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

####################################################################### 
# 
# 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. 
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data_mm009
_database_code_depnum_ccdc_archive 'CCDC 1400506'
_audit_update_record             
;
2015-05-12 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;
_audit_creation_date             2015-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H34 B Ir N6 O2'
_chemical_formula_sum            'C22 H34 B Ir N6 O2'
_chemical_formula_weight         617.56
_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'
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'
Ir Ir -1.4442 7.9887 '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                   10.6560(9)
_cell_length_b                   17.2090(16)
_cell_length_c                   14.1376(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.549(2)
_cell_angle_gamma                90
_cell_volume                     2530.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    295
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.417
_shelx_estimated_absorpt_T_min   0.076
_exptl_absorpt_coefficient_mu    5.305
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  0.359932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.1505 before and 0.0544 after correction. The Ratio of minimum to maximum transmission is 0.3599. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12453
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        23.251
_diffrn_reflns_theta_max         23.251
_diffrn_reflns_theta_min         6.816
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          295
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2532
_reflns_number_total             3526
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.119
_refine_diff_density_min         -1.659
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.064
_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)+(0.0750P)²+0.9193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C12(H12), C18(H18)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C)
;
_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 0.63147(4) 0.37896(2) 0.28368(3) 0.0445(2) Uani 1 1 d . . . . .
O1 O 0.6165(7) 0.2937(4) 0.1818(5) 0.0547(19) Uani 1 1 d . . . . .
O2 O 0.6055(7) 0.3011(4) 0.3871(5) 0.0567(19) Uani 1 1 d . . . . .
N1 N 0.3885(8) 0.4796(5) 0.2283(6) 0.048(2) Uani 1 1 d . . . . .
N2 N 0.4238(8) 0.4034(5) 0.2422(6) 0.048(2) Uani 1 1 d . . . . .
N3 N 0.5761(9) 0.5357(5) 0.3454(6) 0.053(2) Uani 1 1 d . . . . .
N4 N 0.6386(8) 0.4682(5) 0.3810(6) 0.050(2) Uani 1 1 d . . . . .
N5 N 0.5845(8) 0.5236(5) 0.1717(7) 0.053(2) Uani 1 1 d . . . . .
N6 N 0.6542(8) 0.4554(5) 0.1797(6) 0.049(2) Uani 1 1 d . . . . .
C1 C 0.2640(13) 0.4853(6) 0.2097(7) 0.055(3) Uani 1 1 d . . . . .
C2 C 0.2120(11) 0.4127(8) 0.2090(9) 0.070(4) Uani 1 1 d . . . . .
H2 H 0.1252 0.3997 0.1958 0.084 Uiso 1 1 calc R . . . .
C3 C 0.3153(12) 0.3628(7) 0.2322(8) 0.057(3) Uani 1 1 d . . . . .
C4 C 0.1898(13) 0.5610(8) 0.1872(10) 0.079(4) Uani 1 1 d . . . . .
H4A H 0.2030 0.5926 0.2446 0.119 Uiso 1 1 calc GR . . . .
H4B H 0.0998 0.5499 0.1657 0.119 Uiso 1 1 calc GR . . . .
H4C H 0.2197 0.5884 0.1372 0.119 Uiso 1 1 calc GR . . . .
C5 C 0.3129(15) 0.2758(7) 0.2414(11) 0.080(4) Uani 1 1 d . . . . .
H5A H 0.3380 0.2525 0.1866 0.121 Uiso 1 1 calc GR . . . .
H5B H 0.2275 0.2592 0.2435 0.121 Uiso 1 1 calc GR . . . .
H5C H 0.3715 0.2601 0.2998 0.121 Uiso 1 1 calc GR . . . .
C6 C 0.5898(11) 0.5880(7) 0.4208(8) 0.056(3) Uani 1 1 d . . . . .
C7 C 0.6594(12) 0.5519(7) 0.5032(9) 0.067(3) Uani 1 1 d . . . . .
H7 H 0.6812 0.5728 0.5653 0.081 Uiso 1 1 calc R . . . .
C8 C 0.6902(12) 0.4779(7) 0.4747(9) 0.062(3) Uani 1 1 d . . . . .
C9 C 0.5379(14) 0.6677(7) 0.4084(12) 0.089(5) Uani 1 1 d . . . . .
H9A H 0.6047 0.7041 0.4345 0.134 Uiso 1 1 calc GR . . . .
H9B H 0.4690 0.6728 0.4419 0.134 Uiso 1 1 calc GR . . . .
H9C H 0.5062 0.6781 0.3407 0.134 Uiso 1 1 calc GR . . . .
C10 C 0.7636(14) 0.4174(8) 0.5370(8) 0.076(4) Uani 1 1 d . . . . .
H10A H 0.7211 0.3682 0.5229 0.114 Uiso 1 1 calc GR . . . .
H10B H 0.7688 0.4304 0.6038 0.114 Uiso 1 1 calc GR . . . .
H10C H 0.8487 0.4142 0.5250 0.114 Uiso 1 1 calc GR . . . .
C11 C 0.6021(11) 0.5626(7) 0.0916(7) 0.055(3) Uani 1 1 d . . . . .
C12 C 0.6845(12) 0.5187(7) 0.0511(9) 0.061(3) Uani 1 1 d . . . . .
H12 H 0.7158 0.5318 -0.0033 0.073 Uiso 1 1 calc R . . . .
C13 C 0.7121(10) 0.4533(6) 0.1036(7) 0.050(3) Uani 1 1 d . . . . .
C14 C 0.5409(14) 0.6398(7) 0.0636(10) 0.077(4) Uani 1 1 d . . . . .
H14A H 0.4694 0.6465 0.0941 0.115 Uiso 1 1 calc GR . . . .
H14B H 0.5113 0.6420 -0.0055 0.115 Uiso 1 1 calc GR . . . .
H14C H 0.6027 0.6803 0.0844 0.115 Uiso 1 1 calc GR . . . .
C15 C 0.7998(13) 0.3877(8) 0.0890(9) 0.074(4) Uani 1 1 d . . . . .
H15A H 0.8533 0.3733 0.1502 0.111 Uiso 1 1 calc GR . . . .
H15B H 0.8529 0.4043 0.0459 0.111 Uiso 1 1 calc GR . . . .
H15C H 0.7492 0.3438 0.0614 0.111 Uiso 1 1 calc GR . . . .
C16 C 0.6140(14) 0.1701(8) 0.1138(9) 0.077(4) Uani 1 1 d . . . . .
H16A H 0.5320 0.1769 0.0704 0.116 Uiso 1 1 calc GR . . . .
H16B H 0.6243 0.1168 0.1336 0.116 Uiso 1 1 calc GR . . . .
H16C H 0.6811 0.1843 0.0814 0.116 Uiso 1 1 calc GR . . . .
C17 C 0.6215(11) 0.2215(7) 0.2024(9) 0.058(3) Uani 1 1 d . . . . .
C18 C 0.6269(11) 0.1891(6) 0.2940(10) 0.063(3) Uani 1 1 d . . . . .
H18 H 0.6393 0.1357 0.3001 0.076 Uiso 1 1 calc R . . . .
C19 C 0.6158(11) 0.2283(6) 0.3737(10) 0.060(3) Uani 1 1 d . . . . .
C20 C 0.6059(15) 0.1813(7) 0.4628(10) 0.080(4) Uani 1 1 d . . . . .
H20A H 0.6774 0.1936 0.5149 0.119 Uiso 1 1 calc GR . . . .
H20B H 0.6071 0.1269 0.4482 0.119 Uiso 1 1 calc GR . . . .
H20C H 0.5271 0.1939 0.4817 0.119 Uiso 1 1 calc GR . . . .
C21 C 0.8275(12) 0.3551(7) 0.3240(9) 0.064(3) Uani 1 1 d . . . . .
H21A H 0.8433 0.3258 0.3840 0.077 Uiso 1 1 calc R . . . .
H21B H 0.8506 0.3221 0.2748 0.077 Uiso 1 1 calc R . . . .
C22 C 0.9181(12) 0.4270(9) 0.3385(12) 0.088(4) Uani 1 1 d . . . . .
H22A H 0.9131 0.4525 0.2774 0.132 Uiso 1 1 calc GR . . . .
H22B H 1.0050 0.4105 0.3639 0.132 Uiso 1 1 calc GR . . . .
H22C H 0.8923 0.4625 0.3831 0.132 Uiso 1 1 calc GR . . . .
B1 B 0.4995(12) 0.5400(7) 0.2407(9) 0.053(3) Uani 1 1 d . . . . .
H1 H 0.4628 0.5922 0.2280 0.063 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 O1 2.038(7) . ?
Ir1 O2 2.046(7) . ?
Ir1 N2 2.203(9) . ?
Ir1 N4 2.053(8) . ?
Ir1 N6 2.026(8) . ?
Ir1 C21 2.084(12) . ?
O1 C17 1.275(13) . ?
O2 C19 1.275(12) . ?
N1 N2 1.367(12) . ?
N1 C1 1.299(13) . ?
N1 B1 1.556(15) . ?
N2 C3 1.331(15) . ?
N3 N4 1.379(12) . ?
N3 C6 1.378(13) . ?
N3 B1 1.529(15) . ?
N4 C8 1.329(14) . ?
N5 N6 1.380(12) . ?
N5 C11 1.365(13) . ?
N5 B1 1.495(15) . ?
N6 C13 1.352(12) . ?
C1 C2 1.366(17) . ?
C1 C4 1.522(15) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(17) . ?
C3 C5 1.504(16) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.385(17) . ?
C6 C9 1.476(17) . ?
C7 H7 0.9300 . ?
C7 C8 1.395(16) . ?
C8 C10 1.475(18) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.374(16) . ?
C11 C14 1.494(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.345(15) . ?
C13 C15 1.508(16) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C17 1.520(16) . ?
C17 C18 1.400(16) . ?
C18 H18 0.9300 . ?
C18 C19 1.340(16) . ?
C19 C20 1.520(17) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.555(19) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
B1 H1 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
O1 Ir1 O2 91.8(3) . . ?
O1 Ir1 N2 91.7(3) . . ?
O1 Ir1 N4 176.8(3) . . ?
O1 Ir1 C21 88.4(4) . . ?
O2 Ir1 N2 91.8(3) . . ?
O2 Ir1 N4 90.1(3) . . ?
O2 Ir1 C21 87.6(4) . . ?
N4 Ir1 N2 85.7(3) . . ?
N4 Ir1 C21 94.3(4) . . ?
N6 Ir1 O1 87.6(3) . . ?
N6 Ir1 O2 179.0(3) . . ?
N6 Ir1 N2 87.4(3) . . ?
N6 Ir1 N4 90.4(4) . . ?
N6 Ir1 C21 93.2(4) . . ?
C21 Ir1 N2 179.4(4) . . ?
C17 O1 Ir1 123.2(7) . . ?
C19 O2 Ir1 120.5(7) . . ?
N2 N1 B1 116.5(8) . . ?
C1 N1 N2 109.8(8) . . ?
C1 N1 B1 133.6(9) . . ?
N1 N2 Ir1 116.8(6) . . ?
C3 N2 Ir1 136.7(8) . . ?
C3 N2 N1 106.4(9) . . ?
N4 N3 B1 120.5(8) . . ?
C6 N3 N4 107.8(9) . . ?
C6 N3 B1 131.5(9) . . ?
N3 N4 Ir1 116.2(6) . . ?
C8 N4 Ir1 135.1(8) . . ?
C8 N4 N3 108.7(9) . . ?
N6 N5 B1 119.9(8) . . ?
C11 N5 N6 108.5(9) . . ?
C11 N5 B1 131.3(10) . . ?
N5 N6 Ir1 117.7(6) . . ?
C13 N6 Ir1 135.0(8) . . ?
C13 N6 N5 106.8(8) . . ?
N1 C1 C2 109.1(10) . . ?
N1 C1 C4 124.7(11) . . ?
C2 C1 C4 126.2(12) . . ?
C1 C2 H2 127.3 . . ?
C1 C2 C3 105.5(11) . . ?
C3 C2 H2 127.3 . . ?
N2 C3 C2 109.2(11) . . ?
N2 C3 C5 122.9(11) . . ?
C2 C3 C5 127.8(11) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 107.8(10) . . ?
N3 C6 C9 122.7(11) . . ?
C7 C6 C9 129.5(11) . . ?
C6 C7 H7 126.8 . . ?
C6 C7 C8 106.4(11) . . ?
C8 C7 H7 126.8 . . ?
N4 C8 C7 109.3(11) . . ?
N4 C8 C10 123.9(11) . . ?
C7 C8 C10 126.8(11) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 C12 106.9(10) . . ?
N5 C11 C14 121.7(11) . . ?
C12 C11 C14 131.4(11) . . ?
C11 C12 H12 125.9 . . ?
C13 C12 C11 108.2(10) . . ?
C13 C12 H12 125.9 . . ?
N6 C13 C15 122.2(10) . . ?
C12 C13 N6 109.5(10) . . ?
C12 C13 C15 128.1(11) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
O1 C17 C16 112.8(11) . . ?
O1 C17 C18 126.2(10) . . ?
C18 C17 C16 121.0(11) . . ?
C17 C18 H18 117.1 . . ?
C19 C18 C17 125.8(10) . . ?
C19 C18 H18 117.1 . . ?
O2 C19 C18 130.2(11) . . ?
O2 C19 C20 112.0(11) . . ?
C18 C19 C20 117.7(10) . . ?
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 . . ?
Ir1 C21 H21A 108.3 . . ?
Ir1 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C22 C21 Ir1 115.9(9) . . ?
C22 C21 H21A 108.3 . . ?
C22 C21 H21B 108.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 B1 H1 109.2 . . ?
N3 B1 N1 108.0(9) . . ?
N3 B1 H1 109.2 . . ?
N5 B1 N1 110.7(9) . . ?
N5 B1 N3 110.6(9) . . ?
N5 B1 H1 109.2 . . ?

_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_vero_01
_database_code_depnum_ccdc_archive 'CCDC 1400507'
_audit_update_record             
;
2015-05-12 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;
_audit_creation_date             2015-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H36 B Ir N6 O2'
_chemical_formula_sum            'C24 H36 B Ir N6 O2'
_chemical_formula_weight         643.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H30 B1 O2 Ir1 N6'
_chemical_oxdiff_usercomment     'Cristales rojos carbeno Acac'
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'
Ir Ir -1.4442 7.9887 '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                   12.9841(2)
_cell_length_b                   14.2878(2)
_cell_length_c                   14.0320(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.2716(15)
_cell_angle_gamma                90
_cell_volume                     2582.21(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    37312
_cell_measurement_temperature    294
_cell_measurement_theta_max      28.7470
_cell_measurement_theta_min      3.2450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31410
_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.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            123703
_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         3.163
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3659
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  156.0000 -175.7382 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -30.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672   19.0000 -150.0000 121

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672   57.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672   57.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
  5 omega  -17.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672   57.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00   52.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672  -99.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
  7 omega  -62.00   40.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672  -57.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
  8 omega   14.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672 -153.0000   81.0876 73

#__ type_ start__ end____ width___ exp.time_
  9 omega  -79.00  -31.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  145.0000  -22.4957 48

#__ type_ start__ end____ width___ exp.time_
 10 omega  -85.00  -36.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  153.0000  131.8626 49

#__ type_ start__ end____ width___ exp.time_
 11 omega  -84.00  -35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  152.0000 -147.9658 49

#__ type_ start__ end____ width___ exp.time_
 12 omega  -85.00  -36.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  153.0000   76.7678 49

#__ type_ start__ end____ width___ exp.time_
 13 omega  -33.00   50.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672  -92.0000  107.6209 83

#__ type_ start__ end____ width___ exp.time_
 14 omega  -20.00   56.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672 -105.0000  -23.6169 76

#__ type_ start__ end____ width___ exp.time_
 15 omega  -17.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672   57.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
 16 omega  -67.00  -19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  126.0000  162.4878 48

#__ type_ start__ end____ width___ exp.time_
 17 omega  -80.00  -32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  147.0000  101.2151 48

#__ type_ start__ end____ width___ exp.time_
 18 omega  -77.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672    0.0000 -180.0000 177

#__ type_ start__ end____ width___ exp.time_
 19 omega  -77.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672    0.0000 -120.0000 177

#__ type_ start__ end____ width___ exp.time_
 20 omega  -77.00  -43.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672    0.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
 21 omega  -77.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.3672    0.0000 -150.0000 177
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0319712000
_diffrn_orient_matrix_UB_12      0.0398745000
_diffrn_orient_matrix_UB_13      -0.0029028000
_diffrn_orient_matrix_UB_21      -0.0048663000
_diffrn_orient_matrix_UB_22      0.0110508000
_diffrn_orient_matrix_UB_23      0.0485038000
_diffrn_orient_matrix_UB_31      0.0445890000
_diffrn_orient_matrix_UB_32      -0.0274161000
_diffrn_orient_matrix_UB_33      0.0153484000
_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                4560
_reflns_number_total             5261
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         4.318
_refine_diff_density_min         -2.175
_refine_diff_density_rms         0.238
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.128
_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)+(0.0840P)²+4.3492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1295
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C12(H12)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_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 0.44810(2) 0.40329(2) 0.75797(2) 0.03278(12) Uani 1 1 d . . . . .
O1 O 0.3195(3) 0.4405(3) 0.6663(3) 0.0443(9) Uani 1 1 d . . . . .
O2 O 0.0660(5) 0.4363(6) 0.8178(6) 0.097(2) Uani 1 1 d . . . . .
N1 N 0.6067(4) 0.5614(4) 0.7861(3) 0.0379(10) Uani 1 1 d . . . . .
N2 N 0.5027(4) 0.5468(3) 0.7821(4) 0.0397(11) Uani 1 1 d . . . . .
N3 N 0.6651(4) 0.4037(3) 0.8531(4) 0.0362(11) Uani 1 1 d . . . . .
N4 N 0.5716(4) 0.3597(3) 0.8529(3) 0.0384(10) Uani 1 1 d . . . . .
N5 N 0.6524(4) 0.4351(4) 0.6763(4) 0.0398(11) Uani 1 1 d . . . . .
N6 N 0.5535(5) 0.4077(3) 0.6478(4) 0.0368(12) Uani 1 1 d . . . . .
C1 C 0.6261(5) 0.6548(4) 0.7864(4) 0.0441(14) Uani 1 1 d . . . . .
C2 C 0.5335(5) 0.7002(5) 0.7842(5) 0.0493(15) Uani 1 1 d . . . . .
H2 H 0.5230 0.7646 0.7835 0.059 Uiso 1 1 calc R . . . .
C3 C 0.4579(5) 0.6310(5) 0.7833(5) 0.0470(14) Uani 1 1 d . . . . .
C4 C 0.7314(6) 0.6937(5) 0.7859(7) 0.065(2) Uani 1 1 d . . . . .
H4A H 0.7708 0.6846 0.8479 0.098 Uiso 1 1 calc GR . . . .
H4B H 0.7267 0.7594 0.7717 0.098 Uiso 1 1 calc GR . . . .
H4C H 0.7653 0.6623 0.7380 0.098 Uiso 1 1 calc GR . . . .
C5 C 0.3435(5) 0.6435(5) 0.7780(6) 0.0566(17) Uani 1 1 d . . . . .
H5A H 0.3110 0.6250 0.7156 0.085 Uiso 1 1 calc GR . . . .
H5B H 0.3281 0.7080 0.7889 0.085 Uiso 1 1 calc GR . . . .
H5C H 0.3176 0.6055 0.8261 0.085 Uiso 1 1 calc GR . . . .
C6 C 0.7350(5) 0.3652(5) 0.9211(5) 0.0461(14) Uani 1 1 d . . . . .
C7 C 0.6854(5) 0.2959(5) 0.9647(5) 0.0514(15) Uani 1 1 d . . . . .
H7 H 0.7148 0.2574 1.0143 0.062 Uiso 1 1 calc R . . . .
C8 C 0.5843(5) 0.2935(4) 0.9218(4) 0.0452(13) Uani 1 1 d . . . . .
C9 C 0.8453(6) 0.3974(6) 0.9385(7) 0.067(2) Uani 1 1 d . . . . .
H9A H 0.8814 0.3771 0.8866 0.100 Uiso 1 1 calc GR . . . .
H9B H 0.8781 0.3713 0.9977 0.100 Uiso 1 1 calc GR . . . .
H9C H 0.8472 0.4644 0.9424 0.100 Uiso 1 1 calc GR . . . .
C10 C 0.5012(6) 0.2278(5) 0.9450(5) 0.0627(19) Uani 1 1 d . . . . .
H10A H 0.4359 0.2460 0.9101 0.094 Uiso 1 1 calc GR . . . .
H10B H 0.4966 0.2299 1.0127 0.094 Uiso 1 1 calc GR . . . .
H10C H 0.5180 0.1653 0.9271 0.094 Uiso 1 1 calc GR . . . .
C11 C 0.7088(5) 0.4319(5) 0.6025(5) 0.0502(15) Uani 1 1 d . . . . .
C12 C 0.6434(7) 0.4035(4) 0.5239(5) 0.056(2) Uani 1 1 d . . . . .
H12 H 0.6608 0.3951 0.4622 0.067 Uiso 1 1 calc R . . . .
C13 C 0.5460(6) 0.3895(4) 0.5532(5) 0.0460(15) Uani 1 1 d . . . . .
C14 C 0.8209(6) 0.4580(7) 0.6122(7) 0.077(2) Uani 1 1 d . . . . .
H14A H 0.8274 0.5249 0.6145 0.116 Uiso 1 1 calc GR . . . .
H14B H 0.8512 0.4343 0.5581 0.116 Uiso 1 1 calc GR . . . .
H14C H 0.8561 0.4315 0.6703 0.116 Uiso 1 1 calc GR . . . .
C15 C 0.4483(6) 0.3595(5) 0.4946(5) 0.0593(17) Uani 1 1 d . . . . .
H15A H 0.4472 0.2925 0.4894 0.089 Uiso 1 1 calc GR . . . .
H15B H 0.4447 0.3865 0.4316 0.089 Uiso 1 1 calc GR . . . .
H15C H 0.3900 0.3801 0.5248 0.089 Uiso 1 1 calc GR . . . .
C16 C 0.1371(6) 0.4471(7) 0.6383(6) 0.072(2) Uani 1 1 d . . . . .
H16A H 0.1089 0.5068 0.6527 0.109 Uiso 1 1 calc GR . . . .
H16B H 0.0881 0.3987 0.6477 0.109 Uiso 1 1 calc GR . . . .
H16C H 0.1510 0.4464 0.5727 0.109 Uiso 1 1 calc GR . . . .
C17 C 0.2357(5) 0.4304(5) 0.7033(5) 0.0465(14) Uani 1 1 d . . . . .
C18 C 0.2442(7) 0.4132(5) 0.8077(6) 0.0556(18) Uani 1 1 d . . . . .
C19 C 0.1481(6) 0.4015(4) 0.8503(6) 0.0500(17) Uani 1 1 d . . . . .
C20 C 0.1488(7) 0.3389(7) 0.9358(7) 0.081(3) Uani 1 1 d . . . . .
H20A H 0.1537 0.3762 0.9931 0.121 Uiso 1 1 calc GR . . . .
H20B H 0.2073 0.2974 0.9391 0.121 Uiso 1 1 calc GR . . . .
H20C H 0.0859 0.3030 0.9300 0.121 Uiso 1 1 calc GR . . . .
C21 C 0.4050(5) 0.2658(4) 0.7178(5) 0.0477(14) Uani 1 1 d . . . . .
H21A H 0.3685 0.2395 0.7677 0.057 Uiso 1 1 calc R . . . .
H21B H 0.3558 0.2690 0.6597 0.057 Uiso 1 1 calc R . . . .
C22 C 0.4903(6) 0.1983(5) 0.6998(6) 0.0601(18) Uani 1 1 d . . . . .
H22A H 0.5255 0.2214 0.6485 0.090 Uiso 1 1 calc GR . . . .
H22B H 0.4605 0.1382 0.6825 0.090 Uiso 1 1 calc GR . . . .
H22C H 0.5388 0.1923 0.7570 0.090 Uiso 1 1 calc GR . . . .
C23 C 0.3462(5) 0.4097(4) 0.8480(5) 0.0375(13) Uani 1 1 d . . . . .
C24 C 0.3728(6) 0.4296(6) 0.9532(5) 0.0552(16) Uani 1 1 d . . . . .
H24A H 0.4468 0.4294 0.9695 0.083 Uiso 1 1 calc GR . . . .
H24B H 0.3428 0.3822 0.9896 0.083 Uiso 1 1 calc GR . . . .
H24C H 0.3457 0.4897 0.9677 0.083 Uiso 1 1 calc GR . . . .
B1 B 0.6804(5) 0.4777(5) 0.7775(5) 0.0419(15) Uani 1 1 d . . . . .
H1 H 0.7527 0.4992 0.7857 0.050 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 O1 2.045(4) . ?
Ir1 N2 2.182(5) . ?
Ir1 N4 2.048(5) . ?
Ir1 N6 2.191(5) . ?
Ir1 C21 2.099(6) . ?
Ir1 C23 1.944(7) . ?
O1 C17 1.272(8) . ?
O2 C19 1.212(9) . ?
N1 N2 1.360(7) . ?
N1 C1 1.359(8) . ?
N1 B1 1.546(8) . ?
N2 C3 1.337(9) . ?
N3 N4 1.367(7) . ?
N3 C6 1.348(8) . ?
N3 B1 1.528(9) . ?
N4 C8 1.347(7) . ?
N5 N6 1.355(8) . ?
N5 C11 1.343(8) . ?
N5 B1 1.545(9) . ?
N6 C13 1.344(9) . ?
C1 C2 1.363(9) . ?
C1 C4 1.476(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(10) . ?
C3 C5 1.488(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.367(10) . ?
C6 C9 1.495(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(9) . ?
C8 C10 1.497(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.366(12) . ?
C11 C14 1.491(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(11) . ?
C13 C15 1.484(10) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C17 1.494(9) . ?
C17 C18 1.475(10) . ?
C18 C19 1.460(11) . ?
C18 C23 1.373(11) . ?
C19 C20 1.495(11) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.514(10) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.500(9) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
B1 H1 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
O1 Ir1 N2 94.41(18) . . ?
O1 Ir1 N4 176.50(17) . . ?
O1 Ir1 N6 94.69(19) . . ?
O1 Ir1 C21 84.6(2) . . ?
N2 Ir1 N6 82.12(18) . . ?
N4 Ir1 N2 88.43(19) . . ?
N4 Ir1 N6 87.7(2) . . ?
N4 Ir1 C21 92.9(2) . . ?
C21 Ir1 N2 172.3(2) . . ?
C21 Ir1 N6 90.4(2) . . ?
C23 Ir1 O1 80.1(2) . . ?
C23 Ir1 N2 95.1(2) . . ?
C23 Ir1 N4 97.6(3) . . ?
C23 Ir1 N6 173.9(2) . . ?
C23 Ir1 C21 92.2(2) . . ?
C17 O1 Ir1 112.7(4) . . ?
N2 N1 B1 120.0(5) . . ?
C1 N1 N2 109.5(5) . . ?
C1 N1 B1 130.1(5) . . ?
N1 N2 Ir1 116.8(4) . . ?
C3 N2 Ir1 135.5(4) . . ?
C3 N2 N1 107.1(5) . . ?
N4 N3 B1 120.7(5) . . ?
C6 N3 N4 109.4(5) . . ?
C6 N3 B1 129.7(5) . . ?
N3 N4 Ir1 118.9(4) . . ?
C8 N4 Ir1 134.0(4) . . ?
C8 N4 N3 107.1(5) . . ?
N6 N5 B1 119.3(5) . . ?
C11 N5 N6 110.6(5) . . ?
C11 N5 B1 129.4(6) . . ?
N5 N6 Ir1 117.0(4) . . ?
C13 N6 Ir1 135.9(5) . . ?
C13 N6 N5 107.2(6) . . ?
N1 C1 C2 107.7(5) . . ?
N1 C1 C4 122.8(6) . . ?
C2 C1 C4 129.5(6) . . ?
C1 C2 H2 126.8 . . ?
C1 C2 C3 106.3(6) . . ?
C3 C2 H2 126.8 . . ?
N2 C3 C2 109.3(6) . . ?
N2 C3 C5 122.7(6) . . ?
C2 C3 C5 127.8(6) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 107.5(6) . . ?
N3 C6 C9 122.4(6) . . ?
C7 C6 C9 130.2(6) . . ?
C6 C7 H7 126.3 . . ?
C6 C7 C8 107.4(6) . . ?
C8 C7 H7 126.3 . . ?
N4 C8 C7 108.7(6) . . ?
N4 C8 C10 124.8(6) . . ?
C7 C8 C10 126.5(6) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 C12 106.8(6) . . ?
N5 C11 C14 122.8(7) . . ?
C12 C11 C14 130.4(7) . . ?
C11 C12 H12 126.3 . . ?
C11 C12 C13 107.4(6) . . ?
C13 C12 H12 126.3 . . ?
N6 C13 C12 107.9(7) . . ?
N6 C13 C15 123.6(7) . . ?
C12 C13 C15 128.4(7) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
O1 C17 C16 116.3(6) . . ?
O1 C17 C18 117.6(6) . . ?
C18 C17 C16 125.7(7) . . ?
C19 C18 C17 117.7(7) . . ?
C23 C18 C17 111.2(7) . . ?
C23 C18 C19 131.0(7) . . ?
O2 C19 C18 123.8(7) . . ?
O2 C19 C20 117.5(7) . . ?
C18 C19 C20 118.6(7) . . ?
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 . . ?
Ir1 C21 H21A 107.9 . . ?
Ir1 C21 H21B 107.9 . . ?
H21A C21 H21B 107.2 . . ?
C22 C21 Ir1 117.8(5) . . ?
C22 C21 H21A 107.9 . . ?
C22 C21 H21B 107.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 Ir1 115.8(5) . . ?
C18 C23 C24 119.2(6) . . ?
C24 C23 Ir1 123.9(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 B1 H1 110.0 . . ?
N3 B1 N1 110.2(5) . . ?
N3 B1 N5 109.2(5) . . ?
N3 B1 H1 110.0 . . ?
N5 B1 N1 107.5(5) . . ?
N5 B1 H1 110.0 . . ?

_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_mm014m
_database_code_depnum_ccdc_archive 'CCDC 1400508'
_audit_update_record             
;
2015-05-12 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 B Br5 Ir N6 O2, C6 H14'
_chemical_formula_sum            'C26 H39 B Br5 Ir N6 O2'
_chemical_formula_weight         1070.19
_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'
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'
Br Br -0.2901 2.4595 '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'

_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                   11.8577(5)
_cell_length_b                   16.3125(7)
_cell_length_c                   18.7394(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.2370(10)
_cell_angle_gamma                90
_cell_volume                     3528.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.369
_cell_measurement_theta_min      2.239
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.479
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.3197
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1593 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.4292.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.015
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2040
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1536
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18079
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        23.283
_diffrn_reflns_theta_max         23.283
_diffrn_reflns_theta_min         1.675
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                3750
_reflns_number_total             5076
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.353
_refine_diff_density_min         -1.453
_refine_diff_density_rms         0.234
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         5076
_refine_ls_number_restraints     393
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      0.958
_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)+(0.1029P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C22-C23 = C23-C24 = C24-C25 = C25-C26 = C26-C27
 1.54 with sigma of 0.01
 C22-C24 = C23-C25 = C24-C26 = C25-C27
 2.5 with sigma of 0.01
 N1-C1 \\sim N2-C3 \\sim N1-C1A \\sim N2-C3A
 with sigma of 0.01
3. Restrained planarity
 N1, N2, C1, C2, C3, C4, C5, Br1
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C22A \\sim C23A
\\sim C24A \\sim C25A \\sim C26A \\sim C27A: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.02
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim Br1 \\sim C1A \\sim C2A \\sim C3A
\\sim C12A \\sim C5A \\sim Br1A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C22, C23, C24, C25, C26, C27, C22A, C23A, C24A, C25A, C26A, C27A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C1, C2, C3, C4, C5, Br1, C1A, C2A, C3A, C12A, C5A, Br1A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
6. Same fragment restrains
{C1, C2, C3, C4, C5, Br1} sigma for 1-2: 0.02, 1-3: 0.04
as
{C1A, C2A, C3A, C12A, C5A, Br1A}
{C22, C23, C24, C25, C26, C27} sigma for 1-2: 0.02, 1-3: 0.04
as
{C22A, C23A, C24A, C25A, C26A, C27A}
7. Others
 Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C23A)=Sof(H23C)=Sof(H23D)=
 Sof(C24A)=Sof(H24C)=Sof(H24D)=Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C26A)=
 Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=
 Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C5A)=
 Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=Sof(Br1A)=1-FVAR(2)
 Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=Sof(C5)=Sof(H5A)=
 Sof(H5B)=Sof(H5C)=Sof(Br1)=FVAR(2)
8.a Ternary CH refined with riding coordinates:
 B1(H1)
8.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C23A(H23C,
 H23D), C24A(H24C,H24D), C25A(H25C,H25D), C26A(H26C,H26D)
8.c Me refined with riding coordinates:
 C22(H22A,H22B,H22C), C27(H27A,H27B,H27C), C22A(H22D,H22E,H22F), C27A(H27D,
 H27E,H27F)
8.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C9(H9A,H9B,H9C), C10(H10A,H10B,
 H10C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C12A(H12A,H12B,H12C), C5A(H5AA,H5AB,
 H5AC), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C)
;
_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 0.14725(4) 0.15049(2) 0.23739(2) 0.0379(2) Uani 1 1 d . . . . .
Br2 Br -0.12955(15) 0.33784(10) -0.01837(8) 0.0772(5) Uani 1 1 d . . . . .
Br5 Br -0.04094(13) 0.11609(9) 0.26664(8) 0.0644(4) Uani 1 1 d . . . . .
Br4 Br 0.11683(15) -0.16541(8) 0.23781(10) 0.0714(5) Uani 1 1 d . . . . .
O2 O 0.1212(7) 0.0654(4) 0.1563(4) 0.047(2) Uani 1 1 d . . . . .
O1 O 0.2251(8) 0.0647(5) 0.3115(4) 0.053(2) Uani 1 1 d . . . . .
N5 N 0.2107(9) 0.3154(5) 0.2993(5) 0.044(2) Uani 1 1 d . . . . .
N6 N 0.1781(9) 0.2374(5) 0.3172(5) 0.049(3) Uani 1 1 d . . . . .
B1 B 0.2338(12) 0.3273(7) 0.2234(8) 0.042(3) Uani 1 1 d . . . . .
H1 H 0.2610 0.3834 0.2187 0.051 Uiso 1 1 calc R . . . .
N3 N 0.1234(9) 0.3118(5) 0.1650(5) 0.045(2) Uani 1 1 d . . . . .
N4 N 0.0690(9) 0.2345(6) 0.1620(5) 0.047(2) Uani 1 1 d . . . . .
C14 C 0.2526(15) 0.4544(7) 0.3551(7) 0.070(4) Uani 1 1 d . . . . .
H14A H 0.2201 0.4838 0.3899 0.105 Uiso 1 1 calc GR . . . .
H14B H 0.2209 0.4752 0.3067 0.105 Uiso 1 1 calc GR . . . .
H14C H 0.3352 0.4612 0.3668 0.105 Uiso 1 1 calc GR . . . .
C11 C 0.2237(11) 0.3647(7) 0.3578(6) 0.045(3) Uani 1 1 d . . . . .
C12 C 0.2065(12) 0.3181(8) 0.4141(7) 0.057(3) Uani 1 1 d . . . . .
C13 C 0.1770(11) 0.2376(7) 0.3898(6) 0.046(3) Uani 1 1 d . . . . .
C15 C 0.1564(15) 0.1652(8) 0.4325(7) 0.070(4) Uani 1 1 d . . . . .
H15A H 0.1884 0.1749 0.4836 0.105 Uiso 1 1 calc GR . . . .
H15B H 0.1928 0.1181 0.4168 0.105 Uiso 1 1 calc GR . . . .
H15C H 0.0746 0.1557 0.4247 0.105 Uiso 1 1 calc GR . . . .
Br3 Br 0.21472(17) 0.35196(10) 0.51185(8) 0.0808(5) Uani 1 1 d . . . . .
C9 C 0.0968(14) 0.4427(7) 0.0942(7) 0.067(4) Uani 1 1 d . . . . .
H9A H 0.0899 0.4521 0.0428 0.100 Uiso 1 1 calc GR . . . .
H9B H 0.1754 0.4522 0.1202 0.100 Uiso 1 1 calc GR . . . .
H9C H 0.0462 0.4794 0.1120 0.100 Uiso 1 1 calc GR . . . .
C6 C 0.0645(12) 0.3575(7) 0.1058(7) 0.048(3) Uani 1 1 d . . . . .
C7 C -0.0234(11) 0.3082(8) 0.0693(7) 0.052(3) Uani 1 1 d . . . . .
C8 C -0.0185(11) 0.2343(7) 0.1031(6) 0.045(3) Uani 1 1 d . . . . .
C10 C -0.0984(13) 0.1626(8) 0.0833(8) 0.069(4) Uani 1 1 d . . . . .
H10A H -0.1704 0.1807 0.0527 0.104 Uiso 1 1 calc GR . . . .
H10B H -0.1125 0.1384 0.1272 0.104 Uiso 1 1 calc GR . . . .
H10C H -0.0635 0.1227 0.0574 0.104 Uiso 1 1 calc GR . . . .
N1 N 0.3280(9) 0.2651(5) 0.2128(4) 0.053(3) Uani 1 1 d D . . . .
N2 N 0.3058(8) 0.1825(5) 0.2150(4) 0.045(2) Uani 1 1 d D . . . .
C1 C 0.4363(11) 0.2735(11) 0.2074(5) 0.051(3) Uani 0.70(4) 1 d D U P A 1
C2 C 0.4850(13) 0.1954(12) 0.2059(6) 0.051(3) Uani 0.70(4) 1 d D U P A 1
C3 C 0.3982(11) 0.1399(10) 0.2109(6) 0.048(3) Uani 0.70(4) 1 d D U P A 1
C4 C 0.497(2) 0.3529(12) 0.2034(9) 0.062(5) Uani 0.70(4) 1 d D U P A 1
H4A H 0.5767 0.3478 0.2282 0.093 Uiso 0.70(4) 1 calc GR . P A 1
H4B H 0.4609 0.3951 0.2265 0.093 Uiso 0.70(4) 1 calc GR . P A 1
H4C H 0.4912 0.3671 0.1530 0.093 Uiso 0.70(4) 1 calc GR . P A 1
C5 C 0.407(2) 0.0489(11) 0.2116(9) 0.054(5) Uani 0.70(4) 1 d D U P A 1
H5A H 0.4757 0.0330 0.1958 0.082 Uiso 0.70(4) 1 calc GR . P A 1
H5B H 0.3403 0.0260 0.1792 0.082 Uiso 0.70(4) 1 calc GR . P A 1
H5C H 0.4123 0.0290 0.2605 0.082 Uiso 0.70(4) 1 calc GR . P A 1
Br1 Br 0.6358(8) 0.1714(7) 0.1988(11) 0.101(3) Uani 0.70(4) 1 d D U P A 1
C1A C 0.420(3) 0.281(2) 0.187(3) 0.051(4) Uani 0.30(4) 1 d D U P A 2
C2A C 0.470(3) 0.204(2) 0.184(3) 0.050(3) Uani 0.30(4) 1 d D U P A 2
C3A C 0.395(3) 0.1446(18) 0.200(3) 0.048(4) Uani 0.30(4) 1 d D U P A 2
C12A C 0.463(5) 0.364(2) 0.177(4) 0.059(7) Uani 0.30(4) 1 d D U P A 2
H12A H 0.5335 0.3604 0.1598 0.089 Uiso 0.30(4) 1 calc GR . P A 2
H12B H 0.4789 0.3928 0.2231 0.089 Uiso 0.30(4) 1 calc GR . P A 2
H12C H 0.4062 0.3939 0.1419 0.089 Uiso 0.30(4) 1 calc GR . P A 2
C5A C 0.394(6) 0.055(2) 0.188(4) 0.049(6) Uani 0.30(4) 1 d D U P A 2
H5AA H 0.4678 0.0378 0.1791 0.074 Uiso 0.30(4) 1 calc GR . P A 2
H5AB H 0.3339 0.0406 0.1460 0.074 Uiso 0.30(4) 1 calc GR . P A 2
H5AC H 0.3812 0.0270 0.2303 0.074 Uiso 0.30(4) 1 calc GR . P A 2
Br1A Br 0.617(2) 0.1806(18) 0.1710(19) 0.106(6) Uani 0.30(4) 1 d D U P A 2
C20 C 0.0819(14) -0.0600(8) 0.0973(7) 0.067(4) Uani 1 1 d . . . . .
H20A H 0.1292 -0.1082 0.1004 0.101 Uiso 1 1 calc GR . . . .
H20B H 0.0925 -0.0264 0.0573 0.101 Uiso 1 1 calc GR . . . .
H20C H 0.0019 -0.0758 0.0894 0.101 Uiso 1 1 calc GR . . . .
C19 C 0.1162(10) -0.0124(7) 0.1678(7) 0.044(3) Uani 1 1 d . . . . .
C18 C 0.1450(9) -0.0494(7) 0.2354(6) 0.042(3) Uani 1 1 d . . . . .
C17 C 0.2019(11) -0.0139(6) 0.3018(7) 0.046(3) Uani 1 1 d . . . . .
C16 C 0.2434(13) -0.0613(8) 0.3701(8) 0.069(4) Uani 1 1 d . . . . .
H16A H 0.2842 -0.1091 0.3598 0.104 Uiso 1 1 calc GR . . . .
H16B H 0.1785 -0.0778 0.3893 0.104 Uiso 1 1 calc GR . . . .
H16C H 0.2945 -0.0279 0.4055 0.104 Uiso 1 1 calc GR . . . .
C22 C 0.603(5) 0.400(3) 0.469(3) 0.307(18) Uani 0.69(2) 1 d D U P B 1
H22A H 0.6244 0.4479 0.4451 0.461 Uiso 0.69(2) 1 calc R . P B 1
H22B H 0.5395 0.4134 0.4907 0.461 Uiso 0.69(2) 1 calc R . P B 1
H22C H 0.6683 0.3830 0.5069 0.461 Uiso 0.69(2) 1 calc R . P B 1
C23 C 0.568(6) 0.330(3) 0.413(2) 0.304(17) Uani 0.69(2) 1 d D U P B 1
H23A H 0.5025 0.3472 0.3744 0.364 Uiso 0.69(2) 1 calc R . P B 1
H23B H 0.6318 0.3167 0.3907 0.364 Uiso 0.69(2) 1 calc R . P B 1
C24 C 0.535(7) 0.256(3) 0.454(2) 0.303(17) Uani 0.69(2) 1 d D U P B 1
H24A H 0.5999 0.2399 0.4933 0.364 Uiso 0.69(2) 1 calc R . P B 1
H24B H 0.4701 0.2691 0.4752 0.364 Uiso 0.69(2) 1 calc R . P B 1
C25 C 0.502(6) 0.185(3) 0.399(2) 0.304(17) Uani 0.69(2) 1 d D U P B 1
H25A H 0.5636 0.1756 0.3736 0.365 Uiso 0.69(2) 1 calc R . P B 1
H25B H 0.4317 0.1977 0.3634 0.365 Uiso 0.69(2) 1 calc R . P B 1
C26 C 0.484(5) 0.107(3) 0.442(3) 0.304(17) Uani 0.69(2) 1 d D U P B 1
H26A H 0.5091 0.1172 0.4945 0.365 Uiso 0.69(2) 1 calc R . P B 1
H26B H 0.4030 0.0923 0.4311 0.365 Uiso 0.69(2) 1 calc R . P B 1
C27 C 0.556(5) 0.037(3) 0.420(3) 0.310(18) Uani 0.69(2) 1 d D U P B 1
H27A H 0.5461 -0.0117 0.4463 0.465 Uiso 0.69(2) 1 calc R . P B 1
H27B H 0.5310 0.0274 0.3682 0.465 Uiso 0.69(2) 1 calc R . P B 1
H27C H 0.6367 0.0523 0.4314 0.465 Uiso 0.69(2) 1 calc R . P B 1
C22A C 0.536(13) 0.362(8) 0.454(6) 0.305(18) Uani 0.31(2) 1 d D U P B 2
H22D H 0.5481 0.4202 0.4551 0.457 Uiso 0.31(2) 1 calc R . P B 2
H22E H 0.5944 0.3359 0.4337 0.457 Uiso 0.31(2) 1 calc R . P B 2
H22F H 0.4608 0.3501 0.4231 0.457 Uiso 0.31(2) 1 calc R . P B 2
C23A C 0.542(12) 0.329(8) 0.533(5) 0.306(18) Uani 0.31(2) 1 d D U P B 2
H23C H 0.6178 0.3397 0.5645 0.367 Uiso 0.31(2) 1 calc R . P B 2
H23D H 0.4831 0.3540 0.5539 0.367 Uiso 0.31(2) 1 calc R . P B 2
C24A C 0.521(11) 0.236(8) 0.519(4) 0.305(17) Uani 0.31(2) 1 d D U P B 2
H24C H 0.5815 0.2039 0.5501 0.366 Uiso 0.31(2) 1 calc R . P B 2
H24D H 0.4467 0.2199 0.5283 0.366 Uiso 0.31(2) 1 calc R . P B 2
C25A C 0.522(17) 0.224(7) 0.437(4) 0.304(17) Uani 0.31(2) 1 d D U P B 2
H25C H 0.4516 0.2469 0.4066 0.365 Uiso 0.31(2) 1 calc R . P B 2
H25D H 0.5877 0.2522 0.4263 0.365 Uiso 0.31(2) 1 calc R . P B 2
C26A C 0.529(12) 0.132(7) 0.424(7) 0.304(17) Uani 0.31(2) 1 d D U P B 2
H26C H 0.4522 0.1092 0.4041 0.365 Uiso 0.31(2) 1 calc R . P B 2
H26D H 0.5635 0.1032 0.4687 0.365 Uiso 0.31(2) 1 calc R . P B 2
C27A C 0.605(10) 0.122(9) 0.367(7) 0.306(19) Uani 0.31(2) 1 d D U P B 2
H27D H 0.6120 0.0647 0.3567 0.459 Uiso 0.31(2) 1 calc R . P B 2
H27E H 0.5696 0.1503 0.3230 0.459 Uiso 0.31(2) 1 calc R . P B 2
H27F H 0.6803 0.1443 0.3872 0.459 Uiso 0.31(2) 1 calc R . 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 Br5 2.4809(15) . ?
Ir1 O2 2.028(7) . ?
Ir1 O1 2.038(8) . ?
Ir1 N6 2.032(10) . ?
Ir1 N4 2.033(10) . ?
Ir1 N2 2.085(9) . ?
Br2 C7 1.889(12) . ?
Br4 C18 1.924(11) . ?
O2 C19 1.292(12) . ?
O1 C17 1.316(13) . ?
N5 N6 1.394(12) . ?
N5 B1 1.520(17) . ?
N5 C11 1.339(15) . ?
N6 C13 1.363(14) . ?
B1 H1 0.9800 . ?
B1 N3 1.524(17) . ?
B1 N1 1.556(16) . ?
N3 N4 1.412(13) . ?
N3 C6 1.385(15) . ?
N4 C8 1.330(15) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C11 1.507(16) . ?
C11 C12 1.352(18) . ?
C12 C13 1.407(17) . ?
C12 Br3 1.895(12) . ?
C13 C15 1.478(17) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C6 1.471(16) . ?
C6 C7 1.368(18) . ?
C7 C8 1.358(16) . ?
C8 C10 1.497(17) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 N2 1.374(12) . ?
N1 C1 1.319(12) . ?
N1 C1A 1.314(14) . ?
N2 C3 1.314(12) . ?
N2 C3A 1.312(13) . ?
C1 C2 1.403(19) . ?
C1 C4 1.490(18) . ?
C2 C3 1.390(18) . ?
C2 Br1 1.864(14) . ?
C3 C5 1.488(17) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C1A C2A 1.40(2) . ?
C1A C12A 1.49(2) . ?
C2A C3A 1.39(2) . ?
C2A Br1A 1.858(19) . ?
C3A C5A 1.49(2) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C5A H5AA 0.9600 . ?
C5A H5AB 0.9600 . ?
C5A H5AC 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C19 1.505(16) . ?
C19 C18 1.375(16) . ?
C18 C17 1.397(17) . ?
C17 C16 1.480(18) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 C23 1.546(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.539(10) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.536(10) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.540(10) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.538(10) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C22A C23A 1.56(2) . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?
C23A C24A 1.56(2) . ?
C24A H24C 0.9700 . ?
C24A H24D 0.9700 . ?
C24A C25A 1.54(2) . ?
C25A H25C 0.9700 . ?
C25A H25D 0.9700 . ?
C25A C26A 1.54(2) . ?
C26A H26C 0.9700 . ?
C26A H26D 0.9700 . ?
C26A C27A 1.54(2) . ?
C27A H27D 0.9600 . ?
C27A H27E 0.9600 . ?
C27A H27F 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
O2 Ir1 Br5 91.2(2) . . ?
O2 Ir1 O1 90.5(3) . . ?
O2 Ir1 N6 178.0(3) . . ?
O2 Ir1 N4 88.5(3) . . ?
O2 Ir1 N2 90.6(3) . . ?
O1 Ir1 Br5 89.1(2) . . ?
O1 Ir1 N2 91.2(3) . . ?
N6 Ir1 Br5 90.8(3) . . ?
N6 Ir1 O1 90.0(4) . . ?
N6 Ir1 N4 91.0(4) . . ?
N6 Ir1 N2 87.4(4) . . ?
N4 Ir1 Br5 90.9(3) . . ?
N4 Ir1 O1 179.0(4) . . ?
N4 Ir1 N2 88.9(4) . . ?
N2 Ir1 Br5 178.2(2) . . ?
C19 O2 Ir1 123.6(7) . . ?
C17 O1 Ir1 121.8(8) . . ?
N6 N5 B1 117.4(9) . . ?
C11 N5 N6 109.7(9) . . ?
C11 N5 B1 132.6(10) . . ?
N5 N6 Ir1 118.3(7) . . ?
C13 N6 Ir1 134.1(8) . . ?
C13 N6 N5 107.7(9) . . ?
N5 B1 H1 109.7 . . ?
N5 B1 N3 110.0(10) . . ?
N5 B1 N1 108.9(9) . . ?
N3 B1 H1 109.7 . . ?
N3 B1 N1 108.9(9) . . ?
N1 B1 H1 109.7 . . ?
N4 N3 B1 119.1(9) . . ?
C6 N3 B1 132.8(10) . . ?
C6 N3 N4 107.9(10) . . ?
N3 N4 Ir1 116.3(8) . . ?
C8 N4 Ir1 136.0(8) . . ?
C8 N4 N3 107.3(9) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
N5 C11 C14 122.6(11) . . ?
N5 C11 C12 107.0(10) . . ?
C12 C11 C14 130.4(11) . . ?
C11 C12 C13 110.0(11) . . ?
C11 C12 Br3 127.4(10) . . ?
C13 C12 Br3 122.6(10) . . ?
N6 C13 C12 105.5(10) . . ?
N6 C13 C15 125.3(11) . . ?
C12 C13 C15 129.1(11) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
N3 C6 C9 121.7(12) . . ?
C7 C6 N3 105.7(10) . . ?
C7 C6 C9 132.5(12) . . ?
C6 C7 Br2 124.3(9) . . ?
C8 C7 Br2 125.6(10) . . ?
C8 C7 C6 110.0(11) . . ?
N4 C8 C7 109.1(11) . . ?
N4 C8 C10 122.5(11) . . ?
C7 C8 C10 128.4(12) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 N1 B1 119.2(8) . . ?
C1 N1 B1 133.0(11) . . ?
C1 N1 N2 107.5(11) . . ?
C1A N1 B1 126.8(17) . . ?
C1A N1 N2 112.4(16) . . ?
N1 N2 Ir1 116.0(6) . . ?
C3 N2 Ir1 132.9(10) . . ?
C3 N2 N1 110.5(11) . . ?
C3A N2 Ir1 137.3(16) . . ?
C3A N2 N1 106.7(16) . . ?
N1 C1 C2 108.6(12) . . ?
N1 C1 C4 125.6(15) . . ?
C2 C1 C4 125.8(14) . . ?
C1 C2 Br1 126.7(11) . . ?
C3 C2 C1 106.0(13) . . ?
C3 C2 Br1 127.3(11) . . ?
N2 C3 C2 107.4(12) . . ?
N2 C3 C5 126.1(16) . . ?
C2 C3 C5 126.5(14) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C1A C2A 103.6(18) . . ?
N1 C1A C12A 125(3) . . ?
C2A C1A C12A 131(2) . . ?
C1A C2A Br1A 127.6(19) . . ?
C3A C2A C1A 108.6(19) . . ?
C3A C2A Br1A 123.6(19) . . ?
N2 C3A C2A 107.7(19) . . ?
N2 C3A C5A 122(3) . . ?
C2A C3A C5A 130(3) . . ?
C1A C12A H12A 109.5 . . ?
C1A C12A H12B 109.5 . . ?
C1A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C3A C5A H5AA 109.5 . . ?
C3A C5A H5AB 109.5 . . ?
C3A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
O2 C19 C20 112.0(11) . . ?
O2 C19 C18 125.0(11) . . ?
C18 C19 C20 122.8(10) . . ?
C19 C18 Br4 116.5(8) . . ?
C19 C18 C17 127.3(10) . . ?
C17 C18 Br4 116.0(8) . . ?
O1 C17 C18 124.8(11) . . ?
O1 C17 C16 111.8(12) . . ?
C18 C17 C16 123.4(10) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
C22 C23 H23A 110.2 . . ?
C22 C23 H23B 110.2 . . ?
H23A C23 H23B 108.5 . . ?
C24 C23 C22 107.6(10) . . ?
C24 C23 H23A 110.2 . . ?
C24 C23 H23B 110.2 . . ?
C23 C24 H24A 110.0 . . ?
C23 C24 H24B 110.0 . . ?
H24A C24 H24B 108.4 . . ?
C25 C24 C23 108.5(10) . . ?
C25 C24 H24A 110.0 . . ?
C25 C24 H24B 110.0 . . ?
C24 C25 H25A 110.0 . . ?
C24 C25 H25B 110.0 . . ?
C24 C25 C26 108.3(10) . . ?
H25A C25 H25B 108.4 . . ?
C26 C25 H25A 110.0 . . ?
C26 C25 H25B 110.0 . . ?
C25 C26 H26A 110.0 . . ?
C25 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?
C27 C26 C25 108.4(10) . . ?
C27 C26 H26A 110.0 . . ?
C27 C26 H26B 110.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C23A C22A H22D 109.5 . . ?
C23A C22A H22E 109.5 . . ?
C23A C22A H22F 109.5 . . ?
C22A C23A H23C 111.4 . . ?
C22A C23A H23D 111.4 . . ?
H23C C23A H23D 109.2 . . ?
C24A C23A C22A 102(3) . . ?
C24A C23A H23C 111.4 . . ?
C24A C23A H23D 111.4 . . ?
C23A C24A H24C 110.9 . . ?
C23A C24A H24D 110.9 . . ?
H24C C24A H24D 108.9 . . ?
C25A C24A C23A 104(3) . . ?
C25A C24A H24C 110.9 . . ?
C25A C24A H24D 110.9 . . ?
C24A C25A H25C 110.2 . . ?
C24A C25A H25D 110.2 . . ?
H25C C25A H25D 108.5 . . ?
C26A C25A C24A 108(3) . . ?
C26A C25A H25C 110.2 . . ?
C26A C25A H25D 110.2 . . ?
C25A C26A H26C 110.5 . . ?
C25A C26A H26D 110.5 . . ?
C25A C26A C27A 106(3) . . ?
H26C C26A H26D 108.7 . . ?
C27A C26A H26C 110.5 . . ?
C27A C26A H26D 110.5 . . ?
C26A C27A H27D 109.5 . . ?
C26A C27A H27E 109.5 . . ?
C26A C27A H27F 109.5 . . ?
H27D C27A H27E 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ir1 O2 C19 C20 173.1(8) . . . . ?
Ir1 O2 C19 C18 -10.5(16) . . . . ?
Ir1 O1 C17 C18 15.1(15) . . . . ?
Ir1 O1 C17 C16 -164.9(8) . . . . ?
Ir1 N6 C13 C12 179.9(9) . . . . ?
Ir1 N6 C13 C15 4(2) . . . . ?
Ir1 N4 C8 C7 -173.4(9) . . . . ?
Ir1 N4 C8 C10 9.3(19) . . . . ?
Ir1 N2 C3 C2 -170.5(6) . . . . ?
Ir1 N2 C3 C5 9.5(7) . . . . ?
Ir1 N2 C3A C2A 175(3) . . . . ?
Ir1 N2 C3A C5A 6(7) . . . . ?
Br2 C7 C8 N4 178.1(9) . . . . ?
Br2 C7 C8 C10 -4.9(19) . . . . ?
Br4 C18 C17 O1 -177.6(9) . . . . ?
Br4 C18 C17 C16 2.4(16) . . . . ?
O2 C19 C18 Br4 174.7(9) . . . . ?
O2 C19 C18 C17 -11.4(19) . . . . ?
N5 N6 C13 C12 1.6(13) . . . . ?
N5 N6 C13 C15 -174.7(12) . . . . ?
N5 B1 N3 N4 -59.1(13) . . . . ?
N5 B1 N3 C6 127.5(13) . . . . ?
N5 B1 N1 N2 62.0(11) . . . . ?
N5 B1 N1 C1 -111.3(9) . . . . ?
N5 B1 N1 C1A -133(4) . . . . ?
N5 C11 C12 C13 -2.5(15) . . . . ?
N5 C11 C12 Br3 179.2(10) . . . . ?
N6 N5 B1 N3 63.1(13) . . . . ?
N6 N5 B1 N1 -56.1(13) . . . . ?
N6 N5 C11 C14 -176.7(12) . . . . ?
N6 N5 C11 C12 3.5(14) . . . . ?
B1 N5 N6 Ir1 -6.6(13) . . . . ?
B1 N5 N6 C13 172.1(10) . . . . ?
B1 N5 C11 C14 9(2) . . . . ?
B1 N5 C11 C12 -170.8(13) . . . . ?
B1 N3 N4 Ir1 -0.6(13) . . . . ?
B1 N3 N4 C8 -174.7(10) . . . . ?
B1 N3 C6 C9 -8(2) . . . . ?
B1 N3 C6 C7 174.6(12) . . . . ?
B1 N1 N2 Ir1 -2.7(8) . . . . ?
B1 N1 N2 C3 -174.9(8) . . . . ?
B1 N1 N2 C3A 176(3) . . . . ?
B1 N1 C1 C2 173.9(10) . . . . ?
B1 N1 C1 C4 -6.1(10) . . . . ?
B1 N1 C1A C2A -176(2) . . . . ?
B1 N1 C1A C12A 13(7) . . . . ?
N3 B1 N1 N2 -57.9(11) . . . . ?
N3 B1 N1 C1 128.7(8) . . . . ?
N3 B1 N1 C1A 107(4) . . . . ?
N3 N4 C8 C7 -1.1(13) . . . . ?
N3 N4 C8 C10 -178.3(11) . . . . ?
N3 C6 C7 Br2 -177.9(9) . . . . ?
N3 C6 C7 C8 -1.3(14) . . . . ?
N4 N3 C6 C9 177.7(11) . . . . ?
N4 N3 C6 C7 0.7(13) . . . . ?
C14 C11 C12 C13 177.7(13) . . . . ?
C14 C11 C12 Br3 -1(2) . . . . ?
C11 N5 N6 Ir1 178.1(8) . . . . ?
C11 N5 N6 C13 -3.3(13) . . . . ?
C11 N5 B1 N3 -122.8(13) . . . . ?
C11 N5 B1 N1 117.9(13) . . . . ?
C11 C12 C13 N6 0.5(15) . . . . ?
C11 C12 C13 C15 176.6(14) . . . . ?
Br3 C12 C13 N6 178.9(9) . . . . ?
Br3 C12 C13 C15 -5(2) . . . . ?
C9 C6 C7 Br2 5(2) . . . . ?
C9 C6 C7 C8 -178.0(13) . . . . ?
C6 N3 N4 Ir1 174.3(7) . . . . ?
C6 N3 N4 C8 0.2(12) . . . . ?
C6 C7 C8 N4 1.5(14) . . . . ?
C6 C7 C8 C10 178.6(12) . . . . ?
N1 B1 N3 N4 60.2(13) . . . . ?
N1 B1 N3 C6 -113.2(13) . . . . ?
N1 N2 C3 C2 0.0(3) . . . . ?
N1 N2 C3 C5 180.0(2) . . . . ?
N1 N2 C3A C2A -3(4) . . . . ?
N1 N2 C3A C5A -172(4) . . . . ?
N1 C1 C2 C3 0.0(2) . . . . ?
N1 C1 C2 Br1 -179.9(2) . . . . ?
N1 C1A C2A C3A 8(5) . . . . ?
N1 C1A C2A Br1A -166(4) . . . . ?
N2 N1 C1 C2 0.03(13) . . . . ?
N2 N1 C1 C4 180.00(14) . . . . ?
N2 N1 C1A C2A -10(4) . . . . ?
N2 N1 C1A C12A 179(4) . . . . ?
C1 N1 N2 Ir1 172.2(5) . . . . ?
C1 N1 N2 C3 -0.01(14) . . . . ?
C1 C2 C3 N2 0.0(3) . . . . ?
C1 C2 C3 C5 -180.0(3) . . . . ?
C4 C1 C2 C3 180.0(2) . . . . ?
C4 C1 C2 Br1 0.1(3) . . . . ?
Br1 C2 C3 N2 179.9(2) . . . . ?
Br1 C2 C3 C5 0.0(5) . . . . ?
C1A N1 N2 Ir1 -169(3) . . . . ?
C1A N1 N2 C3A 9(4) . . . . ?
C1A C2A C3A N2 -3(5) . . . . ?
C1A C2A C3A C5A 165(5) . . . . ?
C12A C1A C2A C3A 178(5) . . . . ?
C12A C1A C2A Br1A 3(8) . . . . ?
Br1A C2A C3A N2 172(4) . . . . ?
Br1A C2A C3A C5A -20(8) . . . . ?
C20 C19 C18 Br4 -9.3(15) . . . . ?
C20 C19 C18 C17 164.6(12) . . . . ?
C19 C18 C17 O1 8.6(19) . . . . ?
C19 C18 C17 C16 -171.4(12) . . . . ?
C22 C23 C24 C25 -179(5) . . . . ?
C23 C24 C25 C26 173(6) . . . . ?
C24 C25 C26 C27 -129(6) . . . . ?
C22A C23A C24A C25A 8(14) . . . . ?
C23A C24A C25A C26A 167(13) . . . . ?
C24A C25A C26A C27A -144(11) . . . . ?

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