# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_leung788
_database_code_depnum_ccdc_archive 'CCDC 1815863'
_audit_update_record             
;
2018-08-04 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H29 Cl Ir N'
_chemical_formula_iupac          ?
_chemical_formula_weight         547.12
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   7.8309(9)
_cell_length_b                   18.449(2)
_cell_length_c                   28.858(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4169.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8791
_cell_measurement_theta_min      5.0958
_cell_measurement_theta_max      29.2505
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.260
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2144

_exptl_absorpt_coefficient_mu    6.539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.18
_exptl_absorpt_correction_T_max  0.28

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            35193
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_theta_min         5.10
_diffrn_reflns_theta_max         31.08
_diffrn_reflns_theta_full        31.08
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       41

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             13198
_reflns_number_gt                11509
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0646
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.967
_refine_ls_number_reflns         13198
_refine_ls_number_parameters     571
_refine_ls_number_restraints     595
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0117P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.375
_refine_diff_density_min         -1.503
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.021(8)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2016)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5256(8) -0.0289(4) 0.6347(2) 0.0125(13) Uani d . . . 1.0 . .
C C2 0.6639(9) -0.0595(4) 0.6598(2) 0.0146(14) Uani d . . . 1.0 . .
H H2 0.70597 -0.034845 0.686315 0.018 Uiso calc U . R 1.0 . .
C C3 0.7378(9) -0.1232(4) 0.6470(2) 0.0177(14) Uani d . . . 1.0 . .
H H3 0.828568 -0.142372 0.665056 0.021 Uiso calc U . R 1.0 . .
C C4 0.6816(9) -0.1615(4) 0.6069(2) 0.0150(14) Uani d . . . 1.0 . .
C C5 0.7586(10) -0.2267(4) 0.5927(2) 0.0209(16) Uani d . . . 1.0 . .
H H5 0.849687 -0.24645 0.610461 0.025 Uiso calc U . R 1.0 . .
C C6 0.7044(11) -0.2622(4) 0.5538(3) 0.0265(18) Uani d . . . 1.0 . .
H H6 0.759685 -0.305491 0.54413 0.032 Uiso calc U . R 1.0 . .
C C7 0.5649(12) -0.2340(4) 0.5279(2) 0.0267(18) Uani d . . . 1.0 . .
H H7 0.525349 -0.258904 0.501143 0.032 Uiso calc U . R 1.0 . .
C C8 0.4886(10) -0.1717(4) 0.5414(2) 0.0202(16) Uani d . . . 1.0 . .
H H8 0.396323 -0.153257 0.523602 0.024 Uiso calc U . R 1.0 . .
C C9 0.5422(9) -0.1330(4) 0.5815(2) 0.0150(14) Uani d . . . 1.0 . .
C C10 0.4647(9) -0.0665(4) 0.5960(2) 0.0150(14) Uani d . . . 1.0 . .
C C11 0.3153(10) -0.0338(4) 0.5717(2) 0.0181(15) Uani d . . . 1.0 . .
H H11 0.326407 -0.042655 0.537688 0.022 Uiso calc U . R 1.0 . .
C C12 0.1480(10) -0.0658(4) 0.5887(3) 0.0260(17) Uani d . . . 1.0 . .
H H12A 0.146438 -0.118011 0.582395 0.039 Uiso calc U . R 1.0 . .
H H12B 0.05269 -0.042515 0.572462 0.039 Uiso calc U . R 1.0 . .
H H12C 0.13681 -0.057557 0.622077 0.039 Uiso calc U . R 1.0 . .
C C13 0.1790(12) 0.0883(5) 0.5637(2) 0.032(2) Uani d . . . 1.0 . .
H H13A 0.158987 0.076534 0.531039 0.048 Uiso calc U . R 1.0 . .
H H13B 0.202257 0.140225 0.566809 0.048 Uiso calc U . R 1.0 . .
H H13C 0.077621 0.075665 0.581906 0.048 Uiso calc U . R 1.0 . .
C C14 0.2023(9) 0.0674(4) 0.6956(2) 0.0158(14) Uani d . . . 1.0 . .
C C15 0.2210(9) 0.1436(4) 0.6825(2) 0.0163(15) Uani d . . . 1.0 . .
C C16 0.3828(10) 0.1661(4) 0.6957(2) 0.0198(16) Uani d . . . 1.0 . .
C C17 0.4717(9) 0.1065(4) 0.7191(2) 0.0163(15) Uani d . . . 1.0 . .
C C18 0.3548(9) 0.0468(4) 0.7201(2) 0.0142(14) Uani d . . . 1.0 . .
C C19 0.0379(10) 0.0260(4) 0.6950(2) 0.0229(17) Uani d . . . 1.0 . .
H H19A 0.06227 -0.026057 0.693729 0.034 Uiso calc U . R 1.0 . .
H H19B -0.028767 0.040077 0.667701 0.034 Uiso calc U . R 1.0 . .
H H19C -0.027343 0.036906 0.723117 0.034 Uiso calc U . R 1.0 . .
C C20 0.0848(12) 0.1882(4) 0.6595(2) 0.0249(16) Uani d . . . 1.0 . .
H H20A 0.017519 0.213325 0.683194 0.037 Uiso calc U . R 1.0 . .
H H20B 0.009953 0.156411 0.641395 0.037 Uiso calc U . R 1.0 . .
H H20C 0.138106 0.22387 0.638933 0.037 Uiso calc U . R 1.0 . .
C C21 0.4596(12) 0.2391(4) 0.6881(3) 0.032(2) Uani d . . . 1.0 . .
H H21A 0.405878 0.262027 0.661168 0.047 Uiso calc U . R 1.0 . .
H H21B 0.582477 0.233984 0.682555 0.047 Uiso calc U . R 1.0 . .
H H21C 0.440905 0.269199 0.71561 0.047 Uiso calc U . R 1.0 . .
C C22 0.6384(10) 0.1129(5) 0.7438(3) 0.0261(18) Uani d . . . 1.0 . .
H H22A 0.621789 0.138969 0.773036 0.039 Uiso calc U . R 1.0 . .
H H22B 0.719489 0.139567 0.72433 0.039 Uiso calc U . R 1.0 . .
H H22C 0.683578 0.064385 0.750218 0.039 Uiso calc U . R 1.0 . .
C C23 0.3808(11) -0.0234(4) 0.7445(2) 0.0210(17) Uani d . . . 1.0 . .
H H23A 0.503041 -0.034581 0.745631 0.031 Uiso calc U . R 1.0 . .
H H23B 0.320548 -0.061923 0.727816 0.031 Uiso calc U . R 1.0 . .
H H23C 0.335899 -0.019762 0.776101 0.031 Uiso calc U . R 1.0 . .
C C24 0.5504(9) 0.9442(3) 0.3742(2) 0.0158(15) Uani d . . . 1.0 . .
C C25 0.4239(11) 0.9398(4) 0.3386(2) 0.0202(14) Uani d . . . 1.0 . .
H H25 0.348544 0.979436 0.333863 0.024 Uiso calc U . R 1.0 . .
C C26 0.4094(11) 0.8798(4) 0.3114(2) 0.0206(15) Uani d . . . 1.0 . .
H H26 0.321591 0.87775 0.288721 0.025 Uiso calc U . R 1.0 . .
C C27 0.5229(9) 0.8202(4) 0.3162(2) 0.0174(15) Uani d . . . 1.0 . .
C C28 0.5200(10) 0.7602(4) 0.2862(2) 0.0219(17) Uani d . . . 1.0 . .
H H28 0.436989 0.758139 0.262206 0.026 Uiso calc U . R 1.0 . .
C C29 0.6345(12) 0.7047(4) 0.2909(3) 0.029(2) Uani d . . . 1.0 . .
H H29 0.632717 0.665288 0.269674 0.034 Uiso calc U . R 1.0 . .
C C30 0.7546(12) 0.7059(4) 0.3269(3) 0.0278(18) Uani d . . . 1.0 . .
H H30 0.833876 0.667197 0.32992 0.033 Uiso calc U . R 1.0 . .
C C31 0.7591(11) 0.7625(4) 0.3579(2) 0.0218(16) Uani d . . . 1.0 . .
H H31 0.838577 0.76154 0.382755 0.026 Uiso calc U . R 1.0 . .
C C32 0.6462(9) 0.8223(4) 0.3532(2) 0.0198(15) Uani d . . . 1.0 . .
C C33 0.6509(10) 0.8844(4) 0.3826(2) 0.0185(15) Uani d . . . 1.0 . .
C C34 0.7684(11) 0.8888(4) 0.4234(2) 0.0247(18) Uani d . . . 1.0 . .
H H34 0.765703 0.841516 0.440313 0.03 Uiso calc U . R 1.0 . .
C C35 0.9528(11) 0.9064(4) 0.4107(3) 0.039(2) Uani d . . . 1.0 . .
H H35A 0.959509 0.956084 0.398878 0.059 Uiso calc U . R 1.0 . .
H H35B 0.99238 0.872575 0.386815 0.059 Uiso calc U . R 1.0 . .
H H35C 1.025068 0.901756 0.438279 0.059 Uiso calc U . R 1.0 . .
C C36 0.7941(12) 0.9634(4) 0.4965(3) 0.035(2) Uani d . . . 1.0 . .
H H36A 0.821288 0.918081 0.512661 0.052 Uiso calc U . R 1.0 . .
H H36B 0.727748 0.994891 0.517103 0.052 Uiso calc U . R 1.0 . .
H H36C 0.900143 0.987901 0.48766 0.052 Uiso calc U . R 1.0 . .
C C37 0.7968(14) 1.0998(12) 0.3808(5) 0.017(2) Uani d U P DG 0.60(3) A 1
C C38 0.7668(16) 1.1273(13) 0.4261(4) 0.017(2) Uani d U P DG 0.60(3) A 1
C C39 0.5935(17) 1.1497(9) 0.4286(4) 0.021(2) Uani d U P DG 0.60(3) A 1
C C40 0.5164(12) 1.1359(8) 0.3849(5) 0.020(2) Uani d U P DG 0.60(3) A 1
C C41 0.6420(16) 1.1051(8) 0.3554(3) 0.017(2) Uani d U P DG 0.60(3) A 1
C C42 0.962(2) 1.0751(16) 0.3602(7) 0.028(4) Uani d U P D 0.60(3) A 1
H H42A 0.940073 1.035637 0.338263 0.042 Uiso calc U P R 0.60(3) A 1
H H42B 1.037694 1.057923 0.384852 0.042 Uiso calc U P R 0.60(3) A 1
H H42C 1.016007 1.115686 0.343901 0.042 Uiso calc U P R 0.60(3) A 1
C C43 0.901(3) 1.1373(14) 0.4628(6) 0.027(4) Uani d U P D 0.60(3) A 1
H H43A 0.958809 1.184008 0.458279 0.04 Uiso calc U P R 0.60(3) A 1
H H43B 0.985426 1.098081 0.460632 0.04 Uiso calc U P R 0.60(3) A 1
H H43C 0.847768 1.136386 0.493499 0.04 Uiso calc U P R 0.60(3) A 1
C C44 0.509(3) 1.1859(11) 0.4698(6) 0.035(4) Uani d U P D 0.60(3) A 1
H H44A 0.581119 1.179869 0.497266 0.053 Uiso calc U P R 0.60(3) A 1
H H44B 0.39733 1.163652 0.475345 0.053 Uiso calc U P R 0.60(3) A 1
H H44C 0.494147 1.237697 0.463331 0.053 Uiso calc U P R 0.60(3) A 1
C C45 0.3353(19) 1.1561(11) 0.3715(8) 0.037(4) Uani d U P D 0.60(3) A 1
H H45A 0.331877 1.207042 0.361921 0.056 Uiso calc U P R 0.60(3) A 1
H H45B 0.259483 1.148966 0.398127 0.056 Uiso calc U P R 0.60(3) A 1
H H45C 0.297592 1.12534 0.34578 0.056 Uiso calc U P R 0.60(3) A 1
C C46 0.626(3) 1.0878(10) 0.3047(4) 0.026(4) Uani d U P D 0.60(3) A 1
H H46A 0.504691 1.084508 0.296391 0.038 Uiso calc U P R 0.60(3) A 1
H H46B 0.681902 1.0414 0.298229 0.038 Uiso calc U P R 0.60(3) A 1
H H46C 0.680166 1.126161 0.286448 0.038 Uiso calc U P R 0.60(3) A 1
C C37A 0.779(3) 1.0957(19) 0.3791(8) 0.016(3) Uani d U P D 0.40(3) A 2
C C38A 0.787(3) 1.127(2) 0.4258(8) 0.015(3) Uani d U P D 0.40(3) A 2
C C39A 0.627(3) 1.1557(15) 0.4380(7) 0.017(3) Uani d U P D 0.40(3) A 2
C C40A 0.515(3) 1.1480(14) 0.3978(8) 0.020(3) Uani d U P D 0.40(3) A 2
C C41A 0.615(3) 1.1176(15) 0.3613(7) 0.018(3) Uani d U P D 0.40(3) A 2
C C42A 0.927(4) 1.073(2) 0.3495(10) 0.026(5) Uani d U P D 0.40(3) A 2
H H42D 0.899155 1.027557 0.333727 0.038 Uiso calc U P R 0.40(3) A 2
H H42E 1.027961 1.066187 0.368993 0.038 Uiso calc U P R 0.40(3) A 2
H H42F 0.949869 1.110806 0.326419 0.038 Uiso calc U P R 0.40(3) A 2
C C43A 0.944(3) 1.125(2) 0.4556(10) 0.020(5) Uani d U P D 0.40(3) A 2
H H43D 0.996933 1.173449 0.455698 0.031 Uiso calc U P R 0.40(3) A 2
H H43E 1.024828 1.089745 0.443269 0.031 Uiso calc U P R 0.40(3) A 2
H H43F 0.912337 1.111925 0.487341 0.031 Uiso calc U P R 0.40(3) A 2
C C44A 0.573(4) 1.1913(15) 0.4832(8) 0.030(5) Uani d U P D 0.40(3) A 2
H H44D 0.644813 1.173665 0.508476 0.045 Uiso calc U P R 0.40(3) A 2
H H44E 0.453055 1.179249 0.489638 0.045 Uiso calc U P R 0.40(3) A 2
H H44F 0.584677 1.244031 0.480453 0.045 Uiso calc U P R 0.40(3) A 2
C C45A 0.335(3) 1.1762(15) 0.3928(11) 0.032(5) Uani d U P D 0.40(3) A 2
H H45D 0.337872 1.228206 0.386002 0.047 Uiso calc U P R 0.40(3) A 2
H H45E 0.272101 1.168075 0.421764 0.047 Uiso calc U P R 0.40(3) A 2
H H45F 0.277463 1.150575 0.367469 0.047 Uiso calc U P R 0.40(3) A 2
C C46A 0.562(4) 1.1084(16) 0.3111(7) 0.030(5) Uani d U P D 0.40(3) A 2
H H46D 0.436944 1.105797 0.309149 0.045 Uiso calc U P R 0.40(3) A 2
H H46E 0.611415 1.063707 0.298672 0.045 Uiso calc U P R 0.40(3) A 2
H H46F 0.602494 1.149907 0.292964 0.045 Uiso calc U P R 0.40(3) A 2
Cl Cl1 0.6549(3) 0.12167(10) 0.60636(6) 0.0251(4) Uani d . . . 1.0 . .
Cl Cl2 0.3312(3) 1.00613(11) 0.45292(6) 0.0272(4) Uani d . . . 1.0 . .
Ir Ir1 0.41800(4) 0.06889(2) 0.64927(2) 0.01168(6) Uani d . . . 1.0 . .
Ir Ir2 0.59392(4) 1.03436(2) 0.41340(2) 0.01669(6) Uani d . . . 1.0 . .
N N1 0.3281(8) 0.0463(3) 0.58098(18) 0.0168(13) Uani d . . . 1.0 . .
H H1 0.424076 0.0624 0.560569 0.02 Uiso calc U . R 1.0 . .
N N2 0.6923(8) 0.9470(3) 0.4543(2) 0.0227(15) Uani d . . . 1.0 . .
H H2A 0.587087 0.923519 0.466873 0.027 Uiso calc U . R 1.0 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C10 . 1.397(9) ?
C1 C2 . 1.421(9) ?
C1 Ir1 . 2.035(7) ?
C2 C3 . 1.360(9) ?
C2 H2 . 0.95 ?
C3 C4 . 1.424(9) ?
C3 H3 . 0.95 ?
C4 C5 . 1.407(10) ?
C4 C9 . 1.417(9) ?
C5 C6 . 1.368(10) ?
C5 H5 . 0.95 ?
C6 C7 . 1.423(12) ?
C6 H6 . 0.95 ?
C7 C8 . 1.353(10) ?
C7 H7 . 0.95 ?
C8 C9 . 1.423(9) ?
C8 H8 . 0.95 ?
C9 C10 . 1.432(9) ?
C10 C11 . 1.491(9) ?
C11 N1 . 1.505(9) ?
C11 C12 . 1.518(10) ?
C11 H11 . 1.0 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 N1 . 1.487(10) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 C18 . 1.438(10) ?
C14 C15 . 1.464(10) ?
C14 C19 . 1.497(10) ?
C14 Ir1 . 2.155(7) ?
C15 C16 . 1.386(10) ?
C15 C20 . 1.500(10) ?
C15 Ir1 . 2.281(7) ?
C16 C17 . 1.467(10) ?
C16 C21 . 1.491(10) ?
C16 Ir1 . 2.254(6) ?
C17 C18 . 1.432(10) ?
C17 C22 . 1.492(10) ?
C17 Ir1 . 2.173(7) ?
C18 C23 . 1.488(9) ?
C18 Ir1 . 2.141(6) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?
C24 C33 . 1.377(10) ?
C24 C25 . 1.429(9) ?
C24 Ir2 . 2.041(7) ?
C25 C26 . 1.362(9) ?
C25 H25 . 0.95 ?
C26 C27 . 1.421(10) ?
C26 H26 . 0.95 ?
C27 C28 . 1.406(10) ?
C27 C32 . 1.439(10) ?
C28 C29 . 1.368(11) ?
C28 H28 . 0.95 ?
C29 C30 . 1.402(11) ?
C29 H29 . 0.95 ?
C30 C31 . 1.375(10) ?
C30 H30 . 0.95 ?
C31 C32 . 1.420(10) ?
C31 H31 . 0.95 ?
C32 C33 . 1.426(10) ?
C33 C34 . 1.498(10) ?
C34 N2 . 1.517(10) ?
C34 C35 . 1.524(12) ?
C34 H34 . 1.0 ?
C35 H35A . 0.98 ?
C35 H35B . 0.98 ?
C35 H35C . 0.98 ?
C36 N2 . 1.488(9) ?
C36 H36A . 0.98 ?
C36 H36B . 0.98 ?
C36 H36C . 0.98 ?
C37 C38 . 1.42 ?
C37 C41 . 1.42 ?
C37 C42 . 1.494(13) ?
C37 Ir2 . 2.205(19) ?
C38 C39 . 1.42 ?
C38 C43 . 1.508(13) ?
C38 Ir2 . 2.22(2) ?
C39 C40 . 1.42 ?
C39 C44 . 1.516(13) ?
C39 Ir2 . 2.172(15) ?
C40 C41 . 1.42 ?
C40 C45 . 1.516(14) ?
C40 Ir2 . 2.134(14) ?
C41 C46 . 1.503(12) ?
C41 Ir2 . 2.155(14) ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
C43 H43A . 0.98 ?
C43 H43B . 0.98 ?
C43 H43C . 0.98 ?
C44 H44A . 0.98 ?
C44 H44B . 0.98 ?
C44 H44C . 0.98 ?
C45 H45A . 0.98 ?
C45 H45B . 0.98 ?
C45 H45C . 0.98 ?
C46 H46A . 0.98 ?
C46 H46B . 0.98 ?
C46 H46C . 0.98 ?
C37A C41A . 1.442(19) ?
C37A C38A . 1.465(17) ?
C37A C42A . 1.498(19) ?
C37A Ir2 . 2.09(3) ?
C38A C39A . 1.406(18) ?
C38A C43A . 1.501(19) ?
C38A Ir2 . 2.31(3) ?
C39A C40A . 1.463(18) ?
C39A C44A . 1.519(18) ?
C39A Ir2 . 2.36(3) ?
C40A C41A . 1.431(18) ?
C40A C45A . 1.508(19) ?
C40A Ir2 . 2.23(2) ?
C41A C46A . 1.516(18) ?
C41A Ir2 . 2.16(2) ?
C42A H42D . 0.98 ?
C42A H42E . 0.98 ?
C42A H42F . 0.98 ?
C43A H43D . 0.98 ?
C43A H43E . 0.98 ?
C43A H43F . 0.98 ?
C44A H44D . 0.98 ?
C44A H44E . 0.98 ?
C44A H44F . 0.98 ?
C45A H45D . 0.98 ?
C45A H45E . 0.98 ?
C45A H45F . 0.98 ?
C46A H46D . 0.98 ?
C46A H46E . 0.98 ?
C46A H46F . 0.98 ?
Cl1 Ir1 . 2.4339(18) ?
Cl2 Ir2 . 2.410(2) ?
Ir1 N1 . 2.134(5) ?
Ir2 N2 . 2.140(6) ?
N1 H1 . 1.0 ?
N2 H2A . 1.0 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 C1 C2 . . 118.0(6) ?
C10 C1 Ir1 . . 117.7(5) ?
C2 C1 Ir1 . . 124.3(5) ?
C3 C2 C1 . . 122.0(6) ?
C3 C2 H2 . . 119.0 ?
C1 C2 H2 . . 119.0 ?
C2 C3 C4 . . 121.2(6) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C9 . . 119.8(6) ?
C5 C4 C3 . . 121.9(6) ?
C9 C4 C3 . . 118.3(6) ?
C6 C5 C4 . . 121.1(7) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C7 . . 119.7(7) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C8 C7 C6 . . 119.9(7) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C7 C8 C9 . . 122.0(7) ?
C7 C8 H8 . . 119.0 ?
C9 C8 H8 . . 119.0 ?
C4 C9 C8 . . 117.6(6) ?
C4 C9 C10 . . 119.5(6) ?
C8 C9 C10 . . 122.9(6) ?
C1 C10 C9 . . 121.0(6) ?
C1 C10 C11 . . 116.2(6) ?
C9 C10 C11 . . 122.7(6) ?
C10 C11 N1 . . 105.1(6) ?
C10 C11 C12 . . 111.7(6) ?
N1 C11 C12 . . 112.5(6) ?
C10 C11 H11 . . 109.2 ?
N1 C11 H11 . . 109.2 ?
C12 C11 H11 . . 109.2 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C13 H13A . . 109.5 ?
N1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C18 C14 C15 . . 107.4(6) ?
C18 C14 C19 . . 125.8(6) ?
C15 C14 C19 . . 124.9(6) ?
C18 C14 Ir1 . . 69.9(4) ?
C15 C14 Ir1 . . 75.4(4) ?
C19 C14 Ir1 . . 132.3(5) ?
C16 C15 C14 . . 107.8(6) ?
C16 C15 C20 . . 127.4(7) ?
C14 C15 C20 . . 124.8(7) ?
C16 C15 Ir1 . . 71.2(4) ?
C14 C15 Ir1 . . 66.2(4) ?
C20 C15 Ir1 . . 128.8(5) ?
C15 C16 C17 . . 109.7(6) ?
C15 C16 C21 . . 126.7(7) ?
C17 C16 C21 . . 123.6(7) ?
C15 C16 Ir1 . . 73.2(4) ?
C17 C16 Ir1 . . 67.7(4) ?
C21 C16 Ir1 . . 125.6(5) ?
C18 C17 C16 . . 106.3(6) ?
C18 C17 C22 . . 127.7(6) ?
C16 C17 C22 . . 125.2(7) ?
C18 C17 Ir1 . . 69.4(4) ?
C16 C17 Ir1 . . 73.7(4) ?
C22 C17 Ir1 . . 129.6(5) ?
C17 C18 C14 . . 108.6(6) ?
C17 C18 C23 . . 126.2(6) ?
C14 C18 C23 . . 125.2(7) ?
C17 C18 Ir1 . . 71.8(4) ?
C14 C18 Ir1 . . 71.0(4) ?
C23 C18 Ir1 . . 125.9(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 ?
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 ?
C33 C24 C25 . . 118.5(6) ?
C33 C24 Ir2 . . 117.4(5) ?
C25 C24 Ir2 . . 124.1(5) ?
C26 C25 C24 . . 121.2(7) ?
C26 C25 H25 . . 119.4 ?
C24 C25 H25 . . 119.4 ?
C25 C26 C27 . . 121.4(7) ?
C25 C26 H26 . . 119.3 ?
C27 C26 H26 . . 119.3 ?
C28 C27 C26 . . 122.6(7) ?
C28 C27 C32 . . 119.3(7) ?
C26 C27 C32 . . 118.1(6) ?
C29 C28 C27 . . 121.2(7) ?
C29 C28 H28 . . 119.4 ?
C27 C28 H28 . . 119.4 ?
C28 C29 C30 . . 120.1(7) ?
C28 C29 H29 . . 120.0 ?
C30 C29 H29 . . 120.0 ?
C31 C30 C29 . . 120.8(8) ?
C31 C30 H30 . . 119.6 ?
C29 C30 H30 . . 119.6 ?
C30 C31 C32 . . 120.8(7) ?
C30 C31 H31 . . 119.6 ?
C32 C31 H31 . . 119.6 ?
C31 C32 C33 . . 123.5(7) ?
C31 C32 C27 . . 117.9(7) ?
C33 C32 C27 . . 118.7(7) ?
C24 C33 C32 . . 121.6(6) ?
C24 C33 C34 . . 116.5(6) ?
C32 C33 C34 . . 121.9(7) ?
C33 C34 N2 . . 105.0(6) ?
C33 C34 C35 . . 113.9(7) ?
N2 C34 C35 . . 111.3(6) ?
C33 C34 H34 . . 108.8 ?
N2 C34 H34 . . 108.8 ?
C35 C34 H34 . . 108.8 ?
C34 C35 H35A . . 109.5 ?
C34 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C34 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
N2 C36 H36A . . 109.5 ?
N2 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
N2 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C38 C37 C41 . . 108.0 ?
C38 C37 C42 . . 128.2(10) ?
C41 C37 C42 . . 123.6(9) ?
C38 C37 Ir2 . . 71.7(6) ?
C41 C37 Ir2 . . 69.1(6) ?
C42 C37 Ir2 . . 128.8(17) ?
C39 C38 C37 . . 108.0 ?
C39 C38 C43 . . 126.6(10) ?
C37 C38 C43 . . 125.1(10) ?
C39 C38 Ir2 . . 69.5(6) ?
C37 C38 Ir2 . . 70.9(6) ?
C43 C38 Ir2 . . 129.6(16) ?
C40 C39 C38 . . 108.0 ?
C40 C39 C44 . . 126.1(9) ?
C38 C39 C44 . . 125.8(9) ?
C40 C39 Ir2 . . 69.3(6) ?
C38 C39 Ir2 . . 72.8(7) ?
C44 C39 Ir2 . . 126.2(12) ?
C39 C40 C41 . . 108.0 ?
C39 C40 C45 . . 125.5(10) ?
C41 C40 C45 . . 126.4(9) ?
C39 C40 Ir2 . . 72.2(6) ?
C41 C40 Ir2 . . 71.5(6) ?
C45 C40 Ir2 . . 125.4(11) ?
C37 C41 C40 . . 108.0 ?
C37 C41 C46 . . 124.1(10) ?
C40 C41 C46 . . 127.6(9) ?
C37 C41 Ir2 . . 72.9(7) ?
C40 C41 Ir2 . . 69.9(6) ?
C46 C41 Ir2 . . 127.8(10) ?
C37 C42 H42A . . 109.5 ?
C37 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C37 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C38 C43 H43A . . 109.5 ?
C38 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
C38 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 109.5 ?
C39 C44 H44A . . 109.5 ?
C39 C44 H44B . . 109.5 ?
H44A C44 H44B . . 109.5 ?
C39 C44 H44C . . 109.5 ?
H44A C44 H44C . . 109.5 ?
H44B C44 H44C . . 109.5 ?
C40 C45 H45A . . 109.5 ?
C40 C45 H45B . . 109.5 ?
H45A C45 H45B . . 109.5 ?
C40 C45 H45C . . 109.5 ?
H45A C45 H45C . . 109.5 ?
H45B C45 H45C . . 109.5 ?
C41 C46 H46A . . 109.5 ?
C41 C46 H46B . . 109.5 ?
H46A C46 H46B . . 109.5 ?
C41 C46 H46C . . 109.5 ?
H46A C46 H46C . . 109.5 ?
H46B C46 H46C . . 109.5 ?
C41A C37A C38A . . 104.9(13) ?
C41A C37A C42A . . 124.2(18) ?
C38A C37A C42A . . 127.0(18) ?
C41A C37A Ir2 . . 72.7(13) ?
C38A C37A Ir2 . . 78.8(13) ?
C42A C37A Ir2 . . 131.(3) ?
C39A C38A C37A . . 110.0(13) ?
C39A C38A C43A . . 126.3(16) ?
C37A C38A C43A . . 123.7(17) ?
C39A C38A Ir2 . . 74.8(13) ?
C37A C38A Ir2 . . 62.7(13) ?
C43A C38A Ir2 . . 128.(3) ?
C38A C39A C40A . . 107.4(13) ?
C38A C39A C44A . . 129.0(18) ?
C40A C39A C44A . . 123.6(17) ?
C38A C39A Ir2 . . 70.2(14) ?
C40A C39A Ir2 . . 66.6(11) ?
C44A C39A Ir2 . . 129.5(18) ?
C41A C40A C39A . . 107.1(13) ?
C41A C40A C45A . . 125.2(17) ?
C39A C40A C45A . . 127.2(17) ?
C41A C40A Ir2 . . 68.1(12) ?
C39A C40A Ir2 . . 76.4(12) ?
C45A C40A Ir2 . . 127.0(17) ?
C40A C41A C37A . . 109.6(13) ?
C40A C41A C46A . . 126.7(17) ?
C37A C41A C46A . . 123.7(17) ?
C40A C41A Ir2 . . 73.9(12) ?
C37A C41A Ir2 . . 67.6(15) ?
C46A C41A Ir2 . . 124.5(17) ?
C37A C42A H42D . . 109.5 ?
C37A C42A H42E . . 109.5 ?
H42D C42A H42E . . 109.5 ?
C37A C42A H42F . . 109.5 ?
H42D C42A H42F . . 109.5 ?
H42E C42A H42F . . 109.5 ?
C38A C43A H43D . . 109.5 ?
C38A C43A H43E . . 109.5 ?
H43D C43A H43E . . 109.5 ?
C38A C43A H43F . . 109.5 ?
H43D C43A H43F . . 109.5 ?
H43E C43A H43F . . 109.5 ?
C39A C44A H44D . . 109.5 ?
C39A C44A H44E . . 109.5 ?
H44D C44A H44E . . 109.5 ?
C39A C44A H44F . . 109.5 ?
H44D C44A H44F . . 109.5 ?
H44E C44A H44F . . 109.5 ?
C40A C45A H45D . . 109.5 ?
C40A C45A H45E . . 109.5 ?
H45D C45A H45E . . 109.5 ?
C40A C45A H45F . . 109.5 ?
H45D C45A H45F . . 109.5 ?
H45E C45A H45F . . 109.5 ?
C41A C46A H46D . . 109.5 ?
C41A C46A H46E . . 109.5 ?
H46D C46A H46E . . 109.5 ?
C41A C46A H46F . . 109.5 ?
H46D C46A H46F . . 109.5 ?
H46E C46A H46F . . 109.5 ?
C1 Ir1 N1 . . 76.8(2) ?
C1 Ir1 C18 . . 97.2(2) ?
N1 Ir1 C18 . . 140.2(2) ?
C1 Ir1 C14 . . 116.2(3) ?
N1 Ir1 C14 . . 108.2(2) ?
C18 Ir1 C14 . . 39.1(2) ?
C1 Ir1 C17 . . 113.3(3) ?
N1 Ir1 C17 . . 169.4(2) ?
C18 Ir1 C17 . . 38.8(3) ?
C14 Ir1 C17 . . 65.1(3) ?
C1 Ir1 C16 . . 151.5(3) ?
N1 Ir1 C16 . . 131.6(2) ?
C18 Ir1 C16 . . 63.7(2) ?
C14 Ir1 C16 . . 63.0(3) ?
C17 Ir1 C16 . . 38.6(3) ?
C1 Ir1 C15 . . 154.6(3) ?
N1 Ir1 C15 . . 106.4(2) ?
C18 Ir1 C15 . . 63.8(2) ?
C14 Ir1 C15 . . 38.4(3) ?
C17 Ir1 C15 . . 63.1(3) ?
C16 Ir1 C15 . . 35.6(3) ?
C1 Ir1 Cl1 . . 86.20(19) ?
N1 Ir1 Cl1 . . 81.94(17) ?
C18 Ir1 Cl1 . . 137.53(19) ?
C14 Ir1 Cl1 . . 156.7(2) ?
C17 Ir1 Cl1 . . 101.3(2) ?
C16 Ir1 Cl1 . . 94.44(19) ?
C15 Ir1 Cl1 . . 119.19(19) ?
C24 Ir2 C37A . . 107.2(7) ?
C24 Ir2 C40 . . 117.1(4) ?
C24 Ir2 N2 . . 75.6(2) ?
C37A Ir2 N2 . . 114.8(7) ?
C40 Ir2 N2 . . 167.3(4) ?
C24 Ir2 C41 . . 95.3(4) ?
C40 Ir2 C41 . . 38.7(2) ?
N2 Ir2 C41 . . 145.2(4) ?
C24 Ir2 C41A . . 101.9(6) ?
C37A Ir2 C41A . . 39.7(7) ?
N2 Ir2 C41A . . 153.3(6) ?
C24 Ir2 C39 . . 155.5(4) ?
C40 Ir2 C39 . . 38.5(2) ?
N2 Ir2 C39 . . 128.8(4) ?
C41 Ir2 C39 . . 64.1(3) ?
C24 Ir2 C37 . . 109.3(4) ?
C40 Ir2 C37 . . 63.9(3) ?
N2 Ir2 C37 . . 112.8(4) ?
C41 Ir2 C37 . . 38.0(3) ?
C39 Ir2 C37 . . 63.3(4) ?
C24 Ir2 C38 . . 145.5(4) ?
C40 Ir2 C38 . . 63.7(4) ?
N2 Ir2 C38 . . 105.8(5) ?
C41 Ir2 C38 . . 63.4(4) ?
C39 Ir2 C38 . . 37.7(3) ?
C37 Ir2 C38 . . 37.5(3) ?
C24 Ir2 C40A . . 127.4(6) ?
C37A Ir2 C40A . . 65.7(8) ?
N2 Ir2 C40A . . 156.6(6) ?
C41A Ir2 C40A . . 38.0(6) ?
C24 Ir2 C38A . . 143.0(6) ?
C37A Ir2 C38A . . 38.6(7) ?
N2 Ir2 C38A . . 103.6(7) ?
C41A Ir2 C38A . . 62.1(8) ?
C40A Ir2 C38A . . 61.2(8) ?
C24 Ir2 C39A . . 163.2(6) ?
C37A Ir2 C39A . . 63.4(8) ?
N2 Ir2 C39A . . 120.5(6) ?
C41A Ir2 C39A . . 61.8(7) ?
C40A Ir2 C39A . . 37.0(6) ?
C38A Ir2 C39A . . 35.0(6) ?
C13 N1 C11 . . 113.6(6) ?
C13 N1 Ir1 . . 117.8(4) ?
C11 N1 Ir1 . . 112.2(4) ?
C13 N1 H1 . . 103.8 ?
C11 N1 H1 . . 103.8 ?
Ir1 N1 H1 . . 103.8 ?
C36 N2 C34 . . 114.5(6) ?
C36 N2 Ir2 . . 119.5(5) ?
C34 N2 Ir2 . . 110.6(4) ?
C36 N2 H2A . . 103.3 ?
C34 N2 H2A . . 103.3 ?
Ir2 N2 H2A . . 103.3 ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1815864'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H29 Cl Ir N'
_chemical_formula_iupac          ?
_chemical_formula_weight         547.12
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5640(5)
_cell_length_b                   13.4034(8)
_cell_length_c                   9.7175(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.7655(8)
_cell_angle_gamma                90
_cell_volume                     1012.85(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7357
_cell_measurement_theta_min      2.6690
_cell_measurement_theta_max      30.4845
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536

_exptl_absorpt_coefficient_mu    6.730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker 2013)'
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.50

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5788
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          'Refined as a 2-component twin.'

_reflns_number_total             5788
_reflns_number_gt                5524
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_gt          0.0533
_refine_ls_wR_factor_ref         0.0538
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_refine_ls_number_reflns         5788
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.447
_refine_diff_density_min         -1.865
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Classical Flack method preferred over Parsons because s.u. lower.'
_refine_ls_abs_structure_Flack   0.025(6)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir1 0.09395(2) 0.24605(3) 0.25983(2) 0.00866(5) Uani d . . . 1 . .
C C1 -0.1108(7) 0.3358(4) 0.1389(7) 0.0086(11) Uani d . . . 1 . .
C C2 -0.2204(8) 0.3257(5) -0.0171(7) 0.0124(12) Uani d . . . 1 . .
H H2 -0.2011 0.2723 -0.0724 0.015 Uiso calc U . R 1 . .
C C3 -0.3544(8) 0.3907(5) -0.0916(8) 0.0138(12) Uani d . . . 1 . .
H H3 -0.4267 0.3802 -0.1958 0.017 Uiso calc U . R 1 . .
C C4 -0.3855(8) 0.4722(4) -0.0155(7) 0.0102(12) Uani d . . . 1 . .
C C5 -0.5208(8) 0.5414(5) -0.0903(8) 0.0144(13) Uani d . . . 1 . .
H H5 -0.5894 0.5342 -0.196 0.017 Uiso calc U . R 1 . .
C C6 -0.5542(8) 0.6175(5) -0.0140(9) 0.0150(13) Uani d . . . 1 . .
H H6 -0.6464 0.6622 -0.0656 0.018 Uiso calc U . R 1 . .
C C7 -0.4515(9) 0.6295(5) 0.1418(8) 0.0157(13) Uani d . . . 1 . .
H H7 -0.4746 0.6829 0.1948 0.019 Uiso calc U . R 1 . .
C C8 -0.3191(8) 0.5656(4) 0.2185(8) 0.0137(13) Uani d . . . 1 . .
H H8 -0.2512 0.5756 0.3236 0.016 Uiso calc U . R 1 . .
C C9 -0.2810(8) 0.4841(4) 0.1434(7) 0.0107(12) Uani d . . . 1 . .
C C10 -0.1471(8) 0.4138(4) 0.2164(8) 0.0097(11) Uani d . . . 1 . .
C C11 -0.0434(8) 0.4137(4) 0.3859(8) 0.0108(11) Uani d . . . 1 . .
H H11A -0.0276 0.4829 0.4249 0.013 Uiso calc U . R 1 . .
H H11B -0.105 0.3756 0.4352 0.013 Uiso calc U . R 1 . .
C C12 0.2008(9) 0.3331(5) 0.5811(8) 0.0182(14) Uani d . . . 1 . .
H H12A 0.1989 0.3882 0.6465 0.027 Uiso calc U . R 1 . .
H H12B 0.3197 0.3112 0.6107 0.027 Uiso calc U . R 1 . .
H H12C 0.1325 0.2774 0.5916 0.027 Uiso calc U . R 1 . .
C C13 0.2417(10) 0.4457(5) 0.4065(10) 0.0173(16) Uani d . . . 1 . .
H H13A 0.2514 0.5006 0.4762 0.026 Uiso calc U . R 1 . .
H H13B 0.193 0.4708 0.3022 0.026 Uiso calc U . R 1 . .
H H13C 0.3559 0.4175 0.4311 0.026 Uiso calc U . R 1 . .
C C14 0.2445(9) 0.1036(5) 0.2820(8) 0.0146(13) Uani d . . . 1 . .
C C15 0.3637(8) 0.1834(5) 0.3289(8) 0.0149(13) Uani d . . . 1 . .
C C16 0.3142(7) 0.2533(9) 0.2031(8) 0.0171(13) Uani d . . . 1 . .
C C17 0.1682(8) 0.2140(4) 0.0768(8) 0.0138(13) Uani d . . . 1 . .
C C18 0.1172(8) 0.1221(4) 0.1281(8) 0.0137(13) Uani d . . . 1 . .
C C19 0.2416(12) 0.0133(5) 0.3718(11) 0.0198(17) Uani d . . . 1 . .
H H19A 0.2623 -0.0466 0.3239 0.03 Uiso calc U . R 1 . .
H H19B 0.1291 0.008 0.3751 0.03 Uiso calc U . R 1 . .
H H19C 0.3315 0.0192 0.4752 0.03 Uiso calc U . R 1 . .
C C20 0.5204(8) 0.1937(6) 0.4745(9) 0.0226(15) Uani d . . . 1 . .
H H20A 0.5297 0.2626 0.5109 0.034 Uiso calc U . R 1 . .
H H20B 0.6226 0.1768 0.4581 0.034 Uiso calc U . R 1 . .
H H20C 0.5116 0.1484 0.5502 0.034 Uiso calc U . R 1 . .
C C21 0.4240(10) 0.3387(6) 0.1931(11) 0.0272(18) Uani d . . . 1 . .
H H21A 0.4998 0.3152 0.1474 0.041 Uiso calc U . R 1 . .
H H21B 0.4937 0.3644 0.295 0.041 Uiso calc U . R 1 . .
H H21C 0.3498 0.392 0.1305 0.041 Uiso calc U . R 1 . .
C C22 0.1008(9) 0.2509(10) -0.0800(8) 0.0271(15) Uani d . . . 1 . .
H H22A 0.0751 0.3222 -0.0817 0.041 Uiso calc U . R 1 . .
H H22B -0.0044 0.2144 -0.1424 0.041 Uiso calc U . R 1 . .
H H22C 0.187 0.2405 -0.1204 0.041 Uiso calc U . R 1 . .
C C23 -0.0235(9) 0.0531(5) 0.0339(9) 0.0196(14) Uani d . . . 1 . .
H H23A -0.11 0.0902 -0.0506 0.029 Uiso calc U . R 1 . .
H H23B -0.077 0.0241 0.0962 0.029 Uiso calc U . R 1 . .
H H23C 0.0241 -0.0003 -0.0059 0.029 Uiso calc U . R 1 . .
Cl Cl1 -0.0849(2) 0.16685(10) 0.36847(19) 0.0130(3) Uani d . . . 1 . .
N N1 0.1275(7) 0.3670(4) 0.4216(6) 0.0104(10) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 C1 . 2.043(6) ?
Ir1 C18 . 2.157(6) ?
Ir1 C17 . 2.168(6) ?
Ir1 C16 . 2.178(5) ?
Ir1 N1 . 2.192(5) ?
Ir1 C14 . 2.263(6) ?
Ir1 C15 . 2.279(6) ?
Ir1 Cl1 . 2.4380(15) ?
C1 C10 . 1.398(8) ?
C1 C2 . 1.416(9) ?
C2 C3 . 1.380(9) ?
C2 H2 . 0.95 ?
C3 C4 . 1.406(9) ?
C3 H3 . 0.95 ?
C4 C5 . 1.424(9) ?
C4 C9 . 1.432(9) ?
C5 C6 . 1.360(9) ?
C5 H5 . 0.95 ?
C6 C7 . 1.406(10) ?
C6 H6 . 0.95 ?
C7 C8 . 1.366(9) ?
C7 H7 . 0.95 ?
C8 C9 . 1.425(9) ?
C8 H8 . 0.95 ?
C9 C10 . 1.423(9) ?
C10 C11 . 1.509(9) ?
C11 N1 . 1.493(8) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 N1 . 1.478(9) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 N1 . 1.487(8) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 C15 . 1.416(9) ?
C14 C18 . 1.456(10) ?
C14 C19 . 1.499(10) ?
C15 C16 . 1.454(11) ?
C15 C20 . 1.494(10) ?
C16 C17 . 1.436(10) ?
C16 C21 . 1.511(12) ?
C17 C18 . 1.462(8) ?
C17 C22 . 1.471(9) ?
C18 C23 . 1.491(9) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Ir1 C18 . . 112.5(3) ?
C1 Ir1 C17 . . 96.9(2) ?
C18 Ir1 C17 . . 39.5(2) ?
C1 Ir1 C16 . . 117.0(3) ?
C18 Ir1 C16 . . 65.1(3) ?
C17 Ir1 C16 . . 38.6(3) ?
C1 Ir1 N1 . . 78.5(2) ?
C18 Ir1 N1 . . 168.1(2) ?
C17 Ir1 N1 . . 137.7(2) ?
C16 Ir1 N1 . . 106.4(3) ?
C1 Ir1 C14 . . 150.3(3) ?
C18 Ir1 C14 . . 38.4(3) ?
C17 Ir1 C14 . . 63.9(2) ?
C16 Ir1 C14 . . 62.8(3) ?
N1 Ir1 C14 . . 131.1(2) ?
C1 Ir1 C15 . . 154.9(2) ?
C18 Ir1 C15 . . 63.7(2) ?
C17 Ir1 C15 . . 63.8(2) ?
C16 Ir1 C15 . . 38.0(3) ?
N1 Ir1 C15 . . 104.4(2) ?
C14 Ir1 C15 . . 36.3(2) ?
C1 Ir1 Cl1 . . 87.82(16) ?
C18 Ir1 Cl1 . . 98.78(17) ?
C17 Ir1 Cl1 . . 136.25(17) ?
C16 Ir1 Cl1 . . 153.8(3) ?
N1 Ir1 Cl1 . . 85.90(14) ?
C14 Ir1 Cl1 . . 91.59(16) ?
C15 Ir1 Cl1 . . 117.10(18) ?
C10 C1 C2 . . 116.8(6) ?
C10 C1 Ir1 . . 117.5(5) ?
C2 C1 Ir1 . . 125.7(5) ?
C3 C2 C1 . . 122.3(6) ?
C3 C2 H2 . . 118.9 ?
C1 C2 H2 . . 118.9 ?
C2 C3 C4 . . 120.9(6) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C3 C4 C5 . . 122.0(6) ?
C3 C4 C9 . . 118.9(6) ?
C5 C4 C9 . . 119.0(6) ?
C6 C5 C4 . . 121.5(7) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 119.6(6) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C8 C7 C6 . . 121.1(6) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C7 C8 C9 . . 121.1(6) ?
C7 C8 H8 . . 119.4 ?
C9 C8 H8 . . 119.4 ?
C10 C9 C8 . . 124.2(6) ?
C10 C9 C4 . . 118.2(5) ?
C8 C9 C4 . . 117.6(6) ?
C1 C10 C9 . . 122.8(6) ?
C1 C10 C11 . . 115.2(5) ?
C9 C10 C11 . . 121.8(5) ?
N1 C11 C10 . . 109.0(5) ?
N1 C11 H11A . . 109.9 ?
C10 C11 H11A . . 109.9 ?
N1 C11 H11B . . 109.9 ?
C10 C11 H11B . . 109.9 ?
H11A C11 H11B . . 108.3 ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C13 H13A . . 109.5 ?
N1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C15 C14 C18 . . 109.3(6) ?
C15 C14 C19 . . 127.5(7) ?
C18 C14 C19 . . 123.2(6) ?
C15 C14 Ir1 . . 72.4(4) ?
C18 C14 Ir1 . . 66.9(3) ?
C19 C14 Ir1 . . 126.1(5) ?
C14 C15 C16 . . 107.4(6) ?
C14 C15 C20 . . 127.9(6) ?
C16 C15 C20 . . 124.5(6) ?
C14 C15 Ir1 . . 71.2(4) ?
C16 C15 Ir1 . . 67.2(3) ?
C20 C15 Ir1 . . 130.0(5) ?
C17 C16 C15 . . 109.0(8) ?
C17 C16 C21 . . 124.5(7) ?
C15 C16 C21 . . 124.9(6) ?
C17 C16 Ir1 . . 70.3(3) ?
C15 C16 Ir1 . . 74.8(4) ?
C21 C16 Ir1 . . 132.7(7) ?
C16 C17 C18 . . 107.1(7) ?
C16 C17 C22 . . 125.8(7) ?
C18 C17 C22 . . 126.4(7) ?
C16 C17 Ir1 . . 71.1(3) ?
C18 C17 Ir1 . . 69.8(4) ?
C22 C17 Ir1 . . 131.4(5) ?
C14 C18 C17 . . 107.0(6) ?
C14 C18 C23 . . 126.2(6) ?
C17 C18 C23 . . 126.4(7) ?
C14 C18 Ir1 . . 74.8(4) ?
C17 C18 Ir1 . . 70.6(3) ?
C23 C18 Ir1 . . 126.2(4) ?
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 ?
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 ?
C12 N1 C13 . . 108.3(5) ?
C12 N1 C11 . . 108.5(5) ?
C13 N1 C11 . . 107.5(5) ?
C12 N1 Ir1 . . 113.3(4) ?
C13 N1 Ir1 . . 110.3(4) ?
C11 N1 Ir1 . . 108.8(4) ?

####################################################################### 
# 
# 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_leung1045m
_database_code_depnum_ccdc_archive 'CCDC 1830655'
_audit_update_record             
;
2018-03-18 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Cl Ir'
_chemical_formula_iupac          ?
_chemical_formula_weight         516.06
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.0801(5)
_cell_length_b                   7.2442(2)
_cell_length_c                   14.5460(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1799.80(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8327
_cell_measurement_theta_min      2.7658
_cell_measurement_theta_max      35.3644
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000

_exptl_absorpt_coefficient_mu    7.567
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.66

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            26362
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         34.00
_diffrn_reflns_theta_full        34.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             7323
_reflns_number_gt                5966
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0604
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_number_reflns         7323
_refine_ls_number_parameters     223
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.6661P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.934
_refine_diff_density_min         -1.385
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.094(12)

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3666(4) -0.0229(8) 0.5517(5) 0.0133(12) Uani d . . . 1 . .
C C2 0.3458(4) -0.0228(9) 0.6423(5) 0.0162(13) Uani d . . . 1 . .
H H2 0.380326 0.02807 0.686753 0.019 Uiso calc U . R 1 . .
C C3 0.2734(6) -0.0973(11) 0.6706(7) 0.0185(18) Uani d . . . 1 . .
H H3 0.260096 -0.094493 0.733974 0.022 Uiso calc U . R 1 . .
C C4 0.2219(4) -0.1731(10) 0.6100(6) 0.0196(16) Uani d . . . 1 . .
H H4 0.174446 -0.225899 0.631513 0.024 Uiso calc U . R 1 . .
C C5 0.2391(4) -0.1732(8) 0.5150(5) 0.0178(19) Uani d . . . 1 . .
C C6 0.3128(3) -0.1002(7) 0.4876(9) 0.0132(17) Uani d . . . 1 . .
C C7 0.3336(4) -0.0951(9) 0.3940(5) 0.0167(12) Uani d . . . 1 . .
C C8 0.2810(5) -0.1494(11) 0.3273(7) 0.0171(18) Uani d . . . 1 . .
H H8 0.2937 -0.141166 0.263833 0.021 Uiso calc U . R 1 . .
C C9 0.2077(5) -0.2176(10) 0.3563(6) 0.0211(16) Uani d . . . 1 . .
H H9 0.170945 -0.2554 0.310977 0.025 Uiso calc U . R 1 . .
C C10 0.1874(4) -0.2315(10) 0.4463(5) 0.0223(15) Uani d . . . 1 . .
H H10 0.137845 -0.281156 0.462657 0.027 Uiso calc U . R 1 . .
C C11 0.4153(4) -0.0388(9) 0.3754(5) 0.0165(13) Uani d . . . 1 . .
H H11 0.424607 0.072141 0.342271 0.02 Uiso calc U . R 1 . .
C C12 0.4796(4) -0.1443(10) 0.4052(5) 0.0186(14) Uani d . . . 1 . .
H H12A 0.471255 -0.255491 0.438321 0.022 Uiso calc U . R 1 . .
H H12B 0.531394 -0.104257 0.392095 0.022 Uiso calc U . R 1 . .
C C13 0.5280(6) 0.3007(12) 0.4165(8) 0.0168(18) Uani d . . . 1 . .
C C14 0.4489(5) 0.3546(11) 0.4357(5) 0.0142(15) Uani d . . . 1 . .
C C15 0.4409(5) 0.3786(10) 0.5314(5) 0.0126(14) Uani d . . . 1 . .
C C16 0.5138(6) 0.3326(12) 0.5727(7) 0.0173(19) Uani d . . . 1 . .
C C17 0.5685(3) 0.2849(6) 0.5002(11) 0.0164(11) Uani d . . . 1 . .
C C18 0.6524(4) 0.2306(10) 0.5171(6) 0.025(2) Uani d . . . 1 . .
H H18A 0.676447 0.191996 0.459008 0.038 Uiso calc U . R 1 . .
H H18B 0.654121 0.128184 0.561022 0.038 Uiso calc U . R 1 . .
H H18C 0.681134 0.336289 0.542134 0.038 Uiso calc U . R 1 . .
C C19 0.5657(6) 0.2823(11) 0.3238(6) 0.0265(18) Uani d . . . 1 . .
H H19A 0.588439 0.401096 0.305702 0.04 Uiso calc U . R 1 . .
H H19B 0.526214 0.245217 0.278516 0.04 Uiso calc U . R 1 . .
H H19C 0.607021 0.188659 0.326556 0.04 Uiso calc U . R 1 . .
C C20 0.3862(5) 0.4007(11) 0.3667(6) 0.0258(16) Uani d . . . 1 . .
H H20A 0.335208 0.361101 0.390347 0.039 Uiso calc U . R 1 . .
H H20B 0.397174 0.336656 0.308728 0.039 Uiso calc U . R 1 . .
H H20C 0.385515 0.534236 0.355997 0.039 Uiso calc U . R 1 . .
C C21 0.3708(5) 0.4472(10) 0.5824(6) 0.0249(16) Uani d . . . 1 . .
H H21A 0.363062 0.372489 0.637817 0.037 Uiso calc U . R 1 . .
H H21B 0.324477 0.437641 0.542957 0.037 Uiso calc U . R 1 . .
H H21C 0.378953 0.576412 0.599844 0.037 Uiso calc U . R 1 . .
C C22 0.5340(6) 0.3389(12) 0.6734(6) 0.0281(18) Uani d . . . 1 . .
H H22A 0.485813 0.347662 0.709641 0.042 Uiso calc U . R 1 . .
H H22B 0.567025 0.446745 0.685648 0.042 Uiso calc U . R 1 . .
H H22C 0.562364 0.226308 0.690357 0.042 Uiso calc U . R 1 . .
Cl Cl1 0.53014(10) -0.1149(2) 0.60761(12) 0.0189(3) Uani d . . . 1 . .
Ir Ir1 0.46769(2) 0.08326(2) 0.49701(3) 0.01113(5) Uani d . . . 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.365(9) ?
C1 C6 . 1.425(11) ?
C1 Ir1 . 2.050(6) ?
C2 C3 . 1.410(12) ?
C2 H2 . 0.95 ?
C3 C4 . 1.360(13) ?
C3 H3 . 0.95 ?
C4 C5 . 1.412(11) ?
C4 H4 . 0.95 ?
C5 C10 . 1.399(10) ?
C5 C6 . 1.422(9) ?
C6 C7 . 1.409(14) ?
C7 C8 . 1.380(11) ?
C7 C11 . 1.479(10) ?
C8 C9 . 1.411(12) ?
C8 H8 . 0.95 ?
C9 C10 . 1.357(11) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 C12 . 1.407(10) ?
C11 Ir1 . 2.171(7) ?
C11 H11 . 0.95 ?
C12 Ir1 . 2.131(7) ?
C12 H12A . 0.95 ?
C12 H12B . 0.95 ?
C13 C17 . 1.405(17) ?
C13 C14 . 1.434(12) ?
C13 C19 . 1.500(13) ?
C13 Ir1 . 2.217(9) ?
C14 C15 . 1.410(11) ?
C14 C20 . 1.505(11) ?
C14 Ir1 . 2.182(8) ?
C15 C16 . 1.423(13) ?
C15 C21 . 1.492(11) ?
C15 Ir1 . 2.244(8) ?
C16 C17 . 1.451(16) ?
C16 C22 . 1.505(13) ?
C16 Ir1 . 2.257(10) ?
C17 C18 . 1.506(9) ?
C17 Ir1 . 2.259(5) ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
Cl1 Ir1 . 2.4057(16) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 117.6(7) ?
C2 C1 Ir1 . . 126.5(5) ?
C6 C1 Ir1 . . 115.9(6) ?
C1 C2 C3 . . 120.7(8) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C4 C3 C2 . . 122.1(9) ?
C4 C3 H3 . . 118.9 ?
C2 C3 H3 . . 118.9 ?
C3 C4 C5 . . 120.0(7) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C10 C5 C4 . . 124.6(6) ?
C10 C5 C6 . . 118.1(8) ?
C4 C5 C6 . . 117.2(7) ?
C7 C6 C5 . . 120.3(8) ?
C7 C6 C1 . . 117.4(6) ?
C5 C6 C1 . . 122.3(10) ?
C8 C7 C6 . . 120.5(7) ?
C8 C7 C11 . . 124.4(7) ?
C6 C7 C11 . . 115.0(6) ?
C7 C8 C9 . . 117.9(9) ?
C7 C8 H8 . . 121.1 ?
C9 C8 H8 . . 121.1 ?
C10 C9 C8 . . 122.7(8) ?
C10 C9 H9 . . 118.6 ?
C8 C9 H9 . . 118.6 ?
C9 C10 C5 . . 120.4(7) ?
C9 C10 H10 . . 119.8 ?
C5 C10 H10 . . 119.8 ?
C12 C11 C7 . . 122.1(6) ?
C12 C11 Ir1 . . 69.4(4) ?
C7 C11 Ir1 . . 110.6(5) ?
C12 C11 H11 . . 119.0 ?
C7 C11 H11 . . 119.0 ?
Ir1 C11 H11 . . 90.0 ?
C11 C12 Ir1 . . 72.4(4) ?
C11 C12 H12A . . 120.0 ?
Ir1 C12 H12A . . 108.9 ?
C11 C12 H12B . . 120.0 ?
Ir1 C12 H12B . . 88.8 ?
H12A C12 H12B . . 120.0 ?
C17 C13 C14 . . 108.5(9) ?
C17 C13 C19 . . 124.1(9) ?
C14 C13 C19 . . 127.1(9) ?
C17 C13 Ir1 . . 73.3(5) ?
C14 C13 Ir1 . . 69.7(5) ?
C19 C13 Ir1 . . 127.7(6) ?
C15 C14 C13 . . 108.5(9) ?
C15 C14 C20 . . 124.2(8) ?
C13 C14 C20 . . 126.9(8) ?
C15 C14 Ir1 . . 73.8(5) ?
C13 C14 Ir1 . . 72.3(5) ?
C20 C14 Ir1 . . 125.2(6) ?
C14 C15 C16 . . 107.6(9) ?
C14 C15 C21 . . 127.6(8) ?
C16 C15 C21 . . 124.8(8) ?
C14 C15 Ir1 . . 69.1(6) ?
C16 C15 Ir1 . . 72.1(5) ?
C21 C15 Ir1 . . 126.3(6) ?
C15 C16 C17 . . 108.2(9) ?
C15 C16 C22 . . 127.2(9) ?
C17 C16 C22 . . 124.6(9) ?
C15 C16 Ir1 . . 71.1(5) ?
C17 C16 Ir1 . . 71.3(5) ?
C22 C16 Ir1 . . 125.4(6) ?
C13 C17 C16 . . 107.1(6) ?
C13 C17 C18 . . 129.1(11) ?
C16 C17 C18 . . 123.8(12) ?
C13 C17 Ir1 . . 70.1(4) ?
C16 C17 Ir1 . . 71.2(5) ?
C18 C17 Ir1 . . 124.0(4) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C13 C19 H19A . . 109.5 ?
C13 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C13 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C14 C20 H20A . . 109.5 ?
C14 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C14 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C15 C21 H21A . . 109.5 ?
C15 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C15 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C16 C22 H22A . . 109.5 ?
C16 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C16 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C1 Ir1 C12 . . 91.9(3) ?
C1 Ir1 C11 . . 79.4(3) ?
C12 Ir1 C11 . . 38.2(3) ?
C1 Ir1 C14 . . 111.9(3) ?
C12 Ir1 C14 . . 117.0(3) ?
C11 Ir1 C14 . . 88.5(3) ?
C1 Ir1 C13 . . 149.6(3) ?
C12 Ir1 C13 . . 100.0(3) ?
C11 Ir1 C13 . . 92.9(3) ?
C14 Ir1 C13 . . 38.0(3) ?
C1 Ir1 C15 . . 95.7(3) ?
C12 Ir1 C15 . . 153.7(3) ?
C11 Ir1 C15 . . 119.1(3) ?
C14 Ir1 C15 . . 37.1(3) ?
C13 Ir1 C15 . . 62.3(3) ?
C1 Ir1 C16 . . 113.9(3) ?
C12 Ir1 C16 . . 153.0(3) ?
C11 Ir1 C16 . . 150.1(3) ?
C14 Ir1 C16 . . 62.0(3) ?
C13 Ir1 C16 . . 61.8(2) ?
C15 Ir1 C16 . . 36.9(3) ?
C1 Ir1 C17 . . 151.2(4) ?
C12 Ir1 C17 . . 116.1(4) ?
C11 Ir1 C17 . . 126.5(4) ?
C14 Ir1 C17 . . 62.5(3) ?
C13 Ir1 C17 . . 36.6(5) ?
C15 Ir1 C17 . . 62.3(3) ?
C16 Ir1 C17 . . 37.5(4) ?
C1 Ir1 Cl1 . . 83.66(18) ?
C12 Ir1 Cl1 . . 85.1(2) ?
C11 Ir1 Cl1 . . 119.00(18) ?
C14 Ir1 Cl1 . . 151.2(2) ?
C13 Ir1 Cl1 . . 124.8(3) ?
C15 Ir1 Cl1 . . 120.7(2) ?
C16 Ir1 Cl1 . . 89.8(2) ?
C17 Ir1 Cl1 . . 92.0(3) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane, Dichloromethane'
