#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:43:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180352 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/21/7202145.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_7202145
loop_
_publ_author_name
'Orselli, Enrico'
'Albuquerque, Rodrigo Q.'
'Fransen, P. Michel'
'Fröhlich, Roland'
'Janssen, Henk M.'
'De Cola, Luisa'
_publ_section_title
;
 1,2,3-Triazolyl-pyridine derivatives as chelating ligands for blue
 iridium(iii) complexes. Photophysics and electroluminescent devices
;
_journal_issue                   38
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              4579
_journal_paper_doi               10.1039/b805324c
_journal_volume                  18
_journal_year                    2008
_chemical_formula_sum            'C39 H24 F9 Ir N6 O'
_chemical_formula_weight         955.84
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.537(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.9847(2)
_cell_length_b                   16.2224(2)
_cell_length_c                   18.3429(2)
_cell_measurement_reflns_used    7346
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.41
_cell_volume                     6917.55(14)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotataing anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23852
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    3.953
_exptl_absorpt_correction_T_max  0.6833
_exptl_absorpt_correction_T_min  0.3935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.363
_refine_diff_density_min         -1.148
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0264P)²+9.5981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                6911
_reflns_number_total             8466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b805324c.txt
_cod_data_source_block           fro4438
_cod_original_cell_volume        6917.54(13)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7202145
loop_
_symmetry_equiv_pos_as_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'
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
Ir Ir -0.302115(4) 0.557059(7) 0.615203(6) 0.02315(4) Uani 1 1 d . . .
N1 N -0.25706(10) 0.56106(13) 0.74688(14) 0.0241(5) Uani 1 1 d . . .
C2 C -0.28169(13) 0.56925(18) 0.79737(19) 0.0313(7) Uani 1 1 d . . .
H2 H -0.3218 0.5763 0.7746 0.038 Uiso 1 1 calc R . .
C3 C -0.25063(14) 0.56769(19) 0.88098(19) 0.0341(7) Uani 1 1 d . . .
H3 H -0.2694 0.5733 0.9143 0.041 Uiso 1 1 calc R . .
C4 C -0.19168(14) 0.55787(18) 0.9153(2) 0.0330(7) Uani 1 1 d . . .
H4 H -0.1697 0.5563 0.9722 0.040 Uiso 1 1 calc R . .
C5 C -0.16559(13) 0.55039(18) 0.86426(18) 0.0299(6) Uani 1 1 d . . .
H5 H -0.1254 0.5447 0.8863 0.036 Uiso 1 1 calc R . .
C6 C -0.19898(12) 0.55131(16) 0.78030(17) 0.0246(6) Uani 1 1 d . . .
C7 C -0.17652(12) 0.54123(18) 0.72126(17) 0.0278(6) Uani 1 1 d . . .
N8 N -0.21493(10) 0.53409(15) 0.64162(14) 0.0284(5) Uani 1 1 d . . .
N9 N -0.18656(11) 0.52420(18) 0.59690(16) 0.0371(6) Uani 1 1 d . . .
N10 N -0.12962(11) 0.5258(2) 0.64646(17) 0.0429(7) Uani 1 1 d . . .
C11 C -0.12241(13) 0.5361(2) 0.72392(19) 0.0355(7) Uani 1 1 d . . .
C12 C -0.06479(13) 0.5455(2) 0.7941(2) 0.0375(8) Uani 1 1 d . . .
C13 C -0.03720(16) 0.6207(3) 0.8135(3) 0.0633(12) Uani 1 1 d . . .
F13 F -0.06142(12) 0.68543(19) 0.7656(2) 0.1287(15) Uani 1 1 d . . .
C14 C 0.01509(17) 0.6325(3) 0.8812(3) 0.0730(14) Uani 1 1 d . . .
F14 F 0.03950(14) 0.7071(2) 0.8978(2) 0.1389(17) Uani 1 1 d . . .
C15 C 0.04112(15) 0.5676(2) 0.9312(2) 0.0511(10) Uani 1 1 d . . .
F15 F 0.09103(9) 0.57826(17) 0.99761(15) 0.0730(7) Uani 1 1 d . . .
C16 C 0.01532(15) 0.4925(3) 0.9147(2) 0.0491(9) Uani 1 1 d . . .
F16 F 0.04029(12) 0.42942(15) 0.96580(16) 0.0820(9) Uani 1 1 d . . .
C17 C -0.03716(15) 0.4821(2) 0.8475(2) 0.0456(9) Uani 1 1 d . . .
F17 F -0.06235(12) 0.40875(16) 0.83625(16) 0.0900(10) Uani 1 1 d . . .
N21 N -0.32493(11) 0.43836(14) 0.62312(14) 0.0275(5) Uani 1 1 d . . .
C22 C -0.29152(14) 0.3723(2) 0.62945(18) 0.0373(8) Uani 1 1 d . . .
H22 H -0.2545 0.3807 0.6338 0.045 Uiso 1 1 calc R . .
C23 C -0.31018(17) 0.2932(2) 0.6298(2) 0.0476(9) Uani 1 1 d . . .
H23 H -0.2863 0.2482 0.6337 0.057 Uiso 1 1 calc R . .
C24 C -0.36426(18) 0.2805(2) 0.6242(2) 0.0535(10) Uani 1 1 d . . .
H24 H -0.3775 0.2266 0.6243 0.064 Uiso 1 1 calc R . .
C25 C -0.39870(16) 0.3469(2) 0.6185(2) 0.0458(9) Uani 1 1 d . . .
H25 H -0.4355 0.3385 0.6151 0.055 Uiso 1 1 calc R . .
C26 C -0.37877(13) 0.42722(18) 0.61775(18) 0.0307(7) Uani 1 1 d . . .
C27 C -0.41051(12) 0.5039(2) 0.60942(17) 0.0310(7) Uani 1 1 d . . .
C28 C -0.46496(13) 0.5117(2) 0.6047(2) 0.0397(8) Uani 1 1 d . . .
F28 F -0.49311(9) 0.44316(13) 0.61083(15) 0.0579(6) Uani 1 1 d . . .
C29 C -0.49304(14) 0.5859(2) 0.5948(2) 0.0460(9) Uani 1 1 d . . .
H29 H -0.5300 0.5895 0.5920 0.055 Uiso 1 1 calc R . .
C30 C -0.46411(14) 0.6540(2) 0.5892(2) 0.0461(9) Uani 1 1 d . . .
F30 F -0.49102(10) 0.72818(14) 0.57824(18) 0.0751(8) Uani 1 1 d . . .
C31 C -0.40961(13) 0.6519(2) 0.5942(2) 0.0371(7) Uani 1 1 d . . .
H31 H -0.3916 0.7008 0.5903 0.045 Uiso 1 1 calc R . .
C32 C -0.38160(12) 0.57670(19) 0.60497(17) 0.0277(6) Uani 1 1 d . . .
N41 N -0.29066(10) 0.67803(15) 0.59520(15) 0.0298(5) Uani 1 1 d . . .
C42 C -0.26444(15) 0.7338(2) 0.6543(2) 0.0402(8) Uani 1 1 d . . .
H42 H -0.2476 0.7160 0.7088 0.048 Uiso 1 1 calc R . .
C43 C -0.26116(16) 0.8159(2) 0.6384(2) 0.0505(9) Uani 1 1 d . . .
H43 H -0.2429 0.8536 0.6813 0.061 Uiso 1 1 calc R . .
C44 C -0.28516(16) 0.8422(2) 0.5584(2) 0.0492(9) Uani 1 1 d . . .
H44 H -0.2832 0.8980 0.5460 0.059 Uiso 1 1 calc R . .
C45 C -0.31185(15) 0.7858(2) 0.4973(2) 0.0433(8) Uani 1 1 d . . .
H45 H -0.3286 0.8031 0.4426 0.052 Uiso 1 1 calc R . .
C46 C -0.31431(12) 0.70268(19) 0.51567(19) 0.0332(7) Uani 1 1 d . . .
C47 C -0.34051(13) 0.63522(19) 0.45814(18) 0.0324(7) Uani 1 1 d . . .
C48 C -0.36679(15) 0.6419(2) 0.3733(2) 0.0444(8) Uani 1 1 d . . .
F48 F -0.36805(12) 0.71525(14) 0.33806(13) 0.0706(7) Uani 1 1 d . . .
C49 C -0.39127(16) 0.5763(3) 0.3221(2) 0.0498(9) Uani 1 1 d . . .
H49 H -0.4090 0.5822 0.2651 0.060 Uiso 1 1 calc R . .
C50 C -0.38832(14) 0.5017(2) 0.3587(2) 0.0430(8) Uani 1 1 d . . .
F50 F -0.41222(11) 0.43549(14) 0.30897(13) 0.0656(7) Uani 1 1 d . . .
C51 C -0.36273(13) 0.4898(2) 0.44144(19) 0.0343(7) Uani 1 1 d . . .
H51 H -0.3615 0.4370 0.4632 0.041 Uiso 1 1 calc R . .
C52 C -0.33851(12) 0.55689(17) 0.49286(17) 0.0267(6) Uani 1 1 d . . .
O61 O -0.18538(14) 0.2574(2) 0.6351(2) 0.0789(9) Uani 1 1 d . . .
C62 C -0.1741(3) 0.2707(4) 0.5698(3) 0.1020(19) Uani 1 1 d . . .
H62A H -0.1936 0.3210 0.5412 0.122 Uiso 1 1 calc R . .
H62B H -0.1887 0.2244 0.5316 0.122 Uiso 1 1 calc R . .
C63 C -0.1131(3) 0.2788(5) 0.5978(5) 0.126(3) Uani 1 1 d . . .
H63A H -0.0981 0.2314 0.5802 0.151 Uiso 1 1 calc R . .
H63B H -0.1044 0.3291 0.5758 0.151 Uiso 1 1 calc R . .
C64 C -0.0876(2) 0.2825(5) 0.6848(5) 0.125(3) Uani 1 1 d . . .
H64A H -0.0668 0.3345 0.7046 0.150 Uiso 1 1 calc R . .
H64B H -0.0607 0.2367 0.7089 0.150 Uiso 1 1 calc R . .
C65 C -0.1372(3) 0.2764(4) 0.7063(3) 0.0990(19) Uani 1 1 d . . .
H65A H -0.1298 0.2332 0.7471 0.119 Uiso 1 1 calc R . .
H65B H -0.1426 0.3289 0.7284 0.119 Uiso 1 1 calc R . .
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
_geom_angle_publ_flag
C52 Ir C32 86.83(11) . . ?
C52 Ir N21 94.10(10) . . ?
C32 Ir N21 80.64(11) . . ?
C52 Ir N41 80.46(11) . . ?
C32 Ir N41 93.27(11) . . ?
N21 Ir N41 172.09(9) . . ?
C52 Ir N8 100.15(10) . . ?
C32 Ir N8 172.93(10) . . ?
N21 Ir N8 97.61(10) . . ?
N41 Ir N8 89.04(9) . . ?
C52 Ir N1 175.63(10) . . ?
C32 Ir N1 96.90(10) . . ?
N21 Ir N1 88.76(9) . . ?
N41 Ir N1 97.01(9) . . ?
N8 Ir N1 76.17(9) . . ?
C2 N1 C6 118.3(2) . . ?
C2 N1 Ir 125.7(2) . . ?
C6 N1 Ir 115.94(18) . . ?
N1 C2 C3 122.8(3) . . ?
C2 C3 C4 119.2(3) . . ?
C3 C4 C5 118.7(3) . . ?
C4 C5 C6 119.8(3) . . ?
N1 C6 C5 121.2(3) . . ?
N1 C6 C7 114.3(2) . . ?
C5 C6 C7 124.5(3) . . ?
N8 C7 C11 106.2(3) . . ?
N8 C7 C6 117.8(2) . . ?
C11 C7 C6 136.0(3) . . ?
N9 N8 C7 109.2(2) . . ?
N9 N8 Ir 134.85(19) . . ?
C7 N8 Ir 115.25(19) . . ?
N8 N9 N10 108.9(2) . . ?
N9 N10 C11 107.8(2) . . ?
N10 C11 C7 107.8(3) . . ?
N10 C11 C12 122.3(3) . . ?
C7 C11 C12 129.7(3) . . ?
C13 C12 C17 115.5(3) . . ?
C13 C12 C11 121.5(3) . . ?
C17 C12 C11 122.9(3) . . ?
F13 C13 C12 119.3(3) . . ?
F13 C13 C14 117.9(4) . . ?
C12 C13 C14 122.9(3) . . ?
F14 C14 C15 120.3(4) . . ?
F14 C14 C13 120.3(4) . . ?
C15 C14 C13 119.4(4) . . ?
F15 C15 C16 120.0(3) . . ?
F15 C15 C14 120.2(4) . . ?
C16 C15 C14 119.8(3) . . ?
F16 C16 C15 119.4(3) . . ?
F16 C16 C17 120.5(4) . . ?
C15 C16 C17 120.1(3) . . ?
F17 C17 C16 118.0(3) . . ?
F17 C17 C12 119.5(3) . . ?
C16 C17 C12 122.4(4) . . ?
C22 N21 C26 119.8(3) . . ?
C22 N21 Ir 124.0(2) . . ?
C26 N21 Ir 116.08(19) . . ?
N21 C22 C23 121.8(3) . . ?
C22 C23 C24 119.3(3) . . ?
C25 C24 C23 119.8(3) . . ?
C24 C25 C26 119.8(3) . . ?
N21 C26 C25 119.4(3) . . ?
N21 C26 C27 113.9(3) . . ?
C25 C26 C27 126.7(3) . . ?
C28 C27 C32 118.2(3) . . ?
C28 C27 C26 126.7(3) . . ?
C32 C27 C26 115.1(3) . . ?
F28 C28 C29 116.8(3) . . ?
F28 C28 C27 119.4(3) . . ?
C29 C28 C27 123.7(3) . . ?
C30 C29 C28 116.1(3) . . ?
F30 C30 C29 117.6(3) . . ?
F30 C30 C31 118.4(3) . . ?
C29 C30 C31 124.0(3) . . ?
C30 C31 C32 119.2(3) . . ?
C31 C32 C27 118.8(3) . . ?
C31 C32 Ir 127.0(2) . . ?
C27 C32 Ir 114.2(2) . . ?
C42 N41 C46 119.4(3) . . ?
C42 N41 Ir 124.4(2) . . ?
C46 N41 Ir 116.2(2) . . ?
N41 C42 C43 122.6(3) . . ?
C42 C43 C44 118.9(3) . . ?
C45 C44 C43 119.1(3) . . ?
C44 C45 C46 120.5(3) . . ?
N41 C46 C45 119.5(3) . . ?
N41 C46 C47 113.2(3) . . ?
C45 C46 C47 127.2(3) . . ?
C48 C47 C52 118.2(3) . . ?
C48 C47 C46 125.8(3) . . ?
C52 C47 C46 115.9(3) . . ?
F48 C48 C49 116.8(3) . . ?
F48 C48 C47 119.8(3) . . ?
C49 C48 C47 123.3(3) . . ?
C50 C49 C48 116.2(3) . . ?
F50 C50 C49 117.3(3) . . ?
F50 C50 C51 118.7(3) . . ?
C49 C50 C51 124.1(3) . . ?
C50 C51 C52 119.3(3) . . ?
C51 C52 C47 118.9(3) . . ?
C51 C52 Ir 127.1(2) . . ?
C47 C52 Ir 114.0(2) . . ?
C62 O61 C65 109.5(4) . . ?
O61 C62 C63 109.5(5) . . ?
C64 C63 C62 106.9(5) . . ?
C63 C64 C65 105.3(5) . . ?
O61 C65 C64 106.7(5) . . ?
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
Ir C52 2.009(3) . ?
Ir C32 2.014(3) . ?
Ir N21 2.039(2) . ?
Ir N41 2.043(2) . ?
Ir N8 2.127(2) . ?
Ir N1 2.164(2) . ?
N1 C2 1.347(4) . ?
N1 C6 1.361(4) . ?
C2 C3 1.378(4) . ?
C3 C4 1.381(5) . ?
C4 C5 1.385(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.451(4) . ?
C7 N8 1.357(4) . ?
C7 C11 1.388(4) . ?
N8 N9 1.335(3) . ?
N9 N10 1.347(4) . ?
N10 C11 1.358(4) . ?
C11 C12 1.483(4) . ?
C12 C13 1.378(5) . ?
C12 C17 1.381(5) . ?
C13 F13 1.332(4) . ?
C13 C14 1.385(5) . ?
C14 F14 1.336(5) . ?
C14 C15 1.361(5) . ?
C15 F15 1.335(4) . ?
C15 C16 1.359(5) . ?
C16 F16 1.342(4) . ?
C16 C17 1.380(5) . ?
C17 F17 1.329(5) . ?
N21 C22 1.352(4) . ?
N21 C26 1.370(4) . ?
C22 C23 1.372(5) . ?
C23 C24 1.378(5) . ?
C24 C25 1.373(5) . ?
C25 C26 1.405(4) . ?
C26 C27 1.463(4) . ?
C27 C28 1.384(4) . ?
C27 C32 1.421(4) . ?
C28 F28 1.364(4) . ?
C28 C29 1.376(5) . ?
C29 C30 1.365(5) . ?
C30 F30 1.361(4) . ?
C30 C31 1.379(4) . ?
C31 C32 1.389(4) . ?
N41 C42 1.341(4) . ?
N41 C46 1.366(4) . ?
C42 C43 1.375(5) . ?
C43 C44 1.381(5) . ?
C44 C45 1.371(5) . ?
C45 C46 1.398(4) . ?
C46 C47 1.460(4) . ?
C47 C48 1.396(4) . ?
C47 C52 1.412(4) . ?
C48 F48 1.348(4) . ?
C48 C49 1.373(5) . ?
C49 C50 1.369(5) . ?
C50 F50 1.366(4) . ?
C50 C51 1.371(4) . ?
C51 C52 1.393(4) . ?
O61 C62 1.372(6) . ?
O61 C65 1.380(6) . ?
C62 C63 1.438(8) . ?
C63 C64 1.429(9) . ?
C64 C65 1.511(8) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C52 Ir N1 C2 152.3(12) . . . . ?
C32 Ir N1 C2 3.6(2) . . . . ?
N21 Ir N1 C2 -76.8(2) . . . . ?
N41 Ir N1 C2 97.8(2) . . . . ?
N8 Ir N1 C2 -174.9(2) . . . . ?
C52 Ir N1 C6 -30.3(14) . . . . ?
C32 Ir N1 C6 -178.89(19) . . . . ?
N21 Ir N1 C6 100.70(19) . . . . ?
N41 Ir N1 C6 -84.71(19) . . . . ?
N8 Ir N1 C6 2.56(18) . . . . ?
C6 N1 C2 C3 -0.4(4) . . . . ?
Ir N1 C2 C3 177.0(2) . . . . ?
N1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C2 N1 C6 C5 -0.5(4) . . . . ?
Ir N1 C6 C5 -178.1(2) . . . . ?
C2 N1 C6 C7 178.7(2) . . . . ?
Ir N1 C6 C7 1.1(3) . . . . ?
C4 C5 C6 N1 1.3(4) . . . . ?
C4 C5 C6 C7 -177.9(3) . . . . ?
N1 C6 C7 N8 -6.6(4) . . . . ?
C5 C6 C7 N8 172.6(3) . . . . ?
N1 C6 C7 C11 173.8(3) . . . . ?
C5 C6 C7 C11 -7.0(5) . . . . ?
C11 C7 N8 N9 0.6(3) . . . . ?
C6 C7 N8 N9 -179.1(2) . . . . ?
C11 C7 N8 Ir -171.4(2) . . . . ?
C6 C7 N8 Ir 8.8(3) . . . . ?
C52 Ir N8 N9 2.2(3) . . . . ?
C32 Ir N8 N9 172.9(8) . . . . ?
N21 Ir N8 N9 97.8(3) . . . . ?
N41 Ir N8 N9 -78.0(3) . . . . ?
N1 Ir N8 N9 -175.4(3) . . . . ?
C52 Ir N8 C7 171.6(2) . . . . ?
C32 Ir N8 C7 -17.8(10) . . . . ?
N21 Ir N8 C7 -92.9(2) . . . . ?
N41 Ir N8 C7 91.4(2) . . . . ?
N1 Ir N8 C7 -6.0(2) . . . . ?
C7 N8 N9 N10 -0.8(3) . . . . ?
Ir N8 N9 N10 169.0(2) . . . . ?
N8 N9 N10 C11 0.6(4) . . . . ?
N9 N10 C11 C7 -0.2(4) . . . . ?
N9 N10 C11 C12 -176.4(3) . . . . ?
N8 C7 C11 N10 -0.2(4) . . . . ?
C6 C7 C11 N10 179.5(3) . . . . ?
N8 C7 C11 C12 175.5(3) . . . . ?
C6 C7 C11 C12 -4.8(6) . . . . ?
N10 C11 C12 C13 83.0(5) . . . . ?
C7 C11 C12 C13 -92.2(5) . . . . ?
N10 C11 C12 C17 -101.9(4) . . . . ?
C7 C11 C12 C17 82.9(5) . . . . ?
C17 C12 C13 F13 -179.1(4) . . . . ?
C11 C12 C13 F13 -3.6(6) . . . . ?
C17 C12 C13 C14 0.8(7) . . . . ?
C11 C12 C13 C14 176.2(4) . . . . ?
F13 C13 C14 F14 0.8(8) . . . . ?
C12 C13 C14 F14 -179.0(5) . . . . ?
F13 C13 C14 C15 -179.8(5) . . . . ?
C12 C13 C14 C15 0.4(8) . . . . ?
F14 C14 C15 F15 0.6(8) . . . . ?
C13 C14 C15 F15 -178.8(4) . . . . ?
F14 C14 C15 C16 178.7(5) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
F15 C15 C16 F16 0.4(6) . . . . ?
C14 C15 C16 F16 -177.7(4) . . . . ?
F15 C15 C16 C17 177.9(4) . . . . ?
C14 C15 C16 C17 -0.2(6) . . . . ?
F16 C16 C17 F17 1.3(6) . . . . ?
C15 C16 C17 F17 -176.2(4) . . . . ?
F16 C16 C17 C12 179.0(3) . . . . ?
C15 C16 C17 C12 1.4(6) . . . . ?
C13 C12 C17 F17 175.9(4) . . . . ?
C11 C12 C17 F17 0.6(5) . . . . ?
C13 C12 C17 C16 -1.7(6) . . . . ?
C11 C12 C17 C16 -177.0(3) . . . . ?
C52 Ir N21 C22 91.3(2) . . . . ?
C32 Ir N21 C22 177.4(3) . . . . ?
N41 Ir N21 C22 137.5(6) . . . . ?
N8 Ir N21 C22 -9.5(2) . . . . ?
N1 Ir N21 C22 -85.4(2) . . . . ?
C52 Ir N21 C26 -85.7(2) . . . . ?
C32 Ir N21 C26 0.4(2) . . . . ?
N41 Ir N21 C26 -39.4(8) . . . . ?
N8 Ir N21 C26 173.5(2) . . . . ?
N1 Ir N21 C26 97.6(2) . . . . ?
C26 N21 C22 C23 0.8(4) . . . . ?
Ir N21 C22 C23 -176.1(2) . . . . ?
N21 C22 C23 C24 -0.6(5) . . . . ?
C22 C23 C24 C25 -0.1(6) . . . . ?
C23 C24 C25 C26 0.5(6) . . . . ?
C22 N21 C26 C25 -0.3(4) . . . . ?
Ir N21 C26 C25 176.8(2) . . . . ?
C22 N21 C26 C27 -178.7(3) . . . . ?
Ir N21 C26 C27 -1.7(3) . . . . ?
C24 C25 C26 N21 -0.3(5) . . . . ?
C24 C25 C26 C27 177.9(3) . . . . ?
N21 C26 C27 C28 -178.4(3) . . . . ?
C25 C26 C27 C28 3.4(5) . . . . ?
N21 C26 C27 C32 2.4(4) . . . . ?
C25 C26 C27 C32 -175.9(3) . . . . ?
C32 C27 C28 F28 -178.4(3) . . . . ?
C26 C27 C28 F28 2.4(5) . . . . ?
C32 C27 C28 C29 0.9(5) . . . . ?
C26 C27 C28 C29 -178.3(3) . . . . ?
F28 C28 C29 C30 179.6(3) . . . . ?
C27 C28 C29 C30 0.3(5) . . . . ?
C28 C29 C30 F30 179.1(3) . . . . ?
C28 C29 C30 C31 -1.0(6) . . . . ?
F30 C30 C31 C32 -179.7(3) . . . . ?
C29 C30 C31 C32 0.4(5) . . . . ?
C30 C31 C32 C27 0.9(5) . . . . ?
C30 C31 C32 Ir -179.3(2) . . . . ?
C28 C27 C32 C31 -1.5(4) . . . . ?
C26 C27 C32 C31 177.8(3) . . . . ?
C28 C27 C32 Ir 178.7(2) . . . . ?
C26 C27 C32 Ir -2.0(3) . . . . ?
C52 Ir C32 C31 -84.2(3) . . . . ?
N21 Ir C32 C31 -178.9(3) . . . . ?
N41 Ir C32 C31 -4.0(3) . . . . ?
N8 Ir C32 C31 104.9(9) . . . . ?
N1 Ir C32 C31 93.5(3) . . . . ?
C52 Ir C32 C27 95.6(2) . . . . ?
N21 Ir C32 C27 0.9(2) . . . . ?
N41 Ir C32 C27 175.8(2) . . . . ?
N8 Ir C32 C27 -75.2(9) . . . . ?
N1 Ir C32 C27 -86.7(2) . . . . ?
C52 Ir N41 C42 -179.2(3) . . . . ?
C32 Ir N41 C42 94.6(3) . . . . ?
N21 Ir N41 C42 133.9(6) . . . . ?
N8 Ir N41 C42 -78.7(3) . . . . ?
N1 Ir N41 C42 -2.8(3) . . . . ?
C52 Ir N41 C46 4.2(2) . . . . ?
C32 Ir N41 C46 -82.0(2) . . . . ?
N21 Ir N41 C46 -42.7(8) . . . . ?
N8 Ir N41 C46 104.7(2) . . . . ?
N1 Ir N41 C46 -179.4(2) . . . . ?
C46 N41 C42 C43 1.3(5) . . . . ?
Ir N41 C42 C43 -175.2(3) . . . . ?
N41 C42 C43 C44 -0.8(6) . . . . ?
C42 C43 C44 C45 0.4(6) . . . . ?
C43 C44 C45 C46 -0.5(5) . . . . ?
C42 N41 C46 C45 -1.3(4) . . . . ?
Ir N41 C46 C45 175.5(2) . . . . ?
C42 N41 C46 C47 179.1(3) . . . . ?
Ir N41 C46 C47 -4.1(3) . . . . ?
C44 C45 C46 N41 1.0(5) . . . . ?
C44 C45 C46 C47 -179.5(3) . . . . ?
N41 C46 C47 C48 -178.7(3) . . . . ?
C45 C46 C47 C48 1.8(5) . . . . ?
N41 C46 C47 C52 1.3(4) . . . . ?
C45 C46 C47 C52 -178.3(3) . . . . ?
C52 C47 C48 F48 -178.1(3) . . . . ?
C46 C47 C48 F48 1.8(5) . . . . ?
C52 C47 C48 C49 0.7(5) . . . . ?
C46 C47 C48 C49 -179.4(3) . . . . ?
F48 C48 C49 C50 178.3(3) . . . . ?
C47 C48 C49 C50 -0.5(5) . . . . ?
C48 C49 C50 F50 -179.8(3) . . . . ?
C48 C49 C50 C51 -0.2(5) . . . . ?
F50 C50 C51 C52 -179.6(3) . . . . ?
C49 C50 C51 C52 0.8(5) . . . . ?
C50 C51 C52 C47 -0.7(4) . . . . ?
C50 C51 C52 Ir 176.9(2) . . . . ?
C48 C47 C52 C51 -0.1(4) . . . . ?
C46 C47 C52 C51 180.0(3) . . . . ?
C48 C47 C52 Ir -177.9(2) . . . . ?
C46 C47 C52 Ir 2.2(3) . . . . ?
C32 Ir C52 C51 -87.1(3) . . . . ?
N21 Ir C52 C51 -6.7(3) . . . . ?
N41 Ir C52 C51 179.1(3) . . . . ?
N8 Ir C52 C51 91.8(3) . . . . ?
N1 Ir C52 C51 124.1(12) . . . . ?
C32 Ir C52 C47 90.5(2) . . . . ?
N21 Ir C52 C47 170.9(2) . . . . ?
N41 Ir C52 C47 -3.3(2) . . . . ?
N8 Ir C52 C47 -90.6(2) . . . . ?
N1 Ir C52 C47 -58.3(14) . . . . ?
C65 O61 C62 C63 14.8(7) . . . . ?
O61 C62 C63 C64 -8.7(9) . . . . ?
C62 C63 C64 C65 -0.2(9) . . . . ?
C62 O61 C65 C64 -14.5(7) . . . . ?
C63 C64 C65 O61 8.8(8) . . . . ?
