# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Tbut
_database_code_depnum_ccdc_archive 'CCDC 1437713'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_audit_creation_date             2015-11-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H39 Cl Ir N2, 1(Cl)'
_chemical_formula_sum            'C28 H39 Cl2 Ir N2'
_chemical_formula_weight         666.71
_chemical_absolute_configuration .
_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'
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'

_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      trigonal
_space_group_IT_number           159
_space_group_name_H-M_alt        'P 3 1 c'
_space_group_name_Hall           'P 3 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, z+1/2'

_cell_length_a                   16.6890(11)
_cell_length_b                   16.6890(11)
_cell_length_c                   21.5798(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5205.2(8)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.526
_cell_measurement_theta_min      2.356
_shelx_estimated_absorpt_T_max   0.479
_shelx_estimated_absorpt_T_min   0.430
_exptl_absorpt_coefficient_mu    4.016
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1764 before and 0.0817 after correction.
The Ratio of minimum to maximum transmission is 0.5687.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Yellow Orange'
_exptl_crystal_colour_modifier   Yellow
_exptl_crystal_colour_primary    Orange
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1992
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.215
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            73836
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_min         1.409
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6435
_reflns_number_total             7113
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         7113
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0600
_refine_special_details          
;
 Refined as a 4-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.713(14) 0.008(8) 0.008(9) 0.271(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Fixed Sof: Cl4(0.33333) Cl3(0.33333)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C7(H7), C9(H9), C10(H10)
4.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.36694(2) 0.26254(2) 0.57139(2) 0.02851(8) Uani 1 1 d . . . . .
Cl1 Cl 0.46442(17) 0.39453(15) 0.63303(10) 0.0337(5) Uani 1 1 d . . . . .
N1 N 0.4018(5) 0.3568(5) 0.4979(3) 0.0322(18) Uani 1 1 d . . . . .
N2 N 0.2752(4) 0.3122(5) 0.5804(3) 0.0249(16) Uani 1 1 d . . . . .
C1 C 0.4660(7) 0.3727(6) 0.4543(4) 0.034(2) Uani 1 1 d . . . . .
H1 H 0.4952 0.3363 0.4551 0.041 Uiso 1 1 calc R . . . .
C2 C 0.4910(7) 0.4377(7) 0.4095(3) 0.032(2) Uani 1 1 d . . . . .
H2 H 0.5369 0.4464 0.3800 0.039 Uiso 1 1 calc R . . . .
C3 C 0.4488(6) 0.4919(6) 0.4068(3) 0.030(2) Uani 1 1 d . . . . .
C4 C 0.3817(6) 0.4747(6) 0.4524(4) 0.0284(19) Uani 1 1 d . . . . .
H4 H 0.3512 0.5099 0.4526 0.034 Uiso 1 1 calc R . . . .
C5 C 0.3603(6) 0.4090(6) 0.4959(4) 0.0257(19) Uani 1 1 d . . . . .
C6 C 0.2893(6) 0.3843(6) 0.5451(4) 0.0269(18) Uani 1 1 d . . . . .
C7 C 0.2418(6) 0.4320(7) 0.5546(3) 0.029(2) Uani 1 1 d . . . . .
H7 H 0.2546 0.4838 0.5294 0.035 Uiso 1 1 calc R . . . .
C8 C 0.1753(6) 0.4033(6) 0.6010(4) 0.027(2) Uani 1 1 d . . . . .
C9 C 0.1608(6) 0.3263(6) 0.6364(4) 0.0277(19) Uani 1 1 d . . . . .
H9 H 0.1161 0.3040 0.6687 0.033 Uiso 1 1 calc R . . . .
C10 C 0.2104(6) 0.2836(6) 0.6246(4) 0.0276(19) Uani 1 1 d . . . . .
H10 H 0.1986 0.2313 0.6488 0.033 Uiso 1 1 calc R . . . .
C11 C 0.4730(6) 0.5648(6) 0.3557(4) 0.032(2) Uani 1 1 d . . . . .
C12 C 0.5313(8) 0.5585(8) 0.3065(4) 0.053(3) Uani 1 1 d . . . . .
H12A H 0.5943 0.5824 0.3222 0.080 Uiso 1 1 calc GR . . . .
H12B H 0.5327 0.5952 0.2706 0.080 Uiso 1 1 calc GR . . . .
H12C H 0.5055 0.4937 0.2941 0.080 Uiso 1 1 calc GR . . . .
C13 C 0.3861(7) 0.5575(9) 0.3260(5) 0.051(3) Uani 1 1 d . . . . .
H13A H 0.3611 0.5074 0.2953 0.077 Uiso 1 1 calc GR . . . .
H13B H 0.4021 0.6160 0.3055 0.077 Uiso 1 1 calc GR . . . .
H13C H 0.3396 0.5443 0.3581 0.077 Uiso 1 1 calc GR . . . .
C14 C 0.5288(7) 0.6623(7) 0.3868(4) 0.043(2) Uani 1 1 d . . . . .
H14A H 0.4920 0.6674 0.4203 0.064 Uiso 1 1 calc GR . . . .
H14B H 0.5427 0.7104 0.3558 0.064 Uiso 1 1 calc GR . . . .
H14C H 0.5868 0.6701 0.4038 0.064 Uiso 1 1 calc GR . . . .
C15 C 0.1216(6) 0.4528(6) 0.6130(4) 0.027(2) Uani 1 1 d . . . . .
C16 C 0.0629(6) 0.4397(6) 0.5539(4) 0.032(2) Uani 1 1 d . . . . .
H16A H 0.1037 0.4632 0.5178 0.048 Uiso 1 1 calc GR . . . .
H16B H 0.0296 0.4738 0.5587 0.048 Uiso 1 1 calc GR . . . .
H16C H 0.0184 0.3738 0.5481 0.048 Uiso 1 1 calc GR . . . .
C17 C 0.0585(7) 0.4159(7) 0.6687(4) 0.034(2) Uani 1 1 d . . . . .
H17A H 0.0113 0.3512 0.6614 0.051 Uiso 1 1 calc GR . . . .
H17B H 0.0284 0.4528 0.6754 0.051 Uiso 1 1 calc GR . . . .
H17C H 0.0948 0.4198 0.7054 0.051 Uiso 1 1 calc GR . . . .
C18 C 0.1882(7) 0.5551(7) 0.6239(4) 0.035(2) Uani 1 1 d . . . . .
H18A H 0.2326 0.5625 0.6563 0.053 Uiso 1 1 calc GR . . . .
H18B H 0.1535 0.5853 0.6369 0.053 Uiso 1 1 calc GR . . . .
H18C H 0.2216 0.5836 0.5854 0.053 Uiso 1 1 calc GR . . . .
C19 C 0.3399(9) 0.1374(8) 0.5239(6) 0.046(3) Uani 1 1 d . . . . .
C20 C 0.2725(6) 0.1136(5) 0.5742(7) 0.039(2) Uani 1 1 d . . . . .
C21 C 0.3225(8) 0.1440(7) 0.6303(5) 0.037(3) Uani 1 1 d . . . . .
C22 C 0.4186(8) 0.1817(7) 0.6179(5) 0.038(3) Uani 1 1 d . . . . .
C23 C 0.4312(8) 0.1798(7) 0.5546(5) 0.043(3) Uani 1 1 d . . . . .
C24 C 0.1687(7) 0.0645(7) 0.5689(8) 0.065(3) Uani 1 1 d . . . . .
H24A H 0.1440 0.0913 0.5984 0.097 Uiso 1 1 calc GR . . . .
H24B H 0.1430 -0.0014 0.5781 0.097 Uiso 1 1 calc GR . . . .
H24C H 0.1513 0.0714 0.5267 0.097 Uiso 1 1 calc GR . . . .
C25 C 0.2825(10) 0.1297(9) 0.6951(5) 0.064(4) Uani 1 1 d . . . . .
H25A H 0.3138 0.1883 0.7179 0.095 Uiso 1 1 calc GR . . . .
H25B H 0.2916 0.0833 0.7168 0.095 Uiso 1 1 calc GR . . . .
H25C H 0.2162 0.1083 0.6925 0.095 Uiso 1 1 calc GR . . . .
C26 C 0.4960(9) 0.2168(9) 0.6661(7) 0.073(4) Uani 1 1 d . . . . .
H26A H 0.5451 0.2790 0.6546 0.110 Uiso 1 1 calc GR . . . .
H26B H 0.5213 0.1750 0.6677 0.110 Uiso 1 1 calc GR . . . .
H26C H 0.4711 0.2188 0.7068 0.110 Uiso 1 1 calc GR . . . .
C27 C 0.5184(9) 0.2049(9) 0.5207(7) 0.074(4) Uani 1 1 d . . . . .
H27A H 0.5266 0.2476 0.4869 0.111 Uiso 1 1 calc GR . . . .
H27B H 0.5148 0.1488 0.5035 0.111 Uiso 1 1 calc GR . . . .
H27C H 0.5709 0.2347 0.5492 0.111 Uiso 1 1 calc GR . . . .
C28 C 0.3207(10) 0.1165(8) 0.4575(5) 0.062(4) Uani 1 1 d . . . . .
H28A H 0.2864 0.1457 0.4417 0.093 Uiso 1 1 calc GR . . . .
H28B H 0.2837 0.0494 0.4517 0.093 Uiso 1 1 calc GR . . . .
H28C H 0.3792 0.1405 0.4349 0.093 Uiso 1 1 calc GR . . . .
Cl4 Cl 0.6156(11) 0.2873(8) 0.3806(5) 0.096(5) Uani 0.3333 1 d . . . . .
Cl3 Cl 0.0636(7) 0.1187(8) 0.7276(5) 0.076(3) Uani 0.3333 1 d . . . . .
Cl2 Cl 0.3333 0.6667 0.47571(16) 0.0271(8) Uani 1 3 d S T 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 2.384(2) . ?
Ir1 N1 2.101(8) . ?
Ir1 N2 2.083(6) . ?
Ir1 C19 2.162(11) . ?
Ir1 C20 2.179(7) . ?
Ir1 C21 2.148(10) . ?
Ir1 C22 2.175(10) . ?
Ir1 C23 2.161(10) . ?
N1 C1 1.348(11) . ?
N1 C5 1.358(11) . ?
N2 C6 1.341(10) . ?
N2 C10 1.338(11) . ?
C1 H1 0.9500 . ?
C1 C2 1.354(12) . ?
C2 H2 0.9500 . ?
C2 C3 1.399(12) . ?
C3 C4 1.408(11) . ?
C3 C11 1.539(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.347(12) . ?
C5 C6 1.488(11) . ?
C6 C7 1.390(11) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(11) . ?
C8 C9 1.409(12) . ?
C8 C15 1.514(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.359(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.480(13) . ?
C11 C13 1.534(13) . ?
C11 C14 1.564(13) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.555(11) . ?
C15 C17 1.512(12) . ?
C15 C18 1.520(13) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.468(17) . ?
C19 C23 1.479(17) . ?
C19 C28 1.471(17) . ?
C20 C21 1.413(17) . ?
C20 C24 1.506(13) . ?
C21 C22 1.425(17) . ?
C21 C25 1.517(14) . ?
C22 C23 1.384(15) . ?
C22 C26 1.528(16) . ?
C23 C27 1.489(15) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
Cl4 Cl4 1.41(2) 2_655 ?
Cl4 Cl4 1.41(2) 3_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 Cl1 85.6(2) . . ?
N1 Ir1 C19 102.2(4) . . ?
N1 Ir1 C20 130.3(5) . . ?
N1 Ir1 C21 167.3(3) . . ?
N1 Ir1 C22 139.9(4) . . ?
N1 Ir1 C23 108.2(3) . . ?
N2 Ir1 Cl1 83.0(2) . . ?
N2 Ir1 N1 75.9(3) . . ?
N2 Ir1 C19 126.1(4) . . ?
N2 Ir1 C20 101.3(3) . . ?
N2 Ir1 C21 109.1(3) . . ?
N2 Ir1 C22 143.3(4) . . ?
N2 Ir1 C23 165.6(4) . . ?
C19 Ir1 Cl1 150.9(4) . . ?
C19 Ir1 C20 39.5(5) . . ?
C19 Ir1 C22 64.9(4) . . ?
C20 Ir1 Cl1 144.0(4) . . ?
C21 Ir1 Cl1 106.4(3) . . ?
C21 Ir1 C19 65.3(4) . . ?
C21 Ir1 C20 38.1(5) . . ?
C21 Ir1 C22 38.5(5) . . ?
C21 Ir1 C23 64.1(4) . . ?
C22 Ir1 Cl1 91.0(3) . . ?
C22 Ir1 C20 64.2(4) . . ?
C23 Ir1 Cl1 110.9(3) . . ?
C23 Ir1 C19 40.0(5) . . ?
C23 Ir1 C20 65.3(4) . . ?
C23 Ir1 C22 37.2(4) . . ?
C1 N1 Ir1 124.7(6) . . ?
C1 N1 C5 117.5(7) . . ?
C5 N1 Ir1 117.7(6) . . ?
C6 N2 Ir1 118.0(5) . . ?
C10 N2 Ir1 123.3(6) . . ?
C10 N2 C6 118.2(7) . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.5(8) . . ?
C2 C1 H1 118.2 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(8) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 116.5(7) . . ?
C2 C3 C11 121.6(7) . . ?
C4 C3 C11 121.9(8) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(8) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C6 112.9(7) . . ?
C4 C5 N1 122.1(7) . . ?
C4 C5 C6 125.0(8) . . ?
N2 C6 C5 114.3(7) . . ?
N2 C6 C7 122.4(7) . . ?
C7 C6 C5 123.3(8) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.6(8) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 116.6(8) . . ?
C7 C8 C15 121.6(7) . . ?
C9 C8 C15 121.8(8) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(8) . . ?
C10 C9 H9 119.9 . . ?
N2 C10 C9 122.9(7) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C3 C11 C14 107.5(7) . . ?
C12 C11 C3 112.3(8) . . ?
C12 C11 C13 108.8(7) . . ?
C12 C11 C14 108.1(8) . . ?
C13 C11 C3 111.9(8) . . ?
C13 C11 C14 108.1(8) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 . . ?
C8 C15 C16 106.6(6) . . ?
C8 C15 C18 109.9(7) . . ?
C17 C15 C8 113.3(7) . . ?
C17 C15 C16 109.4(7) . . ?
C17 C15 C18 107.7(7) . . ?
C18 C15 C16 109.9(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 Ir1 70.9(5) . . ?
C20 C19 C23 105.3(10) . . ?
C20 C19 C28 127.5(12) . . ?
C23 C19 Ir1 70.0(6) . . ?
C28 C19 Ir1 127.3(8) . . ?
C28 C19 C23 126.9(11) . . ?
C19 C20 Ir1 69.6(5) . . ?
C19 C20 C24 127.5(14) . . ?
C21 C20 Ir1 69.7(5) . . ?
C21 C20 C19 107.6(9) . . ?
C21 C20 C24 124.9(13) . . ?
C24 C20 Ir1 126.7(6) . . ?
C20 C21 Ir1 72.2(5) . . ?
C20 C21 C22 109.2(9) . . ?
C20 C21 C25 126.9(12) . . ?
C22 C21 Ir1 71.8(6) . . ?
C22 C21 C25 123.5(11) . . ?
C25 C21 Ir1 127.8(7) . . ?
C21 C22 Ir1 69.7(6) . . ?
C21 C22 C26 126.2(11) . . ?
C23 C22 Ir1 70.8(7) . . ?
C23 C22 C21 109.0(11) . . ?
C23 C22 C26 124.8(12) . . ?
C26 C22 Ir1 126.7(7) . . ?
C19 C23 Ir1 70.0(6) . . ?
C19 C23 C27 122.8(10) . . ?
C22 C23 Ir1 72.0(6) . . ?
C22 C23 C19 108.7(11) . . ?
C22 C23 C27 128.1(12) . . ?
C27 C23 Ir1 129.0(7) . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C19 C28 H28A 109.5 . . ?
C19 C28 H28B 109.5 . . ?
C19 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
Cl4 Cl4 Cl4 59.999(3) 2_655 3_665 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.713(14)
2 0.008(8)
3 0.008(9)
4 0.271(8)

####################################################################### 
# 
# 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_KubASCF3
_database_code_depnum_ccdc_archive 'CCDC 1437714'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_audit_creation_date             2015-11-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 Cl F6 Ir N2, Cl, 0.5(H2 O)'
_chemical_formula_sum            'C22 H22 Cl2 F6 Ir N2 O0.50'
_chemical_formula_weight         699.51
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   16.2237(5)
_cell_length_b                   15.7371(4)
_cell_length_c                   21.8522(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.000(2)
_cell_angle_gamma                90
_cell_volume                     5275.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      24.453
_cell_measurement_theta_min      2.294
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.321
_exptl_absorpt_correction_T_max  0.0452
_exptl_absorpt_correction_T_min  0.0239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.5288.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Yellow Orange'
_exptl_crystal_colour_modifier   Yellow
_exptl_crystal_colour_primary    Orange
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             2696
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.067
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            68790
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         1.627
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8428
_reflns_number_total             10796
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         2.159
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         10796
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+5.4695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0788
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O1S-H1SB = O1S-H1SA
 0.95 with sigma of 0.02
 H1SA-H1SB
 1.5 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C7(H7), C9(H9), C10(H10), C1'(H1'), C2'(H2'),
 C4'(H4'), C7'(H7'), C9'(H9'), C10'(H10')
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C18'(H18D,H18E,H18F), C19'(H19D,H19E,H19F),
 C20'(H20D,H20E,H20F), C21'(H21D,H21E,H21F), C22'(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.78769(2) 0.93879(2) 0.25620(2) 0.02521(6) Uani 1 1 d . . . . .
Cl1 Cl 0.89715(8) 1.02547(8) 0.32841(7) 0.0332(3) Uani 1 1 d . . . . .
F1 F 0.6747(2) 1.0510(2) 0.52097(17) 0.0577(10) Uani 1 1 d . . . . .
F2 F 0.5466(2) 1.0691(2) 0.45286(17) 0.0485(9) Uani 1 1 d . . . . .
F3 F 0.5863(2) 0.9458(2) 0.49418(19) 0.0591(10) Uani 1 1 d . . . . .
F4 F 0.8865(3) 0.6631(3) 0.5212(2) 0.0716(13) Uani 1 1 d . . . . .
F5 F 0.9101(4) 0.5804(2) 0.4521(2) 0.0950(17) Uani 1 1 d . . . . .
F6 F 1.0071(2) 0.6644(3) 0.5053(2) 0.0735(13) Uani 1 1 d . . . . .
N1 N 0.7198(2) 0.9609(2) 0.32075(19) 0.0243(9) Uani 1 1 d . . . . .
N2 N 0.8333(2) 0.8438(2) 0.3260(2) 0.0248(9) Uani 1 1 d . . . . .
C1 C 0.6634(3) 1.0253(3) 0.3154(3) 0.0287(12) Uani 1 1 d . . . . .
H1 H 0.6488 1.0598 0.2778 0.034 Uiso 1 1 calc R . . . .
C2 C 0.6260(3) 1.0434(3) 0.3620(3) 0.0303(12) Uani 1 1 d . . . . .
H2 H 0.5855 1.0888 0.3562 0.036 Uiso 1 1 calc R . . . .
C3 C 0.6482(3) 0.9946(3) 0.4168(3) 0.0300(12) Uani 1 1 d . . . . .
C4 C 0.7052(3) 0.9267(3) 0.4239(3) 0.0299(12) Uani 1 1 d . . . . .
H4 H 0.7198 0.8915 0.4612 0.036 Uiso 1 1 calc R . . . .
C5 C 0.7402(3) 0.9116(3) 0.3750(2) 0.0265(11) Uani 1 1 d . . . . .
C6 C 0.8027(3) 0.8437(3) 0.3767(2) 0.0256(11) Uani 1 1 d . . . . .
C7 C 0.8304(3) 0.7842(3) 0.4265(3) 0.0296(12) Uani 1 1 d . . . . .
H7 H 0.8083 0.7854 0.4618 0.036 Uiso 1 1 calc R . . . .
C8 C 0.8906(3) 0.7233(3) 0.4236(3) 0.0285(12) Uani 1 1 d . . . . .
C9 C 0.9219(3) 0.7242(3) 0.3716(2) 0.0278(11) Uani 1 1 d . . . . .
H9 H 0.9636 0.6832 0.3691 0.033 Uiso 1 1 calc R . . . .
C10 C 0.8927(3) 0.7841(3) 0.3241(2) 0.0261(11) Uani 1 1 d . . . . .
H10 H 0.9147 0.7838 0.2888 0.031 Uiso 1 1 calc R . . . .
C11 C 0.6136(4) 1.0147(4) 0.4715(3) 0.0437(15) Uani 1 1 d . . . . .
C12 C 0.9217(4) 0.6578(4) 0.4756(3) 0.0402(14) Uani 1 1 d . . . . .
C13 C 0.7196(3) 1.0077(3) 0.1684(2) 0.0312(12) Uani 1 1 d . . . . .
C14 C 0.6796(3) 0.9254(3) 0.1677(3) 0.0325(13) Uani 1 1 d . . . . .
C15 C 0.7434(4) 0.8614(4) 0.1699(3) 0.0348(13) Uani 1 1 d . . . . .
C16 C 0.8234(3) 0.9050(3) 0.1719(2) 0.0328(13) Uani 1 1 d . . . . .
C17 C 0.8069(4) 0.9940(3) 0.1692(2) 0.0344(13) Uani 1 1 d . . . . .
C18 C 0.6757(3) 1.0934(3) 0.1609(3) 0.0374(13) Uani 1 1 d . . . . .
H18A H 0.6209 1.0883 0.1704 0.056 Uiso 1 1 calc GR . . . .
H18B H 0.6636 1.1136 0.1164 0.056 Uiso 1 1 calc GR . . . .
H18C H 0.7142 1.1338 0.1910 0.056 Uiso 1 1 calc GR . . . .
C19 C 0.5860(3) 0.9095(4) 0.1636(3) 0.0425(15) Uani 1 1 d . . . . .
H19A H 0.5827 0.8572 0.1870 0.064 Uiso 1 1 calc GR . . . .
H19B H 0.5499 0.9036 0.1181 0.064 Uiso 1 1 calc GR . . . .
H19C H 0.5648 0.9574 0.1830 0.064 Uiso 1 1 calc GR . . . .
C20 C 0.7318(4) 0.7678(3) 0.1685(3) 0.0420(15) Uani 1 1 d . . . . .
H20A H 0.7829 0.7414 0.1998 0.063 Uiso 1 1 calc GR . . . .
H20B H 0.7251 0.7466 0.1250 0.063 Uiso 1 1 calc GR . . . .
H20C H 0.6796 0.7537 0.1796 0.063 Uiso 1 1 calc GR . . . .
C21 C 0.9043(4) 0.8641(3) 0.1671(3) 0.0385(14) Uani 1 1 d . . . . .
H21A H 0.9546 0.9006 0.1878 0.058 Uiso 1 1 calc GR . . . .
H21B H 0.8987 0.8562 0.1214 0.058 Uiso 1 1 calc GR . . . .
H21C H 0.9127 0.8088 0.1888 0.058 Uiso 1 1 calc GR . . . .
C22 C 0.8694(4) 1.0625(3) 0.1678(3) 0.0442(15) Uani 1 1 d . . . . .
H22A H 0.8648 1.1089 0.1964 0.066 Uiso 1 1 calc GR . . . .
H22B H 0.8558 1.0840 0.1235 0.066 Uiso 1 1 calc GR . . . .
H22C H 0.9289 1.0398 0.1827 0.066 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.5000 1.17860(11) 0.2500 0.0295(4) Uani 1 2 d S T P . .
Cl3 Cl 0.64563(11) 0.64937(12) 0.41215(9) 0.0634(5) Uani 1 1 d . . . . .
Ir1' Ir 0.77337(2) 0.38025(2) 0.23097(2) 0.02536(6) Uani 1 1 d . . . . .
Cl1' Cl 0.84389(8) 0.29166(8) 0.17394(6) 0.0323(3) Uani 1 1 d . . . . .
F1' F 0.4720(2) 0.2288(2) -0.04572(16) 0.0499(9) Uani 1 1 d . . . . .
F2' F 0.3796(2) 0.2457(2) 0.00368(17) 0.0549(10) Uani 1 1 d . . . . .
F3' F 0.4109(2) 0.3497(2) -0.04808(17) 0.0513(10) Uani 1 1 d . . . . .
F4' F 0.7027(2) 0.6191(2) -0.05022(16) 0.0512(9) Uani 1 1 d . . . . .
F5' F 0.8105(2) 0.6909(2) 0.01134(16) 0.0489(9) Uani 1 1 d . . . . .
F6' F 0.8329(2) 0.5753(2) -0.03323(18) 0.0564(10) Uani 1 1 d . . . . .
N1' N 0.6587(2) 0.3508(2) 0.1561(2) 0.0247(9) Uani 1 1 d . . . . .
N2' N 0.7730(2) 0.4675(3) 0.1581(2) 0.0260(9) Uani 1 1 d . . . . .
C1' C 0.5995(3) 0.2940(3) 0.1605(3) 0.0289(12) Uani 1 1 d . . . . .
H1' H 0.6071 0.2678 0.2011 0.035 Uiso 1 1 calc R . . . .
C2' C 0.5281(3) 0.2720(3) 0.1085(3) 0.0311(12) Uani 1 1 d . . . . .
H2' H 0.4871 0.2315 0.1131 0.037 Uiso 1 1 calc R . . . .
C3' C 0.5175(3) 0.3099(3) 0.0500(3) 0.0317(12) Uani 1 1 d . . . . .
C4' C 0.5768(3) 0.3702(3) 0.0439(3) 0.0322(12) Uani 1 1 d . . . . .
H4' H 0.5697 0.3968 0.0035 0.039 Uiso 1 1 calc R . . . .
C5' C 0.6473(3) 0.3905(3) 0.0990(3) 0.0276(12) Uani 1 1 d . . . . .
C6' C 0.7126(3) 0.4543(3) 0.0990(2) 0.0268(11) Uani 1 1 d . . . . .
C7' C 0.7149(3) 0.5002(3) 0.0456(3) 0.0324(12) Uani 1 1 d . . . . .
H7' H 0.6739 0.4890 0.0041 0.039 Uiso 1 1 calc R . . . .
C8' C 0.7775(3) 0.5624(3) 0.0533(3) 0.0291(12) Uani 1 1 d . . . . .
C9' C 0.8367(3) 0.5774(3) 0.1133(3) 0.0297(12) Uani 1 1 d . . . . .
H9' H 0.8789 0.6212 0.1196 0.036 Uiso 1 1 calc R . . . .
C10' C 0.8336(3) 0.5274(3) 0.1647(3) 0.0284(12) Uani 1 1 d . . . . .
H10' H 0.8761 0.5359 0.2060 0.034 Uiso 1 1 calc R . . . .
C11' C 0.4447(3) 0.2843(4) -0.0100(3) 0.0378(14) Uani 1 1 d . . . . .
C12' C 0.7812(4) 0.6121(4) -0.0048(3) 0.0400(14) Uani 1 1 d . . . . .
C13' C 0.7648(3) 0.3202(3) 0.3179(2) 0.0285(12) Uani 1 1 d . . . . .
C14' C 0.7195(3) 0.4008(3) 0.3082(2) 0.0319(12) Uani 1 1 d . . . . .
C15' C 0.7825(3) 0.4662(3) 0.3096(2) 0.0304(12) Uani 1 1 d . . . . .
C16' C 0.8669(3) 0.4255(3) 0.3208(2) 0.0310(12) Uani 1 1 d . . . . .
C17' C 0.8545(3) 0.3359(3) 0.3264(2) 0.0302(12) Uani 1 1 d . . . . .
C18' C 0.7296(3) 0.2350(3) 0.3284(3) 0.0372(14) Uani 1 1 d . . . . .
H18D H 0.7592 0.1901 0.3124 0.056 Uiso 1 1 calc GR . . . .
H18E H 0.6669 0.2327 0.3049 0.056 Uiso 1 1 calc GR . . . .
H18F H 0.7397 0.2265 0.3747 0.056 Uiso 1 1 calc GR . . . .
C19' C 0.6250(3) 0.4151(4) 0.2992(3) 0.0392(14) Uani 1 1 d . . . . .
H19D H 0.5943 0.3605 0.2918 0.059 Uiso 1 1 calc GR . . . .
H19E H 0.5996 0.4524 0.2619 0.059 Uiso 1 1 calc GR . . . .
H19F H 0.6193 0.4419 0.3382 0.059 Uiso 1 1 calc GR . . . .
C20' C 0.7634(4) 0.5592(3) 0.3022(3) 0.0374(14) Uani 1 1 d . . . . .
H20D H 0.7086 0.5684 0.2668 0.056 Uiso 1 1 calc GR . . . .
H20E H 0.8109 0.5884 0.2922 0.056 Uiso 1 1 calc GR . . . .
H20F H 0.7582 0.5818 0.3425 0.056 Uiso 1 1 calc GR . . . .
C21' C 0.9536(3) 0.4671(3) 0.3324(3) 0.0348(13) Uani 1 1 d . . . . .
H21D H 0.9452 0.5233 0.3119 0.052 Uiso 1 1 calc GR . . . .
H21E H 0.9894 0.4320 0.3138 0.052 Uiso 1 1 calc GR . . . .
H21F H 0.9831 0.4733 0.3790 0.052 Uiso 1 1 calc GR . . . .
C22' C 0.9238(3) 0.2698(3) 0.3382(3) 0.0382(14) Uani 1 1 d . . . . .
H22D H 0.9704 0.2903 0.3227 0.057 Uiso 1 1 calc GR . . . .
H22E H 0.8988 0.2176 0.3151 0.057 Uiso 1 1 calc GR . . . .
H22F H 0.9476 0.2580 0.3847 0.057 Uiso 1 1 calc GR . . . .
Cl2' Cl 1.0000 0.65873(10) 0.2500 0.0263(4) Uani 1 2 d S T P . .
O1S O 0.7206(3) 0.7815(2) 0.5314(2) 0.0421(10) Uani 1 1 d D . . . .
H1SA H 0.754(3) 0.759(3) 0.5714(14) 0.063 Uiso 1 1 d DR . . . .
H1SB H 0.705(4) 0.736(2) 0.503(2) 0.063 Uiso 1 1 d DR . . . .


_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 2.3832(13) . ?
Ir1 N1 2.082(4) . ?
Ir1 N2 2.092(4) . ?
Ir1 C13 2.168(5) . ?
Ir1 C14 2.156(5) . ?
Ir1 C15 2.161(5) . ?
Ir1 C16 2.170(5) . ?
Ir1 C17 2.203(5) . ?
F1 C11 1.333(7) . ?
F2 C11 1.339(6) . ?
F3 C11 1.326(7) . ?
F4 C12 1.302(7) . ?
F5 C12 1.312(7) . ?
F6 C12 1.328(7) . ?
N1 C1 1.345(6) . ?
N1 C5 1.365(6) . ?
N2 C6 1.353(6) . ?
N2 C10 1.356(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(7) . ?
C3 C4 1.389(7) . ?
C3 C11 1.511(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(7) . ?
C5 C6 1.466(7) . ?
C6 C7 1.395(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(7) . ?
C8 C9 1.386(7) . ?
C8 C12 1.496(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.367(7) . ?
C10 H10 0.9500 . ?
C13 C14 1.445(7) . ?
C13 C17 1.426(7) . ?
C13 C18 1.509(7) . ?
C14 C15 1.433(7) . ?
C14 C19 1.513(7) . ?
C15 C16 1.457(8) . ?
C15 C20 1.484(7) . ?
C16 C17 1.425(7) . ?
C16 C21 1.496(7) . ?
C17 C22 1.487(8) . ?
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 . ?
Ir1' Cl1' 2.3946(13) . ?
Ir1' N1' 2.091(4) . ?
Ir1' N2' 2.101(4) . ?
Ir1' C13' 2.167(5) . ?
Ir1' C14' 2.162(5) . ?
Ir1' C15' 2.154(5) . ?
Ir1' C16' 2.173(5) . ?
Ir1' C17' 2.186(5) . ?
F1' C11' 1.340(6) . ?
F2' C11' 1.335(6) . ?
F3' C11' 1.326(6) . ?
F4' C12' 1.341(6) . ?
F5' C12' 1.334(6) . ?
F6' C12' 1.329(7) . ?
N1' C1' 1.338(6) . ?
N1' C5' 1.354(6) . ?
N2' C6' 1.359(6) . ?
N2' C10' 1.336(6) . ?
C1' H1' 0.9500 . ?
C1' C2' 1.377(7) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.369(7) . ?
C3' C4' 1.388(7) . ?
C3' C11' 1.506(7) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.402(7) . ?
C5' C6' 1.460(7) . ?
C6' C7' 1.383(7) . ?
C7' H7' 0.9500 . ?
C7' C8' 1.381(7) . ?
C8' C9' 1.371(7) . ?
C8' C12' 1.508(8) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.385(7) . ?
C10' H10' 0.9500 . ?
C13' C14' 1.446(7) . ?
C13' C17' 1.427(7) . ?
C13' C18' 1.505(7) . ?
C14' C15' 1.443(7) . ?
C14' C19' 1.498(7) . ?
C15' C16' 1.459(7) . ?
C15' C20' 1.494(7) . ?
C16' C17' 1.435(7) . ?
C16' C21' 1.497(7) . ?
C17' C22' 1.491(7) . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 0.9800 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
C21' H21D 0.9800 . ?
C21' H21E 0.9800 . ?
C21' H21F 0.9800 . ?
C22' H22D 0.9800 . ?
C22' H22E 0.9800 . ?
C22' H22F 0.9800 . ?
O1S H1SA 0.935(19) . ?
O1S H1SB 0.931(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 Cl1 84.27(11) . . ?
N1 Ir1 N2 76.38(16) . . ?
N1 Ir1 C13 106.68(17) . . ?
N1 Ir1 C14 99.74(18) . . ?
N1 Ir1 C15 125.87(19) . . ?
N1 Ir1 C16 164.27(18) . . ?
N1 Ir1 C17 140.66(18) . . ?
N2 Ir1 Cl1 85.16(11) . . ?
N2 Ir1 C13 163.85(18) . . ?
N2 Ir1 C14 125.15(18) . . ?
N2 Ir1 C15 99.89(19) . . ?
N2 Ir1 C16 108.37(17) . . ?
N2 Ir1 C17 142.73(18) . . ?
C13 Ir1 Cl1 110.81(15) . . ?
C13 Ir1 C16 64.58(18) . . ?
C13 Ir1 C17 38.08(18) . . ?
C14 Ir1 Cl1 149.61(15) . . ?
C14 Ir1 C13 39.1(2) . . ?
C14 Ir1 C15 38.76(19) . . ?
C14 Ir1 C16 65.1(2) . . ?
C14 Ir1 C17 64.3(2) . . ?
C15 Ir1 Cl1 149.85(16) . . ?
C15 Ir1 C13 65.2(2) . . ?
C15 Ir1 C16 39.3(2) . . ?
C15 Ir1 C17 64.5(2) . . ?
C16 Ir1 Cl1 110.81(15) . . ?
C16 Ir1 C17 38.02(19) . . ?
C17 Ir1 Cl1 93.53(15) . . ?
C1 N1 Ir1 124.2(3) . . ?
C1 N1 C5 117.9(4) . . ?
C5 N1 Ir1 117.6(3) . . ?
C6 N2 Ir1 117.4(3) . . ?
C6 N2 C10 118.6(4) . . ?
C10 N2 Ir1 124.0(3) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.0(5) . . ?
C2 C1 H1 118.5 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.5(5) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.3(5) . . ?
C2 C3 C11 121.0(5) . . ?
C4 C3 C11 118.6(5) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.1(5) . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 122.0(5) . . ?
N1 C5 C6 113.9(4) . . ?
C4 C5 C6 124.1(5) . . ?
N2 C6 C5 114.5(4) . . ?
N2 C6 C7 121.9(5) . . ?
C7 C6 C5 123.6(5) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.7(5) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C9 118.9(5) . . ?
C7 C8 C12 120.6(5) . . ?
C9 C8 C12 120.4(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(5) . . ?
C10 C9 H9 120.0 . . ?
N2 C10 C9 121.9(5) . . ?
N2 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
F1 C11 F2 106.8(5) . . ?
F1 C11 C3 111.1(5) . . ?
F2 C11 C3 111.5(5) . . ?
F3 C11 F1 107.4(5) . . ?
F3 C11 F2 107.4(5) . . ?
F3 C11 C3 112.3(5) . . ?
F4 C12 F5 108.4(5) . . ?
F4 C12 F6 105.6(5) . . ?
F4 C12 C8 114.5(5) . . ?
F5 C12 F6 104.9(5) . . ?
F5 C12 C8 111.9(5) . . ?
F6 C12 C8 110.9(5) . . ?
C14 C13 Ir1 70.0(3) . . ?
C14 C13 C18 127.2(5) . . ?
C17 C13 Ir1 72.3(3) . . ?
C17 C13 C14 107.8(4) . . ?
C17 C13 C18 124.6(5) . . ?
C18 C13 Ir1 129.0(4) . . ?
C13 C14 Ir1 70.9(3) . . ?
C13 C14 C19 126.0(5) . . ?
C15 C14 Ir1 70.8(3) . . ?
C15 C14 C13 108.3(5) . . ?
C15 C14 C19 125.8(5) . . ?
C19 C14 Ir1 125.2(4) . . ?
C14 C15 Ir1 70.4(3) . . ?
C14 C15 C16 107.2(5) . . ?
C14 C15 C20 127.8(5) . . ?
C16 C15 Ir1 70.7(3) . . ?
C16 C15 C20 125.0(5) . . ?
C20 C15 Ir1 125.6(4) . . ?
C15 C16 Ir1 70.0(3) . . ?
C15 C16 C21 126.2(5) . . ?
C17 C16 Ir1 72.2(3) . . ?
C17 C16 C15 107.9(4) . . ?
C17 C16 C21 125.3(5) . . ?
C21 C16 Ir1 130.4(4) . . ?
C13 C17 Ir1 69.6(3) . . ?
C13 C17 C22 124.9(5) . . ?
C16 C17 Ir1 69.7(3) . . ?
C16 C17 C13 108.8(5) . . ?
C16 C17 C22 126.4(5) . . ?
C22 C17 Ir1 126.3(4) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1' Ir1' Cl1' 85.31(11) . . ?
N1' Ir1' N2' 76.66(16) . . ?
N1' Ir1' C13' 107.16(17) . . ?
N1' Ir1' C14' 99.25(18) . . ?
N1' Ir1' C15' 125.15(17) . . ?
N1' Ir1' C16' 163.97(18) . . ?
N1' Ir1' C17' 141.41(17) . . ?
N2' Ir1' Cl1' 82.54(11) . . ?
N2' Ir1' C13' 164.65(18) . . ?
N2' Ir1' C14' 126.24(18) . . ?
N2' Ir1' C15' 100.20(18) . . ?
N2' Ir1' C16' 107.42(17) . . ?
N2' Ir1' C17' 141.61(17) . . ?
C13' Ir1' Cl1' 112.37(15) . . ?
C13' Ir1' C16' 64.90(18) . . ?
C13' Ir1' C17' 38.27(18) . . ?
C14' Ir1' Cl1' 151.19(15) . . ?
C14' Ir1' C13' 39.04(19) . . ?
C14' Ir1' C16' 65.6(2) . . ?
C14' Ir1' C17' 64.8(2) . . ?
C15' Ir1' Cl1' 149.38(14) . . ?
C15' Ir1' C13' 65.2(2) . . ?
C15' Ir1' C14' 39.1(2) . . ?
C15' Ir1' C16' 39.40(19) . . ?
C15' Ir1' C17' 64.9(2) . . ?
C16' Ir1' Cl1' 110.45(15) . . ?
C16' Ir1' C17' 38.43(19) . . ?
C17' Ir1' Cl1' 93.97(15) . . ?
C1' N1' Ir1' 124.7(3) . . ?
C1' N1' C5' 119.2(4) . . ?
C5' N1' Ir1' 116.0(3) . . ?
C6' N2' Ir1' 116.4(3) . . ?
C10' N2' Ir1' 124.0(3) . . ?
C10' N2' C6' 119.2(4) . . ?
N1' C1' H1' 118.7 . . ?
N1' C1' C2' 122.7(5) . . ?
C2' C1' H1' 118.7 . . ?
C1' C2' H2' 120.8 . . ?
C3' C2' C1' 118.4(5) . . ?
C3' C2' H2' 120.8 . . ?
C2' C3' C4' 120.6(5) . . ?
C2' C3' C11' 121.3(5) . . ?
C4' C3' C11' 118.0(5) . . ?
C3' C4' H4' 121.0 . . ?
C3' C4' C5' 118.0(5) . . ?
C5' C4' H4' 121.0 . . ?
N1' C5' C4' 121.0(5) . . ?
N1' C5' C6' 115.9(4) . . ?
C4' C5' C6' 123.2(5) . . ?
N2' C6' C5' 113.8(5) . . ?
N2' C6' C7' 120.9(4) . . ?
C7' C6' C5' 125.3(5) . . ?
C6' C7' H7' 120.4 . . ?
C8' C7' C6' 119.2(5) . . ?
C8' C7' H7' 120.4 . . ?
C7' C8' C12' 119.6(5) . . ?
C9' C8' C7' 119.8(5) . . ?
C9' C8' C12' 120.6(5) . . ?
C8' C9' H9' 120.7 . . ?
C8' C9' C10' 118.6(5) . . ?
C10' C9' H9' 120.7 . . ?
N2' C10' C9' 122.2(5) . . ?
N2' C10' H10' 118.9 . . ?
C9' C10' H10' 118.9 . . ?
F1' C11' C3' 111.6(4) . . ?
F2' C11' F1' 105.7(4) . . ?
F2' C11' C3' 112.4(5) . . ?
F3' C11' F1' 106.7(5) . . ?
F3' C11' F2' 107.3(4) . . ?
F3' C11' C3' 112.7(5) . . ?
F4' C12' C8' 112.1(5) . . ?
F5' C12' F4' 106.9(5) . . ?
F5' C12' C8' 111.6(5) . . ?
F6' C12' F4' 106.4(5) . . ?
F6' C12' F5' 107.7(5) . . ?
F6' C12' C8' 111.8(5) . . ?
C14' C13' Ir1' 70.3(3) . . ?
C14' C13' C18' 127.2(5) . . ?
C17' C13' Ir1' 71.6(3) . . ?
C17' C13' C14' 108.4(4) . . ?
C17' C13' C18' 123.8(5) . . ?
C18' C13' Ir1' 131.1(4) . . ?
C13' C14' Ir1' 70.6(3) . . ?
C13' C14' C19' 126.9(5) . . ?
C15' C14' Ir1' 70.2(3) . . ?
C15' C14' C13' 107.4(4) . . ?
C15' C14' C19' 125.7(5) . . ?
C19' C14' Ir1' 125.2(4) . . ?
C14' C15' Ir1' 70.8(3) . . ?
C14' C15' C16' 108.1(4) . . ?
C14' C15' C20' 125.2(5) . . ?
C16' C15' Ir1' 71.0(3) . . ?
C16' C15' C20' 126.7(5) . . ?
C20' C15' Ir1' 124.7(4) . . ?
C15' C16' Ir1' 69.6(3) . . ?
C15' C16' C21' 128.0(5) . . ?
C17' C16' Ir1' 71.3(3) . . ?
C17' C16' C15' 107.2(4) . . ?
C17' C16' C21' 124.5(5) . . ?
C21' C16' Ir1' 129.6(4) . . ?
C13' C17' Ir1' 70.1(3) . . ?
C13' C17' C16' 108.9(5) . . ?
C13' C17' C22' 125.5(5) . . ?
C16' C17' Ir1' 70.3(3) . . ?
C16' C17' C22' 125.6(5) . . ?
C22' C17' Ir1' 125.0(4) . . ?
C13' C18' H18D 109.5 . . ?
C13' C18' H18E 109.5 . . ?
C13' C18' H18F 109.5 . . ?
H18D C18' H18E 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C14' C19' H19D 109.5 . . ?
C14' C19' H19E 109.5 . . ?
C14' C19' H19F 109.5 . . ?
H19D C19' H19E 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C15' C20' H20D 109.5 . . ?
C15' C20' H20E 109.5 . . ?
C15' C20' H20F 109.5 . . ?
H20D C20' H20E 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C16' C21' H21D 109.5 . . ?
C16' C21' H21E 109.5 . . ?
C16' C21' H21F 109.5 . . ?
H21D C21' H21E 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C17' C22' H22D 109.5 . . ?
C17' C22' H22E 109.5 . . ?
C17' C22' H22F 109.5 . . ?
H22D C22' H22E 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
H1SA O1S H1SB 106(3) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
