# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_[2]BF4
_database_code_depnum_ccdc_archive 'CCDC 1419539'
loop_
_audit_author_name
_audit_author_address
'Uta Albold'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2019-05-03 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H28 B F4 Ir N2'
_chemical_formula_sum            'C23 H28 B F4 Ir N2'
_chemical_formula_weight         611.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8859(17)
_cell_length_b                   10.6665(19)
_cell_length_c                   11.563(2)
_cell_angle_alpha                86.062(4)
_cell_angle_beta                 72.464(4)
_cell_angle_gamma                89.848(4)
_cell_volume                     1159.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3265
_cell_measurement_theta_min      1.852
_cell_measurement_theta_max      25.063

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    5.801
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5677
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'Blessing, 1995.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart AXS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12766
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.852
_diffrn_reflns_theta_max         25.063
_diffrn_reflns_theta_full        25.063
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4106
_reflns_number_gt                3265
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Smart Software'
_computing_cell_refinement       'Smart Software'
_computing_data_reduction        'Saint + (Bruker, 2009)'
_computing_structure_solution    'intrinsic phasing'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3D, Version 4.0 (Brandenburg, 2014)'
_computing_publication_material  shelxle
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+3.7992P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4106
_refine_ls_number_parameters     301
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.56117(3) 0.64916(3) 0.72852(4) 0.05667(15) Uani 1 1 d . . . . .
N1 N 0.5418(7) 0.4643(5) 0.7537(6) 0.0490(16) Uani 1 1 d . . . . .
H1 H 0.617(8) 0.407(7) 0.750(6) 0.05(2) Uiso 1 1 d . . . . .
N2 N 0.3548(6) 0.6229(6) 0.7633(6) 0.0468(15) Uani 1 1 d . . . . .
C1 C 0.4116(8) 0.4135(7) 0.7808(7) 0.0438(17) Uani 1 1 d . . . . .
C2 C 0.3038(8) 0.5040(7) 0.7861(7) 0.0465(18) Uani 1 1 d . . . . .
C3 C 0.1630(9) 0.4614(8) 0.8139(8) 0.061(2) Uani 1 1 d . . . . .
H3 H 0.0911 0.5188 0.8177 0.073 Uiso 1 1 calc R U . . .
C4 C 0.1310(10) 0.3361(9) 0.8355(9) 0.069(3) Uani 1 1 d . . . . .
H4 H 0.0370 0.3088 0.8549 0.083 Uiso 1 1 calc R U . . .
C5 C 0.2374(9) 0.2482(8) 0.8290(8) 0.060(2) Uani 1 1 d . . . . .
H5 H 0.2129 0.1631 0.8428 0.072 Uiso 1 1 calc R U . . .
C6 C 0.3747(9) 0.2835(7) 0.8031(7) 0.054(2) Uani 1 1 d . . . . .
H6 H 0.4442 0.2238 0.7998 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2578(8) 0.7225(7) 0.7637(10) 0.066(3) Uani 1 1 d . . . . .
C8 C 0.2240(11) 0.7604(10) 0.6597(13) 0.091(4) Uani 1 1 d . . . . .
H8 H 0.2621 0.7213 0.5878 0.109 Uiso 1 1 calc R U . . .
C9 C 0.1303(16) 0.8598(13) 0.666(2) 0.150(8) Uani 1 1 d . . . . .
H9 H 0.1040 0.8863 0.5977 0.180 Uiso 1 1 calc R U . . .
C10 C 0.0771(15) 0.9183(13) 0.770(3) 0.164(11) Uani 1 1 d . . . . .
H10 H 0.0166 0.9855 0.7721 0.197 Uiso 1 1 calc R U . . .
C11 C 0.1109(14) 0.8802(12) 0.873(2) 0.140(7) Uani 1 1 d . . . . .
H11 H 0.0722 0.9213 0.9433 0.168 Uiso 1 1 calc R U . . .
C12 C 0.2034(10) 0.7797(9) 0.8738(13) 0.095(4) Uani 1 1 d . . . . .
H12 H 0.2271 0.7528 0.9434 0.114 Uiso 1 1 calc R U . . .
C13A C 0.481(3) 0.610(2) 0.945(2) 0.089(6) Uiso 0.5 1 d . . P A 1
H13A H 0.5605 0.6141 0.9758 0.134 Uiso 0.5 1 calc R U P A 1
H13B H 0.4138 0.6727 0.9795 0.134 Uiso 0.5 1 calc R U P A 1
H13C H 0.4367 0.5284 0.9652 0.134 Uiso 0.5 1 calc R U P A 1
C13B C 0.554(2) 0.586(2) 0.5378(18) 0.077(5) Uiso 0.5 1 d . . P A 2
H13D H 0.6491 0.5859 0.4830 0.116 Uiso 0.5 1 calc R U P A 2
H13E H 0.5128 0.5035 0.5481 0.116 Uiso 0.5 1 calc R U P A 2
H13F H 0.4985 0.6442 0.5051 0.116 Uiso 0.5 1 calc R U P A 2
C20 C 0.6146(8) 0.8513(6) 0.6848(7) 0.0464(18) Uani 1 1 d . . . . .
C21 C 0.6468(9) 0.8105(7) 0.7941(8) 0.056(2) Uani 1 1 d . . . . .
C22 C 0.7480(8) 0.7128(7) 0.7696(8) 0.052(2) Uani 1 1 d . . . . .
C23 C 0.7829(8) 0.6963(7) 0.6451(9) 0.059(2) Uani 1 1 d . . . . .
C24 C 0.7002(12) 0.7818(8) 0.5919(9) 0.073(3) Uani 1 1 d . . . . .
C25 C 0.713(3) 0.8008(17) 0.4627(12) 0.197(11) Uani 1 1 d . . . . .
H25A H 0.7612 0.7313 0.4209 0.296 Uiso 1 1 calc R U . . .
H25B H 0.7655 0.8772 0.4294 0.296 Uiso 1 1 calc R U . . .
H25C H 0.6198 0.8066 0.4530 0.296 Uiso 1 1 calc R U . . .
C26 C 0.8924(13) 0.6095(11) 0.5755(12) 0.106(4) Uani 1 1 d . . . . .
H26A H 0.8635 0.5800 0.5098 0.160 Uiso 1 1 calc R U . . .
H26B H 0.9021 0.5392 0.6287 0.160 Uiso 1 1 calc R U . . .
H26C H 0.9818 0.6537 0.5434 0.160 Uiso 1 1 calc R U . . .
C27 C 0.8144(12) 0.6478(10) 0.8564(11) 0.087(3) Uani 1 1 d . . . . .
H27A H 0.8297 0.5614 0.8383 0.131 Uiso 1 1 calc R U . . .
H27B H 0.7527 0.6518 0.9379 0.131 Uiso 1 1 calc R U . . .
H27C H 0.9037 0.6881 0.8489 0.131 Uiso 1 1 calc R U . . .
C28 C 0.5897(18) 0.8693(13) 0.9117(11) 0.126(6) Uani 1 1 d . . . . .
H28A H 0.6618 0.9220 0.9244 0.190 Uiso 1 1 calc R U . . .
H28B H 0.5612 0.8048 0.9768 0.190 Uiso 1 1 calc R U . . .
H28C H 0.5093 0.9190 0.9097 0.190 Uiso 1 1 calc R U . . .
C29 C 0.5187(10) 0.9564(7) 0.6721(10) 0.069(3) Uani 1 1 d . . . . .
H29A H 0.5740 1.0322 0.6422 0.104 Uiso 1 1 calc R U . . .
H29B H 0.4516 0.9684 0.7499 0.104 Uiso 1 1 calc R U . . .
H29C H 0.4689 0.9362 0.6160 0.104 Uiso 1 1 calc R U . . .
B1 B 0.8024(8) 0.2140(7) 0.7419(9) 0.090(4) Uani 1 1 d D . . . .
F4A F 0.7315(16) 0.2304(16) 0.6542(14) 0.132(4) Uani 0.512(9) 1 d D . P B 3
F3A F 0.794(4) 0.3269(11) 0.798(2) 0.113(8) Uani 0.512(9) 1 d D . P B 3
F2A F 0.9423(15) 0.180(3) 0.688(2) 0.150(8) Uani 0.512(9) 1 d D . P B 3
F1A F 0.7155(18) 0.1253(15) 0.8254(15) 0.142(5) Uani 0.512(9) 1 d D . P B 3
F3 F 0.818(4) 0.3437(9) 0.744(3) 0.113(8) Uani 0.488(9) 1 d D . P B 4
F4 F 0.6626(10) 0.1694(18) 0.7744(19) 0.132(4) Uani 0.488(9) 1 d D . P B 4
F2 F 0.906(2) 0.171(4) 0.6424(16) 0.150(8) Uani 0.488(9) 1 d D . P B 4
F1 F 0.840(2) 0.1568(16) 0.8397(14) 0.142(5) Uani 0.488(9) 1 d D . P B 4


_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 N2 1.974(6) . ?
Ir1 N1 1.975(6) . ?
Ir1 C23 2.157(8) . ?
Ir1 C22 2.163(8) . ?
Ir1 C24 2.187(9) . ?
Ir1 C21 2.197(8) . ?
Ir1 C20 2.209(7) . ?
Ir1 C13B 2.368(19) . ?
Ir1 C13A 2.39(2) . ?
N1 C1 1.336(9) . ?
N2 C2 1.345(9) . ?
N2 C7 1.428(9) . ?
C1 C6 1.421(10) . ?
C1 C2 1.426(10) . ?
C2 C3 1.400(11) . ?
C3 C4 1.363(13) . ?
C4 C5 1.396(13) . ?
C5 C6 1.348(12) . ?
C7 C8 1.378(15) . ?
C7 C12 1.405(16) . ?
C8 C9 1.397(17) . ?
C9 C10 1.36(3) . ?
C10 C11 1.36(3) . ?
C11 C12 1.409(17) . ?
C20 C24 1.406(12) . ?
C20 C21 1.434(12) . ?
C20 C29 1.494(10) . ?
C21 C22 1.426(10) . ?
C21 C28 1.487(14) . ?
C22 C23 1.399(13) . ?
C22 C27 1.489(12) . ?
C23 C24 1.450(13) . ?
C23 C26 1.500(12) . ?
C24 C25 1.461(16) . ?
B1 F2A 1.394(2) . ?
B1 F4 1.394(2) . ?
B1 F1A 1.394(2) . ?
B1 F2 1.395(2) . ?
B1 F3 1.395(2) . ?
B1 F3A 1.395(2) . ?
B1 F4A 1.398(2) . ?
B1 F1 1.398(2) . ?

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 N1 78.0(2) . . ?
N2 Ir1 C23 165.1(3) . . ?
N1 Ir1 C23 108.0(3) . . ?
N2 Ir1 C22 153.8(3) . . ?
N1 Ir1 C22 110.3(3) . . ?
C23 Ir1 C22 37.8(3) . . ?
N2 Ir1 C24 127.7(3) . . ?
N1 Ir1 C24 135.3(3) . . ?
C23 Ir1 C24 39.0(4) . . ?
C22 Ir1 C24 64.3(4) . . ?
N2 Ir1 C21 121.2(3) . . ?
N1 Ir1 C21 141.1(3) . . ?
C23 Ir1 C21 62.8(3) . . ?
C22 Ir1 C21 38.2(3) . . ?
C24 Ir1 C21 62.7(4) . . ?
N2 Ir1 C20 109.5(3) . . ?
N1 Ir1 C20 171.8(3) . . ?
C23 Ir1 C20 63.9(3) . . ?
C22 Ir1 C20 64.6(3) . . ?
C24 Ir1 C20 37.3(3) . . ?
C21 Ir1 C20 38.0(3) . . ?
N2 Ir1 C13B 80.0(6) . . ?
N1 Ir1 C13B 76.4(6) . . ?
C23 Ir1 C13B 88.1(6) . . ?
C22 Ir1 C13B 125.7(6) . . ?
C24 Ir1 C13B 74.1(6) . . ?
C21 Ir1 C13B 136.2(6) . . ?
C20 Ir1 C13B 101.1(6) . . ?
N2 Ir1 C13A 77.2(6) . . ?
N1 Ir1 C13A 76.0(6) . . ?
C23 Ir1 C13A 117.3(6) . . ?
C22 Ir1 C13A 80.9(6) . . ?
C24 Ir1 C13A 138.7(7) . . ?
C21 Ir1 C13A 76.4(6) . . ?
C20 Ir1 C13A 108.5(6) . . ?
C1 N1 Ir1 117.7(5) . . ?
C2 N2 C7 118.6(6) . . ?
C2 N2 Ir1 117.7(5) . . ?
C7 N2 Ir1 123.7(5) . . ?
N1 C1 C6 126.6(7) . . ?
N1 C1 C2 113.5(6) . . ?
C6 C1 C2 119.9(7) . . ?
N2 C2 C3 128.5(7) . . ?
N2 C2 C1 113.0(6) . . ?
C3 C2 C1 118.5(7) . . ?
C4 C3 C2 120.3(8) . . ?
C3 C4 C5 120.8(8) . . ?
C6 C5 C4 121.6(8) . . ?
C5 C6 C1 118.9(8) . . ?
C8 C7 C12 123.0(9) . . ?
C8 C7 N2 120.6(9) . . ?
C12 C7 N2 116.4(9) . . ?
C7 C8 C9 117.6(15) . . ?
C10 C9 C8 121.0(18) . . ?
C9 C10 C11 121.0(12) . . ?
C10 C11 C12 121.3(17) . . ?
C7 C12 C11 116.1(15) . . ?
C24 C20 C21 106.7(7) . . ?
C24 C20 C29 127.4(8) . . ?
C21 C20 C29 125.6(7) . . ?
C24 C20 Ir1 70.5(5) . . ?
C21 C20 Ir1 70.6(4) . . ?
C29 C20 Ir1 128.3(6) . . ?
C22 C21 C20 109.5(7) . . ?
C22 C21 C28 126.2(8) . . ?
C20 C21 C28 124.1(8) . . ?
C22 C21 Ir1 69.6(4) . . ?
C20 C21 Ir1 71.5(4) . . ?
C28 C21 Ir1 128.7(9) . . ?
C23 C22 C21 106.9(7) . . ?
C23 C22 C27 125.9(8) . . ?
C21 C22 C27 127.1(9) . . ?
C23 C22 Ir1 70.9(5) . . ?
C21 C22 Ir1 72.2(5) . . ?
C27 C22 Ir1 126.0(6) . . ?
C22 C23 C24 108.8(7) . . ?
C22 C23 C26 126.3(9) . . ?
C24 C23 C26 124.9(10) . . ?
C22 C23 Ir1 71.4(4) . . ?
C24 C23 Ir1 71.6(5) . . ?
C26 C23 Ir1 125.3(7) . . ?
C20 C24 C23 108.0(8) . . ?
C20 C24 C25 125.7(10) . . ?
C23 C24 C25 126.0(10) . . ?
C20 C24 Ir1 72.2(5) . . ?
C23 C24 Ir1 69.4(5) . . ?
C25 C24 Ir1 128.2(12) . . ?
F2A B1 F1A 116.7(17) . . ?
F4 B1 F2 121.3(18) . . ?
F4 B1 F3 115.2(19) . . ?
F2 B1 F3 109.7(19) . . ?
F2A B1 F3A 111.9(18) . . ?
F1A B1 F3A 108.1(15) . . ?
F2A B1 F4A 110.1(14) . . ?
F1A B1 F4A 102.0(11) . . ?
F3A B1 F4A 107.2(15) . . ?
F4 B1 F1 98.3(11) . . ?
F2 B1 F1 102.0(14) . . ?
F3 B1 F1 107.7(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ir1 N1 C1 C6 -179.6(6) . . . . ?
Ir1 N1 C1 C2 0.7(9) . . . . ?
C7 N2 C2 C3 -1.5(13) . . . . ?
Ir1 N2 C2 C3 179.4(7) . . . . ?
C7 N2 C2 C1 178.9(7) . . . . ?
Ir1 N2 C2 C1 -0.2(9) . . . . ?
N1 C1 C2 N2 -0.3(10) . . . . ?
C6 C1 C2 N2 179.9(7) . . . . ?
N1 C1 C2 C3 -180.0(7) . . . . ?
C6 C1 C2 C3 0.3(12) . . . . ?
N2 C2 C3 C4 -179.4(9) . . . . ?
C1 C2 C3 C4 0.1(13) . . . . ?
C2 C3 C4 C5 -0.8(15) . . . . ?
C3 C4 C5 C6 1.0(15) . . . . ?
C4 C5 C6 C1 -0.6(13) . . . . ?
N1 C1 C6 C5 -179.8(8) . . . . ?
C2 C1 C6 C5 0.0(12) . . . . ?
C2 N2 C7 C8 -87.6(10) . . . . ?
Ir1 N2 C7 C8 91.4(10) . . . . ?
C2 N2 C7 C12 93.9(10) . . . . ?
Ir1 N2 C7 C12 -87.1(9) . . . . ?
C12 C7 C8 C9 -0.5(15) . . . . ?
N2 C7 C8 C9 -178.9(9) . . . . ?
C7 C8 C9 C10 1.3(19) . . . . ?
C8 C9 C10 C11 -1(2) . . . . ?
C9 C10 C11 C12 1(2) . . . . ?
C8 C7 C12 C11 -0.2(15) . . . . ?
N2 C7 C12 C11 178.3(9) . . . . ?
C10 C11 C12 C7 0.1(19) . . . . ?
C24 C20 C21 C22 -2.2(10) . . . . ?
C29 C20 C21 C22 -176.8(8) . . . . ?
Ir1 C20 C21 C22 59.4(6) . . . . ?
C24 C20 C21 C28 173.7(11) . . . . ?
C29 C20 C21 C28 -0.9(15) . . . . ?
Ir1 C20 C21 C28 -124.7(11) . . . . ?
C24 C20 C21 Ir1 -61.6(6) . . . . ?
C29 C20 C21 Ir1 123.8(8) . . . . ?
C20 C21 C22 C23 2.3(9) . . . . ?
C28 C21 C22 C23 -173.5(11) . . . . ?
Ir1 C21 C22 C23 62.8(5) . . . . ?
C20 C21 C22 C27 177.4(9) . . . . ?
C28 C21 C22 C27 1.6(16) . . . . ?
Ir1 C21 C22 C27 -122.1(9) . . . . ?
C20 C21 C22 Ir1 -60.6(6) . . . . ?
C28 C21 C22 Ir1 123.7(12) . . . . ?
C21 C22 C23 C24 -1.5(9) . . . . ?
C27 C22 C23 C24 -176.7(9) . . . . ?
Ir1 C22 C23 C24 62.2(6) . . . . ?
C21 C22 C23 C26 175.7(9) . . . . ?
C27 C22 C23 C26 0.5(15) . . . . ?
Ir1 C22 C23 C26 -120.6(10) . . . . ?
C21 C22 C23 Ir1 -63.7(6) . . . . ?
C27 C22 C23 Ir1 121.1(9) . . . . ?
C21 C20 C24 C23 1.2(10) . . . . ?
C29 C20 C24 C23 175.7(8) . . . . ?
Ir1 C20 C24 C23 -60.4(6) . . . . ?
C21 C20 C24 C25 -173.7(15) . . . . ?
C29 C20 C24 C25 1(2) . . . . ?
Ir1 C20 C24 C25 124.6(16) . . . . ?
C21 C20 C24 Ir1 61.6(6) . . . . ?
C29 C20 C24 Ir1 -123.9(8) . . . . ?
C22 C23 C24 C20 0.2(10) . . . . ?
C26 C23 C24 C20 -177.1(9) . . . . ?
Ir1 C23 C24 C20 62.2(7) . . . . ?
C22 C23 C24 C25 175.1(15) . . . . ?
C26 C23 C24 C25 -2(2) . . . . ?
Ir1 C23 C24 C25 -122.9(16) . . . . ?
C22 C23 C24 Ir1 -62.0(6) . . . . ?
C26 C23 C24 Ir1 120.7(10) . . . . ?

_refine_diff_density_max         1.450
_refine_diff_density_min         -1.246
_refine_diff_density_rms         0.131

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1882360'
loop_
_audit_author_name
_audit_author_address
'Uta Albold'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 Ir N2'
_chemical_formula_weight         509.64

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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4919(3)
_cell_length_b                   11.4836(4)
_cell_length_c                   15.7162(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.245(2)
_cell_angle_gamma                90
_cell_volume                     1893.55(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4235
_cell_measurement_theta_min      2.592
_cell_measurement_theta_max      28.754

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    7.057
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5678
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19851
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.592
_diffrn_reflns_theta_max         28.754
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4911
_reflns_number_gt                4235
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'Saint + (Bruker, 2009)'
_computing_structure_solution    'intrinsic phasing'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3D, Version 4.0 (Brandenburg, 2014)'
_computing_publication_material  shelxle
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0123P)²+2.1572P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4911
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0432
_refine_ls_wR_factor_gt          0.0411
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.74489(2) 0.46359(2) 0.41784(2) 0.01041(4) Uani 1 1 d . . . . .
C1 C 0.7703(3) 0.7136(2) 0.41125(19) 0.0128(6) Uani 1 1 d . . . . .
N1 N 0.7651(2) 0.6203(2) 0.46556(16) 0.0135(5) Uani 1 1 d . . . . .
H1 H 0.770(3) 0.633(3) 0.517(2) 0.012(9) Uiso 1 1 d . . . . .
N2 N 0.7428(2) 0.5628(2) 0.31432(15) 0.0125(5) Uani 1 1 d . . . . .
C2 C 0.7576(3) 0.6810(2) 0.32498(19) 0.0134(6) Uani 1 1 d . . . . .
C5 C 0.7934(3) 0.9143(3) 0.3696(2) 0.0232(7) Uani 1 1 d . . . . .
H5 H 0.8064 0.9938 0.3840 0.028 Uiso 1 1 calc R U . . .
C4 C 0.7809(3) 0.8821(3) 0.2843(2) 0.0217(7) Uani 1 1 d . . . . .
H4 H 0.7845 0.9401 0.2412 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7869(3) 0.8311(3) 0.4336(2) 0.0188(6) Uani 1 1 d . . . . .
H6 H 0.7936 0.8533 0.4916 0.023 Uiso 1 1 calc R U . . .
C3 C 0.7632(3) 0.7668(2) 0.26171(19) 0.0166(6) Uani 1 1 d . . . . .
H3 H 0.7549 0.7458 0.2035 0.020 Uiso 1 1 calc R U . . .
C7 C 0.7229(3) 0.5195(2) 0.23051(18) 0.0153(6) Uani 1 1 d . . . . .
C8 C 0.5998(3) 0.5031(3) 0.1997(2) 0.0208(7) Uani 1 1 d . . . . .
H8 H 0.5290 0.5214 0.2347 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5792(4) 0.4602(3) 0.1183(2) 0.0306(8) Uani 1 1 d . . . . .
H9 H 0.4949 0.4488 0.0976 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6831(4) 0.4343(3) 0.0674(2) 0.0313(9) Uani 1 1 d . . . . .
H10 H 0.6696 0.4069 0.0111 0.038 Uiso 1 1 calc R U . . .
C11 C 0.8059(4) 0.4479(3) 0.0977(2) 0.0335(9) Uani 1 1 d . . . . .
H11 H 0.8764 0.4275 0.0630 0.040 Uiso 1 1 calc R U . . .
C12 C 0.8259(3) 0.4914(3) 0.1789(2) 0.0208(7) Uani 1 1 d . . . . .
H12 H 0.9104 0.5021 0.1995 0.025 Uiso 1 1 calc R U . . .
C13 C 0.8085(3) 0.3382(2) 0.51162(18) 0.0133(6) Uani 1 1 d . . . . .
C14 C 0.6726(3) 0.3449(2) 0.51344(18) 0.0130(6) Uani 1 1 d . . . . .
C15 C 0.6244(3) 0.3112(2) 0.42993(18) 0.0135(6) Uani 1 1 d . . . . .
C16 C 0.7305(3) 0.2810(2) 0.37764(19) 0.0159(6) Uani 1 1 d . . . . .
C17 C 0.8448(3) 0.2991(3) 0.42690(19) 0.0150(6) Uani 1 1 d . . . . .
C18 C 0.8979(3) 0.3621(3) 0.58385(19) 0.0175(6) Uani 1 1 d . . . . .
H18A H 0.9187 0.2889 0.6128 0.026 Uiso 1 1 calc R U . . .
H18B H 0.8574 0.4156 0.6241 0.026 Uiso 1 1 calc R U . . .
H18C H 0.9762 0.3975 0.5619 0.026 Uiso 1 1 calc R U . . .
C19 C 0.5910(3) 0.3752(3) 0.58820(18) 0.0162(6) Uani 1 1 d . . . . .
H19A H 0.5650 0.3037 0.6174 0.024 Uiso 1 1 calc R U . . .
H19B H 0.5151 0.4172 0.5685 0.024 Uiso 1 1 calc R U . . .
H19C H 0.6395 0.4245 0.6276 0.024 Uiso 1 1 calc R U . . .
C20 C 0.4872(3) 0.3015(3) 0.4055(2) 0.0209(7) Uani 1 1 d . . . . .
H20A H 0.4559 0.2235 0.4197 0.031 Uiso 1 1 calc R U . . .
H20B H 0.4779 0.3148 0.3442 0.031 Uiso 1 1 calc R U . . .
H20C H 0.4378 0.3599 0.4367 0.031 Uiso 1 1 calc R U . . .
C21 C 0.7229(3) 0.2338(3) 0.2890(2) 0.0218(7) Uani 1 1 d . . . . .
H21A H 0.7107 0.1492 0.2912 0.033 Uiso 1 1 calc R U . . .
H21B H 0.8021 0.2514 0.2588 0.033 Uiso 1 1 calc R U . . .
H21C H 0.6509 0.2697 0.2590 0.033 Uiso 1 1 calc R U . . .
C22 C 0.9776(3) 0.2774(3) 0.3968(2) 0.0232(7) Uani 1 1 d . . . . .
H22A H 1.0023 0.1972 0.4106 0.035 Uiso 1 1 calc R U . . .
H22B H 1.0361 0.3317 0.4250 0.035 Uiso 1 1 calc R U . . .
H22C H 0.9815 0.2888 0.3351 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N1 1.961(2) . ?
Ir1 N2 1.986(2) . ?
Ir1 C13 2.164(3) . ?
Ir1 C17 2.164(3) . ?
Ir1 C15 2.168(3) . ?
Ir1 C14 2.168(3) . ?
Ir1 C16 2.195(3) . ?
C1 N1 1.371(4) . ?
C1 C6 1.404(4) . ?
C1 C2 1.412(4) . ?
N1 H1 0.83(3) . ?
N2 C2 1.377(4) . ?
N2 C7 1.422(4) . ?
C2 C3 1.401(4) . ?
C5 C6 1.389(4) . ?
C5 C4 1.396(5) . ?
C5 H5 0.9500 . ?
C4 C3 1.383(4) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C7 C8 1.391(5) . ?
C7 C12 1.391(4) . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.429(4) . ?
C13 C17 1.457(4) . ?
C13 C18 1.495(4) . ?
C14 C15 1.457(4) . ?
C14 C19 1.497(4) . ?
C15 C16 1.429(4) . ?
C15 C20 1.492(4) . ?
C16 C17 1.440(4) . ?
C16 C21 1.497(4) . ?
C17 C22 1.494(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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 N2 77.74(10) . . ?
N1 Ir1 C13 108.52(11) . . ?
N2 Ir1 C13 160.38(11) . . ?
N1 Ir1 C17 136.39(11) . . ?
N2 Ir1 C17 123.92(10) . . ?
C13 Ir1 C17 39.35(11) . . ?
N1 Ir1 C15 140.32(11) . . ?
N2 Ir1 C15 122.03(10) . . ?
C13 Ir1 C15 65.25(11) . . ?
C17 Ir1 C15 64.68(11) . . ?
N1 Ir1 C14 110.46(11) . . ?
N2 Ir1 C14 157.74(11) . . ?
C13 Ir1 C14 38.51(11) . . ?
C17 Ir1 C14 64.96(11) . . ?
C15 Ir1 C14 39.26(11) . . ?
N1 Ir1 C16 173.75(11) . . ?
N2 Ir1 C16 108.16(10) . . ?
C13 Ir1 C16 65.23(11) . . ?
C17 Ir1 C16 38.57(11) . . ?
C15 Ir1 C16 38.24(11) . . ?
C14 Ir1 C16 64.86(11) . . ?
N1 C1 C6 126.9(3) . . ?
N1 C1 C2 112.7(2) . . ?
C6 C1 C2 120.4(3) . . ?
C1 N1 Ir1 118.9(2) . . ?
C1 N1 H1 118(2) . . ?
Ir1 N1 H1 123(2) . . ?
C2 N2 C7 118.2(2) . . ?
C2 N2 Ir1 117.71(19) . . ?
C7 N2 Ir1 124.02(18) . . ?
N2 C2 C3 127.7(3) . . ?
N2 C2 C1 112.9(3) . . ?
C3 C2 C1 119.4(3) . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C8 C7 C12 119.2(3) . . ?
C8 C7 N2 120.1(3) . . ?
C12 C7 N2 120.7(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 120.4(4) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C17 107.5(3) . . ?
C14 C13 C18 126.7(3) . . ?
C17 C13 C18 125.8(3) . . ?
C14 C13 Ir1 70.90(16) . . ?
C17 C13 Ir1 70.34(16) . . ?
C18 C13 Ir1 125.8(2) . . ?
C13 C14 C15 108.1(2) . . ?
C13 C14 C19 127.0(3) . . ?
C15 C14 C19 124.9(3) . . ?
C13 C14 Ir1 70.59(16) . . ?
C15 C14 Ir1 70.36(15) . . ?
C19 C14 Ir1 126.9(2) . . ?
C16 C15 C14 108.3(3) . . ?
C16 C15 C20 125.9(3) . . ?
C14 C15 C20 125.6(3) . . ?
C16 C15 Ir1 71.92(16) . . ?
C14 C15 Ir1 70.38(16) . . ?
C20 C15 Ir1 126.8(2) . . ?
C15 C16 C17 107.7(3) . . ?
C15 C16 C21 125.8(3) . . ?
C17 C16 C21 126.4(3) . . ?
C15 C16 Ir1 69.85(16) . . ?
C17 C16 Ir1 69.56(16) . . ?
C21 C16 Ir1 128.1(2) . . ?
C16 C17 C13 108.4(3) . . ?
C16 C17 C22 125.5(3) . . ?
C13 C17 C22 126.0(3) . . ?
C16 C17 Ir1 71.87(16) . . ?
C13 C17 Ir1 70.31(16) . . ?
C22 C17 Ir1 125.3(2) . . ?
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 . . ?

_refine_diff_density_max         1.373
_refine_diff_density_min         -1.379
_refine_diff_density_rms         0.131

####################################################################### 
# 
# 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_[3]OTf
_database_code_depnum_ccdc_archive 'CCDC 1429223'
loop_
_audit_author_name
_audit_author_address
'Margarethe van der Meer'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2019-05-03 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H25 Cl F3 Ir N2 O3 S'
_chemical_formula_sum            'C23 H25 Cl F3 Ir N2 O3 S'
_chemical_formula_weight         694.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.743(8)
_cell_length_b                   11.872(5)
_cell_length_c                   28.358(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.077(15)
_cell_angle_gamma                90
_cell_volume                     4936(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    189(2)
_cell_measurement_reflns_used    8348
_cell_measurement_theta_min      2.207
_cell_measurement_theta_max      26.392

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_F_000             2704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    5.654
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5511
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      189(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67206
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.207
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10057
_reflns_number_gt                8348
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX 2 (Bruker, 2012)'
_computing_cell_refinement       'APEX 2 (Bruker, 2012)'
_computing_data_reduction        'Saint + (Bruker, 2009)'
_computing_structure_solution    'intrinsic phasing'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3D, Version 4.0 (Brandenburg, 2014)'
_computing_publication_material  shelxle
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+2.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10057
_refine_ls_number_parameters     631
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0380
_refine_ls_wR_factor_gt          0.0358
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_restrained_S_all      1.234
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1A Ir 0.15500(2) -0.31654(2) 0.63341(2) 0.01367(3) Uani 1 1 d . . . . .
Ir1 Ir 0.35243(2) 0.18587(2) 0.61780(2) 0.01248(3) Uani 1 1 d . . . . .
Cl1A Cl 0.19991(5) -0.12354(6) 0.63486(3) 0.02256(17) Uani 1 1 d . . . . .
S1A S 0.23686(5) 0.20723(6) 0.78849(2) 0.02118(17) Uani 1 1 d . . . . .
S1 S 0.21457(6) -0.17089(6) 0.94604(3) 0.02549(18) Uani 1 1 d . . . . .
Cl1 Cl 0.30078(5) 0.37463(6) 0.60489(2) 0.02050(16) Uani 1 1 d . . . . .
C20 C 0.45412(19) 0.0923(2) 0.66202(9) 0.0179(6) Uani 1 1 d . . . . .
C23A C 0.0474(2) -0.4276(2) 0.60339(10) 0.0201(7) Uani 1 1 d . . . . .
F2A F 0.29178(14) 0.00141(16) 0.81045(7) 0.0415(5) Uani 1 1 d . . . . .
C28 C 0.5268(2) 0.3587(3) 0.60416(11) 0.0262(7) Uani 1 1 d . . . . .
H28A H 0.5120 0.3706 0.5700 0.039 Uiso 1 1 calc R U . . .
H28B H 0.5928 0.3653 0.6123 0.039 Uiso 1 1 calc R U . . .
H28C H 0.4956 0.4155 0.6216 0.039 Uiso 1 1 calc R U . . .
F3 F 0.29098(13) 0.01020(15) 0.91319(7) 0.0388(5) Uani 1 1 d . . . . .
C9 C 0.2802(2) 0.1957(2) 0.44468(9) 0.0205(7) Uani 1 1 d . . . . .
H9 H 0.2919 0.2583 0.4254 0.025 Uiso 1 1 calc R U . . .
C27A C -0.0181(2) -0.1522(3) 0.65753(12) 0.0295(8) Uani 1 1 d . . . . .
H27A H -0.0848 -0.1517 0.6562 0.044 Uiso 1 1 calc R U . . .
H27B H 0.0013 -0.0984 0.6344 0.044 Uiso 1 1 calc R U . . .
H27C H 0.0084 -0.1307 0.6894 0.044 Uiso 1 1 calc R U . . .
F2 F 0.16249(14) 0.04143(17) 0.93896(7) 0.0470(5) Uani 1 1 d . . . . .
C7A C 0.2863(2) -0.3602(2) 0.72328(10) 0.0184(6) Uani 1 1 d . . . . .
C2 C 0.1652(2) 0.1519(2) 0.63597(9) 0.0135(6) Uani 1 1 d . . . . .
F1 F 0.28066(16) 0.01051(16) 0.98826(7) 0.0486(6) Uani 1 1 d . . . . .
O3 O 0.30421(17) -0.21921(19) 0.95424(9) 0.0444(7) Uani 1 1 d . . . . .
F3A F 0.18418(15) 0.01166(16) 0.75255(7) 0.0471(6) Uani 1 1 d . . . . .
O1A O 0.14989(15) 0.25066(17) 0.76849(7) 0.0290(5) Uani 1 1 d . . . . .
C8A C 0.2663(2) -0.2675(3) 0.75071(10) 0.0226(7) Uani 1 1 d . . . . .
H8A H 0.2504 -0.1971 0.7362 0.027 Uiso 1 1 calc R U . . .
C4A C 0.4884(2) -0.3497(2) 0.58776(11) 0.0232(7) Uani 1 1 d . . . . .
H4A H 0.5365 -0.3510 0.5680 0.028 Uiso 1 1 calc R U . . .
O3A O 0.26827(16) 0.24305(18) 0.83579(7) 0.0305(6) Uani 1 1 d . . . . .
F1A F 0.15341(14) 0.03668(17) 0.82443(7) 0.0461(5) Uani 1 1 d . . . . .
O1 O 0.16086(15) -0.18355(19) 0.98563(7) 0.0327(5) Uani 1 1 d . . . . .
C1 C 0.1636(2) 0.1324(2) 0.58467(9) 0.0137(6) Uani 1 1 d . . . . .
C10 C 0.2705(2) 0.0892(3) 0.42492(10) 0.0239(7) Uani 1 1 d . . . . .
H10 H 0.2754 0.0791 0.3921 0.029 Uiso 1 1 calc R U . . .
N2 N 0.24540(16) 0.13657(18) 0.56957(7) 0.0138(5) Uani 1 1 d . . . . .
C22 C 0.4963(2) 0.2442(2) 0.61711(10) 0.0161(7) Uani 1 1 d . . . . .
C3 C 0.0817(2) 0.1538(2) 0.65711(10) 0.0190(7) Uani 1 1 d . . . . .
H3 H 0.0817 0.1646 0.6903 0.023 Uiso 1 1 calc R U . . .
C22A C 0.0672(2) -0.4516(2) 0.65287(10) 0.0186(6) Uani 1 1 d . . . . .
N1A N 0.27807(16) -0.34835(18) 0.67239(8) 0.0157(5) Uani 1 1 d . . . . .
O2 O 0.16746(18) -0.1905(2) 0.90085(8) 0.0473(7) Uani 1 1 d . . . . .
N1 N 0.24737(16) 0.16878(19) 0.65723(8) 0.0143(5) Uani 1 1 d . . . . .
C6 C 0.0774(2) 0.1155(2) 0.55714(10) 0.0198(7) Uani 1 1 d . . . . .
H6 H 0.0745 0.1009 0.5241 0.024 Uiso 1 1 calc R U . . .
C20A C 0.0137(2) -0.2678(2) 0.64618(11) 0.0204(7) Uani 1 1 d . . . . .
C24A C 0.0566(2) -0.5091(3) 0.56410(10) 0.0296(8) Uani 1 1 d . . . . .
H24A H 0.0615 -0.4678 0.5346 0.044 Uiso 1 1 calc R U . . .
H24B H 0.0030 -0.5583 0.5602 0.044 Uiso 1 1 calc R U . . .
H24C H 0.1116 -0.5549 0.5718 0.044 Uiso 1 1 calc R U . . .
C23 C 0.4803(2) 0.1505(2) 0.58574(9) 0.0164(6) Uani 1 1 d . . . . .
C9A C 0.2700(2) -0.2803(3) 0.79954(10) 0.0282(8) Uani 1 1 d . . . . .
H9A H 0.2569 -0.2181 0.8188 0.034 Uiso 1 1 calc R U . . .
O2A O 0.30652(15) 0.2083(2) 0.75598(7) 0.0320(6) Uani 1 1 d . . . . .
C27 C 0.4894(2) 0.2852(3) 0.70714(10) 0.0256(7) Uani 1 1 d . . . . .
H27D H 0.5530 0.2816 0.7213 0.038 Uiso 1 1 calc R U . . .
H27E H 0.4491 0.2597 0.7303 0.038 Uiso 1 1 calc R U . . .
H27F H 0.4742 0.3629 0.6978 0.038 Uiso 1 1 calc R U . . .
C21A C 0.0466(2) -0.3521(2) 0.67980(10) 0.0185(7) Uani 1 1 d . . . . .
C4 C 0.0028(2) 0.1399(2) 0.62933(10) 0.0235(7) Uani 1 1 d . . . . .
H4 H -0.0530 0.1429 0.6432 0.028 Uiso 1 1 calc R U . . .
C10A C 0.2927(2) -0.3834(3) 0.82024(10) 0.0309(8) Uani 1 1 d . . . . .
H10A H 0.2948 -0.3914 0.8537 0.037 Uiso 1 1 calc R U . . .
C21 C 0.47729(19) 0.2106(2) 0.66419(9) 0.0174(6) Uani 1 1 d . . . . .
C5 C 0.0005(2) 0.1207(3) 0.57886(10) 0.0230(7) Uani 1 1 d . . . . .
H5 H -0.0567 0.1114 0.5605 0.028 Uiso 1 1 calc R U . . .
N2A N 0.24189(17) -0.33660(19) 0.58379(8) 0.0159(5) Uani 1 1 d . . . . .
C8 C 0.2729(2) 0.2109(2) 0.49266(9) 0.0172(6) Uani 1 1 d . . . . .
H8 H 0.2806 0.2835 0.5066 0.021 Uiso 1 1 calc R U . . .
C29 C 0.4958(2) 0.1469(3) 0.53451(9) 0.0229(7) Uani 1 1 d . . . . .
H29A H 0.4863 0.2221 0.5207 0.034 Uiso 1 1 calc R U . . .
H29B H 0.4529 0.0938 0.5177 0.034 Uiso 1 1 calc R U . . .
H29C H 0.5584 0.1223 0.5316 0.034 Uiso 1 1 calc R U . . .
C7 C 0.25410(19) 0.1183(2) 0.52006(9) 0.0148(6) Uani 1 1 d . . . . .
C26A C 0.0506(2) -0.3476(3) 0.73268(10) 0.0280(8) Uani 1 1 d . . . . .
H26A H 0.1036 -0.3904 0.7467 0.042 Uiso 1 1 calc R U . . .
H26B H -0.0052 -0.3803 0.7428 0.042 Uiso 1 1 calc R U . . .
H26C H 0.0561 -0.2690 0.7432 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2446(2) 0.0117(2) 0.50076(10) 0.0216(7) Uani 1 1 d . . . . .
H12 H 0.2322 -0.0509 0.5200 0.026 Uiso 1 1 calc R U . . .
C1A C 0.3510(2) -0.3499(2) 0.64904(10) 0.0169(6) Uani 1 1 d . . . . .
C24 C 0.45447(19) 0.0550(2) 0.61363(9) 0.0172(6) Uani 1 1 d . . . . .
C11A C 0.3126(2) -0.4750(3) 0.79304(11) 0.0298(8) Uani 1 1 d . . . . .
H11A H 0.3283 -0.5453 0.8077 0.036 Uiso 1 1 calc R U . . .
C40A C 0.2155(2) 0.0566(3) 0.79475(11) 0.0316(8) Uani 1 1 d . . . . .
C26 C 0.4341(2) 0.0186(3) 0.70278(10) 0.0259(7) Uani 1 1 d . . . . .
H26D H 0.3879 -0.0374 0.6917 0.039 Uiso 1 1 calc R U . . .
H26E H 0.4114 0.0651 0.7275 0.039 Uiso 1 1 calc R U . . .
H26F H 0.4901 -0.0199 0.7157 0.039 Uiso 1 1 calc R U . . .
C12A C 0.3094(2) -0.4635(3) 0.74390(10) 0.0244(7) Uani 1 1 d . . . . .
H12A H 0.3228 -0.5258 0.7248 0.029 Uiso 1 1 calc R U . . .
C3A C 0.5105(2) -0.3534(2) 0.63872(11) 0.0239(7) Uani 1 1 d . . . . .
H3A H 0.5727 -0.3550 0.6515 0.029 Uiso 1 1 calc R U . . .
C2A C 0.4450(2) -0.3547(2) 0.66828(10) 0.0219(7) Uani 1 1 d . . . . .
H2A H 0.4608 -0.3587 0.7016 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2536(2) -0.0028(3) 0.45281(10) 0.0274(8) Uani 1 1 d . . . . .
H11 H 0.2481 -0.0758 0.4391 0.033 Uiso 1 1 calc R U . . .
C25 C 0.4397(2) -0.0625(2) 0.59587(11) 0.0246(7) Uani 1 1 d . . . . .
H25A H 0.3991 -0.1021 0.6155 0.037 Uiso 1 1 calc R U . . .
H25B H 0.4984 -0.1018 0.5975 0.037 Uiso 1 1 calc R U . . .
H25C H 0.4120 -0.0607 0.5629 0.037 Uiso 1 1 calc R U . . .
C40 C 0.2379(2) -0.0198(3) 0.94641(11) 0.0270(8) Uani 1 1 d . . . . .
C25A C 0.0951(2) -0.5635(2) 0.67428(11) 0.0274(7) Uani 1 1 d . . . . .
H25D H 0.0407 -0.6099 0.6766 0.041 Uiso 1 1 calc R U . . .
H25E H 0.1270 -0.5520 0.7060 0.041 Uiso 1 1 calc R U . . .
H25F H 0.1358 -0.6017 0.6542 0.041 Uiso 1 1 calc R U . . .
C28A C 0.01677(19) -0.3119(3) 0.59886(10) 0.0206(7) Uani 1 1 d . . . . .
C6A C 0.3292(2) -0.3433(2) 0.59750(9) 0.0159(6) Uani 1 1 d . . . . .
C5A C 0.4016(2) -0.3444(2) 0.56753(10) 0.0207(7) Uani 1 1 d . . . . .
H5A H 0.3887 -0.3414 0.5340 0.025 Uiso 1 1 calc R U . . .
C29A C -0.0155(2) -0.2507(3) 0.55398(11) 0.0300(8) Uani 1 1 d . . . . .
H29D H 0.0117 -0.2850 0.5274 0.045 Uiso 1 1 calc R U . . .
H29E H 0.0028 -0.1714 0.5569 0.045 Uiso 1 1 calc R U . . .
H29F H -0.0821 -0.2557 0.5483 0.045 Uiso 1 1 calc R U . . .
HN2A H 0.2234(19) -0.326(2) 0.5525(10) 0.015(7) Uiso 1 1 d . . . . .
HN2 H 0.250(2) 0.183(3) 0.6883(11) 0.029(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1A N2A 2.015(2) . ?
Ir1A N1A 2.057(2) . ?
Ir1A C28A 2.166(3) . ?
Ir1A C23A 2.167(3) . ?
Ir1A C22A 2.169(3) . ?
Ir1A C21A 2.215(3) . ?
Ir1A C20A 2.228(3) . ?
Ir1A Cl1A 2.3843(11) . ?
Ir1 N1 2.014(2) . ?
Ir1 N2 2.061(2) . ?
Ir1 C20 2.158(3) . ?
Ir1 C21 2.166(3) . ?
Ir1 C24 2.174(3) . ?
Ir1 C23 2.218(3) . ?
Ir1 C22 2.233(3) . ?
Ir1 Cl1 2.3827(11) . ?
S1A O3A 1.436(2) . ?
S1A O1A 1.441(2) . ?
S1A O2A 1.451(2) . ?
S1A C40A 1.828(4) . ?
S1 O2 1.411(2) . ?
S1 O3 1.437(3) . ?
S1 O1 1.448(2) . ?
S1 C40 1.827(3) . ?
C20 C24 1.442(4) . ?
C20 C21 1.445(4) . ?
C20 C26 1.503(4) . ?
C23A C22A 1.431(4) . ?
C23A C28A 1.446(4) . ?
C23A C24A 1.493(4) . ?
F2A C40A 1.337(4) . ?
C28 C22 1.490(4) . ?
F3 C40 1.335(3) . ?
C9 C10 1.384(4) . ?
C9 C8 1.388(4) . ?
C27A C20A 1.497(4) . ?
F2 C40 1.326(4) . ?
C7A C12A 1.386(4) . ?
C7A C8A 1.397(4) . ?
C7A N1A 1.442(3) . ?
C2 N1 1.310(4) . ?
C2 C3 1.427(4) . ?
C2 C1 1.471(4) . ?
F1 C40 1.333(4) . ?
F3A C40A 1.346(4) . ?
C8A C9A 1.388(4) . ?
C4A C5A 1.347(4) . ?
C4A C3A 1.448(4) . ?
F1A C40A 1.329(4) . ?
C1 N2 1.323(4) . ?
C1 C6 1.433(4) . ?
C10 C11 1.386(4) . ?
N2 C7 1.440(3) . ?
C22 C23 1.428(4) . ?
C22 C21 1.449(4) . ?
C3 C4 1.344(4) . ?
C22A C21A 1.456(4) . ?
C22A C25A 1.499(4) . ?
N1A C1A 1.321(4) . ?
C6 C5 1.347(4) . ?
C20A C21A 1.431(4) . ?
C20A C28A 1.446(4) . ?
C23 C24 1.455(4) . ?
C23 C29 1.495(4) . ?
C9A C10A 1.384(5) . ?
C27 C21 1.501(4) . ?
C21A C26A 1.495(4) . ?
C4 C5 1.446(4) . ?
C10A C11A 1.383(5) . ?
N2A C6A 1.307(4) . ?
C8 C7 1.391(4) . ?
C7 C12 1.380(4) . ?
C12 C11 1.391(4) . ?
C1A C2A 1.436(4) . ?
C1A C6A 1.465(4) . ?
C24 C25 1.492(4) . ?
C11A C12A 1.396(4) . ?
C3A C2A 1.344(4) . ?
C28A C29A 1.499(4) . ?
C6A C5A 1.434(4) . ?

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
N2A Ir1A N1A 76.33(10) . . ?
N2A Ir1A C28A 108.92(11) . . ?
N1A Ir1A C28A 169.00(10) . . ?
N2A Ir1A C23A 98.46(11) . . ?
N1A Ir1A C23A 131.85(10) . . ?
C28A Ir1A C23A 39.00(11) . . ?
N2A Ir1A C22A 122.07(10) . . ?
N1A Ir1A C22A 104.11(10) . . ?
C28A Ir1A C22A 64.89(11) . . ?
C23A Ir1A C22A 38.56(10) . . ?
N2A Ir1A C21A 160.76(10) . . ?
N1A Ir1A C21A 107.25(10) . . ?
C28A Ir1A C21A 64.56(11) . . ?
C23A Ir1A C21A 64.73(11) . . ?
C22A Ir1A C21A 38.79(10) . . ?
N2A Ir1A C20A 144.95(11) . . ?
N1A Ir1A C20A 138.33(10) . . ?
C28A Ir1A C20A 38.38(11) . . ?
C23A Ir1A C20A 64.11(11) . . ?
C22A Ir1A C20A 63.72(11) . . ?
C21A Ir1A C20A 37.58(10) . . ?
N2A Ir1A Cl1A 85.97(7) . . ?
N1A Ir1A Cl1A 86.54(7) . . ?
C28A Ir1A Cl1A 103.28(8) . . ?
C23A Ir1A Cl1A 141.43(8) . . ?
C22A Ir1A Cl1A 151.46(8) . . ?
C21A Ir1A Cl1A 112.91(8) . . ?
C20A Ir1A Cl1A 90.59(8) . . ?
N1 Ir1 N2 76.12(10) . . ?
N1 Ir1 C20 98.82(10) . . ?
N2 Ir1 C20 132.49(10) . . ?
N1 Ir1 C21 109.30(11) . . ?
N2 Ir1 C21 169.52(10) . . ?
C20 Ir1 C21 39.05(11) . . ?
N1 Ir1 C24 122.37(10) . . ?
N2 Ir1 C24 104.28(10) . . ?
C20 Ir1 C24 38.88(10) . . ?
C21 Ir1 C24 65.25(11) . . ?
N1 Ir1 C23 160.96(10) . . ?
N2 Ir1 C23 107.37(10) . . ?
C20 Ir1 C23 64.67(11) . . ?
C21 Ir1 C23 64.53(11) . . ?
C24 Ir1 C23 38.68(10) . . ?
N1 Ir1 C22 145.38(10) . . ?
N2 Ir1 C22 138.03(10) . . ?
C20 Ir1 C22 64.06(11) . . ?
C21 Ir1 C22 38.42(10) . . ?
C24 Ir1 C22 63.75(11) . . ?
C23 Ir1 C22 37.42(10) . . ?
N1 Ir1 Cl1 85.87(7) . . ?
N2 Ir1 Cl1 87.44(7) . . ?
C20 Ir1 Cl1 139.88(8) . . ?
C21 Ir1 Cl1 101.72(8) . . ?
C24 Ir1 Cl1 151.07(8) . . ?
C23 Ir1 Cl1 112.76(7) . . ?
C22 Ir1 Cl1 89.74(8) . . ?
O3A S1A O1A 116.55(13) . . ?
O3A S1A O2A 114.26(14) . . ?
O1A S1A O2A 114.01(13) . . ?
O3A S1A C40A 103.93(14) . . ?
O1A S1A C40A 103.46(15) . . ?
O2A S1A C40A 102.19(14) . . ?
O2 S1 O3 115.91(16) . . ?
O2 S1 O1 115.46(15) . . ?
O3 S1 O1 113.71(15) . . ?
O2 S1 C40 103.97(15) . . ?
O3 S1 C40 102.83(15) . . ?
O1 S1 C40 102.44(14) . . ?
C24 C20 C21 108.3(2) . . ?
C24 C20 C26 125.0(3) . . ?
C21 C20 C26 126.7(2) . . ?
C24 C20 Ir1 71.16(16) . . ?
C21 C20 Ir1 70.78(16) . . ?
C26 C20 Ir1 124.5(2) . . ?
C22A C23A C28A 107.8(2) . . ?
C22A C23A C24A 125.2(3) . . ?
C28A C23A C24A 127.0(3) . . ?
C22A C23A Ir1A 70.80(16) . . ?
C28A C23A Ir1A 70.49(16) . . ?
C24A C23A Ir1A 124.5(2) . . ?
C10 C9 C8 120.0(3) . . ?
C12A C7A C8A 121.3(3) . . ?
C12A C7A N1A 120.0(3) . . ?
C8A C7A N1A 118.7(3) . . ?
N1 C2 C3 127.0(2) . . ?
N1 C2 C1 113.4(2) . . ?
C3 C2 C1 119.6(3) . . ?
C9A C8A C7A 118.8(3) . . ?
C5A C4A C3A 122.0(3) . . ?
N2 C1 C6 128.0(2) . . ?
N2 C1 C2 113.2(2) . . ?
C6 C1 C2 118.8(3) . . ?
C9 C10 C11 120.4(3) . . ?
C1 N2 C7 119.2(2) . . ?
C1 N2 Ir1 117.14(17) . . ?
C7 N2 Ir1 123.31(18) . . ?
C23 C22 C21 108.9(2) . . ?
C23 C22 C28 126.2(3) . . ?
C21 C22 C28 124.8(3) . . ?
C23 C22 Ir1 70.74(16) . . ?
C21 C22 Ir1 68.30(16) . . ?
C28 C22 Ir1 126.6(2) . . ?
C4 C3 C2 119.0(3) . . ?
C23A C22A C21A 108.6(3) . . ?
C23A C22A C25A 126.4(3) . . ?
C21A C22A C25A 124.7(3) . . ?
C23A C22A Ir1A 70.64(16) . . ?
C21A C22A Ir1A 72.31(16) . . ?
C25A C22A Ir1A 127.8(2) . . ?
C1A N1A C7A 120.9(2) . . ?
C1A N1A Ir1A 116.85(18) . . ?
C7A N1A Ir1A 122.10(19) . . ?
C2 N1 Ir1 119.19(18) . . ?
C5 C6 C1 119.0(3) . . ?
C21A C20A C28A 108.9(3) . . ?
C21A C20A C27A 126.2(3) . . ?
C28A C20A C27A 125.0(3) . . ?
C21A C20A Ir1A 70.72(17) . . ?
C28A C20A Ir1A 68.51(16) . . ?
C27A C20A Ir1A 126.4(2) . . ?
C22 C23 C24 107.6(2) . . ?
C22 C23 C29 126.5(3) . . ?
C24 C23 C29 125.6(3) . . ?
C22 C23 Ir1 71.84(16) . . ?
C24 C23 Ir1 69.01(15) . . ?
C29 C23 Ir1 128.9(2) . . ?
C10A C9A C8A 120.1(3) . . ?
C20A C21A C22A 107.0(2) . . ?
C20A C21A C26A 128.1(3) . . ?
C22A C21A C26A 124.5(3) . . ?
C20A C21A Ir1A 71.70(17) . . ?
C22A C21A Ir1A 68.90(15) . . ?
C26A C21A Ir1A 129.4(2) . . ?
C3 C4 C5 121.8(3) . . ?
C11A C10A C9A 121.0(3) . . ?
C20 C21 C22 107.2(2) . . ?
C20 C21 C27 128.0(3) . . ?
C22 C21 C27 124.6(3) . . ?
C20 C21 Ir1 70.17(16) . . ?
C22 C21 Ir1 73.28(16) . . ?
C27 C21 Ir1 126.4(2) . . ?
C6 C5 C4 121.8(3) . . ?
C6A N2A Ir1A 118.59(19) . . ?
C9 C8 C7 119.0(3) . . ?
C12 C7 C8 121.4(2) . . ?
C12 C7 N2 120.6(2) . . ?
C8 C7 N2 118.0(2) . . ?
C7 C12 C11 119.0(3) . . ?
N1A C1A C2A 127.9(3) . . ?
N1A C1A C6A 113.3(3) . . ?
C2A C1A C6A 118.8(3) . . ?
C20 C24 C23 107.8(2) . . ?
C20 C24 C25 126.4(3) . . ?
C23 C24 C25 125.6(2) . . ?
C20 C24 Ir1 69.96(16) . . ?
C23 C24 Ir1 72.31(16) . . ?
C25 C24 Ir1 127.6(2) . . ?
C10A C11A C12A 119.6(3) . . ?
F1A C40A F2A 108.3(3) . . ?
F1A C40A F3A 107.4(3) . . ?
F2A C40A F3A 107.4(3) . . ?
F1A C40A S1A 111.9(2) . . ?
F2A C40A S1A 111.4(2) . . ?
F3A C40A S1A 110.3(2) . . ?
C7A C12A C11A 119.3(3) . . ?
C2A C3A C4A 121.4(3) . . ?
C3A C2A C1A 119.4(3) . . ?
C10 C11 C12 120.1(3) . . ?
F2 C40 F1 107.7(3) . . ?
F2 C40 F3 106.6(3) . . ?
F1 C40 F3 107.4(3) . . ?
F2 C40 S1 112.5(2) . . ?
F1 C40 S1 109.9(2) . . ?
F3 C40 S1 112.4(2) . . ?
C20A C28A C23A 107.5(2) . . ?
C20A C28A C29A 125.1(3) . . ?
C23A C28A C29A 127.1(3) . . ?
C20A C28A Ir1A 73.11(17) . . ?
C23A C28A Ir1A 70.51(16) . . ?
C29A C28A Ir1A 126.5(2) . . ?
N2A C6A C5A 126.6(3) . . ?
N2A C6A C1A 113.9(2) . . ?
C5A C6A C1A 119.5(3) . . ?
C4A C5A C6A 118.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12A C7A C8A C9A 0.1(5) . . . . ?
N1A C7A C8A C9A 177.0(3) . . . . ?
N1 C2 C1 N2 -0.6(3) . . . . ?
C3 C2 C1 N2 177.9(2) . . . . ?
N1 C2 C1 C6 -178.5(2) . . . . ?
C3 C2 C1 C6 -0.1(4) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C6 C1 N2 C7 -2.6(4) . . . . ?
C2 C1 N2 C7 179.6(2) . . . . ?
C6 C1 N2 Ir1 171.1(2) . . . . ?
C2 C1 N2 Ir1 -6.7(3) . . . . ?
N1 C2 C3 C4 176.8(3) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C28A C23A C22A C21A 1.6(3) . . . . ?
C24A C23A C22A C21A -178.1(3) . . . . ?
Ir1A C23A C22A C21A 62.7(2) . . . . ?
C28A C23A C22A C25A 175.7(3) . . . . ?
C24A C23A C22A C25A -4.0(5) . . . . ?
Ir1A C23A C22A C25A -123.2(3) . . . . ?
C28A C23A C22A Ir1A -61.1(2) . . . . ?
C24A C23A C22A Ir1A 119.2(3) . . . . ?
C12A C7A N1A C1A -71.6(4) . . . . ?
C8A C7A N1A C1A 111.4(3) . . . . ?
C12A C7A N1A Ir1A 113.0(3) . . . . ?
C8A C7A N1A Ir1A -63.9(3) . . . . ?
C3 C2 N1 Ir1 -170.4(2) . . . . ?
C1 C2 N1 Ir1 7.8(3) . . . . ?
N2 C1 C6 C5 -176.0(3) . . . . ?
C2 C1 C6 C5 1.6(4) . . . . ?
C21 C22 C23 C24 -2.3(3) . . . . ?
C28 C22 C23 C24 178.2(3) . . . . ?
Ir1 C22 C23 C24 -60.01(19) . . . . ?
C21 C22 C23 C29 -176.9(3) . . . . ?
C28 C22 C23 C29 3.6(5) . . . . ?
Ir1 C22 C23 C29 125.4(3) . . . . ?
C21 C22 C23 Ir1 57.7(2) . . . . ?
C28 C22 C23 Ir1 -121.8(3) . . . . ?
C7A C8A C9A C10A -0.3(5) . . . . ?
C28A C20A C21A C22A -2.1(3) . . . . ?
C27A C20A C21A C22A 178.4(3) . . . . ?
Ir1A C20A C21A C22A -60.1(2) . . . . ?
C28A C20A C21A C26A -175.8(3) . . . . ?
C27A C20A C21A C26A 4.7(5) . . . . ?
Ir1A C20A C21A C26A 126.2(3) . . . . ?
C28A C20A C21A Ir1A 58.0(2) . . . . ?
C27A C20A C21A Ir1A -121.5(3) . . . . ?
C23A C22A C21A C20A 0.3(3) . . . . ?
C25A C22A C21A C20A -173.9(3) . . . . ?
Ir1A C22A C21A C20A 62.0(2) . . . . ?
C23A C22A C21A C26A 174.3(3) . . . . ?
C25A C22A C21A C26A 0.1(5) . . . . ?
Ir1A C22A C21A C26A -124.1(3) . . . . ?
C23A C22A C21A Ir1A -61.7(2) . . . . ?
C25A C22A C21A Ir1A 124.1(3) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C8A C9A C10A C11A 0.3(5) . . . . ?
C24 C20 C21 C22 -2.8(3) . . . . ?
C26 C20 C21 C22 176.4(3) . . . . ?
Ir1 C20 C21 C22 -64.4(2) . . . . ?
C24 C20 C21 C27 -177.1(3) . . . . ?
C26 C20 C21 C27 2.1(5) . . . . ?
Ir1 C20 C21 C27 121.2(3) . . . . ?
C24 C20 C21 Ir1 61.6(2) . . . . ?
C26 C20 C21 Ir1 -119.2(3) . . . . ?
C23 C22 C21 C20 3.1(3) . . . . ?
C28 C22 C21 C20 -177.3(3) . . . . ?
Ir1 C22 C21 C20 62.36(19) . . . . ?
C23 C22 C21 C27 177.7(3) . . . . ?
C28 C22 C21 C27 -2.7(5) . . . . ?
Ir1 C22 C21 C27 -123.1(3) . . . . ?
C23 C22 C21 Ir1 -59.2(2) . . . . ?
C28 C22 C21 Ir1 120.4(3) . . . . ?
C1 C6 C5 C4 -1.6(4) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C10 C9 C8 C7 -1.2(4) . . . . ?
C9 C8 C7 C12 1.5(4) . . . . ?
C9 C8 C7 N2 -179.0(3) . . . . ?
C1 N2 C7 C12 -73.6(4) . . . . ?
Ir1 N2 C7 C12 113.1(3) . . . . ?
C1 N2 C7 C8 106.9(3) . . . . ?
Ir1 N2 C7 C8 -66.4(3) . . . . ?
C8 C7 C12 C11 -0.4(5) . . . . ?
N2 C7 C12 C11 -179.9(3) . . . . ?
C7A N1A C1A C2A -4.8(4) . . . . ?
Ir1A N1A C1A C2A 170.8(2) . . . . ?
C7A N1A C1A C6A 176.7(2) . . . . ?
Ir1A N1A C1A C6A -7.8(3) . . . . ?
C21 C20 C24 C23 1.4(3) . . . . ?
C26 C20 C24 C23 -177.8(3) . . . . ?
Ir1 C20 C24 C23 62.8(2) . . . . ?
C21 C20 C24 C25 176.1(3) . . . . ?
C26 C20 C24 C25 -3.1(5) . . . . ?
Ir1 C20 C24 C25 -122.5(3) . . . . ?
C21 C20 C24 Ir1 -61.4(2) . . . . ?
C26 C20 C24 Ir1 119.4(3) . . . . ?
C22 C23 C24 C20 0.5(3) . . . . ?
C29 C23 C24 C20 175.2(3) . . . . ?
Ir1 C23 C24 C20 -61.28(19) . . . . ?
C22 C23 C24 C25 -174.2(3) . . . . ?
C29 C23 C24 C25 0.4(5) . . . . ?
Ir1 C23 C24 C25 124.0(3) . . . . ?
C22 C23 C24 Ir1 61.8(2) . . . . ?
C29 C23 C24 Ir1 -123.5(3) . . . . ?
C9A C10A C11A C12A -0.2(5) . . . . ?
O3A S1A C40A F1A 59.8(3) . . . . ?
O1A S1A C40A F1A -62.4(2) . . . . ?
O2A S1A C40A F1A 178.9(2) . . . . ?
O3A S1A C40A F2A -61.6(2) . . . . ?
O1A S1A C40A F2A 176.2(2) . . . . ?
O2A S1A C40A F2A 57.6(2) . . . . ?
O3A S1A C40A F3A 179.3(2) . . . . ?
O1A S1A C40A F3A 57.1(3) . . . . ?
O2A S1A C40A F3A -61.6(3) . . . . ?
C8A C7A C12A C11A 0.0(5) . . . . ?
N1A C7A C12A C11A -176.8(3) . . . . ?
C10A C11A C12A C7A 0.0(5) . . . . ?
C5A C4A C3A C2A 1.7(4) . . . . ?
C4A C3A C2A C1A -1.3(4) . . . . ?
N1A C1A C2A C3A -178.7(3) . . . . ?
C6A C1A C2A C3A -0.3(4) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C7 C12 C11 C10 -0.9(5) . . . . ?
O2 S1 C40 F2 58.3(3) . . . . ?
O3 S1 C40 F2 179.6(2) . . . . ?
O1 S1 C40 F2 -62.2(2) . . . . ?
O2 S1 C40 F1 178.3(2) . . . . ?
O3 S1 C40 F1 -60.4(3) . . . . ?
O1 S1 C40 F1 57.8(2) . . . . ?
O2 S1 C40 F3 -62.1(3) . . . . ?
O3 S1 C40 F3 59.2(3) . . . . ?
O1 S1 C40 F3 177.4(2) . . . . ?
C21A C20A C28A C23A 3.2(3) . . . . ?
C27A C20A C28A C23A -177.4(3) . . . . ?
Ir1A C20A C28A C23A 62.51(19) . . . . ?
C21A C20A C28A C29A 177.5(3) . . . . ?
C27A C20A C28A C29A -3.0(5) . . . . ?
Ir1A C20A C28A C29A -123.2(3) . . . . ?
C21A C20A C28A Ir1A -59.4(2) . . . . ?
C27A C20A C28A Ir1A 120.1(3) . . . . ?
C22A C23A C28A C20A -2.9(3) . . . . ?
C24A C23A C28A C20A 176.8(3) . . . . ?
Ir1A C23A C28A C20A -64.2(2) . . . . ?
C22A C23A C28A C29A -177.1(3) . . . . ?
C24A C23A C28A C29A 2.6(5) . . . . ?
Ir1A C23A C28A C29A 121.6(3) . . . . ?
C22A C23A C28A Ir1A 61.3(2) . . . . ?
C24A C23A C28A Ir1A -119.0(3) . . . . ?
Ir1A N2A C6A C5A -172.2(2) . . . . ?
Ir1A N2A C6A C1A 7.6(3) . . . . ?
N1A C1A C6A N2A 0.3(3) . . . . ?
C2A C1A C6A N2A -178.4(2) . . . . ?
N1A C1A C6A C5A -179.9(2) . . . . ?
C2A C1A C6A C5A 1.5(4) . . . . ?
C3A C4A C5A C6A -0.5(4) . . . . ?
N2A C6A C5A C4A 178.8(3) . . . . ?
C1A C6A C5A C4A -1.1(4) . . . . ?

_refine_diff_density_max         1.116
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.098

