# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

####################################################################### 
# 
# 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_xs48plt
_database_code_depnum_ccdc_archive 'CCDC 1010939'
_audit_update_record             
;
2014-06-28 deposited with the CCDC.
2014-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H33 F10 Ir N11 P'
_chemical_formula_weight         1128.98

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

_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                   9.5524(9)
_cell_length_b                   13.2533(12)
_cell_length_c                   18.9296(18)
_cell_angle_alpha                101.946(1)
_cell_angle_beta                 101.154(1)
_cell_angle_gamma                103.248(1)
_cell_volume                     2208.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5117
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    3.149
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.3808
_exptl_absorpt_correction_T_max  0.5442
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Siemens P4 X-ray diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15947
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.62
_reflns_number_total             9924
_reflns_number_gt                8655
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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. The crystallographic
 asymmetric unit contains three molecules of acetonitrile.  One of the
 three acetonitrile molecules was located and refined, whereas the other
 two were treated as diffuse electron density contributions with the aid 
 of the SQUEEZE routine in the program PLATON. Although specific positions
 for the independent carbon, nitrogen, and hydrogen atoms of these two 
 disordered molecules of acetonitrile were not determined, the calculated
 density, absorption coefficient and empirical formula weight reflect their
 presence within the crystal lattice.   
;

_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)+(0.0499P)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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9924
_refine_ls_number_parameters     551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_restrained_S_all      0.880
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P-1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.022 0.000 0.500 277 87 ' '
_platon_squeeze_details          
;
;
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 0.154521(12) 0.299829(8) 0.195073(6) 0.03746(5) Uani 1 1 d . . .
P1 P 0.16721(15) 0.70756(11) 0.43767(7) 0.0738(3) Uani 1 1 d . . .
F1 F 0.1984(4) 0.6135(3) 0.47208(18) 0.1029(10) Uani 1 1 d . . .
F2 F 0.1369(5) 0.8023(3) 0.4030(2) 0.1233(13) Uani 1 1 d . . .
F3 F 0.3277(4) 0.7320(4) 0.4231(3) 0.1395(15) Uani 1 1 d . . .
F4 F 0.1016(4) 0.6273(2) 0.35671(15) 0.1005(9) Uani 1 1 d . . .
F5 F 0.0074(4) 0.6812(4) 0.4521(2) 0.1249(13) Uani 1 1 d . . .
F6 F 0.2360(5) 0.7883(3) 0.51805(19) 0.1359(14) Uani 1 1 d . . .
F7 F 0.4905(3) 0.0802(2) 0.0579(2) 0.1061(11) Uani 1 1 d . . .
F8 F 0.5397(5) 1.0661(2) 0.2486(3) 0.1345(16) Uani 1 1 d . . .
F9 F -0.1704(3) -0.46530(18) 0.1501(2) 0.0999(10) Uani 1 1 d . . .
F10 F -0.1299(3) 0.39207(18) -0.05397(14) 0.0804(8) Uani 1 1 d . . .
N1 N 0.2649(3) 0.45313(19) 0.19922(15) 0.0400(5) Uani 1 1 d . . .
N2 N 0.3684(3) 0.45866(19) 0.16032(16) 0.0435(6) Uani 1 1 d . . .
N3 N 0.4343(3) 0.5578(2) 0.15958(18) 0.0499(7) Uani 1 1 d . . .
N4 N 0.0474(3) 0.14114(19) 0.17220(15) 0.0418(6) Uani 1 1 d . . .
N5 N -0.0447(3) 0.10013(19) 0.10379(16) 0.0433(6) Uani 1 1 d . . .
N6 N -0.1051(3) -0.0047(2) 0.08663(17) 0.0465(6) Uani 1 1 d . . .
N7 N 0.2730(3) 0.3112(2) 0.30567(16) 0.0446(6) Uani 1 1 d . . .
N8 N 0.0103(3) 0.3438(2) 0.26084(16) 0.0428(6) Uani 1 1 d . . .
N9 N 0.5785(9) 0.5462(6) 0.3430(5) 0.153(3) Uani 1 1 d . . .
C1 C 0.3106(3) 0.2712(2) 0.14110(18) 0.0416(7) Uani 1 1 d . . .
C2 C 0.3994(4) 0.3620(2) 0.12855(19) 0.0452(7) Uani 1 1 d . . .
C3 C 0.5101(4) 0.3621(3) 0.0920(2) 0.0617(9) Uani 1 1 d . . .
H3 H 0.5632 0.4254 0.0844 0.074 Uiso 1 1 calc R . .
C4 C 0.5414(5) 0.2646(3) 0.0662(3) 0.0697(11) Uani 1 1 d . . .
H4 H 0.6143 0.2607 0.0404 0.084 Uiso 1 1 calc R . .
C5 C 0.4591(5) 0.1746(3) 0.0809(3) 0.0680(11) Uani 1 1 d . . .
C6 C 0.3457(4) 0.1751(3) 0.1159(2) 0.0551(9) Uani 1 1 d . . .
H6 H 0.2920 0.1115 0.1228 0.066 Uiso 1 1 calc R . .
C7 C 0.2634(4) 0.5547(2) 0.22513(19) 0.0447(7) Uani 1 1 d . . .
H7 H 0.2026 0.5774 0.2542 0.054 Uiso 1 1 calc R . .
C8 C 0.3702(4) 0.6206(3) 0.2005(2) 0.0460(7) Uani 1 1 d . . .
C9 C 0.4154(4) 0.7385(3) 0.2138(2) 0.0534(9) Uani 1 1 d . . .
C10 C 0.3547(5) 0.8022(3) 0.2587(3) 0.0681(11) Uani 1 1 d . . .
H10 H 0.2840 0.7703 0.2810 0.082 Uiso 1 1 calc R . .
C11 C 0.3969(6) 0.9131(4) 0.2714(3) 0.0877(15) Uani 1 1 d . . .
H11 H 0.3571 0.9562 0.3025 0.105 Uiso 1 1 calc R . .
C12 C 0.4989(6) 0.9571(3) 0.2365(4) 0.0890(17) Uani 1 1 d . . .
C13 C 0.5621(5) 0.8973(3) 0.1917(4) 0.0867(16) Uani 1 1 d . . .
H13 H 0.6322 0.9298 0.1694 0.104 Uiso 1 1 calc R . .
C14 C 0.5194(5) 0.7863(3) 0.1802(3) 0.0709(12) Uani 1 1 d . . .
H14 H 0.5611 0.7439 0.1497 0.085 Uiso 1 1 calc R . .
C15 C 0.0177(3) 0.2783(2) 0.09346(18) 0.0387(6) Uani 1 1 d . . .
C16 C -0.0695(4) 0.1719(2) 0.05933(19) 0.0418(7) Uani 1 1 d . . .
C17 C -0.1690(4) 0.1371(3) -0.0094(2) 0.0487(8) Uani 1 1 d . . .
H17 H -0.2219 0.0650 -0.0290 0.058 Uiso 1 1 calc R . .
C18 C -0.1888(4) 0.2126(3) -0.0491(2) 0.0525(8) Uani 1 1 d . . .
H18 H -0.2541 0.1926 -0.0961 0.063 Uiso 1 1 calc R . .
C19 C -0.1079(4) 0.3178(3) -0.0158(2) 0.0513(8) Uani 1 1 d . . .
C20 C -0.0069(4) 0.3528(2) 0.0529(2) 0.0469(7) Uani 1 1 d . . .
H20 H 0.0444 0.4252 0.0723 0.056 Uiso 1 1 calc R . .
C21 C 0.0477(4) 0.0567(2) 0.2010(2) 0.0487(8) Uani 1 1 d . . .
H21 H 0.1012 0.0585 0.2481 0.058 Uiso 1 1 calc R . .
C22 C -0.0478(4) -0.0346(2) 0.1469(2) 0.0454(7) Uani 1 1 d . . .
C23 C -0.0854(4) -0.1484(3) 0.1483(2) 0.0499(8) Uani 1 1 d . . .
C24 C -0.1678(4) -0.2284(3) 0.0846(2) 0.0550(8) Uani 1 1 d . . .
H24 H -0.2037 -0.2103 0.0411 0.066 Uiso 1 1 calc R . .
C25 C -0.1969(5) -0.3356(3) 0.0856(3) 0.0634(10) Uani 1 1 d . . .
H25 H -0.2516 -0.3896 0.0429 0.076 Uiso 1 1 calc R . .
C26 C -0.1445(5) -0.3602(3) 0.1497(3) 0.0653(11) Uani 1 1 d . . .
C27 C -0.0660(6) -0.2844(3) 0.2144(3) 0.0822(15) Uani 1 1 d . . .
H27 H -0.0330 -0.3041 0.2577 0.099 Uiso 1 1 calc R . .
C28 C -0.0367(5) -0.1762(3) 0.2138(3) 0.0717(12) Uani 1 1 d . . .
H28 H 0.0156 -0.1227 0.2572 0.086 Uiso 1 1 calc R . .
C29 C -0.1241(4) 0.3562(3) 0.2343(2) 0.0526(8) Uani 1 1 d . . .
H29 H -0.1592 0.3444 0.1831 0.063 Uiso 1 1 calc R . .
C30 C -0.2121(5) 0.3861(4) 0.2803(3) 0.0677(11) Uani 1 1 d . . .
H30 H -0.3047 0.3939 0.2604 0.081 Uiso 1 1 calc R . .
C31 C -0.1609(5) 0.4036(4) 0.3547(3) 0.0742(12) Uani 1 1 d . . .
H31 H -0.2178 0.4250 0.3865 0.089 Uiso 1 1 calc R . .
C32 C -0.0243(5) 0.3900(3) 0.3837(2) 0.0647(10) Uani 1 1 d . . .
H32 H 0.0100 0.4000 0.4348 0.078 Uiso 1 1 calc R . .
C33 C 0.0606(4) 0.3612(3) 0.33569(19) 0.0477(7) Uani 1 1 d . . .
C34 C 0.2090(4) 0.3450(3) 0.3602(2) 0.0513(8) Uani 1 1 d . . .
C35 C 0.2811(5) 0.3623(4) 0.4350(2) 0.0748(12) Uani 1 1 d . . .
H35 H 0.2392 0.3893 0.4726 0.090 Uiso 1 1 calc R . .
C36 C 0.4153(6) 0.3389(4) 0.4528(3) 0.0830(14) Uani 1 1 d . . .
H36 H 0.4648 0.3499 0.5024 0.100 Uiso 1 1 calc R . .
C37 C 0.4747(5) 0.2988(4) 0.3958(3) 0.0772(13) Uani 1 1 d . . .
H37 H 0.5624 0.2792 0.4064 0.093 Uiso 1 1 calc R . .
C38 C 0.4031(4) 0.2881(3) 0.3234(2) 0.0577(9) Uani 1 1 d . . .
H38 H 0.4458 0.2641 0.2854 0.069 Uiso 1 1 calc R . .
C39 C 0.6363(9) 0.6287(8) 0.3543(4) 0.111(2) Uani 1 1 d . . .
C40 C 0.7097(10) 0.7460(8) 0.3733(6) 0.181(4) Uani 1 1 d . . .
H40A H 0.6393 0.7849 0.3832 0.271 Uiso 1 1 calc R . .
H40B H 0.7460 0.7633 0.3321 0.271 Uiso 1 1 calc R . .
H40C H 0.7913 0.7655 0.4167 0.271 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 C1 2.024(3) . ?
Ir1 C15 2.030(3) . ?
Ir1 N4 2.031(2) . ?
Ir1 N1 2.041(2) . ?
Ir1 N8 2.126(3) . ?
Ir1 N7 2.136(3) . ?
P1 F5 1.576(4) . ?
P1 F1 1.581(3) . ?
P1 F3 1.582(4) . ?
P1 F6 1.584(3) . ?
P1 F4 1.588(3) . ?
P1 F2 1.589(3) . ?
F7 C5 1.358(4) . ?
F8 C12 1.364(5) . ?
F9 C26 1.360(4) . ?
F10 C19 1.366(4) . ?
N1 C7 1.338(4) . ?
N1 N2 1.341(4) . ?
N2 N3 1.324(3) . ?
N2 C2 1.419(4) . ?
N3 C8 1.348(4) . ?
N4 N5 1.340(4) . ?
N4 C21 1.342(4) . ?
N5 N6 1.320(4) . ?
N5 C16 1.424(4) . ?
N6 C22 1.342(4) . ?
N7 C38 1.344(4) . ?
N7 C34 1.348(5) . ?
N8 C29 1.345(4) . ?
N8 C33 1.357(4) . ?
N9 C39 1.062(10) . ?
C1 C2 1.397(4) . ?
C1 C6 1.403(4) . ?
C2 C3 1.371(5) . ?
C3 C4 1.404(5) . ?
C4 C5 1.381(6) . ?
C5 C6 1.375(5) . ?
C7 C8 1.403(5) . ?
C8 C9 1.476(4) . ?
C9 C10 1.375(6) . ?
C9 C14 1.384(6) . ?
C10 C11 1.388(6) . ?
C11 C12 1.369(8) . ?
C12 C13 1.360(8) . ?
C13 C14 1.392(5) . ?
C15 C20 1.403(4) . ?
C15 C16 1.406(4) . ?
C16 C17 1.371(5) . ?
C17 C18 1.395(5) . ?
C18 C19 1.375(5) . ?
C19 C20 1.378(5) . ?
C21 C22 1.402(5) . ?
C22 C23 1.476(4) . ?
C23 C24 1.385(5) . ?
C23 C28 1.390(5) . ?
C24 C25 1.388(5) . ?
C25 C26 1.353(6) . ?
C26 C27 1.365(7) . ?
C27 C28 1.400(5) . ?
C29 C30 1.384(5) . ?
C30 C31 1.349(6) . ?
C31 C32 1.382(6) . ?
C32 C33 1.384(5) . ?
C33 C34 1.482(5) . ?
C34 C35 1.396(5) . ?
C35 C36 1.382(6) . ?
C36 C37 1.380(7) . ?
C37 C38 1.370(6) . ?
C39 C40 1.486(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ir1 C15 87.30(13) . . ?
C1 Ir1 N4 92.97(11) . . ?
C15 Ir1 N4 79.94(11) . . ?
C1 Ir1 N1 79.68(11) . . ?
C15 Ir1 N1 92.84(11) . . ?
N4 Ir1 N1 169.99(10) . . ?
C1 Ir1 N8 173.55(10) . . ?
C15 Ir1 N8 97.56(11) . . ?
N4 Ir1 N8 92.07(10) . . ?
N1 Ir1 N8 95.77(10) . . ?
C1 Ir1 N7 98.59(12) . . ?
C15 Ir1 N7 172.38(10) . . ?
N4 Ir1 N7 94.86(10) . . ?
N1 Ir1 N7 92.98(10) . . ?
N8 Ir1 N7 76.95(10) . . ?
F5 P1 F1 89.1(2) . . ?
F5 P1 F3 179.0(3) . . ?
F1 P1 F3 90.1(2) . . ?
F5 P1 F6 91.6(2) . . ?
F1 P1 F6 89.0(2) . . ?
F3 P1 F6 88.8(3) . . ?
F5 P1 F4 89.6(2) . . ?
F1 P1 F4 91.13(18) . . ?
F3 P1 F4 90.0(2) . . ?
F6 P1 F4 178.8(3) . . ?
F5 P1 F2 91.3(2) . . ?
F1 P1 F2 179.7(2) . . ?
F3 P1 F2 89.6(2) . . ?
F6 P1 F2 91.0(2) . . ?
F4 P1 F2 88.90(18) . . ?
C7 N1 N2 105.5(2) . . ?
C7 N1 Ir1 140.6(2) . . ?
N2 N1 Ir1 113.68(18) . . ?
N3 N2 N1 113.7(2) . . ?
N3 N2 C2 128.1(3) . . ?
N1 N2 C2 118.2(2) . . ?
N2 N3 C8 104.9(3) . . ?
N5 N4 C21 105.2(2) . . ?
N5 N4 Ir1 114.08(18) . . ?
C21 N4 Ir1 140.3(2) . . ?
N6 N5 N4 114.1(2) . . ?
N6 N5 C16 127.7(3) . . ?
N4 N5 C16 118.2(2) . . ?
N5 N6 C22 104.7(3) . . ?
C38 N7 C34 119.6(3) . . ?
C38 N7 Ir1 125.0(3) . . ?
C34 N7 Ir1 115.4(2) . . ?
C29 N8 C33 118.3(3) . . ?
C29 N8 Ir1 125.4(2) . . ?
C33 N8 Ir1 116.3(2) . . ?
C2 C1 C6 115.0(3) . . ?
C2 C1 Ir1 114.8(2) . . ?
C6 C1 Ir1 130.2(3) . . ?
C3 C2 C1 125.3(3) . . ?
C3 C2 N2 121.5(3) . . ?
C1 C2 N2 113.2(3) . . ?
C2 C3 C4 118.6(4) . . ?
C5 C4 C3 117.1(3) . . ?
F7 C5 C6 118.5(4) . . ?
F7 C5 C4 117.8(4) . . ?
C6 C5 C4 123.7(3) . . ?
C5 C6 C1 120.3(3) . . ?
N1 C7 C8 107.5(3) . . ?
N3 C8 C7 108.5(3) . . ?
N3 C8 C9 121.6(3) . . ?
C7 C8 C9 130.0(3) . . ?
C10 C9 C14 119.1(3) . . ?
C10 C9 C8 121.0(4) . . ?
C14 C9 C8 119.9(4) . . ?
C9 C10 C11 121.1(4) . . ?
C12 C11 C10 117.9(5) . . ?
C13 C12 F8 119.2(5) . . ?
C13 C12 C11 123.0(4) . . ?
F8 C12 C11 117.9(5) . . ?
C12 C13 C14 118.3(4) . . ?
C9 C14 C13 120.5(4) . . ?
C20 C15 C16 115.0(3) . . ?
C20 C15 Ir1 130.5(2) . . ?
C16 C15 Ir1 114.5(2) . . ?
C17 C16 C15 125.4(3) . . ?
C17 C16 N5 121.6(3) . . ?
C15 C16 N5 112.9(3) . . ?
C16 C17 C18 118.3(3) . . ?
C19 C18 C17 117.3(3) . . ?
F10 C19 C18 117.3(3) . . ?
F10 C19 C20 118.2(3) . . ?
C18 C19 C20 124.5(3) . . ?
C19 C20 C15 119.4(3) . . ?
N4 C21 C22 107.2(3) . . ?
N6 C22 C21 108.8(3) . . ?
N6 C22 C23 121.1(3) . . ?
C21 C22 C23 130.0(3) . . ?
C24 C23 C28 119.5(3) . . ?
C24 C23 C22 120.5(3) . . ?
C28 C23 C22 120.0(3) . . ?
C23 C24 C25 120.2(4) . . ?
C26 C25 C24 118.9(4) . . ?
C25 C26 F9 118.9(4) . . ?
C25 C26 C27 123.2(3) . . ?
F9 C26 C27 117.9(4) . . ?
C26 C27 C28 118.1(4) . . ?
C23 C28 C27 120.1(4) . . ?
N8 C29 C30 122.6(4) . . ?
C31 C30 C29 118.7(4) . . ?
C30 C31 C32 120.3(4) . . ?
C31 C32 C33 119.0(4) . . ?
N8 C33 C32 121.1(3) . . ?
N8 C33 C34 114.9(3) . . ?
C32 C33 C34 124.0(3) . . ?
N7 C34 C35 120.5(4) . . ?
N7 C34 C33 116.3(3) . . ?
C35 C34 C33 123.2(4) . . ?
C36 C35 C34 119.4(4) . . ?
C37 C36 C35 119.0(4) . . ?
C38 C37 C36 119.3(4) . . ?
N7 C38 C37 122.1(4) . . ?
N9 C39 C40 176.0(11) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         1.395
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.088
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_xs3ccd
_database_code_depnum_ccdc_archive 'CCDC 1012360'
_audit_update_record             
;
2014-07-06 deposited with the CCDC.
2014-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H23 F2 Ir N8 O'
_chemical_formula_weight         789.80

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'
Ir Ir -1.4442 7.9887 '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                   11.0054(12)
_cell_length_b                   14.2851(15)
_cell_length_c                   21.789(2)
_cell_angle_alpha                71.698(2)
_cell_angle_beta                 89.997(2)
_cell_angle_gamma                67.306(2)
_cell_volume                     2971.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5447
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.50

_exptl_crystal_description       ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544
_exptl_absorpt_coefficient_mu    4.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_T_max  0.68
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            21475
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         0.99
_diffrn_reflns_theta_max         27.50
_reflns_number_total             13291
_reflns_number_gt                9619
_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)+(0.0311P)²+1.1883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13291
_refine_ls_number_parameters     829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.309850(13) 0.873029(11) 0.445079(7) 0.03203(5) Uani 1 1 d . . .
Ir2 Ir 0.182872(13) 0.126976(11) 0.054908(7) 0.03225(5) Uani 1 1 d . . .
F1 F 0.1034(3) 0.5743(2) 0.54812(15) 0.0705(8) Uani 1 1 d . . .
F2 F 0.7333(3) 0.7256(2) 0.63489(13) 0.0658(8) Uani 1 1 d . . .
F3 F 0.4591(3) 0.2742(2) -0.13476(13) 0.0662(8) Uani 1 1 d . . .
F4 F -0.3229(2) 0.4256(2) -0.04786(14) 0.0703(8) Uani 1 1 d . . .
O1 O 0.0597(3) 1.1218(3) 0.28020(14) 0.0543(8) Uani 1 1 d . . .
O2 O 0.1815(3) -0.1222(3) 0.22028(14) 0.0554(8) Uani 1 1 d . . .
N1 N 0.2406(3) 0.9677(3) 0.50129(15) 0.0328(7) Uani 1 1 d . . .
N2 N 0.1831(3) 0.9263(3) 0.55077(15) 0.0378(7) Uani 1 1 d . . .
N3 N 0.1409(3) 0.9842(3) 0.58895(16) 0.0421(8) Uani 1 1 d . . .
N4 N 0.3785(3) 0.7562(3) 0.40510(15) 0.0354(7) Uani 1 1 d . . .
N5 N 0.4904(3) 0.6705(3) 0.43852(15) 0.0369(7) Uani 1 1 d . . .
N6 N 0.5235(3) 0.5884(3) 0.41679(16) 0.0432(8) Uani 1 1 d . . .
N7 N 0.1448(3) 0.9741(3) 0.37415(16) 0.0389(8) Uani 1 1 d . . .
H7 H 0.0721 0.9649 0.3778 0.047 Uiso 1 1 calc R . .
N8 N 0.3806(3) 0.9766(3) 0.37429(15) 0.0355(7) Uani 1 1 d . . .
N9 N 0.1352(3) 0.2435(3) 0.09501(15) 0.0347(7) Uani 1 1 d . . .
N10 N 0.1614(3) 0.3287(3) 0.06198(15) 0.0372(7) Uani 1 1 d . . .
N11 N 0.1118(3) 0.4116(3) 0.08298(15) 0.0408(8) Uani 1 1 d . . .
N12 N 0.2081(3) 0.0320(3) -0.00126(15) 0.0341(7) Uani 1 1 d . . .
N13 N 0.1094(3) 0.0731(3) -0.05060(15) 0.0379(7) Uani 1 1 d . . .
N14 N 0.1253(3) 0.0156(3) -0.08885(16) 0.0419(8) Uani 1 1 d . . .
N15 N 0.1189(3) 0.0259(3) 0.12607(16) 0.0398(8) Uani 1 1 d . . .
H15 H 0.0367 0.0357 0.1226 0.048 Uiso 1 1 calc R . .
N16 N 0.3565(3) 0.0234(3) 0.12562(15) 0.0345(7) Uani 1 1 d . . .
C1 C 0.2343(4) 1.0591(3) 0.5077(2) 0.0378(9) Uani 1 1 d . . .
H1 H 0.2653 1.1073 0.4806 0.045 Uiso 1 1 calc R . .
C2 C 0.1707(4) 1.0694(3) 0.5640(2) 0.0389(9) Uani 1 1 d . . .
C3 C 0.1363(4) 1.1516(4) 0.5956(2) 0.0461(10) Uani 1 1 d . . .
C4 C 0.1511(5) 1.2472(4) 0.5661(3) 0.0658(15) Uani 1 1 d . . .
H4 H 0.1856 1.2592 0.5268 0.079 Uiso 1 1 calc R . .
C5 C 0.1136(7) 1.3250(5) 0.5962(3) 0.0825(19) Uani 1 1 d . . .
H5 H 0.1234 1.3891 0.5766 0.099 Uiso 1 1 calc R . .
C6 C 0.0629(6) 1.3091(5) 0.6537(3) 0.0834(19) Uani 1 1 d . . .
H6 H 0.0364 1.3626 0.6727 0.100 Uiso 1 1 calc R . .
C7 C 0.0514(5) 1.2127(5) 0.6836(3) 0.0728(16) Uani 1 1 d . . .
H7A H 0.0184 1.2005 0.7233 0.087 Uiso 1 1 calc R . .
C8 C 0.0887(4) 1.1345(4) 0.6546(2) 0.0548(12) Uani 1 1 d . . .
H8 H 0.0816 1.0695 0.6752 0.066 Uiso 1 1 calc R . .
C9 C 0.1636(4) 0.8332(3) 0.55393(19) 0.0368(8) Uani 1 1 d . . .
C10 C 0.0929(4) 0.7925(4) 0.5997(2) 0.0445(10) Uani 1 1 d . . .
H10 H 0.0608 0.8235 0.6313 0.053 Uiso 1 1 calc R . .
C11 C 0.0715(4) 0.7051(4) 0.5971(2) 0.0502(11) Uani 1 1 d . . .
H11 H 0.0232 0.6760 0.6263 0.060 Uiso 1 1 calc R . .
C12 C 0.1237(4) 0.6625(4) 0.5501(2) 0.0472(10) Uani 1 1 d . . .
C13 C 0.1957(4) 0.7007(3) 0.5052(2) 0.0438(10) Uani 1 1 d . . .
H13 H 0.2293 0.6672 0.4749 0.053 Uiso 1 1 calc R . .
C14 C 0.2181(4) 0.7910(3) 0.50549(18) 0.0356(8) Uani 1 1 d . . .
C15 C 0.3357(4) 0.7268(3) 0.35980(18) 0.0359(8) Uani 1 1 d . . .
H15A H 0.2599 0.7683 0.3291 0.043 Uiso 1 1 calc R . .
C16 C 0.4260(4) 0.6222(3) 0.36699(19) 0.0409(9) Uani 1 1 d . . .
C17 C 0.4225(4) 0.5523(3) 0.33031(19) 0.0428(10) Uani 1 1 d . . .
C18 C 0.3139(5) 0.5846(4) 0.2847(2) 0.0605(12) Uani 1 1 d . . .
H18 H 0.2453 0.6526 0.2753 0.073 Uiso 1 1 calc R . .
C19 C 0.3065(6) 0.5167(5) 0.2530(2) 0.0682(14) Uani 1 1 d . . .
H19 H 0.2318 0.5381 0.2236 0.082 Uiso 1 1 calc R . .
C20 C 0.4101(6) 0.4171(5) 0.2650(3) 0.0729(16) Uani 1 1 d . . .
H20 H 0.4061 0.3719 0.2430 0.087 Uiso 1 1 calc R . .
C21 C 0.5188(6) 0.3852(4) 0.3093(3) 0.0662(14) Uani 1 1 d . . .
H21 H 0.5886 0.3183 0.3171 0.079 Uiso 1 1 calc R . .
C22 C 0.5262(5) 0.4513(4) 0.3428(2) 0.0528(11) Uani 1 1 d . . .
H22 H 0.5998 0.4285 0.3733 0.063 Uiso 1 1 calc R . .
C23 C 0.5554(4) 0.6785(3) 0.49144(18) 0.0360(8) Uani 1 1 d . . .
C24 C 0.6754(4) 0.5988(4) 0.5254(2) 0.0449(10) Uani 1 1 d . . .
H24 H 0.7151 0.5362 0.5152 0.054 Uiso 1 1 calc R . .
C25 C 0.7354(5) 0.6141(4) 0.5749(2) 0.0503(11) Uani 1 1 d . . .
H25 H 0.8162 0.5622 0.5991 0.060 Uiso 1 1 calc R . .
C26 C 0.6710(4) 0.7092(4) 0.5871(2) 0.0472(10) Uani 1 1 d . . .
C27 C 0.5517(4) 0.7864(3) 0.55475(19) 0.0406(9) Uani 1 1 d . . .
H27 H 0.5131 0.8482 0.5659 0.049 Uiso 1 1 calc R . .
C28 C 0.4850(4) 0.7745(3) 0.50412(18) 0.0351(8) Uani 1 1 d . . .
C29 C 0.1508(4) 1.0520(4) 0.3239(2) 0.0406(9) Uani 1 1 d . . .
C30 C 0.2880(4) 1.0513(3) 0.32351(18) 0.0363(8) Uani 1 1 d . . .
C31 C 0.3191(4) 1.1234(4) 0.2739(2) 0.0474(10) Uani 1 1 d . . .
H31 H 0.2539 1.1751 0.2395 0.057 Uiso 1 1 calc R . .
C32 C 0.4461(5) 1.1187(4) 0.2753(2) 0.0517(11) Uani 1 1 d . . .
H32 H 0.4675 1.1671 0.2423 0.062 Uiso 1 1 calc R . .
C33 C 0.5405(4) 1.0421(4) 0.3261(2) 0.0501(11) Uani 1 1 d . . .
H33 H 0.6274 1.0368 0.3278 0.060 Uiso 1 1 calc R . .
C34 C 0.5048(4) 0.9724(4) 0.3748(2) 0.0432(9) Uani 1 1 d . . .
H34 H 0.5694 0.9205 0.4093 0.052 Uiso 1 1 calc R . .
C35 C 0.0620(4) 0.2733(3) 0.13999(18) 0.0357(8) Uani 1 1 d . . .
H35 H 0.0271 0.2320 0.1704 0.043 Uiso 1 1 calc R . .
C36 C 0.0477(4) 0.3779(3) 0.13280(18) 0.0384(9) Uani 1 1 d . . .
C37 C -0.0254(4) 0.4484(4) 0.16935(19) 0.0425(9) Uani 1 1 d . . .
C38 C -0.1014(5) 0.4154(4) 0.2152(2) 0.0590(12) Uani 1 1 d . . .
H38 H -0.1016 0.3473 0.2247 0.071 Uiso 1 1 calc R . .
C39 C -0.1770(5) 0.4837(5) 0.2470(2) 0.0692(15) Uani 1 1 d . . .
H39 H -0.2306 0.4626 0.2764 0.083 Uiso 1 1 calc R . .
C40 C -0.1730(5) 0.5828(5) 0.2349(2) 0.0723(16) Uani 1 1 d . . .
H40 H -0.2224 0.6282 0.2568 0.087 Uiso 1 1 calc R . .
C41 C -0.0960(5) 0.6148(4) 0.1906(3) 0.0644(14) Uani 1 1 d . . .
H41 H -0.0936 0.6818 0.1828 0.077 Uiso 1 1 calc R . .
C42 C -0.0221(5) 0.5490(4) 0.1574(2) 0.0537(12) Uani 1 1 d . . .
H42 H 0.0296 0.5717 0.1274 0.064 Uiso 1 1 calc R . .
C43 C 0.2340(4) 0.3217(3) 0.00820(18) 0.0375(9) Uani 1 1 d . . .
C44 C 0.2759(4) 0.4004(4) -0.0247(2) 0.0448(10) Uani 1 1 d . . .
H44 H 0.2553 0.4619 -0.0134 0.054 Uiso 1 1 calc R . .
C45 C 0.3497(5) 0.3858(4) -0.0750(2) 0.0513(11) Uani 1 1 d . . .
H45 H 0.3775 0.4381 -0.0998 0.062 Uiso 1 1 calc R . .
C46 C 0.3801(4) 0.2906(4) -0.0870(2) 0.0469(11) Uani 1 1 d . . .
C47 C 0.3381(4) 0.2137(3) -0.05426(19) 0.0399(9) Uani 1 1 d . . .
H47 H 0.3617 0.1515 -0.0651 0.048 Uiso 1 1 calc R . .
C48 C 0.2597(4) 0.2261(3) -0.00438(18) 0.0359(8) Uani 1 1 d . . .
C49 C 0.2937(4) -0.0595(3) -0.0080(2) 0.0392(9) Uani 1 1 d . . .
H49 H 0.3733 -0.1076 0.0188 0.047 Uiso 1 1 calc R . .
C50 C 0.2404(4) -0.0696(3) -0.0638(2) 0.0390(9) Uani 1 1 d . . .
C51 C 0.2880(4) -0.1520(4) -0.0954(2) 0.0417(10) Uani 1 1 d . . .
C52 C 0.3990(5) -0.2479(4) -0.0657(3) 0.0635(14) Uani 1 1 d . . .
H52 H 0.4457 -0.2600 -0.0264 0.076 Uiso 1 1 calc R . .
C53 C 0.4384(6) -0.3253(5) -0.0961(3) 0.0815(19) Uani 1 1 d . . .
H53 H 0.5123 -0.3897 -0.0764 0.098 Uiso 1 1 calc R . .
C54 C 0.3725(7) -0.3097(5) -0.1533(3) 0.0829(19) Uani 1 1 d . . .
H54 H 0.3994 -0.3633 -0.1722 0.099 Uiso 1 1 calc R . .
C55 C 0.2647(6) -0.2130(5) -0.1833(3) 0.0758(17) Uani 1 1 d . . .
H55 H 0.2198 -0.2008 -0.2231 0.091 Uiso 1 1 calc R . .
C56 C 0.2234(5) -0.1348(4) -0.1547(2) 0.0588(13) Uani 1 1 d . . .
H56 H 0.1513 -0.0697 -0.1754 0.071 Uiso 1 1 calc R . .
C57 C -0.0038(4) 0.1676(3) -0.05412(19) 0.0375(9) Uani 1 1 d . . .
C58 C -0.1143(4) 0.2073(4) -0.0993(2) 0.0454(10) Uani 1 1 d . . .
H58 H -0.1155 0.1757 -0.1305 0.055 Uiso 1 1 calc R . .
C59 C -0.2243(4) 0.2961(4) -0.0969(2) 0.0496(11) Uani 1 1 d . . .
H59 H -0.3017 0.3257 -0.1262 0.060 Uiso 1 1 calc R . .
C60 C -0.2140(4) 0.3377(3) -0.0501(2) 0.0466(10) Uani 1 1 d . . .
C61 C -0.1038(4) 0.2994(3) -0.0057(2) 0.0435(10) Uani 1 1 d . . .
H61 H -0.1037 0.3333 0.0244 0.052 Uiso 1 1 calc R . .
C62 C 0.0095(4) 0.2089(3) -0.00528(18) 0.0326(8) Uani 1 1 d . . .
C63 C 0.2025(4) -0.0526(3) 0.1762(2) 0.0403(9) Uani 1 1 d . . .
C64 C 0.3394(4) -0.0517(3) 0.17663(18) 0.0376(9) Uani 1 1 d . . .
C65 C 0.4419(4) -0.1236(4) 0.2260(2) 0.0479(10) Uani 1 1 d . . .
H65 H 0.4284 -0.1756 0.2601 0.057 Uiso 1 1 calc R . .
C66 C 0.5640(4) -0.1188(4) 0.2250(2) 0.0513(11) Uani 1 1 d . . .
H66 H 0.6331 -0.1665 0.2585 0.062 Uiso 1 1 calc R . .
C67 C 0.5829(4) -0.0429(4) 0.1741(2) 0.0507(11) Uani 1 1 d . . .
H67 H 0.6651 -0.0387 0.1723 0.061 Uiso 1 1 calc R . .
C68 C 0.4773(4) 0.0278(4) 0.1250(2) 0.0429(9) Uani 1 1 d . . .
H68 H 0.4899 0.0800 0.0906 0.051 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 N4 2.014(3) . ?
Ir1 C14 2.017(4) . ?
Ir1 C28 2.030(4) . ?
Ir1 N1 2.039(3) . ?
Ir1 N7 2.085(3) . ?
Ir1 N8 2.152(3) . ?
Ir2 C62 2.011(4) . ?
Ir2 N9 2.013(3) . ?
Ir2 C48 2.040(4) . ?
Ir2 N12 2.041(3) . ?
Ir2 N15 2.089(3) . ?
Ir2 N16 2.145(3) . ?
F1 C12 1.375(5) . ?
F2 C26 1.373(5) . ?
F3 C46 1.375(4) . ?
F4 C60 1.377(4) . ?
O1 C29 1.240(5) . ?
O2 C63 1.242(5) . ?
N1 C1 1.331(5) . ?
N1 N2 1.343(4) . ?
N2 N3 1.315(4) . ?
N2 C9 1.408(5) . ?
N3 C2 1.332(5) . ?
N4 C15 1.336(5) . ?
N4 N5 1.350(4) . ?
N5 N6 1.323(4) . ?
N5 C23 1.414(5) . ?
N6 C16 1.354(5) . ?
N7 C29 1.317(5) . ?
N8 C34 1.345(5) . ?
N8 C30 1.350(5) . ?
N9 C35 1.337(4) . ?
N9 N10 1.342(4) . ?
N10 N11 1.324(4) . ?
N10 C43 1.426(4) . ?
N11 C36 1.358(5) . ?
N12 C49 1.338(5) . ?
N12 N13 1.339(4) . ?
N13 N14 1.312(4) . ?
N13 C57 1.420(5) . ?
N14 C50 1.333(5) . ?
N15 C63 1.315(5) . ?
N16 C64 1.352(5) . ?
N16 C68 1.356(5) . ?
C1 C2 1.431(5) . ?
C2 C3 1.472(5) . ?
C3 C8 1.372(6) . ?
C3 C4 1.387(7) . ?
C4 C5 1.392(7) . ?
C5 C6 1.360(8) . ?
C6 C7 1.382(8) . ?
C7 C8 1.381(6) . ?
C9 C10 1.386(5) . ?
C9 C14 1.399(5) . ?
C10 C11 1.374(6) . ?
C11 C12 1.367(6) . ?
C12 C13 1.372(6) . ?
C13 C14 1.406(5) . ?
C15 C16 1.397(5) . ?
C16 C17 1.472(5) . ?
C17 C18 1.384(6) . ?
C17 C22 1.393(6) . ?
C18 C19 1.379(6) . ?
C19 C20 1.381(7) . ?
C20 C21 1.369(8) . ?
C21 C22 1.386(7) . ?
C23 C24 1.378(5) . ?
C23 C28 1.406(5) . ?
C24 C25 1.381(6) . ?
C25 C26 1.380(6) . ?
C26 C27 1.353(6) . ?
C27 C28 1.414(5) . ?
C29 C30 1.506(5) . ?
C30 C31 1.386(6) . ?
C31 C32 1.373(6) . ?
C32 C33 1.365(6) . ?
C33 C34 1.381(6) . ?
C35 C36 1.397(5) . ?
C36 C37 1.474(5) . ?
C37 C38 1.389(6) . ?
C37 C42 1.394(6) . ?
C38 C39 1.385(6) . ?
C39 C40 1.375(7) . ?
C40 C41 1.370(7) . ?
C41 C42 1.380(6) . ?
C43 C44 1.372(6) . ?
C43 C48 1.398(5) . ?
C44 C45 1.386(6) . ?
C45 C46 1.379(6) . ?
C46 C47 1.352(6) . ?
C47 C48 1.400(5) . ?
C49 C50 1.420(5) . ?
C50 C51 1.472(5) . ?
C51 C56 1.379(6) . ?
C51 C52 1.393(6) . ?
C52 C53 1.393(7) . ?
C53 C54 1.354(9) . ?
C54 C55 1.383(8) . ?
C55 C56 1.376(6) . ?
C57 C58 1.373(5) . ?
C57 C62 1.401(5) . ?
C58 C59 1.390(6) . ?
C59 C60 1.356(6) . ?
C60 C61 1.365(6) . ?
C61 C62 1.406(5) . ?
C63 C64 1.511(5) . ?
C64 C65 1.378(6) . ?
C65 C66 1.371(6) . ?
C66 C67 1.367(6) . ?
C67 C68 1.389(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
N4 Ir1 C14 90.20(14) . . ?
N4 Ir1 C28 79.51(14) . . ?
C14 Ir1 C28 89.74(15) . . ?
N4 Ir1 N1 168.82(12) . . ?
C14 Ir1 N1 79.89(14) . . ?
C28 Ir1 N1 95.15(14) . . ?
N4 Ir1 N7 95.90(13) . . ?
C14 Ir1 N7 96.40(14) . . ?
C28 Ir1 N7 172.37(12) . . ?
N1 Ir1 N7 90.39(13) . . ?
N4 Ir1 N8 92.70(12) . . ?
C14 Ir1 N8 172.10(13) . . ?
C28 Ir1 N8 98.01(13) . . ?
N1 Ir1 N8 97.80(12) . . ?
N7 Ir1 N8 75.99(13) . . ?
C62 Ir2 N9 90.33(14) . . ?
C62 Ir2 C48 89.71(15) . . ?
N9 Ir2 C48 79.40(14) . . ?
C62 Ir2 N12 79.88(14) . . ?
N9 Ir2 N12 168.98(13) . . ?
C48 Ir2 N12 95.37(14) . . ?
C62 Ir2 N15 96.44(14) . . ?
N9 Ir2 N15 95.82(13) . . ?
C48 Ir2 N15 172.26(13) . . ?
N12 Ir2 N15 90.34(13) . . ?
C62 Ir2 N16 171.94(13) . . ?
N9 Ir2 N16 92.56(12) . . ?
C48 Ir2 N16 98.20(13) . . ?
N12 Ir2 N16 97.81(12) . . ?
N15 Ir2 N16 75.80(12) . . ?
C1 N1 N2 105.1(3) . . ?
C1 N1 Ir1 141.7(3) . . ?
N2 N1 Ir1 113.1(2) . . ?
N3 N2 N1 114.4(3) . . ?
N3 N2 C9 126.6(3) . . ?
N1 N2 C9 118.7(3) . . ?
N2 N3 C2 105.4(3) . . ?
C15 N4 N5 105.4(3) . . ?
C15 N4 Ir1 138.6(3) . . ?
N5 N4 Ir1 114.9(2) . . ?
N6 N5 N4 113.9(3) . . ?
N6 N5 C23 128.6(3) . . ?
N4 N5 C23 117.4(3) . . ?
N5 N6 C16 104.2(3) . . ?
C29 N7 Ir1 120.7(3) . . ?
C34 N8 C30 118.2(3) . . ?
C34 N8 Ir1 127.4(3) . . ?
C30 N8 Ir1 114.4(3) . . ?
C35 N9 N10 105.3(3) . . ?
C35 N9 Ir2 138.4(3) . . ?
N10 N9 Ir2 115.0(2) . . ?
N11 N10 N9 114.5(3) . . ?
N11 N10 C43 127.7(3) . . ?
N9 N10 C43 117.7(3) . . ?
N10 N11 C36 103.6(3) . . ?
C49 N12 N13 104.8(3) . . ?
C49 N12 Ir2 141.8(3) . . ?
N13 N12 Ir2 113.3(2) . . ?
N14 N13 N12 114.6(3) . . ?
N14 N13 C57 126.6(3) . . ?
N12 N13 C57 118.6(3) . . ?
N13 N14 C50 105.2(3) . . ?
C63 N15 Ir2 121.0(3) . . ?
C64 N16 C68 118.0(3) . . ?
C64 N16 Ir2 114.9(2) . . ?
C68 N16 Ir2 127.0(3) . . ?
N1 C1 C2 107.2(3) . . ?
N3 C2 C1 107.9(3) . . ?
N3 C2 C3 119.4(3) . . ?
C1 C2 C3 132.7(4) . . ?
C8 C3 C4 119.5(4) . . ?
C8 C3 C2 120.2(4) . . ?
C4 C3 C2 120.4(4) . . ?
C3 C4 C5 119.0(5) . . ?
C6 C5 C4 121.4(6) . . ?
C5 C6 C7 119.2(5) . . ?
C8 C7 C6 120.1(5) . . ?
C3 C8 C7 120.7(5) . . ?
C10 C9 C14 125.2(4) . . ?
C10 C9 N2 121.8(3) . . ?
C14 C9 N2 113.0(3) . . ?
C11 C10 C9 118.2(4) . . ?
C12 C11 C10 117.7(4) . . ?
C11 C12 C13 124.8(4) . . ?
C11 C12 F1 117.6(4) . . ?
C13 C12 F1 117.6(4) . . ?
C12 C13 C14 119.3(4) . . ?
C9 C14 C13 114.7(3) . . ?
C9 C14 Ir1 114.9(3) . . ?
C13 C14 Ir1 130.4(3) . . ?
N4 C15 C16 107.4(3) . . ?
N6 C16 C15 109.1(3) . . ?
N6 C16 C17 121.9(4) . . ?
C15 C16 C17 129.0(4) . . ?
C18 C17 C22 119.2(4) . . ?
C18 C17 C16 120.3(4) . . ?
C22 C17 C16 120.4(4) . . ?
C19 C18 C17 120.5(5) . . ?
C18 C19 C20 120.1(5) . . ?
C21 C20 C19 119.7(5) . . ?
C20 C21 C22 120.9(5) . . ?
C21 C22 C17 119.5(5) . . ?
C24 C23 C28 125.3(4) . . ?
C24 C23 N5 121.8(3) . . ?
C28 C23 N5 112.9(3) . . ?
C23 C24 C25 118.6(4) . . ?
C26 C25 C24 117.5(4) . . ?
C27 C26 F2 118.8(4) . . ?
C27 C26 C25 124.0(4) . . ?
F2 C26 C25 117.3(4) . . ?
C26 C27 C28 120.9(4) . . ?
C23 C28 C27 113.7(4) . . ?
C23 C28 Ir1 114.8(3) . . ?
C27 C28 Ir1 131.5(3) . . ?
O1 C29 N7 128.0(4) . . ?
O1 C29 C30 119.9(4) . . ?
N7 C29 C30 112.1(4) . . ?
N8 C30 C31 121.0(4) . . ?
N8 C30 C29 116.8(3) . . ?
C31 C30 C29 122.3(4) . . ?
C32 C31 C30 120.1(4) . . ?
C33 C32 C31 119.0(4) . . ?
C32 C33 C34 119.0(4) . . ?
N8 C34 C33 122.7(4) . . ?
N9 C35 C36 107.4(3) . . ?
N11 C36 C35 109.2(3) . . ?
N11 C36 C37 121.5(4) . . ?
C35 C36 C37 129.3(4) . . ?
C38 C37 C42 119.3(4) . . ?
C38 C37 C36 119.7(4) . . ?
C42 C37 C36 121.0(4) . . ?
C39 C38 C37 120.2(5) . . ?
C40 C39 C38 120.0(5) . . ?
C41 C40 C39 119.9(4) . . ?
C40 C41 C42 121.1(5) . . ?
C41 C42 C37 119.4(4) . . ?
C44 C43 C48 125.7(4) . . ?
C44 C43 N10 121.8(4) . . ?
C48 C43 N10 112.5(3) . . ?
C43 C44 C45 118.2(4) . . ?
C46 C45 C44 117.2(4) . . ?
C47 C46 F3 119.2(4) . . ?
C47 C46 C45 123.9(4) . . ?
F3 C46 C45 116.8(4) . . ?
C46 C47 C48 121.1(4) . . ?
C43 C48 C47 113.8(4) . . ?
C43 C48 Ir2 114.9(3) . . ?
C47 C48 Ir2 131.3(3) . . ?
N12 C49 C50 107.3(4) . . ?
N14 C50 C49 108.1(3) . . ?
N14 C50 C51 119.2(4) . . ?
C49 C50 C51 132.7(4) . . ?
C56 C51 C52 119.5(4) . . ?
C56 C51 C50 120.3(4) . . ?
C52 C51 C50 120.2(4) . . ?
C51 C52 C53 118.5(5) . . ?
C54 C53 C52 122.0(6) . . ?
C53 C54 C55 119.0(5) . . ?
C56 C55 C54 120.4(5) . . ?
C55 C56 C51 120.5(5) . . ?
C58 C57 C62 125.9(4) . . ?
C58 C57 N13 121.5(4) . . ?
C62 C57 N13 112.5(3) . . ?
C57 C58 C59 118.1(4) . . ?
C60 C59 C58 117.2(4) . . ?
C59 C60 C61 124.9(4) . . ?
C59 C60 F4 117.2(4) . . ?
C61 C60 F4 117.9(4) . . ?
C60 C61 C62 120.2(4) . . ?
C57 C62 C61 113.6(4) . . ?
C57 C62 Ir2 115.3(3) . . ?
C61 C62 Ir2 131.0(3) . . ?
O2 C63 N15 128.6(4) . . ?
O2 C63 C64 119.7(4) . . ?
N15 C63 C64 111.8(3) . . ?
N16 C64 C65 121.5(4) . . ?
N16 C64 C63 116.4(3) . . ?
C65 C64 C63 122.1(4) . . ?
C66 C65 C64 120.1(4) . . ?
C67 C66 C65 119.3(4) . . ?
C66 C67 C68 118.9(4) . . ?
N16 C68 C67 122.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         1.446
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.108
