# 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_aaa
_database_code_depnum_ccdc_archive 'CCDC 1980050'
loop_
_audit_author_name
_audit_author_address
a-d
;Yulin Normal University
China
;
_audit_update_record             
;
2020-01-27 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C31 H21 F Ir N3 O'
_chemical_formula_sum            'C31 H21 F Ir N3 O'
_chemical_formula_weight         662.71
_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'
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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.4485(7)
_cell_length_b                   9.3218(6)
_cell_length_c                   23.3115(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.268(2)
_cell_angle_gamma                90
_cell_volume                     2485.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.973
_shelx_estimated_absorpt_T_max   0.645
_shelx_estimated_absorpt_T_min   0.219
_exptl_absorpt_coefficient_mu    5.409
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1502 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.5406.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.089
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38204
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.930
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4666
_reflns_number_total             5704
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.803
_refine_diff_density_min         -1.413
_refine_diff_density_rms         0.281
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5704
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+0.1620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0796
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C29(H29), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.27128(2) 0.73745(2) 0.08223(2) 0.03453(7) Uani 1 1 d . . . . .
F1 F 0.1192(3) 1.0040(4) -0.17038(11) 0.0908(10) Uani 1 1 d . . . . .
O1 O 0.3765(2) 0.8521(3) 0.02340(10) 0.0385(6) Uani 1 1 d . . . . .
N1 N 0.2450(3) 0.9129(3) 0.13185(12) 0.0358(7) Uani 1 1 d . . . . .
N2 N 0.1438(3) 0.8068(3) 0.01910(13) 0.0332(7) Uani 1 1 d . . . . .
N3 N 0.3053(3) 0.5518(3) 0.03967(14) 0.0454(8) Uani 1 1 d . . . . .
C1 C 0.2964(3) 1.0398(4) 0.12448(17) 0.0419(9) Uani 1 1 d . . . . .
H1 H 0.3444 1.0518 0.0936 0.050 Uiso 1 1 calc R . . . .
C2 C 0.2807(3) 1.1531(5) 0.16082(19) 0.0515(11) Uani 1 1 d . . . . .
H2 H 0.3170 1.2407 0.1546 0.062 Uiso 1 1 calc R . . . .
C3 C 0.2098(4) 1.1342(5) 0.20694(18) 0.0540(11) Uani 1 1 d . . . . .
H3 H 0.1990 1.2089 0.2327 0.065 Uiso 1 1 calc R . . . .
C4 C 0.1560(4) 1.0060(5) 0.21441(17) 0.0499(10) Uani 1 1 d . . . . .
H4 H 0.1080 0.9936 0.2453 0.060 Uiso 1 1 calc R . . . .
C5 C 0.1717(3) 0.8937(4) 0.17666(15) 0.0385(9) Uani 1 1 d . . . . .
C6 C 0.1181(4) 0.7510(4) 0.17777(18) 0.0419(10) Uani 1 1 d . . . . .
C7 C 0.0326(4) 0.7124(5) 0.2152(2) 0.0557(12) Uani 1 1 d . . . . .
H7 H 0.0063 0.7786 0.2416 0.067 Uiso 1 1 calc R . . . .
C8 C -0.0128(4) 0.5774(6) 0.2134(2) 0.0695(14) Uani 1 1 d . . . . .
H8 H -0.0697 0.5518 0.2389 0.083 Uiso 1 1 calc R . . . .
C9 C 0.0243(5) 0.4783(6) 0.1743(2) 0.0750(15) Uani 1 1 d . . . . .
H9 H -0.0079 0.3867 0.1730 0.090 Uiso 1 1 calc R . . . .
C10 C 0.1100(4) 0.5165(5) 0.1368(2) 0.0590(12) Uani 1 1 d . . . . .
H10 H 0.1361 0.4485 0.1110 0.071 Uiso 1 1 calc R . . . .
C11 C 0.1584(3) 0.6538(4) 0.13656(16) 0.0396(9) Uani 1 1 d . . . . .
C12 C 0.4092(3) 0.6672(4) 0.13071(17) 0.0431(10) Uani 1 1 d . . . . .
C13 C 0.4680(4) 0.7367(5) 0.1769(2) 0.0570(14) Uani 1 1 d . . . . .
H13 H 0.4405 0.8246 0.1896 0.068 Uiso 1 1 calc R . . . .
C14 C 0.5664(4) 0.6764(7) 0.2039(2) 0.0725(15) Uani 1 1 d . . . . .
H14 H 0.6052 0.7254 0.2338 0.087 Uiso 1 1 calc R . . . .
C15 C 0.6067(5) 0.5454(8) 0.1870(3) 0.086(2) Uani 1 1 d . . . . .
H15 H 0.6711 0.5045 0.2062 0.103 Uiso 1 1 calc R . . . .
C16 C 0.5522(4) 0.4739(6) 0.1416(2) 0.0733(16) Uani 1 1 d . . . . .
H16 H 0.5805 0.3854 0.1300 0.088 Uiso 1 1 calc R . . . .
C17 C 0.4539(4) 0.5350(5) 0.1128(2) 0.0533(11) Uani 1 1 d . . . . .
C18 C 0.3967(4) 0.4729(4) 0.0625(2) 0.0547(12) Uani 1 1 d . . . . .
C19 C 0.4297(5) 0.3498(5) 0.0343(3) 0.0704(15) Uani 1 1 d . . . . .
H19 H 0.4927 0.2966 0.0490 0.084 Uiso 1 1 calc R . . . .
C20 C 0.3726(6) 0.3049(6) -0.0142(3) 0.0812(19) Uani 1 1 d . . . . .
H20 H 0.3968 0.2221 -0.0326 0.097 Uiso 1 1 calc R . . . .
C21 C 0.2779(5) 0.3819(5) -0.0366(2) 0.0728(16) Uani 1 1 d . . . . .
H21 H 0.2365 0.3514 -0.0695 0.087 Uiso 1 1 calc R . . . .
C22 C 0.2475(4) 0.5055(5) -0.0084(2) 0.0566(12) Uani 1 1 d . . . . .
H22 H 0.1846 0.5591 -0.0230 0.068 Uiso 1 1 calc R . . . .
C23 C 0.0291(4) 0.7858(4) 0.01798(19) 0.0429(9) Uani 1 1 d . . . . .
H23 H -0.0044 0.7458 0.0500 0.051 Uiso 1 1 calc R . . . .
C24 C -0.0434(4) 0.8215(5) -0.02970(19) 0.0515(11) Uani 1 1 d . . . . .
H24 H -0.1235 0.8056 -0.0289 0.062 Uiso 1 1 calc R . . . .
C25 C 0.0032(4) 0.8791(5) -0.07671(19) 0.0521(11) Uani 1 1 d . . . . .
H25 H -0.0443 0.9009 -0.1088 0.062 Uiso 1 1 calc R . . . .
C26 C 0.1254(3) 0.9062(4) -0.07674(16) 0.0422(9) Uani 1 1 d . . . . .
C27 C 0.1926(3) 0.8679(4) -0.02756(15) 0.0336(8) Uani 1 1 d . . . . .
C28 C 0.3165(3) 0.8902(4) -0.02301(15) 0.0343(8) Uani 1 1 d . . . . .
C29 C 0.3675(4) 0.9545(4) -0.07024(17) 0.0444(10) Uani 1 1 d . . . . .
H29 H 0.4475 0.9723 -0.0689 0.053 Uiso 1 1 calc R . . . .
C30 C 0.3006(4) 0.9924(5) -0.11941(17) 0.0556(11) Uani 1 1 d . . . . .
H30 H 0.3364 1.0341 -0.1504 0.067 Uiso 1 1 calc R . . . .
C31 C 0.1831(4) 0.9684(5) -0.12196(17) 0.0531(11) 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 O1 2.146(2) . ?
Ir1 N1 2.033(3) . ?
Ir1 N2 2.132(3) . ?
Ir1 N3 2.040(3) . ?
Ir1 C11 2.003(4) . ?
Ir1 C12 2.015(4) . ?
F1 C31 1.362(5) . ?
O1 C28 1.307(4) . ?
N1 C1 1.335(5) . ?
N1 C5 1.378(5) . ?
N2 C23 1.327(5) . ?
N2 C27 1.367(4) . ?
N3 C18 1.368(5) . ?
N3 C22 1.349(5) . ?
C1 C2 1.370(5) . ?
C2 C3 1.384(6) . ?
C3 C4 1.359(6) . ?
C4 C5 1.384(5) . ?
C5 C6 1.465(5) . ?
C6 C7 1.385(6) . ?
C6 C11 1.411(6) . ?
C7 C8 1.362(7) . ?
C8 C9 1.377(7) . ?
C9 C10 1.387(6) . ?
C10 C11 1.395(5) . ?
C12 C13 1.405(6) . ?
C12 C17 1.404(6) . ?
C13 C14 1.387(6) . ?
C14 C15 1.369(8) . ?
C15 C16 1.379(8) . ?
C16 C17 1.408(6) . ?
C17 C18 1.441(6) . ?
C18 C19 1.383(6) . ?
C19 C20 1.350(8) . ?
C20 C21 1.385(8) . ?
C21 C22 1.379(6) . ?
C23 C24 1.401(6) . ?
C24 C25 1.349(6) . ?
C25 C26 1.422(5) . ?
C26 C27 1.401(5) . ?
C26 C31 1.392(5) . ?
C27 C28 1.434(5) . ?
C28 C29 1.401(5) . ?
C29 C30 1.398(5) . ?
C30 C31 1.363(6) . ?

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
N1 Ir1 O1 93.56(11) . . ?
N1 Ir1 N2 92.06(11) . . ?
N1 Ir1 N3 174.17(12) . . ?
N2 Ir1 O1 78.12(10) . . ?
N3 Ir1 O1 89.37(10) . . ?
N3 Ir1 N2 93.47(13) . . ?
C11 Ir1 O1 172.11(12) . . ?
C11 Ir1 N1 80.78(14) . . ?
C11 Ir1 N2 96.50(13) . . ?
C11 Ir1 N3 96.77(14) . . ?
C11 Ir1 C12 91.72(15) . . ?
C12 Ir1 O1 94.18(12) . . ?
C12 Ir1 N1 94.16(15) . . ?
C12 Ir1 N2 170.40(13) . . ?
C12 Ir1 N3 80.59(16) . . ?
C28 O1 Ir1 112.0(2) . . ?
C1 N1 Ir1 124.3(3) . . ?
C1 N1 C5 119.8(3) . . ?
C5 N1 Ir1 115.8(3) . . ?
C23 N2 Ir1 128.2(3) . . ?
C23 N2 C27 118.8(3) . . ?
C27 N2 Ir1 112.7(2) . . ?
C18 N3 Ir1 115.1(3) . . ?
C22 N3 Ir1 125.3(3) . . ?
C22 N3 C18 119.5(4) . . ?
N1 C1 C2 122.3(4) . . ?
C1 C2 C3 118.6(4) . . ?
C4 C3 C2 119.6(4) . . ?
C3 C4 C5 120.9(4) . . ?
N1 C5 C4 118.8(4) . . ?
N1 C5 C6 113.5(3) . . ?
C4 C5 C6 127.6(4) . . ?
C7 C6 C5 123.6(4) . . ?
C7 C6 C11 121.4(4) . . ?
C11 C6 C5 115.0(4) . . ?
C8 C7 C6 120.0(4) . . ?
C7 C8 C9 120.8(4) . . ?
C8 C9 C10 119.4(5) . . ?
C9 C10 C11 121.9(4) . . ?
C6 C11 Ir1 114.6(3) . . ?
C10 C11 Ir1 128.7(3) . . ?
C10 C11 C6 116.5(4) . . ?
C13 C12 Ir1 128.4(3) . . ?
C17 C12 Ir1 113.9(3) . . ?
C17 C12 C13 117.6(4) . . ?
C14 C13 C12 121.1(5) . . ?
C15 C14 C13 120.4(6) . . ?
C14 C15 C16 120.4(5) . . ?
C15 C16 C17 120.0(5) . . ?
C12 C17 C16 120.4(5) . . ?
C12 C17 C18 115.8(4) . . ?
C16 C17 C18 123.7(4) . . ?
N3 C18 C17 114.6(4) . . ?
N3 C18 C19 118.7(5) . . ?
C19 C18 C17 126.6(5) . . ?
C20 C19 C18 121.5(5) . . ?
C19 C20 C21 120.1(5) . . ?
C22 C21 C20 117.5(5) . . ?
N3 C22 C21 122.6(5) . . ?
N2 C23 C24 122.3(4) . . ?
C25 C24 C23 119.9(4) . . ?
C24 C25 C26 119.4(4) . . ?
C27 C26 C25 117.6(4) . . ?
C31 C26 C25 124.8(4) . . ?
C31 C26 C27 117.6(4) . . ?
N2 C27 C26 121.9(3) . . ?
N2 C27 C28 115.8(3) . . ?
C26 C27 C28 122.2(3) . . ?
O1 C28 C27 120.5(3) . . ?
O1 C28 C29 123.0(3) . . ?
C29 C28 C27 116.4(3) . . ?
C30 C29 C28 121.4(4) . . ?
C31 C30 C29 120.1(4) . . ?
F1 C31 C26 118.3(4) . . ?
F1 C31 C30 119.6(4) . . ?
C30 C31 C26 122.2(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1980053'
loop_
_audit_author_name
_audit_author_address
a-d
;Yulin Normal University
China
;
_audit_update_record             
;
2020-01-27 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H19 F Ir N5 O, 2(C H4 O)'
_chemical_formula_sum            'C29 H27 F Ir N5 O3'
_chemical_formula_weight         704.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.7444(8)
_cell_length_b                   22.9897(12)
_cell_length_c                   10.6487(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.221(6)
_cell_angle_gamma                90
_cell_volume                     2614.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5857
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2880
_cell_measurement_theta_min      3.8330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20028
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.196
_diffrn_reflns_theta_min         3.358
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  60.00   1.00   15.00    --   18.63 -99.00 150.00   39
  2  ω    -76.00 -51.00   1.00   15.00    --  -18.94 178.00 150.00   25
  3  ω    -82.00  11.00   1.00   15.00    --  -18.94 -77.00-120.00   93
  4  ω    -28.00  -2.00   1.00   15.00    --  -18.94 -57.00   0.00   26
  5  ω    -45.00  50.00   1.00   15.00    --  -18.94  77.00   0.00   95
  6  ω    -89.00  11.00   1.00   15.00    --  -18.94 -19.00  60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0577584000
_diffrn_orient_matrix_UB_12      -0.0000387000
_diffrn_orient_matrix_UB_13      -0.0263696000
_diffrn_orient_matrix_UB_21      -0.0292116000
_diffrn_orient_matrix_UB_22      0.0135920000
_diffrn_orient_matrix_UB_23      -0.0554505000
_diffrn_orient_matrix_UB_31      0.0144070000
_diffrn_orient_matrix_UB_32      0.0276872000
_diffrn_orient_matrix_UB_33      0.0271396000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4282
_reflns_number_total             6202
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.496
_refine_diff_density_min         -1.625
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0972
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C24(H24),
  C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.26982(2) 0.61940(2) 0.88783(2) 0.03403(9) Uani 1 1 d . . . . .
F1 F 0.0429(5) 0.53521(17) 0.3160(4) 0.0827(16) Uani 1 1 d . . . . .
O1 O 0.3708(4) 0.58755(17) 0.7348(4) 0.0448(11) Uani 1 1 d . . . . .
N1 N 0.3390(5) 0.5224(2) 1.0490(5) 0.0452(14) Uani 1 1 d . . . . .
N2 N 0.2517(5) 0.5381(2) 0.9527(5) 0.0427(14) Uani 1 1 d . . . . .
N3 N 0.1222(5) 0.60953(18) 0.7368(5) 0.0391(13) Uani 1 1 d . . . . .
N4 N 0.2291(5) 0.74196(19) 0.9192(5) 0.0383(12) Uani 1 1 d . . . . .
N5 N 0.2919(5) 0.70491(19) 0.8486(5) 0.0345(12) Uani 1 1 d . . . . .
C1 C 0.1635(6) 0.6550(2) 1.0104(5) 0.0353(14) Uani 1 1 d . . . . .
C2 C 0.0915(7) 0.6291(3) 1.0958(6) 0.0461(17) Uani 1 1 d . . . . .
H2 H 0.0955 0.5890 1.1059 0.055 Uiso 1 1 calc R . . . .
C3 C 0.0144(7) 0.6605(3) 1.1663(6) 0.0541(19) Uani 1 1 d . . . . .
H3 H -0.0337 0.6414 1.2210 0.065 Uiso 1 1 calc R . . . .
C4 C 0.0089(7) 0.7208(3) 1.1552(7) 0.056(2) Uani 1 1 d . . . . .
H4 H -0.0427 0.7422 1.2026 0.068 Uiso 1 1 calc R . . . .
C5 C 0.0807(7) 0.7487(3) 1.0732(7) 0.0499(18) Uani 1 1 d . . . . .
H5 H 0.0785 0.7890 1.0649 0.060 Uiso 1 1 calc R . . . .
C6 C 0.1550(6) 0.7158(2) 1.0046(6) 0.0357(14) Uani 1 1 d . . . . .
C7 C 0.2588(7) 0.7973(3) 0.8908(6) 0.0475(18) Uani 1 1 d . . . . .
H7 H 0.2285 0.8306 0.9267 0.057 Uiso 1 1 calc R . . . .
C8 C 0.3395(7) 0.7963(3) 0.8020(7) 0.055(2) Uani 1 1 d . . . . .
H8 H 0.3750 0.8281 0.7653 0.066 Uiso 1 1 calc R . . . .
C9 C 0.3581(6) 0.7377(3) 0.7768(6) 0.0454(16) Uani 1 1 d . . . . .
H9 H 0.4092 0.7235 0.7185 0.054 Uiso 1 1 calc R . . . .
C10 C 0.1726(8) 0.4937(3) 0.9344(6) 0.0534(19) Uani 1 1 d . . . . .
H10 H 0.1038 0.4924 0.8734 0.064 Uiso 1 1 calc R . . . .
C11 C 0.2083(9) 0.4489(3) 1.0208(7) 0.064(2) Uani 1 1 d . . . . .
H11 H 0.1679 0.4135 1.0289 0.077 Uiso 1 1 calc R . . . .
C12 C 0.3142(9) 0.4680(3) 1.0900(7) 0.062(2) Uani 1 1 d . . . . .
H12 H 0.3612 0.4476 1.1539 0.074 Uiso 1 1 calc R . . . .
C13 C 0.4319(7) 0.5638(3) 1.0874(6) 0.0494(18) Uani 1 1 d . . . . .
C14 C 0.5271(8) 0.5533(3) 1.1818(7) 0.062(2) Uani 1 1 d . . . . .
H14 H 0.5324 0.5177 1.2237 0.074 Uiso 1 1 calc R . . . .
C15 C 0.6143(8) 0.5962(4) 1.2134(7) 0.073(3) Uani 1 1 d . . . . .
H15 H 0.6790 0.5897 1.2771 0.088 Uiso 1 1 calc R . . . .
C16 C 0.6059(7) 0.6484(4) 1.1513(8) 0.068(2) Uani 1 1 d . . . . .
H16 H 0.6653 0.6772 1.1731 0.082 Uiso 1 1 calc R . . . .
C17 C 0.5097(7) 0.6590(3) 1.0561(6) 0.0527(18) Uani 1 1 d . . . . .
H17 H 0.5054 0.6948 1.0155 0.063 Uiso 1 1 calc R . . . .
C18 C 0.4190(7) 0.6168(3) 1.0200(6) 0.0427(16) Uani 1 1 d . . . . .
C19 C 0.2917(7) 0.5737(3) 0.6335(6) 0.0452(17) Uani 1 1 d . . . . .
C20 C 0.3330(8) 0.5492(3) 0.5253(7) 0.061(2) Uani 1 1 d . . . . .
H20 H 0.4176 0.5408 0.5240 0.073 Uiso 1 1 calc R . . . .
C21 C 0.2484(9) 0.5370(3) 0.4189(7) 0.064(2) Uani 1 1 d . . . . .
H21 H 0.2778 0.5211 0.3474 0.077 Uiso 1 1 calc R . . . .
C22 C 0.1247(9) 0.5481(3) 0.4185(6) 0.054(2) Uani 1 1 d . . . . .
C23 C 0.0767(8) 0.5736(2) 0.5240(6) 0.0483(19) Uani 1 1 d . . . . .
C24 C -0.0506(8) 0.5865(3) 0.5293(7) 0.060(2) Uani 1 1 d . . . . .
H24 H -0.1092 0.5793 0.4602 0.072 Uiso 1 1 calc R . . . .
C25 C -0.0862(7) 0.6096(3) 0.6363(8) 0.057(2) Uani 1 1 d . . . . .
H25 H -0.1701 0.6184 0.6410 0.068 Uiso 1 1 calc R . . . .
C26 C 0.0026(6) 0.6207(2) 0.7413(6) 0.0435(16) Uani 1 1 d . . . . .
H26 H -0.0238 0.6360 0.8147 0.052 Uiso 1 1 calc R . . . .
C27 C 0.1608(7) 0.5857(2) 0.6296(6) 0.0406(16) Uani 1 1 d . . . . .
O2 O 0.5883(6) 0.6340(4) 0.6857(6) 0.103(2) Uani 1 1 d . . . . .
H2A H 0.5304 0.6116 0.6940 0.154 Uiso 1 1 calc GR . . . .
C28 C 0.5818(10) 0.6525(6) 0.5582(10) 0.148(5) Uani 1 1 d . . . . .
H28A H 0.6133 0.6224 0.5079 0.222 Uiso 1 1 calc GR . . . .
H28B H 0.6314 0.6870 0.5530 0.222 Uiso 1 1 calc GR . . . .
H28C H 0.4964 0.6608 0.5273 0.222 Uiso 1 1 calc GR . . . .
O3 O 0.7690(11) 0.6983(6) 0.8114(15) 0.216(6) Uani 1 1 d . . . . .
H3A H 0.7021 0.6812 0.7962 0.325 Uiso 1 1 calc GR . . . .
C29 C 0.7563(12) 0.7416(6) 0.8952(11) 0.143(5) Uani 1 1 d . . . . .
H29A H 0.6830 0.7640 0.8678 0.214 Uiso 1 1 calc GR . . . .
H29B H 0.8287 0.7663 0.9004 0.214 Uiso 1 1 calc GR . . . .
H29C H 0.7481 0.7252 0.9768 0.214 Uiso 1 1 calc GR . . . .


_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 O1 2.180(4) . ?
Ir1 N2 2.009(5) . ?
Ir1 N3 2.145(5) . ?
Ir1 N5 2.029(4) . ?
Ir1 C1 1.999(6) . ?
Ir1 C18 2.016(7) . ?
F1 C22 1.358(8) . ?
O1 C19 1.338(8) . ?
N1 N2 1.361(7) . ?
N1 C12 1.359(8) . ?
N1 C13 1.408(8) . ?
N2 C10 1.330(8) . ?
N3 C26 1.316(8) . ?
N3 C27 1.371(8) . ?
N4 N5 1.363(7) . ?
N4 C6 1.407(8) . ?
N4 C7 1.353(7) . ?
N5 C9 1.333(7) . ?
C1 C2 1.390(8) . ?
C1 C6 1.402(7) . ?
C2 C3 1.380(9) . ?
C3 C4 1.392(8) . ?
C4 C5 1.384(9) . ?
C5 C6 1.367(8) . ?
C7 C8 1.351(9) . ?
C8 C9 1.392(8) . ?
C10 C11 1.406(9) . ?
C11 C12 1.360(10) . ?
C13 C14 1.375(9) . ?
C13 C18 1.414(8) . ?
C14 C15 1.377(11) . ?
C15 C16 1.369(11) . ?
C16 C17 1.389(9) . ?
C17 C18 1.397(9) . ?
C19 C20 1.397(9) . ?
C19 C27 1.429(10) . ?
C20 C21 1.402(10) . ?
C21 C22 1.354(10) . ?
C22 C23 1.412(10) . ?
C23 C24 1.407(10) . ?
C23 C27 1.393(9) . ?
C24 C25 1.350(10) . ?
C25 C26 1.412(9) . ?
O2 C28 1.418(10) . ?
O3 C29 1.354(12) . ?

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 O1 91.10(18) . . ?
N2 Ir1 N3 93.91(19) . . ?
N2 Ir1 N5 171.8(2) . . ?
N2 Ir1 C18 80.3(2) . . ?
N3 Ir1 O1 77.96(19) . . ?
N5 Ir1 O1 95.32(18) . . ?
N5 Ir1 N3 92.39(18) . . ?
C1 Ir1 O1 172.26(19) . . ?
C1 Ir1 N2 94.2(2) . . ?
C1 Ir1 N3 96.0(2) . . ?
C1 Ir1 N5 80.0(2) . . ?
C1 Ir1 C18 91.3(2) . . ?
C18 Ir1 O1 95.2(2) . . ?
C18 Ir1 N3 171.0(2) . . ?
C18 Ir1 N5 94.0(2) . . ?
C19 O1 Ir1 111.0(4) . . ?
N2 N1 C13 116.6(5) . . ?
C12 N1 N2 110.1(6) . . ?
C12 N1 C13 133.3(6) . . ?
N1 N2 Ir1 115.0(4) . . ?
C10 N2 Ir1 138.4(5) . . ?
C10 N2 N1 106.5(5) . . ?
C26 N3 Ir1 126.7(4) . . ?
C26 N3 C27 119.5(6) . . ?
C27 N3 Ir1 113.6(5) . . ?
N5 N4 C6 116.0(5) . . ?
C7 N4 N5 108.7(5) . . ?
C7 N4 C6 135.2(6) . . ?
N4 N5 Ir1 114.6(4) . . ?
C9 N5 Ir1 138.4(4) . . ?
C9 N5 N4 106.9(5) . . ?
C2 C1 Ir1 130.6(4) . . ?
C2 C1 C6 114.6(6) . . ?
C6 C1 Ir1 114.7(4) . . ?
C3 C2 C1 122.9(6) . . ?
C2 C3 C4 119.8(7) . . ?
C5 C4 C3 119.6(6) . . ?
C6 C5 C4 118.6(6) . . ?
C1 C6 N4 114.6(5) . . ?
C5 C6 N4 120.8(5) . . ?
C5 C6 C1 124.6(6) . . ?
C8 C7 N4 109.0(6) . . ?
C7 C8 C9 105.6(6) . . ?
N5 C9 C8 109.8(6) . . ?
N2 C10 C11 110.0(7) . . ?
C12 C11 C10 105.7(6) . . ?
N1 C12 C11 107.8(7) . . ?
N1 C13 C18 114.1(6) . . ?
C14 C13 N1 122.7(6) . . ?
C14 C13 C18 123.1(7) . . ?
C13 C14 C15 119.0(7) . . ?
C16 C15 C14 120.2(7) . . ?
C15 C16 C17 120.6(8) . . ?
C16 C17 C18 121.5(7) . . ?
C13 C18 Ir1 114.0(5) . . ?
C17 C18 Ir1 130.5(5) . . ?
C17 C18 C13 115.5(6) . . ?
O1 C19 C20 122.0(7) . . ?
O1 C19 C27 120.9(6) . . ?
C20 C19 C27 117.0(7) . . ?
C19 C20 C21 120.7(8) . . ?
C22 C21 C20 121.0(7) . . ?
F1 C22 C23 118.0(8) . . ?
C21 C22 F1 120.7(7) . . ?
C21 C22 C23 121.3(7) . . ?
C24 C23 C22 124.0(7) . . ?
C27 C23 C22 117.7(8) . . ?
C27 C23 C24 118.3(7) . . ?
C25 C24 C23 118.8(7) . . ?
C24 C25 C26 120.7(7) . . ?
N3 C26 C25 121.0(7) . . ?
N3 C27 C19 116.1(6) . . ?
N3 C27 C23 121.6(7) . . ?
C23 C27 C19 122.4(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.597
_oxdiff_exptl_absorpt_empirical_full_min 0.554
####################################################################### 
# 
# 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_64
_database_code_depnum_ccdc_archive 'CCDC 1980051'
loop_
_audit_author_name
_audit_author_address
a-d
;Yulin Normal University
China
;
_audit_update_record             
;
2020-01-27 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C35 H21 F Ir N3 O'
_chemical_formula_sum            'C35 H21 F Ir N3 O'
_chemical_formula_weight         710.77
_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 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4440 7.9890 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   21.5039(6)
_cell_length_b                   16.6692(5)
_cell_length_c                   14.8357(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.136(3)
_cell_angle_gamma                90
_cell_volume                     5217.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.7120
_cell_measurement_theta_min      3.6520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2768
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18790
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.290
_diffrn_reflns_theta_min         3.362
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00  60.50   0.90   25.00    --   18.63 -99.00 150.00   45
  2  ω    -89.00  10.00   0.90   25.00    --  -18.94 -77.00-120.00  110
  3  ω    -27.00   0.00   0.90   25.00    --  -18.94 -57.00   0.00   30
  4  ω    -45.00  46.80   0.90   25.00    --  -18.94  77.00   0.00  102
  5  ω    -85.00   9.50   0.90   25.00    --  -18.94 -19.00  60.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0129973000
_diffrn_orient_matrix_UB_12      -0.0362622000
_diffrn_orient_matrix_UB_13      0.0132539000
_diffrn_orient_matrix_UB_21      0.0307169000
_diffrn_orient_matrix_UB_22      -0.0128805000
_diffrn_orient_matrix_UB_23      0.0215485000
_diffrn_orient_matrix_UB_31      -0.0041660000
_diffrn_orient_matrix_UB_32      0.0181744000
_diffrn_orient_matrix_UB_33      0.0416450000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3953
_reflns_number_total             6270
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.259
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0104P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0516
_refine_ls_wR_factor_ref         0.0624
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C0AA(H0AA), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27), C29(H29), C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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 0.16253(2) 0.41077(2) 0.16272(2) 0.03500(7) Uani 1 1 d . . . . .
F1 F -0.00389(16) 0.0783(2) 0.1407(2) 0.0783(12) Uani 1 1 d . . . . .
O1 O 0.07458(16) 0.3808(2) 0.0737(2) 0.0412(10) Uani 1 1 d . . . . .
N1 N 0.1470(2) 0.2918(3) 0.2056(3) 0.0363(12) Uani 1 1 d . . . . .
N2 N 0.2160(2) 0.3740(3) 0.0705(3) 0.0370(12) Uani 1 1 d . . . . .
C3 C 0.2491(2) 0.4261(3) 0.2413(3) 0.0363(14) Uani 1 1 d . . . . .
C4 C 0.1669(2) 0.5245(3) 0.1214(3) 0.0376(14) Uani 1 1 d . . . . .
N5 N 0.11346(19) 0.4645(3) 0.2527(3) 0.0389(12) Uani 1 1 d . . . . .
C1 C 0.0545(3) 0.3092(4) 0.0889(3) 0.0367(14) Uani 1 1 d . . . . .
C2 C -0.0014(3) 0.2756(4) 0.0405(4) 0.0540(18) Uani 1 1 d . . . . .
H2 H -0.0266 0.3056 -0.0054 0.065 Uiso 1 1 calc R . . . .
C0AA C -0.0207(3) 0.1988(4) 0.0586(4) 0.063(2) Uani 1 1 d . . . . .
H0AA H -0.0582 0.1781 0.0246 0.075 Uiso 1 1 calc R . . . .
C1AA C 0.0143(3) 0.1544(4) 0.1248(5) 0.0557(18) Uani 1 1 d . . . . .
C5 C 0.0713(3) 0.1815(4) 0.1780(4) 0.0454(16) Uani 1 1 d . . . . .
C6 C 0.1109(3) 0.1383(4) 0.2482(4) 0.0524(17) Uani 1 1 d . . . . .
H6 H 0.0991 0.0876 0.2650 0.063 Uiso 1 1 calc R . . . .
C7 C 0.1665(3) 0.1715(4) 0.2911(4) 0.0561(18) Uani 1 1 d . . . . .
H7 H 0.1937 0.1423 0.3356 0.067 Uiso 1 1 calc R . . . .
C8 C 0.1829(3) 0.2485(4) 0.2691(3) 0.0475(17) Uani 1 1 d . . . . .
H8 H 0.2208 0.2702 0.3004 0.057 Uiso 1 1 calc R . . . .
C9 C 0.0904(2) 0.2595(4) 0.1599(3) 0.0373(14) Uani 1 1 d . . . . .
C10 C 0.1946(3) 0.3494(3) -0.0154(3) 0.0423(15) Uani 1 1 d . . . . .
H10 H 0.1514 0.3408 -0.0353 0.051 Uiso 1 1 calc R . . . .
C11 C 0.2357(3) 0.3366(4) -0.0754(4) 0.0558(18) Uani 1 1 d . . . . .
H11 H 0.2198 0.3213 -0.1358 0.067 Uiso 1 1 calc R . . . .
C12 C 0.2989(3) 0.3463(4) -0.0465(4) 0.0576(19) Uani 1 1 d . . . . .
H12 H 0.3262 0.3376 -0.0871 0.069 Uiso 1 1 calc R . . . .
C13 C 0.3232(3) 0.3690(4) 0.0436(4) 0.0469(16) Uani 1 1 d . . . . .
C14 C 0.3882(3) 0.3803(4) 0.0831(5) 0.061(2) Uani 1 1 d . . . . .
H14 H 0.4186 0.3711 0.0475 0.073 Uiso 1 1 calc R . . . .
C15 C 0.4068(3) 0.4042(4) 0.1714(5) 0.0591(18) Uani 1 1 d . . . . .
H15 H 0.4497 0.4122 0.1943 0.071 Uiso 1 1 calc R . . . .
C16 C 0.3630(3) 0.4174(4) 0.2300(4) 0.0472(15) Uani 1 1 d . . . . .
C17 C 0.3788(3) 0.4401(4) 0.3232(4) 0.0597(19) Uani 1 1 d . . . . .
H17 H 0.4211 0.4454 0.3516 0.072 Uiso 1 1 calc R . . . .
C18 C 0.3325(3) 0.4543(4) 0.3717(4) 0.061(2) Uani 1 1 d . . . . .
H18 H 0.3440 0.4682 0.4334 0.074 Uiso 1 1 calc R . . . .
C19 C 0.2680(3) 0.4488(3) 0.3320(4) 0.0521(17) Uani 1 1 d . . . . .
H19 H 0.2377 0.4605 0.3671 0.063 Uiso 1 1 calc R . . . .
C20 C 0.2979(2) 0.4103(3) 0.1932(3) 0.0335(12) Uani 1 1 d . . . . .
C21 C 0.2802(2) 0.3831(3) 0.1007(4) 0.0361(14) Uani 1 1 d . . . . .
C22 C 0.1928(3) 0.5604(4) 0.0524(3) 0.0445(16) Uani 1 1 d . . . . .
H22 H 0.2127 0.5281 0.0155 0.053 Uiso 1 1 calc R . . . .
C23 C 0.1899(3) 0.6437(4) 0.0363(4) 0.0570(19) Uani 1 1 d . . . . .
H23 H 0.2072 0.6646 -0.0115 0.068 Uiso 1 1 calc R . . . .
C24 C 0.1624(3) 0.6943(4) 0.0892(4) 0.0595(19) Uani 1 1 d . . . . .
H24 H 0.1615 0.7492 0.0783 0.071 Uiso 1 1 calc R . . . .
C25 C 0.1355(3) 0.6623(4) 0.1607(4) 0.0454(16) Uani 1 1 d . . . . .
C26 C 0.1045(3) 0.7103(4) 0.2178(5) 0.065(2) Uani 1 1 d . . . . .
H26 H 0.1027 0.7656 0.2093 0.078 Uiso 1 1 calc R . . . .
C27 C 0.0778(3) 0.6774(4) 0.2835(5) 0.065(2) Uani 1 1 d . . . . .
H27 H 0.0579 0.7108 0.3195 0.078 Uiso 1 1 calc R . . . .
C28 C 0.0787(2) 0.5928(4) 0.3005(4) 0.0449(15) Uani 1 1 d . . . . .
C29 C 0.0502(3) 0.5530(5) 0.3653(4) 0.058(2) Uani 1 1 d . . . . .
H29 H 0.0295 0.5821 0.4042 0.070 Uiso 1 1 calc R . . . .
C30 C 0.0529(3) 0.4719(5) 0.3712(4) 0.0565(19) Uani 1 1 d . . . . .
H30 H 0.0332 0.4453 0.4131 0.068 Uiso 1 1 calc R . . . .
C31 C 0.0855(2) 0.4281(4) 0.3143(4) 0.0466(16) Uani 1 1 d . . . . .
H31 H 0.0877 0.3725 0.3197 0.056 Uiso 1 1 calc R . . . .
C32 C 0.1096(3) 0.5460(4) 0.2448(4) 0.0408(15) Uani 1 1 d . . . . .
C33 C 0.1381(2) 0.5786(4) 0.1744(3) 0.0396(14) 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 O1 2.146(3) . ?
Ir1 N1 2.128(4) . ?
Ir1 N2 2.044(4) . ?
Ir1 C3 2.012(5) . ?
Ir1 C4 2.000(6) . ?
Ir1 N5 2.060(4) . ?
F1 C1AA 1.362(7) . ?
O1 C1 1.303(6) . ?
N1 C8 1.313(6) . ?
N1 C9 1.382(6) . ?
N2 C10 1.334(5) . ?
N2 C21 1.373(6) . ?
C3 C19 1.381(6) . ?
C3 C20 1.404(6) . ?
C4 C22 1.391(7) . ?
C4 C33 1.416(7) . ?
N5 C31 1.332(6) . ?
N5 C32 1.365(6) . ?
C1 C2 1.392(7) . ?
C1 C9 1.442(7) . ?
C2 C0AA 1.388(8) . ?
C0AA C1AA 1.340(8) . ?
C1AA C5 1.398(7) . ?
C5 C6 1.410(7) . ?
C5 C9 1.405(7) . ?
C6 C7 1.357(7) . ?
C7 C8 1.387(7) . ?
C10 C11 1.388(7) . ?
C11 C12 1.354(7) . ?
C12 C13 1.390(7) . ?
C13 C14 1.421(7) . ?
C13 C21 1.390(7) . ?
C14 C15 1.353(7) . ?
C15 C16 1.417(7) . ?
C16 C17 1.411(7) . ?
C16 C20 1.406(6) . ?
C17 C18 1.357(8) . ?
C18 C19 1.401(7) . ?
C20 C21 1.424(6) . ?
C22 C23 1.408(7) . ?
C23 C24 1.363(8) . ?
C24 C25 1.408(7) . ?
C25 C26 1.421(8) . ?
C25 C33 1.410(7) . ?
C26 C27 1.340(8) . ?
C27 C28 1.431(8) . ?
C28 C29 1.404(8) . ?
C28 C32 1.396(7) . ?
C29 C30 1.354(8) . ?
C30 C31 1.402(7) . ?
C32 C33 1.416(7) . ?

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
N1 Ir1 O1 78.24(15) . . ?
N2 Ir1 O1 93.54(15) . . ?
N2 Ir1 N1 93.57(16) . . ?
N2 Ir1 N5 171.55(19) . . ?
C3 Ir1 O1 172.99(18) . . ?
C3 Ir1 N1 97.25(19) . . ?
C3 Ir1 N2 81.31(18) . . ?
C3 Ir1 N5 95.80(18) . . ?
C4 Ir1 O1 96.91(17) . . ?
C4 Ir1 N1 173.69(18) . . ?
C4 Ir1 N2 90.7(2) . . ?
C4 Ir1 C3 87.9(2) . . ?
C4 Ir1 N5 81.2(2) . . ?
N5 Ir1 O1 89.95(14) . . ?
N5 Ir1 N1 94.66(18) . . ?
C1 O1 Ir1 112.9(3) . . ?
C8 N1 Ir1 128.5(4) . . ?
C8 N1 C9 118.5(5) . . ?
C9 N1 Ir1 113.0(4) . . ?
C10 N2 Ir1 126.6(4) . . ?
C10 N2 C21 119.1(5) . . ?
C21 N2 Ir1 114.1(3) . . ?
C19 C3 Ir1 131.7(4) . . ?
C19 C3 C20 116.0(5) . . ?
C20 C3 Ir1 112.3(3) . . ?
C22 C4 Ir1 133.1(5) . . ?
C22 C4 C33 114.5(5) . . ?
C33 C4 Ir1 112.4(4) . . ?
C31 N5 Ir1 127.0(4) . . ?
C31 N5 C32 119.0(5) . . ?
C32 N5 Ir1 114.0(4) . . ?
O1 C1 C2 124.1(5) . . ?
O1 C1 C9 120.2(5) . . ?
C2 C1 C9 115.7(6) . . ?
C0AA C2 C1 122.1(6) . . ?
C1AA C0AA C2 120.3(6) . . ?
F1 C1AA C5 117.0(6) . . ?
C0AA C1AA F1 120.1(6) . . ?
C0AA C1AA C5 122.9(7) . . ?
C1AA C5 C6 126.2(6) . . ?
C1AA C5 C9 116.6(6) . . ?
C9 C5 C6 117.1(6) . . ?
C7 C6 C5 119.3(6) . . ?
C6 C7 C8 120.5(6) . . ?
N1 C8 C7 122.5(6) . . ?
N1 C9 C1 115.6(5) . . ?
N1 C9 C5 122.0(5) . . ?
C5 C9 C1 122.4(5) . . ?
N2 C10 C11 121.0(5) . . ?
C12 C11 C10 120.2(5) . . ?
C11 C12 C13 120.3(6) . . ?
C12 C13 C14 126.1(6) . . ?
C21 C13 C12 117.5(5) . . ?
C21 C13 C14 116.3(5) . . ?
C15 C14 C13 121.5(6) . . ?
C14 C15 C16 122.2(6) . . ?
C17 C16 C15 125.5(6) . . ?
C20 C16 C15 118.6(5) . . ?
C20 C16 C17 115.9(5) . . ?
C18 C17 C16 120.3(6) . . ?
C17 C18 C19 122.3(6) . . ?
C3 C19 C18 120.6(6) . . ?
C3 C20 C16 124.9(5) . . ?
C3 C20 C21 117.6(4) . . ?
C16 C20 C21 117.5(5) . . ?
N2 C21 C13 121.8(5) . . ?
N2 C21 C20 114.4(5) . . ?
C13 C21 C20 123.7(5) . . ?
C4 C22 C23 122.7(6) . . ?
C24 C23 C22 121.4(6) . . ?
C23 C24 C25 119.2(6) . . ?
C24 C25 C26 123.0(7) . . ?
C24 C25 C33 118.2(6) . . ?
C33 C25 C26 118.8(6) . . ?
C27 C26 C25 121.3(7) . . ?
C26 C27 C28 122.5(7) . . ?
C29 C28 C27 126.4(7) . . ?
C32 C28 C27 116.1(6) . . ?
C32 C28 C29 117.5(7) . . ?
C30 C29 C28 119.8(6) . . ?
C29 C30 C31 120.1(6) . . ?
N5 C31 C30 121.3(6) . . ?
N5 C32 C28 122.3(6) . . ?
N5 C32 C33 114.8(5) . . ?
C28 C32 C33 123.0(6) . . ?
C25 C33 C4 124.0(6) . . ?
C25 C33 C32 118.4(6) . . ?
C32 C33 C4 117.5(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.859
####################################################################### 
# 
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 1980052'
loop_
_audit_author_name
_audit_author_address
a-d
;Yulin Normal University
China
;
_audit_update_record             
;
2020-01-27 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C33 H25 F Ir N3 O'
_chemical_formula_sum            'C33 H25 F Ir N3 O'
_chemical_formula_weight         690.76
_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'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   20.4836(17)
_cell_length_b                   16.3026(14)
_cell_length_c                   15.6214(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.056(3)
_cell_angle_gamma                90
_cell_volume                     5136.4(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9405
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.520
_cell_measurement_theta_min      2.943
_shelx_estimated_absorpt_T_max   0.511
_shelx_estimated_absorpt_T_min   0.274
_exptl_absorpt_coefficient_mu    5.239
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1548 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.5634.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2704
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.148
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            52961
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.943
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5028
_reflns_number_total             5921
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5921
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0210
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²+8.8322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0513
_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:
 C1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C31(H31), C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.16984(2) 0.07695(2) 0.16514(2) 0.03052(4) Uani 1 1 d . . . . .
F1 F -0.00655(13) 0.41718(12) 0.14435(19) 0.0772(7) Uani 1 1 d . . . . .
O1 O 0.07874(10) 0.10829(13) 0.07906(13) 0.0403(5) Uani 1 1 d . . . . .
N1 N 0.11642(12) 0.01933(15) 0.24623(15) 0.0352(5) Uani 1 1 d . . . . .
N2 N 0.15226(12) 0.19993(14) 0.20408(15) 0.0337(5) Uani 1 1 d . . . . .
N3 N 0.23149(12) 0.11816(15) 0.08525(16) 0.0370(5) Uani 1 1 d . . . . .
C1 C 0.08764(17) 0.0602(2) 0.3045(2) 0.0480(8) Uani 1 1 d . . . . .
H1 H 0.0888 0.1173 0.3047 0.058 Uiso 1 1 calc R . . . .
C2 C 0.05661(19) 0.0206(2) 0.3637(2) 0.0575(10) Uani 1 1 d . . . . .
H2 H 0.0361 0.0501 0.4025 0.069 Uiso 1 1 calc R . . . .
C3 C 0.05655(19) -0.0625(3) 0.3645(2) 0.0595(10) Uani 1 1 d . . . . .
H3 H 0.0369 -0.0900 0.4056 0.071 Uiso 1 1 calc R . . . .
C4 C 0.08512(17) -0.1073(2) 0.3053(2) 0.0500(8) Uani 1 1 d . . . . .
C5 C 0.0847(3) -0.1992(3) 0.3126(3) 0.0876(15) Uani 1 1 d . . . . .
H5A H 0.0691 -0.2147 0.3648 0.131 Uiso 1 1 calc GR . . . .
H5B H 0.1288 -0.2198 0.3145 0.131 Uiso 1 1 calc GR . . . .
H5C H 0.0559 -0.2219 0.2632 0.131 Uiso 1 1 calc GR . . . .
C6 C 0.11453(15) -0.06453(18) 0.2428(2) 0.0374(7) Uani 1 1 d . . . . .
C7 C 0.14398(15) -0.09844(19) 0.1708(2) 0.0394(7) Uani 1 1 d . . . . .
C8 C 0.14299(17) -0.1805(2) 0.1452(2) 0.0502(8) Uani 1 1 d . . . . .
H8 H 0.1237 -0.2195 0.1764 0.060 Uiso 1 1 calc R . . . .
C9 C 0.17018(18) -0.2045(2) 0.0744(3) 0.0573(10) Uani 1 1 d . . . . .
H9 H 0.1700 -0.2596 0.0591 0.069 Uiso 1 1 calc R . . . .
C10 C 0.19741(18) -0.1478(2) 0.0267(2) 0.0541(9) Uani 1 1 d . . . . .
H10 H 0.2144 -0.1639 -0.0221 0.065 Uiso 1 1 calc R . . . .
C11 C 0.19959(18) -0.0658(2) 0.0516(2) 0.0466(8) Uani 1 1 d . . . . .
H11 H 0.2190 -0.0279 0.0193 0.056 Uiso 1 1 calc R . . . .
C12 C 0.17348(14) -0.03855(18) 0.12372(19) 0.0352(6) Uani 1 1 d . . . . .
C13 C 0.25708(15) 0.06454(16) 0.2435(2) 0.0348(6) Uani 1 1 d . . . . .
C14 C 0.26839(17) 0.0455(2) 0.3319(2) 0.0467(8) Uani 1 1 d . . . . .
H14 H 0.2329 0.0287 0.3576 0.056 Uiso 1 1 calc R . . . .
C15 C 0.33072(19) 0.0508(2) 0.3824(3) 0.0568(9) Uani 1 1 d . . . . .
H15 H 0.3365 0.0381 0.4413 0.068 Uiso 1 1 calc R . . . .
C16 C 0.38397(19) 0.0746(2) 0.3466(3) 0.0609(10) Uani 1 1 d . . . . .
H16 H 0.4256 0.0794 0.3812 0.073 Uiso 1 1 calc R . . . .
C17 C 0.37558(18) 0.0915(2) 0.2587(3) 0.0548(9) Uani 1 1 d . . . . .
H17 H 0.4121 0.1063 0.2341 0.066 Uiso 1 1 calc R . . . .
C18 C 0.31310(15) 0.08665(17) 0.2064(2) 0.0389(7) Uani 1 1 d . . . . .
C19 C 0.29767(15) 0.10913(18) 0.1139(2) 0.0396(7) Uani 1 1 d . . . . .
C20 C 0.34152(18) 0.1182(2) 0.0542(3) 0.0536(9) Uani 1 1 d . . . . .
C21 C 0.4144(2) 0.0975(3) 0.0750(3) 0.0777(13) Uani 1 1 d . . . . .
H21A H 0.4380 0.1418 0.1069 0.116 Uiso 1 1 calc GR . . . .
H21B H 0.4310 0.0890 0.0219 0.116 Uiso 1 1 calc GR . . . .
H21C H 0.4204 0.0484 0.1094 0.116 Uiso 1 1 calc GR . . . .
C22 C 0.3147(2) 0.1417(2) -0.0300(3) 0.0661(11) Uani 1 1 d . . . . .
H22 H 0.3428 0.1485 -0.0702 0.079 Uiso 1 1 calc R . . . .
C23 C 0.2491(2) 0.1549(2) -0.0553(3) 0.0632(11) Uani 1 1 d . . . . .
H23 H 0.2324 0.1727 -0.1114 0.076 Uiso 1 1 calc R . . . .
C24 C 0.20761(19) 0.1415(2) 0.0033(2) 0.0483(8) Uani 1 1 d . . . . .
H24 H 0.1622 0.1487 -0.0140 0.058 Uiso 1 1 calc R . . . .
C25 C 0.05661(15) 0.18097(19) 0.09456(19) 0.0376(7) Uani 1 1 d . . . . .
C26 C -0.00252(17) 0.2136(2) 0.0498(2) 0.0515(8) Uani 1 1 d . . . . .
H26 H -0.0286 0.1823 0.0072 0.062 Uiso 1 1 calc R . . . .
C27 C -0.02335(18) 0.2922(2) 0.0677(3) 0.0582(10) Uani 1 1 d . . . . .
H27 H -0.0631 0.3124 0.0370 0.070 Uiso 1 1 calc R . . . .
C28 C 0.01362(18) 0.3394(2) 0.1293(3) 0.0530(9) Uani 1 1 d . . . . .
C29 C 0.07367(16) 0.31259(19) 0.1781(2) 0.0408(7) Uani 1 1 d . . . . .
C30 C 0.09421(14) 0.23202(18) 0.15977(18) 0.0334(6) Uani 1 1 d . . . . .
C31 C 0.11577(18) 0.3587(2) 0.2403(2) 0.0507(8) Uani 1 1 d . . . . .
H31 H 0.1039 0.4117 0.2535 0.061 Uiso 1 1 calc R . . . .
C32 C 0.17360(19) 0.3263(2) 0.2811(2) 0.0526(9) Uani 1 1 d . . . . .
H32 H 0.2020 0.3571 0.3218 0.063 Uiso 1 1 calc R . . . .
C33 C 0.19041(16) 0.2460(2) 0.2619(2) 0.0448(7) Uani 1 1 d . . . . .
H33 H 0.2301 0.2241 0.2911 0.054 Uiso 1 1 calc R . . . .


_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 O1 2.162(2) . ?
Ir1 N1 2.042(2) . ?
Ir1 N2 2.144(2) . ?
Ir1 N3 2.038(2) . ?
Ir1 C12 1.997(3) . ?
Ir1 C13 1.992(3) . ?
F1 C28 1.367(4) . ?
O1 C25 1.306(4) . ?
N1 C1 1.345(4) . ?
N1 C6 1.368(4) . ?
N2 C30 1.371(4) . ?
N2 C33 1.320(4) . ?
N3 C19 1.359(4) . ?
N3 C24 1.344(4) . ?
C1 C2 1.372(5) . ?
C2 C3 1.355(5) . ?
C3 C4 1.385(5) . ?
C4 C5 1.503(5) . ?
C4 C6 1.417(5) . ?
C6 C7 1.474(5) . ?
C7 C8 1.395(4) . ?
C7 C12 1.419(5) . ?
C8 C9 1.379(5) . ?
C9 C10 1.367(5) . ?
C10 C11 1.390(5) . ?
C11 C12 1.401(4) . ?
C13 C14 1.395(4) . ?
C13 C18 1.420(4) . ?
C14 C15 1.381(5) . ?
C15 C16 1.365(6) . ?
C16 C17 1.382(6) . ?
C17 C18 1.396(5) . ?
C18 C19 1.471(5) . ?
C19 C20 1.410(4) . ?
C20 C21 1.509(6) . ?
C20 C22 1.388(6) . ?
C22 C23 1.349(6) . ?
C23 C24 1.371(5) . ?
C25 C26 1.394(4) . ?
C25 C30 1.432(4) . ?
C26 C27 1.394(5) . ?
C27 C28 1.356(5) . ?
C28 C29 1.399(5) . ?
C29 C30 1.424(4) . ?
C29 C31 1.400(5) . ?
C31 C32 1.351(5) . ?
C32 C33 1.400(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
N1 Ir1 O1 89.81(9) . . ?
N1 Ir1 N2 96.86(9) . . ?
N2 Ir1 O1 77.64(9) . . ?
N3 Ir1 O1 95.80(9) . . ?
N3 Ir1 N1 171.15(9) . . ?
N3 Ir1 N2 91.04(9) . . ?
C12 Ir1 O1 95.64(10) . . ?
C12 Ir1 N1 79.72(11) . . ?
C12 Ir1 N2 172.55(10) . . ?
C12 Ir1 N3 92.88(11) . . ?
C13 Ir1 O1 172.01(9) . . ?
C13 Ir1 N1 95.29(11) . . ?
C13 Ir1 N2 95.60(10) . . ?
C13 Ir1 N3 79.90(11) . . ?
C13 Ir1 C12 91.33(11) . . ?
C25 O1 Ir1 112.88(18) . . ?
C1 N1 Ir1 122.5(2) . . ?
C1 N1 C6 120.6(3) . . ?
C6 N1 Ir1 116.8(2) . . ?
C30 N2 Ir1 112.80(19) . . ?
C33 N2 Ir1 128.1(2) . . ?
C33 N2 C30 119.1(3) . . ?
C19 N3 Ir1 116.9(2) . . ?
C24 N3 Ir1 121.0(2) . . ?
C24 N3 C19 121.3(3) . . ?
N1 C1 C2 122.2(3) . . ?
C3 C2 C1 118.6(4) . . ?
C2 C3 C4 121.3(3) . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 C6 118.7(3) . . ?
C6 C4 C5 123.5(4) . . ?
N1 C6 C4 118.5(3) . . ?
N1 C6 C7 113.0(3) . . ?
C4 C6 C7 128.4(3) . . ?
C8 C7 C6 126.2(3) . . ?
C8 C7 C12 119.8(3) . . ?
C12 C7 C6 113.9(3) . . ?
C9 C8 C7 120.9(3) . . ?
C10 C9 C8 120.4(3) . . ?
C9 C10 C11 119.6(3) . . ?
C10 C11 C12 122.1(3) . . ?
C7 C12 Ir1 115.9(2) . . ?
C11 C12 Ir1 126.9(2) . . ?
C11 C12 C7 117.1(3) . . ?
C14 C13 Ir1 127.4(2) . . ?
C14 C13 C18 117.1(3) . . ?
C18 C13 Ir1 115.2(2) . . ?
C15 C14 C13 121.9(3) . . ?
C16 C15 C14 120.6(4) . . ?
C15 C16 C17 119.6(3) . . ?
C16 C17 C18 120.9(3) . . ?
C13 C18 C19 114.5(3) . . ?
C17 C18 C13 119.9(3) . . ?
C17 C18 C19 125.4(3) . . ?
N3 C19 C18 112.4(2) . . ?
N3 C19 C20 119.0(3) . . ?
C20 C19 C18 128.5(3) . . ?
C19 C20 C21 123.7(4) . . ?
C22 C20 C19 117.5(3) . . ?
C22 C20 C21 118.6(3) . . ?
C23 C22 C20 122.1(3) . . ?
C22 C23 C24 118.7(4) . . ?
N3 C24 C23 121.1(4) . . ?
O1 C25 C26 123.5(3) . . ?
O1 C25 C30 119.9(3) . . ?
C26 C25 C30 116.6(3) . . ?
C27 C26 C25 121.3(3) . . ?
C28 C27 C26 120.8(3) . . ?
F1 C28 C29 117.4(3) . . ?
C27 C28 F1 120.0(3) . . ?
C27 C28 C29 122.6(3) . . ?
C28 C29 C30 116.2(3) . . ?
C28 C29 C31 125.9(3) . . ?
C31 C29 C30 117.9(3) . . ?
N2 C30 C25 116.7(3) . . ?
N2 C30 C29 120.8(3) . . ?
C29 C30 C25 122.6(3) . . ?
C32 C31 C29 120.0(3) . . ?
C31 C32 C33 119.5(3) . . ?
N2 C33 C32 122.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
