# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_compound6
_database_code_depnum_ccdc_archive 'CCDC 1849635'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2018-08-28 downloaded from the CCDC.
;

_audit_creation_date             2017-04-26T14:43:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C23 H26 Ir1 N1 O3'
_chemical_formula_sum            'C23 H26 Ir N O3'
_chemical_formula_weight         556.65
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
_cell_length_a                   16.13031(15)
_cell_length_b                   14.54437(12)
_cell_length_c                   17.33703(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4067.35(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    20060
_cell_measurement_theta_min      4.789
_cell_measurement_theta_max      76.375
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.043
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2176
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0699
0 2 -3 0.0738
-5 -1 0 0.0232
5 1 0 0.0197
1 5 1 0.0396
0 1 5 0.0564
-1 -5 -1 0.0155
-1 -5 2 0.025


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    12.917
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.267
_exptl_absorpt_correction_T_max  0.648

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0149789
_diffrn_orient_matrix_ub_12      0.066876
_diffrn_orient_matrix_ub_13      -0.0675372
_diffrn_orient_matrix_ub_21      0.094303
_diffrn_orient_matrix_ub_22      0.0086692
_diffrn_orient_matrix_ub_23      -0.0121277
_diffrn_orient_matrix_ub_31      -0.0022692
_diffrn_orient_matrix_ub_32      -0.0816203
_diffrn_orient_matrix_ub_33      -0.0565145
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_number            33175
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.824
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             3856
_reflns_number_gt                3570
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  96.00   1.00    2.00    --   40.83-125.00-180.00   67
  2  ω     33.00  92.00   1.00    2.00    --   40.83  77.00  90.00   59
  3  ω      6.00  48.00   1.00    2.00    --   40.83-132.00  63.00   42
  4  ω    105.00 147.00   1.00    8.00    --  113.00  30.00  60.00   42
  5  ω     36.00  66.00   1.00    8.00    --  113.00 -30.00  30.00   30
  6  ω     38.00  63.00   1.00    8.00    --  113.00 -45.00 120.00   25
  7  ω    117.00 154.00   1.00    8.00    --  113.00 137.00 -49.00   37
  8  ω     47.00  73.00   1.00    8.00    --  113.00 -45.00   0.00   26
  9  ω    133.00 158.00   1.00    8.00    --  113.00  61.00-120.00   25
 10  ω     41.00  74.00   1.00    8.00    --  113.00 -45.00 -30.00   33
 11  ω     79.00 155.00   1.00    8.00    --  113.00  77.00 150.00   76
 12  ω     35.00  65.00   1.00    8.00    --  113.00 -30.00  60.00   30
 13  ω     35.00  65.00   1.00    8.00    --  113.00 -30.00  90.00   30
 14  ω   -111.00 -12.00   1.00    2.00    --  -40.83 -77.00-120.00   99
 15  ω     79.00 117.00   1.00    2.00    --   40.83  37.00 120.00   38
 16  ω    -33.00  74.00   1.00    2.00    --   40.83 -77.00 -30.00  107
 17  ω     27.00  54.00   1.00    2.00    --   40.83  37.00 120.00   27
 18  ω    -68.00 -40.00   1.00    8.00    --  -83.00  30.00 150.00   28
 19  ω    -57.00  -5.00   1.00    8.00    --  -83.00  30.00-120.00   52
 20  ω     63.00 109.00   1.00    8.00    --  113.00 -94.00   0.00   46
 21  ω     35.00  69.00   1.00    8.00    --  113.00 -30.00-120.00   34
 22  ω     55.00 112.00   1.00    8.00    --  113.00-111.00 -90.00   57
 23  ω     33.00  96.00   1.00    8.00    --  113.00 -15.00-120.00   63
 24  ω     35.00  69.00   1.00    8.00    --  113.00 -30.00-180.00   34
 25  ω     87.00 114.00   1.00    8.00    --  113.00  30.00 150.00   27
 26  ω     35.00  68.00   1.00    8.00    --  113.00 -30.00-150.00   33
 27  ω     56.00  83.00   1.00    8.00    --  113.00 -94.00  60.00   27
 28  ω     43.00 102.00   1.00    8.00    --  113.00 -94.00 150.00   59
 29  ω     86.00 112.00   1.00    8.00    --  113.00-111.00 -30.00   26
 30  ω     59.00 108.00   1.00    8.00    --  113.00-111.00-120.00   49
 31  ω     35.00  69.00   1.00    8.00    --  113.00 -30.00 150.00   34
 32  ω     53.00 116.00   1.00    8.00    --  113.00-111.00 120.00   63
 33  ω    111.00 149.00   1.00    8.00    --  113.00 -15.00-120.00   38
 34  ω     49.00 137.00   1.00    8.00    --  113.00 -61.00-120.00   88
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+3.2166P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3856
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0191
_refine_ls_R_factor_gt           0.0172
_refine_ls_wR_factor_ref         0.045
_refine_ls_wR_factor_gt          0.0437
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.64
_refine_diff_density_rms         0.08

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_number_in_cell
C 184
H 208
Ir 8
N 8
O 24

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.17921(2) 0.18386(2) 0.55442(2) 0.01310(5) Uani 1 d . .
O1 O 0.20490(11) 0.15458(12) 0.74023(9) 0.0230(3) Uani 1 d . .
O2 O 0.10940(11) 0.06050(11) 0.56009(9) 0.0190(3) Uani 1 d . .
O3 O 0.07498(11) 0.07865(12) 0.68478(10) 0.0245(4) Uani 1 d . .
N1 N 0.26946(11) 0.11978(12) 0.62499(11) 0.0152(4) Uani 1 d . .
C1 C 0.27160(14) 0.12517(15) 0.70256(13) 0.0182(4) Uani 1 d . .
C2 C 0.34253(16) 0.10142(17) 0.74456(14) 0.0232(5) Uani 1 d . .
H2 H 0.344247 0.109609 0.798902 0.028 Uiso 1 calc . .
C3 C 0.40986(15) 0.06594(17) 0.70570(14) 0.0238(5) Uani 1 d . .
H3 H 0.459294 0.051014 0.732719 0.029 Uiso 1 calc . .
C4 C 0.40458(14) 0.05225(16) 0.62659(13) 0.0207(5) Uani 1 d . .
H4 H 0.449053 0.023728 0.599787 0.025 Uiso 1 calc . .
C5 C 0.33485(14) 0.08002(15) 0.58686(14) 0.0167(4) Uani 1 d . .
C6 C 0.32224(13) 0.07281(15) 0.50355(13) 0.0153(4) Uani 1 d . .
C7 C 0.37747(15) 0.02659(16) 0.45441(14) 0.0201(5) Uani 1 d . .
H7 H 0.42581 -0.001477 0.475034 0.024 Uiso 1 calc . .
C8 C 0.36176(15) 0.02178(16) 0.37613(14) 0.0228(5) Uani 1 d . .
H8 H 0.39961 -0.008165 0.342496 0.027 Uiso 1 calc . .
C9 C 0.28972(17) 0.06143(16) 0.34742(13) 0.0237(5) Uani 1 d . .
H9 H 0.278113 0.057597 0.2938 0.028 Uiso 1 calc . .
C10 C 0.23434(15) 0.10661(15) 0.39575(13) 0.0205(5) Uani 1 d . .
H10 H 0.185146 0.132379 0.37476 0.025 Uiso 1 calc . .
C11 C 0.24998(14) 0.11471(14) 0.47504(13) 0.0162(4) Uani 1 d . .
C12 C 0.20015(16) 0.31860(14) 0.50793(14) 0.0170(4) Uani 1 d . .
C13 C 0.11858(14) 0.28712(15) 0.48467(13) 0.0172(4) Uani 1 d . .
C14 C 0.07033(15) 0.27691(16) 0.55414(14) 0.0209(5) Uani 1 d . .
C15 C 0.11860(16) 0.30178(15) 0.61903(15) 0.0217(5) Uani 1 d . .
C16 C 0.20055(17) 0.32464(14) 0.59036(15) 0.0197(5) Uani 1 d . .
C17 C 0.26962(15) 0.34529(17) 0.45534(14) 0.0224(5) Uani 1 d . .
H17A H 0.322497 0.339157 0.482694 0.034 Uiso 1 calc . .
H17B H 0.262245 0.40921 0.438828 0.034 Uiso 1 calc . .
H17C H 0.269625 0.304989 0.410037 0.034 Uiso 1 calc . .
C18 C 0.08581(16) 0.28105(16) 0.40424(15) 0.0250(5) Uani 1 d . .
H18A H 0.131827 0.285915 0.367559 0.038 Uiso 1 calc . .
H18B H 0.046485 0.331288 0.395254 0.038 Uiso 1 calc . .
H18C H 0.057606 0.221973 0.397133 0.038 Uiso 1 calc . .
C19 C -0.01769(16) 0.24501(19) 0.55634(17) 0.0308(6) Uani 1 d . .
H19A H -0.028808 0.205998 0.511427 0.046 Uiso 1 calc . .
H19B H -0.054757 0.298391 0.555357 0.046 Uiso 1 calc . .
H19C H -0.027249 0.209737 0.60367 0.046 Uiso 1 calc . .
C20 C 0.0873(2) 0.31155(18) 0.69994(17) 0.0339(7) Uani 1 d . .
H20A H 0.05537 0.256756 0.71402 0.051 Uiso 1 calc . .
H20B H 0.051739 0.365999 0.703522 0.051 Uiso 1 calc . .
H20C H 0.134391 0.318295 0.735233 0.051 Uiso 1 calc . .
C21 C 0.27234(18) 0.35529(17) 0.63853(16) 0.0291(6) Uani 1 d . .
H21A H 0.268534 0.327166 0.689772 0.044 Uiso 1 calc . .
H21B H 0.271278 0.42239 0.643595 0.044 Uiso 1 calc . .
H21C H 0.324237 0.336401 0.613781 0.044 Uiso 1 calc . .
C22 C 0.06902(15) 0.03943(16) 0.62038(14) 0.0210(5) Uani 1 d . .
C23 C 0.00868(18) -0.03917(19) 0.61170(17) 0.0322(6) Uani 1 d . .
H23A H -0.047587 -0.014757 0.605761 0.048 Uiso 1 calc . .
H23B H 0.011126 -0.07833 0.657647 0.048 Uiso 1 calc . .
H23C H 0.023307 -0.075474 0.56607 0.048 Uiso 1 calc . .
H1 H 0.1592(13) 0.136(2) 0.7155(18) 0.039 Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O2 2.1206(16) . ?
Ir1 N1 2.1177(18) . ?
Ir1 C11 2.051(2) . ?
Ir1 C12 2.146(2) . ?
Ir1 C13 2.162(2) . ?
Ir1 C14 2.217(2) . ?
Ir1 C15 2.270(2) . ?
Ir1 C16 2.168(2) . ?
O1 C1 1.329(3) . ?
O1 H1 0.894(10) . ?
O2 C22 1.269(3) . ?
O3 C22 1.258(3) . ?
N1 C1 1.348(3) . ?
N1 C5 1.373(3) . ?
C1 C2 1.400(3) . ?
C2 H2 0.95 . ?
C2 C3 1.378(4) . ?
C3 H3 0.95 . ?
C3 C4 1.388(3) . ?
C4 H4 0.95 . ?
C4 C5 1.379(3) . ?
C5 C6 1.462(3) . ?
C6 C7 1.404(3) . ?
C6 C11 1.405(3) . ?
C7 H7 0.95 . ?
C7 C8 1.382(3) . ?
C8 H8 0.95 . ?
C8 C9 1.389(4) . ?
C9 H9 0.95 . ?
C9 C10 1.390(3) . ?
C10 H10 0.95 . ?
C10 C11 1.403(3) . ?
C12 C13 1.450(3) . ?
C12 C16 1.432(4) . ?
C12 C17 1.496(3) . ?
C13 C14 1.442(3) . ?
C13 C18 1.494(3) . ?
C14 C15 1.415(4) . ?
C14 C19 1.494(3) . ?
C15 C16 1.451(4) . ?
C15 C20 1.498(4) . ?
C16 C21 1.496(4) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 C23 1.509(3) . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?

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
O2 Ir1 C12 150.90(8) . . ?
O2 Ir1 C13 111.93(8) . . ?
O2 Ir1 C14 95.50(8) . . ?
O2 Ir1 C15 112.81(8) . . ?
O2 Ir1 C16 150.48(8) . . ?
N1 Ir1 O2 88.04(7) . . ?
N1 Ir1 C12 120.71(8) . . ?
N1 Ir1 C13 160.02(8) . . ?
N1 Ir1 C14 144.53(8) . . ?
N1 Ir1 C15 110.09(8) . . ?
N1 Ir1 C16 98.08(8) . . ?
C11 Ir1 O2 84.94(7) . . ?
C11 Ir1 N1 77.84(8) . . ?
C11 Ir1 C12 96.21(9) . . ?
C11 Ir1 C13 102.53(9) . . ?
C11 Ir1 C14 137.60(9) . . ?
C11 Ir1 C15 160.25(9) . . ?
C11 Ir1 C16 124.58(9) . . ?
C12 Ir1 C13 39.35(9) . . ?
C12 Ir1 C14 64.30(9) . . ?
C12 Ir1 C15 64.09(9) . . ?
C12 Ir1 C16 38.77(10) . . ?
C13 Ir1 C14 38.41(9) . . ?
C13 Ir1 C15 63.66(9) . . ?
C13 Ir1 C16 64.94(9) . . ?
C14 Ir1 C15 36.74(9) . . ?
C16 Ir1 C14 63.25(10) . . ?
C16 Ir1 C15 38.08(9) . . ?
C1 O1 H1 110(2) . . ?
C22 O2 Ir1 120.99(15) . . ?
C1 N1 Ir1 124.65(15) . . ?
C1 N1 C5 119.0(2) . . ?
C5 N1 Ir1 115.81(15) . . ?
O1 C1 N1 119.2(2) . . ?
O1 C1 C2 119.0(2) . . ?
N1 C1 C2 121.7(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120 . . ?
N1 C5 C4 120.6(2) . . ?
N1 C5 C6 113.51(19) . . ?
C4 C5 C6 125.8(2) . . ?
C7 C6 C5 123.0(2) . . ?
C7 C6 C11 121.4(2) . . ?
C11 C6 C5 115.58(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 118.9(2) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C6 C11 Ir1 115.98(16) . . ?
C10 C11 Ir1 126.77(17) . . ?
C10 C11 C6 117.2(2) . . ?
C13 C12 Ir1 70.93(12) . . ?
C13 C12 C17 126.3(2) . . ?
C16 C12 Ir1 71.45(12) . . ?
C16 C12 C13 107.5(2) . . ?
C16 C12 C17 126.1(2) . . ?
C17 C12 Ir1 125.73(16) . . ?
C12 C13 Ir1 69.72(12) . . ?
C12 C13 C18 126.8(2) . . ?
C14 C13 Ir1 72.86(13) . . ?
C14 C13 C12 106.9(2) . . ?
C14 C13 C18 125.6(2) . . ?
C18 C13 Ir1 129.88(16) . . ?
C13 C14 Ir1 68.72(12) . . ?
C13 C14 C19 124.5(2) . . ?
C15 C14 Ir1 73.65(13) . . ?
C15 C14 C13 109.9(2) . . ?
C15 C14 C19 125.6(2) . . ?
C19 C14 Ir1 124.27(17) . . ?
C14 C15 Ir1 69.60(13) . . ?
C14 C15 C16 106.7(2) . . ?
C14 C15 C20 125.7(3) . . ?
C16 C15 Ir1 67.15(12) . . ?
C16 C15 C20 127.3(3) . . ?
C20 C15 Ir1 132.77(17) . . ?
C12 C16 Ir1 69.78(12) . . ?
C12 C16 C15 108.9(2) . . ?
C12 C16 C21 125.4(2) . . ?
C15 C16 Ir1 74.77(13) . . ?
C15 C16 C21 125.6(2) . . ?
C21 C16 Ir1 124.40(17) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 C23 115.6(2) . . ?
O3 C22 O2 125.6(2) . . ?
O3 C22 C23 118.8(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ir1 O2 C22 O3 -11.3(3) . . . . ?
Ir1 O2 C22 C23 168.10(17) . . . . ?
Ir1 N1 C1 O1 15.5(3) . . . . ?
Ir1 N1 C1 C2 -163.88(17) . . . . ?
Ir1 N1 C5 C4 167.42(17) . . . . ?
Ir1 N1 C5 C6 -11.7(2) . . . . ?
Ir1 C12 C13 C14 63.88(15) . . . . ?
Ir1 C12 C13 C18 -125.3(2) . . . . ?
Ir1 C12 C16 C15 -65.05(15) . . . . ?
Ir1 C12 C16 C21 118.5(2) . . . . ?
Ir1 C13 C14 C15 62.45(16) . . . . ?
Ir1 C13 C14 C19 -117.8(2) . . . . ?
Ir1 C14 C15 C16 57.03(15) . . . . ?
Ir1 C14 C15 C20 -128.7(2) . . . . ?
Ir1 C15 C16 C12 61.85(14) . . . . ?
Ir1 C15 C16 C21 -121.7(2) . . . . ?
O1 C1 C2 C3 176.3(2) . . . . ?
N1 C1 C2 C3 -4.3(4) . . . . ?
N1 C5 C6 C7 -173.7(2) . . . . ?
N1 C5 C6 C11 5.7(3) . . . . ?
C1 N1 C5 C4 -4.9(3) . . . . ?
C1 N1 C5 C6 176.02(19) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C2 C3 C4 C5 4.6(4) . . . . ?
C3 C4 C5 N1 -1.2(3) . . . . ?
C3 C4 C5 C6 177.8(2) . . . . ?
C4 C5 C6 C7 7.3(3) . . . . ?
C4 C5 C6 C11 -173.4(2) . . . . ?
C5 N1 C1 O1 -172.92(19) . . . . ?
C5 N1 C1 C2 7.7(3) . . . . ?
C5 C6 C7 C8 179.6(2) . . . . ?
C5 C6 C11 Ir1 3.2(2) . . . . ?
C5 C6 C11 C10 -177.94(19) . . . . ?
C6 C7 C8 C9 -1.5(4) . . . . ?
C7 C6 C11 Ir1 -177.44(17) . . . . ?
C7 C6 C11 C10 1.5(3) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C9 C10 C11 Ir1 176.74(17) . . . . ?
C9 C10 C11 C6 -2.0(3) . . . . ?
C11 C6 C7 C8 0.3(3) . . . . ?
C12 C13 C14 Ir1 -61.81(14) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C12 C13 C14 C19 -179.6(2) . . . . ?
C13 C12 C16 Ir1 62.15(14) . . . . ?
C13 C12 C16 C15 -2.9(2) . . . . ?
C13 C12 C16 C21 -179.4(2) . . . . ?
C13 C14 C15 Ir1 -59.43(15) . . . . ?
C13 C14 C15 C16 -2.4(3) . . . . ?
C13 C14 C15 C20 171.9(2) . . . . ?
C14 C15 C16 Ir1 -58.58(15) . . . . ?
C14 C15 C16 C12 3.3(2) . . . . ?
C14 C15 C16 C21 179.7(2) . . . . ?
C16 C12 C13 Ir1 -62.48(14) . . . . ?
C16 C12 C13 C14 1.4(2) . . . . ?
C16 C12 C13 C18 172.3(2) . . . . ?
C17 C12 C13 Ir1 120.8(2) . . . . ?
C17 C12 C13 C14 -175.3(2) . . . . ?
C17 C12 C13 C18 -4.4(4) . . . . ?
C17 C12 C16 Ir1 -121.2(2) . . . . ?
C17 C12 C16 C15 173.8(2) . . . . ?
C17 C12 C16 C21 -2.7(3) . . . . ?
C18 C13 C14 Ir1 127.2(2) . . . . ?
C18 C13 C14 C15 -170.4(2) . . . . ?
C18 C13 C14 C19 9.4(4) . . . . ?
C19 C14 C15 Ir1 120.8(2) . . . . ?
C19 C14 C15 C16 177.8(2) . . . . ?
C19 C14 C15 C20 -7.9(4) . . . . ?
C20 C15 C16 Ir1 127.3(2) . . . . ?
C20 C15 C16 C12 -170.9(2) . . . . ?
C20 C15 C16 C21 5.6(4) . . . . ?

