#------------------------------------------------------------------------------
#$Date: 2021-07-09 00:33:40 +0300 (Fri, 09 Jul 2021) $
#$Revision: 267407 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/88/4518875.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4518875
loop_
_publ_author_name
'Alshakova, Iryna D.'
'Albrecht, Martin'
_publ_section_title
;
 Cascade Reductive Friedel--Crafts Alkylation Catalyzed by Robust
 Iridium(III) Hydride Complexes Containing a Protic Triazolylidene Ligand
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              8999
_journal_page_last               9007
_journal_paper_doi               10.1021/acscatal.1c00740
_journal_year                    2021
_chemical_formula_moiety         'C24 H27 Ir N4 O, C4 O'
_chemical_formula_sum            'C28 H27 Ir N4 O2'
_chemical_formula_weight         643.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-31
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                90
_cell_angle_beta                 131.483(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3205(2)
_cell_length_b                   24.9862(2)
_cell_length_c                   15.3632(3)
_cell_measurement_reflns_used    21454
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      77.1080
_cell_measurement_theta_min      3.5390
_cell_volume                     2680.35(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -91.00 -35.00   0.50    0.50    --  -18.75 176.00  88.00  112
  2  ω    -60.00  -1.00   0.50    0.50    --  -18.75 114.00 -49.00  118
  3  ω    -90.00 -39.00   0.50    0.50    --  -18.75-176.00  81.00  102
  4  ω     24.00  91.00   0.50    0.50    --   48.53-114.00-140.00  134
  5  ω     99.00 174.00   0.50    1.25    --  107.16 114.00 -49.00  150
  6  ω     35.00 112.00   0.50    1.25    --  107.16-114.00-140.00  154
  7  ω    -66.00  -9.00   0.50    0.50    --  -18.75 125.00  60.00  114
  8  ω    -25.00  23.00   0.50    0.50    --   48.53 -19.00-120.00   96
  9  ω    -25.00  23.00   0.50    0.50    --   48.53 -19.00 -90.00   96
 10  ω    -25.00  23.00   0.50    0.50    --   48.53 -19.00-150.00   96
 11  ω    -24.00  40.00   0.50    0.50    --   48.53 -38.00-180.00  128
 12  ω    -25.00  23.00   0.50    0.50    --   48.53 -19.00 120.00   96
 13  ω     35.00  62.00   0.50    1.25    --  107.16 -57.00-120.00   54
 14  ω     95.00 174.00   0.50    1.25    --  107.16  19.00 120.00  158
 15  ω     35.00  62.00   0.50    1.25    --  107.16 -57.00 -30.00   54
 16  ω     35.00  62.00   0.50    1.25    --  107.16 -57.00-180.00   54
 17  ω     93.00 174.00   0.50    1.25    --  107.16  57.00 120.00  162
 18  ω     95.00 174.00   0.50    1.25    --  107.16  19.00 -60.00  158
 19  ω     35.00  62.00   0.50    1.25    --  107.16 -57.00 -90.00   54
 20  ω     35.00  62.00   0.50    1.25    --  107.16 -57.00 -60.00   54
 21  ω     35.00  62.00   0.50    1.25    --  107.16 -57.00-150.00   54
 22  ω     35.00 110.00   0.50    1.25    --  107.16 -99.00 -90.00  150
 23  ω     35.00 102.00   0.50    1.25    --  107.16 -77.00 -60.00  134
 24  ω     35.00 117.00   0.50    1.25    --  107.16-125.00 -60.00  164
 25  ω     35.00  62.00   0.50    1.25    --  107.16 -57.00  90.00   54
 26  ω     35.00  62.00   0.50    1.25    --  107.16 -57.00 120.00   54
 27  ω     36.00  62.00   0.50    1.25    --  107.16 -57.00  30.00   52
 28  ω     66.00 101.00   0.50    1.25    --  107.16 -77.00-180.00   70
 29  ω     35.00  62.00   0.50    1.25    --  107.16 -57.00  60.00   54
;
_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      -0.0199411000
_diffrn_orient_matrix_UB_12      0.0050906000
_diffrn_orient_matrix_UB_13      -0.1075670000
_diffrn_orient_matrix_UB_21      -0.0369132000
_diffrn_orient_matrix_UB_22      0.0605163000
_diffrn_orient_matrix_UB_23      -0.0052860000
_diffrn_orient_matrix_UB_31      0.2165320000
_diffrn_orient_matrix_UB_32      0.0106949000
_diffrn_orient_matrix_UB_33      0.0794512000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26394
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.487
_diffrn_reflns_theta_min         3.538
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.885
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (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_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.075
_refine_diff_density_max         1.769
_refine_diff_density_min         -1.562
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0190P)²+8.3782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0660
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5418
_reflns_number_total             5587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c00740_si_005.cif
_cod_data_source_block           19ma116_absorption
_cod_original_cell_volume        2680.35(15)
_cod_database_code               4518875
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C34 H28 Ir1 N4 O2 '
_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.
;
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 Ir1, H
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: O2(0.5) O3(0.5)
 Fixed Uiso: H(0.05)
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
4.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C22(H22A,H22B,H22C), C14(H14A,H14B,H14C)
;
_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 1.762
_oxdiff_exptl_absorpt_empirical_full_min 0.681
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'
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 0.13445(2) 0.73752(2) 0.39032(2) 0.02974(6) Uani 1 1 d . U . . .
N3 N 0.2160(4) 0.59822(12) 0.5575(3) 0.0311(6) Uani 1 1 d . . . . .
N4 N 0.3786(4) 0.69238(12) 0.4584(3) 0.0303(6) Uani 1 1 d . . . . .
O1 O 0.6454(5) 0.42774(12) 0.8563(3) 0.0525(8) Uani 1 1 d . . . . .
N2 N 0.0403(4) 0.60781(14) 0.5212(3) 0.0365(7) Uani 1 1 d . . . . .
N1 N -0.0244(4) 0.65305(13) 0.4608(3) 0.0349(7) Uani 1 1 d . . . . .
C2 C 0.2615(5) 0.63801(14) 0.5194(3) 0.0284(7) Uani 1 1 d . . . . .
C1 C 0.1084(5) 0.67344(15) 0.4583(3) 0.0303(7) Uani 1 1 d . . . . .
C3 C 0.4123(5) 0.64627(15) 0.5183(3) 0.0292(7) Uani 1 1 d . . . . .
C16 C -0.1485(5) 0.77294(16) 0.2729(3) 0.0339(8) Uani 1 1 d . . . . .
C6 C 0.6583(5) 0.67374(17) 0.4857(3) 0.0371(8) Uani 1 1 d . . . . .
H6 H 0.738639 0.683420 0.472342 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3267(5) 0.55379(15) 0.6324(3) 0.0312(7) Uani 1 1 d . . . . .
C15 C -0.0114(6) 0.81459(16) 0.3123(3) 0.0375(8) Uani 1 1 d . . . . .
C7 C 0.5025(5) 0.70516(16) 0.4447(3) 0.0337(8) Uani 1 1 d . . . . .
H7 H 0.482525 0.736668 0.405703 0.040 Uiso 1 1 calc R . . . .
C4 C 0.5697(5) 0.61392(16) 0.5638(3) 0.0340(8) Uani 1 1 d . . . . .
H4 H 0.591747 0.583212 0.605333 0.041 Uiso 1 1 calc R . . . .
C17 C -0.1392(5) 0.73621(16) 0.2048(3) 0.0359(8) Uani 1 1 d . . . . .
C5 C 0.6926(5) 0.62777(17) 0.5467(3) 0.0356(8) Uani 1 1 d . . . . .
H5 H 0.797703 0.606335 0.576060 0.043 Uiso 1 1 calc R . . . .
C9 C 0.2665(5) 0.50249(16) 0.5913(3) 0.0353(8) Uani 1 1 d . . . . .
H9 H 0.155862 0.496830 0.514452 0.042 Uiso 1 1 calc R . . . .
C10 C 0.3697(5) 0.45900(16) 0.6641(4) 0.0366(8) Uani 1 1 d . . . . .
H10 H 0.328453 0.424279 0.636343 0.044 Uiso 1 1 calc R . . . .
C11 C 0.5341(6) 0.46786(16) 0.7777(3) 0.0375(8) Uani 1 1 d . . . . .
C19 C 0.0898(6) 0.80281(17) 0.2739(4) 0.0393(9) Uani 1 1 d . . . . .
C18 C 0.0091(6) 0.75392(18) 0.2069(3) 0.0386(9) Uani 1 1 d . . . . .
C12 C 0.5950(7) 0.51989(18) 0.8184(4) 0.0488(11) Uani 1 1 d . . . . .
H12 H 0.706885 0.525651 0.894882 0.059 Uiso 1 1 calc R . . . .
C20 C 0.0114(7) 0.86420(19) 0.3752(4) 0.0539(12) Uani 1 1 d . . . . .
H20A H -0.015476 0.856130 0.424235 0.081 Uiso 1 1 calc GR . . . .
H20B H -0.075980 0.891118 0.319808 0.081 Uiso 1 1 calc GR . . . .
H20C H 0.140369 0.877157 0.421856 0.081 Uiso 1 1 calc GR . . . .
C13 C 0.4916(6) 0.56291(17) 0.7468(4) 0.0421(9) Uani 1 1 d . . . . .
H13 H 0.531670 0.597664 0.774671 0.051 Uiso 1 1 calc R . . . .
C21 C -0.2958(6) 0.7712(2) 0.2848(4) 0.0478(11) Uani 1 1 d . . . . .
H21A H -0.311723 0.734968 0.297799 0.072 Uiso 1 1 calc GR . . . .
H21B H -0.415554 0.784481 0.214832 0.072 Uiso 1 1 calc GR . . . .
H21C H -0.254246 0.793060 0.349246 0.072 Uiso 1 1 calc GR . . . .
C23 C 0.0659(7) 0.7284(2) 0.1457(4) 0.0538(12) Uani 1 1 d . . . . .
H23A H 0.203034 0.726947 0.197106 0.081 Uiso 1 1 calc GR . . . .
H23B H 0.016550 0.749140 0.078278 0.081 Uiso 1 1 calc GR . . . .
H23C H 0.014653 0.692819 0.122475 0.081 Uiso 1 1 calc GR . . . .
C24 C 0.2332(7) 0.8379(2) 0.2877(5) 0.0572(13) Uani 1 1 d . . . . .
H24A H 0.313726 0.854256 0.363158 0.086 Uiso 1 1 calc GR . . . .
H24B H 0.167980 0.865157 0.229022 0.086 Uiso 1 1 calc GR . . . .
H24C H 0.310244 0.816770 0.279947 0.086 Uiso 1 1 calc GR . . . .
C22 C -0.2701(6) 0.68914(19) 0.1400(4) 0.0508(11) Uani 1 1 d . . . . .
H22A H -0.234268 0.670039 0.102734 0.076 Uiso 1 1 calc GR . . . .
H22B H -0.399776 0.701492 0.082452 0.076 Uiso 1 1 calc GR . . . .
H22C H -0.260150 0.665788 0.193458 0.076 Uiso 1 1 calc GR . . . .
C14 C 0.5944(8) 0.37409(18) 0.8121(4) 0.0597(13) Uani 1 1 d . . . . .
H14A H 0.609773 0.369536 0.756603 0.090 Uiso 1 1 calc GR . . . .
H14B H 0.463402 0.367515 0.775087 0.090 Uiso 1 1 calc GR . . . .
H14C H 0.675879 0.349311 0.874971 0.090 Uiso 1 1 calc GR . . . .
C27 C 0.8368(15) 0.4747(3) 0.6945(9) 0.116(3) Uani 1 1 d . . . . .
C28 C 0.9532(14) 0.4321(3) 0.7748(10) 0.116(3) Uani 1 1 d . . . . .
C26 C 1.1210(15) 0.5037(4) 0.7787(11) 0.136(4) Uani 1 1 d . . . . .
H H 0.280(7) 0.7619(18) 0.549(4) 0.050 Uiso 1 1 d . U . . .
O2 O 1.170(2) 0.4538(5) 0.8159(18) 0.169(7) Uani 0.5 1 d . . P A 1
C25 C 0.9269(11) 0.5184(3) 0.7044(6) 0.0848(19) Uani 1 1 d . . . . .
O3 O 1.143(3) 0.4401(6) 0.8919(12) 0.166(7) Uani 0.5 1 d . . P A 2
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'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -8 -7 0.0471
-6 3 6 0.0329
5 -6 -8 0.0599
-3 -6 -3 0.0516
-6 -1 9 0.0343
0 -5 -1 0.0488
-5 3 2 0.0339
0 5 1 0.0429
4 4 1 0.0345
1 5 -3 0.0373
-1 -5 3 0.0434
1 3 -6 0.0374
3 -3 2 0.0310
-2 5 -1 0.0372
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
N4 Ir1 C16 162.99(14) . . ?
N4 Ir1 C15 144.90(14) . . ?
O2a C26 C25 119.1(11) . . ?
N4 Ir1 C17 124.96(13) . . ?
N4 Ir1 C19 110.80(13) . . ?
N4 Ir1 C18 102.32(13) . . ?
N4 Ir1 H 85.3(14) . . ?
C1 Ir1 N4 77.15(13) . . ?
C1 Ir1 C16 104.98(14) . . ?
C1 Ir1 C15 137.40(15) . . ?
C1 Ir1 C17 102.84(15) . . ?
C1 Ir1 C19 165.60(15) . . ?
C1 Ir1 C18 130.61(16) . . ?
C1 Ir1 H 79.8(14) . . ?
C16 Ir1 C15 38.37(15) . . ?
C16 Ir1 C17 38.05(15) . . ?
C16 Ir1 C19 63.83(14) . . ?
C16 Ir1 C18 63.18(14) . . ?
C16 Ir1 H 111.7(14) . . ?
C15 Ir1 C17 63.03(15) . . ?
C15 Ir1 C19 37.67(15) . . ?
C15 Ir1 C18 62.56(15) . . ?
C15 Ir1 H 94.3(14) . . ?
C17 Ir1 C19 62.77(15) . . ?
C17 Ir1 C18 37.11(15) . . ?
C17 Ir1 H 149.6(14) . . ?
C19 Ir1 C18 37.42(16) . . ?
C19 Ir1 H 112.2(14) . . ?
C18 Ir1 H 149.5(14) . . ?
N2 N3 C8 119.9(3) . . ?
C2 N3 N2 109.3(3) . . ?
C2 N3 C8 130.6(3) . . ?
C3 N4 Ir1 118.4(2) . . ?
C7 N4 Ir1 123.8(3) . . ?
C7 N4 C3 117.7(3) . . ?
C11 O1 C14 116.5(3) . . ?
N1 N2 N3 107.7(3) . . ?
N2 N1 C1 109.7(3) . . ?
N3 C2 C1 106.5(3) . . ?
N3 C2 C3 134.5(3) . . ?
C1 C2 C3 118.6(3) . . ?
N1 C1 Ir1 137.4(3) . . ?
N1 C1 C2 106.8(3) . . ?
C2 C1 Ir1 115.8(2) . . ?
N4 C3 C2 109.7(3) . . ?
N4 C3 C4 121.4(3) . . ?
C4 C3 C2 128.9(3) . . ?
C15 C16 Ir1 72.1(2) . . ?
C15 C16 C17 107.7(3) . . ?
C15 C16 C21 126.9(4) . . ?
C17 C16 Ir1 73.6(2) . . ?
C17 C16 C21 124.9(4) . . ?
C21 C16 Ir1 126.4(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 118.9(3) . . ?
C9 C8 N3 119.8(3) . . ?
C9 C8 C13 120.5(4) . . ?
C13 C8 N3 119.7(3) . . ?
C16 C15 Ir1 69.6(2) . . ?
C16 C15 C19 108.8(4) . . ?
C16 C15 C20 125.4(4) . . ?
C19 C15 Ir1 73.0(2) . . ?
C19 C15 C20 125.7(4) . . ?
C20 C15 Ir1 126.9(3) . . ?
N4 C7 C6 123.1(4) . . ?
N4 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C16 C17 Ir1 68.3(2) . . ?
C16 C17 C22 124.6(4) . . ?
C18 C17 Ir1 72.4(2) . . ?
C18 C17 C16 108.0(4) . . ?
C18 C17 C22 127.3(4) . . ?
C22 C17 Ir1 126.6(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.3 . . ?
O1 C11 C10 123.7(4) . . ?
O1 C11 C12 116.3(4) . . ?
C10 C11 C12 120.0(4) . . ?
C15 C19 Ir1 69.3(2) . . ?
C15 C19 C18 107.0(3) . . ?
C15 C19 C24 126.3(4) . . ?
C18 C19 Ir1 71.8(2) . . ?
C18 C19 C24 126.4(4) . . ?
C24 C19 Ir1 129.6(3) . . ?
C17 C18 Ir1 70.5(2) . . ?
C17 C18 C19 108.4(4) . . ?
C17 C18 C23 126.4(4) . . ?
C19 C18 Ir1 70.8(2) . . ?
C19 C18 C23 125.0(4) . . ?
C23 C18 Ir1 127.0(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 C13 H13 120.4 . . ?
C12 C13 C8 119.1(4) . . ?
C12 C13 H13 120.4 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C26 O2a C28 98.8(9) . . ?
C25 C27 C28 116.9(9) . . ?
C27 C28 O2 96.5(7) . . ?
C27 C28 O3 123.9(10) . . ?
C27 C25 C26 104.8(8) . . ?
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 N4 2.095(3) . ?
Ir1 C1 2.013(4) . ?
Ir1 C16 2.166(3) . ?
Ir1 C15 2.199(4) . ?
Ir1 C17 2.236(4) . ?
Ir1 C19 2.247(4) . ?
Ir1 C18 2.261(4) . ?
Ir1 H 1.94(5) . ?
N3 N2 1.357(4) . ?
N3 C2 1.356(5) . ?
N3 C8 1.431(5) . ?
N4 C3 1.375(5) . ?
N4 C7 1.342(4) . ?
O1 C11 1.371(5) . ?
O1 C14 1.434(6) . ?
N2 N1 1.327(4) . ?
N1 C1 1.362(4) . ?
C2 C1 1.388(5) . ?
C2 C3 1.432(5) . ?
C3 C4 1.391(5) . ?
C16 C15 1.435(6) . ?
C16 C17 1.436(6) . ?
C16 C21 1.500(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(5) . ?
C6 C5 1.380(6) . ?
C8 C9 1.374(5) . ?
C8 C13 1.387(6) . ?
C15 C19 1.436(6) . ?
C15 C20 1.498(6) . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.378(5) . ?
C17 C18 1.431(6) . ?
C17 C22 1.502(6) . ?
C5 H5 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.389(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(6) . ?
C11 C12 1.390(6) . ?
C19 C18 1.446(6) . ?
C19 C24 1.490(6) . ?
C18 C23 1.492(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C13 H13 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C27 C28 1.436(12) . ?
C27 C25 1.323(11) . ?
C28 O2 1.754(15) . ?
C28 O3 1.480(17) . ?
C26 O2 1.323(13) . ?
C26 C25 1.405(11) . ?
