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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1869253'
_audit_update_record             
;
2018-09-23 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_audit_creation_date             2018-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
loop_
_audit_author_email
p.barnard@latrobe.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H21 F4 Ir N4, C2 H3 N'
_chemical_formula_sum            'C34 H24 F4 Ir N5'
_chemical_formula_weight         770.78
_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 0.0181 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'
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      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                   9.8986(3)
_cell_length_b                   11.6908(4)
_cell_length_c                   13.1739(4)
_cell_angle_alpha                71.971(3)
_cell_angle_beta                 89.258(2)
_cell_angle_gamma                88.706(3)
_cell_volume                     1449.28(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6114
_cell_measurement_temperature    173
_cell_measurement_theta_max      73.5704
_cell_measurement_theta_min      3.5254
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.429
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9129
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.732
_diffrn_reflns_theta_min         3.528
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5543
_reflns_number_total             5672
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         3.287
_refine_diff_density_min         -2.188
_refine_diff_density_rms         0.176
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0822P)²+6.4801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1279
_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:
 C21(H21), C15(H15), C13(H13), C20(H20), C18(H18), C5(H5), C32(H32), C3(H3),
 C2(H2), C26(H26), C8(H8), C9(H9), C19(H19), C30(H30), C29(H29), C24(H24),
 C4(H4), C31(H31)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C34(H34A,H34B,H34C)
;
_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 0.25076(2) 0.18190(2) 0.73085(2) 0.03097(11) Uani 1 1 d . . . . .
N4 N 0.3312(5) 0.2605(4) 0.5823(4) 0.0345(11) Uani 1 1 d . . . . .
C16 C 0.1532(6) 0.3339(5) 0.7395(5) 0.0295(11) Uani 1 1 d . . . . .
N3 N 0.1840(5) 0.1231(5) 0.8851(4) 0.0332(10) Uani 1 1 d . . . . .
F1 F -0.0421(5) 0.4096(4) 0.9502(4) 0.0566(11) Uani 1 1 d . . . . .
F2 F 0.0515(6) 0.6443(4) 0.6004(4) 0.0638(12) Uani 1 1 d . . . . .
C7 C 0.3135(7) 0.0136(6) 0.7260(5) 0.0373(14) Uani 1 1 d . . . . .
F3 F 0.7200(4) 0.3974(4) 0.6149(4) 0.0613(12) Uani 1 1 d . . . . .
C11 C 0.0927(6) 0.3213(6) 0.8402(5) 0.0329(12) Uani 1 1 d . . . . .
C6 C 0.0749(7) 0.1145(7) 0.6767(5) 0.0401(14) Uani 1 1 d . . . . .
C27 C 0.4283(6) 0.2428(6) 0.7695(6) 0.0384(14) Uani 1 1 d . . . . .
N1 N 0.2185(6) -0.0509(5) 0.6926(4) 0.0416(12) Uani 1 1 d . . . . .
C28 C 0.4563(7) 0.3101(5) 0.5765(6) 0.0391(14) Uani 1 1 d . . . . .
C17 C 0.1157(6) 0.2063(6) 0.9222(5) 0.0342(12) Uani 1 1 d . . . . .
F4 F 0.6429(5) 0.2725(5) 0.9838(5) 0.0688(13) Uani 1 1 d . . . . .
C1 C 0.0893(7) 0.0023(6) 0.6650(5) 0.0397(14) Uani 1 1 d . . . . .
C21 C 0.2094(7) 0.0140(6) 0.9531(5) 0.0400(14) Uani 1 1 d . . . . .
H21 H 0.2541 -0.0436 0.9263 0.048 Uiso 1 1 calc R . . . .
C15 C 0.1365(7) 0.4443(6) 0.6582(6) 0.0402(14) Uani 1 1 d . . . . .
H15 H 0.1744 0.4550 0.5893 0.048 Uiso 1 1 calc R . . . .
C13 C 0.0036(7) 0.5284(6) 0.7759(7) 0.0463(16) Uani 1 1 d . . . . .
H13 H -0.0464 0.5936 0.7875 0.056 Uiso 1 1 calc R . . . .
C22 C 0.5126(6) 0.3008(6) 0.6809(6) 0.0401(14) Uani 1 1 d . . . . .
N2 N 0.4214(6) -0.0611(6) 0.7515(5) 0.0480(14) Uani 1 1 d . . . . .
C14 C 0.0646(7) 0.5370(6) 0.6792(6) 0.0441(15) Uani 1 1 d . . . . .
C20 C 0.1749(7) -0.0208(7) 1.0601(6) 0.0446(15) Uani 1 1 d . . . . .
H20 H 0.1954 -0.0997 1.1056 0.054 Uiso 1 1 calc R . . . .
C18 C 0.0775(7) 0.1765(7) 1.0292(6) 0.0445(15) Uani 1 1 d . . . . .
H18 H 0.0295 0.2337 1.0545 0.053 Uiso 1 1 calc R . . . .
C23 C 0.6367(7) 0.3440(6) 0.6994(7) 0.0474(17) Uani 1 1 d . . . . .
C5 C -0.0540(7) 0.1724(6) 0.6489(5) 0.0396(13) Uani 1 1 d . . . . .
H5 H -0.0687 0.2514 0.6530 0.047 Uiso 1 1 calc R . . . .
C32 C 0.2674(7) 0.2663(6) 0.4908(5) 0.0423(14) Uani 1 1 d . . . . .
H32 H 0.1806 0.2320 0.4952 0.051 Uiso 1 1 calc R . . . .
C3 C -0.1384(8) -0.0032(8) 0.6085(6) 0.0509(17) Uani 1 1 d . . . . .
H3 H -0.2096 -0.0437 0.5871 0.061 Uiso 1 1 calc R . . . .
C2 C -0.0150(8) -0.0568(7) 0.6326(6) 0.0479(16) Uani 1 1 d . . . . .
H2 H 0.0008 -0.1353 0.6275 0.057 Uiso 1 1 calc R . . . .
C12 C 0.0196(7) 0.4200(6) 0.8544(6) 0.0414(14) Uani 1 1 d . . . . .
C26 C 0.4759(8) 0.2359(7) 0.8734(6) 0.0452(15) Uani 1 1 d . . . . .
H26 H 0.4228 0.1992 0.9351 0.054 Uiso 1 1 calc R . . . .
C8 C 0.2713(9) -0.1635(7) 0.6962(7) 0.058(2) Uani 1 1 d . . . . .
H8 H 0.2274 -0.2235 0.6746 0.069 Uiso 1 1 calc R . . . .
C9 C 0.3938(9) -0.1706(7) 0.7354(8) 0.058(2) Uani 1 1 d . . . . .
H9 H 0.4532 -0.2386 0.7502 0.070 Uiso 1 1 calc R . . . .
C19 C 0.1091(8) 0.0637(7) 1.0988(6) 0.0466(16) Uani 1 1 d . . . . .
H19 H 0.0861 0.0442 1.1724 0.056 Uiso 1 1 calc R . . . .
C30 C 0.4499(9) 0.3690(6) 0.3847(6) 0.0517(19) Uani 1 1 d . . . . .
H30 H 0.4903 0.4061 0.3170 0.062 Uiso 1 1 calc R . . . .
C29 C 0.5170(8) 0.3639(6) 0.4760(7) 0.0481(17) Uani 1 1 d . . . . .
H29 H 0.6046 0.3966 0.4718 0.058 Uiso 1 1 calc R . . . .
C10 C 0.5440(8) -0.0348(7) 0.7991(7) 0.0529(17) Uani 1 1 d . . . . .
H10A H 0.5852 0.0373 0.7506 0.079 Uiso 1 1 calc GR . . . .
H10B H 0.6078 -0.1031 0.8117 0.079 Uiso 1 1 calc GR . . . .
H10C H 0.5217 -0.0210 0.8671 0.079 Uiso 1 1 calc GR . . . .
C24 C 0.6826(7) 0.3369(7) 0.7994(8) 0.0542(19) Uani 1 1 d . . . . .
H24 H 0.7675 0.3678 0.8098 0.065 Uiso 1 1 calc R . . . .
C4 C -0.1593(8) 0.1138(7) 0.6156(6) 0.0488(16) Uani 1 1 d . . . . .
H4 H -0.2448 0.1532 0.5978 0.059 Uiso 1 1 calc R . . . .
C31 C 0.3230(9) 0.3200(7) 0.3911(6) 0.0521(18) Uani 1 1 d . . . . .
H31 H 0.2751 0.3233 0.3282 0.062 Uiso 1 1 calc R . . . .
C25 C 0.5985(8) 0.2825(7) 0.8829(7) 0.0520(18) Uani 1 1 d . . . . .
C33 C -0.3219(9) 0.5705(9) 0.9729(8) 0.059(2) Uani 1 1 d . . . . .
C34 C -0.3255(10) 0.4911(9) 1.0817(8) 0.066(2) Uani 1 1 d . . . . .
H34A H -0.4081 0.4439 1.0933 0.099 Uiso 1 1 calc GR . . . .
H34B H -0.3245 0.5390 1.1310 0.099 Uiso 1 1 calc GR . . . .
H34C H -0.2464 0.4367 1.0946 0.099 Uiso 1 1 calc GR . . . .
N5 N -0.3209(11) 0.6324(10) 0.8889(9) 0.087(3) 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
Ir1 N4 2.046(5) . ?
Ir1 C16 2.037(6) . ?
Ir1 N3 2.039(5) . ?
Ir1 C7 2.069(6) . ?
Ir1 C6 2.145(7) . ?
Ir1 C27 2.040(7) . ?
N4 C28 1.371(9) . ?
N4 C32 1.350(9) . ?
C16 C11 1.415(8) . ?
C16 C15 1.407(9) . ?
N3 C17 1.378(8) . ?
N3 C21 1.334(8) . ?
F1 C12 1.367(8) . ?
F2 C14 1.364(8) . ?
C7 N1 1.377(9) . ?
C7 N2 1.343(9) . ?
F3 C23 1.370(9) . ?
C11 C17 1.456(9) . ?
C11 C12 1.408(9) . ?
C6 C1 1.371(10) . ?
C6 C5 1.428(10) . ?
C27 C22 1.424(9) . ?
C27 C26 1.432(10) . ?
N1 C1 1.412(10) . ?
N1 C8 1.392(9) . ?
C28 C22 1.462(11) . ?
C28 C29 1.410(10) . ?
C17 C18 1.393(9) . ?
F4 C25 1.375(10) . ?
C1 C2 1.396(10) . ?
C21 C20 1.381(10) . ?
C15 C14 1.379(10) . ?
C13 C14 1.379(11) . ?
C13 C12 1.373(11) . ?
C22 C23 1.391(10) . ?
N2 C9 1.394(10) . ?
N2 C10 1.455(10) . ?
C20 C19 1.391(11) . ?
C18 C19 1.385(11) . ?
C23 C24 1.377(13) . ?
C5 C4 1.407(10) . ?
C32 C31 1.382(10) . ?
C3 C2 1.357(12) . ?
C3 C4 1.410(11) . ?
C26 C25 1.364(11) . ?
C8 C9 1.314(13) . ?
C30 C29 1.366(13) . ?
C30 C31 1.383(13) . ?
C24 C25 1.369(13) . ?
C33 C34 1.448(14) . ?
C33 N5 1.119(14) . ?

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
N4 Ir1 C7 90.7(2) . . ?
N4 Ir1 C6 95.9(2) . . ?
C16 Ir1 N4 95.0(2) . . ?
C16 Ir1 N3 80.2(2) . . ?
C16 Ir1 C7 169.1(2) . . ?
C16 Ir1 C6 93.5(3) . . ?
C16 Ir1 C27 90.2(2) . . ?
N3 Ir1 N4 171.6(2) . . ?
N3 Ir1 C7 95.1(2) . . ?
N3 Ir1 C6 91.4(2) . . ?
N3 Ir1 C27 93.8(2) . . ?
C7 Ir1 C6 76.6(3) . . ?
C27 Ir1 N4 79.2(3) . . ?
C27 Ir1 C7 100.0(3) . . ?
C27 Ir1 C6 174.1(2) . . ?
C28 N4 Ir1 117.6(5) . . ?
C32 N4 Ir1 123.5(5) . . ?
C32 N4 C28 118.9(6) . . ?
C11 C16 Ir1 113.6(4) . . ?
C15 C16 Ir1 128.0(5) . . ?
C15 C16 C11 118.3(5) . . ?
C17 N3 Ir1 116.5(4) . . ?
C21 N3 Ir1 124.8(4) . . ?
C21 N3 C17 118.5(5) . . ?
N1 C7 Ir1 115.8(5) . . ?
N2 C7 Ir1 139.6(6) . . ?
N2 C7 N1 104.5(6) . . ?
C16 C11 C17 116.1(5) . . ?
C12 C11 C16 118.5(6) . . ?
C12 C11 C17 125.4(6) . . ?
C1 C6 Ir1 115.7(5) . . ?
C1 C6 C5 115.9(6) . . ?
C5 C6 Ir1 128.4(5) . . ?
C22 C27 Ir1 114.9(5) . . ?
C22 C27 C26 117.2(7) . . ?
C26 C27 Ir1 127.9(5) . . ?
C7 N1 C1 118.0(5) . . ?
C7 N1 C8 110.3(6) . . ?
C8 N1 C1 131.6(6) . . ?
N4 C28 C22 113.4(6) . . ?
N4 C28 C29 119.8(7) . . ?
C29 C28 C22 126.8(7) . . ?
N3 C17 C11 113.3(5) . . ?
N3 C17 C18 120.0(6) . . ?
C18 C17 C11 126.7(6) . . ?
C6 C1 N1 113.8(6) . . ?
C6 C1 C2 123.7(7) . . ?
C2 C1 N1 122.5(6) . . ?
N3 C21 C20 124.2(6) . . ?
C14 C15 C16 119.5(6) . . ?
C12 C13 C14 116.0(6) . . ?
C27 C22 C28 114.8(6) . . ?
C23 C22 C27 119.1(7) . . ?
C23 C22 C28 126.1(7) . . ?
C7 N2 C9 110.3(7) . . ?
C7 N2 C10 124.2(6) . . ?
C9 N2 C10 125.2(7) . . ?
F2 C14 C15 118.9(7) . . ?
F2 C14 C13 117.0(6) . . ?
C13 C14 C15 124.1(7) . . ?
C21 C20 C19 117.6(7) . . ?
C19 C18 C17 120.2(6) . . ?
F3 C23 C22 119.7(7) . . ?
F3 C23 C24 116.7(7) . . ?
C24 C23 C22 123.7(7) . . ?
C4 C5 C6 120.8(6) . . ?
N4 C32 C31 122.8(7) . . ?
C2 C3 C4 118.8(7) . . ?
C3 C2 C1 120.6(7) . . ?
F1 C12 C11 119.8(6) . . ?
F1 C12 C13 116.6(6) . . ?
C13 C12 C11 123.7(6) . . ?
C25 C26 C27 119.2(7) . . ?
C9 C8 N1 106.6(7) . . ?
C8 C9 N2 108.3(7) . . ?
C18 C19 C20 119.4(6) . . ?
C29 C30 C31 119.9(7) . . ?
C30 C29 C28 120.1(7) . . ?
C25 C24 C23 115.9(7) . . ?
C5 C4 C3 120.2(7) . . ?
C32 C31 C30 118.6(8) . . ?
C26 C25 F4 117.9(8) . . ?
C26 C25 C24 125.0(8) . . ?
C24 C25 F4 117.1(7) . . ?
N5 C33 C34 179.0(11) . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_date_sample_data_collection 01/07/2012
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile, ethyl acetate'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1869256'
_audit_update_record             
;
2018-09-23 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_audit_creation_date             2018-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H19 F6 Ir N4'
_chemical_formula_sum            'C32 H19 F6 Ir N4'
_chemical_formula_weight         765.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C31 H19 N5 F6 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'
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/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                   10.84307(11)
_cell_length_b                   15.66542(16)
_cell_length_c                   15.57142(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.5122(9)
_cell_angle_gamma                90
_cell_volume                     2642.44(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11033
_cell_measurement_temperature    172.97(14)
_cell_measurement_theta_max      73.6878
_cell_measurement_theta_min      2.8382
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.851
_diffrn_reflns_theta_min         4.005
_diffrn_ambient_temperature      172.97(14)
_diffrn_detector_area_resol_mean 10.3281
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0319   46.0000 -142.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega -116.00  -16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0319  -38.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega -113.00  -67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0319 -138.0000 -154.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega   13.00   70.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0319  -99.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
  5 omega   28.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0319 -138.0000   93.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   30.00   79.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  -30.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
  7 omega  128.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  125.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  8 omega   26.00   98.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  -95.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
  9 omega   96.00  122.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   81.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  -30.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega   30.00   63.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  -30.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 12 omega   53.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  -30.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega   60.00  114.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295 -125.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
 14 omega   29.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  -30.0000  -60.0000 61

#__ type_ start__ end____ width___ exp.time_
 15 omega   48.00   86.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  -95.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 16 omega   46.00  174.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295   15.0000    0.0000 128

#__ type_ start__ end____ width___ exp.time_
 17 omega  123.00  155.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295   45.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
 18 omega   96.00  122.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295 -125.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   33.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  -30.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00  130.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.5295  -77.0000  120.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0410470000
_diffrn_orient_matrix_UB_12      -0.0546224000
_diffrn_orient_matrix_UB_13      0.0759129000
_diffrn_orient_matrix_UB_21      0.0312450000
_diffrn_orient_matrix_UB_22      -0.0817481000
_diffrn_orient_matrix_UB_23      -0.0495597000
_diffrn_orient_matrix_UB_31      0.1325250000
_diffrn_orient_matrix_UB_32      0.0023402000
_diffrn_orient_matrix_UB_33      0.0398464000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5141
_reflns_number_total             5281
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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         0.740
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0205
_refine_ls_restrained_S_all      1.159
_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)+(0.0263P)²+1.8640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0509
_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:
 C9(H9), C31(H31), C15(H15), C13(H13), C18(H18), C3(H3), C26(H26), C5(H5),
 C21(H21), C30(H30), C32(H32), C24(H24), C20(H20), C8(H8), C19(H19), C29(H29)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 0.57085(2) 0.22748(2) 0.37003(2) 0.01784(5) Uani 1 1 d . . . . .
C16 C 0.5784(2) 0.22716(15) 0.23938(16) 0.0219(5) Uani 1 1 d . . . . .
F2 F 0.95954(15) 0.43170(12) 0.27816(11) 0.0373(4) Uani 1 1 d . . . . .
C7 C 0.5937(3) 0.23729(16) 0.50236(16) 0.0231(5) Uani 1 1 d . . . . .
N1 N 0.6894(2) 0.28785(14) 0.53245(14) 0.0242(4) Uani 1 1 d . . . . .
N4 N 0.44281(19) 0.32318(14) 0.36986(13) 0.0218(4) Uani 1 1 d . . . . .
F1 F 0.89464(16) 0.39808(11) 0.57249(11) 0.0367(4) Uani 1 1 d . . . . .
N3 N 0.68810(19) 0.12732(13) 0.35419(14) 0.0236(4) Uani 1 1 d . . . . .
F4 F 0.4828(2) 0.33282(15) 0.03922(12) 0.0521(5) Uani 1 1 d . . . . .
C27 C 0.4107(2) 0.15672(16) 0.36093(15) 0.0222(5) Uani 1 1 d . . . . .
C6 C 0.7257(2) 0.30677(16) 0.38385(16) 0.0212(5) Uani 1 1 d . . . . .
F5 F 0.08105(15) 0.21249(13) 0.35142(12) 0.0384(4) Uani 1 1 d . . . . .
N2 N 0.5386(2) 0.21145(15) 0.57405(15) 0.0283(5) Uani 1 1 d . . . . .
F3 F 0.7683(2) 0.11278(16) 0.08738(13) 0.0572(6) Uani 1 1 d . . . . .
C14 C 0.5419(3) 0.2781(2) 0.0949(2) 0.0363(7) Uani 1 1 d . . . . .
C22 C 0.3019(2) 0.20709(18) 0.35694(15) 0.0232(5) Uani 1 1 d . . . . .
C17 C 0.7223(2) 0.11140(17) 0.27215(18) 0.0264(5) Uani 1 1 d . . . . .
C9 C 0.5983(3) 0.2450(2) 0.64713(18) 0.0363(6) Uani 1 1 d . . . . .
H9 H 0.5767 0.2361 0.7036 0.044 Uiso 1 1 calc R . . . .
C31 C 0.3855(3) 0.47060(19) 0.3662(2) 0.0389(7) Uani 1 1 d . . . . .
H31 H 0.4087 0.5277 0.3702 0.047 Uiso 1 1 calc R . . . .
C15 C 0.5160(3) 0.28158(17) 0.18074(17) 0.0270(5) Uani 1 1 d . . . . .
H15 H 0.4575 0.3198 0.1996 0.032 Uiso 1 1 calc R . . . .
C13 C 0.6271(3) 0.2225(2) 0.0622(2) 0.0416(8) Uani 1 1 d . . . . .
H13 H 0.6442 0.2222 0.0042 0.050 Uiso 1 1 calc R . . . .
F6 F 0.27167(19) -0.05487(12) 0.35691(14) 0.0475(5) Uani 1 1 d . . . . .
C10 C 0.4317(3) 0.1557(2) 0.57531(19) 0.0368(6) Uani 1 1 d . . . . .
H10A H 0.3586 0.1876 0.5594 0.055 Uiso 1 1 calc GR . . . .
H10B H 0.4246 0.1328 0.6321 0.055 Uiso 1 1 calc GR . . . .
H10C H 0.4412 0.1098 0.5353 0.055 Uiso 1 1 calc GR . . . .
C11 C 0.6642(2) 0.16744(18) 0.20772(17) 0.0266(5) Uani 1 1 d . . . . .
C1 C 0.7632(2) 0.32653(16) 0.46996(16) 0.0225(5) Uani 1 1 d . . . . .
C18 C 0.8041(3) 0.0447(2) 0.2571(2) 0.0363(6) Uani 1 1 d . . . . .
H18 H 0.8285 0.0340 0.2016 0.044 Uiso 1 1 calc R . . . .
C12 C 0.6849(3) 0.1677(2) 0.11975(19) 0.0365(6) Uani 1 1 d . . . . .
C4 C 0.8935(2) 0.39644(17) 0.34196(18) 0.0270(5) Uani 1 1 d . . . . .
C28 C 0.3214(2) 0.29941(18) 0.35875(15) 0.0229(5) Uani 1 1 d . . . . .
C3 C 0.9297(2) 0.41633(18) 0.42583(19) 0.0293(5) Uani 1 1 d . . . . .
H3 H 0.9961 0.4523 0.4390 0.035 Uiso 1 1 calc R . . . .
C25 C 0.2817(3) 0.03185(19) 0.35602(18) 0.0334(6) Uani 1 1 d . . . . .
C26 C 0.3977(3) 0.06773(17) 0.35874(17) 0.0281(5) Uani 1 1 d . . . . .
H26 H 0.4673 0.0330 0.3591 0.034 Uiso 1 1 calc R . . . .
C23 C 0.1875(2) 0.1662(2) 0.35382(16) 0.0292(6) Uani 1 1 d . . . . .
C5 C 0.7953(2) 0.34383(16) 0.32001(16) 0.0235(5) Uani 1 1 d . . . . .
H5 H 0.7750 0.3329 0.2624 0.028 Uiso 1 1 calc R . . . .
C2 C 0.8615(2) 0.37966(17) 0.48897(17) 0.0271(5) Uani 1 1 d . . . . .
C21 C 0.7340(3) 0.07850(18) 0.4194(2) 0.0317(6) Uani 1 1 d . . . . .
H21 H 0.7107 0.0903 0.4749 0.038 Uiso 1 1 calc R . . . .
C30 C 0.2628(3) 0.4480(2) 0.3518(2) 0.0369(6) Uani 1 1 d . . . . .
H30 H 0.2026 0.4899 0.3439 0.044 Uiso 1 1 calc R . . . .
C32 C 0.4725(3) 0.40660(17) 0.37474(18) 0.0298(5) Uani 1 1 d . . . . .
H32 H 0.5550 0.4216 0.3842 0.036 Uiso 1 1 calc R . . . .
C24 C 0.1744(3) 0.0790(2) 0.35349(18) 0.0346(6) Uani 1 1 d . . . . .
H24 H 0.0971 0.0531 0.3517 0.042 Uiso 1 1 calc R . . . .
C20 C 0.8143(3) 0.0116(2) 0.4066(2) 0.0393(7) Uani 1 1 d . . . . .
H20 H 0.8445 -0.0214 0.4526 0.047 Uiso 1 1 calc R . . . .
C8 C 0.6931(3) 0.2927(2) 0.62163(17) 0.0331(6) Uani 1 1 d . . . . .
H8 H 0.7496 0.3228 0.6566 0.040 Uiso 1 1 calc R . . . .
C19 C 0.8488(3) -0.0052(2) 0.3240(2) 0.0410(7) Uani 1 1 d . . . . .
H19 H 0.9021 -0.0502 0.3136 0.049 Uiso 1 1 calc R . . . .
C29 C 0.2308(3) 0.36270(19) 0.34906(17) 0.0305(6) Uani 1 1 d . . . . .
H29 H 0.1483 0.3472 0.3407 0.037 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 C16 2.040(3) . ?
Ir1 C7 2.070(3) . ?
Ir1 N4 2.043(2) . ?
Ir1 N3 2.041(2) . ?
Ir1 C27 2.060(2) . ?
Ir1 C6 2.092(2) . ?
C16 C15 1.402(4) . ?
C16 C11 1.422(4) . ?
F2 C4 1.366(3) . ?
C7 N1 1.372(4) . ?
C7 N2 1.351(4) . ?
N1 C1 1.422(3) . ?
N1 C8 1.390(3) . ?
N4 C28 1.372(3) . ?
N4 C32 1.347(4) . ?
F1 C2 1.365(3) . ?
N3 C17 1.369(3) . ?
N3 C21 1.348(4) . ?
F4 C14 1.360(4) . ?
C27 C22 1.418(4) . ?
C27 C26 1.401(4) . ?
C6 C1 1.418(3) . ?
C6 C5 1.400(4) . ?
F5 C23 1.362(3) . ?
N2 C9 1.387(4) . ?
N2 C10 1.453(4) . ?
F3 C12 1.360(4) . ?
C14 C15 1.379(4) . ?
C14 C13 1.383(5) . ?
C22 C28 1.462(4) . ?
C22 C23 1.395(4) . ?
C17 C11 1.456(4) . ?
C17 C18 1.397(4) . ?
C9 C8 1.344(5) . ?
C31 C30 1.386(5) . ?
C31 C32 1.379(4) . ?
C13 C12 1.373(5) . ?
F6 C25 1.363(4) . ?
C11 C12 1.398(4) . ?
C1 C2 1.374(4) . ?
C18 C19 1.373(5) . ?
C4 C3 1.383(4) . ?
C4 C5 1.378(4) . ?
C28 C29 1.399(4) . ?
C3 C2 1.381(4) . ?
C25 C26 1.377(4) . ?
C25 C24 1.377(5) . ?
C23 C24 1.373(5) . ?
C21 C20 1.383(4) . ?
C30 C29 1.381(5) . ?
C20 C19 1.381(5) . ?

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
C16 Ir1 C7 169.94(10) . . ?
C16 Ir1 N4 93.30(9) . . ?
C16 Ir1 N3 79.93(10) . . ?
C16 Ir1 C27 90.05(9) . . ?
C16 Ir1 C6 92.11(10) . . ?
C7 Ir1 C6 78.06(10) . . ?
N4 Ir1 C7 89.91(9) . . ?
N4 Ir1 C27 79.86(9) . . ?
N4 Ir1 C6 96.13(9) . . ?
N3 Ir1 C7 97.44(9) . . ?
N3 Ir1 N4 172.15(8) . . ?
N3 Ir1 C27 96.07(9) . . ?
N3 Ir1 C6 88.13(9) . . ?
C27 Ir1 C7 99.91(10) . . ?
C27 Ir1 C6 175.56(9) . . ?
C15 C16 Ir1 127.5(2) . . ?
C15 C16 C11 118.6(2) . . ?
C11 C16 Ir1 113.75(19) . . ?
N1 C7 Ir1 116.01(18) . . ?
N2 C7 Ir1 139.7(2) . . ?
N2 C7 N1 104.2(2) . . ?
C7 N1 C1 116.9(2) . . ?
C7 N1 C8 111.2(2) . . ?
C8 N1 C1 131.9(2) . . ?
C28 N4 Ir1 116.69(17) . . ?
C32 N4 Ir1 123.42(18) . . ?
C32 N4 C28 119.8(2) . . ?
C17 N3 Ir1 116.66(18) . . ?
C21 N3 Ir1 123.80(19) . . ?
C21 N3 C17 119.5(2) . . ?
C22 C27 Ir1 113.62(18) . . ?
C26 C27 Ir1 128.3(2) . . ?
C26 C27 C22 118.0(2) . . ?
C1 C6 Ir1 114.98(18) . . ?
C5 C6 Ir1 128.90(18) . . ?
C5 C6 C1 116.1(2) . . ?
C7 N2 C9 110.9(3) . . ?
C7 N2 C10 125.0(2) . . ?
C9 N2 C10 124.1(2) . . ?
F4 C14 C15 118.8(3) . . ?
F4 C14 C13 117.8(3) . . ?
C15 C14 C13 123.3(3) . . ?
C27 C22 C28 115.5(2) . . ?
C23 C22 C27 118.9(3) . . ?
C23 C22 C28 125.6(2) . . ?
N3 C17 C11 114.0(2) . . ?
N3 C17 C18 119.5(3) . . ?
C18 C17 C11 126.5(3) . . ?
C8 C9 N2 107.6(3) . . ?
C32 C31 C30 118.6(3) . . ?
C14 C15 C16 119.6(3) . . ?
C12 C13 C14 116.5(3) . . ?
C16 C11 C17 115.3(2) . . ?
C12 C11 C16 118.3(3) . . ?
C12 C11 C17 126.4(3) . . ?
C6 C1 N1 114.0(2) . . ?
C2 C1 N1 124.4(2) . . ?
C2 C1 C6 121.6(2) . . ?
C19 C18 C17 120.3(3) . . ?
F3 C12 C13 116.4(3) . . ?
F3 C12 C11 120.0(3) . . ?
C13 C12 C11 123.6(3) . . ?
F2 C4 C3 117.4(2) . . ?
F2 C4 C5 119.0(2) . . ?
C5 C4 C3 123.6(3) . . ?
N4 C28 C22 114.1(2) . . ?
N4 C28 C29 119.1(3) . . ?
C29 C28 C22 126.8(2) . . ?
C2 C3 C4 116.1(2) . . ?
F6 C25 C26 118.7(3) . . ?
F6 C25 C24 117.8(3) . . ?
C26 C25 C24 123.5(3) . . ?
C25 C26 C27 119.8(3) . . ?
F5 C23 C22 120.5(3) . . ?
F5 C23 C24 116.2(3) . . ?
C24 C23 C22 123.3(3) . . ?
C4 C5 C6 120.4(2) . . ?
F1 C2 C1 120.2(3) . . ?
F1 C2 C3 117.6(2) . . ?
C1 C2 C3 122.2(2) . . ?
N3 C21 C20 122.4(3) . . ?
C29 C30 C31 119.3(3) . . ?
N4 C32 C31 122.6(3) . . ?
C23 C24 C25 116.5(3) . . ?
C19 C20 C21 118.4(3) . . ?
C9 C8 N1 106.0(3) . . ?
C18 C19 C20 119.9(3) . . ?
C30 C29 C28 120.5(3) . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_date_sample_data_collection 27/06/2013
_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_3
_database_code_depnum_ccdc_archive 'CCDC 1869254'
_audit_update_record             
;
2018-09-23 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_audit_creation_date             2018-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H25 F4 Ir N4 O2'
_chemical_formula_sum            'C34 H25 F4 Ir N4 O2'
_chemical_formula_weight         789.78
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.3830(3)
_cell_length_b                   10.6683(3)
_cell_length_c                   13.4176(4)
_cell_angle_alpha                76.274(2)
_cell_angle_beta                 82.985(2)
_cell_angle_gamma                84.990(2)
_cell_volume                     1430.37(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7657
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      30.3043
_cell_measurement_theta_min      3.1367
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11588
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.143
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5485
_reflns_number_total             5844
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         5844
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0204
_refine_ls_restrained_S_all      1.071
_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)+(0.0240P)²+1.1620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0500
_refine_ls_wR_factor_ref         0.0517
_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), C5(H5), C8(H8), C9(H9), C13(H13), C15(H15), C18(H18), C19(H19),
 C20(H20), C21(H21), C24(H24), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.0932(3) 0.2494(3) 0.9470(2) 0.0236(6) Uani 1 1 d . . . . .
C2 C 0.0506(3) 0.3004(3) 1.0318(2) 0.0273(7) Uani 1 1 d . . . . .
C3 C 0.1328(3) 0.3754(3) 1.0652(2) 0.0299(7) Uani 1 1 d . . . . .
H3 H 0.1059 0.4108 1.1236 0.036 Uiso 1 1 calc R . . . .
C4 C 0.2548(3) 0.3971(3) 1.0112(2) 0.0284(7) Uani 1 1 d . . . . .
C5 C 0.2960(3) 0.3455(3) 0.9265(2) 0.0256(7) Uani 1 1 d . . . . .
H5 H 0.3803 0.3616 0.8919 0.031 Uiso 1 1 calc R . . . .
C6 C 0.2161(3) 0.2700(3) 0.8906(2) 0.0224(6) Uani 1 1 d . . . . .
C7 C 0.0655(3) 0.1374(3) 0.8175(2) 0.0238(6) Uani 1 1 d . . . . .
C8 C -0.1023(3) 0.1187(3) 0.9441(3) 0.0319(7) Uani 1 1 d . . . . .
H8 H -0.1555 0.1287 1.0049 0.038 Uiso 1 1 calc R . . . .
C9 C -0.1264(3) 0.0497(3) 0.8776(3) 0.0327(8) Uani 1 1 d . . . . .
H9 H -0.2006 0.0014 0.8826 0.039 Uiso 1 1 calc R . . . .
C10 C -0.0164(4) 0.0030(4) 0.7124(3) 0.0378(8) Uani 1 1 d . . . . .
H10A H -0.0745 -0.0684 0.7283 0.057 Uiso 1 1 calc GR . . . .
H10B H 0.0731 -0.0301 0.6972 0.057 Uiso 1 1 calc GR . . . .
H10C H -0.0427 0.0680 0.6524 0.057 Uiso 1 1 calc GR . . . .
C11 C 0.3299(3) 0.0153(3) 0.6295(3) 0.0277(7) Uani 1 1 d . . . . .
C12 C 0.3498(4) -0.0387(3) 0.5438(3) 0.0369(8) Uani 1 1 d . . . . .
C13 C 0.3109(4) 0.0213(4) 0.4497(3) 0.0412(9) Uani 1 1 d . . . . .
H13 H 0.3252 -0.0184 0.3926 0.049 Uiso 1 1 calc R . . . .
C14 C 0.2503(4) 0.1415(4) 0.4423(3) 0.0371(8) Uani 1 1 d . . . . .
C15 C 0.2264(3) 0.2009(3) 0.5232(2) 0.0312(7) Uani 1 1 d . . . . .
H15 H 0.1838 0.2847 0.5138 0.037 Uiso 1 1 calc R . . . .
C16 C 0.2651(3) 0.1378(3) 0.6203(2) 0.0244(6) Uani 1 1 d . . . . .
C17 C 0.3705(3) -0.0441(3) 0.7322(3) 0.0284(7) Uani 1 1 d . . . . .
C18 C 0.4392(4) -0.1632(4) 0.7606(3) 0.0415(9) Uani 1 1 d . . . . .
H18 H 0.4626 -0.2147 0.7116 0.050 Uiso 1 1 calc R . . . .
C19 C 0.4731(4) -0.2064(4) 0.8603(4) 0.0499(11) Uani 1 1 d . . . . .
H19 H 0.5189 -0.2879 0.8804 0.060 Uiso 1 1 calc R . . . .
C20 C 0.4392(4) -0.1290(4) 0.9306(3) 0.0423(9) Uani 1 1 d . . . . .
H20 H 0.4619 -0.1564 0.9993 0.051 Uiso 1 1 calc R . . . .
C21 C 0.3729(3) -0.0127(3) 0.8991(3) 0.0324(8) Uani 1 1 d . . . . .
H21 H 0.3504 0.0402 0.9472 0.039 Uiso 1 1 calc R . . . .
C22 C 0.3961(3) 0.4279(3) 0.6551(2) 0.0254(7) Uani 1 1 d . . . . .
C23 C 0.5055(4) 0.4999(3) 0.6224(3) 0.0332(8) Uani 1 1 d . . . . .
C24 C 0.6290(3) 0.4490(4) 0.6315(3) 0.0385(9) Uani 1 1 d . . . . .
H24 H 0.7019 0.5002 0.6077 0.046 Uiso 1 1 calc R . . . .
C25 C 0.6433(3) 0.3194(4) 0.6769(3) 0.0371(9) Uani 1 1 d . . . . .
C26 C 0.5412(3) 0.2432(3) 0.7142(2) 0.0292(7) Uani 1 1 d . . . . .
H26 H 0.5565 0.1548 0.7470 0.035 Uiso 1 1 calc R . . . .
C27 C 0.4132(3) 0.2959(3) 0.7039(2) 0.0234(6) Uani 1 1 d . . . . .
C28 C 0.2613(3) 0.4773(3) 0.6432(2) 0.0245(6) Uani 1 1 d . . . . .
C29 C 0.2201(3) 0.6014(3) 0.5938(2) 0.0305(7) Uani 1 1 d . . . . .
H29 H 0.2821 0.6640 0.5650 0.037 Uiso 1 1 calc R . . . .
C30 C 0.0897(4) 0.6341(3) 0.5863(3) 0.0354(8) Uani 1 1 d . . . . .
H30 H 0.0612 0.7186 0.5519 0.043 Uiso 1 1 calc R . . . .
C31 C 0.0010(3) 0.5416(3) 0.6299(3) 0.0338(8) Uani 1 1 d . . . . .
H31 H -0.0896 0.5620 0.6268 0.041 Uiso 1 1 calc R . . . .
C32 C 0.0456(3) 0.4205(3) 0.6772(2) 0.0283(7) Uani 1 1 d . . . . .
H32 H -0.0159 0.3573 0.7063 0.034 Uiso 1 1 calc R . . . .
C33 C 0.3024(4) 0.5350(4) 1.1180(3) 0.0507(11) Uani 1 1 d . . . . .
H33A H 0.2214 0.5875 1.1047 0.076 Uiso 1 1 calc GR . . . .
H33B H 0.3703 0.5906 1.1234 0.076 Uiso 1 1 calc GR . . . .
H33C H 0.2884 0.4697 1.1828 0.076 Uiso 1 1 calc GR . . . .
C34 C -0.1192(4) 0.3345(4) 1.1616(3) 0.0435(9) Uani 1 1 d . . . . .
H34A H -0.1137 0.4284 1.1389 0.065 Uiso 1 1 calc GR . . . .
H34B H -0.0665 0.3011 1.2190 0.065 Uiso 1 1 calc GR . . . .
H34C H -0.2100 0.3144 1.1842 0.065 Uiso 1 1 calc GR . . . .
N1 N 0.0154(2) 0.1724(2) 0.90646(19) 0.0242(5) Uani 1 1 d . . . . .
N2 N -0.0240(2) 0.0614(3) 0.8006(2) 0.0262(6) Uani 1 1 d . . . . .
N3 N 0.3374(2) 0.0310(3) 0.8019(2) 0.0255(6) Uani 1 1 d . . . . .
N4 N 0.1727(2) 0.3864(2) 0.68460(18) 0.0216(5) Uani 1 1 d . . . . .
O1 O 0.3419(2) 0.4728(2) 1.03586(18) 0.0364(6) Uani 1 1 d . . . . .
O2 O -0.0721(2) 0.2760(3) 1.07815(18) 0.0388(6) Uani 1 1 d . . . . .
F1 F 0.4106(3) -0.1517(3) 0.5462(3) 0.0810(9) Uani 1 1 d . . . . .
F2 F 0.2121(3) 0.2070(3) 0.34811(17) 0.0570(6) Uani 1 1 d . . . . .
F3 F 0.4948(3) 0.6255(2) 0.5796(2) 0.0607(7) Uani 1 1 d . . . . .
F4 F 0.7670(2) 0.2655(3) 0.68526(18) 0.0570(7) Uani 1 1 d . . . . .
Ir2 Ir 0.24403(2) 0.20638(2) 0.75240(2) 0.02011(5) 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
C1 C2 1.383(4) . ?
C1 C6 1.409(4) . ?
C1 N1 1.436(4) . ?
C2 C3 1.398(4) . ?
C2 O2 1.365(4) . ?
C3 C4 1.390(5) . ?
C4 C5 1.383(5) . ?
C4 O1 1.381(4) . ?
C5 C6 1.403(4) . ?
C6 Ir2 2.101(3) . ?
C7 N1 1.364(4) . ?
C7 N2 1.357(4) . ?
C7 Ir2 2.068(3) . ?
C8 C9 1.341(5) . ?
C8 N1 1.383(4) . ?
C9 N2 1.381(4) . ?
C10 N2 1.454(4) . ?
C11 C12 1.391(5) . ?
C11 C16 1.402(5) . ?
C11 C17 1.470(4) . ?
C12 C13 1.364(5) . ?
C12 F1 1.306(4) . ?
C13 C14 1.366(6) . ?
C14 C15 1.370(5) . ?
C14 F2 1.377(4) . ?
C15 C16 1.405(4) . ?
C16 Ir2 2.054(3) . ?
C17 C18 1.395(5) . ?
C17 N3 1.365(4) . ?
C18 C19 1.386(6) . ?
C19 C20 1.390(6) . ?
C20 C21 1.366(5) . ?
C21 N3 1.360(4) . ?
C22 C23 1.394(4) . ?
C22 C27 1.410(4) . ?
C22 C28 1.466(4) . ?
C23 C24 1.356(5) . ?
C23 F3 1.328(4) . ?
C24 C25 1.376(6) . ?
C25 C26 1.365(5) . ?
C25 F4 1.366(4) . ?
C26 C27 1.407(4) . ?
C27 Ir2 2.035(3) . ?
C28 C29 1.388(5) . ?
C28 N4 1.368(4) . ?
C29 C30 1.378(5) . ?
C30 C31 1.385(5) . ?
C31 C32 1.366(5) . ?
C32 N4 1.347(4) . ?
C33 O1 1.418(4) . ?
C34 O2 1.424(4) . ?
N3 Ir2 2.033(3) . ?
N4 Ir2 2.037(3) . ?

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
C2 C1 C6 123.5(3) . . ?
C2 C1 N1 123.3(3) . . ?
C6 C1 N1 113.2(3) . . ?
C1 C2 C3 119.3(3) . . ?
O2 C2 C1 117.7(3) . . ?
O2 C2 C3 123.0(3) . . ?
C4 C3 C2 118.5(3) . . ?
C5 C4 C3 121.5(3) . . ?
O1 C4 C3 123.1(3) . . ?
O1 C4 C5 115.4(3) . . ?
C4 C5 C6 121.6(3) . . ?
C1 C6 Ir2 115.3(2) . . ?
C5 C6 C1 115.6(3) . . ?
C5 C6 Ir2 128.4(2) . . ?
N1 C7 Ir2 116.3(2) . . ?
N2 C7 N1 104.2(3) . . ?
N2 C7 Ir2 139.6(2) . . ?
C9 C8 N1 106.2(3) . . ?
C8 C9 N2 107.6(3) . . ?
C12 C11 C16 118.8(3) . . ?
C12 C11 C17 126.2(3) . . ?
C16 C11 C17 115.0(3) . . ?
C13 C12 C11 123.8(3) . . ?
F1 C12 C11 122.3(4) . . ?
F1 C12 C13 113.9(3) . . ?
C12 C13 C14 116.2(3) . . ?
C13 C14 C15 123.5(3) . . ?
C13 C14 F2 118.3(3) . . ?
C15 C14 F2 118.2(3) . . ?
C14 C15 C16 120.0(3) . . ?
C11 C16 C15 117.6(3) . . ?
C11 C16 Ir2 114.7(2) . . ?
C15 C16 Ir2 127.6(3) . . ?
C18 C17 C11 126.2(3) . . ?
N3 C17 C11 113.4(3) . . ?
N3 C17 C18 120.4(3) . . ?
C19 C18 C17 119.9(4) . . ?
C18 C19 C20 119.2(4) . . ?
C21 C20 C19 118.8(3) . . ?
N3 C21 C20 123.0(4) . . ?
C23 C22 C27 118.8(3) . . ?
C23 C22 C28 125.5(3) . . ?
C27 C22 C28 115.6(3) . . ?
C24 C23 C22 123.6(3) . . ?
F3 C23 C22 121.3(3) . . ?
F3 C23 C24 115.1(3) . . ?
C23 C24 C25 116.5(3) . . ?
C26 C25 C24 123.5(3) . . ?
C26 C25 F4 118.9(4) . . ?
F4 C25 C24 117.5(3) . . ?
C25 C26 C27 119.8(3) . . ?
C22 C27 Ir2 114.0(2) . . ?
C26 C27 C22 117.7(3) . . ?
C26 C27 Ir2 128.3(2) . . ?
C29 C28 C22 126.4(3) . . ?
N4 C28 C22 113.3(3) . . ?
N4 C28 C29 120.2(3) . . ?
C30 C29 C28 120.3(3) . . ?
C29 C30 C31 118.8(3) . . ?
C32 C31 C30 119.0(3) . . ?
N4 C32 C31 123.0(3) . . ?
C7 N1 C1 117.0(3) . . ?
C7 N1 C8 111.2(3) . . ?
C8 N1 C1 131.6(3) . . ?
C7 N2 C9 110.7(3) . . ?
C7 N2 C10 125.2(3) . . ?
C9 N2 C10 124.1(3) . . ?
C17 N3 Ir2 117.8(2) . . ?
C21 N3 C17 118.7(3) . . ?
C21 N3 Ir2 123.5(2) . . ?
C28 N4 Ir2 117.0(2) . . ?
C32 N4 C28 118.6(3) . . ?
C32 N4 Ir2 124.5(2) . . ?
C4 O1 C33 118.1(3) . . ?
C2 O2 C34 117.9(3) . . ?
C7 Ir2 C6 77.62(12) . . ?
C16 Ir2 C6 177.31(11) . . ?
C16 Ir2 C7 99.86(12) . . ?
C27 Ir2 C6 93.37(11) . . ?
C27 Ir2 C7 170.32(12) . . ?
C27 Ir2 C16 89.20(12) . . ?
C27 Ir2 N4 80.01(11) . . ?
N3 Ir2 C6 99.89(11) . . ?
N3 Ir2 C7 92.04(11) . . ?
N3 Ir2 C16 79.17(12) . . ?
N3 Ir2 C27 93.04(11) . . ?
N3 Ir2 N4 171.22(10) . . ?
N4 Ir2 C6 85.97(10) . . ?
N4 Ir2 C7 95.63(11) . . ?
N4 Ir2 C16 95.26(11) . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_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_6
_database_code_depnum_ccdc_archive 'CCDC 1869255'
_audit_update_record             
;
2018-09-23 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_audit_creation_date             2018-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H26 Cl F4 Ir N4, C2 H3 N'
_chemical_formula_sum            'C36 H29 Cl F4 Ir N5'
_chemical_formula_weight         835.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.0031(3)
_cell_length_b                   12.7459(4)
_cell_length_c                   15.4060(5)
_cell_angle_alpha                104.264(3)
_cell_angle_beta                 105.973(3)
_cell_angle_gamma                98.494(2)
_cell_volume                     1602.56(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9428
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.3129
_cell_measurement_theta_min      2.8793
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.307
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.885
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.3281
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6065
_reflns_number_total             6542
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.042
_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)+(0.0226P)²+0.3275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0473
_refine_ls_wR_factor_ref         0.0492
_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:
 C26(H26), C5(H5), C9(H9), C15(H15), C8(H8), C18(H18), C19(H19), C21(H21),
 C31(H31), C20(H20), C13(H13), C30(H30), C24(H24), C6(H6), C3(H3), C32(H32),
 C29(H29)
2.b Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C10(H10A,H10B,H10C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.62576(2) 0.70638(2) 0.33251(2) 0.01771(4) Uani 1 1 d . . . . .
C16 C 0.8010(3) 0.7552(2) 0.28071(19) 0.0205(6) Uani 1 1 d . . . . .
F2 F 0.9142(2) 0.75923(19) 0.07244(13) 0.0554(6) Uani 1 1 d . . . . .
F4 F 0.93314(19) 0.38733(15) 0.40059(13) 0.0343(4) Uani 1 1 d . . . . .
F3 F 0.5595(2) 0.31040(16) 0.10121(12) 0.0426(5) Uani 1 1 d . . . . .
F1 F 1.20245(19) 0.93462(17) 0.39121(13) 0.0412(5) Uani 1 1 d . . . . .
N3 N 0.8123(2) 0.77708(19) 0.45638(15) 0.0199(5) Uani 1 1 d . . . . .
C7 C 0.4531(3) 0.6764(2) 0.40047(19) 0.0213(6) Uani 1 1 d . . . . .
C27 C 0.6782(3) 0.5579(2) 0.30891(19) 0.0206(6) Uani 1 1 d . . . . .
N4 N 0.4656(3) 0.6294(2) 0.19995(16) 0.0228(5) Uani 1 1 d . . . . .
N1 N 0.3403(3) 0.5817(2) 0.38316(16) 0.0248(5) Uani 1 1 d . . . . .
C26 C 0.7922(3) 0.5225(2) 0.36966(19) 0.0230(6) Uani 1 1 d . . . . .
H26 H 0.8483 0.5687 0.4308 0.028 Uiso 1 1 calc R . . . .
N2 N 0.4250(3) 0.7508(2) 0.47128(16) 0.0232(5) Uani 1 1 d . . . . .
C25 C 0.8210(3) 0.4199(3) 0.3391(2) 0.0252(6) Uani 1 1 d . . . . .
C5 C 0.3793(5) 0.2947(3) 0.2866(3) 0.0446(9) Uani 1 1 d . . . . .
H5 H 0.4437 0.2477 0.3041 0.054 Uiso 1 1 calc R . . . .
C9 C 0.2999(3) 0.7040(3) 0.4955(2) 0.0304(7) Uani 1 1 d . . . . .
H9 H 0.2604 0.7393 0.5417 0.037 Uiso 1 1 calc R . . . .
C14 C 0.9231(4) 0.7806(3) 0.1652(2) 0.0355(8) Uani 1 1 d . . . . .
C33 C 0.0790(4) 0.5108(4) 0.2076(3) 0.0514(11) Uani 1 1 d . . . . .
H33A H -0.0052 0.5036 0.2343 0.077 Uiso 1 1 calc GR . . . .
H33B H 0.0348 0.4899 0.1399 0.077 Uiso 1 1 calc GR . . . .
H33C H 0.1389 0.5866 0.2313 0.077 Uiso 1 1 calc GR . . . .
C11 C 0.9422(3) 0.8229(2) 0.35209(19) 0.0210(6) Uani 1 1 d . . . . .
C17 C 0.9459(3) 0.8351(2) 0.44972(19) 0.0205(6) Uani 1 1 d . . . . .
C15 C 0.7953(3) 0.7348(3) 0.1867(2) 0.0292(7) Uani 1 1 d . . . . .
H15 H 0.7047 0.6899 0.1384 0.035 Uiso 1 1 calc R . . . .
C8 C 0.2464(3) 0.5988(3) 0.4403(2) 0.0314(7) Uani 1 1 d . . . . .
H8 H 0.1620 0.5469 0.4403 0.038 Uiso 1 1 calc R . . . .
C18 C 1.0717(3) 0.8969(2) 0.5320(2) 0.0259(6) Uani 1 1 d . . . . .
H18 H 1.1600 0.9406 0.5276 0.031 Uiso 1 1 calc R . . . .
C19 C 1.0651(3) 0.8930(3) 0.6193(2) 0.0283(7) Uani 1 1 d . . . . .
H19 H 1.1475 0.9351 0.6741 0.034 Uiso 1 1 calc R . . . .
C23 C 0.6353(3) 0.3825(3) 0.1901(2) 0.0282(7) Uani 1 1 d . . . . .
C21 C 0.8119(3) 0.7692(2) 0.54241(19) 0.0238(6) Uani 1 1 d . . . . .
H21 H 0.7247 0.7235 0.5461 0.029 Uiso 1 1 calc R . . . .
C31 C 0.2615(4) 0.6246(3) 0.0611(2) 0.0391(8) Uani 1 1 d . . . . .
H31 H 0.1901 0.6597 0.0299 0.047 Uiso 1 1 calc R . . . .
C22 C 0.5973(3) 0.4849(2) 0.21541(19) 0.0216(6) Uani 1 1 d . . . . .
C12 C 1.0665(3) 0.8669(3) 0.3248(2) 0.0270(6) Uani 1 1 d . . . . .
C20 C 0.9352(3) 0.8262(3) 0.6249(2) 0.0279(7) Uani 1 1 d . . . . .
H20 H 0.9307 0.8196 0.6830 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5114(4) 0.8659(2) 0.5217(2) 0.0295(7) Uani 1 1 d . . . . .
H10A H 0.5632 0.8728 0.5869 0.044 Uiso 1 1 calc GR . . . .
H10B H 0.4384 0.9137 0.5177 0.044 Uiso 1 1 calc GR . . . .
H10C H 0.5894 0.8868 0.4936 0.044 Uiso 1 1 calc GR . . . .
C13 C 1.0611(4) 0.8472(3) 0.2324(2) 0.0339(7) Uani 1 1 d . . . . .
H13 H 1.1462 0.8773 0.2160 0.041 Uiso 1 1 calc R . . . .
C30 C 0.2718(4) 0.5197(3) 0.0162(2) 0.0397(8) Uani 1 1 d . . . . .
H30 H 0.2072 0.4830 -0.0459 0.048 Uiso 1 1 calc R . . . .
C24 C 0.7466(3) 0.3468(3) 0.2495(2) 0.0302(7) Uani 1 1 d . . . . .
H24 H 0.7700 0.2779 0.2306 0.036 Uiso 1 1 calc R . . . .
C1 C 0.3141(3) 0.4723(3) 0.3177(2) 0.0270(7) Uani 1 1 d . . . . .
C6 C 0.4085(4) 0.4025(3) 0.3445(2) 0.0327(7) Uani 1 1 d . . . . .
H6 H 0.4918 0.4277 0.4015 0.039 Uiso 1 1 calc R . . . .
C3 C 0.1589(5) 0.3270(4) 0.1779(2) 0.0510(11) Uani 1 1 d . . . . .
H3 H 0.0737 0.3008 0.1217 0.061 Uiso 1 1 calc R . . . .
C28 C 0.4777(3) 0.5256(2) 0.15594(18) 0.0225(6) Uani 1 1 d . . . . .
C2 C 0.1851(4) 0.4370(3) 0.2346(2) 0.0360(8) Uani 1 1 d . . . . .
C32 C 0.3585(3) 0.6767(3) 0.1529(2) 0.0305(7) Uani 1 1 d . . . . .
H32 H 0.3500 0.7470 0.1837 0.037 Uiso 1 1 calc R . . . .
C4 C 0.2528(5) 0.2568(3) 0.2015(3) 0.0536(11) Uani 1 1 d . . . . .
C29 C 0.3780(3) 0.4697(3) 0.0634(2) 0.0312(7) Uani 1 1 d . . . . .
H29 H 0.3837 0.3981 0.0337 0.037 Uiso 1 1 calc R . . . .
C34 C 0.2222(7) 0.1389(4) 0.1367(4) 0.092(2) Uani 1 1 d . . . . .
H34A H 0.3014 0.1346 0.1059 0.138 Uiso 1 1 calc GR . . . .
H34B H 0.1189 0.1200 0.0899 0.138 Uiso 1 1 calc GR . . . .
H34C H 0.2269 0.0879 0.1735 0.138 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.56848(8) 0.89232(6) 0.33002(5) 0.02684(15) Uani 1 1 d . . . . .
C35 C 0.3133(8) 0.9956(5) 0.8898(4) 0.0859(17) Uani 1 1 d . . . . .
C36 C 0.4411(8) 1.0826(5) 0.9056(4) 0.103(2) Uani 1 1 d . . . . .
H36A H 0.4554 1.0837 0.8463 0.155 Uiso 1 1 calc GR . . . .
H36B H 0.5358 1.0719 0.9465 0.155 Uiso 1 1 calc GR . . . .
H36C H 0.4201 1.1520 0.9350 0.155 Uiso 1 1 calc GR . . . .
N5 N 0.2151(8) 0.9208(5) 0.8791(5) 0.136(2) 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
Ir1 C16 2.040(3) . ?
Ir1 N3 2.053(2) . ?
Ir1 C7 2.139(3) . ?
Ir1 C27 1.989(3) . ?
Ir1 N4 2.046(2) . ?
Ir1 Cl1 2.5059(8) . ?
C16 C11 1.417(4) . ?
C16 C15 1.391(4) . ?
F2 C14 1.365(3) . ?
F4 C25 1.371(3) . ?
F3 C23 1.367(3) . ?
F1 C12 1.361(3) . ?
N3 C17 1.360(3) . ?
N3 C21 1.354(3) . ?
C7 N1 1.375(4) . ?
C7 N2 1.366(4) . ?
C27 C26 1.396(4) . ?
C27 C22 1.426(4) . ?
N4 C28 1.365(4) . ?
N4 C32 1.350(4) . ?
N1 C8 1.381(3) . ?
N1 C1 1.447(4) . ?
C26 C25 1.365(4) . ?
N2 C9 1.380(3) . ?
N2 C10 1.459(4) . ?
C25 C24 1.376(4) . ?
C5 C6 1.383(5) . ?
C5 C4 1.397(6) . ?
C9 C8 1.332(5) . ?
C14 C15 1.372(4) . ?
C14 C13 1.372(4) . ?
C33 C2 1.486(5) . ?
C11 C17 1.464(4) . ?
C11 C12 1.391(4) . ?
C17 C18 1.401(4) . ?
C18 C19 1.375(4) . ?
C19 C20 1.377(4) . ?
C23 C22 1.387(4) . ?
C23 C24 1.372(4) . ?
C21 C20 1.381(4) . ?
C31 C30 1.375(5) . ?
C31 C32 1.375(4) . ?
C22 C28 1.458(4) . ?
C12 C13 1.369(4) . ?
C30 C29 1.369(5) . ?
C1 C6 1.378(5) . ?
C1 C2 1.391(4) . ?
C3 C2 1.404(5) . ?
C3 C4 1.365(6) . ?
C28 C29 1.397(4) . ?
C4 C34 1.522(6) . ?
C35 C36 1.396(8) . ?
C35 N5 1.145(7) . ?

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
C16 Ir1 N3 79.71(10) . . ?
C16 Ir1 C7 172.44(10) . . ?
C16 Ir1 N4 92.80(10) . . ?
C16 Ir1 Cl1 83.69(8) . . ?
N3 Ir1 C7 94.90(9) . . ?
N3 Ir1 Cl1 91.56(7) . . ?
C7 Ir1 Cl1 91.20(8) . . ?
C27 Ir1 C16 87.17(11) . . ?
C27 Ir1 N3 94.35(10) . . ?
C27 Ir1 C7 98.61(11) . . ?
C27 Ir1 N4 80.59(10) . . ?
C27 Ir1 Cl1 168.07(8) . . ?
N4 Ir1 N3 171.22(8) . . ?
N4 Ir1 C7 92.96(9) . . ?
N4 Ir1 Cl1 92.19(7) . . ?
C11 C16 Ir1 113.43(19) . . ?
C15 C16 Ir1 128.5(2) . . ?
C15 C16 C11 118.0(2) . . ?
C17 N3 Ir1 116.34(17) . . ?
C21 N3 Ir1 125.14(18) . . ?
C21 N3 C17 118.5(2) . . ?
N1 C7 Ir1 130.0(2) . . ?
N2 C7 Ir1 127.40(19) . . ?
N2 C7 N1 102.5(2) . . ?
C26 C27 Ir1 127.6(2) . . ?
C26 C27 C22 118.0(3) . . ?
C22 C27 Ir1 114.2(2) . . ?
C28 N4 Ir1 115.96(19) . . ?
C32 N4 Ir1 124.6(2) . . ?
C32 N4 C28 119.4(2) . . ?
C7 N1 C8 111.7(2) . . ?
C7 N1 C1 128.9(2) . . ?
C8 N1 C1 119.3(2) . . ?
C25 C26 C27 119.8(3) . . ?
C7 N2 C9 111.8(2) . . ?
C7 N2 C10 128.2(2) . . ?
C9 N2 C10 120.1(2) . . ?
F4 C25 C24 117.3(3) . . ?
C26 C25 F4 118.4(3) . . ?
C26 C25 C24 124.3(3) . . ?
C6 C5 C4 119.8(4) . . ?
C8 C9 N2 107.2(3) . . ?
F2 C14 C15 118.9(3) . . ?
F2 C14 C13 117.7(3) . . ?
C15 C14 C13 123.4(3) . . ?
C16 C11 C17 115.7(2) . . ?
C12 C11 C16 118.6(3) . . ?
C12 C11 C17 125.6(2) . . ?
N3 C17 C11 113.6(2) . . ?
N3 C17 C18 120.0(2) . . ?
C18 C17 C11 126.4(2) . . ?
C14 C15 C16 120.2(3) . . ?
C9 C8 N1 106.7(3) . . ?
C19 C18 C17 120.3(3) . . ?
C18 C19 C20 119.4(3) . . ?
F3 C23 C22 119.8(3) . . ?
F3 C23 C24 116.1(3) . . ?
C24 C23 C22 124.1(3) . . ?
N3 C21 C20 122.9(3) . . ?
C32 C31 C30 118.9(3) . . ?
C27 C22 C28 115.4(3) . . ?
C23 C22 C27 118.3(3) . . ?
C23 C22 C28 126.3(3) . . ?
F1 C12 C11 120.3(3) . . ?
F1 C12 C13 116.2(2) . . ?
C13 C12 C11 123.6(3) . . ?
C19 C20 C21 118.5(3) . . ?
C12 C13 C14 116.3(3) . . ?
C29 C30 C31 119.6(3) . . ?
C23 C24 C25 115.5(3) . . ?
C6 C1 N1 118.5(3) . . ?
C6 C1 C2 122.0(3) . . ?
C2 C1 N1 119.2(3) . . ?
C1 C6 C5 120.0(3) . . ?
C4 C3 C2 122.9(4) . . ?
N4 C28 C22 113.3(2) . . ?
N4 C28 C29 119.5(3) . . ?
C29 C28 C22 127.2(3) . . ?
C1 C2 C33 122.1(3) . . ?
C1 C2 C3 116.3(4) . . ?
C3 C2 C33 121.6(3) . . ?
N4 C32 C31 122.3(3) . . ?
C5 C4 C34 119.9(5) . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 C34 121.1(4) . . ?
C30 C29 C28 120.4(3) . . ?
N5 C35 C36 175.8(8) . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_exptl_crystal_mounting_method 
'Crystals were removed from the crystallisation vial and immediately coated with Paratone oil on a glass slide. Suitable single crystals were mounted in Paratone oil on a glass fibre and cooled rapidly to 173 K in a stream of cold N2 using an Oxford low temperature device. '
_olex2_submission_special_instructions 'No special instructions were received'
