# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Ir-NO
_database_code_depnum_ccdc_archive 'CCDC 1864843'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.	2019-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C45 H29 Ir N4 O2), H4 O2'
_chemical_formula_sum            'C180 H120 Ir4 N16 O10'
_chemical_formula_weight         3435.71

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   37.650(3)
_cell_length_b                   9.272(2)
_cell_length_c                   20.135(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.852(2)
_cell_angle_gamma                90
_cell_volume                     6979(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4311
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      25.52

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             3400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    3.874
_shelx_estimated_absorpt_T_min   0.432
_shelx_estimated_absorpt_T_max   0.483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_T_max  0.48
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24457
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.089
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             5890
_reflns_number_gt                4553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 2008)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_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)+(0.05P)²+1.55P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5890
_refine_ls_number_parameters     475
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
C1 C 0.06434(17) 0.1736(7) -0.0045(3) 0.0408(16) Uani 1 1 d . . . . .
H1 H 0.043312 0.184158 0.014977 0.049 Uiso 1 1 calc R U . . .
C2 C 0.06374(18) 0.0981(7) -0.0635(3) 0.0430(17) Uani 1 1 d . . . . .
H2 H 0.042453 0.057816 -0.083384 0.052 Uiso 1 1 calc R U . . .
C3 C 0.09477(18) 0.0820(8) -0.0933(3) 0.0456(17) Uani 1 1 d . . . . .
H3 H 0.094854 0.029829 -0.132676 0.055 Uiso 1 1 calc R U . . .
C4 C 0.12527(19) 0.1450(7) -0.0631(3) 0.0440(17) Uani 1 1 d . . . . .
H4 H 0.146345 0.136656 -0.082594 0.053 Uiso 1 1 calc R U . . .
C5 C 0.12538(16) 0.2219(6) -0.0033(3) 0.0314(14) Uani 1 1 d . . . . .
C6 C 0.15542(16) 0.2983(6) 0.0318(3) 0.0307(14) Uani 1 1 d . . . . .
C7 C 0.18836(18) 0.3144(7) 0.0058(3) 0.0430(17) Uani 1 1 d . . . . .
H7 H 0.191976 0.267912 -0.033713 0.052 Uiso 1 1 calc R U . . .
C8 C 0.21475(16) 0.3967(7) 0.0377(3) 0.0371(15) Uani 1 1 d . . . . .
C9 C 0.20903(15) 0.4725(7) 0.0947(3) 0.0385(16) Uani 1 1 d . . . . .
C10 C 0.17729(16) 0.4551(7) 0.1233(3) 0.0378(15) Uani 1 1 d . . . . .
C11 C 0.14948(16) 0.3668(6) 0.0930(3) 0.0312(14) Uani 1 1 d . . . . .
C12 C 0.26717(17) 0.5275(8) 0.0282(3) 0.0457(17) Uani 1 1 d . . . . .
C13 C 0.29201(19) 0.5705(10) -0.0131(4) 0.065(2) Uani 1 1 d . . . . .
H13 H 0.295838 0.513425 -0.049565 0.077 Uiso 1 1 calc R U . . .
C14 C 0.3107(2) 0.6931(9) -0.0017(5) 0.062(2) Uani 1 1 d . . . . .
H14 H 0.327139 0.720475 -0.030322 0.075 Uiso 1 1 calc R U . . .
C15 C 0.30545(19) 0.7800(9) 0.0534(5) 0.065(2) Uani 1 1 d . . . . .
H15 H 0.318679 0.864296 0.061008 0.078 Uiso 1 1 calc R U . . .
C16 C 0.2806(2) 0.7421(9) 0.0973(4) 0.063(2) Uani 1 1 d . . . . .
H16 H 0.276757 0.801512 0.133010 0.076 Uiso 1 1 calc R U . . .
C17 C 0.26141(18) 0.6097(8) 0.0856(4) 0.0486(18) Uani 1 1 d . . . . .
C18 C 0.23550(17) 0.5910(8) 0.1944(3) 0.0454(17) Uani 1 1 d . . . . .
C19 C 0.26526(18) 0.6306(8) 0.2376(4) 0.053(2) Uani 1 1 d . . . . .
H19 H 0.286988 0.645305 0.221026 0.064 Uiso 1 1 calc R U . . .
C20 C 0.2631(2) 0.6482(9) 0.3043(4) 0.066(2) Uani 1 1 d . . . . .
H20 H 0.283332 0.675610 0.332604 0.079 Uiso 1 1 calc R U . . .
C21 C 0.2306(2) 0.6254(10) 0.3308(4) 0.069(2) Uani 1 1 d . . . . .
H21 H 0.229086 0.639739 0.376041 0.083 Uiso 1 1 calc R U . . .
C22 C 0.20058(19) 0.5805(8) 0.2876(4) 0.0539(19) Uani 1 1 d . . . . .
H22 H 0.179146 0.560584 0.304421 0.065 Uiso 1 1 calc R U . . .
C23 C 0.20311(17) 0.5661(7) 0.2198(3) 0.0413(16) Uani 1 1 d . . . . .
C24 C 0.1259(2) 0.0190(8) 0.1457(3) 0.0534(18) Uani 1 1 d . U . . .
H24 H 0.120059 0.006633 0.099904 0.064 Uiso 1 1 calc R U . . .
C25 C 0.1414(2) -0.0958(9) 0.1838(4) 0.067(2) Uani 1 1 d . . . . .
H25 H 0.145869 -0.182793 0.163377 0.080 Uiso 1 1 calc R U . . .
C26 C 0.1500(2) -0.0791(9) 0.2511(4) 0.061(2) Uani 1 1 d . . . . .
H26 H 0.160053 -0.154517 0.277334 0.073 Uiso 1 1 calc R U . . .
C27 C 0.14347(18) 0.0484(8) 0.2784(4) 0.0500(19) Uani 1 1 d . . . . .
H27 H 0.149467 0.062302 0.324063 0.060 Uiso 1 1 calc R U . . .
C28 C 0.12761(16) 0.1621(7) 0.2385(3) 0.0373(15) Uani 1 1 d . . . . .
C29 C 0.11901(16) 0.3052(7) 0.2648(3) 0.0415(17) Uani 1 1 d . . . . .
C30 C 0.12137(19) 0.3394(9) 0.3324(3) 0.055(2) Uani 1 1 d . . . . .
H30 H 0.128764 0.269441 0.364141 0.066 Uiso 1 1 calc R U . . .
C31 C 0.11313(19) 0.4722(9) 0.3526(3) 0.057(2) Uani 1 1 d . . . . .
H31 H 0.115653 0.494137 0.397961 0.069 Uiso 1 1 calc R U . . .
C32 C 0.1008(2) 0.5774(9) 0.3059(4) 0.056(2) Uani 1 1 d . . . . .
H32 H 0.094554 0.668447 0.319952 0.068 Uiso 1 1 calc R U . . .
C33 C 0.09801(17) 0.5448(7) 0.2387(3) 0.0436(17) Uani 1 1 d . . . . .
H33 H 0.090256 0.616919 0.208246 0.052 Uiso 1 1 calc R U . . .
C34 C 0.10610(16) 0.4107(7) 0.2138(3) 0.0328(14) Uani 1 1 d . . . . .
C35 C 0.0312(2) 0.1892(8) 0.1591(3) 0.0506(19) Uani 1 1 d . . . . .
H35 H 0.045769 0.110008 0.171023 0.061 Uiso 1 1 calc R U . . .
C36 C -0.0049(2) 0.1851(10) 0.1682(4) 0.061(2) Uani 1 1 d . . . . .
H36 H -0.014251 0.103845 0.186945 0.074 Uiso 1 1 calc R U . . .
C37 C -0.0265(2) 0.2994(11) 0.1500(4) 0.074(3) Uani 1 1 d . . . . .
H37 H -0.050546 0.297535 0.156300 0.089 Uiso 1 1 calc R U . . .
C38 C -0.0124(2) 0.4156(10) 0.1225(4) 0.065(2) Uani 1 1 d . . . . .
H38 H -0.027054 0.493549 0.109200 0.078 Uiso 1 1 calc R U . . .
C39 C 0.02315(18) 0.4212(8) 0.1139(3) 0.0436(17) Uani 1 1 d . . . . .
C40 C 0.04180(18) 0.5384(7) 0.0847(3) 0.0448(17) Uani 1 1 d . . . . .
C41 C 0.0245(2) 0.6624(9) 0.0595(4) 0.066(2) Uani 1 1 d . . . . .
H41 H 0.000305 0.674037 0.063108 0.080 Uiso 1 1 calc R U . . .
C42 C 0.0424(2) 0.7677(10) 0.0297(4) 0.071(2) Uani 1 1 d . . . . .
H42 H 0.030262 0.850427 0.013626 0.085 Uiso 1 1 calc R U . . .
C43 C 0.0784(2) 0.7521(9) 0.0231(4) 0.065(2) Uani 1 1 d . . . . .
H43 H 0.090548 0.823358 0.002415 0.078 Uiso 1 1 calc R U . . .
C44 C 0.0960(2) 0.6289(7) 0.0479(3) 0.0508(19) Uani 1 1 d . . . . .
H44 H 0.120151 0.618838 0.043278 0.061 Uiso 1 1 calc R U . . .
C45 C 0.07870(15) 0.5175(7) 0.0799(3) 0.0338(14) Uani 1 1 d . . . . .
Ir1 Ir 0.09956(2) 0.33393(3) 0.11985(2) 0.02980(10) Uani 1 1 d . . . . .
N1 N 0.09445(13) 0.2317(5) 0.0251(2) 0.0279(11) Uani 1 1 d . . . . .
N2 N 0.23581(15) 0.5660(6) 0.1246(3) 0.0508(15) Uani 1 1 d . . . . .
N3 N 0.11928(14) 0.1441(5) 0.1727(2) 0.0369(12) Uani 1 1 d . U . . .
N4 N 0.04509(13) 0.3065(6) 0.1331(2) 0.0374(13) Uani 1 1 d . . . . .
O1 O 0.24711(12) 0.4067(6) 0.0122(2) 0.0550(13) Uani 1 1 d . . . . .
O2 O 0.17246(11) 0.5337(5) 0.1798(2) 0.0465(12) Uani 1 1 d . . . . .
O1W O 0.0437(4) 0.8586(17) 0.2370(7) 0.034 Uani 0.25 1 d . . P A 1
H1X H 0.045688 0.786104 0.211851 0.041 Uiso 0.25 1 d R U P A 1
H1Y H 0.022518 0.891134 0.230391 0.041 Uiso 0.25 1 d R U P A 1
O2W O 0.0223(4) 0.7888(16) 0.2305(7) 0.028 Uani 0.25 1 d . . P B 2
H2X H 0.031896 0.776913 0.270511 0.034 Uiso 0.25 1 d R U P B 2
H2Y H 0.029656 0.867273 0.215201 0.034 Uiso 0.25 1 d R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.330(7) . ?
C1 C2 1.377(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(8) . ?
C4 H4 0.9300 . ?
C5 N1 1.360(7) . ?
C5 C6 1.445(8) . ?
C6 C7 1.410(9) . ?
C6 C11 1.428(8) . ?
C7 C8 1.352(9) . ?
C7 H7 0.9300 . ?
C8 O1 1.381(7) . ?
C8 C9 1.385(8) . ?
C9 C10 1.396(8) . ?
C9 N2 1.409(8) . ?
C10 O2 1.382(7) . ?
C10 C11 1.409(8) . ?
C11 Ir1 2.039(6) . ?
C12 O1 1.368(8) . ?
C12 C13 1.383(9) . ?
C12 C17 1.421(10) . ?
C13 C14 1.342(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.404(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.407(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.430(10) . ?
C16 H16 0.9300 . ?
C17 N2 1.376(8) . ?
C18 C19 1.384(9) . ?
C18 C23 1.397(9) . ?
C18 N2 1.424(8) . ?
C19 C20 1.365(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.406(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.405(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(9) . ?
C22 H22 0.9300 . ?
C23 O2 1.360(7) . ?
C24 N3 1.317(8) . ?
C24 C25 1.398(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.363(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.339(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.413(9) . ?
C27 H27 0.9300 . ?
C28 N3 1.335(8) . ?
C28 C29 1.479(9) . ?
C29 C30 1.390(9) . ?
C29 C34 1.459(9) . ?
C30 C31 1.344(10) . ?
C30 H30 0.9300 . ?
C31 C32 1.395(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.378(9) . ?
C32 H32 0.9300 . ?
C33 C34 1.388(8) . ?
C33 H33 0.9300 . ?
C34 Ir1 2.008(6) . ?
C35 N4 1.340(8) . ?
C35 C36 1.395(10) . ?
C35 H35 0.9300 . ?
C36 C37 1.360(11) . ?
C36 H36 0.9300 . ?
C37 C38 1.348(11) . ?
C37 H37 0.9300 . ?
C38 C39 1.370(10) . ?
C38 H38 0.9300 . ?
C39 N4 1.373(8) . ?
C39 C40 1.455(9) . ?
C40 C41 1.386(9) . ?
C40 C45 1.417(9) . ?
C41 C42 1.364(11) . ?
C41 H41 0.9300 . ?
C42 C43 1.386(11) . ?
C42 H42 0.9300 . ?
C43 C44 1.383(10) . ?
C43 H43 0.9300 . ?
C44 C45 1.418(9) . ?
C44 H44 0.9300 . ?
C45 Ir1 2.002(6) . ?
Ir1 N4 2.115(5) . ?
Ir1 N1 2.119(5) . ?
Ir1 N3 2.143(5) . ?
O1W H1X 0.8500 . ?
O1W H1Y 0.8500 . ?
O2W H2X 0.8500 . ?
O2W H2Y 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.2(6) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 120.0(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 118.1(6) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.2(6) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N1 C5 C4 118.7(6) . . ?
N1 C5 C6 114.9(5) . . ?
C4 C5 C6 126.3(6) . . ?
C7 C6 C11 120.5(5) . . ?
C7 C6 C5 122.9(5) . . ?
C11 C6 C5 116.4(5) . . ?
C8 C7 C6 120.9(6) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 O1 119.5(6) . . ?
C7 C8 C9 120.1(6) . . ?
O1 C8 C9 120.4(6) . . ?
C8 C9 C10 120.5(6) . . ?
C8 C9 N2 119.6(5) . . ?
C10 C9 N2 119.9(6) . . ?
O2 C10 C9 118.8(5) . . ?
O2 C10 C11 119.9(5) . . ?
C9 C10 C11 121.2(6) . . ?
C10 C11 C6 116.5(5) . . ?
C10 C11 Ir1 129.3(5) . . ?
C6 C11 Ir1 114.0(4) . . ?
O1 C12 C13 119.2(7) . . ?
O1 C12 C17 119.8(6) . . ?
C13 C12 C17 120.9(7) . . ?
C14 C13 C12 121.3(8) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 120.1(8) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 121.4(8) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 118.1(8) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
N2 C17 C12 119.5(6) . . ?
N2 C17 C16 122.2(7) . . ?
C12 C17 C16 118.2(6) . . ?
C19 C18 C23 119.3(6) . . ?
C19 C18 N2 124.2(6) . . ?
C23 C18 N2 116.4(6) . . ?
C20 C19 C18 120.8(7) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 120.7(7) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 118.9(7) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C23 C22 C21 119.5(7) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
O2 C23 C22 116.8(6) . . ?
O2 C23 C18 122.3(6) . . ?
C22 C23 C18 120.7(6) . . ?
N3 C24 C25 122.1(6) . . ?
N3 C24 H24 118.9 . . ?
C25 C24 H24 118.9 . . ?
C26 C25 C24 119.5(7) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C27 C26 C25 118.4(7) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
C26 C27 C28 120.7(7) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
N3 C28 C27 120.2(6) . . ?
N3 C28 C29 115.6(5) . . ?
C27 C28 C29 124.2(6) . . ?
C30 C29 C34 120.9(7) . . ?
C30 C29 C28 124.3(6) . . ?
C34 C29 C28 114.7(5) . . ?
C31 C30 C29 121.0(7) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 120.4(7) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C33 C32 C31 119.3(7) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C32 C33 C34 123.8(7) . . ?
C32 C33 H33 118.1 . . ?
C34 C33 H33 118.1 . . ?
C33 C34 C29 114.5(6) . . ?
C33 C34 Ir1 130.6(5) . . ?
C29 C34 Ir1 114.7(4) . . ?
N4 C35 C36 120.3(7) . . ?
N4 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 120.3(7) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C38 C37 C36 118.8(8) . . ?
C38 C37 H37 120.6 . . ?
C36 C37 H37 120.6 . . ?
C37 C38 C39 121.4(8) . . ?
C37 C38 H38 119.3 . . ?
C39 C38 H38 119.3 . . ?
C38 C39 N4 119.9(7) . . ?
C38 C39 C40 127.2(7) . . ?
N4 C39 C40 112.9(6) . . ?
C41 C40 C45 120.6(7) . . ?
C41 C40 C39 122.6(7) . . ?
C45 C40 C39 116.7(6) . . ?
C42 C41 C40 121.4(7) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
C41 C42 C43 120.4(8) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C44 C43 C42 118.9(8) . . ?
C44 C43 H43 120.5 . . ?
C42 C43 H43 120.5 . . ?
C43 C44 C45 122.7(7) . . ?
C43 C44 H44 118.7 . . ?
C45 C44 H44 118.7 . . ?
C40 C45 C44 116.0(6) . . ?
C40 C45 Ir1 115.5(5) . . ?
C44 C45 Ir1 128.5(5) . . ?
C45 Ir1 C34 94.3(2) . . ?
C45 Ir1 C11 95.5(2) . . ?
C34 Ir1 C11 100.6(2) . . ?
C45 Ir1 N4 79.2(2) . . ?
C34 Ir1 N4 86.3(2) . . ?
C11 Ir1 N4 171.7(2) . . ?
C45 Ir1 N1 91.7(2) . . ?
C34 Ir1 N1 174.0(2) . . ?
C11 Ir1 N1 79.4(2) . . ?
N4 Ir1 N1 94.27(18) . . ?
C45 Ir1 N3 173.5(2) . . ?
C34 Ir1 N3 80.1(2) . . ?
C11 Ir1 N3 88.8(2) . . ?
N4 Ir1 N3 97.0(2) . . ?
N1 Ir1 N3 93.92(18) . . ?
C1 N1 C5 120.7(5) . . ?
C1 N1 Ir1 124.5(4) . . ?
C5 N1 Ir1 114.7(4) . . ?
C17 N2 C9 116.8(6) . . ?
C17 N2 C18 127.2(6) . . ?
C9 N2 C18 115.6(5) . . ?
C24 N3 C28 119.1(6) . . ?
C24 N3 Ir1 126.2(4) . . ?
C28 N3 Ir1 114.6(4) . . ?
C35 N4 C39 119.3(6) . . ?
C35 N4 Ir1 125.1(5) . . ?
C39 N4 Ir1 115.5(4) . . ?
C12 O1 C8 117.0(5) . . ?
C23 O2 C10 114.8(5) . . ?
H1X O1W H1Y 109.5 . . ?
H2X O2W H2Y 109.5 . . ?

_refine_diff_density_max         1.888
_refine_diff_density_min         -1.238
_refine_diff_density_rms         0.151

####################################################################### 
# 
# 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_Ir-O
_database_code_depnum_ccdc_archive 'CCDC 1864844'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.	2019-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H32 Ir N3 O2'
_chemical_formula_weight         838.94

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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I-4

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   27.492(3)
_cell_length_b                   27.492(3)
_cell_length_c                   9.296(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7026(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6254
_cell_measurement_theta_min      2.313
_cell_measurement_theta_max      19.409

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3328
_exptl_absorpt_coefficient_mu    3.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4124
_exptl_absorpt_correction_T_max  0.4717
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49759
_diffrn_reflns_av_R_equivalents  0.1097
_diffrn_reflns_av_sigmaI/netI    0.0907
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.05
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6913
_reflns_number_gt                5550
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0694P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(14)
_refine_ls_number_reflns         6913
_refine_ls_number_parameters     460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.973422(14) 0.712669(15) 0.86897(4) 0.02628(13) Uani 1 1 d . . .
N1 N 0.9069(3) 0.6829(3) 0.7896(10) 0.032(2) Uani 1 1 d . . .
N2 N 0.9666(4) 0.7829(4) 0.7765(12) 0.045(3) Uani 1 1 d . . .
N3 N 1.0128(3) 0.6858(3) 0.6872(10) 0.028(2) Uani 1 1 d . . .
O1 O 0.8225(3) 0.7275(3) 1.3679(11) 0.046(2) Uani 1 1 d . . .
O2 O 0.9821(3) 0.7687(3) 1.2024(9) 0.046(2) Uani 1 1 d . . .
C1 C 0.8991(4) 0.6630(4) 0.6605(12) 0.031(3) Uani 1 1 d . . .
H1 H 0.9246 0.6630 0.5945 0.037 Uiso 1 1 calc R . .
C2 C 0.8562(4) 0.6430(4) 0.6206(16) 0.035(3) Uani 1 1 d . . .
H2 H 0.8523 0.6299 0.5291 0.042 Uiso 1 1 calc R . .
C3 C 0.8183(4) 0.6424(4) 0.7177(13) 0.036(3) Uani 1 1 d . . .
H3 H 0.7887 0.6285 0.6919 0.043 Uiso 1 1 calc R . .
C4 C 0.8240(4) 0.6618(4) 0.8507(14) 0.034(3) Uani 1 1 d . . .
H4 H 0.7986 0.6613 0.9167 0.041 Uiso 1 1 calc R . .
C5 C 0.8693(4) 0.6830(4) 0.8875(14) 0.032(3) Uani 1 1 d . . .
C6 C 0.8809(4) 0.7056(4) 1.0253(13) 0.034(3) Uani 1 1 d . . .
C7 C 0.8459(4) 0.7071(4) 1.1335(16) 0.037(3) Uani 1 1 d . . .
H7 H 0.8153 0.6935 1.1187 0.045 Uiso 1 1 calc R . .
C8 C 0.8567(5) 0.7287(5) 1.2604(14) 0.042(3) Uani 1 1 d . . .
C9 C 0.9025(5) 0.7487(5) 1.2821(14) 0.044(3) Uani 1 1 d . . .
H9 H 0.9102 0.7632 1.3695 0.052 Uiso 1 1 calc R . .
C10 C 0.9371(5) 0.7468(5) 1.1706(13) 0.041(3) Uani 1 1 d . . .
C11 C 0.9291(4) 0.7255(4) 1.0409(13) 0.034(3) Uani 1 1 d . . .
C12 C 0.9276(5) 0.7999(5) 0.6957(15) 0.047(4) Uani 1 1 d . . .
H12 H 0.8997 0.7807 0.6910 0.056 Uiso 1 1 calc R . .
C13 C 0.9278(5) 0.8427(5) 0.623(2) 0.060(4) Uani 1 1 d . . .
H13 H 0.9005 0.8528 0.5725 0.072 Uiso 1 1 calc R . .
C14 C 0.9693(5) 0.8710(5) 0.626(2) 0.065(4) Uani 1 1 d . . .
H14 H 0.9714 0.8991 0.5710 0.078 Uiso 1 1 calc R . .
C15 C 1.0083(5) 0.8567(5) 0.7131(16) 0.054(4) Uani 1 1 d . . .
H15 H 1.0357 0.8765 0.7191 0.065 Uiso 1 1 calc R . .
C16 C 1.0069(5) 0.8126(5) 0.7923(15) 0.046(3) Uani 1 1 d . . .
C17 C 1.0435(4) 0.7914(4) 0.8820(15) 0.038(3) Uani 1 1 d . . .
C18 C 1.0341(4) 0.7441(4) 0.9427(13) 0.034(3) Uani 1 1 d . . .
C19 C 1.0693(4) 0.7268(5) 1.0390(13) 0.033(3) Uani 1 1 d . . .
H19 H 1.0639 0.6971 1.0841 0.040 Uiso 1 1 calc R . .
C20 C 1.1097(4) 0.7505(5) 1.0688(13) 0.037(3) Uani 1 1 d . . .
H20 H 1.1322 0.7368 1.1316 0.045 Uiso 1 1 calc R . .
C21 C 1.1194(5) 0.7969(5) 1.0063(15) 0.043(3) Uani 1 1 d . . .
H21 H 1.1480 0.8134 1.0281 0.051 Uiso 1 1 calc R . .
C22 C 1.0864(4) 0.8166(5) 0.9145(14) 0.044(3) Uani 1 1 d . . .
H22 H 1.0923 0.8468 0.8732 0.053 Uiso 1 1 calc R . .
C23 C 1.0203(4) 0.7086(5) 0.5627(13) 0.035(3) Uani 1 1 d . . .
H23 H 1.0108 0.7410 0.5547 0.042 Uiso 1 1 calc R . .
C24 C 1.0418(4) 0.6861(5) 0.4432(12) 0.035(3) Uani 1 1 d . . .
H24 H 1.0455 0.7026 0.3565 0.043 Uiso 1 1 calc R . .
C25 C 1.0569(4) 0.6396(5) 0.4587(12) 0.035(3) Uani 1 1 d . . .
H25 H 1.0718 0.6234 0.3829 0.042 Uiso 1 1 calc R . .
C26 C 1.0500(4) 0.6174(4) 0.5858(11) 0.029(3) Uani 1 1 d . . .
H26 H 1.0607 0.5855 0.5960 0.035 Uiso 1 1 calc R . .
C27 C 1.0278(4) 0.6395(4) 0.7019(12) 0.029(3) Uani 1 1 d . . .
C28 C 1.0193(4) 0.6185(4) 0.8438(12) 0.028(3) Uani 1 1 d . . .
C29 C 1.0379(4) 0.5727(4) 0.8820(15) 0.036(3) Uani 1 1 d . . .
H29 H 1.0552 0.5548 0.8142 0.043 Uiso 1 1 calc R . .
C30 C 1.0312(4) 0.5538(5) 1.0160(13) 0.036(3) Uani 1 1 d . . .
H30 H 1.0441 0.5236 1.0401 0.043 Uiso 1 1 calc R . .
C31 C 1.0044(4) 0.5811(4) 1.1180(15) 0.038(3) Uani 1 1 d . . .
H31 H 0.9991 0.5689 1.2099 0.045 Uiso 1 1 calc R . .
C32 C 0.9860(4) 0.6263(4) 1.0798(13) 0.035(3) Uani 1 1 d . . .
H32 H 0.9682 0.6437 1.1475 0.041 Uiso 1 1 calc R . .
C33 C 0.9932(4) 0.6470(4) 0.9418(12) 0.027(3) Uani 1 1 d . . .
C34 C 0.8113(5) 0.7721(5) 1.4397(15) 0.041(3) Uani 1 1 d . . .
C35 C 0.8122(4) 0.8155(4) 1.3735(17) 0.040(3) Uani 1 1 d . . .
H35 H 0.8207 0.8168 1.2768 0.048 Uiso 1 1 calc R . .
C36 C 0.8010(5) 0.8580(5) 1.4433(14) 0.044(3) Uani 1 1 d . . .
H36 H 0.8016 0.8878 1.3960 0.053 Uiso 1 1 calc R . .
C37 C 0.7889(5) 0.8545(5) 1.5849(14) 0.046(3) Uani 1 1 d . . .
H37 H 0.7814 0.8825 1.6363 0.055 Uiso 1 1 calc R . .
C38 C 0.7877(4) 0.8094(5) 1.6544(15) 0.045(3) Uani 1 1 d . . .
H38 H 0.7802 0.8076 1.7519 0.053 Uiso 1 1 calc R . .
C39 C 0.7976(4) 0.7671(5) 1.5773(13) 0.037(3) Uani 1 1 d . . .
H39 H 0.7949 0.7366 1.6197 0.045 Uiso 1 1 calc R . .
C40 C 0.9832(6) 0.8206(6) 1.1861(19) 0.064(5) Uani 1 1 d . . .
C41 C 1.0232(6) 0.8457(7) 1.260(2) 0.081(6) Uani 1 1 d . . .
H41 H 1.0441 0.8288 1.3201 0.097 Uiso 1 1 calc R . .
C42 C 1.0287(7) 0.8912(7) 1.239(2) 0.083(6) Uani 1 1 d . . .
H42 H 1.0547 0.9073 1.2824 0.100 Uiso 1 1 calc R . .
C43 C 0.9958(7) 0.9176(7) 1.151(3) 0.096(6) Uani 1 1 d . . .
H43 H 1.0004 0.9511 1.1447 0.115 Uiso 1 1 calc R . .
C44 C 0.9585(7) 0.8985(7) 1.076(2) 0.088(6) Uani 1 1 d . . .
H44 H 0.9406 0.9169 1.0114 0.106 Uiso 1 1 calc R . .
C45 C 0.9485(6) 0.8504(6) 1.102(2) 0.068(5) Uani 1 1 d . . .
H45 H 0.9200 0.8366 1.0659 0.081 Uiso 1 1 calc 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 C18 2.000(12) . ?
Ir1 C33 2.004(11) . ?
Ir1 C11 2.040(12) . ?
Ir1 N2 2.122(11) . ?
Ir1 N1 2.136(9) . ?
Ir1 N3 2.138(9) . ?
N1 C1 1.335(14) . ?
N1 C5 1.377(14) . ?
N2 C16 1.385(17) . ?
N2 C12 1.389(16) . ?
N3 C23 1.333(14) . ?
N3 C27 1.346(14) . ?
O1 C8 1.374(15) . ?
O1 C34 1.428(14) . ?
O2 C10 1.407(14) . ?
O2 C40 1.436(18) . ?
C1 C2 1.355(15) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.460(17) . ?
C6 C7 1.393(17) . ?
C6 C11 1.440(17) . ?
C7 C8 1.353(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.388(18) . ?
C9 C10 1.407(17) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(16) . ?
C12 C13 1.36(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.40(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.418(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.431(19) . ?
C17 C22 1.400(16) . ?
C17 C18 1.442(17) . ?
C18 C19 1.401(17) . ?
C19 C20 1.318(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.425(19) . ?
C20 H20 0.9300 . ?
C21 C22 1.360(18) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.403(16) . ?
C23 H23 0.9300 . ?
C24 C25 1.351(16) . ?
C24 H24 0.9300 . ?
C25 C26 1.344(16) . ?
C25 H25 0.9300 . ?
C26 C27 1.380(15) . ?
C26 H26 0.9300 . ?
C27 C28 1.459(16) . ?
C28 C33 1.399(14) . ?
C28 C29 1.406(16) . ?
C29 C30 1.362(18) . ?
C29 H29 0.9300 . ?
C30 C31 1.418(17) . ?
C30 H30 0.9300 . ?
C31 C32 1.386(16) . ?
C31 H31 0.9300 . ?
C32 C33 1.417(16) . ?
C32 H32 0.9300 . ?
C34 C39 1.340(18) . ?
C34 C35 1.343(18) . ?
C35 C36 1.372(17) . ?
C35 H35 0.9300 . ?
C36 C37 1.361(17) . ?
C36 H36 0.9300 . ?
C37 C38 1.398(18) . ?
C37 H37 0.9300 . ?
C38 C39 1.392(17) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 C41 1.47(2) . ?
C40 C45 1.48(2) . ?
C41 C42 1.27(2) . ?
C41 H41 0.9300 . ?
C42 C43 1.42(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.35(2) . ?
C43 H43 0.9300 . ?
C44 C45 1.37(2) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?

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
C18 Ir1 C33 92.7(5) . . ?
C18 Ir1 C11 98.9(5) . . ?
C33 Ir1 C11 93.1(5) . . ?
C18 Ir1 N2 79.6(5) . . ?
C33 Ir1 N2 168.8(4) . . ?
C11 Ir1 N2 96.1(5) . . ?
C18 Ir1 N1 176.9(5) . . ?
C33 Ir1 N1 90.2(4) . . ?
C11 Ir1 N1 79.9(4) . . ?
N2 Ir1 N1 97.7(4) . . ?
C18 Ir1 N3 89.9(4) . . ?
C33 Ir1 N3 79.5(4) . . ?
C11 Ir1 N3 168.8(4) . . ?
N2 Ir1 N3 92.3(4) . . ?
N1 Ir1 N3 91.6(3) . . ?
C1 N1 C5 118.4(10) . . ?
C1 N1 Ir1 127.1(8) . . ?
C5 N1 Ir1 114.4(7) . . ?
C16 N2 C12 118.5(12) . . ?
C16 N2 Ir1 115.0(9) . . ?
C12 N2 Ir1 126.3(9) . . ?
C23 N3 C27 119.1(10) . . ?
C23 N3 Ir1 126.9(8) . . ?
C27 N3 Ir1 113.7(8) . . ?
C8 O1 C34 117.9(9) . . ?
C10 O2 C40 114.9(10) . . ?
N1 C1 C2 123.4(11) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 119.0(12) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.3(11) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 118.9(11) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 119.9(11) . . ?
N1 C5 C6 114.6(9) . . ?
C4 C5 C6 125.5(11) . . ?
C7 C6 C11 123.5(11) . . ?
C7 C6 C5 119.6(11) . . ?
C11 C6 C5 116.8(10) . . ?
C8 C7 C6 119.3(11) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 O1 118.2(11) . . ?
C7 C8 C9 120.0(12) . . ?
O1 C8 C9 121.7(11) . . ?
C8 C9 C10 119.4(12) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 124.1(12) . . ?
C11 C10 O2 120.8(11) . . ?
C9 C10 O2 115.1(10) . . ?
C10 C11 C6 113.6(11) . . ?
C10 C11 Ir1 132.3(10) . . ?
C6 C11 Ir1 113.9(8) . . ?
C13 C12 N2 123.8(14) . . ?
C13 C12 H12 118.1 . . ?
N2 C12 H12 118.1 . . ?
C12 C13 C14 118.8(14) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C15 119.1(15) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 121.3(14) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
N2 C16 C15 118.1(13) . . ?
N2 C16 C17 112.6(12) . . ?
C15 C16 C17 129.1(13) . . ?
C22 C17 C16 121.1(12) . . ?
C22 C17 C18 120.8(12) . . ?
C16 C17 C18 118.0(11) . . ?
C19 C18 C17 115.7(11) . . ?
C19 C18 Ir1 130.4(10) . . ?
C17 C18 Ir1 113.9(9) . . ?
C20 C19 C18 123.2(13) . . ?
C20 C19 H19 118.4 . . ?
C18 C19 H19 118.4 . . ?
C19 C20 C21 121.0(12) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 119.2(12) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C17 120.1(12) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
N3 C23 C24 123.0(11) . . ?
N3 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
C25 C24 C23 117.5(11) . . ?
C25 C24 H24 121.2 . . ?
C23 C24 H24 121.2 . . ?
C26 C25 C24 118.7(11) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C27 123.3(11) . . ?
C25 C26 H26 118.3 . . ?
C27 C26 H26 118.3 . . ?
N3 C27 C26 118.2(11) . . ?
N3 C27 C28 114.6(10) . . ?
C26 C27 C28 127.2(10) . . ?
C33 C28 C29 121.6(11) . . ?
C33 C28 C27 116.8(10) . . ?
C29 C28 C27 121.6(11) . . ?
C30 C29 C28 121.6(12) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C29 C30 C31 118.7(12) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C32 C31 C30 119.6(12) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C33 122.7(11) . . ?
C31 C32 H32 118.6 . . ?
C33 C32 H32 118.6 . . ?
C28 C33 C32 115.9(10) . . ?
C28 C33 Ir1 115.0(8) . . ?
C32 C33 Ir1 129.0(8) . . ?
C39 C34 C35 122.1(13) . . ?
C39 C34 O1 114.8(12) . . ?
C35 C34 O1 123.0(12) . . ?
C34 C35 C36 122.5(14) . . ?
C34 C35 H35 118.8 . . ?
C36 C35 H35 118.8 . . ?
C37 C36 C35 116.8(14) . . ?
C37 C36 H36 121.6 . . ?
C35 C36 H36 121.6 . . ?
C36 C37 C38 121.1(13) . . ?
C36 C37 H37 119.5 . . ?
C38 C37 H37 119.5 . . ?
C39 C38 C37 119.8(13) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C34 C39 C38 117.6(13) . . ?
C34 C39 H39 121.2 . . ?
C38 C39 H39 121.2 . . ?
O2 C40 C41 115.7(15) . . ?
O2 C40 C45 126.3(13) . . ?
C41 C40 C45 118.0(15) . . ?
C42 C41 C40 119(2) . . ?
C42 C41 H41 120.6 . . ?
C40 C41 H41 120.6 . . ?
C41 C42 C43 120.8(19) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 H42 119.6 . . ?
C44 C43 C42 125.7(19) . . ?
C44 C43 H43 117.1 . . ?
C42 C43 H43 117.1 . . ?
C43 C44 C45 116(2) . . ?
C43 C44 H44 121.9 . . ?
C45 C44 H44 121.9 . . ?
C44 C45 C40 119.6(16) . . ?
C44 C45 H45 120.2 . . ?
C40 C45 H45 120.2 . . ?

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
C18 Ir1 N1 C1 110(8) . . . . ?
C33 Ir1 N1 C1 -88.3(10) . . . . ?
C11 Ir1 N1 C1 178.6(10) . . . . ?
N2 Ir1 N1 C1 83.7(10) . . . . ?
N3 Ir1 N1 C1 -8.8(10) . . . . ?
C18 Ir1 N1 C5 -73(9) . . . . ?
C33 Ir1 N1 C5 88.8(8) . . . . ?
C11 Ir1 N1 C5 -4.3(8) . . . . ?
N2 Ir1 N1 C5 -99.2(8) . . . . ?
N3 Ir1 N1 C5 168.3(8) . . . . ?
C18 Ir1 N2 C16 8.0(9) . . . . ?
C33 Ir1 N2 C16 -39(3) . . . . ?
C11 Ir1 N2 C16 106.0(10) . . . . ?
N1 Ir1 N2 C16 -173.4(10) . . . . ?
N3 Ir1 N2 C16 -81.5(10) . . . . ?
C18 Ir1 N2 C12 -176.6(12) . . . . ?
C33 Ir1 N2 C12 136(2) . . . . ?
C11 Ir1 N2 C12 -78.6(11) . . . . ?
N1 Ir1 N2 C12 2.0(11) . . . . ?
N3 Ir1 N2 C12 94.0(11) . . . . ?
C18 Ir1 N3 C23 -87.6(10) . . . . ?
C33 Ir1 N3 C23 179.6(10) . . . . ?
C11 Ir1 N3 C23 131(2) . . . . ?
N2 Ir1 N3 C23 -8.0(10) . . . . ?
N1 Ir1 N3 C23 89.7(10) . . . . ?
C18 Ir1 N3 C27 97.5(8) . . . . ?
C33 Ir1 N3 C27 4.7(8) . . . . ?
C11 Ir1 N3 C27 -44(3) . . . . ?
N2 Ir1 N3 C27 177.1(8) . . . . ?
N1 Ir1 N3 C27 -85.2(8) . . . . ?
C5 N1 C1 C2 0.0(17) . . . . ?
Ir1 N1 C1 C2 177.0(9) . . . . ?
N1 C1 C2 C3 -0.7(18) . . . . ?
C1 C2 C3 C4 0.4(18) . . . . ?
C2 C3 C4 C5 0.4(18) . . . . ?
C1 N1 C5 C4 0.9(16) . . . . ?
Ir1 N1 C5 C4 -176.6(8) . . . . ?
C1 N1 C5 C6 -179.7(10) . . . . ?
Ir1 N1 C5 C6 2.9(13) . . . . ?
C3 C4 C5 N1 -1.0(17) . . . . ?
C3 C4 C5 C6 179.6(12) . . . . ?
N1 C5 C6 C7 -179.0(11) . . . . ?
C4 C5 C6 C7 0.5(19) . . . . ?
N1 C5 C6 C11 1.1(16) . . . . ?
C4 C5 C6 C11 -179.5(11) . . . . ?
C11 C6 C7 C8 1(2) . . . . ?
C5 C6 C7 C8 -179.2(12) . . . . ?
C6 C7 C8 O1 -176.7(11) . . . . ?
C6 C7 C8 C9 0(2) . . . . ?
C34 O1 C8 C7 -131.4(13) . . . . ?
C34 O1 C8 C9 52.4(18) . . . . ?
C7 C8 C9 C10 1(2) . . . . ?
O1 C8 C9 C10 176.9(12) . . . . ?
C8 C9 C10 C11 -1(2) . . . . ?
C8 C9 C10 O2 179.2(11) . . . . ?
C40 O2 C10 C11 99.1(15) . . . . ?
C40 O2 C10 C9 -81.4(15) . . . . ?
C9 C10 C11 C6 1.5(19) . . . . ?
O2 C10 C11 C6 -179.1(11) . . . . ?
C9 C10 C11 Ir1 -174.2(10) . . . . ?
O2 C10 C11 Ir1 5(2) . . . . ?
C7 C6 C11 C10 -1.2(19) . . . . ?
C5 C6 C11 C10 178.7(11) . . . . ?
C7 C6 C11 Ir1 175.3(10) . . . . ?
C5 C6 C11 Ir1 -4.7(14) . . . . ?
C18 Ir1 C11 C10 -2.5(14) . . . . ?
C33 Ir1 C11 C10 90.7(13) . . . . ?
N2 Ir1 C11 C10 -82.9(13) . . . . ?
N1 Ir1 C11 C10 -179.6(14) . . . . ?
N3 Ir1 C11 C10 138.8(19) . . . . ?
C18 Ir1 C11 C6 -178.2(9) . . . . ?
C33 Ir1 C11 C6 -84.9(9) . . . . ?
N2 Ir1 C11 C6 101.4(9) . . . . ?
N1 Ir1 C11 C6 4.7(9) . . . . ?
N3 Ir1 C11 C6 -37(3) . . . . ?
C16 N2 C12 C13 4(2) . . . . ?
Ir1 N2 C12 C13 -170.9(12) . . . . ?
N2 C12 C13 C14 2(3) . . . . ?
C12 C13 C14 C15 -5(3) . . . . ?
C13 C14 C15 C16 3(3) . . . . ?
C12 N2 C16 C15 -6.3(19) . . . . ?
Ir1 N2 C16 C15 169.5(10) . . . . ?
C12 N2 C16 C17 177.9(12) . . . . ?
Ir1 N2 C16 C17 -6.3(15) . . . . ?
C14 C15 C16 N2 3(2) . . . . ?
C14 C15 C16 C17 177.6(15) . . . . ?
N2 C16 C17 C22 -178.0(12) . . . . ?
C15 C16 C17 C22 7(2) . . . . ?
N2 C16 C17 C18 -0.4(18) . . . . ?
C15 C16 C17 C18 -175.6(14) . . . . ?
C22 C17 C18 C19 2.7(18) . . . . ?
C16 C17 C18 C19 -175.0(11) . . . . ?
C22 C17 C18 Ir1 -175.2(10) . . . . ?
C16 C17 C18 Ir1 7.2(15) . . . . ?
C33 Ir1 C18 C19 -13.4(11) . . . . ?
C11 Ir1 C18 C19 80.1(11) . . . . ?
N2 Ir1 C18 C19 174.7(12) . . . . ?
N1 Ir1 C18 C19 148(8) . . . . ?
N3 Ir1 C18 C19 -92.9(11) . . . . ?
C33 Ir1 C18 C17 164.0(9) . . . . ?
C11 Ir1 C18 C17 -102.4(9) . . . . ?
N2 Ir1 C18 C17 -7.8(9) . . . . ?
N1 Ir1 C18 C17 -35(9) . . . . ?
N3 Ir1 C18 C17 84.5(9) . . . . ?
C17 C18 C19 C20 -3.0(17) . . . . ?
Ir1 C18 C19 C20 174.4(9) . . . . ?
C18 C19 C20 C21 1.8(19) . . . . ?
C19 C20 C21 C22 -0.1(19) . . . . ?
C20 C21 C22 C17 0(2) . . . . ?
C16 C17 C22 C21 176.4(12) . . . . ?
C18 C17 C22 C21 -1(2) . . . . ?
C27 N3 C23 C24 2.2(17) . . . . ?
Ir1 N3 C23 C24 -172.5(9) . . . . ?
N3 C23 C24 C25 -2.3(18) . . . . ?
C23 C24 C25 C26 1.0(18) . . . . ?
C24 C25 C26 C27 0.4(18) . . . . ?
C23 N3 C27 C26 -0.7(16) . . . . ?
Ir1 N3 C27 C26 174.6(8) . . . . ?
C23 N3 C27 C28 178.1(10) . . . . ?
Ir1 N3 C27 C28 -6.6(12) . . . . ?
C25 C26 C27 N3 -0.6(17) . . . . ?
C25 C26 C27 C28 -179.2(11) . . . . ?
N3 C27 C28 C33 5.4(14) . . . . ?
C26 C27 C28 C33 -176.0(11) . . . . ?
N3 C27 C28 C29 -172.3(10) . . . . ?
C26 C27 C28 C29 6.4(18) . . . . ?
C33 C28 C29 C30 0.3(18) . . . . ?
C27 C28 C29 C30 177.9(11) . . . . ?
C28 C29 C30 C31 0.6(18) . . . . ?
C29 C30 C31 C32 -0.6(17) . . . . ?
C30 C31 C32 C33 -0.5(18) . . . . ?
C29 C28 C33 C32 -1.3(16) . . . . ?
C27 C28 C33 C32 -178.9(10) . . . . ?
C29 C28 C33 Ir1 176.4(8) . . . . ?
C27 C28 C33 Ir1 -1.2(13) . . . . ?
C31 C32 C33 C28 1.4(17) . . . . ?
C31 C32 C33 Ir1 -175.9(9) . . . . ?
C18 Ir1 C33 C28 -91.1(8) . . . . ?
C11 Ir1 C33 C28 169.8(9) . . . . ?
N2 Ir1 C33 C28 -45(3) . . . . ?
N1 Ir1 C33 C28 89.9(9) . . . . ?
N3 Ir1 C33 C28 -1.7(8) . . . . ?
C18 Ir1 C33 C32 86.2(11) . . . . ?
C11 Ir1 C33 C32 -12.8(11) . . . . ?
N2 Ir1 C33 C32 133(2) . . . . ?
N1 Ir1 C33 C32 -92.8(11) . . . . ?
N3 Ir1 C33 C32 175.6(11) . . . . ?
C8 O1 C34 C39 -149.7(12) . . . . ?
C8 O1 C34 C35 33.2(18) . . . . ?
C39 C34 C35 C36 3(2) . . . . ?
O1 C34 C35 C36 179.4(11) . . . . ?
C34 C35 C36 C37 0.3(19) . . . . ?
C35 C36 C37 C38 -0.6(19) . . . . ?
C36 C37 C38 C39 -2(2) . . . . ?
C35 C34 C39 C38 -5(2) . . . . ?
O1 C34 C39 C38 178.1(10) . . . . ?
C37 C38 C39 C34 4.4(19) . . . . ?
C10 O2 C40 C41 161.6(13) . . . . ?
C10 O2 C40 C45 -19(2) . . . . ?
O2 C40 C41 C42 173.9(17) . . . . ?
C45 C40 C41 C42 -5(3) . . . . ?
C40 C41 C42 C43 2(3) . . . . ?
C41 C42 C43 C44 -4(4) . . . . ?
C42 C43 C44 C45 8(3) . . . . ?
C43 C44 C45 C40 -11(3) . . . . ?
O2 C40 C45 C44 -169.4(16) . . . . ?
C41 C40 C45 C44 10(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.292
_refine_diff_density_min         -1.347
_refine_diff_density_rms         0.254
