# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bt-C3
_database_code_depnum_ccdc_archive 'CCDC 2355724'
loop_
_audit_author_name
_audit_author_address
'Thomas Teets'
;University of Houston
United States of America
;
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2023-10-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'4(C43 H28 Ir N3 O3 S2), 4(C H2 Cl2), 4(C2), 4[]'
_chemical_formula_sum            'C44 H30 Cl2 Ir N3 O3 S2'
_chemical_formula_weight         975.93
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.1502(17)
_cell_length_b                   24.938(4)
_cell_length_c                   14.546(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.657(2)
_cell_angle_gamma                90
_cell_volume                     3975.0(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    123.20
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.529
_shelx_estimated_absorpt_T_min   0.338
_exptl_absorpt_coefficient_mu    3.643
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1232 before and 0.0372 after correction.
The Ratio of minimum to maximum transmission is 0.6576.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ROCK
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24800
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_min         1.633
_diffrn_ambient_temperature      123.20
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8335
_reflns_number_total             9149
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.396
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         9149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0221P)²+6.7447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0605
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C62(H62), C23(H23), C57(H57), C56(H56), C36(H36), C16(H16), C68(H68),
 C33(H33), C44(H44), C43(H43), C35(H35), C53(H53), C34(H34), C15(H15), C24(H24),
  C69(H69), C65(H65), C25(H25), C46(H46), C55(H55), C14(H14), C45(H45),
 C54(H54), C26(H26), C13(H13)
2.c Idealised Me refined as rotating group:
 C70(H70A,H70B,H70C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.50754(2) 0.35264(2) 0.81060(2) 0.01198(4) Uani 1 1 d . . . . .
S1 S 0.66399(7) 0.45761(3) 0.61115(6) 0.02519(17) Uani 1 1 d . . . . .
S2 S 0.27278(8) 0.33025(4) 1.02852(6) 0.02766(18) Uani 1 1 d . . . . .
Cl2 Cl 0.85488(10) 0.27592(5) 1.13782(7) 0.0503(3) Uani 1 1 d . . . . .
Cl1 Cl 0.95327(13) 0.36185(6) 1.03898(13) 0.0797(4) Uani 1 1 d . . . . .
O2 O 0.13653(18) 0.38752(8) 0.49980(14) 0.0179(4) Uani 1 1 d . . . . .
O1 O 0.62842(18) 0.29281(8) 0.88057(14) 0.0176(4) Uani 1 1 d . . . . .
N3 N 0.4749(2) 0.30004(10) 0.68987(17) 0.0156(5) Uani 1 1 d . . . . .
N2 N 0.3806(2) 0.32457(10) 0.88594(17) 0.0163(5) Uani 1 1 d . . . . .
O3 O -0.0195(2) 0.43432(10) 0.42459(17) 0.0305(5) Uani 1 1 d . . . . .
N1 N 0.6246(2) 0.39039(9) 0.73669(16) 0.0143(5) Uani 1 1 d . . . . .
C31 C 0.5492(3) 0.39912(11) 0.9254(2) 0.0166(6) Uani 1 1 d . . . . .
C63 C 0.2534(3) 0.36784(12) 0.5065(2) 0.0158(6) Uani 1 1 d . . . . .
C11 C 0.3995(2) 0.41245(11) 0.7516(2) 0.0149(6) Uani 1 1 d . . . . .
C22 C 0.7448(3) 0.38062(11) 0.7248(2) 0.0166(6) Uani 1 1 d . . . . .
C32 C 0.4743(3) 0.39122(12) 0.9926(2) 0.0191(6) Uani 1 1 d . . . . .
C41 C 0.3842(3) 0.34993(12) 0.9665(2) 0.0203(6) Uani 1 1 d . . . . .
C62 C 0.3007(3) 0.34163(11) 0.5892(2) 0.0159(6) Uani 1 1 d . . . . .
H62 H 0.252888 0.336810 0.636256 0.019 Uiso 1 1 calc R U . . .
C21 C 0.5738(3) 0.42956(11) 0.6834(2) 0.0165(6) Uani 1 1 d . . . . .
C52 C 0.5970(3) 0.22361(12) 0.7617(2) 0.0206(6) Uani 1 1 d . . . . .
C23 C 0.8259(3) 0.34331(12) 0.7733(2) 0.0217(6) Uani 1 1 d . . . . .
H23 H 0.803132 0.321097 0.820274 0.026 Uiso 1 1 calc R U . . .
C57 C 0.5247(3) 0.25303(12) 0.6871(2) 0.0196(6) Uani 1 1 d . . . . .
H57 H 0.511352 0.236026 0.627606 0.023 Uiso 1 1 calc R U . . .
C51 C 0.6465(3) 0.24452(12) 0.8521(2) 0.0180(6) Uani 1 1 d . . . . .
C47 C 0.2164(3) 0.28490(13) 0.9404(2) 0.0227(6) Uani 1 1 d . . . . .
C67 C 0.3195(3) 0.37455(12) 0.4343(2) 0.0181(6) Uani 1 1 d . . . . .
C61 C 0.4203(3) 0.32245(12) 0.6018(2) 0.0167(6) Uani 1 1 d . . . . .
C56 C 0.7258(3) 0.21020(13) 0.9137(2) 0.0238(7) Uani 1 1 d . . . . .
H56 H 0.761901 0.223190 0.973865 0.029 Uiso 1 1 calc R U . . .
C36 C 0.6417(3) 0.43759(12) 0.9468(2) 0.0215(6) Uani 1 1 d . . . . .
H36 H 0.694658 0.444233 0.903886 0.026 Uiso 1 1 calc R U . . .
C16 C 0.2799(3) 0.42601(12) 0.7615(2) 0.0215(6) Uani 1 1 d . . . . .
H16 H 0.242306 0.406855 0.805025 0.026 Uiso 1 1 calc R U . . .
C68 C 0.4377(3) 0.35324(13) 0.4478(2) 0.0218(6) Uani 1 1 d . . . . .
H68 H 0.484092 0.356267 0.399383 0.026 Uiso 1 1 calc R U . . .
C33 C 0.4880(3) 0.42100(13) 1.0754(2) 0.0260(7) Uani 1 1 d . . . . .
H33 H 0.434162 0.415469 1.118092 0.031 Uiso 1 1 calc R U . . .
C64 C 0.0814(3) 0.41678(12) 0.4232(2) 0.0219(6) Uani 1 1 d . . . . .
C44 C 0.1535(3) 0.22097(13) 0.7849(2) 0.0244(7) Uani 1 1 d . . . . .
H44 H 0.130537 0.198837 0.731369 0.029 Uiso 1 1 calc R U . . .
C43 C 0.2541(3) 0.25450(12) 0.7902(2) 0.0209(6) Uani 1 1 d . . . . .
H43 H 0.300292 0.255103 0.741523 0.025 Uiso 1 1 calc R U . . .
C35 C 0.6569(3) 0.46623(13) 1.0306(2) 0.0274(7) Uani 1 1 d . . . . .
H35 H 0.721160 0.491659 1.044159 0.033 Uiso 1 1 calc R U . . .
C53 C 0.6270(3) 0.17043(13) 0.7397(3) 0.0290(7) Uani 1 1 d . . . . .
H53 H 0.593878 0.156657 0.679495 0.035 Uiso 1 1 calc R U . . .
C12 C 0.4503(3) 0.44496(12) 0.6886(2) 0.0179(6) Uani 1 1 d . . . . .
C34 C 0.5804(3) 0.45851(13) 1.0946(2) 0.0283(7) Uani 1 1 d . . . . .
H34 H 0.591448 0.478736 1.150913 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2160(3) 0.46687(12) 0.7089(2) 0.0245(7) Uani 1 1 d . . . . .
H15 H 0.135172 0.474716 0.716932 0.029 Uiso 1 1 calc R U . . .
C24 C 0.9413(3) 0.33982(14) 0.7503(3) 0.0277(7) Uani 1 1 d . . . . .
H24 H 0.998821 0.315136 0.782856 0.033 Uiso 1 1 calc R U . . .
C66 C 0.2610(3) 0.40302(12) 0.3511(2) 0.0208(6) Uani 1 1 d . . . . .
C42 C 0.2856(3) 0.28722(12) 0.8686(2) 0.0175(6) Uani 1 1 d . . . . .
C69 C 0.4877(3) 0.32795(13) 0.5303(2) 0.0198(6) Uani 1 1 d . . . . .
H69 H 0.568460 0.314183 0.538635 0.024 Uiso 1 1 calc R U . . .
C65 C 0.1484(3) 0.42282(13) 0.3474(2) 0.0233(7) Uani 1 1 d . . . . .
H65 H 0.110917 0.441633 0.292840 0.028 Uiso 1 1 calc R U . . .
C25 C 0.9745(3) 0.37193(15) 0.6800(3) 0.0308(8) Uani 1 1 d . . . . .
H25 H 1.053041 0.367629 0.664433 0.037 Uiso 1 1 calc R U . . .
C46 C 0.1159(3) 0.25042(14) 0.9349(3) 0.0281(7) Uani 1 1 d . . . . .
H46 H 0.070364 0.248862 0.983999 0.034 Uiso 1 1 calc R U . . .
C27 C 0.7812(3) 0.41371(12) 0.6566(2) 0.0197(6) Uani 1 1 d . . . . .
C55 C 0.7518(3) 0.15893(14) 0.8892(3) 0.0318(8) Uani 1 1 d . . . . .
H55 H 0.804941 0.137284 0.932550 0.038 Uiso 1 1 calc R U . . .
C14 C 0.2669(3) 0.49666(13) 0.6448(2) 0.0275(7) Uani 1 1 d . . . . .
H14 H 0.220883 0.523749 0.608157 0.033 Uiso 1 1 calc R U . . .
C45 C 0.0851(3) 0.21900(13) 0.8566(3) 0.0284(8) Uani 1 1 d . . . . .
H45 H 0.016799 0.195674 0.850891 0.034 Uiso 1 1 calc R U . . .
C70 C 0.3281(3) 0.40926(15) 0.2708(2) 0.0287(7) Uani 1 1 d . . . . .
H70A H 0.405032 0.428289 0.292352 0.043 Uiso 1 1 calc R U . . .
H70B H 0.277632 0.429788 0.220567 0.043 Uiso 1 1 calc R U . . .
H70C H 0.345160 0.373775 0.247320 0.043 Uiso 1 1 calc R U . . .
C54 C 0.7015(4) 0.13813(13) 0.8015(3) 0.0340(9) Uani 1 1 d . . . . .
H54 H 0.718498 0.102420 0.785145 0.041 Uiso 1 1 calc R U . . .
C26 C 0.8962(3) 0.40947(14) 0.6333(2) 0.0278(7) Uani 1 1 d . . . . .
H26 H 0.919651 0.431759 0.586696 0.033 Uiso 1 1 calc R U . . .
C13 C 0.3862(3) 0.48593(12) 0.6357(2) 0.0240(7) Uani 1 1 d . . . . .
H13 H 0.423851 0.506335 0.593774 0.029 Uiso 1 1 calc R U . . .
C1 C 0.8209(4) 0.33468(17) 1.0708(3) 0.0434(10) Uani 1 1 d . . . . .
H1A H 0.784074 0.361498 1.107398 0.052 Uiso 1 1 calc R U . . .
H1B H 0.760594 0.326305 1.013644 0.052 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 O1 2.138(2) . ?
Ir1 N3 2.168(2) . ?
Ir1 N2 2.066(2) . ?
Ir1 N1 2.065(2) . ?
Ir1 C31 2.016(3) . ?
Ir1 C11 2.007(3) . ?
S1 C21 1.731(3) . ?
S1 C27 1.739(3) . ?
S2 C41 1.735(3) . ?
S2 C47 1.737(4) . ?
Cl2 C1 1.762(4) . ?
Cl1 C1 1.762(4) . ?
O2 C63 1.379(3) . ?
O2 C64 1.378(4) . ?
O1 C51 1.301(4) . ?
N3 C57 1.301(4) . ?
N3 C61 1.427(4) . ?
N2 C41 1.326(4) . ?
N2 C42 1.398(4) . ?
O3 C64 1.211(4) . ?
N1 C22 1.403(4) . ?
N1 C21 1.309(4) . ?
C31 C32 1.412(4) . ?
C31 C36 1.401(4) . ?
C63 C62 1.385(4) . ?
C63 C67 1.399(4) . ?
C11 C16 1.409(4) . ?
C11 C12 1.418(4) . ?
C22 C23 1.395(4) . ?
C22 C27 1.407(4) . ?
C32 C41 1.440(4) . ?
C32 C33 1.399(4) . ?
C62 H62 0.9500 . ?
C62 C61 1.396(4) . ?
C21 C12 1.445(4) . ?
C52 C57 1.429(4) . ?
C52 C51 1.427(4) . ?
C52 C53 1.419(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(4) . ?
C57 H57 0.9500 . ?
C51 C56 1.422(4) . ?
C47 C42 1.410(4) . ?
C47 C46 1.403(4) . ?
C67 C68 1.402(4) . ?
C67 C66 1.451(4) . ?
C61 C69 1.398(4) . ?
C56 H56 0.9500 . ?
C56 C55 1.373(5) . ?
C36 H36 0.9500 . ?
C36 C35 1.396(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.389(4) . ?
C68 H68 0.9500 . ?
C68 C69 1.379(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.382(5) . ?
C64 C65 1.448(4) . ?
C44 H44 0.9500 . ?
C44 C43 1.389(4) . ?
C44 C45 1.402(5) . ?
C43 H43 0.9500 . ?
C43 C42 1.393(4) . ?
C35 H35 0.9500 . ?
C35 C34 1.387(5) . ?
C53 H53 0.9500 . ?
C53 C54 1.368(5) . ?
C12 C13 1.394(4) . ?
C34 H34 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.392(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.401(5) . ?
C66 C65 1.341(4) . ?
C66 C70 1.506(4) . ?
C69 H69 0.9500 . ?
C65 H65 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.372(5) . ?
C46 H46 0.9500 . ?
C46 C45 1.373(5) . ?
C27 C26 1.389(4) . ?
C55 H55 0.9500 . ?
C55 C54 1.394(6) . ?
C14 H14 0.9500 . ?
C14 C13 1.387(5) . ?
C45 H45 0.9500 . ?
C70 H70A 0.9800 . ?
C70 H70B 0.9800 . ?
C70 H70C 0.9800 . ?
C54 H54 0.9500 . ?
C26 H26 0.9500 . ?
C13 H13 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

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 N3 87.71(8) . . ?
N2 Ir1 O1 86.82(9) . . ?
N2 Ir1 N3 101.30(9) . . ?
N1 Ir1 O1 99.34(8) . . ?
N1 Ir1 N3 83.20(9) . . ?
N1 Ir1 N2 172.57(9) . . ?
C31 Ir1 O1 88.77(10) . . ?
C31 Ir1 N3 176.07(10) . . ?
C31 Ir1 N2 80.24(11) . . ?
C31 Ir1 N1 95.65(11) . . ?
C11 Ir1 O1 176.05(10) . . ?
C11 Ir1 N3 96.05(10) . . ?
C11 Ir1 N2 93.60(10) . . ?
C11 Ir1 N1 79.96(10) . . ?
C11 Ir1 C31 87.43(11) . . ?
C21 S1 C27 89.72(14) . . ?
C41 S2 C47 89.84(15) . . ?
C64 O2 C63 121.3(2) . . ?
C51 O1 Ir1 128.01(19) . . ?
C57 N3 Ir1 124.2(2) . . ?
C57 N3 C61 116.0(2) . . ?
C61 N3 Ir1 118.05(18) . . ?
C41 N2 Ir1 113.31(19) . . ?
C41 N2 C42 112.0(2) . . ?
C42 N2 Ir1 134.5(2) . . ?
C22 N1 Ir1 134.00(19) . . ?
C21 N1 Ir1 113.73(19) . . ?
C21 N1 C22 112.0(2) . . ?
C32 C31 Ir1 114.7(2) . . ?
C36 C31 Ir1 128.7(2) . . ?
C36 C31 C32 116.6(3) . . ?
O2 C63 C62 115.6(2) . . ?
O2 C63 C67 121.7(3) . . ?
C62 C63 C67 122.6(3) . . ?
C16 C11 Ir1 129.7(2) . . ?
C16 C11 C12 115.3(3) . . ?
C12 C11 Ir1 114.9(2) . . ?
N1 C22 C27 113.1(3) . . ?
C23 C22 N1 126.7(3) . . ?
C23 C22 C27 120.2(3) . . ?
C31 C32 C41 113.0(3) . . ?
C33 C32 C31 122.5(3) . . ?
C33 C32 C41 124.5(3) . . ?
N2 C41 S2 114.6(2) . . ?
N2 C41 C32 118.7(3) . . ?
C32 C41 S2 126.6(2) . . ?
C63 C62 H62 120.8 . . ?
C63 C62 C61 118.5(3) . . ?
C61 C62 H62 120.8 . . ?
N1 C21 S1 115.1(2) . . ?
N1 C21 C12 118.7(3) . . ?
C12 C21 S1 126.2(2) . . ?
C51 C52 C57 125.5(3) . . ?
C53 C52 C57 115.6(3) . . ?
C53 C52 C51 118.8(3) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 C22 117.5(3) . . ?
C24 C23 H23 121.2 . . ?
N3 C57 C52 128.5(3) . . ?
N3 C57 H57 115.8 . . ?
C52 C57 H57 115.8 . . ?
O1 C51 C52 125.1(3) . . ?
O1 C51 C56 118.1(3) . . ?
C56 C51 C52 116.7(3) . . ?
C42 C47 S2 110.3(2) . . ?
C46 C47 S2 128.1(3) . . ?
C46 C47 C42 121.6(3) . . ?
C63 C67 C68 117.5(3) . . ?
C63 C67 C66 117.9(3) . . ?
C68 C67 C66 124.6(3) . . ?
C62 C61 N3 119.4(3) . . ?
C62 C61 C69 120.0(3) . . ?
C69 C61 N3 120.5(3) . . ?
C51 C56 H56 118.9 . . ?
C55 C56 C51 122.2(3) . . ?
C55 C56 H56 118.9 . . ?
C31 C36 H36 119.7 . . ?
C35 C36 C31 120.6(3) . . ?
C35 C36 H36 119.7 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C67 C68 H68 119.6 . . ?
C69 C68 C67 120.9(3) . . ?
C69 C68 H68 119.6 . . ?
C32 C33 H33 120.2 . . ?
C34 C33 C32 119.5(3) . . ?
C34 C33 H33 120.2 . . ?
O2 C64 C65 117.0(3) . . ?
O3 C64 O2 117.0(3) . . ?
O3 C64 C65 125.9(3) . . ?
C43 C44 H44 119.2 . . ?
C43 C44 C45 121.6(3) . . ?
C45 C44 H44 119.2 . . ?
C44 C43 H43 120.8 . . ?
C44 C43 C42 118.5(3) . . ?
C42 C43 H43 120.8 . . ?
C36 C35 H35 119.2 . . ?
C34 C35 C36 121.7(3) . . ?
C34 C35 H35 119.2 . . ?
C52 C53 H53 118.6 . . ?
C54 C53 C52 122.8(3) . . ?
C54 C53 H53 118.6 . . ?
C11 C12 C21 112.3(2) . . ?
C13 C12 C11 123.4(3) . . ?
C13 C12 C21 124.2(3) . . ?
C33 C34 C35 119.1(3) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 H34 120.5 . . ?
C16 C15 H15 119.0 . . ?
C16 C15 C14 121.9(3) . . ?
C14 C15 H15 119.0 . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.4(3) . . ?
C25 C24 H24 119.3 . . ?
C67 C66 C70 119.1(3) . . ?
C65 C66 C67 119.1(3) . . ?
C65 C66 C70 121.8(3) . . ?
N2 C42 C47 113.2(3) . . ?
C43 C42 N2 127.3(3) . . ?
C43 C42 C47 119.5(3) . . ?
C61 C69 H69 119.8 . . ?
C68 C69 C61 120.4(3) . . ?
C68 C69 H69 119.8 . . ?
C64 C65 H65 118.6 . . ?
C66 C65 C64 122.8(3) . . ?
C66 C65 H65 118.6 . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.4(3) . . ?
C26 C25 H25 119.3 . . ?
C47 C46 H46 120.9 . . ?
C45 C46 C47 118.1(3) . . ?
C45 C46 H46 120.9 . . ?
C22 C27 S1 110.0(2) . . ?
C26 C27 S1 128.1(2) . . ?
C26 C27 C22 121.8(3) . . ?
C56 C55 H55 119.5 . . ?
C56 C55 C54 121.0(3) . . ?
C54 C55 H55 119.5 . . ?
C15 C14 H14 120.7 . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 H14 120.7 . . ?
C44 C45 H45 119.6 . . ?
C46 C45 C44 120.7(3) . . ?
C46 C45 H45 119.6 . . ?
C66 C70 H70A 109.5 . . ?
C66 C70 H70B 109.5 . . ?
C66 C70 H70C 109.5 . . ?
H70A C70 H70B 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
C53 C54 C55 118.3(3) . . ?
C53 C54 H54 120.8 . . ?
C55 C54 H54 120.8 . . ?
C25 C26 C27 117.6(3) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.3 . . ?
Cl2 C1 Cl1 111.1(2) . . ?
Cl2 C1 H1A 109.4 . . ?
Cl2 C1 H1B 109.4 . . ?
Cl1 C1 H1A 109.4 . . ?
Cl1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?

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
Ir1 O1 C51 C52 7.1(4) . . . . ?
Ir1 O1 C51 C56 -175.72(19) . . . . ?
Ir1 N3 C57 C52 7.9(4) . . . . ?
Ir1 N3 C61 C62 -65.5(3) . . . . ?
Ir1 N3 C61 C69 110.9(3) . . . . ?
Ir1 N2 C41 S2 176.27(14) . . . . ?
Ir1 N2 C41 C32 -1.7(3) . . . . ?
Ir1 N2 C42 C47 -175.1(2) . . . . ?
Ir1 N2 C42 C43 3.9(5) . . . . ?
Ir1 N1 C22 C23 -8.9(5) . . . . ?
Ir1 N1 C22 C27 171.8(2) . . . . ?
Ir1 N1 C21 S1 -173.54(13) . . . . ?
Ir1 N1 C21 C12 5.7(3) . . . . ?
Ir1 C31 C32 C41 1.7(3) . . . . ?
Ir1 C31 C32 C33 -178.3(2) . . . . ?
Ir1 C31 C36 C35 179.9(2) . . . . ?
Ir1 C11 C16 C15 -175.1(2) . . . . ?
Ir1 C11 C12 C21 -2.9(3) . . . . ?
Ir1 C11 C12 C13 175.2(2) . . . . ?
S1 C21 C12 C11 177.2(2) . . . . ?
S1 C21 C12 C13 -0.9(4) . . . . ?
S1 C27 C26 C25 179.1(3) . . . . ?
S2 C47 C42 N2 0.2(3) . . . . ?
S2 C47 C42 C43 -179.0(2) . . . . ?
S2 C47 C46 C45 177.8(3) . . . . ?
O2 C63 C62 C61 -177.7(2) . . . . ?
O2 C63 C67 C68 179.8(3) . . . . ?
O2 C63 C67 C66 -0.2(4) . . . . ?
O2 C64 C65 C66 -2.4(5) . . . . ?
O1 C51 C56 C55 -178.9(3) . . . . ?
N3 C61 C69 C68 -175.1(3) . . . . ?
O3 C64 C65 C66 178.9(3) . . . . ?
N1 C22 C23 C24 179.7(3) . . . . ?
N1 C22 C27 S1 1.5(3) . . . . ?
N1 C22 C27 C26 -178.7(3) . . . . ?
N1 C21 C12 C11 -2.0(4) . . . . ?
N1 C21 C12 C13 179.9(3) . . . . ?
C31 C32 C41 S2 -177.6(2) . . . . ?
C31 C32 C41 N2 0.0(4) . . . . ?
C31 C32 C33 C34 -2.2(5) . . . . ?
C31 C36 C35 C34 -1.1(5) . . . . ?
C63 O2 C64 O3 -177.2(3) . . . . ?
C63 O2 C64 C65 4.0(4) . . . . ?
C63 C62 C61 N3 173.9(3) . . . . ?
C63 C62 C61 C69 -2.6(4) . . . . ?
C63 C67 C68 C69 -1.7(4) . . . . ?
C63 C67 C66 C65 1.7(4) . . . . ?
C63 C67 C66 C70 -177.9(3) . . . . ?
C11 C16 C15 C14 -0.7(5) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C22 N1 C21 S1 1.6(3) . . . . ?
C22 N1 C21 C12 -179.2(2) . . . . ?
C22 C23 C24 C25 -1.0(5) . . . . ?
C22 C27 C26 C25 -0.6(5) . . . . ?
C32 C31 C36 C35 -0.2(4) . . . . ?
C32 C33 C34 C35 0.7(5) . . . . ?
C41 S2 C47 C42 0.0(2) . . . . ?
C41 S2 C47 C46 -178.7(3) . . . . ?
C41 N2 C42 C47 -0.3(4) . . . . ?
C41 N2 C42 C43 178.7(3) . . . . ?
C41 C32 C33 C34 177.9(3) . . . . ?
C62 C63 C67 C68 0.4(4) . . . . ?
C62 C63 C67 C66 -179.6(3) . . . . ?
C62 C61 C69 C68 1.3(5) . . . . ?
C21 S1 C27 C22 -0.5(2) . . . . ?
C21 S1 C27 C26 179.7(3) . . . . ?
C21 N1 C22 C23 177.3(3) . . . . ?
C21 N1 C22 C27 -2.0(4) . . . . ?
C21 C12 C13 C14 178.7(3) . . . . ?
C52 C51 C56 C55 -1.5(4) . . . . ?
C52 C53 C54 C55 -1.3(5) . . . . ?
C23 C22 C27 S1 -177.8(2) . . . . ?
C23 C22 C27 C26 1.9(5) . . . . ?
C23 C24 C25 C26 2.3(6) . . . . ?
C57 N3 C61 C62 128.9(3) . . . . ?
C57 N3 C61 C69 -54.6(4) . . . . ?
C57 C52 C51 O1 3.1(5) . . . . ?
C57 C52 C51 C56 -174.1(3) . . . . ?
C57 C52 C53 C54 175.9(3) . . . . ?
C51 C52 C57 N3 -11.6(5) . . . . ?
C51 C52 C53 C54 0.1(5) . . . . ?
C51 C56 C55 C54 0.3(5) . . . . ?
C47 S2 C41 N2 -0.2(2) . . . . ?
C47 S2 C41 C32 177.5(3) . . . . ?
C47 C46 C45 C44 0.8(5) . . . . ?
C67 C63 C62 C61 1.7(4) . . . . ?
C67 C68 C69 C61 0.9(5) . . . . ?
C67 C66 C65 C64 -0.4(5) . . . . ?
C61 N3 C57 C52 172.5(3) . . . . ?
C56 C55 C54 C53 1.1(5) . . . . ?
C36 C31 C32 C41 -178.2(3) . . . . ?
C36 C31 C32 C33 1.9(4) . . . . ?
C36 C35 C34 C33 0.9(5) . . . . ?
C16 C11 C12 C21 178.7(3) . . . . ?
C16 C11 C12 C13 -3.2(4) . . . . ?
C16 C15 C14 C13 -1.9(5) . . . . ?
C68 C67 C66 C65 -178.2(3) . . . . ?
C68 C67 C66 C70 2.1(5) . . . . ?
C33 C32 C41 S2 2.3(5) . . . . ?
C33 C32 C41 N2 180.0(3) . . . . ?
C64 O2 C63 C62 176.6(3) . . . . ?
C64 O2 C63 C67 -2.8(4) . . . . ?
C44 C43 C42 N2 -178.0(3) . . . . ?
C44 C43 C42 C47 0.9(4) . . . . ?
C43 C44 C45 C46 0.0(5) . . . . ?
C53 C52 C57 N3 172.8(3) . . . . ?
C53 C52 C51 O1 178.5(3) . . . . ?
C53 C52 C51 C56 1.3(4) . . . . ?
C12 C11 C16 C15 3.1(4) . . . . ?
C15 C14 C13 C12 1.8(5) . . . . ?
C24 C25 C26 C27 -1.5(5) . . . . ?
C66 C67 C68 C69 178.2(3) . . . . ?
C42 N2 C41 S2 0.3(3) . . . . ?
C42 N2 C41 C32 -177.6(3) . . . . ?
C42 C47 C46 C45 -0.7(5) . . . . ?
C46 C47 C42 N2 178.9(3) . . . . ?
C46 C47 C42 C43 -0.2(5) . . . . ?
C27 S1 C21 N1 -0.6(2) . . . . ?
C27 S1 C21 C12 -179.8(3) . . . . ?
C27 C22 C23 C24 -1.1(5) . . . . ?
C45 C44 C43 C42 -0.8(5) . . . . ?
C70 C66 C65 C64 179.2(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 173.9 39.2 ?
2 0.000 0.500 0.000 173.9 39.2 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_platon_squeeze_void_probe_radius 1.20
_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_bt-C4
_database_code_depnum_ccdc_archive 'CCDC 2355725'
loop_
_audit_author_name
_audit_author_address
'Thomas Teets'
;University of Houston
United States of America
;
_audit_update_record             
;
2024-06-20 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H29 Ir N4 O3 S2'
_chemical_formula_weight         906.02

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   15.564(2)
_cell_length_b                   14.1664(19)
_cell_length_c                   15.798(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.365(2)
_cell_angle_gamma                90
_cell_volume                     3426.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.53

_exptl_crystal_description       Rock
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.069
_shelx_estimated_absorpt_T_min   0.375
_shelx_estimated_absorpt_T_max   0.497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20884
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.691
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7877
_reflns_number_gt                7046
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.9837P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7877
_refine_ls_number_parameters     482
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0619
_refine_ls_wR_factor_gt          0.0600
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.63108(2) 0.42165(2) 0.25355(2) 0.01223(4) Uani 1 1 d . . . . .
S1 S 0.37984(5) 0.46722(5) 0.06694(5) 0.02227(16) Uani 1 1 d . . . . .
S2 S 0.91724(5) 0.48989(6) 0.32319(5) 0.02268(16) Uani 1 1 d . . . . .
O1 O 0.64349(13) 0.28142(13) 0.30408(12) 0.0171(4) Uani 1 1 d . . . . .
O2 O 0.22990(14) 0.44265(14) 0.25454(14) 0.0230(5) Uani 1 1 d . . . . .
O3 O 0.09332(15) 0.39352(17) 0.22512(15) 0.0292(5) Uani 1 1 d . . . . .
N1 N 0.51418(15) 0.40034(16) 0.16975(15) 0.0153(5) Uani 1 1 d . . . . .
N2 N 0.75313(15) 0.45827(16) 0.32121(14) 0.0146(5) Uani 1 1 d . . . . .
N3 N 0.55816(15) 0.45360(16) 0.35175(15) 0.0153(5) Uani 1 1 d . . . . .
N4 N 0.52358(16) 0.54653(17) 0.35809(16) 0.0192(5) Uani 1 1 d D . . . .
H4 H 0.557(2) 0.5834(19) 0.335(2) 0.023 Uiso 1 1 d D U . . .
C1 C 0.54482(19) 0.3983(2) 0.41343(18) 0.0182(6) Uani 1 1 d . . . . .
H1A H 0.514686 0.424809 0.454971 0.022 Uiso 1 1 calc R U . . .
C11 C 0.47747(19) 0.2288(2) 0.16755(18) 0.0193(6) Uani 1 1 d . . . . .
H11A H 0.530993 0.210643 0.202712 0.023 Uiso 1 1 calc R U . . .
C12 C 0.4143(2) 0.1623(2) 0.13538(19) 0.0231(6) Uani 1 1 d . . . . .
H12A H 0.425471 0.097578 0.148767 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3357(2) 0.1874(2) 0.0844(2) 0.0259(7) Uani 1 1 d . . . . .
H13A H 0.293719 0.139917 0.064889 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3173(2) 0.2802(2) 0.06162(19) 0.0248(7) Uani 1 1 d . . . . .
H14A H 0.263367 0.297519 0.026733 0.030 Uiso 1 1 calc R U . . .
C15 C 0.38072(18) 0.3474(2) 0.09159(17) 0.0180(6) Uani 1 1 d . . . . .
C16 C 0.45952(18) 0.32283(19) 0.14645(17) 0.0157(6) Uani 1 1 d . . . . .
C21 C 0.61496(19) 0.55073(19) 0.19963(17) 0.0158(6) Uani 1 1 d . . . . .
C22 C 0.67088(19) 0.62840(19) 0.21002(18) 0.0185(6) Uani 1 1 d . . . . .
H22A H 0.725409 0.623773 0.248085 0.022 Uiso 1 1 calc R U . . .
C23 C 0.6488(2) 0.7125(2) 0.1660(2) 0.0235(7) Uani 1 1 d . . . . .
H23A H 0.689695 0.762901 0.172460 0.028 Uiso 1 1 calc R U . . .
C24 C 0.5678(2) 0.7242(2) 0.11268(19) 0.0239(7) Uani 1 1 d . . . . .
H24A H 0.552549 0.782858 0.084831 0.029 Uiso 1 1 calc R U . . .
C25 C 0.5103(2) 0.6494(2) 0.10099(19) 0.0224(6) Uani 1 1 d . . . . .
H25A H 0.454891 0.655864 0.064777 0.027 Uiso 1 1 calc R U . . .
C26 C 0.5342(2) 0.56373(19) 0.14284(18) 0.0175(6) Uani 1 1 d . . . . .
C27 C 0.48124(18) 0.4788(2) 0.13099(17) 0.0165(6) Uani 1 1 d . . . . .
C31 C 0.73727(19) 0.5292(2) 0.46358(18) 0.0195(6) Uani 1 1 d . . . . .
H31A H 0.676841 0.514731 0.457157 0.023 Uiso 1 1 calc R U . . .
C32 C 0.7801(2) 0.57429(19) 0.53679(19) 0.0215(7) Uani 1 1 d . . . . .
H32A H 0.748665 0.589758 0.581201 0.026 Uiso 1 1 calc R U . . .
C33 C 0.8683(2) 0.5975(2) 0.54677(19) 0.0232(7) Uani 1 1 d . . . . .
H33A H 0.896090 0.628788 0.597558 0.028 Uiso 1 1 calc R U . . .
C34 C 0.9152(2) 0.5757(2) 0.4842(2) 0.0237(7) Uani 1 1 d . . . . .
H34A H 0.975188 0.592305 0.490379 0.028 Uiso 1 1 calc R U . . .
C35 C 0.87274(19) 0.5281(2) 0.41042(18) 0.0186(6) Uani 1 1 d . . . . .
C36 C 0.78427(18) 0.50527(19) 0.39919(17) 0.0150(6) Uani 1 1 d . . . . .
C41 C 0.70571(18) 0.3833(2) 0.16744(17) 0.0149(5) Uani 1 1 d . . . . .
C42 C 0.6812(2) 0.3368(2) 0.08899(18) 0.0207(6) Uani 1 1 d . . . . .
H42A H 0.621817 0.319682 0.070370 0.025 Uiso 1 1 calc R U . . .
C43 C 0.7421(2) 0.3152(2) 0.03765(19) 0.0255(7) Uani 1 1 d . . . . .
H43A H 0.723007 0.285889 -0.016551 0.031 Uiso 1 1 calc R U . . .
C44 C 0.8302(2) 0.3354(2) 0.0635(2) 0.0272(7) Uani 1 1 d . . . . .
H44A H 0.871078 0.319585 0.027799 0.033 Uiso 1 1 calc R U . . .
C45 C 0.8576(2) 0.3789(2) 0.14223(19) 0.0227(6) Uani 1 1 d . . . . .
H45A H 0.917722 0.392331 0.161764 0.027 Uiso 1 1 calc R U . . .
C46 C 0.79584(19) 0.40259(19) 0.19230(18) 0.0172(6) Uani 1 1 d . . . . .
C47 C 0.81647(19) 0.4465(2) 0.27632(18) 0.0173(6) Uani 1 1 d . . . . .
C51 C 0.61585(18) 0.24864(19) 0.37001(17) 0.0159(6) Uani 1 1 d . . . . .
C52 C 0.62986(19) 0.1509(2) 0.39012(18) 0.0205(6) Uani 1 1 d . . . . .
H52A H 0.658383 0.113025 0.353923 0.025 Uiso 1 1 calc R U . . .
C53 C 0.6035(2) 0.1095(2) 0.4601(2) 0.0253(7) Uani 1 1 d . . . . .
H53A H 0.613893 0.044144 0.471124 0.030 Uiso 1 1 calc R U . . .
C54 C 0.5616(2) 0.1626(2) 0.51511(19) 0.0274(7) Uani 1 1 d . . . . .
H54A H 0.544044 0.134113 0.563707 0.033 Uiso 1 1 calc R U . . .
C55 C 0.5463(2) 0.2558(2) 0.49800(18) 0.0237(7) Uani 1 1 d . . . . .
H55A H 0.518210 0.291935 0.535778 0.028 Uiso 1 1 calc R U . . .
C56 C 0.57070(18) 0.3010(2) 0.42580(18) 0.0181(6) Uani 1 1 d . . . . .
C61 C 0.4374(2) 0.5623(2) 0.31480(18) 0.0181(6) Uani 1 1 d . . . . .
C62 C 0.37429(19) 0.4921(2) 0.30332(18) 0.0196(6) Uani 1 1 d . . . . .
H62A H 0.388426 0.429366 0.322182 0.024 Uiso 1 1 calc R U . . .
C63 C 0.29013(19) 0.5154(2) 0.26369(18) 0.0191(6) Uani 1 1 d . . . . .
C64 C 0.1422(2) 0.4584(2) 0.22087(19) 0.0235(7) Uani 1 1 d . . . . .
C65 C 0.1198(2) 0.5504(2) 0.1860(2) 0.0264(7) Uani 1 1 d . . . . .
H65A H 0.062117 0.560571 0.155614 0.032 Uiso 1 1 calc R U . . .
C66 C 0.1765(2) 0.6231(2) 0.19412(19) 0.0252(7) Uani 1 1 d . . . . .
C67 C 0.2663(2) 0.6064(2) 0.23525(18) 0.0205(6) Uani 1 1 d . . . . .
C68 C 0.3316(2) 0.6763(2) 0.24833(19) 0.0240(7) Uani 1 1 d . . . . .
H68A H 0.317530 0.739086 0.229762 0.029 Uiso 1 1 calc R U . . .
C69 C 0.4150(2) 0.6549(2) 0.28745(19) 0.0220(6) Uani 1 1 d . . . . .
H69A H 0.458144 0.703061 0.296214 0.026 Uiso 1 1 calc R U . . .
C70 C 0.1495(2) 0.7214(2) 0.1661(2) 0.0308(7) Uani 1 1 d . . . . .
H70A H 0.087055 0.722275 0.141557 0.046 Uiso 1 1 calc R U . . .
H70B H 0.182989 0.742473 0.122639 0.046 Uiso 1 1 calc R U . . .
H70C H 0.160906 0.763901 0.215854 0.046 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 C21 2.014(3) . ?
Ir1 C41 2.016(3) . ?
Ir1 N1 2.071(2) . ?
Ir1 N2 2.071(2) . ?
Ir1 N3 2.129(2) . ?
Ir1 O1 2.1366(18) . ?
S1 C27 1.722(3) . ?
S1 C15 1.740(3) . ?
S2 C47 1.723(3) . ?
S2 C35 1.736(3) . ?
O1 C51 1.283(3) . ?
O2 C63 1.383(3) . ?
O2 C64 1.391(4) . ?
O3 C64 1.202(4) . ?
N1 C27 1.326(3) . ?
N1 C16 1.397(3) . ?
N2 C47 1.325(4) . ?
N2 C36 1.407(3) . ?
N3 C1 1.296(4) . ?
N3 N4 1.433(3) . ?
N4 C61 1.410(4) . ?
C1 C56 1.439(4) . ?
C11 C16 1.389(4) . ?
C11 C12 1.390(4) . ?
C12 C13 1.384(4) . ?
C13 C14 1.379(4) . ?
C14 C15 1.392(4) . ?
C15 C16 1.412(4) . ?
C21 C22 1.394(4) . ?
C21 C26 1.419(4) . ?
C22 C23 1.391(4) . ?
C23 C24 1.394(4) . ?
C24 C25 1.378(4) . ?
C25 C26 1.400(4) . ?
C26 C27 1.452(4) . ?
C31 C32 1.383(4) . ?
C31 C36 1.397(4) . ?
C32 C33 1.393(5) . ?
C33 C34 1.367(5) . ?
C34 C35 1.405(4) . ?
C35 C36 1.394(4) . ?
C41 C42 1.395(4) . ?
C41 C46 1.414(4) . ?
C42 C43 1.388(4) . ?
C43 C44 1.389(4) . ?
C44 C45 1.384(4) . ?
C45 C46 1.392(4) . ?
C46 C47 1.448(4) . ?
C51 C52 1.429(4) . ?
C51 C56 1.430(4) . ?
C52 C53 1.378(4) . ?
C53 C54 1.396(5) . ?
C54 C55 1.360(4) . ?
C55 C56 1.418(4) . ?
C61 C62 1.387(4) . ?
C61 C69 1.405(4) . ?
C62 C63 1.386(4) . ?
C63 C67 1.393(4) . ?
C64 C65 1.433(5) . ?
C65 C66 1.347(5) . ?
C66 C67 1.450(4) . ?
C66 C70 1.499(4) . ?
C67 C68 1.407(4) . ?
C68 C69 1.368(4) . ?

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
C21 Ir1 C41 90.12(11) . . ?
C21 Ir1 N1 80.42(10) . . ?
C41 Ir1 N1 94.35(10) . . ?
C21 Ir1 N2 91.36(10) . . ?
C41 Ir1 N2 80.18(10) . . ?
N1 Ir1 N2 170.17(9) . . ?
C21 Ir1 N3 94.19(10) . . ?
C41 Ir1 N3 175.16(9) . . ?
N1 Ir1 N3 88.54(9) . . ?
N2 Ir1 N3 97.49(9) . . ?
C21 Ir1 O1 176.62(9) . . ?
C41 Ir1 O1 88.70(9) . . ?
N1 Ir1 O1 96.50(8) . . ?
N2 Ir1 O1 91.56(8) . . ?
N3 Ir1 O1 87.11(8) . . ?
C27 S1 C15 89.52(13) . . ?
C47 S2 C35 89.43(14) . . ?
C51 O1 Ir1 128.22(17) . . ?
C63 O2 C64 121.4(2) . . ?
C27 N1 C16 111.7(2) . . ?
C27 N1 Ir1 113.28(18) . . ?
C16 N1 Ir1 134.94(19) . . ?
C47 N2 C36 110.9(2) . . ?
C47 N2 Ir1 113.20(18) . . ?
C36 N2 Ir1 135.21(19) . . ?
C1 N3 N4 113.0(2) . . ?
C1 N3 Ir1 126.7(2) . . ?
N4 N3 Ir1 120.16(17) . . ?
C61 N4 N3 116.7(2) . . ?
N3 C1 C56 127.0(3) . . ?
C16 C11 C12 117.6(3) . . ?
C13 C12 C11 122.1(3) . . ?
C14 C13 C12 121.1(3) . . ?
C13 C14 C15 117.5(3) . . ?
C14 C15 C16 121.6(3) . . ?
C14 C15 S1 127.9(2) . . ?
C16 C15 S1 110.4(2) . . ?
C11 C16 N1 127.1(3) . . ?
C11 C16 C15 119.9(3) . . ?
N1 C16 C15 112.8(2) . . ?
C22 C21 C26 115.8(3) . . ?
C22 C21 Ir1 129.7(2) . . ?
C26 C21 Ir1 114.5(2) . . ?
C23 C22 C21 121.6(3) . . ?
C22 C23 C24 121.3(3) . . ?
C25 C24 C23 118.9(3) . . ?
C24 C25 C26 119.5(3) . . ?
C25 C26 C21 122.7(3) . . ?
C25 C26 C27 124.2(3) . . ?
C21 C26 C27 113.1(2) . . ?
N1 C27 C26 118.1(2) . . ?
N1 C27 S1 115.4(2) . . ?
C26 C27 S1 126.4(2) . . ?
C32 C31 C36 119.0(3) . . ?
C31 C32 C33 121.4(3) . . ?
C34 C33 C32 120.6(3) . . ?
C33 C34 C35 118.4(3) . . ?
C36 C35 C34 121.6(3) . . ?
C36 C35 S2 110.7(2) . . ?
C34 C35 S2 127.8(2) . . ?
C35 C36 C31 119.0(2) . . ?
C35 C36 N2 113.4(2) . . ?
C31 C36 N2 127.5(3) . . ?
C42 C41 C46 115.9(3) . . ?
C42 C41 Ir1 128.9(2) . . ?
C46 C41 Ir1 115.08(19) . . ?
C43 C42 C41 121.2(3) . . ?
C42 C43 C44 121.6(3) . . ?
C45 C44 C43 119.0(3) . . ?
C44 C45 C46 119.0(3) . . ?
C45 C46 C41 123.2(3) . . ?
C45 C46 C47 124.2(3) . . ?
C41 C46 C47 112.5(3) . . ?
N2 C47 C46 118.8(3) . . ?
N2 C47 S2 115.6(2) . . ?
C46 C47 S2 125.6(2) . . ?
O1 C51 C52 118.1(3) . . ?
O1 C51 C56 125.9(3) . . ?
C52 C51 C56 116.0(3) . . ?
C53 C52 C51 122.4(3) . . ?
C52 C53 C54 120.6(3) . . ?
C55 C54 C53 119.0(3) . . ?
C54 C55 C56 122.4(3) . . ?
C55 C56 C51 119.6(3) . . ?
C55 C56 C1 115.6(3) . . ?
C51 C56 C1 124.7(3) . . ?
C62 C61 C69 119.9(3) . . ?
C62 C61 N4 122.6(3) . . ?
C69 C61 N4 117.3(3) . . ?
C63 C62 C61 118.5(3) . . ?
O2 C63 C62 115.9(3) . . ?
O2 C63 C67 121.3(3) . . ?
C62 C63 C67 122.8(3) . . ?
O3 C64 O2 116.3(3) . . ?
O3 C64 C65 127.1(3) . . ?
O2 C64 C65 116.5(3) . . ?
C66 C65 C64 123.3(3) . . ?
C65 C66 C67 118.7(3) . . ?
C65 C66 C70 122.6(3) . . ?
C67 C66 C70 118.7(3) . . ?
C63 C67 C68 117.4(3) . . ?
C63 C67 C66 118.3(3) . . ?
C68 C67 C66 124.3(3) . . ?
C69 C68 C67 120.8(3) . . ?
C68 C69 C61 120.6(3) . . ?

_refine_diff_density_max         1.787
_refine_diff_density_min         -1.251
_refine_diff_density_rms         0.105



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_piq-C3
_database_code_depnum_ccdc_archive 'CCDC 2355726'
loop_
_audit_author_name
_audit_author_address
'Thomas Teets'
;University of Houston
United States of America
;
_audit_update_record             
;
2024-05-15 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C47 H32 Ir N3 O3'
_chemical_formula_weight         878.95

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   17.873(5)
_cell_length_b                   10.022(3)
_cell_length_c                   19.645(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.260(4)
_cell_angle_gamma                90
_cell_volume                     3462.6(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3009
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      22.99

_exptl_crystal_description       rock
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    3.907
_shelx_estimated_absorpt_T_min   0.368
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4966
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20396
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.699
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7606
_reflns_number_gt                5846
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)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         7606
_refine_ls_number_parameters     488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.54486(2) 0.31785(2) 0.26512(2) 0.01514(7) Uani 1 1 d . . . . .
O1 O 0.5007(2) 0.5101(3) 0.23489(19) 0.0203(9) Uani 1 1 d . . . . .
O2 O 0.5935(2) -0.2711(4) 0.5097(2) 0.0391(12) Uani 1 1 d . . . . .
O3 O 0.5722(2) -0.0606(4) 0.4763(2) 0.0245(9) Uani 1 1 d . . . . .
N1 N 0.4390(2) 0.2458(4) 0.2265(2) 0.0182(10) Uani 1 1 d . . . . .
N2 N 0.6548(2) 0.3718(4) 0.2995(2) 0.0152(10) Uani 1 1 d . . . . .
N3 N 0.5298(2) 0.3686(4) 0.3691(2) 0.0169(10) Uani 1 1 d . . . . .
C1 C 0.5057(3) 0.4830(5) 0.3877(3) 0.0197(12) Uani 1 1 d . . . . .
H1A H 0.513239 0.500432 0.436024 0.024 Uiso 1 1 calc R U . . .
C11 C 0.3838(3) 0.2342(6) 0.2654(3) 0.0220(13) Uani 1 1 d . . . . .
H11A H 0.392780 0.270776 0.310783 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3166(3) 0.1731(6) 0.2428(3) 0.0261(14) Uani 1 1 d . . . . .
H12A H 0.277782 0.173016 0.270147 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3049(3) 0.1086(6) 0.1769(3) 0.0259(14) Uani 1 1 d . . . . .
C14 C 0.2394(3) 0.0318(6) 0.1542(4) 0.0348(17) Uani 1 1 d . . . . .
H14A H 0.200242 0.027224 0.181164 0.042 Uiso 1 1 calc R U . . .
C15 C 0.2324(4) -0.0365(6) 0.0929(4) 0.0362(17) Uani 1 1 d . . . . .
H15A H 0.186822 -0.083745 0.075877 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2915(3) -0.0370(6) 0.0555(3) 0.0338(17) Uani 1 1 d . . . . .
H16A H 0.287553 -0.091494 0.015479 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3550(3) 0.0387(6) 0.0749(3) 0.0320(16) Uani 1 1 d . . . . .
H17A H 0.394058 0.038870 0.047856 0.038 Uiso 1 1 calc R U . . .
C18 C 0.3626(3) 0.1176(5) 0.1359(3) 0.0220(13) Uani 1 1 d . . . . .
C19 C 0.4278(3) 0.1997(5) 0.1605(3) 0.0190(12) Uani 1 1 d . . . . .
C21 C 0.5907(3) 0.1382(5) 0.2879(3) 0.0167(12) Uani 1 1 d . . . . .
C22 C 0.5555(3) 0.0120(5) 0.2846(3) 0.0203(13) Uani 1 1 d . . . . .
H22A H 0.503815 0.005892 0.262603 0.024 Uiso 1 1 calc R U . . .
C23 C 0.5910(3) -0.1015(5) 0.3111(3) 0.0233(13) Uani 1 1 d . . . . .
H23A H 0.564338 -0.183937 0.306715 0.028 Uiso 1 1 calc R U . . .
C24 C 0.6658(3) -0.0968(6) 0.3444(3) 0.0213(13) Uani 1 1 d . . . . .
H24A H 0.690253 -0.174576 0.365305 0.026 Uiso 1 1 calc R U . . .
C25 C 0.7049(3) 0.0239(5) 0.3470(3) 0.0179(12) Uani 1 1 d . . . . .
H25A H 0.756323 0.027823 0.369994 0.022 Uiso 1 1 calc R U . . .
C26 C 0.6700(3) 0.1399(5) 0.3162(3) 0.0158(12) Uani 1 1 d . . . . .
C31 C 0.6777(3) 0.5020(5) 0.3093(3) 0.0194(12) Uani 1 1 d . . . . .
H31A H 0.641346 0.570941 0.296803 0.023 Uiso 1 1 calc R U . . .
C32 C 0.7495(3) 0.5355(5) 0.3359(3) 0.0198(12) Uani 1 1 d . . . . .
H32A H 0.762077 0.626388 0.345812 0.024 Uiso 1 1 calc R U . . .
C33 C 0.8066(3) 0.4367(5) 0.3492(3) 0.0182(12) Uani 1 1 d . . . . .
C34 C 0.8841(3) 0.4691(6) 0.3720(3) 0.0241(13) Uani 1 1 d . . . . .
H34A H 0.898405 0.558472 0.384113 0.029 Uiso 1 1 calc R U . . .
C35 C 0.9384(3) 0.3717(6) 0.3765(3) 0.0247(14) Uani 1 1 d . . . . .
H35A H 0.990270 0.393846 0.392371 0.030 Uiso 1 1 calc R U . . .
C36 C 0.9185(3) 0.2396(6) 0.3579(3) 0.0251(14) Uani 1 1 d . . . . .
H36A H 0.956854 0.173774 0.358487 0.030 Uiso 1 1 calc R U . . .
C37 C 0.8440(3) 0.2064(5) 0.3390(3) 0.0211(13) Uani 1 1 d . . . . .
H37A H 0.831021 0.116251 0.327441 0.025 Uiso 1 1 calc R U . . .
C38 C 0.7852(3) 0.3019(5) 0.3359(3) 0.0167(12) Uani 1 1 d . . . . .
C39 C 0.7061(3) 0.2727(5) 0.3173(3) 0.0137(11) Uani 1 1 d . . . . .
C41 C 0.5547(3) 0.2929(5) 0.1663(3) 0.0180(12) Uani 1 1 d . . . . .
C42 C 0.6143(3) 0.3345(5) 0.1349(3) 0.0232(13) Uani 1 1 d . . . . .
H42A H 0.659532 0.366396 0.163098 0.028 Uiso 1 1 calc R U . . .
C43 C 0.6101(3) 0.3312(6) 0.0640(3) 0.0295(14) Uani 1 1 d . . . . .
H43A H 0.652420 0.358141 0.044136 0.035 Uiso 1 1 calc R U . . .
C44 C 0.5440(3) 0.2886(6) 0.0221(3) 0.0316(15) Uani 1 1 d . . . . .
H44A H 0.539895 0.290813 -0.026746 0.038 Uiso 1 1 calc R U . . .
C45 C 0.4837(4) 0.2427(6) 0.0512(3) 0.0298(15) Uani 1 1 d . . . . .
H45A H 0.438763 0.211939 0.022162 0.036 Uiso 1 1 calc R U . . .
C46 C 0.4884(3) 0.2414(5) 0.1230(3) 0.0212(13) Uani 1 1 d . . . . .
C51 C 0.4650(3) 0.5915(5) 0.2708(3) 0.0176(12) Uani 1 1 d . . . . .
C52 C 0.4217(3) 0.6969(5) 0.2336(3) 0.0233(13) Uani 1 1 d . . . . .
H52A H 0.415010 0.699315 0.184591 0.028 Uiso 1 1 calc R U . . .
C53 C 0.3900(3) 0.7940(6) 0.2681(4) 0.0300(15) Uani 1 1 d . . . . .
H53A H 0.361953 0.863734 0.242484 0.036 Uiso 1 1 calc R U . . .
C54 C 0.3975(3) 0.7935(6) 0.3389(3) 0.0274(14) Uani 1 1 d . . . . .
H54A H 0.375373 0.862610 0.361851 0.033 Uiso 1 1 calc R U . . .
C55 C 0.4371(3) 0.6924(6) 0.3763(3) 0.0245(13) Uani 1 1 d . . . . .
H55A H 0.443422 0.693330 0.425387 0.029 Uiso 1 1 calc R U . . .
C56 C 0.4687(3) 0.5866(5) 0.3427(3) 0.0158(12) Uani 1 1 d . . . . .
C61 C 0.5729(3) 0.2854(5) 0.4218(3) 0.0181(12) Uani 1 1 d . . . . .
C62 C 0.6419(3) 0.3291(6) 0.4591(3) 0.0239(13) Uani 1 1 d . . . . .
H62A H 0.657102 0.419139 0.455183 0.029 Uiso 1 1 calc R U . . .
C63 C 0.6887(3) 0.2417(6) 0.5020(3) 0.0213(13) Uani 1 1 d . . . . .
H63A H 0.735430 0.273316 0.527692 0.026 Uiso 1 1 calc R U . . .
C64 C 0.6684(3) 0.1086(5) 0.5082(3) 0.0196(12) Uani 1 1 d . . . . .
C65 C 0.7167(3) 0.0102(6) 0.5485(3) 0.0269(14) Uani 1 1 d . . . . .
C66 C 0.6908(3) -0.1151(6) 0.5492(3) 0.0286(15) Uani 1 1 d . . . . .
H66A H 0.722245 -0.179091 0.576190 0.034 Uiso 1 1 calc R U . . .
C67 C 0.6182(3) -0.1592(6) 0.5114(3) 0.0308(15) Uani 1 1 d . . . . .
C68 C 0.5979(3) 0.0689(5) 0.4722(3) 0.0209(13) Uani 1 1 d . . . . .
C69 C 0.5501(3) 0.1525(5) 0.4292(3) 0.0196(12) Uani 1 1 d . . . . .
H69A H 0.502567 0.121289 0.404987 0.024 Uiso 1 1 calc R U . . .
C70 C 0.7934(3) 0.0500(7) 0.5885(4) 0.046(2) Uani 1 1 d . . . . .
H70A H 0.818345 -0.028236 0.612516 0.069 Uiso 1 1 calc R U . . .
H70B H 0.786828 0.118600 0.622528 0.069 Uiso 1 1 calc R U . . .
H70C H 0.824798 0.085385 0.556615 0.069 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 C21 1.996(5) . ?
Ir1 C41 1.997(6) . ?
Ir1 N2 2.034(4) . ?
Ir1 N1 2.041(4) . ?
Ir1 O1 2.126(3) . ?
Ir1 N3 2.169(5) . ?
O1 C51 1.315(6) . ?
O2 C67 1.203(7) . ?
O3 C68 1.384(6) . ?
O3 C67 1.388(6) . ?
N1 C11 1.358(7) . ?
N1 C19 1.358(7) . ?
N2 C39 1.354(6) . ?
N2 C31 1.372(6) . ?
N3 C1 1.300(6) . ?
N3 C61 1.441(7) . ?
C1 C56 1.445(7) . ?
C11 C12 1.351(7) . ?
C12 C13 1.427(8) . ?
C13 C14 1.406(8) . ?
C13 C18 1.420(8) . ?
C14 C15 1.372(9) . ?
C15 C16 1.390(9) . ?
C16 C17 1.362(8) . ?
C17 C18 1.421(8) . ?
C18 C19 1.438(7) . ?
C19 C46 1.475(8) . ?
C21 C22 1.409(7) . ?
C21 C26 1.426(7) . ?
C22 C23 1.360(7) . ?
C23 C24 1.381(7) . ?
C24 C25 1.393(7) . ?
C25 C26 1.405(7) . ?
C26 C39 1.477(7) . ?
C31 C32 1.338(7) . ?
C32 C33 1.413(7) . ?
C33 C34 1.415(7) . ?
C33 C38 1.416(7) . ?
C34 C35 1.369(8) . ?
C35 C36 1.402(8) . ?
C36 C37 1.358(7) . ?
C37 C38 1.416(7) . ?
C38 C39 1.426(7) . ?
C41 C42 1.386(8) . ?
C41 C46 1.427(7) . ?
C42 C43 1.382(8) . ?
C43 C44 1.381(8) . ?
C44 C45 1.386(8) . ?
C45 C46 1.397(8) . ?
C51 C56 1.404(7) . ?
C51 C52 1.430(7) . ?
C52 C53 1.366(8) . ?
C53 C54 1.373(9) . ?
C54 C55 1.372(8) . ?
C55 C56 1.419(7) . ?
C61 C62 1.388(7) . ?
C61 C69 1.407(7) . ?
C62 C63 1.388(7) . ?
C63 C64 1.393(7) . ?
C64 C68 1.389(7) . ?
C64 C65 1.450(7) . ?
C65 C66 1.339(8) . ?
C65 C70 1.506(8) . ?
C66 C67 1.445(8) . ?
C68 C69 1.374(7) . ?

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
C21 Ir1 C41 90.1(2) . . ?
C21 Ir1 N2 80.28(19) . . ?
C41 Ir1 N2 96.21(19) . . ?
C21 Ir1 N1 94.65(19) . . ?
C41 Ir1 N1 80.3(2) . . ?
N2 Ir1 N1 173.87(17) . . ?
C21 Ir1 O1 175.80(19) . . ?
C41 Ir1 O1 86.24(17) . . ?
N2 Ir1 O1 98.10(15) . . ?
N1 Ir1 O1 86.73(15) . . ?
C21 Ir1 N3 96.61(19) . . ?
C41 Ir1 N3 173.28(18) . . ?
N2 Ir1 N3 84.27(17) . . ?
N1 Ir1 N3 99.82(17) . . ?
O1 Ir1 N3 87.05(15) . . ?
C51 O1 Ir1 127.1(3) . . ?
C68 O3 C67 121.5(4) . . ?
C11 N1 C19 120.7(5) . . ?
C11 N1 Ir1 122.7(4) . . ?
C19 N1 Ir1 116.4(4) . . ?
C39 N2 C31 119.4(4) . . ?
C39 N2 Ir1 117.4(3) . . ?
C31 N2 Ir1 123.1(3) . . ?
C1 N3 C61 118.0(5) . . ?
C1 N3 Ir1 125.1(4) . . ?
C61 N3 Ir1 113.6(3) . . ?
N3 C1 C56 126.9(5) . . ?
C12 C11 N1 123.1(6) . . ?
C11 C12 C13 118.8(6) . . ?
C14 C13 C18 120.2(6) . . ?
C14 C13 C12 120.9(6) . . ?
C18 C13 C12 118.8(5) . . ?
C15 C14 C13 119.5(7) . . ?
C14 C15 C16 120.5(6) . . ?
C17 C16 C15 121.6(6) . . ?
C16 C17 C18 119.7(6) . . ?
C13 C18 C17 118.3(5) . . ?
C13 C18 C19 118.2(5) . . ?
C17 C18 C19 123.4(6) . . ?
N1 C19 C18 119.2(5) . . ?
N1 C19 C46 112.6(5) . . ?
C18 C19 C46 128.2(5) . . ?
C22 C21 C26 115.7(5) . . ?
C22 C21 Ir1 129.6(4) . . ?
C26 C21 Ir1 114.6(4) . . ?
C23 C22 C21 124.0(5) . . ?
C22 C23 C24 119.9(5) . . ?
C23 C24 C25 118.9(5) . . ?
C24 C25 C26 121.4(5) . . ?
C25 C26 C21 119.5(5) . . ?
C25 C26 C39 125.4(5) . . ?
C21 C26 C39 114.7(5) . . ?
C32 C31 N2 122.3(5) . . ?
C31 C32 C33 120.5(5) . . ?
C32 C33 C34 122.1(5) . . ?
C32 C33 C38 118.1(5) . . ?
C34 C33 C38 119.7(5) . . ?
C35 C34 C33 120.0(5) . . ?
C34 C35 C36 120.8(5) . . ?
C37 C36 C35 119.6(5) . . ?
C36 C37 C38 122.0(5) . . ?
C33 C38 C37 117.5(5) . . ?
C33 C38 C39 117.8(5) . . ?
C37 C38 C39 124.5(5) . . ?
N2 C39 C38 120.6(5) . . ?
N2 C39 C26 112.5(4) . . ?
C38 C39 C26 126.8(5) . . ?
C42 C41 C46 117.8(5) . . ?
C42 C41 Ir1 127.1(4) . . ?
C46 C41 Ir1 114.7(4) . . ?
C43 C42 C41 122.2(5) . . ?
C44 C43 C42 119.7(6) . . ?
C43 C44 C45 120.2(6) . . ?
C44 C45 C46 120.5(5) . . ?
C45 C46 C41 119.5(5) . . ?
C45 C46 C19 126.1(5) . . ?
C41 C46 C19 114.3(5) . . ?
O1 C51 C56 125.3(5) . . ?
O1 C51 C52 117.0(5) . . ?
C56 C51 C52 117.6(5) . . ?
C53 C52 C51 120.5(6) . . ?
C52 C53 C54 121.7(6) . . ?
C55 C54 C53 119.6(6) . . ?
C54 C55 C56 120.9(6) . . ?
C51 C56 C55 119.4(5) . . ?
C51 C56 C1 125.1(5) . . ?
C55 C56 C1 115.4(5) . . ?
C62 C61 C69 119.4(5) . . ?
C62 C61 N3 120.5(5) . . ?
C69 C61 N3 119.6(5) . . ?
C63 C62 C61 120.3(5) . . ?
C62 C63 C64 121.3(5) . . ?
C68 C64 C63 117.1(5) . . ?
C68 C64 C65 118.8(5) . . ?
C63 C64 C65 124.1(5) . . ?
C66 C65 C64 118.0(5) . . ?
C66 C65 C70 121.8(5) . . ?
C64 C65 C70 120.2(5) . . ?
C65 C66 C67 124.3(5) . . ?
O2 C67 O3 117.9(5) . . ?
O2 C67 C66 126.2(6) . . ?
O3 C67 C66 115.8(5) . . ?
C69 C68 O3 115.5(5) . . ?
C69 C68 C64 123.1(5) . . ?
O3 C68 C64 121.3(5) . . ?
C68 C69 C61 118.8(5) . . ?

_refine_diff_density_max         2.001
_refine_diff_density_min         -1.207
_refine_diff_density_rms         0.163



