# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_73
_database_code_depnum_ccdc_archive 'CCDC 1974083'
loop_
_audit_author_name
_audit_author_address
'Jun Yoshida'
;Kitasato University
Japan
;
_audit_update_record             
;
2019-12-26 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_audit_creation_date             2019-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H32 Cl Ir N2'
_chemical_formula_sum            'C34 H32 Cl Ir N2'
_chemical_formula_weight         696.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C34 H32 Ir N2 Cl'
_chemical_oxdiff_usercomment     YG129
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4178(6)
_cell_length_b                   11.1107(8)
_cell_length_c                   14.0254(6)
_cell_angle_alpha                79.931(4)
_cell_angle_beta                 79.001(4)
_cell_angle_gamma                68.307(6)
_cell_volume                     1329.82(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7445
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.4010
_cell_measurement_theta_min      3.2530
_shelx_estimated_absorpt_T_max   0.562
_shelx_estimated_absorpt_T_min   0.281
_exptl_absorpt_coefficient_mu    10.838
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_correction_T_min  0.384
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -4 -3 0.0281
4 6 -1 0.0180
-5 2 3 0.0767
-5 -5 1 0.0485
4 6 4 0.0243
3 6 6 0.0328
-5 -5 -5 0.0283
0 -5 -6 0.0193
-2 0 7 0.0588
-2 4 -5 0.0711
5 -2 0 0.0370

_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.8038 -4.3152 -2.9470 -0.0599 -0.2502 0.9663
4.3815 6.2102 -0.5254 0.2308 0.9618 0.1471
-4.5135 1.5323 3.0387 -0.0391 -0.1626 -0.9859
-5.2100 -4.7265 1.4619 -0.2079 -0.8661 -0.4546
4.4111 6.3981 3.5597 -0.1821 0.9821 -0.0474
2.9803 5.8621 6.3949 -0.4471 0.8231 -0.3502
-5.0980 -4.8829 -5.2582 0.4736 -0.8721 -0.1232
0.1698 -5.3766 -5.9411 0.2977 -0.5479 0.7818
-2.4903 -0.2043 7.4504 -0.6793 -0.2015 -0.7056
-2.4237 3.9370 -4.6869 0.8121 0.2405 -0.5317
4.6083 -2.3732 0.0829 -0.3361 0.0804 0.9384

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13583
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.686
_diffrn_reflns_theta_min         3.231
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  37.00   0.50    0.05    --  -39.20  91.00-123.00  166
  2  ω    -35.00  36.00   0.50    0.05    --  -39.20  57.00-150.00  142
  3  ω    -68.00 -17.00   0.50    0.14    --  -94.50  30.00-180.00  102
  4  ω    -92.00 -10.00   0.50    0.05    --  -39.20 125.00-120.00  164
  5  ω    -91.00 -31.00   0.50    0.14    --  -94.50 125.00 -30.00  120
  6  ω    -69.00 -17.00   0.50    0.14    --  -94.50  30.00  60.00  104
  7  ω    -59.00 -19.00   0.50    0.05    --  -39.20 -77.00 150.00   80
  8  ω    -13.00  78.00   0.50    0.05    --   39.20 -91.00 123.00  182
  9  ω     77.00 144.00   0.50    0.14    --  109.49 -91.00 123.00  134
 10  ω     77.00 108.00   0.50    0.14    --  109.49 -94.00  60.00   62
 11  ω     42.00  99.00   0.50    0.14    --  109.49-125.00  90.00  114
 12  ω     30.00  74.00   0.50    0.14    --  109.49 -45.00  60.00   88
 13  ω     33.00  75.00   0.50    0.14    --  109.49 -45.00 120.00   84
 14  ω     32.00  68.00   0.50    0.14    --  109.49 -45.00 150.00   72
 15  ω     32.00  61.00   0.50    0.14    --  109.49 -45.00  90.00   58
 16  ω     77.00 173.00   0.50    0.14    --  109.49  30.00  90.00  192
 17  ω    140.00 177.00   0.50    0.14    --  109.49 125.00 -60.00   74
 18  ω    146.00 172.00   0.50    0.14    --  109.49 125.00-150.00   52
 19  ω    109.00 154.00   0.50    0.14    --  109.49  91.00-123.00   90
 20  ω     98.00 125.00   0.50    0.14    --  109.49 125.00 -30.00   54
 21  ω     93.00 118.00   0.50    0.14    --  109.49 125.00 -60.00   50
 22  ω     92.00 176.00   0.50    0.14    --  109.49 125.00  90.00  168
 23  ω     51.00  77.00   0.50    0.14    --  109.49 -45.00-120.00   52
 24  ω     53.00  79.00   0.50    0.14    --  109.49 -94.00 -90.00   52
 25  ω     40.00 116.00   0.50    0.14    --  109.49-125.00 -60.00  152
 26  ω     27.00  52.00   0.50    0.14    --  109.49 -30.00 -90.00   50
 27  ω     27.00  68.00   0.50    0.14    --  109.49 -30.00 -30.00   82
 28  ω     27.00  69.00   0.50    0.14    --  109.49 -30.00-120.00   84
 29  ω     32.00  68.00   0.50    0.14    --  109.49 -30.00-180.00   72
 30  ω     37.00  73.00   0.50    0.14    --  109.49 -45.00-180.00   72
 31  ω     32.00 117.00   0.50    0.14    --  109.49-125.00  30.00  170
 32  ω    -93.00 -66.00   0.50    0.14    --  -94.50 -45.00  30.00   54
 33  ω   -108.00 -83.00   0.50    0.05    --  -39.20-125.00  90.00   50
 34  ω   -115.00 -64.00   0.50    0.05    --  -39.20 -77.00 150.00  102
 35  ω   -124.00 -99.00   0.50    0.14    --  -94.50 -91.00 123.00   50
 36  ω   -172.00 -96.00   0.50    0.14    --  -94.50 -45.00  30.00  152
 37  ω   -108.00 -70.00   0.50    0.05    --  -39.20-125.00 -90.00   76
 38  ω   -110.00 -71.00   0.50    0.05    --  -39.20-125.00-120.00   78
 39  ω   -125.00-100.00   0.50    0.14    --  -94.50  91.00-123.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0414047000
_diffrn_orient_matrix_UB_12      0.0576279000
_diffrn_orient_matrix_UB_13      -0.1034411000
_diffrn_orient_matrix_UB_21      0.0712904000
_diffrn_orient_matrix_UB_22      0.1045488000
_diffrn_orient_matrix_UB_23      -0.0003535000
_diffrn_orient_matrix_UB_31      0.1574712000
_diffrn_orient_matrix_UB_32      -0.0911793000
_diffrn_orient_matrix_UB_33      -0.0445721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4941
_reflns_number_total             5254
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.096
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0196P)²+2.6299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0739
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C32(H32A,H32B), C31(H31A,H31B), C13(H13A,
 H13B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C4(H4), C23(H23), C9(H9), C8(H8), C5(H5), C29(H29), C25(H25),
 C26(H26), C28(H28), C24(H24), C27(H27), C7(H7)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.63240(2) 0.67590(2) 0.75916(2) 0.02332(7) Uani 1 1 d . . . . .
Cl1 Cl 0.52395(12) 0.89682(9) 0.80481(7) 0.0293(2) Uani 1 1 d . . . . .
N21 N 0.6829(4) 0.5627(3) 0.8942(2) 0.0253(7) Uani 1 1 d . . . . .
N1 N 0.5987(4) 0.7589(3) 0.6185(2) 0.0233(7) Uani 1 1 d . . . . .
C1A C 0.7345(5) 0.7392(4) 0.5568(3) 0.0234(8) Uani 1 1 d . . . . .
C10 C 0.8498(5) 0.6095(4) 0.6982(3) 0.0245(8) Uani 1 1 d . . . . .
C21A C 0.6664(5) 0.4431(4) 0.8987(3) 0.0288(9) Uani 1 1 d . . . . .
C6 C 1.0224(5) 0.6921(4) 0.4412(3) 0.0291(9) Uani 1 1 d . . . . .
H6 H 1.117765 0.678875 0.402761 0.035 Uiso 1 1 calc R . . . .
C3 C 0.4640(5) 0.8688(4) 0.4837(3) 0.0267(8) Uani 1 1 d . . . . .
H3 H 0.370530 0.910853 0.459277 0.032 Uiso 1 1 calc R . . . .
C30A C 0.6281(5) 0.4158(4) 0.8138(3) 0.0282(8) Uani 1 1 d . . . . .
C10A C 0.8703(5) 0.6596(4) 0.5991(3) 0.0251(8) Uani 1 1 d . . . . .
C4A C 0.7412(5) 0.7883(4) 0.4574(3) 0.0243(8) Uani 1 1 d . . . . .
C6A C 1.0164(5) 0.6365(4) 0.5422(3) 0.0258(8) Uani 1 1 d . . . . .
C2 C 0.4643(5) 0.8186(4) 0.5832(3) 0.0258(8) Uani 1 1 d . . . . .
C4 C 0.6007(5) 0.8563(4) 0.4217(3) 0.0279(8) Uani 1 1 d . . . . .
H4 H 0.599057 0.892973 0.356868 0.033 Uiso 1 1 calc R . . . .
C23 C 0.7541(5) 0.4984(5) 1.0549(3) 0.0332(9) Uani 1 1 d . . . . .
H23 H 0.784608 0.518401 1.107648 0.040 Uiso 1 1 calc R . . . .
C26A C 0.6068(5) 0.2964(4) 0.8135(3) 0.0317(9) Uani 1 1 d . . . . .
C9 C 0.9799(5) 0.5285(4) 0.7401(3) 0.0286(8) Uani 1 1 d . . . . .
H9 H 0.970305 0.489615 0.804208 0.034 Uiso 1 1 calc R . . . .
C24A C 0.6886(5) 0.3505(4) 0.9811(3) 0.0303(9) Uani 1 1 d . . . . .
C8 C 1.1269(5) 0.5060(4) 0.6839(3) 0.0300(9) Uani 1 1 d . . . . .
H8 H 1.213956 0.454267 0.712921 0.036 Uiso 1 1 calc R . . . .
C11 C 0.3205(5) 0.8244(5) 0.6539(3) 0.0314(9) Uani 1 1 d . . . . .
H11A H 0.316303 0.872364 0.706528 0.038 Uiso 1 1 calc R . . . .
H11B H 0.329945 0.736109 0.682430 0.038 Uiso 1 1 calc R . . . .
C5 C 0.8918(5) 0.7632(4) 0.4010(3) 0.0310(9) Uani 1 1 d . . . . .
H5 H 0.899955 0.796609 0.335429 0.037 Uiso 1 1 calc R . . . .
C30 C 0.6124(4) 0.5120(4) 0.7327(3) 0.0259(8) Uani 1 1 d . . . . .
C29 C 0.5719(5) 0.4872(4) 0.6503(3) 0.0287(8) Uani 1 1 d . . . . .
H29 H 0.558978 0.549072 0.595646 0.034 Uiso 1 1 calc R . . . .
C12 C 0.1680(5) 0.8859(4) 0.6131(3) 0.0302(9) Uani 1 1 d . . . . .
H12A H 0.169127 0.837984 0.561211 0.036 Uiso 1 1 calc R . . . .
H12B H 0.155622 0.974876 0.585183 0.036 Uiso 1 1 calc R . . . .
C25 C 0.6665(6) 0.2302(5) 0.9795(3) 0.0362(10) Uani 1 1 d . . . . .
H25 H 0.678716 0.169105 1.034642 0.043 Uiso 1 1 calc R . . . .
C26 C 0.6283(5) 0.2036(5) 0.8997(4) 0.0355(10) Uani 1 1 d . . . . .
H26 H 0.615633 0.124324 0.900455 0.043 Uiso 1 1 calc R . . . .
C32 C 0.8259(6) 0.7346(5) 1.0449(3) 0.0349(10) Uani 1 1 d . . . . .
H32A H 0.750078 0.738097 1.102846 0.042 Uiso 1 1 calc R . . . .
H32B H 0.918886 0.661412 1.057431 0.042 Uiso 1 1 calc R . . . .
C22 C 0.7312(5) 0.5892(4) 0.9691(3) 0.0305(9) Uani 1 1 d . . . . .
C28 C 0.5499(5) 0.3684(5) 0.6488(3) 0.0329(9) Uani 1 1 d . . . . .
H28 H 0.522939 0.353406 0.592680 0.040 Uiso 1 1 calc R . . . .
C24 C 0.7320(6) 0.3826(5) 1.0608(3) 0.0361(10) Uani 1 1 d . . . . .
H24 H 0.745790 0.324880 1.117769 0.043 Uiso 1 1 calc R . . . .
C27 C 0.5673(5) 0.2748(4) 0.7277(4) 0.0329(9) Uani 1 1 d . . . . .
H27 H 0.553121 0.197148 0.724696 0.040 Uiso 1 1 calc R . . . .
C7 C 1.1460(5) 0.5581(4) 0.5874(3) 0.0304(9) Uani 1 1 d . . . . .
H7 H 1.244491 0.541173 0.552501 0.036 Uiso 1 1 calc R . . . .
C34 C 0.9109(6) 0.8900(5) 1.1132(4) 0.0408(11) Uani 1 1 d . . . . .
H34A H 0.938852 0.966628 1.095449 0.061 Uiso 1 1 calc GR . . . .
H34B H 0.997928 0.817712 1.133667 0.061 Uiso 1 1 calc GR . . . .
H34C H 0.826940 0.904875 1.165874 0.061 Uiso 1 1 calc GR . . . .
C31 C 0.7642(6) 0.7132(5) 0.9590(3) 0.0363(10) Uani 1 1 d . . . . .
H31A H 0.669791 0.785836 0.948637 0.044 Uiso 1 1 calc R . . . .
H31B H 0.838486 0.715100 0.900970 0.044 Uiso 1 1 calc R . . . .
C13 C 0.0311(5) 0.8860(5) 0.6924(4) 0.0357(10) Uani 1 1 d . . . . .
H13A H 0.037342 0.796689 0.714865 0.043 Uiso 1 1 calc R . . . .
H13B H 0.037158 0.924659 0.747658 0.043 Uiso 1 1 calc R . . . .
C14 C -0.1226(6) 0.9609(5) 0.6556(4) 0.0440(12) Uani 1 1 d . . . . .
H14A H -0.126826 0.926036 0.598629 0.066 Uiso 1 1 calc GR . . . .
H14B H -0.133562 1.051192 0.639129 0.066 Uiso 1 1 calc GR . . . .
H14C H -0.204785 0.953000 0.705691 0.066 Uiso 1 1 calc GR . . . .
C33 C 0.8619(7) 0.8598(5) 1.0255(4) 0.0402(11) Uani 1 1 d . . . . .
H33A H 0.771257 0.931595 1.007152 0.048 Uiso 1 1 calc R . . . .
H33B H 0.943849 0.852879 0.970795 0.048 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 Cl1 2.4341(10) . ?
Ir1 N21 2.112(3) . ?
Ir1 N1 2.057(3) . ?
Ir1 C10 1.975(4) . ?
Ir1 C30 2.001(4) . ?
N21 C21A 1.384(6) . ?
N21 C22 1.336(6) . ?
N1 C1A 1.367(5) . ?
N1 C2 1.338(5) . ?
C1A C10A 1.429(6) . ?
C1A C4A 1.403(5) . ?
C10 C10A 1.409(6) . ?
C10 C9 1.390(6) . ?
C21A C30A 1.419(6) . ?
C21A C24A 1.398(6) . ?
C6 H6 0.9300 . ?
C6 C6A 1.442(6) . ?
C6 C5 1.358(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.410(6) . ?
C3 C4 1.383(6) . ?
C30A C26A 1.413(6) . ?
C30A C30 1.407(6) . ?
C10A C6A 1.410(6) . ?
C4A C4 1.398(6) . ?
C4A C5 1.440(6) . ?
C6A C7 1.402(6) . ?
C2 C11 1.506(6) . ?
C4 H4 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.424(6) . ?
C23 C24 1.364(7) . ?
C26A C26 1.439(7) . ?
C26A C27 1.407(7) . ?
C9 H9 0.9300 . ?
C9 C8 1.414(6) . ?
C24A C25 1.431(7) . ?
C24A C24 1.402(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.382(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.520(6) . ?
C5 H5 0.9300 . ?
C30 C29 1.384(6) . ?
C29 H29 0.9300 . ?
C29 C28 1.414(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.534(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.347(7) . ?
C26 H26 0.9300 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C31 1.521(6) . ?
C32 C33 1.518(7) . ?
C22 C31 1.499(7) . ?
C28 H28 0.9300 . ?
C28 C27 1.369(7) . ?
C24 H24 0.9300 . ?
C27 H27 0.9300 . ?
C7 H7 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C34 C33 1.521(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.516(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?

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
N21 Ir1 Cl1 102.27(10) . . ?
N1 Ir1 Cl1 86.68(9) . . ?
N1 Ir1 N21 171.04(13) . . ?
C10 Ir1 Cl1 119.21(12) . . ?
C10 Ir1 N21 92.65(15) . . ?
C10 Ir1 N1 82.37(15) . . ?
C10 Ir1 C30 87.75(16) . . ?
C30 Ir1 Cl1 152.28(11) . . ?
C30 Ir1 N21 81.26(16) . . ?
C30 Ir1 N1 91.07(15) . . ?
C21A N21 Ir1 111.1(3) . . ?
C22 N21 Ir1 129.7(3) . . ?
C22 N21 C21A 119.2(4) . . ?
C1A N1 Ir1 112.4(3) . . ?
C2 N1 Ir1 127.5(3) . . ?
C2 N1 C1A 119.9(3) . . ?
N1 C1A C10A 115.4(4) . . ?
N1 C1A C4A 122.9(4) . . ?
C4A C1A C10A 121.7(4) . . ?
C10A C10 Ir1 112.5(3) . . ?
C9 C10 Ir1 129.4(3) . . ?
C9 C10 C10A 118.0(4) . . ?
N21 C21A C30A 116.7(4) . . ?
N21 C21A C24A 123.0(4) . . ?
C24A C21A C30A 120.3(4) . . ?
C6A C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C6A 121.5(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.0(4) . . ?
C26A C30A C21A 119.9(4) . . ?
C30 C30A C21A 117.0(4) . . ?
C30 C30A C26A 123.0(4) . . ?
C10 C10A C1A 117.0(4) . . ?
C10 C10A C6A 123.2(4) . . ?
C6A C10A C1A 119.8(4) . . ?
C1A C4A C5 117.3(4) . . ?
C4 C4A C1A 117.0(4) . . ?
C4 C4A C5 125.7(4) . . ?
C10A C6A C6 118.0(4) . . ?
C7 C6A C6 124.5(4) . . ?
C7 C6A C10A 117.5(4) . . ?
N1 C2 C3 119.5(4) . . ?
N1 C2 C11 116.6(4) . . ?
C3 C2 C11 123.8(4) . . ?
C3 C4 C4A 119.5(4) . . ?
C3 C4 H4 120.3 . . ?
C4A C4 H4 120.3 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C24 C23 C22 120.9(4) . . ?
C30A C26A C26 118.6(4) . . ?
C27 C26A C30A 117.7(4) . . ?
C27 C26A C26 123.8(4) . . ?
C10 C9 H9 120.5 . . ?
C10 C9 C8 119.1(4) . . ?
C8 C9 H9 120.5 . . ?
C21A C24A C25 118.9(4) . . ?
C21A C24A C24 116.9(4) . . ?
C24 C24A C25 124.1(4) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 C9 122.4(4) . . ?
C7 C8 H8 118.8 . . ?
C2 C11 H11A 108.1 . . ?
C2 C11 H11B 108.1 . . ?
C2 C11 C12 116.8(4) . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C6 C5 C4A 121.7(4) . . ?
C6 C5 H5 119.2 . . ?
C4A C5 H5 119.2 . . ?
C30A C30 Ir1 113.6(3) . . ?
C29 C30 Ir1 128.7(3) . . ?
C29 C30 C30A 117.3(4) . . ?
C30 C29 H29 119.8 . . ?
C30 C29 C28 120.4(4) . . ?
C28 C29 H29 119.8 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C11 C12 C13 111.6(4) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C24A C25 H25 119.3 . . ?
C26 C25 C24A 121.4(4) . . ?
C26 C25 H25 119.3 . . ?
C26A C26 H26 119.6 . . ?
C25 C26 C26A 120.8(4) . . ?
C25 C26 H26 119.6 . . ?
H32A C32 H32B 107.9 . . ?
C31 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C33 C32 H32B 109.3 . . ?
C33 C32 C31 111.8(4) . . ?
N21 C22 C23 119.8(4) . . ?
N21 C22 C31 118.7(4) . . ?
C23 C22 C31 121.6(4) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 C29 121.7(4) . . ?
C27 C28 H28 119.1 . . ?
C23 C24 C24A 120.0(4) . . ?
C23 C24 H24 120.0 . . ?
C24A C24 H24 120.0 . . ?
C26A C27 H27 120.1 . . ?
C28 C27 C26A 119.8(4) . . ?
C28 C27 H27 120.1 . . ?
C6A C7 H7 120.1 . . ?
C8 C7 C6A 119.8(4) . . ?
C8 C7 H7 120.1 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
C32 C31 H31A 108.3 . . ?
C32 C31 H31B 108.3 . . ?
C22 C31 C32 116.1(4) . . ?
C22 C31 H31A 108.3 . . ?
C22 C31 H31B 108.3 . . ?
H31A C31 H31B 107.4 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.2(4) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C32 C33 C34 113.1(4) . . ?
C32 C33 H33A 108.9 . . ?
C32 C33 H33B 108.9 . . ?
C34 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
H33A C33 H33B 107.8 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.659
_oxdiff_exptl_absorpt_empirical_full_min 0.754
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_takimoto_autored
_database_code_depnum_ccdc_archive 'CCDC 2099501'
loop_
_audit_author_name
_audit_author_address
'Kazuyoshi Takimoto'
;Ehime University
Japan
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C46 H40 Ir N4, Cl, 1.31(C H4 O), C0.69 H3.07 O0.69'
_chemical_formula_sum            'C48 H48.31 Cl Ir N4 O2'
_chemical_formula_weight         940.86
_chemical_melting_point          ?
_chemical_oxdiff_formula         Ir1Cl1N4C46H40
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3729(4)
_cell_length_b                   16.0231(3)
_cell_length_c                   17.1143(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.488(3)
_cell_angle_gamma                90
_cell_volume                     4081.56(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    35563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.1160
_cell_measurement_theta_min      1.7560
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.729
_exptl_absorpt_coefficient_mu    3.381
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1897
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            68718
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         1.768
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00  90.00  360
  3  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00 180.00  360
  4  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00 270.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0399883000
_diffrn_orient_matrix_UB_12      -0.0233200000
_diffrn_orient_matrix_UB_13      -0.0146633000
_diffrn_orient_matrix_UB_21      -0.0255415000
_diffrn_orient_matrix_UB_22      0.0373098000
_diffrn_orient_matrix_UB_23      -0.0039609000
_diffrn_orient_matrix_UB_31      0.0044439000
_diffrn_orient_matrix_UB_32      0.0048332000
_diffrn_orient_matrix_UB_33      -0.0400185000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8091
_reflns_number_total             9849
_reflns_odcompleteness_completeness 94.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.06
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.166
_refine_diff_density_min         -2.012
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         9849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0256P)²+9.0291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(O3)=Sof(H3)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=1-FVAR(1)
 Sof(O2)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C31(H31A,H31B), C32(H32A,
 H32B), C33(H33A,H33B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C21(H21),
 C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C35(H35), C36(H36),
  C37(H37), C39(H39), C40(H40), C42(H42), C43(H43), C44(H44)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C), C47(H47A,H47B,H47C), C48(H48A,H48B,
 H48C), C49(H49A,H49B,H49C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.28049(2) 0.64989(2) 0.64859(2) 0.01355(5) Uani 1 1 d . . . . .
N1 N 0.4175(2) 0.6750(2) 0.6568(2) 0.0173(8) Uani 1 1 d . . . . .
N2 N 0.1463(2) 0.6459(2) 0.6567(2) 0.0180(7) Uani 1 1 d . . . . .
N3 N 0.2668(2) 0.5164(2) 0.6279(2) 0.0178(8) Uani 1 1 d . . . . .
N4 N 0.2699(2) 0.6383(2) 0.52047(19) 0.0155(7) Uani 1 1 d . . . . .
C1 C 0.4323(3) 0.7601(3) 0.6501(2) 0.0201(10) Uani 1 1 d . . . . .
C2 C 0.3577(3) 0.8136(3) 0.6471(2) 0.0216(10) Uani 1 1 d . . . . .
C3 C 0.2771(3) 0.7756(3) 0.6516(3) 0.0190(9) Uani 1 1 d . . . . .
C4 C 0.2052(3) 0.8296(3) 0.6517(3) 0.0245(11) Uani 1 1 d . . . . .
H4 H 0.150199 0.807476 0.654619 0.029 Uiso 1 1 calc R . . . .
C5 C 0.2152(4) 0.9165(3) 0.6475(3) 0.0306(12) Uani 1 1 d . . . . .
H5 H 0.166362 0.950692 0.647954 0.037 Uiso 1 1 calc R . . . .
C6 C 0.2946(4) 0.9525(3) 0.6429(3) 0.0330(13) Uani 1 1 d . . . . .
H6 H 0.299251 1.010241 0.640093 0.040 Uiso 1 1 calc R . . . .
C7 C 0.3694(4) 0.9017(3) 0.6423(3) 0.0274(12) Uani 1 1 d . . . . .
C8 C 0.4535(4) 0.9330(3) 0.6360(3) 0.0331(13) Uani 1 1 d . . . . .
H8 H 0.460242 0.990025 0.629415 0.040 Uiso 1 1 calc R . . . .
C9 C 0.5243(4) 0.8818(4) 0.6395(3) 0.0357(14) Uani 1 1 d . . . . .
H9 H 0.578847 0.904325 0.635580 0.043 Uiso 1 1 calc R . . . .
C10 C 0.5169(3) 0.7934(3) 0.6491(3) 0.0264(11) Uani 1 1 d . . . . .
C11 C 0.5898(4) 0.7380(4) 0.6613(3) 0.0361(13) Uani 1 1 d . . . . .
H11 H 0.646923 0.757285 0.661650 0.043 Uiso 1 1 calc R . . . .
C12 C 0.5755(3) 0.6559(4) 0.6726(3) 0.0340(12) Uani 1 1 d . . . . .
H12 H 0.624224 0.619525 0.682572 0.041 Uiso 1 1 calc R . . . .
C13 C 0.4893(3) 0.6236(3) 0.6697(3) 0.0232(10) Uani 1 1 d . . . . .
C14 C 0.4811(3) 0.5323(3) 0.6817(3) 0.0235(10) Uani 1 1 d . . . . .
H14A H 0.424213 0.521427 0.694669 0.028 Uiso 1 1 calc R . . . .
H14B H 0.528622 0.514907 0.727557 0.028 Uiso 1 1 calc R . . . .
C15 C 0.4862(3) 0.4790(3) 0.6080(3) 0.0235(10) Uani 1 1 d . . . . .
H15A H 0.434702 0.491552 0.563685 0.028 Uiso 1 1 calc R . . . .
H15B H 0.539906 0.493935 0.591237 0.028 Uiso 1 1 calc R . . . .
C16 C 0.4878(3) 0.3859(3) 0.6254(3) 0.0270(11) Uani 1 1 d . . . . .
H16A H 0.436649 0.371711 0.646499 0.032 Uiso 1 1 calc R . . . .
H16B H 0.541927 0.372512 0.666502 0.032 Uiso 1 1 calc R . . . .
C17 C 0.4848(3) 0.3335(3) 0.5502(3) 0.0344(13) Uani 1 1 d . . . . .
H17A H 0.427151 0.339708 0.512745 0.052 Uiso 1 1 calc GR . . . .
H17B H 0.494459 0.275868 0.565175 0.052 Uiso 1 1 calc GR . . . .
H17C H 0.530915 0.352008 0.525370 0.052 Uiso 1 1 calc GR . . . .
C18 C 0.1400(3) 0.6298(3) 0.7351(3) 0.0199(10) Uani 1 1 d . . . . .
C19 C 0.2235(3) 0.6209(3) 0.7940(2) 0.0178(9) Uani 1 1 d . . . . .
C20 C 0.3034(3) 0.6353(3) 0.7688(2) 0.0172(9) Uani 1 1 d . . . . .
C21 C 0.3843(3) 0.6288(3) 0.8275(2) 0.0194(10) Uani 1 1 d . . . . .
H21 H 0.438233 0.638904 0.813833 0.023 Uiso 1 1 calc R . . . .
C22 C 0.3848(3) 0.6068(3) 0.9080(3) 0.0232(10) Uani 1 1 d . . . . .
H22 H 0.439409 0.602497 0.946370 0.028 Uiso 1 1 calc R . . . .
C23 C 0.3067(3) 0.5917(3) 0.9304(3) 0.0259(11) Uani 1 1 d . . . . .
H23 H 0.309156 0.574899 0.982948 0.031 Uiso 1 1 calc R . . . .
C24 C 0.2223(3) 0.6015(3) 0.8746(3) 0.0221(10) Uani 1 1 d . . . . .
C25 C 0.1378(3) 0.5950(3) 0.8948(3) 0.0293(11) Uani 1 1 d . . . . .
H25 H 0.136773 0.581494 0.947446 0.035 Uiso 1 1 calc R . . . .
C26 C 0.0594(3) 0.6079(3) 0.8392(3) 0.0312(12) Uani 1 1 d . . . . .
H26 H 0.005527 0.604983 0.854520 0.037 Uiso 1 1 calc R . . . .
C27 C 0.0583(3) 0.6262(3) 0.7564(3) 0.0265(11) Uani 1 1 d . . . . .
C28 C -0.0210(3) 0.6434(4) 0.6971(3) 0.0378(13) Uani 1 1 d . . . . .
H28 H -0.076764 0.641970 0.709071 0.045 Uiso 1 1 calc R . . . .
C29 C -0.0135(3) 0.6623(4) 0.6206(3) 0.0345(13) Uani 1 1 d . . . . .
H29 H -0.065262 0.674533 0.580853 0.041 Uiso 1 1 calc R . . . .
C30 C 0.0697(3) 0.6639(3) 0.6006(3) 0.0234(10) Uani 1 1 d . . . . .
C31 C 0.0690(3) 0.6894(3) 0.5159(3) 0.0224(10) Uani 1 1 d . . . . .
H31A H 0.129450 0.705296 0.514366 0.027 Uiso 1 1 calc R . . . .
H31B H 0.030940 0.738185 0.501579 0.027 Uiso 1 1 calc R . . . .
C32 C 0.0354(3) 0.6207(3) 0.4526(3) 0.0271(11) Uani 1 1 d . . . . .
H32A H 0.078360 0.575167 0.461316 0.033 Uiso 1 1 calc R . . . .
H32B H -0.021423 0.598941 0.458667 0.033 Uiso 1 1 calc R . . . .
C33 C 0.0232(3) 0.6550(4) 0.3672(3) 0.0355(12) Uani 1 1 d . . . . .
H33A H -0.024319 0.696436 0.356757 0.043 Uiso 1 1 calc R . . . .
H33B H 0.078233 0.682487 0.363298 0.043 Uiso 1 1 calc R . . . .
C34 C 0.0000(4) 0.5866(4) 0.3032(3) 0.0542(18) Uani 1 1 d . . . . .
H34A H -0.008990 0.611030 0.250580 0.081 Uiso 1 1 calc GR . . . .
H34B H -0.054063 0.558825 0.307272 0.081 Uiso 1 1 calc GR . . . .
H34C H 0.048274 0.547037 0.311623 0.081 Uiso 1 1 calc GR . . . .
C35 C 0.2586(3) 0.4573(3) 0.6810(3) 0.0236(10) Uani 1 1 d . . . . .
H35 H 0.264738 0.472379 0.734530 0.028 Uiso 1 1 calc R . . . .
C36 C 0.2410(3) 0.3734(3) 0.6589(3) 0.0267(11) Uani 1 1 d . . . . .
H36 H 0.234585 0.334204 0.697118 0.032 Uiso 1 1 calc R . . . .
C37 C 0.2332(3) 0.3500(3) 0.5806(3) 0.0295(11) Uani 1 1 d . . . . .
H37 H 0.222168 0.294562 0.565337 0.035 Uiso 1 1 calc R . . . .
C38 C 0.2422(3) 0.4103(3) 0.5231(3) 0.0206(10) Uani 1 1 d . . . . .
C39 C 0.2366(3) 0.3919(3) 0.4400(3) 0.0260(11) Uani 1 1 d . . . . .
H39 H 0.227772 0.336990 0.422121 0.031 Uiso 1 1 calc R . . . .
C40 C 0.2439(3) 0.4521(3) 0.3871(3) 0.0269(11) Uani 1 1 d . . . . .
H40 H 0.239817 0.438050 0.333558 0.032 Uiso 1 1 calc R . . . .
C41 C 0.2578(3) 0.5376(3) 0.4120(2) 0.0190(9) Uani 1 1 d . . . . .
C42 C 0.2679(3) 0.6035(3) 0.3599(3) 0.0231(10) Uani 1 1 d . . . . .
H42 H 0.266474 0.592695 0.306219 0.028 Uiso 1 1 calc R . . . .
C43 C 0.2797(3) 0.6827(3) 0.3892(3) 0.0252(10) Uani 1 1 d . . . . .
H43 H 0.287838 0.726247 0.355800 0.030 Uiso 1 1 calc R . . . .
C44 C 0.2795(3) 0.6988(3) 0.4700(3) 0.0213(10) Uani 1 1 d . . . . .
H44 H 0.286422 0.753462 0.488722 0.026 Uiso 1 1 calc R . . . .
C45 C 0.2610(3) 0.5581(3) 0.4931(2) 0.0163(9) Uani 1 1 d . . . . .
C46 C 0.2561(3) 0.4938(3) 0.5496(3) 0.0173(9) Uani 1 1 d . . . . .
Cl1 Cl 0.19578(9) 1.15607(8) 0.68690(8) 0.0375(3) Uani 1 1 d . . . . .
O1 O 0.1116(3) 1.1719(3) 0.5028(3) 0.0646(14) Uani 1 1 d . . . . .
H1 H 0.131088 1.169052 0.551903 0.097 Uiso 1 1 calc GR . . . .
C47 C 0.0612(6) 1.1014(4) 0.4752(5) 0.079(3) Uani 1 1 d . . . . .
H47A H 0.081549 1.055991 0.511849 0.119 Uiso 1 1 calc GR . . . .
H47B H 0.068204 1.086856 0.422705 0.119 Uiso 1 1 calc GR . . . .
H47C H -0.000934 1.112413 0.471996 0.119 Uiso 1 1 calc GR . . . .
O2 O 0.3786(3) 1.1543(3) 0.6212(3) 0.0261(12) Uani 0.690(6) 1 d . . P A 1
H2 H 0.336673 1.166584 0.640669 0.039 Uiso 1 1 calc GR . . A 1
C48 C 0.3453(5) 1.1409(5) 0.5357(5) 0.040(2) Uani 0.690(6) 1 d . . P A 1
H48A H 0.303649 1.095202 0.526462 0.060 Uiso 0.690(6) 1 calc GR . P A 1
H48B H 0.394645 1.128185 0.512644 0.060 Uiso 0.690(6) 1 calc GR . P A 1
H48C H 0.315565 1.190466 0.511018 0.060 Uiso 0.690(6) 1 calc GR . P A 1
O3 O 0.1998(7) 0.2997(9) 0.8444(8) 0.052(4) Uani 0.310(6) 1 d . . P A 2
H3 H 0.152241 0.325490 0.833955 0.078 Uiso 0.310(6) 1 calc GR . P A 2
C49 C 0.2649(13) 0.3283(12) 0.9429(10) 0.042(5) Uani 0.310(6) 1 d . . P A 2
H49A H 0.226006 0.350786 0.973613 0.064 Uiso 0.310(6) 1 calc GR . P A 2
H49B H 0.308535 0.369618 0.938046 0.064 Uiso 0.310(6) 1 calc GR . P A 2
H49C H 0.295145 0.279942 0.969764 0.064 Uiso 0.310(6) 1 calc GR . P A 2


_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 2.114(4) . ?
Ir1 N2 2.103(3) . ?
Ir1 N3 2.170(4) . ?
Ir1 N4 2.166(3) . ?
Ir1 C3 2.016(4) . ?
Ir1 C20 2.013(4) . ?
N1 C1 1.391(6) . ?
N1 C13 1.352(6) . ?
N2 C18 1.393(5) . ?
N2 C30 1.352(5) . ?
N3 C35 1.340(5) . ?
N3 C46 1.357(5) . ?
N4 C44 1.331(5) . ?
N4 C45 1.363(5) . ?
C1 C2 1.423(7) . ?
C1 C10 1.410(6) . ?
C2 C3 1.401(6) . ?
C2 C7 1.427(6) . ?
C3 C4 1.403(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.405(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.410(7) . ?
C7 C8 1.416(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.353(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.433(7) . ?
C10 C11 1.404(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.356(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.412(7) . ?
C13 C14 1.487(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.541(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.520(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.528(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.427(6) . ?
C18 C27 1.392(6) . ?
C19 C20 1.419(6) . ?
C19 C24 1.418(6) . ?
C20 C21 1.393(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.421(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.371(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.414(7) . ?
C24 C25 1.429(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.352(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.444(6) . ?
C27 C28 1.405(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.376(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.405(6) . ?
C30 C31 1.502(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.542(6) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.529(7) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.527(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35 0.9300 . ?
C35 C36 1.403(6) . ?
C36 H36 0.9300 . ?
C36 C37 1.368(7) . ?
C37 H37 0.9300 . ?
C37 C38 1.409(7) . ?
C38 C39 1.435(6) . ?
C38 C46 1.412(6) . ?
C39 H39 0.9300 . ?
C39 C40 1.346(7) . ?
C40 H40 0.9300 . ?
C40 C41 1.435(7) . ?
C41 C42 1.414(6) . ?
C41 C45 1.414(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.360(7) . ?
C43 H43 0.9300 . ?
C43 C44 1.407(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.429(6) . ?
O1 H1 0.8200 . ?
O1 C47 1.384(8) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
O2 H2 0.8200 . ?
O2 C48 1.440(9) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
O3 H3 0.8200 . ?
O3 C49 1.79(2) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 N3 104.65(13) . . ?
N1 Ir1 N4 84.57(13) . . ?
N2 Ir1 N1 168.16(14) . . ?
N2 Ir1 N3 85.66(14) . . ?
N2 Ir1 N4 103.75(13) . . ?
N4 Ir1 N3 76.74(13) . . ?
C3 Ir1 N1 80.79(17) . . ?
C3 Ir1 N2 89.79(17) . . ?
C3 Ir1 N3 170.81(16) . . ?
C3 Ir1 N4 96.66(15) . . ?
C20 Ir1 N1 92.15(15) . . ?
C20 Ir1 N2 81.50(16) . . ?
C20 Ir1 N3 92.13(15) . . ?
C20 Ir1 N4 167.13(15) . . ?
C20 Ir1 C3 95.09(17) . . ?
C1 N1 Ir1 111.2(3) . . ?
C13 N1 Ir1 130.9(3) . . ?
C13 N1 C1 117.8(4) . . ?
C18 N2 Ir1 112.1(3) . . ?
C30 N2 Ir1 129.8(3) . . ?
C30 N2 C18 117.8(4) . . ?
C35 N3 Ir1 127.5(3) . . ?
C35 N3 C46 118.1(4) . . ?
C46 N3 Ir1 114.0(3) . . ?
C44 N4 Ir1 127.1(3) . . ?
C44 N4 C45 118.7(4) . . ?
C45 N4 Ir1 113.9(3) . . ?
N1 C1 C2 116.5(4) . . ?
N1 C1 C10 122.9(4) . . ?
C10 C1 C2 120.6(4) . . ?
C1 C2 C7 119.1(5) . . ?
C3 C2 C1 116.9(4) . . ?
C3 C2 C7 124.0(5) . . ?
C2 C3 Ir1 113.8(3) . . ?
C2 C3 C4 116.1(4) . . ?
C4 C3 Ir1 129.9(4) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(5) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(5) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 117.1(5) . . ?
C6 C7 C8 123.8(5) . . ?
C8 C7 C2 119.0(5) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.5(5) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.2(5) . . ?
C10 C9 H9 119.4 . . ?
C1 C10 C9 118.4(5) . . ?
C11 C10 C1 117.6(5) . . ?
C11 C10 C9 124.0(5) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.9(5) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 118.8 . . ?
C11 C12 C13 122.3(5) . . ?
C13 C12 H12 118.8 . . ?
N1 C13 C12 120.2(5) . . ?
N1 C13 C14 121.9(4) . . ?
C12 C13 C14 117.9(4) . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C13 C14 C15 114.1(4) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 112.6(4) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C15 C16 C17 112.2(4) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 115.5(4) . . ?
C27 C18 N2 123.0(4) . . ?
C27 C18 C19 121.5(4) . . ?
C20 C19 C18 117.6(4) . . ?
C24 C19 C18 118.7(4) . . ?
C24 C19 C20 123.6(4) . . ?
C19 C20 Ir1 112.7(3) . . ?
C21 C20 Ir1 129.9(3) . . ?
C21 C20 C19 117.0(4) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.3(4) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.5(4) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.7(4) . . ?
C24 C23 H23 119.6 . . ?
C19 C24 C25 119.0(4) . . ?
C23 C24 C19 116.7(4) . . ?
C23 C24 C25 124.3(4) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.5(4) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.7(4) . . ?
C27 C26 H26 119.6 . . ?
C18 C27 C26 118.4(4) . . ?
C18 C27 C28 118.7(4) . . ?
C28 C27 C26 122.9(4) . . ?
C27 C28 H28 121.1 . . ?
C29 C28 C27 117.7(4) . . ?
C29 C28 H28 121.1 . . ?
C28 C29 H29 118.8 . . ?
C28 C29 C30 122.4(4) . . ?
C30 C29 H29 118.8 . . ?
N2 C30 C29 120.4(4) . . ?
N2 C30 C31 122.6(4) . . ?
C29 C30 C31 116.9(4) . . ?
C30 C31 H31A 108.8 . . ?
C30 C31 H31B 108.8 . . ?
C30 C31 C32 113.8(4) . . ?
H31A C31 H31B 107.7 . . ?
C32 C31 H31A 108.8 . . ?
C32 C31 H31B 108.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C33 C32 C31 110.8(4) . . ?
C33 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
C32 C33 H33A 109.2 . . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C34 C33 C32 112.2(5) . . ?
C34 C33 H33A 109.2 . . ?
C34 C33 H33B 109.2 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N3 C35 H35 118.7 . . ?
N3 C35 C36 122.6(4) . . ?
C36 C35 H35 118.7 . . ?
C35 C36 H36 120.3 . . ?
C37 C36 C35 119.3(5) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 120.1 . . ?
C36 C37 C38 119.8(5) . . ?
C38 C37 H37 120.1 . . ?
C37 C38 C39 124.0(4) . . ?
C37 C38 C46 117.3(4) . . ?
C46 C38 C39 118.7(4) . . ?
C38 C39 H39 119.2 . . ?
C40 C39 C38 121.7(4) . . ?
C40 C39 H39 119.2 . . ?
C39 C40 H40 119.5 . . ?
C39 C40 C41 121.0(4) . . ?
C41 C40 H40 119.5 . . ?
C42 C41 C40 123.8(4) . . ?
C45 C41 C40 118.6(4) . . ?
C45 C41 C42 117.5(4) . . ?
C41 C42 H42 120.3 . . ?
C43 C42 C41 119.3(4) . . ?
C43 C42 H42 120.3 . . ?
C42 C43 H43 120.0 . . ?
C42 C43 C44 120.0(4) . . ?
C44 C43 H43 120.0 . . ?
N4 C44 C43 122.2(4) . . ?
N4 C44 H44 118.9 . . ?
C43 C44 H44 118.9 . . ?
N4 C45 C41 122.2(4) . . ?
N4 C45 C46 117.7(4) . . ?
C41 C45 C46 120.1(4) . . ?
N3 C46 C38 122.8(4) . . ?
N3 C46 C45 117.5(4) . . ?
C38 C46 C45 119.7(4) . . ?
C47 O1 H1 109.5 . . ?
O1 C47 H47A 109.5 . . ?
O1 C47 H47B 109.5 . . ?
O1 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C48 O2 H2 109.5 . . ?
O2 C48 H48A 109.5 . . ?
O2 C48 H48B 109.5 . . ?
O2 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C49 O3 H3 109.5 . . ?
O3 C49 H49A 109.5 . . ?
O3 C49 H49B 109.5 . . ?
O3 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.895
####################################################################### 
# 
# 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_takimoto
_database_code_depnum_ccdc_archive 'CCDC 2085213'
loop_
_audit_author_name
_audit_author_address
'Kazuyoshi Takimoto'
;Ehime University
Japan
;
_audit_update_record             
;
2021-05-22 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_audit_creation_date             2020-11-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H38 Cl Ir N2 O, C2 H6 O'
_chemical_formula_sum            'C38 H44 Cl Ir N2 O2'
_chemical_formula_weight         788.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         Ir1O1N2C28H34
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3674(4)
_cell_length_b                   11.2876(5)
_cell_length_c                   17.3082(6)
_cell_angle_alpha                99.175(3)
_cell_angle_beta                 100.384(3)
_cell_angle_gamma                113.623(4)
_cell_volume                     1593.84(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14272
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.2120
_cell_measurement_theta_min      2.0240
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.846
_exptl_absorpt_coefficient_mu    4.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.038
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00  90.00  360
  3  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00 180.00  360
  4  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00 270.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0462069000
_diffrn_orient_matrix_UB_12      -0.0360656000
_diffrn_orient_matrix_UB_13      -0.0047207000
_diffrn_orient_matrix_UB_21      -0.0300687000
_diffrn_orient_matrix_UB_22      -0.0158768000
_diffrn_orient_matrix_UB_23      -0.0428386000
_diffrn_orient_matrix_UB_31      0.0657869000
_diffrn_orient_matrix_UB_32      0.0590262000
_diffrn_orient_matrix_UB_33      -0.0010837000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6817
_reflns_number_total             7672
_reflns_odcompleteness_completeness 90.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.10
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.490
_refine_diff_density_min         -1.230
_refine_diff_density_rms         0.173
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7672
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+0.9054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0724
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.01
 C36-H1
 1.89072 with sigma of 0.02
 Ir1-H1
 2.89207 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C15(H15A,H15B), C33(H33A,H33B), C14(H14A,
 H14B), C16(H16A,H16B), C36(H36A,H36B), C38(H38A,H38B)
3.b Aromatic/amide H refined with riding coordinates:
 C29(H29), C28(H28), C6(H6), C25(H25), C26(H26), C23(H23), C8(H8), C4(H4),
 C5(H5), C11(H11), C22(H22), C12(H12), C9(H9), C21(H21)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C37(H37A,H37B,
 H37C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.78581(2) 0.37446(2) 0.71314(2) 0.01109(5) Uani 1 1 d D . . . .
Cl1 Cl 0.78003(12) 0.15336(10) 0.72640(6) 0.0170(2) Uani 1 1 d . . . . .
O1 O 0.5925(4) 0.3176(3) 0.78466(18) 0.0185(7) Uani 1 1 d D . . . .
H1 H 0.573(4) 0.248(2) 0.8039(19) 0.028 Uiso 1 1 d DR . . . .
N1 N 0.9399(4) 0.5168(3) 0.8233(2) 0.0129(7) Uani 1 1 d . . . . .
N2 N 0.6558(4) 0.2614(3) 0.5937(2) 0.0122(7) Uani 1 1 d . . . . .
O2 O 0.6048(4) 0.1202(3) 0.8585(2) 0.0312(8) Uani 1 1 d . . . . .
C19 C 0.9228(5) 0.3556(4) 0.5788(3) 0.0137(9) Uani 1 1 d . . . . .
C20 C 0.9678(5) 0.4235(4) 0.6620(3) 0.0158(9) Uani 1 1 d . . . . .
C29 C 0.4336(5) 0.1140(4) 0.4791(3) 0.0153(9) Uani 1 1 d . . . . .
H29 H 0.322627 0.062167 0.457579 0.018 Uiso 1 1 calc R . . . .
C27 C 0.6996(5) 0.1987(4) 0.4614(3) 0.0149(9) Uani 1 1 d . . . . .
C1 C 0.9383(5) 0.6391(4) 0.8260(3) 0.0138(9) Uani 1 1 d . . . . .
C28 C 0.5342(5) 0.1188(4) 0.4304(3) 0.0166(9) Uani 1 1 d . . . . .
H28 H 0.492072 0.068676 0.376515 0.020 Uiso 1 1 calc R . . . .
C18 C 0.7559(5) 0.2686(4) 0.5435(3) 0.0139(9) Uani 1 1 d . . . . .
C7 C 0.8270(5) 0.7685(4) 0.7572(3) 0.0160(9) Uani 1 1 d . . . . .
C2 C 0.8371(5) 0.6474(4) 0.7582(2) 0.0132(9) Uani 1 1 d . . . . .
C6 C 0.7273(5) 0.7721(4) 0.6872(3) 0.0166(9) Uani 1 1 d . . . . .
H6 H 0.718032 0.850327 0.684289 0.020 Uiso 1 1 calc R . . . .
C3 C 0.7526(5) 0.5317(4) 0.6926(2) 0.0121(8) Uani 1 1 d . . . . .
C24 C 1.0334(5) 0.3724(4) 0.5318(3) 0.0163(9) Uani 1 1 d . . . . .
C30 C 0.4947(5) 0.1861(4) 0.5614(3) 0.0137(9) Uani 1 1 d . . . . .
C25 C 0.9750(5) 0.2980(4) 0.4480(3) 0.0174(9) Uani 1 1 d . . . . .
H25 H 1.046739 0.306454 0.416077 0.021 Uiso 1 1 calc R . . . .
C31 C 0.3859(5) 0.1854(4) 0.6145(3) 0.0160(9) Uani 1 1 d . . . . .
H31A H 0.418763 0.277010 0.643532 0.019 Uiso 1 1 calc R . . . .
H31B H 0.401958 0.137652 0.654622 0.019 Uiso 1 1 calc R . . . .
C26 C 0.8155(5) 0.2156(4) 0.4158(3) 0.0181(9) Uani 1 1 d . . . . .
H26 H 0.780002 0.167869 0.361509 0.022 Uiso 1 1 calc R . . . .
C32 C 0.2045(5) 0.1222(4) 0.5712(3) 0.0172(9) Uani 1 1 d . . . . .
H32A H 0.188080 0.162807 0.527156 0.021 Uiso 1 1 calc R . . . .
H32B H 0.167044 0.027460 0.547832 0.021 Uiso 1 1 calc R . . . .
C23 C 1.1974(5) 0.4634(4) 0.5697(3) 0.0187(10) Uani 1 1 d . . . . .
H23 H 1.274537 0.476116 0.540664 0.022 Uiso 1 1 calc R . . . .
C8 C 0.9176(5) 0.8796(4) 0.8263(3) 0.0201(10) Uani 1 1 d . . . . .
H8 H 0.909296 0.959104 0.826758 0.024 Uiso 1 1 calc R . . . .
C10 C 1.0314(5) 0.7513(4) 0.8927(3) 0.0153(9) Uani 1 1 d . . . . .
C4 C 0.6561(5) 0.5410(4) 0.6256(3) 0.0151(9) Uani 1 1 d . . . . .
H4 H 0.598119 0.466878 0.581257 0.018 Uiso 1 1 calc R . . . .
C5 C 0.6441(5) 0.6604(4) 0.6235(3) 0.0174(9) Uani 1 1 d . . . . .
H5 H 0.578025 0.663748 0.577650 0.021 Uiso 1 1 calc R . . . .
C11 C 1.1343(5) 0.7384(4) 0.9562(3) 0.0195(10) Uani 1 1 d . . . . .
H11 H 1.198005 0.810345 1.001195 0.023 Uiso 1 1 calc R . . . .
C22 C 1.2414(5) 0.5321(4) 0.6490(3) 0.0208(10) Uani 1 1 d . . . . .
H22 H 1.348862 0.593501 0.673176 0.025 Uiso 1 1 calc R . . . .
C12 C 1.1407(5) 0.6185(4) 0.9514(3) 0.0180(10) Uani 1 1 d . . . . .
H12 H 1.211324 0.610396 0.993166 0.022 Uiso 1 1 calc R . . . .
C9 C 1.0152(5) 0.8723(4) 0.8910(3) 0.0216(10) Uani 1 1 d . . . . .
H9 H 1.072989 0.946622 0.935242 0.026 Uiso 1 1 calc R . . . .
C15 C 1.1845(5) 0.3788(4) 0.9470(3) 0.0187(10) Uani 1 1 d . . . . .
H15A H 1.288877 0.446668 0.947223 0.022 Uiso 1 1 calc R . . . .
H15B H 1.165026 0.402168 0.999204 0.022 Uiso 1 1 calc R . . . .
C33 C 0.1045(5) 0.1402(4) 0.6287(3) 0.0186(10) Uani 1 1 d . . . . .
H33A H 0.142056 0.235126 0.651573 0.022 Uiso 1 1 calc R . . . .
H33B H -0.007527 0.103950 0.597633 0.022 Uiso 1 1 calc R . . . .
C13 C 1.0433(5) 0.5077(4) 0.8852(3) 0.0144(9) Uani 1 1 d . . . . .
C14 C 1.0533(5) 0.3773(4) 0.8799(3) 0.0183(9) Uani 1 1 d . . . . .
H14A H 1.071746 0.350487 0.827963 0.022 Uiso 1 1 calc R . . . .
H14B H 0.949490 0.309767 0.880750 0.022 Uiso 1 1 calc R . . . .
C21 C 1.1297(5) 0.5130(4) 0.6953(3) 0.0165(9) Uani 1 1 d . . . . .
H21 H 1.164744 0.561285 0.749384 0.020 Uiso 1 1 calc R . . . .
C17 C 1.3201(6) 0.2456(5) 1.0034(3) 0.0274(11) Uani 1 1 d . . . . .
H17A H 1.422266 0.318071 1.007238 0.041 Uiso 1 1 calc GR . . . .
H17B H 1.327202 0.162439 0.991176 0.041 Uiso 1 1 calc GR . . . .
H17C H 1.293344 0.257165 1.054179 0.041 Uiso 1 1 calc GR . . . .
C34 C 0.1127(6) 0.0737(5) 0.6975(3) 0.0274(11) Uani 1 1 d . . . . .
H34A H 0.080368 -0.019693 0.675606 0.041 Uiso 1 1 calc GR . . . .
H34B H 0.041399 0.083577 0.728727 0.041 Uiso 1 1 calc GR . . . .
H34C H 0.221500 0.114914 0.731796 0.041 Uiso 1 1 calc GR . . . .
C16 C 1.1885(6) 0.2441(4) 0.9357(3) 0.0243(11) Uani 1 1 d . . . . .
H16A H 1.208369 0.220867 0.883610 0.029 Uiso 1 1 calc R . . . .
H16B H 1.084014 0.176166 0.935317 0.029 Uiso 1 1 calc R . . . .
C36 C 0.5689(6) 0.4088(5) 0.8426(3) 0.0243(11) Uani 1 1 d D . . . .
H36A H 0.671454 0.486264 0.869615 0.029 Uiso 1 1 calc R . . . .
H36B H 0.528299 0.365658 0.883529 0.029 Uiso 1 1 calc R . . . .
C35 C 0.4500(6) 0.4528(5) 0.8009(3) 0.0277(11) Uani 1 1 d . . . . .
H35A H 0.486110 0.488841 0.757525 0.042 Uiso 1 1 calc GR . . . .
H35B H 0.442848 0.520063 0.839374 0.042 Uiso 1 1 calc GR . . . .
H35C H 0.345537 0.377350 0.779150 0.042 Uiso 1 1 calc GR . . . .
C38 C 0.4513(6) 0.0047(5) 0.8340(4) 0.0394(14) Uani 1 1 d . . . . .
H38A H 0.394863 -0.001257 0.779618 0.047 Uiso 1 1 calc R . . . .
H38B H 0.387147 0.015961 0.870140 0.047 Uiso 1 1 calc R . . . .
C37 C 0.4624(8) -0.1216(6) 0.8342(5) 0.061(2) Uani 1 1 d . . . . .
H37A H 0.512651 -0.140037 0.793159 0.092 Uiso 1 1 calc GR . . . .
H37B H 0.355844 -0.193163 0.823240 0.092 Uiso 1 1 calc GR . . . .
H37C H 0.526131 -0.114104 0.886498 0.092 Uiso 1 1 calc GR . . . .
H2 H 0.680(7) 0.091(5) 0.838(3) 0.048(18) 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
Ir1 Cl1 2.5225(10) . ?
Ir1 O1 2.313(3) . ?
Ir1 N1 2.115(3) . ?
Ir1 N2 2.095(3) . ?
Ir1 C20 1.985(4) . ?
Ir1 C3 1.994(4) . ?
O1 C36 1.432(5) . ?
N1 C1 1.380(5) . ?
N1 C13 1.356(5) . ?
N2 C18 1.378(5) . ?
N2 C30 1.353(5) . ?
O2 C38 1.432(6) . ?
C19 C20 1.417(6) . ?
C19 C18 1.420(6) . ?
C19 C24 1.402(6) . ?
C20 C21 1.387(6) . ?
C29 C28 1.365(6) . ?
C29 C30 1.407(6) . ?
C27 C28 1.388(6) . ?
C27 C18 1.399(6) . ?
C27 C26 1.426(6) . ?
C1 C2 1.412(6) . ?
C1 C10 1.408(6) . ?
C7 C2 1.409(6) . ?
C7 C6 1.406(6) . ?
C7 C8 1.423(6) . ?
C2 C3 1.413(5) . ?
C6 C5 1.369(6) . ?
C3 C4 1.382(5) . ?
C24 C25 1.438(6) . ?
C24 C23 1.415(6) . ?
C30 C31 1.489(6) . ?
C25 C26 1.352(6) . ?
C31 C32 1.535(5) . ?
C32 C33 1.528(6) . ?
C23 C22 1.363(6) . ?
C8 C9 1.350(6) . ?
C10 C11 1.393(6) . ?
C10 C9 1.436(6) . ?
C4 C5 1.402(6) . ?
C11 C12 1.369(6) . ?
C22 C21 1.399(6) . ?
C12 C13 1.401(6) . ?
C15 C14 1.524(5) . ?
C15 C16 1.518(6) . ?
C33 C34 1.511(6) . ?
C13 C14 1.501(6) . ?
C17 C16 1.533(6) . ?
C36 C35 1.509(6) . ?
C38 C37 1.471(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ir1 Cl1 82.48(8) . . ?
N1 Ir1 Cl1 106.48(9) . . ?
N1 Ir1 O1 84.96(12) . . ?
N2 Ir1 Cl1 81.45(9) . . ?
N2 Ir1 O1 103.55(12) . . ?
N2 Ir1 N1 169.24(13) . . ?
C20 Ir1 Cl1 94.72(12) . . ?
C20 Ir1 O1 173.93(14) . . ?
C20 Ir1 N1 90.70(16) . . ?
C20 Ir1 N2 81.27(16) . . ?
C20 Ir1 C3 90.49(16) . . ?
C3 Ir1 Cl1 170.67(12) . . ?
C3 Ir1 O1 93.03(14) . . ?
C3 Ir1 N1 81.14(15) . . ?
C3 Ir1 N2 91.72(15) . . ?
C36 O1 Ir1 126.0(3) . . ?
C1 N1 Ir1 111.3(3) . . ?
C13 N1 Ir1 130.4(3) . . ?
C13 N1 C1 118.2(3) . . ?
C18 N2 Ir1 112.0(3) . . ?
C30 N2 Ir1 129.8(3) . . ?
C30 N2 C18 118.2(3) . . ?
C20 C19 C18 116.4(4) . . ?
C24 C19 C20 123.3(4) . . ?
C24 C19 C18 120.3(4) . . ?
C19 C20 Ir1 114.0(3) . . ?
C21 C20 Ir1 129.9(3) . . ?
C21 C20 C19 116.1(4) . . ?
C28 C29 C30 121.2(4) . . ?
C28 C27 C18 117.4(4) . . ?
C28 C27 C26 124.9(4) . . ?
C18 C27 C26 117.8(4) . . ?
N1 C1 C2 116.8(4) . . ?
N1 C1 C10 122.6(4) . . ?
C10 C1 C2 120.6(4) . . ?
C29 C28 C27 119.8(4) . . ?
N2 C18 C19 116.2(4) . . ?
N2 C18 C27 123.2(4) . . ?
C27 C18 C19 120.5(4) . . ?
C2 C7 C8 118.7(4) . . ?
C6 C7 C2 117.6(4) . . ?
C6 C7 C8 123.8(4) . . ?
C1 C2 C3 116.9(4) . . ?
C7 C2 C1 120.0(4) . . ?
C7 C2 C3 123.0(4) . . ?
C5 C6 C7 120.0(4) . . ?
C2 C3 Ir1 113.8(3) . . ?
C4 C3 Ir1 129.4(3) . . ?
C4 C3 C2 116.8(4) . . ?
C19 C24 C25 118.8(4) . . ?
C19 C24 C23 117.8(4) . . ?
C23 C24 C25 123.4(4) . . ?
N2 C30 C29 120.1(4) . . ?
N2 C30 C31 118.1(4) . . ?
C29 C30 C31 121.7(4) . . ?
C26 C25 C24 119.8(4) . . ?
C30 C31 C32 115.9(4) . . ?
C25 C26 C27 122.8(4) . . ?
C33 C32 C31 112.2(3) . . ?
C22 C23 C24 119.4(4) . . ?
C9 C8 C7 121.5(4) . . ?
C1 C10 C9 118.2(4) . . ?
C11 C10 C1 117.9(4) . . ?
C11 C10 C9 124.0(4) . . ?
C3 C4 C5 121.1(4) . . ?
C6 C5 C4 121.5(4) . . ?
C12 C11 C10 119.2(4) . . ?
C23 C22 C21 122.0(4) . . ?
C11 C12 C13 121.5(4) . . ?
C8 C9 C10 121.0(4) . . ?
C16 C15 C14 111.8(3) . . ?
C34 C33 C32 114.0(4) . . ?
N1 C13 C12 120.5(4) . . ?
N1 C13 C14 118.4(4) . . ?
C12 C13 C14 121.1(4) . . ?
C13 C14 C15 115.4(4) . . ?
C20 C21 C22 121.3(4) . . ?
C15 C16 C17 111.8(4) . . ?
O1 C36 C35 110.3(4) . . ?
O2 C38 C37 113.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.106
_oxdiff_exptl_absorpt_empirical_full_min 0.926
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2071813'
loop_
_audit_author_name
_audit_author_address
'Kazuyoshi Takimoto'
;Ehime University
Japan
;
_audit_update_record             
;
2021-03-21 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H32 Cl Ir N2 O'
_chemical_formula_sum            'C35 H32 Cl Ir N2 O'
_chemical_formula_weight         724.27

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'
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'
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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   26.0164(6)
_cell_length_b                   26.0164(6)
_cell_length_c                   23.1213(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     13553.1(7)
_cell_formula_units_Z            18
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29087
_cell_measurement_theta_min      1.57
_cell_measurement_theta_max      31.13

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             6444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    4.552
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.352
_exptl_absorpt_correction_T_max  0.760
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            77910
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.565
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7270
_reflns_number_gt                6174
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.2 (Rigaku, 2019)'
_computing_publication_material  'CrystalStructure 4.3.2 (Rigaku, 2019)'
_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)+(0.0326P)²+242.6022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7270
_refine_ls_number_parameters     417
_refine_ls_number_restraints     202
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.066
_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 0.40304(2) 0.46987(2) 0.31454(2) 0.03374(8) Uani 1 1 d . . . . .
N1 N 0.4901(2) 0.5076(2) 0.3453(2) 0.0398(12) Uani 1 1 d . . . . .
N2 N 0.3163(2) 0.4166(2) 0.2808(2) 0.0369(11) Uani 1 1 d . . . . .
C1 C 0.5187(3) 0.5503(4) 0.3860(3) 0.058(2) Uani 1 1 d . . . . .
C2 C 0.5770(3) 0.5666(4) 0.4022(3) 0.060(2) Uani 1 1 d . . . . .
H2 H 0.595203 0.593918 0.433076 0.072 Uiso 1 1 calc R U . . .
C3 C 0.6077(3) 0.5449(3) 0.3756(3) 0.0514(18) Uani 1 1 d . . . . .
H3 H 0.647209 0.557233 0.387229 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5815(3) 0.5039(3) 0.3306(3) 0.0415(14) Uani 1 1 d . . . . .
C5 C 0.6101(3) 0.4791(3) 0.2982(3) 0.0509(17) Uani 1 1 d . . . . .
H5 H 0.649102 0.488407 0.308924 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5839(3) 0.4428(3) 0.2526(3) 0.0471(16) Uani 1 1 d . . . . .
H6 H 0.604812 0.427516 0.231701 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5249(3) 0.4271(3) 0.2353(2) 0.0374(13) Uani 1 1 d . . . . .
C8 C 0.4963(3) 0.3927(3) 0.1866(2) 0.0370(13) Uani 1 1 d . . . . .
H8 H 0.515949 0.377816 0.163102 0.044 Uiso 1 1 calc R U . . .
C9 C 0.4399(3) 0.3804(3) 0.1725(2) 0.0368(13) Uani 1 1 d . . . . .
H9 H 0.421590 0.358211 0.138547 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4090(3) 0.3999(3) 0.2074(2) 0.0355(13) Uani 1 1 d . . . . .
H10 H 0.369494 0.389586 0.197596 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4355(3) 0.4342(3) 0.2561(2) 0.0327(12) Uani 1 1 d . . . . .
C12 C 0.4940(3) 0.4479(3) 0.2689(2) 0.0326(12) Uani 1 1 d . . . . .
C13 C 0.5221(3) 0.4863(3) 0.3166(2) 0.0340(13) Uani 1 1 d . . . . .
C14 C 0.4909(4) 0.5858(4) 0.4125(3) 0.068(2) Uani 1 1 d . . . . .
H14A H 0.521485 0.628283 0.415138 0.082 Uiso 1 1 calc R U . . .
H14B H 0.458642 0.582223 0.387118 0.082 Uiso 1 1 calc R U . . .
C15 C 0.4674(4) 0.5634(4) 0.4696(4) 0.070(2) Uani 1 1 d . . . . .
H15A H 0.498650 0.564239 0.494668 0.084 Uiso 1 1 calc R U . . .
H15B H 0.434151 0.522000 0.467097 0.084 Uiso 1 1 calc R U . . .
C16 C 0.4450(5) 0.6055(4) 0.4950(4) 0.078(3) Uani 1 1 d . . . . .
H16A H 0.478529 0.646801 0.496307 0.094 Uiso 1 1 calc R U . . .
H16B H 0.414194 0.604561 0.469097 0.094 Uiso 1 1 calc R U . . .
C17 C 0.4186(5) 0.5857(4) 0.5572(4) 0.083(3) Uani 1 1 d . . . . .
H17A H 0.381781 0.547357 0.555054 0.125 Uiso 1 1 calc R U . . .
H17B H 0.410341 0.615441 0.573789 0.125 Uiso 1 1 calc R U . . .
H17C H 0.447332 0.581889 0.581632 0.125 Uiso 1 1 calc R U . . .
C18 C 0.2878(3) 0.4283(3) 0.2385(3) 0.0464(16) Uani 1 1 d . . . . .
C19 C 0.2301(3) 0.3858(3) 0.2223(3) 0.0500(17) Uani 1 1 d . . . . .
H19 H 0.211424 0.394504 0.191603 0.060 Uiso 1 1 calc R U . . .
C20 C 0.2005(3) 0.3329(3) 0.2489(3) 0.0478(16) Uani 1 1 d . . . . .
H20 H 0.161090 0.304872 0.237575 0.057 Uiso 1 1 calc R U . . .
C21 C 0.2285(3) 0.3195(3) 0.2937(3) 0.0442(15) Uani 1 1 d . . . . .
C22 C 0.2014(3) 0.2646(3) 0.3247(4) 0.0549(18) Uani 1 1 d . . . . .
H22 H 0.161995 0.234963 0.315236 0.066 Uiso 1 1 calc R U . . .
C23 C 0.2307(3) 0.2540(3) 0.3672(4) 0.0545(18) Uani 1 1 d . . . . .
H23 H 0.211010 0.217522 0.387856 0.065 Uiso 1 1 calc R U . . .
C24 C 0.2903(3) 0.2964(3) 0.3815(3) 0.0442(15) Uani 1 1 d . . . . .
C25 C 0.3241(3) 0.2872(3) 0.4242(3) 0.0483(17) Uani 1 1 d . . . . .
H25 H 0.307308 0.250671 0.444526 0.058 Uiso 1 1 calc R U . . .
C26 C 0.3806(3) 0.3309(4) 0.4359(3) 0.0494(17) Uani 1 1 d . . . . .
H26 H 0.402591 0.324453 0.464975 0.059 Uiso 1 1 calc R U . . .
C27 C 0.4072(3) 0.3852(3) 0.4062(3) 0.0459(16) Uani 1 1 d . . . . .
H27 H 0.446622 0.414883 0.415452 0.055 Uiso 1 1 calc R U . . .
C28 C 0.3764(3) 0.3958(3) 0.3633(2) 0.0368(13) Uani 1 1 d . . . . .
C29 C 0.3179(3) 0.3509(3) 0.3519(2) 0.0374(14) Uani 1 1 d . . . . .
C30 C 0.2867(3) 0.3623(3) 0.3078(2) 0.0374(13) Uani 1 1 d . . . . .
C31 C 0.3155(3) 0.4867(4) 0.2093(3) 0.065(2) Uani 0.817(9) 1 d D U P A 1
H31A H 0.294583 0.482733 0.172394 0.078 Uiso 0.817(9) 1 calc R U P A 1
H31B H 0.357298 0.499214 0.200173 0.078 Uiso 0.817(9) 1 calc R U P A 1
C32 C 0.3138(5) 0.5362(5) 0.2471(5) 0.074(3) Uani 0.817(9) 1 d D U P A 1
H32A H 0.340191 0.544129 0.280792 0.088 Uiso 0.817(9) 1 calc R U P A 1
H32B H 0.330934 0.573027 0.223808 0.088 Uiso 0.817(9) 1 calc R U P A 1
C33 C 0.2552(5) 0.5241(6) 0.2689(7) 0.103(4) Uani 0.817(9) 1 d D U P A 1
H33A H 0.234296 0.483428 0.285233 0.123 Uiso 0.817(9) 1 calc R U P A 1
H33B H 0.231495 0.524615 0.235658 0.123 Uiso 0.817(9) 1 calc R U P A 1
C34 C 0.2561(5) 0.5679(5) 0.3160(6) 0.099(4) Uani 0.817(9) 1 d D U P A 1
H34A H 0.284680 0.573115 0.346326 0.148 Uiso 0.817(9) 1 calc R U P A 1
H34B H 0.216497 0.551573 0.333032 0.148 Uiso 0.817(9) 1 calc R U P A 1
H34C H 0.267803 0.606326 0.298119 0.148 Uiso 0.817(9) 1 calc R U P A 1
C131 C 0.3155(3) 0.4867(4) 0.2093(3) 0.065(2) Uani 0.183(9) 1 d D U P A 2
H13A H 0.317087 0.481429 0.167106 0.078 Uiso 0.183(9) 1 calc R U P A 2
H13B H 0.356584 0.511926 0.223569 0.078 Uiso 0.183(9) 1 calc R U P A 2
C132 C 0.2792(15) 0.5166(14) 0.2219(18) 0.069(6) Uani 0.183(9) 1 d D U P A 2
H13C H 0.276265 0.522146 0.263874 0.083 Uiso 0.183(9) 1 calc R U P A 2
H13D H 0.238898 0.494432 0.204943 0.083 Uiso 0.183(9) 1 calc R U P A 2
C133 C 0.3191(18) 0.5769(14) 0.1900(18) 0.072(8) Uani 0.183(9) 1 d D U P A 2
H13E H 0.361624 0.592279 0.198505 0.087 Uiso 0.183(9) 1 calc R U P A 2
H13F H 0.312904 0.572357 0.147675 0.087 Uiso 0.183(9) 1 calc R U P A 2
C134 C 0.298(2) 0.6182(16) 0.215(2) 0.083(10) Uani 0.183(9) 1 d D U P A 2
H13G H 0.258829 0.607021 0.199118 0.125 Uiso 0.183(9) 1 calc R U P A 2
H13H H 0.326317 0.659338 0.204500 0.125 Uiso 0.183(9) 1 calc R U P A 2
H13I H 0.295337 0.614350 0.257203 0.125 Uiso 0.183(9) 1 calc R U P A 2
Cl1 Cl 0.4509(2) 0.56287(18) 0.25670(19) 0.0432(14) Uani 0.71(2) 1 d . . P B 3
C35 C 0.3673(7) 0.4995(7) 0.3697(6) 0.040(3) Uani 0.71(2) 1 d . U P B 3
O1 O 0.3418(4) 0.5128(6) 0.3982(5) 0.046(2) Uani 0.71(2) 1 d . U P B 3
Cl11 Cl 0.3447(5) 0.4939(6) 0.3842(3) 0.042(3) Uani 0.29(2) 1 d . . P B 4
C135 C 0.4302(17) 0.5421(18) 0.2719(16) 0.044(7) Uani 0.29(2) 1 d . U P B 4
O101 O 0.4505(17) 0.5837(17) 0.2541(16) 0.061(9) Uani 0.29(2) 1 d . U 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 C135 1.92(5) . ?
Ir1 C35 1.951(17) . ?
Ir1 C28 2.032(6) . ?
Ir1 C11 2.046(6) . ?
Ir1 N1 2.093(5) . ?
Ir1 N2 2.120(5) . ?
Ir1 Cl1 2.486(4) . ?
Ir1 Cl11 2.498(9) . ?
N1 C1 1.358(8) . ?
N1 C13 1.379(8) . ?
N2 C18 1.350(8) . ?
N2 C30 1.376(8) . ?
C1 C2 1.407(10) . ?
C1 C14 1.556(12) . ?
C2 C3 1.335(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(9) . ?
C3 H3 0.9500 . ?
C4 C13 1.413(8) . ?
C4 C5 1.418(10) . ?
C5 C6 1.352(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.435(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(8) . ?
C7 C12 1.405(8) . ?
C8 C9 1.375(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.402(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.410(8) . ?
C12 C13 1.420(8) . ?
C14 C15 1.448(11) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.589(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.566(12) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.398(9) . ?
C18 C131 1.480(10) . ?
C18 C31 1.480(10) . ?
C19 C20 1.344(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.407(10) . ?
C20 H20 0.9500 . ?
C21 C30 1.398(9) . ?
C21 C22 1.428(10) . ?
C22 C23 1.355(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.423(10) . ?
C23 H23 0.9500 . ?
C24 C29 1.406(9) . ?
C24 C25 1.417(9) . ?
C25 C26 1.363(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.403(10) . ?
C26 H26 0.9500 . ?
C27 C28 1.386(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.404(9) . ?
C29 C30 1.424(8) . ?
C31 C32 1.573(12) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.484(13) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.567(14) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C131 C132 1.521(19) . ?
C131 H13A 0.9900 . ?
C131 H13B 0.9900 . ?
C132 C133 1.566(19) . ?
C132 H13C 0.9900 . ?
C132 H13D 0.9900 . ?
C133 C134 1.54(2) . ?
C133 H13E 0.9900 . ?
C133 H13F 0.9900 . ?
C134 C134 1.96(7) 2_665 ?
C134 C134 1.96(7) 3_565 ?
C134 H13G 0.9800 . ?
C134 H13H 0.9800 . ?
C134 H13I 0.9800 . ?
C35 O1 1.10(3) . ?
C135 O101 1.02(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C135 Ir1 C28 177.1(9) . . ?
C35 Ir1 C28 90.5(5) . . ?
C135 Ir1 C11 94.1(11) . . ?
C35 Ir1 C11 176.5(5) . . ?
C28 Ir1 C11 87.6(2) . . ?
C135 Ir1 N1 86.1(10) . . ?
C35 Ir1 N1 102.2(4) . . ?
C28 Ir1 N1 91.9(2) . . ?
C11 Ir1 N1 80.9(2) . . ?
C135 Ir1 N2 101.6(9) . . ?
C35 Ir1 N2 86.4(5) . . ?
C28 Ir1 N2 80.7(2) . . ?
C11 Ir1 N2 90.4(2) . . ?
N1 Ir1 N2 168.8(2) . . ?
C35 Ir1 Cl1 94.2(4) . . ?
C28 Ir1 Cl1 171.4(2) . . ?
C11 Ir1 Cl1 88.1(2) . . ?
N1 Ir1 Cl1 80.08(19) . . ?
N2 Ir1 Cl1 106.83(17) . . ?
C135 Ir1 Cl11 93.4(10) . . ?
C28 Ir1 Cl11 85.3(3) . . ?
C11 Ir1 Cl11 168.5(3) . . ?
N1 Ir1 Cl11 108.3(3) . . ?
N2 Ir1 Cl11 79.6(3) . . ?
C1 N1 C13 117.9(6) . . ?
C1 N1 Ir1 129.8(5) . . ?
C13 N1 Ir1 112.1(4) . . ?
C18 N2 C30 118.2(5) . . ?
C18 N2 Ir1 130.2(4) . . ?
C30 N2 Ir1 111.7(4) . . ?
N1 C1 C2 119.9(7) . . ?
N1 C1 C14 122.1(6) . . ?
C2 C1 C14 117.8(6) . . ?
C3 C2 C1 122.1(7) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.9(7) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C13 117.1(6) . . ?
C3 C4 C5 125.0(6) . . ?
C13 C4 C5 118.0(6) . . ?
C6 C5 C4 122.3(7) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 120.7(6) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C12 117.9(6) . . ?
C8 C7 C6 123.8(6) . . ?
C12 C7 C6 118.3(6) . . ?
C9 C8 C7 120.2(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121.3(5) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 120.5(6) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 117.4(5) . . ?
C10 C11 Ir1 129.9(5) . . ?
C12 C11 Ir1 112.7(4) . . ?
C7 C12 C11 122.6(5) . . ?
C7 C12 C13 120.5(6) . . ?
C11 C12 C13 116.8(5) . . ?
N1 C13 C4 122.7(5) . . ?
N1 C13 C12 117.1(5) . . ?
C4 C13 C12 120.1(6) . . ?
C15 C14 C1 110.4(8) . . ?
C15 C14 H14A 109.6 . . ?
C1 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C1 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 106.6(7) . . ?
C14 C15 H15A 110.4 . . ?
C16 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C17 C16 C15 111.4(8) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 120.6(6) . . ?
N2 C18 C131 121.4(6) . . ?
C19 C18 C131 118.0(6) . . ?
N2 C18 C31 121.4(6) . . ?
C19 C18 C31 118.0(6) . . ?
C20 C19 C18 121.8(6) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 119.2(6) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C30 C21 C20 117.6(6) . . ?
C30 C21 C22 118.4(6) . . ?
C20 C21 C22 124.0(6) . . ?
C23 C22 C21 121.4(7) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C24 121.1(7) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C29 C24 C25 117.5(7) . . ?
C29 C24 C23 118.6(6) . . ?
C25 C24 C23 123.9(7) . . ?
C26 C25 C24 120.0(7) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 121.6(6) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C28 C27 C26 120.5(7) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 117.5(6) . . ?
C27 C28 Ir1 129.0(5) . . ?
C29 C28 Ir1 113.5(4) . . ?
C28 C29 C24 122.8(6) . . ?
C28 C29 C30 117.0(6) . . ?
C24 C29 C30 120.1(6) . . ?
N2 C30 C21 122.6(6) . . ?
N2 C30 C29 117.1(6) . . ?
C21 C30 C29 120.3(6) . . ?
C18 C31 C32 112.9(6) . . ?
C18 C31 H31A 109.0 . . ?
C32 C31 H31A 109.0 . . ?
C18 C31 H31B 109.0 . . ?
C32 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C33 C32 C31 117.5(9) . . ?
C33 C32 H32A 107.9 . . ?
C31 C32 H32A 107.9 . . ?
C33 C32 H32B 107.9 . . ?
C31 C32 H32B 107.9 . . ?
H32A C32 H32B 107.2 . . ?
C32 C33 C34 116.2(10) . . ?
C32 C33 H33A 108.2 . . ?
C34 C33 H33A 108.2 . . ?
C32 C33 H33B 108.2 . . ?
C34 C33 H33B 108.2 . . ?
H33A C33 H33B 107.4 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 C131 C132 109.3(12) . . ?
C18 C131 H13A 109.8 . . ?
C132 C131 H13A 109.8 . . ?
C18 C131 H13B 109.8 . . ?
C132 C131 H13B 109.8 . . ?
H13A C131 H13B 108.3 . . ?
C131 C132 C133 98.7(19) . . ?
C131 C132 H13C 112.0 . . ?
C133 C132 H13C 112.0 . . ?
C131 C132 H13D 112.0 . . ?
C133 C132 H13D 112.0 . . ?
H13C C132 H13D 109.7 . . ?
C134 C133 C132 103(2) . . ?
C134 C133 H13E 111.1 . . ?
C132 C133 H13E 111.1 . . ?
C134 C133 H13F 111.1 . . ?
C132 C133 H13F 111.1 . . ?
H13E C133 H13F 109.0 . . ?
C133 C134 C134 86(4) . 2_665 ?
C133 C134 C134 140(3) . 3_565 ?
C134 C134 C134 59.998(4) 2_665 3_565 ?
C133 C134 H13G 109.5 . . ?
C134 C134 H13G 144.1 2_665 . ?
C134 C134 H13G 90.8 3_565 . ?
C133 C134 H13H 109.5 . . ?
C134 C134 H13H 35.2 2_665 . ?
C134 C134 H13H 30.7 3_565 . ?
H13G C134 H13H 109.5 . . ?
C133 C134 H13I 109.5 . . ?
C134 C134 H13I 94.3 2_665 . ?
C134 C134 H13I 94.6 3_565 . ?
H13G C134 H13I 109.5 . . ?
H13H C134 H13I 109.5 . . ?
O1 C35 Ir1 173.0(12) . . ?
O101 C135 Ir1 170(4) . . ?

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
C13 N1 C1 C2 -7.0(11) . . . . ?
Ir1 N1 C1 C2 176.3(6) . . . . ?
C13 N1 C1 C14 168.3(7) . . . . ?
Ir1 N1 C1 C14 -8.4(11) . . . . ?
N1 C1 C2 C3 5.5(13) . . . . ?
C14 C1 C2 C3 -170.0(8) . . . . ?
C1 C2 C3 C4 -1.0(13) . . . . ?
C2 C3 C4 C13 -1.6(11) . . . . ?
C2 C3 C4 C5 178.1(7) . . . . ?
C3 C4 C5 C6 -175.4(7) . . . . ?
C13 C4 C5 C6 4.4(10) . . . . ?
C4 C5 C6 C7 -0.8(11) . . . . ?
C5 C6 C7 C8 176.0(6) . . . . ?
C5 C6 C7 C12 -3.3(10) . . . . ?
C12 C7 C8 C9 0.3(9) . . . . ?
C6 C7 C8 C9 -179.0(6) . . . . ?
C7 C8 C9 C10 -2.3(9) . . . . ?
C8 C9 C10 C11 2.4(9) . . . . ?
C9 C10 C11 C12 -0.4(9) . . . . ?
C9 C10 C11 Ir1 179.3(4) . . . . ?
C8 C7 C12 C11 1.7(9) . . . . ?
C6 C7 C12 C11 -179.1(6) . . . . ?
C8 C7 C12 C13 -175.7(5) . . . . ?
C6 C7 C12 C13 3.6(9) . . . . ?
C10 C11 C12 C7 -1.6(9) . . . . ?
Ir1 C11 C12 C7 178.6(4) . . . . ?
C10 C11 C12 C13 175.9(5) . . . . ?
Ir1 C11 C12 C13 -3.9(7) . . . . ?
C1 N1 C13 C4 4.5(9) . . . . ?
Ir1 N1 C13 C4 -178.2(5) . . . . ?
C1 N1 C13 C12 -171.6(6) . . . . ?
Ir1 N1 C13 C12 5.7(7) . . . . ?
C3 C4 C13 N1 -0.2(9) . . . . ?
C5 C4 C13 N1 -179.9(6) . . . . ?
C3 C4 C13 C12 175.8(6) . . . . ?
C5 C4 C13 C12 -3.9(9) . . . . ?
C7 C12 C13 N1 176.2(5) . . . . ?
C11 C12 C13 N1 -1.3(8) . . . . ?
C7 C12 C13 C4 0.0(9) . . . . ?
C11 C12 C13 C4 -177.5(5) . . . . ?
N1 C1 C14 C15 102.3(9) . . . . ?
C2 C1 C14 C15 -82.4(10) . . . . ?
C1 C14 C15 C16 175.5(7) . . . . ?
C14 C15 C16 C17 -179.8(8) . . . . ?
C30 N2 C18 C19 -0.9(9) . . . . ?
Ir1 N2 C18 C19 179.0(5) . . . . ?
C30 N2 C18 C131 177.0(6) . . . . ?
Ir1 N2 C18 C131 -3.1(10) . . . . ?
C30 N2 C18 C31 177.0(6) . . . . ?
Ir1 N2 C18 C31 -3.1(10) . . . . ?
N2 C18 C19 C20 1.9(11) . . . . ?
C131 C18 C19 C20 -176.1(7) . . . . ?
C31 C18 C19 C20 -176.1(7) . . . . ?
C18 C19 C20 C21 -1.0(11) . . . . ?
C19 C20 C21 C30 -0.8(10) . . . . ?
C19 C20 C21 C22 -179.5(7) . . . . ?
C30 C21 C22 C23 0.8(11) . . . . ?
C20 C21 C22 C23 179.5(7) . . . . ?
C21 C22 C23 C24 -2.0(11) . . . . ?
C22 C23 C24 C29 2.2(10) . . . . ?
C22 C23 C24 C25 -177.8(7) . . . . ?
C29 C24 C25 C26 1.4(9) . . . . ?
C23 C24 C25 C26 -178.6(6) . . . . ?
C24 C25 C26 C27 -0.9(10) . . . . ?
C25 C26 C27 C28 -0.4(10) . . . . ?
C26 C27 C28 C29 1.1(9) . . . . ?
C26 C27 C28 Ir1 179.0(5) . . . . ?
C27 C28 C29 C24 -0.6(9) . . . . ?
Ir1 C28 C29 C24 -178.8(5) . . . . ?
C27 C28 C29 C30 -180.0(5) . . . . ?
Ir1 C28 C29 C30 1.9(7) . . . . ?
C25 C24 C29 C28 -0.6(9) . . . . ?
C23 C24 C29 C28 179.4(6) . . . . ?
C25 C24 C29 C30 178.7(5) . . . . ?
C23 C24 C29 C30 -1.3(9) . . . . ?
C18 N2 C30 C21 -1.0(9) . . . . ?
Ir1 N2 C30 C21 179.1(5) . . . . ?
C18 N2 C30 C29 179.5(6) . . . . ?
Ir1 N2 C30 C29 -0.4(6) . . . . ?
C20 C21 C30 N2 1.9(9) . . . . ?
C22 C21 C30 N2 -179.3(6) . . . . ?
C20 C21 C30 C29 -178.7(6) . . . . ?
C22 C21 C30 C29 0.1(9) . . . . ?
C28 C29 C30 N2 -1.0(8) . . . . ?
C24 C29 C30 N2 179.7(5) . . . . ?
C28 C29 C30 C21 179.5(5) . . . . ?
C24 C29 C30 C21 0.2(9) . . . . ?
N2 C18 C31 C32 -76.9(9) . . . . ?
C19 C18 C31 C32 101.0(8) . . . . ?
C18 C31 C32 C33 -54.6(12) . . . . ?
C31 C32 C33 C34 168.3(10) . . . . ?
N2 C18 C131 C132 -116.2(19) . . . . ?
C19 C18 C131 C132 62(2) . . . . ?
C18 C131 C132 C133 177(2) . . . . ?
C131 C132 C133 C134 -163(3) . . . . ?
C132 C133 C134 C134 140(3) . . . 2_665 ?
C132 C133 C134 C134 171(4) . . . 3_565 ?

_refine_diff_density_max         3.257
_refine_diff_density_min         -2.189
_refine_diff_density_rms         0.139




