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

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

data_ic16618
_database_code_depnum_ccdc_archive 'CCDC 1042891'
_audit_update_record             
;
2015-01-11 deposited with the CCDC.
2015-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H20 F8 Ir N5 O'
_chemical_formula_weight         846.74

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   8.6674(4)
_cell_length_b                   11.9882(5)
_cell_length_c                   28.3475(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.2998(11)
_cell_angle_gamma                90.00
_cell_volume                     2914.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6320
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      20.43

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1640
_exptl_absorpt_coefficient_mu    4.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3880
_exptl_absorpt_correction_T_max  0.7063
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25241
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6691
_reflns_number_gt                4728
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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     
'calc w=1/[σ²(Fo²)+(0.0101P)²+30.7713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6691
_refine_ls_number_parameters     454
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.187
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir 0.40107(3) 0.24736(3) 0.366107(11) 0.02717(10) Uani 1 1 d . . .
N1 N 0.3860(8) 0.4024(6) 0.3342(3) 0.0327(17) Uani 1 1 d . . .
N2 N 0.4588(8) 0.2135(6) 0.2974(2) 0.0272(16) Uani 1 1 d . . .
N3 N 0.5076(8) 0.1265(7) 0.2741(3) 0.0343(17) Uani 1 1 d . . .
N4 N 0.1746(7) 0.1949(6) 0.3464(2) 0.0265(15) Uani 1 1 d . . .
N5 N 0.6320(7) 0.2484(8) 0.3976(2) 0.0328(15) Uani 1 1 d . . .
C1 C 0.3436(9) 0.3426(8) 0.4204(3) 0.030(2) Uani 1 1 d . . .
C2 C 0.3233(9) 0.3139(8) 0.4654(3) 0.031(2) Uani 1 1 d . . .
H2 H 0.3363 0.2382 0.4751 0.037 Uiso 1 1 calc R . .
C3 C 0.2839(11) 0.3929(8) 0.4978(3) 0.037(2) Uani 1 1 d . A .
C4 C 0.2603(12) 0.5049(10) 0.4844(4) 0.050(3) Uani 1 1 d . . .
H4 H 0.2300 0.5576 0.5063 0.060 Uiso 1 1 calc R . .
C5 C 0.2806(13) 0.5372(9) 0.4405(4) 0.049(3) Uani 1 1 d . . .
H5 H 0.2662 0.6131 0.4313 0.059 Uiso 1 1 calc R . .
C6 C 0.3236(9) 0.4574(8) 0.4079(3) 0.031(2) Uani 1 1 d . . .
C7 C 0.3473(10) 0.4895(8) 0.3595(3) 0.037(2) Uani 1 1 d . . .
C8 C 0.3307(11) 0.5972(8) 0.3377(3) 0.038(2) Uani 1 1 d . . .
H8 H 0.3042 0.6603 0.3552 0.046 Uiso 1 1 calc R . .
C9 C 0.3537(11) 0.6070(9) 0.2913(4) 0.046(3) Uani 1 1 d . . .
H9 H 0.3436 0.6781 0.2765 0.056 Uiso 1 1 calc R . .
C10 C 0.3913(11) 0.5164(9) 0.2656(4) 0.043(2) Uani 1 1 d . . .
H10 H 0.4044 0.5239 0.2331 0.052 Uiso 1 1 calc R . .
C11 C 0.4097(10) 0.4139(8) 0.2881(3) 0.034(2) Uani 1 1 d . . .
C12 C 0.4529(10) 0.3093(8) 0.2682(3) 0.032(2) Uani 1 1 d . . .
C13 C 0.5030(11) 0.2789(9) 0.2249(3) 0.046(3) Uani 1 1 d . . .
H13 H 0.5120 0.3250 0.1981 0.055 Uiso 1 1 calc R . .
C14 C 0.5369(10) 0.1640(10) 0.2304(3) 0.042(2) Uani 1 1 d . A .
C15 C 0.2586(14) 0.3600(10) 0.5464(4) 0.048(3) Uani 1 1 d . . .
C16 C 0.6003(13) 0.0871(12) 0.1980(4) 0.058(3) Uani 1 1 d . . .
C17 C 0.4096(10) 0.1062(7) 0.3983(3) 0.0307(19) Uani 1 1 d . . .
C18 C 0.2714(9) 0.0412(8) 0.3945(3) 0.0262(19) Uani 1 1 d . . .
C19 C 0.2836(12) -0.0586(9) 0.4185(3) 0.044(3) Uani 1 1 d . . .
C20 C 0.4206(13) -0.0964(9) 0.4454(3) 0.046(3) Uani 1 1 d . . .
H20 H 0.4248 -0.1664 0.4613 0.056 Uiso 1 1 calc R . .
C21 C 0.5486(12) -0.0294(9) 0.4481(3) 0.043(2) Uani 1 1 d . . .
C22 C 0.5502(11) 0.0748(8) 0.4262(3) 0.035(2) Uani 1 1 d . . .
C23 C 0.1410(10) 0.0937(8) 0.3656(3) 0.033(2) Uani 1 1 d . . .
C24 C -0.0108(10) 0.0508(9) 0.3551(3) 0.038(2) Uani 1 1 d . . .
H24 H -0.0354 -0.0190 0.3681 0.045 Uiso 1 1 calc R . .
C25 C -0.1229(11) 0.1083(9) 0.3264(3) 0.043(3) Uani 1 1 d . . .
H25 H -0.2265 0.0804 0.3205 0.052 Uiso 1 1 calc R . .
C26 C -0.0855(11) 0.2074(9) 0.3059(4) 0.044(3) Uani 1 1 d . . .
H26 H -0.1615 0.2471 0.2849 0.053 Uiso 1 1 calc R . .
C27 C 0.0642(9) 0.2470(9) 0.3166(3) 0.0344(18) Uani 1 1 d . . .
H27 H 0.0905 0.3145 0.3022 0.041 Uiso 1 1 calc R . .
C28 C 0.6737(10) 0.1549(8) 0.4250(3) 0.032(2) Uani 1 1 d . . .
C29 C 0.8252(11) 0.1473(10) 0.4500(3) 0.044(3) Uani 1 1 d . . .
H29 H 0.8542 0.0853 0.4702 0.053 Uiso 1 1 calc R . .
C30 C 0.9310(11) 0.2297(9) 0.4452(4) 0.046(3) Uani 1 1 d . . .
H30 H 1.0346 0.2238 0.4614 0.055 Uiso 1 1 calc R . .
C31 C 0.8882(11) 0.3195(9) 0.4175(4) 0.046(3) Uani 1 1 d . . .
H31 H 0.9614 0.3771 0.4145 0.056 Uiso 1 1 calc R . .
C32 C 0.7348(10) 0.3275(8) 0.3930(3) 0.036(2) Uani 1 1 d . . .
H32 H 0.7054 0.3901 0.3731 0.044 Uiso 1 1 calc R . .
F1 F 0.3874(13) 0.3090(10) 0.5709(3) 0.078(3) Uani 0.691(6) 1 d P A 1
F2 F 0.1470(14) 0.2820(12) 0.5474(4) 0.076(3) Uani 0.691(6) 1 d P A 1
F3 F 0.2329(18) 0.4404(10) 0.5754(4) 0.086(3) Uani 0.691(6) 1 d PU A 1
F4 F 0.5713(18) 0.1385(12) 0.1516(4) 0.106(5) Uani 0.691(6) 1 d P A 1
F5 F 0.5224(15) -0.0016(10) 0.1886(5) 0.075(3) Uani 0.691(6) 1 d P A 1
F6 F 0.7457(12) 0.0743(12) 0.2041(5) 0.084(4) Uani 0.691(6) 1 d PU A 1
F1' F 0.239(4) 0.260(3) 0.5539(8) 0.078(3) Uani 0.309(6) 1 d P A 2
F2' F 0.115(3) 0.407(2) 0.5550(8) 0.076(3) Uani 0.309(6) 1 d P A 2
F3' F 0.345(4) 0.414(3) 0.5790(10) 0.086(3) Uani 0.309(6) 1 d P A 2
F4' F 0.513(5) 0.031(4) 0.1662(10) 0.106(5) Uani 0.309(6) 1 d P A 2
F5' F 0.688(3) -0.007(2) 0.2238(9) 0.075(3) Uani 0.309(6) 1 d P A 2
F6' F 0.712(3) 0.131(3) 0.1759(12) 0.084(4) Uani 0.309(6) 1 d P A 2
F7 F 0.1566(8) -0.1274(5) 0.4163(2) 0.0639(18) Uani 1 1 d . . .
F8 F 0.6825(7) -0.0671(5) 0.4748(2) 0.0534(16) Uani 1 1 d . . .
O1 O 0.4462(13) 0.8910(8) 0.2927(4) 0.099(4) Uani 1 1 d . . .
H1 H 0.4419 0.9609 0.2912 0.148 Uiso 1 1 calc R . .
C33 C 0.5786(17) 0.8592(12) 0.3230(5) 0.082(4) Uani 1 1 d . . .
H33A H 0.6689 0.8619 0.3058 0.123 Uiso 1 1 calc R . .
H33B H 0.5653 0.7830 0.3343 0.123 Uiso 1 1 calc R . .
H33C H 0.5955 0.9100 0.3503 0.123 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir C17 1.919(9) . ?
Ir C1 2.035(9) . ?
Ir N4 2.060(6) . ?
Ir N1 2.063(8) . ?
Ir N5 2.070(6) . ?
Ir N2 2.119(6) . ?
N1 C7 1.338(12) . ?
N1 C11 1.357(11) . ?
N2 N3 1.336(10) . ?
N2 C12 1.413(11) . ?
N3 C14 1.375(12) . ?
N4 C27 1.337(10) . ?
N4 C23 1.377(11) . ?
N5 C32 1.321(12) . ?
N5 C28 1.382(12) . ?
C1 C2 1.359(12) . ?
C1 C6 1.425(13) . ?
C2 C3 1.395(12) . ?
C3 C4 1.403(15) . ?
C3 C15 1.479(13) . ?
C4 C5 1.338(14) . ?
C5 C6 1.416(13) . ?
C6 C7 1.468(13) . ?
C7 C8 1.428(13) . ?
C8 C9 1.364(14) . ?
C9 C10 1.373(15) . ?
C10 C11 1.383(13) . ?
C11 C12 1.446(13) . ?
C12 C13 1.408(12) . ?
C13 C14 1.413(16) . ?
C14 C16 1.464(14) . ?
C15 F1' 1.23(4) . ?
C15 F3' 1.28(3) . ?
C15 F3 1.307(15) . ?
C15 F2 1.349(15) . ?
C15 F1 1.371(15) . ?
C15 F2' 1.42(3) . ?
C16 F6 1.257(15) . ?
C16 F5 1.267(16) . ?
C16 F4' 1.28(4) . ?
C16 F6' 1.33(3) . ?
C16 F4 1.441(17) . ?
C16 F5' 1.50(3) . ?
C17 C22 1.404(12) . ?
C17 C18 1.420(11) . ?
C18 C19 1.372(13) . ?
C18 C23 1.442(12) . ?
C19 F7 1.370(11) . ?
C19 C20 1.391(14) . ?
C20 C21 1.363(14) . ?
C21 F8 1.367(10) . ?
C21 C22 1.396(13) . ?
C22 C28 1.442(13) . ?
C23 C24 1.404(12) . ?
C24 C25 1.361(14) . ?
C25 C26 1.381(15) . ?
C26 C27 1.375(12) . ?
C28 C29 1.403(12) . ?
C29 C30 1.367(14) . ?
C30 C31 1.354(15) . ?
C31 C32 1.411(13) . ?
O1 C33 1.384(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
C17 Ir C1 97.6(4) . . ?
C17 Ir N4 80.2(3) . . ?
C1 Ir N4 92.8(3) . . ?
C17 Ir N1 177.1(3) . . ?
C1 Ir N1 79.6(3) . . ?
N4 Ir N1 99.1(3) . . ?
C17 Ir N5 80.3(3) . . ?
C1 Ir N5 89.9(3) . . ?
N4 Ir N5 160.5(3) . . ?
N1 Ir N5 100.4(3) . . ?
C17 Ir N2 105.7(3) . . ?
C1 Ir N2 156.7(3) . . ?
N4 Ir N2 92.0(3) . . ?
N1 Ir N2 77.1(3) . . ?
N5 Ir N2 93.2(2) . . ?
C7 N1 C11 121.4(8) . . ?
C7 N1 Ir 118.2(6) . . ?
C11 N1 Ir 120.3(6) . . ?
N3 N2 C12 109.4(6) . . ?
N3 N2 Ir 137.5(6) . . ?
C12 N2 Ir 112.9(5) . . ?
N2 N3 C14 107.6(8) . . ?
C27 N4 C23 119.2(8) . . ?
C27 N4 Ir 126.6(6) . . ?
C23 N4 Ir 114.2(5) . . ?
C32 N5 C28 120.8(7) . . ?
C32 N5 Ir 125.9(7) . . ?
C28 N5 Ir 113.3(6) . . ?
C2 C1 C6 116.8(9) . . ?
C2 C1 Ir 130.3(7) . . ?
C6 C1 Ir 112.9(6) . . ?
C1 C2 C3 121.6(9) . . ?
C2 C3 C4 120.7(9) . . ?
C2 C3 C15 121.0(9) . . ?
C4 C3 C15 118.2(9) . . ?
C5 C4 C3 119.8(10) . . ?
C4 C5 C6 119.5(11) . . ?
C5 C6 C1 121.6(9) . . ?
C5 C6 C7 121.2(9) . . ?
C1 C6 C7 117.2(8) . . ?
N1 C7 C8 119.4(9) . . ?
N1 C7 C6 112.2(8) . . ?
C8 C7 C6 128.4(9) . . ?
C9 C8 C7 118.3(9) . . ?
C8 C9 C10 121.5(10) . . ?
C9 C10 C11 118.6(9) . . ?
N1 C11 C10 120.7(9) . . ?
N1 C11 C12 111.8(8) . . ?
C10 C11 C12 127.5(8) . . ?
C13 C12 N2 108.1(8) . . ?
C13 C12 C11 134.0(9) . . ?
N2 C12 C11 117.7(7) . . ?
C12 C13 C14 103.9(9) . . ?
N3 C14 C13 110.9(9) . . ?
N3 C14 C16 119.6(10) . . ?
C13 C14 C16 129.4(10) . . ?
F1' C15 F3' 117(2) . . ?
F1' C15 F3 124.5(16) . . ?
F3' C15 F3 46.1(14) . . ?
F1' C15 F2 37.2(12) . . ?
F3' C15 F2 133.2(16) . . ?
F3 C15 F2 108.1(11) . . ?
F1' C15 F1 66.7(15) . . ?
F3' C15 F1 60.8(15) . . ?
F3 C15 F1 102.1(11) . . ?
F2 C15 F1 102.3(11) . . ?
F1' C15 F2' 102.0(18) . . ?
F3' C15 F2' 96.3(18) . . ?
F3 C15 F2' 50.6(11) . . ?
F2 C15 F2' 67.9(13) . . ?
F1 C15 F2' 139.5(13) . . ?
F1' C15 C3 117.6(14) . . ?
F3' C15 C3 112.8(16) . . ?
F3 C15 C3 116.8(11) . . ?
F2 C15 C3 114.0(9) . . ?
F1 C15 C3 111.8(9) . . ?
F2' C15 C3 107.8(13) . . ?
F6 C16 F5 114.8(13) . . ?
F6 C16 F4' 121(2) . . ?
F5 C16 F4' 33.8(17) . . ?
F6 C16 F6' 48.1(13) . . ?
F5 C16 F6' 129.3(15) . . ?
F4' C16 F6' 106(2) . . ?
F6 C16 F4 102.6(11) . . ?
F5 C16 F4 98.6(11) . . ?
F4' C16 F4 64.9(18) . . ?
F6' C16 F4 56.4(14) . . ?
F6 C16 C14 116.8(10) . . ?
F5 C16 C14 115.0(10) . . ?
F4' C16 C14 123(2) . . ?
F6' C16 C14 114.1(16) . . ?
F4 C16 C14 105.8(11) . . ?
F6 C16 F5' 54.0(11) . . ?
F5 C16 F5' 71.6(13) . . ?
F4' C16 F5' 99(2) . . ?
F6' C16 F5' 100.3(18) . . ?
F4 C16 F5' 141.3(13) . . ?
C14 C16 F5' 112.3(12) . . ?
C22 C17 C18 123.3(8) . . ?
C22 C17 Ir 118.4(7) . . ?
C18 C17 Ir 118.3(6) . . ?
C19 C18 C17 115.9(8) . . ?
C19 C18 C23 131.3(8) . . ?
C17 C18 C23 112.8(8) . . ?
F7 C19 C18 119.9(9) . . ?
F7 C19 C20 116.4(9) . . ?
C18 C19 C20 123.7(9) . . ?
C21 C20 C19 117.5(10) . . ?
C20 C21 F8 117.1(9) . . ?
C20 C21 C22 124.2(9) . . ?
F8 C21 C22 118.7(9) . . ?
C21 C22 C17 115.3(9) . . ?
C21 C22 C28 131.4(9) . . ?
C17 C22 C28 113.2(8) . . ?
N4 C23 C24 119.0(8) . . ?
N4 C23 C18 114.5(8) . . ?
C24 C23 C18 126.4(9) . . ?
C25 C24 C23 120.5(10) . . ?
C24 C25 C26 119.8(9) . . ?
C27 C26 C25 118.4(9) . . ?
N4 C27 C26 123.0(10) . . ?
N5 C28 C29 119.2(9) . . ?
N5 C28 C22 114.7(7) . . ?
C29 C28 C22 126.1(9) . . ?
C30 C29 C28 119.6(10) . . ?
C31 C30 C29 120.1(9) . . ?
C30 C31 C32 120.0(10) . . ?
N5 C32 C31 120.2(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.504
_refine_diff_density_min         -1.497
_refine_diff_density_rms         0.151
####################################################################### 
# 
# 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_ic16926
_database_code_depnum_ccdc_archive 'CCDC 1042892'
_audit_update_record             
;
2015-01-11 deposited with the CCDC.
2015-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45.50 H31.50 Cl4.50 F6 Ir N5'
_chemical_formula_weight         1113.98

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'
F F 0.0171 0.0103 '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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   18.5300(3)
_cell_length_b                   12.8977(2)
_cell_length_c                   20.1368(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.7780(9)
_cell_angle_gamma                90.00
_cell_volume                     4437.26(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    21667
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2188
_exptl_absorpt_coefficient_mu    3.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6339
_exptl_absorpt_correction_T_max  0.7757
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21667
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7806
_reflns_number_gt                5660
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'NONIUS COLLECT'
_computing_cell_refinement       DENZO-SMN
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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     
'calc w=1/[σ²(Fo²)+(0.0783P)²+0.2295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7806
_refine_ls_number_parameters     567
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1353
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir -0.046110(14) 0.11721(2) 0.235452(14) 0.02889(12) Uani 1 1 d . . .
N1 N -0.1053(3) 0.2560(5) 0.2271(3) 0.0330(14) Uani 1 1 d . . .
N2 N -0.1626(3) 0.0776(5) 0.1695(3) 0.0313(14) Uani 1 1 d . . .
N3 N -0.2014(3) -0.0084(5) 0.1398(3) 0.0353(15) Uani 1 1 d . . .
N4 N -0.0104(3) 0.1341(5) 0.1524(3) 0.0316(14) Uani 1 1 d . . .
N5 N -0.0595(3) 0.0516(5) 0.3225(3) 0.0308(14) Uani 1 1 d . . .
C1 C 0.0415(4) 0.2103(6) 0.2996(4) 0.0320(17) Uani 1 1 d . . .
C2 C 0.1193(4) 0.1835(6) 0.3404(4) 0.0339(18) Uani 1 1 d . . .
H2 H 0.1366 0.1147 0.3381 0.041 Uiso 1 1 calc R . .
C3 C 0.1722(4) 0.2566(7) 0.3845(4) 0.0410(19) Uani 1 1 d . . .
C4 C 0.1493(5) 0.3577(7) 0.3875(5) 0.049(2) Uani 1 1 d . . .
H4 H 0.1855 0.4071 0.4170 0.059 Uiso 1 1 calc R . .
C5 C 0.0725(5) 0.3863(6) 0.3469(5) 0.045(2) Uani 1 1 d . . .
H5 H 0.0568 0.4561 0.3484 0.054 Uiso 1 1 calc R . .
C6 C 0.0181(4) 0.3150(6) 0.3039(4) 0.0364(18) Uani 1 1 d . . .
C7 C -0.0638(4) 0.3394(6) 0.2618(4) 0.0375(18) Uani 1 1 d . . .
C8 C -0.1025(5) 0.4329(7) 0.2563(5) 0.052(2) Uani 1 1 d . . .
H8 H -0.0749 0.4923 0.2813 0.062 Uiso 1 1 calc R . .
C9 C -0.1817(5) 0.4390(7) 0.2140(5) 0.055(2) Uani 1 1 d . . .
H9 H -0.2082 0.5033 0.2097 0.066 Uiso 1 1 calc R . .
C10 C -0.2230(5) 0.3527(7) 0.1779(5) 0.048(2) Uani 1 1 d . . .
H10 H -0.2773 0.3567 0.1488 0.057 Uiso 1 1 calc R . .
C11 C -0.1825(4) 0.2605(6) 0.1859(4) 0.0346(18) Uani 1 1 d . . .
C12 C -0.2141(4) 0.1601(6) 0.1556(4) 0.0351(18) Uani 1 1 d . . .
C13 C -0.2893(4) 0.1231(6) 0.1151(4) 0.0386(19) Uani 1 1 d . . .
H13 H -0.3372 0.1604 0.0977 0.046 Uiso 1 1 calc R . .
C14 C -0.2771(4) 0.0201(6) 0.1069(4) 0.0388(19) Uani 1 1 d . . .
C15 C 0.2530(5) 0.2218(7) 0.4304(5) 0.052(2) Uani 1 1 d . . .
C16 C -0.3374(5) -0.0614(8) 0.0686(5) 0.056(2) Uani 1 1 d . . .
C17 C 0.0211(4) -0.0018(6) 0.2498(4) 0.0280(16) Uani 1 1 d . . .
C18 C 0.0672(4) -0.0104(6) 0.2083(4) 0.0317(17) Uani 1 1 d . . .
C19 C 0.1316(4) -0.0772(6) 0.2334(4) 0.0374(18) Uani 1 1 d . . .
H19 H 0.1646 -0.0826 0.2074 0.045 Uiso 1 1 calc R . .
C20 C 0.1485(5) -0.1366(6) 0.2961(4) 0.045(2) Uani 1 1 d . A .
C21 C 0.1012(4) -0.1264(6) 0.3352(4) 0.0366(18) Uani 1 1 d . . .
H21 H 0.1135 -0.1630 0.3792 0.044 Uiso 1 1 calc R . .
C22 C 0.0362(4) -0.0627(5) 0.3096(4) 0.0328(17) Uani 1 1 d . . .
C23 C 0.0427(4) 0.0632(5) 0.1489(4) 0.0303(16) Uani 1 1 d . . .
C24 C 0.0666(4) 0.0691(6) 0.0883(4) 0.0315(17) Uani 1 1 d . . .
C25 C 0.1133(4) -0.0085(6) 0.0740(4) 0.0358(18) Uani 1 1 d . . .
H25 H 0.1304 -0.0665 0.1053 0.043 Uiso 1 1 calc R . .
C26 C 0.1342(4) -0.0011(6) 0.0159(4) 0.0401(19) Uani 1 1 d . . .
H26 H 0.1660 -0.0533 0.0079 0.048 Uiso 1 1 calc R . .
C27 C 0.1093(5) 0.0816(6) -0.0311(4) 0.044(2) Uani 1 1 d . . .
H27 H 0.1241 0.0859 -0.0712 0.053 Uiso 1 1 calc R . .
C28 C 0.0628(4) 0.1584(7) -0.0200(4) 0.0413(19) Uani 1 1 d . . .
H28 H 0.0464 0.2156 -0.0521 0.050 Uiso 1 1 calc R . .
C29 C 0.0402(4) 0.1516(6) 0.0384(4) 0.0343(17) Uani 1 1 d . . .
C30 C -0.0131(4) 0.2225(6) 0.0475(4) 0.0397(19) Uani 1 1 d . . .
H30 H -0.0326 0.2780 0.0144 0.048 Uiso 1 1 calc R . .
C31 C -0.0367(4) 0.2125(6) 0.1024(4) 0.0357(18) Uani 1 1 d . . .
H31 H -0.0730 0.2614 0.1068 0.043 Uiso 1 1 calc R . .
C32 C -0.0183(4) -0.0372(6) 0.3484(4) 0.0304(16) Uani 1 1 d . . .
C33 C -0.0316(4) -0.0966(5) 0.4020(4) 0.0314(17) Uani 1 1 d . . .
C34 C -0.0017(4) -0.1976(6) 0.4219(4) 0.0370(18) Uani 1 1 d . . .
H34 H 0.0270 -0.2298 0.3973 0.044 Uiso 1 1 calc R . .
C35 C -0.0135(4) -0.2497(6) 0.4757(4) 0.0418(19) Uani 1 1 d . . .
H35 H 0.0064 -0.3179 0.4881 0.050 Uiso 1 1 calc R . .
C36 C -0.0553(4) -0.2021(7) 0.5131(4) 0.042(2) Uani 1 1 d . . .
H36 H -0.0602 -0.2366 0.5528 0.051 Uiso 1 1 calc R . .
C37 C -0.0885(4) -0.1077(6) 0.4927(4) 0.0386(19) Uani 1 1 d . . .
H37 H -0.1187 -0.0782 0.5168 0.046 Uiso 1 1 calc R . .
C38 C -0.0787(4) -0.0525(6) 0.4362(4) 0.0333(17) Uani 1 1 d . . .
C39 C -0.1157(4) 0.0415(6) 0.4113(4) 0.0349(18) Uani 1 1 d . . .
H39 H -0.1468 0.0724 0.4340 0.042 Uiso 1 1 calc R . .
C40 C -0.1074(4) 0.0894(6) 0.3544(4) 0.0334(17) Uani 1 1 d . . .
H40 H -0.1359 0.1513 0.3362 0.040 Uiso 1 1 calc R . .
C41 C 0.2225(5) -0.2050(7) 0.3270(5) 0.063(3) Uani 1 1 d D . .
C42 C 0.2689(9) -0.2122(13) 0.2785(8) 0.072(4) Uani 0.736(12) 1 d PDU A 1
H42A H 0.2363 -0.2444 0.2326 0.108 Uiso 0.736(12) 1 calc PR A 1
H42B H 0.3159 -0.2542 0.3023 0.108 Uiso 0.736(12) 1 calc PR A 1
H42C H 0.2841 -0.1424 0.2696 0.108 Uiso 0.736(12) 1 calc PR A 1
C43 C 0.2753(8) -0.1562(13) 0.4003(7) 0.082(4) Uani 0.736(12) 1 d PDU A 1
H43A H 0.2805 -0.0816 0.3941 0.123 Uiso 0.736(12) 1 calc PR A 1
H43B H 0.3271 -0.1887 0.4175 0.123 Uiso 0.736(12) 1 calc PR A 1
H43C H 0.2516 -0.1676 0.4355 0.123 Uiso 0.736(12) 1 calc PR A 1
C44 C 0.2022(9) -0.3140(9) 0.3448(10) 0.085(5) Uani 0.736(12) 1 d PDU A 1
H44A H 0.1626 -0.3450 0.3016 0.128 Uiso 0.736(12) 1 calc PR A 1
H44B H 0.1815 -0.3095 0.3827 0.128 Uiso 0.736(12) 1 calc PR A 1
H44C H 0.2493 -0.3572 0.3614 0.128 Uiso 0.736(12) 1 calc PR A 1
C42' C 0.286(2) -0.163(4) 0.301(3) 0.072(4) Uani 0.264(12) 1 d PD A 2
H42D H 0.2718 -0.1827 0.2507 0.108 Uiso 0.264(12) 1 calc PR A 2
H42E H 0.3365 -0.1935 0.3308 0.108 Uiso 0.264(12) 1 calc PR A 2
H42F H 0.2884 -0.0878 0.3058 0.108 Uiso 0.264(12) 1 calc PR A 2
C43' C 0.245(2) -0.249(4) 0.4031(13) 0.082(4) Uani 0.264(12) 1 d PD A 2
H43D H 0.2179 -0.3149 0.4006 0.123 Uiso 0.264(12) 1 calc PR A 2
H43E H 0.2309 -0.1998 0.4328 0.123 Uiso 0.264(12) 1 calc PR A 2
H43F H 0.3020 -0.2611 0.4245 0.123 Uiso 0.264(12) 1 calc PR A 2
C44' C 0.197(2) -0.3141(18) 0.294(2) 0.085(5) Uani 0.264(12) 1 d PD A 2
H44D H 0.1645 -0.3072 0.2424 0.128 Uiso 0.264(12) 1 calc PR A 2
H44E H 0.1676 -0.3490 0.3183 0.128 Uiso 0.264(12) 1 calc PR A 2
H44F H 0.2439 -0.3551 0.2995 0.128 Uiso 0.264(12) 1 calc PR A 2
F1 F 0.2637(3) 0.1215(4) 0.4335(4) 0.094(2) Uani 1 1 d . . .
F2 F 0.3070(3) 0.2641(5) 0.4107(3) 0.0792(17) Uani 1 1 d . . .
F3 F 0.2745(3) 0.2546(5) 0.4993(3) 0.0850(19) Uani 1 1 d . . .
F4 F -0.4103(3) -0.0234(5) 0.0508(4) 0.108(3) Uani 1 1 d . . .
F5 F -0.3351(3) -0.1448(4) 0.1062(3) 0.0748(16) Uani 1 1 d . . .
F6 F -0.3323(4) -0.0917(5) 0.0074(3) 0.0863(19) Uani 1 1 d . . .
C45 C 0.6379(5) 0.2527(7) 0.3232(5) 0.055(2) Uani 1 1 d . . .
H45 H 0.6454 0.3290 0.3318 0.066 Uiso 1 1 calc R . .
Cl1 Cl 0.69375(15) 0.1880(2) 0.40317(13) 0.0693(7) Uani 1 1 d . . .
Cl2 Cl 0.67023(17) 0.2184(2) 0.25422(14) 0.0736(7) Uani 1 1 d . . .
Cl3 Cl 0.53912(14) 0.2245(2) 0.29748(14) 0.0706(7) Uani 1 1 d . . .
C46 C 0.4607(7) -0.0106(11) 0.3922(7) 0.102(8) Uiso 0.50 1 d PD B 1
H46 H 0.4388 -0.0625 0.4163 0.122 Uiso 0.50 1 calc PR B 1
Cl4 Cl 0.4093(5) 0.1043(7) 0.3793(6) 0.167(4) Uiso 0.50 1 d PD B 1
Cl5 Cl 0.5594(5) 0.0075(8) 0.4421(5) 0.165(4) Uiso 0.50 1 d PD B 1
Cl6 Cl 0.4480(7) -0.0542(10) 0.3053(6) 0.239(6) Uiso 0.50 1 d PD B 1


_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
Ir C17 1.926(7) . ?
Ir C1 2.030(7) . ?
Ir N4 2.034(6) . ?
Ir N5 2.046(6) . ?
Ir N1 2.072(6) . ?
Ir N2 2.113(6) . ?
N1 C11 1.349(8) . ?
N1 C7 1.349(9) . ?
N2 N3 1.332(8) . ?
N2 C12 1.384(9) . ?
N3 C14 1.350(9) . ?
N4 C23 1.366(9) . ?
N4 C31 1.377(9) . ?
N5 C32 1.364(9) . ?
N5 C40 1.371(9) . ?
C1 C2 1.399(10) . ?
C1 C6 1.431(10) . ?
C2 C3 1.402(10) . ?
C3 C4 1.380(11) . ?
C3 C15 1.492(11) . ?
C4 C5 1.389(11) . ?
C5 C6 1.390(11) . ?
C6 C7 1.458(10) . ?
C7 C8 1.385(11) . ?
C8 C9 1.386(11) . ?
C9 C10 1.387(12) . ?
C10 C11 1.382(11) . ?
C11 C12 1.455(11) . ?
C12 C13 1.397(10) . ?
C13 C14 1.369(10) . ?
C14 C16 1.510(11) . ?
C15 F1 1.306(10) . ?
C15 F2 1.330(9) . ?
C15 F3 1.353(10) . ?
C16 F5 1.306(11) . ?
C16 F6 1.331(11) . ?
C16 F4 1.348(9) . ?
C17 C22 1.373(10) . ?
C17 C18 1.411(9) . ?
C18 C19 1.399(10) . ?
C18 C23 1.456(10) . ?
C19 C20 1.404(11) . ?
C20 C21 1.394(11) . ?
C20 C41 1.544(11) . ?
C21 C22 1.381(10) . ?
C22 C32 1.531(10) . ?
C23 C24 1.453(10) . ?
C24 C29 1.414(11) . ?
C24 C25 1.424(10) . ?
C25 C26 1.369(10) . ?
C26 C27 1.382(11) . ?
C27 C28 1.386(11) . ?
C28 C29 1.396(10) . ?
C29 C30 1.409(10) . ?
C30 C31 1.344(10) . ?
C32 C33 1.422(10) . ?
C33 C34 1.412(10) . ?
C33 C38 1.423(10) . ?
C34 C35 1.363(10) . ?
C35 C36 1.413(11) . ?
C36 C37 1.354(10) . ?
C37 C38 1.412(10) . ?
C38 C39 1.387(10) . ?
C39 C40 1.362(10) . ?
C41 C43' 1.533(10) . ?
C41 C42 1.533(9) . ?
C41 C44 1.533(9) . ?
C41 C42' 1.546(10) . ?
C41 C44' 1.551(10) . ?
C41 C43 1.554(9) . ?
C45 Cl3 1.737(9) . ?
C45 Cl1 1.752(9) . ?
C45 Cl2 1.768(9) . ?
C46 Cl4 1.726(10) . ?
C46 Cl5 1.728(10) . ?
C46 Cl6 1.765(10) . ?

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
C17 Ir C1 93.7(3) . . ?
C17 Ir N4 79.1(3) . . ?
C1 Ir N4 91.5(2) . . ?
C17 Ir N5 80.1(3) . . ?
C1 Ir N5 91.8(2) . . ?
N4 Ir N5 159.1(2) . . ?
C17 Ir N1 172.6(3) . . ?
C1 Ir N1 79.0(3) . . ?
N4 Ir N1 99.8(2) . . ?
N5 Ir N1 101.0(2) . . ?
C17 Ir N2 110.2(3) . . ?
C1 Ir N2 156.0(3) . . ?
N4 Ir N2 95.0(2) . . ?
N5 Ir N2 90.3(2) . . ?
N1 Ir N2 77.2(2) . . ?
C11 N1 C7 122.7(6) . . ?
C11 N1 Ir 119.3(5) . . ?
C7 N1 Ir 118.0(5) . . ?
N3 N2 C12 109.9(6) . . ?
N3 N2 Ir 136.6(5) . . ?
C12 N2 Ir 113.5(5) . . ?
N2 N3 C14 105.7(6) . . ?
C23 N4 C31 120.8(6) . . ?
C23 N4 Ir 116.2(5) . . ?
C31 N4 Ir 123.0(5) . . ?
C32 N5 C40 119.2(6) . . ?
C32 N5 Ir 116.0(4) . . ?
C40 N5 Ir 124.8(5) . . ?
C2 C1 C6 117.7(7) . . ?
C2 C1 Ir 128.0(6) . . ?
C6 C1 Ir 114.2(5) . . ?
C1 C2 C3 120.9(7) . . ?
C4 C3 C2 120.8(7) . . ?
C4 C3 C15 120.6(7) . . ?
C2 C3 C15 118.5(8) . . ?
C3 C4 C5 119.2(8) . . ?
C4 C5 C6 121.4(8) . . ?
C5 C6 C1 119.9(7) . . ?
C5 C6 C7 124.0(7) . . ?
C1 C6 C7 116.1(6) . . ?
N1 C7 C8 118.6(7) . . ?
N1 C7 C6 112.7(6) . . ?
C8 C7 C6 128.6(7) . . ?
C7 C8 C9 119.4(8) . . ?
C8 C9 C10 121.0(8) . . ?
C11 C10 C9 117.7(7) . . ?
N1 C11 C10 120.5(7) . . ?
N1 C11 C12 112.3(6) . . ?
C10 C11 C12 127.2(7) . . ?
N2 C12 C13 108.0(7) . . ?
N2 C12 C11 117.7(6) . . ?
C13 C12 C11 134.2(7) . . ?
C14 C13 C12 103.2(6) . . ?
N3 C14 C13 113.2(7) . . ?
N3 C14 C16 118.9(7) . . ?
C13 C14 C16 127.9(7) . . ?
F1 C15 F2 107.5(8) . . ?
F1 C15 F3 106.5(8) . . ?
F2 C15 F3 102.8(7) . . ?
F1 C15 C3 115.2(7) . . ?
F2 C15 C3 112.4(7) . . ?
F3 C15 C3 111.6(7) . . ?
F5 C16 F6 107.3(8) . . ?
F5 C16 F4 105.0(8) . . ?
F6 C16 F4 106.5(8) . . ?
F5 C16 C14 115.2(8) . . ?
F6 C16 C14 111.9(8) . . ?
F4 C16 C14 110.5(7) . . ?
C22 C17 C18 120.6(6) . . ?
C22 C17 Ir 119.2(5) . . ?
C18 C17 Ir 118.6(5) . . ?
C19 C18 C17 117.5(6) . . ?
C19 C18 C23 130.5(6) . . ?
C17 C18 C23 111.6(6) . . ?
C18 C19 C20 121.6(7) . . ?
C21 C20 C19 119.1(7) . . ?
C21 C20 C41 118.8(7) . . ?
C19 C20 C41 121.9(7) . . ?
C22 C21 C20 119.6(7) . . ?
C17 C22 C21 121.3(7) . . ?
C17 C22 C32 111.9(6) . . ?
C21 C22 C32 126.1(7) . . ?
N4 C23 C24 118.0(6) . . ?
N4 C23 C18 113.2(6) . . ?
C24 C23 C18 128.8(6) . . ?
C29 C24 C25 117.1(6) . . ?
C29 C24 C23 120.2(6) . . ?
C25 C24 C23 122.6(7) . . ?
C26 C25 C24 121.2(7) . . ?
C25 C26 C27 120.6(7) . . ?
C26 C27 C28 120.3(7) . . ?
C27 C28 C29 119.9(8) . . ?
C28 C29 C30 121.5(7) . . ?
C28 C29 C24 120.8(7) . . ?
C30 C29 C24 117.6(6) . . ?
C31 C30 C29 120.9(7) . . ?
C30 C31 N4 122.4(7) . . ?
N5 C32 C33 120.4(6) . . ?
N5 C32 C22 111.6(6) . . ?
C33 C32 C22 127.9(6) . . ?
C34 C33 C32 123.2(7) . . ?
C34 C33 C38 118.6(7) . . ?
C32 C33 C38 118.2(7) . . ?
C35 C34 C33 120.9(7) . . ?
C34 C35 C36 120.0(8) . . ?
C37 C36 C35 120.5(8) . . ?
C36 C37 C38 120.8(7) . . ?
C39 C38 C37 122.1(7) . . ?
C39 C38 C33 118.9(7) . . ?
C37 C38 C33 118.9(7) . . ?
C40 C39 C38 120.0(7) . . ?
C39 C40 N5 122.6(7) . . ?
C43' C41 C42 127.4(16) . . ?
C43' C41 C44 54.8(19) . . ?
C42 C41 C44 110.1(10) . . ?
C43' C41 C20 118.3(15) . . ?
C42 C41 C20 114.0(8) . . ?
C44 C41 C20 111.0(8) . . ?
C43' C41 C42' 121(2) . . ?
C42 C41 C42' 28.9(18) . . ?
C44 C41 C42' 133.0(19) . . ?
C20 C41 C42' 109.6(18) . . ?
C43' C41 C44' 91(2) . . ?
C42 C41 C44' 79.6(17) . . ?
C44 C41 C44' 37.7(17) . . ?
C20 C41 C44' 105.8(17) . . ?
C42' C41 C44' 108(2) . . ?
C43' C41 C43 51.1(19) . . ?
C42 C41 C43 109.1(10) . . ?
C44 C41 C43 105.7(11) . . ?
C20 C41 C43 106.6(8) . . ?
C42' C41 C43 84(2) . . ?
C44' C41 C43 139(2) . . ?
Cl3 C45 Cl1 110.7(5) . . ?
Cl3 C45 Cl2 110.6(5) . . ?
Cl1 C45 Cl2 110.1(5) . . ?
Cl4 C46 Cl5 111.7(8) . . ?
Cl4 C46 Cl6 105.7(7) . . ?
Cl5 C46 Cl6 108.9(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.130
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.182

