# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_18022
_database_code_depnum_ccdc_archive 'CCDC 2085491'
_audit_update_record             
;
2021-05-24 deposited with the CCDC.	2021-08-31 downloaded from the CCDC.
;

_vrf_PLAT971_I                   
;
PROBLEM : Check Calcd Resid. Dens. 0.95A From Ir1 2.74 eA-3 
RESPONSE:... The electron density is very close to the Ir metal centre.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H29 Cl2 Ir N2 O'
_chemical_formula_sum            'C22 H29 Cl2 Ir N2 O'
_chemical_formula_weight         600.57

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'
N N 0.0061 0.0033 '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'
Ir Ir -1.4442 7.9887 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -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'

_cell_length_a                   11.369(6)
_cell_length_b                   8.613(5)
_cell_length_c                   12.615(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.248(8)
_cell_angle_gamma                90
_cell_volume                     1117.2(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    928
_cell_measurement_theta_min      2.964
_cell_measurement_theta_max      28.005

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    6.229
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.436
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_process_details   
;
absoprtion correction based on 7497 reflections(SADABS);Rint 0.1553 before
correction and 0.0683 after.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8857
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_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 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4624
_reflns_number_gt                4390
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_max     0.905
_reflns_Friedel_fraction_full    0.939

_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²] 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_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.035(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4624
_refine_ls_number_parameters     261
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_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 1.00036(3) 0.20903(3) 0.25028(3) 0.01550(12) Uani 1 1 d . . . . .
Cl1 Cl 0.9055(3) -0.0277(3) 0.1459(2) 0.0233(6) Uani 1 1 d . . . . .
Cl2 Cl 0.9266(3) 0.3256(4) 0.0591(3) 0.0289(7) Uani 1 1 d . . . . .
O1 O 0.4622(9) -0.3524(12) 0.3555(9) 0.038(2) Uani 1 1 d . . . . .
N1 N 0.7592(11) 0.1813(14) 0.2983(10) 0.029(2) Uani 1 1 d . . . . .
N2 N 0.7789(12) 0.4148(14) 0.2499(11) 0.038(3) Uani 1 1 d . . . . .
C1 C 0.8325(14) 0.2699(16) 0.2624(14) 0.024(3) Uani 1 1 d . . . . .
C2 C 0.6780(17) 0.413(2) 0.2815(17) 0.057(5) Uani 1 1 d . . . . .
H2 H 0.626894 0.499319 0.282581 0.068 Uiso 1 1 calc R U . . .
C3 C 0.6643(17) 0.270(2) 0.3101(18) 0.050(4) Uani 1 1 d . . . . .
H3 H 0.600707 0.234437 0.334498 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7815(12) 0.0184(16) 0.3333(11) 0.028(3) Uani 1 1 d . . . . .
H4A H 0.814704 0.010989 0.419582 0.034 Uiso 1 1 calc R U . . .
H4B H 0.848605 -0.024693 0.311154 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6586(12) -0.0767(15) 0.2763(11) 0.025(3) Uani 1 1 d . . . . .
C6 C 0.5871(13) -0.0822(18) 0.1545(11) 0.034(3) Uani 1 1 d . . . . .
H6 H 0.614579 -0.021646 0.106187 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4795(14) -0.1724(18) 0.1039(12) 0.038(3) Uani 1 1 d . . . . .
H7 H 0.432565 -0.175498 0.021062 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4381(16) -0.261(2) 0.1748(16) 0.035(4) Uani 1 1 d . . . . .
H8 H 0.362366 -0.323344 0.140260 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5082(15) -0.256(2) 0.2958(14) 0.028(3) Uani 1 1 d . . . . .
C10 C 0.6160(12) -0.1651(14) 0.3459(11) 0.022(2) Uani 1 1 d . . . . .
H10 H 0.662428 -0.161638 0.428790 0.027 Uiso 1 1 calc R U . . .
C11 C 0.8254(16) 0.5591(16) 0.2203(16) 0.048(4) Uani 1 1 d . . . . .
H11A H 0.853685 0.630223 0.287206 0.072 Uiso 1 1 calc R U . . .
H11B H 0.755036 0.607200 0.152436 0.072 Uiso 1 1 calc R U . . .
H11C H 0.898778 0.536579 0.201319 0.072 Uiso 1 1 calc R U . . .
C12 C 1.1123(12) 0.2558(15) 0.4333(11) 0.018(2) Uani 1 1 d . . . . .
C13 C 1.1525(11) 0.3605(13) 0.3639(9) 0.017(2) Uani 1 1 d . . . . .
C14 C 1.2091(13) 0.2663(15) 0.3021(13) 0.020(2) Uani 1 1 d . . . . .
C15 C 1.2009(12) 0.1098(14) 0.3282(10) 0.023(2) Uani 1 1 d . . . . .
C16 C 1.1374(12) 0.0985(12) 0.4082(9) 0.020(2) Uani 1 1 d . . . . .
C17 C 1.0615(14) 0.3025(14) 0.5177(13) 0.028(3) Uani 1 1 d . . . . .
H17A H 1.002843 0.221913 0.521979 0.041 Uiso 1 1 calc R U . . .
H17B H 1.013791 0.400490 0.492289 0.041 Uiso 1 1 calc R U . . .
H17C H 1.133922 0.316388 0.595102 0.041 Uiso 1 1 calc R U . . .
C18 C 1.1593(13) 0.5345(13) 0.3718(12) 0.029(3) Uani 1 1 d . . . . .
H18A H 1.248987 0.566566 0.420976 0.043 Uiso 1 1 calc R U . . .
H18B H 1.102193 0.572035 0.406528 0.043 Uiso 1 1 calc R U . . .
H18C H 1.131261 0.578584 0.293157 0.043 Uiso 1 1 calc R U . . .
C19 C 1.2675(14) 0.3297(16) 0.2248(12) 0.028(3) Uani 1 1 d . . . . .
H19A H 1.300807 0.243893 0.194300 0.043 Uiso 1 1 calc R U . . .
H19B H 1.339072 0.400142 0.270168 0.043 Uiso 1 1 calc R U . . .
H19C H 1.201027 0.386407 0.159278 0.043 Uiso 1 1 calc R U . . .
C20 C 1.2483(13) -0.0306(15) 0.2889(11) 0.029(3) Uani 1 1 d . . . . .
H20A H 1.174485 -0.098278 0.243885 0.043 Uiso 1 1 calc R U . . .
H20B H 1.310341 -0.086811 0.357498 0.043 Uiso 1 1 calc R U . . .
H20C H 1.291222 0.001228 0.239527 0.043 Uiso 1 1 calc R U . . .
C21 C 1.1225(13) -0.0465(14) 0.4641(11) 0.028(3) Uani 1 1 d . . . . .
H21A H 1.208480 -0.085690 0.517240 0.042 Uiso 1 1 calc R U . . .
H21B H 1.077628 -0.124312 0.403527 0.042 Uiso 1 1 calc R U . . .
H21C H 1.071436 -0.025560 0.508486 0.042 Uiso 1 1 calc R U . . .
C22 C 0.5391(15) -0.360(2) 0.4798(14) 0.045(4) Uani 1 1 d . . . . .
H22A H 0.629583 -0.383255 0.495993 0.067 Uiso 1 1 calc R U . . .
H22B H 0.505214 -0.442139 0.512993 0.067 Uiso 1 1 calc R U . . .
H22C H 0.535007 -0.260257 0.515302 0.067 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 C1 2.047(13) . ?
Ir1 C12 2.146(12) . ?
Ir1 C13 2.152(12) . ?
Ir1 C16 2.158(11) . ?
Ir1 C14 2.231(12) . ?
Ir1 C15 2.232(12) . ?
Ir1 Cl2 2.409(4) . ?
Ir1 Cl1 2.417(3) . ?
O1 C9 1.36(2) . ?
O1 C22 1.435(18) . ?
N1 C1 1.343(19) . ?
N1 C3 1.382(19) . ?
N1 C4 1.460(18) . ?
N2 C2 1.37(2) . ?
N2 C1 1.368(17) . ?
N2 C11 1.46(2) . ?
C2 C3 1.31(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.511(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.395(18) . ?
C5 C6 1.400(17) . ?
C6 C7 1.36(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.40(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.39(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.36(2) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C16 1.447(17) . ?
C12 C13 1.460(16) . ?
C12 C17 1.468(19) . ?
C13 C14 1.452(16) . ?
C13 C18 1.502(15) . ?
C14 C15 1.400(18) . ?
C14 C19 1.498(19) . ?
C15 C16 1.474(17) . ?
C15 C20 1.492(16) . ?
C16 C21 1.478(15) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C1 Ir1 C12 90.9(6) . . ?
C1 Ir1 C13 107.8(5) . . ?
C12 Ir1 C13 39.7(4) . . ?
C1 Ir1 C16 111.9(6) . . ?
C12 Ir1 C16 39.3(5) . . ?
C13 Ir1 C16 66.1(4) . . ?
C1 Ir1 C14 146.2(4) . . ?
C12 Ir1 C14 64.9(5) . . ?
C13 Ir1 C14 38.6(4) . . ?
C16 Ir1 C14 64.4(5) . . ?
C1 Ir1 C15 151.0(6) . . ?
C12 Ir1 C15 64.7(5) . . ?
C13 Ir1 C15 63.8(4) . . ?
C16 Ir1 C15 39.2(4) . . ?
C14 Ir1 C15 36.6(5) . . ?
C1 Ir1 Cl2 91.7(5) . . ?
C12 Ir1 Cl2 142.4(4) . . ?
C13 Ir1 Cl2 104.6(3) . . ?
C16 Ir1 Cl2 156.1(3) . . ?
C14 Ir1 Cl2 94.2(4) . . ?
C15 Ir1 Cl2 117.0(3) . . ?
C1 Ir1 Cl1 92.5(4) . . ?
C12 Ir1 Cl1 131.8(3) . . ?
C13 Ir1 Cl1 156.8(3) . . ?
C16 Ir1 Cl1 96.3(3) . . ?
C14 Ir1 Cl1 121.2(3) . . ?
C15 Ir1 Cl1 93.0(3) . . ?
Cl2 Ir1 Cl1 85.54(12) . . ?
C9 O1 C22 115.6(11) . . ?
C1 N1 C3 110.3(14) . . ?
C1 N1 C4 126.5(11) . . ?
C3 N1 C4 122.9(13) . . ?
C2 N2 C1 110.0(14) . . ?
C2 N2 C11 121.9(13) . . ?
C1 N2 C11 127.8(13) . . ?
N1 C1 N2 104.3(12) . . ?
N1 C1 Ir1 127.7(10) . . ?
N2 C1 Ir1 127.5(11) . . ?
C3 C2 N2 107.9(14) . . ?
C3 C2 H2 126.0 . . ?
N2 C2 H2 126.0 . . ?
C2 C3 N1 107.4(16) . . ?
C2 C3 H3 126.3 . . ?
N1 C3 H3 126.3 . . ?
N1 C4 C5 111.8(10) . . ?
N1 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C10 C5 C6 118.5(12) . . ?
C10 C5 C4 119.7(11) . . ?
C6 C5 C4 121.8(11) . . ?
C7 C6 C5 121.3(13) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.5(13) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 119.7(16) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 O1 125.1(14) . . ?
C10 C9 C8 120.4(15) . . ?
O1 C9 C8 114.5(16) . . ?
C9 C10 C5 120.5(13) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C12 C13 107.8(11) . . ?
C16 C12 C17 126.2(11) . . ?
C13 C12 C17 125.9(12) . . ?
C16 C12 Ir1 70.8(6) . . ?
C13 C12 Ir1 70.4(7) . . ?
C17 C12 Ir1 126.6(9) . . ?
C14 C13 C12 107.5(10) . . ?
C14 C13 C18 124.9(11) . . ?
C12 C13 C18 126.7(11) . . ?
C14 C13 Ir1 73.6(7) . . ?
C12 C13 Ir1 69.9(7) . . ?
C18 C13 Ir1 130.8(8) . . ?
C15 C14 C13 108.8(11) . . ?
C15 C14 C19 126.6(12) . . ?
C13 C14 C19 124.6(11) . . ?
C15 C14 Ir1 71.7(7) . . ?
C13 C14 Ir1 67.7(7) . . ?
C19 C14 Ir1 127.0(10) . . ?
C14 C15 C16 109.1(10) . . ?
C14 C15 C20 129.2(11) . . ?
C16 C15 C20 121.7(10) . . ?
C14 C15 Ir1 71.7(7) . . ?
C16 C15 Ir1 67.7(6) . . ?
C20 C15 Ir1 127.6(9) . . ?
C12 C16 C15 106.7(9) . . ?
C12 C16 C21 127.8(11) . . ?
C15 C16 C21 124.9(10) . . ?
C12 C16 Ir1 69.9(6) . . ?
C15 C16 Ir1 73.1(6) . . ?
C21 C16 Ir1 128.9(9) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 N1 C1 N2 -1.2(17) . . . . ?
C4 N1 C1 N2 -174.9(12) . . . . ?
C3 N1 C1 Ir1 171.4(12) . . . . ?
C4 N1 C1 Ir1 -2(2) . . . . ?
C2 N2 C1 N1 1.9(17) . . . . ?
C11 N2 C1 N1 175.4(14) . . . . ?
C2 N2 C1 Ir1 -170.8(12) . . . . ?
C11 N2 C1 Ir1 3(2) . . . . ?
C1 N2 C2 C3 -2(2) . . . . ?
C11 N2 C2 C3 -175.9(16) . . . . ?
N2 C2 C3 N1 1(2) . . . . ?
C1 N1 C3 C2 0(2) . . . . ?
C4 N1 C3 C2 174.1(14) . . . . ?
C1 N1 C4 C5 -132.8(14) . . . . ?
C3 N1 C4 C5 54.2(18) . . . . ?
N1 C4 C5 C10 -125.5(12) . . . . ?
N1 C4 C5 C6 56.2(16) . . . . ?
C10 C5 C6 C7 -1(2) . . . . ?
C4 C5 C6 C7 177.6(13) . . . . ?
C5 C6 C7 C8 1(2) . . . . ?
C6 C7 C8 C9 -1(3) . . . . ?
C22 O1 C9 C10 -3(2) . . . . ?
C22 O1 C9 C8 174.9(16) . . . . ?
C7 C8 C9 C10 1(3) . . . . ?
C7 C8 C9 O1 -177.1(13) . . . . ?
O1 C9 C10 C5 176.7(13) . . . . ?
C8 C9 C10 C5 -1(2) . . . . ?
C6 C5 C10 C9 0.9(19) . . . . ?
C4 C5 C10 C9 -177.4(12) . . . . ?
C16 C12 C13 C14 -3.3(13) . . . . ?
C17 C12 C13 C14 173.9(12) . . . . ?
Ir1 C12 C13 C14 -64.5(9) . . . . ?
C16 C12 C13 C18 -172.3(11) . . . . ?
C17 C12 C13 C18 5(2) . . . . ?
Ir1 C12 C13 C18 126.5(12) . . . . ?
C16 C12 C13 Ir1 61.2(8) . . . . ?
C17 C12 C13 Ir1 -121.5(13) . . . . ?
C12 C13 C14 C15 1.9(14) . . . . ?
C18 C13 C14 C15 171.1(11) . . . . ?
Ir1 C13 C14 C15 -60.2(9) . . . . ?
C12 C13 C14 C19 -177.4(12) . . . . ?
C18 C13 C14 C19 -8(2) . . . . ?
Ir1 C13 C14 C19 120.5(14) . . . . ?
C12 C13 C14 Ir1 62.1(8) . . . . ?
C18 C13 C14 Ir1 -128.7(12) . . . . ?
C13 C14 C15 C16 0.3(14) . . . . ?
C19 C14 C15 C16 179.5(13) . . . . ?
Ir1 C14 C15 C16 -57.5(8) . . . . ?
C13 C14 C15 C20 -178.2(12) . . . . ?
C19 C14 C15 C20 1(2) . . . . ?
Ir1 C14 C15 C20 124.0(13) . . . . ?
C13 C14 C15 Ir1 57.8(9) . . . . ?
C19 C14 C15 Ir1 -123.0(15) . . . . ?
C13 C12 C16 C15 3.4(13) . . . . ?
C17 C12 C16 C15 -173.8(12) . . . . ?
Ir1 C12 C16 C15 64.4(8) . . . . ?
C13 C12 C16 C21 174.8(12) . . . . ?
C17 C12 C16 C21 -2(2) . . . . ?
Ir1 C12 C16 C21 -124.3(13) . . . . ?
C13 C12 C16 Ir1 -61.0(8) . . . . ?
C17 C12 C16 Ir1 121.8(13) . . . . ?
C14 C15 C16 C12 -2.3(14) . . . . ?
C20 C15 C16 C12 176.3(11) . . . . ?
Ir1 C15 C16 C12 -62.2(8) . . . . ?
C14 C15 C16 C21 -174.0(12) . . . . ?
C20 C15 C16 C21 4.7(18) . . . . ?
Ir1 C15 C16 C21 126.1(12) . . . . ?
C14 C15 C16 Ir1 59.9(9) . . . . ?
C20 C15 C16 Ir1 -121.4(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11C Cl2 0.98 2.67 3.391(17) 131.0 . yes
C4 H4B Cl1 0.99 2.43 3.253(13) 139.9 . yes
C4 H4A Cl1 0.99 2.59 3.578(13) 173.1 2 yes

_refine_diff_density_max         2.707
_refine_diff_density_min         -1.876
_refine_diff_density_rms         0.181




