# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ab95
_database_code_depnum_ccdc_archive 'CCDC 1019226'
_audit_update_record             
;
2014-08-13 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N'
_chemical_formula_sum            'C23 H17 N'
_chemical_formula_weight         307.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   7.4701(2)
_cell_length_b                   19.7919(5)
_cell_length_c                   11.1894(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1654.32(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4881
_cell_measurement_theta_min      4.47
_cell_measurement_theta_max      67.70

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.544
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            11157
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.468
_diffrn_reflns_theta_max         68.023
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2874
_reflns_number_gt                2734
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_max     0.914
_reflns_Friedel_fraction_full    0.941

_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0631P)²+0.0887P] 
 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_abs_structure_details 
; 
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.051
_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
N1 N 0.8114(4) 0.29581(11) 0.7178(2) 0.0825(6) Uani 1 1 d . . . . .
C1 C 0.8131(5) 0.35536(14) 0.7795(3) 0.0880(8) Uani 1 1 d . . . . .
H1A H 0.8552 0.3556 0.8577 0.106 Uiso 1 1 calc R U . . .
C2 C 0.7547(4) 0.41492(15) 0.7299(3) 0.0873(9) Uani 1 1 d . . . . .
H2A H 0.7568 0.4548 0.7738 0.105 Uiso 1 1 calc R U . . .
C3 C 0.6936(4) 0.41442(12) 0.6153(3) 0.0810(8) Uani 1 1 d . . . . .
H3A H 0.6525 0.4542 0.5807 0.097 Uiso 1 1 calc R U . . .
C4 C 0.6924(3) 0.35521(11) 0.5502(2) 0.0646(6) Uani 1 1 d . . . . .
H4A H 0.6517 0.3551 0.4716 0.077 Uiso 1 1 calc R U . . .
C5 C 0.7522(3) 0.29586(10) 0.6025(2) 0.0537(5) Uani 1 1 d . . . . .
C6 C 0.7525(3) 0.23128(10) 0.5350(2) 0.0509(5) Uani 1 1 d . . . . .
C7 C 0.7801(3) 0.22993(10) 0.41206(19) 0.0515(5) Uani 1 1 d . . . . .
H7A H 0.7991 0.2703 0.3715 0.062 Uiso 1 1 calc R U . . .
C8 C 0.7798(3) 0.16937(10) 0.34830(19) 0.0497(5) Uani 1 1 d . . . . .
C9 C 0.7513(3) 0.10966(10) 0.41044(19) 0.0514(5) Uani 1 1 d . . . . .
H9A H 0.7512 0.0690 0.3688 0.062 Uiso 1 1 calc R U . . .
C10 C 0.7228(3) 0.10900(10) 0.53340(19) 0.0502(5) Uani 1 1 d . . . . .
C11 C 0.7244(3) 0.17018(10) 0.5939(2) 0.0528(5) Uani 1 1 d . . . . .
H11A H 0.7063 0.1704 0.6761 0.063 Uiso 1 1 calc R U . . .
C12 C 0.8111(3) 0.16879(9) 0.2169(2) 0.0499(4) Uani 1 1 d . . . . .
C13 C 0.7389(3) 0.21824(12) 0.1434(2) 0.0604(6) Uani 1 1 d . . . . .
H13A H 0.6703 0.2527 0.1765 0.072 Uiso 1 1 calc R U . . .
C14 C 0.7682(4) 0.21672(14) 0.0215(2) 0.0753(7) Uani 1 1 d . . . . .
H14A H 0.7176 0.2498 -0.0270 0.090 Uiso 1 1 calc R U . . .
C15 C 0.8723(4) 0.16638(14) -0.0290(2) 0.0777(7) Uani 1 1 d . . . . .
H15A H 0.8939 0.1659 -0.1108 0.093 Uiso 1 1 calc R U . . .
C16 C 0.9428(4) 0.11756(13) 0.0431(2) 0.0761(7) Uani 1 1 d . . . . .
H16A H 1.0122 0.0834 0.0099 0.091 Uiso 1 1 calc R U . . .
C17 C 0.9122(3) 0.11836(11) 0.1647(2) 0.0609(5) Uani 1 1 d . . . . .
H17A H 0.9604 0.0844 0.2123 0.073 Uiso 1 1 calc R U . . .
C18 C 0.6881(3) 0.04471(10) 0.5983(2) 0.0539(5) Uani 1 1 d . . . . .
C19 C 0.6020(3) -0.00756(10) 0.5414(2) 0.0623(5) Uani 1 1 d . . . . .
H19A H 0.5686 -0.0034 0.4616 0.075 Uiso 1 1 calc R U . . .
C20 C 0.5656(4) -0.06602(12) 0.6031(3) 0.0790(7) Uani 1 1 d . . . . .
H20A H 0.5063 -0.1011 0.5646 0.095 Uiso 1 1 calc R U . . .
C21 C 0.6146(4) -0.07357(13) 0.7195(3) 0.0826(8) Uani 1 1 d . . . . .
H21A H 0.5891 -0.1133 0.7604 0.099 Uiso 1 1 calc R U . . .
C22 C 0.7018(4) -0.02174(15) 0.7750(3) 0.0831(8) Uani 1 1 d . . . . .
H22A H 0.7364 -0.0264 0.8544 0.100 Uiso 1 1 calc R U . . .
C23 C 0.7392(3) 0.03717(12) 0.7153(2) 0.0672(6) Uani 1 1 d . . . . .
H23A H 0.7991 0.0720 0.7541 0.081 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
N1 C5 1.364(3) . ?
N1 C1 1.366(3) . ?
C1 C2 1.374(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.361(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.485(3) . ?
C6 C7 1.391(3) . ?
C6 C11 1.393(3) . ?
C7 C8 1.395(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.388(3) . ?
C8 C12 1.489(3) . ?
C9 C10 1.392(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.387(3) . ?
C10 C18 1.488(3) . ?
C11 H11A 0.9300 . ?
C12 C17 1.381(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.382(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.384(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.364(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.380(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C23 1.372(3) . ?
C18 C19 1.375(3) . ?
C19 C20 1.375(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.360(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.365(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.373(4) . ?
C22 H22A 0.9300 . ?
C23 H23A 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
C5 N1 C1 118.7(3) . . ?
N1 C1 C2 122.2(3) . . ?
N1 C1 H1A 118.9 . . ?
C2 C1 H1A 118.9 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
N1 C5 C4 120.3(2) . . ?
N1 C5 C6 118.7(2) . . ?
C4 C5 C6 121.0(2) . . ?
C7 C6 C11 118.24(18) . . ?
C7 C6 C5 121.31(18) . . ?
C11 C6 C5 120.4(2) . . ?
C6 C7 C8 121.46(18) . . ?
C6 C7 H7A 119.3 . . ?
C8 C7 H7A 119.3 . . ?
C9 C8 C7 118.41(19) . . ?
C9 C8 C12 120.83(18) . . ?
C7 C8 C12 120.76(18) . . ?
C8 C9 C10 121.78(19) . . ?
C8 C9 H9A 119.1 . . ?
C10 C9 H9A 119.1 . . ?
C11 C10 C9 118.19(19) . . ?
C11 C10 C18 120.68(18) . . ?
C9 C10 C18 121.12(18) . . ?
C10 C11 C6 121.9(2) . . ?
C10 C11 H11A 119.0 . . ?
C6 C11 H11A 119.0 . . ?
C17 C12 C13 118.2(2) . . ?
C17 C12 C8 120.59(19) . . ?
C13 C12 C8 121.25(19) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C16 C15 C14 119.1(2) . . ?
C16 C15 H15A 120.5 . . ?
C14 C15 H15A 120.5 . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C12 C17 C16 121.1(2) . . ?
C12 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C23 C18 C19 119.4(2) . . ?
C23 C18 C10 120.7(2) . . ?
C19 C18 C10 119.9(2) . . ?
C18 C19 C20 119.5(2) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C21 C20 C19 121.4(2) . . ?
C21 C20 H20A 119.3 . . ?
C19 C20 H20A 119.3 . . ?
C20 C21 C22 118.8(2) . . ?
C20 C21 H21A 120.6 . . ?
C22 C21 H21A 120.6 . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22A 119.5 . . ?
C23 C22 H22A 119.5 . . ?
C18 C23 C22 120.0(3) . . ?
C18 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.026

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_3s
_database_code_depnum_ccdc_archive 'CCDC 1019227'
_audit_update_record             
;
2014-08-13 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H40 Ir N4, F6 P, C2 H6 O'
_chemical_formula_sum            'C58 H46 F6 Ir N4 O P'
_chemical_formula_weight         1152.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   13.1280(6)
_cell_length_b                   37.8916(17)
_cell_length_c                   10.2900(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5118.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      69.19

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    5.901
_shelx_estimated_absorpt_T_min   0.492
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_T_max  0.838
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            48035
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.366
_diffrn_reflns_theta_max         69.362
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9189
_reflns_number_gt                8655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    1.000

_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0710P)²+15.0647P] 
 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_abs_structure_details 
; 
 Flack x determined using 3716 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.016(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9189
_refine_ls_number_parameters     670
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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 0.08626(2) 0.35753(2) 0.75125(8) 0.02122(13) Uani 1 1 d . . . . .
N1 N 0.1490(7) 0.3194(2) 0.6228(9) 0.0259(18) Uani 1 1 d . . . . .
N2 N -0.0174(6) 0.31377(19) 0.7680(10) 0.0240(18) Uani 1 1 d . . . . .
C1 C 0.2371(8) 0.3233(3) 0.5547(10) 0.030(2) Uani 1 1 d . . . . .
H1A H 0.2724 0.3451 0.5598 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2768(11) 0.2968(3) 0.4786(12) 0.035(3) Uani 1 1 d . . . . .
H2A H 0.3386 0.3003 0.4324 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2258(10) 0.2653(3) 0.4704(12) 0.041(3) Uani 1 1 d . . . . .
H3A H 0.2524 0.2466 0.4193 0.050 Uiso 1 1 calc R U . . .
C4 C 0.1337(9) 0.2610(3) 0.5385(12) 0.040(3) Uani 1 1 d . . . . .
H4A H 0.0965 0.2396 0.5330 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0992(7) 0.2884(3) 0.6124(10) 0.026(2) Uani 1 1 d . . . . .
C6 C 0.0042(8) 0.2863(2) 0.6913(10) 0.026(2) Uani 1 1 d . . . . .
C7 C -0.0588(10) 0.2562(3) 0.6881(13) 0.041(3) Uani 1 1 d . . . . .
H7A H -0.0449 0.2375 0.6293 0.049 Uiso 1 1 calc R U . . .
C8 C -0.1404(9) 0.2543(3) 0.7709(14) 0.040(3) Uani 1 1 d . . . . .
H8A H -0.1821 0.2338 0.7731 0.048 Uiso 1 1 calc R U . . .
C9 C -0.1610(8) 0.2831(3) 0.8521(11) 0.035(2) Uani 1 1 d . . . . .
H9A H -0.2175 0.2825 0.9097 0.042 Uiso 1 1 calc R U . . .
C10 C -0.0987(8) 0.3119(3) 0.8473(11) 0.029(2) Uani 1 1 d . . . . .
H10A H -0.1134 0.3314 0.9021 0.035 Uiso 1 1 calc R U . . .
N3 N -0.0187(6) 0.3767(2) 0.6228(9) 0.0240(19) Uani 1 1 d . . . . .
C11 C -0.0166(9) 0.3720(3) 0.4960(10) 0.028(2) Uani 1 1 d . . . . .
H11A H 0.0419 0.3614 0.4581 0.034 Uiso 1 1 calc R U . . .
C12 C -0.0984(8) 0.3820(3) 0.4140(11) 0.031(2) Uani 1 1 d . . . . .
H12A H -0.0958 0.3784 0.3227 0.037 Uiso 1 1 calc R U . . .
C13 C -0.1814(9) 0.3972(3) 0.4723(11) 0.034(2) Uani 1 1 d . . . . .
H13A H -0.2379 0.4040 0.4203 0.041 Uiso 1 1 calc R U . . .
C14 C -0.1847(9) 0.4028(3) 0.6012(13) 0.031(3) Uani 1 1 d . . . . .
H14A H -0.2423 0.4138 0.6395 0.038 Uiso 1 1 calc R U . . .
C15 C -0.1020(9) 0.3921(3) 0.6792(14) 0.024(3) Uani 1 1 d . . . . .
C16 C -0.0920(9) 0.3976(4) 0.8188(15) 0.028(3) Uani 1 1 d . . . . .
C17 C 0.0064(7) 0.3891(2) 0.8735(9) 0.0175(19) Uani 1 1 d . . . . .
C18 C 0.0245(7) 0.4010(2) 1.0008(10) 0.024(2) Uani 1 1 d . . . . .
C19 C -0.0531(7) 0.4162(2) 1.0746(10) 0.0230(19) Uani 1 1 d . . . . .
H19A H -0.0389 0.4235 1.1611 0.028 Uiso 1 1 calc R U . . .
C20 C -0.1530(7) 0.4213(2) 1.0237(11) 0.025(2) Uani 1 1 d . . . . .
C21 C -0.1683(10) 0.4126(3) 0.8922(11) 0.029(3) Uani 1 1 d . . . . .
H21A H -0.2326 0.4171 0.8533 0.034 Uiso 1 1 calc R U . . .
C22 C 0.1255(7) 0.3989(2) 1.0693(9) 0.0225(19) Uani 1 1 d . . . . .
C23 C 0.2012(8) 0.4230(3) 1.0425(11) 0.031(2) Uani 1 1 d . . . . .
H23A H 0.1913 0.4403 0.9768 0.038 Uiso 1 1 calc R U . . .
C24 C 0.2921(8) 0.4220(3) 1.1121(12) 0.032(2) Uani 1 1 d . . . . .
H24A H 0.3448 0.4383 1.0913 0.038 Uiso 1 1 calc R U . . .
C25 C 0.3071(8) 0.3978(3) 1.2111(10) 0.033(2) Uani 1 1 d . . . . .
H25A H 0.3674 0.3980 1.2620 0.040 Uiso 1 1 calc R U . . .
C26 C 0.2313(7) 0.3737(3) 1.2324(10) 0.025(2) Uani 1 1 d . . . . .
H26A H 0.2427 0.3557 1.2948 0.030 Uiso 1 1 calc R U . . .
C27 C 0.1405(8) 0.3743(3) 1.1688(10) 0.026(2) Uani 1 1 d . . . . .
H27A H 0.0879 0.3583 1.1918 0.031 Uiso 1 1 calc R U . . .
C28 C -0.2334(7) 0.4351(3) 1.1079(10) 0.028(2) Uani 1 1 d . . . . .
C29 C -0.3312(8) 0.4204(3) 1.1085(12) 0.034(2) Uani 1 1 d . . . . .
H29A H -0.3454 0.4007 1.0548 0.041 Uiso 1 1 calc R U . . .
C30 C -0.4069(8) 0.4342(4) 1.1855(15) 0.048(3) Uani 1 1 d . . . . .
H30A H -0.4718 0.4231 1.1876 0.057 Uiso 1 1 calc R U . . .
C31 C -0.3901(9) 0.4633(3) 1.258(2) 0.049(3) Uani 1 1 d . . . . .
H31A H -0.4438 0.4732 1.3083 0.059 Uiso 1 1 calc R U . . .
C32 C -0.2950(8) 0.4786(3) 1.2596(18) 0.044(3) Uani 1 1 d . . . . .
H32A H -0.2828 0.4988 1.3122 0.052 Uiso 1 1 calc R U . . .
C33 C -0.2184(8) 0.4649(3) 1.1856(11) 0.032(2) Uani 1 1 d . . . . .
H33A H -0.1534 0.4759 1.1869 0.038 Uiso 1 1 calc R U . . .
N4 N 0.1847(6) 0.3359(2) 0.8878(8) 0.0212(17) Uani 1 1 d . . . . .
C34 C 0.1609(8) 0.3087(3) 0.9642(11) 0.026(2) Uani 1 1 d . . . . .
H34A H 0.0930 0.3001 0.9640 0.031 Uiso 1 1 calc R U . . .
C35 C 0.2317(9) 0.2928(3) 1.0434(12) 0.032(3) Uani 1 1 d . . . . .
H35A H 0.2133 0.2736 1.0977 0.039 Uiso 1 1 calc R U . . .
C36 C 0.3308(8) 0.3056(3) 1.0419(12) 0.033(2) Uani 1 1 d . . . . .
H36A H 0.3818 0.2952 1.0950 0.039 Uiso 1 1 calc R U . . .
C37 C 0.3543(8) 0.3338(3) 0.9619(12) 0.033(2) Uani 1 1 d . . . . .
H37A H 0.4220 0.3426 0.9596 0.040 Uiso 1 1 calc R U . . .
C38 C 0.2808(8) 0.3492(3) 0.8858(11) 0.027(2) Uani 1 1 d . . . . .
C39 C 0.2923(7) 0.3808(3) 0.8045(10) 0.026(2) Uani 1 1 d . . . . .
C40 C 0.2049(6) 0.3924(2) 0.7305(9) 0.019(2) Uani 1 1 d . . . . .
C41 C 0.2170(8) 0.4222(2) 0.6567(10) 0.024(2) Uani 1 1 d . . . . .
C42 C 0.3122(8) 0.4391(2) 0.6489(10) 0.027(2) Uani 1 1 d . . . . .
H42A H 0.3199 0.4586 0.5916 0.033 Uiso 1 1 calc R U . . .
C43 C 0.3957(7) 0.4281(3) 0.7225(8) 0.022(2) Uani 1 1 d . . . . .
C44 C 0.3851(8) 0.3990(3) 0.8009(11) 0.029(2) Uani 1 1 d . . . . .
H44A H 0.4407 0.3912 0.8527 0.035 Uiso 1 1 calc R U . . .
C45 C 0.1348(7) 0.4405(2) 0.5832(10) 0.025(2) Uani 1 1 d . . . . .
C46 C 0.0514(8) 0.4550(2) 0.6493(11) 0.026(2) Uani 1 1 d . . . . .
H46A H 0.0443 0.4515 0.7403 0.031 Uiso 1 1 calc R U . . .
C47 C -0.0209(9) 0.4743(3) 0.5817(13) 0.040(3) Uani 1 1 d . . . . .
H47A H -0.0778 0.4839 0.6265 0.048 Uiso 1 1 calc R U . . .
C48 C -0.0107(10) 0.4799(3) 0.4486(13) 0.042(3) Uani 1 1 d . . . . .
H48A H -0.0603 0.4931 0.4025 0.051 Uiso 1 1 calc R U . . .
C49 C 0.0718(9) 0.4659(3) 0.3849(13) 0.042(3) Uani 1 1 d . . . . .
H49A H 0.0797 0.4698 0.2942 0.050 Uiso 1 1 calc R U . . .
C50 C 0.1430(9) 0.4465(3) 0.4508(11) 0.034(2) Uani 1 1 d . . . . .
H50A H 0.1992 0.4368 0.4047 0.041 Uiso 1 1 calc R U . . .
C51 C 0.4930(7) 0.4489(2) 0.7239(8) 0.022(2) Uani 1 1 d . . . . .
C52 C 0.5372(10) 0.4612(3) 0.6098(13) 0.039(3) Uani 1 1 d . . . . .
H52A H 0.5072 0.4553 0.5286 0.047 Uiso 1 1 calc R U . . .
C53 C 0.6239(11) 0.4818(4) 0.6122(13) 0.041(3) Uani 1 1 d . . . . .
H53A H 0.6524 0.4904 0.5335 0.050 Uiso 1 1 calc R U . . .
C54 C 0.6699(8) 0.4899(3) 0.7323(16) 0.039(3) Uani 1 1 d . . . . .
H54A H 0.7294 0.5042 0.7353 0.047 Uiso 1 1 calc R U . . .
C55 C 0.6286(10) 0.4773(3) 0.8422(12) 0.031(3) Uani 1 1 d . . . . .
H55A H 0.6606 0.4822 0.9230 0.037 Uiso 1 1 calc R U . . .
C56 C 0.5394(9) 0.4571(3) 0.8402(12) 0.030(3) Uani 1 1 d . . . . .
H56A H 0.5107 0.4490 0.9195 0.036 Uiso 1 1 calc R U . . .
P1 P 0.94365(19) 0.28237(6) 1.2449(5) 0.0353(5) Uani 1 1 d . . . . .
F10 F 0.8927(8) 0.2996(2) 1.3717(9) 0.067(3) Uani 1 1 d . . . . .
F11 F 0.8369(5) 0.26684(19) 1.2057(7) 0.0447(17) Uani 1 1 d . . . . .
F12 F 0.9231(6) 0.3177(2) 1.1670(9) 0.053(2) Uani 1 1 d . . . . .
F13 F 1.0509(6) 0.2979(2) 1.2903(8) 0.064(3) Uani 1 1 d . . . . .
F14 F 0.9629(8) 0.2470(2) 1.3285(9) 0.067(2) Uani 1 1 d . . . . .
F15 F 0.9946(7) 0.2648(2) 1.1218(9) 0.066(2) Uani 1 1 d . . . . .
C101 C 0.547(2) 0.3343(10) 1.285(3) 0.067(10) Uani 0.5 1 d . . P . .
H10B H 0.5145 0.3515 1.2273 0.101 Uiso 0.5 1 calc R U P . .
H10C H 0.5598 0.3454 1.3699 0.101 Uiso 0.5 1 calc R U P . .
H10D H 0.5014 0.3140 1.2971 0.101 Uiso 0.5 1 calc R U P . .
C100 C 0.638(3) 0.3231(11) 1.232(6) 0.102(17) Uani 0.5 1 d . . P . .
H10E H 0.6563 0.2999 1.2694 0.122 Uiso 0.5 1 calc R U P . .
H10F H 0.6925 0.3400 1.2562 0.122 Uiso 0.5 1 calc R U P . .
O100 O 0.6364(18) 0.3197(6) 1.083(3) 0.088(9) Uani 0.5 1 d . . P . .
H100 H 0.6826 0.3323 1.0509 0.131 Uiso 0.5 1 calc R U P . .
C201 C 0.6197(17) 0.3379(8) 1.745(4) 0.059(7) Uani 0.5 1 d . . P . .
H20A H 0.5744 0.3226 1.7961 0.088 Uiso 0.5 1 calc R U P . .
H20B H 0.6313 0.3599 1.7931 0.088 Uiso 0.5 1 calc R U P . .
H20C H 0.6849 0.3259 1.7314 0.088 Uiso 0.5 1 calc R U P . .
C200 C 0.576(3) 0.3452(11) 1.628(5) 0.088(12) Uani 0.5 1 d . U P . .
H20D H 0.6309 0.3554 1.5744 0.106 Uiso 0.5 1 calc R U P . .
H20E H 0.5278 0.3649 1.6455 0.106 Uiso 0.5 1 calc R U P . .
O200 O 0.5233(17) 0.3229(6) 1.545(3) 0.081(8) Uani 0.5 1 d . . P . .
H200 H 0.5355 0.3285 1.4679 0.122 Uiso 0.5 1 calc R U P . .


_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 C17 2.027(9) . ?
Ir1 N3 2.043(9) . ?
Ir1 C40 2.052(9) . ?
Ir1 N4 2.078(8) . ?
Ir1 N1 2.125(8) . ?
Ir1 N2 2.152(7) . ?
N1 C5 1.348(14) . ?
N1 C1 1.360(13) . ?
N2 C6 1.338(13) . ?
N2 C10 1.345(13) . ?
C1 C2 1.376(16) . ?
C1 H1A 0.9500 . ?
C2 C3 1.370(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.407(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.364(16) . ?
C4 H4A 0.9500 . ?
C5 C6 1.490(14) . ?
C6 C7 1.407(15) . ?
C7 C8 1.371(18) . ?
C7 H7A 0.9500 . ?
C8 C9 1.400(17) . ?
C8 H8A 0.9500 . ?
C9 C10 1.365(15) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
N3 C11 1.317(14) . ?
N3 C15 1.368(15) . ?
C11 C12 1.418(15) . ?
C11 H11A 0.9500 . ?
C12 C13 1.371(16) . ?
C12 H12A 0.9500 . ?
C13 C14 1.344(18) . ?
C13 H13A 0.9500 . ?
C14 C15 1.408(17) . ?
C14 H14A 0.9500 . ?
C15 C16 1.458(14) . ?
C16 C21 1.376(18) . ?
C16 C17 1.447(16) . ?
C17 C18 1.406(14) . ?
C18 C19 1.395(14) . ?
C18 C22 1.504(14) . ?
C19 C20 1.426(14) . ?
C19 H19A 0.9500 . ?
C20 C21 1.407(16) . ?
C20 C28 1.462(14) . ?
C21 H21A 0.9500 . ?
C22 C23 1.378(14) . ?
C22 C27 1.397(14) . ?
C23 C24 1.392(15) . ?
C23 H23A 0.9500 . ?
C24 C25 1.385(16) . ?
C24 H24A 0.9500 . ?
C25 C26 1.369(15) . ?
C25 H25A 0.9500 . ?
C26 C27 1.360(13) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 C33 1.398(15) . ?
C28 C29 1.399(15) . ?
C29 C30 1.374(17) . ?
C29 H29A 0.9500 . ?
C30 C31 1.35(2) . ?
C30 H30A 0.9500 . ?
C31 C32 1.377(17) . ?
C31 H31A 0.9500 . ?
C32 C33 1.364(17) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
N4 C34 1.332(13) . ?
N4 C38 1.359(13) . ?
C34 C35 1.375(16) . ?
C34 H34A 0.9500 . ?
C35 C36 1.389(16) . ?
C35 H35A 0.9500 . ?
C36 C37 1.383(15) . ?
C36 H36A 0.9500 . ?
C37 C38 1.373(15) . ?
C37 H37A 0.9500 . ?
C38 C39 1.468(14) . ?
C39 C44 1.401(15) . ?
C39 C40 1.445(13) . ?
C40 C41 1.372(13) . ?
C41 C42 1.406(14) . ?
C41 C45 1.490(13) . ?
C42 C43 1.397(14) . ?
C42 H42A 0.9500 . ?
C43 C44 1.373(14) . ?
C43 C51 1.501(13) . ?
C44 H44A 0.9500 . ?
C45 C50 1.385(15) . ?
C45 C46 1.401(14) . ?
C46 C47 1.386(15) . ?
C46 H46A 0.9500 . ?
C47 C48 1.391(19) . ?
C47 H47A 0.9500 . ?
C48 C49 1.372(19) . ?
C48 H48A 0.9500 . ?
C49 C50 1.370(17) . ?
C49 H49A 0.9500 . ?
C50 H50A 0.9500 . ?
C51 C56 1.378(15) . ?
C51 C52 1.390(14) . ?
C52 C53 1.381(19) . ?
C52 H52A 0.9500 . ?
C53 C54 1.41(2) . ?
C53 H53A 0.9500 . ?
C54 C55 1.343(19) . ?
C54 H54A 0.9500 . ?
C55 C56 1.398(18) . ?
C55 H55A 0.9500 . ?
C56 H56A 0.9500 . ?
P1 F11 1.572(7) . ?
P1 F15 1.580(9) . ?
P1 F12 1.583(9) . ?
P1 F13 1.596(7) . ?
P1 F10 1.606(9) . ?
P1 F14 1.614(9) . ?
C101 C100 1.39(5) . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C101 H10D 0.9800 . ?
C100 O100 1.53(6) . ?
C100 H10E 0.9900 . ?
C100 H10F 0.9900 . ?
O100 H100 0.8400 . ?
C201 C200 1.37(6) . ?
C201 H20A 0.9800 . ?
C201 H20B 0.9800 . ?
C201 H20C 0.9800 . ?
C200 O200 1.38(5) . ?
C200 H20D 0.9900 . ?
C200 H20E 0.9900 . ?
O200 H200 0.8400 . ?

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
C17 Ir1 N3 80.9(3) . . ?
C17 Ir1 C40 94.5(3) . . ?
N3 Ir1 C40 102.4(3) . . ?
C17 Ir1 N4 97.7(3) . . ?
N3 Ir1 N4 175.9(3) . . ?
C40 Ir1 N4 81.5(3) . . ?
C17 Ir1 N1 170.9(4) . . ?
N3 Ir1 N1 95.8(3) . . ?
C40 Ir1 N1 94.5(3) . . ?
N4 Ir1 N1 84.9(3) . . ?
C17 Ir1 N2 94.4(3) . . ?
N3 Ir1 N2 84.3(3) . . ?
C40 Ir1 N2 169.6(3) . . ?
N4 Ir1 N2 92.0(3) . . ?
N1 Ir1 N2 76.7(3) . . ?
C5 N1 C1 117.8(9) . . ?
C5 N1 Ir1 117.0(7) . . ?
C1 N1 Ir1 125.1(7) . . ?
C6 N2 C10 118.9(8) . . ?
C6 N2 Ir1 114.8(7) . . ?
C10 N2 Ir1 126.3(7) . . ?
N1 C1 C2 122.4(11) . . ?
N1 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C3 C2 C1 119.0(12) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 119.4(11) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 118.4(11) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
N1 C5 C4 123.0(10) . . ?
N1 C5 C6 114.2(9) . . ?
C4 C5 C6 122.8(10) . . ?
N2 C6 C7 121.3(10) . . ?
N2 C6 C5 117.2(9) . . ?
C7 C6 C5 121.5(10) . . ?
C8 C7 C6 119.2(11) . . ?
C8 C7 H7A 120.4 . . ?
C6 C7 H7A 120.4 . . ?
C7 C8 C9 118.7(10) . . ?
C7 C8 H8A 120.7 . . ?
C9 C8 H8A 120.7 . . ?
C10 C9 C8 119.0(10) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
N2 C10 C9 122.7(10) . . ?
N2 C10 H10A 118.6 . . ?
C9 C10 H10A 118.6 . . ?
C11 N3 C15 119.6(10) . . ?
C11 N3 Ir1 125.3(7) . . ?
C15 N3 Ir1 114.6(8) . . ?
N3 C11 C12 122.5(10) . . ?
N3 C11 H11A 118.8 . . ?
C12 C11 H11A 118.8 . . ?
C13 C12 C11 117.0(10) . . ?
C13 C12 H12A 121.5 . . ?
C11 C12 H12A 121.5 . . ?
C14 C13 C12 121.5(11) . . ?
C14 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C13 C14 C15 119.5(12) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
N3 C15 C14 119.8(13) . . ?
N3 C15 C16 114.0(12) . . ?
C14 C15 C16 126.1(13) . . ?
C21 C16 C17 121.9(13) . . ?
C21 C16 C15 122.3(13) . . ?
C17 C16 C15 115.6(12) . . ?
C18 C17 C16 116.2(10) . . ?
C18 C17 Ir1 132.9(7) . . ?
C16 C17 Ir1 110.7(8) . . ?
C19 C18 C17 121.1(9) . . ?
C19 C18 C22 114.2(9) . . ?
C17 C18 C22 124.6(9) . . ?
C18 C19 C20 121.8(9) . . ?
C18 C19 H19A 119.1 . . ?
C20 C19 H19A 119.1 . . ?
C21 C20 C19 116.9(9) . . ?
C21 C20 C28 123.4(9) . . ?
C19 C20 C28 119.6(9) . . ?
C16 C21 C20 121.4(12) . . ?
C16 C21 H21A 119.3 . . ?
C20 C21 H21A 119.3 . . ?
C23 C22 C27 119.1(9) . . ?
C23 C22 C18 120.4(9) . . ?
C27 C22 C18 120.3(9) . . ?
C22 C23 C24 119.9(10) . . ?
C22 C23 H23A 120.1 . . ?
C24 C23 H23A 120.1 . . ?
C25 C24 C23 121.2(10) . . ?
C25 C24 H24A 119.4 . . ?
C23 C24 H24A 119.4 . . ?
C26 C25 C24 117.2(9) . . ?
C26 C25 H25A 121.4 . . ?
C24 C25 H25A 121.4 . . ?
C27 C26 C25 123.2(10) . . ?
C27 C26 H26A 118.4 . . ?
C25 C26 H26A 118.4 . . ?
C26 C27 C22 119.2(10) . . ?
C26 C27 H27A 120.4 . . ?
C22 C27 H27A 120.4 . . ?
C33 C28 C29 116.6(10) . . ?
C33 C28 C20 121.8(10) . . ?
C29 C28 C20 121.5(10) . . ?
C30 C29 C28 121.1(11) . . ?
C30 C29 H29A 119.5 . . ?
C28 C29 H29A 119.5 . . ?
C31 C30 C29 120.7(12) . . ?
C31 C30 H30A 119.6 . . ?
C29 C30 H30A 119.6 . . ?
C30 C31 C32 119.9(12) . . ?
C30 C31 H31A 120.1 . . ?
C32 C31 H31A 120.1 . . ?
C33 C32 C31 120.1(13) . . ?
C33 C32 H32A 119.9 . . ?
C31 C32 H32A 119.9 . . ?
C32 C33 C28 121.6(11) . . ?
C32 C33 H33A 119.2 . . ?
C28 C33 H33A 119.2 . . ?
C34 N4 C38 120.9(9) . . ?
C34 N4 Ir1 124.0(7) . . ?
C38 N4 Ir1 114.8(6) . . ?
N4 C34 C35 122.0(10) . . ?
N4 C34 H34A 119.0 . . ?
C35 C34 H34A 119.0 . . ?
C34 C35 C36 118.3(10) . . ?
C34 C35 H35A 120.8 . . ?
C36 C35 H35A 120.8 . . ?
C37 C36 C35 119.0(10) . . ?
C37 C36 H36A 120.5 . . ?
C35 C36 H36A 120.5 . . ?
C38 C37 C36 120.8(10) . . ?
C38 C37 H37A 119.6 . . ?
C36 C37 H37A 119.6 . . ?
N4 C38 C37 119.1(9) . . ?
N4 C38 C39 114.0(9) . . ?
C37 C38 C39 126.8(9) . . ?
C44 C39 C40 121.8(9) . . ?
C44 C39 C38 120.4(9) . . ?
C40 C39 C38 117.7(9) . . ?
C41 C40 C39 116.7(8) . . ?
C41 C40 Ir1 132.5(7) . . ?
C39 C40 Ir1 110.6(6) . . ?
C40 C41 C42 120.7(9) . . ?
C40 C41 C45 125.5(9) . . ?
C42 C41 C45 113.8(8) . . ?
C43 C42 C41 122.0(9) . . ?
C43 C42 H42A 119.0 . . ?
C41 C42 H42A 119.0 . . ?
C44 C43 C42 118.6(9) . . ?
C44 C43 C51 120.2(8) . . ?
C42 C43 C51 121.0(8) . . ?
C43 C44 C39 120.0(9) . . ?
C43 C44 H44A 120.0 . . ?
C39 C44 H44A 120.0 . . ?
C50 C45 C46 118.4(10) . . ?
C50 C45 C41 121.3(10) . . ?
C46 C45 C41 120.1(9) . . ?
C47 C46 C45 119.9(10) . . ?
C47 C46 H46A 120.1 . . ?
C45 C46 H46A 120.1 . . ?
C46 C47 C48 120.5(11) . . ?
C46 C47 H47A 119.7 . . ?
C48 C47 H47A 119.7 . . ?
C49 C48 C47 119.2(11) . . ?
C49 C48 H48A 120.4 . . ?
C47 C48 H48A 120.4 . . ?
C50 C49 C48 120.6(12) . . ?
C50 C49 H49A 119.7 . . ?
C48 C49 H49A 119.7 . . ?
C49 C50 C45 121.4(11) . . ?
C49 C50 H50A 119.3 . . ?
C45 C50 H50A 119.3 . . ?
C56 C51 C52 118.3(9) . . ?
C56 C51 C43 120.2(8) . . ?
C52 C51 C43 121.5(9) . . ?
C53 C52 C51 121.2(12) . . ?
C53 C52 H52A 119.4 . . ?
C51 C52 H52A 119.4 . . ?
C52 C53 C54 119.5(12) . . ?
C52 C53 H53A 120.2 . . ?
C54 C53 H53A 120.2 . . ?
C55 C54 C53 119.2(10) . . ?
C55 C54 H54A 120.4 . . ?
C53 C54 H54A 120.4 . . ?
C54 C55 C56 121.3(11) . . ?
C54 C55 H55A 119.3 . . ?
C56 C55 H55A 119.3 . . ?
C51 C56 C55 120.4(10) . . ?
C51 C56 H56A 119.8 . . ?
C55 C56 H56A 119.8 . . ?
F11 P1 F15 90.8(5) . . ?
F11 P1 F12 92.0(4) . . ?
F15 P1 F12 91.3(6) . . ?
F11 P1 F13 177.8(5) . . ?
F15 P1 F13 91.0(5) . . ?
F12 P1 F13 89.2(4) . . ?
F11 P1 F10 89.4(4) . . ?
F15 P1 F10 178.8(6) . . ?
F12 P1 F10 89.8(6) . . ?
F13 P1 F10 88.8(5) . . ?
F11 P1 F14 88.0(5) . . ?
F15 P1 F14 90.6(5) . . ?
F12 P1 F14 178.1(6) . . ?
F13 P1 F14 90.7(5) . . ?
F10 P1 F14 88.3(6) . . ?
C100 C101 H10B 109.5 . . ?
C100 C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
C100 C101 H10D 109.5 . . ?
H10B C101 H10D 109.5 . . ?
H10C C101 H10D 109.5 . . ?
C101 C100 O100 114(3) . . ?
C101 C100 H10E 108.7 . . ?
O100 C100 H10E 108.7 . . ?
C101 C100 H10F 108.7 . . ?
O100 C100 H10F 108.7 . . ?
H10E C100 H10F 107.6 . . ?
C100 O100 H100 109.5 . . ?
C200 C201 H20A 109.5 . . ?
C200 C201 H20B 109.5 . . ?
H20A C201 H20B 109.5 . . ?
C200 C201 H20C 109.5 . . ?
H20A C201 H20C 109.5 . . ?
H20B C201 H20C 109.5 . . ?
C201 C200 O200 129(4) . . ?
C201 C200 H20D 105.1 . . ?
O200 C200 H20D 105.1 . . ?
C201 C200 H20E 105.1 . . ?
O200 C200 H20E 105.1 . . ?
H20D C200 H20E 105.9 . . ?
C200 O200 H200 109.5 . . ?

_refine_diff_density_max         4.806
_refine_diff_density_min         -1.207
_refine_diff_density_rms         0.152

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_3s
_database_code_depnum_ccdc_archive 'CCDC 1019228'
_audit_update_record             
;
2014-08-13 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H32 Ir N4, F6 P'
_chemical_formula_sum            'C44 H32 F6 Ir N4 P'
_chemical_formula_weight         953.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 '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                   15.0877(10)
_cell_length_b                   13.1747(9)
_cell_length_c                   18.0930(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.094(2)
_cell_angle_gamma                90
_cell_volume                     3576.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9416
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      67.67

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             1880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    8.270
_shelx_estimated_absorpt_T_min   0.318
_shelx_estimated_absorpt_T_max   0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_T_max  0.718
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            63369
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.630
_diffrn_reflns_theta_max         68.277
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6470
_reflns_number_gt                6256
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0295P)²+2.9340P] 
 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         6470
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0492
_refine_ls_wR_factor_gt          0.0487
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_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 0.27514(2) 0.38108(2) 0.11354(2) 0.01406(4) Uani 1 1 d . . . . .
N1 N 0.37126(12) 0.26206(13) 0.11091(10) 0.0175(4) Uani 1 1 d . . . . .
N2 N 0.19597(12) 0.25147(13) 0.07997(9) 0.0168(3) Uani 1 1 d . . . . .
C1 C 0.45974(15) 0.27324(18) 0.12695(13) 0.0220(4) Uani 1 1 d . . . . .
H1A H 0.4819 0.3351 0.1487 0.026 Uiso 1 1 calc R U . . .
C2 C 0.52005(15) 0.19768(18) 0.11292(13) 0.0250(5) Uani 1 1 d . . . . .
H2A H 0.5823 0.2076 0.1249 0.030 Uiso 1 1 calc R U . . .
C3 C 0.48777(16) 0.10796(18) 0.08125(14) 0.0251(5) Uani 1 1 d . . . . .
H3A H 0.5277 0.0560 0.0697 0.030 Uiso 1 1 calc R U . . .
C4 C 0.39664(15) 0.09444(18) 0.06649(12) 0.0216(4) Uani 1 1 d . . . . .
H4A H 0.3734 0.0325 0.0456 0.026 Uiso 1 1 calc R U . . .
C5 C 0.33939(14) 0.17245(16) 0.08250(11) 0.0169(4) Uani 1 1 d . . . . .
C6 C 0.24125(14) 0.16410(16) 0.07189(11) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.19696(15) 0.07229(17) 0.05743(13) 0.0225(5) Uani 1 1 d . . . . .
H7A H 0.2296 0.0119 0.0509 0.027 Uiso 1 1 calc R U . . .
C8 C 0.10554(16) 0.07015(18) 0.05267(13) 0.0251(5) Uani 1 1 d . . . . .
H8A H 0.0745 0.0080 0.0431 0.030 Uiso 1 1 calc R U . . .
C9 C 0.05881(15) 0.15907(19) 0.06189(13) 0.0238(5) Uani 1 1 d . . . . .
H9A H -0.0044 0.1588 0.0594 0.029 Uiso 1 1 calc R U . . .
C10 C 0.10652(14) 0.24823(17) 0.07487(12) 0.0205(4) Uani 1 1 d . . . . .
H10A H 0.0748 0.3095 0.0804 0.025 Uiso 1 1 calc R U . . .
N3 N 0.30531(11) 0.42634(13) 0.01063(10) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.27227(16) 0.38407(16) -0.05452(13) 0.0205(5) Uani 1 1 d . . . . .
H11A H 0.2341 0.3268 -0.0537 0.025 Uiso 1 1 calc R U . . .
C12 C 0.29193(16) 0.42097(18) -0.12223(12) 0.0242(5) Uani 1 1 d . . . . .
H12A H 0.2682 0.3893 -0.1672 0.029 Uiso 1 1 calc R U . . .
C13 C 0.34682(17) 0.50492(19) -0.12360(13) 0.0274(5) Uani 1 1 d . . . . .
H13A H 0.3614 0.5317 -0.1695 0.033 Uiso 1 1 calc R U . . .
C14 C 0.38011(16) 0.54919(18) -0.05724(13) 0.0243(5) Uani 1 1 d . . . . .
H14A H 0.4175 0.6072 -0.0575 0.029 Uiso 1 1 calc R U . . .
C15 C 0.35916(14) 0.50941(16) 0.00992(12) 0.0179(4) Uani 1 1 d . . . . .
C16 C 0.39152(13) 0.54845(16) 0.08376(12) 0.0173(4) Uani 1 1 d . . . . .
C17 C 0.36097(14) 0.49397(16) 0.14388(12) 0.0179(4) Uani 1 1 d . . . . .
C18 C 0.39594(15) 0.52479(18) 0.21486(12) 0.0237(5) Uani 1 1 d . . . . .
H18A H 0.3787 0.4894 0.2568 0.028 Uiso 1 1 calc R U . . .
C19 C 0.45521(17) 0.60568(18) 0.22621(13) 0.0247(5) Uani 1 1 d . . . . .
H19A H 0.4786 0.6228 0.2755 0.030 Uiso 1 1 calc R U . . .
C20 C 0.48127(14) 0.66265(16) 0.16648(12) 0.0198(4) Uani 1 1 d . . . . .
C21 C 0.44841(15) 0.63121(16) 0.09511(13) 0.0193(4) Uani 1 1 d . . . . .
H21A H 0.4653 0.6672 0.0533 0.023 Uiso 1 1 calc R U . . .
C22 C 0.53897(14) 0.75402(16) 0.17890(12) 0.0200(4) Uani 1 1 d . . . . .
C23 C 0.58153(15) 0.79762(17) 0.12153(13) 0.0233(5) Uani 1 1 d . . . . .
H23A H 0.5754 0.7666 0.0739 0.028 Uiso 1 1 calc R U . . .
C24 C 0.63227(17) 0.88486(17) 0.13274(15) 0.0267(5) Uani 1 1 d . . . . .
H24A H 0.6608 0.9124 0.0929 0.032 Uiso 1 1 calc R U . . .
C25 C 0.64181(15) 0.93248(17) 0.20161(13) 0.0243(5) Uani 1 1 d . . . . .
H25A H 0.6753 0.9934 0.2088 0.029 Uiso 1 1 calc R U . . .
C26 C 0.60187(18) 0.88982(18) 0.25939(15) 0.0282(5) Uani 1 1 d . . . . .
H26A H 0.6091 0.9207 0.3071 0.034 Uiso 1 1 calc R U . . .
C27 C 0.55121(16) 0.80216(19) 0.24827(13) 0.0267(5) Uani 1 1 d . . . . .
H27A H 0.5241 0.7741 0.2887 0.032 Uiso 1 1 calc R U . . .
N4 N 0.24039(12) 0.35644(14) 0.21823(10) 0.0170(4) Uani 1 1 d . . . . .
C28 C 0.27501(14) 0.28367(17) 0.26519(12) 0.0207(4) Uani 1 1 d . . . . .
H28A H 0.3203 0.2409 0.2498 0.025 Uiso 1 1 calc R U . . .
C29 C 0.24731(15) 0.26886(18) 0.33459(13) 0.0241(5) Uani 1 1 d . . . . .
H29A H 0.2734 0.2173 0.3665 0.029 Uiso 1 1 calc R U . . .
C30 C 0.18056(15) 0.33078(18) 0.35690(12) 0.0236(5) Uani 1 1 d . . . . .
H30A H 0.1603 0.3225 0.4045 0.028 Uiso 1 1 calc R U . . .
C31 C 0.14416(15) 0.40457(17) 0.30880(12) 0.0209(4) Uani 1 1 d . . . . .
H31A H 0.0981 0.4471 0.3232 0.025 Uiso 1 1 calc R U . . .
C32 C 0.17432(14) 0.41719(16) 0.23952(12) 0.0178(4) Uani 1 1 d . . . . .
C33 C 0.13975(14) 0.49087(16) 0.18294(11) 0.0166(4) Uani 1 1 d . . . . .
C34 C 0.17690(13) 0.48402(16) 0.11458(12) 0.0164(4) Uani 1 1 d . . . . .
C35 C 0.14285(14) 0.55047(16) 0.05804(11) 0.0184(4) Uani 1 1 d . . . . .
H35A H 0.1640 0.5460 0.0105 0.022 Uiso 1 1 calc R U . . .
C36 C 0.07925(16) 0.62229(16) 0.06982(13) 0.0193(5) Uani 1 1 d . . . . .
H36A H 0.0577 0.6660 0.0302 0.023 Uiso 1 1 calc R U . . .
C37 C 0.04560(15) 0.63228(16) 0.13906(13) 0.0182(4) Uani 1 1 d . . . . .
C38 C 0.07543(14) 0.56355(16) 0.19506(11) 0.0173(4) Uani 1 1 d . . . . .
H38A H 0.0518 0.5662 0.2417 0.021 Uiso 1 1 calc R U . . .
C39 C -0.01527(14) 0.71638(17) 0.15341(11) 0.0185(4) Uani 1 1 d . . . . .
C40 C 0.00059(15) 0.81432(18) 0.12730(13) 0.0240(5) Uani 1 1 d . . . . .
H40A H 0.0500 0.8259 0.0999 0.029 Uiso 1 1 calc R U . . .
C41 C -0.05492(17) 0.89405(18) 0.14096(15) 0.0269(5) Uani 1 1 d . . . . .
H41A H -0.0433 0.9599 0.1230 0.032 Uiso 1 1 calc R U . . .
C42 C -0.12731(17) 0.87873(17) 0.18061(14) 0.0238(5) Uani 1 1 d . . . . .
H42A H -0.1657 0.9336 0.1891 0.029 Uiso 1 1 calc R U . . .
C43 C -0.14350(15) 0.78311(18) 0.20777(13) 0.0239(5) Uani 1 1 d . . . . .
H43A H -0.1927 0.7724 0.2355 0.029 Uiso 1 1 calc R U . . .
C44 C -0.08755(15) 0.70265(17) 0.19439(12) 0.0216(4) Uani 1 1 d . . . . .
H44A H -0.0988 0.6373 0.2135 0.026 Uiso 1 1 calc R U . . .
P1 P 0.71459(4) 0.68420(4) 0.42732(3) 0.02074(12) Uani 1 1 d . . . . .
F10 F 0.76005(10) 0.71715(15) 0.35559(9) 0.0446(4) Uani 1 1 d . . . . .
F11 F 0.78541(12) 0.59344(14) 0.44260(11) 0.0477(4) Uani 1 1 d . . . . .
F12 F 0.78029(12) 0.75654(13) 0.47777(9) 0.0460(4) Uani 1 1 d . . . . .
F13 F 0.64408(10) 0.77441(11) 0.41433(8) 0.0339(3) Uani 1 1 d . . . . .
F14 F 0.64814(12) 0.61201(13) 0.37795(11) 0.0478(4) Uani 1 1 d . . . . .
F15 F 0.66888(10) 0.65059(11) 0.50006(8) 0.0322(3) 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 C17 2.010(2) . ?
Ir1 C34 2.011(2) . ?
Ir1 N4 2.0442(18) . ?
Ir1 N3 2.0517(17) . ?
Ir1 N2 2.1349(18) . ?
Ir1 N1 2.1399(18) . ?
N1 C1 1.344(3) . ?
N1 C5 1.355(3) . ?
N2 C10 1.343(3) . ?
N2 C6 1.354(3) . ?
C1 C2 1.390(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.380(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.477(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.373(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.386(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
N3 C11 1.350(3) . ?
N3 C15 1.364(3) . ?
C11 C12 1.379(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.466(3) . ?
C16 C21 1.389(3) . ?
C16 C17 1.420(3) . ?
C17 C18 1.396(3) . ?
C18 C19 1.392(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.406(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.396(3) . ?
C20 C22 1.489(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.400(3) . ?
C22 C27 1.401(3) . ?
C23 C24 1.384(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.389(4) . ?
C24 H24A 0.9500 . ?
C25 C26 1.380(4) . ?
C25 H25A 0.9500 . ?
C26 C27 1.388(3) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
N4 C28 1.349(3) . ?
N4 C32 1.365(3) . ?
C28 C29 1.379(3) . ?
C28 H28A 0.9500 . ?
C29 C30 1.389(3) . ?
C29 H29A 0.9500 . ?
C30 C31 1.379(3) . ?
C30 H30A 0.9500 . ?
C31 C32 1.388(3) . ?
C31 H31A 0.9500 . ?
C32 C33 1.466(3) . ?
C33 C38 1.397(3) . ?
C33 C34 1.414(3) . ?
C34 C35 1.402(3) . ?
C35 C36 1.380(3) . ?
C35 H35A 0.9500 . ?
C36 C37 1.407(3) . ?
C36 H36A 0.9500 . ?
C37 C38 1.397(3) . ?
C37 C39 1.480(3) . ?
C38 H38A 0.9500 . ?
C39 C44 1.394(3) . ?
C39 C40 1.403(3) . ?
C40 C41 1.382(3) . ?
C40 H40A 0.9500 . ?
C41 C42 1.384(4) . ?
C41 H41A 0.9500 . ?
C42 C43 1.383(3) . ?
C42 H42A 0.9500 . ?
C43 C44 1.392(3) . ?
C43 H43A 0.9500 . ?
C44 H44A 0.9500 . ?
P1 F14 1.5866(16) . ?
P1 F10 1.5912(15) . ?
P1 F12 1.5913(16) . ?
P1 F13 1.5957(15) . ?
P1 F11 1.6079(16) . ?
P1 F15 1.6114(14) . ?

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
C17 Ir1 C34 87.28(8) . . ?
C17 Ir1 N4 94.91(8) . . ?
C34 Ir1 N4 80.60(8) . . ?
C17 Ir1 N3 80.46(8) . . ?
C34 Ir1 N3 92.71(8) . . ?
N4 Ir1 N3 172.08(7) . . ?
C17 Ir1 N2 173.96(7) . . ?
C34 Ir1 N2 98.71(7) . . ?
N4 Ir1 N2 86.89(7) . . ?
N3 Ir1 N2 98.37(7) . . ?
C17 Ir1 N1 97.46(8) . . ?
C34 Ir1 N1 175.22(7) . . ?
N4 Ir1 N1 98.36(7) . . ?
N3 Ir1 N1 88.66(7) . . ?
N2 Ir1 N1 76.56(7) . . ?
C1 N1 C5 118.80(19) . . ?
C1 N1 Ir1 125.09(15) . . ?
C5 N1 Ir1 115.65(14) . . ?
C10 N2 C6 118.70(18) . . ?
C10 N2 Ir1 124.93(15) . . ?
C6 N2 Ir1 115.92(14) . . ?
N1 C1 C2 122.4(2) . . ?
N1 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
N1 C5 C4 121.26(19) . . ?
N1 C5 C6 115.13(18) . . ?
C4 C5 C6 123.6(2) . . ?
N2 C6 C7 121.38(19) . . ?
N2 C6 C5 115.66(18) . . ?
C7 C6 C5 122.9(2) . . ?
C8 C7 C6 119.2(2) . . ?
C8 C7 H7A 120.4 . . ?
C6 C7 H7A 120.4 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 H9A 120.8 . . ?
C8 C9 H9A 120.8 . . ?
N2 C10 C9 122.6(2) . . ?
N2 C10 H10A 118.7 . . ?
C9 C10 H10A 118.7 . . ?
C11 N3 C15 119.19(18) . . ?
C11 N3 Ir1 125.14(15) . . ?
C15 N3 Ir1 115.57(14) . . ?
N3 C11 C12 122.4(2) . . ?
N3 C11 H11A 118.8 . . ?
C12 C11 H11A 118.8 . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
C14 C13 C12 119.0(2) . . ?
C14 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
N3 C15 C14 120.1(2) . . ?
N3 C15 C16 114.45(18) . . ?
C14 C15 C16 125.4(2) . . ?
C21 C16 C17 121.9(2) . . ?
C21 C16 C15 123.42(19) . . ?
C17 C16 C15 114.64(19) . . ?
C18 C17 C16 115.84(19) . . ?
C18 C17 Ir1 129.51(16) . . ?
C16 C17 Ir1 114.63(15) . . ?
C19 C18 C17 122.2(2) . . ?
C19 C18 H18A 118.9 . . ?
C17 C18 H18A 118.9 . . ?
C18 C19 C20 121.5(2) . . ?
C18 C19 H19A 119.2 . . ?
C20 C19 H19A 119.2 . . ?
C21 C20 C19 116.9(2) . . ?
C21 C20 C22 121.6(2) . . ?
C19 C20 C22 121.5(2) . . ?
C16 C21 C20 121.5(2) . . ?
C16 C21 H21A 119.2 . . ?
C20 C21 H21A 119.2 . . ?
C23 C22 C27 116.8(2) . . ?
C23 C22 C20 121.8(2) . . ?
C27 C22 C20 121.4(2) . . ?
C24 C23 C22 121.5(2) . . ?
C24 C23 H23A 119.3 . . ?
C22 C23 H23A 119.3 . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 H24A 119.7 . . ?
C25 C24 H24A 119.7 . . ?
C26 C25 C24 118.9(2) . . ?
C26 C25 H25A 120.5 . . ?
C24 C25 H25A 120.5 . . ?
C25 C26 C27 120.5(2) . . ?
C25 C26 H26A 119.8 . . ?
C27 C26 H26A 119.8 . . ?
C26 C27 C22 121.7(2) . . ?
C26 C27 H27A 119.2 . . ?
C22 C27 H27A 119.2 . . ?
C28 N4 C32 118.97(19) . . ?
C28 N4 Ir1 125.19(15) . . ?
C32 N4 Ir1 115.79(14) . . ?
N4 C28 C29 122.7(2) . . ?
N4 C28 H28A 118.7 . . ?
C29 C28 H28A 118.7 . . ?
C28 C29 C30 118.7(2) . . ?
C28 C29 H29A 120.6 . . ?
C30 C29 H29A 120.6 . . ?
C31 C30 C29 118.9(2) . . ?
C31 C30 H30A 120.6 . . ?
C29 C30 H30A 120.6 . . ?
C30 C31 C32 120.5(2) . . ?
C30 C31 H31A 119.8 . . ?
C32 C31 H31A 119.8 . . ?
N4 C32 C31 120.2(2) . . ?
N4 C32 C33 114.05(18) . . ?
C31 C32 C33 125.7(2) . . ?
C38 C33 C34 121.84(19) . . ?
C38 C33 C32 123.09(19) . . ?
C34 C33 C32 115.07(19) . . ?
C35 C34 C33 116.74(19) . . ?
C35 C34 Ir1 128.89(16) . . ?
C33 C34 Ir1 114.35(15) . . ?
C36 C35 C34 121.5(2) . . ?
C36 C35 H35A 119.3 . . ?
C34 C35 H35A 119.3 . . ?
C35 C36 C37 121.6(2) . . ?
C35 C36 H36A 119.2 . . ?
C37 C36 H36A 119.2 . . ?
C38 C37 C36 117.8(2) . . ?
C38 C37 C39 121.1(2) . . ?
C36 C37 C39 121.04(19) . . ?
C33 C38 C37 120.40(19) . . ?
C33 C38 H38A 119.8 . . ?
C37 C38 H38A 119.8 . . ?
C44 C39 C40 118.0(2) . . ?
C44 C39 C37 122.1(2) . . ?
C40 C39 C37 119.89(19) . . ?
C41 C40 C39 120.7(2) . . ?
C41 C40 H40A 119.7 . . ?
C39 C40 H40A 119.7 . . ?
C40 C41 C42 120.6(2) . . ?
C40 C41 H41A 119.7 . . ?
C42 C41 H41A 119.7 . . ?
C43 C42 C41 119.7(2) . . ?
C43 C42 H42A 120.1 . . ?
C41 C42 H42A 120.1 . . ?
C42 C43 C44 119.9(2) . . ?
C42 C43 H43A 120.1 . . ?
C44 C43 H43A 120.1 . . ?
C43 C44 C39 121.1(2) . . ?
C43 C44 H44A 119.4 . . ?
C39 C44 H44A 119.4 . . ?
F14 P1 F10 90.33(10) . . ?
F14 P1 F12 179.16(11) . . ?
F10 P1 F12 90.47(9) . . ?
F14 P1 F13 89.55(9) . . ?
F10 P1 F13 90.86(9) . . ?
F12 P1 F13 90.19(9) . . ?
F14 P1 F11 91.13(11) . . ?
F10 P1 F11 90.40(9) . . ?
F12 P1 F11 89.11(11) . . ?
F13 P1 F11 178.56(9) . . ?
F14 P1 F15 89.74(10) . . ?
F10 P1 F15 179.79(10) . . ?
F12 P1 F15 89.46(9) . . ?
F13 P1 F15 89.34(8) . . ?
F11 P1 F15 89.39(8) . . ?

_refine_diff_density_max         0.968
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_AB151_123K
_database_code_depnum_ccdc_archive 'CCDC 1019229'
_audit_update_record             
;
2014-08-13 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;
_audit_creation_date             2014-07-07
_audit_creation_method           CRYSTALS_ver_14.52

_oxford_structure_analysis_title 'ab151_123k_0m in P-1'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        A.Buenzli
#end of refcif 
_cell_length_a                   10.8073(6)
_cell_length_b                   13.5065(8)
_cell_length_c                   20.8777(12)
_cell_angle_alpha                80.953(3)
_cell_angle_beta                 86.577(3)
_cell_angle_gamma                78.797(3)
_cell_volume                     2950.90(17)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ir -4.7710 6.5667 27.3049 1.5928 16.7296 8.8655 15.6115 0.4179 5.8338 45.0011
11.4722 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C62 H44 F6 Ir1 N4 P1 
# Dc =      1.33 Fooo =   1380.00 Mu =     51.21 M =   1182.24
# Found Formula = C76 H60 F6 Ir1 N4 P1 
# Dc =      1.54 FOOO =   1380.00 Mu =     52.07 M =   1366.52

_chemical_formula_sum            'C76 H60 F6 Ir1 N4 P1'
_chemical_formula_moiety         'C76 H60 F6 Ir1 N4 P1'
_chemical_formula_weight         1366.52


_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      3
_cell_measurement_theta_max      68
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_max          0.080

_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1380
_exptl_absorpt_coefficient_mu    5.207

# Sheldrick geometric approximatio 0.81 0.81 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.81
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            50598
_reflns_number_total             10694
_diffrn_reflns_av_R_equivalents  0.037
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 10694 
# Theoretical number of reflections is about 21674 


_diffrn_reflns_theta_min         3.373
_diffrn_reflns_theta_max         68.371
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        68.370
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -12
_reflns_limit_h_max              13
_reflns_limit_k_min              -15
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.56
_refine_diff_density_max         0.96


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         10647
_refine_ls_number_restraints     0
_refine_ls_number_parameters     793
_oxford_refine_ls_R_factor_ref   0.0243
_refine_ls_wR_factor_ref         0.0492
_refine_ls_goodness_of_fit_ref   0.9016
_refine_ls_shift/su_max          0.0033877
_refine_ls_shift/su_mean         0.0000371


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        10648
_refine_ls_R_factor_all          0.0243
_refine_ls_wR_factor_all         0.0492

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9718
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_gt          0.0474

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 3.07 4.35 2.05 0.544 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Ir1 Ir 0.313766(8) 0.708245(7) 0.247768(4) 0.0086 1.0000 Uani . . . . . .
N2 N 0.29331(17) 0.83092(14) 0.17528(9) 0.0130 1.0000 Uani . . . . . .
C3 C 0.1898(2) 0.90435(16) 0.18096(10) 0.0134 1.0000 Uani . . . . . .
C4 C 0.1649(2) 0.98936(17) 0.13261(11) 0.0171 1.0000 Uani . . . . . .
C5 C 0.2448(2) 0.99792(18) 0.07873(11) 0.0194 1.0000 Uani . . . . . .
C6 C 0.3489(2) 0.92095(18) 0.07306(11) 0.0185 1.0000 Uani . . . . . .
C7 C 0.3693(2) 0.83803(17) 0.12212(11) 0.0160 1.0000 Uani . . . . . .
C8 C 0.1167(2) 0.88786(16) 0.24147(11) 0.0135 1.0000 Uani . . . . . .
C9 C 0.1663(2) 0.80038(16) 0.28631(10) 0.0129 1.0000 Uani . . . . . .
C10 C 0.1081(2) 0.79350(16) 0.34822(11) 0.0134 1.0000 Uani . . . . . .
C11 C 0.0011(2) 0.86503(17) 0.36218(11) 0.0153 1.0000 Uani . . . . . .
C12 C -0.0538(2) 0.94501(16) 0.31600(11) 0.0152 1.0000 Uani . . . . . .
C13 C 0.0070(2) 0.95682(17) 0.25534(11) 0.0147 1.0000 Uani . . . . . .
C14 C -0.1732(2) 1.01408(16) 0.33104(11) 0.0160 1.0000 Uani . . . . . .
C15 C -0.2622(2) 1.05466(18) 0.28313(13) 0.0208 1.0000 Uani . . . . . .
C16 C -0.3747(2) 1.11793(18) 0.29698(14) 0.0260 1.0000 Uani . . . . . .
C17 C -0.4019(2) 1.14114(19) 0.35930(14) 0.0280 1.0000 Uani . . . . . .
C18 C -0.3152(3) 1.10177(19) 0.40707(13) 0.0276 1.0000 Uani . . . . . .
C19 C -0.2018(2) 1.03876(18) 0.39332(12) 0.0227 1.0000 Uani . . . . . .
C20 C 0.1503(2) 0.71244(16) 0.40423(10) 0.0139 1.0000 Uani . . . . . .
C21 C 0.1171(2) 0.61683(17) 0.41038(12) 0.0184 1.0000 Uani . . . . . .
C22 C 0.1459(2) 0.54543(18) 0.46569(13) 0.0237 1.0000 Uani . . . . . .
C23 C 0.2085(2) 0.5694(2) 0.51577(12) 0.0248 1.0000 Uani . . . . . .
C24 C 0.2422(2) 0.6645(2) 0.51013(12) 0.0237 1.0000 Uani . . . . . .
C25 C 0.2133(2) 0.73494(18) 0.45495(11) 0.0190 1.0000 Uani . . . . . .
N26 N 0.45312(18) 0.60646(14) 0.19001(9) 0.0143 1.0000 Uani . . . . . .
C27 C 0.5781(2) 0.57310(17) 0.19750(11) 0.0176 1.0000 Uani . . . . . .
C28 C 0.6448(2) 0.49178(19) 0.16730(13) 0.0255 1.0000 Uani . . . . . .
C29 C 0.5832(3) 0.4441(2) 0.12973(15) 0.0327 1.0000 Uani . . . . . .
C30 C 0.4559(3) 0.4783(2) 0.12068(13) 0.0270 1.0000 Uani . . . . . .
C31 C 0.3934(2) 0.55952(17) 0.15085(11) 0.0186 1.0000 Uani . . . . . .
C32 C 0.2557(2) 0.59398(17) 0.14439(11) 0.0182 1.0000 Uani . . . . . .
N33 N 0.19693(18) 0.65214(14) 0.18767(9) 0.0158 1.0000 Uani . . . . . .
C34 C 0.0703(2) 0.68014(18) 0.18725(12) 0.0199 1.0000 Uani . . . . . .
C35 C -0.0025(2) 0.65323(18) 0.14296(13) 0.0232 1.0000 Uani . . . . . .
C36 C 0.0582(2) 0.59650(19) 0.09675(12) 0.0239 1.0000 Uani . . . . . .
C37 C 0.1874(2) 0.56566(19) 0.09721(12) 0.0234 1.0000 Uani . . . . . .
C38 C 0.6534(2) 0.62168(17) 0.23602(11) 0.0167 1.0000 Uani . . . . . .
C39 C 0.7396(2) 0.55887(18) 0.27929(12) 0.0202 1.0000 Uani . . . . . .
C40 C 0.8188(2) 0.6008(2) 0.31252(12) 0.0234 1.0000 Uani . . . . . .
C41 C 0.8138(2) 0.70562(19) 0.30265(12) 0.0219 1.0000 Uani . . . . . .
C42 C 0.7298(2) 0.76814(19) 0.25948(12) 0.0212 1.0000 Uani . . . . . .
C43 C 0.6500(2) 0.72662(18) 0.22602(11) 0.0178 1.0000 Uani . . . . . .
N44 N 0.34579(17) 0.57827(14) 0.31508(9) 0.0130 1.0000 Uani . . . . . .
C45 C 0.4305(2) 0.57643(16) 0.36060(10) 0.0132 1.0000 Uani . . . . . .
C46 C 0.4681(2) 0.67444(16) 0.36141(10) 0.0118 1.0000 Uani . . . . . .
C47 C 0.41690(19) 0.75514(16) 0.31243(10) 0.0113 1.0000 Uani . . . . . .
C48 C 0.4359(2) 0.85328(16) 0.32028(10) 0.0130 1.0000 Uani . . . . . .
C49 C 0.3815(2) 0.95189(16) 0.27898(11) 0.0138 1.0000 Uani . . . . . .
C50 C 0.2770(2) 1.01544(17) 0.30254(11) 0.0166 1.0000 Uani . . . . . .
C51 C 0.2314(2) 1.11209(18) 0.26904(12) 0.0207 1.0000 Uani . . . . . .
C52 C 0.2893(2) 1.14587(18) 0.21121(12) 0.0225 1.0000 Uani . . . . . .
C53 C 0.3929(2) 1.08361(18) 0.18685(12) 0.0209 1.0000 Uani . . . . . .
C54 C 0.4393(2) 0.98738(17) 0.22059(11) 0.0173 1.0000 Uani . . . . . .
C55 C 0.5106(2) 0.86502(16) 0.37028(11) 0.0140 1.0000 Uani . . . . . .
C56 C 0.5697(2) 0.78265(16) 0.41382(10) 0.0138 1.0000 Uani . . . . . .
C57 C 0.5453(2) 0.68710(16) 0.40957(10) 0.0134 1.0000 Uani . . . . . .
C58 C 0.6551(2) 0.79734(16) 0.46325(10) 0.0136 1.0000 Uani . . . . . .
C59 C 0.7724(2) 0.73312(17) 0.47382(11) 0.0167 1.0000 Uani . . . . . .
C60 C 0.8525(2) 0.74839(18) 0.51958(12) 0.0203 1.0000 Uani . . . . . .
C61 C 0.8164(2) 0.82730(19) 0.55575(12) 0.0227 1.0000 Uani . . . . . .
C62 C 0.6989(2) 0.89090(19) 0.54597(12) 0.0245 1.0000 Uani . . . . . .
C63 C 0.6201(2) 0.87619(18) 0.49999(12) 0.0192 1.0000 Uani . . . . . .
C64 C 0.4721(2) 0.48618(17) 0.40288(11) 0.0172 1.0000 Uani . . . . . .
C65 C 0.4279(2) 0.39859(17) 0.39756(11) 0.0190 1.0000 Uani . . . . . .
C66 C 0.3428(2) 0.40122(17) 0.35000(12) 0.0191 1.0000 Uani . . . . . .
C67 C 0.3040(2) 0.49223(17) 0.30976(11) 0.0166 1.0000 Uani . . . . . .
P68 P 0.69639(6) 0.70018(5) 0.00867(3) 0.0225 1.0000 Uani . . . . . .
F69 F 0.77667(18) 0.58634(13) 0.01902(9) 0.0436 1.0000 Uani . . . . . .
F70 F 0.82438(15) 0.74407(12) -0.00333(8) 0.0330 1.0000 Uani . . . . . .
F71 F 0.69106(18) 0.69574(14) -0.06731(8) 0.0401 1.0000 Uani . . . . . .
F72 F 0.56872(17) 0.65628(14) 0.02092(9) 0.0439 1.0000 Uani . . . . . .
F73 F 0.61723(17) 0.81386(13) -0.00234(10) 0.0442 1.0000 Uani . . . . . .
F74 F 0.70182(19) 0.70365(16) 0.08437(8) 0.0467 1.0000 Uani . . . . . .
C75 C 0.8873(3) 0.27650(19) 0.22904(14) 0.0277 1.0000 Uani . . . . . .
C76 C 0.8692(3) 0.26974(19) 0.29561(14) 0.0282 1.0000 Uani . . . . . .
C77 C 0.9398(2) 0.3161(2) 0.33103(13) 0.0260 1.0000 Uani . . . . . .
C78 C 1.0280(2) 0.36918(19) 0.29919(13) 0.0257 1.0000 Uani . . . . . .
C79 C 1.0462(2) 0.37691(18) 0.23190(13) 0.0238 1.0000 Uani . . . . . .
C80 C 0.9759(3) 0.33044(19) 0.19620(13) 0.0261 1.0000 Uani . . . . . .
C81 C 0.9940(3) 0.3378(3) 0.12388(15) 0.0411 1.0000 Uani . . . . . .
C82 C -0.1346(3) 0.9211(2) 0.10416(14) 0.0346 1.0000 Uani . . . . . .
C83 C -0.1809(3) 1.0327(2) 0.08121(12) 0.0281 1.0000 Uani . . . . . .
C84 C -0.1029(3) 1.0916(2) 0.04328(13) 0.0300 1.0000 Uani . . . . . .
C85 C -0.1477(3) 1.1927(2) 0.01950(14) 0.0340 1.0000 Uani . . . . . .
C86 C -0.2686(3) 1.2381(2) 0.03195(14) 0.0341 1.0000 Uani . . . . . .
C87 C -0.3473(3) 1.1815(2) 0.07113(14) 0.0345 1.0000 Uani . . . . . .
C88 C -0.3020(3) 1.0800(2) 0.09498(13) 0.0321 1.0000 Uani . . . . . .
H41 H 0.0930 1.0412 0.1369 0.0205 1.0000 Uiso R . . . . .
H51 H 0.2288 1.0558 0.0459 0.0233 1.0000 Uiso R . . . . .
H61 H 0.4049 0.9250 0.0363 0.0221 1.0000 Uiso R . . . . .
H71 H 0.4394 0.7845 0.1180 0.0191 1.0000 Uiso R . . . . .
H111 H -0.0353 0.8586 0.4048 0.0183 1.0000 Uiso R . . . . .
H131 H -0.0260 1.0119 0.2231 0.0176 1.0000 Uiso R . . . . .
H151 H -0.2451 1.0386 0.2404 0.0250 1.0000 Uiso R . . . . .
H161 H -0.4334 1.1454 0.2637 0.0313 1.0000 Uiso R . . . . .
H171 H -0.4794 1.1837 0.3690 0.0336 1.0000 Uiso R . . . . .
H181 H -0.3331 1.1178 0.4498 0.0332 1.0000 Uiso R . . . . .
H191 H -0.1433 1.0122 0.4268 0.0273 1.0000 Uiso R . . . . .
H211 H 0.0742 0.6000 0.3763 0.0221 1.0000 Uiso R . . . . .
H221 H 0.1228 0.4804 0.4692 0.0284 1.0000 Uiso R . . . . .
H231 H 0.2282 0.5209 0.5536 0.0298 1.0000 Uiso R . . . . .
H241 H 0.2850 0.6813 0.5442 0.0285 1.0000 Uiso R . . . . .
H251 H 0.2369 0.7998 0.4515 0.0228 1.0000 Uiso R . . . . .
H281 H 0.7329 0.4700 0.1731 0.0306 1.0000 Uiso R . . . . .
H291 H 0.6275 0.3881 0.1101 0.0393 1.0000 Uiso R . . . . .
H301 H 0.4114 0.4468 0.0942 0.0324 1.0000 Uiso R . . . . .
H341 H 0.0294 0.7201 0.2187 0.0238 1.0000 Uiso R . . . . .
H351 H -0.0918 0.6732 0.1443 0.0279 1.0000 Uiso R . . . . .
H361 H 0.0109 0.5788 0.0648 0.0287 1.0000 Uiso R . . . . .
H371 H 0.2298 0.5258 0.0660 0.0281 1.0000 Uiso R . . . . .
H391 H 0.7439 0.4871 0.2859 0.0242 1.0000 Uiso R . . . . .
H401 H 0.8767 0.5578 0.3421 0.0281 1.0000 Uiso R . . . . .
H411 H 0.8680 0.7343 0.3256 0.0263 1.0000 Uiso R . . . . .
H421 H 0.7266 0.8398 0.2527 0.0255 1.0000 Uiso R . . . . .
H431 H 0.5928 0.7699 0.1962 0.0214 1.0000 Uiso R . . . . .
H501 H 0.2362 0.9924 0.3421 0.0199 1.0000 Uiso R . . . . .
H511 H 0.1605 1.1547 0.2860 0.0248 1.0000 Uiso R . . . . .
H521 H 0.2582 1.2117 0.1882 0.0270 1.0000 Uiso R . . . . .
H531 H 0.4324 1.1067 0.1469 0.0250 1.0000 Uiso R . . . . .
H541 H 0.5110 0.9455 0.2037 0.0207 1.0000 Uiso R . . . . .
H551 H 0.5213 0.9318 0.3747 0.0168 1.0000 Uiso R . . . . .
H571 H 0.5814 0.6298 0.4396 0.0161 1.0000 Uiso R . . . . .
H591 H 0.7977 0.6784 0.4495 0.0200 1.0000 Uiso R . . . . .
H601 H 0.9323 0.7045 0.5260 0.0243 1.0000 Uiso R . . . . .
H611 H 0.8710 0.8380 0.5869 0.0273 1.0000 Uiso R . . . . .
H621 H 0.6729 0.9446 0.5710 0.0294 1.0000 Uiso R . . . . .
H631 H 0.5408 0.9207 0.4934 0.0231 1.0000 Uiso R . . . . .
H641 H 0.5307 0.4853 0.4352 0.0207 1.0000 Uiso R . . . . .
H651 H 0.4556 0.3372 0.4262 0.0229 1.0000 Uiso R . . . . .
H661 H 0.3117 0.3417 0.3452 0.0229 1.0000 Uiso R . . . . .
H671 H 0.2457 0.4942 0.2771 0.0199 1.0000 Uiso R . . . . .
H751 H 0.8387 0.2440 0.2053 0.0333 1.0000 Uiso R . . . . .
H761 H 0.8082 0.2332 0.3171 0.0339 1.0000 Uiso R . . . . .
H771 H 0.9277 0.3114 0.3768 0.0312 1.0000 Uiso R . . . . .
H781 H 1.0768 0.4009 0.3233 0.0309 1.0000 Uiso R . . . . .
H791 H 1.1069 0.4140 0.2105 0.0285 1.0000 Uiso R . . . . .
H811 H 1.0574 0.3769 0.1096 0.0493 1.0000 Uiso R . . . . .
H812 H 1.0193 0.2712 0.1125 0.0493 1.0000 Uiso R . . . . .
H813 H 0.9170 0.3699 0.1037 0.0493 1.0000 Uiso R . . . . .
H821 H -0.1996 0.8934 0.1291 0.0415 1.0000 Uiso R . . . . .
H822 H -0.0630 0.9130 0.1301 0.0415 1.0000 Uiso R . . . . .
H823 H -0.1120 0.8864 0.0677 0.0415 1.0000 Uiso R . . . . .
H841 H -0.0181 1.0617 0.0338 0.0360 1.0000 Uiso R . . . . .
H851 H -0.0930 1.2314 -0.0061 0.0409 1.0000 Uiso R . . . . .
H861 H -0.2991 1.3073 0.0143 0.0410 1.0000 Uiso R . . . . .
H871 H -0.4313 1.2124 0.0814 0.0414 1.0000 Uiso R . . . . .
H881 H -0.3562 1.0420 0.1216 0.0386 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.086506(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 . N2 . 2.0479(18) yes
Ir1 . C9 . 2.031(2) yes
Ir1 . N26 . 2.2610(18) yes
Ir1 . N33 . 2.1454(19) yes
Ir1 . N44 . 2.0549(18) yes
Ir1 . C47 . 2.047(2) yes
N2 . C3 . 1.356(3) yes
N2 . C7 . 1.343(3) yes
C3 . C4 . 1.399(3) yes
C3 . C8 . 1.460(3) yes
C4 . C5 . 1.381(3) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.388(3) yes
C5 . H51 . 0.950 no
C6 . C7 . 1.386(3) yes
C6 . H61 . 0.950 no
C7 . H71 . 0.950 no
C8 . C9 . 1.423(3) yes
C8 . C13 . 1.404(3) yes
C9 . C10 . 1.401(3) yes
C10 . C11 . 1.404(3) yes
C10 . C20 . 1.497(3) yes
C11 . C12 . 1.393(3) yes
C11 . H111 . 0.950 no
C12 . C13 . 1.392(3) yes
C12 . C14 . 1.487(3) yes
C13 . H131 . 0.950 no
C14 . C15 . 1.401(3) yes
C14 . C19 . 1.395(3) yes
C15 . C16 . 1.388(3) yes
C15 . H151 . 0.950 no
C16 . C17 . 1.387(4) yes
C16 . H161 . 0.950 no
C17 . C18 . 1.381(4) yes
C17 . H171 . 0.950 no
C18 . C19 . 1.392(3) yes
C18 . H181 . 0.950 no
C19 . H191 . 0.950 no
C20 . C21 . 1.391(3) yes
C20 . C25 . 1.395(3) yes
C21 . C22 . 1.391(3) yes
C21 . H211 . 0.950 no
C22 . C23 . 1.390(4) yes
C22 . H221 . 0.950 no
C23 . C24 . 1.389(4) yes
C23 . H231 . 0.950 no
C24 . C25 . 1.383(3) yes
C24 . H241 . 0.950 no
C25 . H251 . 0.950 no
N26 . C27 . 1.348(3) yes
N26 . C31 . 1.368(3) yes
C27 . C28 . 1.407(3) yes
C27 . C38 . 1.480(3) yes
C28 . C29 . 1.364(4) yes
C28 . H281 . 0.950 no
C29 . C30 . 1.378(4) yes
C29 . H291 . 0.950 no
C30 . C31 . 1.391(3) yes
C30 . H301 . 0.950 no
C31 . C32 . 1.478(3) yes
C32 . N33 . 1.341(3) yes
C32 . C37 . 1.406(3) yes
N33 . C34 . 1.347(3) yes
C34 . C35 . 1.382(3) yes
C34 . H341 . 0.950 no
C35 . C36 . 1.382(4) yes
C35 . H351 . 0.950 no
C36 . C37 . 1.378(4) yes
C36 . H361 . 0.950 no
C37 . H371 . 0.950 no
C38 . C39 . 1.399(3) yes
C38 . C43 . 1.393(3) yes
C39 . C40 . 1.385(4) yes
C39 . H391 . 0.950 no
C40 . C41 . 1.389(4) yes
C40 . H401 . 0.950 no
C41 . C42 . 1.382(4) yes
C41 . H411 . 0.950 no
C42 . C43 . 1.389(3) yes
C42 . H421 . 0.950 no
C43 . H431 . 0.950 no
N44 . C45 . 1.352(3) yes
N44 . C67 . 1.348(3) yes
C45 . C46 . 1.462(3) yes
C45 . C64 . 1.401(3) yes
C46 . C47 . 1.422(3) yes
C46 . C57 . 1.395(3) yes
C47 . C48 . 1.416(3) yes
C48 . C49 . 1.503(3) yes
C48 . C55 . 1.403(3) yes
C49 . C50 . 1.394(3) yes
C49 . C54 . 1.396(3) yes
C50 . C51 . 1.393(3) yes
C50 . H501 . 0.950 no
C51 . C52 . 1.380(4) yes
C51 . H511 . 0.950 no
C52 . C53 . 1.386(4) yes
C52 . H521 . 0.950 no
C53 . C54 . 1.392(3) yes
C53 . H531 . 0.950 no
C54 . H541 . 0.950 no
C55 . C56 . 1.396(3) yes
C55 . H551 . 0.950 no
C56 . C57 . 1.383(3) yes
C56 . C58 . 1.485(3) yes
C57 . H571 . 0.950 no
C58 . C59 . 1.398(3) yes
C58 . C63 . 1.390(3) yes
C59 . C60 . 1.391(3) yes
C59 . H591 . 0.950 no
C60 . C61 . 1.384(4) yes
C60 . H601 . 0.950 no
C61 . C62 . 1.394(4) yes
C61 . H611 . 0.950 no
C62 . C63 . 1.382(3) yes
C62 . H621 . 0.950 no
C63 . H631 . 0.950 no
C64 . C65 . 1.381(3) yes
C64 . H641 . 0.950 no
C65 . C66 . 1.385(3) yes
C65 . H651 . 0.950 no
C66 . C67 . 1.382(3) yes
C66 . H661 . 0.950 no
C67 . H671 . 0.950 no
P68 . F69 . 1.6011(18) yes
P68 . F70 . 1.5994(16) yes
P68 . F71 . 1.6017(16) yes
P68 . F72 . 1.5966(17) yes
P68 . F73 . 1.5950(18) yes
P68 . F74 . 1.5933(17) yes
C75 . C76 . 1.383(4) yes
C75 . C80 . 1.398(4) yes
C75 . H751 . 0.950 no
C76 . C77 . 1.386(4) yes
C76 . H761 . 0.950 no
C77 . C78 . 1.380(4) yes
C77 . H771 . 0.950 no
C78 . C79 . 1.397(4) yes
C78 . H781 . 0.950 no
C79 . C80 . 1.389(4) yes
C79 . H791 . 0.950 no
C80 . C81 . 1.501(4) yes
C81 . H811 . 0.950 no
C81 . H812 . 0.950 no
C81 . H813 . 0.950 no
C82 . C83 . 1.503(4) yes
C82 . H821 . 0.950 no
C82 . H822 . 0.950 no
C82 . H823 . 0.950 no
C83 . C84 . 1.398(4) yes
C83 . C88 . 1.376(4) yes
C84 . C85 . 1.380(4) yes
C84 . H841 . 0.950 no
C85 . C86 . 1.360(4) yes
C85 . H851 . 0.950 no
C86 . C87 . 1.396(4) yes
C86 . H861 . 0.950 no
C87 . C88 . 1.386(4) yes
C87 . H871 . 0.950 no
C88 . H881 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 . Ir1 . C9 . 80.64(8) yes
N2 . Ir1 . N26 . 94.32(7) yes
C9 . Ir1 . N26 . 169.36(7) yes
N2 . Ir1 . N33 . 83.03(7) yes
C9 . Ir1 . N33 . 93.87(8) yes
N26 . Ir1 . N33 . 76.14(7) yes
N2 . Ir1 . N44 . 174.85(7) yes
C9 . Ir1 . N44 . 104.46(8) yes
N26 . Ir1 . N44 . 80.53(7) yes
N33 . Ir1 . N44 . 95.77(7) yes
N2 . Ir1 . C47 . 101.37(8) yes
C9 . Ir1 . C47 . 83.91(8) yes
N26 . Ir1 . C47 . 106.35(7) yes
N33 . Ir1 . C47 . 174.64(8) yes
N44 . Ir1 . C47 . 80.11(8) yes
Ir1 . N2 . C3 . 115.66(14) yes
Ir1 . N2 . C7 . 124.19(15) yes
C3 . N2 . C7 . 119.95(19) yes
N2 . C3 . C4 . 120.0(2) yes
N2 . C3 . C8 . 114.22(19) yes
C4 . C3 . C8 . 125.7(2) yes
C3 . C4 . C5 . 120.0(2) yes
C3 . C4 . H41 . 120.0 no
C5 . C4 . H41 . 120.0 no
C4 . C5 . C6 . 119.2(2) yes
C4 . C5 . H51 . 120.4 no
C6 . C5 . H51 . 120.4 no
C5 . C6 . C7 . 118.6(2) yes
C5 . C6 . H61 . 120.7 no
C7 . C6 . H61 . 120.7 no
C6 . C7 . N2 . 122.1(2) yes
C6 . C7 . H71 . 118.9 no
N2 . C7 . H71 . 118.9 no
C3 . C8 . C9 . 115.94(19) yes
C3 . C8 . C13 . 121.6(2) yes
C9 . C8 . C13 . 122.4(2) yes
C8 . C9 . Ir1 . 112.49(15) yes
C8 . C9 . C10 . 115.86(19) yes
Ir1 . C9 . C10 . 131.65(16) yes
C9 . C10 . C11 . 120.9(2) yes
C9 . C10 . C20 . 125.04(19) yes
C11 . C10 . C20 . 114.08(19) yes
C10 . C11 . C12 . 122.6(2) yes
C10 . C11 . H111 . 118.7 no
C12 . C11 . H111 . 118.7 no
C11 . C12 . C13 . 117.4(2) yes
C11 . C12 . C14 . 121.0(2) yes
C13 . C12 . C14 . 121.6(2) yes
C8 . C13 . C12 . 120.5(2) yes
C8 . C13 . H131 . 119.8 no
C12 . C13 . H131 . 119.8 no
C12 . C14 . C15 . 120.8(2) yes
C12 . C14 . C19 . 121.4(2) yes
C15 . C14 . C19 . 117.8(2) yes
C14 . C15 . C16 . 121.2(2) yes
C14 . C15 . H151 . 119.4 no
C16 . C15 . H151 . 119.4 no
C15 . C16 . C17 . 120.2(2) yes
C15 . C16 . H161 . 119.9 no
C17 . C16 . H161 . 119.9 no
C16 . C17 . C18 . 119.4(2) yes
C16 . C17 . H171 . 120.3 no
C18 . C17 . H171 . 120.3 no
C17 . C18 . C19 . 120.7(2) yes
C17 . C18 . H181 . 119.7 no
C19 . C18 . H181 . 119.7 no
C14 . C19 . C18 . 120.8(2) yes
C14 . C19 . H191 . 119.6 no
C18 . C19 . H191 . 119.6 no
C10 . C20 . C21 . 121.3(2) yes
C10 . C20 . C25 . 120.1(2) yes
C21 . C20 . C25 . 118.3(2) yes
C20 . C21 . C22 . 120.9(2) yes
C20 . C21 . H211 . 119.5 no
C22 . C21 . H211 . 119.5 no
C21 . C22 . C23 . 119.9(2) yes
C21 . C22 . H221 . 120.0 no
C23 . C22 . H221 . 120.0 no
C22 . C23 . C24 . 119.6(2) yes
C22 . C23 . H231 . 120.2 no
C24 . C23 . H231 . 120.2 no
C23 . C24 . C25 . 120.0(2) yes
C23 . C24 . H241 . 120.0 no
C25 . C24 . H241 . 120.0 no
C20 . C25 . C24 . 121.2(2) yes
C20 . C25 . H251 . 119.4 no
C24 . C25 . H251 . 119.4 no
Ir1 . N26 . C27 . 129.54(15) yes
Ir1 . N26 . C31 . 111.66(15) yes
C27 . N26 . C31 . 117.57(19) yes
N26 . C27 . C28 . 121.5(2) yes
N26 . C27 . C38 . 122.1(2) yes
C28 . C27 . C38 . 116.3(2) yes
C27 . C28 . C29 . 120.2(2) yes
C27 . C28 . H281 . 119.9 no
C29 . C28 . H281 . 119.9 no
C28 . C29 . C30 . 119.1(2) yes
C28 . C29 . H291 . 120.5 no
C30 . C29 . H291 . 120.5 no
C29 . C30 . C31 . 119.1(2) yes
C29 . C30 . H301 . 120.4 no
C31 . C30 . H301 . 120.4 no
C30 . C31 . N26 . 122.5(2) yes
C30 . C31 . C32 . 119.9(2) yes
N26 . C31 . C32 . 117.5(2) yes
C31 . C32 . N33 . 116.3(2) yes
C31 . C32 . C37 . 122.8(2) yes
N33 . C32 . C37 . 120.8(2) yes
Ir1 . N33 . C32 . 117.08(15) yes
Ir1 . N33 . C34 . 123.38(16) yes
C32 . N33 . C34 . 119.2(2) yes
N33 . C34 . C35 . 122.8(2) yes
N33 . C34 . H341 . 118.6 no
C35 . C34 . H341 . 118.6 no
C34 . C35 . C36 . 118.1(2) yes
C34 . C35 . H351 . 120.9 no
C36 . C35 . H351 . 120.9 no
C35 . C36 . C37 . 119.8(2) yes
C35 . C36 . H361 . 120.1 no
C37 . C36 . H361 . 120.1 no
C32 . C37 . C36 . 119.2(2) yes
C32 . C37 . H371 . 120.4 no
C36 . C37 . H371 . 120.4 no
C27 . C38 . C39 . 118.5(2) yes
C27 . C38 . C43 . 122.1(2) yes
C39 . C38 . C43 . 119.1(2) yes
C38 . C39 . C40 . 120.3(2) yes
C38 . C39 . H391 . 119.8 no
C40 . C39 . H391 . 119.8 no
C39 . C40 . C41 . 120.1(2) yes
C39 . C40 . H401 . 120.0 no
C41 . C40 . H401 . 120.0 no
C40 . C41 . C42 . 120.0(2) yes
C40 . C41 . H411 . 120.0 no
C42 . C41 . H411 . 120.0 no
C41 . C42 . C43 . 120.3(2) yes
C41 . C42 . H421 . 119.9 no
C43 . C42 . H421 . 119.9 no
C38 . C43 . C42 . 120.3(2) yes
C38 . C43 . H431 . 119.9 no
C42 . C43 . H431 . 119.9 no
Ir1 . N44 . C45 . 115.83(14) yes
Ir1 . N44 . C67 . 123.72(15) yes
C45 . N44 . C67 . 119.54(19) yes
N44 . C45 . C46 . 114.23(19) yes
N44 . C45 . C64 . 120.1(2) yes
C46 . C45 . C64 . 125.7(2) yes
C45 . C46 . C47 . 115.91(19) yes
C45 . C46 . C57 . 120.88(19) yes
C47 . C46 . C57 . 123.2(2) yes
C46 . C47 . Ir1 . 112.69(15) yes
C46 . C47 . C48 . 115.32(19) yes
Ir1 . C47 . C48 . 131.70(16) yes
C47 . C48 . C49 . 125.75(19) yes
C47 . C48 . C55 . 120.35(19) yes
C49 . C48 . C55 . 113.90(19) yes
C48 . C49 . C50 . 119.1(2) yes
C48 . C49 . C54 . 122.2(2) yes
C50 . C49 . C54 . 118.3(2) yes
C49 . C50 . C51 . 121.1(2) yes
C49 . C50 . H501 . 119.4 no
C51 . C50 . H501 . 119.4 no
C50 . C51 . C52 . 119.9(2) yes
C50 . C51 . H511 . 120.1 no
C52 . C51 . H511 . 120.1 no
C51 . C52 . C53 . 119.8(2) yes
C51 . C52 . H521 . 120.1 no
C53 . C52 . H521 . 120.1 no
C52 . C53 . C54 . 120.3(2) yes
C52 . C53 . H531 . 119.8 no
C54 . C53 . H531 . 119.8 no
C49 . C54 . C53 . 120.5(2) yes
C49 . C54 . H541 . 119.7 no
C53 . C54 . H541 . 119.7 no
C48 . C55 . C56 . 122.7(2) yes
C48 . C55 . H551 . 118.7 no
C56 . C55 . H551 . 118.7 no
C55 . C56 . C57 . 117.7(2) yes
C55 . C56 . C58 . 121.07(19) yes
C57 . C56 . C58 . 121.2(2) yes
C46 . C57 . C56 . 120.3(2) yes
C46 . C57 . H571 . 119.8 no
C56 . C57 . H571 . 119.8 no
C56 . C58 . C59 . 121.2(2) yes
C56 . C58 . C63 . 120.5(2) yes
C59 . C58 . C63 . 118.3(2) yes
C58 . C59 . C60 . 120.8(2) yes
C58 . C59 . H591 . 119.6 no
C60 . C59 . H591 . 119.6 no
C59 . C60 . C61 . 120.2(2) yes
C59 . C60 . H601 . 119.9 no
C61 . C60 . H601 . 119.9 no
C60 . C61 . C62 . 119.3(2) yes
C60 . C61 . H611 . 120.3 no
C62 . C61 . H611 . 120.3 no
C61 . C62 . C63 . 120.3(2) yes
C61 . C62 . H621 . 119.8 no
C63 . C62 . H621 . 119.8 no
C58 . C63 . C62 . 121.0(2) yes
C58 . C63 . H631 . 119.5 no
C62 . C63 . H631 . 119.5 no
C45 . C64 . C65 . 120.0(2) yes
C45 . C64 . H641 . 120.0 no
C65 . C64 . H641 . 120.0 no
C64 . C65 . C66 . 119.2(2) yes
C64 . C65 . H651 . 120.4 no
C66 . C65 . H651 . 120.4 no
C65 . C66 . C67 . 118.6(2) yes
C65 . C66 . H661 . 120.7 no
C67 . C66 . H661 . 120.7 no
C66 . C67 . N44 . 122.5(2) yes
C66 . C67 . H671 . 118.7 no
N44 . C67 . H671 . 118.7 no
F69 . P68 . F70 . 89.85(10) yes
F69 . P68 . F71 . 89.88(10) yes
F70 . P68 . F71 . 90.36(9) yes
F69 . P68 . F72 . 90.10(10) yes
F70 . P68 . F72 . 179.80(10) yes
F71 . P68 . F72 . 89.83(10) yes
F69 . P68 . F73 . 179.39(11) yes
F70 . P68 . F73 . 89.77(9) yes
F71 . P68 . F73 . 89.64(11) yes
F72 . P68 . F73 . 90.29(10) yes
F69 . P68 . F74 . 89.71(11) yes
F70 . P68 . F74 . 89.84(10) yes
F71 . P68 . F74 . 179.55(11) yes
F72 . P68 . F74 . 89.97(10) yes
F73 . P68 . F74 . 90.76(11) yes
C76 . C75 . C80 . 121.0(2) yes
C76 . C75 . H751 . 119.5 no
C80 . C75 . H751 . 119.5 no
C75 . C76 . C77 . 120.2(2) yes
C75 . C76 . H761 . 119.9 no
C77 . C76 . H761 . 119.9 no
C76 . C77 . C78 . 119.3(2) yes
C76 . C77 . H771 . 120.3 no
C78 . C77 . H771 . 120.3 no
C77 . C78 . C79 . 120.8(2) yes
C77 . C78 . H781 . 119.6 no
C79 . C78 . H781 . 119.6 no
C78 . C79 . C80 . 120.1(2) yes
C78 . C79 . H791 . 119.9 no
C80 . C79 . H791 . 119.9 no
C75 . C80 . C79 . 118.6(2) yes
C75 . C80 . C81 . 120.5(3) yes
C79 . C80 . C81 . 121.0(3) yes
C80 . C81 . H811 . 109.5 no
C80 . C81 . H812 . 109.5 no
H811 . C81 . H812 . 109.5 no
C80 . C81 . H813 . 109.5 no
H811 . C81 . H813 . 109.5 no
H812 . C81 . H813 . 109.5 no
C83 . C82 . H821 . 109.5 no
C83 . C82 . H822 . 109.5 no
H821 . C82 . H822 . 109.5 no
C83 . C82 . H823 . 109.5 no
H821 . C82 . H823 . 109.5 no
H822 . C82 . H823 . 109.5 no
C82 . C83 . C84 . 120.9(3) yes
C82 . C83 . C88 . 121.6(3) yes
C84 . C83 . C88 . 117.5(3) yes
C83 . C84 . C85 . 120.8(3) yes
C83 . C84 . H841 . 119.6 no
C85 . C84 . H841 . 119.6 no
C84 . C85 . C86 . 121.3(3) yes
C84 . C85 . H851 . 119.3 no
C86 . C85 . H851 . 119.3 no
C85 . C86 . C87 . 118.9(3) yes
C85 . C86 . H861 . 120.5 no
C87 . C86 . H861 . 120.5 no
C86 . C87 . C88 . 119.6(3) yes
C86 . C87 . H871 . 120.2 no
C88 . C87 . H871 . 120.2 no
C87 . C88 . C83 . 121.8(3) yes
C87 . C88 . H881 . 119.1 no
C83 . C88 . H881 . 119.1 no


