# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_hhb
_database_code_depnum_ccdc_archive 'CCDC 1584888'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H28 F14 Ir N5 O2 P2'
_chemical_formula_sum            'C48 H28 F14 Ir N5 O2 P2'
_chemical_formula_weight         1226.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   10.7026(8)
_cell_length_b                   23.3672(19)
_cell_length_c                   18.9711(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.879(2)
_cell_angle_gamma                90.00
_cell_volume                     4659.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9848
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2400
_exptl_absorpt_coefficient_mu    3.037
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39465
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.49
_reflns_number_total             10660
_reflns_number_gt                9267
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+142.4294P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10660
_refine_ls_number_parameters     649
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1816
_refine_ls_wR_factor_gt          0.1778
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.201
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C42 C 0.9843(17) 0.4144(7) 0.3527(10) 0.063(5) Uani 1 1 d . . .
H42 H 1.0418 0.3854 0.3482 0.076 Uiso 1 1 calc R . .
Ir1 Ir 0.59584(3) 0.634242(16) 0.203093(18) 0.01384(11) Uani 1 1 d . . .
P1 P 0.7027(2) 0.56132(11) 0.35316(13) 0.0172(5) Uani 1 1 d . . .
P2 P 0.4341(2) 0.56013(11) 0.30561(13) 0.0182(5) Uani 1 1 d . . .
O1 O 0.7300(6) 0.5969(3) 0.2905(3) 0.0146(13) Uani 1 1 d . . .
N1 N 0.6164(8) 0.7037(3) 0.2675(4) 0.0160(16) Uani 1 1 d . . .
F6 F 0.5948(6) 0.7700(3) 0.1362(4) 0.0319(15) Uani 1 1 d . . .
N3 N 0.5739(8) 0.5580(4) 0.1518(4) 0.0168(16) Uani 1 1 d . . .
F5 F 0.4279(6) 0.7778(3) 0.1822(4) 0.0327(15) Uani 1 1 d . . .
F11 F 0.4993(8) 0.7789(3) 0.4055(4) 0.045(2) Uani 1 1 d . . .
F7 F 0.6578(6) 0.6208(4) 0.0324(4) 0.042(2) Uani 1 1 d . . .
F9 F 0.7942(8) 0.5559(3) 0.0824(4) 0.0438(19) Uani 1 1 d . . .
F8 F 0.8458(7) 0.6167(3) 0.0082(3) 0.0386(18) Uani 1 1 d . . .
F4 F 0.4302(7) 0.8122(3) 0.0777(4) 0.044(2) Uani 1 1 d . . .
N2 N 0.7755(9) 0.7680(4) 0.3256(5) 0.0220(18) Uani 1 1 d . . .
C1 C 0.8312(11) 0.6503(5) 0.4323(6) 0.025(2) Uani 1 1 d . . .
H1 H 0.8715 0.6553 0.3934 0.029 Uiso 1 1 calc R . .
C2 C 0.8122(9) 0.7083(4) 0.2264(5) 0.0168(19) Uani 1 1 d . . .
C3 C 0.7731(13) 0.4487(5) 0.3359(6) 0.033(3) Uani 1 1 d . . .
H3 H 0.6865 0.4416 0.3219 0.040 Uiso 1 1 calc R . .
C4 C 0.7548(9) 0.6664(4) 0.1755(5) 0.0154(18) Uani 1 1 d . . .
F10 F 0.6579(8) 0.4101(3) 0.1634(4) 0.047(2) Uani 1 1 d . . .
C5 C 0.4840(14) 0.4575(6) 0.0922(6) 0.039(3) Uani 1 1 d . . .
H5 H 0.4523 0.4225 0.0732 0.046 Uiso 1 1 calc R . .
C6 C 0.6818(10) 0.6000(5) 0.4892(5) 0.022(2) Uani 1 1 d . . .
H6 H 0.6222 0.5710 0.4890 0.026 Uiso 1 1 calc R . .
C7 C 0.7445(10) 0.6065(4) 0.4314(5) 0.0181(19) Uani 1 1 d . . .
C8 C 0.4670(9) 0.6579(5) 0.1164(5) 0.019(2) Uani 1 1 d . . .
C9 C 0.4090(10) 0.6092(5) 0.0784(5) 0.022(2) Uani 1 1 d . . .
C10 C 0.9496(9) 0.6741(5) 0.1261(5) 0.021(2) Uani 1 1 d . . .
H10 H 0.9964 0.6627 0.0919 0.025 Uiso 1 1 calc R . .
C11 C 0.8590(11) 0.6871(5) 0.4908(6) 0.030(2) Uani 1 1 d . . .
H11 H 0.9202 0.7155 0.4921 0.036 Uiso 1 1 calc R . .
F3 F 0.1789(8) 0.6985(5) -0.1201(4) 0.066(3) Uani 1 1 d . . .
C12 C 0.8269(9) 0.6523(4) 0.1229(5) 0.0182(19) Uani 1 1 d . . .
C13 C 0.3072(10) 0.6140(6) 0.0208(5) 0.027(2) Uani 1 1 d . . .
H13 H 0.2694 0.5810 -0.0010 0.032 Uiso 1 1 calc R . .
C14 C 0.5764(11) 0.7618(5) 0.3620(6) 0.026(2) Uani 1 1 d . . .
N4 N 0.4217(10) 0.5049(4) 0.0698(5) 0.031(2) Uani 1 1 d . . .
C15 C 0.7331(9) 0.7283(4) 0.2766(5) 0.0148(18) Uani 1 1 d . . .
F2 F 0.1045(9) 0.6207(4) -0.0899(5) 0.074(3) Uani 1 1 d . . .
C16 C 0.4672(10) 0.5540(5) 0.1000(5) 0.023(2) Uani 1 1 d . . .
N5 N 0.5643(8) 0.5344(4) 0.3472(4) 0.0221(18) Uani 1 1 d . . .
C17 C 0.8129(10) 0.5023(5) 0.3616(5) 0.024(2) Uani 1 1 d . . .
C18 C 0.7100(11) 0.6376(5) 0.5473(6) 0.028(2) Uani 1 1 d . . .
H18 H 0.6703 0.6331 0.5865 0.034 Uiso 1 1 calc R . .
C19 C 0.3394(10) 0.5852(5) 0.3687(5) 0.023(2) Uani 1 1 d . . .
C20 C 0.4191(9) 0.7111(5) 0.0869(6) 0.024(2) Uani 1 1 d . . .
C21 C 1.0025(10) 0.7123(4) 0.1789(5) 0.020(2) Uani 1 1 d . . .
C22 C 0.4675(10) 0.7663(5) 0.1208(6) 0.025(2) Uani 1 1 d . . .
C23 C 0.6966(11) 0.7843(5) 0.3696(6) 0.029(2) Uani 1 1 d . . .
H23 H 0.7240 0.8111 0.4055 0.035 Uiso 1 1 calc R . .
C24 C 0.3424(10) 0.5013(5) 0.2597(5) 0.022(2) Uani 1 1 d . . .
C25 C 0.3509(12) 0.5577(6) 0.4360(6) 0.032(3) Uani 1 1 d . . .
H25 H 0.4084 0.5278 0.4478 0.038 Uiso 1 1 calc R . .
C26 C 0.5368(11) 0.7210(5) 0.3108(6) 0.024(2) Uani 1 1 d . . .
H26 H 0.4558 0.7052 0.3059 0.029 Uiso 1 1 calc R . .
C27 C 0.3698(11) 0.4454(5) 0.2821(6) 0.030(2) Uani 1 1 d . . .
H27 H 0.4386 0.4377 0.3188 0.035 Uiso 1 1 calc R . .
C28 C 0.1525(12) 0.6706(6) -0.0648(6) 0.036(3) Uani 1 1 d . . .
C29 C 0.2628(10) 0.6655(6) -0.0038(6) 0.029(3) Uani 1 1 d . . .
F1 F 0.0550(8) 0.6983(6) -0.0457(5) 0.077(4) Uani 1 1 d . . .
C30 C 0.3195(10) 0.7145(5) 0.0282(6) 0.027(2) Uani 1 1 d . . .
H30 H 0.2907 0.7502 0.0103 0.032 Uiso 1 1 calc R . .
C31 C 0.5938(12) 0.4584(5) 0.1425(6) 0.031(3) Uani 1 1 d . . .
C32 C 0.9317(9) 0.7301(4) 0.2288(5) 0.0168(19) Uani 1 1 d . . .
H32 H 0.9650 0.7567 0.2637 0.020 Uiso 1 1 calc R . .
C33 C 0.1907(12) 0.4130(6) 0.1943(7) 0.038(3) Uani 1 1 d . . .
H33 H 0.1395 0.3833 0.1728 0.046 Uiso 1 1 calc R . .
C34 C 0.7949(12) 0.6809(5) 0.5470(6) 0.033(3) Uani 1 1 d . . .
H34 H 0.8099 0.7065 0.5852 0.040 Uiso 1 1 calc R . .
C35 C 0.2409(12) 0.5123(6) 0.2052(6) 0.034(3) Uani 1 1 d . . .
H35 H 0.2229 0.5499 0.1905 0.041 Uiso 1 1 calc R . .
C36 C 0.8579(16) 0.4060(6) 0.3307(7) 0.047(4) Uani 1 1 d . . .
H36 H 0.8284 0.3708 0.3117 0.056 Uiso 1 1 calc R . .
C37 C 0.1641(12) 0.4678(6) 0.1717(8) 0.043(3) Uani 1 1 d . . .
H37 H 0.0961 0.4755 0.1346 0.051 Uiso 1 1 calc R . .
C38 C 0.7814(11) 0.6110(6) 0.0625(6) 0.030(3) Uani 1 1 d . . .
C39 C 0.6384(10) 0.5097(5) 0.1723(5) 0.023(2) Uani 1 1 d . . .
H39 H 0.7130 0.5110 0.2066 0.027 Uiso 1 1 calc R . .
C40 C 0.1963(15) 0.6197(7) 0.4684(8) 0.052(4) Uani 1 1 d . . .
H40 H 0.1505 0.6310 0.5031 0.063 Uiso 1 1 calc R . .
C41 C 0.2773(14) 0.5752(7) 0.4842(7) 0.046(4) Uani 1 1 d . . .
H41 H 0.2833 0.5562 0.5278 0.055 Uiso 1 1 calc R . .
F13 F 1.1408(6) 0.7668(3) 0.1233(3) 0.0276(14) Uani 1 1 d . . .
F14 F 1.2151(6) 0.6897(3) 0.1768(4) 0.0326(15) Uani 1 1 d . . .
F12 F 1.1810(6) 0.7635(3) 0.2386(4) 0.0352(16) Uani 1 1 d . . .
O2 O 0.4387(6) 0.6081(3) 0.2522(4) 0.0211(15) Uani 1 1 d . . .
C43 C 0.2555(11) 0.6298(5) 0.3539(7) 0.036(3) Uani 1 1 d . . .
H43 H 0.2489 0.6481 0.3098 0.043 Uiso 1 1 calc R . .
C48 C 1.1345(10) 0.7330(5) 0.1795(5) 0.023(2) Uani 1 1 d . . .
C44 C 0.2937(13) 0.4009(5) 0.2494(7) 0.038(3) Uani 1 1 d . . .
H44 H 0.3114 0.3633 0.2640 0.046 Uiso 1 1 calc R . .
C45 C 0.9413(14) 0.5111(6) 0.3866(9) 0.051(4) Uani 1 1 d . . .
H45 H 0.9703 0.5463 0.4063 0.061 Uiso 1 1 calc R . .
C46 C 0.1762(13) 0.6504(6) 0.4029(7) 0.042(3) Uani 1 1 d U . .
H46 H 0.1186 0.6804 0.3924 0.050 Uiso 1 1 calc R . .
C47 C 1.0269(16) 0.4670(8) 0.3822(11) 0.073(6) Uani 1 1 d . . .
H47 H 1.1133 0.4727 0.3992 0.087 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C42 C36 1.35(2) . ?
C42 C47 1.39(2) . ?
C42 H42 0.9300 . ?
Ir1 C8 2.014(10) . ?
Ir1 C4 2.017(9) . ?
Ir1 N1 2.019(8) . ?
Ir1 N3 2.023(8) . ?
Ir1 O2 2.159(7) . ?
Ir1 O1 2.162(6) . ?
P1 O1 1.523(6) . ?
P1 N5 1.594(9) . ?
P1 C17 1.801(11) . ?
P1 C7 1.807(10) . ?
P2 O2 1.518(8) . ?
P2 N5 1.585(9) . ?
P2 C19 1.806(11) . ?
P2 C24 1.814(10) . ?
N1 C26 1.351(13) . ?
N1 C15 1.356(12) . ?
F6 C22 1.342(12) . ?
N3 C39 1.341(13) . ?
N3 C16 1.363(12) . ?
F5 C22 1.339(13) . ?
F11 C14 1.333(12) . ?
F7 C38 1.358(14) . ?
F9 C38 1.342(15) . ?
F8 C38 1.350(12) . ?
F4 C22 1.362(12) . ?
N2 C15 1.333(12) . ?
N2 C23 1.348(14) . ?
C1 C7 1.379(14) . ?
C1 C11 1.390(14) . ?
C1 H1 0.9300 . ?
C2 C32 1.370(13) . ?
C2 C4 1.431(13) . ?
C2 C15 1.465(13) . ?
C3 C36 1.365(18) . ?
C3 C17 1.381(16) . ?
C3 H3 0.9300 . ?
C4 C12 1.410(13) . ?
F10 C31 1.341(14) . ?
C5 N4 1.321(17) . ?
C5 C31 1.368(17) . ?
C5 H5 0.9300 . ?
C6 C18 1.398(14) . ?
C6 C7 1.399(14) . ?
C6 H6 0.9300 . ?
C8 C20 1.419(15) . ?
C8 C9 1.426(15) . ?
C9 C13 1.395(13) . ?
C9 C16 1.457(15) . ?
C10 C21 1.380(15) . ?
C10 C12 1.400(14) . ?
C10 H10 0.9300 . ?
C11 C34 1.381(17) . ?
C11 H11 0.9300 . ?
F3 C28 1.312(14) . ?
C12 C38 1.508(14) . ?
C13 C29 1.345(17) . ?
C13 H13 0.9300 . ?
C14 C26 1.371(15) . ?
C14 C23 1.372(16) . ?
N4 C16 1.333(14) . ?
F2 C28 1.326(17) . ?
C17 C45 1.382(18) . ?
C18 C34 1.359(17) . ?
C18 H18 0.9300 . ?
C19 C43 1.369(17) . ?
C19 C25 1.414(15) . ?
C20 C30 1.390(14) . ?
C20 C22 1.490(16) . ?
C21 C32 1.383(14) . ?
C21 C48 1.491(14) . ?
C23 H23 0.9300 . ?
C24 C35 1.375(15) . ?
C24 C27 1.388(16) . ?
C25 C41 1.377(17) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C44 1.392(16) . ?
C27 H27 0.9300 . ?
C28 F1 1.334(15) . ?
C28 C29 1.494(15) . ?
C29 C30 1.382(17) . ?
C30 H30 0.9300 . ?
C31 C39 1.371(15) . ?
C32 H32 0.9300 . ?
C33 C37 1.363(19) . ?
C33 C44 1.397(18) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C37 1.402(17) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C39 H39 0.9300 . ?
C40 C41 1.35(2) . ?
C40 C46 1.41(2) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
F13 C48 1.340(12) . ?
F14 C48 1.335(12) . ?
F12 C48 1.344(12) . ?
C43 C46 1.454(17) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 C47 1.39(2) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 H47 0.9300 . ?

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
C36 C42 C47 119.0(14) . . ?
C36 C42 H42 120.5 . . ?
C47 C42 H42 120.5 . . ?
C8 Ir1 C4 99.6(4) . . ?
C8 Ir1 N1 104.7(4) . . ?
C4 Ir1 N1 81.8(4) . . ?
C8 Ir1 N3 81.4(4) . . ?
C4 Ir1 N3 103.3(4) . . ?
N1 Ir1 N3 171.5(3) . . ?
C8 Ir1 O2 87.8(3) . . ?
C4 Ir1 O2 168.9(3) . . ?
N1 Ir1 O2 88.3(3) . . ?
N3 Ir1 O2 85.9(3) . . ?
C8 Ir1 O1 172.1(4) . . ?
C4 Ir1 O1 83.1(3) . . ?
N1 Ir1 O1 83.1(3) . . ?
N3 Ir1 O1 90.7(3) . . ?
O2 Ir1 O1 90.8(2) . . ?
O1 P1 N5 118.2(4) . . ?
O1 P1 C17 105.6(5) . . ?
N5 P1 C17 106.7(5) . . ?
O1 P1 C7 105.5(4) . . ?
N5 P1 C7 111.8(5) . . ?
C17 P1 C7 108.5(5) . . ?
O2 P2 N5 118.5(4) . . ?
O2 P2 C19 107.2(5) . . ?
N5 P2 C19 110.2(5) . . ?
O2 P2 C24 108.8(4) . . ?
N5 P2 C24 107.2(5) . . ?
C19 P2 C24 104.1(5) . . ?
P1 O1 Ir1 128.4(4) . . ?
C26 N1 C15 117.9(9) . . ?
C26 N1 Ir1 126.8(7) . . ?
C15 N1 Ir1 114.2(6) . . ?
C39 N3 C16 117.9(9) . . ?
C39 N3 Ir1 126.5(7) . . ?
C16 N3 Ir1 114.3(7) . . ?
C15 N2 C23 117.2(9) . . ?
C7 C1 C11 120.8(10) . . ?
C7 C1 H1 119.6 . . ?
C11 C1 H1 119.6 . . ?
C32 C2 C4 123.8(9) . . ?
C32 C2 C15 120.7(9) . . ?
C4 C2 C15 115.5(8) . . ?
C36 C3 C17 121.6(13) . . ?
C36 C3 H3 119.2 . . ?
C17 C3 H3 119.2 . . ?
C12 C4 C2 114.5(8) . . ?
C12 C4 Ir1 134.3(7) . . ?
C2 C4 Ir1 110.8(7) . . ?
N4 C5 C31 121.7(11) . . ?
N4 C5 H5 119.1 . . ?
C31 C5 H5 119.1 . . ?
C18 C6 C7 119.0(10) . . ?
C18 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C1 C7 C6 119.5(9) . . ?
C1 C7 P1 120.4(8) . . ?
C6 C7 P1 120.0(8) . . ?
C20 C8 C9 114.2(9) . . ?
C20 C8 Ir1 134.7(8) . . ?
C9 C8 Ir1 111.0(7) . . ?
C13 C9 C8 122.3(10) . . ?
C13 C9 C16 121.3(10) . . ?
C8 C9 C16 116.3(9) . . ?
C21 C10 C12 121.3(9) . . ?
C21 C10 H10 119.4 . . ?
C12 C10 H10 119.4 . . ?
C34 C11 C1 119.2(11) . . ?
C34 C11 H11 120.4 . . ?
C1 C11 H11 120.4 . . ?
C10 C12 C4 121.3(9) . . ?
C10 C12 C38 115.6(9) . . ?
C4 C12 C38 123.1(9) . . ?
C29 C13 C9 121.0(11) . . ?
C29 C13 H13 119.5 . . ?
C9 C13 H13 119.5 . . ?
F11 C14 C26 120.2(10) . . ?
F11 C14 C23 119.9(10) . . ?
C26 C14 C23 119.9(10) . . ?
C5 N4 C16 117.6(10) . . ?
N2 C15 N1 124.6(9) . . ?
N2 C15 C2 120.9(9) . . ?
N1 C15 C2 114.5(8) . . ?
N4 C16 N3 123.8(10) . . ?
N4 C16 C9 122.7(9) . . ?
N3 C16 C9 113.5(9) . . ?
P2 N5 P1 127.1(6) . . ?
C3 C17 C45 118.4(11) . . ?
C3 C17 P1 120.6(9) . . ?
C45 C17 P1 120.6(9) . . ?
C34 C18 C6 120.7(11) . . ?
C34 C18 H18 119.7 . . ?
C6 C18 H18 119.7 . . ?
C43 C19 C25 118.2(11) . . ?
C43 C19 P2 122.7(9) . . ?
C25 C19 P2 119.1(9) . . ?
C30 C20 C8 122.1(11) . . ?
C30 C20 C22 116.6(10) . . ?
C8 C20 C22 121.2(9) . . ?
C10 C21 C32 119.2(9) . . ?
C10 C21 C48 118.2(9) . . ?
C32 C21 C48 122.6(9) . . ?
F5 C22 F6 105.8(9) . . ?
F5 C22 F4 105.1(9) . . ?
F6 C22 F4 104.5(8) . . ?
F5 C22 C20 114.1(9) . . ?
F6 C22 C20 113.9(9) . . ?
F4 C22 C20 112.5(9) . . ?
N2 C23 C14 120.8(10) . . ?
N2 C23 H23 119.6 . . ?
C14 C23 H23 119.6 . . ?
C35 C24 C27 119.9(10) . . ?
C35 C24 P2 119.8(9) . . ?
C27 C24 P2 120.2(8) . . ?
C41 C25 C19 120.1(13) . . ?
C41 C25 H25 119.9 . . ?
C19 C25 H25 119.9 . . ?
N1 C26 C14 119.5(10) . . ?
N1 C26 H26 120.2 . . ?
C14 C26 H26 120.2 . . ?
C24 C27 C44 119.6(11) . . ?
C24 C27 H27 120.2 . . ?
C44 C27 H27 120.2 . . ?
F3 C28 F2 106.1(11) . . ?
F3 C28 F1 105.9(12) . . ?
F2 C28 F1 104.7(12) . . ?
F3 C28 C29 113.7(11) . . ?
F2 C28 C29 113.8(11) . . ?
F1 C28 C29 111.9(10) . . ?
C13 C29 C30 119.5(10) . . ?
C13 C29 C28 121.1(12) . . ?
C30 C29 C28 119.4(11) . . ?
C29 C30 C20 120.7(11) . . ?
C29 C30 H30 119.6 . . ?
C20 C30 H30 119.6 . . ?
F10 C31 C5 121.2(11) . . ?
F10 C31 C39 119.6(10) . . ?
C5 C31 C39 119.2(11) . . ?
C2 C32 C21 119.6(9) . . ?
C2 C32 H32 120.2 . . ?
C21 C32 H32 120.2 . . ?
C37 C33 C44 121.0(11) . . ?
C37 C33 H33 119.5 . . ?
C44 C33 H33 119.5 . . ?
C18 C34 C11 120.7(10) . . ?
C18 C34 H34 119.6 . . ?
C11 C34 H34 119.6 . . ?
C24 C35 C37 120.9(12) . . ?
C24 C35 H35 119.5 . . ?
C37 C35 H35 119.5 . . ?
C42 C36 C3 120.8(14) . . ?
C42 C36 H36 119.6 . . ?
C3 C36 H36 119.6 . . ?
C33 C37 C35 119.0(11) . . ?
C33 C37 H37 120.5 . . ?
C35 C37 H37 120.5 . . ?
F9 C38 F8 105.7(9) . . ?
F9 C38 F7 108.6(10) . . ?
F8 C38 F7 105.0(9) . . ?
F9 C38 C12 113.5(9) . . ?
F8 C38 C12 112.2(9) . . ?
F7 C38 C12 111.2(9) . . ?
N3 C39 C31 119.7(10) . . ?
N3 C39 H39 120.1 . . ?
C31 C39 H39 120.1 . . ?
C41 C40 C46 124.7(12) . . ?
C41 C40 H40 117.6 . . ?
C46 C40 H40 117.6 . . ?
C40 C41 C25 120.3(13) . . ?
C40 C41 H41 119.9 . . ?
C25 C41 H41 119.9 . . ?
P2 O2 Ir1 128.5(4) . . ?
C19 C43 C46 124.0(12) . . ?
C19 C43 H43 118.0 . . ?
C46 C43 H43 118.0 . . ?
F14 C48 F13 106.7(8) . . ?
F14 C48 F12 107.1(9) . . ?
F13 C48 F12 106.5(9) . . ?
F14 C48 C21 111.9(9) . . ?
F13 C48 C21 112.1(8) . . ?
F12 C48 C21 112.3(8) . . ?
C27 C44 C33 119.7(12) . . ?
C27 C44 H44 120.2 . . ?
C33 C44 H44 120.2 . . ?
C17 C45 C47 119.4(14) . . ?
C17 C45 H45 120.3 . . ?
C47 C45 H45 120.3 . . ?
C40 C46 C43 112.6(13) . . ?
C40 C46 H46 123.7 . . ?
C43 C46 H46 123.7 . . ?
C42 C47 C45 120.6(16) . . ?
C42 C47 H47 119.7 . . ?
C45 C47 H47 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         5.302
_refine_diff_density_min         -4.676
_refine_diff_density_rms         0.249
####################################################################### 
# 
# 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_hhb_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1828771'
_audit_update_record             
;
2018-03-10 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H15 F14 Ir N4 O2'
_chemical_formula_sum            'C29 H15 F14 Ir N4 O2'
_chemical_formula_weight         909.90

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   19.7352(17)
_cell_length_b                   10.5902(10)
_cell_length_c                   16.4426(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.5540(10)
_cell_angle_gamma                90.00
_cell_volume                     3046.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5140
_cell_measurement_theta_max      27.024
_cell_measurement_theta_min      2.248

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1738.7
_exptl_absorpt_coefficient_mu    4.503
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.404
_exptl_absorpt_correction_T_max  0.445
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10124
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.58
_reflns_number_total             3519
_reflns_number_gt                3223
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0314P)²+3.4645P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3519
_refine_ls_number_parameters     231
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F7A F 0.3842(5) -0.0388(4) 0.4497(6) 0.180(4) Uani 0.991(17) 1 d PU A 1
Ir1 Ir 0.5000 0.441435(17) 0.2500 0.02786(7) Uani 1 2 d SU . .
O1 O 0.56656(17) 0.5822(3) 0.22989(19) 0.0437(7) Uani 1 1 d U . .
F1 F 0.71840(16) 0.6232(3) 0.56801(18) 0.0698(8) Uani 1 1 d U . .
N1 N 0.56671(17) 0.4549(3) 0.3887(2) 0.0328(6) Uani 1 1 d U . .
F2 F 0.38879(19) 0.1934(3) 0.1056(2) 0.0757(9) Uani 1 1 d U . .
F3 F 0.30391(17) 0.3210(4) 0.1017(2) 0.0840(10) Uani 1 1 d U . .
N2 N 0.5706(2) 0.4018(4) 0.5309(2) 0.0500(9) Uani 1 1 d U . .
C9 C 0.44532(19) 0.3109(3) 0.2909(2) 0.0324(7) Uani 1 1 d U . .
F4 F 0.2914(2) 0.1216(4) 0.1131(2) 0.1044(13) Uani 1 1 d U . .
C4 C 0.6268(2) 0.5321(4) 0.4315(3) 0.0407(9) Uani 1 1 d U . .
H4 H 0.6465 0.5764 0.3982 0.049 Uiso 1 1 calc R . .
C11 C 0.3833(2) 0.2267(4) 0.2445(3) 0.0408(8) Uani 1 1 d U . .
C13 C 0.3554(3) 0.1518(4) 0.2918(3) 0.0524(11) Uani 1 1 d U . .
H13 H 0.3144 0.0982 0.2590 0.063 Uiso 1 1 calc R . .
C7 C 0.5407(2) 0.3921(4) 0.4398(2) 0.0363(8) Uani 1 1 d U . .
C10 C 0.4478(2) 0.2336(4) 0.4344(3) 0.0481(10) Uani 1 1 d U . .
H10 H 0.4702 0.2361 0.4981 0.058 Uiso 1 1 calc R . .
C5 C 0.6588(2) 0.5448(4) 0.5246(3) 0.0482(10) Uani 1 1 d U . .
C8 C 0.4755(2) 0.3101(4) 0.3874(2) 0.0366(8) Uani 1 1 d U . .
C6 C 0.6298(3) 0.4795(5) 0.5730(3) 0.0523(11) Uani 1 1 d U . .
H6 H 0.6516 0.4894 0.6363 0.063 Uiso 1 1 calc R . .
C12 C 0.3873(3) 0.1549(4) 0.3863(3) 0.0535(11) Uani 1 1 d U A .
F5 F 0.3669(4) 0.1145(5) 0.5134(4) 0.148(3) Uani 0.936(15) 1 d PU A 1
C3 C 0.5569(3) 0.7000(4) 0.2354(3) 0.0549(11) Uani 1 1 d U . .
F6 F 0.2854(4) 0.0595(7) 0.3940(6) 0.211(4) Uani 1 1 d U A 1
C14 C 0.3425(3) 0.2157(5) 0.1421(3) 0.0581(12) Uani 1 1 d U . .
C15 C 0.3576(4) 0.0708(6) 0.4361(5) 0.0781(18) Uani 1 1 d U . .
C1 C 0.6154(4) 0.7825(6) 0.2254(4) 0.0887(19) Uani 1 1 d U . .
H1A H 0.6659 0.7532 0.2662 0.133 Uiso 1 1 calc R . .
H1B H 0.6097 0.8682 0.2403 0.133 Uiso 1 1 calc R . .
H1C H 0.6076 0.7785 0.1633 0.133 Uiso 1 1 calc R . .
C2 C 0.5000 0.7564(6) 0.2500 0.071(2) Uani 1 2 d SU . .
H2 H 0.5000 0.8443 0.2500 0.085 Uiso 1 2 calc SR . .


_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
F7A C15 1.251(7) . ?
Ir1 N1 2.043(3) . ?
Ir1 N1 2.043(3) 2_655 ?
Ir1 C9 2.049(3) 2_655 ?
Ir1 C9 2.049(3) . ?
Ir1 O1 2.112(3) . ?
Ir1 O1 2.112(3) 2_655 ?
O1 C3 1.272(5) . ?
F1 C5 1.343(5) . ?
N1 C4 1.341(5) . ?
N1 C7 1.347(5) . ?
F2 C14 1.328(6) . ?
F3 C14 1.340(6) . ?
N2 C6 1.331(6) . ?
N2 C7 1.336(5) . ?
C9 C8 1.414(5) . ?
C9 C11 1.418(5) . ?
F4 C14 1.339(5) . ?
C4 C5 1.367(6) . ?
C4 H4 0.9300 . ?
C11 C13 1.389(5) . ?
C11 C14 1.497(6) . ?
C13 C12 1.381(7) . ?
C13 H13 0.9300 . ?
C7 C8 1.458(5) . ?
C10 C12 1.368(7) . ?
C10 C8 1.395(5) . ?
C10 H10 0.9300 . ?
C5 C6 1.365(7) . ?
C6 H6 0.9300 . ?
C12 C15 1.502(6) . ?
F5 C15 1.283(8) . ?
C3 C2 1.389(6) . ?
C3 C1 1.515(7) . ?
F6 C15 1.269(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.389(6) 2_655 ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 N1 171.97(16) . 2_655 ?
N1 Ir1 C9 104.35(13) . 2_655 ?
N1 Ir1 C9 81.18(13) 2_655 2_655 ?
N1 Ir1 C9 81.18(13) . . ?
N1 Ir1 C9 104.35(13) 2_655 . ?
C9 Ir1 C9 95.13(19) 2_655 . ?
N1 Ir1 O1 89.94(11) . . ?
N1 Ir1 O1 84.39(11) 2_655 . ?
C9 Ir1 O1 87.99(13) 2_655 . ?
C9 Ir1 O1 171.06(12) . . ?
N1 Ir1 O1 84.39(11) . 2_655 ?
N1 Ir1 O1 89.94(11) 2_655 2_655 ?
C9 Ir1 O1 171.06(12) 2_655 2_655 ?
C9 Ir1 O1 87.99(13) . 2_655 ?
O1 Ir1 O1 90.18(17) . 2_655 ?
C3 O1 Ir1 123.9(3) . . ?
C4 N1 C7 118.3(3) . . ?
C4 N1 Ir1 125.8(3) . . ?
C7 N1 Ir1 115.3(2) . . ?
C6 N2 C7 117.2(4) . . ?
C8 C9 C11 114.2(3) . . ?
C8 C9 Ir1 111.1(3) . . ?
C11 C9 Ir1 134.7(3) . . ?
N1 C4 C5 119.1(4) . . ?
N1 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C13 C11 C9 121.7(4) . . ?
C13 C11 C14 116.0(4) . . ?
C9 C11 C14 122.3(3) . . ?
C12 C13 C11 121.6(4) . . ?
C12 C13 H13 119.2 . . ?
C11 C13 H13 119.2 . . ?
N2 C7 N1 124.3(4) . . ?
N2 C7 C8 121.4(3) . . ?
N1 C7 C8 114.3(3) . . ?
C12 C10 C8 119.6(4) . . ?
C12 C10 H10 120.2 . . ?
C8 C10 H10 120.2 . . ?
F1 C5 C6 120.2(4) . . ?
F1 C5 C4 119.6(4) . . ?
C6 C5 C4 120.2(4) . . ?
C10 C8 C9 123.8(4) . . ?
C10 C8 C7 118.9(3) . . ?
C9 C8 C7 117.3(3) . . ?
N2 C6 C5 120.9(4) . . ?
N2 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C10 C12 C13 119.1(4) . . ?
C10 C12 C15 120.2(5) . . ?
C13 C12 C15 120.7(5) . . ?
O1 C3 C2 126.4(5) . . ?
O1 C3 C1 114.4(5) . . ?
C2 C3 C1 119.2(5) . . ?
F2 C14 F4 105.6(4) . . ?
F2 C14 F3 105.9(4) . . ?
F4 C14 F3 106.4(4) . . ?
F2 C14 C11 113.5(4) . . ?
F4 C14 C11 112.5(4) . . ?
F3 C14 C11 112.3(4) . . ?
F7A C15 F6 106.5(7) . . ?
F7A C15 F5 107.6(7) . . ?
F6 C15 F5 100.7(6) . . ?
F7A C15 C12 114.1(5) . . ?
F6 C15 C12 112.4(6) . . ?
F5 C15 C12 114.4(5) . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C3 129.0(6) 2_655 . ?
C3 C2 H2 115.5 2_655 . ?
C3 C2 H2 115.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.954
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.101
####################################################################### 
# 
# 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_hhb_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1828766'
_audit_update_record             
;
2018-03-10 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H30 F12 Ir N5 O2 P2'
_chemical_formula_sum            'C48 H30 F12 Ir N5 O2 P2'
_chemical_formula_weight         1190.93

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

_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.713(3)
_cell_length_b                   11.791(3)
_cell_length_c                   18.760(5)
_cell_angle_alpha                80.084(5)
_cell_angle_beta                 84.606(5)
_cell_angle_gamma                87.756(5)
_cell_volume                     2323.3(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3164
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      23.69

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    3.036
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12809
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.1027
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8051
_reflns_number_gt                6257
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1553P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8051
_refine_ls_number_parameters     631
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.2221
_refine_ls_wR_factor_gt          0.1996
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.089
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.427403(16) 0.213772(15) 0.228599(9) 0.02674(5) Uani 1 1 d . . .
P3 P 0.62647(11) 0.35902(11) 0.30461(7) 0.0324(3) Uani 1 1 d . . .
P4 P 0.36859(12) 0.37836(11) 0.35710(7) 0.0320(3) Uani 1 1 d . . .
F13 F -0.1497(4) -0.0470(4) 0.2829(3) 0.1284(17) Uani 1 1 d . . .
F14 F -0.1997(3) 0.0873(4) 0.2047(3) 0.0820(15) Uani 1 1 d . . .
F15 F -0.1122(4) -0.0595(4) 0.1728(3) 0.1119(16) Uani 1 1 d . . .
F16 F 0.1343(3) 0.2687(4) 0.0337(2) 0.0893(14) Uani 1 1 d . . .
F17 F 0.3276(3) 0.2483(4) 0.05464(19) 0.0851(15) Uani 1 1 d . . .
F18 F 0.2141(4) 0.3793(3) 0.0931(3) 0.1004(16) Uani 1 1 d . . .
F19 F 0.5284(4) -0.1455(3) 0.1285(2) 0.0787(14) Uani 1 1 d . . .
F20 F 0.3870(3) -0.0530(3) 0.1835(2) 0.0715(13) Uani 1 1 d . . .
F21 F 0.5678(4) -0.0936(3) 0.2290(2) 0.0743(14) Uani 1 1 d . . .
F22 F 0.9233(4) 0.1444(7) -0.0198(3) 0.156(3) Uani 1 1 d . . .
F23 F 0.8210(6) 0.0239(5) -0.0524(3) 0.172(2) Uani 1 1 d . . .
F24 F 0.7972(5) 0.1913(6) -0.0954(3) 0.152(3) Uani 1 1 d . . .
O3 O 0.3264(3) 0.2872(3) 0.31620(18) 0.0369(10) Uani 1 1 d . . .
O4 O 0.6021(3) 0.2528(3) 0.27109(16) 0.0326(9) Uani 1 1 d . . .
N6 N 0.4183(4) 0.0694(3) 0.3076(2) 0.0347(11) Uani 1 1 d . . .
N7 N 0.2586(4) -0.0420(4) 0.3832(3) 0.0543(16) Uani 1 1 d . . .
N8 N 0.5913(4) 0.4666(4) 0.0686(2) 0.0429(13) Uani 1 1 d . . .
N9 N 0.4431(4) 0.3689(4) 0.1606(2) 0.0353(12) Uani 1 1 d . . .
N10 N 0.5085(4) 0.4253(3) 0.3377(2) 0.0341(11) Uani 1 1 d . . .
C13 C 0.5460(5) 0.3701(4) 0.1080(2) 0.0333(13) Uani 1 1 d . . .
C15 C 0.5628(5) 0.0513(4) 0.1249(3) 0.0363(14) Uani 1 1 d . . .
C16 C 0.2588(5) 0.4993(5) 0.3431(3) 0.0425(16) Uani 1 1 d . . .
C18 C 0.7173(5) 0.4610(5) 0.2402(3) 0.0420(15) Uani 1 1 d . . .
C21 C 0.3008(7) 0.6143(5) 0.3198(3) 0.057(2) Uani 1 1 d . . .
H21 H 0.3861 0.6292 0.3145 0.069 Uiso 1 1 calc R . .
C25 C 0.2960(4) 0.0331(4) 0.3226(3) 0.0327(13) Uani 1 1 d . . .
C29 C 0.6786(5) 0.2474(5) 0.0403(3) 0.0395(15) Uani 1 1 d . . .
H29 H 0.7149 0.3127 0.0123 0.047 Uiso 1 1 calc R . .
C30 C 0.3446(5) 0.3215(4) 0.4532(2) 0.0326(13) Uani 1 1 d . . .
C32 C 0.5893(4) 0.2563(5) 0.0979(3) 0.0377(15) Uani 1 1 d U . .
C36 C 0.2076(5) 0.0771(4) 0.2687(2) 0.0328(13) Uani 1 1 d . . .
C37 C 0.2575(6) 0.2363(5) 0.4799(3) 0.0553(19) Uani 1 1 d . . .
H37 H 0.2157 0.2038 0.4474 0.066 Uiso 1 1 calc R . .
C38 C 0.5044(5) 0.0313(4) 0.3537(3) 0.0411(15) Uani 1 1 d . . .
H38 H 0.5859 0.0578 0.3439 0.049 Uiso 1 1 calc R . .
C39 C 0.3856(7) 0.3253(5) 0.5766(3) 0.065(2) Uani 1 1 d . . .
H39 H 0.4338 0.3511 0.6090 0.077 Uiso 1 1 calc R . .
C40 C 0.6981(5) 0.5802(5) 0.2339(3) 0.0457(16) Uani 1 1 d . . .
H40 H 0.6320 0.6088 0.2619 0.055 Uiso 1 1 calc R . .
C41 C 0.8922(7) 0.4960(7) 0.1487(4) 0.083(3) Uani 1 1 d . . .
H41 H 0.9558 0.4683 0.1185 0.100 Uiso 1 1 calc R . .
C44 C 0.2888(6) 0.2491(6) 0.6019(3) 0.066(2) Uani 1 1 d . . .
H44 H 0.2632 0.2323 0.6513 0.079 Uiso 1 1 calc R . .
C46 C 0.5107(5) -0.0595(5) 0.1657(3) 0.0469(16) Uani 1 1 d . . .
C47 C 0.7123(5) 0.1375(5) 0.0256(3) 0.0445(16) Uani 1 1 d . . .
C48 C 0.5313(6) 0.5672(5) 0.0811(3) 0.058(2) Uani 1 1 d . . .
H48 H 0.5608 0.6361 0.0542 0.069 Uiso 1 1 calc R . .
C49 C 0.4731(5) -0.0465(5) 0.4151(3) 0.0476(16) Uani 1 1 d . . .
H49 H 0.5331 -0.0766 0.4464 0.057 Uiso 1 1 calc R . .
C50 C 0.2320(6) 0.1994(7) 0.5529(4) 0.073(2) Uani 1 1 d . . .
H50 H 0.1759 0.1404 0.5694 0.088 Uiso 1 1 calc R . .
C51 C 0.4323(6) 0.5714(5) 0.1300(3) 0.0465(17) Uani 1 1 d . . .
H51 H 0.3931 0.6412 0.1362 0.056 Uiso 1 1 calc R . .
C54 C 0.1372(6) 0.4772(6) 0.3488(4) 0.068(2) Uani 1 1 d . . .
H54 H 0.1112 0.4017 0.3632 0.082 Uiso 1 1 calc R . .
C56 C 0.4085(7) 0.3611(5) 0.5050(3) 0.065(2) Uani 1 1 d . . .
H56 H 0.4704 0.4152 0.4890 0.078 Uiso 1 1 calc R . .
C57 C 0.3488(6) -0.0791(5) 0.4293(3) 0.064(2) Uani 1 1 d . . .
H57 H 0.3258 -0.1286 0.4724 0.076 Uiso 1 1 calc R . .
C59 C 0.8169(6) 0.4180(7) 0.1972(4) 0.073(2) Uani 1 1 d . . .
H59 H 0.8323 0.3391 0.2009 0.087 Uiso 1 1 calc R . .
C61 C 0.2166(7) 0.7014(5) 0.3054(5) 0.076(3) Uani 1 1 d . . .
H61 H 0.2441 0.7765 0.2919 0.091 Uiso 1 1 calc R . .
C62 C 0.7739(6) 0.6553(6) 0.1877(4) 0.066(2) Uani 1 1 d . . .
H62 H 0.7594 0.7342 0.1846 0.080 Uiso 1 1 calc R . .
C63 C 0.5335(4) 0.1615(4) 0.1460(3) 0.0357(14) Uani 1 1 d U . .
C133 C 0.6546(6) 0.0401(5) 0.0662(3) 0.0520(18) Uani 1 1 d . . .
H133 H 0.6760 -0.0323 0.0549 0.062 Uiso 1 1 calc R . .
C165 C 0.0959(5) 0.0307(4) 0.2745(3) 0.0412(15) Uani 1 1 d . . .
H165 H 0.0694 -0.0202 0.3162 0.049 Uiso 1 1 calc R . .
C167 C 0.8739(6) 0.6137(6) 0.1447(4) 0.084(2) Uani 1 1 d . . .
H167 H 0.9272 0.6646 0.1140 0.101 Uiso 1 1 calc R . .
C168 C 0.0171(4) 0.0582(4) 0.2177(3) 0.0351(14) Uani 1 1 d . . .
C170 C 0.2569(5) 0.1601(5) 0.2110(3) 0.0415(16) Uani 1 1 d . . .
C205 C 0.8309(7) 0.3441(7) 0.4782(4) 0.079(2) Uani 1 1 d . . .
H205 H 0.8392 0.3900 0.5131 0.094 Uiso 1 1 calc R . .
C206 C 0.9067(6) 0.2411(7) 0.4766(4) 0.068(2) Uani 1 1 d U . .
H206 H 0.9603 0.2164 0.5126 0.082 Uiso 1 1 calc R . .
C207 C 0.2143(6) 0.2686(5) 0.0830(3) 0.0517(18) Uani 1 1 d . . .
C210 C 0.1807(5) 0.1854(4) 0.1533(3) 0.0380(15) Uani 1 1 d . . .
C215 C 0.8994(7) 0.1795(8) 0.4212(4) 0.090(3) Uani 1 1 d U . .
H215 H 0.9533 0.1169 0.4168 0.108 Uiso 1 1 calc R . .
C216 C 0.8116(5) 0.2117(6) 0.3727(4) 0.061(2) Uani 1 1 d . . .
H216 H 0.8040 0.1663 0.3375 0.073 Uiso 1 1 calc R . .
C217 C 0.7472(7) 0.3729(6) 0.4279(3) 0.064(2) Uani 1 1 d . . .
H217 H 0.6973 0.4387 0.4303 0.077 Uiso 1 1 calc R . .
C219 C 0.7307(5) 0.3111(5) 0.3730(3) 0.0417(16) Uani 1 1 d . . .
C221 C 0.3899(5) 0.4685(4) 0.1711(2) 0.0383(15) Uani 1 1 d . . .
H221 H 0.3232 0.4697 0.2065 0.046 Uiso 1 1 calc R . .
C222 C 0.0603(5) 0.1412(4) 0.1576(3) 0.0354(14) Uani 1 1 d . . .
H222 H 0.0084 0.1666 0.1207 0.043 Uiso 1 1 calc R . .
C225 C -0.1100(5) 0.0084(5) 0.2194(3) 0.0449(16) Uani 1 1 d . . .
C226 C 0.8118(7) 0.1232(6) -0.0352(3) 0.066(2) Uani 1 1 d . . .
C151 C 0.0851(6) 0.6795(6) 0.3108(5) 0.081(3) Uani 1 1 d . . .
H151 H 0.0271 0.7391 0.2996 0.098 Uiso 1 1 calc R . .
C150 C 0.0466(6) 0.5665(6) 0.3331(4) 0.073(2) Uani 1 1 d U . .
H150 H -0.0382 0.5498 0.3378 0.088 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C63 2.004(5) . ?
Ir1 C170 2.030(6) . ?
Ir1 N9 2.045(4) . ?
Ir1 N6 2.054(4) . ?
Ir1 O3 2.169(3) . ?
Ir1 O4 2.196(3) . ?
P3 O4 1.536(4) . ?
P3 N10 1.592(4) . ?
P3 C219 1.784(6) . ?
P3 C18 1.796(5) . ?
P4 O3 1.528(4) . ?
P4 N10 1.606(4) . ?
P4 C30 1.811(5) . ?
P4 C16 1.812(6) . ?
F13 C225 1.297(7) . ?
F14 C225 1.325(6) . ?
F15 C225 1.284(8) . ?
F16 C207 1.318(7) . ?
F17 C207 1.310(7) . ?
F18 C207 1.350(8) . ?
F19 C46 1.325(7) . ?
F20 C46 1.339(6) . ?
F21 C46 1.378(7) . ?
F22 C226 1.298(9) . ?
F23 C226 1.265(9) . ?
F24 C226 1.287(8) . ?
N6 C38 1.336(7) . ?
N6 C25 1.383(6) . ?
N7 C25 1.354(6) . ?
N7 C57 1.367(8) . ?
N8 C13 1.328(6) . ?
N8 C48 1.371(8) . ?
N9 C221 1.323(7) . ?
N9 C13 1.407(6) . ?
C13 C32 1.440(7) . ?
C15 C133 1.427(7) . ?
C15 C63 1.437(7) . ?
C15 C46 1.495(7) . ?
C16 C54 1.329(9) . ?
C16 C21 1.429(8) . ?
C18 C40 1.398(8) . ?
C18 C59 1.409(9) . ?
C21 C61 1.348(9) . ?
C21 H21 0.9300 . ?
C25 C36 1.465(7) . ?
C29 C32 1.389(7) . ?
C29 C47 1.397(8) . ?
C29 H29 0.9300 . ?
C30 C56 1.392(9) . ?
C30 C37 1.393(8) . ?
C32 C63 1.423(7) . ?
C36 C165 1.322(7) . ?
C36 C170 1.406(7) . ?
C37 C50 1.369(9) . ?
C37 H37 0.9300 . ?
C38 C49 1.368(7) . ?
C38 H38 0.9300 . ?
C39 C56 1.339(8) . ?
C39 C44 1.393(10) . ?
C39 H39 0.9300 . ?
C40 C62 1.361(8) . ?
C40 H40 0.9300 . ?
C41 C167 1.384(11) . ?
C41 C59 1.399(10) . ?
C41 H41 0.9300 . ?
C44 C50 1.370(11) . ?
C44 H44 0.9300 . ?
C47 C133 1.396(8) . ?
C47 C226 1.512(8) . ?
C48 C51 1.340(8) . ?
C48 H48 0.9300 . ?
C49 C57 1.390(9) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 C221 1.388(7) . ?
C51 H51 0.9300 . ?
C54 C150 1.416(10) . ?
C54 H54 0.9300 . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C59 H59 0.9300 . ?
C61 C151 1.432(10) . ?
C61 H61 0.9300 . ?
C62 C167 1.404(10) . ?
C62 H62 0.9300 . ?
C133 H133 0.9300 . ?
C165 C168 1.408(7) . ?
C165 H165 0.9300 . ?
C167 H167 0.9300 . ?
C168 C222 1.416(6) . ?
C168 C225 1.500(7) . ?
C170 C210 1.402(8) . ?
C205 C217 1.355(10) . ?
C205 C206 1.437(11) . ?
C205 H205 0.9300 . ?
C206 C215 1.376(12) . ?
C206 H206 0.9300 . ?
C207 C210 1.524(7) . ?
C210 C222 1.401(7) . ?
C215 C216 1.367(10) . ?
C215 H215 0.9300 . ?
C216 C219 1.430(8) . ?
C216 H216 0.9300 . ?
C217 C219 1.388(9) . ?
C217 H217 0.9300 . ?
C221 H221 0.9300 . ?
C222 H222 0.9300 . ?
C151 C150 1.393(10) . ?
C151 H151 0.9300 . ?
C150 H150 0.9300 . ?

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
C63 Ir1 C170 100.2(2) . . ?
C63 Ir1 N9 81.49(18) . . ?
C170 Ir1 N9 102.94(18) . . ?
C63 Ir1 N6 103.53(18) . . ?
C170 Ir1 N6 82.07(18) . . ?
N9 Ir1 N6 172.31(17) . . ?
C63 Ir1 O3 173.42(17) . . ?
C170 Ir1 O3 85.15(18) . . ?
N9 Ir1 O3 93.67(15) . . ?
N6 Ir1 O3 80.84(15) . . ?
C63 Ir1 O4 87.55(16) . . ?
C170 Ir1 O4 167.90(16) . . ?
N9 Ir1 O4 87.28(14) . . ?
N6 Ir1 O4 87.13(14) . . ?
O3 Ir1 O4 87.76(12) . . ?
O4 P3 N10 117.9(2) . . ?
O4 P3 C219 105.9(2) . . ?
N10 P3 C219 110.0(2) . . ?
O4 P3 C18 110.3(2) . . ?
N10 P3 C18 108.4(2) . . ?
C219 P3 C18 103.3(2) . . ?
O3 P4 N10 118.3(2) . . ?
O3 P4 C30 107.4(2) . . ?
N10 P4 C30 109.8(2) . . ?
O3 P4 C16 107.2(2) . . ?
N10 P4 C16 108.7(2) . . ?
C30 P4 C16 104.7(2) . . ?
P4 O3 Ir1 128.96(19) . . ?
P3 O4 Ir1 126.69(19) . . ?
C38 N6 C25 120.4(4) . . ?
C38 N6 Ir1 126.9(3) . . ?
C25 N6 Ir1 110.3(3) . . ?
C25 N7 C57 116.0(5) . . ?
C13 N8 C48 116.4(4) . . ?
C221 N9 C13 118.3(4) . . ?
C221 N9 Ir1 127.4(3) . . ?
C13 N9 Ir1 112.2(3) . . ?
P3 N10 P4 126.7(3) . . ?
N8 C13 N9 122.8(4) . . ?
N8 C13 C32 124.2(4) . . ?
N9 C13 C32 112.9(4) . . ?
C133 C15 C63 120.8(5) . . ?
C133 C15 C46 115.2(5) . . ?
C63 C15 C46 123.8(5) . . ?
C54 C16 C21 120.2(6) . . ?
C54 C16 P4 118.0(5) . . ?
C21 C16 P4 121.5(4) . . ?
C40 C18 C59 119.0(5) . . ?
C40 C18 P3 123.2(4) . . ?
C59 C18 P3 117.7(5) . . ?
C61 C21 C16 119.9(6) . . ?
C61 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
N7 C25 N6 122.2(4) . . ?
N7 C25 C36 120.7(4) . . ?
N6 C25 C36 117.1(4) . . ?
C32 C29 C47 118.1(5) . . ?
C32 C29 H29 120.9 . . ?
C47 C29 H29 120.9 . . ?
C56 C30 C37 115.9(5) . . ?
C56 C30 P4 122.8(4) . . ?
C37 C30 P4 121.3(4) . . ?
C29 C32 C63 125.1(5) . . ?
C29 C32 C13 117.6(4) . . ?
C63 C32 C13 117.3(4) . . ?
C165 C36 C170 126.1(5) . . ?
C165 C36 C25 119.1(4) . . ?
C170 C36 C25 114.5(4) . . ?
C50 C37 C30 121.5(6) . . ?
C50 C37 H37 119.2 . . ?
C30 C37 H37 119.2 . . ?
N6 C38 C49 120.2(5) . . ?
N6 C38 H38 119.9 . . ?
C49 C38 H38 119.9 . . ?
C56 C39 C44 119.4(7) . . ?
C56 C39 H39 120.3 . . ?
C44 C39 H39 120.3 . . ?
C62 C40 C18 121.6(5) . . ?
C62 C40 H40 119.2 . . ?
C18 C40 H40 119.2 . . ?
C167 C41 C59 121.2(7) . . ?
C167 C41 H41 119.4 . . ?
C59 C41 H41 119.4 . . ?
C50 C44 C39 118.8(6) . . ?
C50 C44 H44 120.6 . . ?
C39 C44 H44 120.6 . . ?
F19 C46 F20 105.8(5) . . ?
F19 C46 F21 106.2(4) . . ?
F20 C46 F21 107.6(5) . . ?
F19 C46 C15 112.9(5) . . ?
F20 C46 C15 113.0(4) . . ?
F21 C46 C15 110.8(5) . . ?
C133 C47 C29 120.7(5) . . ?
C133 C47 C226 119.3(5) . . ?
C29 C47 C226 120.0(5) . . ?
C51 C48 N8 123.5(5) . . ?
C51 C48 H48 118.2 . . ?
N8 C48 H48 118.2 . . ?
C38 C49 C57 117.9(5) . . ?
C38 C49 H49 121.1 . . ?
C57 C49 H49 121.1 . . ?
C37 C50 C44 120.3(6) . . ?
C37 C50 H50 119.9 . . ?
C44 C50 H50 119.9 . . ?
C48 C51 C221 118.2(5) . . ?
C48 C51 H51 120.9 . . ?
C221 C51 H51 120.9 . . ?
C16 C54 C150 121.2(6) . . ?
C16 C54 H54 119.4 . . ?
C150 C54 H54 119.4 . . ?
C39 C56 C30 123.3(6) . . ?
C39 C56 H56 118.3 . . ?
C30 C56 H56 118.3 . . ?
N7 C57 C49 123.3(5) . . ?
N7 C57 H57 118.4 . . ?
C49 C57 H57 118.4 . . ?
C41 C59 C18 118.8(7) . . ?
C41 C59 H59 120.6 . . ?
C18 C59 H59 120.6 . . ?
C21 C61 C151 120.8(6) . . ?
C21 C61 H61 119.6 . . ?
C151 C61 H61 119.6 . . ?
C40 C62 C167 120.1(6) . . ?
C40 C62 H62 120.0 . . ?
C167 C62 H62 120.0 . . ?
C32 C63 C15 114.5(4) . . ?
C32 C63 Ir1 111.4(4) . . ?
C15 C63 Ir1 134.1(3) . . ?
C47 C133 C15 120.3(5) . . ?
C47 C133 H133 119.9 . . ?
C15 C133 H133 119.9 . . ?
C36 C165 C168 120.3(4) . . ?
C36 C165 H165 119.9 . . ?
C168 C165 H165 119.9 . . ?
C41 C167 C62 119.2(6) . . ?
C41 C167 H167 120.4 . . ?
C62 C167 H167 120.4 . . ?
C165 C168 C222 116.9(4) . . ?
C165 C168 C225 123.8(4) . . ?
C222 C168 C225 119.3(4) . . ?
C210 C170 C36 113.9(5) . . ?
C210 C170 Ir1 133.8(4) . . ?
C36 C170 Ir1 112.2(4) . . ?
C217 C205 C206 118.6(7) . . ?
C217 C205 H205 120.7 . . ?
C206 C205 H205 120.7 . . ?
C215 C206 C205 119.5(7) . . ?
C215 C206 H206 120.3 . . ?
C205 C206 H206 120.3 . . ?
F17 C207 F16 109.1(5) . . ?
F17 C207 F18 105.1(5) . . ?
F16 C207 F18 104.3(5) . . ?
F17 C207 C210 111.8(5) . . ?
F16 C207 C210 113.4(5) . . ?
F18 C207 C210 112.6(5) . . ?
C222 C210 C170 121.9(4) . . ?
C222 C210 C207 113.3(5) . . ?
C170 C210 C207 124.6(5) . . ?
C216 C215 C206 119.0(8) . . ?
C216 C215 H215 120.5 . . ?
C206 C215 H215 120.5 . . ?
C215 C216 C219 123.8(7) . . ?
C215 C216 H216 118.1 . . ?
C219 C216 H216 118.1 . . ?
C205 C217 C219 124.5(7) . . ?
C205 C217 H217 117.7 . . ?
C219 C217 H217 117.7 . . ?
C217 C219 C216 114.3(5) . . ?
C217 C219 P3 122.3(5) . . ?
C216 C219 P3 123.2(5) . . ?
N9 C221 C51 120.8(5) . . ?
N9 C221 H221 119.6 . . ?
C51 C221 H221 119.6 . . ?
C210 C222 C168 120.4(4) . . ?
C210 C222 H222 119.8 . . ?
C168 C222 H222 119.8 . . ?
F15 C225 F13 108.5(5) . . ?
F15 C225 F14 106.2(5) . . ?
F13 C225 F14 103.2(4) . . ?
F15 C225 C168 111.7(5) . . ?
F13 C225 C168 113.2(5) . . ?
F14 C225 C168 113.5(5) . . ?
F23 C226 F24 104.3(6) . . ?
F23 C226 F22 105.1(7) . . ?
F24 C226 F22 104.4(6) . . ?
F23 C226 C47 115.3(6) . . ?
F24 C226 C47 114.3(6) . . ?
F22 C226 C47 112.3(6) . . ?
C150 C151 C61 118.2(6) . . ?
C150 C151 H151 120.9 . . ?
C61 C151 H151 120.9 . . ?
C151 C150 C54 119.7(6) . . ?
C151 C150 H150 120.2 . . ?
C54 C150 H150 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N10 P4 O3 Ir1 -3.3(3) . . . . ?
C30 P4 O3 Ir1 -128.1(3) . . . . ?
C16 P4 O3 Ir1 119.8(3) . . . . ?
C63 Ir1 O3 P4 -18.1(15) . . . . ?
C170 Ir1 O3 P4 -163.3(3) . . . . ?
N9 Ir1 O3 P4 -60.6(3) . . . . ?
N6 Ir1 O3 P4 114.0(3) . . . . ?
O4 Ir1 O3 P4 26.5(2) . . . . ?
N10 P3 O4 Ir1 23.0(3) . . . . ?
C219 P3 O4 Ir1 146.6(2) . . . . ?
C18 P3 O4 Ir1 -102.2(3) . . . . ?
C63 Ir1 O4 P3 138.6(2) . . . . ?
C170 Ir1 O4 P3 -90.9(9) . . . . ?
N9 Ir1 O4 P3 57.0(2) . . . . ?
N6 Ir1 O4 P3 -117.7(2) . . . . ?
O3 Ir1 O4 P3 -36.8(2) . . . . ?
C63 Ir1 N6 C38 81.6(5) . . . . ?
C170 Ir1 N6 C38 -179.7(5) . . . . ?
N9 Ir1 N6 C38 -48.6(14) . . . . ?
O3 Ir1 N6 C38 -93.4(4) . . . . ?
O4 Ir1 N6 C38 -5.2(4) . . . . ?
C63 Ir1 N6 C25 -116.3(4) . . . . ?
C170 Ir1 N6 C25 -17.6(4) . . . . ?
N9 Ir1 N6 C25 113.5(11) . . . . ?
O3 Ir1 N6 C25 68.8(3) . . . . ?
O4 Ir1 N6 C25 156.9(3) . . . . ?
C63 Ir1 N9 C221 176.9(5) . . . . ?
C170 Ir1 N9 C221 78.3(5) . . . . ?
N6 Ir1 N9 C221 -51.7(14) . . . . ?
O3 Ir1 N9 C221 -7.6(5) . . . . ?
O4 Ir1 N9 C221 -95.1(5) . . . . ?
C63 Ir1 N9 C13 -20.2(3) . . . . ?
C170 Ir1 N9 C13 -118.9(4) . . . . ?
N6 Ir1 N9 C13 111.1(11) . . . . ?
O3 Ir1 N9 C13 155.3(3) . . . . ?
O4 Ir1 N9 C13 67.7(3) . . . . ?
O4 P3 N10 P4 15.4(4) . . . . ?
C219 P3 N10 P4 -106.1(3) . . . . ?
C18 P3 N10 P4 141.6(3) . . . . ?
O3 P4 N10 P3 -25.6(4) . . . . ?
C30 P4 N10 P3 98.0(3) . . . . ?
C16 P4 N10 P3 -148.0(3) . . . . ?
C48 N8 C13 N9 -0.7(8) . . . . ?
C48 N8 C13 C32 174.0(5) . . . . ?
C221 N9 C13 N8 -0.3(7) . . . . ?
Ir1 N9 C13 N8 -164.9(4) . . . . ?
C221 N9 C13 C32 -175.6(5) . . . . ?
Ir1 N9 C13 C32 19.8(5) . . . . ?
O3 P4 C16 C54 44.0(5) . . . . ?
N10 P4 C16 C54 173.0(5) . . . . ?
C30 P4 C16 C54 -69.8(5) . . . . ?
O3 P4 C16 C21 -130.0(5) . . . . ?
N10 P4 C16 C21 -1.1(5) . . . . ?
C30 P4 C16 C21 116.1(5) . . . . ?
O4 P3 C18 C40 142.6(5) . . . . ?
N10 P3 C18 C40 12.1(6) . . . . ?
C219 P3 C18 C40 -104.6(5) . . . . ?
O4 P3 C18 C59 -41.1(5) . . . . ?
N10 P3 C18 C59 -171.5(5) . . . . ?
C219 P3 C18 C59 71.8(5) . . . . ?
C54 C16 C21 C61 1.9(10) . . . . ?
P4 C16 C21 C61 175.8(6) . . . . ?
C57 N7 C25 N6 0.7(8) . . . . ?
C57 N7 C25 C36 179.0(5) . . . . ?
C38 N6 C25 N7 -0.5(8) . . . . ?
Ir1 N6 C25 N7 -164.0(4) . . . . ?
C38 N6 C25 C36 -178.9(5) . . . . ?
Ir1 N6 C25 C36 17.6(5) . . . . ?
O3 P4 C30 C56 157.9(5) . . . . ?
N10 P4 C30 C56 28.1(5) . . . . ?
C16 P4 C30 C56 -88.3(5) . . . . ?
O3 P4 C30 C37 -23.6(5) . . . . ?
N10 P4 C30 C37 -153.5(4) . . . . ?
C16 P4 C30 C37 90.1(5) . . . . ?
C47 C29 C32 C63 3.5(8) . . . . ?
C47 C29 C32 C13 -173.9(5) . . . . ?
N8 C13 C32 C29 -4.1(8) . . . . ?
N9 C13 C32 C29 171.0(4) . . . . ?
N8 C13 C32 C63 178.3(5) . . . . ?
N9 C13 C32 C63 -6.5(7) . . . . ?
N7 C25 C36 C165 -9.5(8) . . . . ?
N6 C25 C36 C165 168.9(5) . . . . ?
N7 C25 C36 C170 176.0(5) . . . . ?
N6 C25 C36 C170 -5.6(7) . . . . ?
C56 C30 C37 C50 3.6(9) . . . . ?
P4 C30 C37 C50 -174.9(5) . . . . ?
C25 N6 C38 C49 1.8(8) . . . . ?
Ir1 N6 C38 C49 162.4(4) . . . . ?
C59 C18 C40 C62 -0.6(9) . . . . ?
P3 C18 C40 C62 175.7(5) . . . . ?
C56 C39 C44 C50 9.7(10) . . . . ?
C133 C15 C46 F19 -19.3(7) . . . . ?
C63 C15 C46 F19 166.3(5) . . . . ?
C133 C15 C46 F20 -139.3(5) . . . . ?
C63 C15 C46 F20 46.3(8) . . . . ?
C133 C15 C46 F21 99.7(6) . . . . ?
C63 C15 C46 F21 -74.7(6) . . . . ?
C32 C29 C47 C133 2.1(8) . . . . ?
C32 C29 C47 C226 -178.3(5) . . . . ?
C13 N8 C48 C51 0.2(9) . . . . ?
N6 C38 C49 C57 -3.2(9) . . . . ?
C30 C37 C50 C44 2.5(10) . . . . ?
C39 C44 C50 C37 -9.2(11) . . . . ?
N8 C48 C51 C221 1.2(10) . . . . ?
C21 C16 C54 C150 -1.0(10) . . . . ?
P4 C16 C54 C150 -175.2(6) . . . . ?
C44 C39 C56 C30 -3.5(11) . . . . ?
C37 C30 C56 C39 -3.1(9) . . . . ?
P4 C30 C56 C39 175.4(5) . . . . ?
C25 N7 C57 C49 -2.3(9) . . . . ?
C38 C49 C57 N7 3.6(10) . . . . ?
C167 C41 C59 C18 2.9(12) . . . . ?
C40 C18 C59 C41 -0.9(10) . . . . ?
P3 C18 C59 C41 -177.4(6) . . . . ?
C16 C21 C61 C151 -2.3(12) . . . . ?
C18 C40 C62 C167 0.3(10) . . . . ?
C29 C32 C63 C15 -8.5(8) . . . . ?
C13 C32 C63 C15 168.9(4) . . . . ?
C29 C32 C63 Ir1 172.4(4) . . . . ?
C13 C32 C63 Ir1 -10.2(6) . . . . ?
C133 C15 C63 C32 8.3(7) . . . . ?
C46 C15 C63 C32 -177.6(5) . . . . ?
C133 C15 C63 Ir1 -172.9(4) . . . . ?
C46 C15 C63 Ir1 1.2(8) . . . . ?
C170 Ir1 C63 C32 117.9(4) . . . . ?
N9 Ir1 C63 C32 16.2(3) . . . . ?
N6 Ir1 C63 C32 -157.9(3) . . . . ?
O3 Ir1 C63 C32 -26.8(16) . . . . ?
O4 Ir1 C63 C32 -71.4(4) . . . . ?
C170 Ir1 C63 C15 -60.9(5) . . . . ?
N9 Ir1 C63 C15 -162.7(5) . . . . ?
N6 Ir1 C63 C15 23.3(5) . . . . ?
O3 Ir1 C63 C15 154.4(12) . . . . ?
O4 Ir1 C63 C15 109.7(5) . . . . ?
C29 C47 C133 C15 -2.0(9) . . . . ?
C226 C47 C133 C15 178.4(5) . . . . ?
C63 C15 C133 C47 -3.6(8) . . . . ?
C46 C15 C133 C47 -178.1(5) . . . . ?
C170 C36 C165 C168 3.9(9) . . . . ?
C25 C36 C165 C168 -169.9(5) . . . . ?
C59 C41 C167 C62 -3.2(12) . . . . ?
C40 C62 C167 C41 1.6(11) . . . . ?
C36 C165 C168 C222 -3.5(8) . . . . ?
C36 C165 C168 C225 179.1(5) . . . . ?
C165 C36 C170 C210 -5.5(8) . . . . ?
C25 C36 C170 C210 168.6(5) . . . . ?
C165 C36 C170 Ir1 176.3(4) . . . . ?
C25 C36 C170 Ir1 -9.6(6) . . . . ?
C63 Ir1 C170 C210 -60.4(6) . . . . ?
N9 Ir1 C170 C210 23.1(6) . . . . ?
N6 Ir1 C170 C210 -162.8(6) . . . . ?
O3 Ir1 C170 C210 115.8(6) . . . . ?
O4 Ir1 C170 C210 170.1(6) . . . . ?
C63 Ir1 C170 C36 117.3(4) . . . . ?
N9 Ir1 C170 C36 -159.2(4) . . . . ?
N6 Ir1 C170 C36 14.9(4) . . . . ?
O3 Ir1 C170 C36 -66.5(4) . . . . ?
O4 Ir1 C170 C36 -12.2(11) . . . . ?
C217 C205 C206 C215 4.8(10) . . . . ?
C36 C170 C210 C222 7.1(8) . . . . ?
Ir1 C170 C210 C222 -175.2(4) . . . . ?
C36 C170 C210 C207 -177.6(5) . . . . ?
Ir1 C170 C210 C207 0.1(9) . . . . ?
F17 C207 C210 C222 -135.2(5) . . . . ?
F16 C207 C210 C222 -11.4(7) . . . . ?
F18 C207 C210 C222 106.7(6) . . . . ?
F17 C207 C210 C170 49.1(8) . . . . ?
F16 C207 C210 C170 173.0(5) . . . . ?
F18 C207 C210 C170 -68.9(7) . . . . ?
C205 C206 C215 C216 -6.0(11) . . . . ?
C206 C215 C216 C219 4.1(11) . . . . ?
C206 C205 C217 C219 -1.5(10) . . . . ?
C205 C217 C219 C216 -0.5(9) . . . . ?
C205 C217 C219 P3 -175.6(5) . . . . ?
C215 C216 C219 C217 -0.8(9) . . . . ?
C215 C216 C219 P3 174.2(5) . . . . ?
O4 P3 C219 C217 -161.9(5) . . . . ?
N10 P3 C219 C217 -33.5(5) . . . . ?
C18 P3 C219 C217 82.0(5) . . . . ?
O4 P3 C219 C216 23.4(5) . . . . ?
N10 P3 C219 C216 151.8(4) . . . . ?
C18 P3 C219 C216 -92.6(5) . . . . ?
C13 N9 C221 C51 1.8(8) . . . . ?
Ir1 N9 C221 C51 163.7(4) . . . . ?
C48 C51 C221 N9 -2.3(9) . . . . ?
C170 C210 C222 C168 -7.5(8) . . . . ?
C207 C210 C222 C168 176.7(5) . . . . ?
C165 C168 C222 C210 5.3(8) . . . . ?
C225 C168 C222 C210 -177.3(5) . . . . ?
C165 C168 C225 F15 -111.6(6) . . . . ?
C222 C168 C225 F15 71.1(6) . . . . ?
C165 C168 C225 F13 11.2(8) . . . . ?
C222 C168 C225 F13 -166.1(5) . . . . ?
C165 C168 C225 F14 128.3(6) . . . . ?
C222 C168 C225 F14 -49.0(7) . . . . ?
C133 C47 C226 F23 11.1(9) . . . . ?
C29 C47 C226 F23 -168.6(6) . . . . ?
C133 C47 C226 F24 131.9(7) . . . . ?
C29 C47 C226 F24 -47.7(9) . . . . ?
C133 C47 C226 F22 -109.3(7) . . . . ?
C29 C47 C226 F22 71.1(8) . . . . ?
C21 C61 C151 C150 1.8(13) . . . . ?
C61 C151 C150 C54 -1.0(12) . . . . ?
C16 C54 C150 C151 0.6(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         4.493
_refine_diff_density_min         -2.413
_refine_diff_density_rms         0.275
