# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2377820'
loop_
_audit_author_name
_audit_author_address
'SATYANARAYAN PAL'
;Utkal University
India
;
_audit_update_record             
;
2024-08-16 deposited with the CCDC.	2025-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H17 F4 Ir N4 O, C H4 O'
_chemical_formula_sum            'C29 H21 F4 Ir N4 O2'
_chemical_formula_weight         725.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   31.3021(7)
_cell_length_b                   10.5130(3)
_cell_length_c                   15.6391(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.530(2)
_cell_angle_gamma                90
_cell_volume                     5146.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9075
_cell_measurement_theta_min      4.4070
_cell_measurement_theta_max      75.6200

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_F_000             2816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    10.619
_shelx_estimated_absorpt_T_min   0.155
_shelx_estimated_absorpt_T_max   0.185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.33867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11983
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.437
_diffrn_reflns_theta_max         72.094
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             5075
_reflns_number_gt                4437
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Wingx version 2021.3 (Farrugia, 2012)'
_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)+(0.0522P)²+12.6522P] 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         4672
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
Ir1 Ir 0.37929(2) 0.25946(2) 0.60832(2) 0.03208(9) Uani 1 1 d . . . . .
F4 F 0.41421(14) 0.7651(3) 0.5961(3) 0.0708(10) Uani 1 1 d . . . . .
N4 N 0.34908(10) 0.0822(3) 0.6291(2) 0.0393(7) Uani 1 1 d . . . . .
N2 N 0.43938(10) 0.1831(3) 0.6196(2) 0.0364(7) Uani 1 1 d . . . . .
F1 F 0.30402(11) 0.3769(4) 0.31694(19) 0.0824(11) Uani 1 1 d . . . . .
N1 N 0.32092(10) 0.3414(4) 0.5865(2) 0.0399(7) Uani 1 1 d . . . . .
F2 F 0.43597(12) 0.1775(4) 0.2870(2) 0.0844(11) Uani 1 1 d . . . . .
O1 O 0.33903(11) 0.0002(3) 0.5702(2) 0.0619(9) Uani 1 1 d . . . . .
F3 F 0.52846(10) 0.4875(3) 0.6285(4) 0.1069(17) Uani 1 1 d . . . . .
N3 N 0.37293(13) 0.2542(3) 0.7431(3) 0.0403(9) Uani 1 1 d . . . . .
C11 C 0.37858(16) 0.2585(3) 0.4801(3) 0.0335(9) Uani 1 1 d . . . . .
C22 C 0.41439(12) 0.4207(4) 0.6052(2) 0.0369(8) Uani 1 1 d . . . . .
C21 C 0.39962(14) 0.5454(4) 0.5991(3) 0.0419(9) Uani 1 1 d . . . . .
H21 H 0.370555 0.561855 0.592928 0.050 Uiso 1 1 calc R U . . .
C5 C 0.30924(13) 0.3567(4) 0.5031(3) 0.0425(9) Uani 1 1 d . . . . .
C17 C 0.45906(13) 0.3996(4) 0.6150(3) 0.0438(10) Uani 1 1 d . . . . .
C27 C 0.35669(13) 0.1431(5) 0.7734(3) 0.0491(11) Uani 1 1 d . . . . .
C10 C 0.41024(15) 0.2124(5) 0.4253(3) 0.0458(10) Uani 1 1 d . . . . .
H10 H 0.434802 0.174836 0.447714 0.055 Uiso 1 1 calc R U . . .
C28 C 0.34428(14) 0.0497(5) 0.7096(3) 0.0514(11) Uani 1 1 d . . . . .
H28 H 0.333443 -0.029356 0.724866 0.062 Uiso 1 1 calc R U . . .
C1 C 0.29352(14) 0.3738(6) 0.6484(3) 0.0551(12) Uani 1 1 d . . . . .
H1 H 0.301872 0.362847 0.705118 0.066 Uiso 1 1 calc R U . . .
C19 C 0.47213(17) 0.6264(5) 0.6115(4) 0.0681(15) Uani 1 1 d . . . . .
H19 H 0.491026 0.694602 0.612817 0.082 Uiso 1 1 calc R U . . .
C18 C 0.48611(17) 0.5031(5) 0.6186(5) 0.0635(15) Uani 1 1 d . . . . .
C26 C 0.35203(17) 0.1218(7) 0.8605(3) 0.0685(16) Uani 1 1 d . . . . .
H26 H 0.342575 0.043369 0.880276 0.082 Uiso 1 1 calc R U . . .
C16 C 0.47237(15) 0.2668(4) 0.6210(4) 0.0448(11) Uani 1 1 d . . . . .
C4 C 0.26890(16) 0.4050(6) 0.4834(4) 0.0644(15) Uani 1 1 d . . . . .
H4 H 0.260607 0.415456 0.426573 0.077 Uiso 1 1 calc R U . . .
C23 C 0.38249(14) 0.3478(5) 0.7994(3) 0.0495(11) Uani 1 1 d . . . . .
H23 H 0.393331 0.424120 0.778804 0.059 Uiso 1 1 calc R U . . .
C12 C 0.44714(14) 0.0585(4) 0.6232(4) 0.0501(11) Uani 1 1 d . . . . .
H12 H 0.424238 0.002239 0.620633 0.060 Uiso 1 1 calc R U . . .
C9 C 0.40478(19) 0.2231(5) 0.3395(4) 0.0530(12) Uani 1 1 d . . . . .
C6 C 0.34160(13) 0.3141(4) 0.4428(3) 0.0410(9) Uani 1 1 d . . . . .
C20 C 0.42859(16) 0.6442(4) 0.6021(3) 0.0513(11) Uani 1 1 d . . . . .
C13 C 0.48779(18) 0.0104(5) 0.6308(5) 0.0716(18) Uani 1 1 d . . . . .
H13 H 0.492372 -0.076731 0.635719 0.086 Uiso 1 1 calc R U . . .
C8 C 0.3695(2) 0.2765(5) 0.3010(3) 0.0568(13) Uani 1 1 d . . . . .
H8 H 0.366614 0.281643 0.241845 0.068 Uiso 1 1 calc R U . . .
C2 C 0.25384(16) 0.4222(7) 0.6311(4) 0.0741(18) Uani 1 1 d . . . . .
H2 H 0.235665 0.444531 0.675407 0.089 Uiso 1 1 calc R U . . .
C3 C 0.24128(17) 0.4373(7) 0.5477(4) 0.0741(18) Uani 1 1 d . . . . .
H3 H 0.214294 0.469227 0.534622 0.089 Uiso 1 1 calc R U . . .
C7 C 0.33884(16) 0.3217(5) 0.3548(3) 0.0525(11) Uani 1 1 d . . . . .
C15 C 0.51385(17) 0.2210(5) 0.6252(6) 0.0710(18) Uani 1 1 d . . . . .
H15 H 0.536703 0.277476 0.624174 0.085 Uiso 1 1 calc R U . . .
C24 C 0.37679(17) 0.3344(7) 0.8855(3) 0.0695(16) Uani 1 1 d . . . . .
H24 H 0.382951 0.401406 0.922411 0.083 Uiso 1 1 calc R U . . .
C14 C 0.52134(17) 0.0936(6) 0.6308(5) 0.083(2) Uani 1 1 d . . . . .
H14 H 0.549213 0.063319 0.634626 0.099 Uiso 1 1 calc R U . . .
C25 C 0.3616(2) 0.2189(8) 0.9176(4) 0.081(2) Uani 1 1 d . . . . .
H25 H 0.358058 0.207373 0.976071 0.097 Uiso 1 1 calc R U . . .
O2 O 0.3062(3) 0.2319(6) 0.1135(7) 0.128(3) Uani 1 1 d . . . . .
H2A H 0.316016 0.161123 0.103508 0.193 Uiso 1 1 calc R U . . .
C29 C 0.2629(4) 0.2219(11) 0.1286(9) 0.129(4) Uani 1 1 d . . . . .
H29A H 0.247420 0.230757 0.075630 0.194 Uiso 1 1 calc R U . . .
H29B H 0.254329 0.287814 0.167332 0.194 Uiso 1 1 calc R U . . .
H29C H 0.256844 0.140371 0.153268 0.194 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 C11 2.005(5) . ?
Ir1 C22 2.021(4) . ?
Ir1 N1 2.046(3) . ?
Ir1 N2 2.051(3) . ?
Ir1 N4 2.116(3) . ?
Ir1 N3 2.119(5) . ?
F4 C20 1.351(5) . ?
N4 O1 1.298(5) . ?
N4 C28 1.314(6) . ?
N2 C12 1.334(6) . ?
N2 C16 1.357(6) . ?
F1 C7 1.365(5) . ?
N1 C1 1.343(6) . ?
N1 C5 1.361(5) . ?
F2 C9 1.368(6) . ?
F3 C18 1.344(6) . ?
N3 C23 1.352(6) . ?
N3 C27 1.361(6) . ?
C11 C10 1.402(6) . ?
C11 C6 1.418(6) . ?
C22 C21 1.393(6) . ?
C22 C17 1.423(6) . ?
C21 C20 1.380(6) . ?
C21 H21 0.9300 . ?
C5 C4 1.393(6) . ?
C5 C6 1.460(6) . ?
C17 C18 1.380(7) . ?
C17 C16 1.460(6) . ?
C27 C26 1.389(7) . ?
C27 C28 1.451(7) . ?
C10 C9 1.356(7) . ?
C10 H10 0.9300 . ?
C28 H28 0.9300 . ?
C1 C2 1.367(7) . ?
C1 H1 0.9300 . ?
C19 C18 1.372(8) . ?
C19 C20 1.382(7) . ?
C19 H19 0.9300 . ?
C26 C25 1.387(10) . ?
C26 H26 0.9300 . ?
C16 C15 1.386(7) . ?
C4 C3 1.375(9) . ?
C4 H4 0.9300 . ?
C23 C24 1.368(7) . ?
C23 H23 0.9300 . ?
C12 C13 1.373(7) . ?
C12 H12 0.9300 . ?
C9 C8 1.373(8) . ?
C6 C7 1.379(6) . ?
C13 C14 1.367(8) . ?
C13 H13 0.9300 . ?
C8 C7 1.368(8) . ?
C8 H8 0.9300 . ?
C2 C3 1.368(9) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C15 C14 1.362(8) . ?
C15 H15 0.9300 . ?
C24 C25 1.398(10) . ?
C24 H24 0.9300 . ?
C14 H14 0.9300 . ?
C25 H25 0.9300 . ?
O2 C29 1.383(13) . ?
O2 H2A 0.8200 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

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
C11 Ir1 C22 88.92(16) . . ?
C11 Ir1 N1 80.41(16) . . ?
C22 Ir1 N1 97.32(15) . . ?
C11 Ir1 N2 94.90(16) . . ?
C22 Ir1 N2 80.33(15) . . ?
N1 Ir1 N2 174.83(13) . . ?
C11 Ir1 N4 98.52(15) . . ?
C22 Ir1 N4 170.46(14) . . ?
N1 Ir1 N4 89.83(14) . . ?
N2 Ir1 N4 93.03(13) . . ?
C11 Ir1 N3 173.71(15) . . ?
C22 Ir1 N3 95.86(15) . . ?
N1 Ir1 N3 94.88(14) . . ?
N2 Ir1 N3 89.95(14) . . ?
N4 Ir1 N3 77.18(13) . . ?
O1 N4 C28 118.5(4) . . ?
O1 N4 Ir1 125.6(3) . . ?
C28 N4 Ir1 115.5(3) . . ?
C12 N2 C16 119.9(4) . . ?
C12 N2 Ir1 123.7(3) . . ?
C16 N2 Ir1 116.4(3) . . ?
C1 N1 C5 119.6(3) . . ?
C1 N1 Ir1 124.2(3) . . ?
C5 N1 Ir1 116.2(3) . . ?
C23 N3 C27 118.6(5) . . ?
C23 N3 Ir1 127.3(3) . . ?
C27 N3 Ir1 114.1(3) . . ?
C10 C11 C6 118.0(4) . . ?
C10 C11 Ir1 127.7(4) . . ?
C6 C11 Ir1 114.3(3) . . ?
C21 C22 C17 118.6(4) . . ?
C21 C22 Ir1 127.7(3) . . ?
C17 C22 Ir1 113.6(3) . . ?
C20 C21 C22 119.2(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
N1 C5 C4 119.3(4) . . ?
N1 C5 C6 113.6(3) . . ?
C4 C5 C6 127.0(4) . . ?
C18 C17 C22 118.9(4) . . ?
C18 C17 C16 125.2(4) . . ?
C22 C17 C16 115.8(4) . . ?
N3 C27 C26 121.6(5) . . ?
N3 C27 C28 116.1(4) . . ?
C26 C27 C28 122.4(5) . . ?
C9 C10 C11 119.5(5) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
N4 C28 C27 116.8(4) . . ?
N4 C28 H28 121.6 . . ?
C27 C28 H28 121.6 . . ?
N1 C1 C2 122.5(5) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C18 C19 C20 116.8(5) . . ?
C18 C19 H19 121.6 . . ?
C20 C19 H19 121.6 . . ?
F3 C18 C19 116.1(5) . . ?
F3 C18 C17 120.8(5) . . ?
C19 C18 C17 123.1(5) . . ?
C25 C26 C27 119.2(6) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
N2 C16 C15 119.2(4) . . ?
N2 C16 C17 113.7(4) . . ?
C15 C16 C17 127.0(5) . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N3 C23 C24 122.4(6) . . ?
N3 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
N2 C12 C13 122.3(4) . . ?
N2 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C10 C9 F2 118.7(5) . . ?
C10 C9 C8 124.2(5) . . ?
F2 C9 C8 117.1(5) . . ?
C7 C6 C11 118.5(4) . . ?
C7 C6 C5 126.1(4) . . ?
C11 C6 C5 115.4(4) . . ?
F4 C20 C21 119.2(4) . . ?
F4 C20 C19 117.6(5) . . ?
C21 C20 C19 123.3(4) . . ?
C14 C13 C12 118.4(5) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C7 C8 C9 116.0(5) . . ?
C7 C8 H8 122.0 . . ?
C9 C8 H8 122.0 . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
F1 C7 C8 116.2(4) . . ?
F1 C7 C6 120.0(4) . . ?
C8 C7 C6 123.8(4) . . ?
C14 C15 C16 120.4(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C23 C24 C25 119.4(6) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C26 C25 C24 118.7(6) . . ?
C26 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
C29 O2 H2A 109.5 . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C17 C22 C21 C20 0.3(6) . . . . ?
Ir1 C22 C21 C20 176.8(3) . . . . ?
C1 N1 C5 C4 -0.3(7) . . . . ?
Ir1 N1 C5 C4 176.3(4) . . . . ?
C1 N1 C5 C6 -178.3(4) . . . . ?
Ir1 N1 C5 C6 -1.6(5) . . . . ?
C21 C22 C17 C18 0.4(7) . . . . ?
Ir1 C22 C17 C18 -176.5(4) . . . . ?
C21 C22 C17 C16 -180.0(4) . . . . ?
Ir1 C22 C17 C16 3.1(5) . . . . ?
C23 N3 C27 C26 -3.6(7) . . . . ?
Ir1 N3 C27 C26 177.4(4) . . . . ?
C23 N3 C27 C28 175.9(4) . . . . ?
Ir1 N3 C27 C28 -3.2(5) . . . . ?
C6 C11 C10 C9 0.4(7) . . . . ?
Ir1 C11 C10 C9 -178.1(4) . . . . ?
O1 N4 C28 C27 178.8(4) . . . . ?
Ir1 N4 C28 C27 5.2(5) . . . . ?
N3 C27 C28 N4 -1.3(6) . . . . ?
C26 C27 C28 N4 178.1(4) . . . . ?
C5 N1 C1 C2 -0.1(9) . . . . ?
Ir1 N1 C1 C2 -176.4(5) . . . . ?
C20 C19 C18 F3 -179.4(6) . . . . ?
C20 C19 C18 C17 1.4(10) . . . . ?
C22 C17 C18 F3 179.5(6) . . . . ?
C16 C17 C18 F3 -0.1(10) . . . . ?
C22 C17 C18 C19 -1.3(10) . . . . ?
C16 C17 C18 C19 179.1(6) . . . . ?
N3 C27 C26 C25 4.1(8) . . . . ?
C28 C27 C26 C25 -175.3(5) . . . . ?
C12 N2 C16 C15 0.8(8) . . . . ?
Ir1 N2 C16 C15 -177.6(5) . . . . ?
C12 N2 C16 C17 179.0(5) . . . . ?
Ir1 N2 C16 C17 0.6(6) . . . . ?
C18 C17 C16 N2 177.2(5) . . . . ?
C22 C17 C16 N2 -2.4(7) . . . . ?
C18 C17 C16 C15 -4.8(10) . . . . ?
C22 C17 C16 C15 175.6(6) . . . . ?
N1 C5 C4 C3 0.2(9) . . . . ?
C6 C5 C4 C3 177.8(6) . . . . ?
C27 N3 C23 C24 0.6(7) . . . . ?
Ir1 N3 C23 C24 179.5(4) . . . . ?
C16 N2 C12 C13 1.7(8) . . . . ?
Ir1 N2 C12 C13 180.0(5) . . . . ?
C11 C10 C9 F2 -179.9(5) . . . . ?
C11 C10 C9 C8 -0.4(9) . . . . ?
C10 C11 C6 C7 -0.8(6) . . . . ?
Ir1 C11 C6 C7 177.9(4) . . . . ?
C10 C11 C6 C5 178.2(4) . . . . ?
Ir1 C11 C6 C5 -3.1(5) . . . . ?
N1 C5 C6 C7 -178.0(5) . . . . ?
C4 C5 C6 C7 4.3(8) . . . . ?
N1 C5 C6 C11 3.1(6) . . . . ?
C4 C5 C6 C11 -174.6(5) . . . . ?
C22 C21 C20 F4 179.9(4) . . . . ?
C22 C21 C20 C19 -0.2(7) . . . . ?
C18 C19 C20 F4 179.2(6) . . . . ?
C18 C19 C20 C21 -0.6(9) . . . . ?
N2 C12 C13 C14 -2.8(11) . . . . ?
C10 C9 C8 C7 0.6(9) . . . . ?
F2 C9 C8 C7 -179.8(5) . . . . ?
N1 C1 C2 C3 0.6(11) . . . . ?
C1 C2 C3 C4 -0.7(11) . . . . ?
C5 C4 C3 C2 0.3(10) . . . . ?
C9 C8 C7 F1 178.9(5) . . . . ?
C9 C8 C7 C6 -1.0(9) . . . . ?
C11 C6 C7 F1 -178.8(4) . . . . ?
C5 C6 C7 F1 2.3(8) . . . . ?
C11 C6 C7 C8 1.2(8) . . . . ?
C5 C6 C7 C8 -177.7(5) . . . . ?
N2 C16 C15 C14 -2.2(11) . . . . ?
C17 C16 C15 C14 179.9(7) . . . . ?
N3 C23 C24 C25 1.8(8) . . . . ?
C16 C15 C14 C13 1.1(13) . . . . ?
C12 C13 C14 C15 1.3(12) . . . . ?
C27 C26 C25 C24 -1.6(9) . . . . ?
C23 C24 C25 C26 -1.2(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 N2 0.93 2.69 3.178(6) 113.5 . yes
C1 H1 N3 0.93 2.57 3.144(6) 120.8 . yes
C4 H4 F1 0.93 2.23 2.851(7) 123.1 . yes
C12 H12 F4 0.93 2.54 3.279(5) 136.4 1_545 yes
C12 H12 N4 0.93 2.50 3.082(5) 120.6 . yes
C15 H15 F3 0.93 2.22 2.839(7) 123.0 . yes
O2 H2A O1 0.82 1.92 2.734(8) 175.2 6 yes
C10 H10 N2 0.93 2.69 3.178(6) 113.5 . yes
C1 H1 N3 0.93 2.57 3.144(6) 120.8 . yes
C4 H4 F1 0.93 2.23 2.851(7) 123.1 . yes
C12 H12 F4 0.93 2.54 3.279(5) 136.4 1_545 yes
C12 H12 N4 0.93 2.50 3.082(5) 120.6 . yes
C15 H15 F3 0.93 2.22 2.839(7) 123.0 . yes
O2 H2A O1 0.82 1.92 2.734(8) 175.2 6 yes

_refine_diff_density_max         1.036
_refine_diff_density_min         -1.382
_refine_diff_density_rms         0.137

####################################################################### 
# 
# 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 2377821'
loop_
_audit_author_name
_audit_author_address
'SATYANARAYAN PAL'
;Utkal University
India
;
_audit_update_record             
;
2024-08-16 deposited with the CCDC.	2025-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H20 F4 Ir N5 O'
_chemical_formula_sum            'C33 H20 F4 Ir N5 O'
_chemical_formula_weight         770.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   32.8730(12)
_cell_length_b                   10.6210(4)
_cell_length_c                   15.9665(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.9220(10)
_cell_angle_gamma                90
_cell_volume                     5561.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9783
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      32.49

_exptl_crystal_description       rectangular
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_F_000             2992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    4.866
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.189
_exptl_absorpt_correction_T_max  0.657
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41429
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.674
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4846
_reflns_number_gt                3935
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2019/3 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEP 3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_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)+16.8286P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         4846
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0414
_refine_ls_wR_factor_gt          0.0393
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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 0.11547(2) 0.25040(2) 0.42261(2) 0.02849(5) Uani 1 1 d . . . . .
F2 F 0.07875(7) -0.2483(2) 0.43878(17) 0.0681(6) Uani 1 1 d . . . . .
F3 F 0.04993(8) 0.2964(3) 0.72306(16) 0.0809(9) Uani 1 1 d . . . . .
F4 F 0.17236(9) 0.0769(3) 0.71521(16) 0.0810(9) Uani 1 1 d . . . . .
F1 F -0.02753(8) 0.0301(3) 0.3679(3) 0.0995(12) Uani 1 1 d . . . . .
O1 O 0.15833(8) 0.4802(2) 0.48884(15) 0.0454(6) Uani 1 1 d . . . . .
N5 N 0.21675(11) 0.5609(4) 0.2944(2) 0.0604(10) Uani 1 1 d . . . . .
N3 N 0.12574(8) 0.2735(3) 0.29374(16) 0.0334(6) Uani 1 1 d . . . . .
N4 N 0.14743(8) 0.4199(3) 0.42078(17) 0.0338(6) Uani 1 1 d . . . . .
C30 C 0.17771(14) 0.6809(4) 0.3861(3) 0.0640(12) Uani 1 1 d . . . . .
H30 H 0.154789 0.686090 0.417019 0.077 Uiso 1 1 calc R U . . .
C31 C 0.20469(18) 0.7806(5) 0.3861(4) 0.0888(18) Uani 1 1 d . . . . .
H31 H 0.200648 0.853298 0.416861 0.107 Uiso 1 1 calc R U . . .
C8 C 0.02550(13) -0.1099(4) 0.4030(3) 0.0600(12) Uani 1 1 d . . . . .
H8 H 0.007282 -0.176940 0.399218 0.072 Uiso 1 1 calc R U . . .
C9 C 0.06585(13) -0.1276(4) 0.4236(2) 0.0473(9) Uani 1 1 d . . . . .
C27 C 0.14490(10) 0.3833(4) 0.2752(2) 0.0392(8) Uani 1 1 d . . . . .
C21 C 0.07990(11) 0.2795(3) 0.5943(2) 0.0414(9) Uani 1 1 d . . . . .
H21 H 0.058314 0.324936 0.568512 0.050 Uiso 1 1 calc R U . . .
C33 C 0.24264(16) 0.6594(6) 0.2956(3) 0.0799(16) Uani 1 1 d . . . . .
H33 H 0.265493 0.652436 0.264603 0.096 Uiso 1 1 calc R U . . .
C2 C 0.01442(14) 0.5002(4) 0.3736(4) 0.0678(14) Uani 1 1 d . . . . .
H2 H 0.010663 0.586865 0.369774 0.081 Uiso 1 1 calc R U . . .
C16 C 0.17791(10) 0.1386(3) 0.5378(2) 0.0371(8) Uani 1 1 d . . . . .
C7 C 0.01284(13) 0.0120(4) 0.3881(3) 0.0585(12) Uani 1 1 d . . . . .
C17 C 0.14438(11) 0.1721(3) 0.5894(2) 0.0386(8) Uani 1 1 d . . . . .
C32 C 0.23780(19) 0.7675(6) 0.3385(4) 0.0950(19) Uani 1 1 d . . . . .
H32 H 0.256663 0.832460 0.335912 0.114 Uiso 1 1 calc R U . . .
C6 C 0.03914(11) 0.1141(4) 0.3948(2) 0.0415(8) Uani 1 1 d . . . . .
C28 C 0.15823(10) 0.4604(3) 0.3466(2) 0.0369(8) Uani 1 1 d . . . . .
C10 C 0.09370(11) -0.0327(3) 0.4295(2) 0.0390(8) Uani 1 1 d . . . . .
H10 H 0.121055 -0.050517 0.443173 0.047 Uiso 1 1 calc R U . . .
C24 C 0.11934(13) 0.2181(5) 0.1490(2) 0.0586(12) Uani 1 1 d . . . . .
H24 H 0.111406 0.160186 0.107322 0.070 Uiso 1 1 calc R U . . .
C23 C 0.11368(11) 0.1937(4) 0.2312(2) 0.0440(9) Uani 1 1 d . . . . .
H23 H 0.100981 0.118852 0.244760 0.053 Uiso 1 1 calc R U . . .
C12 C 0.19901(11) 0.1462(4) 0.4013(2) 0.0447(9) Uani 1 1 d . . . . .
H12 H 0.193356 0.165841 0.344921 0.054 Uiso 1 1 calc R U . . .
C29 C 0.18468(11) 0.5730(4) 0.3403(2) 0.0442(9) Uani 1 1 d . . . . .
C15 C 0.21561(12) 0.0886(4) 0.5649(3) 0.0515(10) Uani 1 1 d . . . . .
H15 H 0.221173 0.068857 0.621270 0.062 Uiso 1 1 calc R U . . .
C26 C 0.14969(13) 0.4136(4) 0.1913(2) 0.0537(11) Uani 1 1 d . . . . .
H26 H 0.161415 0.490071 0.177912 0.064 Uiso 1 1 calc R U . . .
C13 C 0.23667(12) 0.0975(4) 0.4263(3) 0.0513(10) Uani 1 1 d . . . . .
H13 H 0.256223 0.084779 0.387686 0.062 Uiso 1 1 calc R U . . .
C1 C 0.05214(12) 0.4518(4) 0.3920(3) 0.0496(10) Uani 1 1 d . . . . .
H1 H 0.074013 0.506822 0.401013 0.059 Uiso 1 1 calc R U . . .
C19 C 0.11133(14) 0.1879(5) 0.7204(3) 0.0610(12) Uani 1 1 d . . . . .
H19 H 0.110890 0.171098 0.777531 0.073 Uiso 1 1 calc R U . . .
C14 C 0.24465(13) 0.0683(4) 0.5086(3) 0.0581(12) Uani 1 1 d . . . . .
H14 H 0.269825 0.034531 0.526760 0.070 Uiso 1 1 calc R U . . .
C18 C 0.14266(13) 0.1469(4) 0.6742(2) 0.0517(10) Uani 1 1 d . . . . .
C4 C -0.01178(13) 0.2935(4) 0.3667(4) 0.0685(14) Uani 1 1 d . . . . .
H4 H -0.033683 0.238358 0.358619 0.082 Uiso 1 1 calc R U . . .
C3 C -0.01810(14) 0.4202(5) 0.3605(4) 0.0795(17) Uani 1 1 d . . . . .
H3 H -0.044147 0.451923 0.347647 0.095 Uiso 1 1 calc R U . . .
C25 C 0.13722(15) 0.3316(5) 0.1290(3) 0.0652(13) Uani 1 1 d . . . . .
H25 H 0.140707 0.351649 0.073285 0.078 Uiso 1 1 calc R U . . .
C11 C 0.08117(10) 0.0913(3) 0.4151(2) 0.0320(7) Uani 1 1 d . . . . .
C5 C 0.02735(10) 0.2464(4) 0.3850(2) 0.0422(8) Uani 1 1 d . . . . .
C20 C 0.08113(12) 0.2541(5) 0.6782(2) 0.0529(9) Uani 1 1 d . . . . .
N2 N 0.17015(8) 0.1665(3) 0.45514(17) 0.0327(6) Uani 1 1 d . . . . .
C22 C 0.11153(9) 0.2365(3) 0.54756(19) 0.0320(7) Uani 1 1 d . . . . .
N1 N 0.05910(8) 0.3276(3) 0.39777(18) 0.0350(6) 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 C22 2.014(3) . ?
Ir1 C11 2.030(3) . ?
Ir1 N1 2.041(3) . ?
Ir1 N2 2.041(3) . ?
Ir1 N4 2.086(3) . ?
Ir1 N3 2.122(3) . ?
F2 C9 1.366(5) . ?
F3 C20 1.367(4) . ?
F4 C18 1.359(5) . ?
F1 C7 1.358(5) . ?
O1 N4 1.291(4) . ?
N5 C29 1.330(5) . ?
N5 C33 1.348(6) . ?
N3 C23 1.348(5) . ?
N3 C27 1.368(4) . ?
N4 C28 1.331(4) . ?
C30 C31 1.381(6) . ?
C30 C29 1.387(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.376(8) . ?
C31 H31 0.9300 . ?
C8 C9 1.358(6) . ?
C8 C7 1.375(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.361(5) . ?
C27 C26 1.397(5) . ?
C27 C28 1.447(5) . ?
C21 C20 1.365(5) . ?
C21 C22 1.397(5) . ?
C21 H21 0.9300 . ?
C33 C32 1.353(8) . ?
C33 H33 0.9300 . ?
C2 C1 1.356(6) . ?
C2 C3 1.370(7) . ?
C2 H2 0.9300 . ?
C16 N2 1.359(4) . ?
C16 C15 1.390(5) . ?
C16 C17 1.465(5) . ?
C7 C6 1.387(6) . ?
C17 C18 1.385(5) . ?
C17 C22 1.408(5) . ?
C32 H32 0.9300 . ?
C6 C11 1.418(5) . ?
C6 C5 1.463(6) . ?
C28 C29 1.486(5) . ?
C10 C11 1.395(5) . ?
C10 H10 0.9300 . ?
C24 C23 1.364(5) . ?
C24 C25 1.387(7) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C12 N2 1.341(4) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C15 C14 1.373(6) . ?
C15 H15 0.9300 . ?
C26 C25 1.364(6) . ?
C26 H26 0.9300 . ?
C13 C14 1.358(6) . ?
C13 H13 0.9300 . ?
C1 N1 1.340(5) . ?
C1 H1 0.9300 . ?
C19 C20 1.358(6) . ?
C19 C18 1.378(6) . ?
C19 H19 0.9300 . ?
C14 H14 0.9300 . ?
C4 C3 1.365(7) . ?
C4 C5 1.392(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C25 H25 0.9300 . ?
C5 N1 1.359(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
C22 Ir1 C11 85.64(13) . . ?
C22 Ir1 N1 95.91(12) . . ?
C11 Ir1 N1 80.20(12) . . ?
C22 Ir1 N2 80.27(12) . . ?
C11 Ir1 N2 97.32(12) . . ?
N1 Ir1 N2 175.63(11) . . ?
C22 Ir1 N4 98.27(12) . . ?
C11 Ir1 N4 174.73(12) . . ?
N1 Ir1 N4 95.84(11) . . ?
N2 Ir1 N4 86.85(11) . . ?
C22 Ir1 N3 174.02(11) . . ?
C11 Ir1 N3 99.41(12) . . ?
N1 Ir1 N3 88.15(10) . . ?
N2 Ir1 N3 95.82(10) . . ?
N4 Ir1 N3 76.89(11) . . ?
C29 N5 C33 116.2(4) . . ?
C23 N3 C27 119.5(3) . . ?
C23 N3 Ir1 126.0(2) . . ?
C27 N3 Ir1 114.5(2) . . ?
O1 N4 C28 120.9(3) . . ?
O1 N4 Ir1 121.8(2) . . ?
C28 N4 Ir1 117.2(2) . . ?
C31 C30 C29 120.2(4) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C32 C31 C30 117.1(5) . . ?
C32 C31 H31 121.5 . . ?
C30 C31 H31 121.5 . . ?
C9 C8 C7 116.9(4) . . ?
C9 C8 H8 121.6 . . ?
C7 C8 H8 121.6 . . ?
C8 C9 C10 123.8(4) . . ?
C8 C9 F2 117.3(4) . . ?
C10 C9 F2 118.9(4) . . ?
N3 C27 C26 119.2(4) . . ?
N3 C27 C28 115.6(3) . . ?
C26 C27 C28 125.2(4) . . ?
C20 C21 C22 119.1(3) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
N5 C33 C32 124.7(5) . . ?
N5 C33 H33 117.6 . . ?
C32 C33 H33 117.6 . . ?
C1 C2 C3 119.4(4) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N2 C16 C15 119.3(3) . . ?
N2 C16 C17 113.3(3) . . ?
C15 C16 C17 127.4(3) . . ?
F1 C7 C8 117.0(4) . . ?
F1 C7 C6 120.1(4) . . ?
C8 C7 C6 122.9(4) . . ?
C18 C17 C22 118.5(3) . . ?
C18 C17 C16 125.9(3) . . ?
C22 C17 C16 115.7(3) . . ?
C33 C32 C31 119.3(5) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C7 C6 C11 118.5(4) . . ?
C7 C6 C5 125.7(3) . . ?
C11 C6 C5 115.8(3) . . ?
N4 C28 C27 115.6(3) . . ?
N4 C28 C29 120.9(3) . . ?
C27 C28 C29 123.3(3) . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C23 C24 C25 118.3(4) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
N3 C23 C24 122.7(4) . . ?
N3 C23 H23 118.6 . . ?
C24 C23 H23 118.6 . . ?
N2 C12 C13 122.5(4) . . ?
N2 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
N5 C29 C30 122.4(4) . . ?
N5 C29 C28 116.7(4) . . ?
C30 C29 C28 120.7(3) . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C25 C26 C27 120.3(4) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C14 C13 C12 118.5(4) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
N1 C1 C2 122.5(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C20 C19 C18 116.4(4) . . ?
C20 C19 H19 121.8 . . ?
C18 C19 H19 121.8 . . ?
C13 C14 C15 120.1(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
F4 C18 C19 117.0(4) . . ?
F4 C18 C17 120.0(4) . . ?
C19 C18 C17 123.0(4) . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C26 C25 C24 119.9(4) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C10 C11 C6 118.1(3) . . ?
C10 C11 Ir1 128.3(3) . . ?
C6 C11 Ir1 113.6(2) . . ?
N1 C5 C4 119.5(4) . . ?
N1 C5 C6 113.5(3) . . ?
C4 C5 C6 127.0(4) . . ?
C19 C20 C21 124.2(4) . . ?
C19 C20 F3 117.3(3) . . ?
C21 C20 F3 118.5(4) . . ?
C12 N2 C16 119.6(3) . . ?
C12 N2 Ir1 123.8(2) . . ?
C16 N2 Ir1 116.5(2) . . ?
C21 C22 C17 118.7(3) . . ?
C21 C22 Ir1 127.2(3) . . ?
C17 C22 Ir1 114.0(2) . . ?
C1 N1 C5 119.2(3) . . ?
C1 N1 Ir1 123.9(3) . . ?
C5 N1 Ir1 116.9(2) . . ?

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
C29 C30 C31 C32 0.6(8) . . . . ?
C7 C8 C9 C10 -0.4(7) . . . . ?
C7 C8 C9 F2 179.8(4) . . . . ?
C23 N3 C27 C26 3.3(5) . . . . ?
Ir1 N3 C27 C26 -174.0(3) . . . . ?
C23 N3 C27 C28 -177.5(3) . . . . ?
Ir1 N3 C27 C28 5.2(4) . . . . ?
C29 N5 C33 C32 -0.9(8) . . . . ?
C9 C8 C7 F1 -179.7(4) . . . . ?
C9 C8 C7 C6 -1.2(7) . . . . ?
N2 C16 C17 C18 175.4(4) . . . . ?
C15 C16 C17 C18 -7.6(6) . . . . ?
N2 C16 C17 C22 -5.1(5) . . . . ?
C15 C16 C17 C22 171.9(4) . . . . ?
N5 C33 C32 C31 1.0(10) . . . . ?
C30 C31 C32 C33 -0.8(9) . . . . ?
F1 C7 C6 C11 -179.3(4) . . . . ?
C8 C7 C6 C11 2.2(7) . . . . ?
F1 C7 C6 C5 2.6(7) . . . . ?
C8 C7 C6 C5 -175.9(4) . . . . ?
O1 N4 C28 C27 178.7(3) . . . . ?
Ir1 N4 C28 C27 2.4(4) . . . . ?
O1 N4 C28 C29 2.7(5) . . . . ?
Ir1 N4 C28 C29 -173.7(3) . . . . ?
N3 C27 C28 N4 -5.0(5) . . . . ?
C26 C27 C28 N4 174.1(4) . . . . ?
N3 C27 C28 C29 170.9(3) . . . . ?
C26 C27 C28 C29 -10.0(6) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
F2 C9 C10 C11 -179.4(3) . . . . ?
C27 N3 C23 C24 -0.8(5) . . . . ?
Ir1 N3 C23 C24 176.2(3) . . . . ?
C25 C24 C23 N3 -1.9(6) . . . . ?
C33 N5 C29 C30 0.7(6) . . . . ?
C33 N5 C29 C28 -173.9(4) . . . . ?
C31 C30 C29 N5 -0.6(7) . . . . ?
C31 C30 C29 C28 173.8(4) . . . . ?
N4 C28 C29 N5 130.5(4) . . . . ?
C27 C28 C29 N5 -45.2(5) . . . . ?
N4 C28 C29 C30 -44.3(5) . . . . ?
C27 C28 C29 C30 140.1(4) . . . . ?
N2 C16 C15 C14 0.2(6) . . . . ?
C17 C16 C15 C14 -176.6(4) . . . . ?
N3 C27 C26 C25 -3.3(6) . . . . ?
C28 C27 C26 C25 177.6(4) . . . . ?
N2 C12 C13 C14 0.4(6) . . . . ?
C3 C2 C1 N1 0.3(8) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C16 C15 C14 C13 0.3(7) . . . . ?
C20 C19 C18 F4 -177.8(4) . . . . ?
C20 C19 C18 C17 0.9(7) . . . . ?
C22 C17 C18 F4 175.1(4) . . . . ?
C16 C17 C18 F4 -5.4(6) . . . . ?
C22 C17 C18 C19 -3.6(6) . . . . ?
C16 C17 C18 C19 175.9(4) . . . . ?
C5 C4 C3 C2 -0.7(9) . . . . ?
C1 C2 C3 C4 0.2(9) . . . . ?
C27 C26 C25 C24 0.7(7) . . . . ?
C23 C24 C25 C26 1.9(7) . . . . ?
C9 C10 C11 C6 0.2(5) . . . . ?
C9 C10 C11 Ir1 178.2(3) . . . . ?
C7 C6 C11 C10 -1.6(5) . . . . ?
C5 C6 C11 C10 176.6(3) . . . . ?
C7 C6 C11 Ir1 -179.9(3) . . . . ?
C5 C6 C11 Ir1 -1.7(4) . . . . ?
C3 C4 C5 N1 0.8(7) . . . . ?
C3 C4 C5 C6 179.2(5) . . . . ?
C7 C6 C5 N1 177.7(4) . . . . ?
C11 C6 C5 N1 -0.4(5) . . . . ?
C7 C6 C5 C4 -0.7(7) . . . . ?
C11 C6 C5 C4 -178.9(4) . . . . ?
C18 C19 C20 C21 1.2(7) . . . . ?
C18 C19 C20 F3 -179.5(4) . . . . ?
C22 C21 C20 C19 -0.4(7) . . . . ?
C22 C21 C20 F3 -179.8(4) . . . . ?
C13 C12 N2 C16 0.1(6) . . . . ?
C13 C12 N2 Ir1 175.3(3) . . . . ?
C15 C16 N2 C12 -0.4(5) . . . . ?
C17 C16 N2 C12 176.9(3) . . . . ?
C15 C16 N2 Ir1 -176.0(3) . . . . ?
C17 C16 N2 Ir1 1.3(4) . . . . ?
C20 C21 C22 C17 -2.3(5) . . . . ?
C20 C21 C22 Ir1 175.5(3) . . . . ?
C18 C17 C22 C21 4.2(5) . . . . ?
C16 C17 C22 C21 -175.3(3) . . . . ?
C18 C17 C22 Ir1 -173.9(3) . . . . ?
C16 C17 C22 Ir1 6.5(4) . . . . ?
C2 C1 N1 C5 -0.2(6) . . . . ?
C2 C1 N1 Ir1 178.5(4) . . . . ?
C4 C5 N1 C1 -0.3(6) . . . . ?
C6 C5 N1 C1 -178.9(3) . . . . ?
C4 C5 N1 Ir1 -179.1(3) . . . . ?
C6 C5 N1 Ir1 2.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C30 H30 F2 0.93 2.64 3.497(5) 153.4 1_565 yes
C12 H12 N3 0.93 2.58 3.164(5) 121.1 . yes
C15 H15 F4 0.93 2.27 2.875(5) 122.0 . yes
C26 H26 N5 0.93 2.62 3.085(6) 111.4 . yes
C1 H1 N4 0.93 2.58 3.153(5) 120.0 . yes
C4 H4 F1 0.93 2.22 2.845(5) 123.4 . yes
C30 H30 F2 0.93 2.64 3.497(5) 153.4 1_565 yes
C12 H12 N3 0.93 2.58 3.164(5) 121.1 . yes
C15 H15 F4 0.93 2.27 2.875(5) 122.0 . yes
C26 H26 N5 0.93 2.62 3.085(6) 111.4 . yes
C1 H1 N4 0.93 2.58 3.153(5) 120.0 . yes
C4 H4 F1 0.93 2.22 2.845(5) 123.4 . yes

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.061

