# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

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

data_1TP
_audit_block_doi                 10.5517/ccdc.csd.cc1ky8sk
_database_code_depnum_ccdc_archive 'CCDC 1458109'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.jorganchem.2016.10.028 2016
_audit_update_record             
;
2016-03-07 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        1TP
_chemical_name_common            1TP
_chemical_melting_point          ?
_chemical_formula_moiety         C42H58B20
_chemical_formula_sum            'C42 H58 B20'
_chemical_formula_weight         779.08

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.8120(14)
_cell_length_b                   8.8274(15)
_cell_length_c                   16.566(2)
_cell_angle_alpha                92.668(10)
_cell_angle_beta                 97.662(10)
_cell_angle_gamma                112.396(9)
_cell_volume                     1174.1(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4099
_cell_measurement_theta_min      1.247
_cell_measurement_theta_max      25.242

_exptl_crystal_description       Cubic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_F_000             410
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.055
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14244
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.247
_diffrn_reflns_theta_max         25.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             4099
_reflns_number_gt                2631
_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       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1539P)²+0.4853P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4099
_refine_ls_number_parameters     361
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0817
_refine_ls_wR_factor_ref         0.2853
_refine_ls_wR_factor_gt          0.2345
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6904(4) 0.5738(4) 0.16540(16) 0.0544(8) Uani 1 1 d . . . . .
C2 C 0.7343(4) 0.6060(4) 0.27137(17) 0.0563(8) Uani 1 1 d . . . . .
C3 C 0.8407(4) 0.5281(4) 0.31636(17) 0.0585(8) Uani 1 1 d . . . . .
C4 C 0.7766(5) 0.3653(5) 0.3319(2) 0.0816(11) Uani 1 1 d . . . . .
C5 C 0.8774(7) 0.2980(6) 0.3748(3) 0.0985(14) Uani 1 1 d . . . . .
C6 C 1.0432(6) 0.3892(6) 0.4049(2) 0.0849(12) Uani 1 1 d . . . . .
C7 C 1.1064(5) 0.5510(6) 0.3887(3) 0.0909(12) Uani 1 1 d . . . . .
C8 C 1.0086(5) 0.6201(5) 0.3452(2) 0.0777(10) Uani 1 1 d . . . . .
C9 C 0.7555(3) 0.4611(4) 0.12428(16) 0.0509(7) Uani 1 1 d . . . . .
C10 C 0.9244(4) 0.5065(4) 0.1215(2) 0.0640(9) Uani 1 1 d . . . . .
C11 C 0.9825(4) 0.3977(4) 0.0885(2) 0.0635(9) Uani 1 1 d . . . . .
C12 C 0.8767(4) 0.2393(4) 0.05713(17) 0.0546(8) Uani 1 1 d . . . . .
C13 C 0.7072(4) 0.1967(4) 0.0568(2) 0.0612(8) Uani 1 1 d . . . . .
C14 C 0.6481(4) 0.3048(4) 0.08995(19) 0.0611(8) Uani 1 1 d . . . . .
C15 C 0.9414(4) 0.1187(4) 0.02653(18) 0.0559(8) Uani 1 1 d . . . . .
C16 C 1.0775(4) 0.1001(4) 0.07250(19) 0.0601(8) Uani 1 1 d . . . . .
C17 C 0.8656(4) 0.0166(4) -0.04610(18) 0.0608(8) Uani 1 1 d . . . . .
C18 C 1.1522(7) 0.3124(8) 0.4484(3) 0.1272(19) Uani 1 1 d . . . . .
H18A H 1.0913 0.2390 0.4853 0.153 Uiso 1 1 calc R U . . .
H18B H 1.2489 0.3983 0.4811 0.153 Uiso 1 1 calc R U . . .
C19 C 1.2090(7) 0.2170(7) 0.3900(5) 0.155(3) Uani 1 1 d D . . . .
H19A H 1.2711 0.2896 0.3532 0.186 Uiso 1 1 calc R U . . .
H19B H 1.1132 0.1298 0.3575 0.186 Uiso 1 1 calc R U . . .
C20 C 1.3242(14) 0.1392(14) 0.4408(8) 0.264(5) Uani 1 1 d D U . . .
H20A H 1.4283 0.2221 0.4694 0.317 Uiso 1 1 calc R U . . .
H20B H 1.2673 0.0650 0.4784 0.317 Uiso 1 1 calc R U . . .
C21 C 1.345(3) 0.051(2) 0.3671(13) 0.459(12) Uani 1 1 d D U . . .
H21A H 1.4609 0.0918 0.3621 0.689 Uiso 1 1 calc R U . . .
H21B H 1.2832 0.0703 0.3192 0.689 Uiso 1 1 calc R U . . .
H21C H 1.3053 -0.0645 0.3724 0.689 Uiso 1 1 calc R U . . .
H1 H 1.135(4) 0.168(4) 0.1260(19) 0.061(8) Uiso 1 1 d . . . . .
H2 H 0.772(4) 0.027(4) -0.0776(19) 0.064(9) Uiso 1 1 d . . . . .
H3 H 1.096(5) 0.435(5) 0.090(2) 0.086(11) Uiso 1 1 d . . . . .
H4 H 0.636(4) 0.089(5) 0.034(2) 0.082(11) Uiso 1 1 d . . . . .
H5 H 1.002(4) 0.607(4) 0.143(2) 0.077(11) Uiso 1 1 d . . . . .
H6 H 0.532(4) 0.276(4) 0.086(2) 0.076(10) Uiso 1 1 d . . . . .
H7 H 1.237(6) 0.628(5) 0.410(3) 0.112(14) Uiso 1 1 d . . . . .
H8 H 0.832(6) 0.188(6) 0.392(3) 0.121(15) Uiso 1 1 d . . . . .
H9 H 1.057(5) 0.735(5) 0.338(2) 0.087(12) Uiso 1 1 d . . . . .
H10 H 0.662(6) 0.297(5) 0.314(3) 0.114(15) Uiso 1 1 d . . . . .
B1 B 0.4958(5) 0.5708(6) 0.1327(2) 0.0719(11) Uani 1 1 d . . . . .
B2 B 0.6789(6) 0.7461(5) 0.1267(2) 0.0727(11) Uani 1 1 d . . . . .
B3 B 0.5088(7) 0.7711(7) 0.1643(3) 0.0935(16) Uani 1 1 d . . . . .
B4 B 0.4196(6) 0.6062(7) 0.2231(3) 0.0858(14) Uani 1 1 d . . . . .
B5 B 0.5349(5) 0.4809(6) 0.2233(2) 0.0654(10) Uani 1 1 d . . . . .
B6 B 0.8297(5) 0.7628(5) 0.2133(2) 0.0637(10) Uani 1 1 d . . . . .
B7 B 0.7160(7) 0.8900(6) 0.2132(3) 0.0827(13) Uani 1 1 d . . . . .
B8 B 0.5540(7) 0.8044(7) 0.2723(3) 0.0890(15) Uani 1 1 d . . . . .
B9 B 0.5703(5) 0.6253(6) 0.3093(2) 0.0731(12) Uani 1 1 d . . . . .
B10 B 0.7526(6) 0.7995(5) 0.3032(2) 0.0702(11) Uani 1 1 d . . . . .
H101 H 0.426(4) 0.476(4) 0.077(2) 0.073(9) Uiso 1 1 d . . . . .
H102 H 0.485(4) 0.339(4) 0.2238(19) 0.073(9) Uiso 1 1 d . . . . .
H103 H 0.286(5) 0.540(4) 0.225(2) 0.092(11) Uiso 1 1 d . . . . .
H104 H 0.426(5) 0.819(5) 0.129(2) 0.104(12) Uiso 1 1 d . . . . .
H105 H 0.715(4) 0.764(4) 0.069(2) 0.081(10) Uiso 1 1 d . . . . .
H106 H 0.964(4) 0.798(3) 0.2084(17) 0.058(8) Uiso 1 1 d . . . . .
H107 H 0.784(5) 1.023(6) 0.205(3) 0.127(15) Uiso 1 1 d . . . . .
H108 H 0.517(4) 0.896(4) 0.317(2) 0.090(11) Uiso 1 1 d . . . . .
H109 H 0.546(4) 0.581(4) 0.365(2) 0.076(9) Uiso 1 1 d . . . . .
H110 H 0.834(4) 0.861(4) 0.359(2) 0.075(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.503(4) . ?
C1 B2 1.711(5) . ?
C1 B1 1.718(5) . ?
C1 B6 1.725(5) . ?
C1 C2 1.732(4) . ?
C1 B5 1.742(5) . ?
C2 C3 1.503(4) . ?
C2 B10 1.705(5) . ?
C2 B9 1.712(5) . ?
C2 B6 1.733(5) . ?
C2 B5 1.734(5) . ?
C3 C4 1.380(5) . ?
C3 C8 1.392(5) . ?
C4 C5 1.386(5) . ?
C5 C6 1.380(6) . ?
C6 C7 1.376(6) . ?
C6 C18 1.503(5) . ?
C7 C8 1.382(5) . ?
C9 C14 1.382(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.373(4) . ?
C11 C12 1.380(4) . ?
C12 C13 1.394(4) . ?
C12 C15 1.484(4) . ?
C13 C14 1.375(4) . ?
C15 C17 1.390(4) . ?
C15 C16 1.401(4) . ?
C16 C17 1.384(4) 2_755 ?
C17 C16 1.384(4) 2_755 ?
C18 C19 1.507(8) . ?
C19 C20 1.602(10) . ?
C20 C21 1.485(15) . ?
B1 B3 1.776(7) . ?
B1 B2 1.778(7) . ?
B1 B4 1.782(5) . ?
B1 B5 1.784(5) . ?
B2 B3 1.780(6) . ?
B2 B7 1.779(6) . ?
B2 B6 1.780(6) . ?
B3 B8 1.766(6) . ?
B3 B4 1.774(8) . ?
B3 B7 1.777(8) . ?
B4 B5 1.764(6) . ?
B4 B9 1.770(6) . ?
B4 B8 1.777(8) . ?
B5 B9 1.779(6) . ?
B6 B7 1.767(5) . ?
B6 B10 1.783(5) . ?
B7 B10 1.773(6) . ?
B7 B8 1.785(7) . ?
B8 B9 1.770(7) . ?
B8 B10 1.775(6) . ?
B9 B10 1.770(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 B2 124.3(2) . . ?
C9 C1 B1 122.1(3) . . ?
B2 C1 B1 62.5(2) . . ?
C9 C1 B6 119.0(2) . . ?
B2 C1 B6 62.4(2) . . ?
B1 C1 B6 113.1(3) . . ?
C9 C1 C2 117.0(2) . . ?
B2 C1 C2 109.8(2) . . ?
B1 C1 C2 109.5(2) . . ?
B6 C1 C2 60.16(18) . . ?
C9 C1 B5 115.9(3) . . ?
B2 C1 B5 112.8(3) . . ?
B1 C1 B5 62.0(2) . . ?
B6 C1 B5 111.3(2) . . ?
C2 C1 B5 59.88(18) . . ?
C3 C2 B10 121.0(3) . . ?
C3 C2 B9 122.0(2) . . ?
B10 C2 B9 62.4(2) . . ?
C3 C2 C1 119.0(2) . . ?
B10 C2 C1 109.7(2) . . ?
B9 C2 C1 109.9(2) . . ?
C3 C2 B6 117.3(3) . . ?
B10 C2 B6 62.5(2) . . ?
B9 C2 B6 113.1(3) . . ?
C1 C2 B6 59.72(19) . . ?
C3 C2 B5 118.9(3) . . ?
B10 C2 B5 112.9(3) . . ?
B9 C2 B5 62.1(2) . . ?
C1 C2 B5 60.34(18) . . ?
B6 C2 B5 111.3(2) . . ?
C4 C3 C8 117.5(3) . . ?
C4 C3 C2 121.9(3) . . ?
C8 C3 C2 120.5(3) . . ?
C3 C4 C5 120.5(4) . . ?
C6 C5 C4 122.3(4) . . ?
C7 C6 C5 116.8(4) . . ?
C7 C6 C18 121.5(5) . . ?
C5 C6 C18 121.5(5) . . ?
C6 C7 C8 121.8(4) . . ?
C7 C8 C3 121.0(4) . . ?
C14 C9 C10 117.6(3) . . ?
C14 C9 C1 120.3(3) . . ?
C10 C9 C1 122.0(3) . . ?
C11 C10 C9 121.1(3) . . ?
C10 C11 C12 121.5(3) . . ?
C11 C12 C13 117.2(3) . . ?
C11 C12 C15 121.3(3) . . ?
C13 C12 C15 121.5(3) . . ?
C14 C13 C12 121.6(3) . . ?
C13 C14 C9 120.9(3) . . ?
C17 C15 C16 118.0(3) . . ?
C17 C15 C12 121.6(3) . . ?
C16 C15 C12 120.3(3) . . ?
C17 C16 C15 120.8(3) 2_755 . ?
C16 C17 C15 121.2(3) 2_755 . ?
C6 C18 C19 112.4(4) . . ?
C18 C19 C20 109.5(7) . . ?
C21 C20 C19 94.3(11) . . ?
C1 B1 B3 105.2(3) . . ?
C1 B1 B2 58.5(2) . . ?
B3 B1 B2 60.1(3) . . ?
C1 B1 B4 105.8(3) . . ?
B3 B1 B4 59.8(3) . . ?
B2 B1 B4 108.0(3) . . ?
C1 B1 B5 59.64(19) . . ?
B3 B1 B5 107.0(3) . . ?
B2 B1 B5 107.7(3) . . ?
B4 B1 B5 59.3(2) . . ?
C1 B2 B1 59.0(2) . . ?
C1 B2 B3 105.4(3) . . ?
B1 B2 B3 59.9(3) . . ?
C1 B2 B7 105.7(3) . . ?
B1 B2 B7 108.0(3) . . ?
B3 B2 B7 59.9(3) . . ?
C1 B2 B6 59.2(2) . . ?
B1 B2 B6 107.7(3) . . ?
B3 B2 B6 107.2(3) . . ?
B7 B2 B6 59.5(2) . . ?
B8 B3 B4 60.3(3) . . ?
B8 B3 B7 60.5(3) . . ?
B4 B3 B7 108.3(3) . . ?
B8 B3 B1 108.8(3) . . ?
B4 B3 B1 60.3(3) . . ?
B7 B3 B1 108.2(3) . . ?
B8 B3 B2 108.8(3) . . ?
B4 B3 B2 108.3(3) . . ?
B7 B3 B2 60.0(3) . . ?
B1 B3 B2 60.0(2) . . ?
B5 B4 B9 60.4(2) . . ?
B5 B4 B3 107.9(3) . . ?
B9 B4 B3 107.7(4) . . ?
B5 B4 B8 108.2(3) . . ?
B9 B4 B8 59.9(3) . . ?
B3 B4 B8 59.6(3) . . ?
B5 B4 B1 60.4(2) . . ?
B9 B4 B1 108.8(3) . . ?
B3 B4 B1 59.9(3) . . ?
B8 B4 B1 108.1(4) . . ?
C2 B5 C1 59.77(18) . . ?
C2 B5 B4 105.4(3) . . ?
C1 B5 B4 105.5(3) . . ?
C2 B5 B9 58.3(2) . . ?
C1 B5 B9 106.4(3) . . ?
B4 B5 B9 59.9(2) . . ?
C2 B5 B1 106.4(3) . . ?
C1 B5 B1 58.3(2) . . ?
B4 B5 B1 60.3(2) . . ?
B9 B5 B1 108.3(3) . . ?
C1 B6 C2 60.12(19) . . ?
C1 B6 B7 105.6(3) . . ?
C2 B6 B7 105.2(3) . . ?
C1 B6 B2 58.4(2) . . ?
C2 B6 B2 106.6(3) . . ?
B7 B6 B2 60.2(2) . . ?
C1 B6 B10 106.4(3) . . ?
C2 B6 B10 58.0(2) . . ?
B7 B6 B10 59.9(2) . . ?
B2 B6 B10 108.2(3) . . ?
B6 B7 B10 60.5(2) . . ?
B6 B7 B3 107.9(3) . . ?
B10 B7 B3 107.5(4) . . ?
B6 B7 B2 60.2(2) . . ?
B10 B7 B2 108.7(3) . . ?
B3 B7 B2 60.1(3) . . ?
B6 B7 B8 108.2(3) . . ?
B10 B7 B8 59.8(3) . . ?
B3 B7 B8 59.5(3) . . ?
B2 B7 B8 108.1(4) . . ?
B3 B8 B9 108.0(3) . . ?
B3 B8 B10 107.9(3) . . ?
B9 B8 B10 59.9(2) . . ?
B3 B8 B4 60.1(3) . . ?
B9 B8 B4 59.8(3) . . ?
B10 B8 B4 107.7(3) . . ?
B3 B8 B7 60.0(3) . . ?
B9 B8 B7 107.7(3) . . ?
B10 B8 B7 59.8(3) . . ?
B4 B8 B7 107.8(3) . . ?
C2 B9 B10 58.6(2) . . ?
C2 B9 B8 105.8(3) . . ?
B10 B9 B8 60.2(3) . . ?
C2 B9 B4 106.1(3) . . ?
B10 B9 B4 108.2(3) . . ?
B8 B9 B4 60.3(3) . . ?
C2 B9 B5 59.54(19) . . ?
B10 B9 B5 107.7(3) . . ?
B8 B9 B5 107.8(3) . . ?
B4 B9 B5 59.6(2) . . ?
C2 B10 B9 59.0(2) . . ?
C2 B10 B7 106.1(3) . . ?
B9 B10 B7 108.3(3) . . ?
C2 B10 B8 105.9(3) . . ?
B9 B10 B8 59.9(3) . . ?
B7 B10 B8 60.4(3) . . ?
C2 B10 B6 59.53(19) . . ?
B9 B10 B6 108.0(3) . . ?
B7 B10 B6 59.6(2) . . ?
B8 B10 B6 107.9(3) . . ?

_refine_diff_density_max         0.672
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_CNIr
_audit_block_doi                 10.5517/ccdc.csd.cc1q0mcq
_database_code_depnum_ccdc_archive 'CCDC 1579523'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        CNIr
_chemical_name_common            CNIr
_chemical_melting_point          ?
_chemical_formula_moiety         C66H66IrN9
_chemical_formula_sum            'C66 H66 Ir N9'
_chemical_formula_weight         1177.47

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'
Ir Ir -1.4442 7.9887 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.985(3)
_cell_length_b                   26.651(5)
_cell_length_c                   17.246(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.60(3)
_cell_angle_gamma                90
_cell_volume                     6721(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    247154
_cell_measurement_theta_min      2.068
_cell_measurement_theta_max      28.356

_exptl_crystal_description       cubic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             2408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.028
_shelx_estimated_absorpt_T_min   0.700
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            247154
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.1033
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.068
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             16757
_reflns_number_gt                12326
_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       'Bruker D8 QUEST'
_computing_cell_refinement       'Bruker D8 QUEST'
_computing_data_reduction        'Bruker D8 QUEST'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1300P)²+0.0041P] 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         16757
_refine_ls_number_parameters     697
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1544
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_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 1.00467(2) 0.29171(2) 0.26525(2) 0.03051(9) Uani 1 1 d . . . . .
N1 N 1.0573(3) 0.25162(17) 0.3720(2) 0.0357(9) Uani 1 1 d . . . . .
N2 N 1.1744(3) 0.22995(17) 0.4641(2) 0.0360(9) Uani 1 1 d . . . . .
N3 N 0.8641(3) 0.28051(17) 0.2620(3) 0.0353(9) Uani 1 1 d . . . . .
C1 C 1.1400(3) 0.29491(17) 0.2688(3) 0.0278(10) Uani 1 1 d . . . . .
C2 C 1.1847(3) 0.31840(18) 0.2152(3) 0.0330(10) Uani 1 1 d . . . . .
H18 H 1.1496 0.3345 0.1712 0.040 Uiso 1 1 calc R U . . .
C3 C 1.2783(3) 0.3186(2) 0.2249(3) 0.0375(11) Uani 1 1 d . . . . .
H19 H 1.3052 0.3350 0.1882 0.045 Uiso 1 1 calc R U . . .
C4 C 1.3331(3) 0.2943(2) 0.2901(3) 0.0383(12) Uani 1 1 d . . . . .
C5 C 1.2926(3) 0.2711(2) 0.3458(3) 0.0375(11) Uani 1 1 d . . . . .
H21 H 1.3286 0.2553 0.3898 0.045 Uiso 1 1 calc R U . . .
C6 C 1.1981(3) 0.27155(19) 0.3355(3) 0.0304(9) Uani 1 1 d . . . . .
C7 C 1.1472(3) 0.25042(19) 0.3906(3) 0.0330(10) Uani 1 1 d . . . . .
C8 C 1.0243(3) 0.2318(2) 0.4329(3) 0.0443(13) Uani 1 1 d . . . . .
H14 H 0.9630 0.2282 0.4342 0.053 Uiso 1 1 calc R U . . .
C9 C 1.0964(4) 0.2184(2) 0.4911(3) 0.0455(14) Uani 1 1 d . . . . .
H13 H 1.0940 0.2041 0.5398 0.055 Uiso 1 1 calc R U . . .
C10 C 1.2663(3) 0.2216(2) 0.5083(3) 0.0363(11) Uani 1 1 d . . . . .
C11 C 1.3083(3) 0.2592(2) 0.5616(3) 0.0373(11) Uani 1 1 d . . . . .
C12 C 1.3971(3) 0.2501(2) 0.6024(3) 0.0474(13) Uani 1 1 d . . . . .
H5 H 1.4277 0.2745 0.6368 0.057 Uiso 1 1 calc R U . . .
C13 C 1.4409(4) 0.2059(2) 0.5932(4) 0.0502(15) Uani 1 1 d . . . . .
H4 H 1.5002 0.2005 0.6220 0.060 Uiso 1 1 calc R U . . .
C14 C 1.3980(4) 0.1697(2) 0.5419(4) 0.0529(15) Uani 1 1 d . . . . .
H3 H 1.4285 0.1399 0.5367 0.063 Uiso 1 1 calc R U . . .
C15 C 1.3095(4) 0.1767(2) 0.4975(3) 0.0435(12) Uani 1 1 d . . . . .
C16 C 1.2595(4) 0.3080(2) 0.5734(4) 0.0453(12) Uani 1 1 d . . . . .
H70 H 1.1936 0.3018 0.5573 0.054 Uiso 1 1 calc R U . . .
C17 C 1.2828(5) 0.3499(2) 0.5207(4) 0.0643(18) Uani 1 1 d . . . . .
H9A H 1.2523 0.3802 0.5303 0.096 Uiso 1 1 calc R U . . .
H9B H 1.2631 0.3405 0.4659 0.096 Uiso 1 1 calc R U . . .
H9C H 1.3477 0.3553 0.5329 0.096 Uiso 1 1 calc R U . . .
C18 C 1.2800(4) 0.3237(2) 0.6598(4) 0.0562(15) Uani 1 1 d . . . . .
H8A H 1.2717 0.2956 0.6922 0.084 Uiso 1 1 calc R U . . .
H8B H 1.2394 0.3503 0.6670 0.084 Uiso 1 1 calc R U . . .
H8C H 1.3421 0.3352 0.6749 0.084 Uiso 1 1 calc R U . . .
C19 C 1.2622(5) 0.1367(2) 0.4409(4) 0.0622(17) Uani 1 1 d . . . . .
H10 H 1.2076 0.1518 0.4072 0.075 Uiso 1 1 calc R U . . .
C20 C 1.2319(8) 0.0946(3) 0.4852(7) 0.127(4) Uani 1 1 d . . . . .
H68A H 1.2837 0.0744 0.5087 0.190 Uiso 1 1 calc R U . . .
H68B H 1.1881 0.0745 0.4494 0.190 Uiso 1 1 calc R U . . .
H68C H 1.2043 0.1078 0.5262 0.190 Uiso 1 1 calc R U . . .
C21 C 1.3232(6) 0.1181(4) 0.3871(6) 0.111(4) Uani 1 1 d . . . . .
H69A H 1.3694 0.0964 0.4167 0.167 Uiso 1 1 calc R U . . .
H69B H 1.3517 0.1463 0.3676 0.167 Uiso 1 1 calc R U . . .
H69C H 1.2870 0.1000 0.3432 0.167 Uiso 1 1 calc R U . . .
N4 N 0.7341(2) 0.24433(18) 0.2048(2) 0.0385(10) Uani 1 1 d . . . . .
N5 N 1.0162(3) 0.36038(17) 0.3257(2) 0.0366(9) Uani 1 1 d . . . . .
N6 N 1.0193(3) 0.44343(19) 0.3212(3) 0.0528(12) Uani 1 1 d . . . . .
C22 C 0.9801(3) 0.2296(2) 0.1979(3) 0.0323(10) Uani 1 1 d . . . . .
C23 C 1.0424(4) 0.20164(19) 0.1645(4) 0.0390(12) Uani 1 1 d . . . . .
H40 H 1.1030 0.2121 0.1739 0.047 Uiso 1 1 calc R U . . .
C24 C 1.0173(4) 0.1599(2) 0.1190(3) 0.0436(12) Uani 1 1 d . . . . .
H41 H 1.0605 0.1431 0.0973 0.052 Uiso 1 1 calc R U . . .
C25 C 0.9273(4) 0.1424(2) 0.1047(3) 0.0402(11) Uani 1 1 d . . . . .
C26 C 0.8625(3) 0.1679(2) 0.1366(3) 0.0401(11) Uani 1 1 d . . . . .
H37 H 0.8027 0.1562 0.1279 0.048 Uiso 1 1 calc R U . . .
C27 C 0.8882(3) 0.21113(18) 0.1815(3) 0.0353(11) Uani 1 1 d . . . . .
C28 C 0.8277(3) 0.2429(2) 0.2151(3) 0.0360(11) Uani 1 1 d . . . . .
C29 C 0.7934(4) 0.3072(2) 0.2817(3) 0.0419(12) Uani 1 1 d . . . . .
H36 H 0.7994 0.3359 0.3132 0.050 Uiso 1 1 calc R U . . .
C30 C 0.7131(4) 0.2843(2) 0.2470(3) 0.0421(13) Uani 1 1 d . . . . .
H35 H 0.6548 0.2941 0.2514 0.051 Uiso 1 1 calc R U . . .
C31 C 0.6702(3) 0.2135(2) 0.1504(3) 0.0422(13) Uani 1 1 d . . . . .
C32 C 0.6233(3) 0.1761(2) 0.1813(3) 0.0457(13) Uani 1 1 d . . . . .
C33 C 0.5655(4) 0.1457(3) 0.1266(4) 0.0617(17) Uani 1 1 d . . . . .
H31 H 0.5345 0.1194 0.1447 0.074 Uiso 1 1 calc R U . . .
C34 C 0.5533(4) 0.1538(3) 0.0451(4) 0.071(2) Uani 1 1 d . . . . .
H30 H 0.5132 0.1337 0.0095 0.085 Uiso 1 1 calc R U . . .
C35 C 0.5995(5) 0.1908(3) 0.0178(4) 0.073(2) Uani 1 1 d . . . . .
H29 H 0.5909 0.1956 -0.0367 0.087 Uiso 1 1 calc R U . . .
C36 C 0.6598(4) 0.2223(3) 0.0691(4) 0.0553(16) Uani 1 1 d . . . . .
C37 C 0.6346(4) 0.1681(2) 0.2698(3) 0.0500(13) Uani 1 1 d . . . . .
H23 H 0.6503 0.2007 0.2956 0.060 Uiso 1 1 calc R U . . .
C38 C 0.7165(6) 0.1321(3) 0.3012(5) 0.095(3) Uani 1 1 d . . . . .
H24A H 0.7034 0.0996 0.2773 0.142 Uiso 1 1 calc R U . . .
H24B H 0.7258 0.1290 0.3579 0.142 Uiso 1 1 calc R U . . .
H24C H 0.7708 0.1453 0.2879 0.142 Uiso 1 1 calc R U . . .
C39 C 0.5485(5) 0.1502(3) 0.2927(4) 0.080(2) Uani 1 1 d . . . . .
H25A H 0.4978 0.1703 0.2662 0.120 Uiso 1 1 calc R U . . .
H25B H 0.5552 0.1532 0.3491 0.120 Uiso 1 1 calc R U . . .
H25C H 0.5376 0.1158 0.2773 0.120 Uiso 1 1 calc R U . . .
C40 C 0.7089(4) 0.2646(3) 0.0369(3) 0.0642(19) Uani 1 1 d . . . . .
H32 H 0.7613 0.2744 0.0788 0.077 Uiso 1 1 calc R U . . .
C41 C 0.6495(7) 0.3089(4) 0.0166(7) 0.113(4) Uani 1 1 d . . . . .
H67A H 0.6845 0.3361 0.0020 0.169 Uiso 1 1 calc R U . . .
H67B H 0.6256 0.3185 0.0617 0.169 Uiso 1 1 calc R U . . .
H67C H 0.6000 0.3010 -0.0271 0.169 Uiso 1 1 calc R U . . .
C42 C 0.7459(5) 0.2476(4) -0.0359(4) 0.092(3) Uani 1 1 d . . . . .
H34A H 0.6957 0.2429 -0.0805 0.138 Uiso 1 1 calc R U . . .
H34B H 0.7785 0.2165 -0.0238 0.138 Uiso 1 1 calc R U . . .
H34C H 0.7864 0.2727 -0.0484 0.138 Uiso 1 1 calc R U . . .
N7 N 1.5073(3) 0.2928(2) 0.3067(4) 0.072(2) Uani 1 1 d . . . . .
N8 N 0.8840(5) 0.0619(3) 0.0220(4) 0.089(2) Uani 1 1 d . . . . .
N9 N 0.8691(11) 0.4834(4) -0.0504(5) 0.202(7) Uani 1 1 d . . . . .
C43 C 0.9693(3) 0.3394(2) 0.1732(3) 0.0332(10) Uani 1 1 d . . . . .
C44 C 0.9387(3) 0.3280(2) 0.0925(3) 0.0402(12) Uani 1 1 d . . . . .
H61 H 0.9342 0.2945 0.0769 0.048 Uiso 1 1 calc R U . . .
C45 C 0.9148(5) 0.3651(2) 0.0347(3) 0.0527(16) Uani 1 1 d . . . . .
H60 H 0.8949 0.3561 -0.0184 0.063 Uiso 1 1 calc R U . . .
C46 C 0.9205(5) 0.4146(3) 0.0558(4) 0.069(2) Uani 1 1 d . . . . .
C47 C 0.9489(5) 0.4280(3) 0.1349(3) 0.0590(17) Uani 1 1 d . . . . .
H58 H 0.9519 0.4617 0.1496 0.071 Uiso 1 1 calc R U . . .
C48 C 0.9729(4) 0.3907(2) 0.1927(3) 0.0427(12) Uani 1 1 d . . . . .
C49 C 1.0020(3) 0.3991(2) 0.2782(3) 0.0441(13) Uani 1 1 d . . . . .
C50 C 1.0434(4) 0.3779(3) 0.4022(3) 0.0523(15) Uani 1 1 d . . . . .
H55 H 1.0574 0.3582 0.4478 0.063 Uiso 1 1 calc R U . . .
C51 C 1.0463(5) 0.4294(3) 0.3999(4) 0.0647(19) Uani 1 1 d . . . . .
H54 H 1.0633 0.4508 0.4433 0.078 Uiso 1 1 calc R U . . .
C52 C 1.0138(4) 0.4929(2) 0.2886(4) 0.0527(15) Uani 1 1 d . . . . .
C53 C 0.9320(5) 0.5187(2) 0.2812(4) 0.0503(14) Uani 1 1 d . . . . .
C54 C 0.9242(6) 0.5640(3) 0.2431(5) 0.071(2) Uani 1 1 d . . . . .
H49 H 0.8697 0.5818 0.2351 0.085 Uiso 1 1 calc R U . . .
C55 C 0.9994(9) 0.5833(4) 0.2162(5) 0.102(4) Uani 1 1 d . . . . .
H50 H 0.9956 0.6144 0.1913 0.123 Uiso 1 1 calc R U . . .
C56 C 1.0803(9) 0.5549(5) 0.2277(7) 0.110(4) Uani 1 1 d . . . . .
H51 H 1.1296 0.5674 0.2090 0.132 Uiso 1 1 calc R U . . .
C57 C 1.0887(6) 0.5106(4) 0.2644(6) 0.084(3) Uani 1 1 d . . . . .
C58 C 0.8534(5) 0.4965(3) 0.3116(4) 0.0631(17) Uani 1 1 d . . . . .
H47 H 0.8793 0.4680 0.3448 0.076 Uiso 1 1 calc R U . . .
C59 C 0.8186(7) 0.5325(3) 0.3672(6) 0.111(4) Uani 1 1 d . . . . .
H48A H 0.8685 0.5425 0.4094 0.167 Uiso 1 1 calc R U . . .
H48B H 0.7727 0.5161 0.3891 0.167 Uiso 1 1 calc R U . . .
H48C H 0.7927 0.5617 0.3379 0.167 Uiso 1 1 calc R U . . .
C60 C 0.7802(7) 0.4750(5) 0.2474(7) 0.122(4) Uani 1 1 d . . . . .
H65A H 0.7455 0.5018 0.2180 0.183 Uiso 1 1 calc R U . . .
H65B H 0.7405 0.4543 0.2706 0.183 Uiso 1 1 calc R U . . .
H65C H 0.8075 0.4552 0.2123 0.183 Uiso 1 1 calc R U . . .
C61 C 1.1806(7) 0.4826(6) 0.2834(8) 0.150(6) Uani 1 1 d . . . . .
H52 H 1.1666 0.4539 0.3144 0.179 Uiso 1 1 calc R U . . .
C62 C 1.2500(7) 0.5112(5) 0.3451(7) 0.149(5) Uani 1 1 d . . . . .
H66A H 1.3095 0.5079 0.3335 0.223 Uiso 1 1 calc R U . . .
H66B H 1.2510 0.4977 0.3969 0.223 Uiso 1 1 calc R U . . .
H66C H 1.2332 0.5460 0.3438 0.223 Uiso 1 1 calc R U . . .
C63 C 1.2082(10) 0.4600(5) 0.2244(9) 0.151(6) Uani 1 1 d . . . . .
H61A H 1.2395 0.4837 0.1979 0.226 Uiso 1 1 calc R U . . .
H61B H 1.1561 0.4469 0.1873 0.226 Uiso 1 1 calc R U . . .
H61C H 1.2489 0.4330 0.2451 0.226 Uiso 1 1 calc R U . . .
C64 C 1.4310(4) 0.2938(2) 0.2994(4) 0.0497(15) Uani 1 1 d . . . . .
C65 C 0.9016(5) 0.0984(3) 0.0583(4) 0.0616(17) Uani 1 1 d . . . . .
C66 C 0.8929(9) 0.4534(3) -0.0041(4) 0.121(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C22 2.011(5) . ?
Ir1 C43 2.013(5) . ?
Ir1 C1 2.017(5) . ?
Ir1 N5 2.094(4) . ?
Ir1 N3 2.116(4) . ?
Ir1 N1 2.125(4) . ?
N1 C7 1.315(6) . ?
N1 C8 1.361(6) . ?
N2 C7 1.359(6) . ?
N2 C9 1.384(6) . ?
N2 C10 1.439(6) . ?
N3 C28 1.328(6) . ?
N3 C29 1.379(6) . ?
C1 C2 1.402(6) . ?
C1 C6 1.426(6) . ?
C2 C3 1.376(7) . ?
C3 C4 1.398(7) . ?
C4 C5 1.389(7) . ?
C4 C64 1.441(7) . ?
C5 C6 1.388(6) . ?
C6 C7 1.455(6) . ?
C8 C9 1.354(7) . ?
C10 C15 1.394(8) . ?
C10 C11 1.409(8) . ?
C11 C12 1.384(7) . ?
C11 C16 1.528(8) . ?
C12 C13 1.376(8) . ?
C13 C14 1.370(9) . ?
C14 C15 1.392(7) . ?
C15 C19 1.512(8) . ?
C16 C18 1.513(8) . ?
C16 C17 1.527(8) . ?
C19 C20 1.482(11) . ?
C19 C21 1.521(11) . ?
N4 C30 1.366(7) . ?
N4 C28 1.375(6) . ?
N4 C31 1.441(6) . ?
N5 C49 1.306(7) . ?
N5 C50 1.376(7) . ?
N6 C51 1.381(8) . ?
N6 C49 1.389(7) . ?
N6 C52 1.428(8) . ?
C22 C23 1.410(7) . ?
C22 C27 1.431(7) . ?
C23 C24 1.365(7) . ?
C24 C25 1.398(7) . ?
C25 C26 1.392(7) . ?
C25 C65 1.425(8) . ?
C26 C27 1.396(7) . ?
C27 C28 1.451(6) . ?
C29 C30 1.366(8) . ?
C31 C32 1.391(8) . ?
C31 C36 1.398(8) . ?
C32 C33 1.394(8) . ?
C32 C37 1.514(8) . ?
C33 C34 1.394(10) . ?
C34 C35 1.348(10) . ?
C35 C36 1.397(9) . ?
C36 C40 1.515(9) . ?
C37 C39 1.507(8) . ?
C37 C38 1.559(9) . ?
C40 C41 1.474(11) . ?
C40 C42 1.546(9) . ?
N7 C64 1.124(7) . ?
N8 C65 1.155(8) . ?
N9 C66 1.130(10) . ?
C43 C44 1.400(6) . ?
C43 C48 1.406(8) . ?
C44 C45 1.394(7) . ?
C45 C46 1.368(9) . ?
C46 C47 1.384(8) . ?
C46 C66 1.457(10) . ?
C47 C48 1.398(8) . ?
C48 C49 1.461(8) . ?
C50 C51 1.373(10) . ?
C52 C57 1.364(10) . ?
C52 C53 1.387(9) . ?
C53 C54 1.365(10) . ?
C53 C58 1.511(9) . ?
C54 C55 1.406(13) . ?
C55 C56 1.406(14) . ?
C56 C57 1.333(16) . ?
C57 C61 1.539(14) . ?
C58 C60 1.493(12) . ?
C58 C59 1.526(10) . ?
C61 C63 1.323(16) . ?
C61 C62 1.520(15) . ?

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
C22 Ir1 C43 94.64(19) . . ?
C22 Ir1 C1 96.21(18) . . ?
C43 Ir1 C1 95.03(18) . . ?
C22 Ir1 N5 172.86(17) . . ?
C43 Ir1 N5 79.61(18) . . ?
C1 Ir1 N5 88.56(17) . . ?
C22 Ir1 N3 79.22(17) . . ?
C43 Ir1 N3 88.76(18) . . ?
C1 Ir1 N3 174.31(18) . . ?
N5 Ir1 N3 96.31(17) . . ?
C22 Ir1 N1 94.17(17) . . ?
C43 Ir1 N1 169.98(18) . . ?
C1 Ir1 N1 79.28(17) . . ?
N5 Ir1 N1 91.93(16) . . ?
N3 Ir1 N1 97.56(16) . . ?
C7 N1 C8 109.1(4) . . ?
C7 N1 Ir1 113.0(3) . . ?
C8 N1 Ir1 137.3(3) . . ?
C7 N2 C9 107.5(4) . . ?
C7 N2 C10 127.8(4) . . ?
C9 N2 C10 124.7(4) . . ?
C28 N3 C29 107.8(4) . . ?
C28 N3 Ir1 113.4(3) . . ?
C29 N3 Ir1 137.2(4) . . ?
C2 C1 C6 115.5(4) . . ?
C2 C1 Ir1 128.4(3) . . ?
C6 C1 Ir1 116.1(3) . . ?
C3 C2 C1 122.9(4) . . ?
C2 C3 C4 120.0(5) . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 C64 120.4(5) . . ?
C3 C4 C64 119.9(5) . . ?
C6 C5 C4 119.6(5) . . ?
C5 C6 C1 122.3(4) . . ?
C5 C6 C7 125.3(4) . . ?
C1 C6 C7 112.4(4) . . ?
N1 C7 N2 108.7(4) . . ?
N1 C7 C6 119.1(4) . . ?
N2 C7 C6 132.2(4) . . ?
C9 C8 N1 108.1(4) . . ?
C8 C9 N2 106.6(5) . . ?
C15 C10 C11 122.9(5) . . ?
C15 C10 N2 118.7(5) . . ?
C11 C10 N2 118.4(5) . . ?
C12 C11 C10 116.8(5) . . ?
C12 C11 C16 121.0(5) . . ?
C10 C11 C16 122.2(4) . . ?
C13 C12 C11 121.4(5) . . ?
C14 C13 C12 120.6(5) . . ?
C13 C14 C15 121.2(6) . . ?
C14 C15 C10 117.1(5) . . ?
C14 C15 C19 121.2(5) . . ?
C10 C15 C19 121.8(5) . . ?
C18 C16 C17 111.0(5) . . ?
C18 C16 C11 111.5(5) . . ?
C17 C16 C11 111.4(5) . . ?
C20 C19 C15 110.7(7) . . ?
C20 C19 C21 111.2(8) . . ?
C15 C19 C21 111.3(6) . . ?
C30 N4 C28 107.4(4) . . ?
C30 N4 C31 126.4(4) . . ?
C28 N4 C31 125.6(4) . . ?
C49 N5 C50 107.9(5) . . ?
C49 N5 Ir1 113.2(3) . . ?
C50 N5 Ir1 138.5(4) . . ?
C51 N6 C49 106.0(5) . . ?
C51 N6 C52 128.1(5) . . ?
C49 N6 C52 125.9(5) . . ?
C23 C22 C27 115.6(5) . . ?
C23 C22 Ir1 128.1(4) . . ?
C27 C22 Ir1 116.3(3) . . ?
C24 C23 C22 122.8(5) . . ?
C23 C24 C25 120.5(5) . . ?
C26 C25 C24 119.7(5) . . ?
C26 C25 C65 119.8(5) . . ?
C24 C25 C65 120.5(5) . . ?
C25 C26 C27 119.4(5) . . ?
C26 C27 C22 122.0(4) . . ?
C26 C27 C28 125.7(5) . . ?
C22 C27 C28 112.3(4) . . ?
N3 C28 N4 109.2(4) . . ?
N3 C28 C27 118.3(4) . . ?
N4 C28 C27 132.3(5) . . ?
C30 C29 N3 108.2(5) . . ?
C29 C30 N4 107.4(5) . . ?
C32 C31 C36 123.3(5) . . ?
C32 C31 N4 118.6(5) . . ?
C36 C31 N4 118.0(5) . . ?
C31 C32 C33 116.7(5) . . ?
C31 C32 C37 122.1(5) . . ?
C33 C32 C37 121.1(6) . . ?
C34 C33 C32 121.1(7) . . ?
C35 C34 C33 120.2(6) . . ?
C34 C35 C36 121.9(6) . . ?
C35 C36 C31 116.7(6) . . ?
C35 C36 C40 120.9(6) . . ?
C31 C36 C40 122.4(6) . . ?
C39 C37 C32 113.2(5) . . ?
C39 C37 C38 111.6(6) . . ?
C32 C37 C38 110.1(5) . . ?
C41 C40 C36 111.5(6) . . ?
C41 C40 C42 110.3(7) . . ?
C36 C40 C42 111.6(7) . . ?
C44 C43 C48 115.9(5) . . ?
C44 C43 Ir1 128.3(4) . . ?
C48 C43 Ir1 115.8(3) . . ?
C45 C44 C43 122.3(5) . . ?
C46 C45 C44 120.2(5) . . ?
C45 C46 C47 120.0(6) . . ?
C45 C46 C66 120.3(6) . . ?
C47 C46 C66 119.6(7) . . ?
C46 C47 C48 119.6(6) . . ?
C47 C48 C43 122.1(5) . . ?
C47 C48 C49 125.7(5) . . ?
C43 C48 C49 112.2(5) . . ?
N5 C49 N6 110.5(5) . . ?
N5 C49 C48 118.9(5) . . ?
N6 C49 C48 130.5(5) . . ?
C51 C50 N5 108.5(5) . . ?
C50 C51 N6 107.1(5) . . ?
C57 C52 C53 124.7(8) . . ?
C57 C52 N6 117.3(7) . . ?
C53 C52 N6 118.0(6) . . ?
C54 C53 C52 117.7(6) . . ?
C54 C53 C58 121.4(6) . . ?
C52 C53 C58 120.9(6) . . ?
C53 C54 C55 119.4(8) . . ?
C54 C55 C56 119.0(9) . . ?
C57 C56 C55 122.1(9) . . ?
C56 C57 C52 117.0(9) . . ?
C56 C57 C61 121.2(10) . . ?
C52 C57 C61 121.7(10) . . ?
C60 C58 C53 113.2(7) . . ?
C60 C58 C59 114.2(8) . . ?
C53 C58 C59 111.8(6) . . ?
C63 C61 C62 119.1(11) . . ?
C63 C61 C57 118.1(12) . . ?
C62 C61 C57 110.4(10) . . ?
N7 C64 C4 179.1(7) . . ?
N8 C65 C25 177.3(9) . . ?
N9 C66 C46 178.1(16) . . ?

_refine_diff_density_max         1.674
_refine_diff_density_min         -1.341
_refine_diff_density_rms         0.129

_shelxl_version_number           2013-4



