# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_NBU_BN_05_JR
_database_code_depnum_ccdc_archive 'CCDC 2446414'
loop_
_audit_author_name
_audit_author_address
'Rajesh K Das'
;Department of Chemistry University of North Bengal
India
;
_audit_update_record             
;
2025-04-24 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_iupac          ?
_chemical_formula_moiety         'C24 H28 Cl F Ir N3 O'
_chemical_formula_sum            'C24 H28 Cl F Ir N3 O'
_chemical_formula_weight         621.14
_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'
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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   17.2778(15)
_cell_length_b                   7.6362(7)
_cell_length_c                   17.0623(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.242(2)
_cell_angle_gamma                90
_cell_volume                     2245.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9309
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      26.4122
_cell_measurement_theta_min      2.7474
_exptl_absorpt_coefficient_mu    6.096
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.362
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.262
_exptl_special_details           
;
;
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            82895
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_min         2.75
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           ?
_diffrn_source_power             ?
_diffrn_source_type              ?
_diffrn_source_voltage           ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4308
_reflns_number_total             4621
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_refine_diff_density_max         1.738
_refine_diff_density_min         -0.740
_refine_ls_extinction_coef       0.00247(16)
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    ?
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0193
_refine_ls_restrained_S_all      1.083
_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)+(0.0196P)²+4.0283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0452
_refine_ls_wR_factor_ref         0.0476
_refine_special_details          
;
;
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C14(H14), C15(H15), C17(H17), C18(H18)
1.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir1 0.80784(2) 0.54513(2) 0.49155(2) 0.01746(6) Uani d . . . 1 . .
Cl Cl1 0.90136(4) 0.33998(10) 0.44526(4) 0.02513(15) Uani d . . . 1 . .
F F2 1.01347(12) 0.5149(3) 0.74545(12) 0.0435(5) Uani d . . . 1 . .
O O2 0.69122(13) 0.1990(3) 0.62947(13) 0.0339(5) Uani d . . . 1 . .
N N2 0.85300(14) 0.4706(3) 0.60325(14) 0.0191(5) Uani d . . . 1 . .
N N3 0.73596(13) 0.3360(3) 0.51987(14) 0.0197(5) Uani d . . . 1 . .
N N4 0.53195(16) 0.0222(4) 0.28709(17) 0.0331(6) Uani d . . . 1 . .
C C1 0.6399(2) 0.6440(5) 0.3962(3) 0.0453(10) Uani d . . . 1 . .
H H1A 0.612007 0.743874 0.371533 0.068000 Uiso calc U . R 1 . .
H H1B 0.611116 0.599018 0.439242 0.068000 Uiso calc U . R 1 . .
H H1C 0.644853 0.551556 0.357002 0.068000 Uiso calc U . R 1 . .
C C2 0.81794(18) 0.8257(4) 0.50832(18) 0.0253(6) Uani d . . . 1 . .
C C3 0.78757(19) 0.7016(4) 0.38598(18) 0.0279(7) Uani d . . . 1 . .
C C4 0.92180(17) 0.5193(4) 0.63745(18) 0.0246(6) Uani d . . . 1 . .
H H4 0.955603 0.590755 0.609762 0.030000 Uiso calc U . R 1 . .
C C5 0.94345(18) 0.4656(4) 0.71299(19) 0.0270(7) Uani d . . . 1 . .
C C6 0.89636(19) 0.3626(4) 0.75545(18) 0.0282(7) Uani d . . . 1 . .
H H6 0.911364 0.328044 0.807872 0.034000 Uiso calc U . R 1 . .
C C7 0.82625(18) 0.3117(4) 0.71826(17) 0.0259(6) Uani d . . . 1 . .
H H7 0.791776 0.240032 0.744999 0.031000 Uiso calc U . R 1 . .
C C8 0.80647(16) 0.3649(4) 0.64251(16) 0.0201(6) Uani d . . . 1 . .
C C9 0.73747(18) 0.7712(4) 0.50498(19) 0.0268(6) Uani d . . . 1 . .
C C10 0.84948(18) 0.7810(4) 0.43628(18) 0.0258(6) Uani d . . . 1 . .
C C11 0.71903(18) 0.7015(4) 0.4277(2) 0.0291(7) Uani d . . . 1 . .
C C12 0.73681(16) 0.2944(4) 0.59629(17) 0.0221(6) Uani d . . . 1 . .
C C13 0.68256(16) 0.2542(4) 0.46408(17) 0.0206(6) Uani d . . . 1 . .
C C14 0.70826(17) 0.2058(4) 0.39169(18) 0.0274(7) Uani d . . . 1 . .
H H14 0.760919 0.226069 0.381842 0.033000 Uiso calc U . R 1 . .
C C15 0.65941(17) 0.1291(5) 0.33386(19) 0.0291(7) Uani d . . . 1 . .
H H15 0.678980 0.098216 0.285139 0.035000 Uiso calc U . R 1 . .
C C16 0.58153(17) 0.0963(4) 0.34590(18) 0.0251(6) Uani d . . . 1 . .
C C17 0.55600(17) 0.1429(4) 0.41904(18) 0.0266(6) Uani d . . . 1 . .
H H17 0.503665 0.120509 0.429482 0.032000 Uiso calc U . R 1 . .
C C18 0.60531(17) 0.2211(4) 0.47659(18) 0.0258(6) Uani d . . . 1 . .
H H18 0.585995 0.252487 0.525363 0.031000 Uiso calc U . R 1 . .
C C19 0.6820(2) 0.7982(5) 0.5666(2) 0.0439(9) Uani d . . . 1 . .
H H19A 0.657311 0.913267 0.559529 0.066000 Uiso calc U . R 1 . .
H H19B 0.709945 0.792437 0.618677 0.066000 Uiso calc U . R 1 . .
H H19C 0.642099 0.706710 0.562302 0.066000 Uiso calc U . R 1 . .
C C20 0.8610(2) 0.9195(5) 0.5745(2) 0.0385(8) Uani d . . . 1 . .
H H20A 0.859683 1.045719 0.564152 0.058000 Uiso calc U . R 1 . .
H H20B 0.914988 0.879185 0.579386 0.058000 Uiso calc U . R 1 . .
H H20C 0.836659 0.895199 0.623407 0.058000 Uiso calc U . R 1 . .
C C21 0.9303(2) 0.8171(5) 0.4153(2) 0.0392(9) Uani d . . . 1 . .
H H21A 0.936891 0.943329 0.407825 0.059000 Uiso calc U . R 1 . .
H H21B 0.939746 0.755536 0.366503 0.059000 Uiso calc U . R 1 . .
H H21C 0.967209 0.776191 0.457682 0.059000 Uiso calc U . R 1 . .
C C22 0.7937(3) 0.6458(5) 0.30289(19) 0.0453(9) Uani d . . . 1 . .
H H22A 0.791992 0.749246 0.268785 0.068000 Uiso calc U . R 1 . .
H H22B 0.750320 0.567984 0.286766 0.068000 Uiso calc U . R 1 . .
H H22C 0.842814 0.583676 0.298520 0.068000 Uiso calc U . R 1 . .
C C23 0.5629(2) -0.0387(5) 0.2159(2) 0.0361(8) Uani d . . . 1 . .
H H23A 0.520469 -0.080321 0.179362 0.054000 Uiso calc U . R 1 . .
H H23B 0.599432 -0.134732 0.228237 0.054000 Uiso calc U . R 1 . .
H H23C 0.590022 0.057678 0.191594 0.054000 Uiso calc U . R 1 . .
C C24 0.45839(19) -0.0470(5) 0.3068(2) 0.0347(8) Uani d . . . 1 . .
H H24A 0.433688 -0.109180 0.261321 0.052000 Uiso calc U . R 1 . .
H H24B 0.424820 0.049290 0.321378 0.052000 Uiso calc U . R 1 . .
H H24C 0.466556 -0.128256 0.351091 0.052000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 Cl1 . 2.4244(7) ?
Ir1 N2 . 2.084(2) ?
Ir1 N3 . 2.101(2) ?
Ir1 C2 . 2.167(3) ?
Ir1 C3 . 2.168(3) ?
Ir1 C9 . 2.133(3) ?
Ir1 C10 . 2.180(3) ?
Ir1 C11 . 2.172(3) ?
F2 C5 . 1.346(4) ?
O2 C12 . 1.240(4) ?
N2 C4 . 1.338(4) ?
N2 C8 . 1.351(4) ?
N3 C12 . 1.341(4) ?
N3 C13 . 1.420(4) ?
N4 C16 . 1.391(4) ?
N4 C23 . 1.440(5) ?
N4 C24 . 1.439(4) ?
C1 H1A . 0.980000 ?
C1 H1B . 0.980000 ?
C1 H1C . 0.980000 ?
C1 C11 . 1.498(4) ?
C2 C9 . 1.449(4) ?
C2 C10 . 1.423(4) ?
C2 C20 . 1.488(5) ?
C3 C10 . 1.453(4) ?
C3 C11 . 1.426(5) ?
C3 C22 . 1.492(5) ?
C4 H4 . 0.950000 ?
C4 C5 . 1.378(4) ?
C5 C6 . 1.376(5) ?
C6 H6 . 0.950000 ?
C6 C7 . 1.381(4) ?
C7 H7 . 0.950000 ?
C7 C8 . 1.374(4) ?
C8 C12 . 1.490(4) ?
C9 C11 . 1.435(5) ?
C9 C19 . 1.490(5) ?
C10 C21 . 1.492(4) ?
C13 C14 . 1.393(4) ?
C13 C18 . 1.390(4) ?
C14 H14 . 0.950000 ?
C14 C15 . 1.380(4) ?
C15 H15 . 0.950000 ?
C15 C16 . 1.399(4) ?
C16 C17 . 1.400(4) ?
C17 H17 . 0.950000 ?
C17 C18 . 1.386(4) ?
C18 H18 . 0.950000 ?
C19 H19A . 0.980000 ?
C19 H19B . 0.980000 ?
C19 H19C . 0.980000 ?
C20 H20A . 0.980000 ?
C20 H20B . 0.980000 ?
C20 H20C . 0.980000 ?
C21 H21A . 0.980000 ?
C21 H21B . 0.980000 ?
C21 H21C . 0.980000 ?
C22 H22A . 0.980000 ?
C22 H22B . 0.980000 ?
C22 H22C . 0.980000 ?
C23 H23A . 0.980000 ?
C23 H23B . 0.980000 ?
C23 H23C . 0.980000 ?
C24 H24A . 0.980000 ?
C24 H24B . 0.980000 ?
C24 H24C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 Ir1 Cl1 . . 84.72(7) ?
N2 Ir1 N3 . . 76.69(9) ?
N2 Ir1 C2 . . 97.37(11) ?
N2 Ir1 C3 . . 159.49(11) ?
N2 Ir1 C9 . . 107.49(11) ?
N2 Ir1 C10 . . 120.54(11) ?
N2 Ir1 C11 . . 144.21(11) ?
N3 Ir1 Cl1 . . 90.19(7) ?
N3 Ir1 C2 . . 139.85(10) ?
N3 Ir1 C3 . . 123.22(11) ?
N3 Ir1 C9 . . 103.83(11) ?
N3 Ir1 C10 . . 161.29(11) ?
N3 Ir1 C11 . . 97.21(11) ?
C2 Ir1 Cl1 . . 129.26(8) ?
C2 Ir1 C3 . . 64.62(12) ?
C2 Ir1 C10 . . 38.21(11) ?
C2 Ir1 C11 . . 64.51(12) ?
C3 Ir1 Cl1 . . 98.98(9) ?
C3 Ir1 C10 . . 39.06(12) ?
C3 Ir1 C11 . . 38.37(12) ?
C9 Ir1 Cl1 . . 163.07(9) ?
C9 Ir1 C2 . . 39.36(11) ?
C9 Ir1 C3 . . 65.48(12) ?
C9 Ir1 C10 . . 65.60(12) ?
C9 Ir1 C11 . . 38.92(12) ?
C10 Ir1 Cl1 . . 98.26(8) ?
C11 Ir1 Cl1 . . 130.92(9) ?
C11 Ir1 C10 . . 64.69(12) ?
C4 N2 Ir1 . . 125.7(2) ?
C4 N2 C8 . . 119.5(3) ?
C8 N2 Ir1 . . 114.85(19) ?
C12 N3 Ir1 . . 116.05(19) ?
C12 N3 C13 . . 120.5(2) ?
C13 N3 Ir1 . . 123.07(18) ?
C16 N4 C23 . . 119.5(3) ?
C16 N4 C24 . . 119.2(3) ?
C24 N4 C23 . . 117.9(3) ?
H1A C1 H1B . . 109.500000 ?
H1A C1 H1C . . 109.500000 ?
H1B C1 H1C . . 109.500000 ?
C11 C1 H1A . . 109.500000 ?
C11 C1 H1B . . 109.500000 ?
C11 C1 H1C . . 109.500000 ?
C9 C2 Ir1 . . 69.06(17) ?
C9 C2 C20 . . 126.3(3) ?
C10 C2 Ir1 . . 71.37(17) ?
C10 C2 C9 . . 108.9(3) ?
C10 C2 C20 . . 124.7(3) ?
C20 C2 Ir1 . . 127.3(2) ?
C10 C3 Ir1 . . 70.89(16) ?
C10 C3 C22 . . 125.4(3) ?
C11 C3 Ir1 . . 70.97(17) ?
C11 C3 C10 . . 107.9(3) ?
C11 C3 C22 . . 126.5(3) ?
C22 C3 Ir1 . . 127.9(2) ?
N2 C4 H4 . . 120.100000 ?
N2 C4 C5 . . 119.7(3) ?
C5 C4 H4 . . 120.100000 ?
F2 C5 C4 . . 118.4(3) ?
F2 C5 C6 . . 119.4(3) ?
C6 C5 C4 . . 122.2(3) ?
C5 C6 H6 . . 121.600000 ?
C5 C6 C7 . . 116.9(3) ?
C7 C6 H6 . . 121.600000 ?
C6 C7 H7 . . 120.100000 ?
C8 C7 C6 . . 119.9(3) ?
C8 C7 H7 . . 120.100000 ?
N2 C8 C7 . . 121.8(3) ?
N2 C8 C12 . . 116.1(2) ?
C7 C8 C12 . . 121.7(3) ?
C2 C9 Ir1 . . 71.58(17) ?
C2 C9 C19 . . 126.8(3) ?
C11 C9 Ir1 . . 72.00(17) ?
C11 C9 C2 . . 106.9(3) ?
C11 C9 C19 . . 126.1(3) ?
C19 C9 Ir1 . . 126.1(2) ?
C2 C10 Ir1 . . 70.43(17) ?
C2 C10 C3 . . 107.3(3) ?
C2 C10 C21 . . 126.0(3) ?
C3 C10 Ir1 . . 70.05(17) ?
C3 C10 C21 . . 126.6(3) ?
C21 C10 Ir1 . . 127.0(2) ?
C1 C11 Ir1 . . 127.7(2) ?
C3 C11 Ir1 . . 70.66(17) ?
C3 C11 C1 . . 126.1(3) ?
C3 C11 C9 . . 108.8(3) ?
C9 C11 Ir1 . . 69.08(17) ?
C9 C11 C1 . . 125.0(3) ?
O2 C12 N3 . . 128.4(3) ?
O2 C12 C8 . . 119.1(3) ?
N3 C12 C8 . . 112.3(2) ?
C14 C13 N3 . . 118.5(3) ?
C18 C13 N3 . . 124.1(3) ?
C18 C13 C14 . . 117.4(3) ?
C13 C14 H14 . . 119.100000 ?
C15 C14 C13 . . 121.9(3) ?
C15 C14 H14 . . 119.100000 ?
C14 C15 H15 . . 119.500000 ?
C14 C15 C16 . . 121.0(3) ?
C16 C15 H15 . . 119.500000 ?
N4 C16 C15 . . 121.0(3) ?
N4 C16 C17 . . 121.9(3) ?
C15 C16 C17 . . 117.1(3) ?
C16 C17 H17 . . 119.200000 ?
C18 C17 C16 . . 121.5(3) ?
C18 C17 H17 . . 119.200000 ?
C13 C18 H18 . . 119.500000 ?
C17 C18 C13 . . 121.1(3) ?
C17 C18 H18 . . 119.500000 ?
C9 C19 H19A . . 109.500000 ?
C9 C19 H19B . . 109.500000 ?
C9 C19 H19C . . 109.500000 ?
H19A C19 H19B . . 109.500000 ?
H19A C19 H19C . . 109.500000 ?
H19B C19 H19C . . 109.500000 ?
C2 C20 H20A . . 109.500000 ?
C2 C20 H20B . . 109.500000 ?
C2 C20 H20C . . 109.500000 ?
H20A C20 H20B . . 109.500000 ?
H20A C20 H20C . . 109.500000 ?
H20B C20 H20C . . 109.500000 ?
C10 C21 H21A . . 109.500000 ?
C10 C21 H21B . . 109.500000 ?
C10 C21 H21C . . 109.500000 ?
H21A C21 H21B . . 109.500000 ?
H21A C21 H21C . . 109.500000 ?
H21B C21 H21C . . 109.500000 ?
C3 C22 H22A . . 109.500000 ?
C3 C22 H22B . . 109.500000 ?
C3 C22 H22C . . 109.500000 ?
H22A C22 H22B . . 109.500000 ?
H22A C22 H22C . . 109.500000 ?
H22B C22 H22C . . 109.500000 ?
N4 C23 H23A . . 109.500000 ?
N4 C23 H23B . . 109.500000 ?
N4 C23 H23C . . 109.500000 ?
H23A C23 H23B . . 109.500000 ?
H23A C23 H23C . . 109.500000 ?
H23B C23 H23C . . 109.500000 ?
N4 C24 H24A . . 109.500000 ?
N4 C24 H24B . . 109.500000 ?
N4 C24 H24C . . 109.500000 ?
H24A C24 H24B . . 109.500000 ?
H24A C24 H24C . . 109.500000 ?
H24B C24 H24C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Ir1 N2 C4 C5 . . . . 177.6(2) ?
Ir1 N2 C8 C7 . . . . -176.6(2) ?
Ir1 N2 C8 C12 . . . . 9.6(3) ?
Ir1 N3 C12 O2 . . . . 166.6(3) ?
Ir1 N3 C12 C8 . . . . -18.6(3) ?
Ir1 N3 C13 C14 . . . . 47.8(3) ?
Ir1 N3 C13 C18 . . . . -131.3(3) ?
Ir1 C2 C9 C11 . . . . -63.8(2) ?
Ir1 C2 C9 C19 . . . . 121.8(3) ?
Ir1 C2 C10 C3 . . . . 60.6(2) ?
Ir1 C2 C10 C21 . . . . -122.0(3) ?
Ir1 C3 C10 C2 . . . . -60.9(2) ?
Ir1 C3 C10 C21 . . . . 121.8(3) ?
Ir1 C3 C11 C1 . . . . -123.1(3) ?
Ir1 C3 C11 C9 . . . . 58.7(2) ?
Ir1 C9 C11 C1 . . . . 122.1(3) ?
Ir1 C9 C11 C3 . . . . -59.7(2) ?
F2 C5 C6 C7 . . . . -178.1(3) ?
N2 C4 C5 F2 . . . . 179.1(3) ?
N2 C4 C5 C6 . . . . -0.2(5) ?
N2 C8 C12 O2 . . . . -178.8(3) ?
N2 C8 C12 N3 . . . . 5.9(4) ?
N3 C13 C14 C15 . . . . -178.6(3) ?
N3 C13 C18 C17 . . . . 179.1(3) ?
N4 C16 C17 C18 . . . . -178.2(3) ?
C2 C9 C11 Ir1 . . . . 63.5(2) ?
C2 C9 C11 C1 . . . . -174.4(3) ?
C2 C9 C11 C3 . . . . 3.8(3) ?
C4 N2 C8 C7 . . . . 2.9(4) ?
C4 N2 C8 C12 . . . . -170.9(3) ?
C4 C5 C6 C7 . . . . 1.2(5) ?
C5 C6 C7 C8 . . . . -0.3(5) ?
C6 C7 C8 N2 . . . . -1.8(5) ?
C6 C7 C8 C12 . . . . 171.6(3) ?
C7 C8 C12 O2 . . . . 7.4(4) ?
C7 C8 C12 N3 . . . . -167.9(3) ?
C8 N2 C4 C5 . . . . -1.9(4) ?
C9 C2 C10 Ir1 . . . . -59.0(2) ?
C9 C2 C10 C3 . . . . 1.6(3) ?
C9 C2 C10 C21 . . . . 178.9(3) ?
C10 C2 C9 Ir1 . . . . 60.5(2) ?
C10 C2 C9 C11 . . . . -3.4(3) ?
C10 C2 C9 C19 . . . . -177.7(3) ?
C10 C3 C11 Ir1 . . . . -61.6(2) ?
C10 C3 C11 C1 . . . . 175.3(3) ?
C10 C3 C11 C9 . . . . -2.9(3) ?
C11 C3 C10 Ir1 . . . . 61.7(2) ?
C11 C3 C10 C2 . . . . 0.8(3) ?
C11 C3 C10 C21 . . . . -176.5(3) ?
C12 N3 C13 C14 . . . . -139.5(3) ?
C12 N3 C13 C18 . . . . 41.4(4) ?
C13 N3 C12 O2 . . . . -6.6(5) ?
C13 N3 C12 C8 . . . . 168.2(2) ?
C13 C14 C15 C16 . . . . -0.2(5) ?
C14 C13 C18 C17 . . . . 0.0(5) ?
C14 C15 C16 N4 . . . . 178.7(3) ?
C14 C15 C16 C17 . . . . -0.6(5) ?
C15 C16 C17 C18 . . . . 1.1(5) ?
C16 C17 C18 C13 . . . . -0.8(5) ?
C18 C13 C14 C15 . . . . 0.5(5) ?
C19 C9 C11 Ir1 . . . . -122.0(3) ?
C19 C9 C11 C1 . . . . 0.1(5) ?
C19 C9 C11 C3 . . . . 178.3(3) ?
C20 C2 C9 Ir1 . . . . -121.6(3) ?
C20 C2 C9 C11 . . . . 174.5(3) ?
C20 C2 C9 C19 . . . . 0.2(5) ?
C20 C2 C10 Ir1 . . . . 123.0(3) ?
C20 C2 C10 C3 . . . . -176.4(3) ?
C20 C2 C10 C21 . . . . 1.0(5) ?
C22 C3 C10 Ir1 . . . . -123.4(3) ?
C22 C3 C10 C2 . . . . 175.7(3) ?
C22 C3 C10 C21 . . . . -1.6(5) ?
C22 C3 C11 Ir1 . . . . 123.5(3) ?
C22 C3 C11 C1 . . . . 0.4(5) ?
C22 C3 C11 C9 . . . . -177.7(3) ?
C23 N4 C16 C15 . . . . 6.6(5) ?
C23 N4 C16 C17 . . . . -174.1(3) ?
C24 N4 C16 C15 . . . . 165.6(3) ?
C24 N4 C16 C17 . . . . -15.1(5) ?

