# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_gy215-sr
_database_code_depnum_ccdc_archive 'CCDC 1483570'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2016-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
"bis(2-phenyl-1H-benzo[d]imidazole-κ²N,C)-{methyl 1-butyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxylate-κ²N,N'}iridium(III) hexafluorophosphate tris(dichloromethane) solvate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H37 Ir N7 O2, F6 P, 3(C H2 Cl2)'
_chemical_formula_sum            'C47 H43 Cl6 F6 Ir N7 O2 P'
_chemical_formula_weight         1287.75

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   22.1254(11)
_cell_length_b                   16.4448(9)
_cell_length_c                   28.2843(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10291.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9634
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.33

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_F_000             5104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    3.005
_shelx_estimated_absorpt_T_min   0.498
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5547
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            230408
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_full        25.242
_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             10495
_reflns_number_gt                9542
_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 SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2009)'
_computing_publication_material  ?

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0163P)²+179.5196P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10495
_refine_ls_number_parameters     639
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_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
Ir Ir 0.45436(2) 0.40610(2) 0.18904(2) 0.01467(8) Uani 1 1 d . . . . .
N1 N 0.3842(2) 0.4367(3) 0.2330(2) 0.0160(12) Uani 1 1 d . . . . .
N2 N 0.3495(3) 0.4548(4) 0.3052(2) 0.0222(13) Uani 1 1 d . . . . .
H2 H 0.348(4) 0.457(6) 0.333(3) 0.033 Uiso 1 1 d . U . . .
N3 N 0.5270(3) 0.3600(3) 0.1525(2) 0.0181(12) Uani 1 1 d . . . . .
N4 N 0.5760(3) 0.2531(4) 0.1251(2) 0.0220(13) Uani 1 1 d . . . . .
H4 H 0.581(4) 0.206(6) 0.117(3) 0.033 Uiso 1 1 d . U . . .
N5 N 0.4126(3) 0.4414(4) 0.1248(2) 0.0193(12) Uani 1 1 d . . . . .
N6 N 0.3836(3) 0.5377(4) 0.0741(2) 0.0296(15) Uani 1 1 d . . . . .
N7 N 0.4752(2) 0.5332(3) 0.1827(2) 0.0172(12) Uani 1 1 d . . . . .
C1 C 0.3230(3) 0.4542(4) 0.2294(3) 0.0196(15) Uani 1 1 d . . . . .
C2 C 0.2844(3) 0.4597(4) 0.1908(3) 0.0224(15) Uani 1 1 d . . . . .
H2A H 0.2988 0.4524 0.1595 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2239(3) 0.4762(5) 0.1998(3) 0.0293(18) Uani 1 1 d . . . . .
H3 H 0.1964 0.4800 0.1741 0.035 Uiso 1 1 calc R U . . .
C4 C 0.2031(3) 0.4874(4) 0.2453(3) 0.0281(17) Uani 1 1 d . . . . .
H4A H 0.1614 0.4988 0.2499 0.034 Uiso 1 1 calc R U . . .
C5 C 0.2404(3) 0.4827(4) 0.2845(3) 0.0254(17) Uani 1 1 d . . . . .
H5 H 0.2256 0.4905 0.3157 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3010(3) 0.4657(4) 0.2754(3) 0.0217(15) Uani 1 1 d . . . . .
C7 C 0.3984(3) 0.4375(4) 0.2785(3) 0.0180(14) Uani 1 1 d . . . . .
C8 C 0.4598(3) 0.4177(4) 0.2919(3) 0.0183(14) Uani 1 1 d . . . . .
C9 C 0.4949(3) 0.3929(4) 0.2527(3) 0.0161(14) Uani 1 1 d . . . . .
C10 C 0.5544(3) 0.3716(5) 0.2622(3) 0.0232(15) Uani 1 1 d . . . . .
H10 H 0.5801 0.3554 0.2370 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5773(3) 0.3737(4) 0.3080(3) 0.0260(16) Uani 1 1 d . . . . .
H11 H 0.6175 0.3559 0.3137 0.031 Uiso 1 1 calc R U . . .
C12 C 0.5422(4) 0.4014(5) 0.3458(3) 0.0276(16) Uani 1 1 d . . . . .
H12 H 0.5592 0.4061 0.3765 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4833(3) 0.4216(5) 0.3380(3) 0.0242(16) Uani 1 1 d . . . . .
H13 H 0.4583 0.4382 0.3635 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5795(3) 0.3880(4) 0.1315(2) 0.0172(14) Uani 1 1 d . . . . .
C15 C 0.6027(3) 0.4652(5) 0.1258(3) 0.0226(15) Uani 1 1 d . . . . .
H15 H 0.5820 0.5115 0.1376 0.027 Uiso 1 1 calc R U . . .
C16 C 0.6573(4) 0.4730(5) 0.1022(3) 0.0275(17) Uani 1 1 d . . . . .
H16 H 0.6740 0.5257 0.0977 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6886(3) 0.4051(5) 0.0849(3) 0.0269(16) Uani 1 1 d . . . . .
H17 H 0.7261 0.4126 0.0692 0.032 Uiso 1 1 calc R U . . .
C18 C 0.6658(3) 0.3275(5) 0.0901(3) 0.0277(17) Uani 1 1 d . . . . .
H18 H 0.6864 0.2813 0.0781 0.033 Uiso 1 1 calc R U . . .
C19 C 0.6107(3) 0.3204(4) 0.1140(3) 0.0209(15) Uani 1 1 d . . . . .
C20 C 0.5265(3) 0.2790(4) 0.1478(3) 0.0194(14) Uani 1 1 d . . . . .
C21 C 0.4748(3) 0.2349(4) 0.1660(3) 0.0182(14) Uani 1 1 d . . . . .
C22 C 0.4320(3) 0.2875(4) 0.1883(2) 0.0175(13) Uani 1 1 d . . . . .
C23 C 0.3792(3) 0.2497(4) 0.2047(3) 0.0202(15) Uani 1 1 d . . . . .
H23 H 0.3495 0.2817 0.2204 0.024 Uiso 1 1 calc R U . . .
C24 C 0.3690(3) 0.1677(4) 0.1989(3) 0.0243(16) Uani 1 1 d . . . . .
H24 H 0.3320 0.1448 0.2096 0.029 Uiso 1 1 calc R U . . .
C25 C 0.4118(4) 0.1178(4) 0.1776(3) 0.0257(17) Uani 1 1 d . . . . .
H25 H 0.4046 0.0611 0.1745 0.031 Uiso 1 1 calc R U . . .
C26 C 0.4656(3) 0.1516(4) 0.1609(3) 0.0211(15) Uani 1 1 d . . . . .
H26 H 0.4953 0.1184 0.1463 0.025 Uiso 1 1 calc R U . . .
C27 C 0.3783(3) 0.4046(5) 0.0895(3) 0.0217(15) Uani 1 1 d . . . . .
C28 C 0.3627(3) 0.3236(5) 0.0826(3) 0.0246(16) Uani 1 1 d . . . . .
H28 H 0.3762 0.2820 0.1034 0.030 Uiso 1 1 calc R U . . .
C29 C 0.3267(4) 0.3067(5) 0.0441(3) 0.0272(17) Uani 1 1 d . . . . .
C30 C 0.3067(4) 0.3678(6) 0.0131(3) 0.037(2) Uani 1 1 d . . . . .
H30 H 0.2814 0.3536 -0.0128 0.044 Uiso 1 1 calc R U . . .
C31 C 0.3230(4) 0.4475(6) 0.0193(3) 0.036(2) Uani 1 1 d . . . . .
H31 H 0.3100 0.4889 -0.0018 0.044 Uiso 1 1 calc R U . . .
C32 C 0.3595(4) 0.4648(5) 0.0582(3) 0.0295(17) Uani 1 1 d . . . . .
C33 C 0.4161(3) 0.5201(4) 0.1142(3) 0.0218(15) Uani 1 1 d . . . . .
C34 C 0.4516(3) 0.5737(4) 0.1451(3) 0.0205(15) Uani 1 1 d . . . . .
C35 C 0.5084(3) 0.5738(4) 0.2140(3) 0.0197(15) Uani 1 1 d . . . . .
H35 H 0.5244 0.5454 0.2404 0.024 Uiso 1 1 calc R U . . .
C36 C 0.5207(4) 0.6568(5) 0.2094(3) 0.0263(17) Uani 1 1 d . . . . .
H36 H 0.5442 0.6846 0.2324 0.032 Uiso 1 1 calc R U . . .
C37 C 0.4979(4) 0.6968(5) 0.1709(3) 0.0289(18) Uani 1 1 d . . . . .
H37 H 0.5062 0.7530 0.1666 0.035 Uiso 1 1 calc R U . . .
C38 C 0.4629(4) 0.6557(5) 0.1386(3) 0.0299(18) Uani 1 1 d . . . . .
H38 H 0.4466 0.6835 0.1120 0.036 Uiso 1 1 calc R U . . .
C39 C 0.3796(5) 0.6157(5) 0.0486(3) 0.040(2) Uani 1 1 d . . . . .
H39A H 0.3737 0.6607 0.0714 0.048 Uiso 1 1 calc R U . . .
H39B H 0.3447 0.6148 0.0267 0.048 Uiso 1 1 calc R U . . .
C40 C 0.4405(6) 0.6293(7) 0.0198(4) 0.061(3) Uani 1 1 d . . . . .
H40A H 0.4755 0.6144 0.0398 0.074 Uiso 1 1 calc R U . . .
H40B H 0.4407 0.5936 -0.0084 0.074 Uiso 1 1 calc R U . . .
C41 C 0.4463(7) 0.7182(9) 0.0043(5) 0.083(4) Uani 1 1 d . . . . .
H41A H 0.4108 0.7337 -0.0150 0.100 Uiso 1 1 calc R U . . .
H41B H 0.4474 0.7538 0.0325 0.100 Uiso 1 1 calc R U . . .
C42 C 0.5039(6) 0.7297(15) -0.0246(5) 0.124(8) Uani 1 1 d . . . . .
H42A H 0.5120 0.7880 -0.0284 0.185 Uiso 1 1 calc R U . . .
H42B H 0.4988 0.7046 -0.0558 0.185 Uiso 1 1 calc R U . . .
H42C H 0.5379 0.7041 -0.0081 0.185 Uiso 1 1 calc R U . . .
C43 C 0.3067(4) 0.2204(6) 0.0341(3) 0.037(2) Uani 1 1 d . . . . .
C44 C 0.3117(6) 0.0828(6) 0.0603(5) 0.071(4) Uani 1 1 d . . . . .
H44A H 0.3257 0.0515 0.0877 0.106 Uiso 1 1 calc R U . . .
H44B H 0.3318 0.0628 0.0317 0.106 Uiso 1 1 calc R U . . .
H44C H 0.2679 0.0764 0.0569 0.106 Uiso 1 1 calc R U . . .
O1 O 0.2772(3) 0.2004(4) 0.0005(2) 0.0493(18) Uani 1 1 d . . . . .
O2 O 0.3263(4) 0.1693(4) 0.0672(3) 0.0524(19) Uani 1 1 d . . . . .
P P 0.65419(10) 0.05754(13) 0.07261(8) 0.0292(5) Uani 1 1 d . . . . .
F1 F 0.6583(5) -0.0306(4) 0.0948(3) 0.119(4) Uani 1 1 d . . . . .
F2 F 0.7032(4) 0.0871(8) 0.1072(4) 0.146(5) Uani 1 1 d . . . . .
F3 F 0.6046(4) 0.0254(7) 0.0388(4) 0.119(4) Uani 1 1 d . . . . .
F4 F 0.6470(5) 0.1442(4) 0.0513(3) 0.100(3) Uani 1 1 d . . . . .
F5 F 0.7037(3) 0.0336(4) 0.0353(2) 0.0601(17) Uani 1 1 d . . . . .
F6 F 0.6056(3) 0.0800(3) 0.1128(2) 0.0624(19) Uani 1 1 d . . . . .
C45 C 0.1901(4) 0.1786(5) 0.2841(4) 0.042(2) Uani 1 1 d . . . . .
H45A H 0.1964 0.1628 0.3176 0.051 Uiso 1 1 calc R U . . .
H45B H 0.2186 0.1466 0.2645 0.051 Uiso 1 1 calc R U . . .
Cl1 Cl 0.11552(10) 0.15496(13) 0.26745(8) 0.0374(5) Uani 1 1 d . . . . .
Cl2 Cl 0.20634(11) 0.28248(15) 0.27759(10) 0.0492(6) Uani 1 1 d . . . . .
C46 C 0.6692(8) 0.7569(13) 0.1088(6) 0.127(8) Uani 1 1 d . . . . .
H46A H 0.7016 0.7350 0.0883 0.153 Uiso 1 1 calc R U . . .
H46B H 0.6795 0.8139 0.1166 0.153 Uiso 1 1 calc R U . . .
Cl3 Cl 0.6659(2) 0.7028(6) 0.1582(2) 0.192(4) Uani 1 1 d . . . . .
Cl4 Cl 0.6019(3) 0.7548(7) 0.0786(2) 0.223(5) Uani 1 1 d . . . . .
C47 C 0.2279(5) 0.2654(6) 0.1476(4) 0.048(2) Uani 1 1 d . . . . .
H47A H 0.2214 0.2964 0.1771 0.058 Uiso 1 1 calc R U . . .
H47B H 0.2716 0.2672 0.1402 0.058 Uiso 1 1 calc R U . . .
Cl5 Cl 0.18769(11) 0.31217(16) 0.10153(9) 0.0492(6) Uani 1 1 d . . . . .
Cl6 Cl 0.20591(13) 0.16307(16) 0.15667(10) 0.0538(6) 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
Ir C22 2.012(7) . ?
Ir C9 2.023(7) . ?
Ir N1 2.051(6) . ?
Ir N3 2.055(6) . ?
Ir N5 2.119(6) . ?
Ir N7 2.149(6) . ?
N1 C7 1.325(9) . ?
N1 C1 1.390(9) . ?
N2 C7 1.348(9) . ?
N2 C6 1.377(10) . ?
N2 H2 0.79(9) . ?
N3 C20 1.337(9) . ?
N3 C14 1.385(9) . ?
N4 C20 1.341(9) . ?
N4 C19 1.383(9) . ?
N4 H4 0.82(9) . ?
N5 C33 1.330(9) . ?
N5 C27 1.392(9) . ?
N6 C33 1.374(10) . ?
N6 C32 1.388(10) . ?
N6 C39 1.473(10) . ?
N7 C35 1.330(9) . ?
N7 C34 1.359(9) . ?
C1 C2 1.388(10) . ?
C1 C6 1.401(10) . ?
C2 C3 1.387(10) . ?
C2 H2A 0.9500 . ?
C3 C4 1.379(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(12) . ?
C4 H4A 0.9500 . ?
C5 C6 1.394(10) . ?
C5 H5 0.9500 . ?
C7 C8 1.447(10) . ?
C8 C13 1.405(10) . ?
C8 C9 1.414(10) . ?
C9 C10 1.390(10) . ?
C10 C11 1.390(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.364(11) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.378(10) . ?
C14 C19 1.400(10) . ?
C15 C16 1.385(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.402(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(11) . ?
C17 H17 0.9500 . ?
C18 C19 1.397(10) . ?
C18 H18 0.9500 . ?
C20 C21 1.450(9) . ?
C21 C26 1.392(10) . ?
C21 C22 1.429(10) . ?
C22 C23 1.404(10) . ?
C23 C24 1.378(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(10) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.390(10) . ?
C27 C32 1.392(11) . ?
C28 C29 1.378(11) . ?
C28 H28 0.9500 . ?
C29 C30 1.406(12) . ?
C29 C43 1.514(11) . ?
C30 C31 1.370(12) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(11) . ?
C31 H31 0.9500 . ?
C33 C34 1.468(10) . ?
C34 C38 1.384(10) . ?
C35 C36 1.397(10) . ?
C35 H35 0.9500 . ?
C36 C37 1.368(12) . ?
C36 H36 0.9500 . ?
C37 C38 1.377(11) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.591(15) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.532(18) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.525(18) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 O1 1.200(10) . ?
C43 O2 1.330(11) . ?
C44 O2 1.473(10) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
P F2 1.540(8) . ?
P F3 1.549(8) . ?
P F4 1.555(6) . ?
P F5 1.570(6) . ?
P F1 1.582(7) . ?
P F6 1.609(5) . ?
C45 Cl2 1.755(9) . ?
C45 Cl1 1.761(9) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 Cl3 1.66(2) . ?
C46 Cl4 1.72(2) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 Cl5 1.755(11) . ?
C47 Cl6 1.771(10) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?

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
C22 Ir C9 90.8(3) . . ?
C22 Ir N1 93.3(3) . . ?
C9 Ir N1 79.7(2) . . ?
C22 Ir N3 80.2(3) . . ?
C9 Ir N3 93.5(3) . . ?
N1 Ir N3 170.6(2) . . ?
C22 Ir N5 98.6(2) . . ?
C9 Ir N5 170.2(2) . . ?
N1 Ir N5 97.1(2) . . ?
N3 Ir N5 90.6(2) . . ?
C22 Ir N7 174.3(3) . . ?
C9 Ir N7 94.8(2) . . ?
N1 Ir N7 88.6(2) . . ?
N3 Ir N7 98.6(2) . . ?
N5 Ir N7 75.8(2) . . ?
C7 N1 C1 107.5(6) . . ?
C7 N1 Ir 114.4(4) . . ?
C1 N1 Ir 138.1(5) . . ?
C7 N2 C6 108.1(6) . . ?
C7 N2 H2 127(7) . . ?
C6 N2 H2 125(7) . . ?
C20 N3 C14 107.2(6) . . ?
C20 N3 Ir 114.3(5) . . ?
C14 N3 Ir 138.5(5) . . ?
C20 N4 C19 108.0(6) . . ?
C20 N4 H4 124(6) . . ?
C19 N4 H4 128(6) . . ?
C33 N5 C27 107.1(6) . . ?
C33 N5 Ir 115.7(5) . . ?
C27 N5 Ir 137.1(5) . . ?
C33 N6 C32 106.7(6) . . ?
C33 N6 C39 128.3(7) . . ?
C32 N6 C39 124.7(7) . . ?
C35 N7 C34 119.1(6) . . ?
C35 N7 Ir 123.5(5) . . ?
C34 N7 Ir 117.4(4) . . ?
C2 C1 N1 132.2(7) . . ?
C2 C1 C6 120.5(7) . . ?
N1 C1 C6 107.3(6) . . ?
C3 C2 C1 117.5(7) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C4 C3 C2 121.2(8) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 122.7(7) . . ?
C3 C4 H4A 118.6 . . ?
C5 C4 H4A 118.6 . . ?
C4 C5 C6 115.8(7) . . ?
C4 C5 H5 122.1 . . ?
C6 C5 H5 122.1 . . ?
N2 C6 C5 131.5(7) . . ?
N2 C6 C1 106.3(6) . . ?
C5 C6 C1 122.2(7) . . ?
N1 C7 N2 110.8(6) . . ?
N1 C7 C8 118.2(6) . . ?
N2 C7 C8 130.9(7) . . ?
C13 C8 C9 122.5(6) . . ?
C13 C8 C7 125.4(6) . . ?
C9 C8 C7 112.1(6) . . ?
C10 C9 C8 116.2(7) . . ?
C10 C9 Ir 128.3(6) . . ?
C8 C9 Ir 115.0(5) . . ?
C9 C10 C11 121.3(7) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 121.2(7) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.2(7) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 119.5(7) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C15 C14 N3 132.1(6) . . ?
C15 C14 C19 120.4(6) . . ?
N3 C14 C19 107.5(6) . . ?
C14 C15 C16 117.8(7) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C15 C16 C17 121.6(7) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 121.2(7) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 116.6(7) . . ?
C17 C18 H18 121.7 . . ?
C19 C18 H18 121.7 . . ?
N4 C19 C18 131.3(7) . . ?
N4 C19 C14 106.3(6) . . ?
C18 C19 C14 122.3(7) . . ?
N3 C20 N4 111.0(6) . . ?
N3 C20 C21 118.0(6) . . ?
N4 C20 C21 131.1(7) . . ?
C26 C21 C22 123.0(6) . . ?
C26 C21 C20 124.8(7) . . ?
C22 C21 C20 112.1(6) . . ?
C23 C22 C21 115.4(6) . . ?
C23 C22 Ir 129.1(5) . . ?
C21 C22 Ir 115.4(5) . . ?
C24 C23 C22 122.0(7) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 121.2(7) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 119.5(7) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C21 C26 C25 118.8(7) . . ?
C21 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C28 C27 C32 121.2(7) . . ?
C28 C27 N5 130.7(7) . . ?
C32 C27 N5 108.1(7) . . ?
C29 C28 C27 116.6(7) . . ?
C29 C28 H28 121.7 . . ?
C27 C28 H28 121.7 . . ?
C28 C29 C30 122.2(7) . . ?
C28 C29 C43 120.3(7) . . ?
C30 C29 C43 117.5(7) . . ?
C31 C30 C29 121.3(8) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 116.8(8) . . ?
C30 C31 H31 121.6 . . ?
C32 C31 H31 121.6 . . ?
N6 C32 C27 107.0(7) . . ?
N6 C32 C31 131.0(8) . . ?
C27 C32 C31 122.0(8) . . ?
N5 C33 N6 111.1(6) . . ?
N5 C33 C34 118.8(7) . . ?
N6 C33 C34 130.0(7) . . ?
N7 C34 C38 120.8(7) . . ?
N7 C34 C33 112.1(6) . . ?
C38 C34 C33 127.1(7) . . ?
N7 C35 C36 122.4(7) . . ?
N7 C35 H35 118.8 . . ?
C36 C35 H35 118.8 . . ?
C37 C36 C35 118.1(7) . . ?
C37 C36 H36 120.9 . . ?
C35 C36 H36 120.9 . . ?
C36 C37 C38 120.0(7) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C37 C38 C34 119.4(8) . . ?
C37 C38 H38 120.3 . . ?
C34 C38 H38 120.3 . . ?
N6 C39 C40 108.8(8) . . ?
N6 C39 H39A 109.9 . . ?
C40 C39 H39A 109.9 . . ?
N6 C39 H39B 109.9 . . ?
C40 C39 H39B 109.9 . . ?
H39A C39 H39B 108.3 . . ?
C41 C40 C39 110.6(10) . . ?
C41 C40 H40A 109.5 . . ?
C39 C40 H40A 109.5 . . ?
C41 C40 H40B 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 108.1 . . ?
C42 C41 C40 110.0(14) . . ?
C42 C41 H41A 109.7 . . ?
C40 C41 H41A 109.7 . . ?
C42 C41 H41B 109.7 . . ?
C40 C41 H41B 109.7 . . ?
H41A C41 H41B 108.2 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O1 C43 O2 124.3(9) . . ?
O1 C43 C29 124.3(9) . . ?
O2 C43 C29 111.4(7) . . ?
O2 C44 H44A 109.5 . . ?
O2 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
O2 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C43 O2 C44 116.4(8) . . ?
F2 P F3 178.2(8) . . ?
F2 P F4 91.6(7) . . ?
F3 P F4 90.1(6) . . ?
F2 P F5 90.9(4) . . ?
F3 P F5 89.6(4) . . ?
F4 P F5 92.4(4) . . ?
F2 P F1 89.8(7) . . ?
F3 P F1 88.4(6) . . ?
F4 P F1 177.4(5) . . ?
F5 P F1 89.8(4) . . ?
F2 P F6 87.1(4) . . ?
F3 P F6 92.4(5) . . ?
F4 P F6 89.7(3) . . ?
F5 P F6 177.1(4) . . ?
F1 P F6 88.2(3) . . ?
Cl2 C45 Cl1 112.2(5) . . ?
Cl2 C45 H45A 109.2 . . ?
Cl1 C45 H45A 109.2 . . ?
Cl2 C45 H45B 109.2 . . ?
Cl1 C45 H45B 109.2 . . ?
H45A C45 H45B 107.9 . . ?
Cl3 C46 Cl4 111.8(9) . . ?
Cl3 C46 H46A 109.3 . . ?
Cl4 C46 H46A 109.3 . . ?
Cl3 C46 H46B 109.3 . . ?
Cl4 C46 H46B 109.3 . . ?
H46A C46 H46B 107.9 . . ?
Cl5 C47 Cl6 112.6(6) . . ?
Cl5 C47 H47A 109.1 . . ?
Cl6 C47 H47A 109.1 . . ?
Cl5 C47 H47B 109.1 . . ?
Cl6 C47 H47B 109.1 . . ?
H47A C47 H47B 107.8 . . ?

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
N2 H2 F1 0.79(9) 2.06(9) 2.846(10) 176(10) 3_655
N4 H4 F4 0.82(9) 2.57(9) 3.167(9) 131(8) .
N4 H4 F6 0.82(9) 2.14(9) 2.941(8) 167(9) .
C18 H18 F4 0.95 2.53 3.235(11) 130.8 .
C31 H31 F5 0.95 2.56 3.075(10) 114.0 4_455
C39 H39A Cl5 0.99 2.96 3.860(10) 151.3 8_665
C39 H39A Cl6 0.99 2.99 3.677(11) 127.8 8_665
C44 H44B F5 0.98 2.59 3.330(13) 132.1 5_655
C45 H45A F2 0.99 2.47 3.433(13) 164.5 6_556
C47 H47A Cl2 0.99 2.87 3.719(12) 144.3 .

_refine_diff_density_max         2.309
_refine_diff_density_min         -3.618
_refine_diff_density_rms         0.159

_shelxl_version_number           2014-3


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.000 98 19 ' '
2 1.000 0.000 0.500 98 19 ' '
3 1.000 0.500 0.000 98 19 ' '
4 0.500 0.500 0.500 98 19 ' '
_platon_squeeze_details          
;
;

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'methylene chloride, hexane'
####################################################################### 
# 
# 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_gy200c_sq
_database_code_depnum_ccdc_archive 'CCDC 1483571'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2016-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"bis(1-phenyl-1H-pyrazole-κ²N,C)-{methyl 1-butyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxylate-κ²N,N'}iridium(III) hexafluorophosphate dichloromethane solvate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H29.50 Ir N7 O2, F6 P, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C35.50 H30.50 Cl F6 Ir N7 O2 P'
_chemical_formula_weight         959.79

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'
Ir Ir -1.4442 7.9887 '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'

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

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

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

_cell_length_a                   24.4157(10)
_cell_length_b                   16.5559(7)
_cell_length_c                   23.3462(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.7896(14)
_cell_angle_gamma                90
_cell_volume                     8635.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9344
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      30.50

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             3772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    3.254
_shelx_estimated_absorpt_T_min   0.577
_shelx_estimated_absorpt_T_max   0.624
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            260552
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.988
_diffrn_reflns_theta_max         26.049
_diffrn_reflns_theta_full        25.242
_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             8538
_reflns_number_gt                8151
_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 SMART (Bruker, 1997)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material  ?

_refine_special_details          'SQUEEZE,orientational ligand disorder'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+58.2454P] 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         8538
_refine_ls_number_parameters     676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Ir Ir 0.18028(2) 0.92390(2) 0.16476(2) 0.02794(6) Uani 1 1 d . . . . .
N1 N 0.24232(17) 0.9188(3) 0.12866(17) 0.0490(11) Uani 1 1 d . . . . .
C1A C 0.2462(8) 0.9399(7) 0.0733(8) 0.028(3) Uani 0.4 1 d . . P A 3
H1A H 0.2124 0.9517 0.0359 0.033 Uiso 0.4 1 calc R U P A 3
C2A C 0.3063(9) 0.9424(8) 0.0780(10) 0.037(3) Uani 0.4 1 d . . P A 3
H2A H 0.3203 0.9461 0.0456 0.045 Uiso 0.4 1 calc R U P A 3
C3A C 0.3393(13) 0.9379(10) 0.1433(14) 0.036(4) Uani 0.4 1 d . . P A 3
H3A H 0.3813 0.9458 0.1645 0.044 Uiso 0.4 1 calc R U P A 3
C1B C 0.2418(7) 0.9023(9) 0.0724(6) 0.063(4) Uani 0.6 1 d . . P A 4
H1B H 0.2075 0.8931 0.0348 0.076 Uiso 0.6 1 calc R U P A 4
C2B C 0.3010(8) 0.9010(13) 0.0796(8) 0.104(7) Uani 0.6 1 d . . P A 4
H2B H 0.3146 0.8977 0.0468 0.125 Uiso 0.6 1 calc R U P A 4
C3B C 0.3357(9) 0.9054(11) 0.1410(10) 0.072(6) Uani 0.6 1 d . . P A 4
H3B H 0.3780 0.8994 0.1597 0.087 Uiso 0.6 1 calc R U P A 4
N2 N 0.30015(16) 0.9198(3) 0.17166(18) 0.0477(10) Uani 1 1 d . . . . .
C4 C 0.30866(18) 0.9221(2) 0.23527(19) 0.0339(9) Uani 1 1 d . . . . .
C5 C 0.25560(18) 0.9261(2) 0.24454(18) 0.0312(9) Uani 1 1 d . . . . .
C6 C 0.2623(2) 0.9301(3) 0.3066(2) 0.0439(11) Uani 1 1 d . . . . .
H6 H 0.2279 0.9337 0.3157 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3192(2) 0.9289(3) 0.3558(2) 0.0510(13) Uani 1 1 d . . . . .
H7 H 0.3228 0.9315 0.3978 0.061 Uiso 1 1 calc R U . . .
C8 C 0.3699(2) 0.9240(3) 0.3440(2) 0.0443(12) Uani 1 1 d . . . . .
H8 H 0.4081 0.9227 0.3779 0.053 Uiso 1 1 calc R U . . .
C9 C 0.36569(19) 0.9208(2) 0.2833(2) 0.0380(10) Uani 1 1 d . . . . .
H9 H 0.4004 0.9179 0.2746 0.046 Uiso 1 1 calc R U . . .
N3 N 0.12661(16) 0.9402(3) 0.21007(16) 0.0487(11) Uani 1 1 d . . . . .
C10 C 0.1010(2) 0.8935(6) 0.2391(2) 0.083(2) Uani 1 1 d . . . . .
H10 H 0.0996 0.8361 0.2386 0.099 Uiso 1 1 calc R U . . .
C11 C 0.0767(4) 0.9449(10) 0.2704(4) 0.147(7) Uani 1 1 d . . . . .
H11 H 0.0559 0.9283 0.2950 0.176 Uiso 1 1 calc R U . . .
C12 C 0.0876(4) 1.0203(9) 0.2599(4) 0.128(6) Uani 1 1 d . . . . .
H12 H 0.0760 1.0674 0.2753 0.154 Uiso 1 1 calc R U . . .
N4 N 0.11866(19) 1.0177(4) 0.2227(2) 0.0722(19) Uani 1 1 d . . . . .
C13 C 0.1440(3) 1.0760(4) 0.1972(3) 0.075(2) Uani 1 1 d . . . . .
C14 C 0.1790(2) 1.0452(3) 0.1671(2) 0.0478(13) Uani 1 1 d . . . . .
C15 C 0.2043(3) 1.1028(4) 0.1420(3) 0.075(2) Uani 1 1 d . . . . .
H15 H 0.2299 1.0863 0.1224 0.090 Uiso 1 1 calc R U . . .
C16 C 0.1923(4) 1.1858(5) 0.1452(4) 0.111(4) Uani 1 1 d . . . . .
H16 H 0.2084 1.2242 0.1260 0.133 Uiso 1 1 calc R U . . .
C17 C 0.1588(7) 1.2112(7) 0.1750(6) 0.168(8) Uani 1 1 d . . . . .
H17 H 0.1528 1.2675 0.1781 0.201 Uiso 1 1 calc R U . . .
C18 C 0.1336(4) 1.1583(6) 0.2005(4) 0.125(5) Uani 1 1 d . . . . .
H18 H 0.1089 1.1766 0.2206 0.150 Uiso 1 1 calc R U . . .
N5 N 0.10927(15) 0.9056(2) 0.07487(16) 0.0378(9) Uani 1 1 d . . . . .
C19 C 0.08006(17) 0.9512(3) 0.02138(18) 0.0393(11) Uani 1 1 d . . . . .
C20 C 0.07858(19) 1.0329(4) 0.0126(2) 0.0516(14) Uani 1 1 d . . . . .
H20 H 0.0984 1.0690 0.0463 0.062 Uiso 1 1 calc R U . . .
C21 C 0.0465(2) 1.0607(5) -0.0482(2) 0.073(2) Uani 1 1 d . . . . .
C22 C 0.0167(2) 1.0058(6) -0.0975(2) 0.083(3) Uani 1 1 d . . . . .
H22 H -0.0050 1.0264 -0.1384 0.099 Uiso 1 1 calc R U . . .
C23 C 0.0181(3) 0.9265(6) -0.0885(3) 0.093(3) Uani 1 1 d . . . . .
H23 H -0.0021 0.8903 -0.1220 0.112 Uiso 1 1 calc R U . . .
C24 C 0.0504(2) 0.8990(4) -0.0282(2) 0.072(2) Uani 1 1 d . . . . .
N6A N 0.0718(3) 0.8351(5) -0.0129(3) 0.0291(14) Uani 0.5 1 d . . P B 1
C25A C 0.1060(4) 0.8393(6) 0.0510(4) 0.030(2) Uani 0.5 1 d . . P B 1
C26A C 0.1353(4) 0.7727(6) 0.0946(4) 0.0350(19) Uani 0.5 1 d . . P B 1
N6B N 0.0503(3) 0.8107(4) 0.0048(3) 0.0258(13) Uani 0.5 1 d . . P B 2
C25B C 0.0886(4) 0.8213(5) 0.0660(4) 0.0254(18) Uani 0.5 1 d . . P B 2
C26B C 0.1149(4) 0.7627(5) 0.1163(4) 0.0330(18) Uani 0.5 1 d . . P B 2
N7 N 0.1687(2) 0.7958(2) 0.1583(2) 0.0602(14) Uani 1 1 d . . . . .
C27 C 0.1995(3) 0.7447(3) 0.2032(3) 0.077(2) Uani 1 1 d . . . . .
H27 H 0.2223 0.7628 0.2447 0.092 Uiso 1 1 calc R U . C 1
C28A C 0.1975(5) 0.6648(7) 0.1877(5) 0.052(3) Uani 0.5 1 d . . P B 1
H28A H 0.2245 0.6281 0.2168 0.063 Uiso 0.5 1 calc R U P B 1
C29A C 0.1570(5) 0.6363(6) 0.1305(4) 0.054(3) Uani 0.5 1 d . . P B 1
H29A H 0.1503 0.5799 0.1236 0.065 Uiso 0.5 1 calc R U P B 1
C30A C 0.1260(4) 0.6912(6) 0.0832(4) 0.046(2) Uani 0.5 1 d . . P B 1
H30A H 0.0987 0.6724 0.0434 0.055 Uiso 0.5 1 calc R U P B 1
C31A C 0.0635(4) 0.7665(5) -0.0565(4) 0.0358(18) Uani 0.5 1 d . . P B 1
H31A H 0.0320 0.7807 -0.0978 0.043 Uiso 0.5 1 calc R U P B 1
H31B H 0.0495 0.7188 -0.0406 0.043 Uiso 0.5 1 calc R U P B 1
C32A C 0.1198(4) 0.7447(5) -0.0644(4) 0.0363(18) Uani 0.5 1 d . . P B 1
H32A H 0.1502 0.7267 -0.0235 0.044 Uiso 0.5 1 calc R U P B 1
H32B H 0.1111 0.6987 -0.0938 0.044 Uiso 0.5 1 calc R U P B 1
C33A C 0.1455(4) 0.8127(6) -0.0884(4) 0.040(2) Uani 0.5 1 d . . P B 1
H33A H 0.1548 0.8580 -0.0583 0.048 Uiso 0.5 1 calc R U P B 1
H33B H 0.1144 0.8317 -0.1286 0.048 Uiso 0.5 1 calc R U P B 1
C34A C 0.2011(7) 0.7925(10) -0.0985(7) 0.050(3) Uani 0.5 1 d . . P B 1
H34A H 0.2333 0.7777 -0.0585 0.075 Uiso 0.5 1 calc R U P B 1
H34B H 0.2133 0.8395 -0.1160 0.075 Uiso 0.5 1 calc R U P B 1
H34C H 0.1928 0.7470 -0.1277 0.075 Uiso 0.5 1 calc R U P B 1
C28B C 0.1765(7) 0.6640(8) 0.2155(6) 0.078(5) Uani 0.5 1 d . . P B 2
H28B H 0.1965 0.6344 0.2531 0.094 Uiso 0.5 1 calc R U P B 2
C29B C 0.1242(6) 0.6364(7) 0.1677(5) 0.073(4) Uani 0.5 1 d . . P B 2
H29B H 0.1092 0.5841 0.1701 0.088 Uiso 0.5 1 calc R U P B 2
C30B C 0.0942(5) 0.6855(6) 0.1170(4) 0.052(3) Uani 0.5 1 d . . P B 2
H30B H 0.0597 0.6663 0.0829 0.062 Uiso 0.5 1 calc R U P B 2
C31B C 0.0253(3) 0.7348(5) -0.0284(3) 0.0282(16) Uani 0.5 1 d . . P B 2
H31C H -0.0089 0.7475 -0.0683 0.034 Uiso 0.5 1 calc R U P B 2
H31D H 0.0100 0.7019 -0.0026 0.034 Uiso 0.5 1 calc R U P B 2
C32B C 0.0715(4) 0.6857(6) -0.0422(4) 0.044(2) Uani 0.5 1 d . . P B 2
C35A C 0.0362(4) 1.1655(6) -0.0536(4) 0.043(2) Uani 0.55 1 d . . P D 5
O1A O 0.0101(4) 1.1964(6) -0.1040(4) 0.083(3) Uani 0.55 1 d . . P D 5
O2A O 0.0617(3) 1.2080(4) -0.0008(3) 0.0526(16) Uani 0.55 1 d . . P D 5
C36A C 0.0589(6) 1.2949(6) -0.0062(5) 0.069(3) Uani 0.55 1 d . . P D 5
H36A H 0.0882 1.3137 -0.0221 0.104 Uiso 0.55 1 calc R U P D 5
H36B H 0.0679 1.3189 0.0350 0.104 Uiso 0.55 1 calc R U P D 5
H36C H 0.0186 1.3111 -0.0352 0.104 Uiso 0.55 1 calc R U P D 5
C35B C 0.0516(4) 1.1288(6) -0.0720(5) 0.031(2) Uani 0.45 1 d . . P D 6
O1B O 0.0256(3) 1.1526(4) -0.1262(3) 0.0419(17) Uani 0.45 1 d . . P D 6
O2B O 0.0830(3) 1.1775(4) -0.0254(3) 0.0366(15) Uani 0.45 1 d . . P D 6
C36B C 0.0886(5) 1.2598(6) -0.0409(6) 0.053(3) Uani 0.45 1 d . . P D 6
H36D H 0.1128 1.2623 -0.0658 0.079 Uiso 0.45 1 calc R U P D 6
H36E H 0.1082 1.2912 -0.0024 0.079 Uiso 0.45 1 calc R U P D 6
H36F H 0.0488 1.2822 -0.0653 0.079 Uiso 0.45 1 calc R U P D 6
P1 P 0.44468(11) 1.00333(15) 0.04554(11) 0.0407(5) Uani 0.5 1 d . . P . .
F1 F 0.4462(3) 1.0703(4) -0.0035(3) 0.0659(18) Uani 0.5 1 d . . P . .
F2 F 0.4075(3) 1.0637(4) 0.0691(4) 0.073(2) Uani 0.5 1 d . . P . .
F3 F 0.4455(3) 0.9285(6) 0.0885(4) 0.118(4) Uani 0.5 1 d . . P . .
F4 F 0.4826(3) 0.9427(4) 0.0243(4) 0.0717(19) Uani 0.5 1 d . . P . .
F5 F 0.5053(3) 1.0429(5) 0.0952(4) 0.082(2) Uani 0.5 1 d . . P . .
F6 F 0.3869(3) 0.9664(3) -0.0027(3) 0.0529(14) Uani 0.5 1 d . . P . .
P2 P 0.0000 0.72597(10) -0.2500 0.0336(3) Uani 1 2 d S T P . .
F7 F 0.07048(11) 0.7251(2) -0.21246(15) 0.0663(9) Uani 1 1 d . . . . .
F8 F 0.01080(15) 0.7252(3) -0.31138(15) 0.1007(16) Uani 1 1 d . . . . .
F9 F 0.0000 0.6317(3) -0.2500 0.141(4) Uani 1 2 d S T P . .
F10 F 0.0000 0.8204(3) -0.2500 0.0877(18) Uani 1 2 d S T P . .
C37 C 0.1961(9) 0.8243(18) -0.1256(10) 0.125(11) Uani 0.5 1 d . . P E 7
H37A H 0.1881 0.7655 -0.1279 0.150 Uiso 0.5 1 calc R U P E 7
H37B H 0.1853 0.8435 -0.1689 0.150 Uiso 0.5 1 calc R U P E 7
Cl1 Cl 0.14782(11) 0.8712(2) -0.09670(11) 0.0544(6) Uani 0.5 1 d . . P E 7
Cl2 Cl 0.26751(19) 0.8377(5) -0.0867(3) 0.177(4) Uani 0.5 1 d . . P E 7


_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
Ir N3 2.007(4) . ?
Ir C14 2.010(5) . ?
Ir N1 2.010(4) . ?
Ir C5 2.022(4) . ?
Ir N7 2.137(4) . ?
Ir N5 2.137(3) . ?
N1 C1B 1.337(14) . ?
N1 N2 1.363(5) . ?
N1 C1A 1.379(19) . ?
C1A C2A 1.43(3) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.41(4) . ?
C2A H2A 0.9500 . ?
C3A N2 1.40(3) . ?
C3A H3A 0.9500 . ?
C1B C2B 1.39(2) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.34(3) . ?
C2B H2B 0.9500 . ?
C3B N2 1.35(2) . ?
C3B H3B 0.9500 . ?
N2 C4 1.415(6) . ?
C4 C9 1.391(6) . ?
C4 C5 1.398(6) . ?
C5 C6 1.392(6) . ?
C6 C7 1.400(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(7) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
N3 C10 1.338(8) . ?
N3 N4 1.347(7) . ?
C10 C11 1.400(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.319(17) . ?
C11 H11 0.9500 . ?
C12 N4 1.366(11) . ?
C12 H12 0.9500 . ?
N4 C13 1.403(10) . ?
C13 C18 1.393(10) . ?
C13 C14 1.402(9) . ?
C14 C15 1.389(9) . ?
C15 C16 1.414(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.337(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.342(19) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N5 C25A 1.220(10) . ?
N5 C19 1.385(6) . ?
N5 C25B 1.471(10) . ?
C19 C20 1.368(8) . ?
C19 C24 1.391(7) . ?
C19 C25A 1.989(11) . ?
C20 C21 1.393(6) . ?
C20 H20 0.9500 . ?
C21 C35B 1.286(11) . ?
C21 C22 1.416(10) . ?
C21 C35A 1.752(13) . ?
C22 C23 1.327(11) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(8) . ?
C23 H23 0.9500 . ?
C24 N6A 1.170(9) . ?
C24 N6B 1.654(11) . ?
N6A C25A 1.385(11) . ?
N6A C31A 1.483(10) . ?
C25A C26A 1.475(13) . ?
C26A C30A 1.377(13) . ?
C26A N7 1.430(9) . ?
N6B C25B 1.366(10) . ?
N6B C31B 1.473(10) . ?
C25B C26B 1.458(12) . ?
C26B C30B 1.377(13) . ?
C26B N7 1.395(9) . ?
N7 C27 1.321(7) . ?
C27 C28A 1.366(13) . ?
C27 C28B 1.522(14) . ?
C27 H27 0.9500 . ?
C28A C29A 1.387(14) . ?
C28A H28A 0.9500 . ?
C29A C30A 1.394(13) . ?
C29A H29A 0.9500 . ?
C30A H30A 0.9500 . ?
C31A C32A 1.503(12) . ?
C31A H31A 0.9900 . ?
C31A H31B 0.9900 . ?
C32A C33A 1.502(13) . ?
C32A H32A 0.9900 . ?
C32A H32B 0.9900 . ?
C33A C34A 1.507(19) . ?
C33A H33A 0.9900 . ?
C33A H33B 0.9900 . ?
C34A H34A 0.9800 . ?
C34A H34B 0.9800 . ?
C34A H34C 0.9800 . ?
C28B C29B 1.390(16) . ?
C28B H28B 0.9500 . ?
C29B C30B 1.378(14) . ?
C29B H29B 0.9500 . ?
C30B H30B 0.9500 . ?
C31B C32B 1.527(12) . ?
C31B H31C 0.9900 . ?
C31B H31D 0.9900 . ?
C35A O1A 1.203(10) . ?
C35A O2A 1.335(12) . ?
O2A C36A 1.443(11) . ?
C36A H36A 0.9800 . ?
C36A H36B 0.9800 . ?
C36A H36C 0.9800 . ?
C35B O1B 1.230(12) . ?
C35B O2B 1.322(12) . ?
O2B C36B 1.432(12) . ?
C36B H36D 0.9800 . ?
C36B H36E 0.9800 . ?
C36B H36F 0.9800 . ?
P1 F6 1.533(6) . ?
P1 F4 1.574(8) . ?
P1 F3 1.589(6) . ?
P1 F2 1.589(8) . ?
P1 F1 1.605(6) . ?
P1 F5 1.606(7) . ?
P2 F8 1.558(3) 2_554 ?
P2 F8 1.558(3) . ?
P2 F9 1.561(6) . ?
P2 F10 1.563(5) . ?
P2 F7 1.585(3) . ?
P2 F7 1.585(3) 2_554 ?
C37 Cl2 1.62(2) . ?
C37 Cl1 1.76(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?

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
N3 Ir C14 80.2(2) . . ?
N3 Ir N1 171.58(17) . . ?
C14 Ir N1 94.4(2) . . ?
N3 Ir C5 93.25(15) . . ?
C14 Ir C5 88.59(16) . . ?
N1 Ir C5 80.08(16) . . ?
N3 Ir N7 94.3(2) . . ?
C14 Ir N7 172.18(19) . . ?
N1 Ir N7 91.7(2) . . ?
C5 Ir N7 97.36(15) . . ?
N3 Ir N5 95.34(14) . . ?
C14 Ir N5 98.80(15) . . ?
N1 Ir N5 91.86(14) . . ?
C5 Ir N5 169.50(14) . . ?
N7 Ir N5 76.00(15) . . ?
C1B N1 N2 108.8(7) . . ?
N2 N1 C1A 104.1(8) . . ?
C1B N1 Ir 135.2(7) . . ?
N2 N1 Ir 115.0(3) . . ?
C1A N1 Ir 137.0(8) . . ?
N1 C1A C2A 113.2(15) . . ?
N1 C1A H1A 123.4 . . ?
C2A C1A H1A 123.4 . . ?
C3A C2A C1A 101.7(19) . . ?
C3A C2A H2A 129.1 . . ?
C1A C2A H2A 129.1 . . ?
N2 C3A C2A 109(2) . . ?
N2 C3A H3A 125.6 . . ?
C2A C3A H3A 125.6 . . ?
N1 C1B C2B 106.7(12) . . ?
N1 C1B H1B 126.6 . . ?
C2B C1B H1B 126.6 . . ?
C3B C2B C1B 107.8(15) . . ?
C3B C2B H2B 126.1 . . ?
C1B C2B H2B 126.1 . . ?
C2B C3B N2 108.2(16) . . ?
C2B C3B H3B 125.9 . . ?
N2 C3B H3B 125.9 . . ?
C3B N2 N1 107.7(9) . . ?
N1 N2 C3A 110.9(13) . . ?
C3B N2 C4 135.0(10) . . ?
N1 N2 C4 116.3(4) . . ?
C3A N2 C4 130.8(12) . . ?
C9 C4 C5 124.4(4) . . ?
C9 C4 N2 121.4(4) . . ?
C5 C4 N2 114.2(3) . . ?
C6 C5 C4 115.8(4) . . ?
C6 C5 Ir 129.9(3) . . ?
C4 C5 Ir 114.3(3) . . ?
C5 C6 C7 121.0(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 117.5(4) . . ?
C8 C9 H9 121.2 . . ?
C4 C9 H9 121.2 . . ?
C10 N3 N4 107.6(5) . . ?
C10 N3 Ir 136.6(5) . . ?
N4 N3 Ir 115.2(4) . . ?
N3 C10 C11 107.1(10) . . ?
N3 C10 H10 126.4 . . ?
C11 C10 H10 126.4 . . ?
C12 C11 C10 108.6(9) . . ?
C12 C11 H11 125.7 . . ?
C10 C11 H11 125.7 . . ?
C11 C12 N4 107.0(9) . . ?
C11 C12 H12 126.5 . . ?
N4 C12 H12 126.5 . . ?
N3 N4 C12 109.6(8) . . ?
N3 N4 C13 115.8(4) . . ?
C12 N4 C13 134.6(8) . . ?
C18 C13 C14 123.1(10) . . ?
C18 C13 N4 121.8(9) . . ?
C14 C13 N4 115.1(5) . . ?
C15 C14 C13 115.3(6) . . ?
C15 C14 Ir 131.3(5) . . ?
C13 C14 Ir 113.4(5) . . ?
C14 C15 C16 120.5(9) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 121.2(11) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.8(10) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 119.1(11) . . ?
C17 C18 H18 120.5 . . ?
C13 C18 H18 120.5 . . ?
C25A N5 C19 99.3(5) . . ?
C19 N5 C25B 111.5(5) . . ?
C25A N5 Ir 117.0(5) . . ?
C19 N5 Ir 136.7(3) . . ?
C25B N5 Ir 111.7(4) . . ?
C20 C19 N5 130.3(4) . . ?
C20 C19 C24 121.1(5) . . ?
N5 C19 C24 108.6(5) . . ?
C20 C19 C25A 163.6(4) . . ?
N5 C19 C25A 37.2(3) . . ?
C24 C19 C25A 72.3(4) . . ?
C19 C20 C21 116.7(5) . . ?
C19 C20 H20 121.7 . . ?
C21 C20 H20 121.7 . . ?
C35B C21 C20 128.1(7) . . ?
C35B C21 C22 108.6(6) . . ?
C20 C21 C22 120.7(7) . . ?
C20 C21 C35A 113.9(6) . . ?
C22 C21 C35A 124.5(5) . . ?
C23 C22 C21 122.3(5) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 117.0(6) . . ?
C22 C23 H23 121.5 . . ?
C24 C23 H23 121.5 . . ?
N6A C24 C23 127.6(6) . . ?
N6A C24 C19 106.8(5) . . ?
C23 C24 C19 122.3(7) . . ?
C23 C24 N6B 131.2(7) . . ?
C19 C24 N6B 105.0(5) . . ?
C24 N6A C25A 106.5(7) . . ?
C24 N6A C31A 124.1(6) . . ?
C25A N6A C31A 129.3(7) . . ?
N5 C25A N6A 116.0(8) . . ?
N5 C25A C26A 115.7(8) . . ?
N6A C25A C26A 128.2(8) . . ?
N5 C25A C19 43.4(4) . . ?
N6A C25A C19 72.8(5) . . ?
C26A C25A C19 159.0(7) . . ?
C30A C26A N7 116.4(8) . . ?
C30A C26A C25A 127.1(8) . . ?
N7 C26A C25A 115.6(7) . . ?
C25B N6B C31B 128.6(7) . . ?
C25B N6B C24 104.2(6) . . ?
C31B N6B C24 125.9(5) . . ?
N6B C25B C26B 130.6(8) . . ?
N6B C25B N5 108.7(7) . . ?
C26B C25B N5 120.2(7) . . ?
C30B C26B N7 127.1(7) . . ?
C30B C26B C25B 125.6(8) . . ?
N7 C26B C25B 106.8(7) . . ?
C27 N7 C26B 112.3(5) . . ?
C27 N7 C26A 123.9(5) . . ?
C27 N7 Ir 124.2(3) . . ?
C26B N7 Ir 120.0(4) . . ?
C26A N7 Ir 110.1(5) . . ?
N7 C27 C28A 117.5(6) . . ?
N7 C27 C28B 125.2(6) . . ?
N7 C27 H27 121.2 . . ?
C28A C27 H27 121.2 . . ?
C27 C28A C29A 121.3(10) . . ?
C27 C28A H28A 119.3 . . ?
C29A C28A H28A 119.3 . . ?
C28A C29A C30A 119.3(9) . . ?
C28A C29A H29A 120.3 . . ?
C30A C29A H29A 120.3 . . ?
C26A C30A C29A 119.4(8) . . ?
C26A C30A H30A 120.3 . . ?
C29A C30A H30A 120.3 . . ?
N6A C31A C32A 112.9(7) . . ?
N6A C31A H31A 109.0 . . ?
C32A C31A H31A 109.0 . . ?
N6A C31A H31B 109.0 . . ?
C32A C31A H31B 109.0 . . ?
H31A C31A H31B 107.8 . . ?
C33A C32A C31A 114.0(8) . . ?
C33A C32A H32A 108.7 . . ?
C31A C32A H32A 108.7 . . ?
C33A C32A H32B 108.7 . . ?
C31A C32A H32B 108.7 . . ?
H32A C32A H32B 107.6 . . ?
C32A C33A C34A 115.5(9) . . ?
C32A C33A H33A 108.4 . . ?
C34A C33A H33A 108.4 . . ?
C32A C33A H33B 108.4 . . ?
C34A C33A H33B 108.4 . . ?
H33A C33A H33B 107.5 . . ?
C33A C34A H34A 109.5 . . ?
C33A C34A H34B 109.5 . . ?
H34A C34A H34B 109.5 . . ?
C33A C34A H34C 109.5 . . ?
H34A C34A H34C 109.5 . . ?
H34B C34A H34C 109.5 . . ?
C29B C28B C27 115.3(9) . . ?
C29B C28B H28B 122.3 . . ?
C27 C28B H28B 122.3 . . ?
C30B C29B C28B 119.5(10) . . ?
C30B C29B H29B 120.2 . . ?
C28B C29B H29B 120.2 . . ?
C26B C30B C29B 119.1(9) . . ?
C26B C30B H30B 120.4 . . ?
C29B C30B H30B 120.4 . . ?
N6B C31B C32B 112.3(6) . . ?
N6B C31B H31C 109.1 . . ?
C32B C31B H31C 109.1 . . ?
N6B C31B H31D 109.1 . . ?
C32B C31B H31D 109.1 . . ?
H31C C31B H31D 107.9 . . ?
O1A C35A O2A 123.0(10) . . ?
O1A C35A C21 119.7(9) . . ?
O2A C35A C21 117.1(6) . . ?
C35A O2A C36A 117.1(7) . . ?
O2A C36A H36A 109.5 . . ?
O2A C36A H36B 109.5 . . ?
H36A C36A H36B 109.5 . . ?
O2A C36A H36C 109.5 . . ?
H36A C36A H36C 109.5 . . ?
H36B C36A H36C 109.5 . . ?
O1B C35B C21 128.8(9) . . ?
O1B C35B O2B 122.7(9) . . ?
C21 C35B O2B 107.7(8) . . ?
C35B O2B C36B 117.0(8) . . ?
O2B C36B H36D 109.5 . . ?
O2B C36B H36E 109.5 . . ?
H36D C36B H36E 109.5 . . ?
O2B C36B H36F 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?
F6 P1 F4 89.9(4) . . ?
F6 P1 F3 85.8(4) . . ?
F4 P1 F3 81.0(5) . . ?
F6 P1 F2 91.2(4) . . ?
F4 P1 F2 178.3(5) . . ?
F3 P1 F2 97.8(5) . . ?
F6 P1 F1 91.8(4) . . ?
F4 P1 F1 91.7(4) . . ?
F3 P1 F1 172.2(6) . . ?
F2 P1 F1 89.6(4) . . ?
F6 P1 F5 179.0(4) . . ?
F4 P1 F5 90.0(4) . . ?
F3 P1 F5 95.1(4) . . ?
F2 P1 F5 89.0(4) . . ?
F1 P1 F5 87.3(4) . . ?
F8 P2 F8 179.1(4) 2_554 . ?
F8 P2 F9 89.5(2) 2_554 . ?
F8 P2 F9 89.5(2) . . ?
F8 P2 F10 90.5(2) 2_554 . ?
F8 P2 F10 90.5(2) . . ?
F9 P2 F10 180.0 . . ?
F8 P2 F7 92.30(17) 2_554 . ?
F8 P2 F7 87.70(17) . . ?
F9 P2 F7 89.47(15) . . ?
F10 P2 F7 90.53(15) . . ?
F8 P2 F7 87.69(17) 2_554 2_554 ?
F8 P2 F7 92.30(17) . 2_554 ?
F9 P2 F7 89.47(15) . 2_554 ?
F10 P2 F7 90.53(15) . 2_554 ?
F7 P2 F7 178.9(3) . 2_554 ?
Cl2 C37 Cl1 117.5(12) . . ?
Cl2 C37 H37A 107.9 . . ?
Cl1 C37 H37A 107.9 . . ?
Cl2 C37 H37B 107.9 . . ?
Cl1 C37 H37B 107.9 . . ?
H37A C37 H37B 107.2 . . ?

_refine_diff_density_max         1.645
_refine_diff_density_min         -2.134
_refine_diff_density_rms         0.099


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.779 -0.250 0.029 735 176 ' '
2 0.781 0.250 0.531 735 176 ' '
_platon_squeeze_details          
;
Possible disordered solvent residues in what would be
otherwise voids were tried to remove with the option
SQUEEZE by Platon.
In two voids of 735 Å³ each, in the unit cell, 176 electrons
each, were removed.
Total potential solvent accessible void volume per unit cell
is 1468.2 Å³ (17%) with a total electron count/cell of 358.
The total electron count for the potential solvent molecules is:
hexane = 48,
CH2Cl2 = 48.
The structure has Z = 8.
Thus, a half-occupied CH2Cl2 or hexane molecule with Z = 8 would
give 24 x 8 = 192 electrons per void in the unit cell.
With two voids of the same electron count, overall the approximate
 equivalent of a full hexane or CH2Cl2 molecule could be present 
per formula unit.
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'methylene chloride, hexane'
