# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ga_220107a_a
_database_code_depnum_ccdc_archive 'CCDC 2180605'
loop_
_audit_author_name
_audit_author_address
'Zi-Jian Yao'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2022-06-21 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H28 Cl Ir N2 O'
_chemical_formula_weight         600.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -5.7005 5.2682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6120(3)
_cell_length_b                   11.8772(4)
_cell_length_c                   22.7340(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.7960(10)
_cell_angle_gamma                90
_cell_volume                     2303.89(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    174(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      4.60
_cell_measurement_theta_max      59.37

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    8.242
_shelx_estimated_absorpt_T_min   0.232
_shelx_estimated_absorpt_T_max   0.319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      174(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31774
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         4.599
_diffrn_reflns_theta_max         58.995
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4974
_reflns_number_gt                4755
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0494P)²+2.1846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4974
_refine_ls_number_parameters     321
_refine_ls_number_restraints     253
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.34077(2) 0.69229(2) 0.58032(2) 0.01918(7) Uani 1 1 d . . . . .
Cl1 Cl 0.59861(9) 0.74282(6) 0.55869(3) 0.02774(16) Uani 1 1 d . . . . .
O1 O 0.4558(3) 0.56313(17) 0.62821(10) 0.0259(5) Uani 1 1 d . . . . .
N1 N 0.4636(4) 0.6820(2) 0.70901(13) 0.0275(6) Uani 1 1 d . . . . .
N2 N 0.4026(3) 0.7624(2) 0.66613(11) 0.0224(5) Uani 1 1 d . . . . .
C1 C 0.4893(4) 0.5859(3) 0.68426(14) 0.0252(6) Uani 1 1 d D . . . .
C2 C 0.555(3) 0.4846(19) 0.7197(10) 0.025(3) Uani 0.44(5) 1 d . U P A 1
C3 C 0.527(3) 0.3767(17) 0.6986(11) 0.028(3) Uani 0.44(5) 1 d . U P A 1
H3 H 0.466802 0.364549 0.660909 0.034 Uiso 0.44(5) 1 calc R U P A 1
C4 C 0.587(3) 0.2846(18) 0.7334(11) 0.033(3) Uani 0.44(5) 1 d . U P A 1
H4 H 0.566822 0.210012 0.719342 0.040 Uiso 0.44(5) 1 calc R U P A 1
C5 C 0.676(2) 0.302(2) 0.7874(11) 0.030(3) Uani 0.44(5) 1 d . U P A 1
H5 H 0.718543 0.239766 0.810380 0.036 Uiso 0.44(5) 1 calc R U P A 1
C6 C 0.703(2) 0.409(2) 0.8081(8) 0.027(3) Uani 0.44(5) 1 d . U P A 1
H6 H 0.764341 0.419770 0.845740 0.033 Uiso 0.44(5) 1 calc R U P A 1
C7 C 0.644(3) 0.502(2) 0.7754(10) 0.032(3) Uani 0.44(5) 1 d . U P A 1
H7 H 0.662850 0.575475 0.790543 0.038 Uiso 0.44(5) 1 calc R U P A 1
C2' C 0.561(2) 0.4994(13) 0.7255(7) 0.026(3) Uani 0.56(5) 1 d DG U P A 2
C3' C 0.543(2) 0.3877(14) 0.7078(8) 0.031(3) Uani 0.56(5) 1 d G U P A 2
H3' H 0.484972 0.369628 0.670414 0.037 Uiso 0.56(5) 1 calc R U P A 2
C4' C 0.610(2) 0.3025(14) 0.7447(8) 0.033(3) Uani 0.56(5) 1 d G U P A 2
H4' H 0.597393 0.226067 0.732587 0.040 Uiso 0.56(5) 1 calc R U P A 2
C5' C 0.6948(18) 0.3289(15) 0.7993(8) 0.030(3) Uani 0.56(5) 1 d G U P A 2
H5' H 0.740483 0.270596 0.824558 0.036 Uiso 0.56(5) 1 calc R U P A 2
C6' C 0.7130(17) 0.4406(17) 0.8170(7) 0.031(3) Uani 0.56(5) 1 d G U P A 2
H6' H 0.771129 0.458686 0.854366 0.038 Uiso 0.56(5) 1 calc R U P A 2
C7' C 0.646(2) 0.5259(14) 0.7801(7) 0.029(3) Uani 0.56(5) 1 d G U P A 2
H7' H 0.658705 0.602251 0.792201 0.035 Uiso 0.56(5) 1 calc R U P A 2
C8 C 0.4316(6) 0.8820(4) 0.75427(17) 0.0460(10) Uani 1 1 d . . . . .
H8A H 0.350749 0.848225 0.775132 0.069 Uiso 1 1 calc R U . . .
H8B H 0.437067 0.963134 0.762197 0.069 Uiso 1 1 calc R U . . .
H8C H 0.533240 0.847476 0.768260 0.069 Uiso 1 1 calc R U . . .
C9 C 0.3911(4) 0.8624(3) 0.68836(14) 0.0269(7) Uani 1 1 d . . . . .
C10 C 0.3386(4) 0.9613(3) 0.65151(15) 0.0289(7) Uani 1 1 d . . . . .
C11 C 0.3941(4) 0.9818(3) 0.59804(16) 0.0322(7) Uani 1 1 d . . . . .
H11 H 0.464229 0.930287 0.583494 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3461(5) 1.0790(3) 0.5656(2) 0.0413(9) Uani 1 1 d . . . . .
H12 H 0.384998 1.093788 0.529177 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2426(6) 1.1534(3) 0.5862(2) 0.0516(11) Uani 1 1 d . . . . .
H13 H 0.208442 1.218211 0.563551 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1887(6) 1.1330(3) 0.6400(2) 0.0549(12) Uani 1 1 d . . . . .
H14 H 0.118107 1.184422 0.654376 0.066 Uiso 1 1 calc R U . . .
C15 C 0.2371(5) 1.0387(3) 0.67272(19) 0.0393(8) Uani 1 1 d . . . . .
H15 H 0.201343 1.026229 0.709910 0.047 Uiso 1 1 calc R U . . .
C16 C 0.0988(4) 0.6467(3) 0.57232(14) 0.0244(6) Uani 1 1 d . . . . .
C17 C 0.1084(4) 0.7601(2) 0.54944(14) 0.0236(6) Uani 1 1 d . . . . .
C18 C 0.1976(4) 0.7575(3) 0.50124(14) 0.0258(7) Uani 1 1 d . . . . .
C19 C 0.2430(4) 0.6416(3) 0.49221(14) 0.0266(7) Uani 1 1 d . . . . .
C20 C 0.1786(4) 0.5740(3) 0.53520(15) 0.0258(6) Uani 1 1 d . . . . .
C21 C 0.0076(5) 0.6108(3) 0.62016(16) 0.0356(8) Uani 1 1 d . . . . .
H21A H -0.103935 0.606853 0.604325 0.053 Uiso 1 1 calc R U . . .
H21B H 0.022791 0.665412 0.652756 0.053 Uiso 1 1 calc R U . . .
H21C H 0.043835 0.536513 0.634918 0.053 Uiso 1 1 calc R U . . .
C22 C 0.0236(4) 0.8592(3) 0.57070(17) 0.0330(7) Uani 1 1 d . . . . .
H22A H 0.067065 0.928869 0.556630 0.049 Uiso 1 1 calc R U . . .
H22B H 0.036330 0.859225 0.614198 0.049 Uiso 1 1 calc R U . . .
H22C H -0.088053 0.854161 0.555185 0.049 Uiso 1 1 calc R U . . .
C23 C 0.2281(5) 0.8530(3) 0.46172(17) 0.0373(8) Uani 1 1 d . . . . .
H23A H 0.158283 0.846950 0.424054 0.056 Uiso 1 1 calc R U . . .
H23B H 0.337362 0.850303 0.454111 0.056 Uiso 1 1 calc R U . . .
H23C H 0.208712 0.924383 0.481056 0.056 Uiso 1 1 calc R U . . .
C24 C 0.3321(4) 0.6021(3) 0.44430(15) 0.0378(8) Uani 1 1 d . . . . .
H24A H 0.372872 0.526228 0.453797 0.057 Uiso 1 1 calc R U . . .
H24B H 0.419519 0.653521 0.441158 0.057 Uiso 1 1 calc R U . . .
H24C H 0.262428 0.600396 0.406461 0.057 Uiso 1 1 calc R U . . .
C25 C 0.1973(4) 0.4501(3) 0.54345(17) 0.0340(8) Uani 1 1 d . . . . .
H25A H 0.270869 0.421621 0.517681 0.051 Uiso 1 1 calc R U . . .
H25B H 0.095392 0.413274 0.533136 0.051 Uiso 1 1 calc R U . . .
H25C H 0.237802 0.433939 0.584974 0.051 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 2.056(2) . ?
Ir1 N2 2.122(2) . ?
Ir1 C16 2.137(3) . ?
Ir1 C20 2.142(3) . ?
Ir1 C19 2.151(3) . ?
Ir1 C18 2.179(3) . ?
Ir1 C17 2.183(3) . ?
Ir1 Cl1 2.4144(8) . ?
O1 C1 1.296(4) . ?
N1 C1 1.305(4) . ?
N1 N2 1.415(4) . ?
N2 C9 1.299(4) . ?
C1 C2' 1.469(11) . ?
C1 C2 1.515(16) . ?
C2 C3 1.38(2) . ?
C2 C7 1.400(17) . ?
C3 C4 1.407(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.37(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.359(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(18) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C2' C3' 1.389(6) . ?
C2' C7' 1.389(6) . ?
C3' C4' 1.389(6) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.389(6) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.389(6) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.389(6) . ?
C6' H6' 0.9500 . ?
C7' H7' 0.9500 . ?
C8 C9 1.510(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.478(5) . ?
C10 C11 1.387(5) . ?
C10 C15 1.399(5) . ?
C11 C12 1.402(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C20 1.445(4) . ?
C16 C17 1.450(4) . ?
C16 C21 1.488(5) . ?
C17 C18 1.422(5) . ?
C17 C22 1.499(4) . ?
C18 C19 1.453(5) . ?
C18 C23 1.492(5) . ?
C19 C20 1.433(5) . ?
C19 C24 1.491(5) . ?
C20 C25 1.490(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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 N2 76.32(9) . . ?
O1 Ir1 C16 104.50(11) . . ?
N2 Ir1 C16 107.33(11) . . ?
O1 Ir1 C20 90.02(11) . . ?
N2 Ir1 C20 139.82(12) . . ?
C16 Ir1 C20 39.48(12) . . ?
O1 Ir1 C19 112.58(11) . . ?
N2 Ir1 C19 169.71(11) . . ?
C16 Ir1 C19 66.16(13) . . ?
C20 Ir1 C19 39.01(13) . . ?
O1 Ir1 C18 151.61(11) . . ?
N2 Ir1 C18 131.48(12) . . ?
C16 Ir1 C18 65.39(12) . . ?
C20 Ir1 C18 65.08(12) . . ?
C19 Ir1 C18 39.19(13) . . ?
O1 Ir1 C17 143.17(11) . . ?
N2 Ir1 C17 104.80(11) . . ?
C16 Ir1 C17 39.21(11) . . ?
C20 Ir1 C17 65.06(11) . . ?
C19 Ir1 C17 65.03(12) . . ?
C18 Ir1 C17 38.03(13) . . ?
O1 Ir1 Cl1 84.44(7) . . ?
N2 Ir1 Cl1 88.09(7) . . ?
C16 Ir1 Cl1 163.52(9) . . ?
C20 Ir1 Cl1 128.56(9) . . ?
C19 Ir1 Cl1 97.73(9) . . ?
C18 Ir1 Cl1 100.17(9) . . ?
C17 Ir1 Cl1 132.15(9) . . ?
C1 O1 Ir1 113.09(19) . . ?
C1 N1 N2 111.3(3) . . ?
C9 N2 N1 113.0(3) . . ?
C9 N2 Ir1 133.9(2) . . ?
N1 N2 Ir1 113.06(18) . . ?
O1 C1 N1 125.3(3) . . ?
O1 C1 C2' 120.0(8) . . ?
N1 C1 C2' 114.7(8) . . ?
O1 C1 C2 112.0(10) . . ?
N1 C1 C2 122.6(11) . . ?
C3 C2 C7 119.8(10) . . ?
C3 C2 C1 121.1(14) . . ?
C7 C2 C1 119.1(16) . . ?
C2 C3 C4 119.5(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.3(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.0(10) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.3(11) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 119.1(13) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C3' C2' C7' 120.0 . . ?
C3' C2' C1 117.5(9) . . ?
C7' C2' C1 122.5(9) . . ?
C2' C3' C4' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C5' C4' C3' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C3' C4' H4' 120.0 . . ?
C4' C5' C6' 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
C7' C6' C5' 120.0 . . ?
C7' C6' H6' 120.0 . . ?
C5' C6' H6' 120.0 . . ?
C6' C7' C2' 120.0 . . ?
C6' C7' H7' 120.0 . . ?
C2' C7' H7' 120.0 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 122.6(3) . . ?
N2 C9 C8 120.5(3) . . ?
C10 C9 C8 116.8(3) . . ?
C11 C10 C15 119.5(3) . . ?
C11 C10 C9 121.4(3) . . ?
C15 C10 C9 119.0(3) . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C20 C16 C17 106.9(3) . . ?
C20 C16 C21 126.6(3) . . ?
C17 C16 C21 126.2(3) . . ?
C20 C16 Ir1 70.43(18) . . ?
C17 C16 Ir1 72.12(17) . . ?
C21 C16 Ir1 128.0(2) . . ?
C18 C17 C16 108.6(3) . . ?
C18 C17 C22 127.2(3) . . ?
C16 C17 C22 124.0(3) . . ?
C18 C17 Ir1 70.83(17) . . ?
C16 C17 Ir1 68.67(16) . . ?
C22 C17 Ir1 130.6(2) . . ?
C17 C18 C19 108.3(3) . . ?
C17 C18 C23 127.2(3) . . ?
C19 C18 C23 124.2(3) . . ?
C17 C18 Ir1 71.13(17) . . ?
C19 C18 Ir1 69.34(15) . . ?
C23 C18 Ir1 129.8(2) . . ?
C20 C19 C18 107.3(3) . . ?
C20 C19 C24 127.4(3) . . ?
C18 C19 C24 125.2(3) . . ?
C20 C19 Ir1 70.15(17) . . ?
C18 C19 Ir1 71.46(16) . . ?
C24 C19 Ir1 126.4(2) . . ?
C19 C20 C16 108.8(3) . . ?
C19 C20 C25 126.5(3) . . ?
C16 C20 C25 124.6(3) . . ?
C19 C20 Ir1 70.85(17) . . ?
C16 C20 Ir1 70.09(17) . . ?
C25 C20 Ir1 122.4(2) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C1 N1 N2 C9 -173.2(3) . . . . ?
C1 N1 N2 Ir1 9.3(3) . . . . ?
Ir1 O1 C1 N1 -4.0(4) . . . . ?
Ir1 O1 C1 C2' 175.5(11) . . . . ?
Ir1 O1 C1 C2 172.8(13) . . . . ?
N2 N1 C1 O1 -3.7(5) . . . . ?
N2 N1 C1 C2' 176.7(10) . . . . ?
N2 N1 C1 C2 179.8(14) . . . . ?
O1 C1 C2 C3 -22(2) . . . . ?
N1 C1 C2 C3 154.8(12) . . . . ?
O1 C1 C2 C7 159.1(12) . . . . ?
N1 C1 C2 C7 -24(2) . . . . ?
C7 C2 C3 C4 0.0(15) . . . . ?
C1 C2 C3 C4 -179(2) . . . . ?
C2 C3 C4 C5 -1.0(16) . . . . ?
C3 C4 C5 C6 1.2(18) . . . . ?
C4 C5 C6 C7 -0.4(17) . . . . ?
C5 C6 C7 C2 -0.6(16) . . . . ?
C3 C2 C7 C6 0.8(15) . . . . ?
C1 C2 C7 C6 180(2) . . . . ?
O1 C1 C2' C3' -21.3(14) . . . . ?
N1 C1 C2' C3' 158.3(7) . . . . ?
O1 C1 C2' C7' 158.0(8) . . . . ?
N1 C1 C2' C7' -22.4(15) . . . . ?
C7' C2' C3' C4' 0.0 . . . . ?
C1 C2' C3' C4' 179.4(17) . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C3' C4' C5' C6' 0.0 . . . . ?
C4' C5' C6' C7' 0.0 . . . . ?
C5' C6' C7' C2' 0.0 . . . . ?
C3' C2' C7' C6' 0.0 . . . . ?
C1 C2' C7' C6' -179.4(18) . . . . ?
N1 N2 C9 C10 176.5(3) . . . . ?
Ir1 N2 C9 C10 -6.6(5) . . . . ?
N1 N2 C9 C8 -3.5(5) . . . . ?
Ir1 N2 C9 C8 173.4(3) . . . . ?
N2 C9 C10 C11 -44.2(5) . . . . ?
C8 C9 C10 C11 135.9(4) . . . . ?
N2 C9 C10 C15 139.2(4) . . . . ?
C8 C9 C10 C15 -40.7(5) . . . . ?
C15 C10 C11 C12 -0.9(5) . . . . ?
C9 C10 C11 C12 -177.5(3) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C11 C12 C13 C14 1.5(6) . . . . ?
C12 C13 C14 C15 -0.5(7) . . . . ?
C13 C14 C15 C10 -1.3(6) . . . . ?
C11 C10 C15 C14 1.9(6) . . . . ?
C9 C10 C15 C14 178.6(4) . . . . ?
C20 C16 C17 C18 -2.5(3) . . . . ?
C21 C16 C17 C18 -175.8(3) . . . . ?
Ir1 C16 C17 C18 59.8(2) . . . . ?
C20 C16 C17 C22 172.3(3) . . . . ?
C21 C16 C17 C22 -1.0(5) . . . . ?
Ir1 C16 C17 C22 -125.5(3) . . . . ?
C20 C16 C17 Ir1 -62.2(2) . . . . ?
C21 C16 C17 Ir1 124.4(3) . . . . ?
C16 C17 C18 C19 1.2(3) . . . . ?
C22 C17 C18 C19 -173.4(3) . . . . ?
Ir1 C17 C18 C19 59.6(2) . . . . ?
C16 C17 C18 C23 175.4(3) . . . . ?
C22 C17 C18 C23 0.8(5) . . . . ?
Ir1 C17 C18 C23 -126.2(3) . . . . ?
C16 C17 C18 Ir1 -58.5(2) . . . . ?
C22 C17 C18 Ir1 127.0(3) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C23 C18 C19 C20 -173.8(3) . . . . ?
Ir1 C18 C19 C20 61.3(2) . . . . ?
C17 C18 C19 C24 177.3(3) . . . . ?
C23 C18 C19 C24 2.9(5) . . . . ?
Ir1 C18 C19 C24 -122.0(3) . . . . ?
C17 C18 C19 Ir1 -60.7(2) . . . . ?
C23 C18 C19 Ir1 124.8(3) . . . . ?
C18 C19 C20 C16 -2.1(3) . . . . ?
C24 C19 C20 C16 -178.7(3) . . . . ?
Ir1 C19 C20 C16 60.0(2) . . . . ?
C18 C19 C20 C25 -178.8(3) . . . . ?
C24 C19 C20 C25 4.6(5) . . . . ?
Ir1 C19 C20 C25 -116.6(3) . . . . ?
C18 C19 C20 Ir1 -62.2(2) . . . . ?
C24 C19 C20 Ir1 121.2(3) . . . . ?
C17 C16 C20 C19 2.8(3) . . . . ?
C21 C16 C20 C19 176.1(3) . . . . ?
Ir1 C16 C20 C19 -60.5(2) . . . . ?
C17 C16 C20 C25 179.6(3) . . . . ?
C21 C16 C20 C25 -7.1(5) . . . . ?
Ir1 C16 C20 C25 116.2(3) . . . . ?
C17 C16 C20 Ir1 63.4(2) . . . . ?
C21 C16 C20 Ir1 -123.4(3) . . . . ?

_refine_diff_density_max         3.186
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.136

