#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/82/1518247.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1518247
loop_
_publ_author_name
'Wang, Chuanyong'
'Chen, Liang-An'
'Huo, Haohua'
'Shen, Xiaodong'
'Harms, Klaus'
'Gong, Lei'
'Meggers, Eric'
_publ_section_title
;
 Asymmetric Lewis acid catalysis directed by octahedral rhodium
 centrochirality
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              1094
_journal_paper_doi               10.1039/C4SC03101F
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C46 H43 Ir N4 O3, C H2 Cl2'
_chemical_formula_sum            'C47 H45 Cl2 Ir N4 O3'
_chemical_formula_weight         976.97
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 111.4793(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.9286(14)
_cell_length_b                   13.3583(5)
_cell_length_c                   17.0015(7)
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      25.2832
_cell_measurement_theta_min      2.2883
_cell_volume                     8227.1(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'BRUKER APEX2 2014.1-1'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      105(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            86572
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.304
_diffrn_reflns_theta_min         2.197
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.423
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3920
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         7482
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0237P)²+38.6963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0636
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6105
_reflns_number_total             7482
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4sc03101f2.cif
_cod_data_source_block           c75_0m
_cod_depositor_comments
'Adding full bibliography for 1518242--1518247.cif.'
_cod_database_code               1518247
#BEGIN Tags that were not found in dictionaries:
_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. 
;
_shelx_estimated_absorpt_t_min   0.665
_shelx_estimated_absorpt_t_max   0.935
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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'
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
C2 C 0.46804(12) 0.4476(3) 0.5670(3) 0.0247(10) Uani 1 1 d . . . . .
C4 C 0.47271(12) 0.6093(3) 0.5708(3) 0.0285(10) Uani 1 1 d . . . . .
C5 C 0.48502(13) 0.7066(4) 0.5853(3) 0.0387(13) Uani 1 1 d . . . . .
H5 H 0.5100 0.7227 0.6176 0.046 Uiso 1 1 calc R U . . .
C6 C 0.45860(13) 0.7792(3) 0.5498(3) 0.0333(11) Uani 1 1 d . . . . .
H6 H 0.4659 0.8475 0.5579 0.040 Uiso 1 1 calc R U . . .
C7 C 0.42165(11) 0.7573(3) 0.5023(3) 0.0212(9) Uani 1 1 d . . . . .
C8 C 0.41018(11) 0.6577(3) 0.4891(2) 0.0178(9) Uani 1 1 d . . . . .
H8 H 0.3853 0.6407 0.4569 0.021 Uiso 1 1 calc R U . . .
C9 C 0.43648(11) 0.5845(3) 0.5247(3) 0.0185(9) Uani 1 1 d . . . . .
C10 C 0.47557(12) 0.3420(3) 0.5755(3) 0.0259(10) Uani 1 1 d . . . . .
C11 C 0.44327(12) 0.2867(3) 0.5309(3) 0.0222(10) Uani 1 1 d . . . . .
C12 C 0.44818(13) 0.1821(3) 0.5334(3) 0.0315(11) Uani 1 1 d . . . . .
H12 H 0.4278 0.1403 0.5041 0.038 Uiso 1 1 calc R U . . .
C13 C 0.48207(14) 0.1391(4) 0.5777(3) 0.0430(13) Uani 1 1 d . . . . .
H13 H 0.4844 0.0683 0.5778 0.052 Uiso 1 1 calc R U . . .
C14 C 0.51272(14) 0.1963(4) 0.6217(4) 0.0465(14) Uani 1 1 d . . . . .
H14 H 0.5357 0.1651 0.6524 0.056 Uiso 1 1 calc R U . . .
C15 C 0.50956(13) 0.2989(4) 0.6206(3) 0.0394(13) Uani 1 1 d . . . . .
H15 H 0.5303 0.3396 0.6502 0.047 Uiso 1 1 calc R U . . .
C16 C 0.39343(12) 0.8419(3) 0.4682(3) 0.0250(10) Uani 1 1 d D U . . .
C17 C 0.36770(15) 0.8434(4) 0.5209(4) 0.0292(15) Uani 0.812(6) 1 d D U P A 1
H17A H 0.3483 0.8937 0.4975 0.044 Uiso 0.812(6) 1 calc R U P A 1
H17B H 0.3823 0.8601 0.5799 0.044 Uiso 0.812(6) 1 calc R U P A 1
H17C H 0.3564 0.7773 0.5184 0.044 Uiso 0.812(6) 1 calc R U P A 1
C18 C 0.36854(17) 0.8188(4) 0.3766(4) 0.0306(15) Uani 0.812(6) 1 d D U P A 1
H18A H 0.3508 0.8735 0.3546 0.046 Uiso 0.812(6) 1 calc R U P A 1
H18B H 0.3552 0.7561 0.3749 0.046 Uiso 0.812(6) 1 calc R U P A 1
H18C H 0.3837 0.8121 0.3419 0.046 Uiso 0.812(6) 1 calc R U P A 1
C19 C 0.41039(16) 0.9422(4) 0.4728(4) 0.0300(15) Uani 0.812(6) 1 d D U P A 1
H19A H 0.3909 0.9924 0.4494 0.045 Uiso 0.812(6) 1 calc R U P A 1
H19B H 0.4265 0.9420 0.4401 0.045 Uiso 0.812(6) 1 calc R U P A 1
H19C H 0.4249 0.9585 0.5319 0.045 Uiso 0.812(6) 1 calc R U P A 1
C17A C 0.3963(6) 0.9182(16) 0.5375(12) 0.031(5) Uani 0.188(6) 1 d D U P A 2
H17D H 0.3838 0.9803 0.5116 0.046 Uiso 0.188(6) 1 calc R U P A 2
H17E H 0.4224 0.9323 0.5702 0.046 Uiso 0.188(6) 1 calc R U P A 2
H17F H 0.3846 0.8910 0.5750 0.046 Uiso 0.188(6) 1 calc R U P A 2
C18A C 0.4063(6) 0.9084(17) 0.4030(14) 0.033(5) Uani 0.188(6) 1 d D U P A 2
H18D H 0.3902 0.9669 0.3843 0.049 Uiso 0.188(6) 1 calc R U P A 2
H18E H 0.4047 0.8676 0.3539 0.049 Uiso 0.188(6) 1 calc R U P A 2
H18F H 0.4319 0.9307 0.4319 0.049 Uiso 0.188(6) 1 calc R U P A 2
C19A C 0.3556(5) 0.8123(17) 0.4152(17) 0.035(6) Uani 0.188(6) 1 d D U P A 2
H19D H 0.3415 0.8719 0.3884 0.052 Uiso 0.188(6) 1 calc R U P A 2
H19E H 0.3438 0.7800 0.4504 0.052 Uiso 0.188(6) 1 calc R U P A 2
H19F H 0.3564 0.7655 0.3715 0.052 Uiso 0.188(6) 1 calc R U P A 2
C21 C 0.36097(11) 0.2234(3) 0.3547(3) 0.0203(9) Uani 1 1 d . . . . .
C23 C 0.32388(11) 0.1206(3) 0.3833(2) 0.0200(9) Uani 1 1 d . . . . .
C24 C 0.29903(11) 0.0474(3) 0.3813(3) 0.0234(10) Uani 1 1 d . . . . .
H24 H 0.2892 0.0030 0.3347 0.028 Uiso 1 1 calc R U . . .
C25 C 0.28898(11) 0.0419(3) 0.4515(3) 0.0236(10) Uani 1 1 d . . . . .
H25 H 0.2715 -0.0074 0.4523 0.028 Uiso 1 1 calc R U . . .
C26 C 0.30344(11) 0.1061(3) 0.5215(3) 0.0219(9) Uani 1 1 d . . . . .
C27 C 0.32909(11) 0.1787(3) 0.5214(2) 0.0186(9) Uani 1 1 d . . . . .
H27 H 0.3397 0.2223 0.5682 0.022 Uiso 1 1 calc R U . . .
C28 C 0.33867(10) 0.1852(3) 0.4508(2) 0.0164(9) Uani 1 1 d . . . . .
C29 C 0.38158(11) 0.2781(3) 0.3142(3) 0.0207(9) Uani 1 1 d . . . . .
C30 C 0.40135(11) 0.3573(3) 0.3663(3) 0.0204(9) Uani 1 1 d . . . . .
C31 C 0.42212(11) 0.4166(3) 0.3319(3) 0.0217(9) Uani 1 1 d . . . . .
H31 H 0.4360 0.4712 0.3637 0.026 Uiso 1 1 calc R U . . .
C32 C 0.42285(11) 0.3973(3) 0.2525(3) 0.0256(10) Uani 1 1 d . . . . .
H32 H 0.4372 0.4391 0.2312 0.031 Uiso 1 1 calc R U . . .
C33 C 0.40313(12) 0.3183(3) 0.2031(3) 0.0289(11) Uani 1 1 d . . . . .
H33 H 0.4043 0.3057 0.1492 0.035 Uiso 1 1 calc R U . . .
C34 C 0.38185(12) 0.2584(3) 0.2336(3) 0.0265(10) Uani 1 1 d . . . . .
H34 H 0.3677 0.2050 0.2005 0.032 Uiso 1 1 calc R U . . .
C35 C 0.29022(12) 0.0942(3) 0.5958(3) 0.0272(10) Uani 1 1 d . . . . .
C36 C 0.24838(12) 0.1159(4) 0.5648(3) 0.0356(12) Uani 1 1 d . . . . .
H36A H 0.2394 0.1023 0.6105 0.053 Uiso 1 1 calc R U . . .
H36B H 0.2354 0.0730 0.5163 0.053 Uiso 1 1 calc R U . . .
H36C H 0.2439 0.1863 0.5479 0.053 Uiso 1 1 calc R U . . .
C37 C 0.29770(13) -0.0135(4) 0.6300(3) 0.0371(12) Uani 1 1 d . . . . .
H37A H 0.2893 -0.0212 0.6773 0.056 Uiso 1 1 calc R U . . .
H37B H 0.3242 -0.0273 0.6494 0.056 Uiso 1 1 calc R U . . .
H37C H 0.2844 -0.0607 0.5850 0.056 Uiso 1 1 calc R U . . .
C38 C 0.30972(13) 0.1661(4) 0.6673(3) 0.0366(12) Uani 1 1 d . . . . .
H38A H 0.3010 0.1553 0.7138 0.055 Uiso 1 1 calc R U . . .
H38B H 0.3044 0.2351 0.6469 0.055 Uiso 1 1 calc R U . . .
H38C H 0.3364 0.1544 0.6874 0.055 Uiso 1 1 calc R U . . .
C40 C 0.39982(12) 0.3354(3) 0.6727(3) 0.0259(10) Uani 1 1 d . . . . .
H40 H 0.4188 0.2865 0.6918 0.031 Uiso 1 1 calc R U . . .
C41 C 0.38091(13) 0.3736(3) 0.7179(3) 0.0301(11) Uani 1 1 d . . . . .
H41 H 0.3840 0.3564 0.7743 0.036 Uiso 1 1 calc R U . . .
C43 C 0.36086(11) 0.4449(3) 0.5918(3) 0.0206(9) Uani 1 1 d . . . . .
C44 C 0.34182(11) 0.5010(3) 0.5124(3) 0.0200(9) Uani 1 1 d . . . . .
C45 C 0.31914(11) 0.5799(3) 0.5084(3) 0.0234(10) Uani 1 1 d . . . . .
H45 H 0.3176 0.6010 0.5603 0.028 Uiso 1 1 calc R U . . .
C46 C 0.29709(11) 0.6352(3) 0.4334(3) 0.0240(9) Uani 1 1 d . . . . .
C47 C 0.29270(11) 0.6073(3) 0.3509(3) 0.0239(10) Uani 1 1 d . . . . .
H47 H 0.3053 0.5501 0.3419 0.029 Uiso 1 1 calc R U . . .
C48 C 0.27026(12) 0.6623(3) 0.2824(3) 0.0293(11) Uani 1 1 d . . . . .
H48 H 0.2678 0.6421 0.2270 0.035 Uiso 1 1 calc R U . . .
C49 C 0.25135(13) 0.7459(3) 0.2924(3) 0.0336(11) Uani 1 1 d . . . . .
H49 H 0.2358 0.7824 0.2447 0.040 Uiso 1 1 calc R U . . .
C50 C 0.25556(12) 0.7750(3) 0.3732(3) 0.0347(12) Uani 1 1 d . . . . .
H50 H 0.2428 0.8324 0.3813 0.042 Uiso 1 1 calc R U . . .
C51 C 0.27823(12) 0.7214(3) 0.4430(3) 0.0299(11) Uani 1 1 d . . . . .
H51 H 0.2810 0.7434 0.4981 0.036 Uiso 1 1 calc R U . . .
C52 C 0.33088(13) 0.5002(4) 0.6956(3) 0.0349(12) Uani 1 1 d . . . . .
H52A H 0.3055 0.4896 0.6563 0.052 Uiso 1 1 calc R U . . .
H52B H 0.3370 0.5715 0.6970 0.052 Uiso 1 1 calc R U . . .
H52C H 0.3331 0.4784 0.7523 0.052 Uiso 1 1 calc R U . . .
C53 C 0.4444(2) 0.0229(8) 0.2342(6) 0.148(4) Uani 1 1 d D U . . .
H53A H 0.4420 0.0764 0.1923 0.177 Uiso 0.8 1 calc R U P B 1
H53B H 0.4653 -0.0201 0.2354 0.177 Uiso 0.8 1 calc R U P B 1
H53C H 0.4589 -0.0389 0.2550 0.177 Uiso 0.2 1 calc R U P C 2
H53D H 0.4352 0.0176 0.1718 0.177 Uiso 0.2 1 calc R U P C 2
N1 N 0.43448(9) 0.4796(2) 0.5243(2) 0.0188(8) Uani 1 1 d . . . . .
N20 N 0.36279(9) 0.2497(2) 0.4307(2) 0.0178(7) Uani 1 1 d . . . . .
N39 N 0.38699(9) 0.3795(2) 0.5941(2) 0.0211(8) Uani 1 1 d . . . . .
N42 N 0.35626(10) 0.4423(3) 0.6677(2) 0.0250(8) Uani 1 1 d . . . . .
O2 O 0.34989(7) 0.4666(2) 0.44858(17) 0.0187(6) Uani 1 1 d . . . . .
O3 O 0.49296(8) 0.5214(2) 0.5982(2) 0.0338(8) Uani 1 1 d . . . . .
O22 O 0.33821(8) 0.1445(2) 0.32177(17) 0.0222(6) Uani 1 1 d . . . . .
Ir1 Ir 0.39698(2) 0.36764(2) 0.48084(2) 0.01662(5) Uani 1 1 d . . . . .
Cl1 Cl 0.45608(6) 0.07809(15) 0.33096(16) 0.0732(8) Uani 0.754(3) 1 d D U P D 1
Cl2 Cl 0.40650(6) -0.04579(18) 0.19909(17) 0.0677(8) Uani 0.689(3) 1 d D U P D
1
Cl3 Cl 0.4737(2) 0.1010(6) 0.2520(5) 0.159(3) Uani 0.428(3) 1 d D U P D 2
Cl4 Cl 0.4066(3) 0.0012(10) 0.2549(9) 0.0677(8) Uani 0.128(2) 1 d D U P D 2
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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
N1 C2 O3 114.0(4) .
N1 C2 C10 120.0(4) .
O3 C2 C10 126.0(4) .
C5 C4 C9 123.0(4) .
C5 C4 O3 128.2(4) .
C9 C4 O3 108.8(4) .
C4 C5 C6 115.5(4) .
C4 C5 H5 122.3 .
C6 C5 H5 122.3 .
C5 C6 C7 123.2(4) .
C5 C6 H6 118.4 .
C7 C6 H6 118.4 .
C8 C7 C6 119.6(4) .
C8 C7 C16 119.9(4) .
C6 C7 C16 120.4(4) .
C9 C8 C7 117.5(4) .
C9 C8 H8 121.3 .
C7 C8 H8 121.3 .
C4 C9 C8 121.2(4) .
C4 C9 N1 106.6(4) .
C8 C9 N1 132.2(4) .
C15 C10 C11 124.0(4) .
C15 C10 C2 125.5(4) .
C11 C10 C2 110.5(4) .
C12 C11 C10 114.7(4) .
C12 C11 Ir1 129.7(3) .
C10 C11 Ir1 115.5(3) .
C13 C12 C11 121.4(4) .
C13 C12 H12 119.3 .
C11 C12 H12 119.3 .
C12 C13 C14 121.8(5) .
C12 C13 H13 119.1 .
C14 C13 H13 119.1 .
C15 C14 C13 119.2(5) .
C15 C14 H14 120.4 .
C13 C14 H14 120.4 .
C14 C15 C10 118.9(5) .
C14 C15 H15 120.6 .
C10 C15 H15 120.6 .
C19A C16 C17A 115.1(13) .
C19 C16 C18 109.8(4) .
C19A C16 C7 116.8(10) .
C19 C16 C7 113.7(4) .
C17A C16 C7 111.0(9) .
C18 C16 C7 109.6(4) .
C19 C16 C17 108.8(4) .
C18 C16 C17 106.5(4) .
C7 C16 C17 108.1(4) .
C19A C16 C18A 102.6(13) .
C17A C16 C18A 101.8(12) .
C7 C16 C18A 107.5(8) .
C16 C17 H17A 109.5 .
C16 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C16 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C16 C18 H18A 109.5 .
C16 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C16 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
C16 C19 H19A 109.5 .
C16 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C16 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C16 C17A H17D 109.5 .
C16 C17A H17E 109.5 .
H17D C17A H17E 109.5 .
C16 C17A H17F 109.5 .
H17D C17A H17F 109.5 .
H17E C17A H17F 109.5 .
C16 C18A H18D 109.5 .
C16 C18A H18E 109.5 .
H18D C18A H18E 109.5 .
C16 C18A H18F 109.5 .
H18D C18A H18F 109.5 .
H18E C18A H18F 109.5 .
C16 C19A H19D 109.5 .
C16 C19A H19E 109.5 .
H19D C19A H19E 109.5 .
C16 C19A H19F 109.5 .
H19D C19A H19F 109.5 .
H19E C19A H19F 109.5 .
N20 C21 O22 113.9(4) .
N20 C21 C29 119.8(4) .
O22 C21 C29 126.3(4) .
C24 C23 C28 122.9(4) .
C24 C23 O22 128.4(4) .
C28 C23 O22 108.7(3) .
C23 C24 C25 115.8(4) .
C23 C24 H24 122.1 .
C25 C24 H24 122.1 .
C24 C25 C26 123.0(4) .
C24 C25 H25 118.5 .
C26 C25 H25 118.5 .
C27 C26 C25 119.3(4) .
C27 C26 C35 121.9(4) .
C25 C26 C35 118.8(4) .
C28 C27 C26 117.7(4) .
C28 C27 H27 121.1 .
C26 C27 H27 121.1 .
C23 C28 C27 121.2(4) .
C23 C28 N20 107.1(3) .
C27 C28 N20 131.7(4) .
C34 C29 C30 123.8(4) .
C34 C29 C21 125.5(4) .
C30 C29 C21 110.6(4) .
C31 C30 C29 115.2(4) .
C31 C30 Ir1 128.9(3) .
C29 C30 Ir1 115.9(3) .
C32 C31 C30 121.5(4) .
C32 C31 H31 119.3 .
C30 C31 H31 119.3 .
C31 C32 C33 121.7(4) .
C31 C32 H32 119.1 .
C33 C32 H32 119.1 .
C34 C33 C32 119.2(4) .
C34 C33 H33 120.4 .
C32 C33 H33 120.4 .
C33 C34 C29 118.6(4) .
C33 C34 H34 120.7 .
C29 C34 H34 120.7 .
C38 C35 C26 111.9(4) .
C38 C35 C37 108.7(4) .
C26 C35 C37 109.4(4) .
C38 C35 C36 108.1(4) .
C26 C35 C36 109.2(4) .
C37 C35 C36 109.6(4) .
C35 C36 H36A 109.5 .
C35 C36 H36B 109.5 .
H36A C36 H36B 109.5 .
C35 C36 H36C 109.5 .
H36A C36 H36C 109.5 .
H36B C36 H36C 109.5 .
C35 C37 H37A 109.5 .
C35 C37 H37B 109.5 .
H37A C37 H37B 109.5 .
C35 C37 H37C 109.5 .
H37A C37 H37C 109.5 .
H37B C37 H37C 109.5 .
C35 C38 H38A 109.5 .
C35 C38 H38B 109.5 .
H38A C38 H38B 109.5 .
C35 C38 H38C 109.5 .
H38A C38 H38C 109.5 .
H38B C38 H38C 109.5 .
C41 C40 N39 108.2(4) .
C41 C40 H40 125.9 .
N39 C40 H40 125.9 .
C40 C41 N42 107.6(4) .
C40 C41 H41 126.2 .
N42 C41 H41 126.2 .
N39 C43 N42 108.6(4) .
N39 C43 C44 118.7(4) .
N42 C43 C44 132.7(4) .
O2 C44 C45 125.2(4) .
O2 C44 C43 112.5(4) .
C45 C44 C43 122.3(4) .
C44 C45 C46 127.0(4) .
C44 C45 H45 116.5 .
C46 C45 H45 116.5 .
C47 C46 C51 117.1(4) .
C47 C46 C45 124.1(4) .
C51 C46 C45 118.8(4) .
C48 C47 C46 120.7(4) .
C48 C47 H47 119.7 .
C46 C47 H47 119.7 .
C49 C48 C47 121.8(4) .
C49 C48 H48 119.1 .
C47 C48 H48 119.1 .
C50 C49 C48 118.4(5) .
C50 C49 H49 120.8 .
C48 C49 H49 120.8 .
C49 C50 C51 120.8(4) .
C49 C50 H50 119.6 .
C51 C50 H50 119.6 .
C50 C51 C46 121.3(4) .
C50 C51 H51 119.4 .
C46 C51 H51 119.4 .
N42 C52 H52A 109.5 .
N42 C52 H52B 109.5 .
H52A C52 H52B 109.5 .
N42 C52 H52C 109.5 .
H52A C52 H52C 109.5 .
H52B C52 H52C 109.5 .
Cl3 C53 Cl4 138.7(10) .
Cl2 C53 Cl1 118.5(6) .
Cl2 C53 H53A 107.7 .
Cl1 C53 H53A 107.7 .
Cl2 C53 H53B 107.7 .
Cl1 C53 H53B 107.7 .
H53A C53 H53B 107.1 .
Cl3 C53 H53C 102.4 .
Cl4 C53 H53C 102.4 .
Cl3 C53 H53D 102.4 .
Cl4 C53 H53D 102.4 .
H53C C53 H53D 104.9 .
C2 N1 C9 106.3(3) .
C2 N1 Ir1 113.5(3) .
C9 N1 Ir1 140.2(3) .
C21 N20 C28 105.9(3) .
C21 N20 Ir1 114.2(3) .
C28 N20 Ir1 139.8(3) .
C43 N39 C40 108.1(3) .
C43 N39 Ir1 114.7(3) .
C40 N39 Ir1 137.2(3) .
C43 N42 C41 107.5(4) .
C43 N42 C52 129.1(4) .
C41 N42 C52 123.5(4) .
C44 O2 Ir1 116.1(2) .
C2 O3 C4 104.3(3) .
C21 O22 C23 104.4(3) .
C11 Ir1 C30 89.56(16) .
C11 Ir1 N1 80.09(15) .
C30 Ir1 N1 95.62(15) .
C11 Ir1 N20 96.24(16) .
C30 Ir1 N20 79.40(15) .
N1 Ir1 N20 173.90(13) .
C11 Ir1 N39 95.20(15) .
C30 Ir1 N39 174.58(14) .
N1 Ir1 N39 87.77(13) .
N20 Ir1 N39 97.47(13) .
C11 Ir1 O2 169.97(14) .
C30 Ir1 O2 99.21(13) .
N1 Ir1 O2 94.13(12) .
N20 Ir1 O2 90.18(12) .
N39 Ir1 O2 76.27(11) .
C53 Cl3 Cl3 133.2(6) 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.312(5) .
C2 O3 1.348(5) .
C2 C10 1.437(6) .
C4 C5 1.375(6) .
C4 C9 1.380(6) .
C4 O3 1.396(5) .
C5 C6 1.382(6) .
C5 H5 0.9500 .
C6 C7 1.399(6) .
C6 H6 0.9500 .
C7 C8 1.395(6) .
C7 C16 1.535(6) .
C8 C9 1.384(6) .
C8 H8 0.9500 .
C9 N1 1.404(5) .
C10 C15 1.388(6) .
C10 C11 1.416(6) .
C11 C12 1.408(6) .
C11 Ir1 2.004(4) .
C12 C13 1.382(6) .
C12 H12 0.9500 .
C13 C14 1.383(7) .
C13 H13 0.9500 .
C14 C15 1.376(7) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C19A 1.471(15) .
C16 C19 1.483(6) .
C16 C17A 1.531(15) .
C16 C18 1.534(7) .
C16 C17 1.570(7) .
C16 C18A 1.636(16) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C17A H17D 0.9800 .
C17A H17E 0.9800 .
C17A H17F 0.9800 .
C18A H18D 0.9800 .
C18A H18E 0.9800 .
C18A H18F 0.9800 .
C19A H19D 0.9800 .
C19A H19E 0.9800 .
C19A H19F 0.9800 .
C21 N20 1.314(5) .
C21 O22 1.359(5) .
C21 C29 1.434(6) .
C23 C24 1.367(6) .
C23 C28 1.381(5) .
C23 O22 1.392(5) .
C24 C25 1.387(6) .
C24 H24 0.9500 .
C25 C26 1.405(6) .
C25 H25 0.9500 .
C26 C27 1.393(6) .
C26 C35 1.538(6) .
C27 C28 1.384(5) .
C27 H27 0.9500 .
C28 N20 1.406(5) .
C29 C34 1.400(6) .
C29 C30 1.413(6) .
C30 C31 1.404(6) .
C30 Ir1 2.021(4) .
C31 C32 1.384(6) .
C31 H31 0.9500 .
C32 C33 1.391(6) .
C32 H32 0.9500 .
C33 C34 1.381(6) .
C33 H33 0.9500 .
C34 H34 0.9500 .
C35 C38 1.517(6) .
C35 C37 1.539(6) .
C35 C36 1.545(6) .
C36 H36A 0.9800 .
C36 H36B 0.9800 .
C36 H36C 0.9800 .
C37 H37A 0.9800 .
C37 H37B 0.9800 .
C37 H37C 0.9800 .
C38 H38A 0.9800 .
C38 H38B 0.9800 .
C38 H38C 0.9800 .
C40 C41 1.344(6) .
C40 N39 1.376(5) .
C40 H40 0.9500 .
C41 N42 1.375(6) .
C41 H41 0.9500 .
C43 N39 1.331(5) .
C43 N42 1.366(5) .
C43 C44 1.485(6) .
C44 O2 1.318(5) .
C44 C45 1.360(6) .
C45 C46 1.452(6) .
C45 H45 0.9500 .
C46 C47 1.400(6) .
C46 C51 1.406(6) .
C47 C48 1.384(6) .
C47 H47 0.9500 .
C48 C49 1.381(6) .
C48 H48 0.9500 .
C49 C50 1.380(7) .
C49 H49 0.9500 .
C50 C51 1.390(6) .
C50 H50 0.9500 .
C51 H51 0.9500 .
C52 N42 1.464(6) .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 0.9800 .
C53 Cl3 1.494(8) .
C53 Cl2 1.651(7) .
C53 Cl4 1.656(12) .
C53 Cl1 1.705(9) .
C53 H53A 0.9900 .
C53 H53B 0.9900 .
C53 H53C 0.9900 .
C53 H53D 0.9900 .
N1 Ir1 2.031(3) .
N20 Ir1 2.037(3) .
N39 Ir1 2.105(3) .
O2 Ir1 2.161(3) .
Cl3 Cl3 2.072(15) 2_655
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_4
C9 C4 C5 C6 -0.7(8) .
O3 C4 C5 C6 179.7(5) .
C4 C5 C6 C7 0.3(8) .
C5 C6 C7 C8 -0.2(7) .
C5 C6 C7 C16 177.2(5) .
C6 C7 C8 C9 0.3(6) .
C16 C7 C8 C9 -177.0(4) .
C5 C4 C9 C8 0.8(7) .
O3 C4 C9 C8 -179.5(4) .
C5 C4 C9 N1 -179.4(5) .
O3 C4 C9 N1 0.3(5) .
C7 C8 C9 C4 -0.6(6) .
C7 C8 C9 N1 179.7(4) .
N1 C2 C10 C15 -178.4(5) .
O3 C2 C10 C15 3.0(8) .
N1 C2 C10 C11 1.9(6) .
O3 C2 C10 C11 -176.7(4) .
C15 C10 C11 C12 -1.6(7) .
C2 C10 C11 C12 178.2(4) .
C15 C10 C11 Ir1 174.3(4) .
C2 C10 C11 Ir1 -6.0(5) .
C10 C11 C12 C13 1.0(7) .
Ir1 C11 C12 C13 -174.2(4) .
C11 C12 C13 C14 0.3(8) .
C12 C13 C14 C15 -0.9(9) .
C13 C14 C15 C10 0.3(9) .
C11 C10 C15 C14 1.0(8) .
C2 C10 C15 C14 -178.8(5) .
C8 C7 C16 C19A -5.8(14) .
C6 C7 C16 C19A 176.9(14) .
C8 C7 C16 C19 -169.2(4) .
C6 C7 C16 C19 13.5(6) .
C8 C7 C16 C17A 129.0(10) .
C6 C7 C16 C17A -48.3(11) .
C8 C7 C16 C18 -45.9(6) .
C6 C7 C16 C18 136.8(5) .
C8 C7 C16 C17 69.8(5) .
C6 C7 C16 C17 -107.5(5) .
C8 C7 C16 C18A -120.4(10) .
C6 C7 C16 C18A 62.3(11) .
C28 C23 C24 C25 0.6(6) .
O22 C23 C24 C25 -178.6(4) .
C23 C24 C25 C26 -0.8(6) .
C24 C25 C26 C27 -0.1(6) .
C24 C25 C26 C35 179.5(4) .
C25 C26 C27 C28 1.1(6) .
C35 C26 C27 C28 -178.5(4) .
C24 C23 C28 C27 0.4(6) .
O22 C23 C28 C27 179.8(3) .
C24 C23 C28 N20 -179.8(4) .
O22 C23 C28 N20 -0.4(4) .
C26 C27 C28 C23 -1.2(6) .
C26 C27 C28 N20 179.0(4) .
N20 C21 C29 C34 -179.5(4) .
O22 C21 C29 C34 -0.5(7) .
N20 C21 C29 C30 -0.8(5) .
O22 C21 C29 C30 178.2(4) .
C34 C29 C30 C31 -0.4(6) .
C21 C29 C30 C31 -179.1(3) .
C34 C29 C30 Ir1 -178.9(3) .
C21 C29 C30 Ir1 2.4(4) .
C29 C30 C31 C32 -0.2(6) .
Ir1 C30 C31 C32 178.1(3) .
C30 C31 C32 C33 -0.1(6) .
C31 C32 C33 C34 0.9(7) .
C32 C33 C34 C29 -1.5(6) .
C30 C29 C34 C33 1.3(6) .
C21 C29 C34 C33 179.8(4) .
C27 C26 C35 C38 -2.8(6) .
C25 C26 C35 C38 177.6(4) .
C27 C26 C35 C37 -123.3(4) .
C25 C26 C35 C37 57.1(5) .
C27 C26 C35 C36 116.8(4) .
C25 C26 C35 C36 -62.8(5) .
N39 C40 C41 N42 -0.3(5) .
N39 C43 C44 O2 9.7(5) .
N42 C43 C44 O2 -167.1(4) .
N39 C43 C44 C45 -169.4(4) .
N42 C43 C44 C45 13.8(7) .
O2 C44 C45 C46 5.9(7) .
C43 C44 C45 C46 -175.1(4) .
C44 C45 C46 C47 7.8(7) .
C44 C45 C46 C51 -173.4(4) .
C51 C46 C47 C48 -0.9(6) .
C45 C46 C47 C48 178.0(4) .
C46 C47 C48 C49 -0.2(7) .
C47 C48 C49 C50 0.8(7) .
C48 C49 C50 C51 -0.2(7) .
C49 C50 C51 C46 -1.0(7) .
C47 C46 C51 C50 1.5(6) .
C45 C46 C51 C50 -177.4(4) .
O3 C2 N1 C9 1.1(5) .
C10 C2 N1 C9 -177.7(4) .
O3 C2 N1 Ir1 -178.2(3) .
C10 C2 N1 Ir1 3.0(5) .
C4 C9 N1 C2 -0.8(5) .
C8 C9 N1 C2 178.9(4) .
C4 C9 N1 Ir1 178.2(3) .
C8 C9 N1 Ir1 -2.1(8) .
O22 C21 N20 C28 -1.4(5) .
C29 C21 N20 C28 177.6(3) .
O22 C21 N20 Ir1 179.8(2) .
C29 C21 N20 Ir1 -1.1(5) .
C23 C28 N20 C21 1.1(4) .
C27 C28 N20 C21 -179.1(4) .
C23 C28 N20 Ir1 179.4(3) .
C27 C28 N20 Ir1 -0.9(7) .
N42 C43 N39 C40 -1.0(4) .
C44 C43 N39 C40 -178.5(3) .
N42 C43 N39 Ir1 177.7(2) .
C44 C43 N39 Ir1 0.2(4) .
C41 C40 N39 C43 0.8(5) .
C41 C40 N39 Ir1 -177.5(3) .
N39 C43 N42 C41 0.8(4) .
C44 C43 N42 C41 177.9(4) .
N39 C43 N42 C52 -180.0(4) .
C44 C43 N42 C52 -2.9(7) .
C40 C41 N42 C43 -0.3(5) .
C40 C41 N42 C52 -179.6(4) .
C45 C44 O2 Ir1 164.5(3) .
C43 C44 O2 Ir1 -14.6(4) .
N1 C2 O3 C4 -0.9(5) .
C10 C2 O3 C4 177.8(4) .
C5 C4 O3 C2 180.0(5) .
C9 C4 O3 C2 0.3(5) .
N20 C21 O22 C23 1.2(4) .
C29 C21 O22 C23 -177.8(4) .
C24 C23 O22 C21 179.0(4) .
C28 C23 O22 C21 -0.4(4) .
Cl2 C53 Cl3 Cl3 -121(4) 2_655
Cl4 C53 Cl3 Cl3 161.3(11) 2_655
Cl1 C53 Cl3 Cl3 126.4(9) 2_655
