#------------------------------------------------------------------------------
#$Date: 2025-10-06 11:48:12 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302688 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/56/1575624.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1575624
loop_
_publ_author_name
'Artem'ev, Alexander V.'
'Davydova, Maria P.'
'Kuzmin, Anton V.'
'Rakhmanova, Mariana I.'
'Bagryanskaya, Irina Yu'
_publ_section_title
;
 A tetraphosphino-bis(s-triazine) from cyanuric chloride and
 Ph₂PH: new unexpected tandem C-C/C-P coupling reaction.
;
_journal_issue                   38
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14440
_journal_page_last               14447
_journal_paper_doi               10.1039/d5dt01861g
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C54 H40 N6 P4, C H4 O'
_chemical_formula_sum            'C55 H44 N6 O P4'
_chemical_formula_weight         928.84
_chemical_name_systematic
;
 4,4',6,6'-Tetrakis(diphenylphosphino)-2,2'-bis(1,3,5-triazine)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-08-20 deposited with the CCDC.	2025-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                112.326(8)
_cell_angle_beta                 98.243(8)
_cell_angle_gamma                91.295(8)
_cell_formula_units_Z            2
_cell_length_a                   11.630(3)
_cell_length_b                   15.246(4)
_cell_length_c                   15.743(5)
_cell_measurement_reflns_used    1767
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      20.08
_cell_measurement_theta_min      2.64
_cell_volume                     2546.4(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_unetI/netI     0.1317
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21751
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        22.463
_diffrn_reflns_theta_max         22.463
_diffrn_reflns_theta_min         2.195
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     609
_refine_ls_number_reflns         6621
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0752P)²+2.1111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3680
_reflns_number_total             6621
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01861g2.cif
_cod_data_source_block           md660
_cod_depositor_comments
'Adding full bibliography for 1575624--1575626.cif.'
_cod_original_cell_volume        2546.5(12)
_cod_database_code               1575624
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.846
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.28695(14) 0.96560(11) 0.61069(12) 0.0345(5) Uani 1 1 d . . . . .
P2 P 0.78718(14) 0.64872(12) 0.27405(12) 0.0374(5) Uani 1 1 d . . . . .
P3 P 0.76568(13) 0.61748(11) 0.59837(11) 0.0327(4) Uani 1 1 d . . . . .
P4 P 0.10933(13) 0.67999(11) 0.29436(12) 0.0342(5) Uani 1 1 d . . . . .
N5 N 0.4232(4) 0.8261(3) 0.5143(3) 0.0275(12) Uani 1 1 d . . . . .
N6 N 0.7482(4) 0.6301(3) 0.4311(3) 0.0308(12) Uani 1 1 d . . . . .
N1 N 0.5935(4) 0.6926(3) 0.3613(3) 0.0289(12) Uani 1 1 d . . . . .
N2 N 0.2261(4) 0.8213(3) 0.4460(3) 0.0315(12) Uani 1 1 d . . . . .
N3 N 0.3449(4) 0.7015(3) 0.3682(3) 0.0298(12) Uani 1 1 d . . . . .
N4 N 0.5868(4) 0.6834(3) 0.5082(3) 0.0292(12) Uani 1 1 d . . . . .
C1 C 0.6455(6) 1.0953(6) 0.7900(5) 0.066(2) Uani 1 1 d . . . . .
H1 H 0.718188 1.122091 0.828891 0.079 Uiso 1 1 calc R U . . .
C2 C 0.5855(6) 1.1427(5) 0.7419(5) 0.056(2) Uani 1 1 d . . . . .
H9 H 0.617224 1.202910 0.747419 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4800(5) 1.1047(4) 0.6855(4) 0.0388(16) Uani 1 1 d . . . . .
H6 H 0.440268 1.139464 0.653179 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4310(5) 1.0176(4) 0.6750(4) 0.0338(15) Uani 1 1 d . . . . .
C5 C 0.3188(5) 0.8617(4) 0.5129(4) 0.0253(14) Uani 1 1 d . . . . .
C6 C 0.4299(5) 0.7477(4) 0.4400(4) 0.0269(14) Uani 1 1 d . . . . .
C7 C 0.5449(5) 0.7057(4) 0.4368(4) 0.0260(14) Uani 1 1 d . . . . .
C8 C 0.6975(5) 0.6555(4) 0.3627(4) 0.0289(14) Uani 1 1 d . . . . .
C9 C 0.7931(5) 0.5194(5) 0.2155(5) 0.0385(16) Uani 1 1 d . . . . .
C10 C 0.8121(5) 0.4597(5) 0.2638(5) 0.0437(17) Uani 1 1 d . . . . .
H28 H 0.815050 0.484321 0.329388 0.052 Uiso 1 1 calc R U . . .
C11 C 0.8266(6) 0.3652(5) 0.2165(6) 0.055(2) Uani 1 1 d . . . . .
H27 H 0.838756 0.325004 0.250042 0.065 Uiso 1 1 calc R U . . .
C12 C 0.8239(6) 0.3276(5) 0.1218(6) 0.062(2) Uani 1 1 d . . . . .
H2 H 0.834556 0.262218 0.090312 0.075 Uiso 1 1 calc R U . . .
C13 C 0.1459(6) 1.1455(4) 0.4474(5) 0.0512(19) Uani 1 1 d . . . . .
H3 H 0.114337 1.181440 0.413106 0.061 Uiso 1 1 calc R U . . .
C14 C 0.2501(6) 1.1060(4) 0.4317(5) 0.0469(18) Uani 1 1 d . . . . .
H4 H 0.290393 1.115604 0.387195 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2970(5) 1.0520(4) 0.4805(4) 0.0375(16) Uani 1 1 d . . . . .
H5 H 0.368386 1.024299 0.468734 0.045 Uiso 1 1 calc R U . . .
C16 C 0.2382(5) 1.0390(4) 0.5471(4) 0.0305(15) Uani 1 1 d . . . . .
C17 C 0.5985(7) 1.0087(6) 0.7811(5) 0.069(2) Uani 1 1 d . . . . .
H7 H 0.638928 0.974967 0.814279 0.083 Uiso 1 1 calc R U . . .
C18 C 0.4930(6) 0.9697(5) 0.7244(5) 0.056(2) Uani 1 1 d . . . . .
H8 H 0.462039 0.909228 0.718821 0.067 Uiso 1 1 calc R U . . .
C19 C 0.2425(5) 0.7408(4) 0.3753(4) 0.0295(15) Uani 1 1 d . . . . .
C20 C 0.6889(5) 0.6456(4) 0.5022(4) 0.0284(14) Uani 1 1 d . . . . .
C21 C 0.6505(5) 0.6183(4) 0.6659(4) 0.0319(15) Uani 1 1 d . . . . .
C22 C 0.6072(5) 0.5392(4) 0.6777(4) 0.0399(17) Uani 1 1 d . . . . .
H10 H 0.633598 0.478832 0.645435 0.048 Uiso 1 1 calc R U . . .
C23 C 0.5265(6) 0.5465(5) 0.7354(5) 0.0492(19) Uani 1 1 d . . . . .
H11 H 0.497254 0.490977 0.741718 0.059 Uiso 1 1 calc R U . . .
C24 C 0.4879(6) 0.6321(6) 0.7837(5) 0.058(2) Uani 1 1 d . . . . .
H12 H 0.432760 0.636750 0.823984 0.070 Uiso 1 1 calc R U . . .
C25 C 0.5299(7) 0.7116(6) 0.7732(5) 0.068(2) Uani 1 1 d . . . . .
H14 H 0.502714 0.771555 0.805959 0.081 Uiso 1 1 calc R U . . .
C26 C 0.6121(6) 0.7056(5) 0.7150(5) 0.055(2) Uani 1 1 d . . . . .
H13 H 0.641626 0.761309 0.709286 0.066 Uiso 1 1 calc R U . . .
C27 C 0.7875(5) 0.4929(4) 0.5358(4) 0.0324(15) Uani 1 1 d . . . . .
C28 C 0.6996(6) 0.4276(4) 0.4708(4) 0.0411(17) Uani 1 1 d . . . . .
H15 H 0.623836 0.446953 0.459605 0.049 Uiso 1 1 calc R U . . .
C29 C 0.7237(6) 0.3340(5) 0.4227(5) 0.0477(18) Uani 1 1 d . . . . .
H19 H 0.664290 0.289178 0.378998 0.057 Uiso 1 1 calc R U . . .
C30 C 0.8345(7) 0.3070(5) 0.4393(5) 0.052(2) Uani 1 1 d . . . . .
H16 H 0.850965 0.243190 0.406938 0.063 Uiso 1 1 calc R U . . .
C31 C 0.9212(6) 0.3713(5) 0.5018(5) 0.0516(19) Uani 1 1 d . . . . .
H17 H 0.997537 0.352429 0.511812 0.062 Uiso 1 1 calc R U . . .
C32 C 0.8965(5) 0.4637(4) 0.5500(4) 0.0378(16) Uani 1 1 d . . . . .
H18 H 0.956369 0.507789 0.593903 0.045 Uiso 1 1 calc R U . . .
C33 C 0.6898(5) 0.6805(4) 0.1901(4) 0.0371(16) Uani 1 1 d . . . . .
C34 C 0.7251(6) 0.7616(4) 0.1779(5) 0.0478(18) Uani 1 1 d . . . . .
H20 H 0.796189 0.797466 0.212447 0.057 Uiso 1 1 calc R U . . .
C35 C 0.6571(8) 0.7906(5) 0.1154(6) 0.065(2) Uani 1 1 d . . . . .
H24 H 0.681696 0.846700 0.107994 0.078 Uiso 1 1 calc R U . . .
C36 C 0.5554(7) 0.7402(6) 0.0642(5) 0.060(2) Uani 1 1 d . . . . .
H21 H 0.510151 0.760438 0.020930 0.073 Uiso 1 1 calc R U . . .
C37 C 0.5196(6) 0.6613(6) 0.0756(5) 0.058(2) Uani 1 1 d . . . . .
H22 H 0.447860 0.626971 0.040726 0.069 Uiso 1 1 calc R U . . .
C38 C 0.5853(6) 0.6289(5) 0.1371(5) 0.0463(18) Uani 1 1 d . . . . .
H23 H 0.559556 0.572293 0.143111 0.056 Uiso 1 1 calc R U . . .
C39 C 0.8058(6) 0.3849(6) 0.0734(5) 0.061(2) Uani 1 1 d . . . . .
H25 H 0.801852 0.359189 0.007756 0.073 Uiso 1 1 calc R U . . .
C40 C 0.7933(6) 0.4808(5) 0.1202(5) 0.057(2) Uani 1 1 d . . . . .
H26 H 0.784629 0.520845 0.086352 0.068 Uiso 1 1 calc R U . . .
C41 C 0.0794(5) 0.7594(4) 0.2323(4) 0.0339(15) Uani 1 1 d . . . . .
C42 C 0.0814(5) 0.8575(5) 0.2795(5) 0.0447(17) Uani 1 1 d . . . . .
H29 H 0.106661 0.885005 0.344941 0.054 Uiso 1 1 calc R U . . .
C43 C 0.0472(6) 0.9154(5) 0.2327(5) 0.0491(18) Uani 1 1 d . . . . .
H30 H 0.049392 0.982194 0.266268 0.059 Uiso 1 1 calc R U . . .
C44 C 0.0104(6) 0.8779(5) 0.1388(5) 0.055(2) Uani 1 1 d . . . . .
H31 H -0.013232 0.918376 0.107314 0.067 Uiso 1 1 calc R U . . .
C45 C 0.0077(6) 0.7816(5) 0.0900(5) 0.056(2) Uani 1 1 d . . . . .
H32 H -0.016375 0.755414 0.024446 0.067 Uiso 1 1 calc R U . . .
C46 C 0.0401(6) 0.7218(5) 0.1365(5) 0.0483(18) Uani 1 1 d . . . . .
H33 H 0.035336 0.654928 0.102558 0.058 Uiso 1 1 calc R U . . .
C47 C 0.1618(5) 0.5762(4) 0.2116(4) 0.0338(15) Uani 1 1 d . . . . .
C48 C 0.2501(5) 0.5764(5) 0.1598(4) 0.0426(17) Uani 1 1 d . . . . .
H34 H 0.287378 0.635127 0.166123 0.051 Uiso 1 1 calc R U . . .
C49 C 0.2833(6) 0.4919(5) 0.0995(4) 0.0461(18) Uani 1 1 d . . . . .
H35 H 0.343864 0.492969 0.065259 0.055 Uiso 1 1 calc R U . . .
C50 C 0.2298(6) 0.4067(5) 0.0888(5) 0.055(2) Uani 1 1 d . . . . .
H36 H 0.252577 0.349177 0.046312 0.066 Uiso 1 1 calc R U . . .
C51 C 0.1435(6) 0.4037(5) 0.1388(5) 0.056(2) Uani 1 1 d . . . . .
H37 H 0.107125 0.344321 0.131566 0.068 Uiso 1 1 calc R U . . .
C52 C 0.1094(5) 0.4882(4) 0.2003(5) 0.0424(17) Uani 1 1 d . . . . .
H38 H 0.049757 0.485927 0.234964 0.051 Uiso 1 1 calc R U . . .
C53 C 0.1335(5) 1.0795(4) 0.5619(5) 0.0423(17) Uani 1 1 d . . . . .
H40 H 0.092667 1.070508 0.606498 0.051 Uiso 1 1 calc R U . . .
C54 C 0.0873(6) 1.1330(4) 0.5126(5) 0.0506(19) Uani 1 1 d . . . . .
H39 H 0.015814 1.160732 0.523915 0.061 Uiso 1 1 calc R U . . .
O1M O 0.021743 0.125592 0.108911 0.196(8) Uani 0.5 1 d D U P . .
H1M H 0.086727 0.117258 0.090951 0.294 Uiso 0.5 1 d . U P . .
C1M C 0.045(2) 0.1665(13) 0.2081(7) 0.141(9) Uani 0.5 1 d D U P . .
H1MA H 0.114850 0.142139 0.230402 0.211 Uiso 0.5 1 calc R U P . .
H1MB H -0.021847 0.149585 0.232408 0.211 Uiso 0.5 1 calc R U P . .
H1MC H 0.056325 0.235871 0.229588 0.211 Uiso 0.5 1 calc R U P . .
O2M O 0.174053 0.016418 0.018471 0.344(16) Uani 0.5 1 d D U P . .
H2M H 0.185585 -0.002010 0.062708 0.516 Uiso 0.5 1 d . U P . .
C2M C 0.207(3) -0.0545(17) -0.0674(14) 0.259(18) Uani 0.5 1 d D U P . .
H2MA H 0.163951 -0.046047 -0.121839 0.388 Uiso 0.5 1 calc R U P . .
H2MB H 0.186632 -0.118753 -0.071124 0.388 Uiso 0.5 1 calc R U P . .
H2MC H 0.290585 -0.045480 -0.066151 0.388 Uiso 0.5 1 calc R U P . .
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'
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
C16 P1 C4 106.1(3) . . ?
C16 P1 C5 98.5(3) . . ?
C4 P1 C5 103.1(3) . . ?
C8 P2 C33 103.4(3) . . ?
C8 P2 C9 101.6(3) . . ?
C33 P2 C9 104.1(3) . . ?
C21 P3 C27 106.2(3) . . ?
C21 P3 C20 102.3(3) . . ?
C27 P3 C20 100.2(3) . . ?
C47 P4 C19 102.8(3) . . ?
C47 P4 C41 104.9(3) . . ?
C19 P4 C41 101.3(3) . . ?
C6 N5 C5 113.9(5) . . ?
C20 N6 C8 115.5(5) . . ?
C7 N1 C8 114.1(5) . . ?
C5 N2 C19 116.3(5) . . ?
C6 N3 C19 114.0(5) . . ?
C7 N4 C20 114.6(5) . . ?
C2 C1 C17 118.6(7) . . ?
C2 C1 H1 120.7 . . ?
C17 C1 H1 120.7 . . ?
C1 C2 C3 121.3(7) . . ?
C1 C2 H9 119.4 . . ?
C3 C2 H9 119.4 . . ?
C4 C3 C2 121.4(6) . . ?
C4 C3 H6 119.3 . . ?
C2 C3 H6 119.3 . . ?
C3 C4 C18 116.9(6) . . ?
C3 C4 P1 125.0(5) . . ?
C18 C4 P1 117.9(5) . . ?
N5 C5 N2 124.5(5) . . ?
N5 C5 P1 121.6(4) . . ?
N2 C5 P1 113.7(4) . . ?
N5 C6 N3 127.4(5) . . ?
N5 C6 C7 116.4(5) . . ?
N3 C6 C7 116.2(5) . . ?
N4 C7 N1 126.8(5) . . ?
N4 C7 C6 116.5(5) . . ?
N1 C7 C6 116.7(5) . . ?
N6 C8 N1 124.3(5) . . ?
N6 C8 P2 115.1(4) . . ?
N1 C8 P2 120.3(4) . . ?
C40 C9 C10 117.8(6) . . ?
C40 C9 P2 118.9(5) . . ?
C10 C9 P2 122.8(5) . . ?
C11 C10 C9 120.0(7) . . ?
C11 C10 H28 120.0 . . ?
C9 C10 H28 120.0 . . ?
C10 C11 C12 121.5(7) . . ?
C10 C11 H27 119.3 . . ?
C12 C11 H27 119.3 . . ?
C39 C12 C11 119.4(7) . . ?
C39 C12 H2 120.3 . . ?
C11 C12 H2 120.3 . . ?
C54 C13 C14 120.1(6) . . ?
C54 C13 H3 119.9 . . ?
C14 C13 H3 119.9 . . ?
C13 C14 C15 120.8(7) . . ?
C13 C14 H4 119.6 . . ?
C15 C14 H4 119.6 . . ?
C14 C15 C16 119.6(6) . . ?
C14 C15 H5 120.2 . . ?
C16 C15 H5 120.2 . . ?
C53 C16 C15 118.8(6) . . ?
C53 C16 P1 117.6(5) . . ?
C15 C16 P1 123.5(5) . . ?
C1 C17 C18 120.7(7) . . ?
C1 C17 H7 119.7 . . ?
C18 C17 H7 119.7 . . ?
C17 C18 C4 121.2(7) . . ?
C17 C18 H8 119.4 . . ?
C4 C18 H8 119.4 . . ?
N3 C19 N2 123.9(5) . . ?
N3 C19 P4 121.3(4) . . ?
N2 C19 P4 114.5(4) . . ?
N4 C20 N6 124.7(5) . . ?
N4 C20 P3 120.9(5) . . ?
N6 C20 P3 114.3(4) . . ?
C22 C21 C26 118.2(6) . . ?
C22 C21 P3 124.3(5) . . ?
C26 C21 P3 117.2(5) . . ?
C21 C22 C23 121.1(6) . . ?
C21 C22 H10 119.4 . . ?
C23 C22 H10 119.4 . . ?
C24 C23 C22 121.0(7) . . ?
C24 C23 H11 119.5 . . ?
C22 C23 H11 119.5 . . ?
C23 C24 C25 118.9(7) . . ?
C23 C24 H12 120.5 . . ?
C25 C24 H12 120.5 . . ?
C24 C25 C26 120.9(7) . . ?
C24 C25 H14 119.6 . . ?
C26 C25 H14 119.6 . . ?
C21 C26 C25 119.9(7) . . ?
C21 C26 H13 120.1 . . ?
C25 C26 H13 120.1 . . ?
C32 C27 C28 119.1(6) . . ?
C32 C27 P3 118.0(5) . . ?
C28 C27 P3 122.9(5) . . ?
C29 C28 C27 119.8(6) . . ?
C29 C28 H15 120.1 . . ?
C27 C28 H15 120.1 . . ?
C30 C29 C28 119.4(6) . . ?
C30 C29 H19 120.3 . . ?
C28 C29 H19 120.3 . . ?
C31 C30 C29 120.8(6) . . ?
C31 C30 H16 119.6 . . ?
C29 C30 H16 119.6 . . ?
C30 C31 C32 119.5(6) . . ?
C30 C31 H17 120.2 . . ?
C32 C31 H17 120.2 . . ?
C27 C32 C31 121.3(6) . . ?
C27 C32 H18 119.3 . . ?
C31 C32 H18 119.3 . . ?
C34 C33 C38 118.4(6) . . ?
C34 C33 P2 116.2(5) . . ?
C38 C33 P2 125.4(5) . . ?
C33 C34 C35 120.1(7) . . ?
C33 C34 H20 120.0 . . ?
C35 C34 H20 120.0 . . ?
C36 C35 C34 121.3(7) . . ?
C36 C35 H24 119.4 . . ?
C34 C35 H24 119.4 . . ?
C37 C36 C35 119.4(7) . . ?
C37 C36 H21 120.3 . . ?
C35 C36 H21 120.3 . . ?
C36 C37 C38 121.5(7) . . ?
C36 C37 H22 119.2 . . ?
C38 C37 H22 119.2 . . ?
C37 C38 C33 119.4(6) . . ?
C37 C38 H23 120.3 . . ?
C33 C38 H23 120.3 . . ?
C12 C39 C40 119.9(7) . . ?
C12 C39 H25 120.0 . . ?
C40 C39 H25 120.0 . . ?
C39 C40 C9 121.4(7) . . ?
C39 C40 H26 119.3 . . ?
C9 C40 H26 119.3 . . ?
C46 C41 C42 117.6(6) . . ?
C46 C41 P4 120.2(5) . . ?
C42 C41 P4 121.7(5) . . ?
C43 C42 C41 121.0(6) . . ?
C43 C42 H29 119.5 . . ?
C41 C42 H29 119.5 . . ?
C44 C43 C42 120.8(6) . . ?
C44 C43 H30 119.6 . . ?
C42 C43 H30 119.6 . . ?
C43 C44 C45 119.7(7) . . ?
C43 C44 H31 120.1 . . ?
C45 C44 H31 120.1 . . ?
C44 C45 C46 120.2(7) . . ?
C44 C45 H32 119.9 . . ?
C46 C45 H32 119.9 . . ?
C41 C46 C45 120.6(6) . . ?
C41 C46 H33 119.7 . . ?
C45 C46 H33 119.7 . . ?
C52 C47 C48 117.8(6) . . ?
C52 C47 P4 116.1(5) . . ?
C48 C47 P4 126.1(5) . . ?
C49 C48 C47 120.5(6) . . ?
C49 C48 H34 119.7 . . ?
C47 C48 H34 119.7 . . ?
C50 C49 C48 120.6(6) . . ?
C50 C49 H35 119.7 . . ?
C48 C49 H35 119.7 . . ?
C49 C50 C51 120.5(6) . . ?
C49 C50 H36 119.7 . . ?
C51 C50 H36 119.7 . . ?
C50 C51 C52 119.7(6) . . ?
C50 C51 H37 120.2 . . ?
C52 C51 H37 120.2 . . ?
C51 C52 C47 120.9(6) . . ?
C51 C52 H38 119.6 . . ?
C47 C52 H38 119.6 . . ?
C16 C53 C54 121.2(6) . . ?
C16 C53 H40 119.4 . . ?
C54 C53 H40 119.4 . . ?
C13 C54 C53 119.6(6) . . ?
C13 C54 H39 120.2 . . ?
C53 C54 H39 120.2 . . ?
C1M O1M H1M 106.8(10) . . ?
O1M C1M H1MA 109.5 . . ?
O1M C1M H1MB 109.5 . . ?
H1MA C1M H1MB 109.5 . . ?
O1M C1M H1MC 109.5 . . ?
H1MA C1M H1MC 109.5 . . ?
H1MB C1M H1MC 109.5 . . ?
C2M O2M H2M 111.3(11) . . ?
O2M C2M H2MA 109.5 . . ?
O2M C2M H2MB 109.5 . . ?
H2MA C2M H2MB 109.5 . . ?
O2M C2M H2MC 109.5 . . ?
H2MA C2M H2MC 109.5 . . ?
H2MB C2M H2MC 109.5 . . ?
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 C16 1.814(6) . ?
P1 C4 1.818(6) . ?
P1 C5 1.831(6) . ?
P2 C8 1.833(6) . ?
P2 C33 1.829(6) . ?
P2 C9 1.839(7) . ?
P3 C21 1.823(6) . ?
P3 C27 1.821(6) . ?
P3 C20 1.842(6) . ?
P4 C47 1.811(6) . ?
P4 C19 1.831(6) . ?
P4 C41 1.834(6) . ?
N5 C6 1.331(7) . ?
N5 C5 1.341(7) . ?
N6 C20 1.347(7) . ?
N6 C8 1.343(7) . ?
N1 C7 1.338(7) . ?
N1 C8 1.347(7) . ?
N2 C5 1.343(7) . ?
N2 C19 1.348(7) . ?
N3 C6 1.340(7) . ?
N3 C19 1.345(7) . ?
N4 C7 1.325(7) . ?
N4 C20 1.333(7) . ?
C1 C2 1.368(10) . ?
C1 C17 1.366(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(9) . ?
C2 H9 0.9500 . ?
C3 C4 1.374(8) . ?
C3 H6 0.9500 . ?
C4 C18 1.397(8) . ?
C6 C7 1.494(8) . ?
C9 C40 1.387(9) . ?
C9 C10 1.395(8) . ?
C10 C11 1.375(9) . ?
C10 H28 0.9500 . ?
C11 C12 1.375(10) . ?
C11 H27 0.9500 . ?
C12 C39 1.361(10) . ?
C12 H2 0.9500 . ?
C13 C54 1.378(9) . ?
C13 C14 1.377(9) . ?
C13 H3 0.9500 . ?
C14 C15 1.395(8) . ?
C14 H4 0.9500 . ?
C15 C16 1.401(8) . ?
C15 H5 0.9500 . ?
C16 C53 1.387(8) . ?
C17 C18 1.381(10) . ?
C17 H7 0.9500 . ?
C18 H8 0.9500 . ?
C21 C22 1.382(8) . ?
C21 C26 1.383(9) . ?
C22 C23 1.375(9) . ?
C22 H10 0.9500 . ?
C23 C24 1.362(10) . ?
C23 H11 0.9500 . ?
C24 C25 1.372(10) . ?
C24 H12 0.9500 . ?
C25 C26 1.398(10) . ?
C25 H14 0.9500 . ?
C26 H13 0.9500 . ?
C27 C32 1.369(8) . ?
C27 C28 1.401(8) . ?
C28 C29 1.395(9) . ?
C28 H15 0.9500 . ?
C29 C30 1.381(9) . ?
C29 H19 0.9500 . ?
C30 C31 1.372(9) . ?
C30 H16 0.9500 . ?
C31 C32 1.383(9) . ?
C31 H17 0.9500 . ?
C32 H18 0.9500 . ?
C33 C34 1.384(8) . ?
C33 C38 1.400(8) . ?
C34 C35 1.382(9) . ?
C34 H20 0.9500 . ?
C35 C36 1.361(10) . ?
C35 H24 0.9500 . ?
C36 C37 1.346(9) . ?
C36 H21 0.9500 . ?
C37 C38 1.391(9) . ?
C37 H22 0.9500 . ?
C38 H23 0.9500 . ?
C39 C40 1.387(9) . ?
C39 H25 0.9500 . ?
C40 H26 0.9500 . ?
C41 C46 1.395(8) . ?
C41 C42 1.392(8) . ?
C42 C43 1.382(9) . ?
C42 H29 0.9500 . ?
C43 C44 1.364(9) . ?
C43 H30 0.9500 . ?
C44 C45 1.373(9) . ?
C44 H31 0.9500 . ?
C45 C46 1.397(9) . ?
C45 H32 0.9500 . ?
C46 H33 0.9500 . ?
C47 C52 1.397(8) . ?
C47 C48 1.401(8) . ?
C48 C49 1.382(9) . ?
C48 H34 0.9500 . ?
C49 C50 1.366(9) . ?
C49 H35 0.9500 . ?
C50 C51 1.373(9) . ?
C50 H36 0.9500 . ?
C51 C52 1.391(9) . ?
C51 H37 0.9500 . ?
C52 H38 0.9500 . ?
C53 C54 1.393(9) . ?
C53 H40 0.9500 . ?
C54 H39 0.9500 . ?
O1M C1M 1.425(9) . ?
O1M H1M 0.8400(2) . ?
C1M H1MA 0.9800 . ?
C1M H1MB 0.9800 . ?
C1M H1MC 0.9800 . ?
O2M C2M 1.481(10) . ?
O2M H2M 0.8400(2) . ?
C2M H2MA 0.9800 . ?
C2M H2MB 0.9800 . ?
C2M H2MC 0.9800 . ?
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
C17 C1 C2 C3 0.1(11) . . . . ?
C1 C2 C3 C4 -0.3(10) . . . . ?
C2 C3 C4 C18 0.2(9) . . . . ?
C2 C3 C4 P1 174.4(5) . . . . ?
C16 P1 C4 C3 11.1(6) . . . . ?
C5 P1 C4 C3 114.0(5) . . . . ?
C16 P1 C4 C18 -174.8(5) . . . . ?
C5 P1 C4 C18 -71.8(5) . . . . ?
C6 N5 C5 N2 3.0(7) . . . . ?
C6 N5 C5 P1 176.7(4) . . . . ?
C19 N2 C5 N5 -1.6(8) . . . . ?
C19 N2 C5 P1 -175.7(4) . . . . ?
C16 P1 C5 N5 126.0(4) . . . . ?
C4 P1 C5 N5 17.2(5) . . . . ?
C16 P1 C5 N2 -59.6(4) . . . . ?
C4 P1 C5 N2 -168.5(4) . . . . ?
C5 N5 C6 N3 -2.0(8) . . . . ?
C5 N5 C6 C7 178.9(5) . . . . ?
C19 N3 C6 N5 -0.5(8) . . . . ?
C19 N3 C6 C7 178.6(5) . . . . ?
C20 N4 C7 N1 1.1(8) . . . . ?
C20 N4 C7 C6 179.6(4) . . . . ?
C8 N1 C7 N4 -2.2(8) . . . . ?
C8 N1 C7 C6 179.3(4) . . . . ?
N5 C6 C7 N4 56.6(6) . . . . ?
N3 C6 C7 N4 -122.6(5) . . . . ?
N5 C6 C7 N1 -124.8(5) . . . . ?
N3 C6 C7 N1 56.0(6) . . . . ?
C20 N6 C8 N1 -1.2(7) . . . . ?
C20 N6 C8 P2 172.4(4) . . . . ?
C7 N1 C8 N6 2.2(7) . . . . ?
C7 N1 C8 P2 -171.0(4) . . . . ?
C33 P2 C8 N6 176.7(4) . . . . ?
C9 P2 C8 N6 69.0(4) . . . . ?
C33 P2 C8 N1 -9.4(5) . . . . ?
C9 P2 C8 N1 -117.2(5) . . . . ?
C8 P2 C9 C40 144.5(5) . . . . ?
C33 P2 C9 C40 37.3(6) . . . . ?
C8 P2 C9 C10 -43.8(6) . . . . ?
C33 P2 C9 C10 -151.0(5) . . . . ?
C40 C9 C10 C11 -2.0(9) . . . . ?
P2 C9 C10 C11 -173.8(5) . . . . ?
C9 C10 C11 C12 0.6(10) . . . . ?
C10 C11 C12 C39 -0.4(11) . . . . ?
C54 C13 C14 C15 0.8(10) . . . . ?
C13 C14 C15 C16 -0.9(9) . . . . ?
C14 C15 C16 C53 0.7(8) . . . . ?
C14 C15 C16 P1 176.9(4) . . . . ?
C4 P1 C16 C53 -123.3(5) . . . . ?
C5 P1 C16 C53 130.4(5) . . . . ?
C4 P1 C16 C15 60.5(5) . . . . ?
C5 P1 C16 C15 -45.8(5) . . . . ?
C2 C1 C17 C18 0.2(12) . . . . ?
C1 C17 C18 C4 -0.4(12) . . . . ?
C3 C4 C18 C17 0.1(10) . . . . ?
P1 C4 C18 C17 -174.5(6) . . . . ?
C6 N3 C19 N2 2.2(8) . . . . ?
C6 N3 C19 P4 -170.8(4) . . . . ?
C5 N2 C19 N3 -1.3(8) . . . . ?
C5 N2 C19 P4 172.1(4) . . . . ?
C47 P4 C19 N3 -5.3(5) . . . . ?
C41 P4 C19 N3 -113.6(5) . . . . ?
C47 P4 C19 N2 -178.9(4) . . . . ?
C41 P4 C19 N2 72.8(5) . . . . ?
C7 N4 C20 N6 0.2(7) . . . . ?
C7 N4 C20 P3 175.9(4) . . . . ?
C8 N6 C20 N4 -0.1(8) . . . . ?
C8 N6 C20 P3 -176.1(4) . . . . ?
C21 P3 C20 N4 17.1(5) . . . . ?
C27 P3 C20 N4 126.3(4) . . . . ?
C21 P3 C20 N6 -166.8(4) . . . . ?
C27 P3 C20 N6 -57.6(4) . . . . ?
C27 P3 C21 C22 10.6(6) . . . . ?
C20 P3 C21 C22 115.1(5) . . . . ?
C27 P3 C21 C26 -175.7(5) . . . . ?
C20 P3 C21 C26 -71.1(5) . . . . ?
C26 C21 C22 C23 1.2(9) . . . . ?
P3 C21 C22 C23 174.9(5) . . . . ?
C21 C22 C23 C24 -0.9(10) . . . . ?
C22 C23 C24 C25 0.7(11) . . . . ?
C23 C24 C25 C26 -0.8(11) . . . . ?
C22 C21 C26 C25 -1.3(10) . . . . ?
P3 C21 C26 C25 -175.5(5) . . . . ?
C24 C25 C26 C21 1.2(11) . . . . ?
C21 P3 C27 C32 -122.1(5) . . . . ?
C20 P3 C27 C32 131.8(5) . . . . ?
C21 P3 C27 C28 61.1(5) . . . . ?
C20 P3 C27 C28 -44.9(5) . . . . ?
C32 C27 C28 C29 0.8(9) . . . . ?
P3 C27 C28 C29 177.5(5) . . . . ?
C27 C28 C29 C30 -0.5(9) . . . . ?
C28 C29 C30 C31 -0.5(10) . . . . ?
C29 C30 C31 C32 1.2(10) . . . . ?
C28 C27 C32 C31 -0.1(9) . . . . ?
P3 C27 C32 C31 -177.0(5) . . . . ?
C30 C31 C32 C27 -0.9(10) . . . . ?
C8 P2 C33 C34 118.0(5) . . . . ?
C9 P2 C33 C34 -136.1(5) . . . . ?
C8 P2 C33 C38 -63.2(6) . . . . ?
C9 P2 C33 C38 42.7(6) . . . . ?
C38 C33 C34 C35 0.8(9) . . . . ?
P2 C33 C34 C35 179.7(5) . . . . ?
C33 C34 C35 C36 -0.6(11) . . . . ?
C34 C35 C36 C37 0.9(12) . . . . ?
C35 C36 C37 C38 -1.3(11) . . . . ?
C36 C37 C38 C33 1.4(11) . . . . ?
C34 C33 C38 C37 -1.2(9) . . . . ?
P2 C33 C38 C37 -179.9(5) . . . . ?
C11 C12 C39 C40 1.6(11) . . . . ?
C12 C39 C40 C9 -3.1(11) . . . . ?
C10 C9 C40 C39 3.3(10) . . . . ?
P2 C9 C40 C39 175.4(6) . . . . ?
C47 P4 C41 C46 33.1(5) . . . . ?
C19 P4 C41 C46 139.8(5) . . . . ?
C47 P4 C41 C42 -154.7(5) . . . . ?
C19 P4 C41 C42 -48.0(5) . . . . ?
C46 C41 C42 C43 -1.0(9) . . . . ?
P4 C41 C42 C43 -173.4(5) . . . . ?
C41 C42 C43 C44 0.1(10) . . . . ?
C42 C43 C44 C45 -0.3(11) . . . . ?
C43 C44 C45 C46 1.3(11) . . . . ?
C42 C41 C46 C45 2.0(9) . . . . ?
P4 C41 C46 C45 174.5(5) . . . . ?
C44 C45 C46 C41 -2.2(10) . . . . ?
C19 P4 C47 C52 123.7(5) . . . . ?
C41 P4 C47 C52 -130.8(5) . . . . ?
C19 P4 C47 C48 -55.4(6) . . . . ?
C41 P4 C47 C48 50.1(6) . . . . ?
C52 C47 C48 C49 0.1(9) . . . . ?
P4 C47 C48 C49 179.2(5) . . . . ?
C47 C48 C49 C50 0.7(10) . . . . ?
C48 C49 C50 C51 -1.1(11) . . . . ?
C49 C50 C51 C52 0.7(11) . . . . ?
C50 C51 C52 C47 0.1(10) . . . . ?
C48 C47 C52 C51 -0.5(9) . . . . ?
P4 C47 C52 C51 -179.7(5) . . . . ?
C15 C16 C53 C54 -0.6(9) . . . . ?
P1 C16 C53 C54 -176.9(5) . . . . ?
C14 C13 C54 C53 -0.6(10) . . . . ?
C16 C53 C54 C13 0.5(9) . . . . ?
