# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1828919'
_audit_update_record             
;
2018-03-12 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;
_audit_creation_date             2018-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 Cl Ir N3 O, F6 P'
_chemical_formula_sum            'C20 H26 Cl F6 Ir N3 O P'
_chemical_formula_weight         697.06
_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 0.0033 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'
O O 0.0106 0.0060 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   13.5409(7)
_cell_length_b                   12.9814(8)
_cell_length_c                   13.6168(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2393.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.821
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30879
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_min         2.992
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2001
_reflns_number_total             2380
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.830
_refine_diff_density_min         -2.260
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.035
_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)+(0.0543P)²+6.8434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1115
_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. Restrained distances
 C5-C6 \\sim C6-N2
 with sigma of 0.02
3. Rigid bond restraints
 C10, C9, N2, C7, C8, N3, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F2, F3, F4, F1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C10 \\sim C9 \\sim N2 \\sim C7 \\sim C8 \\sim N3 \\sim C6: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
F3 \\sim F4 \\sim F1 \\sim F2: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F1) \\sim
Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Others
 Fixed Sof: Cl1(0.5) C6(0.5) H6A(0.5) H6B(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
 C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) O1(0.5) H1(0.5) C2(0.5) H2(0.5) C3(0.5)
 H3(0.5) C4(0.5) H4(0.5) C5(0.5) N1(0.5) C1(0.5) C9(0.5) N2(0.5) C7(0.5)
 H7(0.5) C8(0.5) H8(0.5) N3(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8)
6.c Fitted pentagon refined as free rotating group:
 C9(N2,C7,C8,N3)
6.d Fitted hexagon refined as free rotating group:
 C2(C3,C4,C5,N1,C1)
6.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C14(H14A,H14B,
 H14C)
6.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.10971(2) 0.2500 0.32693(2) 0.05750(18) Uani 1 2 d S T P A .
P1 P 0.5229(3) 0.2500 0.6851(2) 0.0839(9) Uani 1 2 d S T P . .
Cl1 Cl 0.2302(2) 0.2136(3) 0.1948(2) 0.0693(12) Uani 0.5 1 d . . . A .
C11 C -0.0125(4) 0.1946(6) 0.2335(5) 0.0647(18) Uani 1 1 d . . . . .
C13 C -0.0335(6) 0.2500 0.3936(7) 0.057(2) Uani 1 2 d S T P A .
C12 C -0.0284(4) 0.1601(6) 0.3310(5) 0.0582(16) Uani 1 1 d . . . . .
C6 C 0.2052(9) 0.2643(11) 0.5477(8) 0.057(3) Uani 0.5 1 d D U . A -1
H6A H 0.2403 0.2674 0.6097 0.068 Uiso 0.5 1 calc R . . A -1
H6B H 0.1350 0.2632 0.5619 0.068 Uiso 0.5 1 calc R . . A -1
F1 F 0.6224(12) 0.2500 0.6337(19) 0.265(11) Uani 1 2 d S TU P . .
C16 C -0.0641(9) 0.2500 0.5008(8) 0.098(4) Uani 1 2 d S T P . .
H16A H -0.0656 0.1805 0.5248 0.147 Uiso 0.5 1 calc GR . . B -1
H16B H -0.1286 0.2801 0.5070 0.147 Uiso 0.5 1 calc GR . . B -1
H16C H -0.0176 0.2894 0.5384 0.147 Uiso 0.5 1 calc GR . . B -1
C10 C 0.2033(14) -0.0266(13) 0.3056(13) 0.081(4) Uani 0.5 1 d . U . A -1
H10A H 0.1764 -0.0919 0.3250 0.122 Uiso 0.5 1 calc GR . . A -1
H10B H 0.2645 -0.0372 0.2714 0.122 Uiso 0.5 1 calc GR . . A -1
H10C H 0.1575 0.0080 0.2631 0.122 Uiso 0.5 1 calc GR . . A -1
C15 C -0.0401(8) 0.0516(7) 0.3646(10) 0.111(3) Uani 1 1 d . . . . .
H15A H -0.0041 0.0067 0.3216 0.167 Uiso 1 1 calc GR . . . .
H15B H -0.1087 0.0333 0.3638 0.167 Uiso 1 1 calc GR . . . .
H15C H -0.0149 0.0450 0.4302 0.167 Uiso 1 1 calc GR . . . .
C14 C -0.0057(7) 0.1275(10) 0.1436(7) 0.115(4) Uani 1 1 d . . . . .
H14A H -0.0671 0.1299 0.1085 0.173 Uiso 1 1 calc GR . . . .
H14B H 0.0079 0.0579 0.1630 0.173 Uiso 1 1 calc GR . . . .
H14C H 0.0465 0.1520 0.1020 0.173 Uiso 1 1 calc GR . . . .
F2 F 0.4939(11) 0.3339(11) 0.6184(8) 0.297(8) Uani 1 1 d . U . . .
O1 O 0.2049(9) 0.4367(10) 0.2381(8) 0.084(3) Uani 0.5 1 d . . . A -1
H1 H 0.1943 0.3773 0.2205 0.127 Uiso 0.5 1 calc GR . . A -1
F4 F 0.5569(11) 0.1700(7) 0.7606(8) 0.233(5) Uani 1 1 d . U . . .
F3 F 0.4236(13) 0.2500 0.7348(16) 0.289(12) Uani 1 2 d S TU P . .
C2 C 0.2669(10) 0.5256(7) 0.3725(10) 0.083(5) Uani 0.5 1 d . . . A -1
H2 H 0.2799 0.5826 0.3331 0.099 Uiso 0.5 1 calc R . . A -1
C3 C 0.2902(12) 0.5282(9) 0.4719(10) 0.091(7) Uani 0.5 1 d G . . A -1
H3 H 0.3187 0.5868 0.4990 0.109 Uiso 0.5 1 calc R . . A -1
C4 C 0.2708(13) 0.4431(12) 0.5308(7) 0.054(5) Uani 0.5 1 d G . . A -1
H4 H 0.2864 0.4448 0.5973 0.065 Uiso 0.5 1 calc R . . A -1
C5 C 0.2282(13) 0.3554(10) 0.4903(9) 0.036(3) Uani 0.5 1 d DG . . A -1
N1 N 0.2050(12) 0.3529(7) 0.3909(10) 0.058(5) Uani 0.5 1 d G . . A -1
C1 C 0.2243(9) 0.4380(8) 0.3320(7) 0.066(4) Uani 0.5 1 d G . . A -1
C9 C 0.1904(14) 0.1380(9) 0.4064(12) 0.052(4) Uani 0.5 1 d . U . A -1
N2 N 0.2319(17) 0.1711(9) 0.4968(12) 0.064(4) Uani 0.5 1 d DG U . A -1
C7 C 0.2876(14) 0.0882(12) 0.5363(9) 0.058(4) Uani 0.5 1 d G U . A -1
H7 H 0.3225 0.0890 0.5951 0.070 Uiso 0.5 1 calc R . . A -1
C8 C 0.2804(10) 0.0038(9) 0.4704(11) 0.068(4) Uani 0.5 1 d G U . A -1
H8 H 0.3099 -0.0604 0.4783 0.082 Uiso 0.5 1 calc R . . A -1
N3 N 0.2204(7) 0.0346(8) 0.3901(7) 0.061(3) Uani 0.5 1 d G U . A -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 Cl1 2.474(3) 7_565 ?
Ir1 Cl1 2.474(3) . ?
Ir1 C11 2.208(6) 7_565 ?
Ir1 C11 2.208(6) . ?
Ir1 C13 2.141(8) . ?
Ir1 C12 2.205(6) 7_565 ?
Ir1 C12 2.205(6) . ?
Ir1 N1 2.050(10) . ?
Ir1 C9 2.116(10) . ?
P1 F1 1.518(14) . ?
P1 F2 1.471(9) . ?
P1 F2 1.471(9) 7_565 ?
P1 F4 1.532(9) . ?
P1 F4 1.532(9) 7_565 ?
P1 F3 1.505(15) . ?
Cl1 Cl1 0.944(8) 7_565 ?
C11 C11 1.438(16) 7_565 ?
C11 C12 1.419(9) . ?
C11 C14 1.505(10) . ?
C13 C12 1.447(9) 7_565 ?
C13 C12 1.447(9) . ?
C13 C16 1.517(14) . ?
C12 C15 1.489(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.451(11) . ?
C6 N2 1.440(13) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 N3 1.417(18) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1 H1 0.8200 . ?
O1 C1 1.306(13) . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C2 C1 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 N1 1.3900 . ?
N1 C1 1.3900 . ?
C9 N2 1.4200 . ?
C9 N3 1.4200 . ?
N2 C7 1.4200 . ?
C7 H7 0.9300 . ?
C7 C8 1.4200 . ?
C8 H8 0.9300 . ?
C8 N3 1.4200 . ?

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 Cl1 21.99(19) . 7_565 ?
C11 Ir1 Cl1 97.9(2) . 7_565 ?
C11 Ir1 Cl1 97.9(2) 7_565 . ?
C11 Ir1 Cl1 90.75(19) . . ?
C11 Ir1 Cl1 90.75(19) 7_565 7_565 ?
C11 Ir1 C11 38.0(4) 7_565 . ?
C13 Ir1 Cl1 154.9(2) . 7_565 ?
C13 Ir1 Cl1 154.9(2) . . ?
C13 Ir1 C11 64.3(3) . 7_565 ?
C13 Ir1 C11 64.3(3) . . ?
C13 Ir1 C12 38.9(2) . 7_565 ?
C13 Ir1 C12 38.9(2) . . ?
C12 Ir1 Cl1 118.5(2) . . ?
C12 Ir1 Cl1 132.73(19) . 7_565 ?
C12 Ir1 Cl1 132.73(19) 7_565 . ?
C12 Ir1 Cl1 118.5(2) 7_565 7_565 ?
C12 Ir1 C11 63.3(2) . 7_565 ?
C12 Ir1 C11 37.5(2) 7_565 7_565 ?
C12 Ir1 C11 37.5(2) . . ?
C12 Ir1 C11 63.3(2) 7_565 . ?
C12 Ir1 C12 63.9(4) . 7_565 ?
N1 Ir1 Cl1 91.0(5) . . ?
N1 Ir1 Cl1 76.7(4) . 7_565 ?
N1 Ir1 C11 120.3(4) . 7_565 ?
N1 Ir1 C11 158.2(4) . . ?
N1 Ir1 C13 112.9(5) . . ?
N1 Ir1 C12 100.3(5) . 7_565 ?
N1 Ir1 C12 150.2(5) . . ?
N1 Ir1 C9 84.6(3) . . ?
C9 Ir1 Cl1 99.3(6) . 7_565 ?
C9 Ir1 Cl1 84.3(5) . . ?
C9 Ir1 C11 117.3(5) . . ?
C9 Ir1 C11 154.9(5) . 7_565 ?
C9 Ir1 C13 104.5(6) . . ?
C9 Ir1 C12 142.0(6) . 7_565 ?
C9 Ir1 C12 93.5(6) . . ?
F1 P1 F4 92.4(9) . 7_565 ?
F1 P1 F4 92.4(9) . . ?
F2 P1 F1 87.2(9) 7_565 . ?
F2 P1 F1 87.2(9) . . ?
F2 P1 F2 95.5(13) 7_565 . ?
F2 P1 F4 174.9(8) 7_565 7_565 ?
F2 P1 F4 174.9(8) . . ?
F2 P1 F4 89.6(8) . 7_565 ?
F2 P1 F4 89.6(8) 7_565 . ?
F2 P1 F3 92.3(8) . . ?
F2 P1 F3 92.3(8) 7_565 . ?
F4 P1 F4 85.3(9) 7_565 . ?
F3 P1 F1 179.3(14) . . ?
F3 P1 F4 88.1(8) . 7_565 ?
F3 P1 F4 88.1(8) . . ?
Cl1 Cl1 Ir1 79.00(9) 7_565 . ?
C11 C11 Ir1 71.0(2) 7_565 . ?
C11 C11 C14 125.4(6) 7_565 . ?
C12 C11 Ir1 71.1(4) . . ?
C12 C11 C11 108.4(4) . 7_565 ?
C12 C11 C14 126.0(8) . . ?
C14 C11 Ir1 127.7(5) . . ?
C12 C13 Ir1 73.0(4) 7_565 . ?
C12 C13 Ir1 73.0(4) . . ?
C12 C13 C12 107.5(8) 7_565 . ?
C12 C13 C16 125.4(4) 7_565 . ?
C12 C13 C16 125.4(4) . . ?
C16 C13 Ir1 131.0(7) . . ?
C11 C12 Ir1 71.4(4) . . ?
C11 C12 C13 107.7(6) . . ?
C11 C12 C15 127.1(8) . . ?
C13 C12 Ir1 68.2(4) . . ?
C13 C12 C15 125.2(8) . . ?
C15 C12 Ir1 126.7(6) . . ?
H6A C6 H6B 107.9 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
N2 C6 C5 111.8(9) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 122.8(10) . . ?
N1 C5 C6 117.2(10) . . ?
N1 C5 C4 120.0 . . ?
C5 N1 Ir1 124.9(7) . . ?
C1 N1 Ir1 113.0(7) . . ?
C1 N1 C5 120.0 . . ?
O1 C1 C2 118.8(9) . . ?
O1 C1 N1 121.1(9) . . ?
N1 C1 C2 120.0 . . ?
N2 C9 Ir1 116.1(9) . . ?
N2 C9 N3 108.0 . . ?
N3 C9 Ir1 135.8(9) . . ?
C9 N2 C6 124.9(14) . . ?
C9 N2 C7 108.0 . . ?
C7 N2 C6 126.0(13) . . ?
N2 C7 H7 126.0 . . ?
C8 C7 N2 108.0 . . ?
C8 C7 H7 126.0 . . ?
C7 C8 H8 126.0 . . ?
C7 C8 N3 108.0 . . ?
N3 C8 H8 126.0 . . ?
C10 N3 C9 127.6(11) . . ?
C10 N3 C8 124.1(11) . . ?
C8 N3 C9 108.0 . . ?

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 C11 C12 C13 58.7(5) . . . . ?
Ir1 C11 C12 C15 -122.4(8) . . . . ?
Ir1 C13 C12 C11 -60.7(5) . . . . ?
Ir1 C13 C12 C15 120.4(7) . . . . ?
Ir1 N1 C1 O1 -17.1(13) . . . . ?
Ir1 N1 C1 C2 164.3(11) . . . . ?
Ir1 C9 N2 C6 14.8(14) . . . . ?
Ir1 C9 N2 C7 -176.7(15) . . . . ?
Ir1 C9 N3 C10 1(2) . . . . ?
Ir1 C9 N3 C8 175.7(19) . . . . ?
C11 C11 C12 Ir1 -61.55(18) 7_565 . . . ?
C11 C11 C12 C13 -2.8(6) 7_565 . . . ?
C11 C11 C12 C15 176.0(7) 7_565 . . . ?
C12 C13 C12 Ir1 65.3(6) 7_565 . . . ?
C12 C13 C12 C11 4.5(9) 7_565 . . . ?
C12 C13 C12 C15 -174.3(6) 7_565 . . . ?
C6 C5 N1 Ir1 17.1(12) . . . . ?
C6 C5 N1 C1 179.4(15) . . . . ?
C6 N2 C7 C8 168(2) . . . . ?
C16 C13 C12 Ir1 -128.6(10) . . . . ?
C16 C13 C12 C11 170.7(9) . . . . ?
C16 C13 C12 C15 -8.2(13) . . . . ?
C14 C11 C12 Ir1 123.4(7) . . . . ?
C14 C11 C12 C13 -177.9(7) . . . . ?
C14 C11 C12 C15 0.9(11) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C2 C1 O1 -178.7(13) . . . . ?
C3 C2 C1 N1 0.0 . . . . ?
C3 C4 C5 C6 -179.4(16) . . . . ?
C3 C4 C5 N1 0.0 . . . . ?
C4 C5 N1 Ir1 -162.3(12) . . . . ?
C4 C5 N1 C1 0.0 . . . . ?
C5 C6 N2 C9 -62.9(13) . . . . ?
C5 C6 N2 C7 130.7(17) . . . . ?
C5 N1 C1 O1 178.7(13) . . . . ?
C5 N1 C1 C2 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C9 N2 C7 C8 0.0 . . . . ?
N2 C6 C5 C4 -137.2(16) . . . . ?
N2 C6 C5 N1 43.3(12) . . . . ?
N2 C9 N3 C10 -174.3(15) . . . . ?
N2 C9 N3 C8 0.0 . . . . ?
N2 C7 C8 N3 0.0 . . . . ?
C7 C8 N3 C10 174.6(14) . . . . ?
C7 C8 N3 C9 0.0 . . . . ?
N3 C9 N2 C6 -168.5(19) . . . . ?
N3 C9 N2 C7 0.0 . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
