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#$Date: 2025-08-04 17:59:17 +0300 (Mon, 04 Aug 2025) $
#$Revision: 301446 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/92/7719208.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_7719208
loop_
_publ_author_name
'Laprade, Matthew J. J.'
'Robertson, Katherine N.'
'Clyburne, Jason A. C.'
'Kozak, Christopher M.'
_publ_section_title
;
 A new class of ligand derived from the reactions of
 bis(dialkylphosphino)amines and 9-diazofluorene: preparation, structure
 and reactivity.
;
_journal_issue                   29
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11382
_journal_page_last               11397
_journal_paper_doi               10.1039/d4dt03402c
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C50 H37 N5 P2, C H2 Cl2'
_chemical_formula_sum            'C51 H39 Cl2 N5 P2'
_chemical_formula_weight         854.71
_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
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-05-03 deposited with the CCDC.	2025-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                96.9450(10)
_cell_angle_beta                 91.3780(10)
_cell_angle_gamma                111.0640(10)
_cell_formula_units_Z            2
_cell_length_a                   10.4341(10)
_cell_length_b                   11.7915(12)
_cell_length_c                   18.6856(18)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.71
_cell_measurement_theta_min      2.20
_cell_volume                     2123.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25945
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.885
_diffrn_reflns_theta_min         1.101
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         10242
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²+0.9147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7555
_reflns_number_total             10242
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt03402c2.cif
_cod_data_source_block           Compound1b_CMJL017
_cod_database_code               7719208
_shelx_shelxl_version_number     2019/3
_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   0.899
_shelx_estimated_absorpt_t_max   0.973
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
C51A C 0.3321(10) 0.1393(12) 0.4274(5) 0.037(2) Uani 0.534(3) 1 d D . P A 1
H51A H 0.366052 0.216603 0.406019 0.045 Uiso 0.534(3) 1 calc R U P A 1
H51B H 0.398131 0.097193 0.418379 0.045 Uiso 0.534(3) 1 calc R U P A 1
Cl1A Cl 0.1708(4) 0.0457(3) 0.3850(2) 0.0254(6) Uani 0.534(3) 1 d D U P A 1
Cl2A Cl 0.3261(7) 0.1740(5) 0.5213(3) 0.0685(14) Uani 0.534(3) 1 d D U P A 1
C51B C 0.3256(12) 0.0904(9) 0.4354(6) 0.051(3) Uani 0.327(3) 1 d D . P B 2
H51C H 0.394220 0.135164 0.403194 0.061 Uiso 0.327(3) 1 calc R U P B 2
H51D H 0.347278 0.018978 0.446494 0.061 Uiso 0.327(3) 1 calc R U P B 2
Cl1B Cl 0.1602(10) 0.0405(9) 0.3926(5) 0.064(2) Uani 0.327(3) 1 d D U P B 2
Cl2B Cl 0.3326(12) 0.1880(9) 0.5162(5) 0.077(2) Uani 0.327(3) 1 d D U P B 2
C51C C 0.358(3) 0.161(5) 0.4202(15) 0.034(7) Uani 0.139(3) 1 d D . P C 3
H51E H 0.361543 0.246341 0.424991 0.040 Uiso 0.139(3) 1 calc R U P C 3
H51F H 0.429379 0.154434 0.387782 0.040 Uiso 0.139(3) 1 calc R U P C 3
Cl1C Cl 0.1973(16) 0.0641(17) 0.3799(10) 0.061(3) Uani 0.139(3) 1 d D U P C 3
Cl2C Cl 0.3978(12) 0.1294(8) 0.5056(5) 0.102(3) Uani 0.139(3) 1 d D U P C 3
P1 P 0.60774(5) 0.45160(4) 0.28515(2) 0.02085(10) Uani 1 1 d . . . . .
P2 P 0.71283(5) 0.26336(4) 0.31554(3) 0.02148(11) Uani 1 1 d . . . . .
N1 N 0.70405(15) 0.39739(13) 0.32273(8) 0.0238(3) Uani 1 1 d . . . . .
N2 N 0.56751(16) 0.38931(14) 0.19844(8) 0.0247(3) Uani 1 1 d . . . . .
H2N H 0.548(2) 0.307(2) 0.1900(12) 0.040(6) Uiso 1 1 d . . . . .
N3 N 0.48479(15) 0.43640(13) 0.16120(8) 0.0231(3) Uani 1 1 d . . . . .
N4 N 0.57597(15) 0.13889(14) 0.30772(8) 0.0265(3) Uani 1 1 d . . . . .
N5 N 0.48932(15) 0.12842(13) 0.24885(8) 0.0254(3) Uani 1 1 d . . . . .
C1 C 0.69699(18) 0.61286(16) 0.28440(9) 0.0224(4) Uani 1 1 d . . . . .
C2 C 0.62639(19) 0.69075(17) 0.27461(10) 0.0267(4) Uani 1 1 d . . . . .
H2 H 0.528582 0.659424 0.269880 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6994(2) 0.81437(17) 0.27179(10) 0.0295(4) Uani 1 1 d . . . . .
H3 H 0.651141 0.867726 0.265952 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8414(2) 0.86012(17) 0.27742(10) 0.0305(4) Uani 1 1 d . . . . .
H4 H 0.890640 0.944411 0.274474 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9122(2) 0.78329(17) 0.28736(11) 0.0325(4) Uani 1 1 d . . . . .
H5 H 1.010045 0.814938 0.291331 0.039 Uiso 1 1 calc R U . . .
C6 C 0.84054(19) 0.66033(17) 0.29152(11) 0.0290(4) Uani 1 1 d . . . . .
H6 H 0.889358 0.608125 0.299243 0.035 Uiso 1 1 calc R U . . .
C7 C 0.45162(18) 0.43344(16) 0.32901(10) 0.0236(4) Uani 1 1 d . . . . .
C8 C 0.32525(19) 0.34710(18) 0.29963(11) 0.0318(4) Uani 1 1 d . . . . .
H8 H 0.318719 0.300611 0.253557 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2087(2) 0.32934(19) 0.33812(13) 0.0396(5) Uani 1 1 d . . . . .
H9 H 0.122418 0.270591 0.318184 0.048 Uiso 1 1 calc R U . . .
C10 C 0.2177(2) 0.3964(2) 0.40493(13) 0.0414(5) Uani 1 1 d . . . . .
H10 H 0.137871 0.383529 0.431072 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3428(2) 0.4825(2) 0.43402(12) 0.0399(5) Uani 1 1 d . . . . .
H11 H 0.348680 0.528856 0.480076 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4597(2) 0.50150(18) 0.39626(10) 0.0312(4) Uani 1 1 d . . . . .
H12 H 0.545474 0.561039 0.416330 0.037 Uiso 1 1 calc R U . . .
C13 C 0.44716(17) 0.39203(15) 0.09448(9) 0.0218(4) Uani 1 1 d . . . . .
C14 C 0.47590(18) 0.29863(15) 0.04358(10) 0.0235(4) Uani 1 1 d . . . . .
C15 C 0.56318(19) 0.23371(16) 0.04967(10) 0.0280(4) Uani 1 1 d . . . . .
H15 H 0.616310 0.243846 0.093609 0.034 Uiso 1 1 calc R U . . .
C16 C 0.5710(2) 0.15364(17) -0.00997(11) 0.0325(4) Uani 1 1 d . . . . .
H16 H 0.630673 0.109417 -0.006705 0.039 Uiso 1 1 calc R U . . .
C17 C 0.4929(2) 0.13789(18) -0.07375(11) 0.0362(5) Uani 1 1 d . . . . .
H17 H 0.497931 0.081320 -0.113347 0.043 Uiso 1 1 calc R U . . .
C18 C 0.4072(2) 0.20346(18) -0.08093(11) 0.0322(4) Uani 1 1 d . . . . .
H18 H 0.354584 0.192715 -0.125111 0.039 Uiso 1 1 calc R U . . .
C19 C 0.39996(18) 0.28473(16) -0.02253(10) 0.0248(4) Uani 1 1 d . . . . .
C20 C 0.32420(17) 0.36894(16) -0.01633(10) 0.0241(4) Uani 1 1 d . . . . .
C21 C 0.24000(19) 0.39263(18) -0.06627(11) 0.0309(4) Uani 1 1 d . . . . .
H21 H 0.221287 0.349928 -0.114096 0.037 Uiso 1 1 calc R U . . .
C22 C 0.18365(19) 0.48053(19) -0.04454(12) 0.0344(5) Uani 1 1 d . . . . .
H22 H 0.125592 0.497894 -0.078037 0.041 Uiso 1 1 calc R U . . .
C23 C 0.21072(19) 0.54337(18) 0.02524(12) 0.0322(4) Uani 1 1 d . . . . .
H23 H 0.169721 0.602007 0.039079 0.039 Uiso 1 1 calc R U . . .
C24 C 0.29707(18) 0.52151(16) 0.07508(10) 0.0264(4) Uani 1 1 d . . . . .
H24 H 0.317144 0.565589 0.122563 0.032 Uiso 1 1 calc R U . . .
C25 C 0.35303(17) 0.43387(15) 0.05375(10) 0.0232(4) Uani 1 1 d . . . . .
C26 C 0.82304(18) 0.25498(16) 0.24286(9) 0.0222(4) Uani 1 1 d . . . . .
C27 C 0.9342(2) 0.35759(18) 0.23141(12) 0.0365(5) Uani 1 1 d . . . . .
H27 H 0.950630 0.433862 0.260644 0.044 Uiso 1 1 calc R U . . .
C28 C 1.0214(2) 0.35042(19) 0.17805(12) 0.0423(5) Uani 1 1 d . . . . .
H28 H 1.097175 0.421628 0.170948 0.051 Uiso 1 1 calc R U . . .
C29 C 0.9995(2) 0.2423(2) 0.13572(13) 0.0480(6) Uani 1 1 d . . . . .
H29 H 1.060464 0.237403 0.099528 0.058 Uiso 1 1 calc R U . . .
C30 C 0.8886(3) 0.1398(2) 0.14554(16) 0.0702(9) Uani 1 1 d . . . . .
H30 H 0.871812 0.064515 0.115213 0.084 Uiso 1 1 calc R U . . .
C31 C 0.8008(2) 0.14561(19) 0.19942(13) 0.0475(6) Uani 1 1 d . . . . .
H31 H 0.725380 0.074038 0.206341 0.057 Uiso 1 1 calc R U . . .
C32 C 0.80106(17) 0.25568(16) 0.39725(9) 0.0229(4) Uani 1 1 d . . . . .
C33 C 0.8298(2) 0.15100(17) 0.40500(11) 0.0323(4) Uani 1 1 d . . . . .
H33 H 0.804379 0.084777 0.366559 0.039 Uiso 1 1 calc R U . . .
C34 C 0.8953(2) 0.14316(19) 0.46869(12) 0.0376(5) Uani 1 1 d . . . . .
H34 H 0.915873 0.072135 0.473523 0.045 Uiso 1 1 calc R U . . .
C35 C 0.9304(2) 0.2382(2) 0.52485(11) 0.0370(5) Uani 1 1 d . . . . .
H35 H 0.974037 0.232150 0.568680 0.044 Uiso 1 1 calc R U . . .
C36 C 0.9024(2) 0.34218(19) 0.51768(11) 0.0345(5) Uani 1 1 d . . . . .
H36 H 0.926729 0.407504 0.556626 0.041 Uiso 1 1 calc R U . . .
C37 C 0.83893(19) 0.35175(17) 0.45378(10) 0.0278(4) Uani 1 1 d . . . . .
H37 H 0.821373 0.424165 0.448752 0.033 Uiso 1 1 calc R U . . .
C38 C 0.38806(18) 0.02160(16) 0.23472(10) 0.0238(4) Uani 1 1 d . . . . .
C39 C 0.35700(18) -0.09237(16) 0.26766(10) 0.0245(4) Uani 1 1 d . . . . .
C40 C 0.4130(2) -0.11915(17) 0.32854(11) 0.0293(4) Uani 1 1 d . . . . .
H40 H 0.487197 -0.057734 0.357719 0.035 Uiso 1 1 calc R U . . .
C41 C 0.3582(2) -0.23788(19) 0.34603(12) 0.0347(5) Uani 1 1 d . . . . .
H41 H 0.394649 -0.256713 0.388155 0.042 Uiso 1 1 calc R U . . .
C42 C 0.2512(2) -0.32958(18) 0.30323(12) 0.0358(5) Uani 1 1 d . . . . .
H42 H 0.216843 -0.410274 0.315842 0.043 Uiso 1 1 calc R U . . .
C43 C 0.1947(2) -0.30385(17) 0.24250(11) 0.0317(4) Uani 1 1 d . . . . .
H43 H 0.122042 -0.366414 0.212991 0.038 Uiso 1 1 calc R U . . .
C44 C 0.24572(18) -0.18497(16) 0.22519(10) 0.0253(4) Uani 1 1 d . . . . .
C45 C 0.20167(18) -0.13166(16) 0.16701(10) 0.0258(4) Uani 1 1 d . . . . .
C46 C 0.0966(2) -0.18285(18) 0.11308(11) 0.0342(5) Uani 1 1 d . . . . .
H46 H 0.039556 -0.267138 0.109140 0.041 Uiso 1 1 calc R U . . .
C47 C 0.0753(2) -0.1103(2) 0.06499(12) 0.0410(5) Uani 1 1 d . . . . .
H47 H 0.003561 -0.145075 0.027567 0.049 Uiso 1 1 calc R U . . .
C48 C 0.1576(2) 0.0127(2) 0.07073(12) 0.0385(5) Uani 1 1 d . . . . .
H48 H 0.142299 0.061189 0.036798 0.050 Uiso 1 1 calc R U . . .
C49 C 0.2620(2) 0.06615(18) 0.12534(11) 0.0311(4) Uani 1 1 d . . . . .
H49 H 0.316748 0.151053 0.129642 0.040 Uiso 1 1 calc R U . . .
C50 C 0.28523(17) -0.00638(16) 0.17372(10) 0.0238(4) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
Cl1A C51A Cl2A 112.3(6) . . ?
Cl1A C51A H51A 109.1 . . ?
Cl2A C51A H51A 109.1 . . ?
Cl1A C51A H51B 109.1 . . ?
Cl2A C51A H51B 109.1 . . ?
H51A C51A H51B 107.9 . . ?
Cl1B C51B Cl2B 108.9(8) . . ?
Cl1B C51B H51C 109.9 . . ?
Cl2B C51B H51C 109.9 . . ?
Cl1B C51B H51D 109.9 . . ?
Cl2B C51B H51D 109.9 . . ?
H51C C51B H51D 108.3 . . ?
Cl1C C51C Cl2C 114.7(15) . . ?
Cl1C C51C H51E 108.6 . . ?
Cl2C C51C H51E 108.6 . . ?
Cl1C C51C H51F 108.6 . . ?
Cl2C C51C H51F 108.6 . . ?
H51E C51C H51F 107.6 . . ?
N1 P1 N2 111.00(8) . . ?
N1 P1 C1 109.58(8) . . ?
N2 P1 C1 105.96(8) . . ?
N1 P1 C7 113.75(8) . . ?
N2 P1 C7 108.90(8) . . ?
C1 P1 C7 107.30(8) . . ?
N1 P2 N4 122.14(8) . . ?
N1 P2 C32 106.93(8) . . ?
N4 P2 C32 102.69(8) . . ?
N1 P2 C26 106.86(8) . . ?
N4 P2 C26 110.36(8) . . ?
C32 P2 C26 106.86(8) . . ?
P1 N1 P2 133.38(10) . . ?
N3 N2 P1 113.86(12) . . ?
N3 N2 H2N 117.8(14) . . ?
P1 N2 H2N 114.9(14) . . ?
C13 N3 N2 117.89(15) . . ?
N5 N4 P2 112.51(11) . . ?
C38 N5 N4 114.27(15) . . ?
C2 C1 C6 119.40(17) . . ?
C2 C1 P1 121.53(14) . . ?
C6 C1 P1 119.04(13) . . ?
C3 C2 C1 119.83(17) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.42(17) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.05(18) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.04(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.24(17) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C12 C7 C8 119.66(17) . . ?
C12 C7 P1 118.64(14) . . ?
C8 C7 P1 121.54(14) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.08(19) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
N3 C13 C25 119.97(16) . . ?
N3 C13 C14 133.70(17) . . ?
C25 C13 C14 106.32(15) . . ?
C15 C14 C19 120.00(16) . . ?
C15 C14 C13 132.45(17) . . ?
C19 C14 C13 107.47(15) . . ?
C16 C15 C14 118.75(18) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C17 C16 C15 120.75(18) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 121.08(18) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 118.84(19) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C14 120.53(17) . . ?
C18 C19 C20 130.15(18) . . ?
C14 C19 C20 109.30(15) . . ?
C21 C20 C25 120.45(17) . . ?
C21 C20 C19 131.44(17) . . ?
C25 C20 C19 108.08(15) . . ?
C20 C21 C22 118.26(18) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C23 C22 C21 121.16(18) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 120.76(18) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 118.25(18) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C24 C25 C20 121.10(17) . . ?
C24 C25 C13 130.10(17) . . ?
C20 C25 C13 108.80(15) . . ?
C31 C26 C27 118.47(17) . . ?
C31 C26 P2 120.79(14) . . ?
C27 C26 P2 120.71(14) . . ?
C28 C27 C26 120.87(18) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C29 C28 C27 120.4(2) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 119.6(2) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C29 C30 C31 120.5(2) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C26 C31 C30 120.1(2) . . ?
C26 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C37 C32 C33 119.26(17) . . ?
C37 C32 P2 120.89(14) . . ?
C33 C32 P2 119.83(14) . . ?
C34 C33 C32 120.22(18) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C35 C34 C33 120.03(19) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 120.16(19) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C37 120.25(19) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C32 C37 C36 120.06(17) . . ?
C32 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
N5 C38 C50 121.94(16) . . ?
N5 C38 C39 131.27(17) . . ?
C50 C38 C39 106.62(15) . . ?
C40 C39 C44 119.81(17) . . ?
C40 C39 C38 132.65(17) . . ?
C44 C39 C38 107.53(16) . . ?
C39 C40 C41 118.63(18) . . ?
C39 C40 H40 120.7 . . ?
C41 C40 H40 120.7 . . ?
C42 C41 C40 121.51(19) . . ?
C42 C41 H41 119.2 . . ?
C40 C41 H41 119.2 . . ?
C43 C42 C41 120.30(18) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C42 C43 C44 119.02(19) . . ?
C42 C43 H43 120.5 . . ?
C44 C43 H43 120.5 . . ?
C43 C44 C39 120.69(18) . . ?
C43 C44 C45 130.43(18) . . ?
C39 C44 C45 108.88(15) . . ?
C46 C45 C50 120.58(17) . . ?
C46 C45 C44 131.05(17) . . ?
C50 C45 C44 108.34(16) . . ?
C47 C46 C45 119.28(19) . . ?
C47 C46 H46 120.4 . . ?
C45 C46 H46 120.4 . . ?
C46 C47 C48 120.60(19) . . ?
C46 C47 H47 119.7 . . ?
C48 C47 H47 119.7 . . ?
C47 C48 C49 120.9(2) . . ?
C47 C48 H48 119.6 . . ?
C49 C48 H48 119.6 . . ?
C48 C49 C50 119.00(18) . . ?
C48 C49 H49 120.5 . . ?
C50 C49 H49 120.5 . . ?
C49 C50 C45 119.62(17) . . ?
C49 C50 C38 131.84(17) . . ?
C45 C50 C38 108.53(15) . . ?
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
C51A Cl1A 1.751(8) . ?
C51A Cl2A 1.761(10) . ?
C51A H51A 0.9900 . ?
C51A H51B 0.9900 . ?
C51B Cl1B 1.747(11) . ?
C51B Cl2B 1.767(11) . ?
C51B H51C 0.9900 . ?
C51B H51D 0.9900 . ?
C51C Cl1C 1.742(16) . ?
C51C Cl2C 1.755(17) . ?
C51C H51E 0.9900 . ?
C51C H51F 0.9900 . ?
P1 N1 1.5646(15) . ?
P1 N2 1.6728(16) . ?
P1 C1 1.7937(18) . ?
P1 C7 1.7965(18) . ?
P2 N1 1.6054(15) . ?
P2 N4 1.6267(15) . ?
P2 C32 1.7924(18) . ?
P2 C26 1.8169(18) . ?
N2 N3 1.395(2) . ?
N2 H2N 0.91(2) . ?
N3 C13 1.286(2) . ?
N4 N5 1.372(2) . ?
N5 C38 1.312(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.390(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C25 1.480(2) . ?
C13 C14 1.485(2) . ?
C14 C15 1.395(2) . ?
C14 C19 1.411(2) . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.471(3) . ?
C20 C21 1.386(3) . ?
C20 C25 1.402(2) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(2) . ?
C24 H24 0.9500 . ?
C26 C31 1.378(3) . ?
C26 C27 1.386(3) . ?
C27 C28 1.381(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.357(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.375(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C37 1.387(2) . ?
C32 C33 1.393(3) . ?
C33 C34 1.387(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.376(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.388(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C50 1.468(2) . ?
C38 C39 1.479(2) . ?
C39 C40 1.387(3) . ?
C39 C44 1.416(2) . ?
C40 C41 1.392(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.391(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.381(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.391(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.462(3) . ?
C45 C46 1.381(3) . ?
C45 C50 1.408(2) . ?
C46 C47 1.379(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.384(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.386(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.390(3) . ?
C49 H49 0.9500 . ?
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
_geom_hbond_publ_flag
N2 H2N N5 0.91(2) 2.39(2) 3.154(2) 142.3(18) . yes
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
N2 P1 N1 P2 -36.36(16) . . . . ?
C1 P1 N1 P2 -153.04(13) . . . . ?
C7 P1 N1 P2 86.87(15) . . . . ?
N4 P2 N1 P1 -40.76(17) . . . . ?
C32 P2 N1 P1 -158.31(13) . . . . ?
C26 P2 N1 P1 87.55(14) . . . . ?
N1 P1 N2 N3 -178.27(11) . . . . ?
C1 P1 N2 N3 -59.39(13) . . . . ?
C7 P1 N2 N3 55.75(14) . . . . ?
P1 N2 N3 C13 -178.87(12) . . . . ?
N1 P2 N4 N5 58.09(15) . . . . ?
C32 P2 N4 N5 177.70(12) . . . . ?
C26 P2 N4 N5 -68.68(14) . . . . ?
P2 N4 N5 C38 170.74(12) . . . . ?
N1 P1 C1 C2 -160.53(14) . . . . ?
N2 P1 C1 C2 79.65(16) . . . . ?
C7 P1 C1 C2 -36.58(17) . . . . ?
N1 P1 C1 C6 21.52(17) . . . . ?
N2 P1 C1 C6 -98.30(15) . . . . ?
C7 P1 C1 C6 145.47(15) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
P1 C1 C2 C3 -177.71(14) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
P1 C1 C6 C5 176.64(15) . . . . ?
N1 P1 C7 C12 69.87(16) . . . . ?
N2 P1 C7 C12 -165.77(14) . . . . ?
C1 P1 C7 C12 -51.50(16) . . . . ?
N1 P1 C7 C8 -105.55(16) . . . . ?
N2 P1 C7 C8 18.81(17) . . . . ?
C1 P1 C7 C8 133.08(15) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
P1 C7 C8 C9 174.95(15) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C8 C7 C12 C11 0.6(3) . . . . ?
P1 C7 C12 C11 -174.91(15) . . . . ?
N2 N3 C13 C25 176.56(14) . . . . ?
N2 N3 C13 C14 -2.2(3) . . . . ?
N3 C13 C14 C15 -5.9(3) . . . . ?
C25 C13 C14 C15 175.25(18) . . . . ?
N3 C13 C14 C19 177.49(18) . . . . ?
C25 C13 C14 C19 -1.36(18) . . . . ?
C19 C14 C15 C16 -1.4(3) . . . . ?
C13 C14 C15 C16 -177.69(17) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C18 1.6(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C17 C18 C19 C20 176.70(18) . . . . ?
C15 C14 C19 C18 2.4(3) . . . . ?
C13 C14 C19 C18 179.55(16) . . . . ?
C15 C14 C19 C20 -176.02(15) . . . . ?
C13 C14 C19 C20 1.09(18) . . . . ?
C18 C19 C20 C21 -0.7(3) . . . . ?
C14 C19 C20 C21 177.59(18) . . . . ?
C18 C19 C20 C25 -178.65(18) . . . . ?
C14 C19 C20 C25 -0.38(19) . . . . ?
C25 C20 C21 C22 -1.1(3) . . . . ?
C19 C20 C21 C22 -178.82(18) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C21 C22 C23 C24 1.1(3) . . . . ?
C22 C23 C24 C25 -1.3(3) . . . . ?
C23 C24 C25 C20 0.3(2) . . . . ?
C23 C24 C25 C13 179.82(17) . . . . ?
C21 C20 C25 C24 0.9(3) . . . . ?
C19 C20 C25 C24 179.14(15) . . . . ?
C21 C20 C25 C13 -178.74(15) . . . . ?
C19 C20 C25 C13 -0.50(18) . . . . ?
N3 C13 C25 C24 2.5(3) . . . . ?
C14 C13 C25 C24 -178.45(17) . . . . ?
N3 C13 C25 C20 -177.90(15) . . . . ?
C14 C13 C25 C20 1.15(18) . . . . ?
N1 P2 C26 C31 -147.47(18) . . . . ?
N4 P2 C26 C31 -12.6(2) . . . . ?
C32 P2 C26 C31 98.33(18) . . . . ?
N1 P2 C26 C27 34.72(18) . . . . ?
N4 P2 C26 C27 169.59(16) . . . . ?
C32 P2 C26 C27 -79.47(17) . . . . ?
C31 C26 C27 C28 -0.4(3) . . . . ?
P2 C26 C27 C28 177.41(17) . . . . ?
C26 C27 C28 C29 0.1(4) . . . . ?
C27 C28 C29 C30 0.9(4) . . . . ?
C28 C29 C30 C31 -1.5(5) . . . . ?
C27 C26 C31 C30 -0.1(4) . . . . ?
P2 C26 C31 C30 -178.0(2) . . . . ?
C29 C30 C31 C26 1.1(5) . . . . ?
N1 P2 C32 C37 4.39(17) . . . . ?
N4 P2 C32 C37 -125.30(15) . . . . ?
C26 P2 C32 C37 118.54(15) . . . . ?
N1 P2 C32 C33 -176.96(14) . . . . ?
N4 P2 C32 C33 53.35(16) . . . . ?
C26 P2 C32 C33 -62.81(16) . . . . ?
C37 C32 C33 C34 0.1(3) . . . . ?
P2 C32 C33 C34 -178.56(15) . . . . ?
C32 C33 C34 C35 0.9(3) . . . . ?
C33 C34 C35 C36 -0.9(3) . . . . ?
C34 C35 C36 C37 -0.1(3) . . . . ?
C33 C32 C37 C36 -1.1(3) . . . . ?
P2 C32 C37 C36 177.52(14) . . . . ?
C35 C36 C37 C32 1.1(3) . . . . ?
N4 N5 C38 C50 -179.93(15) . . . . ?
N4 N5 C38 C39 -5.3(3) . . . . ?
N5 C38 C39 C40 9.2(3) . . . . ?
C50 C38 C39 C40 -175.49(18) . . . . ?
N5 C38 C39 C44 -172.07(18) . . . . ?
C50 C38 C39 C44 3.19(18) . . . . ?
C44 C39 C40 C41 0.5(3) . . . . ?
C38 C39 C40 C41 179.03(18) . . . . ?
C39 C40 C41 C42 1.2(3) . . . . ?
C40 C41 C42 C43 -1.2(3) . . . . ?
C41 C42 C43 C44 -0.4(3) . . . . ?
C42 C43 C44 C39 2.1(3) . . . . ?
C42 C43 C44 C45 -176.83(18) . . . . ?
C40 C39 C44 C43 -2.1(3) . . . . ?
C38 C39 C44 C43 178.98(16) . . . . ?
C40 C39 C44 C45 177.00(16) . . . . ?
C38 C39 C44 C45 -1.88(19) . . . . ?
C43 C44 C45 C46 0.7(3) . . . . ?
C39 C44 C45 C46 -178.31(19) . . . . ?
C43 C44 C45 C50 178.82(18) . . . . ?
C39 C44 C45 C50 -0.2(2) . . . . ?
C50 C45 C46 C47 0.9(3) . . . . ?
C44 C45 C46 C47 178.82(19) . . . . ?
C45 C46 C47 C48 -0.4(3) . . . . ?
C46 C47 C48 C49 -0.8(3) . . . . ?
C47 C48 C49 C50 1.4(3) . . . . ?
C48 C49 C50 C45 -0.9(3) . . . . ?
C48 C49 C50 C38 178.04(19) . . . . ?
C46 C45 C50 C49 -0.3(3) . . . . ?
C44 C45 C50 C49 -178.63(16) . . . . ?
C46 C45 C50 C38 -179.42(17) . . . . ?
C44 C45 C50 C38 2.24(19) . . . . ?
N5 C38 C50 C49 -6.5(3) . . . . ?
C39 C38 C50 C49 177.66(19) . . . . ?
N5 C38 C50 C45 172.45(16) . . . . ?
C39 C38 C50 C45 -3.35(19) . . . . ?
