# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_yy088
_database_code_depnum_ccdc_archive 'CCDC 2154665'
loop_
_audit_author_name
_audit_author_address
'Youngmee Kim'
;Ewha Womans University
South Korea
;
_audit_update_record             
;
2022-02-25 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            SG-46
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         320.34
_chemical_absolute_configuration .

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   11.6867(10)
_cell_length_b                   19.3211(17)
_cell_length_c                   7.1481(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1614.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5067
_cell_measurement_theta_min      2.7355
_cell_measurement_theta_max      21.8101
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            56517
_diffrn_reflns_av_R_equivalents  0.1273
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             4026
_reflns_number_gt                2506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1372
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         4026
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.6033P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 788 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(10)

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'

_computing_data_collection       'Bruker Instrument Service v2021.1.0.1'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4714(4) 0.9408(2) 0.6842(7) 0.0548(12) Uani d . . . 1 . .
H H1 0.416458 0.958145 0.765883 0.066 Uiso calc U . R 1 . .
C C2 0.5797(5) 0.9703(2) 0.6785(8) 0.0653(15) Uani d . . . 1 . .
H H2 0.597388 1.007131 0.757277 0.078 Uiso calc U . R 1 . .
C C3 0.6602(4) 0.9456(2) 0.5581(8) 0.0612(14) Uani d . . . 1 . .
H H3 0.732248 0.965985 0.554355 0.073 Uiso calc U . R 1 . .
C C4 0.6360(4) 0.8914(2) 0.4430(9) 0.0591(12) Uani d . . . 1 . .
H H4 0.691603 0.87439 0.362003 0.071 Uiso calc U . R 1 . .
C C5 0.5272(3) 0.8613(2) 0.4475(8) 0.0504(11) Uani d . . . 1 . .
H H5 0.510306 0.824558 0.368005 0.061 Uiso calc U . R 1 . .
C C6 0.4452(3) 0.88554(19) 0.5682(6) 0.0389(9) Uani d . . . 1 . .
C C7 0.3258(3) 0.8577(2) 0.5745(6) 0.0388(9) Uani d . . . 1 . .
C C8 0.2141(3) 0.75301(19) 0.4885(5) 0.0336(9) Uani d . . . 1 . .
C C9 0.2233(3) 0.68135(19) 0.4564(6) 0.0384(9) Uani d . . . 1 . .
C C10 0.1227(3) 0.6430(2) 0.4321(7) 0.0456(10) Uani d . . . 1 . .
H H10 0.127324 0.595361 0.414582 0.055 Uiso calc U . R 1 . .
C C11 0.0180(3) 0.6743(2) 0.4337(7) 0.0512(11) Uani d . . . 1 . .
H H11 -0.047425 0.647778 0.415376 0.061 Uiso calc U . R 1 . .
C C12 0.0077(3) 0.7449(2) 0.4622(6) 0.0452(10) Uani d . . . 1 . .
C C13 0.1060(3) 0.7833(2) 0.4894(6) 0.0445(10) Uani d . . . 1 . .
H H13 0.09975 0.830729 0.508903 0.053 Uiso calc U . R 1 . .
C C14 -0.1065(3) 0.7803(3) 0.4534(9) 0.0708(14) Uani d . . . 1 . .
H H14A -0.160909 0.75487 0.527018 0.106 Uiso calc U . R 1 . .
H H14B -0.132102 0.782147 0.325911 0.106 Uiso calc U . R 1 . .
H H14C -0.099654 0.82645 0.501821 0.106 Uiso calc U . R 1 . .
C C15 0.3334(3) 0.64644(18) 0.4434(6) 0.0391(9) Uani d . . . 1 . .
C C16 0.4394(4) 0.5515(2) 0.4153(9) 0.0636(13) Uani d . . . 1 . .
C C17 0.5096(3) 0.6134(2) 0.4288(7) 0.0477(10) Uani d . . . 1 . .
C C18 0.6211(4) 0.6186(3) 0.3209(7) 0.0650(15) Uani d . . . 1 . .
H H18A 0.644132 0.57899 0.24644 0.078 Uiso calc U . R 1 . .
H H18B 0.641326 0.663204 0.268143 0.078 Uiso calc U . R 1 . .
C C19 0.6239(5) 0.6114(3) 0.5258(7) 0.0669(15) Uani d . . . 1 . .
H H19A 0.646111 0.651583 0.598508 0.08 Uiso calc U . R 1 . .
H H19B 0.648916 0.56742 0.576819 0.08 Uiso calc U . R 1 . .
N N1 0.3144(3) 0.79171(16) 0.5121(5) 0.0383(8) Uani d . . . 1 . .
H H1A 0.376992 0.770907 0.48334 0.046 Uiso calc U . R 1 . .
N N2 0.4338(3) 0.67144(15) 0.4436(5) 0.0418(8) Uani d . . . 1 . .
O O1 0.2469(3) 0.89217(14) 0.6347(5) 0.0599(9) Uani d . . . 1 . .
O O2 0.3269(2) 0.57426(13) 0.4279(6) 0.0601(9) Uani d . . . 1 . .
O O3 0.4609(3) 0.49159(16) 0.3988(9) 0.1021(15) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.387(6) ?
C1 C2 . 1.389(6) ?
C1 H1 . 0.93 ?
C2 C3 . 1.361(7) ?
C2 H2 . 0.93 ?
C3 C4 . 1.362(7) ?
C3 H3 . 0.93 ?
C4 C5 . 1.399(5) ?
C4 H4 . 0.93 ?
C5 C6 . 1.372(6) ?
C5 H5 . 0.93 ?
C6 C7 . 1.496(5) ?
C7 O1 . 1.216(5) ?
C7 N1 . 1.358(5) ?
C8 C13 . 1.393(5) ?
C8 N1 . 1.400(5) ?
C8 C9 . 1.408(5) ?
C9 C10 . 1.401(5) ?
C9 C15 . 1.456(5) ?
C10 C11 . 1.365(5) ?
C10 H10 . 0.93 ?
C11 C12 . 1.385(6) ?
C11 H11 . 0.93 ?
C12 C13 . 1.380(6) ?
C12 C14 . 1.501(6) ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 N2 . 1.268(4) ?
C15 O2 . 1.401(4) ?
C16 O3 . 1.191(5) ?
C16 O2 . 1.389(5) ?
C16 C17 . 1.454(6) ?
C17 N2 . 1.433(4) ?
C17 C19 . 1.505(7) ?
C17 C18 . 1.518(7) ?
C18 C19 . 1.472(6) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
N1 H1A . 0.86 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 120.0(4) ?
C6 C1 H1 . . 120.0 ?
C2 C1 H1 . . 120.0 ?
C3 C2 C1 . . 120.3(4) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 120.6(4) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.6(5) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C6 C5 C4 . . 120.5(4) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 119.0(4) ?
C5 C6 C7 . . 123.2(4) ?
C1 C6 C7 . . 117.7(4) ?
O1 C7 N1 . . 123.8(4) ?
O1 C7 C6 . . 121.4(4) ?
N1 C7 C6 . . 114.8(3) ?
C13 C8 N1 . . 122.3(3) ?
C13 C8 C9 . . 118.9(3) ?
N1 C8 C9 . . 118.8(3) ?
C10 C9 C8 . . 118.5(3) ?
C10 C9 C15 . . 119.3(3) ?
C8 C9 C15 . . 122.2(3) ?
C11 C10 C9 . . 121.1(4) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 121.1(4) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C13 C12 C11 . . 118.5(4) ?
C13 C12 C14 . . 120.1(4) ?
C11 C12 C14 . . 121.3(4) ?
C12 C13 C8 . . 121.9(4) ?
C12 C13 H13 . . 119.0 ?
C8 C13 H13 . . 119.0 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N2 C15 O2 . . 115.5(3) ?
N2 C15 C9 . . 129.9(3) ?
O2 C15 C9 . . 114.7(3) ?
O3 C16 O2 . . 120.9(4) ?
O3 C16 C17 . . 133.4(5) ?
O2 C16 C17 . . 105.7(3) ?
N2 C17 C16 . . 107.4(3) ?
N2 C17 C19 . . 122.4(4) ?
C16 C17 C19 . . 120.7(4) ?
N2 C17 C18 . . 121.1(4) ?
C16 C17 C18 . . 120.3(4) ?
C19 C17 C18 . . 58.3(3) ?
C19 C18 C17 . . 60.4(4) ?
C19 C18 H18A . . 117.7 ?
C17 C18 H18A . . 117.7 ?
C19 C18 H18B . . 117.7 ?
C17 C18 H18B . . 117.7 ?
H18A C18 H18B . . 114.8 ?
C18 C19 C17 . . 61.3(4) ?
C18 C19 H19A . . 117.6 ?
C17 C19 H19A . . 117.6 ?
C18 C19 H19B . . 117.6 ?
C17 C19 H19B . . 117.6 ?
H19A C19 H19B . . 114.7 ?
C7 N1 C8 . . 128.6(3) ?
C7 N1 H1A . . 115.7 ?
C8 N1 H1A . . 115.7 ?
C15 N2 C17 . . 105.9(3) ?
C16 O2 C15 . . 105.5(3) ?



####################################################################### 
# 
# 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_yy093
_database_code_depnum_ccdc_archive 'CCDC 2162876'
loop_
_audit_author_name
_audit_author_address
'Youngmee Kim'
;Ewha Womans University
South Korea
;
_audit_update_record             
;
2022-03-29 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            SG-93
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 F3 Ir N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         640.65

_chemical_melting_point          ?

_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                   8.971(2)
_cell_length_b                   27.011(6)
_cell_length_c                   9.490(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.878(7)
_cell_angle_gamma                90
_cell_volume                     2294.3(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9688
_cell_measurement_theta_min      2.7298
_cell_measurement_theta_max      28.4492
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            'light pink'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248

_exptl_absorpt_coefficient_mu    5.874
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            107010
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             5722
_reflns_number_gt                5480
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0560
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.185
_refine_ls_number_reflns         5722
_refine_ls_number_parameters     314
_refine_ls_number_restraints     14
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0143P)²+4.2571P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.903
_refine_diff_density_min         -1.297
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Ir Ir -1.4442 7.9887 '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'

_computing_data_collection       'Bruker Instrument Service v2021.1.0.1'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4610(4) 0.68736(13) 0.1033(4) 0.0397(7) Uani d . . . 1.0 . .
C C2 0.4418(6) 0.65458(18) -0.0244(5) 0.0654(12) Uani d . . . 1.0 . .
H H2A 0.433465 0.670382 -0.116416 0.078 Uiso calc U . R 1.0 . .
H H2B 0.494027 0.623107 -0.021479 0.078 Uiso calc U . R 1.0 . .
C C3 0.3160(5) 0.66054(18) 0.0670(5) 0.0626(11) Uani d . . . 1.0 . .
H H3A 0.291598 0.632736 0.125888 0.075 Uiso calc U . R 1.0 . .
H H3B 0.231019 0.680025 0.030925 0.075 Uiso calc U . R 1.0 . .
C C4 0.4672(4) 0.74139(14) 0.0872(4) 0.0476(9) Uani d . . . 1.0 . .
C C5 0.6206(4) 0.71735(12) 0.2655(4) 0.0379(7) Uani d . . . 1.0 . .
C C6 0.7369(4) 0.71807(13) 0.3752(4) 0.0405(7) Uani d . . . 1.0 . .
C C7 0.7816(4) 0.67003(13) 0.4166(4) 0.0381(7) Uani d . . . 1.0 . .
C C8 0.9013(4) 0.66756(15) 0.5179(4) 0.0486(9) Uani d . . . 1.0 . .
H H8 0.9389 0.636671 0.545068 0.058 Uiso calc U . R 1.0 . .
C C9 0.9668(4) 0.70996(17) 0.5804(4) 0.0521(10) Uani d . . . 1.0 . .
C C10 0.9140(5) 0.75632(17) 0.5394(5) 0.0609(12) Uani d . . . 1.0 . .
H H10 0.955502 0.78443 0.582928 0.073 Uiso calc U . R 1.0 . .
C C11 0.8011(5) 0.76123(15) 0.4354(5) 0.0531(10) Uani d . . . 1.0 . .
H H11 0.767887 0.792361 0.405433 0.064 Uiso calc U . R 1.0 . .
C C12 1.0944(5) 0.7047(2) 0.6917(5) 0.0707(14) Uani d . . . 1.0 . .
H H12A 1.187048 0.711622 0.650584 0.106 Uiso calc U . R 1.0 . .
H H12B 1.096321 0.671525 0.728096 0.106 Uiso calc U . R 1.0 . .
H H12C 1.081005 0.727604 0.767154 0.106 Uiso calc U . R 1.0 . .
C C13 0.5850(4) 0.58401(12) 0.5216(3) 0.0360(7) Uani d . . . 1.0 . .
C C14 0.4596(4) 0.58260(12) 0.4194(4) 0.0371(7) Uani d . . . 1.0 . .
C C15 0.4937(4) 0.54889(12) 0.3080(4) 0.0400(7) Uani d . . . 1.0 . .
C C16 0.6401(4) 0.53120(12) 0.3404(4) 0.0410(8) Uani d . . . 1.0 . .
C C17 0.6990(4) 0.55256(12) 0.4714(4) 0.0396(7) Uani d . . . 1.0 . .
C C18 0.5884(5) 0.61084(14) 0.6595(4) 0.0497(9) Uani d . . . 1.0 . .
H H18A 0.562441 0.588401 0.732388 0.074 Uiso calc U . R 1.0 . .
H H18B 0.517946 0.637634 0.652793 0.074 Uiso calc U . R 1.0 . .
H H18C 0.686861 0.623712 0.6819 0.074 Uiso calc U . R 1.0 . .
C C19 0.3139(4) 0.60842(15) 0.4356(5) 0.0514(9) Uani d . . . 1.0 . .
H H19A 0.265797 0.594203 0.513368 0.077 Uiso calc U . R 1.0 . .
H H19B 0.250726 0.604616 0.350514 0.077 Uiso calc U . R 1.0 . .
H H19C 0.331842 0.642973 0.453253 0.077 Uiso calc U . R 1.0 . .
C C20 0.3899(5) 0.53129(16) 0.1874(5) 0.0587(11) Uani d . . . 1.0 . .
H H20A 0.439498 0.533274 0.101086 0.088 Uiso calc U . R 1.0 . .
H H20B 0.302232 0.551752 0.180403 0.088 Uiso calc U . R 1.0 . .
H H20C 0.361715 0.497599 0.203796 0.088 Uiso calc U . R 1.0 . .
C C21 0.7221(5) 0.49543(15) 0.2531(5) 0.0583(11) Uani d . . . 1.0 . .
H H21A 0.693828 0.462211 0.27541 0.087 Uiso calc U . R 1.0 . .
H H21B 0.827742 0.499419 0.273049 0.087 Uiso calc U . R 1.0 . .
H H21C 0.697267 0.501735 0.154705 0.087 Uiso calc U . R 1.0 . .
C C22 0.8436(5) 0.53827(16) 0.5495(5) 0.0539(10) Uani d . . . 1.0 . .
H H22A 0.860147 0.558812 0.63163 0.081 Uiso calc U . R 1.0 . .
H H22B 0.92412 0.542627 0.489003 0.081 Uiso calc U . R 1.0 . .
H H22C 0.839055 0.504214 0.577894 0.081 Uiso calc U . R 1.0 . .
C C23 0.9071(5) 0.59470(15) 0.1416(4) 0.0477(8) Uani d . . . 1.0 . .
C C24 0.9478(4) 0.58554(12) -0.0109(4) 0.0465(8) Uani d . . D 1.0 . .
F F1 0.9702(18) 0.6279(2) -0.0745(12) 0.073(3) Uani d U P D 0.41(2) A 1
F F1* 0.9055(12) 0.6203(3) -0.1025(6) 0.070(2) Uani d U P D 0.59(2) A 2
F F2 1.0866(4) 0.57198(18) -0.0206(4) 0.1145(14) Uani d . . . 1.0 . .
F F3 0.8704(5) 0.55000(15) -0.0708(4) 0.1172(15) Uani d . . . 1.0 . .
N N1 0.5621(3) 0.67613(10) 0.2223(3) 0.0356(6) Uani d . . . 1.0 . .
O O1 0.4040(4) 0.76866(12) 0.0049(4) 0.0675(9) Uani d . . . 1.0 . .
O O2 0.5674(3) 0.75834(9) 0.1941(3) 0.0493(6) Uani d . . . 1.0 . .
O O3 0.7807(3) 0.61273(10) 0.1458(3) 0.0478(6) Uani d . . . 1.0 . .
O O4 0.9977(4) 0.58236(17) 0.2357(4) 0.0820(11) Uani d . . . 1.0 . .
Ir Ir1 0.65405(2) 0.61300(2) 0.32700(2) 0.03164(4) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.432(4) ?
C1 C4 . 1.469(5) ?
C1 C2 . 1.502(5) ?
C1 C3 . 1.508(6) ?
C2 C3 . 1.478(7) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 O1 . 1.189(5) ?
C4 O2 . 1.387(5) ?
C5 N1 . 1.286(4) ?
C5 O2 . 1.367(4) ?
C5 C6 . 1.424(5) ?
C6 C11 . 1.404(5) ?
C6 C7 . 1.406(5) ?
C7 C8 . 1.394(5) ?
C7 Ir1 . 2.067(3) ?
C8 C9 . 1.401(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.385(7) ?
C9 C12 . 1.511(6) ?
C10 C11 . 1.373(6) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 C17 . 1.435(5) ?
C13 C14 . 1.436(5) ?
C13 C18 . 1.494(5) ?
C13 Ir1 . 2.136(3) ?
C14 C15 . 1.443(5) ?
C14 C19 . 1.499(5) ?
C14 Ir1 . 2.166(3) ?
C15 C16 . 1.412(5) ?
C15 C20 . 1.502(5) ?
C15 Ir1 . 2.251(3) ?
C16 C17 . 1.438(5) ?
C16 C21 . 1.498(5) ?
C16 Ir1 . 2.217(3) ?
C17 C22 . 1.501(5) ?
C17 Ir1 . 2.152(3) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
C23 O4 . 1.213(5) ?
C23 O3 . 1.237(5) ?
C23 C24 . 1.536(5) ?
C24 F3 . 1.294(5) ?
C24 F2 . 1.307(5) ?
C24 F1 . 1.316(2) ?
C24 F1* . 1.318(2) ?
N1 Ir1 . 2.113(3) ?
O3 Ir1 . 2.124(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C4 . . 105.4(3) ?
N1 C1 C2 . . 122.9(3) ?
C4 C1 C2 . . 120.3(3) ?
N1 C1 C3 . . 124.7(3) ?
C4 C1 C3 . . 119.5(3) ?
C2 C1 C3 . . 58.8(3) ?
C3 C2 C1 . . 60.8(3) ?
C3 C2 H2A . . 117.7 ?
C1 C2 H2A . . 117.7 ?
C3 C2 H2B . . 117.7 ?
C1 C2 H2B . . 117.7 ?
H2A C2 H2B . . 114.8 ?
C2 C3 C1 . . 60.4(3) ?
C2 C3 H3A . . 117.7 ?
C1 C3 H3A . . 117.7 ?
C2 C3 H3B . . 117.7 ?
C1 C3 H3B . . 117.7 ?
H3A C3 H3B . . 114.9 ?
O1 C4 O2 . . 122.2(4) ?
O1 C4 C1 . . 131.6(4) ?
O2 C4 C1 . . 106.2(3) ?
N1 C5 O2 . . 115.0(3) ?
N1 C5 C6 . . 120.5(3) ?
O2 C5 C6 . . 124.4(3) ?
C11 C6 C7 . . 123.5(4) ?
C11 C6 C5 . . 124.7(4) ?
C7 C6 C5 . . 111.9(3) ?
C8 C7 C6 . . 115.4(3) ?
C8 C7 Ir1 . . 128.9(3) ?
C6 C7 Ir1 . . 115.7(3) ?
C7 C8 C9 . . 122.3(4) ?
C7 C8 H8 . . 118.8 ?
C9 C8 H8 . . 118.8 ?
C10 C9 C8 . . 119.6(4) ?
C10 C9 C12 . . 120.7(4) ?
C8 C9 C12 . . 119.7(4) ?
C11 C10 C9 . . 120.7(4) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C6 . . 118.3(4) ?
C10 C11 H11 . . 120.8 ?
C6 C11 H11 . . 120.8 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C17 C13 C14 . . 107.7(3) ?
C17 C13 C18 . . 127.2(3) ?
C14 C13 C18 . . 125.0(3) ?
C17 C13 Ir1 . . 71.04(19) ?
C14 C13 Ir1 . . 71.66(19) ?
C18 C13 Ir1 . . 126.1(2) ?
C13 C14 C15 . . 108.5(3) ?
C13 C14 C19 . . 124.6(3) ?
C15 C14 C19 . . 126.7(3) ?
C13 C14 Ir1 . . 69.36(19) ?
C15 C14 Ir1 . . 74.1(2) ?
C19 C14 Ir1 . . 126.7(2) ?
C16 C15 C14 . . 107.1(3) ?
C16 C15 C20 . . 125.3(3) ?
C14 C15 C20 . . 127.3(4) ?
C16 C15 Ir1 . . 70.3(2) ?
C14 C15 Ir1 . . 67.79(18) ?
C20 C15 Ir1 . . 131.6(3) ?
C15 C16 C17 . . 109.6(3) ?
C15 C16 C21 . . 125.6(3) ?
C17 C16 C21 . . 124.9(4) ?
C15 C16 Ir1 . . 72.87(19) ?
C17 C16 Ir1 . . 68.34(19) ?
C21 C16 Ir1 . . 125.4(3) ?
C13 C17 C16 . . 107.2(3) ?
C13 C17 C22 . . 126.9(3) ?
C16 C17 C22 . . 125.3(3) ?
C13 C17 Ir1 . . 69.85(18) ?
C16 C17 Ir1 . . 73.3(2) ?
C22 C17 Ir1 . . 128.9(3) ?
C13 C18 H18A . . 109.5 ?
C13 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C13 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C14 C19 H19A . . 109.5 ?
C14 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C14 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C15 C20 H20A . . 109.5 ?
C15 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C15 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C16 C21 H21A . . 109.5 ?
C16 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C16 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C17 C22 H22A . . 109.5 ?
C17 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C17 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O4 C23 O3 . . 130.8(4) ?
O4 C23 C24 . . 117.3(4) ?
O3 C23 C24 . . 111.8(3) ?
F3 C24 F2 . . 104.3(4) ?
F3 C24 F1 . . 122.6(8) ?
F2 C24 F1 . . 92.1(7) ?
F3 C24 F1* . . 96.7(6) ?
F2 C24 F1* . . 112.7(5) ?
F3 C24 C23 . . 112.2(3) ?
F2 C24 C23 . . 113.6(3) ?
F1 C24 C23 . . 110.2(5) ?
F1* C24 C23 . . 115.5(4) ?
C5 N1 C1 . . 106.9(3) ?
C5 N1 Ir1 . . 114.3(2) ?
C1 N1 Ir1 . . 138.4(2) ?
C5 O2 C4 . . 106.4(3) ?
C23 O3 Ir1 . . 124.7(3) ?
C7 Ir1 N1 . . 77.27(13) ?
C7 Ir1 O3 . . 91.36(12) ?
N1 Ir1 O3 . . 80.53(10) ?
C7 Ir1 C13 . . 95.89(13) ?
N1 Ir1 C13 . . 125.14(12) ?
O3 Ir1 C13 . . 154.28(11) ?
C7 Ir1 C17 . . 103.23(14) ?
N1 Ir1 C17 . . 164.16(12) ?
O3 Ir1 C17 . . 115.18(12) ?
C13 Ir1 C17 . . 39.11(12) ?
C7 Ir1 C14 . . 123.69(13) ?
N1 Ir1 C14 . . 101.34(12) ?
O3 Ir1 C14 . . 144.66(12) ?
C13 Ir1 C14 . . 38.97(13) ?
C17 Ir1 C14 . . 64.91(13) ?
C7 Ir1 C16 . . 138.66(14) ?
N1 Ir1 C16 . . 144.05(12) ?
O3 Ir1 C16 . . 94.51(12) ?
C13 Ir1 C16 . . 64.16(13) ?
C17 Ir1 C16 . . 38.39(13) ?
C14 Ir1 C16 . . 63.18(13) ?
C7 Ir1 C15 . . 159.95(13) ?
N1 Ir1 C15 . . 110.85(12) ?
O3 Ir1 C15 . . 107.85(12) ?
C13 Ir1 C15 . . 64.28(13) ?
C17 Ir1 C15 . . 63.80(13) ?
C14 Ir1 C15 . . 38.09(13) ?
C16 Ir1 C15 . . 36.84(13) ?



