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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
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data_20170104zyx_xp_0m
_database_code_depnum_ccdc_archive 'CCDC 1535473'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-07-19 downloaded from the CCDC.
;
_audit_creation_date             2017-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C54 H31 F4 Ir N6 O2'
_chemical_formula_sum            'C54 H31 F4 Ir N6 O2'
_chemical_formula_weight         1064.05
_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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.928(10)
_cell_length_b                   18.643(6)
_cell_length_c                   22.998(8)
_cell_angle_alpha                90
_cell_angle_beta                 135.639(5)
_cell_angle_gamma                90
_cell_volume                     8972(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4554
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.372
_cell_measurement_theta_min      2.185
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.043
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4208
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            30648
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.761
_diffrn_reflns_theta_min         1.463
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6802
_reflns_number_total             10389
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         10389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      0.930
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0778
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C25(H25), C2(H2), C4(H4), C39(H39), C38(H38), C45(H45), C24(H24),
 C34(H34), C43(H43), C42(H42), C22(H22), C30(H30), C44(H44), C14(H14), C19(H19),
  C16(H16), C10(H10), C18(H18), C11(H11), C17(H17), C37(H37), C50(H50),
 C52(H52), C54(H54), C53(H53), C51(H51), C36(H36), C13(H13), C33(H33), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.21198(2) 0.44054(2) 0.30014(2) 0.03418(6) Uani 1 1 d . . . . .
N3 N 0.30768(16) 0.4504(2) 0.4103(2) 0.0387(9) Uani 1 1 d . . . . .
N1 N 0.11651(15) 0.4400(2) 0.1879(2) 0.0357(8) Uani 1 1 d . . . . .
O1 O 0.20550(14) 0.48829(17) 0.37893(18) 0.0447(8) Uani 1 1 d . . . . .
N6 N 0.17672(17) 0.2766(2) 0.2857(2) 0.0442(10) Uani 1 1 d . . . . .
O2 O 0.17333(15) 0.26523(17) 0.37792(19) 0.0474(8) Uani 1 1 d . . . . .
F1 F 0.31848(13) 0.34795(17) 0.19876(17) 0.0636(9) Uani 1 1 d . . . . .
C21 C 0.2287(2) 0.5388(2) 0.2852(3) 0.0378(11) Uani 1 1 d . . . . .
N5 N 0.19310(16) 0.3422(2) 0.3272(2) 0.0390(9) Uani 1 1 d . . . . .
F3 F 0.17674(13) 0.68706(16) 0.14781(16) 0.0655(8) Uani 1 1 d . . . . .
C27 C 0.3226(2) 0.5209(3) 0.4309(3) 0.0396(11) Uani 1 1 d . . . . .
C1 C 0.2175(2) 0.3960(2) 0.2270(2) 0.0338(10) Uani 1 1 d . . . . .
C5 C 0.1541(2) 0.3427(2) 0.0892(3) 0.0395(11) Uani 1 1 d . . . . .
H5 H 0.1147 0.3278 0.0383 0.047 Uiso 1 1 calc R . . . .
C26 C 0.2828(2) 0.5704(3) 0.3615(3) 0.0403(11) Uani 1 1 d . . . . .
C6 C 0.15814(19) 0.3732(2) 0.1486(2) 0.0331(10) Uani 1 1 d . . . . .
C25 C 0.3005(2) 0.6413(3) 0.3645(3) 0.0462(12) Uani 1 1 d . . . . .
H25 H 0.3365 0.6616 0.4150 0.055 Uiso 1 1 calc R . . . .
C23 C 0.2117(2) 0.6486(3) 0.2190(3) 0.0471(13) Uani 1 1 d . . . . .
C46 C 0.1975(2) 0.3844(3) 0.4340(3) 0.0442(12) Uani 1 1 d . . . . .
C2 C 0.2717(2) 0.3863(2) 0.2423(3) 0.0375(11) Uani 1 1 d . . . . .
H2 H 0.3118 0.3999 0.2930 0.045 Uiso 1 1 calc R . . . .
C7 C 0.1031(2) 0.3933(3) 0.1327(3) 0.0401(11) Uani 1 1 d . . . . .
C48 C 0.1661(2) 0.2331(3) 0.3181(3) 0.0438(12) Uani 1 1 d . . . . .
C4 C 0.2075(2) 0.3349(3) 0.1058(3) 0.0436(12) Uani 1 1 d . . . . .
H4 H 0.2052 0.3155 0.0665 0.052 Uiso 1 1 calc R . . . .
C3 C 0.2650(2) 0.3567(3) 0.1822(3) 0.0408(11) Uani 1 1 d . . . . .
C41 C 0.20413(19) 0.4588(3) 0.4288(3) 0.0407(12) Uani 1 1 d . . . . .
C28 C 0.3770(2) 0.5389(3) 0.5172(3) 0.0452(12) Uani 1 1 d . . . . .
N2 N -0.00988(19) 0.4118(3) 0.0381(2) 0.0595(13) Uani 1 1 d . . . . .
C40 C 0.3519(2) 0.3995(3) 0.4665(3) 0.0428(12) Uani 1 1 d . . . . .
C35 C 0.4100(2) 0.4219(3) 0.5462(3) 0.0486(13) Uani 1 1 d . . . . .
C49 C 0.1463(2) 0.1583(3) 0.2984(3) 0.0457(12) Uani 1 1 d . . . . .
C29 C 0.3839(2) 0.6109(3) 0.5506(3) 0.0492(13) Uani 1 1 d . . . . .
C15 C 0.0046(2) 0.4681(3) 0.0868(3) 0.0564(15) Uani 1 1 d . . . . .
C39 C 0.3418(2) 0.3271(3) 0.4453(3) 0.0460(12) Uani 1 1 d . . . . .
H39 H 0.3034 0.3117 0.3935 0.055 Uiso 1 1 calc R . . . .
C38 C 0.3896(2) 0.2785(3) 0.5025(3) 0.0585(15) Uani 1 1 d . . . . .
H38 H 0.3839 0.2303 0.4881 0.070 Uiso 1 1 calc R . . . .
N4 N 0.41972(19) 0.4905(2) 0.5719(2) 0.0534(11) Uani 1 1 d . . . . .
C9 C 0.0186(2) 0.3054(3) 0.0164(3) 0.0515(14) Uani 1 1 d . . . . .
C45 C 0.1953(2) 0.3594(3) 0.4893(3) 0.0564(14) Uani 1 1 d . . . . .
H45 H 0.1909 0.3105 0.4919 0.068 Uiso 1 1 calc R . . . .
C24 C 0.2639(2) 0.6805(3) 0.2920(3) 0.0489(12) Uani 1 1 d . . . . .
H24 H 0.2746 0.7276 0.2927 0.059 Uiso 1 1 calc R . . . .
C34 C 0.4433(3) 0.6441(3) 0.6064(3) 0.0725(18) Uani 1 1 d . . . . .
H34 H 0.4783 0.6221 0.6215 0.087 Uiso 1 1 calc R . . . .
C43 C 0.2070(2) 0.4775(3) 0.5363(3) 0.0581(15) Uani 1 1 d . . . . .
H43 H 0.2111 0.5088 0.5714 0.070 Uiso 1 1 calc R . . . .
C42 C 0.2082(2) 0.5034(3) 0.4823(3) 0.0515(13) Uani 1 1 d . . . . .
H42 H 0.2118 0.5527 0.4803 0.062 Uiso 1 1 calc R . . . .
C22 C 0.1927(2) 0.5796(3) 0.2126(3) 0.0416(12) Uani 1 1 d . . . . .
H22 H 0.1568 0.5603 0.1612 0.050 Uiso 1 1 calc R . . . .
C30 C 0.3340(3) 0.6416(3) 0.5324(3) 0.0681(17) Uani 1 1 d . . . . .
H30 H 0.2944 0.6190 0.4958 0.082 Uiso 1 1 calc R . . . .
C20 C 0.0677(2) 0.4801(3) 0.1664(3) 0.0440(12) Uani 1 1 d . . . . .
C47 C 0.1892(2) 0.3339(3) 0.3799(3) 0.0404(11) Uani 1 1 d . . . . .
C8 C 0.0373(2) 0.3741(3) 0.0614(3) 0.0483(13) Uani 1 1 d . . . . .
C44 C 0.1995(3) 0.4047(3) 0.5394(3) 0.0689(17) Uani 1 1 d . . . . .
H44 H 0.1974 0.3871 0.5752 0.083 Uiso 1 1 calc R . . . .
C14 C -0.0359(2) 0.3006(3) -0.0682(3) 0.0659(17) Uani 1 1 d . . . . .
H14 H -0.0574 0.3424 -0.0985 0.079 Uiso 1 1 calc R . . . .
C19 C 0.0787(2) 0.5329(3) 0.2182(3) 0.0539(14) Uani 1 1 d . . . . .
H19 H 0.1198 0.5404 0.2705 0.065 Uiso 1 1 calc R . . . .
C16 C -0.0453(2) 0.5113(3) 0.0623(4) 0.0739(19) Uani 1 1 d . . . . .
H16 H -0.0867 0.5043 0.0103 0.089 Uiso 1 1 calc R . . . .
C10 C 0.0499(2) 0.2428(3) 0.0604(3) 0.0595(15) Uani 1 1 d . . . . .
H10 H 0.0871 0.2450 0.1171 0.071 Uiso 1 1 calc R . . . .
C18 C 0.0286(3) 0.5740(3) 0.1917(3) 0.0668(17) Uani 1 1 d . . . . .
H18 H 0.0362 0.6097 0.2261 0.080 Uiso 1 1 calc R . . . .
C11 C 0.0261(3) 0.1766(3) 0.0208(4) 0.0698(17) Uani 1 1 d . . . . .
H11 H 0.0470 0.1343 0.0503 0.084 Uiso 1 1 calc R . . . .
C17 C -0.0339(3) 0.5624(3) 0.1130(4) 0.0773(19) Uani 1 1 d . . . . .
H17 H -0.0674 0.5902 0.0959 0.093 Uiso 1 1 calc R . . . .
C12 C -0.0288(3) 0.1750(4) -0.0627(4) 0.077(2) Uani 1 1 d . . . . .
C37 C 0.4458(2) 0.3002(3) 0.5807(3) 0.0665(17) Uani 1 1 d . . . . .
H37 H 0.4767 0.2662 0.6186 0.080 Uiso 1 1 calc R . . . .
C50 C 0.1290(2) 0.1224(3) 0.3316(3) 0.0557(14) Uani 1 1 d . . . . .
H50 H 0.1286 0.1463 0.3668 0.067 Uiso 1 1 calc R . . . .
C52 C 0.1127(3) 0.0154(3) 0.2622(3) 0.0664(16) Uani 1 1 d . . . . .
H52 H 0.1019 -0.0330 0.2506 0.080 Uiso 1 1 calc R . . . .
C54 C 0.1466(2) 0.1222(3) 0.2462(3) 0.0562(14) Uani 1 1 d . . . . .
H54 H 0.1585 0.1462 0.2235 0.067 Uiso 1 1 calc R . . . .
C53 C 0.1292(3) 0.0508(3) 0.2274(4) 0.0645(15) Uani 1 1 d . . . . .
H53 H 0.1287 0.0269 0.1914 0.077 Uiso 1 1 calc R . . . .
C51 C 0.1119(3) 0.0502(3) 0.3133(4) 0.0680(16) Uani 1 1 d . . . . .
H51 H 0.1000 0.0260 0.3359 0.082 Uiso 1 1 calc R . . . .
C36 C 0.4570(3) 0.3707(3) 0.6036(3) 0.0662(17) Uani 1 1 d . . . . .
H36 H 0.4952 0.3847 0.6564 0.079 Uiso 1 1 calc R . . . .
C13 C -0.0592(3) 0.2356(4) -0.1086(4) 0.077(2) Uani 1 1 d . . . . .
H13 H -0.0948 0.2332 -0.1658 0.093 Uiso 1 1 calc R . . . .
C32 C 0.3995(5) 0.7388(4) 0.6200(5) 0.095(2) Uani 1 1 d . . . . .
C33 C 0.4501(4) 0.7098(4) 0.6394(4) 0.096(2) Uani 1 1 d . . . . .
H33 H 0.4890 0.7339 0.6745 0.116 Uiso 1 1 calc R . . . .
C31 C 0.3418(4) 0.7071(4) 0.5684(4) 0.087(2) Uani 1 1 d . . . . .
H31 H 0.3080 0.7281 0.5570 0.105 Uiso 1 1 calc R . . . .
F2 F -0.05202(17) 0.1096(2) -0.1000(2) 0.1131(15) Uani 1 1 d . . . . .
F4 F 0.4073(3) 0.8037(2) 0.6543(3) 0.160(2) 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 N3 2.068(3) . ?
Ir1 N1 2.069(3) . ?
Ir1 O1 2.148(3) . ?
Ir1 C21 1.992(5) . ?
Ir1 N5 2.139(4) . ?
Ir1 C1 1.985(4) . ?
N3 C27 1.360(5) . ?
N3 C40 1.369(6) . ?
N1 C7 1.341(5) . ?
N1 C20 1.381(5) . ?
O1 C41 1.299(5) . ?
N6 N5 1.406(5) . ?
N6 C48 1.285(5) . ?
O2 C48 1.369(5) . ?
O2 C47 1.355(5) . ?
F1 C3 1.364(5) . ?
C21 C26 1.409(6) . ?
C21 C22 1.398(6) . ?
N5 C47 1.306(5) . ?
F3 C23 1.358(5) . ?
C27 C26 1.450(6) . ?
C27 C28 1.444(6) . ?
C1 C6 1.416(5) . ?
C1 C2 1.405(6) . ?
C5 C6 1.403(6) . ?
C5 C4 1.361(6) . ?
C26 C25 1.406(6) . ?
C6 C7 1.459(6) . ?
C25 C24 1.380(6) . ?
C23 C24 1.365(6) . ?
C23 C22 1.371(6) . ?
C46 C41 1.417(7) . ?
C46 C45 1.401(6) . ?
C46 C47 1.432(6) . ?
C2 C3 1.363(6) . ?
C7 C8 1.442(6) . ?
C48 C49 1.456(6) . ?
C4 C3 1.375(6) . ?
C41 C42 1.417(6) . ?
C28 C29 1.485(7) . ?
C28 N4 1.316(6) . ?
N2 C15 1.361(6) . ?
N2 C8 1.300(6) . ?
C40 C35 1.414(6) . ?
C40 C39 1.393(7) . ?
C35 N4 1.351(6) . ?
C35 C36 1.405(7) . ?
C49 C50 1.367(6) . ?
C49 C54 1.380(6) . ?
C29 C34 1.388(6) . ?
C29 C30 1.357(7) . ?
C15 C20 1.422(6) . ?
C15 C16 1.411(7) . ?
C39 C38 1.382(6) . ?
C38 C37 1.378(7) . ?
C9 C8 1.482(7) . ?
C9 C14 1.384(6) . ?
C9 C10 1.381(7) . ?
C45 C44 1.360(7) . ?
C34 C33 1.378(8) . ?
C43 C42 1.357(6) . ?
C43 C44 1.385(7) . ?
C30 C31 1.398(8) . ?
C20 C19 1.390(6) . ?
C14 C13 1.375(8) . ?
C19 C18 1.380(6) . ?
C16 C17 1.348(7) . ?
C10 C11 1.391(7) . ?
C18 C17 1.407(7) . ?
C11 C12 1.371(7) . ?
C12 C13 1.358(9) . ?
C12 F2 1.361(7) . ?
C37 C36 1.365(7) . ?
C50 C51 1.394(7) . ?
C52 C53 1.374(7) . ?
C52 C51 1.357(7) . ?
C54 C53 1.381(7) . ?
C32 C33 1.349(10) . ?
C32 C31 1.346(9) . ?
C32 F4 1.370(8) . ?

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
N3 Ir1 N1 174.96(14) . . ?
N3 Ir1 O1 79.13(13) . . ?
N3 Ir1 N5 98.16(14) . . ?
N1 Ir1 O1 100.22(13) . . ?
N1 Ir1 N5 86.72(14) . . ?
C21 Ir1 N3 80.30(16) . . ?
C21 Ir1 N1 94.69(16) . . ?
C21 Ir1 O1 87.09(15) . . ?
C21 Ir1 N5 171.78(15) . . ?
N5 Ir1 O1 84.68(13) . . ?
C1 Ir1 N3 101.18(16) . . ?
C1 Ir1 N1 79.50(16) . . ?
C1 Ir1 O1 179.59(15) . . ?
C1 Ir1 C21 93.22(17) . . ?
C1 Ir1 N5 95.00(15) . . ?
C27 N3 Ir1 109.5(3) . . ?
C27 N3 C40 119.0(4) . . ?
C40 N3 Ir1 130.7(3) . . ?
C7 N1 Ir1 113.3(3) . . ?
C7 N1 C20 119.2(4) . . ?
C20 N1 Ir1 127.5(3) . . ?
C41 O1 Ir1 130.4(3) . . ?
C48 N6 N5 105.4(4) . . ?
C47 O2 C48 104.3(4) . . ?
C26 C21 Ir1 112.1(3) . . ?
C22 C21 Ir1 129.2(3) . . ?
C22 C21 C26 118.5(4) . . ?
N6 N5 Ir1 125.7(3) . . ?
C47 N5 Ir1 126.1(3) . . ?
C47 N5 N6 107.9(4) . . ?
N3 C27 C26 115.2(4) . . ?
N3 C27 C28 118.1(4) . . ?
C28 C27 C26 126.6(4) . . ?
C6 C1 Ir1 114.6(3) . . ?
C2 C1 Ir1 128.5(3) . . ?
C2 C1 C6 116.9(4) . . ?
C4 C5 C6 120.3(4) . . ?
C21 C26 C27 114.4(4) . . ?
C25 C26 C21 120.8(4) . . ?
C25 C26 C27 124.1(4) . . ?
C1 C6 C7 113.9(4) . . ?
C5 C6 C1 121.2(4) . . ?
C5 C6 C7 124.4(4) . . ?
C24 C25 C26 119.5(4) . . ?
F3 C23 C24 118.0(5) . . ?
F3 C23 C22 117.6(5) . . ?
C24 C23 C22 124.4(5) . . ?
C41 C46 C47 121.3(4) . . ?
C45 C46 C41 120.1(5) . . ?
C45 C46 C47 118.5(5) . . ?
C3 C2 C1 119.5(4) . . ?
N1 C7 C6 114.1(4) . . ?
N1 C7 C8 118.7(4) . . ?
C8 C7 C6 126.9(4) . . ?
N6 C48 O2 112.3(4) . . ?
N6 C48 C49 129.7(5) . . ?
O2 C48 C49 118.0(4) . . ?
C5 C4 C3 118.2(4) . . ?
F1 C3 C4 117.9(4) . . ?
C2 C3 F1 118.3(4) . . ?
C2 C3 C4 123.9(4) . . ?
O1 C41 C46 125.6(4) . . ?
O1 C41 C42 118.7(4) . . ?
C46 C41 C42 115.7(4) . . ?
C27 C28 C29 121.6(5) . . ?
N4 C28 C27 121.6(5) . . ?
N4 C28 C29 116.4(4) . . ?
C8 N2 C15 117.7(4) . . ?
N3 C40 C35 118.9(5) . . ?
N3 C40 C39 121.3(4) . . ?
C39 C40 C35 119.8(5) . . ?
N4 C35 C40 121.8(5) . . ?
N4 C35 C36 118.3(5) . . ?
C36 C35 C40 119.7(5) . . ?
C50 C49 C48 121.8(5) . . ?
C50 C49 C54 119.2(5) . . ?
C54 C49 C48 118.9(5) . . ?
C34 C29 C28 119.6(5) . . ?
C30 C29 C28 120.4(5) . . ?
C30 C29 C34 119.8(5) . . ?
N2 C15 C20 122.0(5) . . ?
N2 C15 C16 119.3(5) . . ?
C16 C15 C20 118.4(5) . . ?
C38 C39 C40 119.0(5) . . ?
C37 C38 C39 121.0(5) . . ?
C28 N4 C35 118.3(4) . . ?
C14 C9 C8 120.9(5) . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 C14 118.4(5) . . ?
C44 C45 C46 121.8(5) . . ?
C23 C24 C25 118.4(5) . . ?
C33 C34 C29 119.5(6) . . ?
C42 C43 C44 120.5(5) . . ?
C43 C42 C41 122.9(5) . . ?
C23 C22 C21 118.4(4) . . ?
C29 C30 C31 120.4(6) . . ?
N1 C20 C15 117.8(4) . . ?
N1 C20 C19 122.2(4) . . ?
C19 C20 C15 119.9(4) . . ?
O2 C47 C46 119.4(4) . . ?
N5 C47 O2 110.0(4) . . ?
N5 C47 C46 130.6(5) . . ?
C7 C8 C9 122.4(4) . . ?
N2 C8 C7 122.1(5) . . ?
N2 C8 C9 115.0(4) . . ?
C45 C44 C43 119.0(5) . . ?
C13 C14 C9 121.6(6) . . ?
C18 C19 C20 119.8(5) . . ?
C17 C16 C15 121.2(5) . . ?
C9 C10 C11 120.6(5) . . ?
C19 C18 C17 120.6(5) . . ?
C12 C11 C10 118.4(6) . . ?
C16 C17 C18 120.1(5) . . ?
C13 C12 C11 122.5(6) . . ?
C13 C12 F2 120.0(6) . . ?
F2 C12 C11 117.6(7) . . ?
C36 C37 C38 121.4(5) . . ?
C49 C50 C51 120.5(5) . . ?
C51 C52 C53 120.7(5) . . ?
C49 C54 C53 120.5(5) . . ?
C52 C53 C54 119.5(5) . . ?
C52 C51 C50 119.6(5) . . ?
C37 C36 C35 119.1(5) . . ?
C12 C13 C14 118.3(6) . . ?
C33 C32 F4 118.4(8) . . ?
C31 C32 C33 123.0(7) . . ?
C31 C32 F4 118.6(8) . . ?
C32 C33 C34 119.1(7) . . ?
C32 C31 C30 118.1(7) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 30.4 0.0 ?
2 0.000 -0.050 0.250 13.9 0.0 ?
3 0.000 0.000 0.500 30.4 0.0 ?
4 0.000 0.050 0.750 13.9 0.0 ?
5 0.000 0.351 0.250 122.4 36.9 ?
6 0.000 0.649 0.750 122.4 37.0 ?
7 0.178 0.320 0.829 28.4 0.1 ?
8 0.178 0.680 0.329 28.4 0.0 ?
9 0.322 0.180 0.171 28.4 1.2 ?
10 0.322 0.820 0.671 28.4 1.9 ?
11 0.500 0.149 0.750 122.4 37.0 ?
12 0.500 0.500 1.000 30.4 0.0 ?
13 0.500 0.500 0.500 30.4 0.0 ?
14 0.500 0.851 0.250 122.4 36.9 ?
15 0.500 0.450 0.250 13.9 0.0 ?
16 0.500 0.550 0.750 13.9 0.0 ?
17 0.678 0.180 0.329 28.4 0.0 ?
18 0.678 0.820 0.829 28.4 0.1 ?
19 0.822 0.320 0.671 28.4 1.9 ?
20 0.822 0.680 0.171 28.4 1.2 ?


_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_1_sq
_database_code_depnum_ccdc_archive 'CCDC 1535471'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-07-19 downloaded from the CCDC.
;
_audit_creation_date             2017-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C54 H35 Ir N6 O2'
_chemical_formula_sum            'C54 H35 Ir N6 O2'
_chemical_formula_weight         992.08
_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'
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'

_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                   11.3469(19)
_cell_length_b                   31.314(5)
_cell_length_c                   13.335(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.451(3)
_cell_angle_gamma                90
_cell_volume                     4439.4(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5855
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.594
_shelx_estimated_absorpt_T_min   0.492
_exptl_absorpt_coefficient_mu    3.057
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24108
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         1.755
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6215
_reflns_number_total             7779
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         5.635
_refine_diff_density_min         -6.532
_refine_diff_density_rms         0.256
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         7779
_refine_ls_number_restraints     360
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.1040
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+257.0153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2567
_refine_ls_wR_factor_ref         0.2655
_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(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq,
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq,
Uanis(C47) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C50)
\\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq,
Uanis(C54) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(N4) \\sim
Ueq, Uanis(N5) \\sim Ueq, Uanis(N6) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C40) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
3.a Fixed occupancy and ADP/Uiso:
 N3
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24),
  C25(H25), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C36(H36),
 C37(H37), C38(H38), C39(H39), C42(H42), C43(H43), C44(H44), C45(H45), C50(H50),
  C51(H51), C52(H52), C53(H53), C54(H54)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6178(16) 0.1127(5) 0.3226(14) 0.032(4) Uani 1 1 d . U . A 1
C2 C 0.679(2) 0.0946(7) 0.4272(17) 0.047(5) Uani 1 1 d . U . A 1
H2 H 0.7647 0.0887 0.4509 0.057 Uiso 1 1 calc R . . A 1
C3 C 0.611(2) 0.0860(7) 0.4916(17) 0.049(5) Uani 1 1 d . U . A 1
H3 H 0.6494 0.0718 0.5561 0.059 Uiso 1 1 calc R . . A 1
C4 C 0.484(2) 0.0981(7) 0.4625(18) 0.050(5) Uani 1 1 d . U . A 1
H4 H 0.4386 0.0925 0.5072 0.061 Uiso 1 1 calc R . . A 1
C5 C 0.430(2) 0.1180(6) 0.3693(17) 0.046(5) Uani 1 1 d . U . A 1
H5 H 0.3480 0.1278 0.3512 0.055 Uiso 1 1 calc R . . A 1
C6 C 0.494(2) 0.1244(8) 0.298(2) 0.059(6) Uani 1 1 d . U . A 1
C7 C 0.4360(19) 0.1400(6) 0.1899(17) 0.046(5) Uani 1 1 d . U . . .
C8 C 0.314(2) 0.1617(7) 0.1416(17) 0.048(5) Uani 1 1 d . U . . .
C9 C 0.2549(19) 0.1870(6) 0.2051(18) 0.047(5) Uani 1 1 d . U . . .
C10 C 0.332(2) 0.2120(7) 0.289(2) 0.058(6) Uani 1 1 d . U . . .
H10 H 0.4188 0.2108 0.3088 0.070 Uiso 1 1 calc R . . . .
C11 C 0.275(2) 0.2393(8) 0.345(2) 0.062(6) Uani 1 1 d . U . . .
H11 H 0.3249 0.2558 0.4018 0.074 Uiso 1 1 calc R . . . .
C12 C 0.141(3) 0.2413(9) 0.312(2) 0.069(7) Uani 1 1 d . U . . .
H12 H 0.1022 0.2599 0.3450 0.083 Uiso 1 1 calc R . . . .
C13 C 0.068(2) 0.2144(9) 0.227(2) 0.068(7) Uani 1 1 d . U . . .
H13 H -0.0191 0.2150 0.2074 0.081 Uiso 1 1 calc R . . . .
C14 C 0.120(2) 0.1883(8) 0.175(2) 0.061(6) Uani 1 1 d . U . . .
H14 H 0.0698 0.1711 0.1199 0.073 Uiso 1 1 calc R . . . .
C15 C 0.317(2) 0.1470(8) -0.0252(19) 0.057(6) Uani 1 1 d . U . . .
C16 C 0.251(3) 0.1446(8) -0.140(2) 0.066(7) Uani 1 1 d . U . . .
H16 H 0.1673 0.1524 -0.1701 0.080 Uiso 1 1 calc R . . . .
C17 C 0.309(3) 0.1321(9) -0.199(2) 0.080(8) Uani 1 1 d . U . . .
H17 H 0.2674 0.1333 -0.2731 0.096 Uiso 1 1 calc R . . . .
C18 C 0.440(3) 0.1154(8) -0.161(2) 0.067(7) Uani 1 1 d . U . . .
H18 H 0.4779 0.1047 -0.2070 0.081 Uiso 1 1 calc R . . . .
C19 C 0.499(2) 0.1170(7) -0.0525(18) 0.054(6) Uani 1 1 d . U . . .
H19 H 0.5828 0.1083 -0.0273 0.065 Uiso 1 1 calc R . . . .
C20 C 0.4484(18) 0.1303(6) 0.0278(17) 0.044(5) Uani 1 1 d . U . . .
C21 C 0.7132(18) 0.0660(6) 0.1865(15) 0.037(4) Uani 1 1 d . U . . .
C22 C 0.620(2) 0.0356(7) 0.1388(17) 0.049(5) Uani 1 1 d . U . . .
H22 H 0.5360 0.0443 0.1151 0.059 Uiso 1 1 calc R . . . .
C23 C 0.645(2) -0.0049(8) 0.126(2) 0.063(6) Uani 1 1 d . U . . .
H23 H 0.5800 -0.0242 0.0951 0.076 Uiso 1 1 calc R . . . .
C24 C 0.776(2) -0.0188(8) 0.160(2) 0.067(7) Uani 1 1 d . U . . .
H24 H 0.7956 -0.0472 0.1536 0.080 Uiso 1 1 calc R . . . .
C25 C 0.870(2) 0.0110(6) 0.2026(17) 0.046(5) Uani 1 1 d . U . . .
H25 H 0.9536 0.0029 0.2205 0.055 Uiso 1 1 calc R . . . .
C26 C 0.841(2) 0.0528(7) 0.2187(17) 0.046(5) Uani 1 1 d . U . . .
C27 C 0.9319(17) 0.0843(6) 0.2754(15) 0.036(4) Uani 1 1 d . U . . .
C28 C 1.0668(18) 0.0822(6) 0.3083(16) 0.040(4) Uani 1 1 d . U . . .
C29 C 1.129(2) 0.0540(7) 0.2492(19) 0.052(5) Uani 1 1 d . U . . .
C30 C 1.091(3) 0.0539(9) 0.139(2) 0.073(7) Uani 1 1 d . U . . .
H30 H 1.0206 0.0696 0.1003 0.088 Uiso 1 1 calc R . . . .
C31 C 1.152(3) 0.0326(11) 0.085(3) 0.093(9) Uani 1 1 d . U . . .
H31 H 1.1230 0.0328 0.0106 0.111 Uiso 1 1 calc R . . . .
C32 C 1.253(3) 0.0115(10) 0.139(2) 0.081(8) Uani 1 1 d . U . . .
H32 H 1.2958 -0.0026 0.1012 0.097 Uiso 1 1 calc R . . . .
C33 C 1.301(3) 0.0085(10) 0.251(3) 0.083(8) Uani 1 1 d . U . . .
H33 H 1.3726 -0.0076 0.2869 0.099 Uiso 1 1 calc R . . . .
C34 C 1.235(2) 0.0314(8) 0.308(2) 0.064(6) Uani 1 1 d . U . . .
H34 H 1.2631 0.0312 0.3824 0.077 Uiso 1 1 calc R . . . .
C35 C 1.0853(16) 0.1373(5) 0.4191(15) 0.033(4) Uani 1 1 d . U . . .
C36 C 1.166(2) 0.1638(7) 0.5068(16) 0.047(5) Uani 1 1 d . U . . .
H36 H 1.2517 0.1575 0.5382 0.056 Uiso 1 1 calc R . . . .
C37 C 1.115(2) 0.1984(7) 0.5429(16) 0.046(5) Uani 1 1 d . U . . .
H37 H 1.1658 0.2157 0.5975 0.055 Uiso 1 1 calc R . . . .
C38 C 0.9877(19) 0.2072(7) 0.4978(16) 0.044(5) Uani 1 1 d . U . . .
H38 H 0.9551 0.2303 0.5234 0.052 Uiso 1 1 calc R . . . .
C39 C 0.9076(19) 0.1829(6) 0.4165(15) 0.039(4) Uani 1 1 d . U . . .
H39 H 0.8226 0.1895 0.3861 0.047 Uiso 1 1 calc R . . . .
C40 C 0.9578(14) 0.1486(5) 0.3822(12) 0.020(3) Uani 1 1 d . U . . .
C41 C 0.6426(18) 0.2256(6) 0.1717(15) 0.037(4) Uani 1 1 d . U . . .
C42 C 0.5868(19) 0.2633(7) 0.1925(17) 0.047(5) Uani 1 1 d . U . . .
H42 H 0.5610 0.2645 0.2514 0.057 Uiso 1 1 calc R . . . .
C43 C 0.570(2) 0.2985(8) 0.126(2) 0.064(6) Uani 1 1 d . U . . .
H43 H 0.5360 0.3234 0.1426 0.076 Uiso 1 1 calc R . . . .
C44 C 0.603(2) 0.2973(8) 0.037(2) 0.063(6) Uani 1 1 d . U . . .
H44 H 0.5856 0.3208 -0.0085 0.075 Uiso 1 1 calc R . . . .
C45 C 0.657(2) 0.2645(7) 0.014(2) 0.057(6) Uani 1 1 d . U . . .
H45 H 0.6820 0.2653 -0.0454 0.068 Uiso 1 1 calc R . . . .
C46 C 0.6797(18) 0.2260(6) 0.0803(16) 0.042(5) Uani 1 1 d . U . . .
C47 C 0.7372(17) 0.1897(6) 0.0505(14) 0.035(4) Uani 1 1 d . U . B 1
C48 C 0.8221(18) 0.1520(6) -0.0410(16) 0.041(4) Uani 1 1 d . U . B 1
N5 N 0.7549(15) 0.1519(5) 0.0892(12) 0.038(4) Uani 1 1 d . U . B 1
N6 N 0.8099(16) 0.1272(6) 0.0303(13) 0.048(4) Uani 1 1 d . U . B 1
O2 O 0.7767(13) 0.1919(4) -0.0347(11) 0.047(3) Uani 1 1 d . . . B 1
C49 C 0.862(2) 0.1433(7) -0.1327(17) 0.047(5) Uani 1 1 d . U . . .
C50 C 0.876(2) 0.1766(8) -0.1940(19) 0.058(6) Uani 1 1 d . U . . .
H50 H 0.8661 0.2047 -0.1756 0.069 Uiso 1 1 calc R . . . .
C51 C 0.906(2) 0.1669(9) -0.288(2) 0.066(7) Uani 1 1 d . U . . .
H51 H 0.9100 0.1888 -0.3342 0.079 Uiso 1 1 calc R . . . .
C52 C 0.927(3) 0.1270(9) -0.309(2) 0.072(7) Uani 1 1 d . U . . .
H52 H 0.9473 0.1210 -0.3699 0.086 Uiso 1 1 calc R . . . .
C53 C 0.920(3) 0.0932(10) -0.241(2) 0.081(8) Uani 1 1 d . U . . .
H53 H 0.9373 0.0654 -0.2550 0.097 Uiso 1 1 calc R . . . .
C54 C 0.886(2) 0.1021(8) -0.1520(19) 0.057(6) Uani 1 1 d . U . . .
H54 H 0.8808 0.0803 -0.1066 0.068 Uiso 1 1 calc R . . . .
Ir1 Ir 0.69093(7) 0.12714(2) 0.21242(6) 0.0308(2) Uani 1 1 d . . . . .
N1 N 0.5003(16) 0.1340(5) 0.1217(14) 0.042(4) Uani 1 1 d . U . . .
N2 N 0.2551(18) 0.1631(6) 0.0364(16) 0.057(5) Uani 1 1 d . U . . .
N3 N 0.8792(10) 0.1195(3) 0.3005(8) 0.010 Uani 1 1 d . U . . .
N4 N 1.1406(15) 0.1052(5) 0.3848(14) 0.044(4) Uani 1 1 d . U . . .
O1 O 0.6620(12) 0.1944(4) 0.2396(10) 0.037(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
C1 C2 1.44(3) . ?
C1 C6 1.38(3) . ?
C1 Ir1 1.976(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.37(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.41(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.33(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.40(3) . ?
C6 C7 1.44(3) . ?
C7 C8 1.47(3) . ?
C7 N1 1.36(3) . ?
C8 C9 1.48(3) . ?
C8 N2 1.33(3) . ?
C9 C10 1.40(3) . ?
C9 C14 1.44(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.42(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.43(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.42(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.34(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.46(3) . ?
C15 C20 1.51(3) . ?
C15 N2 1.35(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.25(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.48(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.37(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.44(3) . ?
C20 N1 1.19(3) . ?
C21 C22 1.40(3) . ?
C21 C26 1.42(3) . ?
C21 Ir1 1.977(18) . ?
C22 H22 0.9300 . ?
C22 C23 1.32(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.46(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.38(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.38(3) . ?
C26 C27 1.44(3) . ?
C27 C28 1.44(3) . ?
C27 N3 1.35(2) . ?
C28 C29 1.51(3) . ?
C28 N4 1.29(2) . ?
C29 C30 1.38(3) . ?
C29 C34 1.38(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.34(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.30(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.40(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.43(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.47(3) . ?
C35 C40 1.40(2) . ?
C35 N4 1.35(2) . ?
C36 H36 0.9300 . ?
C36 C37 1.40(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.38(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.38(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.37(2) . ?
C40 N3 1.461(18) . ?
C41 C42 1.41(3) . ?
C41 C46 1.42(3) . ?
C41 O1 1.30(2) . ?
C42 H42 0.9300 . ?
C42 C43 1.39(3) . ?
C43 H43 0.9300 . ?
C43 C44 1.36(3) . ?
C44 H44 0.9300 . ?
C44 C45 1.29(3) . ?
C45 H45 0.9300 . ?
C45 C46 1.46(3) . ?
C46 C47 1.44(3) . ?
C47 N5 1.28(2) . ?
C47 O2 1.36(2) . ?
C48 N6 1.27(2) . ?
C48 O2 1.37(2) . ?
C48 C49 1.47(3) . ?
N5 N6 1.40(2) . ?
N5 Ir1 2.159(15) . ?
C49 C50 1.37(3) . ?
C49 C54 1.36(3) . ?
C50 H50 0.9300 . ?
C50 C51 1.45(3) . ?
C51 H51 0.9300 . ?
C51 C52 1.32(4) . ?
C52 H52 0.9300 . ?
C52 C53 1.42(4) . ?
C53 H53 0.9300 . ?
C53 C54 1.39(4) . ?
C54 H54 0.9300 . ?
Ir1 N1 2.087(17) . ?
Ir1 N3 2.061(11) . ?
Ir1 O1 2.181(12) . ?

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
C2 C1 Ir1 128.6(14) . . ?
C6 C1 C2 116.3(19) . . ?
C6 C1 Ir1 114.9(14) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118(2) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 122(2) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 122(2) . . ?
C1 C6 C7 113.4(19) . . ?
C5 C6 C7 124(2) . . ?
C6 C7 C8 129(2) . . ?
N1 C7 C6 117.2(19) . . ?
N1 C7 C8 114.3(19) . . ?
C7 C8 C9 122.8(19) . . ?
N2 C8 C7 122(2) . . ?
N2 C8 C9 115.0(19) . . ?
C10 C9 C8 118.6(19) . . ?
C10 C9 C14 121(2) . . ?
C14 C9 C8 120(2) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119(2) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119(2) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 119(2) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122(3) . . ?
C14 C13 H13 118.8 . . ?
C9 C14 H14 120.3 . . ?
C13 C14 C9 119(2) . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C20 122(2) . . ?
N2 C15 C16 119(2) . . ?
N2 C15 C20 119(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 120(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 117.5 . . ?
C16 C17 C18 125(3) . . ?
C18 C17 H17 117.5 . . ?
C17 C18 H18 122.6 . . ?
C19 C18 C17 115(3) . . ?
C19 C18 H18 122.6 . . ?
C18 C19 H19 115.9 . . ?
C18 C19 C20 128(2) . . ?
C20 C19 H19 115.9 . . ?
C19 C20 C15 109.9(19) . . ?
N1 C20 C15 120(2) . . ?
N1 C20 C19 129(2) . . ?
C22 C21 C26 118.1(18) . . ?
C22 C21 Ir1 127.8(15) . . ?
C26 C21 Ir1 114.0(14) . . ?
C21 C22 H22 118.5 . . ?
C23 C22 C21 123(2) . . ?
C23 C22 H22 118.5 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119(2) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 H24 120.6 . . ?
C25 C24 C23 119(2) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 121(2) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C27 115.4(18) . . ?
C25 C26 C21 120.0(19) . . ?
C25 C26 C27 124.4(19) . . ?
C26 C27 C28 128.4(18) . . ?
N3 C27 C26 113.1(16) . . ?
N3 C27 C28 118.6(16) . . ?
C27 C28 C29 120.4(18) . . ?
N4 C28 C27 122.9(18) . . ?
N4 C28 C29 116.6(18) . . ?
C30 C29 C28 122(2) . . ?
C30 C29 C34 119(2) . . ?
C34 C29 C28 118(2) . . ?
C29 C30 H30 118.3 . . ?
C31 C30 C29 123(3) . . ?
C31 C30 H30 118.3 . . ?
C30 C31 H31 120.9 . . ?
C32 C31 C30 118(3) . . ?
C32 C31 H31 120.9 . . ?
C31 C32 H32 117.6 . . ?
C31 C32 C33 125(3) . . ?
C33 C32 H32 117.6 . . ?
C32 C33 H33 121.8 . . ?
C32 C33 C34 116(3) . . ?
C34 C33 H33 121.8 . . ?
C29 C34 C33 118(3) . . ?
C29 C34 H34 120.9 . . ?
C33 C34 H34 120.9 . . ?
C40 C35 C36 114.8(16) . . ?
N4 C35 C36 117.0(16) . . ?
N4 C35 C40 128.1(16) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 C35 119.4(18) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 119.8 . . ?
C38 C37 C36 120.4(19) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 H38 118.8 . . ?
C39 C38 C37 122.3(19) . . ?
C39 C38 H38 118.8 . . ?
C38 C39 H39 121.3 . . ?
C40 C39 C38 117.4(18) . . ?
C40 C39 H39 121.3 . . ?
C35 C40 N3 112.9(13) . . ?
C39 C40 C35 125.6(15) . . ?
C39 C40 N3 121.5(14) . . ?
C42 C41 C46 116.7(18) . . ?
O1 C41 C42 118.0(18) . . ?
O1 C41 C46 125.2(17) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 C41 121(2) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 H43 119.4 . . ?
C44 C43 C42 121(2) . . ?
C44 C43 H43 119.4 . . ?
C43 C44 H44 119.1 . . ?
C45 C44 C43 122(2) . . ?
C45 C44 H44 119.1 . . ?
C44 C45 H45 119.6 . . ?
C44 C45 C46 121(2) . . ?
C46 C45 H45 119.6 . . ?
C41 C46 C45 118.9(19) . . ?
C41 C46 C47 122.0(17) . . ?
C47 C46 C45 119.1(19) . . ?
N5 C47 C46 130.1(18) . . ?
N5 C47 O2 109.5(17) . . ?
O2 C47 C46 120.2(16) . . ?
N6 C48 O2 111.8(18) . . ?
N6 C48 C49 130.9(19) . . ?
O2 C48 C49 116.9(17) . . ?
C47 N5 N6 108.9(16) . . ?
C47 N5 Ir1 126.3(13) . . ?
N6 N5 Ir1 124.4(12) . . ?
C48 N6 N5 105.7(17) . . ?
C47 O2 C48 104.1(14) . . ?
C50 C49 C48 119(2) . . ?
C54 C49 C48 118(2) . . ?
C54 C49 C50 122(2) . . ?
C49 C50 H50 121.0 . . ?
C49 C50 C51 118(2) . . ?
C51 C50 H50 121.0 . . ?
C50 C51 H51 120.0 . . ?
C52 C51 C50 120(3) . . ?
C52 C51 H51 120.0 . . ?
C51 C52 H52 119.7 . . ?
C51 C52 C53 121(3) . . ?
C53 C52 H52 119.7 . . ?
C52 C53 H53 120.2 . . ?
C54 C53 C52 120(3) . . ?
C54 C53 H53 120.2 . . ?
C49 C54 C53 119(2) . . ?
C49 C54 H54 120.5 . . ?
C53 C54 H54 120.5 . . ?
C1 Ir1 C21 91.2(7) . . ?
C1 Ir1 N5 171.2(7) . . ?
C1 Ir1 N1 80.5(7) . . ?
C1 Ir1 N3 99.8(6) . . ?
C1 Ir1 O1 88.3(6) . . ?
C21 Ir1 N5 96.7(7) . . ?
C21 Ir1 N1 99.7(7) . . ?
C21 Ir1 N3 79.4(6) . . ?
C21 Ir1 O1 178.8(7) . . ?
N5 Ir1 O1 83.7(5) . . ?
N1 Ir1 N5 94.5(6) . . ?
N1 Ir1 O1 79.1(5) . . ?
N3 Ir1 N5 85.3(5) . . ?
N3 Ir1 N1 179.0(6) . . ?
N3 Ir1 O1 101.8(4) . . ?
C7 N1 Ir1 108.4(13) . . ?
C20 N1 C7 122.2(19) . . ?
C20 N1 Ir1 129.2(15) . . ?
C8 N2 C15 116.9(19) . . ?
C27 N3 C40 119.1(12) . . ?
C27 N3 Ir1 114.5(10) . . ?
C40 N3 Ir1 126.4(9) . . ?
C28 N4 C35 115.7(16) . . ?
C41 O1 Ir1 127.5(11) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.725 0.000 0.500 209.2 21.1 ?
2 -0.605 0.500 0.000 209.2 21.1 ?


_olex2_submission_special_instructions 'No special instructions were received'
