#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:01:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180165 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/61/7106112.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_7106112
loop_
_publ_author_name
' Jean-Pierre Djukic'
'Wissam Iali'
'Michel Pfeffer'
'Xavier-Frederic Le Goff'
_publ_section_title
;
 Charge-induced facial-selectivity in the formation of new cationic planar
 chiral iridacycles derived from aniline
;
_journal_name_full               Chem.Commun.
_journal_page_first              3631
_journal_paper_doi               10.1039/c0cc05711h
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C23 H28 Cl Ir N2'
_chemical_formula_sum            'C23 H28 Cl Ir N2'
_chemical_formula_weight         560.12
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_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                 128.903(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5371(6)
_cell_length_b                   7.5131(3)
_cell_length_c                   20.9885(6)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.08
_cell_measurement_theta_min      2.98
_cell_volume                     2029.35(14)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20707
_diffrn_reflns_theta_full        32.08
_diffrn_reflns_theta_max         32.08
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    6.721
_exptl_absorpt_correction_T_max  0.3467
_exptl_absorpt_correction_T_min  0.1844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         2.898
_refine_diff_density_min         -1.453
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         7014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0231
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0166P)²+4.1026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0504
_refine_ls_wR_factor_ref         0.0523
_reflns_number_gt                6324
_reflns_number_total             7014
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c0cc05711h.txt
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2029.35(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7106112
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 -0.267470(6) -0.258435(10) -0.998843(5) 0.01386(3) Uani 1 1 d . . .
Cl1 Cl -0.32964(5) -0.54194(8) -1.06777(4) 0.02188(11) Uani 1 1 d . . .
N1 N -0.29354(16) -0.3639(3) -0.92061(13) 0.0166(4) Uani 1 1 d . . .
N2 N 0.13504(18) -0.4641(4) -0.84389(16) 0.0290(5) Uani 1 1 d . . .
C1 C -0.12850(18) -0.3758(3) -0.91031(14) 0.0150(4) Uani 1 1 d . . .
C2 C -0.04238(19) -0.3782(3) -0.90755(15) 0.0181(4) Uani 1 1 d . . .
H2 H -0.0467 -0.3205 -0.9499 0.022 Uiso 1 1 calc R . .
C3 C 0.05145(19) -0.4634(3) -0.84412(15) 0.0198(4) Uani 1 1 d . . .
C4 C 0.0559(2) -0.5514(3) -0.78263(16) 0.0227(5) Uani 1 1 d . . .
H4 H 0.1179 -0.6103 -0.7394 0.027 Uiso 1 1 calc R . .
C5 C -0.0293(2) -0.5524(3) -0.78481(15) 0.0207(5) Uani 1 1 d . . .
H5 H -0.0257 -0.6139 -0.7435 0.025 Uiso 1 1 calc R . .
C6 C -0.12093(18) -0.4639(3) -0.84718(14) 0.0158(4) Uani 1 1 d . . .
C7 C -0.21354(19) -0.4569(3) -0.85414(14) 0.0170(4) Uani 1 1 d . . .
C8 C -0.2266(2) -0.5366(3) -0.80067(16) 0.0229(5) Uani 1 1 d . . .
H8 H -0.1706 -0.5990 -0.7537 0.027 Uiso 1 1 calc R . .
C9 C -0.3209(2) -0.5245(4) -0.81630(17) 0.0270(5) Uani 1 1 d . . .
H9 H -0.3301 -0.5788 -0.7804 0.032 Uiso 1 1 calc R . .
C10 C -0.4024(2) -0.4322(4) -0.88505(18) 0.0268(5) Uani 1 1 d . . .
H10 H -0.4680 -0.4227 -0.8971 0.032 Uiso 1 1 calc R . .
C11 C -0.3852(2) -0.3550(4) -0.93532(17) 0.0228(5) Uani 1 1 d . . .
H11 H -0.4408 -0.2926 -0.9825 0.027 Uiso 1 1 calc R . .
C12 C 0.2370(2) -0.5113(5) -0.76996(19) 0.0338(7) Uani 1 1 d . . .
H12A H 0.2564 -0.4307 -0.7256 0.051 Uiso 1 1 calc R . .
H12B H 0.2878 -0.5011 -0.7794 0.051 Uiso 1 1 calc R . .
H12C H 0.2359 -0.6340 -0.7547 0.051 Uiso 1 1 calc R . .
C13 C 0.1321(2) -0.3572(5) -0.9026(2) 0.0342(7) Uani 1 1 d . . .
H13A H 0.0746 -0.3968 -0.9581 0.051 Uiso 1 1 calc R . .
H13B H 0.1978 -0.3702 -0.8932 0.051 Uiso 1 1 calc R . .
H13C H 0.1219 -0.2319 -0.8962 0.051 Uiso 1 1 calc R . .
C14 C -0.2426(2) -0.0894(3) -1.06843(14) 0.0182(4) Uani 1 1 d . . .
C15 C -0.20860(19) 0.0023(3) -0.99487(14) 0.0165(4) Uani 1 1 d . . .
C16 C -0.2977(2) 0.0214(3) -0.99808(15) 0.0177(4) Uani 1 1 d . . .
C17 C -0.3885(2) -0.0456(3) -1.07653(16) 0.0209(5) Uani 1 1 d . . .
C18 C -0.3538(2) -0.1134(3) -1.11821(15) 0.0202(4) Uani 1 1 d . . .
C19 C -0.1779(2) -0.1286(4) -1.09422(18) 0.0267(5) Uani 1 1 d . . .
H19A H -0.2017 -0.0550 -1.1417 0.040 Uiso 1 1 calc R . .
H19B H -0.1848 -0.2547 -1.1089 0.040 Uiso 1 1 calc R . .
H19C H -0.1049 -0.1017 -1.0490 0.040 Uiso 1 1 calc R . .
C20 C -0.1043(2) 0.0796(4) -0.93120(16) 0.0246(5) Uani 1 1 d . . .
H20A H -0.1026 0.2028 -0.9456 0.037 Uiso 1 1 calc R . .
H20B H -0.0516 0.0096 -0.9277 0.037 Uiso 1 1 calc R . .
H20C H -0.0897 0.0773 -0.8782 0.037 Uiso 1 1 calc R . .
C21 C -0.3000(2) 0.1134(4) -0.93623(18) 0.0258(5) Uani 1 1 d . . .
H21A H -0.2293 0.1211 -0.8841 0.039 Uiso 1 1 calc R . .
H21B H -0.3438 0.0460 -0.9283 0.039 Uiso 1 1 calc R . .
H21C H -0.3284 0.2336 -0.9556 0.039 Uiso 1 1 calc R . .
C22 C -0.4982(2) -0.0315(4) -1.1086(2) 0.0337(7) Uani 1 1 d . . .
H22A H -0.5303 0.0749 -1.1430 0.050 Uiso 1 1 calc R . .
H22B H -0.4995 -0.0228 -1.0627 0.050 Uiso 1 1 calc R . .
H22C H -0.5369 -0.1373 -1.1412 0.050 Uiso 1 1 calc R . .
C23 C -0.4212(3) -0.1961(4) -1.20203(17) 0.0325(6) Uani 1 1 d . . .
H23A H -0.4681 -0.2830 -1.2055 0.049 Uiso 1 1 calc R . .
H23B H -0.3774 -0.2560 -1.2119 0.049 Uiso 1 1 calc R . .
H23C H -0.4623 -0.1031 -1.2433 0.049 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'
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'
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
C1 Ir1 N1 77.94(9) . . ?
C1 Ir1 C14 106.65(9) . . ?
N1 Ir1 C14 166.19(9) . . ?
C1 Ir1 C16 123.20(9) . . ?
N1 Ir1 C16 101.49(9) . . ?
C14 Ir1 C16 64.96(9) . . ?
C1 Ir1 C15 97.70(9) . . ?
N1 Ir1 C15 128.32(8) . . ?
C14 Ir1 C15 38.97(9) . . ?
C16 Ir1 C15 38.85(9) . . ?
C1 Ir1 C18 142.46(9) . . ?
N1 Ir1 C18 139.48(9) . . ?
C14 Ir1 C18 38.33(9) . . ?
C16 Ir1 C18 63.09(9) . . ?
C15 Ir1 C18 63.77(9) . . ?
C1 Ir1 C17 160.69(10) . . ?
N1 Ir1 C17 107.92(9) . . ?
C14 Ir1 C17 63.57(10) . . ?
C16 Ir1 C17 38.26(9) . . ?
C15 Ir1 C17 63.98(9) . . ?
C18 Ir1 C17 36.47(9) . . ?
C1 Ir1 Cl1 88.67(7) . . ?
N1 Ir1 Cl1 85.19(6) . . ?
C14 Ir1 Cl1 107.70(7) . . ?
C16 Ir1 Cl1 148.11(7) . . ?
C15 Ir1 Cl1 146.49(6) . . ?
C18 Ir1 Cl1 91.51(7) . . ?
C17 Ir1 Cl1 109.92(7) . . ?
C11 N1 C7 119.2(2) . . ?
C11 N1 Ir1 123.89(18) . . ?
C7 N1 Ir1 116.71(16) . . ?
C3 N2 C13 119.8(2) . . ?
C3 N2 C12 119.7(3) . . ?
C13 N2 C12 116.3(3) . . ?
C2 C1 C6 118.0(2) . . ?
C2 C1 Ir1 125.72(17) . . ?
C6 C1 Ir1 116.28(17) . . ?
C1 C2 C3 122.4(2) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
N2 C3 C4 121.3(2) . . ?
N2 C3 C2 120.7(2) . . ?
C4 C3 C2 118.0(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 C7 124.6(2) . . ?
C1 C6 C7 115.0(2) . . ?
N1 C7 C8 119.9(2) . . ?
N1 C7 C6 114.0(2) . . ?
C8 C7 C6 126.1(2) . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 118.1(3) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
N1 C11 C10 123.1(3) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C18 107.3(2) . . ?
C15 C14 C19 126.3(2) . . ?
C18 C14 C19 125.8(2) . . ?
C15 C14 Ir1 70.70(13) . . ?
C18 C14 Ir1 73.73(14) . . ?
C19 C14 Ir1 127.56(18) . . ?
C16 C15 C14 107.3(2) . . ?
C16 C15 C20 125.5(2) . . ?
C14 C15 C20 127.0(2) . . ?
C16 C15 Ir1 70.48(13) . . ?
C14 C15 Ir1 70.33(13) . . ?
C20 C15 Ir1 128.94(17) . . ?
C15 C16 C17 108.5(2) . . ?
C15 C16 C21 126.1(2) . . ?
C17 C16 C21 125.0(2) . . ?
C15 C16 Ir1 70.67(13) . . ?
C17 C16 Ir1 74.58(13) . . ?
C21 C16 Ir1 126.10(17) . . ?
C18 C17 C16 107.2(2) . . ?
C18 C17 C22 126.9(3) . . ?
C16 C17 C22 125.8(2) . . ?
C18 C17 Ir1 70.82(14) . . ?
C16 C17 Ir1 67.16(13) . . ?
C22 C17 Ir1 130.6(2) . . ?
C17 C18 C14 109.5(2) . . ?
C17 C18 C23 125.7(3) . . ?
C14 C18 C23 124.7(2) . . ?
C17 C18 Ir1 72.71(14) . . ?
C14 C18 Ir1 67.94(13) . . ?
C23 C18 Ir1 126.29(19) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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 C1 2.037(2) . ?
Ir1 N1 2.097(2) . ?
Ir1 C14 2.161(2) . ?
Ir1 C16 2.163(2) . ?
Ir1 C15 2.166(2) . ?
Ir1 C18 2.238(2) . ?
Ir1 C17 2.263(2) . ?
Ir1 Cl1 2.4122(6) . ?
N1 C11 1.346(3) . ?
N1 C7 1.366(3) . ?
N2 C3 1.379(3) . ?
N2 C13 1.446(4) . ?
N2 C12 1.446(4) . ?
C1 C2 1.389(3) . ?
C1 C6 1.415(3) . ?
C2 C3 1.413(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(4) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.445(3) . ?
C7 C8 1.404(3) . ?
C8 C9 1.379(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.443(3) . ?
C14 C18 1.446(4) . ?
C14 C19 1.501(4) . ?
C15 C16 1.440(3) . ?
C15 C20 1.484(4) . ?
C16 C17 1.454(4) . ?
C16 C21 1.492(3) . ?
C17 C18 1.409(4) . ?
C17 C22 1.491(4) . ?
C18 C23 1.503(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
_geom_torsion_publ_flag
C1 Ir1 N1 C11 -176.8(2) . . . . ?
C14 Ir1 N1 C11 72.2(4) . . . . ?
C16 Ir1 N1 C11 61.3(2) . . . . ?
C15 Ir1 N1 C11 92.9(2) . . . . ?
C18 Ir1 N1 C11 -0.4(3) . . . . ?
C17 Ir1 N1 C11 22.3(2) . . . . ?
Cl1 Ir1 N1 C11 -87.14(19) . . . . ?
C1 Ir1 N1 C7 -1.37(17) . . . . ?
C14 Ir1 N1 C7 -112.4(4) . . . . ?
C16 Ir1 N1 C7 -123.23(17) . . . . ?
C15 Ir1 N1 C7 -91.70(19) . . . . ?
C18 Ir1 N1 C7 174.99(16) . . . . ?
C17 Ir1 N1 C7 -162.30(16) . . . . ?
Cl1 Ir1 N1 C7 88.30(16) . . . . ?
N1 Ir1 C1 C2 -179.9(2) . . . . ?
C14 Ir1 C1 C2 -13.4(2) . . . . ?
C16 Ir1 C1 C2 -84.0(2) . . . . ?
C15 Ir1 C1 C2 -52.3(2) . . . . ?
C18 Ir1 C1 C2 4.0(3) . . . . ?
C17 Ir1 C1 C2 -69.9(4) . . . . ?
Cl1 Ir1 C1 C2 94.7(2) . . . . ?
N1 Ir1 C1 C6 0.98(16) . . . . ?
C14 Ir1 C1 C6 167.52(17) . . . . ?
C16 Ir1 C1 C6 96.93(18) . . . . ?
C15 Ir1 C1 C6 128.64(17) . . . . ?
C18 Ir1 C1 C6 -175.14(16) . . . . ?
C17 Ir1 C1 C6 111.0(3) . . . . ?
Cl1 Ir1 C1 C6 -84.39(17) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
Ir1 C1 C2 C3 -179.67(18) . . . . ?
C13 N2 C3 C4 -173.4(3) . . . . ?
C12 N2 C3 C4 -17.1(4) . . . . ?
C13 N2 C3 C2 8.4(4) . . . . ?
C12 N2 C3 C2 164.6(3) . . . . ?
C1 C2 C3 N2 179.5(2) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
N2 C3 C4 C5 -178.6(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
Ir1 C1 C6 C5 178.32(18) . . . . ?
C2 C1 C6 C7 -179.7(2) . . . . ?
Ir1 C1 C6 C7 -0.5(3) . . . . ?
C11 N1 C7 C8 -2.1(3) . . . . ?
Ir1 N1 C7 C8 -177.76(18) . . . . ?
C11 N1 C7 C6 177.1(2) . . . . ?
Ir1 N1 C7 C6 1.5(3) . . . . ?
C5 C6 C7 N1 -179.4(2) . . . . ?
C1 C6 C7 N1 -0.6(3) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C1 C6 C7 C8 178.6(2) . . . . ?
N1 C7 C8 C9 1.5(4) . . . . ?
C6 C7 C8 C9 -177.7(2) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C7 N1 C11 C10 1.6(4) . . . . ?
Ir1 N1 C11 C10 177.0(2) . . . . ?
C9 C10 C11 N1 -0.4(4) . . . . ?
C1 Ir1 C14 C15 -81.53(15) . . . . ?
N1 Ir1 C14 C15 26.1(4) . . . . ?
C16 Ir1 C14 C15 37.88(14) . . . . ?
C18 Ir1 C14 C15 115.5(2) . . . . ?
C17 Ir1 C14 C15 80.52(15) . . . . ?
Cl1 Ir1 C14 C15 -175.54(12) . . . . ?
C1 Ir1 C14 C18 162.97(14) . . . . ?
N1 Ir1 C14 C18 -89.4(4) . . . . ?
C16 Ir1 C14 C18 -77.62(15) . . . . ?
C15 Ir1 C14 C18 -115.5(2) . . . . ?
C17 Ir1 C14 C18 -34.98(14) . . . . ?
Cl1 Ir1 C14 C18 68.96(14) . . . . ?
C1 Ir1 C14 C19 39.9(3) . . . . ?
N1 Ir1 C14 C19 147.6(3) . . . . ?
C16 Ir1 C14 C19 159.4(3) . . . . ?
C15 Ir1 C14 C19 121.5(3) . . . . ?
C18 Ir1 C14 C19 -123.0(3) . . . . ?
C17 Ir1 C14 C19 -158.0(3) . . . . ?
Cl1 Ir1 C14 C19 -54.1(2) . . . . ?
C18 C14 C15 C16 4.0(3) . . . . ?
C19 C14 C15 C16 175.9(2) . . . . ?
Ir1 C14 C15 C16 -61.12(15) . . . . ?
C18 C14 C15 C20 -170.3(2) . . . . ?
C19 C14 C15 C20 1.5(4) . . . . ?
Ir1 C14 C15 C20 124.5(2) . . . . ?
C18 C14 C15 Ir1 65.17(16) . . . . ?
C19 C14 C15 Ir1 -123.0(2) . . . . ?
C1 Ir1 C15 C16 -135.48(14) . . . . ?
N1 Ir1 C15 C16 -54.79(17) . . . . ?
C14 Ir1 C15 C16 117.5(2) . . . . ?
C18 Ir1 C15 C16 78.90(15) . . . . ?
C17 Ir1 C15 C16 38.11(14) . . . . ?
Cl1 Ir1 C15 C16 125.22(13) . . . . ?
C1 Ir1 C15 C14 107.02(15) . . . . ?
N1 Ir1 C15 C14 -172.30(13) . . . . ?
C16 Ir1 C15 C14 -117.5(2) . . . . ?
C18 Ir1 C15 C14 -38.61(14) . . . . ?
C17 Ir1 C15 C14 -79.40(15) . . . . ?
Cl1 Ir1 C15 C14 7.7(2) . . . . ?
C1 Ir1 C15 C20 -15.2(2) . . . . ?
N1 Ir1 C15 C20 65.5(3) . . . . ?
C14 Ir1 C15 C20 -122.2(3) . . . . ?
C16 Ir1 C15 C20 120.3(3) . . . . ?
C18 Ir1 C15 C20 -160.8(3) . . . . ?
C17 Ir1 C15 C20 158.4(3) . . . . ?
Cl1 Ir1 C15 C20 -114.5(2) . . . . ?
C14 C15 C16 C17 -4.5(3) . . . . ?
C20 C15 C16 C17 170.0(2) . . . . ?
Ir1 C15 C16 C17 -65.53(16) . . . . ?
C14 C15 C16 C21 -177.9(2) . . . . ?
C20 C15 C16 C21 -3.4(4) . . . . ?
Ir1 C15 C16 C21 121.1(2) . . . . ?
C14 C15 C16 Ir1 61.02(15) . . . . ?
C20 C15 C16 Ir1 -124.5(2) . . . . ?
C1 Ir1 C16 C15 56.14(17) . . . . ?
N1 Ir1 C16 C15 139.15(13) . . . . ?
C14 Ir1 C16 C15 -38.01(13) . . . . ?
C18 Ir1 C16 C15 -80.80(15) . . . . ?
C17 Ir1 C16 C15 -116.4(2) . . . . ?
Cl1 Ir1 C16 C15 -121.37(14) . . . . ?
C1 Ir1 C16 C17 172.56(14) . . . . ?
N1 Ir1 C16 C17 -104.43(15) . . . . ?
C14 Ir1 C16 C17 78.41(16) . . . . ?
C15 Ir1 C16 C17 116.4(2) . . . . ?
C18 Ir1 C16 C17 35.63(15) . . . . ?
Cl1 Ir1 C16 C17 -5.0(2) . . . . ?
C1 Ir1 C16 C21 -65.0(3) . . . . ?
N1 Ir1 C16 C21 18.0(2) . . . . ?
C14 Ir1 C16 C21 -159.2(3) . . . . ?
C15 Ir1 C16 C21 -121.2(3) . . . . ?
C18 Ir1 C16 C21 158.0(3) . . . . ?
C17 Ir1 C16 C21 122.4(3) . . . . ?
Cl1 Ir1 C16 C21 117.5(2) . . . . ?
C15 C16 C17 C18 3.2(3) . . . . ?
C21 C16 C17 C18 176.7(2) . . . . ?
Ir1 C16 C17 C18 -59.77(17) . . . . ?
C15 C16 C17 C22 -172.5(2) . . . . ?
C21 C16 C17 C22 0.9(4) . . . . ?
Ir1 C16 C17 C22 124.5(3) . . . . ?
C15 C16 C17 Ir1 62.99(15) . . . . ?
C21 C16 C17 Ir1 -123.6(2) . . . . ?
C1 Ir1 C17 C18 100.0(3) . . . . ?
N1 Ir1 C17 C18 -155.04(15) . . . . ?
C14 Ir1 C17 C18 36.74(15) . . . . ?
C16 Ir1 C17 C18 119.1(2) . . . . ?
C15 Ir1 C17 C18 80.40(16) . . . . ?
Cl1 Ir1 C17 C18 -63.69(16) . . . . ?
C1 Ir1 C17 C16 -19.1(4) . . . . ?
N1 Ir1 C17 C16 85.88(15) . . . . ?
C14 Ir1 C17 C16 -82.35(16) . . . . ?
C15 Ir1 C17 C16 -38.69(14) . . . . ?
C18 Ir1 C17 C16 -119.1(2) . . . . ?
Cl1 Ir1 C17 C16 177.22(13) . . . . ?
C1 Ir1 C17 C22 -137.5(3) . . . . ?
N1 Ir1 C17 C22 -32.5(3) . . . . ?
C14 Ir1 C17 C22 159.3(3) . . . . ?
C16 Ir1 C17 C22 -118.3(3) . . . . ?
C15 Ir1 C17 C22 -157.0(3) . . . . ?
C18 Ir1 C17 C22 122.6(3) . . . . ?
Cl1 Ir1 C17 C22 58.9(3) . . . . ?
C16 C17 C18 C14 -0.7(3) . . . . ?
C22 C17 C18 C14 175.0(3) . . . . ?
Ir1 C17 C18 C14 -58.14(17) . . . . ?
C16 C17 C18 C23 -179.9(2) . . . . ?
C22 C17 C18 C23 -4.2(4) . . . . ?
Ir1 C17 C18 C23 122.7(3) . . . . ?
C16 C17 C18 Ir1 57.47(16) . . . . ?
C22 C17 C18 Ir1 -126.8(3) . . . . ?
C15 C14 C18 C17 -2.1(3) . . . . ?
C19 C14 C18 C17 -174.0(2) . . . . ?
Ir1 C14 C18 C17 61.05(18) . . . . ?
C15 C14 C18 C23 177.1(2) . . . . ?
C19 C14 C18 C23 5.2(4) . . . . ?
Ir1 C14 C18 C23 -119.7(3) . . . . ?
C15 C14 C18 Ir1 -63.16(15) . . . . ?
C19 C14 C18 Ir1 124.9(2) . . . . ?
C1 Ir1 C18 C17 -147.69(16) . . . . ?
N1 Ir1 C18 C17 38.2(2) . . . . ?
C14 Ir1 C18 C17 -120.3(2) . . . . ?
C16 Ir1 C18 C17 -37.36(15) . . . . ?
C15 Ir1 C18 C17 -81.01(16) . . . . ?
Cl1 Ir1 C18 C17 122.53(14) . . . . ?
C1 Ir1 C18 C14 -27.4(2) . . . . ?
N1 Ir1 C18 C14 158.44(14) . . . . ?
C16 Ir1 C18 C14 82.91(15) . . . . ?
C15 Ir1 C18 C14 39.26(14) . . . . ?
C17 Ir1 C18 C14 120.3(2) . . . . ?
Cl1 Ir1 C18 C14 -117.20(13) . . . . ?
C1 Ir1 C18 C23 90.3(3) . . . . ?
N1 Ir1 C18 C23 -83.8(3) . . . . ?
C14 Ir1 C18 C23 117.7(3) . . . . ?
C16 Ir1 C18 C23 -159.4(3) . . . . ?
C15 Ir1 C18 C23 157.0(3) . . . . ?
C17 Ir1 C18 C23 -122.0(3) . . . . ?
Cl1 Ir1 C18 C23 0.5(2) . . . . ?
