#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:52:31 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179351 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/48/4324846.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_4324846
loop_
_publ_author_name
'Yonghao Zheng'
'Andrei S. Batsanov'
'Martin R. Bryce'
_publ_contact_author             'Andrei S.Batsanov'
_publ_contact_author_email       a.s.batsanov@durham.ac.uk
_publ_section_title
;
 Unusual Dinuclear and Mononuclear Cyclometalated Iridium Complexes of
 2,5-Diaryl-1,3,4-oxadiazole Derivatives
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3354
_journal_page_last               3362
_journal_paper_doi               10.1021/ic102153x
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C92 H104 Cl2 F4 Ir2 N8 O4,2(C H2 Cl2)'
_chemical_formula_sum            'C94 H108 Cl6 F4 Ir2 N8 O4'
_chemical_formula_weight         2086.98
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.029(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.2350(5)
_cell_length_b                   15.2472(5)
_cell_length_c                   21.7641(8)
_cell_measurement_reflns_used    8235
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.949
_cell_measurement_theta_min      2.297
_cell_volume                     4651.6(3)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program. 
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. 
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution
;
A short history of SHELX (Sheldrick, 2008)/Bruker
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER SMART CCD 6000'
_diffrn_measurement_method       'Ω scans'
_diffrn_orient_matrix_UB_11      -0.053633
_diffrn_orient_matrix_UB_12      -0.041981
_diffrn_orient_matrix_UB_13      -0.013342
_diffrn_orient_matrix_UB_21      0.007164
_diffrn_orient_matrix_UB_22      0.008175
_diffrn_orient_matrix_UB_23      -0.044532
_diffrn_orient_matrix_UB_31      0.046469
_diffrn_orient_matrix_UB_32      -0.049723
_diffrn_orient_matrix_UB_33      0.003938
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_refln_scan_width         0.3
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            97915
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         1.59
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_target            Mo
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.092
_exptl_absorpt_correction_T_max  0.6764
_exptl_absorpt_correction_T_min  0.3287
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
"'XPREP 6.14 (Bruker, 2003), R(int)=0.101 before correction"
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       tabular
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_refine_diff_density_max         3.808
_refine_diff_density_min         -1.393
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         16837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0247P)²+8.7864P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0713
_reflns_number_gt                13995
_reflns_number_total             16837
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic102153x_si_002_3.cif
_cod_data_source_block           13
_cod_database_code               4324846
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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 0.354643(6) 0.462406(5) 0.500523(4) 0.01245(2) Uani 1 1 d . . .
Cl1 Cl 0.35204(4) 0.52472(4) 0.59920(3) 0.02063(11) Uani 1 1 d . . .
F1 F -0.01605(11) 0.56415(11) 0.43411(8) 0.0283(3) Uani 1 1 d . . .
F2 F 0.10829(11) 0.25962(10) 0.60318(7) 0.0257(3) Uani 1 1 d . . .
O1 O 0.40464(11) 0.69021(11) 0.40751(8) 0.0175(3) Uani 1 1 d . . .
O2 O 0.27253(12) 0.31945(11) 0.34369(8) 0.0175(3) Uani 1 1 d . . .
N1 N 0.42667(13) 0.57471(12) 0.46850(9) 0.0139(3) Uani 1 1 d . . .
N2 N 0.51637(13) 0.60740(12) 0.46137(8) 0.0136(3) Uani 1 1 d . . .
N3 N 0.34439(13) 0.40590(12) 0.41652(9) 0.0141(3) Uani 1 1 d . . .
N4 N 0.37891(14) 0.42817(13) 0.36289(9) 0.0161(3) Uani 1 1 d . . .
C1 C 0.36338(16) 0.62526(14) 0.43540(10) 0.0156(4) Uani 1 1 d . . .
C2 C 0.50064(16) 0.67593(15) 0.42572(10) 0.0155(4) Uani 1 1 d . . .
C3 C 0.28085(16) 0.34413(15) 0.40383(10) 0.0155(4) Uani 1 1 d . . .
C4 C 0.33556(16) 0.37589(15) 0.32072(10) 0.0160(4) Uani 1 1 d . . .
C5 C 0.26271(16) 0.61215(15) 0.43056(11) 0.0166(4) Uani 1 1 d . . .
C6 C 0.24107(15) 0.53668(14) 0.46320(10) 0.0147(4) Uani 1 1 d . . .
C7 C 0.14404(17) 0.52189(16) 0.46314(11) 0.0188(4) Uani 1 1 d . . .
H7 H 0.1241 0.4727 0.4844 0.023 Uiso 1 1 d R . .
C8 C 0.07729(17) 0.57961(16) 0.43174(12) 0.0199(4) Uani 1 1 d . . .
C9 C 0.09885(17) 0.65157(17) 0.39831(12) 0.0221(5) Uani 1 1 d . . .
H9 H 0.0501 0.6881 0.3765 0.026 Uiso 1 1 d R . .
C10 C 0.19446(17) 0.66839(16) 0.39779(12) 0.0195(4) Uani 1 1 d . . .
H10 H 0.2131 0.7172 0.3756 0.023 Uiso 1 1 d R . .
C11 C 0.56372(15) 0.74034(14) 0.40321(10) 0.0151(4) Uani 1 1 d . . .
C12 C 0.59429(16) 0.81354(15) 0.44129(11) 0.0161(4) Uani 1 1 d . . .
C13 C 0.64692(16) 0.87746(15) 0.41693(11) 0.0179(4) Uani 1 1 d . . .
H13 H 0.6690 0.9269 0.4419 0.021 Uiso 1 1 d R . .
C14 C 0.66840(16) 0.87116(16) 0.35672(11) 0.0189(4) Uani 1 1 d . . .
C15 C 0.63679(17) 0.79842(16) 0.32072(11) 0.0202(4) Uani 1 1 d . . .
H15 H 0.6521 0.7934 0.2801 0.024 Uiso 1 1 d R . .
C16 C 0.58291(17) 0.73209(15) 0.34249(11) 0.0181(4) Uani 1 1 d . . .
C17 C 0.56584(17) 0.82432(16) 0.50514(11) 0.0184(4) Uani 1 1 d . . .
H17 H 0.5632 0.7646 0.5237 0.022 Uiso 1 1 d R . .
C18 C 0.46568(19) 0.8650(2) 0.49856(14) 0.0303(6) Uani 1 1 d . . .
H18B H 0.4660 0.9233 0.4796 0.039(6) Uiso 1 1 d R . .
H18C H 0.4477 0.8702 0.5399 0.039(6) Uiso 1 1 d R . .
H18A H 0.4196 0.8275 0.4720 0.039(6) Uiso 1 1 d R . .
C19 C 0.63565(18) 0.87960(17) 0.55058(12) 0.0229(5) Uani 1 1 d . . .
H19A H 0.7007 0.8577 0.5517 0.036(6) Uiso 1 1 d R . .
H19B H 0.6192 0.8757 0.5924 0.036(6) Uiso 1 1 d R . .
H19C H 0.6319 0.9409 0.5368 0.036(6) Uiso 1 1 d R . .
C20 C 0.72415(18) 0.94340(17) 0.33091(13) 0.0231(5) Uani 1 1 d . . .
H20 H 0.7337 0.9253 0.2883 0.028 Uiso 1 1 d R . .
C21 C 0.6696(2) 1.0304(2) 0.32468(19) 0.0382(8) Uani 1 1 d . . .
H21A H 0.6086 1.0228 0.2964 0.043(6) Uiso 1 1 d R . .
H21C H 0.7075 1.0753 0.3079 0.043(6) Uiso 1 1 d R . .
H21B H 0.6577 1.0489 0.3658 0.043(6) Uiso 1 1 d R . .
C22 C 0.82235(19) 0.95588(19) 0.37103(13) 0.0263(5) Uani 1 1 d . . .
H22B H 0.8149 0.9750 0.4129 0.034(5) Uiso 1 1 d R . .
H22C H 0.8578 1.0004 0.3520 0.034(5) Uiso 1 1 d R . .
H22A H 0.8573 0.9003 0.3739 0.034(5) Uiso 1 1 d R . .
C23 C 0.5419(2) 0.65625(17) 0.30062(12) 0.0250(5) Uani 1 1 d . . .
H23 H 0.5239 0.6088 0.3281 0.030 Uiso 1 1 d R . .
C24 C 0.4511(2) 0.6851(2) 0.25691(15) 0.0376(7) Uani 1 1 d . . .
H24C H 0.4663 0.7330 0.2303 0.047(6) Uiso 1 1 d R . .
H24B H 0.4040 0.7052 0.2817 0.047(6) Uiso 1 1 d R . .
H24A H 0.4250 0.6354 0.2308 0.047(6) Uiso 1 1 d R . .
C25 C 0.6138(2) 0.6173(2) 0.26310(14) 0.0347(6) Uani 1 1 d . . .
H25A H 0.5863 0.5649 0.2408 0.043(6) Uiso 1 1 d R . .
H25C H 0.6725 0.6013 0.2916 0.043(6) Uiso 1 1 d R . .
H25B H 0.6285 0.6608 0.2330 0.043(6) Uiso 1 1 d R . .
C26 C 0.23061(16) 0.31629(15) 0.45263(11) 0.0159(4) Uani 1 1 d . . .
C27 C 0.26295(15) 0.36331(14) 0.50866(10) 0.0145(4) Uani 1 1 d . . .
C28 C 0.21945(16) 0.34237(15) 0.55971(11) 0.0171(4) Uani 1 1 d . . .
H28 H 0.2381 0.3712 0.5986 0.021 Uiso 1 1 d R . .
C29 C 0.14909(17) 0.27924(16) 0.55260(12) 0.0195(4) Uani 1 1 d . . .
C30 C 0.11437(18) 0.23612(17) 0.49717(12) 0.0225(5) Uani 1 1 d . . .
H30 H 0.0635 0.1952 0.4944 0.027 Uiso 1 1 d R . .
C31 C 0.15667(17) 0.25502(16) 0.44609(12) 0.0204(4) Uani 1 1 d . . .
H31 H 0.1357 0.2268 0.4072 0.024 Uiso 1 1 d R . .
C32 C 0.34526(16) 0.37480(15) 0.25462(10) 0.0161(4) Uani 1 1 d . . .
C33 C 0.43399(16) 0.35146(15) 0.23879(10) 0.0166(4) Uani 1 1 d . . .
C34 C 0.44412(17) 0.36190(16) 0.17662(11) 0.0189(4) Uani 1 1 d . . .
H34 H 0.5029 0.3462 0.1646 0.023 Uiso 1 1 d R . .
C35 C 0.37105(18) 0.39451(16) 0.13163(11) 0.0199(4) Uani 1 1 d . . .
C36 C 0.28400(18) 0.41555(17) 0.14874(11) 0.0218(5) Uani 1 1 d . . .
H36 H 0.2335 0.4366 0.1179 0.026 Uiso 1 1 d R . .
C37 C 0.26938(17) 0.40644(16) 0.21008(11) 0.0193(4) Uani 1 1 d . . .
C38 C 0.51370(17) 0.31476(18) 0.28730(11) 0.0216(5) Uani 1 1 d . . .
H38 H 0.5157 0.3500 0.3263 0.026 Uiso 1 1 d R . .
C39 C 0.4922(2) 0.2196(2) 0.30267(18) 0.0407(8) Uani 1 1 d . . .
H39B H 0.4307 0.2169 0.3170 0.059(7) Uiso 1 1 d R . .
H39C H 0.5426 0.1977 0.3356 0.059(7) Uiso 1 1 d R . .
H39A H 0.4895 0.1833 0.2652 0.059(7) Uiso 1 1 d R . .
C40 C 0.61222(19) 0.3204(2) 0.26890(14) 0.0316(6) Uani 1 1 d . . .
H40A H 0.6145 0.2818 0.2332 0.044(6) Uiso 1 1 d R . .
H40C H 0.6608 0.3021 0.3042 0.044(6) Uiso 1 1 d R . .
H40B H 0.6246 0.3810 0.2575 0.044(6) Uiso 1 1 d R . .
C41 C 0.3891(2) 0.41131(18) 0.06573(12) 0.0252(5) Uani 1 1 d . . .
H41 H 0.4476 0.3779 0.0603 0.030 Uiso 1 1 d R . .
C42 C 0.4094(2) 0.5090(2) 0.05831(14) 0.0307(6) Uani 1 1 d . . .
H42B H 0.4275 0.5191 0.0175 0.039(6) Uiso 1 1 d R . .
H42C H 0.4616 0.5273 0.0913 0.039(6) Uiso 1 1 d R . .
H42A H 0.3520 0.5430 0.0614 0.039(6) Uiso 1 1 d R . .
C43 C 0.3075(3) 0.3813(2) 0.01521(13) 0.0373(7) Uani 1 1 d . . .
H43A H 0.2930 0.3196 0.0220 0.050(7) Uiso 1 1 d R . .
H43C H 0.3261 0.3879 -0.0258 0.050(7) Uiso 1 1 d R . .
H43B H 0.2509 0.4171 0.0170 0.050(7) Uiso 1 1 d R . .
C44 C 0.17706(19) 0.4370(2) 0.22950(12) 0.0273(5) Uani 1 1 d . . .
H44 H 0.1660 0.3997 0.2653 0.033 Uiso 1 1 d R . .
C45 C 0.1879(3) 0.5322(3) 0.25256(18) 0.0489(10) Uani 1 1 d . . .
H45A H 0.1972 0.5706 0.2180 0.066(8) Uiso 1 1 d R . .
H45C H 0.2433 0.5368 0.2862 0.066(8) Uiso 1 1 d R . .
H45B H 0.1303 0.5501 0.2682 0.066(8) Uiso 1 1 d R . .
C46 C 0.08989(19) 0.4280(2) 0.17793(14) 0.0309(6) Uani 1 1 d . . .
H46B H 0.0949 0.4697 0.1444 0.040(6) Uiso 1 1 d R . .
H46C H 0.0320 0.4402 0.1950 0.040(6) Uiso 1 1 d R . .
H46A H 0.0869 0.3681 0.1613 0.040(6) Uiso 1 1 d R . .
Cl2 Cl -0.13314(9) 0.26902(8) 0.39191(6) 0.0675(3) Uani 1 1 d . A .
Cl3A Cl -0.03925(12) 0.40379(9) 0.33154(5) 0.0686(4) Uani 0.95 1 d P A 1
Cl3B Cl -0.0899(16) 0.4319(15) 0.3269(10) 0.047(4) Uiso 0.05 1 d P A 2
C47 C -0.1011(3) 0.3798(3) 0.39340(19) 0.0519(9) Uani 1 1 d . . .
H472 H -0.0600 0.3937 0.4337 0.062 Uiso 1 1 d R A .
H471 H -0.1593 0.4163 0.3896 0.062 Uiso 1 1 d 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'
Cl Cl 0.1484 0.1585 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 1.00 0.0700
0.00 1.00 -1.00 0.0700
0.00 0.00 -1.00 0.1250
0.00 0.00 1.00 0.1250
1.00 1.00 0.00 0.1500
-1.00 0.00 0.00 0.2100
2.00 0.00 -3.00 0.2400
0.00 -1.00 -1.00 0.1100
0.00 1.00 1.00 0.1500
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
F1 C8 C7 117.5(2) . .
F1 C8 C9 117.8(2) . .
F2 C29 C28 117.8(2) . .
F2 C29 C30 117.4(2) . .
O1 C1 C5 125.3(2) . .
O1 C2 C11 115.64(19) . .
O2 C3 C26 131.4(2) . .
O2 C4 C32 121.29(19) . .
N1 Ir Cl1 93.32(5) . .
N1 N2 Ir 120.76(13) . 3_666
N1 C1 O1 111.70(19) . .
N1 C1 C5 123.0(2) . .
N2 Ir Cl1 89.77(5) 3_666 .
N2 Ir N1 95.42(7) 3_666 .
N2 N1 Ir 143.55(14) . .
N2 C2 O1 111.10(19) . .
N2 C2 C11 133.2(2) . .
N3 Ir Cl1 174.70(5) . .
N3 Ir N1 90.55(7) . .
N3 Ir N2 93.47(7) . 3_666
N3 Ir C6 87.03(8) . .
N3 Ir C27 79.23(8) . .
N3 C3 O2 110.39(19) . .
N3 C3 C26 118.1(2) . .
N4 N3 Ir 133.11(15) . .
N4 C4 O2 112.56(19) . .
N4 C4 C32 126.1(2) . .
C1 O1 C2 104.08(17) . .
C1 N1 Ir 108.91(14) . .
C1 N1 N2 106.46(18) . .
C2 N2 Ir 132.33(15) . 3_666
C2 N2 N1 106.64(18) . .
C3 O2 C4 102.86(17) . .
C3 N3 Ir 116.25(15) . .
C3 N3 N4 109.51(18) . .
C4 N4 N3 104.62(18) . .
C5 C6 Ir 115.34(16) . .
C5 C10 H10 120.7 . .
C6 Ir Cl1 90.11(6) . .
C6 Ir N1 79.57(8) . .
C6 Ir N2 174.97(8) . 3_666
C6 Ir C27 88.31(9) . .
C6 C5 C1 112.3(2) . .
C6 C7 H7 120.3 . .
C7 C6 Ir 129.01(17) . .
C7 C6 C5 115.6(2) . .
C8 C7 C6 119.4(2) . .
C8 C7 H7 120.3 . .
C8 C9 H9 121.3 . .
C8 C9 C10 117.4(2) . .
C9 C8 C7 124.7(2) . .
C9 C10 C5 118.6(2) . .
C9 C10 H10 120.7 . .
C10 C5 C1 123.4(2) . .
C10 C5 C6 124.3(2) . .
C10 C9 H9 121.3 . .
C11 C12 C17 121.1(2) . .
C11 C16 C23 121.0(2) . .
C12 C11 C2 118.4(2) . .
C12 C13 H13 119.0 . .
C12 C13 C14 122.0(2) . .
C12 C17 H17 107.8 . .
C12 C17 C18 110.4(2) . .
C12 C17 C19 113.8(2) . .
C13 C12 C11 117.5(2) . .
C13 C12 C17 121.3(2) . .
C13 C14 C20 120.6(2) . .
C14 C13 H13 119.0 . .
C14 C15 H15 119.0 . .
C14 C15 C16 122.0(2) . .
C14 C20 H20 107.8 . .
C14 C20 C21 111.8(2) . .
C14 C20 C22 111.3(2) . .
C15 C14 C13 118.8(2) . .
C15 C14 C20 120.6(2) . .
C15 C16 C11 117.5(2) . .
C15 C16 C23 121.4(2) . .
C16 C11 C2 119.0(2) . .
C16 C11 C12 122.2(2) . .
C16 C15 H15 119.0 . .
C16 C23 H23 107.6 . .
C16 C23 C24 110.4(2) . .
C16 C23 C25 113.0(2) . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
C17 C18 H18A 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
C18 C17 H17 107.8 . .
H18B C18 H18C 109.5 . .
H18B C18 H18A 109.5 . .
H18C C18 H18A 109.5 . .
C19 C17 H17 107.8 . .
C19 C17 C18 109.0(2) . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C20 C21 H21A 109.5 . .
C20 C21 H21C 109.5 . .
C20 C21 H21B 109.5 . .
C20 C22 H22B 109.5 . .
C20 C22 H22C 109.5 . .
C20 C22 H22A 109.5 . .
C21 C20 H20 107.8 . .
H21A C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21C C21 H21B 109.5 . .
C22 C20 H20 107.8 . .
C22 C20 C21 110.0(2) . .
H22B C22 H22C 109.5 . .
H22B C22 H22A 109.5 . .
H22C C22 H22A 109.5 . .
C23 C24 H24C 109.5 . .
C23 C24 H24B 109.5 . .
C23 C24 H24A 109.5 . .
C23 C25 H25A 109.5 . .
C23 C25 H25C 109.5 . .
C23 C25 H25B 109.5 . .
C24 C23 H23 107.6 . .
C24 C23 C25 110.4(2) . .
H24C C24 H24B 109.5 . .
H24C C24 H24A 109.5 . .
H24B C24 H24A 109.5 . .
C25 C23 H23 107.6 . .
H25A C25 H25C 109.5 . .
H25A C25 H25B 109.5 . .
H25C C25 H25B 109.5 . .
C26 C27 Ir 114.78(15) . .
C26 C31 H31 120.5 . .
C27 Ir Cl1 96.24(6) . .
C27 Ir N1 164.58(8) . .
C27 Ir N2 96.69(8) . 3_666
C27 C26 C3 110.81(19) . .
C27 C28 H28 120.5 . .
C28 C27 Ir 128.36(17) . .
C28 C27 C26 116.4(2) . .
C28 C29 C30 124.8(2) . .
C29 C28 C27 118.9(2) . .
C29 C28 H28 120.5 . .
C29 C30 H30 121.3 . .
C30 C31 C26 118.9(2) . .
C30 C31 H31 120.6 . .
C31 C26 C3 125.7(2) . .
C31 C26 C27 123.5(2) . .
C31 C30 C29 117.5(2) . .
C31 C30 H30 121.3 . .
C32 C33 C38 121.1(2) . .
C32 C37 C44 120.7(2) . .
C33 C32 C4 118.9(2) . .
C33 C34 H34 118.9 . .
C33 C38 H38 107.5 . .
C33 C38 C39 110.4(2) . .
C33 C38 C40 114.0(2) . .
C34 C33 C32 117.1(2) . .
C34 C33 C38 121.8(2) . .
C34 C35 C36 119.0(2) . .
C34 C35 C41 119.7(2) . .
C35 C34 C33 122.2(2) . .
C35 C34 H34 118.9 . .
C35 C36 H36 119.3 . .
C35 C36 C37 121.5(2) . .
C35 C41 H41 107.9 . .
C35 C41 C42 109.2(2) . .
C35 C41 C43 113.4(2) . .
C36 C35 C41 121.2(2) . .
C36 C37 C32 118.0(2) . .
C36 C37 C44 121.1(2) . .
C37 C32 C4 118.7(2) . .
C37 C32 C33 122.1(2) . .
C37 C36 H36 119.3 . .
C37 C44 H44 107.7 . .
C37 C44 C45 109.7(3) . .
C37 C44 C46 113.5(2) . .
C38 C39 H39B 109.5 . .
C38 C39 H39C 109.5 . .
C38 C39 H39A 109.5 . .
C38 C40 H40A 109.5 . .
C38 C40 H40C 109.5 . .
C38 C40 H40B 109.5 . .
C39 C38 H38 107.5 . .
H39B C39 H39C 109.5 . .
H39B C39 H39A 109.5 . .
H39C C39 H39A 109.5 . .
C40 C38 H38 107.5 . .
C40 C38 C39 109.8(2) . .
H40A C40 H40C 109.5 . .
H40A C40 H40B 109.5 . .
H40C C40 H40B 109.5 . .
C41 C42 H42B 109.5 . .
C41 C42 H42C 109.5 . .
C41 C42 H42A 109.5 . .
C41 C43 H43A 109.5 . .
C41 C43 H43C 109.5 . .
C41 C43 H43B 109.5 . .
C42 C41 H41 107.9 . .
H42B C42 H42C 109.5 . .
H42B C42 H42A 109.5 . .
H42C C42 H42A 109.5 . .
C43 C41 H41 107.9 . .
C43 C41 C42 110.5(2) . .
H43A C43 H43C 109.5 . .
H43A C43 H43B 109.5 . .
H43C C43 H43B 109.5 . .
C44 C45 H45A 109.5 . .
C44 C45 H45C 109.5 . .
C44 C45 H45B 109.5 . .
C44 C46 H46B 109.5 . .
C44 C46 H46C 109.5 . .
C44 C46 H46A 109.5 . .
C45 C44 H44 107.7 . .
H45A C45 H45C 109.5 . .
H45A C45 H45B 109.5 . .
H45C C45 H45B 109.5 . .
C46 C44 H44 107.7 . .
C46 C44 C45 110.4(2) . .
H46B C46 H46C 109.5 . .
H46B C46 H46A 109.5 . .
H46C C46 H46A 109.5 . .
Cl2 C47 Cl3A 110.4(2) . .
Cl2 C47 H472 109.6 . .
Cl2 C47 H471 109.3 . .
Cl3A C47 H472 109.5 . .
Cl3A C47 H471 109.9 . .
Cl3B C47 Cl2 120.2(8) . .
H472 C47 H471 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir Cl1 2.3545(6) .
Ir N1 2.1721(18) .
Ir N2 2.1591(18) 3_666
Ir N3 2.0033(19) .
Ir C6 2.025(2) .
Ir C27 2.025(2) .
F1 C8 1.359(3) .
F2 C29 1.364(3) .
O1 C1 1.348(3) .
O1 C2 1.372(3) .
O2 C3 1.347(3) .
O2 C4 1.397(3) .
N1 N2 1.404(2) .
N1 C1 1.303(3) .
N2 Ir 2.1591(18) 3_666
N2 C2 1.297(3) .
N3 N4 1.385(3) .
N3 C3 1.302(3) .
N4 C4 1.289(3) .
C1 C5 1.433(3) .
C2 C11 1.471(3) .
C3 C26 1.444(3) .
C4 C32 1.469(3) .
C5 C6 1.414(3) .
C5 C10 1.395(3) .
C6 C7 1.399(3) .
C7 H7 0.9500 .
C7 C8 1.385(3) .
C8 C9 1.380(3) .
C9 H9 0.9500 .
C9 C10 1.387(3) .
C10 H10 0.9500 .
C11 C12 1.413(3) .
C11 C16 1.401(3) .
C12 C13 1.389(3) .
C12 C17 1.522(3) .
C13 H13 0.9500 .
C13 C14 1.400(3) .
C14 C15 1.387(4) .
C14 C20 1.521(3) .
C15 H15 0.9500 .
C15 C16 1.401(3) .
C16 C23 1.524(3) .
C17 H17 0.9999 .
C17 C18 1.539(4) .
C17 C19 1.528(3) .
C18 H18B 0.9801 .
C18 H18C 0.9799 .
C18 H18A 0.9800 .
C19 H19A 0.9801 .
C19 H19B 0.9799 .
C19 H19C 0.9800 .
C20 H20 1.0001 .
C20 C21 1.532(4) .
C20 C22 1.526(4) .
C21 H21A 0.9800 .
C21 H21C 0.9800 .
C21 H21B 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9799 .
C22 H22A 0.9800 .
C23 H23 1.0001 .
C23 C24 1.530(4) .
C23 C25 1.535(4) .
C24 H24C 0.9801 .
C24 H24B 0.9799 .
C24 H24A 0.9799 .
C25 H25A 0.9799 .
C25 H25C 0.9801 .
C25 H25B 0.9799 .
C26 C27 1.420(3) .
C26 C31 1.396(3) .
C27 C28 1.400(3) .
C28 H28 0.9501 .
C28 C29 1.378(3) .
C29 C30 1.387(4) .
C30 H30 0.9501 .
C30 C31 1.384(3) .
C31 H31 0.9499 .
C32 C33 1.412(3) .
C32 C37 1.405(3) .
C33 C34 1.395(3) .
C33 C38 1.516(3) .
C34 H34 0.9499 .
C34 C35 1.390(3) .
C35 C36 1.392(3) .
C35 C41 1.522(3) .
C36 H36 0.9500 .
C36 C37 1.393(3) .
C37 C44 1.522(3) .
C38 H38 1.0000 .
C38 C39 1.532(4) .
C38 C40 1.527(4) .
C39 H39B 0.9800 .
C39 H39C 0.9799 .
C39 H39A 0.9801 .
C40 H40A 0.9801 .
C40 H40C 0.9799 .
C40 H40B 0.9801 .
C41 H41 0.9999 .
C41 C42 1.531(4) .
C41 C43 1.524(4) .
C42 H42B 0.9802 .
C42 H42C 0.9800 .
C42 H42A 0.9799 .
C43 H43A 0.9800 .
C43 H43C 0.9799 .
C43 H43B 0.9801 .
C44 H44 1.0000 .
C44 C45 1.535(5) .
C44 C46 1.528(4) .
C45 H45A 0.9801 .
C45 H45C 0.9801 .
C45 H45B 0.9801 .
C46 H46B 0.9799 .
C46 H46C 0.9800 .
C46 H46A 0.9800 .
Cl2 C47 1.748(4) .
Cl3A C47 1.771(4) .
Cl3B C47 1.68(2) .
C47 H472 0.9901 .
C47 H471 0.9897 .
