5 C4 C15 C14 178.9(3) . . . . ?
C3 C4 C15 C16 179.8(3) . . . . ?
C5 C4 C15 C16 -0.3(4) . . . . ?
C1 C14 C15 C4 1.5(4) . . . . ?
C13 C14 C15 C4 -178.3(3) . . . . ?
C1 C14 C15 C16 -179.3(3) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C8 C7 C16 C11 1.1(4) . . . . ?
C6 C7 C16 C11 -178.0(3) . . . . ?
C8 C7 C16 C15 -179.7(3) . . . . ?
C6 C7 C16 C15 1.2(4) . . . . ?
C10 C11 C16 C7 -1.6(4) . . . . ?
C12 C11 C16 C7 178.3(3) . . . . ?
C10 C11 C16 C15 179.2(3) . . . . ?
C12 C11 C16 C15 -1.0(4) . . . . ?
C4 C15 C16 C7 -0.7(4) . . . . ?
C14 C15 C16 C7 -179.9(3) . . . . ?
C4 C15 C16 C11 178.5(3) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C13 C12 N1 C17 0.9(3) . . . . ?
C11 C12 N1 C17 -178.4(3) . . . . ?
C12 N1 C17 C20 -177.6(3) . . . . ?
C12 N1 C17 C18 -0.2(3) . . . . ?
C12 C13 C18 C19 179.6(3) . . . . ?
C14 C13 C18 C19 0.1(5) . . . . ?
C12 C13 C18 C17 1.1(3) . . . . ?
C14 C13 C18 C17 -178.4(3) . . . . ?
N1 C17 C18 C13 -0.6(3) . . . . ?
C20 C17 C18 C13 176.5(3) . . . . ?
N1 C17 C18 C19 -179.1(3) . . . . ?
C20 C17 C18 C19 -2.0(5) . . . . ?
N1 C17 C20 C22 7.9(4) . . . . ?
C18 C17 C20 C22 -169.0(3) . . . . ?
N1 C17 C20 C21 -171.9(3) . . . . ?
C18 C17 C20 C21 11.2(5) . . . . ?
C17 C20 C22 C23 2.1(5) . . . . ?
C21 C20 C22 C23 -178.1(3) . . . . ?
C17 C20 C22 C24 -178.5(3) . . . . ?
C21 C20 C22 C24 1.3(4) . . . . ?
C43 P1 C25 C26 14.9(3) . . . . ?
C37 P1 C25 C26 135.0(2) . . . . ?
C31 P1 C25 C26 -103.5(2) . . . . ?
C43 P1 C25 C30 -169.3(2) . . . . ?
C37 P1 C25 C30 -49.2(2) . . . . ?
C31 P1 C25 C30 72.3(2) . . . . ?
C30 C25 C26 C27 -1.0(4) . . . . ?
P1 C25 C26 C27 174.8(2) . . . . ?
C25 C26 C27 C28 0.4(5) . . . . ?
C26 C27 C28 C29 -0.1(5) . . . . ?
C27 C28 C29 C30 0.4(4) . . . . ?
C28 C29 C30 C25 -1.1(4) . . . . ?
C26 C25 C30 C29 1.4(4) . . . . ?
P1 C25 C30 C29 -174.5(2) . . . . ?
C25 P1 C31 C36 153.2(2) . . . . ?
C43 P1 C31 C36 32.5(2) . . . . ?
C37 P1 C31 C36 -86.0(2) . . . . ?
C25 P1 C31 C32 -25.1(3) . . . . ?
C43 P1 C31 C32 -145.7(2) . . . . ?
C37 P1 C31 C32 95.7(2) . . . . ?
C36 C31 C32 C33 0.5(4) . . . . ?
P1 C31 C32 C33 178.7(2) . . . . ?
C31 C32 C33 C34 -0.3(5) . . . . ?
C32 C33 C34 C35 -0.1(5) . . . . ?
C33 C34 C35 C36 0.3(4) . . . . ?
C34 C35 C36 C31 -0.1(4) . . . . ?
C32 C31 C36 C35 -0.3(4) . . . . ?
P1 C31 C36 C35 -178.5(2) . . . . ?
C25 P1 C37 C38 157.6(2) . . . . ?
C43 P1 C37 C38 -80.8(2) . . . . ?
C31 P1 C37 C38 37.0(3) . . . . ?
C25 P1 C37 C42 -28.4(3) . . . . ?
C43 P1 C37 C42 93.1(2) . . . . ?
C31 P1 C37 C42 -149.1(2) . . . . ?
C42 C37 C38 C39 0.3(4) . . . . ?
P1 C37 C38 C39 174.2(2) . . . . ?
C37 C38 C39 C40 0.2(4) . . . . ?
C38 C39 C40 C41 -0.7(5) . . . . ?
C39 C40 C41 C42 0.6(5) . . . . ?
C38 C37 C42 C41 -0.4(4) . . . . ?
P1 C37 C42 C41 -174.3(2) . . . . ?
C40 C41 C42 C37 0.0(5) . . . . ?
C25 P1 C43 C44 110.1(2) . . . . ?
C37 P1 C43 C44 -10.5(3) . . . . ?
C31 P1 C43 C44 -130.3(2) . . . . ?
C25 P1 C43 C48 -69.6(3) . . . . ?
C37 P1 C43 C48 169.8(2) . . . . ?
C31 P1 C43 C48 49.9(3) . . . . ?
C48 C43 C44 C45 0.2(4) . . . . ?
P1 C43 C44 C45 -179.5(2) . . . . ?
C43 C44 C45 C46 -0.8(5) . . . . ?
C44 C45 C46 C47 1.2(5) . . . . ?
C45 C46 C47 C48 -1.0(5) . . . . ?
C46 C47 C48 C43 0.4(5) . . . . ?
C44 C43 C48 C47 0.0(5) . . . . ?
P1 C43 C48 C47 179.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C26 H9 N4 0.95 2.62 3.317(4) 130.8 .
C26 H9 N4 0.95 2.62 3.317(4) 130.8 .
C26 H9 N4 0.95 2.62 3.317(4) 130.8 .
C26 H9 N4 0.95 2.62 3.317(4) 130.8 .

_refine_diff_density_max         1.764
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.058

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_0807se
_database_code_depnum_ccdc_archive 'CCDC 2116984'
loop_
_audit_author_name
_audit_author_address
'Tomohiro Higashino'
;Kyoto University
Japan
;
_audit_update_record             
;
2021-10-21 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Pyrenodipyrrole dianion'
_chemical_melting_point          '246 oC'
_chemical_formula_moiety         '0.5(C32 H6 N10), C24 H20 P, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C40.50 H24 Cl N5 P'
_chemical_formula_weight         647.07

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.529(2)
_cell_length_b                   30.222(9)
_cell_length_c                   13.985(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.770(4)
_cell_angle_gamma                90
_cell_volume                     3178.4(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7590
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.210
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            21495
_diffrn_reflns_av_unetI/netI     0.1320
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.026
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             7059
_reflns_number_gt                3143
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1118P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7059
_refine_ls_number_parameters     442
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.2670
_refine_ls_wR_factor_gt          0.2445
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0289(5) 0.06130(12) 0.0296(3) 0.0369(9) Uani 1 1 d . . . . .
C2 C -0.0489(5) 0.02096(11) -0.0060(2) 0.0344(9) Uani 1 1 d . . . . .
C3 C -0.2225(5) 0.02229(12) -0.0490(2) 0.0357(9) Uani 1 1 d . . . . .
C4 C -0.3156(6) 0.06260(13) -0.0559(3) 0.0401(9) Uani 1 1 d . . . . .
H1 H -0.4326 0.0633 -0.0844 0.048 Uiso 1 1 calc R U . . .
C5 C -0.2365(6) 0.10150(13) -0.0209(3) 0.0436(10) Uani 1 1 d . . . . .
H2 H -0.3000 0.1286 -0.0256 0.052 Uiso 1 1 calc R U . . .
C6 C -0.0678(6) 0.10069(13) 0.0201(3) 0.0411(9) Uani 1 1 d . . . . .
H3 H -0.0151 0.1275 0.0426 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2084(5) 0.05955(12) 0.0741(3) 0.0386(9) Uani 1 1 d . . . . .
C8 C 0.3009(5) 0.01873(12) 0.0860(3) 0.0352(9) Uani 1 1 d . . . . .
C9 C 0.4584(6) 0.02903(14) 0.1338(3) 0.0413(10) Uani 1 1 d . . . . .
C10 C 0.4531(6) 0.07611(14) 0.1494(3) 0.0448(10) Uani 1 1 d . . . . .
N1 N 0.2995(5) 0.09439(11) 0.1110(2) 0.0428(8) Uani 1 1 d . . . . .
C11 C 0.6027(7) 0.00090(16) 0.1620(3) 0.0548(12) Uani 1 1 d . . . . .
N2 N 0.7216(6) -0.02298(15) 0.1846(3) 0.0674(12) Uani 1 1 d . . . . .
C12 C 0.5849(6) 0.10459(15) 0.1997(3) 0.0506(11) Uani 1 1 d . . . . .
C13 C 0.5786(6) 0.14999(15) 0.2067(3) 0.0500(11) Uani 1 1 d . . . . .
C14 C 0.7267(8) 0.08392(17) 0.2506(4) 0.0616(13) Uani 1 1 d . . . . .
N3 N 0.8542(7) 0.07025(14) 0.2951(3) 0.0854(15) Uani 1 1 d . . . . .
C15 C 0.6909(6) 0.17321(16) 0.2699(3) 0.0546(12) Uani 1 1 d . . . . .
N4 N 0.7785(6) 0.19391(16) 0.3259(3) 0.0792(14) Uani 1 1 d . . . . .
C16 C 0.4570(7) 0.17872(17) 0.1507(3) 0.0559(12) Uani 1 1 d . . . . .
N5 N 0.3789(6) 0.20592(15) 0.1098(3) 0.0737(13) Uani 1 1 d . . . . .
P1 P 0.60326(16) 0.34417(4) 0.11818(8) 0.0430(3) Uani 1 1 d . . . . .
C17 C 0.4802(6) 0.33951(13) 0.2241(3) 0.0414(10) Uani 1 1 d . . . . .
C18 C 0.4993(6) 0.30383(15) 0.2864(3) 0.0535(12) Uani 1 1 d . . . . .
H4 H 0.5814 0.2809 0.2738 0.064 Uiso 1 1 calc R U . . .
C19 C 0.4003(7) 0.30152(18) 0.3661(4) 0.0668(14) Uani 1 1 d . . . . .
H5 H 0.4145 0.2772 0.4087 0.080 Uiso 1 1 calc R U . . .
C20 C 0.2797(7) 0.33464(18) 0.3844(3) 0.0629(14) Uani 1 1 d . . . . .
H6 H 0.2111 0.3328 0.4396 0.076 Uiso 1 1 calc R U . . .
C21 C 0.2581(7) 0.37034(16) 0.3231(3) 0.0598(13) Uani 1 1 d . . . . .
H7 H 0.1748 0.3929 0.3359 0.072 Uiso 1 1 calc R U . . .
C22 C 0.3576(6) 0.37287(15) 0.2439(3) 0.0511(11) Uani 1 1 d . . . . .
H8 H 0.3435 0.3975 0.2019 0.061 Uiso 1 1 calc R U . . .
C23 C 0.7476(6) 0.29722(14) 0.1081(3) 0.0477(11) Uani 1 1 d . . . . .
C24 C 0.7184(7) 0.26574(16) 0.0383(4) 0.0648(14) Uani 1 1 d . . . . .
H9 H 0.6221 0.2687 -0.0077 0.078 Uiso 1 1 calc R U . . .
C25 C 0.8331(7) 0.22916(18) 0.0359(5) 0.0789(17) Uani 1 1 d . . . . .
H10 H 0.8150 0.2071 -0.0121 0.095 Uiso 1 1 calc R U . . .
C26 C 0.9695(7) 0.22535(18) 0.1020(5) 0.0816(18) Uani 1 1 d . . . . .
H11 H 1.0439 0.2000 0.1013 0.098 Uiso 1 1 calc R U . . .
C27 C 1.0022(7) 0.25702(17) 0.1694(4) 0.0668(14) Uani 1 1 d . . . . .
H12 H 1.1022 0.2544 0.2131 0.080 Uiso 1 1 calc R U . . .
C28 C 0.8903(6) 0.29304(16) 0.1746(4) 0.0581(12) Uani 1 1 d . . . . .
H13 H 0.9105 0.3148 0.2230 0.070 Uiso 1 1 calc R U . . .
C29 C 0.7477(6) 0.39128(13) 0.1224(3) 0.0434(10) Uani 1 1 d . . . . .
C30 C 0.7590(7) 0.41959(16) 0.2006(3) 0.0621(14) Uani 1 1 d . . . . .
H14 H 0.6832 0.4156 0.2523 0.075 Uiso 1 1 calc R U . . .
C31 C 0.8859(7) 0.45472(18) 0.2025(4) 0.0741(16) Uani 1 1 d . . . . .
H15 H 0.8974 0.4739 0.2563 0.089 Uiso 1 1 calc R U . . .
C32 C 0.9912(7) 0.46066(18) 0.1260(4) 0.0682(15) Uani 1 1 d . . . . .
H16 H 1.0746 0.4843 0.1269 0.082 Uiso 1 1 calc R U . . .
C33 C 0.9776(6) 0.43324(16) 0.0492(3) 0.0596(13) Uani 1 1 d . . . . .
H17 H 1.0497 0.4382 -0.0036 0.072 Uiso 1 1 calc R U . . .
C34 C 0.8593(6) 0.39792(15) 0.0471(3) 0.0518(11) Uani 1 1 d . . . . .
H18 H 0.8545 0.3782 -0.0060 0.062 Uiso 1 1 calc R U . . .
C35 C 0.4438(6) 0.34714(14) 0.0196(3) 0.0467(11) Uani 1 1 d . . . . .
C36 C 0.4382(6) 0.38272(16) -0.0453(3) 0.0538(12) Uani 1 1 d . . . . .
H19 H 0.5239 0.4057 -0.0384 0.065 Uiso 1 1 calc R U . . .
C37 C 0.3079(7) 0.38459(18) -0.1198(3) 0.0635(13) Uani 1 1 d . . . . .
H20 H 0.3042 0.4086 -0.1636 0.076 Uiso 1 1 calc R U . . .
C38 C 0.1836(7) 0.3506(2) -0.1286(4) 0.0679(15) Uani 1 1 d . . . . .
H21 H 0.0958 0.3512 -0.1797 0.082 Uiso 1 1 calc R U . . .
C39 C 0.1860(6) 0.31655(17) -0.0649(4) 0.0599(13) Uani 1 1 d . . . . .
H22 H 0.1001 0.2936 -0.0717 0.072 Uiso 1 1 calc R U . . .
C40 C 0.3128(6) 0.31529(16) 0.0094(3) 0.0583(12) Uani 1 1 d . . . . .
H23 H 0.3101 0.2919 0.0547 0.070 Uiso 1 1 calc R U . . .
C41 C 0.3928(16) 0.4997(5) -0.0113(9) 0.090(4) Uani 0.5 1 d D . P A -1
H24 H 0.3108 0.5253 -0.0166 0.107 Uiso 0.5 1 calc R U P A -1
H25 H 0.3201 0.4728 -0.0220 0.107 Uiso 0.5 1 calc R U P A -1
Cl1 Cl 0.5318(4) 0.50339(9) -0.10102(19) 0.0621(7) Uani 0.5 1 d D . P A -1
Cl2 Cl 0.474(3) 0.4982(5) 0.0963(11) 0.450(12) Uani 0.5 1 d D . P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.398(5) . ?
C1 C2 1.431(5) . ?
C1 C7 1.462(5) . ?
C2 C3 1.412(5) . ?
C2 C2 1.471(7) 3 ?
C3 C4 1.406(5) . ?
C3 C8 1.457(5) 3 ?
C4 C5 1.396(5) . ?
C4 H1 0.9500 . ?
C5 C6 1.368(6) . ?
C5 H2 0.9500 . ?
C6 H3 0.9500 . ?
C7 N1 1.346(5) . ?
C7 C8 1.422(5) . ?
C8 C9 1.369(5) . ?
C8 C3 1.457(5) 3 ?
C9 C11 1.420(6) . ?
C9 C10 1.440(6) . ?
C10 N1 1.368(5) . ?
C10 C12 1.467(6) . ?
C11 N2 1.181(6) . ?
C12 C13 1.376(6) . ?
C12 C14 1.401(7) . ?
C13 C15 1.385(6) . ?
C13 C16 1.462(7) . ?
C14 N3 1.193(6) . ?
C15 N4 1.179(6) . ?
C16 N5 1.147(6) . ?
P1 C35 1.786(5) . ?
P1 C17 1.791(4) . ?
P1 C29 1.791(4) . ?
P1 C23 1.797(4) . ?
C17 C18 1.389(5) . ?
C17 C22 1.404(6) . ?
C18 C19 1.373(6) . ?
C18 H4 0.9500 . ?
C19 C20 1.384(7) . ?
C19 H5 0.9500 . ?
C20 C21 1.383(6) . ?
C20 H6 0.9500 . ?
C21 C22 1.369(6) . ?
C21 H7 0.9500 . ?
C22 H8 0.9500 . ?
C23 C24 1.374(6) . ?
C23 C28 1.392(6) . ?
C24 C25 1.404(7) . ?
C24 H9 0.9500 . ?
C25 C26 1.353(8) . ?
C25 H10 0.9500 . ?
C26 C27 1.358(7) . ?
C26 H11 0.9500 . ?
C27 C28 1.380(6) . ?
C27 H12 0.9500 . ?
C28 H13 0.9500 . ?
C29 C30 1.388(6) . ?
C29 C34 1.393(5) . ?
C30 C31 1.428(6) . ?
C30 H14 0.9500 . ?
C31 C32 1.374(6) . ?
C31 H15 0.9500 . ?
C32 C33 1.356(6) . ?
C32 H16 0.9500 . ?
C33 C34 1.390(6) . ?
C33 H17 0.9500 . ?
C34 H18 0.9500 . ?
C35 C40 1.381(6) . ?
C35 C36 1.406(6) . ?
C36 C37 1.398(6) . ?
C36 H19 0.9500 . ?
C37 C38 1.390(7) . ?
C37 H20 0.9500 . ?
C38 C39 1.362(7) . ?
C38 H21 0.9500 . ?
C39 C40 1.377(6) . ?
C39 H22 0.9500 . ?
C40 H23 0.9500 . ?
C41 Cl2 1.596(16) . ?
C41 Cl1 1.676(12) . ?
C41 H24 0.9900 . ?
C41 H25 0.9900 . ?

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
C6 C1 C2 119.3(4) . . ?
C6 C1 C7 122.5(3) . . ?
C2 C1 C7 118.2(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 C2 121.4(4) . 3 ?
C1 C2 C2 120.0(4) . 3 ?
C4 C3 C2 120.1(4) . . ?
C4 C3 C8 121.4(4) . 3 ?
C2 C3 C8 118.5(3) . 3 ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H1 119.9 . . ?
C3 C4 H1 119.9 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H2 119.9 . . ?
C4 C5 H2 119.9 . . ?
C5 C6 C1 121.6(4) . . ?
C5 C6 H3 119.2 . . ?
C1 C6 H3 119.2 . . ?
N1 C7 C8 113.3(4) . . ?
N1 C7 C1 125.4(4) . . ?
C8 C7 C1 121.2(3) . . ?
C9 C8 C7 105.5(3) . . ?
C9 C8 C3 133.9(4) . 3 ?
C7 C8 C3 120.6(4) . 3 ?
C8 C9 C11 129.2(4) . . ?
C8 C9 C10 105.6(4) . . ?
C11 C9 C10 125.2(4) . . ?
N1 C10 C9 111.7(4) . . ?
N1 C10 C12 119.4(4) . . ?
C9 C10 C12 129.0(4) . . ?
C7 N1 C10 103.9(3) . . ?
N2 C11 C9 179.0(5) . . ?
C13 C12 C14 115.9(4) . . ?
C13 C12 C10 126.4(4) . . ?
C14 C12 C10 117.6(4) . . ?
C12 C13 C15 121.9(4) . . ?
C12 C13 C16 125.2(4) . . ?
C15 C13 C16 112.9(4) . . ?
N3 C14 C12 173.7(5) . . ?
N4 C15 C13 176.4(5) . . ?
N5 C16 C13 170.2(5) . . ?
C35 P1 C17 106.72(19) . . ?
C35 P1 C29 111.7(2) . . ?
C17 P1 C29 111.89(18) . . ?
C35 P1 C23 111.5(2) . . ?
C17 P1 C23 109.97(19) . . ?
C29 P1 C23 105.2(2) . . ?
C18 C17 C22 118.9(4) . . ?
C18 C17 P1 122.5(3) . . ?
C22 C17 P1 118.6(3) . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H4 119.8 . . ?
C17 C18 H4 119.8 . . ?
C18 C19 C20 120.0(4) . . ?
C18 C19 H5 120.0 . . ?
C20 C19 H5 120.0 . . ?
C21 C20 C19 120.6(4) . . ?
C21 C20 H6 119.7 . . ?
C19 C20 H6 119.7 . . ?
C22 C21 C20 119.5(4) . . ?
C22 C21 H7 120.3 . . ?
C20 C21 H7 120.3 . . ?
C21 C22 C17 120.7(4) . . ?
C21 C22 H8 119.7 . . ?
C17 C22 H8 119.7 . . ?
C24 C23 C28 120.2(4) . . ?
C24 C23 P1 121.7(4) . . ?
C28 C23 P1 118.0(3) . . ?
C23 C24 C25 119.0(5) . . ?
C23 C24 H9 120.5 . . ?
C25 C24 H9 120.5 . . ?
C26 C25 C24 119.8(5) . . ?
C26 C25 H10 120.1 . . ?
C24 C25 H10 120.1 . . ?
C25 C26 C27 121.4(5) . . ?
C25 C26 H11 119.3 . . ?
C27 C26 H11 119.3 . . ?
C26 C27 C28 120.1(5) . . ?
C26 C27 H12 119.9 . . ?
C28 C27 H12 119.9 . . ?
C27 C28 C23 119.3(5) . . ?
C27 C28 H13 120.3 . . ?
C23 C28 H13 120.3 . . ?
C30 C29 C34 119.4(4) . . ?
C30 C29 P1 122.0(3) . . ?
C34 C29 P1 118.5(3) . . ?
C29 C30 C31 119.2(4) . . ?
C29 C30 H14 120.4 . . ?
C31 C30 H14 120.4 . . ?
C32 C31 C30 119.6(4) . . ?
C32 C31 H15 120.2 . . ?
C30 C31 H15 120.2 . . ?
C33 C32 C31 120.8(5) . . ?
C33 C32 H16 119.6 . . ?
C31 C32 H16 119.6 . . ?
C32 C33 C34 120.7(4) . . ?
C32 C33 H17 119.6 . . ?
C34 C33 H17 119.6 . . ?
C33 C34 C29 120.2(4) . . ?
C33 C34 H18 119.9 . . ?
C29 C34 H18 119.9 . . ?
C40 C35 C36 117.9(4) . . ?
C40 C35 P1 119.7(4) . . ?
C36 C35 P1 122.3(3) . . ?
C37 C36 C35 120.7(4) . . ?
C37 C36 H19 119.7 . . ?
C35 C36 H19 119.7 . . ?
C38 C37 C36 118.8(5) . . ?
C38 C37 H20 120.6 . . ?
C36 C37 H20 120.6 . . ?
C39 C38 C37 120.9(5) . . ?
C39 C38 H21 119.6 . . ?
C37 C38 H21 119.6 . . ?
C38 C39 C40 120.1(5) . . ?
C38 C39 H22 120.0 . . ?
C40 C39 H22 120.0 . . ?
C39 C40 C35 121.6(5) . . ?
C39 C40 H23 119.2 . . ?
C35 C40 H23 119.2 . . ?
Cl2 C41 Cl1 118.9(12) . . ?
Cl2 C41 H24 107.6 . . ?
Cl1 C41 H24 107.6 . . ?
Cl2 C41 H25 107.6 . . ?
Cl1 C41 H25 107.6 . . ?
H24 C41 H25 107.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(5) . . . . ?
C7 C1 C2 C3 179.8(3) . . . . ?
C6 C1 C2 C2 -178.2(4) . . . 3 ?
C7 C1 C2 C2 2.2(6) . . . 3 ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C2 C3 C4 177.4(4) 3 . . . ?
C1 C2 C3 C8 179.4(3) . . . 3 ?
C2 C2 C3 C8 -3.1(6) 3 . . 3 ?
C2 C3 C4 C5 0.4(5) . . . . ?
C8 C3 C4 C5 -179.1(3) 3 . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C2 C1 C6 C5 1.2(6) . . . . ?
C7 C1 C6 C5 -179.2(4) . . . . ?
C6 C1 C7 N1 0.5(6) . . . . ?
C2 C1 C7 N1 -179.9(3) . . . . ?
C6 C1 C7 C8 177.6(3) . . . . ?
C2 C1 C7 C8 -2.8(5) . . . . ?
N1 C7 C8 C9 0.4(4) . . . . ?
C1 C7 C8 C9 -177.0(3) . . . . ?
N1 C7 C8 C3 -179.1(3) . . . 3 ?
C1 C7 C8 C3 3.5(5) . . . 3 ?
C7 C8 C9 C11 -178.3(4) . . . . ?
C3 C8 C9 C11 1.1(7) 3 . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C3 C8 C9 C10 179.8(4) 3 . . . ?
C8 C9 C10 N1 -1.1(4) . . . . ?
C11 C9 C10 N1 177.6(4) . . . . ?
C8 C9 C10 C12 178.1(4) . . . . ?
C11 C9 C10 C12 -3.2(6) . . . . ?
C8 C7 N1 C10 -1.1(4) . . . . ?
C1 C7 N1 C10 176.2(3) . . . . ?
C9 C10 N1 C7 1.4(4) . . . . ?
C12 C10 N1 C7 -177.9(3) . . . . ?
N1 C10 C12 C13 -5.7(6) . . . . ?
C9 C10 C12 C13 175.1(4) . . . . ?
N1 C10 C12 C14 170.3(4) . . . . ?
C9 C10 C12 C14 -8.8(6) . . . . ?
C14 C12 C13 C15 -8.3(6) . . . . ?
C10 C12 C13 C15 167.8(4) . . . . ?
C14 C12 C13 C16 171.9(4) . . . . ?
C10 C12 C13 C16 -12.0(7) . . . . ?
C35 P1 C17 C18 120.8(4) . . . . ?
C29 P1 C17 C18 -116.7(4) . . . . ?
C23 P1 C17 C18 -0.2(4) . . . . ?
C35 P1 C17 C22 -58.0(4) . . . . ?
C29 P1 C17 C22 64.4(4) . . . . ?
C23 P1 C17 C22 -179.1(3) . . . . ?
C22 C17 C18 C19 -0.3(7) . . . . ?
P1 C17 C18 C19 -179.2(4) . . . . ?
C17 C18 C19 C20 0.5(7) . . . . ?
C18 C19 C20 C21 -0.2(8) . . . . ?
C19 C20 C21 C22 -0.2(8) . . . . ?
C20 C21 C22 C17 0.4(7) . . . . ?
C18 C17 C22 C21 -0.1(7) . . . . ?
P1 C17 C22 C21 178.8(3) . . . . ?
C35 P1 C23 C24 -7.4(5) . . . . ?
C17 P1 C23 C24 110.8(4) . . . . ?
C29 P1 C23 C24 -128.6(4) . . . . ?
C35 P1 C23 C28 173.5(3) . . . . ?
C17 P1 C23 C28 -68.3(4) . . . . ?
C29 P1 C23 C28 52.3(4) . . . . ?
C28 C23 C24 C25 0.9(7) . . . . ?
P1 C23 C24 C25 -178.2(4) . . . . ?
C23 C24 C25 C26 0.2(8) . . . . ?
C24 C25 C26 C27 -2.2(9) . . . . ?
C25 C26 C27 C28 3.2(9) . . . . ?
C26 C27 C28 C23 -2.1(7) . . . . ?
C24 C23 C28 C27 0.1(7) . . . . ?
P1 C23 C28 C27 179.2(3) . . . . ?
C35 P1 C29 C30 120.0(4) . . . . ?
C17 P1 C29 C30 0.5(5) . . . . ?
C23 P1 C29 C30 -118.9(4) . . . . ?
C35 P1 C29 C34 -63.8(4) . . . . ?
C17 P1 C29 C34 176.6(3) . . . . ?
C23 P1 C29 C34 57.2(4) . . . . ?
C34 C29 C30 C31 -0.5(7) . . . . ?
P1 C29 C30 C31 175.6(4) . . . . ?
C29 C30 C31 C32 1.7(8) . . . . ?
C30 C31 C32 C33 -0.8(9) . . . . ?
C31 C32 C33 C34 -1.4(8) . . . . ?
C32 C33 C34 C29 2.6(7) . . . . ?
C30 C29 C34 C33 -1.6(7) . . . . ?
P1 C29 C34 C33 -177.8(4) . . . . ?
C17 P1 C35 C40 -52.5(4) . . . . ?
C29 P1 C35 C40 -175.0(3) . . . . ?
C23 P1 C35 C40 67.6(4) . . . . ?
C17 P1 C35 C36 122.9(4) . . . . ?
C29 P1 C35 C36 0.3(4) . . . . ?
C23 P1 C35 C36 -117.0(4) . . . . ?
C40 C35 C36 C37 -2.5(6) . . . . ?
P1 C35 C36 C37 -177.9(3) . . . . ?
C35 C36 C37 C38 0.1(7) . . . . ?
C36 C37 C38 C39 1.3(7) . . . . ?
C37 C38 C39 C40 -0.1(7) . . . . ?
C38 C39 C40 C35 -2.4(7) . . . . ?
C36 C35 C40 C39 3.7(6) . . . . ?
P1 C35 C40 C39 179.3(4) . . . . ?

_refine_diff_density_max         0.681
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.072

_shelxl_version_number           2014-3



