# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1550506'
_audit_update_record             
;
2017-05-16 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H26 F4 Ir N6, F6 P'
_chemical_formula_sum            'C41 H26 F10 Ir N6 P'
_chemical_formula_weight         1015.85

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.1303(6)
_cell_length_b                   13.8487(8)
_cell_length_c                   14.4314(9)
_cell_angle_alpha                84.7650(10)
_cell_angle_beta                 78.8280(10)
_cell_angle_gamma                70.7100(10)
_cell_volume                     1873.92(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3217
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      22.20

_exptl_crystal_description       blocky
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    3.696
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.455
_exptl_absorpt_correction_T_max  0.574
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruke Smart Aepex CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10534
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.439
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             6517
_reflns_number_gt                5677
_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, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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     
'w=1/[σ²(Fo²)+(0.0253P)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         6517
_refine_ls_number_parameters     532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.82119(2) 0.15342(2) 0.30345(2) 0.02769(7) Uani 1 1 d . . . . .
P1 P 0.07157(18) 0.66427(13) 0.12480(13) 0.0556(4) Uani 1 1 d . . . . .
F6 F 0.0239(4) 0.5810(3) 0.0812(3) 0.0814(12) Uani 1 1 d . . . . .
F10 F 0.2215(5) 0.6212(4) 0.0607(4) 0.1179(18) Uani 1 1 d . . . . .
F8 F 0.0222(6) 0.7431(3) 0.0447(3) 0.1141(17) Uani 1 1 d . . . . .
F9 F 0.1233(6) 0.7431(4) 0.1659(4) 0.136(2) Uani 1 1 d . . . . .
F4 F 0.6338(4) -0.1590(2) 0.3068(2) 0.0624(10) Uani 1 1 d . . . . .
F3 F 0.6648(4) -0.0724(3) 0.6039(2) 0.0638(10) Uani 1 1 d . . . . .
F1 F 0.2561(3) 0.3017(3) 0.3000(2) 0.0664(10) Uani 1 1 d . . . . .
F2 F 0.4244(3) 0.4191(3) 0.5301(2) 0.0647(10) Uani 1 1 d . . . . .
F7 F -0.0758(5) 0.7037(3) 0.1883(4) 0.125(2) Uani 1 1 d . . . . .
F5 F 0.1227(6) 0.5796(4) 0.2029(3) 0.1235(19) Uani 1 1 d . . . . .
N5 N 0.9256(4) 0.2524(3) 0.2171(3) 0.0289(9) Uani 1 1 d . . . . .
N4 N 1.0126(4) 0.3666(3) 0.1399(3) 0.0352(10) Uani 1 1 d . . . . .
H4A H 1.0169 0.4249 0.1159 0.042 Uiso 1 1 calc R U . . .
N2 N 0.7922(4) 0.0847(3) 0.1934(3) 0.0292(9) Uani 1 1 d . . . . .
N1 N 0.8376(4) 0.2224(3) 0.4183(3) 0.0315(10) Uani 1 1 d . . . . .
N3 N 1.0394(4) 0.0589(3) 0.2711(3) 0.0328(10) Uani 1 1 d . . . . .
N6 N 1.3466(5) 0.1879(4) 0.0407(3) 0.0460(12) Uani 1 1 d . . . . .
C1 C 0.6174(5) 0.2422(4) 0.3404(3) 0.0312(11) Uani 1 1 d . . . . .
C2 C 0.5019(5) 0.2422(4) 0.3007(4) 0.0375(13) Uani 1 1 d . . . . .
H2A H 0.5154 0.2019 0.2494 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3680(6) 0.3029(4) 0.3389(4) 0.0446(14) Uani 1 1 d . . . . .
C4 C 0.3401(6) 0.3641(4) 0.4140(4) 0.0468(15) Uani 1 1 d . . . . .
H4B H 0.2486 0.4058 0.4370 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4536(6) 0.3611(4) 0.4538(4) 0.0421(14) Uani 1 1 d . . . . .
C6 C 0.5917(5) 0.3015(4) 0.4197(3) 0.0323(12) Uani 1 1 d . . . . .
C7 C 0.7159(5) 0.2919(4) 0.4625(3) 0.0309(11) Uani 1 1 d . . . . .
C8 C 0.7217(6) 0.3444(4) 0.5379(4) 0.0470(14) Uani 1 1 d . . . . .
H8A H 0.6398 0.3933 0.5666 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8463(7) 0.3256(5) 0.5713(4) 0.0533(16) Uani 1 1 d . . . . .
H9A H 0.8486 0.3594 0.6234 0.064 Uiso 1 1 calc R U . . .
C10 C 0.9686(6) 0.2551(5) 0.5255(4) 0.0539(16) Uani 1 1 d . . . . .
H10A H 1.0551 0.2415 0.5454 0.065 Uiso 1 1 calc R U . . .
C11 C 0.9585(5) 0.2065(4) 0.4511(4) 0.0414(13) Uani 1 1 d . . . . .
H11A H 1.0406 0.1591 0.4208 0.050 Uiso 1 1 calc R U . . .
C12 C 0.7522(5) 0.0423(4) 0.3742(3) 0.0309(12) Uani 1 1 d . . . . .
C13 C 0.7318(5) 0.0236(4) 0.4714(4) 0.0374(13) Uani 1 1 d . . . . .
H13A H 0.7523 0.0641 0.5111 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6814(5) -0.0549(4) 0.5086(4) 0.0418(14) Uani 1 1 d . . . . .
C15 C 0.6482(6) -0.1161(4) 0.4556(4) 0.0451(15) Uani 1 1 d . . . . .
H15A H 0.6126 -0.1679 0.4828 0.054 Uiso 1 1 calc R U . . .
C17 C 0.7216(5) -0.0206(4) 0.3161(4) 0.0322(12) Uani 1 1 d . . . . .
C18 C 0.7495(5) 0.0006(4) 0.2141(4) 0.0327(12) Uani 1 1 d . . . . .
C19 C 0.7419(6) -0.0557(4) 0.1424(4) 0.0468(14) Uani 1 1 d . . . . .
H19A H 0.7124 -0.1130 0.1569 0.056 Uiso 1 1 calc R U . . .
C20 C 0.7778(6) -0.0273(4) 0.0494(4) 0.0531(16) Uani 1 1 d . . . . .
H20A H 0.7743 -0.0660 0.0010 0.064 Uiso 1 1 calc R U . . .
C21 C 0.8190(6) 0.0588(4) 0.0285(4) 0.0452(14) Uani 1 1 d . . . . .
H21A H 0.8418 0.0800 -0.0339 0.054 Uiso 1 1 calc R U . . .
C22 C 0.8257(5) 0.1122(4) 0.1014(4) 0.0381(13) Uani 1 1 d . . . . .
H22A H 0.8545 0.1698 0.0875 0.046 Uiso 1 1 calc R U . . .
C23 C 1.0864(5) -0.0392(4) 0.3021(4) 0.0423(14) Uani 1 1 d . . . . .
H23A H 1.0212 -0.0672 0.3390 0.051 Uiso 1 1 calc R U . . .
C24 C 1.2247(6) -0.0993(4) 0.2821(4) 0.0484(15) Uani 1 1 d . . . . .
H24A H 1.2527 -0.1674 0.3028 0.058 Uiso 1 1 calc R U . . .
C25 C 1.3223(6) -0.0567(4) 0.2303(4) 0.0474(15) Uani 1 1 d . . . . .
H25A H 1.4182 -0.0948 0.2185 0.057 Uiso 1 1 calc R U . . .
C26 C 1.2768(5) 0.0420(4) 0.1966(4) 0.0442(14) Uani 1 1 d . . . . .
H26A H 1.3418 0.0706 0.1603 0.053 Uiso 1 1 calc R U . . .
C27 C 1.1336(5) 0.1001(4) 0.2163(3) 0.0309(11) Uani 1 1 d . . . . .
C28 C 1.0713(5) 0.2065(4) 0.1853(3) 0.0286(11) Uani 1 1 d . . . . .
C29 C 1.1256(5) 0.2775(4) 0.1344(3) 0.0304(11) Uani 1 1 d . . . . .
C30 C 1.2656(5) 0.2758(4) 0.0801(3) 0.0331(12) Uani 1 1 d . . . . .
C31 C 1.3070(6) 0.3617(4) 0.0707(4) 0.0475(15) Uani 1 1 d . . . . .
H31A H 1.2480 0.4220 0.0996 0.057 Uiso 1 1 calc R U . . .
C32 C 1.4385(7) 0.3570(5) 0.0173(4) 0.0585(18) Uani 1 1 d . . . . .
H32A H 1.4689 0.4141 0.0095 0.070 Uiso 1 1 calc R U . . .
C33 C 1.5217(6) 0.2679(5) -0.0233(4) 0.0581(18) Uani 1 1 d . . . . .
H33A H 1.6101 0.2628 -0.0596 0.070 Uiso 1 1 calc R U . . .
C34 C 1.4736(6) 0.1854(5) -0.0101(4) 0.0579(17) Uani 1 1 d . . . . .
H34A H 1.5319 0.1243 -0.0378 0.070 Uiso 1 1 calc R U . . .
C35 C 0.8939(5) 0.3496(4) 0.1885(3) 0.0304(11) Uani 1 1 d . . . . .
C36 C 0.7549(5) 0.4309(4) 0.2029(3) 0.0355(12) Uani 1 1 d . . . . .
C41 C 0.7479(6) 0.5262(4) 0.2319(4) 0.0534(16) Uani 1 1 d . . . . .
H41A H 0.8289 0.5378 0.2427 0.064 Uiso 1 1 calc R U . . .
C40 C 0.6173(7) 0.6035(5) 0.2443(5) 0.0637(19) Uani 1 1 d . . . . .
H40A H 0.6114 0.6677 0.2625 0.076 Uiso 1 1 calc R U . . .
C39 C 0.4975(6) 0.5863(5) 0.2302(4) 0.0568(18) Uani 1 1 d . . . . .
H39A H 0.4106 0.6383 0.2398 0.068 Uiso 1 1 calc R U . . .
C38 C 0.5053(6) 0.4920(5) 0.2019(4) 0.0521(16) Uani 1 1 d . . . . .
H38A H 0.4236 0.4801 0.1928 0.063 Uiso 1 1 calc R U . . .
C37 C 0.6346(5) 0.4150(4) 0.1870(4) 0.0399(13) Uani 1 1 d . . . . .
H37A H 0.6402 0.3520 0.1661 0.048 Uiso 1 1 calc R U . . .
C16 C 0.6696(5) -0.0979(4) 0.3595(4) 0.0415(13) 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 C1 2.018(5) . ?
Ir1 C12 2.011(5) . ?
Ir1 N1 2.047(4) . ?
Ir1 N2 2.039(4) . ?
Ir1 N3 2.148(4) . ?
Ir1 N5 2.165(4) . ?
P1 F9 1.561(5) . ?
P1 F10 1.574(4) . ?
P1 F7 1.546(4) . ?
P1 F8 1.553(4) . ?
P1 F5 1.580(4) . ?
P1 F6 1.606(4) . ?
F4 C16 1.362(6) . ?
F3 C14 1.363(6) . ?
F1 C3 1.364(6) . ?
F2 C5 1.351(6) . ?
N5 C35 1.323(6) . ?
N5 C28 1.401(6) . ?
N4 C29 1.374(6) . ?
N4 C35 1.350(6) . ?
N4 H4A 0.8600 . ?
N2 C18 1.361(6) . ?
N2 C22 1.356(6) . ?
N1 C7 1.370(6) . ?
N1 C11 1.341(6) . ?
N3 C27 1.359(6) . ?
N3 C23 1.348(6) . ?
N6 C30 1.329(6) . ?
N6 C34 1.343(6) . ?
C1 C2 1.399(7) . ?
C1 C6 1.402(7) . ?
C2 C3 1.376(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.366(8) . ?
C4 C5 1.368(8) . ?
C4 H4B 0.9300 . ?
C5 C6 1.387(7) . ?
C6 C7 1.469(7) . ?
C7 C8 1.384(7) . ?
C8 C9 1.374(8) . ?
C8 H8A 0.9300 . ?
C9 C10 1.388(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.355(8) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.392(7) . ?
C12 C17 1.403(7) . ?
C13 C14 1.372(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.350(8) . ?
C15 C16 1.376(8) . ?
C15 H15A 0.9300 . ?
C17 C16 1.392(7) . ?
C17 C18 1.466(7) . ?
C18 C19 1.379(7) . ?
C19 C20 1.377(8) . ?
C19 H19A 0.9300 . ?
C20 C21 1.379(8) . ?
C20 H20A 0.9300 . ?
C21 C22 1.364(7) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 C24 1.362(7) . ?
C23 H23A 0.9300 . ?
C24 C25 1.379(7) . ?
C24 H24A 0.9300 . ?
C25 C26 1.366(7) . ?
C25 H25A 0.9300 . ?
C26 C27 1.394(6) . ?
C26 H26A 0.9300 . ?
C27 C28 1.464(6) . ?
C28 C29 1.371(6) . ?
C29 C30 1.475(6) . ?
C30 C31 1.374(7) . ?
C31 C32 1.388(7) . ?
C31 H31A 0.9300 . ?
C32 C33 1.353(8) . ?
C32 H32A 0.9300 . ?
C33 C34 1.368(8) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?
C35 C36 1.475(7) . ?
C36 C37 1.372(7) . ?
C36 C41 1.396(7) . ?
C41 C40 1.392(8) . ?
C41 H41A 0.9300 . ?
C40 C39 1.366(9) . ?
C40 H40A 0.9300 . ?
C39 C38 1.377(9) . ?
C39 H39A 0.9300 . ?
C38 C37 1.382(7) . ?
C38 H38A 0.9300 . ?
C37 H37A 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
C1 Ir1 C12 84.07(18) . . ?
C1 Ir1 N1 79.99(18) . . ?
C12 Ir1 N1 97.49(18) . . ?
C1 Ir1 N2 96.98(18) . . ?
C12 Ir1 N2 80.05(18) . . ?
N1 Ir1 N2 176.33(14) . . ?
C1 Ir1 N3 177.21(18) . . ?
C12 Ir1 N3 95.12(16) . . ?
N1 Ir1 N3 97.49(15) . . ?
N2 Ir1 N3 85.49(15) . . ?
C1 Ir1 N5 105.02(16) . . ?
C12 Ir1 N5 170.49(17) . . ?
N1 Ir1 N5 87.03(15) . . ?
N2 Ir1 N5 95.80(15) . . ?
N3 Ir1 N5 75.94(14) . . ?
F9 P1 F10 90.1(3) . . ?
F9 P1 F7 91.0(3) . . ?
F10 P1 F7 178.5(3) . . ?
F9 P1 F8 89.5(3) . . ?
F10 P1 F8 89.4(3) . . ?
F7 P1 F8 91.5(3) . . ?
F9 P1 F5 93.1(3) . . ?
F10 P1 F5 89.3(3) . . ?
F7 P1 F5 89.7(3) . . ?
F8 P1 F5 177.1(3) . . ?
F9 P1 F6 178.0(3) . . ?
F10 P1 F6 88.0(2) . . ?
F7 P1 F6 90.8(3) . . ?
F8 P1 F6 91.0(3) . . ?
F5 P1 F6 86.4(3) . . ?
C35 N5 C28 106.9(4) . . ?
C35 N5 Ir1 138.2(3) . . ?
C28 N5 Ir1 114.8(3) . . ?
C29 N4 C35 110.3(4) . . ?
C29 N4 H4A 124.8 . . ?
C35 N4 H4A 124.8 . . ?
C18 N2 C22 118.8(4) . . ?
C18 N2 Ir1 117.2(3) . . ?
C22 N2 Ir1 123.7(3) . . ?
C7 N1 C11 118.4(5) . . ?
C7 N1 Ir1 116.7(3) . . ?
C11 N1 Ir1 124.9(4) . . ?
C27 N3 C23 118.8(4) . . ?
C27 N3 Ir1 118.2(3) . . ?
C23 N3 Ir1 123.0(3) . . ?
C30 N6 C34 117.1(5) . . ?
C2 C1 C6 118.7(5) . . ?
C2 C1 Ir1 126.5(4) . . ?
C6 C1 Ir1 114.6(4) . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
F1 C3 C4 117.9(5) . . ?
F1 C3 C2 118.3(5) . . ?
C4 C3 C2 123.8(5) . . ?
C3 C4 C5 116.6(5) . . ?
C3 C4 H4B 121.7 . . ?
C5 C4 H4B 121.7 . . ?
F2 C5 C6 120.8(5) . . ?
F2 C5 C4 116.2(5) . . ?
C6 C5 C4 123.0(5) . . ?
C5 C6 C1 119.0(5) . . ?
C5 C6 C7 125.0(5) . . ?
C1 C6 C7 116.0(4) . . ?
N1 C7 C8 119.3(5) . . ?
N1 C7 C6 112.7(4) . . ?
C8 C7 C6 127.9(5) . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
C10 C9 C8 118.6(6) . . ?
C10 C9 H9A 120.7 . . ?
C8 C9 H9A 120.7 . . ?
C11 C10 C9 118.2(5) . . ?
C11 C10 H10A 120.9 . . ?
C9 C10 H10A 120.9 . . ?
C10 C11 N1 124.2(5) . . ?
C10 C11 H11A 117.9 . . ?
N1 C11 H11A 117.9 . . ?
C13 C12 C17 118.9(5) . . ?
C13 C12 Ir1 127.1(4) . . ?
C17 C12 Ir1 114.0(3) . . ?
C14 C13 C12 119.7(5) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C15 C14 C13 123.5(5) . . ?
C15 C14 F3 118.2(5) . . ?
C13 C14 F3 118.3(5) . . ?
C14 C15 C16 116.7(5) . . ?
C14 C15 H15A 121.7 . . ?
C16 C15 H15A 121.7 . . ?
C16 C17 C12 117.8(5) . . ?
C16 C17 C18 125.7(5) . . ?
C12 C17 C18 116.5(4) . . ?
N2 C18 C19 120.2(5) . . ?
N2 C18 C17 112.1(4) . . ?
C19 C18 C17 127.6(5) . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
C19 C20 C21 119.5(6) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C22 C21 C20 118.5(5) . . ?
C22 C21 H21A 120.8 . . ?
C20 C21 H21A 120.8 . . ?
N2 C22 C21 122.8(5) . . ?
N2 C22 H22A 118.6 . . ?
C21 C22 H22A 118.6 . . ?
N3 C23 C24 123.2(5) . . ?
N3 C23 H23A 118.4 . . ?
C24 C23 H23A 118.4 . . ?
C23 C24 C25 118.4(5) . . ?
C23 C24 H24A 120.8 . . ?
C25 C24 H24A 120.8 . . ?
C26 C25 C24 119.4(5) . . ?
C26 C25 H25A 120.3 . . ?
C24 C25 H25A 120.3 . . ?
C25 C26 C27 120.4(5) . . ?
C25 C26 H26A 119.8 . . ?
C27 C26 H26A 119.8 . . ?
N3 C27 C26 119.7(4) . . ?
N3 C27 C28 114.4(4) . . ?
C26 C27 C28 125.9(4) . . ?
C29 C28 N5 109.2(4) . . ?
C29 C28 C27 134.1(4) . . ?
N5 C28 C27 116.7(4) . . ?
C28 C29 N4 104.5(4) . . ?
C28 C29 C30 135.2(5) . . ?
N4 C29 C30 120.2(4) . . ?
N6 C30 C31 122.8(5) . . ?
N6 C30 C29 116.3(4) . . ?
C31 C30 C29 121.0(5) . . ?
C30 C31 C32 118.8(5) . . ?
C30 C31 H31A 120.6 . . ?
C32 C31 H31A 120.6 . . ?
C33 C32 C31 118.9(6) . . ?
C33 C32 H32A 120.5 . . ?
C31 C32 H32A 120.5 . . ?
C32 C33 C34 118.9(5) . . ?
C32 C33 H33A 120.6 . . ?
C34 C33 H33A 120.6 . . ?
C33 C34 N6 123.5(6) . . ?
C33 C34 H34A 118.2 . . ?
N6 C34 H34A 118.2 . . ?
N5 C35 N4 109.0(4) . . ?
N5 C35 C36 128.6(4) . . ?
N4 C35 C36 122.3(4) . . ?
C37 C36 C41 120.0(5) . . ?
C37 C36 C35 121.4(5) . . ?
C41 C36 C35 118.5(5) . . ?
C40 C41 C36 118.7(6) . . ?
C40 C41 H41A 120.7 . . ?
C36 C41 H41A 120.7 . . ?
C39 C40 C41 120.9(6) . . ?
C39 C40 H40A 119.6 . . ?
C41 C40 H40A 119.6 . . ?
C38 C39 C40 120.0(6) . . ?
C38 C39 H39A 120.0 . . ?
C40 C39 H39A 120.0 . . ?
C39 C38 C37 119.9(6) . . ?
C39 C38 H38A 120.0 . . ?
C37 C38 H38A 120.0 . . ?
C36 C37 C38 120.4(6) . . ?
C36 C37 H37A 119.8 . . ?
C38 C37 H37A 119.8 . . ?
C15 C16 F4 116.2(5) . . ?
C15 C16 C17 123.5(5) . . ?
F4 C16 C17 120.3(5) . . ?

_refine_diff_density_max         0.720
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.110

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1550507'
_audit_update_record             
;
2017-05-16 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H25 F4 Ir N6'
_chemical_formula_sum            'C41 H25 F4 Ir N6'
_chemical_formula_weight         869.87

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'
F F 0.0171 0.0103 '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                   21.8943(8)
_cell_length_b                   24.2539(9)
_cell_length_c                   13.4991(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.3900(10)
_cell_angle_gamma                90
_cell_volume                     7155.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    20663
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.52

_exptl_crystal_description       blocky
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             3408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    3.791
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.435
_exptl_absorpt_correction_T_max  0.545
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruke Smart Aepex CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31486
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.686
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             8195
_reflns_number_gt                7315
_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, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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. 
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.500 0.579 0.250 266.4 3.9
2 1.000 0.079 0.250 266.4 3.9
3 0.500 0.421 0.750 266.5 3.7
4 1.000 0.921 0.750 266.5 3.7
_platon_squeeze_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)+(0.0450P)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         8195
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0198
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0605
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.006
_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 0.84582(2) 0.36225(2) 0.32957(2) 0.01421(4) Uani 1 1 d . . . . .
F1 F 0.62800(7) 0.44870(7) 0.19467(13) 0.0399(4) Uani 1 1 d . . . . .
F2 F 0.73208(8) 0.33726(7) -0.02185(11) 0.0419(4) Uani 1 1 d . . . . .
F3 F 0.95838(7) 0.50263(6) 0.08906(13) 0.0398(4) Uani 1 1 d . . . . .
F4 F 0.86041(7) 0.57850(6) 0.35681(13) 0.0352(4) Uani 1 1 d . . . . .
N1 N 0.86959(8) 0.31562(7) 0.21196(14) 0.0187(4) Uani 1 1 d . . . . .
N2 N 0.81688(8) 0.41293(8) 0.43817(14) 0.0182(4) Uani 1 1 d . . . . .
N3 N 0.92515(9) 0.34896(8) 0.42821(15) 0.0182(4) Uani 1 1 d . . . . .
N4 N 0.82903(8) 0.28357(7) 0.39652(13) 0.0165(4) Uani 1 1 d . . . . .
N5 N 0.81744(8) 0.19122(8) 0.40374(14) 0.0206(4) Uani 1 1 d . . . . .
N6 N 0.96955(9) 0.17272(9) 0.52606(18) 0.0315(5) Uani 1 1 d . . . . .
C1 C 0.77184(11) 0.37498(10) 0.23697(18) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.72146(10) 0.40895(9) 0.25266(18) 0.0217(5) Uani 1 1 d . . . . .
H2A H 0.7186 0.4269 0.3131 0.026 Uiso 1 1 calc R U . . .
C3 C 0.67619(12) 0.41556(10) 0.17823(19) 0.0264(5) Uani 1 1 d . . . . .
C4 C 0.67878(12) 0.39223(11) 0.0853(2) 0.0311(6) Uani 1 1 d . . . . .
H4A H 0.6484 0.3983 0.0355 0.037 Uiso 1 1 calc R U . . .
C5 C 0.72870(13) 0.35954(10) 0.0703(2) 0.0279(6) Uani 1 1 d . . . . .
C6 C 0.77511(11) 0.34913(10) 0.14277(18) 0.0221(5) Uani 1 1 d . . . . .
C7 C 0.82854(10) 0.31377(9) 0.13153(17) 0.0225(5) Uani 1 1 d . . . . .
C8 C 0.83965(13) 0.27869(11) 0.05255(19) 0.0334(6) Uani 1 1 d . . . . .
H8A H 0.8116 0.2766 -0.0018 0.040 Uiso 1 1 calc R U . . .
C9 C 0.89192(13) 0.24733(12) 0.0549(2) 0.0372(6) Uani 1 1 d . . . . .
H9A H 0.8992 0.2240 0.0023 0.045 Uiso 1 1 calc R U . . .
C10 C 0.93372(12) 0.25041(11) 0.1353(2) 0.0312(6) Uani 1 1 d . . . . .
H10A H 0.9698 0.2301 0.1371 0.037 Uiso 1 1 calc R U . . .
C11 C 0.92044(11) 0.28445(10) 0.21280(18) 0.0235(5) Uani 1 1 d . . . . .
H11A H 0.9478 0.2860 0.2681 0.028 Uiso 1 1 calc R U . . .
C12 C 0.87436(10) 0.43466(9) 0.27835(17) 0.0177(4) Uani 1 1 d . . . . .
C13 C 0.90822(11) 0.44293(9) 0.19518(19) 0.0244(5) Uani 1 1 d . . . . .
H13A H 0.9189 0.4132 0.1563 0.029 Uiso 1 1 calc R U . . .
C14 C 0.92571(11) 0.49581(10) 0.1712(2) 0.0283(5) Uani 1 1 d . . . . .
C15 C 0.91067(11) 0.54169(10) 0.2230(2) 0.0293(6) Uani 1 1 d . . . . .
H15A H 0.9226 0.5768 0.2045 0.035 Uiso 1 1 calc R U . . .
C16 C 0.87668(11) 0.53283(9) 0.3043(2) 0.0253(5) Uani 1 1 d . . . . .
C17 C 0.85821(10) 0.48075(10) 0.33543(17) 0.0207(5) Uani 1 1 d . . . . .
C18 C 0.82606(10) 0.46846(9) 0.42502(18) 0.0213(5) Uani 1 1 d . . . . .
C19 C 0.80658(11) 0.50532(10) 0.49577(19) 0.0278(5) Uani 1 1 d . . . . .
H19A H 0.8124 0.5430 0.4873 0.033 Uiso 1 1 calc R U . . .
C20 C 0.77877(11) 0.48641(11) 0.57829(19) 0.0298(6) Uani 1 1 d . . . . .
H20A H 0.7657 0.5111 0.6253 0.036 Uiso 1 1 calc R U . . .
C21 C 0.77054(11) 0.42981(10) 0.59034(19) 0.0265(5) Uani 1 1 d . . . . .
H21A H 0.7523 0.4160 0.6457 0.032 Uiso 1 1 calc R U . . .
C22 C 0.79009(10) 0.39469(10) 0.51814(18) 0.0226(5) Uani 1 1 d . . . . .
H22A H 0.7844 0.3570 0.5255 0.027 Uiso 1 1 calc R U . . .
C23 C 0.96607(10) 0.38898(9) 0.45322(18) 0.0219(5) Uani 1 1 d . . . . .
H23A H 0.9652 0.4212 0.4157 0.026 Uiso 1 1 calc R U . . .
C24 C 1.00881(11) 0.38457(10) 0.53110(19) 0.0251(5) Uani 1 1 d . . . . .
H24A H 1.0373 0.4124 0.5447 0.030 Uiso 1 1 calc R U . . .
C25 C 1.00830(11) 0.33747(10) 0.58904(19) 0.0269(5) Uani 1 1 d . . . . .
H25A H 1.0352 0.3342 0.6447 0.032 Uiso 1 1 calc R U . . .
C26 C 0.96790(10) 0.29549(10) 0.56413(18) 0.0239(5) Uani 1 1 d . . . . .
H26A H 0.9681 0.2634 0.6019 0.029 Uiso 1 1 calc R U . . .
C27 C 0.92655(10) 0.30126(9) 0.48180(16) 0.0186(4) Uani 1 1 d . . . . .
C28 C 0.87980(10) 0.26163(9) 0.44828(16) 0.0181(4) Uani 1 1 d . . . . .
C29 C 0.87274(10) 0.20464(9) 0.45145(17) 0.0209(5) Uani 1 1 d . . . . .
C30 C 0.91142(10) 0.16049(10) 0.49552(18) 0.0234(5) Uani 1 1 d . . . . .
C31 C 0.88690(12) 0.10774(11) 0.5067(2) 0.0375(7) Uani 1 1 d . . . . .
H31A H 0.8467 0.1002 0.4848 0.045 Uiso 1 1 calc R U . . .
C32 C 0.92311(15) 0.06703(12) 0.5508(3) 0.0509(9) Uani 1 1 d . . . . .
H32A H 0.9076 0.0317 0.5589 0.061 Uiso 1 1 calc R U . . .
C33 C 0.98274(14) 0.07928(12) 0.5828(3) 0.0490(9) Uani 1 1 d . . . . .
H33A H 1.0083 0.0526 0.6125 0.059 Uiso 1 1 calc R U . . .
C34 C 1.00302(13) 0.13237(11) 0.5692(3) 0.0384(7) Uani 1 1 d . . . . .
H34A H 1.0429 0.1407 0.5916 0.046 Uiso 1 1 calc R U . . .
C35 C 0.79331(10) 0.23910(9) 0.37278(16) 0.0179(4) Uani 1 1 d . . . . .
C36 C 0.73278(10) 0.24350(9) 0.32010(16) 0.0186(4) Uani 1 1 d . . . . .
C37 C 0.69389(10) 0.28754(9) 0.33762(17) 0.0208(4) Uani 1 1 d . . . . .
H37A H 0.7060 0.3142 0.3842 0.025 Uiso 1 1 calc R U . . .
C38 C 0.63729(10) 0.29203(9) 0.28628(18) 0.0230(5) Uani 1 1 d . . . . .
H38A H 0.6121 0.3219 0.2977 0.028 Uiso 1 1 calc R U . . .
C39 C 0.61840(11) 0.25201(10) 0.21804(19) 0.0271(5) Uani 1 1 d . . . . .
H39A H 0.5805 0.2549 0.1835 0.033 Uiso 1 1 calc R U . . .
C40 C 0.65625(11) 0.20771(11) 0.2015(2) 0.0312(6) Uani 1 1 d . . . . .
H40A H 0.6434 0.1806 0.1562 0.037 Uiso 1 1 calc R U . . .
C41 C 0.71314(11) 0.20322(9) 0.25175(18) 0.0246(5) Uani 1 1 d . . . . .
H41A H 0.7382 0.1733 0.2398 0.029 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 C12 2.001(2) . ?
Ir1 C1 2.010(2) . ?
Ir1 N2 2.0425(19) . ?
Ir1 N1 2.0416(19) . ?
Ir1 N3 2.1493(19) . ?
Ir1 N4 2.1524(18) . ?
F1 C3 1.355(3) . ?
F2 C5 1.362(3) . ?
F3 C14 1.364(3) . ?
F4 C16 1.373(3) . ?
N1 C11 1.345(3) . ?
N1 C7 1.369(3) . ?
N2 C22 1.334(3) . ?
N2 C18 1.375(3) . ?
N3 C23 1.350(3) . ?
N3 C27 1.364(3) . ?
N4 C35 1.359(3) . ?
N4 C28 1.384(3) . ?
N5 C35 1.333(3) . ?
N5 C29 1.376(3) . ?
N6 C34 1.335(3) . ?
N6 C30 1.348(3) . ?
C1 C2 1.403(4) . ?
C1 C6 1.423(3) . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(4) . ?
C4 C5 1.375(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(3) . ?
C6 C7 1.466(3) . ?
C7 C8 1.397(3) . ?
C8 C9 1.373(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.379(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.396(3) . ?
C12 C17 1.414(3) . ?
C13 C14 1.382(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.365(4) . ?
C15 C16 1.379(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.398(3) . ?
C17 C18 1.465(3) . ?
C18 C19 1.393(3) . ?
C19 C20 1.379(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.395(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.381(3) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 C24 1.370(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.385(4) . ?
C24 H24A 0.9300 . ?
C25 C26 1.377(3) . ?
C25 H25A 0.9300 . ?
C26 C27 1.398(3) . ?
C26 H26A 0.9300 . ?
C27 C28 1.457(3) . ?
C28 C29 1.392(3) . ?
C29 C30 1.469(3) . ?
C30 C31 1.399(3) . ?
C31 C32 1.379(4) . ?
C31 H31A 0.9300 . ?
C32 C33 1.383(4) . ?
C32 H32A 0.9300 . ?
C33 C34 1.378(4) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?
C35 C36 1.470(3) . ?
C36 C41 1.394(3) . ?
C36 C37 1.395(3) . ?
C37 C38 1.388(3) . ?
C37 H37A 0.9300 . ?
C38 C39 1.384(3) . ?
C38 H38A 0.9300 . ?
C39 C40 1.383(4) . ?
C39 H39A 0.9300 . ?
C40 C41 1.387(3) . ?
C40 H40A 0.9300 . ?
C41 H41A 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
C12 Ir1 C1 84.66(9) . . ?
C12 Ir1 N2 80.58(8) . . ?
C1 Ir1 N2 94.65(9) . . ?
C12 Ir1 N1 96.79(8) . . ?
C1 Ir1 N1 80.48(9) . . ?
N2 Ir1 N1 174.70(7) . . ?
C12 Ir1 N3 95.07(8) . . ?
C1 Ir1 N3 179.71(8) . . ?
N2 Ir1 N3 85.37(7) . . ?
N1 Ir1 N3 99.49(7) . . ?
C12 Ir1 N4 171.05(7) . . ?
C1 Ir1 N4 104.24(8) . . ?
N2 Ir1 N4 99.46(7) . . ?
N1 Ir1 N4 83.86(7) . . ?
N3 Ir1 N4 76.04(7) . . ?
C11 N1 C7 119.5(2) . . ?
C11 N1 Ir1 123.61(15) . . ?
C7 N1 Ir1 116.72(15) . . ?
C22 N2 C18 120.3(2) . . ?
C22 N2 Ir1 123.44(15) . . ?
C18 N2 Ir1 116.29(16) . . ?
C23 N3 C27 118.90(19) . . ?
C23 N3 Ir1 123.16(16) . . ?
C27 N3 Ir1 116.61(14) . . ?
C35 N4 C28 104.35(17) . . ?
C35 N4 Ir1 135.61(14) . . ?
C28 N4 Ir1 113.63(14) . . ?
C35 N5 C29 105.19(18) . . ?
C34 N6 C30 117.1(2) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 Ir1 127.45(19) . . ?
C6 C1 Ir1 113.99(17) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
F1 C3 C2 118.9(2) . . ?
F1 C3 C4 117.8(2) . . ?
C2 C3 C4 123.3(2) . . ?
C5 C4 C3 116.5(2) . . ?
C5 C4 H4A 121.8 . . ?
C3 C4 H4A 121.8 . . ?
F2 C5 C4 116.7(2) . . ?
F2 C5 C6 119.6(2) . . ?
C4 C5 C6 123.7(3) . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 126.0(2) . . ?
C1 C6 C7 115.7(2) . . ?
N1 C7 C8 119.3(2) . . ?
N1 C7 C6 112.9(2) . . ?
C8 C7 C6 127.7(2) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C11 118.0(2) . . ?
C9 C10 H10A 121.0 . . ?
C11 C10 H10A 121.0 . . ?
N1 C11 C10 122.8(2) . . ?
N1 C11 H11A 118.6 . . ?
C10 C11 H11A 118.6 . . ?
C13 C12 C17 119.1(2) . . ?
C13 C12 Ir1 126.55(17) . . ?
C17 C12 Ir1 114.34(17) . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
F3 C14 C15 118.1(2) . . ?
F3 C14 C13 117.9(2) . . ?
C15 C14 C13 123.9(3) . . ?
C14 C15 C16 116.0(2) . . ?
C14 C15 H15A 122.0 . . ?
C16 C15 H15A 122.0 . . ?
F4 C16 C15 117.0(2) . . ?
F4 C16 C17 119.0(2) . . ?
C15 C16 C17 124.0(2) . . ?
C16 C17 C12 117.7(2) . . ?
C16 C17 C18 126.4(2) . . ?
C12 C17 C18 115.9(2) . . ?
N2 C18 C19 119.1(2) . . ?
N2 C18 C17 112.8(2) . . ?
C19 C18 C17 128.1(2) . . ?
C20 C19 C18 120.5(2) . . ?
C20 C19 H19A 119.7 . . ?
C18 C19 H19A 119.7 . . ?
C19 C20 C21 119.2(2) . . ?
C19 C20 H20A 120.4 . . ?
C21 C20 H20A 120.4 . . ?
C20 C21 C22 118.5(2) . . ?
C20 C21 H21A 120.8 . . ?
C22 C21 H21A 120.8 . . ?
N2 C22 C21 122.4(2) . . ?
N2 C22 H22A 118.8 . . ?
C21 C22 H22A 118.8 . . ?
N3 C23 C24 123.3(2) . . ?
N3 C23 H23A 118.4 . . ?
C24 C23 H23A 118.4 . . ?
C23 C24 C25 118.0(2) . . ?
C23 C24 H24A 121.0 . . ?
C25 C24 H24A 121.0 . . ?
C26 C25 C24 119.9(2) . . ?
C26 C25 H25A 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C25 C26 C27 119.7(2) . . ?
C25 C26 H26A 120.1 . . ?
C27 C26 H26A 120.1 . . ?
N3 C27 C26 119.99(19) . . ?
N3 C27 C28 113.68(18) . . ?
C26 C27 C28 126.2(2) . . ?
N4 C28 C29 108.06(18) . . ?
N4 C28 C27 115.59(18) . . ?
C29 C28 C27 136.3(2) . . ?
N5 C29 C28 108.46(19) . . ?
N5 C29 C30 119.2(2) . . ?
C28 C29 C30 132.4(2) . . ?
N6 C30 C31 122.0(2) . . ?
N6 C30 C29 118.4(2) . . ?
C31 C30 C29 119.6(2) . . ?
C32 C31 C30 119.1(3) . . ?
C32 C31 H31A 120.4 . . ?
C30 C31 H31A 120.4 . . ?
C31 C32 C33 119.3(3) . . ?
C31 C32 H32A 120.4 . . ?
C33 C32 H32A 120.4 . . ?
C34 C33 C32 117.7(3) . . ?
C34 C33 H33A 121.2 . . ?
C32 C33 H33A 121.2 . . ?
N6 C34 C33 124.8(3) . . ?
N6 C34 H34A 117.6 . . ?
C33 C34 H34A 117.6 . . ?
N5 C35 N4 113.92(19) . . ?
N5 C35 C36 122.96(19) . . ?
N4 C35 C36 123.10(19) . . ?
C41 C36 C37 118.8(2) . . ?
C41 C36 C35 120.2(2) . . ?
C37 C36 C35 121.0(2) . . ?
C38 C37 C36 120.8(2) . . ?
C38 C37 H37A 119.6 . . ?
C36 C37 H37A 119.6 . . ?
C39 C38 C37 120.0(2) . . ?
C39 C38 H38A 120.0 . . ?
C37 C38 H38A 120.0 . . ?
C38 C39 C40 119.6(2) . . ?
C38 C39 H39A 120.2 . . ?
C40 C39 H39A 120.2 . . ?
C39 C40 C41 120.8(2) . . ?
C39 C40 H40A 119.6 . . ?
C41 C40 H40A 119.6 . . ?
C40 C41 C36 120.1(2) . . ?
C40 C41 H41A 120.0 . . ?
C36 C41 H41A 120.0 . . ?

_refine_diff_density_max         1.169
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.082

_shelxl_version_number           2014/6

