# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_cxy3274
_database_code_depnum_ccdc_archive 'CCDC 2085717'
loop_
_audit_author_name
_audit_author_address
'Zengjin Dai'
;None
China
;
_audit_update_record             
;
2021-05-25 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_audit_creation_date             2021-05-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H32 Cl Ir N O P, 0.323(H2 O)'
_chemical_formula_sum            'C27 H32.65 Cl Ir N O1.32 P'
_chemical_formula_weight         650.96
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
P P 0.2955 0.4335 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   12.8894(7)
_cell_length_b                   13.1148(7)
_cell_length_c                   14.7203(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2488.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9604
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      4.52
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.144
_exptl_absorpt_correction_T_max  0.1665
_exptl_absorpt_correction_T_min  0.0376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1469 before and 0.0858 after correction.
The Ratio of minimum to maximum transmission is 0.2258.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1285
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47540
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.330
_diffrn_reflns_theta_min         4.515
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4569
_reflns_number_total             4582
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.788
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details 
;
 Flack x determined using 1970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.092
_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)+(0.0510P)²+1.1084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0682
_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,H) groups
2. Others
 Sof(O2)=Sof(H2A)=Sof(H2B)=FVAR(1)
3.a Free rotating group:
 O2(H2A,H2B)
3.b Ternary CH refined with riding coordinates:
 C2(H2)
3.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C1(H1A,H1B), C4(H4A,H4B)
3.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C13(H13), C17(H17), C8(H8), C7(H7), C11(H11), C16(H16),
 C9(H9), C10(H10)
3.e Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23(H23A,H23B,
 H23C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.26790(2) 0.68655(2) 0.17442(2) 0.02338(10) Uani 1 1 d . . . . .
Cl1 Cl 0.36990(12) 0.62773(11) 0.04623(9) 0.0302(3) Uani 1 1 d . . . . .
P1 P 0.12488(12) 0.62055(11) 0.10505(10) 0.0251(3) Uani 1 1 d . . . . .
O1 O 0.3883(4) 0.8977(3) 0.0961(3) 0.0331(10) Uani 1 1 d . . . . .
N1 N 0.2344(4) 0.8068(4) 0.0885(3) 0.0271(10) Uani 1 1 d . . . . .
C3 C 0.3006(5) 0.8816(5) 0.0655(4) 0.0277(12) Uani 1 1 d . . . . .
C26 C 0.3287(6) 0.8906(5) 0.3031(4) 0.0329(14) Uani 1 1 d . . . . .
H26A H 0.365538 0.918755 0.250496 0.049 Uiso 1 1 calc R U . . .
H26B H 0.367074 0.906889 0.358688 0.049 Uiso 1 1 calc R U . . .
H26C H 0.259075 0.920358 0.306415 0.049 Uiso 1 1 calc R U . . .
C15 C 0.1326(6) 0.2850(5) 0.0144(4) 0.0378(15) Uani 1 1 d . . . . .
H15 H 0.131928 0.214813 -0.001437 0.045 Uiso 1 1 calc R U . . .
C14 C 0.0540(6) 0.3475(5) -0.0144(4) 0.0352(14) Uani 1 1 d . . . . .
H14 H 0.000420 0.320443 -0.051541 0.042 Uiso 1 1 calc R U . . .
C13 C 0.0514(5) 0.4508(5) 0.0102(4) 0.0286(12) Uani 1 1 d . . . . .
H13 H -0.003589 0.493544 -0.009660 0.034 Uiso 1 1 calc R U . . .
C18 C 0.4021(5) 0.7123(5) 0.2662(4) 0.0287(13) Uani 1 1 d . . . . .
C5 C 0.1622(5) 0.8825(5) -0.0443(4) 0.0326(13) Uani 1 1 d . . . . .
H5A H 0.184191 0.843346 -0.098468 0.039 Uiso 1 1 calc R U . . .
H5B H 0.101369 0.924866 -0.060264 0.039 Uiso 1 1 calc R U . . .
C24 C 0.2008(6) 0.5199(5) 0.3406(4) 0.0360(14) Uani 1 1 d . . . . .
H24A H 0.126882 0.537130 0.342116 0.054 Uiso 1 1 calc R U . . .
H24B H 0.224105 0.501415 0.401777 0.054 Uiso 1 1 calc R U . . .
H24C H 0.211859 0.462194 0.299390 0.054 Uiso 1 1 calc R U . . .
C17 C 0.2130(5) 0.4269(5) 0.0920(4) 0.0319(13) Uani 1 1 d . . . . .
H17 H 0.267682 0.454133 0.127791 0.038 Uiso 1 1 calc R U . . .
C8 C -0.1111(6) 0.5329(5) 0.2752(4) 0.0355(14) Uani 1 1 d . . . . .
H8 H -0.127103 0.474948 0.311237 0.043 Uiso 1 1 calc R U . . .
C6 C 0.0033(5) 0.6189(5) 0.1682(4) 0.0290(12) Uani 1 1 d . . . . .
C7 C -0.0223(5) 0.5333(5) 0.2206(4) 0.0321(13) Uani 1 1 d . . . . .
H7 H 0.021218 0.474820 0.219108 0.039 Uiso 1 1 calc R U . . .
C20 C 0.2296(5) 0.7161(5) 0.3152(4) 0.0282(12) Uani 1 1 d . . . . .
C19 C 0.3202(5) 0.7768(5) 0.2933(4) 0.0272(13) Uani 1 1 d . . . . .
C25 C 0.1306(6) 0.7539(5) 0.3573(5) 0.0353(14) Uani 1 1 d . . . . .
H25A H 0.117557 0.824127 0.337705 0.053 Uiso 1 1 calc R U . . .
H25B H 0.136749 0.751822 0.423653 0.053 Uiso 1 1 calc R U . . .
H25C H 0.072832 0.710294 0.338107 0.053 Uiso 1 1 calc R U . . .
C22 C 0.3640(6) 0.6084(5) 0.2758(4) 0.0294(13) Uani 1 1 d . . . . .
C1 C 0.1041(5) 0.7038(4) 0.0069(4) 0.0287(12) Uani 1 1 d . . . . .
H1A H 0.146029 0.680192 -0.045355 0.034 Uiso 1 1 calc R U . . .
H1B H 0.030048 0.703383 -0.010908 0.034 Uiso 1 1 calc R U . . .
C2 C 0.1373(5) 0.8110(5) 0.0354(4) 0.0283(11) Uani 1 1 d . . . . .
H2 H 0.081455 0.842221 0.073436 0.034 Uiso 1 1 calc R U . . .
C23 C 0.4295(6) 0.5141(5) 0.2607(4) 0.0357(14) Uani 1 1 d . . . . .
H23A H 0.384900 0.453568 0.261272 0.054 Uiso 1 1 calc R U . . .
H23B H 0.481282 0.508556 0.309197 0.054 Uiso 1 1 calc R U . . .
H23C H 0.464713 0.519069 0.201861 0.054 Uiso 1 1 calc R U . . .
C11 C -0.0631(5) 0.7027(5) 0.1702(4) 0.0328(13) Uani 1 1 d . . . . .
H11 H -0.047298 0.761126 0.134651 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2135(6) 0.3239(5) 0.0667(4) 0.0353(14) Uani 1 1 d . . . . .
H16 H 0.268886 0.280792 0.085057 0.042 Uiso 1 1 calc R U . . .
C12 C 0.1306(5) 0.4894(5) 0.0639(4) 0.0279(12) Uani 1 1 d . . . . .
C9 C -0.1757(6) 0.6172(5) 0.2764(5) 0.0383(15) Uani 1 1 d . . . . .
H9 H -0.235903 0.617108 0.313585 0.046 Uiso 1 1 calc R U . . .
C27 C 0.5092(5) 0.7432(5) 0.2398(4) 0.0329(13) Uani 1 1 d . . . . .
H27A H 0.544233 0.685730 0.210401 0.049 Uiso 1 1 calc R U . . .
H27B H 0.547949 0.763468 0.294137 0.049 Uiso 1 1 calc R U . . .
H27C H 0.505696 0.800817 0.197477 0.049 Uiso 1 1 calc R U . . .
C4 C 0.2507(5) 0.9480(5) -0.0083(4) 0.0311(13) Uani 1 1 d . . . . .
H4A H 0.224105 1.012593 0.017628 0.037 Uiso 1 1 calc R U . . .
H4B H 0.301035 0.963958 -0.057033 0.037 Uiso 1 1 calc R U . . .
C10 C -0.1528(6) 0.7019(5) 0.2237(5) 0.0366(14) Uani 1 1 d . . . . .
H10 H -0.197905 0.759245 0.223893 0.044 Uiso 1 1 calc R U . . .
C21 C 0.2616(6) 0.6102(5) 0.3075(4) 0.0298(12) Uani 1 1 d . . . . .
O2 O 0.4765(17) 0.4068(14) 0.0331(14) 0.058(7) Uani 0.32(2) 1 d G . P . .
H2A H 0.471859 0.346972 0.007876 0.087 Uiso 0.32(2) 1 d G U P . .
H2B H 0.538323 0.431379 0.024364 0.087 Uiso 0.32(2) 1 d G U P . .


_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 2.4258(14) . ?
Ir1 P1 2.2781(15) . ?
Ir1 N1 2.067(5) . ?
Ir1 C18 2.221(6) . ?
Ir1 C20 2.165(6) . ?
Ir1 C19 2.217(6) . ?
Ir1 C22 2.194(6) . ?
Ir1 C21 2.202(6) . ?
P1 C6 1.822(6) . ?
P1 C1 1.830(6) . ?
P1 C12 1.825(6) . ?
O1 C3 1.236(8) . ?
N1 C3 1.343(8) . ?
N1 C2 1.477(7) . ?
C3 C4 1.533(8) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C26 C19 1.504(9) . ?
C15 H15 0.9500 . ?
C15 C14 1.370(11) . ?
C15 C16 1.393(11) . ?
C14 H14 0.9500 . ?
C14 C13 1.402(9) . ?
C13 H13 0.9500 . ?
C13 C12 1.387(9) . ?
C18 C19 1.410(9) . ?
C18 C22 1.456(9) . ?
C18 C27 1.490(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C2 1.535(8) . ?
C5 C4 1.523(9) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C21 1.501(9) . ?
C17 H17 0.9500 . ?
C17 C16 1.401(9) . ?
C17 C12 1.403(9) . ?
C8 H8 0.9500 . ?
C8 C7 1.398(10) . ?
C8 C9 1.384(10) . ?
C6 C7 1.403(9) . ?
C6 C11 1.393(9) . ?
C7 H7 0.9500 . ?
C20 C19 1.450(9) . ?
C20 C25 1.503(9) . ?
C20 C21 1.454(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C22 C23 1.514(9) . ?
C22 C21 1.400(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.529(8) . ?
C2 H2 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C10 1.399(10) . ?
C16 H16 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.387(10) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C10 H10 0.9500 . ?
O2 H2A 0.8702 . ?
O2 H2B 0.8698 . ?

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
P1 Ir1 Cl1 88.23(5) . . ?
N1 Ir1 Cl1 83.11(14) . . ?
N1 Ir1 P1 81.19(15) . . ?
N1 Ir1 C18 114.7(2) . . ?
N1 Ir1 C20 113.6(2) . . ?
N1 Ir1 C19 98.0(2) . . ?
N1 Ir1 C22 152.9(2) . . ?
N1 Ir1 C21 152.1(2) . . ?
C18 Ir1 Cl1 95.71(17) . . ?
C18 Ir1 P1 163.91(16) . . ?
C20 Ir1 Cl1 157.69(17) . . ?
C20 Ir1 P1 108.20(17) . . ?
C20 Ir1 C18 64.4(2) . . ?
C20 Ir1 C19 38.6(2) . . ?
C20 Ir1 C22 64.0(2) . . ?
C20 Ir1 C21 38.9(2) . . ?
C19 Ir1 Cl1 128.21(18) . . ?
C19 Ir1 P1 143.38(18) . . ?
C19 Ir1 C18 37.0(2) . . ?
C22 Ir1 Cl1 94.26(17) . . ?
C22 Ir1 P1 125.76(18) . . ?
C22 Ir1 C18 38.5(2) . . ?
C22 Ir1 C19 62.7(2) . . ?
C22 Ir1 C21 37.2(3) . . ?
C21 Ir1 Cl1 124.58(18) . . ?
C21 Ir1 P1 101.33(18) . . ?
C21 Ir1 C18 63.7(2) . . ?
C21 Ir1 C19 63.4(2) . . ?
C6 P1 Ir1 118.2(2) . . ?
C6 P1 C1 106.5(3) . . ?
C6 P1 C12 101.1(3) . . ?
C1 P1 Ir1 104.2(2) . . ?
C12 P1 Ir1 118.3(2) . . ?
C12 P1 C1 107.8(3) . . ?
C3 N1 Ir1 125.4(4) . . ?
C3 N1 C2 112.2(5) . . ?
C2 N1 Ir1 121.9(4) . . ?
O1 C3 N1 127.9(6) . . ?
O1 C3 C4 123.0(6) . . ?
N1 C3 C4 109.1(5) . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C19 C26 H26A 109.5 . . ?
C19 C26 H26B 109.5 . . ?
C19 C26 H26C 109.5 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(6) . . ?
C16 C15 H15 119.8 . . ?
C15 C14 H14 119.5 . . ?
C15 C14 C13 121.0(7) . . ?
C13 C14 H14 119.5 . . ?
C14 C13 H13 120.6 . . ?
C12 C13 C14 118.8(6) . . ?
C12 C13 H13 120.6 . . ?
C19 C18 Ir1 71.3(4) . . ?
C19 C18 C22 106.4(6) . . ?
C19 C18 C27 127.2(6) . . ?
C22 C18 Ir1 69.7(4) . . ?
C22 C18 C27 126.3(6) . . ?
C27 C18 Ir1 127.2(4) . . ?
H5A C5 H5B 109.0 . . ?
C2 C5 H5A 111.0 . . ?
C2 C5 H5B 111.0 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
C4 C5 C2 103.6(5) . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C12 119.2(6) . . ?
C12 C17 H17 120.4 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.8(6) . . ?
C7 C6 P1 119.5(5) . . ?
C11 C6 P1 122.0(5) . . ?
C11 C6 C7 118.4(6) . . ?
C8 C7 C6 120.7(6) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C19 C20 Ir1 72.6(3) . . ?
C19 C20 C25 126.5(6) . . ?
C19 C20 C21 106.1(6) . . ?
C25 C20 Ir1 130.4(4) . . ?
C21 C20 Ir1 71.9(3) . . ?
C21 C20 C25 126.0(6) . . ?
C26 C19 Ir1 128.9(4) . . ?
C18 C19 Ir1 71.6(3) . . ?
C18 C19 C26 124.6(6) . . ?
C18 C19 C20 109.7(5) . . ?
C20 C19 Ir1 68.7(3) . . ?
C20 C19 C26 125.6(6) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C22 Ir1 71.8(4) . . ?
C18 C22 C23 124.3(6) . . ?
C23 C22 Ir1 126.7(4) . . ?
C21 C22 Ir1 71.7(4) . . ?
C21 C22 C18 109.5(6) . . ?
C21 C22 C23 126.0(6) . . ?
P1 C1 H1A 110.3 . . ?
P1 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
C2 C1 P1 107.0(4) . . ?
C2 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
N1 C2 C5 104.5(5) . . ?
N1 C2 C1 110.4(5) . . ?
N1 C2 H2 109.2 . . ?
C5 C2 H2 109.2 . . ?
C1 C2 C5 114.3(5) . . ?
C1 C2 H2 109.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C6 C11 H11 119.5 . . ?
C6 C11 C10 120.9(6) . . ?
C10 C11 H11 119.5 . . ?
C15 C16 C17 119.7(6) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C13 C12 P1 120.2(5) . . ?
C13 C12 C17 120.8(6) . . ?
C17 C12 P1 118.9(5) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(7) . . ?
C10 C9 H9 119.8 . . ?
C18 C27 H27A 109.5 . . ?
C18 C27 H27B 109.5 . . ?
C18 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C3 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C5 C4 C3 103.9(5) . . ?
C5 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.7(6) . . ?
C9 C10 H10 120.1 . . ?
C24 C21 Ir1 131.8(4) . . ?
C20 C21 Ir1 69.2(3) . . ?
C20 C21 C24 125.5(6) . . ?
C22 C21 Ir1 71.1(3) . . ?
C22 C21 C24 125.9(6) . . ?
C22 C21 C20 108.1(6) . . ?
H2A O2 H2B 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 P1 C6 C7 -91.1(5) . . . . ?
Ir1 P1 C6 C11 85.2(5) . . . . ?
Ir1 P1 C1 C2 -33.8(4) . . . . ?
Ir1 P1 C12 C13 -170.9(4) . . . . ?
Ir1 P1 C12 C17 12.9(6) . . . . ?
Ir1 N1 C3 O1 -6.8(9) . . . . ?
Ir1 N1 C3 C4 173.0(4) . . . . ?
Ir1 N1 C2 C5 -157.2(4) . . . . ?
Ir1 N1 C2 C1 -33.9(6) . . . . ?
Ir1 C18 C19 C26 -125.1(6) . . . . ?
Ir1 C18 C19 C20 58.3(4) . . . . ?
Ir1 C18 C22 C23 122.4(6) . . . . ?
Ir1 C18 C22 C21 -62.2(4) . . . . ?
Ir1 C20 C19 C26 123.4(6) . . . . ?
Ir1 C20 C19 C18 -60.1(4) . . . . ?
Ir1 C20 C21 C24 -127.2(6) . . . . ?
Ir1 C20 C21 C22 60.8(4) . . . . ?
Ir1 C22 C21 C24 128.4(6) . . . . ?
Ir1 C22 C21 C20 -59.6(4) . . . . ?
P1 C6 C7 C8 175.1(5) . . . . ?
P1 C6 C11 C10 -175.9(5) . . . . ?
P1 C1 C2 N1 42.1(6) . . . . ?
P1 C1 C2 C5 159.5(4) . . . . ?
O1 C3 C4 C5 162.9(6) . . . . ?
N1 C3 C4 C5 -16.9(7) . . . . ?
C3 N1 C2 C5 15.1(7) . . . . ?
C3 N1 C2 C1 138.4(5) . . . . ?
C15 C14 C13 C12 0.5(9) . . . . ?
C14 C15 C16 C17 1.7(10) . . . . ?
C14 C13 C12 P1 -175.0(5) . . . . ?
C14 C13 C12 C17 1.1(9) . . . . ?
C18 C22 C21 Ir1 62.2(4) . . . . ?
C18 C22 C21 C24 -169.4(6) . . . . ?
C18 C22 C21 C20 2.6(6) . . . . ?
C8 C9 C10 C11 -1.1(11) . . . . ?
C6 P1 C1 C2 91.8(4) . . . . ?
C6 P1 C12 C13 58.4(5) . . . . ?
C6 P1 C12 C17 -117.8(5) . . . . ?
C6 C11 C10 C9 0.7(10) . . . . ?
C7 C8 C9 C10 0.2(10) . . . . ?
C7 C6 C11 C10 0.5(9) . . . . ?
C19 C18 C22 Ir1 62.4(4) . . . . ?
C19 C18 C22 C23 -175.2(6) . . . . ?
C19 C18 C22 C21 0.2(7) . . . . ?
C19 C20 C21 Ir1 -65.1(4) . . . . ?
C19 C20 C21 C24 167.7(6) . . . . ?
C19 C20 C21 C22 -4.3(6) . . . . ?
C25 C20 C19 Ir1 -127.8(6) . . . . ?
C25 C20 C19 C26 -4.5(10) . . . . ?
C25 C20 C19 C18 172.1(6) . . . . ?
C25 C20 C21 Ir1 127.3(6) . . . . ?
C25 C20 C21 C24 0.1(10) . . . . ?
C25 C20 C21 C22 -172.0(6) . . . . ?
C22 C18 C19 Ir1 -61.3(4) . . . . ?
C22 C18 C19 C26 173.6(6) . . . . ?
C22 C18 C19 C20 -3.0(7) . . . . ?
C1 P1 C6 C7 152.2(5) . . . . ?
C1 P1 C6 C11 -31.4(6) . . . . ?
C1 P1 C12 C13 -53.1(6) . . . . ?
C1 P1 C12 C17 130.7(5) . . . . ?
C2 N1 C3 O1 -178.7(6) . . . . ?
C2 N1 C3 C4 1.1(7) . . . . ?
C2 C5 C4 C3 24.8(6) . . . . ?
C23 C22 C21 Ir1 -122.5(6) . . . . ?
C23 C22 C21 C24 5.9(10) . . . . ?
C23 C22 C21 C20 177.9(6) . . . . ?
C11 C6 C7 C8 -1.4(9) . . . . ?
C16 C15 C14 C13 -1.9(10) . . . . ?
C16 C17 C12 P1 174.9(5) . . . . ?
C16 C17 C12 C13 -1.3(9) . . . . ?
C12 P1 C6 C7 39.7(5) . . . . ?
C12 P1 C6 C11 -144.0(5) . . . . ?
C12 P1 C1 C2 -160.3(4) . . . . ?
C12 C17 C16 C15 -0.2(9) . . . . ?
C9 C8 C7 C6 1.1(10) . . . . ?
C27 C18 C19 Ir1 123.0(6) . . . . ?
C27 C18 C19 C26 -2.1(10) . . . . ?
C27 C18 C19 C20 -178.7(5) . . . . ?
C27 C18 C22 Ir1 -121.9(6) . . . . ?
C27 C18 C22 C23 0.5(9) . . . . ?
C27 C18 C22 C21 176.0(6) . . . . ?
C4 C5 C2 N1 -24.5(6) . . . . ?
C4 C5 C2 C1 -145.2(5) . . . . ?
C21 C20 C19 Ir1 64.6(4) . . . . ?
C21 C20 C19 C26 -172.0(6) . . . . ?
C21 C20 C19 C18 4.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
