# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_007c-18031
_database_code_depnum_ccdc_archive 'CCDC 2001541'
loop_
_audit_author_name
_audit_author_address
'Brandon Mercado'
;Yale University
United States of America
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;

_vrf_DIFMN02_007c-18031          
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: The crystal was a twin, which resulted in spurious difference
map peaks. Accounting for the twin did not completely eliminate all oddly placed
difference map peaks. The remaining peaks are near the special positions
and heavy metal center. Fourier artifacts may also be contributing to these 
peaks. 
;

_vrf_PLAT098_007c-18031          
;
PROBLEM: Large Reported Min.  (Negative) Residual Density 
RESPONSE: See response to DIFMN02
;

_vrf_PLAT213_007c-18031          
;
PROBLEM: Atom X              has ADP max/min Ratio
RESPONSE: The data was twinned and not the best quality.
The ADPs near the metal center are extremely small. See response to DIFMN02
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H41 F6 Ir N3 O P3'
_chemical_formula_sum            'C22 H41 F6 Ir N3 O P3'
_chemical_formula_weight         762.69

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'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   11.5628(2)
_cell_length_b                   11.2503(2)
_cell_length_c                   22.9994(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.550(2)
_cell_angle_gamma                90
_cell_volume                     2986.14(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    38245
_cell_measurement_theta_min      3.1190
_cell_measurement_theta_max      27.5300

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_F_000             1512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.690
_shelx_estimated_absorpt_T_min   0.651
_shelx_estimated_absorpt_T_max   0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Dectris Pilatus 3R'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8
_diffrn_reflns_number            3424
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.026
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3424
_reflns_number_gt                3388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 This data was refined as a 2-component twin. The fractional volume contribution of the minor twin component
 was freely refined to a converged value of 0.239(3).
 
 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 hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+102.4701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3424
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.5000 0.38631(3) 0.7500 0.00904(12) Uani 1 2 d S T P . .
P1 P 0.50983(16) 0.35947(15) 0.65192(7) 0.0111(3) Uani 1 1 d . . . . .
P2 P 0.5000 0.0000 0.5000 0.0151(5) Uani 1 2 d S . P . .
F1 F 0.3974(5) 0.0460(5) 0.5376(3) 0.0371(13) Uani 1 1 d . . . . .
F2 F 0.4919(5) 0.1196(4) 0.4624(2) 0.0316(12) Uani 1 1 d . . . . .
F3 F 0.4081(5) -0.0632(5) 0.4550(2) 0.0341(12) Uani 1 1 d . . . . .
O1 O 0.5000 0.6520(7) 0.7500 0.043(3) Uani 1 2 d S T P . .
N1 N 0.5000 0.2018(7) 0.7500 0.0122(16) Uani 1 2 d S T P . .
N2 N 0.4996(6) 0.2080(5) 0.6488(3) 0.0137(12) Uani 1 1 d . . . . .
H2 H 0.506(7) 0.174(8) 0.619(4) 0.01(2) Uiso 1 1 d . . . . .
C1 C 0.5000 0.5483(9) 0.7500 0.021(2) Uani 1 2 d S T P . .
C2 C 0.5008(6) 0.1403(6) 0.6986(3) 0.0109(12) Uani 1 1 d . . . . .
C3 C 0.5016(6) 0.0169(6) 0.6978(3) 0.0147(11) Uani 1 1 d . . . . .
H3 H 0.5032 -0.0245 0.6618 0.018 Uiso 1 1 calc R U . . .
C4 C 0.5000 -0.0460(8) 0.7500 0.0147(11) Uani 1 2 d S T P . .
H4 H 0.5000 -0.1304 0.7500 0.018 Uiso 1 2 calc R U P . .
C5 C 0.6557(7) 0.3921(7) 0.6243(3) 0.0196(15) Uani 1 1 d . . . . .
C6 C 0.7420(8) 0.3132(8) 0.6607(4) 0.0288(18) Uani 1 1 d . . . . .
H6A H 0.7378 0.3320 0.7021 0.043 Uiso 1 1 calc R U . . .
H6B H 0.8208 0.3281 0.6490 0.043 Uiso 1 1 calc R U . . .
H6C H 0.7223 0.2293 0.6540 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6869(8) 0.5231(7) 0.6364(4) 0.0251(17) Uani 1 1 d . . . . .
H7A H 0.6285 0.5745 0.6166 0.038 Uiso 1 1 calc R U . . .
H7B H 0.7631 0.5403 0.6220 0.038 Uiso 1 1 calc R U . . .
H7C H 0.6890 0.5380 0.6785 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6633(8) 0.3643(8) 0.5591(4) 0.0267(17) Uani 1 1 d . . . . .
H8A H 0.6379 0.2824 0.5514 0.040 Uiso 1 1 calc R U . . .
H8B H 0.7435 0.3737 0.5484 0.040 Uiso 1 1 calc R U . . .
H8C H 0.6132 0.4191 0.5360 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3847(7) 0.4109(7) 0.6044(3) 0.0188(15) Uani 1 1 d . . . . .
C10 C 0.3934(8) 0.5457(7) 0.5955(4) 0.0234(17) Uani 1 1 d . . . . .
H10A H 0.4072 0.5848 0.6334 0.035 Uiso 1 1 calc R U . . .
H10B H 0.3209 0.5752 0.5764 0.035 Uiso 1 1 calc R U . . .
H10C H 0.4577 0.5632 0.5710 0.035 Uiso 1 1 calc R U . . .
C11 C 0.2770(7) 0.3826(9) 0.6384(4) 0.0292(19) Uani 1 1 d . . . . .
H11A H 0.2785 0.2987 0.6500 0.044 Uiso 1 1 calc R U . . .
H11B H 0.2067 0.3984 0.6136 0.044 Uiso 1 1 calc R U . . .
H11C H 0.2773 0.4327 0.6733 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3699(8) 0.3470(8) 0.5455(4) 0.0253(17) Uani 1 1 d . . . . .
H12A H 0.4378 0.3622 0.5231 0.038 Uiso 1 1 calc R U . . .
H12B H 0.3002 0.3767 0.5238 0.038 Uiso 1 1 calc R U . . .
H12C H 0.3623 0.2613 0.5519 0.038 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C1 1.822(10) . ?
Ir1 N1 2.076(8) . ?
Ir1 P1 2.2857(17) . ?
Ir1 P1 2.2858(17) 2_656 ?
P1 N2 1.710(6) . ?
P1 C9 1.850(8) . ?
P1 C5 1.875(8) . ?
P2 F1 1.597(5) . ?
P2 F1 1.597(5) 5_656 ?
P2 F2 1.599(5) . ?
P2 F2 1.599(5) 5_656 ?
P2 F3 1.604(5) . ?
P2 F3 1.604(5) 5_656 ?
O1 C1 1.166(14) . ?
N1 C2 1.371(8) 2_656 ?
N1 C2 1.371(8) . ?
N2 C2 1.374(9) . ?
N2 H2 0.79(9) . ?
C2 C3 1.388(9) . ?
C3 C4 1.395(9) . ?
C3 H3 0.9500 . ?
C4 C3 1.395(9) 2_656 ?
C4 H4 0.9500 . ?
C5 C7 1.539(11) . ?
C5 C8 1.540(11) . ?
C5 C6 1.543(12) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C12 1.534(11) . ?
C9 C10 1.535(11) . ?
C9 C11 1.545(12) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 N1 180.0 . . ?
C1 Ir1 P1 97.59(4) . . ?
N1 Ir1 P1 82.41(4) . . ?
C1 Ir1 P1 97.59(4) . 2_656 ?
N1 Ir1 P1 82.41(4) . 2_656 ?
P1 Ir1 P1 164.82(9) . 2_656 ?
N2 P1 C9 103.7(3) . . ?
N2 P1 C5 104.0(3) . . ?
C9 P1 C5 115.2(4) . . ?
N2 P1 Ir1 99.5(2) . . ?
C9 P1 Ir1 117.2(3) . . ?
C5 P1 Ir1 114.1(3) . . ?
F1 P2 F1 180.0 . 5_656 ?
F1 P2 F2 90.0(3) . . ?
F1 P2 F2 90.0(3) 5_656 . ?
F1 P2 F2 90.0(3) . 5_656 ?
F1 P2 F2 90.0(3) 5_656 5_656 ?
F2 P2 F2 180.0 . 5_656 ?
F1 P2 F3 90.5(3) . . ?
F1 P2 F3 89.5(3) 5_656 . ?
F2 P2 F3 90.6(3) . . ?
F2 P2 F3 89.4(3) 5_656 . ?
F1 P2 F3 89.5(3) . 5_656 ?
F1 P2 F3 90.5(3) 5_656 5_656 ?
F2 P2 F3 89.4(3) . 5_656 ?
F2 P2 F3 90.6(3) 5_656 5_656 ?
F3 P2 F3 180.0 . 5_656 ?
C2 N1 C2 119.4(8) 2_656 . ?
C2 N1 Ir1 120.3(4) 2_656 . ?
C2 N1 Ir1 120.3(4) . . ?
C2 N2 P1 121.4(5) . . ?
C2 N2 H2 117(6) . . ?
P1 N2 H2 121(6) . . ?
O1 C1 Ir1 180.0 . . ?
N1 C2 N2 116.0(6) . . ?
N1 C2 C3 121.1(6) . . ?
N2 C2 C3 122.9(6) . . ?
C2 C3 C4 119.7(7) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C3 119.1(8) . 2_656 ?
C3 C4 H4 120.5 . . ?
C3 C4 H4 120.5 2_656 . ?
C7 C5 C8 110.1(7) . . ?
C7 C5 C6 108.4(7) . . ?
C8 C5 C6 109.7(7) . . ?
C7 C5 P1 109.4(5) . . ?
C8 C5 P1 113.4(6) . . ?
C6 C5 P1 105.6(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C9 C10 110.4(7) . . ?
C12 C9 C11 107.5(7) . . ?
C10 C9 C11 109.4(7) . . ?
C12 C9 P1 114.6(5) . . ?
C10 C9 P1 109.4(5) . . ?
C11 C9 P1 105.2(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C9 P1 N2 C2 -127.8(6) . . . . ?
C5 P1 N2 C2 111.3(6) . . . . ?
Ir1 P1 N2 C2 -6.7(6) . . . . ?
C2 N1 C2 N2 178.9(7) 2_656 . . . ?
Ir1 N1 C2 N2 -1.1(7) . . . . ?
C2 N1 C2 C3 -0.4(5) 2_656 . . . ?
Ir1 N1 C2 C3 179.6(5) . . . . ?
P1 N2 C2 N1 5.8(8) . . . . ?
P1 N2 C2 C3 -174.9(6) . . . . ?
N1 C2 C3 C4 0.9(10) . . . . ?
N2 C2 C3 C4 -178.4(6) . . . . ?
C2 C3 C4 C3 -0.4(5) . . . 2_656 ?
N2 P1 C5 C7 -168.5(6) . . . . ?
C9 P1 C5 C7 78.7(6) . . . . ?
Ir1 P1 C5 C7 -61.1(6) . . . . ?
N2 P1 C5 C8 68.2(6) . . . . ?
C9 P1 C5 C8 -44.7(7) . . . . ?
Ir1 P1 C5 C8 175.5(5) . . . . ?
N2 P1 C5 C6 -52.0(6) . . . . ?
C9 P1 C5 C6 -164.8(5) . . . . ?
Ir1 P1 C5 C6 55.4(6) . . . . ?
N2 P1 C9 C12 -46.7(7) . . . . ?
C5 P1 C9 C12 66.3(7) . . . . ?
Ir1 P1 C9 C12 -155.2(5) . . . . ?
N2 P1 C9 C10 -171.3(5) . . . . ?
C5 P1 C9 C10 -58.3(6) . . . . ?
Ir1 P1 C9 C10 80.2(6) . . . . ?
N2 P1 C9 C11 71.2(6) . . . . ?
C5 P1 C9 C11 -175.8(5) . . . . ?
Ir1 P1 C9 C11 -37.3(6) . . . . ?

_refine_diff_density_max         3.268
_refine_diff_density_min         -9.314
_refine_diff_density_rms         0.250



####################################################################### 
# 
# 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_007c-18033
_database_code_depnum_ccdc_archive 'CCDC 2001542'
loop_
_audit_author_name
_audit_author_address
'Brandon Mercado'
;Yale University
United States of America
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H39 Ir N O3 P2, F6 P'
_chemical_formula_sum            'C22 H39 F6 Ir N O3 P3'
_chemical_formula_weight         764.65

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.4834(2)
_cell_length_b                   27.8076(7)
_cell_length_c                   12.4613(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.593(2)
_cell_angle_gamma                90
_cell_volume                     2938.52(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    32091
_cell_measurement_theta_min      3.0180
_cell_measurement_theta_max      28.1040

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_F_000             1512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    4.769
_shelx_estimated_absorpt_T_min   0.311
_shelx_estimated_absorpt_T_max   0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Dectris Pilatus 3R'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8
_diffrn_reflns_number            76580
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6716
_reflns_number_gt                6332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_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 hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²+7.4712P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6716
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.33900(2) 0.60802(2) 0.40343(2) 0.01681(5) Uani 1 1 d . . . . .
P1 P 0.38447(10) 0.65829(3) 0.54596(7) 0.01980(16) Uani 1 1 d . . . . .
P2 P 0.22794(10) 0.57507(3) 0.25090(6) 0.01931(16) Uani 1 1 d . . . . .
O1 O 0.5998(3) 0.53701(10) 0.4441(2) 0.0369(6) Uani 1 1 d . . . . .
O2 O 0.2518(3) 0.70196(9) 0.52065(19) 0.0262(5) Uani 1 1 d . . . . .
O3 O 0.0939(3) 0.61699(9) 0.21652(19) 0.0261(5) Uani 1 1 d . . . . .
N1 N 0.1736(3) 0.65997(9) 0.3677(2) 0.0184(5) Uani 1 1 d . . . . .
C1 C 0.4960(4) 0.56350(12) 0.4300(3) 0.0237(7) Uani 1 1 d . . . . .
C2 C 0.1605(4) 0.69987(12) 0.4299(3) 0.0223(7) Uani 1 1 d . . . . .
C3 C 0.0601(4) 0.73733(13) 0.4043(3) 0.0275(7) Uani 1 1 d . . . . .
H3 H 0.0530 0.7648 0.4494 0.033 Uiso 1 1 calc R U . . .
C4 C -0.0305(4) 0.73341(13) 0.3100(3) 0.0302(8) Uani 1 1 d . . . . .
H4 H -0.0996 0.7589 0.2897 0.036 Uiso 1 1 calc R U . . .
C5 C -0.0221(4) 0.69312(14) 0.2450(3) 0.0291(8) Uani 1 1 d . . . . .
H5 H -0.0848 0.6904 0.1809 0.035 Uiso 1 1 calc R U . . .
C6 C 0.0812(4) 0.65694(12) 0.2769(3) 0.0225(7) Uani 1 1 d . . . . .
C7 C 0.3198(4) 0.63595(13) 0.6776(3) 0.0253(7) Uani 1 1 d . . . . .
C8 C 0.1463(5) 0.62098(19) 0.6597(4) 0.0449(11) Uani 1 1 d . . . . .
H8A H 0.0824 0.6495 0.6430 0.067 Uiso 1 1 calc R U . . .
H8B H 0.1082 0.6057 0.7249 0.067 Uiso 1 1 calc R U . . .
H8C H 0.1380 0.5982 0.5997 0.067 Uiso 1 1 calc R U . . .
C9 C 0.4179(6) 0.59098(15) 0.7063(3) 0.0378(9) Uani 1 1 d . . . . .
H9A H 0.4050 0.5671 0.6489 0.057 Uiso 1 1 calc R U . . .
H9B H 0.3818 0.5774 0.7738 0.057 Uiso 1 1 calc R U . . .
H9C H 0.5294 0.5998 0.7143 0.057 Uiso 1 1 calc R U . . .
C10 C 0.3318(6) 0.67274(16) 0.7692(3) 0.0419(10) Uani 1 1 d . . . . .
H10A H 0.4430 0.6788 0.7878 0.063 Uiso 1 1 calc R U . . .
H10B H 0.2786 0.6601 0.8321 0.063 Uiso 1 1 calc R U . . .
H10C H 0.2813 0.7029 0.7462 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5676(5) 0.69466(14) 0.5466(3) 0.0317(8) Uani 1 1 d . . . . .
C12 C 0.5791(6) 0.71298(17) 0.4308(4) 0.0440(11) Uani 1 1 d . . . . .
H12A H 0.5821 0.6855 0.3816 0.066 Uiso 1 1 calc R U . . .
H12B H 0.6754 0.7321 0.4242 0.066 Uiso 1 1 calc R U . . .
H12C H 0.4871 0.7330 0.4127 0.066 Uiso 1 1 calc R U . . .
C13 C 0.7088(5) 0.6621(2) 0.5727(5) 0.0574(14) Uani 1 1 d . . . . .
H13A H 0.7048 0.6515 0.6476 0.086 Uiso 1 1 calc R U . . .
H13B H 0.8068 0.6800 0.5622 0.086 Uiso 1 1 calc R U . . .
H13C H 0.7055 0.6340 0.5252 0.086 Uiso 1 1 calc R U . . .
C14 C 0.5648(6) 0.73826(18) 0.6226(4) 0.0531(13) Uani 1 1 d . . . . .
H14A H 0.4634 0.7549 0.6140 0.080 Uiso 1 1 calc R U . . .
H14B H 0.6503 0.7604 0.6051 0.080 Uiso 1 1 calc R U . . .
H14C H 0.5789 0.7273 0.6970 0.080 Uiso 1 1 calc R U . . .
C15 C 0.0967(4) 0.52289(13) 0.2699(3) 0.0280(7) Uani 1 1 d . . . . .
C16 C 0.2012(6) 0.47848(15) 0.2892(4) 0.0486(12) Uani 1 1 d . . . . .
H16A H 0.2566 0.4708 0.2234 0.073 Uiso 1 1 calc R U . . .
H16B H 0.1354 0.4511 0.3092 0.073 Uiso 1 1 calc R U . . .
H16C H 0.2784 0.4852 0.3473 0.073 Uiso 1 1 calc R U . . .
C17 C 0.0044(6) 0.53420(19) 0.3705(4) 0.0528(13) Uani 1 1 d . . . . .
H17A H 0.0782 0.5391 0.4315 0.079 Uiso 1 1 calc R U . . .
H17B H -0.0660 0.5073 0.3860 0.079 Uiso 1 1 calc R U . . .
H17C H -0.0581 0.5634 0.3586 0.079 Uiso 1 1 calc R U . . .
C18 C -0.0216(5) 0.51403(16) 0.1766(4) 0.0421(10) Uani 1 1 d . . . . .
H18A H -0.0767 0.5441 0.1587 0.063 Uiso 1 1 calc R U . . .
H18B H -0.0984 0.4897 0.1977 0.063 Uiso 1 1 calc R U . . .
H18C H 0.0347 0.5026 0.1139 0.063 Uiso 1 1 calc R U . . .
C19 C 0.3503(5) 0.57440(14) 0.1300(3) 0.0301(8) Uani 1 1 d . . . . .
C20 C 0.2675(6) 0.55431(18) 0.0290(3) 0.0456(11) Uani 1 1 d . . . . .
H20A H 0.2518 0.5196 0.0373 0.068 Uiso 1 1 calc R U . . .
H20B H 0.3326 0.5603 -0.0333 0.068 Uiso 1 1 calc R U . . .
H20C H 0.1650 0.5701 0.0183 0.068 Uiso 1 1 calc R U . . .
C21 C 0.5008(5) 0.5463(2) 0.1541(4) 0.0475(11) Uani 1 1 d . . . . .
H21A H 0.5565 0.5604 0.2164 0.071 Uiso 1 1 calc R U . . .
H21B H 0.5686 0.5475 0.0918 0.071 Uiso 1 1 calc R U . . .
H21C H 0.4743 0.5127 0.1698 0.071 Uiso 1 1 calc R U . . .
C22 C 0.3884(6) 0.62797(17) 0.1084(4) 0.0497(12) Uani 1 1 d . . . . .
H22A H 0.2914 0.6449 0.0866 0.075 Uiso 1 1 calc R U . . .
H22B H 0.4646 0.6302 0.0510 0.075 Uiso 1 1 calc R U . . .
H22C H 0.4331 0.6426 0.1739 0.075 Uiso 1 1 calc R U . . .
P3 P 0.82249(13) 0.86633(3) 0.44206(8) 0.0311(2) Uani 1 1 d . . . . .
F1 F 0.8965(6) 0.91809(13) 0.4395(5) 0.124(2) Uani 1 1 d . . . . .
F2 F 0.6550(4) 0.88761(12) 0.4076(2) 0.0624(9) Uani 1 1 d . . . . .
F3 F 0.8611(5) 0.8563(2) 0.3229(3) 0.1073(17) Uani 1 1 d . . . . .
F4 F 0.9955(3) 0.84627(10) 0.4789(3) 0.0597(8) Uani 1 1 d . . . . .
F5 F 0.7872(5) 0.87597(17) 0.5643(2) 0.0954(15) Uani 1 1 d . . . . .
F6 F 0.7594(5) 0.81492(13) 0.4552(5) 0.1145(17) 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 C1 1.841(3) . ?
Ir1 N1 2.054(3) . ?
Ir1 P1 2.2846(8) . ?
Ir1 P2 2.2892(8) . ?
P1 O2 1.680(3) . ?
P1 C7 1.851(3) . ?
P1 C11 1.854(4) . ?
P2 O3 1.676(3) . ?
P2 C15 1.848(4) . ?
P2 C19 1.853(4) . ?
O1 C1 1.158(4) . ?
O2 C2 1.354(4) . ?
O3 C6 1.347(4) . ?
N1 C2 1.359(4) . ?
N1 C6 1.362(4) . ?
C2 C3 1.377(5) . ?
C3 C4 1.391(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9500 . ?
C7 C10 1.534(5) . ?
C7 C9 1.539(5) . ?
C7 C8 1.540(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.529(6) . ?
C11 C12 1.536(6) . ?
C11 C14 1.539(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.529(6) . ?
C15 C18 1.535(5) . ?
C15 C16 1.535(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.520(6) . ?
C19 C20 1.530(6) . ?
C19 C22 1.549(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
P3 F6 1.537(3) . ?
P3 F3 1.554(3) . ?
P3 F1 1.571(4) . ?
P3 F5 1.584(3) . ?
P3 F2 1.587(3) . ?
P3 F4 1.624(3) . ?

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 N1 176.37(13) . . ?
C1 Ir1 P1 99.55(11) . . ?
N1 Ir1 P1 80.66(8) . . ?
C1 Ir1 P2 99.15(11) . . ?
N1 Ir1 P2 80.72(8) . . ?
P1 Ir1 P2 161.28(3) . . ?
O2 P1 C7 101.27(15) . . ?
O2 P1 C11 99.41(16) . . ?
C7 P1 C11 116.63(17) . . ?
O2 P1 Ir1 101.45(9) . . ?
C7 P1 Ir1 115.83(12) . . ?
C11 P1 Ir1 117.43(13) . . ?
O3 P2 C15 99.90(16) . . ?
O3 P2 C19 100.99(16) . . ?
C15 P2 C19 116.71(18) . . ?
O3 P2 Ir1 101.22(9) . . ?
C15 P2 Ir1 116.30(12) . . ?
C19 P2 Ir1 116.88(13) . . ?
C2 O2 P1 119.4(2) . . ?
C6 O3 P2 119.7(2) . . ?
C2 N1 C6 118.0(3) . . ?
C2 N1 Ir1 121.1(2) . . ?
C6 N1 Ir1 120.7(2) . . ?
O1 C1 Ir1 176.6(3) . . ?
O2 C2 N1 117.2(3) . . ?
O2 C2 C3 119.7(3) . . ?
N1 C2 C3 123.1(3) . . ?
C2 C3 C4 117.4(3) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 117.5(3) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
O3 C6 N1 117.5(3) . . ?
O3 C6 C5 119.9(3) . . ?
N1 C6 C5 122.6(3) . . ?
C10 C7 C9 110.2(3) . . ?
C10 C7 C8 109.4(3) . . ?
C9 C7 C8 108.8(3) . . ?
C10 C7 P1 114.9(3) . . ?
C9 C7 P1 107.9(2) . . ?
C8 C7 P1 105.5(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C12 109.1(4) . . ?
C13 C11 C14 111.1(4) . . ?
C12 C11 C14 108.6(4) . . ?
C13 C11 P1 109.3(3) . . ?
C12 C11 P1 104.6(3) . . ?
C14 C11 P1 113.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C15 C18 108.4(4) . . ?
C17 C15 C16 110.1(4) . . ?
C18 C15 C16 110.6(3) . . ?
C17 C15 P2 105.5(3) . . ?
C18 C15 P2 114.3(3) . . ?
C16 C15 P2 107.7(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 C20 109.8(3) . . ?
C21 C19 C22 110.6(4) . . ?
C20 C19 C22 107.5(4) . . ?
C21 C19 P2 109.3(3) . . ?
C20 C19 P2 114.7(3) . . ?
C22 C19 P2 104.8(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F6 P3 F3 91.0(3) . . ?
F6 P3 F1 174.3(3) . . ?
F3 P3 F1 92.9(3) . . ?
F6 P3 F5 88.8(3) . . ?
F3 P3 F5 178.6(2) . . ?
F1 P3 F5 87.2(3) . . ?
F6 P3 F2 93.7(2) . . ?
F3 P3 F2 91.1(2) . . ?
F1 P3 F2 90.5(2) . . ?
F5 P3 F2 90.32(17) . . ?
F6 P3 F4 88.0(2) . . ?
F3 P3 F4 89.7(2) . . ?
F1 P3 F4 87.8(2) . . ?
F5 P3 F4 88.86(18) . . ?
F2 P3 F4 178.14(18) . . ?

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
C7 P1 O2 C2 -122.0(3) . . . . ?
C11 P1 O2 C2 118.2(3) . . . . ?
Ir1 P1 O2 C2 -2.4(3) . . . . ?
C15 P2 O3 C6 120.4(3) . . . . ?
C19 P2 O3 C6 -119.7(3) . . . . ?
Ir1 P2 O3 C6 0.8(3) . . . . ?
P1 O2 C2 N1 5.0(4) . . . . ?
P1 O2 C2 C3 -175.0(3) . . . . ?
C6 N1 C2 O2 179.1(3) . . . . ?
Ir1 N1 C2 O2 -5.3(4) . . . . ?
C6 N1 C2 C3 -0.9(5) . . . . ?
Ir1 N1 C2 C3 174.7(3) . . . . ?
O2 C2 C3 C4 179.7(3) . . . . ?
N1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
P2 O3 C6 N1 -3.7(4) . . . . ?
P2 O3 C6 C5 175.8(3) . . . . ?
C2 N1 C6 O3 -179.3(3) . . . . ?
Ir1 N1 C6 O3 5.1(4) . . . . ?
C2 N1 C6 C5 1.3(5) . . . . ?
Ir1 N1 C6 C5 -174.3(3) . . . . ?
C4 C5 C6 O3 180.0(3) . . . . ?
C4 C5 C6 N1 -0.6(5) . . . . ?
O2 P1 C7 C10 -63.7(3) . . . . ?
C11 P1 C7 C10 43.0(4) . . . . ?
Ir1 P1 C7 C10 -172.4(3) . . . . ?
O2 P1 C7 C9 173.0(3) . . . . ?
C11 P1 C7 C9 -80.3(3) . . . . ?
Ir1 P1 C7 C9 64.3(3) . . . . ?
O2 P1 C7 C8 56.8(3) . . . . ?
C11 P1 C7 C8 163.5(3) . . . . ?
Ir1 P1 C7 C8 -51.9(3) . . . . ?
O2 P1 C11 C13 178.0(3) . . . . ?
C7 P1 C11 C13 70.2(4) . . . . ?
Ir1 P1 C11 C13 -73.8(3) . . . . ?
O2 P1 C11 C12 -65.4(3) . . . . ?
C7 P1 C11 C12 -173.1(3) . . . . ?
Ir1 P1 C11 C12 42.8(3) . . . . ?
O2 P1 C11 C14 53.0(3) . . . . ?
C7 P1 C11 C14 -54.7(4) . . . . ?
Ir1 P1 C11 C14 161.3(3) . . . . ?
O3 P2 C15 C17 -69.1(3) . . . . ?
C19 P2 C15 C17 -176.8(3) . . . . ?
Ir1 P2 C15 C17 38.8(3) . . . . ?
O3 P2 C15 C18 49.9(3) . . . . ?
C19 P2 C15 C18 -57.8(4) . . . . ?
Ir1 P2 C15 C18 157.8(3) . . . . ?
O3 P2 C15 C16 173.3(3) . . . . ?
C19 P2 C15 C16 65.6(3) . . . . ?
Ir1 P2 C15 C16 -78.8(3) . . . . ?
O3 P2 C19 C21 167.8(3) . . . . ?
C15 P2 C19 C21 -85.1(3) . . . . ?
Ir1 P2 C19 C21 59.1(3) . . . . ?
O3 P2 C19 C20 -68.4(3) . . . . ?
C15 P2 C19 C20 38.7(4) . . . . ?
Ir1 P2 C19 C20 -177.1(3) . . . . ?
O3 P2 C19 C22 49.3(3) . . . . ?
C15 P2 C19 C22 156.4(3) . . . . ?
Ir1 P2 C19 C22 -59.4(3) . . . . ?

_refine_diff_density_max         1.334
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.109



