# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_nov_icp1b
_database_code_depnum_ccdc_archive 'CCDC 1833342'
loop_
_audit_author_name
_audit_author_address
'Banele Vatsha'
;University of Johannesburg
South Africa
;
_audit_update_record             
;
2020-04-11 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_audit_creation_date             2018-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 Cl Ir N2 O2, F6 P'
_chemical_formula_sum            'C23 H25 Cl F6 Ir N2 O2 P'
_chemical_formula_weight         734.07
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.9192(12)
_cell_length_b                   19.809(2)
_cell_length_c                   11.7104(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.931(3)
_cell_angle_gamma                90
_cell_volume                     2526.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.405
_shelx_estimated_absorpt_T_min   0.288
_exptl_absorpt_coefficient_mu    5.522
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            91002
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.620
_diffrn_reflns_theta_min         1.869
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5128
_reflns_number_total             5846
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.428
_refine_diff_density_min         -1.545
_refine_diff_density_rms         0.233
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.202
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+8.5011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C12(H12), C11(H11), C4(H4), C13(H13), C3(H3), C10(H10), C5(H5)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C23(H23A,H23B,
 H23C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.27246(2) 0.69370(2) 0.33013(2) 0.01416(8) Uani 1 1 d . . . . .
Cl1 Cl 0.34950(10) 0.71916(6) 0.14941(9) 0.0200(2) Uani 1 1 d . . . . .
P1 P 0.78806(12) 0.61947(8) 0.93614(12) 0.0255(3) Uani 1 1 d . . . . .
F3 F 0.9030(3) 0.6693(2) 0.9475(3) 0.0402(9) Uani 1 1 d . . . . .
O1 O 0.9027(3) 0.5261(2) 0.3926(3) 0.0248(8) Uani 1 1 d . . . . .
F2 F 0.7256(3) 0.6580(2) 1.0367(3) 0.0405(9) Uani 1 1 d . . . . .
F5 F 0.6732(3) 0.5687(2) 0.9264(4) 0.0541(12) Uani 1 1 d . . . . .
F6 F 0.8482(3) 0.5804(2) 0.8345(3) 0.0479(10) Uani 1 1 d . . . . .
F1 F 0.8572(3) 0.5706(2) 1.0265(4) 0.0438(9) Uani 1 1 d . . . . .
N2 N 0.2532(4) 0.7993(2) 0.3487(4) 0.0165(8) Uani 1 1 d . . . . .
O2 O 0.9058(3) 0.5503(2) 0.5795(3) 0.0286(8) Uani 1 1 d . . . . .
F4 F 0.7195(4) 0.6682(3) 0.8446(3) 0.0565(12) Uani 1 1 d . . . . .
N1 N 0.4456(3) 0.7253(2) 0.3947(3) 0.0164(8) Uani 1 1 d . . . . .
C7 C 0.5494(4) 0.6821(2) 0.4182(4) 0.0154(9) Uani 1 1 d . . . . .
C8 C 0.4617(4) 0.7889(3) 0.4103(4) 0.0180(9) Uani 1 1 d . . . . .
H8 H 0.539017 0.806567 0.438072 0.022 Uiso 1 1 calc R . . . .
C9 C 0.3569(4) 0.8330(3) 0.3839(4) 0.0190(9) Uani 1 1 d . . . . .
C6 C 0.5882(5) 0.6432(3) 0.3277(4) 0.0224(10) Uani 1 1 d . . . . .
H6 H 0.545996 0.644894 0.254016 0.027 Uiso 1 1 calc R . . . .
C14 C 0.0864(4) 0.6539(3) 0.3173(4) 0.0190(9) Uani 1 1 d . . . . .
C21 C 0.3532(5) 0.5321(3) 0.3162(5) 0.0249(11) Uani 1 1 d . . . . .
H21A H 0.382994 0.540033 0.240357 0.037 Uiso 1 1 calc GR . . . .
H21B H 0.315539 0.487208 0.318227 0.037 Uiso 1 1 calc GR . . . .
H21C H 0.422087 0.534607 0.374267 0.037 Uiso 1 1 calc GR . . . .
C12 C 0.1478(4) 0.9047(3) 0.3351(4) 0.0211(10) Uani 1 1 d . . . . .
H12 H 0.073229 0.929051 0.321978 0.025 Uiso 1 1 calc R . . . .
C19 C -0.0292(4) 0.6848(3) 0.2646(5) 0.0232(11) Uani 1 1 d . . . . .
H19A H -0.063477 0.715660 0.319556 0.035 Uiso 1 1 calc GR . . . .
H19B H -0.088873 0.649170 0.243988 0.035 Uiso 1 1 calc GR . . . .
H19C H -0.010891 0.709958 0.195679 0.035 Uiso 1 1 calc GR . . . .
C20 C 0.1470(5) 0.5884(3) 0.1383(4) 0.0248(11) Uani 1 1 d . . . . .
H20A H 0.109565 0.625665 0.093191 0.037 Uiso 1 1 calc GR . . . .
H20B H 0.093563 0.548713 0.131027 0.037 Uiso 1 1 calc GR . . . .
H20C H 0.227104 0.577520 0.110081 0.037 Uiso 1 1 calc GR . . . .
C11 C 0.2569(4) 0.9373(3) 0.3644(5) 0.0249(11) Uani 1 1 d . . . . .
H11 H 0.258586 0.985266 0.365344 0.030 Uiso 1 1 calc R . . . .
C1 C 0.8605(4) 0.5551(2) 0.4755(4) 0.0186(9) Uani 1 1 d . . . . .
C4 C 0.6085(5) 0.6800(3) 0.5267(4) 0.0201(10) Uani 1 1 d . . . . .
H4 H 0.580105 0.706713 0.586855 0.024 Uiso 1 1 calc R . . . .
C13 C 0.1510(4) 0.8352(3) 0.3256(4) 0.0200(10) Uani 1 1 d . . . . .
H13 H 0.077470 0.812075 0.301653 0.024 Uiso 1 1 calc R . . . .
C18 C 0.1330(4) 0.6575(2) 0.4362(4) 0.0170(9) Uani 1 1 d . . . . .
C3 C 0.7097(4) 0.6382(3) 0.5464(4) 0.0203(10) Uani 1 1 d . . . . .
H3 H 0.750832 0.635876 0.620432 0.024 Uiso 1 1 calc R . . . .
C23 C 0.0757(5) 0.6964(3) 0.5281(5) 0.0206(10) Uani 1 1 d . . . . .
H23A H 0.140185 0.718108 0.577641 0.031 Uiso 1 1 calc GR . . . .
H23B H 0.028577 0.665609 0.573718 0.031 Uiso 1 1 calc GR . . . .
H23C H 0.020938 0.730972 0.493226 0.031 Uiso 1 1 calc GR . . . .
C16 C 0.2597(4) 0.5846(3) 0.3405(4) 0.0169(9) Uani 1 1 d . . . . .
C2 C 0.7510(4) 0.5996(2) 0.4572(4) 0.0195(10) Uani 1 1 d . . . . .
C10 C 0.3622(5) 0.9025(3) 0.3921(4) 0.0209(10) Uani 1 1 d . . . . .
H10 H 0.436267 0.925111 0.416100 0.025 Uiso 1 1 calc R . . . .
C22 C 0.3125(5) 0.6011(3) 0.5610(4) 0.0219(10) Uani 1 1 d . . . . .
H22A H 0.395181 0.586333 0.544696 0.033 Uiso 1 1 calc GR . . . .
H22B H 0.272473 0.565589 0.603294 0.033 Uiso 1 1 calc GR . . . .
H22C H 0.318059 0.642389 0.607130 0.033 Uiso 1 1 calc GR . . . .
C17 C 0.2389(4) 0.6147(2) 0.4508(4) 0.0163(9) Uani 1 1 d . . . . .
C15 C 0.1635(4) 0.6089(3) 0.2610(4) 0.0195(10) Uani 1 1 d . . . . .
C5 C 0.6892(4) 0.6025(3) 0.3486(4) 0.0213(10) Uani 1 1 d . . . . .
H5 H 0.717510 0.575840 0.288289 0.026 Uiso 1 1 calc R . . . .
H2 H 0.964(8) 0.520(5) 0.594(7) 0.07(3) Uiso 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 Cl1 2.3843(11) . ?
Ir1 N2 2.115(4) . ?
Ir1 N1 2.084(4) . ?
Ir1 C14 2.175(5) . ?
Ir1 C18 2.153(4) . ?
Ir1 C16 2.169(5) . ?
Ir1 C17 2.156(5) . ?
Ir1 C15 2.182(5) . ?
P1 F3 1.594(4) . ?
P1 F2 1.595(4) . ?
P1 F5 1.606(4) . ?
P1 F6 1.598(4) . ?
P1 F1 1.587(4) . ?
P1 F4 1.591(4) . ?
O1 C1 1.243(6) . ?
N2 C9 1.354(6) . ?
N2 C13 1.336(6) . ?
O2 C1 1.287(6) . ?
O2 H2 0.89(9) . ?
N1 C7 1.431(6) . ?
N1 C8 1.284(7) . ?
C7 C6 1.400(7) . ?
C7 C4 1.386(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.456(7) . ?
C9 C10 1.381(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.375(7) . ?
C14 C19 1.498(7) . ?
C14 C18 1.451(7) . ?
C14 C15 1.419(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 C16 1.499(7) . ?
C12 H12 0.9500 . ?
C12 C11 1.377(7) . ?
C12 C13 1.381(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C15 1.492(7) . ?
C11 H11 0.9500 . ?
C11 C10 1.361(7) . ?
C1 C2 1.489(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.387(7) . ?
C13 H13 0.9500 . ?
C18 C23 1.495(7) . ?
C18 C17 1.434(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.393(7) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C16 C17 1.455(6) . ?
C16 C15 1.438(6) . ?
C2 C5 1.400(7) . ?
C10 H10 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 C17 1.497(6) . ?
C5 H5 0.9500 . ?

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 Ir1 Cl1 85.74(12) . . ?
N2 Ir1 C14 105.47(17) . . ?
N2 Ir1 C18 100.97(18) . . ?
N2 Ir1 C16 166.43(18) . . ?
N2 Ir1 C17 128.85(17) . . ?
N2 Ir1 C15 138.08(17) . . ?
N1 Ir1 Cl1 83.79(11) . . ?
N1 Ir1 N2 76.09(16) . . ?
N1 Ir1 C14 162.57(17) . . ?
N1 Ir1 C18 123.42(16) . . ?
N1 Ir1 C16 109.82(16) . . ?
N1 Ir1 C17 99.84(16) . . ?
N1 Ir1 C15 145.49(17) . . ?
C14 Ir1 Cl1 113.58(13) . . ?
C14 Ir1 C15 38.01(18) . . ?
C18 Ir1 Cl1 152.77(13) . . ?
C18 Ir1 C14 39.19(17) . . ?
C18 Ir1 C16 65.51(18) . . ?
C18 Ir1 C17 38.89(18) . . ?
C18 Ir1 C15 64.45(18) . . ?
C16 Ir1 Cl1 106.78(13) . . ?
C16 Ir1 C14 65.12(18) . . ?
C16 Ir1 C15 38.59(17) . . ?
C17 Ir1 Cl1 145.24(13) . . ?
C17 Ir1 C14 65.32(18) . . ?
C17 Ir1 C16 39.30(17) . . ?
C17 Ir1 C15 64.65(18) . . ?
C15 Ir1 Cl1 92.88(13) . . ?
F3 P1 F2 90.9(2) . . ?
F3 P1 F5 179.1(3) . . ?
F3 P1 F6 90.0(2) . . ?
F2 P1 F5 88.9(2) . . ?
F2 P1 F6 179.0(2) . . ?
F6 P1 F5 90.1(2) . . ?
F1 P1 F3 89.2(2) . . ?
F1 P1 F2 90.4(2) . . ?
F1 P1 F5 90.0(2) . . ?
F1 P1 F6 90.0(2) . . ?
F1 P1 F4 179.5(2) . . ?
F4 P1 F3 90.7(3) . . ?
F4 P1 F2 90.1(2) . . ?
F4 P1 F5 90.2(3) . . ?
F4 P1 F6 89.5(2) . . ?
C9 N2 Ir1 115.6(3) . . ?
C13 N2 Ir1 126.4(4) . . ?
C13 N2 C9 117.9(5) . . ?
C1 O2 H2 117(5) . . ?
C7 N1 Ir1 125.3(3) . . ?
C8 N1 Ir1 117.3(3) . . ?
C8 N1 C7 117.4(4) . . ?
C6 C7 N1 117.4(4) . . ?
C4 C7 N1 120.5(4) . . ?
C4 C7 C6 122.1(5) . . ?
N1 C8 H8 121.3 . . ?
N1 C8 C9 117.4(4) . . ?
C9 C8 H8 121.3 . . ?
N2 C9 C8 113.4(5) . . ?
N2 C9 C10 122.9(5) . . ?
C10 C9 C8 123.7(5) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 C7 117.9(5) . . ?
C5 C6 H6 121.0 . . ?
C19 C14 Ir1 129.6(4) . . ?
C18 C14 Ir1 69.6(3) . . ?
C18 C14 C19 127.2(4) . . ?
C15 C14 Ir1 71.3(3) . . ?
C15 C14 C19 125.2(4) . . ?
C15 C14 C18 107.3(4) . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
C11 C12 H12 121.3 . . ?
C11 C12 C13 117.5(5) . . ?
C13 C12 H12 121.3 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
C12 C11 H11 119.2 . . ?
C10 C11 C12 121.6(5) . . ?
C10 C11 H11 119.2 . . ?
O1 C1 O2 124.4(5) . . ?
O1 C1 C2 120.0(4) . . ?
O2 C1 C2 115.6(4) . . ?
C7 C4 H4 120.5 . . ?
C7 C4 C3 119.1(5) . . ?
C3 C4 H4 120.5 . . ?
N2 C13 C12 122.7(5) . . ?
N2 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C14 C18 Ir1 71.2(3) . . ?
C14 C18 C23 125.5(4) . . ?
C23 C18 Ir1 126.3(3) . . ?
C17 C18 Ir1 70.7(3) . . ?
C17 C18 C14 108.2(4) . . ?
C17 C18 C23 126.3(4) . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.9(5) . . ?
C2 C3 H3 120.1 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C16 Ir1 129.3(3) . . ?
C17 C16 Ir1 69.9(3) . . ?
C17 C16 C21 127.1(4) . . ?
C15 C16 Ir1 71.2(3) . . ?
C15 C16 C21 125.8(4) . . ?
C15 C16 C17 106.7(4) . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 C5 119.9(4) . . ?
C5 C2 C1 119.1(5) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.3(5) . . ?
C11 C10 H10 121.4 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
C18 C17 Ir1 70.4(3) . . ?
C18 C17 C16 108.0(4) . . ?
C18 C17 C22 126.2(4) . . ?
C16 C17 Ir1 70.8(3) . . ?
C16 C17 C22 125.7(4) . . ?
C22 C17 Ir1 126.2(3) . . ?
C14 C15 Ir1 70.7(3) . . ?
C14 C15 C20 125.6(5) . . ?
C14 C15 C16 109.8(4) . . ?
C20 C15 Ir1 126.4(3) . . ?
C16 C15 Ir1 70.2(3) . . ?
C16 C15 C20 124.6(5) . . ?
C6 C5 C2 121.1(5) . . ?
C6 C5 H5 119.4 . . ?
C2 C5 H5 119.4 . . ?

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
Ir1 N2 C9 C8 -4.1(5) . . . . ?
Ir1 N2 C9 C10 175.1(4) . . . . ?
Ir1 N2 C13 C12 -176.9(4) . . . . ?
Ir1 N1 C7 C6 57.3(6) . . . . ?
Ir1 N1 C7 C4 -123.1(4) . . . . ?
Ir1 N1 C8 C9 1.3(6) . . . . ?
Ir1 C14 C18 C23 121.7(5) . . . . ?
Ir1 C14 C18 C17 -61.4(3) . . . . ?
Ir1 C14 C15 C20 -121.5(5) . . . . ?
Ir1 C14 C15 C16 59.5(3) . . . . ?
Ir1 C18 C17 C16 -61.1(3) . . . . ?
Ir1 C18 C17 C22 121.1(5) . . . . ?
Ir1 C16 C17 C18 60.9(3) . . . . ?
Ir1 C16 C17 C22 -121.3(5) . . . . ?
Ir1 C16 C15 C14 -59.8(4) . . . . ?
Ir1 C16 C15 C20 121.1(5) . . . . ?
O1 C1 C2 C3 -173.2(5) . . . . ?
O1 C1 C2 C5 6.7(7) . . . . ?
N2 C9 C10 C11 0.8(8) . . . . ?
O2 C1 C2 C3 6.1(7) . . . . ?
O2 C1 C2 C5 -173.9(5) . . . . ?
N1 C7 C6 C5 178.8(4) . . . . ?
N1 C7 C4 C3 -179.2(4) . . . . ?
N1 C8 C9 N2 2.0(6) . . . . ?
N1 C8 C9 C10 -177.3(5) . . . . ?
C7 N1 C8 C9 178.6(4) . . . . ?
C7 C6 C5 C2 0.4(8) . . . . ?
C7 C4 C3 C2 0.5(7) . . . . ?
C8 N1 C7 C6 -119.8(5) . . . . ?
C8 N1 C7 C4 59.8(6) . . . . ?
C8 C9 C10 C11 179.9(5) . . . . ?
C9 N2 C13 C12 0.6(7) . . . . ?
C6 C7 C4 C3 0.3(8) . . . . ?
C14 C18 C17 Ir1 61.7(3) . . . . ?
C14 C18 C17 C16 0.6(5) . . . . ?
C14 C18 C17 C22 -177.2(4) . . . . ?
C21 C16 C17 Ir1 124.7(5) . . . . ?
C21 C16 C17 C18 -174.4(5) . . . . ?
C21 C16 C17 C22 3.4(8) . . . . ?
C21 C16 C15 Ir1 -125.5(5) . . . . ?
C21 C16 C15 C14 174.7(5) . . . . ?
C21 C16 C15 C20 -4.3(8) . . . . ?
C12 C11 C10 C9 3.3(8) . . . . ?
C19 C14 C18 Ir1 -124.8(5) . . . . ?
C19 C14 C18 C23 -3.1(8) . . . . ?
C19 C14 C18 C17 173.8(5) . . . . ?
C19 C14 C15 Ir1 125.7(5) . . . . ?
C19 C14 C15 C20 4.2(8) . . . . ?
C19 C14 C15 C16 -174.8(5) . . . . ?
C11 C12 C13 N2 3.2(7) . . . . ?
C1 C2 C5 C6 -179.6(5) . . . . ?
C4 C7 C6 C5 -0.8(8) . . . . ?
C4 C3 C2 C1 179.1(4) . . . . ?
C4 C3 C2 C5 -0.9(7) . . . . ?
C13 N2 C9 C8 178.1(4) . . . . ?
C13 N2 C9 C10 -2.7(7) . . . . ?
C13 C12 C11 C10 -5.2(8) . . . . ?
C18 C14 C15 Ir1 -60.6(3) . . . . ?
C18 C14 C15 C20 178.0(5) . . . . ?
C18 C14 C15 C16 -1.1(6) . . . . ?
C3 C2 C5 C6 0.4(8) . . . . ?
C23 C18 C17 Ir1 -121.4(5) . . . . ?
C23 C18 C17 C16 177.5(4) . . . . ?
C23 C18 C17 C22 -0.3(8) . . . . ?
C17 C16 C15 Ir1 61.2(3) . . . . ?
C17 C16 C15 C14 1.4(6) . . . . ?
C17 C16 C15 C20 -177.6(5) . . . . ?
C15 C14 C18 Ir1 61.7(3) . . . . ?
C15 C14 C18 C23 -176.7(4) . . . . ?
C15 C14 C18 C17 0.3(5) . . . . ?
C15 C16 C17 Ir1 -62.1(3) . . . . ?
C15 C16 C17 C18 -1.2(5) . . . . ?
C15 C16 C17 C22 176.6(4) . . . . ?

_olex2_date_sample_completion    2018-03-09
_olex2_date_sample_data_collection 2018-03-08
_olex2_date_sample_submission    2018-03-08
_olex2_submission_original_sample_id ICP-1
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT973_nov_icp1b           
;
PROBLEM: Check Calcd Positive Resid. Density on       Ir1       2.52 eA-3  
RESPONSE: For strongly diffracting crystals, it is common to see residual Q 
peaks (residual electron density) appearing in the vicinity of heavy atoms.
Ir metal complexes of this nature show residual Q peak heights around
1-3 near the metal.
;
_vrf_PLAT919_nov_icp1b           
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
;
_vrf_PLAT939_nov_icp1b           
;
PROBLEM: Large Value of Not (SHELXL) Weight Optimized S .     135.87 Check
RESPONSE: Since the number of reflections affected by the beam stop was only 1,
we made a choice not to utilize the OMIT instruction.
;
# end Validation Reply Form
