# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

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

data_Compound_2a
_database_code_depnum_ccdc_archive 'CCDC 1477775'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C20 H20 I N3 O2, 0.5(H2 O)'
_chemical_formula_sum            'C20 H21 I N3 O2.50'
_chemical_formula_weight         470.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   14.9781(5)
_cell_length_b                   14.9781(5)
_cell_length_c                   96.166(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     18683.8(14)
_cell_formula_units_Z            36
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      28.83

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             8460
_exptl_absorpt_coefficient_mu    1.563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            57842
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -137
_diffrn_reflns_limit_l_max       137
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6362
_reflns_number_gt                4712
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+83.8028P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6362
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.657
_refine_diff_density_min         -1.027
_refine_diff_density_rms         0.093

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
I1 I 0.17879(3) 0.333333 0.583333 0.06013(13) Uani 1 2 d S T P . .
I2 I 0.333333 0.666667 0.63944(2) 0.03228(9) Uani 1 3 d S T P . .
I3 I 0.59218(19) 0.3819(2) 0.61091(2) 0.0834(6) Uani 0.1667 1 d . . P A -1
O1 O 0.82952(18) 0.50040(19) 0.69080(2) 0.0449(5) Uani 1 1 d . . . . .
O2 O 0.5906(2) 0.5890(2) 0.70235(2) 0.0460(6) Uani 1 1 d . . . . .
O3 O 0.5408(10) 0.4037(9) 0.61431(12) 0.144(4) Uani 0.5 1 d . . P B -2
H3A H 0.524000 0.332864 0.613171 0.173 Uiso 0.5 1 d R U P B -2
H3B H 0.615613 0.437800 0.613873 0.173 Uiso 0.5 1 d R U P B -2
N1 N 0.55402(18) 0.59904(19) 0.63620(2) 0.0313(5) Uani 1 1 d . . . . .
N2 N 0.4767(2) 0.5771(3) 0.61662(3) 0.0447(7) Uani 1 1 d . . . . .
N3 N 0.7094(2) 0.5437(2) 0.69667(2) 0.0360(5) Uani 1 1 d . . . . .
C1 C 0.4684(3) 0.5373(3) 0.62916(3) 0.0389(6) Uani 1 1 d . . . . .
H1 H 0.411358 0.475435 0.632546 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5685(3) 0.6673(3) 0.61562(3) 0.0504(9) Uani 1 1 d . . . . .
H2 H 0.592862 0.711764 0.607771 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6181(3) 0.6816(3) 0.62783(3) 0.0433(7) Uani 1 1 d . . . . .
H3C H 0.684175 0.737355 0.630207 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5162(2) 0.6004(2) 0.66055(3) 0.0341(6) Uani 1 1 d . . . . .
H4 H 0.463631 0.615027 0.657947 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5731(2) 0.5865(2) 0.65054(3) 0.0287(5) Uani 1 1 d . . . . .
C6 C 0.6507(2) 0.5621(2) 0.65379(3) 0.0267(5) Uani 1 1 d . . . . .
C7 C 0.6702(2) 0.55616(19) 0.66818(3) 0.0250(5) Uani 1 1 d . . . . .
C8 C 0.6126(2) 0.5731(2) 0.67840(3) 0.0276(5) Uani 1 1 d . . . . .
C9 C 0.5357(2) 0.5930(2) 0.67467(3) 0.0341(6) Uani 1 1 d . . . . .
H9 H 0.495667 0.601716 0.681630 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7073(2) 0.5413(2) 0.64383(3) 0.0344(6) Uani 1 1 d . . . . .
H10 H 0.694499 0.543662 0.634198 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7807(3) 0.5176(3) 0.64798(3) 0.0415(7) Uani 1 1 d . . . . .
H11 H 0.818296 0.503893 0.641188 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8009(3) 0.5135(2) 0.66213(3) 0.0381(7) Uani 1 1 d . . . . .
H12 H 0.852786 0.498265 0.664844 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7460(2) 0.5315(2) 0.67208(3) 0.0279(5) Uani 1 1 d . . . . .
C14 C 0.7662(2) 0.5237(2) 0.68700(3) 0.0326(5) Uani 1 1 d . . . . .
C15 C 0.6351(2) 0.5694(2) 0.69325(3) 0.0333(6) Uani 1 1 d . . . . .
C16 C 0.3954(4) 0.5327(5) 0.60596(4) 0.0812(16) Uani 1 1 d . . . . .
H16A H 0.426235 0.556134 0.596740 0.122 Uiso 1 1 calc R U . . .
H16B H 0.345136 0.555189 0.607659 0.122 Uiso 1 1 calc R U . . .
H16C H 0.360788 0.457347 0.606390 0.122 Uiso 1 1 calc R U . . .
C17A C 0.7522(10) 0.5634(10) 0.71124(13) 0.032(2) Uani 0.3333 1 d . . P C -1
H17A H 0.826421 0.585241 0.711127 0.038 Uiso 0.3333 1 calc R U P C -1
H17B H 0.743577 0.618068 0.715749 0.038 Uiso 0.3333 1 calc R U P C -1
C18A C 0.6920(7) 0.4634(7) 0.71885(8) 0.0331(17) Uani 0.3333 1 d . . P C -1
H18A H 0.690380 0.407000 0.713288 0.040 Uiso 0.3333 1 calc R U P C -1
H18B H 0.620096 0.448067 0.720156 0.040 Uiso 0.3333 1 calc R U P C -1
C19A C 0.7408(9) 0.4692(9) 0.73294(10) 0.049(2) Uani 0.3333 1 d . . P C -1
H19A H 0.812559 0.484580 0.731542 0.058 Uiso 0.3333 1 calc R U P C -1
H19B H 0.743099 0.526487 0.738371 0.058 Uiso 0.3333 1 calc R U P C -1
C20A C 0.683(3) 0.3707(9) 0.74110(10) 0.055(3) Uani 0.3333 1 d . . P C -1
H20A H 0.716941 0.378226 0.750058 0.082 Uiso 0.3333 1 calc R U P C -1
H20B H 0.611941 0.355887 0.742691 0.082 Uiso 0.3333 1 calc R U P C -1
H20C H 0.681406 0.313978 0.735861 0.082 Uiso 0.3333 1 calc R U P C -1
C17B C 0.7165(5) 0.5236(5) 0.71185(7) 0.0363(14) Uani 0.6667 1 d . . P C -2
H17C H 0.647723 0.494421 0.716245 0.044 Uiso 0.6667 1 calc R U P C -2
H17D H 0.740535 0.473251 0.712913 0.044 Uiso 0.6667 1 calc R U P C -2
C18B C 0.7909(5) 0.6233(5) 0.71876(5) 0.0519(14) Uani 0.6667 1 d . . P C -2
H18C H 0.763058 0.670956 0.718406 0.062 Uiso 0.6667 1 calc R U P C -2
H18D H 0.857119 0.655770 0.713651 0.062 Uiso 0.6667 1 calc R U P C -2
C19B C 0.8094(6) 0.6064(6) 0.73375(6) 0.078(2) Uani 0.6667 1 d . . P C -2
H19C H 0.859739 0.582159 0.734547 0.093 Uiso 0.6667 1 d R U P C -2
H19D H 0.744475 0.556309 0.738413 0.093 Uiso 0.6667 1 d R U P C -2
C20B C 0.8799(12) 0.7085(10) 0.74092(10) 0.191(9) Uani 0.6667 1 d . . P C -2
H20D H 0.946558 0.743429 0.736120 0.287 Uiso 0.6667 1 calc R U P C -2
H20E H 0.890370 0.695708 0.750616 0.287 Uiso 0.6667 1 calc R U P C -2
H20F H 0.848341 0.752092 0.740642 0.287 Uiso 0.6667 1 calc R U P C -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.219(3) . ?
O2 C15 1.221(4) . ?
N1 C1 1.331(4) . ?
N1 C3 1.383(4) . ?
N1 C5 1.440(3) . ?
N2 C1 1.324(4) . ?
N2 C2 1.366(5) . ?
N2 C16 1.471(5) . ?
N3 C15 1.388(4) . ?
N3 C14 1.390(4) . ?
N3 C17B 1.505(7) . ?
N3 C17A 1.508(13) . ?
C2 C3 1.348(5) . ?
C4 C5 1.369(4) . ?
C4 C9 1.405(4) . ?
C5 C6 1.417(4) . ?
C6 C10 1.413(4) . ?
C6 C7 1.426(4) . ?
C7 C13 1.410(4) . ?
C7 C8 1.412(4) . ?
C8 C9 1.374(4) . ?
C8 C15 1.475(4) . ?
C10 C11 1.372(4) . ?
C11 C12 1.402(4) . ?
C12 C13 1.373(4) . ?
C13 C14 1.483(4) . ?
C17A C18A 1.497(14) . ?
C18A C19A 1.522(12) . ?
C19A C20A 1.505(17) . ?
C17B C18B 1.500(9) . ?
C18B C19B 1.513(7) . ?
C19B C20B 1.521(13) . ?

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 N1 C3 108.8(2) . . ?
C1 N1 C5 125.6(3) . . ?
C3 N1 C5 125.5(3) . . ?
C1 N2 C2 109.3(3) . . ?
C1 N2 C16 124.1(4) . . ?
C2 N2 C16 126.4(3) . . ?
C15 N3 C14 124.3(2) . . ?
C15 N3 C17B 115.5(4) . . ?
C14 N3 C17B 119.6(4) . . ?
C15 N3 C17A 119.1(6) . . ?
C14 N3 C17A 114.8(6) . . ?
N2 C1 N1 108.0(3) . . ?
C3 C2 N2 107.3(3) . . ?
C2 C3 N1 106.5(3) . . ?
C5 C4 C9 119.8(3) . . ?
C4 C5 C6 122.6(2) . . ?
C4 C5 N1 118.3(2) . . ?
C6 C5 N1 119.1(2) . . ?
C10 C6 C5 124.6(2) . . ?
C10 C6 C7 118.7(2) . . ?
C5 C6 C7 116.7(2) . . ?
C13 C7 C8 120.4(2) . . ?
C13 C7 C6 119.4(2) . . ?
C8 C7 C6 120.2(2) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 C15 119.6(2) . . ?
C7 C8 C15 119.7(2) . . ?
C8 C9 C4 120.0(3) . . ?
C11 C10 C6 120.4(3) . . ?
C10 C11 C12 120.8(3) . . ?
C13 C12 C11 120.3(3) . . ?
C12 C13 C7 120.4(3) . . ?
C12 C13 C14 119.5(3) . . ?
C7 C13 C14 120.1(2) . . ?
O1 C14 N3 120.5(3) . . ?
O1 C14 C13 122.1(3) . . ?
N3 C14 C13 117.3(2) . . ?
O2 C15 N3 120.5(3) . . ?
O2 C15 C8 121.5(3) . . ?
N3 C15 C8 118.0(2) . . ?
C18A C17A N3 105.9(8) . . ?
C17A C18A C19A 110.3(9) . . ?
C20A C19A C18A 112.5(12) . . ?
C18B C17B N3 108.8(5) . . ?
C17B C18B C19B 111.2(6) . . ?
C18B C19B C20B 110.9(7) . . ?

####################################################################### 
# 
# 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_Compound_5a
_database_code_depnum_ccdc_archive 'CCDC 1477777'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C46 H34 Ir N5 O2'
_chemical_formula_sum            'C46 H34 Ir N5 O2'
_chemical_formula_weight         880.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 '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                   13.5805(3)
_cell_length_b                   16.1341(4)
_cell_length_c                   21.2216(5)
_cell_angle_alpha                74.3020(10)
_cell_angle_beta                 89.5780(10)
_cell_angle_gamma                65.1590(10)
_cell_volume                     4032.06(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9444
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      66.71

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             1752
_exptl_absorpt_coefficient_mu    6.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.326
_exptl_absorpt_correction_T_max  0.782
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            56906
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.159
_diffrn_reflns_theta_max         66.710
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             14191
_reflns_number_gt                13333
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 The structure contains voids of severely disordered and partially evaporated
 solvent molecules, believed to be diethyl ether for the most part.
 Our attempts at modeling these molecules didn't yield satisfying results.
 PLATON-SQUEEZE was instead used to further refine the structure while
 accounting for the corresponding unassigned electron density.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+5.8003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         14191
_refine_ls_number_parameters     1000
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.068

# SQUEEZE RESULTS (Version = 160617)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material

_platon_squeeze_void_average_x   0.000
_platon_squeeze_void_average_y   0.000
_platon_squeeze_void_average_z   0.000
_platon_squeeze_void_volume      626
_platon_squeeze_void_count_electrons 128
_platon_squeeze_void_probe_radius 1.24

# Missing Reflections Below sin(th)/lambda = 0.25

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 0 1 2.179
-1 5 1 17.422

_platon_squeeze_details          
;
TITL shelx     P -1         R = 0.04
CELL   13.5805   16.1341   21.2216     74.30     89.58     65.16
SPGR P-1
C101 0.934 0.156 0.107 !       3.37 eA-3
C102 0.893 0.065 0.052 !       3.32 eA-3
C103 0.892 0.091 0.111 !       2.48 eA-3
C104 0.921 0.231 0.370 !       2.35 eA-3
C105 0.144 0.111 0.424 !       2.24 eA-3
C106 0.983 0.024 0.155 !       1.78 eA-3
C107 0.922 0.182 0.173 !       1.59 eA-3
Q108 0.778 0.341 0.355 !       1.38 eA-3
C109 0.011 0.059 0.201 !       1.38 eA-3
C110 0.097 0.963 0.251 !       1.37 eA-3
C111 0.984 0.101 0.221 !       1.34 eA-3
Q112 0.473 0.156 0.157 !       1.07 eA-3
Q113 0.451 0.096 0.204 !       0.93 eA-3
Q114 0.997 0.545 0.317 !       0.65 eA-3
Q115 0.269 0.710 0.487 !       0.65 eA-3
Q116 0.674 0.442 0.360 !       0.63 eA-3
C117 0.999 0.041 0.032 !       0.59 eA-3
Q118 0.215 0.246 0.424 !       0.58 eA-3
Q119 0.951 0.661 0.267 !       0.57 eA-3
C120 0.927 0.225 0.266 !       0.56 eA-3
Q121 0.626 0.344 0.468 !       0.55 eA-3
Q122 0.420 0.349 0.483 !       0.54 eA-3
Q123 0.408 0.240 0.134 !       0.53 eA-3
Q124 0.577 0.490 0.329 !       0.53 eA-3
Q125 0.234 0.277 0.471 !       0.52 eA-3
Q126 0.389 0.635 0.200 !       0.52 eA-3
Q127 0.310 0.585 0.450 !       0.52 eA-3
Q128 0.405 0.604 0.221 !       0.51 eA-3
Q129 0.042 0.611 0.283 !       0.51 eA-3
Q130 0.032 0.630 0.253 !       0.51 eA-3
Q131 0.015 0.653 0.229 !       0.51 eA-3
Q132 0.705 0.151 0.499 !       0.51 eA-3
Q133 0.358 0.140 0.218 !       0.50 eA-3
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.56803(2) 0.85066(2) 0.81653(2) 0.02800(4) Uani 1 1 d . . . . .
Ir2 Ir -0.02409(2) 0.61738(2) 0.28274(2) 0.02918(4) Uani 1 1 d . . . . .
O1 O 0.34376(18) 0.76450(16) 1.04014(12) 0.0468(5) Uani 1 1 d . . . . .
O2 O 0.5299(2) 0.45238(18) 1.15654(13) 0.0606(7) Uani 1 1 d . . . . .
O3 O 0.3557(2) 0.5806(2) 0.42747(19) 0.0865(11) Uani 1 1 d . . . . .
O4 O 0.2715(3) 0.8419(2) 0.49710(16) 0.0785(10) Uani 1 1 d . . . . .
N1 N 0.73760(19) 0.65295(17) 0.86733(12) 0.0318(5) Uani 1 1 d . . . . .
N2 N 0.8035(2) 0.71707(19) 0.78634(13) 0.0398(6) Uani 1 1 d . . . . .
N3 N 0.4417(2) 0.61016(19) 1.10052(13) 0.0403(6) Uani 1 1 d . . . . .
N4 N 0.47586(19) 0.82479(16) 0.75437(12) 0.0319(5) Uani 1 1 d . . . . .
N5 N 0.6390(2) 0.90449(18) 0.87017(12) 0.0350(5) Uani 1 1 d . . . . .
N6 N -0.1505(2) 0.78933(17) 0.32302(12) 0.0342(5) Uani 1 1 d . . . . .
N7 N -0.2731(2) 0.76183(18) 0.28105(13) 0.0375(6) Uani 1 1 d . . . . .
N8 N 0.3153(3) 0.7120(2) 0.46103(18) 0.0624(9) Uani 1 1 d . . . . .
N9 N -0.00384(18) 0.68712(16) 0.19053(11) 0.0296(5) Uani 1 1 d . . . . .
N10 N -0.0301(3) 0.52627(19) 0.37008(12) 0.0464(7) Uani 1 1 d . . . . .
C1 C 0.7132(2) 0.7349(2) 0.81656(14) 0.0340(6) Uani 1 1 d . . . . .
C2 C 0.8857(3) 0.6278(2) 0.81913(16) 0.0422(7) Uani 1 1 d . . . . .
H2 H 0.957555 0.600096 0.807492 0.051 Uiso 1 1 calc R U . . .
C3 C 0.8460(2) 0.5880(2) 0.86970(16) 0.0378(7) Uani 1 1 d . . . . .
H3 H 0.884084 0.527254 0.901324 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5696(2) 0.7439(2) 0.89972(13) 0.0291(6) Uani 1 1 d . . . . .
C5 C 0.6571(2) 0.6531(2) 0.91040(14) 0.0307(6) Uani 1 1 d . . . . .
C6 C 0.6637(2) 0.5689(2) 0.95757(14) 0.0317(6) Uani 1 1 d . . . . .
C7 C 0.5865(2) 0.5823(2) 1.00439(14) 0.0313(6) Uani 1 1 d . . . . .
C8 C 0.5019(2) 0.6746(2) 0.99752(14) 0.0318(6) Uani 1 1 d . . . . .
C9 C 0.4919(2) 0.7505(2) 0.94485(14) 0.0319(6) Uani 1 1 d . . . . .
H9 H 0.429918 0.810074 0.938570 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7355(3) 0.4731(2) 0.96077(16) 0.0388(7) Uani 1 1 d . . . . .
H10 H 0.784114 0.461477 0.928409 0.047 Uiso 1 1 calc R U . . .
C11 C 0.7360(3) 0.3973(2) 1.00944(17) 0.0437(8) Uani 1 1 d . . . . .
H11 H 0.784255 0.334084 1.010020 0.052 Uiso 1 1 calc R U . . .
C12 C 0.6666(3) 0.4116(2) 1.05819(17) 0.0425(7) Uani 1 1 d . . . . .
H12 H 0.670428 0.358574 1.093002 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5927(2) 0.5028(2) 1.05577(15) 0.0347(6) Uani 1 1 d . . . . .
C14 C 0.5207(3) 0.5174(2) 1.10827(17) 0.0420(7) Uani 1 1 d . . . . .
C15 C 0.4231(2) 0.6882(2) 1.04547(15) 0.0369(7) Uani 1 1 d . . . . .
C16 C 0.8150(3) 0.7804(3) 0.72637(19) 0.0579(10) Uani 1 1 d . . . . .
H16A H 0.889001 0.750762 0.714447 0.087 Uiso 1 1 calc R U . . .
H16B H 0.761525 0.791832 0.690515 0.087 Uiso 1 1 calc R U . . .
H16C H 0.802271 0.841334 0.733746 0.087 Uiso 1 1 calc R U . . .
C17 C 0.3712(3) 0.6292(3) 1.15259(19) 0.0564(9) Uani 1 1 d . . . . .
H17A H 0.376289 0.568154 1.182338 0.068 Uiso 1 1 calc R U . . .
H17B H 0.294211 0.669085 1.132592 0.068 Uiso 1 1 calc R U . . .
C18 C 0.4067(4) 0.6821(4) 1.1930(2) 0.0726(12) Uani 1 1 d . . . . .
H18A H 0.480502 0.638980 1.217218 0.087 Uiso 1 1 calc R U . . .
H18B H 0.410636 0.738794 1.162411 0.087 Uiso 1 1 calc R U . . .
C19 C 0.3289(5) 0.7128(5) 1.2406(3) 0.104(2) Uani 1 1 d . . . . .
H19A H 0.328320 0.655734 1.272736 0.125 Uiso 1 1 calc R U . . .
H19B H 0.254408 0.752672 1.216639 0.125 Uiso 1 1 calc R U . . .
C20 C 0.3577(8) 0.7683(7) 1.2768(4) 0.156(4) Uani 1 1 d . . . . .
H20A H 0.304334 0.787060 1.307576 0.235 Uiso 1 1 calc R U . . .
H20B H 0.430841 0.728669 1.301328 0.235 Uiso 1 1 calc R U . . .
H20C H 0.356941 0.825591 1.245240 0.235 Uiso 1 1 calc R U . . .
C21 C 0.5680(2) 0.9461(2) 0.72823(14) 0.0304(6) Uani 1 1 d . . . . .
C22 C 0.6169(3) 1.0077(2) 0.71180(16) 0.0373(7) Uani 1 1 d . . . . .
H22 H 0.659037 1.011546 0.745462 0.045 Uiso 1 1 calc R U . . .
C23 C 0.6060(3) 1.0647(2) 0.64664(17) 0.0444(8) Uani 1 1 d . . . . .
H23 H 0.643778 1.103755 0.637011 0.053 Uiso 1 1 calc R U . . .
C24 C 0.5418(3) 1.0651(2) 0.59652(16) 0.0430(7) Uani 1 1 d . . . . .
H24 H 0.534520 1.104742 0.552951 0.052 Uiso 1 1 calc R U . . .
C25 C 0.4873(3) 1.0066(2) 0.61023(15) 0.0367(7) Uani 1 1 d . . . . .
C26 C 0.5029(2) 0.9472(2) 0.67569(14) 0.0312(6) Uani 1 1 d . . . . .
C27 C 0.4528(2) 0.88400(19) 0.69064(14) 0.0323(6) Uani 1 1 d . . . . .
C28 C 0.3847(3) 0.8804(2) 0.64305(15) 0.0380(7) Uani 1 1 d . . . . .
C29 C 0.3672(3) 0.9439(2) 0.57756(16) 0.0432(8) Uani 1 1 d . . . . .
H29 H 0.320431 0.944085 0.544420 0.052 Uiso 1 1 calc R U . . .
C30 C 0.4157(3) 1.0032(2) 0.56218(15) 0.0428(8) Uani 1 1 d . . . . .
H30 H 0.402346 1.044031 0.518343 0.051 Uiso 1 1 calc R U . . .
C31 C 0.3399(3) 0.8148(2) 0.66173(17) 0.0449(8) Uani 1 1 d . . . . .
H31 H 0.292403 0.811277 0.630948 0.054 Uiso 1 1 calc R U . . .
C32 C 0.3658(3) 0.7555(2) 0.72536(17) 0.0454(8) Uani 1 1 d . . . . .
H32 H 0.337079 0.709787 0.738510 0.054 Uiso 1 1 calc R U . . .
C33 C 0.4340(3) 0.7619(2) 0.77078(16) 0.0389(7) Uani 1 1 d . . . . .
H33 H 0.450870 0.720207 0.814537 0.047 Uiso 1 1 calc R U . . .
C34 C 0.4289(2) 0.9550(2) 0.83623(14) 0.0334(6) Uani 1 1 d . . . . .
C35 C 0.3190(3) 0.9817(2) 0.81990(16) 0.0421(7) Uani 1 1 d . . . . .
H35 H 0.298267 0.950216 0.794336 0.051 Uiso 1 1 calc R U . . .
C36 C 0.2380(3) 1.0543(3) 0.8405(2) 0.0560(10) Uani 1 1 d . . . . .
H36 H 0.163371 1.070715 0.828771 0.067 Uiso 1 1 calc R U . . .
C37 C 0.2633(3) 1.1023(2) 0.87708(19) 0.0571(10) Uani 1 1 d . . . . .
H37 H 0.206774 1.150730 0.890881 0.069 Uiso 1 1 calc R U . . .
C38 C 0.3729(3) 1.0794(2) 0.89399(16) 0.0480(9) Uani 1 1 d . . . . .
C39 C 0.4535(3) 1.0058(2) 0.87307(14) 0.0360(7) Uani 1 1 d . . . . .
C40 C 0.5658(3) 0.9793(2) 0.88997(14) 0.0369(7) Uani 1 1 d . . . . .
C41 C 0.5993(3) 1.0280(2) 0.92426(16) 0.0483(9) Uani 1 1 d . . . . .
C42 C 0.5142(4) 1.1037(3) 0.94441(19) 0.0625(11) Uani 1 1 d . . . . .
H42 H 0.534221 1.137582 0.968161 0.075 Uiso 1 1 calc R U . . .
C43 C 0.4086(4) 1.1272(3) 0.93056(19) 0.0619(11) Uani 1 1 d . . . . .
H43 H 0.355433 1.176717 0.945199 0.074 Uiso 1 1 calc R U . . .
C44 C 0.7108(4) 0.9996(3) 0.93719(19) 0.0602(11) Uani 1 1 d . . . . .
H44 H 0.736372 1.031247 0.960081 0.072 Uiso 1 1 calc R U . . .
C45 C 0.7834(4) 0.9256(3) 0.9165(2) 0.0604(10) Uani 1 1 d . . . . .
H45 H 0.859651 0.906387 0.924539 0.072 Uiso 1 1 calc R U . . .
C46 C 0.7459(3) 0.8785(3) 0.88401(17) 0.0464(8) Uani 1 1 d . . . . .
H46 H 0.797570 0.826287 0.871145 0.056 Uiso 1 1 calc R U . . .
C47 C -0.1648(2) 0.7313(2) 0.29056(14) 0.0338(6) Uani 1 1 d . . . . .
C48 C -0.3265(3) 0.8348(2) 0.30921(17) 0.0447(8) Uani 1 1 d . . . . .
H48 H -0.403270 0.867079 0.309446 0.054 Uiso 1 1 calc R U . . .
C49 C -0.2511(3) 0.8515(2) 0.33574(16) 0.0427(7) Uani 1 1 d . . . . .
H49 H -0.263407 0.897095 0.358940 0.051 Uiso 1 1 calc R U . . .
C50 C 0.0364(2) 0.6846(2) 0.33391(13) 0.0322(6) Uani 1 1 d . . . . .
C51 C -0.0407(2) 0.7689(2) 0.34367(13) 0.0337(6) Uani 1 1 d . . . . .
C52 C -0.0139(3) 0.8281(2) 0.37185(15) 0.0403(7) Uani 1 1 d . . . . .
C53 C 0.0972(3) 0.7900(2) 0.40081(15) 0.0402(7) Uani 1 1 d . . . . .
C54 C 0.1739(3) 0.7007(2) 0.39629(16) 0.0408(7) Uani 1 1 d . . . . .
C55 C 0.1447(3) 0.6525(2) 0.36160(14) 0.0363(7) Uani 1 1 d . . . . .
H55 H 0.199638 0.595244 0.356001 0.044 Uiso 1 1 calc R U . . .
C56 C -0.0840(3) 0.9233(3) 0.3716(2) 0.0589(10) Uani 1 1 d . . . . .
H56 H -0.156365 0.953221 0.349626 0.071 Uiso 1 1 calc R U . . .
C57 C -0.0494(4) 0.9723(3) 0.4023(3) 0.0783(14) Uani 1 1 d . . . . .
H57 H -0.098326 1.035377 0.401672 0.094 Uiso 1 1 calc R U . . .
C58 C 0.0564(4) 0.9314(3) 0.4344(2) 0.0692(12) Uani 1 1 d . . . . .
H58 H 0.077864 0.965468 0.457125 0.083 Uiso 1 1 calc R U . . .
C59 C 0.1296(3) 0.8423(3) 0.43328(18) 0.0513(9) Uani 1 1 d . . . . .
C60 C 0.2426(4) 0.8006(3) 0.46597(19) 0.0576(10) Uani 1 1 d . . . . .
C61 C 0.2877(3) 0.6582(3) 0.4282(2) 0.0561(10) Uani 1 1 d . . . . .
C62 C -0.3298(3) 0.7253(3) 0.24620(18) 0.0487(8) Uani 1 1 d . . . . .
H62A H -0.408814 0.759843 0.246282 0.073 Uiso 1 1 calc R U . . .
H62B H -0.312604 0.734273 0.200621 0.073 Uiso 1 1 calc R U . . .
H62C H -0.306147 0.657020 0.268208 0.073 Uiso 1 1 calc R U . . .
C63A C 0.4323(4) 0.6694(4) 0.4934(3) 0.0818(15) Uani 0.75 1 d D . P A 1
H63A H 0.459753 0.718860 0.483038 0.098 Uiso 0.75 1 calc R U P A 1
H63B H 0.479497 0.616787 0.475891 0.098 Uiso 0.75 1 calc R U P A 1
C64A C 0.4373(5) 0.6311(4) 0.5680(3) 0.0761(18) Uani 0.75 1 d D . P A 1
H64A H 0.515146 0.596591 0.586980 0.091 Uiso 0.75 1 calc R U P A 1
H64B H 0.403084 0.686441 0.585610 0.091 Uiso 0.75 1 calc R U P A 1
C65A C 0.3830(6) 0.5648(5) 0.5929(4) 0.094(2) Uani 0.75 1 d D . P A 1
H65A H 0.303943 0.599804 0.576899 0.113 Uiso 0.75 1 calc R U P A 1
H65B H 0.414474 0.510241 0.574446 0.113 Uiso 0.75 1 calc R U P A 1
C66A C 0.3976(8) 0.5281(6) 0.6658(4) 0.105(3) Uani 0.75 1 d D . P A 1
H66A H 0.361443 0.485911 0.679407 0.158 Uiso 0.75 1 calc R U P A 1
H66B H 0.475770 0.492247 0.681830 0.158 Uiso 0.75 1 calc R U P A 1
H66C H 0.365240 0.581810 0.684283 0.158 Uiso 0.75 1 calc R U P A 1
C63B C 0.4323(4) 0.6694(4) 0.4934(3) 0.0818(15) Uani 0.25 1 d D . P A 2
H63C H 0.455337 0.602612 0.521160 0.098 Uiso 0.25 1 calc R U P A 2
H63D H 0.439495 0.707209 0.521346 0.098 Uiso 0.25 1 calc R U P A 2
C64B C 0.5024(14) 0.6732(16) 0.4350(11) 0.117(7) Uani 0.25 1 d D . P A 2
H64C H 0.480938 0.643447 0.405816 0.140 Uiso 0.25 1 calc R U P A 2
H64D H 0.474562 0.741790 0.410336 0.140 Uiso 0.25 1 calc R U P A 2
C65B C 0.6237(15) 0.634(2) 0.4387(15) 0.131(10) Uani 0.25 1 d D . P A 2
H65C H 0.657375 0.563488 0.448968 0.157 Uiso 0.25 1 calc R U P A 2
H65D H 0.645849 0.661198 0.396519 0.157 Uiso 0.25 1 calc R U P A 2
C66B C 0.656(3) 0.663(2) 0.4924(18) 0.175(16) Uani 0.25 1 d D . P A 2
H66D H 0.735896 0.639354 0.497888 0.263 Uiso 0.25 1 calc R U P A 2
H66E H 0.621532 0.732723 0.481478 0.263 Uiso 0.25 1 calc R U P A 2
H66F H 0.632984 0.635642 0.533589 0.263 Uiso 0.25 1 calc R U P A 2
C67 C -0.0920(2) 0.5639(2) 0.22560(15) 0.0339(6) Uani 1 1 d . . . . .
C69 C -0.1409(3) 0.5021(2) 0.24107(18) 0.0443(8) Uani 1 1 d . . . . .
H69 H -0.146083 0.475191 0.285967 0.053 Uiso 1 1 calc R U . . .
C70 C -0.1830(3) 0.4783(3) 0.1916(2) 0.0537(9) Uani 1 1 d . . . . .
H70 H -0.218159 0.437341 0.203925 0.064 Uiso 1 1 calc R U . . .
C71 C -0.1748(3) 0.5126(3) 0.12653(19) 0.0525(9) Uani 1 1 d . . . . .
H71 H -0.203017 0.494716 0.094247 0.063 Uiso 1 1 calc R U . . .
C72 C -0.1246(3) 0.5740(2) 0.10750(16) 0.0417(7) Uani 1 1 d . . . . .
C73 C -0.0853(2) 0.5990(2) 0.15771(15) 0.0346(6) Uani 1 1 d . . . . .
C74 C -0.0360(2) 0.6624(2) 0.14009(14) 0.0321(6) Uani 1 1 d . . . . .
C75 C -0.0219(3) 0.6999(2) 0.07399(14) 0.0392(7) Uani 1 1 d . . . . .
C76 C -0.0605(3) 0.6704(3) 0.02487(16) 0.0510(9) Uani 1 1 d . . . . .
H76 H -0.051154 0.693027 -0.019935 0.061 Uiso 1 1 calc R U . . .
C77 C -0.1092(3) 0.6117(3) 0.04082(17) 0.0521(9) Uani 1 1 d . . . . .
H77 H -0.134333 0.594621 0.006847 0.063 Uiso 1 1 calc R U . . .
C78 C 0.0267(3) 0.7626(2) 0.06126(16) 0.0459(8) Uani 1 1 d . . . . .
H78 H 0.038136 0.788343 0.017513 0.055 Uiso 1 1 calc R U . . .
C79 C 0.0577(3) 0.7868(2) 0.11228(17) 0.0459(8) Uani 1 1 d . . . . .
H79 H 0.090143 0.830044 0.104009 0.055 Uiso 1 1 calc R U . . .
C80 C 0.0415(2) 0.7478(2) 0.17635(16) 0.0382(7) Uani 1 1 d . . . . .
H80 H 0.063741 0.765064 0.211226 0.046 Uiso 1 1 calc R U . . .
C81 C 0.1284(3) 0.5053(2) 0.29240(15) 0.0386(7) Uani 1 1 d . . . . .
C82 C 0.2137(3) 0.4940(2) 0.25405(18) 0.0445(8) Uani 1 1 d . . . . .
H82 H 0.203455 0.542538 0.214077 0.053 Uiso 1 1 calc R U . . .
C83 C 0.3147(3) 0.4130(3) 0.2727(2) 0.0637(11) Uani 1 1 d . . . . .
H83 H 0.370716 0.407494 0.244813 0.076 Uiso 1 1 calc R U . . .
C84 C 0.3340(4) 0.3425(3) 0.3296(3) 0.0877(17) Uani 1 1 d . . . . .
H84 H 0.403140 0.288419 0.341638 0.105 Uiso 1 1 calc R U . . .
C85 C 0.2514(5) 0.3498(3) 0.3707(2) 0.0890(18) Uani 1 1 d . . . . .
C86 C 0.1500(4) 0.4315(3) 0.35100(18) 0.0590(11) Uani 1 1 d . . . . .
C87 C 0.0646(4) 0.4424(3) 0.39186(17) 0.0651(12) Uani 1 1 d . . . . .
C88 C 0.0756(6) 0.3732(3) 0.4504(2) 0.102(2) Uani 1 1 d . . . . .
C89 C 0.1788(8) 0.2907(4) 0.4699(3) 0.161(4) Uani 1 1 d . . . . .
H89 H 0.189688 0.242989 0.510397 0.193 Uiso 1 1 calc R U . . .
C90 C 0.2614(7) 0.2792(4) 0.4318(3) 0.145(4) Uani 1 1 d . . . . .
H90 H 0.327950 0.222631 0.445829 0.174 Uiso 1 1 calc R U . . .
C91 C -0.0142(7) 0.3901(4) 0.4872(2) 0.118(3) Uani 1 1 d . . . . .
H91 H -0.009790 0.343863 0.527317 0.142 Uiso 1 1 calc R U . . .
C92 C -0.1079(6) 0.4737(4) 0.4647(2) 0.095(2) Uani 1 1 d . . . . .
H92 H -0.168722 0.485504 0.489212 0.114 Uiso 1 1 calc R U . . .
C93 C -0.1137(4) 0.5405(3) 0.40649(18) 0.0622(11) Uani 1 1 d . . . . .
H93 H -0.178778 0.598334 0.391731 0.075 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N5 2.057(2) . ?
Ir1 N4 2.060(2) . ?
Ir1 C34 2.067(3) . ?
Ir1 C1 2.069(3) . ?
Ir1 C21 2.079(3) . ?
Ir1 C4 2.100(3) . ?
Ir2 N10 2.056(3) . ?
Ir2 N9 2.057(2) . ?
Ir2 C81 2.064(3) . ?
Ir2 C47 2.066(3) . ?
Ir2 C67 2.077(3) . ?
Ir2 C50 2.105(3) . ?
O1 C15 1.225(4) . ?
O2 C14 1.214(4) . ?
O3 C61 1.208(5) . ?
O4 C60 1.223(4) . ?
N1 C1 1.373(4) . ?
N1 C3 1.394(4) . ?
N1 C5 1.419(4) . ?
N2 C1 1.337(4) . ?
N2 C2 1.387(4) . ?
N2 C16 1.455(5) . ?
N3 C14 1.392(4) . ?
N3 C15 1.398(4) . ?
N3 C17 1.468(4) . ?
N4 C33 1.329(4) . ?
N4 C27 1.377(4) . ?
N5 C46 1.341(4) . ?
N5 C40 1.371(4) . ?
N6 C47 1.376(4) . ?
N6 C49 1.391(4) . ?
N6 C51 1.429(4) . ?
N7 C47 1.338(4) . ?
N7 C48 1.388(4) . ?
N7 C62 1.453(4) . ?
N8 C60 1.386(5) . ?
N8 C61 1.409(5) . ?
N8 C63B 1.521(5) . ?
N8 C63A 1.521(5) . ?
N9 C80 1.331(4) . ?
N9 C74 1.371(4) . ?
N10 C93 1.343(5) . ?
N10 C87 1.381(5) . ?
C2 C3 1.328(5) . ?
C4 C5 1.404(4) . ?
C4 C9 1.410(4) . ?
C5 C6 1.421(4) . ?
C6 C10 1.422(4) . ?
C6 C7 1.429(4) . ?
C7 C13 1.413(4) . ?
C7 C8 1.417(4) . ?
C8 C9 1.374(4) . ?
C8 C15 1.462(4) . ?
C10 C11 1.368(5) . ?
C11 C12 1.394(5) . ?
C12 C13 1.376(4) . ?
C13 C14 1.478(5) . ?
C17 C18 1.565(6) . ?
C18 C19 1.482(7) . ?
C19 C20 1.487(8) . ?
C21 C22 1.382(4) . ?
C21 C26 1.420(4) . ?
C22 C23 1.408(5) . ?
C23 C24 1.378(5) . ?
C24 C25 1.399(5) . ?
C25 C26 1.416(4) . ?
C25 C30 1.441(4) . ?
C26 C27 1.417(4) . ?
C27 C28 1.404(4) . ?
C28 C31 1.399(5) . ?
C28 C29 1.438(5) . ?
C29 C30 1.346(5) . ?
C31 C32 1.374(5) . ?
C32 C33 1.394(5) . ?
C34 C35 1.386(4) . ?
C34 C39 1.406(4) . ?
C35 C36 1.401(5) . ?
C36 C37 1.367(6) . ?
C37 C38 1.398(6) . ?
C38 C39 1.411(4) . ?
C38 C43 1.440(6) . ?
C39 C40 1.420(5) . ?
C40 C41 1.403(4) . ?
C41 C44 1.391(6) . ?
C41 C42 1.449(6) . ?
C42 C43 1.333(7) . ?
C44 C45 1.370(6) . ?
C45 C46 1.388(5) . ?
C48 C49 1.327(5) . ?
C50 C51 1.393(4) . ?
C50 C55 1.409(4) . ?
C51 C52 1.418(4) . ?
C52 C56 1.425(5) . ?
C52 C53 1.436(5) . ?
C53 C54 1.407(5) . ?
C53 C59 1.418(4) . ?
C54 C55 1.370(4) . ?
C54 C61 1.480(5) . ?
C56 C57 1.366(6) . ?
C57 C58 1.392(6) . ?
C58 C59 1.368(6) . ?
C59 C60 1.478(6) . ?
C63A C64A 1.526(8) . ?
C64A C65A 1.522(9) . ?
C65A C66A 1.480(9) . ?
C63B C64B 1.562(16) . ?
C64B C65B 1.489(17) . ?
C65B C66B 1.477(18) . ?
C67 C69 1.385(5) . ?
C67 C73 1.416(4) . ?
C69 C70 1.411(5) . ?
C70 C71 1.364(6) . ?
C71 C72 1.399(5) . ?
C72 C73 1.416(4) . ?
C72 C77 1.433(5) . ?
C73 C74 1.413(4) . ?
C74 C75 1.416(4) . ?
C75 C78 1.393(5) . ?
C75 C76 1.440(5) . ?
C76 C77 1.341(6) . ?
C78 C79 1.370(5) . ?
C79 C80 1.394(5) . ?
C81 C82 1.389(5) . ?
C81 C86 1.400(5) . ?
C82 C83 1.403(5) . ?
C83 C84 1.353(7) . ?
C84 C85 1.401(8) . ?
C85 C86 1.412(6) . ?
C85 C90 1.439(8) . ?
C86 C87 1.423(6) . ?
C87 C88 1.387(6) . ?
C88 C91 1.413(9) . ?
C88 C89 1.432(9) . ?
C89 C90 1.356(12) . ?
C91 C92 1.373(9) . ?
C92 C93 1.381(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
N5 Ir1 N4 168.62(9) . . ?
N5 Ir1 C34 80.35(11) . . ?
N4 Ir1 C34 91.04(11) . . ?
N5 Ir1 C1 94.26(11) . . ?
N4 Ir1 C1 95.47(10) . . ?
C34 Ir1 C1 168.83(11) . . ?
N5 Ir1 C21 92.02(11) . . ?
N4 Ir1 C21 80.61(11) . . ?
C34 Ir1 C21 90.87(11) . . ?
C1 Ir1 C21 99.13(11) . . ?
N5 Ir1 C4 93.44(10) . . ?
N4 Ir1 C4 94.45(10) . . ?
C34 Ir1 C4 93.11(11) . . ?
C1 Ir1 C4 77.37(11) . . ?
C21 Ir1 C4 173.72(10) . . ?
N10 Ir2 N9 169.94(10) . . ?
N10 Ir2 C81 80.60(13) . . ?
N9 Ir2 C81 91.44(11) . . ?
N10 Ir2 C47 93.94(12) . . ?
N9 Ir2 C47 94.96(10) . . ?
C81 Ir2 C47 168.38(11) . . ?
N10 Ir2 C67 93.59(12) . . ?
N9 Ir2 C67 80.40(11) . . ?
C81 Ir2 C67 91.61(11) . . ?
C47 Ir2 C67 99.00(12) . . ?
N10 Ir2 C50 90.94(11) . . ?
N9 Ir2 C50 95.55(10) . . ?
C81 Ir2 C50 92.28(11) . . ?
C47 Ir2 C50 77.48(12) . . ?
C67 Ir2 C50 174.46(11) . . ?
C1 N1 C3 109.9(3) . . ?
C1 N1 C5 117.3(2) . . ?
C3 N1 C5 132.3(3) . . ?
C1 N2 C2 110.8(3) . . ?
C1 N2 C16 125.5(3) . . ?
C2 N2 C16 123.7(3) . . ?
C14 N3 C15 124.5(3) . . ?
C14 N3 C17 119.0(3) . . ?
C15 N3 C17 116.5(3) . . ?
C33 N4 C27 119.1(3) . . ?
C33 N4 Ir1 126.7(2) . . ?
C27 N4 Ir1 114.08(19) . . ?
C46 N5 C40 118.0(3) . . ?
C46 N5 Ir1 127.6(2) . . ?
C40 N5 Ir1 114.3(2) . . ?
C47 N6 C49 109.9(3) . . ?
C47 N6 C51 117.2(2) . . ?
C49 N6 C51 132.3(3) . . ?
C47 N7 C48 110.7(3) . . ?
C47 N7 C62 125.9(3) . . ?
C48 N7 C62 123.4(3) . . ?
C60 N8 C61 124.2(3) . . ?
C60 N8 C63B 118.3(3) . . ?
C61 N8 C63B 117.5(3) . . ?
C60 N8 C63A 118.3(3) . . ?
C61 N8 C63A 117.5(3) . . ?
C80 N9 C74 118.6(3) . . ?
C80 N9 Ir2 126.9(2) . . ?
C74 N9 Ir2 114.34(19) . . ?
C93 N10 C87 118.9(3) . . ?
C93 N10 Ir2 127.3(3) . . ?
C87 N10 Ir2 113.8(3) . . ?
N2 C1 N1 104.9(2) . . ?
N2 C1 Ir1 138.4(2) . . ?
N1 C1 Ir1 115.8(2) . . ?
C3 C2 N2 107.7(3) . . ?
C2 C3 N1 106.6(3) . . ?
C5 C4 C9 115.7(3) . . ?
C5 C4 Ir1 115.9(2) . . ?
C9 C4 Ir1 128.4(2) . . ?
C4 C5 N1 113.0(3) . . ?
C4 C5 C6 124.1(3) . . ?
N1 C5 C6 122.9(2) . . ?
C5 C6 C10 126.6(3) . . ?
C5 C6 C7 116.4(3) . . ?
C10 C6 C7 117.0(3) . . ?
C13 C7 C8 120.5(3) . . ?
C13 C7 C6 119.8(3) . . ?
C8 C7 C6 119.7(3) . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 C15 120.1(3) . . ?
C7 C8 C15 119.7(3) . . ?
C8 C9 C4 122.9(3) . . ?
C11 C10 C6 121.4(3) . . ?
C10 C11 C12 120.9(3) . . ?
C13 C12 C11 119.8(3) . . ?
C12 C13 C7 120.6(3) . . ?
C12 C13 C14 119.5(3) . . ?
C7 C13 C14 119.9(3) . . ?
O2 C14 N3 120.9(3) . . ?
O2 C14 C13 122.3(3) . . ?
N3 C14 C13 116.9(3) . . ?
O1 C15 N3 119.2(3) . . ?
O1 C15 C8 123.2(3) . . ?
N3 C15 C8 117.6(3) . . ?
N3 C17 C18 110.1(3) . . ?
C19 C18 C17 111.4(4) . . ?
C18 C19 C20 112.2(5) . . ?
C22 C21 C26 115.6(3) . . ?
C22 C21 Ir1 132.8(2) . . ?
C26 C21 Ir1 111.5(2) . . ?
C21 C22 C23 121.9(3) . . ?
C24 C23 C22 121.4(3) . . ?
C23 C24 C25 119.5(3) . . ?
C24 C25 C26 117.9(3) . . ?
C24 C25 C30 124.3(3) . . ?
C26 C25 C30 117.8(3) . . ?
C25 C26 C27 119.4(3) . . ?
C25 C26 C21 123.5(3) . . ?
C27 C26 C21 117.1(3) . . ?
N4 C27 C28 121.4(3) . . ?
N4 C27 C26 116.4(3) . . ?
C28 C27 C26 122.1(3) . . ?
C31 C28 C27 118.4(3) . . ?
C31 C28 C29 124.3(3) . . ?
C27 C28 C29 117.2(3) . . ?
C30 C29 C28 121.5(3) . . ?
C29 C30 C25 122.0(3) . . ?
C32 C31 C28 118.8(3) . . ?
C31 C32 C33 120.5(3) . . ?
N4 C33 C32 121.6(3) . . ?
C35 C34 C39 116.3(3) . . ?
C35 C34 Ir1 131.4(2) . . ?
C39 C34 Ir1 112.3(2) . . ?
C34 C35 C36 121.0(3) . . ?
C37 C36 C35 121.9(4) . . ?
C36 C37 C38 119.5(3) . . ?
C37 C38 C39 117.9(3) . . ?
C37 C38 C43 124.1(3) . . ?
C39 C38 C43 118.0(4) . . ?
C34 C39 C38 123.3(3) . . ?
C34 C39 C40 116.8(3) . . ?
C38 C39 C40 119.8(3) . . ?
N5 C40 C41 122.3(3) . . ?
N5 C40 C39 116.2(3) . . ?
C41 C40 C39 121.5(3) . . ?
C44 C41 C40 118.1(3) . . ?
C44 C41 C42 124.9(3) . . ?
C40 C41 C42 117.1(4) . . ?
C43 C42 C41 121.8(4) . . ?
C42 C43 C38 121.8(3) . . ?
C45 C44 C41 119.3(3) . . ?
C44 C45 C46 120.3(4) . . ?
N5 C46 C45 122.1(4) . . ?
N7 C47 N6 104.8(3) . . ?
N7 C47 Ir2 138.6(2) . . ?
N6 C47 Ir2 115.8(2) . . ?
C49 C48 N7 107.7(3) . . ?
C48 C49 N6 106.7(3) . . ?
C51 C50 C55 116.3(3) . . ?
C51 C50 Ir2 116.0(2) . . ?
C55 C50 Ir2 127.7(2) . . ?
C50 C51 C52 123.8(3) . . ?
C50 C51 N6 113.1(3) . . ?
C52 C51 N6 123.1(3) . . ?
C51 C52 C56 126.9(3) . . ?
C51 C52 C53 116.5(3) . . ?
C56 C52 C53 116.5(3) . . ?
C54 C53 C59 120.3(3) . . ?
C54 C53 C52 119.5(3) . . ?
C59 C53 C52 120.2(3) . . ?
C55 C54 C53 120.5(3) . . ?
C55 C54 C61 119.0(3) . . ?
C53 C54 C61 120.4(3) . . ?
C54 C55 C50 122.5(3) . . ?
C57 C56 C52 121.4(4) . . ?
C56 C57 C58 121.1(4) . . ?
C59 C58 C57 120.4(4) . . ?
C58 C59 C53 120.1(4) . . ?
C58 C59 C60 119.9(3) . . ?
C53 C59 C60 120.0(3) . . ?
O4 C60 N8 120.6(4) . . ?
O4 C60 C59 121.5(4) . . ?
N8 C60 C59 117.9(3) . . ?
O3 C61 N8 119.9(3) . . ?
O3 C61 C54 123.0(3) . . ?
N8 C61 C54 117.1(3) . . ?
N8 C63A C64A 110.2(5) . . ?
C65A C64A C63A 116.9(5) . . ?
C66A C65A C64A 112.4(7) . . ?
N8 C63B C64B 105.0(8) . . ?
C65B C64B C63B 127.7(18) . . ?
C66B C65B C64B 104.7(19) . . ?
C69 C67 C73 115.6(3) . . ?
C69 C67 Ir2 132.8(2) . . ?
C73 C67 Ir2 111.6(2) . . ?
C67 C69 C70 121.4(3) . . ?
C71 C70 C69 121.8(3) . . ?
C70 C71 C72 119.8(3) . . ?
C71 C72 C73 117.6(3) . . ?
C71 C72 C77 124.1(3) . . ?
C73 C72 C77 118.3(3) . . ?
C74 C73 C67 117.1(3) . . ?
C74 C73 C72 119.0(3) . . ?
C67 C73 C72 123.8(3) . . ?
N9 C74 C73 116.3(3) . . ?
N9 C74 C75 121.4(3) . . ?
C73 C74 C75 122.2(3) . . ?
C78 C75 C74 118.2(3) . . ?
C78 C75 C76 125.1(3) . . ?
C74 C75 C76 116.7(3) . . ?
C77 C76 C75 121.6(3) . . ?
C76 C77 C72 122.1(3) . . ?
C79 C78 C75 119.5(3) . . ?
C78 C79 C80 119.7(3) . . ?
N9 C80 C79 122.5(3) . . ?
C82 C81 C86 115.8(3) . . ?
C82 C81 Ir2 131.5(3) . . ?
C86 C81 Ir2 112.4(3) . . ?
C81 C82 C83 121.8(4) . . ?
C84 C83 C82 121.4(4) . . ?
C83 C84 C85 119.5(4) . . ?
C84 C85 C86 118.3(4) . . ?
C84 C85 C90 124.8(5) . . ?
C86 C85 C90 116.9(6) . . ?
C81 C86 C85 123.1(4) . . ?
C81 C86 C87 116.9(3) . . ?
C85 C86 C87 120.1(4) . . ?
N10 C87 C88 121.7(4) . . ?
N10 C87 C86 116.2(3) . . ?
C88 C87 C86 122.2(4) . . ?
C87 C88 C91 118.0(5) . . ?
C87 C88 C89 117.2(6) . . ?
C91 C88 C89 124.7(5) . . ?
C90 C89 C88 121.5(5) . . ?
C89 C90 C85 122.1(6) . . ?
C92 C91 C88 119.5(4) . . ?
C91 C92 C93 119.9(5) . . ?
N10 C93 C92 122.0(5) . . ?


####################################################################### 
# 
# 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_Compound_5b
_database_code_depnum_ccdc_archive 'CCDC 1477778'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C50 H36 Ir N5 O2'
_chemical_formula_sum            'C50 H36 Ir N5 O2'
_chemical_formula_weight         931.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 '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                   9.3652(4)
_cell_length_b                   12.4098(5)
_cell_length_c                   16.8233(7)
_cell_angle_alpha                99.293(2)
_cell_angle_beta                 98.218(2)
_cell_angle_gamma                90.072(2)
_cell_volume                     1909.14(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9357
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      66.61

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    7.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            26772
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.610
_diffrn_reflns_theta_max         66.607
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6729
_reflns_number_gt                6496
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+2.3641P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6729
_refine_ls_number_parameters     524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0644
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.850
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.084

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.62355(2) 0.26028(2) 0.27106(2) 0.02410(6) Uani 1 1 d . . . . .
O1 O 0.1130(3) 0.7946(2) 0.1828(2) 0.0527(7) Uani 1 1 d . . . . .
O2 O 0.0651(3) 0.4369(2) 0.19878(17) 0.0424(6) Uani 1 1 d . . . . .
N1 N 0.7422(3) 0.4852(2) 0.32288(16) 0.0266(5) Uani 1 1 d . . . . .
N2 N 0.9258(3) 0.3790(2) 0.34200(16) 0.0288(6) Uani 1 1 d . . . . .
N3 N 0.0874(3) 0.6176(2) 0.19741(17) 0.0320(6) Uani 1 1 d . . . . .
N4 N 0.6469(3) 0.2465(2) 0.15046(16) 0.0323(6) Uani 1 1 d . . . . .
N5 N 0.5868(3) 0.2487(2) 0.38725(15) 0.0281(6) Uani 1 1 d . . . . .
C1 C 0.7841(3) 0.3771(3) 0.31176(19) 0.0271(6) Uani 1 1 d . . . . .
C2 C 0.9737(4) 0.4836(3) 0.3774(2) 0.0312(7) Uani 1 1 d . . . . .
C3 C 0.8562(3) 0.5520(3) 0.36880(18) 0.0280(6) Uani 1 1 d . . . . .
C4 C 0.8708(4) 0.6601(3) 0.4087(2) 0.0327(7) Uani 1 1 d . . . . .
H4 H 0.791371 0.707669 0.407052 0.039 Uiso 1 1 calc R U . . .
C5 C 1.0047(4) 0.6956(3) 0.4506(2) 0.0409(8) Uani 1 1 d . . . . .
H5 H 1.016956 0.769151 0.477361 0.049 Uiso 1 1 calc R U . . .
C6 C 1.1222(4) 0.6272(3) 0.4548(2) 0.0454(9) Uani 1 1 d . . . . .
H6 H 1.213267 0.655131 0.482934 0.054 Uiso 1 1 calc R U . . .
C7 C 1.1075(4) 0.5201(3) 0.4189(2) 0.0401(8) Uani 1 1 d . . . . .
H7 H 1.186633 0.472447 0.422250 0.048 Uiso 1 1 calc R U . . .
C8 C 0.5125(4) 0.4061(3) 0.26724(19) 0.0274(6) Uani 1 1 d . . . . .
C9 C 0.5948(3) 0.5027(3) 0.28947(18) 0.0264(6) Uani 1 1 d . . . . .
C10 C 0.5408(3) 0.6056(3) 0.27304(18) 0.0271(6) Uani 1 1 d . . . . .
C11 C 0.3883(3) 0.6103(3) 0.24813(18) 0.0271(6) Uani 1 1 d . . . . .
C12 C 0.3011(3) 0.5141(3) 0.23590(19) 0.0286(7) Uani 1 1 d . . . . .
C13 C 0.3646(3) 0.4155(3) 0.2422(2) 0.0300(7) Uani 1 1 d . . . . .
H13 H 0.305665 0.350925 0.228878 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6227(4) 0.7016(3) 0.27195(19) 0.0295(7) Uani 1 1 d . . . . .
H14 H 0.724865 0.700161 0.283845 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5602(4) 0.7954(3) 0.2545(2) 0.0326(7) Uani 1 1 d . . . . .
H15 H 0.619259 0.858000 0.255360 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4104(4) 0.8014(3) 0.2353(2) 0.0328(7) Uani 1 1 d . . . . .
H16 H 0.367462 0.868314 0.225661 0.039 Uiso 1 1 calc R U . . .
C17 C 0.3260(4) 0.7091(3) 0.23053(19) 0.0293(7) Uani 1 1 d . . . . .
C18 C 0.1697(4) 0.7129(3) 0.2023(2) 0.0348(7) Uani 1 1 d . . . . .
C19 C 0.1443(4) 0.5171(3) 0.2097(2) 0.0324(7) Uani 1 1 d . . . . .
C20 C 1.0196(4) 0.2848(3) 0.3354(2) 0.0375(8) Uani 1 1 d . . . . .
H20A H 0.961891 0.218845 0.310744 0.056 Uiso 1 1 calc R U . . .
H20B H 1.067006 0.276165 0.389765 0.056 Uiso 1 1 calc R U . . .
H20C H 1.092972 0.296418 0.301306 0.056 Uiso 1 1 calc R U . . .
C21 C -0.0695(3) 0.6226(3) 0.1725(2) 0.0355(7) Uani 1 1 d . . . . .
H21A H -0.101194 0.697244 0.191510 0.043 Uiso 1 1 calc R U . . .
H21B H -0.119122 0.571497 0.199592 0.043 Uiso 1 1 calc R U . . .
C22 C -0.1149(4) 0.5946(4) 0.0818(2) 0.0452(9) Uani 1 1 d . . . . .
H22A H -0.078474 0.521878 0.061837 0.054 Uiso 1 1 calc R U . . .
H22B H -0.071289 0.648780 0.054574 0.054 Uiso 1 1 calc R U . . .
C23 C -0.2776(4) 0.5937(4) 0.0594(3) 0.0569(11) Uani 1 1 d . . . . .
H23A H -0.320761 0.538727 0.086081 0.068 Uiso 1 1 calc R U . . .
H23B H -0.313864 0.666041 0.080417 0.068 Uiso 1 1 calc R U . . .
C24 C -0.3255(6) 0.5678(6) -0.0309(3) 0.0780(16) Uani 1 1 d . . . . .
H24A H -0.431091 0.568211 -0.041984 0.117 Uiso 1 1 calc R U . . .
H24B H -0.284880 0.622840 -0.057572 0.117 Uiso 1 1 calc R U . . .
H24C H -0.291780 0.495489 -0.051907 0.117 Uiso 1 1 calc R U . . .
C25 C 0.4417(3) 0.1652(3) 0.2207(2) 0.0302(7) Uani 1 1 d . . . . .
C26 C 0.3332(4) 0.1220(3) 0.2551(2) 0.0391(8) Uani 1 1 d . . . . .
H26 H 0.339251 0.131017 0.312669 0.047 Uiso 1 1 calc R U . . .
C27 C 0.2147(4) 0.0653(3) 0.2058(3) 0.0531(11) Uani 1 1 d . . . . .
H27 H 0.141697 0.036680 0.230945 0.064 Uiso 1 1 calc R U . . .
C28 C 0.2008(5) 0.0497(4) 0.1230(3) 0.0635(13) Uani 1 1 d . . . . .
H28 H 0.118674 0.011212 0.091356 0.076 Uiso 1 1 calc R U . . .
C29 C 0.3072(5) 0.0904(4) 0.0844(3) 0.0560(11) Uani 1 1 d . . . . .
C30 C 0.4259(4) 0.1475(3) 0.1350(2) 0.0381(8) Uani 1 1 d . . . . .
C31 C 0.3048(7) 0.0769(5) -0.0024(3) 0.0770(16) Uani 1 1 d . . . . .
H31 H 0.224678 0.039826 -0.037128 0.092 Uiso 1 1 calc R U . . .
C32 C 0.4124(7) 0.1152(5) -0.0359(3) 0.0776(16) Uani 1 1 d . . . . .
H32 H 0.406631 0.103914 -0.093515 0.093 Uiso 1 1 calc R U . . .
C33 C 0.5368(4) 0.1898(3) 0.0981(2) 0.0399(8) Uani 1 1 d . . . . .
C34 C 0.5364(6) 0.1729(4) 0.0132(2) 0.0585(12) Uani 1 1 d . . . . .
C35 C 0.6539(7) 0.2124(5) -0.0165(3) 0.0757(16) Uani 1 1 d . . . . .
H35 H 0.657291 0.201519 -0.073355 0.091 Uiso 1 1 calc R U . . .
C36 C 0.7644(6) 0.2668(4) 0.0367(3) 0.0671(14) Uani 1 1 d . . . . .
H36 H 0.845436 0.293246 0.016899 0.080 Uiso 1 1 calc R U . . .
C37 C 0.7580(4) 0.2835(3) 0.1203(2) 0.0444(9) Uani 1 1 d . . . . .
H37 H 0.834987 0.322289 0.156611 0.053 Uiso 1 1 calc R U . . .
C38 C 0.7350(3) 0.1194(3) 0.2875(2) 0.0287(7) Uani 1 1 d . . . . .
C39 C 0.8115(4) 0.0482(3) 0.2371(2) 0.0362(8) Uani 1 1 d . . . . .
H39 H 0.813919 0.059856 0.182881 0.043 Uiso 1 1 calc R U . . .
C40 C 0.8848(4) -0.0399(3) 0.2647(3) 0.0461(10) Uani 1 1 d . . . . .
H40 H 0.936442 -0.086297 0.228805 0.055 Uiso 1 1 calc R U . . .
C41 C 0.8841(4) -0.0614(3) 0.3425(3) 0.0477(10) Uani 1 1 d . . . . .
H41 H 0.937943 -0.120096 0.360320 0.057 Uiso 1 1 calc R U . . .
C42 C 0.8039(4) 0.0036(3) 0.3951(3) 0.0427(9) Uani 1 1 d . . . . .
C43 C 0.7316(4) 0.0928(3) 0.3655(2) 0.0316(7) Uani 1 1 d . . . . .
C44 C 0.7874(5) -0.0141(4) 0.4761(3) 0.0562(11) Uani 1 1 d . . . . .
H44 H 0.835707 -0.073224 0.496797 0.067 Uiso 1 1 calc R U . . .
C45 C 0.7061(5) 0.0503(4) 0.5239(3) 0.0578(12) Uani 1 1 d . . . . .
H45 H 0.698029 0.035027 0.576599 0.069 Uiso 1 1 calc R U . . .
C46 C 0.6487(4) 0.1615(3) 0.4176(2) 0.0315(7) Uani 1 1 d . . . . .
C47 C 0.6321(4) 0.1408(3) 0.4961(2) 0.0427(9) Uani 1 1 d . . . . .
C48 C 0.5476(5) 0.2122(4) 0.5415(2) 0.0520(10) Uani 1 1 d . . . . .
H48 H 0.533300 0.200763 0.594341 0.062 Uiso 1 1 calc R U . . .
C49 C 0.4856(4) 0.2987(4) 0.5098(2) 0.0494(10) Uani 1 1 d . . . . .
H49 H 0.427687 0.347169 0.540433 0.059 Uiso 1 1 calc R U . . .
C50 C 0.5074(4) 0.3155(3) 0.4324(2) 0.0379(8) Uani 1 1 d . . . . .
H50 H 0.464485 0.376195 0.411270 0.045 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N4 2.052(3) . ?
Ir1 C1 2.052(3) . ?
Ir1 N5 2.060(3) . ?
Ir1 C25 2.066(3) . ?
Ir1 C38 2.074(3) . ?
Ir1 C8 2.093(3) . ?
O1 C18 1.216(4) . ?
O2 C19 1.214(4) . ?
N1 C1 1.388(4) . ?
N1 C3 1.407(4) . ?
N1 C9 1.445(4) . ?
N2 C1 1.350(4) . ?
N2 C2 1.384(4) . ?
N2 C20 1.462(4) . ?
N3 C19 1.391(4) . ?
N3 C18 1.396(5) . ?
N3 C21 1.474(4) . ?
N4 C37 1.332(5) . ?
N4 C33 1.369(5) . ?
N5 C50 1.333(4) . ?
N5 C46 1.365(4) . ?
C2 C7 1.381(5) . ?
C2 C3 1.396(5) . ?
C3 C4 1.398(5) . ?
C4 C5 1.381(5) . ?
C5 C6 1.391(6) . ?
C6 C7 1.366(5) . ?
C8 C9 1.394(4) . ?
C8 C13 1.399(5) . ?
C9 C10 1.427(4) . ?
C10 C14 1.420(5) . ?
C10 C11 1.434(4) . ?
C11 C17 1.415(5) . ?
C11 C12 1.415(5) . ?
C12 C13 1.374(5) . ?
C12 C19 1.474(5) . ?
C14 C15 1.359(5) . ?
C15 C16 1.399(5) . ?
C16 C17 1.376(5) . ?
C17 C18 1.477(5) . ?
C21 C22 1.508(5) . ?
C22 C23 1.515(5) . ?
C23 C24 1.502(6) . ?
C25 C26 1.387(5) . ?
C25 C30 1.409(5) . ?
C26 C27 1.400(6) . ?
C27 C28 1.363(7) . ?
C28 C29 1.399(7) . ?
C29 C30 1.413(5) . ?
C29 C31 1.440(7) . ?
C30 C33 1.424(5) . ?
C31 C32 1.344(8) . ?
C32 C34 1.441(7) . ?
C33 C34 1.408(5) . ?
C34 C35 1.391(7) . ?
C35 C36 1.366(8) . ?
C36 C37 1.398(6) . ?
C38 C39 1.395(5) . ?
C38 C43 1.409(5) . ?
C39 C40 1.399(5) . ?
C40 C41 1.377(6) . ?
C41 C42 1.400(6) . ?
C42 C43 1.419(5) . ?
C42 C44 1.445(6) . ?
C43 C46 1.433(5) . ?
C44 C45 1.354(7) . ?
C45 C47 1.427(6) . ?
C46 C47 1.415(5) . ?
C47 C48 1.397(6) . ?
C48 C49 1.368(6) . ?
C49 C50 1.394(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
N4 Ir1 C1 95.44(12) . . ?
N4 Ir1 N5 170.78(10) . . ?
C1 Ir1 N5 92.89(11) . . ?
N4 Ir1 C25 80.90(12) . . ?
C1 Ir1 C25 169.42(12) . . ?
N5 Ir1 C25 91.56(12) . . ?
N4 Ir1 C38 94.12(12) . . ?
C1 Ir1 C38 100.96(12) . . ?
N5 Ir1 C38 80.40(12) . . ?
C25 Ir1 C38 89.24(12) . . ?
N4 Ir1 C8 91.53(12) . . ?
C1 Ir1 C8 77.29(12) . . ?
N5 Ir1 C8 94.14(11) . . ?
C25 Ir1 C8 92.83(12) . . ?
C38 Ir1 C8 174.22(12) . . ?
C1 N1 C3 109.7(3) . . ?
C1 N1 C9 115.1(2) . . ?
C3 N1 C9 135.1(3) . . ?
C1 N2 C2 111.1(3) . . ?
C1 N2 C20 125.2(3) . . ?
C2 N2 C20 123.6(3) . . ?
C19 N3 C18 124.5(3) . . ?
C19 N3 C21 118.0(3) . . ?
C18 N3 C21 117.4(3) . . ?
C37 N4 C33 119.0(3) . . ?
C37 N4 Ir1 126.7(2) . . ?
C33 N4 Ir1 114.3(2) . . ?
C50 N5 C46 119.1(3) . . ?
C50 N5 Ir1 126.3(2) . . ?
C46 N5 Ir1 114.6(2) . . ?
N2 C1 N1 106.0(3) . . ?
N2 C1 Ir1 136.6(2) . . ?
N1 C1 Ir1 116.8(2) . . ?
C7 C2 N2 129.8(3) . . ?
C7 C2 C3 122.8(3) . . ?
N2 C2 C3 107.3(3) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 N1 105.6(3) . . ?
C4 C3 N1 135.4(3) . . ?
C5 C4 C3 117.7(3) . . ?
C4 C5 C6 122.3(3) . . ?
C7 C6 C5 120.5(3) . . ?
C6 C7 C2 117.7(3) . . ?
C9 C8 C13 117.1(3) . . ?
C9 C8 Ir1 116.7(2) . . ?
C13 C8 Ir1 126.2(2) . . ?
C8 C9 C10 122.6(3) . . ?
C8 C9 N1 112.7(3) . . ?
C10 C9 N1 124.4(3) . . ?
C14 C10 C9 127.1(3) . . ?
C14 C10 C11 116.1(3) . . ?
C9 C10 C11 116.6(3) . . ?
C17 C11 C12 119.8(3) . . ?
C17 C11 C10 120.2(3) . . ?
C12 C11 C10 119.9(3) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 C19 119.4(3) . . ?
C11 C12 C19 120.7(3) . . ?
C12 C13 C8 122.8(3) . . ?
C15 C14 C10 122.4(3) . . ?
C14 C15 C16 121.1(3) . . ?
C17 C16 C15 119.1(3) . . ?
C16 C17 C11 120.9(3) . . ?
C16 C17 C18 118.9(3) . . ?
C11 C17 C18 120.2(3) . . ?
O1 C18 N3 120.3(3) . . ?
O1 C18 C17 122.3(3) . . ?
N3 C18 C17 117.4(3) . . ?
O2 C19 N3 119.8(3) . . ?
O2 C19 C12 123.1(3) . . ?
N3 C19 C12 117.1(3) . . ?
N3 C21 C22 113.6(3) . . ?
C21 C22 C23 111.8(3) . . ?
C24 C23 C22 112.8(4) . . ?
C26 C25 C30 116.4(3) . . ?
C26 C25 Ir1 132.2(3) . . ?
C30 C25 Ir1 111.3(2) . . ?
C25 C26 C27 120.6(4) . . ?
C28 C27 C26 122.1(4) . . ?
C27 C28 C29 120.1(4) . . ?
C28 C29 C30 117.0(4) . . ?
C28 C29 C31 124.8(4) . . ?
C30 C29 C31 118.2(4) . . ?
C25 C30 C29 123.7(4) . . ?
C25 C30 C33 117.5(3) . . ?
C29 C30 C33 118.7(4) . . ?
C32 C31 C29 122.0(4) . . ?
C31 C32 C34 121.7(4) . . ?
N4 C33 C34 121.5(4) . . ?
N4 C33 C30 115.8(3) . . ?
C34 C33 C30 122.7(4) . . ?
C35 C34 C33 118.2(4) . . ?
C35 C34 C32 125.3(4) . . ?
C33 C34 C32 116.5(4) . . ?
C36 C35 C34 119.6(4) . . ?
C35 C36 C37 119.9(4) . . ?
N4 C37 C36 121.8(4) . . ?
C39 C38 C43 115.3(3) . . ?
C39 C38 Ir1 132.6(3) . . ?
C43 C38 Ir1 112.1(2) . . ?
C38 C39 C40 121.4(4) . . ?
C41 C40 C39 121.9(4) . . ?
C40 C41 C42 119.7(3) . . ?
C41 C42 C43 117.0(4) . . ?
C41 C42 C44 125.2(4) . . ?
C43 C42 C44 117.8(4) . . ?
C38 C43 C42 124.5(3) . . ?
C38 C43 C46 116.7(3) . . ?
C42 C43 C46 118.7(3) . . ?
C45 C44 C42 122.7(4) . . ?
C44 C45 C47 121.0(4) . . ?
N5 C46 C47 121.8(3) . . ?
N5 C46 C43 116.1(3) . . ?
C47 C46 C43 122.1(3) . . ?
C48 C47 C46 117.5(4) . . ?
C48 C47 C45 124.8(4) . . ?
C46 C47 C45 117.6(4) . . ?
C49 C48 C47 119.9(4) . . ?
C48 C49 C50 119.9(4) . . ?
N5 C50 C49 121.9(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_Compound_4a
_database_code_depnum_ccdc_archive 'CCDC 1477776'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C42 H30 F4 Ir N5 O2'
_chemical_formula_sum            'C42 H30 F4 Ir N5 O2'
_chemical_formula_weight         904.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 '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                   14.8872(7)
_cell_length_b                   16.5821(7)
_cell_length_c                   18.9038(8)
_cell_angle_alpha                93.720(3)
_cell_angle_beta                 104.970(3)
_cell_angle_gamma                96.521(3)
_cell_volume                     4457.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      66.40

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             1784
_exptl_absorpt_coefficient_mu    6.251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.386
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            79873
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.101
_diffrn_reflns_theta_max         66.689
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             15721
_reflns_number_gt                12860
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 The structure contains channels of severely disordered and partially evaporated
 solvent molecules, believed to be pentane for the most part. Our attempts at
 modeling these molecules didn't yield satisfying results. PLATON-SQUEEZE was
 instead used to further refine the structure while accounting for the
 corresponding unassigned electron density.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+1.4316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         15721
_refine_ls_number_parameters     973
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.213
_refine_diff_density_min         -0.891
_refine_diff_density_rms         0.071

# SQUEEZE RESULTS (Version = 160617)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material

_platon_squeeze_void_average_x   0.000
_platon_squeeze_void_average_y   0.007
_platon_squeeze_void_average_z   -0.002
_platon_squeeze_void_volume      1283
_platon_squeeze_void_count_electrons 265
_platon_squeeze_void_probe_radius 1.20

# Missing Reflections Below sin(th)/lambda = 0.25

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 1 0 2.695
0 0 1 2.431

_platon_squeeze_details          
;
TITL shelx     P -1         R = 0.04
CELL   14.8872   16.5821   18.9038     93.72    104.97     96.52
SPGR P-1
C101 0.030 0.556 0.473 !       2.56 eA-3
C102 0.281 0.696 0.253 !       1.91 eA-3
C103 0.105 0.650 0.436 !       1.86 eA-3
C104 0.256 0.723 0.185 !       1.48 eA-3
C105 0.033 0.628 0.433 !       1.46 eA-3
C106 0.013 0.543 0.252 !       1.36 eA-3
Q107 0.640 0.312 0.328 !       1.33 eA-3
C108 0.054 0.556 0.305 !       1.28 eA-3
C109 0.015 0.992 0.025 !       1.25 eA-3
C110 0.889 0.470 0.075 !       1.23 eA-3
C111 0.080 0.960 0.073 !       1.22 eA-3
C112 0.087 0.929 0.081 !       1.21 eA-3
C113 0.076 0.904 0.110 !       1.21 eA-3
C114 0.864 0.440 0.042 !       1.20 eA-3
C115 0.044 0.648 0.337 !       1.16 eA-3
C116 0.965 0.504 0.169 !       1.13 eA-3
C117 0.023 0.946 0.081 !       1.09 eA-3
C118 0.037 0.914 0.102 !       1.07 eA-3
C119 0.934 0.484 0.126 !       1.07 eA-3
C120 0.955 0.466 0.146 !       1.04 eA-3
C121 0.045 0.924 0.032 !       1.00 eA-3
Q122 0.488 0.340 0.294 !       0.97 eA-3
Q123 0.575 0.345 0.309 !       0.94 eA-3
C124 0.903 0.389 0.082 !       0.92 eA-3
Q125 0.499 0.827 0.440 !       0.89 eA-3
C126 0.880 0.416 0.016 !       0.87 eA-3
C127 0.133 0.734 0.156 !       0.86 eA-3
C128 0.186 0.542 0.021 !       0.85 eA-3
C129 0.143 0.683 0.246 !       0.85 eA-3
C130 0.914 0.432 0.138 !       0.83 eA-3
C131 0.110 0.627 0.237 !       0.82 eA-3
Q132 0.714 0.343 0.062 !       0.80 eA-3
C133 0.146 0.657 0.205 !       0.80 eA-3
C134 0.861 0.328 0.105 !       0.80 eA-3
C135 0.884 0.570 0.045 !       0.80 eA-3
Q136 0.639 0.830 0.191 !       0.79 eA-3
Q137 0.566 0.809 0.177 !       0.79 eA-3
C138 0.173 0.661 0.078 !       0.76 eA-3
Q139 0.720 0.832 0.186 !       0.75 eA-3
C140 0.932 0.562 0.091 !       0.75 eA-3
C141 0.143 0.707 0.105 !       0.74 eA-3
C142 0.953 0.682 0.040 !       0.73 eA-3
C143 0.174 0.797 0.153 !       0.73 eA-3
C144 0.186 0.607 0.052 !       0.69 eA-3
C145 0.897 0.644 0.009 !       0.69 eA-3
Q146 0.623 0.821 0.247 !       0.67 eA-3
C147 0.105 0.610 0.315 !       0.67 eA-3
Q148 0.684 0.833 0.123 !       0.66 eA-3
Q149 0.715 0.815 0.239 !       0.65 eA-3
Q150 0.499 0.332 0.345 !       0.64 eA-3
C151 0.132 0.661 0.033 !       0.64 eA-3
Q152 0.568 0.856 0.139 !       0.64 eA-3
C153 0.917 0.612 0.037 !       0.63 eA-3
C154 0.136 0.426 0.016 !       0.63 eA-3
C155 0.953 0.735 0.025 !       0.62 eA-3
C156 0.982 0.564 0.130 !       0.62 eA-3
C157 0.999 0.539 0.124 !       0.61 eA-3
Q158 0.361 0.873 0.405 !       0.61 eA-3
C159 0.045 0.679 0.012 !       0.60 eA-3
Q160 0.577 0.342 0.247 !       0.60 eA-3
Q161 0.622 0.298 0.287 !       0.60 eA-3
Q162 0.575 0.347 0.374 !       0.58 eA-3
C163 0.009 0.779 0.064 !       0.58 eA-3
C164 0.088 0.786 0.095 !       0.57 eA-3
Q165 0.153 1.007 0.314 !       0.54 eA-3
C166 0.982 0.531 0.067 !       0.53 eA-3
C167 0.245 0.663 0.077 !       0.53 eA-3
C168 0.922 0.093 0.027 !       0.52 eA-3
C169 1.001 0.717 0.028 !       0.52 eA-3
C170 0.066 0.556 0.014 !       0.51 eA-3
C171 0.085 0.688 0.124 !       0.50 eA-3
C172 0.866 0.335 0.154 !       0.50 eA-3
C173 0.981 0.624 0.035 !       0.50 eA-3
C174 0.015 0.337 0.003 !       0.50 eA-3
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.56710(2) 0.32981(2) 0.30911(2) 0.03343(5) Uani 1 1 d . . . . .
Ir2 Ir 0.36061(2) 0.16586(2) 0.81583(2) 0.03268(5) Uani 1 1 d . . . . .
F1 F 0.74153(19) 0.56444(14) 0.19633(14) 0.0726(7) Uani 1 1 d . . . . .
F2 F 0.7462(2) 0.62745(14) 0.44174(15) 0.0825(8) Uani 1 1 d . . . . .
F3 F 0.3171(2) 0.45920(17) 0.42114(18) 0.0890(9) Uani 1 1 d . . . . .
F4 F 0.25508(19) 0.45843(18) 0.16655(18) 0.0929(9) Uani 1 1 d . . . . .
F5 F 0.3601(2) 0.39501(17) 1.02441(17) 0.1023(11) Uani 1 1 d . . . . .
F6 F 0.2072(2) 0.14201(18) 1.04903(14) 0.0909(9) Uani 1 1 d . . . . .
F7 F 0.5271(2) -0.08209(13) 0.92379(14) 0.0733(7) Uani 1 1 d . . . . .
F8 F 0.71940(18) 0.16732(17) 0.98197(15) 0.0813(8) Uani 1 1 d . . . . .
O1 O 1.09341(18) 0.16028(17) 0.43193(15) 0.0574(7) Uani 1 1 d . . . . .
O2 O 0.96692(18) 0.38093(15) 0.34067(17) 0.0607(7) Uani 1 1 d . . . . .
O3 O 0.5893(2) 0.0827(2) 0.45811(16) 0.0729(9) Uani 1 1 d . . . . .
O4 O 0.66277(17) 0.07463(16) 0.70492(14) 0.0515(6) Uani 1 1 d . . . . .
N1 N 0.58539(19) 0.15554(14) 0.30968(14) 0.0337(6) Uani 1 1 d . . . . .
N2 N 0.43737(19) 0.15647(15) 0.26344(15) 0.0366(6) Uani 1 1 d . . . . .
N3 N 1.03002(19) 0.26816(18) 0.38215(17) 0.0448(7) Uani 1 1 d . . . . .
N4 N 0.5788(2) 0.33682(15) 0.20437(15) 0.0368(6) Uani 1 1 d . . . . .
N5 N 0.5561(2) 0.33897(16) 0.41570(16) 0.0415(7) Uani 1 1 d . . . . .
N6 N 0.25475(18) 0.18159(14) 0.66313(14) 0.0325(6) Uani 1 1 d . . . . .
N7 N 0.1607(2) 0.20860(16) 0.72854(16) 0.0402(7) Uani 1 1 d . . . . .
N8 N 0.6243(2) 0.07514(19) 0.58083(17) 0.0469(7) Uani 1 1 d . . . . .
N9 N 0.4220(2) 0.28509(15) 0.83470(15) 0.0385(6) Uani 1 1 d . . . . .
N10 N 0.3060(2) 0.04579(15) 0.81465(14) 0.0372(6) Uani 1 1 d . . . . .
C1 C 0.5177(2) 0.20683(18) 0.29425(17) 0.0332(7) Uani 1 1 d . . . . .
C2 C 0.4539(3) 0.07606(19) 0.25751(19) 0.0422(8) Uani 1 1 d . . . . .
H2 H 0.408307 0.029916 0.237222 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5458(2) 0.07551(19) 0.28561(19) 0.0399(8) Uani 1 1 d . . . . .
H3 H 0.577968 0.029027 0.288563 0.048 Uiso 1 1 calc R U . . .
C4 C 0.6915(2) 0.27605(18) 0.33152(18) 0.0345(7) Uani 1 1 d . . . . .
C5 C 0.6806(2) 0.19199(18) 0.33555(18) 0.0349(7) Uani 1 1 d . . . . .
C6 C 0.7562(2) 0.14749(18) 0.36251(17) 0.0345(7) Uani 1 1 d . . . . .
C7 C 0.8483(2) 0.18949(19) 0.37268(17) 0.0369(7) Uani 1 1 d . . . . .
C8 C 0.8599(2) 0.27105(19) 0.35763(18) 0.0376(7) Uani 1 1 d . . . . .
C9 C 0.7838(2) 0.31363(19) 0.34192(18) 0.0379(8) Uani 1 1 d . . . . .
H9 H 0.794405 0.370545 0.337991 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7484(2) 0.06656(19) 0.38346(19) 0.0393(8) Uani 1 1 d . . . . .
H10 H 0.688081 0.037584 0.379175 0.047 Uiso 1 1 calc R U . . .
C11 C 0.8270(3) 0.0299(2) 0.4098(2) 0.0449(8) Uani 1 1 d . . . . .
H11 H 0.820000 -0.024277 0.422986 0.054 Uiso 1 1 calc R U . . .
C12 C 0.9171(3) 0.0706(2) 0.41762(19) 0.0444(8) Uani 1 1 d . . . . .
H12 H 0.970703 0.044132 0.435528 0.053 Uiso 1 1 calc R U . . .
C13 C 0.9272(2) 0.1491(2) 0.39910(17) 0.0385(8) Uani 1 1 d . . . . .
C14 C 1.0228(3) 0.1911(2) 0.40647(19) 0.0445(8) Uani 1 1 d . . . . .
C15 C 0.9541(2) 0.3125(2) 0.3595(2) 0.0442(8) Uani 1 1 d . . . . .
C16 C 0.3450(3) 0.1823(2) 0.2386(2) 0.0520(9) Uani 1 1 d . . . . .
H16A H 0.298149 0.134396 0.218308 0.078 Uiso 1 1 calc R U . . .
H16B H 0.329367 0.210125 0.280294 0.078 Uiso 1 1 calc R U . . .
H16C H 0.345371 0.219608 0.200561 0.078 Uiso 1 1 calc R U . . .
C17 C 1.1235(3) 0.3047(2) 0.3774(2) 0.0533(10) Uani 1 1 d . . . . .
H17A H 1.171602 0.296065 0.422356 0.064 Uiso 1 1 calc R U . . .
H17B H 1.124163 0.364208 0.374934 0.064 Uiso 1 1 calc R U . . .
C18 C 1.1476(3) 0.2677(3) 0.3105(2) 0.0627(11) Uani 1 1 d . . . . .
H18A H 1.212076 0.291331 0.311438 0.075 Uiso 1 1 calc R U . . .
H18B H 1.147523 0.208326 0.313930 0.075 Uiso 1 1 calc R U . . .
C19 C 1.0825(4) 0.2803(4) 0.2382(3) 0.0935(17) Uani 1 1 d . . . . .
H19A H 1.082100 0.339529 0.234521 0.112 Uiso 1 1 calc R U . . .
H19B H 1.018061 0.255916 0.236592 0.112 Uiso 1 1 calc R U . . .
C20 C 1.1100(5) 0.2426(6) 0.1721(4) 0.144(3) Uani 1 1 d . . . . .
H20A H 1.065336 0.252683 0.126552 0.216 Uiso 1 1 calc R U . . .
H20B H 1.173253 0.267400 0.172708 0.216 Uiso 1 1 calc R U . . .
H20C H 1.109187 0.183751 0.174779 0.216 Uiso 1 1 calc R U . . .
C21 C 0.6383(2) 0.44457(18) 0.31913(19) 0.0376(8) Uani 1 1 d . . . . .
C22 C 0.6677(3) 0.5004(2) 0.3826(2) 0.0494(9) Uani 1 1 d . . . . .
H22 H 0.652368 0.487347 0.426594 0.059 Uiso 1 1 calc R U . . .
C23 C 0.7187(3) 0.5738(2) 0.3800(2) 0.0563(10) Uani 1 1 d . . . . .
C24 C 0.7437(3) 0.5968(2) 0.3185(2) 0.0576(11) Uani 1 1 d . . . . .
H24 H 0.778576 0.648377 0.318326 0.069 Uiso 1 1 calc R U . . .
C25 C 0.7157(3) 0.5412(2) 0.2569(2) 0.0504(9) Uani 1 1 d . . . . .
C26 C 0.6633(2) 0.46565(19) 0.2548(2) 0.0409(8) Uani 1 1 d . . . . .
C27 C 0.6313(3) 0.4043(2) 0.1915(2) 0.0417(8) Uani 1 1 d . . . . .
C28 C 0.6489(3) 0.4086(2) 0.1228(2) 0.0556(10) Uani 1 1 d . . . . .
H28 H 0.686460 0.455169 0.114012 0.067 Uiso 1 1 calc R U . . .
C29 C 0.6124(3) 0.3464(3) 0.0677(2) 0.0636(12) Uani 1 1 d . . . . .
H29 H 0.624636 0.349840 0.021057 0.076 Uiso 1 1 calc R U . . .
C30 C 0.5579(3) 0.2789(2) 0.0806(2) 0.0532(10) Uani 1 1 d . . . . .
H30 H 0.531675 0.235319 0.043140 0.064 Uiso 1 1 calc R U . . .
C31 C 0.5429(3) 0.2764(2) 0.14863(19) 0.0429(8) Uani 1 1 d . . . . .
H31 H 0.505215 0.230023 0.157568 0.051 Uiso 1 1 calc R U . . .
C32 C 0.4438(2) 0.38043(19) 0.2951(2) 0.0417(8) Uani 1 1 d . . . . .
C33 C 0.3869(3) 0.4014(2) 0.2296(2) 0.0492(9) Uani 1 1 d . . . . .
H33 H 0.401074 0.389494 0.184141 0.059 Uiso 1 1 calc R U . . .
C34 C 0.3106(3) 0.4392(2) 0.2318(3) 0.0655(12) Uani 1 1 d . . . . .
C35 C 0.2865(3) 0.4604(3) 0.2956(3) 0.0702(13) Uani 1 1 d . . . . .
H35 H 0.233994 0.488065 0.295383 0.084 Uiso 1 1 calc R U . . .
C36 C 0.3422(3) 0.4395(2) 0.3584(3) 0.0596(11) Uani 1 1 d . . . . .
C37 C 0.4209(3) 0.3998(2) 0.3622(2) 0.0487(9) Uani 1 1 d . . . . .
C38 C 0.4820(3) 0.3758(2) 0.4281(2) 0.0494(10) Uani 1 1 d . . . . .
C39 C 0.4729(3) 0.3846(3) 0.4997(3) 0.0650(12) Uani 1 1 d . . . . .
H39 H 0.422111 0.409388 0.508952 0.078 Uiso 1 1 calc R U . . .
C40 C 0.5362(4) 0.3580(3) 0.5569(3) 0.0734(14) Uani 1 1 d . . . . .
H40 H 0.529059 0.364097 0.605383 0.088 Uiso 1 1 calc R U . . .
C41 C 0.6099(4) 0.3224(3) 0.5434(2) 0.0677(12) Uani 1 1 d . . . . .
H41 H 0.654705 0.304010 0.582413 0.081 Uiso 1 1 calc R U . . .
C42 C 0.6174(3) 0.3139(2) 0.4723(2) 0.0531(10) Uani 1 1 d . . . . .
H42 H 0.668358 0.289285 0.463043 0.064 Uiso 1 1 calc R U . . .
C43 C 0.2487(2) 0.19223(17) 0.73453(18) 0.0355(7) Uani 1 1 d . . . . .
C44 C 0.1116(2) 0.2061(2) 0.6554(2) 0.0445(8) Uani 1 1 d . . . . .
H44 H 0.048342 0.215451 0.637413 0.053 Uiso 1 1 calc R U . . .
C45 C 0.1689(2) 0.18818(19) 0.61448(19) 0.0387(8) Uani 1 1 d . . . . .
H45 H 0.153824 0.181281 0.562272 0.046 Uiso 1 1 calc R U . . .
C46 C 0.4028(2) 0.14476(17) 0.71918(17) 0.0316(7) Uani 1 1 d . . . . .
C47 C 0.3424(2) 0.16054(17) 0.65340(17) 0.0308(7) Uani 1 1 d . . . . .
C48 C 0.3662(2) 0.16067(17) 0.58524(17) 0.0317(7) Uani 1 1 d . . . . .
C49 C 0.4531(2) 0.13322(18) 0.58391(17) 0.0329(7) Uani 1 1 d . . . . .
C50 C 0.5147(2) 0.11512(18) 0.65015(17) 0.0334(7) Uani 1 1 d . . . . .
C51 C 0.4906(2) 0.12334(17) 0.71477(17) 0.0326(7) Uani 1 1 d . . . . .
H51 H 0.534747 0.114284 0.758788 0.039 Uiso 1 1 calc R U . . .
C52 C 0.3138(3) 0.1874(2) 0.51919(18) 0.0402(8) Uani 1 1 d . . . . .
H52 H 0.257111 0.208834 0.518639 0.048 Uiso 1 1 calc R U . . .
C53 C 0.3430(3) 0.1832(2) 0.4561(2) 0.0480(9) Uani 1 1 d . . . . .
H53 H 0.306939 0.202276 0.412916 0.058 Uiso 1 1 calc R U . . .
C54 C 0.4250(3) 0.1512(2) 0.45486(19) 0.0471(9) Uani 1 1 d . . . . .
H54 H 0.443014 0.146084 0.410249 0.056 Uiso 1 1 calc R U . . .
C55 C 0.4799(2) 0.1270(2) 0.51762(19) 0.0401(8) Uani 1 1 d . . . . .
C56 C 0.5672(3) 0.0942(2) 0.5150(2) 0.0489(9) Uani 1 1 d . . . . .
C57 C 0.6057(2) 0.0879(2) 0.6493(2) 0.0411(8) Uani 1 1 d . . . . .
C58 C 0.1220(3) 0.2279(3) 0.7903(2) 0.0576(10) Uani 1 1 d . . . . .
H58A H 0.056703 0.237356 0.771548 0.086 Uiso 1 1 calc R U . . .
H58B H 0.124633 0.182181 0.820807 0.086 Uiso 1 1 calc R U . . .
H58C H 0.158912 0.277059 0.819957 0.086 Uiso 1 1 calc R U . . .
C59 C 0.7109(3) 0.0389(2) 0.5795(2) 0.0562(10) Uani 1 1 d . . . . .
H59A H 0.700447 0.006365 0.531533 0.067 Uiso 1 1 calc R U . . .
H59B H 0.723287 0.001362 0.618471 0.067 Uiso 1 1 calc R U . . .
C60 C 0.7948(3) 0.1013(3) 0.5906(3) 0.0741(13) Uani 1 1 d . . . . .
H60A H 0.799644 0.140288 0.633789 0.089 Uiso 1 1 calc R U . . .
H60B H 0.788866 0.132022 0.546853 0.089 Uiso 1 1 calc R U . . .
C61 C 0.8841(3) 0.0581(4) 0.6033(3) 0.0909(17) Uani 1 1 d . . . . .
H61A H 0.870764 0.008552 0.568089 0.109 Uiso 1 1 calc R U . . .
H61B H 0.935073 0.094931 0.592604 0.109 Uiso 1 1 calc R U . . .
C62 C 0.9177(4) 0.0339(5) 0.6809(3) 0.121(2) Uani 1 1 d . . . . .
H62A H 0.974001 0.007055 0.685217 0.182 Uiso 1 1 calc R U . . .
H62B H 0.932637 0.082719 0.716126 0.182 Uiso 1 1 calc R U . . .
H62C H 0.868266 -0.003743 0.691588 0.182 Uiso 1 1 calc R U . . .
C63 C 0.3230(2) 0.2017(2) 0.90997(18) 0.0407(8) Uani 1 1 d . . . . .
C64 C 0.2727(3) 0.1546(2) 0.94919(19) 0.0477(9) Uani 1 1 d . . . . .
H64 H 0.251019 0.098620 0.933155 0.057 Uiso 1 1 calc R U . . .
C65 C 0.2547(3) 0.1892(3) 1.0104(2) 0.0614(11) Uani 1 1 d . . . . .
C66 C 0.2829(3) 0.2694(3) 1.0369(2) 0.0743(14) Uani 1 1 d . . . . .
H66 H 0.268974 0.292051 1.079678 0.089 Uiso 1 1 calc R U . . .
C67 C 0.3322(3) 0.3152(3) 0.9982(2) 0.0634(12) Uani 1 1 d . . . . .
C68 C 0.3549(3) 0.2842(2) 0.93633(19) 0.0462(9) Uani 1 1 d . . . . .
C69 C 0.4119(3) 0.3292(2) 0.8953(2) 0.0457(9) Uani 1 1 d . . . . .
C70 C 0.4577(3) 0.4089(2) 0.9138(2) 0.0595(11) Uani 1 1 d . . . . .
H70 H 0.453150 0.439327 0.956769 0.071 Uiso 1 1 calc R U . . .
C71 C 0.5092(3) 0.4437(2) 0.8705(2) 0.0656(12) Uani 1 1 d . . . . .
H71 H 0.539617 0.498262 0.883016 0.079 Uiso 1 1 calc R U . . .
C72 C 0.5164(3) 0.3991(2) 0.8089(2) 0.0590(11) Uani 1 1 d . . . . .
H72 H 0.551843 0.422114 0.778163 0.071 Uiso 1 1 calc R U . . .
C73 C 0.4718(3) 0.3210(2) 0.7928(2) 0.0502(9) Uani 1 1 d . . . . .
H73 H 0.476197 0.290544 0.749727 0.060 Uiso 1 1 calc R U . . .
C74 C 0.4754(3) 0.1227(2) 0.87975(18) 0.0411(8) Uani 1 1 d . . . . .
C75 C 0.5643(3) 0.1652(2) 0.91277(18) 0.0432(8) Uani 1 1 d . . . . .
H75 H 0.575840 0.222336 0.910313 0.052 Uiso 1 1 calc R U . . .
C76 C 0.6347(3) 0.1246(3) 0.9487(2) 0.0548(10) Uani 1 1 d . . . . .
C77 C 0.6239(3) 0.0417(3) 0.9531(2) 0.0597(11) Uani 1 1 d . . . . .
H77 H 0.674470 0.014711 0.977497 0.072 Uiso 1 1 calc R U . . .
C78 C 0.5371(3) 0.0004(2) 0.9207(2) 0.0512(10) Uani 1 1 d . . . . .
C79 C 0.4609(3) 0.0373(2) 0.88533(18) 0.0423(8) Uani 1 1 d . . . . .
C80 C 0.3660(3) -0.0035(2) 0.85199(18) 0.0421(8) Uani 1 1 d . . . . .
C81 C 0.3311(3) -0.0845(2) 0.8566(2) 0.0551(10) Uani 1 1 d . . . . .
H81 H 0.372213 -0.119338 0.881944 0.066 Uiso 1 1 calc R U . . .
C82 C 0.2391(4) -0.1142(2) 0.8251(2) 0.0623(12) Uani 1 1 d . . . . .
H82 H 0.216256 -0.169321 0.828243 0.075 Uiso 1 1 calc R U . . .
C83 C 0.1796(3) -0.0634(2) 0.7886(2) 0.0533(10) Uani 1 1 d . . . . .
H83 H 0.114990 -0.082497 0.767094 0.064 Uiso 1 1 calc R U . . .
C84 C 0.2156(3) 0.0155(2) 0.78418(19) 0.0449(8) Uani 1 1 d . . . . .
H84 H 0.174768 0.050183 0.758344 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N4 2.041(3) . ?
Ir1 C21 2.043(3) . ?
Ir1 N5 2.061(3) . ?
Ir1 C1 2.063(3) . ?
Ir1 C32 2.067(3) . ?
Ir1 C4 2.103(3) . ?
Ir2 N9 2.049(3) . ?
Ir2 C74 2.054(4) . ?
Ir2 N10 2.060(3) . ?
Ir2 C43 2.064(3) . ?
Ir2 C63 2.070(3) . ?
Ir2 C46 2.101(3) . ?
F1 C25 1.364(4) . ?
F2 C23 1.362(4) . ?
F3 C36 1.365(5) . ?
F4 C34 1.375(5) . ?
F5 C67 1.362(5) . ?
F6 C65 1.364(5) . ?
F7 C78 1.366(4) . ?
F8 C76 1.348(5) . ?
O1 C14 1.221(4) . ?
O2 C15 1.221(4) . ?
O3 C56 1.213(4) . ?
O4 C57 1.220(4) . ?
N1 C1 1.378(4) . ?
N1 C3 1.386(4) . ?
N1 C5 1.422(4) . ?
N2 C1 1.348(4) . ?
N2 C2 1.386(4) . ?
N2 C16 1.456(4) . ?
N3 C14 1.388(5) . ?
N3 C15 1.407(5) . ?
N3 C17 1.480(5) . ?
N4 C31 1.360(4) . ?
N4 C27 1.363(4) . ?
N5 C42 1.338(5) . ?
N5 C38 1.382(5) . ?
N6 C43 1.377(4) . ?
N6 C45 1.389(4) . ?
N6 C47 1.441(4) . ?
N7 C43 1.346(4) . ?
N7 C44 1.382(5) . ?
N7 C58 1.462(4) . ?
N8 C56 1.392(5) . ?
N8 C57 1.400(4) . ?
N8 C59 1.488(5) . ?
N9 C73 1.341(5) . ?
N9 C69 1.369(4) . ?
N10 C84 1.343(5) . ?
N10 C80 1.370(4) . ?
C2 C3 1.335(5) . ?
C4 C5 1.394(4) . ?
C4 C9 1.402(5) . ?
C5 C6 1.419(5) . ?
C6 C10 1.424(4) . ?
C6 C7 1.426(5) . ?
C7 C8 1.401(4) . ?
C7 C13 1.412(5) . ?
C8 C9 1.380(5) . ?
C8 C15 1.481(5) . ?
C10 C11 1.374(5) . ?
C11 C12 1.398(5) . ?
C12 C13 1.373(5) . ?
C13 C14 1.479(5) . ?
C17 C18 1.513(6) . ?
C18 C19 1.500(6) . ?
C19 C20 1.529(8) . ?
C21 C22 1.407(5) . ?
C21 C26 1.414(5) . ?
C22 C23 1.371(5) . ?
C23 C24 1.373(6) . ?
C24 C25 1.378(6) . ?
C25 C26 1.390(5) . ?
C26 C27 1.461(5) . ?
C27 C28 1.393(5) . ?
C28 C29 1.373(6) . ?
C29 C30 1.379(6) . ?
C30 C31 1.364(5) . ?
C32 C33 1.397(5) . ?
C32 C37 1.421(5) . ?
C33 C34 1.367(5) . ?
C34 C35 1.378(7) . ?
C35 C36 1.352(7) . ?
C36 C37 1.396(5) . ?
C37 C38 1.448(6) . ?
C38 C39 1.395(6) . ?
C39 C40 1.371(7) . ?
C40 C41 1.374(7) . ?
C41 C42 1.378(6) . ?
C44 C45 1.334(5) . ?
C46 C47 1.394(4) . ?
C46 C51 1.414(4) . ?
C47 C48 1.422(4) . ?
C48 C52 1.419(5) . ?
C48 C49 1.424(4) . ?
C49 C55 1.411(5) . ?
C49 C50 1.420(5) . ?
C50 C51 1.362(4) . ?
C50 C57 1.480(5) . ?
C52 C53 1.371(5) . ?
C53 C54 1.390(5) . ?
C54 C55 1.368(5) . ?
C55 C56 1.475(5) . ?
C59 C60 1.489(6) . ?
C60 C61 1.552(7) . ?
C61 C62 1.520(8) . ?
C63 C64 1.396(5) . ?
C63 C68 1.410(5) . ?
C64 C65 1.360(5) . ?
C65 C66 1.369(6) . ?
C66 C67 1.368(6) . ?
C67 C68 1.383(5) . ?
C68 C69 1.467(5) . ?
C69 C70 1.395(5) . ?
C70 C71 1.368(6) . ?
C71 C72 1.375(6) . ?
C72 C73 1.364(5) . ?
C74 C75 1.393(5) . ?
C74 C79 1.423(5) . ?
C75 C76 1.367(5) . ?
C76 C77 1.376(6) . ?
C77 C78 1.360(6) . ?
C78 C79 1.388(5) . ?
C79 C80 1.456(5) . ?
C80 C81 1.401(5) . ?
C81 C82 1.364(6) . ?
C82 C83 1.378(6) . ?
C83 C84 1.372(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
N4 Ir1 C21 79.56(12) . . ?
N4 Ir1 N5 172.56(10) . . ?
C21 Ir1 N5 93.83(12) . . ?
N4 Ir1 C1 95.20(11) . . ?
C21 Ir1 C1 168.96(12) . . ?
N5 Ir1 C1 91.89(11) . . ?
N4 Ir1 C32 96.90(13) . . ?
C21 Ir1 C32 88.90(13) . . ?
N5 Ir1 C32 79.45(14) . . ?
C1 Ir1 C32 101.44(13) . . ?
N4 Ir1 C4 87.55(11) . . ?
C21 Ir1 C4 92.58(12) . . ?
N5 Ir1 C4 96.20(12) . . ?
C1 Ir1 C4 77.40(12) . . ?
C32 Ir1 C4 175.50(13) . . ?
N9 Ir2 C74 94.27(13) . . ?
N9 Ir2 N10 170.93(10) . . ?
C74 Ir2 N10 79.81(13) . . ?
N9 Ir2 C43 92.36(11) . . ?
C74 Ir2 C43 167.99(12) . . ?
N10 Ir2 C43 94.70(12) . . ?
N9 Ir2 C63 79.81(12) . . ?
C74 Ir2 C63 89.56(13) . . ?
N10 Ir2 C63 93.18(12) . . ?
C43 Ir2 C63 101.47(13) . . ?
N9 Ir2 C46 93.45(11) . . ?
C74 Ir2 C46 92.79(12) . . ?
N10 Ir2 C46 93.71(10) . . ?
C43 Ir2 C46 76.81(12) . . ?
C63 Ir2 C46 173.01(12) . . ?
C1 N1 C3 110.2(3) . . ?
C1 N1 C5 117.5(2) . . ?
C3 N1 C5 131.5(3) . . ?
C1 N2 C2 111.1(3) . . ?
C1 N2 C16 125.1(3) . . ?
C2 N2 C16 123.8(3) . . ?
C14 N3 C15 124.4(3) . . ?
C14 N3 C17 117.5(3) . . ?
C15 N3 C17 118.0(3) . . ?
C31 N4 C27 118.5(3) . . ?
C31 N4 Ir1 124.1(2) . . ?
C27 N4 Ir1 117.2(2) . . ?
C42 N5 C38 119.5(3) . . ?
C42 N5 Ir1 123.8(2) . . ?
C38 N5 Ir1 116.6(3) . . ?
C43 N6 C45 110.0(3) . . ?
C43 N6 C47 116.5(3) . . ?
C45 N6 C47 133.3(3) . . ?
C43 N7 C44 110.5(3) . . ?
C43 N7 C58 125.2(3) . . ?
C44 N7 C58 124.3(3) . . ?
C56 N8 C57 124.0(3) . . ?
C56 N8 C59 118.8(3) . . ?
C57 N8 C59 117.2(3) . . ?
C73 N9 C69 119.1(3) . . ?
C73 N9 Ir2 124.3(2) . . ?
C69 N9 Ir2 116.6(2) . . ?
C84 N10 C80 119.3(3) . . ?
C84 N10 Ir2 124.2(2) . . ?
C80 N10 Ir2 116.4(2) . . ?
N2 C1 N1 104.3(3) . . ?
N2 C1 Ir1 139.3(2) . . ?
N1 C1 Ir1 115.5(2) . . ?
C3 C2 N2 107.2(3) . . ?
C2 C3 N1 107.1(3) . . ?
C5 C4 C9 115.8(3) . . ?
C5 C4 Ir1 115.8(2) . . ?
C9 C4 Ir1 128.4(2) . . ?
C4 C5 C6 123.7(3) . . ?
C4 C5 N1 112.8(3) . . ?
C6 C5 N1 123.6(3) . . ?
C5 C6 C10 125.9(3) . . ?
C5 C6 C7 116.6(3) . . ?
C10 C6 C7 117.4(3) . . ?
C8 C7 C13 120.5(3) . . ?
C8 C7 C6 119.6(3) . . ?
C13 C7 C6 119.8(3) . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 C15 119.6(3) . . ?
C7 C8 C15 120.2(3) . . ?
C8 C9 C4 122.5(3) . . ?
C11 C10 C6 120.8(3) . . ?
C10 C11 C12 121.5(3) . . ?
C13 C12 C11 119.2(3) . . ?
C12 C13 C7 121.2(3) . . ?
C12 C13 C14 118.7(3) . . ?
C7 C13 C14 120.1(3) . . ?
O1 C14 N3 120.1(3) . . ?
O1 C14 C13 122.7(3) . . ?
N3 C14 C13 117.2(3) . . ?
O2 C15 N3 120.3(3) . . ?
O2 C15 C8 122.8(3) . . ?
N3 C15 C8 116.9(3) . . ?
N3 C17 C18 111.5(3) . . ?
C19 C18 C17 114.7(4) . . ?
C18 C19 C20 113.0(5) . . ?
C22 C21 C26 118.9(3) . . ?
C22 C21 Ir1 127.2(3) . . ?
C26 C21 Ir1 113.8(2) . . ?
C23 C22 C21 119.2(4) . . ?
F2 C23 C22 118.5(4) . . ?
F2 C23 C24 117.9(3) . . ?
C22 C23 C24 123.6(4) . . ?
C23 C24 C25 116.7(3) . . ?
F1 C25 C24 116.1(3) . . ?
F1 C25 C26 120.6(3) . . ?
C24 C25 C26 123.2(4) . . ?
C25 C26 C21 118.4(3) . . ?
C25 C26 C27 125.9(3) . . ?
C21 C26 C27 115.7(3) . . ?
N4 C27 C28 119.6(3) . . ?
N4 C27 C26 113.2(3) . . ?
C28 C27 C26 127.2(3) . . ?
C29 C28 C27 120.7(4) . . ?
C28 C29 C30 119.6(4) . . ?
C31 C30 C29 118.1(4) . . ?
N4 C31 C30 123.5(3) . . ?
C33 C32 C37 119.0(3) . . ?
C33 C32 Ir1 127.4(3) . . ?
C37 C32 Ir1 113.5(3) . . ?
C34 C33 C32 119.0(4) . . ?
C33 C34 F4 118.0(4) . . ?
C33 C34 C35 124.1(5) . . ?
F4 C34 C35 117.9(4) . . ?
C36 C35 C34 116.0(4) . . ?
C35 C36 F3 115.7(4) . . ?
C35 C36 C37 124.6(4) . . ?
F3 C36 C37 119.7(4) . . ?
C36 C37 C32 117.3(4) . . ?
C36 C37 C38 126.4(4) . . ?
C32 C37 C38 116.3(3) . . ?
N5 C38 C39 118.5(4) . . ?
N5 C38 C37 113.9(3) . . ?
C39 C38 C37 127.6(4) . . ?
C40 C39 C38 121.1(4) . . ?
C39 C40 C41 119.4(4) . . ?
C40 C41 C42 118.6(5) . . ?
N5 C42 C41 122.8(4) . . ?
N7 C43 N6 104.8(3) . . ?
N7 C43 Ir2 137.7(2) . . ?
N6 C43 Ir2 116.8(2) . . ?
C45 C44 N7 108.0(3) . . ?
C44 C45 N6 106.6(3) . . ?
C47 C46 C51 116.1(3) . . ?
C47 C46 Ir2 117.2(2) . . ?
C51 C46 Ir2 126.4(2) . . ?
C46 C47 C48 124.0(3) . . ?
C46 C47 N6 112.2(3) . . ?
C48 C47 N6 123.6(3) . . ?
C52 C48 C47 126.7(3) . . ?
C52 C48 C49 116.8(3) . . ?
C47 C48 C49 116.5(3) . . ?
C55 C49 C50 119.8(3) . . ?
C55 C49 C48 120.3(3) . . ?
C50 C49 C48 119.8(3) . . ?
C51 C50 C49 120.2(3) . . ?
C51 C50 C57 119.7(3) . . ?
C49 C50 C57 120.0(3) . . ?
C50 C51 C46 122.8(3) . . ?
C53 C52 C48 121.6(3) . . ?
C52 C53 C54 120.6(3) . . ?
C55 C54 C53 120.2(3) . . ?
C54 C55 C49 120.3(3) . . ?
C54 C55 C56 119.1(3) . . ?
C49 C55 C56 120.6(3) . . ?
O3 C56 N8 120.0(3) . . ?
O3 C56 C55 122.4(4) . . ?
N8 C56 C55 117.6(3) . . ?
O4 C57 N8 119.7(3) . . ?
O4 C57 C50 122.7(3) . . ?
N8 C57 C50 117.5(3) . . ?
N8 C59 C60 113.0(3) . . ?
C59 C60 C61 109.2(4) . . ?
C62 C61 C60 113.6(5) . . ?
C64 C63 C68 118.2(3) . . ?
C64 C63 Ir2 128.3(3) . . ?
C68 C63 Ir2 113.5(2) . . ?
C65 C64 C63 119.7(4) . . ?
C64 C65 F6 119.0(4) . . ?
C64 C65 C66 123.8(4) . . ?
F6 C65 C66 117.2(3) . . ?
C67 C66 C65 116.2(4) . . ?
F5 C67 C66 116.2(3) . . ?
F5 C67 C68 120.2(4) . . ?
C66 C67 C68 123.6(4) . . ?
C67 C68 C63 118.5(4) . . ?
C67 C68 C69 125.8(3) . . ?
C63 C68 C69 115.7(3) . . ?
N9 C69 C70 119.1(4) . . ?
N9 C69 C68 114.3(3) . . ?
C70 C69 C68 126.6(3) . . ?
C71 C70 C69 120.6(4) . . ?
C70 C71 C72 119.4(4) . . ?
C73 C72 C71 118.6(4) . . ?
N9 C73 C72 123.2(4) . . ?
C75 C74 C79 118.2(3) . . ?
C75 C74 Ir2 128.1(3) . . ?
C79 C74 Ir2 113.5(3) . . ?
C76 C75 C74 119.9(3) . . ?
F8 C76 C75 118.9(4) . . ?
F8 C76 C77 117.7(4) . . ?
C75 C76 C77 123.4(4) . . ?
C78 C77 C76 116.5(4) . . ?
C77 C78 F7 116.3(4) . . ?
C77 C78 C79 123.8(3) . . ?
F7 C78 C79 119.8(4) . . ?
C78 C79 C74 118.1(4) . . ?
C78 C79 C80 126.1(3) . . ?
C74 C79 C80 115.8(3) . . ?
N10 C80 C81 118.8(4) . . ?
N10 C80 C79 114.2(3) . . ?
C81 C80 C79 127.0(3) . . ?
C82 C81 C80 121.0(4) . . ?
C81 C82 C83 119.4(4) . . ?
C84 C83 C82 118.5(4) . . ?
N10 C84 C83 123.0(4) . . ?


