#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:30:18 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157757.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_7157757
loop_
_publ_author_name
'Smith, Jennifer'
'Kacmaz, Aysecik'
'Wang, Chao'
'Villa-Marcos, Barbara'
'Xiao, Jianliang'
_publ_section_title
;
 Chiral cyclometalated iridium complexes for asymmetric reduction
 reactions.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              279
_journal_page_last               284
_journal_paper_doi               10.1039/d0ob02049d
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety
'(Ir 3+), (Cl 1-), (C21 H16 O N 1-),(C10 H15 1-)'
_chemical_formula_sum            'C31 H31 Cl Ir N O'
_chemical_formula_weight         661.22
_chemical_name_common            'Chiral Iridicyle 1'
_chemical_name_systematic        'Chiral Iridicyle 1'
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-09-10 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 119.2660(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3621(9)
_cell_length_b                   11.4447(9)
_cell_length_c                   11.5177(9)
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.70
_cell_volume                     1306.54(18)
_computing_cell_refinement       'SAINT v6.45a (Bruker, 2005)'
_computing_data_collection       'SMART v.5.632 (Bruker, 2005)'
_computing_data_reduction        'SAINT v6.45a (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX detector'
_diffrn_measurement_method       'ω scans with a narrow frame width'
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7488
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    5.236
_exptl_absorpt_correction_T_max  0.4207
_exptl_absorpt_correction_T_min  0.2285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008-1 (Sheldrick, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.078
_refine_diff_density_min         -1.196
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.748
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5206
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.747
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0197
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0442
_refine_ls_wR_factor_ref         0.0445
_reflns_number_gt                5001
_reflns_number_total             5218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob02049d2.cif
_cod_data_source_block           added_by_encifer
_cod_depositor_comments
'Adding full bibliography for 7157757--7157758.cif.'
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7157757
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Ir1 Ir Uani 0.73185(1) 0.18552(2) 0.46836(1) 1.000 0.0090(1) . .
Cl1 Cl Uani 0.69970(9) 0.23816(8) 0.65280(9) 1.000 0.0138(3) . .
O1 O Uani 0.3303(3) 0.2890(2) 0.2780(3) 1.000 0.0136(9) . .
N1 N Uani 0.5217(2) 0.1858(5) 0.3583(2) 1.000 0.0113(7) . .
C2 C Uani 0.4669(4) 0.2852(4) 0.3336(5) 1.000 0.0131(12) . .
C3 C Uani 0.4136(4) 0.0949(4) 0.3031(4) 1.000 0.0091(11) . .
C4 C Uani 0.2947(3) 0.1689(4) 0.2948(3) 1.000 0.0118(12) . .
C5 C Uani 0.5494(4) 0.3884(3) 0.3598(4) 1.000 0.0118(11) . .
C6 C Uani 0.5011(4) 0.5027(3) 0.3314(4) 1.000 0.0161(12) . .
C7 C Uani 0.5923(4) 0.5921(3) 0.3593(4) 1.000 0.0146(11) . .
C8 C Uani 0.7296(4) 0.5662(3) 0.4170(4) 1.000 0.0145(12) . .
C9 C Uani 0.7769(4) 0.4517(4) 0.4483(4) 1.000 0.0140(12) . .
C10 C Uani 0.6881(4) 0.3587(3) 0.4191(4) 1.000 0.0110(11) . .
C11 C Uani 0.3930(4) 0.0511(3) 0.1700(4) 1.000 0.0127(11) . .
C12 C Uani 0.3971(4) 0.1271(4) 0.0771(4) 1.000 0.0166(12) . .
C13 C Uani 0.3804(4) 0.0848(4) -0.0427(4) 1.000 0.0215(14) . .
C14 C Uani 0.3608(4) -0.0326(4) -0.0719(4) 1.000 0.0258(14) . .
C15 C Uani 0.3555(4) -0.1092(4) 0.0185(5) 1.000 0.0256(16) . .
C16 C Uani 0.3716(4) -0.0673(4) 0.1390(4) 1.000 0.0188(12) . .
C17 C Uani 0.1533(4) 0.1399(3) 0.1899(4) 1.000 0.0122(11) . .
C18 C Uani 0.0701(4) 0.2218(3) 0.0976(4) 1.000 0.0174(12) . .
C19 C Uani -0.0629(3) 0.1943(7) 0.0064(3) 1.000 0.0200(10) . .
C20 C Uani -0.1122(4) 0.0837(4) 0.0071(4) 1.000 0.0220(14) . .
C21 C Uani -0.0289(4) 0.0015(4) 0.0989(4) 1.000 0.0188(12) . .
C22 C Uani 0.1036(4) 0.0281(4) 0.1906(4) 1.000 0.0159(11) . .
C23 C Uani 0.7984(4) 0.0715(3) 0.3629(4) 1.000 0.0115(11) . .
C24 C Uani 0.7968(4) 0.0003(4) 0.4669(4) 1.000 0.0126(12) . .
C25 C Uani 0.8875(4) 0.0505(3) 0.5909(4) 1.000 0.0132(11) . .
C26 C Uani 0.9458(4) 0.1566(3) 0.5670(4) 1.000 0.0142(13) . .
C27 C Uani 0.8946(3) 0.1640(3) 0.4258(4) 1.000 0.0113(13) . .
C28 C Uani 0.7300(4) 0.0403(4) 0.2179(4) 1.000 0.0163(12) . .
C29 C Uani 0.7149(4) -0.1076(4) 0.4450(4) 1.000 0.0181(12) . .
C30 C Uani 0.9201(4) 0.0083(4) 0.7251(4) 1.000 0.0178(12) . .
C31 C Uani 1.0499(4) 0.2317(4) 0.6762(4) 1.000 0.0190(11) . .
C32 C Uani 0.9380(4) 0.2478(3) 0.3537(4) 1.000 0.0169(12) . .
H3 H Uiso 0.43580 0.02870 0.36720 1.000 0.024(8) calc R
H4 H Uiso 0.29850 0.16430 0.38330 1.000 0.024(8) calc R
H6 H Uiso 0.40740 0.51850 0.29380 1.000 0.015(5) calc R
H7 H Uiso 0.56200 0.67070 0.33930 1.000 0.015(5) calc R
H8 H Uiso 0.79220 0.62790 0.43540 1.000 0.015(5) calc R
H9 H Uiso 0.87110 0.43710 0.49010 1.000 0.015(5) calc R
H12 H Uiso 0.41140 0.20830 0.09620 1.000 0.022(6) calc R
H13 H Uiso 0.38260 0.13740 -0.10550 1.000 0.022(6) calc R
H14 H Uiso 0.35100 -0.06100 -0.15370 1.000 0.022(6) calc R
H15 H Uiso 0.34080 -0.19020 -0.00160 1.000 0.022(6) calc R
H16 H Uiso 0.36800 -0.12010 0.20080 1.000 0.022(6) calc R
H18 H Uiso 0.10410 0.29750 0.09670 1.000 0.024(6) calc R
H19 H Uiso -0.11970 0.25100 -0.05620 1.000 0.024(6) calc R
H20 H Uiso -0.20290 0.06430 -0.05510 1.000 0.024(6) calc R
H21 H Uiso -0.06320 -0.07420 0.09890 1.000 0.024(6) calc R
H22 H Uiso 0.16010 -0.02880 0.25310 1.000 0.024(6) calc R
H28A H Uiso 0.71700 0.11110 0.16510 1.000 0.027(7) calc R
H28B H Uiso 0.64210 0.00480 0.19210 1.000 0.027(7) calc R
H28C H Uiso 0.78610 -0.01520 0.20190 1.000 0.027(7) calc R
H29A H Uiso 0.76730 -0.17600 0.44590 1.000 0.031(4) calc R
H29B H Uiso 0.63220 -0.10270 0.35870 1.000 0.031(4) calc R
H29C H Uiso 0.69140 -0.11510 0.51600 1.000 0.031(4) calc R
H30A H Uiso 0.85400 -0.05080 0.71680 1.000 0.031(4) calc R
H30B H Uiso 0.91710 0.07410 0.77820 1.000 0.031(4) calc R
H30C H Uiso 1.01060 -0.02610 0.76910 1.000 0.031(4) calc R
H31A H Uiso 1.13800 0.19290 0.71500 1.000 0.031(4) calc R
H31B H Uiso 1.02450 0.24340 0.74530 1.000 0.031(4) calc R
H31C H Uiso 1.05520 0.30750 0.63940 1.000 0.031(4) calc R
H32A H Uiso 0.97630 0.31800 0.40810 1.000 0.031(4) calc R
H32B H Uiso 0.85980 0.26950 0.26860 1.000 0.031(4) calc R
H32C H Uiso 1.00620 0.21060 0.33740 1.000 0.031(4) 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'
O O 0.0106 0.0060 '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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Ir1 N1 85.02(7) . . . yes
Cl1 Ir1 C10 83.19(12) . . . yes
Cl1 Ir1 C23 153.78(10) . . . yes
Cl1 Ir1 C24 115.83(11) . . . yes
Cl1 Ir1 C25 91.73(11) . . . yes
Cl1 Ir1 C26 101.13(11) . . . yes
Cl1 Ir1 C27 138.71(11) . . . yes
N1 Ir1 C10 77.3(2) . . . yes
N1 Ir1 C23 105.73(16) . . . yes
N1 Ir1 C24 106.2(2) . . . yes
N1 Ir1 C25 134.21(19) . . . yes
N1 Ir1 C26 170.29(17) . . . yes
N1 Ir1 C27 136.02(13) . . . yes
C10 Ir1 C23 122.17(16) . . . yes
C10 Ir1 C24 160.71(17) . . . yes
C10 Ir1 C25 147.69(17) . . . yes
C10 Ir1 C26 110.69(17) . . . yes
C10 Ir1 C27 99.60(17) . . . yes
C23 Ir1 C24 38.55(15) . . . yes
C23 Ir1 C25 63.47(15) . . . yes
C23 Ir1 C26 65.58(16) . . . yes
C23 Ir1 C27 39.04(15) . . . yes
C24 Ir1 C25 36.58(14) . . . yes
C24 Ir1 C26 64.38(15) . . . yes
C24 Ir1 C27 64.36(16) . . . yes
C25 Ir1 C26 39.02(15) . . . yes
C25 Ir1 C27 64.15(16) . . . yes
C26 Ir1 C27 39.11(16) . . . yes
C2 O1 C4 103.4(3) . . . yes
Ir1 N1 C2 115.5(4) . . . yes
Ir1 N1 C3 135.8(4) . . . yes
C2 N1 C3 108.7(3) . . . yes
O1 C2 N1 117.3(4) . . . yes
O1 C2 C5 123.1(4) . . . yes
N1 C2 C5 119.5(5) . . . yes
N1 C3 C4 99.0(3) . . . yes
N1 C3 C11 110.4(4) . . . yes
C4 C3 C11 114.6(3) . . . no
O1 C4 C3 103.3(3) . . . yes
O1 C4 C17 110.8(3) . . . yes
C3 C4 C17 119.0(3) . . . no
C2 C5 C6 125.3(4) . . . no
C2 C5 C10 111.1(3) . . . no
C6 C5 C10 123.7(4) . . . no
C5 C6 C7 118.5(4) . . . no
C6 C7 C8 119.4(3) . . . no
C7 C8 C9 121.5(4) . . . no
C8 C9 C10 121.0(4) . . . no
Ir1 C10 C5 115.2(3) . . . yes
Ir1 C10 C9 128.5(3) . . . yes
C5 C10 C9 115.9(3) . . . no
C3 C11 C12 121.4(3) . . . no
C3 C11 C16 120.1(4) . . . no
C12 C11 C16 118.5(4) . . . no
C11 C12 C13 120.4(4) . . . no
C12 C13 C14 120.8(4) . . . no
C13 C14 C15 119.7(4) . . . no
C14 C15 C16 119.9(4) . . . no
C11 C16 C15 120.8(4) . . . no
C4 C17 C18 121.9(4) . . . no
C4 C17 C22 118.3(4) . . . no
C18 C17 C22 119.8(4) . . . no
C17 C18 C19 120.6(4) . . . no
C18 C19 C20 119.7(5) . . . no
C19 C20 C21 119.8(4) . . . no
C20 C21 C22 121.0(4) . . . no
C17 C22 C21 119.2(4) . . . no
Ir1 C23 C24 74.1(3) . . . yes
Ir1 C23 C27 70.1(2) . . . yes
Ir1 C23 C28 129.6(3) . . . yes
C24 C23 C27 108.0(3) . . . no
C24 C23 C28 125.1(4) . . . no
C27 C23 C28 126.1(4) . . . no
Ir1 C24 C23 67.3(2) . . . yes
Ir1 C24 C25 71.9(2) . . . yes
Ir1 C24 C29 127.0(3) . . . yes
C23 C24 C25 107.9(4) . . . no
C23 C24 C29 125.6(4) . . . no
C25 C24 C29 126.5(4) . . . no
Ir1 C25 C24 71.6(3) . . . yes
Ir1 C25 C26 66.7(2) . . . yes
Ir1 C25 C30 126.6(3) . . . yes
C24 C25 C26 108.6(4) . . . no
C24 C25 C30 127.5(4) . . . no
C26 C25 C30 123.9(4) . . . no
Ir1 C26 C25 74.3(3) . . . yes
Ir1 C26 C27 70.4(2) . . . yes
Ir1 C26 C31 125.3(3) . . . yes
C25 C26 C27 106.9(3) . . . no
C25 C26 C31 123.8(4) . . . no
C27 C26 C31 129.1(4) . . . no
Ir1 C27 C23 70.8(2) . . . yes
Ir1 C27 C26 70.5(3) . . . yes
Ir1 C27 C32 127.3(3) . . . yes
C23 C27 C26 108.3(3) . . . no
C23 C27 C32 124.5(4) . . . no
C26 C27 C32 127.1(3) . . . no
N1 C3 H3 111.00 . . . no
C4 C3 H3 111.00 . . . no
C11 C3 H3 111.00 . . . no
O1 C4 H4 108.00 . . . no
C3 C4 H4 108.00 . . . no
C17 C4 H4 108.00 . . . no
C5 C6 H6 121.00 . . . no
C7 C6 H6 121.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C7 C8 H8 119.00 . . . no
C9 C8 H8 119.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C11 C16 H16 120.00 . . . no
C15 C16 H16 120.00 . . . no
C17 C18 H18 120.00 . . . no
C19 C18 H18 120.00 . . . no
C18 C19 H19 120.00 . . . no
C20 C19 H19 120.00 . . . no
C19 C20 H20 120.00 . . . no
C21 C20 H20 120.00 . . . no
C20 C21 H21 119.00 . . . no
C22 C21 H21 120.00 . . . no
C17 C22 H22 120.00 . . . no
C21 C22 H22 120.00 . . . no
C23 C28 H28A 109.00 . . . no
C23 C28 H28B 109.00 . . . no
C23 C28 H28C 109.00 . . . no
H28A C28 H28B 109.00 . . . no
H28A C28 H28C 110.00 . . . no
H28B C28 H28C 110.00 . . . no
C24 C29 H29A 109.00 . . . no
C24 C29 H29B 109.00 . . . no
C24 C29 H29C 109.00 . . . no
H29A C29 H29B 109.00 . . . no
H29A C29 H29C 109.00 . . . no
H29B C29 H29C 110.00 . . . no
C25 C30 H30A 110.00 . . . no
C25 C30 H30B 109.00 . . . no
C25 C30 H30C 110.00 . . . no
H30A C30 H30B 109.00 . . . no
H30A C30 H30C 109.00 . . . no
H30B C30 H30C 109.00 . . . no
C26 C31 H31A 109.00 . . . no
C26 C31 H31B 109.00 . . . no
C26 C31 H31C 109.00 . . . no
H31A C31 H31B 109.00 . . . no
H31A C31 H31C 109.00 . . . no
H31B C31 H31C 110.00 . . . no
C27 C32 H32A 109.00 . . . no
C27 C32 H32B 109.00 . . . no
C27 C32 H32C 109.00 . . . no
H32A C32 H32B 109.00 . . . no
H32A C32 H32C 109.00 . . . no
H32B C32 H32C 110.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 Cl1 2.4016(10) . . yes
Ir1 N1 2.085(2) . . yes
Ir1 C10 2.055(4) . . yes
Ir1 C23 2.156(4) . . yes
Ir1 C24 2.247(5) . . yes
Ir1 C25 2.251(4) . . yes
Ir1 C26 2.147(5) . . yes
Ir1 C27 2.146(4) . . yes
O1 C2 1.360(6) . . yes
O1 C4 1.472(5) . . yes
N1 C2 1.261(7) . . yes
N1 C3 1.494(6) . . yes
C2 C5 1.445(6) . . no
C3 C4 1.557(6) . . no
C3 C11 1.518(6) . . no
C4 C17 1.501(6) . . no
C5 C6 1.394(5) . . no
C5 C10 1.419(7) . . no
C6 C7 1.378(6) . . no
C7 C8 1.396(7) . . no
C8 C9 1.395(6) . . no
C9 C10 1.390(6) . . no
C11 C12 1.397(6) . . no
C11 C16 1.392(6) . . no
C12 C13 1.385(6) . . no
C13 C14 1.377(6) . . no
C14 C15 1.385(7) . . no
C15 C16 1.393(7) . . no
C17 C18 1.386(5) . . no
C17 C22 1.400(6) . . no
C18 C19 1.391(6) . . no
C19 C20 1.386(9) . . no
C20 C21 1.386(6) . . no
C21 C22 1.386(7) . . no
C23 C24 1.456(6) . . no
C23 C27 1.437(5) . . no
C23 C28 1.501(6) . . no
C24 C25 1.412(6) . . no
C24 C29 1.492(7) . . no
C25 C26 1.472(6) . . no
C25 C30 1.483(6) . . no
C26 C27 1.437(6) . . no
C26 C31 1.505(6) . . no
C27 C32 1.501(6) . . no
C3 H3 1.0000 . . no
C4 H4 1.0000 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C12 H12 0.9500 . . no
C13 H13 0.9500 . . no
C14 H14 0.9500 . . no
C15 H15 0.9500 . . no
C16 H16 0.9500 . . no
C18 H18 0.9500 . . no
C19 H19 0.9500 . . no
C20 H20 0.9500 . . no
C21 H21 0.9500 . . no
C22 H22 0.9500 . . no
C28 H28A 0.9800 . . no
C28 H28B 0.9800 . . no
C28 H28C 0.9800 . . no
C29 H29A 0.9800 . . no
C29 H29B 0.9800 . . no
C29 H29C 0.9800 . . no
C30 H30A 0.9800 . . no
C30 H30B 0.9800 . . no
C30 H30C 0.9800 . . no
C31 H31A 0.9800 . . no
C31 H31B 0.9800 . . no
C31 H31C 0.9800 . . no
C32 H32A 0.9800 . . no
C32 H32B 0.9800 . . no
C32 H32C 0.9800 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H16 Cl1 0.9500 2.7100 3.642(5) 168.00 2_646 yes
C18 H18 O1 0.9500 2.3900 2.765(6) 103.00 . yes
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
Cl1 Ir1 N1 C2 73.1(3) . . . . no
Cl1 Ir1 N1 C3 -103.7(3) . . . . no
C10 Ir1 N1 C2 -11.0(3) . . . . no
C10 Ir1 N1 C3 172.2(3) . . . . no
C23 Ir1 N1 C2 -131.3(3) . . . . no
C23 Ir1 N1 C3 52.0(3) . . . . no
C24 Ir1 N1 C2 -171.4(3) . . . . no
C24 Ir1 N1 C3 11.8(3) . . . . no
C25 Ir1 N1 C2 160.7(3) . . . . no
C25 Ir1 N1 C3 -16.1(4) . . . . no
C27 Ir1 N1 C2 -101.7(3) . . . . no
C27 Ir1 N1 C3 81.5(4) . . . . no
Cl1 Ir1 C10 C5 -77.3(3) . . . . no
Cl1 Ir1 C10 C9 95.5(4) . . . . no
N1 Ir1 C10 C5 9.1(3) . . . . no
N1 Ir1 C10 C9 -178.1(4) . . . . no
C23 Ir1 C10 C5 109.8(3) . . . . no
C23 Ir1 C10 C9 -77.4(4) . . . . no
C25 Ir1 C10 C5 -159.7(3) . . . . no
C25 Ir1 C10 C9 13.1(6) . . . . no
C26 Ir1 C10 C5 -176.7(3) . . . . no
C26 Ir1 C10 C9 -3.9(4) . . . . no
C27 Ir1 C10 C5 144.3(3) . . . . no
C27 Ir1 C10 C9 -42.9(4) . . . . no
Cl1 Ir1 C23 C24 15.1(4) . . . . no
Cl1 Ir1 C23 C27 -101.3(3) . . . . no
Cl1 Ir1 C23 C28 137.8(3) . . . . no
N1 Ir1 C23 C24 -96.5(3) . . . . no
N1 Ir1 C23 C27 147.1(2) . . . . no
N1 Ir1 C23 C28 26.2(4) . . . . no
C10 Ir1 C23 C24 178.9(3) . . . . no
C10 Ir1 C23 C27 62.4(3) . . . . no
C10 Ir1 C23 C28 -58.5(4) . . . . no
C24 Ir1 C23 C27 -116.4(3) . . . . no
C24 Ir1 C23 C28 122.7(5) . . . . no
C25 Ir1 C23 C24 35.5(3) . . . . no
C25 Ir1 C23 C27 -80.9(2) . . . . no
C25 Ir1 C23 C28 158.2(4) . . . . no
C26 Ir1 C23 C24 78.9(3) . . . . no
C26 Ir1 C23 C27 -37.5(2) . . . . no
C26 Ir1 C23 C28 -158.4(4) . . . . no
C27 Ir1 C23 C24 116.4(3) . . . . no
C27 Ir1 C23 C28 -120.9(5) . . . . no
Cl1 Ir1 C24 C23 -172.6(2) . . . . no
Cl1 Ir1 C24 C25 -53.4(3) . . . . no
Cl1 Ir1 C24 C29 69.0(4) . . . . no
N1 Ir1 C24 C23 95.0(3) . . . . no
N1 Ir1 C24 C25 -145.7(3) . . . . no
N1 Ir1 C24 C29 -23.3(4) . . . . no
C23 Ir1 C24 C25 119.2(4) . . . . no
C23 Ir1 C24 C29 -118.3(4) . . . . no
C25 Ir1 C24 C23 -119.2(4) . . . . no
C25 Ir1 C24 C29 122.4(5) . . . . no
C26 Ir1 C24 C23 -82.3(3) . . . . no
C26 Ir1 C24 C25 36.9(3) . . . . no
C26 Ir1 C24 C29 159.4(4) . . . . no
C27 Ir1 C24 C23 -38.7(3) . . . . no
C27 Ir1 C24 C25 80.5(3) . . . . no
C27 Ir1 C24 C29 -157.1(4) . . . . no
Cl1 Ir1 C25 C24 133.7(3) . . . . no
Cl1 Ir1 C25 C26 -105.6(2) . . . . no
Cl1 Ir1 C25 C30 10.2(4) . . . . no
N1 Ir1 C25 C24 49.0(3) . . . . no
N1 Ir1 C25 C26 169.6(2) . . . . no
N1 Ir1 C25 C30 -74.5(4) . . . . no
C10 Ir1 C25 C24 -146.3(3) . . . . no
C10 Ir1 C25 C26 -25.7(4) . . . . no
C10 Ir1 C25 C30 90.2(5) . . . . no
C23 Ir1 C25 C24 -37.4(3) . . . . no
C23 Ir1 C25 C26 83.2(3) . . . . no
C23 Ir1 C25 C30 -160.9(4) . . . . no
C24 Ir1 C25 C26 120.7(4) . . . . no
C24 Ir1 C25 C30 -123.5(5) . . . . no
C26 Ir1 C25 C24 -120.7(4) . . . . no
C26 Ir1 C25 C30 115.8(4) . . . . no
C27 Ir1 C25 C24 -81.2(3) . . . . no
C27 Ir1 C25 C26 39.5(2) . . . . no
C27 Ir1 C25 C30 155.4(4) . . . . no
Cl1 Ir1 C26 C25 78.8(2) . . . . no
Cl1 Ir1 C26 C27 -166.37(18) . . . . no
Cl1 Ir1 C26 C31 -41.8(4) . . . . no
C10 Ir1 C26 C25 165.7(2) . . . . no
C10 Ir1 C26 C27 -79.5(2) . . . . no
C10 Ir1 C26 C31 45.1(4) . . . . no
C23 Ir1 C26 C25 -77.4(2) . . . . no
C23 Ir1 C26 C27 37.5(2) . . . . no
C23 Ir1 C26 C31 162.0(4) . . . . no
C24 Ir1 C26 C25 -34.6(2) . . . . no
C24 Ir1 C26 C27 80.2(2) . . . . no
C24 Ir1 C26 C31 -155.3(4) . . . . no
C25 Ir1 C26 C27 114.8(3) . . . . no
C25 Ir1 C26 C31 -120.6(5) . . . . no
C27 Ir1 C26 C25 -114.8(3) . . . . no
C27 Ir1 C26 C31 124.6(4) . . . . no
Cl1 Ir1 C27 C23 138.96(19) . . . . no
Cl1 Ir1 C27 C26 20.5(3) . . . . no
Cl1 Ir1 C27 C32 -101.8(3) . . . . no
N1 Ir1 C27 C23 -48.8(3) . . . . no
N1 Ir1 C27 C26 -167.3(3) . . . . no
N1 Ir1 C27 C32 70.4(4) . . . . no
C10 Ir1 C27 C23 -130.5(2) . . . . no
C10 Ir1 C27 C26 111.1(2) . . . . no
C10 Ir1 C27 C32 -11.2(4) . . . . no
C23 Ir1 C27 C26 -118.5(3) . . . . no
C23 Ir1 C27 C32 119.3(4) . . . . no
C24 Ir1 C27 C23 38.2(2) . . . . no
C24 Ir1 C27 C26 -80.2(2) . . . . no
C24 Ir1 C27 C32 157.5(4) . . . . no
C25 Ir1 C27 C23 79.0(2) . . . . no
C25 Ir1 C27 C26 -39.4(2) . . . . no
C25 Ir1 C27 C32 -161.7(4) . . . . no
C26 Ir1 C27 C23 118.5(3) . . . . no
C26 Ir1 C27 C32 -122.3(4) . . . . no
C4 O1 C2 N1 13.1(5) . . . . no
C4 O1 C2 C5 -169.5(4) . . . . no
C2 O1 C4 C17 -153.8(4) . . . . no
C2 O1 C4 C3 -25.3(4) . . . . no
C3 N1 C2 O1 6.3(5) . . . . no
Ir1 N1 C2 O1 -171.4(3) . . . . no
C2 N1 C3 C11 99.3(4) . . . . no
Ir1 N1 C2 C5 11.2(5) . . . . no
C3 N1 C2 C5 -171.2(4) . . . . no
Ir1 N1 C3 C11 -83.8(4) . . . . no
Ir1 N1 C3 C4 155.7(2) . . . . no
C2 N1 C3 C4 -21.3(4) . . . . no
N1 C2 C5 C10 -3.2(6) . . . . no
O1 C2 C5 C6 -0.5(7) . . . . no
O1 C2 C5 C10 179.5(4) . . . . no
N1 C2 C5 C6 176.9(4) . . . . no
N1 C3 C4 O1 27.6(3) . . . . no
C11 C3 C4 C17 33.5(5) . . . . no
N1 C3 C11 C12 -39.5(6) . . . . no
N1 C3 C11 C16 139.5(5) . . . . no
C4 C3 C11 C12 71.2(6) . . . . no
C4 C3 C11 C16 -109.9(5) . . . . no
N1 C3 C4 C17 150.9(3) . . . . no
C11 C3 C4 O1 -89.8(4) . . . . no
O1 C4 C17 C18 -3.6(6) . . . . no
O1 C4 C17 C22 179.4(4) . . . . no
C3 C4 C17 C18 -123.1(5) . . . . no
C3 C4 C17 C22 59.9(5) . . . . no
C2 C5 C6 C7 -178.4(4) . . . . no
C10 C5 C6 C7 1.6(6) . . . . no
C2 C5 C10 Ir1 -6.5(5) . . . . no
C2 C5 C10 C9 179.8(4) . . . . no
C6 C5 C10 Ir1 173.5(3) . . . . no
C6 C5 C10 C9 -0.2(6) . . . . no
C5 C6 C7 C8 -1.2(6) . . . . no
C6 C7 C8 C9 -0.6(6) . . . . no
C7 C8 C9 C10 2.1(6) . . . . no
C8 C9 C10 Ir1 -174.3(3) . . . . no
C8 C9 C10 C5 -1.6(6) . . . . no
C3 C11 C12 C13 178.9(5) . . . . no
C16 C11 C12 C13 -0.1(7) . . . . no
C3 C11 C16 C15 -178.6(5) . . . . no
C12 C11 C16 C15 0.4(7) . . . . no
C11 C12 C13 C14 -0.6(7) . . . . no
C12 C13 C14 C15 1.1(8) . . . . no
C13 C14 C15 C16 -0.8(8) . . . . no
C14 C15 C16 C11 0.0(8) . . . . no
C4 C17 C18 C19 -176.3(4) . . . . no
C22 C17 C18 C19 0.7(7) . . . . no
C4 C17 C22 C21 176.7(4) . . . . no
C18 C17 C22 C21 -0.4(7) . . . . no
C17 C18 C19 C20 -0.6(7) . . . . no
C18 C19 C20 C21 0.3(7) . . . . no
C19 C20 C21 C22 0.0(7) . . . . no
C20 C21 C22 C17 0.0(7) . . . . no
Ir1 C23 C24 C25 -60.7(3) . . . . no
Ir1 C23 C24 C29 120.2(5) . . . . no
C27 C23 C24 Ir1 62.3(3) . . . . no
C27 C23 C24 C25 1.7(5) . . . . no
C27 C23 C24 C29 -177.4(4) . . . . no
C28 C23 C24 Ir1 -127.6(5) . . . . no
C28 C23 C24 C25 171.7(4) . . . . no
C28 C23 C24 C29 -7.4(8) . . . . no
Ir1 C23 C27 C26 60.8(3) . . . . no
Ir1 C23 C27 C32 -122.6(4) . . . . no
C24 C23 C27 Ir1 -64.9(3) . . . . no
C24 C23 C27 C26 -4.1(5) . . . . no
C24 C23 C27 C32 172.4(4) . . . . no
C28 C23 C27 Ir1 125.1(4) . . . . no
C28 C23 C27 C26 -174.1(4) . . . . no
C28 C23 C27 C32 2.5(7) . . . . no
Ir1 C24 C25 C26 -56.4(3) . . . . no
Ir1 C24 C25 C30 122.5(5) . . . . no
C23 C24 C25 Ir1 57.8(3) . . . . no
C23 C24 C25 C26 1.4(5) . . . . no
C23 C24 C25 C30 -179.7(4) . . . . no
C29 C24 C25 Ir1 -123.1(5) . . . . no
C29 C24 C25 C26 -179.5(5) . . . . no
C29 C24 C25 C30 -0.6(8) . . . . no
Ir1 C25 C26 C27 -63.3(3) . . . . no
Ir1 C25 C26 C31 122.3(5) . . . . no
C24 C25 C26 Ir1 59.4(3) . . . . no
C24 C25 C26 C27 -3.9(5) . . . . no
C24 C25 C26 C31 -178.3(4) . . . . no
C30 C25 C26 Ir1 -119.5(4) . . . . no
C30 C25 C26 C27 177.2(4) . . . . no
C30 C25 C26 C31 2.8(7) . . . . no
Ir1 C26 C27 C23 -61.0(3) . . . . no
Ir1 C26 C27 C32 122.5(4) . . . . no
C25 C26 C27 Ir1 65.9(3) . . . . no
C25 C26 C27 C23 4.9(5) . . . . no
C25 C26 C27 C32 -171.5(4) . . . . no
C31 C26 C27 Ir1 -120.1(5) . . . . no
C31 C26 C27 C23 178.9(4) . . . . no
C31 C26 C27 C32 2.4(7) . . . . no
