# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1049931'
_audit_update_record             
;
2015-02-16 deposited with the CCDC.
2015-05-08 downloaded from the CCDC.
;

_audit_creation_date             2015-02-04T12:24:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C54 H74 Ir2 N4, 2(B F4), 2(C H2 Cl2)'
_chemical_formula_sum            'C56 H78 B2 Cl4 F8 Ir2 N4'
_chemical_formula_weight         1507.04

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.338(2)
_cell_length_b                   16.601(2)
_cell_length_c                   18.949(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.101(2)
_cell_angle_gamma                90
_cell_volume                     6059.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.31

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

_exptl_crystal_description       prisms
_exptl_crystal_colour            red-brown
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2984
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    4.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.215
_exptl_absorpt_correction_T_max  0.317

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_number            27196
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.927
_reflns_number_total             7154
_reflns_number_gt                5661
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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. Distance between the residual
 density pick Q1 and Ir1 is 0.84 A.
;
_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)+(0.0499P)²+91.9966P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7154
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.106
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         7.365
_refine_diff_density_min         -1.539
_refine_diff_density_rms         0.187

#----------------------------------------------------------------------------#
#                   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 0 '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'
B B 0.0013 0.0007 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.244734(12) 0.170564(14) 0.502844(12) 0.01713(8) Uani 1 1 d . . .
H1 H 0.165(5) 0.213(6) 0.487(5) 0.06(3) Uiso 1 1 d . . .
N11 N 0.2189(3) 0.2400(3) 0.3559(3) 0.0195(11) Uani 1 1 d . . .
C12 C 0.2327(3) 0.1735(4) 0.3957(3) 0.0159(11) Uani 1 1 d . . .
N13 N 0.2291(3) 0.1124(3) 0.3469(3) 0.0187(11) Uani 1 1 d . . .
C14 C 0.2135(4) 0.1422(4) 0.2787(3) 0.0240(14) Uani 1 1 d . . .
H14 H 0.2083 0.1116 0.2362 0.029 Uiso 1 1 calc R . .
C15 C 0.2070(4) 0.2228(4) 0.2842(3) 0.0240(14) Uani 1 1 d . . .
H15 H 0.1964 0.26 0.2468 0.029 Uiso 1 1 calc R . .
C21 C 0.2168(3) 0.3188(4) 0.3874(3) 0.0189(12) Uani 1 1 d . . .
C22 C 0.2777(3) 0.3675(4) 0.3903(3) 0.0181(12) Uani 1 1 d . . .
C23 C 0.2765(3) 0.4396(4) 0.4298(3) 0.0228(14) Uani 1 1 d . . .
H23 H 0.3151 0.4753 0.4315 0.027 Uiso 1 1 calc R . .
C24 C 0.2188(3) 0.4588(4) 0.4664(3) 0.0225(13) Uani 1 1 d . . .
H24 H 0.2209 0.5043 0.4969 0.027 Uiso 1 1 calc R . .
C25 C 0.1577(3) 0.4118(4) 0.4588(4) 0.0231(14) Uani 1 1 d . . .
H25 H 0.1186 0.4277 0.4825 0.028 Uiso 1 1 calc R . .
C26 C 0.1538(3) 0.3423(4) 0.4170(3) 0.0211(13) Uani 1 1 d . . .
C31 C 0.2353(3) 0.0275(4) 0.3636(3) 0.0199(13) Uani 1 1 d . . .
C32 C 0.2989(3) -0.0101(4) 0.3562(3) 0.0235(14) Uani 1 1 d . . .
C33 C 0.3038(4) -0.0905(4) 0.3766(4) 0.0308(16) Uani 1 1 d . . .
H33 H 0.3456 -0.1191 0.3714 0.037 Uiso 1 1 calc R . .
C34 C 0.2493(4) -0.1295(4) 0.4043(4) 0.0320(16) Uani 1 1 d . . .
H34 H 0.2548 -0.1835 0.4204 0.038 Uiso 1 1 calc R . .
C35 C 0.1865(4) -0.0903(4) 0.4087(4) 0.0290(16) Uani 1 1 d . . .
H35 H 0.1488 -0.1184 0.4264 0.035 Uiso 1 1 calc R . .
C36 C 0.1780(3) -0.0109(4) 0.3878(3) 0.0217(13) Uani 1 1 d . . .
C221 C 0.3394(3) 0.3458(4) 0.3496(3) 0.0247(14) Uani 1 1 d . . .
H221 H 0.3388 0.2863 0.341 0.03 Uiso 1 1 calc R . .
C222 C 0.4090(4) 0.3682(5) 0.3883(4) 0.0373(18) Uani 1 1 d . . .
H222 H 0.4103 0.3504 0.4377 0.056 Uiso 1 1 calc R . .
H223 H 0.4151 0.4268 0.3868 0.056 Uiso 1 1 calc R . .
H224 H 0.4465 0.342 0.3652 0.056 Uiso 1 1 calc R . .
C223 C 0.3298(4) 0.3889(5) 0.2778(4) 0.0397(19) Uani 1 1 d . . .
H225 H 0.2846 0.3744 0.2536 0.06 Uiso 1 1 calc R . .
H226 H 0.3668 0.3726 0.2487 0.06 Uiso 1 1 calc R . .
H227 H 0.3319 0.4473 0.2853 0.06 Uiso 1 1 calc R . .
C261 C 0.0875(3) 0.2936(4) 0.4047(4) 0.0254(14) Uani 1 1 d . . .
H261 H 0.1005 0.2354 0.4032 0.031 Uiso 1 1 calc R . .
C262 C 0.0390(4) 0.3042(5) 0.4630(5) 0.0383(19) Uani 1 1 d . . .
H262 H 0.0645 0.2941 0.5091 0.057 Uiso 1 1 calc R . .
H263 H 0.0003 0.2661 0.4556 0.057 Uiso 1 1 calc R . .
H264 H 0.0208 0.3594 0.4617 0.057 Uiso 1 1 calc R . .
C263 C 0.0507(4) 0.3157(5) 0.3328(4) 0.0383(19) Uani 1 1 d . . .
H265 H 0.0797 0.3002 0.2953 0.058 Uiso 1 1 calc R . .
H266 H 0.0424 0.374 0.3309 0.058 Uiso 1 1 calc R . .
H267 H 0.0062 0.2872 0.3262 0.058 Uiso 1 1 calc R . .
C321 C 0.3579(4) 0.0317(5) 0.3230(4) 0.0317(17) Uani 1 1 d . . .
H321 H 0.3492 0.091 0.3239 0.038 Uiso 1 1 calc R . .
C322 C 0.3589(5) 0.0060(7) 0.2458(5) 0.059(3) Uani 1 1 d . . .
H322 H 0.3144 0.0196 0.2197 0.088 Uiso 1 1 calc R . .
H323 H 0.3665 -0.0522 0.2435 0.088 Uiso 1 1 calc R . .
H324 H 0.3965 0.0342 0.2246 0.088 Uiso 1 1 calc R . .
C323 C 0.4281(4) 0.0158(7) 0.3622(5) 0.057(3) Uani 1 1 d . . .
H325 H 0.4264 0.0285 0.4126 0.085 Uiso 1 1 calc R . .
H326 H 0.4631 0.0498 0.3425 0.085 Uiso 1 1 calc R . .
H327 H 0.4405 -0.041 0.357 0.085 Uiso 1 1 calc R . .
C361 C 0.1087(3) 0.0325(4) 0.3897(4) 0.0261(15) Uani 1 1 d . . .
H361 H 0.1191 0.0897 0.4034 0.031 Uiso 1 1 calc R . .
C362 C 0.0630(4) -0.0022(6) 0.4440(4) 0.039(2) Uani 1 1 d . . .
H362 H 0.0901 -0.0066 0.4901 0.059 Uiso 1 1 calc R . .
H363 H 0.0464 -0.0556 0.4285 0.059 Uiso 1 1 calc R . .
H364 H 0.0232 0.0335 0.4483 0.059 Uiso 1 1 calc R . .
C363 C 0.0670(4) 0.0339(5) 0.3175(4) 0.0360(18) Uani 1 1 d . . .
H365 H 0.0956 0.0561 0.2821 0.054 Uiso 1 1 calc R . .
H366 H 0.0256 0.0674 0.32 0.054 Uiso 1 1 calc R . .
H367 H 0.0529 -0.0211 0.304 0.054 Uiso 1 1 calc R . .
B1 B 0.1376(5) 0.1653(6) 0.1001(5) 0.0333(18) Uani 1 1 d . . .
F11 F 0.1174(3) 0.2235(3) 0.1456(3) 0.0493(13) Uani 1 1 d . . .
F12 F 0.1080(4) 0.1806(4) 0.0333(3) 0.073(2) Uani 1 1 d . . .
F13 F 0.1195(3) 0.0898(3) 0.1224(3) 0.0587(15) Uani 1 1 d . . .
F14 F 0.2084(3) 0.1668(4) 0.1017(5) 0.088(2) Uani 1 1 d . . .
Cl11 Cl 0.40700(11) 0.10419(14) 0.06477(13) 0.0463(5) Uani 1 1 d . . .
Cl12 Cl 0.4213(2) 0.2223(2) 0.1770(2) 0.0983(12) Uani 1 1 d . . .
C1 C 0.3743(5) 0.1938(6) 0.0969(6) 0.055(3) Uani 1 1 d . . .
H11 H 0.3247 0.1865 0.1048 0.066 Uiso 1 1 calc R . .
H12 H 0.3774 0.237 0.0613 0.066 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   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 C12 2.024(6) . ?
Ir1 C21 2.153(6) 7_556 ?
Ir1 C22 2.200(6) 7_556 ?
Ir1 C23 2.289(6) 7_556 ?
Ir1 C24 2.318(7) 7_556 ?
Ir1 C26 2.381(6) 7_556 ?
Ir1 C25 2.391(6) 7_556 ?
Ir1 Ir1 2.6482(6) 7_556 ?
Ir1 H1 1.70(9) . ?
N11 C12 1.350(8) . ?
N11 C15 1.387(8) . ?
N11 C21 1.439(8) . ?
C12 N13 1.370(8) . ?
N13 C14 1.392(8) . ?
N13 C31 1.447(8) . ?
C14 C15 1.348(10) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C21 C22 1.425(9) . ?
C21 C26 1.440(9) . ?
C21 Ir1 2.153(6) 7_556 ?
C22 C23 1.412(9) . ?
C22 C221 1.523(8) . ?
C22 Ir1 2.200(6) 7_556 ?
C23 C24 1.402(9) . ?
C23 Ir1 2.289(6) 7_556 ?
C23 H23 0.95 . ?
C24 C25 1.414(9) . ?
C24 Ir1 2.318(6) 7_556 ?
C24 H24 0.95 . ?
C25 C26 1.399(9) . ?
C25 Ir1 2.391(6) 7_556 ?
C25 H25 0.95 . ?
C26 C261 1.517(9) . ?
C26 Ir1 2.381(6) 7_556 ?
C31 C36 1.391(9) . ?
C31 C32 1.398(9) . ?
C32 C33 1.390(10) . ?
C32 C321 1.519(9) . ?
C33 C34 1.380(11) . ?
C33 H33 0.95 . ?
C34 C35 1.387(11) . ?
C34 H34 0.95 . ?
C35 C36 1.382(10) . ?
C35 H35 0.95 . ?
C36 C361 1.525(9) . ?
C221 C222 1.520(10) . ?
C221 C223 1.533(10) . ?
C221 H221 1 . ?
C222 H222 0.98 . ?
C222 H223 0.98 . ?
C222 H224 0.98 . ?
C223 H225 0.98 . ?
C223 H226 0.98 . ?
C223 H227 0.98 . ?
C261 C262 1.521(10) . ?
C261 C263 1.524(10) . ?
C261 H261 1 . ?
C262 H262 0.98 . ?
C262 H263 0.98 . ?
C262 H264 0.98 . ?
C263 H265 0.98 . ?
C263 H266 0.98 . ?
C263 H267 0.98 . ?
C321 C323 1.512(11) . ?
C321 C322 1.526(11) . ?
C321 H321 1 . ?
C322 H322 0.98 . ?
C322 H323 0.98 . ?
C322 H324 0.98 . ?
C323 H325 0.98 . ?
C323 H326 0.98 . ?
C323 H327 0.98 . ?
C361 C363 1.526(10) . ?
C361 C362 1.527(9) . ?
C361 H361 1 . ?
C362 H362 0.98 . ?
C362 H363 0.98 . ?
C362 H364 0.98 . ?
C363 H365 0.98 . ?
C363 H366 0.98 . ?
C363 H367 0.98 . ?
B1 F12 1.365(10) . ?
B1 F14 1.366(10) . ?
B1 F11 1.375(10) . ?
B1 F13 1.378(11) . ?
Cl11 C1 1.747(10) . ?
Cl12 C1 1.764(11) . ?
C1 H11 0.99 . ?
C1 H12 0.99 . ?

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
C12 Ir1 C21 165.1(2) . 7_556 ?
C12 Ir1 C22 156.3(2) . 7_556 ?
C21 Ir1 C22 38.2(2) 7_556 7_556 ?
C12 Ir1 C23 124.7(2) . 7_556 ?
C21 Ir1 C23 65.8(2) 7_556 7_556 ?
C22 Ir1 C23 36.6(2) 7_556 7_556 ?
C12 Ir1 C24 106.3(2) . 7_556 ?
C21 Ir1 C24 76.3(2) 7_556 7_556 ?
C22 Ir1 C24 65.3(2) 7_556 7_556 ?
C23 Ir1 C24 35.4(2) 7_556 7_556 ?
C12 Ir1 C26 131.0(2) . 7_556 ?
C21 Ir1 C26 36.6(2) 7_556 7_556 ?
C22 Ir1 C26 66.8(2) 7_556 7_556 ?
C23 Ir1 C26 75.6(2) 7_556 7_556 ?
C24 Ir1 C26 62.7(2) 7_556 7_556 ?
C12 Ir1 C25 109.6(2) . 7_556 ?
C21 Ir1 C25 63.8(2) 7_556 7_556 ?
C22 Ir1 C25 76.8(2) 7_556 7_556 ?
C23 Ir1 C25 63.2(2) 7_556 7_556 ?
C24 Ir1 C25 34.9(2) 7_556 7_556 ?
C26 Ir1 C25 34.1(2) 7_556 7_556 ?
C12 Ir1 Ir1 86.41(18) . 7_556 ?
C21 Ir1 Ir1 86.34(17) 7_556 7_556 ?
C22 Ir1 Ir1 110.23(17) 7_556 7_556 ?
C23 Ir1 Ir1 146.82(17) 7_556 7_556 ?
C24 Ir1 Ir1 155.51(17) 7_556 7_556 ?
C26 Ir1 Ir1 93.04(16) 7_556 7_556 ?
C25 Ir1 Ir1 121.37(16) 7_556 7_556 ?
C12 Ir1 H1 78(3) . . ?
C21 Ir1 H1 112(3) 7_556 . ?
C22 Ir1 H1 92(3) 7_556 . ?
C23 Ir1 H1 103(3) 7_556 . ?
C24 Ir1 H1 133(3) 7_556 . ?
C26 Ir1 H1 147(3) 7_556 . ?
C25 Ir1 H1 166(3) 7_556 . ?
Ir1 Ir1 H1 70(3) 7_556 . ?
C12 N11 C15 112.7(5) . . ?
C12 N11 C21 121.5(5) . . ?
C15 N11 C21 125.8(5) . . ?
N11 C12 N13 103.4(5) . . ?
N11 C12 Ir1 125.4(4) . . ?
N13 C12 Ir1 130.8(5) . . ?
C12 N13 C14 111.0(5) . . ?
C12 N13 C31 125.1(5) . . ?
C14 N13 C31 123.8(5) . . ?
C15 C14 N13 107.1(6) . . ?
C15 C14 H14 126.5 . . ?
N13 C14 H14 126.5 . . ?
C14 C15 N11 105.8(6) . . ?
C14 C15 H15 127.1 . . ?
N11 C15 H15 127.1 . . ?
C22 C21 N11 118.6(5) . . ?
C22 C21 C26 123.7(6) . . ?
N11 C21 C26 117.6(5) . . ?
C22 C21 Ir1 72.7(3) . 7_556 ?
N11 C21 Ir1 117.1(4) . 7_556 ?
C26 C21 Ir1 80.4(4) . 7_556 ?
C23 C22 C21 116.8(6) . . ?
C23 C22 C221 121.3(6) . . ?
C21 C22 C221 121.9(6) . . ?
C23 C22 Ir1 75.1(4) . 7_556 ?
C21 C22 Ir1 69.1(3) . 7_556 ?
C221 C22 Ir1 128.8(4) . 7_556 ?
C24 C23 C22 120.3(6) . . ?
C24 C23 Ir1 73.4(4) . 7_556 ?
C22 C23 Ir1 68.3(3) . 7_556 ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
Ir1 C23 H23 131.2 7_556 . ?
C23 C24 C25 121.3(6) . . ?
C23 C24 Ir1 71.1(4) . 7_556 ?
C25 C24 Ir1 75.4(4) . 7_556 ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
Ir1 C24 H24 126 7_556 . ?
C26 C25 C24 121.0(6) . . ?
C26 C25 Ir1 72.6(4) . 7_556 ?
C24 C25 Ir1 69.8(4) . 7_556 ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
Ir1 C25 H25 130.9 7_556 . ?
C25 C26 C21 116.2(6) . . ?
C25 C26 C261 121.9(6) . . ?
C21 C26 C261 122.0(6) . . ?
C25 C26 Ir1 73.3(4) . 7_556 ?
C21 C26 Ir1 63.1(3) . 7_556 ?
C261 C26 Ir1 133.5(5) . 7_556 ?
C36 C31 C32 124.2(6) . . ?
C36 C31 N13 117.8(6) . . ?
C32 C31 N13 118.0(6) . . ?
C33 C32 C31 116.1(6) . . ?
C33 C32 C321 121.2(6) . . ?
C31 C32 C321 122.5(6) . . ?
C34 C33 C32 121.4(7) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C33 C34 C35 120.4(7) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C36 C35 C34 120.8(7) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C35 C36 C31 117.0(6) . . ?
C35 C36 C361 121.7(6) . . ?
C31 C36 C361 121.3(6) . . ?
C222 C221 C22 113.5(6) . . ?
C222 C221 C223 110.2(6) . . ?
C22 C221 C223 107.5(6) . . ?
C222 C221 H221 108.5 . . ?
C22 C221 H221 108.5 . . ?
C223 C221 H221 108.5 . . ?
C221 C222 H222 109.5 . . ?
C221 C222 H223 109.5 . . ?
H222 C222 H223 109.5 . . ?
C221 C222 H224 109.5 . . ?
H222 C222 H224 109.5 . . ?
H223 C222 H224 109.5 . . ?
C221 C223 H225 109.5 . . ?
C221 C223 H226 109.5 . . ?
H225 C223 H226 109.5 . . ?
C221 C223 H227 109.5 . . ?
H225 C223 H227 109.5 . . ?
H226 C223 H227 109.5 . . ?
C26 C261 C262 113.2(6) . . ?
C26 C261 C263 109.3(6) . . ?
C262 C261 C263 110.6(6) . . ?
C26 C261 H261 107.9 . . ?
C262 C261 H261 107.9 . . ?
C263 C261 H261 107.9 . . ?
C261 C262 H262 109.5 . . ?
C261 C262 H263 109.5 . . ?
H262 C262 H263 109.5 . . ?
C261 C262 H264 109.5 . . ?
H262 C262 H264 109.5 . . ?
H263 C262 H264 109.5 . . ?
C261 C263 H265 109.5 . . ?
C261 C263 H266 109.5 . . ?
H265 C263 H266 109.5 . . ?
C261 C263 H267 109.5 . . ?
H265 C263 H267 109.5 . . ?
H266 C263 H267 109.5 . . ?
C323 C321 C32 113.1(7) . . ?
C323 C321 C322 109.6(7) . . ?
C32 C321 C322 110.1(6) . . ?
C323 C321 H321 108 . . ?
C32 C321 H321 108 . . ?
C322 C321 H321 108 . . ?
C321 C322 H322 109.5 . . ?
C321 C322 H323 109.5 . . ?
H322 C322 H323 109.5 . . ?
C321 C322 H324 109.5 . . ?
H322 C322 H324 109.5 . . ?
H323 C322 H324 109.5 . . ?
C321 C323 H325 109.5 . . ?
C321 C323 H326 109.5 . . ?
H325 C323 H326 109.5 . . ?
C321 C323 H327 109.5 . . ?
H325 C323 H327 109.5 . . ?
H326 C323 H327 109.5 . . ?
C36 C361 C363 112.4(5) . . ?
C36 C361 C362 113.6(6) . . ?
C363 C361 C362 108.6(6) . . ?
C36 C361 H361 107.3 . . ?
C363 C361 H361 107.3 . . ?
C362 C361 H361 107.3 . . ?
C361 C362 H362 109.5 . . ?
C361 C362 H363 109.5 . . ?
H362 C362 H363 109.5 . . ?
C361 C362 H364 109.5 . . ?
H362 C362 H364 109.5 . . ?
H363 C362 H364 109.5 . . ?
C361 C363 H365 109.5 . . ?
C361 C363 H366 109.5 . . ?
H365 C363 H366 109.5 . . ?
C361 C363 H367 109.5 . . ?
H365 C363 H367 109.5 . . ?
H366 C363 H367 109.5 . . ?
F12 B1 F14 110.8(8) . . ?
F12 B1 F11 109.4(7) . . ?
F14 B1 F11 108.3(8) . . ?
F12 B1 F13 110.8(8) . . ?
F14 B1 F13 106.9(7) . . ?
F11 B1 F13 110.6(7) . . ?
Cl11 C1 Cl12 110.7(5) . . ?
Cl11 C1 H11 109.5 . . ?
Cl12 C1 H11 109.5 . . ?
Cl11 C1 H12 109.5 . . ?
Cl12 C1 H12 109.5 . . ?
H11 C1 H12 108.1 . . ?

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
C15 N11 C12 N13 -0.2(7) . . . . ?
C21 N11 C12 N13 179.3(5) . . . . ?
C15 N11 C12 Ir1 -174.3(4) . . . . ?
C21 N11 C12 Ir1 5.2(8) . . . . ?
C21 Ir1 C12 N11 -75.2(11) 7_556 . . . ?
C22 Ir1 C12 N11 121.8(6) 7_556 . . . ?
C23 Ir1 C12 N11 153.3(5) 7_556 . . . ?
C24 Ir1 C12 N11 -172.9(5) 7_556 . . . ?
C26 Ir1 C12 N11 -105.1(5) 7_556 . . . ?
C25 Ir1 C12 N11 -136.3(5) 7_556 . . . ?
Ir1 Ir1 C12 N11 -14.2(5) 7_556 . . . ?
C21 Ir1 C12 N13 112.3(9) 7_556 . . . ?
C22 Ir1 C12 N13 -50.6(9) 7_556 . . . ?
C23 Ir1 C12 N13 -19.1(6) 7_556 . . . ?
C24 Ir1 C12 N13 14.7(6) 7_556 . . . ?
C26 Ir1 C12 N13 82.5(6) 7_556 . . . ?
C25 Ir1 C12 N13 51.3(6) 7_556 . . . ?
Ir1 Ir1 C12 N13 173.4(5) 7_556 . . . ?
N11 C12 N13 C14 0.2(6) . . . . ?
Ir1 C12 N13 C14 173.9(5) . . . . ?
N11 C12 N13 C31 -175.4(5) . . . . ?
Ir1 C12 N13 C31 -1.8(9) . . . . ?
C12 N13 C14 C15 -0.2(8) . . . . ?
C31 N13 C14 C15 175.5(6) . . . . ?
N13 C14 C15 N11 0.0(8) . . . . ?
C12 N11 C15 C14 0.1(8) . . . . ?
C21 N11 C15 C14 -179.4(6) . . . . ?
C12 N11 C21 C22 95.4(7) . . . . ?
C15 N11 C21 C22 -85.2(8) . . . . ?
C12 N11 C21 C26 -82.0(7) . . . . ?
C15 N11 C21 C26 97.5(7) . . . . ?
C12 N11 C21 Ir1 11.2(7) . . . 7_556 ?
C15 N11 C21 Ir1 -169.3(5) . . . 7_556 ?
N11 C21 C22 C23 -171.9(5) . . . . ?
C26 C21 C22 C23 5.3(9) . . . . ?
Ir1 C21 C22 C23 -59.9(5) 7_556 . . . ?
N11 C21 C22 C221 11.5(9) . . . . ?
C26 C21 C22 C221 -171.3(6) . . . . ?
Ir1 C21 C22 C221 123.5(6) 7_556 . . . ?
N11 C21 C22 Ir1 -111.9(5) . . . 7_556 ?
C26 C21 C22 Ir1 65.2(6) . . . 7_556 ?
C21 C22 C23 C24 2.8(9) . . . . ?
C221 C22 C23 C24 179.4(6) . . . . ?
Ir1 C22 C23 C24 -54.0(6) 7_556 . . . ?
C21 C22 C23 Ir1 56.8(5) . . . 7_556 ?
C221 C22 C23 Ir1 -126.6(6) . . . 7_556 ?
C22 C23 C24 C25 -7.0(10) . . . . ?
Ir1 C23 C24 C25 -58.6(6) 7_556 . . . ?
C22 C23 C24 Ir1 51.6(6) . . . 7_556 ?
C23 C24 C25 C26 3.0(10) . . . . ?
Ir1 C24 C25 C26 -53.6(6) 7_556 . . . ?
C23 C24 C25 Ir1 56.6(6) . . . 7_556 ?
C24 C25 C26 C21 4.7(9) . . . . ?
Ir1 C25 C26 C21 -47.6(5) 7_556 . . . ?
C24 C25 C26 C261 -176.4(6) . . . . ?
Ir1 C25 C26 C261 131.3(6) 7_556 . . . ?
C24 C25 C26 Ir1 52.3(6) . . . 7_556 ?
C22 C21 C26 C25 -9.0(9) . . . . ?
N11 C21 C26 C25 168.2(6) . . . . ?
Ir1 C21 C26 C25 52.6(5) 7_556 . . . ?
C22 C21 C26 C261 172.1(6) . . . . ?
N11 C21 C26 C261 -10.7(9) . . . . ?
Ir1 C21 C26 C261 -126.3(6) 7_556 . . . ?
C22 C21 C26 Ir1 -61.6(5) . . . 7_556 ?
N11 C21 C26 Ir1 115.6(5) . . . 7_556 ?
C12 N13 C31 C36 77.6(8) . . . . ?
C14 N13 C31 C36 -97.5(7) . . . . ?
C12 N13 C31 C32 -100.9(7) . . . . ?
C14 N13 C31 C32 84.0(8) . . . . ?
C36 C31 C32 C33 -1.9(10) . . . . ?
N13 C31 C32 C33 176.5(6) . . . . ?
C36 C31 C32 C321 174.0(6) . . . . ?
N13 C31 C32 C321 -7.6(9) . . . . ?
C31 C32 C33 C34 -1.6(10) . . . . ?
C321 C32 C33 C34 -177.5(7) . . . . ?
C32 C33 C34 C35 3.6(11) . . . . ?
C33 C34 C35 C36 -2.2(11) . . . . ?
C34 C35 C36 C31 -1.1(10) . . . . ?
C34 C35 C36 C361 177.8(6) . . . . ?
C32 C31 C36 C35 3.2(10) . . . . ?
N13 C31 C36 C35 -175.1(6) . . . . ?
C32 C31 C36 C361 -175.7(6) . . . . ?
N13 C31 C36 C361 6.0(9) . . . . ?
C23 C22 C221 C222 38.3(9) . . . . ?
C21 C22 C221 C222 -145.2(6) . . . . ?
Ir1 C22 C221 C222 -57.5(8) 7_556 . . . ?
C23 C22 C221 C223 -83.8(8) . . . . ?
C21 C22 C221 C223 92.7(8) . . . . ?
Ir1 C22 C221 C223 -179.6(5) 7_556 . . . ?
C25 C26 C261 C262 -24.4(9) . . . . ?
C21 C26 C261 C262 154.4(6) . . . . ?
Ir1 C26 C261 C262 72.8(8) 7_556 . . . ?
C25 C26 C261 C263 99.3(7) . . . . ?
C21 C26 C261 C263 -81.8(8) . . . . ?
Ir1 C26 C261 C263 -163.5(5) 7_556 . . . ?
C33 C32 C321 C323 -46.3(10) . . . . ?
C31 C32 C321 C323 138.0(8) . . . . ?
C33 C32 C321 C322 76.7(9) . . . . ?
C31 C32 C321 C322 -99.0(8) . . . . ?
C35 C36 C361 C363 -98.1(8) . . . . ?
C31 C36 C361 C363 80.8(8) . . . . ?
C35 C36 C361 C362 25.7(9) . . . . ?
C31 C36 C361 C362 -155.4(6) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
