# Electronic Supplementary Material (ESI) for ChemComm.
# 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_Amn135_0m
_database_code_depnum_ccdc_archive 'CCDC 1015124'
_audit_update_record             
;
2014-07-21 deposited with the CCDC.
2015-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'[(Bis(2-phenyl-pyridine))(1-Pyrazin-2-yl-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine)]iridium(III) hexafluorophosphate dichloromethane'
_chemical_name_common            ?
_chemical_melting_point          'not determined'
_chemical_formula_moiety         'C33 H31 Ir N7, F6 P, C H2 Cl2'
_chemical_formula_sum            'C34 H33 Cl2 F6 Ir N7 P'
_chemical_formula_weight         947.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0600 0.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2600 0.3350 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -5.4390 5.4710 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.9180(12)
_cell_length_b                   16.0878(17)
_cell_length_c                   39.160(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6878.4(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9449
_cell_measurement_theta_min      4.78
_cell_measurement_theta_max      60.04

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_F_000             3728
_exptl_transmission_factor_min   0.5796
_exptl_transmission_factor_max   0.7517
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    6.855
_shelx_estimated_absorpt_T_min   0.493
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            110188
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         1.963
_diffrn_reflns_theta_max         60.085
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7694
_reflns_number_gt                6939
_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)+192.1591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7694
_refine_ls_number_parameters     460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.1875
_refine_ls_wR_factor_gt          0.1849
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_restrained_S_all      1.241
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F5 F 0.4490(9) 0.8565(5) 0.3888(2) 0.066(2) Uani 1 1 d . . . . .
Ir1 Ir 0.02789(4) 0.66221(3) 0.34286(2) 0.02631(14) Uani 1 1 d . . . . .
Cl1 Cl 0.7938(5) 0.6195(3) 0.49175(15) 0.0917(15) Uani 1 1 d . . . . .
Cl2 Cl 0.5782(5) 0.5358(3) 0.46619(15) 0.0955(16) Uani 1 1 d . . . . .
P1 P 0.4429(3) 0.7935(2) 0.42031(9) 0.0428(7) Uani 1 1 d . . . . .
F1 F 0.4830(10) 0.8662(6) 0.4446(2) 0.082(3) Uani 1 1 d . . . . .
F2 F 0.4385(9) 0.7313(6) 0.4517(2) 0.071(3) Uani 1 1 d . . . . .
F3 F 0.3035(8) 0.8143(9) 0.4245(3) 0.105(4) Uani 1 1 d . . . . .
F4 F 0.4094(10) 0.7207(5) 0.3943(2) 0.080(3) Uani 1 1 d . . . . .
F6 F 0.5848(8) 0.7716(6) 0.4153(3) 0.077(3) Uani 1 1 d . . . . .
N1 N 0.1669(8) 0.7267(5) 0.3187(2) 0.0292(18) Uani 1 1 d . . . . .
N2 N -0.1187(7) 0.5968(5) 0.3609(2) 0.0249(17) Uani 1 1 d . . . . .
N3 N 0.1696(7) 0.5809(5) 0.3615(2) 0.0300(19) Uani 1 1 d . . . . .
N4 N 0.3742(10) 0.4894(6) 0.3819(3) 0.050(3) Uani 1 1 d . . . . .
N5 N 0.1158(9) 0.6002(6) 0.4199(2) 0.035(2) Uani 1 1 d . . . . .
N6 N 0.0559(10) 0.7126(6) 0.4518(3) 0.043(2) Uani 1 1 d . . . . .
N7 N 0.0473(8) 0.7202(5) 0.3916(2) 0.0306(19) Uani 1 1 d . . . . .
C1 C 0.0163(9) 0.6110(6) 0.2965(3) 0.029(2) Uani 1 1 d . . . . .
C2 C 0.0993(9) 0.6433(6) 0.2722(3) 0.031(2) Uani 1 1 d . . . . .
C3 C 0.1034(10) 0.6147(7) 0.2380(3) 0.035(2) Uani 1 1 d . . . . .
H3 H 0.1614 0.6369 0.2224 0.042 Uiso 1 1 calc R U . . .
C4 C 0.0227(11) 0.5543(8) 0.2277(3) 0.044(3) Uani 1 1 d . . . . .
H4 H 0.0248 0.5342 0.2049 0.053 Uiso 1 1 calc R U . . .
C5 C -0.0619(11) 0.5228(7) 0.2506(3) 0.040(3) Uani 1 1 d . . . . .
H5 H -0.1187 0.4819 0.2432 0.048 Uiso 1 1 calc R U . . .
C6 C -0.0653(10) 0.5500(7) 0.2843(3) 0.034(2) Uani 1 1 d . . . . .
H6 H -0.1241 0.5268 0.2994 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1850(9) 0.7072(7) 0.2853(3) 0.033(2) Uani 1 1 d . . . . .
C8 C 0.2395(10) 0.7819(7) 0.3339(3) 0.034(2) Uani 1 1 d . . . . .
H8 H 0.2267 0.7949 0.3573 0.041 Uiso 1 1 calc R U . . .
C9 C 0.3336(11) 0.8209(7) 0.3163(3) 0.040(3) Uani 1 1 d . . . . .
H9 H 0.3843 0.8605 0.3274 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3527(11) 0.8014(8) 0.2824(3) 0.045(3) Uani 1 1 d . . . . .
H10 H 0.4166 0.8278 0.2700 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2790(10) 0.7439(8) 0.2666(3) 0.040(3) Uani 1 1 d . . . . .
H11 H 0.2920 0.7295 0.2434 0.048 Uiso 1 1 calc R U . . .
C12 C -0.1073(9) 0.7397(6) 0.3285(3) 0.026(2) Uani 1 1 d . . . . .
C13 C -0.2260(9) 0.7148(6) 0.3389(3) 0.029(2) Uani 1 1 d . . . . .
C14 C -0.3290(10) 0.7632(6) 0.3323(3) 0.033(2) Uani 1 1 d . . . . .
H14 H -0.4077 0.7449 0.3394 0.040 Uiso 1 1 calc R U . . .
C15 C -0.3166(10) 0.8377(7) 0.3153(3) 0.037(2) Uani 1 1 d . . . . .
H15 H -0.3865 0.8712 0.3110 0.044 Uiso 1 1 calc R U . . .
C16 C -0.2013(9) 0.8639(7) 0.3044(3) 0.033(2) Uani 1 1 d . . . . .
H16 H -0.1929 0.9149 0.2924 0.040 Uiso 1 1 calc R U . . .
C17 C -0.0983(9) 0.8153(6) 0.3111(3) 0.030(2) Uani 1 1 d . . . . .
H17 H -0.0202 0.8341 0.3037 0.036 Uiso 1 1 calc R U . . .
C18 C -0.2312(9) 0.6328(6) 0.3559(3) 0.028(2) Uani 1 1 d . . . . .
C19 C -0.1127(10) 0.5204(6) 0.3747(3) 0.032(2) Uani 1 1 d . . . . .
H19 H -0.0343 0.4964 0.3784 0.038 Uiso 1 1 calc R U . . .
C20 C -0.2146(10) 0.4753(7) 0.3837(3) 0.035(2) Uani 1 1 d . . . . .
H20 H -0.2071 0.4211 0.3930 0.043 Uiso 1 1 calc R U . . .
C21 C -0.3292(10) 0.5115(7) 0.3787(3) 0.038(2) Uani 1 1 d . . . . .
H21 H -0.4017 0.4823 0.3846 0.045 Uiso 1 1 calc R U . . .
C22 C -0.3364(9) 0.5908(7) 0.3649(3) 0.034(2) Uani 1 1 d . . . . .
H22 H -0.4140 0.6162 0.3616 0.041 Uiso 1 1 calc R U . . .
C23 C 0.1943(9) 0.5704(6) 0.3945(3) 0.031(2) Uani 1 1 d . . . . .
C24 C 0.3002(11) 0.5244(7) 0.4046(4) 0.044(3) Uani 1 1 d . . . . .
H24 H 0.3181 0.5187 0.4282 0.053 Uiso 1 1 calc R U . . .
C25 C 0.3433(9) 0.4965(8) 0.3494(4) 0.045(3) Uani 1 1 d . . . . .
H25 H 0.3899 0.4673 0.3328 0.054 Uiso 1 1 calc R U . . .
C26 C 0.2473(11) 0.5439(7) 0.3388(3) 0.042(3) Uani 1 1 d . . . . .
H26 H 0.2341 0.5513 0.3150 0.051 Uiso 1 1 calc R U . . .
C27 C 0.1101(14) 0.5553(8) 0.4524(3) 0.052(3) Uani 1 1 d . . . . .
H27A H 0.1457 0.4991 0.4496 0.062 Uiso 1 1 calc R U . . .
H27B H 0.0237 0.5490 0.4595 0.062 Uiso 1 1 calc R U . . .
C28 C 0.1797(17) 0.6020(9) 0.4790(4) 0.065(4) Uani 1 1 d . . . . .
H28A H 0.1756 0.5722 0.5011 0.078 Uiso 1 1 calc R U . . .
H28B H 0.2667 0.6071 0.4723 0.078 Uiso 1 1 calc R U . . .
C29 C 0.1235(16) 0.6861(9) 0.4824(4) 0.058(4) Uani 1 1 d . . . . .
H29A H 0.0668 0.6859 0.5021 0.070 Uiso 1 1 calc R U . . .
H29B H 0.1889 0.7270 0.4872 0.070 Uiso 1 1 calc R U . . .
C30 C -0.0128(14) 0.7912(8) 0.4580(3) 0.051(3) Uani 1 1 d . . . . .
H30A H 0.0444 0.8354 0.4654 0.061 Uiso 1 1 calc R U . . .
H30B H -0.0738 0.7826 0.4764 0.061 Uiso 1 1 calc R U . . .
C31 C -0.0772(12) 0.8172(7) 0.4254(3) 0.044(3) Uani 1 1 d . . . . .
H31A H -0.1053 0.8756 0.4271 0.053 Uiso 1 1 calc R U . . .
H31B H -0.1492 0.7813 0.4211 0.053 Uiso 1 1 calc R U . . .
C32 C 0.0155(11) 0.8082(7) 0.3964(3) 0.036(2) Uani 1 1 d . . . . .
H32A H -0.0197 0.8308 0.3751 0.044 Uiso 1 1 calc R U . . .
H32B H 0.0902 0.8404 0.4019 0.044 Uiso 1 1 calc R U . . .
C33 C 0.0729(10) 0.6825(7) 0.4199(3) 0.036(2) Uani 1 1 d . . . . .
C34 C 0.702(2) 0.6111(11) 0.4580(4) 0.103(8) Uani 1 1 d . . . . .
H34A H 0.7507 0.5927 0.4380 0.124 Uiso 1 1 calc R U . . .
H34B H 0.6665 0.6661 0.4526 0.124 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 P1 1.597(8) . ?
Ir1 C1 1.998(11) . ?
Ir1 C12 2.012(9) . ?
Ir1 N2 2.041(8) . ?
Ir1 N1 2.068(8) . ?
Ir1 N7 2.135(9) . ?
Ir1 N3 2.152(8) . ?
Cl1 C34 1.66(2) . ?
Cl2 C34 1.85(2) . ?
P1 F3 1.567(9) . ?
P1 F1 1.571(9) . ?
P1 F2 1.586(8) . ?
P1 F4 1.595(9) . ?
P1 F6 1.601(9) . ?
N1 C8 1.332(13) . ?
N1 C7 1.360(14) . ?
N2 C19 1.345(12) . ?
N2 C18 1.372(12) . ?
N3 C23 1.334(14) . ?
N3 C26 1.365(14) . ?
N4 C25 1.321(18) . ?
N4 C24 1.326(17) . ?
N5 C23 1.396(14) . ?
N5 C33 1.404(14) . ?
N5 C27 1.464(15) . ?
N6 C33 1.354(15) . ?
N6 C29 1.470(16) . ?
N6 C30 1.490(15) . ?
N7 C33 1.293(14) . ?
N7 C32 1.470(14) . ?
C1 C6 1.409(14) . ?
C1 C2 1.415(14) . ?
C2 C3 1.417(15) . ?
C2 C7 1.481(15) . ?
C3 C4 1.371(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C11 1.391(14) . ?
C8 C9 1.387(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(17) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.398(13) . ?
C12 C13 1.416(13) . ?
C13 C14 1.392(14) . ?
C13 C18 1.479(13) . ?
C14 C15 1.377(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(14) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C22 1.378(13) . ?
C19 C20 1.374(14) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(15) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.428(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.361(16) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.49(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.491(19) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.517(18) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.526(17) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ir1 C12 87.4(4) . . ?
C1 Ir1 N2 92.9(4) . . ?
C12 Ir1 N2 80.8(4) . . ?
C1 Ir1 N1 80.6(4) . . ?
C12 Ir1 N1 95.7(4) . . ?
N2 Ir1 N1 172.9(3) . . ?
C1 Ir1 N7 177.4(4) . . ?
C12 Ir1 N7 93.0(4) . . ?
N2 Ir1 N7 89.7(3) . . ?
N1 Ir1 N7 96.7(3) . . ?
C1 Ir1 N3 95.9(4) . . ?
C12 Ir1 N3 176.4(4) . . ?
N2 Ir1 N3 97.7(3) . . ?
N1 Ir1 N3 86.1(3) . . ?
N7 Ir1 N3 83.8(3) . . ?
F3 P1 F1 92.8(7) . . ?
F3 P1 F2 91.5(6) . . ?
F1 P1 F2 90.5(5) . . ?
F3 P1 F4 90.1(7) . . ?
F1 P1 F4 176.5(7) . . ?
F2 P1 F4 91.4(5) . . ?
F3 P1 F5 89.2(6) . . ?
F1 P1 F5 89.0(5) . . ?
F2 P1 F5 179.2(6) . . ?
F4 P1 F5 89.0(5) . . ?
F3 P1 F6 178.9(7) . . ?
F1 P1 F6 88.1(6) . . ?
F2 P1 F6 89.1(5) . . ?
F4 P1 F6 89.0(6) . . ?
F5 P1 F6 90.3(5) . . ?
C8 N1 C7 119.9(9) . . ?
C8 N1 Ir1 124.5(7) . . ?
C7 N1 Ir1 115.6(7) . . ?
C19 N2 C18 119.1(8) . . ?
C19 N2 Ir1 124.9(7) . . ?
C18 N2 Ir1 115.8(6) . . ?
C23 N3 C26 116.7(9) . . ?
C23 N3 Ir1 123.4(7) . . ?
C26 N3 Ir1 119.5(8) . . ?
C25 N4 C24 117.0(11) . . ?
C23 N5 C33 121.8(9) . . ?
C23 N5 C27 118.3(10) . . ?
C33 N5 C27 116.9(10) . . ?
C33 N6 C29 125.4(11) . . ?
C33 N6 C30 121.6(10) . . ?
C29 N6 C30 111.5(10) . . ?
C33 N7 C32 113.2(9) . . ?
C33 N7 Ir1 125.5(8) . . ?
C32 N7 Ir1 120.8(7) . . ?
C6 C1 C2 115.6(10) . . ?
C6 C1 Ir1 129.5(8) . . ?
C2 C1 Ir1 114.8(7) . . ?
C1 C2 C3 122.5(10) . . ?
C1 C2 C7 115.3(9) . . ?
C3 C2 C7 122.2(10) . . ?
C4 C3 C2 119.1(10) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.9(11) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.2(11) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 121.6(10) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C7 C11 120.9(10) . . ?
N1 C7 C2 113.7(9) . . ?
C11 C7 C2 125.4(11) . . ?
N1 C8 C9 121.3(11) . . ?
N1 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.2(11) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 119.8(11) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C7 118.9(11) . . ?
C10 C11 H11 120.6 . . ?
C7 C11 H11 120.6 . . ?
C17 C12 C13 116.8(9) . . ?
C17 C12 Ir1 128.6(8) . . ?
C13 C12 Ir1 114.6(7) . . ?
C14 C13 C12 121.9(9) . . ?
C14 C13 C18 123.5(9) . . ?
C12 C13 C18 114.6(9) . . ?
C15 C14 C13 119.8(10) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.0(10) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.1(10) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 121.5(10) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
N2 C18 C22 120.2(9) . . ?
N2 C18 C13 114.0(8) . . ?
C22 C18 C13 125.8(9) . . ?
N2 C19 C20 123.1(10) . . ?
N2 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C19 C20 C21 118.1(10) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C22 C21 C20 119.3(10) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C18 C22 C21 120.3(10) . . ?
C18 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
N3 C23 N5 121.5(9) . . ?
N3 C23 C24 119.9(11) . . ?
N5 C23 C24 118.5(11) . . ?
N4 C24 C23 121.8(12) . . ?
N4 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
N4 C25 C26 122.6(12) . . ?
N4 C25 H25 118.7 . . ?
C26 C25 H25 118.7 . . ?
C25 C26 N3 121.7(12) . . ?
C25 C26 H26 119.2 . . ?
N3 C26 H26 119.2 . . ?
N5 C27 C28 109.7(11) . . ?
N5 C27 H27A 109.7 . . ?
C28 C27 H27A 109.7 . . ?
N5 C27 H27B 109.7 . . ?
C28 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C29 C28 C27 108.0(12) . . ?
C29 C28 H28A 110.1 . . ?
C27 C28 H28A 110.1 . . ?
C29 C28 H28B 110.1 . . ?
C27 C28 H28B 110.1 . . ?
H28A C28 H28B 108.4 . . ?
N6 C29 C28 113.5(11) . . ?
N6 C29 H29A 108.9 . . ?
C28 C29 H29A 108.9 . . ?
N6 C29 H29B 108.9 . . ?
C28 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
N6 C30 C31 109.3(10) . . ?
N6 C30 H30A 109.8 . . ?
C31 C30 H30A 109.8 . . ?
N6 C30 H30B 109.8 . . ?
C31 C30 H30B 109.8 . . ?
H30A C30 H30B 108.3 . . ?
C30 C31 C32 107.0(10) . . ?
C30 C31 H31A 110.3 . . ?
C32 C31 H31A 110.3 . . ?
C30 C31 H31B 110.3 . . ?
C32 C31 H31B 110.3 . . ?
H31A C31 H31B 108.6 . . ?
N7 C32 C31 110.1(9) . . ?
N7 C32 H32A 109.6 . . ?
C31 C32 H32A 109.6 . . ?
N7 C32 H32B 109.6 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 108.2 . . ?
N7 C33 N6 126.3(11) . . ?
N7 C33 N5 121.1(11) . . ?
N6 C33 N5 112.5(10) . . ?
Cl1 C34 Cl2 110.8(10) . . ?
Cl1 C34 H34A 109.5 . . ?
Cl2 C34 H34A 109.5 . . ?
Cl1 C34 H34B 109.5 . . ?
Cl2 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.9(15) . . . . ?
Ir1 C1 C2 C3 -179.6(8) . . . . ?
C6 C1 C2 C7 -179.8(9) . . . . ?
Ir1 C1 C2 C7 2.5(12) . . . . ?
C1 C2 C3 C4 1.2(16) . . . . ?
C7 C2 C3 C4 178.9(10) . . . . ?
C2 C3 C4 C5 0.5(17) . . . . ?
C3 C4 C5 C6 -1.3(18) . . . . ?
C4 C5 C6 C1 0.4(18) . . . . ?
C2 C1 C6 C5 1.1(15) . . . . ?
Ir1 C1 C6 C5 178.4(9) . . . . ?
C8 N1 C7 C11 0.2(16) . . . . ?
Ir1 N1 C7 C11 -177.4(8) . . . . ?
C8 N1 C7 C2 178.4(9) . . . . ?
Ir1 N1 C7 C2 0.8(11) . . . . ?
C1 C2 C7 N1 -2.2(13) . . . . ?
C3 C2 C7 N1 179.9(10) . . . . ?
C1 C2 C7 C11 176.0(11) . . . . ?
C3 C2 C7 C11 -1.9(17) . . . . ?
C7 N1 C8 C9 0.5(16) . . . . ?
Ir1 N1 C8 C9 177.9(8) . . . . ?
N1 C8 C9 C10 -0.5(18) . . . . ?
C8 C9 C10 C11 -0.2(19) . . . . ?
C9 C10 C11 C7 0.9(19) . . . . ?
N1 C7 C11 C10 -0.9(17) . . . . ?
C2 C7 C11 C10 -178.9(11) . . . . ?
C17 C12 C13 C14 -0.1(16) . . . . ?
Ir1 C12 C13 C14 177.3(9) . . . . ?
C17 C12 C13 C18 177.5(9) . . . . ?
Ir1 C12 C13 C18 -5.1(12) . . . . ?
C12 C13 C14 C15 -0.4(17) . . . . ?
C18 C13 C14 C15 -177.8(10) . . . . ?
C13 C14 C15 C16 0.9(18) . . . . ?
C14 C15 C16 C17 -0.9(18) . . . . ?
C15 C16 C17 C12 0.5(17) . . . . ?
C13 C12 C17 C16 0.0(16) . . . . ?
Ir1 C12 C17 C16 -177.0(8) . . . . ?
C19 N2 C18 C22 -0.1(15) . . . . ?
Ir1 N2 C18 C22 175.3(8) . . . . ?
C19 N2 C18 C13 -177.0(9) . . . . ?
Ir1 N2 C18 C13 -1.6(11) . . . . ?
C14 C13 C18 N2 -178.1(10) . . . . ?
C12 C13 C18 N2 4.4(13) . . . . ?
C14 C13 C18 C22 5.2(18) . . . . ?
C12 C13 C18 C22 -172.4(11) . . . . ?
C18 N2 C19 C20 1.0(16) . . . . ?
Ir1 N2 C19 C20 -173.9(9) . . . . ?
N2 C19 C20 C21 -1.1(18) . . . . ?
C19 C20 C21 C22 0.2(18) . . . . ?
N2 C18 C22 C21 -0.8(17) . . . . ?
C13 C18 C22 C21 175.8(11) . . . . ?
C20 C21 C22 C18 0.7(18) . . . . ?
C26 N3 C23 N5 -175.0(9) . . . . ?
Ir1 N3 C23 N5 11.6(13) . . . . ?
C26 N3 C23 C24 1.9(14) . . . . ?
Ir1 N3 C23 C24 -171.5(7) . . . . ?
C33 N5 C23 N3 -50.2(14) . . . . ?
C27 N5 C23 N3 149.9(11) . . . . ?
C33 N5 C23 C24 132.8(11) . . . . ?
C27 N5 C23 C24 -27.1(15) . . . . ?
C25 N4 C24 C23 -2.3(17) . . . . ?
N3 C23 C24 N4 -1.8(16) . . . . ?
N5 C23 C24 N4 175.3(10) . . . . ?
C24 N4 C25 C26 6.3(18) . . . . ?
N4 C25 C26 N3 -6.3(19) . . . . ?
C23 N3 C26 C25 1.9(16) . . . . ?
Ir1 N3 C26 C25 175.5(9) . . . . ?
C23 N5 C27 C28 103.8(13) . . . . ?
C33 N5 C27 C28 -57.1(15) . . . . ?
N5 C27 C28 C29 59.3(17) . . . . ?
C33 N6 C29 C28 -22(2) . . . . ?
C30 N6 C29 C28 172.1(14) . . . . ?
C27 C28 C29 N6 -23.3(19) . . . . ?
C33 N6 C30 C31 11.4(17) . . . . ?
C29 N6 C30 C31 178.1(12) . . . . ?
N6 C30 C31 C32 -45.5(14) . . . . ?
C33 N7 C32 C31 -47.5(13) . . . . ?
Ir1 N7 C32 C31 125.1(9) . . . . ?
C30 C31 C32 N7 65.8(12) . . . . ?
C32 N7 C33 N6 10.0(16) . . . . ?
Ir1 N7 C33 N6 -162.2(9) . . . . ?
C32 N7 C33 N5 -174.3(9) . . . . ?
Ir1 N7 C33 N5 13.5(14) . . . . ?
C29 N6 C33 N7 -155.9(12) . . . . ?
C30 N6 C33 N7 8.9(19) . . . . ?
C29 N6 C33 N5 28.1(17) . . . . ?
C30 N6 C33 N5 -167.1(11) . . . . ?
C23 N5 C33 N7 36.2(15) . . . . ?
C27 N5 C33 N7 -163.6(11) . . . . ?
C23 N5 C33 N6 -147.5(10) . . . . ?
C27 N5 C33 N6 12.7(14) . . . . ?

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
C34 H34B F6 0.99 2.41 3.33(2) 154.7 .
C32 H32B N4 0.99 2.55 3.205(15) 123.4 8_665
C32 H32B F3 0.99 2.53 3.332(15) 138.5 .
C29 H29B Cl1 0.99 2.84 3.777(17) 157.5 4_466
C29 H29A F1 0.99 2.43 3.351(18) 155.2 4_466
C27 H27A F1 0.99 2.57 3.222(16) 123.7 8_655
C19 H19 N3 0.95 2.69 3.273(13) 120.2 .
C19 H19 F5 0.95 2.47 3.232(13) 137.3 8_655
C9 H9 F5 0.95 2.51 3.161(15) 126.0 .
C8 H8 N7 0.95 2.66 3.239(14) 119.8 .
C34 H34B F6 0.99 2.41 3.33(2) 154.7 .
C32 H32B N4 0.99 2.55 3.205(15) 123.4 8_665
C32 H32B F3 0.99 2.53 3.332(15) 138.5 .
C29 H29B Cl1 0.99 2.84 3.777(17) 157.5 4_466
C29 H29A F1 0.99 2.43 3.351(18) 155.2 4_466
C27 H27A F1 0.99 2.57 3.222(16) 123.7 8_655
C19 H19 N3 0.95 2.69 3.273(13) 120.2 .
C19 H19 F5 0.95 2.47 3.232(13) 137.3 8_655
C9 H9 F5 0.95 2.51 3.161(15) 126.0 .
C8 H8 N7 0.95 2.66 3.239(14) 119.8 .
C34 H34B F6 0.99 2.41 3.33(2) 154.7 .
C34 H34B F2 0.99 2.70 3.48(3) 135.5 .
C27 H27A F1 0.99 2.57 3.222(16) 123.7 8_655
C19 H19 F5 0.95 2.47 3.232(13) 137.3 8_655
C29 H29A F1 0.99 2.43 3.351(18) 155.2 4_466
C29 H29B Cl1 0.99 2.84 3.777(17) 157.5 4_466
C32 H32B F3 0.99 2.53 3.332(15) 138.5 .
C32 H32B N4 0.99 2.55 3.205(15) 123.4 8_665
C9 H9 F5 0.95 2.51 3.161(15) 126.0 .
C8 H8 N7 0.95 2.66 3.239(14) 119.8 .
C8 H8 N7 0.95 2.66 3.239(14) 119.8 .
C9 H9 F5 0.95 2.51 3.161(15) 126.0 .
C19 H19 F5 0.95 2.47 3.232(13) 137.3 8_655
C19 H19 N3 0.95 2.69 3.273(13) 120.2 .
C27 H27A F1 0.99 2.57 3.222(16) 123.7 8_655
C29 H29A F1 0.99 2.43 3.351(18) 155.2 4_466
C29 H29B Cl1 0.99 2.84 3.777(17) 157.5 4_466
C32 H32B F3 0.99 2.53 3.332(15) 138.5 .
C32 H32B N4 0.99 2.55 3.205(15) 123.4 8_665
C34 H34B F6 0.99 2.41 3.33(2) 154.7 .
C8 H8 N7 0.95 2.66 3.239(14) 119.8 .
C9 H9 F5 0.95 2.51 3.161(15) 126.0 .
C19 H19 F5 0.95 2.47 3.232(13) 137.3 8_655
C19 H19 N3 0.95 2.69 3.273(13) 120.2 .
C27 H27A F1 0.99 2.57 3.222(16) 123.7 8_655
C29 H29A F1 0.99 2.43 3.351(18) 155.2 4_466
C29 H29B Cl1 0.99 2.84 3.777(17) 157.5 4_466
C32 H32B F3 0.99 2.53 3.332(15) 138.5 .
C32 H32B N4 0.99 2.55 3.205(15) 123.4 8_665
C34 H34B F6 0.99 2.41 3.33(2) 154.7 .

_refine_diff_density_max         3.228
_refine_diff_density_min         -5.286
_refine_diff_density_rms         0.206

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Slow evaporation of dichloromethane solution of the title compound'
_chemical_compound_source        'Synthesized chemically by authors'
_exptl_crystal_preparation       Luminescent
