# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_gh9
_database_code_depnum_ccdc_archive 'CCDC 1860992'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2018-08-08 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2017-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 I Ir N3 O, I, C H4 O'
_chemical_formula_sum            'C22 H28 I2 Ir N3 O2'
_chemical_formula_weight         812.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 I Ir'
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'
I I -0.4742 1.8119 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.29339(12)
_cell_length_b                   13.27724(15)
_cell_length_c                   20.1881(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.3644(12)
_cell_angle_gamma                90
_cell_volume                     2490.31(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28091
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.6600
_cell_measurement_theta_min      3.2170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            64660
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.131
_diffrn_reflns_theta_min         2.435
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  27.00   1.00    5.00    --  -14.18 -99.00-150.00   47
  2  ω     -9.00  90.00   1.00    5.00    --   15.28  37.00-180.00   99
  3  ω    -13.00  88.00   1.00    5.00    --   15.28  57.00  30.00  101
  4  ω    -17.00  91.00   1.00    5.00    --   15.28  77.00 150.00  108
  5  ω    -58.00  43.00   1.00    5.00    --   15.28 -57.00-120.00  101
  6  ω   -101.00 -55.00   1.00    5.00    --  -14.18 178.00-150.00   46
  7  ω    -13.00  88.00   1.00    5.00    --   15.28  57.00 -90.00  101
  8  ω     35.00 104.00   1.00    5.00    --   15.28 178.00-120.00   69
  9  ω    -61.00  48.00   1.00    5.00    --   15.28 -77.00 150.00  109
 10  ω    -20.00  56.00   1.00    5.00    --   15.28 -99.00  60.00   76
 11  ω    -20.00  35.00   1.00    5.00    --   15.28 -99.00   0.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0235945000
_diffrn_orient_matrix_UB_12      0.0377248000
_diffrn_orient_matrix_UB_13      -0.0226451000
_diffrn_orient_matrix_UB_21      0.0725742000
_diffrn_orient_matrix_UB_22      0.0132049000
_diffrn_orient_matrix_UB_23      -0.0057837000
_diffrn_orient_matrix_UB_31      0.0019320000
_diffrn_orient_matrix_UB_32      -0.0354534000
_diffrn_orient_matrix_UB_33      -0.0262467000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6650
_reflns_number_total             7479
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.02
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.569
_refine_diff_density_min         -0.898
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         7479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0208
_refine_ls_restrained_S_all      1.093
_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)+(0.0125P)²+1.1630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0381
_refine_ls_wR_factor_ref         0.0398
_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) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
2.c Idealised tetrahedral OH refined as rotating group:
 O12(H12), O25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.59618(2) 0.25513(2) 0.33910(2) 0.01405(3) Uani 1 1 d . . . . .
N1 N 0.6310(2) 0.33918(14) 0.42493(9) 0.0176(4) Uani 1 1 d . . . . .
C2 C 0.5555(3) 0.33661(18) 0.48066(12) 0.0240(5) Uani 1 1 d . . . . .
H2 H 0.4759 0.2921 0.4835 0.029 Uiso 1 1 calc R . . . .
I1 I 0.41423(2) 0.40335(2) 0.30308(2) 0.01839(4) Uani 1 1 d . . . . .
C3 C 0.5916(3) 0.39809(19) 0.53449(13) 0.0288(6) Uani 1 1 d . . . . .
H3 H 0.5389 0.3934 0.5741 0.035 Uiso 1 1 calc R . . . .
C4 C 0.7035(3) 0.4657(2) 0.53033(13) 0.0308(6) Uani 1 1 d . . . . .
H4 H 0.7278 0.5084 0.5667 0.037 Uiso 1 1 calc R . . . .
C5 C 0.7797(3) 0.47061(19) 0.47252(13) 0.0269(6) Uani 1 1 d . . . . .
H5 H 0.8566 0.5170 0.4680 0.032 Uiso 1 1 calc R . . . .
C6 C 0.7409(3) 0.40595(17) 0.42120(12) 0.0202(5) Uani 1 1 d . . . . .
N7 N 0.8153(2) 0.40976(14) 0.36261(10) 0.0203(4) Uani 1 1 d . . . . .
N8 N 0.76494(19) 0.34849(13) 0.31887(9) 0.0158(4) Uani 1 1 d . . . . .
C9 C 0.8436(2) 0.34747(16) 0.25901(11) 0.0163(4) Uani 1 1 d . . . . .
C10 C 0.9924(2) 0.35863(17) 0.26095(12) 0.0191(5) Uani 1 1 d . . . . .
H10 H 1.0422 0.3698 0.3019 0.023 Uiso 1 1 calc R . . . .
C11 C 1.0671(2) 0.35327(17) 0.20284(12) 0.0201(5) Uani 1 1 d . . . . .
H11 H 1.1689 0.3600 0.2039 0.024 Uiso 1 1 calc R . . . .
C12 C 0.9938(2) 0.33803(17) 0.14232(12) 0.0188(5) Uani 1 1 d . . . . .
O12 O 1.06296(18) 0.33185(14) 0.08459(8) 0.0252(4) Uani 1 1 d . . . . .
H12 H 1.1522 0.3315 0.0921 0.038 Uiso 1 1 calc GR . . . .
C13 C 0.8445(3) 0.32779(17) 0.14066(12) 0.0206(5) Uani 1 1 d . . . . .
H13 H 0.7944 0.3178 0.0996 0.025 Uiso 1 1 calc R . . . .
C14 C 0.7696(2) 0.33223(17) 0.19899(12) 0.0187(5) Uani 1 1 d . . . . .
H14 H 0.6679 0.3249 0.1981 0.022 Uiso 1 1 calc R . . . .
C15 C 0.4397(3) 0.13478(16) 0.31140(12) 0.0199(5) Uani 1 1 d . . . . .
C16 C 0.5574(3) 0.13630(16) 0.26510(12) 0.0220(5) Uani 1 1 d . . . . .
C17 C 0.6872(3) 0.11469(16) 0.30262(12) 0.0214(5) Uani 1 1 d . . . . .
C18 C 0.6516(2) 0.10412(16) 0.37115(12) 0.0178(5) Uani 1 1 d . . . . .
C19 C 0.4970(2) 0.11516(16) 0.37563(12) 0.0179(5) Uani 1 1 d . . . . .
C20 C 0.4119(3) 0.09781(18) 0.43677(13) 0.0245(5) Uani 1 1 d . . . . .
H20A H 0.4705 0.1159 0.4760 0.037 Uiso 1 1 calc GR . . . .
H20B H 0.3846 0.0266 0.4393 0.037 Uiso 1 1 calc GR . . . .
H20C H 0.3249 0.1395 0.4350 0.037 Uiso 1 1 calc GR . . . .
C21 C 0.7508(3) 0.07768(19) 0.42765(13) 0.0256(5) Uani 1 1 d . . . . .
H21A H 0.8490 0.0984 0.4173 0.038 Uiso 1 1 calc GR . . . .
H21B H 0.7485 0.0047 0.4350 0.038 Uiso 1 1 calc GR . . . .
H21C H 0.7202 0.1125 0.4677 0.038 Uiso 1 1 calc GR . . . .
C22 C 0.8347(3) 0.10182(19) 0.27591(14) 0.0310(6) Uani 1 1 d . . . . .
H22A H 0.8400 0.1357 0.2329 0.046 Uiso 1 1 calc GR . . . .
H22B H 0.8551 0.0299 0.2705 0.046 Uiso 1 1 calc GR . . . .
H22C H 0.9056 0.1314 0.3069 0.046 Uiso 1 1 calc GR . . . .
C23 C 0.5360(3) 0.1399(2) 0.19129(12) 0.0333(6) Uani 1 1 d . . . . .
H23A H 0.4743 0.1972 0.1793 0.050 Uiso 1 1 calc GR . . . .
H23B H 0.4904 0.0773 0.1760 0.050 Uiso 1 1 calc GR . . . .
H23C H 0.6295 0.1475 0.1704 0.050 Uiso 1 1 calc GR . . . .
C24 C 0.2840(3) 0.14502(19) 0.29278(14) 0.0290(6) Uani 1 1 d . . . . .
H24A H 0.2326 0.1751 0.3297 0.044 Uiso 1 1 calc GR . . . .
H24B H 0.2437 0.0784 0.2828 0.044 Uiso 1 1 calc GR . . . .
H24C H 0.2736 0.1883 0.2536 0.044 Uiso 1 1 calc GR . . . .
I2 I 0.07474(2) 0.26663(2) 0.47489(2) 0.03150(5) Uani 1 1 d . . . . .
O25 O 0.84724(19) 0.16859(15) 0.59135(10) 0.0338(5) Uani 1 1 d . . . . .
H25 H 0.8890 0.2047 0.5636 0.051 Uiso 1 1 calc GR . . . .
C26 C 0.9202(3) 0.0746(2) 0.59771(14) 0.0353(6) Uani 1 1 d . . . . .
H26A H 0.9137 0.0383 0.5555 0.053 Uiso 1 1 calc GR . . . .
H26B H 0.8754 0.0343 0.6323 0.053 Uiso 1 1 calc GR . . . .
H26C H 1.0215 0.0865 0.6097 0.053 Uiso 1 1 calc GR . . . .


_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 N1 2.0799(19) . ?
Ir1 I1 2.68371(16) . ?
Ir1 N8 2.0479(18) . ?
Ir1 C15 2.223(2) . ?
Ir1 C16 2.197(2) . ?
Ir1 C17 2.183(2) . ?
Ir1 C18 2.165(2) . ?
Ir1 C19 2.209(2) . ?
N1 C2 1.341(3) . ?
N1 C6 1.356(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 N7 1.385(3) . ?
N7 N8 1.281(3) . ?
N8 C9 1.427(3) . ?
C9 C10 1.391(3) . ?
C9 C14 1.393(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.399(3) . ?
C12 O12 1.346(3) . ?
C12 C13 1.394(3) . ?
O12 H12 0.8400 . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.456(3) . ?
C15 C19 1.414(3) . ?
C15 C24 1.492(3) . ?
C16 C17 1.438(3) . ?
C16 C23 1.499(3) . ?
C17 C18 1.437(3) . ?
C17 C22 1.494(3) . ?
C18 C19 1.449(3) . ?
C18 C21 1.492(3) . ?
C19 C20 1.500(3) . ?
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 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O25 H25 0.8400 . ?
O25 C26 1.425(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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 I1 85.23(5) . . ?
N1 Ir1 C15 133.10(8) . . ?
N1 Ir1 C16 166.34(8) . . ?
N1 Ir1 C17 133.28(8) . . ?
N1 Ir1 C18 102.51(8) . . ?
N1 Ir1 C19 103.37(8) . . ?
N8 Ir1 N1 74.72(7) . . ?
N8 Ir1 I1 89.01(5) . . ?
N8 Ir1 C15 152.18(8) . . ?
N8 Ir1 C16 114.40(8) . . ?
N8 Ir1 C17 98.34(8) . . ?
N8 Ir1 C18 116.25(8) . . ?
N8 Ir1 C19 154.62(8) . . ?
C15 Ir1 I1 93.14(6) . . ?
C16 Ir1 I1 104.50(6) . . ?
C16 Ir1 C15 38.46(9) . . ?
C16 Ir1 C19 63.89(9) . . ?
C17 Ir1 I1 141.42(7) . . ?
C17 Ir1 C15 63.73(9) . . ?
C17 Ir1 C16 38.33(9) . . ?
C17 Ir1 C19 64.03(9) . . ?
C18 Ir1 I1 154.67(6) . . ?
C18 Ir1 C15 63.83(8) . . ?
C18 Ir1 C16 64.67(9) . . ?
C18 Ir1 C17 38.60(9) . . ?
C18 Ir1 C19 38.67(8) . . ?
C19 Ir1 I1 116.24(6) . . ?
C19 Ir1 C15 37.21(8) . . ?
C2 N1 Ir1 127.67(16) . . ?
C2 N1 C6 118.3(2) . . ?
C6 N1 Ir1 114.03(15) . . ?
N1 C2 H2 119.4 . . ?
N1 C2 C3 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 123.1(2) . . ?
N1 C6 N7 117.6(2) . . ?
N7 C6 C5 119.3(2) . . ?
N8 N7 C6 112.58(19) . . ?
N7 N8 Ir1 121.05(15) . . ?
N7 N8 C9 113.82(18) . . ?
C9 N8 Ir1 124.97(14) . . ?
C10 C9 N8 120.3(2) . . ?
C10 C9 C14 120.6(2) . . ?
C14 C9 N8 119.06(19) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
O12 C12 C11 122.2(2) . . ?
O12 C12 C13 117.9(2) . . ?
C13 C12 C11 119.9(2) . . ?
C12 O12 H12 109.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.9(2) . . ?
C13 C14 H14 120.0 . . ?
C16 C15 Ir1 69.78(13) . . ?
C16 C15 C24 125.2(2) . . ?
C19 C15 Ir1 70.85(13) . . ?
C19 C15 C16 108.6(2) . . ?
C19 C15 C24 126.1(2) . . ?
C24 C15 Ir1 128.49(16) . . ?
C15 C16 Ir1 71.76(13) . . ?
C15 C16 C23 123.7(2) . . ?
C17 C16 Ir1 70.32(13) . . ?
C17 C16 C15 107.0(2) . . ?
C17 C16 C23 128.3(2) . . ?
C23 C16 Ir1 131.97(17) . . ?
C16 C17 Ir1 71.36(13) . . ?
C16 C17 C22 126.7(2) . . ?
C18 C17 Ir1 70.04(12) . . ?
C18 C17 C16 108.5(2) . . ?
C18 C17 C22 124.8(2) . . ?
C22 C17 Ir1 125.83(17) . . ?
C17 C18 Ir1 71.36(12) . . ?
C17 C18 C19 107.6(2) . . ?
C17 C18 C21 127.4(2) . . ?
C19 C18 Ir1 72.30(12) . . ?
C19 C18 C21 124.9(2) . . ?
C21 C18 Ir1 125.79(16) . . ?
C15 C19 Ir1 71.93(13) . . ?
C15 C19 C18 108.3(2) . . ?
C15 C19 C20 126.1(2) . . ?
C18 C19 Ir1 69.02(12) . . ?
C18 C19 C20 125.4(2) . . ?
C20 C19 Ir1 129.53(16) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 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 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 O25 H25 109.5 . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
O12 H12 O25 0.84 1.81 2.642(2) 169.1 4_665
O25 H25 I2 0.84 2.65 3.4537(18) 161.5 1_655

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.708
_oxdiff_exptl_absorpt_empirical_full_min 0.692
####################################################################### 
# 
# 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_wz1
_database_code_depnum_ccdc_archive 'CCDC 1860993'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2018-08-08 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2017-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H25.5 I Ir N3 O, F3 P0.5'
_chemical_formula_sum            'C26 H25.50 F3 I Ir N3 O P0.50'
_chemical_formula_weight         787.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 F6 P Ir'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   23.1650(4)
_cell_length_b                   7.44609(9)
_cell_length_c                   15.7060(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.2675(16)
_cell_angle_gamma                90
_cell_volume                     2587.00(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    34647
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.7940
_cell_measurement_theta_min      2.8820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.022
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1500
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            97034
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.100
_diffrn_reflns_theta_min         2.596
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  48.00   1.00    6.26    --   20.12 -57.00 -60.00  101
  2  ω     -4.00  95.00   1.00    6.26    --   20.12  37.00-180.00   99
  3  ω     34.00 107.00   1.00    6.26    --   20.12-178.00 120.00   73
  4  ω     -8.00  93.00   1.00    6.26    --   20.12  57.00-150.00  101
  5  ω    -56.00  53.00   1.00    6.26    --   20.12 -77.00  90.00  109
  6  ω     -8.00  93.00   1.00    6.26    --   20.12  57.00-120.00  101
  7  ω   -108.00 -57.00   1.00    6.26    --  -19.19-178.00  90.00   51
  8  ω    -12.00  96.00   1.00    6.26    --   20.12  77.00 -60.00  108
  9  ω    -20.00  61.00   1.00    6.26    --   20.12 -99.00-120.00   81
 10  ω     -8.00  93.00   1.00    6.26    --   20.12  57.00  90.00  101
 11  ω     -4.00  95.00   1.00    6.26    --   20.12  37.00  60.00   99
 12  ω    -20.00  61.00   1.00    6.26    --   20.12 -99.00 -30.00   81
 13  ω    -17.00  32.00   1.00    6.26    --   20.12-104.00  72.00   49
 14  ω    -20.00  61.00   1.00    6.26    --   20.12 -99.00-180.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0454527000
_diffrn_orient_matrix_UB_12      -0.0103806000
_diffrn_orient_matrix_UB_13      -0.0169135000
_diffrn_orient_matrix_UB_21      -0.0129325000
_diffrn_orient_matrix_UB_22      0.0234607000
_diffrn_orient_matrix_UB_23      0.0258687000
_diffrn_orient_matrix_UB_31      -0.0018476000
_diffrn_orient_matrix_UB_32      0.0917351000
_diffrn_orient_matrix_UB_33      -0.0085378000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8195
_reflns_number_total             9366
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.805
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         9366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.050
_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)+(0.0119P)²+2.4792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0439
_refine_special_details          ?
_olex2_refinement_description    
;
The PF6 counter ion that sits on a two fold axis. The PF6 is disordered across the two fold axis 
about the meridian of the PF6. F11 is at full occupancy but F12 and F13 were modeled at 75% occupancy. 
The other component of the disorder lies with two of the fluorides (F12A F14A) on the 2 fold axis 
and F13A (at 25% occupancy) on a general position.

This is balanced by the phenol which is partially ionized.
The phenol is partially ionized as two phenoxides share a proton and are related by an inversion centre 
so also contributes half a minus charge. 
The partially occupied proton was located in a difference map but refined at a calculated position at 50% occupancy. 
This works out at one proton (H12) shared between two phenolic oxygens (O12 and a symmetry related O12) related by an 
inversion centre.

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) groups
2. Others
 Fixed Sof: H12(0.5) F12(0.75) F13(0.75) F12A(0.125) F14A(0.125) F13A(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C2(H2), C5(H5), C19(H19), C11(H11), C15(H15), C16(H16),
 C18(H18), C14(H14), C3(H3), C13(H13), C17(H17)
3.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
3.c Idealised tetrahedral OH refined as rotating group:
 O12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.22247(2) 0.39060(2) 0.11163(2) 0.01564(2) Uani 1 1 d . . . . .
I2 I 0.22613(2) 0.12700(2) 0.23027(2) 0.03125(4) Uani 1 1 d . . . . .
C21 C 0.28637(10) 0.5953(3) 0.18669(14) 0.0194(4) Uani 1 1 d . . . . .
C6 C 0.15207(9) 0.1730(3) -0.03458(14) 0.0201(4) Uani 1 1 d . . . . .
C23 C 0.21280(10) 0.6546(3) 0.05145(14) 0.0225(4) Uani 1 1 d . . . . .
C9 C 0.31088(9) 0.1741(3) 0.03750(14) 0.0198(4) Uani 1 1 d . . . . .
C12 C 0.43282(11) 0.1009(3) 0.0553(2) 0.0343(6) Uani 1 1 d . . . . .
C10 C 0.35582(10) 0.2083(3) 0.11835(16) 0.0280(5) Uani 1 1 d . . . . .
H10 H 0.3449 0.2574 0.1672 0.034 Uiso 1 1 calc R . . . .
C4 C 0.04625(11) 0.1169(4) -0.0899(2) 0.0379(6) Uani 1 1 d . . . . .
H4 H 0.0120 0.0697 -0.1337 0.046 Uiso 1 1 calc R . . . .
N1 N 0.14445(8) 0.2687(2) 0.03469(12) 0.0201(4) Uani 1 1 d . . . . .
C20 C 0.34667(10) 0.5853(3) 0.25437(15) 0.0259(5) Uani 1 1 d . . . . .
C2 C 0.08909(10) 0.2783(3) 0.04590(18) 0.0297(5) Uani 1 1 d . . . . .
H2 H 0.0841 0.3372 0.0969 0.036 Uiso 1 1 calc R . . . .
O12 O 0.48986(8) 0.0697(3) 0.06538(17) 0.0491(6) Uani 1 1 d . . . . .
H12 H 0.4936 0.0210 0.0191 0.074 Uiso 0.5 1 calc GR . . . .
C5 C 0.10345(11) 0.0994(3) -0.09982(17) 0.0288(5) Uani 1 1 d . . . . .
H5 H 0.1093 0.0388 -0.1498 0.035 Uiso 1 1 calc R . . . .
C19 C 0.38813(12) 0.7205(4) 0.25434(18) 0.0374(6) Uani 1 1 d . . . . .
H19 H 0.3771 0.8158 0.2124 0.045 Uiso 1 1 calc R . . . .
C11 C 0.41528(11) 0.1713(4) 0.12723(19) 0.0360(6) Uani 1 1 d . . . . .
H11 H 0.4451 0.1935 0.1826 0.043 Uiso 1 1 calc R . . . .
C15 C 0.36325(12) 0.4490(4) 0.31760(17) 0.0349(6) Uani 1 1 d . . . . .
H15 H 0.3350 0.3578 0.3196 0.042 Uiso 1 1 calc R . . . .
C16 C 0.42100(14) 0.4455(5) 0.3779(2) 0.0499(8) Uani 1 1 d . . . . .
H16 H 0.4322 0.3511 0.4203 0.060 Uiso 1 1 calc R . . . .
C18 C 0.44561(13) 0.7168(5) 0.3153(2) 0.0514(9) Uani 1 1 d . . . . .
H18 H 0.4737 0.8097 0.3151 0.062 Uiso 1 1 calc R . . . .
N8 N 0.25089(8) 0.2129(2) 0.03127(11) 0.0174(3) Uani 1 1 d . . . . .
C14 C 0.32769(10) 0.1003(3) -0.03442(15) 0.0232(4) Uani 1 1 d . . . . .
H14 H 0.2976 0.0745 -0.0890 0.028 Uiso 1 1 calc R . . . .
N7 N 0.21069(8) 0.1417(2) -0.03606(12) 0.0201(4) Uani 1 1 d . . . . .
C28 C 0.18335(13) 0.6932(3) -0.04530(15) 0.0329(6) Uani 1 1 d . . . . .
H28A H 0.1988 0.6099 -0.0816 0.049 Uiso 1 1 calc GR . . . .
H28B H 0.1924 0.8169 -0.0585 0.049 Uiso 1 1 calc GR . . . .
H28C H 0.1395 0.6783 -0.0591 0.049 Uiso 1 1 calc GR . . . .
C3 C 0.03961(11) 0.2037(4) -0.0157(2) 0.0391(6) Uani 1 1 d . . . . .
H3 H 0.0008 0.2120 -0.0070 0.047 Uiso 1 1 calc R . . . .
C13 C 0.38714(11) 0.0659(3) -0.02587(18) 0.0300(5) Uani 1 1 d . . . . .
H13 H 0.3980 0.0179 -0.0750 0.036 Uiso 1 1 calc R . . . .
C17 C 0.46194(13) 0.5785(5) 0.3762(2) 0.0575(10) Uani 1 1 d . . . . .
H17 H 0.5015 0.5749 0.4170 0.069 Uiso 1 1 calc R . . . .
P10 P 0.0000 0.37045(14) 0.2500 0.0352(2) Uani 1 2 d S T P . .
F11 F -0.01942(10) 0.3686(3) 0.14384(12) 0.0669(6) Uani 1 1 d . . . . .
F12 F -0.04962(18) 0.5110(6) 0.2490(2) 0.1025(14) Uani 0.75 1 d . . . A 1
F13 F -0.04751(16) 0.2143(5) 0.2505(2) 0.0901(12) Uani 0.75 1 d . . . A 1
C22 C 0.27622(10) 0.6232(3) 0.09274(14) 0.0208(4) Uani 1 1 d . . . . .
C24 C 0.18386(10) 0.6563(3) 0.12146(14) 0.0214(4) Uani 1 1 d . . . . .
C29 C 0.32316(12) 0.6244(3) 0.04486(17) 0.0302(5) Uani 1 1 d . . . . .
H29A H 0.3597 0.5643 0.0815 0.045 Uiso 1 1 calc GR . . . .
H29B H 0.3328 0.7487 0.0337 0.045 Uiso 1 1 calc GR . . . .
H29C H 0.3077 0.5609 -0.0120 0.045 Uiso 1 1 calc GR . . . .
C26 C 0.21696(11) 0.6142(3) 0.29222(15) 0.0276(5) Uani 1 1 d . . . . .
H26A H 0.1782 0.5555 0.2867 0.041 Uiso 1 1 calc GR . . . .
H26B H 0.2159 0.7377 0.3133 0.041 Uiso 1 1 calc GR . . . .
H26C H 0.2495 0.5479 0.3349 0.041 Uiso 1 1 calc GR . . . .
C25 C 0.22818(10) 0.6165(3) 0.20385(14) 0.0203(4) Uani 1 1 d . . . . .
C27 C 0.11927(11) 0.7039(3) 0.10913(17) 0.0318(5) Uani 1 1 d . . . . .
H27A H 0.0942 0.6588 0.0513 0.048 Uiso 1 1 calc GR . . . .
H27B H 0.1152 0.8348 0.1110 0.048 Uiso 1 1 calc GR . . . .
H27C H 0.1060 0.6494 0.1569 0.048 Uiso 1 1 calc GR . . . .
F12A F 0.0000 0.177(2) 0.2500 0.079(4) Uiso 0.25 2 d S T P A 2
F14A F 0.0000 0.584(2) 0.2500 0.094(5) Uiso 0.25 2 d S T P A 2
F13A F -0.0669(5) 0.3689(17) 0.2446(7) 0.076(3) Uiso 0.25 1 d . . . A 2


_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 I2 2.69042(16) . ?
Ir1 C21 2.207(2) . ?
Ir1 C23 2.164(2) . ?
Ir1 N1 2.0624(17) . ?
Ir1 N8 2.0664(17) . ?
Ir1 C22 2.204(2) . ?
Ir1 C24 2.196(2) . ?
Ir1 C25 2.198(2) . ?
C21 C20 1.485(3) . ?
C21 C22 1.439(3) . ?
C21 C25 1.459(3) . ?
C6 N1 1.355(3) . ?
C6 C5 1.391(3) . ?
C6 N7 1.385(3) . ?
C23 C28 1.497(3) . ?
C23 C22 1.438(3) . ?
C23 C24 1.448(3) . ?
C9 C10 1.406(3) . ?
C9 N8 1.394(3) . ?
C9 C14 1.411(3) . ?
C12 O12 1.304(3) . ?
C12 C11 1.410(4) . ?
C12 C13 1.419(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C4 C3 1.382(4) . ?
N1 C2 1.347(3) . ?
C20 C19 1.391(4) . ?
C20 C15 1.392(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
O12 H12 0.8400 . ?
C5 H5 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.391(4) . ?
C11 H11 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.391(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.379(5) . ?
N8 N7 1.297(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.368(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?
C17 H17 0.9500 . ?
P10 F11 1.5929(18) . ?
P10 F11 1.5929(18) 2 ?
P10 F12 1.552(3) 2 ?
P10 F12 1.552(3) . ?
P10 F13 1.602(3) . ?
P10 F13 1.602(3) 2 ?
P10 F12A 1.438(15) . ?
P10 F14A 1.587(17) . ?
P10 F13A 1.528(11) . ?
P10 F13A 1.528(11) 2 ?
C22 C29 1.494(3) . ?
C24 C25 1.424(3) . ?
C24 C27 1.493(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C26 C25 1.486(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C21 Ir1 I2 104.82(5) . . ?
C23 Ir1 I2 160.60(6) . . ?
C23 Ir1 C21 64.64(8) . . ?
C23 Ir1 C22 38.43(8) . . ?
C23 Ir1 C24 38.79(8) . . ?
C23 Ir1 C25 64.58(8) . . ?
N1 Ir1 I2 85.80(5) . . ?
N1 Ir1 C21 161.66(7) . . ?
N1 Ir1 C23 100.64(8) . . ?
N1 Ir1 N8 75.11(7) . . ?
N1 Ir1 C22 134.32(7) . . ?
N1 Ir1 C24 97.66(7) . . ?
N1 Ir1 C25 126.42(8) . . ?
N8 Ir1 I2 90.32(5) . . ?
N8 Ir1 C21 118.94(7) . . ?
N8 Ir1 C23 108.99(8) . . ?
N8 Ir1 C22 97.23(7) . . ?
N8 Ir1 C24 146.12(7) . . ?
N8 Ir1 C25 157.62(8) . . ?
C22 Ir1 I2 139.79(6) . . ?
C22 Ir1 C21 38.07(8) . . ?
C24 Ir1 I2 122.58(6) . . ?
C24 Ir1 C21 64.05(8) . . ?
C24 Ir1 C22 63.86(8) . . ?
C24 Ir1 C25 37.82(8) . . ?
C25 Ir1 I2 96.81(6) . . ?
C25 Ir1 C21 38.70(8) . . ?
C25 Ir1 C22 63.98(8) . . ?
C20 C21 Ir1 133.40(16) . . ?
C22 C21 Ir1 70.87(11) . . ?
C22 C21 C20 125.0(2) . . ?
C22 C21 C25 107.16(18) . . ?
C25 C21 Ir1 70.34(11) . . ?
C25 C21 C20 126.67(19) . . ?
N1 C6 C5 121.9(2) . . ?
N1 C6 N7 117.65(18) . . ?
N7 C6 C5 120.3(2) . . ?
C28 C23 Ir1 125.08(16) . . ?
C22 C23 Ir1 72.30(12) . . ?
C22 C23 C28 125.8(2) . . ?
C22 C23 C24 107.48(18) . . ?
C24 C23 Ir1 71.80(12) . . ?
C24 C23 C28 126.5(2) . . ?
C10 C9 C14 119.2(2) . . ?
N8 C9 C10 118.77(19) . . ?
N8 C9 C14 122.05(19) . . ?
O12 C12 C11 119.5(3) . . ?
O12 C12 C13 122.3(3) . . ?
C11 C12 C13 118.2(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C6 N1 Ir1 113.67(14) . . ?
C2 N1 Ir1 127.07(16) . . ?
C2 N1 C6 119.25(19) . . ?
C19 C20 C21 117.8(2) . . ?
C19 C20 C15 118.9(2) . . ?
C15 C20 C21 123.3(2) . . ?
N1 C2 H2 119.6 . . ?
N1 C2 C3 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C12 O12 H12 109.5 . . ?
C6 C5 H5 120.9 . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 H5 120.9 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C20 C15 H15 119.8 . . ?
C16 C15 C20 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 120.0 . . ?
C9 N8 Ir1 125.55(13) . . ?
N7 N8 Ir1 118.56(13) . . ?
N7 N8 C9 115.59(17) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
N8 N7 C6 112.81(18) . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
F11 P10 F11 179.02(18) . 2 ?
F11 P10 F13 88.28(13) 2 . ?
F11 P10 F13 88.29(13) . 2 ?
F11 P10 F13 91.01(14) 2 2 ?
F11 P10 F13 91.00(14) . . ?
F12 P10 F11 91.00(15) . . ?
F12 P10 F11 89.66(16) 2 . ?
F12 P10 F11 91.00(15) 2 2 ?
F12 P10 F11 89.66(16) . 2 ?
F12 P10 F12 95.1(4) . 2 ?
F12 P10 F13 89.0(2) . . ?
F12 P10 F13 89.0(2) 2 2 ?
F12 P10 F13 175.8(3) . 2 ?
F12 P10 F13 175.8(3) 2 . ?
F13 P10 F13 87.0(3) 2 . ?
F12A P10 F11 89.51(9) . . ?
F12A P10 F11 89.51(9) . 2 ?
F12A P10 F14A 180.0 . . ?
F12A P10 F13A 89.6(5) . 2 ?
F12A P10 F13A 89.6(5) . . ?
F14A P10 F11 90.49(9) . . ?
F14A P10 F11 90.49(9) . 2 ?
F13A P10 F11 88.6(4) 2 2 ?
F13A P10 F11 91.4(4) . 2 ?
F13A P10 F11 88.6(4) . . ?
F13A P10 F11 91.4(4) 2 . ?
F13A P10 F14A 90.4(5) . . ?
F13A P10 F14A 90.4(5) 2 . ?
F13A P10 F13A 179.1(9) . 2 ?
C21 C22 Ir1 71.05(12) . . ?
C21 C22 C29 126.5(2) . . ?
C23 C22 Ir1 69.27(12) . . ?
C23 C22 C21 108.66(19) . . ?
C23 C22 C29 124.8(2) . . ?
C29 C22 Ir1 126.62(15) . . ?
C23 C24 Ir1 69.42(12) . . ?
C23 C24 C27 125.1(2) . . ?
C25 C24 Ir1 71.18(12) . . ?
C25 C24 C23 108.46(19) . . ?
C25 C24 C27 126.3(2) . . ?
C27 C24 Ir1 128.18(16) . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
C21 C25 Ir1 70.96(11) . . ?
C21 C25 C26 126.8(2) . . ?
C24 C25 Ir1 71.00(12) . . ?
C24 C25 C21 108.12(19) . . ?
C24 C25 C26 124.9(2) . . ?
C26 C25 Ir1 127.84(15) . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
O12 H12 O12 0.84 1.63 2.468(5) 172.7 3_655

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.115
_oxdiff_exptl_absorpt_empirical_full_min 0.691
####################################################################### 
# 
# 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_wz6
_database_code_depnum_ccdc_archive 'CCDC 1860994'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2018-08-08 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2017-09-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 Br I Ir N3 O, C H4 O, F6 P'
_chemical_formula_sum            'C22 H27 Br F6 I Ir N3 O2 P'
_chemical_formula_weight         909.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 Cl Rh'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.61097(8)
_cell_length_b                   20.10144(16)
_cell_length_c                   14.45419(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.4265(10)
_cell_angle_gamma                90
_cell_volume                     2716.14(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    39529
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.3490
_cell_measurement_theta_min      4.3620
_shelx_estimated_absorpt_T_max   0.361
_shelx_estimated_absorpt_T_min   0.131
_exptl_absorpt_coefficient_mu    21.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29026
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.330
_diffrn_reflns_theta_min         3.837
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  31.00   1.00    1.00    --  -42.36  37.00  90.00   96
  2  ω   -129.00  44.00   1.00    1.00    --  -42.36   0.00  30.00  173
  3  ω     20.00 115.00   1.00    1.00    --   42.36  37.00  30.00   95
  4  ω     97.00 178.00   1.00    4.00    --  106.00  83.00  65.00   81
  5  ω     25.00 109.00   1.00    4.00    --  106.00 -94.00 -90.00   84
  6  ω     35.00 130.00   1.00    4.00    --  106.00 -45.00 -90.00   95
  7  ω     82.00 178.00   1.00    4.00    --  106.00  30.00-150.00   96
  8  ω     82.00 177.00   1.00    4.00    --  106.00  45.00  30.00   95
  9  ω     25.00 109.00   1.00    4.00    --  106.00 -94.00  90.00   84
 10  ω     31.00 130.00   1.00    4.00    --  106.00 -30.00  60.00   99
 11  ω     82.00 178.00   1.00    4.00    --  106.00  30.00 150.00   96
 12  ω     34.00 121.00   1.00    4.00    --  106.00-125.00  90.00   87
 13  ω     25.00 109.00   1.00    4.00    --  106.00 -94.00-150.00   84
 14  ω     23.00  97.00   1.00    1.00    --   42.36-125.00-120.00   74
 15  ω     11.00 116.00   1.00    1.00    --   42.36  77.00  60.00  105
 16  ω     11.00 116.00   1.00    1.00    --   42.36  77.00 -90.00  105
 17  ω     11.00 116.00   1.00    1.00    --   42.36  77.00 150.00  105
 18  ω     78.00 176.00   1.00    4.00    --  106.00  61.00-150.00   98
 19  ω     78.00 176.00   1.00    4.00    --  106.00  61.00-120.00   98
 20  ω     78.00 176.00   1.00    4.00    --  106.00  61.00 -30.00   98
 21  ω     78.00 176.00   1.00    4.00    --  106.00  61.00 150.00   98
 22  ω     82.00 178.00   1.00    4.00    --  106.00  30.00 -60.00   96
 23  ω     78.00 176.00   1.00    4.00    --  106.00  61.00 -60.00   98
 24  ω     78.00 176.00   1.00    4.00    --  106.00  61.00  90.00   98
 25  ω     78.00 176.00   1.00    4.00    --  106.00  61.00  60.00   98
 26  ω   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00 -30.00  105
 27  ω     23.00  97.00   1.00    1.00    --   42.36-125.00 -30.00   74
 28  ω     16.00 113.00   1.00    1.00    --   42.36  57.00-120.00   97
 29  ω      1.00  82.00   1.00    1.00    --   42.36 -99.00-180.00   81
 30  ω     78.00 176.00   1.00    4.00    --  106.00  61.00  30.00   98
 31  ω     25.00 109.00   1.00    4.00    --  106.00 -94.00 150.00   84
 32  ω     78.00 176.00   1.00    4.00    --  106.00  61.00   0.00   98
 33  ω     78.00 117.00   1.00    4.00    --  106.00  61.00 120.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0448326000
_diffrn_orient_matrix_UB_12      0.0663629000
_diffrn_orient_matrix_UB_13      0.0517883000
_diffrn_orient_matrix_UB_21      -0.1492917000
_diffrn_orient_matrix_UB_22      0.0062506000
_diffrn_orient_matrix_UB_23      0.0213475000
_diffrn_orient_matrix_UB_31      0.0537155000
_diffrn_orient_matrix_UB_32      -0.0378477000
_diffrn_orient_matrix_UB_33      0.0940911000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5341
_reflns_number_total             5384
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         2.000
_refine_diff_density_min         -1.808
_refine_diff_density_rms         0.171
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.121
_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)+(0.0452P)²+4.5103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0772
_refine_special_details          ?
_olex2_refinement_description    
;
The OHs were located in a difference map but placed at calculated positions for the refinement.
The PF6 counter ion was modeled as disordered over two positions related by a rotation about the 
F11-P1-F12 axis. The occupancy of the two components was linked to a free variable which refined to 61:39

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) groups
2. Others
 Sof(F13A)=Sof(F15A)=Sof(F14A)=Sof(F16A)=1-FVAR(1)
 Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C02(H02A,H02B,H02C)
3.c Idealised tetrahedral OH refined as rotating group:
 O12(H12), O01(H01)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.11083(3) 0.29356(2) 0.61717(2) 0.02093(8) Uani 1 1 d . . . . .
Ir1 Ir 0.96984(2) 0.33337(2) 0.74719(2) 0.01115(7) Uani 1 1 d . . . . .
N1 N 0.9236(3) 0.41996(15) 0.6669(2) 0.0121(6) Uani 1 1 d . . . . .
C2 C 1.0012(4) 0.47593(18) 0.6741(3) 0.0151(7) Uani 1 1 d . . . . .
H2 H 1.0889 0.4790 0.7206 0.018 Uiso 1 1 calc R . . . .
Br3 Br 1.06634(5) 0.60757(2) 0.62937(3) 0.02370(11) Uani 1 1 d . . . . .
C3 C 0.9548(4) 0.52944(18) 0.6142(3) 0.0159(7) Uani 1 1 d . . . . .
C4 C 0.8291(4) 0.52670(19) 0.5445(3) 0.0185(8) Uani 1 1 d . . . . .
H4 H 0.7976 0.5637 0.5042 0.022 Uiso 1 1 calc R . . . .
C5 C 0.7500(4) 0.4680(2) 0.5352(3) 0.0187(8) Uani 1 1 d . . . . .
H5 H 0.6641 0.4633 0.4874 0.022 Uiso 1 1 calc R . . . .
C6 C 0.8008(4) 0.41638(19) 0.5982(3) 0.0145(7) Uani 1 1 d . . . . .
N7 N 0.7238(3) 0.35764(16) 0.5897(2) 0.0152(6) Uani 1 1 d . . . . .
N8 N 0.7834(3) 0.31390(16) 0.6500(2) 0.0128(6) Uani 1 1 d . . . . .
C9 C 0.7024(4) 0.25407(18) 0.6467(3) 0.0141(7) Uani 1 1 d . . . . .
C10 C 0.5547(4) 0.25700(19) 0.6348(3) 0.0167(7) Uani 1 1 d . . . . .
H10 H 0.5066 0.2986 0.6247 0.020 Uiso 1 1 calc R . . . .
C11 C 0.4781(4) 0.1991(2) 0.6378(3) 0.0193(8) Uani 1 1 d . . . . .
H11 H 0.3778 0.2009 0.6326 0.023 Uiso 1 1 calc R . . . .
C12 C 0.5496(4) 0.13746(18) 0.6486(3) 0.0154(7) Uani 1 1 d . . . . .
O12 O 0.4784(3) 0.07952(14) 0.6514(2) 0.0210(6) Uani 1 1 d . . . . .
H12 H 0.3902 0.0871 0.6410 0.032 Uiso 1 1 calc GR . . . .
C13 C 0.6971(4) 0.13473(19) 0.6586(3) 0.0176(7) Uani 1 1 d . . . . .
H13 H 0.7450 0.0930 0.6655 0.021 Uiso 1 1 calc R . . . .
C14 C 0.7736(4) 0.19286(19) 0.6585(3) 0.0169(7) Uani 1 1 d . . . . .
H14 H 0.8745 0.1913 0.6665 0.020 Uiso 1 1 calc R . . . .
C15 C 0.9092(5) 0.2980(2) 0.8752(3) 0.0210(8) Uani 1 1 d . . . . .
C16 C 1.0279(5) 0.25852(19) 0.8598(3) 0.0213(8) Uani 1 1 d . . . . .
C17 C 1.1474(4) 0.3028(2) 0.8684(3) 0.0187(8) Uani 1 1 d . . . . .
C18 C 1.1049(4) 0.36805(19) 0.8849(3) 0.0153(7) Uani 1 1 d . . . . .
C19 C 0.9542(4) 0.3659(2) 0.8875(3) 0.0165(7) Uani 1 1 d . . . . .
C20 C 0.8715(5) 0.4241(2) 0.9100(3) 0.0245(9) Uani 1 1 d . . . . .
H20A H 0.8948 0.4635 0.8768 0.037 Uiso 1 1 calc GR . . . .
H20B H 0.8965 0.4321 0.9788 0.037 Uiso 1 1 calc GR . . . .
H20C H 0.7689 0.4148 0.8894 0.037 Uiso 1 1 calc GR . . . .
C21 C 1.1975(5) 0.4282(2) 0.9068(3) 0.0216(8) Uani 1 1 d . . . . .
H21A H 1.2714 0.4268 0.8702 0.032 Uiso 1 1 calc GR . . . .
H21B H 1.2429 0.4291 0.9749 0.032 Uiso 1 1 calc GR . . . .
H21C H 1.1389 0.4682 0.8898 0.032 Uiso 1 1 calc GR . . . .
C22 C 1.2968(5) 0.2823(3) 0.8657(3) 0.0313(10) Uani 1 1 d . . . . .
H22A H 1.2928 0.2447 0.8219 0.047 Uiso 1 1 calc GR . . . .
H22B H 1.3490 0.2690 0.9296 0.047 Uiso 1 1 calc GR . . . .
H22C H 1.3460 0.3197 0.8438 0.047 Uiso 1 1 calc GR . . . .
C23 C 1.0355(6) 0.1839(2) 0.8543(4) 0.0381(12) Uani 1 1 d . . . . .
H23A H 0.9387 0.1657 0.8333 0.057 Uiso 1 1 calc GR . . . .
H23B H 1.0805 0.1660 0.9172 0.057 Uiso 1 1 calc GR . . . .
H23C H 1.0924 0.1713 0.8089 0.057 Uiso 1 1 calc GR . . . .
C24 C 0.7659(5) 0.2710(3) 0.8804(3) 0.0308(10) Uani 1 1 d . . . . .
H24A H 0.6928 0.3054 0.8601 0.046 Uiso 1 1 calc GR . . . .
H24B H 0.7681 0.2578 0.9460 0.046 Uiso 1 1 calc GR . . . .
H24C H 0.7430 0.2323 0.8385 0.046 Uiso 1 1 calc GR . . . .
O01 O 0.1982(3) 0.09413(18) 0.6430(2) 0.0322(7) Uani 1 1 d . . . . .
H01 H 0.1628 0.0756 0.6843 0.048 Uiso 1 1 calc GR . . . .
C02 C 0.0939(5) 0.0976(3) 0.5560(3) 0.0318(10) Uani 1 1 d . . . . .
H02A H 0.0845 0.0540 0.5249 0.048 Uiso 1 1 calc GR . . . .
H02B H 0.1232 0.1306 0.5144 0.048 Uiso 1 1 calc GR . . . .
H02C H 0.0017 0.1107 0.5686 0.048 Uiso 1 1 calc GR . . . .
P10 P 0.49210(11) 0.46719(5) 0.72478(7) 0.0180(2) Uani 1 1 d . . . . .
F11 F 0.4612(4) 0.4451(2) 0.6175(2) 0.0579(11) Uani 1 1 d . . . . .
F12 F 0.5250(4) 0.4885(3) 0.8335(2) 0.0775(15) Uani 1 1 d . . . . .
F13 F 0.3395(6) 0.4370(4) 0.7238(4) 0.054(2) Uani 0.612(11) 1 d . . P A 1
F14 F 0.6469(7) 0.4954(4) 0.7282(4) 0.0470(19) Uani 0.612(11) 1 d . . P A 1
F15 F 0.4230(8) 0.5383(3) 0.7032(4) 0.056(2) Uani 0.612(11) 1 d . . P A 1
F16 F 0.5627(8) 0.3945(3) 0.7479(4) 0.046(2) Uani 0.612(11) 1 d . . P A 1
F13A F 0.3341(9) 0.4910(7) 0.7181(8) 0.061(4) Uani 0.388(11) 1 d . . P A 2
F15A F 0.5202(15) 0.5322(5) 0.6691(8) 0.070(4) Uani 0.388(11) 1 d . . P A 2
F14A F 0.6531(10) 0.4456(10) 0.7307(7) 0.074(6) Uani 0.388(11) 1 d . . P A 2
F16A F 0.4737(18) 0.4031(6) 0.7796(9) 0.076(5) Uani 0.388(11) 1 d . . P A 2


_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
I1 Ir1 2.6817(3) . ?
Ir1 N1 2.082(3) . ?
Ir1 N8 2.042(3) . ?
Ir1 C15 2.183(4) . ?
Ir1 C16 2.192(4) . ?
Ir1 C17 2.230(4) . ?
Ir1 C18 2.221(4) . ?
Ir1 C19 2.169(4) . ?
N1 C2 1.341(5) . ?
N1 C6 1.356(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
Br3 C3 1.885(4) . ?
C3 C4 1.383(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(5) . ?
C6 N7 1.384(5) . ?
N7 N8 1.277(5) . ?
N8 C9 1.427(5) . ?
C9 C10 1.391(6) . ?
C9 C14 1.399(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.408(6) . ?
C12 O12 1.356(5) . ?
C12 C13 1.392(6) . ?
O12 H12 0.8400 . ?
C13 H13 0.9500 . ?
C13 C14 1.380(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.448(6) . ?
C15 C19 1.430(6) . ?
C15 C24 1.498(6) . ?
C16 C17 1.435(6) . ?
C16 C23 1.505(6) . ?
C17 C18 1.410(6) . ?
C17 C22 1.503(6) . ?
C18 C19 1.459(5) . ?
C18 C21 1.490(5) . ?
C19 C20 1.492(6) . ?
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 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O01 H01 0.8400 . ?
O01 C02 1.415(6) . ?
C02 H02A 0.9800 . ?
C02 H02B 0.9800 . ?
C02 H02C 0.9800 . ?
P10 F11 1.574(3) . ?
P10 F12 1.589(3) . ?
P10 F13 1.584(5) . ?
P10 F14 1.582(5) . ?
P10 F15 1.577(5) . ?
P10 F16 1.612(5) . ?
P10 F13A 1.574(8) . ?
P10 F15A 1.590(9) . ?
P10 F14A 1.591(9) . ?
P10 F16A 1.545(10) . ?

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 I1 86.35(8) . . ?
N1 Ir1 C15 132.85(15) . . ?
N1 Ir1 C16 166.55(13) . . ?
N1 Ir1 C17 133.94(14) . . ?
N1 Ir1 C18 103.99(13) . . ?
N1 Ir1 C19 102.54(13) . . ?
N8 Ir1 I1 88.07(8) . . ?
N8 Ir1 N1 74.77(12) . . ?
N8 Ir1 C15 98.97(14) . . ?
N8 Ir1 C16 114.25(15) . . ?
N8 Ir1 C17 151.29(14) . . ?
N8 Ir1 C18 156.03(13) . . ?
N8 Ir1 C19 117.43(14) . . ?
C15 Ir1 I1 140.72(12) . . ?
C15 Ir1 C16 38.67(17) . . ?
C15 Ir1 C17 63.30(16) . . ?
C15 Ir1 C18 63.81(15) . . ?
C16 Ir1 I1 103.44(12) . . ?
C16 Ir1 C17 37.87(16) . . ?
C16 Ir1 C18 63.57(14) . . ?
C17 Ir1 I1 92.82(11) . . ?
C18 Ir1 I1 115.86(10) . . ?
C18 Ir1 C17 36.95(15) . . ?
C19 Ir1 I1 154.31(11) . . ?
C19 Ir1 C15 38.37(16) . . ?
C19 Ir1 C16 64.75(15) . . ?
C19 Ir1 C17 63.57(15) . . ?
C19 Ir1 C18 38.79(14) . . ?
C2 N1 Ir1 128.0(3) . . ?
C2 N1 C6 118.3(3) . . ?
C6 N1 Ir1 113.6(2) . . ?
N1 C2 H2 119.7 . . ?
N1 C2 C3 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 Br3 118.8(3) . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 Br3 119.7(3) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.9(4) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C5 123.6(4) . . ?
N1 C6 N7 117.8(3) . . ?
N7 C6 C5 118.6(3) . . ?
N8 N7 C6 112.4(3) . . ?
N7 N8 Ir1 121.4(3) . . ?
N7 N8 C9 113.7(3) . . ?
C9 N8 Ir1 124.7(2) . . ?
C10 C9 N8 120.1(3) . . ?
C10 C9 C14 120.6(3) . . ?
C14 C9 N8 119.3(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
O12 C12 C11 121.5(4) . . ?
O12 C12 C13 118.2(3) . . ?
C13 C12 C11 120.3(4) . . ?
C12 O12 H12 109.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.9(4) . . ?
C13 C14 H14 120.0 . . ?
C16 C15 Ir1 71.0(2) . . ?
C16 C15 C24 125.2(4) . . ?
C19 C15 Ir1 70.3(2) . . ?
C19 C15 C16 108.4(4) . . ?
C19 C15 C24 126.4(4) . . ?
C24 C15 Ir1 126.1(3) . . ?
C15 C16 Ir1 70.4(2) . . ?
C15 C16 C23 127.1(4) . . ?
C17 C16 Ir1 72.5(2) . . ?
C17 C16 C15 106.9(3) . . ?
C17 C16 C23 125.1(4) . . ?
C23 C16 Ir1 130.7(3) . . ?
C16 C17 Ir1 69.6(2) . . ?
C16 C17 C22 125.3(4) . . ?
C18 C17 Ir1 71.2(2) . . ?
C18 C17 C16 109.5(4) . . ?
C18 C17 C22 125.1(4) . . ?
C22 C17 Ir1 128.1(3) . . ?
C17 C18 Ir1 71.9(2) . . ?
C17 C18 C19 107.7(3) . . ?
C17 C18 C21 127.5(4) . . ?
C19 C18 Ir1 68.7(2) . . ?
C19 C18 C21 124.5(4) . . ?
C21 C18 Ir1 129.9(3) . . ?
C15 C19 Ir1 71.4(2) . . ?
C15 C19 C18 107.4(4) . . ?
C15 C19 C20 127.9(4) . . ?
C18 C19 Ir1 72.5(2) . . ?
C18 C19 C20 124.4(4) . . ?
C20 C19 Ir1 126.6(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 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 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C02 O01 H01 109.5 . . ?
O01 C02 H02A 109.5 . . ?
O01 C02 H02B 109.5 . . ?
O01 C02 H02C 109.5 . . ?
H02A C02 H02B 109.5 . . ?
H02A C02 H02C 109.5 . . ?
H02B C02 H02C 109.5 . . ?
F11 P10 F12 179.1(2) . . ?
F11 P10 F13 85.4(3) . . ?
F11 P10 F14 95.3(3) . . ?
F11 P10 F15 94.9(3) . . ?
F11 P10 F16 85.6(3) . . ?
F11 P10 F13A 93.8(4) . . ?
F11 P10 F15A 75.4(5) . . ?
F11 P10 F14A 86.3(4) . . ?
F12 P10 F16 93.5(3) . . ?
F12 P10 F15A 105.2(5) . . ?
F12 P10 F14A 93.0(4) . . ?
F13 P10 F12 94.8(3) . . ?
F13 P10 F16 89.9(4) . . ?
F14 P10 F12 84.5(3) . . ?
F14 P10 F13 178.1(4) . . ?
F14 P10 F16 88.3(4) . . ?
F15 P10 F12 86.0(3) . . ?
F15 P10 F13 90.0(4) . . ?
F15 P10 F14 91.8(4) . . ?
F15 P10 F16 179.5(3) . . ?
F13A P10 F12 86.9(4) . . ?
F13A P10 F15A 89.7(7) . . ?
F13A P10 F14A 178.1(9) . . ?
F15A P10 F14A 88.5(8) . . ?
F16A P10 F11 104.6(5) . . ?
F16A P10 F12 74.8(5) . . ?
F16A P10 F13A 93.6(8) . . ?
F16A P10 F15A 176.8(8) . . ?
F16A P10 F14A 88.3(9) . . ?

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
O12 H12 O01 0.84 1.86 2.684(4) 167.4 .
O01 H01 F13A 0.84 2.20 2.951(12) 148.1 2_546

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.977
_oxdiff_exptl_absorpt_empirical_full_min 0.465
####################################################################### 
# 
# 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_wz10
_database_code_depnum_ccdc_archive 'CCDC 1860995'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2018-08-08 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled Apr  3 2018 11:26:26 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 F3 I Ir N3 O, F6 P, C H4 O'
_chemical_formula_sum            'C23 H27 F9 I Ir N3 O2 P'
_chemical_formula_weight         898.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 Ir'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.85870(10)
_cell_length_b                   20.2807(2)
_cell_length_c                   15.0835(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.2450(10)
_cell_angle_gamma                90
_cell_volume                     2909.69(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11692
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      77.6370
_cell_measurement_theta_min      4.6180
_shelx_estimated_absorpt_T_max   0.319
_shelx_estimated_absorpt_T_min   0.095
_exptl_absorpt_coefficient_mu    18.514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark purple'
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16591
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.991
_diffrn_reflns_theta_min         3.738
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -116.00 -17.00 1.00 10.00 -- -41.71 -38.00 60.00 99 2 ω -130.00 46.00 1.00 10.00 -- -41.71 0.00-120.00 176 3 ω 18.00 98.00 1.00 10.00 -- 41.71-125.00 90.00 80 4 ω 18.00 98.00 1.00 10.00 -- 41.71-125.00 -60.00 80 5 ω 88.00 178.00 1.00 50.00 -- 114.00 45.00 -90.00 90 6 ω 57.00 151.00 1.00 50.00 -- 114.00 178.00-180.00 94 7 ω 38.00 91.00 1.00 50.00 -- 114.00 -30.00 -90.00 53 8 ω 100.00 178.00 1.00 50.00 -- 114.00 111.00 0.00 78 9 ω 38.00 91.00 1.00 50.00 -- 114.00 -30.00 90.00 53 10 ω 38.00 91.00 1.00 50.00 -- 114.00 -30.00 120.00 53 11 ω 100.00 178.00 1.00 50.00 -- 114.00 111.00-120.00 78 12 ω 41.00 99.00 1.00 50.00 -- 114.00 -45.00 -30.00 58 13 ω 38.00 88.00 1.00 50.00 -- 114.00-111.00 -30.00 50'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1270385000
_diffrn_orient_matrix_UB_12      0.0024116000
_diffrn_orient_matrix_UB_13      0.0414414000
_diffrn_orient_matrix_UB_21      0.0605839000
_diffrn_orient_matrix_UB_22      -0.0586786000
_diffrn_orient_matrix_UB_23      0.0628612000
_diffrn_orient_matrix_UB_31      0.0801148000
_diffrn_orient_matrix_UB_32      0.0481656000
_diffrn_orient_matrix_UB_33      0.0744439000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5698
_reflns_number_total             6029
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.915
_refine_diff_density_min         -1.713
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6029
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.057
_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)+(0.1029P)²+1.4618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1404
_refine_special_details          ?
_olex2_refinement_description    
;
The OH hydrogens were placed at calculated positions.
The PF6 was modeled over two positions related by a rotation about P10. The occupancy of the two components 
was linked to a free variable which refined to 73:27. The minor component was refined isotropically.
The Cp* was modeled as disordered over two positions related by a rotation about the bond to Ir1. 
The occupancy of the two components was originally linked to a free variable but fixed at 70:30 for the refinement. 
Both Cp* rings were refined with geometric restraints (AFIX 105) to give them idealized bond lengths and angles and 
a RIGU restraint was used to give reasonable thermal parameters for the methyl group of the major component.

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) groups
2. Restrained distances
 P10-F11 = P10-F12 = P10-F13 = P10-F14 = P10-F15 = P10-F16
 1.6 with sigma of 0.02
 P10-F11A = P10-F12A = P10-F13A = P10-F14A = P10-F0AA = P10-F16A
 1.6 with sigma of 0.02
 H14-H21E
 -1.9 with sigma of 0.02
 F11-F13 = F11-F14 = F11-F15 = F11-F16
 2.26 with sigma of 0.04
 F12-F13 = F12-F14 = F12-F15 = F12-F16
 2.26 with sigma of 0.04
 F13-F15 = F13-F16 = F14-F15 = F14-F16
 2.26 with sigma of 0.04
 F11A-F13A = F11A-F14A = F11A-F0AA = F11A-F16A
 2.26 with sigma of 0.04
 F12A-F13A = F12A-F14A = F12A-F0AA = F12A-F16A
 2.26 with sigma of 0.04
 F13A-F0AA = F13A-F16A = F14A-F0AA = F14A-F16A
 2.26 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C23, C24, C25, C21, C22, C20, C16, C17, C18, C19
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(F13A)=Sof(F16A)=Sof(F12A)=Sof(F14A)=Sof(F0AA)=Sof(F11A)=1-FVAR(1)
 Sof(F14)=Sof(F13)=Sof(F15)=Sof(F11)=Sof(F16)=Sof(F12)=FVAR(1)
 Fixed Sof: C20(0.7) C16(0.7) C17(0.7) C18(0.7) C19(0.7) C25(0.7) H25A(0.7)
 H25B(0.7) H25C(0.7) C21(0.7) H21A(0.7) H21B(0.7) H21C(0.7) C22(0.7) H22A(0.7)
 H22B(0.7) H22C(0.7) C23(0.7) H23A(0.7) H23B(0.7) H23C(0.7) C24(0.7) H24A(0.7)
 H24B(0.7) H24C(0.7) C16A(0.3) C17A(0.3) C18A(0.3) C19A(0.3) C20A(0.3)
 C21A(0.3) H21D(0.3) H21E(0.3) H21F(0.3) C22A(0.3) H22D(0.3) H22E(0.3)
 H22F(0.3) C23A(0.3) H23D(0.3) H23E(0.3) H23F(0.3) C24A(0.3) H24D(0.3)
 H24E(0.3) H24F(0.3) C25A(0.3) H25D(0.3) H25E(0.3) H25F(0.3)
5.a Me refined with riding coordinates:
 C21A(H21D,H21E,H21F)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C2(H2), C13(H13), C10(H10), C11(H11), C14(H14)
5.c Cp* refined as free rotating group:
 C20(C16,C17,C18,C19,C25,C21,C22,C23,C24), C16A(C17A,C18A,C19A,C20A,C21A,C22A,
 C23A,C24A,C25A)
5.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C22A(H22D,H22E,H22F),
 C23A(H23D,H23E,H23F), C24A(H24D,H24E,H24F), C25A(H25D,H25E,H25F)
5.e Idealised tetrahedral OH refined as rotating group:
 O12(H12), O26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.04844(2) 0.67735(2) 0.25476(2) 0.04543(12) Uani 1 1 d . . . . .
I1 I -0.09016(5) 0.71678(3) 0.37626(3) 0.07461(16) Uani 1 1 d . . . . .
P10 P 0.51735(19) 0.53436(10) 0.27602(13) 0.0692(4) Uani 1 1 d D . . . .
F15C F -0.1323(6) 0.4209(3) 0.3075(4) 0.0966(16) Uani 1 1 d . . . . .
F15B F -0.0474(8) 0.4058(3) 0.4507(4) 0.109(2) Uani 1 1 d . . . . .
N8 N 0.2330(5) 0.6965(2) 0.3492(3) 0.0475(9) Uani 1 1 d . . . . .
O12 O 0.5351(6) 0.9282(2) 0.3636(4) 0.0698(11) Uani 1 1 d . . . . .
H12 H 0.617182 0.920591 0.364532 0.105 Uiso 1 1 calc GR . . . .
N1 N 0.0963(4) 0.5916(2) 0.3325(3) 0.0441(8) Uani 1 1 d . . . . .
N7 N 0.2949(5) 0.6528(2) 0.4072(3) 0.0508(9) Uani 1 1 d . . . . .
F15A F 0.0570(6) 0.3685(2) 0.3564(4) 0.0924(15) Uani 1 1 d . . . . .
C4 C 0.1969(7) 0.4852(3) 0.4483(4) 0.0579(13) Uani 1 1 d . . . . .
H4 H 0.229313 0.449135 0.485974 0.069 Uiso 1 1 calc R . . . .
C5 C 0.2734(7) 0.5422(3) 0.4573(4) 0.0585(13) Uani 1 1 d . . . . .
H5 H 0.358698 0.546036 0.501620 0.070 Uiso 1 1 calc R . . . .
C6 C 0.2198(5) 0.5948(3) 0.3978(3) 0.0469(10) Uani 1 1 d . . . . .
C3 C 0.0695(6) 0.4825(3) 0.3816(3) 0.0491(10) Uani 1 1 d . . . . .
C9 C 0.3136(5) 0.7559(3) 0.3553(3) 0.0457(10) Uani 1 1 d . . . . .
C2 C 0.0213(5) 0.5357(3) 0.3263(3) 0.0473(10) Uani 1 1 d . . . . .
H2 H -0.065581 0.532962 0.283266 0.057 Uiso 1 1 calc R . . . .
C15 C -0.0149(7) 0.4194(3) 0.3740(4) 0.0589(13) Uani 1 1 d . . . . .
C12 C 0.4656(7) 0.8708(3) 0.3622(4) 0.0539(12) Uani 1 1 d . . . . .
C13 C 0.3213(7) 0.8735(3) 0.3506(4) 0.0574(13) Uani 1 1 d . . . . .
H13 H 0.276155 0.914128 0.345724 0.069 Uiso 1 1 calc R . . . .
F14 F 0.6766(9) 0.5477(9) 0.2812(10) 0.156(5) Uani 0.729(15) 1 d D . P A 1
O26 O 0.8094(6) 0.9188(5) 0.3790(6) 0.108(2) Uani 1 1 d . . . . .
H26 H 0.842440 0.933646 0.338584 0.161 Uiso 1 1 calc GR . . . .
C10 C 0.4585(6) 0.7524(3) 0.3681(4) 0.0555(12) Uani 1 1 d . . . . .
H10 H 0.503901 0.711795 0.374718 0.067 Uiso 1 1 calc R . . . .
C11 C 0.5340(7) 0.8104(3) 0.3709(5) 0.0592(13) Uani 1 1 d . . . . .
H11 H 0.630660 0.808745 0.378613 0.071 Uiso 1 1 calc R . . . .
C20 C 0.1161(5) 0.7024(2) 0.1273(3) 0.0500(14) Uani 0.7 1 d . U P B 1
C16 C 0.0526(5) 0.63908(18) 0.1187(3) 0.0425(15) Uani 0.7 1 d G U P B 1
C17 C -0.0889(5) 0.6469(2) 0.1224(4) 0.058(2) Uani 0.7 1 d G U P B 1
C18 C -0.1129(5) 0.7151(3) 0.1332(4) 0.071(2) Uani 0.7 1 d G U P B 1
C19 C 0.0138(6) 0.74944(18) 0.1362(3) 0.0647(18) Uani 0.7 1 d G U P B 1
C25 C 0.2660(6) 0.7172(3) 0.1269(4) 0.071(2) Uani 0.7 1 d G U P B 1
H25A H 0.325586 0.713812 0.188265 0.106 Uiso 0.7 1 calc GR . P B 1
H25B H 0.271553 0.761057 0.104107 0.106 Uiso 0.7 1 calc GR . P B 1
H25C H 0.296175 0.686144 0.087951 0.106 Uiso 0.7 1 calc GR . P B 1
C21 C 0.1232(7) 0.5747(2) 0.1077(5) 0.062(2) Uani 0.7 1 d G U P B 1
H21A H 0.222450 0.581728 0.117965 0.093 Uiso 0.7 1 calc GR . P B 1
H21B H 0.085006 0.558094 0.046593 0.093 Uiso 0.7 1 calc GR . P B 1
H21C H 0.107109 0.543294 0.151445 0.093 Uiso 0.7 1 calc GR . P B 1
C22 C -0.1952(6) 0.5924(3) 0.1160(6) 0.112(6) Uani 0.7 1 d G U P B 1
H22A H -0.155353 0.558110 0.158884 0.169 Uiso 0.7 1 calc GR . P B 1
H22B H -0.220068 0.574683 0.054810 0.169 Uiso 0.7 1 calc GR . P B 1
H22C H -0.277686 0.609596 0.130220 0.169 Uiso 0.7 1 calc GR . P B 1
C23 C -0.2492(6) 0.7458(4) 0.1403(6) 0.125(6) Uani 0.7 1 d G U P B 1
H23A H -0.302285 0.713969 0.164322 0.187 Uiso 0.7 1 calc GR . P B 1
H23B H -0.302622 0.759729 0.080499 0.187 Uiso 0.7 1 calc GR . P B 1
H23C H -0.229309 0.783220 0.180661 0.187 Uiso 0.7 1 calc GR . P B 1
C24 C 0.0358(9) 0.82296(18) 0.1470(5) 0.113(6) Uani 0.7 1 d G U P B 1
H24A H -0.038049 0.841958 0.169376 0.170 Uiso 0.7 1 calc GR . P B 1
H24B H 0.034717 0.842082 0.088627 0.170 Uiso 0.7 1 calc GR . P B 1
H24C H 0.124858 0.831602 0.189981 0.170 Uiso 0.7 1 calc GR . P B 1
C14 C 0.2449(7) 0.8163(3) 0.3464(5) 0.0569(13) Uani 1 1 d . . . . .
H14 H 0.147988 0.818068 0.337714 0.068 Uiso 1 1 calc DR . . . .
F13 F 0.3580(8) 0.5140(7) 0.2686(8) 0.129(4) Uani 0.729(15) 1 d D . P A 1
F15 F 0.4860(15) 0.5239(9) 0.1701(6) 0.162(6) Uani 0.729(15) 1 d D . P A 1
C27 C 0.9178(11) 0.9092(6) 0.4597(7) 0.101(3) Uani 1 1 d . . . . .
H27A H 1.006086 0.905585 0.444319 0.152 Uiso 1 1 calc GR . . . .
H27B H 0.900466 0.869500 0.489505 0.152 Uiso 1 1 calc GR . . . .
H27C H 0.921027 0.946009 0.500203 0.152 Uiso 1 1 calc GR . . . .
F11 F 0.465(2) 0.6053(5) 0.2611(10) 0.195(9) Uani 0.729(15) 1 d D . P A 1
F16 F 0.5428(12) 0.5458(10) 0.3825(6) 0.167(7) Uani 0.729(15) 1 d D . P A 1
F12 F 0.5659(16) 0.4612(6) 0.2950(15) 0.220(10) Uani 0.729(15) 1 d D . P A 1
F13A F 0.495(3) 0.4802(11) 0.3450(16) 0.113(8) Uiso 0.271(15) 1 d D . P A 2
F16A F 0.672(2) 0.5098(16) 0.284(2) 0.141(14) Uiso 0.271(15) 1 d D . P A 2
F12A F 0.458(4) 0.4857(15) 0.1932(19) 0.18(2) Uiso 0.271(15) 1 d D . P A 2
F14A F 0.528(3) 0.5906(13) 0.2044(18) 0.136(11) Uiso 0.271(15) 1 d D . P A 2
F0AA F 0.3644(15) 0.5621(10) 0.2706(12) 0.078(5) Uiso 0.271(15) 1 d D . P A 2
F11A F 0.571(3) 0.5844(12) 0.3584(16) 0.119(9) Uiso 0.271(15) 1 d D . P A 2
C16A C -0.0419(12) 0.7507(5) 0.1480(7) 0.070(6) Uiso 0.3 1 d . . P B 2
C17A C 0.0750(11) 0.7160(6) 0.1328(9) 0.054(5) Uiso 0.3 1 d G . P B 2
C18A C 0.0345(11) 0.6492(5) 0.1139(9) 0.075(8) Uiso 0.3 1 d G . P B 2
C19A C -0.1074(10) 0.6426(5) 0.1174(8) 0.061(6) Uiso 0.3 1 d G . P B 2
C20A C -0.1546(11) 0.7054(5) 0.1384(8) 0.051(4) Uiso 0.3 1 d G . P B 2
C21A C -0.0457(17) 0.8231(5) 0.1704(11) 0.109(12) Uiso 0.3 1 d G . P B 2
H21D H -0.136988 0.834310 0.177320 0.163 Uiso 0.3 1 calc R . P B 2
H21E H 0.024202 0.832386 0.226544 0.163 Uiso 0.3 1 calc DR . P B 2
H21F H -0.026821 0.848737 0.121425 0.163 Uiso 0.3 1 calc R . P B 2
C22A C 0.2173(13) 0.7450(8) 0.1362(14) 0.097(10) Uiso 0.3 1 d G . P B 2
H22D H 0.206416 0.790212 0.116981 0.145 Uiso 0.3 1 calc GR . P B 2
H22E H 0.259621 0.720598 0.095873 0.145 Uiso 0.3 1 calc GR . P B 2
H22F H 0.276266 0.742484 0.197860 0.145 Uiso 0.3 1 calc GR . P B 2
C23A C 0.1263(14) 0.5947(7) 0.0936(14) 0.058(5) Uiso 0.3 1 d G . P B 2
H23D H 0.217894 0.597377 0.135781 0.087 Uiso 0.3 1 calc GR . P B 2
H23E H 0.134392 0.599221 0.031857 0.087 Uiso 0.3 1 calc GR . P B 2
H23F H 0.084848 0.552733 0.100277 0.087 Uiso 0.3 1 calc GR . P B 2
C24A C -0.1930(13) 0.5800(5) 0.1015(12) 0.036(3) Uiso 0.3 1 d G . P B 2
H24D H -0.131002 0.542595 0.111880 0.054 Uiso 0.3 1 calc GR . P B 2
H24E H -0.250619 0.579084 0.039312 0.054 Uiso 0.3 1 calc GR . P B 2
H24F H -0.251759 0.578324 0.143042 0.054 Uiso 0.3 1 calc GR . P B 2
C25A C -0.2993(13) 0.7212(7) 0.1489(13) 0.076(7) Uiso 0.3 1 d G . P B 2
H25D H -0.343352 0.681375 0.161760 0.114 Uiso 0.3 1 calc GR . P B 2
H25E H -0.355090 0.740362 0.092983 0.114 Uiso 0.3 1 calc GR . P B 2
H25F H -0.291384 0.751742 0.198558 0.114 Uiso 0.3 1 calc GR . P B 2


_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 I1 2.6799(5) . ?
Ir1 N8 2.032(4) . ?
Ir1 N1 2.082(4) . ?
Ir1 C20 2.253(4) . ?
Ir1 C16 2.204(4) . ?
Ir1 C17 2.185(5) . ?
Ir1 C18 2.223(4) . ?
Ir1 C19 2.265(4) . ?
Ir1 C16A 2.202(10) . ?
Ir1 C17A 2.078(12) . ?
Ir1 C18A 2.170(12) . ?
Ir1 C19A 2.340(11) . ?
Ir1 C20A 2.358(11) . ?
P10 F14 1.575(8) . ?
P10 F13 1.600(8) . ?
P10 F15 1.560(8) . ?
P10 F11 1.525(9) . ?
P10 F16 1.576(9) . ?
P10 F12 1.562(10) . ?
P10 F13A 1.569(15) . ?
P10 F16A 1.581(17) . ?
P10 F12A 1.579(17) . ?
P10 F14A 1.593(16) . ?
P10 F0AA 1.591(13) . ?
P10 F11A 1.583(16) . ?
F15C C15 1.318(9) . ?
F15B C15 1.308(7) . ?
N8 N7 1.282(6) . ?
N8 C9 1.432(7) . ?
O12 H12 0.8200 . ?
O12 C12 1.348(8) . ?
N1 C6 1.351(6) . ?
N1 C2 1.344(7) . ?
N7 C6 1.375(8) . ?
F15A C15 1.319(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(9) . ?
C4 C3 1.388(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(7) . ?
C3 C2 1.369(7) . ?
C3 C15 1.515(9) . ?
C9 C10 1.392(8) . ?
C9 C14 1.390(7) . ?
C2 H2 0.9300 . ?
C12 C13 1.388(9) . ?
C12 C11 1.388(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(9) . ?
O26 H26 0.8200 . ?
O26 C27 1.406(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(9) . ?
C11 H11 0.9300 . ?
C20 C16 1.4200 . ?
C20 C19 1.4200 . ?
C20 C25 1.5095 . ?
C16 C17 1.4200 . ?
C16 C21 1.5095 . ?
C17 C18 1.4200 . ?
C17 C22 1.5095 . ?
C18 C19 1.4200 . ?
C18 C23 1.5095 . ?
C19 C24 1.5095 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C14 H14 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C16A C17A 1.4200 . ?
C16A C20A 1.4200 . ?
C16A C21A 1.5095 . ?
C17A C18A 1.4200 . ?
C17A C22A 1.5095 . ?
C18A C19A 1.4200 . ?
C18A C23A 1.5095 . ?
C19A C20A 1.4200 . ?
C19A C24A 1.5095 . ?
C20A C25A 1.5095 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
C24A H24D 0.9600 . ?
C24A H24E 0.9600 . ?
C24A H24F 0.9600 . ?
C25A H25D 0.9600 . ?
C25A H25E 0.9600 . ?
C25A H25F 0.9600 . ?

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
N8 Ir1 I1 89.26(12) . . ?
N8 Ir1 N1 74.68(18) . . ?
N8 Ir1 C20 98.28(16) . . ?
N8 Ir1 C16 119.18(17) . . ?
N8 Ir1 C17 156.91(18) . . ?
N8 Ir1 C18 145.8(2) . . ?
N8 Ir1 C19 110.59(19) . . ?
N8 Ir1 C16A 120.0(3) . . ?
N8 Ir1 C17A 104.5(3) . . ?
N8 Ir1 C18A 123.5(3) . . ?
N8 Ir1 C19A 159.5(3) . . ?
N8 Ir1 C20A 154.7(3) . . ?
N1 Ir1 I1 86.84(11) . . ?
N1 Ir1 C20 126.55(16) . . ?
N1 Ir1 C16 99.98(15) . . ?
N1 Ir1 C17 105.85(17) . . ?
N1 Ir1 C18 139.4(2) . . ?
N1 Ir1 C19 161.63(16) . . ?
N1 Ir1 C16A 164.8(3) . . ?
N1 Ir1 C18A 106.2(3) . . ?
N1 Ir1 C19A 104.3(3) . . ?
N1 Ir1 C20A 130.0(3) . . ?
C20 Ir1 I1 146.61(12) . . ?
C20 Ir1 C19 36.64(6) . . ?
C16 Ir1 I1 151.57(12) . . ?
C16 Ir1 C20 37.13(6) . . ?
C16 Ir1 C18 62.52(10) . . ?
C16 Ir1 C19 61.86(9) . . ?
C17 Ir1 I1 113.82(13) . . ?
C17 Ir1 C20 62.33(9) . . ?
C17 Ir1 C16 37.74(7) . . ?
C17 Ir1 C18 37.56(8) . . ?
C17 Ir1 C19 62.14(10) . . ?
C18 Ir1 I1 94.47(13) . . ?
C18 Ir1 C20 61.76(9) . . ?
C18 Ir1 C19 36.87(6) . . ?
C19 Ir1 I1 110.43(14) . . ?
C16A Ir1 I1 96.7(3) . . ?
C16A Ir1 C19A 60.7(2) . . ?
C16A Ir1 C20A 36.08(16) . . ?
C17A Ir1 I1 134.3(3) . . ?
C17A Ir1 N1 138.7(4) . . ?
C17A Ir1 C16A 38.62(18) . . ?
C17A Ir1 C18A 39.0(2) . . ?
C17A Ir1 C19A 62.3(3) . . ?
C17A Ir1 C20A 62.0(3) . . ?
C18A Ir1 I1 146.7(3) . . ?
C18A Ir1 C16A 63.4(3) . . ?
C18A Ir1 C19A 36.46(18) . . ?
C18A Ir1 C20A 60.8(3) . . ?
C19A Ir1 I1 111.2(2) . . ?
C19A Ir1 C20A 35.18(16) . . ?
C20A Ir1 I1 87.2(3) . . ?
F14 P10 F13 174.8(8) . . ?
F14 P10 F16 92.0(7) . . ?
F15 P10 F14 90.1(7) . . ?
F15 P10 F13 88.1(7) . . ?
F15 P10 F16 177.7(6) . . ?
F15 P10 F12 91.5(10) . . ?
F11 P10 F14 98.1(9) . . ?
F11 P10 F13 86.8(8) . . ?
F11 P10 F15 90.5(8) . . ?
F11 P10 F16 88.2(8) . . ?
F11 P10 F12 176.9(10) . . ?
F16 P10 F13 90.0(6) . . ?
F12 P10 F14 84.3(7) . . ?
F12 P10 F13 90.9(8) . . ?
F12 P10 F16 89.7(9) . . ?
F13A P10 F16A 91.9(13) . . ?
F13A P10 F12A 89.9(15) . . ?
F13A P10 F14A 175.5(14) . . ?
F13A P10 F0AA 89.0(11) . . ?
F13A P10 F11A 90.3(12) . . ?
F16A P10 F14A 92.5(14) . . ?
F16A P10 F0AA 177.3(14) . . ?
F16A P10 F11A 91.5(13) . . ?
F12A P10 F16A 90.7(15) . . ?
F12A P10 F14A 89.3(14) . . ?
F12A P10 F0AA 91.8(14) . . ?
F12A P10 F11A 177.8(16) . . ?
F0AA P10 F14A 86.7(11) . . ?
F11A P10 F14A 90.3(13) . . ?
F11A P10 F0AA 86.0(11) . . ?
N7 N8 Ir1 121.6(4) . . ?
N7 N8 C9 112.5(4) . . ?
C9 N8 Ir1 125.8(3) . . ?
C12 O12 H12 109.5 . . ?
C6 N1 Ir1 113.4(3) . . ?
C2 N1 Ir1 128.8(3) . . ?
C2 N1 C6 117.8(4) . . ?
N8 N7 C6 111.9(4) . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C3 118.4(5) . . ?
C3 C4 H4 120.8 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.3(5) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 N7 118.3(4) . . ?
N1 C6 C5 122.9(5) . . ?
N7 C6 C5 118.7(5) . . ?
C4 C3 C15 117.5(5) . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 C15 121.5(5) . . ?
C10 C9 N8 119.9(5) . . ?
C14 C9 N8 119.2(5) . . ?
C14 C9 C10 120.9(5) . . ?
N1 C2 C3 121.6(5) . . ?
N1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
F15C C15 F15A 106.0(6) . . ?
F15C C15 C3 113.2(5) . . ?
F15B C15 F15C 107.9(7) . . ?
F15B C15 F15A 106.4(6) . . ?
F15B C15 C3 111.6(6) . . ?
F15A C15 C3 111.3(6) . . ?
O12 C12 C13 117.9(6) . . ?
O12 C12 C11 121.9(6) . . ?
C13 C12 C11 120.2(6) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C27 O26 H26 109.5 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(5) . . ?
C11 C10 H10 120.5 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.2(6) . . ?
C10 C11 H11 119.9 . . ?
C16 C20 Ir1 69.56(15) . . ?
C16 C20 C19 108.0 . . ?
C16 C20 C25 126.0 . . ?
C19 C20 Ir1 72.13(13) . . ?
C19 C20 C25 126.0 . . ?
C25 C20 Ir1 123.92(15) . . ?
C20 C16 Ir1 73.31(15) . . ?
C20 C16 C17 108.0 . . ?
C20 C16 C21 126.0 . . ?
C17 C16 Ir1 70.41(16) . . ?
C17 C16 C21 126.0 . . ?
C21 C16 Ir1 121.97(13) . . ?
C16 C17 Ir1 71.84(14) . . ?
C16 C17 C22 126.0 . . ?
C18 C17 Ir1 72.67(14) . . ?
C18 C17 C16 108.0 . . ?
C18 C17 C22 126.0 . . ?
C22 C17 Ir1 121.23(14) . . ?
C17 C18 Ir1 69.77(14) . . ?
C17 C18 C23 126.0 . . ?
C19 C18 Ir1 73.15(16) . . ?
C19 C18 C17 108.0 . . ?
C19 C18 C23 126.0 . . ?
C23 C18 Ir1 122.74(12) . . ?
C20 C19 Ir1 71.24(13) . . ?
C20 C19 C24 126.0 . . ?
C18 C19 Ir1 69.98(16) . . ?
C18 C19 C20 108.0 . . ?
C18 C19 C24 126.0 . . ?
C24 C19 Ir1 124.39(14) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
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 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 C14 H14 120.3 . . ?
C13 C14 C9 119.5(6) . . ?
C13 C14 H14 120.3 . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17A C16A Ir1 66.0(4) . . ?
C17A C16A C20A 108.0 . . ?
C17A C16A C21A 126.0 . . ?
C20A C16A Ir1 78.0(4) . . ?
C20A C16A C21A 126.0 . . ?
C21A C16A Ir1 121.5(4) . . ?
C16A C17A Ir1 75.4(4) . . ?
C16A C17A C22A 126.0 . . ?
C18A C17A Ir1 74.0(4) . . ?
C18A C17A C16A 108.0 . . ?
C18A C17A C22A 126.0 . . ?
C22A C17A Ir1 116.7(4) . . ?
C17A C18A Ir1 67.0(4) . . ?
C17A C18A C19A 108.0 . . ?
C17A C18A C23A 126.0 . . ?
C19A C18A Ir1 78.3(4) . . ?
C19A C18A C23A 126.0 . . ?
C23A C18A Ir1 120.3(3) . . ?
C18A C19A Ir1 65.2(4) . . ?
C18A C19A C20A 108.0 . . ?
C18A C19A C24A 126.0 . . ?
C20A C19A Ir1 73.1(3) . . ?
C20A C19A C24A 126.0 . . ?
C24A C19A Ir1 127.1(3) . . ?
C16A C20A Ir1 65.9(4) . . ?
C16A C20A C25A 126.0 . . ?
C19A C20A Ir1 71.7(4) . . ?
C19A C20A C16A 108.0 . . ?
C19A C20A C25A 126.0 . . ?
C25A C20A Ir1 127.9(4) . . ?
C16A C21A H21D 109.5 . . ?
C16A C21A H21E 109.5 . . ?
C16A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C17A C22A H22D 109.5 . . ?
C17A C22A H22E 109.5 . . ?
C17A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C18A C23A H23D 109.5 . . ?
C18A C23A H23E 109.5 . . ?
C18A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C19A C24A H24D 109.5 . . ?
C19A C24A H24E 109.5 . . ?
C19A C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
C20A C25A H25D 109.5 . . ?
C20A C25A H25E 109.5 . . ?
C20A C25A H25F 109.5 . . ?
H25D C25A H25E 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?

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
_geom_hbond_publ_flag
O12 H12 O26 0.82 1.85 2.659(9) 168.8 . yes
O26 H26 F12 0.82 2.48 3.29(2) 171.0 2_655 yes
O26 H26 F12A 0.82 2.39 3.10(4) 145.1 2_655 yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 6.020
_oxdiff_exptl_absorpt_empirical_full_min 0.516
####################################################################### 
# 
# 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_wz3
_database_code_depnum_ccdc_archive 'CCDC 1860997'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2018-08-08 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2017-08-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 I Ir N3, I'
_chemical_formula_sum            'C26 H26 I2 Ir N3'
_chemical_formula_weight         826.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 F6 P I Ir'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.19420(10)
_cell_length_b                   8.21580(10)
_cell_length_c                   33.7933(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.7830(10)
_cell_angle_gamma                90
_cell_volume                     2539.68(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28319
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4240
_cell_measurement_theta_min      4.8160
_shelx_estimated_absorpt_T_max   0.591
_shelx_estimated_absorpt_T_min   0.067
_exptl_absorpt_coefficient_mu    29.401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            43995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.554
_diffrn_reflns_theta_min         4.834
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -16.00   1.00    1.00    --  -42.36 -57.00-180.00   97
  2  ω   -115.00 -20.00   1.00    1.00    --  -42.36 -37.00 -30.00   95
  3  ω    -96.00  -2.00   1.00    1.00    --  -42.36 125.00 -30.00   94
  4  ω      1.00  82.00   1.00    1.00    --   42.36 -99.00-150.00   81
  5  ω     82.00 178.00   1.00    4.00    --  106.00  30.00  30.00   96
  6  ω     34.00 121.00   1.00    4.00    --  106.00-125.00 -90.00   87
  7  ω     25.00 109.00   1.00    4.00    --  106.00 -94.00  30.00   84
  8  ω     32.00 137.00   1.00    4.00    --  106.00 -77.00  90.00  105
  9  ω     31.00 130.00   1.00    4.00    --  106.00 -30.00   0.00   99
 10  ω     82.00 178.00   1.00    4.00    --  106.00  30.00-180.00   96
 11  ω     31.00 130.00   1.00    4.00    --  106.00 -30.00-150.00   99
 12  ω     31.00 130.00   1.00    4.00    --  106.00 -30.00  90.00   99
 13  ω     32.00 137.00   1.00    4.00    --  106.00 -77.00-120.00  105
 14  ω   -113.00 -16.00   1.00    1.00    --  -42.36 -57.00 -90.00   97
 15  ω    -65.00  31.00   1.00    1.00    --  -42.36  37.00 -30.00   96
 16  ω   -113.00 -16.00   1.00    1.00    --  -42.36 -57.00  90.00   97
 17  ω   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00  30.00  105
 18  ω     78.00 176.00   1.00    4.00    --  106.00  61.00-180.00   98
 19  ω     78.00 176.00   1.00    4.00    --  106.00  61.00 -30.00   98
 20  ω     82.00 177.00   1.00    4.00    --  106.00  45.00  90.00   95
 21  ω     75.00 178.00   1.00    4.00    --  106.00  77.00  30.00  103
 22  ω     61.00 178.00   1.00    4.00    --  106.00  15.00 -60.00  117
 23  ω     75.00 178.00   1.00    4.00    --  106.00  77.00 -90.00  103
 24  ω     78.00 176.00   1.00    4.00    --  106.00  61.00-150.00   98
 25  ω     78.00 176.00   1.00    4.00    --  106.00  61.00 120.00   98
 26  ω   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00  90.00  105
 27  ω   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00 -60.00  105
 28  ω      1.00  82.00   1.00    1.00    --   42.36 -99.00 120.00   81
 29  ω     11.00 116.00   1.00    1.00    --   42.36  77.00-150.00  105
 30  ω     75.00 178.00   1.00    4.00    --  106.00  77.00   0.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0157583000
_diffrn_orient_matrix_UB_12      -0.1565496000
_diffrn_orient_matrix_UB_13      -0.0251490000
_diffrn_orient_matrix_UB_21      -0.0604828000
_diffrn_orient_matrix_UB_22      0.1006682000
_diffrn_orient_matrix_UB_23      -0.0364798000
_diffrn_orient_matrix_UB_31      0.1563379000
_diffrn_orient_matrix_UB_32      0.0231431000
_diffrn_orient_matrix_UB_33      -0.0116793000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5010
_reflns_number_total             5081
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         1.259
_refine_diff_density_min         -1.291
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0255
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+5.2482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0613
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C11(H11), C18(H18), C5(H5), C4(H4), C10(H10), C19(H19),
 C14(H14), C15(H15), C13(H13), C16(H16), C17(H17), C12(H12)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C27(H27A,H27B,H27C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.62741(2) 0.57851(2) 0.62614(2) 0.01190(6) Uani 1 1 d . . . . .
I1 I 0.51079(3) 0.74158(3) 0.68449(2) 0.02277(7) Uani 1 1 d . . . . .
I2 I 0.18779(3) 0.27012(3) 0.50747(2) 0.02457(8) Uani 1 1 d . . . . .
N8 N 0.7054(4) 0.7978(4) 0.60714(9) 0.0148(6) Uani 1 1 d . . . . .
N7 N 0.6266(4) 0.8859(4) 0.58224(10) 0.0174(7) Uani 1 1 d . . . . .
N1 N 0.4595(4) 0.6736(4) 0.58773(9) 0.0146(6) Uani 1 1 d . . . . .
C20 C 0.9243(5) 0.4385(5) 0.68545(11) 0.0170(8) Uani 1 1 d . . . . .
C21 C 0.7986(4) 0.4158(5) 0.65467(11) 0.0158(7) Uani 1 1 d . . . . .
C25 C 0.8056(4) 0.4187(4) 0.61217(11) 0.0149(7) Uani 1 1 d . . . . .
C2 C 0.3259(4) 0.6085(5) 0.57751(12) 0.0177(8) Uani 1 1 d . . . . .
H2 H 0.3017 0.5076 0.5889 0.021 Uiso 1 1 calc R . . . .
C9 C 0.8493(4) 0.8607(5) 0.61763(11) 0.0163(7) Uani 1 1 d . . . . .
C24 C 0.6681(4) 0.3589(5) 0.59314(11) 0.0152(7) Uani 1 1 d . . . . .
C6 C 0.4910(4) 0.8187(5) 0.57111(11) 0.0162(8) Uani 1 1 d . . . . .
C3 C 0.2237(5) 0.6841(5) 0.55099(12) 0.0200(8) Uani 1 1 d . . . . .
H3 H 0.1314 0.6344 0.5440 0.024 Uiso 1 1 calc R . . . .
C11 C 1.0644(5) 0.8668(5) 0.66428(13) 0.0248(9) Uani 1 1 d . . . . .
H11 H 1.1148 0.8360 0.6891 0.030 Uiso 1 1 calc R . . . .
C18 C 1.0329(5) 0.5361(6) 0.74885(13) 0.0276(10) Uani 1 1 d . . . . .
H18 H 1.0246 0.5965 0.7725 0.033 Uiso 1 1 calc R . . . .
C23 C 0.5769(4) 0.3170(4) 0.62423(11) 0.0147(7) Uani 1 1 d . . . . .
C5 C 0.3911(5) 0.9015(5) 0.54468(12) 0.0202(8) Uani 1 1 d . . . . .
H5 H 0.4156 1.0033 0.5338 0.024 Uiso 1 1 calc R . . . .
C4 C 0.2558(5) 0.8323(5) 0.53463(11) 0.0185(8) Uani 1 1 d . . . . .
H4 H 0.1855 0.8859 0.5167 0.022 Uiso 1 1 calc R . . . .
C22 C 0.6587(4) 0.3487(5) 0.66190(11) 0.0160(8) Uani 1 1 d . . . . .
C10 C 0.9198(5) 0.8188(5) 0.65441(12) 0.0196(8) Uani 1 1 d . . . . .
H10 H 0.8700 0.7579 0.6728 0.023 Uiso 1 1 calc R . . . .
C19 C 0.9132(5) 0.5232(5) 0.72046(12) 0.0225(9) Uani 1 1 d . . . . .
H19 H 0.8231 0.5728 0.7251 0.027 Uiso 1 1 calc R . . . .
C14 C 0.9174(5) 0.9572(5) 0.59110(12) 0.0200(8) Uani 1 1 d . . . . .
H14 H 0.8671 0.9880 0.5663 0.024 Uiso 1 1 calc R . . . .
C15 C 1.0568(5) 0.3624(6) 0.67972(12) 0.0238(9) Uani 1 1 d . . . . .
H15 H 1.0658 0.3028 0.6560 0.029 Uiso 1 1 calc R . . . .
C28 C 0.4327(5) 0.2329(5) 0.61920(12) 0.0205(8) Uani 1 1 d . . . . .
H28A H 0.3660 0.2848 0.6362 0.031 Uiso 1 1 calc GR . . . .
H28B H 0.4456 0.1182 0.6267 0.031 Uiso 1 1 calc GR . . . .
H28C H 0.3916 0.2403 0.5914 0.031 Uiso 1 1 calc GR . . . .
C13 C 1.0602(5) 1.0076(5) 0.60152(14) 0.0241(9) Uani 1 1 d . . . . .
H13 H 1.1079 1.0749 0.5839 0.029 Uiso 1 1 calc R . . . .
C16 C 1.1748(5) 0.3736(6) 0.70850(15) 0.0317(10) Uani 1 1 d . . . . .
H16 H 1.2639 0.3203 0.7046 0.038 Uiso 1 1 calc R . . . .
C29 C 0.6081(5) 0.3076(6) 0.70128(12) 0.0220(9) Uani 1 1 d . . . . .
H29A H 0.6916 0.3092 0.7217 0.033 Uiso 1 1 calc GR . . . .
H29B H 0.5640 0.1989 0.7000 0.033 Uiso 1 1 calc GR . . . .
H29C H 0.5354 0.3877 0.7079 0.033 Uiso 1 1 calc GR . . . .
C17 C 1.1637(5) 0.4621(6) 0.74300(14) 0.0312(10) Uani 1 1 d . . . . .
H17 H 1.2454 0.4717 0.7624 0.037 Uiso 1 1 calc R . . . .
C12 C 1.1340(5) 0.9595(5) 0.63773(14) 0.0240(9) Uani 1 1 d . . . . .
H12 H 1.2330 0.9909 0.6442 0.029 Uiso 1 1 calc R . . . .
C27 C 0.6307(5) 0.3337(5) 0.54952(11) 0.0214(8) Uani 1 1 d . . . . .
H27A H 0.5251 0.3472 0.5429 0.032 Uiso 1 1 calc GR . . . .
H27B H 0.6593 0.2236 0.5423 0.032 Uiso 1 1 calc GR . . . .
H27C H 0.6830 0.4136 0.5348 0.032 Uiso 1 1 calc GR . . . .
C26 C 0.9309(5) 0.4706(5) 0.59052(12) 0.0199(8) Uani 1 1 d . . . . .
H26A H 0.8943 0.5296 0.5663 0.030 Uiso 1 1 calc GR . . . .
H26B H 0.9856 0.3744 0.5833 0.030 Uiso 1 1 calc GR . . . .
H26C H 0.9955 0.5418 0.6076 0.030 Uiso 1 1 calc GR . . . .


_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 I1 2.6943(3) . ?
Ir1 N8 2.065(3) . ?
Ir1 N1 2.068(3) . ?
Ir1 C21 2.211(4) . ?
Ir1 C25 2.188(4) . ?
Ir1 C24 2.173(4) . ?
Ir1 C23 2.198(4) . ?
Ir1 C22 2.244(4) . ?
N8 N7 1.278(5) . ?
N8 C9 1.432(5) . ?
N7 C6 1.381(5) . ?
N1 C2 1.352(5) . ?
N1 C6 1.361(5) . ?
C20 C21 1.487(5) . ?
C20 C19 1.385(6) . ?
C20 C15 1.400(6) . ?
C21 C25 1.444(5) . ?
C21 C22 1.443(6) . ?
C25 C24 1.446(5) . ?
C25 C26 1.488(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(6) . ?
C9 C10 1.386(6) . ?
C9 C14 1.392(6) . ?
C24 C23 1.450(5) . ?
C24 C27 1.494(5) . ?
C6 C5 1.393(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.394(6) . ?
C11 C12 1.382(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(6) . ?
C18 C17 1.380(7) . ?
C23 C22 1.436(5) . ?
C23 C28 1.490(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.379(6) . ?
C4 H4 0.9500 . ?
C22 C29 1.492(5) . ?
C10 H10 0.9500 . ?
C19 H19 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.388(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(6) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C12 1.395(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(7) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C17 H17 0.9500 . ?
C12 H12 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
N8 Ir1 I1 88.28(9) . . ?
N8 Ir1 N1 74.69(13) . . ?
N8 Ir1 C21 114.14(14) . . ?
N8 Ir1 C25 99.52(14) . . ?
N8 Ir1 C24 118.80(14) . . ?
N8 Ir1 C23 157.32(13) . . ?
N8 Ir1 C22 150.65(14) . . ?
N1 Ir1 I1 86.81(9) . . ?
N1 Ir1 C21 162.94(13) . . ?
N1 Ir1 C25 128.28(13) . . ?
N1 Ir1 C24 98.51(13) . . ?
N1 Ir1 C23 102.05(13) . . ?
N1 Ir1 C22 134.66(14) . . ?
C21 Ir1 I1 107.44(10) . . ?
C21 Ir1 C22 37.79(15) . . ?
C25 Ir1 I1 144.91(10) . . ?
C25 Ir1 C21 38.34(14) . . ?
C25 Ir1 C23 64.39(14) . . ?
C25 Ir1 C22 63.48(14) . . ?
C24 Ir1 I1 152.89(10) . . ?
C24 Ir1 C21 64.53(14) . . ?
C24 Ir1 C25 38.72(14) . . ?
C24 Ir1 C23 38.74(14) . . ?
C24 Ir1 C22 63.81(14) . . ?
C23 Ir1 I1 114.15(10) . . ?
C23 Ir1 C21 63.94(14) . . ?
C23 Ir1 C22 37.69(14) . . ?
C22 Ir1 I1 93.60(10) . . ?
N7 N8 Ir1 120.5(3) . . ?
N7 N8 C9 114.0(3) . . ?
C9 N8 Ir1 125.4(3) . . ?
N8 N7 C6 112.9(3) . . ?
C2 N1 Ir1 127.7(3) . . ?
C2 N1 C6 117.9(3) . . ?
C6 N1 Ir1 114.4(3) . . ?
C19 C20 C21 122.8(4) . . ?
C19 C20 C15 118.9(4) . . ?
C15 C20 C21 118.2(4) . . ?
C20 C21 Ir1 134.3(3) . . ?
C25 C21 Ir1 70.0(2) . . ?
C25 C21 C20 125.7(4) . . ?
C22 C21 Ir1 72.4(2) . . ?
C22 C21 C20 125.0(3) . . ?
C22 C21 C25 107.7(3) . . ?
C21 C25 Ir1 71.7(2) . . ?
C21 C25 C24 108.2(3) . . ?
C21 C25 C26 127.5(4) . . ?
C24 C25 Ir1 70.1(2) . . ?
C24 C25 C26 124.4(3) . . ?
C26 C25 Ir1 124.6(3) . . ?
N1 C2 H2 119.0 . . ?
N1 C2 C3 121.9(4) . . ?
C3 C2 H2 119.0 . . ?
C10 C9 N8 118.0(4) . . ?
C10 C9 C14 121.3(4) . . ?
C14 C9 N8 120.7(4) . . ?
C25 C24 Ir1 71.2(2) . . ?
C25 C24 C23 107.6(3) . . ?
C25 C24 C27 126.2(4) . . ?
C23 C24 Ir1 71.5(2) . . ?
C23 C24 C27 126.1(4) . . ?
C27 C24 Ir1 125.9(3) . . ?
N7 C6 C5 119.9(4) . . ?
N1 C6 N7 117.5(3) . . ?
N1 C6 C5 122.6(4) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C12 C11 C10 119.6(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(4) . . ?
C24 C23 Ir1 69.7(2) . . ?
C24 C23 C28 126.9(3) . . ?
C22 C23 Ir1 72.9(2) . . ?
C22 C23 C24 108.1(3) . . ?
C22 C23 C28 124.5(4) . . ?
C28 C23 Ir1 129.8(3) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5 120.8 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
C21 C22 Ir1 69.8(2) . . ?
C21 C22 C29 126.9(4) . . ?
C23 C22 Ir1 69.4(2) . . ?
C23 C22 C21 108.4(3) . . ?
C23 C22 C29 124.6(4) . . ?
C29 C22 Ir1 129.5(3) . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C9 C14 H14 120.6 . . ?
C13 C14 C9 118.8(4) . . ?
C13 C14 H14 120.6 . . ?
C20 C15 H15 119.9 . . ?
C16 C15 C20 120.3(4) . . ?
C16 C15 H15 119.9 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C14 C13 H13 119.9 . . ?
C14 C13 C12 120.1(4) . . ?
C12 C13 H13 119.9 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(5) . . ?
C17 C16 H16 119.8 . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.914
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_wz9
_database_code_depnum_ccdc_archive 'CCDC 1860996'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2018-08-08 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2018-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 I Ir N3, I'
_chemical_formula_sum            'C21 H24 I2 Ir N3'
_chemical_formula_weight         764.43
_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'
I I -0.4742 1.8119 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.7681(4)
_cell_length_b                   8.70230(10)
_cell_length_c                   16.6407(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.9350(10)
_cell_angle_gamma                90
_cell_volume                     4583.36(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    33751
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.8600
_cell_measurement_theta_min      2.5741
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    2.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37770
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.213
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  64.00   1.00   42.50    --  -11.99  77.00 150.00  109
  2  ω    -45.00  64.00   1.00   42.50    --  -11.99  77.00   0.00  109
  3  ω    -20.00  89.00   1.00   42.50    --   13.09  77.00  30.00  109
  4  ω    -20.00  89.00   1.00   42.50    --   13.09  77.00 -90.00  109
  5  ω    -86.00  10.00   1.00   42.50    --  -11.99 -37.00  60.00   96
  6  ω    -20.00  54.00   1.00   42.50    --   13.09 -99.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0077496000
_diffrn_orient_matrix_UB_12      -0.0761946000
_diffrn_orient_matrix_UB_13      0.0046433000
_diffrn_orient_matrix_UB_21      0.0208243000
_diffrn_orient_matrix_UB_22      0.0267321000
_diffrn_orient_matrix_UB_23      -0.0038854000
_diffrn_orient_matrix_UB_31      0.0030139000
_diffrn_orient_matrix_UB_32      0.0108431000
_diffrn_orient_matrix_UB_33      0.0423478000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5601
_reflns_number_total             6241
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.01
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         1.771
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         6241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0199
_refine_ls_restrained_S_all      1.057
_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)+(0.0157P)²+10.6445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0401
_refine_ls_wR_factor_ref         0.0420
_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
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C4(H4), C2(H2), C5(H5), C14(H14), C11(H11), C13(H13),
 C12(H12)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.38630(2) 0.61726(2) 0.45560(2) 0.02114(3) Uani 1 1 d . . . . .
I1 I 0.43781(2) 0.52291(3) 0.58239(2) 0.03982(6) Uani 1 1 d . . . . .
I2 I 0.23190(2) 0.51160(2) 0.33400(2) 0.04582(6) Uani 1 1 d . . . . .
N8 N 0.37288(7) 0.3939(2) 0.42393(13) 0.0252(5) Uani 1 1 d . . . . .
N1 N 0.33800(7) 0.5527(3) 0.52392(13) 0.0246(5) Uani 1 1 d . . . . .
N7 N 0.34329(7) 0.3210(3) 0.45385(14) 0.0285(5) Uani 1 1 d . . . . .
C6 C 0.32420(9) 0.4064(3) 0.51123(17) 0.0271(6) Uani 1 1 d . . . . .
C17 C 0.39353(9) 0.8656(3) 0.45895(17) 0.0287(6) Uani 1 1 d . . . . .
C9 C 0.39351(9) 0.3029(3) 0.36668(16) 0.0279(6) Uani 1 1 d . . . . .
C15 C 0.41775(9) 0.7199(3) 0.35549(16) 0.0272(6) Uani 1 1 d . . . . .
C19 C 0.37240(9) 0.7340(3) 0.34071(16) 0.0281(6) Uani 1 1 d . . . . .
C3 C 0.29179(9) 0.5713(4) 0.62847(18) 0.0338(6) Uani 1 1 d . . . . .
H3 H 0.280515 0.631576 0.669110 0.041 Uiso 1 1 calc R . . . .
C16 C 0.43038(9) 0.8026(3) 0.42704(17) 0.0274(6) Uani 1 1 d . . . . .
C10 C 0.43723(10) 0.3033(4) 0.37101(18) 0.0346(6) Uani 1 1 d . . . . .
H10 H 0.453170 0.368006 0.408174 0.042 Uiso 1 1 calc R . . . .
C4 C 0.27846(9) 0.4218(4) 0.61588(18) 0.0325(6) Uani 1 1 d . . . . .
H4 H 0.258436 0.377466 0.648244 0.039 Uiso 1 1 calc R . . . .
C24 C 0.44671(11) 0.6511(4) 0.29885(19) 0.0401(7) Uani 1 1 d . . . . .
H24A H 0.472628 0.615602 0.329449 0.060 Uiso 1 1 calc GR . . . .
H24B H 0.453801 0.728772 0.259546 0.060 Uiso 1 1 calc GR . . . .
H24C H 0.432669 0.563997 0.270501 0.060 Uiso 1 1 calc GR . . . .
C2 C 0.32146(9) 0.6334(3) 0.58216(17) 0.0309(6) Uani 1 1 d . . . . .
H2 H 0.330439 0.736419 0.591786 0.037 Uiso 1 1 calc R . . . .
C5 C 0.29467(9) 0.3379(3) 0.55563(17) 0.0306(6) Uani 1 1 d . . . . .
H5 H 0.285733 0.235193 0.544865 0.037 Uiso 1 1 calc R . . . .
C18 C 0.35765(9) 0.8261(3) 0.40412(17) 0.0288(6) Uani 1 1 d . . . . .
C22 C 0.39366(12) 0.9706(4) 0.5306(2) 0.0443(8) Uani 1 1 d . . . . .
H22A H 0.364965 0.978532 0.547606 0.066 Uiso 1 1 calc GR . . . .
H22B H 0.403505 1.072758 0.515891 0.066 Uiso 1 1 calc GR . . . .
H22C H 0.412580 0.929169 0.574933 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.36953(11) 0.2127(4) 0.31125(18) 0.0374(7) Uani 1 1 d . . . . .
H14 H 0.339544 0.215309 0.308412 0.045 Uiso 1 1 calc R . . . .
C11 C 0.45731(11) 0.2066(4) 0.3196(2) 0.0446(8) Uani 1 1 d . . . . .
H11 H 0.487290 0.203658 0.322258 0.054 Uiso 1 1 calc R . . . .
C13 C 0.39019(13) 0.1188(4) 0.2602(2) 0.0459(8) Uani 1 1 d . . . . .
H13 H 0.374324 0.056678 0.221611 0.055 Uiso 1 1 calc R . . . .
C23 C 0.47512(10) 0.8265(4) 0.4600(2) 0.0431(8) Uani 1 1 d . . . . .
H23A H 0.476048 0.846535 0.518032 0.065 Uiso 1 1 calc GR . . . .
H23B H 0.487034 0.914431 0.432938 0.065 Uiso 1 1 calc GR . . . .
H23C H 0.491656 0.734145 0.450504 0.065 Uiso 1 1 calc GR . . . .
C20 C 0.34644(10) 0.6731(4) 0.26895(18) 0.0408(7) Uani 1 1 d . . . . .
H20A H 0.359777 0.580319 0.249459 0.061 Uiso 1 1 calc GR . . . .
H20B H 0.344390 0.750964 0.226232 0.061 Uiso 1 1 calc GR . . . .
H20C H 0.318081 0.648001 0.283923 0.061 Uiso 1 1 calc GR . . . .
C21 C 0.31289(10) 0.8749(4) 0.4099(2) 0.0424(8) Uani 1 1 d . . . . .
H21A H 0.293863 0.790457 0.392275 0.064 Uiso 1 1 calc GR . . . .
H21B H 0.306660 0.964595 0.375319 0.064 Uiso 1 1 calc GR . . . .
H21C H 0.308790 0.901538 0.465917 0.064 Uiso 1 1 calc GR . . . .
C12 C 0.43385(13) 0.1153(4) 0.2651(2) 0.0484(9) Uani 1 1 d . . . . .
H12 H 0.447797 0.049168 0.230524 0.058 Uiso 1 1 calc R . . . .


_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 I1 2.6851(2) . ?
Ir1 N8 2.049(2) . ?
Ir1 N1 2.065(2) . ?
Ir1 C17 2.174(3) . ?
Ir1 C15 2.204(3) . ?
Ir1 C19 2.177(3) . ?
Ir1 C16 2.214(3) . ?
Ir1 C18 2.175(3) . ?
N8 N7 1.270(3) . ?
N8 C9 1.439(3) . ?
N1 C6 1.357(4) . ?
N1 C2 1.340(4) . ?
N7 C6 1.390(4) . ?
C6 C5 1.379(4) . ?
C17 C16 1.435(4) . ?
C17 C18 1.439(4) . ?
C17 C22 1.501(4) . ?
C9 C10 1.385(4) . ?
C9 C14 1.388(4) . ?
C15 C19 1.446(4) . ?
C15 C16 1.419(4) . ?
C15 C24 1.498(4) . ?
C19 C18 1.435(4) . ?
C19 C20 1.489(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(4) . ?
C3 C2 1.378(4) . ?
C16 C23 1.493(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C2 H2 0.9500 . ?
C5 H5 0.9500 . ?
C18 C21 1.495(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C13 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.383(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 . ?
C12 H12 0.9500 . ?

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
N8 Ir1 I1 90.65(6) . . ?
N8 Ir1 N1 74.66(9) . . ?
N8 Ir1 C17 165.69(10) . . ?
N8 Ir1 C15 106.74(10) . . ?
N8 Ir1 C19 101.24(10) . . ?
N8 Ir1 C16 139.22(10) . . ?
N8 Ir1 C18 128.35(10) . . ?
N1 Ir1 I1 85.16(6) . . ?
N1 Ir1 C17 109.78(10) . . ?
N1 Ir1 C15 158.94(9) . . ?
N1 Ir1 C19 120.43(9) . . ?
N1 Ir1 C16 146.11(10) . . ?
N1 Ir1 C18 97.97(10) . . ?
C17 Ir1 I1 103.18(7) . . ?
C17 Ir1 C15 64.06(10) . . ?
C17 Ir1 C19 64.62(10) . . ?
C17 Ir1 C16 38.17(10) . . ?
C17 Ir1 C18 38.65(10) . . ?
C15 Ir1 I1 115.63(7) . . ?
C15 Ir1 C16 37.47(10) . . ?
C19 Ir1 I1 153.74(7) . . ?
C19 Ir1 C15 38.53(10) . . ?
C19 Ir1 C16 63.62(10) . . ?
C16 Ir1 I1 92.15(7) . . ?
C18 Ir1 I1 140.45(8) . . ?
C18 Ir1 C15 64.22(11) . . ?
C18 Ir1 C19 38.52(11) . . ?
C18 Ir1 C16 63.75(10) . . ?
N7 N8 Ir1 121.15(18) . . ?
N7 N8 C9 112.3(2) . . ?
C9 N8 Ir1 126.56(17) . . ?
C6 N1 Ir1 114.53(18) . . ?
C2 N1 Ir1 127.71(19) . . ?
C2 N1 C6 117.6(2) . . ?
N8 N7 C6 112.5(2) . . ?
N1 C6 N7 117.0(2) . . ?
N1 C6 C5 123.2(3) . . ?
C5 C6 N7 119.6(3) . . ?
C16 C17 Ir1 72.44(15) . . ?
C16 C17 C18 107.5(2) . . ?
C16 C17 C22 125.4(3) . . ?
C18 C17 Ir1 70.73(15) . . ?
C18 C17 C22 126.6(3) . . ?
C22 C17 Ir1 128.2(2) . . ?
C10 C9 N8 118.4(2) . . ?
C10 C9 C14 121.8(3) . . ?
C14 C9 N8 119.7(3) . . ?
C19 C15 Ir1 69.71(14) . . ?
C19 C15 C24 125.7(3) . . ?
C16 C15 Ir1 71.65(15) . . ?
C16 C15 C19 107.8(2) . . ?
C16 C15 C24 125.9(3) . . ?
C24 C15 Ir1 131.0(2) . . ?
C15 C19 Ir1 71.76(14) . . ?
C15 C19 C20 125.5(3) . . ?
C18 C19 Ir1 70.69(15) . . ?
C18 C19 C15 107.8(2) . . ?
C18 C19 C20 126.5(3) . . ?
C20 C19 Ir1 126.5(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(3) . . ?
C17 C16 Ir1 69.39(15) . . ?
C17 C16 C23 126.3(3) . . ?
C15 C16 Ir1 70.88(15) . . ?
C15 C16 C17 108.9(2) . . ?
C15 C16 C23 124.7(3) . . ?
C23 C16 Ir1 128.5(2) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.5(3) . . ?
C11 C10 H10 120.8 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C2 C3 121.9(3) . . ?
N1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 H5 120.8 . . ?
C17 C18 Ir1 70.62(15) . . ?
C17 C18 C21 126.7(3) . . ?
C19 C18 Ir1 70.80(15) . . ?
C19 C18 C17 108.0(2) . . ?
C19 C18 C21 125.3(3) . . ?
C21 C18 Ir1 125.4(2) . . ?
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 . . ?
C9 C14 H14 120.7 . . ?
C13 C14 C9 118.7(3) . . ?
C13 C14 H14 120.7 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.792
_oxdiff_exptl_absorpt_empirical_full_min 0.664
####################################################################### 
# 
# 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_gh2
_database_code_depnum_ccdc_archive 'CCDC 1921724'
loop_
_audit_author_name
_audit_author_address
'Guy J. Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-06-08 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2015-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23.5 Cl Ir N3 O, C H4 O, 0.5(Cl)'
_chemical_formula_sum            'C22 H27.50 Cl1.50 Ir N3 O2'
_chemical_formula_weight         611.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 F6 P Ir'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.93939(15)
_cell_length_b                   18.6768(3)
_cell_length_c                   13.4520(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.0660(14)
_cell_angle_gamma                90
_cell_volume                     2240.28(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18491
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.5290
_cell_measurement_theta_min      3.0350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1196
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36123
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.691
_diffrn_reflns_theta_min         2.531
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -10.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2951   57.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
  2 omega  -56.00   43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2951  -38.0000  -90.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2951   38.0000  150.0000 99

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2326  -99.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2951   38.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2951  -99.0000  120.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0434787000
_diffrn_orient_matrix_UB_12      -0.0302119000
_diffrn_orient_matrix_UB_13      0.0158484000
_diffrn_orient_matrix_UB_21      -0.0566151000
_diffrn_orient_matrix_UB_22      -0.0230046000
_diffrn_orient_matrix_UB_23      -0.0214026000
_diffrn_orient_matrix_UB_31      0.0350953000
_diffrn_orient_matrix_UB_32      0.0002983000
_diffrn_orient_matrix_UB_33      -0.0456684000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6752
_reflns_number_total             7716
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.581
_refine_diff_density_min         -2.963
_refine_diff_density_rms         0.685
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.297
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         7716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.297
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          ?
_olex2_refinement_description    
;
The asymmetric unit contains the Ir complex and a molecule of methanol and a chloride counter ion. 
The chloride counter ion sits on an inversion centre (so is at half occupancy)
Four times all this in the unit cell.
The OHs on the methanol and the phenol were not located but placed at calculated positions.
The problem is that there is only half a chloride counter ion per Ir complex and the phenol 
OH forms a hydrogen bond to a symmetry related phenol, so there is a clash of the OH hydrogens
This is because there is only one proton shared between the two phenol oxygens. 
In reality the hydrogen shuttles between the phenol oxygen O12 and the symmetry related O12 
but this situation cant be resolved by this Xray experiment. 
This was modelled by simply having H12 at 50% occupancy giving a total of one fully occupied
hydrogen (2 x half occupied H12) lying between O12 and its symmetry equivalent.

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) groups
2. Others
 Fixed Sof: H12(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
3.c Idealised tetrahedral OH refined as rotating group:
 O12(H12), O25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.35705(2) 0.72914(2) 0.51006(2) 0.01051(5) Uani 1 1 d . . . . .
Cl1 Cl 0.42017(10) 0.67935(5) 0.67117(6) 0.01979(18) Uani 1 1 d . . . . .
N1 N 0.4143(3) 0.63172(16) 0.4510(2) 0.0133(5) Uani 1 1 d . . . . .
C2 C 0.3270(4) 0.5736(2) 0.4401(3) 0.0184(7) Uani 1 1 d . . . . .
H2 H 0.2311 0.5740 0.4664 0.022 Uiso 1 1 calc R . . . .
C3 C 0.3733(5) 0.5129(2) 0.3914(3) 0.0225(8) Uani 1 1 d . . . . .
H3 H 0.3081 0.4728 0.3830 0.027 Uiso 1 1 calc R . . . .
C4 C 0.5144(5) 0.5105(2) 0.3549(3) 0.0233(8) Uani 1 1 d . . . . .
H4 H 0.5460 0.4696 0.3199 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6091(4) 0.5693(2) 0.3706(3) 0.0209(7) Uani 1 1 d . . . . .
H5 H 0.7083 0.5685 0.3496 0.025 Uiso 1 1 calc R . . . .
C6 C 0.5548(4) 0.62936(19) 0.4180(2) 0.0150(6) Uani 1 1 d . . . . .
N7 N 0.6462(3) 0.68875(17) 0.4352(2) 0.0162(6) Uani 1 1 d . . . . .
N8 N 0.5821(4) 0.73868(16) 0.4824(2) 0.0135(6) Uani 1 1 d . . . . .
C9 C 0.6712(4) 0.8001(2) 0.5015(2) 0.0143(6) Uani 1 1 d . . . . .
C10 C 0.7789(4) 0.8209(2) 0.4369(3) 0.0187(7) Uani 1 1 d . . . . .
H10 H 0.7922 0.7940 0.3782 0.022 Uiso 1 1 calc R . . . .
C11 C 0.8649(4) 0.8800(2) 0.4585(3) 0.0203(7) Uani 1 1 d . . . . .
H11 H 0.9364 0.8945 0.4135 0.024 Uiso 1 1 calc R . . . .
O12 O 0.9307(3) 0.97732(16) 0.5696(2) 0.0289(7) Uani 1 1 d . . . . .
H12 H 0.9657 0.9934 0.5177 0.043 Uiso 0.5 1 calc GR . . . .
C12 C 0.8498(4) 0.9207(2) 0.5475(3) 0.0198(7) Uani 1 1 d . . . . .
C13 C 0.7407(4) 0.8983(2) 0.6116(3) 0.0214(8) Uani 1 1 d . . . . .
H13 H 0.7288 0.9238 0.6717 0.026 Uiso 1 1 calc R . . . .
C14 C 0.6508(4) 0.8397(2) 0.5882(3) 0.0178(7) Uani 1 1 d . . . . .
H14 H 0.5753 0.8261 0.6308 0.021 Uiso 1 1 calc R . . . .
C15 C 0.2751(4) 0.8398(2) 0.4824(3) 0.0177(7) Uani 1 1 d . . . . .
C16 C 0.2416(4) 0.7944(2) 0.3966(3) 0.0175(7) Uani 1 1 d . . . . .
C17 C 0.1402(4) 0.7395(2) 0.4256(3) 0.0154(7) Uani 1 1 d . . . . .
C18 C 0.1207(4) 0.7471(2) 0.5297(3) 0.0166(7) Uani 1 1 d . . . . .
C19 C 0.2044(4) 0.8098(2) 0.5645(3) 0.0188(7) Uani 1 1 d . . . . .
C20 C 0.2056(5) 0.8403(3) 0.6668(3) 0.0311(10) Uani 1 1 d . . . . .
H20A H 0.2001 0.8013 0.7153 0.047 Uiso 1 1 calc GR . . . .
H20B H 0.1192 0.8721 0.6712 0.047 Uiso 1 1 calc GR . . . .
H20C H 0.2984 0.8675 0.6814 0.047 Uiso 1 1 calc GR . . . .
C21 C 0.0241(5) 0.7023(3) 0.5918(3) 0.0264(9) Uani 1 1 d . . . . .
H21A H 0.0074 0.6554 0.5603 0.040 Uiso 1 1 calc GR . . . .
H21B H -0.0725 0.7262 0.5973 0.040 Uiso 1 1 calc GR . . . .
H21C H 0.0741 0.6959 0.6584 0.040 Uiso 1 1 calc GR . . . .
C22 C 0.0663(4) 0.6848(2) 0.3586(3) 0.0230(8) Uani 1 1 d . . . . .
H22A H 0.1404 0.6637 0.3170 0.034 Uiso 1 1 calc GR . . . .
H22B H -0.0137 0.7075 0.3160 0.034 Uiso 1 1 calc GR . . . .
H22C H 0.0234 0.6472 0.3987 0.034 Uiso 1 1 calc GR . . . .
C23 C 0.2904(5) 0.8081(3) 0.2936(3) 0.0280(9) Uani 1 1 d . . . . .
H23A H 0.3941 0.8254 0.2982 0.042 Uiso 1 1 calc GR . . . .
H23B H 0.2249 0.8442 0.2604 0.042 Uiso 1 1 calc GR . . . .
H23C H 0.2840 0.7635 0.2550 0.042 Uiso 1 1 calc GR . . . .
C24 C 0.3597(5) 0.9089(2) 0.4799(4) 0.0328(10) Uani 1 1 d . . . . .
H24A H 0.3917 0.9235 0.5481 0.049 Uiso 1 1 calc GR . . . .
H24B H 0.2947 0.9459 0.4484 0.049 Uiso 1 1 calc GR . . . .
H24C H 0.4480 0.9025 0.4416 0.049 Uiso 1 1 calc GR . . . .
O25 O 0.0446(5) 0.4724(2) 0.7285(3) 0.0515(10) Uani 1 1 d . . . . .
H25 H 0.0141 0.4797 0.6688 0.077 Uiso 1 1 calc GR . . . .
C26 C 0.1238(7) 0.5336(3) 0.7663(4) 0.0490(14) Uani 1 1 d . . . . .
H26A H 0.2009 0.5187 0.8176 0.074 Uiso 1 1 calc GR . . . .
H26B H 0.0538 0.5666 0.7955 0.074 Uiso 1 1 calc GR . . . .
H26C H 0.1714 0.5576 0.7121 0.074 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.0000 0.5000 0.5000 0.0411(4) Uani 1 2 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 2.3888(8) . ?
Ir1 N1 2.065(3) . ?
Ir1 N8 2.079(3) . ?
Ir1 C15 2.215(4) . ?
Ir1 C16 2.159(4) . ?
Ir1 C17 2.185(4) . ?
Ir1 C18 2.173(4) . ?
Ir1 C19 2.193(4) . ?
N1 C2 1.339(4) . ?
N1 C6 1.362(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(5) . ?
C6 N7 1.387(5) . ?
N7 N8 1.286(4) . ?
N8 C9 1.410(5) . ?
C9 C10 1.397(5) . ?
C9 C14 1.403(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.366(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.432(6) . ?
O12 H12 0.8400 . ?
O12 C12 1.303(4) . ?
C12 C13 1.412(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.446(5) . ?
C15 C19 1.426(5) . ?
C15 C24 1.497(6) . ?
C16 C17 1.441(5) . ?
C16 C23 1.504(5) . ?
C17 C18 1.430(5) . ?
C17 C22 1.485(5) . ?
C18 C19 1.451(6) . ?
C18 C21 1.499(6) . ?
C19 C20 1.489(5) . ?
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 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O25 H25 0.8400 . ?
O25 C26 1.419(7) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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 Cl1 87.54(8) . . ?
N1 Ir1 N8 74.77(12) . . ?
N1 Ir1 C15 147.73(12) . . ?
N1 Ir1 C16 110.16(13) . . ?
N1 Ir1 C17 96.48(13) . . ?
N1 Ir1 C18 116.87(14) . . ?
N1 Ir1 C19 155.66(13) . . ?
N8 Ir1 Cl1 91.50(9) . . ?
N8 Ir1 C15 101.70(13) . . ?
N8 Ir1 C16 104.22(13) . . ?
N8 Ir1 C17 137.19(13) . . ?
N8 Ir1 C18 165.85(16) . . ?
N8 Ir1 C19 129.32(14) . . ?
C15 Ir1 Cl1 124.73(10) . . ?
C16 Ir1 Cl1 158.73(10) . . ?
C16 Ir1 C15 38.59(14) . . ?
C16 Ir1 C17 38.74(14) . . ?
C16 Ir1 C18 65.07(14) . . ?
C16 Ir1 C19 64.56(14) . . ?
C17 Ir1 Cl1 130.54(10) . . ?
C17 Ir1 C15 63.86(14) . . ?
C17 Ir1 C19 64.08(14) . . ?
C18 Ir1 Cl1 96.83(10) . . ?
C18 Ir1 C15 64.16(15) . . ?
C18 Ir1 C17 38.30(14) . . ?
C18 Ir1 C19 38.80(15) . . ?
C19 Ir1 Cl1 94.42(10) . . ?
C19 Ir1 C15 37.73(14) . . ?
C2 N1 Ir1 126.7(2) . . ?
C2 N1 C6 118.8(3) . . ?
C6 N1 Ir1 114.4(2) . . ?
N1 C2 H2 119.2 . . ?
N1 C2 C3 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 122.3(3) . . ?
N1 C6 N7 117.7(3) . . ?
N7 C6 C5 120.0(3) . . ?
N8 N7 C6 112.6(3) . . ?
N7 N8 Ir1 119.8(2) . . ?
N7 N8 C9 114.5(3) . . ?
C9 N8 Ir1 125.3(2) . . ?
C10 C9 N8 121.2(3) . . ?
C10 C9 C14 120.5(3) . . ?
C14 C9 N8 118.3(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.5(3) . . ?
C12 C11 H11 119.2 . . ?
C12 O12 H12 109.5 . . ?
O12 C12 C11 122.5(4) . . ?
O12 C12 C13 119.9(4) . . ?
C13 C12 C11 117.6(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C16 C15 Ir1 68.6(2) . . ?
C16 C15 C24 124.3(4) . . ?
C19 C15 Ir1 70.3(2) . . ?
C19 C15 C16 108.1(3) . . ?
C19 C15 C24 127.4(4) . . ?
C24 C15 Ir1 130.3(3) . . ?
C15 C16 Ir1 72.8(2) . . ?
C15 C16 C23 125.3(4) . . ?
C17 C16 Ir1 71.6(2) . . ?
C17 C16 C15 107.4(3) . . ?
C17 C16 C23 126.9(4) . . ?
C23 C16 Ir1 126.3(3) . . ?
C16 C17 Ir1 69.7(2) . . ?
C16 C17 C22 125.9(3) . . ?
C18 C17 Ir1 70.4(2) . . ?
C18 C17 C16 108.5(3) . . ?
C18 C17 C22 125.6(4) . . ?
C22 C17 Ir1 126.5(3) . . ?
C17 C18 Ir1 71.3(2) . . ?
C17 C18 C19 107.5(3) . . ?
C17 C18 C21 127.3(4) . . ?
C19 C18 Ir1 71.4(2) . . ?
C19 C18 C21 125.1(4) . . ?
C21 C18 Ir1 125.8(3) . . ?
C15 C19 Ir1 72.0(2) . . ?
C15 C19 C18 108.3(3) . . ?
C15 C19 C20 126.3(4) . . ?
C18 C19 Ir1 69.8(2) . . ?
C18 C19 C20 125.3(4) . . ?
C20 C19 Ir1 127.4(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 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 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 O25 H25 109.5 . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
O12 H12 O12 0.84 1.64 2.468(6) 167.5 3_776
O25 H25 Cl2 0.84 2.30 3.114(4) 164.3 .

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 N1 C2 C3 174.3(3) . . . . ?
Ir1 N1 C6 C5 -176.2(3) . . . . ?
Ir1 N1 C6 N7 5.5(4) . . . . ?
Ir1 N8 C9 C10 -142.5(3) . . . . ?
Ir1 N8 C9 C14 38.5(5) . . . . ?
Ir1 C15 C16 C17 63.7(3) . . . . ?
Ir1 C15 C16 C23 -122.7(4) . . . . ?
Ir1 C15 C19 C18 -60.7(3) . . . . ?
Ir1 C15 C19 C20 123.6(4) . . . . ?
Ir1 C16 C17 C18 59.9(3) . . . . ?
Ir1 C16 C17 C22 -121.0(4) . . . . ?
Ir1 C17 C18 C19 62.6(3) . . . . ?
Ir1 C17 C18 C21 -121.3(4) . . . . ?
Ir1 C18 C19 C15 62.1(3) . . . . ?
Ir1 C18 C19 C20 -122.2(4) . . . . ?
N1 C2 C3 C4 1.8(6) . . . . ?
N1 C6 N7 N8 0.7(4) . . . . ?
C2 N1 C6 C5 2.0(5) . . . . ?
C2 N1 C6 N7 -176.4(3) . . . . ?
C2 C3 C4 C5 1.7(6) . . . . ?
C3 C4 C5 C6 -3.2(6) . . . . ?
C4 C5 C6 N1 1.4(5) . . . . ?
C4 C5 C6 N7 179.8(3) . . . . ?
C5 C6 N7 N8 -177.8(3) . . . . ?
C6 N1 C2 C3 -3.6(5) . . . . ?
C6 N7 N8 Ir1 -6.7(4) . . . . ?
C6 N7 N8 C9 180.0(3) . . . . ?
N7 N8 C9 C10 30.3(5) . . . . ?
N7 N8 C9 C14 -148.7(3) . . . . ?
N8 C9 C10 C11 -178.9(3) . . . . ?
N8 C9 C14 C13 177.1(3) . . . . ?
C9 C10 C11 C12 1.5(6) . . . . ?
C10 C9 C14 C13 -1.9(6) . . . . ?
C10 C11 C12 O12 180.0(4) . . . . ?
C10 C11 C12 C13 -1.1(6) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
O12 C12 C13 C14 178.1(4) . . . . ?
C12 C13 C14 C9 2.3(6) . . . . ?
C14 C9 C10 C11 0.0(6) . . . . ?
C15 C16 C17 Ir1 -64.5(2) . . . . ?
C15 C16 C17 C18 -4.6(4) . . . . ?
C15 C16 C17 C22 174.5(4) . . . . ?
C16 C15 C19 Ir1 58.3(2) . . . . ?
C16 C15 C19 C18 -2.4(4) . . . . ?
C16 C15 C19 C20 -178.1(4) . . . . ?
C16 C17 C18 Ir1 -59.4(3) . . . . ?
C16 C17 C18 C19 3.1(4) . . . . ?
C16 C17 C18 C21 179.3(4) . . . . ?
C17 C18 C19 Ir1 -62.5(3) . . . . ?
C17 C18 C19 C15 -0.5(4) . . . . ?
C17 C18 C19 C20 175.3(4) . . . . ?
C19 C15 C16 Ir1 -59.4(2) . . . . ?
C19 C15 C16 C17 4.3(4) . . . . ?
C19 C15 C16 C23 177.9(4) . . . . ?
C21 C18 C19 Ir1 121.2(4) . . . . ?
C21 C18 C19 C15 -176.7(4) . . . . ?
C21 C18 C19 C20 -1.0(6) . . . . ?
C22 C17 C18 Ir1 121.5(4) . . . . ?
C22 C17 C18 C19 -176.0(4) . . . . ?
C22 C17 C18 C21 0.2(6) . . . . ?
C23 C16 C17 Ir1 122.0(4) . . . . ?
C23 C16 C17 C18 -178.0(4) . . . . ?
C23 C16 C17 C22 1.1(6) . . . . ?
C24 C15 C16 Ir1 124.9(4) . . . . ?
C24 C15 C16 C17 -171.4(3) . . . . ?
C24 C15 C16 C23 2.2(6) . . . . ?
C24 C15 C19 Ir1 -126.2(4) . . . . ?
C24 C15 C19 C18 173.1(4) . . . . ?
C24 C15 C19 C20 -2.6(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_gh3
_database_code_depnum_ccdc_archive 'CCDC 1921725'
loop_
_audit_author_name
_audit_author_address
'Guy J. Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-06-08 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_audit_creation_date             2016-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 Cl Ir N3 O, F6 P'
_chemical_formula_sum            'C26 H26 Cl F6 Ir N3 O P'
_chemical_formula_weight         769.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 F6 P Cl Ir'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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                   8.71914(18)
_cell_length_b                   9.9018(2)
_cell_length_c                   15.7288(3)
_cell_angle_alpha                89.3248(16)
_cell_angle_beta                 78.0376(16)
_cell_angle_gamma                88.7062(17)
_cell_volume                     1328.08(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    30461
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      37.2050
_cell_measurement_theta_min      3.1190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            66113
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         37.686
_diffrn_reflns_theta_min         2.647
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  54.00   1.00   20.50    --   29.88 -38.00 120.00   98
  2  ω     32.00 117.00   1.00   20.50    --   29.88-178.00 150.00   85
  3  ω      5.00 104.00   1.00   20.50    --   29.88  38.00 -60.00   99
  4  ω     12.00 101.00   1.00   20.50    --   29.88-149.00-108.00   89
  5  ω     -3.00 106.00   1.00   20.50    --   29.88  77.00   0.00  109
  6  ω      2.00 103.00   1.00   20.50    --   29.88  57.00 -60.00  101
  7  ω   -107.00   2.00   1.00   20.50    --  -30.82 -77.00 -30.00  109
  8  ω   -120.00 -57.00   1.00   20.50    --  -30.82-178.00 -30.00   63
  9  ω      5.00 104.00   1.00   20.50    --   29.88  38.00-180.00   99
 10  ω    -44.00  54.00   1.00   20.50    --   29.88 -38.00-120.00   98
 11  ω     -3.00 106.00   1.00   20.50    --   29.88  77.00-180.00  109
 12  ω   -118.00 -53.00   1.00   20.50    --  -30.82 178.00-120.00   65
 13  ω   -118.00 -93.00   1.00   20.50    --  -30.82 178.00 150.00   25
 14  ω   -104.00  -3.00   1.00   20.50    --  -30.82 -57.00  30.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0303335000
_diffrn_orient_matrix_UB_12      -0.0672244000
_diffrn_orient_matrix_UB_13      -0.0039708000
_diffrn_orient_matrix_UB_21      -0.0213268000
_diffrn_orient_matrix_UB_22      -0.0084284000
_diffrn_orient_matrix_UB_23      0.0457467000
_diffrn_orient_matrix_UB_31      -0.0744500000
_diffrn_orient_matrix_UB_32      -0.0233271000
_diffrn_orient_matrix_UB_33      -0.0040579000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12253
_reflns_number_total             13636
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         2.627
_refine_diff_density_min         -1.153
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         13636
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²+0.7469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0618
_refine_special_details          ?
_olex2_refinement_description    
;

The OH was located in a difference map but refined with AFIX 147 constraint.

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) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C)
2.c Idealised tetrahedral OH refined as rotating group:
 O12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.34913(6) 0.44032(6) 0.61147(4) 0.02583(10) Uani 1 1 d . . . . .
Ir1 Ir 0.52670(2) 0.35583(2) 0.69586(2) 0.01537(2) Uani 1 1 d . . . . .
N1 N 0.3399(2) 0.24564(18) 0.76154(12) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.2247(3) 0.2888(3) 0.82602(15) 0.0264(4) Uani 1 1 d . . . . .
H2 H 0.2195 0.3813 0.8420 0.032 Uiso 1 1 calc R . . . .
C3 C 0.1127(3) 0.2013(3) 0.87009(17) 0.0336(5) Uani 1 1 d . . . . .
H3 H 0.0330 0.2336 0.9165 0.040 Uiso 1 1 calc R . . . .
C4 C 0.1176(3) 0.0673(3) 0.84615(19) 0.0370(6) Uani 1 1 d . . . . .
H4 H 0.0431 0.0062 0.8768 0.044 Uiso 1 1 calc R . . . .
C5 C 0.2325(3) 0.0229(3) 0.77691(19) 0.0331(5) Uani 1 1 d . . . . .
H5 H 0.2369 -0.0684 0.7584 0.040 Uiso 1 1 calc R . . . .
C6 C 0.3410(3) 0.1154(2) 0.73541(15) 0.0238(4) Uani 1 1 d . . . . .
N7 N 0.4519(2) 0.07739(19) 0.66200(13) 0.0246(3) Uani 1 1 d . . . . .
N8 N 0.5398(2) 0.17560(17) 0.63035(11) 0.0197(3) Uani 1 1 d . . . . .
C9 C 0.6522(3) 0.1452(2) 0.55339(13) 0.0211(4) Uani 1 1 d . . . . .
C10 C 0.7153(3) 0.0154(2) 0.53754(16) 0.0298(5) Uani 1 1 d . . . . .
H10 H 0.6793 -0.0567 0.5764 0.036 Uiso 1 1 calc R . . . .
C11 C 0.8315(4) -0.0072(3) 0.46427(18) 0.0350(5) Uani 1 1 d . . . . .
H11 H 0.8771 -0.0950 0.4534 0.042 Uiso 1 1 calc R . . . .
C12 C 0.8820(3) 0.0984(3) 0.40626(15) 0.0287(4) Uani 1 1 d . . . . .
O12 O 1.0014(3) 0.0698(2) 0.33797(13) 0.0394(5) Uani 1 1 d . . . . .
H12 H 1.0144 0.1360 0.3035 0.059 Uiso 1 1 calc GR . . . .
C13 C 0.8129(3) 0.2259(2) 0.41997(15) 0.0255(4) Uani 1 1 d . . . . .
H13 H 0.8434 0.2963 0.3788 0.031 Uiso 1 1 calc R . . . .
C14 C 0.6991(3) 0.2499(2) 0.49416(14) 0.0233(4) Uani 1 1 d . . . . .
H14 H 0.6530 0.3375 0.5047 0.028 Uiso 1 1 calc R . . . .
C15 C 0.7067(3) 0.2766(2) 0.93567(14) 0.0227(4) Uani 1 1 d . . . . .
H15 H 0.7159 0.3680 0.9512 0.027 Uiso 1 1 calc R . . . .
C16 C 0.7139(3) 0.1741(3) 0.99586(15) 0.0279(4) Uani 1 1 d . . . . .
H16 H 0.7275 0.1959 1.0525 0.033 Uiso 1 1 calc R . . . .
C17 C 0.7015(3) 0.0408(3) 0.97395(16) 0.0296(5) Uani 1 1 d . . . . .
H17 H 0.7056 -0.0289 1.0155 0.036 Uiso 1 1 calc R . . . .
C18 C 0.6829(3) 0.0087(2) 0.89096(17) 0.0297(5) Uani 1 1 d . . . . .
H18 H 0.6751 -0.0831 0.8756 0.036 Uiso 1 1 calc R . . . .
C19 C 0.6756(3) 0.1104(2) 0.83061(15) 0.0243(4) Uani 1 1 d . . . . .
H19 H 0.6634 0.0879 0.7739 0.029 Uiso 1 1 calc R . . . .
C20 C 0.6861(2) 0.2458(2) 0.85241(13) 0.0188(3) Uani 1 1 d . . . . .
C21 C 0.6764(2) 0.35575(19) 0.78866(12) 0.0164(3) Uani 1 1 d . . . . .
C22 C 0.7745(2) 0.3713(2) 0.70323(13) 0.0187(3) Uani 1 1 d . . . . .
C23 C 0.7256(2) 0.4917(2) 0.66415(13) 0.0195(3) Uani 1 1 d . . . . .
C24 C 0.6031(2) 0.55627(19) 0.72773(14) 0.0189(3) Uani 1 1 d . . . . .
C25 C 0.5733(2) 0.4751(2) 0.80413(13) 0.0181(3) Uani 1 1 d . . . . .
C26 C 0.4614(3) 0.5102(2) 0.88648(14) 0.0246(4) Uani 1 1 d . . . . .
H26A H 0.3691 0.5569 0.8730 0.037 Uiso 1 1 calc GR . . . .
H26B H 0.5126 0.5692 0.9212 0.037 Uiso 1 1 calc GR . . . .
H26C H 0.4291 0.4273 0.9194 0.037 Uiso 1 1 calc GR . . . .
C27 C 0.5255(3) 0.6888(2) 0.71465(18) 0.0282(4) Uani 1 1 d . . . . .
H27A H 0.5163 0.6979 0.6538 0.042 Uiso 1 1 calc GR . . . .
H27B H 0.5884 0.7624 0.7293 0.042 Uiso 1 1 calc GR . . . .
H27C H 0.4207 0.6930 0.7523 0.042 Uiso 1 1 calc GR . . . .
C28 C 0.8051(3) 0.5540(3) 0.57987(15) 0.0284(5) Uani 1 1 d . . . . .
H28A H 0.8602 0.4835 0.5413 0.043 Uiso 1 1 calc GR . . . .
H28B H 0.8805 0.6203 0.5907 0.043 Uiso 1 1 calc GR . . . .
H28C H 0.7266 0.5992 0.5523 0.043 Uiso 1 1 calc GR . . . .
C29 C 0.9107(2) 0.2822(2) 0.66400(15) 0.0254(4) Uani 1 1 d . . . . .
H29A H 0.8986 0.1928 0.6917 0.038 Uiso 1 1 calc GR . . . .
H29B H 1.0080 0.3219 0.6730 0.038 Uiso 1 1 calc GR . . . .
H29C H 0.9148 0.2733 0.6016 0.038 Uiso 1 1 calc GR . . . .
P10 P 1.03244(7) 0.34573(6) 0.14746(4) 0.02369(10) Uani 1 1 d . . . . .
F11 F 0.8685(2) 0.2959(2) 0.20280(13) 0.0518(5) Uani 1 1 d . . . . .
F12 F 1.1972(2) 0.3911(2) 0.09358(15) 0.0577(6) Uani 1 1 d . . . . .
F13 F 1.0191(3) 0.4765(2) 0.20500(16) 0.0598(6) Uani 1 1 d . . . . .
F14 F 1.0475(2) 0.21254(18) 0.09073(13) 0.0474(4) Uani 1 1 d . . . . .
F15 F 1.1203(2) 0.2688(2) 0.21609(13) 0.0503(5) Uani 1 1 d . . . . .
F16 F 0.9424(2) 0.4200(2) 0.08152(13) 0.0467(4) Uani 1 1 d . . . . .


_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 2.3719(5) . ?
Ir1 N1 2.0655(17) . ?
Ir1 N8 2.0603(17) . ?
Ir1 C21 2.1506(19) . ?
Ir1 C22 2.1968(19) . ?
Ir1 C23 2.1906(19) . ?
Ir1 C24 2.2035(19) . ?
Ir1 C25 2.1945(19) . ?
N1 C2 1.337(3) . ?
N1 C6 1.357(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 N7 1.393(3) . ?
N7 N8 1.283(3) . ?
N8 C9 1.421(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.395(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(4) . ?
C12 O12 1.359(3) . ?
C12 C13 1.386(3) . ?
O12 H12 0.8400 . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C15 C20 1.396(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(3) . ?
C20 C21 1.484(3) . ?
C21 C22 1.444(3) . ?
C21 C25 1.461(3) . ?
C22 C23 1.432(3) . ?
C22 C29 1.494(3) . ?
C23 C24 1.446(3) . ?
C23 C28 1.496(3) . ?
C24 C25 1.419(3) . ?
C24 C27 1.495(3) . ?
C25 C26 1.490(3) . ?
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 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
P10 F11 1.5969(18) . ?
P10 F12 1.5812(19) . ?
P10 F13 1.5768(18) . ?
P10 F14 1.5887(17) . ?
P10 F15 1.6214(19) . ?
P10 F16 1.5895(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 85.45(5) . . ?
N1 Ir1 C21 101.45(7) . . ?
N1 Ir1 C22 134.88(7) . . ?
N1 Ir1 C23 163.48(7) . . ?
N1 Ir1 C24 128.46(7) . . ?
N1 Ir1 C25 99.40(7) . . ?
N8 Ir1 Cl1 89.06(5) . . ?
N8 Ir1 N1 74.69(7) . . ?
N8 Ir1 C21 112.30(7) . . ?
N8 Ir1 C22 98.85(7) . . ?
N8 Ir1 C23 118.37(7) . . ?
N8 Ir1 C24 156.69(8) . . ?
N8 Ir1 C25 150.28(7) . . ?
C21 Ir1 Cl1 158.56(5) . . ?
C21 Ir1 C22 38.78(7) . . ?
C21 Ir1 C23 65.04(8) . . ?
C21 Ir1 C24 64.64(7) . . ?
C21 Ir1 C25 39.27(7) . . ?
C22 Ir1 Cl1 139.62(6) . . ?
C22 Ir1 C24 63.70(7) . . ?
C23 Ir1 Cl1 103.98(6) . . ?
C23 Ir1 C22 38.10(8) . . ?
C23 Ir1 C24 38.43(7) . . ?
C23 Ir1 C25 64.19(7) . . ?
C24 Ir1 Cl1 95.09(6) . . ?
C25 Ir1 Cl1 119.89(5) . . ?
C25 Ir1 C22 64.28(7) . . ?
C25 Ir1 C24 37.65(8) . . ?
C2 N1 Ir1 126.96(16) . . ?
C2 N1 C6 118.93(19) . . ?
C6 N1 Ir1 114.10(14) . . ?
N1 C2 H2 119.3 . . ?
N1 C2 C3 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.1(2) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 122.3(2) . . ?
N1 C6 N7 117.60(18) . . ?
C5 C6 N7 120.0(2) . . ?
N8 N7 C6 112.02(18) . . ?
N7 N8 Ir1 120.48(15) . . ?
N7 N8 C9 115.07(17) . . ?
C9 N8 Ir1 124.21(13) . . ?
C10 C9 N8 121.2(2) . . ?
C10 C9 C14 120.7(2) . . ?
C14 C9 N8 118.09(18) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
O12 C12 C11 116.9(2) . . ?
O12 C12 C13 122.7(2) . . ?
C13 C12 C11 120.4(2) . . ?
C12 O12 H12 109.5 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C20 120.3(2) . . ?
C20 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 118.8(2) . . ?
C15 C20 C21 120.12(18) . . ?
C19 C20 C21 121.10(18) . . ?
C20 C21 Ir1 124.77(13) . . ?
C22 C21 Ir1 72.34(11) . . ?
C22 C21 C20 127.02(17) . . ?
C22 C21 C25 107.08(17) . . ?
C25 C21 Ir1 71.99(11) . . ?
C25 C21 C20 125.73(17) . . ?
C21 C22 Ir1 68.88(10) . . ?
C21 C22 C29 126.0(2) . . ?
C23 C22 Ir1 70.72(11) . . ?
C23 C22 C21 108.49(17) . . ?
C23 C22 C29 125.37(19) . . ?
C29 C22 Ir1 129.11(14) . . ?
C22 C23 Ir1 71.19(11) . . ?
C22 C23 C24 107.58(17) . . ?
C22 C23 C28 126.5(2) . . ?
C24 C23 Ir1 71.27(11) . . ?
C24 C23 C28 125.0(2) . . ?
C28 C23 Ir1 131.37(15) . . ?
C23 C24 Ir1 70.30(11) . . ?
C23 C24 C27 124.8(2) . . ?
C25 C24 Ir1 70.83(11) . . ?
C25 C24 C23 108.80(17) . . ?
C25 C24 C27 126.37(19) . . ?
C27 C24 Ir1 126.18(15) . . ?
C21 C25 Ir1 68.74(10) . . ?
C21 C25 C26 126.59(19) . . ?
C24 C25 Ir1 71.52(11) . . ?
C24 C25 C21 107.89(16) . . ?
C24 C25 C26 125.47(19) . . ?
C26 C25 Ir1 127.41(14) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
F11 P10 F15 89.08(12) . . ?
F12 P10 F11 178.27(13) . . ?
F12 P10 F14 89.31(12) . . ?
F12 P10 F15 89.41(12) . . ?
F12 P10 F16 91.97(12) . . ?
F13 P10 F11 90.15(12) . . ?
F13 P10 F12 90.67(13) . . ?
F13 P10 F14 178.92(13) . . ?
F13 P10 F15 88.82(12) . . ?
F13 P10 F16 91.16(12) . . ?
F14 P10 F11 89.84(11) . . ?
F14 P10 F15 90.10(11) . . ?
F14 P10 F16 89.92(11) . . ?
F16 P10 F11 89.53(11) . . ?
F16 P10 F15 178.62(12) . . ?

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
O12 H12 F15 0.84 1.99 2.795(3) 160.3 .

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 N1 C2 C3 -174.39(18) . . . . ?
Ir1 N1 C6 C5 174.43(19) . . . . ?
Ir1 N1 C6 N7 -8.3(2) . . . . ?
Ir1 N8 C9 C10 144.46(19) . . . . ?
Ir1 N8 C9 C14 -34.9(3) . . . . ?
Ir1 C21 C22 C23 59.84(13) . . . . ?
Ir1 C21 C22 C29 -123.7(2) . . . . ?
Ir1 C21 C25 C24 -61.12(13) . . . . ?
Ir1 C21 C25 C26 121.5(2) . . . . ?
Ir1 C22 C23 C24 62.37(13) . . . . ?
Ir1 C22 C23 C28 -128.1(2) . . . . ?
Ir1 C23 C24 C25 60.64(14) . . . . ?
Ir1 C23 C24 C27 -121.0(2) . . . . ?
Ir1 C24 C25 C21 59.36(13) . . . . ?
Ir1 C24 C25 C26 -123.3(2) . . . . ?
N1 C2 C3 C4 -1.2(4) . . . . ?
N1 C6 N7 N8 0.8(3) . . . . ?
C2 N1 C6 C5 -4.2(3) . . . . ?
C2 N1 C6 N7 173.0(2) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C4 C5 C6 N1 1.5(4) . . . . ?
C4 C5 C6 N7 -175.7(2) . . . . ?
C5 C6 N7 N8 178.1(2) . . . . ?
C6 N1 C2 C3 4.1(3) . . . . ?
C6 N7 N8 Ir1 7.6(2) . . . . ?
C6 N7 N8 C9 -177.86(18) . . . . ?
N7 N8 C9 C10 -29.9(3) . . . . ?
N7 N8 C9 C14 150.7(2) . . . . ?
N8 C9 C10 C11 -176.1(2) . . . . ?
N8 C9 C14 C13 177.5(2) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C10 C9 C14 C13 -1.9(3) . . . . ?
C10 C11 C12 O12 177.1(3) . . . . ?
C10 C11 C12 C13 -2.1(4) . . . . ?
C11 C12 C13 C14 3.5(4) . . . . ?
C12 C13 C14 C9 -1.5(3) . . . . ?
O12 C12 C13 C14 -175.6(2) . . . . ?
C14 C9 C10 C11 3.3(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C15 C20 C21 Ir1 -143.26(16) . . . . ?
C15 C20 C21 C22 123.2(2) . . . . ?
C15 C20 C21 C25 -51.2(3) . . . . ?
C16 C15 C20 C19 -1.1(3) . . . . ?
C16 C15 C20 C21 179.2(2) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C15 1.1(3) . . . . ?
C18 C19 C20 C21 -179.2(2) . . . . ?
C19 C20 C21 Ir1 37.1(3) . . . . ?
C19 C20 C21 C22 -56.4(3) . . . . ?
C19 C20 C21 C25 129.1(2) . . . . ?
C20 C15 C16 C17 0.3(4) . . . . ?
C20 C21 C22 Ir1 120.6(2) . . . . ?
C20 C21 C22 C23 -179.54(18) . . . . ?
C20 C21 C22 C29 -3.1(3) . . . . ?
C20 C21 C25 Ir1 -120.31(19) . . . . ?
C20 C21 C25 C24 178.57(18) . . . . ?
C20 C21 C25 C26 1.2(3) . . . . ?
C21 C22 C23 Ir1 -58.70(13) . . . . ?
C21 C22 C23 C24 3.7(2) . . . . ?
C21 C22 C23 C28 173.24(19) . . . . ?
C22 C21 C25 Ir1 64.30(13) . . . . ?
C22 C21 C25 C24 3.2(2) . . . . ?
C22 C21 C25 C26 -174.17(19) . . . . ?
C22 C23 C24 Ir1 -62.31(13) . . . . ?
C22 C23 C24 C25 -1.7(2) . . . . ?
C22 C23 C24 C27 176.70(19) . . . . ?
C23 C24 C25 Ir1 -60.31(13) . . . . ?
C23 C24 C25 C21 -1.0(2) . . . . ?
C23 C24 C25 C26 176.43(19) . . . . ?
C25 C21 C22 Ir1 -64.07(12) . . . . ?
C25 C21 C22 C23 -4.2(2) . . . . ?
C25 C21 C22 C29 172.20(19) . . . . ?
C27 C24 C25 Ir1 121.3(2) . . . . ?
C27 C24 C25 C21 -179.29(19) . . . . ?
C27 C24 C25 C26 -1.9(3) . . . . ?
C28 C23 C24 Ir1 127.9(2) . . . . ?
C28 C23 C24 C25 -171.43(19) . . . . ?
C28 C23 C24 C27 6.9(3) . . . . ?
C29 C22 C23 Ir1 124.8(2) . . . . ?
C29 C22 C23 C24 -172.79(18) . . . . ?
C29 C22 C23 C28 -3.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.773
_oxdiff_exptl_absorpt_empirical_full_min 0.756
