#------------------------------------------------------------------------------
#$Date: 2024-04-05 07:52:46 +0200 (Fri 05 de Apr de 2024) $
#$Revision: 291084 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/13/1571386.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_1571386
loop_
_publ_author_name
'Stumbo, Emily E.'
'Hodge, Emarald K.'
'Williams, Matthew'
'Thornton, Diana A.'
'McMillen, Colin D.'
'Pienkos, Jared A.'
_publ_section_title
;
 Synthesis and Crystallographic Characterization of Heteroleptic Ir(III)
 Complexes Containing the N-oxide Functional Group and Crystallographic
 Characterization of Ir(III) N-oxide Precursors
;
_journal_issue                   3
_journal_name_full               Crystals
_journal_page_first              281
_journal_paper_doi               10.3390/cryst14030281
_journal_volume                  14
_journal_year                    2024
_chemical_formula_sum            'C28.5 H19 Cl F4 Ir N4 O2.5'
_chemical_formula_weight         761.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 107.127(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.1167(11)
_cell_length_b                   16.8038(10)
_cell_length_c                   17.1342(9)
_cell_measurement_reflns_used    9453
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.44
_cell_volume                     5535.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            137437
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.080
_diffrn_reflns_theta_min         2.217
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    4.984
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_description       block
_exptl_crystal_F_000             2944
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.116
_refine_diff_density_max         2.151
_refine_diff_density_min         -2.036
_refine_diff_density_rms         0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     794
_refine_ls_number_reflns         16232
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0184P)²+35.0483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13509
_reflns_number_total             16232
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Ir-NO-NN-combined-CIF.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C28.50 H19 Cl F4 Ir N4 O2.50'
_cod_database_code               1571386
_shelx_shelxl_version_number     2016/6
_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   0.392
_shelx_estimated_absorpt_t_max   0.596
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'
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
Ir1 Ir 0.53719(2) 0.77868(2) 0.87782(2) 0.01601(4) Uani 1 1 d . . . . .
Ir2 Ir -0.06724(2) 0.76996(2) 0.43020(2) 0.01719(4) Uani 1 1 d . . . . .
F1 F 0.3366(2) 0.9859(2) 0.7244(2) 0.0551(10) Uani 1 1 d . . . . .
F2 F 0.46754(18) 0.86805(19) 0.57076(17) 0.0374(7) Uani 1 1 d . . . . .
F3 F 0.77418(14) 0.94352(17) 0.90811(18) 0.0306(6) Uani 1 1 d . . . . .
F4 F 0.64657(17) 1.00709(18) 1.08739(18) 0.0373(7) Uani 1 1 d . . . . .
F5 F 0.0403(2) 0.7754(2) 0.1767(2) 0.0506(9) Uani 1 1 d . . . . .
F6 F 0.1390(2) 0.9450(2) 0.3961(3) 0.0584(11) Uani 1 1 d . . . . .
F7 F 0.16556(16) 0.6134(2) 0.5950(2) 0.0431(8) Uani 1 1 d . . . . .
F8 F 0.00863(15) 0.47862(16) 0.38024(19) 0.0316(6) Uani 1 1 d . . . . .
O1 O 0.59081(15) 0.68933(18) 0.96305(17) 0.0192(6) Uani 1 1 d . . . . .
O2 O 0.58292(17) 0.5626(2) 0.9987(2) 0.0276(7) Uani 1 1 d . . . . .
O3 O -0.14888(16) 0.85755(18) 0.3955(2) 0.0231(6) Uani 1 1 d . . . . .
O4 O -0.24210(18) 0.9038(2) 0.4272(2) 0.0339(8) Uani 1 1 d . . . . .
N1 N 0.46784(18) 0.6813(2) 0.8475(2) 0.0181(7) Uani 1 1 d . . . . .
N2 N 0.3916(2) 0.5399(3) 0.8176(3) 0.0319(9) Uani 1 1 d . . . . .
N3 N 0.57735(19) 0.7445(2) 0.7880(2) 0.0198(7) Uani 1 1 d . . . . .
N4 N 0.50165(18) 0.8271(2) 0.9680(2) 0.0192(7) Uani 1 1 d . . . . .
N5 N -0.13125(19) 0.7400(2) 0.5053(2) 0.0199(7) Uani 1 1 d . . . . .
N6 N -0.2268(2) 0.7122(2) 0.5907(2) 0.0242(8) Uani 1 1 d . . . . .
N7 N -0.00880(19) 0.8528(2) 0.5082(2) 0.0216(7) Uani 1 1 d . . . . .
N8 N -0.11889(17) 0.6869(2) 0.3471(2) 0.0179(7) Uani 1 1 d . . . . .
C1 C 0.5605(2) 0.6216(3) 0.9570(3) 0.0198(8) Uani 1 1 d . . . . .
C2 C 0.4911(2) 0.6150(3) 0.8918(3) 0.0202(8) Uani 1 1 d . . . . .
C3 C 0.4523(2) 0.5459(3) 0.8765(3) 0.0262(9) Uani 1 1 d . . . . .
H3 H 0.469452 0.500512 0.909266 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3693(3) 0.6054(3) 0.7742(3) 0.0308(10) Uani 1 1 d . . . . .
C5 C 0.4071(2) 0.6768(3) 0.7888(3) 0.0252(9) Uani 1 1 d . . . . .
H5 H 0.389392 0.722367 0.756641 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3019(3) 0.6008(4) 0.7082(4) 0.0479(16) Uani 1 1 d . . . . .
H6A H 0.309106 0.574354 0.660324 0.072 Uiso 1 1 calc R U . . .
H6B H 0.284029 0.654699 0.693164 0.072 Uiso 1 1 calc R U . . .
H6C H 0.268278 0.570445 0.727512 0.072 Uiso 1 1 calc R U . . .
C7 C 0.4821(2) 0.8491(2) 0.7887(3) 0.0212(8) Uani 1 1 d . . . . .
C8 C 0.4271(3) 0.8989(3) 0.7910(3) 0.0284(10) Uani 1 1 d . . . . .
H8 H 0.415470 0.906038 0.840373 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3898(3) 0.9379(3) 0.7203(3) 0.0371(12) Uani 1 1 d . . . . .
C10 C 0.4020(3) 0.9293(3) 0.6458(3) 0.0377(12) Uani 1 1 d . . . . .
H10 H 0.374942 0.956221 0.598273 0.045 Uiso 1 1 calc R U . . .
C11 C 0.4563(3) 0.8791(3) 0.6443(3) 0.0288(10) Uani 1 1 d . . . . .
C12 C 0.4973(2) 0.8393(3) 0.7126(3) 0.0219(8) Uani 1 1 d . . . . .
C13 C 0.5545(2) 0.7842(3) 0.7150(3) 0.0216(8) Uani 1 1 d . . . . .
C14 C 0.5862(3) 0.7713(3) 0.6537(3) 0.0276(10) Uani 1 1 d . . . . .
H14 H 0.571381 0.800239 0.603976 0.033 Uiso 1 1 calc R U . . .
C15 C 0.6389(3) 0.7165(3) 0.6659(3) 0.0311(11) Uani 1 1 d . . . . .
H15 H 0.660603 0.707489 0.624339 0.037 Uiso 1 1 calc R U . . .
C16 C 0.6606(2) 0.6744(3) 0.7382(3) 0.0272(10) Uani 1 1 d . . . . .
H16 H 0.696293 0.635599 0.746481 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6291(2) 0.6900(3) 0.7985(3) 0.0209(8) Uani 1 1 d . . . . .
H17 H 0.644185 0.661802 0.848664 0.025 Uiso 1 1 calc R U . . .
C18 C 0.6096(2) 0.8626(2) 0.9193(2) 0.0174(7) Uani 1 1 d . . . . .
C19 C 0.6683(2) 0.8769(3) 0.8927(3) 0.0233(8) Uani 1 1 d . . . . .
H19 H 0.674493 0.848494 0.847432 0.028 Uiso 1 1 calc R U . . .
C20 C 0.7166(2) 0.9324(3) 0.9328(3) 0.0228(8) Uani 1 1 d . . . . .
C21 C 0.7102(3) 0.9780(3) 0.9974(3) 0.0259(9) Uani 1 1 d . . . . .
H21 H 0.743588 1.017106 1.022849 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6522(3) 0.9631(3) 1.0227(3) 0.0265(9) Uani 1 1 d . . . . .
C23 C 0.6016(2) 0.9074(2) 0.9866(3) 0.0200(8) Uani 1 1 d . . . . .
C24 C 0.5401(2) 0.8877(3) 1.0119(3) 0.0215(8) Uani 1 1 d . . . . .
C25 C 0.5193(3) 0.9236(3) 1.0745(3) 0.0277(10) Uani 1 1 d . . . . .
H25 H 0.546122 0.965685 1.105383 0.033 Uiso 1 1 calc R U . . .
C26 C 0.4598(3) 0.8982(3) 1.0916(3) 0.0337(11) Uani 1 1 d . . . . .
H26 H 0.445423 0.922892 1.133767 0.040 Uiso 1 1 calc R U . . .
C27 C 0.4214(3) 0.8368(3) 1.0471(3) 0.0313(10) Uani 1 1 d . . . . .
H27 H 0.380543 0.818391 1.058375 0.038 Uiso 1 1 calc R U . . .
C28 C 0.4437(2) 0.8022(3) 0.9854(3) 0.0264(9) Uani 1 1 d . . . . .
H28 H 0.417381 0.759791 0.954587 0.032 Uiso 1 1 calc R U . . .
C29 C -0.1943(2) 0.8555(3) 0.4344(3) 0.0228(8) Uani 1 1 d . . . . .
C30 C -0.1880(2) 0.7867(3) 0.4932(3) 0.0208(8) Uani 1 1 d . . . . .
C31 C -0.2364(2) 0.7709(3) 0.5359(3) 0.0244(9) Uani 1 1 d . . . . .
H31 H -0.277029 0.802775 0.525602 0.029 Uiso 1 1 calc R U . . .
C32 C -0.1689(2) 0.6679(3) 0.6042(3) 0.0216(8) Uani 1 1 d . . . . .
C33 C -0.1215(2) 0.6813(2) 0.5601(3) 0.0199(8) Uani 1 1 d . . . . .
H33 H -0.081737 0.648094 0.569249 0.024 Uiso 1 1 calc R U . . .
C34 C -0.1565(3) 0.6044(3) 0.6688(3) 0.0268(9) Uani 1 1 d . . . . .
H34A H -0.144434 0.629304 0.722892 0.040 Uiso 1 1 calc R U . . .
H34B H -0.118258 0.569947 0.665068 0.040 Uiso 1 1 calc R U . . .
H34C H -0.198824 0.572474 0.660578 0.040 Uiso 1 1 calc R U . . .
C35 C -0.0075(2) 0.8072(3) 0.3626(3) 0.0222(8) Uani 1 1 d . . . . .
C36 C -0.0082(3) 0.7786(3) 0.2858(3) 0.0260(9) Uani 1 1 d . . . . .
H36 H -0.042276 0.740942 0.258040 0.031 Uiso 1 1 calc R U . . .
C37 C 0.0409(3) 0.8055(3) 0.2508(3) 0.0364(12) Uani 1 1 d . . . . .
C38 C 0.0912(3) 0.8608(3) 0.2867(4) 0.0390(13) Uani 1 1 d . . . . .
H38 H 0.124650 0.877981 0.261056 0.047 Uiso 1 1 calc R U . . .
C39 C 0.0904(3) 0.8896(3) 0.3609(4) 0.0371(12) Uani 1 1 d . . . . .
C40 C 0.0431(2) 0.8643(3) 0.4015(3) 0.0281(10) Uani 1 1 d . . . . .
C41 C 0.0414(2) 0.8906(3) 0.4821(3) 0.0274(10) Uani 1 1 d . . . . .
C42 C 0.0835(3) 0.9489(3) 0.5322(4) 0.0374(12) Uani 1 1 d . . . . .
H42 H 0.118848 0.974692 0.515140 0.045 Uiso 1 1 calc R U . . .
C43 C 0.0734(3) 0.9687(3) 0.6062(4) 0.0432(14) Uani 1 1 d . . . . .
H43 H 0.101631 1.008143 0.639918 0.052 Uiso 1 1 calc R U . . .
C44 C 0.0224(3) 0.9310(3) 0.6309(4) 0.0376(12) Uani 1 1 d . . . . .
H44 H 0.014826 0.944172 0.681522 0.045 Uiso 1 1 calc R U . . .
C45 C -0.0176(3) 0.8736(3) 0.5809(3) 0.0294(10) Uani 1 1 d . . . . .
H45 H -0.052760 0.847649 0.598134 0.035 Uiso 1 1 calc R U . . .
C46 C 0.0008(2) 0.6805(2) 0.4598(2) 0.0180(7) Uani 1 1 d . . . . .
C47 C 0.0645(2) 0.6806(3) 0.5207(3) 0.0220(8) Uani 1 1 d . . . . .
H47 H 0.079843 0.726782 0.552929 0.026 Uiso 1 1 calc R U . . .
C48 C 0.1050(2) 0.6130(3) 0.5335(3) 0.0262(9) Uani 1 1 d . . . . .
C49 C 0.0879(2) 0.5448(3) 0.4879(3) 0.0280(10) Uani 1 1 d . . . . .
H49 H 0.117230 0.499337 0.498225 0.034 Uiso 1 1 calc R U . . .
C50 C 0.0256(2) 0.5458(3) 0.4260(3) 0.0231(8) Uani 1 1 d . . . . .
C51 C -0.0189(2) 0.6112(2) 0.4108(3) 0.0181(7) Uani 1 1 d . . . . .
C52 C -0.0864(2) 0.6161(3) 0.3473(3) 0.0199(8) Uani 1 1 d . . . . .
C53 C -0.1169(2) 0.5578(3) 0.2896(3) 0.0242(9) Uani 1 1 d . . . . .
H53 H -0.093850 0.508459 0.289359 0.029 Uiso 1 1 calc R U . . .
C54 C -0.1805(3) 0.5721(3) 0.2330(3) 0.0281(9) Uani 1 1 d . . . . .
H54 H -0.201356 0.532933 0.193350 0.034 Uiso 1 1 calc R U . . .
C55 C -0.2138(2) 0.6443(3) 0.2344(3) 0.0253(9) Uani 1 1 d . . . . .
H55 H -0.257867 0.655020 0.196377 0.030 Uiso 1 1 calc R U . . .
C56 C -0.1815(2) 0.7002(3) 0.2920(3) 0.0221(8) Uani 1 1 d . . . . .
H56 H -0.204070 0.749645 0.293065 0.027 Uiso 1 1 calc R U . . .
C57 C 0.2126(6) 0.8750(6) 0.7810(7) 0.1005(17) Uani 0.3333 1 d D U P A 1
H57A H 0.197141 0.927380 0.755727 0.121 Uiso 0.3333 1 calc R U P A 1
H57B H 0.262021 0.881293 0.813186 0.121 Uiso 0.3333 1 calc R U P A 1
Cl2 Cl 0.2117(4) 0.8130(5) 0.7044(5) 0.0916(17) Uani 0.3333 1 d D U P A 1
Cl1 Cl 0.1679(5) 0.8587(7) 0.8492(7) 0.102(2) Uani 0.3333 1 d D U P A 1
Cl3 Cl 0.2801(4) 0.6967(7) 0.8873(7) 0.130(3) Uani 0.3333 1 d D U P B 2
Cl4 Cl 0.2393(5) 0.7235(7) 1.0327(7) 0.133(3) Uani 0.3333 1 d D U P B 2
C58 C 0.2818(14) 0.6668(13) 0.9814(11) 0.131(4) Uani 0.3333 1 d D U P B 2
H58A H 0.331025 0.663146 1.014885 0.158 Uiso 0.3333 1 calc R U P B 2
H58B H 0.262066 0.612455 0.977069 0.158 Uiso 0.3333 1 calc R U P B 2
C59 C 0.2126(6) 0.8750(6) 0.7810(7) 0.1005(17) Uani 0.3333 1 d D U P C 3
H59A H 0.191682 0.876639 0.720962 0.121 Uiso 0.3333 1 calc R U P C 3
H59B H 0.243775 0.921639 0.796575 0.121 Uiso 0.3333 1 calc R U P C 3
Cl5 Cl 0.1474(4) 0.8840(5) 0.8259(6) 0.0860(18) Uani 0.3333 1 d D U P C 3
Cl6 Cl 0.2617(5) 0.7908(6) 0.8053(7) 0.116(2) Uani 0.3333 1 d D U P C 3
O4W O -0.2802(2) 0.5146(3) 0.0558(3) 0.0494(11) Uani 1 1 d D . . . .
H4A H -0.264(3) 0.532(4) 0.019(3) 0.05(2) Uiso 1 1 d D . . . .
H4B H -0.320(2) 0.535(4) 0.051(4) 0.06(2) Uiso 1 1 d 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 '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'
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
C7 Ir1 C18 92.03(17) . . ?
C7 Ir1 N3 80.91(17) . . ?
C18 Ir1 N3 93.36(16) . . ?
C7 Ir1 N4 95.90(16) . . ?
C18 Ir1 N4 80.30(16) . . ?
N3 Ir1 N4 172.85(15) . . ?
C7 Ir1 N1 95.40(16) . . ?
C18 Ir1 N1 172.54(14) . . ?
N3 Ir1 N1 88.59(14) . . ?
N4 Ir1 N1 98.12(14) . . ?
C7 Ir1 O1 172.18(14) . . ?
C18 Ir1 O1 94.83(14) . . ?
N3 Ir1 O1 94.90(13) . . ?
N4 Ir1 O1 88.98(12) . . ?
N1 Ir1 O1 77.82(12) . . ?
C46 Ir2 C35 84.17(16) . . ?
C46 Ir2 N8 80.37(15) . . ?
C35 Ir2 N8 94.52(16) . . ?
C46 Ir2 N7 97.33(16) . . ?
C35 Ir2 N7 80.69(17) . . ?
N8 Ir2 N7 174.90(14) . . ?
C46 Ir2 N5 99.21(15) . . ?
C35 Ir2 N5 175.37(16) . . ?
N8 Ir2 N5 89.19(14) . . ?
N7 Ir2 N5 95.69(15) . . ?
C46 Ir2 O3 174.21(14) . . ?
C35 Ir2 O3 99.52(15) . . ?
N8 Ir2 O3 94.83(13) . . ?
N7 Ir2 O3 87.71(13) . . ?
N5 Ir2 O3 77.36(13) . . ?
C1 O1 Ir1 115.7(3) . . ?
C29 O3 Ir2 116.1(3) . . ?
C5 N1 C2 117.7(4) . . ?
C5 N1 Ir1 128.3(3) . . ?
C2 N1 Ir1 113.9(3) . . ?
C4 N2 C3 116.3(4) . . ?
C17 N3 C13 119.1(4) . . ?
C17 N3 Ir1 123.6(3) . . ?
C13 N3 Ir1 117.0(3) . . ?
C28 N4 C24 119.7(4) . . ?
C28 N4 Ir1 123.9(3) . . ?
C24 N4 Ir1 116.4(3) . . ?
C33 N5 C30 118.6(4) . . ?
C33 N5 Ir2 127.5(3) . . ?
C30 N5 Ir2 113.9(3) . . ?
C31 N6 C32 118.0(4) . . ?
C45 N7 C41 119.2(4) . . ?
C45 N7 Ir2 124.8(3) . . ?
C41 N7 Ir2 115.9(3) . . ?
C56 N8 C52 119.7(4) . . ?
C56 N8 Ir2 123.5(3) . . ?
C52 N8 Ir2 116.8(3) . . ?
O2 C1 O1 125.9(4) . . ?
O2 C1 C2 118.2(4) . . ?
O1 C1 C2 115.9(4) . . ?
N1 C2 C3 120.2(4) . . ?
N1 C2 C1 116.6(4) . . ?
C3 C2 C1 123.3(4) . . ?
N2 C3 C2 123.1(4) . . ?
N2 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
N2 C4 C5 122.1(4) . . ?
N2 C4 C6 117.7(5) . . ?
C5 C4 C6 120.2(5) . . ?
N1 C5 C4 120.7(4) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 118.5(4) . . ?
C8 C7 Ir1 127.0(3) . . ?
C12 C7 Ir1 114.2(3) . . ?
C9 C8 C7 119.2(5) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
F1 C9 C10 118.0(5) . . ?
F1 C9 C8 117.9(5) . . ?
C10 C9 C8 124.1(5) . . ?
C9 C10 C11 116.0(5) . . ?
C9 C10 H10 122.0 . . ?
C11 C10 H10 122.0 . . ?
F2 C11 C10 116.6(4) . . ?
F2 C11 C12 119.8(5) . . ?
C10 C11 C12 123.6(5) . . ?
C11 C12 C7 118.5(4) . . ?
C11 C12 C13 126.4(4) . . ?
C7 C12 C13 115.0(4) . . ?
N3 C13 C14 120.3(4) . . ?
N3 C13 C12 112.4(4) . . ?
C14 C13 C12 127.2(4) . . ?
C15 C14 C13 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 118.6(5) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N3 C17 C16 122.0(4) . . ?
N3 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C19 C18 C23 118.5(4) . . ?
C19 C18 Ir1 126.7(3) . . ?
C23 C18 Ir1 114.6(3) . . ?
C20 C19 C18 119.4(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
F3 C20 C19 118.7(4) . . ?
F3 C20 C21 117.6(4) . . ?
C19 C20 C21 123.8(4) . . ?
C22 C21 C20 116.0(4) . . ?
C22 C21 H21 122.0 . . ?
C20 C21 H21 122.0 . . ?
F4 C22 C21 115.9(4) . . ?
F4 C22 C23 120.1(4) . . ?
C21 C22 C23 124.0(4) . . ?
C22 C23 C18 118.3(4) . . ?
C22 C23 C24 126.5(4) . . ?
C18 C23 C24 115.2(4) . . ?
N4 C24 C25 119.7(4) . . ?
N4 C24 C23 113.4(4) . . ?
C25 C24 C23 126.8(4) . . ?
C26 C25 C24 120.2(5) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C27 C26 C25 119.7(4) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C28 118.7(5) . . ?
C26 C27 H27 120.7 . . ?
C28 C27 H27 120.7 . . ?
N4 C28 C27 122.0(5) . . ?
N4 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
O4 C29 O3 125.6(4) . . ?
O4 C29 C30 118.6(4) . . ?
O3 C29 C30 115.8(4) . . ?
N5 C30 C31 119.6(4) . . ?
N5 C30 C29 116.5(4) . . ?
C31 C30 C29 123.8(4) . . ?
N6 C31 C30 121.8(4) . . ?
N6 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
N6 C32 C33 120.8(4) . . ?
N6 C32 C34 117.8(4) . . ?
C33 C32 C34 121.3(4) . . ?
N5 C33 C32 121.1(4) . . ?
N5 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C40 118.9(4) . . ?
C36 C35 Ir2 126.7(3) . . ?
C40 C35 Ir2 114.2(3) . . ?
C37 C36 C35 119.2(5) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
F5 C37 C36 118.3(5) . . ?
F5 C37 C38 118.0(5) . . ?
C36 C37 C38 123.8(5) . . ?
C39 C38 C37 116.4(5) . . ?
C39 C38 H38 121.8 . . ?
C37 C38 H38 121.8 . . ?
F6 C39 C38 116.9(5) . . ?
F6 C39 C40 119.6(5) . . ?
C38 C39 C40 123.5(5) . . ?
C39 C40 C35 118.1(5) . . ?
C39 C40 C41 125.9(5) . . ?
C35 C40 C41 116.0(4) . . ?
N7 C41 C42 119.3(5) . . ?
N7 C41 C40 113.1(4) . . ?
C42 C41 C40 127.6(5) . . ?
C43 C42 C41 120.2(5) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C44 C43 C42 119.7(5) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C45 118.8(5) . . ?
C43 C44 H44 120.6 . . ?
C45 C44 H44 120.6 . . ?
N7 C45 C44 122.8(5) . . ?
N7 C45 H45 118.6 . . ?
C44 C45 H45 118.6 . . ?
C47 C46 C51 118.5(4) . . ?
C47 C46 Ir2 126.9(3) . . ?
C51 C46 Ir2 114.6(3) . . ?
C48 C47 C46 119.3(4) . . ?
C48 C47 H47 120.4 . . ?
C46 C47 H47 120.4 . . ?
F7 C48 C49 117.7(4) . . ?
F7 C48 C47 118.3(4) . . ?
C49 C48 C47 124.0(4) . . ?
C48 C49 C50 116.5(4) . . ?
C48 C49 H49 121.8 . . ?
C50 C49 H49 121.8 . . ?
F8 C50 C49 116.7(4) . . ?
F8 C50 C51 120.5(4) . . ?
C49 C50 C51 122.7(4) . . ?
C50 C51 C46 118.9(4) . . ?
C50 C51 C52 125.9(4) . . ?
C46 C51 C52 115.2(4) . . ?
N8 C52 C53 120.1(4) . . ?
N8 C52 C51 113.0(4) . . ?
C53 C52 C51 126.9(4) . . ?
C54 C53 C52 119.8(4) . . ?
C54 C53 H53 120.1 . . ?
C52 C53 H53 120.1 . . ?
C53 C54 C55 119.5(4) . . ?
C53 C54 H54 120.3 . . ?
C55 C54 H54 120.3 . . ?
C56 C55 C54 118.6(4) . . ?
C56 C55 H55 120.7 . . ?
C54 C55 H55 120.7 . . ?
N8 C56 C55 122.3(4) . . ?
N8 C56 H56 118.9 . . ?
C55 C56 H56 118.9 . . ?
Cl2 C57 Cl1 123.7(9) . . ?
Cl2 C57 H57A 106.4 . . ?
Cl1 C57 H57A 106.4 . . ?
Cl2 C57 H57B 106.4 . . ?
Cl1 C57 H57B 106.4 . . ?
H57A C57 H57B 106.5 . . ?
Cl3 C58 Cl4 117.4(11) . . ?
Cl3 C58 H58A 107.9 . . ?
Cl4 C58 H58A 107.9 . . ?
Cl3 C58 H58B 107.9 . . ?
Cl4 C58 H58B 107.9 . . ?
H58A C58 H58B 107.2 . . ?
Cl6 C59 Cl5 115.4(8) . . ?
Cl6 C59 H59A 108.4 . . ?
Cl5 C59 H59A 108.4 . . ?
Cl6 C59 H59B 108.4 . . ?
Cl5 C59 H59B 108.4 . . ?
H59A C59 H59B 107.5 . . ?
H4A O4W H4B 111(4) . . ?
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
Ir1 C7 1.991(4) . ?
Ir1 C18 2.002(4) . ?
Ir1 N3 2.021(3) . ?
Ir1 N4 2.052(3) . ?
Ir1 N1 2.114(4) . ?
Ir1 O1 2.150(3) . ?
Ir2 C46 1.996(4) . ?
Ir2 C35 1.999(4) . ?
Ir2 N8 2.045(3) . ?
Ir2 N7 2.045(4) . ?
Ir2 N5 2.131(4) . ?
Ir2 O3 2.155(3) . ?
F1 C9 1.359(6) . ?
F2 C11 1.356(5) . ?
F3 C20 1.358(5) . ?
F4 C22 1.365(5) . ?
F5 C37 1.363(6) . ?
F6 C39 1.357(6) . ?
F7 C48 1.355(5) . ?
F8 C50 1.360(5) . ?
O1 C1 1.282(5) . ?
O2 C1 1.227(5) . ?
O3 C29 1.281(5) . ?
O4 C29 1.236(5) . ?
N1 C5 1.336(6) . ?
N1 C2 1.351(5) . ?
N2 C4 1.330(7) . ?
N2 C3 1.339(6) . ?
N3 C17 1.357(6) . ?
N3 C13 1.373(6) . ?
N4 C28 1.353(6) . ?
N4 C24 1.363(6) . ?
N5 C33 1.336(5) . ?
N5 C30 1.350(5) . ?
N6 C31 1.335(6) . ?
N6 C32 1.343(6) . ?
N7 C45 1.353(6) . ?
N7 C41 1.375(6) . ?
N8 C56 1.352(5) . ?
N8 C52 1.357(5) . ?
C1 C2 1.513(6) . ?
C2 C3 1.381(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(7) . ?
C4 C6 1.490(7) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.397(6) . ?
C7 C12 1.434(6) . ?
C8 C9 1.387(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(8) . ?
C10 C11 1.386(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(6) . ?
C12 C13 1.467(6) . ?
C13 C14 1.396(6) . ?
C14 C15 1.374(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.405(6) . ?
C18 C23 1.425(6) . ?
C19 C20 1.376(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(6) . ?
C21 C22 1.381(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(6) . ?
C23 C24 1.464(6) . ?
C24 C25 1.399(6) . ?
C25 C26 1.381(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.514(6) . ?
C30 C31 1.404(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.398(6) . ?
C32 C34 1.506(6) . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.397(7) . ?
C35 C40 1.416(7) . ?
C36 C37 1.374(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.378(8) . ?
C38 C39 1.366(9) . ?
C38 H38 0.9500 . ?
C39 C40 1.400(7) . ?
C40 C41 1.459(7) . ?
C41 C42 1.409(7) . ?
C42 C43 1.382(9) . ?
C42 H42 0.9500 . ?
C43 C44 1.373(8) . ?
C43 H43 0.9500 . ?
C44 C45 1.380(7) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C47 1.394(6) . ?
C46 C51 1.423(6) . ?
C47 C48 1.377(6) . ?
C47 H47 0.9500 . ?
C48 C49 1.373(7) . ?
C49 C50 1.381(6) . ?
C49 H49 0.9500 . ?
C50 C51 1.392(6) . ?
C51 C52 1.471(6) . ?
C52 C53 1.399(6) . ?
C53 C54 1.381(6) . ?
C53 H53 0.9500 . ?
C54 C55 1.390(7) . ?
C54 H54 0.9500 . ?
C55 C56 1.378(6) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C57 Cl2 1.670(8) . ?
C57 Cl1 1.695(8) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
Cl3 C58 1.680(9) . ?
Cl4 C58 1.687(9) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 Cl6 1.705(8) . ?
C59 Cl5 1.713(8) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
O4W H4A 0.844(19) . ?
O4W H4B 0.848(19) . ?
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
O4W H4A O4 0.844(19) 2.06(3) 2.884(6) 165(6) 4_575
O4W H4B O2 0.848(19) 1.96(4) 2.757(5) 157(7) 1_454
