# 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_170405zyx_CF3ppyIrPyPzMe_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1819964'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H22 F6 Ir N5'
_chemical_formula_weight         794.75

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'

_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                   17.666(2)
_cell_length_b                   16.9546(19)
_cell_length_c                   21.093(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.461(2)
_cell_angle_gamma                90
_cell_volume                     6117.7(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6472
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             3088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    4.433
_shelx_estimated_absorpt_T_min   0.381
_shelx_estimated_absorpt_T_max   0.442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4847
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33806
_diffrn_reflns_av_unetI/netI     0.1226
_diffrn_reflns_av_R_equivalents  0.1090
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.190
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10774
_reflns_number_gt                6427
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0746P)²+18.0050P] 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         10774
_refine_ls_number_parameters     813
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1745
_refine_ls_wR_factor_gt          0.1465
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.3146(7) 0.3923(8) 0.7834(6) 0.042(3) Uani 1 1 d . . . . .
C2 C 0.3731(8) 0.4036(8) 0.8413(7) 0.051(4) Uani 1 1 d . . . . .
H2 H 0.372726 0.448010 0.867050 0.062 Uiso 1 1 calc R U . . .
C3 C 0.4313(9) 0.3478(10) 0.8593(8) 0.061(4) Uani 1 1 d . . . . .
C4 C 0.4931(11) 0.3581(11) 0.9189(9) 0.073(5) Uani 1 1 d . . . . .
C5 C 0.4330(10) 0.2803(9) 0.8250(9) 0.071(5) Uani 1 1 d . . . . .
H5 H 0.472138 0.243129 0.839590 0.085 Uiso 1 1 calc R U . . .
C6 C 0.3766(9) 0.2681(9) 0.7691(8) 0.064(4) Uani 1 1 d . . . . .
H6 H 0.377351 0.222610 0.744633 0.077 Uiso 1 1 calc R U . . .
C7 C 0.3168(7) 0.3244(7) 0.7481(7) 0.043(3) Uani 1 1 d . . . . .
C8 C 0.2578(8) 0.3178(8) 0.6865(7) 0.047(4) Uani 1 1 d . . . . .
C9 C 0.2517(9) 0.2572(9) 0.6411(7) 0.064(4) Uani 1 1 d . . . . .
H9 H 0.286763 0.215291 0.649184 0.077 Uiso 1 1 calc R U . . .
C10 C 0.1939(11) 0.2598(11) 0.5846(8) 0.082(5) Uani 1 1 d . . . . .
H10 H 0.189676 0.220454 0.553155 0.099 Uiso 1 1 calc R U . . .
C11 C 0.1422(10) 0.3215(10) 0.5749(9) 0.077(5) Uani 1 1 d . . . . .
H11 H 0.101592 0.323512 0.537136 0.092 Uiso 1 1 calc R U . . .
C12 C 0.1498(9) 0.3794(9) 0.6200(7) 0.060(4) Uani 1 1 d . . . . .
H12 H 0.114566 0.421247 0.612002 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2902(9) 0.5363(8) 0.7039(8) 0.060(4) Uani 1 1 d . . . . .
C14 C 0.3093(8) 0.5267(8) 0.6447(7) 0.051(4) Uani 1 1 d . . . . .
H14 H 0.293569 0.481494 0.619925 0.062 Uiso 1 1 calc R U . . .
C15 C 0.3529(8) 0.5856(11) 0.6219(8) 0.072(5) Uani 1 1 d . U . . .
C16 C 0.3689(13) 0.5742(15) 0.5552(12) 0.099(7) Uani 1 1 d . . . . .
C17 C 0.3755(11) 0.6530(12) 0.6578(10) 0.100(7) Uani 1 1 d . U . . .
H17 H 0.402891 0.692134 0.642054 0.120 Uiso 1 1 calc R U . . .
C18 C 0.3573(11) 0.6624(11) 0.7178(11) 0.097(6) Uani 1 1 d . . . . .
H18 H 0.372959 0.707939 0.741997 0.117 Uiso 1 1 calc R U . . .
C19 C 0.3166(9) 0.6057(9) 0.7418(8) 0.062(4) Uani 1 1 d . . . . .
C20 C 0.2961(10) 0.6106(9) 0.8023(9) 0.068(5) Uani 1 1 d . . . . .
C21 C 0.3155(12) 0.6726(11) 0.8443(11) 0.106(7) Uani 1 1 d . . . . .
H21 H 0.341925 0.715756 0.832978 0.127 Uiso 1 1 calc R U . . .
C22 C 0.2960(14) 0.6715(13) 0.9031(12) 0.124(9) Uani 1 1 d . . . . .
H22 H 0.313427 0.711159 0.933722 0.149 Uiso 1 1 calc R U . . .
C23 C 0.2510(14) 0.6120(13) 0.9165(10) 0.114(8) Uani 1 1 d . . . . .
H23 H 0.235840 0.611099 0.955697 0.137 Uiso 1 1 calc R U . . .
C24 C 0.2275(10) 0.5514(10) 0.8697(8) 0.081(5) Uani 1 1 d . . . . .
H24 H 0.193969 0.512039 0.876912 0.097 Uiso 1 1 calc R U . A 2
C25 C 0.1049(9) 0.5777(8) 0.6530(7) 0.059(4) Uani 1 1 d . . . . .
H25 H 0.147760 0.590068 0.636761 0.071 Uiso 1 1 calc R U . . .
C26 C 0.0358(9) 0.6153(9) 0.6256(8) 0.062(4) Uani 1 1 d . . . . .
H26 H 0.031916 0.653356 0.593133 0.074 Uiso 1 1 calc R U . . .
C27 C -0.0274(10) 0.5937(10) 0.6486(8) 0.077(5) Uani 1 1 d . . . . .
H27 H -0.076306 0.615510 0.630315 0.093 Uiso 1 1 calc R U . . .
C28 C -0.0186(9) 0.5394(10) 0.6992(8) 0.068(4) Uani 1 1 d . . . . .
H28 H -0.060496 0.527617 0.716871 0.082 Uiso 1 1 calc R U . . .
C29 C 0.0527(8) 0.5029(8) 0.7230(7) 0.048(3) Uani 1 1 d . . . . .
C30 C 0.0682(8) 0.4433(8) 0.7733(7) 0.050(4) Uani 1 1 d . . . . .
C31 C 0.0260(9) 0.4118(9) 0.8132(7) 0.065(4) Uani 1 1 d . . . . .
H31 H -0.026222 0.421173 0.811876 0.077 Uiso 1 1 calc R U . . .
C32 C 0.0771(10) 0.3632(8) 0.8559(8) 0.057(4) Uani 1 1 d . . . . .
C33 C 0.0660(10) 0.3142(10) 0.9113(8) 0.089(6) Uani 1 1 d . . . . .
H33A H 0.057985 0.260226 0.897602 0.133 Uiso 1 1 calc R U . . .
H33B H 0.021263 0.332824 0.925014 0.133 Uiso 1 1 calc R U . . .
H33C H 0.111624 0.317987 0.947236 0.133 Uiso 1 1 calc R U . . .
C34 C 0.2128(7) 0.5675(7) 0.3192(7) 0.047(3) Uani 1 1 d . . . . .
C35 C 0.1943(8) 0.5522(8) 0.3798(7) 0.055(4) Uani 1 1 d . . . . .
H35 H 0.216096 0.508286 0.404099 0.066 Uiso 1 1 calc R U . . .
C36 C 0.1444(9) 0.6011(10) 0.4039(8) 0.065(4) Uani 1 1 d . . . . .
C37 C 0.1222(12) 0.5782(12) 0.4663(9) 0.078(5) Uani 1 1 d . U . . .
C38 C 0.1129(10) 0.6677(11) 0.3694(9) 0.089(6) Uani 1 1 d . . . . .
H38 H 0.080001 0.700374 0.385899 0.106 Uiso 1 1 calc R U . . .
C39 C 0.1297(10) 0.6856(10) 0.3117(8) 0.078(5) Uani 1 1 d . . . . .
H39 H 0.108595 0.730838 0.289071 0.094 Uiso 1 1 calc R U . . .
C40 C 0.1776(8) 0.6374(9) 0.2862(8) 0.060(4) Uani 1 1 d . . . . .
C41 C 0.1971(9) 0.6523(8) 0.2241(7) 0.059(4) Uani 1 1 d . . . . .
C42 C 0.1711(10) 0.7149(9) 0.1832(9) 0.078(5) Uani 1 1 d . . . . .
H42 H 0.139665 0.753311 0.194976 0.093 Uiso 1 1 calc R U . . .
C43 C 0.1917(14) 0.7206(11) 0.1247(10) 0.113(7) Uani 1 1 d . U . . .
H43 H 0.169996 0.759680 0.094700 0.136 Uiso 1 1 calc R U . . .
C44 C 0.2435(12) 0.6690(10) 0.1111(8) 0.087(6) Uani 1 1 d . U . . .
H44 H 0.261830 0.675661 0.073819 0.105 Uiso 1 1 calc R U . . .
C45 C 0.2693(10) 0.6064(8) 0.1526(7) 0.067(5) Uani 1 1 d . . . . .
H45 H 0.302213 0.569194 0.141080 0.081 Uiso 1 1 calc R U . B 2
C46 C 0.1935(9) 0.4344(8) 0.2319(7) 0.050(4) Uani 1 1 d . . . . .
C47 C 0.1366(8) 0.4426(7) 0.1773(7) 0.048(4) Uani 1 1 d . . . . .
H47 H 0.134866 0.488323 0.152588 0.058 Uiso 1 1 calc R U . C 2
C48 C 0.0788(9) 0.3844(9) 0.1556(8) 0.063(4) Uani 1 1 d . . . . .
C49 C 0.0156(12) 0.3964(14) 0.0948(9) 0.087(6) Uani 1 1 d . . . . .
C50 C 0.0793(9) 0.3179(9) 0.1923(8) 0.064(4) Uani 1 1 d . . . . .
H50 H 0.040722 0.279939 0.178726 0.077 Uiso 1 1 calc R U . . .
C51 C 0.1368(9) 0.3067(9) 0.2495(7) 0.059(4) Uani 1 1 d . . . . .
H51 H 0.138821 0.260515 0.273620 0.071 Uiso 1 1 calc R U . . .
C52 C 0.1929(8) 0.3680(8) 0.2706(7) 0.046(3) Uani 1 1 d . . . . .
C53 C 0.2551(8) 0.3591(8) 0.3313(7) 0.049(4) Uani 1 1 d . . . . .
C54 C 0.2640(9) 0.2971(9) 0.3740(8) 0.060(4) Uani 1 1 d . . . . .
H54 H 0.230023 0.254324 0.365425 0.072 Uiso 1 1 calc R U . . .
C55 C 0.3232(11) 0.2992(10) 0.4288(8) 0.077(5) Uani 1 1 d . . . . .
H55 H 0.327796 0.259010 0.459538 0.092 Uiso 1 1 calc R U . . .
C56 C 0.3765(9) 0.3595(9) 0.4397(8) 0.070(5) Uani 1 1 d . . . . .
H56 H 0.419363 0.360121 0.475832 0.084 Uiso 1 1 calc R U . . .
C57 C 0.3626(9) 0.4202(8) 0.3934(7) 0.056(4) Uani 1 1 d . . . . .
H57 H 0.396343 0.463135 0.401184 0.067 Uiso 1 1 calc R U . . .
C58 C 0.3965(9) 0.6284(8) 0.3672(8) 0.060(4) Uani 1 1 d . . . . .
H58 H 0.354144 0.640437 0.384174 0.072 Uiso 1 1 calc R U . . .
C59 C 0.4658(10) 0.6647(9) 0.3908(9) 0.077(5) Uani 1 1 d . . . . .
H59 H 0.471887 0.700258 0.425259 0.092 Uiso 1 1 calc R U . . .
C60 C 0.5272(11) 0.6489(13) 0.3637(11) 0.099(6) Uani 1 1 d . . . . .
H60 H 0.574485 0.675060 0.379107 0.119 Uiso 1 1 calc R U . . .
C61 C 0.5195(10) 0.5963(10) 0.3152(10) 0.079(5) Uani 1 1 d . . . . .
H61 H 0.561162 0.585609 0.296928 0.094 Uiso 1 1 calc R U . . .
C62 C 0.4497(8) 0.5586(8) 0.2929(8) 0.060(4) Uani 1 1 d . . . . .
C63 C 0.4341(9) 0.5013(8) 0.2425(8) 0.061(4) Uani 1 1 d . . . . .
C64 C 0.4794(10) 0.4692(10) 0.2012(10) 0.079(5) Uani 1 1 d . . . . .
H64 H 0.531450 0.479228 0.202333 0.095 Uiso 1 1 calc R U . . .
C65 C 0.4281(12) 0.4199(10) 0.1591(10) 0.090(6) Uani 1 1 d . . . . .
C66 C 0.4408(13) 0.3733(12) 0.1033(10) 0.122(8) Uani 1 1 d . . . . .
H66A H 0.464766 0.323844 0.118949 0.182 Uiso 1 1 calc R U . . .
H66B H 0.474440 0.402050 0.082106 0.182 Uiso 1 1 calc R U . . .
H66C H 0.391547 0.363840 0.072584 0.182 Uiso 1 1 calc R U . . .
F1 F 0.5659(7) 0.3553(9) 0.9097(6) 0.148(5) Uani 1 1 d . . . . .
F2 F 0.4970(8) 0.3061(8) 0.9656(6) 0.151(5) Uani 1 1 d . . . . .
F3 F 0.4945(7) 0.4257(8) 0.9495(6) 0.129(4) Uani 1 1 d . . . . .
F4 F 0.3381(11) 0.5144(10) 0.5224(7) 0.164(7) Uani 1 1 d . . . . .
F5 F 0.4448(8) 0.5676(16) 0.5624(7) 0.247(12) Uani 1 1 d . . . . .
F6 F 0.3536(13) 0.6346(10) 0.5196(8) 0.212(9) Uani 1 1 d . . . . .
F7 F 0.1513(11) 0.6315(9) 0.5107(6) 0.183(8) Uani 1 1 d . . . . .
F8 F 0.0457(7) 0.5806(10) 0.4592(6) 0.163(6) Uani 1 1 d . . . . .
F9 F 0.1454(9) 0.5101(8) 0.4884(6) 0.142(6) Uani 1 1 d . U . . .
F10 F 0.0235(9) 0.4524(10) 0.0599(7) 0.203(9) Uani 1 1 d . . . . .
F11 F -0.0525(8) 0.4051(11) 0.1058(7) 0.168(7) Uani 1 1 d . . . . .
F12 F 0.0047(9) 0.3326(9) 0.0579(6) 0.153(6) Uani 1 1 d . . . . .
Ir1 Ir 0.22285(3) 0.46473(3) 0.74469(3) 0.04182(18) Uani 0.98 1 d . U P D 1
Ir2 Ir 0.28249(3) 0.50938(3) 0.27459(3) 0.04130(17) Uani 0.98 1 d . U P E 1
N1 N 0.2050(6) 0.3788(6) 0.6746(5) 0.041(3) Uani 1 1 d . . . . .
N2 N 0.2527(7) 0.5500(7) 0.8156(6) 0.060(3) Uani 1 1 d . . . . .
N3 N 0.1156(6) 0.5247(6) 0.7012(6) 0.051(3) Uani 1 1 d . . . . .
N4 N 0.1409(6) 0.4140(5) 0.7897(5) 0.039(3) Uani 1 1 d . . . . .
N5 N 0.1485(6) 0.3646(6) 0.8415(6) 0.053(3) Uani 1 1 d . . . . .
N6 N 0.2484(6) 0.5974(6) 0.2095(5) 0.042(3) Uani 1 1 d . . . . .
N7 N 0.3075(7) 0.4214(7) 0.3414(6) 0.050(3) Uani 1 1 d . . . . .
N8 N 0.3886(7) 0.5734(6) 0.3178(6) 0.054(3) Uani 1 1 d . . . . .
N9 N 0.3629(7) 0.4654(7) 0.2246(6) 0.058(3) Uani 1 1 d . . . . .
N10 N 0.3580(8) 0.4170(7) 0.1742(7) 0.070(4) Uani 1 1 d . . . . .
Ir2A Ir 0.270198 0.509017 0.234017 0.020 Uani 0.02 1 d . U P E 2
Ir1A Ir 0.232683 0.469154 0.780338 0.019 Uani 0.02 1 d . U P D 2


_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 C7 1.379(17) . ?
C1 C2 1.401(18) . ?
C1 Ir1A 1.936(13) . ?
C1 Ir1 2.034(13) . ?
C2 C3 1.378(19) . ?
C2 H2 0.9300 . ?
C3 C5 1.36(2) . ?
C3 C4 1.45(2) . ?
C4 F2 1.311(19) . ?
C4 F3 1.314(19) . ?
C4 F1 1.348(19) . ?
C5 C6 1.36(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.452(19) . ?
C8 N1 1.373(16) . ?
C8 C9 1.391(18) . ?
C9 C10 1.36(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.37(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.35(2) . ?
C11 H11 0.9300 . ?
C12 N1 1.311(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(18) . ?
C13 C19 1.433(19) . ?
C13 Ir1 2.035(13) . ?
C13 Ir1A 2.397(13) . ?
C14 C15 1.417(18) . ?
C14 H14 0.9300 . ?
C15 C17 1.37(2) . ?
C15 C16 1.51(3) . ?
C16 F6 1.26(2) . ?
C16 F4 1.27(2) . ?
C16 F5 1.32(2) . ?
C17 C18 1.39(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.37(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.41(2) . ?
C20 N2 1.352(18) . ?
C20 C21 1.36(2) . ?
C21 C22 1.37(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.36(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.41(2) . ?
C23 H23 0.9300 . ?
C24 N2 1.325(17) . ?
C24 Ir1A 2.364(15) . ?
C24 H24 0.9300 . ?
C25 N3 1.334(17) . ?
C25 C26 1.37(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.376(19) . ?
C26 H26 0.9300 . ?
C27 C28 1.39(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.380(19) . ?
C28 H28 0.9300 . ?
C29 N3 1.356(15) . ?
C29 C30 1.441(19) . ?
C30 N4 1.338(16) . ?
C30 C31 1.365(17) . ?
C31 C32 1.38(2) . ?
C31 H31 0.9300 . ?
C32 N5 1.369(16) . ?
C32 C33 1.487(19) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.420(17) . ?
C34 C40 1.435(18) . ?
C34 Ir2 1.988(12) . ?
C34 Ir2A 2.480(12) . ?
C35 C36 1.395(18) . ?
C35 H35 0.9300 . ?
C36 C38 1.38(2) . ?
C36 C37 1.51(2) . ?
C37 F9 1.28(2) . ?
C37 F7 1.31(2) . ?
C37 F8 1.32(2) . ?
C38 C39 1.36(2) . ?
C38 H38 0.9300 . ?
C39 C40 1.379(18) . ?
C39 H39 0.9300 . ?
C40 C41 1.458(19) . ?
C41 C42 1.373(19) . ?
C41 N6 1.386(16) . ?
C42 C43 1.37(2) . ?
C42 H42 0.9300 . ?
C43 C44 1.35(2) . ?
C43 H43 0.9300 . ?
C44 C45 1.38(2) . ?
C44 H44 0.9300 . ?
C45 N6 1.349(15) . ?
C45 Ir2A 2.379(14) . ?
C45 H45 0.9300 . ?
C46 C47 1.335(19) . ?
C46 C52 1.392(18) . ?
C46 Ir2A 1.846(13) . ?
C46 Ir2 2.047(14) . ?
C47 C48 1.41(2) . ?
C47 Ir2A 2.620(15) . ?
C47 H47 0.9300 . ?
C48 C50 1.37(2) . ?
C48 C49 1.49(2) . ?
C49 F10 1.23(2) . ?
C49 F11 1.29(2) . ?
C49 F12 1.32(2) . ?
C50 C51 1.38(2) . ?
C50 H50 0.9300 . ?
C51 C52 1.428(19) . ?
C51 H51 0.9300 . ?
C52 C53 1.472(19) . ?
C53 C54 1.367(18) . ?
C53 N7 1.385(17) . ?
C54 C55 1.35(2) . ?
C54 H54 0.9300 . ?
C55 C56 1.37(2) . ?
C55 H55 0.9300 . ?
C56 C57 1.397(19) . ?
C56 H56 0.9300 . ?
C57 N7 1.272(17) . ?
C57 H57 0.9300 . ?
C58 C59 1.35(2) . ?
C58 N8 1.379(17) . ?
C58 H58 0.9300 . ?
C59 C60 1.37(2) . ?
C59 H59 0.9300 . ?
C60 C61 1.34(2) . ?
C60 H60 0.9300 . ?
C61 C62 1.36(2) . ?
C61 H61 0.9300 . ?
C62 N8 1.336(15) . ?
C62 C63 1.41(2) . ?
C63 N9 1.364(18) . ?
C63 C64 1.43(2) . ?
C64 C65 1.38(2) . ?
C64 H64 0.9300 . ?
C65 N10 1.353(18) . ?
C65 C66 1.48(2) . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
Ir1 N1 2.043(10) . ?
Ir1 N2 2.052(12) . ?
Ir1 N4 2.103(9) . ?
Ir1 N3 2.144(11) . ?
Ir2 N6 2.016(10) . ?
Ir2 N7 2.023(11) . ?
Ir2 N9 2.106(11) . ?
Ir2 N8 2.160(11) . ?
N2 Ir1A 1.558(12) . ?
N3 Ir1A 2.495(12) . ?
N4 N5 1.357(14) . ?
N4 Ir1A 1.924(9) . ?
N6 Ir2A 1.602(10) . ?
N9 N10 1.329(16) . ?
N9 Ir2A 1.852(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
C7 C1 C2 118.0(13) . . ?
C7 C1 Ir1A 131.8(10) . . ?
C2 C1 Ir1A 108.7(10) . . ?
C7 C1 Ir1 114.5(10) . . ?
C2 C1 Ir1 127.5(10) . . ?
C3 C2 C1 119.0(13) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C5 C3 C2 123.0(16) . . ?
C5 C3 C4 116.7(15) . . ?
C2 C3 C4 120.3(15) . . ?
F2 C4 F3 103.1(16) . . ?
F2 C4 F1 102.3(16) . . ?
F3 C4 F1 101.5(16) . . ?
F2 C4 C3 117.1(16) . . ?
F3 C4 C3 116.5(16) . . ?
F1 C4 C3 114.2(15) . . ?
C6 C5 C3 118.9(14) . . ?
C6 C5 H5 120.6 . . ?
C3 C5 H5 120.6 . . ?
C5 C6 C7 120.0(14) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C1 C7 C6 121.0(14) . . ?
C1 C7 C8 115.9(12) . . ?
C6 C7 C8 122.9(13) . . ?
N1 C8 C9 119.9(14) . . ?
N1 C8 C7 114.2(11) . . ?
C9 C8 C7 126.0(13) . . ?
C10 C9 C8 119.4(15) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 118.7(15) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.4(17) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N1 C12 C11 122.3(15) . . ?
N1 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C14 C13 C19 118.9(13) . . ?
C14 C13 Ir1 127.7(11) . . ?
C19 C13 Ir1 113.4(10) . . ?
C14 C13 Ir1A 142.3(11) . . ?
C19 C13 Ir1A 98.5(10) . . ?
C13 C14 C15 120.0(14) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C17 C15 C14 120.4(16) . . ?
C17 C15 C16 121.4(16) . . ?
C14 C15 C16 118.0(17) . . ?
F6 C16 F4 109(2) . . ?
F6 C16 F5 101.4(19) . . ?
F4 C16 F5 106(2) . . ?
F6 C16 C15 113(2) . . ?
F4 C16 C15 117.0(16) . . ?
F5 C16 C15 109(2) . . ?
C15 C17 C18 119.7(17) . . ?
C15 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 121.3(18) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 124.7(16) . . ?
C18 C19 C13 119.7(15) . . ?
C20 C19 C13 115.6(13) . . ?
N2 C20 C21 120.9(16) . . ?
N2 C20 C19 115.4(13) . . ?
C21 C20 C19 123.6(16) . . ?
C20 C21 C22 120.0(19) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.5(19) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 118.6(18) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
N2 C24 C23 120.8(17) . . ?
N2 C24 Ir1A 38.3(7) . . ?
C23 C24 Ir1A 157.3(14) . . ?
N2 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
Ir1A C24 H24 82.0 . . ?
N3 C25 C26 125.2(13) . . ?
N3 C25 H25 117.4 . . ?
C26 C25 H25 117.4 . . ?
C25 C26 C27 116.3(15) . . ?
C25 C26 H26 121.9 . . ?
C27 C26 H26 121.9 . . ?
C26 C27 C28 120.2(15) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 C27 119.7(14) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
N3 C29 C28 120.3(13) . . ?
N3 C29 C30 114.8(12) . . ?
C28 C29 C30 124.9(12) . . ?
N4 C30 C31 109.4(13) . . ?
N4 C30 C29 116.4(11) . . ?
C31 C30 C29 134.0(14) . . ?
C30 C31 C32 105.5(14) . . ?
C30 C31 H31 127.3 . . ?
C32 C31 H31 127.3 . . ?
N5 C32 C31 109.5(12) . . ?
N5 C32 C33 119.7(14) . . ?
C31 C32 C33 130.9(15) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C40 114.8(12) . . ?
C35 C34 Ir2 130.1(10) . . ?
C40 C34 Ir2 115.1(9) . . ?
C35 C34 Ir2A 143.7(10) . . ?
C40 C34 Ir2A 100.6(9) . . ?
C36 C35 C34 121.8(14) . . ?
C36 C35 H35 119.1 . . ?
C34 C35 H35 119.1 . . ?
C38 C36 C35 120.2(14) . . ?
C38 C36 C37 120.5(14) . . ?
C35 C36 C37 119.3(15) . . ?
F9 C37 F7 109.2(19) . . ?
F9 C37 F8 107.1(18) . . ?
F7 C37 F8 105.4(15) . . ?
F9 C37 C36 114.9(14) . . ?
F7 C37 C36 107.8(16) . . ?
F8 C37 C36 112.0(16) . . ?
C39 C38 C36 120.3(14) . . ?
C39 C38 H38 119.9 . . ?
C36 C38 H38 119.9 . . ?
C38 C39 C40 120.6(15) . . ?
C38 C39 H39 119.7 . . ?
C40 C39 H39 119.7 . . ?
C39 C40 C34 122.3(14) . . ?
C39 C40 C41 123.6(14) . . ?
C34 C40 C41 114.1(12) . . ?
C42 C41 N6 120.9(14) . . ?
C42 C41 C40 125.7(14) . . ?
N6 C41 C40 113.5(12) . . ?
C41 C42 C43 119.9(16) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C44 C43 C42 119.4(17) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C43 C44 C45 120.0(16) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
N6 C45 C44 122.0(14) . . ?
N6 C45 Ir2A 40.0(6) . . ?
C44 C45 Ir2A 159.0(13) . . ?
N6 C45 H45 119.0 . . ?
C44 C45 H45 119.0 . . ?
Ir2A C45 H45 80.0 . . ?
C47 C46 C52 118.4(13) . . ?
C47 C46 Ir2A 109.9(10) . . ?
C52 C46 Ir2A 130.8(13) . . ?
C47 C46 Ir2 130.2(11) . . ?
C52 C46 Ir2 111.2(11) . . ?
C46 C47 C48 122.4(13) . . ?
C46 C47 Ir2A 41.5(7) . . ?
C48 C47 Ir2A 160.9(11) . . ?
C46 C47 H47 118.8 . . ?
C48 C47 H47 118.8 . . ?
Ir2A C47 H47 78.3 . . ?
C50 C48 C47 119.4(15) . . ?
C50 C48 C49 119.9(17) . . ?
C47 C48 C49 120.6(16) . . ?
F10 C49 F11 106(2) . . ?
F10 C49 F12 107.5(19) . . ?
F11 C49 F12 101.3(19) . . ?
F10 C49 C48 116.7(19) . . ?
F11 C49 C48 113.2(16) . . ?
F12 C49 C48 111.3(18) . . ?
C48 C50 C51 120.5(15) . . ?
C48 C50 H50 119.7 . . ?
C51 C50 H50 119.7 . . ?
C50 C51 C52 118.2(14) . . ?
C50 C51 H51 120.9 . . ?
C52 C51 H51 120.9 . . ?
C46 C52 C51 120.8(14) . . ?
C46 C52 C53 118.6(13) . . ?
C51 C52 C53 120.4(13) . . ?
C54 C53 N7 121.5(14) . . ?
C54 C53 C52 126.1(14) . . ?
N7 C53 C52 112.3(12) . . ?
C55 C54 C53 118.7(15) . . ?
C55 C54 H54 120.6 . . ?
C53 C54 H54 120.6 . . ?
C54 C55 C56 121.0(15) . . ?
C54 C55 H55 119.5 . . ?
C56 C55 H55 119.5 . . ?
C55 C56 C57 115.9(16) . . ?
C55 C56 H56 122.0 . . ?
C57 C56 H56 122.0 . . ?
N7 C57 C56 125.4(15) . . ?
N7 C57 H57 117.3 . . ?
C56 C57 H57 117.3 . . ?
C59 C58 N8 120.0(15) . . ?
C59 C58 H58 120.0 . . ?
N8 C58 H58 120.0 . . ?
C58 C59 C60 119.7(18) . . ?
C58 C59 H59 120.2 . . ?
C60 C59 H59 120.2 . . ?
C61 C60 C59 120.5(18) . . ?
C61 C60 H60 119.7 . . ?
C59 C60 H60 119.7 . . ?
C60 C61 C62 119.1(16) . . ?
C60 C61 H61 120.4 . . ?
C62 C61 H61 120.4 . . ?
N8 C62 C61 121.7(15) . . ?
N8 C62 C63 113.5(13) . . ?
C61 C62 C63 124.8(13) . . ?
N9 C63 C62 120.5(12) . . ?
N9 C63 C64 106.2(15) . . ?
C62 C63 C64 133.3(14) . . ?
C65 C64 C63 104.2(14) . . ?
C65 C64 H64 127.9 . . ?
C63 C64 H64 127.9 . . ?
N10 C65 C64 111.4(14) . . ?
N10 C65 C66 119.7(19) . . ?
C64 C65 C66 128.9(17) . . ?
C65 C66 H66A 109.5 . . ?
C65 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C65 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C1 Ir1 C13 92.2(5) . . ?
C1 Ir1 N1 79.9(5) . . ?
C13 Ir1 N1 96.9(5) . . ?
C1 Ir1 N2 95.6(5) . . ?
C13 Ir1 N2 79.4(6) . . ?
N1 Ir1 N2 174.1(4) . . ?
C1 Ir1 N4 98.1(4) . . ?
C13 Ir1 N4 167.4(5) . . ?
N1 Ir1 N4 92.1(4) . . ?
N2 Ir1 N4 92.3(4) . . ?
C1 Ir1 N3 171.2(5) . . ?
C13 Ir1 N3 94.8(5) . . ?
N1 Ir1 N3 93.9(4) . . ?
N2 Ir1 N3 90.9(4) . . ?
N4 Ir1 N3 75.6(4) . . ?
C34 Ir2 N6 80.8(5) . . ?
C34 Ir2 N7 95.1(5) . . ?
N6 Ir2 N7 175.1(4) . . ?
C34 Ir2 C46 91.0(5) . . ?
N6 Ir2 C46 95.4(5) . . ?
N7 Ir2 C46 81.8(6) . . ?
C34 Ir2 N9 171.0(5) . . ?
N6 Ir2 N9 92.6(4) . . ?
N7 Ir2 N9 91.7(4) . . ?
C46 Ir2 N9 95.7(5) . . ?
C34 Ir2 N8 97.2(5) . . ?
N6 Ir2 N8 89.7(4) . . ?
N7 Ir2 N8 93.5(5) . . ?
C46 Ir2 N8 170.9(5) . . ?
N9 Ir2 N8 76.5(5) . . ?
C12 N1 C8 119.3(12) . . ?
C12 N1 Ir1 125.2(9) . . ?
C8 N1 Ir1 115.4(9) . . ?
C24 N2 C20 119.7(14) . . ?
C24 N2 Ir1A 109.9(11) . . ?
C20 N2 Ir1A 130.0(11) . . ?
C24 N2 Ir1 124.0(11) . . ?
C20 N2 Ir1 116.1(10) . . ?
C25 N3 C29 118.0(12) . . ?
C25 N3 Ir1 125.9(9) . . ?
C29 N3 Ir1 115.9(9) . . ?
C25 N3 Ir1A 134.4(9) . . ?
C29 N3 Ir1A 106.4(9) . . ?
C30 N4 N5 109.4(10) . . ?
C30 N4 Ir1A 124.9(8) . . ?
N5 N4 Ir1A 117.7(8) . . ?
C30 N4 Ir1 117.2(8) . . ?
N5 N4 Ir1 132.4(8) . . ?
N4 N5 C32 106.2(11) . . ?
C45 N6 C41 117.6(12) . . ?
C45 N6 Ir2A 107.1(9) . . ?
C41 N6 Ir2A 132.4(9) . . ?
C45 N6 Ir2 125.9(9) . . ?
C41 N6 Ir2 116.5(8) . . ?
C57 N7 C53 117.2(13) . . ?
C57 N7 Ir2 126.8(10) . . ?
C53 N7 Ir2 115.8(10) . . ?
C62 N8 C58 118.9(13) . . ?
C62 N8 Ir2 116.2(10) . . ?
C58 N8 Ir2 124.9(9) . . ?
N10 N9 C63 111.6(11) . . ?
N10 N9 Ir2A 116.8(10) . . ?
C63 N9 Ir2A 124.8(10) . . ?
N10 N9 Ir2 134.7(10) . . ?
C63 N9 Ir2 113.2(10) . . ?
N9 N10 C65 106.6(14) . . ?
N6 Ir2A C46 121.2(6) . . ?
N6 Ir2A N9 119.2(5) . . ?
C46 Ir2A N9 112.7(6) . . ?
N6 Ir2A C45 32.8(5) . . ?
C46 Ir2A C45 125.9(7) . . ?
N9 Ir2A C45 92.7(5) . . ?
N6 Ir2A C34 75.6(5) . . ?
C46 Ir2A C34 82.0(5) . . ?
N9 Ir2A C34 140.3(5) . . ?
C45 Ir2A C34 108.4(5) . . ?
N6 Ir2A C47 97.9(5) . . ?
C46 Ir2A C47 28.6(5) . . ?
N9 Ir2A C47 119.9(5) . . ?
C45 Ir2A C47 97.2(5) . . ?
C34 Ir2A C47 91.1(4) . . ?
N2 Ir1A N4 118.4(5) . . ?
N2 Ir1A C1 119.8(6) . . ?
N4 Ir1A C1 108.2(5) . . ?
N2 Ir1A C24 31.8(6) . . ?
N4 Ir1A C24 90.2(5) . . ?
C1 Ir1A C24 123.2(6) . . ?
N2 Ir1A C13 79.5(6) . . ?
N4 Ir1A C13 144.0(5) . . ?
C1 Ir1A C13 84.5(5) . . ?
C24 Ir1A C13 111.3(6) . . ?
N2 Ir1A N3 92.2(5) . . ?
N4 Ir1A N3 70.9(4) . . ?
C1 Ir1A N3 139.9(5) . . ?
C24 Ir1A N3 96.9(5) . . ?
C13 Ir1A N3 77.9(4) . . ?

_refine_diff_density_max         2.134
_refine_diff_density_min         -1.699
_refine_diff_density_rms         0.169



####################################################################### 
# 
# 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_111_a
_database_code_depnum_ccdc_archive 'CCDC 1821899'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H19 F9 Ir N5'
_chemical_formula_weight         848.73

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'
S S 0.1246 0.1234 '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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2965(12)
_cell_length_b                   16.5703(15)
_cell_length_c                   14.9226(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.0370(10)
_cell_angle_gamma                90
_cell_volume                     3002.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9855
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.49
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_F_000             1640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    4.536
_shelx_estimated_absorpt_T_min   0.374
_shelx_estimated_absorpt_T_max   0.435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5642
_exptl_absorpt_correction_T_max  0.7269
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22054
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5296
_reflns_number_gt                4823
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0527P)²+2.9904P] 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         5296
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.3935(5) 0.1711(4) 0.8040(4) 0.0507(16) Uani 1 1 d . . . . .
C2 C 0.4492(4) 0.1565(4) 0.7240(3) 0.0365(12) Uani 1 1 d . . . . .
C3 C 0.5154(5) 0.0892(4) 0.7212(4) 0.0446(14) Uani 1 1 d . . . . .
H3 H 0.526141 0.052972 0.769415 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5649(4) 0.0768(3) 0.6462(4) 0.0401(13) Uani 1 1 d . . . . .
H4 H 0.609163 0.031594 0.643551 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5496(4) 0.1309(3) 0.5740(3) 0.0255(10) Uani 1 1 d . . . . .
C6 C 0.4825(3) 0.1999(3) 0.5758(3) 0.0194(9) Uani 1 1 d . . . . .
C7 C 0.4329(4) 0.2106(3) 0.6524(3) 0.0238(9) Uani 1 1 d . . . . .
H7 H 0.387665 0.255141 0.655727 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5992(3) 0.1212(3) 0.4911(3) 0.0276(10) Uani 1 1 d . . . . .
C9 C 0.6685(4) 0.0593(3) 0.4746(4) 0.0422(13) Uani 1 1 d . . . . .
H9 H 0.686967 0.019156 0.517880 0.051 Uiso 1 1 calc R U . . .
C10 C 0.7109(4) 0.0569(4) 0.3938(4) 0.0491(15) Uani 1 1 d . . . . .
H10 H 0.756423 0.014702 0.381897 0.059 Uiso 1 1 calc R U . . .
C11 C 0.6846(4) 0.1172(4) 0.3321(4) 0.0422(13) Uani 1 1 d . . . . .
H11 H 0.712089 0.116612 0.277544 0.051 Uiso 1 1 calc R U . . .
C12 C 0.6167(4) 0.1793(3) 0.3513(3) 0.0303(11) Uani 1 1 d . . . . .
H12 H 0.600670 0.221116 0.309754 0.036 Uiso 1 1 calc R U . . .
C13 C 0.8925(3) 0.3826(3) 0.5972(3) 0.0259(10) Uani 1 1 d . . . . .
C14 C 0.7691(3) 0.3911(3) 0.5840(3) 0.0201(9) Uani 1 1 d . . . . .
C15 C 0.7274(3) 0.4563(3) 0.6254(3) 0.0230(9) Uani 1 1 d . . . . .
H15 H 0.774561 0.493685 0.657796 0.028 Uiso 1 1 calc R U . . .
C16 C 0.6153(3) 0.4650(3) 0.6179(3) 0.0200(9) Uani 1 1 d . . . . .
H16 H 0.585701 0.508459 0.645292 0.024 Uiso 1 1 calc R U . . .
C17 C 0.5459(3) 0.4081(2) 0.5690(3) 0.0147(8) Uani 1 1 d . . . . .
C18 C 0.5865(3) 0.3423(3) 0.5252(3) 0.0152(8) Uani 1 1 d . . . . .
C19 C 0.7012(3) 0.3353(3) 0.5335(3) 0.0179(8) Uani 1 1 d . . . . .
H19 H 0.731896 0.293094 0.504905 0.022 Uiso 1 1 calc R U . . .
C20 C 0.4245(3) 0.4122(2) 0.5613(2) 0.0155(8) Uani 1 1 d . . . . .
C21 C 0.3675(3) 0.4702(3) 0.6025(3) 0.0214(9) Uani 1 1 d . . . . .
H21 H 0.405165 0.511043 0.637109 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2531(4) 0.4664(3) 0.5911(3) 0.0275(10) Uani 1 1 d . . . . .
H22 H 0.213430 0.504168 0.618864 0.033 Uiso 1 1 calc R U . . .
C23 C 0.1992(3) 0.4058(3) 0.5381(3) 0.0268(10) Uani 1 1 d . . . . .
H23 H 0.122783 0.402725 0.529277 0.032 Uiso 1 1 calc R U . . .
C24 C 0.2594(3) 0.3504(3) 0.4988(3) 0.0216(9) Uani 1 1 d . . . . .
H24 H 0.222613 0.309761 0.463191 0.026 Uiso 1 1 calc R U . . .
C25 C 0.5047(4) 0.4185(3) 0.1347(3) 0.0306(11) Uani 1 1 d . . . . .
C26 C 0.4544(4) 0.3725(3) 0.2022(3) 0.0211(9) Uani 1 1 d . . . . .
C27 C 0.3582(4) 0.3280(3) 0.1890(3) 0.0233(9) Uani 1 1 d . . . . .
H27 H 0.307478 0.322086 0.136211 0.028 Uiso 1 1 calc R U . . .
C28 C 0.2857(4) 0.2349(2) 0.3086(3) 0.0206(9) Uani 1 1 d . . . . .
C29 C 0.1834(4) 0.2102(3) 0.2635(3) 0.0242(10) Uani 1 1 d . . . . .
H29 H 0.155867 0.231056 0.206621 0.029 Uiso 1 1 calc R U . . .
C30 C 0.1232(4) 0.1548(3) 0.3038(3) 0.0300(11) Uani 1 1 d . . . . .
H30 H 0.054591 0.138067 0.274427 0.036 Uiso 1 1 calc R U . . .
C31 C 0.1655(4) 0.1240(3) 0.3884(3) 0.0307(10) Uani 1 1 d . . . . .
H31 H 0.126396 0.086068 0.416426 0.037 Uiso 1 1 calc R U . . .
C32 C 0.2672(3) 0.1511(3) 0.4301(3) 0.0242(9) Uani 1 1 d . . . . .
H32 H 0.295629 0.130767 0.487083 0.029 Uiso 1 1 calc R U . . .
C33 C 0.3558(3) 0.2943(3) 0.2737(3) 0.0176(8) Uani 1 1 d . . . . .
F1 F 0.3903(6) 0.2458(3) 0.8283(4) 0.0937(19) Uani 1 1 d . . . . .
F2 F 0.4323(4) 0.1245(3) 0.8741(2) 0.0951(16) Uani 1 1 d . . . . .
F3 F 0.2878(4) 0.1472(4) 0.7882(3) 0.113(2) Uani 1 1 d . . . . .
F4 F 0.9371(2) 0.3797(2) 0.6847(2) 0.0443(8) Uani 1 1 d . . . . .
F5 F 0.9407(2) 0.44640(19) 0.5628(2) 0.0419(7) Uani 1 1 d . . . . .
F6 F 0.9276(2) 0.31754(18) 0.5582(2) 0.0380(7) Uani 1 1 d . . . . .
F7 F 0.5388(3) 0.49260(18) 0.16369(19) 0.0425(7) Uani 1 1 d . . . . .
F8 F 0.5953(3) 0.3831(2) 0.1120(2) 0.0500(8) Uani 1 1 d . . . . .
F9 F 0.4356(3) 0.4300(2) 0.05738(19) 0.0506(9) Uani 1 1 d . . . . .
Ir01 Ir 0.46835(2) 0.26778(2) 0.46213(2) 0.01349(9) Uani 1 1 d . . . . .
N1 N 0.5730(3) 0.1809(2) 0.4292(2) 0.0223(8) Uani 1 1 d . . . . .
N2 N 0.3714(3) 0.3527(2) 0.5101(2) 0.0152(7) Uani 1 1 d . . . . .
N3 N 0.3268(3) 0.2054(2) 0.3924(2) 0.0177(7) Uani 1 1 d . . . . .
N4 N 0.4456(3) 0.3196(2) 0.3319(2) 0.0168(7) Uani 1 1 d . . . . .
N5 N 0.5079(3) 0.3680(2) 0.2886(2) 0.0202(7) 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
C1 F1 1.293(8) . ?
C1 F2 1.327(7) . ?
C1 F3 1.344(8) . ?
C1 C2 1.486(8) . ?
C2 C3 1.386(8) . ?
C2 C7 1.385(7) . ?
C3 C4 1.370(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(6) . ?
C5 C8 1.471(7) . ?
C6 C7 1.390(6) . ?
C6 Ir01 2.020(4) . ?
C7 H7 0.9300 . ?
C8 N1 1.358(6) . ?
C8 C9 1.379(7) . ?
C9 C10 1.387(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(7) . ?
C11 H11 0.9300 . ?
C12 N1 1.354(6) . ?
C12 H12 0.9300 . ?
C13 F6 1.330(6) . ?
C13 F4 1.336(5) . ?
C13 F5 1.351(5) . ?
C13 C14 1.505(6) . ?
C14 C15 1.383(6) . ?
C14 C19 1.386(6) . ?
C15 C16 1.373(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(6) . ?
C17 C20 1.480(5) . ?
C18 C19 1.401(5) . ?
C18 Ir01 2.023(4) . ?
C19 H19 0.9300 . ?
C20 N2 1.351(5) . ?
C20 C21 1.388(6) . ?
C21 C22 1.391(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(6) . ?
C23 H23 0.9300 . ?
C24 N2 1.361(5) . ?
C24 H24 0.9300 . ?
C25 F9 1.335(5) . ?
C25 F8 1.350(6) . ?
C25 F7 1.347(6) . ?
C25 C26 1.473(6) . ?
C26 N5 1.354(5) . ?
C26 C27 1.381(6) . ?
C27 C33 1.386(6) . ?
C27 H27 0.9300 . ?
C28 N3 1.364(6) . ?
C28 C29 1.391(6) . ?
C28 C33 1.457(6) . ?
C29 C30 1.376(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.384(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.382(6) . ?
C31 H31 0.9300 . ?
C32 N3 1.338(6) . ?
C32 H32 0.9300 . ?
C33 N4 1.361(5) . ?
Ir01 N1 2.043(4) . ?
Ir01 N2 2.045(3) . ?
Ir01 N4 2.102(3) . ?
Ir01 N3 2.148(3) . ?
N4 N5 1.342(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
F1 C1 F2 111.1(6) . . ?
F1 C1 F3 105.1(6) . . ?
F2 C1 F3 100.6(5) . . ?
F1 C1 C2 114.8(5) . . ?
F2 C1 C2 112.6(6) . . ?
F3 C1 C2 111.5(5) . . ?
C3 C2 C7 120.8(5) . . ?
C3 C2 C1 120.2(5) . . ?
C7 C2 C1 119.0(5) . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 121.0(5) . . ?
C4 C5 C8 123.8(5) . . ?
C6 C5 C8 115.2(4) . . ?
C7 C6 C5 116.9(4) . . ?
C7 C6 Ir01 128.9(3) . . ?
C5 C6 Ir01 114.1(3) . . ?
C2 C7 C6 121.5(5) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N1 C8 C9 120.5(5) . . ?
N1 C8 C5 114.0(4) . . ?
C9 C8 C5 125.5(5) . . ?
C8 C9 C10 120.2(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 119.5(5) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N1 C12 C11 121.7(5) . . ?
N1 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
F6 C13 F4 106.6(4) . . ?
F6 C13 F5 106.1(4) . . ?
F4 C13 F5 105.2(4) . . ?
F6 C13 C14 114.1(4) . . ?
F4 C13 C14 112.4(4) . . ?
F5 C13 C14 111.8(4) . . ?
C15 C14 C19 122.0(4) . . ?
C15 C14 C13 116.8(4) . . ?
C19 C14 C13 121.2(4) . . ?
C16 C15 C14 118.9(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 119.7(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 122.3(4) . . ?
C16 C17 C20 122.3(4) . . ?
C18 C17 C20 115.3(3) . . ?
C19 C18 C17 116.7(4) . . ?
C19 C18 Ir01 129.1(3) . . ?
C17 C18 Ir01 114.1(3) . . ?
C14 C19 C18 120.4(4) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N2 C20 C21 121.5(4) . . ?
N2 C20 C17 113.7(3) . . ?
C21 C20 C17 124.8(4) . . ?
C20 C21 C22 119.1(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 119.2(4) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C24 C23 C22 119.4(4) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
N2 C24 C23 122.2(4) . . ?
N2 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
F9 C25 F8 106.4(4) . . ?
F9 C25 F7 105.7(4) . . ?
F8 C25 F7 104.4(4) . . ?
F9 C25 C26 112.7(4) . . ?
F8 C25 C26 113.5(4) . . ?
F7 C25 C26 113.3(4) . . ?
N5 C26 C27 112.5(4) . . ?
N5 C26 C25 119.0(4) . . ?
C27 C26 C25 128.4(4) . . ?
C26 C27 C33 103.0(4) . . ?
C26 C27 H27 128.5 . . ?
C33 C27 H27 128.5 . . ?
N3 C28 C29 120.9(4) . . ?
N3 C28 C33 114.5(4) . . ?
C29 C28 C33 124.5(4) . . ?
C30 C29 C28 119.5(4) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C31 C30 C29 119.6(4) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C32 118.3(5) . . ?
C30 C31 H31 120.8 . . ?
C32 C31 H31 120.8 . . ?
N3 C32 C31 123.0(4) . . ?
N3 C32 H32 118.5 . . ?
C31 C32 H32 118.5 . . ?
N4 C33 C27 109.1(4) . . ?
N4 C33 C28 116.5(4) . . ?
C27 C33 C28 134.1(4) . . ?
C6 Ir01 C18 89.35(16) . . ?
C6 Ir01 N1 80.50(16) . . ?
C18 Ir01 N1 96.23(15) . . ?
C6 Ir01 N2 93.87(15) . . ?
C18 Ir01 N2 80.36(14) . . ?
N1 Ir01 N2 173.49(13) . . ?
C6 Ir01 N4 170.05(15) . . ?
C18 Ir01 N4 99.31(14) . . ?
N1 Ir01 N4 93.60(14) . . ?
N2 Ir01 N4 92.43(13) . . ?
C6 Ir01 N3 95.47(14) . . ?
C18 Ir01 N3 170.94(15) . . ?
N1 Ir01 N3 92.14(13) . . ?
N2 Ir01 N3 91.63(13) . . ?
N4 Ir01 N3 76.64(13) . . ?
C12 N1 C8 119.1(4) . . ?
C12 N1 Ir01 124.7(3) . . ?
C8 N1 Ir01 116.2(3) . . ?
C20 N2 C24 118.7(4) . . ?
C20 N2 Ir01 116.3(2) . . ?
C24 N2 Ir01 124.8(3) . . ?
C32 N3 C28 118.6(4) . . ?
C32 N3 Ir01 125.1(3) . . ?
C28 N3 Ir01 115.3(3) . . ?
N5 N4 C33 110.1(3) . . ?
N5 N4 Ir01 133.3(2) . . ?
C33 N4 Ir01 116.2(3) . . ?
N4 N5 C26 105.3(3) . . ?

_refine_diff_density_max         2.437
_refine_diff_density_min         -2.281
_refine_diff_density_rms         0.236



