# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ga_210507da_a
_database_code_depnum_ccdc_archive 'CCDC 2093357'
loop_
_audit_author_name
_audit_author_address
'Zi-Jian Yao'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2021-06-30 deposited with the CCDC.	2021-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 Br0.30 Cl0.70 Ir N3'
_chemical_formula_weight         558.41

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'
Br Br -0.9338 1.0006 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.9625(14)
_cell_length_b                   15.3150(13)
_cell_length_c                   8.0607(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.794(4)
_cell_angle_gamma                90
_cell_volume                     1960.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      56.86

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_F_000             1074
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    9.809
_shelx_estimated_absorpt_T_min   0.140
_shelx_estimated_absorpt_T_max   0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            28794
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.845
_diffrn_reflns_theta_max         57.033
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4007
_reflns_number_gt                3256
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0294P)²+3.4360P] 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         4007
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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 0.77913(2) 0.50755(2) 0.51733(2) 0.02767(9) Uani 1 1 d . . . . .
Cl1 Cl 0.87455(7) 0.52498(6) 0.29565(12) 0.0384(4) Uani 0.704(5) 1 d . . P . .
Br1 Br 0.87455(7) 0.52498(6) 0.29565(12) 0.0384(4) Uani 0.296(5) 1 d . . P . .
N1 N 0.7742(3) 0.6964(3) 0.5486(5) 0.0273(9) Uani 1 1 d . . . . .
N2 N 0.8821(3) 0.6581(3) 0.7103(5) 0.0334(10) Uani 1 1 d . . . . .
N3 N 0.4758(4) 0.6067(4) -0.0702(7) 0.0611(16) Uani 1 1 d . . . . .
C1 C 0.6964(3) 0.5910(3) 0.3855(6) 0.0277(11) Uani 1 1 d . . . . .
C2 C 0.6345(3) 0.5725(3) 0.2589(6) 0.0302(11) Uani 1 1 d . . . . .
H2 H 0.6259 0.5138 0.2232 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5838(3) 0.6386(3) 0.1815(6) 0.0327(12) Uani 1 1 d . . . . .
C4 C 0.5935(4) 0.7256(4) 0.2301(6) 0.0350(12) Uani 1 1 d . . . . .
H4 H 0.5575 0.7695 0.1793 0.042 Uiso 1 1 calc R U . . .
C5 C 0.6567(4) 0.7468(3) 0.3538(6) 0.0337(12) Uani 1 1 d . . . . .
H5 H 0.6661 0.8057 0.3877 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7056(3) 0.6805(3) 0.4263(6) 0.0282(11) Uani 1 1 d . . . . .
C7 C 0.8179(3) 0.6256(3) 0.6069(6) 0.0298(11) Uani 1 1 d . . . . .
C8 C 0.8774(4) 0.7481(3) 0.7130(7) 0.0373(13) Uani 1 1 d . . . . .
H8 H 0.9155 0.7860 0.7762 0.045 Uiso 1 1 calc R U . . .
C9 C 0.8107(4) 0.7726(3) 0.6122(6) 0.0341(12) Uani 1 1 d . . . . .
H9 H 0.7919 0.8306 0.5887 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5225(4) 0.6190(4) 0.0428(8) 0.0419(14) Uani 1 1 d . . . . .
C11 C 0.9481(4) 0.6080(4) 0.8023(8) 0.0467(15) Uani 1 1 d . . . . .
H11A H 0.9316 0.5943 0.9132 0.070 Uiso 1 1 calc R U . . .
H11B H 1.0003 0.6422 0.8137 0.070 Uiso 1 1 calc R U . . .
H11C H 0.9572 0.5537 0.7424 0.070 Uiso 1 1 calc R U . . .
C12 C 0.8163(4) 0.4103(4) 0.7229(7) 0.0448(16) Uani 1 1 d . . . . .
C13 C 0.7301(4) 0.4402(4) 0.7230(7) 0.0425(15) Uani 1 1 d . . . . .
C14 C 0.6845(4) 0.4088(3) 0.5688(7) 0.0375(13) Uani 1 1 d . . . . .
C15 C 0.7434(4) 0.3680(3) 0.4720(7) 0.0369(13) Uani 1 1 d . . . . .
C16 C 0.8247(4) 0.3701(3) 0.5701(8) 0.0412(14) Uani 1 1 d . . . . .
C17 C 0.8811(6) 0.4104(5) 0.8715(9) 0.074(3) Uani 1 1 d . . . . .
H17A H 0.8767 0.3562 0.9347 0.111 Uiso 1 1 calc R U . . .
H17B H 0.8714 0.4604 0.9430 0.111 Uiso 1 1 calc R U . . .
H17C H 0.9374 0.4147 0.8340 0.111 Uiso 1 1 calc R U . . .
C18 C 0.6917(6) 0.4796(5) 0.8657(9) 0.070(2) Uani 1 1 d . . . . .
H18A H 0.6725 0.4332 0.9364 0.104 Uiso 1 1 calc R U . . .
H18B H 0.6437 0.5160 0.8237 0.104 Uiso 1 1 calc R U . . .
H18C H 0.7337 0.5157 0.9311 0.104 Uiso 1 1 calc R U . . .
C19 C 0.5911(4) 0.4145(5) 0.5288(9) 0.0602(19) Uani 1 1 d . . . . .
H19A H 0.5772 0.4130 0.4076 0.090 Uiso 1 1 calc R U . . .
H19B H 0.5706 0.4691 0.5733 0.090 Uiso 1 1 calc R U . . .
H19C H 0.5642 0.3649 0.5794 0.090 Uiso 1 1 calc R U . . .
C20 C 0.7237(5) 0.3242(4) 0.3071(8) 0.0580(19) Uani 1 1 d . . . . .
H20A H 0.7217 0.2609 0.3231 0.087 Uiso 1 1 calc R U . . .
H20B H 0.7674 0.3385 0.2344 0.087 Uiso 1 1 calc R U . . .
H20C H 0.6689 0.3446 0.2555 0.087 Uiso 1 1 calc R U . . .
C21 C 0.9047(5) 0.3328(4) 0.5193(10) 0.066(2) Uani 1 1 d . . . . .
H21A H 0.9516 0.3719 0.5556 0.099 Uiso 1 1 calc R U . . .
H21B H 0.9003 0.3266 0.3977 0.099 Uiso 1 1 calc R U . . .
H21C H 0.9148 0.2754 0.5713 0.099 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 C7 2.020(5) . ?
Ir1 C1 2.055(5) . ?
Ir1 C13 2.165(5) . ?
Ir1 C14 2.207(6) . ?
Ir1 C15 2.232(5) . ?
Ir1 C16 2.253(5) . ?
Ir1 C12 2.263(5) . ?
Ir1 Cl1 2.4765(10) . ?
N1 C7 1.347(6) . ?
N1 C9 1.380(6) . ?
N1 C6 1.418(7) . ?
N2 C7 1.350(7) . ?
N2 C8 1.381(7) . ?
N2 C11 1.446(7) . ?
N3 C10 1.132(8) . ?
C1 C2 1.377(7) . ?
C1 C6 1.414(7) . ?
C2 C3 1.402(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(8) . ?
C3 C10 1.442(8) . ?
C4 C5 1.383(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(7) . ?
C5 H5 0.9500 . ?
C8 C9 1.328(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C16 1.395(8) . ?
C12 C13 1.451(9) . ?
C12 C17 1.501(9) . ?
C13 C14 1.457(8) . ?
C13 C18 1.485(9) . ?
C14 C15 1.425(8) . ?
C14 C19 1.496(9) . ?
C15 C16 1.450(8) . ?
C15 C20 1.494(8) . ?
C16 C21 1.494(9) . ?
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 . ?

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
C7 Ir1 C1 77.6(2) . . ?
C7 Ir1 C13 105.9(2) . . ?
C1 Ir1 C13 115.4(2) . . ?
C7 Ir1 C14 137.5(2) . . ?
C1 Ir1 C14 96.2(2) . . ?
C13 Ir1 C14 38.9(2) . . ?
C7 Ir1 C15 168.23(19) . . ?
C1 Ir1 C15 111.76(19) . . ?
C13 Ir1 C15 64.1(2) . . ?
C14 Ir1 C15 37.4(2) . . ?
C7 Ir1 C16 133.4(2) . . ?
C1 Ir1 C16 149.0(2) . . ?
C13 Ir1 C16 62.9(2) . . ?
C14 Ir1 C16 62.5(2) . . ?
C15 Ir1 C16 37.7(2) . . ?
C7 Ir1 C12 106.21(19) . . ?
C1 Ir1 C12 153.6(2) . . ?
C13 Ir1 C12 38.2(2) . . ?
C14 Ir1 C12 62.9(2) . . ?
C15 Ir1 C12 62.18(19) . . ?
C16 Ir1 C12 36.0(2) . . ?
C7 Ir1 Cl1 88.47(15) . . ?
C1 Ir1 Cl1 88.26(14) . . ?
C13 Ir1 Cl1 154.17(17) . . ?
C14 Ir1 Cl1 133.80(16) . . ?
C15 Ir1 Cl1 98.67(16) . . ?
C16 Ir1 Cl1 91.54(17) . . ?
C12 Ir1 Cl1 117.68(19) . . ?
C7 N1 C9 111.6(4) . . ?
C7 N1 C6 116.1(4) . . ?
C9 N1 C6 132.0(4) . . ?
C7 N2 C8 109.8(4) . . ?
C7 N2 C11 126.2(5) . . ?
C8 N2 C11 124.0(5) . . ?
C2 C1 C6 115.0(5) . . ?
C2 C1 Ir1 129.1(4) . . ?
C6 C1 Ir1 115.9(4) . . ?
C1 C2 C3 121.3(5) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 121.5(5) . . ?
C4 C3 C10 117.7(5) . . ?
C2 C3 C10 120.7(5) . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C6 C5 C4 118.3(5) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C1 125.1(5) . . ?
C5 C6 N1 122.3(5) . . ?
C1 C6 N1 112.5(4) . . ?
N1 C7 N2 104.6(4) . . ?
N1 C7 Ir1 117.8(4) . . ?
N2 C7 Ir1 137.5(4) . . ?
C9 C8 N2 108.3(5) . . ?
C9 C8 H8 125.9 . . ?
N2 C8 H8 125.9 . . ?
C8 C9 N1 105.7(5) . . ?
C8 C9 H9 127.2 . . ?
N1 C9 H9 127.2 . . ?
N3 C10 C3 176.7(6) . . ?
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 108.4(5) . . ?
C16 C12 C17 125.9(7) . . ?
C13 C12 C17 125.2(7) . . ?
C16 C12 Ir1 71.6(3) . . ?
C13 C12 Ir1 67.3(3) . . ?
C17 C12 Ir1 133.8(4) . . ?
C12 C13 C14 106.7(5) . . ?
C12 C13 C18 126.5(6) . . ?
C14 C13 C18 125.8(7) . . ?
C12 C13 Ir1 74.6(3) . . ?
C14 C13 Ir1 72.1(3) . . ?
C18 C13 Ir1 127.5(4) . . ?
C15 C14 C13 108.1(5) . . ?
C15 C14 C19 127.3(6) . . ?
C13 C14 C19 124.5(6) . . ?
C15 C14 Ir1 72.2(3) . . ?
C13 C14 Ir1 69.0(3) . . ?
C19 C14 Ir1 127.3(4) . . ?
C14 C15 C16 107.2(5) . . ?
C14 C15 C20 126.3(6) . . ?
C16 C15 C20 126.3(6) . . ?
C14 C15 Ir1 70.3(3) . . ?
C16 C15 Ir1 71.9(3) . . ?
C20 C15 Ir1 127.1(4) . . ?
C12 C16 C15 109.3(6) . . ?
C12 C16 C21 124.8(6) . . ?
C15 C16 C21 125.8(6) . . ?
C12 C16 Ir1 72.4(3) . . ?
C15 C16 Ir1 70.4(3) . . ?
C21 C16 Ir1 125.0(4) . . ?
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 . . ?

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
C6 C1 C2 C3 -1.6(8) . . . . ?
Ir1 C1 C2 C3 -179.5(4) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C1 C2 C3 C10 176.4(5) . . . . ?
C2 C3 C4 C5 2.2(8) . . . . ?
C10 C3 C4 C5 -174.8(5) . . . . ?
C3 C4 C5 C6 -1.7(8) . . . . ?
C4 C5 C6 C1 -0.4(8) . . . . ?
C4 C5 C6 N1 177.1(5) . . . . ?
C2 C1 C6 C5 2.1(8) . . . . ?
Ir1 C1 C6 C5 -179.7(4) . . . . ?
C2 C1 C6 N1 -175.6(5) . . . . ?
Ir1 C1 C6 N1 2.6(6) . . . . ?
C7 N1 C6 C5 -178.7(5) . . . . ?
C9 N1 C6 C5 -5.0(9) . . . . ?
C7 N1 C6 C1 -1.0(6) . . . . ?
C9 N1 C6 C1 172.8(5) . . . . ?
C9 N1 C7 N2 0.7(6) . . . . ?
C6 N1 C7 N2 175.7(4) . . . . ?
C9 N1 C7 Ir1 -176.2(3) . . . . ?
C6 N1 C7 Ir1 -1.1(6) . . . . ?
C8 N2 C7 N1 -0.4(6) . . . . ?
C11 N2 C7 N1 -178.9(5) . . . . ?
C8 N2 C7 Ir1 175.4(4) . . . . ?
C11 N2 C7 Ir1 -3.0(9) . . . . ?
C7 N2 C8 C9 0.0(7) . . . . ?
C11 N2 C8 C9 178.5(6) . . . . ?
N2 C8 C9 N1 0.4(6) . . . . ?
C7 N1 C9 C8 -0.7(6) . . . . ?
C6 N1 C9 C8 -174.7(5) . . . . ?
C16 C12 C13 C14 5.4(6) . . . . ?
C17 C12 C13 C14 -166.1(5) . . . . ?
Ir1 C12 C13 C14 65.4(3) . . . . ?
C16 C12 C13 C18 174.4(6) . . . . ?
C17 C12 C13 C18 3.0(9) . . . . ?
Ir1 C12 C13 C18 -125.5(6) . . . . ?
C16 C12 C13 Ir1 -60.1(4) . . . . ?
C17 C12 C13 Ir1 128.5(6) . . . . ?
C12 C13 C14 C15 -5.1(6) . . . . ?
C18 C13 C14 C15 -174.3(5) . . . . ?
Ir1 C13 C14 C15 62.0(4) . . . . ?
C12 C13 C14 C19 171.3(5) . . . . ?
C18 C13 C14 C19 2.2(9) . . . . ?
Ir1 C13 C14 C19 -121.6(5) . . . . ?
C12 C13 C14 Ir1 -67.1(4) . . . . ?
C18 C13 C14 Ir1 123.8(6) . . . . ?
C13 C14 C15 C16 3.0(6) . . . . ?
C19 C14 C15 C16 -173.3(5) . . . . ?
Ir1 C14 C15 C16 62.9(4) . . . . ?
C13 C14 C15 C20 178.0(5) . . . . ?
C19 C14 C15 C20 1.6(9) . . . . ?
Ir1 C14 C15 C20 -122.1(6) . . . . ?
C13 C14 C15 Ir1 -59.9(4) . . . . ?
C19 C14 C15 Ir1 123.8(6) . . . . ?
C13 C12 C16 C15 -3.6(6) . . . . ?
C17 C12 C16 C15 167.8(6) . . . . ?
Ir1 C12 C16 C15 -61.0(4) . . . . ?
C13 C12 C16 C21 178.2(5) . . . . ?
C17 C12 C16 C21 -10.4(10) . . . . ?
Ir1 C12 C16 C21 120.8(6) . . . . ?
C13 C12 C16 Ir1 57.4(4) . . . . ?
C17 C12 C16 Ir1 -131.3(6) . . . . ?
C14 C15 C16 C12 0.4(6) . . . . ?
C20 C15 C16 C12 -174.6(5) . . . . ?
Ir1 C15 C16 C12 62.2(4) . . . . ?
C14 C15 C16 C21 178.5(6) . . . . ?
C20 C15 C16 C21 3.6(9) . . . . ?
Ir1 C15 C16 C21 -119.6(6) . . . . ?
C14 C15 C16 Ir1 -61.9(4) . . . . ?
C20 C15 C16 Ir1 123.2(6) . . . . ?

_refine_diff_density_max         0.955
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.138

####################################################################### 
# 
# 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_210507b_c
_database_code_depnum_ccdc_archive 'CCDC 2093356'
loop_
_audit_author_name
_audit_author_address
'Zi-Jian Yao'
;Shanghai Institute of Technology
China
;
_audit_update_record             
;
2021-09-02 deposited with the CCDC.	2021-09-09 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            'C20 H24 Cl0.35 I0.65 Ir N2'
_chemical_formula_weight         579.50

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'
I I 0.0030 5.4350 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.6569(8)
_cell_length_b                   8.7972(5)
_cell_length_c                   16.3348(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.717(2)
_cell_angle_gamma                90
_cell_volume                     1914.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      56.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_F_000             1102
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    14.925
_shelx_estimated_absorpt_T_min   0.247
_shelx_estimated_absorpt_T_max   0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.216
_exptl_absorpt_correction_T_max  0.370
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            26774
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.829
_diffrn_reflns_theta_max         56.980
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3894
_reflns_number_gt                3503
_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)+(0.0235P)²+2.7157P] 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         3894
_refine_ls_number_parameters     232
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0611
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_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 0.22805(2) 0.68718(2) 0.37018(2) 0.02857(7) Uani 1 1 d D . . . .
Cl1 Cl 0.2041(10) 0.4872(11) 0.4642(9) 0.067(3) Uani 0.35 1 d D U P . .
I1 I 0.19270(10) 0.44938(16) 0.46160(9) 0.0382(2) Uani 0.65 1 d D U P . .
N1 N 0.4403(3) 0.6239(5) 0.3988(3) 0.0446(10) Uani 1 1 d . . . . .
N2 N 0.4248(3) 0.7587(5) 0.5049(3) 0.0506(11) Uani 1 1 d . . . . .
C1 C 0.2981(4) 0.5424(5) 0.3031(3) 0.0399(10) Uani 1 1 d . . . . .
C2 C 0.2550(5) 0.4486(6) 0.2353(3) 0.0543(14) Uani 1 1 d . . . . .
H2 H 0.183954 0.445468 0.217164 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3130(7) 0.3603(7) 0.1938(4) 0.075(2) Uani 1 1 d . . . . .
H3 H 0.281680 0.298467 0.147739 0.090 Uiso 1 1 calc R U . . .
C4 C 0.4158(7) 0.3625(8) 0.2196(4) 0.085(3) Uani 1 1 d . . . . .
H4 H 0.455141 0.302605 0.190599 0.102 Uiso 1 1 calc R U . . .
C5 C 0.4628(5) 0.4501(7) 0.2867(4) 0.072(2) Uani 1 1 d . . . . .
H5 H 0.533841 0.451557 0.304577 0.087 Uiso 1 1 calc R U . . .
C6 C 0.4027(4) 0.5360(5) 0.3274(3) 0.0449(11) Uani 1 1 d . . . . .
C7 C 0.3711(3) 0.6970(5) 0.4326(3) 0.0364(10) Uani 1 1 d . . . . .
C8 C 0.5254(4) 0.7247(7) 0.5157(4) 0.0631(17) Uani 1 1 d . . . . .
H8 H 0.577511 0.755535 0.561335 0.076 Uiso 1 1 calc R U . . .
C9 C 0.5362(4) 0.6406(7) 0.4503(4) 0.0654(18) Uani 1 1 d . . . . .
H9 H 0.597116 0.599961 0.440644 0.078 Uiso 1 1 calc R U . . .
C10 C 0.3827(5) 0.8447(7) 0.5645(3) 0.0705(18) Uani 1 1 d . . . . .
H10A H 0.385749 0.953476 0.552323 0.106 Uiso 1 1 calc R U . . .
H10B H 0.421289 0.824350 0.621490 0.106 Uiso 1 1 calc R U . . .
H10C H 0.312676 0.814509 0.559981 0.106 Uiso 1 1 calc R U . . .
C11 C 0.1674(4) 0.8386(6) 0.2678(3) 0.0514(13) Uani 1 1 d . . . . .
C12 C 0.0863(4) 0.7492(6) 0.2802(4) 0.0626(17) Uani 1 1 d . . . . .
C13 C 0.0728(4) 0.7826(7) 0.3624(5) 0.0671(19) Uani 1 1 d . . . . .
C14 C 0.1430(4) 0.8927(6) 0.3984(3) 0.0533(14) Uani 1 1 d . . . . .
C15 C 0.2012(4) 0.9267(5) 0.3402(3) 0.0472(12) Uani 1 1 d . . . . .
C16 C 0.2039(7) 0.8494(9) 0.1862(4) 0.098(3) Uani 1 1 d . U . . .
H16A H 0.202758 0.748220 0.160965 0.147 Uiso 1 1 calc R U . . .
H16B H 0.272572 0.889271 0.198021 0.147 Uiso 1 1 calc R U . . .
H16C H 0.159779 0.917749 0.147242 0.147 Uiso 1 1 calc R U . . .
C17 C 0.0173(6) 0.6526(9) 0.2171(6) 0.123(4) Uani 1 1 d . U . . .
H17A H -0.004538 0.564798 0.245338 0.184 Uiso 1 1 calc R U . . .
H17B H 0.052793 0.617370 0.174586 0.184 Uiso 1 1 calc R U . . .
H17C H -0.041375 0.712588 0.189971 0.184 Uiso 1 1 calc R U . . .
C18 C -0.0069(6) 0.7187(10) 0.4028(7) 0.117(3) Uani 1 1 d . U . . .
H18A H -0.066823 0.783005 0.389034 0.175 Uiso 1 1 calc R U . . .
H18B H 0.018076 0.715785 0.463767 0.175 Uiso 1 1 calc R U . . .
H18C H -0.023895 0.615429 0.381843 0.175 Uiso 1 1 calc R U . . .
C19 C 0.1421(7) 0.9776(10) 0.4792(4) 0.113(3) Uani 1 1 d . U . . .
H19A H 0.208455 1.021943 0.501367 0.169 Uiso 1 1 calc R U . . .
H19B H 0.125509 0.906892 0.520496 0.169 Uiso 1 1 calc R U . . .
H19C H 0.091733 1.058687 0.467842 0.169 Uiso 1 1 calc R U . . .
C20 C 0.2821(5) 1.0461(7) 0.3515(5) 0.092(3) Uani 1 1 d . U . . .
H20A H 0.254937 1.138909 0.321786 0.137 Uiso 1 1 calc R U . . .
H20B H 0.338261 1.008782 0.328814 0.137 Uiso 1 1 calc R U . . .
H20C H 0.305597 1.068465 0.411434 0.137 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 C7 1.996(4) . ?
Ir1 C1 2.049(4) . ?
Ir1 C11 2.156(5) . ?
Ir1 C15 2.176(5) . ?
Ir1 C12 2.226(5) . ?
Ir1 C14 2.251(5) . ?
Ir1 C13 2.257(5) . ?
Ir1 Cl1 2.404(11) . ?
Ir1 I1 2.6753(14) . ?
N1 C7 1.358(6) . ?
N1 C6 1.399(7) . ?
N1 C9 1.401(6) . ?
N2 C7 1.359(6) . ?
N2 C8 1.379(7) . ?
N2 C10 1.448(8) . ?
C1 C6 1.398(7) . ?
C1 C2 1.403(7) . ?
C2 C3 1.388(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(7) . ?
C5 H5 0.9500 . ?
C8 C9 1.333(9) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C15 1.404(7) . ?
C11 C12 1.409(8) . ?
C11 C16 1.525(8) . ?
C12 C13 1.424(9) . ?
C12 C17 1.498(8) . ?
C13 C14 1.398(9) . ?
C13 C18 1.501(9) . ?
C14 C15 1.400(8) . ?
C14 C19 1.518(8) . ?
C15 C20 1.506(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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 . ?

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
C7 Ir1 C1 77.33(19) . . ?
C7 Ir1 C11 122.4(2) . . ?
C1 Ir1 C11 96.56(18) . . ?
C7 Ir1 C15 99.80(17) . . ?
C1 Ir1 C15 123.8(2) . . ?
C11 Ir1 C15 37.82(19) . . ?
C7 Ir1 C12 159.7(2) . . ?
C1 Ir1 C12 103.9(2) . . ?
C11 Ir1 C12 37.5(2) . . ?
C15 Ir1 C12 62.30(18) . . ?
C7 Ir1 C14 110.6(2) . . ?
C1 Ir1 C14 158.67(18) . . ?
C11 Ir1 C14 62.30(18) . . ?
C15 Ir1 C14 36.8(2) . . ?
C12 Ir1 C14 61.7(2) . . ?
C7 Ir1 C13 144.5(2) . . ?
C1 Ir1 C13 138.1(3) . . ?
C11 Ir1 C13 62.0(2) . . ?
C15 Ir1 C13 61.2(2) . . ?
C12 Ir1 C13 37.0(2) . . ?
C14 Ir1 C13 36.1(2) . . ?
C7 Ir1 Cl1 87.8(3) . . ?
C1 Ir1 Cl1 91.8(3) . . ?
C11 Ir1 Cl1 149.8(4) . . ?
C15 Ir1 Cl1 144.4(3) . . ?
C12 Ir1 Cl1 112.4(4) . . ?
C14 Ir1 Cl1 107.9(4) . . ?
C13 Ir1 Cl1 92.9(4) . . ?
C7 Ir1 I1 91.45(12) . . ?
C1 Ir1 I1 88.59(13) . . ?
C11 Ir1 I1 146.14(17) . . ?
C15 Ir1 I1 147.22(15) . . ?
C12 Ir1 I1 108.83(18) . . ?
C14 Ir1 I1 110.42(16) . . ?
C13 Ir1 I1 92.28(15) . . ?
Cl1 Ir1 I1 5.6(3) . . ?
C7 N1 C6 116.1(4) . . ?
C7 N1 C9 110.4(5) . . ?
C6 N1 C9 133.0(5) . . ?
C7 N2 C8 110.9(5) . . ?
C7 N2 C10 125.1(4) . . ?
C8 N2 C10 124.0(5) . . ?
C6 C1 C2 115.2(5) . . ?
C6 C1 Ir1 116.2(3) . . ?
C2 C1 Ir1 128.6(4) . . ?
C3 C2 C1 122.0(6) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C4 C3 C2 119.8(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.1(6) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 117.7(6) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C5 C6 C1 124.2(6) . . ?
C5 C6 N1 123.6(5) . . ?
C1 C6 N1 112.2(4) . . ?
N1 C7 N2 104.6(4) . . ?
N1 C7 Ir1 117.6(3) . . ?
N2 C7 Ir1 137.9(4) . . ?
C9 C8 N2 107.5(5) . . ?
C9 C8 H8 126.2 . . ?
N2 C8 H8 126.2 . . ?
C8 C9 N1 106.6(5) . . ?
C8 C9 H9 126.7 . . ?
N1 C9 H9 126.7 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C11 C12 108.1(5) . . ?
C15 C11 C16 126.2(6) . . ?
C12 C11 C16 125.4(6) . . ?
C15 C11 Ir1 71.8(3) . . ?
C12 C11 Ir1 74.0(3) . . ?
C16 C11 Ir1 124.9(4) . . ?
C11 C12 C13 106.8(5) . . ?
C11 C12 C17 127.8(7) . . ?
C13 C12 C17 125.0(7) . . ?
C11 C12 Ir1 68.6(3) . . ?
C13 C12 Ir1 72.7(3) . . ?
C17 C12 Ir1 129.7(4) . . ?
C14 C13 C12 108.8(5) . . ?
C14 C13 C18 124.8(7) . . ?
C12 C13 C18 126.4(7) . . ?
C14 C13 Ir1 71.7(3) . . ?
C12 C13 Ir1 70.3(3) . . ?
C18 C13 Ir1 126.8(4) . . ?
C13 C14 C15 107.5(5) . . ?
C13 C14 C19 124.8(7) . . ?
C15 C14 C19 126.8(6) . . ?
C13 C14 Ir1 72.2(3) . . ?
C15 C14 Ir1 68.7(3) . . ?
C19 C14 Ir1 132.6(4) . . ?
C14 C15 C11 108.9(5) . . ?
C14 C15 C20 125.2(6) . . ?
C11 C15 C20 125.8(6) . . ?
C14 C15 Ir1 74.5(3) . . ?
C11 C15 Ir1 70.3(3) . . ?
C20 C15 Ir1 124.4(4) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 . . ?

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
C6 C1 C2 C3 -2.2(7) . . . . ?
Ir1 C1 C2 C3 177.5(4) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C5 0.6(9) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
C4 C5 C6 C1 -1.8(8) . . . . ?
C4 C5 C6 N1 176.7(5) . . . . ?
C2 C1 C6 C5 2.9(7) . . . . ?
Ir1 C1 C6 C5 -176.8(4) . . . . ?
C2 C1 C6 N1 -175.9(4) . . . . ?
Ir1 C1 C6 N1 4.4(5) . . . . ?
C7 N1 C6 C5 -177.8(4) . . . . ?
C9 N1 C6 C5 -6.3(8) . . . . ?
C7 N1 C6 C1 0.9(6) . . . . ?
C9 N1 C6 C1 172.4(5) . . . . ?
C6 N1 C7 N2 173.4(4) . . . . ?
C9 N1 C7 N2 0.1(5) . . . . ?
C6 N1 C7 Ir1 -6.1(5) . . . . ?
C9 N1 C7 Ir1 -179.5(3) . . . . ?
C8 N2 C7 N1 0.1(5) . . . . ?
C10 N2 C7 N1 -178.1(5) . . . . ?
C8 N2 C7 Ir1 179.5(4) . . . . ?
C10 N2 C7 Ir1 1.3(8) . . . . ?
C7 N2 C8 C9 -0.2(6) . . . . ?
C10 N2 C8 C9 178.0(5) . . . . ?
N2 C8 C9 N1 0.2(6) . . . . ?
C7 N1 C9 C8 -0.2(6) . . . . ?
C6 N1 C9 C8 -172.0(5) . . . . ?
C15 C11 C12 C13 -1.1(5) . . . . ?
C16 C11 C12 C13 -175.2(5) . . . . ?
Ir1 C11 C12 C13 63.1(4) . . . . ?
C15 C11 C12 C17 171.4(6) . . . . ?
C16 C11 C12 C17 -2.6(9) . . . . ?
Ir1 C11 C12 C17 -124.4(6) . . . . ?
C15 C11 C12 Ir1 -64.2(3) . . . . ?
C16 C11 C12 Ir1 121.7(5) . . . . ?
C11 C12 C13 C14 1.3(6) . . . . ?
C17 C12 C13 C14 -171.5(5) . . . . ?
Ir1 C12 C13 C14 61.7(4) . . . . ?
C11 C12 C13 C18 177.8(5) . . . . ?
C17 C12 C13 C18 5.0(9) . . . . ?
Ir1 C12 C13 C18 -121.7(6) . . . . ?
C11 C12 C13 Ir1 -60.4(3) . . . . ?
C17 C12 C13 Ir1 126.8(6) . . . . ?
C12 C13 C14 C15 -1.0(6) . . . . ?
C18 C13 C14 C15 -177.6(5) . . . . ?
Ir1 C13 C14 C15 59.9(3) . . . . ?
C12 C13 C14 C19 169.2(5) . . . . ?
C18 C13 C14 C19 -7.4(9) . . . . ?
Ir1 C13 C14 C19 -129.9(5) . . . . ?
C12 C13 C14 Ir1 -60.8(4) . . . . ?
C18 C13 C14 Ir1 122.6(6) . . . . ?
C13 C14 C15 C11 0.3(5) . . . . ?
C19 C14 C15 C11 -169.7(5) . . . . ?
Ir1 C14 C15 C11 62.4(3) . . . . ?
C13 C14 C15 C20 176.4(5) . . . . ?
C19 C14 C15 C20 6.4(8) . . . . ?
Ir1 C14 C15 C20 -121.5(5) . . . . ?
C13 C14 C15 Ir1 -62.1(3) . . . . ?
C19 C14 C15 Ir1 127.9(5) . . . . ?
C12 C11 C15 C14 0.6(5) . . . . ?
C16 C11 C15 C14 174.5(5) . . . . ?
Ir1 C11 C15 C14 -65.0(3) . . . . ?
C12 C11 C15 C20 -175.5(5) . . . . ?
C16 C11 C15 C20 -1.6(8) . . . . ?
Ir1 C11 C15 C20 118.9(5) . . . . ?
C12 C11 C15 Ir1 65.6(3) . . . . ?
C16 C11 C15 Ir1 -120.4(5) . . . . ?

_refine_diff_density_max         0.867
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.101

