#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/37/4083790.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_4083790
loop_
_publ_author_name
'Ben-Ari, Eyal'
'Cohen, Revital'
'Gandelman, Mark'
'Shimon, Linda J. W.'
'Martin, Jan M. L.'
'Milstein, David'
_publ_section_title
;
 orthoC−H Activation of Haloarenes and Anisole by an Electron-Rich
 Iridium(I) Complex:  Mechanism and Origin of Regio-
 and Chemoselectivity. An Experimental
 and Theoretical Study
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              3190
_journal_paper_doi               10.1021/om060078+
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C31.5 H34.5 B0.5 F12 Ir0.5 N0.5 P'
_chemical_formula_weight         780.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.5870(19)
_cell_length_b                   13.5870(19)
_cell_length_c                   35.221(7)
_cell_measurement_temperature    120(2)
_cell_volume                     6502.0(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3249
_diffrn_reflns_theta_full        24.73
_diffrn_reflns_theta_max         24.73
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    2.212
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3128
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.486(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0321P)²+7.8361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0653
_reflns_number_gt                3022
_reflns_number_total             3249
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om060078%2Bsi20060124_073905.cif
_cod_data_source_block           m289
_cod_original_formula_sum        'C31.50 H34.50 B0.50 F12 Ir0.50 N0.50 P'
_cod_database_code               4083790
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.531856(15) 0.531856(15) 0.0000 0.02798(10) Uani 1 2 d S . .
P4 P 0.61002(11) 0.41079(13) 0.03626(4) 0.0316(4) Uani 1 1 d . A .
C41 C 0.6590(4) 0.3052(4) 0.00601(18) 0.0381(15) Uani 1 1 d . . .
C42 C 0.7677(5) 0.3154(6) -0.0003(2) 0.068(2) Uani 1 1 d . A .
H42A H 0.8028 0.2999 0.0232 0.103 Uiso 1 1 calc R . .
H42B H 0.7827 0.3831 -0.0080 0.103 Uiso 1 1 calc R . .
H42C H 0.7885 0.2700 -0.0204 0.103 Uiso 1 1 calc R . .
C43 C 0.6108(6) 0.3122(7) -0.0335(2) 0.072(3) Uani 1 1 d . A .
H43A H 0.6162 0.3798 -0.0430 0.109 Uiso 1 1 calc R . .
H43B H 0.5412 0.2938 -0.0316 0.109 Uiso 1 1 calc R . .
H43C H 0.6444 0.2674 -0.0510 0.109 Uiso 1 1 calc R . .
C44 C 0.6310(7) 0.2040(6) 0.0228(3) 0.074(3) Uani 1 1 d . A .
H44A H 0.6536 0.1517 0.0057 0.111 Uiso 1 1 calc R . .
H44B H 0.5594 0.2000 0.0256 0.111 Uiso 1 1 calc R . .
H44C H 0.6623 0.1960 0.0476 0.111 Uiso 1 1 calc R . .
C45 C 0.6882(5) 0.4278(5) 0.08033(15) 0.0370(15) Uani 1 1 d . . .
C46 C 0.7887(4) 0.4748(6) 0.07179(16) 0.0440(16) Uani 1 1 d . A .
H46A H 0.8276 0.4781 0.0952 0.066 Uiso 1 1 calc R . .
H46B H 0.7789 0.5414 0.0618 0.066 Uiso 1 1 calc R . .
H46C H 0.8237 0.4349 0.0529 0.066 Uiso 1 1 calc R . .
C47 C 0.6299(5) 0.4958(5) 0.10719(15) 0.0423(16) Uani 1 1 d . A .
H47A H 0.5801 0.4573 0.1207 0.063 Uiso 1 1 calc R . .
H47B H 0.5975 0.5476 0.0923 0.063 Uiso 1 1 calc R . .
H47C H 0.6750 0.5259 0.1255 0.063 Uiso 1 1 calc R . .
C48 C 0.7079(6) 0.3314(5) 0.1011(2) 0.061(2) Uani 1 1 d . A .
H48A H 0.7517 0.2902 0.0857 0.091 Uiso 1 1 calc R . .
H48B H 0.6456 0.2968 0.1053 0.091 Uiso 1 1 calc R . .
H48C H 0.7393 0.3453 0.1256 0.091 Uiso 1 1 calc R . .
N5 N 0.4224(3) 0.4224(3) 0.0000 0.0216(12) Uani 1 2 d S A .
C10 C 0.4963(4) 0.3608(5) 0.05766(16) 0.0377(15) Uani 1 1 d . . .
H10A H 0.5095 0.2951 0.0687 0.045 Uiso 1 1 calc R A .
H10B H 0.4736 0.4048 0.0783 0.045 Uiso 1 1 calc R . .
C11 C 0.4192(4) 0.3530(4) 0.02821(15) 0.0298(12) Uani 1 1 d . A .
C12 C 0.3447(5) 0.2835(5) 0.0285(2) 0.0433(16) Uani 1 1 d . . .
H12 H 0.3401 0.2386 0.0491 0.052 Uiso 1 1 calc R A .
C13 C 0.2786(4) 0.2786(4) 0.0000 0.045(2) Uani 1 2 d S A .
H13 H 0.2292 0.2292 0.0000 0.054 Uiso 1 2 calc SR . .
C1A C 0.5944(9) 0.6800(9) 0.0077(4) 0.030(4) Uiso 0.505(16) 1 d P A 1
H1A H 0.5739 0.7339 -0.0100 0.036 Uiso 0.505(16) 1 calc PR A 1
C2A C 0.6397(9) 0.7065(10) 0.0453(4) 0.035(4) Uani 0.505(16) 1 d P A 1
H2A1 H 0.6918 0.6591 0.0526 0.042 Uiso 0.505(16) 1 calc PR A 1
H2A2 H 0.5895 0.7090 0.0657 0.042 Uiso 0.505(16) 1 calc PR A 1
C1B C 0.6323(9) 0.6418(10) 0.0221(3) 0.026(3) Uiso 0.495(16) 1 d P A 2
H1B H 0.6882 0.6213 0.0387 0.031 Uiso 0.495(16) 1 calc PR A 2
C2B C 0.5969(10) 0.7450(9) 0.0228(3) 0.030(4) Uani 0.495(16) 1 d P A 2
H2B1 H 0.5401 0.7510 0.0403 0.036 Uiso 0.495(16) 1 calc PR A 2
H2B2 H 0.5755 0.7653 -0.0029 0.036 Uiso 0.495(16) 1 calc PR A 2
C3 C 0.6850(6) 0.8139(6) 0.0370(2) 0.070(3) Uani 1 1 d . . .
H3A H 0.6287 0.8596 0.0341 0.084 Uiso 1 1 calc R A 1
H3B H 0.7208 0.8344 0.0602 0.084 Uiso 1 1 calc R A 1
C4 C 0.7535(5) 0.8322(5) 0.0035(3) 0.060(2) Uani 1 1 d . A .
H4A H 0.7870 0.8960 0.0075 0.072 Uiso 1 1 calc R . .
H4B H 0.7130 0.8384 -0.0197 0.072 Uiso 1 1 calc R . .
B1 B 0.0450(4) 0.0450(4) 0.0000 0.0192(15) Uani 1 2 d S . .
C50 C -0.0001(3) -0.0139(4) 0.03685(12) 0.0205(10) Uani 1 1 d . . .
C51 C -0.0805(4) 0.0220(4) 0.05738(13) 0.0216(11) Uani 1 1 d . . .
H51 H -0.1075 0.0842 0.0507 0.026 Uiso 1 1 calc R . .
C52 C -0.1226(4) -0.0309(4) 0.08746(14) 0.0249(12) Uani 1 1 d . . .
C53 C -0.2054(4) 0.0137(5) 0.10883(15) 0.0312(14) Uani 1 1 d . . .
F53A F -0.2764(3) 0.0461(4) 0.08732(10) 0.0561(12) Uani 1 1 d . . .
F53B F -0.2477(4) -0.0462(4) 0.13292(14) 0.100(2) Uani 1 1 d . . .
F53C F -0.1765(3) 0.0911(4) 0.12854(15) 0.102(2) Uani 1 1 d . . .
C54 C -0.0852(4) -0.1223(4) 0.09771(16) 0.0335(15) Uani 1 1 d . . .
H54 H -0.1129 -0.1577 0.1184 0.040 Uiso 1 1 calc R . .
C55 C -0.0075(4) -0.1610(4) 0.07748(16) 0.0331(15) Uani 1 1 d . . .
C56 C 0.0343(7) -0.2577(5) 0.0877(2) 0.0495(18) Uani 1 1 d . . .
F56A F 0.0416(5) -0.3186(3) 0.05913(15) 0.0989(19) Uani 1 1 d . . .
F56B F -0.0098(5) -0.3029(4) 0.11461(19) 0.146(3) Uani 1 1 d . . .
F56C F 0.1291(5) -0.2529(4) 0.09817(19) 0.115(2) Uani 1 1 d . . .
C57 C 0.0341(5) -0.1084(4) 0.04772(13) 0.0256(11) Uani 1 1 d . . .
H57 H 0.0875 -0.1368 0.0341 0.031 Uiso 1 1 calc R . .
C60 C 0.0310(3) 0.1647(3) 0.00372(13) 0.0190(9) Uani 1 1 d . . .
C61 C 0.0412(4) 0.2132(4) 0.03874(14) 0.0193(11) Uani 1 1 d . . .
H61 H 0.0503 0.1748 0.0610 0.023 Uiso 1 1 calc R . .
C62 C 0.0386(4) 0.3153(4) 0.04209(14) 0.0226(11) Uani 1 1 d . . .
C63 C 0.0525(5) 0.3600(4) 0.08060(18) 0.0371(17) Uani 1 1 d . . .
F63A F 0.0364(3) 0.4568(2) 0.08123(9) 0.0504(10) Uani 1 1 d . . .
F63B F 0.1463(3) 0.3467(3) 0.09241(10) 0.0482(10) Uani 1 1 d . . .
F63C F -0.0042(3) 0.3195(3) 0.10695(9) 0.0494(11) Uani 1 1 d . . .
C64 C 0.0236(4) 0.3740(4) 0.01046(13) 0.0228(11) Uani 1 1 d . . .
H64 H 0.0212 0.4436 0.0127 0.027 Uiso 1 1 calc R . .
C65 C 0.0121(4) 0.3288(4) -0.02462(14) 0.0220(12) Uani 1 1 d . . .
C66 C -0.0044(5) 0.3899(4) -0.05930(16) 0.0345(15) Uani 1 1 d . . .
F66A F -0.0289(5) 0.4803(3) -0.05198(10) 0.0922(18) Uani 1 1 d . . .
F66B F -0.0758(3) 0.3527(4) -0.08162(12) 0.0697(14) Uani 1 1 d . . .
F66C F 0.0732(3) 0.3913(4) -0.08179(11) 0.0669(14) Uani 1 1 d . . .
C67 C 0.0161(4) 0.2260(4) -0.02748(14) 0.0202(11) Uani 1 1 d . . .
H67 H 0.0082 0.1968 -0.0518 0.024 Uiso 1 1 calc R . .
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'
P P 0.1023 0.0942 '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_
_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
N5 Ir1 C1B 158.8(3) . .
N5 Ir1 C1B 158.8(3) . 7
C1B Ir1 C1B 42.3(5) . 7
N5 Ir1 C1A 156.9(3) . 7
C1B Ir1 C1A 37.1(4) . 7
C1B Ir1 C1A 23.5(4) 7 7
N5 Ir1 C1A 156.9(3) . .
C1B Ir1 C1A 23.5(4) . .
C1B Ir1 C1A 37.1(4) 7 .
C1A Ir1 C1A 46.3(6) 7 .
N5 Ir1 P4 79.84(4) . 7
C1B Ir1 P4 109.0(4) . 7
C1B Ir1 P4 90.2(4) 7 7
C1A Ir1 P4 113.7(3) 7 7
C1A Ir1 P4 85.6(3) . 7
N5 Ir1 P4 79.84(4) . .
C1B Ir1 P4 90.2(4) . .
C1B Ir1 P4 109.0(4) 7 .
C1A Ir1 P4 85.6(3) 7 .
C1A Ir1 P4 113.6(3) . .
P4 Ir1 P4 159.69(8) 7 .
C10 P4 C45 100.3(3) . .
C10 P4 C41 104.1(3) . .
C45 P4 C41 110.7(3) . .
C10 P4 Ir1 95.81(19) . .
C45 P4 Ir1 128.1(2) . .
C41 P4 Ir1 112.5(2) . .
C42 C41 C43 106.1(6) . .
C42 C41 C44 112.5(6) . .
C43 C41 C44 107.2(7) . .
C42 C41 P4 110.9(4) . .
C43 C41 P4 108.1(4) . .
C44 C41 P4 111.8(5) . .
C41 C42 H42A 109.5 . .
C41 C42 H42B 109.5 . .
H42A C42 H42B 109.5 . .
C41 C42 H42C 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
C41 C43 H43A 109.5 . .
C41 C43 H43B 109.5 . .
H43A C43 H43B 109.5 . .
C41 C43 H43C 109.5 . .
H43A C43 H43C 109.5 . .
H43B C43 H43C 109.5 . .
C41 C44 H44A 109.5 . .
C41 C44 H44B 109.5 . .
H44A C44 H44B 109.5 . .
C41 C44 H44C 109.5 . .
H44A C44 H44C 109.5 . .
H44B C44 H44C 109.5 . .
C48 C45 C46 107.1(5) . .
C48 C45 C47 108.2(5) . .
C46 C45 C47 109.1(5) . .
C48 C45 P4 112.8(5) . .
C46 C45 P4 112.8(4) . .
C47 C45 P4 106.7(4) . .
C45 C46 H46A 109.5 . .
C45 C46 H46B 109.5 . .
H46A C46 H46B 109.5 . .
C45 C46 H46C 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
C45 C47 H47A 109.5 . .
C45 C47 H47B 109.5 . .
H47A C47 H47B 109.5 . .
C45 C47 H47C 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
C45 C48 H48A 109.5 . .
C45 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
C45 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
C11 N5 C11 118.8(6) 7 .
C11 N5 Ir1 120.6(3) 7 .
C11 N5 Ir1 120.6(3) . .
C11 C10 P4 109.4(4) . .
C11 C10 H10A 109.8 . .
P4 C10 H10A 109.8 . .
C11 C10 H10B 109.8 . .
P4 C10 H10B 109.8 . .
H10A C10 H10B 108.2 . .
N5 C11 C12 119.9(6) . .
N5 C11 C10 115.9(5) . .
C12 C11 C10 124.2(6) . .
C13 C12 C11 121.0(6) . .
C13 C12 H12 119.5 . .
C11 C12 H12 119.5 . .
C12 C13 C12 119.2(8) 7 .
C12 C13 H13 120.4 7 .
C12 C13 H13 120.4 . .
C2A C1A C1A 99.2(11) . 7
C2A C1A Ir1 119.0(9) . .
C1A C1A Ir1 66.9(3) 7 .
C2A C1A H1A 119.1 . .
C1A C1A H1A 119.1 7 .
Ir1 C1A H1A 119.1 . .
C1A C2A C3 102.2(10) . .
C1A C2A H2A1 111.3 . .
C3 C2A H2A1 111.3 . .
C1A C2A H2A2 111.3 . .
C3 C2A H2A2 111.3 . .
H2A1 C2A H2A2 109.2 . .
C2B C1B C1B 97.0(13) . 7
C2B C1B Ir1 117.0(9) . .
C1B C1B Ir1 68.8(3) 7 .
C2B C1B H1B 119.9 . .
C1B C1B H1B 119.9 7 .
Ir1 C1B H1B 119.9 . .
C1B C2B C3 108.5(11) . .
C1B C2B H2B1 110.0 . .
C3 C2B H2B1 110.0 . .
C1B C2B H2B2 110.0 . .
C3 C2B H2B2 110.0 . .
H2B1 C2B H2B2 108.4 . .
C4 C3 C2B 108.2(7) . .
C4 C3 C2A 121.5(7) . .
C2B C3 C2A 40.6(6) . .
C4 C3 H3A 107.0 . .
C2B C3 H3A 75.9 . .
C2A C3 H3A 107.0 . .
C4 C3 H3B 107.0 . .
C2B C3 H3B 142.1 . .
C2A C3 H3B 107.0 . .
H3A C3 H3B 106.7 . .
C3 C4 C4 116.0(8) . 7
C3 C4 H4A 108.3 . .
C4 C4 H4A 108.3 7 .
C3 C4 H4B 108.3 . .
C4 C4 H4B 108.3 7 .
H4A C4 H4B 107.4 . .
C50 B1 C50 105.1(5) . 7
C50 B1 C60 112.1(2) . .
C50 B1 C60 112.1(2) 7 .
C50 B1 C60 112.1(2) . 7
C50 B1 C60 112.1(2) 7 7
C60 B1 C60 103.5(5) . 7
C51 C50 C57 115.6(4) . .
C51 C50 B1 122.0(4) . .
C57 C50 B1 122.1(4) . .
C50 C51 C52 122.1(5) . .
C50 C51 H51 119.0 . .
C52 C51 H51 119.0 . .
C54 C52 C51 120.3(5) . .
C54 C52 C53 120.7(5) . .
C51 C52 C53 118.9(5) . .
F53A C53 F53B 105.1(5) . .
F53A C53 F53C 104.9(6) . .
F53B C53 F53C 106.6(5) . .
F53A C53 C52 113.9(4) . .
F53B C53 C52 114.1(5) . .
F53C C53 C52 111.5(5) . .
C55 C54 C52 119.1(5) . .
C55 C54 H54 120.4 . .
C52 C54 H54 120.4 . .
C54 C55 C57 120.4(5) . .
C54 C55 C56 120.6(5) . .
C57 C55 C56 119.0(5) . .
F56B C56 F56A 107.7(7) . .
F56B C56 F56C 105.6(7) . .
F56A C56 F56C 99.8(7) . .
F56B C56 C55 115.3(6) . .
F56A C56 C55 113.9(6) . .
F56C C56 C55 113.1(6) . .
C55 C57 C50 122.4(5) . .
C55 C57 H57 118.8 . .
C50 C57 H57 118.8 . .
C67 C60 C61 115.3(4) . .
C67 C60 B1 123.1(4) . .
C61 C60 B1 121.5(4) . .
C62 C61 C60 122.6(5) . .
C62 C61 H61 118.7 . .
C60 C61 H61 118.7 . .
C64 C62 C61 120.6(4) . .
C64 C62 C63 120.9(5) . .
C61 C62 C63 118.5(5) . .
F63C C63 F63A 107.6(5) . .
F63C C63 F63B 106.0(5) . .
F63A C63 F63B 106.3(5) . .
F63C C63 C62 113.1(5) . .
F63A C63 C62 113.2(5) . .
F63B C63 C62 110.1(5) . .
C62 C64 C65 118.6(4) . .
C62 C64 H64 120.7 . .
C65 C64 H64 120.7 . .
C64 C65 C67 120.0(4) . .
C64 C65 C66 119.9(5) . .
C67 C65 C66 120.1(5) . .
F66A C66 F66C 108.1(6) . .
F66A C66 F66B 106.6(5) . .
F66C C66 F66B 103.4(5) . .
F66A C66 C65 113.7(5) . .
F66C C66 C65 112.3(5) . .
F66B C66 C65 112.1(5) . .
C60 C67 C65 123.0(4) . .
C60 C67 H67 118.5 . .
C65 C67 H67 118.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 N5 2.103(5) .
Ir1 C1B 2.167(10) .
Ir1 C1B 2.167(10) 7
Ir1 C1A 2.201(12) 7
Ir1 C1A 2.201(12) .
Ir1 P4 2.3375(15) 7
Ir1 P4 2.3376(15) .
P4 C10 1.849(6) .
P4 C45 1.895(6) .
P4 C41 1.907(6) .
C41 C42 1.500(9) .
C41 C43 1.541(9) .
C41 C44 1.544(10) .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
C43 H43A 0.9800 .
C43 H43B 0.9800 .
C43 H43C 0.9800 .
C44 H44A 0.9800 .
C44 H44B 0.9800 .
C44 H44C 0.9800 .
C45 C48 1.523(9) .
C45 C46 1.537(9) .
C45 C47 1.542(8) .
C46 H46A 0.9800 .
C46 H46B 0.9800 .
C46 H46C 0.9800 .
C47 H47A 0.9800 .
C47 H47B 0.9800 .
C47 H47C 0.9800 .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
N5 C11 1.371(6) 7
N5 C11 1.371(6) .
C10 C11 1.478(8) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.383(8) .
C12 C13 1.348(8) .
C12 H12 0.9500 .
C13 C12 1.348(8) 7
C13 H13 0.9500 .
C1A C2A 1.507(19) .
C1A C1A 1.73(2) 7
C1A H1A 1.0000 .
C2A C3 1.611(14) .
C2A H2A1 0.9900 .
C2A H2A2 0.9900 .
C1B C2B 1.48(2) .
C1B C1B 1.56(2) 7
C1B H1B 1.0000 .
C2B C3 1.599(14) .
C2B H2B1 0.9900 .
C2B H2B2 0.9900 .
C3 C4 1.522(11) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C4 1.532(15) 7
C4 H4A 0.9900 .
C4 H4B 0.9900 .
B1 C50 1.643(6) .
B1 C50 1.643(6) 7
B1 C60 1.644(6) .
B1 C60 1.644(6) 7
C50 C51 1.399(6) .
C50 C57 1.418(7) .
C51 C52 1.402(7) .
C51 H51 0.9500 .
C52 C54 1.390(8) .
C52 C53 1.482(7) .
C53 F53A 1.303(7) .
C53 F53B 1.309(7) .
C53 F53C 1.320(7) .
C54 C55 1.379(8) .
C54 H54 0.9500 .
C55 C57 1.388(7) .
C55 C56 1.477(9) .
C56 F56B 1.279(8) .
C56 F56A 1.305(8) .
C56 F56C 1.342(10) .
C57 H57 0.9500 .
C60 C67 1.393(7) .
C60 C61 1.405(7) .
C61 C62 1.393(7) .
C61 H61 0.9500 .
C62 C64 1.385(7) .
C62 C63 1.498(7) .
C63 F63C 1.325(7) .
C63 F63A 1.334(7) .
C63 F63B 1.353(8) .
C64 C65 1.388(7) .
C64 H64 0.9500 .
C65 C67 1.402(7) .
C65 C66 1.493(7) .
C66 F66A 1.299(7) .
C66 F66C 1.319(7) .
C66 F66B 1.348(7) .
C67 H67 0.9500 .
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_4
N5 Ir1 P4 C10 -31.7(2) . .
C1B Ir1 P4 C10 129.5(4) . .
C1B Ir1 P4 C10 168.2(4) 7 .
C1A Ir1 P4 C10 166.3(4) 7 .
C1A Ir1 P4 C10 128.5(4) . .
P4 Ir1 P4 C10 -31.7(2) 7 .
N5 Ir1 P4 C45 -139.7(3) . .
C1B Ir1 P4 C45 21.5(4) . .
C1B Ir1 P4 C45 60.2(4) 7 .
C1A Ir1 P4 C45 58.4(4) 7 .
C1A Ir1 P4 C45 20.6(4) . .
P4 Ir1 P4 C45 -139.7(3) 7 .
N5 Ir1 P4 C41 76.1(2) . .
C1B Ir1 P4 C41 -122.6(4) . .
C1B Ir1 P4 C41 -84.0(4) 7 .
C1A Ir1 P4 C41 -85.8(3) 7 .
C1A Ir1 P4 C41 -123.6(4) . .
P4 Ir1 P4 C41 76.1(2) 7 .
C10 P4 C41 C42 -156.5(5) . .
C45 P4 C41 C42 -49.5(6) . .
Ir1 P4 C41 C42 101.0(5) . .
C10 P4 C41 C43 87.5(5) . .
C45 P4 C41 C43 -165.5(5) . .
Ir1 P4 C41 C43 -15.0(5) . .
C10 P4 C41 C44 -30.2(6) . .
C45 P4 C41 C44 76.8(6) . .
Ir1 P4 C41 C44 -132.7(5) . .
C10 P4 C45 C48 61.5(5) . .
C41 P4 C45 C48 -48.0(6) . .
Ir1 P4 C45 C48 167.3(4) . .
C10 P4 C45 C46 -177.0(5) . .
C41 P4 C45 C46 73.6(5) . .
Ir1 P4 C45 C46 -71.1(5) . .
C10 P4 C45 C47 -57.1(5) . .
C41 P4 C45 C47 -166.6(4) . .
Ir1 P4 C45 C47 48.7(5) . .
C1B Ir1 N5 C11 140.7(11) . 7
C1B Ir1 N5 C11 -39.3(11) 7 7
C1A Ir1 N5 C11 -104.5(9) 7 7
C1A Ir1 N5 C11 75.5(9) . 7
P4 Ir1 N5 C11 23.7(3) 7 7
P4 Ir1 N5 C11 -156.3(3) . 7
C1B Ir1 N5 C11 -39.3(11) . .
C1B Ir1 N5 C11 140.7(11) 7 .
C1A Ir1 N5 C11 75.5(9) 7 .
C1A Ir1 N5 C11 -104.5(9) . .
P4 Ir1 N5 C11 -156.3(3) 7 .
P4 Ir1 N5 C11 23.7(3) . .
C45 P4 C10 C11 173.2(4) . .
C41 P4 C10 C11 -72.2(5) . .
Ir1 P4 C10 C11 42.8(4) . .
C11 N5 C11 C12 -2.2(4) 7 .
Ir1 N5 C11 C12 177.8(4) . .
C11 N5 C11 C10 180.0(6) 7 .
Ir1 N5 C11 C10 0.0(6) . .
P4 C10 C11 N5 -31.9(6) . .
P4 C10 C11 C12 150.3(5) . .
N5 C11 C12 C13 4.5(9) . .
C10 C11 C12 C13 -177.8(5) . .
C11 C12 C13 C12 -2.3(4) . 7
N5 Ir1 C1A C2A 92.1(12) . .
C1B Ir1 C1A C2A -32.6(11) . .
C1B Ir1 C1A C2A -120.8(15) 7 .
C1A Ir1 C1A C2A -87.9(12) 7 .
P4 Ir1 C1A C2A 143.1(9) 7 .
P4 Ir1 C1A C2A -30.2(10) . .
N5 Ir1 C1A C1A 179.995(1) . 7
C1B Ir1 C1A C1A 55.3(10) . 7
C1B Ir1 C1A C1A -32.9(6) 7 7
P4 Ir1 C1A C1A -129.1(8) 7 7
P4 Ir1 C1A C1A 57.7(9) . 7
C1A C1A C2A C3 105.7(8) 7 .
Ir1 C1A C2A C3 174.3(6) . .
N5 Ir1 C1B C2B -92.9(13) . .
C1B Ir1 C1B C2B 87.1(13) 7 .
C1A Ir1 C1B C2B 123.4(14) 7 .
C1A Ir1 C1B C2B 23.7(10) . .
P4 Ir1 C1B C2B 19.1(9) 7 .
P4 Ir1 C1B C2B -154.1(8) . .
N5 Ir1 C1B C1B 179.999(2) . 7
C1A Ir1 C1B C1B 36.3(7) 7 7
C1A Ir1 C1B C1B -63.5(11) . 7
P4 Ir1 C1B C1B -68.1(11) 7 7
P4 Ir1 C1B C1B 118.7(10) . 7
C1B C1B C2B C3 -105.9(9) 7 .
Ir1 C1B C2B C3 -175.7(6) . .
C1B C2B C3 C4 80.0(10) . .
C1B C2B C3 C2A -37.6(9) . .
C1A C2A C3 C4 -52.8(13) . .
C1A C2A C3 C2B 28.4(9) . .
C2B C3 C4 C4 -85.0(9) . 7
C2A C3 C4 C4 -42.4(12) . 7
C50 B1 C50 C51 -91.4(4) 7 .
C60 B1 C50 C51 30.7(6) . .
C60 B1 C50 C51 146.6(4) 7 .
C50 B1 C50 C57 82.7(4) 7 .
C60 B1 C50 C57 -155.2(4) . .
C60 B1 C50 C57 -39.3(6) 7 .
C57 C50 C51 C52 1.8(7) . .
B1 C50 C51 C52 176.3(4) . .
C50 C51 C52 C54 -0.4(8) . .
C50 C51 C52 C53 177.7(5) . .
C54 C52 C53 F53A -131.1(6) . .
C51 C52 C53 F53A 50.8(7) . .
C54 C52 C53 F53B -10.4(8) . .
C51 C52 C53 F53B 171.5(5) . .
C54 C52 C53 F53C 110.5(7) . .
C51 C52 C53 F53C -67.6(7) . .
C51 C52 C54 C55 -1.1(8) . .
C53 C52 C54 C55 -179.2(5) . .
C52 C54 C55 C57 1.2(8) . .
C52 C54 C55 C56 179.8(6) . .
C54 C55 C56 F56B 3.4(11) . .
C57 C55 C56 F56B -178.0(7) . .
C54 C55 C56 F56A 128.6(7) . .
C57 C55 C56 F56A -52.8(10) . .
C54 C55 C56 F56C -118.3(7) . .
C57 C55 C56 F56C 60.3(9) . .
C54 C55 C57 C50 0.3(9) . .
C56 C55 C57 C50 -178.3(6) . .
C51 C50 C57 C55 -1.8(7) . .
B1 C50 C57 C55 -176.2(5) . .
C50 B1 C60 C67 -147.4(4) . .
C50 B1 C60 C67 -29.4(6) 7 .
C60 B1 C60 C67 91.6(5) 7 .
C50 B1 C60 C61 37.6(6) . .
C50 B1 C60 C61 155.6(4) 7 .
C60 B1 C60 C61 -83.4(4) 7 .
C67 C60 C61 C62 -1.2(7) . .
B1 C60 C61 C62 174.1(5) . .
C60 C61 C62 C64 1.3(9) . .
C60 C61 C62 C63 -178.6(5) . .
C64 C62 C63 F63C 130.8(6) . .
C61 C62 C63 F63C -49.4(8) . .
C64 C62 C63 F63A 8.0(9) . .
C61 C62 C63 F63A -172.1(5) . .
C64 C62 C63 F63B -110.8(6) . .
C61 C62 C63 F63B 69.1(7) . .
C61 C62 C64 C65 -0.5(8) . .
C63 C62 C64 C65 179.4(5) . .
C62 C64 C65 C67 -0.2(8) . .
C62 C64 C65 C66 179.9(5) . .
C64 C65 C66 F66A -15.1(8) . .
C67 C65 C66 F66A 165.0(6) . .
C64 C65 C66 F66C 108.1(6) . .
C67 C65 C66 F66C -71.8(7) . .
C64 C65 C66 F66B -136.0(5) . .
C67 C65 C66 F66B 44.1(7) . .
C61 C60 C67 C65 0.5(7) . .
B1 C60 C67 C65 -174.7(5) . .
C64 C65 C67 C60 0.2(8) . .
C66 C65 C67 C60 -179.9(5) . .
