# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_230131_irtpyclanpf6
_database_code_depnum_ccdc_archive 'CCDC 2302205'
loop_
_audit_author_name
_audit_author_address
'SEIJI OGO'
;Kyushu University
Japan
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        Ir2tpy2Cl2AN2PF6
_chemical_formula_moiety         'C17 H14 Cl Ir N4, F6 P, C2 H3 N'
_chemical_formula_sum            'C19 H17 Cl F6 Ir N5 P'
_chemical_formula_weight         687.99
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ir2 C30 H22 N6 Cl2 P2 F12'
_chemical_oxdiff_usercomment     AN_Et2O
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.0860(12)
_cell_length_b                   12.9848(9)
_cell_length_c                   25.954(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.818(10)
_cell_angle_gamma                90
_cell_volume                     4357.9(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3086
_cell_measurement_temperature    143
_cell_measurement_theta_max      27.0930
_cell_measurement_theta_min      3.1360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.393
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.097
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2632
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15271
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.589
_diffrn_reflns_theta_min         2.588
_diffrn_ambient_temperature      143
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00   2.00   0.50  100.00    --    5.00  28.00 -60.00   54
  2  ω     -7.00  29.00   0.50  100.00    --  -12.30  46.00   0.00   72
  3  ω    -74.00  74.00   0.50  100.00    --  -12.30  55.00  60.00  296
  4  ω   -100.00 -17.00   0.50  100.00    --  -12.30  46.00   0.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0443020000
_diffrn_orient_matrix_UB_12      0.0320796000
_diffrn_orient_matrix_UB_13      0.0040667000
_diffrn_orient_matrix_UB_21      0.0306463000
_diffrn_orient_matrix_UB_22      -0.0426288000
_diffrn_orient_matrix_UB_23      0.0100970000
_diffrn_orient_matrix_UB_31      0.0101875000
_diffrn_orient_matrix_UB_32      -0.0117837000
_diffrn_orient_matrix_UB_33      -0.0254250000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3671
_reflns_number_total             5196
_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 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.413
_refine_diff_density_min         -1.362
_refine_diff_density_rms         0.209
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+53.8470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0976
_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:
 C1(H1), C8(H8), C4(H4), C15(H15), C7(H7), C3(H3), C2(H2), C14(H14), C9(H9),
 C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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
Ir1 Ir 0.64463(2) 0.28941(2) 0.48655(2) 0.01766(9) Uani 1 1 d . . . . .
Cl1 Cl 0.45413(14) 0.30487(14) 0.46131(8) 0.0280(5) Uani 1 1 d . . . . .
P1 P 0.6302(2) 0.47607(19) 0.26618(10) 0.0408(6) Uani 1 1 d . . . . .
N4 N 0.6573(5) 0.4314(5) 0.4569(3) 0.0214(14) Uani 1 1 d . . . . .
N2 N 0.6298(5) 0.1524(4) 0.5155(3) 0.0208(14) Uani 1 1 d . . . . .
N1 N 0.6226(5) 0.3302(5) 0.5602(3) 0.0266(15) Uani 1 1 d . . . . .
N3 N 0.6498(5) 0.2020(5) 0.4212(3) 0.0260(15) Uani 1 1 d . . . . .
C5 C 0.6085(6) 0.2459(7) 0.5909(4) 0.031(2) Uani 1 1 d . . . . .
C6 C 0.6152(6) 0.1449(7) 0.5659(4) 0.031(2) Uani 1 1 d . . . . .
C17 C 0.6711(7) 0.6185(6) 0.4231(4) 0.037(2) Uani 1 1 d . . . . .
H17A H 0.652133 0.618271 0.385048 0.056 Uiso 1 1 calc R U . . .
H17B H 0.742503 0.642476 0.432382 0.056 Uiso 1 1 calc R U . . .
H17C H 0.624600 0.664609 0.438386 0.056 Uiso 1 1 calc R U . . .
C1 C 0.6108(6) 0.4235(7) 0.5794(4) 0.032(2) Uani 1 1 d . . . . .
H1 H 0.615806 0.481242 0.557447 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6141(6) -0.0376(7) 0.5570(4) 0.037(2) Uani 1 1 d . . . . .
H8 H 0.611755 -0.104152 0.572027 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6620(6) 0.5139(6) 0.4431(4) 0.0307(19) Uani 1 1 d . . . . .
C11 C 0.6392(5) 0.0980(6) 0.4299(3) 0.0258(19) Uani 1 1 d . . . . .
C4 C 0.5888(7) 0.2590(8) 0.6410(4) 0.041(2) Uani 1 1 d . . . . .
H4 H 0.580649 0.200855 0.662289 0.050 Uiso 1 1 calc R U . . .
F4 F 0.6112(9) 0.4918(7) 0.2076(3) 0.127(4) Uani 1 1 d . . . . .
C10 C 0.6319(6) 0.0699(6) 0.4845(4) 0.0273(18) Uani 1 1 d . . . . .
C15 C 0.6545(6) 0.2333(7) 0.3723(4) 0.036(2) Uani 1 1 d . . . . .
H15 H 0.660210 0.304833 0.365679 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6080(6) 0.0471(7) 0.5874(4) 0.037(2) Uani 1 1 d . . . . .
H7 H 0.598882 0.039669 0.622783 0.044 Uiso 1 1 calc R U . . .
C3 C 0.5810(7) 0.3571(8) 0.6601(4) 0.044(2) Uani 1 1 d . . . . .
H3 H 0.568180 0.366533 0.694870 0.053 Uiso 1 1 calc R U . . .
C2 C 0.5915(7) 0.4413(8) 0.6295(4) 0.039(2) Uani 1 1 d . . . . .
H2 H 0.585836 0.509351 0.642248 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6512(7) 0.1641(8) 0.3307(4) 0.043(2) Uani 1 1 d . . . . .
H14 H 0.656052 0.188002 0.296560 0.052 Uiso 1 1 calc R U . . .
C9 C 0.6236(6) -0.0293(6) 0.5060(4) 0.036(2) Uani 1 1 d . . . . .
H9 H 0.624542 -0.089080 0.485016 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6330(7) 0.0278(7) 0.3895(4) 0.039(2) Uani 1 1 d . . . . .
H12 H 0.623392 -0.043339 0.395941 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6407(7) 0.0610(8) 0.3402(4) 0.046(3) Uani 1 1 d . . . . .
H13 H 0.638868 0.012654 0.312638 0.055 Uiso 1 1 calc R U . . .
F1 F 0.6743(8) 0.3658(6) 0.2605(4) 0.121(4) Uani 1 1 d . . . . .
F3 F 0.5966(9) 0.5899(6) 0.2737(4) 0.133(4) Uani 1 1 d . . . . .
F2 F 0.6607(9) 0.4636(7) 0.3274(3) 0.129(4) Uani 1 1 d . . . . .
N5 N 0.7112(11) 0.8095(7) 0.3497(5) 0.082(4) Uani 1 1 d . . . . .
C19 C 0.7783(11) 0.7774(8) 0.3315(5) 0.057(3) Uani 1 1 d . . . . .
F5 F 0.7416(7) 0.5160(9) 0.2620(5) 0.149(4) Uani 1 1 d . . . . .
F6 F 0.5234(8) 0.4408(9) 0.2734(6) 0.169(5) Uani 1 1 d . . . . .
C18 C 0.8612(10) 0.7345(9) 0.3113(5) 0.070(4) Uani 1 1 d . . . . .
H18A H 0.836448 0.677555 0.287854 0.105 Uiso 1 1 calc R U . . .
H18B H 0.912365 0.708563 0.339881 0.105 Uiso 1 1 calc R U . . .
H18C H 0.893115 0.787120 0.291859 0.105 Uiso 1 1 calc R U . . .


_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
Ir1 Ir1 2.7389(7) 2_656 ?
Ir1 Cl1 2.4867(18) . ?
Ir1 N4 2.015(6) . ?
Ir1 N2 1.953(6) . ?
Ir1 N1 2.045(7) . ?
Ir1 N3 2.050(6) . ?
P1 F4 1.515(8) . ?
P1 F1 1.559(7) . ?
P1 F3 1.563(7) . ?
P1 F2 1.586(8) . ?
P1 F5 1.566(9) . ?
P1 F6 1.511(9) . ?
N4 C16 1.134(10) . ?
N2 C6 1.353(11) . ?
N2 C10 1.342(10) . ?
N1 C5 1.385(10) . ?
N1 C1 1.328(10) . ?
N3 C11 1.379(10) . ?
N3 C15 1.344(11) . ?
C5 C6 1.472(12) . ?
C5 C4 1.374(12) . ?
C6 C7 1.396(12) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C16 1.465(11) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(12) . ?
C8 H8 0.9500 . ?
C8 C7 1.363(13) . ?
C8 C9 1.351(13) . ?
C11 C10 1.480(12) . ?
C11 C12 1.383(11) . ?
C4 H4 0.9500 . ?
C4 C3 1.376(14) . ?
C10 C9 1.416(11) . ?
C15 H15 0.9500 . ?
C15 C14 1.400(13) . ?
C7 H7 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.372(13) . ?
C2 H2 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.372(14) . ?
C9 H9 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.368(14) . ?
C13 H13 0.9500 . ?
N5 C19 1.138(15) . ?
C19 C18 1.392(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
Cl1 Ir1 Ir1 175.34(4) . 2_656 ?
N4 Ir1 Ir1 87.62(17) . 2_656 ?
N4 Ir1 Cl1 87.91(18) . . ?
N4 Ir1 N1 98.7(3) . . ?
N4 Ir1 N3 100.1(3) . . ?
N2 Ir1 Ir1 93.31(17) . 2_656 ?
N2 Ir1 Cl1 91.15(18) . . ?
N2 Ir1 N4 179.0(2) . . ?
N2 Ir1 N1 80.8(3) . . ?
N2 Ir1 N3 80.3(3) . . ?
N1 Ir1 Ir1 92.43(19) . 2_656 ?
N1 Ir1 Cl1 86.91(19) . . ?
N1 Ir1 N3 160.6(3) . . ?
N3 Ir1 Ir1 92.94(17) . 2_656 ?
N3 Ir1 Cl1 89.18(17) . . ?
F4 P1 F1 92.0(5) . . ?
F4 P1 F3 89.5(5) . . ?
F4 P1 F2 174.7(7) . . ?
F4 P1 F5 84.1(7) . . ?
F1 P1 F3 174.7(7) . . ?
F1 P1 F2 87.8(5) . . ?
F1 P1 F5 86.3(6) . . ?
F3 P1 F2 90.2(5) . . ?
F3 P1 F5 88.7(6) . . ?
F5 P1 F2 90.6(7) . . ?
F6 P1 F4 98.8(8) . . ?
F6 P1 F1 95.5(6) . . ?
F6 P1 F3 89.3(6) . . ?
F6 P1 F2 86.5(7) . . ?
F6 P1 F5 176.5(7) . . ?
C16 N4 Ir1 175.3(7) . . ?
C6 N2 Ir1 118.3(5) . . ?
C10 N2 Ir1 118.9(6) . . ?
C10 N2 C6 122.8(7) . . ?
C5 N1 Ir1 112.6(5) . . ?
C1 N1 Ir1 129.0(6) . . ?
C1 N1 C5 118.1(7) . . ?
C11 N3 Ir1 113.0(5) . . ?
C15 N3 Ir1 128.8(6) . . ?
C15 N3 C11 118.1(7) . . ?
N1 C5 C6 115.3(7) . . ?
C4 C5 N1 120.6(8) . . ?
C4 C5 C6 124.1(8) . . ?
N2 C6 C5 112.9(7) . . ?
N2 C6 C7 118.6(8) . . ?
C7 C6 C5 128.4(8) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.7(9) . . ?
C2 C1 H1 118.1 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C9 C8 C7 121.6(8) . . ?
N4 C16 C17 176.8(10) . . ?
N3 C11 C10 114.9(7) . . ?
N3 C11 C12 121.1(8) . . ?
C12 C11 C10 124.0(8) . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.3(9) . . ?
C3 C4 H4 120.3 . . ?
N2 C10 C11 112.8(7) . . ?
N2 C10 C9 118.7(8) . . ?
C9 C10 C11 128.5(8) . . ?
N3 C15 H15 118.9 . . ?
N3 C15 C14 122.3(9) . . ?
C14 C15 H15 118.9 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.3(9) . . ?
C8 C7 H7 120.3 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.7(8) . . ?
C2 C3 H3 119.7 . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.4(9) . . ?
C3 C2 H2 121.3 . . ?
C15 C14 H14 120.7 . . ?
C13 C14 C15 118.6(9) . . ?
C13 C14 H14 120.7 . . ?
C8 C9 C10 118.9(9) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(9) . . ?
C13 C12 H12 120.1 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0(9) . . ?
C12 C13 H13 120.0 . . ?
N5 C19 C18 177.1(13) . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
Ir1 N2 C6 C5 2.4(9) . . . . ?
Ir1 N2 C6 C7 -177.9(6) . . . . ?
Ir1 N2 C10 C11 -3.7(8) . . . . ?
Ir1 N2 C10 C9 178.5(6) . . . . ?
Ir1 N1 C5 C6 1.8(9) . . . . ?
Ir1 N1 C5 C4 -177.6(7) . . . . ?
Ir1 N1 C1 C2 176.9(6) . . . . ?
Ir1 N3 C11 C10 -3.1(8) . . . . ?
Ir1 N3 C11 C12 175.1(6) . . . . ?
Ir1 N3 C15 C14 -176.0(6) . . . . ?
N2 C6 C7 C8 -1.0(12) . . . . ?
N2 C10 C9 C8 -0.3(12) . . . . ?
N1 C5 C6 N2 -2.8(10) . . . . ?
N1 C5 C6 C7 177.6(8) . . . . ?
N1 C5 C4 C3 1.4(13) . . . . ?
N1 C1 C2 C3 -2.2(13) . . . . ?
N3 C11 C10 N2 4.4(9) . . . . ?
N3 C11 C10 C9 -178.1(8) . . . . ?
N3 C11 C12 C13 2.1(12) . . . . ?
N3 C15 C14 C13 1.3(13) . . . . ?
C5 N1 C1 C2 4.2(12) . . . . ?
C5 C6 C7 C8 178.6(8) . . . . ?
C5 C4 C3 C2 0.7(14) . . . . ?
C6 N2 C10 C11 174.7(7) . . . . ?
C6 N2 C10 C9 -3.1(11) . . . . ?
C6 C5 C4 C3 -178.0(8) . . . . ?
C1 N1 C5 C6 175.7(7) . . . . ?
C1 N1 C5 C4 -3.7(12) . . . . ?
C11 N3 C15 C14 -1.4(11) . . . . ?
C11 C10 C9 C8 -177.7(8) . . . . ?
C11 C12 C13 C14 -2.1(14) . . . . ?
C4 C5 C6 N2 176.6(8) . . . . ?
C4 C5 C6 C7 -3.0(14) . . . . ?
C4 C3 C2 C1 -0.4(14) . . . . ?
C10 N2 C6 C5 -176.0(7) . . . . ?
C10 N2 C6 C7 3.7(11) . . . . ?
C10 C11 C12 C13 -179.9(8) . . . . ?
C15 N3 C11 C10 -178.5(7) . . . . ?
C15 N3 C11 C12 -0.3(11) . . . . ?
C15 C14 C13 C12 0.5(14) . . . . ?
C7 C8 C9 C10 2.9(13) . . . . ?
C9 C8 C7 C6 -2.3(13) . . . . ?
C12 C11 C10 N2 -173.8(7) . . . . ?
C12 C11 C10 C9 3.7(13) . . . . ?

_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 1.791
_oxdiff_exptl_absorpt_empirical_full_min 0.777
####################################################################### 
# 
# 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_230130_irtpyester
_database_code_depnum_ccdc_archive 'CCDC 2302206'
loop_
_audit_author_name
_audit_author_address
'SEIJI OGO'
;Kyushu University
Japan
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        IrtpyMeester
_chemical_formula_moiety         'C19 H18 Cl Ir N4 O3'
_chemical_formula_sum            'C19 H18 Cl Ir N4 O3'
_chemical_formula_weight         578.02
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ir1 C15 H11 N3 Cl1 O2'
_chemical_oxdiff_usercomment     small_Orange_ANMeOHEt2O
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'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.1369(5)
_cell_length_b                   12.5428(4)
_cell_length_c                   22.7604(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.974(3)
_cell_angle_gamma                90
_cell_volume                     3962.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7594
_cell_measurement_temperature    143
_cell_measurement_theta_max      28.9880
_cell_measurement_theta_min      2.1780
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.644
_exptl_absorpt_coefficient_mu    6.902
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2224
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16778
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.590
_diffrn_reflns_theta_min         2.189
_diffrn_ambient_temperature      143
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  74.00   0.50  100.00    --  -12.50  46.00-180.00   52
  2  ω   -101.00  76.00   0.50  100.00    --  -12.50  46.00 -90.00  354
  3  ω    -54.00 -28.00   0.50  100.00    --  -12.50  28.00  30.00   52
  4  ω     26.00  51.00   0.50  100.00    --  -12.50  28.00  30.00   50
  5  ω    -87.00   3.00   0.50  100.00    --  -12.50  46.00-180.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0483762000
_diffrn_orient_matrix_UB_12      0.0154124000
_diffrn_orient_matrix_UB_13      -0.0003070000
_diffrn_orient_matrix_UB_21      -0.0078898000
_diffrn_orient_matrix_UB_22      0.0050526000
_diffrn_orient_matrix_UB_23      -0.0315946000
_diffrn_orient_matrix_UB_31      -0.0145217000
_diffrn_orient_matrix_UB_32      -0.0541590000
_diffrn_orient_matrix_UB_33      -0.0030410000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3894
_reflns_number_total             4851
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.325
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.191
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4851
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0278P)²+4.8472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0597
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C16(H16), C11(H11), C13(H13), C17(H17), C18(H18), C12(H12), C7(H7),
 C6(H6), C8(H8), C19(H19), C5(H5)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C2(H2A,H2B,H2C)
;
_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
Ir1 Ir 0.39248(2) 0.68140(2) 0.62610(2) 0.01876(5) Uani 1 1 d . . . . .
Cl1 Cl 0.21655(7) 0.65351(8) 0.59329(4) 0.0272(2) Uani 1 1 d . . . . .
O1 O 0.5792(2) 0.7300(2) 0.69778(13) 0.0296(6) Uani 1 1 d . . . . .
O2 O 0.5821(2) 0.6482(2) 0.61023(14) 0.0351(7) Uani 1 1 d . . . . .
O3 O 0.5207(3) 0.8662(3) 0.57398(15) 0.0454(8) Uani 1 1 d . . . . .
N1 N 0.4083(2) 0.5222(2) 0.60918(15) 0.0219(7) Uani 1 1 d . . . . .
N2 N 0.3891(2) 0.6233(2) 0.70573(14) 0.0187(6) Uani 1 1 d . . . . .
N3 N 0.3714(2) 0.8189(2) 0.66964(14) 0.0208(6) Uani 1 1 d . . . . .
N4 N 0.3972(2) 0.7488(2) 0.54493(15) 0.0247(7) Uani 1 1 d . . . . .
H4 H 0.357006 0.723318 0.513764 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3815(3) 0.6922(3) 0.74996(17) 0.0201(8) Uani 1 1 d . . . . .
C16 C 0.3572(3) 0.8890(3) 0.76593(19) 0.0253(9) Uani 1 1 d . . . . .
H16 H 0.356211 0.877998 0.807106 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4043(3) 0.4748(3) 0.77099(18) 0.0261(9) Uani 1 1 d . . . . .
H11 H 0.412371 0.400390 0.778075 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3999(3) 0.5163(3) 0.71418(18) 0.0225(8) Uani 1 1 d . . . . .
C1 C 0.5355(3) 0.6950(3) 0.65091(19) 0.0248(9) Uani 1 1 d . . . . .
C13 C 0.3842(3) 0.6536(3) 0.80701(18) 0.0247(8) Uani 1 1 d . . . . .
H13 H 0.377905 0.700619 0.838772 0.030 Uiso 1 1 calc R U . . .
C17 C 0.3454(3) 0.9908(3) 0.7417(2) 0.0293(9) Uani 1 1 d . . . . .
H17 H 0.338684 1.050273 0.766435 0.035 Uiso 1 1 calc R U . . .
C18 C 0.3436(3) 1.0046(3) 0.6815(2) 0.0305(10) Uani 1 1 d . . . . .
H18 H 0.333745 1.073447 0.664087 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4091(3) 0.4593(3) 0.65860(18) 0.0233(8) Uani 1 1 d . . . . .
C12 C 0.3965(3) 0.5439(3) 0.81725(18) 0.0293(9) Uani 1 1 d . . . . .
H12 H 0.399626 0.516599 0.856501 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4252(3) 0.3042(3) 0.6013(2) 0.0348(10) Uani 1 1 d . . . . .
H7 H 0.430431 0.229018 0.598223 0.042 Uiso 1 1 calc R U . . .
C6 C 0.4245(3) 0.3681(3) 0.5513(2) 0.0353(11) Uani 1 1 d . . . . .
H6 H 0.429551 0.337187 0.513951 0.042 Uiso 1 1 calc R U . . .
C8 C 0.4183(3) 0.3500(3) 0.6553(2) 0.0283(9) Uani 1 1 d . . . . .
H8 H 0.419828 0.306903 0.689768 0.034 Uiso 1 1 calc R U . . .
C19 C 0.3563(3) 0.9174(3) 0.64671(19) 0.0267(9) Uani 1 1 d . . . . .
H19 H 0.354201 0.927587 0.605120 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4553(3) 0.8276(3) 0.5346(2) 0.0318(10) Uani 1 1 d . . . . .
C4 C 0.4375(4) 0.8748(3) 0.47234(19) 0.0388(11) Uani 1 1 d . . . . .
H4A H 0.405526 0.821912 0.443603 0.058 Uiso 1 1 calc R U . . .
H4B H 0.499167 0.895211 0.461880 0.058 Uiso 1 1 calc R U . . .
H4C H 0.396386 0.937975 0.471190 0.058 Uiso 1 1 calc R U . . .
C2 C 0.6853(3) 0.6612(4) 0.6210(2) 0.0494(13) Uani 1 1 d . . . . .
H2A H 0.712720 0.614263 0.594133 0.074 Uiso 1 1 calc R U . . .
H2B H 0.712359 0.642626 0.662643 0.074 Uiso 1 1 calc R U . . .
H2C H 0.701025 0.735448 0.613559 0.074 Uiso 1 1 calc R U . . .
C15 C 0.3705(3) 0.8031(3) 0.72957(18) 0.0218(8) Uani 1 1 d . . . . .
C5 C 0.4163(3) 0.4769(3) 0.55691(19) 0.0288(9) Uani 1 1 d . . . . .
H5 H 0.416225 0.520979 0.522939 0.035 Uiso 1 1 calc R U . . .


_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
Ir1 Cl1 2.4817(10) . ?
Ir1 N1 2.053(3) . ?
Ir1 N2 1.963(3) . ?
Ir1 N3 2.039(3) . ?
Ir1 N4 2.044(3) . ?
Ir1 C1 2.000(4) . ?
O1 C1 1.209(5) . ?
O2 C1 1.367(5) . ?
O2 C2 1.442(5) . ?
O3 C3 1.256(5) . ?
N1 C9 1.373(5) . ?
N1 C5 1.342(5) . ?
N2 C14 1.347(5) . ?
N2 C10 1.360(5) . ?
N3 C19 1.343(5) . ?
N3 C15 1.381(5) . ?
N4 H4 0.8800 . ?
N4 C3 1.334(5) . ?
C14 C13 1.379(5) . ?
C14 C15 1.465(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(6) . ?
C16 C15 1.393(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.385(5) . ?
C11 C12 1.385(6) . ?
C10 C9 1.480(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.401(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(5) . ?
C9 C8 1.381(5) . ?
C12 H12 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.390(7) . ?
C7 C8 1.375(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.378(6) . ?
C8 H8 0.9500 . ?
C19 H19 0.9500 . ?
C3 C4 1.513(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C5 H5 0.9500 . ?

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
N1 Ir1 Cl1 86.87(9) . . ?
N2 Ir1 Cl1 91.50(9) . . ?
N2 Ir1 N1 80.48(13) . . ?
N2 Ir1 N3 80.43(12) . . ?
N2 Ir1 N4 177.34(12) . . ?
N2 Ir1 C1 88.40(14) . . ?
N3 Ir1 Cl1 91.97(9) . . ?
N3 Ir1 N1 160.85(13) . . ?
N3 Ir1 N4 97.04(12) . . ?
N4 Ir1 Cl1 89.40(10) . . ?
N4 Ir1 N1 102.06(13) . . ?
C1 Ir1 Cl1 176.59(11) . . ?
C1 Ir1 N1 89.75(13) . . ?
C1 Ir1 N3 91.37(14) . . ?
C1 Ir1 N4 90.85(15) . . ?
C1 O2 C2 116.0(4) . . ?
C9 N1 Ir1 112.9(3) . . ?
C5 N1 Ir1 127.5(3) . . ?
C5 N1 C9 119.6(3) . . ?
C14 N2 Ir1 118.1(2) . . ?
C14 N2 C10 123.4(3) . . ?
C10 N2 Ir1 118.4(3) . . ?
C19 N3 Ir1 128.1(3) . . ?
C19 N3 C15 119.0(3) . . ?
C15 N3 Ir1 112.8(2) . . ?
Ir1 N4 H4 116.8 . . ?
C3 N4 Ir1 126.3(3) . . ?
C3 N4 H4 116.8 . . ?
N2 C14 C13 119.1(3) . . ?
N2 C14 C15 113.1(3) . . ?
C13 C14 C15 127.8(4) . . ?
C17 C16 H16 120.2 . . ?
C17 C16 C15 119.7(4) . . ?
C15 C16 H16 120.2 . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C12 C11 C10 118.6(4) . . ?
N2 C10 C11 119.2(4) . . ?
N2 C10 C9 112.5(3) . . ?
C11 C10 C9 128.4(3) . . ?
O1 C1 Ir1 126.8(3) . . ?
O1 C1 O2 121.5(4) . . ?
O2 C1 Ir1 111.3(3) . . ?
C14 C13 H13 120.6 . . ?
C14 C13 C12 118.8(4) . . ?
C12 C13 H13 120.6 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.3(4) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.5(4) . . ?
C19 C18 H18 120.3 . . ?
N1 C9 C10 115.7(3) . . ?
N1 C9 C8 120.8(4) . . ?
C8 C9 C10 123.5(4) . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C8 C7 C6 120.0(4) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 C7 118.9(4) . . ?
C5 C6 H6 120.6 . . ?
C9 C8 H8 120.4 . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 H8 120.4 . . ?
N3 C19 C18 122.2(4) . . ?
N3 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
O3 C3 N4 123.7(4) . . ?
O3 C3 C4 119.0(4) . . ?
N4 C3 C4 117.2(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C15 C14 115.4(3) . . ?
N3 C15 C16 120.2(3) . . ?
C16 C15 C14 124.4(4) . . ?
N1 C5 C6 121.6(4) . . ?
N1 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?

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
Ir1 N1 C9 C10 -0.8(4) . . . . ?
Ir1 N1 C9 C8 179.4(3) . . . . ?
Ir1 N1 C5 C6 -178.5(3) . . . . ?
Ir1 N2 C14 C13 -176.5(3) . . . . ?
Ir1 N2 C14 C15 3.8(4) . . . . ?
Ir1 N2 C10 C11 175.6(3) . . . . ?
Ir1 N2 C10 C9 -2.3(4) . . . . ?
Ir1 N3 C19 C18 -179.5(3) . . . . ?
Ir1 N3 C15 C14 -1.9(4) . . . . ?
Ir1 N3 C15 C16 179.8(3) . . . . ?
Ir1 N4 C3 O3 5.3(6) . . . . ?
Ir1 N4 C3 C4 -172.2(3) . . . . ?
N1 C9 C8 C7 -1.1(6) . . . . ?
N2 C14 C13 C12 1.1(5) . . . . ?
N2 C14 C15 N3 -1.1(5) . . . . ?
N2 C14 C15 C16 177.2(4) . . . . ?
N2 C10 C9 N1 2.0(5) . . . . ?
N2 C10 C9 C8 -178.3(3) . . . . ?
C14 N2 C10 C11 -0.5(5) . . . . ?
C14 N2 C10 C9 -178.5(3) . . . . ?
C14 C13 C12 C11 -1.1(6) . . . . ?
C16 C17 C18 C19 -1.8(6) . . . . ?
C11 C10 C9 N1 -175.7(4) . . . . ?
C11 C10 C9 C8 4.0(6) . . . . ?
C10 N2 C14 C13 -0.3(5) . . . . ?
C10 N2 C14 C15 180.0(3) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C10 C9 C8 C7 179.2(4) . . . . ?
C13 C14 C15 N3 179.2(4) . . . . ?
C13 C14 C15 C16 -2.5(6) . . . . ?
C17 C16 C15 N3 -0.4(6) . . . . ?
C17 C16 C15 C14 -178.6(4) . . . . ?
C17 C18 C19 N3 -0.7(6) . . . . ?
C9 N1 C5 C6 0.5(6) . . . . ?
C12 C11 C10 N2 0.6(5) . . . . ?
C12 C11 C10 C9 178.1(4) . . . . ?
C7 C6 C5 N1 -0.5(6) . . . . ?
C6 C7 C8 C9 1.1(6) . . . . ?
C8 C7 C6 C5 -0.3(6) . . . . ?
C19 N3 C15 C14 176.3(3) . . . . ?
C19 N3 C15 C16 -2.1(5) . . . . ?
C2 O2 C1 Ir1 174.9(3) . . . . ?
C2 O2 C1 O1 -11.5(6) . . . . ?
C15 N3 C19 C18 2.6(6) . . . . ?
C15 C14 C13 C12 -179.3(4) . . . . ?
C15 C16 C17 C18 2.3(6) . . . . ?
C5 N1 C9 C10 -180.0(3) . . . . ?
C5 N1 C9 C8 0.3(5) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 68 electrons were 
found in a volume of 288Å^3 in 1 void. 
This is consistent with the presence of 
0.4[CH4O] per formula unit 
which account for 72.0 electrons.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.250 0.109 0.500 71.6 16.9 '1 methanol'
2 0.250 0.391 0.000 71.6 16.9 '1 methanol'
3 0.750 0.609 1.000 71.6 16.9 '1 methanol'
4 0.750 0.891 0.500 71.6 16.9 '1 methanol'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 2.012
_oxdiff_exptl_absorpt_empirical_full_min 0.689
