# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_160522f
_database_code_depnum_ccdc_archive 'CCDC 1569665'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H33 Cl F6 Ir N2 O2 P'
_chemical_formula_weight         862.23

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.0370(9)
_cell_length_b                   19.4409(15)
_cell_length_c                   16.9061(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.8730(10)
_cell_angle_gamma                90.00
_cell_volume                     3294.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2978
_cell_measurement_theta_min      2.286
_cell_measurement_theta_max      21.195

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    4.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4690
_exptl_absorpt_correction_T_max  0.6296
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16339
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_unetI/netI     0.1013
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5794
_reflns_number_gt                3342
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0755P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5794
_refine_ls_number_parameters     439
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1499
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.66997(4) 0.20728(2) 0.46271(2) 0.04512(18) Uani 1 1 d . . .
Cl1 Cl 0.7208(9) 0.1157(6) 0.3892(5) 0.073(2) Uani 0.436(8) 1 d P A 1
Cl2 Cl 0.7214(13) 0.0735(8) 0.4102(7) 0.073(2) Uani 0.314(8) 1 d P A 2
Cl3 Cl 0.7230(13) 0.1386(7) 0.3192(7) 0.073(2) Uani 0.250(5) 1 d P A 3
P1 P 0.2007(3) 0.3249(2) 0.2103(2) 0.0679(10) Uani 1 1 d . . .
N2 N 0.4765(8) 0.1672(5) 0.4489(5) 0.047(2) Uani 1 1 d . A .
N1 N 0.6630(8) 0.1362(5) 0.5545(5) 0.049(2) Uani 1 1 d . A .
F1 F 0.1200(9) 0.2529(5) 0.2079(5) 0.110(3) Uani 1 1 d . . .
F2 F 0.2787(10) 0.3935(5) 0.2131(6) 0.139(4) Uani 1 1 d . . .
F3 F 0.1953(9) 0.3259(5) 0.3036(5) 0.117(3) Uani 1 1 d . . .
F4 F 0.3360(9) 0.2820(5) 0.2199(6) 0.128(4) Uani 1 1 d . . .
F5 F 0.2119(9) 0.3177(5) 0.1184(5) 0.120(3) Uani 1 1 d . . .
F6 F 0.0643(8) 0.3622(5) 0.2029(6) 0.123(3) Uani 1 1 d . . .
O1 O 0.1129(8) 0.0726(5) 0.4221(5) 0.082(3) Uani 1 1 d . . .
O2 O 0.6289(8) 0.0015(4) 0.7401(4) 0.069(2) Uani 1 1 d . A .
C1 C 0.6284(11) 0.3163(6) 0.4822(7) 0.058(3) Uani 1 1 d . A .
C2 C 0.7429(11) 0.2956(6) 0.5323(7) 0.057(3) Uani 1 1 d . A .
C3 C 0.8445(11) 0.2727(6) 0.4823(7) 0.059(3) Uani 1 1 d . A .
C4 C 0.7963(11) 0.2808(6) 0.4038(7) 0.060(3) Uani 1 1 d . A .
C5 C 0.6646(11) 0.3055(6) 0.4006(7) 0.062(3) Uani 1 1 d . A .
C6 C 0.5020(11) 0.3458(6) 0.5086(7) 0.059(3) Uani 1 1 d . . .
C7 C 0.4575(13) 0.4082(7) 0.4768(8) 0.075(4) Uani 1 1 d . A .
H7 H 0.5044 0.4292 0.4374 0.090 Uiso 1 1 calc R . .
C8 C 0.3439(13) 0.4392(7) 0.5035(9) 0.082(4) Uani 1 1 d . . .
H8 H 0.3141 0.4800 0.4800 0.099 Uiso 1 1 calc R A .
C9 C 0.2749(14) 0.4120(8) 0.5625(10) 0.079(4) Uani 1 1 d . A .
C10 C 0.3187(13) 0.3492(7) 0.5920(9) 0.077(4) Uani 1 1 d . . .
H10 H 0.2711 0.3284 0.6314 0.092 Uiso 1 1 calc R A .
C11 C 0.4275(12) 0.3165(7) 0.5664(8) 0.065(3) Uani 1 1 d . A .
H11 H 0.4524 0.2741 0.5879 0.079 Uiso 1 1 calc R . .
C12 C 0.1588(16) 0.4481(9) 0.5922(11) 0.093(5) Uani 1 1 d . . .
C13 C 0.1282(17) 0.5154(9) 0.5734(11) 0.109(5) Uani 1 1 d . A .
H13 H 0.1818 0.5380 0.5384 0.130 Uiso 1 1 calc R . .
C14 C 0.0253(18) 0.5507(10) 0.6025(12) 0.115(6) Uani 1 1 d . . .
H14 H 0.0111 0.5968 0.5898 0.138 Uiso 1 1 calc R A .
C15 C -0.0538(18) 0.5179(11) 0.6492(12) 0.117(6) Uani 1 1 d . A .
H15 H -0.1286 0.5411 0.6657 0.140 Uiso 1 1 calc R . .
C16 C -0.0341(18) 0.4521(11) 0.6753(13) 0.131(7) Uani 1 1 d . . .
H16 H -0.0891 0.4309 0.7106 0.157 Uiso 1 1 calc R A .
C17 C 0.0820(17) 0.4174(9) 0.6426(11) 0.114(6) Uani 1 1 d . A .
H17 H 0.1016 0.3725 0.6580 0.137 Uiso 1 1 calc R . .
C18 C 0.7510(13) 0.3009(7) 0.6212(7) 0.072(4) Uani 1 1 d . . .
H18A H 0.7826 0.2582 0.6435 0.108 Uiso 1 1 calc R A .
H18B H 0.6641 0.3108 0.6396 0.108 Uiso 1 1 calc R . .
H18C H 0.8114 0.3372 0.6372 0.108 Uiso 1 1 calc R . .
C19 C 0.9824(11) 0.2537(8) 0.5096(8) 0.082(4) Uani 1 1 d . . .
H19A H 1.0382 0.2938 0.5097 0.123 Uiso 1 1 calc R A .
H19B H 1.0164 0.2198 0.4746 0.123 Uiso 1 1 calc R . .
H19C H 0.9819 0.2352 0.5622 0.123 Uiso 1 1 calc R . .
C20 C 0.8758(13) 0.2685(8) 0.3342(8) 0.091(5) Uani 1 1 d . . .
H20A H 0.9279 0.2275 0.3423 0.136 Uiso 1 1 calc R A .
H20B H 0.9341 0.3069 0.3270 0.136 Uiso 1 1 calc R . .
H20C H 0.8172 0.2632 0.2879 0.136 Uiso 1 1 calc R . .
C21 C 0.5830(12) 0.3257(7) 0.3274(7) 0.077(4) Uani 1 1 d . . .
H21A H 0.6275 0.3619 0.3006 0.116 Uiso 1 1 calc R A .
H21B H 0.4969 0.3414 0.3420 0.116 Uiso 1 1 calc R . .
H21C H 0.5723 0.2867 0.2929 0.116 Uiso 1 1 calc R . .
C22 C 0.3896(11) 0.1837(6) 0.3891(7) 0.059(3) Uani 1 1 d . . .
H22 H 0.4145 0.2171 0.3534 0.070 Uiso 1 1 calc R A .
C23 C 0.2668(10) 0.1543(6) 0.3776(7) 0.056(3) Uani 1 1 d . A .
H23 H 0.2084 0.1677 0.3360 0.067 Uiso 1 1 calc R . .
C24 C 0.2327(11) 0.1034(6) 0.4306(7) 0.059(3) Uani 1 1 d . A .
C25 C 0.3205(10) 0.0864(6) 0.4930(6) 0.048(3) Uani 1 1 d . . .
H25 H 0.2972 0.0535 0.5299 0.058 Uiso 1 1 calc R . .
C26 C 0.4419(9) 0.1181(6) 0.5001(6) 0.044(3) Uani 1 1 d . A .
C27 C 0.5460(10) 0.1018(6) 0.5622(6) 0.048(3) Uani 1 1 d . . .
C28 C 0.5311(10) 0.0554(6) 0.6222(6) 0.047(3) Uani 1 1 d . A .
H28 H 0.4508 0.0319 0.6256 0.057 Uiso 1 1 calc R . .
C29 C 0.6339(11) 0.0432(6) 0.6775(7) 0.056(3) Uani 1 1 d . . .
C30 C 0.7553(11) 0.0773(6) 0.6680(7) 0.060(3) Uani 1 1 d . A .
H30 H 0.8279 0.0700 0.7034 0.072 Uiso 1 1 calc R . .
C31 C 0.7639(10) 0.1204(6) 0.6068(6) 0.052(3) Uani 1 1 d . . .
H31 H 0.8461 0.1411 0.5999 0.063 Uiso 1 1 calc R A .
C32 C 0.053(2) 0.0362(13) 0.4815(14) 0.066(7) Uani 0.50 1 d P . 1
H32A H 0.1065 0.0377 0.5300 0.099 Uiso 0.50 1 d PR . 1
H32B H -0.0337 0.0553 0.4901 0.099 Uiso 0.50 1 d PR . 1
H32C H 0.0425 -0.0107 0.4643 0.099 Uiso 0.50 1 d PR . 1
C32' C 0.037(2) 0.0718(14) 0.3505(14) 0.075(8) Uani 0.50 1 d P . 2
H32D H -0.0202 0.0323 0.3489 0.112 Uiso 0.50 1 calc PR . 2
H32E H 0.0958 0.0697 0.3074 0.112 Uiso 0.50 1 calc PR . 2
H32F H -0.0156 0.1129 0.3461 0.112 Uiso 0.50 1 calc PR . 2
C33 C 0.5061(13) -0.0309(7) 0.7560(7) 0.087(5) Uani 1 1 d . . .
H33A H 0.4403 0.0035 0.7654 0.130 Uiso 1 1 calc R A .
H33B H 0.5184 -0.0597 0.8019 0.130 Uiso 1 1 calc R . .
H33C H 0.4767 -0.0584 0.7113 0.130 Uiso 1 1 calc R . .


_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 N1 2.082(9) . ?
Ir1 N2 2.095(8) . ?
Ir1 C3 2.177(11) . ?
Ir1 C5 2.179(12) . ?
Ir1 C4 2.184(10) . ?
Ir1 C2 2.187(11) . ?
Ir1 C1 2.189(12) . ?
Ir1 Cl1 2.244(10) . ?
Ir1 Cl2 2.805(15) . ?
Ir1 Cl3 2.843(12) . ?
P1 F2 1.546(10) . ?
P1 F6 1.549(8) . ?
P1 F5 1.569(8) . ?
P1 F3 1.582(8) . ?
P1 F4 1.595(9) . ?
P1 F1 1.617(9) . ?
N2 C22 1.341(13) . ?
N2 C26 1.346(13) . ?
N1 C31 1.347(12) . ?
N1 C27 1.363(12) . ?
O1 C24 1.345(13) . ?
O1 C32 1.39(2) . ?
O1 C32' 1.39(2) . ?
O2 C29 1.336(13) . ?
O2 C33 1.421(13) . ?
C1 C2 1.450(15) . ?
C1 C5 1.459(16) . ?
C1 C6 1.482(16) . ?
C2 C3 1.428(16) . ?
C2 C18 1.504(15) . ?
C3 C4 1.399(16) . ?
C3 C19 1.484(15) . ?
C4 C5 1.404(16) . ?
C4 C20 1.474(16) . ?
C5 C21 1.501(15) . ?
C6 C11 1.383(16) . ?
C6 C7 1.390(16) . ?
C7 C8 1.385(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.351(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(18) . ?
C9 C12 1.47(2) . ?
C10 C11 1.354(16) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.32(2) . ?
C12 C13 1.38(2) . ?
C13 C14 1.35(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.31(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.36(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.48(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.363(15) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(15) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(14) . ?
C25 C26 1.366(13) . ?
C25 H25 0.9300 . ?
C26 C27 1.477(14) . ?
C27 C28 1.371(14) . ?
C28 C29 1.378(14) . ?
C28 H28 0.9300 . ?
C29 C30 1.403(15) . ?
C30 C31 1.337(14) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C32 1.88(4) 3_556 ?
C32 H32A 0.9600 . ?
C32 H32B 0.9599 . ?
C32 H32C 0.9601 . ?
C32' H32D 0.9600 . ?
C32' H32E 0.9600 . ?
C32' H32F 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?

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
N1 Ir1 N2 76.7(3) . . ?
N1 Ir1 C3 109.4(4) . . ?
N2 Ir1 C3 165.7(4) . . ?
N1 Ir1 C5 160.1(4) . . ?
N2 Ir1 C5 105.8(4) . . ?
C3 Ir1 C5 64.0(4) . . ?
N1 Ir1 C4 144.7(4) . . ?
N2 Ir1 C4 138.5(4) . . ?
C3 Ir1 C4 37.4(4) . . ?
C5 Ir1 C4 37.5(4) . . ?
N1 Ir1 C2 98.2(4) . . ?
N2 Ir1 C2 129.5(4) . . ?
C3 Ir1 C2 38.2(4) . . ?
C5 Ir1 C2 64.6(5) . . ?
C4 Ir1 C2 62.9(4) . . ?
N1 Ir1 C1 121.2(4) . . ?
N2 Ir1 C1 101.2(4) . . ?
C3 Ir1 C1 64.5(4) . . ?
C5 Ir1 C1 39.0(4) . . ?
C4 Ir1 C1 63.5(4) . . ?
C2 Ir1 C1 38.7(4) . . ?
N1 Ir1 Cl1 84.4(4) . . ?
N2 Ir1 Cl1 83.0(3) . . ?
C3 Ir1 Cl1 110.1(4) . . ?
C5 Ir1 Cl1 115.4(4) . . ?
C4 Ir1 Cl1 96.5(4) . . ?
C2 Ir1 Cl1 147.3(4) . . ?
C1 Ir1 Cl1 154.4(4) . . ?
N1 Ir1 Cl2 68.5(4) . . ?
N2 Ir1 Cl2 78.7(4) . . ?
C3 Ir1 Cl2 115.5(4) . . ?
C5 Ir1 Cl2 131.4(4) . . ?
C4 Ir1 Cl2 110.0(4) . . ?
C2 Ir1 Cl2 146.8(4) . . ?
C1 Ir1 Cl2 170.2(4) . . ?
Cl1 Ir1 Cl2 16.0(3) . . ?
N1 Ir1 Cl3 109.8(4) . . ?
N2 Ir1 Cl3 86.7(3) . . ?
C3 Ir1 Cl3 102.7(4) . . ?
C5 Ir1 Cl3 90.1(4) . . ?
C4 Ir1 Cl3 77.3(4) . . ?
C2 Ir1 Cl3 139.1(4) . . ?
C1 Ir1 Cl3 128.9(4) . . ?
Cl1 Ir1 Cl3 25.5(4) . . ?
Cl2 Ir1 Cl3 41.3(4) . . ?
F2 P1 F6 92.4(6) . . ?
F2 P1 F5 92.7(6) . . ?
F6 P1 F5 93.9(6) . . ?
F2 P1 F3 90.1(6) . . ?
F6 P1 F3 90.0(5) . . ?
F5 P1 F3 175.1(6) . . ?
F2 P1 F4 91.2(6) . . ?
F6 P1 F4 176.1(6) . . ?
F5 P1 F4 87.3(5) . . ?
F3 P1 F4 88.6(5) . . ?
F2 P1 F1 179.5(7) . . ?
F6 P1 F1 87.9(5) . . ?
F5 P1 F1 87.7(5) . . ?
F3 P1 F1 89.6(5) . . ?
F4 P1 F1 88.4(5) . . ?
C22 N2 C26 118.4(9) . . ?
C22 N2 Ir1 124.0(7) . . ?
C26 N2 Ir1 117.4(7) . . ?
C31 N1 C27 116.6(9) . . ?
C31 N1 Ir1 126.1(7) . . ?
C27 N1 Ir1 117.2(7) . . ?
C24 O1 C32 124.6(12) . . ?
C24 O1 C32' 122.9(13) . . ?
C32 O1 C32' 112.5(15) . . ?
C29 O2 C33 119.1(9) . . ?
C2 C1 C5 106.5(10) . . ?
C2 C1 C6 126.7(11) . . ?
C5 C1 C6 126.8(11) . . ?
C2 C1 Ir1 70.6(7) . . ?
C5 C1 Ir1 70.1(7) . . ?
C6 C1 Ir1 126.4(8) . . ?
C3 C2 C1 108.0(10) . . ?
C3 C2 C18 127.5(10) . . ?
C1 C2 C18 124.4(11) . . ?
C3 C2 Ir1 70.5(7) . . ?
C1 C2 Ir1 70.7(7) . . ?
C18 C2 Ir1 126.2(8) . . ?
C4 C3 C2 107.6(10) . . ?
C4 C3 C19 126.7(11) . . ?
C2 C3 C19 125.1(11) . . ?
C4 C3 Ir1 71.6(6) . . ?
C2 C3 Ir1 71.3(6) . . ?
C19 C3 Ir1 129.3(9) . . ?
C3 C4 C5 110.8(10) . . ?
C3 C4 C20 124.3(11) . . ?
C5 C4 C20 124.8(12) . . ?
C3 C4 Ir1 71.0(6) . . ?
C5 C4 Ir1 71.0(6) . . ?
C20 C4 Ir1 127.5(9) . . ?
C4 C5 C1 107.0(10) . . ?
C4 C5 C21 126.5(11) . . ?
C1 C5 C21 126.1(11) . . ?
C4 C5 Ir1 71.4(7) . . ?
C1 C5 Ir1 70.9(6) . . ?
C21 C5 Ir1 128.7(9) . . ?
C11 C6 C7 117.3(12) . . ?
C11 C6 C1 123.7(12) . . ?
C7 C6 C1 118.9(11) . . ?
C8 C7 C6 120.5(13) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 122.0(14) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 116.6(14) . . ?
C8 C9 C12 120.6(15) . . ?
C10 C9 C12 122.8(15) . . ?
C11 C10 C9 123.1(14) . . ?
C11 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C10 C11 C6 120.4(13) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C17 C12 C13 116.6(17) . . ?
C17 C12 C9 120.2(17) . . ?
C13 C12 C9 123.1(17) . . ?
C14 C13 C12 124.3(19) . . ?
C14 C13 H13 117.9 . . ?
C12 C13 H13 117.9 . . ?
C15 C14 C13 118(2) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C16 125(2) . . ?
C14 C15 H15 117.7 . . ?
C16 C15 H15 117.7 . . ?
C15 C16 C17 114.3(19) . . ?
C15 C16 H16 122.8 . . ?
C17 C16 H16 122.8 . . ?
C12 C17 C16 122.1(18) . . ?
C12 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C23 123.8(11) . . ?
N2 C22 H22 118.1 . . ?
C23 C22 H22 118.1 . . ?
C22 C23 C24 117.2(10) . . ?
C22 C23 H23 121.4 . . ?
C24 C23 H23 121.4 . . ?
O1 C24 C25 120.6(10) . . ?
O1 C24 C23 119.7(10) . . ?
C25 C24 C23 119.7(10) . . ?
C26 C25 C24 119.4(10) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
N2 C26 C25 121.4(10) . . ?
N2 C26 C27 114.4(9) . . ?
C25 C26 C27 124.2(10) . . ?
N1 C27 C28 121.3(10) . . ?
N1 C27 C26 114.2(9) . . ?
C28 C27 C26 124.5(10) . . ?
C27 C28 C29 120.6(10) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
O2 C29 C28 125.8(11) . . ?
O2 C29 C30 116.4(10) . . ?
C28 C29 C30 117.8(11) . . ?
C31 C30 C29 118.4(11) . . ?
C31 C30 H30 120.8 . . ?
C29 C30 H30 120.8 . . ?
C30 C31 N1 125.1(10) . . ?
C30 C31 H31 117.4 . . ?
N1 C31 H31 117.4 . . ?
O1 C32 C32 153(3) . 3_556 ?
O1 C32 H32A 110.7 . . ?
C32 C32 H32A 92.4 3_556 . ?
O1 C32 H32B 109.9 . . ?
C32 C32 H32B 73.5 3_556 . ?
H32A C32 H32B 109.5 . . ?
O1 C32 H32C 107.9 . . ?
C32 C32 H32C 48.7 3_556 . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O1 C32' H32D 109.5 . . ?
O1 C32' H32E 109.5 . . ?
H32D C32' H32E 109.5 . . ?
O1 C32' H32F 109.5 . . ?
H32D C32' H32F 109.5 . . ?
H32E C32' H32F 109.5 . . ?
O2 C33 H33A 109.5 . . ?
O2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
N1 Ir1 N2 C22 -175.7(10) . . . . ?
C3 Ir1 N2 C22 67.3(19) . . . . ?
C5 Ir1 N2 C22 24.7(10) . . . . ?
C4 Ir1 N2 C22 2.1(12) . . . . ?
C2 Ir1 N2 C22 94.5(10) . . . . ?
C1 Ir1 N2 C22 64.6(10) . . . . ?
Cl1 Ir1 N2 C22 -89.8(9) . . . . ?
Cl2 Ir1 N2 C22 -105.4(9) . . . . ?
Cl3 Ir1 N2 C22 -64.4(9) . . . . ?
N1 Ir1 N2 C26 -0.9(7) . . . . ?
C3 Ir1 N2 C26 -117.9(16) . . . . ?
C5 Ir1 N2 C26 -160.6(8) . . . . ?
C4 Ir1 N2 C26 176.9(8) . . . . ?
C2 Ir1 N2 C26 -90.7(9) . . . . ?
C1 Ir1 N2 C26 -120.6(8) . . . . ?
Cl1 Ir1 N2 C26 84.9(8) . . . . ?
Cl2 Ir1 N2 C26 69.4(8) . . . . ?
Cl3 Ir1 N2 C26 110.3(8) . . . . ?
N2 Ir1 N1 C31 178.1(9) . . . . ?
C3 Ir1 N1 C31 -15.4(10) . . . . ?
C5 Ir1 N1 C31 -82.1(14) . . . . ?
C4 Ir1 N1 C31 0.6(13) . . . . ?
C2 Ir1 N1 C31 -53.2(9) . . . . ?
C1 Ir1 N1 C31 -86.7(9) . . . . ?
Cl1 Ir1 N1 C31 94.0(9) . . . . ?
Cl2 Ir1 N1 C31 95.2(9) . . . . ?
Cl3 Ir1 N1 C31 96.6(9) . . . . ?
N2 Ir1 N1 C27 -1.3(7) . . . . ?
C3 Ir1 N1 C27 165.2(8) . . . . ?
C5 Ir1 N1 C27 98.5(12) . . . . ?
C4 Ir1 N1 C27 -178.8(8) . . . . ?
C2 Ir1 N1 C27 127.4(8) . . . . ?
C1 Ir1 N1 C27 93.9(8) . . . . ?
Cl1 Ir1 N1 C27 -85.4(8) . . . . ?
Cl2 Ir1 N1 C27 -84.2(8) . . . . ?
Cl3 Ir1 N1 C27 -82.8(8) . . . . ?
N1 Ir1 C1 C2 60.9(7) . . . . ?
N2 Ir1 C1 C2 142.1(6) . . . . ?
C3 Ir1 C1 C2 -37.2(6) . . . . ?
C5 Ir1 C1 C2 -116.6(9) . . . . ?
C4 Ir1 C1 C2 -79.0(7) . . . . ?
Cl1 Ir1 C1 C2 -120.6(9) . . . . ?
Cl2 Ir1 C1 C2 -129(2) . . . . ?
Cl3 Ir1 C1 C2 -123.1(7) . . . . ?
N1 Ir1 C1 C5 177.5(6) . . . . ?
N2 Ir1 C1 C5 -101.3(7) . . . . ?
C3 Ir1 C1 C5 79.4(7) . . . . ?
C4 Ir1 C1 C5 37.6(6) . . . . ?
C2 Ir1 C1 C5 116.6(9) . . . . ?
Cl1 Ir1 C1 C5 -4.0(12) . . . . ?
Cl2 Ir1 C1 C5 -13(3) . . . . ?
Cl3 Ir1 C1 C5 -6.5(9) . . . . ?
N1 Ir1 C1 C6 -60.9(11) . . . . ?
N2 Ir1 C1 C6 20.3(11) . . . . ?
C3 Ir1 C1 C6 -158.9(12) . . . . ?
C5 Ir1 C1 C6 121.6(13) . . . . ?
C4 Ir1 C1 C6 159.3(12) . . . . ?
C2 Ir1 C1 C6 -121.7(13) . . . . ?
Cl1 Ir1 C1 C6 117.6(11) . . . . ?
Cl2 Ir1 C1 C6 109(2) . . . . ?
Cl3 Ir1 C1 C6 115.2(10) . . . . ?
C5 C1 C2 C3 -0.3(13) . . . . ?
C6 C1 C2 C3 -177.7(11) . . . . ?
Ir1 C1 C2 C3 61.0(8) . . . . ?
C5 C1 C2 C18 177.5(11) . . . . ?
C6 C1 C2 C18 0.1(19) . . . . ?
Ir1 C1 C2 C18 -121.3(12) . . . . ?
C5 C1 C2 Ir1 -61.3(8) . . . . ?
C6 C1 C2 Ir1 121.4(12) . . . . ?
N1 Ir1 C2 C3 110.9(7) . . . . ?
N2 Ir1 C2 C3 -169.5(6) . . . . ?
C5 Ir1 C2 C3 -79.6(7) . . . . ?
C4 Ir1 C2 C3 -37.5(7) . . . . ?
C1 Ir1 C2 C3 -118.1(9) . . . . ?
Cl1 Ir1 C2 C3 18.4(11) . . . . ?
Cl2 Ir1 C2 C3 48.0(10) . . . . ?
Cl3 Ir1 C2 C3 -22.7(10) . . . . ?
N1 Ir1 C2 C1 -130.9(6) . . . . ?
N2 Ir1 C2 C1 -51.4(8) . . . . ?
C3 Ir1 C2 C1 118.1(9) . . . . ?
C5 Ir1 C2 C1 38.6(6) . . . . ?
C4 Ir1 C2 C1 80.6(7) . . . . ?
Cl1 Ir1 C2 C1 136.6(8) . . . . ?
Cl2 Ir1 C2 C1 166.1(7) . . . . ?
Cl3 Ir1 C2 C1 95.4(8) . . . . ?
N1 Ir1 C2 C18 -11.8(11) . . . . ?
N2 Ir1 C2 C18 67.8(12) . . . . ?
C3 Ir1 C2 C18 -122.7(13) . . . . ?
C5 Ir1 C2 C18 157.7(12) . . . . ?
C4 Ir1 C2 C18 -160.3(12) . . . . ?
C1 Ir1 C2 C18 119.1(13) . . . . ?
Cl1 Ir1 C2 C18 -104.3(12) . . . . ?
Cl2 Ir1 C2 C18 -74.8(13) . . . . ?
Cl3 Ir1 C2 C18 -145.5(9) . . . . ?
C1 C2 C3 C4 1.7(13) . . . . ?
C18 C2 C3 C4 -176.0(12) . . . . ?
Ir1 C2 C3 C4 62.8(8) . . . . ?
C1 C2 C3 C19 173.5(12) . . . . ?
C18 C2 C3 C19 -4(2) . . . . ?
Ir1 C2 C3 C19 -125.4(13) . . . . ?
C1 C2 C3 Ir1 -61.1(8) . . . . ?
C18 C2 C3 Ir1 121.2(12) . . . . ?
N1 Ir1 C3 C4 164.8(7) . . . . ?
N2 Ir1 C3 C4 -82.0(17) . . . . ?
C5 Ir1 C3 C4 -35.5(7) . . . . ?
C2 Ir1 C3 C4 -116.7(10) . . . . ?
C1 Ir1 C3 C4 -79.1(8) . . . . ?
Cl1 Ir1 C3 C4 73.7(8) . . . . ?
Cl2 Ir1 C3 C4 90.1(8) . . . . ?
Cl3 Ir1 C3 C4 48.2(8) . . . . ?
N1 Ir1 C3 C2 -78.4(7) . . . . ?
N2 Ir1 C3 C2 34.7(18) . . . . ?
C5 Ir1 C3 C2 81.2(7) . . . . ?
C4 Ir1 C3 C2 116.7(10) . . . . ?
C1 Ir1 C3 C2 37.7(6) . . . . ?
Cl1 Ir1 C3 C2 -169.5(6) . . . . ?
Cl2 Ir1 C3 C2 -153.2(6) . . . . ?
Cl3 Ir1 C3 C2 165.0(6) . . . . ?
N1 Ir1 C3 C19 42.1(12) . . . . ?
N2 Ir1 C3 C19 155.2(13) . . . . ?
C5 Ir1 C3 C19 -158.2(13) . . . . ?
C4 Ir1 C3 C19 -122.7(15) . . . . ?
C2 Ir1 C3 C19 120.5(14) . . . . ?
C1 Ir1 C3 C19 158.2(13) . . . . ?
Cl1 Ir1 C3 C19 -49.0(12) . . . . ?
Cl2 Ir1 C3 C19 -32.7(13) . . . . ?
Cl3 Ir1 C3 C19 -74.5(12) . . . . ?
C2 C3 C4 C5 -2.5(14) . . . . ?
C19 C3 C4 C5 -174.2(12) . . . . ?
Ir1 C3 C4 C5 60.1(9) . . . . ?
C2 C3 C4 C20 174.5(12) . . . . ?
C19 C3 C4 C20 3(2) . . . . ?
Ir1 C3 C4 C20 -122.9(13) . . . . ?
C2 C3 C4 Ir1 -62.6(8) . . . . ?
C19 C3 C4 Ir1 125.7(13) . . . . ?
N1 Ir1 C4 C3 -25.3(11) . . . . ?
N2 Ir1 C4 C3 158.3(7) . . . . ?
C5 Ir1 C4 C3 121.1(11) . . . . ?
C2 Ir1 C4 C3 38.3(7) . . . . ?
C1 Ir1 C4 C3 81.9(8) . . . . ?
Cl1 Ir1 C4 C3 -114.9(7) . . . . ?
Cl2 Ir1 C4 C3 -106.1(8) . . . . ?
Cl3 Ir1 C4 C3 -131.8(8) . . . . ?
N1 Ir1 C4 C5 -146.4(7) . . . . ?
N2 Ir1 C4 C5 37.3(10) . . . . ?
C3 Ir1 C4 C5 -121.1(11) . . . . ?
C2 Ir1 C4 C5 -82.7(8) . . . . ?
C1 Ir1 C4 C5 -39.1(7) . . . . ?
Cl1 Ir1 C4 C5 124.1(7) . . . . ?
Cl2 Ir1 C4 C5 132.8(7) . . . . ?
Cl3 Ir1 C4 C5 107.2(8) . . . . ?
N1 Ir1 C4 C20 93.8(12) . . . . ?
N2 Ir1 C4 C20 -82.5(13) . . . . ?
C3 Ir1 C4 C20 119.2(15) . . . . ?
C5 Ir1 C4 C20 -119.8(14) . . . . ?
C2 Ir1 C4 C20 157.5(13) . . . . ?
C1 Ir1 C4 C20 -158.9(13) . . . . ?
Cl1 Ir1 C4 C20 4.3(12) . . . . ?
Cl2 Ir1 C4 C20 13.0(12) . . . . ?
Cl3 Ir1 C4 C20 -12.6(11) . . . . ?
C3 C4 C5 C1 2.3(14) . . . . ?
C20 C4 C5 C1 -174.7(12) . . . . ?
Ir1 C4 C5 C1 62.3(8) . . . . ?
C3 C4 C5 C21 175.0(12) . . . . ?
C20 C4 C5 C21 -2(2) . . . . ?
Ir1 C4 C5 C21 -124.9(13) . . . . ?
C3 C4 C5 Ir1 -60.1(9) . . . . ?
C20 C4 C5 Ir1 123.0(13) . . . . ?
C2 C1 C5 C4 -1.2(13) . . . . ?
C6 C1 C5 C4 176.2(11) . . . . ?
Ir1 C1 C5 C4 -62.7(8) . . . . ?
C2 C1 C5 C21 -174.0(11) . . . . ?
C6 C1 C5 C21 3(2) . . . . ?
Ir1 C1 C5 C21 124.5(12) . . . . ?
C2 C1 C5 Ir1 61.5(8) . . . . ?
C6 C1 C5 Ir1 -121.1(12) . . . . ?
N1 Ir1 C5 C4 110.0(11) . . . . ?
N2 Ir1 C5 C4 -155.3(7) . . . . ?
C3 Ir1 C5 C4 35.4(7) . . . . ?
C2 Ir1 C5 C4 78.0(7) . . . . ?
C1 Ir1 C5 C4 116.3(10) . . . . ?
Cl1 Ir1 C5 C4 -65.7(8) . . . . ?
Cl2 Ir1 C5 C4 -66.6(9) . . . . ?
Cl3 Ir1 C5 C4 -68.8(7) . . . . ?
N1 Ir1 C5 C1 -6.3(14) . . . . ?
N2 Ir1 C5 C1 88.4(7) . . . . ?
C3 Ir1 C5 C1 -80.9(7) . . . . ?
C4 Ir1 C5 C1 -116.3(10) . . . . ?
C2 Ir1 C5 C1 -38.3(6) . . . . ?
Cl1 Ir1 C5 C1 178.1(6) . . . . ?
Cl2 Ir1 C5 C1 177.1(6) . . . . ?
Cl3 Ir1 C5 C1 175.0(7) . . . . ?
N1 Ir1 C5 C21 -127.7(12) . . . . ?
N2 Ir1 C5 C21 -33.0(12) . . . . ?
C3 Ir1 C5 C21 157.7(13) . . . . ?
C4 Ir1 C5 C21 122.3(15) . . . . ?
C2 Ir1 C5 C21 -159.7(13) . . . . ?
C1 Ir1 C5 C21 -121.4(14) . . . . ?
Cl1 Ir1 C5 C21 56.7(12) . . . . ?
Cl2 Ir1 C5 C21 55.7(13) . . . . ?
Cl3 Ir1 C5 C21 53.6(11) . . . . ?
C2 C1 C6 C11 -51.2(18) . . . . ?
C5 C1 C6 C11 132.0(13) . . . . ?
Ir1 C1 C6 C11 40.7(16) . . . . ?
C2 C1 C6 C7 125.6(14) . . . . ?
C5 C1 C6 C7 -51.2(17) . . . . ?
Ir1 C1 C6 C7 -142.5(10) . . . . ?
C11 C6 C7 C8 0.7(19) . . . . ?
C1 C6 C7 C8 -176.3(12) . . . . ?
C6 C7 C8 C9 2(2) . . . . ?
C7 C8 C9 C10 -4(2) . . . . ?
C7 C8 C9 C12 176.8(13) . . . . ?
C8 C9 C10 C11 2(2) . . . . ?
C12 C9 C10 C11 -178.2(13) . . . . ?
C9 C10 C11 C6 1(2) . . . . ?
C7 C6 C11 C10 -2.1(18) . . . . ?
C1 C6 C11 C10 174.7(12) . . . . ?
C8 C9 C12 C17 171.4(16) . . . . ?
C10 C9 C12 C17 -8(2) . . . . ?
C8 C9 C12 C13 -12(2) . . . . ?
C10 C9 C12 C13 168.3(15) . . . . ?
C17 C12 C13 C14 -1(3) . . . . ?
C9 C12 C13 C14 -177.1(16) . . . . ?
C12 C13 C14 C15 -3(3) . . . . ?
C13 C14 C15 C16 5(3) . . . . ?
C14 C15 C16 C17 -4(3) . . . . ?
C13 C12 C17 C16 2(3) . . . . ?
C9 C12 C17 C16 178.7(15) . . . . ?
C15 C16 C17 C12 0(3) . . . . ?
C26 N2 C22 C23 1.0(17) . . . . ?
Ir1 N2 C22 C23 175.7(9) . . . . ?
N2 C22 C23 C24 -1.3(19) . . . . ?
C32 O1 C24 C25 17(2) . . . . ?
C32' O1 C24 C25 -160.6(16) . . . . ?
C32 O1 C24 C23 -161.1(17) . . . . ?
C32' O1 C24 C23 21(2) . . . . ?
C22 C23 C24 O1 -180.0(11) . . . . ?
C22 C23 C24 C25 2.0(18) . . . . ?
O1 C24 C25 C26 179.6(11) . . . . ?
C23 C24 C25 C26 -2.3(17) . . . . ?
C22 N2 C26 C25 -1.3(16) . . . . ?
Ir1 N2 C26 C25 -176.4(8) . . . . ?
C22 N2 C26 C27 177.9(9) . . . . ?
Ir1 N2 C26 C27 2.8(12) . . . . ?
C24 C25 C26 N2 2.0(17) . . . . ?
C24 C25 C26 C27 -177.1(10) . . . . ?
C31 N1 C27 C28 2.3(15) . . . . ?
Ir1 N1 C27 C28 -178.3(8) . . . . ?
C31 N1 C27 C26 -176.3(9) . . . . ?
Ir1 N1 C27 C26 3.2(12) . . . . ?
N2 C26 C27 N1 -3.9(14) . . . . ?
C25 C26 C27 N1 175.3(10) . . . . ?
N2 C26 C27 C28 177.6(10) . . . . ?
C25 C26 C27 C28 -3.2(17) . . . . ?
N1 C27 C28 C29 1.3(16) . . . . ?
C26 C27 C28 C29 179.7(10) . . . . ?
C33 O2 C29 C28 -4.2(18) . . . . ?
C33 O2 C29 C30 175.8(11) . . . . ?
C27 C28 C29 O2 177.0(11) . . . . ?
C27 C28 C29 C30 -3.0(17) . . . . ?
O2 C29 C30 C31 -178.9(10) . . . . ?
C28 C29 C30 C31 1.1(17) . . . . ?
C29 C30 C31 N1 2.8(19) . . . . ?
C27 N1 C31 C30 -4.4(17) . . . . ?
Ir1 N1 C31 C30 176.2(9) . . . . ?
C24 O1 C32 C32 -144(5) . . . 3_556 ?
C32' O1 C32 C32 34(6) . . . 3_556 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.579
_refine_diff_density_min         -1.029
_refine_diff_density_rms         0.160
####################################################################### 
# 
# 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_180304d
_database_code_depnum_ccdc_archive 'CCDC 1569685'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31.50 H29 Cl3 F6 Ir N2 O0.50 P'
_chemical_formula_weight         887.09

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'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9410(8)
_cell_length_b                   11.1991(9)
_cell_length_c                   14.9659(11)
_cell_angle_alpha                93.0900(10)
_cell_angle_beta                 109.773(2)
_cell_angle_gamma                90.7840(10)
_cell_volume                     1722.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4848
_cell_measurement_theta_min      2.734
_cell_measurement_theta_max      27.537

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             866
_exptl_absorpt_coefficient_mu    4.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2420
_exptl_absorpt_correction_T_max  0.5175
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8782
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5992
_reflns_number_gt                5096
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0727P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5992
_refine_ls_number_parameters     457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.52719(2) 0.21384(2) 0.301586(16) 0.04091(12) Uani 1 1 d . . .
Cl1 Cl 0.92070(19) -0.1218(2) 0.61451(15) 0.0715(6) Uani 1 1 d . . .
Cl2 Cl 0.2164(2) -0.29242(19) 0.30077(18) 0.0729(6) Uani 1 1 d . . .
Cl3 Cl 0.4708(2) 0.29458(17) 0.43268(13) 0.0591(5) Uani 1 1 d . . .
O1 O 0.080(2) 0.556(2) 0.4491(16) 0.171(8) Uani 0.50 1 d P . .
H1A H 0.0243 0.5653 0.3974 0.205 Uiso 0.25 1 calc PR A 1
H1B H 0.0309 0.5312 0.4783 0.205 Uiso 0.25 1 d PR A 2
F1 F 0.2691(8) 0.3317(6) 0.8134(5) 0.137(3) Uani 1 1 d . B .
F2 F 0.1773(7) 0.0909(5) 0.6884(4) 0.110(2) Uani 1 1 d . B .
F3 F 0.121(2) 0.2703(14) 0.6658(14) 0.128(11) Uani 0.57(4) 1 d P B 1
F4 F 0.328(2) 0.2445(17) 0.7106(16) 0.117(9) Uani 0.57(4) 1 d P B 1
F5 F 0.107(2) 0.1760(18) 0.7875(16) 0.136(9) Uani 0.57(4) 1 d P B 1
F6 F 0.315(2) 0.1522(13) 0.8375(13) 0.131(13) Uani 0.57(4) 1 d P B 1
F3' F 0.240(4) 0.2680(17) 0.6620(15) 0.116(11) Uani 0.43(4) 1 d P B 2
F4' F 0.096(2) 0.276(2) 0.733(3) 0.130(12) Uani 0.43(4) 1 d P B 2
F5' F 0.211(3) 0.1578(16) 0.8391(14) 0.112(12) Uani 0.43(4) 1 d P B 2
F6' F 0.3546(16) 0.1511(19) 0.768(2) 0.109(10) Uani 0.43(4) 1 d P B 2
N1 N 0.6609(5) 0.1113(5) 0.4024(4) 0.0426(12) Uani 1 1 d . . .
N2 N 0.4187(5) 0.0594(5) 0.3046(4) 0.0427(12) Uani 1 1 d . . .
P1 P 0.2204(2) 0.21118(18) 0.75151(14) 0.0563(5) Uani 1 1 d . . .
C1 C 0.7797(6) 0.1515(7) 0.4581(5) 0.0523(18) Uani 1 1 d . . .
H1 H 0.8067 0.2287 0.4517 0.063 Uiso 1 1 calc R . .
C2 C 0.8634(7) 0.0834(7) 0.5244(5) 0.0532(18) Uani 1 1 d . . .
H2 H 0.9458 0.1128 0.5617 0.064 Uiso 1 1 calc R . .
C3 C 0.8205(6) -0.0305(7) 0.5335(5) 0.0480(16) Uani 1 1 d . . .
C4 C 0.6968(6) -0.0730(6) 0.4792(5) 0.0435(15) Uani 1 1 d . . .
H4 H 0.6674 -0.1493 0.4857 0.052 Uiso 1 1 calc R . .
C5 C 0.6181(6) 0.0021(6) 0.4148(4) 0.0407(14) Uani 1 1 d . . .
C6 C 0.4836(6) -0.0310(5) 0.3563(4) 0.0362(13) Uani 1 1 d . . .
C7 C 0.4249(7) -0.1401(6) 0.3556(4) 0.0449(15) Uani 1 1 d . . .
H7 H 0.4720 -0.2015 0.3894 0.054 Uiso 1 1 calc R . .
C8 C 0.2937(7) -0.1568(6) 0.3034(5) 0.0479(16) Uani 1 1 d . . .
C9 C 0.2255(7) -0.0648(7) 0.2531(5) 0.0507(17) Uani 1 1 d . . .
H9 H 0.1370 -0.0737 0.2190 0.061 Uiso 1 1 calc R . .
C10 C 0.2932(7) 0.0404(7) 0.2550(5) 0.0500(17) Uani 1 1 d . . .
H10 H 0.2485 0.1018 0.2197 0.060 Uiso 1 1 calc R . .
C11 C 0.4191(7) 0.3038(6) 0.1754(5) 0.0440(15) Uani 1 1 d . . .
C12 C 0.4903(6) 0.2059(6) 0.1505(5) 0.0442(15) Uani 1 1 d . . .
C13 C 0.6259(7) 0.2297(6) 0.1983(5) 0.0478(16) Uani 1 1 d . . .
C14 C 0.6414(6) 0.3395(6) 0.2540(5) 0.0458(16) Uani 1 1 d . . .
C15 C 0.5145(7) 0.3891(6) 0.2397(5) 0.0475(16) Uani 1 1 d . . .
C16 C 0.2763(6) 0.3188(6) 0.1383(5) 0.0422(15) Uani 1 1 d . . .
C17 C 0.2109(7) 0.3081(6) 0.0407(5) 0.0488(16) Uani 1 1 d . . .
H17 H 0.2568 0.2933 -0.0006 0.059 Uiso 1 1 calc R . .
C18 C 0.0798(7) 0.3193(7) 0.0056(5) 0.0521(17) Uani 1 1 d . . .
H18 H 0.0376 0.3114 -0.0599 0.063 Uiso 1 1 calc R . .
C19 C 0.0071(6) 0.3423(6) 0.0643(4) 0.0455(15) Uani 1 1 d . . .
C20 C 0.0739(7) 0.3564(6) 0.1611(5) 0.0505(17) Uani 1 1 d . . .
H20 H 0.0287 0.3746 0.2024 0.061 Uiso 1 1 calc R . .
C21 C 0.2068(7) 0.3437(7) 0.1973(5) 0.0515(17) Uani 1 1 d . . .
H21 H 0.2496 0.3522 0.2627 0.062 Uiso 1 1 calc R . .
C22 C -0.1386(7) 0.3464(6) 0.0277(5) 0.0474(16) Uani 1 1 d . . .
C23 C -0.2108(8) 0.2705(8) -0.0478(6) 0.068(2) Uani 1 1 d . . .
H23 H -0.1683 0.2207 -0.0787 0.081 Uiso 1 1 calc R . .
C24 C -0.3450(8) 0.2666(8) -0.0786(6) 0.070(2) Uani 1 1 d . . .
H24 H -0.3922 0.2132 -0.1285 0.084 Uiso 1 1 calc R . .
C25 C -0.4073(8) 0.3415(8) -0.0355(6) 0.065(2) Uani 1 1 d . . .
H25 H -0.4976 0.3389 -0.0553 0.079 Uiso 1 1 calc R . .
C26 C -0.3370(8) 0.4213(7) 0.0377(6) 0.063(2) Uani 1 1 d . . .
H26 H -0.3806 0.4734 0.0660 0.075 Uiso 1 1 calc R . .
C27 C -0.2026(7) 0.4253(6) 0.0698(5) 0.0511(17) Uani 1 1 d . . .
H27 H -0.1559 0.4800 0.1189 0.061 Uiso 1 1 calc R . .
C28 C 0.4319(8) 0.1005(6) 0.0823(5) 0.0558(18) Uani 1 1 d . . .
H28A H 0.4330 0.1168 0.0203 0.084 Uiso 1 1 calc R . .
H28B H 0.3438 0.0861 0.0793 0.084 Uiso 1 1 calc R . .
H28C H 0.4815 0.0311 0.1037 0.084 Uiso 1 1 calc R . .
C29 C 0.7330(7) 0.1552(7) 0.1888(6) 0.061(2) Uani 1 1 d . . .
H29A H 0.7004 0.0748 0.1679 0.091 Uiso 1 1 calc R . .
H29B H 0.8014 0.1551 0.2493 0.091 Uiso 1 1 calc R . .
H29C H 0.7661 0.1877 0.1432 0.091 Uiso 1 1 calc R . .
C30 C 0.7659(8) 0.4040(8) 0.3082(6) 0.069(2) Uani 1 1 d . . .
H30A H 0.8346 0.3481 0.3248 0.104 Uiso 1 1 calc R . .
H30B H 0.7594 0.4428 0.3651 0.104 Uiso 1 1 calc R . .
H30C H 0.7844 0.4628 0.2698 0.104 Uiso 1 1 calc R . .
C31 C 0.4873(9) 0.5048(6) 0.2795(6) 0.064(2) Uani 1 1 d . . .
H31A H 0.4034 0.5300 0.2410 0.096 Uiso 1 1 calc R . .
H31B H 0.5525 0.5635 0.2802 0.096 Uiso 1 1 calc R . .
H31C H 0.4884 0.4963 0.3433 0.096 Uiso 1 1 calc R . .
C32 C 0.158(3) 0.459(2) 0.4403(16) 0.116(9) Uani 0.50 1 d P . .
H32A H 0.2474 0.4798 0.4739 0.174 Uiso 0.50 1 calc PR . .
H32B H 0.1450 0.4406 0.3743 0.174 Uiso 0.50 1 calc PR . .
H32C H 0.1328 0.3899 0.4666 0.174 Uiso 0.50 1 calc PR . .


_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 N2 2.095(5) . ?
Ir1 N1 2.115(5) . ?
Ir1 C12 2.155(6) . ?
Ir1 C11 2.169(6) . ?
Ir1 C14 2.170(6) . ?
Ir1 C13 2.178(7) . ?
Ir1 C15 2.201(7) . ?
Ir1 Cl3 2.3856(18) . ?
Cl1 C3 1.726(7) . ?
Cl2 C8 1.720(7) . ?
O1 C32 1.42(3) . ?
O1 H1A 0.8200 . ?
O1 H1B 0.8500 . ?
F1 P1 1.573(6) . ?
F2 P1 1.572(5) . ?
F3 P1 1.559(12) . ?
F4 P1 1.550(12) . ?
F5 P1 1.564(13) . ?
F6 P1 1.539(12) . ?
F3' P1 1.589(18) . ?
F4' P1 1.498(19) . ?
F5' P1 1.503(16) . ?
F6' P1 1.571(15) . ?
N1 C1 1.341(8) . ?
N1 C5 1.348(8) . ?
N2 C10 1.330(8) . ?
N2 C6 1.363(8) . ?
C1 C2 1.375(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(9) . ?
C4 C5 1.387(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.466(9) . ?
C6 C7 1.370(9) . ?
C7 C8 1.388(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(10) . ?
C9 C10 1.377(10) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.457(9) . ?
C11 C15 1.458(10) . ?
C11 C16 1.486(10) . ?
C12 C13 1.427(9) . ?
C12 C28 1.501(9) . ?
C13 C14 1.422(10) . ?
C13 C29 1.488(10) . ?
C14 C15 1.454(10) . ?
C14 C30 1.483(10) . ?
C15 C31 1.473(10) . ?
C16 C21 1.367(9) . ?
C16 C17 1.390(9) . ?
C17 C18 1.361(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(9) . ?
C19 C22 1.502(9) . ?
C20 C21 1.382(10) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.378(10) . ?
C22 C27 1.388(10) . ?
C23 C24 1.381(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.356(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(10) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

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
N2 Ir1 N1 76.1(2) . . ?
N2 Ir1 C12 97.6(2) . . ?
N1 Ir1 C12 126.5(2) . . ?
N2 Ir1 C11 107.3(2) . . ?
N1 Ir1 C11 165.1(2) . . ?
C12 Ir1 C11 39.4(2) . . ?
N2 Ir1 C14 159.9(2) . . ?
N1 Ir1 C14 106.6(2) . . ?
C12 Ir1 C14 64.5(3) . . ?
C11 Ir1 C14 65.1(2) . . ?
N2 Ir1 C13 121.9(2) . . ?
N1 Ir1 C13 100.5(2) . . ?
C12 Ir1 C13 38.5(2) . . ?
C11 Ir1 C13 65.2(2) . . ?
C14 Ir1 C13 38.2(3) . . ?
N2 Ir1 C15 143.4(2) . . ?
N1 Ir1 C15 140.3(2) . . ?
C12 Ir1 C15 65.2(3) . . ?
C11 Ir1 C15 39.0(3) . . ?
C14 Ir1 C15 38.9(3) . . ?
C13 Ir1 C15 64.8(3) . . ?
N2 Ir1 Cl3 87.30(16) . . ?
N1 Ir1 Cl3 85.65(15) . . ?
C12 Ir1 Cl3 147.74(18) . . ?
C11 Ir1 Cl3 108.76(19) . . ?
C14 Ir1 Cl3 112.6(2) . . ?
C13 Ir1 Cl3 150.8(2) . . ?
C15 Ir1 Cl3 92.19(18) . . ?
C32 O1 H1A 109.5 . . ?
C32 O1 H1B 106.5 . . ?
H1A O1 H1B 99.0 . . ?
C1 N1 C5 119.0(6) . . ?
C1 N1 Ir1 124.2(5) . . ?
C5 N1 Ir1 116.6(4) . . ?
C10 N2 C6 117.8(6) . . ?
C10 N2 Ir1 124.6(5) . . ?
C6 N2 Ir1 117.5(4) . . ?
F4' P1 F5' 93.3(15) . . ?
F4' P1 F6 135.0(15) . . ?
F5' P1 F6 44.3(10) . . ?
F4' P1 F4 124.3(13) . . ?
F5' P1 F4 137.8(15) . . ?
F6 P1 F4 93.8(12) . . ?
F4' P1 F3 43.3(10) . . ?
F5' P1 F3 133.8(15) . . ?
F6 P1 F3 178.1(14) . . ?
F4 P1 F3 88.1(11) . . ?
F4' P1 F5 54.5(11) . . ?
F5' P1 F5 44.7(10) . . ?
F6 P1 F5 88.5(11) . . ?
F4 P1 F5 177.1(10) . . ?
F3 P1 F5 89.6(11) . . ?
F4' P1 F6' 175.8(14) . . ?
F5' P1 F6' 90.1(13) . . ?
F6 P1 F6' 47.6(9) . . ?
F4 P1 F6' 51.7(9) . . ?
F3 P1 F6' 134.2(13) . . ?
F5 P1 F6' 129.6(12) . . ?
F4' P1 F2 103.8(11) . . ?
F5' P1 F2 93.6(8) . . ?
F6 P1 F2 94.8(7) . . ?
F4 P1 F2 94.8(6) . . ?
F3 P1 F2 85.2(7) . . ?
F5 P1 F2 83.2(7) . . ?
F6' P1 F2 78.4(8) . . ?
F4' P1 F1 78.1(10) . . ?
F5' P1 F1 87.8(8) . . ?
F6 P1 F1 84.8(6) . . ?
F4 P1 F1 82.8(6) . . ?
F3 P1 F1 95.3(7) . . ?
F5 P1 F1 99.3(7) . . ?
F6' P1 F1 99.5(8) . . ?
F2 P1 F1 177.5(5) . . ?
F4' P1 F3' 89.6(13) . . ?
F5' P1 F3' 176.5(17) . . ?
F6 P1 F3' 132.4(15) . . ?
F4 P1 F3' 38.7(9) . . ?
F3 P1 F3' 49.5(10) . . ?
F5 P1 F3' 138.8(14) . . ?
F6' P1 F3' 87.0(13) . . ?
F2 P1 F3' 87.6(8) . . ?
F1 P1 F3' 90.9(8) . . ?
N1 C1 C2 122.8(7) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 117.6(6) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C2 C3 C4 121.0(6) . . ?
C2 C3 Cl1 120.2(5) . . ?
C4 C3 Cl1 118.8(6) . . ?
C3 C4 C5 117.7(6) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
N1 C5 C4 121.8(6) . . ?
N1 C5 C6 115.5(5) . . ?
C4 C5 C6 122.7(6) . . ?
N2 C6 C7 122.3(6) . . ?
N2 C6 C5 113.6(5) . . ?
C7 C6 C5 124.1(6) . . ?
C6 C7 C8 118.5(6) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C9 C8 C7 119.9(6) . . ?
C9 C8 Cl2 120.1(5) . . ?
C7 C8 Cl2 119.9(6) . . ?
C10 C9 C8 117.7(6) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
N2 C10 C9 123.8(7) . . ?
N2 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C12 C11 C15 107.3(6) . . ?
C12 C11 C16 126.9(6) . . ?
C15 C11 C16 125.7(6) . . ?
C12 C11 Ir1 69.8(4) . . ?
C15 C11 Ir1 71.7(4) . . ?
C16 C11 Ir1 126.5(4) . . ?
C13 C12 C11 108.6(6) . . ?
C13 C12 C28 125.4(6) . . ?
C11 C12 C28 126.0(6) . . ?
C13 C12 Ir1 71.6(4) . . ?
C11 C12 Ir1 70.8(3) . . ?
C28 C12 Ir1 125.6(5) . . ?
C14 C13 C12 108.1(6) . . ?
C14 C13 C29 125.9(7) . . ?
C12 C13 C29 126.0(7) . . ?
C14 C13 Ir1 70.6(4) . . ?
C12 C13 Ir1 69.9(4) . . ?
C29 C13 Ir1 126.8(5) . . ?
C13 C14 C15 109.4(6) . . ?
C13 C14 C30 126.4(7) . . ?
C15 C14 C30 123.7(7) . . ?
C13 C14 Ir1 71.2(4) . . ?
C15 C14 Ir1 71.7(4) . . ?
C30 C14 Ir1 129.7(5) . . ?
C14 C15 C11 106.6(6) . . ?
C14 C15 C31 127.0(7) . . ?
C11 C15 C31 126.5(7) . . ?
C14 C15 Ir1 69.4(4) . . ?
C11 C15 Ir1 69.3(4) . . ?
C31 C15 Ir1 127.6(5) . . ?
C21 C16 C17 118.7(6) . . ?
C21 C16 C11 122.0(6) . . ?
C17 C16 C11 119.3(6) . . ?
C18 C17 C16 120.1(6) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 122.2(6) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C20 C19 C18 117.1(6) . . ?
C20 C19 C22 119.7(6) . . ?
C18 C19 C22 123.1(6) . . ?
C21 C20 C19 121.0(6) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C16 C21 C20 120.9(6) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C27 118.9(7) . . ?
C23 C22 C19 120.3(6) . . ?
C27 C22 C19 120.8(6) . . ?
C22 C23 C24 121.4(8) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 119.4(8) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.1(8) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 121.1(7) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C26 C27 C22 119.0(7) . . ?
C26 C27 H27 120.5 . . ?
C22 C27 H27 120.5 . . ?
C12 C28 H28A 109.5 . . ?
C12 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C12 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C13 C29 H29A 109.5 . . ?
C13 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C13 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C14 C30 H30A 109.5 . . ?
C14 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C14 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C15 C31 H31A 109.5 . . ?
C15 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C15 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O1 C32 H32A 109.5 . . ?
O1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
N2 Ir1 N1 C1 -171.4(6) . . . . ?
C12 Ir1 N1 C1 99.4(6) . . . . ?
C11 Ir1 N1 C1 83.1(10) . . . . ?
C14 Ir1 N1 C1 29.2(6) . . . . ?
C13 Ir1 N1 C1 68.0(6) . . . . ?
C15 Ir1 N1 C1 5.1(7) . . . . ?
Cl3 Ir1 N1 C1 -83.1(6) . . . . ?
N2 Ir1 N1 C5 3.7(4) . . . . ?
C12 Ir1 N1 C5 -85.6(5) . . . . ?
C11 Ir1 N1 C5 -101.8(9) . . . . ?
C14 Ir1 N1 C5 -155.7(5) . . . . ?
C13 Ir1 N1 C5 -116.9(5) . . . . ?
C15 Ir1 N1 C5 -179.9(4) . . . . ?
Cl3 Ir1 N1 C5 91.9(4) . . . . ?
N1 Ir1 N2 C10 177.4(6) . . . . ?
C12 Ir1 N2 C10 -56.8(6) . . . . ?
C11 Ir1 N2 C10 -17.6(6) . . . . ?
C14 Ir1 N2 C10 -82.0(8) . . . . ?
C13 Ir1 N2 C10 -88.8(6) . . . . ?
C15 Ir1 N2 C10 1.2(8) . . . . ?
Cl3 Ir1 N2 C10 91.2(5) . . . . ?
N1 Ir1 N2 C6 -7.1(4) . . . . ?
C12 Ir1 N2 C6 118.8(5) . . . . ?
C11 Ir1 N2 C6 157.9(4) . . . . ?
C14 Ir1 N2 C6 93.5(7) . . . . ?
C13 Ir1 N2 C6 86.8(5) . . . . ?
C15 Ir1 N2 C6 176.7(4) . . . . ?
Cl3 Ir1 N2 C6 -93.3(4) . . . . ?
C5 N1 C1 C2 3.7(11) . . . . ?
Ir1 N1 C1 C2 178.6(5) . . . . ?
N1 C1 C2 C3 -0.9(11) . . . . ?
C1 C2 C3 C4 -1.3(11) . . . . ?
C1 C2 C3 Cl1 179.4(6) . . . . ?
C2 C3 C4 C5 0.7(10) . . . . ?
Cl1 C3 C4 C5 179.9(5) . . . . ?
C1 N1 C5 C4 -4.4(10) . . . . ?
Ir1 N1 C5 C4 -179.7(5) . . . . ?
C1 N1 C5 C6 175.3(6) . . . . ?
Ir1 N1 C5 C6 -0.1(7) . . . . ?
C3 C4 C5 N1 2.2(10) . . . . ?
C3 C4 C5 C6 -177.4(6) . . . . ?
C10 N2 C6 C7 2.4(9) . . . . ?
Ir1 N2 C6 C7 -173.4(5) . . . . ?
C10 N2 C6 C5 -175.0(6) . . . . ?
Ir1 N2 C6 C5 9.1(7) . . . . ?
N1 C5 C6 N2 -5.8(8) . . . . ?
C4 C5 C6 N2 173.8(6) . . . . ?
N1 C5 C6 C7 176.8(6) . . . . ?
C4 C5 C6 C7 -3.6(10) . . . . ?
N2 C6 C7 C8 -2.7(9) . . . . ?
C5 C6 C7 C8 174.5(6) . . . . ?
C6 C7 C8 C9 0.5(10) . . . . ?
C6 C7 C8 Cl2 -179.9(5) . . . . ?
C7 C8 C9 C10 1.7(10) . . . . ?
Cl2 C8 C9 C10 -177.8(5) . . . . ?
C6 N2 C10 C9 0.0(10) . . . . ?
Ir1 N2 C10 C9 175.5(5) . . . . ?
C8 C9 C10 N2 -2.0(11) . . . . ?
N2 Ir1 C11 C12 -80.6(4) . . . . ?
N1 Ir1 C11 C12 20.8(10) . . . . ?
C14 Ir1 C11 C12 79.4(4) . . . . ?
C13 Ir1 C11 C12 37.2(4) . . . . ?
C15 Ir1 C11 C12 117.1(6) . . . . ?
Cl3 Ir1 C11 C12 -173.7(3) . . . . ?
N2 Ir1 C11 C15 162.2(4) . . . . ?
N1 Ir1 C11 C15 -96.3(9) . . . . ?
C12 Ir1 C11 C15 -117.1(6) . . . . ?
C14 Ir1 C11 C15 -37.7(4) . . . . ?
C13 Ir1 C11 C15 -80.0(4) . . . . ?
Cl3 Ir1 C11 C15 69.2(4) . . . . ?
N2 Ir1 C11 C16 41.0(6) . . . . ?
N1 Ir1 C11 C16 142.4(7) . . . . ?
C12 Ir1 C11 C16 121.6(7) . . . . ?
C14 Ir1 C11 C16 -159.0(7) . . . . ?
C13 Ir1 C11 C16 158.7(7) . . . . ?
C15 Ir1 C11 C16 -121.3(7) . . . . ?
Cl3 Ir1 C11 C16 -52.1(6) . . . . ?
C15 C11 C12 C13 0.3(7) . . . . ?
C16 C11 C12 C13 176.9(6) . . . . ?
Ir1 C11 C12 C13 -62.0(4) . . . . ?
C15 C11 C12 C28 -177.0(6) . . . . ?
C16 C11 C12 C28 -0.4(10) . . . . ?
Ir1 C11 C12 C28 120.7(7) . . . . ?
C15 C11 C12 Ir1 62.3(4) . . . . ?
C16 C11 C12 Ir1 -121.1(6) . . . . ?
N2 Ir1 C12 C13 -133.7(4) . . . . ?
N1 Ir1 C12 C13 -55.4(5) . . . . ?
C11 Ir1 C12 C13 118.1(6) . . . . ?
C14 Ir1 C12 C13 37.0(4) . . . . ?
C15 Ir1 C12 C13 80.1(4) . . . . ?
Cl3 Ir1 C12 C13 129.3(4) . . . . ?
N2 Ir1 C12 C11 108.2(4) . . . . ?
N1 Ir1 C12 C11 -173.5(3) . . . . ?
C14 Ir1 C12 C11 -81.2(4) . . . . ?
C13 Ir1 C12 C11 -118.1(6) . . . . ?
C15 Ir1 C12 C11 -38.0(4) . . . . ?
Cl3 Ir1 C12 C11 11.2(6) . . . . ?
N2 Ir1 C12 C28 -12.9(6) . . . . ?
N1 Ir1 C12 C28 65.5(6) . . . . ?
C11 Ir1 C12 C28 -121.1(7) . . . . ?
C14 Ir1 C12 C28 157.8(6) . . . . ?
C13 Ir1 C12 C28 120.8(7) . . . . ?
C15 Ir1 C12 C28 -159.1(7) . . . . ?
Cl3 Ir1 C12 C28 -109.8(6) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C28 C12 C13 C14 178.3(6) . . . . ?
Ir1 C12 C13 C14 -60.6(4) . . . . ?
C11 C12 C13 C29 -177.0(6) . . . . ?
C28 C12 C13 C29 0.4(11) . . . . ?
Ir1 C12 C13 C29 121.5(7) . . . . ?
C11 C12 C13 Ir1 61.5(4) . . . . ?
C28 C12 C13 Ir1 -121.2(7) . . . . ?
N2 Ir1 C13 C14 176.3(3) . . . . ?
N1 Ir1 C13 C14 -103.6(4) . . . . ?
C12 Ir1 C13 C14 118.6(6) . . . . ?
C11 Ir1 C13 C14 80.6(4) . . . . ?
C15 Ir1 C13 C14 37.4(4) . . . . ?
Cl3 Ir1 C13 C14 -3.7(6) . . . . ?
N2 Ir1 C13 C12 57.6(4) . . . . ?
N1 Ir1 C13 C12 137.7(4) . . . . ?
C11 Ir1 C13 C12 -38.0(4) . . . . ?
C14 Ir1 C13 C12 -118.6(6) . . . . ?
C15 Ir1 C13 C12 -81.2(4) . . . . ?
Cl3 Ir1 C13 C12 -122.3(4) . . . . ?
N2 Ir1 C13 C29 -62.9(7) . . . . ?
N1 Ir1 C13 C29 17.2(7) . . . . ?
C12 Ir1 C13 C29 -120.6(8) . . . . ?
C11 Ir1 C13 C29 -158.6(8) . . . . ?
C14 Ir1 C13 C29 120.8(8) . . . . ?
C15 Ir1 C13 C29 158.2(7) . . . . ?
Cl3 Ir1 C13 C29 117.1(6) . . . . ?
C12 C13 C14 C15 -1.8(7) . . . . ?
C29 C13 C14 C15 176.1(6) . . . . ?
Ir1 C13 C14 C15 -61.9(4) . . . . ?
C12 C13 C14 C30 -173.9(7) . . . . ?
C29 C13 C14 C30 4.0(11) . . . . ?
Ir1 C13 C14 C30 126.0(7) . . . . ?
C12 C13 C14 Ir1 60.1(4) . . . . ?
C29 C13 C14 Ir1 -121.9(7) . . . . ?
N2 Ir1 C14 C13 -9.3(8) . . . . ?
N1 Ir1 C14 C13 85.8(4) . . . . ?
C12 Ir1 C14 C13 -37.2(4) . . . . ?
C11 Ir1 C14 C13 -80.9(4) . . . . ?
C15 Ir1 C14 C13 -118.8(6) . . . . ?
Cl3 Ir1 C14 C13 178.1(3) . . . . ?
N2 Ir1 C14 C15 109.5(7) . . . . ?
N1 Ir1 C14 C15 -155.4(4) . . . . ?
C12 Ir1 C14 C15 81.5(4) . . . . ?
C11 Ir1 C14 C15 37.8(4) . . . . ?
C13 Ir1 C14 C15 118.8(6) . . . . ?
Cl3 Ir1 C14 C15 -63.2(4) . . . . ?
N2 Ir1 C14 C30 -131.5(7) . . . . ?
N1 Ir1 C14 C30 -36.4(7) . . . . ?
C12 Ir1 C14 C30 -159.4(8) . . . . ?
C11 Ir1 C14 C30 156.9(8) . . . . ?
C13 Ir1 C14 C30 -122.2(9) . . . . ?
C15 Ir1 C14 C30 119.1(9) . . . . ?
Cl3 Ir1 C14 C30 55.9(7) . . . . ?
C13 C14 C15 C11 1.9(7) . . . . ?
C30 C14 C15 C11 174.3(6) . . . . ?
Ir1 C14 C15 C11 -59.7(4) . . . . ?
C13 C14 C15 C31 -176.1(7) . . . . ?
C30 C14 C15 C31 -3.8(11) . . . . ?
Ir1 C14 C15 C31 122.3(7) . . . . ?
C13 C14 C15 Ir1 61.6(4) . . . . ?
C30 C14 C15 Ir1 -126.0(7) . . . . ?
C12 C11 C15 C14 -1.3(7) . . . . ?
C16 C11 C15 C14 -178.0(6) . . . . ?
Ir1 C11 C15 C14 59.7(4) . . . . ?
C12 C11 C15 C31 176.8(7) . . . . ?
C16 C11 C15 C31 0.1(11) . . . . ?
Ir1 C11 C15 C31 -122.2(7) . . . . ?
C12 C11 C15 Ir1 -61.0(4) . . . . ?
C16 C11 C15 Ir1 122.3(6) . . . . ?
N2 Ir1 C15 C14 -147.1(4) . . . . ?
N1 Ir1 C15 C14 38.6(6) . . . . ?
C12 Ir1 C15 C14 -79.4(4) . . . . ?
C11 Ir1 C15 C14 -117.8(6) . . . . ?
C13 Ir1 C15 C14 -36.8(4) . . . . ?
Cl3 Ir1 C15 C14 124.5(4) . . . . ?
N2 Ir1 C15 C11 -29.3(6) . . . . ?
N1 Ir1 C15 C11 156.5(4) . . . . ?
C12 Ir1 C15 C11 38.4(4) . . . . ?
C14 Ir1 C15 C11 117.8(6) . . . . ?
C13 Ir1 C15 C11 81.0(4) . . . . ?
Cl3 Ir1 C15 C11 -117.7(4) . . . . ?
N2 Ir1 C15 C31 91.5(8) . . . . ?
N1 Ir1 C15 C31 -82.8(8) . . . . ?
C12 Ir1 C15 C31 159.2(8) . . . . ?
C11 Ir1 C15 C31 120.7(9) . . . . ?
C14 Ir1 C15 C31 -121.4(9) . . . . ?
C13 Ir1 C15 C31 -158.2(8) . . . . ?
Cl3 Ir1 C15 C31 3.0(7) . . . . ?
C12 C11 C16 C21 130.6(7) . . . . ?
C15 C11 C16 C21 -53.4(10) . . . . ?
Ir1 C11 C16 C21 39.6(9) . . . . ?
C12 C11 C16 C17 -49.8(9) . . . . ?
C15 C11 C16 C17 126.2(7) . . . . ?
Ir1 C11 C16 C17 -140.9(6) . . . . ?
C21 C16 C17 C18 -1.7(11) . . . . ?
C11 C16 C17 C18 178.8(6) . . . . ?
C16 C17 C18 C19 0.4(11) . . . . ?
C17 C18 C19 C20 1.5(11) . . . . ?
C17 C18 C19 C22 -175.5(7) . . . . ?
C18 C19 C20 C21 -2.3(11) . . . . ?
C22 C19 C20 C21 174.9(6) . . . . ?
C17 C16 C21 C20 0.9(11) . . . . ?
C11 C16 C21 C20 -179.5(7) . . . . ?
C19 C20 C21 C16 1.1(11) . . . . ?
C20 C19 C22 C23 -141.6(7) . . . . ?
C18 C19 C22 C23 35.4(10) . . . . ?
C20 C19 C22 C27 37.7(10) . . . . ?
C18 C19 C22 C27 -145.3(7) . . . . ?
C27 C22 C23 C24 -3.8(12) . . . . ?
C19 C22 C23 C24 175.5(8) . . . . ?
C22 C23 C24 C25 1.9(14) . . . . ?
C23 C24 C25 C26 0.7(13) . . . . ?
C24 C25 C26 C27 -1.3(12) . . . . ?
C25 C26 C27 C22 -0.6(11) . . . . ?
C23 C22 C27 C26 3.1(11) . . . . ?
C19 C22 C27 C26 -176.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.240
_refine_diff_density_min         -1.329
_refine_diff_density_rms         0.127
####################################################################### 
# 
# 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_180405j_sq
_database_code_depnum_ccdc_archive 'CCDC 1569686'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-09-04 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            'C31 H31 Cl F6 Ir N4 P'
_chemical_formula_weight         832.22

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.1500(9)
_cell_length_b                   13.1501(11)
_cell_length_c                   14.9502(12)
_cell_angle_alpha                104.382(2)
_cell_angle_beta                 104.100(2)
_cell_angle_gamma                105.659(3)
_cell_volume                     1754.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3583
_cell_measurement_theta_min      2.619
_cell_measurement_theta_max      24.615

_exptl_crystal_description       block
_exptl_crystal_colour            organge
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    3.983
_shelx_estimated_absorpt_T_min   0.381
_shelx_estimated_absorpt_T_max   0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3812
_exptl_absorpt_correction_T_max  0.4610
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            8706
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.619
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_full        25.017
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             6072
_reflns_number_gt                4667
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1190P)²] 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         6072
_refine_ls_number_parameters     420
_refine_ls_number_restraints     147
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   0.696
_refine_ls_restrained_S_all      0.718
_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 0.36509(3) 0.25603(2) 0.65345(2) 0.04099(12) Uani 1 1 d . . . . .
Cl1 Cl 0.2051(2) 0.06399(15) 0.56932(16) 0.0568(5) Uani 1 1 d . . . . .
F1 F 0.5788(19) 0.2697(14) 0.1977(10) 0.153(4) Uani 0.667(7) 1 d . U P A 1
F2 F 0.401(2) 0.1303(12) -0.0184(9) 0.155(4) Uani 0.667(7) 1 d . U P A 1
F3 F 0.6099(19) 0.1945(13) 0.0609(12) 0.177(4) Uani 0.667(7) 1 d . U P A 1
F4 F 0.498(2) 0.3133(12) 0.0643(11) 0.174(4) Uani 0.667(7) 1 d . U P A 1
F5 F 0.3398(18) 0.2074(15) 0.1341(12) 0.172(4) Uani 0.667(7) 1 d . U P A 1
F6 F 0.448(2) 0.0866(13) 0.1066(11) 0.165(4) Uani 0.667(7) 1 d . U P A 1
F1' F 0.588(4) 0.154(3) 0.1415(18) 0.153(4) Uani 0.333(7) 1 d . . P A 2
F2' F 0.356(3) 0.289(2) 0.0745(17) 0.155(4) Uani 0.333(7) 1 d D . P A 2
F3' F 0.301(4) 0.119(2) 0.0028(19) 0.177(4) Uani 0.333(7) 1 d D . P A 2
F4' F 0.410(4) 0.145(2) 0.153(2) 0.174(4) Uani 0.333(7) 1 d D . P A 2
F5' F 0.557(4) 0.307(3) 0.172(2) 0.172(4) Uani 0.333(7) 1 d D . P A 2
F6' F 0.509(3) 0.230(2) 0.0162(19) 0.165(4) Uani 0.333(7) 1 d D . P A 2
P1 P 0.4637(5) 0.2002(3) 0.0878(2) 0.1123(12) Uani 1 1 d . U . . .
N1 N 0.5148(6) 0.1864(5) 0.7119(4) 0.0417(13) Uani 1 1 d . . . . .
N2 N 0.4639(6) 0.2247(4) 0.5465(4) 0.0374(12) Uani 1 1 d . . . . .
N3 N 0.8099(9) 0.0389(7) 0.8097(6) 0.081(2) Uani 1 1 d . . . . .
H3A H 0.8239 0.0305 0.8661 0.098 Uiso 1 1 calc R U . . .
H3B H 0.8576 0.0172 0.7732 0.098 Uiso 1 1 calc R U . . .
N4 N 0.6470(9) 0.1268(6) 0.3356(5) 0.074(2) Uani 1 1 d . . . . .
H4A H 0.6225 0.1390 0.2811 0.089 Uiso 1 1 calc R U . . .
H4B H 0.7092 0.0941 0.3463 0.089 Uiso 1 1 calc R U . . .
C1 C 0.5373(9) 0.1692(6) 0.8005(5) 0.0480(18) Uani 1 1 d . . . . .
H1 H 0.4833 0.1909 0.8388 0.058 Uiso 1 1 calc R U . . .
C2 C 0.6341(10) 0.1220(7) 0.8359(6) 0.059(2) Uani 1 1 d . . . . .
H2 H 0.6472 0.1140 0.8972 0.071 Uiso 1 1 calc R U . . .
C3 C 0.7124(9) 0.0863(6) 0.7782(6) 0.0526(19) Uani 1 1 d . . . . .
C4 C 0.6873(8) 0.1013(6) 0.6869(5) 0.0435(16) Uani 1 1 d . . . . .
H4 H 0.7375 0.0776 0.6464 0.052 Uiso 1 1 calc R U . . .
C5 C 0.5900(7) 0.1503(5) 0.6565(5) 0.0376(15) Uani 1 1 d . . . . .
C6 C 0.5607(7) 0.1713(5) 0.5615(5) 0.0355(14) Uani 1 1 d . . . . .
C7 C 0.6229(8) 0.1383(6) 0.4946(5) 0.0445(17) Uani 1 1 d . . . . .
H7 H 0.6887 0.1021 0.5077 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5880(8) 0.1587(6) 0.4042(5) 0.0461(17) Uani 1 1 d . . . . .
C9 C 0.4857(9) 0.2123(6) 0.3876(5) 0.0511(19) Uani 1 1 d . . . . .
H9 H 0.4570 0.2256 0.3289 0.061 Uiso 1 1 calc R U . . .
C10 C 0.4299(9) 0.2441(6) 0.4600(6) 0.0532(19) Uani 1 1 d . . . . .
H10 H 0.3647 0.2814 0.4495 0.064 Uiso 1 1 calc R U . . .
C11 C 0.2695(8) 0.3800(6) 0.6295(5) 0.0463(18) Uani 1 1 d . . . . .
C12 C 0.4164(8) 0.4335(6) 0.6941(5) 0.0436(16) Uani 1 1 d . . . . .
C13 C 0.4231(9) 0.4008(6) 0.7804(5) 0.0523(19) Uani 1 1 d . . . . .
C14 C 0.2830(10) 0.3236(7) 0.7662(5) 0.054(2) Uani 1 1 d . . . . .
C15 C 0.1888(9) 0.3139(6) 0.6738(6) 0.0491(18) Uani 1 1 d . . . . .
C16 C 0.2052(7) 0.4034(5) 0.5364(5) 0.0396(15) Uani 1 1 d . . . . .
C17 C 0.2330(8) 0.5132(6) 0.5401(5) 0.0478(17) Uani 1 1 d . . . . .
H17 H 0.2896 0.5711 0.5987 0.057 Uiso 1 1 calc R U . . .
C18 C 0.1770(9) 0.5385(6) 0.4565(6) 0.0525(19) Uani 1 1 d . . . . .
H18 H 0.1959 0.6133 0.4614 0.063 Uiso 1 1 calc R U . . .
C19 C 0.0953(8) 0.4570(6) 0.3677(6) 0.0507(18) Uani 1 1 d . . . . .
C20 C 0.0628(9) 0.3467(6) 0.3651(6) 0.058(2) Uani 1 1 d . . . . .
H20 H 0.0020 0.2890 0.3073 0.069 Uiso 1 1 calc R U . . .
C21 C 0.1204(8) 0.3203(6) 0.4487(6) 0.0506(19) Uani 1 1 d . . . . .
H21 H 0.1005 0.2456 0.4443 0.061 Uiso 1 1 calc R U . . .
C22 C 0.0424(9) 0.4843(7) 0.2768(6) 0.057(2) Uani 1 1 d . . . . .
C23 C 0.1310(11) 0.5674(7) 0.2557(6) 0.064(2) Uani 1 1 d . . . . .
H23 H 0.2239 0.6091 0.3001 0.077 Uiso 1 1 calc R U . . .
C24 C 0.0868(14) 0.5909(9) 0.1709(7) 0.084(3) Uani 1 1 d . . . . .
H24 H 0.1504 0.6458 0.1573 0.101 Uiso 1 1 calc R U . . .
C25 C -0.0504(15) 0.5333(10) 0.1071(7) 0.094(4) Uani 1 1 d . . . . .
H25 H -0.0807 0.5491 0.0499 0.113 Uiso 1 1 calc R U . . .
C26 C -0.1450(15) 0.4513(12) 0.1269(8) 0.106(4) Uani 1 1 d . . . . .
H26 H -0.2395 0.4127 0.0839 0.128 Uiso 1 1 calc R U . . .
C27 C -0.0966(11) 0.4272(9) 0.2124(7) 0.085(3) Uani 1 1 d . . . . .
H27 H -0.1594 0.3717 0.2258 0.102 Uiso 1 1 calc R U . . .
C28 C 0.5342(9) 0.5140(7) 0.6779(7) 0.062(2) Uani 1 1 d . . . . .
H28A H 0.5100 0.5040 0.6094 0.093 Uiso 1 1 calc R U . . .
H28B H 0.6232 0.5009 0.7002 0.093 Uiso 1 1 calc R U . . .
H28C H 0.5459 0.5891 0.7138 0.093 Uiso 1 1 calc R U . . .
C29 C 0.5546(12) 0.4446(8) 0.8702(6) 0.083(3) Uani 1 1 d . . . . .
H29A H 0.5592 0.3859 0.8969 0.125 Uiso 1 1 calc R U . . .
H29B H 0.5490 0.5059 0.9179 0.125 Uiso 1 1 calc R U . . .
H29C H 0.6401 0.4701 0.8532 0.125 Uiso 1 1 calc R U . . .
C30 C 0.2396(12) 0.2732(9) 0.8390(7) 0.083(3) Uani 1 1 d . . . . .
H30A H 0.2189 0.3264 0.8852 0.125 Uiso 1 1 calc R U . . .
H30B H 0.3175 0.2540 0.8729 0.125 Uiso 1 1 calc R U . . .
H30C H 0.1547 0.2068 0.8053 0.125 Uiso 1 1 calc R U . . .
C31 C 0.0270(10) 0.2426(8) 0.6285(7) 0.072(3) Uani 1 1 d . . . . .
H31A H 0.0141 0.1731 0.5813 0.107 Uiso 1 1 calc R U . . .
H31B H -0.0245 0.2825 0.5969 0.107 Uiso 1 1 calc R U . . .
H31C H -0.0099 0.2277 0.6790 0.107 Uiso 1 1 calc R U . . .


_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 N2 2.100(5) . ?
Ir1 N1 2.101(5) . ?
Ir1 C12 2.138(7) . ?
Ir1 C13 2.151(7) . ?
Ir1 C14 2.161(7) . ?
Ir1 C11 2.169(6) . ?
Ir1 C15 2.182(7) . ?
Ir1 Cl1 2.4103(19) . ?
F1 P1 1.626(15) . ?
F2 P1 1.495(13) . ?
F3 P1 1.645(16) . ?
F4 P1 1.579(13) . ?
F5 P1 1.589(16) . ?
F6 P1 1.561(13) . ?
F1' P1 1.67(3) . ?
F2' P1 1.81(3) . ?
F3' P1 1.68(3) . ?
F4' P1 1.47(3) . ?
F5' P1 1.51(3) . ?
F6' P1 1.37(2) . ?
N1 C5 1.343(8) . ?
N1 C1 1.374(9) . ?
N2 C6 1.360(8) . ?
N2 C10 1.361(9) . ?
N3 C3 1.357(10) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C8 1.344(9) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C1 C2 1.367(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(10) . ?
C4 C5 1.367(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.488(9) . ?
C6 C7 1.352(9) . ?
C7 C8 1.421(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.413(10) . ?
C9 C10 1.368(11) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C15 1.425(10) . ?
C11 C12 1.430(10) . ?
C11 C16 1.528(10) . ?
C12 C13 1.451(10) . ?
C12 C28 1.481(11) . ?
C13 C14 1.436(12) . ?
C13 C29 1.498(12) . ?
C14 C15 1.429(11) . ?
C14 C30 1.500(11) . ?
C15 C31 1.532(12) . ?
C16 C21 1.372(10) . ?
C16 C17 1.380(9) . ?
C17 C18 1.399(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(10) . ?
C19 C22 1.501(11) . ?
C20 C21 1.412(10) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.371(12) . ?
C22 C27 1.375(12) . ?
C23 C24 1.378(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(15) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(16) . ?
C25 H25 0.9300 . ?
C26 C27 1.398(13) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

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
N2 Ir1 N1 76.5(2) . . ?
N2 Ir1 C12 102.1(2) . . ?
N1 Ir1 C12 121.5(3) . . ?
N2 Ir1 C13 131.0(3) . . ?
N1 Ir1 C13 98.1(3) . . ?
C12 Ir1 C13 39.5(3) . . ?
N2 Ir1 C14 168.3(3) . . ?
N1 Ir1 C14 108.4(2) . . ?
C12 Ir1 C14 66.2(3) . . ?
C13 Ir1 C14 38.9(3) . . ?
N2 Ir1 C11 106.6(2) . . ?
N1 Ir1 C11 160.1(3) . . ?
C12 Ir1 C11 38.8(3) . . ?
C13 Ir1 C11 64.7(3) . . ?
C14 Ir1 C11 65.1(3) . . ?
N2 Ir1 C15 138.7(3) . . ?
N1 Ir1 C15 144.5(3) . . ?
C12 Ir1 C15 64.8(3) . . ?
C13 Ir1 C15 64.0(3) . . ?
C14 Ir1 C15 38.4(3) . . ?
C11 Ir1 C15 38.2(3) . . ?
N2 Ir1 Cl1 84.68(16) . . ?
N1 Ir1 Cl1 84.87(17) . . ?
C12 Ir1 Cl1 153.6(2) . . ?
C13 Ir1 Cl1 144.0(2) . . ?
C14 Ir1 Cl1 106.1(2) . . ?
C11 Ir1 Cl1 114.8(2) . . ?
C15 Ir1 Cl1 93.1(2) . . ?
F6' P1 F4' 168.8(19) . . ?
F6' P1 F5' 97.8(12) . . ?
F4' P1 F5' 92.0(11) . . ?
F2 P1 F6 85.3(8) . . ?
F2 P1 F4 92.5(8) . . ?
F6 P1 F4 172.1(11) . . ?
F2 P1 F5 111.6(10) . . ?
F6 P1 F5 87.4(9) . . ?
F4 P1 F5 100.5(10) . . ?
F2 P1 F1 161.1(10) . . ?
F6 P1 F1 91.1(8) . . ?
F4 P1 F1 88.4(8) . . ?
F5 P1 F1 86.8(8) . . ?
F2 P1 F3 77.9(9) . . ?
F6 P1 F3 87.9(10) . . ?
F4 P1 F3 84.2(10) . . ?
F5 P1 F3 169.0(9) . . ?
F1 P1 F3 83.4(9) . . ?
F6' P1 F1' 104.6(17) . . ?
F4' P1 F1' 71.4(18) . . ?
F5' P1 F1' 81.5(16) . . ?
F6' P1 F3' 89.1(10) . . ?
F4' P1 F3' 85.1(11) . . ?
F5' P1 F3' 149.3(16) . . ?
F1' P1 F3' 125.7(14) . . ?
F6' P1 F2' 85.3(17) . . ?
F4' P1 F2' 102(2) . . ?
F5' P1 F2' 78.4(10) . . ?
F1' P1 F2' 158.7(12) . . ?
F3' P1 F2' 72.4(9) . . ?
C5 N1 C1 116.8(6) . . ?
C5 N1 Ir1 117.7(4) . . ?
C1 N1 Ir1 125.4(5) . . ?
C6 N2 C10 117.5(6) . . ?
C6 N2 Ir1 116.8(4) . . ?
C10 N2 Ir1 125.4(5) . . ?
C3 N3 H3A 120.0 . . ?
C3 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C8 N4 H4A 120.0 . . ?
C8 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 C1 N1 124.0(7) . . ?
C2 C1 H1 118.0 . . ?
N1 C1 H1 118.0 . . ?
C1 C2 C3 118.5(7) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
N3 C3 C2 121.0(7) . . ?
N3 C3 C4 121.4(7) . . ?
C2 C3 C4 117.6(7) . . ?
C5 C4 C3 120.8(6) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 122.2(6) . . ?
N1 C5 C6 114.2(6) . . ?
C4 C5 C6 123.6(6) . . ?
C7 C6 N2 122.6(6) . . ?
C7 C6 C5 122.9(6) . . ?
N2 C6 C5 114.5(5) . . ?
C6 C7 C8 120.2(6) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N4 C8 C9 120.5(7) . . ?
N4 C8 C7 122.0(7) . . ?
C9 C8 C7 117.4(6) . . ?
C10 C9 C8 118.3(7) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
N2 C10 C9 124.0(7) . . ?
N2 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
C15 C11 C12 108.4(6) . . ?
C15 C11 C16 125.5(7) . . ?
C12 C11 C16 125.6(7) . . ?
C15 C11 Ir1 71.4(4) . . ?
C12 C11 Ir1 69.5(4) . . ?
C16 C11 Ir1 131.7(5) . . ?
C11 C12 C13 106.8(7) . . ?
C11 C12 C28 125.7(7) . . ?
C13 C12 C28 127.4(7) . . ?
C11 C12 Ir1 71.8(4) . . ?
C13 C12 Ir1 70.7(4) . . ?
C28 C12 Ir1 126.3(5) . . ?
C14 C13 C12 108.8(7) . . ?
C14 C13 C29 126.5(8) . . ?
C12 C13 C29 124.7(8) . . ?
C14 C13 Ir1 70.9(4) . . ?
C12 C13 Ir1 69.7(4) . . ?
C29 C13 Ir1 126.9(5) . . ?
C15 C14 C13 106.6(7) . . ?
C15 C14 C30 126.4(8) . . ?
C13 C14 C30 126.6(8) . . ?
C15 C14 Ir1 71.6(4) . . ?
C13 C14 Ir1 70.2(4) . . ?
C30 C14 Ir1 128.2(6) . . ?
C11 C15 C14 109.3(7) . . ?
C11 C15 C31 125.1(7) . . ?
C14 C15 C31 125.6(7) . . ?
C11 C15 Ir1 70.4(4) . . ?
C14 C15 Ir1 70.0(4) . . ?
C31 C15 Ir1 125.3(5) . . ?
C21 C16 C17 117.9(6) . . ?
C21 C16 C11 123.3(6) . . ?
C17 C16 C11 118.7(6) . . ?
C16 C17 C18 120.7(7) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 122.3(7) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C20 116.8(7) . . ?
C18 C19 C22 122.3(7) . . ?
C20 C19 C22 121.0(7) . . ?
C19 C20 C21 121.2(7) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C16 C21 C20 121.0(7) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C27 117.9(8) . . ?
C23 C22 C19 121.1(8) . . ?
C27 C22 C19 121.0(8) . . ?
C22 C23 C24 122.1(9) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C25 C24 C23 119.6(10) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.3(9) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 119.0(11) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
C22 C27 C26 121.0(11) . . ?
C22 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C12 C28 H28A 109.5 . . ?
C12 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C12 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C13 C29 H29A 109.5 . . ?
C13 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C13 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C14 C30 H30A 109.5 . . ?
C14 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C14 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C15 C31 H31A 109.5 . . ?
C15 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C15 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C5 N1 C1 C2 2.5(12) . . . . ?
Ir1 N1 C1 C2 178.9(6) . . . . ?
N1 C1 C2 C3 -1.8(13) . . . . ?
C1 C2 C3 N3 -179.9(8) . . . . ?
C1 C2 C3 C4 0.1(12) . . . . ?
N3 C3 C4 C5 -179.3(8) . . . . ?
C2 C3 C4 C5 0.6(12) . . . . ?
C1 N1 C5 C4 -1.7(10) . . . . ?
Ir1 N1 C5 C4 -178.4(5) . . . . ?
C1 N1 C5 C6 179.9(6) . . . . ?
Ir1 N1 C5 C6 3.2(7) . . . . ?
C3 C4 C5 N1 0.2(11) . . . . ?
C3 C4 C5 C6 178.5(7) . . . . ?
C10 N2 C6 C7 0.3(10) . . . . ?
Ir1 N2 C6 C7 174.6(5) . . . . ?
C10 N2 C6 C5 -178.6(6) . . . . ?
Ir1 N2 C6 C5 -4.2(7) . . . . ?
N1 C5 C6 C7 -178.1(6) . . . . ?
C4 C5 C6 C7 3.5(11) . . . . ?
N1 C5 C6 N2 0.7(8) . . . . ?
C4 C5 C6 N2 -177.7(6) . . . . ?
N2 C6 C7 C8 -0.1(11) . . . . ?
C5 C6 C7 C8 178.6(6) . . . . ?
C6 C7 C8 N4 -179.7(7) . . . . ?
C6 C7 C8 C9 -1.0(11) . . . . ?
N4 C8 C9 C10 -179.4(7) . . . . ?
C7 C8 C9 C10 1.9(11) . . . . ?
C6 N2 C10 C9 0.8(11) . . . . ?
Ir1 N2 C10 C9 -173.0(6) . . . . ?
C8 C9 C10 N2 -1.8(12) . . . . ?
C15 C11 C12 C13 -1.4(7) . . . . ?
C16 C11 C12 C13 170.3(6) . . . . ?
Ir1 C11 C12 C13 -62.5(4) . . . . ?
C15 C11 C12 C28 -176.8(7) . . . . ?
C16 C11 C12 C28 -5.1(11) . . . . ?
Ir1 C11 C12 C28 122.1(7) . . . . ?
C15 C11 C12 Ir1 61.1(5) . . . . ?
C16 C11 C12 Ir1 -127.3(6) . . . . ?
C11 C12 C13 C14 2.8(7) . . . . ?
C28 C12 C13 C14 178.1(7) . . . . ?
Ir1 C12 C13 C14 -60.4(5) . . . . ?
C11 C12 C13 C29 -175.3(7) . . . . ?
C28 C12 C13 C29 0.1(12) . . . . ?
Ir1 C12 C13 C29 121.6(7) . . . . ?
C11 C12 C13 Ir1 63.1(4) . . . . ?
C28 C12 C13 Ir1 -121.5(7) . . . . ?
C12 C13 C14 C15 -3.1(8) . . . . ?
C29 C13 C14 C15 174.9(7) . . . . ?
Ir1 C13 C14 C15 -62.7(5) . . . . ?
C12 C13 C14 C30 -176.8(7) . . . . ?
C29 C13 C14 C30 1.2(12) . . . . ?
Ir1 C13 C14 C30 123.5(8) . . . . ?
C12 C13 C14 Ir1 59.7(5) . . . . ?
C29 C13 C14 Ir1 -122.3(8) . . . . ?
C12 C11 C15 C14 -0.5(8) . . . . ?
C16 C11 C15 C14 -172.2(6) . . . . ?
Ir1 C11 C15 C14 59.4(5) . . . . ?
C12 C11 C15 C31 -179.8(6) . . . . ?
C16 C11 C15 C31 8.5(11) . . . . ?
Ir1 C11 C15 C31 -119.9(7) . . . . ?
C12 C11 C15 Ir1 -59.9(5) . . . . ?
C16 C11 C15 Ir1 128.4(7) . . . . ?
C13 C14 C15 C11 2.2(8) . . . . ?
C30 C14 C15 C11 176.0(7) . . . . ?
Ir1 C14 C15 C11 -59.6(5) . . . . ?
C13 C14 C15 C31 -178.5(6) . . . . ?
C30 C14 C15 C31 -4.8(12) . . . . ?
Ir1 C14 C15 C31 119.7(7) . . . . ?
C13 C14 C15 Ir1 61.8(5) . . . . ?
C30 C14 C15 Ir1 -124.4(8) . . . . ?
C15 C11 C16 C21 -56.2(10) . . . . ?
C12 C11 C16 C21 133.5(8) . . . . ?
Ir1 C11 C16 C21 40.0(11) . . . . ?
C15 C11 C16 C17 123.6(8) . . . . ?
C12 C11 C16 C17 -46.7(10) . . . . ?
Ir1 C11 C16 C17 -140.2(7) . . . . ?
C21 C16 C17 C18 -0.5(11) . . . . ?
C11 C16 C17 C18 179.7(7) . . . . ?
C16 C17 C18 C19 -1.2(12) . . . . ?
C17 C18 C19 C20 3.7(12) . . . . ?
C17 C18 C19 C22 -176.4(8) . . . . ?
C18 C19 C20 C21 -4.5(12) . . . . ?
C22 C19 C20 C21 175.6(8) . . . . ?
C17 C16 C21 C20 -0.3(11) . . . . ?
C11 C16 C21 C20 179.5(7) . . . . ?
C19 C20 C21 C16 2.9(13) . . . . ?
C18 C19 C22 C23 42.3(12) . . . . ?
C20 C19 C22 C23 -137.8(9) . . . . ?
C18 C19 C22 C27 -137.4(9) . . . . ?
C20 C19 C22 C27 42.5(12) . . . . ?
C27 C22 C23 C24 -2.9(13) . . . . ?
C19 C22 C23 C24 177.4(8) . . . . ?
C22 C23 C24 C25 2.4(15) . . . . ?
C23 C24 C25 C26 -0.2(17) . . . . ?
C24 C25 C26 C27 -1.2(19) . . . . ?
C23 C22 C27 C26 1.4(15) . . . . ?
C19 C22 C27 C26 -178.9(10) . . . . ?
C25 C26 C27 C22 0.6(19) . . . . ?

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
C9 H9 F4' 0.93 2.45 3.23(3) 142.1 .
C7 H7 Cl1 0.93 2.81 3.618(7) 146.2 2_656
C2 H2 F6 0.93 2.53 3.040(15) 114.6 2_656
C2 H2 F3 0.93 2.58 3.350(16) 140.9 1_556
C1 H1 F6' 0.93 2.51 3.23(3) 134.4 1_556
N4 H4B Cl1 0.86 2.90 3.651(8) 146.7 2_656
N4 H4A F4' 0.86 2.55 3.28(3) 143.3 .
N4 H4A F1' 0.86 2.10 2.95(3) 169.6 .
N4 H4A F6 0.86 2.57 3.353(17) 151.4 .
N4 H4A F1 0.86 2.43 3.194(16) 147.9 .

_refine_diff_density_max         1.068
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.115



