# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1814938'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 F5 N O'
_chemical_formula_sum            'C11 H8 F5 N O'
_chemical_formula_weight         265.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8061(4)
_cell_length_b                   8.7128(3)
_cell_length_c                   11.6109(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.422(3)
_cell_angle_gamma                90
_cell_volume                     1093.15(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    3596
_cell_measurement_theta_min      4.1980
_cell_measurement_theta_max      27.2020

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81289
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            7398
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.472
_diffrn_reflns_theta_max         27.032
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2234
_reflns_number_gt                2042
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.3979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2234
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36019(11) 0.62229(14) 0.27072(10) 0.0208(3) Uani 1 1 d . . . . .
C2 C 0.31138(12) 0.53622(14) 0.18025(11) 0.0235(3) Uani 1 1 d . . . . .
F2 F 0.38340(7) 0.43227(9) 0.12761(6) 0.0309(2) Uani 1 1 d . . . . .
C3 C 0.19077(13) 0.55315(16) 0.14233(11) 0.0284(3) Uani 1 1 d . . . . .
F3 F 0.14813(8) 0.46825(11) 0.05446(7) 0.0402(2) Uani 1 1 d . . . . .
C4 C 0.11476(12) 0.65731(17) 0.19650(12) 0.0303(3) Uani 1 1 d . . . . .
F4 F -0.00232(8) 0.67724(12) 0.16029(9) 0.0443(3) Uani 1 1 d . . . . .
C5 C 0.15979(12) 0.74267(16) 0.28817(12) 0.0288(3) Uani 1 1 d . . . . .
F5 F 0.08486(8) 0.84298(11) 0.34080(8) 0.0425(2) Uani 1 1 d . . . . .
C6 C 0.28069(12) 0.72539(15) 0.32412(11) 0.0238(3) Uani 1 1 d . . . . .
F6 F 0.32228(7) 0.81093(9) 0.41232(7) 0.0315(2) Uani 1 1 d . . . . .
N7 N 0.48210(9) 0.60139(13) 0.31085(9) 0.0216(2) Uani 1 1 d . . . . .
H7 H 0.4928(15) 0.570(2) 0.3823(16) 0.036(4) Uiso 1 1 d . . . . .
C8 C 0.58557(12) 0.62668(14) 0.24789(11) 0.0219(3) Uani 1 1 d . . . . .
C81 C 0.57085(14) 0.69323(18) 0.12965(12) 0.0292(3) Uani 1 1 d . . . . .
H81A H 0.5414(17) 0.618(2) 0.0752(17) 0.048(5) Uiso 1 1 d . . . . .
H81B H 0.6479(19) 0.731(2) 0.1006(17) 0.051(5) Uiso 1 1 d . . . . .
H81C H 0.5119(17) 0.777(2) 0.1289(15) 0.043(5) Uiso 1 1 d . . . . .
C9 C 0.70089(12) 0.59787(15) 0.29276(11) 0.0242(3) Uani 1 1 d . . . . .
H9 H 0.7673(14) 0.6233(18) 0.2468(13) 0.026(4) Uiso 1 1 d . . . . .
C10 C 0.72298(11) 0.54172(15) 0.40658(11) 0.0236(3) Uani 1 1 d . . . . .
O10 O 0.63870(8) 0.50472(12) 0.47396(8) 0.0270(2) Uani 1 1 d . . . . .
C11 C 0.85592(14) 0.5303(2) 0.44733(15) 0.0375(4) Uani 1 1 d . . . . .
H11A H 0.877(3) 0.613(4) 0.495(3) 0.105(10) Uiso 1 1 d . . . . .
H11B H 0.914(2) 0.527(3) 0.383(2) 0.063(6) Uiso 1 1 d . . . . .
H11C H 0.867(2) 0.437(3) 0.490(2) 0.070(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3914(18) . ?
C1 C6 1.3919(18) . ?
C1 N7 1.4059(16) . ?
C2 F2 1.3441(15) . ?
C2 C3 1.3805(19) . ?
C3 F3 1.3392(15) . ?
C3 C4 1.379(2) . ?
C4 F4 1.3415(15) . ?
C4 C5 1.384(2) . ?
C5 F5 1.3417(16) . ?
C5 C6 1.3768(18) . ?
C6 F6 1.3414(15) . ?
N7 C8 1.3584(16) . ?
N7 H7 0.881(18) . ?
C8 C9 1.3703(18) . ?
C8 C81 1.4977(18) . ?
C81 H81A 0.96(2) . ?
C81 H81B 0.96(2) . ?
C81 H81C 0.97(2) . ?
C9 C10 1.4276(18) . ?
C9 H9 0.925(16) . ?
C10 O10 1.2474(16) . ?
C10 C11 1.5123(18) . ?
C11 H11A 0.93(3) . ?
C11 H11B 0.97(2) . ?
C11 H11C 0.96(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.90(11) . . ?
C2 C1 N7 121.97(11) . . ?
C6 C1 N7 121.06(11) . . ?
F2 C2 C3 118.39(11) . . ?
F2 C2 C1 119.27(11) . . ?
C3 C2 C1 122.34(12) . . ?
F3 C3 C4 120.55(12) . . ?
F3 C3 C2 120.18(13) . . ?
C4 C3 C2 119.28(12) . . ?
F4 C4 C3 120.39(13) . . ?
F4 C4 C5 119.79(13) . . ?
C3 C4 C5 119.82(12) . . ?
F5 C5 C6 120.50(13) . . ?
F5 C5 C4 119.37(12) . . ?
C6 C5 C4 120.12(13) . . ?
F6 C6 C5 118.85(12) . . ?
F6 C6 C1 119.61(11) . . ?
C5 C6 C1 121.53(12) . . ?
C8 N7 C1 125.00(11) . . ?
C8 N7 H7 117.1(11) . . ?
C1 N7 H7 117.9(11) . . ?
N7 C8 C9 121.03(12) . . ?
N7 C8 C81 118.28(11) . . ?
C9 C8 C81 120.64(12) . . ?
C8 C81 H81A 111.6(12) . . ?
C8 C81 H81B 111.6(12) . . ?
H81A C81 H81B 106.7(16) . . ?
C8 C81 H81C 111.4(11) . . ?
H81A C81 H81C 107.1(15) . . ?
H81B C81 H81C 108.1(16) . . ?
C8 C9 C10 124.07(12) . . ?
C8 C9 H9 116.4(9) . . ?
C10 C9 H9 119.4(9) . . ?
O10 C10 C9 123.45(11) . . ?
O10 C10 C11 118.89(12) . . ?
C9 C10 C11 117.65(12) . . ?
C10 C11 H11A 110.9(18) . . ?
C10 C11 H11B 112.1(13) . . ?
H11A C11 H11B 109(2) . . ?
C10 C11 H11C 109.6(14) . . ?
H11A C11 H11C 109(2) . . ?
H11B C11 H11C 106.8(18) . . ?

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
C6 C1 C2 F2 -178.37(11) . . . . ?
N7 C1 C2 F2 -1.55(18) . . . . ?
C6 C1 C2 C3 1.42(18) . . . . ?
N7 C1 C2 C3 178.24(11) . . . . ?
F2 C2 C3 F3 -0.58(18) . . . . ?
C1 C2 C3 F3 179.63(11) . . . . ?
F2 C2 C3 C4 178.90(11) . . . . ?
C1 C2 C3 C4 -0.89(19) . . . . ?
F3 C3 C4 F4 -1.4(2) . . . . ?
C2 C3 C4 F4 179.15(12) . . . . ?
F3 C3 C4 C5 179.14(12) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
F4 C4 C5 F5 0.9(2) . . . . ?
C3 C4 C5 F5 -179.56(12) . . . . ?
F4 C4 C5 C6 -178.51(12) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
F5 C5 C6 F6 -0.24(19) . . . . ?
C4 C5 C6 F6 179.22(12) . . . . ?
F5 C5 C6 C1 -179.88(12) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C2 C1 C6 F6 179.61(11) . . . . ?
N7 C1 C6 F6 2.76(18) . . . . ?
C2 C1 C6 C5 -0.75(19) . . . . ?
N7 C1 C6 C5 -177.60(12) . . . . ?
C2 C1 N7 C8 63.17(17) . . . . ?
C6 C1 N7 C8 -120.14(14) . . . . ?
C1 N7 C8 C9 -177.59(12) . . . . ?
C1 N7 C8 C81 4.93(19) . . . . ?
N7 C8 C9 C10 -0.6(2) . . . . ?
C81 C8 C9 C10 176.82(13) . . . . ?
C8 C9 C10 O10 4.4(2) . . . . ?
C8 C9 C10 C11 -174.20(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7 O10 0.881(18) 1.978(17) 2.6669(14) 134.0(15) .
N7 H7 O10 0.881(18) 2.293(18) 2.9749(14) 134.1(14) 3_666
C81 H81A F2 0.96(2) 2.431(19) 3.0451(17) 121.2(14) .
C81 H81A F2 0.96(2) 2.53(2) 3.2224(16) 128.3(14) 3_665

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1814939'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H27 F Ir N3 O'
_chemical_formula_weight         740.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.3067(4)
_cell_length_b                   18.7491(4)
_cell_length_c                   19.7051(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.847(3)
_cell_angle_gamma                90
_cell_volume                     5701.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    10921
_cell_measurement_theta_min      3.4210
_cell_measurement_theta_max      26.3230

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             2912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    4.726
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.65156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            24228
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.062
_diffrn_reflns_theta_max         26.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             10919
_reflns_number_gt                8514
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_refine_special_details          
'disordered Ph group in one of the symmetry-independent molecules'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0129P)²+75.9272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10919
_refine_ls_number_parameters     843
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
Ir1A Ir 0.98498(2) 0.79773(2) 0.19570(2) 0.01927(9) Uani 1 1 d . . . . .
C1A C 1.0536(5) 0.6975(5) 0.3276(4) 0.030(2) Uani 1 1 d D . . . .
C2A C 1.0151(6) 0.7073(5) 0.3800(5) 0.036(2) Uani 1 1 d D . . . .
F2A F 0.9274(4) 0.7145(4) 0.3579(4) 0.068(2) Uani 1 1 d D . . . .
C3A C 1.0586(7) 0.7067(5) 0.4527(5) 0.049(3) Uani 1 1 d D . . . .
H3A H 1.0289 0.7119 0.4867 0.058 Uiso 1 1 calc R U . . .
C4A C 1.1472(7) 0.6981(6) 0.4738(5) 0.051(3) Uani 1 1 d D . . . .
H4A H 1.1799 0.6978 0.5234 0.062 Uiso 1 1 calc R U . . .
C5A C 1.1890(6) 0.6899(5) 0.4231(6) 0.049(3) Uani 1 1 d D . . . .
H5A H 1.2502 0.6846 0.4388 0.058 Uiso 1 1 calc R U . . .
C6A C 1.1437(6) 0.6893(5) 0.3500(5) 0.040(3) Uani 1 1 d D . . . .
H6A H 1.1733 0.6835 0.3159 0.048 Uiso 1 1 calc R U . . .
N7A N 1.0049(4) 0.6976(4) 0.2522(4) 0.0239(16) Uani 1 1 d . . . . .
C8A C 0.9793(5) 0.6371(5) 0.2210(5) 0.028(2) Uani 1 1 d . . . . .
C81A C 0.9836(6) 0.5701(5) 0.2648(5) 0.030(2) Uani 1 1 d . . . . .
H81A H 1.0428 0.5636 0.2975 0.045 Uiso 1 1 calc R U . . .
H81B H 0.9670 0.5290 0.2327 0.045 Uiso 1 1 calc R U . . .
H81C H 0.9437 0.5745 0.2926 0.045 Uiso 1 1 calc R U . . .
C9A C 0.9457(5) 0.6273(5) 0.1445(5) 0.028(2) Uani 1 1 d . . . . .
H9A H 0.9175 0.5831 0.1284 0.033 Uiso 1 1 calc R U . . .
C10A C 0.9496(5) 0.6739(5) 0.0921(5) 0.0222(19) Uani 1 1 d . . . . .
O10A O 0.9704(4) 0.7399(3) 0.0993(3) 0.0248(13) Uani 1 1 d . . . . .
C11A C 0.9294(6) 0.6463(5) 0.0162(5) 0.030(2) Uani 1 1 d . . . . .
H11A H 0.8832 0.6752 -0.0164 0.044 Uiso 1 1 calc R U . . .
H11B H 0.9105 0.5965 0.0140 0.044 Uiso 1 1 calc R U . . .
H11C H 0.9815 0.6494 0.0018 0.044 Uiso 1 1 calc R U . . .
N12A N 0.8520(4) 0.7943(4) 0.1714(4) 0.0250(16) Uani 1 1 d . . . . .
C13A C 0.8066(6) 0.7482(5) 0.1978(6) 0.034(2) Uani 1 1 d . . . . .
H13A H 0.8358 0.7131 0.2317 0.041 Uiso 1 1 calc R U . . .
C14A C 0.7155(6) 0.7524(6) 0.1748(6) 0.047(3) Uani 1 1 d . . . . .
H14A H 0.6837 0.7197 0.1934 0.056 Uiso 1 1 calc R U . . .
C15A C 0.6720(6) 0.8025(7) 0.1264(6) 0.045(3) Uani 1 1 d . . . . .
H15A H 0.6105 0.8045 0.1114 0.054 Uiso 1 1 calc R U . . .
C16A C 0.7185(6) 0.8507(6) 0.0992(6) 0.040(3) Uani 1 1 d . . . . .
C17A C 0.6816(7) 0.9066(7) 0.0470(6) 0.050(3) Uani 1 1 d . . . . .
H17A H 0.6204 0.9113 0.0276 0.060 Uiso 1 1 calc R U . . .
C18A C 0.7329(7) 0.9522(6) 0.0257(6) 0.047(3) Uani 1 1 d . . . . .
H18A H 0.7066 0.9871 -0.0096 0.056 Uiso 1 1 calc R U . . .
C19A C 0.8239(7) 0.9496(6) 0.0541(5) 0.039(3) Uani 1 1 d . . . . .
C20A C 0.8797(8) 0.9992(6) 0.0381(5) 0.046(3) Uani 1 1 d . . . . .
H20A H 0.8565 1.0374 0.0060 0.055 Uiso 1 1 calc R U . . .
C21A C 0.9666(7) 0.9925(5) 0.0686(5) 0.040(3) Uani 1 1 d . . . . .
H21A H 1.0034 1.0272 0.0584 0.049 Uiso 1 1 calc R U . . .
C22A C 1.0038(6) 0.9363(5) 0.1145(5) 0.032(2) Uani 1 1 d . . . . .
H22A H 1.0652 0.9328 0.1328 0.038 Uiso 1 1 calc R U . . .
C23A C 0.9548(6) 0.8856(5) 0.1344(5) 0.027(2) Uani 1 1 d . . . . .
C24A C 0.8629(6) 0.8948(5) 0.1027(5) 0.030(2) Uani 1 1 d . . . . .
C25A C 0.8102(6) 0.8458(5) 0.1245(5) 0.030(2) Uani 1 1 d . . . . .
N26A N 1.1159(4) 0.8084(4) 0.2192(4) 0.0223(15) Uani 1 1 d . . . . .
C27A C 1.1643(5) 0.7819(5) 0.1812(5) 0.028(2) Uani 1 1 d . . . . .
H27A H 1.1367 0.7574 0.1376 0.033 Uiso 1 1 calc R U . . .
C28A C 1.2543(6) 0.7899(5) 0.2046(5) 0.034(2) Uani 1 1 d . . . . .
H28A H 1.2876 0.7704 0.1775 0.040 Uiso 1 1 calc R U . . .
C29A C 1.2945(6) 0.8264(5) 0.2679(5) 0.030(2) Uani 1 1 d . . . . .
H29A H 1.3558 0.8314 0.2846 0.037 Uiso 1 1 calc R U . . .
C30A C 1.2451(6) 0.8561(5) 0.3073(5) 0.030(2) Uani 1 1 d . . . . .
C31A C 1.2787(6) 0.8946(5) 0.3725(5) 0.034(2) Uani 1 1 d . . . . .
H31A H 1.3394 0.9024 0.3920 0.040 Uiso 1 1 calc R U . . .
C32A C 1.2260(7) 0.9201(5) 0.4071(5) 0.039(3) Uani 1 1 d . . . . .
H32A H 1.2512 0.9449 0.4510 0.047 Uiso 1 1 calc R U . . .
C33A C 1.1332(6) 0.9115(5) 0.3808(5) 0.028(2) Uani 1 1 d . . . . .
C34A C 1.0756(7) 0.9386(5) 0.4137(5) 0.031(2) Uani 1 1 d . . . . .
H34A H 1.0964 0.9643 0.4575 0.037 Uiso 1 1 calc R U . . .
C35A C 0.9878(7) 0.9272(5) 0.3814(5) 0.032(2) Uani 1 1 d . . . . .
H35A H 0.9487 0.9472 0.4029 0.038 Uiso 1 1 calc R U . . .
C36A C 0.9536(6) 0.8869(5) 0.3175(5) 0.029(2) Uani 1 1 d . . . . .
H36A H 0.8928 0.8801 0.2976 0.034 Uiso 1 1 calc R U . . .
C37A C 1.0083(5) 0.8574(5) 0.2838(5) 0.0232(19) Uani 1 1 d . . . . .
C38A C 1.0985(5) 0.8726(4) 0.3163(5) 0.0224(18) Uani 1 1 d . . . . .
C39A C 1.1550(5) 0.8455(4) 0.2803(5) 0.0246(19) Uani 1 1 d . . . . .
Ir1B Ir 0.49049(2) 0.54689(2) 0.29433(2) 0.01443(8) Uani 1 1 d . . . . .
C1B C 0.4244(7) 0.4365(10) 0.1764(5) 0.020(4) Uani 0.623(14) 1 d D U P A 1
C2B C 0.4535(8) 0.4518(11) 0.1194(6) 0.023(4) Uani 0.623(14) 1 d D U P A 1
F2B F 0.5409(5) 0.4640(5) 0.1346(4) 0.037(3) Uani 0.623(14) 1 d D U P A 1
C3B C 0.4015(9) 0.4512(10) 0.0487(6) 0.035(4) Uani 0.623(14) 1 d D U P A 1
H3B H 0.4239 0.4620 0.0109 0.041 Uiso 0.623(14) 1 calc R U P A 1
C4B C 0.3153(8) 0.4342(9) 0.0353(7) 0.034(5) Uani 0.623(14) 1 d D U P A 1
H4B H 0.2774 0.4325 -0.0128 0.040 Uiso 0.623(14) 1 calc R U P A 1
C5B C 0.2831(8) 0.4197(9) 0.0908(8) 0.039(5) Uani 0.623(14) 1 d D U P A 1
H5B H 0.2232 0.4099 0.0803 0.047 Uiso 0.623(14) 1 calc R U P A 1
C6B C 0.3373(8) 0.4192(10) 0.1617(7) 0.028(4) Uani 0.623(14) 1 d D U P A 1
H6B H 0.3153 0.4074 0.1994 0.033 Uiso 0.623(14) 1 calc R U P A 1
C1C C 0.4381(9) 0.4384(16) 0.1679(7) 0.016(6) Uani 0.377(14) 1 d D U P A 2
C2C C 0.3507(10) 0.4236(15) 0.1380(7) 0.014(6) Uani 0.377(14) 1 d D U P A 2
F2C F 0.3067(9) 0.4048(10) 0.1839(8) 0.055(6) Uani 0.377(14) 1 d D U P A 2
C3C C 0.3064(11) 0.4245(17) 0.0654(8) 0.027(7) Uani 0.377(14) 1 d D U P A 2
H3C H 0.2464 0.4136 0.0469 0.032 Uiso 0.377(14) 1 calc R U P A 2
C4C C 0.3537(12) 0.4422(14) 0.0209(7) 0.024(6) Uani 0.377(14) 1 d D U P A 2
H4C H 0.3253 0.4454 -0.0293 0.029 Uiso 0.377(14) 1 calc R U P A 2
C5C C 0.4419(12) 0.4555(15) 0.0486(9) 0.023(6) Uani 0.377(14) 1 d D U P A 2
H5C H 0.4738 0.4638 0.0167 0.028 Uiso 0.377(14) 1 calc R U P A 2
C6C C 0.4844(11) 0.4568(19) 0.1221(9) 0.017(6) Uani 0.377(14) 1 d D U P A 2
H6C H 0.5438 0.4699 0.1408 0.020 Uiso 0.377(14) 1 calc R U P A 2
N7B N 0.4799(4) 0.4411(3) 0.2475(3) 0.0161(14) Uani 1 1 d . . . . .
C8B C 0.5001(5) 0.3819(4) 0.2840(4) 0.0186(17) Uani 1 1 d . U . . .
C81B C 0.4815(6) 0.3103(4) 0.2465(5) 0.028(2) Uani 1 1 d . . . . .
H81D H 0.4230 0.2947 0.2432 0.042 Uiso 1 1 calc R U . . .
H81E H 0.5238 0.2752 0.2738 0.042 Uiso 1 1 calc R U . . .
H81F H 0.4857 0.3148 0.1981 0.042 Uiso 1 1 calc R U . . .
C9B C 0.5364(5) 0.3777(4) 0.3597(5) 0.0220(18) Uani 1 1 d . . . . .
HB H 0.5613 0.3331 0.3784 0.026 Uiso 1 1 calc R U . . .
C10B C 0.5401(5) 0.4310(4) 0.4099(5) 0.0209(18) Uani 1 1 d . . . . .
O10B O 0.5177(3) 0.4960(3) 0.3971(3) 0.0199(12) Uani 1 1 d . . . . .
C11B C 0.5698(5) 0.4098(4) 0.4879(4) 0.0228(19) Uani 1 1 d . . . . .
H11D H 0.6311 0.4222 0.5098 0.034 Uiso 1 1 calc R U . . .
H11E H 0.5624 0.3583 0.4919 0.034 Uiso 1 1 calc R U . . .
H11F H 0.5353 0.4352 0.5127 0.034 Uiso 1 1 calc R U . . .
N12B N 0.6216(4) 0.5564(4) 0.3172(3) 0.0178(14) Uani 1 1 d . . . . .
C13B C 0.6751(5) 0.5126(5) 0.2971(5) 0.028(2) Uani 1 1 d . . . . .
H13B H 0.6511 0.4725 0.2679 0.034 Uiso 1 1 calc R U . . .
C14B C 0.7639(5) 0.5238(5) 0.3174(5) 0.033(2) Uani 1 1 d . . . . .
H14B H 0.7996 0.4920 0.3019 0.039 Uiso 1 1 calc R U . . .
C15B C 0.7994(5) 0.5807(5) 0.3597(5) 0.032(2) Uani 1 1 d . . . . .
H15B H 0.8602 0.5884 0.3741 0.038 Uiso 1 1 calc R U . . .
C16B C 0.7460(5) 0.6285(4) 0.3823(5) 0.0221(18) Uani 1 1 d . . . . .
C17B C 0.7760(6) 0.6889(5) 0.4289(5) 0.027(2) Uani 1 1 d . . . . .
H17B H 0.8362 0.6995 0.4468 0.033 Uiso 1 1 calc R U . . .
C18B C 0.7192(5) 0.7306(5) 0.4472(5) 0.026(2) Uani 1 1 d . . . . .
H18B H 0.7410 0.7699 0.4782 0.031 Uiso 1 1 calc R U . . .
C19B C 0.6278(5) 0.7185(4) 0.4224(4) 0.0209(18) Uani 1 1 d . . . . .
C20B C 0.5661(5) 0.7596(4) 0.4407(4) 0.0224(18) Uani 1 1 d . . . . .
H20B H 0.5839 0.7991 0.4722 0.027 Uiso 1 1 calc R U . . .
C21B C 0.4795(5) 0.7423(4) 0.4127(4) 0.0213(18) Uani 1 1 d . . . . .
H21B H 0.4385 0.7712 0.4248 0.026 Uiso 1 1 calc R U . . .
C22B C 0.4497(5) 0.6844(4) 0.3673(4) 0.0206(18) Uani 1 1 d . . . . .
H22B H 0.3893 0.6752 0.3488 0.025 Uiso 1 1 calc R U . . .
C23B C 0.5075(5) 0.6397(4) 0.3488(4) 0.0167(17) Uani 1 1 d . . . . .
C24B C 0.5961(5) 0.6593(4) 0.3764(4) 0.0180(17) Uani 1 1 d . . . . .
C25B C 0.6562(5) 0.6147(4) 0.3578(4) 0.0207(18) Uani 1 1 d . . . . .
N26B N 0.3593(4) 0.5471(3) 0.2706(3) 0.0165(14) Uani 1 1 d . . . . .
C27B C 0.3135(5) 0.5181(4) 0.3095(4) 0.0203(18) Uani 1 1 d . . . . .
H27B H 0.3437 0.4974 0.3547 0.024 Uiso 1 1 calc R U . . .
C28B C 0.2239(5) 0.5177(5) 0.2857(5) 0.028(2) Uani 1 1 d . . . . .
H28B H 0.1934 0.4962 0.3141 0.033 Uiso 1 1 calc R U . . .
C29B C 0.1786(5) 0.5486(5) 0.2207(5) 0.031(2) Uani 1 1 d . . . . .
H29B H 0.1171 0.5482 0.2039 0.037 Uiso 1 1 calc R U . . .
C30B C 0.2246(5) 0.5803(4) 0.1800(5) 0.0210(18) Uani 1 1 d . . . . .
C31B C 0.1851(5) 0.6131(5) 0.1109(5) 0.025(2) Uani 1 1 d . . . . .
H31B H 0.1238 0.6148 0.0910 0.030 Uiso 1 1 calc R U . . .
C32B C 0.2344(5) 0.6417(5) 0.0740(4) 0.025(2) Uani 1 1 d . . . . .
H32B H 0.2066 0.6630 0.0286 0.030 Uiso 1 1 calc R U . . .
C33B C 0.3281(5) 0.6407(4) 0.1017(5) 0.0233(19) Uani 1 1 d . . . . .
C34B C 0.3822(6) 0.6689(5) 0.0649(5) 0.026(2) Uani 1 1 d . . . . .
H34B H 0.3582 0.6915 0.0196 0.031 Uiso 1 1 calc R U . . .
C35B C 0.4714(6) 0.6627(5) 0.0965(5) 0.026(2) Uani 1 1 d . . . . .
H35B H 0.5081 0.6825 0.0725 0.032 Uiso 1 1 calc R U . . .
C36B C 0.5095(5) 0.6282(4) 0.1627(5) 0.0215(18) Uani 1 1 d . . . . .
H36B H 0.5708 0.6240 0.1814 0.026 Uiso 1 1 calc R U . . .
C37B C 0.4589(5) 0.6001(4) 0.2011(4) 0.0180(17) Uani 1 1 d . . . . .
C38B C 0.3679(5) 0.6076(4) 0.1683(4) 0.0178(17) Uani 1 1 d . . . . .
C39B C 0.3157(5) 0.5784(4) 0.2070(4) 0.0184(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1A C37A 1.996(8) . ?
Ir1A C23A 2.008(9) . ?
Ir1A N26A 2.042(7) . ?
Ir1A N12A 2.065(7) . ?
Ir1A O10A 2.133(6) . ?
Ir1A N7A 2.154(8) . ?
C1A C2A 1.383(11) . ?
C1A C6A 1.399(11) . ?
C1A N7A 1.442(10) . ?
C2A F2A 1.360(10) . ?
C2A C3A 1.378(12) . ?
C3A C4A 1.378(13) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.388(13) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.391(12) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A C8A 1.292(11) . ?
C8A C9A 1.441(13) . ?
C8A C81A 1.513(12) . ?
C81A H81A 0.9800 . ?
C81A H81B 0.9800 . ?
C81A H81C 0.9800 . ?
C9A C10A 1.370(13) . ?
C9A H9A 0.9500 . ?
C10A O10A 1.279(10) . ?
C10A C11A 1.516(12) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
N12A C13A 1.347(12) . ?
N12A C25A 1.358(12) . ?
C13A C14A 1.408(13) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.363(16) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.393(16) . ?
C15A H15A 0.9500 . ?
C16A C25A 1.419(13) . ?
C16A C17A 1.456(16) . ?
C17A C18A 1.354(17) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.408(14) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.406(15) . ?
C19A C24A 1.410(13) . ?
C20A C21A 1.354(15) . ?
C20A H20A 0.9500 . ?
C21A C22A 1.394(13) . ?
C21A H21A 0.9500 . ?
C22A C23A 1.377(13) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.434(12) . ?
C24A C25A 1.415(14) . ?
N26A C27A 1.346(11) . ?
N26A C39A 1.359(11) . ?
C27A C28A 1.397(12) . ?
C27A H27A 0.9500 . ?
C28A C29A 1.388(13) . ?
C28A H28A 0.9500 . ?
C29A C30A 1.402(13) . ?
C29A H29A 0.9500 . ?
C30A C39A 1.405(12) . ?
C30A C31A 1.419(13) . ?
C31A C32A 1.347(14) . ?
C31A H31A 0.9500 . ?
C32A C33A 1.442(13) . ?
C32A H32A 0.9500 . ?
C33A C34A 1.398(13) . ?
C33A C38A 1.415(12) . ?
C34A C35A 1.382(14) . ?
C34A H34A 0.9500 . ?
C35A C36A 1.419(13) . ?
C35A H35A 0.9500 . ?
C36A C37A 1.387(12) . ?
C36A H36A 0.9500 . ?
C37A C38A 1.431(12) . ?
C38A C39A 1.426(12) . ?
Ir1B C37B 2.006(8) . ?
Ir1B C23B 2.016(8) . ?
Ir1B N26B 2.037(6) . ?
Ir1B N12B 2.045(6) . ?
Ir1B O10B 2.152(6) . ?
Ir1B N7B 2.171(6) . ?
C1B C2B 1.382(12) . ?
C1B C6B 1.394(13) . ?
C1B N7B 1.404(11) . ?
C2B C3B 1.377(13) . ?
C2B F2B 1.378(11) . ?
C3B C4B 1.381(14) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.385(14) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.390(13) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C1C C2C 1.382(13) . ?
C1C C6C 1.394(13) . ?
C1C N7B 1.496(14) . ?
C2C F2C 1.370(11) . ?
C2C C3C 1.380(13) . ?
C3C C4C 1.381(14) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.386(14) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.390(14) . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
N7B C8B 1.306(10) . ?
C8B C9B 1.417(12) . ?
C8B C81B 1.515(11) . ?
C81B H81D 0.9800 . ?
C81B H81E 0.9800 . ?
C81B H81F 0.9800 . ?
C9B C10B 1.395(11) . ?
C9B HB 0.9500 . ?
C10B O10B 1.274(10) . ?
C10B C11B 1.508(11) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
N12B C13B 1.347(10) . ?
N12B C25B 1.365(10) . ?
C13B C14B 1.389(12) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.363(13) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.418(12) . ?
C15B H15B 0.9500 . ?
C16B C25B 1.411(11) . ?
C16B C17B 1.440(12) . ?
C17B C18B 1.346(12) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.428(11) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.404(11) . ?
C19B C24B 1.421(11) . ?
C20B C21B 1.378(12) . ?
C20B H20B 0.9500 . ?
C21B C22B 1.390(11) . ?
C21B H21B 0.9500 . ?
C22B C23B 1.395(11) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.418(11) . ?
C24B C25B 1.423(11) . ?
N26B C27B 1.346(10) . ?
N26B C39B 1.357(10) . ?
C27B C28B 1.383(11) . ?
C27B H27B 0.9500 . ?
C28B C29B 1.383(13) . ?
C28B H28B 0.9500 . ?
C29B C30B 1.396(12) . ?
C29B H29B 0.9500 . ?
C30B C39B 1.407(11) . ?
C30B C31B 1.442(12) . ?
C31B C32B 1.358(12) . ?
C31B H31B 0.9500 . ?
C32B C33B 1.446(11) . ?
C32B H32B 0.9500 . ?
C33B C34B 1.413(12) . ?
C33B C38B 1.407(11) . ?
C34B C35B 1.390(12) . ?
C34B H34B 0.9500 . ?
C35B C36B 1.409(12) . ?
C35B H35B 0.9500 . ?
C36B C37B 1.390(11) . ?
C36B H36B 0.9500 . ?
C37B C38B 1.421(11) . ?
C38B C39B 1.424(11) . ?

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
C37A Ir1A C23A 90.3(4) . . ?
C37A Ir1A N26A 81.7(3) . . ?
C23A Ir1A N26A 95.2(3) . . ?
C37A Ir1A N12A 96.3(3) . . ?
C23A Ir1A N12A 81.4(3) . . ?
N26A Ir1A N12A 176.2(3) . . ?
C37A Ir1A O10A 174.1(3) . . ?
C23A Ir1A O10A 86.9(3) . . ?
N26A Ir1A O10A 93.4(2) . . ?
N12A Ir1A O10A 88.4(2) . . ?
C37A Ir1A N7A 94.8(3) . . ?
C23A Ir1A N7A 173.3(3) . . ?
N26A Ir1A N7A 89.8(3) . . ?
N12A Ir1A N7A 93.7(3) . . ?
O10A Ir1A N7A 88.4(3) . . ?
C2A C1A C6A 117.7(8) . . ?
C2A C1A N7A 122.5(7) . . ?
C6A C1A N7A 119.8(8) . . ?
F2A C2A C3A 117.9(8) . . ?
F2A C2A C1A 117.3(8) . . ?
C3A C2A C1A 124.6(8) . . ?
C4A C3A C2A 116.9(9) . . ?
C4A C3A H3A 121.6 . . ?
C2A C3A H3A 121.6 . . ?
C3A C4A C5A 120.5(8) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C4A C5A C6A 121.8(9) . . ?
C4A C5A H5A 119.1 . . ?
C6A C5A H5A 119.1 . . ?
C5A C6A C1A 118.5(9) . . ?
C5A C6A H6A 120.8 . . ?
C1A C6A H6A 120.8 . . ?
C8A N7A C1A 118.3(8) . . ?
C8A N7A Ir1A 123.2(6) . . ?
C1A N7A Ir1A 118.4(6) . . ?
N7A C8A C9A 124.4(9) . . ?
N7A C8A C81A 120.6(9) . . ?
C9A C8A C81A 115.0(8) . . ?
C8A C81A H81A 109.5 . . ?
C8A C81A H81B 109.5 . . ?
H81A C81A H81B 109.5 . . ?
C8A C81A H81C 109.5 . . ?
H81A C81A H81C 109.5 . . ?
H81B C81A H81C 109.5 . . ?
C10A C9A C8A 127.7(8) . . ?
C10A C9A H9A 116.1 . . ?
C8A C9A H9A 116.1 . . ?
O10A C10A C9A 127.6(9) . . ?
O10A C10A C11A 113.9(8) . . ?
C9A C10A C11A 118.5(8) . . ?
C10A O10A Ir1A 122.6(6) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A N12A C25A 120.1(8) . . ?
C13A N12A Ir1A 126.7(6) . . ?
C25A N12A Ir1A 113.2(6) . . ?
N12A C13A C14A 119.6(10) . . ?
N12A C13A H13A 120.2 . . ?
C14A C13A H13A 120.2 . . ?
C15A C14A C13A 121.3(11) . . ?
C15A C14A H14A 119.3 . . ?
C13A C14A H14A 119.3 . . ?
C14A C15A C16A 119.4(9) . . ?
C14A C15A H15A 120.3 . . ?
C16A C15A H15A 120.3 . . ?
C15A C16A C25A 117.8(10) . . ?
C15A C16A C17A 125.9(10) . . ?
C25A C16A C17A 116.3(10) . . ?
C18A C17A C16A 121.2(10) . . ?
C18A C17A H17A 119.4 . . ?
C16A C17A H17A 119.4 . . ?
C17A C18A C19A 122.2(11) . . ?
C17A C18A H18A 118.9 . . ?
C19A C18A H18A 118.9 . . ?
C20A C19A C18A 124.3(10) . . ?
C20A C19A C24A 116.8(9) . . ?
C18A C19A C24A 118.8(11) . . ?
C21A C20A C19A 120.0(10) . . ?
C21A C20A H20A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C20A C21A C22A 122.1(10) . . ?
C20A C21A H21A 118.9 . . ?
C22A C21A H21A 118.9 . . ?
C23A C22A C21A 122.4(9) . . ?
C23A C22A H22A 118.8 . . ?
C21A C22A H22A 118.8 . . ?
C22A C23A C24A 114.5(9) . . ?
C22A C23A Ir1A 133.2(7) . . ?
C24A C23A Ir1A 112.2(7) . . ?
C19A C24A C25A 119.6(9) . . ?
C19A C24A C23A 124.2(9) . . ?
C25A C24A C23A 116.2(8) . . ?
N12A C25A C24A 116.6(8) . . ?
N12A C25A C16A 121.6(10) . . ?
C24A C25A C16A 121.8(9) . . ?
C27A N26A C39A 119.3(7) . . ?
C27A N26A Ir1A 126.6(6) . . ?
C39A N26A Ir1A 114.1(6) . . ?
N26A C27A C28A 121.3(9) . . ?
N26A C27A H27A 119.3 . . ?
C28A C27A H27A 119.3 . . ?
C29A C28A C27A 119.3(9) . . ?
C29A C28A H28A 120.3 . . ?
C27A C28A H28A 120.3 . . ?
C28A C29A C30A 120.3(8) . . ?
C28A C29A H29A 119.8 . . ?
C30A C29A H29A 119.8 . . ?
C29A C30A C39A 116.8(9) . . ?
C29A C30A C31A 125.4(9) . . ?
C39A C30A C31A 117.7(9) . . ?
C32A C31A C30A 121.1(9) . . ?
C32A C31A H31A 119.5 . . ?
C30A C31A H31A 119.5 . . ?
C31A C32A C33A 123.1(9) . . ?
C31A C32A H32A 118.5 . . ?
C33A C32A H32A 118.5 . . ?
C34A C33A C38A 118.1(8) . . ?
C34A C33A C32A 125.2(9) . . ?
C38A C33A C32A 116.7(9) . . ?
C35A C34A C33A 118.7(9) . . ?
C35A C34A H34A 120.6 . . ?
C33A C34A H34A 120.6 . . ?
C34A C35A C36A 122.9(9) . . ?
C34A C35A H35A 118.5 . . ?
C36A C35A H35A 118.5 . . ?
C37A C36A C35A 120.5(9) . . ?
C37A C36A H36A 119.8 . . ?
C35A C36A H36A 119.8 . . ?
C36A C37A C38A 115.7(8) . . ?
C36A C37A Ir1A 131.9(7) . . ?
C38A C37A Ir1A 112.4(6) . . ?
C33A C38A C39A 119.7(8) . . ?
C33A C38A C37A 124.0(8) . . ?
C39A C38A C37A 116.3(8) . . ?
N26A C39A C30A 122.8(8) . . ?
N26A C39A C38A 115.4(7) . . ?
C30A C39A C38A 121.8(8) . . ?
C37B Ir1B C23B 90.5(3) . . ?
C37B Ir1B N26B 81.3(3) . . ?
C23B Ir1B N26B 94.3(3) . . ?
C37B Ir1B N12B 95.7(3) . . ?
C23B Ir1B N12B 81.6(3) . . ?
N26B Ir1B N12B 174.9(3) . . ?
C37B Ir1B O10B 175.2(3) . . ?
C23B Ir1B O10B 86.0(3) . . ?
N26B Ir1B O10B 95.7(2) . . ?
N12B Ir1B O10B 87.1(2) . . ?
C37B Ir1B N7B 96.0(3) . . ?
C23B Ir1B N7B 173.4(3) . . ?
N26B Ir1B N7B 88.3(2) . . ?
N12B Ir1B N7B 96.1(2) . . ?
O10B Ir1B N7B 87.7(2) . . ?
C2B C1B C6B 118.3(8) . . ?
C2B C1B N7B 121.3(9) . . ?
C6B C1B N7B 120.4(9) . . ?
C3B C2B F2B 118.4(9) . . ?
C3B C2B C1B 124.1(9) . . ?
F2B C2B C1B 117.4(9) . . ?
C2B C3B C4B 116.7(10) . . ?
C2B C3B H3B 121.6 . . ?
C4B C3B H3B 121.6 . . ?
C3B C4B C5B 121.1(9) . . ?
C3B C4B H4B 119.4 . . ?
C5B C4B H4B 119.4 . . ?
C4B C5B C6B 121.0(10) . . ?
C4B C5B H5B 119.5 . . ?
C6B C5B H5B 119.5 . . ?
C5B C6B C1B 118.7(10) . . ?
C5B C6B H6B 120.6 . . ?
C1B C6B H6B 120.6 . . ?
C2C C1C C6C 118.3(9) . . ?
C2C C1C N7B 120.8(11) . . ?
C6C C1C N7B 120.7(11) . . ?
F2C C2C C3C 118.5(10) . . ?
F2C C2C C1C 117.3(10) . . ?
C3C C2C C1C 124.2(9) . . ?
C2C C3C C4C 116.6(10) . . ?
C2C C3C H3C 121.7 . . ?
C4C C3C H3C 121.7 . . ?
C3C C4C C5C 121.0(10) . . ?
C3C C4C H4C 119.5 . . ?
C5C C4C H4C 119.5 . . ?
C4C C5C C6C 121.2(10) . . ?
C4C C5C H5C 119.4 . . ?
C6C C5C H5C 119.4 . . ?
C5C C6C C1C 118.5(11) . . ?
C5C C6C H6C 120.7 . . ?
C1C C6C H6C 120.7 . . ?
C8B N7B C1B 117.7(10) . . ?
C8B N7B C1C 119.9(13) . . ?
C8B N7B Ir1B 124.8(5) . . ?
C1B N7B Ir1B 114.7(9) . . ?
C1C N7B Ir1B 115.1(13) . . ?
N7B C8B C9B 124.9(7) . . ?
N7B C8B C81B 120.6(7) . . ?
C9B C8B C81B 114.4(7) . . ?
C8B C81B H81D 109.5 . . ?
C8B C81B H81E 109.5 . . ?
H81D C81B H81E 109.5 . . ?
C8B C81B H81F 109.5 . . ?
H81D C81B H81F 109.5 . . ?
H81E C81B H81F 109.5 . . ?
C10B C9B C8B 127.9(8) . . ?
C10B C9B HB 116.1 . . ?
C8B C9B HB 116.1 . . ?
O10B C10B C9B 127.0(8) . . ?
O10B C10B C11B 115.5(7) . . ?
C9B C10B C11B 117.4(7) . . ?
C10B O10B Ir1B 124.7(5) . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13B N12B C25B 118.5(7) . . ?
C13B N12B Ir1B 127.7(6) . . ?
C25B N12B Ir1B 113.8(5) . . ?
N12B C13B C14B 122.5(9) . . ?
N12B C13B H13B 118.8 . . ?
C14B C13B H13B 118.8 . . ?
C15B C14B C13B 119.5(9) . . ?
C15B C14B H14B 120.2 . . ?
C13B C14B H14B 120.2 . . ?
C14B C15B C16B 120.3(8) . . ?
C14B C15B H15B 119.9 . . ?
C16B C15B H15B 119.9 . . ?
C25B C16B C15B 116.8(8) . . ?
C25B C16B C17B 117.6(8) . . ?
C15B C16B C17B 125.5(8) . . ?
C18B C17B C16B 120.4(8) . . ?
C18B C17B H17B 119.8 . . ?
C16B C17B H17B 119.8 . . ?
C17B C18B C19B 123.3(8) . . ?
C17B C18B H18B 118.4 . . ?
C19B C18B H18B 118.4 . . ?
C20B C19B C24B 116.7(7) . . ?
C20B C19B C18B 125.5(8) . . ?
C24B C19B C18B 117.8(8) . . ?
C21B C20B C19B 119.7(8) . . ?
C21B C20B H20B 120.2 . . ?
C19B C20B H20B 120.2 . . ?
C20B C21B C22B 122.8(8) . . ?
C20B C21B H21B 118.6 . . ?
C22B C21B H21B 118.6 . . ?
C21B C22B C23B 120.8(8) . . ?
C21B C22B H22B 119.6 . . ?
C23B C22B H22B 119.6 . . ?
C22B C23B C24B 115.8(7) . . ?
C22B C23B Ir1B 132.0(6) . . ?
C24B C23B Ir1B 112.1(6) . . ?
C23B C24B C19B 124.2(7) . . ?
C23B C24B C25B 116.8(7) . . ?
C19B C24B C25B 119.0(7) . . ?
N12B C25B C16B 122.3(7) . . ?
N12B C25B C24B 115.7(7) . . ?
C16B C25B C24B 121.9(8) . . ?
C27B N26B C39B 118.7(7) . . ?
C27B N26B Ir1B 127.1(5) . . ?
C39B N26B Ir1B 114.2(5) . . ?
N26B C27B C28B 121.9(8) . . ?
N26B C27B H27B 119.1 . . ?
C28B C27B H27B 119.1 . . ?
C29B C28B C27B 120.1(8) . . ?
C29B C28B H28B 119.9 . . ?
C27B C28B H28B 119.9 . . ?
C28B C29B C30B 119.0(8) . . ?
C28B C29B H29B 120.5 . . ?
C30B C29B H29B 120.5 . . ?
C29B C30B C39B 118.0(8) . . ?
C29B C30B C31B 124.4(8) . . ?
C39B C30B C31B 117.6(8) . . ?
C32B C31B C30B 120.9(7) . . ?
C32B C31B H31B 119.6 . . ?
C30B C31B H31B 119.6 . . ?
C31B C32B C33B 121.9(8) . . ?
C31B C32B H32B 119.1 . . ?
C33B C32B H32B 119.1 . . ?
C34B C33B C38B 117.9(8) . . ?
C34B C33B C32B 124.0(8) . . ?
C38B C33B C32B 118.1(8) . . ?
C35B C34B C33B 118.4(8) . . ?
C35B C34B H34B 120.8 . . ?
C33B C34B H34B 120.8 . . ?
C34B C35B C36B 122.5(8) . . ?
C34B C35B H35B 118.7 . . ?
C36B C35B H35B 118.7 . . ?
C37B C36B C35B 121.1(8) . . ?
C37B C36B H36B 119.4 . . ?
C35B C36B H36B 119.4 . . ?
C36B C37B C38B 115.5(8) . . ?
C36B C37B Ir1B 131.7(6) . . ?
C38B C37B Ir1B 112.8(6) . . ?
C33B C38B C37B 124.6(8) . . ?
C33B C38B C39B 119.6(7) . . ?
C37B C38B C39B 115.8(7) . . ?
N26B C39B C30B 122.3(8) . . ?
N26B C39B C38B 115.8(7) . . ?
C30B C39B C38B 121.9(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
C6A C1A C2A F2A -179.4(8) . . . . ?
N7A C1A C2A F2A 2.5(14) . . . . ?
C6A C1A C2A C3A -2.8(15) . . . . ?
N7A C1A C2A C3A 179.1(9) . . . . ?
F2A C2A C3A C4A 179.0(9) . . . . ?
C1A C2A C3A C4A 2.4(16) . . . . ?
C2A C3A C4A C5A -0.6(16) . . . . ?
C3A C4A C5A C6A -0.6(17) . . . . ?
C4A C5A C6A C1A 0.2(15) . . . . ?
C2A C1A C6A C5A 1.4(14) . . . . ?
N7A C1A C6A C5A 179.5(8) . . . . ?
C2A C1A N7A C8A -94.8(11) . . . . ?
C6A C1A N7A C8A 87.2(10) . . . . ?
C2A C1A N7A Ir1A 88.9(9) . . . . ?
C6A C1A N7A Ir1A -89.2(9) . . . . ?
C1A N7A C8A C9A -167.1(8) . . . . ?
Ir1A N7A C8A C9A 9.1(11) . . . . ?
C1A N7A C8A C81A 12.7(12) . . . . ?
Ir1A N7A C8A C81A -171.1(6) . . . . ?
N7A C8A C9A C10A 13.4(14) . . . . ?
C81A C8A C9A C10A -166.4(8) . . . . ?
C8A C9A C10A O10A -12.9(14) . . . . ?
C8A C9A C10A C11A 165.6(8) . . . . ?
C9A C10A O10A Ir1A -10.3(11) . . . . ?
C11A C10A O10A Ir1A 171.1(5) . . . . ?
C25A N12A C13A C14A 1.9(13) . . . . ?
Ir1A N12A C13A C14A -179.1(7) . . . . ?
N12A C13A C14A C15A -0.2(15) . . . . ?
C13A C14A C15A C16A -0.2(16) . . . . ?
C14A C15A C16A C25A -1.0(15) . . . . ?
C14A C15A C16A C17A 179.5(10) . . . . ?
C15A C16A C17A C18A 178.0(10) . . . . ?
C25A C16A C17A C18A -1.5(14) . . . . ?
C16A C17A C18A C19A -2.1(16) . . . . ?
C17A C18A C19A C20A -174.5(10) . . . . ?
C17A C18A C19A C24A 4.4(15) . . . . ?
C18A C19A C20A C21A 179.5(10) . . . . ?
C24A C19A C20A C21A 0.6(14) . . . . ?
C19A C20A C21A C22A 1.8(16) . . . . ?
C20A C21A C22A C23A -2.9(16) . . . . ?
C21A C22A C23A C24A 1.3(13) . . . . ?
C21A C22A C23A Ir1A 178.0(8) . . . . ?
C20A C19A C24A C25A 176.0(8) . . . . ?
C18A C19A C24A C25A -3.1(13) . . . . ?
C20A C19A C24A C23A -2.1(14) . . . . ?
C18A C19A C24A C23A 178.9(9) . . . . ?
C22A C23A C24A C19A 1.1(13) . . . . ?
Ir1A C23A C24A C19A -176.2(7) . . . . ?
C22A C23A C24A C25A -177.0(8) . . . . ?
Ir1A C23A C24A C25A 5.6(10) . . . . ?
C13A N12A C25A C24A 176.3(8) . . . . ?
Ir1A N12A C25A C24A -2.8(10) . . . . ?
C13A N12A C25A C16A -3.2(13) . . . . ?
Ir1A N12A C25A C16A 177.6(7) . . . . ?
C19A C24A C25A N12A 180.0(8) . . . . ?
C23A C24A C25A N12A -1.8(12) . . . . ?
C19A C24A C25A C16A -0.5(13) . . . . ?
C23A C24A C25A C16A 177.7(8) . . . . ?
C15A C16A C25A N12A 2.8(14) . . . . ?
C17A C16A C25A N12A -177.7(8) . . . . ?
C15A C16A C25A C24A -176.8(9) . . . . ?
C17A C16A C25A C24A 2.8(13) . . . . ?
C39A N26A C27A C28A 2.1(13) . . . . ?
Ir1A N26A C27A C28A -176.9(7) . . . . ?
N26A C27A C28A C29A -0.7(14) . . . . ?
C27A C28A C29A C30A -1.0(14) . . . . ?
C28A C29A C30A C39A 1.3(13) . . . . ?
C28A C29A C30A C31A -179.9(9) . . . . ?
C29A C30A C31A C32A -178.8(9) . . . . ?
C39A C30A C31A C32A -0.1(14) . . . . ?
C30A C31A C32A C33A -1.0(15) . . . . ?
C31A C32A C33A C34A -178.2(9) . . . . ?
C31A C32A C33A C38A 1.6(14) . . . . ?
C38A C33A C34A C35A -1.0(13) . . . . ?
C32A C33A C34A C35A 178.8(9) . . . . ?
C33A C34A C35A C36A 2.4(13) . . . . ?
C34A C35A C36A C37A -0.7(14) . . . . ?
C35A C36A C37A C38A -2.2(12) . . . . ?
C35A C36A C37A Ir1A 179.2(7) . . . . ?
C34A C33A C38A C39A 178.7(8) . . . . ?
C32A C33A C38A C39A -1.1(12) . . . . ?
C34A C33A C38A C37A -2.1(13) . . . . ?
C32A C33A C38A C37A 178.1(8) . . . . ?
C36A C37A C38A C33A 3.7(13) . . . . ?
Ir1A C37A C38A C33A -177.5(7) . . . . ?
C36A C37A C38A C39A -177.1(8) . . . . ?
Ir1A C37A C38A C39A 1.8(10) . . . . ?
C27A N26A C39A C30A -1.8(13) . . . . ?
Ir1A N26A C39A C30A 177.3(7) . . . . ?
C27A N26A C39A C38A 178.9(8) . . . . ?
Ir1A N26A C39A C38A -2.0(9) . . . . ?
C29A C30A C39A N26A 0.1(13) . . . . ?
C31A C30A C39A N26A -178.8(8) . . . . ?
C29A C30A C39A C38A 179.4(8) . . . . ?
C31A C30A C39A C38A 0.5(13) . . . . ?
C33A C38A C39A N26A 179.5(7) . . . . ?
C37A C38A C39A N26A 0.2(11) . . . . ?
C33A C38A C39A C30A 0.1(13) . . . . ?
C37A C38A C39A C30A -179.2(8) . . . . ?
C6B C1B C2B C3B 0(3) . . . . ?
N7B C1B C2B C3B -177.1(17) . . . . ?
C6B C1B C2B F2B -175.7(17) . . . . ?
N7B C1B C2B F2B 7(3) . . . . ?
F2B C2B C3B C4B 175.9(16) . . . . ?
C1B C2B C3B C4B 0(3) . . . . ?
C2B C3B C4B C5B 1(3) . . . . ?
C3B C4B C5B C6B -2(3) . . . . ?
C4B C5B C6B C1B 2(3) . . . . ?
C2B C1B C6B C5B -1(3) . . . . ?
N7B C1B C6B C5B 175.9(16) . . . . ?
C6C C1C C2C F2C 179(3) . . . . ?
N7B C1C C2C F2C -6(4) . . . . ?
C6C C1C C2C C3C 1(5) . . . . ?
N7B C1C C2C C3C 176(3) . . . . ?
F2C C2C C3C C4C -179(3) . . . . ?
C1C C2C C3C C4C -1(5) . . . . ?
C2C C3C C4C C5C 2(5) . . . . ?
C3C C4C C5C C6C -5(5) . . . . ?
C4C C5C C6C C1C 5(5) . . . . ?
C2C C1C C6C C5C -4(5) . . . . ?
N7B C1C C6C C5C -178(3) . . . . ?
C2B C1B N7B C8B -112.7(17) . . . . ?
C6B C1B N7B C8B 70(2) . . . . ?
C2B C1B N7B C1C -9(8) . . . . ?
C6B C1B N7B C1C 174(10) . . . . ?
C2B C1B N7B Ir1B 85.4(18) . . . . ?
C6B C1B N7B Ir1B -91.8(18) . . . . ?
C2C C1C N7B C8B 78(3) . . . . ?
C6C C1C N7B C8B -107(3) . . . . ?
C2C C1C N7B C1B -5(7) . . . . ?
C6C C1C N7B C1B 170(11) . . . . ?
C2C C1C N7B Ir1B -96(3) . . . . ?
C6C C1C N7B Ir1B 79(3) . . . . ?
C1B N7B C8B C9B -163.5(9) . . . . ?
C1C N7B C8B C9B -177.2(9) . . . . ?
Ir1B N7B C8B C9B -3.6(11) . . . . ?
C1B N7B C8B C81B 13.6(12) . . . . ?
C1C N7B C8B C81B 0.0(13) . . . . ?
Ir1B N7B C8B C81B 173.6(6) . . . . ?
N7B C8B C9B C10B 15.3(14) . . . . ?
C81B C8B C9B C10B -162.0(8) . . . . ?
C8B C9B C10B O10B -6.3(14) . . . . ?
C8B C9B C10B C11B 170.8(8) . . . . ?
C9B C10B O10B Ir1B -12.5(11) . . . . ?
C11B C10B O10B Ir1B 170.5(5) . . . . ?
C25B N12B C13B C14B 1.5(13) . . . . ?
Ir1B N12B C13B C14B -178.5(7) . . . . ?
N12B C13B C14B C15B 0.5(15) . . . . ?
C13B C14B C15B C16B -0.6(15) . . . . ?
C14B C15B C16B C25B -1.3(13) . . . . ?
C14B C15B C16B C17B 177.7(9) . . . . ?
C25B C16B C17B C18B -0.6(13) . . . . ?
C15B C16B C17B C18B -179.6(9) . . . . ?
C16B C17B C18B C19B -0.2(14) . . . . ?
C17B C18B C19B C20B 179.0(8) . . . . ?
C17B C18B C19B C24B 0.3(13) . . . . ?
C24B C19B C20B C21B -1.5(12) . . . . ?
C18B C19B C20B C21B 179.8(8) . . . . ?
C19B C20B C21B C22B 1.2(13) . . . . ?
C20B C21B C22B C23B 1.1(13) . . . . ?
C21B C22B C23B C24B -2.8(11) . . . . ?
C21B C22B C23B Ir1B 172.7(6) . . . . ?
C22B C23B C24B C19B 2.5(12) . . . . ?
Ir1B C23B C24B C19B -173.9(6) . . . . ?
C22B C23B C24B C25B -179.6(7) . . . . ?
Ir1B C23B C24B C25B 4.0(9) . . . . ?
C20B C19B C24B C23B -0.4(12) . . . . ?
C18B C19B C24B C23B 178.5(8) . . . . ?
C20B C19B C24B C25B -178.3(7) . . . . ?
C18B C19B C24B C25B 0.6(12) . . . . ?
C13B N12B C25B C16B -3.4(12) . . . . ?
Ir1B N12B C25B C16B 176.5(6) . . . . ?
C13B N12B C25B C24B 179.2(7) . . . . ?
Ir1B N12B C25B C24B -0.9(9) . . . . ?
C15B C16B C25B N12B 3.3(13) . . . . ?
C17B C16B C25B N12B -175.8(8) . . . . ?
C15B C16B C25B C24B -179.5(8) . . . . ?
C17B C16B C25B C24B 1.5(13) . . . . ?
C23B C24B C25B N12B -2.1(11) . . . . ?
C19B C24B C25B N12B 175.9(7) . . . . ?
C23B C24B C25B C16B -179.5(8) . . . . ?
C19B C24B C25B C16B -1.5(12) . . . . ?
C39B N26B C27B C28B 1.9(12) . . . . ?
Ir1B N26B C27B C28B -175.9(6) . . . . ?
N26B C27B C28B C29B -1.0(14) . . . . ?
C27B C28B C29B C30B -0.4(14) . . . . ?
C28B C29B C30B C39B 0.9(13) . . . . ?
C28B C29B C30B C31B 179.0(8) . . . . ?
C29B C30B C31B C32B -178.7(8) . . . . ?
C39B C30B C31B C32B -0.7(12) . . . . ?
C30B C31B C32B C33B 0.0(13) . . . . ?
C31B C32B C33B C34B 179.1(8) . . . . ?
C31B C32B C33B C38B 1.3(13) . . . . ?
C38B C33B C34B C35B -0.3(12) . . . . ?
C32B C33B C34B C35B -178.1(8) . . . . ?
C33B C34B C35B C36B 1.4(13) . . . . ?
C34B C35B C36B C37B -2.0(13) . . . . ?
C35B C36B C37B C38B 1.3(12) . . . . ?
C35B C36B C37B Ir1B 178.6(6) . . . . ?
C34B C33B C38B C37B -0.3(13) . . . . ?
C32B C33B C38B C37B 177.6(8) . . . . ?
C34B C33B C38B C39B -179.8(7) . . . . ?
C32B C33B C38B C39B -1.9(12) . . . . ?
C36B C37B C38B C33B -0.2(12) . . . . ?
Ir1B C37B C38B C33B -178.0(6) . . . . ?
C36B C37B C38B C39B 179.4(7) . . . . ?
Ir1B C37B C38B C39B 1.6(9) . . . . ?
C27B N26B C39B C30B -1.3(11) . . . . ?
Ir1B N26B C39B C30B 176.7(6) . . . . ?
C27B N26B C39B C38B -179.7(7) . . . . ?
Ir1B N26B C39B C38B -1.6(9) . . . . ?
C29B C30B C39B N26B 0.0(12) . . . . ?
C31B C30B C39B N26B -178.2(7) . . . . ?
C29B C30B C39B C38B 178.2(8) . . . . ?
C31B C30B C39B C38B 0.0(12) . . . . ?
C33B C38B C39B N26B 179.6(7) . . . . ?
C37B C38B C39B N26B 0.1(11) . . . . ?
C33B C38B C39B C30B 1.3(12) . . . . ?
C37B C38B C39B C30B -178.3(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13A H13A F2A 0.95 2.45 3.196(13) 135.1 .
C13A H13A N7A 0.95 2.67 3.205(12) 116.2 .
C27A H27A O10A 0.95 2.59 3.150(10) 118.1 .
C11B H11F O10B 0.98 2.56 3.518(10) 165.4 3_666

_refine_diff_density_max         2.871
_refine_diff_density_min         -1.808
_refine_diff_density_rms         0.199

_shelxl_version_number           2013-4



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1814940'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H27 F3 Ir N3 O, 0.5(C H4 O)'
_chemical_formula_sum            'C38.50 H29 F3 Ir N3 O1.50'
_chemical_formula_weight         806.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.6629(10)
_cell_length_b                   9.1355(2)
_cell_length_c                   29.0965(11)
_cell_angle_alpha                90
_cell_angle_beta                 117.344(5)
_cell_angle_gamma                90
_cell_volume                     6531.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    6785
_cell_measurement_theta_min      3.6000
_cell_measurement_theta_max      26.7940

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             3176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    4.143
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            14409
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.057
_diffrn_reflns_theta_max         27.010
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6545
_reflns_number_gt                5874
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²+3.6054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6545
_refine_ls_number_parameters     473
_refine_ls_number_restraints     204
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.32923(2) 0.57618(2) 0.42425(2) 0.02002(9) Uani 1 1 d . . . . .
C1 C 0.43500(18) 0.6999(6) 0.43174(18) 0.0268(10) Uani 1 1 d . U . . .
C2 C 0.4300(2) 0.8364(7) 0.4095(2) 0.0433(14) Uani 1 1 d . U . . .
H2 H 0.4146 0.9160 0.4193 0.052 Uiso 1 1 calc R U . . .
C3 C 0.4485(3) 0.8550(10) 0.3715(3) 0.0623(18) Uani 1 1 d . U . . .
H3 H 0.4453 0.9479 0.3557 0.075 Uiso 1 1 calc R U . . .
C4 C 0.4704(3) 0.7416(11) 0.3579(3) 0.0690(19) Uani 1 1 d . U . . .
C41 C 0.49392(19) 0.7563(6) 0.3178(2) 0.085(3) Uani 0.654(8) 1 d D U P A 1
F41A F 0.5185(3) 0.8882(6) 0.3257(3) 0.084(3) Uani 0.654(8) 1 d D U P A 1
F41B F 0.5296(2) 0.6496(6) 0.3224(2) 0.076(2) Uani 0.654(8) 1 d D U P A 1
F41C F 0.4509(2) 0.7520(11) 0.2702(3) 0.121(4) Uani 0.654(8) 1 d D U P A 1
C41A C 0.4789(5) 0.8030(13) 0.3098(4) 0.100(6) Uani 0.346(8) 1 d D U P A 2
F41D F 0.4653(8) 0.6822(12) 0.2797(7) 0.113(6) Uani 0.346(8) 1 d D U P A 2
F41E F 0.5322(4) 0.833(2) 0.3272(9) 0.140(8) Uani 0.346(8) 1 d D U P A 2
F41F F 0.4486(5) 0.9178(12) 0.2826(6) 0.095(5) Uani 0.346(8) 1 d D U P A 2
C5 C 0.4761(3) 0.6106(10) 0.3800(3) 0.0610(17) Uani 1 1 d . U . . .
H5 H 0.4921 0.5328 0.3700 0.073 Uiso 1 1 calc R U . . .
C6 C 0.4592(2) 0.5867(7) 0.4171(2) 0.0419(14) Uani 1 1 d . U . . .
H6 H 0.4639 0.4931 0.4329 0.050 Uiso 1 1 calc R U . . .
N7 N 0.41036(15) 0.6696(4) 0.46449(14) 0.0196(8) Uani 1 1 d . . . . .
C8 C 0.43156(19) 0.7274(5) 0.51111(18) 0.0237(10) Uani 1 1 d . . . . .
C81 C 0.4877(2) 0.7987(6) 0.5344(2) 0.0314(11) Uani 1 1 d . . . . .
H81A H 0.5092 0.7554 0.5189 0.047 Uiso 1 1 calc R U . . .
H81B H 0.5061 0.7824 0.5719 0.047 Uiso 1 1 calc R U . . .
H81C H 0.4837 0.9041 0.5273 0.047 Uiso 1 1 calc R U . . .
C9 C 0.4044(2) 0.7315(5) 0.54215(19) 0.0275(10) Uani 1 1 d . . . . .
H9 H 0.4268 0.7510 0.5778 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3499(2) 0.7113(5) 0.52774(19) 0.0253(10) Uani 1 1 d . . . . .
O10 O 0.31341(13) 0.6712(3) 0.48338(13) 0.0251(7) Uani 1 1 d . . . . .
C11 C 0.3297(2) 0.7473(5) 0.5664(2) 0.0315(12) Uani 1 1 d . . . . .
H11A H 0.2920 0.7818 0.5482 0.047 Uiso 1 1 calc R U . . .
H11B H 0.3525 0.8240 0.5899 0.047 Uiso 1 1 calc R U . . .
H11C H 0.3313 0.6595 0.5865 0.047 Uiso 1 1 calc R U . . .
N12 N 0.34689(16) 0.3850(4) 0.46556(15) 0.0207(8) Uani 1 1 d . . . . .
C13 C 0.3948(2) 0.3375(5) 0.50071(19) 0.0283(11) Uani 1 1 d . . . . .
H13 H 0.4258 0.3971 0.5090 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4018(2) 0.2030(6) 0.5263(2) 0.0343(12) Uani 1 1 d . . . . .
H14 H 0.4371 0.1709 0.5504 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3570(2) 0.1185(6) 0.5161(2) 0.0345(12) Uani 1 1 d . . . . .
H15 H 0.3611 0.0278 0.5335 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3055(2) 0.1655(5) 0.4802(2) 0.0313(12) Uani 1 1 d . . . . .
C17 C 0.2555(3) 0.0906(5) 0.4675(3) 0.0394(14) Uani 1 1 d . . . . .
H17 H 0.2562 0.0021 0.4850 0.047 Uiso 1 1 calc R U . . .
C18 C 0.2077(2) 0.1429(6) 0.4315(2) 0.0400(14) Uani 1 1 d . . . . .
H18 H 0.1755 0.0894 0.4240 0.048 Uiso 1 1 calc R U . . .
C19 C 0.2032(2) 0.2788(6) 0.4034(2) 0.0328(12) Uani 1 1 d . . . . .
C20 C 0.1546(2) 0.3382(6) 0.3650(2) 0.0393(13) Uani 1 1 d . . . . .
H20 H 0.1211 0.2889 0.3554 0.047 Uiso 1 1 calc R U . . .
C21 C 0.1553(2) 0.4661(7) 0.3414(2) 0.0361(13) Uani 1 1 d . . . . .
H21 H 0.1222 0.5042 0.3152 0.043 Uiso 1 1 calc R U . . .
C22 C 0.2043(2) 0.5442(6) 0.3550(2) 0.0276(11) Uani 1 1 d . . . . .
H22 H 0.2033 0.6339 0.3381 0.033 Uiso 1 1 calc R U . . .
C23 C 0.25365(19) 0.4916(5) 0.39257(18) 0.0232(10) Uani 1 1 d . . . . .
C24 C 0.2521(2) 0.3550(5) 0.41643(18) 0.0261(10) Uani 1 1 d . . . . .
C25 C 0.3020(2) 0.2999(5) 0.45471(18) 0.0241(10) Uani 1 1 d . . . . .
N26 N 0.30711(15) 0.7569(4) 0.37823(15) 0.0243(8) Uani 1 1 d . . . . .
C27 C 0.2915(2) 0.8859(5) 0.3874(2) 0.0285(11) Uani 1 1 d . . . . .
H27 H 0.2869 0.8972 0.4176 0.034 Uiso 1 1 calc R U . . .
C28 C 0.2816(2) 1.0040(6) 0.3553(2) 0.0365(12) Uani 1 1 d . . . . .
H28 H 0.2713 1.0951 0.3638 0.044 Uiso 1 1 calc R U . . .
C29 C 0.2868(2) 0.9904(6) 0.3102(2) 0.0375(13) Uani 1 1 d . . . . .
H29 H 0.2803 1.0720 0.2879 0.045 Uiso 1 1 calc R U . . .
C30 C 0.30159(19) 0.8548(6) 0.29807(19) 0.0291(11) Uani 1 1 d . . . . .
C31 C 0.3097(2) 0.8249(7) 0.2540(2) 0.0378(13) Uani 1 1 d . . . . .
H31 H 0.3029 0.9001 0.2292 0.045 Uiso 1 1 calc R U . . .
C32 C 0.3269(2) 0.6917(6) 0.24651(19) 0.0352(12) Uani 1 1 d . . . . .
H32 H 0.3319 0.6765 0.2167 0.042 Uiso 1 1 calc R U . . .
C33 C 0.3376(2) 0.5735(5) 0.2823(2) 0.0302(12) Uani 1 1 d . . . . .
C34 C 0.3548(2) 0.4343(6) 0.2770(2) 0.0352(13) Uani 1 1 d . . . . .
H34 H 0.3611 0.4125 0.2483 0.042 Uiso 1 1 calc R U . . .
C35 C 0.3629(2) 0.3278(6) 0.3135(2) 0.0351(12) Uani 1 1 d . . . . .
H35 H 0.3734 0.2324 0.3086 0.042 Uiso 1 1 calc R U . . .
C36 C 0.3560(2) 0.3563(5) 0.3575(2) 0.0282(11) Uani 1 1 d . . . . .
H36 H 0.3627 0.2804 0.3820 0.034 Uiso 1 1 calc R U . . .
C37 C 0.33959(17) 0.4938(5) 0.36600(17) 0.0204(9) Uani 1 1 d . . . . .
C38 C 0.32924(19) 0.5989(5) 0.32602(19) 0.0238(10) Uani 1 1 d . . . . .
C39 C 0.31146(18) 0.7400(5) 0.33299(18) 0.0239(10) Uani 1 1 d . . . . .
C1A C 0.5513(7) 0.301(2) 0.3022(6) 0.076(5) Uani 0.5 1 d . . P . .
H1A1 H 0.5587 0.3954 0.3201 0.115 Uiso 0.5 1 calc R U P . .
H1A2 H 0.5485 0.3143 0.2676 0.115 Uiso 0.5 1 calc R U P . .
H1A3 H 0.5810 0.2327 0.3220 0.115 Uiso 0.5 1 calc R U P . .
O1A O 0.5002(8) 0.2415(14) 0.2975(5) 0.128(7) Uani 0.5 1 d . . P . .
H1A H 0.4942 0.1598 0.2827 0.153 Uiso 0.5 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C37 1.992(4) . ?
Ir1 C23 2.012(5) . ?
Ir1 N26 2.035(4) . ?
Ir1 N12 2.048(4) . ?
Ir1 O10 2.144(3) . ?
Ir1 N7 2.173(4) . ?
C1 C2 1.382(7) . ?
C1 C6 1.399(7) . ?
C1 N7 1.430(5) . ?
C2 C3 1.425(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.348(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.332(11) . ?
C4 C41 1.582(8) . ?
C4 C41A 1.623(14) . ?
C41 F41C 1.3499(10) . ?
C41 F41B 1.3500(10) . ?
C41 F41A 1.3503(10) . ?
C41A F41E 1.3498(11) . ?
C41A F41F 1.3499(10) . ?
C41A F41D 1.3501(10) . ?
C5 C6 1.380(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.316(6) . ?
C8 C9 1.416(6) . ?
C8 C81 1.525(7) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C9 C10 1.379(7) . ?
C9 H9 0.9500 . ?
C10 O10 1.274(6) . ?
C10 C11 1.507(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N12 C13 1.321(6) . ?
N12 C25 1.374(6) . ?
C13 C14 1.404(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(8) . ?
C15 H15 0.9500 . ?
C16 C25 1.414(7) . ?
C16 C17 1.431(7) . ?
C17 C18 1.342(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.460(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.404(8) . ?
C19 C24 1.409(7) . ?
C20 C21 1.360(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.417(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.439(7) . ?
C24 C25 1.410(7) . ?
N26 C27 1.324(6) . ?
N26 C39 1.384(6) . ?
C27 C28 1.370(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.388(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.399(8) . ?
C29 H29 0.9500 . ?
C30 C39 1.398(7) . ?
C30 C31 1.426(7) . ?
C31 C32 1.360(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.433(7) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(7) . ?
C33 C38 1.413(7) . ?
C34 C35 1.380(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.403(7) . ?
C35 H35 0.9500 . ?
C36 C37 1.396(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.432(7) . ?
C38 C39 1.426(7) . ?
C1A O1A 1.46(2) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?
O1A H1A 0.8400 . ?

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
C37 Ir1 C23 89.46(17) . . ?
C37 Ir1 N26 82.17(17) . . ?
C23 Ir1 N26 94.29(18) . . ?
C37 Ir1 N12 95.07(16) . . ?
C23 Ir1 N12 81.90(18) . . ?
N26 Ir1 N12 175.34(15) . . ?
C37 Ir1 O10 176.37(15) . . ?
C23 Ir1 O10 88.34(15) . . ?
N26 Ir1 O10 95.12(14) . . ?
N12 Ir1 O10 87.48(13) . . ?
C37 Ir1 N7 95.17(15) . . ?
C23 Ir1 N7 175.18(15) . . ?
N26 Ir1 N7 87.71(14) . . ?
N12 Ir1 N7 96.30(14) . . ?
O10 Ir1 N7 87.11(13) . . ?
C2 C1 C6 118.9(5) . . ?
C2 C1 N7 120.7(5) . . ?
C6 C1 N7 120.0(5) . . ?
C1 C2 C3 118.5(6) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 120.3(7) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 121.4(7) . . ?
C5 C4 C41 115.6(7) . . ?
C3 C4 C41 122.9(7) . . ?
C5 C4 C41A 133.8(8) . . ?
C3 C4 C41A 104.5(8) . . ?
F41C C41 F41B 109.84(17) . . ?
F41C C41 F41A 109.77(18) . . ?
F41B C41 F41A 109.85(18) . . ?
F41C C41 C4 106.7(5) . . ?
F41B C41 C4 113.3(5) . . ?
F41A C41 C4 107.3(5) . . ?
F41E C41A F41F 109.86(18) . . ?
F41E C41A F41D 109.89(18) . . ?
F41F C41A F41D 109.99(18) . . ?
F41E C41A C4 108.2(11) . . ?
F41F C41A C4 118.5(10) . . ?
F41D C41A C4 99.8(11) . . ?
C4 C5 C6 120.7(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.2(6) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 N7 C1 119.1(4) . . ?
C8 N7 Ir1 125.0(3) . . ?
C1 N7 Ir1 114.0(3) . . ?
N7 C8 C9 123.5(4) . . ?
N7 C8 C81 120.7(4) . . ?
C9 C8 C81 115.8(4) . . ?
C8 C81 H81A 109.5 . . ?
C8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C10 C9 C8 128.9(5) . . ?
C10 C9 H9 115.5 . . ?
C8 C9 H9 115.5 . . ?
O10 C10 C9 126.4(4) . . ?
O10 C10 C11 115.2(4) . . ?
C9 C10 C11 118.2(4) . . ?
C10 O10 Ir1 124.8(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 N12 C25 118.1(4) . . ?
C13 N12 Ir1 128.2(3) . . ?
C25 N12 Ir1 113.6(3) . . ?
N12 C13 C14 122.9(5) . . ?
N12 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C15 C14 C13 119.1(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.0(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C25 117.4(5) . . ?
C15 C16 C17 125.5(5) . . ?
C25 C16 C17 117.1(5) . . ?
C18 C17 C16 121.2(5) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 122.8(5) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 C19 C24 118.2(5) . . ?
C20 C19 C18 125.4(5) . . ?
C24 C19 C18 116.3(5) . . ?
C21 C20 C19 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.7(5) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 121.0(5) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 116.3(4) . . ?
C22 C23 Ir1 132.0(4) . . ?
C24 C23 Ir1 111.6(3) . . ?
C19 C24 C25 120.5(5) . . ?
C19 C24 C23 122.5(5) . . ?
C25 C24 C23 117.1(4) . . ?
N12 C25 C24 115.7(4) . . ?
N12 C25 C16 122.3(5) . . ?
C24 C25 C16 122.0(4) . . ?
C27 N26 C39 118.0(4) . . ?
C27 N26 Ir1 128.1(3) . . ?
C39 N26 Ir1 113.8(3) . . ?
N26 C27 C28 123.1(5) . . ?
N26 C27 H27 118.5 . . ?
C28 C27 H27 118.5 . . ?
C27 C28 C29 119.9(5) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C30 119.1(5) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C39 C30 C29 117.6(5) . . ?
C39 C30 C31 116.8(5) . . ?
C29 C30 C31 125.5(5) . . ?
C32 C31 C30 121.7(5) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C31 C32 C33 121.9(5) . . ?
C31 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
C34 C33 C38 117.1(5) . . ?
C34 C33 C32 125.1(5) . . ?
C38 C33 C32 117.7(5) . . ?
C35 C34 C33 120.1(5) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 122.0(5) . . ?
C34 C35 H35 119.0 . . ?
C36 C35 H35 119.0 . . ?
C37 C36 C35 121.3(5) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C36 C37 C38 114.8(4) . . ?
C36 C37 Ir1 132.6(4) . . ?
C38 C37 Ir1 112.6(3) . . ?
C33 C38 C39 119.1(5) . . ?
C33 C38 C37 124.5(5) . . ?
C39 C38 C37 116.3(4) . . ?
N26 C39 C30 122.3(4) . . ?
N26 C39 C38 115.0(4) . . ?
C30 C39 C38 122.7(5) . . ?
O1A C1A H1A1 109.5 . . ?
O1A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
O1A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
C1A O1A H1A 109.5 . . ?

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
C6 C1 C2 C3 1.6(8) . . . . ?
N7 C1 C2 C3 -171.1(5) . . . . ?
C1 C2 C3 C4 -0.2(9) . . . . ?
C2 C3 C4 C5 -1.1(11) . . . . ?
C2 C3 C4 C41 -177.3(5) . . . . ?
C2 C3 C4 C41A 173.4(6) . . . . ?
C5 C4 C41 F41C 103.2(6) . . . . ?
C3 C4 C41 F41C -80.3(7) . . . . ?
C5 C4 C41 F41B -17.8(8) . . . . ?
C3 C4 C41 F41B 158.7(6) . . . . ?
C5 C4 C41 F41A -139.2(6) . . . . ?
C3 C4 C41 F41A 37.3(8) . . . . ?
C5 C4 C41A F41E -83.0(11) . . . . ?
C3 C4 C41A F41E 103.6(9) . . . . ?
C5 C4 C41A F41F 151.1(10) . . . . ?
C3 C4 C41A F41F -22.3(11) . . . . ?
C5 C4 C41A F41D 31.9(11) . . . . ?
C3 C4 C41A F41D -141.6(8) . . . . ?
C3 C4 C5 C6 0.8(11) . . . . ?
C41 C4 C5 C6 177.3(5) . . . . ?
C41A C4 C5 C6 -171.8(8) . . . . ?
C4 C5 C6 C1 0.7(9) . . . . ?
C2 C1 C6 C5 -1.9(8) . . . . ?
N7 C1 C6 C5 170.9(5) . . . . ?
C2 C1 N7 C8 -72.5(6) . . . . ?
C6 C1 N7 C8 114.8(5) . . . . ?
C2 C1 N7 Ir1 92.7(5) . . . . ?
C6 C1 N7 Ir1 -79.9(5) . . . . ?
C1 N7 C8 C9 165.7(4) . . . . ?
Ir1 N7 C8 C9 2.3(6) . . . . ?
C1 N7 C8 C81 -12.6(6) . . . . ?
Ir1 N7 C8 C81 -176.1(3) . . . . ?
N7 C8 C9 C10 -16.4(8) . . . . ?
C81 C8 C9 C10 162.0(5) . . . . ?
C8 C9 C10 O10 6.8(8) . . . . ?
C8 C9 C10 C11 -169.5(5) . . . . ?
C9 C10 O10 Ir1 15.1(7) . . . . ?
C11 C10 O10 Ir1 -168.5(3) . . . . ?
C25 N12 C13 C14 1.6(7) . . . . ?
Ir1 N12 C13 C14 -179.6(4) . . . . ?
N12 C13 C14 C15 -2.4(8) . . . . ?
C13 C14 C15 C16 0.8(8) . . . . ?
C14 C15 C16 C25 1.3(7) . . . . ?
C14 C15 C16 C17 -177.5(5) . . . . ?
C15 C16 C17 C18 -178.6(5) . . . . ?
C25 C16 C17 C18 2.6(8) . . . . ?
C16 C17 C18 C19 -0.6(8) . . . . ?
C17 C18 C19 C20 179.3(5) . . . . ?
C17 C18 C19 C24 -0.8(7) . . . . ?
C24 C19 C20 C21 -0.1(7) . . . . ?
C18 C19 C20 C21 179.8(5) . . . . ?
C19 C20 C21 C22 -0.9(8) . . . . ?
C20 C21 C22 C23 0.9(7) . . . . ?
C21 C22 C23 C24 0.1(7) . . . . ?
C21 C22 C23 Ir1 -176.0(4) . . . . ?
C20 C19 C24 C25 -179.9(4) . . . . ?
C18 C19 C24 C25 0.2(7) . . . . ?
C20 C19 C24 C23 1.1(7) . . . . ?
C18 C19 C24 C23 -178.9(4) . . . . ?
C22 C23 C24 C19 -1.0(7) . . . . ?
Ir1 C23 C24 C19 175.8(3) . . . . ?
C22 C23 C24 C25 179.9(4) . . . . ?
Ir1 C23 C24 C25 -3.2(5) . . . . ?
C13 N12 C25 C24 -179.3(4) . . . . ?
Ir1 N12 C25 C24 1.8(5) . . . . ?
C13 N12 C25 C16 0.7(6) . . . . ?
Ir1 N12 C25 C16 -178.3(3) . . . . ?
C19 C24 C25 N12 -178.1(4) . . . . ?
C23 C24 C25 N12 1.0(6) . . . . ?
C19 C24 C25 C16 2.0(7) . . . . ?
C23 C24 C25 C16 -179.0(4) . . . . ?
C15 C16 C25 N12 -2.1(7) . . . . ?
C17 C16 C25 N12 176.7(4) . . . . ?
C15 C16 C25 C24 177.8(4) . . . . ?
C17 C16 C25 C24 -3.3(7) . . . . ?
C39 N26 C27 C28 -2.6(7) . . . . ?
Ir1 N26 C27 C28 174.6(4) . . . . ?
N26 C27 C28 C29 1.4(8) . . . . ?
C27 C28 C29 C30 0.6(8) . . . . ?
C28 C29 C30 C39 -1.2(7) . . . . ?
C28 C29 C30 C31 -178.4(5) . . . . ?
C39 C30 C31 C32 -0.8(7) . . . . ?
C29 C30 C31 C32 176.5(5) . . . . ?
C30 C31 C32 C33 0.3(8) . . . . ?
C31 C32 C33 C34 179.6(5) . . . . ?
C31 C32 C33 C38 0.6(8) . . . . ?
C38 C33 C34 C35 0.3(8) . . . . ?
C32 C33 C34 C35 -178.7(5) . . . . ?
C33 C34 C35 C36 -2.3(8) . . . . ?
C34 C35 C36 C37 1.3(8) . . . . ?
C35 C36 C37 C38 1.6(7) . . . . ?
C35 C36 C37 Ir1 -176.6(4) . . . . ?
C34 C33 C38 C39 -179.9(5) . . . . ?
C32 C33 C38 C39 -0.8(7) . . . . ?
C34 C33 C38 C37 2.8(7) . . . . ?
C32 C33 C38 C37 -178.1(5) . . . . ?
C36 C37 C38 C33 -3.8(7) . . . . ?
Ir1 C37 C38 C33 174.8(4) . . . . ?
C36 C37 C38 C39 179.0(4) . . . . ?
Ir1 C37 C38 C39 -2.5(5) . . . . ?
C27 N26 C39 C30 2.0(7) . . . . ?
Ir1 N26 C39 C30 -175.7(4) . . . . ?
C27 N26 C39 C38 179.1(4) . . . . ?
Ir1 N26 C39 C38 1.5(5) . . . . ?
C29 C30 C39 N26 -0.1(7) . . . . ?
C31 C30 C39 N26 177.4(4) . . . . ?
C29 C30 C39 C38 -177.0(4) . . . . ?
C31 C30 C39 C38 0.5(7) . . . . ?
C33 C38 C39 N26 -176.8(4) . . . . ?
C37 C38 C39 N26 0.6(6) . . . . ?
C33 C38 C39 C30 0.3(7) . . . . ?
C37 C38 C39 C30 177.8(4) . . . . ?

_refine_diff_density_max         1.164
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.120



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1814941'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H30 F4 Ir N3 O3'
_chemical_formula_sum            'C40 H30 F4 Ir N3 O3'
_chemical_formula_weight         868.87

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.4734(6)
_cell_length_b                   12.7322(5)
_cell_length_c                   31.2845(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.973(3)
_cell_angle_gamma                90
_cell_volume                     6462.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5737
_cell_measurement_theta_min      3.3160
_cell_measurement_theta_max      28.0190

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             3424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    4.202
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.52062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_reflns_number            14925
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.954
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6750
_reflns_number_gt                5971
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+3.2221P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6750
_refine_ls_number_parameters     463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.40455(2) 0.76341(2) 0.13544(2) 0.01737(6) Uani 1 1 d . . . . .
C1 C 0.5044(2) 0.6377(3) 0.08061(10) 0.0209(7) Uani 1 1 d . . . . .
C2 C 0.5346(2) 0.6958(3) 0.04963(10) 0.0221(7) Uani 1 1 d . . . . .
F2 F 0.48155(15) 0.75130(15) 0.02038(7) 0.0306(5) Uani 1 1 d . . . . .
C3 C 0.6165(2) 0.7012(3) 0.04779(12) 0.0268(8) Uani 1 1 d . . . . .
F3 F 0.64204(17) 0.76006(16) 0.01650(8) 0.0390(6) Uani 1 1 d . . . . .
C4 C 0.6747(2) 0.6485(3) 0.07756(12) 0.0280(8) Uani 1 1 d . . . . .
O41 O 0.75771(14) 0.6517(2) 0.07748(9) 0.0371(7) Uani 1 1 d . . . . .
C42 C 0.7961(3) 0.7533(3) 0.08178(18) 0.0415(12) Uani 1 1 d . . . . .
H42A H 0.7643 0.8004 0.0979 0.050 Uiso 1 1 calc R U . . .
H42B H 0.7950 0.7838 0.0526 0.050 Uiso 1 1 calc R U . . .
C43 C 0.8826(3) 0.7474(3) 0.10488(18) 0.0466(13) Uani 1 1 d . . . . .
H43A H 0.9109 0.6874 0.0937 0.056 Uiso 1 1 calc R U . . .
H43B H 0.9123 0.8125 0.0998 0.056 Uiso 1 1 calc R U . . .
O44 O 0.8833(2) 0.7349(2) 0.14844(13) 0.0521(9) Uani 1 1 d . . . . .
C45 C 0.9654(3) 0.7327(4) 0.1716(2) 0.0650(18) Uani 1 1 d . . . . .
H45A H 0.9962 0.6767 0.1600 0.098 Uiso 1 1 calc R U . . .
H45B H 0.9647 0.7194 0.2024 0.098 Uiso 1 1 calc R U . . .
H45C H 0.9920 0.8004 0.1684 0.098 Uiso 1 1 calc R U . . .
C5 C 0.6455(2) 0.5876(3) 0.10780(11) 0.0244(8) Uani 1 1 d . . . . .
F5 F 0.69850(12) 0.53392(17) 0.13752(7) 0.0327(5) Uani 1 1 d . . . . .
C6 C 0.5626(2) 0.5812(3) 0.10885(11) 0.0213(7) Uani 1 1 d . . . . .
F6 F 0.53779(11) 0.51992(16) 0.13917(6) 0.0275(4) Uani 1 1 d . . . . .
N7 N 0.42179(16) 0.6474(2) 0.08775(9) 0.0191(6) Uani 1 1 d . . . . .
C8 C 0.3627(2) 0.5940(3) 0.06265(11) 0.0230(7) Uani 1 1 d . . . . .
C81 C 0.3857(2) 0.5125(3) 0.03189(12) 0.0296(8) Uani 1 1 d . . . . .
H81A H 0.4018 0.5475 0.0067 0.044 Uiso 1 1 calc R U . . .
H81B H 0.3383 0.4667 0.0222 0.044 Uiso 1 1 calc R U . . .
H81C H 0.4319 0.4704 0.0468 0.044 Uiso 1 1 calc R U . . .
C9 C 0.2783(2) 0.6082(3) 0.06394(11) 0.0264(8) Uani 1 1 d . . . . .
H9 H 0.2421 0.5577 0.0485 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2412(2) 0.6857(3) 0.08470(11) 0.0262(8) Uani 1 1 d . . . . .
O10 O 0.27591(16) 0.75779(17) 0.10987(9) 0.0258(6) Uani 1 1 d . . . . .
C11 C 0.1480(2) 0.6892(3) 0.07717(12) 0.0321(8) Uani 1 1 d . . . . .
H11A H 0.1296 0.7170 0.1031 0.048 Uiso 1 1 calc R U . . .
H11B H 0.1260 0.6182 0.0712 0.048 Uiso 1 1 calc R U . . .
H11C H 0.1280 0.7348 0.0523 0.048 Uiso 1 1 calc R U . . .
N12 N 0.38265(16) 0.6567(2) 0.18111(9) 0.0203(6) Uani 1 1 d . . . . .
C13 C 0.3768(2) 0.5519(3) 0.17721(12) 0.0261(8) Uani 1 1 d . . . . .
H13 H 0.3844 0.5200 0.1507 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3598(2) 0.4886(3) 0.21094(12) 0.0328(9) Uani 1 1 d . . . . .
H14 H 0.3558 0.4147 0.2072 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3489(2) 0.5324(3) 0.24946(13) 0.0356(9) Uani 1 1 d . . . . .
H15 H 0.3389 0.4890 0.2727 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3526(2) 0.6424(3) 0.25442(12) 0.0297(8) Uani 1 1 d . . . . .
C17 C 0.3363(2) 0.6990(3) 0.29180(12) 0.0342(9) Uani 1 1 d . . . . .
H17 H 0.3233 0.6611 0.3159 0.041 Uiso 1 1 calc R U . . .
C18 C 0.3391(2) 0.8046(3) 0.29334(12) 0.0329(9) Uani 1 1 d . . . . .
H18 H 0.3278 0.8393 0.3185 0.039 Uiso 1 1 calc R U . . .
C19 C 0.3587(2) 0.8665(3) 0.25810(11) 0.0256(8) Uani 1 1 d . . . . .
C20 C 0.3635(2) 0.9760(3) 0.25821(12) 0.0294(8) Uani 1 1 d . . . . .
H20 H 0.3545 1.0145 0.2830 0.035 Uiso 1 1 calc R U . . .
C21 C 0.3814(2) 1.0280(3) 0.22243(12) 0.0273(8) Uani 1 1 d . . . . .
H21 H 0.3861 1.1024 0.2232 0.033 Uiso 1 1 calc R U . . .
C22 C 0.3929(2) 0.9740(3) 0.18453(11) 0.0236(7) Uani 1 1 d . . . . .
H22 H 0.4042 1.0124 0.1602 0.028 Uiso 1 1 calc R U . . .
C23 C 0.38792(19) 0.8648(3) 0.18249(11) 0.0199(7) Uani 1 1 d . . . . .
C24 C 0.37258(19) 0.8134(3) 0.22042(11) 0.0221(7) Uani 1 1 d . . . . .
C25 C 0.3697(2) 0.7022(3) 0.21915(11) 0.0241(7) Uani 1 1 d . . . . .
N26 N 0.42910(18) 0.8802(2) 0.09504(9) 0.0223(6) Uani 1 1 d . . . . .
C27 C 0.3755(2) 0.9267(3) 0.06352(11) 0.0293(8) Uani 1 1 d . . . . .
H27 H 0.3199 0.9035 0.0579 0.035 Uiso 1 1 calc R U . . .
C28 C 0.3997(3) 1.0083(3) 0.03877(12) 0.0369(10) Uani 1 1 d . . . . .
H28 H 0.3605 1.0405 0.0168 0.044 Uiso 1 1 calc R U . . .
C29 C 0.4805(3) 1.0424(3) 0.04604(13) 0.0387(10) Uani 1 1 d . . . . .
H29 H 0.4971 1.0982 0.0293 0.046 Uiso 1 1 calc R U . . .
C30 C 0.5378(2) 0.9938(3) 0.07834(12) 0.0311(9) Uani 1 1 d . . . . .
C31 C 0.6239(3) 1.0197(3) 0.08926(14) 0.0397(10) Uani 1 1 d . . . . .
H31 H 0.6453 1.0744 0.0739 0.048 Uiso 1 1 calc R U . . .
C32 C 0.6746(3) 0.9688(3) 0.12052(14) 0.0360(10) Uani 1 1 d . . . . .
H32 H 0.7312 0.9881 0.1266 0.043 Uiso 1 1 calc R U . . .
C33 C 0.6457(2) 0.8856(3) 0.14519(12) 0.0283(8) Uani 1 1 d . . . . .
C34 C 0.6960(2) 0.8268(3) 0.17796(12) 0.0305(8) Uani 1 1 d . . . . .
H34 H 0.7537 0.8391 0.1842 0.037 Uiso 1 1 calc R U . . .
C35 C 0.6611(2) 0.7519(3) 0.20077(14) 0.0299(9) Uani 1 1 d . . . . .
H35 H 0.6949 0.7144 0.2234 0.036 Uiso 1 1 calc R U . . .
C36 C 0.5765(2) 0.7298(3) 0.19123(12) 0.0250(8) Uani 1 1 d . . . . .
H36 H 0.5548 0.6778 0.2079 0.030 Uiso 1 1 calc R U . . .
C37 C 0.5229(2) 0.7805(3) 0.15859(11) 0.0189(7) Uani 1 1 d . . . . .
C38 C 0.5614(2) 0.8594(3) 0.13601(11) 0.0220(7) Uani 1 1 d . . . . .
C39 C 0.5092(2) 0.9130(3) 0.10245(11) 0.0244(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C37 1.970(3) . ?
Ir1 C23 2.012(3) . ?
Ir1 N26 2.037(3) . ?
Ir1 N12 2.049(3) . ?
Ir1 O10 2.133(3) . ?
Ir1 N7 2.153(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.387(5) . ?
C1 N7 1.422(4) . ?
C2 F2 1.350(4) . ?
C2 C3 1.362(5) . ?
C3 F3 1.356(4) . ?
C3 C4 1.388(5) . ?
C4 O41 1.369(4) . ?
C4 C5 1.373(5) . ?
O41 C42 1.436(4) . ?
C42 C43 1.485(7) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 O44 1.370(7) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
O44 C45 1.420(6) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C5 F5 1.346(4) . ?
C5 C6 1.374(4) . ?
C6 F6 1.346(4) . ?
N7 C8 1.327(4) . ?
C8 C9 1.410(5) . ?
C8 C81 1.507(5) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C9 C10 1.381(5) . ?
C9 H9 0.9500 . ?
C10 O10 1.278(4) . ?
C10 C11 1.513(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N12 C13 1.342(4) . ?
N12 C25 1.374(4) . ?
C13 C14 1.394(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.368(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.409(5) . ?
C15 H15 0.9500 . ?
C16 C25 1.409(5) . ?
C16 C17 1.438(5) . ?
C17 C18 1.345(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.437(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(5) . ?
C19 C24 1.412(5) . ?
C20 C21 1.376(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.412(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.393(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.416(4) . ?
C24 C25 1.416(5) . ?
N26 C27 1.342(4) . ?
N26 C39 1.365(4) . ?
C27 C28 1.394(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.402(5) . ?
C29 H29 0.9500 . ?
C30 C39 1.404(4) . ?
C30 C31 1.438(5) . ?
C31 C32 1.339(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.439(5) . ?
C32 H32 0.9500 . ?
C33 C38 1.409(4) . ?
C33 C34 1.415(5) . ?
C34 C35 1.376(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.402(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.388(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.438(4) . ?
C38 C39 1.412(5) . ?

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
C37 Ir1 C23 84.93(13) . . ?
C37 Ir1 N26 81.81(13) . . ?
C23 Ir1 N26 93.00(13) . . ?
C37 Ir1 N12 95.70(12) . . ?
C23 Ir1 N12 81.54(13) . . ?
N26 Ir1 N12 174.20(11) . . ?
C37 Ir1 O10 175.58(11) . . ?
C23 Ir1 O10 92.50(11) . . ?
N26 Ir1 O10 94.76(11) . . ?
N12 Ir1 O10 87.46(10) . . ?
C37 Ir1 N7 95.14(12) . . ?
C23 Ir1 N7 176.58(11) . . ?
N26 Ir1 N7 90.39(11) . . ?
N12 Ir1 N7 95.06(11) . . ?
O10 Ir1 N7 87.64(10) . . ?
C2 C1 C6 115.6(3) . . ?
C2 C1 N7 122.4(3) . . ?
C6 C1 N7 121.4(3) . . ?
F2 C2 C3 118.3(3) . . ?
F2 C2 C1 119.2(3) . . ?
C3 C2 C1 122.5(3) . . ?
F3 C3 C2 119.5(3) . . ?
F3 C3 C4 119.1(3) . . ?
C2 C3 C4 121.4(3) . . ?
O41 C4 C5 119.2(3) . . ?
O41 C4 C3 124.0(3) . . ?
C5 C4 C3 116.9(3) . . ?
C4 O41 C42 116.7(3) . . ?
O41 C42 C43 111.7(3) . . ?
O41 C42 H42A 109.3 . . ?
C43 C42 H42A 109.3 . . ?
O41 C42 H42B 109.3 . . ?
C43 C42 H42B 109.3 . . ?
H42A C42 H42B 107.9 . . ?
O44 C43 C42 109.3(4) . . ?
O44 C43 H43A 109.8 . . ?
C42 C43 H43A 109.8 . . ?
O44 C43 H43B 109.8 . . ?
C42 C43 H43B 109.8 . . ?
H43A C43 H43B 108.3 . . ?
C43 O44 C45 110.6(5) . . ?
O44 C45 H45A 109.5 . . ?
O44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
O44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
F5 C5 C4 120.0(3) . . ?
F5 C5 C6 118.8(3) . . ?
C4 C5 C6 121.2(3) . . ?
F6 C6 C5 118.4(3) . . ?
F6 C6 C1 119.2(3) . . ?
C5 C6 C1 122.3(3) . . ?
C8 N7 C1 119.1(3) . . ?
C8 N7 Ir1 126.2(2) . . ?
C1 N7 Ir1 114.4(2) . . ?
N7 C8 C9 122.9(3) . . ?
N7 C8 C81 119.4(3) . . ?
C9 C8 C81 117.7(3) . . ?
C8 C81 H81A 109.5 . . ?
C8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C10 C9 C8 128.6(3) . . ?
C10 C9 H9 115.7 . . ?
C8 C9 H9 115.7 . . ?
O10 C10 C9 128.0(3) . . ?
O10 C10 C11 114.1(3) . . ?
C9 C10 C11 117.9(3) . . ?
C10 O10 Ir1 124.4(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 N12 C25 118.6(3) . . ?
C13 N12 Ir1 127.9(2) . . ?
C25 N12 Ir1 113.4(2) . . ?
N12 C13 C14 121.8(3) . . ?
N12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C25 C16 C15 117.5(3) . . ?
C25 C16 C17 117.2(4) . . ?
C15 C16 C17 125.2(3) . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 122.1(3) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C20 C19 C24 117.6(3) . . ?
C20 C19 C18 124.5(3) . . ?
C24 C19 C18 117.9(4) . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 121.8(3) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 116.2(3) . . ?
C22 C23 Ir1 131.2(3) . . ?
C24 C23 Ir1 112.5(2) . . ?
C19 C24 C25 119.5(3) . . ?
C19 C24 C23 123.8(3) . . ?
C25 C24 C23 116.7(3) . . ?
N12 C25 C16 122.2(3) . . ?
N12 C25 C24 115.9(3) . . ?
C16 C25 C24 121.9(3) . . ?
C27 N26 C39 118.9(3) . . ?
C27 N26 Ir1 127.0(3) . . ?
C39 N26 Ir1 114.1(2) . . ?
N26 C27 C28 121.5(4) . . ?
N26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C29 C28 C27 120.1(4) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 119.3(3) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C29 C30 C39 117.6(3) . . ?
C29 C30 C31 125.7(3) . . ?
C39 C30 C31 116.7(4) . . ?
C32 C31 C30 121.9(3) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C31 C32 C33 121.7(4) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C38 C33 C34 117.0(3) . . ?
C38 C33 C32 118.1(4) . . ?
C34 C33 C32 124.9(3) . . ?
C35 C34 C33 119.9(3) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 121.2(4) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C37 C36 C35 123.1(4) . . ?
C37 C36 H36 118.5 . . ?
C35 C36 H36 118.5 . . ?
C36 C37 C38 114.0(3) . . ?
C36 C37 Ir1 133.0(3) . . ?
C38 C37 Ir1 112.9(2) . . ?
C33 C38 C39 119.3(3) . . ?
C33 C38 C37 124.7(3) . . ?
C39 C38 C37 116.0(3) . . ?
N26 C39 C30 122.5(3) . . ?
N26 C39 C38 115.1(3) . . ?
C30 C39 C38 122.4(3) . . ?

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
C6 C1 C2 F2 178.7(3) . . . . ?
N7 C1 C2 F2 -10.9(5) . . . . ?
C6 C1 C2 C3 -2.6(5) . . . . ?
N7 C1 C2 C3 167.9(3) . . . . ?
F2 C2 C3 F3 -1.1(5) . . . . ?
C1 C2 C3 F3 -179.9(3) . . . . ?
F2 C2 C3 C4 178.2(3) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
F3 C3 C4 O41 -0.1(5) . . . . ?
C2 C3 C4 O41 -179.5(3) . . . . ?
F3 C3 C4 C5 -178.2(3) . . . . ?
C2 C3 C4 C5 2.5(5) . . . . ?
C5 C4 O41 C42 -123.1(4) . . . . ?
C3 C4 O41 C42 58.9(5) . . . . ?
C4 O41 C42 C43 148.4(4) . . . . ?
O41 C42 C43 O44 -76.4(5) . . . . ?
C42 C43 O44 C45 -177.9(3) . . . . ?
O41 C4 C5 F5 1.5(5) . . . . ?
C3 C4 C5 F5 179.7(3) . . . . ?
O41 C4 C5 C6 -179.4(3) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
F5 C5 C6 F6 -1.1(5) . . . . ?
C4 C5 C6 F6 179.8(3) . . . . ?
F5 C5 C6 C1 177.1(3) . . . . ?
C4 C5 C6 C1 -2.0(5) . . . . ?
C2 C1 C6 F6 -178.0(3) . . . . ?
N7 C1 C6 F6 11.5(5) . . . . ?
C2 C1 C6 C5 3.8(5) . . . . ?
N7 C1 C6 C5 -166.7(3) . . . . ?
C2 C1 N7 C8 83.4(4) . . . . ?
C6 C1 N7 C8 -106.7(4) . . . . ?
C2 C1 N7 Ir1 -90.3(3) . . . . ?
C6 C1 N7 Ir1 79.6(3) . . . . ?
C1 N7 C8 C9 -172.3(3) . . . . ?
Ir1 N7 C8 C9 0.7(5) . . . . ?
C1 N7 C8 C81 9.1(4) . . . . ?
Ir1 N7 C8 C81 -177.9(2) . . . . ?
N7 C8 C9 C10 10.7(6) . . . . ?
C81 C8 C9 C10 -170.7(3) . . . . ?
C8 C9 C10 O10 -5.3(6) . . . . ?
C8 C9 C10 C11 173.9(3) . . . . ?
C9 C10 O10 Ir1 -10.5(5) . . . . ?
C11 C10 O10 Ir1 170.2(2) . . . . ?
C25 N12 C13 C14 -1.5(5) . . . . ?
Ir1 N12 C13 C14 -178.6(3) . . . . ?
N12 C13 C14 C15 -0.3(6) . . . . ?
C13 C14 C15 C16 1.8(6) . . . . ?
C14 C15 C16 C25 -1.6(6) . . . . ?
C14 C15 C16 C17 175.2(4) . . . . ?
C25 C16 C17 C18 -1.5(5) . . . . ?
C15 C16 C17 C18 -178.2(4) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 -179.1(3) . . . . ?
C17 C18 C19 C24 2.0(5) . . . . ?
C24 C19 C20 C21 0.0(5) . . . . ?
C18 C19 C20 C21 -178.9(3) . . . . ?
C19 C20 C21 C22 1.8(5) . . . . ?
C20 C21 C22 C23 -1.2(5) . . . . ?
C21 C22 C23 C24 -1.2(5) . . . . ?
C21 C22 C23 Ir1 -177.6(2) . . . . ?
C20 C19 C24 C25 178.9(3) . . . . ?
C18 C19 C24 C25 -2.2(5) . . . . ?
C20 C19 C24 C23 -2.5(5) . . . . ?
C18 C19 C24 C23 176.4(3) . . . . ?
C22 C23 C24 C19 3.1(5) . . . . ?
Ir1 C23 C24 C19 -179.9(3) . . . . ?
C22 C23 C24 C25 -178.3(3) . . . . ?
Ir1 C23 C24 C25 -1.2(4) . . . . ?
C13 N12 C25 C16 1.7(5) . . . . ?
Ir1 N12 C25 C16 179.2(3) . . . . ?
C13 N12 C25 C24 -176.9(3) . . . . ?
Ir1 N12 C25 C24 0.7(4) . . . . ?
C15 C16 C25 N12 -0.1(5) . . . . ?
C17 C16 C25 N12 -177.2(3) . . . . ?
C15 C16 C25 C24 178.3(3) . . . . ?
C17 C16 C25 C24 1.3(5) . . . . ?
C19 C24 C25 N12 179.1(3) . . . . ?
C23 C24 C25 N12 0.4(4) . . . . ?
C19 C24 C25 C16 0.5(5) . . . . ?
C23 C24 C25 C16 -178.2(3) . . . . ?
C39 N26 C27 C28 -0.9(5) . . . . ?
Ir1 N26 C27 C28 178.1(2) . . . . ?
N26 C27 C28 C29 0.7(5) . . . . ?
C27 C28 C29 C30 0.3(5) . . . . ?
C28 C29 C30 C39 -1.1(5) . . . . ?
C28 C29 C30 C31 179.2(3) . . . . ?
C29 C30 C31 C32 -179.6(4) . . . . ?
C39 C30 C31 C32 0.7(5) . . . . ?
C30 C31 C32 C33 -0.4(6) . . . . ?
C31 C32 C33 C38 -0.9(5) . . . . ?
C31 C32 C33 C34 178.5(4) . . . . ?
C38 C33 C34 C35 -3.4(5) . . . . ?
C32 C33 C34 C35 177.3(3) . . . . ?
C33 C34 C35 C36 2.1(5) . . . . ?
C34 C35 C36 C37 0.4(6) . . . . ?
C35 C36 C37 C38 -1.3(5) . . . . ?
C35 C36 C37 Ir1 176.4(3) . . . . ?
C34 C33 C38 C39 -177.6(3) . . . . ?
C32 C33 C38 C39 1.8(5) . . . . ?
C34 C33 C38 C37 2.4(5) . . . . ?
C32 C33 C38 C37 -178.1(3) . . . . ?
C36 C37 C38 C33 -0.1(5) . . . . ?
Ir1 C37 C38 C33 -178.3(3) . . . . ?
C36 C37 C38 C39 179.9(3) . . . . ?
Ir1 C37 C38 C39 1.7(4) . . . . ?
C27 N26 C39 C30 0.1(5) . . . . ?
Ir1 N26 C39 C30 -179.1(2) . . . . ?
C27 N26 C39 C38 -179.6(3) . . . . ?
Ir1 N26 C39 C38 1.2(4) . . . . ?
C29 C30 C39 N26 0.9(5) . . . . ?
C31 C30 C39 N26 -179.4(3) . . . . ?
C29 C30 C39 C38 -179.4(3) . . . . ?
C31 C30 C39 C38 0.3(5) . . . . ?
C33 C38 C39 N26 178.1(3) . . . . ?
C37 C38 C39 N26 -1.9(4) . . . . ?
C33 C38 C39 C30 -1.6(5) . . . . ?
C37 C38 C39 C30 178.4(3) . . . . ?

_refine_diff_density_max         2.093
_refine_diff_density_min         -1.061
_refine_diff_density_rms         0.103

_shelxl_version_number           2013-4



