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

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

data_aaa
_database_code_depnum_ccdc_archive 'CCDC 1046679'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C58 H44 F20 Ir2 N12 O P2'
_chemical_formula_sum            'C58 H44 F20 Ir2 N12 O P2'
_chemical_formula_weight         1751.39

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           triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   9.3820(19)
_cell_length_b                   13.771(3)
_cell_length_c                   14.966(3)
_cell_angle_alpha                63.00(3)
_cell_angle_beta                 76.75(3)
_cell_angle_gamma                82.82(3)
_cell_volume                     1676.5(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    4.116
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7357
_exptl_absorpt_correction_T_max  0.7518
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            11745
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         27.60
_reflns_number_total             7727
_reflns_number_gt                6034
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0938P)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         7727
_refine_ls_number_parameters     406
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      1.006
_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
Ir1 Ir 0.88654(3) 0.59825(2) 0.74044(2) 0.03654(12) Uani 1 1 d . . .
P1 P 1.6196(3) 0.8499(2) 0.3479(2) 0.0627(7) Uani 1 1 d . . .
F1 F 0.4712(7) 0.7587(5) 0.9402(4) 0.0829(18) Uani 1 1 d . . .
F2 F 0.6606(7) 0.4205(5) 1.1480(4) 0.0764(16) Uani 1 1 d . . .
F3 F 0.7391(8) 0.2189(5) 0.7978(6) 0.100(2) Uani 1 1 d U . .
F4 F 0.4189(6) 0.5046(5) 0.6422(5) 0.0768(17) Uani 1 1 d . . .
F5 F 1.6747(9) 0.7950(7) 0.2756(7) 0.114(3) Uani 1 1 d U . .
F6 F 1.5964(9) 0.7349(6) 0.4407(7) 0.123(3) Uani 1 1 d U . .
F7 F 1.6530(10) 0.9709(6) 0.2556(6) 0.114(3) Uani 1 1 d U . .
F8 F 1.5636(9) 0.9059(6) 0.4239(6) 0.108(2) Uani 1 1 d U . .
F9 F 1.4535(9) 0.8528(7) 0.3412(8) 0.125(3) Uani 1 1 d U . .
F10 F 1.7832(7) 0.8489(7) 0.3618(6) 0.110(2) Uani 1 1 d U . .
N1 N 1.0377(6) 0.6181(5) 0.6030(5) 0.0404(14) Uani 1 1 d . . .
N2 N 1.0540(7) 0.6961(6) 0.7309(6) 0.0501(17) Uani 1 1 d . . .
N3 N 0.6721(7) 0.7578(5) 0.7665(5) 0.0457(15) Uani 1 1 d . . .
N4 N 0.7655(7) 0.7354(5) 0.6921(5) 0.0441(15) Uani 1 1 d . . .
N5 N 0.9084(8) 0.3649(5) 0.8127(6) 0.0575(19) Uani 1 1 d . . .
N6 N 0.9836(8) 0.4495(6) 0.8060(6) 0.0515(17) Uani 1 1 d . . .
C1 C 1.0233(8) 0.5593(6) 0.5471(6) 0.0400(16) Uani 1 1 d . . .
C2 C 0.9077(8) 0.5886(6) 0.4955(6) 0.0472(18) Uani 1 1 d . . .
H2 H 0.8465 0.6481 0.4929 0.057 Uiso 1 1 calc R . .
C3 C 1.1142(9) 0.4721(7) 0.5515(6) 0.0498(19) Uani 1 1 d . . .
H3 H 1.1910 0.4540 0.5864 0.060 Uiso 1 1 calc R . .
C4 C 1.1505(8) 0.6693(6) 0.5855(7) 0.0476(19) Uani 1 1 d . . .
H4 H 1.2263 0.6746 0.5312 0.057 Uiso 1 1 calc R . .
C5 C 1.1630(9) 0.7195(6) 0.6485(7) 0.051(2) Uani 1 1 d . . .
C6 C 1.2712(9) 0.7923(7) 0.6256(9) 0.062(2) Uani 1 1 d . . .
H6 H 1.3477 0.8059 0.5697 0.075 Uiso 1 1 calc R . .
C7 C 1.2636(12) 0.8434(9) 0.6858(11) 0.081(3) Uani 1 1 d . . .
H7 H 1.3313 0.8960 0.6683 0.097 Uiso 1 1 calc R . .
C8 C 1.1561(11) 0.8176(10) 0.7727(12) 0.086(4) Uani 1 1 d . . .
H8 H 1.1536 0.8491 0.8165 0.103 Uiso 1 1 calc R . .
C9 C 1.0517(10) 0.7432(8) 0.7930(9) 0.068(3) Uani 1 1 d . . .
H9 H 0.9781 0.7254 0.8510 0.082 Uiso 1 1 calc R . .
C10 C 0.6108(9) 0.8578(7) 0.7233(7) 0.054(2) Uani 1 1 d . . .
H10 H 0.5464 0.8917 0.7585 0.065 Uiso 1 1 calc R . .
C11 C 0.6570(11) 0.9008(8) 0.6221(8) 0.062(2) Uani 1 1 d . . .
H11 H 0.6296 0.9680 0.5737 0.074 Uiso 1 1 calc R . .
C12 C 0.7553(10) 0.8238(7) 0.6042(7) 0.055(2) Uani 1 1 d . . .
H12 H 0.8066 0.8326 0.5400 0.066 Uiso 1 1 calc R . .
C13 C 0.6642(8) 0.6731(6) 0.8655(6) 0.0394(16) Uani 1 1 d . . .
C14 C 0.5685(9) 0.6736(7) 0.9512(7) 0.051(2) Uani 1 1 d . . .
C15 C 0.5675(9) 0.5901(7) 1.0453(7) 0.054(2) Uani 1 1 d . . .
H15 H 0.5044 0.5917 1.1025 0.064 Uiso 1 1 calc R . .
C16 C 0.6609(9) 0.5038(7) 1.0543(7) 0.052(2) Uani 1 1 d . . .
C17 C 0.7569(9) 0.4979(6) 0.9718(7) 0.0469(19) Uani 1 1 d . . .
H17 H 0.8186 0.4371 0.9810 0.056 Uiso 1 1 calc R . .
C18 C 0.7605(7) 0.5851(6) 0.8735(6) 0.0388(16) Uani 1 1 d . . .
C19 C 0.9800(14) 0.2696(9) 0.8592(11) 0.090(3) Uani 1 1 d U . .
H19 H 0.9538 0.2003 0.8736 0.108 Uiso 1 1 calc R . .
C20 C 1.1044(15) 0.2975(10) 0.8817(10) 0.094(4) Uani 1 1 d U . .
H20 H 1.1755 0.2497 0.9143 0.113 Uiso 1 1 calc R . .
C21 C 1.0988(10) 0.4056(8) 0.8469(9) 0.068(3) Uani 1 1 d . . .
H21 H 1.1684 0.4450 0.8513 0.082 Uiso 1 1 calc R . .
C22 C 0.7778(9) 0.3954(7) 0.7689(7) 0.0500(19) Uani 1 1 d . . .
C23 C 0.6994(11) 0.3258(8) 0.7620(9) 0.068(3) Uani 1 1 d . . .
C24 C 0.5747(13) 0.3599(9) 0.7194(9) 0.074(3) Uani 1 1 d . . .
H24 H 0.5189 0.3111 0.7156 0.089 Uiso 1 1 calc R . .
C25 C 0.5374(10) 0.4687(8) 0.6832(7) 0.057(2) Uani 1 1 d . . .
C26 C 0.6186(8) 0.5435(7) 0.6888(7) 0.0476(18) Uani 1 1 d . . .
H26 H 0.5892 0.6166 0.6644 0.057 Uiso 1 1 calc R . .
C27 C 0.7436(8) 0.5078(6) 0.7312(6) 0.0390(16) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N4 1.995(7) . ?
Ir1 C27 2.007(7) . ?
Ir1 C18 2.011(7) . ?
Ir1 N6 2.027(7) . ?
Ir1 N2 2.134(6) . ?
Ir1 N1 2.137(6) . ?
P1 F5 1.550(7) . ?
P1 F6 1.561(7) . ?
P1 F9 1.580(7) . ?
P1 F10 1.593(7) . ?
P1 F8 1.608(7) . ?
P1 F7 1.620(8) . ?
F1 C14 1.364(9) . ?
F2 C16 1.350(10) . ?
F3 C23 1.354(11) . ?
F4 C25 1.326(10) . ?
N1 C4 1.257(9) . ?
N1 C1 1.437(9) . ?
N2 C5 1.347(11) . ?
N2 C9 1.349(11) . ?
N3 C10 1.346(10) . ?
N3 N4 1.378(9) . ?
N3 C13 1.401(10) . ?
N4 C12 1.340(11) . ?
N5 C19 1.350(13) . ?
N5 N6 1.390(9) . ?
N5 C22 1.449(11) . ?
N6 C21 1.309(11) . ?
C1 C3 1.369(10) . ?
C1 C2 1.388(10) . ?
C2 C3 1.370(11) 2_766 ?
C2 H2 0.9300 . ?
C3 C2 1.370(11) 2_766 ?
C3 H3 0.9300 . ?
C4 C5 1.429(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(11) . ?
C6 C7 1.359(15) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(13) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.335(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.396(13) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.389(11) . ?
C13 C18 1.395(10) . ?
C14 C15 1.354(12) . ?
C15 C16 1.359(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(12) . ?
C17 C18 1.410(11) . ?
C17 H17 0.9300 . ?
C19 C20 1.425(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.334(15) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.330(12) . ?
C22 C27 1.409(11) . ?
C23 C24 1.389(15) . ?
C24 C25 1.371(14) . ?
C24 H24 0.9300 . ?
C25 C26 1.398(11) . ?
C26 C27 1.390(10) . ?
C26 H26 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
N4 Ir1 C27 94.6(3) . . ?
N4 Ir1 C18 79.2(3) . . ?
C27 Ir1 C18 89.1(3) . . ?
N4 Ir1 N6 171.6(3) . . ?
C27 Ir1 N6 81.0(3) . . ?
C18 Ir1 N6 93.5(3) . . ?
N4 Ir1 N2 86.6(3) . . ?
C27 Ir1 N2 172.4(3) . . ?
C18 Ir1 N2 98.5(3) . . ?
N6 Ir1 N2 98.8(3) . . ?
N4 Ir1 N1 101.7(2) . . ?
C27 Ir1 N1 96.6(3) . . ?
C18 Ir1 N1 174.1(2) . . ?
N6 Ir1 N1 85.9(3) . . ?
N2 Ir1 N1 75.8(3) . . ?
F5 P1 F6 89.5(5) . . ?
F5 P1 F9 94.3(5) . . ?
F6 P1 F9 88.8(5) . . ?
F5 P1 F10 89.7(5) . . ?
F6 P1 F10 90.2(4) . . ?
F9 P1 F10 175.8(5) . . ?
F5 P1 F8 179.3(5) . . ?
F6 P1 F8 90.0(5) . . ?
F9 P1 F8 86.1(5) . . ?
F10 P1 F8 89.8(5) . . ?
F5 P1 F7 92.5(4) . . ?
F6 P1 F7 175.6(5) . . ?
F9 P1 F7 94.9(5) . . ?
F10 P1 F7 85.9(5) . . ?
F8 P1 F7 87.9(4) . . ?
C4 N1 C1 122.9(7) . . ?
C4 N1 Ir1 114.6(6) . . ?
C1 N1 Ir1 121.5(5) . . ?
C5 N2 C9 119.0(7) . . ?
C5 N2 Ir1 114.7(5) . . ?
C9 N2 Ir1 126.0(6) . . ?
C10 N3 N4 109.7(7) . . ?
C10 N3 C13 136.4(7) . . ?
N4 N3 C13 113.9(6) . . ?
C12 N4 N3 104.8(7) . . ?
C12 N4 Ir1 138.3(6) . . ?
N3 N4 Ir1 116.6(5) . . ?
C19 N5 N6 109.2(7) . . ?
C19 N5 C22 134.4(8) . . ?
N6 N5 C22 116.4(6) . . ?
C21 N6 N5 106.9(7) . . ?
C21 N6 Ir1 139.2(6) . . ?
N5 N6 Ir1 113.9(5) . . ?
C3 C1 C2 121.3(7) . . ?
C3 C1 N1 120.7(7) . . ?
C2 C1 N1 117.8(6) . . ?
C3 C2 C1 118.5(7) 2_766 . ?
C3 C2 H2 120.8 2_766 . ?
C1 C2 H2 120.8 . . ?
C1 C3 C2 120.2(7) . 2_766 ?
C1 C3 H3 119.9 . . ?
C2 C3 H3 119.9 2_766 . ?
N1 C4 C5 120.4(8) . . ?
N1 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N2 C5 C6 121.3(8) . . ?
N2 C5 C4 114.1(7) . . ?
C6 C5 C4 124.4(8) . . ?
C7 C6 C5 119.1(10) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 120.5(9) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 118.0(10) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
N2 C9 C8 121.9(10) . . ?
N2 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C11 C10 N3 109.2(8) . . ?
C11 C10 H10 125.4 . . ?
N3 C10 H10 125.4 . . ?
C10 C11 C12 105.5(8) . . ?
C10 C11 H11 127.2 . . ?
C12 C11 H11 127.2 . . ?
N4 C12 C11 110.7(9) . . ?
N4 C12 H12 124.6 . . ?
C11 C12 H12 124.6 . . ?
C14 C13 C18 120.8(7) . . ?
C14 C13 N3 124.0(7) . . ?
C18 C13 N3 115.1(7) . . ?
C15 C14 F1 119.2(8) . . ?
C15 C14 C13 121.3(8) . . ?
F1 C14 C13 119.5(8) . . ?
C14 C15 C16 118.4(8) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
F2 C16 C15 118.6(8) . . ?
F2 C16 C17 118.5(8) . . ?
C15 C16 C17 122.9(8) . . ?
C16 C17 C18 119.3(7) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C13 C18 C17 117.2(7) . . ?
C13 C18 Ir1 114.8(6) . . ?
C17 C18 Ir1 128.0(6) . . ?
N5 C19 C20 105.5(9) . . ?
N5 C19 H19 127.3 . . ?
C20 C19 H19 127.3 . . ?
C21 C20 C19 106.6(9) . . ?
C21 C20 H20 126.7 . . ?
C19 C20 H20 126.7 . . ?
N6 C21 C20 111.8(9) . . ?
N6 C21 H21 124.1 . . ?
C20 C21 H21 124.1 . . ?
C23 C22 C27 122.9(8) . . ?
C23 C22 N5 124.1(8) . . ?
C27 C22 N5 113.0(7) . . ?
C22 C23 F3 120.3(9) . . ?
C22 C23 C24 121.4(9) . . ?
F3 C23 C24 118.2(8) . . ?
C25 C24 C23 117.0(8) . . ?
C25 C24 H24 121.5 . . ?
C23 C24 H24 121.5 . . ?
F4 C25 C24 119.0(8) . . ?
F4 C25 C26 118.4(8) . . ?
C24 C25 C26 122.6(8) . . ?
C27 C26 C25 119.5(8) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C22 116.5(7) . . ?
C26 C27 Ir1 127.8(6) . . ?
C22 C27 Ir1 115.7(6) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         2.368
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.189
