#------------------------------------------------------------------------------
#$Date: 2021-09-27 11:51:07 +0300 (Mon, 27 Sep 2021) $
#$Revision: 269318 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564725.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_1564725
loop_
_publ_author_name
'Medrano-Castillo, Layla J.'
'Collazo-Flores, Miguel Á.'
'Camarena-Díaz, Juan P.'
'Correa-Ayala, Erick'
'Chávez, Daniel'
'Grotjahn, Douglas B.'
'Rheingold, Arnold L.'
'Miranda-Soto, Valentín'
'Parra-Hake, Miguel'
_publ_section_title
;
 Base-free transfer hydrogenation of aryl-ketones, alkyl-ketones and
 alkenones catalyzed by an IrIIICp* complex bearing a triazenide ligand
 functionalized with pyrazole
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119551
_journal_paper_doi               10.1016/j.ica.2020.119551
_journal_volume                  507
_journal_year                    2020
_chemical_formula_moiety         'C21 H27 Cl Ir N5'
_chemical_formula_sum            'C21 H27 Cl Ir N5'
_chemical_formula_weight         577.13
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 118.671(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.5347(13)
_cell_length_b                   7.4472(5)
_cell_length_c                   17.8595(12)
_cell_measurement_reflns_used    3806
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.50
_cell_volume                     2162.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15651
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    6.313
_exptl_absorpt_correction_T_max  0.7863
_exptl_absorpt_correction_T_min  0.5709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.525
_refine_diff_density_min         -1.044
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0251P)²+1.5489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                3540
_reflns_number_total             4461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2020-507-119551.cif
_cod_data_source_block           grot422
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8369 2020-08-20 11:38:08Z andrius 
;
_cod_original_sg_symbol_Hall     ' -P 2ybc '
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1564725
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.285654(12) 0.42107(3) 0.410049(12) 0.01425(7) Uani 1 1 d . . .
Cl1 Cl 0.34563(7) 0.70688(16) 0.46538(7) 0.0179(3) Uani 1 1 d . . .
N1 N 0.3607(3) 0.6110(6) 0.1841(3) 0.0216(10) Uani 1 1 d . . .
N2 N 0.3536(3) 0.5452(6) 0.2521(3) 0.0223(10) Uani 1 1 d . . .
N3 N 0.2485(2) 0.5383(5) 0.2901(2) 0.0166(10) Uani 1 1 d . . .
N4 N 0.1805(2) 0.6170(5) 0.2789(2) 0.0146(9) Uani 1 1 d . . .
N5 N 0.1744(2) 0.5601(6) 0.3457(2) 0.0151(9) Uani 1 1 d . . .
C1 C 0.4368(3) 0.5960(8) 0.1822(4) 0.0301(13) Uani 1 1 d . . .
H1A H 0.4271 0.6162 0.1238 0.045 Uiso 1 1 calc R . .
H1B H 0.4597 0.4756 0.2010 0.045 Uiso 1 1 calc R . .
H1C H 0.4756 0.6859 0.2203 0.045 Uiso 1 1 calc R . .
C2 C 0.2915(3) 0.6891(7) 0.1264(3) 0.0246(13) Uani 1 1 d . . .
H2A H 0.2828 0.7436 0.0746 0.030 Uiso 1 1 calc R . .
C3 C 0.2354(3) 0.6768(8) 0.1553(3) 0.0258(13) Uani 1 1 d . . .
H3A H 0.1803 0.7194 0.1282 0.031 Uiso 1 1 calc R . .
C4 C 0.2769(3) 0.5877(7) 0.2333(3) 0.0188(11) Uani 1 1 d . . .
C5 C 0.1103(3) 0.6274(6) 0.3580(3) 0.0176(11) Uani 1 1 d . . .
C6 C 0.0424(3) 0.7177(7) 0.2962(3) 0.0231(12) Uani 1 1 d . . .
H6 H 0.0370 0.7384 0.2413 0.028 Uiso 1 1 calc R . .
C7 C -0.0164(3) 0.7765(8) 0.3156(3) 0.0252(13) Uani 1 1 d . . .
H7 H -0.0619 0.8423 0.2738 0.030 Uiso 1 1 calc R . .
C8 C -0.0123(3) 0.7439(8) 0.3935(4) 0.0294(13) Uani 1 1 d . . .
C9 C 0.0544(3) 0.6556(8) 0.4542(4) 0.0308(14) Uani 1 1 d . . .
H9 H 0.0589 0.6338 0.5087 0.037 Uiso 1 1 calc R . .
C10 C 0.1147(3) 0.5984(8) 0.4369(3) 0.0227(12) Uani 1 1 d . . .
H10 H 0.1609 0.5371 0.4800 0.027 Uiso 1 1 calc R . .
C11 C -0.0795(4) 0.8086(10) 0.4128(4) 0.0459(18) Uani 1 1 d . . .
H11A H -0.1289 0.7348 0.3814 0.069 Uiso 1 1 calc R . .
H11B H -0.0926 0.9343 0.3953 0.069 Uiso 1 1 calc R . .
H11C H -0.0605 0.7982 0.4742 0.069 Uiso 1 1 calc R . .
C12 C 0.3854(3) 0.2688(7) 0.5101(3) 0.0229(12) Uani 1 1 d . . .
C13 C 0.3119(3) 0.2580(7) 0.5187(3) 0.0195(11) Uani 1 1 d U . .
C14 C 0.2496(3) 0.1727(7) 0.4425(3) 0.0195(12) Uani 1 1 d . . .
C15 C 0.2833(3) 0.1390(7) 0.3872(3) 0.0198(12) Uani 1 1 d . . .
C16 C 0.3680(3) 0.1977(7) 0.4304(3) 0.0216(12) Uani 1 1 d . . .
C17 C 0.4665(3) 0.3443(8) 0.5766(3) 0.0256(13) Uani 1 1 d . . .
H17A H 0.4964 0.2524 0.6198 0.038 Uiso 1 1 calc R . .
H17B H 0.4565 0.4487 0.6039 0.038 Uiso 1 1 calc R . .
H17C H 0.4992 0.3810 0.5495 0.038 Uiso 1 1 calc R . .
C18 C 0.3051(4) 0.3096(8) 0.5968(3) 0.0281(14) Uani 1 1 d . . .
H18A H 0.2475 0.3359 0.5802 0.042 Uiso 1 1 calc R . .
H18B H 0.3387 0.4164 0.6231 0.042 Uiso 1 1 calc R . .
H18C H 0.3245 0.2102 0.6377 0.042 Uiso 1 1 calc R . .
C19 C 0.1645(3) 0.1220(7) 0.4262(4) 0.0269(13) Uani 1 1 d . . .
H19A H 0.1271 0.1194 0.3645 0.040 Uiso 1 1 calc R . .
H19B H 0.1450 0.2106 0.4530 0.040 Uiso 1 1 calc R . .
H19C H 0.1661 0.0030 0.4504 0.040 Uiso 1 1 calc R . .
C20 C 0.2424(4) 0.0504(7) 0.3016(3) 0.0296(14) Uani 1 1 d . . .
H20A H 0.2633 -0.0723 0.3066 0.044 Uiso 1 1 calc R . .
H20B H 0.2542 0.1185 0.2618 0.044 Uiso 1 1 calc R . .
H20C H 0.1828 0.0469 0.2803 0.044 Uiso 1 1 calc R . .
C21 C 0.4261(3) 0.1737(8) 0.3947(4) 0.0303(14) Uani 1 1 d . . .
H21A H 0.4765 0.2425 0.4290 0.045 Uiso 1 1 calc R . .
H21B H 0.4000 0.2168 0.3356 0.045 Uiso 1 1 calc R . .
H21C H 0.4398 0.0462 0.3961 0.045 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
N5 Ir1 N3 58.61(16) . .
N5 Ir1 C15 117.21(18) . .
N3 Ir1 C15 104.34(18) . .
N5 Ir1 C13 121.02(18) . .
N3 Ir1 C13 169.26(18) . .
C15 Ir1 C13 65.8(2) . .
N5 Ir1 C14 102.90(18) . .
N3 Ir1 C14 130.09(18) . .
C15 Ir1 C14 38.8(2) . .
C13 Ir1 C14 39.42(19) . .
N5 Ir1 C16 154.39(18) . .
N3 Ir1 C16 110.49(18) . .
C15 Ir1 C16 39.25(19) . .
C13 Ir1 C16 64.9(2) . .
C14 Ir1 C16 65.0(2) . .
N5 Ir1 C12 159.34(18) . .
N3 Ir1 C12 142.05(19) . .
C15 Ir1 C12 64.9(2) . .
C13 Ir1 C12 39.13(19) . .
C14 Ir1 C12 65.13(19) . .
C16 Ir1 C12 37.7(2) . .
N5 Ir1 Cl1 85.79(12) . .
N3 Ir1 Cl1 84.89(11) . .
C15 Ir1 Cl1 156.85(14) . .
C13 Ir1 Cl1 105.85(14) . .
C14 Ir1 Cl1 143.47(14) . .
C16 Ir1 Cl1 117.70(15) . .
C12 Ir1 Cl1 94.66(15) . .
C2 N1 N2 112.1(4) . .
C2 N1 C1 127.5(5) . .
N2 N1 C1 120.4(4) . .
C4 N2 N1 103.6(4) . .
N4 N3 C4 116.1(4) . .
N4 N3 Ir1 99.3(3) . .
C4 N3 Ir1 142.8(3) . .
N3 N4 N5 102.2(4) . .
N4 N5 C5 118.3(4) . .
N4 N5 Ir1 99.6(3) . .
C5 N5 Ir1 141.1(3) . .
N1 C1 H1A 109.5 . .
N1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
N1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C3 107.6(5) . .
N1 C2 H2A 126.2 . .
C3 C2 H2A 126.2 . .
C2 C3 C4 104.7(5) . .
C2 C3 H3A 127.7 . .
C4 C3 H3A 127.7 . .
N2 C4 C3 112.0(5) . .
N2 C4 N3 118.9(4) . .
C3 C4 N3 129.1(5) . .
C6 C5 C10 118.2(5) . .
C6 C5 N5 124.3(5) . .
C10 C5 N5 117.5(4) . .
C7 C6 C5 119.0(5) . .
C7 C6 H6 120.5 . .
C5 C6 H6 120.5 . .
C6 C7 C8 122.3(5) . .
C6 C7 H7 118.8 . .
C8 C7 H7 118.8 . .
C9 C8 C7 118.7(6) . .
C9 C8 C11 120.1(5) . .
C7 C8 C11 121.2(5) . .
C8 C9 C10 120.0(6) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C9 C10 C5 121.8(5) . .
C9 C10 H10 119.1 . .
C5 C10 H10 119.1 . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C16 C12 C13 108.4(5) . .
C16 C12 C17 126.7(5) . .
C13 C12 C17 124.9(5) . .
C16 C12 Ir1 70.8(3) . .
C13 C12 Ir1 69.1(3) . .
C17 C12 Ir1 125.9(4) . .
C14 C13 C12 107.1(4) . .
C14 C13 C18 126.8(5) . .
C12 C13 C18 125.8(5) . .
C14 C13 Ir1 70.4(3) . .
C12 C13 Ir1 71.8(3) . .
C18 C13 Ir1 127.6(4) . .
C15 C14 C13 108.3(5) . .
C15 C14 C19 126.1(5) . .
C13 C14 C19 125.6(5) . .
C15 C14 Ir1 70.5(3) . .
C13 C14 Ir1 70.2(3) . .
C19 C14 Ir1 126.7(4) . .
C14 C15 C16 107.6(5) . .
C14 C15 C20 127.8(5) . .
C16 C15 C20 124.5(5) . .
C14 C15 Ir1 70.7(3) . .
C16 C15 Ir1 71.5(3) . .
C20 C15 Ir1 125.7(4) . .
C12 C16 C15 108.5(5) . .
C12 C16 C21 127.7(5) . .
C15 C16 C21 123.6(5) . .
C12 C16 Ir1 71.4(3) . .
C15 C16 Ir1 69.2(3) . .
C21 C16 Ir1 127.6(4) . .
C12 C17 H17A 109.5 . .
C12 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C12 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C13 C18 H18A 109.5 . .
C13 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C13 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C14 C19 H19A 109.5 . .
C14 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C14 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C15 C20 H20A 109.5 . .
C15 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C15 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C16 C21 H21A 109.5 . .
C16 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C16 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 N5 2.091(4) .
Ir1 N3 2.100(4) .
Ir1 C15 2.136(5) .
Ir1 C13 2.138(5) .
Ir1 C14 2.140(5) .
Ir1 C16 2.167(5) .
Ir1 C12 2.175(5) .
Ir1 Cl1 2.3850(12) .
N1 C2 1.332(7) .
N1 N2 1.373(6) .
N1 C1 1.432(7) .
N2 C4 1.333(6) .
N3 N4 1.316(6) .
N3 C4 1.397(6) .
N4 N5 1.320(5) .
N5 C5 1.401(6) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.369(7) .
C2 H2A 0.9500 .
C3 C4 1.394(7) .
C3 H3A 0.9500 .
C5 C6 1.385(7) .
C5 C10 1.389(7) .
C6 C7 1.365(7) .
C6 H6 0.9500 .
C7 C8 1.378(8) .
C7 H7 0.9500 .
C8 C9 1.360(8) .
C8 C11 1.522(8) .
C9 C10 1.363(7) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C16 1.404(8) .
C12 C13 1.444(7) .
C12 C17 1.507(7) .
C13 C14 1.443(7) .
C13 C18 1.509(7) .
C14 C15 1.421(7) .
C14 C19 1.508(7) .
C15 C16 1.446(7) .
C15 C20 1.495(7) .
C16 C21 1.504(7) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
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
C2 N1 N2 C4 -0.3(6) . . . .
C1 N1 N2 C4 178.0(5) . . . .
N5 Ir1 N3 N4 3.9(3) . . . .
C15 Ir1 N3 N4 117.3(3) . . . .
C13 Ir1 N3 N4 95.2(10) . . . .
C14 Ir1 N3 N4 84.0(3) . . . .
C16 Ir1 N3 N4 158.0(3) . . . .
C12 Ir1 N3 N4 -175.3(3) . . . .
Cl1 Ir1 N3 N4 -84.3(3) . . . .
N5 Ir1 N3 C4 166.1(6) . . . .
C15 Ir1 N3 C4 -80.5(6) . . . .
C13 Ir1 N3 C4 -102.6(10) . . . .
C14 Ir1 N3 C4 -113.8(6) . . . .
C16 Ir1 N3 C4 -39.8(6) . . . .
C12 Ir1 N3 C4 -13.1(7) . . . .
Cl1 Ir1 N3 C4 77.9(5) . . . .
C4 N3 N4 N5 -173.5(4) . . . .
Ir1 N3 N4 N5 -5.4(3) . . . .
N3 N4 N5 C5 176.0(4) . . . .
N3 N4 N5 Ir1 5.4(4) . . . .
N3 Ir1 N5 N4 -3.9(3) . . . .
C15 Ir1 N5 N4 -94.6(3) . . . .
C13 Ir1 N5 N4 -171.3(3) . . . .
C14 Ir1 N5 N4 -133.2(3) . . . .
C16 Ir1 N5 N4 -74.9(5) . . . .
C12 Ir1 N5 N4 174.8(4) . . . .
Cl1 Ir1 N5 N4 82.7(3) . . . .
N3 Ir1 N5 C5 -170.6(6) . . . .
C15 Ir1 N5 C5 98.7(5) . . . .
C13 Ir1 N5 C5 22.0(6) . . . .
C14 Ir1 N5 C5 60.0(5) . . . .
C16 Ir1 N5 C5 118.3(6) . . . .
C12 Ir1 N5 C5 8.0(9) . . . .
Cl1 Ir1 N5 C5 -84.0(5) . . . .
N2 N1 C2 C3 -0.1(6) . . . .
C1 N1 C2 C3 -178.2(5) . . . .
N1 C2 C3 C4 0.3(6) . . . .
N1 N2 C4 C3 0.5(6) . . . .
N1 N2 C4 N3 179.6(4) . . . .
C2 C3 C4 N2 -0.5(6) . . . .
C2 C3 C4 N3 -179.5(5) . . . .
N4 N3 C4 N2 165.2(4) . . . .
Ir1 N3 C4 N2 4.8(8) . . . .
N4 N3 C4 C3 -15.9(8) . . . .
Ir1 N3 C4 C3 -176.3(4) . . . .
N4 N5 C5 C6 15.0(7) . . . .
Ir1 N5 C5 C6 -179.9(4) . . . .
N4 N5 C5 C10 -166.2(4) . . . .
Ir1 N5 C5 C10 -1.1(8) . . . .
C10 C5 C6 C7 0.9(8) . . . .
N5 C5 C6 C7 179.7(5) . . . .
C5 C6 C7 C8 -2.3(9) . . . .
C6 C7 C8 C9 2.4(9) . . . .
C6 C7 C8 C11 -179.0(6) . . . .
C7 C8 C9 C10 -1.2(9) . . . .
C11 C8 C9 C10 -179.8(6) . . . .
C8 C9 C10 C5 -0.1(9) . . . .
C6 C5 C10 C9 0.3(8) . . . .
N5 C5 C10 C9 -178.6(5) . . . .
N5 Ir1 C12 C16 138.5(5) . . . .
N3 Ir1 C12 C16 -43.4(4) . . . .
C15 Ir1 C12 C16 37.6(3) . . . .
C13 Ir1 C12 C16 119.4(4) . . . .
C14 Ir1 C12 C16 80.7(3) . . . .
Cl1 Ir1 C12 C16 -131.0(3) . . . .
N5 Ir1 C12 C13 19.1(7) . . . .
N3 Ir1 C12 C13 -162.8(3) . . . .
C15 Ir1 C12 C13 -81.8(3) . . . .
C14 Ir1 C12 C13 -38.8(3) . . . .
C16 Ir1 C12 C13 -119.4(4) . . . .
Cl1 Ir1 C12 C13 109.5(3) . . . .
N5 Ir1 C12 C17 -99.5(6) . . . .
N3 Ir1 C12 C17 78.6(6) . . . .
C15 Ir1 C12 C17 159.6(5) . . . .
C13 Ir1 C12 C17 -118.6(6) . . . .
C14 Ir1 C12 C17 -157.4(5) . . . .
C16 Ir1 C12 C17 122.0(6) . . . .
Cl1 Ir1 C12 C17 -9.1(5) . . . .
C16 C12 C13 C14 1.8(6) . . . .
C17 C12 C13 C14 -178.2(5) . . . .
Ir1 C12 C13 C14 61.9(3) . . . .
C16 C12 C13 C18 176.2(5) . . . .
C17 C12 C13 C18 -3.8(8) . . . .
Ir1 C12 C13 C18 -123.7(5) . . . .
C16 C12 C13 Ir1 -60.1(4) . . . .
C17 C12 C13 Ir1 119.9(5) . . . .
N5 Ir1 C13 C14 71.3(3) . . . .
N3 Ir1 C13 C14 -13.5(11) . . . .
C15 Ir1 C13 C14 -37.1(3) . . . .
C16 Ir1 C13 C14 -80.4(3) . . . .
C12 Ir1 C13 C14 -116.5(4) . . . .
Cl1 Ir1 C13 C14 165.9(3) . . . .
N5 Ir1 C13 C12 -172.3(3) . . . .
N3 Ir1 C13 C12 102.9(10) . . . .
C15 Ir1 C13 C12 79.4(3) . . . .
C14 Ir1 C13 C12 116.5(4) . . . .
C16 Ir1 C13 C12 36.0(3) . . . .
Cl1 Ir1 C13 C12 -77.6(3) . . . .
N5 Ir1 C13 C18 -50.7(5) . . . .
N3 Ir1 C13 C18 -135.4(9) . . . .
C15 Ir1 C13 C18 -159.0(5) . . . .
C14 Ir1 C13 C18 -121.9(6) . . . .
C16 Ir1 C13 C18 157.7(5) . . . .
C12 Ir1 C13 C18 121.6(6) . . . .
Cl1 Ir1 C13 C18 44.0(5) . . . .
C12 C13 C14 C15 -2.3(6) . . . .
C18 C13 C14 C15 -176.7(5) . . . .
Ir1 C13 C14 C15 60.5(3) . . . .
C12 C13 C14 C19 175.6(5) . . . .
C18 C13 C14 C19 1.3(8) . . . .
Ir1 C13 C14 C19 -121.6(5) . . . .
C12 C13 C14 Ir1 -62.8(3) . . . .
C18 C13 C14 Ir1 122.8(5) . . . .
N5 Ir1 C14 C15 117.6(3) . . . .
N3 Ir1 C14 C15 58.0(4) . . . .
C13 Ir1 C14 C15 -118.7(4) . . . .
C16 Ir1 C14 C15 -38.4(3) . . . .
C12 Ir1 C14 C15 -80.2(3) . . . .
Cl1 Ir1 C14 C15 -141.8(3) . . . .
N5 Ir1 C14 C13 -123.6(3) . . . .
N3 Ir1 C14 C13 176.7(3) . . . .
C15 Ir1 C14 C13 118.7(4) . . . .
C16 Ir1 C14 C13 80.3(3) . . . .
C12 Ir1 C14 C13 38.5(3) . . . .
Cl1 Ir1 C14 C13 -23.1(4) . . . .
N5 Ir1 C14 C19 -3.4(5) . . . .
N3 Ir1 C14 C19 -63.0(5) . . . .
C15 Ir1 C14 C19 -121.0(6) . . . .
C13 Ir1 C14 C19 120.3(6) . . . .
C16 Ir1 C14 C19 -159.4(5) . . . .
C12 Ir1 C14 C19 158.8(5) . . . .
Cl1 Ir1 C14 C19 97.2(5) . . . .
C13 C14 C15 C16 2.0(6) . . . .
C19 C14 C15 C16 -175.9(5) . . . .
Ir1 C14 C15 C16 62.4(3) . . . .
C13 C14 C15 C20 179.0(5) . . . .
C19 C14 C15 C20 1.1(8) . . . .
Ir1 C14 C15 C20 -120.7(5) . . . .
C13 C14 C15 Ir1 -60.3(3) . . . .
C19 C14 C15 Ir1 121.8(5) . . . .
N5 Ir1 C15 C14 -76.2(3) . . . .
N3 Ir1 C15 C14 -138.0(3) . . . .
C13 Ir1 C15 C14 37.6(3) . . . .
C16 Ir1 C15 C14 117.1(4) . . . .
C12 Ir1 C15 C14 80.9(3) . . . .
Cl1 Ir1 C15 C14 110.7(4) . . . .
N5 Ir1 C15 C16 166.7(3) . . . .
N3 Ir1 C15 C16 105.0(3) . . . .
C13 Ir1 C15 C16 -79.4(3) . . . .
C14 Ir1 C15 C16 -117.1(4) . . . .
C12 Ir1 C15 C16 -36.2(3) . . . .
Cl1 Ir1 C15 C16 -6.4(6) . . . .
N5 Ir1 C15 C20 47.0(5) . . . .
N3 Ir1 C15 C20 -14.8(5) . . . .
C13 Ir1 C15 C20 160.8(5) . . . .
C14 Ir1 C15 C20 123.2(6) . . . .
C16 Ir1 C15 C20 -119.7(6) . . . .
C12 Ir1 C15 C20 -155.9(5) . . . .
Cl1 Ir1 C15 C20 -126.1(4) . . . .
C13 C12 C16 C15 -0.5(6) . . . .
C17 C12 C16 C15 179.5(5) . . . .
Ir1 C12 C16 C15 -59.5(3) . . . .
C13 C12 C16 C21 -177.3(5) . . . .
C17 C12 C16 C21 2.7(9) . . . .
Ir1 C12 C16 C21 123.7(6) . . . .
C13 C12 C16 Ir1 59.0(4) . . . .
C17 C12 C16 Ir1 -121.0(5) . . . .
C14 C15 C16 C12 -0.9(6) . . . .
C20 C15 C16 C12 -178.0(5) . . . .
Ir1 C15 C16 C12 60.9(4) . . . .
C14 C15 C16 C21 176.0(5) . . . .
C20 C15 C16 C21 -1.1(8) . . . .
Ir1 C15 C16 C21 -122.2(5) . . . .
C14 C15 C16 Ir1 -61.9(3) . . . .
C20 C15 C16 Ir1 121.1(5) . . . .
N5 Ir1 C16 C12 -147.3(4) . . . .
N3 Ir1 C16 C12 153.2(3) . . . .
C15 Ir1 C16 C12 -119.1(4) . . . .
C13 Ir1 C16 C12 -37.4(3) . . . .
C14 Ir1 C16 C12 -81.1(3) . . . .
Cl1 Ir1 C16 C12 58.1(3) . . . .
N5 Ir1 C16 C15 -28.2(6) . . . .
N3 Ir1 C16 C15 -87.7(3) . . . .
C13 Ir1 C16 C15 81.7(3) . . . .
C14 Ir1 C16 C15 38.0(3) . . . .
C12 Ir1 C16 C15 119.1(4) . . . .
Cl1 Ir1 C16 C15 177.2(2) . . . .
N5 Ir1 C16 C21 88.9(6) . . . .
N3 Ir1 C16 C21 29.4(5) . . . .
C15 Ir1 C16 C21 117.1(6) . . . .
C13 Ir1 C16 C21 -161.2(5) . . . .
C14 Ir1 C16 C21 155.1(6) . . . .
C12 Ir1 C16 C21 -123.8(6) . . . .
Cl1 Ir1 C16 C21 -65.7(5) . . . .
