# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_p212121_a
_database_code_depnum_ccdc_archive 'CCDC 1953420'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2019-09-13 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H23 Cl Ir N O2'
_chemical_formula_weight         513.02

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'

_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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2268(3)
_cell_length_b                   14.3426(6)
_cell_length_c                   14.7546(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1740.95(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      2.761
_cell_measurement_theta_max      28.7535

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    7.831
_shelx_estimated_absorpt_T_min   0.290
_shelx_estimated_absorpt_T_max   0.407
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3603
_exptl_absorpt_correction_T_max  0.5635
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1300 (selected reflections only, before parameter refinement)
 R(int) =  0.0589(selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'PHOTON2 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25212
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.980
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3816
_reflns_number_gt                3798
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.2495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.394(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3816
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0147
_refine_ls_R_factor_gt           0.0145
_refine_ls_wR_factor_ref         0.0330
_refine_ls_wR_factor_gt          0.0330
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 1.09980(14) 0.87987(8) 0.39785(8) 0.0157(2) Uani 1 1 d . . . . .
Ir1 Ir 0.84456(2) 0.94066(2) 0.34548(2) 0.00656(4) Uani 1 1 d . . . . .
N1 N 0.9833(4) 0.9980(2) 0.2414(2) 0.0088(7) Uani 1 1 d . . . . .
O1 O 0.8571(4) 0.8308(2) 0.25132(19) 0.0125(6) Uani 1 1 d . . . . .
O2 O 0.9929(4) 0.7805(2) 0.1295(2) 0.0152(7) Uani 1 1 d . . . . .
C1 C 0.9549(5) 0.8411(3) 0.1843(3) 0.0116(9) Uani 1 1 d . . . . .
C2 C 1.0217(5) 0.9385(3) 0.1736(2) 0.0105(8) Uani 1 1 d . . . . .
C3 C 1.1151(5) 0.9652(3) 0.1004(3) 0.0147(10) Uani 1 1 d . . . . .
H3 H 1.1430 0.9215 0.0546 0.018 Uiso 1 1 calc R U . . .
C4 C 1.1674(6) 1.0568(3) 0.0947(3) 0.0169(8) Uani 1 1 d . . . . .
H4 H 1.2295 1.0773 0.0442 0.020 Uiso 1 1 calc R U . . .
C5 C 1.1279(5) 1.1178(3) 0.1637(3) 0.0140(9) Uani 1 1 d . . . . .
H5 H 1.1615 1.1811 0.1608 0.017 Uiso 1 1 calc R U . . .
C6 C 1.0392(6) 1.0861(3) 0.2370(3) 0.0123(9) Uani 1 1 d . . . . .
H6 H 1.0170 1.1277 0.2856 0.015 Uiso 1 1 calc R U . . .
C11 C 0.6798(4) 1.0541(3) 0.3724(2) 0.0082(7) Uani 1 1 d . . . . .
C12 C 0.5922(5) 0.9737(3) 0.3424(3) 0.0100(8) Uani 1 1 d . . . . .
C13 C 0.6188(5) 0.9003(3) 0.4079(3) 0.0093(9) Uani 1 1 d . . . . .
C14 C 0.7253(5) 0.9347(3) 0.4766(3) 0.0112(8) Uani 1 1 d . . . . .
C15 C 0.7684(5) 1.0295(3) 0.4533(3) 0.0112(9) Uani 1 1 d . . . . .
C16 C 0.6735(5) 1.1500(3) 0.3331(3) 0.0104(8) Uani 1 1 d . . . . .
H16A H 0.6410 1.1467 0.2685 0.013 Uiso 1 1 calc R U . . .
H16B H 0.7824 1.1792 0.3365 0.013 Uiso 1 1 calc R U . . .
C17 C 0.5496(6) 1.2093(3) 0.3864(3) 0.0149(9) Uani 1 1 d . . . . .
H17A H 0.5792 1.2084 0.4515 0.018 Uiso 1 1 calc R U . . .
H17B H 0.5562 1.2747 0.3653 0.018 Uiso 1 1 calc R U . . .
C18 C 0.3757(5) 1.1751(3) 0.3760(3) 0.0192(10) Uani 1 1 d . . . . .
H18A H 0.3426 1.1804 0.3124 0.029 Uiso 1 1 calc R U . . .
H18B H 0.3035 1.2131 0.4137 0.029 Uiso 1 1 calc R U . . .
H18C H 0.3688 1.1098 0.3951 0.029 Uiso 1 1 calc R U . . .
C19 C 0.4789(5) 0.9661(3) 0.2626(3) 0.0137(9) Uani 1 1 d . . . . .
H19A H 0.4964 0.9063 0.2320 0.021 Uiso 1 1 calc R U . . .
H19B H 0.5004 1.0172 0.2202 0.021 Uiso 1 1 calc R U . . .
H19C H 0.3662 0.9698 0.2838 0.021 Uiso 1 1 calc R U . . .
C20 C 0.5444(6) 0.8050(3) 0.4024(3) 0.0159(9) Uani 1 1 d . . . . .
H20A H 0.4279 0.8091 0.4156 0.024 Uiso 1 1 calc R U . . .
H20B H 0.5967 0.7639 0.4467 0.024 Uiso 1 1 calc R U . . .
H20C H 0.5600 0.7797 0.3413 0.024 Uiso 1 1 calc R U . . .
C21 C 0.7833(6) 0.8851(3) 0.5592(3) 0.0150(9) Uani 1 1 d . . . . .
H21A H 0.7455 0.8203 0.5578 0.023 Uiso 1 1 calc R U . . .
H21B H 0.7403 0.9162 0.6133 0.023 Uiso 1 1 calc R U . . .
H21C H 0.9024 0.8862 0.5609 0.023 Uiso 1 1 calc R U . . .
C22 C 0.8729(5) 1.0925(3) 0.5101(3) 0.0138(9) Uani 1 1 d . . . . .
H22A H 0.9108 1.1449 0.4732 0.021 Uiso 1 1 calc R U . . .
H22B H 0.9667 1.0574 0.5328 0.021 Uiso 1 1 calc R U . . .
H22C H 0.8094 1.1161 0.5614 0.021 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
Cl1 Ir1 2.4014(11) . ?
Ir1 N1 2.083(4) . ?
Ir1 O1 2.104(3) . ?
Ir1 C12 2.130(4) . ?
Ir1 C15 2.132(4) . ?
Ir1 C13 2.153(4) . ?
Ir1 C11 2.155(4) . ?
Ir1 C14 2.170(4) . ?
N1 C6 1.346(5) . ?
N1 C2 1.353(5) . ?
O1 C1 1.284(5) . ?
O2 C1 1.227(5) . ?
C1 C2 1.509(6) . ?
C2 C3 1.380(6) . ?
C3 C4 1.384(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C11 C12 1.430(6) . ?
C11 C15 1.443(6) . ?
C11 C16 1.493(5) . ?
C12 C13 1.447(6) . ?
C12 C19 1.505(6) . ?
C13 C14 1.427(6) . ?
C13 C20 1.500(6) . ?
C14 C15 1.447(6) . ?
C14 C21 1.490(6) . ?
C15 C22 1.503(6) . ?
C16 C17 1.543(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.521(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
N1 Ir1 O1 77.43(13) . . ?
N1 Ir1 C12 115.50(16) . . ?
O1 Ir1 C12 101.57(15) . . ?
N1 Ir1 C15 118.36(15) . . ?
O1 Ir1 C15 162.71(14) . . ?
C12 Ir1 C15 66.19(17) . . ?
N1 Ir1 C13 153.48(15) . . ?
O1 Ir1 C13 97.10(15) . . ?
C12 Ir1 C13 39.47(16) . . ?
C15 Ir1 C13 65.64(17) . . ?
N1 Ir1 C11 100.49(14) . . ?
O1 Ir1 C11 135.92(14) . . ?
C12 Ir1 C11 38.98(15) . . ?
C15 Ir1 C11 39.33(15) . . ?
C13 Ir1 C11 65.26(15) . . ?
N1 Ir1 C14 156.97(16) . . ?
O1 Ir1 C14 125.52(15) . . ?
C12 Ir1 C14 65.62(17) . . ?
C15 Ir1 C14 39.28(16) . . ?
C13 Ir1 C14 38.53(16) . . ?
C11 Ir1 C14 65.26(15) . . ?
N1 Ir1 Cl1 84.34(10) . . ?
O1 Ir1 Cl1 84.12(10) . . ?
C12 Ir1 Cl1 160.05(13) . . ?
C15 Ir1 Cl1 103.53(13) . . ?
C13 Ir1 Cl1 121.27(11) . . ?
C11 Ir1 Cl1 139.91(11) . . ?
C14 Ir1 Cl1 95.41(11) . . ?
C6 N1 C2 118.5(4) . . ?
C6 N1 Ir1 126.5(3) . . ?
C2 N1 Ir1 115.1(3) . . ?
C1 O1 Ir1 116.9(3) . . ?
O2 C1 O1 125.8(4) . . ?
O2 C1 C2 119.6(4) . . ?
O1 C1 C2 114.6(4) . . ?
N1 C2 C3 122.2(4) . . ?
N1 C2 C1 115.0(3) . . ?
C3 C2 C1 122.8(4) . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
N1 C6 C5 121.8(4) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C12 C11 C15 108.2(4) . . ?
C12 C11 C16 127.2(4) . . ?
C15 C11 C16 124.4(4) . . ?
C12 C11 Ir1 69.6(2) . . ?
C15 C11 Ir1 69.5(2) . . ?
C16 C11 Ir1 130.2(3) . . ?
C11 C12 C13 107.7(4) . . ?
C11 C12 C19 127.8(4) . . ?
C13 C12 C19 124.3(4) . . ?
C11 C12 Ir1 71.4(2) . . ?
C13 C12 Ir1 71.1(2) . . ?
C19 C12 Ir1 127.1(3) . . ?
C14 C13 C12 108.4(4) . . ?
C14 C13 C20 127.1(4) . . ?
C12 C13 C20 124.4(4) . . ?
C14 C13 Ir1 71.4(2) . . ?
C12 C13 Ir1 69.4(2) . . ?
C20 C13 Ir1 125.0(3) . . ?
C13 C14 C15 107.9(4) . . ?
C13 C14 C21 127.8(4) . . ?
C15 C14 C21 124.3(4) . . ?
C13 C14 Ir1 70.1(2) . . ?
C15 C14 Ir1 68.9(2) . . ?
C21 C14 Ir1 127.1(3) . . ?
C11 C15 C14 107.6(4) . . ?
C11 C15 C22 127.1(4) . . ?
C14 C15 C22 124.9(4) . . ?
C11 C15 Ir1 71.2(2) . . ?
C14 C15 Ir1 71.8(2) . . ?
C22 C15 Ir1 127.4(3) . . ?
C11 C16 C17 109.4(3) . . ?
C11 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
C11 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C16 113.1(4) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 C22 H22A 109.5 . . ?
C15 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C15 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 O1 C1 O2 170.5(3) . . . . ?
Ir1 O1 C1 C2 -11.3(5) . . . . ?
C6 N1 C2 C3 -0.3(6) . . . . ?
Ir1 N1 C2 C3 -179.0(3) . . . . ?
C6 N1 C2 C1 179.7(4) . . . . ?
Ir1 N1 C2 C1 1.0(4) . . . . ?
O2 C1 C2 N1 -174.8(4) . . . . ?
O1 C1 C2 N1 6.8(5) . . . . ?
O2 C1 C2 C3 5.1(6) . . . . ?
O1 C1 C2 C3 -173.2(4) . . . . ?
N1 C2 C3 C4 -1.9(6) . . . . ?
C1 C2 C3 C4 178.1(4) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C2 N1 C6 C5 2.8(6) . . . . ?
Ir1 N1 C6 C5 -178.7(3) . . . . ?
C4 C5 C6 N1 -3.1(7) . . . . ?
C15 C11 C12 C13 3.3(5) . . . . ?
C16 C11 C12 C13 -172.1(4) . . . . ?
Ir1 C11 C12 C13 62.2(3) . . . . ?
C15 C11 C12 C19 178.0(4) . . . . ?
C16 C11 C12 C19 2.6(7) . . . . ?
Ir1 C11 C12 C19 -123.1(5) . . . . ?
C15 C11 C12 Ir1 -58.9(3) . . . . ?
C16 C11 C12 Ir1 125.7(4) . . . . ?
C11 C12 C13 C14 -1.4(5) . . . . ?
C19 C12 C13 C14 -176.3(4) . . . . ?
Ir1 C12 C13 C14 61.1(3) . . . . ?
C11 C12 C13 C20 178.5(4) . . . . ?
C19 C12 C13 C20 3.6(7) . . . . ?
Ir1 C12 C13 C20 -119.1(4) . . . . ?
C11 C12 C13 Ir1 -62.4(3) . . . . ?
C19 C12 C13 Ir1 122.6(4) . . . . ?
C12 C13 C14 C15 -1.1(5) . . . . ?
C20 C13 C14 C15 179.1(4) . . . . ?
Ir1 C13 C14 C15 58.8(3) . . . . ?
C12 C13 C14 C21 178.1(4) . . . . ?
C20 C13 C14 C21 -1.8(7) . . . . ?
Ir1 C13 C14 C21 -122.0(4) . . . . ?
C12 C13 C14 Ir1 -59.8(3) . . . . ?
C20 C13 C14 Ir1 120.3(4) . . . . ?
C12 C11 C15 C14 -4.0(5) . . . . ?
C16 C11 C15 C14 171.6(4) . . . . ?
Ir1 C11 C15 C14 -62.9(3) . . . . ?
C12 C11 C15 C22 -177.9(4) . . . . ?
C16 C11 C15 C22 -2.3(7) . . . . ?
Ir1 C11 C15 C22 123.1(5) . . . . ?
C12 C11 C15 Ir1 59.0(3) . . . . ?
C16 C11 C15 Ir1 -125.4(4) . . . . ?
C13 C14 C15 C11 3.1(5) . . . . ?
C21 C14 C15 C11 -176.1(4) . . . . ?
Ir1 C14 C15 C11 62.5(3) . . . . ?
C13 C14 C15 C22 177.2(4) . . . . ?
C21 C14 C15 C22 -2.0(7) . . . . ?
Ir1 C14 C15 C22 -123.3(4) . . . . ?
C13 C14 C15 Ir1 -59.5(3) . . . . ?
C21 C14 C15 Ir1 121.3(4) . . . . ?
C12 C11 C16 C17 95.2(5) . . . . ?
C15 C11 C16 C17 -79.5(5) . . . . ?
Ir1 C11 C16 C17 -170.8(3) . . . . ?
C11 C16 C17 C18 -65.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 O1 0.95 2.51 3.304(5) 140.8 3_755
C6 H6 O2 0.95 2.53 3.424(5) 157.6 3_755

_refine_diff_density_max         0.615
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2014602'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 Cl4 F2 Ir2'
_chemical_formula_weight         956.75

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7487(10)
_cell_length_b                   17.713(2)
_cell_length_c                   20.308(3)
_cell_angle_alpha                73.261(4)
_cell_angle_beta                 89.913(4)
_cell_angle_gamma                83.794(4)
_cell_volume                     2994.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9710
_cell_measurement_theta_min      2.343
_cell_measurement_theta_max      36.5175

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    9.267
_shelx_estimated_absorpt_T_min   0.205
_shelx_estimated_absorpt_T_max   0.429
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0192
_exptl_absorpt_correction_T_max  0.0798
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1655 (selected reflections only, before parameter refinement)
 R(int) =  0.0786 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'PHOTON2 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40544
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.814
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             10506
_reflns_number_gt                8039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+37.7013P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10506
_refine_ls_number_parameters     694
_refine_ls_number_restraints     451
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.67316(5) 0.68648(3) 1.04377(2) 0.01153(14) Uani 1 1 d . . . . .
Ir2 Ir 0.74664(6) 0.68435(3) 0.86351(3) 0.01119(14) Uani 0.9293(9) 1 d . . P A
1
Ir3 Ir 0.75246(6) 0.31425(3) 0.45663(3) 0.01068(14) Uani 0.9293(9) 1 d . . P A
1
Ir21 Ir 0.6001(7) 0.6836(4) 0.8682(3) 0.01119(14) Uani 0.0707(9) 1 d . . P A 2
Ir31 Ir 0.8965(7) 0.3203(4) 0.4515(3) 0.01068(14) Uani 0.0707(9) 1 d . . P A 2
Ir4 Ir 0.82576(5) 0.31289(3) 0.63749(2) 0.01078(14) Uani 1 1 d . . . . .
Cl1 Cl 0.9428(4) 0.6879(2) 1.05850(19) 0.0266(8) Uani 1 1 d . . . . .
Cl2 Cl 0.4769(4) 0.6843(3) 0.84656(18) 0.0281(9) Uani 1 1 d . . . . .
Cl3 Cl 0.6861(4) 0.7794(2) 0.92878(17) 0.0237(7) Uani 1 1 d . . . . .
Cl4 Cl 0.7305(4) 0.5905(2) 0.97812(16) 0.0185(7) Uani 1 1 d . . . . .
Cl5 Cl 1.0231(4) 0.3126(3) 0.44035(19) 0.0296(9) Uani 1 1 d . . . . .
Cl6 Cl 0.5570(4) 0.3096(3) 0.65484(17) 0.0259(8) Uani 1 1 d . . . . .
Cl7 Cl 0.8124(4) 0.2194(2) 0.57012(17) 0.0224(7) Uani 1 1 d . . . . .
Cl8 Cl 0.7690(4) 0.4083(2) 0.52371(16) 0.0192(7) Uani 1 1 d . . . . .
C1 C 0.5517(16) 0.7490(10) 1.1074(7) 0.024(2) Uani 1 1 d . U . . .
C2 C 0.6250(15) 0.6719(9) 1.1506(7) 0.021(3) Uani 1 1 d . U . . .
C3 C 0.5627(15) 0.6111(9) 1.1267(7) 0.021(3) Uani 1 1 d . U . . .
C4 C 0.4507(16) 0.6545(9) 1.0711(7) 0.022(3) Uani 1 1 d . U . . .
C5 C 0.4444(15) 0.7315(10) 1.0596(7) 0.024(3) Uani 1 1 d . U . . .
C6 C 0.7377(17) 0.6613(10) 1.2057(7) 0.025(3) Uani 1 1 d . U . . .
H6A H 0.7568 0.7133 1.2098 0.038 Uiso 1 1 calc R U . . .
H6B H 0.6986 0.6299 1.2491 0.038 Uiso 1 1 calc R U . . .
H6C H 0.8338 0.6337 1.1954 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6005(17) 0.5250(10) 1.1528(7) 0.030(3) Uani 1 1 d . U . . .
H7A H 0.5406 0.4990 1.1267 0.045 Uiso 1 1 calc R U . . .
H7B H 0.7105 0.5112 1.1477 0.045 Uiso 1 1 calc R U . . .
H7C H 0.5757 0.5071 1.2016 0.045 Uiso 1 1 calc DR U . . .
C8 C 0.3530(17) 0.6092(11) 1.0333(8) 0.030(3) Uani 1 1 d . U . . .
H8A H 0.3813 0.5519 1.0523 0.045 Uiso 1 1 calc R U . . .
H8B H 0.2434 0.6221 1.0399 0.045 Uiso 1 1 calc R U . . .
H8C H 0.3735 0.6254 0.9840 0.045 Uiso 1 1 calc R U . . .
C9 C 0.3417(18) 0.7957(11) 1.0055(8) 0.034(4) Uani 1 1 d . U . . .
H9A H 0.3607 0.8483 1.0083 0.052 Uiso 1 1 calc R U . . .
H9B H 0.3657 0.7914 0.9595 0.052 Uiso 1 1 calc R U . . .
H9C H 0.2334 0.7884 1.0144 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5794(18) 0.8277(10) 1.1150(8) 0.030(3) Uani 1 1 d . U . . .
C11 C 0.6367(19) 0.8884(10) 1.0637(8) 0.031(3) Uani 1 1 d . U . . .
H11 H 0.6667 0.8795 1.0213 0.037 Uiso 1 1 calc R U . . .
C12 C 0.650(2) 0.9603(11) 1.0741(9) 0.041(3) Uani 1 1 d . U . . .
H12 H 0.6755 1.0031 1.0370 0.050 Uiso 1 1 calc R U . . .
C13 C 0.626(2) 0.9710(11) 1.1365(9) 0.042(3) Uani 1 1 d . U . . .
C14 C 0.573(2) 0.9137(12) 1.1894(10) 0.048(3) Uani 1 1 d . U . . .
H14 H 0.5523 0.9232 1.2324 0.057 Uiso 1 1 calc R U . . .
C15 C 0.549(2) 0.8404(11) 1.1793(9) 0.038(3) Uani 1 1 d . U . . .
H15 H 0.5119 0.8000 1.2155 0.046 Uiso 1 1 calc R U . . .
C21 C 0.8392(16) 0.7460(9) 0.7687(7) 0.023(3) Uani 1 1 d . U . . .
C22 C 0.9561(15) 0.7311(9) 0.8249(7) 0.019(2) Uani 1 1 d . U . . .
C23 C 0.9876(14) 0.6479(10) 0.8541(7) 0.021(3) Uani 1 1 d . U . . .
C24 C 0.8909(14) 0.6092(9) 0.8197(7) 0.019(2) Uani 1 1 d . U . . .
C25 C 0.8058(15) 0.6699(9) 0.7648(7) 0.022(3) Uani 1 1 d . U . . .
C26 C 1.0359(18) 0.7934(11) 0.8450(9) 0.034(4) Uani 1 1 d . U . . .
H26A H 0.9929 0.8464 0.8170 0.051 Uiso 1 1 calc R U . . .
H26B H 1.0199 0.7886 0.8937 0.051 Uiso 1 1 calc R U . . .
H26C H 1.1463 0.7856 0.8372 0.051 Uiso 1 1 calc R U . . .
C27 C 1.0959(16) 0.6085(10) 0.9119(8) 0.029(3) Uani 1 1 d . U . . .
H27A H 1.0969 0.5508 0.9224 0.043 Uiso 1 1 calc R U . . .
H27B H 1.1993 0.6231 0.8995 0.043 Uiso 1 1 calc R U . . .
H27C H 1.0640 0.6251 0.9523 0.043 Uiso 1 1 calc R U . . .
C28 C 0.8899(16) 0.5213(9) 0.8339(8) 0.027(3) Uani 1 1 d . U . . .
H28A H 0.8136 0.5108 0.8033 0.040 Uiso 1 1 calc R U . . .
H28B H 0.9920 0.4975 0.8259 0.040 Uiso 1 1 calc R U . . .
H28C H 0.8634 0.4982 0.8819 0.040 Uiso 1 1 calc R U . . .
C29 C 0.6929(15) 0.6572(9) 0.7133(7) 0.019(3) Uani 1 1 d . U . . .
H29A H 0.6899 0.6001 0.7209 0.028 Uiso 1 1 calc R U . . .
H29B H 0.5902 0.6819 0.7194 0.028 Uiso 1 1 calc R U . . .
H29C H 0.7258 0.6812 0.6665 0.028 Uiso 1 1 calc R U . . .
C30 C 0.781(2) 0.8244(11) 0.7189(8) 0.035(3) Uani 1 1 d . U . . .
C31 C 0.693(2) 0.8812(12) 0.7406(10) 0.051(4) Uani 1 1 d . U . . .
H31 H 0.6725 0.8724 0.7880 0.061 Uiso 1 1 calc R U . . .
C32 C 0.634(3) 0.9527(13) 0.6920(10) 0.056(4) Uani 1 1 d . U . . .
H32 H 0.5656 0.9912 0.7049 0.067 Uiso 1 1 calc R U . . .
C33 C 0.678(3) 0.9645(13) 0.6257(10) 0.058(4) Uani 1 1 d . U . . .
C34 C 0.753(3) 0.9063(12) 0.6028(10) 0.052(4) Uani 1 1 d . U . . .
H34 H 0.7676 0.9145 0.5550 0.062 Uiso 1 1 calc R U . . .
C35 C 0.810(2) 0.8342(12) 0.6502(9) 0.043(3) Uani 1 1 d . U . . .
H35 H 0.8674 0.7934 0.6356 0.052 Uiso 1 1 calc R U . . .
C41 C 0.6601(17) 0.2551(10) 0.3905(8) 0.026(3) Uani 1 1 d . U . . .
C42 C 0.6976(15) 0.3310(9) 0.3496(7) 0.019(2) Uani 1 1 d . U . . .
C43 C 0.6106(15) 0.3908(9) 0.3741(7) 0.020(2) Uani 1 1 d . U . . .
C44 C 0.5109(14) 0.3499(9) 0.4295(6) 0.019(2) Uani 1 1 d . U . . .
C45 C 0.5436(15) 0.2692(9) 0.4377(7) 0.020(2) Uani 1 1 d . U . . .
C46 C 0.8088(15) 0.3466(9) 0.2921(7) 0.020(3) Uani 1 1 d . U . . .
H46A H 0.8120 0.4039 0.2732 0.030 Uiso 1 1 calc R U . . .
H46B H 0.9115 0.3210 0.3097 0.030 Uiso 1 1 calc R U . . .
H46C H 0.7753 0.3249 0.2559 0.030 Uiso 1 1 calc R U . . .
C47 C 0.6129(18) 0.4792(10) 0.3509(7) 0.030(3) Uani 1 1 d . U . . .
H47A H 0.5405 0.5037 0.3776 0.045 Uiso 1 1 calc R U . . .
H47B H 0.7168 0.4919 0.3580 0.045 Uiso 1 1 calc R U . . .
H47C H 0.5830 0.4997 0.3020 0.045 Uiso 1 1 calc R U . . .
C48 C 0.4029(17) 0.3895(11) 0.4671(8) 0.032(4) Uani 1 1 d . U . . .
H48A H 0.4052 0.4470 0.4497 0.048 Uiso 1 1 calc R U . . .
H48B H 0.2988 0.3766 0.4607 0.048 Uiso 1 1 calc R U . . .
H48C H 0.4322 0.3715 0.5162 0.048 Uiso 1 1 calc R U . . .
C49 C 0.4632(18) 0.2071(11) 0.4887(8) 0.033(4) Uani 1 1 d . U . . .
H49A H 0.5034 0.1543 0.4861 0.049 Uiso 1 1 calc R U . . .
H49B H 0.4816 0.2106 0.5353 0.049 Uiso 1 1 calc R U . . .
H49C H 0.3524 0.2163 0.4778 0.049 Uiso 1 1 calc R U . . .
C50 C 0.717(2) 0.1781(10) 0.3786(8) 0.034(3) Uani 1 1 d . U . . .
C51 C 0.690(2) 0.1667(11) 0.3151(9) 0.043(3) Uani 1 1 d . U . . .
H51 H 0.6342 0.2081 0.2801 0.051 Uiso 1 1 calc R U . . .
C52 C 0.741(3) 0.0955(12) 0.3018(10) 0.054(4) Uani 1 1 d . U . . .
H52 H 0.7192 0.0868 0.2590 0.065 Uiso 1 1 calc R U . . .
C53 C 0.825(3) 0.0386(13) 0.3532(11) 0.065(4) Uani 1 1 d . U . . .
C54 C 0.850(3) 0.0452(13) 0.4187(11) 0.057(4) Uani 1 1 d . U . . .
H54 H 0.9014 0.0025 0.4539 0.069 Uiso 1 1 calc R U . . .
C55 C 0.796(2) 0.1157(11) 0.4311(9) 0.041(3) Uani 1 1 d . U . . .
H55 H 0.8127 0.1224 0.4752 0.049 Uiso 1 1 calc R U . . .
C61 C 0.9469(15) 0.2522(9) 0.7330(7) 0.022(2) Uani 1 1 d . U . . .
C62 C 1.0544(15) 0.2684(9) 0.6765(7) 0.021(2) Uani 1 1 d . U . . .
C63 C 1.0471(15) 0.3479(9) 0.6466(7) 0.021(2) Uani 1 1 d . U . . .
C64 C 0.9361(15) 0.3897(9) 0.6831(7) 0.020(2) Uani 1 1 d . U . . .
C65 C 0.8750(14) 0.3293(9) 0.7359(7) 0.019(2) Uani 1 1 d . U . . .
C66 C 1.1635(17) 0.2083(11) 0.6566(8) 0.032(4) Uani 1 1 d . U . . .
H66A H 1.1474 0.1550 0.6853 0.047 Uiso 1 1 calc R U . . .
H66B H 1.1450 0.2122 0.6081 0.047 Uiso 1 1 calc R U . . .
H66C H 1.2694 0.2183 0.6635 0.047 Uiso 1 1 calc R U . . .
C67 C 1.1422(17) 0.3942(11) 0.5867(8) 0.030(3) Uani 1 1 d . U . . .
H67A H 1.1102 0.4512 0.5767 0.045 Uiso 1 1 calc R U . . .
H67B H 1.2518 0.3832 0.6000 0.045 Uiso 1 1 calc R U . . .
H67C H 1.1246 0.3774 0.5457 0.045 Uiso 1 1 calc R U . . .
C68 C 0.8923(16) 0.4780(9) 0.6654(8) 0.025(3) Uani 1 1 d . U . . .
H68A H 0.9530 0.5050 0.6269 0.037 Uiso 1 1 calc R U . . .
H68B H 0.7826 0.4904 0.6524 0.037 Uiso 1 1 calc R U . . .
H68C H 0.9128 0.4962 0.7054 0.037 Uiso 1 1 calc R U . . .
C69 C 0.7590(17) 0.3408(10) 0.7867(7) 0.024(3) Uani 1 1 d . U . . .
H69A H 0.7385 0.2890 0.8168 0.036 Uiso 1 1 calc R U . . .
H69B H 0.7984 0.3719 0.8144 0.036 Uiso 1 1 calc R U . . .
H69C H 0.6635 0.3690 0.7624 0.036 Uiso 1 1 calc R U . . .
C70 C 0.9281(19) 0.1737(10) 0.7842(8) 0.029(3) Uani 1 1 d . U . . .
C71 C 0.957(2) 0.1635(10) 0.8516(8) 0.035(3) Uani 1 1 d . U . . .
H71 H 0.9865 0.2065 0.8659 0.042 Uiso 1 1 calc R U . . .
C72 C 0.944(2) 0.0894(11) 0.9018(9) 0.042(3) Uani 1 1 d . U . . .
H72 H 0.9676 0.0814 0.9491 0.050 Uiso 1 1 calc R U . . .
C73 C 0.896(3) 0.0296(11) 0.8781(9) 0.047(3) Uani 1 1 d . U . . .
C74 C 0.872(2) 0.0390(11) 0.8078(9) 0.044(3) Uani 1 1 d . U . . .
H74 H 0.8505 -0.0049 0.7927 0.052 Uiso 1 1 calc R U . . .
C75 C 0.881(2) 0.1113(9) 0.7608(8) 0.030(3) Uani 1 1 d . U . . .
H75 H 0.8554 0.1196 0.7135 0.037 Uiso 1 1 calc R U . . .
F1 F 0.6423(18) 1.0415(7) 1.1470(7) 0.071(4) Uani 1 1 d . U . . .
F2 F 0.6159(18) 1.0330(8) 0.5792(7) 0.084(4) Uani 1 1 d . U . . .
F3 F 0.888(2) -0.0306(8) 0.3395(8) 0.095(5) Uani 1 1 d . U . . .
F4 F 0.8919(19) -0.0415(7) 0.9241(6) 0.075(4) Uani 1 1 d . 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 C4 2.115(14) . ?
Ir1 C3 2.128(14) . ?
Ir1 C5 2.132(14) . ?
Ir1 C1 2.143(15) . ?
Ir1 C2 2.157(13) . ?
Ir1 Cl1 2.382(3) . ?
Ir1 Cl3 2.450(3) . ?
Ir1 Cl4 2.457(3) . ?
Ir2 C24 2.115(14) . ?
Ir2 C21 2.129(14) . ?
Ir2 C22 2.147(13) . ?
Ir2 C25 2.148(14) . ?
Ir2 C23 2.161(13) . ?
Ir2 Cl2 2.386(3) . ?
Ir2 Cl3 2.442(3) . ?
Ir2 Cl4 2.454(3) . ?
Ir3 C43 2.126(14) . ?
Ir3 C41 2.134(15) . ?
Ir3 C45 2.149(13) . ?
Ir3 C42 2.154(14) . ?
Ir3 C44 2.164(12) . ?
Ir3 Cl5 2.389(3) . ?
Ir3 Cl7 2.448(3) . ?
Ir3 Cl8 2.452(3) . ?
Ir21 Cl2 1.162(8) . ?
Ir21 Cl3 2.538(8) . ?
Ir21 Cl4 2.546(7) . ?
Ir31 Cl5 1.132(8) . ?
Ir31 Cl8 2.600(8) . ?
Ir31 Cl7 2.709(8) . ?
Ir4 C63 2.120(13) . ?
Ir4 C62 2.134(13) . ?
Ir4 C61 2.145(14) . ?
Ir4 C65 2.152(14) . ?
Ir4 C64 2.158(13) . ?
Ir4 Cl6 2.381(3) . ?
Ir4 Cl7 2.445(3) . ?
Ir4 Cl8 2.452(3) . ?
C1 C5 1.47(2) . ?
C1 C2 1.47(2) . ?
C1 C10 1.49(2) . ?
C2 C6 1.449(19) . ?
C2 C3 1.46(2) . ?
C3 C7 1.46(2) . ?
C3 C4 1.47(2) . ?
C4 C5 1.31(2) . ?
C4 C8 1.57(2) . ?
C5 C9 1.54(2) . ?
C10 C11 1.40(2) . ?
C10 C15 1.41(2) . ?
C11 C12 1.37(2) . ?
C12 C13 1.35(2) . ?
C13 F1 1.35(2) . ?
C13 C14 1.37(3) . ?
C14 C15 1.41(3) . ?
C21 C25 1.43(2) . ?
C21 C22 1.480(19) . ?
C21 C30 1.50(2) . ?
C22 C23 1.42(2) . ?
C22 C26 1.52(2) . ?
C23 C24 1.44(2) . ?
C23 C27 1.467(19) . ?
C24 C25 1.446(19) . ?
C24 C28 1.50(2) . ?
C25 C29 1.519(19) . ?
C30 C31 1.37(3) . ?
C30 C35 1.38(2) . ?
C31 C32 1.41(3) . ?
C32 C33 1.36(3) . ?
C33 C34 1.36(3) . ?
C33 F2 1.36(2) . ?
C34 C35 1.40(3) . ?
C41 C42 1.43(2) . ?
C41 C45 1.45(2) . ?
C41 C50 1.49(2) . ?
C42 C43 1.44(2) . ?
C42 C46 1.502(18) . ?
C43 C44 1.488(19) . ?
C43 C47 1.50(2) . ?
C44 C45 1.39(2) . ?
C44 C48 1.46(2) . ?
C45 C49 1.51(2) . ?
C50 C51 1.39(2) . ?
C50 C55 1.41(2) . ?
C51 C52 1.39(3) . ?
C52 C53 1.37(3) . ?
C53 C54 1.39(3) . ?
C53 F3 1.39(2) . ?
C54 C55 1.38(3) . ?
C61 C65 1.46(2) . ?
C61 C62 1.47(2) . ?
C61 C70 1.50(2) . ?
C62 C63 1.36(2) . ?
C62 C66 1.49(2) . ?
C63 C64 1.48(2) . ?
C63 C67 1.55(2) . ?
C64 C65 1.43(2) . ?
C64 C68 1.51(2) . ?
C65 C69 1.486(19) . ?
C70 C71 1.35(2) . ?
C70 C75 1.42(2) . ?
C71 C72 1.43(2) . ?
C72 C73 1.39(3) . ?
C73 F4 1.34(2) . ?
C73 C74 1.40(2) . ?
C74 C75 1.37(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 Ir1 C3 40.6(5) . . ?
C4 Ir1 C5 36.0(6) . . ?
C3 Ir1 C5 65.6(6) . . ?
C4 Ir1 C1 64.5(6) . . ?
C3 Ir1 C1 66.8(6) . . ?
C5 Ir1 C1 40.2(5) . . ?
C4 Ir1 C2 66.1(5) . . ?
C3 Ir1 C2 39.7(5) . . ?
C5 Ir1 C2 66.7(5) . . ?
C1 Ir1 C2 40.1(6) . . ?
C4 Ir1 Cl1 156.9(4) . . ?
C3 Ir1 Cl1 116.3(4) . . ?
C5 Ir1 Cl1 148.6(4) . . ?
C1 Ir1 Cl1 109.5(4) . . ?
C2 Ir1 Cl1 94.7(4) . . ?
C4 Ir1 Cl3 114.5(4) . . ?
C3 Ir1 Cl3 155.0(4) . . ?
C5 Ir1 Cl3 94.2(4) . . ?
C1 Ir1 Cl3 108.0(4) . . ?
C2 Ir1 Cl3 146.7(4) . . ?
Cl1 Ir1 Cl3 88.56(13) . . ?
C4 Ir1 Cl4 95.3(4) . . ?
C3 Ir1 Cl4 97.3(4) . . ?
C5 Ir1 Cl4 122.8(4) . . ?
C1 Ir1 Cl4 159.7(4) . . ?
C2 Ir1 Cl4 132.2(4) . . ?
Cl1 Ir1 Cl4 88.53(12) . . ?
Cl3 Ir1 Cl4 80.92(11) . . ?
C24 Ir2 C21 66.9(6) . . ?
C24 Ir2 C22 66.1(5) . . ?
C21 Ir2 C22 40.5(5) . . ?
C24 Ir2 C25 39.6(5) . . ?
C21 Ir2 C25 39.2(6) . . ?
C22 Ir2 C25 66.0(5) . . ?
C24 Ir2 C23 39.4(5) . . ?
C21 Ir2 C23 66.3(5) . . ?
C22 Ir2 C23 38.4(6) . . ?
C25 Ir2 C23 65.5(5) . . ?
C24 Ir2 Cl2 115.8(4) . . ?
C21 Ir2 Cl2 108.7(4) . . ?
C22 Ir2 Cl2 148.1(4) . . ?
C25 Ir2 Cl2 94.8(4) . . ?
C23 Ir2 Cl2 155.2(4) . . ?
C24 Ir2 Cl3 156.1(4) . . ?
C21 Ir2 Cl3 107.6(4) . . ?
C22 Ir2 Cl3 94.3(4) . . ?
C25 Ir2 Cl3 145.4(4) . . ?
C23 Ir2 Cl3 116.7(4) . . ?
Cl2 Ir2 Cl3 88.13(13) . . ?
C24 Ir2 Cl4 97.8(4) . . ?
C21 Ir2 Cl4 160.3(4) . . ?
C22 Ir2 Cl4 123.0(4) . . ?
C25 Ir2 Cl4 133.3(4) . . ?
C23 Ir2 Cl4 94.0(4) . . ?
Cl2 Ir2 Cl4 88.88(12) . . ?
Cl3 Ir2 Cl4 81.14(11) . . ?
C43 Ir3 C41 66.1(6) . . ?
C43 Ir3 C45 65.3(6) . . ?
C41 Ir3 C45 39.5(5) . . ?
C43 Ir3 C42 39.3(5) . . ?
C41 Ir3 C42 39.1(6) . . ?
C45 Ir3 C42 65.3(5) . . ?
C43 Ir3 C44 40.6(5) . . ?
C41 Ir3 C44 65.7(6) . . ?
C45 Ir3 C44 37.5(6) . . ?
C42 Ir3 C44 66.4(5) . . ?
C43 Ir3 Cl5 115.6(4) . . ?
C41 Ir3 Cl5 108.3(4) . . ?
C45 Ir3 Cl5 146.8(4) . . ?
C42 Ir3 Cl5 94.1(4) . . ?
C44 Ir3 Cl5 156.2(4) . . ?
C43 Ir3 Cl7 156.8(4) . . ?
C41 Ir3 Cl7 109.2(4) . . ?
C45 Ir3 Cl7 96.2(4) . . ?
C42 Ir3 Cl7 146.7(4) . . ?
C44 Ir3 Cl7 116.2(4) . . ?
Cl5 Ir3 Cl7 87.60(13) . . ?
C43 Ir3 Cl8 97.5(4) . . ?
C41 Ir3 Cl8 159.9(4) . . ?
C45 Ir3 Cl8 124.2(4) . . ?
C42 Ir3 Cl8 132.2(4) . . ?
C44 Ir3 Cl8 94.3(4) . . ?
Cl5 Ir3 Cl8 88.95(12) . . ?
Cl7 Ir3 Cl8 81.05(11) . . ?
Cl2 Ir21 Cl3 126.2(5) . . ?
Cl2 Ir21 Cl4 128.0(5) . . ?
Cl3 Ir21 Cl4 77.6(2) . . ?
Cl5 Ir31 Cl8 126.1(5) . . ?
Cl5 Ir31 Cl7 115.0(5) . . ?
Cl8 Ir31 Cl7 73.7(2) . . ?
C63 Ir4 C62 37.2(6) . . ?
C63 Ir4 C61 65.5(6) . . ?
C62 Ir4 C61 40.1(5) . . ?
C63 Ir4 C65 66.1(5) . . ?
C62 Ir4 C65 66.1(5) . . ?
C61 Ir4 C65 39.7(6) . . ?
C63 Ir4 C64 40.6(5) . . ?
C62 Ir4 C64 65.5(6) . . ?
C61 Ir4 C64 66.1(6) . . ?
C65 Ir4 C64 38.7(5) . . ?
C63 Ir4 Cl6 156.6(4) . . ?
C62 Ir4 Cl6 147.5(4) . . ?
C61 Ir4 Cl6 108.6(4) . . ?
C65 Ir4 Cl6 94.6(4) . . ?
C64 Ir4 Cl6 116.0(4) . . ?
C63 Ir4 Cl7 115.1(4) . . ?
C62 Ir4 Cl7 94.8(4) . . ?
C61 Ir4 Cl7 108.7(4) . . ?
C65 Ir4 Cl7 147.1(4) . . ?
C64 Ir4 Cl7 155.6(4) . . ?
Cl6 Ir4 Cl7 88.33(13) . . ?
C63 Ir4 Cl8 93.8(4) . . ?
C62 Ir4 Cl8 122.9(4) . . ?
C61 Ir4 Cl8 159.3(4) . . ?
C65 Ir4 Cl8 131.6(4) . . ?
C64 Ir4 Cl8 97.3(4) . . ?
Cl6 Ir4 Cl8 89.54(12) . . ?
Cl7 Ir4 Cl8 81.11(11) . . ?
Ir2 Cl3 Ir1 99.23(13) . . ?
Ir1 Cl3 Ir21 93.7(2) . . ?
Ir2 Cl4 Ir1 98.71(12) . . ?
Ir1 Cl4 Ir21 93.3(2) . . ?
Ir4 Cl7 Ir3 99.07(13) . . ?
Ir4 Cl7 Ir31 94.67(19) . . ?
Ir3 Cl8 Ir4 98.75(12) . . ?
Ir4 Cl8 Ir31 97.29(19) . . ?
C5 C1 C2 106.4(13) . . ?
C5 C1 C10 128.5(14) . . ?
C2 C1 C10 125.1(13) . . ?
C5 C1 Ir1 69.5(8) . . ?
C2 C1 Ir1 70.5(8) . . ?
C10 C1 Ir1 127.0(10) . . ?
C6 C2 C3 128.2(14) . . ?
C6 C2 C1 125.0(14) . . ?
C3 C2 C1 106.8(12) . . ?
C6 C2 Ir1 126.1(10) . . ?
C3 C2 Ir1 69.1(8) . . ?
C1 C2 Ir1 69.5(8) . . ?
C2 C3 C7 127.7(13) . . ?
C2 C3 C4 105.4(13) . . ?
C7 C3 C4 127.0(13) . . ?
C2 C3 Ir1 71.2(8) . . ?
C7 C3 Ir1 124.8(10) . . ?
C4 C3 Ir1 69.2(8) . . ?
C5 C4 C3 112.0(13) . . ?
C5 C4 C8 126.9(14) . . ?
C3 C4 C8 121.1(14) . . ?
C5 C4 Ir1 72.7(9) . . ?
C3 C4 Ir1 70.2(8) . . ?
C8 C4 Ir1 125.1(10) . . ?
C4 C5 C1 109.4(13) . . ?
C4 C5 C9 126.9(15) . . ?
C1 C5 C9 123.7(15) . . ?
C4 C5 Ir1 71.3(9) . . ?
C1 C5 Ir1 70.3(8) . . ?
C9 C5 Ir1 125.1(10) . . ?
C11 C10 C15 118.2(16) . . ?
C11 C10 C1 124.8(14) . . ?
C15 C10 C1 116.9(15) . . ?
C12 C11 C10 120.5(16) . . ?
C13 C12 C11 120.6(17) . . ?
C12 C13 F1 120.5(17) . . ?
C12 C13 C14 121.6(18) . . ?
F1 C13 C14 117.7(17) . . ?
C13 C14 C15 119.2(18) . . ?
C10 C15 C14 119.4(17) . . ?
C25 C21 C22 106.8(12) . . ?
C25 C21 C30 125.6(14) . . ?
C22 C21 C30 127.2(14) . . ?
C25 C21 Ir2 71.1(8) . . ?
C22 C21 Ir2 70.4(8) . . ?
C30 C21 Ir2 129.3(10) . . ?
C23 C22 C21 108.0(13) . . ?
C23 C22 C26 125.7(13) . . ?
C21 C22 C26 126.2(14) . . ?
C23 C22 Ir2 71.3(8) . . ?
C21 C22 Ir2 69.1(7) . . ?
C26 C22 Ir2 128.0(10) . . ?
C22 C23 C24 108.7(12) . . ?
C22 C23 C27 125.2(14) . . ?
C24 C23 C27 126.0(14) . . ?
C22 C23 Ir2 70.3(7) . . ?
C24 C23 Ir2 68.6(7) . . ?
C27 C23 Ir2 125.2(10) . . ?
C23 C24 C25 107.7(13) . . ?
C23 C24 C28 126.0(13) . . ?
C25 C24 C28 126.0(13) . . ?
C23 C24 Ir2 72.0(8) . . ?
C25 C24 Ir2 71.4(8) . . ?
C28 C24 Ir2 126.3(9) . . ?
C21 C25 C24 108.6(13) . . ?
C21 C25 C29 124.6(13) . . ?
C24 C25 C29 126.7(14) . . ?
C21 C25 Ir2 69.7(8) . . ?
C24 C25 Ir2 69.0(8) . . ?
C29 C25 Ir2 124.9(9) . . ?
C31 C30 C35 121.9(17) . . ?
C31 C30 C21 120.9(15) . . ?
C35 C30 C21 117.0(15) . . ?
C30 C31 C32 119.5(18) . . ?
C33 C32 C31 117.3(19) . . ?
C34 C33 C32 123(2) . . ?
C34 C33 F2 119.3(19) . . ?
C32 C33 F2 116(2) . . ?
C33 C34 C35 119.6(18) . . ?
C30 C35 C34 117.8(18) . . ?
C42 C41 C45 107.4(13) . . ?
C42 C41 C50 124.6(14) . . ?
C45 C41 C50 127.5(15) . . ?
C42 C41 Ir3 71.2(8) . . ?
C45 C41 Ir3 70.8(8) . . ?
C50 C41 Ir3 129.3(11) . . ?
C41 C42 C43 107.7(12) . . ?
C41 C42 C46 126.8(13) . . ?
C43 C42 C46 125.5(13) . . ?
C41 C42 Ir3 69.7(8) . . ?
C43 C42 Ir3 69.3(8) . . ?
C46 C42 Ir3 125.9(9) . . ?
C42 C43 C44 107.7(13) . . ?
C42 C43 C47 129.0(13) . . ?
C44 C43 C47 123.2(13) . . ?
C42 C43 Ir3 71.4(8) . . ?
C44 C43 Ir3 71.1(7) . . ?
C47 C43 Ir3 123.0(10) . . ?
C45 C44 C48 128.4(14) . . ?
C45 C44 C43 106.5(12) . . ?
C48 C44 C43 125.0(14) . . ?
C45 C44 Ir3 70.7(8) . . ?
C48 C44 Ir3 125.2(10) . . ?
C43 C44 Ir3 68.3(7) . . ?
C44 C45 C41 110.6(13) . . ?
C44 C45 C49 122.8(13) . . ?
C41 C45 C49 126.6(15) . . ?
C44 C45 Ir3 71.8(8) . . ?
C41 C45 Ir3 69.6(8) . . ?
C49 C45 Ir3 126.3(10) . . ?
C51 C50 C55 119.3(16) . . ?
C51 C50 C41 119.3(15) . . ?
C55 C50 C41 121.4(14) . . ?
C50 C51 C52 121.2(17) . . ?
C53 C52 C51 117.2(18) . . ?
C52 C53 C54 124(2) . . ?
C52 C53 F3 118.4(19) . . ?
C54 C53 F3 117.6(19) . . ?
C55 C54 C53 117.7(19) . . ?
C54 C55 C50 120.4(16) . . ?
C65 C61 C62 106.1(13) . . ?
C65 C61 C70 125.8(13) . . ?
C62 C61 C70 127.7(14) . . ?
C65 C61 Ir4 70.4(8) . . ?
C62 C61 Ir4 69.5(8) . . ?
C70 C61 Ir4 130.6(10) . . ?
C63 C62 C61 109.6(13) . . ?
C63 C62 C66 124.2(14) . . ?
C61 C62 C66 126.1(15) . . ?
C63 C62 Ir4 70.8(8) . . ?
C61 C62 Ir4 70.4(7) . . ?
C66 C62 Ir4 128.0(10) . . ?
C62 C63 C64 109.5(12) . . ?
C62 C63 C67 128.9(14) . . ?
C64 C63 C67 121.5(14) . . ?
C62 C63 Ir4 71.9(8) . . ?
C64 C63 Ir4 71.0(7) . . ?
C67 C63 Ir4 126.2(10) . . ?
C65 C64 C63 106.1(13) . . ?
C65 C64 C68 127.4(13) . . ?
C63 C64 C68 126.4(13) . . ?
C65 C64 Ir4 70.4(8) . . ?
C63 C64 Ir4 68.3(7) . . ?
C68 C64 Ir4 123.8(9) . . ?
C64 C65 C61 108.7(12) . . ?
C64 C65 C69 127.1(14) . . ?
C61 C65 C69 124.3(13) . . ?
C64 C65 Ir4 70.9(8) . . ?
C61 C65 Ir4 69.9(8) . . ?
C69 C65 Ir4 125.6(9) . . ?
C71 C70 C75 121.1(15) . . ?
C71 C70 C61 119.4(15) . . ?
C75 C70 C61 119.5(14) . . ?
C70 C71 C72 121.3(16) . . ?
C73 C72 C71 116.8(15) . . ?
F4 C73 C72 117.3(16) . . ?
F4 C73 C74 120.3(17) . . ?
C72 C73 C74 121.9(17) . . ?
C75 C74 C73 120.0(17) . . ?
C74 C75 C70 118.5(15) . . ?

_refine_diff_density_max         3.229
_refine_diff_density_min         -3.698
_refine_diff_density_rms         0.329

