#------------------------------------------------------------------------------
#$Date: 2017-04-06 05:03:44 +0300 (Thu, 06 Apr 2017) $
#$Revision: 195222 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/56/1545688.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_1545688
loop_
_publ_author_name
'Perez, laura Rubio'
'Iglesias, Manuel'
'Munarriz, Julen'
'Polo, Victor'
'Passarelli, Vincenzo'
'Pérez-Torrente, Jesús J. J.'
'Oro, Luis A.'
_publ_section_title
;
 A Well-Defined NHC-Ir(III) Catalyst for the Silylation of Aromatic C--H
 Bonds: Substrate Survey and Mechanistic Insights
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C6SC04899D
_journal_year                    2017
_chemical_formula_moiety         '2 (C46 H53 Ir N5 S), 2 (B F4), 3 (C H2 Cl2)'
_chemical_formula_sum            'C95 H112 B2 Cl6 F8 Ir2 N10 S2'
_chemical_formula_weight         2228.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-10-03 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.3290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   21.1207(14)
_cell_length_b                   11.2623(8)
_cell_length_c                   22.7007(15)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.637
_cell_measurement_theta_min      2.219
_cell_volume                     4920.2(6)
_computing_cell_refinement       'APEX2 v. 2009.7 (Bruker AXS, 2008)'
_computing_data_collection       'APEX2 v. 2009.7 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 v. 2009.7 (Bruker AXS, 2008)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker APEX CCD system'
_diffrn_measurement_method       'narrow ω frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            55195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.570
_diffrn_reflns_theta_min         2.059
_exptl_absorpt_coefficient_mu    2.972
_exptl_absorpt_correction_T_max  0.6120
_exptl_absorpt_correction_T_min  0.4973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS 
 within APEX2 package. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       prism
_exptl_crystal_F_000             2244
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.607
_refine_diff_density_min         -1.526
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         11624
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0364P)²+20.2845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9457
_reflns_number_total             11624
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6sc04899d2.cif
_cod_data_source_block           VPX87_LPR343
_cod_database_code               1545688
_shelx_shelxl_version_number     2014/7
_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'
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
B1A B 0.3291(6) 0.7381(9) 0.9360(6) 0.056(2) Uani 0.583(7) 1 d D . P A 1
F1A F 0.3533(5) 0.7465(7) 1.0013(4) 0.0851(18) Uani 0.583(7) 1 d D . P A 1
F2A F 0.3210(5) 0.6218(6) 0.9213(4) 0.0851(18) Uani 0.583(7) 1 d D . P A 1
F3A F 0.2685(4) 0.7998(6) 0.9122(4) 0.0851(18) Uani 0.583(7) 1 d D . P A 1
F4A F 0.3707(4) 0.7880(6) 0.9120(4) 0.0851(18) Uani 0.583(7) 1 d D . P A 1
B1B B 0.3180(7) 0.7289(11) 0.9286(7) 0.056(2) Uani 0.417(7) 1 d D . P A 2
F1B F 0.3214(5) 0.7359(9) 0.9921(5) 0.064(2) Uani 0.417(7) 1 d D . P A 2
F2B F 0.2654(5) 0.6489(7) 0.8914(5) 0.064(2) Uani 0.417(7) 1 d D . P A 2
F3B F 0.3028(5) 0.8415(7) 0.8994(5) 0.064(2) Uani 0.417(7) 1 d D . P A 2
F4B F 0.3785(5) 0.6886(7) 0.9243(5) 0.064(2) Uani 0.417(7) 1 d D . P A 2
C1SA C 0.1590(9) 0.6570(11) 0.2590(8) 0.114(5) Uiso 0.672(6) 1 d D . P B 3
H1S1 H 0.1490 0.6279 0.2149 0.137 Uiso 0.672(6) 1 calc R U P B 3
H1S2 H 0.2083 0.6815 0.2807 0.137 Uiso 0.672(6) 1 calc R U P B 3
Cl1A Cl 0.0955(4) 0.7847(6) 0.2583(3) 0.164(3) Uiso 0.672(6) 1 d D . P B 3
Cl2A Cl 0.1356(3) 0.5450(6) 0.3075(3) 0.162(3) Uiso 0.672(6) 1 d D . P B 3
C1SB C 0.0601(15) 0.7338(19) 0.2928(13) 0.095(9) Uiso 0.328(6) 1 d D . P B 2
H1S3 H 0.0223 0.6748 0.2832 0.114 Uiso 0.328(6) 1 calc R U P B 2
H1S4 H 0.0928 0.7282 0.3389 0.114 Uiso 0.328(6) 1 calc R U P B 2
Cl1B Cl 0.0256(6) 0.8884(10) 0.2696(5) 0.139(4) Uiso 0.328(6) 1 d D . P B 2
Cl2B Cl 0.1066(9) 0.7181(16) 0.2358(8) 0.210(7) Uiso 0.328(6) 1 d D . P B 2
Cl4 Cl 0.4721(3) 0.9626(9) 0.0731(3) 0.149(4) Uani 0.5 1 d . . P . .
C2S C 0.4618(10) 0.9200(17) -0.0029(9) 0.087(5) Uani 0.5 1 d . . P . .
H2S1 H 0.4135 0.9367 -0.0339 0.105 Uiso 0.5 1 calc R U P . .
H2S2 H 0.4696 0.8334 -0.0032 0.105 Uiso 0.5 1 calc R U P . .
Cl3 Cl 0.4794(3) 1.0042(5) 0.0285(3) 0.1066(18) Uani 0.5 1 d . . P . .
C1 C 0.2670(2) 0.1801(4) 0.0573(2) 0.0203(8) Uani 1 1 d . . . . .
C3 C 0.2599(2) 0.0351(4) -0.0157(2) 0.0264(9) Uani 1 1 d . . . . .
H3 H 0.2530 -0.0021 -0.0555 0.032 Uiso 1 1 calc R U . . .
C4 C 0.2810(2) -0.0180(4) 0.0420(2) 0.0267(9) Uani 1 1 d . . . . .
H4 H 0.2920 -0.0997 0.0510 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2847(2) 0.0355(3) 0.1480(2) 0.0231(9) Uani 1 1 d . . . . .
C7 C 0.2214(2) 0.0015(4) 0.1491(2) 0.0275(9) Uani 1 1 d . . . . .
C8 C 0.2220(3) -0.0362(4) 0.2080(3) 0.0365(12) Uani 1 1 d . . . . .
H8 H 0.1798 -0.0599 0.2101 0.044 Uiso 1 1 calc R U . . .
C9 C 0.2828(3) -0.0395(4) 0.2630(3) 0.0384(13) Uani 1 1 d . . . . .
H9 H 0.2821 -0.0632 0.3029 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3450(3) -0.0086(4) 0.2605(2) 0.0349(11) Uani 1 1 d . . . . .
H10 H 0.3867 -0.0120 0.2988 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3477(3) 0.0274(4) 0.2031(2) 0.0285(10) Uani 1 1 d . . . . .
C12 C 0.1545(2) -0.0059(5) 0.0882(2) 0.0334(11) Uani 1 1 d . . . . .
H12 H 0.1622 0.0364 0.0530 0.040 Uiso 1 1 calc R U . . .
C13 C 0.0923(3) 0.0513(6) 0.0944(3) 0.0520(16) Uani 1 1 d . . . . .
H13A H 0.0817 0.0082 0.1268 0.078 Uiso 1 1 calc R U . . .
H13B H 0.0520 0.0483 0.0526 0.078 Uiso 1 1 calc R U . . .
H13C H 0.1031 0.1342 0.1079 0.078 Uiso 1 1 calc R U . . .
C14 C 0.1388(3) -0.1372(5) 0.0680(3) 0.0473(14) Uani 1 1 d . . . . .
H14A H 0.1284 -0.1799 0.1005 0.071 Uiso 1 1 calc R U . . .
H14B H 0.1794 -0.1732 0.0645 0.071 Uiso 1 1 calc R U . . .
H14C H 0.0987 -0.1419 0.0261 0.071 Uiso 1 1 calc R U . . .
C15 C 0.4176(2) 0.0458(4) 0.2005(3) 0.0335(11) Uani 1 1 d . . . . .
H15 H 0.4091 0.0760 0.1565 0.040 Uiso 1 1 calc R U . . .
C16 C 0.4557(3) -0.0740(5) 0.2103(4) 0.0582(18) Uani 1 1 d . . . . .
H16A H 0.4681 -0.1020 0.2545 0.087 Uiso 1 1 calc R U . . .
H16B H 0.4979 -0.0640 0.2029 0.087 Uiso 1 1 calc R U . . .
H16C H 0.4252 -0.1323 0.1796 0.087 Uiso 1 1 calc R U . . .
C17 C 0.4632(3) 0.1360(5) 0.2501(3) 0.0471(15) Uani 1 1 d . . . . .
H17A H 0.4380 0.2112 0.2444 0.071 Uiso 1 1 calc R U . . .
H17B H 0.5059 0.1490 0.2440 0.071 Uiso 1 1 calc R U . . .
H17C H 0.4749 0.1056 0.2938 0.071 Uiso 1 1 calc R U . . .
C18 C 0.2181(2) 0.2328(4) -0.0622(2) 0.0252(9) Uani 1 1 d . . . . .
C19 C 0.1466(2) 0.2569(4) -0.0846(2) 0.0285(10) Uani 1 1 d . . . . .
C20 C 0.1168(3) 0.3274(5) -0.1398(2) 0.0361(11) Uani 1 1 d . . . . .
H20 H 0.0690 0.3474 -0.1555 0.043 Uiso 1 1 calc R U . . .
C21 C 0.1552(3) 0.3687(5) -0.1722(2) 0.0394(12) Uani 1 1 d . . . . .
H21 H 0.1337 0.4168 -0.2096 0.047 Uiso 1 1 calc R U . . .
C22 C 0.2249(3) 0.3401(4) -0.1503(2) 0.0350(11) Uani 1 1 d . . . . .
H22 H 0.2507 0.3681 -0.1732 0.042 Uiso 1 1 calc R U . . .
C23 C 0.2579(3) 0.2709(4) -0.0951(2) 0.0288(10) Uani 1 1 d . . . . .
C24 C 0.1023(2) 0.2029(5) -0.0533(3) 0.0338(11) Uani 1 1 d . . . . .
H24 H 0.1305 0.2006 -0.0055 0.041 Uiso 1 1 calc R U . . .
C25 C 0.0830(3) 0.0747(5) -0.0773(3) 0.0434(13) Uani 1 1 d . . . . .
H25A H 0.0559 0.0750 -0.1243 0.065 Uiso 1 1 calc R U . . .
H25B H 0.0553 0.0393 -0.0562 0.065 Uiso 1 1 calc R U . . .
H25C H 0.1255 0.0282 -0.0668 0.065 Uiso 1 1 calc R U . . .
C26 C 0.0353(3) 0.2724(5) -0.0663(3) 0.0428(13) Uani 1 1 d . . . . .
H26A H 0.0463 0.3570 -0.0580 0.064 Uiso 1 1 calc R U . . .
H26B H 0.0144 0.2432 -0.0378 0.064 Uiso 1 1 calc R U . . .
H26C H 0.0026 0.2614 -0.1115 0.064 Uiso 1 1 calc R U . . .
C27 C 0.3323(2) 0.2331(4) -0.0764(2) 0.0286(10) Uani 1 1 d . . . . .
H27 H 0.3509 0.2002 -0.0315 0.034 Uiso 1 1 calc R U . . .
C28 C 0.3786(3) 0.3372(5) -0.0779(3) 0.0385(12) Uani 1 1 d . . . . .
H28A H 0.4271 0.3111 -0.0608 0.058 Uiso 1 1 calc R U . . .
H28B H 0.3740 0.4025 -0.0514 0.058 Uiso 1 1 calc R U . . .
H28C H 0.3641 0.3645 -0.1226 0.058 Uiso 1 1 calc R U . . .
C29 C 0.3358(3) 0.1357(5) -0.1222(3) 0.0386(12) Uani 1 1 d . . . . .
H29A H 0.3146 0.1649 -0.1668 0.058 Uiso 1 1 calc R U . . .
H29B H 0.3105 0.0654 -0.1182 0.058 Uiso 1 1 calc R U . . .
H29C H 0.3844 0.1148 -0.1109 0.058 Uiso 1 1 calc R U . . .
C30 C 0.2047(2) 0.3266(4) 0.1312(2) 0.0256(9) Uani 1 1 d . . . . .
C31 C 0.1981(3) 0.2805(4) 0.1868(2) 0.0315(10) Uani 1 1 d . . . . .
H31 H 0.2313 0.2290 0.2170 0.038 Uiso 1 1 calc R U . . .
C32 C 0.1390(3) 0.3177(5) 0.1922(3) 0.0467(14) Uani 1 1 d . . . . .
H32 H 0.1270 0.2953 0.2266 0.056 Uiso 1 1 calc R U . . .
C34 C 0.1494(2) 0.4001(4) 0.0966(2) 0.0310(10) Uani 1 1 d . . . . .
C35 C 0.1494(2) 0.4695(4) 0.0434(2) 0.0313(10) Uani 1 1 d . . . . .
C37 C 0.2118(3) 0.5108(4) -0.0181(2) 0.0334(11) Uani 1 1 d . . . . .
H37 H 0.2504 0.4950 -0.0283 0.040 Uiso 1 1 calc R U . . .
C38 C 0.1644(3) 0.5974(5) -0.0533(3) 0.0429(14) Uani 1 1 d . . . . .
H38 H 0.1707 0.6406 -0.0864 0.052 Uiso 1 1 calc R U . . .
C39 C 0.1079(3) 0.6192(5) -0.0388(3) 0.0470(14) Uani 1 1 d . . . . .
H39 H 0.0748 0.6780 -0.0621 0.056 Uiso 1 1 calc R U . . .
C40 C 0.0999(3) 0.5557(5) 0.0092(3) 0.0396(12) Uani 1 1 d . . . . .
H40 H 0.0611 0.5700 0.0193 0.048 Uiso 1 1 calc R U . . .
C42 C 0.3469(2) 0.4708(4) 0.2297(2) 0.0264(9) Uani 1 1 d . . . . .
H42 H 0.3600 0.3918 0.2445 0.032 Uiso 1 1 calc R U . . .
C43 C 0.3640(3) 0.5608(4) 0.2751(2) 0.0340(11) Uani 1 1 d . . . . .
H43 H 0.3887 0.5436 0.3198 0.041 Uiso 1 1 calc R U . . .
C44 C 0.3448(3) 0.6753(4) 0.2548(2) 0.0361(11) Uani 1 1 d . . . . .
H44 H 0.3551 0.7385 0.2851 0.043 Uiso 1 1 calc R U . . .
C45 C 0.3099(3) 0.6964(4) 0.1890(3) 0.0389(12) Uani 1 1 d . . . . .
H45 H 0.2970 0.7747 0.1732 0.047 Uiso 1 1 calc R U . . .
C46 C 0.2944(3) 0.6012(4) 0.1470(2) 0.0326(11) Uani 1 1 d . . . . .
H46 H 0.2692 0.6162 0.1021 0.039 Uiso 1 1 calc R U . . .
C48 C 0.4209(2) 0.2907(5) 0.0893(2) 0.0294(10) Uani 1 1 d . . . . .
H48 H 0.4106 0.2110 0.0958 0.035 Uiso 1 1 calc R U . . .
C49 C 0.4844(3) 0.3145(6) 0.0880(2) 0.0414(13) Uani 1 1 d . . . . .
H49 H 0.5170 0.2525 0.0940 0.050 Uiso 1 1 calc R U . . .
C50 C 0.4998(3) 0.4303(6) 0.0776(2) 0.0464(15) Uani 1 1 d . . . . .
H50 H 0.5432 0.4492 0.0766 0.056 Uiso 1 1 calc R U . . .
C51 C 0.4509(3) 0.5170(5) 0.0688(3) 0.0449(14) Uani 1 1 d . . . . .
H51 H 0.4598 0.5968 0.0611 0.054 Uiso 1 1 calc R U . . .
C52 C 0.3883(3) 0.4868(5) 0.0713(2) 0.0380(12) Uani 1 1 d . . . . .
H52 H 0.3550 0.5476 0.0651 0.046 Uiso 1 1 calc R U . . .
N2 N 0.25008(19) 0.1550(3) -0.00677(17) 0.0230(7) Uani 1 1 d . . . . .
N5 N 0.28380(18) 0.0697(3) 0.08618(18) 0.0227(8) Uani 1 1 d . . . . .
N36 N 0.2056(2) 0.4482(3) 0.02982(18) 0.0266(8) Uani 1 1 d . . . . .
N41 N 0.31288(19) 0.4890(3) 0.16573(17) 0.0235(7) Uani 1 1 d . . . . .
N47 N 0.3728(2) 0.3751(3) 0.08198(18) 0.0266(8) Uani 1 1 d . . . . .
S33 S 0.08933(8) 0.40945(16) 0.13011(8) 0.0513(4) Uani 1 1 d . . . . .
Ir1 Ir 0.28361(2) 0.33661(2) 0.10345(2) 0.02035(6) Uani 1 1 d D . . . .
H1 H 0.3362(18) 0.264(3) 0.1645(14) 0.021(12) Uiso 1 1 d D . . . .
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'
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'
S S 0.1246 0.1234 '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_1
_geom_angle_site_symmetry_3
F4A B1A F2A 110.4(8) . .
F4A B1A F3A 107.1(9) . .
F2A B1A F3A 113.4(10) . .
F4A B1A F1A 113.6(10) . .
F2A B1A F1A 106.9(8) . .
F3A B1A F1A 105.5(8) . .
F4B B1B F3B 107.4(9) . .
F4B B1B F2B 105.6(9) . .
F3B B1B F2B 108.9(10) . .
F4B B1B F1B 115.1(10) . .
F3B B1B F1B 109.6(9) . .
F2B B1B F1B 110.0(9) . .
Cl2A C1SA Cl1A 98.8(8) . .
Cl2A C1SA H1S1 112.0 . .
Cl1A C1SA H1S1 112.0 . .
Cl2A C1SA H1S2 112.0 . .
Cl1A C1SA H1S2 112.0 . .
H1S1 C1SA H1S2 109.7 . .
Cl1B C1SB Cl2B 98.2(11) . .
Cl1B C1SB H1S3 112.1 . .
Cl2B C1SB H1S3 112.1 . .
Cl1B C1SB H1S4 112.1 . .
Cl2B C1SB H1S4 112.1 . .
H1S3 C1SB H1S4 109.8 . .
Cl3 Cl4 C2S 42.0(7) . .
Cl4 C2S Cl3 112.0(12) . 3_675
Cl4 C2S H2S1 109.2 . .
Cl3 C2S H2S1 109.2 3_675 .
Cl4 C2S H2S2 109.2 . .
Cl3 C2S H2S2 109.2 3_675 .
H2S1 C2S H2S2 107.9 . .
Cl4 Cl3 C2S 145.0(8) . 3_675
Cl4 Cl3 Cl3 148.2(8) . 3_675
C2S Cl3 Cl3 37.0(6) 3_675 3_675
N2 C1 N5 102.8(3) . .
N2 C1 Ir1 130.3(3) . .
N5 C1 Ir1 125.9(3) . .
C4 C3 N2 107.5(4) . .
C4 C3 H3 126.3 . .
N2 C3 H3 126.3 . .
C3 C4 N5 106.6(4) . .
C3 C4 H4 126.7 . .
N5 C4 H4 126.7 . .
C7 C6 C11 121.8(4) . .
C7 C6 N5 117.3(4) . .
C11 C6 N5 120.7(4) . .
C8 C7 C6 117.9(4) . .
C8 C7 C12 119.6(4) . .
C6 C7 C12 122.3(4) . .
C9 C8 C7 121.0(5) . .
C9 C8 H8 119.5 . .
C7 C8 H8 119.5 . .
C8 C9 C10 120.2(5) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
C9 C10 C11 121.3(5) . .
C9 C10 H10 119.3 . .
C11 C10 H10 119.3 . .
C10 C11 C6 117.7(5) . .
C10 C11 C15 119.6(4) . .
C6 C11 C15 122.5(4) . .
C7 C12 C13 114.0(4) . .
C7 C12 C14 109.1(4) . .
C13 C12 C14 110.2(4) . .
C7 C12 H12 107.8 . .
C13 C12 H12 107.8 . .
C14 C12 H12 107.8 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C11 C15 C17 113.0(5) . .
C11 C15 C16 109.5(4) . .
C17 C15 C16 110.1(4) . .
C11 C15 H15 108.0 . .
C17 C15 H15 108.0 . .
C16 C15 H15 108.0 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C23 C18 C19 122.5(4) . .
C23 C18 N2 118.6(4) . .
C19 C18 N2 118.5(4) . .
C20 C19 C18 117.0(4) . .
C20 C19 C24 120.8(4) . .
C18 C19 C24 122.0(4) . .
C21 C20 C19 121.6(5) . .
C21 C20 H20 119.2 . .
C19 C20 H20 119.2 . .
C20 C21 C22 120.0(5) . .
C20 C21 H21 120.0 . .
C22 C21 H21 120.0 . .
C21 C22 C23 121.2(5) . .
C21 C22 H22 119.4 . .
C23 C22 H22 119.4 . .
C22 C23 C18 117.5(5) . .
C22 C23 C27 119.2(4) . .
C18 C23 C27 123.2(4) . .
C19 C24 C26 113.8(4) . .
C19 C24 C25 109.6(4) . .
C26 C24 C25 108.8(4) . .
C19 C24 H24 108.2 . .
C26 C24 H24 108.2 . .
C25 C24 H24 108.2 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C23 C27 C29 110.2(4) . .
C23 C27 C28 112.1(4) . .
C29 C27 C28 108.7(4) . .
C23 C27 H27 108.6 . .
C29 C27 H27 108.6 . .
C28 C27 H27 108.6 . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C27 C29 H29A 109.5 . .
C27 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C27 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C34 C30 C31 110.7(4) . .
C34 C30 Ir1 113.8(3) . .
C31 C30 Ir1 133.9(3) . .
C32 C31 C30 113.2(5) . .
C32 C31 H31 123.4 . .
C30 C31 H31 123.4 . .
C31 C32 S33 112.5(4) . .
C31 C32 H32 123.8 . .
S33 C32 H32 123.8 . .
C30 C34 C35 120.7(4) . .
C30 C34 S33 112.8(4) . .
C35 C34 S33 126.1(4) . .
N36 C35 C40 121.0(5) . .
N36 C35 C34 113.2(4) . .
C40 C35 C34 125.7(5) . .
N36 C37 C38 123.0(5) . .
N36 C37 H37 118.5 . .
C38 C37 H37 118.5 . .
C39 C38 C37 118.4(5) . .
C39 C38 H38 120.8 . .
C37 C38 H38 120.8 . .
C40 C39 C38 119.8(5) . .
C40 C39 H39 120.1 . .
C38 C39 H39 120.1 . .
C39 C40 C35 119.5(5) . .
C39 C40 H40 120.2 . .
C35 C40 H40 120.2 . .
N41 C42 C43 123.5(4) . .
N41 C42 H42 118.2 . .
C43 C42 H42 118.2 . .
C44 C43 C42 119.2(5) . .
C44 C43 H43 120.4 . .
C42 C43 H43 120.4 . .
C43 C44 C45 118.3(4) . .
C43 C44 H44 120.8 . .
C45 C44 H44 120.8 . .
C46 C45 C44 118.8(4) . .
C46 C45 H45 120.6 . .
C44 C45 H45 120.6 . .
N41 C46 C45 123.8(4) . .
N41 C46 H46 118.1 . .
C45 C46 H46 118.1 . .
N47 C48 C49 123.3(5) . .
N47 C48 H48 118.3 . .
C49 C48 H48 118.3 . .
C48 C49 C50 119.0(6) . .
C48 C49 H49 120.5 . .
C50 C49 H49 120.5 . .
C51 C50 C49 118.4(5) . .
C51 C50 H50 120.8 . .
C49 C50 H50 120.8 . .
C50 C51 C52 119.5(5) . .
C50 C51 H51 120.3 . .
C52 C51 H51 120.3 . .
N47 C52 C51 122.8(5) . .
N47 C52 H52 118.6 . .
C51 C52 H52 118.6 . .
C1 N2 C3 111.3(4) . .
C1 N2 C18 128.1(4) . .
C3 N2 C18 120.2(4) . .
C1 N5 C4 111.7(4) . .
C1 N5 C6 126.8(3) . .
C4 N5 C6 119.3(4) . .
C37 N36 C35 118.3(4) . .
C37 N36 Ir1 128.5(3) . .
C35 N36 Ir1 112.2(3) . .
C46 N41 C42 116.4(4) . .
C46 N41 Ir1 125.3(3) . .
C42 N41 Ir1 118.0(3) . .
C52 N47 C48 117.0(4) . .
C52 N47 Ir1 121.6(4) . .
C48 N47 Ir1 120.6(3) . .
C32 S33 C34 90.8(3) . .
C1 Ir1 C30 97.21(17) . .
C1 Ir1 N41 170.95(15) . .
C30 Ir1 N41 83.69(16) . .
C1 Ir1 N47 92.20(15) . .
C30 Ir1 N47 170.58(16) . .
N41 Ir1 N47 86.97(14) . .
C1 Ir1 N36 100.97(15) . .
C30 Ir1 N36 79.16(17) . .
N41 Ir1 N36 88.05(13) . .
N47 Ir1 N36 99.36(15) . .
C1 Ir1 H1 85.0(16) . .
C30 Ir1 H1 94.0(16) . .
N41 Ir1 H1 86.0(16) . .
N47 Ir1 H1 86.5(16) . .
N36 Ir1 H1 171.4(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1A F4A 1.335(11) .
B1A F2A 1.345(11) .
B1A F3A 1.357(11) .
B1A F1A 1.358(11) .
B1B F4B 1.397(12) .
B1B F3B 1.406(13) .
B1B F2B 1.409(13) .
B1B F1B 1.415(12) .
C1SA Cl2A 1.871(13) .
C1SA Cl1A 1.962(14) .
C1SA H1S1 0.9900 .
C1SA H1S2 0.9900 .
C1SB Cl1B 1.877(17) .
C1SB Cl2B 1.929(17) .
C1SB H1S3 0.9900 .
C1SB H1S4 0.9900 .
Cl4 Cl3 1.181(9) .
Cl4 C2S 1.715(19) .
C2S Cl3 1.790(19) 3_675
C2S H2S1 0.9900 .
C2S H2S2 0.9900 .
Cl3 C2S 1.790(19) 3_675
Cl3 Cl3 1.836(16) 3_675
C1 N2 1.375(5) .
C1 N5 1.382(5) .
C1 Ir1 2.007(4) .
C3 C4 1.339(6) .
C3 N2 1.393(5) .
C3 H3 0.9500 .
C4 N5 1.392(5) .
C4 H4 0.9500 .
C6 C7 1.402(6) .
C6 C11 1.404(6) .
C6 N5 1.447(6) .
C7 C8 1.398(7) .
C7 C12 1.520(7) .
C8 C9 1.373(8) .
C8 H8 0.9500 .
C9 C10 1.384(8) .
C9 H9 0.9500 .
C10 C11 1.388(7) .
C10 H10 0.9500 .
C11 C15 1.514(7) .
C12 C13 1.522(7) .
C12 C14 1.543(7) .
C12 H12 1.0000 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C17 1.528(7) .
C15 C16 1.540(7) .
C15 H15 1.0000 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C23 1.402(6) .
C18 C19 1.406(7) .
C18 N2 1.451(6) .
C19 C20 1.395(7) .
C19 C24 1.516(7) .
C20 C21 1.380(8) .
C20 H20 0.9500 .
C21 C22 1.384(8) .
C21 H21 0.9500 .
C22 C23 1.394(7) .
C22 H22 0.9500 .
C23 C27 1.509(7) .
C24 C26 1.534(7) .
C24 C25 1.538(7) .
C24 H24 1.0000 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 C29 1.534(7) .
C27 C28 1.537(6) .
C27 H27 1.0000 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 C34 1.381(6) .
C30 C31 1.424(6) .
C30 Ir1 2.013(4) .
C31 C32 1.369(7) .
C31 H31 0.9500 .
C32 S33 1.714(6) .
C32 H32 0.9500 .
C34 C35 1.438(7) .
C34 S33 1.731(5) .
C35 N36 1.367(6) .
C35 C40 1.403(7) .
C37 N36 1.347(6) .
C37 C38 1.390(7) .
C37 H37 0.9500 .
C38 C39 1.383(9) .
C38 H38 0.9500 .
C39 C40 1.371(8) .
C39 H39 0.9500 .
C40 H40 0.9500 .
C42 N41 1.344(6) .
C42 C43 1.385(6) .
C42 H42 0.9500 .
C43 C44 1.373(7) .
C43 H43 0.9500 .
C44 C45 1.386(7) .
C44 H44 0.9500 .
C45 C46 1.383(7) .
C45 H45 0.9500 .
C46 N41 1.339(6) .
C46 H46 0.9500 .
C48 N47 1.351(6) .
C48 C49 1.379(7) .
C48 H48 0.9500 .
C49 C50 1.388(8) .
C49 H49 0.9500 .
C50 C51 1.376(9) .
C50 H50 0.9500 .
C51 C52 1.387(7) .
C51 H51 0.9500 .
C52 N47 1.347(6) .
C52 H52 0.9500 .
N36 Ir1 2.195(4) .
N41 Ir1 2.146(4) .
N47 Ir1 2.176(4) .
Ir1 H1 1.599(10) .
