# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1972605'
loop_
_audit_author_name
_audit_author_address
'Claudia Graiff'
;University of Parma
Italy
;
_audit_update_record             
;
2019-12-17 deposited with the CCDC.	2020-02-05 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         ?
_chemical_formula_sum            'C20 H27 Br2 Cl F6 Ir N4 P'
_chemical_formula_weight         855.89

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.798(3)
_cell_length_b                   12.135(2)
_cell_length_c                   15.460(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.923(3)
_cell_angle_gamma                90
_cell_volume                     2587.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      4
_cell_measurement_theta_max      19

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.197
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    8.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4724
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker APEX II SADABS, 2008'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41255
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.946
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7868
_reflns_number_gt                5527
_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       'APEX-II (2008)'
_computing_cell_refinement       'APEX-II (2008)'
_computing_data_reduction        'SAINT (2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5'
_computing_publication_material  
'PARST M. Nardelli, J.Appl.Crystallogr.1995,28,659'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+4.5883P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7868
_refine_ls_number_parameters     341
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.983
_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
C1 C 0.6392(4) 0.1261(4) 0.1223(3) 0.0359(11) Uani 1 1 d . . . . .
C2 C 0.5264(5) 0.2355(5) 0.2157(5) 0.0597(17) Uani 1 1 d . . . . .
H2A H 0.5250 0.2182 0.2762 0.089 Uiso 1 1 calc R U . . .
H2B H 0.4630 0.2580 0.1953 0.089 Uiso 1 1 calc R U . . .
H2C H 0.5717 0.2942 0.2070 0.089 Uiso 1 1 calc R U . . .
C3 C 0.5011(4) 0.0442(5) 0.1629(4) 0.0522(15) Uani 1 1 d . . . . .
C4 C 0.5461(5) -0.0273(5) 0.1159(5) 0.069(2) Uani 1 1 d . . . . .
H4 H 0.5252 -0.0983 0.1024 0.082 Uiso 1 1 calc R U . . .
C51 C 0.6952(7) -0.0533(6) 0.0438(6) 0.063(2) Uani 0.8 1 d D . P A 1
H51A H 0.7197 -0.1088 0.0840 0.075 Uiso 0.8 1 calc R U P A 1
H51B H 0.6578 -0.0907 -0.0016 0.075 Uiso 0.8 1 calc R U P A 1
C61 C 0.7784(6) 0.0032(6) 0.0048(5) 0.057(2) Uani 0.8 1 d D . P A 1
H61A H 0.7564 0.0703 -0.0237 0.068 Uiso 0.8 1 calc R U P A 1
H61B H 0.8065 -0.0442 -0.0382 0.068 Uiso 0.8 1 calc R U P A 1
C52 C 0.6934(15) 0.009(2) 0.0115(11) 0.045(7) Uani 0.2 1 d D . P A 2
H52A H 0.7130 0.0802 -0.0104 0.054 Uiso 0.2 1 calc R U P A 2
H52B H 0.6596 -0.0314 -0.0345 0.054 Uiso 0.2 1 calc R U P A 2
C62 C 0.7799(14) -0.0553(14) 0.0471(15) 0.031(5) Uani 0.2 1 d D . P A 2
H62A H 0.7621 -0.0997 0.0963 0.037 Uiso 0.2 1 calc R U P A 2
H62B H 0.8053 -0.1034 0.0031 0.037 Uiso 0.2 1 calc R U P A 2
C7 C 0.9356(5) -0.0303(6) 0.0967(5) 0.074(2) Uani 1 1 d . . . . .
H7 H 0.9516 -0.0999 0.0766 0.089 Uiso 1 1 calc R U . . .
C8 C 0.9866(4) 0.0300(5) 0.1523(4) 0.0551(16) Uani 1 1 d . . . . .
C9 C 0.9756(5) 0.2178(5) 0.2183(5) 0.0598(16) Uani 1 1 d . . . . .
H9A H 1.0401 0.2351 0.2013 0.090 Uiso 1 1 calc R U . . .
H9B H 0.9771 0.1963 0.2781 0.090 Uiso 1 1 calc R U . . .
H9C H 0.9349 0.2813 0.2104 0.090 Uiso 1 1 calc R U . . .
C10 C 0.8522(4) 0.1265(4) 0.1177(3) 0.0385(12) Uani 1 1 d . . . . .
C11 C 0.7363(4) 0.3064(4) -0.0232(3) 0.0388(12) Uani 1 1 d . . . . .
C12 C 0.6570(4) 0.3548(4) 0.0222(3) 0.0357(11) Uani 1 1 d . . . . .
C13 C 0.6969(4) 0.4184(4) 0.0906(3) 0.0350(11) Uani 1 1 d . . . . .
C14 C 0.8007(4) 0.4139(4) 0.0877(3) 0.0348(11) Uani 1 1 d . . . . .
C15 C 0.8252(4) 0.3479(4) 0.0163(3) 0.0379(11) Uani 1 1 d . . . . .
C16 C 0.7262(6) 0.2532(5) -0.1109(4) 0.067(2) Uani 1 1 d . . . . .
H16A H 0.6728 0.2025 -0.1117 0.101 Uiso 1 1 calc R U . . .
H16B H 0.7848 0.2142 -0.1230 0.101 Uiso 1 1 calc R U . . .
H16C H 0.7147 0.3089 -0.1542 0.101 Uiso 1 1 calc R U . . .
C17 C 0.5524(4) 0.3434(5) -0.0052(5) 0.0620(17) Uani 1 1 d . . . . .
H17A H 0.5125 0.3687 0.0405 0.093 Uiso 1 1 calc R U . . .
H17B H 0.5382 0.2675 -0.0175 0.093 Uiso 1 1 calc R U . . .
H17C H 0.5395 0.3868 -0.0562 0.093 Uiso 1 1 calc R U . . .
C18 C 0.6429(5) 0.4902(4) 0.1523(4) 0.0536(15) Uani 1 1 d . . . . .
H18A H 0.6485 0.5659 0.1351 0.080 Uiso 1 1 calc R U . . .
H18B H 0.6701 0.4811 0.2098 0.080 Uiso 1 1 calc R U . . .
H18C H 0.5758 0.4694 0.1512 0.080 Uiso 1 1 calc R U . . .
C19 C 0.8679(5) 0.4815(4) 0.1446(4) 0.0555(16) Uani 1 1 d . . . . .
H19A H 0.9336 0.4591 0.1362 0.083 Uiso 1 1 calc R U . . .
H19B H 0.8524 0.4707 0.2041 0.083 Uiso 1 1 calc R U . . .
H19C H 0.8607 0.5580 0.1299 0.083 Uiso 1 1 calc R U . . .
C20 C 0.9244(4) 0.3283(6) -0.0169(4) 0.0638(18) Uani 1 1 d . . . . .
H20A H 0.9381 0.3824 -0.0600 0.096 Uiso 1 1 calc R U . . .
H20B H 0.9272 0.2560 -0.0420 0.096 Uiso 1 1 calc R U . . .
H20C H 0.9715 0.3338 0.0300 0.096 Uiso 1 1 calc R U . . .
Br1 Br 0.38868(6) 0.02278(7) 0.22320(6) 0.0839(3) Uani 1 1 d . . . . .
Br2 Br 1.10068(5) -0.00600(7) 0.21371(6) 0.0862(3) Uani 1 1 d . . . . .
Cl Cl 0.75292(11) 0.25758(10) 0.26538(8) 0.0432(3) Uani 1 1 d . . . . .
F1 F 0.8448(4) 0.5816(4) -0.0828(3) 0.1182(19) Uani 1 1 d . . . . .
F2 F 0.7572(4) 0.6652(4) -0.1883(3) 0.1063(17) Uani 1 1 d . . . . .
F3 F 0.6753(4) 0.7546(3) -0.0885(4) 0.0977(16) Uani 1 1 d . . . . .
F4 F 0.7573(4) 0.6665(5) 0.0142(3) 0.1159(18) Uani 1 1 d . . . . .
F5 F 0.8348(4) 0.7633(4) -0.0832(4) 0.1130(19) Uani 1 1 d . . . . .
F6 F 0.6846(5) 0.5712(4) -0.0889(4) 0.137(2) Uani 1 1 d . . . . .
Ir Ir 0.74591(2) 0.24360(2) 0.10859(2) 0.02873(6) Uani 1 1 d . . . . .
N1 N 0.5562(3) 0.1380(3) 0.1677(3) 0.0395(10) Uani 1 1 d . . . . .
N2 N 0.6303(4) 0.0218(4) 0.0900(3) 0.0569(13) Uani 1 1 d D . . . .
N3 N 0.8530(4) 0.0301(4) 0.0738(4) 0.0610(14) Uani 1 1 d D . . . .
N4 N 0.9371(3) 0.1269(3) 0.1649(3) 0.0410(10) Uani 1 1 d . . . . .
P P 0.75970(13) 0.66712(12) -0.08631(10) 0.0517(4) 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
C1 N2 1.365(6) . ?
C1 N1 1.370(6) . ?
C1 Ir 2.066(5) . ?
C2 N1 1.463(7) . ?
C3 C4 1.302(9) . ?
C3 N1 1.369(6) . ?
C3 Br1 1.855(6) . ?
C4 N2 1.378(8) . ?
C51 C61 1.482(10) . ?
C51 N2 1.477(8) . ?
C61 N3 1.494(8) . ?
C52 N2 1.525(15) . ?
C52 C62 1.514(18) . ?
C62 N3 1.495(14) . ?
C7 C8 1.314(10) . ?
C7 N3 1.391(8) . ?
C8 N4 1.377(7) . ?
C8 Br2 1.863(6) . ?
C9 N4 1.467(7) . ?
C10 N3 1.352(6) . ?
C10 N4 1.360(6) . ?
C10 Ir 2.043(5) . ?
C11 C12 1.445(7) . ?
C11 C15 1.442(7) . ?
C11 C16 1.505(7) . ?
C11 Ir 2.175(5) . ?
C12 C13 1.406(7) . ?
C12 C17 1.496(7) . ?
C12 Ir 2.236(5) . ?
C13 C14 1.436(7) . ?
C13 C18 1.507(7) . ?
C13 Ir 2.241(5) . ?
C14 C15 1.414(7) . ?
C14 C19 1.500(7) . ?
C14 Ir 2.228(4) . ?
C15 C20 1.497(7) . ?
C15 Ir 2.223(5) . ?
Cl Ir 2.4286(13) . ?
F1 P 1.566(5) . ?
F2 P 1.577(4) . ?
F3 P 1.576(5) . ?
F4 P 1.555(5) . ?
F5 P 1.561(5) . ?
F6 P 1.558(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 102.7(4) . . ?
N2 C1 Ir 131.1(4) . . ?
N1 C1 Ir 126.2(3) . . ?
C4 C3 N1 108.0(5) . . ?
C4 C3 Br1 127.5(5) . . ?
N1 C3 Br1 124.2(5) . . ?
C3 C4 N2 107.3(5) . . ?
C61 C51 N2 113.7(6) . . ?
C51 C61 N3 109.6(7) . . ?
N2 C52 C62 103.1(15) . . ?
N3 C62 C52 105.0(14) . . ?
C8 C7 N3 106.8(6) . . ?
C7 C8 N4 108.1(5) . . ?
C7 C8 Br2 128.9(5) . . ?
N4 C8 Br2 122.9(5) . . ?
N3 C10 N4 104.5(4) . . ?
N3 C10 Ir 125.8(4) . . ?
N4 C10 Ir 129.7(4) . . ?
C12 C11 C15 107.5(4) . . ?
C12 C11 C16 124.3(5) . . ?
C15 C11 C16 125.6(5) . . ?
C12 C11 Ir 73.2(3) . . ?
C15 C11 Ir 72.7(3) . . ?
C16 C11 Ir 134.0(3) . . ?
C13 C12 C11 107.7(4) . . ?
C13 C12 C17 127.8(5) . . ?
C11 C12 C17 124.3(5) . . ?
C13 C12 Ir 71.9(3) . . ?
C11 C12 Ir 68.6(3) . . ?
C17 C12 Ir 128.2(4) . . ?
C12 C13 C14 108.8(4) . . ?
C12 C13 C18 127.1(5) . . ?
C14 C13 C18 123.8(5) . . ?
C12 C13 Ir 71.5(3) . . ?
C14 C13 Ir 70.8(3) . . ?
C18 C13 Ir 128.5(4) . . ?
C15 C14 C13 108.1(4) . . ?
C15 C14 C19 127.5(5) . . ?
C13 C14 C19 123.9(5) . . ?
C15 C14 Ir 71.3(3) . . ?
C13 C14 Ir 71.7(2) . . ?
C19 C14 Ir 128.9(4) . . ?
C14 C15 C11 107.8(4) . . ?
C14 C15 C20 127.1(5) . . ?
C11 C15 C20 125.0(5) . . ?
C14 C15 Ir 71.7(3) . . ?
C11 C15 Ir 69.1(3) . . ?
C20 C15 Ir 127.2(4) . . ?
C10 Ir C1 91.4(2) . . ?
C10 Ir C11 109.24(19) . . ?
C1 Ir C11 108.5(2) . . ?
C10 Ir C15 94.18(19) . . ?
C1 Ir C15 145.79(19) . . ?
C11 Ir C15 38.27(19) . . ?
C10 Ir C14 114.13(19) . . ?
C1 Ir C14 154.41(19) . . ?
C11 Ir C14 63.22(18) . . ?
C15 Ir C14 37.05(18) . . ?
C10 Ir C12 147.0(2) . . ?
C1 Ir C12 95.68(18) . . ?
C11 Ir C12 38.21(18) . . ?
C15 Ir C12 62.95(19) . . ?
C14 Ir C12 62.36(17) . . ?
C10 Ir C13 151.6(2) . . ?
C1 Ir C13 116.94(19) . . ?
C11 Ir C13 62.82(17) . . ?
C15 Ir C13 62.25(18) . . ?
C14 Ir C13 37.49(18) . . ?
C12 Ir C13 36.62(17) . . ?
C10 Ir Cl 88.58(15) . . ?
C1 Ir Cl 87.16(14) . . ?
C11 Ir Cl 155.43(13) . . ?
C15 Ir Cl 126.65(14) . . ?
C14 Ir Cl 94.44(13) . . ?
C12 Ir Cl 123.82(13) . . ?
C13 Ir Cl 93.41(13) . . ?
C3 N1 C1 110.9(5) . . ?
C3 N1 C2 122.3(5) . . ?
C1 N1 C2 126.8(4) . . ?
C1 N2 C4 111.1(5) . . ?
C1 N2 C52 109.8(10) . . ?
C4 N2 C52 134.2(10) . . ?
C1 N2 C51 134.5(6) . . ?
C4 N2 C51 113.9(5) . . ?
C10 N3 C7 110.4(6) . . ?
C10 N3 C62 136.2(10) . . ?
C7 N3 C62 104.1(9) . . ?
C10 N3 C61 122.1(5) . . ?
C7 N3 C61 127.3(5) . . ?
C10 N4 C8 110.1(5) . . ?
C10 N4 C9 126.5(4) . . ?
C8 N4 C9 123.4(5) . . ?
F4 P F6 89.1(3) . . ?
F4 P F5 90.5(3) . . ?
F6 P F5 179.7(4) . . ?
F4 P F1 90.2(3) . . ?
F6 P F1 90.2(4) . . ?
F5 P F1 89.9(3) . . ?
F4 P F2 177.3(3) . . ?
F6 P F2 88.4(3) . . ?
F5 P F2 92.0(3) . . ?
F1 P F2 90.9(3) . . ?
F4 P F3 89.1(3) . . ?
F6 P F3 90.7(3) . . ?
F5 P F3 89.2(3) . . ?
F1 P F3 178.9(3) . . ?
F2 P F3 89.8(3) . . ?

_refine_diff_density_max         1.449
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.148

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1972606'
loop_
_audit_author_name
_audit_author_address
'Claudia Graiff'
;University of Parma
Italy
;
_audit_update_record             
;
2019-12-17 deposited with the CCDC.	2020-02-05 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         ?
_chemical_formula_sum            'C28 H33 Cl F6 Ir N4 P'
_chemical_formula_weight         798.20

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'
Cl Cl 0.1484 0.1585 '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'
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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.439(3)
_cell_length_b                   12.898(3)
_cell_length_c                   15.652(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.895(3)
_cell_angle_gamma                90
_cell_volume                     2911.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      5
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    4.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5985
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker APEX II SADABS, 2008'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44448
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.872
_diffrn_reflns_theta_max         30.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8807
_reflns_number_gt                6324
_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       'APEX-II (2008)'
_computing_cell_refinement       'APEX-II (2008)'
_computing_data_reduction        'SAINT (2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5'
_computing_publication_material  
'PARST M. Nardelli, J.Appl.Crystallogr.1995,28,659'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0215P)²+2.9691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8807
_refine_ls_number_parameters     377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0613
_refine_ls_wR_factor_gt          0.0518
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_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
Cl Cl 0.82212(7) 0.26626(8) 0.18966(6) 0.0525(2) Uani 1 1 d . . . . .
N3 N 0.66352(18) 0.0715(2) 0.04077(16) 0.0325(6) Uani 1 1 d . . . . .
N4 N 0.61405(19) 0.1666(2) 0.14305(17) 0.0358(6) Uani 1 1 d . . . . .
C1 C 0.6327(2) 0.4010(2) 0.0123(2) 0.0365(7) Uani 1 1 d . . . . .
C2 C 0.6880(3) 0.4521(3) 0.0760(2) 0.0438(8) Uani 1 1 d . . . . .
C3 C 0.7796(2) 0.4656(3) 0.0445(2) 0.0421(8) Uani 1 1 d . . . . .
C4 C 0.7790(2) 0.4266(3) -0.0390(2) 0.0377(8) Uani 1 1 d . . . . .
C5 C 0.6893(2) 0.3819(2) -0.0596(2) 0.0328(7) Uani 1 1 d . . . . .
C6 C 0.5314(2) 0.3725(3) 0.0130(3) 0.0540(10) Uani 1 1 d . . . . .
H6A H 0.5075 0.3925 0.0666 0.081 Uiso 1 1 calc R U . . .
H6B H 0.5246 0.2989 0.0055 0.081 Uiso 1 1 calc R U . . .
H6C H 0.4978 0.4078 -0.0328 0.081 Uiso 1 1 calc R U . . .
C7 C 0.6541(3) 0.3546(3) -0.1480(2) 0.0502(9) Uani 1 1 d . . . . .
H7A H 0.6329 0.4162 -0.1773 0.075 Uiso 1 1 calc R U . . .
H7B H 0.6038 0.3064 -0.1452 0.075 Uiso 1 1 calc R U . . .
H7C H 0.7032 0.3237 -0.1784 0.075 Uiso 1 1 calc R U . . .
C8 C 0.8566(3) 0.4328(3) -0.1002(3) 0.0566(11) Uani 1 1 d . . . . .
H8A H 0.8488 0.4938 -0.1350 0.085 Uiso 1 1 calc R U . . .
H8B H 0.8552 0.3725 -0.1361 0.085 Uiso 1 1 calc R U . . .
H8C H 0.9151 0.4362 -0.0683 0.085 Uiso 1 1 calc R U . . .
C9 C 0.8559(3) 0.5247(3) 0.0920(3) 0.0664(13) Uani 1 1 d . . . . .
H9A H 0.9134 0.5133 0.0651 0.100 Uiso 1 1 calc R U . . .
H9B H 0.8615 0.5012 0.1502 0.100 Uiso 1 1 calc R U . . .
H9C H 0.8415 0.5974 0.0908 0.100 Uiso 1 1 calc R U . . .
C10 C 0.6579(4) 0.4976(3) 0.1588(3) 0.0658(13) Uani 1 1 d . . . . .
H10A H 0.6585 0.5719 0.1551 0.099 Uiso 1 1 calc R U . . .
H10B H 0.6998 0.4756 0.2048 0.099 Uiso 1 1 calc R U . . .
H10C H 0.5964 0.4743 0.1692 0.099 Uiso 1 1 calc R U . . .
C11 C 0.8507(2) 0.2070(3) -0.0019(2) 0.0338(7) Uani 1 1 d . . . . .
C12 C 0.9974(3) 0.2838(3) 0.0668(3) 0.0512(10) Uani 1 1 d . . . . .
H12A H 1.0356 0.3282 0.0342 0.077 Uiso 1 1 calc R U . . .
H12B H 1.0360 0.2436 0.1061 0.077 Uiso 1 1 calc R U . . .
H12C H 0.9555 0.3251 0.0981 0.077 Uiso 1 1 calc R U . . .
C13 C 0.9883(2) 0.1453(3) -0.0439(2) 0.0383(8) Uani 1 1 d . . . . .
C14 C 1.0815(2) 0.1242(3) -0.0553(2) 0.0494(9) Uani 1 1 d . . . . .
H14 H 1.1287 0.1610 -0.0263 0.059 Uiso 1 1 calc R U . . .
C15 C 1.0999(3) 0.0459(4) -0.1121(2) 0.0563(11) Uani 1 1 d . . . . .
H15 H 1.1613 0.0295 -0.1216 0.068 Uiso 1 1 calc R U . . .
C16 C 1.0300(3) -0.0088(3) -0.1551(2) 0.0535(10) Uani 1 1 d . . . . .
H16 H 1.0458 -0.0619 -0.1919 0.064 Uiso 1 1 calc R U . . .
C17 C 0.9370(3) 0.0125(3) -0.1455(2) 0.0453(9) Uani 1 1 d . . . . .
H17 H 0.8901 -0.0243 -0.1748 0.054 Uiso 1 1 calc R U . . .
C18 C 0.9183(2) 0.0919(3) -0.0893(2) 0.0364(7) Uani 1 1 d . . . . .
C19 C 0.7434(2) 0.1015(3) -0.0961(2) 0.0362(7) Uani 1 1 d . . . . .
H19A H 0.7487 0.0695 -0.1518 0.043 Uiso 1 1 calc R U . . .
H19B H 0.7042 0.1623 -0.1036 0.043 Uiso 1 1 calc R U . . .
C20 C 0.6989(2) 0.0264(3) -0.0376(2) 0.0374(7) Uani 1 1 d . . . . .
H20A H 0.6479 -0.0073 -0.0692 0.045 Uiso 1 1 calc R U . . .
H20B H 0.7440 -0.0267 -0.0212 0.045 Uiso 1 1 calc R U . . .
C21 C 0.6714(2) 0.1683(3) 0.0758(2) 0.0322(7) Uani 1 1 d . . . . .
C22 C 0.5984(3) 0.2487(3) 0.2048(2) 0.0514(10) Uani 1 1 d . . . . .
H22A H 0.6372 0.3070 0.1933 0.077 Uiso 1 1 calc R U . . .
H22B H 0.6131 0.2236 0.2616 0.077 Uiso 1 1 calc R U . . .
H22C H 0.5345 0.2697 0.2000 0.077 Uiso 1 1 calc R U . . .
C23 C 0.5726(2) 0.0703(3) 0.1513(2) 0.0365(7) Uani 1 1 d . . . . .
C24 C 0.5105(2) 0.0329(3) 0.2090(2) 0.0473(9) Uani 1 1 d . . . . .
H24 H 0.4857 0.0756 0.2499 0.057 Uiso 1 1 calc R U . . .
C25 C 0.4877(3) -0.0696(3) 0.2024(3) 0.0577(11) Uani 1 1 d . . . . .
H25 H 0.4477 -0.0980 0.2408 0.069 Uiso 1 1 calc R U . . .
C26 C 0.5228(3) -0.1321(4) 0.1400(3) 0.0642(12) Uani 1 1 d . . . . .
H26 H 0.5067 -0.2019 0.1384 0.077 Uiso 1 1 calc R U . . .
C27 C 0.5811(3) -0.0943(3) 0.0799(3) 0.0530(10) Uani 1 1 d . . . . .
H27 H 0.6027 -0.1359 0.0366 0.064 Uiso 1 1 calc R U . . .
C28 C 0.6051(2) 0.0090(3) 0.0879(2) 0.0362(7) Uani 1 1 d . . . . .
Ir Ir 0.75105(2) 0.29527(2) 0.04830(2) 0.03020(4) Uani 1 1 d . . . . .
N1 N 0.94484(18) 0.2147(2) 0.00942(18) 0.0377(6) Uani 1 1 d . . . . .
N2 N 0.83528(18) 0.1334(2) -0.06275(17) 0.0343(6) Uani 1 1 d . . . . .
F1 F 0.2432(2) 0.1678(2) 0.1507(2) 0.1032(11) Uani 1 1 d . . . . .
F2 F 0.3421(2) 0.3845(2) 0.1398(2) 0.0979(10) Uani 1 1 d . . . . .
F3 F 0.2060(2) 0.3272(3) 0.1880(2) 0.1031(11) Uani 1 1 d . . . . .
F4 F 0.37911(19) 0.2233(2) 0.1059(2) 0.0833(9) Uani 1 1 d . . . . .
F5 F 0.2458(2) 0.2945(3) 0.0549(2) 0.1275(16) Uani 1 1 d . . . . .
F6 F 0.3383(2) 0.2598(3) 0.23845(18) 0.0920(9) Uani 1 1 d . . . . .
P P 0.29244(7) 0.27678(8) 0.14594(7) 0.0471(2) 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
Cl Ir 2.4205(10) . ?
N3 C21 1.366(4) . ?
N3 C28 1.402(4) . ?
N3 C20 1.472(4) . ?
N4 C21 1.372(4) . ?
N4 C23 1.388(4) . ?
N4 C22 1.459(4) . ?
C1 C2 1.409(5) . ?
C1 C5 1.444(4) . ?
C1 C6 1.509(5) . ?
C1 Ir 2.236(3) . ?
C2 C3 1.446(5) . ?
C2 C10 1.506(5) . ?
C2 Ir 2.270(3) . ?
C3 C4 1.399(5) . ?
C3 C9 1.506(5) . ?
C3 Ir 2.237(3) . ?
C4 C5 1.439(5) . ?
C4 C8 1.513(5) . ?
C4 Ir 2.226(3) . ?
C5 C7 1.493(5) . ?
C5 Ir 2.178(3) . ?
C11 N2 1.356(4) . ?
C11 N1 1.365(4) . ?
C11 Ir 2.024(3) . ?
C12 N1 1.453(4) . ?
C13 C18 1.389(5) . ?
C13 C14 1.393(5) . ?
C13 N1 1.394(4) . ?
C14 C15 1.380(6) . ?
C15 C16 1.379(6) . ?
C16 C17 1.386(5) . ?
C17 C18 1.385(5) . ?
C18 N2 1.395(4) . ?
C19 N2 1.460(4) . ?
C19 C20 1.500(5) . ?
C21 Ir 2.059(3) . ?
C23 C28 1.371(5) . ?
C23 C24 1.390(5) . ?
C24 C25 1.365(5) . ?
C25 C26 1.382(6) . ?
C26 C27 1.382(5) . ?
C27 C28 1.381(5) . ?
F1 P 1.579(3) . ?
F2 P 1.569(3) . ?
F3 P 1.580(3) . ?
F4 P 1.586(3) . ?
F5 P 1.562(3) . ?
F6 P 1.577(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
C21 N3 C28 110.8(3) . . ?
C21 N3 C20 132.0(3) . . ?
C28 N3 C20 117.0(3) . . ?
C21 N4 C23 111.5(3) . . ?
C21 N4 C22 128.0(3) . . ?
C23 N4 C22 120.4(3) . . ?
C2 C1 C5 108.0(3) . . ?
C2 C1 C6 128.5(3) . . ?
C5 C1 C6 123.4(3) . . ?
C2 C1 Ir 73.1(2) . . ?
C5 C1 Ir 68.74(17) . . ?
C6 C1 Ir 125.3(2) . . ?
C1 C2 C3 108.0(3) . . ?
C1 C2 C10 127.9(4) . . ?
C3 C2 C10 123.7(4) . . ?
C1 C2 Ir 70.47(19) . . ?
C3 C2 Ir 70.05(19) . . ?
C10 C2 Ir 130.3(3) . . ?
C4 C3 C2 108.2(3) . . ?
C4 C3 C9 127.8(4) . . ?
C2 C3 C9 123.5(4) . . ?
C4 C3 Ir 71.32(19) . . ?
C2 C3 Ir 72.54(19) . . ?
C9 C3 Ir 128.0(3) . . ?
C3 C4 C5 108.4(3) . . ?
C3 C4 C8 127.0(3) . . ?
C5 C4 C8 124.5(3) . . ?
C3 C4 Ir 72.1(2) . . ?
C5 C4 Ir 69.13(17) . . ?
C8 C4 Ir 126.3(3) . . ?
C4 C5 C1 107.2(3) . . ?
C4 C5 C7 124.2(3) . . ?
C1 C5 C7 125.7(3) . . ?
C4 C5 Ir 72.76(18) . . ?
C1 C5 Ir 73.10(18) . . ?
C7 C5 Ir 134.8(2) . . ?
N2 C11 N1 105.6(3) . . ?
N2 C11 Ir 124.9(2) . . ?
N1 C11 Ir 129.2(2) . . ?
C18 C13 C14 121.3(3) . . ?
C18 C13 N1 106.7(3) . . ?
C14 C13 N1 132.0(3) . . ?
C13 C14 C15 116.4(4) . . ?
C16 C15 C14 121.9(4) . . ?
C15 C16 C17 122.3(4) . . ?
C18 C17 C16 115.9(4) . . ?
C17 C18 C13 122.1(3) . . ?
C17 C18 N2 132.2(3) . . ?
C13 C18 N2 105.7(3) . . ?
N2 C19 C20 111.8(3) . . ?
N3 C20 C19 115.6(3) . . ?
N3 C21 N4 104.6(3) . . ?
N3 C21 Ir 132.8(2) . . ?
N4 C21 Ir 122.5(2) . . ?
C28 C23 N4 106.5(3) . . ?
C28 C23 C24 121.7(3) . . ?
N4 C23 C24 131.8(3) . . ?
C25 C24 C23 116.6(4) . . ?
C24 C25 C26 121.5(4) . . ?
C25 C26 C27 122.2(4) . . ?
C26 C27 C28 115.9(4) . . ?
C23 C28 N3 106.6(3) . . ?
C23 C28 C27 121.9(3) . . ?
N3 C28 C27 131.5(3) . . ?
C11 Ir C21 92.85(13) . . ?
C11 Ir C5 105.01(12) . . ?
C21 Ir C5 111.03(12) . . ?
C11 Ir C4 92.02(12) . . ?
C21 Ir C4 148.62(13) . . ?
C5 Ir C4 38.12(12) . . ?
C11 Ir C3 113.97(13) . . ?
C21 Ir C3 153.17(13) . . ?
C5 Ir C3 62.85(12) . . ?
C4 Ir C3 36.55(12) . . ?
C11 Ir C1 142.59(12) . . ?
C21 Ir C1 96.31(12) . . ?
C5 Ir C1 38.17(12) . . ?
C4 Ir C1 62.66(12) . . ?
C3 Ir C1 62.19(12) . . ?
C11 Ir C2 151.09(13) . . ?
C21 Ir C2 115.80(14) . . ?
C5 Ir C2 62.49(12) . . ?
C4 Ir C2 61.69(13) . . ?
C3 Ir C2 37.41(13) . . ?
C1 Ir C2 36.44(13) . . ?
C11 Ir Cl 89.47(9) . . ?
C21 Ir Cl 84.37(9) . . ?
C5 Ir Cl 157.83(9) . . ?
C4 Ir Cl 126.67(9) . . ?
C3 Ir Cl 96.10(10) . . ?
C1 Ir Cl 127.45(9) . . ?
C2 Ir Cl 96.83(10) . . ?
C11 N1 C13 110.6(3) . . ?
C11 N1 C12 127.6(3) . . ?
C13 N1 C12 121.8(3) . . ?
C11 N2 C18 111.4(3) . . ?
C11 N2 C19 124.3(3) . . ?
C18 N2 C19 124.3(3) . . ?
F5 P F2 89.5(2) . . ?
F5 P F1 90.0(2) . . ?
F2 P F1 179.08(18) . . ?
F5 P F6 179.1(2) . . ?
F2 P F6 90.40(19) . . ?
F1 P F6 90.11(19) . . ?
F5 P F3 90.3(2) . . ?
F2 P F3 91.94(19) . . ?
F1 P F3 88.83(18) . . ?
F6 P F3 88.79(18) . . ?
F5 P F4 90.9(2) . . ?
F2 P F4 89.37(16) . . ?
F1 P F4 89.87(16) . . ?
F6 P F4 89.97(18) . . ?
F3 P F4 178.20(19) . . ?

_refine_diff_density_max         0.932
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.112

