#------------------------------------------------------------------------------
#$Date: 2019-06-25 10:01:56 +0300 (Tue, 25 Jun 2019) $
#$Revision: 216517 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/18/1551876.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_1551876
loop_
_publ_author_name
'Stefan Michlik'
'Rhett Kempe'
_publ_section_title
;
 A sustainable catalytic pyrrole synthesis
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              140
_journal_page_last               144
_journal_paper_doi               10.1038/nchem.1547
_journal_volume                  5
_journal_year                    2013
_chemical_formula_sum            'C33 H47 Ir N5 P2'
_chemical_formula_weight         767.90
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   23.0010(4)
_cell_length_b                   23.0010(4)
_cell_length_c                   17.6210(3)
_cell_measurement_reflns_used    115727
_cell_measurement_temperature    133(2)
_cell_volume                     8073.4(2)
_computing_cell_refinement       X-AREA-STOE
_computing_data_collection       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  STOE-IPDSII
_diffrn_measurement_method       Omega-Scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            57204
_diffrn_reflns_theta_full        25.55
_diffrn_reflns_theta_max         25.55
_diffrn_reflns_theta_min         1.16
_exptl_absorpt_coefficient_mu    3.838
_exptl_absorpt_correction_T_max  0.5425
_exptl_absorpt_correction_T_min  0.2158
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3483
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.067
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.014(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     881
_refine_ls_number_reflns         19972
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0303
_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)+(0.0414P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0647
_reflns_number_gt                18848
_reflns_number_total             19972
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            nchem.1547-s3.cif
_cod_data_source_block           t356hpma
_cod_original_sg_symbol_H-M      P3(2)
_cod_database_code               1551876
_cell_measurement_2theta_min     2.31
_cell_measurement_2theta_max     51.92
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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
C1 C 0.9919(5) 0.9642(5) 0.0427(6) 0.029(2) Uani 1 1 d . . .
C2 C 1.0124(5) 1.0566(5) -0.0243(5) 0.033(2) Uani 1 1 d . . .
C3 C 1.0410(5) 1.1308(5) -0.0286(6) 0.035(2) Uani 1 1 d . . .
C4 C 1.0156(5) 1.1581(4) -0.0795(6) 0.036(2) Uani 1 1 d . . .
H4 H 0.9803 1.1297 -0.1129 0.044 Uiso 1 1 calc R . .
C5 C 1.0419(5) 1.2277(5) -0.0816(7) 0.051(3) Uani 1 1 d . . .
H5 H 1.0226 1.2464 -0.1140 0.061 Uiso 1 1 calc R . .
C6 C 1.0953(6) 1.2684(5) -0.0369(7) 0.054(3) Uani 1 1 d . . .
H6 H 1.1148 1.3157 -0.0411 0.065 Uiso 1 1 calc R . .
C7 C 1.1220(6) 1.2423(5) 0.0147(6) 0.046(3) Uani 1 1 d . . .
H7 H 1.1590 1.2713 0.0458 0.056 Uiso 1 1 calc R . .
C8 C 1.0935(5) 1.1723(5) 0.0200(6) 0.043(3) Uani 1 1 d . . .
H8 H 1.1098 1.1534 0.0564 0.052 Uiso 1 1 calc R . .
C9 C 0.9581(4) 0.9561(4) -0.0816(5) 0.0248(18) Uani 1 1 d . . .
C10 C 0.7794(6) 0.8481(6) -0.1221(8) 0.057(3) Uani 1 1 d . . .
H10A H 0.7309 0.8286 -0.1296 0.085 Uiso 1 1 calc R . .
H10B H 0.8031 0.8921 -0.1470 0.085 Uiso 1 1 calc R . .
H10C H 0.7895 0.8535 -0.0677 0.085 Uiso 1 1 calc R . .
C11 C 0.7532(5) 0.7295(5) -0.1311(7) 0.052(3) Uani 1 1 d . . .
H11A H 0.7527 0.7273 -0.0755 0.078 Uiso 1 1 calc R . .
H11B H 0.7677 0.6992 -0.1516 0.078 Uiso 1 1 calc R . .
H11C H 0.7081 0.7159 -0.1497 0.078 Uiso 1 1 calc R . .
C12 C 0.9010(6) 0.8231(5) 0.1913(7) 0.046(3) Uani 1 1 d . . .
H12 H 0.9282 0.8289 0.2379 0.055 Uiso 1 1 calc R . .
C13 C 0.8456(7) 0.7488(6) 0.1849(7) 0.059(4) Uani 1 1 d . . .
H13A H 0.8168 0.7360 0.2300 0.089 Uiso 1 1 calc R . .
H13B H 0.8663 0.7205 0.1813 0.089 Uiso 1 1 calc R . .
H13C H 0.8185 0.7425 0.1395 0.089 Uiso 1 1 calc R . .
C14 C 0.8681(6) 0.8646(5) 0.1990(7) 0.051(3) Uani 1 1 d . . .
H14A H 0.8493 0.8669 0.1500 0.077 Uiso 1 1 calc R . .
H14B H 0.9014 0.9100 0.2154 0.077 Uiso 1 1 calc R . .
H14C H 0.8321 0.8442 0.2368 0.077 Uiso 1 1 calc R . .
C15 C 1.0845(7) 0.8670(7) 0.0885(8) 0.064(4) Uani 1 1 d . . .
H15A H 1.1229 0.8669 0.1124 0.097 Uiso 1 1 calc R . .
H15B H 1.0960 0.9133 0.0775 0.097 Uiso 1 1 calc R . .
H15C H 1.0731 0.8412 0.0412 0.097 Uiso 1 1 calc R . .
C16 C 1.0037(8) 0.7625(6) 0.1583(8) 0.077(4) Uani 1 1 d . . .
H16A H 0.9932 0.7372 0.1107 0.116 Uiso 1 1 calc R . .
H16B H 0.9639 0.7430 0.1909 0.116 Uiso 1 1 calc R . .
H16C H 1.0403 0.7603 0.1843 0.116 Uiso 1 1 calc R . .
C17 C 0.9997(5) 0.8490(6) -0.2207(8) 0.055(3) Uani 1 1 d . . .
H17A H 1.0187 0.8400 -0.1754 0.082 Uiso 1 1 calc R . .
H17B H 1.0137 0.8968 -0.2226 0.082 Uiso 1 1 calc R . .
H17C H 1.0158 0.8368 -0.2661 0.082 Uiso 1 1 calc R . .
C18 C 0.8993(7) 0.7311(6) -0.2167(7) 0.059(4) Uani 1 1 d . . .
H18A H 0.9226 0.7213 -0.2569 0.088 Uiso 1 1 calc R . .
H18B H 0.8508 0.7051 -0.2253 0.088 Uiso 1 1 calc R . .
H18C H 0.9099 0.7190 -0.1674 0.088 Uiso 1 1 calc R . .
C19 C 0.6872(6) 0.4896(6) 0.5157(7) 0.051(3) Uani 1 1 d . . .
H19A H 0.7083 0.5075 0.4665 0.076 Uiso 1 1 calc R . .
H19B H 0.6939 0.4522 0.5301 0.076 Uiso 1 1 calc R . .
H19C H 0.7074 0.5251 0.5542 0.076 Uiso 1 1 calc R . .
C20 C 0.5996(8) 0.5239(7) 0.5042(10) 0.078(5) Uani 1 1 d . . .
H20A H 0.6241 0.5563 0.5446 0.117 Uiso 1 1 calc R . .
H20B H 0.5514 0.5076 0.5093 0.117 Uiso 1 1 calc R . .
H20C H 0.6152 0.5457 0.4547 0.117 Uiso 1 1 calc R . .
C21 C 0.4443(5) 0.3875(6) 0.4360(7) 0.056(3) Uani 1 1 d . . .
H21A H 0.4443 0.3948 0.3812 0.084 Uiso 1 1 calc R . .
H21B H 0.4636 0.4306 0.4625 0.084 Uiso 1 1 calc R . .
H21C H 0.3980 0.3582 0.4534 0.084 Uiso 1 1 calc R . .
C22 C 0.4563(5) 0.2868(5) 0.4143(7) 0.047(3) Uani 1 1 d . . .
H22A H 0.4073 0.2651 0.4151 0.071 Uiso 1 1 calc R . .
H22B H 0.4703 0.2584 0.4409 0.071 Uiso 1 1 calc R . .
H22C H 0.4720 0.2931 0.3616 0.071 Uiso 1 1 calc R . .
C23 C 0.6318(5) 0.3415(4) 0.3719(6) 0.031(2) Uani 1 1 d . . .
C24 C 0.6796(4) 0.2885(5) 0.3126(5) 0.031(2) Uani 1 1 d . . .
C25 C 0.6654(4) 0.3654(4) 0.2487(5) 0.028(2) Uani 1 1 d . . .
C26 C 0.3930(6) 0.8843(6) 0.1820(7) 0.059(3) Uani 1 1 d . . .
H26A H 0.4282 0.9235 0.1552 0.088 Uiso 1 1 calc R . .
H26B H 0.4083 0.8521 0.1912 0.088 Uiso 1 1 calc R . .
H26C H 0.3834 0.8985 0.2305 0.088 Uiso 1 1 calc R . .
C27 C 0.2937(5) 0.6702(5) 0.3591(6) 0.032(2) Uani 1 1 d . . .
C28 C 0.1851(5) 0.6536(5) 0.0862(7) 0.047(3) Uani 1 1 d . . .
H28A H 0.1691 0.6323 0.1359 0.071 Uiso 1 1 calc R . .
H28B H 0.2220 0.6471 0.0693 0.071 Uiso 1 1 calc R . .
H28C H 0.1482 0.6332 0.0495 0.071 Uiso 1 1 calc R . .
C29 C 0.3215(6) 0.8106(6) 0.4992(7) 0.051(3) Uani 1 1 d . . .
H29A H 0.3401 0.8340 0.4512 0.077 Uiso 1 1 calc R . .
H29B H 0.3385 0.7799 0.5094 0.077 Uiso 1 1 calc R . .
H29C H 0.3349 0.8434 0.5404 0.077 Uiso 1 1 calc R . .
C30 C 0.1486(7) 0.7364(8) 0.1008(9) 0.060(4) Uani 1 1 d . . .
H30A H 0.1176 0.7139 0.0586 0.089 Uiso 1 1 calc R . .
H30B H 0.1630 0.7843 0.1003 0.089 Uiso 1 1 calc R . .
H30C H 0.1260 0.7165 0.1489 0.089 Uiso 1 1 calc R . .
C31 C 0.2157(7) 0.8163(7) 0.4960(9) 0.061(4) Uani 1 1 d . . .
H31A H 0.2339 0.8463 0.5399 0.091 Uiso 1 1 calc R . .
H31B H 0.1667 0.7898 0.5001 0.091 Uiso 1 1 calc R . .
H31C H 0.2279 0.8431 0.4493 0.091 Uiso 1 1 calc R . .
C32 C 0.5394(6) 0.3529(6) 0.0961(7) 0.048(3) Uani 1 1 d . . .
H32A H 0.5200 0.3323 0.1452 0.072 Uiso 1 1 calc R . .
H32B H 0.5683 0.3358 0.0778 0.072 Uiso 1 1 calc R . .
H32C H 0.5033 0.3416 0.0594 0.072 Uiso 1 1 calc R . .
C33 C 0.7731(5) 0.5574(5) 0.2011(7) 0.049(3) Uani 1 1 d . . .
H33A H 0.8126 0.5939 0.1761 0.073 Uiso 1 1 calc R . .
H33B H 0.7819 0.5209 0.2135 0.073 Uiso 1 1 calc R . .
H33C H 0.7636 0.5742 0.2479 0.073 Uiso 1 1 calc R . .
C34 C 0.1141(6) 0.5803(5) 0.4039(7) 0.051(3) Uani 1 1 d . . .
H34A H 0.0709 0.5441 0.4225 0.076 Uiso 1 1 calc R . .
H34B H 0.1496 0.5702 0.4165 0.076 Uiso 1 1 calc R . .
H34C H 0.1119 0.5842 0.3487 0.076 Uiso 1 1 calc R . .
C35 C 0.0750(5) 0.6622(6) 0.4197(8) 0.065(3) Uani 1 1 d . . .
H35A H 0.0743 0.6674 0.3646 0.097 Uiso 1 1 calc R . .
H35B H 0.0847 0.7042 0.4447 0.097 Uiso 1 1 calc R . .
H35C H 0.0311 0.6260 0.4367 0.097 Uiso 1 1 calc R . .
C36 C 0.2999(8) 0.8961(7) 0.1268(10) 0.089(5) Uani 1 1 d . . .
H36A H 0.2878 0.9044 0.1774 0.133 Uiso 1 1 calc R . .
H36B H 0.2596 0.8745 0.0949 0.133 Uiso 1 1 calc R . .
H36C H 0.3329 0.9388 0.1039 0.133 Uiso 1 1 calc R . .
C37 C 0.3612(5) 0.6392(5) 0.2958(5) 0.030(2) Uani 1 1 d . . .
C38 C 0.3235(4) 0.6984(5) 0.2330(5) 0.0279(19) Uani 1 1 d . . .
C39 C 0.6978(6) 0.5871(6) 0.1267(8) 0.060(3) Uani 1 1 d . . .
H39A H 0.6746 0.5949 0.1687 0.090 Uiso 1 1 calc R . .
H39B H 0.6687 0.5726 0.0818 0.090 Uiso 1 1 calc R . .
H39C H 0.7395 0.6287 0.1152 0.090 Uiso 1 1 calc R . .
C40 C 0.5348(6) 0.4578(7) 0.1107(7) 0.052(3) Uani 1 1 d . . .
H40A H 0.5051 0.4432 0.0664 0.078 Uiso 1 1 calc R . .
H40B H 0.5609 0.5069 0.1121 0.078 Uiso 1 1 calc R . .
H40C H 0.5079 0.4411 0.1571 0.078 Uiso 1 1 calc R . .
C41 C 0.8021(5) 0.8016(5) -0.1567(7) 0.042(2) Uani 1 1 d . . .
H41 H 0.7988 0.8033 -0.2132 0.051 Uiso 1 1 calc R . .
C42 C 0.5817(5) 0.4304(5) 0.1054(7) 0.033(3) Uani 1 1 d . . .
H42 H 0.6091 0.4490 0.0582 0.040 Uiso 1 1 calc R . .
C43 C 1.0254(6) 0.8357(5) 0.1413(6) 0.045(3) Uani 1 1 d . . .
H43 H 1.0405 0.8606 0.1904 0.053 Uiso 1 1 calc R . .
C44 C 0.9226(6) 0.8071(5) -0.2175(7) 0.036(2) Uani 1 1 d . . .
H44 H 0.9040 0.8169 -0.2640 0.043 Uiso 1 1 calc R . .
C45 C 0.6120(6) 0.4648(6) 0.5103(7) 0.043(3) Uani 1 1 d . . .
H45 H 0.5895 0.4387 0.5572 0.051 Uiso 1 1 calc R . .
C46 C 0.4862(5) 0.3541(5) 0.4532(6) 0.041(2) Uani 1 1 d . . .
H46 H 0.4845 0.3463 0.5092 0.050 Uiso 1 1 calc R . .
C47 C 0.4676(6) 0.5341(7) 0.2967(7) 0.062(3) Uani 1 1 d . . .
H47 H 0.4893 0.5082 0.2934 0.075 Uiso 1 1 calc R . .
C48 C 0.4899(6) 0.5879(6) 0.2537(7) 0.057(3) Uani 1 1 d . . .
H48 H 0.5302 0.6041 0.2254 0.068 Uiso 1 1 calc R . .
C49 C 0.4528(5) 0.6203(6) 0.2508(6) 0.050(3) Uani 1 1 d . . .
H49 H 0.4652 0.6557 0.2153 0.060 Uiso 1 1 calc R . .
C50 C 0.3991(5) 0.6030(5) 0.2973(5) 0.036(2) Uani 1 1 d . . .
C51 C 0.3793(5) 0.5492(5) 0.3467(6) 0.045(2) Uani 1 1 d . . .
H51 H 0.3426 0.5365 0.3804 0.053 Uiso 1 1 calc R . .
C52 C 0.4152(6) 0.5137(6) 0.3458(7) 0.062(3) Uani 1 1 d . . .
H52 H 0.4029 0.4765 0.3786 0.075 Uiso 1 1 calc R . .
C53 C 0.7142(5) 0.5318(4) 0.1493(6) 0.042(2) Uani 1 1 d . . .
H53 H 0.7272 0.5176 0.1016 0.050 Uiso 1 1 calc R . .
C54 C 0.7009(5) 0.2371(5) 0.3142(5) 0.032(2) Uani 1 1 d . . .
C55 C 0.7549(5) 0.2458(5) 0.2705(5) 0.037(2) Uani 1 1 d . . .
H55 H 0.7766 0.2830 0.2371 0.044 Uiso 1 1 calc R . .
C56 C 0.7773(5) 0.1996(5) 0.2757(6) 0.037(2) Uani 1 1 d . . .
H56 H 0.8151 0.2067 0.2468 0.045 Uiso 1 1 calc R . .
C57 C 0.7452(6) 0.1436(5) 0.3224(6) 0.052(3) Uani 1 1 d . . .
H57 H 0.7594 0.1113 0.3244 0.062 Uiso 1 1 calc R . .
C58 C 0.6924(5) 0.1366(5) 0.3657(6) 0.042(2) Uani 1 1 d . . .
H58 H 0.6707 0.0995 0.3992 0.051 Uiso 1 1 calc R . .
C59 C 0.6696(5) 0.1828(5) 0.3617(6) 0.043(2) Uani 1 1 d . . .
H59 H 0.6326 0.1766 0.3919 0.052 Uiso 1 1 calc R . .
C60 C 0.2442(5) 0.7702(6) 0.4939(8) 0.041(3) Uani 1 1 d . . .
H60 H 0.2278 0.7419 0.5407 0.050 Uiso 1 1 calc R . .
C61 C 0.1291(5) 0.6451(6) 0.4404(6) 0.047(3) Uani 1 1 d . . .
H61 H 0.1284 0.6391 0.4967 0.056 Uiso 1 1 calc R . .
C62 C 0.3292(6) 0.8511(6) 0.1334(6) 0.049(3) Uani 1 1 d . . .
H62 H 0.3421 0.8445 0.0812 0.058 Uiso 1 1 calc R . .
C63 C 0.2095(6) 0.7277(7) 0.0925(7) 0.047(3) Uani 1 1 d . . .
H63 H 0.2330 0.7499 0.0442 0.056 Uiso 1 1 calc R . .
C64 C 0.6475(4) 0.5332(3) 0.7104(5) 0.059(3) Uiso 1 1 d G . .
H64 H 0.6532 0.4955 0.7186 0.071 Uiso 1 1 calc R . .
C65 C 0.5838(3) 0.5257(3) 0.7136(5) 0.073(3) Uiso 1 1 d G . .
H65 H 0.5459 0.4830 0.7239 0.088 Uiso 1 1 calc R . .
C66 C 0.5754(3) 0.5808(3) 0.7016(5) 0.058(3) Uiso 1 1 d G . .
H66 H 0.5318 0.5757 0.7037 0.069 Uiso 1 1 calc R . .
C67 C 0.6308(3) 0.6434(3) 0.6864(5) 0.057(3) Uiso 1 1 d G . .
H67 H 0.6251 0.6810 0.6782 0.068 Uiso 1 1 calc R . .
C68 C 0.6946(3) 0.6508(3) 0.6833(5) 0.065(3) Uiso 1 1 d G . .
H68 H 0.7324 0.6936 0.6729 0.078 Uiso 1 1 calc R . .
C69 C 0.7029(3) 0.5957(4) 0.6953(5) 0.061(3) Uiso 1 1 d G . .
H69 H 0.7465 0.6008 0.6931 0.073 Uiso 1 1 calc R . .
C70 C 0.1973(4) 0.7961(3) 0.7083(5) 0.090(4) Uiso 1 1 d G . .
H70 H 0.1675 0.7492 0.7032 0.108 Uiso 1 1 calc R . .
C71 C 0.2662(4) 0.8219(4) 0.7033(5) 0.060(3) Uiso 1 1 d G . .
H71 H 0.2835 0.7926 0.6948 0.072 Uiso 1 1 calc R . .
C72 C 0.3098(3) 0.8906(4) 0.7108(5) 0.074(3) Uiso 1 1 d G . .
H72 H 0.3569 0.9082 0.7074 0.088 Uiso 1 1 calc R . .
C73 C 0.2845(4) 0.9334(3) 0.7233(6) 0.106(5) Uiso 1 1 d G . .
H73 H 0.3143 0.9803 0.7284 0.127 Uiso 1 1 calc R . .
C74 C 0.2156(5) 0.9076(4) 0.7283(6) 0.093(4) Uiso 1 1 d G . .
H74 H 0.1982 0.9369 0.7368 0.111 Uiso 1 1 calc R . .
C75 C 0.1720(3) 0.8389(5) 0.7208(6) 0.081(4) Uiso 1 1 d G . .
H75 H 0.1249 0.8213 0.7242 0.097 Uiso 1 1 calc R . .
C76 C 0.5897(3) 0.0783(4) 0.5541(6) 0.078(3) Uiso 1 1 d G . .
H76 H 0.6371 0.1028 0.5486 0.093 Uiso 1 1 calc R . .
C77 C 0.5553(4) 0.0087(4) 0.5499(6) 0.074(3) Uiso 1 1 d G . .
H77 H 0.5792 -0.0145 0.5415 0.089 Uiso 1 1 calc R . .
C78 C 0.4859(4) -0.0271(3) 0.5580(5) 0.075(3) Uiso 1 1 d G . .
H78 H 0.4624 -0.0747 0.5551 0.090 Uiso 1 1 calc R . .
C79 C 0.4509(3) 0.0068(4) 0.5702(5) 0.080(4) Uiso 1 1 d G . .
H79 H 0.4034 -0.0177 0.5757 0.096 Uiso 1 1 calc R . .
C80 C 0.4852(4) 0.0765(4) 0.5744(6) 0.086(4) Uiso 1 1 d G . .
H80 H 0.4613 0.0996 0.5827 0.103 Uiso 1 1 calc R . .
C81 C 0.5546(4) 0.1122(3) 0.5663(5) 0.064(3) Uiso 1 1 d G . .
H81 H 0.5781 0.1599 0.5692 0.077 Uiso 1 1 calc R . .
C82 C 0.9606(4) 0.7725(3) 0.5797(5) 0.068(3) Uiso 1 1 d G . .
H82 H 0.9692 0.8174 0.5786 0.081 Uiso 1 1 calc R . .
C83 C 0.8953(3) 0.7194(4) 0.5714(5) 0.077(4) Uiso 1 1 d G . .
H83 H 0.8594 0.7280 0.5647 0.092 Uiso 1 1 calc R . .
C84 C 0.8827(3) 0.6537(3) 0.5730(6) 0.077(4) Uiso 1 1 d G . .
H84 H 0.8381 0.6174 0.5674 0.093 Uiso 1 1 calc R . .
C85 C 0.9353(4) 0.6410(3) 0.5828(6) 0.081(4) Uiso 1 1 d G . .
H85 H 0.9267 0.5961 0.5839 0.097 Uiso 1 1 calc R . .
C86 C 1.0006(4) 0.6941(4) 0.5911(6) 0.082(4) Uiso 1 1 d G . .
H86 H 1.0366 0.6854 0.5978 0.099 Uiso 1 1 calc R . .
C87 C 1.0132(3) 0.7598(4) 0.5896(6) 0.084(4) Uiso 1 1 d G . .
H87 H 1.0578 0.7961 0.5952 0.101 Uiso 1 1 calc R . .
C88 C 0.0387(4) 0.6652(4) 0.9176(6) 0.103(5) Uiso 1 1 d G . .
H88 H -0.0060 0.6295 0.9248 0.123 Uiso 1 1 calc R . .
C89 C 0.0902(5) 0.6513(4) 0.9049(6) 0.079(4) Uiso 1 1 d G . .
H89 H 0.0806 0.6060 0.9035 0.094 Uiso 1 1 calc R . .
C90 C 0.1555(4) 0.7035(5) 0.8944(6) 0.091(4) Uiso 1 1 d G . .
H90 H 0.1907 0.6939 0.8857 0.110 Uiso 1 1 calc R . .
C91 C 0.1695(4) 0.7696(4) 0.8965(7) 0.115(5) Uiso 1 1 d G . .
H91 H 0.2142 0.8053 0.8893 0.138 Uiso 1 1 calc R . .
C92 C 0.1181(5) 0.7836(4) 0.9091(6) 0.097(5) Uiso 1 1 d G . .
H92 H 0.1276 0.8288 0.9106 0.116 Uiso 1 1 calc R . .
C93 C 0.0527(5) 0.7314(5) 0.9197(6) 0.090(4) Uiso 1 1 d G . .
H93 H 0.0175 0.7409 0.9283 0.108 Uiso 1 1 calc R . .
C94 C 0.8754(6) 0.7901(3) 0.3895(7) 0.107(5) Uiso 1 1 d G . .
H94 H 0.9002 0.8377 0.3919 0.128 Uiso 1 1 calc R . .
C95 C 0.9086(4) 0.7540(4) 0.3801(6) 0.092(4) Uiso 1 1 d G . .
H95 H 0.9561 0.7770 0.3759 0.111 Uiso 1 1 calc R . .
C96 C 0.8722(5) 0.6843(4) 0.3767(6) 0.093(4) Uiso 1 1 d G . .
H96 H 0.8949 0.6597 0.3702 0.112 Uiso 1 1 calc R . .
C97 C 0.8027(5) 0.6507(3) 0.3828(6) 0.076(3) Uiso 1 1 d G . .
H97 H 0.7778 0.6030 0.3805 0.091 Uiso 1 1 calc R . .
C98 C 0.7695(4) 0.6867(5) 0.3922(6) 0.112(5) Uiso 1 1 d G . .
H98 H 0.7219 0.6637 0.3964 0.134 Uiso 1 1 calc R . .
C99 C 0.8058(6) 0.7564(5) 0.3956(7) 0.117(6) Uiso 1 1 d G . .
H99 H 0.7831 0.7810 0.4021 0.140 Uiso 1 1 calc R . .
N1 N 0.9606(4) 0.9234(4) -0.0174(4) 0.0296(16) Uani 1 1 d . . .
N2 N 0.9843(4) 1.0228(4) -0.0871(5) 0.0306(17) Uani 1 1 d . . .
N3 N 1.0196(3) 1.0322(3) 0.0418(5) 0.0269(16) Uani 1 1 d . . .
N4 N 0.9277(4) 0.9151(4) -0.1430(4) 0.0297(17) Uani 1 1 d . . .
H4A H 0.9276 0.9328 -0.1873 0.036 Uiso 1 1 calc . . .
N5 N 0.9946(4) 0.9327(4) 0.1049(5) 0.0323(18) Uani 1 1 d . . .
H5A H 1.0158 0.9562 0.1453 0.039 Uiso 1 1 calc . . .
N6 N 0.2919(4) 0.7002(4) 0.2959(5) 0.0315(17) Uani 1 1 d . . .
N7 N 0.3590(4) 0.6676(4) 0.2310(5) 0.0327(17) Uani 1 1 d . . .
N8 N 0.3297(4) 0.6385(4) 0.3614(5) 0.0280(16) Uani 1 1 d . . .
N9 N 0.3177(4) 0.7295(4) 0.1702(5) 0.0336(18) Uani 1 1 d . . .
H9 H 0.3391 0.7305 0.1284 0.040 Uiso 1 1 calc . . .
N10 N 0.2617(4) 0.6743(4) 0.4181(5) 0.0334(18) Uani 1 1 d . . .
H10 H 0.2647 0.6571 0.4615 0.040 Uiso 1 1 calc . . .
N11 N 0.6366(4) 0.3774(4) 0.3096(4) 0.0336(19) Uani 1 1 d . . .
N12 N 0.6871(4) 0.3211(4) 0.2479(5) 0.0286(17) Uani 1 1 d . . .
N13 N 0.6525(4) 0.2967(4) 0.3767(4) 0.0277(16) Uani 1 1 d . . .
N14 N 0.6703(4) 0.4024(4) 0.1849(5) 0.0310(18) Uani 1 1 d . . .
H14 H 0.6891 0.3980 0.1435 0.037 Uiso 1 1 calc . . .
N15 N 0.6058(4) 0.3548(4) 0.4335(5) 0.0311(17) Uani 1 1 d . . .
H15 H 0.6045 0.3357 0.4773 0.037 Uiso 1 1 calc . . .
P1 P 0.88910(13) 0.82826(12) -0.13308(14) 0.0328(5) Uani 1 1 d . . .
P2 P 0.95640(15) 0.84538(14) 0.10707(15) 0.0355(6) Uani 1 1 d . . .
P3 P 0.26845(15) 0.76760(14) 0.17158(16) 0.0359(6) Uani 1 1 d . . .
P4 P 0.21326(13) 0.71265(14) 0.41332(14) 0.0341(5) Uani 1 1 d . . .
P5 P 0.63988(12) 0.45757(12) 0.18585(14) 0.0330(5) Uani 1 1 d . . .
P6 P 0.57469(13) 0.40947(12) 0.42648(17) 0.0327(6) Uani 1 1 d . . .
Ir1 Ir 0.91608(4) 0.820888(17) -0.012122(15) 0.03438(10) Uani 1 1 d . . .
Ir2 Ir 0.23332(3) 0.74869(3) 0.292513(18) 0.03516(10) Uani 1 1 d . . .
Ir3 Ir 0.602948(17) 0.444914(17) 0.30609(3) 0.03180(7) Uani 1 1 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'
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 C1 N1 114.7(8) . .
N5 C1 N3 120.7(9) . .
N1 C1 N3 124.6(8) . .
N2 C2 N3 127.5(9) . .
N2 C2 C3 115.9(9) . .
N3 C2 C3 116.6(9) . .
C4 C3 C8 120.3(9) . .
C4 C3 C2 120.5(9) . .
C8 C3 C2 119.1(9) . .
C3 C4 C5 119.8(10) . .
C6 C5 C4 119.8(10) . .
C5 C6 C7 121.5(9) . .
C6 C7 C8 119.0(11) . .
C3 C8 C7 119.4(10) . .
N2 C9 N4 120.8(8) . .
N2 C9 N1 124.5(8) . .
N4 C9 N1 114.7(7) . .
C14 C12 C13 108.3(10) . .
C14 C12 P2 113.2(9) . .
C13 C12 P2 108.7(8) . .
N13 C23 N11 125.0(9) . .
N13 C23 N15 119.6(8) . .
N11 C23 N15 115.4(8) . .
N12 C24 N13 125.4(9) . .
N12 C24 C54 117.6(8) . .
N13 C24 C54 117.0(8) . .
N12 C25 N11 124.6(9) . .
N12 C25 N14 121.0(9) . .
N11 C25 N14 114.5(8) . .
N10 C27 N6 117.9(8) . .
N10 C27 N8 122.5(9) . .
N6 C27 N8 119.6(9) . .
N7 C37 N8 125.7(8) . .
N7 C37 C50 118.2(8) . .
N8 C37 C50 116.1(8) . .
N7 C38 N6 121.9(9) . .
N7 C38 N9 120.6(8) . .
N6 C38 N9 117.5(8) . .
C11 C41 C10 108.4(9) . .
C11 C41 P1 112.6(8) . .
C10 C41 P1 111.9(7) . .
C40 C42 C32 108.6(10) . .
C40 C42 P5 111.3(8) . .
C32 C42 P5 113.9(8) . .
C15 C43 C16 111.7(10) . .
C15 C43 P2 111.9(8) . .
C16 C43 P2 112.2(9) . .
C17 C44 C18 110.3(11) . .
C17 C44 P1 111.5(8) . .
C18 C44 P1 109.6(8) . .
C20 C45 C19 110.6(11) . .
C20 C45 P6 109.0(9) . .
C19 C45 P6 110.8(8) . .
C22 C46 C21 110.2(9) . .
C22 C46 P6 111.9(7) . .
C21 C46 P6 110.9(7) . .
C48 C47 C52 123.3(11) . .
C47 C48 C49 118.2(12) . .
C50 C49 C48 122.0(11) . .
C49 C50 C51 118.9(9) . .
C49 C50 C37 121.8(10) . .
C51 C50 C37 119.3(9) . .
C50 C51 C52 118.5(10) . .
C47 C52 C51 118.5(12) . .
C33 C53 C39 112.4(8) . .
C33 C53 P5 113.3(7) . .
C39 C53 P5 111.1(7) . .
C59 C54 C55 119.6(9) . .
C59 C54 C24 120.2(8) . .
C55 C54 C24 120.1(9) . .
C54 C55 C56 119.9(9) . .
C57 C56 C55 121.2(9) . .
C58 C57 C56 117.7(8) . .
C57 C58 C59 121.9(9) . .
C54 C59 C58 119.7(9) . .
C31 C60 C29 110.6(10) . .
C31 C60 P4 112.5(9) . .
C29 C60 P4 113.4(8) . .
C34 C61 C35 110.0(10) . .
C34 C61 P4 110.5(7) . .
C35 C61 P4 111.7(8) . .
C36 C62 C26 110.5(11) . .
C36 C62 P3 112.3(9) . .
C26 C62 P3 110.6(8) . .
C28 C63 C30 108.0(11) . .
C28 C63 P3 112.6(8) . .
C30 C63 P3 111.1(9) . .
C65 C64 C69 120.0 . .
C64 C65 C66 120.0 . .
C67 C66 C65 120.0 . .
C66 C67 C68 120.0 . .
C69 C68 C67 120.0 . .
C68 C69 C64 120.0 . .
C71 C70 C75 120.0 . .
C70 C71 C72 120.0 . .
C73 C72 C71 120.0 . .
C72 C73 C74 120.0 . .
C75 C74 C73 120.0 . .
C74 C75 C70 120.0 . .
C77 C76 C81 120.0 . .
C78 C77 C76 120.0 . .
C77 C78 C79 120.0 . .
C80 C79 C78 120.0 . .
C81 C80 C79 120.0 . .
C80 C81 C76 120.0 . .
C83 C82 C87 120.0 . .
C82 C83 C84 120.0 . .
C83 C84 C85 120.0 . .
C84 C85 C86 120.0 . .
C87 C86 C85 120.0 . .
C86 C87 C82 120.0 . .
C89 C88 C93 120.0 . .
C88 C89 C90 120.0 . .
C91 C90 C89 120.0 . .
C90 C91 C92 120.0 . .
C93 C92 C91 120.0 . .
C92 C93 C88 120.0 . .
C95 C94 C99 120.0 . .
C96 C95 C94 120.0 . .
C97 C96 C95 120.0 . .
C96 C97 C98 120.0 . .
C97 C98 C99 120.0 . .
C98 C99 C94 120.0 . .
C1 N1 C9 114.5(8) . .
C1 N1 Ir1 123.2(6) . .
C9 N1 Ir1 122.2(6) . .
C2 N2 C9 114.9(8) . .
C2 N3 C1 113.9(8) . .
C9 N4 P1 120.0(6) . .
C1 N5 P2 120.7(7) . .
C27 N6 C38 121.6(8) . .
C27 N6 Ir2 119.2(6) . .
C38 N6 Ir2 119.1(7) . .
C38 N7 C37 115.3(8) . .
C27 N8 C37 115.9(8) . .
C38 N9 P3 120.8(7) . .
C27 N10 P4 121.9(7) . .
C23 N11 C25 114.7(8) . .
C23 N11 Ir3 122.9(7) . .
C25 N11 Ir3 122.4(6) . .
C24 N12 C25 115.3(8) . .
C23 N13 C24 115.0(8) . .
C25 N14 P5 120.5(7) . .
C23 N15 P6 119.8(7) . .
N4 P1 C41 101.9(4) . .
N4 P1 C44 100.5(4) . .
C41 P1 C44 105.0(5) . .
N4 P1 Ir1 100.3(3) . .
C41 P1 Ir1 119.3(4) . .
C44 P1 Ir1 125.1(4) . .
N5 P2 C43 100.5(4) . .
N5 P2 C12 102.5(5) . .
C43 P2 C12 102.9(6) . .
N5 P2 Ir1 100.1(3) . .
C43 P2 Ir1 123.8(4) . .
C12 P2 Ir1 122.5(4) . .
N9 P3 C63 104.0(4) . .
N9 P3 C62 100.0(5) . .
C63 P3 C62 103.2(5) . .
N9 P3 Ir2 100.2(3) . .
C63 P3 Ir2 121.3(4) . .
C62 P3 Ir2 124.0(4) . .
N10 P4 C60 102.4(5) . .
N10 P4 C61 103.3(5) . .
C60 P4 C61 105.9(6) . .
N10 P4 Ir2 99.6(3) . .
C60 P4 Ir2 122.4(4) . .
C61 P4 Ir2 119.5(4) . .
N14 P5 C53 98.6(4) . .
N14 P5 C42 103.7(4) . .
C53 P5 C42 103.2(5) . .
N14 P5 Ir3 100.3(3) . .
C53 P5 Ir3 124.8(3) . .
C42 P5 Ir3 121.4(4) . .
N15 P6 C46 101.1(4) . .
N15 P6 C45 102.9(5) . .
C46 P6 C45 104.1(5) . .
N15 P6 Ir3 100.4(3) . .
C46 P6 Ir3 120.7(4) . .
C45 P6 Ir3 123.4(4) . .
N1 Ir1 P1 82.4(2) . .
N1 Ir1 P2 81.3(2) . .
P1 Ir1 P2 163.69(10) . .
N6 Ir2 P3 82.4(2) . .
N6 Ir2 P4 81.2(2) . .
P3 Ir2 P4 163.57(9) . .
N11 Ir3 P5 82.3(2) . .
N11 Ir3 P6 81.2(2) . .
P5 Ir3 P6 163.44(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N5 1.332(13) .
C1 N1 1.358(13) .
C1 N3 1.363(12) .
C2 N2 1.320(13) .
C2 N3 1.339(12) .
C2 C3 1.493(13) .
C3 C4 1.381(14) .
C3 C8 1.397(15) .
C4 C5 1.401(13) .
C5 C6 1.362(17) .
C6 C7 1.390(17) .
C7 C8 1.405(14) .
C9 N2 1.342(11) .
C9 N4 1.374(12) .
C9 N1 1.376(12) .
C10 C41 1.534(15) .
C11 C41 1.534(14) .
C12 C14 1.492(17) .
C12 C13 1.542(16) .
C12 P2 1.854(13) .
C15 C43 1.500(17) .
C16 C43 1.528(15) .
C17 C44 1.539(16) .
C18 C44 1.550(15) .
C19 C45 1.528(16) .
C20 C45 1.526(18) .
C21 C46 1.534(13) .
C22 C46 1.508(15) .
C23 N13 1.336(12) .
C23 N11 1.344(13) .
C23 N15 1.347(13) .
C24 N12 1.328(12) .
C24 N13 1.349(12) .
C24 C54 1.489(13) .
C25 N12 1.339(12) .
C25 N11 1.361(13) .
C25 N14 1.380(12) .
C26 C62 1.534(18) .
C27 N10 1.303(14) .
C27 N6 1.322(13) .
C27 N8 1.350(11) .
C28 C63 1.510(16) .
C29 C60 1.544(15) .
C30 C63 1.516(15) .
C31 C60 1.501(15) .
C32 C42 1.555(15) .
C33 C53 1.489(14) .
C34 C61 1.496(16) .
C35 C61 1.526(14) .
C36 C62 1.495(15) .
C37 N7 1.331(13) .
C37 N8 1.360(12) .
C37 C50 1.476(13) .
C38 N7 1.322(12) .
C38 N6 1.337(12) .
C38 N9 1.360(13) .
C39 C53 1.549(14) .
C40 C42 1.500(15) .
C41 P1 1.823(11) .
C42 P5 1.832(12) .
C43 P2 1.813(11) .
C44 P1 1.849(12) .
C45 P6 1.857(12) .
C46 P6 1.842(10) .
C47 C48 1.318(18) .
C47 C52 1.362(18) .
C48 C49 1.385(14) .
C49 C50 1.366(15) .
C50 C51 1.389(14) .
C51 C52 1.424(14) .
C53 P5 1.825(10) .
C54 C59 1.371(14) .
C54 C55 1.389(14) .
C55 C56 1.394(13) .
C56 C57 1.390(15) .
C57 C58 1.375(14) .
C58 C59 1.402(12) .
C60 P4 1.826(13) .
C61 P4 1.839(11) .
C62 P3 1.847(12) .
C63 P3 1.838(13) .
C64 C65 1.3900 .
C64 C69 1.3900 .
C65 C66 1.3900 .
C66 C67 1.3900 .
C67 C68 1.3900 .
C68 C69 1.3900 .
C70 C71 1.3900 .
C70 C75 1.3900 .
C71 C72 1.3900 .
C72 C73 1.3900 .
C73 C74 1.3900 .
C74 C75 1.3900 .
C76 C77 1.3900 .
C76 C81 1.3900 .
C77 C78 1.3900 .
C78 C79 1.3900 .
C79 C80 1.3900 .
C80 C81 1.3900 .
C82 C83 1.3900 .
C82 C87 1.3900 .
C83 C84 1.3900 .
C84 C85 1.3900 .
C85 C86 1.3900 .
C86 C87 1.3900 .
C88 C89 1.3900 .
C88 C93 1.3900 .
C89 C90 1.3900 .
C90 C91 1.3900 .
C91 C92 1.3900 .
C92 C93 1.3900 .
C94 C95 1.3900 .
C94 C99 1.3900 .
C95 C96 1.3900 .
C96 C97 1.3900 .
C97 C98 1.3900 .
C98 C99 1.3900 .
N1 Ir1 2.049(8) .
N4 P1 1.743(8) .
N5 P2 1.744(8) .
N6 Ir2 2.137(7) .
N9 P3 1.744(8) .
N10 P4 1.734(8) .
N11 Ir3 2.053(8) .
N14 P5 1.728(8) .
N15 P6 1.734(8) .
P1 Ir1 2.250(3) .
P2 Ir1 2.251(3) .
P3 Ir2 2.243(3) .
P4 Ir2 2.247(3) .
P5 Ir3 2.247(2) .
P6 Ir3 2.249(3) .
