#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/80/7128036.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_7128036
loop_
_publ_author_name
'Tarrieu, Robert'
'Delgado, Irene Hernandez'
'Zinna, Francesco'
'Dorcet, Vincent'
'Colombel-Rouen, Sophie'
'Crévisy, Christophe'
'Baslé, Olivier'
'Bosson, Johann'
'Lacour, Jérôme'
_publ_section_title
;
 Hybrids of cationic [4]helicene and N-heterocyclic carbene as ligands for
 complexes exhibiting (chir)optical properties in the far red spectral
 window.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3793
_journal_page_last               3796
_journal_paper_doi               10.1039/d1cc00898f
_journal_volume                  57
_journal_year                    2021
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C42 H53 N4 O2 Se, F6 P, 2(C H2 Cl2)'
_chemical_formula_sum            'C44 H57 Cl4 F6 N4 O2 P Se'
_chemical_formula_weight         1039.66
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-02-11 deposited with the CCDC.	2021-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                88.465(2)
_cell_angle_beta                 86.617(2)
_cell_angle_gamma                87.886(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8906(6)
_cell_length_b                   12.5154(9)
_cell_length_c                   19.2461(13)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.54
_cell_measurement_theta_min      2.37
_cell_measurement_wavelength     0.71073
_cell_volume                     2375.9(3)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      -0.0225580
_diffrn_orient_matrix_UB_12      0.0784742
_diffrn_orient_matrix_UB_13      -0.0029842
_diffrn_orient_matrix_UB_21      -0.0015226
_diffrn_orient_matrix_UB_22      -0.0038621
_diffrn_orient_matrix_UB_23      -0.0517773
_diffrn_orient_matrix_UB_31      -0.0987923
_diffrn_orient_matrix_UB_32      -0.0149565
_diffrn_orient_matrix_UB_33      0.0045820
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            58756
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         1.965
_exptl_absorpt_coefficient_mu    1.113
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.150
_refine_diff_density_max         1.177
_refine_diff_density_min         -1.191
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         10948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0778P)²+1.8924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1493
_reflns_number_gt                7508
_reflns_number_total             10948
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc00898f2.cif
_cod_data_source_block           DB254
_cod_depositor_comments
'Adding full bibliography for 7128035--7128036.cif.'
_cod_database_code               7128036
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
Se1 Se 0.50547(3) 0.72480(3) 0.63251(2) 0.02359(11) Uani 1 1 d . . . . .
C1 C 0.9101(3) 0.7918(3) 0.56693(18) 0.0253(7) Uani 1 1 d . . . . .
H1A H 0.948093 0.848615 0.535659 0.030 Uiso 1 1 calc R U . . .
H1B H 0.985261 0.759527 0.593068 0.030 Uiso 1 1 calc R U . . .
C2 C 0.8554(4) 0.7060(3) 0.52247(19) 0.0306(8) Uani 1 1 d . . . . .
H2A H 0.810560 0.652092 0.553594 0.037 Uiso 1 1 calc R U . . .
H2B H 0.932580 0.669445 0.496686 0.037 Uiso 1 1 calc R U . . .
C3 C 0.7545(3) 0.7487(3) 0.47024(18) 0.0290(8) Uani 1 1 d . . . . .
H3A H 0.714068 0.687338 0.448748 0.035 Uiso 1 1 calc R U . . .
H3B H 0.680446 0.789552 0.495603 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8172(3) 0.8204(3) 0.41268(18) 0.0294(8) Uani 1 1 d . . . . .
H4A H 0.865910 0.774779 0.377441 0.035 Uiso 1 1 calc R U . . .
H4B H 0.884847 0.865071 0.432866 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7149(4) 0.8938(3) 0.37636(19) 0.0326(8) Uani 1 1 d . . . . .
H5A H 0.640726 0.850210 0.361508 0.039 Uiso 1 1 calc R U . . .
H5B H 0.760229 0.925839 0.333971 0.039 Uiso 1 1 calc R U . . .
C6 C 0.6536(3) 0.9840(3) 0.4221(2) 0.0341(9) Uani 1 1 d . . . . .
H6A H 0.577755 1.019792 0.398216 0.041 Uiso 1 1 calc R U . . .
H6B H 0.615821 0.952248 0.466421 0.041 Uiso 1 1 calc R U . . .
C7 C 0.7546(3) 1.0679(3) 0.4385(2) 0.0310(8) Uani 1 1 d . . . . .
H7A H 0.842449 1.031108 0.447493 0.037 Uiso 1 1 calc R U . . .
H7B H 0.769312 1.115394 0.396982 0.037 Uiso 1 1 calc R U . . .
C8 C 0.7107(3) 1.1364(3) 0.50070(19) 0.0292(8) Uani 1 1 d . . . . .
H8A H 0.618636 1.167164 0.493958 0.035 Uiso 1 1 calc R U . . .
H8B H 0.772728 1.196475 0.502040 0.035 Uiso 1 1 calc R U . . .
C9 C 0.7094(3) 1.0755(3) 0.57106(19) 0.0280(8) Uani 1 1 d . . . . .
H9A H 0.665094 1.121926 0.607224 0.034 Uiso 1 1 calc R U . . .
H9B H 0.654100 1.011577 0.568340 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8499(3) 1.0401(3) 0.59331(19) 0.0261(7) Uani 1 1 d . . . . .
H10A H 0.905910 1.018242 0.551409 0.031 Uiso 1 1 calc R U . . .
H10B H 0.892512 1.102438 0.612516 0.031 Uiso 1 1 calc R U . . .
C11 C 0.8532(3) 0.9488(3) 0.64696(18) 0.0247(7) Uani 1 1 d . . . . .
H11A H 0.794062 0.968659 0.688264 0.030 Uiso 1 1 calc R U . . .
H11B H 0.946730 0.937883 0.662074 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8059(3) 0.8430(3) 0.61865(17) 0.0211(7) Uani 1 1 d . . . . .
H12 H 0.721389 0.859517 0.593723 0.025 Uiso 1 1 calc R U . . .
N13 N 0.7722(2) 0.7667(2) 0.67616(14) 0.0193(6) Uani 1 1 d . . . . .
C14 C 0.8597(3) 0.7341(3) 0.72664(17) 0.0245(7) Uani 1 1 d . . . . .
H14 H 0.948146 0.759125 0.731317 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7972(3) 0.6609(3) 0.76774(17) 0.0231(7) Uani 1 1 d . . . . .
H15 H 0.832904 0.624357 0.806882 0.028 Uiso 1 1 calc R U . . .
N16 N 0.6701(2) 0.6485(2) 0.74233(13) 0.0173(5) Uani 1 1 d . . . . .
C17 C 0.6542(3) 0.7142(2) 0.68549(16) 0.0162(6) Uani 1 1 d . . . . .
C18 C 0.5725(3) 0.5753(2) 0.77059(16) 0.0179(6) Uani 1 1 d . . . . .
C19 C 0.4536(3) 0.6171(2) 0.80259(16) 0.0190(6) Uani 1 1 d . . . . .
H19 H 0.437654 0.692392 0.801272 0.023 Uiso 1 1 calc R U . . .
C20 C 0.3581(3) 0.5545(2) 0.83601(16) 0.0178(6) Uani 1 1 d . . . . .
H20 H 0.275873 0.585923 0.855291 0.021 Uiso 1 1 calc R U . . .
C21 C 0.3828(3) 0.4438(2) 0.84150(15) 0.0153(6) Uani 1 1 d . . . . .
N22 N 0.2951(2) 0.3781(2) 0.87871(13) 0.0169(5) Uani 1 1 d . . . . .
C23 C 0.3064(3) 0.2683(2) 0.87336(16) 0.0188(6) Uani 1 1 d . . . . .
C24 C 0.2053(3) 0.2032(3) 0.90444(18) 0.0242(7) Uani 1 1 d . . . . .
H24 H 0.131874 0.233826 0.932068 0.029 Uiso 1 1 calc R U . . .
C25 C 0.2142(3) 0.0957(3) 0.89441(19) 0.0294(8) Uani 1 1 d . . . . .
H25 H 0.148886 0.051592 0.917794 0.035 Uiso 1 1 calc R U . . .
C26 C 0.3162(3) 0.0480(3) 0.85079(19) 0.0277(8) Uani 1 1 d . . . . .
H26 H 0.315617 -0.026173 0.841703 0.033 Uiso 1 1 calc R U . . .
C27 C 0.4167(3) 0.1096(3) 0.82149(18) 0.0226(7) Uani 1 1 d . . . . .
C28 C 0.4215(3) 0.2210(2) 0.83703(16) 0.0184(6) Uani 1 1 d . . . . .
C29 C 0.5321(3) 0.2869(2) 0.81521(15) 0.0163(6) Uani 1 1 d . . . . .
C30 C 0.5042(3) 0.3974(2) 0.80939(15) 0.0153(6) Uani 1 1 d . . . . .
C31 C 0.5967(3) 0.4648(2) 0.77029(16) 0.0162(6) Uani 1 1 d . . . . .
N32 N 0.7051(2) 0.4145(2) 0.73268(14) 0.0187(6) Uani 1 1 d . . . . .
C33 C 0.7534(3) 0.3150(2) 0.75559(17) 0.0193(7) Uani 1 1 d . . . . .
C34 C 0.8853(3) 0.2785(3) 0.73370(18) 0.0258(7) Uani 1 1 d . . . . .
H34 H 0.937964 0.318417 0.700023 0.031 Uiso 1 1 calc R U . . .
C35 C 0.9365(3) 0.1848(3) 0.76167(19) 0.0296(8) Uani 1 1 d . . . . .
H35 H 1.024302 0.159226 0.745960 0.036 Uiso 1 1 calc R U . . .
C36 C 0.8636(3) 0.1262(3) 0.81229(19) 0.0290(8) Uani 1 1 d . . . . .
H36 H 0.903369 0.063421 0.832528 0.035 Uiso 1 1 calc R U . . .
C37 C 0.7340(3) 0.1592(3) 0.83306(18) 0.0232(7) Uani 1 1 d . . . . .
C38 C 0.6714(3) 0.2510(2) 0.80078(16) 0.0182(6) Uani 1 1 d . . . . .
C39 C 0.1733(3) 0.4254(3) 0.91598(17) 0.0198(7) Uani 1 1 d . . . . .
H39A H 0.193256 0.497730 0.931347 0.024 Uiso 1 1 calc R U . . .
H39B H 0.149809 0.380897 0.957955 0.024 Uiso 1 1 calc R U . . .
C40 C 0.0534(3) 0.4331(3) 0.87000(17) 0.0229(7) Uani 1 1 d . . . . .
H40A H 0.071655 0.486587 0.832071 0.027 Uiso 1 1 calc R U . . .
H40B H 0.043372 0.363136 0.848442 0.027 Uiso 1 1 calc R U . . .
C41 C -0.0784(3) 0.4648(3) 0.90990(19) 0.0292(8) Uani 1 1 d . . . . .
H41A H -0.093586 0.415235 0.949668 0.044 Uiso 1 1 calc R U . . .
H41B H -0.153602 0.461783 0.879147 0.044 Uiso 1 1 calc R U . . .
H41C H -0.072999 0.537650 0.926643 0.044 Uiso 1 1 calc R U . . .
C42 C 0.7558(3) 0.4582(3) 0.66411(17) 0.0256(7) Uani 1 1 d . . . . .
H42A H 0.854534 0.468239 0.664914 0.031 Uiso 1 1 calc R U . . .
H42B H 0.711329 0.529159 0.655783 0.031 Uiso 1 1 calc R U . . .
C43 C 0.7293(4) 0.3857(3) 0.60475(19) 0.0316(8) Uani 1 1 d . . . . .
H43A H 0.771729 0.415362 0.560854 0.038 Uiso 1 1 calc R U . . .
H43B H 0.771829 0.314179 0.613550 0.038 Uiso 1 1 calc R U . . .
C44 C 0.5798(4) 0.3746(4) 0.5967(2) 0.0506(12) Uani 1 1 d . . . . .
H44A H 0.540053 0.335429 0.637203 0.076 Uiso 1 1 calc R U . . .
H44B H 0.566644 0.335326 0.554373 0.076 Uiso 1 1 calc R U . . .
H44C H 0.535611 0.445749 0.593254 0.076 Uiso 1 1 calc R U . . .
O45 O 0.5118(2) 0.07360(18) 0.77334(13) 0.0280(5) Uani 1 1 d . . . . .
C46 C 0.5066(4) -0.0358(3) 0.7554(2) 0.0396(10) Uani 1 1 d . . . . .
H46A H 0.527581 -0.081538 0.795718 0.059 Uiso 1 1 calc R U . . .
H46B H 0.573001 -0.050806 0.716739 0.059 Uiso 1 1 calc R U . . .
H46C H 0.415550 -0.050281 0.741293 0.059 Uiso 1 1 calc R U . . .
O47 O 0.6592(2) 0.11216(18) 0.88582(13) 0.0290(6) Uani 1 1 d . . . . .
C48 C 0.7204(4) 0.0231(3) 0.9221(2) 0.0450(11) Uani 1 1 d . . . . .
H48A H 0.745412 -0.033736 0.889272 0.067 Uiso 1 1 calc R U . . .
H48B H 0.655817 -0.003807 0.958447 0.067 Uiso 1 1 calc R U . . .
H48C H 0.801660 0.046068 0.943485 0.067 Uiso 1 1 calc R U . . .
P1 P 1.06569(10) 0.78904(7) 0.89262(6) 0.0328(2) Uani 1 1 d . . . . .
F1 F 0.9106(2) 0.7688(2) 0.90981(18) 0.0725(9) Uani 1 1 d . . . . .
F2 F 1.0684(2) 0.70195(17) 0.83299(13) 0.0434(6) Uani 1 1 d . . . . .
F3 F 1.1087(3) 0.6953(2) 0.94548(14) 0.0645(8) Uani 1 1 d . . . . .
F4 F 1.0288(3) 0.88064(18) 0.83764(14) 0.0529(7) Uani 1 1 d . . . . .
F5 F 1.0650(3) 0.8743(2) 0.95143(15) 0.0709(9) Uani 1 1 d . . . . .
F6 F 1.2231(2) 0.80675(19) 0.87379(16) 0.0584(8) Uani 1 1 d . . . . .
C101 C 0.4539(5) 0.7413(6) 0.9814(3) 0.083(2) Uani 1 1 d . . . . .
H10C H 0.451656 0.794662 1.018507 0.099 Uiso 1 1 calc R U . . .
H10D H 0.385714 0.764631 0.947960 0.099 Uiso 1 1 calc R U . . .
Cl1 Cl 0.61269(12) 0.73792(12) 0.93875(7) 0.0639(4) Uani 1 1 d . . . . .
Cl2 Cl 0.41106(17) 0.6194(2) 1.01763(7) 0.1304(10) Uani 1 1 d . . . . .
C201 C 0.2212(5) 0.5374(4) 0.6738(2) 0.0478(11) Uani 1 1 d . . . . .
H20A H 0.168350 0.576893 0.710768 0.057 Uiso 1 1 calc R U . . .
H20B H 0.313692 0.565500 0.669692 0.057 Uiso 1 1 calc R U . . .
Cl11 Cl 0.14451(19) 0.55783(13) 0.59474(8) 0.0881(5) Uani 1 1 d . . . . .
Cl12 Cl 0.23029(10) 0.40002(9) 0.69683(5) 0.0417(2) 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'
F F 0.0171 0.0103 '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'
Se Se -0.0929 2.2259 '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'
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 C12 114.9(3) . . ?
C2 C1 H1A 108.5 . . ?
C12 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
C12 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C1 C2 C3 114.2(3) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 113.8(3) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 114.2(3) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 113.7(3) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 113.9(3) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 114.4(3) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 114.2(3) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 113.8(3) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 115.4(3) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 112.7(3) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N13 C12 C1 109.9(3) . . ?
N13 C12 C11 110.7(3) . . ?
C1 C12 C11 112.7(3) . . ?
N13 C12 H12 107.8 . . ?
C1 C12 H12 107.8 . . ?
C11 C12 H12 107.8 . . ?
C17 N13 C14 110.1(3) . . ?
C17 N13 C12 125.4(3) . . ?
C14 N13 C12 124.4(3) . . ?
C15 C14 N13 107.6(3) . . ?
C15 C14 H14 126.2 . . ?
N13 C14 H14 126.2 . . ?
C14 C15 N16 107.1(3) . . ?
C14 C15 H15 126.5 . . ?
N16 C15 H15 126.5 . . ?
C17 N16 C15 110.0(2) . . ?
C17 N16 C18 125.2(2) . . ?
C15 N16 C18 124.8(3) . . ?
N13 C17 N16 105.2(2) . . ?
N13 C17 Se1 128.3(2) . . ?
N16 C17 Se1 126.4(2) . . ?
C19 C18 C31 119.7(3) . . ?
C19 C18 N16 118.1(3) . . ?
C31 C18 N16 122.2(3) . . ?
C20 C19 C18 122.9(3) . . ?
C20 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
N22 C21 C20 121.8(3) . . ?
N22 C21 C30 118.6(3) . . ?
C20 C21 C30 119.5(3) . . ?
C21 N22 C23 121.2(2) . . ?
C21 N22 C39 119.4(2) . . ?
C23 N22 C39 118.6(2) . . ?
N22 C23 C24 120.4(3) . . ?
N22 C23 C28 119.7(3) . . ?
C24 C23 C28 120.0(3) . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 122.2(3) . . ?
C24 C25 H25 118.9 . . ?
C26 C25 H25 118.9 . . ?
C27 C26 C25 119.2(3) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
O45 C27 C26 123.6(3) . . ?
O45 C27 C28 115.5(3) . . ?
C26 C27 C28 120.8(3) . . ?
C23 C28 C29 118.8(3) . . ?
C23 C28 C27 117.3(3) . . ?
C29 C28 C27 123.8(3) . . ?
C30 C29 C28 117.1(3) . . ?
C30 C29 C38 116.7(3) . . ?
C28 C29 C38 126.2(3) . . ?
C29 C30 C21 120.5(3) . . ?
C29 C30 C31 120.2(3) . . ?
C21 C30 C31 119.3(3) . . ?
C18 C31 N32 123.9(3) . . ?
C18 C31 C30 118.8(3) . . ?
N32 C31 C30 117.2(3) . . ?
C33 N32 C31 119.0(3) . . ?
C33 N32 C42 119.4(3) . . ?
C31 N32 C42 121.0(3) . . ?
N32 C33 C38 120.1(3) . . ?
N32 C33 C34 119.7(3) . . ?
C38 C33 C34 120.2(3) . . ?
C35 C34 C33 119.1(3) . . ?
C35 C34 H34 120.5 . . ?
C33 C34 H34 120.5 . . ?
C34 C35 C36 121.9(3) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C37 C36 C35 119.8(3) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
O47 C37 C36 124.0(3) . . ?
O47 C37 C38 115.6(3) . . ?
C36 C37 C38 120.4(3) . . ?
C33 C38 C37 117.7(3) . . ?
C33 C38 C29 117.7(3) . . ?
C37 C38 C29 124.5(3) . . ?
N22 C39 C40 111.4(3) . . ?
N22 C39 H39A 109.3 . . ?
C40 C39 H39A 109.3 . . ?
N22 C39 H39B 109.3 . . ?
C40 C39 H39B 109.3 . . ?
H39A C39 H39B 108.0 . . ?
C41 C40 C39 112.7(3) . . ?
C41 C40 H40A 109.1 . . ?
C39 C40 H40A 109.1 . . ?
C41 C40 H40B 109.1 . . ?
C39 C40 H40B 109.1 . . ?
H40A C40 H40B 107.8 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N32 C42 C43 112.5(3) . . ?
N32 C42 H42A 109.1 . . ?
C43 C42 H42A 109.1 . . ?
N32 C42 H42B 109.1 . . ?
C43 C42 H42B 109.1 . . ?
H42A C42 H42B 107.8 . . ?
C44 C43 C42 111.9(3) . . ?
C44 C43 H43A 109.2 . . ?
C42 C43 H43A 109.2 . . ?
C44 C43 H43B 109.2 . . ?
C42 C43 H43B 109.2 . . ?
H43A C43 H43B 107.9 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C27 O45 C46 116.6(3) . . ?
O45 C46 H46A 109.5 . . ?
O45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C37 O47 C48 117.6(3) . . ?
O47 C48 H48A 109.5 . . ?
O47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
O47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
F5 P1 F1 91.08(17) . . ?
F5 P1 F4 90.14(15) . . ?
F1 P1 F4 90.84(16) . . ?
F5 P1 F3 91.48(16) . . ?
F1 P1 F3 91.29(17) . . ?
F4 P1 F3 177.30(17) . . ?
F5 P1 F6 90.50(17) . . ?
F1 P1 F6 178.40(17) . . ?
F4 P1 F6 89.41(14) . . ?
F3 P1 F6 88.41(15) . . ?
F5 P1 F2 179.27(16) . . ?
F1 P1 F2 89.55(14) . . ?
F4 P1 F2 90.23(13) . . ?
F3 P1 F2 88.13(14) . . ?
F6 P1 F2 88.87(14) . . ?
Cl2 C101 Cl1 112.7(3) . . ?
Cl2 C101 H10C 109.1 . . ?
Cl1 C101 H10C 109.1 . . ?
Cl2 C101 H10D 109.1 . . ?
Cl1 C101 H10D 109.1 . . ?
H10C C101 H10D 107.8 . . ?
Cl11 C201 Cl12 110.7(2) . . ?
Cl11 C201 H20A 109.5 . . ?
Cl12 C201 H20A 109.5 . . ?
Cl11 C201 H20B 109.5 . . ?
Cl12 C201 H20B 109.5 . . ?
H20A C201 H20B 108.1 . . ?
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
Se1 C17 1.837(3) . ?
C1 C2 1.524(5) . ?
C1 C12 1.526(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.530(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.525(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.528(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.535(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.527(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.524(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.535(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.520(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.544(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N13 1.474(4) . ?
C12 H12 1.0000 . ?
N13 C17 1.361(4) . ?
N13 C14 1.383(4) . ?
C14 C15 1.339(5) . ?
C14 H14 0.9500 . ?
C15 N16 1.391(4) . ?
C15 H15 0.9500 . ?
N16 C17 1.364(4) . ?
N16 C18 1.430(4) . ?
C18 C19 1.387(4) . ?
C18 C31 1.395(4) . ?
C19 C20 1.369(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.401(4) . ?
C20 H20 0.9500 . ?
C21 N22 1.375(4) . ?
C21 C30 1.428(4) . ?
N22 C23 1.380(4) . ?
N22 C39 1.477(4) . ?
C23 C24 1.409(4) . ?
C23 C28 1.419(4) . ?
C24 C25 1.363(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.401(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.366(4) . ?
C26 H26 0.9500 . ?
C27 O45 1.355(4) . ?
C27 C28 1.437(4) . ?
C28 C29 1.431(4) . ?
C29 C30 1.403(4) . ?
C29 C38 1.447(4) . ?
C30 C31 1.434(4) . ?
C31 N32 1.398(4) . ?
N32 C33 1.388(4) . ?
N32 C42 1.482(4) . ?
C33 C38 1.408(4) . ?
C33 C34 1.410(4) . ?
C34 C35 1.370(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.373(5) . ?
C36 H36 0.9500 . ?
C37 O47 1.355(4) . ?
C37 C38 1.429(4) . ?
C39 C40 1.520(4) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.518(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.518(5) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.508(5) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
O45 C46 1.425(4) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
O47 C48 1.433(4) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
P1 F5 1.576(3) . ?
P1 F1 1.579(3) . ?
P1 F4 1.586(2) . ?
P1 F3 1.595(3) . ?
P1 F6 1.600(2) . ?
P1 F2 1.602(2) . ?
C101 Cl2 1.717(7) . ?
C101 Cl1 1.728(5) . ?
C101 H10C 0.9900 . ?
C101 H10D 0.9900 . ?
C201 Cl11 1.749(4) . ?
C201 Cl12 1.764(5) . ?
C201 H20A 0.9900 . ?
C201 H20B 0.9900 . ?
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
C12 C1 C2 C3 67.9(4) . . . . ?
C1 C2 C3 C4 66.9(4) . . . . ?
C2 C3 C4 C5 -159.5(3) . . . . ?
C3 C4 C5 C6 70.3(4) . . . . ?
C4 C5 C6 C7 68.2(4) . . . . ?
C5 C6 C7 C8 -161.5(3) . . . . ?
C6 C7 C8 C9 69.0(4) . . . . ?
C7 C8 C9 C10 68.2(4) . . . . ?
C8 C9 C10 C11 -159.1(3) . . . . ?
C9 C10 C11 C12 65.6(4) . . . . ?
C2 C1 C12 N13 72.3(4) . . . . ?
C2 C1 C12 C11 -163.7(3) . . . . ?
C10 C11 C12 N13 -163.4(3) . . . . ?
C10 C11 C12 C1 73.0(4) . . . . ?
C1 C12 N13 C17 -106.5(3) . . . . ?
C11 C12 N13 C17 128.3(3) . . . . ?
C1 C12 N13 C14 70.0(4) . . . . ?
C11 C12 N13 C14 -55.2(4) . . . . ?
C17 N13 C14 C15 0.1(4) . . . . ?
C12 N13 C14 C15 -176.8(3) . . . . ?
N13 C14 C15 N16 0.0(4) . . . . ?
C14 C15 N16 C17 -0.1(4) . . . . ?
C14 C15 N16 C18 178.3(3) . . . . ?
C14 N13 C17 N16 -0.2(3) . . . . ?
C12 N13 C17 N16 176.8(3) . . . . ?
C14 N13 C17 Se1 -178.6(2) . . . . ?
C12 N13 C17 Se1 -1.6(5) . . . . ?
C15 N16 C17 N13 0.1(3) . . . . ?
C18 N16 C17 N13 -178.2(3) . . . . ?
C15 N16 C17 Se1 178.6(2) . . . . ?
C18 N16 C17 Se1 0.2(4) . . . . ?
C17 N16 C18 C19 -69.2(4) . . . . ?
C15 N16 C18 C19 112.7(3) . . . . ?
C17 N16 C18 C31 114.5(3) . . . . ?
C15 N16 C18 C31 -63.7(4) . . . . ?
C31 C18 C19 C20 1.6(5) . . . . ?
N16 C18 C19 C20 -174.8(3) . . . . ?
C18 C19 C20 C21 3.1(5) . . . . ?
C19 C20 C21 N22 175.3(3) . . . . ?
C19 C20 C21 C30 -2.9(4) . . . . ?
C20 C21 N22 C23 167.8(3) . . . . ?
C30 C21 N22 C23 -14.0(4) . . . . ?
C20 C21 N22 C39 -2.0(4) . . . . ?
C30 C21 N22 C39 176.2(3) . . . . ?
C21 N22 C23 C24 -171.5(3) . . . . ?
C39 N22 C23 C24 -1.6(4) . . . . ?
C21 N22 C23 C28 9.3(4) . . . . ?
C39 N22 C23 C28 179.2(3) . . . . ?
N22 C23 C24 C25 175.5(3) . . . . ?
C28 C23 C24 C25 -5.2(5) . . . . ?
C23 C24 C25 C26 -3.9(5) . . . . ?
C24 C25 C26 C27 5.3(6) . . . . ?
C25 C26 C27 O45 -173.1(3) . . . . ?
C25 C26 C27 C28 2.4(5) . . . . ?
N22 C23 C28 C29 8.7(4) . . . . ?
C24 C23 C28 C29 -170.6(3) . . . . ?
N22 C23 C28 C27 -168.4(3) . . . . ?
C24 C23 C28 C27 12.3(5) . . . . ?
O45 C27 C28 C23 164.9(3) . . . . ?
C26 C27 C28 C23 -11.0(5) . . . . ?
O45 C27 C28 C29 -12.0(5) . . . . ?
C26 C27 C28 C29 172.1(3) . . . . ?
C23 C28 C29 C30 -21.1(4) . . . . ?
C27 C28 C29 C30 155.8(3) . . . . ?
C23 C28 C29 C38 156.6(3) . . . . ?
C27 C28 C29 C38 -26.5(5) . . . . ?
C28 C29 C30 C21 16.5(4) . . . . ?
C38 C29 C30 C21 -161.4(3) . . . . ?
C28 C29 C30 C31 -162.7(3) . . . . ?
C38 C29 C30 C31 19.4(4) . . . . ?
N22 C21 C30 C29 0.7(4) . . . . ?
C20 C21 C30 C29 178.9(3) . . . . ?
N22 C21 C30 C31 179.9(3) . . . . ?
C20 C21 C30 C31 -1.9(4) . . . . ?
C19 C18 C31 N32 172.2(3) . . . . ?
N16 C18 C31 N32 -11.5(5) . . . . ?
C19 C18 C31 C30 -6.4(4) . . . . ?
N16 C18 C31 C30 169.9(3) . . . . ?
C29 C30 C31 C18 -174.3(3) . . . . ?
C21 C30 C31 C18 6.5(4) . . . . ?
C29 C30 C31 N32 7.0(4) . . . . ?
C21 C30 C31 N32 -172.2(3) . . . . ?
C18 C31 N32 C33 154.2(3) . . . . ?
C30 C31 N32 C33 -27.2(4) . . . . ?
C18 C31 N32 C42 -34.5(4) . . . . ?
C30 C31 N32 C42 144.1(3) . . . . ?
C31 N32 C33 C38 20.1(4) . . . . ?
C42 N32 C33 C38 -151.3(3) . . . . ?
C31 N32 C33 C34 -159.5(3) . . . . ?
C42 N32 C33 C34 29.0(4) . . . . ?
N32 C33 C34 C35 174.0(3) . . . . ?
C38 C33 C34 C35 -5.7(5) . . . . ?
C33 C34 C35 C36 -1.8(5) . . . . ?
C34 C35 C36 C37 3.3(5) . . . . ?
C35 C36 C37 O47 -174.5(3) . . . . ?
C35 C36 C37 C38 2.7(5) . . . . ?
N32 C33 C38 C37 -168.5(3) . . . . ?
C34 C33 C38 C37 11.2(5) . . . . ?
N32 C33 C38 C29 7.2(4) . . . . ?
C34 C33 C38 C29 -173.2(3) . . . . ?
O47 C37 C38 C33 167.7(3) . . . . ?
C36 C37 C38 C33 -9.7(5) . . . . ?
O47 C37 C38 C29 -7.6(5) . . . . ?
C36 C37 C38 C29 175.0(3) . . . . ?
C30 C29 C38 C33 -26.5(4) . . . . ?
C28 C29 C38 C33 155.8(3) . . . . ?
C30 C29 C38 C37 148.8(3) . . . . ?
C28 C29 C38 C37 -28.9(5) . . . . ?
C21 N22 C39 C40 89.7(3) . . . . ?
C23 N22 C39 C40 -80.4(3) . . . . ?
N22 C39 C40 C41 170.9(3) . . . . ?
C33 N32 C42 C43 58.7(4) . . . . ?
C31 N32 C42 C43 -112.6(3) . . . . ?
N32 C42 C43 C44 63.7(4) . . . . ?
C26 C27 O45 C46 -2.3(5) . . . . ?
C28 C27 O45 C46 -178.1(3) . . . . ?
C36 C37 O47 C48 0.4(5) . . . . ?
C38 C37 O47 C48 -176.9(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352607
