# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1033811'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H26 F4 Ir N3 O'
_chemical_formula_sum            'C37 H26 F4 Ir N3 O'
_chemical_formula_weight         796.81

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'
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   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   10.0391(13)
_cell_length_b                   16.249(2)
_cell_length_c                   18.799(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.547(2)
_cell_angle_gamma                90.00
_cell_volume                     3024.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    4.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_T_max  0.639
_exptl_absorpt_process_details   sadabs

_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            24129
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_sigmaI/netI    0.1832
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.10
_diffrn_reflns_theta_max         26.00
_reflns_number_total             11773
_reflns_number_gt                8577
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(8)
_refine_ls_number_reflns         11773
_refine_ls_number_parameters     819
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1547(10) 0.7189(5) 0.2232(5) 0.017(2) Uani 1 1 d . . .
C2 C -0.2254(11) 0.7018(5) 0.2771(6) 0.025(2) Uani 1 1 d . . .
H2 H -0.2814 0.7426 0.2905 0.029 Uiso 1 1 calc R . .
C3 C -0.2189(13) 0.6263(6) 0.3136(6) 0.031(3) Uani 1 1 d . . .
H3 H -0.2669 0.6179 0.3513 0.038 Uiso 1 1 calc R . .
C4 C -0.1399(14) 0.5652(5) 0.2924(6) 0.038(3) Uani 1 1 d . . .
H4 H -0.1378 0.5140 0.3148 0.045 Uiso 1 1 calc R . .
C5 C -0.0640(13) 0.5774(6) 0.2391(6) 0.037(3) Uani 1 1 d . . .
H5 H -0.0096 0.5352 0.2265 0.044 Uiso 1 1 calc R . .
C6 C -0.0683(9) 0.6543(5) 0.2033(4) 0.0176(18) Uani 1 1 d . . .
C7 C 0.0107(9) 0.6609(6) 0.1461(4) 0.0224(18) Uani 1 1 d . . .
H7 H 0.0529 0.6124 0.1358 0.027 Uiso 1 1 calc R . .
C8 C 0.1129(11) 0.7044(6) 0.0480(5) 0.025(2) Uani 1 1 d . . .
H8 H 0.1292 0.7579 0.0269 0.030 Uiso 1 1 calc R . .
C9 C 0.2500(10) 0.6699(6) 0.0781(5) 0.024(2) Uani 1 1 d . . .
C10 C 0.3519(12) 0.7240(6) 0.1111(6) 0.032(3) Uani 1 1 d . . .
H10 H 0.3343 0.7801 0.1116 0.039 Uiso 1 1 calc R . .
C11 C 0.4764(12) 0.6953(7) 0.1426(6) 0.035(3) Uani 1 1 d . . .
H11 H 0.5400 0.7321 0.1660 0.042 Uiso 1 1 calc R . .
C12 C 0.5093(12) 0.6119(7) 0.1401(6) 0.037(3) Uani 1 1 d . . .
H12 H 0.5933 0.5927 0.1623 0.044 Uiso 1 1 calc R . .
C13 C 0.4117(14) 0.5573(6) 0.1030(7) 0.043(3) Uani 1 1 d . . .
H13 H 0.4334 0.5023 0.0972 0.051 Uiso 1 1 calc R . .
C14 C 0.2837(11) 0.5863(5) 0.0752(5) 0.027(2) Uani 1 1 d . . .
H14 H 0.2183 0.5492 0.0541 0.032 Uiso 1 1 calc R . .
C15 C 0.0317(12) 0.6548(7) -0.0117(5) 0.034(2) Uani 1 1 d . . .
H15A H 0.0836 0.6468 -0.0497 0.050 Uiso 1 1 calc R . .
H15B H -0.0501 0.6837 -0.0302 0.050 Uiso 1 1 calc R . .
H15C H 0.0099 0.6023 0.0067 0.050 Uiso 1 1 calc R . .
C16 C 0.1956(12) 0.8285(6) 0.2338(5) 0.027(2) Uani 1 1 d . . .
H16 H 0.2047 0.7767 0.2140 0.032 Uiso 1 1 calc R . .
C17 C 0.2911(12) 0.8541(7) 0.2899(6) 0.035(3) Uani 1 1 d . . .
H17 H 0.3652 0.8211 0.3069 0.042 Uiso 1 1 calc R . .
C18 C 0.2755(13) 0.9311(6) 0.3213(6) 0.038(3) Uani 1 1 d . . .
H18 H 0.3402 0.9512 0.3584 0.046 Uiso 1 1 calc R . .
C19 C 0.1591(13) 0.9765(6) 0.2949(6) 0.040(3) Uani 1 1 d . . .
H19 H 0.1428 1.0256 0.3174 0.048 Uiso 1 1 calc R . .
C20 C 0.0702(11) 0.9503(5) 0.2375(5) 0.024(2) Uani 1 1 d . . .
C21 C -0.0521(11) 0.9944(5) 0.1993(5) 0.023(2) Uani 1 1 d . . .
C22 C -0.0968(13) 1.0692(5) 0.2214(6) 0.034(3) Uani 1 1 d . . .
C23 C -0.2075(13) 1.1072(5) 0.1852(7) 0.037(3) Uani 1 1 d . . .
H23 H -0.2347 1.1586 0.1991 0.045 Uiso 1 1 calc R . .
C24 C -0.2776(13) 1.0662(5) 0.1271(7) 0.035(3) Uani 1 1 d . . .
C25 C -0.2375(11) 0.9916(5) 0.1026(6) 0.025(2) Uani 1 1 d . . .
H25 H -0.2861 0.9674 0.0616 0.030 Uiso 1 1 calc R . .
C26 C -0.1251(12) 0.9538(5) 0.1398(5) 0.023(2) Uani 1 1 d . . .
C27 C -0.3075(12) 0.7828(6) 0.0322(6) 0.030(3) Uani 1 1 d . . .
H27 H -0.3242 0.7606 0.0755 0.036 Uiso 1 1 calc R . .
C28 C -0.4034(12) 0.7743(6) -0.0302(6) 0.037(3) Uani 1 1 d . . .
H28 H -0.4842 0.7471 -0.0281 0.045 Uiso 1 1 calc R . .
C29 C -0.3805(13) 0.8044(7) -0.0921(7) 0.041(3) Uani 1 1 d . . .
H29 H -0.4455 0.7989 -0.1333 0.049 Uiso 1 1 calc R . .
C30 C -0.2584(11) 0.8448(7) -0.0963(5) 0.033(2) Uani 1 1 d . . .
H30 H -0.2417 0.8654 -0.1401 0.040 Uiso 1 1 calc R . .
C31 C -0.1626(10) 0.8537(6) -0.0343(5) 0.021(2) Uani 1 1 d . . .
C32 C -0.0307(11) 0.8923(4) -0.0257(6) 0.026(2) Uani 1 1 d . . .
C33 C 0.0315(13) 0.9213(5) -0.0814(6) 0.037(3) Uani 1 1 d . . .
C34 C 0.1609(13) 0.9571(6) -0.0708(6) 0.036(3) Uani 1 1 d . . .
H34 H 0.1996 0.9766 -0.1092 0.043 Uiso 1 1 calc R . .
C35 C 0.2268(12) 0.9616(6) -0.0012(6) 0.032(3) Uani 1 1 d . . .
C36 C 0.1707(12) 0.9327(6) 0.0567(6) 0.028(2) Uani 1 1 d . . .
H36 H 0.2179 0.9383 0.1034 0.034 Uiso 1 1 calc R . .
C37 C 0.0460(11) 0.8960(5) 0.0455(5) 0.020(2) Uani 1 1 d . . .
C38 C 0.3119(11) 0.0699(5) 0.4708(5) 0.017(2) Uani 1 1 d . . .
C39 C 0.2397(10) -0.0011(5) 0.4858(5) 0.016(2) Uani 1 1 d . . .
H39 H 0.2798 -0.0521 0.4815 0.019 Uiso 1 1 calc R . .
C40 C 0.1147(11) 0.0001(5) 0.5062(6) 0.026(2) Uani 1 1 d . . .
H40 H 0.0699 -0.0487 0.5129 0.031 Uiso 1 1 calc R . .
C41 C 0.0552(10) 0.0771(5) 0.5167(5) 0.022(2) Uani 1 1 d . . .
H41 H -0.0285 0.0793 0.5316 0.026 Uiso 1 1 calc R . .
C42 C 0.1209(10) 0.1485(5) 0.5050(5) 0.027(2) Uani 1 1 d . . .
H42 H 0.0814 0.1988 0.5127 0.032 Uiso 1 1 calc R . .
C43 C 0.2458(10) 0.1473(4) 0.4816(5) 0.0178(19) Uani 1 1 d . . .
C44 C 0.3077(9) 0.2266(5) 0.4794(5) 0.0155(19) Uani 1 1 d . . .
H44 H 0.2664 0.2696 0.5001 0.019 Uiso 1 1 calc R . .
C45 C 0.4615(10) 0.3337(5) 0.4607(4) 0.0176(19) Uani 1 1 d . . .
H45 H 0.5603 0.3325 0.4660 0.021 Uiso 1 1 calc R . .
C46 C 0.4108(9) 0.3836(4) 0.3930(5) 0.0167(19) Uani 1 1 d . . .
C47 C 0.2745(12) 0.3913(5) 0.3668(5) 0.028(2) Uani 1 1 d . . .
H47 H 0.2118 0.3659 0.3908 0.034 Uiso 1 1 calc R . .
C48 C 0.2312(13) 0.4364(6) 0.3054(7) 0.039(3) Uani 1 1 d . . .
H48 H 0.1396 0.4395 0.2865 0.046 Uiso 1 1 calc R . .
C49 C 0.3245(13) 0.4769(6) 0.2719(6) 0.034(3) Uani 1 1 d . . .
H49 H 0.2945 0.5062 0.2299 0.040 Uiso 1 1 calc R . .
C50 C 0.4589(12) 0.4754(5) 0.2984(6) 0.031(2) Uani 1 1 d . . .
H50 H 0.5194 0.5063 0.2770 0.037 Uiso 1 1 calc R . .
C51 C 0.5044(10) 0.4260(5) 0.3589(5) 0.022(2) Uani 1 1 d . . .
H51 H 0.5964 0.4214 0.3764 0.027 Uiso 1 1 calc R . .
C52 C 0.4272(11) 0.3760(5) 0.5278(6) 0.027(2) Uani 1 1 d . . .
H52A H 0.4881 0.4211 0.5409 0.040 Uiso 1 1 calc R . .
H52B H 0.4356 0.3372 0.5669 0.040 Uiso 1 1 calc R . .
H52C H 0.3362 0.3963 0.5179 0.040 Uiso 1 1 calc R . .
C53 C 0.2893(10) 0.1932(5) 0.2879(6) 0.022(2) Uani 1 1 d . . .
H53 H 0.2688 0.2335 0.3196 0.026 Uiso 1 1 calc R . .
C54 C 0.2072(12) 0.1856(6) 0.2221(6) 0.033(3) Uani 1 1 d . . .
H54 H 0.1286 0.2167 0.2115 0.040 Uiso 1 1 calc R . .
C55 C 0.2423(13) 0.1320(6) 0.1725(6) 0.038(3) Uani 1 1 d . . .
H55 H 0.1920 0.1289 0.1263 0.046 Uiso 1 1 calc R . .
C56 C 0.3529(12) 0.0831(6) 0.1921(6) 0.032(3) Uani 1 1 d . . .
H56 H 0.3776 0.0458 0.1592 0.039 Uiso 1 1 calc R . .
C57 C 0.4282(10) 0.0884(5) 0.2600(5) 0.0177(14) Uani 1 1 d . . .
C58 C 0.5469(11) 0.0399(5) 0.2895(5) 0.021(2) Uani 1 1 d . . .
C59 C 0.5917(11) -0.0293(5) 0.2569(5) 0.023(2) Uani 1 1 d . . .
C60 C 0.7050(11) -0.0738(5) 0.2856(6) 0.0272(18) Uani 1 1 d . . .
H60 H 0.7316 -0.1206 0.2632 0.033 Uiso 1 1 calc R . .
C61 C 0.7786(12) -0.0436(5) 0.3517(6) 0.028(2) Uani 1 1 d . . .
C62 C 0.7385(11) 0.0225(5) 0.3870(5) 0.024(2) Uani 1 1 d . . .
H62 H 0.7880 0.0392 0.4309 0.028 Uiso 1 1 calc R . .
C63 C 0.6197(11) 0.0659(5) 0.3560(5) 0.019(2) Uani 1 1 d . . .
C64 C 0.6702(12) 0.1367(5) 0.5558(5) 0.022(2) Uani 1 1 d . . .
H64 H 0.6049 0.0968 0.5590 0.027 Uiso 1 1 calc R . .
C65 C 0.7578(10) 0.1565(7) 0.6163(5) 0.028(2) Uani 1 1 d . . .
H65 H 0.7523 0.1305 0.6597 0.034 Uiso 1 1 calc R . .
C66 C 0.8551(10) 0.2154(6) 0.6129(6) 0.025(2) Uani 1 1 d . . .
H66 H 0.9163 0.2298 0.6537 0.030 Uiso 1 1 calc R . .
C67 C 0.8596(10) 0.2526(5) 0.5474(5) 0.018(2) Uani 1 1 d . . .
H67 H 0.9225 0.2939 0.5445 0.022 Uiso 1 1 calc R . .
C68 C 0.7708(10) 0.2290(5) 0.4852(5) 0.0177(14) Uani 1 1 d . . .
C69 C 0.7670(9) 0.2586(4) 0.4120(5) 0.0148(19) Uani 1 1 d . . .
C70 C 0.8668(10) 0.3046(5) 0.3853(6) 0.024(2) Uani 1 1 d . . .
C71 C 0.8549(11) 0.3305(5) 0.3160(6) 0.0272(18) Uani 1 1 d . . .
H71 H 0.9228 0.3614 0.3005 0.033 Uiso 1 1 calc R . .
C72 C 0.7395(12) 0.3098(5) 0.2692(6) 0.028(3) Uani 1 1 d . . .
C73 C 0.6394(12) 0.2616(5) 0.2920(6) 0.026(2) Uani 1 1 d . . .
H73 H 0.5645 0.2470 0.2583 0.031 Uiso 1 1 calc R . .
C74 C 0.6459(11) 0.2350(5) 0.3614(5) 0.023(2) Uani 1 1 d . . .
F1 F -0.0306(8) 1.1080(4) 0.2809(4) 0.049(2) Uani 1 1 d . . .
F2 F -0.3896(8) 1.1041(4) 0.0913(4) 0.050(2) Uani 1 1 d . . .
F3 F -0.0322(8) 0.9151(4) -0.1508(3) 0.0478(18) Uani 1 1 d . . .
F4 F 0.3471(8) 0.9982(4) 0.0107(4) 0.050(2) Uani 1 1 d . . .
F5 F 0.5217(7) -0.0577(3) 0.1938(3) 0.0338(14) Uani 1 1 d . . .
F6 F 0.8901(7) -0.0861(3) 0.3805(4) 0.0415(17) Uani 1 1 d . . .
F7 F 0.9834(6) 0.3221(3) 0.4318(3) 0.0300(14) Uani 1 1 d . . .
F8 F 0.7261(7) 0.3353(4) 0.2007(3) 0.0418(17) Uani 1 1 d . . .
Ir1 Ir -0.05044(4) 0.842522(16) 0.119021(18) 0.01716(9) Uani 1 1 d . . .
Ir2 Ir 0.52895(3) 0.157208(14) 0.402782(18) 0.01403(9) Uani 1 1 d . . .
N1 N 0.0322(8) 0.7218(4) 0.1075(4) 0.0169(16) Uani 1 1 d . . .
N2 N 0.0907(10) 0.8745(4) 0.2065(4) 0.023(2) Uani 1 1 d . . .
N3 N -0.1907(9) 0.8229(4) 0.0302(5) 0.023(2) Uani 1 1 d . . .
N4 N 0.4143(9) 0.2459(4) 0.4522(4) 0.0166(18) Uani 1 1 d . . .
N5 N 0.3983(9) 0.1451(4) 0.3089(4) 0.0191(18) Uani 1 1 d . . .
N6 N 0.6737(9) 0.1722(4) 0.4915(4) 0.0174(18) Uani 1 1 d . . .
O1 O -0.1693(7) 0.7908(3) 0.1910(3) 0.0196(14) Uani 1 1 d . . .
O2 O 0.4242(7) 0.0628(3) 0.4487(4) 0.0171(15) 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
C1 O1 1.313(10) . ?
C1 C2 1.358(14) . ?
C1 C6 1.450(12) . ?
C2 C3 1.403(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.417(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(12) . ?
C7 N1 1.266(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.506(14) . ?
C8 C15 1.507(14) . ?
C8 N1 1.512(12) . ?
C8 H8 0.9800 . ?
C9 C14 1.404(12) . ?
C9 C10 1.411(15) . ?
C10 C11 1.373(16) . ?
C10 H10 0.9300 . ?
C11 C12 1.397(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.417(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(16) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N2 1.324(14) . ?
C16 C17 1.367(15) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(15) . ?
C17 H17 0.9300 . ?
C18 C19 1.402(18) . ?
C18 H18 0.9300 . ?
C19 C20 1.351(15) . ?
C19 H19 0.9300 . ?
C20 N2 1.393(11) . ?
C20 C21 1.497(15) . ?
C21 C22 1.383(12) . ?
C21 C26 1.397(14) . ?
C22 C23 1.352(18) . ?
C22 F1 1.358(13) . ?
C23 C24 1.370(17) . ?
C23 H23 0.9300 . ?
C24 F2 1.359(14) . ?
C24 C25 1.380(13) . ?
C25 C26 1.371(15) . ?
C25 H25 0.9300 . ?
C26 Ir1 2.019(9) . ?
C27 N3 1.348(14) . ?
C27 C28 1.397(16) . ?
C27 H27 0.9300 . ?
C28 C29 1.317(16) . ?
C28 H28 0.9300 . ?
C29 C30 1.404(16) . ?
C29 H29 0.9300 . ?
C30 C31 1.390(14) . ?
C30 H30 0.9300 . ?
C31 N3 1.383(13) . ?
C31 C32 1.449(14) . ?
C32 C33 1.388(14) . ?
C32 C37 1.430(14) . ?
C33 F3 1.357(12) . ?
C33 C34 1.406(17) . ?
C34 C35 1.367(16) . ?
C34 H34 0.9300 . ?
C35 F4 1.331(12) . ?
C35 C36 1.387(15) . ?
C36 C37 1.371(15) . ?
C36 H36 0.9300 . ?
C37 Ir1 2.012(9) . ?
C38 O2 1.270(12) . ?
C38 C39 1.416(12) . ?
C38 C43 1.452(11) . ?
C39 C40 1.372(14) . ?
C39 H39 0.9300 . ?
C40 C41 1.415(12) . ?
C40 H40 0.9300 . ?
C41 C42 1.369(13) . ?
C41 H41 0.9300 . ?
C42 C43 1.396(13) . ?
C42 H42 0.9300 . ?
C43 C44 1.434(11) . ?
C44 N4 1.299(12) . ?
C44 H44 0.9300 . ?
C45 N4 1.502(10) . ?
C45 C46 1.525(11) . ?
C45 C52 1.525(12) . ?
C45 H45 0.9800 . ?
C46 C47 1.380(14) . ?
C46 C51 1.402(13) . ?
C47 C48 1.376(14) . ?
C47 H47 0.9300 . ?
C48 C49 1.379(16) . ?
C48 H48 0.9300 . ?
C49 C50 1.358(16) . ?
C49 H49 0.9300 . ?
C50 C51 1.406(14) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 N5 1.349(12) . ?
C53 C54 1.374(15) . ?
C53 H53 0.9300 . ?
C54 C55 1.365(15) . ?
C54 H54 0.9300 . ?
C55 C56 1.366(16) . ?
C55 H55 0.9300 . ?
C56 C57 1.373(14) . ?
C56 H56 0.9300 . ?
C57 N5 1.369(11) . ?
C57 C58 1.460(13) . ?
C58 C59 1.391(12) . ?
C58 C63 1.405(14) . ?
C59 F5 1.356(10) . ?
C59 C60 1.380(15) . ?
C60 C61 1.422(15) . ?
C60 H60 0.9300 . ?
C61 F6 1.350(13) . ?
C61 C62 1.360(12) . ?
C62 C63 1.424(14) . ?
C62 H62 0.9300 . ?
C63 Ir2 2.018(9) . ?
C64 N6 1.346(12) . ?
C64 C65 1.355(14) . ?
C64 H64 0.9300 . ?
C65 C66 1.376(15) . ?
C65 H65 0.9300 . ?
C66 C67 1.378(14) . ?
C66 H66 0.9300 . ?
C67 C68 1.401(13) . ?
C67 H67 0.9300 . ?
C68 N6 1.363(12) . ?
C68 C69 1.451(13) . ?
C69 C70 1.407(13) . ?
C69 C74 1.465(14) . ?
C70 C71 1.357(14) . ?
C70 F7 1.369(12) . ?
C71 C72 1.376(16) . ?
C71 H71 0.9300 . ?
C72 F8 1.338(12) . ?
C72 C73 1.396(15) . ?
C73 C74 1.367(14) . ?
C73 H73 0.9300 . ?
C74 Ir2 1.970(10) . ?
Ir1 N3 2.023(9) . ?
Ir1 N2 2.052(8) . ?
Ir1 O1 2.120(6) . ?
Ir1 N1 2.155(6) . ?
Ir2 N5 2.027(8) . ?
Ir2 N6 2.037(9) . ?
Ir2 O2 2.123(6) . ?
Ir2 N4 2.149(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 119.6(8) . . ?
O1 C1 C6 123.4(8) . . ?
C2 C1 C6 117.0(7) . . ?
C1 C2 C3 123.8(9) . . ?
C1 C2 H2 118.1 . . ?
C3 C2 H2 118.1 . . ?
C4 C3 C2 118.2(10) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 121.8(9) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 119.9(9) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 116.3(8) . . ?
C5 C6 C1 119.3(8) . . ?
C7 C6 C1 124.4(8) . . ?
N1 C7 C6 130.8(9) . . ?
N1 C7 H7 114.6 . . ?
C6 C7 H7 114.6 . . ?
C9 C8 C15 115.4(8) . . ?
C9 C8 N1 111.1(8) . . ?
C15 C8 N1 111.1(8) . . ?
C9 C8 H8 106.2 . . ?
C15 C8 H8 106.2 . . ?
N1 C8 H8 106.2 . . ?
C14 C9 C10 117.2(10) . . ?
C14 C9 C8 123.8(9) . . ?
C10 C9 C8 119.0(9) . . ?
C11 C10 C9 121.4(9) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 121.2(11) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 118.4(11) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 119.6(9) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C9 121.9(10) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 122.5(10) . . ?
N2 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C16 C17 C18 118.9(12) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C19 117.7(10) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C20 C19 C18 121.2(10) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 N2 119.3(10) . . ?
C19 C20 C21 127.8(9) . . ?
N2 C20 C21 112.9(8) . . ?
C22 C21 C26 120.2(11) . . ?
C22 C21 C20 123.9(10) . . ?
C26 C21 C20 115.9(8) . . ?
C23 C22 F1 116.8(8) . . ?
C23 C22 C21 122.1(11) . . ?
F1 C22 C21 121.1(11) . . ?
C22 C23 C24 116.7(8) . . ?
C22 C23 H23 121.6 . . ?
C24 C23 H23 121.6 . . ?
F2 C24 C23 116.6(9) . . ?
F2 C24 C25 119.8(11) . . ?
C23 C24 C25 123.6(11) . . ?
C26 C25 C24 119.0(10) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C21 118.3(8) . . ?
C25 C26 Ir1 127.1(8) . . ?
C21 C26 Ir1 114.6(8) . . ?
N3 C27 C28 120.4(11) . . ?
N3 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 120.6(11) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.3(12) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C31 C30 C29 119.4(10) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
N3 C31 C30 118.9(9) . . ?
N3 C31 C32 111.9(9) . . ?
C30 C31 C32 129.1(9) . . ?
C33 C32 C37 116.8(10) . . ?
C33 C32 C31 125.4(10) . . ?
C37 C32 C31 117.6(9) . . ?
F3 C33 C32 120.0(10) . . ?
F3 C33 C34 116.3(10) . . ?
C32 C33 C34 123.6(10) . . ?
C35 C34 C33 116.5(10) . . ?
C35 C34 H34 121.7 . . ?
C33 C34 H34 121.7 . . ?
F4 C35 C34 117.7(10) . . ?
F4 C35 C36 119.7(10) . . ?
C34 C35 C36 122.5(10) . . ?
C37 C36 C35 120.4(10) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C32 119.9(9) . . ?
C36 C37 Ir1 127.8(8) . . ?
C32 C37 Ir1 112.2(7) . . ?
O2 C38 C39 120.1(7) . . ?
O2 C38 C43 125.2(8) . . ?
C39 C38 C43 114.7(9) . . ?
C40 C39 C38 124.5(8) . . ?
C40 C39 H39 117.8 . . ?
C38 C39 H39 117.8 . . ?
C39 C40 C41 118.6(8) . . ?
C39 C40 H40 120.7 . . ?
C41 C40 H40 120.7 . . ?
C42 C41 C40 120.1(9) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 121.4(8) . . ?
C41 C42 H42 119.3 . . ?
C43 C42 H42 119.3 . . ?
C42 C43 C44 114.4(7) . . ?
C42 C43 C38 120.7(8) . . ?
C44 C43 C38 124.3(8) . . ?
N4 C44 C43 128.2(8) . . ?
N4 C44 H44 115.9 . . ?
C43 C44 H44 115.9 . . ?
N4 C45 C46 111.1(7) . . ?
N4 C45 C52 113.9(7) . . ?
C46 C45 C52 111.1(7) . . ?
N4 C45 H45 106.7 . . ?
C46 C45 H45 106.7 . . ?
C52 C45 H45 106.7 . . ?
C47 C46 C51 119.5(8) . . ?
C47 C46 C45 121.3(8) . . ?
C51 C46 C45 119.1(8) . . ?
C48 C47 C46 120.3(10) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C47 C48 C49 119.5(12) . . ?
C47 C48 H48 120.2 . . ?
C49 C48 H48 120.2 . . ?
C50 C49 C48 122.2(10) . . ?
C50 C49 H49 118.9 . . ?
C48 C49 H49 118.9 . . ?
C49 C50 C51 118.5(9) . . ?
C49 C50 H50 120.8 . . ?
C51 C50 H50 120.8 . . ?
C46 C51 C50 119.8(9) . . ?
C46 C51 H51 120.1 . . ?
C50 C51 H51 120.1 . . ?
C45 C52 H52A 109.5 . . ?
C45 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C45 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
N5 C53 C54 123.2(10) . . ?
N5 C53 H53 118.4 . . ?
C54 C53 H53 118.4 . . ?
C55 C54 C53 119.3(10) . . ?
C55 C54 H54 120.4 . . ?
C53 C54 H54 120.4 . . ?
C54 C55 C56 118.4(10) . . ?
C54 C55 H55 120.8 . . ?
C56 C55 H55 120.8 . . ?
C55 C56 C57 120.8(10) . . ?
C55 C56 H56 119.6 . . ?
C57 C56 H56 119.6 . . ?
N5 C57 C56 121.2(9) . . ?
N5 C57 C58 111.4(8) . . ?
C56 C57 C58 127.4(8) . . ?
C59 C58 C63 118.5(9) . . ?
C59 C58 C57 125.0(9) . . ?
C63 C58 C57 116.6(8) . . ?
F5 C59 C60 116.0(8) . . ?
F5 C59 C58 120.2(9) . . ?
C60 C59 C58 123.9(9) . . ?
C59 C60 C61 115.8(8) . . ?
C59 C60 H60 122.1 . . ?
C61 C60 H60 122.1 . . ?
F6 C61 C62 120.0(10) . . ?
F6 C61 C60 116.8(8) . . ?
C62 C61 C60 123.1(10) . . ?
C61 C62 C63 119.1(9) . . ?
C61 C62 H62 120.4 . . ?
C63 C62 H62 120.4 . . ?
C58 C63 C62 119.5(8) . . ?
C58 C63 Ir2 113.8(7) . . ?
C62 C63 Ir2 126.4(7) . . ?
N6 C64 C65 122.8(10) . . ?
N6 C64 H64 118.6 . . ?
C65 C64 H64 118.6 . . ?
C64 C65 C66 119.6(10) . . ?
C64 C65 H65 120.2 . . ?
C66 C65 H65 120.2 . . ?
C65 C66 C67 118.3(10) . . ?
C65 C66 H66 120.8 . . ?
C67 C66 H66 120.8 . . ?
C66 C67 C68 121.1(8) . . ?
C66 C67 H67 119.5 . . ?
C68 C67 H67 119.5 . . ?
N6 C68 C67 118.5(9) . . ?
N6 C68 C69 113.6(9) . . ?
C67 C68 C69 127.9(8) . . ?
C70 C69 C68 127.2(9) . . ?
C70 C69 C74 118.1(9) . . ?
C68 C69 C74 114.7(8) . . ?
C71 C70 F7 118.5(9) . . ?
C71 C70 C69 123.6(10) . . ?
F7 C70 C69 117.8(9) . . ?
C70 C71 C72 118.0(9) . . ?
C70 C71 H71 121.0 . . ?
C72 C71 H71 121.0 . . ?
F8 C72 C71 118.6(9) . . ?
F8 C72 C73 120.5(11) . . ?
C71 C72 C73 120.9(10) . . ?
C74 C73 C72 123.3(11) . . ?
C74 C73 H73 118.4 . . ?
C72 C73 H73 118.4 . . ?
C73 C74 C69 116.1(9) . . ?
C73 C74 Ir2 130.0(8) . . ?
C69 C74 Ir2 113.4(7) . . ?
C37 Ir1 C26 89.0(3) . . ?
C37 Ir1 N3 81.3(4) . . ?
C26 Ir1 N3 94.1(4) . . ?
C37 Ir1 N2 95.4(4) . . ?
C26 Ir1 N2 81.2(4) . . ?
N3 Ir1 N2 174.3(3) . . ?
C37 Ir1 O1 174.6(4) . . ?
C26 Ir1 O1 88.0(3) . . ?
N3 Ir1 O1 94.3(3) . . ?
N2 Ir1 O1 88.6(3) . . ?
C37 Ir1 N1 95.0(3) . . ?
C26 Ir1 N1 174.7(3) . . ?
N3 Ir1 N1 90.0(3) . . ?
N2 Ir1 N1 94.9(3) . . ?
O1 Ir1 N1 88.3(3) . . ?
C74 Ir2 C63 87.6(4) . . ?
C74 Ir2 N5 93.5(4) . . ?
C63 Ir2 N5 79.8(4) . . ?
C74 Ir2 N6 81.7(4) . . ?
C63 Ir2 N6 97.6(4) . . ?
N5 Ir2 N6 174.6(3) . . ?
C74 Ir2 O2 172.6(3) . . ?
C63 Ir2 O2 86.3(3) . . ?
N5 Ir2 O2 89.5(3) . . ?
N6 Ir2 O2 95.0(3) . . ?
C74 Ir2 N4 97.9(3) . . ?
C63 Ir2 N4 173.9(4) . . ?
N5 Ir2 N4 97.2(3) . . ?
N6 Ir2 N4 85.8(3) . . ?
O2 Ir2 N4 88.4(2) . . ?
C7 N1 C8 116.1(7) . . ?
C7 N1 Ir1 123.3(6) . . ?
C8 N1 Ir1 120.5(5) . . ?
C16 N2 C20 120.1(9) . . ?
C16 N2 Ir1 124.5(7) . . ?
C20 N2 Ir1 115.4(7) . . ?
C27 N3 C31 120.3(10) . . ?
C27 N3 Ir1 122.9(8) . . ?
C31 N3 Ir1 116.8(6) . . ?
C44 N4 C45 116.9(7) . . ?
C44 N4 Ir2 122.9(5) . . ?
C45 N4 Ir2 120.1(6) . . ?
C53 N5 C57 116.8(8) . . ?
C53 N5 Ir2 125.0(6) . . ?
C57 N5 Ir2 117.9(6) . . ?
C64 N6 C68 119.7(9) . . ?
C64 N6 Ir2 124.3(7) . . ?
C68 N6 Ir2 115.7(6) . . ?
C1 O1 Ir1 128.0(6) . . ?
C38 O2 Ir2 126.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.550
_refine_diff_density_min         -1.705
_refine_diff_density_rms         0.219
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1033812'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H26 F4 Ir N3 O'
_chemical_formula_sum            'C37 H26 F4 Ir N3 O'
_chemical_formula_weight         796.81

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   9.8067(9)
_cell_length_b                   12.3224(11)
_cell_length_c                   27.064(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3270.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    4.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_process_details   sadabs

_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            19636
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6430
_reflns_number_gt                5902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0398P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(10)
_refine_ls_number_reflns         6430
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2858(6) 0.3827(5) 0.1757(2) 0.0392(14) Uani 1 1 d . . .
C2 C 0.2276(8) 0.2807(5) 0.1760(3) 0.0490(18) Uani 1 1 d . . .
H2 H 0.2323 0.2400 0.1472 0.059 Uiso 1 1 calc R . .
C3 C 0.1629(8) 0.2348(6) 0.2163(3) 0.0561(19) Uani 1 1 d . . .
H3 H 0.1290 0.1644 0.2150 0.067 Uiso 1 1 calc R . .
C4 C 0.1497(8) 0.2975(6) 0.2593(3) 0.0595(19) Uani 1 1 d . . .
H4 H 0.1056 0.2698 0.2870 0.071 Uiso 1 1 calc R . .
C5 C 0.2023(7) 0.3988(6) 0.2598(3) 0.0494(17) Uani 1 1 d . . .
H5 H 0.1933 0.4397 0.2885 0.059 Uiso 1 1 calc R . .
C6 C 0.2696(6) 0.4457(6) 0.2194(2) 0.0400(13) Uani 1 1 d . . .
C7 C 0.3209(6) 0.5533(6) 0.2263(2) 0.0410(14) Uani 1 1 d . . .
H7 H 0.3023 0.5835 0.2571 0.049 Uiso 1 1 calc R . .
C8 C 0.4316(6) 0.7232(5) 0.2152(2) 0.0394(14) Uani 1 1 d . . .
H8 H 0.5260 0.7334 0.2042 0.047 Uiso 1 1 calc R . .
C9 C 0.3482(6) 0.8121(5) 0.1912(2) 0.0381(13) Uani 1 1 d . . .
C10 C 0.4140(8) 0.9102(5) 0.1798(2) 0.0472(17) Uani 1 1 d . . .
H10 H 0.5060 0.9191 0.1870 0.057 Uiso 1 1 calc R . .
C11 C 0.3406(10) 0.9946(6) 0.1575(3) 0.059(2) Uani 1 1 d . . .
H11 H 0.3841 1.0588 0.1486 0.071 Uiso 1 1 calc R . .
C12 C 0.2038(10) 0.9814(6) 0.1488(3) 0.058(2) Uani 1 1 d . . .
H12 H 0.1546 1.0377 0.1344 0.070 Uiso 1 1 calc R . .
C13 C 0.1382(8) 0.8870(6) 0.1609(2) 0.0523(18) Uani 1 1 d . . .
H13 H 0.0454 0.8800 0.1545 0.063 Uiso 1 1 calc R . .
C14 C 0.2092(7) 0.8010(6) 0.1826(2) 0.0443(16) Uani 1 1 d . . .
H14 H 0.1641 0.7373 0.1911 0.053 Uiso 1 1 calc R . .
C15 C 0.4313(8) 0.7373(6) 0.2716(2) 0.0525(18) Uani 1 1 d . . .
H15A H 0.4681 0.8071 0.2799 0.079 Uiso 1 1 calc R . .
H15B H 0.4862 0.6816 0.2864 0.079 Uiso 1 1 calc R . .
H15C H 0.3396 0.7319 0.2837 0.079 Uiso 1 1 calc R . .
C16 C 0.1591(7) 0.5871(6) 0.0917(2) 0.0488(17) Uani 1 1 d . . .
H16 H 0.1483 0.5196 0.1066 0.059 Uiso 1 1 calc R . .
C17 C 0.0472(9) 0.6352(7) 0.0709(3) 0.062(2) Uani 1 1 d . . .
H17 H -0.0384 0.6028 0.0723 0.074 Uiso 1 1 calc R . .
C18 C 0.0665(8) 0.7344(7) 0.0476(3) 0.061(2) Uani 1 1 d . . .
H18 H -0.0070 0.7697 0.0329 0.074 Uiso 1 1 calc R . .
C19 C 0.1939(7) 0.7804(6) 0.0461(2) 0.0487(18) Uani 1 1 d . . .
H19 H 0.2070 0.8452 0.0291 0.058 Uiso 1 1 calc R . .
C20 C 0.3036(7) 0.7316(5) 0.0697(2) 0.0406(15) Uani 1 1 d . . .
C21 C 0.4439(7) 0.7720(5) 0.0754(2) 0.0389(13) Uani 1 1 d . . .
C22 C 0.4881(8) 0.8708(6) 0.0592(3) 0.0517(19) Uani 1 1 d . . .
C23 C 0.6181(8) 0.9084(6) 0.0673(3) 0.0541(19) Uani 1 1 d . . .
H23 H 0.6471 0.9754 0.0554 0.065 Uiso 1 1 calc R . .
C24 C 0.7018(8) 0.8423(6) 0.0936(3) 0.0529(18) Uani 1 1 d . . .
C25 C 0.6642(7) 0.7407(6) 0.1108(3) 0.0503(18) Uani 1 1 d . . .
H25 H 0.7260 0.6974 0.1279 0.060 Uiso 1 1 calc R . .
C26 C 0.5313(6) 0.7050(5) 0.1020(2) 0.0377(13) Uani 1 1 d . . .
C27 C 0.6801(7) 0.5134(6) 0.1947(3) 0.0447(16) Uani 1 1 d . . .
H27 H 0.6269 0.5501 0.2177 0.054 Uiso 1 1 calc R . .
C28 C 0.8082(7) 0.4735(6) 0.2088(3) 0.0505(18) Uani 1 1 d . . .
H28 H 0.8391 0.4829 0.2410 0.061 Uiso 1 1 calc R . .
C29 C 0.8863(7) 0.4212(7) 0.1753(3) 0.062(2) Uani 1 1 d . . .
H29 H 0.9717 0.3947 0.1841 0.075 Uiso 1 1 calc R . .
C30 C 0.8378(7) 0.4076(6) 0.1275(3) 0.063(2) Uani 1 1 d . . .
H30 H 0.8910 0.3718 0.1042 0.076 Uiso 1 1 calc R . .
C31 C 0.7106(7) 0.4468(6) 0.1144(2) 0.0466(16) Uani 1 1 d . . .
C32 C 0.6467(7) 0.4393(7) 0.0653(2) 0.0499(15) Uani 1 1 d . . .
C33 C 0.6951(9) 0.3826(8) 0.0254(3) 0.068(2) Uani 1 1 d . . .
C34 C 0.6300(11) 0.3756(8) -0.0194(3) 0.078(3) Uani 1 1 d . . .
H34 H 0.6663 0.3376 -0.0460 0.093 Uiso 1 1 calc R . .
C35 C 0.5062(9) 0.4294(8) -0.0220(3) 0.064(2) Uani 1 1 d . . .
C36 C 0.4504(8) 0.4876(5) 0.0156(2) 0.0491(16) Uani 1 1 d . . .
H36 H 0.3666 0.5217 0.0113 0.059 Uiso 1 1 calc R . .
C37 C 0.5181(7) 0.4965(5) 0.0605(2) 0.0417(15) Uani 1 1 d . . .
F1 F 0.4033(5) 0.9380(4) 0.03365(17) 0.0745(13) Uani 1 1 d . . .
F2 F 0.8306(5) 0.8773(4) 0.1042(2) 0.0845(16) Uani 1 1 d . . .
F3 F 0.4345(6) 0.4187(5) -0.06568(15) 0.0902(17) Uani 1 1 d . . .
F4 F 0.8186(6) 0.3321(6) 0.0287(2) 0.113(2) Uani 1 1 d . . .
Ir1 Ir 0.45218(2) 0.563226(19) 0.123618(8) 0.03447(7) Uani 1 1 d . . .
N1 N 0.3881(5) 0.6146(4) 0.19723(17) 0.0340(11) Uani 1 1 d . . .
N2 N 0.2845(5) 0.6326(4) 0.09170(18) 0.0378(12) Uani 1 1 d . . .
N3 N 0.6330(6) 0.4998(4) 0.14861(18) 0.0369(11) Uani 1 1 d . . .
O1 O 0.3518(5) 0.4128(3) 0.13701(15) 0.0450(11) 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
C1 O1 1.285(7) . ?
C1 C2 1.380(10) . ?
C1 C6 1.424(9) . ?
C2 C3 1.383(10) . ?
C3 C4 1.402(11) . ?
C4 C5 1.350(10) . ?
C5 C6 1.401(9) . ?
C6 C7 1.432(9) . ?
C7 N1 1.274(8) . ?
C8 N1 1.486(8) . ?
C8 C9 1.514(9) . ?
C8 C15 1.536(9) . ?
C9 C14 1.390(9) . ?
C9 C10 1.405(9) . ?
C10 C11 1.402(10) . ?
C11 C12 1.372(12) . ?
C12 C13 1.369(11) . ?
C13 C14 1.397(10) . ?
C16 N2 1.352(9) . ?
C16 C17 1.369(10) . ?
C17 C18 1.388(11) . ?
C18 C19 1.373(11) . ?
C19 C20 1.388(9) . ?
C20 N2 1.370(8) . ?
C20 C21 1.471(10) . ?
C21 C22 1.364(9) . ?
C21 C26 1.391(8) . ?
C22 F1 1.363(8) . ?
C22 C23 1.374(10) . ?
C23 C24 1.359(11) . ?
C24 F2 1.366(9) . ?
C24 C25 1.385(10) . ?
C25 C26 1.397(9) . ?
C26 Ir1 1.999(6) . ?
C27 N3 1.339(8) . ?
C27 C28 1.402(9) . ?
C28 C29 1.350(10) . ?
C29 C30 1.387(11) . ?
C30 C31 1.383(9) . ?
C31 N3 1.365(8) . ?
C31 C32 1.472(9) . ?
C32 C33 1.371(11) . ?
C32 C37 1.450(9) . ?
C33 F4 1.364(10) . ?
C33 C34 1.372(12) . ?
C34 C35 1.385(12) . ?
C35 C36 1.360(10) . ?
C35 F3 1.382(8) . ?
C36 C37 1.387(9) . ?
C37 Ir1 2.004(6) . ?
Ir1 N2 2.045(5) . ?
Ir1 N3 2.053(5) . ?
Ir1 O1 2.130(4) . ?
Ir1 N1 2.183(5) . ?

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 C1 C2 118.5(6) . . ?
O1 C1 C6 125.1(6) . . ?
C2 C1 C6 116.4(6) . . ?
C1 C2 C3 124.6(7) . . ?
C2 C3 C4 118.1(7) . . ?
C5 C4 C3 118.7(7) . . ?
C4 C5 C6 123.7(7) . . ?
C5 C6 C1 118.4(6) . . ?
C5 C6 C7 116.4(6) . . ?
C1 C6 C7 125.1(6) . . ?
N1 C7 C6 130.5(6) . . ?
N1 C8 C9 110.9(5) . . ?
N1 C8 C15 115.3(5) . . ?
C9 C8 C15 110.0(5) . . ?
C14 C9 C10 119.8(7) . . ?
C14 C9 C8 122.1(6) . . ?
C10 C9 C8 118.0(6) . . ?
C11 C10 C9 119.8(7) . . ?
C12 C11 C10 119.2(8) . . ?
C13 C12 C11 121.3(7) . . ?
C12 C13 C14 120.7(7) . . ?
C9 C14 C13 119.0(7) . . ?
N2 C16 C17 123.4(7) . . ?
C16 C17 C18 117.3(8) . . ?
C19 C18 C17 120.1(7) . . ?
C18 C19 C20 120.9(7) . . ?
N2 C20 C19 118.7(6) . . ?
N2 C20 C21 112.6(5) . . ?
C19 C20 C21 128.7(6) . . ?
C22 C21 C26 120.0(7) . . ?
C22 C21 C20 124.5(6) . . ?
C26 C21 C20 115.4(5) . . ?
C21 C22 F1 120.7(7) . . ?
C21 C22 C23 123.1(7) . . ?
F1 C22 C23 116.2(7) . . ?
C24 C23 C22 116.2(7) . . ?
C23 C24 F2 118.6(7) . . ?
C23 C24 C25 123.9(7) . . ?
F2 C24 C25 117.4(7) . . ?
C24 C25 C26 118.4(7) . . ?
C21 C26 C25 118.5(6) . . ?
C21 C26 Ir1 115.5(5) . . ?
C25 C26 Ir1 126.0(5) . . ?
N3 C27 C28 121.2(7) . . ?
C29 C28 C27 119.6(7) . . ?
C28 C29 C30 119.2(6) . . ?
C31 C30 C29 120.4(7) . . ?
N3 C31 C30 119.7(6) . . ?
N3 C31 C32 113.9(5) . . ?
C30 C31 C32 126.4(6) . . ?
C33 C32 C37 118.6(7) . . ?
C33 C32 C31 126.5(7) . . ?
C37 C32 C31 114.9(6) . . ?
F4 C33 C32 119.3(8) . . ?
F4 C33 C34 116.2(7) . . ?
C32 C33 C34 124.5(8) . . ?
C33 C34 C35 115.0(7) . . ?
C36 C35 F3 119.1(7) . . ?
C36 C35 C34 124.5(7) . . ?
F3 C35 C34 116.4(7) . . ?
C35 C36 C37 120.2(7) . . ?
C36 C37 C32 117.1(6) . . ?
C36 C37 Ir1 128.6(5) . . ?
C32 C37 Ir1 113.8(4) . . ?
C26 Ir1 C37 89.1(3) . . ?
C26 Ir1 N2 79.8(2) . . ?
C37 Ir1 N2 94.1(2) . . ?
C26 Ir1 N3 95.4(2) . . ?
C37 Ir1 N3 81.1(2) . . ?
N2 Ir1 N3 173.3(2) . . ?
C26 Ir1 O1 171.8(2) . . ?
C37 Ir1 O1 86.4(2) . . ?
N2 Ir1 O1 93.7(2) . . ?
N3 Ir1 O1 90.69(19) . . ?
C26 Ir1 N1 97.2(2) . . ?
C37 Ir1 N1 172.0(2) . . ?
N2 Ir1 N1 91.88(19) . . ?
N3 Ir1 N1 93.35(19) . . ?
O1 Ir1 N1 87.93(17) . . ?
C7 N1 C8 118.6(5) . . ?
C7 N1 Ir1 122.8(4) . . ?
C8 N1 Ir1 118.5(4) . . ?
C16 N2 C20 119.6(5) . . ?
C16 N2 Ir1 123.9(5) . . ?
C20 N2 Ir1 116.5(4) . . ?
C27 N3 C31 119.9(5) . . ?
C27 N3 Ir1 123.8(4) . . ?
C31 N3 Ir1 116.1(4) . . ?
C1 O1 Ir1 128.5(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.974
_refine_diff_density_min         -1.066
_refine_diff_density_rms         0.104
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1033813'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H26 F4 Ir N3 O'
_chemical_formula_sum            'C37 H26 F4 Ir N3 O'
_chemical_formula_weight         796.81

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   9.696(4)
_cell_length_b                   12.172(5)
_cell_length_c                   26.736(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3155(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    4.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4808
_exptl_absorpt_correction_T_max  0.6270
_exptl_absorpt_process_details   sadabs

_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            14815
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5969
_reflns_number_gt                5321
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0904P)²+17.9249P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         5969
_refine_ls_number_parameters     416
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.04823(4) 0.56485(4) 0.623949(16) 0.01687(14) Uani 1 1 d . . .
O1 O 0.1481(8) 0.4123(6) 0.6380(3) 0.0192(18) Uani 1 1 d . . .
F2 F 0.0654(9) 0.4131(7) 0.4332(3) 0.042(2) Uani 1 1 d . . .
F3 F 0.1015(8) 0.9416(7) 0.5311(3) 0.0375(18) Uani 1 1 d . . .
F1 F -0.3256(9) 0.3318(8) 0.5288(3) 0.042(2) Uani 1 1 d . . .
N2 N -0.1362(9) 0.5019(7) 0.6496(4) 0.0152(19) Uani 1 1 d . . .
C37 C -0.0300(10) 0.7075(10) 0.6015(4) 0.018(2) Uani 1 1 d . . .
C7 C 0.1794(10) 0.5580(11) 0.7283(4) 0.021(2) Uani 1 1 d . . .
H7 H 0.1985 0.5894 0.7593 0.025 Uiso 1 1 calc R . .
N3 N 0.2177(9) 0.6345(8) 0.5922(4) 0.018(2) Uani 1 1 d . . .
C6 C 0.2310(10) 0.4464(11) 0.7216(4) 0.018(2) Uani 1 1 d . . .
C27 C 0.3465(12) 0.5872(10) 0.5926(4) 0.021(3) Uani 1 1 d . . .
H27 H 0.3565 0.5181 0.6070 0.026 Uiso 1 1 calc R . .
C32 C 0.0611(12) 0.7750(9) 0.5740(4) 0.021(2) Uani 1 1 d . . .
C20 C -0.2133(11) 0.4506(10) 0.6156(4) 0.020(2) Uani 1 1 d . . .
C2 C 0.2763(13) 0.2800(12) 0.6781(5) 0.027(3) Uani 1 1 d . . .
H2 H 0.2734 0.2384 0.6489 0.032 Uiso 1 1 calc R . .
F4 F -0.3296(8) 0.8853(7) 0.6028(3) 0.038(2) Uani 1 1 d . . .
C19 C -0.3421(11) 0.4092(10) 0.6275(5) 0.027(3) Uani 1 1 d . . .
H19 H -0.3958 0.3742 0.6035 0.032 Uiso 1 1 calc R . .
C31 C 0.2013(12) 0.7335(11) 0.5686(5) 0.023(3) Uani 1 1 d . . .
C21 C -0.1488(12) 0.4412(12) 0.5663(5) 0.026(2) Uani 1 1 d . . .
N1 N 0.1123(9) 0.6188(9) 0.6984(4) 0.020(2) Uani 1 1 d . . .
C8 C 0.0657(12) 0.7269(10) 0.7160(4) 0.020(2) Uani 1 1 d . . .
H8 H -0.0302 0.7358 0.7051 0.024 Uiso 1 1 calc R . .
C28 C 0.4587(14) 0.6358(12) 0.5730(5) 0.032(3) Uani 1 1 d . . .
H28 H 0.5453 0.6034 0.5756 0.039 Uiso 1 1 calc R . .
C10 C 0.1492(11) 0.8170(10) 0.6911(4) 0.020(2) Uani 1 1 d . . .
C25 C 0.0483(14) 0.4881(10) 0.5148(5) 0.030(3) Uani 1 1 d . . .
H25 H 0.1321 0.5236 0.5098 0.036 Uiso 1 1 calc R . .
C13 C 0.2989(15) 0.9823(12) 0.6476(5) 0.030(3) Uani 1 1 d . . .
H13 H 0.3484 1.0382 0.6321 0.036 Uiso 1 1 calc R . .
C9 C 0.0687(12) 0.7443(10) 0.7730(5) 0.023(3) Uani 1 1 d . . .
H9A H 0.0193 0.6859 0.7892 0.035 Uiso 1 1 calc R . .
H9B H 0.0260 0.8133 0.7810 0.035 Uiso 1 1 calc R . .
H9C H 0.1625 0.7447 0.7844 0.035 Uiso 1 1 calc R . .
C24 C -0.0075(12) 0.4248(13) 0.4769(4) 0.027(3) Uani 1 1 d . . .
C11 C 0.2908(12) 0.8035(13) 0.6824(5) 0.027(3) Uani 1 1 d . . .
H11 H 0.3356 0.7386 0.6909 0.032 Uiso 1 1 calc R . .
C29 C 0.4413(14) 0.7376(11) 0.5483(5) 0.032(3) Uani 1 1 d . . .
H29 H 0.5165 0.7731 0.5340 0.038 Uiso 1 1 calc R . .
C18 C -0.3897(11) 0.4216(12) 0.6772(5) 0.027(3) Uani 1 1 d U . .
H18 H -0.4738 0.3919 0.6870 0.032 Uiso 1 1 calc R . .
C30 C 0.3137(12) 0.7827(11) 0.5457(5) 0.027(3) Uani 1 1 d . . .
H30 H 0.3013 0.8480 0.5282 0.032 Uiso 1 1 calc R . .
C12 C 0.3634(13) 0.8925(11) 0.6602(5) 0.026(3) Uani 1 1 d . . .
H12 H 0.4578 0.8865 0.6546 0.031 Uiso 1 1 calc R . .
C26 C -0.0202(11) 0.4992(11) 0.5609(4) 0.022(3) Uani 1 1 d . . .
C15 C 0.0854(13) 0.9124(11) 0.6781(5) 0.031(3) Uani 1 1 d . . .
H15 H -0.0087 0.9205 0.6838 0.037 Uiso 1 1 calc R . .
C3 C 0.3406(11) 0.2360(11) 0.7191(5) 0.026(3) Uani 1 1 d . . .
H3 H 0.3751 0.1647 0.7180 0.032 Uiso 1 1 calc R . .
C14 C 0.1591(13) 0.9978(11) 0.6565(5) 0.027(3) Uani 1 1 d . . .
H14 H 0.1161 1.0636 0.6482 0.032 Uiso 1 1 calc R . .
C1 C 0.2150(11) 0.3834(11) 0.6776(5) 0.022(3) Uani 1 1 d . . .
C35 C -0.2023(13) 0.8463(10) 0.5927(5) 0.025(3) Uani 1 1 d . . .
C4 C 0.3540(13) 0.2989(10) 0.7623(5) 0.027(3) Uani 1 1 d . . .
H4 H 0.4006 0.2718 0.7901 0.033 Uiso 1 1 calc R . .
C33 C 0.0158(13) 0.8712(12) 0.5567(5) 0.029(3) Uani 1 1 d . . .
C5 C 0.2989(12) 0.3979(12) 0.7628(5) 0.030(3) Uani 1 1 d . . .
H5 H 0.3050 0.4385 0.7922 0.036 Uiso 1 1 calc R . .
C36 C -0.1646(12) 0.7440(11) 0.6098(5) 0.026(3) Uani 1 1 d . . .
H36 H -0.2277 0.6999 0.6266 0.031 Uiso 1 1 calc R . .
C16 C -0.1809(11) 0.5151(11) 0.6961(5) 0.022(3) Uani 1 1 d . . .
H16 H -0.1245 0.5499 0.7193 0.026 Uiso 1 1 calc R . .
C34 C -0.1154(12) 0.9119(12) 0.5654(5) 0.029(3) Uani 1 1 d . . .
H34 H -0.1431 0.9800 0.5533 0.035 Uiso 1 1 calc R . .
C22 C -0.2009(13) 0.3797(12) 0.5250(5) 0.029(3) Uani 1 1 d . . .
C17 C -0.3095(12) 0.4781(11) 0.7107(5) 0.025(3) Uani 1 1 d . . .
H17 H -0.3413 0.4914 0.7430 0.030 Uiso 1 1 calc R . .
C23 C -0.1324(15) 0.3718(13) 0.4798(6) 0.036(3) Uani 1 1 d . . .
H23 H -0.1688 0.3331 0.4528 0.043 Uiso 1 1 calc R . .


_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 C26 1.979(13) . ?
Ir1 C37 1.987(12) . ?
Ir1 N3 2.034(9) . ?
Ir1 N2 2.063(9) . ?
Ir1 O1 2.127(8) . ?
Ir1 N1 2.185(10) . ?
O1 C1 1.291(15) . ?
F2 C24 1.373(14) . ?
F3 C33 1.377(15) . ?
F1 C22 1.347(14) . ?
N2 C16 1.325(16) . ?
N2 C20 1.332(14) . ?
C37 C36 1.396(15) . ?
C37 C32 1.412(16) . ?
C7 N1 1.270(16) . ?
C7 C6 1.459(19) . ?
C7 H7 0.9300 . ?
N3 C31 1.369(17) . ?
N3 C27 1.375(16) . ?
C6 C1 1.413(17) . ?
C6 C5 1.414(17) . ?
C27 C28 1.345(18) . ?
C27 H27 0.9300 . ?
C32 C33 1.334(18) . ?
C32 C31 1.458(17) . ?
C20 C19 1.384(15) . ?
C20 C21 1.464(16) . ?
C2 C3 1.369(18) . ?
C2 C1 1.39(2) . ?
C2 H2 0.9300 . ?
F4 C35 1.350(15) . ?
C19 C18 1.416(18) . ?
C19 H19 0.9300 . ?
C31 C30 1.386(17) . ?
C21 C22 1.426(18) . ?
C21 C26 1.441(18) . ?
N1 C8 1.469(15) . ?
C8 C10 1.517(16) . ?
C8 C9 1.541(17) . ?
C8 H8 0.9800 . ?
C28 C29 1.41(2) . ?
C28 H28 0.9300 . ?
C10 C15 1.361(18) . ?
C10 C11 1.402(16) . ?
C25 C24 1.383(18) . ?
C25 C26 1.407(18) . ?
C25 H25 0.9300 . ?
C13 C12 1.304(19) . ?
C13 C14 1.389(18) . ?
C13 H13 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C24 C23 1.374(18) . ?
C11 C12 1.42(2) . ?
C11 H11 0.9300 . ?
C29 C30 1.35(2) . ?
C29 H29 0.9300 . ?
C18 C17 1.370(18) . ?
C18 H18 0.9300 . ?
C30 H30 0.9300 . ?
C12 H12 0.9300 . ?
C15 C14 1.39(2) . ?
C15 H15 0.9300 . ?
C3 C4 1.394(19) . ?
C3 H3 0.9300 . ?
C14 H14 0.9300 . ?
C35 C34 1.372(19) . ?
C35 C36 1.375(18) . ?
C4 C5 1.318(19) . ?
C4 H4 0.9300 . ?
C33 C34 1.384(17) . ?
C5 H5 0.9300 . ?
C36 H36 0.9300 . ?
C16 C17 1.382(15) . ?
C16 H16 0.9300 . ?
C34 H34 0.9300 . ?
C22 C23 1.38(2) . ?
C17 H17 0.9300 . ?
C23 H23 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
C26 Ir1 C37 88.1(5) . . ?
C26 Ir1 N3 94.8(4) . . ?
C37 Ir1 N3 79.5(4) . . ?
C26 Ir1 N2 81.0(4) . . ?
C37 Ir1 N2 95.4(4) . . ?
N3 Ir1 N2 173.6(4) . . ?
C26 Ir1 O1 87.2(4) . . ?
C37 Ir1 O1 171.6(4) . . ?
N3 Ir1 O1 94.0(4) . . ?
N2 Ir1 O1 90.7(3) . . ?
C26 Ir1 N1 172.6(5) . . ?
C37 Ir1 N1 97.0(4) . . ?
N3 Ir1 N1 91.4(4) . . ?
N2 Ir1 N1 93.1(4) . . ?
O1 Ir1 N1 88.4(3) . . ?
C1 O1 Ir1 127.7(8) . . ?
C16 N2 C20 120.8(9) . . ?
C16 N2 Ir1 123.4(7) . . ?
C20 N2 Ir1 115.7(7) . . ?
C36 C37 C32 118.8(11) . . ?
C36 C37 Ir1 125.9(9) . . ?
C32 C37 Ir1 115.3(8) . . ?
N1 C7 C6 129.8(11) . . ?
N1 C7 H7 115.1 . . ?
C6 C7 H7 115.1 . . ?
C31 N3 C27 118.5(9) . . ?
C31 N3 Ir1 117.7(7) . . ?
C27 N3 Ir1 123.8(8) . . ?
C1 C6 C5 118.3(13) . . ?
C1 C6 C7 124.8(11) . . ?
C5 C6 C7 116.9(11) . . ?
C28 C27 N3 123.2(11) . . ?
C28 C27 H27 118.4 . . ?
N3 C27 H27 118.4 . . ?
C33 C32 C37 119.1(12) . . ?
C33 C32 C31 125.2(12) . . ?
C37 C32 C31 115.7(11) . . ?
N2 C20 C19 121.4(11) . . ?
N2 C20 C21 114.3(10) . . ?
C19 C20 C21 124.3(11) . . ?
C3 C2 C1 123.8(13) . . ?
C3 C2 H2 118.1 . . ?
C1 C2 H2 118.1 . . ?
C20 C19 C18 118.1(11) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
N3 C31 C30 119.5(11) . . ?
N3 C31 C32 111.6(10) . . ?
C30 C31 C32 128.8(13) . . ?
C22 C21 C26 119.1(11) . . ?
C22 C21 C20 126.0(11) . . ?
C26 C21 C20 114.9(11) . . ?
C7 N1 C8 118.5(10) . . ?
C7 N1 Ir1 123.0(9) . . ?
C8 N1 Ir1 118.3(8) . . ?
N1 C8 C10 110.1(9) . . ?
N1 C8 C9 115.8(10) . . ?
C10 C8 C9 108.9(10) . . ?
N1 C8 H8 107.2 . . ?
C10 C8 H8 107.2 . . ?
C9 C8 H8 107.2 . . ?
C27 C28 C29 118.1(12) . . ?
C27 C28 H28 121.0 . . ?
C29 C28 H28 121.0 . . ?
C15 C10 C11 120.2(13) . . ?
C15 C10 C8 119.1(11) . . ?
C11 C10 C8 120.7(12) . . ?
C24 C25 C26 120.7(12) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C12 C13 C14 122.5(13) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F2 C24 C23 116.8(11) . . ?
F2 C24 C25 118.7(11) . . ?
C23 C24 C25 124.5(12) . . ?
C10 C11 C12 117.7(13) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C30 C29 C28 119.2(12) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C17 C18 C19 118.8(10) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C29 C30 C31 121.3(13) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C13 C12 C11 120.6(12) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C25 C26 C21 116.7(12) . . ?
C25 C26 Ir1 128.8(9) . . ?
C21 C26 Ir1 113.8(8) . . ?
C10 C15 C14 120.7(12) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C2 C3 C4 119.4(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C15 C14 C13 118.2(12) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
O1 C1 C2 118.0(11) . . ?
O1 C1 C6 126.1(12) . . ?
C2 C1 C6 115.9(12) . . ?
F4 C35 C34 117.6(11) . . ?
F4 C35 C36 119.7(12) . . ?
C34 C35 C36 122.7(12) . . ?
C5 C4 C3 118.2(13) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C32 C33 F3 121.4(12) . . ?
C32 C33 C34 123.9(13) . . ?
F3 C33 C34 114.5(12) . . ?
C4 C5 C6 124.2(14) . . ?
C4 C5 H5 117.9 . . ?
C6 C5 H5 117.9 . . ?
C35 C36 C37 119.0(12) . . ?
C35 C36 H36 120.5 . . ?
C37 C36 H36 120.5 . . ?
N2 C16 C17 121.4(12) . . ?
N2 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C35 C34 C33 116.5(13) . . ?
C35 C34 H34 121.8 . . ?
C33 C34 H34 121.8 . . ?
F1 C22 C23 117.8(11) . . ?
F1 C22 C21 119.2(12) . . ?
C23 C22 C21 122.9(12) . . ?
C18 C17 C16 119.4(12) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C24 C23 C22 116.0(12) . . ?
C24 C23 H23 122.0 . . ?
C22 C23 H23 122.0 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         5.175
_refine_diff_density_min         -1.851
_refine_diff_density_rms         0.281
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1033814'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H26 F4 Ir N3 O'
_chemical_formula_sum            'C37 H26 F4 Ir N3 O'
_chemical_formula_weight         796.81

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'
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   'P2(1)   '
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   10.1586(4)
_cell_length_b                   16.4188(7)
_cell_length_c                   18.9530(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.3820(10)
_cell_angle_gamma                90.00
_cell_volume                     3118.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    4.340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_T_max  0.594
_exptl_absorpt_process_details   sadabs

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18800
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.09
_diffrn_reflns_theta_max         26.00
_reflns_number_total             11235
_reflns_number_gt                10588
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0000P)²+0.0000P] 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       ?
_chemical_absolute_configuration rm
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(4)
_refine_ls_number_reflns         11235
_refine_ls_number_parameters     831
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0486
_refine_ls_wR_factor_gt          0.0450
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_restrained_S_all      0.890
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1909(4) 0.9271(3) 0.0293(2) 0.0380(9) Uani 1 1 d . . .
C2 C 0.2592(5) 0.9990(3) 0.0137(2) 0.0477(11) Uani 1 1 d . . .
H2 H 0.2188 1.0493 0.0175 0.057 Uiso 1 1 calc R . .
C3 C 0.3810(5) 0.9965(3) -0.0066(3) 0.0560(12) Uani 1 1 d . . .
H3 H 0.4230 1.0448 -0.0157 0.067 Uiso 1 1 calc R . .
C4 C 0.4443(5) 0.9222(3) -0.0141(3) 0.0613(13) Uani 1 1 d . . .
H4 H 0.5291 0.9206 -0.0267 0.074 Uiso 1 1 calc R . .
C5 C 0.3782(4) 0.8512(3) -0.0025(2) 0.0570(11) Uani 1 1 d . . .
H5 H 0.4175 0.8014 -0.0097 0.068 Uiso 1 1 calc R . .
C6 C 0.2530(3) 0.8525(3) 0.0199(2) 0.0399(8) Uani 1 1 d . . .
C7 C 0.1927(4) 0.7732(3) 0.0243(2) 0.0423(10) Uani 1 1 d . . .
H7 H 0.2362 0.7303 0.0058 0.051 Uiso 1 1 calc R . .
C8 C 0.0424(4) 0.6671(3) 0.0421(2) 0.0404(8) Uani 1 1 d . . .
H8 H -0.0550 0.6682 0.0380 0.048 Uiso 1 1 calc R . .
C9 C 0.0928(4) 0.6173(3) 0.1075(2) 0.0458(10) Uani 1 1 d . . .
C10 C 0.2273(5) 0.6100(3) 0.1345(3) 0.0691(15) Uani 1 1 d . . .
H10 H 0.2891 0.6374 0.1120 0.083 Uiso 1 1 calc R . .
C11 C 0.2725(7) 0.5625(4) 0.1947(4) 0.088(2) Uani 1 1 d . . .
H11 H 0.3632 0.5592 0.2123 0.105 Uiso 1 1 calc R . .
C12 C 0.1837(8) 0.5211(4) 0.2274(3) 0.087(2) Uani 1 1 d . . .
H12 H 0.2139 0.4890 0.2672 0.104 Uiso 1 1 calc R . .
C13 C 0.0520(7) 0.5263(4) 0.2025(3) 0.0796(16) Uani 1 1 d . . .
H13 H -0.0083 0.4974 0.2249 0.096 Uiso 1 1 calc R . .
C14 C 0.0053(5) 0.5747(3) 0.1430(3) 0.0612(12) Uani 1 1 d . . .
H14 H -0.0860 0.5786 0.1270 0.073 Uiso 1 1 calc R . .
C15 C 0.0722(5) 0.6253(3) -0.0253(3) 0.0614(13) Uani 1 1 d . . .
H15A H 0.1663 0.6152 -0.0207 0.092 Uiso 1 1 calc R . .
H15B H 0.0444 0.6598 -0.0659 0.092 Uiso 1 1 calc R . .
H15C H 0.0248 0.5746 -0.0317 0.092 Uiso 1 1 calc R . .
C16 C 0.2119(5) 0.8086(3) 0.2114(3) 0.0551(12) Uani 1 1 d . . .
H16 H 0.2342 0.7705 0.1791 0.066 Uiso 1 1 calc R . .
C17 C 0.2910(6) 0.8151(4) 0.2788(3) 0.0785(19) Uani 1 1 d . . .
H17 H 0.3661 0.7824 0.2910 0.094 Uiso 1 1 calc R . .
C18 C 0.2557(7) 0.8706(4) 0.3265(3) 0.0805(19) Uani 1 1 d . . .
H18 H 0.3062 0.8753 0.3718 0.097 Uiso 1 1 calc R . .
C19 C 0.1460(6) 0.9191(4) 0.3073(3) 0.0705(15) Uani 1 1 d . . .
H19 H 0.1213 0.9563 0.3398 0.085 Uiso 1 1 calc R . .
C20 C 0.0711(5) 0.9127(3) 0.2386(2) 0.0483(10) Uani 1 1 d . . .
C21 C -0.0462(4) 0.9605(3) 0.2104(2) 0.0464(10) Uani 1 1 d . . .
C22 C -0.0923(5) 1.0286(3) 0.2420(3) 0.0606(13) Uani 1 1 d . . .
C23 C -0.2047(5) 1.0712(3) 0.2131(3) 0.0633(14) Uani 1 1 d . . .
H23 H -0.2336 1.1166 0.2357 0.076 Uiso 1 1 calc R . .
C24 C -0.2720(5) 1.0428(3) 0.1491(3) 0.0608(13) Uani 1 1 d . . .
C25 C -0.2325(4) 0.9761(3) 0.1136(2) 0.0496(10) Uani 1 1 d . . .
H25 H -0.2821 0.9590 0.0705 0.060 Uiso 1 1 calc R . .
C26 C -0.1163(4) 0.9343(3) 0.1435(2) 0.0414(10) Uani 1 1 d . . .
C27 C -0.1662(5) 0.8608(3) -0.0527(2) 0.0513(12) Uani 1 1 d . . .
H27 H -0.1002 0.8990 -0.0564 0.062 Uiso 1 1 calc R . .
C28 C -0.2567(5) 0.8411(5) -0.1130(2) 0.0680(13) Uani 1 1 d . . .
H28 H -0.2528 0.8668 -0.1563 0.082 Uiso 1 1 calc R . .
C29 C -0.3516(5) 0.7837(4) -0.1083(3) 0.0673(15) Uani 1 1 d . . .
H29 H -0.4121 0.7690 -0.1486 0.081 Uiso 1 1 calc R . .
C30 C -0.3568(4) 0.7476(3) -0.0433(3) 0.0574(13) Uani 1 1 d . . .
H30 H -0.4198 0.7074 -0.0398 0.069 Uiso 1 1 calc R . .
C31 C -0.2676(4) 0.7712(3) 0.0179(2) 0.0440(10) Uani 1 1 d . . .
C32 C -0.2609(4) 0.7420(3) 0.0912(2) 0.0422(10) Uani 1 1 d . . .
C33 C -0.3583(4) 0.6958(3) 0.1172(3) 0.0544(12) Uani 1 1 d . . .
C34 C -0.3460(6) 0.6700(3) 0.1881(3) 0.0728(16) Uani 1 1 d . . .
H34 H -0.4121 0.6398 0.2047 0.087 Uiso 1 1 calc R . .
C35 C -0.2303(6) 0.6919(3) 0.2316(3) 0.0678(15) Uani 1 1 d . . .
C36 C -0.1331(5) 0.7381(3) 0.2111(2) 0.0545(12) Uani 1 1 d . . .
H36 H -0.0581 0.7519 0.2440 0.065 Uiso 1 1 calc R . .
C37 C -0.1460(4) 0.7656(3) 0.1391(2) 0.0411(10) Uani 1 1 d . . .
C38 C 0.6508(4) 0.2801(3) 0.2779(2) 0.0448(10) Uani 1 1 d . . .
C39 C 0.7247(5) 0.2976(3) 0.2227(3) 0.0556(12) Uani 1 1 d . . .
H39 H 0.7799 0.2576 0.2087 0.067 Uiso 1 1 calc R . .
C40 C 0.7173(6) 0.3722(4) 0.1890(3) 0.0676(16) Uani 1 1 d . . .
H40 H 0.7671 0.3814 0.1527 0.081 Uiso 1 1 calc R . .
C41 C 0.6383(7) 0.4324(4) 0.2079(3) 0.0794(17) Uani 1 1 d . . .
H41 H 0.6339 0.4827 0.1849 0.095 Uiso 1 1 calc R . .
C42 C 0.5651(6) 0.4180(3) 0.2611(3) 0.0672(15) Uani 1 1 d . . .
H42 H 0.5113 0.4594 0.2741 0.081 Uiso 1 1 calc R . .
C43 C 0.5684(4) 0.3430(3) 0.2970(2) 0.0472(9) Uani 1 1 d . . .
C44 C 0.4898(4) 0.3377(3) 0.3539(2) 0.0495(10) Uani 1 1 d . . .
H44 H 0.4486 0.3859 0.3640 0.059 Uiso 1 1 calc R . .
C45 C 0.3868(5) 0.2939(3) 0.4511(2) 0.0545(12) Uani 1 1 d . . .
H45 H 0.3694 0.2413 0.4722 0.065 Uiso 1 1 calc R . .
C46 C 0.2522(4) 0.3306(4) 0.4219(2) 0.0565(12) Uani 1 1 d . . .
C47 C 0.1526(6) 0.2771(4) 0.3896(3) 0.0715(15) Uani 1 1 d . . .
H47 H 0.1705 0.2216 0.3882 0.086 Uiso 1 1 calc R . .
C48 C 0.0272(6) 0.3062(6) 0.3597(4) 0.092(2) Uani 1 1 d . . .
H48 H -0.0369 0.2708 0.3363 0.110 Uiso 1 1 calc R . .
C49 C -0.0011(6) 0.3871(7) 0.3647(4) 0.097(2) Uani 1 1 d . . .
H49 H -0.0853 0.4067 0.3455 0.117 Uiso 1 1 calc R . .
C50 C 0.0935(7) 0.4390(5) 0.3977(4) 0.090(2) Uani 1 1 d . . .
H50 H 0.0730 0.4939 0.4014 0.108 Uiso 1 1 calc R . .
C51 C 0.2218(5) 0.4110(4) 0.4263(3) 0.0691(15) Uani 1 1 d . . .
H51 H 0.2860 0.4474 0.4482 0.083 Uiso 1 1 calc R . .
C52 C 0.4705(5) 0.3431(5) 0.5097(3) 0.0788(17) Uani 1 1 d . . .
H52A H 0.4964 0.3935 0.4903 0.118 Uiso 1 1 calc R . .
H52B H 0.5488 0.3126 0.5290 0.118 Uiso 1 1 calc R . .
H52C H 0.4193 0.3542 0.5470 0.118 Uiso 1 1 calc R . .
C53 C 0.3044(5) 0.1706(4) 0.2674(2) 0.0582(13) Uani 1 1 d . . .
H53 H 0.2933 0.2211 0.2879 0.070 Uiso 1 1 calc R . .
C54 C 0.2104(6) 0.1444(4) 0.2110(3) 0.0702(17) Uani 1 1 d . . .
H54 H 0.1358 0.1761 0.1945 0.084 Uiso 1 1 calc R . .
C55 C 0.2284(7) 0.0718(5) 0.1799(3) 0.084(2) Uani 1 1 d . . .
H55 H 0.1655 0.0533 0.1421 0.101 Uiso 1 1 calc R . .
C56 C 0.3392(7) 0.0253(4) 0.2040(3) 0.0767(17) Uani 1 1 d . . .
H56 H 0.3529 -0.0235 0.1814 0.092 Uiso 1 1 calc R . .
C57 C 0.4318(5) 0.0517(3) 0.2628(2) 0.0573(13) Uani 1 1 d . . .
C58 C 0.5489(5) 0.0083(3) 0.2982(3) 0.0584(13) Uani 1 1 d . . .
C59 C 0.5950(7) -0.0670(4) 0.2782(3) 0.0769(18) Uani 1 1 d . . .
C60 C 0.7050(7) -0.1046(4) 0.3147(4) 0.088(2) Uani 1 1 d . . .
H60 H 0.7330 -0.1548 0.3000 0.106 Uiso 1 1 calc R . .
C61 C 0.7727(7) -0.0661(4) 0.3735(4) 0.0823(18) Uani 1 1 d . . .
C62 C 0.7334(6) 0.0084(4) 0.3954(3) 0.0673(14) Uani 1 1 d . . .
H62 H 0.7828 0.0332 0.4353 0.081 Uiso 1 1 calc R . .
C63 C 0.6217(5) 0.0471(3) 0.3592(2) 0.0522(11) Uani 1 1 d . . .
C64 C 0.8028(5) 0.2170(4) 0.4665(3) 0.0713(16) Uani 1 1 d . . .
H64 H 0.8185 0.2383 0.4232 0.086 Uiso 1 1 calc R . .
C65 C 0.8979(6) 0.2271(5) 0.5262(4) 0.091(2) Uani 1 1 d . . .
H65 H 0.9774 0.2542 0.5237 0.110 Uiso 1 1 calc R . .
C66 C 0.8723(7) 0.1965(5) 0.5887(4) 0.096(2) Uani 1 1 d . . .
H66 H 0.9351 0.2035 0.6298 0.115 Uiso 1 1 calc R . .
C67 C 0.7550(6) 0.1550(5) 0.5934(3) 0.0764(15) Uani 1 1 d . . .
H67 H 0.7400 0.1329 0.6365 0.092 Uiso 1 1 calc R . .
C68 C 0.6610(5) 0.1476(4) 0.5319(2) 0.0530(12) Uani 1 1 d . . .
C69 C 0.5294(5) 0.1087(3) 0.5243(2) 0.0521(11) Uani 1 1 d . . .
C70 C 0.4682(6) 0.0794(4) 0.5792(3) 0.0714(16) Uani 1 1 d . . .
C71 C 0.3439(7) 0.0445(5) 0.5690(3) 0.085(2) Uani 1 1 d . . .
H71 H 0.3053 0.0257 0.6072 0.102 Uiso 1 1 calc R . .
C72 C 0.2806(6) 0.0388(4) 0.5012(3) 0.0767(17) Uani 1 1 d . . .
C73 C 0.3328(5) 0.0670(3) 0.4438(3) 0.0585(13) Uani 1 1 d . . .
H73 H 0.2848 0.0615 0.3979 0.070 Uiso 1 1 calc R . .
C74 C 0.4587(5) 0.1042(3) 0.4539(2) 0.0465(10) Uani 1 1 d . . .
F1 F -0.0228(4) 1.0578(2) 0.30446(17) 0.0889(11) Uani 1 1 d . . .
F2 F -0.3824(4) 1.0835(2) 0.1183(2) 0.0917(11) Uani 1 1 d . . .
F3 F -0.4730(3) 0.6757(2) 0.07290(18) 0.0734(9) Uani 1 1 d . . .
F4 F -0.2153(4) 0.6658(3) 0.30090(18) 0.1077(14) Uani 1 1 d . . .
F5 F 0.5296(4) -0.1047(3) 0.2175(2) 0.1141(15) Uani 1 1 d . . .
F6 F 0.8831(5) -0.1028(3) 0.4080(3) 0.1213(16) Uani 1 1 d . . .
F7 F 0.5331(4) 0.0862(3) 0.64841(15) 0.1087(14) Uani 1 1 d . . .
F8 F 0.1573(4) 0.0037(3) 0.4893(2) 0.1219(19) Uani 1 1 d . . .
Ir1 Ir -0.026980(13) 0.842542(8) 0.098368(7) 0.03405(4) Uani 1 1 d . . .
Ir2 Ir 0.549336(16) 0.157083(10) 0.380024(8) 0.04165(5) Uani 1 1 d . . .
N1 N 0.0872(3) 0.7537(2) 0.05006(17) 0.0360(7) Uani 1 1 d . . .
N2 N 0.1040(3) 0.8564(2) 0.19209(17) 0.0422(9) Uani 1 1 d . . .
N3 N -0.1709(3) 0.8266(2) 0.01055(18) 0.0416(9) Uani 1 1 d . . .
N4 N 0.4684(3) 0.2765(2) 0.39257(17) 0.0447(8) Uani 1 1 d . . .
N5 N 0.4118(4) 0.1251(3) 0.29341(19) 0.0519(10) Uani 1 1 d . . .
N6 N 0.6881(4) 0.1774(2) 0.4685(2) 0.0505(11) Uani 1 1 d . . .
O1 O 0.0755(3) 0.93490(19) 0.05061(17) 0.0447(7) Uani 1 1 d . . .
O2 O 0.6659(3) 0.2090(2) 0.30802(16) 0.0525(8) 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
C1 O1 1.308(5) . ?
C1 C6 1.402(6) . ?
C1 C2 1.426(6) . ?
C2 C3 1.355(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.446(6) . ?
C7 N1 1.289(5) . ?
C7 H7 0.9300 . ?
C8 N1 1.494(5) . ?
C8 C9 1.504(6) . ?
C8 C15 1.522(6) . ?
C8 H8 0.9800 . ?
C9 C10 1.384(6) . ?
C9 C14 1.388(7) . ?
C10 C11 1.395(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.347(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N2 1.349(6) . ?
C16 C17 1.397(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.400(6) . ?
C19 H19 0.9300 . ?
C20 N2 1.356(6) . ?
C20 C21 1.455(7) . ?
C21 C22 1.384(7) . ?
C21 C26 1.416(6) . ?
C22 F1 1.362(6) . ?
C22 C23 1.375(8) . ?
C23 C24 1.374(7) . ?
C23 H23 0.9300 . ?
C24 F2 1.353(6) . ?
C24 C25 1.380(7) . ?
C25 C26 1.403(6) . ?
C25 H25 0.9300 . ?
C26 Ir1 2.019(4) . ?
C27 N3 1.331(6) . ?
C27 C28 1.384(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.361(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.376(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.405(6) . ?
C30 H30 0.9300 . ?
C31 N3 1.362(6) . ?
C31 C32 1.461(6) . ?
C32 C33 1.400(6) . ?
C32 C37 1.412(6) . ?
C33 F3 1.361(5) . ?
C33 C34 1.394(8) . ?
C34 C35 1.369(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.352(7) . ?
C35 F4 1.366(6) . ?
C36 C37 1.423(6) . ?
C36 H36 0.9300 . ?
C37 Ir1 1.989(4) . ?
C38 O2 1.298(6) . ?
C38 C39 1.413(7) . ?
C38 C43 1.413(6) . ?
C39 C40 1.377(7) . ?
C39 H39 0.9300 . ?
C40 C41 1.358(8) . ?
C40 H40 0.9300 . ?
C41 C42 1.369(8) . ?
C41 H41 0.9300 . ?
C42 C43 1.403(7) . ?
C42 H42 0.9300 . ?
C43 C44 1.444(6) . ?
C44 N4 1.284(6) . ?
C44 H44 0.9300 . ?
C45 C52 1.517(7) . ?
C45 C46 1.514(7) . ?
C45 N4 1.517(5) . ?
C45 H45 0.9800 . ?
C46 C51 1.362(8) . ?
C46 C47 1.403(8) . ?
C47 C48 1.392(9) . ?
C47 H47 0.9300 . ?
C48 C49 1.366(11) . ?
C48 H48 0.9300 . ?
C49 C50 1.358(11) . ?
C49 H49 0.9300 . ?
C50 C51 1.406(8) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 N5 1.347(7) . ?
C53 C54 1.381(7) . ?
C53 H53 0.9300 . ?
C54 C55 1.355(10) . ?
C54 H54 0.9300 . ?
C55 C56 1.375(9) . ?
C55 H55 0.9300 . ?
C56 C57 1.405(7) . ?
C56 H56 0.9300 . ?
C57 N5 1.367(6) . ?
C57 C58 1.454(8) . ?
C58 C59 1.395(8) . ?
C58 C63 1.419(7) . ?
C59 C60 1.362(10) . ?
C59 F5 1.378(7) . ?
C60 C61 1.365(10) . ?
C60 H60 0.9300 . ?
C61 F6 1.346(8) . ?
C61 C62 1.371(8) . ?
C62 C63 1.382(7) . ?
C62 H62 0.9300 . ?
C63 Ir2 2.012(5) . ?
C64 N6 1.339(7) . ?
C64 C65 1.373(8) . ?
C64 H64 0.9300 . ?
C65 C66 1.350(10) . ?
C65 H65 0.9300 . ?
C66 C67 1.388(9) . ?
C66 H66 0.9300 . ?
C67 C68 1.386(6) . ?
C67 H67 0.9300 . ?
C68 N6 1.367(6) . ?
C68 C69 1.468(7) . ?
C69 C70 1.382(7) . ?
C69 C74 1.410(6) . ?
C70 C71 1.371(8) . ?
C70 F7 1.373(5) . ?
C71 C72 1.344(8) . ?
C71 H71 0.9300 . ?
C72 F8 1.365(7) . ?
C72 C73 1.366(7) . ?
C73 C74 1.402(7) . ?
C73 H73 0.9300 . ?
C74 Ir2 1.996(4) . ?
Ir1 N3 2.045(3) . ?
Ir1 N2 2.051(3) . ?
Ir1 O1 2.123(3) . ?
Ir1 N1 2.158(3) . ?
Ir2 N6 2.034(4) . ?
Ir2 N5 2.043(4) . ?
Ir2 O2 2.126(3) . ?
Ir2 N4 2.154(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 124.7(4) . . ?
O1 C1 C2 118.3(4) . . ?
C6 C1 C2 117.0(4) . . ?
C3 C2 C1 122.1(4) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.6(5) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 119.9(4) . . ?
C1 C6 C7 125.1(3) . . ?
C5 C6 C7 114.6(4) . . ?
N1 C7 C6 129.1(4) . . ?
N1 C7 H7 115.4 . . ?
C6 C7 H7 115.4 . . ?
N1 C8 C9 112.1(3) . . ?
N1 C8 C15 114.5(4) . . ?
C9 C8 C15 111.0(4) . . ?
N1 C8 H8 106.2 . . ?
C9 C8 H8 106.2 . . ?
C15 C8 H8 106.2 . . ?
C10 C9 C14 116.6(4) . . ?
C10 C9 C8 122.3(4) . . ?
C14 C9 C8 121.0(4) . . ?
C9 C10 C11 121.6(5) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 119.9(6) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.2(6) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.4(6) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 121.2(5) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 121.7(5) . . ?
N2 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 118.6(6) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C19 C18 C17 120.0(5) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 119.9(5) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
N2 C20 C19 120.1(5) . . ?
N2 C20 C21 113.8(4) . . ?
C19 C20 C21 126.1(5) . . ?
C22 C21 C26 118.5(4) . . ?
C22 C21 C20 126.3(4) . . ?
C26 C21 C20 115.2(4) . . ?
F1 C22 C23 116.5(5) . . ?
F1 C22 C21 119.7(5) . . ?
C23 C22 C21 123.8(5) . . ?
C24 C23 C22 116.2(5) . . ?
C24 C23 H23 121.9 . . ?
C22 C23 H23 121.9 . . ?
F2 C24 C23 118.1(5) . . ?
F2 C24 C25 118.0(5) . . ?
C23 C24 C25 123.9(5) . . ?
C24 C25 C26 118.9(5) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C21 118.7(4) . . ?
C25 C26 Ir1 126.8(3) . . ?
C21 C26 Ir1 114.3(3) . . ?
N3 C27 C28 121.9(5) . . ?
N3 C27 H27 119.0 . . ?
C28 C27 H27 119.0 . . ?
C29 C28 C27 119.3(5) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C28 C29 C30 119.2(5) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C29 C30 C31 120.5(5) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
N3 C31 C30 118.6(4) . . ?
N3 C31 C32 113.2(4) . . ?
C30 C31 C32 128.2(4) . . ?
C33 C32 C37 118.7(4) . . ?
C33 C32 C31 126.0(4) . . ?
C37 C32 C31 115.3(4) . . ?
F3 C33 C32 119.8(5) . . ?
F3 C33 C34 117.1(4) . . ?
C32 C33 C34 123.2(5) . . ?
C35 C34 C33 115.7(5) . . ?
C35 C34 H34 122.1 . . ?
C33 C34 H34 122.1 . . ?
C36 C35 C34 124.7(5) . . ?
C36 C35 F4 118.7(5) . . ?
C34 C35 F4 116.5(5) . . ?
C35 C36 C37 119.8(5) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C32 C37 C36 117.9(4) . . ?
C32 C37 Ir1 114.5(3) . . ?
C36 C37 Ir1 127.4(3) . . ?
O2 C38 C39 118.0(4) . . ?
O2 C38 C43 125.3(4) . . ?
C39 C38 C43 116.7(4) . . ?
C40 C39 C38 121.9(5) . . ?
C40 C39 H39 119.0 . . ?
C38 C39 H39 119.0 . . ?
C41 C40 C39 121.0(5) . . ?
C41 C40 H40 119.5 . . ?
C39 C40 H40 119.5 . . ?
C40 C41 C42 118.9(5) . . ?
C40 C41 H41 120.5 . . ?
C42 C41 H41 120.5 . . ?
C41 C42 C43 122.4(5) . . ?
C41 C42 H42 118.8 . . ?
C43 C42 H42 118.8 . . ?
C42 C43 C38 119.0(4) . . ?
C42 C43 C44 116.2(5) . . ?
C38 C43 C44 124.7(5) . . ?
N4 C44 C43 129.8(5) . . ?
N4 C44 H44 115.1 . . ?
C43 C44 H44 115.1 . . ?
C52 C45 C46 115.0(5) . . ?
C52 C45 N4 109.2(4) . . ?
C46 C45 N4 112.1(4) . . ?
C52 C45 H45 106.7 . . ?
C46 C45 H45 106.7 . . ?
N4 C45 H45 106.7 . . ?
C51 C46 C47 118.7(5) . . ?
C51 C46 C45 124.3(5) . . ?
C47 C46 C45 117.0(5) . . ?
C46 C47 C48 120.6(7) . . ?
C46 C47 H47 119.7 . . ?
C48 C47 H47 119.7 . . ?
C49 C48 C47 119.7(7) . . ?
C49 C48 H48 120.1 . . ?
C47 C48 H48 120.1 . . ?
C50 C49 C48 120.1(7) . . ?
C50 C49 H49 120.0 . . ?
C48 C49 H49 120.0 . . ?
C49 C50 C51 121.0(7) . . ?
C49 C50 H50 119.5 . . ?
C51 C50 H50 119.5 . . ?
C46 C51 C50 119.9(6) . . ?
C46 C51 H51 120.0 . . ?
C50 C51 H51 120.0 . . ?
C45 C52 H52A 109.5 . . ?
C45 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C45 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
N5 C53 C54 121.8(6) . . ?
N5 C53 H53 119.1 . . ?
C54 C53 H53 119.1 . . ?
C55 C54 C53 119.0(6) . . ?
C55 C54 H54 120.5 . . ?
C53 C54 H54 120.5 . . ?
C54 C55 C56 120.3(5) . . ?
C54 C55 H55 119.8 . . ?
C56 C55 H55 119.8 . . ?
C55 C56 C57 119.9(6) . . ?
C55 C56 H56 120.1 . . ?
C57 C56 H56 120.1 . . ?
N5 C57 C56 118.8(6) . . ?
N5 C57 C58 113.8(4) . . ?
C56 C57 C58 127.3(5) . . ?
C59 C58 C63 117.7(5) . . ?
C59 C58 C57 126.5(5) . . ?
C63 C58 C57 115.7(4) . . ?
C60 C59 F5 117.6(6) . . ?
C60 C59 C58 123.2(6) . . ?
F5 C59 C58 119.1(6) . . ?
C61 C60 C59 117.8(6) . . ?
C61 C60 H60 121.1 . . ?
C59 C60 H60 121.1 . . ?
F6 C61 C60 117.3(6) . . ?
F6 C61 C62 120.8(7) . . ?
C60 C61 C62 121.8(7) . . ?
C61 C62 C63 121.1(6) . . ?
C61 C62 H62 119.5 . . ?
C63 C62 H62 119.5 . . ?
C62 C63 C58 118.3(5) . . ?
C62 C63 Ir2 127.8(4) . . ?
C58 C63 Ir2 113.9(4) . . ?
N6 C64 C65 122.4(6) . . ?
N6 C64 H64 118.8 . . ?
C65 C64 H64 118.8 . . ?
C66 C65 C64 117.8(6) . . ?
C66 C65 H65 121.1 . . ?
C64 C65 H65 121.1 . . ?
C65 C66 C67 122.0(6) . . ?
C65 C66 H66 119.0 . . ?
C67 C66 H66 119.0 . . ?
C68 C67 C66 118.1(6) . . ?
C68 C67 H67 121.0 . . ?
C66 C67 H67 121.0 . . ?
N6 C68 C67 119.8(5) . . ?
N6 C68 C69 112.4(4) . . ?
C67 C68 C69 127.8(5) . . ?
C70 C69 C74 118.1(4) . . ?
C70 C69 C68 126.3(4) . . ?
C74 C69 C68 115.5(4) . . ?
C71 C70 F7 117.1(5) . . ?
C71 C70 C69 123.8(5) . . ?
F7 C70 C69 119.1(5) . . ?
C72 C71 C70 116.7(5) . . ?
C72 C71 H71 121.6 . . ?
C70 C71 H71 121.6 . . ?
C71 C72 F8 118.1(5) . . ?
C71 C72 C73 123.4(5) . . ?
F8 C72 C73 118.5(5) . . ?
C72 C73 C74 120.2(5) . . ?
C72 C73 H73 119.9 . . ?
C74 C73 H73 119.9 . . ?
C73 C74 C69 117.7(4) . . ?
C73 C74 Ir2 127.5(3) . . ?
C69 C74 Ir2 114.8(3) . . ?
C37 Ir1 C26 88.03(16) . . ?
C37 Ir1 N3 80.53(16) . . ?
C26 Ir1 N3 97.44(16) . . ?
C37 Ir1 N2 94.82(16) . . ?
C26 Ir1 N2 79.80(17) . . ?
N3 Ir1 N2 174.72(14) . . ?
C37 Ir1 O1 171.86(15) . . ?
C26 Ir1 O1 86.16(16) . . ?
N3 Ir1 O1 94.57(13) . . ?
N2 Ir1 O1 89.76(13) . . ?
C37 Ir1 N1 97.97(16) . . ?
C26 Ir1 N1 173.52(16) . . ?
N3 Ir1 N1 86.03(13) . . ?
N2 Ir1 N1 97.17(13) . . ?
O1 Ir1 N1 88.10(10) . . ?
C74 Ir2 C63 88.38(19) . . ?
C74 Ir2 N6 80.21(17) . . ?
C63 Ir2 N6 94.74(18) . . ?
C74 Ir2 N5 96.83(17) . . ?
C63 Ir2 N5 80.57(19) . . ?
N6 Ir2 N5 174.57(17) . . ?
C74 Ir2 O2 173.71(16) . . ?
C63 Ir2 O2 88.55(15) . . ?
N6 Ir2 O2 94.57(14) . . ?
N5 Ir2 O2 88.08(14) . . ?
C74 Ir2 N4 95.20(17) . . ?
C63 Ir2 N4 175.11(16) . . ?
N6 Ir2 N4 89.15(14) . . ?
N5 Ir2 N4 95.68(15) . . ?
O2 Ir2 N4 88.19(13) . . ?
C7 N1 C8 117.2(3) . . ?
C7 N1 Ir1 122.1(3) . . ?
C8 N1 Ir1 120.7(2) . . ?
C16 N2 C20 119.7(4) . . ?
C16 N2 Ir1 123.7(3) . . ?
C20 N2 Ir1 116.4(3) . . ?
C27 N3 C31 120.4(4) . . ?
C27 N3 Ir1 123.5(3) . . ?
C31 N3 Ir1 115.8(3) . . ?
C44 N4 C45 115.8(4) . . ?
C44 N4 Ir2 123.1(3) . . ?
C45 N4 Ir2 121.1(3) . . ?
C53 N5 C57 120.0(4) . . ?
C53 N5 Ir2 124.0(3) . . ?
C57 N5 Ir2 116.0(4) . . ?
C64 N6 C68 119.9(4) . . ?
C64 N6 Ir2 123.1(4) . . ?
C68 N6 Ir2 117.0(3) . . ?
C1 O1 Ir1 126.0(3) . . ?
C38 O2 Ir2 127.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.057
