# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_hhb
_database_code_depnum_ccdc_archive 'CCDC 1584485'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;
_audit_creation_date             2017-08-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C42 H28 F5.98 Ir N9 O2 P2'
_chemical_formula_sum            'C42 H28 F5.98 Ir N9 O2 P2'
_chemical_formula_weight         1058.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5095(6)
_cell_length_b                   16.3355(9)
_cell_length_c                   22.6258(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.9900(10)
_cell_angle_gamma                90
_cell_volume                     4189.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8706
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.882
_cell_measurement_theta_min      2.187
_shelx_estimated_absorpt_T_max   0.690
_shelx_estimated_absorpt_T_min   0.415
_exptl_absorpt_coefficient_mu    3.339
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0752 before and 0.0421 after correction. The Ratio of minimum to maximum transmission is 0.7889. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2079
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29798
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.259
_diffrn_reflns_theta_min         1.546
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8069
_reflns_number_total             10356
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     692
_refine_ls_number_reflns         10356
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²+1.1863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0645
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F6) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Sof(F2A)=1-FVAR(1)
 Sof(F2)=FVAR(1)
 Sof(F3A)=1-FVAR(2)
 Sof(F3)=FVAR(2)
 Sof(F4A)=1-FVAR(3)
 Sof(F4)=FVAR(3)
 Sof(F1A)=1-FVAR(4)
 Sof(F1)=FVAR(4)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C15(H15), C16(H16), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.28395(2) 0.36206(2) 0.19569(2) 0.02981(4) Uani 1 1 d . . . . .
P1 P 0.32757(7) 0.42609(5) 0.33649(4) 0.03690(19) Uani 1 1 d . . . . .
P2 P 0.09509(7) 0.44336(5) 0.27278(4) 0.03363(18) Uani 1 1 d . . . . .
F5 F -0.0976(4) 0.1600(3) 0.0221(3) 0.208(3) Uani 1 1 d . . . . .
O1 O 0.37978(18) 0.41364(13) 0.27979(9) 0.0398(5) Uani 1 1 d . . . . .
O2 O 0.11443(18) 0.37933(12) 0.22706(10) 0.0361(5) Uani 1 1 d . . . . .
N1 N 0.1939(2) 0.4532(2) 0.33019(13) 0.0529(8) Uani 1 1 d . . . . .
N2 N 0.6460(3) 0.2823(2) 0.14120(16) 0.0605(9) Uani 1 1 d . . . . .
N3 N 0.4915(3) 0.38209(17) 0.13482(13) 0.0453(7) Uani 1 1 d . . . . .
N4 N 0.4496(3) 0.13995(17) 0.24979(16) 0.0529(8) Uani 1 1 d . . . . .
N5 N 0.3088(2) 0.24682(15) 0.23079(11) 0.0328(6) Uani 1 1 d . . . . .
N6 N 0.1423(3) 0.25205(18) 0.10774(13) 0.0490(7) Uani 1 1 d . . . . .
N7 N 0.0174(3) 0.3017(2) 0.01894(15) 0.0671(10) Uani 1 1 d . . . . .
N8 N 0.2666(2) 0.47267(15) 0.15291(11) 0.0340(6) Uani 1 1 d . . . . .
N9 N 0.1784(3) 0.53746(19) 0.06200(13) 0.0520(8) Uani 1 1 d . . . . .
C1 C 0.4140(3) 0.5019(2) 0.38174(16) 0.0470(9) Uani 1 1 d . . . . .
C2 C 0.5237(4) 0.5235(3) 0.3709(2) 0.0642(12) Uani 1 1 d . . . . .
H2 H 0.556(3) 0.499(2) 0.3425(15) 0.041(11) Uiso 1 1 d . . . . .
C3 C 0.5893(6) 0.5838(4) 0.4067(3) 0.098(2) Uani 1 1 d . . . . .
H3 H 0.670(4) 0.588(3) 0.399(2) 0.083(16) Uiso 1 1 d . . . . .
C4 C 0.5449(7) 0.6187(4) 0.4521(3) 0.109(3) Uani 1 1 d . . . . .
H4 H 0.594(4) 0.660(3) 0.471(2) 0.102(17) Uiso 1 1 d . . . . .
C5 C 0.4358(7) 0.5993(4) 0.4617(3) 0.113(2) Uani 1 1 d . . . . .
H5 H 0.405205 0.625830 0.491973 0.136 Uiso 1 1 calc R . . . .
C6 C 0.3691(5) 0.5410(3) 0.4275(2) 0.0774(14) Uani 1 1 d . . . . .
H6 H 0.294382 0.527687 0.435019 0.093 Uiso 1 1 calc R . . . .
C7 C 0.3444(3) 0.3318(2) 0.37980(15) 0.0383(7) Uani 1 1 d . . . . .
C8 C 0.4469(4) 0.2866(3) 0.3857(2) 0.0670(13) Uani 1 1 d . . . . .
H8 H 0.503(4) 0.303(3) 0.370(2) 0.086(17) Uiso 1 1 d . . . . .
C9 C 0.4592(5) 0.2156(3) 0.4197(2) 0.0828(16) Uani 1 1 d . . . . .
H9 H 0.538(5) 0.196(3) 0.427(2) 0.12(2) Uiso 1 1 d . . . . .
C10 C 0.3709(5) 0.1892(3) 0.4471(2) 0.0725(13) Uani 1 1 d . . . . .
H10 H 0.376(4) 0.138(2) 0.4704(19) 0.067(13) Uiso 1 1 d . . . . .
C11 C 0.2695(5) 0.2333(3) 0.4414(2) 0.0714(13) Uani 1 1 d . . . . .
H11 H 0.208(4) 0.217(3) 0.4603(19) 0.075(13) Uiso 1 1 d . . . . .
C12 C 0.2555(3) 0.3040(3) 0.40813(19) 0.0573(10) Uani 1 1 d . . . . .
H12 H 0.178(4) 0.344(3) 0.405(2) 0.093(16) Uiso 1 1 d . . . . .
C13 C -0.0416(3) 0.4225(2) 0.29790(16) 0.0399(8) Uani 1 1 d . . . . .
C14 C -0.0497(4) 0.4309(3) 0.3579(2) 0.0702(13) Uani 1 1 d . . . . .
H14 H 0.022(4) 0.448(3) 0.385(2) 0.097(17) Uiso 1 1 d . . . . .
C15 C -0.1546(5) 0.4155(4) 0.3773(3) 0.1007(19) Uani 1 1 d . . . . .
H15 H -0.159614 0.421114 0.417668 0.121 Uiso 1 1 calc R . . . .
C16 C -0.2510(5) 0.3921(3) 0.3371(3) 0.0946(19) Uani 1 1 d . . . . .
H16 H -0.320882 0.379922 0.350628 0.113 Uiso 1 1 calc R . . . .
C17 C -0.2470(4) 0.3860(3) 0.2769(3) 0.0751(14) Uani 1 1 d . . . . .
H17 H -0.320(4) 0.373(3) 0.246(2) 0.091(16) Uiso 1 1 d . . . . .
C18 C -0.1410(3) 0.4013(2) 0.2577(2) 0.0540(10) Uani 1 1 d . . . . .
H18 H -0.137(3) 0.393(2) 0.2170(18) 0.056(12) Uiso 1 1 d . . . . .
C19 C 0.0710(3) 0.54131(19) 0.23594(17) 0.0414(8) Uani 1 1 d . . . . .
C20 C 0.0136(3) 0.5472(2) 0.17711(19) 0.0499(9) Uani 1 1 d . . . . .
H20 H -0.013(3) 0.4979(18) 0.1568(13) 0.029(8) Uiso 1 1 d . . . . .
C21 C -0.0043(5) 0.6253(4) 0.1507(3) 0.0758(15) Uani 1 1 d . . . . .
H21 H -0.048(4) 0.619(3) 0.112(2) 0.088(17) Uiso 1 1 d . . . . .
C22 C 0.0349(5) 0.6932(3) 0.1843(3) 0.0905(18) Uani 1 1 d . . . . .
H22 H 0.023657 0.744568 0.166504 0.109 Uiso 1 1 calc R . . . .
C23 C 0.0893(5) 0.6880(3) 0.2421(3) 0.0873(17) Uani 1 1 d . . . . .
H23 H 0.121(4) 0.740(3) 0.265(2) 0.099(17) Uiso 1 1 d . . . . .
C24 C 0.1080(4) 0.6125(2) 0.2674(3) 0.0633(12) Uani 1 1 d . . . . .
H24 H 0.146(4) 0.608(2) 0.3090(19) 0.064(13) Uiso 1 1 d . . . . .
C25 C 0.0106(7) 0.1591(4) 0.0471(3) 0.0973(19) Uani 1 1 d . . . . .
C26 C 0.0613(4) 0.2454(3) 0.05815(18) 0.0596(11) Uani 1 1 d . . . . .
C27 C 0.1853(3) 0.3277(2) 0.12034(14) 0.0357(7) Uani 1 1 d . . . . .
C28 C 0.0639(4) 0.3765(3) 0.03040(18) 0.0573(11) Uani 1 1 d . . . . .
H28 H 0.034(4) 0.418(2) 0.0036(19) 0.073(13) Uiso 1 1 d . . . . .
C29 C 0.1476(3) 0.3923(2) 0.07985(15) 0.0409(8) Uani 1 1 d . . . . .
C30 C 0.1993(3) 0.4724(2) 0.09712(15) 0.0410(8) Uani 1 1 d . . . . .
C31 C 0.3161(3) 0.5434(2) 0.17333(18) 0.0440(8) Uani 1 1 d . . . . .
H31 H 0.356(3) 0.5415(18) 0.2092(14) 0.031(9) Uiso 1 1 d . . . . .
C32 C 0.2271(4) 0.6074(3) 0.0835(2) 0.0567(10) Uani 1 1 d . . . . .
H32 H 0.212(3) 0.660(2) 0.0572(17) 0.063(11) Uiso 1 1 d . . . . .
C33 C 0.2967(3) 0.6133(2) 0.1393(2) 0.0530(10) Uani 1 1 d . . . . .
H33 H 0.326(3) 0.661(2) 0.1523(16) 0.045(10) Uiso 1 1 d . . . . .
C34 C 0.6563(4) 0.4065(3) 0.0850(2) 0.0700(12) Uani 1 1 d . . . . .
C35 C 0.5928(3) 0.3509(2) 0.12364(17) 0.0505(9) Uani 1 1 d . . . . .
C36 C 0.4337(3) 0.33561(19) 0.16982(14) 0.0353(7) Uani 1 1 d . . . . .
C37 C 0.5887(3) 0.2354(2) 0.1760(2) 0.0555(10) Uani 1 1 d . . . . .
H37 H 0.625(3) 0.185(2) 0.1895(16) 0.054(11) Uiso 1 1 d . . . . .
C38 C 0.4842(3) 0.2603(2) 0.19167(15) 0.0402(8) Uani 1 1 d . . . . .
C39 C 0.4137(3) 0.21215(18) 0.22639(15) 0.0360(7) Uani 1 1 d . . . . .
C40 C 0.2329(3) 0.2038(2) 0.25735(17) 0.0463(9) Uani 1 1 d . . . . .
H40 H 0.163(3) 0.2283(19) 0.2562(15) 0.042(10) Uiso 1 1 d . . . . .
C41 C 0.3733(4) 0.0984(2) 0.2767(2) 0.0635(12) Uani 1 1 d . . . . .
H41 H 0.393(4) 0.043(3) 0.2946(19) 0.083(14) Uiso 1 1 d . . . . .
C42 C 0.2629(4) 0.1273(2) 0.2804(2) 0.0622(12) Uani 1 1 d . . . . .
H42 H 0.210(4) 0.097(3) 0.2983(19) 0.086(15) Uiso 1 1 d . . . . .
F1 F 0.6751(19) 0.4779(6) 0.1087(8) 0.118(7) Uani 0.55(3) 1 d . . P A 1
F2 F 0.7603(15) 0.3778(9) 0.0786(13) 0.135(9) Uani 0.62(3) 1 d . . P A 1
F3 F 0.5979(19) 0.416(2) 0.0337(5) 0.141(8) Uani 0.62(5) 1 d . . P A 1
F4 F 0.075(3) 0.1065(9) 0.078(2) 0.143(16) Uani 0.32(4) 1 d . . P B 1
F6 F 0.0584(6) 0.1222(3) 0.0079(3) 0.183(3) Uani 0.977(14) 1 d . U . B 1
F1A F 0.739(3) 0.445(3) 0.1110(8) 0.191(14) Uani 0.45(3) 1 d . . P A 2
F2A F 0.680(5) 0.3593(13) 0.0401(12) 0.159(12) Uani 0.38(3) 1 d . . P A 2
F3A F 0.5885(18) 0.461(3) 0.053(2) 0.137(15) Uani 0.38(5) 1 d . . P A 2
F4A F -0.004(3) 0.1215(12) 0.0939(5) 0.189(10) Uani 0.68(4) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 O1 2.195(2) . ?
Ir1 O2 2.207(2) . ?
Ir1 N5 2.044(2) . ?
Ir1 N8 2.043(2) . ?
Ir1 C27 1.959(3) . ?
Ir1 C36 1.962(3) . ?
P1 O1 1.522(2) . ?
P1 N1 1.584(3) . ?
P1 C1 1.794(3) . ?
P1 C7 1.817(4) . ?
P2 O2 1.514(2) . ?
P2 N1 1.579(3) . ?
P2 C13 1.795(3) . ?
P2 C19 1.803(3) . ?
F5 C25 1.275(8) . ?
N2 C35 1.305(5) . ?
N2 C37 1.350(5) . ?
N3 C35 1.337(5) . ?
N3 C36 1.352(4) . ?
N4 C39 1.329(4) . ?
N4 C41 1.338(5) . ?
N5 C39 1.353(4) . ?
N5 C40 1.341(4) . ?
N6 C26 1.333(4) . ?
N6 C27 1.344(4) . ?
N7 C26 1.316(5) . ?
N7 C28 1.341(5) . ?
N8 C30 1.362(4) . ?
N8 C31 1.334(4) . ?
N9 C30 1.324(4) . ?
N9 C32 1.328(5) . ?
C1 C2 1.374(6) . ?
C1 C6 1.391(6) . ?
C2 C3 1.410(7) . ?
C3 C4 1.349(10) . ?
C4 C5 1.349(10) . ?
C5 C6 1.374(7) . ?
C7 C8 1.378(5) . ?
C7 C12 1.375(5) . ?
C8 C9 1.385(6) . ?
C9 C10 1.350(7) . ?
C10 C11 1.358(6) . ?
C11 C12 1.374(6) . ?
C13 C14 1.384(5) . ?
C13 C18 1.377(5) . ?
C14 C15 1.377(7) . ?
C15 C16 1.362(8) . ?
C16 C17 1.375(8) . ?
C17 C18 1.387(6) . ?
C19 C20 1.383(5) . ?
C19 C24 1.392(5) . ?
C20 C21 1.408(6) . ?
C21 C22 1.376(8) . ?
C22 C23 1.352(8) . ?
C23 C24 1.361(7) . ?
C25 C26 1.529(6) . ?
C25 F4 1.265(19) . ?
C25 F6 1.274(9) . ?
C25 F4A 1.260(10) . ?
C27 C29 1.415(5) . ?
C28 C29 1.368(5) . ?
C29 C30 1.462(5) . ?
C31 C33 1.374(5) . ?
C32 C33 1.374(6) . ?
C34 C35 1.531(6) . ?
C34 F1 1.285(10) . ?
C34 F2 1.317(9) . ?
C34 F3 1.247(14) . ?
C34 F1A 1.200(13) . ?
C34 F2A 1.342(17) . ?
C34 F3A 1.315(18) . ?
C36 C38 1.414(4) . ?
C37 C38 1.373(5) . ?
C38 C39 1.454(4) . ?
C40 C42 1.375(5) . ?
C41 C42 1.371(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ir1 O2 90.66(8) . . ?
N5 Ir1 O1 90.08(9) . . ?
N5 Ir1 O2 93.70(9) . . ?
N8 Ir1 O1 93.68(9) . . ?
N8 Ir1 O2 91.15(9) . . ?
N8 Ir1 N5 173.83(10) . . ?
C27 Ir1 O1 172.88(11) . . ?
C27 Ir1 O2 84.56(11) . . ?
C27 Ir1 N5 95.48(12) . . ?
C27 Ir1 N8 81.17(12) . . ?
C27 Ir1 C36 94.80(13) . . ?
C36 Ir1 O1 90.45(11) . . ?
C36 Ir1 O2 174.52(10) . . ?
C36 Ir1 N5 80.93(12) . . ?
C36 Ir1 N8 94.14(12) . . ?
O1 P1 N1 118.75(14) . . ?
O1 P1 C1 108.21(17) . . ?
O1 P1 C7 108.69(14) . . ?
N1 P1 C1 106.98(17) . . ?
N1 P1 C7 107.25(17) . . ?
C1 P1 C7 106.30(15) . . ?
O2 P2 N1 117.52(14) . . ?
O2 P2 C13 109.00(14) . . ?
O2 P2 C19 109.03(15) . . ?
N1 P2 C13 107.71(17) . . ?
N1 P2 C19 108.72(17) . . ?
C13 P2 C19 104.01(15) . . ?
P1 O1 Ir1 124.72(12) . . ?
P2 O2 Ir1 123.43(12) . . ?
P2 N1 P1 126.5(2) . . ?
C35 N2 C37 114.4(3) . . ?
C35 N3 C36 115.5(3) . . ?
C39 N4 C41 116.7(3) . . ?
C39 N5 Ir1 115.0(2) . . ?
C40 N5 Ir1 126.8(2) . . ?
C40 N5 C39 118.2(3) . . ?
C26 N6 C27 115.6(3) . . ?
C26 N7 C28 114.4(3) . . ?
C30 N8 Ir1 115.4(2) . . ?
C31 N8 Ir1 126.9(2) . . ?
C31 N8 C30 117.7(3) . . ?
C30 N9 C32 116.7(3) . . ?
C2 C1 P1 120.7(3) . . ?
C2 C1 C6 119.2(4) . . ?
C6 C1 P1 120.1(3) . . ?
C1 C2 C3 119.6(6) . . ?
C4 C3 C2 119.8(7) . . ?
C3 C4 C5 120.6(5) . . ?
C4 C5 C6 121.2(6) . . ?
C5 C6 C1 119.6(5) . . ?
C8 C7 P1 121.0(3) . . ?
C12 C7 P1 120.8(3) . . ?
C12 C7 C8 118.1(4) . . ?
C7 C8 C9 120.3(5) . . ?
C10 C9 C8 120.7(5) . . ?
C9 C10 C11 119.4(5) . . ?
C10 C11 C12 121.0(5) . . ?
C11 C12 C7 120.5(4) . . ?
C14 C13 P2 120.2(3) . . ?
C18 C13 P2 120.8(3) . . ?
C18 C13 C14 118.9(4) . . ?
C15 C14 C13 120.4(5) . . ?
C16 C15 C14 119.8(5) . . ?
C15 C16 C17 121.2(5) . . ?
C16 C17 C18 118.7(5) . . ?
C13 C18 C17 120.9(5) . . ?
C20 C19 P2 121.1(3) . . ?
C20 C19 C24 119.1(4) . . ?
C24 C19 P2 119.8(3) . . ?
C19 C20 C21 118.8(4) . . ?
C22 C21 C20 119.1(5) . . ?
C23 C22 C21 122.5(5) . . ?
C22 C23 C24 118.4(5) . . ?
C23 C24 C19 122.0(5) . . ?
F5 C25 C26 112.2(6) . . ?
F4 C25 F5 133.4(15) . . ?
F4 C25 C26 111.4(9) . . ?
F4 C25 F6 77(2) . . ?
F6 C25 F5 101.8(5) . . ?
F6 C25 C26 110.7(6) . . ?
F4A C25 F5 96.8(14) . . ?
F4A C25 C26 114.4(6) . . ?
N6 C26 C25 113.8(4) . . ?
N7 C26 N6 129.9(4) . . ?
N7 C26 C25 116.3(4) . . ?
N6 C27 Ir1 125.8(2) . . ?
N6 C27 C29 119.2(3) . . ?
C29 C27 Ir1 114.6(2) . . ?
N7 C28 C29 122.0(4) . . ?
C27 C29 C30 115.4(3) . . ?
C28 C29 C27 118.8(3) . . ?
C28 C29 C30 125.7(3) . . ?
N8 C30 C29 113.0(3) . . ?
N9 C30 N8 124.6(3) . . ?
N9 C30 C29 122.3(3) . . ?
N8 C31 C33 120.5(3) . . ?
N9 C32 C33 122.5(4) . . ?
C31 C33 C32 118.0(4) . . ?
F1 C34 C35 111.3(6) . . ?
F1 C34 F2 106.2(13) . . ?
F2 C34 C35 112.6(5) . . ?
F3 C34 C35 111.8(7) . . ?
F3 C34 F1 107.4(17) . . ?
F3 C34 F2 107.1(17) . . ?
F1A C34 C35 116.4(8) . . ?
F1A C34 F2A 115(3) . . ?
F1A C34 F3A 105(3) . . ?
F2A C34 C35 105.8(10) . . ?
F3A C34 C35 114.8(7) . . ?
F3A C34 F2A 98(3) . . ?
N2 C35 N3 130.5(4) . . ?
N2 C35 C34 115.9(4) . . ?
N3 C35 C34 113.6(4) . . ?
N3 C36 Ir1 126.7(2) . . ?
N3 C36 C38 118.6(3) . . ?
C38 C36 Ir1 114.6(2) . . ?
N2 C37 C38 121.4(4) . . ?
C36 C38 C39 115.2(3) . . ?
C37 C38 C36 119.5(3) . . ?
C37 C38 C39 125.1(3) . . ?
N4 C39 N5 124.2(3) . . ?
N4 C39 C38 122.1(3) . . ?
N5 C39 C38 113.7(3) . . ?
N5 C40 C42 120.4(3) . . ?
N4 C41 C42 122.7(4) . . ?
C41 C42 C40 117.7(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hb
_database_code_depnum_ccdc_archive 'CCDC 1584486'
_audit_update_record             
;
2018-02-27 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H26 F8 Ir N9 O2 P2'
_chemical_formula_sum            'C42 H26 F8 Ir N9 O2 P2'
_chemical_formula_weight         1094.9

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c  '
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.479(3)
_cell_length_b                   15.111(4)
_cell_length_c                   24.778(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.796(5)
_cell_angle_gamma                90.00
_cell_volume                     4258(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7326
_cell_measurement_theta_min      2.241
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2144
_exptl_absorpt_coefficient_mu    3.295
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28582
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.49
_reflns_number_total             9712
_reflns_number_gt                7296
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0418P)²+4.5544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9712
_refine_ls_number_parameters     577
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.305699(15) 0.767441(13) 0.232921(7) 0.03962(7) Uani 1 1 d . . .
P1 P 0.16675(12) 0.62113(9) 0.15026(6) 0.0482(3) Uani 1 1 d . . .
P2 P 0.14475(12) 0.79625(9) 0.11396(5) 0.0481(3) Uani 1 1 d . . .
N8 N 0.4537(3) 0.8017(3) 0.20010(15) 0.0425(9) Uani 1 1 d . . .
N2 N 0.5038(3) 0.6841(3) 0.30325(16) 0.0479(10) Uani 1 1 d . . .
F4 F 0.6610(4) 0.7404(3) 0.1130(2) 0.1046(15) Uani 1 1 d . . .
C8 C 0.4439(4) 0.9226(3) 0.2592(2) 0.0472(12) Uani 1 1 d . . .
N4 N 0.3053(4) 0.8997(3) 0.32101(17) 0.0501(10) Uani 1 1 d . . .
C10 C 0.3491(4) 0.8747(3) 0.27581(19) 0.0436(11) Uani 1 1 d . . .
N6 N 0.1209(4) 0.6934(3) 0.3599(2) 0.0657(13) Uani 1 1 d . . .
C12 C 0.0215(5) 0.8616(4) 0.0840(2) 0.0513(12) Uani 1 1 d . . .
C13 C 0.0721(4) 0.5804(3) 0.1969(2) 0.0479(12) Uani 1 1 d . . .
C14 C 0.2579(5) 0.8075(4) 0.0709(2) 0.0544(13) Uani 1 1 d . . .
C15 C 0.3165(4) 0.6741(3) 0.3338(2) 0.0465(11) Uani 1 1 d . . .
C16 C 0.5003(4) 0.8810(3) 0.2166(2) 0.0486(12) Uani 1 1 d . . .
C17 C 0.5414(5) 0.6398(4) 0.3487(2) 0.0546(13) Uani 1 1 d . . .
N3 N 0.4327(4) 1.0260(3) 0.3310(2) 0.0658(13) Uani 1 1 d . . .
C19 C -0.0453(5) 0.6048(4) 0.1932(3) 0.0651(15) Uani 1 1 d . . .
H19 H -0.0774 0.6431 0.1657 0.078 Uiso 1 1 calc R . .
N9 N 0.5939(4) 0.9164(3) 0.1995(2) 0.0700(14) Uani 1 1 d . . .
C21 C 0.3513(5) 0.9718(3) 0.3452(2) 0.0523(13) Uani 1 1 d . . .
C22 C 0.5079(5) 0.7540(3) 0.1656(2) 0.0551(14) Uani 1 1 d . . .
H22 H 0.4789 0.6989 0.1538 0.066 Uiso 1 1 calc R . .
C23 C 0.3324(5) 0.8797(4) 0.0756(3) 0.0715(17) Uani 1 1 d . . .
H23 H 0.3202 0.9239 0.1004 0.086 Uiso 1 1 calc R . .
C24 C -0.0821(6) 0.8212(5) 0.0617(3) 0.083(2) Uani 1 1 d . . .
H24 H -0.0881 0.7598 0.0620 0.100 Uiso 1 1 calc R . .
C25 C 0.4784(5) 0.9993(4) 0.2863(2) 0.0642(15) Uani 1 1 d . . .
H25 H 0.5355 1.0341 0.2734 0.077 Uiso 1 1 calc R . .
C26 C 0.1176(5) 0.5251(4) 0.2389(2) 0.0609(14) Uani 1 1 d . . .
H26 H 0.1963 0.5085 0.2424 0.073 Uiso 1 1 calc R . .
C27 C 0.0464(7) 0.4942(4) 0.2758(3) 0.0801(19) Uani 1 1 d . . .
H27 H 0.0775 0.4572 0.3042 0.096 Uiso 1 1 calc R . .
C28 C 0.6059(5) 0.7872(4) 0.1480(3) 0.0665(16) Uani 1 1 d . . .
C29 C 0.6736(6) 0.6289(5) 0.3598(3) 0.080(2) Uani 1 1 d . . .
C30 C 0.1879(5) 0.5285(3) 0.1072(2) 0.0569(14) Uani 1 1 d D . .
N1 N 0.4816(5) 0.6077(3) 0.3860(2) 0.0705(14) Uani 1 1 d . . .
C33 C -0.0697(6) 0.5181(5) 0.2705(3) 0.0777(19) Uani 1 1 d . . .
H33 H -0.1175 0.4966 0.2950 0.093 Uiso 1 1 calc R . .
F1 F 0.7140(4) 0.6076(4) 0.40897(19) 0.1329(19) Uani 1 1 d . . .
C36 C 0.0263(5) 0.9522(4) 0.0826(2) 0.0690(16) Uani 1 1 d . . .
H36 H 0.0951 0.9810 0.0970 0.083 Uiso 1 1 calc R . .
C37 C 0.2140(10) 0.3889(6) 0.0381(4) 0.122(3) Uani 1 1 d . . .
H37 H 0.2238 0.3404 0.0161 0.146 Uiso 1 1 calc R . .
C38 C -0.0705(7) 1.0017(5) 0.0598(3) 0.085(2) Uani 1 1 d . . .
H38 H -0.0665 1.0632 0.0596 0.102 Uiso 1 1 calc R . .
C41 C 0.2939(7) 0.5057(5) 0.0949(3) 0.098(2) Uani 1 1 d . . .
H41 H 0.3599 0.5377 0.1095 0.118 Uiso 1 1 calc R . .
C42 C 0.4438(8) 0.8258(8) 0.0111(4) 0.117(3) Uani 1 1 d . . .
H42 H 0.5060 0.8317 -0.0091 0.141 Uiso 1 1 calc R . .
C43 C 0.6454(6) 0.8694(5) 0.1647(3) 0.0773(19) Uani 1 1 d . . .
H43 H 0.7105 0.8929 0.1510 0.093 Uiso 1 1 calc R . .
F2 F 0.7310(4) 0.6876(5) 0.3426(4) 0.224(5) Uani 1 1 d . . .
C46 C 0.4229(6) 0.8893(6) 0.0458(3) 0.088(2) Uani 1 1 d . . .
H46 H 0.4698 0.9397 0.0497 0.106 Uiso 1 1 calc R . .
C47 C 0.0920(5) 0.4820(6) 0.0822(4) 0.122(3) Uani 1 1 d D . .
H47 H 0.0168 0.4973 0.0890 0.146 Uiso 1 1 calc R . .
C48 C -0.1148(5) 0.5725(4) 0.2302(3) 0.0746(18) Uani 1 1 d . . .
H48 H -0.1937 0.5887 0.2271 0.089 Uiso 1 1 calc R . .
C49 C 0.3063(8) 0.4343(7) 0.0603(4) 0.138(4) Uani 1 1 d . . .
H49 H 0.3808 0.4186 0.0528 0.165 Uiso 1 1 calc R . .
O2 O 0.1923(3) 0.8384(2) 0.16833(13) 0.0496(8) Uani 1 1 d . . .
O1 O 0.2853(3) 0.6464(2) 0.18233(14) 0.0471(8) Uani 1 1 d . . .
N7 N 0.1677(3) 0.7461(3) 0.27515(17) 0.0443(10) Uani 1 1 d . . .
F8 F -0.1269(3) 0.8053(3) 0.2870(2) 0.1070(15) Uani 1 1 d . . .
N5 N 0.0985(4) 0.6976(3) 0.1148(2) 0.0620(12) Uani 1 1 d . . .
C55 C 0.3880(4) 0.7016(3) 0.29457(19) 0.0421(11) Uani 1 1 d . . .
C56 C 0.1952(4) 0.7044(3) 0.3240(2) 0.0480(12) Uani 1 1 d . . .
C57 C -0.0187(5) 0.7711(4) 0.2998(3) 0.0691(17) Uani 1 1 d . . .
C58 C 0.0133(6) 0.7273(4) 0.3476(3) 0.0753(19) Uani 1 1 d . . .
H58 H -0.0408 0.7209 0.3720 0.090 Uiso 1 1 calc R . .
C59 C 0.0601(5) 0.7809(3) 0.2636(3) 0.0576(14) Uani 1 1 d . . .
H59 H 0.0391 0.8114 0.2311 0.069 Uiso 1 1 calc R . .
C60 C 0.3656(5) 0.6257(4) 0.3772(2) 0.0661(16) Uani 1 1 d . . .
H60 H 0.3176 0.6043 0.4016 0.079 Uiso 1 1 calc R . .
F7 F 0.2728(7) 1.0708(4) 0.4030(2) 0.181(3) Uani 1 1 d . . .
C62 C 0.2803(8) 0.7425(5) 0.0348(3) 0.093(2) Uani 1 1 d . . .
H62 H 0.2333 0.6923 0.0300 0.112 Uiso 1 1 calc R . .
C63 C 0.3110(7) 0.9936(5) 0.3989(3) 0.0740(17) Uani 1 1 d . . .
F5 F 0.2200(6) 0.9493(4) 0.4090(2) 0.175(3) Uani 1 1 d . . .
F6 F 0.3851(5) 0.9795(7) 0.43816(19) 0.227(5) Uani 1 1 d . . .
C66 C -0.1703(6) 0.9603(6) 0.0378(3) 0.083(2) Uani 1 1 d . . .
H66 H -0.2342 0.9934 0.0220 0.100 Uiso 1 1 calc R . .
C67 C -0.1778(6) 0.8721(6) 0.0387(3) 0.100(2) Uani 1 1 d . . .
H67 H -0.2472 0.8444 0.0239 0.119 Uiso 1 1 calc R . .
C68 C 0.3756(11) 0.7534(8) 0.0051(4) 0.130(4) Uani 1 1 d . . .
H68 H 0.3916 0.7095 -0.0191 0.156 Uiso 1 1 calc R . .
C69 C 0.1068(10) 0.4127(7) 0.0472(4) 0.145(4) Uani 1 1 d . . .
H69 H 0.0415 0.3826 0.0299 0.174 Uiso 1 1 calc R . .
F3 F 0.7021(4) 0.5562(5) 0.3331(2) 0.159(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 C55 1.956(5) . ?
Ir1 C10 1.965(5) . ?
Ir1 N7 2.039(4) . ?
Ir1 N8 2.046(4) . ?
Ir1 O2 2.200(3) . ?
Ir1 O1 2.212(3) . ?
P1 O1 1.529(3) . ?
P1 N5 1.593(5) . ?
P1 C30 1.796(5) . ?
P1 C13 1.799(5) . ?
P2 O2 1.523(3) . ?
P2 N5 1.583(5) . ?
P2 C14 1.798(6) . ?
P2 C12 1.801(5) . ?
N8 C22 1.334(7) . ?
N8 C16 1.353(6) . ?
N2 C17 1.331(6) . ?
N2 C55 1.344(6) . ?
F4 C28 1.343(7) . ?
C8 C25 1.369(7) . ?
C8 C10 1.414(6) . ?
C8 C16 1.454(7) . ?
N4 C21 1.319(6) . ?
N4 C10 1.342(6) . ?
N6 C56 1.323(6) . ?
N6 C58 1.334(8) . ?
C12 C36 1.371(8) . ?
C12 C24 1.383(8) . ?
C13 C26 1.380(7) . ?
C13 C19 1.389(7) . ?
C14 C62 1.376(9) . ?
C14 C23 1.381(8) . ?
C15 C60 1.358(7) . ?
C15 C55 1.417(6) . ?
C15 C56 1.455(7) . ?
C16 N9 1.321(6) . ?
C17 N1 1.317(7) . ?
C17 C29 1.514(8) . ?
N3 C21 1.326(7) . ?
N3 C25 1.350(7) . ?
C19 C48 1.383(8) . ?
C19 H19 0.9300 . ?
N9 C43 1.319(8) . ?
C21 C63 1.503(8) . ?
C22 C28 1.356(8) . ?
C22 H22 0.9300 . ?
C23 C46 1.362(9) . ?
C23 H23 0.9300 . ?
C24 C67 1.399(9) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.388(8) . ?
C26 H26 0.9300 . ?
C27 C33 1.370(9) . ?
C27 H27 0.9300 . ?
C28 C43 1.367(9) . ?
C29 F2 1.215(8) . ?
C29 F1 1.284(7) . ?
C29 F3 1.346(9) . ?
C30 C41 1.339(8) . ?
C30 C47 1.3798(11) . ?
N1 C60 1.347(7) . ?
C33 C48 1.343(9) . ?
C33 H33 0.9300 . ?
C36 C38 1.394(8) . ?
C36 H36 0.9300 . ?
C37 C49 1.319(12) . ?
C37 C69 1.329(12) . ?
C37 H37 0.9300 . ?
C38 C66 1.354(10) . ?
C38 H38 0.9300 . ?
C41 C49 1.396(10) . ?
C41 H41 0.9300 . ?
C42 C46 1.332(12) . ?
C42 C68 1.341(13) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C46 H46 0.9300 . ?
C47 C69 1.386(11) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
N7 C59 1.337(7) . ?
N7 C56 1.362(6) . ?
F8 C57 1.343(7) . ?
C57 C58 1.362(10) . ?
C57 C59 1.367(8) . ?
C58 H58 0.9300 . ?
C59 H59 0.9300 . ?
C60 H60 0.9300 . ?
F7 C63 1.256(8) . ?
C62 C68 1.408(12) . ?
C62 H62 0.9300 . ?
C63 F6 1.221(8) . ?
C63 F5 1.293(8) . ?
C66 C67 1.335(10) . ?
C66 H66 0.9300 . ?
C67 H67 0.9300 . ?
C68 H68 0.9300 . ?
C69 H69 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
C55 Ir1 C10 86.40(19) . . ?
C55 Ir1 N7 81.12(18) . . ?
C10 Ir1 N7 90.58(18) . . ?
C55 Ir1 N8 95.73(17) . . ?
C10 Ir1 N8 80.99(18) . . ?
N7 Ir1 N8 171.20(16) . . ?
C55 Ir1 O2 172.59(16) . . ?
C10 Ir1 O2 94.18(16) . . ?
N7 Ir1 O2 91.48(15) . . ?
N8 Ir1 O2 91.66(14) . . ?
C55 Ir1 O1 91.40(16) . . ?
C10 Ir1 O1 171.20(16) . . ?
N7 Ir1 O1 97.50(14) . . ?
N8 Ir1 O1 90.77(14) . . ?
O2 Ir1 O1 89.10(12) . . ?
O1 P1 N5 116.3(2) . . ?
O1 P1 C30 108.7(2) . . ?
N5 P1 C30 109.5(3) . . ?
O1 P1 C13 108.9(2) . . ?
N5 P1 C13 108.0(3) . . ?
C30 P1 C13 104.9(2) . . ?
O2 P2 N5 117.6(2) . . ?
O2 P2 C14 106.5(2) . . ?
N5 P2 C14 111.6(3) . . ?
O2 P2 C12 107.6(2) . . ?
N5 P2 C12 106.0(3) . . ?
C14 P2 C12 107.1(2) . . ?
C22 N8 C16 118.1(4) . . ?
C22 N8 Ir1 127.1(4) . . ?
C16 N8 Ir1 114.8(3) . . ?
C17 N2 C55 115.8(4) . . ?
C25 C8 C10 118.3(5) . . ?
C25 C8 C16 126.4(5) . . ?
C10 C8 C16 115.2(4) . . ?
C21 N4 C10 116.0(4) . . ?
N4 C10 C8 119.3(4) . . ?
N4 C10 Ir1 125.9(4) . . ?
C8 C10 Ir1 114.4(4) . . ?
C56 N6 C58 117.4(5) . . ?
C36 C12 C24 117.8(5) . . ?
C36 C12 P2 121.7(4) . . ?
C24 C12 P2 120.5(5) . . ?
C26 C13 C19 118.4(5) . . ?
C26 C13 P1 119.4(4) . . ?
C19 C13 P1 122.1(4) . . ?
C62 C14 C23 116.8(6) . . ?
C62 C14 P2 122.2(5) . . ?
C23 C14 P2 120.9(5) . . ?
C60 C15 C55 119.0(5) . . ?
C60 C15 C56 125.9(5) . . ?
C55 C15 C56 115.1(4) . . ?
N9 C16 N8 124.6(5) . . ?
N9 C16 C8 121.3(5) . . ?
N8 C16 C8 114.0(4) . . ?
N1 C17 N2 129.7(5) . . ?
N1 C17 C29 116.0(5) . . ?
N2 C17 C29 114.2(5) . . ?
C21 N3 C25 113.5(5) . . ?
C48 C19 C13 120.3(6) . . ?
C48 C19 H19 119.9 . . ?
C13 C19 H19 119.9 . . ?
C43 N9 C16 116.7(5) . . ?
N4 C21 N3 130.0(5) . . ?
N4 C21 C63 115.5(5) . . ?
N3 C21 C63 114.4(5) . . ?
N8 C22 C28 119.1(5) . . ?
N8 C22 H22 120.5 . . ?
C28 C22 H22 120.5 . . ?
C46 C23 C14 123.1(7) . . ?
C46 C23 H23 118.4 . . ?
C14 C23 H23 118.4 . . ?
C12 C24 C67 120.3(7) . . ?
C12 C24 H24 119.8 . . ?
C67 C24 H24 119.8 . . ?
N3 C25 C8 122.4(5) . . ?
N3 C25 H25 118.8 . . ?
C8 C25 H25 118.8 . . ?
C13 C26 C27 120.3(6) . . ?
C13 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C33 C27 C26 120.0(6) . . ?
C33 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
F4 C28 C22 119.8(6) . . ?
F4 C28 C43 120.5(5) . . ?
C22 C28 C43 119.7(6) . . ?
F2 C29 F1 111.8(8) . . ?
F2 C29 F3 104.2(8) . . ?
F1 C29 F3 100.4(6) . . ?
F2 C29 C17 115.7(6) . . ?
F1 C29 C17 115.1(6) . . ?
F3 C29 C17 107.7(6) . . ?
C41 C30 C47 117.4(6) . . ?
C41 C30 P1 122.5(4) . . ?
C47 C30 P1 120.0(5) . . ?
C17 N1 C60 114.2(5) . . ?
C48 C33 C27 120.3(6) . . ?
C48 C33 H33 119.8 . . ?
C27 C33 H33 119.8 . . ?
C12 C36 C38 120.9(6) . . ?
C12 C36 H36 119.5 . . ?
C38 C36 H36 119.5 . . ?
C49 C37 C69 120.0(9) . . ?
C49 C37 H37 120.0 . . ?
C69 C37 H37 120.0 . . ?
C66 C38 C36 119.9(7) . . ?
C66 C38 H38 120.0 . . ?
C36 C38 H38 120.0 . . ?
C30 C41 C49 120.7(7) . . ?
C30 C41 H41 119.6 . . ?
C49 C41 H41 119.6 . . ?
C46 C42 C68 120.4(9) . . ?
C46 C42 H42 119.8 . . ?
C68 C42 H42 119.8 . . ?
N9 C43 C28 121.7(6) . . ?
N9 C43 H43 119.1 . . ?
C28 C43 H43 119.1 . . ?
C42 C46 C23 119.4(8) . . ?
C42 C46 H46 120.3 . . ?
C23 C46 H46 120.3 . . ?
C30 C47 C69 120.5(7) . . ?
C30 C47 H47 119.7 . . ?
C69 C47 H47 119.7 . . ?
C33 C48 C19 120.7(6) . . ?
C33 C48 H48 119.7 . . ?
C19 C48 H48 119.7 . . ?
C37 C49 C41 120.9(9) . . ?
C37 C49 H49 119.5 . . ?
C41 C49 H49 119.5 . . ?
P2 O2 Ir1 123.05(19) . . ?
P1 O1 Ir1 121.26(18) . . ?
C59 N7 C56 117.9(5) . . ?
C59 N7 Ir1 126.0(4) . . ?
C56 N7 Ir1 115.2(3) . . ?
P2 N5 P1 123.3(3) . . ?
N2 C55 C15 119.0(4) . . ?
N2 C55 Ir1 126.0(3) . . ?
C15 C55 Ir1 114.9(3) . . ?
N6 C56 N7 124.2(5) . . ?
N6 C56 C15 122.5(5) . . ?
N7 C56 C15 113.3(4) . . ?
F8 C57 C58 121.6(6) . . ?
F8 C57 C59 118.5(6) . . ?
C58 C57 C59 119.9(6) . . ?
N6 C58 C57 121.1(6) . . ?
N6 C58 H58 119.4 . . ?
C57 C58 H58 119.4 . . ?
N7 C59 C57 119.4(6) . . ?
N7 C59 H59 120.3 . . ?
C57 C59 H59 120.3 . . ?
N1 C60 C15 122.1(5) . . ?
N1 C60 H60 118.9 . . ?
C15 C60 H60 118.9 . . ?
C14 C62 C68 118.9(8) . . ?
C14 C62 H62 120.6 . . ?
C68 C62 H62 120.6 . . ?
F6 C63 F7 108.0(8) . . ?
F6 C63 F5 104.5(7) . . ?
F7 C63 F5 99.5(7) . . ?
F6 C63 C21 113.8(6) . . ?
F7 C63 C21 115.4(6) . . ?
F5 C63 C21 114.3(6) . . ?
C67 C66 C38 120.5(6) . . ?
C67 C66 H66 119.7 . . ?
C38 C66 H66 119.7 . . ?
C66 C67 C24 120.5(7) . . ?
C66 C67 H67 119.8 . . ?
C24 C67 H67 119.8 . . ?
C42 C68 C62 121.4(9) . . ?
C42 C68 H68 119.3 . . ?
C62 C68 H68 119.3 . . ?
C37 C69 C47 120.3(8) . . ?
C37 C69 H69 119.8 . . ?
C47 C69 H69 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.503
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.096
