# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_4
_database_code_depnum_ccdc_archive 'CCDC 2302905'
_audit_update_record             
;
2023-10-23 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2023-07-20
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_diffrn_source_power             0.07
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C31 H15 F6 Ir N6 O2 S2'
_chemical_formula_moiety         'C31 H15 F6 Ir N6 O2 S2'
_exptl_crystal_colour_primary    pink
_chemical_formula_weight         873.81
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C3(H3), C10(H10), C11(H11), C13(H13), C16(H16), C20(H20),
 C19(H19), C23(H23), C24(H24), C26(H26), C29(H29), C30(H30), C31(H31)
2.b Fitted hexagon refined as free rotating group:
 C7(C6,C5,C4,C3,C2), C18(C17,C16,C15,C20,C19)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0618(6)
_cell_length_b                   20.7300(13)
_cell_length_c                   26.6333(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5555.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9786
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.70
_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_F_000             3376
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    5.043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.313124
_exptl_absorpt_correction_T_max  0.74543
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1613 before and 0.0616 after correction.
 
For component 2:
 wR2(int) was 0.2038 before and 0.0980 after correction.
 
For component 3:
 wR2(int) was 0.1434 before and 0.0672 after correction.
 
For component 4:
 wR2(int) was 0.1205 before and 0.0686 after correction.
 The Ratio of minimum to maximum transmission is 0.42.

Final HKLF 4 output contains 141016 reflections, Rint = 0.1060
 (51389 with I > 3sig(I), Rint = 0.0680)
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.464
_shelx_estimated_absorpt_T_max   0.539
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            5905
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_theta_min         2.108
_diffrn_reflns_theta_max         26.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5905
_reflns_number_gt                4566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+84.2439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5905
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.507
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

loop_
_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 0.52429(3) 0.26977(2) 0.41578(2) 0.01699(9) Uani 1 1 d . . . . .
S1 S 0.1336(2) 0.02631(10) 0.43835(9) 0.0295(5) Uani 1 1 d . . . . .
S2 S 0.9606(2) 0.49506(10) 0.41089(11) 0.0373(6) Uani 1 1 d . . . . .
F1 F 0.2094(6) 0.3976(3) 0.21960(19) 0.0413(14) Uani 1 1 d . . . . .
F2 F 0.4164(6) 0.4117(3) 0.2332(2) 0.0507(16) Uani 1 1 d . . . . .
F3 F 0.2723(7) 0.4516(3) 0.2836(2) 0.0506(16) Uani 1 1 d . . . . .
F4 F 0.6257(5) 0.0760(3) 0.2708(2) 0.0387(13) Uani 1 1 d . . . . .
F5 F 0.8284(6) 0.0837(3) 0.2478(2) 0.0456(15) Uani 1 1 d . . . . .
F6 F 0.7787(7) 0.0404(2) 0.3179(2) 0.0500(16) Uani 1 1 d . . . . .
O1 O 0.6296(5) 0.2522(2) 0.48495(18) 0.0183(12) Uani 1 1 d . . . . .
O2 O 0.6031(6) 0.2550(3) 0.5680(2) 0.0315(14) Uani 1 1 d . . . . .
N1 N 0.4079(6) 0.1896(3) 0.4217(2) 0.0191(14) Uani 1 1 d . . . . .
N2 N 0.3335(7) 0.1016(3) 0.4713(3) 0.0258(16) Uani 1 1 d . . . . .
N3 N 0.6503(6) 0.3471(3) 0.4074(2) 0.0190(14) Uani 1 1 d . . . . .
N4 N 0.7090(7) 0.4556(3) 0.4261(3) 0.0248(16) Uani 1 1 d . . . . .
N5 N 0.4016(6) 0.3162(3) 0.4707(2) 0.0179(14) Uani 1 1 d . . . . .
N6 N 0.2311(7) 0.3869(3) 0.4973(3) 0.0249(16) Uani 1 1 d . . . . .
C1 C 0.3008(8) 0.3999(4) 0.2558(3) 0.028(2) Uani 1 1 d . . . . .
C7 C 0.3996(5) 0.3361(2) 0.32517(18) 0.0216(17) Uani 1 1 d G . . . .
H7 H 0.459979 0.370681 0.330536 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4048(4) 0.2818(2) 0.35567(16) 0.0164(16) Uani 1 1 d G . . . .
C5 C 0.3165(5) 0.23117(19) 0.34782(17) 0.0213(17) Uani 1 1 d G . . . .
C4 C 0.2231(5) 0.2349(2) 0.30948(19) 0.0264(18) Uani 1 1 d G . . . .
H4 H 0.162775 0.200369 0.304120 0.032 Uiso 1 1 calc R U . . .
C3 C 0.2180(5) 0.2893(2) 0.27899(17) 0.028(2) Uani 1 1 d G . . . .
H3 H 0.154134 0.291879 0.252783 0.034 Uiso 1 1 calc R U . . .
C2 C 0.3062(5) 0.3399(2) 0.28683(17) 0.0193(17) Uani 1 1 d G . . . .
C8 C 0.3181(8) 0.1787(4) 0.3845(3) 0.0215(18) Uani 1 1 d . . . . .
C9 C 0.2370(8) 0.1233(4) 0.3888(3) 0.0231(18) Uani 1 1 d . . . . .
C10 C 0.1384(9) 0.0940(4) 0.3573(3) 0.029(2) Uani 1 1 d . . . . .
H10 H 0.118396 0.108866 0.324393 0.035 Uiso 1 1 calc R U . . .
C11 C 0.0771(9) 0.0435(4) 0.3789(3) 0.031(2) Uani 1 1 d . . . . .
H11 H 0.008921 0.019469 0.362743 0.037 Uiso 1 1 calc R U . . .
C12 C 0.2489(8) 0.0892(4) 0.4342(3) 0.0202(17) Uani 1 1 d . . . . .
C13 C 0.4133(8) 0.1505(4) 0.4623(3) 0.0215(17) Uani 1 1 d . . . . .
H13 H 0.480686 0.158990 0.486429 0.026 Uiso 1 1 calc R U . . .
C14 C 0.7485(8) 0.0887(4) 0.2868(3) 0.0246(18) Uani 1 1 d . . . . .
C18 C 0.7730(5) 0.27013(19) 0.36230(18) 0.0207(16) Uani 1 1 d G . . . .
C17 C 0.6628(4) 0.2308(2) 0.36938(17) 0.0194(16) Uani 1 1 d G . . . .
C16 C 0.6540(4) 0.1720(2) 0.34444(18) 0.0189(17) Uani 1 1 d G . . . .
H16 H 0.578611 0.145141 0.349279 0.023 Uiso 1 1 calc R U . . .
C15 C 0.7555(5) 0.15264(19) 0.31241(18) 0.0191(17) Uani 1 1 d G . . . .
C20 C 0.8657(4) 0.1920(2) 0.30533(18) 0.0276(19) Uani 1 1 d G . . . .
H20 H 0.935118 0.178741 0.283445 0.033 Uiso 1 1 calc R U . . .
C19 C 0.8745(4) 0.2507(2) 0.33028(19) 0.0211(17) Uani 1 1 d G . . . .
H19 H 0.949889 0.277633 0.325438 0.025 Uiso 1 1 calc R U . . .
C21 C 0.7707(8) 0.3334(4) 0.3869(3) 0.0220(17) Uani 1 1 d . . . . .
C22 C 0.8707(8) 0.3804(4) 0.3897(3) 0.0197(17) Uani 1 1 d . . . . .
C23 C 1.0078(8) 0.3802(4) 0.3769(3) 0.0274(19) Uani 1 1 d . . . . .
H23 H 1.053694 0.343661 0.364115 0.033 Uiso 1 1 calc R U . . .
C24 C 1.0659(9) 0.4389(4) 0.3853(3) 0.033(2) Uani 1 1 d . . . . .
H24 H 1.156358 0.447727 0.377726 0.039 Uiso 1 1 calc R U . . .
C25 C 0.8309(8) 0.4406(4) 0.4094(3) 0.0242(18) Uani 1 1 d . . . . .
C26 C 0.6269(9) 0.4063(4) 0.4253(3) 0.0248(19) Uani 1 1 d . . . . .
H26 H 0.541047 0.413560 0.439038 0.030 Uiso 1 1 calc R U . . .
C27 C 0.5698(8) 0.2696(4) 0.5247(3) 0.0238(17) Uani 1 1 d . . . . .
C28 C 0.4477(8) 0.3109(4) 0.5181(3) 0.0207(17) Uani 1 1 d . . . . .
C29 C 0.3865(8) 0.3429(4) 0.5563(3) 0.0220(18) Uani 1 1 d . . . . .
H29 H 0.415646 0.338525 0.590019 0.026 Uiso 1 1 calc R U . . .
C30 C 0.2790(9) 0.3824(4) 0.5438(3) 0.030(2) Uani 1 1 d . . . . .
H30 H 0.238289 0.407157 0.569631 0.036 Uiso 1 1 calc R U . . .
C31 C 0.2945(8) 0.3521(4) 0.4628(3) 0.0218(18) Uani 1 1 d . . . . .
H31 H 0.259911 0.352997 0.429620 0.026 Uiso 1 1 calc R U . . .


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 O1 2.156(5) . ?
Ir1 N1 2.039(6) . ?
Ir1 N3 2.056(6) . ?
Ir1 N5 2.142(6) . ?
Ir1 C6 2.018(3) . ?
Ir1 C17 2.030(3) . ?
S1 C11 1.721(9) . ?
S1 C12 1.748(8) . ?
S2 C24 1.715(10) . ?
S2 C25 1.726(8) . ?
F1 C1 1.334(9) . ?
F2 C1 1.332(10) . ?
F3 C1 1.334(10) . ?
F4 C14 1.333(9) . ?
F5 C14 1.319(9) . ?
F6 C14 1.334(10) . ?
O1 C27 1.269(9) . ?
O2 C27 1.240(9) . ?
N1 C8 1.361(10) . ?
N1 C13 1.353(10) . ?
N2 C12 1.330(10) . ?
N2 C13 1.314(10) . ?
N3 C21 1.359(10) . ?
N3 C26 1.337(10) . ?
N4 C25 1.340(10) . ?
N4 C26 1.315(10) . ?
N5 C28 1.350(9) . ?
N5 C31 1.326(10) . ?
N6 C30 1.332(11) . ?
N6 C31 1.331(10) . ?
C1 C2 1.495(9) . ?
C7 H7 0.9500 . ?
C7 C6 1.3900 . ?
C7 C2 1.3900 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C5 C8 1.463(9) . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C2 1.3900 . ?
C8 C9 1.413(11) . ?
C9 C10 1.434(11) . ?
C9 C12 1.406(11) . ?
C10 H10 0.9500 . ?
C10 C11 1.345(12) . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.492(9) . ?
C18 C17 1.3900 . ?
C18 C19 1.3900 . ?
C18 C21 1.467(9) . ?
C17 C16 1.3900 . ?
C16 H16 0.9500 . ?
C16 C15 1.3900 . ?
C15 C20 1.3900 . ?
C20 H20 0.9500 . ?
C20 C19 1.3900 . ?
C19 H19 0.9500 . ?
C21 C22 1.403(11) . ?
C22 C23 1.420(11) . ?
C22 C25 1.413(11) . ?
C23 H23 0.9500 . ?
C23 C24 1.369(12) . ?
C24 H24 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.508(11) . ?
C28 C29 1.361(11) . ?
C29 H29 0.9500 . ?
C29 C30 1.396(12) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 O1 94.4(2) . . ?
N1 Ir1 N3 176.4(2) . . ?
N1 Ir1 N5 89.0(2) . . ?
N3 Ir1 O1 85.5(2) . . ?
N3 Ir1 N5 94.5(2) . . ?
N5 Ir1 O1 77.0(2) . . ?
C6 Ir1 O1 172.56(19) . . ?
C6 Ir1 N1 79.6(2) . . ?
C6 Ir1 N3 100.7(2) . . ?
C6 Ir1 N5 98.2(2) . . ?
C6 Ir1 C17 88.6(2) . . ?
C17 Ir1 O1 96.6(2) . . ?
C17 Ir1 N1 96.7(2) . . ?
C17 Ir1 N3 79.7(2) . . ?
C17 Ir1 N5 171.8(2) . . ?
C11 S1 C12 90.4(4) . . ?
C24 S2 C25 90.8(4) . . ?
C27 O1 Ir1 115.5(5) . . ?
C8 N1 Ir1 117.4(5) . . ?
C13 N1 Ir1 121.9(5) . . ?
C13 N1 C8 120.6(7) . . ?
C13 N2 C12 113.9(7) . . ?
C21 N3 Ir1 115.5(5) . . ?
C26 N3 Ir1 124.7(5) . . ?
C26 N3 C21 119.4(7) . . ?
C26 N4 C25 112.9(7) . . ?
C28 N5 Ir1 113.8(5) . . ?
C31 N5 Ir1 127.7(5) . . ?
C31 N5 C28 118.2(7) . . ?
C31 N6 C30 115.6(7) . . ?
F1 C1 F3 106.4(7) . . ?
F1 C1 C2 113.3(7) . . ?
F2 C1 F1 106.4(7) . . ?
F2 C1 F3 107.0(7) . . ?
F2 C1 C2 111.7(7) . . ?
F3 C1 C2 111.7(7) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C2 120.0 . . ?
C2 C7 H7 120.0 . . ?
C7 C6 Ir1 125.8(2) . . ?
C5 C6 Ir1 114.0(2) . . ?
C5 C6 C7 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 117.0(4) . . ?
C4 C5 C8 122.7(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C7 C2 C1 118.5(4) . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 C7 120.0 . . ?
N1 C8 C5 111.7(6) . . ?
N1 C8 C9 117.4(7) . . ?
C9 C8 C5 130.7(7) . . ?
C8 C9 C10 134.1(8) . . ?
C12 C9 C8 115.4(8) . . ?
C12 C9 C10 110.5(7) . . ?
C9 C10 H10 123.3 . . ?
C11 C10 C9 113.4(8) . . ?
C11 C10 H10 123.3 . . ?
S1 C11 H11 123.1 . . ?
C10 C11 S1 113.8(7) . . ?
C10 C11 H11 123.1 . . ?
N2 C12 S1 121.5(6) . . ?
N2 C12 C9 126.6(7) . . ?
C9 C12 S1 111.9(6) . . ?
N1 C13 H13 117.2 . . ?
N2 C13 N1 125.7(8) . . ?
N2 C13 H13 117.2 . . ?
F4 C14 F6 105.2(7) . . ?
F4 C14 C15 111.4(6) . . ?
F5 C14 F4 107.3(7) . . ?
F5 C14 F6 107.0(7) . . ?
F5 C14 C15 113.6(7) . . ?
F6 C14 C15 111.8(6) . . ?
C17 C18 C19 120.0 . . ?
C17 C18 C21 116.8(4) . . ?
C19 C18 C21 123.0(4) . . ?
C18 C17 Ir1 113.4(2) . . ?
C16 C17 Ir1 126.6(2) . . ?
C16 C17 C18 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 C14 120.2(4) . . ?
C20 C15 C14 119.8(4) . . ?
C20 C15 C16 120.0 . . ?
C15 C20 H20 120.0 . . ?
C15 C20 C19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
N3 C21 C18 112.4(6) . . ?
N3 C21 C22 118.3(7) . . ?
C22 C21 C18 129.3(7) . . ?
C21 C22 C23 133.0(7) . . ?
C21 C22 C25 115.4(7) . . ?
C25 C22 C23 111.5(7) . . ?
C22 C23 H23 124.0 . . ?
C24 C23 C22 111.9(8) . . ?
C24 C23 H23 124.0 . . ?
S2 C24 H24 123.1 . . ?
C23 C24 S2 113.9(7) . . ?
C23 C24 H24 123.1 . . ?
N4 C25 S2 122.2(6) . . ?
N4 C25 C22 126.0(7) . . ?
C22 C25 S2 111.8(6) . . ?
N3 C26 H26 116.3 . . ?
N4 C26 N3 127.5(8) . . ?
N4 C26 H26 116.3 . . ?
O1 C27 C28 116.8(6) . . ?
O2 C27 O1 125.3(8) . . ?
O2 C27 C28 117.8(7) . . ?
N5 C28 C27 115.7(7) . . ?
N5 C28 C29 120.2(7) . . ?
C29 C28 C27 124.0(7) . . ?
C28 C29 H29 121.3 . . ?
C28 C29 C30 117.4(7) . . ?
C30 C29 H29 121.3 . . ?
N6 C30 C29 122.8(8) . . ?
N6 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
N5 C31 N6 125.7(8) . . ?
N5 C31 H31 117.2 . . ?
N6 C31 H31 117.2 . . ?

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
Ir1 O1 C27 O2 168.2(7) . . . . ?
Ir1 O1 C27 C28 -11.2(9) . . . . ?
Ir1 N1 C8 C5 -4.1(8) . . . . ?
Ir1 N1 C8 C9 -179.7(5) . . . . ?
Ir1 N1 C13 N2 173.1(6) . . . . ?
Ir1 N3 C21 C18 15.8(8) . . . . ?
Ir1 N3 C21 C22 -167.0(6) . . . . ?
Ir1 N3 C26 N4 171.9(6) . . . . ?
Ir1 N5 C28 C27 -4.5(8) . . . . ?
Ir1 N5 C28 C29 174.1(6) . . . . ?
Ir1 N5 C31 N6 -170.7(6) . . . . ?
Ir1 C6 C5 C4 176.2(3) . . . . ?
Ir1 C6 C5 C8 2.5(5) . . . . ?
Ir1 C17 C16 C15 177.8(4) . . . . ?
F1 C1 C2 C7 178.8(5) . . . . ?
F1 C1 C2 C3 -3.1(9) . . . . ?
F2 C1 C2 C7 58.6(8) . . . . ?
F2 C1 C2 C3 -123.3(6) . . . . ?
F3 C1 C2 C7 -61.2(8) . . . . ?
F3 C1 C2 C3 116.9(6) . . . . ?
F4 C14 C15 C16 40.6(8) . . . . ?
F4 C14 C15 C20 -141.3(5) . . . . ?
F5 C14 C15 C16 162.0(5) . . . . ?
F5 C14 C15 C20 -20.0(9) . . . . ?
F6 C14 C15 C16 -76.8(8) . . . . ?
F6 C14 C15 C20 101.3(7) . . . . ?
O1 C27 C28 N5 10.7(10) . . . . ?
O1 C27 C28 C29 -167.8(8) . . . . ?
O2 C27 C28 N5 -168.7(7) . . . . ?
O2 C27 C28 C29 12.7(12) . . . . ?
N1 C8 C9 C10 -176.3(9) . . . . ?
N1 C8 C9 C12 6.5(10) . . . . ?
N3 C21 C22 C23 173.0(8) . . . . ?
N3 C21 C22 C25 -6.2(11) . . . . ?
N5 C28 C29 C30 -2.3(12) . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C7 C6 C5 C8 -173.7(5) . . . . ?
C6 C7 C2 C1 178.2(6) . . . . ?
C6 C7 C2 C3 0.0 . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C5 C8 N1 1.0(8) . . . . ?
C6 C5 C8 C9 175.8(7) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C5 C8 C9 C10 9.1(15) . . . . ?
C5 C8 C9 C12 -168.1(7) . . . . ?
C4 C5 C8 N1 -172.5(5) . . . . ?
C4 C5 C8 C9 2.3(11) . . . . ?
C4 C3 C2 C1 -178.1(6) . . . . ?
C4 C3 C2 C7 0.0 . . . . ?
C2 C7 C6 Ir1 -175.7(4) . . . . ?
C2 C7 C6 C5 0.0 . . . . ?
C8 N1 C13 N2 -3.0(12) . . . . ?
C8 C5 C4 C3 173.3(6) . . . . ?
C8 C9 C10 C11 -174.5(9) . . . . ?
C8 C9 C12 S1 174.2(6) . . . . ?
C8 C9 C12 N2 -4.5(12) . . . . ?
C9 C10 C11 S1 -0.6(10) . . . . ?
C10 C9 C12 S1 -3.6(9) . . . . ?
C10 C9 C12 N2 177.7(8) . . . . ?
C11 S1 C12 N2 -178.5(7) . . . . ?
C11 S1 C12 C9 2.8(6) . . . . ?
C12 S1 C11 C10 -1.2(7) . . . . ?
C12 N2 C13 N1 5.3(12) . . . . ?
C12 C9 C10 C11 2.7(11) . . . . ?
C13 N1 C8 C5 172.2(6) . . . . ?
C13 N1 C8 C9 -3.4(11) . . . . ?
C13 N2 C12 S1 -179.9(6) . . . . ?
C13 N2 C12 C9 -1.3(12) . . . . ?
C14 C15 C20 C19 -178.1(6) . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C18 C21 C22 C23 -10.3(15) . . . . ?
C18 C21 C22 C25 170.5(7) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C17 C18 C21 N3 -8.7(8) . . . . ?
C17 C18 C21 C22 174.4(7) . . . . ?
C17 C16 C15 C14 178.0(6) . . . . ?
C17 C16 C15 C20 0.0 . . . . ?
C16 C15 C20 C19 0.0 . . . . ?
C15 C20 C19 C18 0.0 . . . . ?
C19 C18 C17 Ir1 -178.1(3) . . . . ?
C19 C18 C17 C16 0.0 . . . . ?
C19 C18 C21 N3 166.7(5) . . . . ?
C19 C18 C21 C22 -10.1(10) . . . . ?
C21 N3 C26 N4 -0.4(13) . . . . ?
C21 C18 C17 Ir1 -2.5(5) . . . . ?
C21 C18 C17 C16 175.6(5) . . . . ?
C21 C18 C19 C20 -175.3(6) . . . . ?
C21 C22 C23 C24 178.6(9) . . . . ?
C21 C22 C25 S2 -179.7(6) . . . . ?
C21 C22 C25 N4 1.3(12) . . . . ?
C22 C23 C24 S2 2.4(10) . . . . ?
C23 C22 C25 S2 0.9(9) . . . . ?
C23 C22 C25 N4 -178.1(8) . . . . ?
C24 S2 C25 N4 179.4(7) . . . . ?
C24 S2 C25 C22 0.3(7) . . . . ?
C25 S2 C24 C23 -1.6(8) . . . . ?
C25 N4 C26 N3 -4.4(12) . . . . ?
C25 C22 C23 C24 -2.1(10) . . . . ?
C26 N3 C21 C18 -171.2(6) . . . . ?
C26 N3 C21 C22 6.0(11) . . . . ?
C26 N4 C25 S2 -175.1(6) . . . . ?
C26 N4 C25 C22 3.8(12) . . . . ?
C27 C28 C29 C30 176.3(8) . . . . ?
C28 N5 C31 N6 4.0(12) . . . . ?
C28 C29 C30 N6 3.8(13) . . . . ?
C30 N6 C31 N5 -2.6(12) . . . . ?
C31 N5 C28 C27 -180.0(7) . . . . ?
C31 N5 C28 C29 -1.3(11) . . . . ?
C31 N6 C30 C29 -1.4(12) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2302907'
_audit_update_record             
;
2023-10-23 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2023-09-11
_diffrn_source_power             0.0705
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C35 H19 F6 Ir N6 O2'
_chemical_formula_moiety         'C35 H19 F6 Ir N6 O2'
_exptl_crystal_colour_primary    red
_chemical_formula_weight         861.76
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C13(H13), C22(H22), C25(H25), C10(H10), C31(H31), C30(H30), C24(H24),
 C32(H32), C18(H18), C11(H11), C6(H6), C20(H20), C5(H5), C19(H19), C34(H34),
 C3(H3), C33(H33), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   23.8664(14)
_cell_length_b                   15.4400(8)
_cell_length_c                   17.1443(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.336(2)
_cell_angle_gamma                90
_cell_volume                     6194.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.29
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_F_000             3344
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    4.392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1413
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.5379.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.362
_shelx_estimated_absorpt_T_max   0.474
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.41
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            57126
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7701
_reflns_number_gt                6619
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS V6.2.16/2021-10-22 && APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0220P)²+14.4053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         7701
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0516
_refine_ls_wR_factor_gt          0.0487
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.126
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
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'

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

loop_
_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 0.67823(2) 0.69640(2) 0.23848(2) 0.01593(4) Uani 1 1 d . . . . .
O1 O 0.65623(8) 0.80628(11) 0.16139(11) 0.0206(4) Uani 1 1 d . . . . .
F4 F 0.66356(10) 0.45449(13) 0.51694(11) 0.0445(5) Uani 1 1 d . . . . .
F3 F 0.91029(9) 0.87097(14) 0.28002(15) 0.0553(6) Uani 1 1 d . . . . .
O2 O 0.58637(9) 0.86113(13) 0.06802(12) 0.0271(4) Uani 1 1 d . . . . .
F6 F 0.63723(10) 0.34764(13) 0.44028(12) 0.0483(5) Uani 1 1 d . . . . .
N1 N 0.63808(10) 0.75773(14) 0.31747(13) 0.0191(4) Uani 1 1 d . . . . .
F1 F 0.91381(9) 0.73395(14) 0.28934(14) 0.0520(6) Uani 1 1 d . . . . .
F2 F 0.94176(9) 0.81167(16) 0.39189(13) 0.0563(6) Uani 1 1 d . . . . .
N3 N 0.60451(9) 0.65317(14) 0.15632(12) 0.0181(4) Uani 1 1 d . . . . .
N5 N 0.73129(9) 0.63707(14) 0.17472(12) 0.0189(4) Uani 1 1 d . . . . .
C21 C 0.69422(11) 0.58641(17) 0.29915(14) 0.0174(5) Uani 1 1 d . . . . .
F5 F 0.58791(9) 0.46518(17) 0.42802(14) 0.0644(7) Uani 1 1 d . . . . .
N2 N 0.55183(10) 0.79649(15) 0.35827(14) 0.0239(5) Uani 1 1 d . . . . .
C14 C 0.74473(11) 0.75309(16) 0.30878(15) 0.0187(5) Uani 1 1 d . . . . .
N6 N 0.79231(11) 0.65343(16) 0.08151(14) 0.0268(5) Uani 1 1 d . . . . .
N4 N 0.53833(11) 0.54768(15) 0.09393(14) 0.0275(5) Uani 1 1 d . . . . .
C26 C 0.73537(11) 0.53197(16) 0.27412(15) 0.0185(5) Uani 1 1 d . . . . .
C8 C 0.67111(12) 0.80086(16) 0.37845(15) 0.0190(5) Uani 1 1 d . . . . .
C1 C 0.58013(12) 0.75786(18) 0.31098(16) 0.0224(5) Uani 1 1 d . . . . .
H1 H 0.558401 0.726619 0.267625 0.027 Uiso 1 1 calc R U . . .
C13 C 0.80112(12) 0.75372(17) 0.29742(16) 0.0208(5) Uani 1 1 d . . . . .
H13 H 0.811147 0.718560 0.256801 0.025 Uiso 1 1 calc R U . . .
C27 C 0.76133(11) 0.56944(17) 0.21125(15) 0.0196(5) Uani 1 1 d . . . . .
C9 C 0.73162(12) 0.80457(17) 0.37157(16) 0.0218(5) Uani 1 1 d . . . . .
C16 C 0.60929(11) 0.80177(17) 0.10994(15) 0.0190(5) Uani 1 1 d . . . . .
C22 C 0.66497(12) 0.55274(17) 0.35546(15) 0.0209(5) Uani 1 1 d . . . . .
H22 H 0.637915 0.587785 0.374706 0.025 Uiso 1 1 calc R U . . .
C7 C 0.64460(12) 0.83673(17) 0.43867(16) 0.0219(5) Uani 1 1 d . . . . .
C25 C 0.74522(12) 0.44753(17) 0.30305(16) 0.0235(6) Uani 1 1 d . . . . .
H25 H 0.772442 0.411864 0.284853 0.028 Uiso 1 1 calc R U . . .
C10 C 0.77362(13) 0.8590(2) 0.41520(17) 0.0290(6) Uani 1 1 d . . . . .
H10 H 0.763980 0.896709 0.454296 0.035 Uiso 1 1 calc R U . . .
C2 C 0.58373(12) 0.83624(18) 0.42411(16) 0.0224(6) Uani 1 1 d . . . . .
C12 C 0.84266(12) 0.80408(18) 0.34366(17) 0.0235(6) Uani 1 1 d . . . . .
C23 C 0.67502(12) 0.46842(18) 0.38372(16) 0.0227(6) Uani 1 1 d . . . . .
C31 C 0.85667(12) 0.49377(18) 0.23584(17) 0.0248(6) Uani 1 1 d . . . . .
H31 H 0.847865 0.461982 0.279331 0.030 Uiso 1 1 calc R U . . .
C30 C 0.74720(13) 0.67325(18) 0.10935(15) 0.0234(6) Uani 1 1 d . . . . .
H30 H 0.722945 0.716853 0.081904 0.028 Uiso 1 1 calc R U . . .
C17 C 0.58164(11) 0.71257(16) 0.10152(15) 0.0181(5) Uani 1 1 d . . . . .
C29 C 0.82871(12) 0.59389(19) 0.12430(16) 0.0251(6) Uani 1 1 d . . . . .
C24 C 0.71516(12) 0.41618(18) 0.35824(16) 0.0251(6) Uani 1 1 d . . . . .
H24 H 0.721966 0.359112 0.378615 0.030 Uiso 1 1 calc R U . . .
C32 C 0.90984(13) 0.48699(19) 0.21721(19) 0.0295(6) Uani 1 1 d . . . . .
H32 H 0.938301 0.452531 0.249456 0.035 Uiso 1 1 calc R U . . .
C18 C 0.53629(12) 0.69087(18) 0.04143(16) 0.0226(5) Uani 1 1 d . . . . .
H18 H 0.519623 0.732109 0.002610 0.027 Uiso 1 1 calc R U . . .
C28 C 0.81476(12) 0.54847(17) 0.18993(16) 0.0220(5) Uani 1 1 d . . . . .
C11 C 0.82895(13) 0.8580(2) 0.40168(17) 0.0298(7) Uani 1 1 d . . . . .
H11 H 0.857327 0.894187 0.432028 0.036 Uiso 1 1 calc R U . . .
C6 C 0.67365(13) 0.8725(2) 0.51182(17) 0.0296(6) Uani 1 1 d . . . . .
H6 H 0.714132 0.869067 0.525719 0.035 Uiso 1 1 calc R U . . .
C20 C 0.58188(12) 0.57353(17) 0.15027(16) 0.0228(6) Uani 1 1 d . . . . .
H20 H 0.598149 0.532154 0.189205 0.027 Uiso 1 1 calc R U . . .
C5 C 0.64390(14) 0.9116(2) 0.56226(17) 0.0343(7) Uani 1 1 d . . . . .
H5 H 0.664123 0.936168 0.610447 0.041 Uiso 1 1 calc R U . . .
C15 C 0.90195(13) 0.80445(19) 0.32662(18) 0.0280(6) Uani 1 1 d . . . . .
C19 C 0.51605(12) 0.60683(19) 0.03990(17) 0.0273(6) Uani 1 1 d . . . . .
H19 H 0.485059 0.590568 -0.001240 0.033 Uiso 1 1 calc R U . . .
C34 C 0.88286(14) 0.5819(2) 0.10400(19) 0.0326(7) Uani 1 1 d . . . . .
H34 H 0.891579 0.609324 0.058219 0.039 Uiso 1 1 calc R U . . .
C35 C 0.64065(14) 0.4337(2) 0.44089(18) 0.0302(7) Uani 1 1 d . . . . .
C3 C 0.55403(13) 0.87786(18) 0.47706(17) 0.0263(6) Uani 1 1 d . . . . .
H3 H 0.513438 0.879124 0.465979 0.032 Uiso 1 1 calc R U . . .
C33 C 0.92258(14) 0.5305(2) 0.1509(2) 0.0339(7) Uani 1 1 d . . . . .
H33 H 0.959412 0.524242 0.138359 0.041 Uiso 1 1 calc R U . . .
C4 C 0.58394(14) 0.9164(2) 0.54442(17) 0.0311(7) Uani 1 1 d . . . . .
H4 H 0.564149 0.946387 0.579146 0.037 Uiso 1 1 calc R U . . .


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 O1 2.1513(18) . ?
Ir1 N1 2.039(2) . ?
Ir1 N3 2.133(2) . ?
Ir1 N5 2.045(2) . ?
Ir1 C21 1.989(3) . ?
Ir1 C14 1.996(3) . ?
O1 C16 1.284(3) . ?
F4 C35 1.350(4) . ?
F3 C15 1.340(4) . ?
O2 C16 1.225(3) . ?
F6 C35 1.331(4) . ?
N1 C8 1.354(3) . ?
N1 C1 1.366(4) . ?
F1 C15 1.321(3) . ?
F2 C15 1.323(3) . ?
N3 C17 1.349(3) . ?
N3 C20 1.339(3) . ?
N5 C27 1.349(3) . ?
N5 C30 1.371(3) . ?
C21 C26 1.422(4) . ?
C21 C22 1.398(4) . ?
F5 C35 1.327(4) . ?
N2 C1 1.298(4) . ?
N2 C2 1.376(3) . ?
C14 C13 1.397(4) . ?
C14 C9 1.422(4) . ?
N6 C30 1.297(4) . ?
N6 C29 1.374(4) . ?
N4 C20 1.333(3) . ?
N4 C19 1.335(4) . ?
C26 C27 1.464(4) . ?
C26 C25 1.398(4) . ?
C8 C9 1.473(4) . ?
C8 C7 1.425(4) . ?
C1 H1 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.381(4) . ?
C27 C28 1.431(4) . ?
C9 C10 1.405(4) . ?
C16 C17 1.522(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.393(4) . ?
C7 C2 1.425(4) . ?
C7 C6 1.420(4) . ?
C25 H25 0.9500 . ?
C25 C24 1.382(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(4) . ?
C2 C3 1.412(4) . ?
C12 C11 1.385(4) . ?
C12 C15 1.500(4) . ?
C23 C24 1.387(4) . ?
C23 C35 1.496(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.372(4) . ?
C31 C28 1.423(4) . ?
C30 H30 0.9500 . ?
C17 C18 1.381(4) . ?
C29 C28 1.420(4) . ?
C29 C34 1.415(4) . ?
C24 H24 0.9500 . ?
C32 H32 0.9500 . ?
C32 C33 1.405(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(4) . ?
C11 H11 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.363(4) . ?
C20 H20 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.405(4) . ?
C19 H19 0.9500 . ?
C34 H34 0.9500 . ?
C34 C33 1.369(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.369(4) . ?
C33 H33 0.9500 . ?
C4 H4 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 O1 87.25(8) . . ?
N1 Ir1 N3 98.61(8) . . ?
N1 Ir1 N5 169.77(9) . . ?
N3 Ir1 O1 76.77(8) . . ?
N5 Ir1 O1 97.29(8) . . ?
N5 Ir1 N3 91.37(8) . . ?
C21 Ir1 O1 173.35(8) . . ?
C21 Ir1 N1 96.67(9) . . ?
C21 Ir1 N3 97.28(9) . . ?
C21 Ir1 N5 79.73(10) . . ?
C21 Ir1 C14 90.61(10) . . ?
C14 Ir1 O1 95.40(9) . . ?
C14 Ir1 N1 79.46(10) . . ?
C14 Ir1 N3 172.06(9) . . ?
C14 Ir1 N5 90.96(10) . . ?
C16 O1 Ir1 116.99(16) . . ?
C8 N1 Ir1 117.57(18) . . ?
C8 N1 C1 119.2(2) . . ?
C1 N1 Ir1 123.17(17) . . ?
C17 N3 Ir1 114.54(17) . . ?
C20 N3 Ir1 127.33(18) . . ?
C20 N3 C17 117.9(2) . . ?
C27 N5 Ir1 115.28(17) . . ?
C27 N5 C30 119.2(2) . . ?
C30 N5 Ir1 123.68(18) . . ?
C26 C21 Ir1 114.83(18) . . ?
C22 C21 Ir1 127.5(2) . . ?
C22 C21 C26 117.2(2) . . ?
C1 N2 C2 116.5(2) . . ?
C13 C14 Ir1 126.31(19) . . ?
C13 C14 C9 117.6(2) . . ?
C9 C14 Ir1 115.79(19) . . ?
C30 N6 C29 116.4(2) . . ?
C20 N4 C19 116.4(2) . . ?
C21 C26 C27 114.0(2) . . ?
C25 C26 C21 121.5(2) . . ?
C25 C26 C27 124.3(2) . . ?
N1 C8 C9 112.8(2) . . ?
N1 C8 C7 118.5(2) . . ?
C7 C8 C9 128.7(2) . . ?
N1 C1 H1 116.8 . . ?
N2 C1 N1 126.4(3) . . ?
N2 C1 H1 116.8 . . ?
C14 C13 H13 119.1 . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 H13 119.1 . . ?
N5 C27 C26 112.6(2) . . ?
N5 C27 C28 118.4(2) . . ?
C28 C27 C26 128.8(2) . . ?
C14 C9 C8 113.8(2) . . ?
C10 C9 C14 119.8(3) . . ?
C10 C9 C8 126.1(3) . . ?
O1 C16 C17 114.7(2) . . ?
O2 C16 O1 126.2(2) . . ?
O2 C16 C17 119.1(2) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C8 C7 C2 117.0(2) . . ?
C6 C7 C8 125.6(3) . . ?
C6 C7 C2 117.4(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.1 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
N2 C2 C7 121.8(2) . . ?
N2 C2 C3 117.6(3) . . ?
C3 C2 C7 120.6(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 C15 119.2(3) . . ?
C11 C12 C15 120.2(3) . . ?
C22 C23 C35 118.9(3) . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 C35 120.0(2) . . ?
C32 C31 H31 120.1 . . ?
C32 C31 C28 119.9(3) . . ?
C28 C31 H31 120.1 . . ?
N5 C30 H30 117.0 . . ?
N6 C30 N5 126.0(3) . . ?
N6 C30 H30 117.0 . . ?
N3 C17 C16 116.1(2) . . ?
N3 C17 C18 120.3(2) . . ?
C18 C17 C16 123.5(2) . . ?
N6 C29 C28 122.1(3) . . ?
N6 C29 C34 117.9(3) . . ?
C34 C29 C28 119.9(3) . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C31 C32 H32 119.7 . . ?
C31 C32 C33 120.6(3) . . ?
C33 C32 H32 119.7 . . ?
C17 C18 H18 121.3 . . ?
C17 C18 C19 117.5(3) . . ?
C19 C18 H18 121.3 . . ?
C31 C28 C27 123.9(3) . . ?
C29 C28 C27 116.8(3) . . ?
C29 C28 C31 118.9(3) . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
N3 C20 H20 117.4 . . ?
N4 C20 N3 125.2(3) . . ?
N4 C20 H20 117.4 . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
F3 C15 C12 112.0(2) . . ?
F1 C15 F3 105.8(3) . . ?
F1 C15 F2 107.0(3) . . ?
F1 C15 C12 113.0(2) . . ?
F2 C15 F3 105.9(3) . . ?
F2 C15 C12 112.6(3) . . ?
N4 C19 C18 122.6(3) . . ?
N4 C19 H19 118.7 . . ?
C18 C19 H19 118.7 . . ?
C29 C34 H34 120.3 . . ?
C33 C34 C29 119.5(3) . . ?
C33 C34 H34 120.3 . . ?
F4 C35 C23 112.2(3) . . ?
F6 C35 F4 104.9(2) . . ?
F6 C35 C23 113.2(3) . . ?
F5 C35 F4 105.3(3) . . ?
F5 C35 F6 108.1(3) . . ?
F5 C35 C23 112.6(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C32 C33 H33 119.4 . . ?
C34 C33 C32 121.2(3) . . ?
C34 C33 H33 119.4 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ir1 O1 C16 O2 170.5(2) . . . . ?
Ir1 O1 C16 C17 -10.5(3) . . . . ?
Ir1 N1 C8 C9 6.9(3) . . . . ?
Ir1 N1 C8 C7 -173.78(18) . . . . ?
Ir1 N1 C1 N2 -178.9(2) . . . . ?
Ir1 N3 C17 C16 -3.7(3) . . . . ?
Ir1 N3 C17 C18 175.4(2) . . . . ?
Ir1 N3 C20 N4 -174.5(2) . . . . ?
Ir1 N5 C27 C26 21.4(3) . . . . ?
Ir1 N5 C27 C28 -153.42(19) . . . . ?
Ir1 N5 C30 N6 157.6(2) . . . . ?
Ir1 C21 C26 C27 3.7(3) . . . . ?
Ir1 C21 C26 C25 -170.8(2) . . . . ?
Ir1 C21 C22 C23 169.5(2) . . . . ?
Ir1 C14 C13 C12 171.5(2) . . . . ?
Ir1 C14 C9 C8 5.3(3) . . . . ?
Ir1 C14 C9 C10 -168.8(2) . . . . ?
O1 C16 C17 N3 9.5(3) . . . . ?
O1 C16 C17 C18 -169.5(2) . . . . ?
O2 C16 C17 N3 -171.4(2) . . . . ?
O2 C16 C17 C18 9.5(4) . . . . ?
N1 C8 C9 C14 -7.8(3) . . . . ?
N1 C8 C9 C10 165.8(3) . . . . ?
N1 C8 C7 C2 -9.4(4) . . . . ?
N1 C8 C7 C6 170.3(3) . . . . ?
N3 C17 C18 C19 -0.3(4) . . . . ?
N5 C27 C28 C31 164.3(2) . . . . ?
N5 C27 C28 C29 -7.8(4) . . . . ?
C21 C26 C27 N5 -16.4(3) . . . . ?
C21 C26 C27 C28 157.8(3) . . . . ?
C21 C26 C25 C24 -1.1(4) . . . . ?
C21 C22 C23 C24 1.5(4) . . . . ?
C21 C22 C23 C35 -177.0(3) . . . . ?
N2 C2 C3 C4 178.3(3) . . . . ?
C14 C13 C12 C11 -2.0(4) . . . . ?
C14 C13 C12 C15 -177.8(3) . . . . ?
C14 C9 C10 C11 -5.0(4) . . . . ?
N6 C29 C28 C27 -1.8(4) . . . . ?
N6 C29 C28 C31 -174.3(2) . . . . ?
N6 C29 C34 C33 172.7(3) . . . . ?
C26 C21 C22 C23 -1.7(4) . . . . ?
C26 C27 C28 C31 -9.6(4) . . . . ?
C26 C27 C28 C29 178.3(3) . . . . ?
C26 C25 C24 C23 0.8(4) . . . . ?
C8 N1 C1 N2 0.4(4) . . . . ?
C8 C9 C10 C11 -178.2(3) . . . . ?
C8 C7 C2 N2 5.4(4) . . . . ?
C8 C7 C2 C3 -173.9(3) . . . . ?
C8 C7 C6 C5 174.5(3) . . . . ?
C1 N1 C8 C9 -172.4(2) . . . . ?
C1 N1 C8 C7 6.9(4) . . . . ?
C1 N2 C2 C7 1.4(4) . . . . ?
C1 N2 C2 C3 -179.3(3) . . . . ?
C13 C14 C9 C8 179.2(2) . . . . ?
C13 C14 C9 C10 5.2(4) . . . . ?
C13 C12 C11 C10 2.3(4) . . . . ?
C13 C12 C15 F3 95.7(3) . . . . ?
C13 C12 C15 F1 -23.7(4) . . . . ?
C13 C12 C15 F2 -145.1(3) . . . . ?
C27 N5 C30 N6 -6.1(4) . . . . ?
C27 C26 C25 C24 -175.0(3) . . . . ?
C9 C14 C13 C12 -1.8(4) . . . . ?
C9 C8 C7 C2 169.7(3) . . . . ?
C9 C8 C7 C6 -10.6(5) . . . . ?
C9 C10 C11 C12 1.1(5) . . . . ?
C16 C17 C18 C19 178.7(3) . . . . ?
C22 C21 C26 C27 176.0(2) . . . . ?
C22 C21 C26 C25 1.6(4) . . . . ?
C22 C23 C24 C25 -0.9(4) . . . . ?
C22 C23 C35 F4 -85.8(3) . . . . ?
C22 C23 C35 F6 155.7(3) . . . . ?
C22 C23 C35 F5 32.8(4) . . . . ?
C7 C8 C9 C14 173.0(3) . . . . ?
C7 C8 C9 C10 -13.4(5) . . . . ?
C7 C2 C3 C4 -2.3(4) . . . . ?
C7 C6 C5 C4 1.2(5) . . . . ?
C25 C26 C27 N5 157.9(2) . . . . ?
C25 C26 C27 C28 -27.9(4) . . . . ?
C2 N2 C1 N1 -4.6(4) . . . . ?
C2 C7 C6 C5 -5.8(4) . . . . ?
C2 C3 C4 C5 -2.4(5) . . . . ?
C31 C32 C33 C34 1.1(5) . . . . ?
C30 N5 C27 C26 -173.5(2) . . . . ?
C30 N5 C27 C28 11.6(3) . . . . ?
C30 N6 C29 C28 7.4(4) . . . . ?
C30 N6 C29 C34 -169.2(3) . . . . ?
C17 N3 C20 N4 0.2(4) . . . . ?
C17 C18 C19 N4 0.5(4) . . . . ?
C29 N6 C30 N5 -3.6(4) . . . . ?
C29 C34 C33 C32 2.3(5) . . . . ?
C24 C23 C35 F4 95.8(3) . . . . ?
C24 C23 C35 F6 -22.7(4) . . . . ?
C24 C23 C35 F5 -145.6(3) . . . . ?
C32 C31 C28 C27 -170.7(3) . . . . ?
C32 C31 C28 C29 1.2(4) . . . . ?
C28 C31 C32 C33 -2.9(4) . . . . ?
C28 C29 C34 C33 -3.9(4) . . . . ?
C11 C12 C15 F3 -80.1(3) . . . . ?
C11 C12 C15 F1 160.5(3) . . . . ?
C11 C12 C15 F2 39.1(4) . . . . ?
C6 C7 C2 N2 -174.4(3) . . . . ?
C6 C7 C2 C3 6.4(4) . . . . ?
C6 C5 C4 C3 3.0(5) . . . . ?
C20 N3 C17 C16 -179.1(2) . . . . ?
C20 N3 C17 C18 0.0(4) . . . . ?
C20 N4 C19 C18 -0.3(4) . . . . ?
C15 C12 C11 C10 178.1(3) . . . . ?
C19 N4 C20 N3 -0.1(4) . . . . ?
C34 C29 C28 C27 174.7(3) . . . . ?
C34 C29 C28 C31 2.2(4) . . . . ?
C35 C23 C24 C25 177.5(3) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2302906'
_audit_update_record             
;
2023-10-23 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2023-09-11
_diffrn_source_power             0.07
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C33 H21 Ir N6 O2'
_chemical_formula_moiety         'C33 H21 Ir N6 O2'
_exptl_crystal_colour_primary    red
_chemical_formula_weight         725.76
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C28-H28
 0.95 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14), C15(H15),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C29(H29), C30(H30), C31(H31), C32(H32)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.1167(11)
_cell_length_b                   17.0189(5)
_cell_length_c                   18.3944(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.640(4)
_cell_angle_gamma                90
_cell_volume                     5184.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9656
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.97
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    5.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1621
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1237 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.6171.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            31182
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_theta_min         2.289
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6465
_reflns_number_gt                4121
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+37.3805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         6465
_refine_ls_number_parameters     383
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.633
_refine_diff_density_min         -1.184
_refine_diff_density_rms         0.165
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
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'

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

loop_
_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 0.50155(2) 0.25175(2) 0.54515(2) 0.01951(7) Uani 1 1 d . . . . .
O1 O 0.4473(2) 0.1873(2) 0.4430(2) 0.0242(9) Uani 1 1 d . . . . .
O2 O 0.4546(3) 0.0744(3) 0.3818(3) 0.0333(11) Uani 1 1 d . . . . .
N1 N 0.4296(3) 0.2017(3) 0.6045(3) 0.0229(11) Uani 1 1 d . . . . .
N2 N 0.3156(3) 0.1217(3) 0.6029(3) 0.0326(13) Uani 1 1 d . . . . .
N3 N 0.5764(3) 0.1493(3) 0.5525(3) 0.0265(11) Uani 1 1 d . . . . .
N4 N 0.6924(3) 0.0717(3) 0.6059(3) 0.0336(13) Uani 1 1 d . . . . .
N5 N 0.5612(3) 0.3120(3) 0.4791(3) 0.0234(11) Uani 1 1 d . . . . .
N6 N 0.6694(3) 0.3249(3) 0.4192(3) 0.0299(12) Uani 1 1 d . . . . .
C1 C 0.4796(4) 0.1215(3) 0.4334(3) 0.0248(13) Uani 1 1 d . . . . .
C2 C 0.2679(4) 0.1091(4) 0.7140(4) 0.0339(16) Uani 1 1 d . . . . .
H2 H 0.231180 0.069758 0.689511 0.041 Uiso 1 1 calc R U . . .
C3 C 0.5290(4) 0.4777(4) 0.2619(4) 0.0345(15) Uani 1 1 d . . . . .
H3 H 0.497718 0.511409 0.224487 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5180(4) 0.3695(3) 0.4369(3) 0.0228(13) Uani 1 1 d . . . . .
C5 C 0.4334(3) 0.3476(3) 0.5227(3) 0.0204(12) Uani 1 1 d . . . . .
C6 C 0.3666(4) 0.1545(3) 0.5707(4) 0.0262(14) Uani 1 1 d . . . . .
H6 H 0.359203 0.144623 0.518615 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6042(4) 0.0376(4) 0.4873(4) 0.0314(15) Uani 1 1 d . . . . .
H7 H 0.591106 0.003709 0.444923 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2675(4) 0.1325(4) 0.7839(4) 0.0328(15) Uani 1 1 d . . . . .
H8 H 0.231511 0.108477 0.808889 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5443(4) 0.3994(3) 0.3743(4) 0.0254(13) Uani 1 1 d . . . . .
C10 C 0.4505(3) 0.3966(3) 0.4656(3) 0.0203(12) Uani 1 1 d . . . . .
C11 C 0.6220(4) 0.3765(4) 0.3694(4) 0.0283(14) Uani 1 1 d . . . . .
C12 C 0.6481(4) 0.3684(4) 0.7420(4) 0.0305(14) Uani 1 1 d . . . . .
H12 H 0.692768 0.403325 0.754529 0.037 Uiso 1 1 calc R U . . .
C13 C 0.3225(4) 0.1425(3) 0.6770(4) 0.0253(13) Uani 1 1 d . . . . .
C14 C 0.6176(4) 0.3448(3) 0.6678(4) 0.0249(13) Uani 1 1 d . . . . .
H14 H 0.643330 0.362182 0.630543 0.030 Uiso 1 1 calc R U . . .
C15 C 0.6722(4) 0.0245(4) 0.5463(4) 0.0302(14) Uani 1 1 d . . . . .
H15 H 0.705343 -0.019654 0.543859 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5503(3) 0.2963(3) 0.6469(3) 0.0210(12) Uani 1 1 d . . . . .
C17 C 0.3396(4) 0.4469(4) 0.5421(4) 0.0298(14) Uani 1 1 d . . . . .
H17 H 0.302265 0.464469 0.568954 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3813(4) 0.1970(3) 0.7155(3) 0.0236(13) Uani 1 1 d . . . . .
C19 C 0.6535(4) 0.4081(4) 0.3109(4) 0.0375(16) Uani 1 1 d . . . . .
H19 H 0.706170 0.393887 0.307447 0.045 Uiso 1 1 calc R U . . .
C20 C 0.5439(4) 0.2916(4) 0.7788(3) 0.0289(14) Uani 1 1 d . . . . .
H20 H 0.519928 0.272542 0.816644 0.035 Uiso 1 1 calc R U . . .
C21 C 0.5566(4) 0.1017(3) 0.4929(3) 0.0259(13) Uani 1 1 d . . . . .
C22 C 0.6134(4) 0.3410(4) 0.7981(4) 0.0310(14) Uani 1 1 d . . . . .
H22 H 0.635996 0.355175 0.849022 0.037 Uiso 1 1 calc R U . . .
C23 C 0.4969(4) 0.4478(3) 0.3173(4) 0.0265(13) Uani 1 1 d . . . . .
H23 H 0.442719 0.459571 0.317498 0.032 Uiso 1 1 calc R U . . .
C24 C 0.4402(4) 0.2224(3) 0.6776(3) 0.0221(12) Uani 1 1 d . . . . .
C25 C 0.6090(4) 0.4578(4) 0.2608(4) 0.0378(17) Uani 1 1 d . . . . .
H25 H 0.631644 0.480332 0.223532 0.045 Uiso 1 1 calc R U . . .
C26 C 0.3564(4) 0.4940(4) 0.4859(4) 0.0283(14) Uani 1 1 d . . . . .
H26 H 0.330007 0.543139 0.473985 0.034 Uiso 1 1 calc R U . . .
C27 C 0.6351(4) 0.2943(4) 0.4683(4) 0.0272(13) Uani 1 1 d . . . . .
H27 H 0.665191 0.255197 0.500373 0.033 Uiso 1 1 calc R U . . .
C28 C 0.3758(4) 0.2238(4) 0.7866(4) 0.0272(14) Uani 1 1 d D . . . .
C29 C 0.3768(4) 0.3752(3) 0.5589(4) 0.0249(13) Uani 1 1 d . . . . .
H29 H 0.363404 0.343489 0.596551 0.030 Uiso 1 1 calc R U . . .
C30 C 0.4115(3) 0.4689(3) 0.4475(3) 0.0232(12) Uani 1 1 d . . . . .
H30 H 0.422980 0.500621 0.408980 0.028 Uiso 1 1 calc R U . . .
C31 C 0.6429(4) 0.1322(4) 0.6062(4) 0.0290(14) Uani 1 1 d . . . . .
H31 H 0.656117 0.166275 0.648462 0.035 Uiso 1 1 calc R U . . .
C32 C 0.3200(4) 0.1924(4) 0.8202(4) 0.0294(14) Uani 1 1 d . . . . .
H32 H 0.316662 0.210923 0.868071 0.035 Uiso 1 1 calc R U . . .
C33 C 0.5129(3) 0.2723(3) 0.7068(4) 0.0249(13) Uani 1 1 d . . . . .
H28 H 0.403(3) 0.269(2) 0.809(3) 0.024(17) Uiso 1 1 d D . . . .


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 O1 2.171(4) . ?
Ir1 N1 2.029(5) . ?
Ir1 N3 2.148(5) . ?
Ir1 N5 2.048(5) . ?
Ir1 C5 1.987(6) . ?
Ir1 C16 1.997(6) . ?
O1 C1 1.281(7) . ?
O2 C1 1.233(7) . ?
N1 C6 1.363(7) . ?
N1 C24 1.356(7) . ?
N2 C6 1.297(8) . ?
N2 C13 1.385(8) . ?
N3 C21 1.335(8) . ?
N3 C31 1.337(8) . ?
N4 C15 1.333(8) . ?
N4 C31 1.334(8) . ?
N5 C4 1.348(8) . ?
N5 C27 1.363(7) . ?
N6 C11 1.376(8) . ?
N6 C27 1.304(8) . ?
C1 C21 1.523(9) . ?
C2 H2 0.9500 . ?
C2 C8 1.348(10) . ?
C2 C13 1.407(8) . ?
C3 H3 0.9500 . ?
C3 C23 1.372(9) . ?
C3 C25 1.416(10) . ?
C4 C9 1.432(8) . ?
C4 C10 1.463(8) . ?
C5 C10 1.428(8) . ?
C5 C29 1.389(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C15 1.393(9) . ?
C7 C21 1.381(8) . ?
C8 H8 0.9500 . ?
C8 C32 1.410(9) . ?
C9 C11 1.410(8) . ?
C9 C23 1.415(9) . ?
C10 C30 1.399(8) . ?
C11 C19 1.426(9) . ?
C12 H12 0.9500 . ?
C12 C14 1.393(9) . ?
C12 C22 1.394(9) . ?
C13 C18 1.420(8) . ?
C14 H14 0.9500 . ?
C14 C16 1.390(8) . ?
C15 H15 0.9500 . ?
C16 C33 1.465(8) . ?
C17 H17 0.9500 . ?
C17 C26 1.394(9) . ?
C17 C29 1.375(8) . ?
C18 C24 1.430(8) . ?
C18 C28 1.411(8) . ?
C19 H19 0.9500 . ?
C19 C25 1.338(10) . ?
C20 H20 0.9500 . ?
C20 C22 1.427(9) . ?
C20 C33 1.336(9) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C33 1.490(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C30 1.381(8) . ?
C27 H27 0.9500 . ?
C28 C32 1.371(9) . ?
C28 H28 0.94(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 O1 93.95(17) . . ?
N1 Ir1 N3 93.37(19) . . ?
N1 Ir1 N5 172.25(19) . . ?
N3 Ir1 O1 76.24(18) . . ?
N5 Ir1 O1 84.70(17) . . ?
N5 Ir1 N3 93.71(19) . . ?
C5 Ir1 O1 97.73(19) . . ?
C5 Ir1 N1 93.0(2) . . ?
C5 Ir1 N3 171.5(2) . . ?
C5 Ir1 N5 79.6(2) . . ?
C5 Ir1 C16 88.1(2) . . ?
C16 Ir1 O1 171.60(19) . . ?
C16 Ir1 N1 79.7(2) . . ?
C16 Ir1 N3 98.5(2) . . ?
C16 Ir1 N5 102.3(2) . . ?
C1 O1 Ir1 117.1(4) . . ?
C6 N1 Ir1 121.4(4) . . ?
C24 N1 Ir1 118.5(4) . . ?
C24 N1 C6 119.8(5) . . ?
C6 N2 C13 116.0(5) . . ?
C21 N3 Ir1 114.6(4) . . ?
C21 N3 C31 117.9(5) . . ?
C31 N3 Ir1 127.2(4) . . ?
C15 N4 C31 115.8(6) . . ?
C4 N5 Ir1 115.0(4) . . ?
C4 N5 C27 118.0(5) . . ?
C27 N5 Ir1 126.6(4) . . ?
C27 N6 C11 115.1(5) . . ?
O1 C1 C21 114.8(5) . . ?
O2 C1 O1 126.6(6) . . ?
O2 C1 C21 118.6(5) . . ?
C8 C2 H2 119.8 . . ?
C8 C2 C13 120.3(6) . . ?
C13 C2 H2 119.8 . . ?
C23 C3 H3 120.3 . . ?
C23 C3 C25 119.4(6) . . ?
C25 C3 H3 120.3 . . ?
N5 C4 C9 119.0(5) . . ?
N5 C4 C10 112.9(5) . . ?
C9 C4 C10 128.0(5) . . ?
C10 C5 Ir1 114.4(4) . . ?
C29 C5 Ir1 128.4(5) . . ?
C29 C5 C10 116.9(5) . . ?
N1 C6 H6 116.9 . . ?
N2 C6 N1 126.3(6) . . ?
N2 C6 H6 116.9 . . ?
C15 C7 H7 121.3 . . ?
C21 C7 H7 121.3 . . ?
C21 C7 C15 117.4(6) . . ?
C2 C8 H8 119.7 . . ?
C2 C8 C32 120.7(6) . . ?
C32 C8 H8 119.7 . . ?
C11 C9 C4 116.4(6) . . ?
C11 C9 C23 119.2(6) . . ?
C23 C9 C4 124.4(6) . . ?
C5 C10 C4 114.1(5) . . ?
C30 C10 C4 124.3(5) . . ?
C30 C10 C5 121.0(5) . . ?
N6 C11 C9 122.7(6) . . ?
N6 C11 C19 118.1(6) . . ?
C9 C11 C19 119.1(6) . . ?
C14 C12 H12 119.8 . . ?
C14 C12 C22 120.3(6) . . ?
C22 C12 H12 119.8 . . ?
N2 C13 C2 118.0(6) . . ?
N2 C13 C18 122.1(5) . . ?
C2 C13 C18 119.8(6) . . ?
C12 C14 H14 119.3 . . ?
C16 C14 C12 121.4(6) . . ?
C16 C14 H14 119.3 . . ?
N4 C15 C7 122.4(6) . . ?
N4 C15 H15 118.8 . . ?
C7 C15 H15 118.8 . . ?
C14 C16 Ir1 127.2(5) . . ?
C14 C16 C33 116.6(5) . . ?
C33 C16 Ir1 116.2(4) . . ?
C26 C17 H17 119.8 . . ?
C29 C17 H17 119.8 . . ?
C29 C17 C26 120.4(6) . . ?
C13 C18 C24 116.9(5) . . ?
C28 C18 C13 117.9(6) . . ?
C28 C18 C24 125.1(6) . . ?
C11 C19 H19 120.0 . . ?
C25 C19 C11 119.9(7) . . ?
C25 C19 H19 120.0 . . ?
C22 C20 H20 120.4 . . ?
C33 C20 H20 120.4 . . ?
C33 C20 C22 119.2(6) . . ?
N3 C21 C1 116.7(5) . . ?
N3 C21 C7 120.5(6) . . ?
C7 C21 C1 122.8(6) . . ?
C12 C22 C20 119.8(6) . . ?
C12 C22 H22 120.1 . . ?
C20 C22 H22 120.1 . . ?
C3 C23 C9 120.2(6) . . ?
C3 C23 H23 119.9 . . ?
C9 C23 H23 119.9 . . ?
N1 C24 C18 118.1(5) . . ?
N1 C24 C33 113.4(5) . . ?
C18 C24 C33 128.5(6) . . ?
C3 C25 H25 119.1 . . ?
C19 C25 C3 121.8(6) . . ?
C19 C25 H25 119.1 . . ?
C17 C26 H26 120.1 . . ?
C30 C26 C17 119.8(6) . . ?
C30 C26 H26 120.1 . . ?
N5 C27 H27 116.2 . . ?
N6 C27 N5 127.6(6) . . ?
N6 C27 H27 116.2 . . ?
C18 C28 H28 122(4) . . ?
C32 C28 C18 120.6(6) . . ?
C32 C28 H28 117(4) . . ?
C5 C29 H29 119.0 . . ?
C17 C29 C5 122.1(6) . . ?
C17 C29 H29 119.0 . . ?
C10 C30 H30 120.1 . . ?
C26 C30 C10 119.7(6) . . ?
C26 C30 H30 120.1 . . ?
N3 C31 H31 117.0 . . ?
N4 C31 N3 125.9(6) . . ?
N4 C31 H31 117.0 . . ?
C8 C32 H32 120.0 . . ?
C28 C32 C8 120.1(6) . . ?
C28 C32 H32 120.0 . . ?
C16 C33 C24 111.7(5) . . ?
C20 C33 C16 122.5(6) . . ?
C20 C33 C24 125.7(6) . . ?

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
Ir1 O1 C1 O2 175.1(5) . . . . ?
Ir1 O1 C1 C21 -5.1(6) . . . . ?
Ir1 N1 C6 N2 -177.7(5) . . . . ?
Ir1 N1 C24 C18 170.0(4) . . . . ?
Ir1 N1 C24 C33 -8.0(7) . . . . ?
Ir1 N3 C21 C1 -6.7(7) . . . . ?
Ir1 N3 C21 C7 174.1(5) . . . . ?
Ir1 N3 C31 N4 -173.5(5) . . . . ?
Ir1 N5 C4 C9 -162.3(4) . . . . ?
Ir1 N5 C4 C10 21.1(6) . . . . ?
Ir1 N5 C27 N6 169.9(5) . . . . ?
Ir1 C5 C10 C4 -3.2(6) . . . . ?
Ir1 C5 C10 C30 -175.3(4) . . . . ?
Ir1 C5 C29 C17 173.4(5) . . . . ?
Ir1 C16 C33 C20 173.5(5) . . . . ?
Ir1 C16 C33 C24 -4.1(6) . . . . ?
O1 C1 C21 N3 8.0(8) . . . . ?
O1 C1 C21 C7 -172.8(6) . . . . ?
O2 C1 C21 N3 -172.2(6) . . . . ?
O2 C1 C21 C7 7.0(9) . . . . ?
N1 C24 C33 C16 7.6(7) . . . . ?
N1 C24 C33 C20 -169.9(6) . . . . ?
N2 C13 C18 C24 -7.8(9) . . . . ?
N2 C13 C18 C28 170.3(6) . . . . ?
N5 C4 C9 C11 -11.2(8) . . . . ?
N5 C4 C9 C23 166.9(6) . . . . ?
N5 C4 C10 C5 -11.8(7) . . . . ?
N5 C4 C10 C30 160.1(6) . . . . ?
N6 C11 C19 C25 179.3(7) . . . . ?
C2 C8 C32 C28 -4.3(10) . . . . ?
C2 C13 C18 C24 173.6(6) . . . . ?
C2 C13 C18 C28 -8.3(9) . . . . ?
C4 N5 C27 N6 -2.7(10) . . . . ?
C4 C9 C11 N6 3.2(9) . . . . ?
C4 C9 C11 C19 -176.3(6) . . . . ?
C4 C9 C23 C3 176.0(6) . . . . ?
C4 C10 C30 C26 -170.6(6) . . . . ?
C5 C10 C30 C26 0.7(9) . . . . ?
C6 N1 C24 C18 -3.5(8) . . . . ?
C6 N1 C24 C33 178.5(5) . . . . ?
C6 N2 C13 C2 179.3(6) . . . . ?
C6 N2 C13 C18 0.6(9) . . . . ?
C8 C2 C13 N2 -174.2(6) . . . . ?
C8 C2 C13 C18 4.5(10) . . . . ?
C9 C4 C10 C5 172.0(6) . . . . ?
C9 C4 C10 C30 -16.2(10) . . . . ?
C9 C11 C19 C25 -1.2(10) . . . . ?
C10 C4 C9 C11 164.8(6) . . . . ?
C10 C4 C9 C23 -17.1(10) . . . . ?
C10 C5 C29 C17 -1.2(9) . . . . ?
C11 N6 C27 N5 -5.3(10) . . . . ?
C11 C9 C23 C3 -5.9(9) . . . . ?
C11 C19 C25 C3 -2.9(11) . . . . ?
C12 C14 C16 Ir1 -176.4(5) . . . . ?
C12 C14 C16 C33 0.7(8) . . . . ?
C13 N2 C6 N1 5.9(10) . . . . ?
C13 C2 C8 C32 1.9(11) . . . . ?
C13 C18 C24 N1 9.0(8) . . . . ?
C13 C18 C24 C33 -173.4(6) . . . . ?
C13 C18 C28 C32 6.0(9) . . . . ?
C14 C12 C22 C20 -3.0(10) . . . . ?
C14 C16 C33 C20 -4.0(8) . . . . ?
C14 C16 C33 C24 178.5(5) . . . . ?
C15 N4 C31 N3 -0.5(10) . . . . ?
C15 C7 C21 N3 0.8(9) . . . . ?
C15 C7 C21 C1 -178.4(6) . . . . ?
C17 C26 C30 C10 -0.3(9) . . . . ?
C18 C24 C33 C16 -170.2(6) . . . . ?
C18 C24 C33 C20 12.4(10) . . . . ?
C18 C28 C32 C8 0.2(9) . . . . ?
C21 N3 C31 N4 0.5(10) . . . . ?
C21 C7 C15 N4 -0.8(10) . . . . ?
C22 C12 C14 C16 2.7(10) . . . . ?
C22 C20 C33 C16 3.6(9) . . . . ?
C22 C20 C33 C24 -179.1(6) . . . . ?
C23 C3 C25 C19 2.6(11) . . . . ?
C23 C9 C11 N6 -175.0(6) . . . . ?
C23 C9 C11 C19 5.5(9) . . . . ?
C24 N1 C6 N2 -4.4(10) . . . . ?
C24 C18 C28 C32 -176.1(6) . . . . ?
C25 C3 C23 C9 1.9(10) . . . . ?
C26 C17 C29 C5 1.6(10) . . . . ?
C27 N5 C4 C9 11.1(8) . . . . ?
C27 N5 C4 C10 -165.5(5) . . . . ?
C27 N6 C11 C9 4.7(9) . . . . ?
C27 N6 C11 C19 -175.8(6) . . . . ?
C28 C18 C24 N1 -169.0(6) . . . . ?
C28 C18 C24 C33 8.7(10) . . . . ?
C29 C5 C10 C4 172.1(5) . . . . ?
C29 C5 C10 C30 0.0(8) . . . . ?
C29 C17 C26 C30 -0.9(10) . . . . ?
C31 N3 C21 C1 178.7(5) . . . . ?
C31 N3 C21 C7 -0.6(9) . . . . ?
C31 N4 C15 C7 0.7(10) . . . . ?
C33 C20 C22 C12 -0.1(10) . . . . ?

