#------------------------------------------------------------------------------
#$Date: 2019-10-18 10:38:11 +0300 (Fri, 18 Oct 2019) $
#$Revision: 219417 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/47/7234710.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_7234710
loop_
_publ_author_name
'Adam F. Henwood'
'Ashu K. Bansal'
'David B. Cordes'
'Alexandra M. Z. Slawin'
'Ifor D. W. Samuel'
'Eli Zysman-Colman'
_publ_section_title
;
 Solubilised bright blue-emitting iridium complexes for solution processed
 OLEDs
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3726
_journal_page_last               3737
_journal_paper_doi               10.1039/C6TC00151C
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C54 H44 F4 Ir N6, F6 P, C4 H10 O'
_chemical_formula_sum            'C58 H54 F10 Ir N6 O P'
_chemical_formula_weight         1264.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 125.688(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   45.7191(10)
_cell_length_b                   9.4584(17)
_cell_length_c                   33.211(7)
_cell_measurement_reflns_used    11725
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      1.80
_cell_volume                     11664(3)
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            44211
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         1.097
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.398
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             5072.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile/diethyl ether'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         5.73
_refine_diff_density_min         -2.43
_refine_ls_extinction_coef       0.00167(15)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     703
_refine_ls_number_reflns         10577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1792P)²+43.1065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2938
_reflns_number_gt                8481
_reflns_number_total             10577
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            J-Mater-Chem-C-2016-4-3726.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7234710
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'
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 0.66652(2) 0.76744(4) 0.52855(2) 0.0330(2) Uani 1 1 d . . . . .
P1 P 0.50932(9) 0.0286(4) 0.41017(12) 0.0640(8) Uani 1 1 d . . . . .
F1 F 0.5477(2) 0.1075(11) 0.4436(3) 0.091(3) Uani 1 1 d . . . . .
F2 F 0.5113(2) 0.0398(9) 0.3645(3) 0.088(2) Uani 1 1 d . . . . .
F3 F 0.4899(2) 0.1809(11) 0.3962(3) 0.084(2) Uani 1 1 d . . . . .
F4 F 0.5080(2) 0.0157(8) 0.4571(3) 0.0752(19) Uani 1 1 d . . . . .
F5 F 0.4726(3) -0.0494(11) 0.3779(3) 0.110(3) Uani 1 1 d . . . . .
F6 F 0.5308(3) -0.1172(9) 0.4251(3) 0.092(3) Uani 1 1 d . . . . .
F10 F 0.7297(2) 1.2833(6) 0.5663(3) 0.0582(17) Uani 1 1 d . . . . .
F12 F 0.79248(14) 0.9318(6) 0.68627(19) 0.0480(13) Uani 1 1 d . . . . .
F31 F 0.76449(15) 0.4541(6) 0.5259(2) 0.0481(13) Uani 1 1 d . . . . .
F33 F 0.6914(2) 0.7560(6) 0.3920(2) 0.0510(16) Uani 1 1 d . . . . .
O61 O 0.3571(5) 0.7777(13) 0.2849(5) 0.107(4) Uani 1 1 d . . . . .
N1 N 0.70038(19) 0.6671(8) 0.5951(2) 0.0334(15) Uani 1 1 d . . . . .
N22 N 0.6413(2) 0.8756(8) 0.4632(3) 0.0400(17) Uani 1 1 d . . . . .
N43 N 0.6287(2) 0.8240(9) 0.5443(3) 0.0419(17) Uani 1 1 d . . . . .
N45 N 0.5766(2) 0.7876(9) 0.5347(3) 0.0402(18) Uani 1 1 d . . . . .
N49 N 0.6267(2) 0.6050(9) 0.4936(3) 0.0408(17) Uani 1 1 d . . . . .
N52 N 0.5741(2) 0.5136(10) 0.4697(3) 0.049(2) Uani 1 1 d . . . . .
C2 C 0.7328(3) 0.7320(9) 0.6282(4) 0.033(2) Uani 1 1 d . . . . .
C3 C 0.7596(2) 0.6605(10) 0.6704(3) 0.0371(19) Uani 1 1 d . . . . .
H3 H 0.7820 0.7059 0.6932 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7543(2) 0.5226(10) 0.6800(3) 0.0375(19) Uani 1 1 d . . . . .
C5 C 0.7206(2) 0.4605(10) 0.6458(3) 0.0382(19) Uani 1 1 d . . . . .
H5 H 0.7159 0.3673 0.6513 0.046 Uiso 1 1 calc R U . . .
C6 C 0.6942(2) 0.5339(9) 0.6040(3) 0.0376(19) Uani 1 1 d . . . . .
H6 H 0.6714 0.4908 0.5812 0.045 Uiso 1 1 calc R U . . .
C7 C 0.7340(2) 0.8760(10) 0.6136(3) 0.0361(18) Uani 1 1 d . . . . .
C8 C 0.7033(2) 0.9193(10) 0.5665(3) 0.038(2) Uani 1 1 d . . . . .
C9 C 0.7017(3) 1.0589(10) 0.5508(3) 0.041(2) Uani 1 1 d . . . . .
H9 H 0.6814 1.0917 0.5198 0.049 Uiso 1 1 calc R U . . .
C10 C 0.7306(3) 1.1465(10) 0.5818(4) 0.047(2) Uani 1 1 d . . . . .
C11 C 0.7609(3) 1.1090(10) 0.6272(4) 0.044(2) Uani 1 1 d . . . . .
H11 H 0.7800 1.1736 0.6474 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7618(2) 0.9714(10) 0.6417(3) 0.0396(19) Uani 1 1 d . . . . .
C13 C 0.7831(2) 0.4338(10) 0.7217(3) 0.041(2) Uani 1 1 d . . . . .
C14 C 0.8111(3) 0.3844(10) 0.7207(3) 0.045(2) Uani 1 1 d . . . . .
C15 C 0.8363(3) 0.2893(11) 0.7576(4) 0.044(2) Uani 1 1 d . . . . .
H15 H 0.8550 0.2511 0.7565 0.052 Uiso 1 1 calc R U . . .
C16 C 0.8334(3) 0.2517(10) 0.7961(4) 0.047(3) Uani 1 1 d . . . . .
C17 C 0.8057(3) 0.3061(12) 0.7965(4) 0.047(2) Uani 1 1 d . . . . .
H17 H 0.8039 0.2798 0.8226 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7803(3) 0.3978(12) 0.7604(4) 0.048(2) Uani 1 1 d . . . . .
C19 C 0.8162(3) 0.4310(12) 0.6812(3) 0.047(2) Uani 1 1 d . . . . .
H19A H 0.8248 0.5288 0.6875 0.056 Uiso 1 1 calc R U . . .
H19B H 0.7931 0.4246 0.6484 0.056 Uiso 1 1 calc R U . . .
H19C H 0.8338 0.3693 0.6822 0.056 Uiso 1 1 calc R U . . .
C20 C 0.8602(3) 0.1457(14) 0.8356(4) 0.064(3) Uani 1 1 d . . . . .
H20A H 0.8585 0.0560 0.8196 0.076 Uiso 1 1 calc R U . . .
H20B H 0.8545 0.1300 0.8594 0.076 Uiso 1 1 calc R U . . .
H20C H 0.8847 0.1834 0.8528 0.076 Uiso 1 1 calc R U . . .
C21 C 0.7514(3) 0.4625(14) 0.7636(4) 0.065(3) Uani 1 1 d . . . . .
H21A H 0.7588 0.4567 0.7978 0.078 Uiso 1 1 calc R U . . .
H21B H 0.7288 0.4108 0.7417 0.078 Uiso 1 1 calc R U . . .
H21C H 0.7480 0.5618 0.7533 0.078 Uiso 1 1 calc R U . . .
C23 C 0.6559(2) 0.8592(11) 0.4367(3) 0.042(2) Uani 1 1 d . . . . .
C24 C 0.6443(3) 0.9463(12) 0.3959(3) 0.048(2) Uani 1 1 d . . . . .
H24 H 0.6554 0.9393 0.3791 0.058 Uiso 1 1 calc R U . . .
C25 C 0.6169(3) 1.0425(13) 0.3800(4) 0.056(3) Uani 1 1 d . . . . .
C26 C 0.6001(3) 1.0498(12) 0.4048(4) 0.052(2) Uani 1 1 d . . . . .
H26 H 0.5803 1.1114 0.3936 0.063 Uiso 1 1 calc R U . . .
C27 C 0.6132(3) 0.9658(12) 0.4451(4) 0.050(2) Uani 1 1 d . . . . .
H27 H 0.6019 0.9705 0.4617 0.060 Uiso 1 1 calc R U . . .
C28 C 0.6844(3) 0.7521(9) 0.4578(4) 0.034(2) Uani 1 1 d . . . . .
C29 C 0.6952(2) 0.6953(10) 0.5040(3) 0.0341(18) Uani 1 1 d . . . . .
C30 C 0.7223(2) 0.5950(9) 0.5269(3) 0.0359(18) Uani 1 1 d . . . . .
H30 H 0.7303 0.5573 0.5583 0.043 Uiso 1 1 calc R U . . .
C31 C 0.7377(3) 0.5499(9) 0.5031(3) 0.039(2) Uani 1 1 d . . . . .
C32 C 0.7279(3) 0.6023(10) 0.4589(3) 0.043(2) Uani 1 1 d . . . . .
H32 H 0.7391 0.5709 0.4437 0.052 Uiso 1 1 calc R U . . .
C33 C 0.7012(3) 0.7025(11) 0.4367(3) 0.039(2) Uani 1 1 d . . . . .
C34 C 0.6050(4) 1.1404(16) 0.3372(4) 0.068(3) Uani 1 1 d . . . . .
C35 C 0.6233(5) 1.2574(14) 0.3434(6) 0.072(4) Uani 1 1 d . . . . .
C36 C 0.6123(4) 1.3415(16) 0.3000(6) 0.084(4) Uani 1 1 d . . . . .
H36 H 0.6258 1.4227 0.3032 0.101 Uiso 1 1 calc R U . . .
C37 C 0.5826(5) 1.303(2) 0.2548(5) 0.088(5) Uani 1 1 d . . . . .
C38 C 0.5646(6) 1.180(3) 0.2474(6) 0.116(7) Uani 1 1 d . . . . .
H38 H 0.5457 1.1512 0.2148 0.139 Uiso 1 1 calc R U . . .
C39 C 0.5742(4) 1.0972(19) 0.2885(5) 0.094(5) Uani 1 1 d . . . . .
C40 C 0.6561(6) 1.2954(16) 0.3938(8) 0.104(7) Uani 1 1 d . . . . .
H40A H 0.6775 1.2536 0.3983 0.125 Uiso 1 1 calc R U . . .
H40B H 0.6536 1.2588 0.4192 0.125 Uiso 1 1 calc R U . . .
H40C H 0.6587 1.3984 0.3967 0.125 Uiso 1 1 calc R U . . .
C41 C 0.5680(8) 1.389(2) 0.2078(7) 0.172(12) Uani 1 1 d . . . . .
H41A H 0.5504 1.4582 0.2036 0.206 Uiso 1 1 calc R U . . .
H41B H 0.5564 1.3259 0.1791 0.206 Uiso 1 1 calc R U . . .
H41C H 0.5879 1.4392 0.2106 0.206 Uiso 1 1 calc R U . . .
C42 C 0.5513(7) 0.967(3) 0.2813(6) 0.186(14) Uani 1 1 d . . . . .
H42A H 0.5407 0.9263 0.2484 0.224 Uiso 1 1 calc R U . . .
H42B H 0.5321 0.9954 0.2844 0.224 Uiso 1 1 calc R U . . .
H42C H 0.5666 0.8961 0.3067 0.224 Uiso 1 1 calc R U . . .
C44 C 0.5985(3) 0.7425(9) 0.5232(4) 0.036(2) Uani 1 1 d . . . . .
C46 C 0.5934(3) 0.9092(11) 0.5652(4) 0.047(2) Uani 1 1 d . . . . .
H46 H 0.5848 0.9655 0.5799 0.056 Uiso 1 1 calc R U . . .
C47 C 0.6247(3) 0.9286(10) 0.5688(4) 0.045(2) Uani 1 1 d . . . . .
H47 H 0.6412 1.0043 0.5860 0.054 Uiso 1 1 calc R U . . .
C48 C 0.5982(2) 0.6207(10) 0.4955(3) 0.0390(19) Uani 1 1 d . . . . .
C50 C 0.6207(3) 0.4868(13) 0.4662(4) 0.058(3) Uani 1 1 d . . . . .
H50 H 0.6362 0.4512 0.4583 0.070 Uiso 1 1 calc R U . . .
C51 C 0.5886(3) 0.4277(12) 0.4521(4) 0.056(3) Uani 1 1 d . . . . .
H51 H 0.5783 0.3431 0.4336 0.067 Uiso 1 1 calc R U . . .
C53 C 0.5422(3) 0.7313(10) 0.5214(4) 0.042(2) Uani 1 1 d . . . . .
H53A H 0.5244 0.7372 0.4849 0.051 Uiso 1 1 calc R U . . .
H53B H 0.5334 0.7908 0.5368 0.051 Uiso 1 1 calc R U . . .
C54 C 0.5447(2) 0.5802(11) 0.5374(3) 0.043(2) Uani 1 1 d . . . . .
C55 C 0.5438(2) 0.4663(11) 0.5101(3) 0.046(2) Uani 1 1 d . . . . .
C56 C 0.5462(3) 0.3271(12) 0.5267(4) 0.056(3) Uani 1 1 d . . . . .
H56 H 0.5450 0.2494 0.5077 0.067 Uiso 1 1 calc R U . . .
C57 C 0.5501(3) 0.3038(13) 0.5706(4) 0.052(2) Uani 1 1 d . . . . .
H57 H 0.5518 0.2099 0.5819 0.062 Uiso 1 1 calc R U . . .
C58 C 0.5515(3) 0.4170(12) 0.5983(4) 0.050(2) Uani 1 1 d . . . . .
H58 H 0.5551 0.4001 0.6291 0.060 Uiso 1 1 calc R U . . .
C59 C 0.5479(2) 0.5538(11) 0.5816(4) 0.043(2) Uani 1 1 d . . . . .
H59 H 0.5476 0.6302 0.5999 0.052 Uiso 1 1 calc R U . . .
C60 C 0.5389(3) 0.4912(13) 0.4605(4) 0.053(3) Uani 1 1 d . . . . .
H60A H 0.5269 0.4083 0.4386 0.064 Uiso 1 1 calc R U . . .
H60B H 0.5235 0.5751 0.4436 0.064 Uiso 1 1 calc R U . . .
C61 C 0.3577(4) 0.8416(18) 0.3237(6) 0.104(6) Uani 1 1 d . . . . .
H61A H 0.3814 0.8275 0.3558 0.125 Uiso 1 1 calc R U . . .
H61B H 0.3529 0.9443 0.3178 0.125 Uiso 1 1 calc R U . . .
C62 C 0.3313(7) 0.776(2) 0.3234(9) 0.131(10) Uani 1 1 d . . . . .
H62A H 0.3253 0.6860 0.3056 0.157 Uiso 1 1 calc R U . . .
H62B H 0.3098 0.8363 0.3069 0.157 Uiso 1 1 calc R U . . .
H62C H 0.3395 0.7581 0.3576 0.157 Uiso 1 1 calc R U . . .
C63 C 0.3834(5) 0.831(3) 0.2806(7) 0.115(7) Uani 1 1 d . . . . .
H63A H 0.4075 0.8180 0.3121 0.138 Uiso 1 1 calc R U . . .
H63B H 0.3795 0.9333 0.2729 0.138 Uiso 1 1 calc R U . . .
C64 C 0.3809(10) 0.750(4) 0.2383(16) 0.25(2) Uani 1 1 d . . . . .
H64A H 0.3558 0.7477 0.2090 0.298 Uiso 1 1 calc R U . . .
H64B H 0.3896 0.6530 0.2491 0.298 Uiso 1 1 calc R U . . .
H64C H 0.3958 0.7976 0.2300 0.298 Uiso 1 1 calc R U . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ir Ir -1.4442 7.9887
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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
C8 Ir1 C29 89.6(3) . .
C8 Ir1 N22 93.2(3) . .
C29 Ir1 N22 80.6(3) . .
C8 Ir1 N1 79.9(3) . .
C29 Ir1 N1 91.1(3) . .
N22 Ir1 N1 169.3(3) . .
C8 Ir1 N49 174.6(3) . .
C29 Ir1 N49 94.9(3) . .
N22 Ir1 N49 90.5(3) . .
N1 Ir1 N49 97.0(3) . .
C8 Ir1 N43 99.6(3) . .
C29 Ir1 N43 170.3(3) . .
N22 Ir1 N43 95.7(3) . .
N1 Ir1 N43 93.5(3) . .
N49 Ir1 N43 76.1(3) . .
F5 P1 F2 90.9(5) . .
F5 P1 F6 91.5(6) . .
F2 P1 F6 89.2(4) . .
F5 P1 F4 89.7(5) . .
F2 P1 F4 178.9(5) . .
F6 P1 F4 89.9(4) . .
F5 P1 F1 179.3(6) . .
F2 P1 F1 88.9(5) . .
F6 P1 F1 87.7(5) . .
F4 P1 F1 90.5(4) . .
F5 P1 F3 91.9(6) . .
F2 P1 F3 89.6(4) . .
F6 P1 F3 176.4(6) . .
F4 P1 F3 91.3(4) . .
F1 P1 F3 88.8(5) . .
C63 O61 C61 112.5(16) . .
C6 N1 C2 120.4(8) . .
C6 N1 Ir1 122.8(6) . .
C2 N1 Ir1 116.1(6) . .
C27 N22 C23 118.1(8) . .
C27 N22 Ir1 126.0(6) . .
C23 N22 Ir1 115.8(6) . .
C47 N43 C44 105.5(7) . .
C47 N43 Ir1 137.4(7) . .
C44 N43 Ir1 117.0(6) . .
C44 N45 C46 106.0(8) . .
C44 N45 C53 130.6(8) . .
C46 N45 C53 123.4(8) . .
C48 N49 C50 107.3(8) . .
C48 N49 Ir1 115.8(6) . .
C50 N49 Ir1 136.8(6) . .
C48 N52 C51 107.0(8) . .
C48 N52 C60 128.4(8) . .
C51 N52 C60 124.6(8) . .
N1 C2 C3 119.7(8) . .
N1 C2 C7 112.5(8) . .
C3 C2 C7 127.7(9) . .
C2 C3 C4 121.2(8) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C3 C4 C5 117.5(8) . .
C3 C4 C13 124.0(8) . .
C5 C4 C13 118.3(8) . .
C6 C5 C4 120.4(8) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
N1 C6 C5 120.8(8) . .
N1 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C12 C7 C8 118.8(8) . .
C12 C7 C2 125.6(8) . .
C8 C7 C2 115.6(8) . .
C9 C8 C7 118.9(9) . .
C9 C8 Ir1 126.7(7) . .
C7 C8 Ir1 114.4(7) . .
C10 C9 C8 117.9(9) . .
C10 C9 H9 121.0 . .
C8 C9 H9 121.0 . .
C11 C10 C9 125.2(9) . .
C11 C10 F10 116.3(9) . .
C9 C10 F10 118.4(9) . .
C10 C11 C12 115.7(9) . .
C10 C11 H11 122.1 . .
C12 C11 H11 122.1 . .
F12 C12 C11 116.0(8) . .
F12 C12 C7 120.6(8) . .
C11 C12 C7 123.4(9) . .
C14 C13 C18 121.4(9) . .
C14 C13 C4 119.8(8) . .
C18 C13 C4 118.8(8) . .
C13 C14 C15 119.4(9) . .
C13 C14 C19 122.1(9) . .
C15 C14 C19 118.5(9) . .
C16 C15 C14 119.4(10) . .
C16 C15 H15 120.3 . .
C14 C15 H15 120.3 . .
C17 C16 C15 119.4(10) . .
C17 C16 C20 121.2(10) . .
C15 C16 C20 119.4(11) . .
C16 C17 C18 122.5(9) . .
C16 C17 H17 118.7 . .
C18 C17 H17 118.7 . .
C17 C18 C13 117.8(9) . .
C17 C18 C21 121.1(9) . .
C13 C18 C21 121.0(9) . .
C14 C19 H19A 109.5 . .
C14 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C14 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C16 C20 H20A 109.5 . .
C16 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C16 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
N22 C23 C24 119.8(9) . .
N22 C23 C28 113.4(8) . .
C24 C23 C28 126.7(8) . .
C25 C24 C23 120.4(8) . .
C25 C24 H24 119.8 . .
C23 C24 H24 119.8 . .
C24 C25 C26 119.2(9) . .
C24 C25 C34 120.8(10) . .
C26 C25 C34 120.0(10) . .
C27 C26 C25 117.8(10) . .
C27 C26 H26 121.1 . .
C25 C26 H26 121.1 . .
N22 C27 C26 124.3(9) . .
N22 C27 H27 117.8 . .
C26 C27 H27 117.8 . .
C33 C28 C29 118.2(9) . .
C33 C28 C23 126.4(9) . .
C29 C28 C23 115.4(8) . .
C30 C29 C28 119.3(8) . .
C30 C29 Ir1 126.3(6) . .
C28 C29 Ir1 114.3(7) . .
C29 C30 C31 118.9(8) . .
C29 C30 H30 120.6 . .
C31 C30 H30 120.6 . .
F31 C31 C32 118.3(7) . .
F31 C31 C30 118.7(8) . .
C32 C31 C30 123.0(9) . .
C31 C32 C33 117.4(8) . .
C31 C32 H32 121.3 . .
C33 C32 H32 121.3 . .
C32 C33 F33 117.3(8) . .
C32 C33 C28 123.1(8) . .
F33 C33 C28 119.6(9) . .
C35 C34 C39 121.4(13) . .
C35 C34 C25 121.2(13) . .
C39 C34 C25 117.3(13) . .
C34 C35 C36 118.7(16) . .
C34 C35 C40 120.1(13) . .
C36 C35 C40 121.1(15) . .
C37 C36 C35 119.5(16) . .
C37 C36 H36 120.2 . .
C35 C36 H36 120.2 . .
C38 C37 C36 122.4(15) . .
C38 C37 C41 114.5(17) . .
C36 C37 C41 123.0(19) . .
C37 C38 C39 119.3(15) . .
C37 C38 H38 120.4 . .
C39 C38 H38 120.4 . .
C38 C39 C34 118.4(16) . .
C38 C39 C42 119.9(15) . .
C34 C39 C42 121.7(12) . .
C35 C40 H40A 109.5 . .
C35 C40 H40B 109.5 . .
H40A C40 H40B 109.5 . .
C35 C40 H40C 109.5 . .
H40A C40 H40C 109.5 . .
H40B C40 H40C 109.5 . .
C37 C41 H41A 109.5 . .
C37 C41 H41B 109.5 . .
H41A C41 H41B 109.5 . .
C37 C41 H41C 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
C39 C42 H42A 109.5 . .
C39 C42 H42B 109.5 . .
H42A C42 H42B 109.5 . .
C39 C42 H42C 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
N45 C44 N43 112.2(8) . .
N45 C44 C48 134.1(9) . .
N43 C44 C48 113.5(8) . .
C47 C46 N45 105.9(8) . .
C47 C46 H46 127.0 . .
N45 C46 H46 127.0 . .
N43 C47 C46 110.3(9) . .
N43 C47 H47 124.9 . .
C46 C47 H47 124.8 . .
N49 C48 N52 109.5(8) . .
N49 C48 C44 117.4(8) . .
N52 C48 C44 133.1(8) . .
N49 C50 C51 108.8(9) . .
N49 C50 H50 125.6 . .
C51 C50 H50 125.6 . .
C50 C51 N52 107.4(9) . .
C50 C51 H51 126.3 . .
N52 C51 H51 126.3 . .
N45 C53 C54 113.2(8) . .
N45 C53 H53A 108.9 . .
C54 C53 H53A 108.9 . .
N45 C53 H53B 108.9 . .
C54 C53 H53B 108.9 . .
H53A C53 H53B 107.8 . .
C55 C54 C59 119.2(10) . .
C55 C54 C53 122.3(9) . .
C59 C54 C53 118.6(9) . .
C54 C55 C56 120.1(9) . .
C54 C55 C60 120.5(10) . .
C56 C55 C60 119.4(10) . .
C57 C56 C55 119.8(10) . .
C57 C56 H56 120.1 . .
C55 C56 H56 120.1 . .
C56 C57 C58 120.3(11) . .
C56 C57 H57 119.9 . .
C58 C57 H57 119.9 . .
C59 C58 C57 120.7(10) . .
C59 C58 H58 119.7 . .
C57 C58 H58 119.7 . .
C58 C59 C54 119.9(9) . .
C58 C59 H59 120.0 . .
C54 C59 H59 120.0 . .
N52 C60 C55 109.8(8) . .
N52 C60 H60A 109.7 . .
C55 C60 H60A 109.7 . .
N52 C60 H60B 109.7 . .
C55 C60 H60B 109.7 . .
H60A C60 H60B 108.2 . .
C62 C61 O61 104.8(16) . .
C62 C61 H61A 110.8 . .
O61 C61 H61A 110.8 . .
C62 C61 H61B 110.8 . .
O61 C61 H61B 110.8 . .
H61A C61 H61B 108.9 . .
C61 C62 H62A 109.5 . .
C61 C62 H62B 109.5 . .
H62A C62 H62B 109.5 . .
C61 C62 H62C 109.5 . .
H62A C62 H62C 109.5 . .
H62B C62 H62C 109.5 . .
O61 C63 C64 108(2) . .
O61 C63 H63A 110.1 . .
C64 C63 H63A 110.1 . .
O61 C63 H63B 110.1 . .
C64 C63 H63B 110.1 . .
H63A C63 H63B 108.5 . .
C63 C64 H64A 109.5 . .
C63 C64 H64B 109.5 . .
H64A C64 H64B 109.5 . .
C63 C64 H64C 109.5 . .
H64A C64 H64C 109.5 . .
H64B C64 H64C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 C8 2.001(10) .
Ir1 C29 2.025(8) .
Ir1 N22 2.041(7) .
Ir1 N1 2.048(7) .
Ir1 N49 2.135(8) .
Ir1 N43 2.145(7) .
P1 F5 1.554(9) .
P1 F2 1.575(8) .
P1 F6 1.595(8) .
P1 F4 1.597(7) .
P1 F1 1.611(9) .
P1 F3 1.612(9) .
F10 C10 1.384(11) .
F12 C12 1.370(10) .
F31 C31 1.346(10) .
F33 C33 1.375(11) .
O61 C63 1.39(3) .
O61 C61 1.41(2) .
N1 C6 1.360(11) .
N1 C2 1.373(12) .
N22 C27 1.356(12) .
N22 C23 1.389(11) .
N43 C47 1.360(12) .
N43 C44 1.366(12) .
N45 C44 1.332(12) .
N45 C46 1.425(13) .
N45 C53 1.461(13) .
N49 C48 1.352(11) .
N49 C50 1.363(12) .
N52 C48 1.368(12) .
N52 C51 1.377(12) .
N52 C60 1.466(13) .
C2 C3 1.384(13) .
C2 C7 1.457(12) .
C3 C4 1.397(13) .
C3 H3 0.9500 .
C4 C5 1.402(12) .
C4 C13 1.494(13) .
C5 C6 1.382(12) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C12 1.386(12) .
C7 C8 1.422(13) .
C8 C9 1.406(12) .
C9 C10 1.380(14) .
C9 H9 0.9500 .
C10 C11 1.372(15) .
C11 C12 1.379(13) .
C11 H11 0.9500 .
C13 C14 1.382(14) .
C13 C18 1.407(12) .
C14 C15 1.411(14) .
C14 C19 1.523(13) .
C15 C16 1.406(15) .
C15 H15 0.9500 .
C16 C17 1.375(16) .
C16 C20 1.533(15) .
C17 C18 1.384(14) .
C17 H17 0.9500 .
C18 C21 1.513(15) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C23 C24 1.399(13) .
C23 C28 1.466(13) .
C24 C25 1.382(15) .
C24 H24 0.9500 .
C25 C26 1.419(14) .
C25 C34 1.507(15) .
C26 C27 1.358(14) .
C26 H26 0.9500 .
C27 H27 0.9500 .
C28 C33 1.383(14) .
C28 C29 1.417(13) .
C29 C30 1.383(13) .
C30 C31 1.397(11) .
C30 H30 0.9500 .
C31 C32 1.354(12) .
C32 C33 1.373(14) .
C32 H32 0.9500 .
C34 C35 1.33(2) .
C34 C39 1.45(2) .
C35 C36 1.454(19) .
C35 C40 1.50(3) .
C36 C37 1.36(2) .
C36 H36 0.9500 .
C37 C38 1.36(3) .
C37 C41 1.53(2) .
C38 C39 1.41(2) .
C38 H38 0.9500 .
C39 C42 1.54(2) .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C40 H40C 0.9800 .
C41 H41A 0.9800 .
C41 H41B 0.9800 .
C41 H41C 0.9800 .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
C44 C48 1.469(13) .
C46 C47 1.375(13) .
C46 H46 0.9500 .
C47 H47 0.9500 .
C50 C51 1.370(14) .
C50 H50 0.9500 .
C51 H51 0.9500 .
C53 C54 1.507(14) .
C53 H53A 0.9900 .
C53 H53B 0.9900 .
C54 C55 1.395(14) .
C54 C59 1.408(13) .
C55 C56 1.407(15) .
C55 C60 1.546(14) .
C56 C57 1.379(16) .
C56 H56 0.9500 .
C57 C58 1.388(15) .
C57 H57 0.9500 .
C58 C59 1.379(14) .
C58 H58 0.9500 .
C59 H59 0.9500 .
C60 H60A 0.9900 .
C60 H60B 0.9900 .
C61 C62 1.35(3) .
C61 H61A 0.9900 .
C61 H61B 0.9900 .
C62 H62A 0.9800 .
C62 H62B 0.9800 .
C62 H62C 0.9800 .
C63 C64 1.55(4) .
C63 H63A 0.9900 .
C63 H63B 0.9900 .
C64 H64A 0.9800 .
C64 H64B 0.9800 .
C64 H64C 0.9800 .
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
C6 N1 C2 C3 1.1(12) . . . .
Ir1 N1 C2 C3 -169.1(6) . . . .
C6 N1 C2 C7 -177.5(7) . . . .
Ir1 N1 C2 C7 12.3(9) . . . .
N1 C2 C3 C4 0.1(13) . . . .
C7 C2 C3 C4 178.5(8) . . . .
C2 C3 C4 C5 -1.1(12) . . . .
C2 C3 C4 C13 173.2(8) . . . .
C3 C4 C5 C6 0.9(12) . . . .
C13 C4 C5 C6 -173.8(8) . . . .
C2 N1 C6 C5 -1.3(12) . . . .
Ir1 N1 C6 C5 168.2(6) . . . .
C4 C5 C6 N1 0.3(13) . . . .
N1 C2 C7 C12 174.0(8) . . . .
C3 C2 C7 C12 -4.5(15) . . . .
N1 C2 C7 C8 -5.5(11) . . . .
C3 C2 C7 C8 176.0(8) . . . .
C12 C7 C8 C9 -2.2(11) . . . .
C2 C7 C8 C9 177.4(7) . . . .
C12 C7 C8 Ir1 176.6(6) . . . .
C2 C7 C8 Ir1 -3.9(9) . . . .
C7 C8 C9 C10 1.1(12) . . . .
Ir1 C8 C9 C10 -177.5(6) . . . .
C8 C9 C10 C11 -0.4(14) . . . .
C8 C9 C10 F10 178.8(7) . . . .
C9 C10 C11 C12 0.8(14) . . . .
F10 C10 C11 C12 -178.5(8) . . . .
C10 C11 C12 F12 178.0(8) . . . .
C10 C11 C12 C7 -1.9(13) . . . .
C8 C7 C12 F12 -177.2(7) . . . .
C2 C7 C12 F12 3.3(13) . . . .
C8 C7 C12 C11 2.6(13) . . . .
C2 C7 C12 C11 -176.9(8) . . . .
C3 C4 C13 C14 -69.2(12) . . . .
C5 C4 C13 C14 105.1(10) . . . .
C3 C4 C13 C18 113.3(10) . . . .
C5 C4 C13 C18 -72.4(11) . . . .
C18 C13 C14 C15 3.7(14) . . . .
C4 C13 C14 C15 -173.7(8) . . . .
C18 C13 C14 C19 -175.4(9) . . . .
C4 C13 C14 C19 7.1(13) . . . .
C13 C14 C15 C16 -3.0(14) . . . .
C19 C14 C15 C16 176.2(9) . . . .
C14 C15 C16 C17 1.3(15) . . . .
C14 C15 C16 C20 178.6(10) . . . .
C15 C16 C17 C18 -0.2(17) . . . .
C20 C16 C17 C18 -177.5(11) . . . .
C16 C17 C18 C13 0.8(16) . . . .
C16 C17 C18 C21 -176.4(11) . . . .
C14 C13 C18 C17 -2.6(15) . . . .
C4 C13 C18 C17 174.8(9) . . . .
C14 C13 C18 C21 174.6(10) . . . .
C4 C13 C18 C21 -7.9(15) . . . .
C27 N22 C23 C24 7.3(14) . . . .
Ir1 N22 C23 C24 -169.5(7) . . . .
C27 N22 C23 C28 -176.0(8) . . . .
Ir1 N22 C23 C28 7.2(10) . . . .
N22 C23 C24 C25 -4.1(15) . . . .
C28 C23 C24 C25 179.7(10) . . . .
C23 C24 C25 C26 -1.3(17) . . . .
C23 C24 C25 C34 177.9(11) . . . .
C24 C25 C26 C27 3.2(17) . . . .
C34 C25 C26 C27 -175.9(11) . . . .
C23 N22 C27 C26 -5.4(16) . . . .
Ir1 N22 C27 C26 171.1(8) . . . .
C25 C26 C27 N22 0.1(17) . . . .
N22 C23 C28 C33 172.7(9) . . . .
C24 C23 C28 C33 -10.8(16) . . . .
N22 C23 C28 C29 -6.9(12) . . . .
C24 C23 C28 C29 169.6(9) . . . .
C33 C28 C29 C30 1.1(13) . . . .
C23 C28 C29 C30 -179.2(8) . . . .
C33 C28 C29 Ir1 -176.2(7) . . . .
C23 C28 C29 Ir1 3.4(10) . . . .
C28 C29 C30 C31 -1.5(13) . . . .
Ir1 C29 C30 C31 175.5(7) . . . .
C29 C30 C31 F31 178.8(8) . . . .
C29 C30 C31 C32 1.5(14) . . . .
F31 C31 C32 C33 -178.4(8) . . . .
C30 C31 C32 C33 -1.1(14) . . . .
C31 C32 C33 F33 179.7(8) . . . .
C31 C32 C33 C28 0.7(14) . . . .
C29 C28 C33 C32 -0.8(14) . . . .
C23 C28 C33 C32 179.6(9) . . . .
C29 C28 C33 F33 -179.7(8) . . . .
C23 C28 C33 F33 0.7(14) . . . .
C24 C25 C34 C35 -80.2(17) . . . .
C26 C25 C34 C35 99.0(15) . . . .
C24 C25 C34 C39 96.1(15) . . . .
C26 C25 C34 C39 -84.8(16) . . . .
C39 C34 C35 C36 -1(2) . . . .
C25 C34 C35 C36 175.0(12) . . . .
C39 C34 C35 C40 -177.0(14) . . . .
C25 C34 C35 C40 -1(2) . . . .
C34 C35 C36 C37 4(2) . . . .
C40 C35 C36 C37 179.4(15) . . . .
C35 C36 C37 C38 -7(3) . . . .
C35 C36 C37 C41 176.8(17) . . . .
C36 C37 C38 C39 8(4) . . . .
C41 C37 C38 C39 -176(2) . . . .
C37 C38 C39 C34 -5(3) . . . .
C37 C38 C39 C42 173(2) . . . .
C35 C34 C39 C38 2(3) . . . .
C25 C34 C39 C38 -174.6(16) . . . .
C35 C34 C39 C42 -176(2) . . . .
C25 C34 C39 C42 8(3) . . . .
C46 N45 C44 N43 0.8(11) . . . .
C53 N45 C44 N43 -178.6(9) . . . .
C46 N45 C44 C48 176.6(10) . . . .
C53 N45 C44 C48 -2.9(19) . . . .
C47 N43 C44 N45 -2.2(11) . . . .
Ir1 N43 C44 N45 -179.1(6) . . . .
C47 N43 C44 C48 -178.9(8) . . . .
Ir1 N43 C44 C48 4.2(11) . . . .
C44 N45 C46 C47 0.9(10) . . . .
C53 N45 C46 C47 -179.6(9) . . . .
C44 N43 C47 C46 2.8(11) . . . .
Ir1 N43 C47 C46 178.7(7) . . . .
N45 C46 C47 N43 -2.4(11) . . . .
C50 N49 C48 N52 0.0(11) . . . .
Ir1 N49 C48 N52 177.0(6) . . . .
C50 N49 C48 C44 -179.9(9) . . . .
Ir1 N49 C48 C44 -2.9(11) . . . .
C51 N52 C48 N49 1.2(11) . . . .
C60 N52 C48 N49 -177.5(9) . . . .
C51 N52 C48 C44 -179.0(11) . . . .
C60 N52 C48 C44 2.3(18) . . . .
N45 C44 C48 N49 -176.6(10) . . . .
N43 C44 C48 N49 -0.9(13) . . . .
N45 C44 C48 N52 3.5(19) . . . .
N43 C44 C48 N52 179.3(10) . . . .
C48 N49 C50 C51 -1.2(13) . . . .
Ir1 N49 C50 C51 -177.3(8) . . . .
N49 C50 C51 N52 1.9(14) . . . .
C48 N52 C51 C50 -1.9(13) . . . .
C60 N52 C51 C50 176.9(10) . . . .
C44 N45 C53 C54 57.9(14) . . . .
C46 N45 C53 C54 -121.4(9) . . . .
N45 C53 C54 C55 -81.6(12) . . . .
N45 C53 C54 C59 98.5(10) . . . .
C59 C54 C55 C56 0.1(14) . . . .
C53 C54 C55 C56 -179.9(9) . . . .
C59 C54 C55 C60 177.8(8) . . . .
C53 C54 C55 C60 -2.2(14) . . . .
C54 C55 C56 C57 -1.5(15) . . . .
C60 C55 C56 C57 -179.2(9) . . . .
C55 C56 C57 C58 0.4(15) . . . .
C56 C57 C58 C59 2.2(15) . . . .
C57 C58 C59 C54 -3.6(14) . . . .
C55 C54 C59 C58 2.4(13) . . . .
C53 C54 C59 C58 -177.6(9) . . . .
C48 N52 C60 C55 -63.5(14) . . . .
C51 N52 C60 C55 118.0(11) . . . .
C54 C55 C60 N52 87.9(12) . . . .
C56 C55 C60 N52 -94.5(11) . . . .
C63 O61 C61 C62 -178.6(17) . . . .
C61 O61 C63 C64 178.1(17) . . . .
