# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_Ir1
_database_code_depnum_ccdc_archive 'CCDC 2365892'
loop_
_audit_author_name
_audit_author_address
'Loi Do'
;University of Houston
United States of America
;
_audit_update_record             
;
2024-06-26 deposited with the CCDC.	2024-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C22 H24 Cl Ir N2 O, 0.364(C2 H8 O2), C H2 Cl2, 0.272(C H4 O)'
_chemical_formula_sum            'C24 H30 Cl3 Ir N2 O2'
_chemical_formula_weight         677.05

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'
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'
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'

_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                   7.8001(3)
_cell_length_b                   23.1587(10)
_cell_length_c                   14.2754(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.122(2)
_cell_angle_gamma                90
_cell_volume                     2564.00(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    5.543
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.5026
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   EMPIRICAL
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            33456
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.683
_diffrn_reflns_theta_max         25.061
_diffrn_reflns_theta_full        25.061
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4546
_reflns_number_gt                4219
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0197P)²+8.2628P] 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         4546
_refine_ls_number_parameters     299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0547
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.004
_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 0.30436(2) 0.64362(2) 0.52606(2) 0.01393(6) Uani 1 1 d . . . . .
Cl1 Cl 0.57196(11) 0.61425(4) 0.47021(6) 0.02054(19) Uani 1 1 d . . . . .
O1 O 0.6492(3) 0.74550(12) 0.70010(18) 0.0243(6) Uani 1 1 d . . . . .
N1 N 0.3757(4) 0.72697(13) 0.4881(2) 0.0143(6) Uani 1 1 d . . . . .
C1 C 0.4871(5) 0.64236(16) 0.7311(3) 0.0186(8) Uani 1 1 d . . . . .
Cl2 Cl 0.9400(2) 0.89715(6) 0.66576(9) 0.0519(3) Uani 1 1 d . . . . .
N2 N 0.4555(4) 0.67433(13) 0.6458(2) 0.0170(6) Uani 1 1 d . . . . .
C2 C 0.4308(5) 0.66349(19) 0.8141(3) 0.0248(9) Uani 1 1 d . . . . .
H2 H 0.371992 0.699415 0.813923 0.030 Uiso 1 1 calc R U . . .
Cl3 Cl 1.16824(16) 0.79747(6) 0.69169(11) 0.0564(4) Uani 1 1 d . . . . .
C3 C 0.4609(6) 0.6321(2) 0.8968(3) 0.0334(10) Uani 1 1 d . . . . .
H3 H 0.422294 0.646494 0.953172 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5464(6) 0.5801(2) 0.8977(3) 0.0397(12) Uani 1 1 d . . . . .
H4 H 0.566629 0.558629 0.954578 0.048 Uiso 1 1 calc R U . . .
C5 C 0.6029(6) 0.5590(2) 0.8153(3) 0.0371(11) Uani 1 1 d . . . . .
H5 H 0.662548 0.523239 0.815895 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5727(5) 0.58991(17) 0.7325(3) 0.0250(9) Uani 1 1 d . . . . .
H6 H 0.610837 0.575126 0.676219 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5407(5) 0.72392(16) 0.6402(2) 0.0173(8) Uani 1 1 d . . . . .
C8 C 0.4911(4) 0.75447(16) 0.5492(2) 0.0164(7) Uani 1 1 d . . . . .
C9 C 0.5553(5) 0.80809(17) 0.5296(3) 0.0266(9) Uani 1 1 d . . . . .
H9 H 0.637263 0.826573 0.573668 0.032 Uiso 1 1 calc R U . . .
C10 C 0.4993(5) 0.83474(19) 0.4450(3) 0.0311(10) Uani 1 1 d . . . . .
H10 H 0.543120 0.871463 0.429889 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3790(5) 0.80703(17) 0.3833(3) 0.0233(9) Uani 1 1 d . . . . .
H11 H 0.336028 0.824933 0.325704 0.028 Uiso 1 1 calc R U . . .
C12 C 0.3213(5) 0.75304(17) 0.4059(3) 0.0191(8) Uani 1 1 d . . . . .
H12 H 0.240724 0.733640 0.362206 0.023 Uiso 1 1 calc R U . . .
C13 C 0.1696(4) 0.56793(17) 0.4646(3) 0.0196(8) Uani 1 1 d . . . . .
C14 C 0.1659(5) 0.56790(17) 0.5651(3) 0.0198(8) Uani 1 1 d . . . . .
C15 C 0.0748(5) 0.61969(18) 0.5877(3) 0.0237(9) Uani 1 1 d . . . . .
C16 C 0.0284(5) 0.65108(16) 0.5025(3) 0.0233(9) Uani 1 1 d . . . . .
C17 C 0.0867(5) 0.61843(17) 0.4258(3) 0.0228(8) Uani 1 1 d . . . . .
C18 C 0.2481(5) 0.52139(18) 0.4099(3) 0.0267(9) Uani 1 1 d . . . . .
H18A H 0.158948 0.493470 0.387006 0.040 Uiso 1 1 calc R U . . .
H18B H 0.338748 0.501704 0.450841 0.040 Uiso 1 1 calc R U . . .
H18C H 0.297998 0.538563 0.356261 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2271(5) 0.51983(18) 0.6306(3) 0.0293(10) Uani 1 1 d . . . . .
H19A H 0.136761 0.490413 0.630359 0.044 Uiso 1 1 calc R U . . .
H19B H 0.253507 0.535116 0.694479 0.044 Uiso 1 1 calc R U . . .
H19C H 0.331148 0.502515 0.609610 0.044 Uiso 1 1 calc R U . . .
C20 C 0.0269(6) 0.6353(2) 0.6834(3) 0.0358(11) Uani 1 1 d . . . . .
H20A H 0.026376 0.677444 0.690134 0.054 Uiso 1 1 calc R U . . .
H20B H 0.111081 0.618641 0.731807 0.054 Uiso 1 1 calc R U . . .
H20C H -0.088076 0.620131 0.690970 0.054 Uiso 1 1 calc R U . . .
C21 C -0.0701(5) 0.70709(18) 0.4923(4) 0.0354(11) Uani 1 1 d . . . . .
H21A H -0.018612 0.732179 0.447596 0.053 Uiso 1 1 calc R U . . .
H21B H -0.065121 0.726297 0.553688 0.053 Uiso 1 1 calc R U . . .
H21C H -0.190551 0.699229 0.468948 0.053 Uiso 1 1 calc R U . . .
C22 C 0.0472(6) 0.6312(2) 0.3228(3) 0.0340(10) Uani 1 1 d . . . . .
H22A H 0.139615 0.615846 0.288491 0.051 Uiso 1 1 calc R U . . .
H22B H 0.038733 0.673068 0.313370 0.051 Uiso 1 1 calc R U . . .
H22C H -0.062397 0.613054 0.299120 0.051 Uiso 1 1 calc R U . . .
C40 C 0.9875(6) 0.83263(19) 0.7291(3) 0.0318(10) Uani 1 1 d . . . . .
H40A H 1.010007 0.841585 0.797125 0.038 Uiso 1 1 calc R U . . .
H40B H 0.886568 0.806530 0.720260 0.038 Uiso 1 1 calc R U . . .
C50A C 0.1775(13) 0.5066(4) 0.8983(7) 0.0774(19) Uani 0.728(6) 1 d D . P A 1
H50A H 0.154058 0.468602 0.869556 0.116 Uiso 0.728(6) 1 calc R U P A 1
H50B H 0.301099 0.510229 0.918437 0.116 Uiso 0.728(6) 1 calc R U P A 1
H50C H 0.142201 0.536814 0.852126 0.116 Uiso 0.728(6) 1 calc R U P A 1
O50A O 0.0808(9) 0.5129(2) 0.9798(5) 0.0774(19) Uani 0.728(6) 1 d D . P A 1
H60A H 0.087361 0.482092 1.011158 0.116 Uiso 0.728(6) 1 calc R U P A 1
C50B C 0.082(3) 0.4998(11) 0.871(2) 0.0774(19) Uani 0.272(6) 1 d D . P A 2
H50D H 0.000854 0.532205 0.862554 0.116 Uiso 0.272(6) 1 calc R U P A 2
H50E H 0.094351 0.482221 0.809591 0.116 Uiso 0.272(6) 1 calc R U P A 2
H50F H 0.194181 0.513759 0.899122 0.116 Uiso 0.272(6) 1 calc R U P A 2
O50B O 0.022(2) 0.4604(7) 0.9277(14) 0.0774(19) Uani 0.272(6) 1 d D . P A 2
H60B H 0.093906 0.433646 0.937777 0.116 Uiso 0.272(6) 1 calc R U P A 2


_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 N2 2.095(3) . ?
Ir1 N1 2.096(3) . ?
Ir1 C16 2.150(4) . ?
Ir1 C15 2.150(4) . ?
Ir1 C14 2.164(4) . ?
Ir1 C13 2.180(4) . ?
Ir1 C17 2.180(4) . ?
Ir1 Cl1 2.4105(9) . ?
O1 C7 1.242(4) . ?
N1 C8 1.345(5) . ?
N1 C12 1.347(5) . ?
C1 C6 1.385(5) . ?
C1 C2 1.395(5) . ?
C1 N2 1.424(5) . ?
Cl2 C40 1.765(5) . ?
N2 C7 1.334(5) . ?
C2 C3 1.385(6) . ?
Cl3 C40 1.760(5) . ?
C3 C4 1.376(7) . ?
C4 C5 1.388(7) . ?
C5 C6 1.380(6) . ?
C7 C8 1.494(5) . ?
C8 C9 1.379(5) . ?
C9 C10 1.384(6) . ?
C10 C11 1.375(6) . ?
C11 C12 1.379(5) . ?
C13 C17 1.420(6) . ?
C13 C14 1.439(5) . ?
C13 C18 1.499(5) . ?
C14 C15 1.448(6) . ?
C14 C19 1.498(6) . ?
C15 C16 1.431(6) . ?
C15 C20 1.499(6) . ?
C16 C17 1.443(6) . ?
C16 C21 1.506(6) . ?
C17 C22 1.500(6) . ?
C50A O50A 1.460(10) . ?
O50A O50A 1.559(12) 3_567 ?
C50B O50B 1.338(17) . ?

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
N2 Ir1 N1 75.90(11) . . ?
N2 Ir1 C16 124.58(14) . . ?
N1 Ir1 C16 100.05(13) . . ?
N2 Ir1 C15 100.03(13) . . ?
N1 Ir1 C15 126.79(14) . . ?
C16 Ir1 C15 38.87(16) . . ?
N2 Ir1 C14 108.53(13) . . ?
N1 Ir1 C14 165.15(13) . . ?
C16 Ir1 C14 65.57(15) . . ?
C15 Ir1 C14 39.21(15) . . ?
N2 Ir1 C13 143.80(13) . . ?
N1 Ir1 C13 140.03(13) . . ?
C16 Ir1 C13 64.52(14) . . ?
C15 Ir1 C13 64.58(14) . . ?
C14 Ir1 C13 38.69(14) . . ?
N2 Ir1 C17 163.27(14) . . ?
N1 Ir1 C17 106.65(13) . . ?
C16 Ir1 C17 38.93(15) . . ?
C15 Ir1 C17 64.89(15) . . ?
C14 Ir1 C17 64.98(14) . . ?
C13 Ir1 C17 38.01(14) . . ?
N2 Ir1 Cl1 86.20(9) . . ?
N1 Ir1 Cl1 84.90(8) . . ?
C16 Ir1 Cl1 149.18(12) . . ?
C15 Ir1 Cl1 148.31(12) . . ?
C14 Ir1 Cl1 109.29(10) . . ?
C13 Ir1 Cl1 92.14(10) . . ?
C17 Ir1 Cl1 110.40(11) . . ?
C8 N1 C12 118.7(3) . . ?
C8 N1 Ir1 116.5(2) . . ?
C12 N1 Ir1 124.8(2) . . ?
C6 C1 C2 119.3(4) . . ?
C6 C1 N2 120.5(3) . . ?
C2 C1 N2 120.2(3) . . ?
C7 N2 C1 117.2(3) . . ?
C7 N2 Ir1 119.0(2) . . ?
C1 N2 Ir1 123.5(2) . . ?
C3 C2 C1 119.9(4) . . ?
C4 C3 C2 120.4(4) . . ?
C3 C4 C5 119.7(4) . . ?
C6 C5 C4 120.2(4) . . ?
C5 C6 C1 120.3(4) . . ?
O1 C7 N2 127.8(3) . . ?
O1 C7 C8 120.2(3) . . ?
N2 C7 C8 112.0(3) . . ?
N1 C8 C9 121.8(3) . . ?
N1 C8 C7 115.7(3) . . ?
C9 C8 C7 122.5(3) . . ?
C8 C9 C10 119.4(4) . . ?
C11 C10 C9 118.7(4) . . ?
C10 C11 C12 119.4(4) . . ?
N1 C12 C11 122.0(3) . . ?
C17 C13 C14 109.4(3) . . ?
C17 C13 C18 125.7(4) . . ?
C14 C13 C18 124.9(4) . . ?
C17 C13 Ir1 71.0(2) . . ?
C14 C13 Ir1 70.1(2) . . ?
C18 C13 Ir1 125.5(3) . . ?
C13 C14 C15 106.5(3) . . ?
C13 C14 C19 125.7(4) . . ?
C15 C14 C19 127.5(4) . . ?
C13 C14 Ir1 71.3(2) . . ?
C15 C14 Ir1 69.9(2) . . ?
C19 C14 Ir1 128.9(3) . . ?
C16 C15 C14 108.5(3) . . ?
C16 C15 C20 126.0(4) . . ?
C14 C15 C20 125.4(4) . . ?
C16 C15 Ir1 70.6(2) . . ?
C14 C15 Ir1 70.9(2) . . ?
C20 C15 Ir1 127.6(3) . . ?
C15 C16 C17 107.9(3) . . ?
C15 C16 C21 126.9(4) . . ?
C17 C16 C21 125.2(4) . . ?
C15 C16 Ir1 70.6(2) . . ?
C17 C16 Ir1 71.7(2) . . ?
C21 C16 Ir1 125.2(3) . . ?
C13 C17 C16 107.7(3) . . ?
C13 C17 C22 125.6(4) . . ?
C16 C17 C22 126.3(4) . . ?
C13 C17 Ir1 71.0(2) . . ?
C16 C17 Ir1 69.4(2) . . ?
C22 C17 Ir1 130.9(3) . . ?
Cl3 C40 Cl2 111.5(2) . . ?
C50A O50A O50A 139.8(10) . 3_567 ?

_refine_diff_density_max         1.775
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_Ir3
_database_code_depnum_ccdc_archive 'CCDC 2365894'
loop_
_audit_author_name
_audit_author_address
'Loi Do'
;University of Houston
United States of America
;
_audit_update_record             
;
2024-06-26 deposited with the CCDC.	2024-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H36 Cl Ir N2 O'
_chemical_formula_weight         644.24

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'
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'
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'

_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                   14.2282(4)
_cell_length_b                   12.0061(4)
_cell_length_c                   15.7691(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.675(2)
_cell_angle_gamma                90
_cell_volume                     2580.48(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4928
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.09

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    5.300
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6112
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            14851
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.167
_diffrn_reflns_theta_max         25.149
_diffrn_reflns_theta_full        25.149
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4603
_reflns_number_gt                3888
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0217P)²+0.9369P] 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         4603
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0543
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.002
_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 0.62430(2) 0.36505(2) 0.32943(2) 0.01228(6) Uani 1 1 d . . . . .
Cl1 Cl 0.57958(8) 0.33947(10) 0.17213(7) 0.0245(3) Uani 1 1 d . . . . .
O1 O 0.71955(19) 0.4878(2) 0.30649(18) 0.0161(6) Uani 1 1 d . . . . .
N1 N 0.7499(2) 0.2732(3) 0.3288(2) 0.0142(7) Uani 1 1 d . . . . .
N2 N 0.8632(2) 0.5084(3) 0.2650(2) 0.0174(8) Uani 1 1 d . . . . .
C1 C 0.7624(3) 0.1643(3) 0.3446(3) 0.0163(9) Uani 1 1 d . . . . .
H1 H 0.713833 0.124037 0.362531 0.020 Uiso 1 1 calc R U . . .
C2 C 0.8435(3) 0.1087(4) 0.3359(3) 0.0213(10) Uani 1 1 d . . . . .
H2 H 0.851359 0.031373 0.348765 0.026 Uiso 1 1 calc R U . . .
C4 C 0.9009(3) 0.2781(4) 0.2923(3) 0.0199(10) Uani 1 1 d . . . . .
H4 H 0.948383 0.319648 0.273863 0.024 Uiso 1 1 calc R U . . .
C3 C 0.9136(3) 0.1659(4) 0.3082(3) 0.0240(11) Uani 1 1 d . . . . .
H3 H 0.969344 0.128489 0.300406 0.029 Uiso 1 1 calc R U . . .
C5 C 0.8186(3) 0.3300(3) 0.3032(3) 0.0153(9) Uani 1 1 d . . . . .
C6 C 0.7986(3) 0.4515(3) 0.2895(2) 0.0128(9) Uani 1 1 d . . . . .
C7 C 0.8528(3) 0.6243(3) 0.2503(3) 0.0151(9) Uani 1 1 d . . . . .
C8 C 0.8038(3) 0.6647(3) 0.1646(3) 0.0172(9) Uani 1 1 d . . . . .
C9 C 0.8034(3) 0.7779(3) 0.1499(3) 0.0186(9) Uani 1 1 d . . . . .
H9 H 0.770800 0.805813 0.092642 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8491(3) 0.8521(3) 0.2162(3) 0.0203(10) Uani 1 1 d . . . . .
H10 H 0.846302 0.929878 0.204874 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8988(3) 0.8116(4) 0.2992(3) 0.0205(10) Uani 1 1 d . . . . .
H11 H 0.930633 0.862384 0.344542 0.025 Uiso 1 1 calc R U . . .
C12 C 0.9031(3) 0.6987(4) 0.3174(3) 0.0173(9) Uani 1 1 d . . . . .
C13 C 0.9617(3) 0.6526(4) 0.4065(3) 0.0248(11) Uani 1 1 d . . . . .
H13 H 0.986904 0.577823 0.395560 0.030 Uiso 1 1 calc R U . . .
C14 C 1.0509(3) 0.7246(5) 0.4521(3) 0.0401(13) Uani 1 1 d . . . . .
H14A H 1.091980 0.685126 0.503977 0.060 Uiso 1 1 calc R U . . .
H14B H 1.028690 0.795232 0.470885 0.060 Uiso 1 1 calc R U . . .
H14C H 1.089193 0.739499 0.410629 0.060 Uiso 1 1 calc R U . . .
C15 C 0.8988(4) 0.6354(4) 0.4685(3) 0.0345(12) Uani 1 1 d . . . . .
H15A H 0.874612 0.707631 0.482353 0.052 Uiso 1 1 calc R U . . .
H15B H 0.938138 0.600241 0.523278 0.052 Uiso 1 1 calc R U . . .
H15C H 0.843026 0.587374 0.439959 0.052 Uiso 1 1 calc R U . . .
C16 C 0.7570(3) 0.5815(4) 0.0917(3) 0.0207(10) Uani 1 1 d . . . . .
H16 H 0.722570 0.524037 0.117734 0.025 Uiso 1 1 calc R U . . .
C17 C 0.8363(3) 0.5218(4) 0.0605(3) 0.0281(11) Uani 1 1 d . . . . .
H17A H 0.882992 0.485862 0.111211 0.042 Uiso 1 1 calc R U . . .
H17B H 0.871052 0.575999 0.034072 0.042 Uiso 1 1 calc R U . . .
H17C H 0.805717 0.465252 0.016425 0.042 Uiso 1 1 calc R U . . .
C18 C 0.6804(3) 0.6348(4) 0.0129(3) 0.0294(11) Uani 1 1 d . . . . .
H18A H 0.632686 0.676583 0.034414 0.044 Uiso 1 1 calc R U . . .
H18B H 0.646448 0.576369 -0.027872 0.044 Uiso 1 1 calc R U . . .
H18C H 0.713278 0.685503 -0.018211 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5641(3) 0.4661(3) 0.4146(3) 0.0167(9) Uani 1 1 d . . . . .
C20 C 0.4867(3) 0.4270(3) 0.3402(3) 0.0153(9) Uani 1 1 d . . . . .
C21 C 0.4859(3) 0.3065(4) 0.3433(3) 0.0168(9) Uani 1 1 d . . . . .
C22 C 0.5625(3) 0.2723(3) 0.4185(3) 0.0174(9) Uani 1 1 d . . . . .
C23 C 0.6133(3) 0.3705(3) 0.4626(3) 0.0182(9) Uani 1 1 d . . . . .
C24 C 0.5917(3) 0.5843(4) 0.4378(3) 0.0229(10) Uani 1 1 d . . . . .
H24A H 0.657946 0.598021 0.433060 0.034 Uiso 1 1 calc R U . . .
H24B H 0.590391 0.598961 0.498572 0.034 Uiso 1 1 calc R U . . .
H24C H 0.545084 0.633667 0.397022 0.034 Uiso 1 1 calc R U . . .
C25 C 0.4140(3) 0.4953(4) 0.2731(3) 0.0216(10) Uani 1 1 d . . . . .
H25A H 0.433275 0.573909 0.280298 0.032 Uiso 1 1 calc R U . . .
H25B H 0.348844 0.486398 0.281552 0.032 Uiso 1 1 calc R U . . .
H25C H 0.412363 0.470437 0.213514 0.032 Uiso 1 1 calc R U . . .
C26 C 0.4143(3) 0.2338(4) 0.2789(3) 0.0245(10) Uani 1 1 d . . . . .
H26A H 0.348552 0.244947 0.285532 0.037 Uiso 1 1 calc R U . . .
H26B H 0.433479 0.155632 0.290590 0.037 Uiso 1 1 calc R U . . .
H26C H 0.414062 0.253226 0.218508 0.037 Uiso 1 1 calc R U . . .
C28 C 0.6935(3) 0.3731(4) 0.5480(3) 0.0283(11) Uani 1 1 d . . . . .
H28A H 0.664881 0.372581 0.597602 0.042 Uiso 1 1 calc R U . . .
H28B H 0.732757 0.440771 0.550662 0.042 Uiso 1 1 calc R U . . .
H28C H 0.735589 0.307517 0.551798 0.042 Uiso 1 1 calc R U . . .
C27 C 0.5830(3) 0.1554(3) 0.4510(3) 0.0257(11) Uani 1 1 d . . . . .
H27A H 0.546786 0.139159 0.493845 0.038 Uiso 1 1 calc R U . . .
H27B H 0.653493 0.146546 0.479507 0.038 Uiso 1 1 calc R U . . .
H27C H 0.562251 0.103831 0.400910 0.038 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 N1 2.103(3) . ?
Ir1 O1 2.103(3) . ?
Ir1 C20 2.147(4) . ?
Ir1 C23 2.151(4) . ?
Ir1 C19 2.161(4) . ?
Ir1 C21 2.161(4) . ?
Ir1 C22 2.168(4) . ?
Ir1 Cl1 2.3971(10) . ?
O1 C6 1.304(4) . ?
N1 C1 1.333(5) . ?
N1 C5 1.345(5) . ?
N2 C6 1.290(5) . ?
N2 C7 1.411(5) . ?
C1 C2 1.375(5) . ?
C2 C3 1.380(6) . ?
C4 C3 1.372(6) . ?
C4 C5 1.380(5) . ?
C5 C6 1.491(6) . ?
C7 C12 1.413(6) . ?
C7 C8 1.417(6) . ?
C8 C9 1.378(6) . ?
C8 C16 1.524(6) . ?
C9 C10 1.385(6) . ?
C10 C11 1.385(6) . ?
C11 C12 1.383(6) . ?
C12 C13 1.517(6) . ?
C13 C15 1.517(6) . ?
C13 C14 1.535(6) . ?
C16 C17 1.532(6) . ?
C16 C18 1.538(6) . ?
C19 C20 1.438(6) . ?
C19 C23 1.441(6) . ?
C19 C24 1.490(6) . ?
C20 C21 1.448(6) . ?
C20 C25 1.494(5) . ?
C21 C22 1.422(6) . ?
C21 C26 1.495(6) . ?
C22 C23 1.453(6) . ?
C22 C27 1.493(6) . ?
C23 C28 1.496(6) . ?

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
N1 Ir1 O1 77.08(11) . . ?
N1 Ir1 C20 168.00(14) . . ?
O1 Ir1 C20 114.72(13) . . ?
N1 Ir1 C23 108.73(14) . . ?
O1 Ir1 C23 112.18(13) . . ?
C20 Ir1 C23 65.70(15) . . ?
N1 Ir1 C19 141.89(14) . . ?
O1 Ir1 C19 95.94(13) . . ?
C20 Ir1 C19 39.00(15) . . ?
C23 Ir1 C19 39.03(15) . . ?
N1 Ir1 C21 129.09(15) . . ?
O1 Ir1 C21 153.72(13) . . ?
C20 Ir1 C21 39.29(15) . . ?
C23 Ir1 C21 65.62(15) . . ?
C19 Ir1 C21 65.43(15) . . ?
N1 Ir1 C22 103.73(14) . . ?
O1 Ir1 C22 150.84(13) . . ?
C20 Ir1 C22 65.02(15) . . ?
C23 Ir1 C22 39.30(15) . . ?
C19 Ir1 C22 65.07(15) . . ?
C21 Ir1 C22 38.36(15) . . ?
N1 Ir1 Cl1 84.33(9) . . ?
O1 Ir1 Cl1 84.53(8) . . ?
C20 Ir1 Cl1 98.56(11) . . ?
C23 Ir1 Cl1 160.38(11) . . ?
C19 Ir1 Cl1 132.85(11) . . ?
C21 Ir1 Cl1 94.82(11) . . ?
C22 Ir1 Cl1 124.63(11) . . ?
C6 O1 Ir1 115.9(2) . . ?
C1 N1 C5 119.0(3) . . ?
C1 N1 Ir1 125.5(3) . . ?
C5 N1 Ir1 115.3(3) . . ?
C6 N2 C7 121.4(3) . . ?
N1 C1 C2 121.9(4) . . ?
C1 C2 C3 119.6(4) . . ?
C3 C4 C5 119.5(4) . . ?
C4 C3 C2 118.5(4) . . ?
N1 C5 C4 121.6(4) . . ?
N1 C5 C6 114.5(3) . . ?
C4 C5 C6 123.9(4) . . ?
N2 C6 O1 128.0(4) . . ?
N2 C6 C5 116.0(3) . . ?
O1 C6 C5 116.0(3) . . ?
N2 C7 C12 119.6(4) . . ?
N2 C7 C8 119.6(4) . . ?
C12 C7 C8 120.2(4) . . ?
C9 C8 C7 118.4(4) . . ?
C9 C8 C16 122.6(4) . . ?
C7 C8 C16 118.9(4) . . ?
C8 C9 C10 121.9(4) . . ?
C11 C10 C9 119.3(4) . . ?
C12 C11 C10 121.4(4) . . ?
C11 C12 C7 118.8(4) . . ?
C11 C12 C13 122.0(4) . . ?
C7 C12 C13 119.2(4) . . ?
C15 C13 C12 112.2(4) . . ?
C15 C13 C14 109.6(4) . . ?
C12 C13 C14 112.9(4) . . ?
C8 C16 C17 110.3(3) . . ?
C8 C16 C18 113.0(4) . . ?
C17 C16 C18 110.6(4) . . ?
C20 C19 C23 108.2(4) . . ?
C20 C19 C24 126.7(4) . . ?
C23 C19 C24 125.1(4) . . ?
C20 C19 Ir1 70.0(2) . . ?
C23 C19 Ir1 70.1(2) . . ?
C24 C19 Ir1 124.3(3) . . ?
C19 C20 C21 108.1(4) . . ?
C19 C20 C25 127.7(4) . . ?
C21 C20 C25 124.2(4) . . ?
C19 C20 Ir1 71.0(2) . . ?
C21 C20 Ir1 70.9(2) . . ?
C25 C20 Ir1 126.6(3) . . ?
C22 C21 C20 107.8(4) . . ?
C22 C21 C26 127.4(4) . . ?
C20 C21 C26 124.8(4) . . ?
C22 C21 Ir1 71.1(2) . . ?
C20 C21 Ir1 69.8(2) . . ?
C26 C21 Ir1 125.7(3) . . ?
C21 C22 C23 108.8(4) . . ?
C21 C22 C27 125.8(4) . . ?
C23 C22 C27 125.3(4) . . ?
C21 C22 Ir1 70.6(2) . . ?
C23 C22 Ir1 69.7(2) . . ?
C27 C22 Ir1 129.0(3) . . ?
C19 C23 C22 107.2(3) . . ?
C19 C23 C28 126.0(4) . . ?
C22 C23 C28 126.4(4) . . ?
C19 C23 Ir1 70.8(2) . . ?
C22 C23 Ir1 71.0(2) . . ?
C28 C23 Ir1 129.0(3) . . ?

_refine_diff_density_max         1.173
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_Ir2
_database_code_depnum_ccdc_archive 'CCDC 2365893'
loop_
_audit_author_name
_audit_author_address
'Loi Do'
;University of Houston
United States of America
;
_audit_update_record             
;
2024-06-26 deposited with the CCDC.	2024-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 Cl Ir N2 O'
_chemical_formula_sum            'C24 H28 Cl Ir N2 O'
_chemical_formula_weight         588.13

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   16.0992(3)
_cell_length_b                   9.4204(2)
_cell_length_c                   30.4486(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4617.86(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9764
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.10

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    5.915
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.4682
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   EMPIRICAL
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            51458
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.841
_diffrn_reflns_theta_max         25.156
_diffrn_reflns_theta_full        25.156
_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             4129
_reflns_number_gt                3815
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _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-2019/2 (Sheldrick, 2019)'
_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)+(0.0119P)²+11.2364P] 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         4129
_refine_ls_number_parameters     263
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0173
_refine_ls_wR_factor_ref         0.0384
_refine_ls_wR_factor_gt          0.0375
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.076
_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
O1 O 0.47780(13) 0.1804(2) 0.46593(7) 0.0225(4) Uani 1 1 d . U . . .
N1 N 0.49511(14) 0.2896(2) 0.39889(7) 0.0128(5) Uani 1 1 d . . . . .
C1 C 0.58390(17) 0.2825(3) 0.40253(9) 0.0139(6) Uani 1 1 d . . . . .
N2 N 0.34307(14) 0.3807(2) 0.39787(8) 0.0130(5) Uani 1 1 d . . . . .
C2 C 0.62940(18) 0.1840(3) 0.37772(9) 0.0157(6) Uani 1 1 d . . . . .
C3 C 0.71595(18) 0.1875(3) 0.38054(10) 0.0199(7) Uani 1 1 d . . . . .
H3 H 0.747746 0.121618 0.363930 0.024 Uiso 1 1 calc R U . . .
C4 C 0.75623(19) 0.2845(3) 0.40693(10) 0.0206(7) Uani 1 1 d . . . . .
H4 H 0.815197 0.286531 0.407846 0.025 Uiso 1 1 calc R U . . .
C5 C 0.71073(18) 0.3786(3) 0.43202(10) 0.0187(6) Uani 1 1 d . . . . .
H5 H 0.738806 0.444418 0.450416 0.022 Uiso 1 1 calc R U . . .
C6 C 0.62418(18) 0.3784(3) 0.43075(9) 0.0158(6) Uani 1 1 d . . . . .
C7 C 0.5865(2) 0.0750(3) 0.34979(10) 0.0207(7) Uani 1 1 d . . . . .
H7A H 0.547055 0.021347 0.367829 0.031 Uiso 1 1 calc R U . . .
H7B H 0.627794 0.010043 0.337369 0.031 Uiso 1 1 calc R U . . .
H7C H 0.556566 0.122631 0.325934 0.031 Uiso 1 1 calc R U . . .
C8 C 0.57636(19) 0.4770(3) 0.46013(10) 0.0221(7) Uani 1 1 d . . . . .
H8A H 0.524680 0.505231 0.445542 0.033 Uiso 1 1 calc R U . . .
H8B H 0.609909 0.561499 0.466246 0.033 Uiso 1 1 calc R U . . .
H8C H 0.563304 0.428531 0.487759 0.033 Uiso 1 1 calc R U . . .
Ir1 Ir 0.43158(2) 0.38659(2) 0.34728(2) 0.00974(4) Uani 1 1 d . . . . .
Cl1 Cl 0.37461(4) 0.15399(7) 0.33054(2) 0.01871(15) Uani 1 1 d . . . . .
C9 C 0.4515(2) 0.2483(3) 0.43362(10) 0.0225(4) Uani 1 1 d . U . . .
C10 C 0.36351(18) 0.2997(3) 0.43288(9) 0.0143(6) Uani 1 1 d . . . . .
C11 C 0.30809(18) 0.2740(3) 0.46668(10) 0.0188(6) Uani 1 1 d . . . . .
H11 H 0.323425 0.214569 0.490555 0.023 Uiso 1 1 calc R U . . .
C12 C 0.23008(19) 0.3356(3) 0.46535(10) 0.0209(7) Uani 1 1 d . . . . .
H12 H 0.191370 0.320298 0.488421 0.025 Uiso 1 1 calc R U . . .
C13 C 0.20963(19) 0.4199(3) 0.42976(10) 0.0199(6) Uani 1 1 d . . . . .
H13 H 0.156816 0.464617 0.428310 0.024 Uiso 1 1 calc R U . . .
C14 C 0.26674(17) 0.4385(3) 0.39630(10) 0.0158(6) Uani 1 1 d . . . . .
H14 H 0.251580 0.493773 0.371459 0.019 Uiso 1 1 calc R U . . .
C15 C 0.41431(18) 0.6025(3) 0.32467(9) 0.0140(6) Uani 1 1 d . . . . .
C16 C 0.38890(18) 0.5066(3) 0.29076(9) 0.0140(6) Uani 1 1 d . . . . .
C17 C 0.46153(18) 0.4252(3) 0.27849(9) 0.0147(6) Uani 1 1 d . . . . .
C18 C 0.52962(17) 0.4687(3) 0.30476(9) 0.0146(6) Uani 1 1 d . . . . .
C19 C 0.50056(18) 0.5781(3) 0.33451(9) 0.0141(6) Uani 1 1 d . . . . .
C20 C 0.3633(2) 0.7159(3) 0.34562(10) 0.0219(7) Uani 1 1 d . . . . .
H20A H 0.304341 0.697664 0.339987 0.033 Uiso 1 1 calc R U . . .
H20B H 0.378699 0.808306 0.333284 0.033 Uiso 1 1 calc R U . . .
H20C H 0.373387 0.716213 0.377360 0.033 Uiso 1 1 calc R U . . .
C21 C 0.30550(18) 0.4986(4) 0.26894(10) 0.0220(7) Uani 1 1 d . . . . .
H21A H 0.292037 0.399267 0.262574 0.033 Uiso 1 1 calc R U . . .
H21B H 0.306767 0.552801 0.241470 0.033 Uiso 1 1 calc R U . . .
H21C H 0.263211 0.538570 0.288509 0.033 Uiso 1 1 calc R U . . .
C22 C 0.4650(2) 0.3155(3) 0.24310(10) 0.0247(7) Uani 1 1 d . . . . .
H22A H 0.504554 0.241120 0.251370 0.037 Uiso 1 1 calc R U . . .
H22B H 0.482884 0.359827 0.215561 0.037 Uiso 1 1 calc R U . . .
H22C H 0.409764 0.273613 0.239146 0.037 Uiso 1 1 calc R U . . .
C23 C 0.61830(19) 0.4248(4) 0.29900(11) 0.0259(7) Uani 1 1 d . . . . .
H23A H 0.646984 0.429685 0.327354 0.039 Uiso 1 1 calc R U . . .
H23B H 0.645525 0.488681 0.278072 0.039 Uiso 1 1 calc R U . . .
H23C H 0.620471 0.327332 0.287818 0.039 Uiso 1 1 calc R U . . .
C24 C 0.5543(2) 0.6637(3) 0.36451(11) 0.0249(7) Uani 1 1 d . . . . .
H24A H 0.519736 0.708945 0.387007 0.037 Uiso 1 1 calc R U . . .
H24B H 0.583321 0.736867 0.347542 0.037 Uiso 1 1 calc R U . . .
H24C H 0.595059 0.601429 0.378656 0.037 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
O1 C9 1.248(4) . ?
N1 C9 1.328(4) . ?
N1 C1 1.435(4) . ?
N1 Ir1 2.086(2) . ?
C1 C2 1.403(4) . ?
C1 C6 1.405(4) . ?
N2 C14 1.345(4) . ?
N2 C10 1.352(4) . ?
N2 Ir1 2.099(2) . ?
C2 C3 1.397(4) . ?
C2 C7 1.501(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9500 . ?
C6 C8 1.502(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
Ir1 C19 2.154(3) . ?
Ir1 C15 2.166(3) . ?
Ir1 C16 2.171(3) . ?
Ir1 C17 2.180(3) . ?
Ir1 C18 2.183(3) . ?
Ir1 Cl1 2.4294(7) . ?
C9 C10 1.497(4) . ?
C10 C11 1.383(4) . ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.432(4) . ?
C15 C19 1.439(4) . ?
C15 C20 1.490(4) . ?
C16 C17 1.447(4) . ?
C16 C21 1.500(4) . ?
C17 C18 1.417(4) . ?
C17 C22 1.494(4) . ?
C18 C19 1.450(4) . ?
C18 C23 1.497(4) . ?
C19 C24 1.494(4) . ?
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 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C9 N1 C1 116.8(2) . . ?
C9 N1 Ir1 117.96(19) . . ?
C1 N1 Ir1 124.56(17) . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 N1 120.6(3) . . ?
C6 C1 N1 118.5(2) . . ?
C14 N2 C10 118.6(2) . . ?
C14 N2 Ir1 125.70(19) . . ?
C10 N2 Ir1 115.36(18) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C7 120.7(3) . . ?
C1 C2 C7 121.1(3) . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C8 119.7(3) . . ?
C1 C6 C8 121.7(3) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 Ir1 N2 76.62(9) . . ?
N1 Ir1 C19 104.48(10) . . ?
N2 Ir1 C19 120.29(10) . . ?
N1 Ir1 C15 135.56(10) . . ?
N2 Ir1 C15 99.84(10) . . ?
C19 Ir1 C15 38.92(10) . . ?
N1 Ir1 C16 168.72(10) . . ?
N2 Ir1 C16 112.37(10) . . ?
C19 Ir1 C16 65.41(10) . . ?
C15 Ir1 C16 38.57(11) . . ?
N1 Ir1 C17 133.52(10) . . ?
N2 Ir1 C17 149.27(10) . . ?
C19 Ir1 C17 64.71(11) . . ?
C15 Ir1 C17 64.28(11) . . ?
C16 Ir1 C17 38.86(10) . . ?
N1 Ir1 C18 104.32(10) . . ?
N2 Ir1 C18 159.28(10) . . ?
C19 Ir1 C18 39.06(11) . . ?
C15 Ir1 C18 64.63(10) . . ?
C16 Ir1 C18 64.80(10) . . ?
C17 Ir1 C18 37.92(11) . . ?
N1 Ir1 Cl1 87.03(7) . . ?
N2 Ir1 Cl1 82.76(6) . . ?
C19 Ir1 Cl1 155.82(8) . . ?
C15 Ir1 Cl1 137.06(8) . . ?
C16 Ir1 Cl1 100.59(8) . . ?
C17 Ir1 Cl1 91.86(8) . . ?
C18 Ir1 Cl1 117.90(8) . . ?
O1 C9 N1 126.8(3) . . ?
O1 C9 C10 119.9(3) . . ?
N1 C9 C10 113.2(2) . . ?
N2 C10 C11 121.9(3) . . ?
N2 C10 C9 115.1(2) . . ?
C11 C10 C9 122.8(3) . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 118.7(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
N2 C14 C13 122.0(3) . . ?
N2 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C16 C15 C19 109.0(2) . . ?
C16 C15 C20 127.1(3) . . ?
C19 C15 C20 123.8(3) . . ?
C16 C15 Ir1 70.91(16) . . ?
C19 C15 Ir1 70.10(15) . . ?
C20 C15 Ir1 127.4(2) . . ?
C15 C16 C17 106.8(2) . . ?
C15 C16 C21 127.4(3) . . ?
C17 C16 C21 125.6(3) . . ?
C15 C16 Ir1 70.52(15) . . ?
C17 C16 Ir1 70.91(15) . . ?
C21 C16 Ir1 127.5(2) . . ?
C18 C17 C16 109.0(2) . . ?
C18 C17 C22 125.3(3) . . ?
C16 C17 C22 125.6(3) . . ?
C18 C17 Ir1 71.15(16) . . ?
C16 C17 Ir1 70.23(15) . . ?
C22 C17 Ir1 125.9(2) . . ?
C17 C18 C19 108.0(2) . . ?
C17 C18 C23 126.3(3) . . ?
C19 C18 C23 125.3(3) . . ?
C17 C18 Ir1 70.93(16) . . ?
C19 C18 Ir1 69.40(15) . . ?
C23 C18 Ir1 131.4(2) . . ?
C15 C19 C18 107.1(2) . . ?
C15 C19 C24 126.8(3) . . ?
C18 C19 C24 125.4(3) . . ?
C15 C19 Ir1 70.98(15) . . ?
C18 C19 Ir1 71.55(15) . . ?
C24 C19 Ir1 129.8(2) . . ?
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 . . ?
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 . . ?

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
C9 N1 C1 C2 111.5(3) . . . . ?
Ir1 N1 C1 C2 -77.9(3) . . . . ?
C9 N1 C1 C6 -69.9(3) . . . . ?
Ir1 N1 C1 C6 100.7(3) . . . . ?
C6 C1 C2 C3 -2.4(4) . . . . ?
N1 C1 C2 C3 176.2(3) . . . . ?
C6 C1 C2 C7 176.0(3) . . . . ?
N1 C1 C2 C7 -5.5(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C7 C2 C3 C4 -178.3(3) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 -1.5(4) . . . . ?
C4 C5 C6 C8 176.9(3) . . . . ?
C2 C1 C6 C5 3.1(4) . . . . ?
N1 C1 C6 C5 -175.5(2) . . . . ?
C2 C1 C6 C8 -175.3(3) . . . . ?
N1 C1 C6 C8 6.1(4) . . . . ?
C1 N1 C9 O1 -14.0(5) . . . . ?
Ir1 N1 C9 O1 174.7(3) . . . . ?
C1 N1 C9 C10 162.2(2) . . . . ?
Ir1 N1 C9 C10 -9.1(3) . . . . ?
C14 N2 C10 C11 0.6(4) . . . . ?
Ir1 N2 C10 C11 -173.3(2) . . . . ?
C14 N2 C10 C9 -175.7(3) . . . . ?
Ir1 N2 C10 C9 10.4(3) . . . . ?
O1 C9 C10 N2 175.4(3) . . . . ?
N1 C9 C10 N2 -1.0(4) . . . . ?
O1 C9 C10 C11 -0.8(5) . . . . ?
N1 C9 C10 C11 -177.3(3) . . . . ?
N2 C10 C11 C12 -1.7(4) . . . . ?
C9 C10 C11 C12 174.3(3) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C10 N2 C14 C13 1.4(4) . . . . ?
Ir1 N2 C14 C13 174.6(2) . . . . ?
C12 C13 C14 N2 -2.2(4) . . . . ?
C19 C15 C16 C17 -2.0(3) . . . . ?
C20 C15 C16 C17 175.0(3) . . . . ?
Ir1 C15 C16 C17 -62.01(19) . . . . ?
C19 C15 C16 C21 -177.2(3) . . . . ?
C20 C15 C16 C21 -0.2(5) . . . . ?
Ir1 C15 C16 C21 122.8(3) . . . . ?
C19 C15 C16 Ir1 60.02(19) . . . . ?
C20 C15 C16 Ir1 -123.0(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C21 C16 C17 C18 176.2(3) . . . . ?
Ir1 C16 C17 C18 -60.84(19) . . . . ?
C15 C16 C17 C22 -177.7(3) . . . . ?
C21 C16 C17 C22 -2.4(5) . . . . ?
Ir1 C16 C17 C22 120.5(3) . . . . ?
C15 C16 C17 Ir1 61.75(19) . . . . ?
C21 C16 C17 Ir1 -123.0(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C22 C17 C18 C19 179.1(3) . . . . ?
Ir1 C17 C18 C19 -59.77(18) . . . . ?
C16 C17 C18 C23 -171.8(3) . . . . ?
C22 C17 C18 C23 6.8(5) . . . . ?
Ir1 C17 C18 C23 127.9(3) . . . . ?
C16 C17 C18 Ir1 60.27(19) . . . . ?
C22 C17 C18 Ir1 -121.1(3) . . . . ?
C16 C15 C19 C18 2.3(3) . . . . ?
C20 C15 C19 C18 -174.8(3) . . . . ?
Ir1 C15 C19 C18 62.82(18) . . . . ?
C16 C15 C19 C24 173.5(3) . . . . ?
C20 C15 C19 C24 -3.6(5) . . . . ?
Ir1 C15 C19 C24 -126.0(3) . . . . ?
C16 C15 C19 Ir1 -60.52(19) . . . . ?
C20 C15 C19 Ir1 122.4(3) . . . . ?
C17 C18 C19 C15 -1.7(3) . . . . ?
C23 C18 C19 C15 170.7(3) . . . . ?
Ir1 C18 C19 C15 -62.45(18) . . . . ?
C17 C18 C19 C24 -173.1(3) . . . . ?
C23 C18 C19 C24 -0.6(4) . . . . ?
Ir1 C18 C19 C24 126.2(3) . . . . ?
C17 C18 C19 Ir1 60.73(19) . . . . ?
C23 C18 C19 Ir1 -126.8(3) . . . . ?

_refine_diff_density_max         0.844
_refine_diff_density_min         -1.139
_refine_diff_density_rms         0.078


####################################################################### 
# 
# 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_Ir4
_database_code_depnum_ccdc_archive 'CCDC 2365895'
loop_
_audit_author_name
_audit_author_address
'Loi Do'
;University of Houston
United States of America
;
_audit_update_record             
;
2024-06-26 deposited with the CCDC.	2024-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 Cl Ir N2 O'
_chemical_formula_sum            'C34 H32 Cl Ir N2 O'
_chemical_formula_weight         712.26

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'
O O 0.0106 0.0060 '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'

_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                   10.2399(2)
_cell_length_b                   14.1818(3)
_cell_length_c                   20.0309(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.1700(10)
_cell_angle_gamma                90
_cell_volume                     2843.52(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7519
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      24.61

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    4.819
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.6506
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   EMPIRICAL
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            21630
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.773
_diffrn_reflns_theta_max         25.183
_diffrn_reflns_theta_full        25.183
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5096
_reflns_number_gt                4241
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0182P)²+7.8656P] 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         5096
_refine_ls_number_parameters     297
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0622
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.59818(11) 0.55744(8) 0.66021(7) 0.0260(3) Uani 1 1 d . . . . .
O1 O 0.6535(3) 0.3540(2) 0.62057(16) 0.0195(7) Uani 1 1 d . . . . .
Ir1 Ir 0.77229(2) 0.47453(2) 0.62082(2) 0.01683(7) Uani 1 1 d . . . . .
N1 N 0.8292(3) 0.4272(3) 0.72148(18) 0.0164(8) Uani 1 1 d . . . . .
C1 C 0.9144(4) 0.4704(3) 0.7724(2) 0.0200(10) Uani 1 1 d . . . . .
H1 H 0.946884 0.531301 0.764660 0.024 Uiso 1 1 calc R U . . .
N2 N 0.6114(3) 0.2298(3) 0.68784(19) 0.0177(9) Uani 1 1 d . . . . .
C2 C 0.9559(4) 0.4292(4) 0.8356(2) 0.0224(11) Uani 1 1 d . . . . .
H2 H 1.014884 0.461767 0.871141 0.027 Uiso 1 1 calc R U . . .
C3 C 0.9107(4) 0.3398(3) 0.8467(3) 0.0238(11) Uani 1 1 d . . . . .
H3 H 0.941400 0.308902 0.889173 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8205(4) 0.2963(3) 0.7950(2) 0.0193(11) Uani 1 1 d . . . . .
H4 H 0.787358 0.235215 0.801820 0.023 Uiso 1 1 calc R U . . .
C5 C 0.7788(4) 0.3419(3) 0.7337(2) 0.0148(10) Uani 1 1 d . . . . .
C6 C 0.6753(4) 0.3047(3) 0.6767(2) 0.0161(10) Uani 1 1 d . . . . .
C7 C 0.5122(4) 0.1953(3) 0.6333(2) 0.0160(10) Uani 1 1 d . . . . .
C8 C 0.5454(4) 0.1475(3) 0.5775(2) 0.0188(11) Uani 1 1 d . . . . .
C9 C 0.4428(4) 0.1132(3) 0.5262(2) 0.0215(11) Uani 1 1 d . . . . .
H9 H 0.464839 0.082224 0.488011 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3102(4) 0.1228(3) 0.5292(3) 0.0234(12) Uani 1 1 d . . . . .
H10 H 0.241821 0.099951 0.493201 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2785(4) 0.1661(3) 0.5854(3) 0.0233(12) Uani 1 1 d . . . . .
H11 H 0.187466 0.170479 0.588629 0.028 Uiso 1 1 calc R U . . .
C12 C 0.3765(4) 0.2034(3) 0.6373(2) 0.0179(10) Uani 1 1 d . . . . .
C13 C 0.3348(5) 0.2493(5) 0.6965(3) 0.0440(7) Uani 1 1 d . U . . .
C14 C 0.2411(5) 0.2030(5) 0.7269(3) 0.0440(7) Uani 1 1 d . U . . .
H14 H 0.206608 0.143735 0.709357 0.053 Uiso 1 1 calc R U . . .
C15 C 0.1981(5) 0.2417(4) 0.7817(3) 0.0440(7) Uani 1 1 d . U . . .
H15 H 0.134409 0.209652 0.801648 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2472(5) 0.3249(4) 0.8062(3) 0.0440(7) Uani 1 1 d . U . . .
H16 H 0.220143 0.350220 0.845026 0.053 Uiso 1 1 calc R U . . .
C17 C 0.3365(5) 0.3756(5) 0.7768(3) 0.0440(7) Uani 1 1 d . U . . .
H17 H 0.367313 0.435649 0.794472 0.053 Uiso 1 1 calc R U . . .
C18 C 0.3810(5) 0.3373(5) 0.7206(3) 0.0440(7) Uani 1 1 d . U . . .
H18 H 0.441571 0.371246 0.699615 0.053 Uiso 1 1 calc R U . . .
C19 C 0.6861(5) 0.1270(4) 0.5733(3) 0.0318(5) Uani 1 1 d . U . . .
C20 C 0.7803(5) 0.0972(3) 0.6309(3) 0.0318(5) Uani 1 1 d . U . . .
H20 H 0.757345 0.095691 0.674456 0.038 Uiso 1 1 calc R U . . .
C21 C 0.9077(5) 0.0700(4) 0.6241(3) 0.0318(5) Uani 1 1 d . U . . .
H21 H 0.970948 0.048713 0.662870 0.038 Uiso 1 1 calc R U . . .
C22 C 0.9418(5) 0.0737(4) 0.5616(3) 0.0318(5) Uani 1 1 d . U . . .
H22 H 1.028452 0.054190 0.557363 0.038 Uiso 1 1 calc R U . . .
C23 C 0.8525(5) 0.1052(3) 0.5052(3) 0.0318(5) Uani 1 1 d . U . . .
H23 H 0.878149 0.109018 0.462391 0.038 Uiso 1 1 calc R U . . .
C24 C 0.7248(5) 0.1314(3) 0.5105(3) 0.0318(5) Uani 1 1 d . U . . .
H24 H 0.662948 0.152561 0.471158 0.038 Uiso 1 1 calc R U . . .
C25 C 0.7963(4) 0.4512(3) 0.5175(2) 0.0197(11) Uani 1 1 d . . . . .
C26 C 0.9180(4) 0.4286(3) 0.5662(2) 0.0206(11) Uani 1 1 d . . . . .
C27 C 0.9641(4) 0.5137(3) 0.6019(3) 0.0226(11) Uani 1 1 d . . . . .
C28 C 0.8703(5) 0.5874(3) 0.5791(2) 0.0230(11) Uani 1 1 d . . . . .
C29 C 0.7648(5) 0.5481(3) 0.5254(3) 0.0230(11) Uani 1 1 d . . . . .
C30 C 0.7138(5) 0.3810(4) 0.4714(3) 0.0288(12) Uani 1 1 d . . . . .
H30A H 0.638495 0.413266 0.441866 0.043 Uiso 1 1 calc R U . . .
H30B H 0.679910 0.333353 0.498804 0.043 Uiso 1 1 calc R U . . .
H30C H 0.768842 0.350476 0.443112 0.043 Uiso 1 1 calc R U . . .
C31 C 0.9885(5) 0.3360(3) 0.5740(3) 0.0294(13) Uani 1 1 d . . . . .
H31A H 0.922916 0.284959 0.563046 0.044 Uiso 1 1 calc R U . . .
H31B H 1.038292 0.328948 0.621184 0.044 Uiso 1 1 calc R U . . .
H31C H 1.050540 0.333200 0.542902 0.044 Uiso 1 1 calc R U . . .
C32 C 1.0916(5) 0.5227(4) 0.6548(3) 0.0336(13) Uani 1 1 d . . . . .
H32A H 1.167712 0.523637 0.632280 0.050 Uiso 1 1 calc R U . . .
H32B H 1.100114 0.468981 0.686187 0.050 Uiso 1 1 calc R U . . .
H32C H 1.089921 0.581405 0.680457 0.050 Uiso 1 1 calc R U . . .
C33 C 0.8851(5) 0.6889(3) 0.6009(3) 0.0339(13) Uani 1 1 d . . . . .
H33A H 0.947793 0.720368 0.577382 0.051 Uiso 1 1 calc R U . . .
H33B H 0.919158 0.692229 0.650331 0.051 Uiso 1 1 calc R U . . .
H33C H 0.797943 0.720190 0.589082 0.051 Uiso 1 1 calc R U . . .
C34 C 0.6479(5) 0.6014(4) 0.4860(3) 0.0328(13) Uani 1 1 d . . . . .
H34A H 0.676248 0.639530 0.450814 0.049 Uiso 1 1 calc R U . . .
H34B H 0.612092 0.642717 0.517043 0.049 Uiso 1 1 calc R U . . .
H34C H 0.578618 0.556880 0.464346 0.049 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
Cl1 Ir1 2.4035(11) . ?
O1 C6 1.303(5) . ?
O1 Ir1 2.097(3) . ?
Ir1 N1 2.088(4) . ?
Ir1 C26 2.130(4) . ?
Ir1 C28 2.150(4) . ?
Ir1 C27 2.151(4) . ?
Ir1 C25 2.159(5) . ?
Ir1 C29 2.165(5) . ?
N1 C1 1.343(6) . ?
N1 C5 1.357(6) . ?
C1 C2 1.378(6) . ?
N2 C6 1.291(6) . ?
N2 C7 1.413(5) . ?
C2 C3 1.383(7) . ?
C3 C4 1.379(6) . ?
C4 C5 1.375(6) . ?
C5 C6 1.482(6) . ?
C7 C8 1.410(6) . ?
C7 C12 1.414(6) . ?
C8 C9 1.393(6) . ?
C8 C19 1.489(6) . ?
C9 C10 1.378(6) . ?
C10 C11 1.379(7) . ?
C11 C12 1.389(6) . ?
C12 C13 1.492(7) . ?
C13 C18 1.385(8) . ?
C13 C14 1.403(8) . ?
C14 C15 1.380(8) . ?
C15 C16 1.334(8) . ?
C16 C17 1.387(8) . ?
C17 C18 1.410(8) . ?
C19 C24 1.396(7) . ?
C19 C20 1.404(7) . ?
C20 C21 1.395(6) . ?
C21 C22 1.369(7) . ?
C22 C23 1.370(7) . ?
C23 C24 1.385(6) . ?
C25 C29 1.428(6) . ?
C25 C26 1.446(6) . ?
C25 C30 1.493(6) . ?
C26 C27 1.433(7) . ?
C26 C31 1.491(6) . ?
C27 C28 1.428(7) . ?
C27 C32 1.503(7) . ?
C28 C29 1.464(7) . ?
C28 C33 1.502(7) . ?
C29 C34 1.492(6) . ?

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
C6 O1 Ir1 116.2(3) . . ?
N1 Ir1 O1 77.52(13) . . ?
N1 Ir1 C26 108.33(16) . . ?
O1 Ir1 C26 102.62(15) . . ?
N1 Ir1 C28 123.84(17) . . ?
O1 Ir1 C28 157.50(16) . . ?
C26 Ir1 C28 65.99(18) . . ?
N1 Ir1 C27 100.00(16) . . ?
O1 Ir1 C27 139.59(16) . . ?
C26 Ir1 C27 39.10(18) . . ?
C28 Ir1 C27 38.78(18) . . ?
N1 Ir1 C25 144.15(16) . . ?
O1 Ir1 C25 93.22(15) . . ?
C26 Ir1 C25 39.41(17) . . ?
C28 Ir1 C25 65.46(17) . . ?
C27 Ir1 C25 65.05(18) . . ?
N1 Ir1 C29 163.38(16) . . ?
O1 Ir1 C29 118.57(15) . . ?
C26 Ir1 C29 65.92(18) . . ?
C28 Ir1 C29 39.66(18) . . ?
C27 Ir1 C29 65.38(18) . . ?
C25 Ir1 C29 38.57(17) . . ?
N1 Ir1 Cl1 85.18(10) . . ?
O1 Ir1 Cl1 85.94(9) . . ?
C26 Ir1 Cl1 165.18(13) . . ?
C28 Ir1 Cl1 101.69(13) . . ?
C27 Ir1 Cl1 134.39(14) . . ?
C25 Ir1 Cl1 129.17(12) . . ?
C29 Ir1 Cl1 99.40(13) . . ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Ir1 126.2(3) . . ?
C5 N1 Ir1 114.9(3) . . ?
N1 C1 C2 122.0(4) . . ?
C6 N2 C7 117.4(4) . . ?
C1 C2 C3 119.1(4) . . ?
C4 C3 C2 119.0(5) . . ?
C5 C4 C3 119.5(4) . . ?
N1 C5 C4 121.5(4) . . ?
N1 C5 C6 114.6(4) . . ?
C4 C5 C6 123.9(4) . . ?
N2 C6 O1 126.1(4) . . ?
N2 C6 C5 117.7(4) . . ?
O1 C6 C5 116.0(4) . . ?
C8 C7 N2 121.7(4) . . ?
C8 C7 C12 119.2(4) . . ?
N2 C7 C12 118.9(4) . . ?
C9 C8 C7 118.8(4) . . ?
C9 C8 C19 118.6(4) . . ?
C7 C8 C19 122.5(4) . . ?
C10 C9 C8 122.0(5) . . ?
C9 C10 C11 118.9(4) . . ?
C10 C11 C12 121.6(4) . . ?
C11 C12 C7 119.4(4) . . ?
C11 C12 C13 118.6(4) . . ?
C7 C12 C13 122.0(4) . . ?
C18 C13 C14 119.0(6) . . ?
C18 C13 C12 122.4(5) . . ?
C14 C13 C12 118.5(5) . . ?
C15 C14 C13 121.4(6) . . ?
C16 C15 C14 119.0(6) . . ?
C15 C16 C17 122.2(6) . . ?
C16 C17 C18 119.4(6) . . ?
C13 C18 C17 118.8(6) . . ?
C24 C19 C20 118.5(5) . . ?
C24 C19 C8 120.2(5) . . ?
C20 C19 C8 121.1(5) . . ?
C21 C20 C19 119.8(5) . . ?
C22 C21 C20 120.2(5) . . ?
C21 C22 C23 120.8(5) . . ?
C22 C23 C24 120.1(5) . . ?
C23 C24 C19 120.6(5) . . ?
C29 C25 C26 108.8(4) . . ?
C29 C25 C30 126.7(4) . . ?
C26 C25 C30 124.3(4) . . ?
C29 C25 Ir1 70.9(3) . . ?
C26 C25 Ir1 69.2(3) . . ?
C30 C25 Ir1 122.1(3) . . ?
C27 C26 C25 107.2(4) . . ?
C27 C26 C31 126.1(4) . . ?
C25 C26 C31 126.5(4) . . ?
C27 C26 Ir1 71.2(3) . . ?
C25 C26 Ir1 71.4(3) . . ?
C31 C26 Ir1 126.3(3) . . ?
C28 C27 C26 109.1(4) . . ?
C28 C27 C32 126.1(5) . . ?
C26 C27 C32 124.7(4) . . ?
C28 C27 Ir1 70.6(2) . . ?
C26 C27 Ir1 69.7(2) . . ?
C32 C27 Ir1 126.0(3) . . ?
C27 C28 C29 107.4(4) . . ?
C27 C28 C33 126.0(4) . . ?
C29 C28 C33 126.3(4) . . ?
C27 C28 Ir1 70.6(3) . . ?
C29 C28 Ir1 70.7(3) . . ?
C33 C28 Ir1 128.8(3) . . ?
C25 C29 C28 107.4(4) . . ?
C25 C29 C34 127.1(4) . . ?
C28 C29 C34 125.5(4) . . ?
C25 C29 Ir1 70.5(3) . . ?
C28 C29 Ir1 69.6(3) . . ?
C34 C29 Ir1 125.8(3) . . ?

_refine_diff_density_max         1.372
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.127

