# 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_miao1
_database_code_depnum_ccdc_archive 'CCDC 1544033'
_audit_update_record             
;
2018-09-02 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;
_audit_creation_date             2018-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H30 Cl Ir N2 O, C H2 Cl2'
_chemical_formula_sum            'C24 H32 Cl3 Ir N2 O'
_chemical_formula_weight         663.06
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2934(19)
_cell_length_b                   11.622(2)
_cell_length_c                   13.674(3)
_cell_angle_alpha                65.73(3)
_cell_angle_beta                 80.57(3)
_cell_angle_gamma                74.82(3)
_cell_volume                     1296.8(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6371
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      1.64
_shelx_estimated_absorpt_T_max   0.584
_shelx_estimated_absorpt_T_min   0.514
_exptl_absorpt_coefficient_mu    5.475
_exptl_absorpt_correction_T_max  0.335
_exptl_absorpt_correction_T_min  0.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9851
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_min         1.637
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5325
_reflns_number_total             6371
_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.
 The residual peaks are associated with the heavy element.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         3.056
_refine_diff_density_min         -1.937
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0709P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1213
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C23(0.5) H23A(0.5) H23B(0.5) C24(0.5) H24A(0.5) H24B(0.5)
 H24C(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5) C26(0.5) H23C(0.5) H26(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C22(H22A,H22B), C23(H23A,H23B), C26(H23C,H26)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.72771(2) -0.03190(2) 0.73351(2) 0.03838(10) Uani 1 1 d . . . . .
Cl1 Cl 0.46856(18) -0.02315(19) 0.72149(13) 0.0526(4) Uani 1 1 d . . . . .
O1 O 0.7144(5) -0.1943(4) 0.8760(3) 0.0438(10) Uani 1 1 d . . . . .
N1 N 0.7020(7) 0.0098(6) 0.9371(5) 0.0486(13) Uani 1 1 d . . . . .
N2 N 0.5751(7) 0.1779(6) 0.8221(5) 0.0554(15) Uani 1 1 d . . . . .
C1 C 0.6643(8) 0.0615(7) 0.8348(5) 0.0469(15) Uani 1 1 d . . . . .
C2 C 0.9206(7) -0.1355(7) 0.6606(5) 0.0474(15) Uani 1 1 d . . . . .
C3 C 0.8013(7) -0.2118(7) 0.9509(5) 0.0439(14) Uani 1 1 d . . . . .
C4 C 0.7817(8) 0.0661(7) 0.5644(5) 0.0496(16) Uani 1 1 d . . . . .
C5 C 0.6807(11) 0.1713(9) 0.4812(6) 0.071(2) Uani 1 1 d . . . . .
H5A H 0.715694 0.170071 0.411516 0.106 Uiso 1 1 calc GR . . . .
H5B H 0.681211 0.253708 0.481302 0.106 Uiso 1 1 calc GR . . . .
H5C H 0.580778 0.156953 0.497908 0.106 Uiso 1 1 calc GR . . . .
C6 C 0.8024(8) -0.1132(7) 0.9831(5) 0.0466(15) Uani 1 1 d . . . . .
C7 C 0.8111(7) -0.0691(7) 0.5844(5) 0.0461(15) Uani 1 1 d . . . . .
C8 C 0.9597(8) -0.0424(8) 0.6903(6) 0.0525(17) Uani 1 1 d . . . . .
C9 C 0.8787(8) 0.0819(8) 0.6276(6) 0.0534(17) Uani 1 1 d . . . . .
C10 C 0.5108(10) 0.2723(8) 0.7225(7) 0.067(2) Uani 1 1 d . . . . .
H10A H 0.536994 0.235266 0.668386 0.080 Uiso 1 1 calc R . . . .
H10B H 0.555004 0.347211 0.697913 0.080 Uiso 1 1 calc R . . . .
C11 C 0.8997(10) -0.1301(9) 1.0579(6) 0.064(2) Uani 1 1 d . . . . .
H11 H 0.899798 -0.062255 1.077257 0.077 Uiso 1 1 calc R . . . .
C12 C 0.5587(10) 0.1976(8) 0.9173(6) 0.065(2) Uani 1 1 d . . . . .
H12 H 0.503035 0.270713 0.928653 0.077 Uiso 1 1 calc R . . . .
Cl2 Cl 0.6414(7) 0.5485(5) 0.7533(5) 0.177(2) Uani 1 1 d . . . . .
Cl3 Cl 0.3669(6) 0.5908(6) 0.8763(6) 0.191(3) Uani 1 1 d . . . . .
C13 C 0.6360(10) 0.0943(8) 0.9882(6) 0.0595(19) Uani 1 1 d . . . . .
H13 H 0.645102 0.080054 1.059200 0.071 Uiso 1 1 calc R . . . .
C14 C 0.8939(9) -0.3306(8) 1.0029(6) 0.0613(19) Uani 1 1 d . . . . .
H14 H 0.891659 -0.400267 0.986588 0.074 Uiso 1 1 calc R . . . .
C15 C 0.7333(10) -0.1278(9) 0.5340(6) 0.067(2) Uani 1 1 d . . . . .
H15A H 0.761725 -0.099948 0.458453 0.100 Uiso 1 1 calc GR . . . .
H15B H 0.627080 -0.100383 0.544172 0.100 Uiso 1 1 calc GR . . . .
H15C H 0.761440 -0.220313 0.567160 0.100 Uiso 1 1 calc GR . . . .
C16 C 1.0825(9) -0.0706(10) 0.7624(7) 0.071(2) Uani 1 1 d . . . . .
H16A H 1.177854 -0.090102 0.726500 0.107 Uiso 1 1 calc GR . . . .
H16B H 1.071046 -0.143138 0.828012 0.107 Uiso 1 1 calc GR . . . .
H16C H 1.076474 0.003714 0.778338 0.107 Uiso 1 1 calc GR . . . .
C17 C 0.9770(10) -0.2788(8) 0.7096(7) 0.067(2) Uani 1 1 d . . . . .
H17A H 0.894248 -0.320779 0.729835 0.101 Uiso 1 1 calc GR . . . .
H17B H 1.029122 -0.300956 0.772153 0.101 Uiso 1 1 calc GR . . . .
H17C H 1.043816 -0.306696 0.658308 0.101 Uiso 1 1 calc GR . . . .
C18 C 0.8991(12) 0.2074(9) 0.6234(8) 0.082(3) Uani 1 1 d . . . . .
H18A H 0.899979 0.202277 0.695220 0.123 Uiso 1 1 calc GR . . . .
H18B H 0.818352 0.275849 0.587783 0.123 Uiso 1 1 calc GR . . . .
H18C H 0.992087 0.224722 0.584588 0.123 Uiso 1 1 calc GR . . . .
C19 C 0.9944(11) -0.2467(11) 1.1024(7) 0.080(3) Uani 1 1 d . . . . .
H19 H 1.062873 -0.257441 1.149670 0.096 Uiso 1 1 calc R . . . .
C20 C 0.9888(10) -0.3487(10) 1.0775(7) 0.075(2) Uani 1 1 d . . . . .
H20 H 1.049170 -0.429775 1.111072 0.090 Uiso 1 1 calc R . . . .
C21 C 0.3472(14) 0.3151(14) 0.7317(11) 0.104(4) Uani 1 1 d . . . . .
C22 C 0.5350(18) 0.6328(15) 0.8281(15) 0.139(6) Uani 1 1 d . . . . .
H22A H 0.590420 0.617427 0.888130 0.166 Uiso 1 1 calc R . . . .
H22B H 0.517783 0.724562 0.783825 0.166 Uiso 1 1 calc R . . . .
C23 C 0.304(5) 0.395(5) 0.608(4) 0.17(3) Uani 0.5 1 d . . P . .
H23A H 0.347722 0.470690 0.578111 0.204 Uiso 0.5 1 calc R . P . .
H23B H 0.347810 0.341525 0.567622 0.204 Uiso 0.5 1 calc R . P . .
C24 C 0.275(3) 0.397(3) 0.556(3) 0.114(11) Uani 0.5 1 d . . P . .
H24A H 0.374060 0.385827 0.522579 0.171 Uiso 0.5 1 calc GR . P . .
H24B H 0.208658 0.463672 0.503697 0.171 Uiso 0.5 1 calc GR . P . .
H24C H 0.241475 0.317595 0.581525 0.171 Uiso 0.5 1 calc GR . P . .
C25 C 0.139(5) 0.439(3) 0.594(3) 0.171(18) Uani 0.5 1 d . . P . .
H25A H 0.104224 0.374824 0.581770 0.257 Uiso 0.5 1 calc GR . P . .
H25B H 0.119105 0.519404 0.533006 0.257 Uiso 0.5 1 calc GR . P . .
H25C H 0.087014 0.449729 0.657170 0.257 Uiso 0.5 1 calc GR . P . .
C26 C 0.275(5) 0.432(3) 0.640(3) 0.101(12) Uani 0.5 1 d . . P . .
H23C H 0.173279 0.464692 0.662154 0.122 Uiso 0.5 1 calc R . P . .
H26 H 0.329993 0.500009 0.618189 0.122 Uiso 0.5 1 calc R . P . .
H21A H 0.301(15) 0.248(12) 0.747(11) 0.122 Uiso 1 1 d R . . . .
H21B H 0.312(16) 0.342(14) 0.777(11) 0.122 Uiso 1 1 d R . . . .


_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 Cl1 2.4136(17) . ?
Ir1 O1 2.096(5) . ?
Ir1 C1 2.019(6) . ?
Ir1 C2 2.220(6) . ?
Ir1 C4 2.156(6) . ?
Ir1 C7 2.230(6) . ?
Ir1 C8 2.125(7) . ?
Ir1 C9 2.133(7) . ?
O1 C3 1.326(8) . ?
N1 C1 1.342(9) . ?
N1 C6 1.436(9) . ?
N1 C13 1.391(9) . ?
N2 C1 1.347(9) . ?
N2 C10 1.452(10) . ?
N2 C12 1.391(9) . ?
C2 C7 1.411(10) . ?
C2 C8 1.443(10) . ?
C2 C17 1.496(11) . ?
C3 C6 1.390(9) . ?
C3 C14 1.387(10) . ?
C4 C5 1.509(11) . ?
C4 C7 1.436(10) . ?
C4 C9 1.437(10) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C11 1.395(10) . ?
C7 C15 1.508(10) . ?
C8 C9 1.419(11) . ?
C8 C16 1.512(10) . ?
C9 C18 1.498(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C21 1.472(15) . ?
C11 H11 0.9300 . ?
C11 C19 1.362(13) . ?
C12 H12 0.9300 . ?
C12 C13 1.311(12) . ?
Cl2 C22 1.723(17) . ?
Cl3 C22 1.706(16) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C20 1.372(11) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.377(13) . ?
C20 H20 0.9300 . ?
C21 C23 1.62(5) . ?
C21 C26 1.51(4) . ?
C21 H21A 0.92(13) . ?
C21 H21B 0.79(13) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C25 1.50(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 C26 1.37(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H23C 0.9700 . ?
C26 H26 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ir1 Cl1 85.28(13) . . ?
O1 Ir1 C2 94.1(2) . . ?
O1 Ir1 C4 154.7(2) . . ?
O1 Ir1 C7 116.6(2) . . ?
O1 Ir1 C8 105.5(3) . . ?
O1 Ir1 C9 143.0(3) . . ?
C1 Ir1 Cl1 89.3(2) . . ?
C1 Ir1 O1 82.4(2) . . ?
C1 Ir1 C2 145.1(3) . . ?
C1 Ir1 C4 122.5(3) . . ?
C1 Ir1 C7 160.5(3) . . ?
C1 Ir1 C8 108.7(3) . . ?
C1 Ir1 C9 98.5(3) . . ?
C2 Ir1 Cl1 125.15(19) . . ?
C2 Ir1 C7 37.0(3) . . ?
C4 Ir1 Cl1 97.6(2) . . ?
C4 Ir1 C2 63.6(3) . . ?
C4 Ir1 C7 38.2(3) . . ?
C7 Ir1 Cl1 95.92(18) . . ?
C8 Ir1 Cl1 159.8(2) . . ?
C8 Ir1 C2 38.7(3) . . ?
C8 Ir1 C4 65.4(3) . . ?
C8 Ir1 C7 64.1(3) . . ?
C8 Ir1 C9 38.9(3) . . ?
C9 Ir1 Cl1 131.6(2) . . ?
C9 Ir1 C2 64.1(3) . . ?
C9 Ir1 C4 39.1(3) . . ?
C9 Ir1 C7 64.1(3) . . ?
C3 O1 Ir1 114.8(4) . . ?
C1 N1 C6 123.4(6) . . ?
C1 N1 C13 110.4(7) . . ?
C13 N1 C6 126.1(6) . . ?
C1 N2 C10 125.4(6) . . ?
C1 N2 C12 110.0(6) . . ?
C12 N2 C10 124.5(7) . . ?
N1 C1 Ir1 123.6(5) . . ?
N1 C1 N2 105.1(6) . . ?
N2 C1 Ir1 131.2(5) . . ?
C7 C2 Ir1 71.9(4) . . ?
C7 C2 C8 108.2(7) . . ?
C7 C2 C17 126.0(7) . . ?
C8 C2 Ir1 67.1(4) . . ?
C8 C2 C17 125.5(7) . . ?
C17 C2 Ir1 122.7(5) . . ?
O1 C3 C6 121.9(6) . . ?
O1 C3 C14 121.6(6) . . ?
C14 C3 C6 116.4(6) . . ?
C5 C4 Ir1 127.9(5) . . ?
C7 C4 Ir1 73.7(4) . . ?
C7 C4 C5 124.8(7) . . ?
C7 C4 C9 107.5(6) . . ?
C9 C4 Ir1 69.5(4) . . ?
C9 C4 C5 127.3(7) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 N1 119.1(6) . . ?
C3 C6 C11 121.7(7) . . ?
C11 C6 N1 119.3(6) . . ?
C2 C7 Ir1 71.1(4) . . ?
C2 C7 C4 108.3(6) . . ?
C2 C7 C15 126.8(7) . . ?
C4 C7 Ir1 68.1(4) . . ?
C4 C7 C15 124.9(7) . . ?
C15 C7 Ir1 125.1(5) . . ?
C2 C8 Ir1 74.2(4) . . ?
C2 C8 C16 125.6(8) . . ?
C9 C8 Ir1 70.8(4) . . ?
C9 C8 C2 107.7(6) . . ?
C9 C8 C16 126.0(7) . . ?
C16 C8 Ir1 127.7(5) . . ?
C4 C9 Ir1 71.3(4) . . ?
C4 C9 C18 126.4(8) . . ?
C8 C9 Ir1 70.2(4) . . ?
C8 C9 C4 108.2(6) . . ?
C8 C9 C18 125.4(8) . . ?
C18 C9 Ir1 127.0(5) . . ?
N2 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
N2 C10 C21 114.1(8) . . ?
H10A C10 H10B 107.6 . . ?
C21 C10 H10A 108.7 . . ?
C21 C10 H10B 108.7 . . ?
C6 C11 H11 120.2 . . ?
C19 C11 C6 119.6(8) . . ?
C19 C11 H11 120.2 . . ?
N2 C12 H12 126.3 . . ?
C13 C12 N2 107.4(7) . . ?
C13 C12 H12 126.3 . . ?
N1 C13 H13 126.5 . . ?
C12 C13 N1 107.0(7) . . ?
C12 C13 H13 126.5 . . ?
C3 C14 H14 118.9 . . ?
C20 C14 C3 122.2(8) . . ?
C20 C14 H14 118.9 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C17 H17A 109.5 . . ?
C2 C17 H17B 109.5 . . ?
C2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 H19 120.0 . . ?
C11 C19 C20 120.0(8) . . ?
C20 C19 H19 120.0 . . ?
C14 C20 C19 119.8(8) . . ?
C14 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C10 C21 C23 103.5(19) . . ?
C10 C21 C26 117.5(19) . . ?
C10 C21 H21A 111(9) . . ?
C10 C21 H21B 118(10) . . ?
C23 C21 H21A 97(9) . . ?
C23 C21 H21B 121(10) . . ?
C26 C21 C23 26(2) . . ?
C26 C21 H21A 109(9) . . ?
C26 C21 H21B 96(10) . . ?
H21A C21 H21B 104(10) . . ?
Cl2 C22 H22A 108.9 . . ?
Cl2 C22 H22B 108.9 . . ?
Cl3 C22 Cl2 113.2(7) . . ?
Cl3 C22 H22A 108.9 . . ?
Cl3 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
C21 C23 H23A 108.6 . . ?
C21 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C25 C23 C21 114(4) . . ?
C25 C23 H23A 108.6 . . ?
C25 C23 H23B 108.6 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C24 H24A 109.5 . . ?
C26 C24 H24B 109.5 . . ?
C26 C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C21 C26 H23C 110.0 . . ?
C21 C26 H26 110.0 . . ?
C24 C26 C21 109(2) . . ?
C24 C26 H23C 110.0 . . ?
C24 C26 H26 110.0 . . ?
H23C C26 H26 108.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_170921e
_database_code_depnum_ccdc_archive 'CCDC 1852809'
_audit_update_record             
;
2018-09-01 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H36 Cl Ir N2 O'
_chemical_formula_weight         800.37

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/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                   10.2202(9)
_cell_length_b                   15.4052(13)
_cell_length_c                   21.1662(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.9780(10)
_cell_angle_gamma                90
_cell_volume                     3314.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5608
_cell_measurement_theta_min      2.344
_cell_measurement_theta_max      25.796

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             1592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    4.145
_shelx_estimated_absorpt_T_min   0.369
_shelx_estimated_absorpt_T_max   0.595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3329
_exptl_absorpt_correction_T_max  0.7388
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16304
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.343
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_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             5827
_reflns_number_gt                4210
_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.
 The residual peaks are associated with the heavy element.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5827
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.31405(2) 0.31072(2) 0.23940(2) 0.03130(12) Uani 1 1 d . . . . .
Cl1 Cl 0.52203(18) 0.25340(12) 0.21485(10) 0.0472(5) Uani 1 1 d . . . . .
N1 N 0.3994(6) 0.3070(3) 0.3784(3) 0.0318(14) Uani 1 1 d . . . . .
N2 N 0.3918(6) 0.1750(3) 0.3422(3) 0.0378(15) Uani 1 1 d . . . . .
O1 O 0.4304(5) 0.4151(3) 0.2766(3) 0.0423(13) Uani 1 1 d . . . . .
C1 C 0.3636(6) 0.2587(4) 0.3252(3) 0.0309(16) Uani 1 1 d . . . . .
C2 C 0.4561(7) 0.1711(5) 0.4040(4) 0.0386(18) Uani 1 1 d . . . . .
C3 C 0.4608(6) 0.2555(5) 0.4274(4) 0.0359(17) Uani 1 1 d . . . . .
C4 C 0.5249(8) 0.2741(5) 0.4854(4) 0.047(2) Uani 1 1 d . . . . .
H4 H 0.5284 0.3305 0.5013 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5844(8) 0.2065(5) 0.5196(4) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.6300 0.2176 0.5592 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5779(8) 0.1218(5) 0.4964(4) 0.052(2) Uani 1 1 d . . . . .
H6 H 0.6190 0.0775 0.5209 0.063 Uiso 1 1 calc R U . . .
C7 C 0.5124(7) 0.1022(5) 0.4385(4) 0.045(2) Uani 1 1 d . . . . .
H7 H 0.5063 0.0456 0.4232 0.054 Uiso 1 1 calc R U . . .
C8 C 0.3773(7) 0.3989(4) 0.3825(4) 0.0355(18) Uani 1 1 d . . . . .
C9 C 0.3948(6) 0.4498(5) 0.3297(4) 0.0347(17) Uani 1 1 d . . . . .
C10 C 0.3744(7) 0.5395(5) 0.3347(4) 0.045(2) Uani 1 1 d . . . . .
H10 H 0.3853 0.5755 0.3003 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3390(7) 0.5743(5) 0.3894(4) 0.049(2) Uani 1 1 d . . . . .
H11 H 0.3289 0.6341 0.3922 0.059 Uiso 1 1 calc R U . . .
C12 C 0.3176(7) 0.5238(5) 0.4408(4) 0.047(2) Uani 1 1 d . . . . .
H12 H 0.2902 0.5487 0.4772 0.056 Uiso 1 1 calc R U . . .
C13 C 0.3379(7) 0.4348(5) 0.4374(4) 0.0442(19) Uani 1 1 d . . . . .
H13 H 0.3250 0.3995 0.4718 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3669(8) 0.0989(5) 0.3032(4) 0.048(2) Uani 1 1 d . . . . .
H14A H 0.4504 0.0725 0.2961 0.058 Uiso 1 1 calc R U . . .
H14B H 0.3239 0.1164 0.2622 0.058 Uiso 1 1 calc R U . . .
C15 C 0.2824(7) 0.0318(4) 0.3317(3) 0.0361(17) Uani 1 1 d . . . . .
C16 C 0.1934(7) 0.0534(5) 0.3739(4) 0.050(2) Uani 1 1 d . . . . .
H16 H 0.1821 0.1111 0.3849 0.060 Uiso 1 1 calc R U . . .
C17 C 0.1208(8) -0.0113(6) 0.3997(4) 0.060(2) Uani 1 1 d . . . . .
H17 H 0.0618 0.0028 0.4287 0.072 Uiso 1 1 calc R U . . .
C18 C 0.1364(9) -0.0969(6) 0.3820(5) 0.063(3) Uani 1 1 d . . . . .
H18 H 0.0867 -0.1403 0.3985 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2233(8) -0.1171(5) 0.3412(4) 0.056(2) Uani 1 1 d . . . . .
H19 H 0.2337 -0.1748 0.3299 0.067 Uiso 1 1 calc R U . . .
C20 C 0.2974(8) -0.0544(5) 0.3155(4) 0.048(2) Uani 1 1 d . . . . .
H20 H 0.3574 -0.0699 0.2874 0.057 Uiso 1 1 calc R U . . .
C21 C 0.1730(6) 0.2485(5) 0.1706(3) 0.0342(17) Uani 1 1 d . . . . .
C22 C 0.1101(7) 0.2778(5) 0.2237(4) 0.0385(18) Uani 1 1 d . . . . .
C23 C 0.1245(7) 0.3699(5) 0.2276(4) 0.0399(18) Uani 1 1 d . . . . .
C24 C 0.1907(7) 0.3976(5) 0.1741(4) 0.0384(18) Uani 1 1 d . . . . .
C25 C 0.2231(7) 0.3245(5) 0.1405(4) 0.0372(18) Uani 1 1 d . . . . .
C26 C 0.1687(7) 0.1575(5) 0.1441(3) 0.0381(18) Uani 1 1 d . . . . .
C27 C 0.2814(7) 0.1098(5) 0.1365(4) 0.048(2) Uani 1 1 d . . . . .
H27 H 0.3634 0.1363 0.1437 0.057 Uiso 1 1 calc R U . . .
C28 C 0.2738(7) 0.0245(5) 0.1185(4) 0.049(2) Uani 1 1 d . . . . .
H28 H 0.3508 -0.0065 0.1152 0.058 Uiso 1 1 calc R U . . .
C29 C 0.1534(7) -0.0163(5) 0.1052(4) 0.0384(18) Uani 1 1 d . . . . .
C30 C 0.0411(7) 0.0335(5) 0.1078(4) 0.044(2) Uani 1 1 d . . . . .
H30 H -0.0406 0.0086 0.0958 0.053 Uiso 1 1 calc R U . . .
C31 C 0.0469(7) 0.1188(5) 0.1279(4) 0.0424(19) Uani 1 1 d . . . . .
H31 H -0.0301 0.1501 0.1304 0.051 Uiso 1 1 calc R U . . .
C32 C 0.1441(8) -0.1118(5) 0.0923(4) 0.045(2) Uani 1 1 d . . . . .
C33 C 0.2280(9) -0.1692(6) 0.1264(4) 0.057(2) Uani 1 1 d . . . . .
H33 H 0.2934 -0.1480 0.1562 0.068 Uiso 1 1 calc R U . . .
C34 C 0.2166(10) -0.2570(7) 0.1169(6) 0.075(3) Uani 1 1 d . . . . .
H34 H 0.2723 -0.2949 0.1410 0.090 Uiso 1 1 calc R U . . .
C35 C 0.1232(13) -0.2886(7) 0.0720(6) 0.088(4) Uani 1 1 d . . . . .
H35 H 0.1162 -0.3482 0.0652 0.105 Uiso 1 1 calc R U . . .
C36 C 0.0407(11) -0.2340(6) 0.0373(5) 0.082(3) Uani 1 1 d . . . . .
H36 H -0.0221 -0.2561 0.0066 0.098 Uiso 1 1 calc R U . . .
C37 C 0.0492(9) -0.1450(6) 0.0473(4) 0.061(2) Uani 1 1 d . . . . .
H37 H -0.0087 -0.1078 0.0238 0.073 Uiso 1 1 calc R U . . .
C38 C 0.0326(8) 0.2231(5) 0.2644(4) 0.048(2) Uani 1 1 d . . . . .
H38A H -0.0590 0.2262 0.2490 0.072 Uiso 1 1 calc R U . . .
H38B H 0.0450 0.2439 0.3074 0.072 Uiso 1 1 calc R U . . .
H38C H 0.0619 0.1640 0.2631 0.072 Uiso 1 1 calc R U . . .
C39 C 0.0638(8) 0.4292(5) 0.2730(4) 0.056(2) Uani 1 1 d . . . . .
H39A H -0.0250 0.4425 0.2565 0.084 Uiso 1 1 calc R U . . .
H39B H 0.1139 0.4819 0.2781 0.084 Uiso 1 1 calc R U . . .
H39C H 0.0637 0.4010 0.3135 0.084 Uiso 1 1 calc R U . . .
C40 C 0.2283(9) 0.4903(5) 0.1620(5) 0.064(3) Uani 1 1 d . . . . .
H40A H 0.3091 0.5040 0.1873 0.096 Uiso 1 1 calc R U . . .
H40B H 0.1601 0.5284 0.1732 0.096 Uiso 1 1 calc R U . . .
H40C H 0.2398 0.4975 0.1179 0.096 Uiso 1 1 calc R U . . .
C41 C 0.2922(9) 0.3238(6) 0.0814(4) 0.067(3) Uani 1 1 d . . . . .
H41A H 0.2301 0.3360 0.0453 0.101 Uiso 1 1 calc R U . . .
H41B H 0.3307 0.2677 0.0764 0.101 Uiso 1 1 calc R U . . .
H41C H 0.3600 0.3672 0.0847 0.101 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C1 2.002(7) . ?
Ir1 O1 2.104(5) . ?
Ir1 C23 2.132(7) . ?
Ir1 C22 2.138(7) . ?
Ir1 C21 2.163(7) . ?
Ir1 C25 2.210(8) . ?
Ir1 C24 2.220(7) . ?
Ir1 Cl1 2.4079(18) . ?
N1 C1 1.366(8) . ?
N1 C3 1.402(9) . ?
N1 C8 1.438(8) . ?
N2 C1 1.362(8) . ?
N2 C2 1.401(9) . ?
N2 C14 1.442(9) . ?
O1 C9 1.328(8) . ?
C2 C7 1.380(10) . ?
C2 C3 1.391(10) . ?
C3 C4 1.360(10) . ?
C4 C5 1.374(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(11) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.384(10) . ?
C8 C9 1.392(10) . ?
C9 C10 1.403(9) . ?
C10 C11 1.360(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.512(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.380(10) . ?
C15 C20 1.384(9) . ?
C16 C17 1.388(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.339(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(11) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.425(10) . ?
C21 C25 1.452(10) . ?
C21 C26 1.508(10) . ?
C22 C23 1.429(10) . ?
C22 C38 1.491(9) . ?
C23 C24 1.443(10) . ?
C23 C39 1.506(10) . ?
C24 C25 1.389(10) . ?
C24 C40 1.508(10) . ?
C25 C41 1.500(11) . ?
C26 C31 1.391(9) . ?
C26 C27 1.391(10) . ?
C27 C28 1.367(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.385(10) . ?
C28 H28 0.9300 . ?
C29 C30 1.387(10) . ?
C29 C32 1.496(10) . ?
C30 C31 1.380(10) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.382(11) . ?
C32 C37 1.385(11) . ?
C33 C34 1.370(12) . ?
C33 H33 0.9300 . ?
C34 C35 1.364(15) . ?
C34 H34 0.9300 . ?
C35 C36 1.352(15) . ?
C35 H35 0.9300 . ?
C36 C37 1.388(13) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ir1 O1 83.5(2) . . ?
C1 Ir1 C23 114.7(3) . . ?
O1 Ir1 C23 100.8(2) . . ?
C1 Ir1 C22 101.3(3) . . ?
O1 Ir1 C22 138.0(2) . . ?
C23 Ir1 C22 39.1(3) . . ?
C1 Ir1 C21 121.4(3) . . ?
O1 Ir1 C21 154.4(2) . . ?
C23 Ir1 C21 65.0(3) . . ?
C22 Ir1 C21 38.7(3) . . ?
C1 Ir1 C25 160.0(3) . . ?
O1 Ir1 C25 116.5(2) . . ?
C23 Ir1 C25 63.9(3) . . ?
C22 Ir1 C25 64.4(3) . . ?
C21 Ir1 C25 38.8(3) . . ?
C1 Ir1 C24 151.7(3) . . ?
O1 Ir1 C24 92.0(2) . . ?
C23 Ir1 C24 38.7(3) . . ?
C22 Ir1 C24 64.2(3) . . ?
C21 Ir1 C24 63.4(3) . . ?
C25 Ir1 C24 36.5(3) . . ?
C1 Ir1 Cl1 84.45(19) . . ?
O1 Ir1 Cl1 83.34(14) . . ?
C23 Ir1 Cl1 160.6(2) . . ?
C22 Ir1 Cl1 138.4(2) . . ?
C21 Ir1 Cl1 103.49(18) . . ?
C25 Ir1 Cl1 97.15(19) . . ?
C24 Ir1 Cl1 122.9(2) . . ?
C1 N1 C3 111.3(6) . . ?
C1 N1 C8 123.8(6) . . ?
C3 N1 C8 125.0(6) . . ?
C1 N2 C2 110.7(6) . . ?
C1 N2 C14 126.8(7) . . ?
C2 N2 C14 122.5(6) . . ?
C9 O1 Ir1 115.5(4) . . ?
N2 C1 N1 105.5(6) . . ?
N2 C1 Ir1 130.2(5) . . ?
N1 C1 Ir1 123.3(5) . . ?
C7 C2 C3 122.2(7) . . ?
C7 C2 N2 131.0(7) . . ?
C3 C2 N2 106.7(6) . . ?
C4 C3 C2 121.0(7) . . ?
C4 C3 N1 133.3(7) . . ?
C2 C3 N1 105.6(6) . . ?
C3 C4 C5 117.4(8) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C6 121.4(8) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.6(8) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 116.3(7) . . ?
C6 C7 H7 121.9 . . ?
C2 C7 H7 121.9 . . ?
C13 C8 C9 121.4(7) . . ?
C13 C8 N1 120.4(7) . . ?
C9 C8 N1 118.2(6) . . ?
O1 C9 C8 121.4(6) . . ?
O1 C9 C10 121.0(7) . . ?
C8 C9 C10 117.5(7) . . ?
C11 C10 C9 120.5(8) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 122.0(7) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C12 C13 118.8(7) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C8 C13 C12 119.7(7) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N2 C14 C15 113.6(6) . . ?
N2 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N2 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C20 119.2(7) . . ?
C16 C15 C14 122.5(7) . . ?
C20 C15 C14 118.3(7) . . ?
C15 C16 C17 119.8(8) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 119.7(8) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 119.9(8) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 121.5(8) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 119.8(8) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C22 C21 C25 107.4(6) . . ?
C22 C21 C26 126.1(6) . . ?
C25 C21 C26 125.8(6) . . ?
C22 C21 Ir1 69.7(4) . . ?
C25 C21 Ir1 72.4(4) . . ?
C26 C21 Ir1 130.8(5) . . ?
C21 C22 C23 108.0(6) . . ?
C21 C22 C38 126.0(7) . . ?
C23 C22 C38 125.8(7) . . ?
C21 C22 Ir1 71.6(4) . . ?
C23 C22 Ir1 70.2(4) . . ?
C38 C22 Ir1 127.7(5) . . ?
C22 C23 C24 107.5(6) . . ?
C22 C23 C39 126.4(7) . . ?
C24 C23 C39 125.5(7) . . ?
C22 C23 Ir1 70.7(4) . . ?
C24 C23 Ir1 74.0(4) . . ?
C39 C23 Ir1 127.9(5) . . ?
C25 C24 C23 108.6(6) . . ?
C25 C24 C40 127.0(7) . . ?
C23 C24 C40 124.1(7) . . ?
C25 C24 Ir1 71.3(4) . . ?
C23 C24 Ir1 67.4(4) . . ?
C40 C24 Ir1 122.5(5) . . ?
C24 C25 C21 108.4(6) . . ?
C24 C25 C41 126.2(7) . . ?
C21 C25 C41 125.3(7) . . ?
C24 C25 Ir1 72.1(4) . . ?
C21 C25 Ir1 68.9(4) . . ?
C41 C25 Ir1 127.0(6) . . ?
C31 C26 C27 118.3(7) . . ?
C31 C26 C21 118.8(7) . . ?
C27 C26 C21 122.8(6) . . ?
C28 C27 C26 121.1(7) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C27 C28 C29 121.1(7) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C28 C29 C30 117.5(7) . . ?
C28 C29 C32 121.5(7) . . ?
C30 C29 C32 120.9(7) . . ?
C31 C30 C29 122.0(7) . . ?
C31 C30 H30 119.0 . . ?
C29 C30 H30 119.0 . . ?
C30 C31 C26 119.6(7) . . ?
C30 C31 H31 120.2 . . ?
C26 C31 H31 120.2 . . ?
C33 C32 C37 118.3(8) . . ?
C33 C32 C29 120.7(8) . . ?
C37 C32 C29 121.0(8) . . ?
C34 C33 C32 121.1(9) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C35 C34 C33 119.8(10) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C36 C35 C34 120.4(10) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 120.4(10) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C32 C37 C36 119.8(9) . . ?
C32 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C22 C38 H38A 109.5 . . ?
C22 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C22 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C23 C39 H39A 109.5 . . ?
C23 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C23 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C24 C40 H40A 109.5 . . ?
C24 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C24 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C25 C41 H41A 109.5 . . ?
C25 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C25 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 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
C2 N2 C1 N1 -5.3(7) . . . . ?
C14 N2 C1 N1 177.4(7) . . . . ?
C2 N2 C1 Ir1 163.6(5) . . . . ?
C14 N2 C1 Ir1 -13.7(11) . . . . ?
C3 N1 C1 N2 5.2(7) . . . . ?
C8 N1 C1 N2 -175.3(6) . . . . ?
C3 N1 C1 Ir1 -164.7(5) . . . . ?
C8 N1 C1 Ir1 14.8(9) . . . . ?
C1 N2 C2 C7 -173.8(7) . . . . ?
C14 N2 C2 C7 3.6(12) . . . . ?
C1 N2 C2 C3 3.6(8) . . . . ?
C14 N2 C2 C3 -179.0(6) . . . . ?
C7 C2 C3 C4 1.8(11) . . . . ?
N2 C2 C3 C4 -175.9(7) . . . . ?
C7 C2 C3 N1 177.3(6) . . . . ?
N2 C2 C3 N1 -0.3(7) . . . . ?
C1 N1 C3 C4 171.7(8) . . . . ?
C8 N1 C3 C4 -7.8(12) . . . . ?
C1 N1 C3 C2 -3.0(7) . . . . ?
C8 N1 C3 C2 177.4(6) . . . . ?
C2 C3 C4 C5 0.0(11) . . . . ?
N1 C3 C4 C5 -174.1(7) . . . . ?
C3 C4 C5 C6 -0.9(12) . . . . ?
C4 C5 C6 C7 0.2(13) . . . . ?
C5 C6 C7 C2 1.4(12) . . . . ?
C3 C2 C7 C6 -2.4(11) . . . . ?
N2 C2 C7 C6 174.6(7) . . . . ?
C1 N1 C8 C13 140.2(7) . . . . ?
C3 N1 C8 C13 -40.3(10) . . . . ?
C1 N1 C8 C9 -38.9(9) . . . . ?
C3 N1 C8 C9 140.6(7) . . . . ?
Ir1 O1 C9 C8 52.4(8) . . . . ?
Ir1 O1 C9 C10 -128.1(6) . . . . ?
C13 C8 C9 O1 -178.9(6) . . . . ?
N1 C8 C9 O1 0.3(10) . . . . ?
C13 C8 C9 C10 1.7(10) . . . . ?
N1 C8 C9 C10 -179.2(6) . . . . ?
O1 C9 C10 C11 -179.5(6) . . . . ?
C8 C9 C10 C11 0.0(10) . . . . ?
C9 C10 C11 C12 -2.1(12) . . . . ?
C10 C11 C12 C13 2.5(12) . . . . ?
C9 C8 C13 C12 -1.3(11) . . . . ?
N1 C8 C13 C12 179.6(6) . . . . ?
C11 C12 C13 C8 -0.8(11) . . . . ?
C1 N2 C14 C15 -122.9(8) . . . . ?
C2 N2 C14 C15 60.1(9) . . . . ?
N2 C14 C15 C16 26.4(11) . . . . ?
N2 C14 C15 C20 -152.4(7) . . . . ?
C20 C15 C16 C17 0.4(12) . . . . ?
C14 C15 C16 C17 -178.5(7) . . . . ?
C15 C16 C17 C18 -1.2(13) . . . . ?
C16 C17 C18 C19 1.3(13) . . . . ?
C17 C18 C19 C20 -0.6(14) . . . . ?
C18 C19 C20 C15 -0.3(13) . . . . ?
C16 C15 C20 C19 0.4(11) . . . . ?
C14 C15 C20 C19 179.2(7) . . . . ?
C25 C21 C22 C23 -1.8(8) . . . . ?
C26 C21 C22 C23 -172.5(6) . . . . ?
Ir1 C21 C22 C23 61.2(5) . . . . ?
C25 C21 C22 C38 173.3(7) . . . . ?
C26 C21 C22 C38 2.6(12) . . . . ?
Ir1 C21 C22 C38 -123.8(8) . . . . ?
C25 C21 C22 Ir1 -63.0(5) . . . . ?
C26 C21 C22 Ir1 126.4(7) . . . . ?
C21 C22 C23 C24 3.3(8) . . . . ?
C38 C22 C23 C24 -171.8(7) . . . . ?
Ir1 C22 C23 C24 65.3(5) . . . . ?
C21 C22 C23 C39 174.5(7) . . . . ?
C38 C22 C23 C39 -0.5(12) . . . . ?
Ir1 C22 C23 C39 -123.4(8) . . . . ?
C21 C22 C23 Ir1 -62.1(5) . . . . ?
C38 C22 C23 Ir1 122.9(8) . . . . ?
C22 C23 C24 C25 -3.5(8) . . . . ?
C39 C23 C24 C25 -174.9(7) . . . . ?
Ir1 C23 C24 C25 59.6(5) . . . . ?
C22 C23 C24 C40 -178.0(7) . . . . ?
C39 C23 C24 C40 10.6(12) . . . . ?
Ir1 C23 C24 C40 -114.9(7) . . . . ?
C22 C23 C24 Ir1 -63.1(5) . . . . ?
C39 C23 C24 Ir1 125.5(8) . . . . ?
C23 C24 C25 C21 2.4(9) . . . . ?
C40 C24 C25 C21 176.7(7) . . . . ?
Ir1 C24 C25 C21 59.6(5) . . . . ?
C23 C24 C25 C41 179.7(8) . . . . ?
C40 C24 C25 C41 -6.0(13) . . . . ?
Ir1 C24 C25 C41 -123.2(9) . . . . ?
C23 C24 C25 Ir1 -57.2(5) . . . . ?
C40 C24 C25 Ir1 117.1(8) . . . . ?
C22 C21 C25 C24 -0.4(9) . . . . ?
C26 C21 C25 C24 170.3(7) . . . . ?
Ir1 C21 C25 C24 -61.6(5) . . . . ?
C22 C21 C25 C41 -177.7(8) . . . . ?
C26 C21 C25 C41 -7.0(12) . . . . ?
Ir1 C21 C25 C41 121.1(8) . . . . ?
C22 C21 C25 Ir1 61.2(5) . . . . ?
C26 C21 C25 Ir1 -128.1(7) . . . . ?
C22 C21 C26 C31 53.8(10) . . . . ?
C25 C21 C26 C31 -115.2(8) . . . . ?
Ir1 C21 C26 C31 147.3(6) . . . . ?
C22 C21 C26 C27 -124.8(8) . . . . ?
C25 C21 C26 C27 66.2(10) . . . . ?
Ir1 C21 C26 C27 -31.3(11) . . . . ?
C31 C26 C27 C28 -5.4(12) . . . . ?
C21 C26 C27 C28 173.2(7) . . . . ?
C26 C27 C28 C29 2.3(13) . . . . ?
C27 C28 C29 C30 2.9(12) . . . . ?
C27 C28 C29 C32 -173.3(8) . . . . ?
C28 C29 C30 C31 -5.1(12) . . . . ?
C32 C29 C30 C31 171.2(7) . . . . ?
C29 C30 C31 C26 2.0(12) . . . . ?
C27 C26 C31 C30 3.2(11) . . . . ?
C21 C26 C31 C30 -175.4(7) . . . . ?
C28 C29 C32 C33 38.8(11) . . . . ?
C30 C29 C32 C33 -137.3(8) . . . . ?
C28 C29 C32 C37 -143.0(9) . . . . ?
C30 C29 C32 C37 41.0(11) . . . . ?
C37 C32 C33 C34 -1.2(13) . . . . ?
C29 C32 C33 C34 177.1(7) . . . . ?
C32 C33 C34 C35 1.7(14) . . . . ?
C33 C34 C35 C36 -0.8(17) . . . . ?
C34 C35 C36 C37 -0.6(17) . . . . ?
C33 C32 C37 C36 -0.2(13) . . . . ?
C29 C32 C37 C36 -178.5(8) . . . . ?
C35 C36 C37 C32 1.1(15) . . . . ?

_refine_diff_density_max         2.276
_refine_diff_density_min         -2.291
_refine_diff_density_rms         0.155

