#------------------------------------------------------------------------------
#$Date: 2019-09-02 12:23:29 +0300 (Mon, 02 Sep 2019) $
#$Revision: 217915 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/36/7233607.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7233607
loop_
_publ_author_name
'Hong-Yan Li'
'Tian-Yi Li'
'Ming-Yu Teng'
'Qiu-Lei Xu'
'Song Zhang'
'Yi-Ming Jin'
'Xuan Liu'
'You-Xuan Zheng'
'Jing-Lin Zuo'
_publ_section_title
;
 Syntheses, photoluminescence and electroluminescence of four heteroleptic
 iridium complexes with 2-(5-phenyl-1,3,4-oxadiazol-2-yl)-phenol
 derivatives as ancillary ligands
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1116
_journal_page_last               1124
_journal_paper_doi               10.1039/C3TC31915F
_journal_volume                  2
_journal_year                    2014
_chemical_formula_moiety         'C38 H23 F6 Ir N4 O2'
_chemical_formula_sum            'C38 H23 F6 Ir N4 O2'
_chemical_formula_weight         873.82
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.2090(10)
_cell_angle_beta                 108.3910(10)
_cell_angle_gamma                110.0690(10)
_cell_formula_units_Z            4
_cell_length_a                   12.9055(5)
_cell_length_b                   15.0122(5)
_cell_length_c                   20.3242(7)
_cell_measurement_temperature    296(2)
_cell_volume                     3461.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_sigmaI/netI    0.0944
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21314
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    3.929
_exptl_absorpt_correction_T_max  0.649
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS,2000; Bruker'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.487
_refine_diff_density_min         -1.715
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1003
_refine_ls_number_reflns         13551
_refine_ls_number_restraints     616
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                9220
_reflns_number_total             13551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2014-2-1116-1.cif
_cod_data_source_block           2
_cod_database_code               7233607
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.8673(7) 0.2983(5) 0.4753(4) 0.0485(18) Uani 1 1 d U C .
C2 C 0.8792(8) 0.2433(6) 0.4232(4) 0.060(2) Uani 1 1 d U . .
H2 H 0.8139 0.1929 0.3927 0.072 Uiso 1 1 calc R . .
C3 C 0.9893(9) 0.2643(6) 0.4173(5) 0.071(2) Uani 1 1 d U B .
C4 C 1.0872(9) 0.3390(7) 0.4605(5) 0.074(3) Uani 1 1 d U . .
H4 H 1.1595 0.3515 0.4551 0.088 Uiso 1 1 calc R . .
C5 C 1.0787(8) 0.3947(6) 0.5111(5) 0.066(2) Uani 1 1 d U . .
H5 H 1.1446 0.4465 0.5397 0.079 Uiso 1 1 calc R . .
C6 C 0.9710(7) 0.3741(5) 0.5199(4) 0.0501(18) Uani 1 1 d U . .
C7 C 0.9543(7) 0.4293(5) 0.5743(4) 0.0488(18) Uani 1 1 d U . .
C8 C 1.0415(8) 0.5032(6) 0.6254(4) 0.064(2) Uani 1 1 d U . .
H8 H 1.1185 0.5247 0.6259 0.077 Uiso 1 1 calc R . .
C9 C 1.0143(9) 0.5457(6) 0.6765(5) 0.075(3) Uani 1 1 d U . .
H9 H 1.0729 0.5954 0.7114 0.090 Uiso 1 1 calc R . .
C10 C 0.9027(9) 0.5140(6) 0.6746(5) 0.074(3) Uani 1 1 d U . .
H10 H 0.8826 0.5409 0.7085 0.089 Uiso 1 1 calc R . .
C11 C 0.8179(8) 0.4407(6) 0.6215(5) 0.064(2) Uani 1 1 d U . .
H11 H 0.7405 0.4192 0.6203 0.077 Uiso 1 1 calc R . .
C12 C 0.9990(9) 0.2016(8) 0.3615(6) 0.107(4) Uani 1 1 d DU . .
C13 C 0.7427(7) 0.1867(5) 0.5501(4) 0.0488(18) Uani 1 1 d U C .
C14 C 0.8108(7) 0.1989(5) 0.6218(4) 0.057(2) Uani 1 1 d U . .
H14 H 0.8491 0.2602 0.6484 0.068 Uiso 1 1 calc R . .
C15 C 0.8211(9) 0.1198(6) 0.6531(5) 0.070(2) Uani 1 1 d U C .
C16 C 0.8889(8) 0.1377(6) 0.7278(5) 0.090(3) Uani 1 1 d DU . .
C17 C 0.7639(11) 0.0276(7) 0.6140(6) 0.095(3) Uani 1 1 d U . .
H17 H 0.7724 -0.0248 0.6348 0.114 Uiso 1 1 calc R C .
C18 C 0.6954(11) 0.0143(7) 0.5451(6) 0.092(3) Uani 1 1 d U C .
H18 H 0.6571 -0.0475 0.5193 0.110 Uiso 1 1 calc R . .
C19 C 0.6815(8) 0.0920(6) 0.5123(4) 0.061(2) Uani 1 1 d U . .
C20 C 0.6102(9) 0.0834(6) 0.4408(5) 0.069(2) Uani 1 1 d U C .
C21 C 0.5384(10) -0.0027(7) 0.3943(5) 0.093(3) Uani 1 1 d U . .
H21 H 0.5381 -0.0615 0.4073 0.111 Uiso 1 1 calc R C .
C22 C 0.4660(11) 0.0020(8) 0.3266(6) 0.108(4) Uani 1 1 d U C .
H22 H 0.4127 -0.0543 0.2960 0.129 Uiso 1 1 calc R . .
C23 C 0.4744(10) 0.0882(7) 0.3067(5) 0.088(3) Uani 1 1 d U . .
H23 H 0.4308 0.0912 0.2612 0.105 Uiso 1 1 calc R C .
C24 C 0.5482(9) 0.1726(7) 0.3542(5) 0.075(3) Uani 1 1 d U C .
H24 H 0.5522 0.2317 0.3406 0.090 Uiso 1 1 calc R . .
C25 C 0.6038(7) 0.4147(5) 0.4040(4) 0.0473(18) Uani 1 1 d U . .
C26 C 0.5947(8) 0.4697(6) 0.3475(4) 0.064(2) Uani 1 1 d U . .
H26 H 0.6528 0.4837 0.3273 0.077 Uiso 1 1 calc R . .
C27 C 0.5076(8) 0.5019(6) 0.3223(4) 0.065(2) Uani 1 1 d U . .
H27 H 0.5077 0.5381 0.2863 0.078 Uiso 1 1 calc R . .
C28 C 0.4166(8) 0.4820(6) 0.3492(4) 0.065(2) Uani 1 1 d U . .
H28 H 0.3560 0.5042 0.3312 0.077 Uiso 1 1 calc R . .
C29 C 0.4182(8) 0.4302(6) 0.4017(4) 0.059(2) Uani 1 1 d U . .
H29 H 0.3587 0.4183 0.4205 0.071 Uiso 1 1 calc R . .
C30 C 0.5067(7) 0.3933(5) 0.4292(4) 0.0450(17) Uani 1 1 d U . .
C31 C 0.5037(7) 0.3371(5) 0.4842(4) 0.0455(17) Uani 1 1 d U C .
C32 C 0.4431(8) 0.2707(5) 0.5644(4) 0.056(2) Uani 1 1 d U C .
C33 C 0.3713(10) 0.2458(7) 0.6089(5) 0.081(3) Uani 1 1 d U . .
C34 C 0.4229(11) 0.2228(8) 0.6747(6) 0.101(4) Uani 1 1 d U . .
H34 H 0.4993 0.2241 0.6885 0.121 Uiso 1 1 calc R . .
C35 C 0.3580(15) 0.1982(10) 0.7189(8) 0.142(5) Uani 1 1 d U . .
H35 H 0.3897 0.1819 0.7624 0.171 Uiso 1 1 calc R . .
C36 C 0.2459(17) 0.1985(11) 0.6968(9) 0.153(5) Uani 1 1 d U . .
H36 H 0.2014 0.1802 0.7256 0.183 Uiso 1 1 calc R . .
C37 C 0.1967(15) 0.2248(11) 0.6335(9) 0.149(4) Uani 1 1 d U . .
H37 H 0.1223 0.2277 0.6212 0.178 Uiso 1 1 calc R . .
C38 C 0.2619(12) 0.2471(9) 0.5881(7) 0.118(4) Uani 1 1 d U . .
H38 H 0.2298 0.2625 0.5444 0.141 Uiso 1 1 calc R . .
C39 C 0.4026(7) 0.3250(5) 0.0473(4) 0.0442(17) Uani 1 1 d U A .
C40 C 0.4775(7) 0.3031(5) 0.1061(4) 0.0530(19) Uani 1 1 d U . .
H40 H 0.4483 0.2755 0.1400 0.064 Uiso 1 1 calc R . .
C41 C 0.5925(8) 0.3220(6) 0.1138(5) 0.062(2) Uani 1 1 d U . .
C42 C 0.6620(8) 0.2938(6) 0.1746(5) 0.085(3) Uani 1 1 d DU . .
C43 C 0.6447(8) 0.3672(6) 0.0693(5) 0.067(2) Uani 1 1 d U . .
H43 H 0.7247 0.3831 0.0784 0.081 Uiso 1 1 calc R . .
C44 C 0.5758(7) 0.3884(5) 0.0108(5) 0.058(2) Uani 1 1 d U . .
H44 H 0.6084 0.4165 -0.0217 0.070 Uiso 1 1 calc R . .
C45 C 0.4574(7) 0.3685(5) -0.0008(4) 0.0463(18) Uani 1 1 d U . .
C46 C 0.3769(7) 0.3859(5) -0.0630(4) 0.0457(17) Uani 1 1 d U . .
C47 C 0.4034(8) 0.4217(5) -0.1205(4) 0.061(2) Uani 1 1 d U . .
H47 H 0.4797 0.4387 -0.1207 0.073 Uiso 1 1 calc R . .
C48 C 0.3193(9) 0.4321(6) -0.1759(5) 0.073(3) Uani 1 1 d U . .
H48 H 0.3381 0.4576 -0.2135 0.088 Uiso 1 1 calc R . .
C49 C 0.2058(9) 0.4047(6) -0.1764(5) 0.073(3) Uani 1 1 d U . .
H49 H 0.1467 0.4098 -0.2148 0.088 Uiso 1 1 calc R . .
C50 C 0.1809(8) 0.3700(5) -0.1196(4) 0.057(2) Uani 1 1 d U . .
H50 H 0.1045 0.3523 -0.1195 0.068 Uiso 1 1 calc R . .
C51 C 0.1921(6) 0.1731(5) -0.0144(4) 0.0405(16) Uani 1 1 d U A .
C52 C 0.1881(7) 0.1328(5) -0.0793(4) 0.0523(19) Uani 1 1 d U . .
H52 H 0.2046 0.1727 -0.1116 0.063 Uiso 1 1 calc R . .
C53 C 0.1606(8) 0.0363(6) -0.0961(4) 0.060(2) Uani 1 1 d U A .
C54 C 0.1599(7) -0.0046(5) -0.1623(4) 0.072(2) Uani 1 1 d DU . .
C55 C 0.1317(9) -0.0261(6) -0.0495(5) 0.076(3) Uani 1 1 d U . .
H55 H 0.1110 -0.0919 -0.0615 0.091 Uiso 1 1 calc R A .
C56 C 0.1343(9) 0.0106(6) 0.0136(5) 0.075(3) Uani 1 1 d U A .
H56 H 0.1131 -0.0307 0.0441 0.090 Uiso 1 1 calc R . .
C57 C 0.1679(7) 0.1084(5) 0.0330(4) 0.055(2) Uani 1 1 d U . .
C58 C 0.1831(7) 0.1526(5) 0.1016(4) 0.055(2) Uani 1 1 d U A .
C59 C 0.1672(9) 0.1046(6) 0.1571(5) 0.078(3) Uani 1 1 d U . .
H59 H 0.1408 0.0379 0.1515 0.094 Uiso 1 1 calc R A .
C60 C 0.1917(9) 0.1585(7) 0.2208(5) 0.084(3) Uani 1 1 d U A .
H60 H 0.1800 0.1273 0.2580 0.100 Uiso 1 1 calc R . .
C61 C 0.2321(9) 0.2552(6) 0.2297(5) 0.072(3) Uani 1 1 d U . .
H61 H 0.2510 0.2909 0.2732 0.086 Uiso 1 1 calc R A .
C62 C 0.2447(8) 0.2997(6) 0.1739(4) 0.064(2) Uani 1 1 d U A .
H62 H 0.2710 0.3665 0.1795 0.077 Uiso 1 1 calc R . .
C63 C 0.2237(7) 0.4899(5) 0.0957(4) 0.0526(19) Uani 1 1 d U . .
C64 C 0.2838(8) 0.5800(5) 0.1461(4) 0.059(2) Uani 1 1 d U . .
H64 H 0.3654 0.6092 0.1607 0.071 Uiso 1 1 calc R . .
C65 C 0.2239(9) 0.6220(6) 0.1721(5) 0.074(3) Uani 1 1 d U . .
H65 H 0.2650 0.6802 0.2027 0.089 Uiso 1 1 calc R . .
C66 C 0.1033(9) 0.5801(7) 0.1543(5) 0.079(3) Uani 1 1 d U . .
H66 H 0.0643 0.6083 0.1745 0.094 Uiso 1 1 calc R . .
C67 C 0.0423(8) 0.4978(6) 0.1072(5) 0.067(2) Uani 1 1 d U . .
H67 H -0.0393 0.4714 0.0941 0.080 Uiso 1 1 calc R . .
C68 C 0.0982(7) 0.4514(5) 0.0778(4) 0.0513(19) Uani 1 1 d U . .
C69 C 0.0294(7) 0.3623(5) 0.0295(4) 0.0455(17) Uani 1 1 d U A .
C70 C -0.1260(7) 0.2452(5) -0.0329(4) 0.0544(19) Uani 1 1 d U A .
C71 C -0.2519(8) 0.1850(5) -0.0580(5) 0.068(2) Uani 1 1 d DU . .
C72 C -0.3196(12) 0.1923(9) -0.0224(8) 0.125(4) Uani 1 1 d U . .
H72 H -0.2875 0.2373 0.0185 0.150 Uiso 1 1 calc R . .
C73 C -0.4418(13) 0.1317(11) -0.0464(9) 0.145(5) Uani 1 1 d U . .
H73 H -0.4903 0.1402 -0.0234 0.174 Uiso 1 1 calc R . .
C74 C -0.4857(13) 0.0621(10) -0.1026(8) 0.128(4) Uani 1 1 d U . .
H74 H -0.5654 0.0235 -0.1196 0.154 Uiso 1 1 calc R . .
C75 C -0.4164(13) 0.0492(10) -0.1331(8) 0.128(5) Uani 1 1 d U . .
H75 H -0.4468 -0.0037 -0.1685 0.154 Uiso 1 1 calc R . .
C76 C -0.2989(10) 0.1100(7) -0.1159(5) 0.099(3) Uani 1 1 d DU . .
H76 H -0.2535 0.1015 -0.1414 0.119 Uiso 1 1 calc R . .
F1 F 0.6165(8) 0.2043(6) 0.1858(5) 0.175(4) Uani 1 1 d DU . .
F2 F 0.7679(7) 0.2963(6) 0.1764(4) 0.134(2) Uani 1 1 d DU . .
F3 F 0.6879(8) 0.3447(6) 0.2374(4) 0.146(3) Uani 1 1 d DU . .
F4 F 0.2563(13) 0.0457(11) -0.1781(9) 0.099(6) Uani 0.52(2) 1 d PDU A 1
F5 F 0.156(2) -0.0949(9) -0.1660(9) 0.114(6) Uani 0.52(2) 1 d PDU A 1
F6 F 0.0722(13) -0.0006(14) -0.2189(5) 0.096(5) Uani 0.52(2) 1 d PDU A 1
F4' F 0.207(2) 0.0606(10) -0.1988(9) 0.101(6) Uani 0.48(2) 1 d PDU A 2
F5' F 0.2224(16) -0.0621(12) -0.1551(8) 0.093(6) Uani 0.48(2) 1 d PDU A 2
F6' F 0.0512(9) -0.0605(16) -0.2072(8) 0.103(6) Uani 0.48(2) 1 d PDU A 2
F7 F 0.9019(12) 0.1213(9) 0.3292(8) 0.120(5) Uani 0.569(16) 1 d PDU B 3
F8 F 1.0131(18) 0.2449(10) 0.3063(7) 0.129(6) Uani 0.569(16) 1 d PDU B 3
F9 F 1.0863(17) 0.1680(16) 0.3874(9) 0.172(8) Uani 0.569(16) 1 d PDU B 3
F7' F 0.9221(19) 0.2025(17) 0.2982(7) 0.139(8) Uani 0.431(16) 1 d PDU B 4
F8' F 1.1087(13) 0.2376(15) 0.3584(12) 0.137(8) Uani 0.431(16) 1 d PDU B 4
F9' F 0.977(2) 0.1109(9) 0.3748(11) 0.123(7) Uani 0.431(16) 1 d PDU B 4
F10 F 1.0058(10) 0.1594(15) 0.7416(9) 0.144(7) Uani 0.598(18) 1 d PDU C 5
F11 F 0.8982(16) 0.2174(9) 0.7672(5) 0.113(5) Uani 0.598(18) 1 d PDU C 5
F12 F 0.8544(12) 0.0669(7) 0.7625(5) 0.097(5) Uani 0.598(18) 1 d PDU C 5
F10' F 0.929(2) 0.0668(13) 0.7468(12) 0.136(9) Uani 0.402(18) 1 d PDU C 6
F11' F 0.829(2) 0.1640(19) 0.7647(10) 0.132(8) Uani 0.402(18) 1 d PDU C 6
F12' F 0.9940(13) 0.2108(12) 0.7480(9) 0.092(6) Uani 0.402(18) 1 d PDU C 6
Ir1 Ir 0.23670(2) 0.309433(18) 0.023780(14) 0.04124(10) Uani 1 1 d . . .
Ir2 Ir 0.72107(3) 0.288508(18) 0.494021(14) 0.04277(10) Uani 1 1 d . . .
N1 N 0.5723(6) 0.2932(4) 0.5151(3) 0.0485(15) Uani 1 1 d . C .
N2 N 0.5336(7) 0.2508(4) 0.5677(4) 0.0596(18) Uani 1 1 d . . .
N3 N 0.8416(6) 0.4001(4) 0.5725(3) 0.0461(15) Uani 1 1 d . C .
N4 N 0.6139(6) 0.1693(4) 0.4196(3) 0.0601(18) Uani 1 1 d . C .
N5 N 0.2198(6) 0.2494(4) 0.1106(3) 0.0502(16) Uani 1 1 d . A .
N6 N 0.0616(5) 0.3050(4) -0.0015(3) 0.0429(14) Uani 1 1 d . A .
N7 N -0.0431(6) 0.2271(4) -0.0431(3) 0.0523(16) Uani 1 1 d . . .
N8 N 0.2651(6) 0.3607(4) -0.0638(3) 0.0493(15) Uani 1 1 d . A .
O1 O 0.4168(5) 0.3241(4) 0.5130(3) 0.0585(14) Uani 1 1 d . . .
O2 O -0.0906(5) 0.3284(3) 0.0116(3) 0.0591(14) Uani 1 1 d . . .
O3 O 0.2844(4) 0.4533(3) 0.0746(3) 0.0504(13) Uani 1 1 d . A .
O4 O 0.6893(5) 0.3877(4) 0.4245(3) 0.0534(13) Uani 1 1 d . C .
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'
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
C2 C1 C6 116.9(7) . .
C2 C1 Ir2 128.6(6) . .
C6 C1 Ir2 114.4(5) . .
C3 C2 C1 119.6(8) . .
C3 C2 H2 120.2 . .
C1 C2 H2 120.2 . .
C4 C3 C2 122.0(8) . .
C4 C3 C12 120.1(9) . .
C2 C3 C12 118.0(9) . .
C5 C4 C3 120.0(9) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C4 C5 C6 119.6(9) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C5 C6 C1 121.8(7) . .
C5 C6 C7 123.3(8) . .
C1 C6 C7 115.0(7) . .
N3 C7 C8 119.9(7) . .
N3 C7 C6 114.2(6) . .
C8 C7 C6 125.9(8) . .
C7 C8 C9 119.9(9) . .
C7 C8 H8 120.1 . .
C9 C8 H8 120.1 . .
C10 C9 C8 119.1(9) . .
C10 C9 H9 120.4 . .
C8 C9 H9 120.4 . .
C9 C10 C11 118.8(9) . .
C9 C10 H10 120.6 . .
C11 C10 H10 120.6 . .
N3 C11 C10 123.0(9) . .
N3 C11 H11 118.5 . .
C10 C11 H11 118.5 . .
F9' C12 F8 134.3(13) . .
F9' C12 F8' 108.3(15) . .
F8 C12 F8' 61.9(12) . .
F9' C12 F7 51.4(11) . .
F8 C12 F7 101.4(12) . .
F8' C12 F7 134.5(13) . .
F9' C12 F9 57.8(11) . .
F8 C12 F9 109.1(14) . .
F8' C12 F9 53.1(11) . .
F7 C12 F9 104.1(13) . .
F9' C12 F7' 110.7(15) . .
F8 C12 F7' 47.0(10) . .
F8' C12 F7' 107.6(15) . .
F7 C12 F7' 61.0(11) . .
F9 C12 F7' 138.6(14) . .
F9' C12 C3 111.6(10) . .
F8 C12 C3 113.5(10) . .
F8' C12 C3 110.2(11) . .
F7 C12 C3 115.2(9) . .
F9 C12 C3 112.6(11) . .
F7' C12 C3 108.5(12) . .
C14 C13 C19 118.0(7) . .
C14 C13 Ir2 127.4(5) . .
C19 C13 Ir2 114.6(6) . .
C15 C14 C13 120.5(8) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C17 C15 C14 120.4(9) . .
C17 C15 C16 122.2(8) . .
C14 C15 C16 117.4(8) . .
F12 C16 F12' 127.2(11) . .
F12 C16 F10' 48.7(11) . .
F12' C16 F10' 97.5(14) . .
F12 C16 F10 106.5(11) . .
F12' C16 F10 36.6(9) . .
F10' C16 F10 63.8(11) . .
F12 C16 F11' 73.1(11) . .
F12' C16 F11' 104.4(14) . .
F10' C16 F11' 118.6(15) . .
F10 C16 F11' 132.0(15) . .
F12 C16 F11 104.4(10) . .
F12' C16 F11 64.4(10) . .
F10' C16 F11 130.6(13) . .
F10 C16 F11 97.8(11) . .
F11' C16 F11 41.1(9) . .
F12 C16 C15 115.5(8) . .
F12' C16 C15 114.7(10) . .
F10' C16 C15 111.8(12) . .
F10 C16 C15 113.1(10) . .
F11' C16 C15 109.4(12) . .
F11 C16 C15 117.5(9) . .
C18 C17 C15 119.8(9) . .
C18 C17 H17 120.1 . .
C15 C17 H17 120.1 . .
C17 C18 C19 121.4(9) . .
C17 C18 H18 119.3 . .
C19 C18 H18 119.3 . .
C18 C19 C13 119.9(8) . .
C18 C19 C20 124.5(8) . .
C13 C19 C20 115.7(7) . .
N4 C20 C21 120.1(9) . .
N4 C20 C19 114.0(7) . .
C21 C20 C19 125.9(9) . .
C20 C21 C22 118.2(10) . .
C20 C21 H21 120.9 . .
C22 C21 H21 120.9 . .
C23 C22 C21 120.0(11) . .
C23 C22 H22 120.0 . .
C21 C22 H22 120.0 . .
C22 C23 C24 120.0(10) . .
C22 C23 H23 120.0 . .
C24 C23 H23 120.0 . .
N4 C24 C23 120.7(9) . .
N4 C24 H24 119.7 . .
C23 C24 H24 119.7 . .
O4 C25 C26 119.3(7) . .
O4 C25 C30 127.0(6) . .
C26 C25 C30 113.6(7) . .
C27 C26 C25 123.7(8) . .
C27 C26 H26 118.2 . .
C25 C26 H26 118.2 . .
C26 C27 C28 121.2(8) . .
C26 C27 H27 119.4 . .
C28 C27 H27 119.4 . .
C29 C28 C27 118.7(8) . .
C29 C28 H28 120.7 . .
C27 C28 H28 120.7 . .
C28 C29 C30 122.3(8) . .
C28 C29 H29 118.8 . .
C30 C29 H29 118.8 . .
C29 C30 C31 120.4(7) . .
C29 C30 C25 120.4(7) . .
C31 C30 C25 119.2(7) . .
N1 C31 O1 109.8(6) . .
N1 C31 C30 130.9(7) . .
O1 C31 C30 119.3(7) . .
N2 C32 O1 112.8(6) . .
N2 C32 C33 128.2(8) . .
O1 C32 C33 119.0(8) . .
C38 C33 C34 122.0(10) . .
C38 C33 C32 121.1(10) . .
C34 C33 C32 116.9(10) . .
C35 C34 C33 119.1(13) . .
C35 C34 H34 120.4 . .
C33 C34 H34 120.4 . .
C36 C35 C34 118.4(15) . .
C36 C35 H35 120.8 . .
C34 C35 H35 120.8 . .
C35 C36 C37 122.7(15) . .
C35 C36 H36 118.7 . .
C37 C36 H36 118.7 . .
C36 C37 C38 118.5(16) . .
C36 C37 H37 120.8 . .
C38 C37 H37 120.8 . .
C33 C38 C37 119.2(13) . .
C33 C38 H38 120.4 . .
C37 C38 H38 120.4 . .
C40 C39 C45 114.8(7) . .
C40 C39 Ir1 129.6(5) . .
C45 C39 Ir1 115.6(6) . .
C41 C40 C39 120.6(7) . .
C41 C40 H40 119.7 . .
C39 C40 H40 119.7 . .
C43 C41 C40 123.9(9) . .
C43 C41 C42 119.2(9) . .
C40 C41 C42 116.9(8) . .
F1 C42 F3 101.5(9) . .
F1 C42 F2 99.5(8) . .
F3 C42 F2 102.4(8) . .
F1 C42 C41 117.2(8) . .
F3 C42 C41 116.0(8) . .
F2 C42 C41 117.3(8) . .
C41 C43 C44 117.8(8) . .
C41 C43 H43 121.1 . .
C44 C43 H43 121.1 . .
C43 C44 C45 120.7(8) . .
C43 C44 H44 119.6 . .
C45 C44 H44 119.6 . .
C44 C45 C39 122.0(8) . .
C44 C45 C46 124.1(7) . .
C39 C45 C46 113.9(7) . .
N8 C46 C47 118.9(8) . .
N8 C46 C45 114.4(6) . .
C47 C46 C45 126.7(7) . .
C48 C47 C46 120.8(8) . .
C48 C47 H47 119.6 . .
C46 C47 H47 119.6 . .
C47 C48 C49 119.6(8) . .
C47 C48 H48 120.2 . .
C49 C48 H48 120.2 . .
C50 C49 C48 119.1(9) . .
C50 C49 H49 120.4 . .
C48 C49 H49 120.4 . .
N8 C50 C49 121.3(8) . .
N8 C50 H50 119.3 . .
C49 C50 H50 119.3 . .
C52 C51 C57 116.3(6) . .
C52 C51 Ir1 129.2(5) . .
C57 C51 Ir1 114.3(5) . .
C53 C52 C51 121.6(7) . .
C53 C52 H52 119.2 . .
C51 C52 H52 119.2 . .
C52 C53 C55 120.5(8) . .
C52 C53 C54 121.5(7) . .
C55 C53 C54 118.1(7) . .
F5 C54 F4' 125.1(12) . .
F5 C54 F5' 33.7(9) . .
F4' C54 F5' 103.4(12) . .
F5 C54 F6' 73.5(10) . .
F4' C54 F6' 105.8(11) . .
F5' C54 F6' 104.2(11) . .
F5 C54 F6 108.2(11) . .
F4' C54 F6 71.1(10) . .
F5' C54 F6 129.9(11) . .
F6' C54 F6 39.2(7) . .
F5 C54 F4 104.7(12) . .
F4' C54 F4 32.3(9) . .
F5' C54 F4 75.0(10) . .
F6' C54 F4 127.9(11) . .
F6 C54 F4 101.1(11) . .
F5 C54 C53 115.1(9) . .
F4' C54 C53 114.5(9) . .
F5' C54 C53 113.9(9) . .
F6' C54 C53 113.9(9) . .
F6 C54 C53 113.2(8) . .
F4 C54 C53 113.3(9) . .
C56 C55 C53 119.3(8) . .
C56 C55 H55 120.4 . .
C53 C55 H55 120.4 . .
C55 C56 C57 121.0(8) . .
C55 C56 H56 119.5 . .
C57 C56 H56 119.5 . .
C56 C57 C51 121.1(7) . .
C56 C57 C58 123.6(7) . .
C51 C57 C58 115.3(6) . .
N5 C58 C59 119.8(7) . .
N5 C58 C57 114.3(6) . .
C59 C58 C57 125.9(7) . .
C60 C59 C58 118.5(8) . .
C60 C59 H59 120.8 . .
C58 C59 H59 120.8 . .
C61 C60 C59 121.2(8) . .
C61 C60 H60 119.4 . .
C59 C60 H60 119.4 . .
C60 C61 C62 118.8(8) . .
C60 C61 H61 120.6 . .
C62 C61 H61 120.6 . .
N5 C62 C61 121.6(7) . .
N5 C62 H62 119.2 . .
C61 C62 H62 119.2 . .
O3 C63 C68 127.1(7) . .
O3 C63 C64 119.0(8) . .
C68 C63 C64 113.8(7) . .
C65 C64 C63 122.0(8) . .
C65 C64 H64 119.0 . .
C63 C64 H64 119.0 . .
C64 C65 C66 121.5(9) . .
C64 C65 H65 119.3 . .
C66 C65 H65 119.3 . .
C67 C66 C65 119.6(9) . .
C67 C66 H66 120.2 . .
C65 C66 H66 120.2 . .
C66 C67 C68 121.9(9) . .
C66 C67 H67 119.1 . .
C68 C67 H67 119.1 . .
C67 C68 C63 121.2(7) . .
C67 C68 C69 119.7(8) . .
C63 C68 C69 119.1(7) . .
N6 C69 O2 111.3(6) . .
N6 C69 C68 130.7(7) . .
O2 C69 C68 118.1(7) . .
N7 C70 O2 114.4(7) . .
N7 C70 C71 128.5(8) . .
O2 C70 C71 116.9(7) . .
C72 C71 C76 119.0(10) . .
C72 C71 C70 120.9(9) . .
C76 C71 C70 119.7(9) . .
C71 C72 C73 120.5(12) . .
C71 C72 H72 119.8 . .
C73 C72 H72 119.8 . .
C74 C73 C72 119.4(13) . .
C74 C73 H73 120.3 . .
C72 C73 H73 120.3 . .
C75 C74 C73 119.7(15) . .
C75 C74 H74 120.2 . .
C73 C74 H74 120.2 . .
C74 C75 C76 123.8(14) . .
C74 C75 H75 118.1 . .
C76 C75 H75 118.1 . .
C75 C76 C71 117.1(10) . .
C75 C76 H76 121.4 . .
C71 C76 H76 121.4 . .
C39 Ir1 C51 88.2(3) . .
C39 Ir1 N5 94.5(3) . .
C51 Ir1 N5 80.8(3) . .
C39 Ir1 N8 80.5(3) . .
C51 Ir1 N8 94.9(2) . .
N5 Ir1 N8 173.5(2) . .
C39 Ir1 N6 175.3(2) . .
C51 Ir1 N6 96.2(2) . .
N5 Ir1 N6 88.0(2) . .
N8 Ir1 N6 97.3(2) . .
C39 Ir1 O3 92.2(2) . .
C51 Ir1 O3 174.5(2) . .
N5 Ir1 O3 93.8(2) . .
N8 Ir1 O3 90.5(2) . .
N6 Ir1 O3 83.7(2) . .
C13 Ir2 C1 87.6(3) . .
C13 Ir2 N4 80.2(3) . .
C1 Ir2 N4 95.0(3) . .
C13 Ir2 N3 94.7(3) . .
C1 Ir2 N3 80.7(3) . .
N4 Ir2 N3 173.4(3) . .
C13 Ir2 N1 96.7(3) . .
C1 Ir2 N1 174.3(2) . .
N4 Ir2 N1 89.5(3) . .
N3 Ir2 N1 95.2(2) . .
C13 Ir2 O4 174.3(2) . .
C1 Ir2 O4 91.8(2) . .
N4 Ir2 O4 94.3(2) . .
N3 Ir2 O4 90.8(2) . .
N1 Ir2 O4 84.2(2) . .
C31 N1 N2 108.3(6) . .
C31 N1 Ir2 127.1(5) . .
N2 N1 Ir2 124.6(5) . .
C32 N2 N1 105.7(6) . .
C11 N3 C7 119.3(7) . .
C11 N3 Ir2 125.0(6) . .
C7 N3 Ir2 115.7(5) . .
C24 N4 C20 120.8(7) . .
C24 N4 Ir2 123.7(6) . .
C20 N4 Ir2 115.5(6) . .
C58 N5 C62 120.1(6) . .
C58 N5 Ir1 115.2(5) . .
C62 N5 Ir1 124.6(5) . .
C69 N6 N7 106.7(6) . .
C69 N6 Ir1 125.8(5) . .
N7 N6 Ir1 126.0(4) . .
C70 N7 N6 105.2(6) . .
C50 N8 C46 120.3(6) . .
C50 N8 Ir1 124.3(5) . .
C46 N8 Ir1 115.4(5) . .
C32 O1 C31 103.3(6) . .
C70 O2 C69 102.4(6) . .
C63 O3 Ir1 129.6(5) . .
C25 O4 Ir2 130.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.394(10) .
C1 C6 1.420(10) .
C1 Ir2 1.999(7) .
C2 C3 1.392(11) .
C2 H2 0.9300 .
C3 C4 1.368(13) .
C3 C12 1.509(13) .
C4 C5 1.356(12) .
C4 H4 0.9300 .
C5 C6 1.389(11) .
C5 H5 0.9300 .
C6 C7 1.468(10) .
C7 N3 1.355(9) .
C7 C8 1.376(11) .
C8 C9 1.392(12) .
C8 H8 0.9300 .
C9 C10 1.341(12) .
C9 H9 0.9300 .
C10 C11 1.383(12) .
C10 H10 0.9300 .
C11 N3 1.315(9) .
C11 H11 0.9300 .
C12 F9' 1.348(8) .
C12 F8 1.350(8) .
C12 F8' 1.354(8) .
C12 F7 1.355(8) .
C12 F9 1.356(8) .
C12 F7' 1.359(8) .
C13 C14 1.411(11) .
C13 C19 1.414(10) .
C13 Ir2 1.985(7) .
C14 C15 1.395(11) .
C14 H14 0.9300 .
C15 C17 1.391(13) .
C15 C16 1.454(12) .
C16 F12 1.324(7) .
C16 F12' 1.345(8) .
C16 F10' 1.354(8) .
C16 F10 1.361(8) .
C16 F11' 1.361(8) .
C16 F11 1.363(8) .
C17 C18 1.363(14) .
C17 H17 0.9300 .
C18 C19 1.401(12) .
C18 H18 0.9300 .
C19 C20 1.425(12) .
C20 N4 1.366(10) .
C20 C21 1.399(12) .
C21 C22 1.417(15) .
C21 H21 0.9300 .
C22 C23 1.349(13) .
C22 H22 0.9300 .
C23 C24 1.393(12) .
C23 H23 0.9300 .
C24 N4 1.345(11) .
C24 H24 0.9300 .
C25 O4 1.260(9) .
C25 C26 1.438(10) .
C25 C30 1.441(10) .
C26 C27 1.337(12) .
C26 H26 0.9300 .
C27 C28 1.394(11) .
C27 H27 0.9300 .
C28 C29 1.343(11) .
C28 H28 0.9300 .
C29 C30 1.406(11) .
C29 H29 0.9300 .
C30 C31 1.428(10) .
C31 N1 1.302(9) .
C31 O1 1.384(8) .
C32 N2 1.285(10) .
C32 O1 1.370(9) .
C32 C33 1.459(11) .
C33 C38 1.347(16) .
C33 C34 1.409(14) .
C34 C35 1.389(15) .
C34 H34 0.9300 .
C35 C36 1.37(2) .
C35 H35 0.9300 .
C36 C37 1.38(2) .
C36 H36 0.9300 .
C37 C38 1.412(16) .
C37 H37 0.9300 .
C38 H38 0.9300 .
C39 C40 1.412(11) .
C39 C45 1.430(9) .
C39 Ir1 1.967(8) .
C40 C41 1.367(11) .
C40 H40 0.9300 .
C41 C43 1.361(11) .
C41 C42 1.454(12) .
C42 F1 1.329(7) .
C42 F3 1.343(7) .
C42 F2 1.344(7) .
C43 C44 1.364(12) .
C43 H43 0.9300 .
C44 C45 1.391(10) .
C44 H44 0.9300 .
C45 C46 1.459(11) .
C46 N8 1.355(9) .
C46 C47 1.394(10) .
C47 C48 1.353(13) .
C47 H47 0.9300 .
C48 C49 1.376(13) .
C48 H48 0.9300 .
C49 C50 1.367(11) .
C49 H49 0.9300 .
C50 N8 1.351(10) .
C50 H50 0.9300 .
C51 C52 1.409(10) .
C51 C57 1.421(9) .
C51 Ir1 1.977(7) .
C52 C53 1.368(10) .
C52 H52 0.9300 .
C53 C55 1.403(11) .
C53 C54 1.453(11) .
C54 F5 1.338(8) .
C54 F4' 1.346(8) .
C54 F5' 1.353(8) .
C54 F6' 1.353(8) .
C54 F6 1.356(8) .
C54 F4 1.359(8) .
C55 C56 1.362(12) .
C55 H55 0.9300 .
C56 C57 1.381(11) .
C56 H56 0.9300 .
C57 C58 1.447(11) .
C58 N5 1.350(9) .
C58 C59 1.393(10) .
C59 C60 1.383(12) .
C59 H59 0.9300 .
C60 C61 1.346(11) .
C60 H60 0.9300 .
C61 C62 1.365(11) .
C61 H61 0.9300 .
C62 N5 1.351(9) .
C62 H62 0.9300 .
C63 O3 1.260(9) .
C63 C68 1.435(11) .
C63 C64 1.467(10) .
C64 C65 1.357(11) .
C64 H64 0.9300 .
C65 C66 1.379(12) .
C65 H65 0.9300 .
C66 C67 1.351(11) .
C66 H66 0.9300 .
C67 C68 1.397(11) .
C67 H67 0.9300 .
C68 C69 1.440(10) .
C69 N6 1.296(9) .
C69 O2 1.370(9) .
C70 N7 1.262(10) .
C70 O2 1.359(9) .
C70 C71 1.467(11) .
C71 C72 1.328(13) .
C71 C76 1.413(7) .
C72 C73 1.431(17) .
C72 H72 0.9300 .
C73 C74 1.346(18) .
C73 H73 0.9300 .
C74 C75 1.296(16) .
C74 H74 0.9300 .
C75 C76 1.395(15) .
C75 H75 0.9300 .
C76 H76 0.9300 .
Ir1 N5 2.051(6) .
Ir1 N8 2.054(6) .
Ir1 N6 2.130(6) .
Ir1 O3 2.150(5) .
Ir2 N4 2.043(6) .
Ir2 N3 2.052(6) .
Ir2 N1 2.118(6) .
Ir2 O4 2.144(5) .
N1 N2 1.402(8) .
N6 N7 1.423(8) .
