#------------------------------------------------------------------------------
#$Date: 2025-12-04 01:06:08 +0100 (Thu 04 de Dec de 2025) $
#$Revision: 304022 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/99/7719971.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_7719971
loop_
_publ_author_name
'Fernández-Moreira, Vanesa'
'Morales-Pioz, Eva'
'Martínez-Estévez, Mónica'
'Benedí Visiedo, Andrea'
'Tejera-Ruiz, María'
'Marzo, Isabel'
'Gimeno, M. Concepción'
'Vazquez-Lopez, Ezequiel M.'
'García-Fontán, Soledad'
_publ_section_title
;
 Structure--activity insights into Benzimidazole-based Ir(III)
 cyclometallated complexes for cancer therapy
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D5DT02366A
_journal_year                    2025
_chemical_formula_sum            'C57.7 H50.4 Cl4.4 Ir N7 O4'
_chemical_formula_weight         1254.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-09-30 deposited with the CCDC.	2025-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.818(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.908(3)
_cell_length_b                   16.4721(15)
_cell_length_c                   30.381(3)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.62
_cell_volume                     11325(2)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0767
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            98980
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.273
_exptl_absorpt_coefficient_mu    2.617
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       needle
_exptl_crystal_F_000             5035
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         6.624
_refine_diff_density_min         -2.211
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         9939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0788
_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)+(0.0803P)²+241.8648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.2028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8302
_reflns_number_total             9939
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt02366a2.cif
_cod_data_source_block           mo_con113v_0ms
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C57.70 H50.40 Cl4.40 Ir N7 O4'
_cod_database_code               7719971
_shelx_shelxl_version_number     2018/3
_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. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.28678(2) 0.48188(2) 0.06307(2) 0.05189(17) Uani 1 1 d . . . . .
Cl1 Cl 0.39728(14) 0.6864(2) 0.27118(10) 0.0752(8) Uani 1 1 d . . . . .
O11 O 0.0618(4) 0.3797(8) -0.0021(3) 0.104(4) Uani 1 1 d . . . . .
O12 O 0.1991(11) 0.5257(9) -0.2448(4) 0.179(9) Uani 1 1 d . . . . .
N11 N 0.2858(5) 0.5851(5) 0.0245(3) 0.063(3) Uani 1 1 d . . . . .
N12 N 0.2414(6) 0.6595(7) -0.0380(4) 0.083(3) Uani 1 1 d . . . . .
C111 C 0.2360(6) 0.5959(7) -0.0111(4) 0.070(3) Uani 1 1 d . . . . .
C112 C 0.2979(8) 0.6891(8) -0.0183(5) 0.083(4) Uani 1 1 d . . . . .
C113 C 0.3249(6) 0.6420(7) 0.0203(4) 0.071(3) Uani 1 1 d . . . . .
C114 C 0.3837(7) 0.6575(8) 0.0469(5) 0.086(4) Uani 1 1 d . . . . .
H114 H 0.403627 0.624168 0.072704 0.103 Uiso 1 1 calc R U . . .
C115 C 0.4116(8) 0.7223(10) 0.0345(7) 0.111(6) Uani 1 1 d . . . . .
H115 H 0.451098 0.734489 0.052857 0.133 Uiso 1 1 calc R U . . .
C116 C 0.3845(12) 0.7698(11) -0.0034(9) 0.140(10) Uani 1 1 d . . . . .
H116 H 0.405466 0.813975 -0.010786 0.168 Uiso 1 1 calc R U . . .
C117 C 0.3272(11) 0.7545(9) -0.0311(7) 0.120(8) Uani 1 1 d . . . . .
H117 H 0.308349 0.786771 -0.057645 0.144 Uiso 1 1 calc R U . . .
C118 C 0.1857(6) 0.5416(7) -0.0150(4) 0.065(3) Uani 1 1 d . . . . .
C119 C 0.2034(5) 0.4800(6) 0.0207(3) 0.051(2) Uani 1 1 d . . . . .
C120 C 0.1576(5) 0.4297(7) 0.0229(4) 0.060(3) Uani 1 1 d . . . . .
H120 H 0.165487 0.389794 0.046738 0.072 Uiso 1 1 calc R U . . .
C121 C 0.1013(6) 0.4357(9) -0.0081(4) 0.075(3) Uani 1 1 d . . . . .
C122 C 0.0864(7) 0.4950(11) -0.0417(5) 0.093(4) Uani 1 1 d . . . . .
H122 H 0.046976 0.500210 -0.062043 0.111 Uiso 1 1 calc R U . . .
C123 C 0.1300(8) 0.5468(10) -0.0452(4) 0.093(5) Uani 1 1 d . . . . .
H123 H 0.120969 0.586523 -0.069182 0.111 Uiso 1 1 calc R U . . .
C125 C 0.2001(9) 0.6910(9) -0.0818(5) 0.110(6) Uani 1 1 d . . . . .
H12A H 0.211287 0.747529 -0.086212 0.132 Uiso 1 1 calc R U . . .
H12B H 0.159873 0.692175 -0.079257 0.132 Uiso 1 1 calc R U . . .
C126 C 0.1986(7) 0.6418(8) -0.1243(4) 0.085(4) Uani 1 1 d G . . . .
C127 C 0.2465(6) 0.5935(8) -0.1238(3) 0.095(5) Uani 1 1 d G . . . .
H127 H 0.279077 0.588177 -0.096037 0.114 Uiso 1 1 calc R U . . .
C128 C 0.2467(8) 0.5530(9) -0.1639(5) 0.109(6) Uani 1 1 d G . . . .
H128 H 0.279190 0.519228 -0.162995 0.131 Uiso 1 1 calc R U . . .
C129 C 0.2020(14) 0.5608(11) -0.2036(6) 0.134(9) Uani 1 1 d . . . . .
C130 C 0.1546(12) 0.6109(13) -0.2035(7) 0.138(8) Uani 1 1 d . . . . .
H130 H 0.122886 0.617927 -0.231708 0.165 Uiso 1 1 calc R U . . .
C131 C 0.1524(9) 0.6500(10) -0.1645(6) 0.111(6) Uani 1 1 d . . . . .
H131 H 0.119193 0.682318 -0.165298 0.133 Uiso 1 1 calc R U . . .
C141 C 0.0055(7) 0.3803(15) -0.0343(6) 0.136(8) Uani 1 1 d . . . . .
H14A H -0.018450 0.337909 -0.026448 0.205 Uiso 1 1 calc R U . . .
H14B H -0.012800 0.433352 -0.033913 0.205 Uiso 1 1 calc R U . . .
H14C H 0.007987 0.369919 -0.065407 0.205 Uiso 1 1 calc R U . . .
C142 C 0.2459(19) 0.4813(11) -0.2462(8) 0.23(2) Uani 1 1 d . . . . .
H14D H 0.238241 0.459481 -0.277652 0.338 Uiso 1 1 calc R U . . .
H14E H 0.281182 0.515785 -0.238121 0.338 Uiso 1 1 calc R U . . .
H14F H 0.252348 0.436377 -0.223998 0.338 Uiso 1 1 calc R U . . .
O21 O 0.3613(3) 0.4144(5) -0.0827(2) 0.066(2) Uani 1 1 d . . . . .
N21 N 0.2819(4) 0.3705(5) 0.0908(2) 0.0497(19) Uani 1 1 d . . . . .
N22 N 0.2964(4) 0.2379(5) 0.0925(3) 0.0507(19) Uani 1 1 d . . . . .
C211 C 0.2994(5) 0.3086(6) 0.0712(3) 0.053(2) Uani 1 1 d . . . . .
C212 C 0.2743(4) 0.2553(6) 0.1283(3) 0.048(2) Uani 1 1 d . . . . .
C213 C 0.2644(4) 0.3392(6) 0.1270(3) 0.050(2) Uani 1 1 d . . . . .
C214 C 0.2400(5) 0.3748(7) 0.1575(3) 0.056(3) Uani 1 1 d . . . . .
H214 H 0.233228 0.431654 0.157061 0.068 Uiso 1 1 calc R U . . .
C215 C 0.2255(5) 0.3253(7) 0.1888(3) 0.061(3) Uani 1 1 d . . . . .
H215 H 0.208071 0.348402 0.209897 0.073 Uiso 1 1 calc R U . . .
C216 C 0.2360(5) 0.2424(7) 0.1902(4) 0.063(3) Uani 1 1 d . . . . .
H216 H 0.225599 0.210080 0.212257 0.076 Uiso 1 1 calc R U . . .
C217 C 0.2609(5) 0.2059(6) 0.1607(3) 0.056(3) Uani 1 1 d . . . . .
H217 H 0.268733 0.149228 0.162211 0.068 Uiso 1 1 calc R U . . .
C218 C 0.3182(5) 0.3279(6) 0.0303(3) 0.052(2) Uani 1 1 d . . . . .
C219 C 0.3105(4) 0.4105(6) 0.0185(3) 0.051(2) Uani 1 1 d . . . . .
C220 C 0.3261(5) 0.4362(7) -0.0202(3) 0.054(2) Uani 1 1 d . . . . .
H220 H 0.321639 0.491640 -0.029231 0.065 Uiso 1 1 calc R U . . .
C221 C 0.3480(5) 0.3809(7) -0.0456(3) 0.059(3) Uani 1 1 d . . . . .
C222 C 0.3565(5) 0.3016(7) -0.0329(4) 0.065(3) Uani 1 1 d . . . . .
H222 H 0.372288 0.264982 -0.050070 0.079 Uiso 1 1 calc R U . . .
C223 C 0.3419(5) 0.2743(7) 0.0057(4) 0.062(3) Uani 1 1 d . . . . .
H223 H 0.348089 0.219043 0.014967 0.075 Uiso 1 1 calc R U . . .
C240 C 0.5833(10) 0.104(2) 0.2289(10) 0.25(2) Uani 1 1 d . . . . .
H24A H 0.624842 0.116516 0.245496 0.300 Uiso 0.496(10) 1 calc R U P A 1
H24B H 0.562400 0.094874 0.251412 0.300 Uiso 0.496(10) 1 calc R U P A 1
H24C H 0.580877 0.054937 0.210097 0.300 Uiso 0.496(10) 1 calc R U P A 1
H24D H 0.617436 0.078117 0.251620 0.300 Uiso 0.504(10) 1 calc R U P A 2
H24E H 0.594668 0.123987 0.202613 0.300 Uiso 0.504(10) 1 calc R U P A 2
H24F H 0.569779 0.149497 0.243620 0.300 Uiso 0.504(10) 1 calc R U P A 2
C25 C 0.3191(6) 0.1554(8) 0.0872(4) 0.0737(17) Uani 1 1 d . . . . .
H25A H 0.315219 0.144101 0.054290 0.088 Uiso 0.496(10) 1 calc R U P A 1
H25B H 0.297938 0.112871 0.098558 0.088 Uiso 0.496(10) 1 calc R U P A 1
H25C H 0.289014 0.115603 0.089195 0.088 Uiso 0.504(10) 1 calc R U P A 2
H25D H 0.321404 0.151701 0.055254 0.088 Uiso 0.504(10) 1 calc R U P A 2
C26X C 0.3860(7) 0.1604(11) 0.1182(6) 0.0737(17) Uani 0.496(10) 1 d G . P A 1
C27X C 0.4246(7) 0.2213(11) 0.1151(6) 0.0737(17) Uani 0.496(10) 1 d G . P A 1
H27X H 0.411132 0.263693 0.092975 0.088 Uiso 0.496(10) 1 calc R U P A 1
C28X C 0.4828(7) 0.2203(10) 0.1442(5) 0.0737(17) Uani 0.496(10) 1 d G . P A 1
H28X H 0.509204 0.262021 0.141999 0.088 Uiso 0.496(10) 1 calc R U P A 1
C29X C 0.5024(7) 0.1584(11) 0.1765(6) 0.0737(17) Uani 0.496(10) 1 d G . P A 1
C30X C 0.4638(7) 0.0974(11) 0.1796(6) 0.0737(17) Uani 0.496(10) 1 d G . P A 1
H30X H 0.477257 0.054973 0.201667 0.088 Uiso 0.496(10) 1 calc R U P A 1
C31X C 0.4056(7) 0.0984(11) 0.1505(6) 0.0737(17) Uani 0.496(10) 1 d G . P A 1
H31X H 0.379149 0.056762 0.152697 0.088 Uiso 0.496(10) 1 calc R U P A 1
O22X O 0.5591(8) 0.1644(18) 0.2020(6) 0.118(10) Uani 0.496(10) 1 d . . P A 1
C26Y C 0.3768(7) 0.1284(11) 0.1196(6) 0.0737(17) Uani 0.504(10) 1 d G . P A 2
C27Y C 0.4246(7) 0.1799(10) 0.1299(5) 0.0737(17) Uani 0.504(10) 1 d G . P A 2
H27Y H 0.420333 0.232609 0.116466 0.088 Uiso 0.504(10) 1 calc R U P A 2
C28Y C 0.4785(7) 0.1552(10) 0.1596(5) 0.0737(17) Uani 0.504(10) 1 d G . P A 2
H28Y H 0.511458 0.190791 0.166775 0.088 Uiso 0.504(10) 1 calc R U P A 2
C29Y C 0.4846(7) 0.0790(10) 0.1790(6) 0.0737(17) Uani 0.504(10) 1 d G . P A 2
C30Y C 0.4369(7) 0.0274(10) 0.1687(5) 0.0737(17) Uani 0.504(10) 1 d G . P A 2
H30Y H 0.441168 -0.025256 0.182108 0.088 Uiso 0.504(10) 1 calc R U P A 2
C31Y C 0.3830(7) 0.0521(10) 0.1390(5) 0.0737(17) Uani 0.504(10) 1 d G . P A 2
H31Y H 0.350010 0.016499 0.131851 0.088 Uiso 0.504(10) 1 calc R U P A 2
O22Y O 0.5388(12) 0.0487(18) 0.2134(9) 0.133(10) Uani 0.504(10) 1 d . . P A 2
C241 C 0.3885(6) 0.3627(9) -0.1068(4) 0.075(3) Uani 1 1 d . . . . .
H24G H 0.395808 0.392827 -0.132271 0.113 Uiso 1 1 calc R U . . .
H24H H 0.426158 0.342960 -0.085419 0.113 Uiso 1 1 calc R U . . .
H24I H 0.362555 0.316472 -0.119562 0.113 Uiso 1 1 calc R U . . .
N31 N 0.2753(4) 0.5573(5) 0.1170(3) 0.055(2) Uani 1 1 d . . . . .
N32 N 0.3164(4) 0.6427(5) 0.1746(3) 0.057(2) Uani 1 1 d . . . . .
H32 H 0.343951 0.668951 0.196231 0.068 Uiso 1 1 calc R U . . .
H3N H 0.343951 0.668951 0.196231 0.068 Uiso 1 1 calc R U . . .
N33 N 0.3767(4) 0.4975(5) 0.1112(3) 0.055(2) Uani 1 1 d . . . . .
C311 C 0.3263(5) 0.5837(6) 0.1467(3) 0.049(2) Uani 1 1 d . . . . .
C312 C 0.2582(5) 0.6548(6) 0.1640(3) 0.056(3) Uani 1 1 d . . . . .
C313 C 0.2316(6) 0.5988(7) 0.1273(4) 0.065(3) Uani 1 1 d . . . . .
C314 C 0.1705(5) 0.5926(8) 0.1076(4) 0.067(3) Uani 1 1 d . . . . .
H314 H 0.151646 0.555523 0.083475 0.081 Uiso 1 1 calc R U . . .
C315 C 0.1400(6) 0.6462(9) 0.1269(4) 0.077(4) Uani 1 1 d . . . . .
H315 H 0.098058 0.644794 0.115023 0.093 Uiso 1 1 calc R U . . .
C316 C 0.1659(7) 0.7019(10) 0.1623(5) 0.087(4) Uani 1 1 d . . . . .
H316 H 0.141751 0.735700 0.174053 0.105 Uiso 1 1 calc R U . . .
C317 C 0.2237(6) 0.7074(8) 0.1793(4) 0.074(3) Uani 1 1 d . . . . .
H317 H 0.241556 0.747369 0.201994 0.089 Uiso 1 1 calc R U . . .
C318 C 0.3822(5) 0.5525(7) 0.1457(4) 0.062(3) Uani 1 1 d . . . . .
C319 C 0.4353(5) 0.5746(7) 0.1749(4) 0.068(3) Uani 1 1 d . . . . .
H319 H 0.437415 0.612993 0.198740 0.082 Uiso 1 1 calc R U . . .
C320 C 0.4866(6) 0.5427(9) 0.1711(5) 0.090(4) Uani 1 1 d . . . . .
H320 H 0.524194 0.559286 0.191207 0.108 Uiso 1 1 calc R U . . .
C321 C 0.4812(6) 0.4849(9) 0.1365(6) 0.089(4) Uani 1 1 d . . . . .
H321 H 0.515343 0.460040 0.132938 0.107 Uiso 1 1 calc R U . . .
C322 C 0.4260(5) 0.4646(7) 0.1077(4) 0.063(3) Uani 1 1 d . . . . .
H322 H 0.422664 0.425236 0.084090 0.076 Uiso 1 1 calc R U . . .
Cl1D Cl 0.4914(2) 0.3849(3) 0.02055(17) 0.0825(13) Uani 0.7 1 d . . P . .
Cl2D Cl 0.5962(2) 0.3695(4) 0.0999(2) 0.1043(19) Uani 0.7 1 d . . P . .
C1D C 0.5625(5) 0.4290(13) 0.0477(4) 0.073(6) Uani 0.7 1 d . . P . .
H1D1 H 0.558530 0.486481 0.055782 0.088 Uiso 0.7 1 calc R U P . .
H1D2 H 0.586652 0.426449 0.026767 0.088 Uiso 0.7 1 calc R U P . .
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'
O O 0.0106 0.0060 '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
C119 Ir1 C219 89.8(4) . . ?
C119 Ir1 N21 94.2(4) . . ?
C219 Ir1 N21 79.5(4) . . ?
C119 Ir1 N11 79.7(4) . . ?
C219 Ir1 N11 93.0(4) . . ?
N21 Ir1 N11 170.5(3) . . ?
C119 Ir1 N31 98.9(4) . . ?
C219 Ir1 N31 171.3(4) . . ?
N21 Ir1 N31 99.7(3) . . ?
N11 Ir1 N31 88.6(3) . . ?
C119 Ir1 N33 173.8(4) . . ?
C219 Ir1 N33 95.1(3) . . ?
N21 Ir1 N33 90.3(3) . . ?
N11 Ir1 N33 96.4(4) . . ?
N31 Ir1 N33 76.2(3) . . ?
C121 O11 C141 117.0(14) . . ?
C142 O12 C129 118(2) . . ?
C111 N11 C113 107.1(10) . . ?
C111 N11 Ir1 114.4(8) . . ?
C113 N11 Ir1 137.7(10) . . ?
C111 N12 C112 106.3(12) . . ?
C111 N12 C125 130.4(15) . . ?
C112 N12 C125 123.1(12) . . ?
N11 C111 N12 110.8(12) . . ?
N11 C111 C118 118.4(10) . . ?
N12 C111 C118 130.8(13) . . ?
N12 C112 C113 107.2(11) . . ?
N12 C112 C117 131.0(16) . . ?
C113 C112 C117 121.8(18) . . ?
N11 C113 C112 108.6(13) . . ?
N11 C113 C114 131.7(13) . . ?
C112 C113 C114 119.7(12) . . ?
C115 C114 C113 118.0(16) . . ?
C116 C115 C114 122.2(19) . . ?
C115 C116 C117 121.0(16) . . ?
C116 C117 C112 117.2(18) . . ?
C123 C118 C119 122.7(12) . . ?
C123 C118 C111 127.9(13) . . ?
C119 C118 C111 109.4(11) . . ?
C120 C119 C118 114.1(10) . . ?
C120 C119 Ir1 128.1(8) . . ?
C118 C119 Ir1 117.6(8) . . ?
C121 C120 C119 122.4(11) . . ?
O11 C121 C120 115.0(13) . . ?
O11 C121 C122 123.6(13) . . ?
C120 C121 C122 121.4(13) . . ?
C121 C122 C123 118.5(14) . . ?
C118 C123 C122 120.7(14) . . ?
N12 C125 C126 114.0(12) . . ?
C131 C126 C127 119.6(12) . . ?
C131 C126 C125 120.0(15) . . ?
C127 C126 C125 120.3(13) . . ?
C126 C127 C128 120.0 . . ?
C129 C128 C127 121.3(14) . . ?
C128 C129 O12 125(3) . . ?
C128 C129 C130 117.8(15) . . ?
O12 C129 C130 117(2) . . ?
C131 C130 C129 122(2) . . ?
C126 C131 C130 119(2) . . ?
C221 O21 C241 116.7(10) . . ?
C211 N21 C213 106.9(8) . . ?
C211 N21 Ir1 116.3(6) . . ?
C213 N21 Ir1 136.9(7) . . ?
C211 N22 C212 107.0(8) . . ?
C211 N22 C25 131.2(9) . . ?
C212 N22 C25 121.2(9) . . ?
N21 C211 N22 112.3(8) . . ?
N21 C211 C218 116.0(9) . . ?
N22 C211 C218 131.7(10) . . ?
N22 C212 C217 132.0(10) . . ?
N22 C212 C213 106.5(8) . . ?
C217 C212 C213 121.5(9) . . ?
C214 C213 N21 132.5(10) . . ?
C214 C213 C212 120.2(9) . . ?
N21 C213 C212 107.3(9) . . ?
C213 C214 C215 118.0(10) . . ?
C214 C215 C216 121.4(10) . . ?
C217 C216 C215 121.8(10) . . ?
C216 C217 C212 117.1(10) . . ?
C223 C218 C219 121.2(9) . . ?
C223 C218 C211 126.9(10) . . ?
C219 C218 C211 111.9(9) . . ?
C218 C219 C220 117.2(9) . . ?
C218 C219 Ir1 115.8(7) . . ?
C220 C219 Ir1 126.6(8) . . ?
C221 C220 C219 120.8(10) . . ?
C222 C221 O21 124.2(10) . . ?
C222 C221 C220 121.3(9) . . ?
O21 C221 C220 114.5(10) . . ?
C221 C222 C223 119.3(11) . . ?
C218 C223 C222 120.1(11) . . ?
C26Y C25 N22 119.6(12) . . ?
N22 C25 C26X 102.8(11) . . ?
C31X C26X C27X 120.0 . . ?
C31X C26X C25 115.6(11) . . ?
C27X C26X C25 124.4(11) . . ?
C26X C27X C28X 120.0 . . ?
C27X C28X C29X 120.0 . . ?
O22X C29X C30X 126.1(16) . . ?
O22X C29X C28X 113.9(16) . . ?
C30X C29X C28X 120.0 . . ?
C29X C30X C31X 120.0 . . ?
C26X C31X C30X 120.0 . . ?
C240 O22X C29X 118(3) . . ?
C31Y C26Y C27Y 120.0 . . ?
C31Y C26Y C25 120.5(12) . . ?
C27Y C26Y C25 119.5(12) . . ?
C26Y C27Y C28Y 120.0 . . ?
C29Y C28Y C27Y 120.0 . . ?
C30Y C29Y C28Y 120.0 . . ?
C30Y C29Y O22Y 115.5(15) . . ?
C28Y C29Y O22Y 124.3(15) . . ?
C29Y C30Y C31Y 120.0 . . ?
C26Y C31Y C30Y 120.0 . . ?
C240 O22Y C29Y 116(2) . . ?
C311 N31 C313 106.3(9) . . ?
C311 N31 Ir1 113.1(7) . . ?
C313 N31 Ir1 139.6(8) . . ?
C312 N32 C311 109.5(8) . . ?
C322 N33 C318 117.8(9) . . ?
C322 N33 Ir1 126.9(7) . . ?
C318 N33 Ir1 115.0(7) . . ?
N31 C311 N32 110.4(9) . . ?
N31 C311 C318 121.4(9) . . ?
N32 C311 C318 128.1(9) . . ?
N32 C312 C317 134.7(11) . . ?
N32 C312 C313 104.9(9) . . ?
C317 C312 C313 120.3(12) . . ?
N31 C313 C314 129.7(11) . . ?
N31 C313 C312 108.7(10) . . ?
C314 C313 C312 121.6(11) . . ?
C315 C314 C313 113.2(12) . . ?
C314 C315 C316 125.4(13) . . ?
C317 C316 C315 119.7(13) . . ?
C316 C317 C312 119.7(13) . . ?
C319 C318 N33 121.8(11) . . ?
C319 C318 C311 125.1(10) . . ?
N33 C318 C311 113.2(9) . . ?
C318 C319 C320 121.3(11) . . ?
C319 C320 C321 117.3(12) . . ?
C322 C321 C320 119.0(13) . . ?
N33 C322 C321 122.9(11) . . ?
Cl1D C1D Cl2D 105.8(9) . . ?
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 C119 1.994(10) . ?
Ir1 C219 2.009(9) . ?
Ir1 N21 2.037(8) . ?
Ir1 N11 2.061(8) . ?
Ir1 N31 2.142(8) . ?
Ir1 N33 2.192(9) . ?
O11 C121 1.373(16) . ?
O11 C141 1.386(17) . ?
O12 C142 1.35(4) . ?
O12 C129 1.359(19) . ?
N11 C111 1.337(16) . ?
N11 C113 1.358(14) . ?
N12 C111 1.362(15) . ?
N12 C112 1.378(19) . ?
N12 C125 1.47(2) . ?
C111 C118 1.472(18) . ?
C112 C113 1.381(19) . ?
C112 C117 1.41(2) . ?
C113 C114 1.40(2) . ?
C114 C115 1.375(18) . ?
C115 C116 1.37(3) . ?
C116 C117 1.38(3) . ?
C118 C123 1.354(19) . ?
C118 C119 1.446(15) . ?
C119 C120 1.392(15) . ?
C120 C121 1.375(17) . ?
C121 C122 1.38(2) . ?
C122 C123 1.38(2) . ?
C125 C126 1.515(18) . ?
C126 C131 1.36(2) . ?
C126 C127 1.389(10) . ?
C127 C128 1.390(10) . ?
C128 C129 1.34(3) . ?
C129 C130 1.40(3) . ?
C130 C131 1.37(3) . ?
O21 C221 1.381(11) . ?
O21 C241 1.414(14) . ?
N21 C211 1.315(13) . ?
N21 C213 1.395(11) . ?
N22 C211 1.345(13) . ?
N22 C212 1.385(12) . ?
N22 C25 1.492(15) . ?
C211 C218 1.483(13) . ?
C212 C217 1.391(13) . ?
C212 C213 1.402(14) . ?
C213 C214 1.378(14) . ?
C214 C215 1.378(14) . ?
C215 C216 1.386(16) . ?
C216 C217 1.364(15) . ?
C218 C223 1.392(15) . ?
C218 C219 1.405(15) . ?
C219 C220 1.407(13) . ?
C220 C221 1.399(15) . ?
C221 C222 1.358(16) . ?
C222 C223 1.402(15) . ?
C240 O22X 1.30(3) . ?
C240 O22Y 1.36(4) . ?
C25 C26Y 1.481(19) . ?
C25 C26X 1.57(2) . ?
C26X C31X 1.387(10) . ?
C26X C27X 1.387(10) . ?
C27X C28X 1.387(10) . ?
C28X C29X 1.388(10) . ?
C29X O22X 1.33(2) . ?
C29X C30X 1.388(10) . ?
C30X C31X 1.388(10) . ?
C26Y C31Y 1.375(10) . ?
C26Y C27Y 1.376(10) . ?
C27Y C28Y 1.376(10) . ?
C28Y C29Y 1.375(10) . ?
C29Y C30Y 1.375(10) . ?
C29Y O22Y 1.46(3) . ?
C30Y C31Y 1.375(10) . ?
N31 C311 1.334(13) . ?
N31 C313 1.367(14) . ?
N32 C312 1.336(14) . ?
N32 C311 1.361(12) . ?
N33 C322 1.332(14) . ?
N33 C318 1.358(14) . ?
C311 C318 1.442(16) . ?
C312 C317 1.376(16) . ?
C312 C313 1.429(16) . ?
C313 C314 1.392(16) . ?
C314 C315 1.389(17) . ?
C315 C316 1.398(19) . ?
C316 C317 1.313(19) . ?
C318 C319 1.343(15) . ?
C319 C320 1.373(17) . ?
C320 C321 1.392(19) . ?
C321 C322 1.370(17) . ?
Cl1D C1D 1.786(13) . ?
Cl2D C1D 1.816(15) . ?
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
C114 H114 N33 0.95 2.57 3.316(17) 135.3 . yes
C120 H120 N21 0.95 2.69 3.175(15) 112.4 . yes
C220 H220 N11 0.95 2.58 3.105(14) 114.9 . yes
C240 H24D^b O12 0.98 2.57 3.38(3) 140.1 8_556 yes
N32 H3N Cl1 0.88 2.24 3.035(9) 150.0 . yes
C319 H319 Cl1 0.95 2.93 3.806(12) 153.7 . yes
C321 H321 Cl2D 0.95 2.87 3.792(16) 164.9 . yes
C322 H322 Cl1D 0.95 2.99 3.721(12) 135.2 . yes
C1D H1D1 O21 0.99 2.45 3.14(2) 126.4 5_665 yes
