# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1528504'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;
_audit_creation_date             2016-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H30 Ir N6, Cl'
_chemical_formula_sum            'C42 H30 Cl Ir N6'
_chemical_formula_weight         846.37
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.3299(5)
_cell_length_b                   13.6244(4)
_cell_length_c                   15.0507(5)
_cell_angle_alpha                99.8240(10)
_cell_angle_beta                 101.6270(10)
_cell_angle_gamma                115.7660(10)
_cell_volume                     2305.48(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9242
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.04
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.984
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.276
_exptl_transmission_factor_max   0.362
_exptl_transmission_factor_min   0.362
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22627
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.403
_diffrn_reflns_theta_min         3.036
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9242
_reflns_number_total             10409
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         4.386
_refine_diff_density_min         -3.610
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         10409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0745P)²+3.4755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1388
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C28(H28), C27(H27), C29(H29), C26(H26), C11(H11), C14(H14), C12(H12), C2(H2),
 C17(H17), C20(H20), C13(H13), C18(H18), C3(H3), C19(H19), C5(H5), C4(H4),
 C31(H31), C32(H32), C33(H33), C40(H40), C41(H41), C42(H42), C39(H39), C38(H38)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.63107(2) 0.84610(2) 0.74502(2) 0.01957(8) Uani 1 1 d . . . . .
C10 C 0.7916(5) 0.7823(4) 0.6827(4) 0.0259(12) Uani 1 1 d . . . . .
N1 N 0.5958(4) 0.7368(4) 0.6153(3) 0.0194(9) Uani 1 1 d . . . . .
N3 N 0.6698(4) 0.9392(4) 0.8830(3) 0.0224(9) Uani 1 1 d . . . . .
N4 N 0.6622(5) 1.0535(4) 1.0542(3) 0.0278(10) Uani 1 1 d . . . . .
N2 N 0.5819(5) 0.6315(4) 0.4332(3) 0.0277(10) Uani 1 1 d . . . . .
C30 C 0.5579(5) 0.7222(4) 0.8030(4) 0.0196(10) Uani 1 1 d . . . . .
C28 C 0.4613(5) 0.5242(5) 0.8052(4) 0.0279(12) Uani 1 1 d . . . . .
H28 H 0.4298 0.4470 0.7747 0.034 Uiso 1 1 calc R . . . .
C27 C 0.4593(6) 0.5592(5) 0.8971(4) 0.0305(13) Uani 1 1 d . . . . .
H27 H 0.4274 0.5054 0.9283 0.037 Uiso 1 1 calc R . . . .
C29 C 0.5105(5) 0.6045(5) 0.7595(4) 0.0244(11) Uani 1 1 d . . . . .
H29 H 0.5123 0.5803 0.6985 0.029 Uiso 1 1 calc R . . . .
C26 C 0.5050(5) 0.6747(5) 0.9422(4) 0.0272(12) Uani 1 1 d . . . . .
H26 H 0.5052 0.6983 1.0040 0.033 Uiso 1 1 calc R . . . .
C25 C 0.5510(5) 0.7557(4) 0.8941(4) 0.0231(11) Uani 1 1 d . . . . .
C7 C 0.6833(5) 0.6869(4) 0.5013(4) 0.0263(12) Uani 1 1 d . . . . .
C24 C 0.6086(5) 0.8797(4) 0.9341(4) 0.0213(10) Uani 1 1 d . . . . .
C1 C 0.4887(5) 0.6712(4) 0.5472(4) 0.0210(11) Uani 1 1 d . . . . .
C23 C 0.5152(5) 0.8826(5) 1.0711(4) 0.0288(12) Uani 1 1 d . . . . .
H23A H 0.5493 0.8524 1.1138 0.043 Uiso 1 1 calc GR . . . .
H23B H 0.4436 0.8216 1.0259 0.043 Uiso 1 1 calc GR . . . .
H23C H 0.4992 0.9367 1.1065 0.043 Uiso 1 1 calc GR . . . .
C21 C 0.7400(5) 1.1107(5) 1.0109(4) 0.0264(12) Uani 1 1 d . . . . .
C16 C 0.7448(5) 1.0552(4) 0.9234(4) 0.0250(11) Uani 1 1 d . . . . .
C9 C 0.6913(5) 0.7358(4) 0.5988(4) 0.0235(11) Uani 1 1 d . . . . .
C11 C 0.8947(5) 0.7750(5) 0.6890(4) 0.0323(13) Uani 1 1 d . . . . .
H11 H 0.9060 0.7434 0.6346 0.039 Uiso 1 1 calc R . . . .
C22 C 0.6000(5) 0.9410(5) 1.0196(4) 0.0250(11) Uani 1 1 d . . . . .
C15 C 0.7749(5) 0.8314(5) 0.7656(4) 0.0251(11) Uani 1 1 d . . . . .
C14 C 0.8637(5) 0.8700(5) 0.8538(4) 0.0279(12) Uani 1 1 d . . . . .
H14 H 0.8541 0.9012 0.9093 0.033 Uiso 1 1 calc R . . . .
C6 C 0.4824(5) 0.6161(5) 0.4553(4) 0.0253(11) Uani 1 1 d . . . . .
C12 C 0.9795(6) 0.8148(6) 0.7763(5) 0.0396(15) Uani 1 1 d . . . . .
H12 H 1.0476 0.8099 0.7799 0.047 Uiso 1 1 calc R . . . .
N5 N 0.4896(4) 0.8895(4) 0.7176(3) 0.0229(9) Uani 1 1 d . . . . .
N6 N 0.6904(5) 0.9770(4) 0.6722(3) 0.0301(11) Uani 1 1 d . . . . .
C2 C 0.3829(5) 0.6514(4) 0.5665(4) 0.0248(11) Uani 1 1 d . . . . .
H2 H 0.3848 0.6843 0.6267 0.030 Uiso 1 1 calc R . . . .
C17 C 0.8302(6) 1.1186(5) 0.8836(4) 0.0323(13) Uani 1 1 d . . . . .
H17 H 0.8368 1.0822 0.8287 0.039 Uiso 1 1 calc R . . . .
C20 C 0.8135(6) 1.2305(5) 1.0515(4) 0.0335(13) Uani 1 1 d . . . . .
H20 H 0.8071 1.2687 1.1057 0.040 Uiso 1 1 calc R . . . .
C13 C 0.9641(6) 0.8615(6) 0.8578(5) 0.0375(14) Uani 1 1 d . . . . .
H13 H 1.0216 0.8875 0.9159 0.045 Uiso 1 1 calc R . . . .
C18 C 0.9038(6) 1.2341(5) 0.9257(5) 0.0396(15) Uani 1 1 d . . . . .
H18 H 0.9594 1.2752 0.8987 0.048 Uiso 1 1 calc R . . . .
C3 C 0.2775(6) 0.5836(5) 0.4961(4) 0.0344(14) Uani 1 1 d . . . . .
H3 H 0.2084 0.5720 0.5088 0.041 Uiso 1 1 calc R . . . .
C35 C 0.5097(6) 0.9750(5) 0.6761(4) 0.0291(13) Uani 1 1 d . . . . .
C19 C 0.8950(6) 1.2897(5) 1.0091(5) 0.0378(15) Uani 1 1 d . . . . .
H19 H 0.9448 1.3676 1.0365 0.045 Uiso 1 1 calc R . . . .
C5 C 0.3739(6) 0.5477(6) 0.3847(4) 0.0351(14) Uani 1 1 d . . . . .
H5 H 0.3708 0.5136 0.3244 0.042 Uiso 1 1 calc R . . . .
C36 C 0.6177(6) 1.0213(5) 0.6520(4) 0.0312(13) Uani 1 1 d . . . . .
C4 C 0.2724(6) 0.5305(6) 0.4036(5) 0.0407(16) Uani 1 1 d . . . . .
H4 H 0.2005 0.4846 0.3566 0.049 Uiso 1 1 calc R . . . .
C31 C 0.3905(5) 0.8466(5) 0.7406(4) 0.0282(12) Uani 1 1 d . . . . .
H31 H 0.3775 0.7917 0.7726 0.034 Uiso 1 1 calc R . . . .
C32 C 0.3064(6) 0.8799(6) 0.7192(4) 0.0336(14) Uani 1 1 d . . . . .
H32 H 0.2380 0.8461 0.7353 0.040 Uiso 1 1 calc R . . . .
C33 C 0.3238(7) 0.9626(6) 0.6742(4) 0.0391(16) Uani 1 1 d . . . . .
H33 H 0.2663 0.9833 0.6572 0.047 Uiso 1 1 calc R . . . .
C34 C 0.4297(6) 1.0154(5) 0.6545(4) 0.0359(15) Uani 1 1 d . . . . .
C40 C 0.7857(6) 1.0136(5) 0.6430(5) 0.0381(16) Uani 1 1 d . . . . .
H40 H 0.8352 0.9827 0.6550 0.046 Uiso 1 1 calc R . . . .
C8 C 0.7885(6) 0.7025(6) 0.4704(5) 0.0428(17) Uani 1 1 d . . . . .
H8A H 0.8179 0.6555 0.4934 0.064 Uiso 1 1 calc GR . . . .
H8B H 0.8484 0.7810 0.4957 0.064 Uiso 1 1 calc GR . . . .
H8C H 0.7664 0.6809 0.4024 0.064 Uiso 1 1 calc GR . . . .
C41 C 0.4595(8) 1.1064(6) 0.6112(5) 0.0470(19) Uani 1 1 d . . . . .
H41 H 0.4086 1.1357 0.5988 0.056 Uiso 1 1 calc R . . . .
C37 C 0.6417(7) 1.1082(5) 0.6054(5) 0.0460(19) Uani 1 1 d . . . . .
C42 C 0.5586(8) 1.1498(6) 0.5883(5) 0.054(2) Uani 1 1 d . . . . .
H42 H 0.5747 1.2086 0.5604 0.065 Uiso 1 1 calc R . . . .
C39 C 0.8131(8) 1.0973(6) 0.5946(5) 0.051(2) Uani 1 1 d . . . . .
H39 H 0.8788 1.1192 0.5741 0.061 Uiso 1 1 calc R . . . .
C38 C 0.7454(8) 1.1449(5) 0.5782(5) 0.051(2) Uani 1 1 d . . . . .
H38 H 0.7659 1.2024 0.5489 0.061 Uiso 1 1 calc R . . . .
Cl1 Cl 1.0589(3) 0.9805(3) 0.5715(3) 0.1329(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N1 2.068(4) . ?
Ir1 N3 2.071(4) . ?
Ir1 C30 1.993(5) . ?
Ir1 C15 1.983(6) . ?
Ir1 N5 2.194(5) . ?
Ir1 N6 2.190(5) . ?
C10 C9 1.447(8) . ?
C10 C11 1.406(8) . ?
C10 C15 1.418(7) . ?
N1 C1 1.370(7) . ?
N1 C9 1.351(7) . ?
N3 C24 1.344(7) . ?
N3 C16 1.386(7) . ?
N4 C21 1.360(8) . ?
N4 C22 1.325(8) . ?
N2 C7 1.318(8) . ?
N2 C6 1.369(8) . ?
C30 C29 1.412(7) . ?
C30 C25 1.404(7) . ?
C28 H28 0.9300 . ?
C28 C27 1.393(9) . ?
C28 C29 1.385(8) . ?
C27 H27 0.9300 . ?
C27 C26 1.395(8) . ?
C29 H29 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.407(8) . ?
C25 C24 1.464(7) . ?
C7 C9 1.466(7) . ?
C7 C8 1.506(8) . ?
C24 C22 1.464(7) . ?
C1 C6 1.425(7) . ?
C1 C2 1.416(8) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 C22 1.515(8) . ?
C21 C16 1.430(7) . ?
C21 C20 1.424(8) . ?
C16 C17 1.413(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(9) . ?
C15 C14 1.423(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(8) . ?
C6 C5 1.400(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(9) . ?
N5 C35 1.366(7) . ?
N5 C31 1.337(8) . ?
N6 C36 1.358(8) . ?
N6 C40 1.344(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(8) . ?
C20 H20 0.9300 . ?
C20 C19 1.390(9) . ?
C13 H13 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.406(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.429(9) . ?
C35 C36 1.450(9) . ?
C35 C34 1.406(9) . ?
C19 H19 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.367(9) . ?
C36 C37 1.428(8) . ?
C4 H4 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.384(8) . ?
C32 H32 0.9300 . ?
C32 C33 1.370(10) . ?
C33 H33 0.9300 . ?
C33 C34 1.399(11) . ?
C34 C41 1.440(9) . ?
C40 H40 0.9300 . ?
C40 C39 1.412(9) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C41 H41 0.9300 . ?
C41 C42 1.337(12) . ?
C37 C42 1.447(12) . ?
C37 C38 1.423(12) . ?
C42 H42 0.9300 . ?
C39 H39 0.9300 . ?
C39 C38 1.330(12) . ?
C38 H38 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
N1 Ir1 N3 172.05(16) . . ?
N1 Ir1 N5 102.42(17) . . ?
N1 Ir1 N6 83.53(17) . . ?
N3 Ir1 N5 83.22(17) . . ?
N3 Ir1 N6 103.42(17) . . ?
C30 Ir1 N1 94.86(19) . . ?
C30 Ir1 N3 78.7(2) . . ?
C30 Ir1 N5 97.98(19) . . ?
C30 Ir1 N6 173.2(2) . . ?
C15 Ir1 N1 78.9(2) . . ?
C15 Ir1 N3 96.5(2) . . ?
C15 Ir1 C30 91.4(2) . . ?
C15 Ir1 N5 170.3(2) . . ?
C15 Ir1 N6 94.7(2) . . ?
N6 Ir1 N5 76.02(19) . . ?
C11 C10 C9 126.5(5) . . ?
C11 C10 C15 119.9(5) . . ?
C15 C10 C9 113.4(5) . . ?
C1 N1 Ir1 126.4(4) . . ?
C9 N1 Ir1 114.1(4) . . ?
C9 N1 C1 119.5(4) . . ?
C24 N3 Ir1 114.7(3) . . ?
C24 N3 C16 118.7(5) . . ?
C16 N3 Ir1 126.5(4) . . ?
C22 N4 C21 117.9(5) . . ?
C7 N2 C6 119.0(5) . . ?
C29 C30 Ir1 125.6(4) . . ?
C25 C30 Ir1 116.7(4) . . ?
C25 C30 C29 117.7(5) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C29 C28 C27 119.8(5) . . ?
C28 C27 H27 120.0 . . ?
C28 C27 C26 120.0(5) . . ?
C26 C27 H27 120.0 . . ?
C30 C29 H29 119.1 . . ?
C28 C29 C30 121.7(5) . . ?
C28 C29 H29 119.1 . . ?
C27 C26 H26 120.0 . . ?
C27 C26 C25 119.9(5) . . ?
C25 C26 H26 120.0 . . ?
C30 C25 C26 120.7(5) . . ?
C30 C25 C24 112.8(5) . . ?
C26 C25 C24 126.0(5) . . ?
N2 C7 C9 121.1(5) . . ?
N2 C7 C8 115.5(5) . . ?
C9 C7 C8 123.3(5) . . ?
N3 C24 C25 114.7(5) . . ?
N3 C24 C22 119.2(5) . . ?
C22 C24 C25 126.0(5) . . ?
N1 C1 C6 119.2(5) . . ?
N1 C1 C2 122.1(5) . . ?
C2 C1 C6 118.6(5) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
N4 C21 C16 121.9(5) . . ?
N4 C21 C20 118.5(5) . . ?
C20 C21 C16 119.5(6) . . ?
N3 C16 C21 118.9(5) . . ?
N3 C16 C17 121.8(5) . . ?
C17 C16 C21 119.2(5) . . ?
C10 C9 C7 127.0(5) . . ?
N1 C9 C10 114.4(5) . . ?
N1 C9 C7 118.5(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(6) . . ?
C12 C11 H11 120.0 . . ?
N4 C22 C24 121.6(5) . . ?
N4 C22 C23 115.3(5) . . ?
C24 C22 C23 123.0(5) . . ?
C10 C15 Ir1 115.6(4) . . ?
C10 C15 C14 118.1(5) . . ?
C14 C15 Ir1 126.3(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 C15 120.7(5) . . ?
C13 C14 H14 119.6 . . ?
N2 C6 C1 121.0(5) . . ?
N2 C6 C5 118.7(5) . . ?
C5 C6 C1 120.3(5) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(6) . . ?
C13 C12 H12 119.6 . . ?
C35 N5 Ir1 114.8(4) . . ?
C31 N5 Ir1 128.1(4) . . ?
C31 N5 C35 117.0(5) . . ?
C36 N6 Ir1 114.4(4) . . ?
C40 N6 Ir1 127.6(5) . . ?
C40 N6 C36 118.0(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(5) . . ?
C3 C2 H2 120.0 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(6) . . ?
C18 C17 H17 119.7 . . ?
C21 C20 H20 120.4 . . ?
C19 C20 C21 119.1(6) . . ?
C19 C20 H20 120.4 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.4(6) . . ?
C12 C13 H13 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.1(6) . . ?
C19 C18 H18 119.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
N5 C35 C36 116.5(5) . . ?
N5 C35 C34 122.8(6) . . ?
C34 C35 C36 120.6(5) . . ?
C20 C19 C18 121.3(6) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
N6 C36 C35 118.1(5) . . ?
N6 C36 C37 122.7(6) . . ?
C37 C36 C35 119.1(6) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(6) . . ?
C5 C4 H4 120.2 . . ?
N5 C31 H31 118.4 . . ?
N5 C31 C32 123.2(6) . . ?
C32 C31 H31 118.4 . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.1(7) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 120.7 . . ?
C32 C33 C34 118.6(6) . . ?
C34 C33 H33 120.7 . . ?
C35 C34 C41 118.5(7) . . ?
C33 C34 C35 118.0(6) . . ?
C33 C34 C41 123.5(6) . . ?
N6 C40 H40 118.9 . . ?
N6 C40 C39 122.2(7) . . ?
C39 C40 H40 118.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C34 C41 H41 119.2 . . ?
C42 C41 C34 121.6(7) . . ?
C42 C41 H41 119.2 . . ?
C36 C37 C42 118.0(7) . . ?
C38 C37 C36 116.4(7) . . ?
C38 C37 C42 125.6(6) . . ?
C41 C42 C37 122.1(6) . . ?
C41 C42 H42 118.9 . . ?
C37 C42 H42 118.9 . . ?
C40 C39 H39 119.8 . . ?
C38 C39 C40 120.3(8) . . ?
C38 C39 H39 119.8 . . ?
C37 C38 H38 119.8 . . ?
C39 C38 C37 120.3(6) . . ?
C39 C38 H38 119.8 . . ?

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 N1 C1 C6 168.9(4) . . . . ?
Ir1 N1 C1 C2 -14.4(7) . . . . ?
Ir1 N1 C9 C10 17.8(6) . . . . ?
Ir1 N1 C9 C7 -163.7(4) . . . . ?
Ir1 N3 C24 C25 16.3(6) . . . . ?
Ir1 N3 C24 C22 -160.7(4) . . . . ?
Ir1 N3 C16 C21 164.8(4) . . . . ?
Ir1 N3 C16 C17 -19.0(8) . . . . ?
Ir1 C30 C29 C28 179.9(4) . . . . ?
Ir1 C30 C25 C26 -177.4(4) . . . . ?
Ir1 C30 C25 C24 -4.6(6) . . . . ?
Ir1 C15 C14 C13 -175.6(5) . . . . ?
Ir1 N5 C35 C36 2.9(6) . . . . ?
Ir1 N5 C35 C34 -179.1(4) . . . . ?
Ir1 N5 C31 C32 -179.6(4) . . . . ?
Ir1 N6 C36 C35 -2.6(6) . . . . ?
Ir1 N6 C36 C37 179.5(4) . . . . ?
Ir1 N6 C40 C39 178.5(5) . . . . ?
C10 C11 C12 C13 0.3(10) . . . . ?
C10 C15 C14 C13 1.1(9) . . . . ?
N1 C1 C6 N2 -2.6(8) . . . . ?
N1 C1 C6 C5 179.4(5) . . . . ?
N1 C1 C2 C3 -179.1(5) . . . . ?
N3 C24 C22 N4 -8.3(8) . . . . ?
N3 C24 C22 C23 168.0(5) . . . . ?
N3 C16 C17 C18 -179.8(6) . . . . ?
N4 C21 C16 N3 -1.6(9) . . . . ?
N4 C21 C16 C17 -177.9(6) . . . . ?
N4 C21 C20 C19 178.7(6) . . . . ?
N2 C7 C9 C10 169.4(5) . . . . ?
N2 C7 C9 N1 -9.0(8) . . . . ?
N2 C6 C5 C4 -179.7(6) . . . . ?
C30 C25 C24 N3 -7.9(7) . . . . ?
C30 C25 C24 C22 168.9(5) . . . . ?
C28 C27 C26 C25 1.4(9) . . . . ?
C27 C28 C29 C30 -0.8(9) . . . . ?
C27 C26 C25 C30 -3.9(9) . . . . ?
C27 C26 C25 C24 -175.7(5) . . . . ?
C29 C30 C25 C26 4.0(8) . . . . ?
C29 C30 C25 C24 176.8(5) . . . . ?
C29 C28 C27 C26 1.0(9) . . . . ?
C26 C25 C24 N3 164.5(5) . . . . ?
C26 C25 C24 C22 -18.8(9) . . . . ?
C25 C30 C29 C28 -1.6(8) . . . . ?
C25 C24 C22 N4 175.1(5) . . . . ?
C25 C24 C22 C23 -8.7(8) . . . . ?
C7 N2 C6 C1 8.2(8) . . . . ?
C7 N2 C6 C5 -173.8(6) . . . . ?
C24 N3 C16 C21 -10.3(8) . . . . ?
C24 N3 C16 C17 165.9(6) . . . . ?
C1 N1 C9 C10 -164.1(5) . . . . ?
C1 N1 C9 C7 14.5(7) . . . . ?
C1 C6 C5 C4 -1.7(9) . . . . ?
C1 C2 C3 C4 1.2(9) . . . . ?
C21 N4 C22 C24 -3.5(8) . . . . ?
C21 N4 C22 C23 179.9(5) . . . . ?
C21 C16 C17 C18 -3.7(10) . . . . ?
C21 C20 C19 C18 1.8(10) . . . . ?
C16 N3 C24 C25 -168.1(5) . . . . ?
C16 N3 C24 C22 14.9(7) . . . . ?
C16 C21 C20 C19 -5.0(9) . . . . ?
C16 C17 C18 C19 0.5(11) . . . . ?
C9 C10 C11 C12 -174.2(6) . . . . ?
C9 C10 C15 Ir1 -8.7(6) . . . . ?
C9 C10 C15 C14 174.2(5) . . . . ?
C9 N1 C1 C6 -9.0(7) . . . . ?
C9 N1 C1 C2 167.7(5) . . . . ?
C11 C10 C9 N1 168.8(6) . . . . ?
C11 C10 C9 C7 -9.6(9) . . . . ?
C11 C10 C15 Ir1 175.8(4) . . . . ?
C11 C10 C15 C14 -1.2(8) . . . . ?
C11 C12 C13 C14 -0.3(11) . . . . ?
C22 N4 C21 C16 8.3(8) . . . . ?
C22 N4 C21 C20 -175.4(5) . . . . ?
C15 C10 C9 N1 -6.3(7) . . . . ?
C15 C10 C9 C7 175.3(5) . . . . ?
C15 C10 C11 C12 0.5(9) . . . . ?
C15 C14 C13 C12 -0.4(10) . . . . ?
C6 N2 C7 C9 -2.5(8) . . . . ?
C6 N2 C7 C8 -178.6(5) . . . . ?
C6 C1 C2 C3 -2.4(8) . . . . ?
C6 C5 C4 C3 0.4(10) . . . . ?
N5 C35 C36 N6 -0.2(8) . . . . ?
N5 C35 C36 C37 177.8(5) . . . . ?
N5 C35 C34 C33 -1.9(8) . . . . ?
N5 C35 C34 C41 179.7(5) . . . . ?
N5 C31 C32 C33 -1.6(9) . . . . ?
N6 C36 C37 C42 -179.4(5) . . . . ?
N6 C36 C37 C38 1.7(9) . . . . ?
N6 C40 C39 C38 1.5(10) . . . . ?
C2 C1 C6 N2 -179.4(5) . . . . ?
C2 C1 C6 C5 2.6(8) . . . . ?
C2 C3 C4 C5 -0.2(10) . . . . ?
C17 C18 C19 C20 0.4(11) . . . . ?
C20 C21 C16 N3 -177.8(5) . . . . ?
C20 C21 C16 C17 5.9(9) . . . . ?
C35 N5 C31 C32 4.1(8) . . . . ?
C35 C36 C37 C42 2.7(8) . . . . ?
C35 C36 C37 C38 -176.2(5) . . . . ?
C35 C34 C41 C42 2.5(10) . . . . ?
C36 N6 C40 C39 1.5(9) . . . . ?
C36 C35 C34 C33 176.1(5) . . . . ?
C36 C35 C34 C41 -2.3(8) . . . . ?
C36 C37 C42 C41 -2.7(10) . . . . ?
C36 C37 C38 C39 1.4(10) . . . . ?
C31 N5 C35 C36 179.7(5) . . . . ?
C31 N5 C35 C34 -2.3(8) . . . . ?
C31 C32 C33 C34 -2.7(9) . . . . ?
C32 C33 C34 C35 4.3(9) . . . . ?
C32 C33 C34 C41 -177.4(6) . . . . ?
C33 C34 C41 C42 -175.9(6) . . . . ?
C34 C35 C36 N6 -178.3(5) . . . . ?
C34 C35 C36 C37 -0.3(8) . . . . ?
C34 C41 C42 C37 0.1(11) . . . . ?
C40 N6 C36 C35 174.8(5) . . . . ?
C40 N6 C36 C37 -3.1(8) . . . . ?
C40 C39 C38 C37 -2.9(11) . . . . ?
C8 C7 C9 C10 -14.9(9) . . . . ?
C8 C7 C9 N1 166.8(5) . . . . ?
C42 C37 C38 C39 -177.4(7) . . . . ?
C38 C37 C42 C41 176.1(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
