# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_03661_amarillo
_database_code_depnum_ccdc_archive 'CCDC 2423907'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles Hernaez '
;Laboratorio DRX Monocristal, SIdI, Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2025-02-14 deposited with the CCDC.	2026-05-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            AU-120_am_250K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 Cl Ir N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         571.06

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2615(3)
_cell_length_b                   8.3062(2)
_cell_length_c                   15.5606(5)
_cell_angle_alpha                92.2200(10)
_cell_angle_beta                 97.4400(10)
_cell_angle_gamma                110.3440(10)
_cell_volume                     988.72(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    177
_cell_measurement_theta_min      2.7439
_cell_measurement_theta_max      26.3228
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.028
_exptl_crystal_density_diffrn    1.918
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556

_exptl_absorpt_coefficient_mu    6.913
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.83

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            42159
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_full        25.41
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             3626
_reflns_number_gt                3276
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.1028
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         3626
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+7.7485P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.007
_refine_diff_density_min         -1.358
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1295(11) 0.6706(12) 0.1895(6) 0.040(2) Uani d . . . 1 . .
C C2 0.1399(10) 0.5028(11) 0.1684(6) 0.0363(19) Uani d . . . 1 . .
C C3 0.2052(11) 0.5075(11) 0.0858(5) 0.0348(18) Uani d . . . 1 . .
C C4 0.2374(11) 0.6763(11) 0.0578(6) 0.038(2) Uani d . . . 1 . .
C C5 0.1943(11) 0.7776(11) 0.1220(6) 0.041(2) Uani d . . . 1 . .
C C6 0.0681(15) 0.7243(17) 0.2686(8) 0.071(4) Uani d . . . 1 . .
H H6A -0.047875 0.728120 0.252447 0.106000 Uiso calc U . R 1 . .
H H6B 0.147891 0.837605 0.292962 0.106000 Uiso calc U . R 1 . .
H H6C 0.064441 0.641881 0.311431 0.106000 Uiso calc U . R 1 . .
C C7 0.0832(14) 0.3465(14) 0.2192(8) 0.060(3) Uani d . . . 1 . .
H H7A -0.034959 0.272847 0.194931 0.090000 Uiso calc U . R 1 . .
H H7B 0.086631 0.383210 0.279613 0.090000 Uiso calc U . R 1 . .
H H7C 0.161365 0.283085 0.215849 0.090000 Uiso calc U . R 1 . .
C C8 0.2213(15) 0.3599(13) 0.0337(7) 0.056(3) Uani d . . . 1 . .
H H8A 0.118373 0.309553 -0.010000 0.085000 Uiso calc U . R 1 . .
H H8B 0.231699 0.273377 0.071950 0.085000 Uiso calc U . R 1 . .
H H8C 0.324233 0.401047 0.005365 0.085000 Uiso calc U . R 1 . .
C C9 0.3041(15) 0.7359(16) -0.0248(6) 0.063(3) Uani d . . . 1 . .
H H9A 0.215733 0.676456 -0.074131 0.095000 Uiso calc U . R 1 . .
H H9B 0.409138 0.710649 -0.028749 0.095000 Uiso calc U . R 1 . .
H H9C 0.330475 0.859154 -0.024950 0.095000 Uiso calc U . R 1 . .
C C10 0.2000(16) 0.9596(13) 0.1165(10) 0.077(4) Uani d . . . 1 . .
H H10A 0.085449 0.958428 0.092002 0.116000 Uiso calc U . R 1 . .
H H10B 0.284476 1.017908 0.079645 0.116000 Uiso calc U . R 1 . .
H H10C 0.233684 1.019883 0.174307 0.116000 Uiso calc U . R 1 . .
C C11 0.5424(11) 0.4128(11) 0.2345(6) 0.0351(18) Uani d . . . 1 . .
H H11 0.488270 0.358530 0.178816 0.042000 Uiso calc U . R 1 . .
C C12 0.6202(12) 0.3297(11) 0.2911(6) 0.040(2) Uani d . . . 1 . .
H H12 0.619119 0.219192 0.274549 0.048000 Uiso calc U . R 1 . .
C C13 0.7008(11) 0.4106(11) 0.3730(6) 0.0380(19) Uani d . . . 1 . .
H H13 0.752973 0.354063 0.412761 0.046000 Uiso calc U . R 1 . .
C C14 0.7044(10) 0.5743(10) 0.3963(5) 0.0319(17) Uani d . . . 1 . .
C C15 0.7910(12) 0.6698(11) 0.4844(6) 0.040(2) Uani d . . . 1 . .
C C16 0.7100(12) 0.7964(12) 0.5091(5) 0.042(2) Uani d . . . 1 . .
H H16 0.763436 0.866022 0.565460 0.050000 Uiso calc U . R 1 . .
C C17 0.6317(11) 0.8790(10) 0.4447(5) 0.0355(19) Uani d . . . 1 . .
H H17 0.639787 0.997991 0.461692 0.043000 Uiso calc U . R 1 . .
C C18 0.6260(10) 0.8342(10) 0.3498(5) 0.0298(17) Uani d . . . 1 . .
C C19 0.6251(10) 0.6522(10) 0.3348(5) 0.0274(16) Uani d . . . 1 . .
C C23 0.9824(12) 0.7646(13) 0.4863(6) 0.047(2) Uani d . . . 1 . .
H H23A 0.999271 0.848068 0.443262 0.070000 Uiso calc U . R 1 . .
H H23B 1.038272 0.683381 0.473203 0.070000 Uiso calc U . R 1 . .
H H23C 1.033534 0.823917 0.543635 0.070000 Uiso calc U . R 1 . .
Cl Cl1 0.6670(3) 0.8605(3) 0.13358(14) 0.0430(5) Uani d . . . 1 . .
Ir Ir1 0.39576(4) 0.69699(3) 0.18351(2) 0.02548(12) Uani d . . . 1 . .
N N1 0.5415(8) 0.5700(8) 0.2568(4) 0.0262(13) Uani d . . . 1 . .
O O1 0.4876(7) 0.8530(7) 0.2997(4) 0.0334(12) Uani d . . . 1 . .
O O2 0.7908(7) 0.9536(7) 0.3326(4) 0.0369(13) Uani d . . . 1 . .
H H2O 0.800914 0.936542 0.281033 0.044000 Uiso calc U . R 1 . .
O O3 0.5206(9) 0.7433(9) 0.4892(4) 0.0467(16) Uani d . . . 1 . .
O O4 0.7808(10) 0.5501(9) 0.5492(4) 0.0547(18) Uani d . . . 1 . .
H H4O 0.684046 0.471138 0.539593 0.066000 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C5 . 1.438(14) ?
C1 C2 . 1.454(13) ?
C1 C6 . 1.499(14) ?
C1 Ir1 . 2.149(8) ?
C2 C3 . 1.454(13) ?
C2 C7 . 1.512(13) ?
C2 Ir1 . 2.144(8) ?
C3 C4 . 1.430(12) ?
C3 C8 . 1.497(12) ?
C3 Ir1 . 2.177(8) ?
C4 C5 . 1.437(13) ?
C4 C9 . 1.498(13) ?
C4 Ir1 . 2.173(8) ?
C5 C10 . 1.502(13) ?
C5 Ir1 . 2.132(8) ?
C11 N1 . 1.340(10) ?
C11 C12 . 1.369(12) ?
C12 C13 . 1.387(13) ?
C13 C14 . 1.383(12) ?
C14 C19 . 1.395(11) ?
C14 C15 . 1.512(12) ?
C15 O4 . 1.433(10) ?
C15 C16 . 1.492(13) ?
C15 C23 . 1.497(13) ?
C16 C17 . 1.445(13) ?
C16 O3 . 1.457(11) ?
C17 O3 . 1.449(10) ?
C17 C18 . 1.500(11) ?
C18 O1 . 1.357(10) ?
C18 O2 . 1.444(9) ?
C18 C19 . 1.517(11) ?
C19 N1 . 1.344(10) ?
Cl1 Ir1 . 2.426(2) ?
Ir1 O1 . 2.074(5) ?
Ir1 N1 . 2.118(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 C1 C2 . . 107.4(8) ?
C5 C1 C6 . . 126.2(9) ?
C2 C1 C6 . . 126.4(10) ?
C5 C1 Ir1 . . 69.8(5) ?
C2 C1 Ir1 . . 70.0(5) ?
C6 C1 Ir1 . . 124.0(7) ?
C3 C2 C1 . . 107.7(7) ?
C3 C2 C7 . . 125.3(9) ?
C1 C2 C7 . . 126.9(9) ?
C3 C2 Ir1 . . 71.6(5) ?
C1 C2 Ir1 . . 70.4(5) ?
C7 C2 Ir1 . . 126.4(6) ?
C4 C3 C2 . . 107.8(8) ?
C4 C3 C8 . . 124.9(9) ?
C2 C3 C8 . . 127.1(8) ?
C4 C3 Ir1 . . 70.6(5) ?
C2 C3 Ir1 . . 69.1(4) ?
C8 C3 Ir1 . . 130.0(6) ?
C3 C4 C5 . . 108.5(8) ?
C3 C4 C9 . . 125.3(9) ?
C5 C4 C9 . . 126.2(9) ?
C3 C4 Ir1 . . 71.0(5) ?
C5 C4 Ir1 . . 69.0(5) ?
C9 C4 Ir1 . . 126.1(6) ?
C4 C5 C1 . . 108.5(7) ?
C4 C5 C10 . . 126.3(10) ?
C1 C5 C10 . . 125.0(10) ?
C4 C5 Ir1 . . 72.0(5) ?
C1 C5 Ir1 . . 71.0(5) ?
C10 C5 Ir1 . . 127.0(7) ?
N1 C11 C12 . . 121.4(8) ?
C11 C12 C13 . . 119.1(8) ?
C14 C13 C12 . . 120.1(8) ?
C13 C14 C19 . . 117.5(7) ?
C13 C14 C15 . . 122.7(7) ?
C19 C14 C15 . . 119.8(7) ?
O4 C15 C16 . . 110.2(8) ?
O4 C15 C23 . . 104.9(7) ?
C16 C15 C23 . . 108.3(8) ?
O4 C15 C14 . . 110.1(7) ?
C16 C15 C14 . . 111.4(7) ?
C23 C15 C14 . . 111.7(8) ?
C17 C16 O3 . . 59.9(6) ?
C17 C16 C15 . . 121.9(7) ?
O3 C16 C15 . . 117.5(7) ?
C16 C17 O3 . . 60.5(6) ?
C16 C17 C18 . . 119.8(7) ?
O3 C17 C18 . . 115.1(6) ?
O1 C18 O2 . . 112.3(6) ?
O1 C18 C17 . . 112.4(7) ?
O2 C18 C17 . . 102.4(6) ?
O1 C18 C19 . . 110.6(6) ?
O2 C18 C19 . . 108.5(6) ?
C17 C18 C19 . . 110.3(7) ?
N1 C19 C14 . . 121.8(7) ?
N1 C19 C18 . . 114.8(7) ?
C14 C19 C18 . . 123.4(7) ?
O1 Ir1 N1 . . 77.3(2) ?
O1 Ir1 C5 . . 104.0(3) ?
N1 Ir1 C5 . . 165.3(3) ?
O1 Ir1 C2 . . 118.2(3) ?
N1 Ir1 C2 . . 100.2(3) ?
C5 Ir1 C2 . . 66.1(3) ?
O1 Ir1 C1 . . 92.8(3) ?
N1 Ir1 C1 . . 126.5(3) ?
C5 Ir1 C1 . . 39.2(4) ?
C2 Ir1 C1 . . 39.6(3) ?
O1 Ir1 C4 . . 141.1(3) ?
N1 Ir1 C4 . . 141.6(3) ?
C5 Ir1 C4 . . 39.0(4) ?
C2 Ir1 C4 . . 65.3(3) ?
C1 Ir1 C4 . . 65.4(3) ?
O1 Ir1 C3 . . 156.9(3) ?
N1 Ir1 C3 . . 107.8(3) ?
C5 Ir1 C3 . . 65.4(3) ?
C2 Ir1 C3 . . 39.3(3) ?
C1 Ir1 C3 . . 65.8(3) ?
C4 Ir1 C3 . . 38.4(3) ?
O1 Ir1 Cl1 . . 87.90(17) ?
N1 Ir1 Cl1 . . 86.31(18) ?
C5 Ir1 Cl1 . . 108.4(3) ?
C2 Ir1 Cl1 . . 153.9(3) ?
C1 Ir1 Cl1 . . 146.6(3) ?
C4 Ir1 Cl1 . . 93.9(2) ?
C3 Ir1 Cl1 . . 114.6(2) ?
C11 N1 C19 . . 119.8(7) ?
C11 N1 Ir1 . . 125.2(5) ?
C19 N1 Ir1 . . 114.7(5) ?
C18 O1 Ir1 . . 115.9(5) ?
C17 O3 C16 . . 59.6(6) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 C1 C2 C3 . . . . -2.2(9) ?
C6 C1 C2 C3 . . . . 179.7(8) ?
Ir1 C1 C2 C3 . . . . -62.2(5) ?
C5 C1 C2 C7 . . . . -178.7(8) ?
C6 C1 C2 C7 . . . . 3.2(14) ?
Ir1 C1 C2 C7 . . . . 121.3(9) ?
C5 C1 C2 Ir1 . . . . 60.0(6) ?
C6 C1 C2 Ir1 . . . . -118.1(9) ?
C1 C2 C3 C4 . . . . 1.1(9) ?
C7 C2 C3 C4 . . . . 177.7(8) ?
Ir1 C2 C3 C4 . . . . -60.3(6) ?
C1 C2 C3 C8 . . . . -173.6(8) ?
C7 C2 C3 C8 . . . . 3.0(14) ?
Ir1 C2 C3 C8 . . . . 125.0(9) ?
C1 C2 C3 Ir1 . . . . 61.5(5) ?
C7 C2 C3 Ir1 . . . . -122.0(8) ?
C2 C3 C4 C5 . . . . 0.4(9) ?
C8 C3 C4 C5 . . . . 175.2(8) ?
Ir1 C3 C4 C5 . . . . -58.9(6) ?
C2 C3 C4 C9 . . . . -179.4(8) ?
C8 C3 C4 C9 . . . . -4.5(14) ?
Ir1 C3 C4 C9 . . . . 121.3(9) ?
C2 C3 C4 Ir1 . . . . 59.3(5) ?
C8 C3 C4 Ir1 . . . . -125.8(9) ?
C3 C4 C5 C1 . . . . -1.8(9) ?
C9 C4 C5 C1 . . . . 178.0(8) ?
Ir1 C4 C5 C1 . . . . -62.0(6) ?
C3 C4 C5 C10 . . . . -176.7(9) ?
C9 C4 C5 C10 . . . . 3.1(14) ?
Ir1 C4 C5 C10 . . . . 123.1(9) ?
C3 C4 C5 Ir1 . . . . 60.2(6) ?
C9 C4 C5 Ir1 . . . . -120.0(9) ?
C2 C1 C5 C4 . . . . 2.5(9) ?
C6 C1 C5 C4 . . . . -179.4(9) ?
Ir1 C1 C5 C4 . . . . 62.7(6) ?
C2 C1 C5 C10 . . . . 177.5(8) ?
C6 C1 C5 C10 . . . . -4.4(14) ?
Ir1 C1 C5 C10 . . . . -122.4(9) ?
C2 C1 C5 Ir1 . . . . -60.2(5) ?
C6 C1 C5 Ir1 . . . . 117.9(9) ?
N1 C11 C12 C13 . . . . -0.4(14) ?
C11 C12 C13 C14 . . . . -1.1(13) ?
C12 C13 C14 C19 . . . . -0.1(12) ?
C12 C13 C14 C15 . . . . -179.6(8) ?
C13 C14 C15 O4 . . . . -30.7(12) ?
C19 C14 C15 O4 . . . . 149.7(8) ?
C13 C14 C15 C16 . . . . -153.2(8) ?
C19 C14 C15 C16 . . . . 27.2(11) ?
C13 C14 C15 C23 . . . . 85.5(10) ?
C19 C14 C15 C23 . . . . -94.1(10) ?
O4 C15 C16 C17 . . . . -152.0(8) ?
C23 C15 C16 C17 . . . . 93.8(10) ?
C14 C15 C16 C17 . . . . -29.5(11) ?
O4 C15 C16 O3 . . . . -82.0(9) ?
C23 C15 C16 O3 . . . . 163.7(7) ?
C14 C15 C16 O3 . . . . 40.5(10) ?
C15 C16 C17 O3 . . . . 105.5(9) ?
O3 C16 C17 C18 . . . . -103.7(8) ?
C15 C16 C17 C18 . . . . 1.7(12) ?
C16 C17 C18 O1 . . . . 151.1(7) ?
O3 C17 C18 O1 . . . . 82.1(9) ?
C16 C17 C18 O2 . . . . -88.2(8) ?
O3 C17 C18 O2 . . . . -157.2(7) ?
C16 C17 C18 C19 . . . . 27.1(10) ?
O3 C17 C18 C19 . . . . -41.9(10) ?
C13 C14 C19 N1 . . . . 2.7(12) ?
C15 C14 C19 N1 . . . . -177.7(7) ?
C13 C14 C19 C18 . . . . -177.2(7) ?
C15 C14 C19 C18 . . . . 2.4(12) ?
O1 C18 C19 N1 . . . . 25.2(9) ?
O2 C18 C19 N1 . . . . -98.4(8) ?
C17 C18 C19 N1 . . . . 150.2(7) ?
O1 C18 C19 C14 . . . . -154.9(7) ?
O2 C18 C19 C14 . . . . 81.5(9) ?
C17 C18 C19 C14 . . . . -29.9(10) ?
C12 C11 N1 C19 . . . . 3.0(12) ?
C12 C11 N1 Ir1 . . . . -170.6(7) ?
C14 C19 N1 C11 . . . . -4.2(11) ?
C18 C19 N1 C11 . . . . 175.7(7) ?
C14 C19 N1 Ir1 . . . . 170.0(6) ?
C18 C19 N1 Ir1 . . . . -10.0(8) ?
O2 C18 O1 Ir1 . . . . 92.7(6) ?
C17 C18 O1 Ir1 . . . . -152.5(5) ?
C19 C18 O1 Ir1 . . . . -28.7(8) ?
C18 C17 O3 C16 . . . . 111.5(9) ?
C15 C16 O3 C17 . . . . -112.8(8) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C23 H23A O2 . 0.97 2.66 3.424(11) 135.5 ?
C23 H23C O2 2_776 0.97 2.52 3.464(11) 163.6 ?
O2 H2O Cl1 . 0.83 2.37 3.112(6) 148.6 ?
O4 H4O O3 2_666 0.83 1.97 2.789(9) 169.2 ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_03791
_database_code_depnum_ccdc_archive 'CCDC 2466582'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles Hernaez'
;Laboratorio DRX Monocristal, SIdI, Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2026-05-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            AU-234
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 Cl Ir N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         555.02

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.8506(5)
_cell_length_b                   15.3649(7)
_cell_length_c                   17.0306(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3886.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4552
_cell_measurement_theta_min      3.0470
_cell_measurement_theta_max      23.9522
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear intense red'
_exptl_crystal_size_max          0.105
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.053
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2144

_exptl_absorpt_coefficient_mu    7.032
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.71

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'sealed x-ray tube'
_diffrn_source_type              ?
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18206
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             3547
_reflns_number_gt                2572
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0629
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_number_reflns         3547
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+2.1484P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.432
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4346(4) 0.5758(4) 0.3317(3) 0.0501(15) Uani d . . . 1 . .
C C2 0.5185(3) 0.6187(4) 0.3418(3) 0.0407(13) Uani d . . . 1 . .
C C3 0.5096(4) 0.7059(4) 0.3117(3) 0.0440(14) Uani d . . . 1 . .
C C4 0.4218(4) 0.7171(4) 0.2832(3) 0.0514(15) Uani d . . . 1 . .
C C5 0.3731(4) 0.6380(5) 0.2961(3) 0.0573(17) Uani d . . . 1 . .
C C6 0.4163(4) 0.4826(4) 0.3546(4) 0.077(2) Uani d . . . 1 . .
H H6A 0.433579 0.444776 0.312347 0.116000 Uiso calc U . R 1 . .
H H6B 0.353257 0.475486 0.365262 0.116000 Uiso calc U . R 1 . .
H H6C 0.450406 0.468353 0.400697 0.116000 Uiso calc U . R 1 . .
C C7 0.6032(3) 0.5747(4) 0.3712(4) 0.0598(17) Uani d . . . 1 . .
H H7A 0.625460 0.535749 0.331607 0.090000 Uiso calc U . R 1 . .
H H7B 0.589858 0.542531 0.418048 0.090000 Uiso calc U . R 1 . .
H H7C 0.647985 0.617992 0.382420 0.090000 Uiso calc U . R 1 . .
C C8 0.5830(4) 0.7723(4) 0.3096(4) 0.0654(18) Uani d . . . 1 . .
H H8A 0.616557 0.766291 0.261758 0.098000 Uiso calc U . R 1 . .
H H8B 0.622368 0.763940 0.353645 0.098000 Uiso calc U . R 1 . .
H H8C 0.557094 0.829541 0.312043 0.098000 Uiso calc U . R 1 . .
C C9 0.3827(6) 0.7968(5) 0.2464(4) 0.093(3) Uani d . . . 1 . .
H H9A 0.384132 0.790986 0.190251 0.140000 Uiso calc U . R 1 . .
H H9B 0.417317 0.846782 0.261678 0.140000 Uiso calc U . R 1 . .
H H9C 0.321540 0.803926 0.263449 0.140000 Uiso calc U . R 1 . .
C C10 0.2793(4) 0.6181(6) 0.2701(4) 0.106(3) Uani d . . . 1 . .
H H10A 0.280378 0.596004 0.217437 0.159000 Uiso calc U . R 1 . .
H H10B 0.243714 0.670298 0.271829 0.159000 Uiso calc U . R 1 . .
H H10C 0.253377 0.575350 0.304453 0.159000 Uiso calc U . R 1 . .
C C11 0.3434(3) 0.8308(3) 0.5014(3) 0.0368(12) Uani d . . . 1 . .
C C12 0.3179(3) 0.9255(3) 0.5003(3) 0.0424(13) Uani d . . . 1 . .
H H12 0.255436 0.938688 0.485973 0.051000 Uiso calc U . R 1 . .
C C13 0.3615(4) 0.9869(4) 0.5528(3) 0.0519(15) Uani d . . . 1 . .
H H13 0.326330 1.037257 0.570383 0.062000 Uiso calc U . R 1 . .
C C14 0.4338(4) 0.9554(4) 0.6048(3) 0.0484(15) Uani d . . . 1 . .
C C15 0.4809(3) 0.8748(3) 0.5823(3) 0.0364(12) Uani d . . . 1 . .
C C16 0.5666(3) 0.8559(4) 0.6090(3) 0.0439(14) Uani d . . . 1 . .
H H16 0.594412 0.891294 0.646041 0.053000 Uiso calc U . R 1 . .
C C17 0.6102(4) 0.7838(4) 0.5798(3) 0.0490(16) Uani d . . . 1 . .
H H17 0.667453 0.768954 0.597328 0.059000 Uiso calc U . R 1 . .
C C18 0.5673(3) 0.7342(4) 0.5242(3) 0.0448(14) Uani d . . . 1 . .
H H18 0.597489 0.686561 0.503149 0.054000 Uiso calc U . R 1 . .
C C19 0.4401(3) 0.8204(3) 0.5290(3) 0.0331(12) Uani d . . . 1 . .
Cl Cl1 0.33791(10) 0.60832(10) 0.50785(9) 0.0574(4) Uani d . . . 1 . .
Ir Ir1 0.41584(2) 0.68804(2) 0.40606(2) 0.03398(9) Uani d . . . 1 . .
N N1 0.4832(2) 0.7515(3) 0.4987(2) 0.0346(10) Uani d . . . 1 . .
O O1 0.3313(2) 0.7923(2) 0.43001(19) 0.0381(9) Uani d . . . 1 . .
O O2 0.2853(2) 0.7943(2) 0.5609(2) 0.0462(9) Uani d . . . 1 . .
H H2 0.294923 0.741934 0.564722 0.069000 Uiso calc U . R 1 . .
O O3 0.3840(3) 0.9816(2) 0.4695(2) 0.0562(11) Uani d . . . 1 . .
O O4 0.4540(3) 0.9954(3) 0.6642(2) 0.0681(12) Uani d . . . 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.420(7) ?
C1 C5 . 1.455(8) ?
C1 C6 . 1.508(8) ?
C1 Ir1 . 2.158(5) ?
C2 C3 . 1.440(7) ?
C2 C7 . 1.512(7) ?
C2 Ir1 . 2.158(5) ?
C3 C4 . 1.403(7) ?
C3 C8 . 1.494(7) ?
C3 Ir1 . 2.144(5) ?
C4 C5 . 1.431(9) ?
C4 C9 . 1.493(8) ?
C4 Ir1 . 2.141(5) ?
C5 C10 . 1.493(8) ?
C5 Ir1 . 2.121(5) ?
C11 O1 . 1.365(6) ?
C11 O2 . 1.444(6) ?
C11 C12 . 1.504(6) ?
C11 C19 . 1.518(7) ?
C12 O3 . 1.408(6) ?
C12 C13 . 1.452(7) ?
C13 O3 . 1.460(6) ?
C13 C14 . 1.474(8) ?
C14 O4 . 1.222(6) ?
C14 C15 . 1.473(8) ?
C15 C19 . 1.375(7) ?
C15 C16 . 1.383(7) ?
C16 C17 . 1.376(8) ?
C17 C18 . 1.372(7) ?
C18 N1 . 1.348(6) ?
C19 N1 . 1.341(6) ?
Cl1 Ir1 . 2.4175(14) ?
Ir1 O1 . 2.075(3) ?
Ir1 N1 . 2.108(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C5 . . 107.3(5) ?
C2 C1 C6 . . 124.5(6) ?
C5 C1 C6 . . 128.2(5) ?
C2 C1 Ir1 . . 70.8(3) ?
C5 C1 Ir1 . . 68.8(3) ?
C6 C1 Ir1 . . 125.7(4) ?
C1 C2 C3 . . 107.9(5) ?
C1 C2 C7 . . 124.3(5) ?
C3 C2 C7 . . 127.5(5) ?
C1 C2 Ir1 . . 70.8(3) ?
C3 C2 Ir1 . . 69.9(3) ?
C7 C2 Ir1 . . 129.8(4) ?
C4 C3 C2 . . 108.8(5) ?
C4 C3 C8 . . 125.8(6) ?
C2 C3 C8 . . 125.3(5) ?
C4 C3 Ir1 . . 70.8(3) ?
C2 C3 Ir1 . . 71.0(3) ?
C8 C3 Ir1 . . 125.4(4) ?
C3 C4 C5 . . 108.2(5) ?
C3 C4 C9 . . 127.5(6) ?
C5 C4 C9 . . 124.4(6) ?
C3 C4 Ir1 . . 71.0(3) ?
C5 C4 Ir1 . . 69.6(3) ?
C9 C4 Ir1 . . 124.5(4) ?
C4 C5 C1 . . 107.8(5) ?
C4 C5 C10 . . 126.8(7) ?
C1 C5 C10 . . 125.1(7) ?
C4 C5 Ir1 . . 71.1(3) ?
C1 C5 Ir1 . . 71.5(3) ?
C10 C5 Ir1 . . 127.9(4) ?
O1 C11 O2 . . 112.2(4) ?
O1 C11 C12 . . 112.1(4) ?
O2 C11 C12 . . 103.5(4) ?
O1 C11 C19 . . 110.7(4) ?
O2 C11 C19 . . 107.9(4) ?
C12 C11 C19 . . 110.1(4) ?
O3 C12 C13 . . 61.4(3) ?
O3 C12 C11 . . 114.9(4) ?
C13 C12 C11 . . 120.5(5) ?
C12 C13 O3 . . 57.8(3) ?
C12 C13 C14 . . 118.8(5) ?
O3 C13 C14 . . 113.5(5) ?
O4 C14 C15 . . 121.4(6) ?
O4 C14 C13 . . 120.8(6) ?
C15 C14 C13 . . 117.8(5) ?
C19 C15 C16 . . 119.7(5) ?
C19 C15 C14 . . 118.2(5) ?
C16 C15 C14 . . 122.0(5) ?
C17 C16 C15 . . 118.9(5) ?
C18 C17 C16 . . 118.6(5) ?
N1 C18 C17 . . 122.8(5) ?
N1 C19 C15 . . 121.5(4) ?
N1 C19 C11 . . 114.6(4) ?
C15 C19 C11 . . 123.9(4) ?
O1 Ir1 N1 . . 77.46(14) ?
O1 Ir1 C5 . . 105.79(19) ?
N1 Ir1 C5 . . 166.1(2) ?
O1 Ir1 C4 . . 93.19(18) ?
N1 Ir1 C4 . . 128.0(2) ?
C5 Ir1 C4 . . 39.2(2) ?
O1 Ir1 C3 . . 116.21(17) ?
N1 Ir1 C3 . . 101.15(18) ?
C5 Ir1 C3 . . 65.1(2) ?
C4 Ir1 C3 . . 38.24(19) ?
O1 Ir1 C1 . . 144.13(18) ?
N1 Ir1 C1 . . 138.41(19) ?
C5 Ir1 C1 . . 39.7(2) ?
C4 Ir1 C1 . . 65.7(2) ?
C3 Ir1 C1 . . 65.1(2) ?
O1 Ir1 C2 . . 155.24(17) ?
N1 Ir1 C2 . . 105.83(17) ?
C5 Ir1 C2 . . 65.5(2) ?
C4 Ir1 C2 . . 65.1(2) ?
C3 Ir1 C2 . . 39.13(19) ?
C1 Ir1 C2 . . 38.41(18) ?
O1 Ir1 Cl1 . . 87.74(10) ?
N1 Ir1 Cl1 . . 85.68(11) ?
C5 Ir1 Cl1 . . 107.83(19) ?
C4 Ir1 Cl1 . . 145.70(18) ?
C3 Ir1 Cl1 . . 155.93(15) ?
C1 Ir1 Cl1 . . 94.46(16) ?
C2 Ir1 Cl1 . . 116.83(15) ?
C19 N1 C18 . . 118.3(4) ?
C19 N1 Ir1 . . 115.2(3) ?
C18 N1 Ir1 . . 126.1(4) ?
C11 O1 Ir1 . . 115.5(3) ?
C12 O3 C13 . . 60.8(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 C1 C2 C3 . . . . -0.9(6) ?
C6 C1 C2 C3 . . . . 179.0(5) ?
Ir1 C1 C2 C3 . . . . -60.3(3) ?
C5 C1 C2 C7 . . . . -175.0(5) ?
C6 C1 C2 C7 . . . . 5.0(8) ?
Ir1 C1 C2 C7 . . . . 125.7(5) ?
C5 C1 C2 Ir1 . . . . 59.4(3) ?
C6 C1 C2 Ir1 . . . . -120.7(5) ?
C1 C2 C3 C4 . . . . -0.1(6) ?
C7 C2 C3 C4 . . . . 173.7(5) ?
Ir1 C2 C3 C4 . . . . -61.0(4) ?
C1 C2 C3 C8 . . . . -178.7(5) ?
C7 C2 C3 C8 . . . . -4.9(8) ?
Ir1 C2 C3 C8 . . . . 120.5(5) ?
C1 C2 C3 Ir1 . . . . 60.9(3) ?
C7 C2 C3 Ir1 . . . . -125.4(5) ?
C2 C3 C4 C5 . . . . 1.1(6) ?
C8 C3 C4 C5 . . . . 179.7(5) ?
Ir1 C3 C4 C5 . . . . -60.0(4) ?
C2 C3 C4 C9 . . . . -179.6(5) ?
C8 C3 C4 C9 . . . . -1.0(9) ?
Ir1 C3 C4 C9 . . . . 119.4(6) ?
C2 C3 C4 Ir1 . . . . 61.1(4) ?
C8 C3 C4 Ir1 . . . . -120.3(5) ?
C3 C4 C5 C1 . . . . -1.7(6) ?
C9 C4 C5 C1 . . . . 179.0(5) ?
Ir1 C4 C5 C1 . . . . -62.5(4) ?
C3 C4 C5 C10 . . . . -175.4(5) ?
C9 C4 C5 C10 . . . . 5.2(9) ?
Ir1 C4 C5 C10 . . . . 123.8(6) ?
C3 C4 C5 Ir1 . . . . 60.8(4) ?
C9 C4 C5 Ir1 . . . . -118.5(6) ?
C2 C1 C5 C4 . . . . 1.6(6) ?
C6 C1 C5 C4 . . . . -178.3(5) ?
Ir1 C1 C5 C4 . . . . 62.3(4) ?
C2 C1 C5 C10 . . . . 175.5(5) ?
C6 C1 C5 C10 . . . . -4.5(9) ?
Ir1 C1 C5 C10 . . . . -123.9(6) ?
C2 C1 C5 Ir1 . . . . -60.7(4) ?
C6 C1 C5 Ir1 . . . . 119.4(6) ?
O1 C11 C12 O3 . . . . -80.9(5) ?
O2 C11 C12 O3 . . . . 158.0(4) ?
C19 C11 C12 O3 . . . . 42.8(6) ?
O1 C11 C12 C13 . . . . -151.1(5) ?
O2 C11 C12 C13 . . . . 87.8(6) ?
C19 C11 C12 C13 . . . . -27.3(7) ?
C11 C12 C13 O3 . . . . 103.5(5) ?
O3 C12 C13 C14 . . . . -101.0(5) ?
C11 C12 C13 C14 . . . . 2.5(8) ?
C12 C13 C14 O4 . . . . -158.5(5) ?
O3 C13 C14 O4 . . . . 136.6(5) ?
C12 C13 C14 C15 . . . . 22.0(8) ?
O3 C13 C14 C15 . . . . -42.9(7) ?
O4 C14 C15 C19 . . . . 162.0(5) ?
C13 C14 C15 C19 . . . . -18.5(7) ?
O4 C14 C15 C16 . . . . -22.6(8) ?
C13 C14 C15 C16 . . . . 156.9(5) ?
C19 C15 C16 C17 . . . . 1.6(8) ?
C14 C15 C16 C17 . . . . -173.8(5) ?
C15 C16 C17 C18 . . . . 1.1(8) ?
C16 C17 C18 N1 . . . . -2.1(9) ?
C16 C15 C19 N1 . . . . -3.6(7) ?
C14 C15 C19 N1 . . . . 172.0(4) ?
C16 C15 C19 C11 . . . . 174.5(5) ?
C14 C15 C19 C11 . . . . -10.0(7) ?
O1 C11 C19 N1 . . . . -25.1(6) ?
O2 C11 C19 N1 . . . . 98.0(5) ?
C12 C11 C19 N1 . . . . -149.7(4) ?
O1 C11 C19 C15 . . . . 156.7(5) ?
O2 C11 C19 C15 . . . . -80.2(6) ?
C12 C11 C19 C15 . . . . 32.2(7) ?
C15 C19 N1 C18 . . . . 2.6(7) ?
C11 C19 N1 C18 . . . . -175.6(4) ?
C15 C19 N1 Ir1 . . . . -171.3(4) ?
C11 C19 N1 Ir1 . . . . 10.5(5) ?
C17 C18 N1 C19 . . . . 0.3(8) ?
C17 C18 N1 Ir1 . . . . 173.4(4) ?
O2 C11 O1 Ir1 . . . . -92.5(4) ?
C12 C11 O1 Ir1 . . . . 151.5(3) ?
C19 C11 O1 Ir1 . . . . 28.1(5) ?
C11 C12 O3 C13 . . . . -112.7(5) ?
C14 C13 O3 C12 . . . . 110.3(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 Cl1 . 0.82 2.36 3.097(4) 150.3 ?
C12 H12 Cl1 8_665 0.98 2.98 3.641(5) 126.2 ?
C13 H13 Cl1 8_665 0.98 2.88 3.582(6) 129.6 ?
C17 H17 O1 4_566 0.93 2.65 3.490(6) 150.5 ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_03916
_database_code_depnum_ccdc_archive 'CCDC 2466580'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles Hernaez'
;Laboratorio DRX Monocristal, SIdI, Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2026-05-15 downloaded from the CCDC.
;
_audit_creation_date             2023-10-09
_audit_creation_method           
;
Olex2 1.5-ac6-012
(compiled 2023.08.24 svn.re1ec1418 for Rigaku Oxford Diffraction, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H29 Cl Ir N O4, C H2 Cl2'
_chemical_formula_sum            'C23 H31 Cl3 Ir N O4'
_chemical_formula_weight         684.04
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H29ClIrNO4
_chemical_oxdiff_usercomment     'LB515 250K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.83030(10)
_cell_length_b                   11.61920(10)
_cell_length_c                   18.96850(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.8740(10)
_cell_angle_gamma                90
_cell_volume                     2597.96(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    37198
_cell_measurement_temperature    250.00(10)
_cell_measurement_theta_max      68.1630
_cell_measurement_theta_min      3.7250
_shelx_estimated_absorpt_T_max   0.688
_shelx_estimated_absorpt_T_min   0.183
_exptl_absorpt_coefficient_mu    13.025
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.91a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   intense
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ribbon
_exptl_crystal_F_000             1344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 0 0.0870
-1 -1 1 0.0837
-1 0 1 0.0903
-1 0 0 0.0965
0 0 -1 0.0138
0 0 1 0.0177
0 1 1 0.0649
0 1 0 0.0694
1 -1 0 0.0869
1 -1 1 0.0792
1 0 1 0.0528
1 1 1 0.0764
1 1 0 0.0908
1 0 0 0.0608

_exptl_crystal_recrystallization_method 'obtained from dichloromethane'
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.031
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9978 1.0007 -0.0021 0.0048 0.0199 -0.1850
-1.0010 -0.9984 0.9973 0.0828 0.1781 0.0290
-0.9997 0.0012 0.9965 0.0842 0.0957 -0.0748
-0.9992 0.0012 -0.0013 0.0034 0.1022 -0.0812
0.0005 -0.0000 -0.9978 -0.0808 0.0065 -0.0063
-0.0005 0.0000 0.9978 0.0808 -0.0065 0.0063
0.0008 0.9996 0.9969 0.0822 -0.0889 -0.0975
0.0013 0.9996 -0.0008 0.0014 -0.0824 -0.1038
0.9978 -1.0007 0.0021 -0.0048 -0.0199 0.1850
0.9973 -1.0007 0.9999 0.0760 -0.0264 0.1913
0.9987 -0.0011 0.9990 0.0774 -0.1088 0.0875
1.0000 0.9984 0.9982 0.0788 -0.1911 -0.0163
1.0005 0.9984 0.0004 -0.0020 -0.1846 -0.0226
0.9992 -0.0012 0.0013 -0.0034 -0.1022 0.0812

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47274
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.298
_diffrn_reflns_theta_min         4.248
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 174.00   0.25    0.05    --  105.24  77.00 120.00  376
  2  ω     97.00 165.00   0.25    0.05    --  105.24  61.00  90.00  272
  3  ω     79.00 163.00   0.25    0.05    --  105.24  77.00  60.00  336
  4  ω     85.00 177.00   0.25    0.05    --  105.24  61.00  30.00  368
  5  ω     30.00 125.00   0.25    0.05    --   48.41  51.00 -15.00  380
  6  ω     87.00 178.00   0.25    0.05    --  105.24  51.00 -15.00  364
  7  ω    123.00 171.00   0.25    0.05    --  105.24  15.00 -90.00  192
  8  ω     44.00  99.00   0.25    0.05    --  105.24  15.00 -90.00  220
  9  ω     27.00  52.00   0.25    0.05    --  105.24 -45.00  60.00  100
 10  ω     38.00  73.00   0.25    0.05    --  105.24 -61.00 120.00  140
 11  ω     31.00  56.00   0.25    0.05    --  105.24 -61.00  90.00  100
 12  ω     44.00  74.00   0.25    0.05    --  105.24 -61.00-120.00  120
 13  ω     39.00  72.00   0.25    0.05    --  105.24 -61.00-150.00  132
 14  ω     28.00  61.00   0.25    0.05    --  105.24 -51.00-161.00  132
 15  ω    -28.00  61.00   0.25    0.05    --   48.41 -51.00-161.00  356
 16  ω     87.00 175.00   0.25    0.05    --  105.24 125.00-180.00  352
 17  ω     27.00  53.00   0.25    0.05    --  105.24 -45.00 150.00  104
 18  ω     27.00  52.00   0.25    0.05    --  105.24 -45.00 120.00  100
 19  ω     27.00  52.00   0.25    0.05    --  105.24 -45.00 -30.00  100
 20  ω     58.00  84.00   0.25    0.05    --  105.24-125.00 -30.00  104
 21  ω     37.00 101.00   0.25    0.05    --  105.24 -95.00 -30.00  256
 22  ω    -75.00 -40.00   0.25    0.05    --  -87.75  77.00   0.00  140
 23  ω    -54.00 -11.00   0.25    0.05    --  -87.75  51.00 -15.00  172
 24  ω    -68.00 -13.00   0.25    0.05    --  -87.75  61.00 -60.00  220
 25  ω    -47.00 -10.00   0.25    0.05    --  -87.75  45.00-180.00  148
 26  ω    -68.00 -13.00   0.25    0.05    --  -87.75  61.00-120.00  220
 27  ω    -23.00  28.00   0.25    0.05    --  -50.29  19.00 -30.00  204
 28  ω    -54.00  27.00   0.25    0.05    --  -50.29  51.00 -15.00  324
 29  ω    -47.00 -21.00   0.25    0.05    --  -87.75  45.00  90.00  104
 30  ω    -47.00 -10.00   0.25    0.05    --  -87.75  45.00 150.00  148
 31  ω   -156.00 -84.00   0.25    0.05    --  -87.75 -95.00 -60.00  288
 32  ω   -122.00 -74.00   0.25    0.05    --  -50.29-125.00 -60.00  192
 33  ω   -156.00 -61.00   0.25    0.05    --  -87.75 -77.00  90.00  380
 34  ω   -124.00 -73.00   0.25    0.05    --  -87.75 -61.00  60.00  204
 35  ω   -113.00 -72.00   0.25    0.05    --  -87.75 -61.00  90.00  164
 36  ω   -124.00 -73.00   0.25    0.05    --  -87.75 -45.00 150.00  204
 37  ω   -126.00 -31.00   0.25    0.05    --  -50.29 -57.00  90.00  380
 38  ω   -126.00 -31.00   0.25    0.05    --  -50.29 -57.00  60.00  380
 39  ω   -166.00 -71.00   0.25    0.05    --  -87.75 -45.00 150.00  380
 40  ω   -166.00 -71.00   0.25    0.05    --  -87.75 -45.00  90.00  380
 41  ω   -167.00 -67.00   0.25    0.05    --  -87.75 -30.00  90.00  400
 42  ω   -167.00 -67.00   0.25    0.05    --  -87.75 -30.00  90.00  400
 43  ω   -165.00 -69.00   0.25    0.05    --  -87.75 -51.00-161.00  384
 44  ω   -127.00 -32.00   0.25    0.05    --  -50.29 -51.00-161.00  380
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0035174000
_diffrn_orient_matrix_UB_12      0.0015014000
_diffrn_orient_matrix_UB_13      0.0810011000
_diffrn_orient_matrix_UB_21      -0.1024181000
_diffrn_orient_matrix_UB_22      -0.0822905000
_diffrn_orient_matrix_UB_23      -0.0065803000
_diffrn_orient_matrix_UB_31      0.0811005000
_diffrn_orient_matrix_UB_32      -0.1039482000
_diffrn_orient_matrix_UB_33      0.0063801000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4696
_reflns_number_total             4745
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.91a 64-bit (release 29-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.91a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.073
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4745
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.103
_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)+(0.0234P)²+6.2746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0584
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.4900(3) 0.3953(3) 0.57922(19) 0.0378(8) Uani 1 1 d . . . . .
C2 C 0.5995(3) 0.3497(3) 0.5989(2) 0.0385(8) Uani 1 1 d . . . . .
C3 C 0.6621(3) 0.4331(3) 0.6440(2) 0.0407(8) Uani 1 1 d . . . . .
C4 C 0.5892(3) 0.5288(3) 0.6512(2) 0.0403(8) Uani 1 1 d . . . . .
C5 C 0.4814(3) 0.5056(3) 0.6133(2) 0.0372(8) Uani 1 1 d . . . . .
C6 C 0.3975(4) 0.3410(5) 0.5327(2) 0.0609(13) Uani 1 1 d . . . . .
H6A H 0.387183 0.382945 0.488380 0.091 Uiso 1 1 calc R U . . .
H6B H 0.327565 0.342941 0.555934 0.091 Uiso 1 1 calc R U . . .
H6C H 0.417314 0.261796 0.523377 0.091 Uiso 1 1 calc R U . . .
C7 C 0.6440(5) 0.2359(4) 0.5776(3) 0.0628(13) Uani 1 1 d . . . . .
H7A H 0.581121 0.183901 0.565732 0.094 Uiso 1 1 calc R U . . .
H7B H 0.692813 0.204020 0.616418 0.094 Uiso 1 1 calc R U . . .
H7C H 0.687087 0.245784 0.536703 0.094 Uiso 1 1 calc R U . . .
C8 C 0.7860(4) 0.4231(5) 0.6691(3) 0.0673(14) Uani 1 1 d . . . . .
H8A H 0.801058 0.346839 0.688536 0.101 Uiso 1 1 calc R U . . .
H8B H 0.805149 0.480380 0.705353 0.101 Uiso 1 1 calc R U . . .
H8C H 0.831554 0.435514 0.629623 0.101 Uiso 1 1 calc R U . . .
C9 C 0.6177(5) 0.6407(4) 0.6886(3) 0.0665(14) Uani 1 1 d . . . . .
H9A H 0.692091 0.634921 0.714156 0.100 Uiso 1 1 calc R U . . .
H9B H 0.561509 0.656835 0.721674 0.100 Uiso 1 1 calc R U . . .
H9C H 0.617904 0.702387 0.654188 0.100 Uiso 1 1 calc R U . . .
C10 C 0.3819(4) 0.5848(5) 0.6049(3) 0.0655(14) Uani 1 1 d . . . . .
H10A H 0.387575 0.632759 0.563461 0.098 Uiso 1 1 calc R U . . .
H10B H 0.380922 0.633072 0.646513 0.098 Uiso 1 1 calc R U . . .
H10C H 0.312585 0.539955 0.599113 0.098 Uiso 1 1 calc R U . . .
C11 C 0.5565(4) 0.4849(4) 0.8441(2) 0.0506(10) Uani 1 1 d . . . . .
C12 C 0.5167(5) 0.5472(4) 0.8989(2) 0.0624(13) Uani 1 1 d . . . . .
H12 H 0.568652 0.579616 0.933552 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4028(5) 0.5624(4) 0.9035(2) 0.0612(13) Uani 1 1 d . . . . .
H13 H 0.377353 0.611106 0.938404 0.073 Uiso 1 1 calc R U . . .
C14 C 0.3243(4) 0.5058(3) 0.8564(2) 0.0449(10) Uani 1 1 d . . . . .
C15 C 0.1975(4) 0.5141(3) 0.8610(2) 0.0501(11) Uani 1 1 d . . . . .
C16 C 0.1336(4) 0.4869(3) 0.7910(2) 0.0470(10) Uani 1 1 d . . . . .
H16 H 0.049881 0.488588 0.790832 0.056 Uiso 1 1 calc R U . . .
C17 C 0.1784(3) 0.4100(3) 0.7388(2) 0.0372(8) Uani 1 1 d . . . . .
C18 C 0.2949(3) 0.3586(3) 0.75804(19) 0.0327(7) Uani 1 1 d . . . . .
C19 C 0.3686(3) 0.4400(3) 0.80427(17) 0.0343(8) Uani 1 1 d . . . . .
C20 C 0.6806(4) 0.4646(5) 0.8385(3) 0.0686(14) Uani 1 1 d . . . . .
H20A H 0.711515 0.526850 0.812082 0.103 Uiso 1 1 calc R U . . .
H20B H 0.690943 0.392242 0.814361 0.103 Uiso 1 1 calc R U . . .
H20C H 0.719623 0.461416 0.885597 0.103 Uiso 1 1 calc R U . . .
C21 C 0.1026(3) 0.3435(4) 0.6862(3) 0.0565(12) Uani 1 1 d . . . . .
H21A H 0.093431 0.265808 0.703471 0.085 Uiso 1 1 calc R U . . .
H21B H 0.136248 0.340959 0.641348 0.085 Uiso 1 1 calc R U . . .
H21C H 0.029109 0.380824 0.679765 0.085 Uiso 1 1 calc R U . . .
C22 C 0.1601(5) 0.4326(4) 0.9177(3) 0.0729(17) Uani 1 1 d . . . . .
H22A H 0.188582 0.355895 0.909661 0.109 Uiso 1 1 calc R U . . .
H22B H 0.077918 0.430801 0.915578 0.109 Uiso 1 1 calc R U . . .
H22C H 0.190085 0.459479 0.964023 0.109 Uiso 1 1 calc R U . . .
Cl1 Cl 0.57541(8) 0.20104(8) 0.75031(5) 0.0455(2) Uani 1 1 d . . . . .
Ir1 Ir 0.51267(2) 0.37688(2) 0.69277(2) 0.02769(6) Uani 1 1 d . . . . .
N008 N 0.4806(3) 0.4374(3) 0.79438(16) 0.0374(7) Uani 1 1 d . . . . .
O1 O 0.34601(18) 0.3226(2) 0.70001(12) 0.0305(5) Uani 1 1 d . . . . .
O2 O 0.2736(3) 0.2630(2) 0.80379(15) 0.0486(7) Uani 1 1 d . . . . .
H2 H 0.298704 0.202949 0.787266 0.073 Uiso 1 1 calc R U . . .
O3 O 0.1789(2) 0.5338(2) 0.72812(14) 0.0430(6) Uani 1 1 d . . . . .
O4 O 0.1690(4) 0.6268(2) 0.88378(17) 0.0643(10) Uani 1 1 d . . . . .
H4 H 0.167330 0.671851 0.849750 0.096 Uiso 1 1 calc R U . . .
C23 C 0.4876(5) 0.1642(8) 0.9216(3) 0.096(2) Uani 1 1 d . . . . .
H23A H 0.467882 0.219759 0.883709 0.116 Uiso 1 1 calc R U . . .
H23B H 0.478334 0.086712 0.901560 0.116 Uiso 1 1 calc R U . . .
Cl2 Cl 0.62902(15) 0.1842(3) 0.95381(10) 0.1372(9) Uani 1 1 d . . . . .
Cl3 Cl 0.40020(19) 0.1806(4) 0.98481(13) 0.1721(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.421(6) . ?
C1 C5 1.443(5) . ?
C1 C6 1.487(6) . ?
C1 Ir1 2.159(4) . ?
C2 C3 1.453(6) . ?
C2 C7 1.492(6) . ?
C2 Ir1 2.153(4) . ?
C3 C4 1.420(5) . ?
C3 C8 1.507(5) . ?
C3 Ir1 2.165(4) . ?
C4 C5 1.434(5) . ?
C4 C9 1.506(6) . ?
C4 Ir1 2.163(4) . ?
C5 C10 1.491(5) . ?
C5 Ir1 2.134(3) . ?
C11 C12 1.381(7) . ?
C11 C20 1.499(7) . ?
C11 N008 1.362(5) . ?
C12 C13 1.369(8) . ?
C13 C14 1.397(7) . ?
C14 C15 1.513(6) . ?
C14 C19 1.388(5) . ?
C15 C16 1.504(7) . ?
C15 C22 1.527(6) . ?
C15 O4 1.428(4) . ?
C16 C17 1.467(5) . ?
C16 O3 1.455(4) . ?
C17 C18 1.518(5) . ?
C17 C21 1.497(6) . ?
C17 O3 1.453(4) . ?
C18 C19 1.515(5) . ?
C18 O1 1.366(4) . ?
C18 O2 1.445(4) . ?
C19 N008 1.354(5) . ?
Cl1 Ir1 2.4039(9) . ?
Ir1 N008 2.116(3) . ?
Ir1 O1 2.086(2) . ?
C23 Cl2 1.747(6) . ?
C23 Cl3 1.659(6) . ?

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 108.1(3) . . ?
C2 C1 C6 127.4(4) . . ?
C2 C1 Ir1 70.6(2) . . ?
C5 C1 C6 124.5(4) . . ?
C5 C1 Ir1 69.4(2) . . ?
C6 C1 Ir1 125.0(3) . . ?
C1 C2 C3 108.3(3) . . ?
C1 C2 C7 126.5(4) . . ?
C1 C2 Ir1 71.0(2) . . ?
C3 C2 C7 125.3(4) . . ?
C3 C2 Ir1 70.8(2) . . ?
C7 C2 Ir1 124.0(3) . . ?
C2 C3 C8 124.6(4) . . ?
C2 C3 Ir1 69.9(2) . . ?
C4 C3 C2 107.2(3) . . ?
C4 C3 C8 127.8(4) . . ?
C4 C3 Ir1 70.8(2) . . ?
C8 C3 Ir1 130.4(3) . . ?
C3 C4 C5 109.0(3) . . ?
C3 C4 C9 127.4(4) . . ?
C3 C4 Ir1 70.9(2) . . ?
C5 C4 C9 123.5(4) . . ?
C5 C4 Ir1 69.40(19) . . ?
C9 C4 Ir1 128.0(3) . . ?
C1 C5 C10 125.7(4) . . ?
C1 C5 Ir1 71.3(2) . . ?
C4 C5 C1 107.3(3) . . ?
C4 C5 C10 126.7(4) . . ?
C4 C5 Ir1 71.6(2) . . ?
C10 C5 Ir1 126.6(3) . . ?
C12 C11 C20 122.3(4) . . ?
N008 C11 C12 119.1(4) . . ?
N008 C11 C20 118.6(4) . . ?
C13 C12 C11 121.1(4) . . ?
C12 C13 C14 120.2(4) . . ?
C13 C14 C15 122.8(4) . . ?
C19 C14 C13 116.4(4) . . ?
C19 C14 C15 120.9(4) . . ?
C14 C15 C22 110.5(4) . . ?
C16 C15 C14 111.2(3) . . ?
C16 C15 C22 109.7(4) . . ?
O4 C15 C14 109.7(4) . . ?
O4 C15 C16 110.2(4) . . ?
O4 C15 C22 105.4(3) . . ?
C17 C16 C15 122.7(4) . . ?
O3 C16 C15 116.9(4) . . ?
O3 C16 C17 59.6(2) . . ?
C16 C17 C18 116.7(4) . . ?
C16 C17 C21 122.3(4) . . ?
C21 C17 C18 115.9(3) . . ?
O3 C17 C16 59.8(2) . . ?
O3 C17 C18 114.1(3) . . ?
O3 C17 C21 115.3(3) . . ?
C19 C18 C17 111.1(3) . . ?
O1 C18 C17 112.4(3) . . ?
O1 C18 C19 112.6(3) . . ?
O1 C18 O2 111.1(3) . . ?
O2 C18 C17 104.3(3) . . ?
O2 C18 C19 104.7(3) . . ?
C14 C19 C18 121.5(4) . . ?
N008 C19 C14 123.0(4) . . ?
N008 C19 C18 115.4(3) . . ?
C1 Ir1 C3 65.18(15) . . ?
C1 Ir1 C4 64.87(14) . . ?
C1 Ir1 Cl1 123.01(11) . . ?
C2 Ir1 C1 38.47(15) . . ?
C2 Ir1 C3 39.32(15) . . ?
C2 Ir1 C4 64.80(14) . . ?
C2 Ir1 Cl1 95.74(11) . . ?
C3 Ir1 Cl1 102.65(11) . . ?
C4 Ir1 C3 38.32(15) . . ?
C4 Ir1 Cl1 137.45(11) . . ?
C5 Ir1 C1 39.30(15) . . ?
C5 Ir1 C2 65.48(14) . . ?
C5 Ir1 C3 65.47(14) . . ?
C5 Ir1 C4 38.99(15) . . ?
C5 Ir1 Cl1 160.91(10) . . ?
N008 Ir1 C1 149.23(14) . . ?
N008 Ir1 C2 159.54(14) . . ?
N008 Ir1 C3 120.34(14) . . ?
N008 Ir1 C4 100.02(13) . . ?
N008 Ir1 C5 112.13(13) . . ?
N008 Ir1 Cl1 86.63(9) . . ?
O1 Ir1 C1 93.29(12) . . ?
O1 Ir1 C2 122.01(12) . . ?
O1 Ir1 C3 158.46(12) . . ?
O1 Ir1 C4 134.26(13) . . ?
O1 Ir1 C5 98.66(12) . . ?
O1 Ir1 Cl1 88.29(7) . . ?
O1 Ir1 N008 78.30(10) . . ?
C11 N008 Ir1 127.4(3) . . ?
C19 N008 C11 119.4(3) . . ?
C19 N008 Ir1 112.7(2) . . ?
C18 O1 Ir1 116.5(2) . . ?
C17 O3 C16 60.6(2) . . ?
Cl3 C23 Cl2 111.7(3) . . ?

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 0.99 2.95 3.548(4) 119.8 2_556 yes
C20 H20B Cl1 0.97 2.83 3.657(5) 143.9 . yes
C22 H22A O2 0.97 2.56 3.294(5) 132.6 . yes
O2 H2 O3 0.83 2.01 2.799(4) 159.0 2_546 yes
O4 H4 O1 0.83 1.99 2.772(4) 156.9 2_556 yes
C23 H23A Cl1 0.98 2.94 3.521(6) 119.4 . 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
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 C8 -172.7(4) . . . . ?
C1 C2 C3 Ir1 61.4(2) . . . . ?
C2 C1 C5 C4 2.7(4) . . . . ?
C2 C1 C5 C10 177.7(4) . . . . ?
C2 C1 C5 Ir1 -60.2(2) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C2 C3 C4 C9 -175.5(4) . . . . ?
C2 C3 C4 Ir1 60.7(3) . . . . ?
C3 C4 C5 C1 -2.7(4) . . . . ?
C3 C4 C5 C10 -177.6(4) . . . . ?
C3 C4 C5 Ir1 60.0(3) . . . . ?
C5 C1 C2 C3 -1.8(4) . . . . ?
C5 C1 C2 C7 178.2(4) . . . . ?
C5 C1 C2 Ir1 59.5(2) . . . . ?
C6 C1 C2 C3 179.0(4) . . . . ?
C6 C1 C2 C7 -1.0(6) . . . . ?
C6 C1 C2 Ir1 -119.7(4) . . . . ?
C6 C1 C5 C4 -178.0(3) . . . . ?
C6 C1 C5 C10 -3.1(6) . . . . ?
C6 C1 C5 Ir1 119.0(4) . . . . ?
C7 C2 C3 C4 -179.9(4) . . . . ?
C7 C2 C3 C8 7.4(6) . . . . ?
C7 C2 C3 Ir1 -118.6(4) . . . . ?
C8 C3 C4 C5 174.1(4) . . . . ?
C8 C3 C4 C9 -3.0(7) . . . . ?
C8 C3 C4 Ir1 -126.8(4) . . . . ?
C9 C4 C5 C1 174.5(4) . . . . ?
C9 C4 C5 C10 -0.3(6) . . . . ?
C9 C4 C5 Ir1 -122.7(4) . . . . ?
C11 C12 C13 C14 6.1(7) . . . . ?
C12 C11 N008 C19 -8.1(6) . . . . ?
C12 C11 N008 Ir1 162.7(3) . . . . ?
C12 C13 C14 C15 176.7(4) . . . . ?
C12 C13 C14 C19 -3.0(6) . . . . ?
C13 C14 C15 C16 157.5(4) . . . . ?
C13 C14 C15 C22 -80.4(5) . . . . ?
C13 C14 C15 O4 35.3(5) . . . . ?
C13 C14 C19 C18 169.4(3) . . . . ?
C13 C14 C19 N008 -5.9(5) . . . . ?
C14 C15 C16 C17 28.3(5) . . . . ?
C14 C15 C16 O3 -41.4(4) . . . . ?
C14 C19 N008 C11 11.6(5) . . . . ?
C14 C19 N008 Ir1 -160.5(3) . . . . ?
C15 C14 C19 C18 -10.3(5) . . . . ?
C15 C14 C19 N008 174.4(3) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C15 C16 C17 C21 153.2(4) . . . . ?
C15 C16 C17 O3 -104.3(4) . . . . ?
C15 C16 O3 C17 113.9(4) . . . . ?
C16 C17 C18 C19 -31.5(4) . . . . ?
C16 C17 C18 O1 -158.8(3) . . . . ?
C16 C17 C18 O2 80.7(4) . . . . ?
C17 C18 C19 C14 38.3(4) . . . . ?
C17 C18 C19 N008 -146.1(3) . . . . ?
C17 C18 O1 Ir1 130.6(3) . . . . ?
C18 C17 O3 C16 -108.0(4) . . . . ?
C18 C19 N008 C11 -163.9(3) . . . . ?
C18 C19 N008 Ir1 24.0(4) . . . . ?
C19 C14 C15 C16 -22.8(5) . . . . ?
C19 C14 C15 C22 99.3(4) . . . . ?
C19 C14 C15 O4 -145.0(3) . . . . ?
C19 C18 O1 Ir1 4.2(4) . . . . ?
C20 C11 C12 C13 -178.6(5) . . . . ?
C20 C11 N008 C19 170.1(4) . . . . ?
C20 C11 N008 Ir1 -19.1(6) . . . . ?
C21 C17 C18 C19 173.0(3) . . . . ?
C21 C17 C18 O1 45.7(4) . . . . ?
C21 C17 C18 O2 -74.8(4) . . . . ?
C21 C17 O3 C16 114.1(4) . . . . ?
C22 C15 C16 C17 -94.3(4) . . . . ?
C22 C15 C16 O3 -163.9(3) . . . . ?
Ir1 C1 C2 C3 -61.3(3) . . . . ?
Ir1 C1 C2 C7 118.7(4) . . . . ?
Ir1 C1 C5 C4 63.0(2) . . . . ?
Ir1 C1 C5 C10 -122.1(4) . . . . ?
Ir1 C2 C3 C4 -61.3(3) . . . . ?
Ir1 C2 C3 C8 125.9(4) . . . . ?
Ir1 C3 C4 C5 -59.1(3) . . . . ?
Ir1 C3 C4 C9 123.8(4) . . . . ?
Ir1 C4 C5 C1 -62.7(2) . . . . ?
Ir1 C4 C5 C10 122.4(4) . . . . ?
N008 C11 C12 C13 -0.5(7) . . . . ?
O1 C18 C19 C14 165.5(3) . . . . ?
O1 C18 C19 N008 -18.9(4) . . . . ?
O2 C18 C19 C14 -73.7(4) . . . . ?
O2 C18 C19 N008 101.9(3) . . . . ?
O2 C18 O1 Ir1 -112.9(3) . . . . ?
O3 C16 C17 C18 103.7(3) . . . . ?
O3 C16 C17 C21 -102.5(4) . . . . ?
O3 C17 C18 C19 35.4(4) . . . . ?
O3 C17 C18 O1 -91.9(4) . . . . ?
O3 C17 C18 O2 147.7(3) . . . . ?
O4 C15 C16 C17 150.1(4) . . . . ?
O4 C15 C16 O3 80.5(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'placed on a MiTeGen micromount'
_olex2_submission_original_sample_id LB515
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.082
_oxdiff_exptl_absorpt_empirical_full_min 0.701
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_03854
_database_code_depnum_ccdc_archive 'CCDC 2466583'
loop_
_audit_author_name
_audit_author_address
' Josefina Perles Hernaez'
;Laboratorio DRX Monocristal, SIdI, Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2026-05-15 downloaded from the CCDC.
;
_audit_creation_date             2023-07-03
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H27 Cl Ir N O'
_chemical_formula_sum            'C22 H27 Cl Ir N O'
_chemical_formula_weight         549.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H27ClIrNO
_chemical_oxdiff_usercomment     LB483
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4047(4)
_cell_length_b                   15.4037(8)
_cell_length_c                   16.1333(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.707(5)
_cell_angle_gamma                90
_cell_volume                     2064.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8612
_cell_measurement_temperature    296.30
_cell_measurement_theta_max      30.4150
_cell_measurement_theta_min      2.5810
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.637
_exptl_absorpt_coefficient_mu    6.607
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0331
1 -1 0 0.0328
0 1 0 0.0084
0 -1 0 0.0099
0 1 1 0.0121
0 -1 -1 0.0151
0 0 1 0.0088
0 0 -1 0.0118
0 1 -1 0.0069
-1 0 1 0.0346
-1 0 -1 0.0377
1 -1 -1 0.0365

_exptl_crystal_recrystallization_method 'obtained from dichloromethane'
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.018
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0017 -0.0187 -0.0197 -0.0325 0.0511 0.0602
0.9958 -1.0195 -0.0170 -0.0565 0.0156 0.0773
0.0059 1.0008 -0.0028 0.0240 0.0354 -0.0171
-0.0059 -1.0008 0.0028 -0.0240 -0.0354 0.0171
0.0110 1.0020 0.9977 -0.0122 0.0494 -0.0390
-0.0110 -1.0020 -0.9977 0.0122 -0.0494 0.0390
0.0051 0.0012 1.0005 -0.0363 0.0140 -0.0219
-0.0051 -0.0012 -1.0005 0.0363 -0.0140 0.0219
0.0008 0.9996 -1.0033 0.0603 0.0215 0.0048
-0.9966 0.0199 1.0202 -0.0038 -0.0371 -0.0821
-1.0069 0.0175 -0.9808 0.0688 -0.0650 -0.0383
0.9907 -1.0207 -1.0175 -0.0203 0.0017 0.0992

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23657
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.517
_diffrn_reflns_theta_min         2.554
_diffrn_ambient_temperature      296.30
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  34.00   0.50   60.02    --    4.42 -91.00  -0.00  150
  2  ω    -25.00  42.00   0.50   60.02    --    4.42  91.00 112.00  134
  3  ω    -23.00  28.00   0.50   60.02    --   -4.34 -99.00 120.00  102
  4  ω    -18.00  17.00   0.50   60.02    --   -4.34 -99.00-180.00   70
  5  ω    -22.00   5.00   0.50   60.02    --   -4.34 -99.00-120.00   54
  6  ω    -14.00  12.00   0.50   60.02    --   -4.34 -99.00 -90.00   52
  7  ω    -15.00  30.00   0.50   60.02    --    4.42 -99.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0327053000
_diffrn_orient_matrix_UB_12      0.0240835000
_diffrn_orient_matrix_UB_13      -0.0360946000
_diffrn_orient_matrix_UB_21      0.0518940000
_diffrn_orient_matrix_UB_22      0.0351271000
_diffrn_orient_matrix_UB_23      0.0136486000
_diffrn_orient_matrix_UB_31      0.0593189000
_diffrn_orient_matrix_UB_32      -0.0175083000
_diffrn_orient_matrix_UB_33      -0.0221609000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3907
_reflns_number_total             5213
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         5213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0182P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0520
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C16(H16)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.2720(4) 0.7748(3) 0.7756(3) 0.0478(10) Uani 1 1 d . . . . .
C2 C 0.1946(4) 0.6930(3) 0.7878(3) 0.0474(10) Uani 1 1 d . . . . .
C3 C 0.0872(4) 0.6749(2) 0.7119(3) 0.0421(9) Uani 1 1 d . . . . .
C4 C 0.0976(4) 0.7436(2) 0.6531(3) 0.0442(9) Uani 1 1 d . . . . .
C5 C 0.2110(5) 0.8054(2) 0.6936(3) 0.0501(11) Uani 1 1 d . . . . .
C6 C 0.3952(5) 0.8190(3) 0.8385(3) 0.0752(16) Uani 1 1 d . . . . .
H6A H 0.342081 0.857104 0.872667 0.113 Uiso 1 1 calc R U . . .
H6B H 0.466890 0.852027 0.809793 0.113 Uiso 1 1 calc R U . . .
H6C H 0.455363 0.776168 0.873389 0.113 Uiso 1 1 calc R U . . .
C7 C 0.2185(6) 0.6411(3) 0.8666(3) 0.0714(14) Uani 1 1 d . . . . .
H7A H 0.331589 0.633151 0.885138 0.107 Uiso 1 1 calc R U . . .
H7B H 0.167653 0.585530 0.856454 0.107 Uiso 1 1 calc R U . . .
H7C H 0.171687 0.671243 0.909122 0.107 Uiso 1 1 calc R U . . .
C8 C -0.0246(5) 0.5981(3) 0.6975(3) 0.0627(13) Uani 1 1 d . . . . .
H8A H 0.011610 0.553360 0.737311 0.094 Uiso 1 1 calc R U . . .
H8B H -0.025335 0.576405 0.641683 0.094 Uiso 1 1 calc R U . . .
H8C H -0.131450 0.615722 0.704356 0.094 Uiso 1 1 calc R U . . .
C9 C -0.0138(5) 0.7592(3) 0.5728(3) 0.0671(13) Uani 1 1 d . . . . .
H9A H -0.057220 0.704844 0.550793 0.101 Uiso 1 1 calc R U . . .
H9B H 0.044488 0.786179 0.532961 0.101 Uiso 1 1 calc R U . . .
H9C H -0.099989 0.796577 0.583279 0.101 Uiso 1 1 calc R U . . .
C10 C 0.2556(6) 0.8890(3) 0.6557(4) 0.0808(17) Uani 1 1 d . . . . .
H10A H 0.183507 0.934041 0.667783 0.121 Uiso 1 1 calc R U . . .
H10B H 0.248001 0.882284 0.596077 0.121 Uiso 1 1 calc R U . . .
H10C H 0.363912 0.904376 0.678936 0.121 Uiso 1 1 calc R U . . .
C11 C 0.2976(4) 0.5308(2) 0.5544(2) 0.0336(8) Uani 1 1 d . . . . .
C12 C 0.3390(4) 0.4478(2) 0.5267(3) 0.0404(9) Uani 1 1 d . . . . .
H12 H 0.292404 0.428620 0.473894 0.048 Uiso 1 1 calc R U . . .
C13 C 0.4448(4) 0.3957(2) 0.5750(3) 0.0412(9) Uani 1 1 d . . . . .
H13 H 0.466534 0.340494 0.556217 0.049 Uiso 1 1 calc R U . . .
C14 C 0.5219(4) 0.4247(2) 0.6536(3) 0.0370(8) Uani 1 1 d . . . . .
C15 C 0.6380(4) 0.3762(2) 0.7082(3) 0.0452(10) Uani 1 1 d . . . . .
C16 C 0.7049(4) 0.4147(3) 0.7820(3) 0.0494(10) Uani 1 1 d . . . . .
H16 H 0.778051 0.382336 0.818576 0.059 Uiso 1 1 calc R U . . .
C17 C 0.6711(4) 0.4995(3) 0.8065(3) 0.0489(10) Uani 1 1 d . . . . .
C18 C 0.5592(4) 0.5484(2) 0.7529(3) 0.0401(9) Uani 1 1 d . . . . .
C19 C 0.4814(4) 0.5094(2) 0.6783(2) 0.0341(8) Uani 1 1 d . . . . .
C20 C 0.1829(4) 0.5867(2) 0.4995(3) 0.0462(9) Uani 1 1 d . . . . .
H20A H 0.186341 0.572446 0.441829 0.069 Uiso 1 1 calc R U . . .
H20B H 0.211978 0.646531 0.509153 0.069 Uiso 1 1 calc R U . . .
H20C H 0.076009 0.577370 0.511817 0.069 Uiso 1 1 calc R U . . .
C21 C 0.6836(5) 0.2856(2) 0.6852(3) 0.0555(12) Uani 1 1 d . . . . .
H21A H 0.590720 0.248596 0.680731 0.083 Uiso 1 1 calc R U . . .
H21B H 0.765877 0.263524 0.727761 0.083 Uiso 1 1 calc R U . . .
H21C H 0.723171 0.286887 0.632411 0.083 Uiso 1 1 calc R U . . .
C22 C 0.7479(5) 0.5371(3) 0.8885(3) 0.0715(13) Uani 1 1 d . . . . .
H22A H 0.796330 0.491442 0.924182 0.107 Uiso 1 1 calc R U . . .
H22B H 0.667635 0.565865 0.914993 0.107 Uiso 1 1 calc R U . . .
H22C H 0.829090 0.578185 0.878827 0.107 Uiso 1 1 calc R U . . .
Cl1 Cl 0.52300(12) 0.73477(7) 0.60322(7) 0.0550(3) Uani 1 1 d . . . . .
Ir1 Ir 0.33240(2) 0.68128(2) 0.68806(2) 0.03424(5) Uani 1 1 d . . . . .
N1 N 0.3659(3) 0.55988(16) 0.62941(19) 0.0319(6) Uani 1 1 d . . . . .
O1 O 0.5242(3) 0.63008(17) 0.76927(18) 0.0465(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.445(6) . ?
C1 C5 1.424(6) . ?
C1 C6 1.499(5) . ?
C1 Ir1 2.131(4) . ?
C2 C3 1.434(6) . ?
C2 C7 1.490(6) . ?
C2 Ir1 2.128(4) . ?
C3 C4 1.433(5) . ?
C3 C8 1.507(5) . ?
C3 Ir1 2.155(3) . ?
C4 C5 1.432(5) . ?
C4 C9 1.499(6) . ?
C4 Ir1 2.190(3) . ?
C5 C10 1.498(6) . ?
C5 Ir1 2.175(3) . ?
C11 C12 1.415(4) . ?
C11 C20 1.482(5) . ?
C11 N1 1.336(4) . ?
C12 C13 1.355(5) . ?
C13 C14 1.406(5) . ?
C14 C15 1.424(5) . ?
C14 C19 1.421(5) . ?
C15 C16 1.373(6) . ?
C15 C21 1.509(5) . ?
C16 C17 1.406(6) . ?
C17 C18 1.397(5) . ?
C17 C22 1.498(6) . ?
C18 C19 1.413(5) . ?
C18 O1 1.328(4) . ?
C19 N1 1.392(4) . ?
Cl1 Ir1 2.4046(10) . ?
Ir1 N1 2.134(3) . ?
Ir1 O1 2.073(2) . ?

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 C6 125.6(4) . . ?
C2 C1 Ir1 70.0(2) . . ?
C5 C1 C2 108.0(3) . . ?
C5 C1 C6 126.4(4) . . ?
C5 C1 Ir1 72.4(2) . . ?
C6 C1 Ir1 123.1(3) . . ?
C1 C2 C7 125.4(4) . . ?
C1 C2 Ir1 70.3(2) . . ?
C3 C2 C1 106.9(4) . . ?
C3 C2 C7 127.6(4) . . ?
C3 C2 Ir1 71.5(2) . . ?
C7 C2 Ir1 125.6(3) . . ?
C2 C3 C8 125.6(4) . . ?
C2 C3 Ir1 69.4(2) . . ?
C4 C3 C2 109.1(3) . . ?
C4 C3 C8 125.2(4) . . ?
C4 C3 Ir1 72.1(2) . . ?
C8 C3 Ir1 126.8(3) . . ?
C3 C4 C9 126.7(4) . . ?
C3 C4 Ir1 69.42(19) . . ?
C5 C4 C3 107.0(4) . . ?
C5 C4 C9 125.0(4) . . ?
C5 C4 Ir1 70.3(2) . . ?
C9 C4 Ir1 135.5(3) . . ?
C1 C5 C4 109.0(4) . . ?
C1 C5 C10 125.9(4) . . ?
C1 C5 Ir1 69.0(2) . . ?
C4 C5 C10 125.1(5) . . ?
C4 C5 Ir1 71.43(19) . . ?
C10 C5 Ir1 126.2(3) . . ?
C12 C11 C20 120.3(3) . . ?
N1 C11 C12 119.8(3) . . ?
N1 C11 C20 119.9(3) . . ?
C13 C12 C11 121.7(4) . . ?
C12 C13 C14 120.2(3) . . ?
C13 C14 C15 124.8(3) . . ?
C13 C14 C19 116.6(3) . . ?
C19 C14 C15 118.6(4) . . ?
C14 C15 C21 120.6(4) . . ?
C16 C15 C14 117.6(3) . . ?
C16 C15 C21 121.8(4) . . ?
C15 C16 C17 124.8(4) . . ?
C16 C17 C22 121.9(4) . . ?
C18 C17 C16 118.2(4) . . ?
C18 C17 C22 119.9(4) . . ?
C17 C18 C19 118.7(3) . . ?
O1 C18 C17 122.4(4) . . ?
O1 C18 C19 118.9(3) . . ?
C18 C19 C14 122.0(3) . . ?
N1 C19 C14 122.0(3) . . ?
N1 C19 C18 116.0(3) . . ?
C1 Ir1 C3 65.33(14) . . ?
C1 Ir1 C4 65.07(15) . . ?
C1 Ir1 C5 38.60(17) . . ?
C1 Ir1 Cl1 113.04(12) . . ?
C1 Ir1 N1 161.22(15) . . ?
C2 Ir1 C1 39.67(15) . . ?
C2 Ir1 C3 39.12(15) . . ?
C2 Ir1 C4 65.47(16) . . ?
C2 Ir1 C5 65.27(16) . . ?
C2 Ir1 Cl1 152.52(11) . . ?
C2 Ir1 N1 122.23(13) . . ?
C3 Ir1 C4 38.49(14) . . ?
C3 Ir1 C5 64.24(14) . . ?
C3 Ir1 Cl1 148.72(12) . . ?
C4 Ir1 Cl1 110.81(12) . . ?
C5 Ir1 C4 38.30(14) . . ?
C5 Ir1 Cl1 94.57(11) . . ?
N1 Ir1 C3 103.49(12) . . ?
N1 Ir1 C4 116.40(12) . . ?
N1 Ir1 C5 152.00(14) . . ?
N1 Ir1 Cl1 84.47(7) . . ?
O1 Ir1 C1 94.51(14) . . ?
O1 Ir1 C2 90.83(13) . . ?
O1 Ir1 C3 122.87(14) . . ?
O1 Ir1 C4 155.98(14) . . ?
O1 Ir1 C5 129.27(14) . . ?
O1 Ir1 Cl1 88.22(8) . . ?
O1 Ir1 N1 78.73(10) . . ?
C11 N1 C19 119.6(3) . . ?
C11 N1 Ir1 128.9(2) . . ?
C19 N1 Ir1 111.4(2) . . ?
C18 O1 Ir1 114.2(2) . . ?

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 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C8 -177.0(3) . . . . ?
C1 C2 C3 Ir1 61.7(2) . . . . ?
C2 C1 C5 C4 -0.8(4) . . . . ?
C2 C1 C5 C10 178.4(4) . . . . ?
C2 C1 C5 Ir1 -61.3(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C2 C3 C4 C9 -168.1(4) . . . . ?
C2 C3 C4 Ir1 59.8(2) . . . . ?
C3 C4 C5 C1 1.0(4) . . . . ?
C3 C4 C5 C10 -178.3(4) . . . . ?
C3 C4 C5 Ir1 60.0(2) . . . . ?
C5 C1 C2 C3 0.3(4) . . . . ?
C5 C1 C2 C7 -177.0(4) . . . . ?
C5 C1 C2 Ir1 62.8(3) . . . . ?
C6 C1 C2 C3 -179.5(3) . . . . ?
C6 C1 C2 C7 3.2(6) . . . . ?
C6 C1 C2 Ir1 -117.1(4) . . . . ?
C6 C1 C5 C4 179.1(3) . . . . ?
C6 C1 C5 C10 -1.7(6) . . . . ?
C6 C1 C5 Ir1 118.6(4) . . . . ?
C7 C2 C3 C4 177.5(4) . . . . ?
C7 C2 C3 C8 0.2(6) . . . . ?
C7 C2 C3 Ir1 -121.1(4) . . . . ?
C8 C3 C4 C5 176.5(3) . . . . ?
C8 C3 C4 C9 9.2(6) . . . . ?
C8 C3 C4 Ir1 -122.9(4) . . . . ?
C9 C4 C5 C1 168.6(4) . . . . ?
C9 C4 C5 C10 -10.6(6) . . . . ?
C9 C4 C5 Ir1 -132.4(4) . . . . ?
C11 C12 C13 C14 -2.6(5) . . . . ?
C12 C11 N1 C19 2.3(4) . . . . ?
C12 C11 N1 Ir1 179.1(2) . . . . ?
C12 C13 C14 C15 -178.2(3) . . . . ?
C12 C13 C14 C19 0.6(5) . . . . ?
C13 C14 C15 C16 178.5(3) . . . . ?
C13 C14 C15 C21 -2.0(5) . . . . ?
C13 C14 C19 C18 -175.3(3) . . . . ?
C13 C14 C19 N1 2.9(5) . . . . ?
C14 C15 C16 C17 -2.1(6) . . . . ?
C14 C19 N1 C11 -4.4(4) . . . . ?
C14 C19 N1 Ir1 178.3(2) . . . . ?
C15 C14 C19 C18 3.6(5) . . . . ?
C15 C14 C19 N1 -178.2(3) . . . . ?
C15 C16 C17 C18 1.2(6) . . . . ?
C15 C16 C17 C22 179.5(4) . . . . ?
C16 C17 C18 C19 2.2(5) . . . . ?
C16 C17 C18 O1 -177.4(3) . . . . ?
C17 C18 C19 C14 -4.6(5) . . . . ?
C17 C18 C19 N1 177.2(3) . . . . ?
C17 C18 O1 Ir1 -172.0(3) . . . . ?
C18 C19 N1 C11 173.9(3) . . . . ?
C18 C19 N1 Ir1 -3.4(3) . . . . ?
C19 C14 C15 C16 -0.2(5) . . . . ?
C19 C14 C15 C21 179.3(3) . . . . ?
C19 C18 O1 Ir1 8.4(4) . . . . ?
C20 C11 C12 C13 179.3(3) . . . . ?
C20 C11 N1 C19 -175.8(3) . . . . ?
C20 C11 N1 Ir1 1.0(4) . . . . ?
C21 C15 C16 C17 178.4(4) . . . . ?
C22 C17 C18 C19 -176.2(4) . . . . ?
C22 C17 C18 O1 4.2(6) . . . . ?
Ir1 C1 C2 C3 -62.5(2) . . . . ?
Ir1 C1 C2 C7 120.2(4) . . . . ?
Ir1 C1 C5 C4 60.5(2) . . . . ?
Ir1 C1 C5 C10 -120.2(4) . . . . ?
Ir1 C2 C3 C4 -61.5(2) . . . . ?
Ir1 C2 C3 C8 121.2(4) . . . . ?
Ir1 C3 C4 C5 -60.6(2) . . . . ?
Ir1 C3 C4 C9 132.1(4) . . . . ?
Ir1 C4 C5 C1 -59.0(2) . . . . ?
Ir1 C4 C5 C10 121.7(4) . . . . ?
N1 C11 C12 C13 1.2(5) . . . . ?
O1 C18 C19 C14 175.1(3) . . . . ?
O1 C18 C19 N1 -3.2(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'placed on a MiTeGen micromount'
_olex2_submission_original_sample_id LB483
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.159
_oxdiff_exptl_absorpt_empirical_full_min 0.908
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_03664_amarillo
_database_code_depnum_ccdc_archive 'CCDC 2466572'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles Hernaez '
;Laboratorio DRX Monocristal, SIdI, Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2026-05-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            AU-144_250K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21.75 H28.50 Cl2.50 Ir N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         648.78

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6976(5)
_cell_length_b                   10.0918(3)
_cell_length_c                   17.0571(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.1168(13)
_cell_angle_gamma                90
_cell_volume                     2526.26(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.7588
_cell_measurement_theta_max      23.9422
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.022
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1270

_exptl_absorpt_coefficient_mu    5.575
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            74839
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             4608
_reflns_number_gt                3783
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0826
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         4608
_refine_ls_number_parameters     287
_refine_ls_number_restraints     336
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+10.4132P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.231
_refine_diff_density_min         -0.761
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4791(4) 0.4623(6) 0.1705(4) 0.0421(14) Uani d . . . 1.000000 . .
C C2 0.5716(4) 0.4183(6) 0.1806(4) 0.0380(13) Uani d . . . 1.000000 . .
C C3 0.6268(4) 0.4957(6) 0.1314(3) 0.0371(13) Uani d . . . 1.000000 . .
C C4 0.5670(5) 0.5875(6) 0.0887(3) 0.0414(13) Uani d . . . 1.000000 . .
C C5 0.4765(5) 0.5689(7) 0.1132(4) 0.0430(14) Uani d . . . 1.000000 . .
C C6 0.3991(5) 0.4060(9) 0.2099(5) 0.067(2) Uani d . . . 1.000000 . .
H H6A 0.367985 0.342395 0.175261 0.101000 Uiso calc U . R 1.000000 . .
H H6B 0.357441 0.476911 0.221753 0.101000 Uiso calc U . R 1.000000 . .
H H6C 0.420003 0.362250 0.258214 0.101000 Uiso calc U . R 1.000000 . .
C C7 0.6039(6) 0.3056(7) 0.2326(4) 0.0573(19) Uani d . . . 1.000000 . .
H H7A 0.591397 0.222220 0.205842 0.086000 Uiso calc U . R 1.000000 . .
H H7B 0.572176 0.307870 0.280984 0.086000 Uiso calc U . R 1.000000 . .
H H7C 0.668905 0.314039 0.244479 0.086000 Uiso calc U . R 1.000000 . .
C C8 0.7270(5) 0.4761(8) 0.1201(4) 0.059(2) Uani d . . . 1.000000 . .
H H8A 0.734560 0.414967 0.077094 0.088000 Uiso calc U . R 1.000000 . .
H H8B 0.756271 0.440211 0.167843 0.088000 Uiso calc U . R 1.000000 . .
H H8C 0.754542 0.560560 0.108167 0.088000 Uiso calc U . R 1.000000 . .
C C9 0.5956(6) 0.6863(8) 0.0299(4) 0.065(2) Uani d . . . 1.000000 . .
H H9A 0.586117 0.649619 -0.022490 0.098000 Uiso calc U . R 1.000000 . .
H H9B 0.659572 0.707232 0.039839 0.098000 Uiso calc U . R 1.000000 . .
H H9C 0.559589 0.766326 0.034018 0.098000 Uiso calc U . R 1.000000 . .
C C10 0.3924(6) 0.6404(9) 0.0849(5) 0.074(3) Uani d . . . 1.000000 . .
H H10A 0.360350 0.588763 0.044161 0.111000 Uiso calc U . R 1.000000 . .
H H10B 0.408714 0.725953 0.063863 0.111000 Uiso calc U . R 1.000000 . .
H H10C 0.353273 0.653160 0.128299 0.111000 Uiso calc U . R 1.000000 . .
C C11 0.7081(4) 0.5609(6) 0.3444(4) 0.0394(14) Uani d . . . 1.000000 . .
H H11 0.740700 0.522953 0.304119 0.047000 Uiso calc U . R 1.000000 . .
C C12 0.7446(4) 0.5554(7) 0.4196(4) 0.0431(15) Uani d . . . 1.000000 . .
H H12 0.801949 0.516626 0.430735 0.052000 Uiso calc U . R 1.000000 . .
C C13 0.6952(4) 0.6083(6) 0.4795(4) 0.0384(13) Uani d . . . 1.000000 . .
H H13 0.717721 0.602105 0.531985 0.046000 Uiso calc U . R 1.000000 . .
C C14 0.6130(4) 0.6699(5) 0.4611(3) 0.0294(11) Uani d . . . 1.000000 . .
C C15 0.5549(4) 0.7268(6) 0.5243(3) 0.0376(13) Uani d . . . 1.000000 . .
C C16 0.4562(4) 0.7321(6) 0.4966(4) 0.0400(13) Uani d . . . 1.000000 . .
H H16 0.414861 0.770021 0.534657 0.048000 Uiso calc U . R 1.000000 . .
C C17 0.4250(4) 0.7455(5) 0.4139(3) 0.0327(12) Uani d . . . 1.000000 . .
C C18 0.4977(4) 0.7508(5) 0.3539(3) 0.0280(11) Uani d . . . 1.000000 . .
C C19 0.5825(4) 0.6753(5) 0.3834(3) 0.0278(11) Uani d . . . 1.000000 . .
C C20 0.5881(5) 0.8653(6) 0.5476(4) 0.0499(16) Uani d . . . 1.000000 . .
H H20A 0.587370 0.921364 0.501429 0.075000 Uiso calc U . R 1.000000 . .
H H20B 0.649677 0.859936 0.570899 0.075000 Uiso calc U . R 1.000000 . .
H H20C 0.548262 0.902625 0.585439 0.075000 Uiso calc U . R 1.000000 . .
C C21 0.3343(4) 0.8028(7) 0.3894(4) 0.0438(15) Uani d . . . 1.000000 . .
H H21A 0.340293 0.897607 0.381923 0.066000 Uiso calc U . R 1.000000 . .
H H21B 0.291793 0.785887 0.429785 0.066000 Uiso calc U . R 1.000000 . .
H H21C 0.311925 0.762101 0.340585 0.066000 Uiso calc U . R 1.000000 . .
Cl Cl1 0.63022(11) 0.84027(17) 0.20388(9) 0.0465(4) Uani d . . . 1.000000 . .
Ir Ir1 0.56207(2) 0.62292(2) 0.21340(2) 0.02766(9) Uani d . . . 1.000000 . .
N N1 0.6279(3) 0.6182(4) 0.3258(3) 0.0293(10) Uani d . . . 1.000000 . .
O O1 0.4657(2) 0.7050(4) 0.2828(2) 0.0294(8) Uani d . . . 1.000000 . .
O O2 0.5216(3) 0.8893(3) 0.3522(2) 0.0343(9) Uani d . . . 1.000000 . .
H H2O 0.557489 0.902282 0.317083 0.041000 Uiso calc U . R 1.000000 . .
O O3 0.4210(3) 0.6179(4) 0.4537(3) 0.0417(10) Uani d . . . 1.000000 . .
O O4 0.5641(4) 0.6490(5) 0.5938(2) 0.0539(12) Uani d . . . 1.000000 . .
H H4O 0.549686 0.571220 0.583405 0.065000 Uiso calc U . R 1.000000 . .
C C22 0.4115(7) 0.9849(10) 0.1858(5) 0.056(2) Uani d U P . 0.750000 . .
H H22A 0.434985 0.895837 0.197527 0.068000 Uiso calc U P R 0.750000 A 1
H H22B 0.438033 1.046104 0.225363 0.068000 Uiso calc U P R 0.750000 A 1
Cl Cl2 0.4414(2) 1.0334(4) 0.09272(18) 0.0905(9) Uani d U P . 0.750000 B .
Cl Cl3A 0.2966(3) 0.9858(5) 0.1881(2) 0.0905(9) Uani d U P . 0.627(5) B 1
Cl Cl3B 0.3217(15) 1.067(3) 0.2336(13) 0.0905(9) Uani d U P . 0.123(5) B 2


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.432(9) ?
C1 C5 . 1.453(10) ?
C1 C6 . 1.497(10) ?
C1 Ir1 . 2.134(6) ?
C2 C3 . 1.431(9) ?
C2 C7 . 1.503(9) ?
C2 Ir1 . 2.146(6) ?
C3 C4 . 1.447(9) ?
C3 C8 . 1.508(9) ?
C3 Ir1 . 2.157(6) ?
C4 C5 . 1.428(9) ?
C4 C9 . 1.491(9) ?
C4 Ir1 . 2.162(6) ?
C5 C10 . 1.489(10) ?
C5 Ir1 . 2.137(6) ?
C11 N1 . 1.336(7) ?
C11 C12 . 1.364(8) ?
C12 C13 . 1.390(9) ?
C13 C14 . 1.381(8) ?
C14 C19 . 1.377(7) ?
C14 C15 . 1.524(8) ?
C15 O4 . 1.421(7) ?
C15 C16 . 1.502(9) ?
C15 C20 . 1.526(9) ?
C16 O3 . 1.446(7) ?
C16 C17 . 1.465(8) ?
C17 O3 . 1.458(7) ?
C17 C21 . 1.492(8) ?
C17 C18 . 1.520(7) ?
C18 O1 . 1.359(6) ?
C18 O2 . 1.442(6) ?
C18 C19 . 1.522(7) ?
C19 N1 . 1.346(7) ?
Cl1 Ir1 . 2.4204(15) ?
Ir1 O1 . 2.068(4) ?
Ir1 N1 . 2.101(4) ?
C22 Cl3A . 1.691(11) ?
C22 Cl2 . 1.740(9) ?
C22 Cl3B . 1.79(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C5 . . 107.5(6) ?
C2 C1 C6 . . 126.3(7) ?
C5 C1 C6 . . 126.2(6) ?
C2 C1 Ir1 . . 70.9(3) ?
C5 C1 Ir1 . . 70.2(3) ?
C6 C1 Ir1 . . 125.6(5) ?
C3 C2 C1 . . 109.0(6) ?
C3 C2 C7 . . 126.0(6) ?
C1 C2 C7 . . 125.0(6) ?
C3 C2 Ir1 . . 71.0(3) ?
C1 C2 Ir1 . . 70.0(3) ?
C7 C2 Ir1 . . 126.7(5) ?
C2 C3 C4 . . 107.2(5) ?
C2 C3 C8 . . 126.3(6) ?
C4 C3 C8 . . 126.2(6) ?
C2 C3 Ir1 . . 70.2(3) ?
C4 C3 Ir1 . . 70.6(3) ?
C8 C3 Ir1 . . 129.0(4) ?
C5 C4 C3 . . 108.6(6) ?
C5 C4 C9 . . 125.8(6) ?
C3 C4 C9 . . 125.6(7) ?
C5 C4 Ir1 . . 69.7(3) ?
C3 C4 Ir1 . . 70.3(3) ?
C9 C4 Ir1 . . 125.3(5) ?
C4 C5 C1 . . 107.7(6) ?
C4 C5 C10 . . 127.7(7) ?
C1 C5 C10 . . 124.6(7) ?
C4 C5 Ir1 . . 71.5(3) ?
C1 C5 Ir1 . . 70.0(3) ?
C10 C5 Ir1 . . 125.2(5) ?
N1 C11 C12 . . 122.5(6) ?
C11 C12 C13 . . 118.8(6) ?
C14 C13 C12 . . 119.4(5) ?
C19 C14 C13 . . 118.2(5) ?
C19 C14 C15 . . 120.1(5) ?
C13 C14 C15 . . 121.7(5) ?
O4 C15 C16 . . 109.2(5) ?
O4 C15 C14 . . 110.5(5) ?
C16 C15 C14 . . 111.0(5) ?
O4 C15 C20 . . 105.9(5) ?
C16 C15 C20 . . 109.8(5) ?
C14 C15 C20 . . 110.3(5) ?
O3 C16 C17 . . 60.1(4) ?
O3 C16 C15 . . 116.4(5) ?
C17 C16 C15 . . 123.5(5) ?
O3 C17 C16 . . 59.3(4) ?
O3 C17 C21 . . 114.5(5) ?
C16 C17 C21 . . 122.3(5) ?
O3 C17 C18 . . 113.1(4) ?
C16 C17 C18 . . 117.2(5) ?
C21 C17 C18 . . 116.6(5) ?
O1 C18 O2 . . 112.6(4) ?
O1 C18 C17 . . 111.6(5) ?
O2 C18 C17 . . 103.2(4) ?
O1 C18 C19 . . 111.2(4) ?
O2 C18 C19 . . 107.2(4) ?
C17 C18 C19 . . 110.7(4) ?
N1 C19 C14 . . 122.4(5) ?
N1 C19 C18 . . 113.8(5) ?
C14 C19 C18 . . 123.7(5) ?
O1 Ir1 N1 . . 77.45(15) ?
O1 Ir1 C1 . . 95.9(2) ?
N1 Ir1 C1 . . 121.4(2) ?
O1 Ir1 C5 . . 99.7(2) ?
N1 Ir1 C5 . . 161.1(2) ?
C1 Ir1 C5 . . 39.8(3) ?
O1 Ir1 C2 . . 126.2(2) ?
N1 Ir1 C2 . . 100.5(2) ?
C1 Ir1 C2 . . 39.1(2) ?
C5 Ir1 C2 . . 65.8(2) ?
O1 Ir1 C3 . . 161.7(2) ?
N1 Ir1 C3 . . 112.4(2) ?
C1 Ir1 C3 . . 65.8(2) ?
C5 Ir1 C3 . . 65.9(2) ?
C2 Ir1 C3 . . 38.9(2) ?
O1 Ir1 C4 . . 133.6(2) ?
N1 Ir1 C4 . . 148.8(2) ?
C1 Ir1 C4 . . 65.6(3) ?
C5 Ir1 C4 . . 38.8(2) ?
C2 Ir1 C4 . . 65.1(2) ?
C3 Ir1 C4 . . 39.1(2) ?
O1 Ir1 Cl1 . . 88.53(11) ?
N1 Ir1 Cl1 . . 84.85(13) ?
C1 Ir1 Cl1 . . 153.70(19) ?
C5 Ir1 Cl1 . . 113.9(2) ?
C2 Ir1 Cl1 . . 145.24(18) ?
C3 Ir1 Cl1 . . 107.28(17) ?
C4 Ir1 Cl1 . . 92.72(18) ?
C11 N1 C19 . . 118.6(5) ?
C11 N1 Ir1 . . 125.6(4) ?
C19 N1 Ir1 . . 115.7(4) ?
C18 O1 Ir1 . . 115.6(3) ?
C16 O3 C17 . . 60.6(4) ?
Cl3A C22 Cl2 . . 108.8(5) ?
Cl2 C22 Cl3B . . 120.8(8) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 C1 C2 C3 . . . . 0.6(7) ?
C6 C1 C2 C3 . . . . 178.7(6) ?
Ir1 C1 C2 C3 . . . . -60.5(4) ?
C5 C1 C2 C7 . . . . -177.5(6) ?
C6 C1 C2 C7 . . . . 0.7(10) ?
Ir1 C1 C2 C7 . . . . 121.4(6) ?
C5 C1 C2 Ir1 . . . . 61.1(4) ?
C6 C1 C2 Ir1 . . . . -120.7(6) ?
C1 C2 C3 C4 . . . . -1.3(7) ?
C7 C2 C3 C4 . . . . 176.8(6) ?
Ir1 C2 C3 C4 . . . . -61.2(4) ?
C1 C2 C3 C8 . . . . -175.7(6) ?
C7 C2 C3 C8 . . . . 2.4(10) ?
Ir1 C2 C3 C8 . . . . 124.4(6) ?
C1 C2 C3 Ir1 . . . . 59.9(4) ?
C7 C2 C3 Ir1 . . . . -122.0(6) ?
C2 C3 C4 C5 . . . . 1.6(7) ?
C8 C3 C4 C5 . . . . 176.0(6) ?
Ir1 C3 C4 C5 . . . . -59.3(4) ?
C2 C3 C4 C9 . . . . -179.2(6) ?
C8 C3 C4 C9 . . . . -4.8(10) ?
Ir1 C3 C4 C9 . . . . 119.9(7) ?
C2 C3 C4 Ir1 . . . . 60.9(4) ?
C8 C3 C4 Ir1 . . . . -124.7(6) ?
C3 C4 C5 C1 . . . . -1.2(7) ?
C9 C4 C5 C1 . . . . 179.5(6) ?
Ir1 C4 C5 C1 . . . . -61.0(4) ?
C3 C4 C5 C10 . . . . -179.6(6) ?
C9 C4 C5 C10 . . . . 1.2(11) ?
Ir1 C4 C5 C10 . . . . 120.7(7) ?
C3 C4 C5 Ir1 . . . . 59.7(4) ?
C9 C4 C5 Ir1 . . . . -119.5(7) ?
C2 C1 C5 C4 . . . . 0.4(7) ?
C6 C1 C5 C4 . . . . -177.8(6) ?
Ir1 C1 C5 C4 . . . . 61.9(4) ?
C2 C1 C5 C10 . . . . 178.8(6) ?
C6 C1 C5 C10 . . . . 0.6(10) ?
Ir1 C1 C5 C10 . . . . -119.7(6) ?
C2 C1 C5 Ir1 . . . . -61.5(4) ?
C6 C1 C5 Ir1 . . . . 120.3(6) ?
N1 C11 C12 C13 . . . . 1.8(10) ?
C11 C12 C13 C14 . . . . -2.9(10) ?
C12 C13 C14 C19 . . . . 0.7(9) ?
C12 C13 C14 C15 . . . . 178.5(6) ?
C19 C14 C15 O4 . . . . 144.5(6) ?
C13 C14 C15 O4 . . . . -33.4(8) ?
C19 C14 C15 C16 . . . . 23.1(7) ?
C13 C14 C15 C16 . . . . -154.7(6) ?
C19 C14 C15 C20 . . . . -98.8(6) ?
C13 C14 C15 C20 . . . . 83.4(7) ?
O4 C15 C16 O3 . . . . -79.9(6) ?
C14 C15 C16 O3 . . . . 42.3(7) ?
C20 C15 C16 O3 . . . . 164.5(5) ?
O4 C15 C16 C17 . . . . -150.1(5) ?
C14 C15 C16 C17 . . . . -28.0(8) ?
C20 C15 C16 C17 . . . . 94.2(7) ?
C15 C16 C17 O3 . . . . 103.5(6) ?
O3 C16 C17 C21 . . . . 101.2(6) ?
C15 C16 C17 C21 . . . . -155.3(6) ?
O3 C16 C17 C18 . . . . -102.0(5) ?
C15 C16 C17 C18 . . . . 1.6(8) ?
O3 C17 C18 O1 . . . . 86.7(6) ?
C16 C17 C18 O1 . . . . 152.8(5) ?
C21 C17 C18 O1 . . . . -49.1(7) ?
O3 C17 C18 O2 . . . . -152.2(4) ?
C16 C17 C18 O2 . . . . -86.1(6) ?
C21 C17 C18 O2 . . . . 72.0(6) ?
O3 C17 C18 C19 . . . . -37.8(6) ?
C16 C17 C18 C19 . . . . 28.3(7) ?
C21 C17 C18 C19 . . . . -173.5(5) ?
C13 C14 C19 N1 . . . . 2.8(8) ?
C15 C14 C19 N1 . . . . -175.1(5) ?
C13 C14 C19 C18 . . . . -174.2(5) ?
C15 C14 C19 C18 . . . . 7.9(8) ?
O1 C18 C19 N1 . . . . 23.6(6) ?
O2 C18 C19 N1 . . . . -99.9(5) ?
C17 C18 C19 N1 . . . . 148.3(5) ?
O1 C18 C19 C14 . . . . -159.1(5) ?
O2 C18 C19 C14 . . . . 77.4(6) ?
C17 C18 C19 C14 . . . . -34.5(7) ?
C12 C11 N1 C19 . . . . 1.6(9) ?
C12 C11 N1 Ir1 . . . . -176.4(5) ?
C14 C19 N1 C11 . . . . -4.0(8) ?
C18 C19 N1 C11 . . . . 173.3(5) ?
C14 C19 N1 Ir1 . . . . 174.2(4) ?
C18 C19 N1 Ir1 . . . . -8.5(6) ?
O2 C18 O1 Ir1 . . . . 92.4(4) ?
C17 C18 O1 Ir1 . . . . -152.1(3) ?
C19 C18 O1 Ir1 . . . . -27.9(5) ?
C15 C16 O3 C17 . . . . -115.2(6) ?
C21 C17 O3 C16 . . . . -114.3(6) ?
C18 C17 O3 C16 . . . . 108.9(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C11 H11 Cl1 2_645 0.94 2.65 3.390(6) 135.6 ?
C20 H20C O2 3_676 0.97 2.59 3.457(7) 148.7 ?
C21 H21C Cl3B^b 2_545 0.97 3.01 3.84(2) 145.2 ?
O2 H2O Cl1 . 0.83 2.34 3.104(4) 152.8 ?
O4 H4O O3 3_666 0.83 2.06 2.825(6) 152.3 ?
C22 H22A^a Cl1 . 0.98 2.92 3.529(10) 121.2 ?
C22 H22A^a O1 . 0.98 2.44 3.348(10) 153.9 ?

