# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_pbad121109
_database_code_depnum_ccdc_archive 'CCDC 1039710'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H35 Cl Ir N3'
_chemical_formula_sum            'C25 H35 Cl Ir N3'
_chemical_formula_weight         605.21

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'
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                   8.5409(4)
_cell_length_b                   11.3926(5)
_cell_length_c                   13.7162(6)
_cell_angle_alpha                69.6340(10)
_cell_angle_beta                 87.7630(10)
_cell_angle_gamma                71.5300(10)
_cell_volume                     1182.94(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      32.09

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    5.773
_shelx_estimated_absorpt_T_min   0.181
_shelx_estimated_absorpt_T_max   0.478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4167
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23224
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.589
_diffrn_reflns_theta_max         32.137
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8245
_reflns_number_gt                7505
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0148P)²+1.2285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8245
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0455
_refine_ls_wR_factor_gt          0.0434
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8555(3) 0.62510(19) 0.10762(15) 0.0180(4) Uani 1 1 d . . . . .
H1 H 0.8931 0.5475 0.0902 0.022 Uiso 1 1 calc R U . . .
C2 C 0.8223(3) 0.7636(2) 0.18794(16) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.8345 0.8000 0.2387 0.024 Uiso 1 1 calc R U . . .
C3 C 0.7197(3) 0.82919(19) 0.09914(15) 0.0186(4) Uani 1 1 d . . . . .
H3 H 0.6475 0.9180 0.0767 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6585(2) 0.76828(18) -0.04972(14) 0.0159(3) Uani 1 1 d . . . . .
C5 C 0.7265(3) 0.6680(2) -0.10063(18) 0.0307(5) Uani 1 1 d . . . . .
H5A H 0.6551 0.6912 -0.1632 0.046 Uiso 1 1 calc R U . . .
H5B H 0.7306 0.5804 -0.0519 0.046 Uiso 1 1 calc R U . . .
H5C H 0.8385 0.6668 -0.1202 0.046 Uiso 1 1 calc R U . . .
C6 C 0.4456(2) 0.91369(18) -0.17878(14) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.4996(3) 0.98160(19) -0.27390(15) 0.0182(4) Uani 1 1 d . . . . .
C8 C 0.3942(3) 1.0262(2) -0.36385(16) 0.0252(4) Uani 1 1 d . . . . .
H8 H 0.4270 1.0723 -0.4291 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2429(3) 1.0047(2) -0.36026(17) 0.0284(5) Uani 1 1 d . . . . .
H9 H 0.1735 1.0359 -0.4226 0.034 Uiso 1 1 calc R U . . .
C10 C 0.1927(3) 0.9378(2) -0.26601(17) 0.0250(4) Uani 1 1 d . . . . .
H10 H 0.0896 0.9222 -0.2643 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2915(3) 0.8930(2) -0.17338(16) 0.0188(4) Uani 1 1 d . . . . .
C12 C 0.6643(3) 1.0075(2) -0.27655(17) 0.0240(4) Uani 1 1 d . . . . .
H12 H 0.7484 0.9235 -0.2316 0.029 Uiso 1 1 calc R U . . .
C13 C 0.6547(4) 1.1136(3) -0.2301(2) 0.0373(6) Uani 1 1 d . . . . .
H13A H 0.5682 1.1959 -0.2700 0.056 Uiso 1 1 calc R U . . .
H13B H 0.7616 1.1292 -0.2334 0.056 Uiso 1 1 calc R U . . .
H13C H 0.6283 1.0836 -0.1572 0.056 Uiso 1 1 calc R U . . .
C14 C 0.7257(4) 1.0451(3) -0.3858(2) 0.0442(7) Uani 1 1 d . . . . .
H14A H 0.7300 0.9771 -0.4151 0.066 Uiso 1 1 calc R U . . .
H14B H 0.8367 1.0518 -0.3816 0.066 Uiso 1 1 calc R U . . .
H14C H 0.6499 1.1305 -0.4307 0.066 Uiso 1 1 calc R U . . .
C15 C 0.2359(3) 0.8217(2) -0.06966(17) 0.0246(4) Uani 1 1 d . . . . .
H15 H 0.2901 0.8372 -0.0140 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0495(4) 0.8732(4) -0.0640(3) 0.0590(10) Uani 1 1 d . . . . .
H16A H 0.0131 0.9696 -0.0833 0.089 Uiso 1 1 calc R U . . .
H16B H 0.0217 0.8329 0.0072 0.089 Uiso 1 1 calc R U . . .
H16C H -0.0065 0.8503 -0.1123 0.089 Uiso 1 1 calc R U . . .
C17 C 0.2920(5) 0.6732(3) -0.0461(2) 0.0520(9) Uani 1 1 d . . . . .
H17A H 0.2454 0.6553 -0.1016 0.078 Uiso 1 1 calc R U . . .
H17B H 0.2534 0.6295 0.0208 0.078 Uiso 1 1 calc R U . . .
H17C H 0.4131 0.6390 -0.0425 0.078 Uiso 1 1 calc R U . . .
C18 C 1.1714(3) 0.6158(2) 0.34784(17) 0.0225(4) Uani 1 1 d . . . . .
H18 H 1.0582 0.6691 0.3379 0.027 Uiso 1 1 calc R U . . .
C19 C 1.2521(3) 0.5954(2) 0.25996(17) 0.0236(4) Uani 1 1 d . . . . .
H19 H 1.1904 0.6385 0.1939 0.028 Uiso 1 1 calc R U . . .
C20 C 1.4307(3) 0.5093(3) 0.2643(2) 0.0317(5) Uani 1 1 d . . . . .
H20A H 1.5054 0.5534 0.2786 0.038 Uiso 1 1 calc R U . . .
H20B H 1.4531 0.5002 0.1954 0.038 Uiso 1 1 calc R U . . .
C21 C 1.4689(3) 0.3708(3) 0.3486(2) 0.0326(5) Uani 1 1 d . . . . .
H21A H 1.5539 0.3059 0.3253 0.039 Uiso 1 1 calc R U . . .
H21B H 1.5148 0.3709 0.4137 0.039 Uiso 1 1 calc R U . . .
C22 C 1.3156(3) 0.3284(2) 0.37070(18) 0.0265(5) Uani 1 1 d . . . . .
H22 H 1.2877 0.2853 0.3291 0.032 Uiso 1 1 calc R U . . .
C23 C 1.2129(3) 0.3497(2) 0.44965(17) 0.0271(5) Uani 1 1 d . . . . .
H23 H 1.1219 0.3169 0.4602 0.033 Uiso 1 1 calc R U . . .
C24 C 1.2379(3) 0.4216(3) 0.51906(18) 0.0314(5) Uani 1 1 d . . . . .
H24A H 1.3379 0.3658 0.5674 0.038 Uiso 1 1 calc R U . . .
H24B H 1.1419 0.4346 0.5616 0.038 Uiso 1 1 calc R U . . .
C25 C 1.2574(3) 0.5563(3) 0.45752(19) 0.0297(5) Uani 1 1 d . . . . .
H25A H 1.2103 0.6178 0.4954 0.036 Uiso 1 1 calc R U . . .
H25B H 1.3767 0.5460 0.4528 0.036 Uiso 1 1 calc R U . . .
N1 N 0.9065(2) 0.63538(16) 0.19307(13) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.7416(2) 0.74069(16) 0.04797(12) 0.0153(3) Uani 1 1 d . . . . .
N3 N 0.5399(2) 0.87546(16) -0.08273(12) 0.0152(3) Uani 1 1 d . . . . .
Cl1 Cl 0.95784(8) 0.33525(6) 0.29214(5) 0.03161(12) Uani 1 1 d . . . . .
Ir1 Ir 1.09046(2) 0.48388(2) 0.30278(2) 0.01702(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.321(2) . ?
C1 N2 1.360(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.358(3) . ?
C2 N1 1.387(3) . ?
C2 H2 0.9500 . ?
C3 N2 1.381(2) . ?
C3 H3 0.9500 . ?
C4 N3 1.261(2) . ?
C4 N2 1.427(2) . ?
C4 C5 1.494(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.403(3) . ?
C6 C7 1.411(3) . ?
C6 N3 1.427(2) . ?
C7 C8 1.397(3) . ?
C7 C12 1.523(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(3) . ?
C10 H10 0.9500 . ?
C11 C15 1.515(3) . ?
C12 C14 1.530(3) . ?
C12 C13 1.531(4) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.522(4) . ?
C15 C17 1.522(4) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.418(3) . ?
C18 C25 1.524(3) . ?
C18 Ir1 2.111(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.520(3) . ?
C19 Ir1 2.096(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.539(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.519(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.405(4) . ?
C22 Ir1 2.130(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.514(3) . ?
C23 Ir1 2.121(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.532(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N1 Ir1 2.0903(16) . ?
Cl1 Ir1 2.3605(6) . ?

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 C1 N2 110.79(17) . . ?
N1 C1 H1 124.6 . . ?
N2 C1 H1 124.6 . . ?
C3 C2 N1 109.58(17) . . ?
C3 C2 H2 125.2 . . ?
N1 C2 H2 125.2 . . ?
C2 C3 N2 106.14(17) . . ?
C2 C3 H3 126.9 . . ?
N2 C3 H3 126.9 . . ?
N3 C4 N2 115.70(17) . . ?
N3 C4 C5 128.60(18) . . ?
N2 C4 C5 115.68(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 121.95(17) . . ?
C11 C6 N3 117.46(17) . . ?
C7 C6 N3 120.29(17) . . ?
C8 C7 C6 117.23(19) . . ?
C8 C7 C12 122.07(19) . . ?
C6 C7 C12 120.69(17) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 118.23(19) . . ?
C10 C11 C15 121.13(19) . . ?
C6 C11 C15 120.63(17) . . ?
C7 C12 C14 113.2(2) . . ?
C7 C12 C13 111.0(2) . . ?
C14 C12 C13 110.2(2) . . ?
C7 C12 H12 107.4 . . ?
C14 C12 H12 107.4 . . ?
C13 C12 H12 107.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 C16 112.7(2) . . ?
C11 C15 C17 111.1(2) . . ?
C16 C15 C17 109.8(3) . . ?
C11 C15 H15 107.7 . . ?
C16 C15 H15 107.7 . . ?
C17 C15 H15 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C25 123.2(2) . . ?
C19 C18 Ir1 69.74(12) . . ?
C25 C18 Ir1 114.22(16) . . ?
C19 C18 H18 118.4 . . ?
C25 C18 H18 118.4 . . ?
Ir1 C18 H18 86.1 . . ?
C18 C19 C20 124.4(2) . . ?
C18 C19 Ir1 70.87(13) . . ?
C20 C19 Ir1 112.18(16) . . ?
C18 C19 H19 117.8 . . ?
C20 C19 H19 117.8 . . ?
Ir1 C19 H19 86.9 . . ?
C19 C20 C21 112.5(2) . . ?
C19 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 111.96(19) . . ?
C22 C21 H21A 109.2 . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C21 123.3(2) . . ?
C23 C22 Ir1 70.33(12) . . ?
C21 C22 Ir1 113.82(16) . . ?
C23 C22 H22 118.4 . . ?
C21 C22 H22 118.4 . . ?
Ir1 C22 H22 85.9 . . ?
C22 C23 C24 124.2(2) . . ?
C22 C23 Ir1 71.05(12) . . ?
C24 C23 Ir1 111.58(15) . . ?
C22 C23 H23 117.9 . . ?
C24 C23 H23 117.9 . . ?
Ir1 C23 H23 87.4 . . ?
C23 C24 C25 112.94(19) . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C18 C25 C24 112.07(19) . . ?
C18 C25 H25A 109.2 . . ?
C24 C25 H25A 109.2 . . ?
C18 C25 H25B 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C1 N1 C2 106.12(16) . . ?
C1 N1 Ir1 123.43(13) . . ?
C2 N1 Ir1 130.34(13) . . ?
C1 N2 C3 107.36(15) . . ?
C1 N2 C4 127.33(16) . . ?
C3 N2 C4 125.30(16) . . ?
C4 N3 C6 121.16(17) . . ?
N1 Ir1 C19 90.42(8) . . ?
N1 Ir1 C18 93.71(7) . . ?
C19 Ir1 C18 39.39(9) . . ?
N1 Ir1 C23 159.58(9) . . ?
C19 Ir1 C23 98.30(9) . . ?
C18 Ir1 C23 81.81(9) . . ?
N1 Ir1 C22 161.81(8) . . ?
C19 Ir1 C22 81.83(9) . . ?
C18 Ir1 C22 90.68(9) . . ?
C23 Ir1 C22 38.62(10) . . ?
N1 Ir1 Cl1 87.98(5) . . ?
C19 Ir1 Cl1 156.19(7) . . ?
C18 Ir1 Cl1 164.41(7) . . ?
C23 Ir1 Cl1 91.22(7) . . ?
C22 Ir1 Cl1 92.51(7) . . ?

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 C2 C3 N2 -0.5(3) . . . . ?
C11 C6 C7 C8 -1.0(3) . . . . ?
N3 C6 C7 C8 -174.55(18) . . . . ?
C11 C6 C7 C12 177.45(19) . . . . ?
N3 C6 C7 C12 3.9(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C12 C7 C8 C9 -178.5(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C6 -2.0(3) . . . . ?
C9 C10 C11 C15 178.9(2) . . . . ?
C7 C6 C11 C10 2.1(3) . . . . ?
N3 C6 C11 C10 175.77(19) . . . . ?
C7 C6 C11 C15 -178.92(19) . . . . ?
N3 C6 C11 C15 -5.2(3) . . . . ?
C8 C7 C12 C14 -18.2(3) . . . . ?
C6 C7 C12 C14 163.4(2) . . . . ?
C8 C7 C12 C13 106.3(2) . . . . ?
C6 C7 C12 C13 -72.1(3) . . . . ?
C10 C11 C15 C16 -34.3(3) . . . . ?
C6 C11 C15 C16 146.7(3) . . . . ?
C10 C11 C15 C17 89.4(3) . . . . ?
C6 C11 C15 C17 -89.6(3) . . . . ?
C25 C18 C19 C20 2.0(3) . . . . ?
Ir1 C18 C19 C20 -104.3(2) . . . . ?
C25 C18 C19 Ir1 106.3(2) . . . . ?
C18 C19 C20 C21 50.5(3) . . . . ?
Ir1 C19 C20 C21 -30.9(2) . . . . ?
C19 C20 C21 C22 27.2(3) . . . . ?
C20 C21 C22 C23 -92.7(3) . . . . ?
C20 C21 C22 Ir1 -11.4(3) . . . . ?
C21 C22 C23 C24 2.5(3) . . . . ?
Ir1 C22 C23 C24 -103.7(2) . . . . ?
C21 C22 C23 Ir1 106.2(2) . . . . ?
C22 C23 C24 C25 51.1(3) . . . . ?
Ir1 C23 C24 C25 -30.1(3) . . . . ?
C19 C18 C25 C24 -91.6(3) . . . . ?
Ir1 C18 C25 C24 -10.7(3) . . . . ?
C23 C24 C25 C18 26.6(3) . . . . ?
N2 C1 N1 C2 -0.3(2) . . . . ?
N2 C1 N1 Ir1 -176.73(13) . . . . ?
C3 C2 N1 C1 0.5(3) . . . . ?
C3 C2 N1 Ir1 176.60(15) . . . . ?
N1 C1 N2 C3 0.0(2) . . . . ?
N1 C1 N2 C4 179.88(19) . . . . ?
C2 C3 N2 C1 0.3(2) . . . . ?
C2 C3 N2 C4 -179.58(19) . . . . ?
N3 C4 N2 C1 169.5(2) . . . . ?
C5 C4 N2 C1 -12.1(3) . . . . ?
N3 C4 N2 C3 -10.6(3) . . . . ?
C5 C4 N2 C3 167.8(2) . . . . ?
N2 C4 N3 C6 -179.23(17) . . . . ?
C5 C4 N3 C6 2.6(3) . . . . ?
C11 C6 N3 C4 100.5(2) . . . . ?
C7 C6 N3 C4 -85.7(2) . . . . ?

_refine_diff_density_max         2.374
_refine_diff_density_min         -1.294
_refine_diff_density_rms         0.110

_shelxl_version_number           2013-4

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

data_pbfh141126
_database_code_depnum_ccdc_archive 'CCDC 1039711'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H36 Cl Ir N3, B F4'
_chemical_formula_sum            'C25 H36 B Cl F4 Ir N3'
_chemical_formula_weight         693.03

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   22.1698(9)
_cell_length_b                   20.5501(8)
_cell_length_c                   14.5843(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.9360(10)
_cell_angle_gamma                90
_cell_volume                     6205.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      34.06

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             2736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.429
_shelx_estimated_absorpt_T_min   0.306
_shelx_estimated_absorpt_T_max   0.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5676
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50764
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.396
_diffrn_reflns_theta_max         34.081
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12686
_reflns_number_gt                10025
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0324P)²+23.5269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12686
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14062(12) 0.04151(12) 0.67948(18) 0.0218(4) Uani 1 1 d . . . . .
C2 C 0.06613(14) -0.01540(14) 0.7172(2) 0.0287(5) Uani 1 1 d . . . . .
H2 H 0.0348 -0.0478 0.7136 0.034 Uiso 1 1 calc R U . . .
C3 C 0.08509(14) 0.03306(14) 0.7833(2) 0.0278(5) Uani 1 1 d . . . . .
H3 H 0.0698 0.0419 0.8352 0.033 Uiso 1 1 calc R U . . .
C4 C 0.16325(14) 0.12581(13) 0.79681(19) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.1495(2) 0.15708(17) 0.8791(3) 0.0423(8) Uani 1 1 d . . . . .
H5A H 0.1754 0.1968 0.8992 0.063 Uiso 1 1 calc R U . . .
H5B H 0.1605 0.1269 0.9348 0.063 Uiso 1 1 calc R U . . .
H5C H 0.1035 0.1681 0.8577 0.063 Uiso 1 1 calc R U . . .
C6 C 0.22826(13) 0.21173(13) 0.77619(19) 0.0241(5) Uani 1 1 d . . . . .
C7 C 0.19002(14) 0.26456(13) 0.7272(2) 0.0263(5) Uani 1 1 d . . . . .
C8 C 0.21824(16) 0.32599(14) 0.7451(2) 0.0327(6) Uani 1 1 d . . . . .
H8 H 0.1938 0.3627 0.7127 0.039 Uiso 1 1 calc R U . . .
C9 C 0.28100(17) 0.33498(16) 0.8089(2) 0.0367(7) Uani 1 1 d . . . . .
H9 H 0.2991 0.3774 0.8193 0.044 Uiso 1 1 calc R U . . .
C10 C 0.31743(16) 0.28274(17) 0.8574(3) 0.0390(7) Uani 1 1 d . . . . .
H10 H 0.3609 0.2894 0.8995 0.047 Uiso 1 1 calc R U . . .
C11 C 0.29214(14) 0.2220(2) 0.8458(2) 0.0378(7) Uani 1 1 d . . . . .
C12 C 0.12013(14) 0.25813(15) 0.6582(2) 0.0323(6) Uani 1 1 d . . . . .
H12 H 0.1094 0.2107 0.6495 0.039 Uiso 1 1 calc R U . . .
C13 C 0.0741(2) 0.2900(3) 0.7013(4) 0.0594(11) Uani 1 1 d . . . . .
H13A H 0.0825 0.3369 0.7081 0.089 Uiso 1 1 calc R U . . .
H13B H 0.0807 0.2711 0.7659 0.089 Uiso 1 1 calc R U . . .
H13C H 0.0294 0.2825 0.6575 0.089 Uiso 1 1 calc R U . . .
C14 C 0.1088(2) 0.2870(2) 0.5573(3) 0.0520(10) Uani 1 1 d . . . . .
H14A H 0.1171 0.3339 0.5635 0.078 Uiso 1 1 calc R U . . .
H14B H 0.0640 0.2792 0.5143 0.078 Uiso 1 1 calc R U . . .
H14C H 0.1381 0.2664 0.5291 0.078 Uiso 1 1 calc R U . . .
C15 C 0.3303(2) 0.16310(18) 0.9037(3) 0.0528(11) Uani 1 1 d . . . . .
H15 H 0.3061 0.1224 0.8754 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3352(3) 0.1691(2) 1.0102(4) 0.0760(17) Uani 1 1 d . . . . .
H16A H 0.3584 0.1315 1.0475 0.114 Uiso 1 1 calc R U . . .
H16B H 0.2917 0.1708 1.0130 0.114 Uiso 1 1 calc R U . . .
H16C H 0.3586 0.2091 1.0386 0.114 Uiso 1 1 calc R U . . .
C17 C 0.3982(3) 0.1585(3) 0.8994(5) 0.091(2) Uani 1 1 d . . . . .
H17A H 0.4226 0.1978 0.9280 0.137 Uiso 1 1 calc R U . . .
H17B H 0.3950 0.1544 0.8309 0.137 Uiso 1 1 calc R U . . .
H17C H 0.4204 0.1203 0.9365 0.137 Uiso 1 1 calc R U . . .
C18 C 0.25310(18) 0.16140(16) 0.5713(3) 0.0375(7) Uani 1 1 d . . . . .
H18 H 0.2410 0.1933 0.6087 0.045 Uiso 1 1 calc R U . . .
C19 C 0.3006(2) 0.1186(2) 0.6215(4) 0.0529(10) Uani 1 1 d . . . . .
H19 H 0.3195 0.1219 0.6910 0.063 Uiso 1 1 calc R U . . .
C20 C 0.3244(3) 0.0654(3) 0.5693(6) 0.097(2) Uani 1 1 d . . . . .
H20A H 0.3248 0.0835 0.5066 0.116 Uiso 1 1 calc R U . . .
H20B H 0.3696 0.0548 0.6102 0.116 Uiso 1 1 calc R U . . .
C21 C 0.2867(3) 0.0037(3) 0.5474(4) 0.0655(13) Uani 1 1 d . . . . .
H21A H 0.3098 -0.0289 0.5977 0.079 Uiso 1 1 calc R U . . .
H21B H 0.2858 -0.0128 0.4832 0.079 Uiso 1 1 calc R U . . .
C22 C 0.2185(2) 0.00859(17) 0.5444(3) 0.0435(8) Uani 1 1 d . . . . .
H22 H 0.2059 -0.0203 0.5852 0.052 Uiso 1 1 calc R U . . .
C23 C 0.17259(18) 0.05132(16) 0.4875(2) 0.0377(7) Uani 1 1 d . . . . .
H23 H 0.1311 0.0512 0.4930 0.045 Uiso 1 1 calc R U . . .
C24 C 0.1851(3) 0.0988(2) 0.4165(3) 0.0518(10) Uani 1 1 d . . . . .
H24A H 0.1433 0.1095 0.3645 0.062 Uiso 1 1 calc R U . . .
H24B H 0.2122 0.0767 0.3846 0.062 Uiso 1 1 calc R U . . .
C25 C 0.2183(3) 0.1622(2) 0.4616(3) 0.0584(12) Uani 1 1 d . . . . .
H25A H 0.2498 0.1737 0.4302 0.070 Uiso 1 1 calc R U . . .
H25B H 0.1853 0.1970 0.4454 0.070 Uiso 1 1 calc R U . . .
N1 N 0.10116(11) -0.00934(12) 0.65480(18) 0.0250(4) Uani 1 1 d . . . . .
N2 N 0.13171(11) 0.06769(11) 0.76020(16) 0.0229(4) Uani 1 1 d . . . . .
N3 N 0.20125(11) 0.14674(11) 0.75383(16) 0.0232(4) Uani 1 1 d . . . . .
B1 B 0.48367(17) 0.37365(19) 1.0214(3) 0.0360(7) Uani 1 1 d . . . . .
F1 F 0.47020(14) 0.31057(14) 0.9934(3) 0.0879(11) Uani 1 1 d . . . . .
F2 F 0.42508(11) 0.40804(11) 1.00042(18) 0.0506(6) Uani 1 1 d . . . . .
F3 F 0.51871(14) 0.40526(18) 0.9732(2) 0.0785(10) Uani 1 1 d . . . . .
F4 F 0.51634(13) 0.37530(14) 1.12068(18) 0.0643(7) Uani 1 1 d . . . . .
Cl1 Cl 0.28097(4) 0.01476(4) 0.77083(6) 0.03405(15) Uani 1 1 d . . . . .
Ir1 Ir 0.20715(2) 0.08545(2) 0.63994(2) 0.02277(3) Uani 1 1 d . . . . .
H1N H 0.0969(19) -0.032(2) 0.613(3) 0.036(11) Uiso 1 1 d . . . . .
H1 H 0.157(2) 0.122(2) 0.583(3) 0.060(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.327(3) . ?
C1 N2 1.371(3) . ?
C1 Ir1 1.983(2) . ?
C2 C3 1.345(4) . ?
C2 N1 1.397(4) . ?
C2 H2 0.9500 . ?
C3 N2 1.392(3) . ?
C3 H3 0.9500 . ?
C4 N3 1.290(3) . ?
C4 N2 1.391(3) . ?
C4 C5 1.486(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.405(4) . ?
C6 C11 1.433(4) . ?
C6 N3 1.452(3) . ?
C7 C8 1.392(4) . ?
C7 C12 1.522(4) . ?
C8 C9 1.382(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.354(5) . ?
C10 H10 0.9500 . ?
C11 C15 1.544(5) . ?
C12 C14 1.522(5) . ?
C12 C13 1.524(5) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.523(7) . ?
C15 C17 1.531(7) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.367(6) . ?
C18 C25 1.508(5) . ?
C18 Ir1 2.281(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.529(7) . ?
C19 Ir1 2.287(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.489(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.501(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.375(6) . ?
C22 Ir1 2.180(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.519(5) . ?
C23 Ir1 2.191(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.525(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N1 H1N 0.75(4) . ?
N3 Ir1 2.125(2) . ?
B1 F1 1.360(5) . ?
B1 F4 1.368(4) . ?
B1 F3 1.383(5) . ?
B1 F2 1.413(4) . ?
Cl1 Ir1 2.4901(8) . ?
Ir1 H1 1.34(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 105.0(2) . . ?
N1 C1 Ir1 140.0(2) . . ?
N2 C1 Ir1 114.92(18) . . ?
C3 C2 N1 107.3(2) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C2 C3 N2 105.9(2) . . ?
C2 C3 H3 127.1 . . ?
N2 C3 H3 127.1 . . ?
N3 C4 N2 115.2(2) . . ?
N3 C4 C5 127.3(3) . . ?
N2 C4 C5 117.5(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 120.7(3) . . ?
C7 C6 N3 118.1(2) . . ?
C11 C6 N3 121.2(3) . . ?
C8 C7 C6 117.2(3) . . ?
C8 C7 C12 119.1(3) . . ?
C6 C7 C12 123.8(2) . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 119.0(3) . . ?
C10 C11 C15 122.2(3) . . ?
C6 C11 C15 118.8(3) . . ?
C7 C12 C14 112.5(3) . . ?
C7 C12 C13 111.3(3) . . ?
C14 C12 C13 109.1(3) . . ?
C7 C12 H12 107.9 . . ?
C14 C12 H12 107.9 . . ?
C13 C12 H12 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C17 109.5(4) . . ?
C16 C15 C11 108.6(3) . . ?
C17 C15 C11 112.4(4) . . ?
C16 C15 H15 108.7 . . ?
C17 C15 H15 108.7 . . ?
C11 C15 H15 108.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C25 125.4(4) . . ?
C19 C18 Ir1 72.80(19) . . ?
C25 C18 Ir1 109.5(2) . . ?
C19 C18 H18 117.3 . . ?
C25 C18 H18 117.3 . . ?
Ir1 C18 H18 87.7 . . ?
C18 C19 C20 122.0(5) . . ?
C18 C19 Ir1 72.36(19) . . ?
C20 C19 Ir1 109.5(3) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
Ir1 C19 H19 88.2 . . ?
C21 C20 C19 116.7(3) . . ?
C21 C20 H20A 108.1 . . ?
C19 C20 H20A 108.1 . . ?
C21 C20 H20B 108.1 . . ?
C19 C20 H20B 108.1 . . ?
H20A C20 H20B 107.3 . . ?
C20 C21 C22 115.5(4) . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21B 108.4 . . ?
C22 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C23 C22 C21 125.5(4) . . ?
C23 C22 Ir1 72.13(19) . . ?
C21 C22 Ir1 112.0(3) . . ?
C23 C22 H22 117.2 . . ?
C21 C22 H22 117.2 . . ?
Ir1 C22 H22 85.7 . . ?
C22 C23 C24 123.0(4) . . ?
C22 C23 Ir1 71.20(19) . . ?
C24 C23 Ir1 113.8(2) . . ?
C22 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
Ir1 C23 H23 85.1 . . ?
C23 C24 C25 115.6(3) . . ?
C23 C24 H24A 108.4 . . ?
C25 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
C25 C24 H24B 108.4 . . ?
H24A C24 H24B 107.4 . . ?
C18 C25 C24 115.7(3) . . ?
C18 C25 H25A 108.4 . . ?
C24 C25 H25A 108.4 . . ?
C18 C25 H25B 108.4 . . ?
C24 C25 H25B 108.4 . . ?
H25A C25 H25B 107.4 . . ?
C1 N1 C2 111.1(2) . . ?
C1 N1 H1N 126(3) . . ?
C2 N1 H1N 123(3) . . ?
C1 N2 C4 117.4(2) . . ?
C1 N2 C3 110.8(2) . . ?
C4 N2 C3 131.4(2) . . ?
C4 N3 C6 119.1(2) . . ?
C4 N3 Ir1 114.53(17) . . ?
C6 N3 Ir1 125.79(17) . . ?
F1 B1 F4 108.5(3) . . ?
F1 B1 F3 113.4(4) . . ?
F4 B1 F3 110.2(3) . . ?
F1 B1 F2 109.0(3) . . ?
F4 B1 F2 108.4(3) . . ?
F3 B1 F2 107.2(3) . . ?
C1 Ir1 N3 77.45(9) . . ?
C1 Ir1 C22 97.10(12) . . ?
N3 Ir1 C22 169.26(12) . . ?
C1 Ir1 C23 97.03(11) . . ?
N3 Ir1 C23 152.31(12) . . ?
C22 Ir1 C23 36.66(15) . . ?
C1 Ir1 C18 159.14(13) . . ?
N3 Ir1 C18 95.69(10) . . ?
C22 Ir1 C18 92.51(13) . . ?
C23 Ir1 C18 79.81(12) . . ?
C1 Ir1 C19 165.78(14) . . ?
N3 Ir1 C19 103.11(14) . . ?
C22 Ir1 C19 79.88(16) . . ?
C23 Ir1 C19 88.81(16) . . ?
C18 Ir1 C19 34.84(15) . . ?
C1 Ir1 Cl1 82.23(8) . . ?
N3 Ir1 Cl1 87.35(6) . . ?
C22 Ir1 Cl1 82.71(11) . . ?
C23 Ir1 Cl1 119.12(10) . . ?
C18 Ir1 Cl1 117.47(10) . . ?
C19 Ir1 Cl1 83.61(12) . . ?
C1 Ir1 H1 84(2) . . ?
N3 Ir1 H1 84(2) . . ?
C22 Ir1 H1 105(2) . . ?
C23 Ir1 H1 69(2) . . ?
C18 Ir1 H1 75(2) . . ?
C19 Ir1 H1 110(2) . . ?
Cl1 Ir1 H1 165(2) . . ?

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 C2 C3 N2 -0.3(3) . . . . ?
C11 C6 C7 C8 3.6(4) . . . . ?
N3 C6 C7 C8 -176.1(3) . . . . ?
C11 C6 C7 C12 -175.3(3) . . . . ?
N3 C6 C7 C12 5.0(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C12 C7 C8 C9 178.4(3) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 C11 -1.8(5) . . . . ?
C9 C10 C11 C6 4.8(5) . . . . ?
C9 C10 C11 C15 -176.3(4) . . . . ?
C7 C6 C11 C10 -5.8(5) . . . . ?
N3 C6 C11 C10 173.9(3) . . . . ?
C7 C6 C11 C15 175.2(3) . . . . ?
N3 C6 C11 C15 -5.0(4) . . . . ?
C8 C7 C12 C14 56.1(4) . . . . ?
C6 C7 C12 C14 -125.0(3) . . . . ?
C8 C7 C12 C13 -66.8(4) . . . . ?
C6 C7 C12 C13 112.1(4) . . . . ?
C10 C11 C15 C16 72.0(5) . . . . ?
C6 C11 C15 C16 -109.1(4) . . . . ?
C10 C11 C15 C17 -49.4(5) . . . . ?
C6 C11 C15 C17 129.5(4) . . . . ?
C25 C18 C19 C20 0.4(5) . . . . ?
Ir1 C18 C19 C20 102.4(3) . . . . ?
C25 C18 C19 Ir1 -102.0(3) . . . . ?
C18 C19 C20 C21 -84.7(6) . . . . ?
Ir1 C19 C20 C21 -3.8(7) . . . . ?
C19 C20 C21 C22 21.6(8) . . . . ?
C20 C21 C22 C23 54.3(6) . . . . ?
C20 C21 C22 Ir1 -28.9(6) . . . . ?
C21 C22 C23 C24 2.0(5) . . . . ?
Ir1 C22 C23 C24 106.7(3) . . . . ?
C21 C22 C23 Ir1 -104.7(4) . . . . ?
C22 C23 C24 C25 -83.3(5) . . . . ?
Ir1 C23 C24 C25 -1.0(5) . . . . ?
C19 C18 C25 C24 56.1(6) . . . . ?
Ir1 C18 C25 C24 -26.3(5) . . . . ?
C23 C24 C25 C18 18.9(6) . . . . ?
N2 C1 N1 C2 1.2(3) . . . . ?
Ir1 C1 N1 C2 177.8(2) . . . . ?
C3 C2 N1 C1 -0.6(3) . . . . ?
N1 C1 N2 C4 -174.4(2) . . . . ?
Ir1 C1 N2 C4 8.1(3) . . . . ?
N1 C1 N2 C3 -1.4(3) . . . . ?
Ir1 C1 N2 C3 -178.95(19) . . . . ?
N3 C4 N2 C1 -4.3(4) . . . . ?
C5 C4 N2 C1 175.1(3) . . . . ?
N3 C4 N2 C3 -175.5(3) . . . . ?
C5 C4 N2 C3 3.9(5) . . . . ?
C2 C3 N2 C1 1.0(3) . . . . ?
C2 C3 N2 C4 172.7(3) . . . . ?
N2 C4 N3 C6 170.3(2) . . . . ?
C5 C4 N3 C6 -9.0(5) . . . . ?
N2 C4 N3 Ir1 -1.3(3) . . . . ?
C5 C4 N3 Ir1 179.4(3) . . . . ?
C7 C6 N3 C4 -82.2(3) . . . . ?
C11 C6 N3 C4 98.1(3) . . . . ?
C7 C6 N3 Ir1 88.4(3) . . . . ?
C11 C6 N3 Ir1 -91.3(3) . . . . ?

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
N1 H1N F2 0.75(4) 1.98(4) 2.721(3) 173(4) 4_546

_refine_diff_density_max         3.074
_refine_diff_density_min         -2.275
_refine_diff_density_rms         0.135

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
1 0.500 0.000 0.017 642.1 174.1
2 1.000 0.500 0.000 642.1 174.1
_platon_squeeze_details          
;
 The residual electron density was assigned to one molecule of the
 diethyl ether solvent [348/8 = 44 e per asymmetric unit; one molecule
 of C4H10O would give 42e].
;

_shelxl_version_number           2013-4

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

data_pbmw140303
_database_code_depnum_ccdc_archive 'CCDC 1039712'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H47 Cl2 Ir2 N3'
_chemical_formula_sum            'C33 H47 Cl2 Ir2 N3'
_chemical_formula_weight         941.03

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

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

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

_cell_length_a                   8.7044(3)
_cell_length_b                   21.9069(8)
_cell_length_c                   19.1631(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.4070(10)
_cell_angle_gamma                90
_cell_volume                     3300.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      31.95

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    8.243
_shelx_estimated_absorpt_T_min   0.160
_shelx_estimated_absorpt_T_max   0.289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5261
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34723
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.499
_diffrn_reflns_theta_max         31.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11428
_reflns_number_gt                9433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0174P)²+17.0033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11428
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4779(4) 0.09243(16) 0.8927(2) 0.0154(6) Uani 1 1 d . . . . .
C2 C 0.3400(5) 0.05597(18) 0.9622(2) 0.0199(7) Uani 1 1 d . . . . .
H2 H 0.2975 0.0515 1.0001 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3136(5) 0.01875(18) 0.9024(2) 0.0210(7) Uani 1 1 d . . . . .
H3 H 0.2472 -0.0175 0.8908 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5003(4) 0.15515(17) 0.9989(2) 0.0159(6) Uani 1 1 d . . . . .
C5 C 0.4606(6) 0.16493(19) 1.0659(2) 0.0251(8) Uani 1 1 d . . . . .
H5A H 0.5144 0.2028 1.0924 0.038 Uiso 1 1 calc R U . . .
H5B H 0.5040 0.1305 1.1018 0.038 Uiso 1 1 calc R U . . .
H5C H 0.3371 0.1679 1.0479 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6563(4) 0.24785(16) 1.01740(19) 0.0152(6) Uani 1 1 d . . . . .
C7 C 0.5603(5) 0.30162(18) 0.9987(2) 0.0195(7) Uani 1 1 d . . . . .
C8 C 0.6396(5) 0.35496(19) 1.0367(3) 0.0266(8) Uani 1 1 d . . . . .
H8 H 0.5781 0.3923 1.0238 0.032 Uiso 1 1 calc R U . . .
C9 C 0.8063(6) 0.3548(2) 1.0928(3) 0.0291(9) Uani 1 1 d . . . . .
H9 H 0.8580 0.3917 1.1179 0.035 Uiso 1 1 calc R U . . .
C10 C 0.8966(5) 0.3009(2) 1.1121(2) 0.0249(8) Uani 1 1 d . . . . .
H10 H 1.0100 0.3010 1.1514 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8249(5) 0.24610(18) 1.0751(2) 0.0195(7) Uani 1 1 d . . . . .
C12 C 0.3736(5) 0.30393(19) 0.9422(2) 0.0228(7) Uani 1 1 d . . . . .
H12 H 0.3401 0.2625 0.9185 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3366(6) 0.3498(3) 0.8768(3) 0.0392(11) Uani 1 1 d . . . . .
H13A H 0.3621 0.3912 0.8983 0.059 Uiso 1 1 calc R U . . .
H13B H 0.2164 0.3472 0.8402 0.059 Uiso 1 1 calc R U . . .
H13C H 0.4077 0.3405 0.8500 0.059 Uiso 1 1 calc R U . . .
C14 C 0.2635(5) 0.3189(2) 0.9844(3) 0.0312(9) Uani 1 1 d . . . . .
H14A H 0.2873 0.2896 1.0264 0.047 Uiso 1 1 calc R U . . .
H14B H 0.1431 0.3165 0.9481 0.047 Uiso 1 1 calc R U . . .
H14C H 0.2897 0.3603 1.0058 0.047 Uiso 1 1 calc R U . . .
C15 C 0.9278(5) 0.1873(2) 1.0989(2) 0.0247(8) Uani 1 1 d . . . . .
H15 H 0.8723 0.1566 1.0569 0.030 Uiso 1 1 calc R U . . .
C16 C 0.9316(7) 0.1612(3) 1.1733(3) 0.0436(13) Uani 1 1 d . . . . .
H16A H 0.9853 0.1906 1.2153 0.065 Uiso 1 1 calc R U . . .
H16B H 0.9969 0.1231 1.1862 0.065 Uiso 1 1 calc R U . . .
H16C H 0.8151 0.1530 1.1663 0.065 Uiso 1 1 calc R U . . .
C17 C 1.1098(6) 0.1962(3) 1.1095(4) 0.0486(15) Uani 1 1 d . . . . .
H17A H 1.1092 0.2151 1.0630 0.073 Uiso 1 1 calc R U . . .
H17B H 1.1671 0.1566 1.1183 0.073 Uiso 1 1 calc R U . . .
H17C H 1.1704 0.2228 1.1541 0.073 Uiso 1 1 calc R U . . .
C18 C 0.5822(6) 0.1416(2) 0.7590(2) 0.0269(9) Uani 1 1 d . . . . .
H18 H 0.4759 0.1243 0.7510 0.032 Uiso 1 1 calc R U . . .
C19 C 0.7292(5) 0.11260(19) 0.8108(2) 0.0240(8) Uani 1 1 d . . . . .
H19 H 0.7163 0.0763 0.8350 0.029 Uiso 1 1 calc R U . . .
C20 C 0.9076(6) 0.1347(3) 0.8314(3) 0.0413(12) Uani 1 1 d . . . . .
H20A H 0.9880 0.1054 0.8683 0.050 Uiso 1 1 calc R U . . .
H20B H 0.9264 0.1337 0.7840 0.050 Uiso 1 1 calc R U . . .
C21 C 0.9510(8) 0.1962(3) 0.8651(5) 0.067(2) Uani 1 1 d . . . . .
H21A H 0.9627 0.2233 0.8264 0.080 Uiso 1 1 calc R U . . .
H21B H 1.0638 0.1940 0.9099 0.080 Uiso 1 1 calc R U . . .
C22 C 0.8288(6) 0.2259(2) 0.8917(3) 0.0291(9) Uani 1 1 d . . . . .
H22 H 0.8563 0.2251 0.9454 0.035 Uiso 1 1 calc R U . . .
C23 C 0.6814(6) 0.2538(2) 0.8434(2) 0.0309(9) Uani 1 1 d . . . . .
H23 H 0.6148 0.2719 0.8663 0.037 Uiso 1 1 calc R U . . .
C24 C 0.6150(10) 0.2586(3) 0.7571(3) 0.063(2) Uani 1 1 d . . . . .
H24A H 0.5081 0.2825 0.7372 0.076 Uiso 1 1 calc R U . . .
H24B H 0.6984 0.2819 0.7453 0.076 Uiso 1 1 calc R U . . .
C25 C 0.5807(8) 0.1993(2) 0.7142(3) 0.0423(12) Uani 1 1 d . . . . .
H25A H 0.6663 0.1943 0.6935 0.051 Uiso 1 1 calc R U . . .
H25B H 0.4680 0.2022 0.6695 0.051 Uiso 1 1 calc R U . . .
C26 C 0.1922(5) 0.0533(2) 0.6872(2) 0.0270(8) Uani 1 1 d . . . . .
H26 H 0.2435 0.0849 0.7239 0.032 Uiso 1 1 calc R U . . .
C27 C 0.1211(6) 0.0027(2) 0.7086(3) 0.0322(9) Uani 1 1 d . . . . .
H27 H 0.1245 0.0023 0.7588 0.039 Uiso 1 1 calc R U . . .
C28 C 0.0395(8) -0.0512(3) 0.6553(4) 0.0571(17) Uani 1 1 d . . . . .
H28A H -0.0045 -0.0799 0.6823 0.069 Uiso 1 1 calc R U . . .
H28B H -0.0591 -0.0360 0.6090 0.069 Uiso 1 1 calc R U . . .
C29 C 0.1522(9) -0.0849(3) 0.6298(4) 0.070(2) Uani 1 1 d . . . . .
H29A H 0.1201 -0.0750 0.5749 0.084 Uiso 1 1 calc R U . . .
H29B H 0.1332 -0.1292 0.6330 0.084 Uiso 1 1 calc R U . . .
C30 C 0.3388(8) -0.0718(2) 0.6755(3) 0.0407(12) Uani 1 1 d . . . . .
H30 H 0.4054 -0.0987 0.7162 0.049 Uiso 1 1 calc R U . . .
C31 C 0.4168(8) -0.0215(2) 0.6597(3) 0.0382(12) Uani 1 1 d . . . . .
H31 H 0.5358 -0.0173 0.6901 0.046 Uiso 1 1 calc R U . . .
C32 C 0.3319(10) 0.0266(3) 0.5998(3) 0.0618(19) Uani 1 1 d . . . . .
H32A H 0.4182 0.0571 0.6026 0.074 Uiso 1 1 calc R U . . .
H32B H 0.2877 0.0073 0.5481 0.074 Uiso 1 1 calc R U . . .
C33 C 0.1892(7) 0.0589(3) 0.6075(3) 0.0428(12) Uani 1 1 d . . . . .
H33A H 0.0802 0.0423 0.5687 0.051 Uiso 1 1 calc R U . . .
H33B H 0.1937 0.1027 0.5957 0.051 Uiso 1 1 calc R U . . .
N1 N 0.4433(4) 0.10252(14) 0.95664(17) 0.0165(6) Uani 1 1 d . . . . .
N2 N 0.3982(4) 0.04112(14) 0.85961(17) 0.0177(6) Uani 1 1 d . . . . .
N3 N 0.5832(4) 0.19217(14) 0.97476(16) 0.0154(5) Uani 1 1 d . . . . .
Cl1 Cl 0.31242(12) 0.20091(5) 0.79835(5) 0.02486(18) Uani 1 1 d . . . . .
Cl2 Cl 0.65860(15) -0.04563(5) 0.83913(7) 0.0322(2) Uani 1 1 d . . . . .
Ir1 Ir 0.60852(2) 0.16259(2) 0.87514(2) 0.01623(3) Uani 1 1 d . . . . .
Ir2 Ir 0.38746(2) -0.00424(2) 0.76209(2) 0.02001(4) Uani 1 1 d . . . . .
H1 H 0.7533 0.1198 0.9218 0.050 Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.330(5) . ?
C1 N1 1.400(4) . ?
C1 Ir1 2.024(3) . ?
C2 C3 1.344(5) . ?
C2 N1 1.394(5) . ?
C2 H2 0.9500 . ?
C3 N2 1.406(5) . ?
C3 H3 0.9500 . ?
C4 N3 1.295(5) . ?
C4 N1 1.374(5) . ?
C4 C5 1.482(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.399(5) . ?
C6 C11 1.409(5) . ?
C6 N3 1.454(4) . ?
C7 C8 1.393(6) . ?
C7 C12 1.518(5) . ?
C8 C9 1.387(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(5) . ?
C10 H10 0.9500 . ?
C11 C15 1.523(6) . ?
C12 C13 1.529(6) . ?
C12 C14 1.533(6) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.521(6) . ?
C15 C16 1.524(6) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.391(6) . ?
C18 C25 1.524(7) . ?
C18 Ir1 2.186(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.508(6) . ?
C19 Ir1 2.221(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.472(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.510(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.363(7) . ?
C22 Ir1 2.276(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.504(7) . ?
C23 Ir1 2.258(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.497(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.412(6) . ?
C26 C33 1.522(6) . ?
C26 Ir2 2.108(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.522(7) . ?
C27 Ir2 2.100(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.470(10) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.505(9) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.394(7) . ?
C30 Ir2 2.127(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.499(8) . ?
C31 Ir2 2.118(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.491(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
N2 Ir2 2.083(3) . ?
N3 Ir1 2.115(3) . ?
Cl1 Ir1 2.5017(10) . ?
Cl2 Ir2 2.3627(11) . ?
Ir1 H1 1.5164 . ?

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 C1 N1 106.6(3) . . ?
N2 C1 Ir1 141.1(3) . . ?
N1 C1 Ir1 111.9(2) . . ?
C3 C2 N1 104.9(3) . . ?
C3 C2 H2 127.5 . . ?
N1 C2 H2 127.5 . . ?
C2 C3 N2 110.2(3) . . ?
C2 C3 H3 124.9 . . ?
N2 C3 H3 124.9 . . ?
N3 C4 N1 115.5(3) . . ?
N3 C4 C5 126.3(3) . . ?
N1 C4 C5 118.2(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 122.1(3) . . ?
C7 C6 N3 119.5(3) . . ?
C11 C6 N3 118.4(3) . . ?
C8 C7 C6 117.7(4) . . ?
C8 C7 C12 118.9(4) . . ?
C6 C7 C12 123.3(3) . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 121.4(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C6 117.6(4) . . ?
C10 C11 C15 119.8(3) . . ?
C6 C11 C15 122.6(3) . . ?
C7 C12 C13 113.0(4) . . ?
C7 C12 C14 110.5(3) . . ?
C13 C12 C14 109.4(4) . . ?
C7 C12 H12 107.9 . . ?
C13 C12 H12 107.9 . . ?
C14 C12 H12 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C15 C11 112.1(4) . . ?
C17 C15 C16 108.6(4) . . ?
C11 C15 C16 111.8(4) . . ?
C17 C15 H15 108.0 . . ?
C11 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C25 124.3(4) . . ?
C19 C18 Ir1 73.0(2) . . ?
C25 C18 Ir1 111.7(3) . . ?
C19 C18 H18 117.8 . . ?
C25 C18 H18 117.8 . . ?
Ir1 C18 H18 85.2 . . ?
C18 C19 C20 124.6(4) . . ?
C18 C19 Ir1 70.2(2) . . ?
C20 C19 Ir1 112.1(3) . . ?
C18 C19 H19 117.7 . . ?
C20 C19 H19 117.7 . . ?
Ir1 C19 H19 87.7 . . ?
C21 C20 C19 116.8(4) . . ?
C21 C20 H20A 108.1 . . ?
C19 C20 H20A 108.1 . . ?
C21 C20 H20B 108.1 . . ?
C19 C20 H20B 108.1 . . ?
H20A C20 H20B 107.3 . . ?
C20 C21 C22 117.2(4) . . ?
C20 C21 H21A 108.0 . . ?
C22 C21 H21A 108.0 . . ?
C20 C21 H21B 108.0 . . ?
C22 C21 H21B 108.0 . . ?
H21A C21 H21B 107.2 . . ?
C23 C22 C21 123.9(5) . . ?
C23 C22 Ir1 71.8(2) . . ?
C21 C22 Ir1 111.3(3) . . ?
C23 C22 H22 118.0 . . ?
C21 C22 H22 118.0 . . ?
Ir1 C22 H22 86.9 . . ?
C22 C23 C24 125.7(5) . . ?
C22 C23 Ir1 73.2(3) . . ?
C24 C23 Ir1 109.7(3) . . ?
C22 C23 H23 117.1 . . ?
C24 C23 H23 117.1 . . ?
Ir1 C23 H23 86.9 . . ?
C25 C24 C23 115.9(5) . . ?
C25 C24 H24A 108.3 . . ?
C23 C24 H24A 108.3 . . ?
C25 C24 H24B 108.3 . . ?
C23 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C24 C25 C18 117.3(4) . . ?
C24 C25 H25A 108.0 . . ?
C18 C25 H25A 108.0 . . ?
C24 C25 H25B 108.0 . . ?
C18 C25 H25B 108.0 . . ?
H25A C25 H25B 107.2 . . ?
C27 C26 C33 122.2(4) . . ?
C27 C26 Ir2 70.1(3) . . ?
C33 C26 Ir2 113.1(3) . . ?
C27 C26 H26 118.9 . . ?
C33 C26 H26 118.9 . . ?
Ir2 C26 H26 86.9 . . ?
C26 C27 C28 123.4(5) . . ?
C26 C27 Ir2 70.7(3) . . ?
C28 C27 Ir2 111.8(4) . . ?
C26 C27 H27 118.3 . . ?
C28 C27 H27 118.3 . . ?
Ir2 C27 H27 87.5 . . ?
C29 C28 C27 115.2(5) . . ?
C29 C28 H28A 108.5 . . ?
C27 C28 H28A 108.5 . . ?
C29 C28 H28B 108.5 . . ?
C27 C28 H28B 108.5 . . ?
H28A C28 H28B 107.5 . . ?
C28 C29 C30 114.8(5) . . ?
C28 C29 H29A 108.6 . . ?
C30 C29 H29A 108.6 . . ?
C28 C29 H29B 108.6 . . ?
C30 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C31 C30 C29 122.0(6) . . ?
C31 C30 Ir2 70.5(3) . . ?
C29 C30 Ir2 113.0(4) . . ?
C31 C30 H30 119.0 . . ?
C29 C30 H30 119.0 . . ?
Ir2 C30 H30 86.7 . . ?
C30 C31 C32 126.5(6) . . ?
C30 C31 Ir2 71.2(3) . . ?
C32 C31 Ir2 111.6(3) . . ?
C30 C31 H31 116.7 . . ?
C32 C31 H31 116.7 . . ?
Ir2 C31 H31 87.1 . . ?
C33 C32 C31 114.6(5) . . ?
C33 C32 H32A 108.6 . . ?
C31 C32 H32A 108.6 . . ?
C33 C32 H32B 108.6 . . ?
C31 C32 H32B 108.6 . . ?
H32A C32 H32B 107.6 . . ?
C32 C33 C26 113.9(4) . . ?
C32 C33 H33A 108.8 . . ?
C26 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
C26 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C4 N1 C2 130.6(3) . . ?
C4 N1 C1 119.3(3) . . ?
C2 N1 C1 109.9(3) . . ?
C1 N2 C3 108.3(3) . . ?
C1 N2 Ir2 130.1(2) . . ?
C3 N2 Ir2 121.6(2) . . ?
C4 N3 C6 120.1(3) . . ?
C4 N3 Ir1 114.8(2) . . ?
C6 N3 Ir1 125.0(2) . . ?
C1 Ir1 N3 78.43(13) . . ?
C1 Ir1 C18 100.85(15) . . ?
N3 Ir1 C18 167.76(15) . . ?
C1 Ir1 C19 98.67(14) . . ?
N3 Ir1 C19 155.39(14) . . ?
C18 Ir1 C19 36.79(16) . . ?
C1 Ir1 C23 163.70(16) . . ?
N3 Ir1 C23 96.99(15) . . ?
C18 Ir1 C23 80.28(16) . . ?
C19 Ir1 C23 91.88(17) . . ?
C1 Ir1 C22 159.96(16) . . ?
N3 Ir1 C22 95.44(13) . . ?
C18 Ir1 C22 89.11(16) . . ?
C19 Ir1 C22 78.90(15) . . ?
C23 Ir1 C22 34.98(17) . . ?
C1 Ir1 Cl1 80.92(10) . . ?
N3 Ir1 Cl1 87.03(8) . . ?
C18 Ir1 Cl1 80.82(12) . . ?
C19 Ir1 Cl1 116.89(11) . . ?
C23 Ir1 Cl1 83.24(13) . . ?
C22 Ir1 Cl1 118.11(13) . . ?
C1 Ir1 H1 79.4 . . ?
N3 Ir1 H1 92.3 . . ?
C18 Ir1 H1 99.6 . . ?
C19 Ir1 H1 63.3 . . ?
C23 Ir1 H1 116.6 . . ?
C22 Ir1 H1 81.8 . . ?
Cl1 Ir1 H1 160.1 . . ?
N2 Ir2 C27 91.08(16) . . ?
N2 Ir2 C26 92.18(15) . . ?
C27 Ir2 C26 39.21(17) . . ?
N2 Ir2 C31 159.93(17) . . ?
C27 Ir2 C31 96.2(2) . . ?
C26 Ir2 C31 81.90(19) . . ?
N2 Ir2 C30 161.74(18) . . ?
C27 Ir2 C30 82.0(2) . . ?
C26 Ir2 C30 93.0(2) . . ?
C31 Ir2 C30 38.3(2) . . ?
N2 Ir2 Cl2 88.52(9) . . ?
C27 Ir2 Cl2 158.53(13) . . ?
C26 Ir2 Cl2 162.25(12) . . ?
C31 Ir2 Cl2 91.42(16) . . ?
C30 Ir2 Cl2 91.80(16) . . ?

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 C2 C3 N2 0.0(4) . . . . ?
C11 C6 C7 C8 3.0(5) . . . . ?
N3 C6 C7 C8 -175.0(3) . . . . ?
C11 C6 C7 C12 -174.2(3) . . . . ?
N3 C6 C7 C12 7.8(5) . . . . ?
C6 C7 C8 C9 -1.9(6) . . . . ?
C12 C7 C8 C9 175.4(4) . . . . ?
C7 C8 C9 C10 -0.2(7) . . . . ?
C8 C9 C10 C11 1.3(7) . . . . ?
C9 C10 C11 C6 -0.3(6) . . . . ?
C9 C10 C11 C15 -179.1(4) . . . . ?
C7 C6 C11 C10 -1.9(5) . . . . ?
N3 C6 C11 C10 176.1(3) . . . . ?
C7 C6 C11 C15 176.8(3) . . . . ?
N3 C6 C11 C15 -5.2(5) . . . . ?
C8 C7 C12 C13 57.8(5) . . . . ?
C6 C7 C12 C13 -125.1(4) . . . . ?
C8 C7 C12 C14 -65.2(5) . . . . ?
C6 C7 C12 C14 111.9(4) . . . . ?
C10 C11 C15 C17 -44.0(5) . . . . ?
C6 C11 C15 C17 137.3(4) . . . . ?
C10 C11 C15 C16 78.3(5) . . . . ?
C6 C11 C15 C16 -100.4(5) . . . . ?
C25 C18 C19 C20 1.4(6) . . . . ?
Ir1 C18 C19 C20 -103.7(4) . . . . ?
C25 C18 C19 Ir1 105.1(4) . . . . ?
C18 C19 C20 C21 59.3(7) . . . . ?
Ir1 C19 C20 C21 -21.3(7) . . . . ?
C19 C20 C21 C22 12.7(10) . . . . ?
C20 C21 C22 C23 -79.6(8) . . . . ?
C20 C21 C22 Ir1 2.2(8) . . . . ?
C21 C22 C23 C24 1.3(7) . . . . ?
Ir1 C22 C23 C24 -102.5(4) . . . . ?
C21 C22 C23 Ir1 103.9(4) . . . . ?
C22 C23 C24 C25 60.2(8) . . . . ?
Ir1 C23 C24 C25 -22.9(7) . . . . ?
C23 C24 C25 C18 11.7(9) . . . . ?
C19 C18 C25 C24 -77.4(7) . . . . ?
Ir1 C18 C25 C24 6.3(7) . . . . ?
C33 C26 C27 C28 1.5(8) . . . . ?
Ir2 C26 C27 C28 -103.9(5) . . . . ?
C33 C26 C27 Ir2 105.4(4) . . . . ?
C26 C27 C28 C29 60.3(8) . . . . ?
Ir2 C27 C28 C29 -20.4(7) . . . . ?
C27 C28 C29 C30 15.1(9) . . . . ?
C28 C29 C30 C31 -83.2(8) . . . . ?
C28 C29 C30 Ir2 -2.6(8) . . . . ?
C29 C30 C31 C32 2.1(8) . . . . ?
Ir2 C30 C31 C32 -103.4(5) . . . . ?
C29 C30 C31 Ir2 105.5(5) . . . . ?
C30 C31 C32 C33 57.1(8) . . . . ?
Ir2 C31 C32 C33 -25.0(8) . . . . ?
C31 C32 C33 C26 19.2(8) . . . . ?
C27 C26 C33 C32 -84.6(7) . . . . ?
Ir2 C26 C33 C32 -4.2(6) . . . . ?
N3 C4 N1 C2 -174.1(4) . . . . ?
C5 C4 N1 C2 5.1(6) . . . . ?
N3 C4 N1 C1 0.3(5) . . . . ?
C5 C4 N1 C1 179.5(3) . . . . ?
C3 C2 N1 C4 174.8(4) . . . . ?
C3 C2 N1 C1 0.0(4) . . . . ?
N2 C1 N1 C4 -175.4(3) . . . . ?
Ir1 C1 N1 C4 -1.0(4) . . . . ?
N2 C1 N1 C2 0.0(4) . . . . ?
Ir1 C1 N1 C2 174.5(2) . . . . ?
N1 C1 N2 C3 0.0(4) . . . . ?
Ir1 C1 N2 C3 -171.8(3) . . . . ?
N1 C1 N2 Ir2 180.0(2) . . . . ?
Ir1 C1 N2 Ir2 8.2(6) . . . . ?
C2 C3 N2 C1 0.0(4) . . . . ?
C2 C3 N2 Ir2 -180.0(3) . . . . ?
N1 C4 N3 C6 -177.0(3) . . . . ?
C5 C4 N3 C6 3.9(5) . . . . ?
N1 C4 N3 Ir1 0.5(4) . . . . ?
C5 C4 N3 Ir1 -178.6(3) . . . . ?
C7 C6 N3 C4 -90.7(4) . . . . ?
C11 C6 N3 C4 91.3(4) . . . . ?
C7 C6 N3 Ir1 92.0(4) . . . . ?
C11 C6 N3 Ir1 -86.0(4) . . . . ?

_refine_diff_density_max         4.805
_refine_diff_density_min         -3.082
_refine_diff_density_rms         0.168

_shelxl_version_number           2013-4

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

data_pbfh140901
_database_code_depnum_ccdc_archive 'CCDC 1039713'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H68 Ir2 N6'
_chemical_formula_sum            'C50 H68 Ir2 N6'
_chemical_formula_weight         1137.50

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'
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                   12.2904(3)
_cell_length_b                   13.3290(5)
_cell_length_c                   19.4944(6)
_cell_angle_alpha                86.542(2)
_cell_angle_beta                 72.600(2)
_cell_angle_gamma                62.575(4)
_cell_volume                     2693.61(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    30741
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    4.970
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28056
_exptl_absorpt_correction_T_max  0.33442
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29513
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.099
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             12243
_reflns_number_gt                9499
_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       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'Superflip (Palatinus, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0656P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12243
_refine_ls_number_parameters     533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1290(5) 0.1457(4) 0.6208(3) 0.0215(11) Uani 1 1 d . . . . .
C2 C -0.0244(5) 0.0931(5) 0.6741(3) 0.0245(12) Uani 1 1 d . . . . .
H2 H -0.0940 0.0885 0.7095 0.029 Uiso 1 1 calc R U . . .
C3 C 0.0366(5) 0.0364(5) 0.6074(3) 0.0261(12) Uani 1 1 d . . . . .
H3 H 0.0178 -0.0145 0.5871 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2209(5) 0.0171(4) 0.5045(3) 0.0223(11) Uani 1 1 d . . . . .
C5 C 0.3553(5) -0.0039(5) 0.4920(3) 0.0287(13) Uani 1 1 d . . . . .
H5A H 0.4033 -0.0766 0.5098 0.043 Uiso 1 1 calc R U . . .
H5B H 0.3546 0.0573 0.5179 0.043 Uiso 1 1 calc R U . . .
H5C H 0.3966 -0.0064 0.4403 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2508(5) -0.0679(5) 0.3930(3) 0.0209(11) Uani 1 1 d . . . . .
C7 C 0.3050(5) -0.1881(5) 0.3871(3) 0.0253(12) Uani 1 1 d . . . . .
C8 C 0.3655(5) -0.2442(5) 0.3179(3) 0.0300(14) Uani 1 1 d . . . . .
H8 H 0.4015 -0.3245 0.3124 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3746(5) -0.1848(5) 0.2559(3) 0.0300(13) Uani 1 1 d . . . . .
H9 H 0.4175 -0.2245 0.2092 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3198(5) -0.0675(5) 0.2644(3) 0.0269(12) Uani 1 1 d . . . . .
H10 H 0.3256 -0.0274 0.2227 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2564(5) -0.0065(5) 0.3320(3) 0.0230(11) Uani 1 1 d . . . . .
C12 C 0.2898(5) -0.2523(5) 0.4533(3) 0.0307(13) Uani 1 1 d . . . . .
H12 H 0.3024 -0.2166 0.4921 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1532(6) -0.2391(6) 0.4809(3) 0.0365(14) Uani 1 1 d . . . . .
H13A H 0.1389 -0.2761 0.4450 0.055 Uiso 1 1 calc R U . . .
H13B H 0.0908 -0.1583 0.4891 0.055 Uiso 1 1 calc R U . . .
H13C H 0.1423 -0.2745 0.5263 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3877(6) -0.3783(5) 0.4420(4) 0.0426(16) Uani 1 1 d . . . . .
H14A H 0.3803 -0.4112 0.4885 0.064 Uiso 1 1 calc R U . . .
H14B H 0.4749 -0.3866 0.4214 0.064 Uiso 1 1 calc R U . . .
H14C H 0.3707 -0.4179 0.4090 0.064 Uiso 1 1 calc R U . . .
C15 C 0.1944(6) 0.1208(5) 0.3384(3) 0.0316(13) Uani 1 1 d . . . . .
H15 H 0.1521 0.1477 0.3909 0.038 Uiso 1 1 calc R U . . .
C16 C 0.0894(6) 0.1729(6) 0.3006(4) 0.0450(17) Uani 1 1 d . . . . .
H16A H 0.1282 0.1478 0.2489 0.068 Uiso 1 1 calc R U . . .
H16B H 0.0495 0.2559 0.3073 0.068 Uiso 1 1 calc R U . . .
H16C H 0.0237 0.1481 0.3215 0.068 Uiso 1 1 calc R U . . .
C17 C 0.2959(7) 0.1630(6) 0.3090(4) 0.0502(18) Uani 1 1 d . . . . .
H17A H 0.3577 0.1343 0.3365 0.075 Uiso 1 1 calc R U . . .
H17B H 0.2532 0.2461 0.3139 0.075 Uiso 1 1 calc R U . . .
H17C H 0.3414 0.1352 0.2580 0.075 Uiso 1 1 calc R U . . .
C18 C 0.0956(5) 0.3755(5) 0.5573(3) 0.0304(13) Uani 1 1 d . . . . .
H18 H 0.0268 0.3632 0.5874 0.036 Uiso 1 1 calc R U . . .
C19 C 0.1990(6) 0.2860(5) 0.5083(3) 0.0303(13) Uani 1 1 d . . . . .
H19 H 0.1936 0.2177 0.5047 0.036 Uiso 1 1 calc R U . . .
C20 C 0.3195(6) 0.2909(6) 0.4602(3) 0.0364(14) Uani 1 1 d . . . . .
H20A H 0.3853 0.2134 0.4383 0.044 Uiso 1 1 calc R U . . .
H20B H 0.2979 0.3386 0.4205 0.044 Uiso 1 1 calc R U . . .
C21 C 0.3761(6) 0.3386(6) 0.5008(4) 0.0413(16) Uani 1 1 d . . . . .
H21A H 0.3389 0.4217 0.4978 0.050 Uiso 1 1 calc R U . . .
H21B H 0.4702 0.3050 0.4773 0.050 Uiso 1 1 calc R U . . .
C22 C 0.3497(6) 0.3143(5) 0.5811(3) 0.0321(14) Uani 1 1 d . . . . .
H22 H 0.4076 0.2441 0.5934 0.038 Uiso 1 1 calc R U . . .
C23 C 0.2442(5) 0.3912(5) 0.6366(3) 0.0290(13) Uani 1 1 d . . . . .
H23 H 0.2378 0.3716 0.6848 0.035 Uiso 1 1 calc R U . . .
C24 C 0.1424(6) 0.5008(5) 0.6252(4) 0.0374(15) Uani 1 1 d . . . . .
H24A H 0.1776 0.5554 0.6131 0.045 Uiso 1 1 calc R U . . .
H24B H 0.0705 0.5316 0.6709 0.045 Uiso 1 1 calc R U . . .
C25 C 0.0890(6) 0.4912(5) 0.5644(3) 0.0362(15) Uani 1 1 d . . . . .
H25A H -0.0016 0.5507 0.5750 0.043 Uiso 1 1 calc R U . . .
H25B H 0.1393 0.5045 0.5180 0.043 Uiso 1 1 calc R U . . .
C26 C 0.1789(4) 0.1848(4) 0.7625(3) 0.0205(11) Uani 1 1 d . . . . .
C27 C 0.3873(5) 0.1354(5) 0.7165(3) 0.0259(12) Uani 1 1 d . . . . .
H27 H 0.4668 0.1248 0.6831 0.031 Uiso 1 1 calc R U . . .
C28 C 0.3696(5) 0.1108(5) 0.7853(3) 0.0273(13) Uani 1 1 d . . . . .
H28 H 0.4332 0.0795 0.8094 0.033 Uiso 1 1 calc R U . . .
C29 C 0.1924(5) 0.1040(5) 0.8818(3) 0.0245(12) Uani 1 1 d . . . . .
C30 C 0.0906(5) 0.0698(6) 0.8881(3) 0.0325(14) Uani 1 1 d . . . . .
H30A H 0.1293 -0.0050 0.8618 0.049 Uiso 1 1 calc R U . . .
H30B H 0.0257 0.1256 0.8674 0.049 Uiso 1 1 calc R U . . .
H30C H 0.0498 0.0662 0.9391 0.049 Uiso 1 1 calc R U . . .
C31 C 0.2276(5) 0.0410(5) 0.9920(3) 0.0266(12) Uani 1 1 d . . . . .
C32 C 0.3156(6) -0.0732(5) 0.9911(3) 0.0329(14) Uani 1 1 d . . . . .
C33 C 0.2990(6) -0.1272(6) 1.0547(4) 0.0415(16) Uani 1 1 d . . . . .
H33 H 0.3581 -0.2043 1.0557 0.050 Uiso 1 1 calc R U . . .
C34 C 0.1977(6) -0.0692(6) 1.1155(4) 0.0432(17) Uani 1 1 d . . . . .
H34 H 0.1856 -0.1074 1.1576 0.052 Uiso 1 1 calc R U . . .
C35 C 0.1132(6) 0.0444(6) 1.1159(3) 0.0370(15) Uani 1 1 d . . . . .
H35 H 0.0465 0.0838 1.1591 0.044 Uiso 1 1 calc R U . . .
C36 C 0.1243(5) 0.1017(5) 1.0542(3) 0.0295(13) Uani 1 1 d . . . . .
C37 C 0.4291(6) -0.1360(6) 0.9241(4) 0.0439(17) Uani 1 1 d . . . . .
H37 H 0.4012 -0.1015 0.8815 0.053 Uiso 1 1 calc R U . . .
C38 C 0.5380(7) -0.1136(8) 0.9245(5) 0.072(3) Uani 1 1 d . . . . .
H38A H 0.5086 -0.0316 0.9272 0.108 Uiso 1 1 calc R U . . .
H38B H 0.6095 -0.1499 0.8800 0.108 Uiso 1 1 calc R U . . .
H38C H 0.5669 -0.1448 0.9663 0.108 Uiso 1 1 calc R U . . .
C39 C 0.4665(9) -0.2613(8) 0.9155(5) 0.087(3) Uani 1 1 d . . . . .
H39A H 0.4947 -0.2984 0.9564 0.131 Uiso 1 1 calc R U . . .
H39B H 0.5369 -0.2966 0.8705 0.131 Uiso 1 1 calc R U . . .
H39C H 0.3921 -0.2696 0.9139 0.131 Uiso 1 1 calc R U . . .
C40 C 0.0315(6) 0.2266(6) 1.0574(3) 0.0382(15) Uani 1 1 d . . . . .
H40 H 0.0517 0.2517 1.0078 0.046 Uiso 1 1 calc R U . . .
C41 C 0.0496(8) 0.2957(7) 1.1072(5) 0.072(3) Uani 1 1 d . . . . .
H41A H 0.0304 0.2727 1.1563 0.108 Uiso 1 1 calc R U . . .
H41B H -0.0087 0.3764 1.1072 0.108 Uiso 1 1 calc R U . . .
H41C H 0.1388 0.2831 1.0906 0.108 Uiso 1 1 calc R U . . .
C42 C -0.1104(6) 0.2482(7) 1.0805(4) 0.057(2) Uani 1 1 d . . . . .
H42A H -0.1207 0.2045 1.0464 0.085 Uiso 1 1 calc R U . . .
H42B H -0.1674 0.3293 1.0805 0.085 Uiso 1 1 calc R U . . .
H42C H -0.1326 0.2245 1.1291 0.085 Uiso 1 1 calc R U . . .
C43 C -0.0394(6) 0.4293(5) 0.8128(3) 0.0315(13) Uani 1 1 d . . . . .
H43 H 0.0474 0.4080 0.7855 0.038 Uiso 1 1 calc R U . . .
C44 C -0.0649(5) 0.3599(5) 0.8663(3) 0.0325(14) Uani 1 1 d . . . . .
H44 H 0.0074 0.2977 0.8751 0.039 Uiso 1 1 calc R U . . .
C45 C -0.1947(5) 0.3753(6) 0.9101(3) 0.0385(15) Uani 1 1 d . . . . .
H45A H -0.2340 0.4393 0.9476 0.046 Uiso 1 1 calc R U . . .
H45B H -0.1849 0.3060 0.9348 0.046 Uiso 1 1 calc R U . . .
C46 C -0.2869(5) 0.3994(5) 0.8643(3) 0.0356(14) Uani 1 1 d . . . . .
H46A H -0.3499 0.3716 0.8880 0.043 Uiso 1 1 calc R U . . .
H46B H -0.3353 0.4824 0.8626 0.043 Uiso 1 1 calc R U . . .
C47 C -0.2167(5) 0.3437(5) 0.7883(3) 0.0282(13) Uani 1 1 d . . . . .
H47 H -0.2005 0.2680 0.7793 0.034 Uiso 1 1 calc R U . . .
C48 C -0.1745(5) 0.3968(5) 0.7309(3) 0.0282(13) Uani 1 1 d . . . . .
H48 H -0.1326 0.3553 0.6847 0.034 Uiso 1 1 calc R U . . .
C49 C -0.1901(6) 0.5162(5) 0.7360(4) 0.0366(15) Uani 1 1 d . . . . .
H49A H -0.2817 0.5714 0.7438 0.044 Uiso 1 1 calc R U . . .
H49B H -0.1390 0.5289 0.6896 0.044 Uiso 1 1 calc R U . . .
C50 C -0.1470(6) 0.5382(5) 0.7974(4) 0.0355(14) Uani 1 1 d . . . . .
H50A H -0.2217 0.5695 0.8417 0.043 Uiso 1 1 calc R U . . .
H50B H -0.1159 0.5954 0.7841 0.043 Uiso 1 1 calc R U . . .
N1 N 0.0325(4) 0.1595(4) 0.6819(2) 0.0208(9) Uani 1 1 d . . . . .
N2 N 0.1328(4) 0.0679(4) 0.5744(2) 0.0208(9) Uani 1 1 d . . . . .
N3 N 0.1743(4) -0.0086(4) 0.4631(2) 0.0213(9) Uani 1 1 d . . . . .
N4 N 0.2710(4) 0.1787(4) 0.7018(2) 0.0233(10) Uani 1 1 d . . . . .
N5 N 0.2400(4) 0.1403(4) 0.8145(2) 0.0226(10) Uani 1 1 d . . . . .
N6 N 0.2516(4) 0.0958(4) 0.9274(2) 0.0260(10) Uani 1 1 d . . . . .
Ir1 Ir 0.21004(2) 0.25125(2) 0.61479(2) 0.02131(7) Uani 1 1 d . . . . .
Ir2 Ir -0.00769(2) 0.27731(2) 0.76142(2) 0.02127(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.357(7) . ?
C1 N2 1.392(6) . ?
C1 Ir1 2.046(5) . ?
C2 C3 1.356(8) . ?
C2 N1 1.394(7) . ?
C2 H2 0.9500 . ?
C3 N2 1.399(7) . ?
C3 H3 0.9500 . ?
C4 N3 1.260(6) . ?
C4 N2 1.428(7) . ?
C4 C5 1.486(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.405(7) . ?
C6 C7 1.420(7) . ?
C6 N3 1.432(7) . ?
C7 C8 1.393(8) . ?
C7 C12 1.518(8) . ?
C8 C9 1.408(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(7) . ?
C10 H10 0.9500 . ?
C11 C15 1.501(8) . ?
C12 C13 1.530(8) . ?
C12 C14 1.531(8) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.541(8) . ?
C15 C17 1.543(9) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.402(8) . ?
C18 C25 1.520(8) . ?
C18 Ir1 2.133(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.526(8) . ?
C19 Ir1 2.131(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.520(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.547(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.405(8) . ?
C22 Ir1 2.162(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.481(8) . ?
C23 Ir1 2.183(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.553(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 N4 1.347(7) . ?
C26 N5 1.383(6) . ?
C26 Ir2 2.050(4) . ?
C27 C28 1.338(8) . ?
C27 N4 1.387(6) . ?
C27 H27 0.9500 . ?
C28 N5 1.387(6) . ?
C28 H28 0.9500 . ?
C29 N6 1.278(6) . ?
C29 N5 1.422(7) . ?
C29 C30 1.489(7) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.402(8) . ?
C31 C36 1.410(8) . ?
C31 N6 1.439(7) . ?
C32 C33 1.403(9) . ?
C32 C37 1.522(9) . ?
C33 C34 1.376(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(10) . ?
C34 H34 0.9500 . ?
C35 C36 1.392(8) . ?
C35 H35 0.9500 . ?
C36 C40 1.516(9) . ?
C37 C38 1.501(10) . ?
C37 C39 1.519(11) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.506(9) . ?
C40 C42 1.553(9) . ?
C40 H40 1.0000 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.412(9) . ?
C43 C50 1.537(8) . ?
C43 Ir2 2.132(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.490(8) . ?
C44 Ir2 2.141(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.555(8) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.506(8) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.385(8) . ?
C47 Ir2 2.194(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.518(8) . ?
C48 Ir2 2.168(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.537(8) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
N1 Ir2 2.058(4) . ?
N4 Ir1 2.066(4) . ?
Ir1 Ir2 3.1844(3) . ?

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 C1 N2 105.3(4) . . ?
N1 C1 Ir1 116.8(4) . . ?
N2 C1 Ir1 137.3(4) . . ?
C3 C2 N1 108.3(5) . . ?
C3 C2 H2 125.8 . . ?
N1 C2 H2 125.8 . . ?
C2 C3 N2 106.3(5) . . ?
C2 C3 H3 126.9 . . ?
N2 C3 H3 126.9 . . ?
N3 C4 N2 114.8(4) . . ?
N3 C4 C5 129.0(5) . . ?
N2 C4 C5 116.2(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 122.0(5) . . ?
C11 C6 N3 119.7(5) . . ?
C7 C6 N3 117.8(5) . . ?
C8 C7 C6 117.5(5) . . ?
C8 C7 C12 121.2(5) . . ?
C6 C7 C12 121.2(5) . . ?
C7 C8 C9 121.7(5) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 118.8(5) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 122.3(5) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C6 117.8(5) . . ?
C10 C11 C15 120.3(5) . . ?
C6 C11 C15 121.9(5) . . ?
C7 C12 C13 110.5(5) . . ?
C7 C12 C14 114.3(5) . . ?
C13 C12 C14 109.7(5) . . ?
C7 C12 H12 107.4 . . ?
C13 C12 H12 107.4 . . ?
C14 C12 H12 107.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 C16 112.0(5) . . ?
C11 C15 C17 111.1(5) . . ?
C16 C15 C17 110.6(5) . . ?
C11 C15 H15 107.7 . . ?
C16 C15 H15 107.7 . . ?
C17 C15 H15 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C25 122.7(6) . . ?
C19 C18 Ir1 70.7(3) . . ?
C25 C18 Ir1 114.2(4) . . ?
C19 C18 H18 118.7 . . ?
C25 C18 H18 118.7 . . ?
Ir1 C18 H18 85.2 . . ?
C18 C19 C20 124.4(6) . . ?
C18 C19 Ir1 70.9(3) . . ?
C20 C19 Ir1 111.1(4) . . ?
C18 C19 H19 117.8 . . ?
C20 C19 H19 117.8 . . ?
Ir1 C19 H19 88.0 . . ?
C21 C20 C19 113.0(5) . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 C22 112.6(5) . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 123.1(6) . . ?
C23 C22 Ir1 71.9(3) . . ?
C21 C22 Ir1 112.5(4) . . ?
C23 C22 H22 118.4 . . ?
C21 C22 H22 118.4 . . ?
Ir1 C22 H22 85.6 . . ?
C22 C23 C24 124.5(6) . . ?
C22 C23 Ir1 70.3(3) . . ?
C24 C23 Ir1 110.6(4) . . ?
C22 C23 H23 117.7 . . ?
C24 C23 H23 117.7 . . ?
Ir1 C23 H23 89.1 . . ?
C23 C24 C25 113.4(5) . . ?
C23 C24 H24A 108.9 . . ?
C25 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C25 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C18 C25 C24 111.9(5) . . ?
C18 C25 H25A 109.2 . . ?
C24 C25 H25A 109.2 . . ?
C18 C25 H25B 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
N4 C26 N5 106.3(4) . . ?
N4 C26 Ir2 116.3(3) . . ?
N5 C26 Ir2 136.2(4) . . ?
C28 C27 N4 109.1(5) . . ?
C28 C27 H27 125.5 . . ?
N4 C27 H27 125.5 . . ?
C27 C28 N5 106.5(4) . . ?
C27 C28 H28 126.7 . . ?
N5 C28 H28 126.7 . . ?
N6 C29 N5 114.7(5) . . ?
N6 C29 C30 128.0(5) . . ?
N5 C29 C30 117.0(4) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C36 121.9(5) . . ?
C32 C31 N6 116.8(5) . . ?
C36 C31 N6 121.2(5) . . ?
C31 C32 C33 118.1(6) . . ?
C31 C32 C37 121.1(6) . . ?
C33 C32 C37 120.8(6) . . ?
C34 C33 C32 120.4(6) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.7(6) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C36 121.2(6) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C31 117.5(6) . . ?
C35 C36 C40 119.5(5) . . ?
C31 C36 C40 122.9(5) . . ?
C38 C37 C39 113.8(7) . . ?
C38 C37 C32 108.9(6) . . ?
C39 C37 C32 112.9(6) . . ?
C38 C37 H37 106.9 . . ?
C39 C37 H37 106.9 . . ?
C32 C37 H37 106.9 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 C36 110.6(5) . . ?
C41 C40 C42 110.8(6) . . ?
C36 C40 C42 111.6(6) . . ?
C41 C40 H40 107.9 . . ?
C36 C40 H40 107.9 . . ?
C42 C40 H40 107.9 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C50 122.4(5) . . ?
C44 C43 Ir2 71.0(3) . . ?
C50 C43 Ir2 114.3(4) . . ?
C44 C43 H43 118.8 . . ?
C50 C43 H43 118.8 . . ?
Ir2 C43 H43 84.9 . . ?
C43 C44 C45 126.0(5) . . ?
C43 C44 Ir2 70.4(3) . . ?
C45 C44 Ir2 111.0(4) . . ?
C43 C44 H44 117.0 . . ?
C45 C44 H44 117.0 . . ?
Ir2 C44 H44 88.6 . . ?
C44 C45 C46 113.1(5) . . ?
C44 C45 H45A 108.9 . . ?
C46 C45 H45A 108.9 . . ?
C44 C45 H45B 108.9 . . ?
C46 C45 H45B 108.9 . . ?
H45A C45 H45B 107.8 . . ?
C47 C46 C45 112.7(4) . . ?
C47 C46 H46A 109.1 . . ?
C45 C46 H46A 109.1 . . ?
C47 C46 H46B 109.1 . . ?
C45 C46 H46B 109.0 . . ?
H46A C46 H46B 107.8 . . ?
C48 C47 C46 123.5(5) . . ?
C48 C47 Ir2 70.5(3) . . ?
C46 C47 Ir2 112.2(4) . . ?
C48 C47 H47 118.3 . . ?
C46 C47 H47 118.3 . . ?
Ir2 C47 H47 87.3 . . ?
C47 C48 C49 125.1(5) . . ?
C47 C48 Ir2 72.5(3) . . ?
C49 C48 Ir2 110.4(3) . . ?
C47 C48 H48 117.4 . . ?
C49 C48 H48 117.4 . . ?
Ir2 C48 H48 87.0 . . ?
C48 C49 C50 113.0(5) . . ?
C48 C49 H49A 109.0 . . ?
C50 C49 H49A 109.0 . . ?
C48 C49 H49B 109.0 . . ?
C50 C49 H49B 109.0 . . ?
H49A C49 H49B 107.8 . . ?
C49 C50 C43 111.9(5) . . ?
C49 C50 H50A 109.2 . . ?
C43 C50 H50A 109.2 . . ?
C49 C50 H50B 109.2 . . ?
C43 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
C1 N1 C2 110.1(4) . . ?
C1 N1 Ir2 116.0(3) . . ?
C2 N1 Ir2 133.7(4) . . ?
C1 N2 C3 110.0(4) . . ?
C1 N2 C4 129.5(4) . . ?
C3 N2 C4 120.5(4) . . ?
C4 N3 C6 122.5(4) . . ?
C26 N4 C27 108.8(4) . . ?
C26 N4 Ir1 116.5(3) . . ?
C27 N4 Ir1 134.1(4) . . ?
C26 N5 C28 109.2(4) . . ?
C26 N5 C29 128.0(4) . . ?
C28 N5 C29 121.4(4) . . ?
C29 N6 C31 119.4(5) . . ?
C1 Ir1 N4 88.11(18) . . ?
C1 Ir1 C19 91.2(2) . . ?
N4 Ir1 C19 163.3(2) . . ?
C1 Ir1 C18 96.8(2) . . ?
N4 Ir1 C18 158.1(2) . . ?
C19 Ir1 C18 38.4(2) . . ?
C1 Ir1 C22 159.8(2) . . ?
N4 Ir1 C22 93.44(19) . . ?
C19 Ir1 C22 81.6(2) . . ?
C18 Ir1 C22 89.3(2) . . ?
C1 Ir1 C23 162.4(2) . . ?
N4 Ir1 C23 87.9(2) . . ?
C19 Ir1 C23 97.5(2) . . ?
C18 Ir1 C23 81.0(2) . . ?
C22 Ir1 C23 37.7(2) . . ?
C1 Ir1 Ir2 63.58(14) . . ?
N4 Ir1 Ir2 63.16(11) . . ?
C19 Ir1 Ir2 130.66(16) . . ?
C18 Ir1 Ir2 99.94(17) . . ?
C22 Ir1 Ir2 134.41(17) . . ?
C23 Ir1 Ir2 99.46(16) . . ?
C26 Ir2 N1 87.95(18) . . ?
C26 Ir2 C43 95.2(2) . . ?
N1 Ir2 C43 160.7(2) . . ?
C26 Ir2 C44 91.5(2) . . ?
N1 Ir2 C44 160.6(2) . . ?
C43 Ir2 C44 38.6(2) . . ?
C26 Ir2 C48 161.2(2) . . ?
N1 Ir2 C48 89.71(18) . . ?
C43 Ir2 C48 81.2(2) . . ?
C44 Ir2 C48 96.8(2) . . ?
C26 Ir2 C47 161.8(2) . . ?
N1 Ir2 C47 93.50(19) . . ?
C43 Ir2 C47 89.4(2) . . ?
C44 Ir2 C47 81.1(2) . . ?
C48 Ir2 C47 37.0(2) . . ?
C26 Ir2 Ir1 63.77(15) . . ?
N1 Ir2 Ir1 63.49(12) . . ?
C43 Ir2 Ir1 100.93(17) . . ?
C44 Ir2 Ir1 132.80(17) . . ?
C48 Ir2 Ir1 98.62(16) . . ?
C47 Ir2 Ir1 132.57(15) . . ?

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 C2 C3 N2 0.6(6) . . . . ?
C11 C6 C7 C8 0.4(7) . . . . ?
N3 C6 C7 C8 172.1(4) . . . . ?
C11 C6 C7 C12 -175.6(5) . . . . ?
N3 C6 C7 C12 -3.9(7) . . . . ?
C6 C7 C8 C9 0.9(7) . . . . ?
C12 C7 C8 C9 176.9(5) . . . . ?
C7 C8 C9 C10 -1.1(8) . . . . ?
C8 C9 C10 C11 0.2(8) . . . . ?
C9 C10 C11 C6 1.0(7) . . . . ?
C9 C10 C11 C15 -177.8(5) . . . . ?
C7 C6 C11 C10 -1.3(7) . . . . ?
N3 C6 C11 C10 -172.9(4) . . . . ?
C7 C6 C11 C15 177.5(5) . . . . ?
N3 C6 C11 C15 5.9(7) . . . . ?
C8 C7 C12 C13 -100.8(6) . . . . ?
C6 C7 C12 C13 75.0(6) . . . . ?
C8 C7 C12 C14 23.4(7) . . . . ?
C6 C7 C12 C14 -160.7(5) . . . . ?
C10 C11 C15 C16 60.0(7) . . . . ?
C6 C11 C15 C16 -118.8(6) . . . . ?
C10 C11 C15 C17 -64.2(7) . . . . ?
C6 C11 C15 C17 117.0(6) . . . . ?
C25 C18 C19 C20 4.0(8) . . . . ?
Ir1 C18 C19 C20 -103.0(5) . . . . ?
C25 C18 C19 Ir1 107.0(5) . . . . ?
C18 C19 C20 C21 47.0(8) . . . . ?
Ir1 C19 C20 C21 -33.7(7) . . . . ?
C19 C20 C21 C22 29.6(8) . . . . ?
C20 C21 C22 C23 -94.1(7) . . . . ?
C20 C21 C22 Ir1 -11.6(7) . . . . ?
C21 C22 C23 C24 3.6(9) . . . . ?
Ir1 C22 C23 C24 -102.0(5) . . . . ?
C21 C22 C23 Ir1 105.5(5) . . . . ?
C22 C23 C24 C25 47.1(8) . . . . ?
Ir1 C23 C24 C25 -32.7(7) . . . . ?
C19 C18 C25 C24 -94.4(7) . . . . ?
Ir1 C18 C25 C24 -12.5(7) . . . . ?
C23 C24 C25 C18 30.0(8) . . . . ?
N4 C27 C28 N5 -0.6(7) . . . . ?
C36 C31 C32 C33 -0.1(9) . . . . ?
N6 C31 C32 C33 176.4(5) . . . . ?
C36 C31 C32 C37 -177.9(6) . . . . ?
N6 C31 C32 C37 -1.4(8) . . . . ?
C31 C32 C33 C34 0.9(9) . . . . ?
C37 C32 C33 C34 178.7(6) . . . . ?
C32 C33 C34 C35 -2.3(10) . . . . ?
C33 C34 C35 C36 3.1(10) . . . . ?
C34 C35 C36 C31 -2.3(9) . . . . ?
C34 C35 C36 C40 -178.7(6) . . . . ?
C32 C31 C36 C35 0.8(8) . . . . ?
N6 C31 C36 C35 -175.6(5) . . . . ?
C32 C31 C36 C40 177.1(5) . . . . ?
N6 C31 C36 C40 0.7(8) . . . . ?
C31 C32 C37 C38 84.9(7) . . . . ?
C33 C32 C37 C38 -92.9(8) . . . . ?
C31 C32 C37 C39 -147.7(7) . . . . ?
C33 C32 C37 C39 34.5(9) . . . . ?
C35 C36 C40 C41 64.9(8) . . . . ?
C31 C36 C40 C41 -111.3(7) . . . . ?
C35 C36 C40 C42 -58.9(7) . . . . ?
C31 C36 C40 C42 124.8(6) . . . . ?
C50 C43 C44 C45 5.1(9) . . . . ?
Ir2 C43 C44 C45 -102.2(6) . . . . ?
C50 C43 C44 Ir2 107.3(5) . . . . ?
C43 C44 C45 C46 45.6(8) . . . . ?
Ir2 C44 C45 C46 -34.8(7) . . . . ?
C44 C45 C46 C47 30.8(8) . . . . ?
C45 C46 C47 C48 -92.4(7) . . . . ?
C45 C46 C47 Ir2 -11.7(7) . . . . ?
C46 C47 C48 C49 1.2(8) . . . . ?
Ir2 C47 C48 C49 -103.0(5) . . . . ?
C46 C47 C48 Ir2 104.3(5) . . . . ?
C47 C48 C49 C50 49.0(7) . . . . ?
Ir2 C48 C49 C50 -33.5(6) . . . . ?
C48 C49 C50 C43 29.7(7) . . . . ?
C44 C43 C50 C49 -93.7(7) . . . . ?
Ir2 C43 C50 C49 -11.5(7) . . . . ?
N2 C1 N1 C2 -0.7(5) . . . . ?
Ir1 C1 N1 C2 171.9(3) . . . . ?
N2 C1 N1 Ir2 -176.7(3) . . . . ?
Ir1 C1 N1 Ir2 -4.0(5) . . . . ?
C3 C2 N1 C1 0.1(6) . . . . ?
C3 C2 N1 Ir2 175.1(4) . . . . ?
N1 C1 N2 C3 1.1(5) . . . . ?
Ir1 C1 N2 C3 -169.2(4) . . . . ?
N1 C1 N2 C4 -175.5(5) . . . . ?
Ir1 C1 N2 C4 14.2(8) . . . . ?
C2 C3 N2 C1 -1.0(6) . . . . ?
C2 C3 N2 C4 175.9(4) . . . . ?
N3 C4 N2 C1 -150.5(5) . . . . ?
C5 C4 N2 C1 32.7(8) . . . . ?
N3 C4 N2 C3 33.2(7) . . . . ?
C5 C4 N2 C3 -143.6(5) . . . . ?
N2 C4 N3 C6 -175.3(4) . . . . ?
C5 C4 N3 C6 1.1(9) . . . . ?
C11 C6 N3 C4 -95.1(6) . . . . ?
C7 C6 N3 C4 93.0(6) . . . . ?
N5 C26 N4 C27 -2.5(6) . . . . ?
Ir2 C26 N4 C27 167.2(4) . . . . ?
N5 C26 N4 Ir1 -175.0(3) . . . . ?
Ir2 C26 N4 Ir1 -5.3(5) . . . . ?
C28 C27 N4 C26 2.0(7) . . . . ?
C28 C27 N4 Ir1 172.6(4) . . . . ?
N4 C26 N5 C28 2.1(6) . . . . ?
Ir2 C26 N5 C28 -164.5(5) . . . . ?
N4 C26 N5 C29 -164.4(5) . . . . ?
Ir2 C26 N5 C29 29.0(9) . . . . ?
C27 C28 N5 C26 -1.0(7) . . . . ?
C27 C28 N5 C29 166.6(5) . . . . ?
N6 C29 N5 C26 -161.7(5) . . . . ?
C30 C29 N5 C26 24.1(8) . . . . ?
N6 C29 N5 C28 33.2(7) . . . . ?
C30 C29 N5 C28 -141.0(6) . . . . ?
N5 C29 N6 C31 -168.9(5) . . . . ?
C30 C29 N6 C31 4.5(9) . . . . ?
C32 C31 N6 C29 97.5(6) . . . . ?
C36 C31 N6 C29 -86.0(7) . . . . ?

_refine_diff_density_max         1.529
_refine_diff_density_min         -2.862
_refine_diff_density_rms         0.310

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
1 -0.004 0.500 1.000 628.5 318.3
_platon_squeeze_details          
;
 The residual electron density was assigned to four molecules of the
 diethyl ether solvent [318/2 = 159 e per asymmetric unit; four molecules
 of C4H10O would give 168e].
;

_shelxl_version_number           2013-4

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

data_pbfh140623
_database_code_depnum_ccdc_archive 'CCDC 1039714'
_audit_update_record             
;
2014-12-16 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H35 Ir N3, F6 P'
_chemical_formula_sum            'C25 H35 F6 Ir N3 P'
_chemical_formula_weight         714.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   10.2750(4)
_cell_length_b                   10.7121(4)
_cell_length_c                   13.6503(5)
_cell_angle_alpha                105.8340(10)
_cell_angle_beta                 110.0360(10)
_cell_angle_gamma                97.4030(10)
_cell_volume                     1316.23(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9776
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      30.96

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.195
_shelx_estimated_absorpt_T_min   0.490
_shelx_estimated_absorpt_T_max   0.681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6107
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  triumph
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21762
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.689
_diffrn_reflns_theta_max         30.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8346
_reflns_number_gt                7098
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_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)+(0.0433P)²+1.0622P] 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         8346
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1374(4) 0.9966(4) 0.2497(3) 0.0232(7) Uani 1 1 d . . . . .
C2 C -0.3787(4) 0.9565(5) 0.1713(4) 0.0393(10) Uani 1 1 d . . . . .
H2 H -0.4718 0.9716 0.1549 0.047 Uiso 1 1 calc R U . . .
C3 C -0.3468(4) 0.8427(5) 0.1294(4) 0.0341(9) Uani 1 1 d . . . . .
H3 H -0.4119 0.7610 0.0773 0.041 Uiso 1 1 calc R U . . .
C4 C -0.1064(3) 0.7882(4) 0.1575(3) 0.0223(7) Uani 1 1 d . . . . .
C5 C -0.1714(4) 0.6509(4) 0.0752(3) 0.0306(8) Uani 1 1 d . . . . .
H5A H -0.0959 0.6046 0.0719 0.046 Uiso 1 1 calc R U . . .
H5B H -0.2242 0.6559 0.0020 0.046 Uiso 1 1 calc R U . . .
H5C H -0.2370 0.6015 0.0973 0.046 Uiso 1 1 calc R U . . .
C6 C 0.1334(3) 0.7769(3) 0.1951(3) 0.0219(7) Uani 1 1 d . . . . .
C7 C 0.1943(4) 0.7116(4) 0.2693(3) 0.0256(7) Uani 1 1 d . . . . .
C8 C 0.2960(4) 0.6451(4) 0.2502(4) 0.0340(9) Uani 1 1 d . . . . .
H8 H 0.3385 0.5984 0.2978 0.041 Uiso 1 1 calc R U . . .
C9 C 0.3366(4) 0.6455(4) 0.1633(4) 0.0384(10) Uani 1 1 d . . . . .
H9 H 0.4056 0.5989 0.1518 0.046 Uiso 1 1 calc R U . . .
C10 C 0.2773(4) 0.7134(4) 0.0938(4) 0.0323(8) Uani 1 1 d . . . . .
H10 H 0.3069 0.7139 0.0351 0.039 Uiso 1 1 calc R U . . .
C11 C 0.1743(4) 0.7815(4) 0.1081(3) 0.0256(7) Uani 1 1 d . . . . .
C12 C 0.1465(4) 0.7097(4) 0.3631(3) 0.0299(8) Uani 1 1 d . . . . .
H12 H 0.1070 0.7898 0.3801 0.036 Uiso 1 1 calc R U . . .
C13 C 0.0270(5) 0.5864(5) 0.3289(4) 0.0423(10) Uani 1 1 d . . . . .
H13A H -0.0582 0.5893 0.2694 0.063 Uiso 1 1 calc R U . . .
H13B H 0.0044 0.5849 0.3928 0.063 Uiso 1 1 calc R U . . .
H13C H 0.0579 0.5055 0.3024 0.063 Uiso 1 1 calc R U . . .
C14 C 0.2701(5) 0.7212(5) 0.4699(4) 0.0434(11) Uani 1 1 d . . . . .
H14A H 0.3076 0.6412 0.4576 0.065 Uiso 1 1 calc R U . . .
H14B H 0.2358 0.7289 0.5295 0.065 Uiso 1 1 calc R U . . .
H14C H 0.3462 0.8007 0.4909 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1091(4) 0.8547(5) 0.0290(4) 0.0366(10) Uani 1 1 d . . . . .
H15 H 0.0410 0.8992 0.0546 0.044 Uiso 1 1 calc R U . . .
C16 C 0.0247(6) 0.7583(7) -0.0895(4) 0.0606(16) Uani 1 1 d . . . . .
H16A H 0.0903 0.7189 -0.1190 0.091 Uiso 1 1 calc R U . . .
H16B H -0.0247 0.8071 -0.1359 0.091 Uiso 1 1 calc R U . . .
H16C H -0.0457 0.6870 -0.0898 0.091 Uiso 1 1 calc R U . . .
C17 C 0.2228(5) 0.9637(5) 0.0307(4) 0.0413(10) Uani 1 1 d . . . . .
H17A H 0.2764 1.0254 0.1069 0.062 Uiso 1 1 calc R U . . .
H17B H 0.1763 1.0132 -0.0163 0.062 Uiso 1 1 calc R U . . .
H17C H 0.2884 0.9223 0.0025 0.062 Uiso 1 1 calc R U . . .
C18 C 0.0865(5) 1.1881(4) 0.4704(4) 0.0375(9) Uani 1 1 d . . . . .
H18 H -0.0066 1.1404 0.4558 0.045 Uiso 1 1 calc R U . . .
C19 C 0.2082(6) 1.1877(8) 0.5711(4) 0.0681(13) Uani 1 1 d . . . . .
H19A H 0.2515 1.2813 0.6221 0.082 Uiso 1 1 calc R U . . .
H19B H 0.1680 1.1379 0.6097 0.082 Uiso 1 1 calc R U . . .
C20 C 0.3216(7) 1.1301(8) 0.5511(4) 0.0681(13) Uani 1 1 d . . . . .
H20A H 0.3421 1.0688 0.5940 0.082 Uiso 1 1 calc R U . . .
H20B H 0.4088 1.2037 0.5819 0.082 Uiso 1 1 calc R U . . .
C21 C 0.2970(4) 1.0546(4) 0.4335(4) 0.0340(9) Uani 1 1 d . . . . .
H21 H 0.2755 0.9596 0.4099 0.041 Uiso 1 1 calc R U . . .
C22 C 0.3039(4) 1.1148(5) 0.3587(4) 0.0412(10) Uani 1 1 d . . . . .
H22 H 0.2887 1.0561 0.2875 0.049 Uiso 1 1 calc R U . . .
C23 C 0.3315(6) 1.2580(6) 0.3731(7) 0.0744(15) Uani 1 1 d . . . . .
H23A H 0.4308 1.3007 0.4280 0.089 Uiso 1 1 calc R U . . .
H23B H 0.3273 1.2664 0.3018 0.089 Uiso 1 1 calc R U . . .
C24 C 0.2382(6) 1.3360(6) 0.4086(7) 0.0744(15) Uani 1 1 d . . . . .
H24A H 0.2159 1.3959 0.3646 0.089 Uiso 1 1 calc R U . . .
H24B H 0.2912 1.3931 0.4873 0.089 Uiso 1 1 calc R U . . .
C25 C 0.0996(4) 1.2532(4) 0.3967(4) 0.0349(9) Uani 1 1 d . . . . .
H25 H 0.0155 1.2445 0.3350 0.042 Uiso 1 1 calc R U . . .
N1 N -0.2500(3) 1.0495(4) 0.2439(3) 0.0333(8) Uani 1 1 d . . . . .
N2 N -0.1977(3) 0.8681(3) 0.1780(2) 0.0231(6) Uani 1 1 d . . . . .
N3 N 0.0278(3) 0.8473(3) 0.2128(2) 0.0194(5) Uani 1 1 d . . . . .
F1 F 0.4078(5) 0.7677(5) 0.8929(3) 0.0890(14) Uani 1 1 d . . . . .
F2 F 0.5735(4) 0.6693(5) 0.8537(3) 0.0835(12) Uani 1 1 d . . . . .
F3 F 0.4156(5) 0.5494(4) 0.6878(4) 0.0919(13) Uani 1 1 d . . . . .
F4 F 0.2466(4) 0.6495(5) 0.7232(4) 0.0991(15) Uani 1 1 d . . . . .
F5 F 0.3695(7) 0.5412(6) 0.8342(7) 0.152(3) Uani 1 1 d . . . . .
F6 F 0.4482(4) 0.7708(4) 0.7447(3) 0.0664(9) Uani 1 1 d . . . . .
P1 P 0.40937(12) 0.65411(13) 0.79097(11) 0.0394(3) Uani 1 1 d . . . . .
Ir1 Ir 0.07414(2) 1.04395(2) 0.32417(2) 0.02116(5) Uani 1 1 d . . . . .
H1N H -0.237(5) 1.131(5) 0.278(4) 0.040(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(4) . ?
C1 N2 1.366(5) . ?
C1 Ir1 1.984(3) . ?
C2 C3 1.332(6) . ?
C2 N1 1.395(6) . ?
C2 H2 0.9500 . ?
C3 N2 1.400(4) . ?
C3 H3 0.9500 . ?
C4 N3 1.293(4) . ?
C4 N2 1.395(4) . ?
C4 C5 1.485(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.400(5) . ?
C6 C7 1.404(5) . ?
C6 N3 1.448(4) . ?
C7 C8 1.395(5) . ?
C7 C12 1.524(6) . ?
C8 C9 1.386(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(5) . ?
C10 H10 0.9500 . ?
C11 C15 1.526(5) . ?
C12 C13 1.524(6) . ?
C12 C14 1.532(5) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.528(7) . ?
C15 C17 1.532(6) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C25 1.403(7) . ?
C18 C19 1.510(7) . ?
C18 Ir1 2.116(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.458(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.501(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.365(7) . ?
C21 Ir1 2.232(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.468(7) . ?
C22 Ir1 2.225(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.468(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.509(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 Ir1 2.129(4) . ?
C25 H25 0.9500 . ?
N1 H1N 0.84(5) . ?
N3 Ir1 2.115(3) . ?
F1 P1 1.586(4) . ?
F2 P1 1.571(3) . ?
F3 P1 1.569(4) . ?
F4 P1 1.597(4) . ?
F5 P1 1.551(4) . ?
F6 P1 1.611(4) . ?

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 C1 N2 103.5(3) . . ?
N1 C1 Ir1 141.3(3) . . ?
N2 C1 Ir1 115.1(2) . . ?
C3 C2 N1 107.2(3) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C2 C3 N2 105.8(4) . . ?
C2 C3 H3 127.1 . . ?
N2 C3 H3 127.1 . . ?
N3 C4 N2 113.9(3) . . ?
N3 C4 C5 128.0(3) . . ?
N2 C4 C5 118.0(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 123.1(3) . . ?
C11 C6 N3 118.7(3) . . ?
C7 C6 N3 118.1(3) . . ?
C8 C7 C6 116.7(4) . . ?
C8 C7 C12 122.2(3) . . ?
C6 C7 C12 121.1(3) . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C6 117.3(3) . . ?
C10 C11 C15 120.1(4) . . ?
C6 C11 C15 122.7(3) . . ?
C7 C12 C13 111.8(3) . . ?
C7 C12 C14 112.8(3) . . ?
C13 C12 C14 110.3(3) . . ?
C7 C12 H12 107.2 . . ?
C13 C12 H12 107.2 . . ?
C14 C12 H12 107.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 C16 111.8(4) . . ?
C11 C15 C17 111.8(3) . . ?
C16 C15 C17 109.8(4) . . ?
C11 C15 H15 107.8 . . ?
C16 C15 H15 107.8 . . ?
C17 C15 H15 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C25 C18 C19 125.3(5) . . ?
C25 C18 Ir1 71.2(2) . . ?
C19 C18 Ir1 111.2(3) . . ?
C25 C18 H18 117.4 . . ?
C19 C18 H18 117.4 . . ?
Ir1 C18 H18 87.6 . . ?
C20 C19 C18 116.6(4) . . ?
C20 C19 H19A 108.1 . . ?
C18 C19 H19A 108.1 . . ?
C20 C19 H19B 108.1 . . ?
C18 C19 H19B 108.1 . . ?
H19A C19 H19B 107.3 . . ?
C19 C20 C21 118.1(4) . . ?
C19 C20 H20A 107.8 . . ?
C21 C20 H20A 107.8 . . ?
C19 C20 H20B 107.8 . . ?
C21 C20 H20B 107.8 . . ?
H20A C20 H20B 107.1 . . ?
C22 C21 C20 123.6(5) . . ?
C22 C21 Ir1 71.9(2) . . ?
C20 C21 Ir1 108.4(3) . . ?
C22 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?
Ir1 C21 H21 89.7 . . ?
C21 C22 C23 128.9(6) . . ?
C21 C22 Ir1 72.5(2) . . ?
C23 C22 Ir1 107.7(3) . . ?
C21 C22 H22 115.5 . . ?
C23 C22 H22 115.5 . . ?
Ir1 C22 H22 89.9 . . ?
C24 C23 C22 118.6(5) . . ?
C24 C23 H23A 107.7 . . ?
C22 C23 H23A 107.7 . . ?
C24 C23 H23B 107.7 . . ?
C22 C23 H23B 107.7 . . ?
H23A C23 H23B 107.1 . . ?
C23 C24 C25 114.7(5) . . ?
C23 C24 H24A 108.6 . . ?
C25 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
C25 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C18 C25 C24 124.5(5) . . ?
C18 C25 Ir1 70.2(2) . . ?
C24 C25 Ir1 112.8(3) . . ?
C18 C25 H25 117.7 . . ?
C24 C25 H25 117.7 . . ?
Ir1 C25 H25 87.0 . . ?
C1 N1 C2 111.8(4) . . ?
C1 N1 H1N 120(3) . . ?
C2 N1 H1N 128(3) . . ?
C1 N2 C4 117.9(3) . . ?
C1 N2 C3 111.6(3) . . ?
C4 N2 C3 130.3(3) . . ?
C4 N3 C6 119.2(3) . . ?
C4 N3 Ir1 115.7(2) . . ?
C6 N3 Ir1 125.1(2) . . ?
F5 P1 F3 91.0(3) . . ?
F5 P1 F2 91.7(3) . . ?
F3 P1 F2 88.1(2) . . ?
F5 P1 F1 92.8(3) . . ?
F3 P1 F1 176.1(3) . . ?
F2 P1 F1 91.1(2) . . ?
F5 P1 F4 93.6(3) . . ?
F3 P1 F4 91.8(3) . . ?
F2 P1 F4 174.7(3) . . ?
F1 P1 F4 88.6(2) . . ?
F5 P1 F6 179.1(3) . . ?
F3 P1 F6 88.8(2) . . ?
F2 P1 F6 89.1(2) . . ?
F1 P1 F6 87.4(2) . . ?
F4 P1 F6 85.6(2) . . ?
C1 Ir1 N3 77.15(13) . . ?
C1 Ir1 C18 95.60(16) . . ?
N3 Ir1 C18 154.46(16) . . ?
C1 Ir1 C25 96.52(15) . . ?
N3 Ir1 C25 164.84(14) . . ?
C18 Ir1 C25 38.61(18) . . ?
C1 Ir1 C22 161.24(17) . . ?
N3 Ir1 C22 100.53(15) . . ?
C18 Ir1 C22 93.85(19) . . ?
C25 Ir1 C22 80.97(17) . . ?
C1 Ir1 C21 162.50(16) . . ?
N3 Ir1 C21 97.65(13) . . ?
C18 Ir1 C21 81.89(17) . . ?
C25 Ir1 C21 92.26(16) . . ?
C22 Ir1 C21 35.65(17) . . ?

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 C2 C3 N2 0.3(5) . . . . ?
C11 C6 C7 C8 -2.4(5) . . . . ?
N3 C6 C7 C8 -179.8(3) . . . . ?
C11 C6 C7 C12 179.8(3) . . . . ?
N3 C6 C7 C12 2.5(5) . . . . ?
C6 C7 C8 C9 1.1(6) . . . . ?
C12 C7 C8 C9 178.8(4) . . . . ?
C7 C8 C9 C10 0.5(7) . . . . ?
C8 C9 C10 C11 -0.8(7) . . . . ?
C9 C10 C11 C6 -0.5(6) . . . . ?
C9 C10 C11 C15 -179.4(4) . . . . ?
C7 C6 C11 C10 2.2(5) . . . . ?
N3 C6 C11 C10 179.5(3) . . . . ?
C7 C6 C11 C15 -179.0(4) . . . . ?
N3 C6 C11 C15 -1.7(5) . . . . ?
C8 C7 C12 C13 -85.3(4) . . . . ?
C6 C7 C12 C13 92.3(4) . . . . ?
C8 C7 C12 C14 39.7(5) . . . . ?
C6 C7 C12 C14 -142.7(4) . . . . ?
C10 C11 C15 C16 63.8(5) . . . . ?
C6 C11 C15 C16 -115.1(4) . . . . ?
C10 C11 C15 C17 -59.8(5) . . . . ?
C6 C11 C15 C17 121.4(4) . . . . ?
C25 C18 C19 C20 -60.6(8) . . . . ?
Ir1 C18 C19 C20 20.8(8) . . . . ?
C18 C19 C20 C21 -10.8(10) . . . . ?
C19 C20 C21 C22 75.9(8) . . . . ?
C19 C20 C21 Ir1 -4.2(8) . . . . ?
C20 C21 C22 C23 -1.6(7) . . . . ?
Ir1 C21 C22 C23 98.8(5) . . . . ?
C20 C21 C22 Ir1 -100.4(4) . . . . ?
C21 C22 C23 C24 -56.6(9) . . . . ?
Ir1 C22 C23 C24 24.8(8) . . . . ?
C22 C23 C24 C25 -15.9(10) . . . . ?
C19 C18 C25 C24 -1.5(7) . . . . ?
Ir1 C18 C25 C24 -104.6(5) . . . . ?
C19 C18 C25 Ir1 103.1(5) . . . . ?
C23 C24 C25 C18 78.4(8) . . . . ?
C23 C24 C25 Ir1 -2.6(8) . . . . ?
N2 C1 N1 C2 0.7(5) . . . . ?
Ir1 C1 N1 C2 -179.7(4) . . . . ?
C3 C2 N1 C1 -0.7(5) . . . . ?
N1 C1 N2 C4 174.5(3) . . . . ?
Ir1 C1 N2 C4 -5.2(4) . . . . ?
N1 C1 N2 C3 -0.5(4) . . . . ?
Ir1 C1 N2 C3 179.8(3) . . . . ?
N3 C4 N2 C1 1.5(5) . . . . ?
C5 C4 N2 C1 -176.9(3) . . . . ?
N3 C4 N2 C3 175.4(4) . . . . ?
C5 C4 N2 C3 -2.9(6) . . . . ?
C2 C3 N2 C1 0.1(5) . . . . ?
C2 C3 N2 C4 -174.1(4) . . . . ?
N2 C4 N3 C6 -177.3(3) . . . . ?
C5 C4 N3 C6 0.9(6) . . . . ?
N2 C4 N3 Ir1 2.7(4) . . . . ?
C5 C4 N3 Ir1 -179.1(3) . . . . ?
C11 C6 N3 C4 85.6(4) . . . . ?
C7 C6 N3 C4 -97.0(4) . . . . ?
C11 C6 N3 Ir1 -94.4(3) . . . . ?
C7 C6 N3 Ir1 83.1(4) . . . . ?

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
N1 H1N F4 0.84(5) 2.37(5) 3.125(6) 150(5) 2_576
N1 H1N F6 0.84(5) 2.49(5) 2.990(4) 119(4) 2_576

_refine_diff_density_max         2.227
_refine_diff_density_min         -2.105
_refine_diff_density_rms         0.150

_shelxl_version_number           2013-4

