# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_PDJXC7a
_database_code_depnum_ccdc_archive 'CCDC 1861852'
_audit_update_record             
;
2018-08-13 deposited with the CCDC.
2018-10-01 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            XC7
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 Cl F Ir N'
_chemical_formula_iupac          ?
_chemical_formula_weight         561.08

_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                   9.2681(5)
_cell_length_b                   10.4733(5)
_cell_length_c                   10.8722(5)
_cell_angle_alpha                82.9875(15)
_cell_angle_beta                 85.2833(17)
_cell_angle_gamma                74.7986(16)
_cell_volume                     1009.40(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9791
_cell_measurement_theta_min      2.6226
_cell_measurement_theta_max      36.3801
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent intense orange'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.113
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

_exptl_absorpt_coefficient_mu    6.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_T_max  0.52

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'I\mS microfocus source'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Photon 100 CMOS'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            61710
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_full        33.14
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             7679
_reflns_number_gt                7162
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_gt          0.0474
_refine_ls_wR_factor_ref         0.0483
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_number_reflns         7679
_refine_ls_number_parameters     249
_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)+(0.0197P)²+0.7300P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.289
_refine_diff_density_min         -0.813
_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 0.0034 0.0017 '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 0.1507 0.1611 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.3972 8.0781 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_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
Ir Ir1 0.55443(2) 0.72803(2) 0.24316(2) 0.00981(2) Uani d . . . 1 . .
Cl Cl1 0.63266(6) 0.92600(5) 0.16797(5) 0.01514(9) Uani d . . . 1 . .
F F1 1.00695(17) 0.64414(16) 0.55593(15) 0.0248(3) Uani d . . . 1 . .
N N1 0.3843(2) 0.84803(17) 0.34651(16) 0.0112(3) Uani d . . . 1 . .
C C1 0.6572(2) 0.73178(19) 0.40039(18) 0.0115(3) Uani d . . . 1 . .
C C2 0.8082(3) 0.6775(2) 0.4245(2) 0.0145(4) Uani d . . . 1 . .
H H2 0.874723 0.628051 0.365907 0.017 Uiso calc U . R 1 . .
C C3 0.8588(3) 0.6973(2) 0.5352(2) 0.0158(4) Uani d . . . 1 . .
C C4 0.7708(3) 0.7677(2) 0.6255(2) 0.0159(4) Uani d . . . 1 . .
H H4 0.811526 0.778291 0.699852 0.019 Uiso calc U . R 1 . .
C C7 0.4159(2) 0.8663(2) 0.45616(18) 0.0122(3) Uani d . . . 1 . .
H H7 0.34352 0.917528 0.509842 0.015 Uiso calc U . R 1 . .
C C6 0.5659(2) 0.8050(2) 0.49199(18) 0.0115(3) Uani d . . . 1 . .
C C5 0.6211(3) 0.8225(2) 0.60365(19) 0.0142(4) Uani d . . . 1 . .
H H5 0.556258 0.871395 0.663516 0.017 Uiso calc U . R 1 . .
C C8 0.2401(2) 0.9115(2) 0.3000(2) 0.0135(4) Uani d . . . 1 . .
C C9 0.1103(3) 0.9019(2) 0.3707(2) 0.0179(4) Uani d . . . 1 . .
H H9 0.116187 0.854836 0.451375 0.021 Uiso calc U . R 1 . .
C C10 -0.0281(3) 0.9621(3) 0.3216(3) 0.0241(5) Uani d . . . 1 . .
H H10 -0.117214 0.955127 0.368619 0.029 Uiso calc U . R 1 . .
C C11 -0.0371(3) 1.0320(3) 0.2049(3) 0.0243(5) Uani d . . . 1 . .
H H11 -0.132107 1.073808 0.172461 0.029 Uiso calc U . R 1 . .
C C12 0.0933(3) 1.0412(2) 0.1348(2) 0.0209(4) Uani d . . . 1 . .
H H12 0.087034 1.089782 0.054828 0.025 Uiso calc U . R 1 . .
C C13 0.2318(3) 0.9798(2) 0.1815(2) 0.0158(4) Uani d . . . 1 . .
H H13 0.320817 0.984117 0.132984 0.019 Uiso calc U . R 1 . .
C C14 0.4418(3) 0.5780(2) 0.2141(2) 0.0146(4) Uani d . . . 1 . .
C C15 0.4455(3) 0.6566(2) 0.0952(2) 0.0196(4) Uani d . . . 1 . .
C C16 0.5974(3) 0.6487(2) 0.0589(2) 0.0210(5) Uani d . . . 1 . .
C C17 0.6922(3) 0.5633(2) 0.1510(2) 0.0167(4) Uani d . . . 1 . .
C C18 0.5942(2) 0.5160(2) 0.24591(19) 0.0126(4) Uani d . . . 1 . .
C C19 0.3032(3) 0.5574(2) 0.2853(3) 0.0228(5) Uani d . . . 1 . .
H H19A 0.32734 0.519905 0.370439 0.034 Uiso calc U . R 1 . .
H H19B 0.263332 0.495844 0.245309 0.034 Uiso calc U . R 1 . .
H H19C 0.228184 0.642829 0.286742 0.034 Uiso calc U . R 1 . .
C C20 0.3147(4) 0.7255(3) 0.0192(3) 0.0358(8) Uani d . . . 1 . .
H H20A 0.332565 0.807435 -0.025698 0.054 Uiso calc U . R 1 . .
H H20B 0.224063 0.747526 0.073783 0.054 Uiso calc U . R 1 . .
H H20C 0.301593 0.666889 -0.040376 0.054 Uiso calc U . R 1 . .
C C21 0.6519(5) 0.7184(3) -0.0574(2) 0.0382(8) Uani d . . . 1 . .
H H21A 0.753418 0.725877 -0.047491 0.057 Uiso calc U . R 1 . .
H H21B 0.584965 0.807477 -0.073409 0.057 Uiso calc U . R 1 . .
H H21C 0.652937 0.667313 -0.127404 0.057 Uiso calc U . R 1 . .
C C22 0.8596(3) 0.5167(3) 0.1397(3) 0.0274(6) Uani d . . . 1 . .
H H22A 0.897428 0.474269 0.220202 0.041 Uiso calc U . R 1 . .
H H22B 0.901656 0.593009 0.113437 0.041 Uiso calc U . R 1 . .
H H22C 0.889275 0.452499 0.078035 0.041 Uiso calc U . R 1 . .
C C23 0.6444(3) 0.4134(2) 0.3528(2) 0.0191(4) Uani d . . . 1 . .
H H23A 0.563994 0.420652 0.41804 0.029 Uiso calc U . R 1 . .
H H23B 0.733422 0.427977 0.385707 0.029 Uiso calc U . R 1 . .
H H23C 0.668509 0.324531 0.324566 0.029 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
Ir1 C1 . 2.033(2) ?
Ir1 N1 . 2.0842(18) ?
Ir1 C18 . 2.150(2) ?
Ir1 C17 . 2.160(2) ?
Ir1 C14 . 2.167(2) ?
Ir1 C16 . 2.228(2) ?
Ir1 C15 . 2.264(2) ?
Ir1 Cl1 . 2.4021(5) ?
F1 C3 . 1.365(3) ?
N1 C7 . 1.299(3) ?
N1 C8 . 1.430(3) ?
C1 C2 . 1.399(3) ?
C1 C6 . 1.415(3) ?
C2 C3 . 1.385(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.379(3) ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.95 ?
C7 C6 . 1.434(3) ?
C7 H7 . 0.95 ?
C6 C5 . 1.405(3) ?
C5 H5 . 0.95 ?
C8 C13 . 1.393(3) ?
C8 C9 . 1.393(3) ?
C9 C10 . 1.391(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.383(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.393(4) ?
C11 H11 . 0.95 ?
C12 C13 . 1.384(3) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 C18 . 1.442(3) ?
C14 C15 . 1.448(3) ?
C14 C19 . 1.495(3) ?
C15 C16 . 1.415(4) ?
C15 C20 . 1.495(4) ?
C16 C17 . 1.445(4) ?
C16 C21 . 1.500(3) ?
C17 C18 . 1.446(3) ?
C17 C22 . 1.499(4) ?
C18 C23 . 1.498(3) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?

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
C1 Ir1 N1 . . 77.75(8) ?
C1 Ir1 C18 . . 98.49(8) ?
N1 Ir1 C18 . . 124.96(7) ?
C1 Ir1 C17 . . 106.48(9) ?
N1 Ir1 C17 . . 163.46(8) ?
C18 Ir1 C17 . . 39.21(8) ?
C1 Ir1 C14 . . 124.57(8) ?
N1 Ir1 C14 . . 98.87(8) ?
C18 Ir1 C14 . . 39.03(8) ?
C17 Ir1 C14 . . 65.35(9) ?
C1 Ir1 C16 . . 141.89(10) ?
N1 Ir1 C16 . . 140.32(9) ?
C18 Ir1 C16 . . 64.01(8) ?
C17 Ir1 C16 . . 38.41(9) ?
C14 Ir1 C16 . . 63.38(9) ?
C1 Ir1 C15 . . 161.69(8) ?
N1 Ir1 C15 . . 107.42(9) ?
C18 Ir1 C15 . . 63.93(8) ?
C17 Ir1 C15 . . 63.74(9) ?
C14 Ir1 C15 . . 38.08(8) ?
C16 Ir1 C15 . . 36.72(10) ?
C1 Ir1 Cl1 . . 85.69(6) ?
N1 Ir1 Cl1 . . 87.05(5) ?
C18 Ir1 Cl1 . . 147.93(6) ?
C17 Ir1 Cl1 . . 109.04(6) ?
C14 Ir1 Cl1 . . 149.74(6) ?
C16 Ir1 Cl1 . . 93.30(6) ?
C15 Ir1 Cl1 . . 111.82(6) ?
C7 N1 C8 . . 120.48(18) ?
C7 N1 Ir1 . . 116.69(15) ?
C8 N1 Ir1 . . 122.81(13) ?
C2 C1 C6 . . 117.03(19) ?
C2 C1 Ir1 . . 127.47(15) ?
C6 C1 Ir1 . . 115.38(15) ?
C3 C2 C1 . . 118.8(2) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
F1 C3 C4 . . 117.7(2) ?
F1 C3 C2 . . 117.6(2) ?
C4 C3 C2 . . 124.7(2) ?
C3 C4 C5 . . 117.6(2) ?
C3 C4 H4 . . 121.2 ?
C5 C4 H4 . . 121.2 ?
N1 C7 C6 . . 116.52(18) ?
N1 C7 H7 . . 121.7 ?
C6 C7 H7 . . 121.7 ?
C5 C6 C1 . . 122.7(2) ?
C5 C6 C7 . . 123.60(19) ?
C1 C6 C7 . . 113.62(18) ?
C4 C5 C6 . . 119.3(2) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C13 C8 C9 . . 120.6(2) ?
C13 C8 N1 . . 118.8(2) ?
C9 C8 N1 . . 120.50(19) ?
C10 C9 C8 . . 119.0(2) ?
C10 C9 H9 . . 120.5 ?
C8 C9 H9 . . 120.5 ?
C11 C10 C9 . . 120.6(2) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C12 . . 120.0(2) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C13 C12 C11 . . 120.1(2) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C8 . . 119.6(2) ?
C12 C13 H13 . . 120.2 ?
C8 C13 H13 . . 120.2 ?
C18 C14 C15 . . 108.0(2) ?
C18 C14 C19 . . 126.6(2) ?
C15 C14 C19 . . 125.3(2) ?
C18 C14 Ir1 . . 69.85(12) ?
C15 C14 Ir1 . . 74.58(12) ?
C19 C14 Ir1 . . 124.84(15) ?
C16 C15 C14 . . 107.5(2) ?
C16 C15 C20 . . 125.6(2) ?
C14 C15 C20 . . 126.8(3) ?
C16 C15 Ir1 . . 70.26(13) ?
C14 C15 Ir1 . . 67.34(12) ?
C20 C15 Ir1 . . 131.06(17) ?
C15 C16 C17 . . 109.62(19) ?
C15 C16 C21 . . 125.2(3) ?
C17 C16 C21 . . 125.2(3) ?
C15 C16 Ir1 . . 73.02(13) ?
C17 C16 Ir1 . . 68.26(12) ?
C21 C16 Ir1 . . 125.07(17) ?
C16 C17 C18 . . 106.8(2) ?
C16 C17 C22 . . 126.0(2) ?
C18 C17 C22 . . 126.6(2) ?
C16 C17 Ir1 . . 73.33(13) ?
C18 C17 Ir1 . . 70.01(11) ?
C22 C17 Ir1 . . 128.72(17) ?
C14 C18 C17 . . 107.95(19) ?
C14 C18 C23 . . 126.6(2) ?
C17 C18 C23 . . 125.3(2) ?
C14 C18 Ir1 . . 71.12(11) ?
C17 C18 Ir1 . . 70.77(12) ?
C23 C18 Ir1 . . 126.93(15) ?
C14 C19 H19A . . 109.5 ?
C14 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C14 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C15 C20 H20A . . 109.5 ?
C15 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C15 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C16 C21 H21A . . 109.5 ?
C16 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C16 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C17 C22 H22A . . 109.5 ?
C17 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C17 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C18 C23 H23A . . 109.5 ?
C18 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C18 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.5(3) ?
Ir1 C1 C2 C3 . . . . 176.28(16) ?
C1 C2 C3 F1 . . . . -179.49(19) ?
C1 C2 C3 C4 . . . . -0.1(3) ?
F1 C3 C4 C5 . . . . 179.41(19) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
C8 N1 C7 C6 . . . . -176.44(18) ?
Ir1 N1 C7 C6 . . . . 1.9(2) ?
C2 C1 C6 C5 . . . . -0.8(3) ?
Ir1 C1 C6 C5 . . . . -177.12(16) ?
C2 C1 C6 C7 . . . . 175.23(18) ?
Ir1 C1 C6 C7 . . . . -1.1(2) ?
N1 C7 C6 C5 . . . . 175.48(19) ?
N1 C7 C6 C1 . . . . -0.5(3) ?
C3 C4 C5 C6 . . . . -0.4(3) ?
C1 C6 C5 C4 . . . . 0.8(3) ?
C7 C6 C5 C4 . . . . -174.9(2) ?
C7 N1 C8 C13 . . . . 130.8(2) ?
Ir1 N1 C8 C13 . . . . -47.4(2) ?
C7 N1 C8 C9 . . . . -51.0(3) ?
Ir1 N1 C8 C9 . . . . 130.82(18) ?
C13 C8 C9 C10 . . . . -0.3(3) ?
N1 C8 C9 C10 . . . . -178.5(2) ?
C8 C9 C10 C11 . . . . -0.8(4) ?
C9 C10 C11 C12 . . . . 0.8(4) ?
C10 C11 C12 C13 . . . . 0.4(4) ?
C11 C12 C13 C8 . . . . -1.6(3) ?
C9 C8 C13 C12 . . . . 1.5(3) ?
N1 C8 C13 C12 . . . . 179.7(2) ?
C18 C14 C15 C16 . . . . -3.3(2) ?
C19 C14 C15 C16 . . . . -179.0(2) ?
Ir1 C14 C15 C16 . . . . 58.97(15) ?
C18 C14 C15 C20 . . . . 172.5(2) ?
C19 C14 C15 C20 . . . . -3.2(4) ?
Ir1 C14 C15 C20 . . . . -125.2(2) ?
C18 C14 C15 Ir1 . . . . -62.26(14) ?
C19 C14 C15 Ir1 . . . . 122.1(2) ?
C14 C15 C16 C17 . . . . 1.5(2) ?
C20 C15 C16 C17 . . . . -174.4(2) ?
Ir1 C15 C16 C17 . . . . 58.67(15) ?
C14 C15 C16 C21 . . . . -178.5(2) ?
C20 C15 C16 C21 . . . . 5.6(4) ?
Ir1 C15 C16 C21 . . . . -121.3(2) ?
C14 C15 C16 Ir1 . . . . -57.15(14) ?
C20 C15 C16 Ir1 . . . . 127.0(2) ?
C15 C16 C17 C18 . . . . 0.8(2) ?
C21 C16 C17 C18 . . . . -179.2(2) ?
Ir1 C16 C17 C18 . . . . 62.41(14) ?
C15 C16 C17 C22 . . . . 172.3(2) ?
C21 C16 C17 C22 . . . . -7.7(4) ?
Ir1 C16 C17 C22 . . . . -126.1(2) ?
C15 C16 C17 Ir1 . . . . -61.58(16) ?
C21 C16 C17 Ir1 . . . . 118.4(2) ?
C15 C14 C18 C17 . . . . 3.8(2) ?
C19 C14 C18 C17 . . . . 179.4(2) ?
Ir1 C14 C18 C17 . . . . -61.54(14) ?
C15 C14 C18 C23 . . . . -172.2(2) ?
C19 C14 C18 C23 . . . . 3.4(3) ?
Ir1 C14 C18 C23 . . . . 122.5(2) ?
C15 C14 C18 Ir1 . . . . 65.35(14) ?
C19 C14 C18 Ir1 . . . . -119.0(2) ?
C16 C17 C18 C14 . . . . -2.9(2) ?
C22 C17 C18 C14 . . . . -174.3(2) ?
Ir1 C17 C18 C14 . . . . 61.76(14) ?
C16 C17 C18 C23 . . . . 173.2(2) ?
C22 C17 C18 C23 . . . . 1.8(4) ?
Ir1 C17 C18 C23 . . . . -122.2(2) ?
C16 C17 C18 Ir1 . . . . -64.62(14) ?
C22 C17 C18 Ir1 . . . . 124.0(2) ?

