# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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data_328

#=========================================================================
# Data for compound 5 (local labelling 328_a)
#========================================================================= 

# start Validation Reply Form

_vrf_PLAT342_328                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0216 Ang.      
RESPONSE: This is presumably due to the high thermal motion of the long
butyl chains of the NHCs which is enhance by the high temperature (-50C) 
at which this crystal could be measured. However, the structure solution
and refinement are unambiguous and fully consistent with the spectroscopic
characterization of the compound. The final model is of a reasonable 
quality.
;


_vrf_PLAT910_328                 
;
PROBLEM: Missing # of FCF Reflections Below Th(Min) .....   12 Why?       
RESPONSE: Theta min = 3.0. This is the reason for the missing reflections
at low angle. It is not possible to increase the distance from the
crystal to the detector in this instrument, so we could not
collect useful additional images to overcome this alert. However this 
does not present a problem since the high number of independent
reflections (5570) collected and the high data/parameter ratio (ca. 16).
;



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H40 B F4 Ir N4 O2'
_chemical_formula_weight         695.61

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'
B B 0.0013 0.0007 '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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1442(16)
_cell_length_b                   11.7709(18)
_cell_length_c                   15.044(2)
_cell_angle_alpha                109.125(8)
_cell_angle_beta                 97.344(7)
_cell_angle_gamma                109.259(8)
_cell_volume                     1545.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    16343
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    4.369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4753
_exptl_absorpt_correction_T_max  0.4753
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'


_exptl_special_details           
; 
 'Rigaku SCX Mini, Rigaku Mercury275R CCD' 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            19692
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.25
_reflns_number_total             5570
_reflns_number_gt                4175
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r12'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
'The BF4 molecule was modeled over two positions (56:44).'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0594P)²+0.6729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5570
_refine_ls_number_parameters     357
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.74495(3) 0.86391(3) 0.83860(2) 0.07111(15) Uani 1 1 d . . .
C1 C 0.8036(9) 0.7633(9) 0.7169(5) 0.073(2) Uani 1 1 d . . .
C2 C 0.9068(12) 0.7173(14) 0.5954(7) 0.107(3) Uani 1 1 d . . .
H2 H 0.9592 0.7280 0.5494 0.129 Uiso 1 1 calc R . .
C3 C 0.8442(12) 0.6075(13) 0.6057(7) 0.104(3) Uani 1 1 d . . .
H3 H 0.8436 0.5253 0.5692 0.125 Uiso 1 1 calc R . .
C4 C 0.9455(13) 0.9557(13) 0.6789(10) 0.144(4) Uani 1 1 d DU . .
H4A H 0.8851 0.9998 0.7074 0.173 Uiso 1 1 calc R . .
H4B H 0.9511 0.9642 0.6167 0.173 Uiso 1 1 calc R . .
C5 C 1.1055(16) 1.0202(16) 0.7522(13) 0.195(5) Uani 1 1 d DU . .
H5A H 1.0997 0.9944 0.8077 0.234 Uiso 1 1 calc R . .
H5B H 1.1682 0.9846 0.7181 0.234 Uiso 1 1 calc R . .
C6 C 1.172(2) 1.1630(17) 0.7889(16) 0.226(6) Uani 1 1 d DU . .
H6A H 1.1096 1.2005 0.8218 0.271 Uiso 1 1 calc R . .
H6B H 1.1852 1.1908 0.7348 0.271 Uiso 1 1 calc R . .
C7 C 1.313(2) 1.208(2) 0.8582(16) 0.268(9) Uani 1 1 d DU . .
H7A H 1.3415 1.1346 0.8494 0.402 Uiso 1 1 calc R . .
H7B H 1.3058 1.2434 0.9245 0.402 Uiso 1 1 calc R . .
H7C H 1.3857 1.2753 0.8464 0.402 Uiso 1 1 calc R . .
C8 C 0.6930(11) 0.5400(10) 0.7142(7) 0.103(3) Uani 1 1 d D . .
H8A H 0.6540 0.5823 0.7657 0.124 Uiso 1 1 calc R . .
H8B H 0.7545 0.5040 0.7414 0.124 Uiso 1 1 calc R . .
C9 C 0.5636(12) 0.4251(10) 0.6259(8) 0.110(3) Uani 1 1 d D . .
H9A H 0.5120 0.4631 0.5926 0.132 Uiso 1 1 calc R . .
H9B H 0.6036 0.3756 0.5790 0.132 Uiso 1 1 calc R . .
C10 C 0.4631(16) 0.3371(13) 0.6560(11) 0.151(5) Uani 1 1 d D . .
H10A H 0.4158 0.3847 0.6977 0.182 Uiso 1 1 calc R . .
H10B H 0.5162 0.3059 0.6950 0.182 Uiso 1 1 calc R . .
C11 C 0.3501(15) 0.2221(16) 0.5724(11) 0.168(6) Uani 1 1 d D . .
H11A H 0.3185 0.2505 0.5229 0.252 Uiso 1 1 calc R . .
H11B H 0.2682 0.1828 0.5949 0.252 Uiso 1 1 calc R . .
H11C H 0.3900 0.1582 0.5448 0.252 Uiso 1 1 calc R . .
C12 C 0.6175(9) 0.9125(9) 0.7494(6) 0.075(2) Uani 1 1 d . . .
C13 C 0.5391(14) 1.0191(14) 0.6715(8) 0.112(3) Uani 1 1 d . . .
H13 H 0.5350 1.0871 0.6530 0.134 Uiso 1 1 calc R . .
C14 C 0.4467(13) 0.8971(14) 0.6311(8) 0.113(4) Uani 1 1 d . . .
H14 H 0.3630 0.8620 0.5796 0.136 Uiso 1 1 calc R . .
C15 C 0.7640(12) 1.1540(10) 0.8137(8) 0.104(3) Uani 1 1 d . . .
H15A H 0.8210 1.1950 0.7763 0.125 Uiso 1 1 calc R . .
H15B H 0.8278 1.1357 0.8567 0.125 Uiso 1 1 calc R . .
C16 C 0.7040(14) 1.2488(11) 0.8757(9) 0.131(4) Uani 1 1 d . . .
H16A H 0.6314 1.2582 0.8323 0.157 Uiso 1 1 calc R . .
H16B H 0.6561 1.2113 0.9181 0.157 Uiso 1 1 calc R . .
C17 C 0.8166(18) 1.3765(13) 0.9350(11) 0.166(6) Uani 1 1 d . . .
H17A H 0.8673 1.4129 0.8931 0.199 Uiso 1 1 calc R . .
H17B H 0.8871 1.3679 0.9806 0.199 Uiso 1 1 calc R . .
C18 C 0.752(2) 1.4724(16) 0.9937(13) 0.223(9) Uani 1 1 d . . .
H18A H 0.6737 1.4720 0.9495 0.334 Uiso 1 1 calc R . .
H18B H 0.8275 1.5603 1.0250 0.334 Uiso 1 1 calc R . .
H18C H 0.7166 1.4443 1.0429 0.334 Uiso 1 1 calc R . .
C19 C 0.4163(9) 0.6899(10) 0.6552(7) 0.100(3) Uani 1 1 d . . .
H19A H 0.4810 0.6606 0.6873 0.120 Uiso 1 1 calc R . .
H19B H 0.3939 0.6410 0.5847 0.120 Uiso 1 1 calc R . .
C20 C 0.2748(14) 0.6550(14) 0.6867(11) 0.151(5) Uani 1 1 d . . .
H20A H 0.2065 0.6744 0.6479 0.181 Uiso 1 1 calc R . .
H20B H 0.2338 0.5602 0.6689 0.181 Uiso 1 1 calc R . .
C21 C 0.2799(15) 0.7137(15) 0.7812(11) 0.167(6) Uani 1 1 d . . .
H21A H 0.3185 0.8084 0.7986 0.201 Uiso 1 1 calc R . .
H21B H 0.3501 0.6962 0.8202 0.201 Uiso 1 1 calc R . .
C22 C 0.1437(15) 0.6774(19) 0.8121(12) 0.197(8) Uani 1 1 d . . .
H22A H 0.0754 0.7018 0.7793 0.295 Uiso 1 1 calc R . .
H22B H 0.1646 0.7232 0.8821 0.295 Uiso 1 1 calc R . .
H22C H 0.1023 0.5837 0.7949 0.295 Uiso 1 1 calc R . .
C23 C 0.8681(9) 0.8258(8) 0.9176(6) 0.080(2) Uani 1 1 d . . .
C24 C 0.6872(11) 0.9501(11) 0.9463(7) 0.098(3) Uani 1 1 d . . .
B1 B 0.1129(17) 0.7337(18) 0.3971(11) 0.106(4) Uani 1 1 d . . .
F1 F 0.140(4) 0.849(2) 0.450(2) 0.194(12) Uani 0.56(4) 1 d P A 1
F2 F -0.008(3) 0.685(3) 0.339(3) 0.243(16) Uani 0.56(4) 1 d P A 1
F3 F 0.220(5) 0.720(5) 0.356(4) 0.21(2) Uani 0.56(4) 1 d P A 1
F1B F 0.097(6) 0.654(3) 0.3037(16) 0.168(18) Uani 0.44(4) 1 d P A 2
F2B F 0.234(5) 0.853(4) 0.420(3) 0.20(2) Uani 0.44(4) 1 d P A 2
F3B F -0.003(6) 0.761(7) 0.397(4) 0.25(3) Uani 0.44(4) 1 d P A 2
F4 F 0.1234(9) 0.6740(8) 0.4586(5) 0.156(3) Uani 1 1 d . A .
N1 N 0.8827(8) 0.8149(9) 0.6633(5) 0.091(2) Uani 1 1 d . . .
N2 N 0.7790(7) 0.6364(8) 0.6813(5) 0.084(2) Uani 1 1 d . . .
N3 N 0.6447(9) 1.0309(9) 0.7465(6) 0.091(2) Uani 1 1 d . . .
N4 N 0.4937(8) 0.8295(9) 0.6773(5) 0.089(2) Uani 1 1 d . . .
O1 O 0.9439(8) 0.8030(8) 0.9654(5) 0.119(2) Uani 1 1 d . . .
O2 O 0.6519(10) 0.9985(10) 1.0099(6) 0.149(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 C23 1.874(9) . ?
Ir1 C24 1.885(10) . ?
Ir1 C12 2.084(8) . ?
Ir1 C1 2.105(8) . ?
C1 N2 1.333(10) . ?
C1 N1 1.351(11) . ?
C2 C3 1.309(14) . ?
C2 N1 1.380(13) . ?
C2 H2 0.9400 . ?
C3 N2 1.391(11) . ?
C3 H3 0.9400 . ?
C4 N1 1.489(14) . ?
C4 C5 1.614(14) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6 1.461(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.478(15) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 N2 1.456(11) . ?
C8 C9 1.588(13) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.430(15) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.490(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 N3 1.345(11) . ?
C12 N4 1.362(11) . ?
C13 C14 1.306(16) . ?
C13 N3 1.389(13) . ?
C13 H13 0.9400 . ?
C14 N4 1.367(13) . ?
C14 H14 0.9400 . ?
C15 N3 1.469(13) . ?
C15 C16 1.548(14) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 C17 1.445(16) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.567(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 N4 1.467(12) . ?
C19 C20 1.539(13) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 C21 1.347(15) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C21 C22 1.487(16) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 O1 1.141(10) . ?
C24 O2 1.111(10) . ?
B1 F2 1.23(2) . ?
B1 F1 1.24(2) . ?
B1 F3B 1.32(3) . ?
B1 F3 1.34(2) . ?
B1 F4 1.346(14) . ?
B1 F1B 1.36(3) . ?
B1 F2B 1.43(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
C23 Ir1 C24 91.5(4) . . ?
C23 Ir1 C12 177.0(4) . . ?
C24 Ir1 C12 89.8(4) . . ?
C23 Ir1 C1 89.0(3) . . ?
C24 Ir1 C1 178.4(4) . . ?
C12 Ir1 C1 89.8(3) . . ?
N2 C1 N1 105.7(7) . . ?
N2 C1 Ir1 126.7(7) . . ?
N1 C1 Ir1 127.4(7) . . ?
C3 C2 N1 108.5(9) . . ?
C3 C2 H2 125.7 . . ?
N1 C2 H2 125.7 . . ?
C2 C3 N2 106.4(9) . . ?
C2 C3 H3 126.8 . . ?
N2 C3 H3 126.8 . . ?
N1 C4 C5 107.1(10) . . ?
N1 C4 H4A 110.3 . . ?
C5 C4 H4A 110.3 . . ?
N1 C4 H4B 110.3 . . ?
C5 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
C6 C5 C4 113.9(15) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C7 107.7(17) . . ?
C5 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
C5 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 110.3(8) . . ?
N2 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N2 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 113.0(10) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 112.9(13) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 N4 105.2(7) . . ?
N3 C12 Ir1 127.4(6) . . ?
N4 C12 Ir1 127.3(7) . . ?
C14 C13 N3 108.0(10) . . ?
C14 C13 H13 126.0 . . ?
N3 C13 H13 126.0 . . ?
C13 C14 N4 107.6(10) . . ?
C13 C14 H14 126.2 . . ?
N4 C14 H14 126.2 . . ?
N3 C15 C16 110.4(9) . . ?
N3 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
N3 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 112.2(12) . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 111.2(14) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 C20 115.1(9) . . ?
N4 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
N4 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C19 118.6(12) . . ?
C21 C20 H20A 107.7 . . ?
C19 C20 H20A 107.7 . . ?
C21 C20 H20B 107.7 . . ?
C19 C20 H20B 107.7 . . ?
H20A C20 H20B 107.1 . . ?
C20 C21 C22 118.5(13) . . ?
C20 C21 H21A 107.7 . . ?
C22 C21 H21A 107.7 . . ?
C20 C21 H21B 107.7 . . ?
C22 C21 H21B 107.7 . . ?
H21A C21 H21B 107.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C23 Ir1 179.5(9) . . ?
O2 C24 Ir1 178.5(11) . . ?
F2 B1 F1 110(2) . . ?
F2 B1 F3B 47(2) . . ?
F1 B1 F3B 67(3) . . ?
F2 B1 F3 115(3) . . ?
F1 B1 F3 113(2) . . ?
F3B B1 F3 150(2) . . ?
F2 B1 F4 114(2) . . ?
F1 B1 F4 105.2(18) . . ?
F3B B1 F4 109.5(17) . . ?
F3 B1 F4 99.3(15) . . ?
F2 B1 F1B 62(2) . . ?
F1 B1 F1B 143(2) . . ?
F3B B1 F1B 107(3) . . ?
F3 B1 F1B 53.8(16) . . ?
F4 B1 F1B 111.4(17) . . ?
F2 B1 F2B 131(3) . . ?
F1 B1 F2B 48.3(19) . . ?
F3B B1 F2B 107(3) . . ?
F3 B1 F2B 65(2) . . ?
F4 B1 F2B 114.5(16) . . ?
F1B B1 F2B 107(2) . . ?
C1 N1 C2 109.0(9) . . ?
C1 N1 C4 126.4(8) . . ?
C2 N1 C4 124.4(10) . . ?
C1 N2 C3 110.3(9) . . ?
C1 N2 C8 125.3(8) . . ?
C3 N2 C8 124.3(9) . . ?
C12 N3 C13 109.1(9) . . ?
C12 N3 C15 125.7(8) . . ?
C13 N3 C15 125.2(10) . . ?
C12 N4 C14 109.9(9) . . ?
C12 N4 C19 125.7(8) . . ?
C14 N4 C19 124.3(9) . . ?

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
C23 Ir1 C1 N2 63.3(7) . . . . ?
C24 Ir1 C1 N2 -46(14) . . . . ?
C12 Ir1 C1 N2 -119.5(7) . . . . ?
C23 Ir1 C1 N1 -111.4(7) . . . . ?
C24 Ir1 C1 N1 140(13) . . . . ?
C12 Ir1 C1 N1 65.9(7) . . . . ?
N1 C2 C3 N2 0.3(11) . . . . ?
N1 C4 C5 C6 -169.5(15) . . . . ?
C4 C5 C6 C7 177.2(15) . . . . ?
N2 C8 C9 C10 -171.6(10) . . . . ?
C8 C9 C10 C11 -174.3(11) . . . . ?
C23 Ir1 C12 N3 -42(7) . . . . ?
C24 Ir1 C12 N3 73.6(8) . . . . ?
C1 Ir1 C12 N3 -107.9(7) . . . . ?
C23 Ir1 C12 N4 134(6) . . . . ?
C24 Ir1 C12 N4 -111.0(7) . . . . ?
C1 Ir1 C12 N4 67.5(7) . . . . ?
N3 C13 C14 N4 -1.7(13) . . . . ?
N3 C15 C16 C17 -173.5(10) . . . . ?
C15 C16 C17 C18 177.6(12) . . . . ?
N4 C19 C20 C21 -57.0(17) . . . . ?
C19 C20 C21 C22 -178.5(14) . . . . ?
C24 Ir1 C23 O1 -127(100) . . . . ?
C12 Ir1 C23 O1 -12(100) . . . . ?
C1 Ir1 C23 O1 55(100) . . . . ?
C23 Ir1 C24 O2 -65(37) . . . . ?
C12 Ir1 C24 O2 118(37) . . . . ?
C1 Ir1 C24 O2 44(45) . . . . ?
N2 C1 N1 C2 -0.6(9) . . . . ?
Ir1 C1 N1 C2 175.0(6) . . . . ?
N2 C1 N1 C4 -175.9(9) . . . . ?
Ir1 C1 N1 C4 -0.3(13) . . . . ?
C3 C2 N1 C1 0.2(11) . . . . ?
C3 C2 N1 C4 175.6(10) . . . . ?
C5 C4 N1 C1 90.1(12) . . . . ?
C5 C4 N1 C2 -84.5(13) . . . . ?
N1 C1 N2 C3 0.8(9) . . . . ?
Ir1 C1 N2 C3 -174.8(6) . . . . ?
N1 C1 N2 C8 -177.6(8) . . . . ?
Ir1 C1 N2 C8 6.8(11) . . . . ?
C2 C3 N2 C1 -0.7(11) . . . . ?
C2 C3 N2 C8 177.7(9) . . . . ?
C9 C8 N2 C1 122.0(9) . . . . ?
C9 C8 N2 C3 -56.2(12) . . . . ?
N4 C12 N3 C13 -1.2(10) . . . . ?
Ir1 C12 N3 C13 175.0(6) . . . . ?
N4 C12 N3 C15 177.1(8) . . . . ?
Ir1 C12 N3 C15 -6.7(13) . . . . ?
C14 C13 N3 C12 1.9(12) . . . . ?
C14 C13 N3 C15 -176.4(10) . . . . ?
C16 C15 N3 C12 -114.4(10) . . . . ?
C16 C15 N3 C13 63.5(13) . . . . ?
N3 C12 N4 C14 0.1(10) . . . . ?
Ir1 C12 N4 C14 -176.1(6) . . . . ?
N3 C12 N4 C19 -176.5(8) . . . . ?
Ir1 C12 N4 C19 7.3(12) . . . . ?
C13 C14 N4 C12 1.0(12) . . . . ?
C13 C14 N4 C19 177.7(9) . . . . ?
C20 C19 N4 C12 105.8(11) . . . . ?
C20 C19 N4 C14 -70.4(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.087
_exptl_crystal_recrystallization_method 'Dichloromethane/pentane slow diffusion'
_database_code_depnum_ccdc_archive 'CCDC 1021458'
