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

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

data_shelx
_audit_block_doi                 10.5517/cc13hqt4
_database_code_depnum_ccdc_archive 'CCDC 1028016'
_audit_update_record             
;
2014-10-07 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H36 Br Cl4 Ir N2'
_chemical_formula_weight         898.57

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   11.51870(10)
_cell_length_b                   12.8279(2)
_cell_length_c                   23.1283(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.5290(10)
_cell_angle_gamma                90
_cell_volume                     3395.29(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    15227
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    5.452
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.46020
_exptl_absorpt_correction_T_max  0.75595
_exptl_absorpt_process_details   'Alcock(1970) crystallographic computing,p271'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD Saphire 3 Xcalibur'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1852
_diffrn_reflns_number            26738
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.027
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7396
_reflns_number_gt                6314
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.35.11'
_computing_cell_refinement       
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.35.11'
_computing_data_reduction        
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.35.11'

_computing_structure_solution    'SIR-97_(Altomare & al., 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.3(CCDC, 2014)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+2.0046P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7396
_refine_ls_number_parameters     393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2461(3) 0.01050(18) 0.46569(9) 0.0809(7) Uani 1 1 d . . . . .
Cl2 Cl 0.2599(2) -0.21378(18) 0.47332(10) 0.0800(7) Uani 1 1 d . . . . .
C41 C 0.2257(7) -0.1075(6) 0.4290(3) 0.0515(19) Uani 1 1 d . . . . .
H41A H 0.1431 -0.1129 0.4119 0.062 Uiso 1 1 calc R U . . .
H41B H 0.2749 -0.1087 0.3966 0.062 Uiso 1 1 calc R U . . .
Cl3 Cl -0.4417(2) 0.20763(19) 0.37573(13) 0.0878(8) Uani 1 1 d . . . . .
Cl4 Cl -0.4345(2) -0.01671(18) 0.38710(13) 0.0943(9) Uani 1 1 d . . . . .
C42 C -0.5088(8) 0.0979(6) 0.3959(6) 0.094(4) Uani 1 1 d . . . . .
H42A H -0.5867 0.0932 0.3730 0.113 Uiso 1 1 calc R U . . .
H42B H -0.5213 0.1045 0.4374 0.113 Uiso 1 1 calc R U . . .
Ir1 Ir 0.03111(2) 0.08630(2) 0.27541(2) 0.01570(8) Uani 1 1 d . . . . .
Br1 Br 0.24399(5) 0.02729(5) 0.28277(3) 0.03149(15) Uani 1 1 d . . . . .
N1 N -0.0086(4) 0.1309(3) 0.39861(17) 0.0178(9) Uani 1 1 d . . . . .
N2 N 0.1322(4) 0.2269(3) 0.37605(19) 0.0240(10) Uani 1 1 d . . . . .
C1 C 0.0015(5) 0.0758(4) 0.1777(2) 0.0230(12) Uani 1 1 d . . . . .
C2 C 0.0334(4) 0.1836(4) 0.1940(2) 0.0204(11) Uani 1 1 d . . . . .
C3 C -0.0506(5) 0.2232(4) 0.2274(2) 0.0250(12) Uani 1 1 d . . . . .
C4 C -0.1349(5) 0.1414(5) 0.2351(2) 0.0306(13) Uani 1 1 d . . . . .
C5 C -0.1040(5) 0.0516(5) 0.2019(2) 0.0287(13) Uani 1 1 d . . . . .
C6 C 0.0643(6) 0.0088(5) 0.1402(2) 0.0395(15) Uani 1 1 d . . . . .
H6A H 0.1479 0.0093 0.1541 0.059 Uiso 1 1 calc R U . . .
H6B H 0.0525 0.0351 0.1001 0.059 Uiso 1 1 calc R U . . .
H6C H 0.0343 -0.0626 0.1412 0.059 Uiso 1 1 calc R U . . .
C7 C 0.1339(5) 0.2386(5) 0.1729(3) 0.0375(15) Uani 1 1 d . . . . .
H7A H 0.2014 0.1917 0.1753 0.056 Uiso 1 1 calc R U . . .
H7B H 0.1536 0.3002 0.1972 0.056 Uiso 1 1 calc R U . . .
H7C H 0.1131 0.2603 0.1325 0.056 Uiso 1 1 calc R U . . .
C8 C -0.0563(6) 0.3329(5) 0.2504(3) 0.0482(19) Uani 1 1 d . . . . .
H8A H -0.0735 0.3308 0.2909 0.072 Uiso 1 1 calc R U . . .
H8B H -0.1180 0.3716 0.2268 0.072 Uiso 1 1 calc R U . . .
H8C H 0.0189 0.3676 0.2485 0.072 Uiso 1 1 calc R U . . .
C9 C -0.2460(5) 0.1568(6) 0.2613(3) 0.054(2) Uani 1 1 d . . . . .
H9A H -0.2322 0.2038 0.2948 0.081 Uiso 1 1 calc R U . . .
H9B H -0.2741 0.0895 0.2741 0.081 Uiso 1 1 calc R U . . .
H9C H -0.3049 0.1874 0.2323 0.081 Uiso 1 1 calc R U . . .
C10 C -0.1718(6) -0.0462(6) 0.1932(3) 0.0512(19) Uani 1 1 d . . . . .
H10A H -0.2063 -0.0633 0.2289 0.077 Uiso 1 1 calc R U . . .
H10B H -0.1200 -0.1029 0.1840 0.077 Uiso 1 1 calc R U . . .
H10C H -0.2342 -0.0372 0.1611 0.077 Uiso 1 1 calc R U . . .
C11 C -0.0053(4) -0.0462(4) 0.3193(2) 0.0191(10) Uani 1 1 d . . . . .
C12 C 0.0292(4) -0.1432(4) 0.3017(2) 0.0184(10) Uani 1 1 d . . . . .
H12 H 0.0760 -0.1467 0.2705 0.022 Uiso 1 1 calc R U . . .
C13 C -0.0015(4) -0.2372(4) 0.3277(2) 0.0211(11) Uani 1 1 d . . . . .
C14 C 0.0495(5) -0.3347(4) 0.3120(2) 0.0265(12) Uani 1 1 d . . . . .
H14 H 0.0960 -0.3367 0.2806 0.032 Uiso 1 1 calc R U . . .
C15 C 0.0319(5) -0.4223(4) 0.3411(3) 0.0279(13) Uani 1 1 d . . . . .
H15 H 0.0732 -0.4839 0.3332 0.033 Uiso 1 1 calc R U . . .
C16 C -0.0485(5) -0.4248(4) 0.3841(3) 0.0266(13) Uani 1 1 d . . . . .
C17 C -0.0650(5) -0.5195(4) 0.4150(3) 0.0330(14) Uani 1 1 d . . . . .
H17 H -0.0194 -0.5789 0.4078 0.040 Uiso 1 1 calc R U . . .
C18 C -0.1428(6) -0.5267(4) 0.4537(3) 0.0381(16) Uani 1 1 d . . . . .
H18 H -0.1452 -0.5879 0.4766 0.046 Uiso 1 1 calc R U . . .
C19 C -0.2219(6) -0.4438(5) 0.4608(2) 0.0320(14) Uani 1 1 d . . . . .
C20 C -0.3136(6) -0.4532(5) 0.4960(3) 0.0384(16) Uani 1 1 d . . . . .
H20 H -0.3188 -0.5145 0.5185 0.046 Uiso 1 1 calc R U . . .
C21 C -0.3953(6) -0.3764(5) 0.4985(3) 0.0401(16) Uani 1 1 d . . . . .
H21 H -0.4541 -0.3830 0.5240 0.048 Uiso 1 1 calc R U . . .
C22 C -0.3912(5) -0.2883(5) 0.4633(2) 0.0322(14) Uani 1 1 d . . . . .
H22 H -0.4514 -0.2376 0.4625 0.039 Uiso 1 1 calc R U . . .
C23 C -0.3020(5) -0.2743(4) 0.4301(2) 0.0259(12) Uani 1 1 d . . . . .
H23 H -0.3010 -0.2133 0.4069 0.031 Uiso 1 1 calc R U . . .
C24 C -0.2109(5) -0.3479(4) 0.4292(2) 0.0264(12) Uani 1 1 d . . . . .
C25 C -0.1129(5) -0.3348(4) 0.3952(2) 0.0225(11) Uani 1 1 d . . . . .
C26 C -0.0786(4) -0.2371(4) 0.3716(2) 0.0178(10) Uani 1 1 d . . . . .
C27 C -0.1059(4) -0.1371(4) 0.3924(2) 0.0186(10) Uani 1 1 d . . . . .
H27 H -0.1501 -0.1328 0.4246 0.022 Uiso 1 1 calc R U . . .
C28 C -0.0710(4) -0.0458(4) 0.3680(2) 0.0183(10) Uani 1 1 d . . . . .
C29 C -0.1049(5) 0.0562(4) 0.3936(2) 0.0215(11) Uani 1 1 d . . . . .
H29A H -0.1722 0.0861 0.3686 0.026 Uiso 1 1 calc R U . . .
H29B H -0.1296 0.0435 0.4326 0.026 Uiso 1 1 calc R U . . .
C30 C 0.0550(4) 0.1515(4) 0.3543(2) 0.0195(11) Uani 1 1 d . . . . .
C31 C 0.0267(5) 0.1919(4) 0.4466(2) 0.0266(12) Uani 1 1 d . . . . .
H31 H -0.0054 0.1916 0.4826 0.032 Uiso 1 1 calc R U . . .
C32 C 0.1144(5) 0.2512(4) 0.4327(2) 0.0290(13) Uani 1 1 d . . . . .
H32 H 0.1569 0.3009 0.4571 0.035 Uiso 1 1 calc R U . . .
C33 C 0.2189(5) 0.2778(4) 0.3445(3) 0.0321(13) Uani 1 1 d . . . . .
H33A H 0.2628 0.3286 0.3699 0.048 Uiso 1 1 calc R U . . .
H33B H 0.2726 0.2254 0.3319 0.048 Uiso 1 1 calc R U . . .
H33C H 0.1794 0.3137 0.3103 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C41 1.738(8) . ?
Cl2 C41 1.725(7) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
Cl3 C42 1.697(9) . ?
Cl4 C42 1.725(9) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
Ir1 C30 1.998(5) . ?
Ir1 C11 2.048(5) . ?
Ir1 C4 2.149(5) . ?
Ir1 C5 2.216(5) . ?
Ir1 C3 2.228(5) . ?
Ir1 C1 2.250(5) . ?
Ir1 C2 2.261(5) . ?
Ir1 Br1 2.5533(6) . ?
N1 C30 1.352(6) . ?
N1 C31 1.380(6) . ?
N1 C29 1.460(6) . ?
N2 C30 1.369(6) . ?
N2 C32 1.384(7) . ?
N2 C33 1.458(7) . ?
C1 C5 1.428(8) . ?
C1 C2 1.469(7) . ?
C1 C6 1.469(8) . ?
C2 C3 1.400(7) . ?
C2 C7 1.485(7) . ?
C3 C4 1.454(8) . ?
C3 C8 1.509(8) . ?
C4 C5 1.451(9) . ?
C4 C9 1.491(7) . ?
C5 C10 1.479(8) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.382(7) . ?
C11 C28 1.427(7) . ?
C12 C13 1.410(7) . ?
C12 H12 0.9500 . ?
C13 C26 1.423(7) . ?
C13 C14 1.446(7) . ?
C14 C15 1.338(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.434(9) . ?
C15 H15 0.9500 . ?
C16 C25 1.411(7) . ?
C16 C17 1.434(7) . ?
C17 C18 1.340(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.422(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.411(9) . ?
C19 C24 1.444(8) . ?
C20 C21 1.368(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.364(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.413(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.458(8) . ?
C25 C26 1.440(7) . ?
C26 C27 1.418(7) . ?
C27 C28 1.380(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.505(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C31 C32 1.333(8) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
Cl2 C41 Cl1 112.9(4) . . ?
Cl2 C41 H41A 109.0 . . ?
Cl1 C41 H41A 109.0 . . ?
Cl2 C41 H41B 109.0 . . ?
Cl1 C41 H41B 109.0 . . ?
H41A C41 H41B 107.8 . . ?
Cl3 C42 Cl4 115.3(6) . . ?
Cl3 C42 H42A 108.5 . . ?
Cl4 C42 H42A 108.5 . . ?
Cl3 C42 H42B 108.5 . . ?
Cl4 C42 H42B 108.5 . . ?
H42A C42 H42B 107.5 . . ?
C30 Ir1 C11 84.82(19) . . ?
C30 Ir1 C4 106.4(2) . . ?
C11 Ir1 C4 105.4(2) . . ?
C30 Ir1 C5 142.8(2) . . ?
C11 Ir1 C5 92.7(2) . . ?
C4 Ir1 C5 38.8(2) . . ?
C30 Ir1 C3 97.56(19) . . ?
C11 Ir1 C3 143.4(2) . . ?
C4 Ir1 C3 38.8(2) . . ?
C5 Ir1 C3 63.6(2) . . ?
C30 Ir1 C1 158.68(19) . . ?
C11 Ir1 C1 115.6(2) . . ?
C4 Ir1 C1 63.8(2) . . ?
C5 Ir1 C1 37.3(2) . . ?
C3 Ir1 C1 62.60(18) . . ?
C30 Ir1 C2 121.06(19) . . ?
C11 Ir1 C2 153.27(19) . . ?
C4 Ir1 C2 63.3(2) . . ?
C5 Ir1 C2 62.97(19) . . ?
C3 Ir1 C2 36.33(18) . . ?
C1 Ir1 C2 38.00(18) . . ?
C30 Ir1 Br1 91.81(14) . . ?
C11 Ir1 Br1 88.29(14) . . ?
C4 Ir1 Br1 157.93(15) . . ?
C5 Ir1 Br1 125.26(16) . . ?
C3 Ir1 Br1 127.94(15) . . ?
C1 Ir1 Br1 94.83(14) . . ?
C2 Ir1 Br1 96.73(13) . . ?
C30 N1 C31 111.3(4) . . ?
C30 N1 C29 122.7(4) . . ?
C31 N1 C29 126.0(4) . . ?
C30 N2 C32 110.3(5) . . ?
C30 N2 C33 125.8(5) . . ?
C32 N2 C33 123.8(4) . . ?
C5 C1 C2 107.6(5) . . ?
C5 C1 C6 127.1(5) . . ?
C2 C1 C6 125.2(5) . . ?
C5 C1 Ir1 70.0(3) . . ?
C2 C1 Ir1 71.4(3) . . ?
C6 C1 Ir1 126.9(4) . . ?
C3 C2 C1 108.4(5) . . ?
C3 C2 C7 128.4(5) . . ?
C1 C2 C7 123.0(5) . . ?
C3 C2 Ir1 70.5(3) . . ?
C1 C2 Ir1 70.6(3) . . ?
C7 C2 Ir1 128.2(4) . . ?
C2 C3 C4 108.6(5) . . ?
C2 C3 C8 126.5(6) . . ?
C4 C3 C8 125.0(5) . . ?
C2 C3 Ir1 73.1(3) . . ?
C4 C3 Ir1 67.7(3) . . ?
C8 C3 Ir1 126.3(4) . . ?
C5 C4 C3 107.5(5) . . ?
C5 C4 C9 126.4(6) . . ?
C3 C4 C9 124.8(6) . . ?
C5 C4 Ir1 73.1(3) . . ?
C3 C4 Ir1 73.6(3) . . ?
C9 C4 Ir1 129.1(4) . . ?
C1 C5 C4 107.8(5) . . ?
C1 C5 C10 126.2(6) . . ?
C4 C5 C10 126.0(6) . . ?
C1 C5 Ir1 72.7(3) . . ?
C4 C5 Ir1 68.1(3) . . ?
C10 C5 Ir1 126.0(4) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C28 115.6(5) . . ?
C12 C11 Ir1 121.3(4) . . ?
C28 C11 Ir1 123.0(4) . . ?
C11 C12 C13 123.4(5) . . ?
C11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C12 C13 C26 120.7(5) . . ?
C12 C13 C14 120.3(5) . . ?
C26 C13 C14 119.0(5) . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 121.0(5) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C25 C16 C17 120.1(5) . . ?
C25 C16 C15 120.2(5) . . ?
C17 C16 C15 119.7(5) . . ?
C18 C17 C16 121.8(6) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 122.3(6) . . ?
C20 C19 C24 118.6(6) . . ?
C18 C19 C24 119.0(6) . . ?
C21 C20 C19 121.9(6) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 119.2(6) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 120.9(6) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 121.9(5) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C19 117.0(5) . . ?
C23 C24 C25 123.6(5) . . ?
C19 C24 C25 119.2(5) . . ?
C16 C25 C26 118.1(5) . . ?
C16 C25 C24 117.4(5) . . ?
C26 C25 C24 124.5(5) . . ?
C27 C26 C13 115.1(4) . . ?
C27 C26 C25 125.3(4) . . ?
C13 C26 C25 119.3(5) . . ?
C28 C27 C26 122.9(5) . . ?
C28 C27 H27 118.6 . . ?
C26 C27 H27 118.6 . . ?
C27 C28 C11 121.6(5) . . ?
C27 C28 C29 118.5(4) . . ?
C11 C28 C29 119.9(4) . . ?
N1 C29 C28 111.9(4) . . ?
N1 C29 H29A 109.2 . . ?
C28 C29 H29A 109.2 . . ?
N1 C29 H29B 109.2 . . ?
C28 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
N1 C30 N2 104.2(4) . . ?
N1 C30 Ir1 125.4(4) . . ?
N2 C30 Ir1 130.4(4) . . ?
C32 C31 N1 107.0(5) . . ?
C32 C31 H31 126.5 . . ?
N1 C31 H31 126.5 . . ?
C31 C32 N2 107.3(5) . . ?
C31 C32 H32 126.4 . . ?
N2 C32 H32 126.4 . . ?
N2 C33 H33A 109.5 . . ?
N2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
C5 C1 C2 C3 0.3(6) . . . . ?
C6 C1 C2 C3 176.8(5) . . . . ?
Ir1 C1 C2 C3 -60.7(3) . . . . ?
C5 C1 C2 C7 -175.4(5) . . . . ?
C6 C1 C2 C7 1.1(8) . . . . ?
Ir1 C1 C2 C7 123.6(5) . . . . ?
C5 C1 C2 Ir1 61.0(4) . . . . ?
C6 C1 C2 Ir1 -122.5(5) . . . . ?
C1 C2 C3 C4 2.1(6) . . . . ?
C7 C2 C3 C4 177.5(5) . . . . ?
Ir1 C2 C3 C4 -58.6(3) . . . . ?
C1 C2 C3 C8 -176.2(5) . . . . ?
C7 C2 C3 C8 -0.8(9) . . . . ?
Ir1 C2 C3 C8 123.1(5) . . . . ?
C1 C2 C3 Ir1 60.8(3) . . . . ?
C7 C2 C3 Ir1 -123.9(5) . . . . ?
C2 C3 C4 C5 -3.7(6) . . . . ?
C8 C3 C4 C5 174.6(5) . . . . ?
Ir1 C3 C4 C5 -65.7(4) . . . . ?
C2 C3 C4 C9 -171.4(5) . . . . ?
C8 C3 C4 C9 6.9(8) . . . . ?
Ir1 C3 C4 C9 126.5(5) . . . . ?
C2 C3 C4 Ir1 62.1(4) . . . . ?
C8 C3 C4 Ir1 -119.6(5) . . . . ?
C2 C1 C5 C4 -2.6(6) . . . . ?
C6 C1 C5 C4 -178.9(5) . . . . ?
Ir1 C1 C5 C4 59.3(3) . . . . ?
C2 C1 C5 C10 175.8(5) . . . . ?
C6 C1 C5 C10 -0.6(9) . . . . ?
Ir1 C1 C5 C10 -122.4(6) . . . . ?
C2 C1 C5 Ir1 -61.9(3) . . . . ?
C6 C1 C5 Ir1 121.7(5) . . . . ?
C3 C4 C5 C1 3.8(6) . . . . ?
C9 C4 C5 C1 171.3(5) . . . . ?
Ir1 C4 C5 C1 -62.2(4) . . . . ?
C3 C4 C5 C10 -174.5(5) . . . . ?
C9 C4 C5 C10 -7.0(9) . . . . ?
Ir1 C4 C5 C10 119.5(6) . . . . ?
C3 C4 C5 Ir1 66.0(3) . . . . ?
C9 C4 C5 Ir1 -126.5(6) . . . . ?
C28 C11 C12 C13 2.7(7) . . . . ?
Ir1 C11 C12 C13 -175.0(4) . . . . ?
C11 C12 C13 C26 4.8(7) . . . . ?
C11 C12 C13 C14 -172.3(5) . . . . ?
C12 C13 C14 C15 172.0(5) . . . . ?
C26 C13 C14 C15 -5.1(8) . . . . ?
C13 C14 C15 C16 7.3(8) . . . . ?
C14 C15 C16 C25 1.7(8) . . . . ?
C14 C15 C16 C17 -179.5(5) . . . . ?
C25 C16 C17 C18 1.7(8) . . . . ?
C15 C16 C17 C18 -177.0(6) . . . . ?
C16 C17 C18 C19 7.3(9) . . . . ?
C17 C18 C19 C20 172.5(6) . . . . ?
C17 C18 C19 C24 -5.1(8) . . . . ?
C18 C19 C20 C21 -174.2(6) . . . . ?
C24 C19 C20 C21 3.4(8) . . . . ?
C19 C20 C21 C22 3.1(9) . . . . ?
C20 C21 C22 C23 -5.2(9) . . . . ?
C21 C22 C23 C24 0.7(8) . . . . ?
C22 C23 C24 C19 5.7(8) . . . . ?
C22 C23 C24 C25 -178.9(5) . . . . ?
C20 C19 C24 C23 -7.7(7) . . . . ?
C18 C19 C24 C23 170.0(5) . . . . ?
C20 C19 C24 C25 176.7(5) . . . . ?
C18 C19 C24 C25 -5.6(7) . . . . ?
C17 C16 C25 C26 168.7(5) . . . . ?
C15 C16 C25 C26 -12.6(8) . . . . ?
C17 C16 C25 C24 -12.1(7) . . . . ?
C15 C16 C25 C24 166.6(5) . . . . ?
C23 C24 C25 C16 -161.4(5) . . . . ?
C19 C24 C25 C16 13.9(7) . . . . ?
C23 C24 C25 C26 17.8(8) . . . . ?
C19 C24 C25 C26 -166.9(5) . . . . ?
C12 C13 C26 C27 -9.2(7) . . . . ?
C14 C13 C26 C27 167.9(4) . . . . ?
C12 C13 C26 C25 176.9(4) . . . . ?
C14 C13 C26 C25 -6.0(7) . . . . ?
C16 C25 C26 C27 -158.7(5) . . . . ?
C24 C25 C26 C27 22.2(8) . . . . ?
C16 C25 C26 C13 14.5(7) . . . . ?
C24 C25 C26 C13 -164.6(5) . . . . ?
C13 C26 C27 C28 6.7(7) . . . . ?
C25 C26 C27 C28 -179.8(5) . . . . ?
C26 C27 C28 C11 0.6(7) . . . . ?
C26 C27 C28 C29 179.9(5) . . . . ?
C12 C11 C28 C27 -5.4(7) . . . . ?
Ir1 C11 C28 C27 172.2(4) . . . . ?
C12 C11 C28 C29 175.3(4) . . . . ?
Ir1 C11 C28 C29 -7.1(6) . . . . ?
C30 N1 C29 C28 48.6(6) . . . . ?
C31 N1 C29 C28 -134.1(5) . . . . ?
C27 C28 C29 N1 137.4(4) . . . . ?
C11 C28 C29 N1 -43.2(6) . . . . ?
C31 N1 C30 N2 0.5(6) . . . . ?
C29 N1 C30 N2 178.1(4) . . . . ?
C31 N1 C30 Ir1 -177.6(4) . . . . ?
C29 N1 C30 Ir1 0.1(7) . . . . ?
C32 N2 C30 N1 -0.2(6) . . . . ?
C33 N2 C30 N1 -178.4(5) . . . . ?
C32 N2 C30 Ir1 177.7(4) . . . . ?
C33 N2 C30 Ir1 -0.5(8) . . . . ?
C30 N1 C31 C32 -0.5(6) . . . . ?
C29 N1 C31 C32 -178.1(5) . . . . ?
N1 C31 C32 N2 0.4(6) . . . . ?
C30 N2 C32 C31 -0.1(6) . . . . ?
C33 N2 C32 C31 178.1(5) . . . . ?

_refine_diff_density_max         2.100
_refine_diff_density_min         -1.515
_refine_diff_density_rms         0.167

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/cc14fn8h
_database_code_depnum_ccdc_archive 'CCDC 1055806'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H36 Br Ir N2'
_chemical_formula_weight         828.83

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   13.7643(8)
_cell_length_b                   14.1122(7)
_cell_length_c                   16.9238(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3287.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    48393
_cell_measurement_theta_min      4.0490
_cell_measurement_theta_max      71.3920

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    9.522
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.44333
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_diffrn_ambient_temperature      150(2)
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0662
_diffrn_reflns_number            62658
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.079
_diffrn_reflns_theta_max         71.277
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6378
_reflns_number_gt                6369
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_cell_refinement       
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_data_reduction        
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.37.35'

_computing_structure_solution    'SIR-97_(Altomare & al., 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.3(CCDC, 2014)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+4.7495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6378
_refine_ls_number_parameters     413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0544
_refine_ls_wR_factor_gt          0.0544
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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_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 0.32855(2) 0.08760(2) 0.84818(2) 0.01290(7) Uani 1 1 d . . . . .
Br1 Br 0.49865(4) 0.13206(4) 0.80533(3) 0.02611(13) Uani 1 1 d . . . . .
N1 N 0.3821(3) -0.0900(3) 0.7533(3) 0.0234(9) Uani 1 1 d . . . . .
N2 N 0.2617(3) -0.0155(3) 0.7025(3) 0.0210(9) Uani 1 1 d . . . . .
C1 C 0.2110(4) 0.0644(4) 0.9298(3) 0.0210(11) Uani 1 1 d . . . . .
C2 C 0.2478(4) 0.1591(4) 0.9452(3) 0.0183(10) Uani 1 1 d . . . . .
C3 C 0.3466(4) 0.1508(4) 0.9681(3) 0.0187(10) Uani 1 1 d . . . . .
C4 C 0.3705(4) 0.0506(4) 0.9736(3) 0.0210(10) Uani 1 1 d . . . . .
C5 C 0.2865(4) -0.0024(4) 0.9520(3) 0.0214(11) Uani 1 1 d . . . . .
C6 C 0.1070(4) 0.0399(5) 0.9140(4) 0.0345(14) Uani 1 1 d . . . . .
H6A H 0.0711 0.0381 0.9640 0.052 Uiso 1 1 calc R U . . .
H6B H 0.1035 -0.0222 0.8883 0.052 Uiso 1 1 calc R U . . .
H6C H 0.0783 0.0879 0.8792 0.052 Uiso 1 1 calc R U . . .
C7 C 0.1900(4) 0.2479(4) 0.9379(3) 0.0272(12) Uani 1 1 d . . . . .
H7A H 0.1563 0.2605 0.9878 0.041 Uiso 1 1 calc R U . . .
H7B H 0.1421 0.2407 0.8954 0.041 Uiso 1 1 calc R U . . .
H7C H 0.2334 0.3008 0.9255 0.041 Uiso 1 1 calc R U . . .
C8 C 0.4149(4) 0.2298(4) 0.9879(3) 0.0261(12) Uani 1 1 d . . . . .
H8A H 0.3920 0.2885 0.9631 0.039 Uiso 1 1 calc R U . . .
H8B H 0.4799 0.2145 0.9681 0.039 Uiso 1 1 calc R U . . .
H8C H 0.4174 0.2381 1.0453 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4670(4) 0.0134(4) 1.0000(3) 0.0288(12) Uani 1 1 d . . . . .
H9A H 0.4653 -0.0560 1.0009 0.043 Uiso 1 1 calc R U . . .
H9B H 0.4814 0.0372 1.0532 0.043 Uiso 1 1 calc R U . . .
H9C H 0.5176 0.0347 0.9633 0.043 Uiso 1 1 calc R U . . .
C10 C 0.2746(5) -0.1074(4) 0.9546(4) 0.0334(14) Uani 1 1 d . . . . .
H10A H 0.3379 -0.1372 0.9638 0.050 Uiso 1 1 calc R U . . .
H10B H 0.2480 -0.1296 0.9041 0.050 Uiso 1 1 calc R U . . .
H10C H 0.2300 -0.1244 0.9974 0.050 Uiso 1 1 calc R U . . .
C11 C 0.4574(4) -0.1206(4) 0.8069(4) 0.0290(12) Uani 1 1 d . . . . .
H11A H 0.4795 -0.0665 0.8385 0.044 Uiso 1 1 calc R U . . .
H11B H 0.5122 -0.1461 0.7766 0.044 Uiso 1 1 calc R U . . .
H11C H 0.4318 -0.1698 0.8419 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3548(5) -0.1390(4) 0.6856(4) 0.0325(14) Uani 1 1 d . . . . .
H12 H 0.3841 -0.1949 0.6655 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2798(5) -0.0929(4) 0.6542(4) 0.0325(12) Uani 1 1 d . . . . .
H13 H 0.2453 -0.1097 0.6077 0.039 Uiso 1 1 calc R U . . .
C14 C 0.3243(4) -0.0124(3) 0.7632(3) 0.0183(9) Uani 1 1 d . . . . .
C15 C 0.1802(4) 0.0501(3) 0.6944(3) 0.0221(10) Uani 1 1 d . . . . .
H15A H 0.1310 0.0353 0.7352 0.027 Uiso 1 1 calc R U . . .
H15B H 0.1496 0.0408 0.6420 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2102(4) 0.1517(3) 0.7025(3) 0.0154(9) Uani 1 1 d . . . . .
C17 C 0.2754(3) 0.1791(3) 0.7634(3) 0.0141(9) Uani 1 1 d . . . . .
C18 C 0.3002(3) 0.2739(3) 0.7663(3) 0.0157(9) Uani 1 1 d . . . . .
H18 H 0.3450 0.2943 0.8055 0.019 Uiso 1 1 calc R U . . .
C19 C 0.2620(4) 0.3417(3) 0.7135(3) 0.0164(10) Uani 1 1 d . . . . .
C20 C 0.2970(4) 0.4376(3) 0.7147(3) 0.0214(11) Uani 1 1 d . . . . .
H20 H 0.3374 0.4584 0.7568 0.026 Uiso 1 1 calc R U . . .
C21 C 0.2727(4) 0.4982(3) 0.6560(4) 0.0233(10) Uani 1 1 d . . . . .
H21 H 0.3018 0.5592 0.6544 0.028 Uiso 1 1 calc R U . . .
C22 C 0.2043(4) 0.4724(4) 0.5965(3) 0.0205(10) Uani 1 1 d . . . . .
C23 C 0.1906(4) 0.5322(4) 0.5301(3) 0.0284(12) Uani 1 1 d . . . . .
H23 H 0.2214 0.5924 0.5286 0.034 Uiso 1 1 calc R U . . .
C24 C 0.1344(4) 0.5045(4) 0.4689(3) 0.0292(13) Uani 1 1 d . . . . .
H24 H 0.1338 0.5407 0.4215 0.035 Uiso 1 1 calc R U . . .
C25 C 0.0761(4) 0.4220(4) 0.4746(3) 0.0250(11) Uani 1 1 d . . . . .
C26 C 0.0159(5) 0.3946(4) 0.4104(3) 0.0330(14) Uani 1 1 d . . . . .
H26 H 0.0161 0.4310 0.3632 0.040 Uiso 1 1 calc R U . . .
C27 C -0.0421(4) 0.3168(4) 0.4157(3) 0.0298(13) Uani 1 1 d . . . . .
H27 H -0.0743 0.2935 0.3700 0.036 Uiso 1 1 calc R U . . .
C28 C -0.0546(4) 0.2705(4) 0.4894(3) 0.0248(11) Uani 1 1 d . . . . .
C29 C -0.1230(4) 0.1938(4) 0.4959(4) 0.0315(13) Uani 1 1 d . . . . .
H29 H -0.1527 0.1694 0.4495 0.038 Uiso 1 1 calc R U . . .
C30 C -0.1455(4) 0.1565(4) 0.5660(4) 0.0338(14) Uani 1 1 d . . . . .
H30 H -0.1878 0.1034 0.5684 0.041 Uiso 1 1 calc R U . . .
C31 C -0.1071(4) 0.1947(4) 0.6373(4) 0.0292(12) Uani 1 1 d . . . . .
C32 C -0.1398(5) 0.1632(5) 0.7112(5) 0.0448(18) Uani 1 1 d . . . . .
H32 H -0.1824 0.1104 0.7138 0.054 Uiso 1 1 calc R U . . .
C33 C -0.1117(6) 0.2070(6) 0.7801(5) 0.052(2) Uani 1 1 d . . . . .
H33 H -0.1331 0.1835 0.8298 0.062 Uiso 1 1 calc R U . . .
C34 C -0.0509(5) 0.2870(5) 0.7764(4) 0.0351(14) Uani 1 1 d . . . . .
H34 H -0.0339 0.3198 0.8234 0.042 Uiso 1 1 calc R U . . .
C35 C -0.0164(4) 0.3175(4) 0.7053(3) 0.0237(11) Uani 1 1 d . . . . .
H35 H 0.0245 0.3717 0.7039 0.028 Uiso 1 1 calc R U . . .
C36 C -0.0395(4) 0.2707(4) 0.6334(3) 0.0216(11) Uani 1 1 d . . . . .
C37 C -0.0029(4) 0.3013(3) 0.5571(3) 0.0191(10) Uani 1 1 d . . . . .
C38 C 0.0758(4) 0.3674(4) 0.5457(3) 0.0183(10) Uani 1 1 d . . . . .
C39 C 0.1549(3) 0.3846(3) 0.6011(3) 0.0172(9) Uani 1 1 d . . . . .
C40 C 0.1928(3) 0.3144(3) 0.6559(3) 0.0154(9) Uani 1 1 d . . . . .
C41 C 0.1715(3) 0.2167(3) 0.6517(3) 0.0166(8) Uani 1 1 d . . . . .
H41 H 0.1283 0.1952 0.6117 0.020 Uiso 1 1 calc R U . . .


_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 C14 2.016(5) . ?
Ir1 C17 2.064(5) . ?
Ir1 C1 2.152(5) . ?
Ir1 C2 2.225(5) . ?
Ir1 C3 2.230(5) . ?
Ir1 C5 2.245(5) . ?
Ir1 C4 2.261(5) . ?
Ir1 Br1 2.5301(6) . ?
N1 C14 1.364(7) . ?
N1 C12 1.390(7) . ?
N1 C11 1.443(7) . ?
N2 C14 1.341(7) . ?
N2 C13 1.386(7) . ?
N2 C15 1.461(6) . ?
C1 C5 1.452(8) . ?
C1 C2 1.453(7) . ?
C1 C6 1.497(7) . ?
C2 C3 1.419(7) . ?
C2 C7 1.489(7) . ?
C3 C4 1.455(7) . ?
C3 C8 1.496(7) . ?
C4 C5 1.425(8) . ?
C4 C9 1.497(8) . ?
C5 C10 1.491(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.330(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 C16 1.499(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C41 1.365(7) . ?
C16 C17 1.421(7) . ?
C17 C18 1.382(7) . ?
C18 C19 1.410(7) . ?
C18 H18 0.9500 . ?
C19 C40 1.417(7) . ?
C19 C20 1.436(7) . ?
C20 C21 1.353(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.426(8) . ?
C21 H21 0.9500 . ?
C22 C39 1.416(7) . ?
C22 C23 1.418(7) . ?
C23 C24 1.351(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.417(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.422(8) . ?
C25 C38 1.429(7) . ?
C26 C27 1.360(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.419(8) . ?
C27 H27 0.9500 . ?
C28 C37 1.418(7) . ?
C28 C29 1.438(9) . ?
C29 C30 1.335(10) . ?
C29 H29 0.9500 . ?
C30 C31 1.422(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.402(10) . ?
C31 C36 1.422(8) . ?
C32 C33 1.375(11) . ?
C32 H32 0.9500 . ?
C33 C34 1.406(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.362(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.420(7) . ?
C35 H35 0.9500 . ?
C36 C37 1.452(7) . ?
C37 C38 1.441(8) . ?
C38 C39 1.457(7) . ?
C39 C40 1.454(6) . ?
C40 C41 1.411(6) . ?
C41 H41 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 Ir1 C17 86.08(19) . . ?
C14 Ir1 C1 109.2(2) . . ?
C17 Ir1 C1 106.0(2) . . ?
C14 Ir1 C2 146.0(2) . . ?
C17 Ir1 C2 93.01(18) . . ?
C1 Ir1 C2 38.72(19) . . ?
C14 Ir1 C3 158.79(18) . . ?
C17 Ir1 C3 114.95(18) . . ?
C1 Ir1 C3 63.93(19) . . ?
C2 Ir1 C3 37.14(19) . . ?
C14 Ir1 C5 98.90(19) . . ?
C17 Ir1 C5 143.8(2) . . ?
C1 Ir1 C5 38.5(2) . . ?
C2 Ir1 C5 63.25(19) . . ?
C3 Ir1 C5 62.80(19) . . ?
C14 Ir1 C4 121.03(19) . . ?
C17 Ir1 C4 152.6(2) . . ?
C1 Ir1 C4 63.5(2) . . ?
C2 Ir1 C4 62.57(19) . . ?
C3 Ir1 C4 37.79(19) . . ?
C5 Ir1 C4 36.9(2) . . ?
C14 Ir1 Br1 89.78(16) . . ?
C17 Ir1 Br1 88.49(13) . . ?
C1 Ir1 Br1 156.51(15) . . ?
C2 Ir1 Br1 124.16(14) . . ?
C3 Ir1 Br1 93.35(13) . . ?
C5 Ir1 Br1 127.11(14) . . ?
C4 Ir1 Br1 95.15(14) . . ?
C14 N1 C12 110.0(4) . . ?
C14 N1 C11 125.6(4) . . ?
C12 N1 C11 124.3(5) . . ?
C14 N2 C13 111.2(4) . . ?
C14 N2 C15 123.0(4) . . ?
C13 N2 C15 125.6(4) . . ?
C5 C1 C2 107.6(5) . . ?
C5 C1 C6 125.5(5) . . ?
C2 C1 C6 125.2(5) . . ?
C5 C1 Ir1 74.2(3) . . ?
C2 C1 Ir1 73.4(3) . . ?
C6 C1 Ir1 129.7(4) . . ?
C3 C2 C1 107.9(5) . . ?
C3 C2 C7 127.2(5) . . ?
C1 C2 C7 125.0(5) . . ?
C3 C2 Ir1 71.6(3) . . ?
C1 C2 Ir1 67.9(3) . . ?
C7 C2 Ir1 125.9(4) . . ?
C2 C3 C4 108.3(5) . . ?
C2 C3 C8 127.0(5) . . ?
C4 C3 C8 124.6(5) . . ?
C2 C3 Ir1 71.2(3) . . ?
C4 C3 Ir1 72.2(3) . . ?
C8 C3 Ir1 124.9(3) . . ?
C5 C4 C3 108.1(5) . . ?
C5 C4 C9 127.8(5) . . ?
C3 C4 C9 124.1(5) . . ?
C5 C4 Ir1 70.9(3) . . ?
C3 C4 Ir1 70.0(3) . . ?
C9 C4 Ir1 126.0(4) . . ?
C4 C5 C1 107.8(4) . . ?
C4 C5 C10 127.2(5) . . ?
C1 C5 C10 125.0(5) . . ?
C4 C5 Ir1 72.2(3) . . ?
C1 C5 Ir1 67.3(3) . . ?
C10 C5 Ir1 127.8(4) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 107.2(5) . . ?
C13 C12 H12 126.4 . . ?
N1 C12 H12 126.4 . . ?
C12 C13 N2 106.8(5) . . ?
C12 C13 H13 126.6 . . ?
N2 C13 H13 126.6 . . ?
N2 C14 N1 104.7(4) . . ?
N2 C14 Ir1 126.0(4) . . ?
N1 C14 Ir1 129.2(4) . . ?
N2 C15 C16 112.7(4) . . ?
N2 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C41 C16 C17 121.4(4) . . ?
C41 C16 C15 118.6(4) . . ?
C17 C16 C15 120.0(4) . . ?
C18 C17 C16 116.4(4) . . ?
C18 C17 Ir1 119.6(3) . . ?
C16 C17 Ir1 124.0(3) . . ?
C17 C18 C19 122.9(4) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C18 C19 C40 120.1(4) . . ?
C18 C19 C20 120.3(4) . . ?
C40 C19 C20 119.4(4) . . ?
C21 C20 C19 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.4(5) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C39 C22 C23 120.0(5) . . ?
C39 C22 C21 120.1(5) . . ?
C23 C22 C21 119.7(5) . . ?
C24 C23 C22 120.8(5) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.6(5) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 120.1(5) . . ?
C24 C25 C38 120.2(5) . . ?
C26 C25 C38 119.7(5) . . ?
C27 C26 C25 120.7(5) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 120.1(5) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C37 C28 C27 120.5(5) . . ?
C37 C28 C29 119.9(5) . . ?
C27 C28 C29 119.6(5) . . ?
C30 C29 C28 121.1(6) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C29 C30 C31 121.2(6) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C32 C31 C30 121.2(6) . . ?
C32 C31 C36 119.3(6) . . ?
C30 C31 C36 119.3(6) . . ?
C33 C32 C31 121.7(6) . . ?
C33 C32 H32 119.2 . . ?
C31 C32 H32 119.2 . . ?
C32 C33 C34 119.3(6) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C35 C34 C33 120.1(6) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 122.1(5) . . ?
C34 C35 H35 119.0 . . ?
C36 C35 H35 119.0 . . ?
C35 C36 C31 117.2(5) . . ?
C35 C36 C37 123.1(5) . . ?
C31 C36 C37 119.5(5) . . ?
C28 C37 C38 117.9(5) . . ?
C28 C37 C36 116.9(5) . . ?
C38 C37 C36 124.9(4) . . ?
C25 C38 C37 117.7(5) . . ?
C25 C38 C39 116.7(5) . . ?
C37 C38 C39 125.7(4) . . ?
C22 C39 C40 117.3(4) . . ?
C22 C39 C38 118.0(4) . . ?
C40 C39 C38 124.4(4) . . ?
C41 C40 C19 116.1(4) . . ?
C41 C40 C39 124.0(4) . . ?
C19 C40 C39 119.7(4) . . ?
C16 C41 C40 122.9(4) . . ?
C16 C41 H41 118.5 . . ?
C40 C41 H41 118.5 . . ?

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
C5 C1 C2 C3 6.1(5) . . . . ?
C6 C1 C2 C3 172.0(5) . . . . ?
Ir1 C1 C2 C3 -60.8(3) . . . . ?
C5 C1 C2 C7 -173.9(5) . . . . ?
C6 C1 C2 C7 -8.0(8) . . . . ?
Ir1 C1 C2 C7 119.3(5) . . . . ?
C5 C1 C2 Ir1 66.9(3) . . . . ?
C6 C1 C2 Ir1 -127.2(6) . . . . ?
C1 C2 C3 C4 -4.7(5) . . . . ?
C7 C2 C3 C4 175.3(5) . . . . ?
Ir1 C2 C3 C4 -63.1(3) . . . . ?
C1 C2 C3 C8 178.4(5) . . . . ?
C7 C2 C3 C8 -1.6(8) . . . . ?
Ir1 C2 C3 C8 120.0(5) . . . . ?
C1 C2 C3 Ir1 58.5(3) . . . . ?
C7 C2 C3 Ir1 -121.6(5) . . . . ?
C2 C3 C4 C5 1.5(6) . . . . ?
C8 C3 C4 C5 178.5(5) . . . . ?
Ir1 C3 C4 C5 -61.0(3) . . . . ?
C2 C3 C4 C9 -176.9(5) . . . . ?
C8 C3 C4 C9 0.1(8) . . . . ?
Ir1 C3 C4 C9 120.6(5) . . . . ?
C2 C3 C4 Ir1 62.5(3) . . . . ?
C8 C3 C4 Ir1 -120.5(5) . . . . ?
C3 C4 C5 C1 2.3(6) . . . . ?
C9 C4 C5 C1 -179.4(5) . . . . ?
Ir1 C4 C5 C1 -58.1(3) . . . . ?
C3 C4 C5 C10 -175.2(5) . . . . ?
C9 C4 C5 C10 3.0(9) . . . . ?
Ir1 C4 C5 C10 124.4(6) . . . . ?
C3 C4 C5 Ir1 60.4(3) . . . . ?
C9 C4 C5 Ir1 -121.3(5) . . . . ?
C2 C1 C5 C4 -5.1(5) . . . . ?
C6 C1 C5 C4 -171.0(5) . . . . ?
Ir1 C1 C5 C4 61.1(3) . . . . ?
C2 C1 C5 C10 172.5(5) . . . . ?
C6 C1 C5 C10 6.6(9) . . . . ?
Ir1 C1 C5 C10 -121.3(5) . . . . ?
C2 C1 C5 Ir1 -66.3(3) . . . . ?
C6 C1 C5 Ir1 127.8(6) . . . . ?
C14 N1 C12 C13 -0.7(7) . . . . ?
C11 N1 C12 C13 176.2(6) . . . . ?
N1 C12 C13 N2 0.3(7) . . . . ?
C14 N2 C13 C12 0.2(7) . . . . ?
C15 N2 C13 C12 -174.2(5) . . . . ?
C13 N2 C14 N1 -0.7(6) . . . . ?
C15 N2 C14 N1 173.9(5) . . . . ?
C13 N2 C14 Ir1 179.0(4) . . . . ?
C15 N2 C14 Ir1 -6.4(7) . . . . ?
C12 N1 C14 N2 0.9(6) . . . . ?
C11 N1 C14 N2 -176.1(5) . . . . ?
C12 N1 C14 Ir1 -178.8(4) . . . . ?
C11 N1 C14 Ir1 4.3(8) . . . . ?
C14 N2 C15 C16 50.9(7) . . . . ?
C13 N2 C15 C16 -135.3(6) . . . . ?
N2 C15 C16 C41 137.8(5) . . . . ?
N2 C15 C16 C17 -44.0(7) . . . . ?
C41 C16 C17 C18 -2.5(7) . . . . ?
C15 C16 C17 C18 179.3(5) . . . . ?
C41 C16 C17 Ir1 174.9(4) . . . . ?
C15 C16 C17 Ir1 -3.3(7) . . . . ?
C16 C17 C18 C19 1.6(7) . . . . ?
Ir1 C17 C18 C19 -175.9(4) . . . . ?
C17 C18 C19 C40 2.0(7) . . . . ?
C17 C18 C19 C20 -174.4(5) . . . . ?
C18 C19 C20 C21 168.9(5) . . . . ?
C40 C19 C20 C21 -7.5(8) . . . . ?
C19 C20 C21 C22 6.7(8) . . . . ?
C20 C21 C22 C39 4.6(8) . . . . ?
C20 C21 C22 C23 -171.2(5) . . . . ?
C39 C22 C23 C24 -3.1(8) . . . . ?
C21 C22 C23 C24 172.7(5) . . . . ?
C22 C23 C24 C25 9.6(9) . . . . ?
C23 C24 C25 C26 178.8(5) . . . . ?
C23 C24 C25 C38 0.4(8) . . . . ?
C24 C25 C26 C27 -178.5(5) . . . . ?
C38 C25 C26 C27 -0.1(8) . . . . ?
C25 C26 C27 C28 9.8(8) . . . . ?
C26 C27 C28 C37 -3.6(8) . . . . ?
C26 C27 C28 C29 174.2(5) . . . . ?
C37 C28 C29 C30 6.2(8) . . . . ?
C27 C28 C29 C30 -171.6(6) . . . . ?
C28 C29 C30 C31 3.8(9) . . . . ?
C29 C30 C31 C32 172.0(7) . . . . ?
C29 C30 C31 C36 -3.5(9) . . . . ?
C30 C31 C32 C33 -172.4(8) . . . . ?
C36 C31 C32 C33 3.1(11) . . . . ?
C31 C32 C33 C34 1.9(13) . . . . ?
C32 C33 C34 C35 -3.4(12) . . . . ?
C33 C34 C35 C36 -0.1(10) . . . . ?
C34 C35 C36 C31 5.0(8) . . . . ?
C34 C35 C36 C37 -179.4(6) . . . . ?
C32 C31 C36 C35 -6.4(8) . . . . ?
C30 C31 C36 C35 169.2(5) . . . . ?
C32 C31 C36 C37 177.8(6) . . . . ?
C30 C31 C36 C37 -6.6(8) . . . . ?
C27 C28 C37 C38 -12.1(7) . . . . ?
C29 C28 C37 C38 170.2(5) . . . . ?
C27 C28 C37 C36 162.1(5) . . . . ?
C29 C28 C37 C36 -15.6(7) . . . . ?
C35 C36 C37 C28 -159.7(5) . . . . ?
C31 C36 C37 C28 15.8(7) . . . . ?
C35 C36 C37 C38 14.1(8) . . . . ?
C31 C36 C37 C38 -170.4(5) . . . . ?
C24 C25 C38 C37 163.0(5) . . . . ?
C26 C25 C38 C37 -15.4(7) . . . . ?
C24 C25 C38 C39 -16.2(7) . . . . ?
C26 C25 C38 C39 165.4(5) . . . . ?
C28 C37 C38 C25 21.1(7) . . . . ?
C36 C37 C38 C25 -152.6(5) . . . . ?
C28 C37 C38 C39 -159.8(5) . . . . ?
C36 C37 C38 C39 26.5(8) . . . . ?
C23 C22 C39 C40 161.3(5) . . . . ?
C21 C22 C39 C40 -14.4(7) . . . . ?
C23 C22 C39 C38 -13.0(7) . . . . ?
C21 C22 C39 C38 171.2(5) . . . . ?
C25 C38 C39 C22 22.2(7) . . . . ?
C37 C38 C39 C22 -157.0(5) . . . . ?
C25 C38 C39 C40 -151.8(5) . . . . ?
C37 C38 C39 C40 29.1(8) . . . . ?
C18 C19 C40 C41 -4.4(7) . . . . ?
C20 C19 C40 C41 172.0(4) . . . . ?
C18 C19 C40 C39 -179.2(4) . . . . ?
C20 C19 C40 C39 -2.8(7) . . . . ?
C22 C39 C40 C41 -160.8(5) . . . . ?
C38 C39 C40 C41 13.1(8) . . . . ?
C22 C39 C40 C19 13.5(7) . . . . ?
C38 C39 C40 C19 -172.6(4) . . . . ?
C17 C16 C41 C40 -0.1(8) . . . . ?
C15 C16 C41 C40 178.1(5) . . . . ?
C19 C40 C41 C16 3.6(7) . . . . ?
C39 C40 C41 C16 178.1(5) . . . . ?

_refine_diff_density_max         0.831
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.090

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_NH323
_database_code_depnum_ccdc_archive 'CCDC 1480527'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                              CHEMICAL_INFORMATION                          #
#----------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C33 H32 Br Ir N2'
_chemical_formula_sum            'C33 H32 Br Ir N2'
_chemical_formula_weight         728.71
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                             UNIT CELL INFORMATION                          #
#----------------------------------------------------------------------------#


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.2873(8)
_cell_length_b                   16.9087(16)
_cell_length_c                   17.4950(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2747.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.44
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                              CRYSTAL INFORMATION                           #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1424
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                             ABSORPTION CORRECTION                          #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.417
_exptl_absorpt_correction_T_max  0.728

#----------------------------------------------------------------------------#
#                                DATA COLLECTION                             #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0623
_diffrn_reflns_av_uneti/neti     0.0615
_diffrn_reflns_number            22563
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.199
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             6266
_reflns_number_gt                5315
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                             COMPUTER PROGRAMS USED                         #
#----------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'

#----------------------------------------------------------------------------#
#                             REFINEMENT INFORMATION                         #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+18.8014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6266
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.968
_refine_diff_density_min         -2.452
_refine_diff_density_rms         0.203
_refine_ls_abs_structure_details 
;
Flack x determined using 2090 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.039(8)

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS            #
#----------------------------------------------------------------------------#

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.42397(5) 0.15616(3) 0.33690(3) 0.02499(14) Uani 1 1 d . . . . .
Br1 Br 0.15396(15) 0.13214(10) 0.33429(11) 0.0413(4) Uani 1 1 d . . . . .
C1 C 0.4552(8) 0.1099(6) 0.2167(5) 0.0310(14) Uani 1 1 d G . . . .
C2 C 0.4912(10) 0.0492(5) 0.2695(6) 0.0310(14) Uani 1 1 d G . . . .
C3 C 0.6052(9) 0.0773(6) 0.3163(5) 0.0310(14) Uani 1 1 d G . . . .
C4 C 0.6397(8) 0.1553(5) 0.2925(5) 0.0310(14) Uani 1 1 d G . . . .
C5 C 0.5470(10) 0.1754(5) 0.2309(5) 0.0310(14) Uani 1 1 d G . . . .
C6 C 0.3393(16) 0.1043(12) 0.1585(10) 0.050(4) Uani 1 1 d . . . . .
H6A H 0.2864 0.1544 0.1565 0.075 Uiso 1 1 calc R U . . .
H6B H 0.2732 0.0614 0.1722 0.075 Uiso 1 1 calc R U . . .
H6C H 0.3820 0.0934 0.1084 0.075 Uiso 1 1 calc R U . . .
C7 C 0.423(2) -0.0319(10) 0.2698(10) 0.050(4) Uani 1 1 d . . . . .
H7A H 0.4573 -0.0621 0.2257 0.075 Uiso 1 1 calc R U . . .
H7B H 0.3178 -0.0265 0.2670 0.075 Uiso 1 1 calc R U . . .
H7C H 0.4488 -0.0596 0.3170 0.075 Uiso 1 1 calc R U . . .
C8 C 0.686(2) 0.0314(14) 0.3770(10) 0.064(6) Uani 1 1 d . . . . .
H8A H 0.6319 -0.0166 0.3899 0.096 Uiso 1 1 calc R U . . .
H8B H 0.6963 0.0643 0.4229 0.096 Uiso 1 1 calc R U . . .
H8C H 0.7812 0.0169 0.3577 0.096 Uiso 1 1 calc R U . . .
C9 C 0.773(2) 0.2043(13) 0.3181(14) 0.069(7) Uani 1 1 d . . . . .
H9A H 0.8529 0.1951 0.2824 0.103 Uiso 1 1 calc R U . . .
H9B H 0.8023 0.1879 0.3696 0.103 Uiso 1 1 calc R U . . .
H9C H 0.7487 0.2607 0.3184 0.103 Uiso 1 1 calc R U . . .
C11 C 0.330(2) 0.0075(10) 0.4670(9) 0.046(4) Uani 1 1 d . . . . .
H11A H 0.2769 0.0171 0.4193 0.069 Uiso 1 1 calc R U . . .
H11B H 0.2635 -0.0142 0.5053 0.069 Uiso 1 1 calc R U . . .
H11C H 0.4075 -0.0303 0.4576 0.069 Uiso 1 1 calc R U . . .
C10 C 0.5584(17) 0.2490(10) 0.1844(11) 0.047(5) Uani 1 1 d . . . . .
H10A H 0.6235 0.2863 0.2098 0.071 Uiso 1 1 calc R U . . .
H10B H 0.4629 0.2731 0.1791 0.071 Uiso 1 1 calc R U . . .
H10C H 0.5963 0.2360 0.1336 0.071 Uiso 1 1 calc R U . . .
N12 N 0.3896(13) 0.0815(8) 0.4947(7) 0.035(3) Uani 1 1 d . . . . .
C13 C 0.418(2) 0.0961(11) 0.5715(8) 0.042(4) Uani 1 1 d . . . . .
H13 H 0.4012 0.0613 0.6132 0.051 Uiso 1 1 calc R U . . .
C14 C 0.4744(17) 0.1679(11) 0.5752(8) 0.041(4) Uani 1 1 d . . . . .
H14 H 0.5046 0.1944 0.6203 0.049 Uiso 1 1 calc R U . . .
N15 N 0.4813(13) 0.1975(7) 0.5011(7) 0.032(3) Uani 1 1 d . . . . .
C16 C 0.4264(15) 0.1435(9) 0.4511(6) 0.029(3) Uani 1 1 d . . . . .
C17 C 0.5387(17) 0.2742(9) 0.4777(10) 0.039(4) Uani 1 1 d . . . . .
H17A H 0.6333 0.2667 0.4527 0.047 Uiso 1 1 calc R U . . .
H17B H 0.5531 0.3079 0.5234 0.047 Uiso 1 1 calc R U . . .
C21 C 0.3851(14) 0.2740(9) 0.3591(8) 0.030(3) Uani 1 1 d . . . . .
C22 C 0.2971(14) 0.3189(8) 0.3107(8) 0.026(3) Uani 1 1 d . . . . .
H22 H 0.2612 0.2951 0.2654 0.031 Uiso 1 1 calc R U . . .
C23 C 0.2595(14) 0.3985(8) 0.3267(8) 0.029(3) Uani 1 1 d . . . . .
C24 C 0.1606(16) 0.4378(10) 0.2772(8) 0.035(3) Uani 1 1 d . . . . .
H24 H 0.1300 0.4123 0.2316 0.042 Uiso 1 1 calc R U . . .
C25 C 0.1095(16) 0.5106(9) 0.2940(9) 0.035(3) Uani 1 1 d . . . . .
H25 H 0.0408 0.5350 0.2615 0.042 Uiso 1 1 calc R U . . .
C26 C 0.159(2) 0.5505(10) 0.3608(10) 0.0451(13) Uani 1 1 d . . . . .
C27 C 0.086(2) 0.6244(9) 0.3801(10) 0.0451(13) Uani 1 1 d . . . . .
H27 H 0.0125 0.6448 0.3479 0.054 Uiso 1 1 calc R U . . .
C28 C 0.1250(18) 0.6630(10) 0.4446(9) 0.0451(13) Uani 1 1 d . . . . .
H28 H 0.0686 0.7071 0.4598 0.054 Uiso 1 1 calc R U . . .
C29 C 0.2487(19) 0.6414(9) 0.4928(10) 0.0451(13) Uani 1 1 d . . . . .
C30 C 0.294(2) 0.6866(10) 0.5528(10) 0.0451(13) Uani 1 1 d . . . . .
H30 H 0.2401 0.7322 0.5666 0.054 Uiso 1 1 calc R U . . .
C31 C 0.4095(19) 0.6687(9) 0.5916(10) 0.0451(13) Uani 1 1 d . . . . .
H31 H 0.4355 0.6999 0.6346 0.054 Uiso 1 1 calc R U . . .
C32 C 0.498(2) 0.6026(9) 0.5702(10) 0.0451(13) Uani 1 1 d . . . . .
H32 H 0.5843 0.5911 0.5967 0.054 Uiso 1 1 calc R U . . .
C33 C 0.4519(18) 0.5561(9) 0.5096(10) 0.0451(13) Uani 1 1 d . . . . .
H33 H 0.5102 0.5128 0.4940 0.054 Uiso 1 1 calc R U . . .
C34 C 0.324(2) 0.5705(10) 0.4709(10) 0.0451(13) Uani 1 1 d . . . . .
C35 C 0.268(2) 0.5191(9) 0.4075(10) 0.0451(13) Uani 1 1 d . . . . .
C36 C 0.3137(13) 0.4391(8) 0.3928(8) 0.026(3) Uani 1 1 d . . . . .
C37 C 0.4005(15) 0.3919(8) 0.4404(8) 0.029(3) Uani 1 1 d . . . . .
H37 H 0.4355 0.4143 0.4866 0.035 Uiso 1 1 calc R U . . .
C38 C 0.4377(15) 0.3148(8) 0.4233(8) 0.027(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                               MOLECULAR GEOMETRY                           #
#----------------------------------------------------------------------------#

_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 2.009(11) . ?
Ir1 C21 2.061(14) . ?
Ir1 C4 2.149(9) . ?
Ir1 C3 2.177(9) . ?
Ir1 C5 2.202(9) . ?
Ir1 C2 2.247(9) . ?
Ir1 C1 2.262(9) . ?
Ir1 Br1 2.5407(14) . ?
C1 C5 1.4200 . ?
C1 C2 1.4200 . ?
C1 C6 1.485(17) . ?
C2 C3 1.4200 . ?
C2 C7 1.512(18) . ?
C3 C4 1.4200 . ?
C3 C8 1.513(19) . ?
C4 C5 1.4200 . ?
C4 C9 1.558(19) . ?
C5 C10 1.490(17) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 N12 1.45(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N12 C16 1.342(19) . ?
N12 C13 1.392(19) . ?
C13 C14 1.32(3) . ?
C13 H13 0.9500 . ?
C14 N15 1.39(2) . ?
C14 H14 0.9500 . ?
N15 C16 1.363(17) . ?
N15 C17 1.46(2) . ?
C17 C38 1.501(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C21 C22 1.401(19) . ?
C21 C38 1.406(18) . ?
C22 C23 1.418(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.425(19) . ?
C23 C36 1.44(2) . ?
C24 C25 1.35(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.43(2) . ?
C25 H25 0.9500 . ?
C26 C35 1.40(3) . ?
C26 C27 1.46(2) . ?
C27 C28 1.35(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.47(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.36(2) . ?
C29 C34 1.44(2) . ?
C30 C31 1.31(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.44(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.39(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.39(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.50(3) . ?
C35 C36 1.44(2) . ?
C36 C37 1.407(19) . ?
C37 C38 1.382(19) . ?
C37 H37 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 Ir1 C21 85.2(6) . . ?
C16 Ir1 C4 110.4(4) . . ?
C21 Ir1 C4 103.8(5) . . ?
C16 Ir1 C3 95.2(4) . . ?
C21 Ir1 C3 139.3(5) . . ?
C4 Ir1 C3 38.32(14) . . ?
C16 Ir1 C5 147.9(5) . . ?
C21 Ir1 C5 96.1(4) . . ?
C4 Ir1 C5 38.07(14) . . ?
C3 Ir1 C5 63.28(17) . . ?
C16 Ir1 C2 115.7(5) . . ?
C21 Ir1 C2 157.7(5) . . ?
C4 Ir1 C2 62.98(17) . . ?
C3 Ir1 C2 37.40(14) . . ?
C5 Ir1 C2 62.17(18) . . ?
C16 Ir1 C1 152.4(5) . . ?
C21 Ir1 C1 122.1(5) . . ?
C4 Ir1 C1 62.72(18) . . ?
C3 Ir1 C1 62.31(18) . . ?
C5 Ir1 C1 37.06(14) . . ?
C2 Ir1 C1 36.71(14) . . ?
C16 Ir1 Br1 90.7(4) . . ?
C21 Ir1 Br1 89.1(4) . . ?
C4 Ir1 Br1 155.9(2) . . ?
C3 Ir1 Br1 131.5(3) . . ?
C5 Ir1 Br1 121.4(2) . . ?
C2 Ir1 Br1 97.8(2) . . ?
C1 Ir1 Br1 93.1(2) . . ?
C5 C1 C2 108.0 . . ?
C5 C1 C6 127.2(10) . . ?
C2 C1 C6 124.8(10) . . ?
C5 C1 Ir1 69.2(3) . . ?
C2 C1 Ir1 71.1(3) . . ?
C6 C1 Ir1 124.5(8) . . ?
C3 C2 C1 108.0 . . ?
C3 C2 C7 127.9(10) . . ?
C1 C2 C7 124.0(10) . . ?
C3 C2 Ir1 68.6(3) . . ?
C1 C2 Ir1 72.2(3) . . ?
C7 C2 Ir1 127.7(9) . . ?
C2 C3 C4 108.0 . . ?
C2 C3 C8 127.0(12) . . ?
C4 C3 C8 124.8(12) . . ?
C2 C3 Ir1 74.0(4) . . ?
C4 C3 Ir1 69.8(4) . . ?
C8 C3 Ir1 125.4(9) . . ?
C5 C4 C3 108.0 . . ?
C5 C4 C9 125.0(12) . . ?
C3 C4 C9 126.1(12) . . ?
C5 C4 Ir1 73.0(4) . . ?
C3 C4 Ir1 71.9(4) . . ?
C9 C4 Ir1 129.4(9) . . ?
C4 C5 C1 108.0 . . ?
C4 C5 C10 124.8(10) . . ?
C1 C5 C10 126.8(10) . . ?
C4 C5 Ir1 68.9(3) . . ?
C1 C5 Ir1 73.7(3) . . ?
C10 C5 Ir1 128.3(9) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N12 C11 H11A 109.5 . . ?
N12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 N12 C13 111.2(13) . . ?
C16 N12 C11 125.5(12) . . ?
C13 N12 C11 123.3(14) . . ?
C14 C13 N12 106.6(14) . . ?
C14 C13 H13 126.7 . . ?
N12 C13 H13 126.7 . . ?
C13 C14 N15 107.6(13) . . ?
C13 C14 H14 126.2 . . ?
N15 C14 H14 126.2 . . ?
C16 N15 C14 109.9(13) . . ?
C16 N15 C17 123.4(12) . . ?
C14 N15 C17 126.7(13) . . ?
N12 C16 N15 104.6(11) . . ?
N12 C16 Ir1 130.3(10) . . ?
N15 C16 Ir1 124.9(11) . . ?
N15 C17 C38 110.8(12) . . ?
N15 C17 H17A 109.5 . . ?
C38 C17 H17A 109.5 . . ?
N15 C17 H17B 109.5 . . ?
C38 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C22 C21 C38 114.8(13) . . ?
C22 C21 Ir1 120.8(10) . . ?
C38 C21 Ir1 124.3(10) . . ?
C21 C22 C23 122.7(13) . . ?
C21 C22 H22 118.7 . . ?
C23 C22 H22 118.7 . . ?
C22 C23 C24 118.8(13) . . ?
C22 C23 C36 121.7(12) . . ?
C24 C23 C36 119.5(13) . . ?
C25 C24 C23 121.2(15) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 119.7(14) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C35 C26 C25 122.0(15) . . ?
C35 C26 C27 121.7(17) . . ?
C25 C26 C27 116.2(17) . . ?
C28 C27 C26 118.7(18) . . ?
C28 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
C27 C28 C29 124.6(16) . . ?
C27 C28 H28 117.7 . . ?
C29 C28 H28 117.7 . . ?
C30 C29 C34 121.5(18) . . ?
C30 C29 C28 122.8(15) . . ?
C34 C29 C28 115.7(16) . . ?
C31 C30 C29 121.6(16) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C30 C31 C32 120.9(17) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C33 C32 C31 117.8(18) . . ?
C33 C32 H32 121.1 . . ?
C31 C32 H32 121.1 . . ?
C32 C33 C34 122.4(15) . . ?
C32 C33 H33 118.8 . . ?
C34 C33 H33 118.8 . . ?
C33 C34 C29 115.5(17) . . ?
C33 C34 C35 123.7(15) . . ?
C29 C34 C35 120.7(17) . . ?
C26 C35 C36 117.7(16) . . ?
C26 C35 C34 117.4(15) . . ?
C36 C35 C34 124.9(16) . . ?
C37 C36 C23 114.0(12) . . ?
C37 C36 C35 126.6(14) . . ?
C23 C36 C35 119.2(13) . . ?
C38 C37 C36 123.4(14) . . ?
C38 C37 H37 118.3 . . ?
C36 C37 H37 118.3 . . ?
C37 C38 C21 123.3(13) . . ?
C37 C38 C17 116.8(12) . . ?
C21 C38 C17 119.9(12) . . ?

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
C5 C1 C2 C3 0.0 . . . . ?
C6 C1 C2 C3 -179.0(12) . . . . ?
Ir1 C1 C2 C3 -59.6(3) . . . . ?
C5 C1 C2 C7 -176.5(12) . . . . ?
C6 C1 C2 C7 4.5(15) . . . . ?
Ir1 C1 C2 C7 123.9(11) . . . . ?
C5 C1 C2 Ir1 59.6(3) . . . . ?
C6 C1 C2 Ir1 -119.4(11) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C7 C2 C3 C4 176.3(13) . . . . ?
Ir1 C2 C3 C4 -61.8(3) . . . . ?
C1 C2 C3 C8 -175.5(13) . . . . ?
C7 C2 C3 C8 0.8(16) . . . . ?
Ir1 C2 C3 C8 122.6(12) . . . . ?
C1 C2 C3 Ir1 61.8(3) . . . . ?
C7 C2 C3 Ir1 -121.9(12) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C8 C3 C4 C5 175.7(12) . . . . ?
Ir1 C3 C4 C5 -64.6(4) . . . . ?
C2 C3 C4 C9 -169.4(12) . . . . ?
C8 C3 C4 C9 6.3(16) . . . . ?
Ir1 C3 C4 C9 126.0(12) . . . . ?
C2 C3 C4 Ir1 64.6(4) . . . . ?
C8 C3 C4 Ir1 -119.8(11) . . . . ?
C3 C4 C5 C1 0.0 . . . . ?
C9 C4 C5 C1 169.5(12) . . . . ?
Ir1 C4 C5 C1 -63.9(4) . . . . ?
C3 C4 C5 C10 -173.3(12) . . . . ?
C9 C4 C5 C10 -3.8(15) . . . . ?
Ir1 C4 C5 C10 122.8(11) . . . . ?
C3 C4 C5 Ir1 63.9(4) . . . . ?
C9 C4 C5 Ir1 -126.6(11) . . . . ?
C2 C1 C5 C4 0.0 . . . . ?
C6 C1 C5 C4 179.0(12) . . . . ?
Ir1 C1 C5 C4 60.8(3) . . . . ?
C2 C1 C5 C10 173.2(12) . . . . ?
C6 C1 C5 C10 -7.9(15) . . . . ?
Ir1 C1 C5 C10 -126.1(11) . . . . ?
C2 C1 C5 Ir1 -60.8(3) . . . . ?
C6 C1 C5 Ir1 118.2(11) . . . . ?
C16 N12 C13 C14 -0.4(18) . . . . ?
C11 N12 C13 C14 178.7(15) . . . . ?
N12 C13 C14 N15 -0.4(18) . . . . ?
C13 C14 N15 C16 1.0(17) . . . . ?
C13 C14 N15 C17 -178.6(14) . . . . ?
C13 N12 C16 N15 0.9(16) . . . . ?
C11 N12 C16 N15 -178.2(14) . . . . ?
C13 N12 C16 Ir1 175.4(11) . . . . ?
C11 N12 C16 Ir1 -4(2) . . . . ?
C14 N15 C16 N12 -1.1(15) . . . . ?
C17 N15 C16 N12 178.4(12) . . . . ?
C14 N15 C16 Ir1 -176.0(10) . . . . ?
C17 N15 C16 Ir1 3.6(19) . . . . ?
C16 N15 C17 C38 47.2(18) . . . . ?
C14 N15 C17 C38 -133.3(14) . . . . ?
C38 C21 C22 C23 -2(2) . . . . ?
Ir1 C21 C22 C23 175.5(10) . . . . ?
C21 C22 C23 C24 -175.3(13) . . . . ?
C21 C22 C23 C36 2(2) . . . . ?
C22 C23 C24 C25 173.1(13) . . . . ?
C36 C23 C24 C25 -4(2) . . . . ?
C23 C24 C25 C26 2(2) . . . . ?
C24 C25 C26 C35 5(2) . . . . ?
C24 C25 C26 C27 -172.6(14) . . . . ?
C35 C26 C27 C28 0(2) . . . . ?
C25 C26 C27 C28 177.3(15) . . . . ?
C26 C27 C28 C29 8(3) . . . . ?
C27 C28 C29 C30 172.8(16) . . . . ?
C27 C28 C29 C34 -5(2) . . . . ?
C34 C29 C30 C31 2(3) . . . . ?
C28 C29 C30 C31 -175.6(15) . . . . ?
C29 C30 C31 C32 3(3) . . . . ?
C30 C31 C32 C33 -3(2) . . . . ?
C31 C32 C33 C34 -1(2) . . . . ?
C32 C33 C34 C29 6(2) . . . . ?
C32 C33 C34 C35 -177.0(15) . . . . ?
C30 C29 C34 C33 -6(2) . . . . ?
C28 C29 C34 C33 171.4(14) . . . . ?
C30 C29 C34 C35 176.6(15) . . . . ?
C28 C29 C34 C35 -6(2) . . . . ?
C25 C26 C35 C36 -9(2) . . . . ?
C27 C26 C35 C36 167.8(15) . . . . ?
C25 C26 C35 C34 173.0(14) . . . . ?
C27 C26 C35 C34 -10(2) . . . . ?
C33 C34 C35 C26 -164.1(15) . . . . ?
C29 C34 C35 C26 13(2) . . . . ?
C33 C34 C35 C36 18(2) . . . . ?
C29 C34 C35 C36 -164.7(15) . . . . ?
C22 C23 C36 C37 -2.5(18) . . . . ?
C24 C23 C36 C37 174.9(12) . . . . ?
C22 C23 C36 C35 -177.9(13) . . . . ?
C24 C23 C36 C35 -1(2) . . . . ?
C26 C35 C36 C37 -167.7(14) . . . . ?
C34 C35 C36 C37 10(2) . . . . ?
C26 C35 C36 C23 7(2) . . . . ?
C34 C35 C36 C23 -175.3(14) . . . . ?
C23 C36 C37 C38 3(2) . . . . ?
C35 C36 C37 C38 178.5(14) . . . . ?
C36 C37 C38 C21 -4(2) . . . . ?
C36 C37 C38 C17 176.3(14) . . . . ?
C22 C21 C38 C37 3(2) . . . . ?
Ir1 C21 C38 C37 -174.5(11) . . . . ?
C22 C21 C38 C17 -177.2(14) . . . . ?
Ir1 C21 C38 C17 5(2) . . . . ?
N15 C17 C38 C37 129.2(14) . . . . ?
N15 C17 C38 C21 -50.4(19) . . . . ?

#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR NH323                                                #
#----------------------------------------------------------------------------#
