# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1_21srv206
_database_code_depnum_ccdc_archive 'CCDC 2288521'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_audit_creation_date             2021-04-20
_audit_creation_method           
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C64 H50 Ir2 N6 O2'
_chemical_formula_sum            'C64 H50 Ir2 N6 O2'
_chemical_formula_weight         1319.50
_chemical_melting_point          ?
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'

_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.
;
_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'
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                   30.2193(13)
_cell_length_b                   12.6557(5)
_cell_length_c                   14.4652(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.1202(14)
_cell_angle_gamma                90
_cell_volume                     5008.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7507
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.794
_exptl_absorpt_coefficient_mu    5.362
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0828 before and 0.0766 after correction.
The Ratio of minimum to maximum transmission is 0.8937.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2584
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.006
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            52134
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.140
_diffrn_ambient_temperature      130.0
_diffrn_detector                 'Bruker PHOTON III C14 MM CPAD'
_diffrn_detector_area_resol_mean 54.4
_diffrn_detector_type            'CPA sensor'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0 microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    ?
_reflns_Friedel_fraction_max     ?
_reflns_number_gt                4254
_reflns_number_total             6047
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         1.001
_refine_diff_density_min         -1.475
_refine_diff_density_rms         0.207
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6047
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0181P)²+38.5165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C29(H29), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.39592(2) 0.35620(2) 0.58357(2) 0.01473(7) Uani 1 1 d . . . . .
O1 O 0.39062(15) 0.4893(3) 0.4872(3) 0.0182(9) Uani 1 1 d . . . . .
N1 N 0.45784(16) 0.4475(4) 0.6902(4) 0.0153(11) Uani 1 1 d . . . . .
N2 N 0.34396(17) 0.4204(4) 0.6219(4) 0.0162(11) Uani 1 1 d . . . . .
N3 N 0.44390(17) 0.2822(4) 0.5416(4) 0.0178(11) Uani 1 1 d . . . . .
C1 C 0.500000 0.4000(7) 0.750000 0.0167(18) Uani 1 2 d S T P . .
H1 H 0.500000 0.324957 0.750001 0.020 Uiso 1 2 calc R U P . .
C2 C 0.4574(2) 0.5546(5) 0.6893(4) 0.0181(13) Uani 1 1 d . . . . .
C3 C 0.500000 0.6075(7) 0.750000 0.0172(19) Uani 1 2 d S T P . .
H3 H 0.500000 0.682536 0.750002 0.021 Uiso 1 2 calc R U P . .
C4 C 0.4142(2) 0.6157(5) 0.6226(5) 0.0177(14) Uani 1 1 d . . . . .
C5 C 0.3837(2) 0.5797(5) 0.5236(5) 0.0163(13) Uani 1 1 d . . . . .
C6 C 0.3456(2) 0.6465(5) 0.4602(5) 0.0238(13) Uani 1 1 d . . . . .
H6 H 0.325532 0.625357 0.392145 0.029 Uiso 1 1 calc R U . . .
C7 C 0.3368(2) 0.7415(5) 0.4950(5) 0.0279(16) Uani 1 1 d . . . . .
H7 H 0.309774 0.783380 0.452204 0.033 Uiso 1 1 calc R U . . .
C8 C 0.3675(2) 0.7773(5) 0.5930(5) 0.0222(14) Uani 1 1 d . . . . .
H8 H 0.362079 0.844375 0.615880 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4054(2) 0.7150(5) 0.6558(5) 0.0240(15) Uani 1 1 d . . . . .
H9 H 0.426045 0.738997 0.722595 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3521(2) 0.4730(5) 0.7082(5) 0.0194(14) Uani 1 1 d . . . . .
H10 H 0.384496 0.476136 0.760298 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3158(2) 0.5224(5) 0.7246(5) 0.0228(15) Uani 1 1 d . . . . .
H11 H 0.323102 0.560028 0.786188 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2676(3) 0.5168(6) 0.6493(5) 0.0290(17) Uani 1 1 d . . . . .
H12 H 0.241816 0.551562 0.658228 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2585(2) 0.4597(5) 0.5620(5) 0.0245(15) Uani 1 1 d . . . . .
H13 H 0.226018 0.453615 0.510809 0.029 Uiso 1 1 calc R U . . .
C14 C 0.2963(2) 0.4111(5) 0.5482(5) 0.0173(13) Uani 1 1 d . . . . .
C15 C 0.2922(2) 0.3438(5) 0.4635(4) 0.0167(13) Uani 1 1 d . . . . .
C16 C 0.3356(2) 0.3001(5) 0.4677(4) 0.0160(13) Uani 1 1 d . . . . .
C17 C 0.3330(2) 0.2351(5) 0.3873(5) 0.0208(14) Uani 1 1 d . . . . .
H17 H 0.362122 0.202970 0.390794 0.025 Uiso 1 1 calc R U . . .
C18 C 0.2895(2) 0.2160(5) 0.3028(5) 0.0216(14) Uani 1 1 d . . . . .
C19 C 0.2466(2) 0.2620(5) 0.2995(5) 0.0210(14) Uani 1 1 d . . . . .
H19 H 0.216387 0.249921 0.242208 0.025 Uiso 1 1 calc R U . . .
C20 C 0.2479(2) 0.3246(5) 0.3784(5) 0.0206(14) Uani 1 1 d . . . . .
H20 H 0.218580 0.354942 0.375225 0.025 Uiso 1 1 calc R U . . .
C21 C 0.2878(2) 0.1518(6) 0.2145(5) 0.0305(16) Uani 1 1 d . . . . .
H21A H 0.320987 0.129513 0.227369 0.046 Uiso 1 1 calc R U . . .
H21B H 0.274070 0.194533 0.152176 0.046 Uiso 1 1 calc R U . . .
H21C H 0.267323 0.089327 0.206230 0.046 Uiso 1 1 calc R U . . .
C22 C 0.4660(2) 0.3288(5) 0.4891(5) 0.0229(15) Uani 1 1 d . . . . .
H22 H 0.457972 0.399659 0.466702 0.027 Uiso 1 1 calc R U . . .
C23 C 0.5002(2) 0.2757(6) 0.4670(5) 0.0249(15) Uani 1 1 d . . . . .
H23 H 0.516822 0.310739 0.432812 0.030 Uiso 1 1 calc R U . . .
C24 C 0.5100(3) 0.1718(6) 0.4949(6) 0.0337(18) Uani 1 1 d . . . . .
H24 H 0.531864 0.132886 0.476269 0.040 Uiso 1 1 calc R U . . .
C25 C 0.4882(2) 0.1246(5) 0.5499(5) 0.0260(16) Uani 1 1 d . . . . .
H25 H 0.495734 0.053260 0.571318 0.031 Uiso 1 1 calc R U . . .
C26 C 0.4549(2) 0.1803(5) 0.5745(5) 0.0190(14) Uani 1 1 d . . . . .
C27 C 0.4319(2) 0.1436(6) 0.6388(4) 0.0175(12) Uani 1 1 d . . . . .
C28 C 0.4041(2) 0.2218(5) 0.6615(4) 0.0176(13) Uani 1 1 d . . . . .
C29 C 0.3852(2) 0.1935(5) 0.7311(5) 0.0196(14) Uani 1 1 d . . . . .
H29 H 0.367182 0.244706 0.748929 0.024 Uiso 1 1 calc R U . . .
C30 C 0.3916(2) 0.0928(5) 0.7758(5) 0.0220(15) Uani 1 1 d . . . . .
C31 C 0.4169(2) 0.0178(5) 0.7461(5) 0.0241(15) Uani 1 1 d . . . . .
H31 H 0.420187 -0.051966 0.772388 0.029 Uiso 1 1 calc R U . . .
C32 C 0.4373(2) 0.0422(5) 0.6800(5) 0.0246(15) Uani 1 1 d . . . . .
H32 H 0.455022 -0.009862 0.662371 0.030 Uiso 1 1 calc R U . . .
C33 C 0.3714(3) 0.0670(6) 0.8512(5) 0.0299(16) Uani 1 1 d . . . . .
H33A H 0.377610 0.125900 0.899115 0.045 Uiso 1 1 calc R U . . .
H33B H 0.387181 0.002985 0.888967 0.045 Uiso 1 1 calc R U . . .
H33C H 0.336080 0.055097 0.815043 0.045 Uiso 1 1 calc R U . . .


_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_
_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 2.149(4) . ?
Ir1 N1 2.183(4) . ?
Ir1 N2 2.043(5) . ?
Ir1 N3 2.023(5) . ?
Ir1 C16 2.011(6) . ?
Ir1 C28 1.997(6) . ?
O1 C5 1.313(7) . ?
N1 C1 1.341(6) . ?
N1 C2 1.355(7) . ?
N2 C10 1.343(7) . ?
N2 C14 1.386(7) . ?
N3 C22 1.343(8) . ?
N3 C26 1.366(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(7) . ?
C2 C4 1.471(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(8) . ?
C4 C9 1.410(9) . ?
C5 C6 1.409(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.371(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.400(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.369(8) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.368(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.401(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(8) . ?
C14 C15 1.453(8) . ?
C15 C16 1.400(8) . ?
C15 C20 1.402(8) . ?
C16 C17 1.401(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(8) . ?
C18 C19 1.403(9) . ?
C18 C21 1.496(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.375(9) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.379(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.370(9) . ?
C24 H24 0.9500 . ?
C24 C25 1.368(9) . ?
C25 H25 0.9500 . ?
C25 C26 1.394(8) . ?
C26 C27 1.453(8) . ?
C27 C28 1.425(8) . ?
C27 C32 1.394(9) . ?
C28 C29 1.398(9) . ?
C29 H29 0.9500 . ?
C29 C30 1.405(8) . ?
C30 C31 1.396(9) . ?
C30 C33 1.496(9) . ?
C31 H31 0.9500 . ?
C31 C32 1.375(9) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

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
O1 Ir1 N1 81.31(17) . . ?
N2 Ir1 O1 90.61(18) . . ?
N2 Ir1 N1 97.17(19) . . ?
N3 Ir1 O1 91.93(18) . . ?
N3 Ir1 N1 87.04(19) . . ?
N3 Ir1 N2 175.4(2) . . ?
C16 Ir1 O1 86.8(2) . . ?
C16 Ir1 N1 167.9(2) . . ?
C16 Ir1 N2 80.6(2) . . ?
C16 Ir1 N3 95.7(2) . . ?
C28 Ir1 O1 172.4(2) . . ?
C28 Ir1 N1 100.9(2) . . ?
C28 Ir1 N2 96.3(2) . . ?
C28 Ir1 N3 80.9(2) . . ?
C28 Ir1 C16 91.2(2) . . ?
C5 O1 Ir1 113.8(4) . . ?
C1 N1 Ir1 120.9(4) . . ?
C1 N1 C2 117.2(5) . . ?
C2 N1 Ir1 121.4(4) . . ?
C10 N2 Ir1 126.3(4) . . ?
C10 N2 C14 118.5(5) . . ?
C14 N2 Ir1 115.1(4) . . ?
C22 N3 Ir1 124.0(4) . . ?
C22 N3 C26 120.3(5) . . ?
C26 N3 Ir1 115.6(4) . . ?
N1 C1 N1 126.7(8) . 2_656 ?
N1 C1 H1 116.6 . . ?
N1 C1 H1 116.6 2_656 . ?
N1 C2 C3 118.3(6) . . ?
N1 C2 C4 122.3(5) . . ?
C3 C2 C4 119.3(6) . . ?
C2 C3 C2 122.2(8) 2_656 . ?
C2 C3 H3 118.9 . . ?
C2 C3 H3 118.9 2_656 . ?
C5 C4 C2 120.8(5) . . ?
C9 C4 C2 119.3(5) . . ?
C9 C4 C5 119.8(5) . . ?
O1 C5 C4 122.8(5) . . ?
O1 C5 C6 119.2(5) . . ?
C6 C5 C4 117.9(5) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.3(6) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.5(6) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(6) . . ?
C9 C8 H8 120.2 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.9(6) . . ?
C8 C9 H9 119.6 . . ?
N2 C10 H10 118.5 . . ?
N2 C10 C11 123.0(6) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.2(6) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.4(6) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.7(6) . . ?
C14 C13 H13 119.6 . . ?
N2 C14 C15 112.8(5) . . ?
C13 C14 N2 120.1(6) . . ?
C13 C14 C15 127.0(6) . . ?
C16 C15 C14 116.8(5) . . ?
C16 C15 C20 119.7(6) . . ?
C20 C15 C14 123.4(5) . . ?
C15 C16 Ir1 113.5(4) . . ?
C15 C16 C17 118.4(5) . . ?
C17 C16 Ir1 127.6(5) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.1(6) . . ?
C18 C17 H17 118.9 . . ?
C17 C18 C19 118.4(6) . . ?
C17 C18 C21 121.5(6) . . ?
C19 C18 C21 120.0(6) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(6) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.6(6) . . ?
C19 C20 H20 119.7 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 H22 119.3 . . ?
N3 C22 C23 121.3(6) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.2(6) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.6(7) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.4(6) . . ?
C26 C25 H25 119.8 . . ?
N3 C26 C25 119.0(6) . . ?
N3 C26 C27 114.4(5) . . ?
C25 C26 C27 126.5(6) . . ?
C28 C27 C26 114.5(6) . . ?
C32 C27 C26 124.6(6) . . ?
C32 C27 C28 120.9(6) . . ?
C27 C28 Ir1 113.9(4) . . ?
C29 C28 Ir1 129.4(5) . . ?
C29 C28 C27 116.7(6) . . ?
C28 C29 H29 118.5 . . ?
C28 C29 C30 123.1(6) . . ?
C30 C29 H29 118.5 . . ?
C29 C30 C33 121.0(6) . . ?
C31 C30 C29 117.5(6) . . ?
C31 C30 C33 121.5(6) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 C30 121.8(6) . . ?
C32 C31 H31 119.1 . . ?
C27 C32 H32 120.0 . . ?
C31 C32 C27 119.9(6) . . ?
C31 C32 H32 120.0 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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
C3 C2 C4 C5 140.8(5) . . . . ?
C3 C2 C4 C9 -34.6(8) . . . . ?
C4 C5 O1 Ir1 53.1(7) . . . . ?
C5 C4 C2 N1 -36.0(9) . . . . ?
C6 C5 O1 Ir1 -129.8(5) . . . . ?
C9 C4 C2 N1 148.6(6) . . . . ?
C13 C14 C15 C16 -177.7(6) . . . . ?
C13 C14 C15 C20 4.5(10) . . . . ?
C16 C15 C14 N2 -0.6(8) . . . . ?
C20 C15 C14 N2 -178.3(6) . . . . ?
C25 C26 C27 C28 172.5(6) . . . . ?
C25 C26 C27 C32 -4.9(10) . . . . ?
C28 C27 C26 N3 -3.5(7) . . . . ?
C32 C27 C26 N3 179.2(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
