#------------------------------------------------------------------------------
#$Date: 2020-12-09 05:19:06 +0200 (Wed, 09 Dec 2020) $
#$Revision: 259697 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/58/7705888.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_7705888
loop_
_publ_author_name
'Sevim, Mehmet'
'Kavukcu, Serdar Batıkan'
'Kınal, Armağan'
'Şahin, Onur'
'Türkmen, Hayati'
_publ_section_title
;
 C-C coupling formation using nitron complexes.
;
_journal_issue                   46
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16903
_journal_page_last               16915
_journal_paper_doi               10.1039/d0dt02937h
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C20 H17 N4, C10 H15 Cl3 Ir '
_chemical_formula_sum            'C30 H32 Cl3 Ir N4'
_chemical_formula_weight         747.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-12-04 deposited with the CCDC.	2020-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                98.645(4)
_cell_angle_beta                 96.039(5)
_cell_angle_gamma                110.163(4)
_cell_formula_units_Z            2
_cell_length_a                   9.9976(9)
_cell_length_b                   11.8767(12)
_cell_length_c                   13.6237(14)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.89
_cell_volume                     1479.6(3)
_computing_cell_refinement       'SAINT(Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.983
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39096
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.417
_diffrn_reflns_theta_min         2.889
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.809
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.109
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5978
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0576
_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)+12.3920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4972
_reflns_number_total             5978
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt02937h2.cif
_cod_data_source_block           shelx_CCDC2
_cod_database_code               7705888
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.9456(9) 0.7036(8) 0.9406(6) 0.037(2) Uani 1 1 d . . . . .
C2 C 1.0028(9) 0.6139(8) 0.9021(6) 0.0338(19) Uani 1 1 d . . . . .
C3 C 0.8837(9) 0.4985(8) 0.8633(6) 0.036(2) Uani 1 1 d . . . . .
C4 C 0.7525(9) 0.5190(9) 0.8799(6) 0.040(2) Uani 1 1 d . . . . .
C5 C 0.7897(10) 0.6450(9) 0.9252(6) 0.038(2) Uani 1 1 d . . . . .
C6 C 1.0306(12) 0.8336(9) 0.9890(8) 0.060(3) Uani 1 1 d . . . . .
H6A H 0.9660 0.8738 1.0078 0.090 Uiso 1 1 calc R U . . .
H6B H 1.0861 0.8740 0.9425 0.090 Uiso 1 1 calc R U . . .
H6C H 1.0946 0.8369 1.0480 0.090 Uiso 1 1 calc R U . . .
C7 C 1.1578(9) 0.6316(10) 0.9048(7) 0.054(3) Uani 1 1 d . . . . .
H7A H 1.1656 0.5565 0.8739 0.082 Uiso 1 1 calc R U . . .
H7B H 1.2064 0.6552 0.9735 0.082 Uiso 1 1 calc R U . . .
H7C H 1.2015 0.6946 0.8688 0.082 Uiso 1 1 calc R U . . .
C8 C 0.8953(13) 0.3802(9) 0.8186(8) 0.059(3) Uani 1 1 d . . . . .
H8A H 0.9949 0.3925 0.8163 0.089 Uiso 1 1 calc R U . . .
H8B H 0.8407 0.3513 0.7515 0.089 Uiso 1 1 calc R U . . .
H8C H 0.8578 0.3209 0.8591 0.089 Uiso 1 1 calc R U . . .
C9 C 0.6035(10) 0.4235(11) 0.8525(9) 0.069(3) Uani 1 1 d . . . . .
H9A H 0.6086 0.3467 0.8232 0.104 Uiso 1 1 calc R U . . .
H9B H 0.5460 0.4474 0.8049 0.104 Uiso 1 1 calc R U . . .
H9C H 0.5602 0.4151 0.9120 0.104 Uiso 1 1 calc R U . . .
C10 C 0.6878(12) 0.7024(11) 0.9612(8) 0.065(3) Uani 1 1 d . . . . .
H10A H 0.7400 0.7879 0.9886 0.097 Uiso 1 1 calc R U . . .
H10B H 0.6434 0.6631 1.0124 0.097 Uiso 1 1 calc R U . . .
H10C H 0.6146 0.6932 0.9059 0.097 Uiso 1 1 calc R U . . .
C11 C 0.2668(9) 0.5274(7) 0.5610(6) 0.0334(19) Uani 1 1 d . . . . .
H11 H 0.2119 0.4914 0.4973 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4074(9) 0.7292(7) 0.5253(6) 0.038(2) Uani 1 1 d . . . . .
C13 C 0.3044(11) 0.7616(9) 0.4747(8) 0.054(3) Uani 1 1 d . . . . .
H13 H 0.2086 0.7306 0.4839 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3466(14) 0.8420(10) 0.4094(8) 0.067(3) Uani 1 1 d . . . . .
H14 H 0.2789 0.8655 0.3745 0.081 Uiso 1 1 calc R U . . .
C15 C 0.4871(14) 0.8858(9) 0.3968(8) 0.066(3) Uani 1 1 d . . . . .
H15 H 0.5154 0.9399 0.3535 0.079 Uiso 1 1 calc R U . . .
C16 C 0.5879(13) 0.8509(10) 0.4476(9) 0.070(3) Uani 1 1 d . . . . .
H16 H 0.6834 0.8809 0.4376 0.084 Uiso 1 1 calc R U . . .
C17 C 0.5489(11) 0.7720(9) 0.5131(8) 0.054(3) Uani 1 1 d . . . . .
H17 H 0.6168 0.7486 0.5480 0.065 Uiso 1 1 calc R U . . .
C18 C 0.4162(8) 0.6566(7) 0.6901(6) 0.0304(18) Uani 1 1 d . . . . .
C19 C 0.4879(9) 0.8654(7) 0.7827(6) 0.0344(19) Uani 1 1 d . . . . .
C20 C 0.3481(9) 0.8624(8) 0.7673(7) 0.041(2) Uani 1 1 d . . . . .
H20 H 0.2735 0.7925 0.7307 0.049 Uiso 1 1 calc R U . . .
C21 C 0.3200(12) 0.9644(9) 0.8070(9) 0.060(3) Uani 1 1 d . . . . .
H21 H 0.2257 0.9625 0.7976 0.072 Uiso 1 1 calc R U . . .
C22 C 0.4298(14) 1.0686(10) 0.8601(9) 0.070(3) Uani 1 1 d . . . . .
H22 H 0.4105 1.1371 0.8868 0.084 Uiso 1 1 calc R U . . .
C23 C 0.5675(13) 1.0699(10) 0.8729(9) 0.072(3) Uani 1 1 d . . . . .
H23 H 0.6420 1.1404 0.9087 0.086 Uiso 1 1 calc R U . . .
C24 C 0.5996(11) 0.9701(9) 0.8346(8) 0.055(3) Uani 1 1 d . . . . .
H24 H 0.6943 0.9730 0.8435 0.066 Uiso 1 1 calc R U . . .
C25 C 0.1838(8) 0.3507(7) 0.6441(6) 0.0308(18) Uani 1 1 d . . . . .
C26 C 0.1971(10) 0.3117(9) 0.7332(7) 0.045(2) Uani 1 1 d . . . . .
H26 H 0.2566 0.3648 0.7910 0.054 Uiso 1 1 calc R U . . .
C27 C 0.1189(12) 0.1902(10) 0.7340(9) 0.059(3) Uani 1 1 d . . . . .
H27 H 0.1290 0.1611 0.7929 0.071 Uiso 1 1 calc R U . . .
C28 C 0.0283(13) 0.1128(10) 0.6515(10) 0.068(3) Uani 1 1 d . . . . .
H28 H -0.0259 0.0324 0.6542 0.082 Uiso 1 1 calc R U . . .
C29 C 0.0178(13) 0.1553(9) 0.5637(9) 0.069(3) Uani 1 1 d . . . . .
H29 H -0.0439 0.1024 0.5067 0.083 Uiso 1 1 calc R U . . .
C30 C 0.0962(11) 0.2741(9) 0.5579(8) 0.057(3) Uani 1 1 d . . . . .
H30 H 0.0900 0.3015 0.4977 0.068 Uiso 1 1 calc R U . . .
Cl1 Cl 1.0040(2) 0.6035(2) 0.65481(15) 0.0402(5) Uani 1 1 d . . . . .
Cl2 Cl 0.8843(3) 0.8318(2) 0.7454(2) 0.0522(6) Uani 1 1 d . . . . .
Cl3 Cl 0.6543(2) 0.5505(2) 0.64934(17) 0.0428(5) Uani 1 1 d . . . . .
Ir1 Ir 0.85994(3) 0.63386(3) 0.78229(2) 0.02596(10) Uani 1 1 d . . . . .
N1 N 0.3632(7) 0.6417(6) 0.5899(5) 0.0288(14) Uani 1 1 d . . . . .
N2 N 0.2645(6) 0.4756(5) 0.6397(5) 0.0265(14) Uani 1 1 d . . . . .
N3 N 0.3561(7) 0.5554(6) 0.7229(5) 0.0315(15) Uani 1 1 d . . . . .
N4 N 0.5198(8) 0.7610(7) 0.7474(6) 0.0383(17) Uani 1 1 d D . . . .
H4A H 0.608(4) 0.772(10) 0.742(8) 0.07(4) Uiso 1 1 d D . . . .
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
C2 C1 C5 107.9(7) . . ?
C2 C1 C6 126.3(8) . . ?
C5 C1 C6 125.8(8) . . ?
C2 C1 Ir1 70.3(4) . . ?
C5 C1 Ir1 69.6(5) . . ?
C6 C1 Ir1 126.2(6) . . ?
C1 C2 C3 108.6(7) . . ?
C1 C2 C7 126.8(8) . . ?
C3 C2 C7 124.5(8) . . ?
C1 C2 Ir1 70.9(4) . . ?
C3 C2 Ir1 70.1(4) . . ?
C7 C2 Ir1 127.0(6) . . ?
C4 C3 C2 106.9(8) . . ?
C4 C3 C8 126.7(9) . . ?
C2 C3 C8 126.3(8) . . ?
C4 C3 Ir1 70.4(4) . . ?
C2 C3 Ir1 70.5(4) . . ?
C8 C3 Ir1 126.0(6) . . ?
C5 C4 C3 108.7(8) . . ?
C5 C4 C9 126.3(9) . . ?
C3 C4 C9 125.0(9) . . ?
C5 C4 Ir1 70.1(5) . . ?
C3 C4 Ir1 70.1(4) . . ?
C9 C4 Ir1 125.1(6) . . ?
C4 C5 C1 107.9(7) . . ?
C4 C5 C10 126.0(9) . . ?
C1 C5 C10 125.7(9) . . ?
C4 C5 Ir1 70.9(5) . . ?
C1 C5 Ir1 71.0(5) . . ?
C10 C5 Ir1 129.0(6) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 N1 106.9(7) . . ?
N2 C11 H11 126.5 . . ?
N1 C11 H11 126.5 . . ?
C17 C12 C13 122.5(9) . . ?
C17 C12 N1 118.6(8) . . ?
C13 C12 N1 118.8(8) . . ?
C12 C13 C14 118.5(10) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C15 C14 C13 119.7(11) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.6(10) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 120.8(11) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 117.9(10) . . ?
C12 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
N3 C18 N4 124.6(8) . . ?
N3 C18 N1 110.5(7) . . ?
N4 C18 N1 124.9(7) . . ?
C20 C19 C24 120.6(8) . . ?
C20 C19 N4 120.9(8) . . ?
C24 C19 N4 118.5(8) . . ?
C19 C20 C21 119.2(9) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 120.8(10) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 118.8(10) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C24 122.1(10) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C19 118.4(10) . . ?
C23 C24 H24 120.8 . . ?
C19 C24 H24 120.8 . . ?
C26 C25 C30 122.3(8) . . ?
C26 C25 N2 119.4(8) . . ?
C30 C25 N2 118.3(7) . . ?
C25 C26 C27 117.6(9) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C28 C27 C26 121.9(10) . . ?
C28 C27 H27 119.0 . . ?
C26 C27 H27 119.0 . . ?
C27 C28 C29 118.7(10) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C28 C29 C30 121.8(10) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C25 C30 C29 117.6(9) . . ?
C25 C30 H30 121.2 . . ?
C29 C30 H30 121.2 . . ?
C5 Ir1 C3 66.2(3) . . ?
C5 Ir1 C4 39.0(3) . . ?
C3 Ir1 C4 39.4(3) . . ?
C5 Ir1 C2 65.8(3) . . ?
C3 Ir1 C2 39.4(3) . . ?
C4 Ir1 C2 65.6(3) . . ?
C5 Ir1 C1 39.4(3) . . ?
C3 Ir1 C1 65.9(3) . . ?
C4 Ir1 C1 65.4(3) . . ?
C2 Ir1 C1 38.9(3) . . ?
C5 Ir1 Cl3 109.9(3) . . ?
C3 Ir1 Cl3 112.2(2) . . ?
C4 Ir1 Cl3 93.0(2) . . ?
C2 Ir1 Cl3 151.5(2) . . ?
C1 Ir1 Cl3 148.8(2) . . ?
C5 Ir1 Cl2 101.7(2) . . ?
C3 Ir1 Cl2 159.9(2) . . ?
C4 Ir1 Cl2 137.4(3) . . ?
C2 Ir1 Cl2 121.7(2) . . ?
C1 Ir1 Cl2 94.4(2) . . ?
Cl3 Ir1 Cl2 86.70(8) . . ?
C5 Ir1 Cl1 159.6(2) . . ?
C3 Ir1 Cl1 97.1(2) . . ?
C4 Ir1 Cl1 132.1(3) . . ?
C2 Ir1 Cl1 93.9(2) . . ?
C1 Ir1 Cl1 124.2(2) . . ?
Cl3 Ir1 Cl1 86.87(7) . . ?
Cl2 Ir1 Cl1 90.54(9) . . ?
C11 N1 C18 106.9(7) . . ?
C11 N1 C12 125.7(7) . . ?
C18 N1 C12 127.3(7) . . ?
C11 N2 N3 111.6(6) . . ?
C11 N2 C25 127.5(7) . . ?
N3 N2 C25 120.8(6) . . ?
C18 N3 N2 104.1(6) . . ?
C18 N4 C19 121.6(7) . . ?
C18 N4 H4A 117(8) . . ?
C19 N4 H4A 117(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
C1 C2 1.433(11) . ?
C1 C5 1.448(12) . ?
C1 C6 1.487(13) . ?
C1 Ir1 2.158(8) . ?
C2 C3 1.449(12) . ?
C2 C7 1.486(11) . ?
C2 Ir1 2.150(7) . ?
C3 C4 1.448(11) . ?
C3 C8 1.492(12) . ?
C3 Ir1 2.145(8) . ?
C4 C5 1.432(13) . ?
C4 C9 1.495(13) . ?
C4 Ir1 2.149(8) . ?
C5 C10 1.493(12) . ?
C5 Ir1 2.139(8) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.312(10) . ?
C11 N1 1.335(10) . ?
C11 H11 0.9300 . ?
C12 C17 1.366(12) . ?
C12 C13 1.374(12) . ?
C12 N1 1.446(10) . ?
C13 C14 1.391(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(16) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(14) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N3 1.313(10) . ?
C18 N4 1.369(10) . ?
C18 N1 1.374(10) . ?
C19 C20 1.379(12) . ?
C19 C24 1.380(12) . ?
C19 N4 1.413(11) . ?
C20 C21 1.381(13) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(15) . ?
C21 H21 0.9300 . ?
C22 C23 1.364(16) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(15) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.373(11) . ?
C25 C30 1.374(12) . ?
C25 N2 1.438(9) . ?
C26 C27 1.386(13) . ?
C26 H26 0.9300 . ?
C27 C28 1.352(16) . ?
C27 H27 0.9300 . ?
C28 C29 1.374(15) . ?
C28 H28 0.9300 . ?
C29 C30 1.377(13) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
Cl1 Ir1 2.433(2) . ?
Cl2 Ir1 2.413(2) . ?
Cl3 Ir1 2.400(2) . ?
N2 N3 1.371(9) . ?
N4 H4A 0.85(2) . ?
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
C11 H11 Cl1 0.93 2.63 3.528(8) 163.2 2_666
C11 H11 Cl3 0.93 2.60 3.142(9) 117.8 2_666
C20 H20 Cl1 0.93 2.81 3.717(9) 164.5 1_455
C30 H30 Cl1 0.93 2.74 3.629(10) 160.7 2_666
N4 H4A Cl2 0.85(2) 2.60(3) 3.450(8) 172(10) .
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
C5 C1 C2 C3 -0.5(9) . . . . ?
C6 C1 C2 C3 178.7(8) . . . . ?
Ir1 C1 C2 C3 -60.2(5) . . . . ?
C5 C1 C2 C7 -177.8(8) . . . . ?
C6 C1 C2 C7 1.4(14) . . . . ?
Ir1 C1 C2 C7 122.5(8) . . . . ?
C5 C1 C2 Ir1 59.7(5) . . . . ?
C6 C1 C2 Ir1 -121.1(9) . . . . ?
C1 C2 C3 C4 -0.7(9) . . . . ?
C7 C2 C3 C4 176.7(7) . . . . ?
Ir1 C2 C3 C4 -61.4(5) . . . . ?
C1 C2 C3 C8 -178.5(8) . . . . ?
C7 C2 C3 C8 -1.1(13) . . . . ?
Ir1 C2 C3 C8 120.8(9) . . . . ?
C1 C2 C3 Ir1 60.7(5) . . . . ?
C7 C2 C3 Ir1 -121.9(8) . . . . ?
C2 C3 C4 C5 1.6(9) . . . . ?
C8 C3 C4 C5 179.4(8) . . . . ?
Ir1 C3 C4 C5 -59.7(5) . . . . ?
C2 C3 C4 C9 -179.1(8) . . . . ?
C8 C3 C4 C9 -1.3(14) . . . . ?
Ir1 C3 C4 C9 119.6(9) . . . . ?
C2 C3 C4 Ir1 61.4(5) . . . . ?
C8 C3 C4 Ir1 -120.8(9) . . . . ?
C3 C4 C5 C1 -1.9(9) . . . . ?
C9 C4 C5 C1 178.8(8) . . . . ?
Ir1 C4 C5 C1 -61.7(5) . . . . ?
C3 C4 C5 C10 -175.4(8) . . . . ?
C9 C4 C5 C10 5.3(14) . . . . ?
Ir1 C4 C5 C10 124.8(8) . . . . ?
C3 C4 C5 Ir1 59.8(5) . . . . ?
C9 C4 C5 Ir1 -119.5(9) . . . . ?
C2 C1 C5 C4 1.5(9) . . . . ?
C6 C1 C5 C4 -177.7(8) . . . . ?
Ir1 C1 C5 C4 61.6(5) . . . . ?
C2 C1 C5 C10 175.0(8) . . . . ?
C6 C1 C5 C10 -4.2(13) . . . . ?
Ir1 C1 C5 C10 -124.9(8) . . . . ?
C2 C1 C5 Ir1 -60.1(5) . . . . ?
C6 C1 C5 Ir1 120.6(9) . . . . ?
C17 C12 C13 C14 -0.6(16) . . . . ?
N1 C12 C13 C14 -177.3(9) . . . . ?
C12 C13 C14 C15 0.3(17) . . . . ?
C13 C14 C15 C16 0.4(18) . . . . ?
C14 C15 C16 C17 -0.8(18) . . . . ?
C13 C12 C17 C16 0.2(16) . . . . ?
N1 C12 C17 C16 177.0(9) . . . . ?
C15 C16 C17 C12 0.4(17) . . . . ?
C24 C19 C20 C21 -1.8(14) . . . . ?
N4 C19 C20 C21 177.0(9) . . . . ?
C19 C20 C21 C22 0.9(16) . . . . ?
C20 C21 C22 C23 0.1(18) . . . . ?
C21 C22 C23 C24 0(2) . . . . ?
C22 C23 C24 C19 -0.7(19) . . . . ?
C20 C19 C24 C23 1.7(15) . . . . ?
N4 C19 C24 C23 -177.1(10) . . . . ?
C30 C25 C26 C27 0.3(14) . . . . ?
N2 C25 C26 C27 -179.2(8) . . . . ?
C25 C26 C27 C28 -2.3(16) . . . . ?
C26 C27 C28 C29 2.3(18) . . . . ?
C27 C28 C29 C30 -0.4(19) . . . . ?
C26 C25 C30 C29 1.5(15) . . . . ?
N2 C25 C30 C29 -178.9(9) . . . . ?
C28 C29 C30 C25 -1.5(18) . . . . ?
N2 C11 N1 C18 -1.2(9) . . . . ?
N2 C11 N1 C12 175.7(7) . . . . ?
N3 C18 N1 C11 0.4(9) . . . . ?
N4 C18 N1 C11 178.7(8) . . . . ?
N3 C18 N1 C12 -176.5(7) . . . . ?
N4 C18 N1 C12 1.8(12) . . . . ?
C17 C12 N1 C11 -117.9(10) . . . . ?
C13 C12 N1 C11 59.0(12) . . . . ?
C17 C12 N1 C18 58.4(12) . . . . ?
C13 C12 N1 C18 -124.7(9) . . . . ?
N1 C11 N2 N3 1.7(9) . . . . ?
N1 C11 N2 C25 -176.0(7) . . . . ?
C26 C25 N2 C11 178.6(8) . . . . ?
C30 C25 N2 C11 -1.0(12) . . . . ?
C26 C25 N2 N3 1.1(11) . . . . ?
C30 C25 N2 N3 -178.5(8) . . . . ?
N4 C18 N3 N2 -177.8(7) . . . . ?
N1 C18 N3 N2 0.6(8) . . . . ?
C11 N2 N3 C18 -1.4(8) . . . . ?
C25 N2 N3 C18 176.5(6) . . . . ?
N3 C18 N4 C19 -106.0(10) . . . . ?
N1 C18 N4 C19 75.9(11) . . . . ?
C20 C19 N4 C18 5.2(13) . . . . ?
C24 C19 N4 C18 -176.0(9) . . . . ?
